# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ea665_6
_database_code_depnum_ccdc_archive 'CCDC 1548702'
_audit_update_record             
;
2017-05-08 deposited with the CCDC.	2020-01-07 downloaded from the CCDC.
;

_audit_creation_date             2017-04-11T23:06:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C49 H65 Cl9 N14 O2'
_chemical_formula_moiety         '2(C23 H31 N7 O), 3(C H Cl3)'
_chemical_formula_weight         1201.2

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.9113(4)
_cell_length_b                   13.8869(4)
_cell_length_c                   16.5533(3)
_cell_angle_alpha                102.178(2)
_cell_angle_beta                 91.521(2)
_cell_angle_gamma                97.504(2)
_cell_volume                     2871.85(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    11344
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.611

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_F_000             1252

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.71536
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.828
_shelx_estimated_absorpt_T_max   0.908

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_ambient_temperature      130(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0008737
_diffrn_orient_matrix_ub_12      -0.0294046
_diffrn_orient_matrix_ub_13      0.0301641
_diffrn_orient_matrix_ub_21      -0.0383369
_diffrn_orient_matrix_ub_22      -0.0365706
_diffrn_orient_matrix_ub_23      -0.0243853
_diffrn_orient_matrix_ub_31      0.0401182
_diffrn_orient_matrix_ub_32      -0.0241328
_diffrn_orient_matrix_ub_33      -0.0205691
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_number            40860
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.053
_diffrn_reflns_theta_max         28.674
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.905
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.905
_reflns_Friedel_coverage         0
_reflns_number_total             13393
_reflns_number_gt                9043
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0848P)²+3.2135P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         13393
_refine_ls_number_parameters     695
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0662
_refine_ls_wR_factor_ref         0.1928
_refine_ls_wR_factor_gt          0.1639
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_restrained_S_all      1.03
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.788
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.079

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl68 Cl 0.70299(9) 0.16223(10) 0.33932(6) 0.0684(3) Uani 1 1 d . . . . .
Cl74 Cl 0.51365(7) 0.90736(7) 0.21384(7) 0.0571(3) Uani 1 1 d . . . . .
Cl3A Cl 0.8813(5) 0.2176(6) 0.1664(4) 0.0834(16) Uani 0.706(11) 1 d . . P A 1
Cl72 Cl 0.32381(7) 0.77104(7) 0.17458(6) 0.0534(2) Uani 1 1 d . . . . .
Cl1A Cl 0.8688(4) 0.2365(3) -0.0020(3) 0.0923(13) Uani 0.706(11) 1 d . . P A 1
Cl69 Cl 0.56359(10) 0.23537(9) 0.46447(8) 0.0734(3) Uani 1 1 d . . . . .
Cl73 Cl 0.44658(8) 0.78003(8) 0.32620(6) 0.0565(3) Uani 1 1 d . . . . .
Cl2A Cl 0.8544(6) 0.0410(3) 0.0359(4) 0.1503(18) Uani 0.706(11) 1 d . . P A 1
Cl70 Cl 0.59455(10) 0.02959(9) 0.43025(9) 0.0773(3) Uani 1 1 d . . . . .
O49 O 0.08042(16) 0.25577(15) 0.33044(13) 0.0355(5) Uani 1 1 d . . . . .
O18 O 0.67231(16) 0.74455(15) 0.15357(13) 0.0335(5) Uani 1 1 d . . . . .
N50 N 0.18771(17) 0.37930(16) 0.29347(13) 0.0244(5) Uani 1 1 d . . . . .
H50 H 0.2394 0.3954 0.2631 0.029 Uiso 1 1 calc R U . . .
N55 N 0.06974(19) 0.69013(19) 0.54966(15) 0.0330(6) Uani 1 1 d . . . . .
H55 H 0.0356 0.6964 0.5954 0.04 Uiso 1 1 calc R U . . .
N19 N 0.72503(16) 0.62490(16) 0.21149(13) 0.0246(5) Uani 1 1 d . . . . .
H19 H 0.7669 0.6104 0.2487 0.03 Uiso 1 1 calc R U . . .
N4 N 0.54719(16) 0.48197(17) 0.27588(13) 0.0247(5) Uani 1 1 d . . . . .
N35 N 0.05210(17) 0.52341(17) 0.22819(14) 0.0258(5) Uani 1 1 d . . . . .
N32 N -0.05050(17) 0.46985(19) 0.31532(14) 0.0289(5) Uani 1 1 d . . . . .
N24 N 0.49119(19) 0.29862(18) -0.02735(15) 0.0322(5) Uani 1 1 d . . . . .
H24 H 0.448 0.2876 -0.0714 0.039 Uiso 1 1 calc R U . . .
N11 N 0.84165(18) 0.76451(18) 0.32925(14) 0.0267(5) Uani 1 1 d . . . . .
N42 N 0.25713(18) 0.24118(18) 0.17213(14) 0.0276(5) Uani 1 1 d . . . . .
N1 N 0.45913(17) 0.53749(18) 0.18634(14) 0.0283(5) Uani 1 1 d . . . . .
N3 N 0.44656(18) 0.47153(19) 0.29565(15) 0.0318(5) Uani 1 1 d . . . . .
N2 N 0.39451(18) 0.5049(2) 0.24178(15) 0.0343(6) Uani 1 1 d . . . . .
N34 N -0.04636(18) 0.53587(19) 0.20642(15) 0.0321(5) Uani 1 1 d . . . . .
N33 N -0.10638(18) 0.5040(2) 0.25896(15) 0.0351(6) Uani 1 1 d . . . . .
C22 C 0.6166(2) 0.3756(2) 0.07075(16) 0.0238(5) Uani 1 1 d . . . . .
C6 C 0.6169(2) 0.4901(2) 0.41840(17) 0.0334(6) Uani 1 1 d . . . . .
H6A H 0.5446 0.4698 0.4329 0.04 Uiso 1 1 calc R U . . .
H6B H 0.6646 0.4596 0.4501 0.04 Uiso 1 1 calc R U . . .
C38 C 0.1149(2) 0.4190(2) 0.05644(18) 0.0366(7) Uani 1 1 d . . . . .
H38A H 0.0824 0.4032 -0.0005 0.044 Uiso 1 1 calc R U . . .
H38B H 0.068 0.3841 0.0907 0.044 Uiso 1 1 calc R U . . .
C54 C 0.1131(2) 0.6077(2) 0.51357(17) 0.0295(6) Uani 1 1 d . . . . .
H54 H 0.1116 0.5489 0.5345 0.035 Uiso 1 1 calc R U . . .
C30 C 0.5767(2) 0.2811(2) 0.08728(16) 0.0253(5) Uani 1 1 d . . . . .
C53 C 0.15914(19) 0.6228(2) 0.44246(16) 0.0246(5) Uani 1 1 d . . . . .
C25 C 0.4985(2) 0.2341(2) 0.02439(17) 0.0272(6) Uani 1 1 d . . . . .
C56 C 0.0876(2) 0.7608(2) 0.50381(17) 0.0288(6) Uani 1 1 d . . . . .
C31 C 0.55420(19) 0.52266(19) 0.20899(15) 0.0226(5) Uani 1 1 d . . . . .
C52 C 0.2137(2) 0.5494(2) 0.38431(16) 0.0249(5) Uani 1 1 d . . . . .
H52A H 0.2705 0.529 0.4154 0.03 Uiso 1 1 calc R U . . .
H52B H 0.2456 0.5817 0.3412 0.03 Uiso 1 1 calc R U . . .
C20 C 0.64882(19) 0.54601(19) 0.16210(15) 0.0224(5) Uani 1 1 d . . . . .
H20 H 0.6235 0.5733 0.1151 0.027 Uiso 1 1 calc R U . . .
C21 C 0.69700(19) 0.4530(2) 0.12260(16) 0.0238(5) Uani 1 1 d . . . . .
H21A H 0.7541 0.4717 0.0877 0.029 Uiso 1 1 calc R U . . .
H21B H 0.7275 0.4252 0.1667 0.029 Uiso 1 1 calc R U . . .
C62 C 0.04754(19) 0.48276(19) 0.29517(16) 0.0225(5) Uani 1 1 d . . . . .
C51 C 0.13686(19) 0.45712(19) 0.34287(15) 0.0225(5) Uani 1 1 d . . . . .
H51 H 0.1053 0.4288 0.3888 0.027 Uiso 1 1 calc R U . . .
C7 C 0.6423(2) 0.6029(2) 0.44501(17) 0.0328(6) Uani 1 1 d . . . . .
H7A H 0.612 0.6249 0.499 0.039 Uiso 1 1 calc R U . . .
H7B H 0.6084 0.6332 0.4041 0.039 Uiso 1 1 calc R U . . .
C37 C 0.1227(3) 0.5301(2) 0.09039(18) 0.0370(7) Uani 1 1 d . . . . .
H37A H 0.0572 0.5529 0.0744 0.044 Uiso 1 1 calc R U . . .
H37B H 0.1807 0.5643 0.0645 0.044 Uiso 1 1 calc R U . . .
C43 C 0.2266(2) 0.2099(2) 0.24861(17) 0.0267(6) Uani 1 1 d . . . . .
C8 C 0.7593(2) 0.6412(2) 0.45302(18) 0.0336(6) Uani 1 1 d . . . . .
H8A H 0.7917 0.6188 0.4994 0.04 Uiso 1 1 calc R U . . .
H8B H 0.7916 0.6115 0.4018 0.04 Uiso 1 1 calc R U . . .
C5 C 0.6264(2) 0.4494(2) 0.32603(17) 0.0289(6) Uani 1 1 d . . . . .
H5A H 0.6971 0.4728 0.3102 0.035 Uiso 1 1 calc R U . . .
H5B H 0.6173 0.3758 0.3147 0.035 Uiso 1 1 calc R U . . .
C61 C 0.1430(2) 0.7201(2) 0.43465(16) 0.0267(6) Uani 1 1 d . . . . .
C58 C 0.0976(3) 0.9153(3) 0.4633(2) 0.0443(8) Uani 1 1 d . . . . .
H58 H 0.0837 0.9821 0.4723 0.053 Uiso 1 1 calc R U . . .
C48 C 0.1569(2) 0.2829(2) 0.29348(16) 0.0255(6) Uani 1 1 d . . . . .
C17 C 0.7328(2) 0.7187(2) 0.20156(16) 0.0238(5) Uani 1 1 d . . . . .
C12 C 0.8251(2) 0.7910(2) 0.24906(16) 0.0252(5) Uani 1 1 d . . . . .
C13 C 0.9262(2) 0.7789(2) 0.20007(18) 0.0305(6) Uani 1 1 d . . . . .
H13A H 0.9747 0.7457 0.2287 0.037 Uiso 1 1 calc R U . . .
H13B H 0.9082 0.7382 0.1435 0.037 Uiso 1 1 calc R U . . .
C63 C 0.8250(3) 0.1642(3) 0.0666(3) 0.0592(10) Uani 1 1 d . . . . .
H63 H 0.7473 0.1615 0.0683 0.071 Uiso 1 1 calc R U . A 1
C44 C 0.3281(2) 0.2150(2) 0.30372(18) 0.0312(6) Uani 1 1 d . . . . .
H44A H 0.3891 0.2487 0.2807 0.037 Uiso 1 1 calc R U . . .
H44B H 0.3206 0.2523 0.3607 0.037 Uiso 1 1 calc R U . . .
C67 C 0.6526(3) 0.1509(3) 0.4350(2) 0.0462(8) Uani 1 1 d . . . . .
H67 H 0.7121 0.1669 0.4777 0.055 Uiso 1 1 calc R U . . .
C9 C 0.7838(2) 0.7538(2) 0.46790(18) 0.0372(7) Uani 1 1 d . . . . .
H9A H 0.8575 0.774 0.4895 0.045 Uiso 1 1 calc R U . . .
H9B H 0.7389 0.7835 0.5112 0.045 Uiso 1 1 calc R U . . .
C57 C 0.0654(2) 0.8583(2) 0.5185(2) 0.0375(7) Uani 1 1 d . . . . .
H57 H 0.029 0.8845 0.5654 0.045 Uiso 1 1 calc R U . . .
C47 C 0.1756(2) 0.1011(2) 0.2382(2) 0.0364(7) Uani 1 1 d . . . . .
H47A H 0.1338 0.0923 0.2861 0.044 Uiso 1 1 calc R U . . .
H47B H 0.1298 0.0795 0.187 0.044 Uiso 1 1 calc R U . . .
C23 C 0.5615(2) 0.3826(2) 0.00023(17) 0.0288(6) Uani 1 1 d . . . . .
H23 H 0.571 0.4379 -0.0255 0.035 Uiso 1 1 calc R U . . .
C39 C 0.2201(2) 0.3788(3) 0.05443(19) 0.0360(7) Uani 1 1 d . . . . .
H39A H 0.2626 0.4044 0.0126 0.043 Uiso 1 1 calc R U . . .
H39B H 0.2582 0.404 0.109 0.043 Uiso 1 1 calc R U . . .
C16 C 0.8108(2) 0.9008(2) 0.25307(19) 0.0323(6) Uani 1 1 d . . . . .
H16A H 0.773 0.9079 0.2023 0.039 Uiso 1 1 calc R U . . .
H16B H 0.772 0.927 0.3018 0.039 Uiso 1 1 calc R U . . .
C27 C 0.4700(2) 0.0909(2) 0.0817(2) 0.0366(7) Uani 1 1 d . . . . .
H27 H 0.4353 0.0259 0.0806 0.044 Uiso 1 1 calc R U . . .
C45 C 0.3428(3) 0.1071(3) 0.3039(2) 0.0445(8) Uani 1 1 d . . . . .
H45A H 0.4161 0.0965 0.2938 0.053 Uiso 1 1 calc R U . . .
H45B H 0.3247 0.0907 0.3577 0.053 Uiso 1 1 calc R U . . .
C26 C 0.4456(2) 0.1390(2) 0.02046(19) 0.0345(7) Uani 1 1 d . . . . .
H26 H 0.3945 0.1084 -0.0229 0.041 Uiso 1 1 calc R U . . .
C59 C 0.1510(3) 0.8767(3) 0.3937(2) 0.0431(8) Uani 1 1 d . . . . .
H59 H 0.172 0.9178 0.3562 0.052 Uiso 1 1 calc R U . . .
C29 C 0.5987(2) 0.2299(2) 0.14879(17) 0.0310(6) Uani 1 1 d . . . . .
H29 H 0.6499 0.2593 0.1923 0.037 Uiso 1 1 calc R U . . .
C60 C 0.1737(2) 0.7804(2) 0.37856(18) 0.0337(6) Uani 1 1 d . . . . .
H60 H 0.2096 0.7552 0.331 0.04 Uiso 1 1 calc R U . . .
C14 C 0.9769(3) 0.8835(2) 0.1963(2) 0.0437(8) Uani 1 1 d . . . . .
H14A H 0.9657 0.8962 0.1403 0.052 Uiso 1 1 calc R U . . .
H14B H 1.053 0.8922 0.2103 0.052 Uiso 1 1 calc R U . . .
C36 C 0.1414(2) 0.5607(2) 0.18415(17) 0.0314(6) Uani 1 1 d . . . . .
H36A H 0.2047 0.5347 0.2007 0.038 Uiso 1 1 calc R U . . .
H36B H 0.1545 0.6342 0.2008 0.038 Uiso 1 1 calc R U . . .
C28 C 0.5450(3) 0.1360(2) 0.14544(19) 0.0380(7) Uani 1 1 d . . . . .
H28 H 0.5594 0.1015 0.1874 0.046 Uiso 1 1 calc R U . . .
C71 C 0.4503(3) 0.7908(3) 0.2220(2) 0.0414(7) Uani 1 1 d . . . . .
H71 H 0.4904 0.7387 0.1917 0.05 Uiso 1 1 calc R U . . .
C46 C 0.2681(3) 0.0430(2) 0.2336(2) 0.0451(8) Uani 1 1 d . . . . .
H46A H 0.3 0.0379 0.1794 0.054 Uiso 1 1 calc R U . . .
H46B H 0.2473 -0.0246 0.2433 0.054 Uiso 1 1 calc R U . . .
C15 C 0.9228(3) 0.9539(2) 0.2603(2) 0.0424(8) Uani 1 1 d . . . . .
H15A H 0.955 0.9617 0.3167 0.051 Uiso 1 1 calc R U . . .
H15B H 0.9256 1.0202 0.2467 0.051 Uiso 1 1 calc R U . . .
C41 C 0.1744(2) 0.2184(2) 0.10523(18) 0.0348(7) Uani 1 1 d . . . . .
H41A H 0.11 0.2434 0.1269 0.042 Uiso 1 1 calc R U . . .
H41B H 0.1584 0.1454 0.0851 0.042 Uiso 1 1 calc R U . . .
C10 C 0.7680(2) 0.7966(2) 0.39177(18) 0.0333(6) Uani 1 1 d . . . . .
H10A H 0.6955 0.7744 0.368 0.04 Uiso 1 1 calc R U . . .
H10B H 0.7782 0.8701 0.408 0.04 Uiso 1 1 calc R U . . .
C40 C 0.2083(3) 0.2659(3) 0.03405(18) 0.0390(7) Uani 1 1 d . . . . .
H40A H 0.1562 0.2405 -0.0131 0.047 Uiso 1 1 calc R U . . .
H40B H 0.276 0.2451 0.0162 0.047 Uiso 1 1 calc R U . . .
Cl1B Cl 0.8919(6) 0.1949(11) -0.0158(5) 0.088(3) Uani 0.294(11) 1 d . . P A 2
Cl2B Cl 0.8162(14) 0.0465(8) 0.0665(9) 0.1503(18) Uani 0.294(11) 1 d . . P A 2
Cl3B Cl 0.8802(10) 0.2356(12) 0.1596(9) 0.085(4) Uani 0.294(11) 1 d . . P A 2
H42 H 0.311(4) 0.215(4) 0.155(3) 0.102 Uiso 1 1 d . U . B 2
H11 H 0.903(4) 0.787(4) 0.348(3) 0.102 Uiso 1 1 d . U . C 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl68 C67 1.758(4) . ?
Cl74 C71 1.750(3) . ?
Cl3A C63 1.757(7) . ?
Cl72 C71 1.755(3) . ?
Cl1A C63 1.729(6) . ?
Cl69 C67 1.753(4) . ?
Cl73 C71 1.764(4) . ?
Cl2A C63 1.772(6) . ?
Cl70 C67 1.737(4) . ?
O49 C48 1.235(3) . ?
O18 C17 1.237(3) . ?
N50 C48 1.346(4) . ?
N50 C51 1.452(3) . ?
N50 H50 0.88 . ?
N55 C56 1.363(4) . ?
N55 C54 1.370(4) . ?
N55 H55 0.88 . ?
N19 C17 1.338(3) . ?
N19 C20 1.461(3) . ?
N19 H19 0.88 . ?
N4 C31 1.345(3) . ?
N4 N3 1.345(3) . ?
N4 C5 1.474(3) . ?
N35 C62 1.346(3) . ?
N35 N34 1.355(3) . ?
N35 C36 1.475(4) . ?
N32 C62 1.317(3) . ?
N32 N33 1.362(3) . ?
N24 C23 1.368(4) . ?
N24 C25 1.373(4) . ?
N24 H24 0.88 . ?
N11 C10 1.463(4) . ?
N11 C12 1.468(3) . ?
N11 H11 0.84(6) . ?
N42 C43 1.470(4) . ?
N42 C41 1.472(4) . ?
N42 H42 0.85(6) . ?
N1 C31 1.328(3) . ?
N1 N2 1.364(3) . ?
N3 N2 1.298(3) . ?
N34 N33 1.289(4) . ?
C22 C23 1.379(4) . ?
C22 C30 1.430(4) . ?
C22 C21 1.497(4) . ?
C6 C7 1.523(4) . ?
C6 C5 1.528(4) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C38 C37 1.515(5) . ?
C38 C39 1.532(4) . ?
C38 H38A 0.99 . ?
C38 H38B 0.99 . ?
C54 C53 1.375(4) . ?
C54 H54 0.95 . ?
C30 C29 1.402(4) . ?
C30 C25 1.419(4) . ?
C53 C61 1.425(4) . ?
C53 C52 1.506(4) . ?
C25 C26 1.393(4) . ?
C56 C57 1.393(4) . ?
C56 C61 1.421(4) . ?
C31 C20 1.501(4) . ?
C52 C51 1.536(4) . ?
C52 H52A 0.99 . ?
C52 H52B 0.99 . ?
C20 C21 1.535(4) . ?
C20 H20 1 . ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?
C62 C51 1.502(3) . ?
C51 H51 1 . ?
C7 C8 1.527(4) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C37 C36 1.524(4) . ?
C37 H37A 0.99 . ?
C37 H37B 0.99 . ?
C43 C48 1.532(4) . ?
C43 C47 1.540(4) . ?
C43 C44 1.562(4) . ?
C8 C9 1.519(5) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C61 C60 1.408(4) . ?
C58 C57 1.368(5) . ?
C58 C59 1.403(5) . ?
C58 H58 0.95 . ?
C17 C12 1.534(4) . ?
C12 C16 1.547(4) . ?
C12 C13 1.564(4) . ?
C13 C14 1.528(4) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C63 Cl2B 1.623(13) . ?
C63 Cl3B 1.724(13) . ?
C63 Cl1B 1.732(10) . ?
C63 H63 1 . ?
C44 C45 1.535(4) . ?
C44 H44A 0.99 . ?
C44 H44B 0.99 . ?
C67 H67 1 . ?
C9 C10 1.522(4) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C57 H57 0.95 . ?
C47 C46 1.520(4) . ?
C47 H47A 0.99 . ?
C47 H47B 0.99 . ?
C23 H23 0.95 . ?
C39 C40 1.519(5) . ?
C39 H39A 0.99 . ?
C39 H39B 0.99 . ?
C16 C15 1.524(4) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C27 C26 1.377(4) . ?
C27 C28 1.397(5) . ?
C27 H27 0.95 . ?
C45 C46 1.535(5) . ?
C45 H45A 0.99 . ?
C45 H45B 0.99 . ?
C26 H26 0.95 . ?
C59 C60 1.379(5) . ?
C59 H59 0.95 . ?
C29 C28 1.383(4) . ?
C29 H29 0.95 . ?
C60 H60 0.95 . ?
C14 C15 1.532(5) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C36 H36A 0.99 . ?
C36 H36B 0.99 . ?
C28 H28 0.95 . ?
C71 H71 1 . ?
C46 H46A 0.99 . ?
C46 H46B 0.99 . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C41 C40 1.515(4) . ?
C41 H41A 0.99 . ?
C41 H41B 0.99 . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C40 H40A 0.99 . ?
C40 H40B 0.99 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C48 N50 C51 120.9(2) . . ?
C48 N50 H50 119.5 . . ?
C51 N50 H50 119.5 . . ?
C56 N55 C54 109.5(2) . . ?
C56 N55 H55 125.3 . . ?
C54 N55 H55 125.3 . . ?
C17 N19 C20 121.6(2) . . ?
C17 N19 H19 119.2 . . ?
C20 N19 H19 119.2 . . ?
C31 N4 N3 108.6(2) . . ?
C31 N4 C5 132.1(2) . . ?
N3 N4 C5 119.3(2) . . ?
C62 N35 N34 107.9(2) . . ?
C62 N35 C36 131.8(2) . . ?
N34 N35 C36 120.1(2) . . ?
C62 N32 N33 105.7(2) . . ?
C23 N24 C25 109.4(2) . . ?
C23 N24 H24 125.3 . . ?
C25 N24 H24 125.3 . . ?
C10 N11 C12 115.7(2) . . ?
C10 N11 H11 110(4) . . ?
C12 N11 H11 109(4) . . ?
C43 N42 C41 115.0(2) . . ?
C43 N42 H42 110(4) . . ?
C41 N42 H42 109(4) . . ?
C31 N1 N2 105.5(2) . . ?
N2 N3 N4 106.5(2) . . ?
N3 N2 N1 111.0(2) . . ?
N33 N34 N35 106.5(2) . . ?
N34 N33 N32 111.1(2) . . ?
C23 C22 C30 105.8(2) . . ?
C23 C22 C21 127.4(3) . . ?
C30 C22 C21 126.8(2) . . ?
C7 C6 C5 114.1(2) . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C37 C38 C39 114.2(3) . . ?
C37 C38 H38A 108.7 . . ?
C39 C38 H38A 108.7 . . ?
C37 C38 H38B 108.7 . . ?
C39 C38 H38B 108.7 . . ?
H38A C38 H38B 107.6 . . ?
N55 C54 C53 109.8(3) . . ?
N55 C54 H54 125.1 . . ?
C53 C54 H54 125.1 . . ?
C29 C30 C25 118.0(3) . . ?
C29 C30 C22 134.3(2) . . ?
C25 C30 C22 107.7(2) . . ?
C54 C53 C61 106.3(2) . . ?
C54 C53 C52 126.2(3) . . ?
C61 C53 C52 127.5(2) . . ?
N24 C25 C26 130.4(3) . . ?
N24 C25 C30 106.9(2) . . ?
C26 C25 C30 122.7(3) . . ?
N55 C56 C57 130.6(3) . . ?
N55 C56 C61 107.2(2) . . ?
C57 C56 C61 122.2(3) . . ?
N1 C31 N4 108.5(2) . . ?
N1 C31 C20 122.7(2) . . ?
N4 C31 C20 128.8(2) . . ?
C53 C52 C51 111.1(2) . . ?
C53 C52 H52A 109.4 . . ?
C51 C52 H52A 109.4 . . ?
C53 C52 H52B 109.4 . . ?
C51 C52 H52B 109.4 . . ?
H52A C52 H52B 108 . . ?
N19 C20 C31 112.1(2) . . ?
N19 C20 C21 113.2(2) . . ?
C31 C20 C21 112.9(2) . . ?
N19 C20 H20 106 . . ?
C31 C20 H20 106 . . ?
C21 C20 H20 106 . . ?
C22 C21 C20 111.2(2) . . ?
C22 C21 H21A 109.4 . . ?
C20 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
C20 C21 H21B 109.4 . . ?
H21A C21 H21B 108 . . ?
N32 C62 N35 108.8(2) . . ?
N32 C62 C51 123.5(2) . . ?
N35 C62 C51 127.7(2) . . ?
N50 C51 C62 112.1(2) . . ?
N50 C51 C52 113.2(2) . . ?
C62 C51 C52 112.4(2) . . ?
N50 C51 H51 106.2 . . ?
C62 C51 H51 106.2 . . ?
C52 C51 H51 106.2 . . ?
C6 C7 C8 114.0(2) . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C38 C37 C36 113.9(2) . . ?
C38 C37 H37A 108.8 . . ?
C36 C37 H37A 108.8 . . ?
C38 C37 H37B 108.8 . . ?
C36 C37 H37B 108.8 . . ?
H37A C37 H37B 107.7 . . ?
N42 C43 C48 107.9(2) . . ?
N42 C43 C47 116.0(2) . . ?
C48 C43 C47 111.8(2) . . ?
N42 C43 C44 108.2(2) . . ?
C48 C43 C44 109.7(2) . . ?
C47 C43 C44 103.1(2) . . ?
C9 C8 C7 113.6(3) . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
N4 C5 C6 111.2(2) . . ?
N4 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
N4 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108 . . ?
C60 C61 C56 118.2(3) . . ?
C60 C61 C53 134.5(3) . . ?
C56 C61 C53 107.2(2) . . ?
C57 C58 C59 121.1(3) . . ?
C57 C58 H58 119.5 . . ?
C59 C58 H58 119.5 . . ?
O49 C48 N50 122.2(2) . . ?
O49 C48 C43 122.3(2) . . ?
N50 C48 C43 115.5(2) . . ?
O18 C17 N19 122.0(2) . . ?
O18 C17 C12 121.7(2) . . ?
N19 C17 C12 116.2(2) . . ?
N11 C12 C17 107.9(2) . . ?
N11 C12 C16 115.5(2) . . ?
C17 C12 C16 111.9(2) . . ?
N11 C12 C13 108.4(2) . . ?
C17 C12 C13 109.5(2) . . ?
C16 C12 C13 103.3(2) . . ?
C14 C13 C12 106.8(2) . . ?
C14 C13 H13A 110.4 . . ?
C12 C13 H13A 110.4 . . ?
C14 C13 H13B 110.4 . . ?
C12 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
Cl2B C63 Cl3B 111.0(8) . . ?
Cl2B C63 Cl1B 112.5(5) . . ?
Cl3B C63 Cl1B 111.1(7) . . ?
Cl1A C63 Cl3A 110.1(3) . . ?
Cl1A C63 Cl2A 111.7(3) . . ?
Cl3A C63 Cl2A 109.5(4) . . ?
Cl1A C63 H63 108.5 . . ?
Cl3A C63 H63 108.5 . . ?
Cl2A C63 H63 108.5 . . ?
C45 C44 C43 106.6(2) . . ?
C45 C44 H44A 110.4 . . ?
C43 C44 H44A 110.4 . . ?
C45 C44 H44B 110.4 . . ?
C43 C44 H44B 110.4 . . ?
H44A C44 H44B 108.6 . . ?
Cl70 C67 Cl69 111.0(2) . . ?
Cl70 C67 Cl68 110.3(2) . . ?
Cl69 C67 Cl68 110.8(2) . . ?
Cl70 C67 H67 108.2 . . ?
Cl69 C67 H67 108.2 . . ?
Cl68 C67 H67 108.2 . . ?
C8 C9 C10 114.7(2) . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C58 C57 C56 118.1(3) . . ?
C58 C57 H57 120.9 . . ?
C56 C57 H57 120.9 . . ?
C46 C47 C43 103.9(2) . . ?
C46 C47 H47A 111 . . ?
C43 C47 H47A 111 . . ?
C46 C47 H47B 111 . . ?
C43 C47 H47B 111 . . ?
H47A C47 H47B 109 . . ?
N24 C23 C22 110.2(3) . . ?
N24 C23 H23 124.9 . . ?
C22 C23 H23 124.9 . . ?
C40 C39 C38 113.0(3) . . ?
C40 C39 H39A 109 . . ?
C38 C39 H39A 109 . . ?
C40 C39 H39B 109 . . ?
C38 C39 H39B 109 . . ?
H39A C39 H39B 107.8 . . ?
C15 C16 C12 103.4(2) . . ?
C15 C16 H16A 111.1 . . ?
C12 C16 H16A 111.1 . . ?
C15 C16 H16B 111.1 . . ?
C12 C16 H16B 111.1 . . ?
H16A C16 H16B 109.1 . . ?
C26 C27 C28 121.2(3) . . ?
C26 C27 H27 119.4 . . ?
C28 C27 H27 119.4 . . ?
C46 C45 C44 105.2(3) . . ?
C46 C45 H45A 110.7 . . ?
C44 C45 H45A 110.7 . . ?
C46 C45 H45B 110.7 . . ?
C44 C45 H45B 110.7 . . ?
H45A C45 H45B 108.8 . . ?
C27 C26 C25 117.6(3) . . ?
C27 C26 H26 121.2 . . ?
C25 C26 H26 121.2 . . ?
C60 C59 C58 121.4(3) . . ?
C60 C59 H59 119.3 . . ?
C58 C59 H59 119.3 . . ?
C28 C29 C30 119.3(3) . . ?
C28 C29 H29 120.4 . . ?
C30 C29 H29 120.4 . . ?
C59 C60 C61 119.0(3) . . ?
C59 C60 H60 120.5 . . ?
C61 C60 H60 120.5 . . ?
C13 C14 C15 105.2(3) . . ?
C13 C14 H14A 110.7 . . ?
C15 C14 H14A 110.7 . . ?
C13 C14 H14B 110.7 . . ?
C15 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
N35 C36 C37 112.5(2) . . ?
N35 C36 H36A 109.1 . . ?
C37 C36 H36A 109.1 . . ?
N35 C36 H36B 109.1 . . ?
C37 C36 H36B 109.1 . . ?
H36A C36 H36B 107.8 . . ?
C29 C28 C27 121.4(3) . . ?
C29 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
Cl74 C71 Cl72 109.57(19) . . ?
Cl74 C71 Cl73 111.23(19) . . ?
Cl72 C71 Cl73 111.20(18) . . ?
Cl74 C71 H71 108.2 . . ?
Cl72 C71 H71 108.2 . . ?
Cl73 C71 H71 108.2 . . ?
C47 C46 C45 102.0(3) . . ?
C47 C46 H46A 111.4 . . ?
C45 C46 H46A 111.4 . . ?
C47 C46 H46B 111.4 . . ?
C45 C46 H46B 111.4 . . ?
H46A C46 H46B 109.2 . . ?
C16 C15 C14 102.5(3) . . ?
C16 C15 H15A 111.3 . . ?
C14 C15 H15A 111.3 . . ?
C16 C15 H15B 111.3 . . ?
C14 C15 H15B 111.3 . . ?
H15A C15 H15B 109.2 . . ?
N42 C41 C40 110.9(3) . . ?
N42 C41 H41A 109.5 . . ?
C40 C41 H41A 109.5 . . ?
N42 C41 H41B 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 108.1 . . ?
N11 C10 C9 111.0(2) . . ?
N11 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
N11 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108 . . ?
C41 C40 C39 114.2(2) . . ?
C41 C40 H40A 108.7 . . ?
C39 C40 H40A 108.7 . . ?
C41 C40 H40B 108.7 . . ?
C39 C40 H40B 108.7 . . ?
H40A C40 H40B 107.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C31 N4 N3 N2 0.2(3) . . . . ?
C5 N4 N3 N2 -179.5(2) . . . . ?
N4 N3 N2 N1 0.0(3) . . . . ?
C31 N1 N2 N3 -0.1(3) . . . . ?
C62 N35 N34 N33 0.2(3) . . . . ?
C36 N35 N34 N33 -174.9(2) . . . . ?
N35 N34 N33 N32 -0.3(3) . . . . ?
C62 N32 N33 N34 0.3(3) . . . . ?
C56 N55 C54 C53 -0.8(3) . . . . ?
C23 C22 C30 C29 -179.8(3) . . . . ?
C21 C22 C30 C29 -3.2(5) . . . . ?
C23 C22 C30 C25 0.5(3) . . . . ?
C21 C22 C30 C25 177.2(2) . . . . ?
N55 C54 C53 C61 0.0(3) . . . . ?
N55 C54 C53 C52 -178.9(2) . . . . ?
C23 N24 C25 C26 -178.0(3) . . . . ?
C23 N24 C25 C30 0.4(3) . . . . ?
C29 C30 C25 N24 179.7(2) . . . . ?
C22 C30 C25 N24 -0.6(3) . . . . ?
C29 C30 C25 C26 -1.8(4) . . . . ?
C22 C30 C25 C26 178.0(3) . . . . ?
C54 N55 C56 C57 -174.9(3) . . . . ?
C54 N55 C56 C61 1.2(3) . . . . ?
N2 N1 C31 N4 0.2(3) . . . . ?
N2 N1 C31 C20 178.1(2) . . . . ?
N3 N4 C31 N1 -0.3(3) . . . . ?
C5 N4 C31 N1 179.3(3) . . . . ?
N3 N4 C31 C20 -178.0(2) . . . . ?
C5 N4 C31 C20 1.6(5) . . . . ?
C54 C53 C52 C51 64.6(3) . . . . ?
C61 C53 C52 C51 -114.2(3) . . . . ?
C17 N19 C20 C31 -100.8(3) . . . . ?
C17 N19 C20 C21 130.2(3) . . . . ?
N1 C31 C20 N19 115.8(3) . . . . ?
N4 C31 C20 N19 -66.8(3) . . . . ?
N1 C31 C20 C21 -115.0(3) . . . . ?
N4 C31 C20 C21 62.4(3) . . . . ?
C23 C22 C21 C20 63.7(3) . . . . ?
C30 C22 C21 C20 -112.2(3) . . . . ?
N19 C20 C21 C22 -178.4(2) . . . . ?
C31 C20 C21 C22 53.0(3) . . . . ?
N33 N32 C62 N35 -0.2(3) . . . . ?
N33 N32 C62 C51 178.5(2) . . . . ?
N34 N35 C62 N32 0.0(3) . . . . ?
C36 N35 C62 N32 174.3(3) . . . . ?
N34 N35 C62 C51 -178.6(2) . . . . ?
C36 N35 C62 C51 -4.3(5) . . . . ?
C48 N50 C51 C62 -91.5(3) . . . . ?
C48 N50 C51 C52 140.2(2) . . . . ?
N32 C62 C51 N50 116.7(3) . . . . ?
N35 C62 C51 N50 -64.9(3) . . . . ?
N32 C62 C51 C52 -114.5(3) . . . . ?
N35 C62 C51 C52 63.9(3) . . . . ?
C53 C52 C51 N50 -173.4(2) . . . . ?
C53 C52 C51 C62 58.4(3) . . . . ?
C5 C6 C7 C8 -77.6(3) . . . . ?
C39 C38 C37 C36 -75.2(3) . . . . ?
C41 N42 C43 C48 -75.3(3) . . . . ?
C41 N42 C43 C47 51.0(3) . . . . ?
C41 N42 C43 C44 166.2(2) . . . . ?
C6 C7 C8 C9 172.0(2) . . . . ?
C31 N4 C5 C6 131.4(3) . . . . ?
N3 N4 C5 C6 -49.0(3) . . . . ?
C7 C6 C5 N4 -65.9(3) . . . . ?
N55 C56 C61 C60 -178.2(2) . . . . ?
C57 C56 C61 C60 -1.6(4) . . . . ?
N55 C56 C61 C53 -1.2(3) . . . . ?
C57 C56 C61 C53 175.4(3) . . . . ?
C54 C53 C61 C60 177.0(3) . . . . ?
C52 C53 C61 C60 -4.1(5) . . . . ?
C54 C53 C61 C56 0.7(3) . . . . ?
C52 C53 C61 C56 179.7(2) . . . . ?
C51 N50 C48 O49 5.0(4) . . . . ?
C51 N50 C48 C43 -171.8(2) . . . . ?
N42 C43 C48 O49 142.0(3) . . . . ?
C47 C43 C48 O49 13.4(4) . . . . ?
C44 C43 C48 O49 -100.4(3) . . . . ?
N42 C43 C48 N50 -41.2(3) . . . . ?
C47 C43 C48 N50 -169.9(2) . . . . ?
C44 C43 C48 N50 76.4(3) . . . . ?
C20 N19 C17 O18 4.1(4) . . . . ?
C20 N19 C17 C12 -172.3(2) . . . . ?
C10 N11 C12 C17 -77.3(3) . . . . ?
C10 N11 C12 C16 48.7(3) . . . . ?
C10 N11 C12 C13 164.1(2) . . . . ?
O18 C17 C12 N11 147.4(3) . . . . ?
N19 C17 C12 N11 -36.2(3) . . . . ?
O18 C17 C12 C16 19.2(4) . . . . ?
N19 C17 C12 C16 -164.4(2) . . . . ?
O18 C17 C12 C13 -94.8(3) . . . . ?
N19 C17 C12 C13 81.6(3) . . . . ?
N11 C12 C13 C14 -110.6(3) . . . . ?
C17 C12 C13 C14 131.9(3) . . . . ?
C16 C12 C13 C14 12.5(3) . . . . ?
N42 C43 C44 C45 -110.1(3) . . . . ?
C48 C43 C44 C45 132.4(2) . . . . ?
C47 C43 C44 C45 13.2(3) . . . . ?
C7 C8 C9 C10 -75.8(3) . . . . ?
C59 C58 C57 C56 0.3(5) . . . . ?
N55 C56 C57 C58 176.4(3) . . . . ?
C61 C56 C57 C58 0.8(4) . . . . ?
N42 C43 C47 C46 82.4(3) . . . . ?
C48 C43 C47 C46 -153.4(2) . . . . ?
C44 C43 C47 C46 -35.7(3) . . . . ?
C25 N24 C23 C22 -0.1(3) . . . . ?
C30 C22 C23 N24 -0.3(3) . . . . ?
C21 C22 C23 N24 -176.9(2) . . . . ?
C37 C38 C39 C40 170.3(2) . . . . ?
N11 C12 C16 C15 83.6(3) . . . . ?
C17 C12 C16 C15 -152.5(2) . . . . ?
C13 C12 C16 C15 -34.7(3) . . . . ?
C43 C44 C45 C46 13.7(3) . . . . ?
C28 C27 C26 C25 0.1(4) . . . . ?
N24 C25 C26 C27 179.5(3) . . . . ?
C30 C25 C26 C27 1.3(4) . . . . ?
C57 C58 C59 C60 -0.5(5) . . . . ?
C25 C30 C29 C28 0.8(4) . . . . ?
C22 C30 C29 C28 -178.9(3) . . . . ?
C58 C59 C60 C61 -0.4(5) . . . . ?
C56 C61 C60 C59 1.4(4) . . . . ?
C53 C61 C60 C59 -174.6(3) . . . . ?
C12 C13 C14 C15 14.2(3) . . . . ?
C62 N35 C36 C37 137.7(3) . . . . ?
N34 N35 C36 C37 -48.5(3) . . . . ?
C38 C37 C36 N35 -65.9(3) . . . . ?
C30 C29 C28 C27 0.5(4) . . . . ?
C26 C27 C28 C29 -1.0(5) . . . . ?
C43 C47 C46 C45 44.5(3) . . . . ?
C44 C45 C46 C47 -35.6(3) . . . . ?
C12 C16 C15 C14 43.9(3) . . . . ?
C13 C14 C15 C16 -35.9(3) . . . . ?
C43 N42 C41 C40 172.1(2) . . . . ?
C12 N11 C10 C9 172.7(2) . . . . ?
C8 C9 C10 N11 -65.2(3) . . . . ?
N42 C41 C40 C39 -67.4(3) . . . . ?
C38 C39 C40 C41 -76.4(3) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ea720f5
_database_code_depnum_ccdc_archive 'CCDC 1844784'
loop_
_audit_author_name
_audit_author_address
'Justyna Kalinowska-Tluscik'
;Jagiellonian University
Poland
;
_audit_update_record             
;
2018-05-22 deposited with the CCDC.	2020-01-07 downloaded from the CCDC.
;

_audit_creation_date             2018-02-22T12:00:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C56 H54 F6 N12 O2'
_chemical_formula_moiety         'C28 H27 F3 N6 O'
_chemical_formula_weight         1041.11

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.8092(4)
_cell_length_b                   14.1679(6)
_cell_length_c                   17.2034(7)
_cell_angle_alpha                78.408(4)
_cell_angle_beta                 86.646(3)
_cell_angle_gamma                86.284(3)
_cell_volume                     2572.64(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    5830
_cell_measurement_theta_min      3.693
_cell_measurement_theta_max      70.977

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             1088

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.69465
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.731
_shelx_estimated_absorpt_T_max   0.921

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_ambient_temperature      130(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0471955
_diffrn_orient_matrix_ub_12      -0.0071803
_diffrn_orient_matrix_ub_13      -0.0849734
_diffrn_orient_matrix_ub_21      -0.0143434
_diffrn_orient_matrix_ub_22      -0.1098237
_diffrn_orient_matrix_ub_23      0.0199737
_diffrn_orient_matrix_ub_31      -0.1341999
_diffrn_orient_matrix_ub_32      0.015638
_diffrn_orient_matrix_ub_33      -0.0274818
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_number            16985
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.189
_diffrn_reflns_theta_max         71.298
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_reflns_Friedel_coverage         0
_reflns_number_total             9771
_reflns_number_gt                7341
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0912P)²+0.6829P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         9771
_refine_ls_number_parameters     739
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1705
_refine_ls_wR_factor_gt          0.1514
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.199
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.052

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F73 F 0.44653(14) 0.18129(12) 0.73085(10) 0.0561(4) Uani 1 1 d . . . . .
F33 F -0.39584(14) 1.21206(12) 0.87107(11) 0.0593(4) Uani 1 1 d . . . . .
F32 F -0.27192(16) 1.04877(12) 0.94226(10) 0.0620(5) Uani 1 1 d . . . . .
F34 F -0.31261(15) 1.30768(11) 0.72694(11) 0.0579(4) Uani 1 1 d . . . . .
N1 N 0.15402(16) 0.77884(13) 0.81851(11) 0.0311(4) Uani 1 1 d . . . . .
N42 N -0.10485(17) 0.77207(14) 0.61890(12) 0.0362(4) Uani 1 1 d . . . . .
N41 N -0.09968(16) 0.67438(13) 0.63933(11) 0.0324(4) Uani 1 1 d . . . . .
N44 N -0.11933(16) 0.72845(14) 0.74836(11) 0.0348(4) Uani 1 1 d . . . . .
N3 N 0.17006(16) 0.66327(14) 0.75632(12) 0.0356(4) Uani 1 1 d . . . . .
N68 N -0.00122(16) 0.49297(13) 0.74588(11) 0.0302(4) Uani 1 1 d . . . . .
N43 N -0.11561(16) 0.80335(14) 0.68464(11) 0.0349(4) Uani 1 1 d . . . . .
N9 N -0.06844(17) 0.79208(14) 0.90733(12) 0.0358(4) Uani 1 1 d . . . . .
F72 F 0.37370(14) 0.33345(14) 0.61979(9) 0.0608(5) Uani 1 1 d . . . . .
N2 N 0.15957(17) 0.68144(13) 0.82713(12) 0.0346(4) Uani 1 1 d . . . . .
N49 N 0.12363(18) 0.66001(15) 0.55291(12) 0.0370(4) Uani 1 1 d . . . . .
O8 O 0.03515(17) 0.81950(16) 1.01025(12) 0.0577(5) Uani 1 1 d . . . . .
F74 F 0.30407(17) 0.12933(13) 0.86516(11) 0.0698(5) Uani 1 1 d . . . . .
O48 O 0.02475(18) 0.61517(18) 0.45540(12) 0.0634(6) Uani 1 1 d . . . . .
N4 N 0.17226(17) 0.74711(15) 0.70073(12) 0.0395(5) Uani 1 1 d . . . . .
C45 C -0.11000(19) 0.64918(16) 0.71866(13) 0.0331(5) Uani 1 1 d . . . . .
C18 C 0.3863(2) 0.82133(17) 0.88797(14) 0.0350(5) Uani 1 1 d . . . . .
N28 N 0.04682(17) 0.96688(13) 0.73990(11) 0.0315(4) Uani 1 1 d . . . . .
C10 C -0.1897(2) 0.79595(17) 0.94837(15) 0.0385(5) Uani 1 1 d . . . . .
H10A H -0.2524 0.8198 0.9083 0.046 Uiso 1 1 calc R U . . .
H10B H -0.1893 0.8436 0.9833 0.046 Uiso 1 1 calc R U . . .
C71 C 0.1923(2) 0.36346(18) 0.69739(15) 0.0401(5) Uani 1 1 d . . . . .
H71 H 0.1674 0.4175 0.6581 0.048 Uiso 1 1 calc R U . . .
C11 C -0.2294(2) 0.70162(17) 0.99787(14) 0.0349(5) Uani 1 1 d . . . . .
C51 C 0.2447(2) 0.78906(17) 0.46894(13) 0.0357(5) Uani 1 1 d . . . . .
C73 C 0.3394(2) 0.23197(18) 0.74269(15) 0.0405(5) Uani 1 1 d . . . . .
C70 C 0.1197(2) 0.33664(16) 0.76703(14) 0.0351(5) Uani 1 1 d . . . . .
C6 C 0.1546(2) 0.82133(17) 0.88948(14) 0.0354(5) Uani 1 1 d . . . . .
H6 H 0.1613 0.8924 0.8703 0.042 Uiso 1 1 calc R U . . .
C33 C -0.2933(2) 1.17876(18) 0.83516(16) 0.0429(6) Uani 1 1 d . . . . .
C56 C 0.3547(2) 0.81933(19) 0.42829(16) 0.0446(6) Uani 1 1 d . . . . .
H56 H 0.422 0.7737 0.4245 0.054 Uiso 1 1 calc R U . . .
C74 C 0.2660(2) 0.20635(18) 0.81022(16) 0.0431(6) Uani 1 1 d . . . . .
C47 C 0.0246(2) 0.63138(18) 0.52294(14) 0.0393(5) Uani 1 1 d . . . . .
C34 C -0.2496(2) 1.22584(17) 0.76176(16) 0.0410(5) Uani 1 1 d . . . . .
C72 C 0.3010(2) 0.3102(2) 0.68655(14) 0.0412(5) Uani 1 1 d . . . . .
C30 C -0.0810(2) 1.10883(16) 0.76077(14) 0.0340(5) Uani 1 1 d . . . . .
C50 C 0.2362(2) 0.68335(17) 0.50469(14) 0.0387(5) Uani 1 1 d . . . . .
H50A H 0.2416 0.6466 0.4612 0.046 Uiso 1 1 calc R U . . .
H50B H 0.3085 0.6618 0.5379 0.046 Uiso 1 1 calc R U . . .
C12 C -0.1480(2) 0.62136(17) 1.01710(14) 0.0382(5) Uani 1 1 d . . . . .
H12 H -0.064 0.6244 0.9975 0.046 Uiso 1 1 calc R U . . .
C32 C -0.2290(2) 1.09620(18) 0.87027(15) 0.0437(6) Uani 1 1 d . . . . .
C75 C 0.1557(2) 0.25674(17) 0.82330(15) 0.0395(5) Uani 1 1 d . . . . .
H75 H 0.1054 0.2369 0.8702 0.047 Uiso 1 1 calc R U . . .
C7 C 0.0341(2) 0.80833(17) 0.94169(14) 0.0382(5) Uani 1 1 d . . . . .
C5 C 0.1626(2) 0.81757(17) 0.74071(14) 0.0366(5) Uani 1 1 d . . . . .
C52 C 0.1466(2) 0.85684(18) 0.47271(14) 0.0386(5) Uani 1 1 d . . . . .
H52 H 0.0703 0.837 0.4992 0.046 Uiso 1 1 calc R U . . .
C69 C -0.0009(2) 0.39044(17) 0.78253(16) 0.0420(6) Uani 1 1 d . . . . .
H69A H -0.0692 0.3609 0.7617 0.05 Uiso 1 1 calc R U . . .
H69B H -0.0167 0.3838 0.8406 0.05 Uiso 1 1 calc R U . . .
C35 C -0.1445(2) 1.19284(16) 0.72411(15) 0.0373(5) Uani 1 1 d . . . . .
H35 H -0.1158 1.2271 0.6737 0.045 Uiso 1 1 calc R U . . .
C17 C 0.2705(2) 0.78498(17) 0.93547(14) 0.0381(5) Uani 1 1 d . . . . .
H17A H 0.2649 0.8074 0.9865 0.046 Uiso 1 1 calc R U . . .
H17B H 0.2756 0.7135 0.9474 0.046 Uiso 1 1 calc R U . . .
C53 C 0.1595(2) 0.95323(19) 0.43795(16) 0.0478(6) Uani 1 1 d . . . . .
H53 H 0.0925 0.9992 0.4415 0.057 Uiso 1 1 calc R U . . .
C29 C 0.0348(2) 1.07226(16) 0.72054(15) 0.0375(5) Uani 1 1 d . . . . .
H29A H 0.0312 1.0942 0.6623 0.045 Uiso 1 1 calc R U . . .
H29B H 0.1083 1.0991 0.738 0.045 Uiso 1 1 calc R U . . .
C46 C -0.0931(2) 0.61580(18) 0.57761(14) 0.0371(5) Uani 1 1 d . . . . .
H46 H -0.0905 0.5464 0.6049 0.044 Uiso 1 1 calc R U . . .
C23 C 0.4579(2) 0.76573(19) 0.84299(17) 0.0446(6) Uani 1 1 d . . . . .
H23 H 0.4365 0.7017 0.8434 0.054 Uiso 1 1 calc R U . . .
C27 C 0.2863(3) 1.04283(19) 0.60798(19) 0.0542(7) Uani 1 1 d . . . . .
H27A H 0.278 1.0828 0.5541 0.065 Uiso 1 1 calc R U . A 1
H27B H 0.2979 1.0795 0.6501 0.065 Uiso 1 1 calc R U . A 1
C19 C 0.4185(2) 0.91524(17) 0.88622(15) 0.0405(5) Uani 1 1 d . . . . .
H19 H 0.3708 0.9541 0.9172 0.049 Uiso 1 1 calc R U . . .
C61 C -0.5460(2) 0.5893(2) 0.67492(18) 0.0544(7) Uani 1 1 d . . . . .
H61 H -0.6204 0.5788 0.7069 0.065 Uiso 1 1 calc R U . . .
C58 C -0.3283(2) 0.62025(18) 0.57957(14) 0.0394(5) Uani 1 1 d . . . . .
C31 C -0.1240(2) 1.05995(17) 0.83484(15) 0.0401(5) Uani 1 1 d . . . . .
H31 H -0.0815 1.0024 0.8606 0.048 Uiso 1 1 calc R U . . .
C22 C 0.5602(2) 0.8020(2) 0.79749(18) 0.0531(7) Uani 1 1 d . . . . .
H22 H 0.6094 0.7627 0.7676 0.064 Uiso 1 1 calc R U . . .
C20 C 0.5198(2) 0.95239(19) 0.83946(17) 0.0488(6) Uani 1 1 d . . . . .
H20 H 0.5401 1.017 0.8377 0.059 Uiso 1 1 calc R U . . .
C66 C -0.2550(3) 0.4512(2) 0.87490(19) 0.0571(8) Uani 1 1 d . . . . .
H66A H -0.3081 0.3958 0.8795 0.069 Uiso 1 1 calc R U . B 3
H66B H -0.1904 0.4422 0.9146 0.069 Uiso 1 1 calc DR U . B 3
C63 C -0.4053(2) 0.6968(2) 0.59607(17) 0.0475(6) Uani 1 1 d . . . . .
H63 H -0.3832 0.7609 0.5747 0.057 Uiso 1 1 calc R U . . .
C16 C -0.3519(2) 0.69599(19) 1.02744(16) 0.0449(6) Uani 1 1 d . . . . .
H16 H -0.4084 0.7504 1.0148 0.054 Uiso 1 1 calc R U . . .
C67 C -0.3164(2) 0.5525(2) 0.8505(2) 0.0592(8) Uani 1 1 d . . . . .
H67A H -0.2881 0.6042 0.8752 0.071 Uiso 1 1 calc DR U . C 3
H67B H -0.4059 0.5577 0.84 0.071 Uiso 1 1 calc R U . C 3
C21 C 0.5909(2) 0.8961(2) 0.79567(17) 0.0516(7) Uani 1 1 d . . . . .
H21 H 0.6608 0.9215 0.7642 0.062 Uiso 1 1 calc R U . . .
C59 C -0.3629(2) 0.5275(2) 0.61291(18) 0.0514(7) Uani 1 1 d . . . . .
H59 H -0.312 0.4736 0.6029 0.062 Uiso 1 1 calc R U . . .
C57 C -0.2101(2) 0.6355(2) 0.52901(15) 0.0454(6) Uani 1 1 d . . . . .
H57A H -0.2118 0.7029 0.4989 0.054 Uiso 1 1 calc R U . . .
H57B H -0.2059 0.5924 0.4901 0.054 Uiso 1 1 calc R U . . .
C62 C -0.5131(2) 0.6817(2) 0.64274(18) 0.0531(7) Uani 1 1 d . . . . .
H62 H -0.5647 0.7352 0.6527 0.064 Uiso 1 1 calc R U . . .
C26 C 0.3529(2) 0.94384(19) 0.61487(19) 0.0531(7) Uani 1 1 d . . . . .
H26A H 0.4046 0.9204 0.6612 0.064 Uiso 1 1 calc DR U . D 1
H26B H 0.3847 0.9237 0.5652 0.064 Uiso 1 1 calc R U . D 1
C55 C 0.3668(3) 0.9155(2) 0.3933(2) 0.0587(8) Uani 1 1 d . . . . .
H55 H 0.4424 0.9355 0.3658 0.07 Uiso 1 1 calc R U . . .
C13 C -0.1881(2) 0.53692(19) 1.06466(17) 0.0500(6) Uani 1 1 d . . . . .
H13 H -0.1316 0.4825 1.0774 0.06 Uiso 1 1 calc R U . . .
C15 C -0.3922(3) 0.6113(2) 1.0753(2) 0.0603(8) Uani 1 1 d . . . . .
H15 H -0.4759 0.6081 1.0954 0.072 Uiso 1 1 calc R U . . .
C54 C 0.2694(3) 0.9823(2) 0.39833(19) 0.0564(7) Uani 1 1 d . . . . .
H54 H 0.278 1.0482 0.3745 0.068 Uiso 1 1 calc R U . . .
C60 C -0.4703(3) 0.5124(2) 0.6604(2) 0.0606(8) Uani 1 1 d . . . . .
H60 H -0.4919 0.4485 0.6831 0.073 Uiso 1 1 calc R U . . .
C14 C -0.3097(3) 0.5314(2) 1.0936(2) 0.0606(8) Uani 1 1 d . . . . .
H14 H -0.337 0.4733 1.1259 0.073 Uiso 1 1 calc R U . . .
C24A C 0.1707(5) 0.9284(4) 0.7165(4) 0.0273(12) Uani 0.553(7) 1 d . . P E 1
H24A H 0.2343 0.9495 0.7484 0.033 Uiso 0.553(7) 1 calc R U P E 1
C25A C 0.2105(4) 0.9527(3) 0.6302(2) 0.0368(12) Uani 0.553(7) 1 d . . P E 1
H25A H 0.1555 0.9375 0.5902 0.044 Uiso 0.553(7) 1 calc R U P E 1
C24B C 0.1400(7) 0.9173(5) 0.6925(4) 0.0275(15) Uani 0.447(7) 1 d . . P E 2
H24B H 0.1127 0.9171 0.638 0.033 Uiso 0.447(7) 1 calc R U P E 2
C25B C 0.2610(4) 0.9663(3) 0.6913(3) 0.0318(14) Uani 0.447(7) 1 d . . P E 2
H25B H 0.2967 0.9748 0.7416 0.038 Uiso 0.447(7) 1 calc DR U P E 2
C64A C -0.0964(12) 0.5536(9) 0.7792(6) 0.034(2) Uani 0.398(7) 1 d . . P F 3
H64A H -0.0726 0.5649 0.8318 0.041 Uiso 0.398(7) 1 calc R U P F 3
C65A C -0.2196(5) 0.5103(4) 0.7862(4) 0.0371(17) Uani 0.398(7) 1 d . . P F 3
H65A H -0.2525 0.4907 0.739 0.045 Uiso 0.398(7) 1 calc R U P F 3
C64B C -0.1224(6) 0.5438(5) 0.7577(4) 0.0250(12) Uani 0.602(7) 1 d . . P F 4
H64B H -0.1864 0.5164 0.7302 0.03 Uiso 0.602(7) 1 calc R U P F 4
C65B C -0.1668(3) 0.5411(2) 0.8424(2) 0.0310(10) Uani 0.602(7) 1 d . . P F 4
H65B H -0.1148 0.5655 0.8795 0.037 Uiso 0.602(7) 1 calc DR U P F 4
H28 H -0.017(2) 0.9447(18) 0.7239(15) 0.031(6) Uiso 1 1 d . . . . .
H9 H -0.068(2) 0.7790(18) 0.8645(16) 0.028(6) Uiso 1 1 d . . . . .
H49 H 0.117(3) 0.677(2) 0.5983(18) 0.048(8) Uiso 1 1 d . . . . .
H68 H 0.063(3) 0.519(2) 0.7614(16) 0.043(7) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F73 C73 1.349(3) . ?
F33 C33 1.342(3) . ?
F32 C32 1.356(3) . ?
F34 C34 1.354(3) . ?
N1 C5 1.341(3) . ?
N1 N2 1.356(2) . ?
N1 C6 1.466(3) . ?
N42 N43 1.292(3) . ?
N42 N41 1.356(3) . ?
N41 C45 1.339(3) . ?
N41 C46 1.469(3) . ?
N44 C45 1.320(3) . ?
N44 N43 1.365(3) . ?
N3 N2 1.292(3) . ?
N3 N4 1.368(3) . ?
N68 C69 1.463(3) . ?
N68 C64A 1.463(12) . ?
N68 C64B 1.476(7) . ?
N68 H68 0.89(3) . ?
N9 C7 1.340(3) . ?
N9 C10 1.455(3) . ?
N9 H9 0.79(3) . ?
F72 C72 1.350(3) . ?
N49 C47 1.335(3) . ?
N49 C50 1.450(3) . ?
N49 H49 0.86(3) . ?
O8 C7 1.222(3) . ?
F74 C74 1.351(3) . ?
O48 C47 1.229(3) . ?
N4 C5 1.317(3) . ?
C45 C64B 1.520(8) . ?
C45 C64A 1.539(12) . ?
C18 C23 1.384(3) . ?
C18 C19 1.391(3) . ?
C18 C17 1.515(3) . ?
N28 C29 1.462(3) . ?
N28 C24A 1.477(6) . ?
N28 C24B 1.488(7) . ?
N28 H28 0.86(2) . ?
C10 C11 1.507(3) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C71 C72 1.378(3) . ?
C71 C70 1.393(3) . ?
C71 H71 0.95 . ?
C11 C12 1.390(3) . ?
C11 C16 1.391(3) . ?
C51 C56 1.391(3) . ?
C51 C52 1.391(3) . ?
C51 C50 1.507(3) . ?
C73 C74 1.368(4) . ?
C73 C72 1.375(4) . ?
C70 C75 1.384(3) . ?
C70 C69 1.505(3) . ?
C6 C17 1.527(3) . ?
C6 C7 1.537(3) . ?
C6 H6 1 . ?
C33 C32 1.370(4) . ?
C33 C34 1.377(4) . ?
C56 C55 1.386(4) . ?
C56 H56 0.95 . ?
C74 C75 1.379(3) . ?
C47 C46 1.537(3) . ?
C34 C35 1.377(3) . ?
C30 C35 1.389(3) . ?
C30 C31 1.392(3) . ?
C30 C29 1.507(3) . ?
C50 H50A 0.99 . ?
C50 H50B 0.99 . ?
C12 C13 1.386(3) . ?
C12 H12 0.95 . ?
C32 C31 1.376(3) . ?
C75 H75 0.95 . ?
C5 C24B 1.501(7) . ?
C5 C24A 1.549(6) . ?
C52 C53 1.389(4) . ?
C52 H52 0.95 . ?
C69 H69A 0.99 . ?
C69 H69B 0.99 . ?
C35 H35 0.95 . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C53 C54 1.379(4) . ?
C53 H53 0.95 . ?
C29 H29A 0.99 . ?
C29 H29B 0.99 . ?
C46 C57 1.537(3) . ?
C46 H46 1 . ?
C23 C22 1.382(4) . ?
C23 H23 0.95 . ?
C27 C26 1.521(4) . ?
C27 C25A 1.532(5) . ?
C27 C25B 1.634(5) . ?
C27 H27A 0.99 . ?
C27 H27B 0.99 . ?
C19 C20 1.387(4) . ?
C19 H19 0.95 . ?
C61 C60 1.375(4) . ?
C61 C62 1.375(4) . ?
C61 H61 0.95 . ?
C58 C63 1.388(3) . ?
C58 C59 1.390(4) . ?
C58 C57 1.505(3) . ?
C31 H31 0.95 . ?
C22 C21 1.388(4) . ?
C22 H22 0.95 . ?
C20 C21 1.374(4) . ?
C20 H20 0.95 . ?
C66 C67 1.531(4) . ?
C66 C65A 1.624(6) . ?
C66 C65B 1.629(4) . ?
C66 H66A 0.99 . ?
C66 H66B 0.99 . ?
C63 C62 1.379(4) . ?
C63 H63 0.95 . ?
C16 C15 1.391(4) . ?
C16 H16 0.95 . ?
C67 C65B 1.615(4) . ?
C67 C65A 1.651(6) . ?
C67 H67A 0.99 . ?
C67 H67B 0.99 . ?
C21 H21 0.95 . ?
C59 C60 1.382(4) . ?
C59 H59 0.95 . ?
C57 H57A 0.99 . ?
C57 H57B 0.99 . ?
C62 H62 0.95 . ?
C26 C25A 1.548(5) . ?
C26 C25B 1.670(5) . ?
C26 H26A 0.99 . ?
C26 H26B 0.99 . ?
C55 C54 1.381(4) . ?
C55 H55 0.95 . ?
C13 C14 1.379(4) . ?
C13 H13 0.95 . ?
C15 C14 1.391(4) . ?
C15 H15 0.95 . ?
C54 H54 0.95 . ?
C60 H60 0.95 . ?
C14 H14 0.95 . ?
C24A C25A 1.499(7) . ?
C24A H24A 1 . ?
C25A H25A 1 . ?
C24B C25B 1.517(9) . ?
C24B H24B 1 . ?
C25B H25B 1 . ?
C64A C65A 1.490(13) . ?
C64A H64A 1 . ?
C65A H65A 1 . ?
C64B C65B 1.501(7) . ?
C64B H64B 1 . ?
C65B H65B 1 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 N2 108.36(19) . . ?
C5 N1 C6 132.19(19) . . ?
N2 N1 C6 119.00(18) . . ?
N43 N42 N41 106.32(18) . . ?
C45 N41 N42 108.42(18) . . ?
C45 N41 C46 131.2(2) . . ?
N42 N41 C46 120.28(19) . . ?
C45 N44 N43 105.88(19) . . ?
N2 N3 N4 110.57(18) . . ?
C69 N68 C64A 114.5(5) . . ?
C69 N68 C64B 112.2(3) . . ?
C69 N68 H68 110.0(17) . . ?
C64A N68 H68 95.6(19) . . ?
C64B N68 H68 114.4(18) . . ?
N42 N43 N44 110.85(18) . . ?
C7 N9 C10 120.8(2) . . ?
C7 N9 H9 123.5(18) . . ?
C10 N9 H9 115.7(18) . . ?
N3 N2 N1 106.48(18) . . ?
C47 N49 C50 121.7(2) . . ?
C47 N49 H49 119.9(19) . . ?
C50 N49 H49 117.0(19) . . ?
C5 N4 N3 106.05(19) . . ?
N44 C45 N41 108.5(2) . . ?
N44 C45 C64B 131.5(3) . . ?
N41 C45 C64B 119.6(3) . . ?
N44 C45 C64A 116.0(4) . . ?
N41 C45 C64A 134.9(4) . . ?
C23 C18 C19 118.8(2) . . ?
C23 C18 C17 122.1(2) . . ?
C19 C18 C17 119.1(2) . . ?
C29 N28 C24A 112.5(3) . . ?
C29 N28 C24B 117.8(3) . . ?
C29 N28 H28 108.5(17) . . ?
C24A N28 H28 118.0(17) . . ?
C24B N28 H28 96.0(17) . . ?
N9 C10 C11 115.39(19) . . ?
N9 C10 H10A 108.4 . . ?
C11 C10 H10A 108.4 . . ?
N9 C10 H10B 108.4 . . ?
C11 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C72 C71 C70 118.8(2) . . ?
C72 C71 H71 120.6 . . ?
C70 C71 H71 120.6 . . ?
C12 C11 C16 118.9(2) . . ?
C12 C11 C10 122.7(2) . . ?
C16 C11 C10 118.4(2) . . ?
C56 C51 C52 118.8(2) . . ?
C56 C51 C50 118.2(2) . . ?
C52 C51 C50 123.0(2) . . ?
F73 C73 C74 121.0(2) . . ?
F73 C73 C72 120.6(2) . . ?
C74 C73 C72 118.4(2) . . ?
C75 C70 C71 120.1(2) . . ?
C75 C70 C69 118.0(2) . . ?
C71 C70 C69 121.8(2) . . ?
N1 C6 C17 110.15(19) . . ?
N1 C6 C7 113.48(18) . . ?
C17 C6 C7 112.9(2) . . ?
N1 C6 H6 106.6 . . ?
C17 C6 H6 106.6 . . ?
C7 C6 H6 106.6 . . ?
F33 C33 C32 121.0(2) . . ?
F33 C33 C34 121.3(2) . . ?
C32 C33 C34 117.7(2) . . ?
C55 C56 C51 120.5(2) . . ?
C55 C56 H56 119.7 . . ?
C51 C56 H56 119.7 . . ?
F74 C74 C73 118.2(2) . . ?
F74 C74 C75 119.9(2) . . ?
C73 C74 C75 121.9(2) . . ?
O48 C47 N49 123.2(2) . . ?
O48 C47 C46 119.5(2) . . ?
N49 C47 C46 117.3(2) . . ?
F34 C34 C33 117.9(2) . . ?
F34 C34 C35 119.9(2) . . ?
C33 C34 C35 122.1(2) . . ?
F72 C72 C73 117.6(2) . . ?
F72 C72 C71 120.7(2) . . ?
C73 C72 C71 121.7(2) . . ?
C35 C30 C31 119.6(2) . . ?
C35 C30 C29 119.7(2) . . ?
C31 C30 C29 120.7(2) . . ?
N49 C50 C51 114.28(19) . . ?
N49 C50 H50A 108.7 . . ?
C51 C50 H50A 108.7 . . ?
N49 C50 H50B 108.7 . . ?
C51 C50 H50B 108.7 . . ?
H50A C50 H50B 107.6 . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
F32 C32 C33 118.2(2) . . ?
F32 C32 C31 119.4(2) . . ?
C33 C32 C31 122.4(2) . . ?
C74 C75 C70 118.9(2) . . ?
C74 C75 H75 120.5 . . ?
C70 C75 H75 120.5 . . ?
O8 C7 N9 123.6(2) . . ?
O8 C7 C6 118.6(2) . . ?
N9 C7 C6 117.6(2) . . ?
N4 C5 N1 108.5(2) . . ?
N4 C5 C24B 115.9(3) . . ?
N1 C5 C24B 134.3(3) . . ?
N4 C5 C24A 133.6(3) . . ?
N1 C5 C24A 117.6(3) . . ?
C53 C52 C51 120.5(2) . . ?
C53 C52 H52 119.8 . . ?
C51 C52 H52 119.8 . . ?
N68 C69 C70 112.72(19) . . ?
N68 C69 H69A 109 . . ?
C70 C69 H69A 109 . . ?
N68 C69 H69B 109 . . ?
C70 C69 H69B 109 . . ?
H69A C69 H69B 107.8 . . ?
C34 C35 C30 119.1(2) . . ?
C34 C35 H35 120.4 . . ?
C30 C35 H35 120.4 . . ?
C18 C17 C6 110.81(19) . . ?
C18 C17 H17A 109.5 . . ?
C6 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C6 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C54 C53 C52 120.1(2) . . ?
C54 C53 H53 119.9 . . ?
C52 C53 H53 119.9 . . ?
N28 C29 C30 110.53(18) . . ?
N28 C29 H29A 109.5 . . ?
C30 C29 H29A 109.5 . . ?
N28 C29 H29B 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 108.1 . . ?
N41 C46 C57 110.48(19) . . ?
N41 C46 C47 112.54(19) . . ?
C57 C46 C47 110.8(2) . . ?
N41 C46 H46 107.6 . . ?
C57 C46 H46 107.6 . . ?
C47 C46 H46 107.6 . . ?
C22 C23 C18 121.0(2) . . ?
C22 C23 H23 119.5 . . ?
C18 C23 H23 119.5 . . ?
C26 C27 C25A 60.9(2) . . ?
C26 C27 C25B 63.8(2) . . ?
C26 C27 H27A 117.7 . . ?
C25A C27 H27A 117.7 . . ?
C26 C27 H27B 117.7 . . ?
C25A C27 H27B 117.7 . . ?
H27A C27 H27B 114.8 . . ?
C20 C19 C18 120.3(2) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C60 C61 C62 119.4(3) . . ?
C60 C61 H61 120.3 . . ?
C62 C61 H61 120.3 . . ?
C63 C58 C59 117.5(2) . . ?
C63 C58 C57 122.1(2) . . ?
C59 C58 C57 120.4(2) . . ?
C32 C31 C30 119.1(2) . . ?
C32 C31 H31 120.5 . . ?
C30 C31 H31 120.5 . . ?
C23 C22 C21 119.8(3) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C21 C20 C19 120.3(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C67 C66 C65A 63.0(2) . . ?
C67 C66 C65B 61.37(17) . . ?
C67 C66 H66A 117.5 . . ?
C65A C66 H66A 117.5 . . ?
C67 C66 H66B 117.5 . . ?
C65A C66 H66B 117.5 . . ?
H66A C66 H66B 114.5 . . ?
C62 C63 C58 121.5(3) . . ?
C62 C63 H63 119.3 . . ?
C58 C63 H63 119.3 . . ?
C11 C16 C15 120.6(2) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C66 C67 C65B 62.31(18) . . ?
C66 C67 C65A 61.2(2) . . ?
C66 C67 H67A 117.6 . . ?
C65A C67 H67A 117.6 . . ?
C66 C67 H67B 117.6 . . ?
C65A C67 H67B 117.6 . . ?
H67A C67 H67B 114.7 . . ?
C20 C21 C22 119.8(2) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C60 C59 C58 121.1(3) . . ?
C60 C59 H59 119.5 . . ?
C58 C59 H59 119.5 . . ?
C58 C57 C46 113.1(2) . . ?
C58 C57 H57A 109 . . ?
C46 C57 H57A 109 . . ?
C58 C57 H57B 109 . . ?
C46 C57 H57B 109 . . ?
H57A C57 H57B 107.8 . . ?
C61 C62 C63 120.1(3) . . ?
C61 C62 H62 119.9 . . ?
C63 C62 H62 119.9 . . ?
C27 C26 C25A 59.9(2) . . ?
C27 C26 C25B 61.4(2) . . ?
C27 C26 H26A 117.8 . . ?
C25A C26 H26A 117.8 . . ?
C27 C26 H26B 117.8 . . ?
C25A C26 H26B 117.8 . . ?
H26A C26 H26B 114.9 . . ?
C54 C55 C56 120.2(3) . . ?
C54 C55 H55 119.9 . . ?
C56 C55 H55 119.9 . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C14 C15 C16 119.8(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C53 C54 C55 119.9(3) . . ?
C53 C54 H54 120 . . ?
C55 C54 H54 120 . . ?
C61 C60 C59 120.4(3) . . ?
C61 C60 H60 119.8 . . ?
C59 C60 H60 119.8 . . ?
C13 C14 C15 119.7(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
N28 C24A C25A 117.1(4) . . ?
N28 C24A C5 104.0(4) . . ?
C25A C24A C5 108.2(4) . . ?
N28 C24A H24A 109.1 . . ?
C25A C24A H24A 109.1 . . ?
C5 C24A H24A 109.1 . . ?
C24A C25A C27 113.8(4) . . ?
C24A C25A C26 113.4(4) . . ?
C27 C25A C26 59.2(2) . . ?
C24A C25A H25A 118.9 . . ?
C27 C25A H25A 118.9 . . ?
C26 C25A H25A 118.9 . . ?
N28 C24B C5 105.9(4) . . ?
N28 C24B C25B 107.0(5) . . ?
C5 C24B C25B 105.4(5) . . ?
N28 C24B H24B 112.7 . . ?
C5 C24B H24B 112.7 . . ?
C25B C24B H24B 112.7 . . ?
C24B C25B C27 112.0(4) . . ?
C24B C25B C26 109.4(4) . . ?
C27 C25B C26 54.8(2) . . ?
C24B C25B H25B 121 . . ?
C27 C25B H25B 121 . . ?
C26 C25B H25B 121 . . ?
N68 C64A C65A 110.9(7) . . ?
N68 C64A C45 106.8(8) . . ?
C65A C64A C45 105.9(7) . . ?
N68 C64A H64A 111 . . ?
C65A C64A H64A 111 . . ?
C45 C64A H64A 111 . . ?
C64A C65A C66 113.4(6) . . ?
C64A C65A C67 112.3(6) . . ?
C66 C65A C67 55.7(2) . . ?
C64A C65A H65A 119.8 . . ?
C66 C65A H65A 119.8 . . ?
C67 C65A H65A 119.8 . . ?
N68 C64B C65B 116.0(5) . . ?
N68 C64B C45 107.1(4) . . ?
C65B C64B C45 107.2(4) . . ?
N68 C64B H64B 108.8 . . ?
C65B C64B H64B 108.8 . . ?
C45 C64B H64B 108.8 . . ?
C64B C65B C67 111.2(4) . . ?
C64B C65B C66 111.3(4) . . ?
C67 C65B C66 56.32(18) . . ?
C64B C65B H65B 120.5 . . ?
C67 C65B H65B 120.5 . . ?
C66 C65B H65B 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N43 N42 N41 C45 1.1(2) . . . . ?
N43 N42 N41 C46 177.17(18) . . . . ?
N41 N42 N43 N44 -0.8(2) . . . . ?
C45 N44 N43 N42 0.1(2) . . . . ?
N4 N3 N2 N1 0.3(2) . . . . ?
C5 N1 N2 N3 -0.5(2) . . . . ?
C6 N1 N2 N3 -173.85(17) . . . . ?
N2 N3 N4 C5 0.0(2) . . . . ?
N43 N44 C45 N41 0.6(2) . . . . ?
N43 N44 C45 C64B -172.4(4) . . . . ?
N43 N44 C45 C64A 173.0(5) . . . . ?
N42 N41 C45 N44 -1.1(2) . . . . ?
C46 N41 C45 N44 -176.5(2) . . . . ?
N42 N41 C45 C64B 172.8(3) . . . . ?
C46 N41 C45 C64B -2.6(4) . . . . ?
N42 N41 C45 C64A -171.5(7) . . . . ?
C46 N41 C45 C64A 13.1(7) . . . . ?
C7 N9 C10 C11 -90.7(3) . . . . ?
N9 C10 C11 C12 13.0(3) . . . . ?
N9 C10 C11 C16 -169.0(2) . . . . ?
C72 C71 C70 C75 -1.2(4) . . . . ?
C72 C71 C70 C69 -179.1(2) . . . . ?
C5 N1 C6 C17 -113.9(2) . . . . ?
N2 N1 C6 C17 57.5(2) . . . . ?
C5 N1 C6 C7 118.3(2) . . . . ?
N2 N1 C6 C7 -70.2(2) . . . . ?
C52 C51 C56 C55 1.0(4) . . . . ?
C50 C51 C56 C55 179.1(3) . . . . ?
F73 C73 C74 F74 0.6(4) . . . . ?
C72 C73 C74 F74 179.9(2) . . . . ?
F73 C73 C74 C75 -179.6(2) . . . . ?
C72 C73 C74 C75 -0.2(4) . . . . ?
C50 N49 C47 O48 6.2(4) . . . . ?
C50 N49 C47 C46 -175.6(2) . . . . ?
F33 C33 C34 F34 0.6(4) . . . . ?
C32 C33 C34 F34 -179.8(2) . . . . ?
F33 C33 C34 C35 179.9(2) . . . . ?
C32 C33 C34 C35 -0.5(4) . . . . ?
F73 C73 C72 F72 0.4(4) . . . . ?
C74 C73 C72 F72 -179.0(2) . . . . ?
F73 C73 C72 C71 -179.7(2) . . . . ?
C74 C73 C72 C71 1.0(4) . . . . ?
C70 C71 C72 F72 179.7(2) . . . . ?
C70 C71 C72 C73 -0.3(4) . . . . ?
C47 N49 C50 C51 94.8(3) . . . . ?
C56 C51 C50 N49 173.8(2) . . . . ?
C52 C51 C50 N49 -8.2(3) . . . . ?
C16 C11 C12 C13 0.3(4) . . . . ?
C10 C11 C12 C13 178.2(2) . . . . ?
F33 C33 C32 F32 0.2(4) . . . . ?
C34 C33 C32 F32 -179.4(2) . . . . ?
F33 C33 C32 C31 179.7(2) . . . . ?
C34 C33 C32 C31 0.1(4) . . . . ?
F74 C74 C75 C70 178.6(2) . . . . ?
C73 C74 C75 C70 -1.2(4) . . . . ?
C71 C70 C75 C74 1.9(4) . . . . ?
C69 C70 C75 C74 180.0(2) . . . . ?
C10 N9 C7 O8 6.0(4) . . . . ?
C10 N9 C7 C6 -169.1(2) . . . . ?
N1 C6 C7 O8 162.6(2) . . . . ?
C17 C6 C7 O8 36.3(3) . . . . ?
N1 C6 C7 N9 -22.1(3) . . . . ?
C17 C6 C7 N9 -148.3(2) . . . . ?
N3 N4 C5 N1 -0.3(2) . . . . ?
N3 N4 C5 C24B -169.5(4) . . . . ?
N3 N4 C5 C24A 173.5(4) . . . . ?
N2 N1 C5 N4 0.6(2) . . . . ?
C6 N1 C5 N4 172.6(2) . . . . ?
N2 N1 C5 C24B 166.8(5) . . . . ?
C6 N1 C5 C24B -21.1(6) . . . . ?
N2 N1 C5 C24A -174.5(3) . . . . ?
C6 N1 C5 C24A -2.4(4) . . . . ?
C56 C51 C52 C53 -1.4(4) . . . . ?
C50 C51 C52 C53 -179.4(2) . . . . ?
C64A N68 C69 C70 -161.0(5) . . . . ?
C64B N68 C69 C70 176.8(3) . . . . ?
C75 C70 C69 N68 150.9(2) . . . . ?
C71 C70 C69 N68 -31.1(3) . . . . ?
F34 C34 C35 C30 179.9(2) . . . . ?
C33 C34 C35 C30 0.7(4) . . . . ?
C31 C30 C35 C34 -0.4(3) . . . . ?
C29 C30 C35 C34 -179.5(2) . . . . ?
C23 C18 C17 C6 -97.2(3) . . . . ?
C19 C18 C17 C6 79.5(3) . . . . ?
N1 C6 C17 C18 66.2(2) . . . . ?
C7 C6 C17 C18 -165.77(19) . . . . ?
C51 C52 C53 C54 1.0(4) . . . . ?
C24A N28 C29 C30 -167.7(3) . . . . ?
C24B N28 C29 C30 167.4(4) . . . . ?
C35 C30 C29 N28 -147.8(2) . . . . ?
C31 C30 C29 N28 33.1(3) . . . . ?
C45 N41 C46 C57 112.6(3) . . . . ?
N42 N41 C46 C57 -62.4(3) . . . . ?
C45 N41 C46 C47 -123.0(2) . . . . ?
N42 N41 C46 C47 62.0(3) . . . . ?
O48 C47 C46 N41 -155.5(2) . . . . ?
N49 C47 C46 N41 26.2(3) . . . . ?
O48 C47 C46 C57 -31.2(3) . . . . ?
N49 C47 C46 C57 150.4(2) . . . . ?
C19 C18 C23 C22 0.5(4) . . . . ?
C17 C18 C23 C22 177.2(2) . . . . ?
C23 C18 C19 C20 0.7(4) . . . . ?
C17 C18 C19 C20 -176.2(2) . . . . ?
F32 C32 C31 C30 179.7(2) . . . . ?
C33 C32 C31 C30 0.2(4) . . . . ?
C35 C30 C31 C32 0.0(4) . . . . ?
C29 C30 C31 C32 179.1(2) . . . . ?
C18 C23 C22 C21 -1.0(4) . . . . ?
C18 C19 C20 C21 -1.3(4) . . . . ?
C59 C58 C63 C62 -1.0(4) . . . . ?
C57 C58 C63 C62 -179.8(2) . . . . ?
C12 C11 C16 C15 -0.2(4) . . . . ?
C10 C11 C16 C15 -178.2(3) . . . . ?
C19 C20 C21 C22 0.8(4) . . . . ?
C23 C22 C21 C20 0.4(4) . . . . ?
C63 C58 C59 C60 0.3(4) . . . . ?
C57 C58 C59 C60 179.1(3) . . . . ?
C63 C58 C57 C46 104.7(3) . . . . ?
C59 C58 C57 C46 -74.0(3) . . . . ?
N41 C46 C57 C58 -55.2(3) . . . . ?
C47 C46 C57 C58 179.4(2) . . . . ?
C60 C61 C62 C63 0.2(5) . . . . ?
C58 C63 C62 C61 0.7(4) . . . . ?
C51 C56 C55 C54 -0.2(5) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C11 C16 C15 C14 -0.2(5) . . . . ?
C52 C53 C54 C55 -0.1(5) . . . . ?
C56 C55 C54 C53 -0.2(5) . . . . ?
C62 C61 C60 C59 -0.9(5) . . . . ?
C58 C59 C60 C61 0.7(5) . . . . ?
C12 C13 C14 C15 -0.4(5) . . . . ?
C16 C15 C14 C13 0.5(5) . . . . ?
C29 N28 C24A C25A -59.7(5) . . . . ?
C29 N28 C24A C5 -179.1(3) . . . . ?
N4 C5 C24A N28 118.1(4) . . . . ?
N1 C5 C24A N28 -68.4(4) . . . . ?
N4 C5 C24A C25A -7.1(6) . . . . ?
N1 C5 C24A C25A 166.3(3) . . . . ?
N28 C24A C25A C27 93.4(5) . . . . ?
C5 C24A C25A C27 -149.5(3) . . . . ?
N28 C24A C25A C26 158.6(4) . . . . ?
C5 C24A C25A C26 -84.3(5) . . . . ?
C26 C27 C25A C24A 104.0(4) . . . . ?
C27 C26 C25A C24A -104.7(4) . . . . ?
C29 N28 C24B C5 161.5(3) . . . . ?
C29 N28 C24B C25B 49.5(6) . . . . ?
N4 C5 C24B N28 138.9(3) . . . . ?
N1 C5 C24B N28 -26.7(7) . . . . ?
N4 C5 C24B C25B -108.0(4) . . . . ?
N1 C5 C24B C25B 86.5(5) . . . . ?
N28 C24B C25B C27 -100.7(5) . . . . ?
C5 C24B C25B C27 146.9(4) . . . . ?
N28 C24B C25B C26 -159.6(4) . . . . ?
C5 C24B C25B C26 88.1(5) . . . . ?
C26 C27 C25B C24B -98.8(4) . . . . ?
C27 C26 C25B C24B 103.8(4) . . . . ?
C69 N68 C64A C65A -47.7(8) . . . . ?
C69 N68 C64A C45 -162.6(4) . . . . ?
N44 C45 C64A N68 -137.2(4) . . . . ?
N41 C45 C64A N68 32.7(10) . . . . ?
N44 C45 C64A C65A 104.5(6) . . . . ?
N41 C45 C64A C65A -85.6(9) . . . . ?
N68 C64A C65A C66 98.8(7) . . . . ?
C45 C64A C65A C66 -145.7(5) . . . . ?
N68 C64A C65A C67 159.7(5) . . . . ?
C45 C64A C65A C67 -84.7(7) . . . . ?
C67 C66 C65A C64A 101.8(6) . . . . ?
C66 C67 C65A C64A -103.9(6) . . . . ?
C69 N68 C64B C65B 59.3(5) . . . . ?
C69 N68 C64B C45 178.9(3) . . . . ?
N44 C45 C64B N68 -117.5(4) . . . . ?
N41 C45 C64B N68 70.2(4) . . . . ?
N44 C45 C64B C65B 7.6(6) . . . . ?
N41 C45 C64B C65B -164.7(3) . . . . ?
N68 C64B C65B C67 -153.7(4) . . . . ?
C45 C64B C65B C67 86.8(4) . . . . ?
N68 C64B C65B C66 -92.8(5) . . . . ?
C45 C64B C65B C66 147.6(3) . . . . ?
C66 C67 C65B C64B 102.1(4) . . . . ?
C67 C66 C65B C64B -101.9(4) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_new
_database_code_depnum_ccdc_archive 'CCDC 1844783'
loop_
_audit_author_name
_audit_author_address
'Justyna Kalinowska-Tluscik'
;Jagiellonian University
Poland
;
_audit_update_record             
;
2018-05-22 deposited with the CCDC.	2020-01-07 downloaded from the CCDC.
;

_audit_creation_date             2018-02-22T22:14:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C44 H54 Cl2 N12 O2'
_chemical_formula_moiety         'C22 H27 Cl N6 O'
_chemical_formula_weight         853.89

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.7643(6)
_cell_length_b                   14.0058(6)
_cell_length_c                   15.9242(8)
_cell_angle_alpha                89.704(4)
_cell_angle_beta                 78.054(4)
_cell_angle_gamma                67.659(5)
_cell_volume                     2165.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    6522
_cell_measurement_theta_min      3.392
_cell_measurement_theta_max      71.3

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            grey
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.31
_exptl_crystal_F_000             904

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.4274
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.417
_shelx_estimated_absorpt_T_max   0.843

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_ambient_temperature      130(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0363276
_diffrn_orient_matrix_ub_12      0.0219001
_diffrn_orient_matrix_ub_13      -0.0949181
_diffrn_orient_matrix_ub_21      0.1080437
_diffrn_orient_matrix_ub_22      -0.1117259
_diffrn_orient_matrix_ub_23      -0.0208225
_diffrn_orient_matrix_ub_31      -0.1103913
_diffrn_orient_matrix_ub_32      -0.035692
_diffrn_orient_matrix_ub_33      -0.0200037
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_number            13358
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.423
_diffrn_reflns_theta_max         71.392
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.946
_reflns_Friedel_coverage         0
_reflns_number_total             7978
_reflns_number_gt                6808
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0874P)²+0.7419P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7978
_refine_ls_number_parameters     620
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1493
_refine_ls_wR_factor_gt          0.138
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.057

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl43 Cl 0.71630(7) 0.27966(6) 0.71087(4) 0.04818(18) Uani 1 1 d . . . . .
Cl13 Cl 0.64187(6) 0.84896(5) 0.26334(4) 0.04254(16) Uani 1 1 d . . . . .
O9 O 0.87042(15) 0.56527(11) 0.42934(10) 0.0301(3) Uani 1 1 d . . . . .
O39 O 0.88041(15) 0.04984(12) 0.91234(10) 0.0320(3) Uani 1 1 d . . . . .
N3 N 0.49053(17) 0.55583(13) 0.64737(12) 0.0282(4) Uani 1 1 d . . . . .
N32 N 0.57446(17) 0.01265(13) 1.09095(12) 0.0270(4) Uani 1 1 d . . . . .
N31 N 0.69056(16) 0.02855(12) 1.09163(11) 0.0228(3) Uani 1 1 d . . . . .
N40 N 0.74054(17) 0.00020(13) 0.85145(12) 0.0270(4) Uani 1 1 d . . . . .
N4 N 0.54188(18) 0.61401(14) 0.68707(12) 0.0301(4) Uani 1 1 d . . . . .
N2 N 0.58832(16) 0.48358(13) 0.59418(11) 0.0251(3) Uani 1 1 d . . . . .
N10 N 0.71804(17) 0.53819(13) 0.36392(12) 0.0260(4) Uani 1 1 d . . . . .
N33 N 0.47304(17) 0.09740(14) 1.12454(12) 0.0284(4) Uani 1 1 d . . . . .
N52 N 0.69403(18) 0.28720(14) 1.12916(12) 0.0294(4) Uani 1 1 d . . . . .
N34 N 0.51892(17) 0.16924(13) 1.14756(12) 0.0274(4) Uani 1 1 d . . . . .
N1 N 0.70621(16) 0.49448(12) 0.59895(11) 0.0227(3) Uani 1 1 d . . . . .
C5 C 0.6768(2) 0.57441(15) 0.65543(13) 0.0253(4) Uani 1 1 d D . . . .
C12 C 0.57452(19) 0.72633(15) 0.38196(13) 0.0239(4) Uani 1 1 d . . . . .
C35 C 0.65502(19) 0.12483(15) 1.12699(12) 0.0228(4) Uani 1 1 d . . . . .
C48 C 0.74876(19) 0.17724(15) 1.14393(13) 0.0238(4) Uani 1 1 d . . . . .
H48 H 0.8408 0.1427 1.1039 0.029 Uiso 1 1 calc R U . . .
C11 C 0.6860(2) 0.63501(16) 0.32482(14) 0.0285(4) Uani 1 1 d . . . . .
H11A H 0.6562 0.6282 0.2711 0.034 Uiso 1 1 calc R U . . .
H11B H 0.7707 0.6494 0.3089 0.034 Uiso 1 1 calc R U . . .
C57 C 1.0671(2) 0.33893(16) 0.90076(15) 0.0329(5) Uani 1 1 d . . . . .
H57 H 1.1475 0.3471 0.8698 0.039 Uiso 1 1 calc R U . . .
C55 C 0.8788(2) 0.28507(15) 0.90432(15) 0.0297(4) Uani 1 1 d . . . . .
H55 H 0.8317 0.2555 0.8752 0.036 Uiso 1 1 calc R U . . .
C36 C 0.8245(2) -0.05579(15) 1.05825(14) 0.0266(4) Uani 1 1 d . . . . .
H36A H 0.8372 -0.1133 1.0963 0.032 Uiso 1 1 calc R U . . .
H36B H 0.8991 -0.0307 1.0577 0.032 Uiso 1 1 calc R U . . .
C17 C 0.4946(2) 0.71388(15) 0.45877(14) 0.0266(4) Uani 1 1 d . . . . .
H17 H 0.51 0.6461 0.4761 0.032 Uiso 1 1 calc R U . . .
C37 C 0.83265(19) -0.09479(14) 0.96732(14) 0.0260(4) Uani 1 1 d . . . . .
H37A H 0.9215 -0.1539 0.9463 0.031 Uiso 1 1 calc R U . . .
H37B H 0.7573 -0.119 0.9677 0.031 Uiso 1 1 calc R U . . .
C8 C 0.80906(18) 0.51084(14) 0.41513(13) 0.0233(4) Uani 1 1 d . . . . .
C42 C 0.6085(2) 0.18682(16) 0.83956(13) 0.0262(4) Uani 1 1 d . . . . .
C54 C 0.8289(2) 0.31621(14) 0.99167(14) 0.0258(4) Uani 1 1 d . . . . .
C47 C 0.5126(2) 0.19208(16) 0.91505(14) 0.0273(4) Uani 1 1 d . . . . .
H47 H 0.5154 0.1301 0.9406 0.033 Uiso 1 1 calc R U . . .
C59 C 0.9003(2) 0.35871(15) 1.03352(14) 0.0279(4) Uani 1 1 d . . . . .
H59 H 0.8676 0.3806 1.0932 0.033 Uiso 1 1 calc R U . . .
C41 C 0.7156(2) 0.08422(17) 0.79562(14) 0.0318(4) Uani 1 1 d . . . . .
H41A H 0.685 0.0654 0.7459 0.038 Uiso 1 1 calc R U . . .
H41B H 0.8032 0.0928 0.773 0.038 Uiso 1 1 calc R U . . .
C56 C 0.9964(2) 0.29665(16) 0.85905(15) 0.0340(5) Uani 1 1 d . . . . .
H56 H 1.0287 0.2756 0.7993 0.041 Uiso 1 1 calc R U . . .
C6 C 0.83871(19) 0.42012(15) 0.54857(14) 0.0272(4) Uani 1 1 d . . . . .
H6A H 0.8606 0.3519 0.5727 0.033 Uiso 1 1 calc R U . . .
H6B H 0.9128 0.4443 0.5524 0.033 Uiso 1 1 calc R U . . .
C58 C 1.0193(2) 0.36917(16) 0.98813(16) 0.0312(4) Uani 1 1 d . . . . .
H58 H 1.068 0.3972 1.0172 0.037 Uiso 1 1 calc R U . . .
C43 C 0.5998(2) 0.28033(18) 0.80491(15) 0.0316(5) Uani 1 1 d . . . . .
C38 C 0.82053(18) -0.00853(14) 0.90810(13) 0.0239(4) Uani 1 1 d . . . . .
C7 C 0.8326(2) 0.40904(14) 0.45484(14) 0.0267(4) Uani 1 1 d . . . . .
H7A H 0.9201 0.3554 0.4227 0.032 Uiso 1 1 calc R U . . .
H7B H 0.7569 0.3867 0.451 0.032 Uiso 1 1 calc R U . . .
C53 C 0.6956(2) 0.30875(17) 1.03923(15) 0.0313(4) Uani 1 1 d . . . . .
H53A H 0.618 0.3748 1.0369 0.038 Uiso 1 1 calc R U . . .
H53B H 0.6813 0.2532 1.0094 0.038 Uiso 1 1 calc R U . . .
C46 C 0.4130(2) 0.28640(17) 0.95342(15) 0.0316(4) Uani 1 1 d . . . . .
H46 H 0.3482 0.2881 1.0045 0.038 Uiso 1 1 calc R U . . .
C49 C 0.7677(2) 0.16533(17) 1.23753(13) 0.0294(4) Uani 1 1 d . . . . .
H49 H 0.6756 0.2031 1.2767 0.035 Uiso 1 1 calc R U . . .
C13 C 0.5467(2) 0.82756(17) 0.35927(14) 0.0297(4) Uani 1 1 d . . . . .
C45 C 0.4073(2) 0.37811(17) 0.91798(17) 0.0373(5) Uani 1 1 d . . . . .
H45 H 0.3394 0.4424 0.9448 0.045 Uiso 1 1 calc R U . . .
C14 C 0.4466(2) 0.91263(18) 0.41048(18) 0.0412(5) Uani 1 1 d . . . . .
H14 H 0.4314 0.9806 0.3936 0.049 Uiso 1 1 calc R U . . .
C51 C 0.8181(3) 0.05306(19) 1.25913(15) 0.0382(5) Uani 1 1 d . . . . .
H51A H 0.9056 0.0129 1.2191 0.057 Uiso 1 1 calc R U . . .
H51B H 0.7496 0.0245 1.254 0.057 Uiso 1 1 calc R U . . .
H51C H 0.8318 0.0493 1.3182 0.057 Uiso 1 1 calc R U . . .
C44 C 0.5013(3) 0.37532(18) 0.84311(17) 0.0388(5) Uani 1 1 d . . . . .
H44 H 0.4984 0.4376 0.8181 0.047 Uiso 1 1 calc R U . . .
C16 C 0.3934(2) 0.79824(18) 0.51049(15) 0.0347(5) Uani 1 1 d . . . . .
H16 H 0.3404 0.7879 0.5627 0.042 Uiso 1 1 calc R U . . .
C50 C 0.8637(2) 0.2158(2) 1.25462(16) 0.0394(5) Uani 1 1 d . . . . .
H50A H 0.8655 0.2153 1.3159 0.059 Uiso 1 1 calc R U . . .
H50B H 0.8306 0.2874 1.2387 0.059 Uiso 1 1 calc R U . . .
H50C H 0.9568 0.1771 1.2202 0.059 Uiso 1 1 calc R U . . .
C15 C 0.3692(2) 0.89804(18) 0.48596(18) 0.0425(6) Uani 1 1 d . . . . .
H15 H 0.2996 0.9559 0.5212 0.051 Uiso 1 1 calc R U . . .
C18 C 0.7791(2) 0.61390(17) 0.68032(14) 0.0293(4) Uani 1 1 d D . . . .
C19 C 0.8437(2) 0.55229(15) 0.75149(13) 0.0265(4) Uani 1 1 d D . . . .
H19 H 0.8994 0.4794 0.7266 0.032 Uiso 1 1 calc R U . . .
C21 C 0.7372(2) 0.54882(19) 0.82968(15) 0.0358(5) Uani 1 1 d . . . . .
H21A H 0.6727 0.6195 0.8509 0.054 Uiso 1 1 calc R U . . .
H21B H 0.7837 0.5154 0.8751 0.054 Uiso 1 1 calc R U . . .
H21C H 0.6866 0.5093 0.8134 0.054 Uiso 1 1 calc R U . . .
C20 C 0.9421(2) 0.5947(2) 0.77855(15) 0.0384(5) Uani 1 1 d . . . . .
H20A H 0.9975 0.5457 0.8136 0.058 Uiso 1 1 calc R U . . .
H20B H 0.8889 0.6614 0.8123 0.058 Uiso 1 1 calc R U . . .
H20C H 1.0029 0.6042 0.7272 0.058 Uiso 1 1 calc R U . . .
N22A N 0.7206(2) 0.72299(15) 0.70380(14) 0.0263(5) Uani 0.846(4) 1 d D . P A 1
C23A C 0.6726(3) 0.7879(2) 0.6359(2) 0.0340(6) Uani 0.846(4) 1 d . . P A 1
H23A H 0.5959 0.8531 0.6625 0.041 Uiso 0.846(4) 1 calc R U P A 1
H23B H 0.6365 0.7517 0.6 0.041 Uiso 0.846(4) 1 calc R U P A 1
C24A C 0.7855(3) 0.8138(2) 0.5786(3) 0.0252(7) Uani 0.846(4) 1 d . . P A 1
C25A C 0.8070(4) 0.8038(2) 0.4891(4) 0.0329(8) Uani 0.846(4) 1 d . . P A 1
H25 H 0.7528 0.7775 0.4637 0.039 Uiso 0.846(4) 1 calc R U P A 1
C26A C 0.9062(5) 0.8314(3) 0.4363(3) 0.0400(10) Uani 0.846(4) 1 d . . P A 1
H26 H 0.9193 0.824 0.3754 0.048 Uiso 0.846(4) 1 calc R U P A 1
C27A C 0.9854(3) 0.8696(2) 0.4726(3) 0.0391(7) Uani 0.846(4) 1 d . . P A 1
H27 H 1.0529 0.8891 0.4369 0.047 Uiso 0.846(4) 1 calc R U P A 1
C28A C 0.9660(3) 0.8795(2) 0.5614(2) 0.0357(7) Uani 0.846(4) 1 d . . P A 1
H28 H 1.0208 0.9055 0.5865 0.043 Uiso 0.846(4) 1 calc R U P A 1
C29A C 0.8669(3) 0.8516(2) 0.6140(2) 0.0289(6) Uani 0.846(4) 1 d . . P A 1
H29 H 0.8549 0.8585 0.6748 0.035 Uiso 0.846(4) 1 calc R U P A 1
N22B N 0.8192(12) 0.6704(9) 0.6241(8) 0.030(3) Uani 0.154(4) 1 d D . P A 2
C23B C 0.7293(17) 0.7704(12) 0.5945(13) 0.0340(6) Uani 0.154(4) 1 d D . P A 2
H23C H 0.6655 0.758 0.5634 0.041 Uiso 0.154(4) 1 calc R U P A 2
H23D H 0.6742 0.821 0.6446 0.041 Uiso 0.154(4) 1 calc R U P A 2
C26B C 0.939(2) 0.8412(14) 0.3995(14) 0.031(4) Uani 0.154(4) 1 d . . P A 2
H26B H 0.9507 0.8376 0.3386 0.037 Uiso 0.154(4) 1 calc R U P A 2
C27B C 1.0146(19) 0.8814(14) 0.4378(14) 0.0391(7) Uani 0.154(4) 1 d . . P A 2
H27B H 1.0821 0.9032 0.405 0.047 Uiso 0.154(4) 1 calc R U P A 2
C24B C 0.8198(18) 0.8095(12) 0.5380(17) 0.021(3) Uani 0.154(4) 1 d . . P A 2
C25B C 0.847(2) 0.8065(15) 0.4489(17) 0.030(4) Uani 0.154(4) 1 d . . P A 2
H25B H 0.7977 0.7784 0.42 0.036 Uiso 0.154(4) 1 calc R U P A 2
C29B C 0.9029(19) 0.8519(13) 0.5777(13) 0.0289(6) Uani 0.154(4) 1 d . . P A 2
H29B H 0.8971 0.8533 0.638 0.035 Uiso 0.154(4) 1 calc R U P A 2
C28B C 0.986(2) 0.8880(17) 0.5258(18) 0.0357(7) Uani 0.154(4) 1 d . . P A 2
H28B H 1.0306 0.9219 0.5529 0.043 Uiso 0.154(4) 1 calc R U P A 2
H22A H 0.644(3) 0.736(2) 0.746(2) 0.030(7) Uiso 0.846(4) 1 d . . P A 1
H18A H 0.853(2) 0.598(2) 0.6253(12) 0.028(7) Uiso 0.846(4) 1 d D . P A 1
H22B H 0.884(8) 0.638(4) 0.576(3) 0.034 Uiso 0.154(4) 1 d D U P A 2
H18B H 0.705(4) 0.666(3) 0.729(2) 0.034 Uiso 0.154(4) 1 d D U P A 2
H10 H 0.677(2) 0.5014(19) 0.3568(15) 0.023(6) Uiso 1 1 d . . . . .
H40 H 0.697(3) -0.040(2) 0.8534(17) 0.033(7) Uiso 1 1 d . . . . .
H52 H 0.599(3) 0.324(3) 1.163(2) 0.055(9) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl43 C43 1.740(2) . ?
Cl13 C13 1.748(2) . ?
O9 C8 1.231(2) . ?
O39 C38 1.228(2) . ?
N3 N2 1.296(2) . ?
N3 N4 1.364(2) . ?
N32 N33 1.291(2) . ?
N32 N31 1.352(2) . ?
N31 C35 1.345(2) . ?
N31 C36 1.467(2) . ?
N40 C38 1.346(3) . ?
N40 C41 1.447(3) . ?
N40 H40 0.86(3) . ?
N4 C5 1.326(3) . ?
N2 N1 1.352(2) . ?
N10 C8 1.347(3) . ?
N10 C11 1.439(3) . ?
N10 H10 0.82(2) . ?
N33 N34 1.359(2) . ?
N52 C53 1.460(3) . ?
N52 C48 1.462(2) . ?
N52 H52 0.99(3) . ?
N34 C35 1.323(3) . ?
N1 C5 1.336(3) . ?
N1 C6 1.472(2) . ?
C5 C18 1.523(3) . ?
C12 C17 1.394(3) . ?
C12 C13 1.395(3) . ?
C12 C11 1.515(3) . ?
C35 C48 1.519(2) . ?
C48 C49 1.546(3) . ?
C48 H48 1 . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C57 C58 1.387(3) . ?
C57 C56 1.388(3) . ?
C57 H57 0.95 . ?
C55 C56 1.388(3) . ?
C55 C54 1.390(3) . ?
C55 H55 0.95 . ?
C36 C37 1.524(3) . ?
C36 H36A 0.99 . ?
C36 H36B 0.99 . ?
C17 C16 1.386(3) . ?
C17 H17 0.95 . ?
C37 C38 1.512(3) . ?
C37 H37A 0.99 . ?
C37 H37B 0.99 . ?
C8 C7 1.510(3) . ?
C42 C47 1.395(3) . ?
C42 C43 1.396(3) . ?
C42 C41 1.517(3) . ?
C54 C59 1.398(3) . ?
C54 C53 1.519(3) . ?
C47 C46 1.388(3) . ?
C47 H47 0.95 . ?
C59 C58 1.394(3) . ?
C59 H59 0.95 . ?
C41 H41A 0.99 . ?
C41 H41B 0.99 . ?
C56 H56 0.95 . ?
C6 C7 1.519(3) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C58 H58 0.95 . ?
C43 C44 1.391(3) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C53 H53A 0.99 . ?
C53 H53B 0.99 . ?
C46 C45 1.385(3) . ?
C46 H46 0.95 . ?
C49 C51 1.519(3) . ?
C49 C50 1.521(3) . ?
C49 H49 1 . ?
C13 C14 1.384(3) . ?
C45 C44 1.385(4) . ?
C45 H45 0.95 . ?
C14 C15 1.376(4) . ?
C14 H14 0.95 . ?
C51 H51A 0.98 . ?
C51 H51B 0.98 . ?
C51 H51C 0.98 . ?
C44 H44 0.95 . ?
C16 C15 1.391(3) . ?
C16 H16 0.95 . ?
C50 H50A 0.98 . ?
C50 H50B 0.98 . ?
C50 H50C 0.98 . ?
C15 H15 0.95 . ?
C18 N22B 1.307(12) . ?
C18 N22A 1.431(3) . ?
C18 C19 1.540(3) . ?
C18 H18A 1.014(16) . ?
C18 H18B 1.038(18) . ?
C19 C21 1.523(3) . ?
C19 C20 1.526(3) . ?
C19 H19 1 . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
N22A C23A 1.458(3) . ?
N22A H22A 0.90(3) . ?
C23A C24A 1.521(4) . ?
C23A H23A 0.99 . ?
C23A H23B 0.99 . ?
C24A C29A 1.388(4) . ?
C24A C25A 1.395(5) . ?
C25A C26A 1.392(6) . ?
C25A H25 0.95 . ?
C26A C27A 1.379(6) . ?
C26A H26 0.95 . ?
C27A C28A 1.386(5) . ?
C27A H27 0.95 . ?
C28A C29A 1.392(4) . ?
C28A H28 0.95 . ?
C29A H29 0.95 . ?
N22B C23B 1.506(19) . ?
N22B H22B 0.91(2) . ?
C23B C24B 1.45(2) . ?
C23B H23C 0.99 . ?
C23B H23D 0.99 . ?
C26B C25B 1.37(3) . ?
C26B C27B 1.38(3) . ?
C26B H26B 0.95 . ?
C27B C28B 1.37(3) . ?
C27B H27B 0.95 . ?
C24B C25B 1.39(3) . ?
C24B C29B 1.48(3) . ?
C25B H25B 0.95 . ?
C29B C28B 1.33(3) . ?
C29B H29B 0.95 . ?
C28B H28B 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N3 N4 110.90(15) . . ?
N33 N32 N31 106.17(15) . . ?
C35 N31 N32 108.67(16) . . ?
C35 N31 C36 132.41(16) . . ?
N32 N31 C36 118.91(15) . . ?
C38 N40 C41 120.30(17) . . ?
C38 N40 H40 118.7(17) . . ?
C41 N40 H40 120.6(17) . . ?
C5 N4 N3 105.85(17) . . ?
N3 N2 N1 106.00(15) . . ?
C8 N10 C11 120.64(16) . . ?
C8 N10 H10 120.4(17) . . ?
C11 N10 H10 118.9(17) . . ?
N32 N33 N34 111.16(15) . . ?
C53 N52 C48 114.82(17) . . ?
C53 N52 H52 108.3(18) . . ?
C48 N52 H52 112.0(18) . . ?
C35 N34 N33 106.00(17) . . ?
C5 N1 N2 109.14(16) . . ?
C5 N1 C6 131.27(16) . . ?
N2 N1 C6 119.53(16) . . ?
N4 C5 N1 108.10(17) . . ?
N4 C5 C18 125.31(19) . . ?
N1 C5 C18 126.59(18) . . ?
C17 C12 C13 116.82(19) . . ?
C17 C12 C11 122.17(17) . . ?
C13 C12 C11 121.01(18) . . ?
N34 C35 N31 107.99(16) . . ?
N34 C35 C48 123.68(17) . . ?
N31 C35 C48 128.31(17) . . ?
N52 C48 C35 111.61(15) . . ?
N52 C48 C49 109.39(16) . . ?
C35 C48 C49 110.09(16) . . ?
N52 C48 H48 108.6 . . ?
C35 C48 H48 108.6 . . ?
C49 C48 H48 108.6 . . ?
N10 C11 C12 114.02(17) . . ?
N10 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
N10 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C58 C57 C56 119.4(2) . . ?
C58 C57 H57 120.3 . . ?
C56 C57 H57 120.3 . . ?
C56 C55 C54 120.89(19) . . ?
C56 C55 H55 119.6 . . ?
C54 C55 H55 119.6 . . ?
N31 C36 C37 110.18(15) . . ?
N31 C36 H36A 109.6 . . ?
C37 C36 H36A 109.6 . . ?
N31 C36 H36B 109.6 . . ?
C37 C36 H36B 109.6 . . ?
H36A C36 H36B 108.1 . . ?
C16 C17 C12 121.48(19) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
C38 C37 C36 109.72(16) . . ?
C38 C37 H37A 109.7 . . ?
C36 C37 H37A 109.7 . . ?
C38 C37 H37B 109.7 . . ?
C36 C37 H37B 109.7 . . ?
H37A C37 H37B 108.2 . . ?
O9 C8 N10 122.38(18) . . ?
O9 C8 C7 121.17(18) . . ?
N10 C8 C7 116.45(16) . . ?
C47 C42 C43 117.0(2) . . ?
C47 C42 C41 121.76(18) . . ?
C43 C42 C41 121.21(19) . . ?
C55 C54 C59 118.71(19) . . ?
C55 C54 C53 120.29(18) . . ?
C59 C54 C53 120.94(19) . . ?
C46 C47 C42 121.12(19) . . ?
C46 C47 H47 119.4 . . ?
C42 C47 H47 119.4 . . ?
C58 C59 C54 120.3(2) . . ?
C58 C59 H59 119.9 . . ?
C54 C59 H59 119.9 . . ?
N40 C41 C42 113.84(17) . . ?
N40 C41 H41A 108.8 . . ?
C42 C41 H41A 108.8 . . ?
N40 C41 H41B 108.8 . . ?
C42 C41 H41B 108.8 . . ?
H41A C41 H41B 107.7 . . ?
C55 C56 C57 120.3(2) . . ?
C55 C56 H56 119.9 . . ?
C57 C56 H56 119.9 . . ?
N1 C6 C7 110.58(16) . . ?
N1 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C57 C58 C59 120.43(19) . . ?
C57 C58 H58 119.8 . . ?
C59 C58 H58 119.8 . . ?
C44 C43 C42 122.4(2) . . ?
C44 C43 Cl43 118.09(17) . . ?
C42 C43 Cl43 119.52(18) . . ?
O39 C38 N40 122.58(19) . . ?
O39 C38 C37 121.30(18) . . ?
N40 C38 C37 116.12(16) . . ?
C8 C7 C6 110.28(16) . . ?
C8 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N52 C53 C54 113.27(17) . . ?
N52 C53 H53A 108.9 . . ?
C54 C53 H53A 108.9 . . ?
N52 C53 H53B 108.9 . . ?
C54 C53 H53B 108.9 . . ?
H53A C53 H53B 107.7 . . ?
C45 C46 C47 120.7(2) . . ?
C45 C46 H46 119.7 . . ?
C47 C46 H46 119.7 . . ?
C51 C49 C50 110.93(19) . . ?
C51 C49 C48 112.51(17) . . ?
C50 C49 C48 110.51(17) . . ?
C51 C49 H49 107.6 . . ?
C50 C49 H49 107.6 . . ?
C48 C49 H49 107.6 . . ?
C14 C13 C12 122.4(2) . . ?
C14 C13 Cl13 118.28(17) . . ?
C12 C13 Cl13 119.33(17) . . ?
C44 C45 C46 119.5(2) . . ?
C44 C45 H45 120.3 . . ?
C46 C45 H45 120.3 . . ?
C15 C14 C13 119.5(2) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C49 C51 H51A 109.5 . . ?
C49 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C49 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C45 C44 C43 119.3(2) . . ?
C45 C44 H44 120.4 . . ?
C43 C44 H44 120.4 . . ?
C17 C16 C15 120.0(2) . . ?
C17 C16 H16 120 . . ?
C15 C16 H16 120 . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C14 C15 C16 119.8(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
N22B C18 C5 114.0(5) . . ?
N22A C18 C5 112.80(18) . . ?
N22B C18 C19 132.1(6) . . ?
N22A C18 C19 111.52(18) . . ?
C5 C18 C19 110.97(16) . . ?
N22A C18 H18A 109.3(16) . . ?
C5 C18 H18A 103.0(15) . . ?
C19 C18 H18A 108.9(15) . . ?
N22B C18 H18B 105(2) . . ?
C5 C18 H18B 93(2) . . ?
C19 C18 H18B 88(2) . . ?
C21 C19 C20 110.41(18) . . ?
C21 C19 C18 113.17(17) . . ?
C20 C19 C18 110.79(17) . . ?
C21 C19 H19 107.4 . . ?
C20 C19 H19 107.4 . . ?
C18 C19 H19 107.4 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 N22A C23A 115.2(2) . . ?
C18 N22A H22A 107.4(19) . . ?
C23A N22A H22A 104.7(19) . . ?
N22A C23A C24A 112.7(2) . . ?
N22A C23A H23A 109 . . ?
C24A C23A H23A 109 . . ?
N22A C23A H23B 109 . . ?
C24A C23A H23B 109 . . ?
H23A C23A H23B 107.8 . . ?
C29A C24A C25A 118.1(3) . . ?
C29A C24A C23A 120.8(3) . . ?
C25A C24A C23A 121.0(3) . . ?
C26A C25A C24A 121.4(3) . . ?
C26A C25A H25 119.3 . . ?
C24A C25A H25 119.3 . . ?
C27A C26A C25A 119.8(4) . . ?
C27A C26A H26 120.1 . . ?
C25A C26A H26 120.1 . . ?
C26A C27A C28A 119.6(3) . . ?
C26A C27A H27 120.2 . . ?
C28A C27A H27 120.2 . . ?
C27A C28A C29A 120.5(3) . . ?
C27A C28A H28 119.8 . . ?
C29A C28A H28 119.8 . . ?
C24A C29A C28A 120.7(3) . . ?
C24A C29A H29 119.7 . . ?
C28A C29A H29 119.7 . . ?
C18 N22B C23B 126.8(11) . . ?
C18 N22B H22B 118(4) . . ?
C23B N22B H22B 104(3) . . ?
C24B C23B N22B 107.1(13) . . ?
C24B C23B H23C 110.3 . . ?
N22B C23B H23C 110.3 . . ?
C24B C23B H23D 110.3 . . ?
N22B C23B H23D 110.3 . . ?
H23C C23B H23D 108.6 . . ?
C25B C26B C27B 120.4(19) . . ?
C25B C26B H26B 119.8 . . ?
C27B C26B H26B 119.8 . . ?
C28B C27B C26B 115.8(19) . . ?
C28B C27B H27B 122.1 . . ?
C26B C27B H27B 122.1 . . ?
C25B C24B C23B 127.9(19) . . ?
C25B C24B C29B 114.2(18) . . ?
C23B C24B C29B 118(2) . . ?
C26B C25B C24B 124.5(19) . . ?
C26B C25B H25B 117.8 . . ?
C24B C25B H25B 117.8 . . ?
C28B C29B C24B 117.7(19) . . ?
C28B C29B H29B 121.1 . . ?
C24B C29B H29B 121.1 . . ?
C29B C28B C27B 127(2) . . ?
C29B C28B H28B 116.5 . . ?
C27B C28B H28B 116.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N33 N32 N31 C35 0.3(2) . . . . ?
N33 N32 N31 C36 179.05(17) . . . . ?
N2 N3 N4 C5 0.3(2) . . . . ?
N4 N3 N2 N1 0.0(2) . . . . ?
N31 N32 N33 N34 0.0(2) . . . . ?
N32 N33 N34 C35 -0.3(2) . . . . ?
N3 N2 N1 C5 -0.3(2) . . . . ?
N3 N2 N1 C6 177.17(16) . . . . ?
N3 N4 C5 N1 -0.4(2) . . . . ?
N3 N4 C5 C18 179.87(18) . . . . ?
N2 N1 C5 N4 0.4(2) . . . . ?
C6 N1 C5 N4 -176.57(19) . . . . ?
N2 N1 C5 C18 -179.87(18) . . . . ?
C6 N1 C5 C18 3.1(3) . . . . ?
N33 N34 C35 N31 0.5(2) . . . . ?
N33 N34 C35 C48 -178.35(18) . . . . ?
N32 N31 C35 N34 -0.5(2) . . . . ?
C36 N31 C35 N34 -179.02(19) . . . . ?
N32 N31 C35 C48 178.25(18) . . . . ?
C36 N31 C35 C48 -0.2(3) . . . . ?
C53 N52 C48 C35 -68.9(2) . . . . ?
C53 N52 C48 C49 168.97(16) . . . . ?
N34 C35 C48 N52 -38.2(3) . . . . ?
N31 C35 C48 N52 143.1(2) . . . . ?
N34 C35 C48 C49 83.4(2) . . . . ?
N31 C35 C48 C49 -95.2(2) . . . . ?
C8 N10 C11 C12 -85.1(2) . . . . ?
C17 C12 C11 N10 -10.6(3) . . . . ?
C13 C12 C11 N10 169.79(17) . . . . ?
C35 N31 C36 C37 -127.8(2) . . . . ?
N32 N31 C36 C37 53.8(2) . . . . ?
C13 C12 C17 C16 -0.6(3) . . . . ?
C11 C12 C17 C16 179.78(18) . . . . ?
N31 C36 C37 C38 62.1(2) . . . . ?
C11 N10 C8 O9 -1.5(3) . . . . ?
C11 N10 C8 C7 178.43(17) . . . . ?
C56 C55 C54 C59 -0.6(3) . . . . ?
C56 C55 C54 C53 176.50(18) . . . . ?
C43 C42 C47 C46 0.2(3) . . . . ?
C41 C42 C47 C46 -178.44(18) . . . . ?
C55 C54 C59 C58 -0.2(3) . . . . ?
C53 C54 C59 C58 -177.21(18) . . . . ?
C38 N40 C41 C42 -78.6(2) . . . . ?
C47 C42 C41 N40 -20.3(3) . . . . ?
C43 C42 C41 N40 161.18(18) . . . . ?
C54 C55 C56 C57 0.6(3) . . . . ?
C58 C57 C56 C55 0.2(3) . . . . ?
C5 N1 C6 C7 -132.1(2) . . . . ?
N2 N1 C6 C7 51.1(2) . . . . ?
C56 C57 C58 C59 -0.9(3) . . . . ?
C54 C59 C58 C57 0.9(3) . . . . ?
C47 C42 C43 C44 0.3(3) . . . . ?
C41 C42 C43 C44 178.93(19) . . . . ?
C47 C42 C43 Cl43 179.93(15) . . . . ?
C41 C42 C43 Cl43 -1.4(3) . . . . ?
C41 N40 C38 O39 -3.6(3) . . . . ?
C41 N40 C38 C37 176.18(17) . . . . ?
C36 C37 C38 O39 41.9(2) . . . . ?
C36 C37 C38 N40 -137.89(18) . . . . ?
O9 C8 C7 C6 42.5(2) . . . . ?
N10 C8 C7 C6 -137.47(17) . . . . ?
N1 C6 C7 C8 63.1(2) . . . . ?
C48 N52 C53 C54 -88.7(2) . . . . ?
C55 C54 C53 N52 147.71(19) . . . . ?
C59 C54 C53 N52 -35.3(3) . . . . ?
C42 C47 C46 C45 -0.6(3) . . . . ?
N52 C48 C49 C51 177.31(17) . . . . ?
C35 C48 C49 C51 54.3(2) . . . . ?
N52 C48 C49 C50 -58.1(2) . . . . ?
C35 C48 C49 C50 178.91(18) . . . . ?
C17 C12 C13 C14 1.1(3) . . . . ?
C11 C12 C13 C14 -179.3(2) . . . . ?
C17 C12 C13 Cl13 -179.47(14) . . . . ?
C11 C12 C13 Cl13 0.1(3) . . . . ?
C47 C46 C45 C44 0.5(3) . . . . ?
C12 C13 C14 C15 -1.1(4) . . . . ?
Cl13 C13 C14 C15 179.40(19) . . . . ?
C46 C45 C44 C43 0.0(3) . . . . ?
C42 C43 C44 C45 -0.4(3) . . . . ?
Cl43 C43 C44 C45 179.99(16) . . . . ?
C12 C17 C16 C15 0.3(3) . . . . ?
C13 C14 C15 C16 0.7(4) . . . . ?
C17 C16 C15 C14 -0.3(4) . . . . ?
N4 C5 C18 N22B -101.8(6) . . . . ?
N1 C5 C18 N22B 78.6(6) . . . . ?
N4 C5 C18 N22A -30.8(3) . . . . ?
N1 C5 C18 N22A 149.5(2) . . . . ?
N4 C5 C18 C19 95.1(2) . . . . ?
N1 C5 C18 C19 -84.5(2) . . . . ?
N22B C18 C19 C21 147.7(7) . . . . ?
N22A C18 C19 C21 73.4(2) . . . . ?
C5 C18 C19 C21 -53.3(2) . . . . ?
N22B C18 C19 C20 23.1(7) . . . . ?
N22A C18 C19 C20 -51.2(2) . . . . ?
C5 C18 C19 C20 -177.90(18) . . . . ?
C5 C18 N22A C23A -61.7(3) . . . . ?
C19 C18 N22A C23A 172.60(18) . . . . ?
C18 N22A C23A C24A -87.3(3) . . . . ?
N22A C23A C24A C29A -49.6(3) . . . . ?
N22A C23A C24A C25A 132.7(3) . . . . ?
C29A C24A C25A C26A -0.5(5) . . . . ?
C23A C24A C25A C26A 177.3(3) . . . . ?
C24A C25A C26A C27A 0.0(5) . . . . ?
C25A C26A C27A C28A 0.4(5) . . . . ?
C26A C27A C28A C29A -0.3(5) . . . . ?
C25A C24A C29A C28A 0.7(4) . . . . ?
C23A C24A C29A C28A -177.1(3) . . . . ?
C27A C28A C29A C24A -0.3(4) . . . . ?
C5 C18 N22B C23B 60.0(14) . . . . ?
C19 C18 N22B C23B -141.5(11) . . . . ?
C18 N22B C23B C24B 174.9(13) . . . . ?
C25B C26B C27B C28B -3(3) . . . . ?
N22B C23B C24B C25B 103(2) . . . . ?
N22B C23B C24B C29B -71.8(18) . . . . ?
C27B C26B C25B C24B 1(3) . . . . ?
C23B C24B C25B C26B -176.9(17) . . . . ?
C29B C24B C25B C26B -1(3) . . . . ?
C25B C24B C29B C28B 4(2) . . . . ?
C23B C24B C29B C28B -180.0(17) . . . . ?
C24B C29B C28B C27B -7(3) . . . . ?
C26B C27B C28B C29B 6(3) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ea713_1
_database_code_depnum_ccdc_archive 'CCDC 1842385'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Kurpiewska'
;Jagiellonian University
Poland
;
_audit_update_record             
;
2018-05-09 deposited with the CCDC.	2020-01-07 downloaded from the CCDC.
;

_audit_creation_date             2018-05-09T17:20:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C50 H60 Cl8 N12 O2'
_chemical_formula_moiety         'C50 H60 Cl8 N12 O2'
_chemical_formula_weight         1144.7

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_diffrn_measurement_method       'ω scans'
_symmetry_space_group_name_H-M_alt 'P -1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_cell_setting           triclinic
_space_group_IT_number           2
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3164(4)
_cell_length_b                   15.7661(6)
_cell_length_c                   18.2979(6)
_cell_angle_alpha                68.115(3)
_cell_angle_beta                 89.376(3)
_cell_angle_gamma                87.542(3)
_cell_volume                     2759.08(17)
_cell_measurement_temperature    132(4)
_cell_measurement_reflns_used    10567
_cell_measurement_theta_min      3.0370
_cell_measurement_theta_max      28.1730
_cell_formula_units_Z            2

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1192
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.459
_exptl_absorpt_correction_T_min  0.42804
_exptl_absorpt_correction_T_max  1.00000
_oxdiff_exptl_absorpt_empirical_full_min 0.392
_oxdiff_exptl_absorpt_empirical_full_max 1.870

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      132(4)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.3756
_diffrn_reflns_number            25215
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0518
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.8769
_diffrn_reflns_theta_max         28.6788
_diffrn_measured_fraction_theta_max 0.8790
_diffrn_reflns_theta_full        26.3154
_diffrn_measured_fraction_theta_full 0.9986
_reflns_number_total             12499
_reflns_number_gt                9442
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      'calc '
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         12499
_refine_ls_number_parameters     661
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.131
_refine_ls_wR_factor_gt          0.1131
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.066

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C10 C 1.04536(19) 0.06489(13) -0.28985(12) 0.0226(4) Uani 1 d . . .
C11 C 1.1299(2) -0.02471(13) -0.26313(14) 0.0330(5) Uani 1 d . . .
H11A H 1.1975 -0.0224 -0.301 0.04 Uiso 1 calc R . .
H11B H 1.1691 -0.0375 -0.212 0.04 Uiso 1 calc R . .
C12 C 1.0311(3) -0.09528(15) -0.25935(17) 0.0479(7) Uani 1 d . . .
H12A H 1.074 -0.1505 -0.2611 0.057 Uiso 1 calc R . .
H12B H 0.9806 -0.1111 -0.2114 0.057 Uiso 1 calc R . .
C13 C 0.9454(2) -0.04910(16) -0.33139(17) 0.0426(6) Uani 1 d . . .
H13A H 0.8556 -0.0644 -0.319 0.051 Uiso 1 calc R . .
H13B H 0.9727 -0.0684 -0.3739 0.051 Uiso 1 calc R . .
C14 C 0.9606(2) 0.05428(15) -0.35508(13) 0.0312(5) Uani 1 d . . .
H14A H 0.8766 0.0855 -0.3582 0.037 Uiso 1 calc R . .
H14B H 1.0027 0.0797 -0.4059 0.037 Uiso 1 calc R . .
C15 C 1.12922(18) 0.14652(12) -0.31902(11) 0.0194(4) Uani 1 d . . .
C2 C 0.7611(2) 0.11716(15) 0.00781(12) 0.0287(5) Uani 1 d . . .
C20 C 0.95538(19) 0.27632(14) -0.36405(13) 0.0261(4) Uani 1 d . . .
H20A H 0.8951 0.2286 -0.3577 0.031 Uiso 1 calc R . .
H20B H 0.9492 0.3192 -0.4182 0.031 Uiso 1 calc R . .
C21 C 0.91507(19) 0.32618(13) -0.30969(12) 0.0242(4) Uani 1 d . . .
H21A H 0.822 0.3388 -0.3141 0.029 Uiso 1 calc R . .
H21B H 0.9344 0.2864 -0.2557 0.029 Uiso 1 calc R . .
C22 C 0.98262(19) 0.41571(12) -0.32791(11) 0.0214(4) Uani 1 d . . .
H22A H 1.0748 0.4029 -0.3173 0.026 Uiso 1 calc R . .
H22B H 0.9716 0.4532 -0.3833 0.026 Uiso 1 calc R . .
C23 C 0.92812(18) 0.46754(12) -0.27881(11) 0.0209(4) Uani 1 d . . .
C26 C 0.9607(2) 0.51266(16) -0.16661(13) 0.0308(5) Uani 1 d . . .
H26A H 0.912 0.4701 -0.124 0.037 Uiso 1 calc R . .
H26B H 0.9033 0.5648 -0.1947 0.037 Uiso 1 calc R . .
C27 C 1.07281(19) 0.54423(14) -0.13284(12) 0.0255(4) Uani 1 d . . .
C34 C 0.75354(18) 0.39064(13) 0.47452(11) 0.0219(4) Uani 1 d . . .
C28 C 1.1188(2) 0.63145(15) -0.17025(13) 0.0327(5) Uani 1 d . . .
H28 H 1.0822 0.6701 -0.2179 0.039 Uiso 1 calc R . .
C35 C 0.75663(19) 0.47215(13) 0.48689(11) 0.0240(4) Uani 1 d . . .
H35 H 0.813 0.5172 0.4587 0.029 Uiso 1 calc R . .
C29 C 1.2190(2) 0.66112(17) -0.13693(16) 0.0417(6) Uani 1 d . . .
H29 H 1.2482 0.72 -0.1617 0.05 Uiso 1 calc R . .
C3 C 0.7543(2) 0.03408(15) -0.00110(12) 0.0308(5) Uani 1 d . . .
H3 H 0.6949 -0.0084 0.0274 0.037 Uiso 1 calc R . .
C36 C 0.6735(2) 0.48468(14) 0.54252(11) 0.0248(4) Uani 1 d . . .
H36 H 0.6748 0.5389 0.5516 0.03 Uiso 1 calc R . .
C30 C 1.2754(2) 0.60323(19) -0.06712(15) 0.0438(6) Uani 1 d . . .
H30 H 1.3424 0.6231 -0.0447 0.053 Uiso 1 calc R . .
C37 C 0.6701(2) 0.32311(14) 0.51583(12) 0.0256(4) Uani 1 d . . .
H37 H 0.6691 0.269 0.5067 0.031 Uiso 1 calc R . .
C31 C 1.2324(2) 0.5162(2) -0.03074(14) 0.0454(6) Uani 1 d . . .
H31 H 1.2715 0.4768 0.0158 0.054 Uiso 1 calc R . .
C38 C 0.5881(2) 0.33713(14) 0.57107(12) 0.0264(4) Uani 1 d . . .
H38 H 0.532 0.2918 0.5993 0.032 Uiso 1 calc R . .
C32 C 1.1309(2) 0.48713(16) -0.06317(13) 0.0350(5) Uani 1 d . . .
H32 H 1.1015 0.4284 -0.0378 0.042 Uiso 1 calc R . .
C39 C 0.58847(18) 0.41838(14) 0.58493(11) 0.0235(4) Uani 1 d . . .
C40 C 0.49704(19) 0.43528(15) 0.64370(11) 0.0274(4) Uani 1 d . . .
H40A H 0.4697 0.4995 0.6247 0.033 Uiso 1 calc R . .
H40B H 0.4204 0.4 0.6489 0.033 Uiso 1 calc R . .
C42 C 0.47453(18) 0.41791(13) 0.78379(11) 0.0203(4) Uani 1 d . . .
C43 C 0.39821(19) 0.51076(13) 0.76275(12) 0.0248(4) Uani 1 d . . .
H43A H 0.3645 0.5324 0.7093 0.03 Uiso 1 calc R . .
H43B H 0.3269 0.5062 0.7988 0.03 Uiso 1 calc R . .
C44 C 0.5001(2) 0.57296(14) 0.77130(13) 0.0307(5) Uani 1 d . . .
H44A H 0.4603 0.6281 0.775 0.037 Uiso 1 calc R . .
H44B H 0.5594 0.5899 0.7271 0.037 Uiso 1 calc R . .
C45 C 0.5700(2) 0.51489(14) 0.84765(13) 0.0307(5) Uani 1 d . . .
H45A H 0.5284 0.5236 0.8923 0.037 Uiso 1 calc R . .
H45B H 0.6599 0.5312 0.846 0.037 Uiso 1 calc R . .
C4 C 0.8380(2) 0.01549(15) -0.05338(12) 0.0291(5) Uani 1 d . . .
H4 H 0.8337 -0.0399 -0.0601 0.035 Uiso 1 calc R . .
C46 C 0.5611(2) 0.41471(14) 0.85415(12) 0.0245(4) Uani 1 d . . .
H46A H 0.5224 0.378 0.9038 0.029 Uiso 1 calc R . .
H46B H 0.6468 0.3885 0.8509 0.029 Uiso 1 calc R . .
C47 C 0.38318(18) 0.34058(13) 0.80484(11) 0.0193(4) Uani 1 d . . .
C52 C 0.54657(19) 0.20434(14) 0.85222(12) 0.0257(4) Uani 1 d . . .
H52A H 0.545 0.1598 0.9058 0.031 Uiso 1 calc R . .
H52B H 0.6096 0.2491 0.8503 0.031 Uiso 1 calc R . .
C53 C 0.59014(19) 0.15590(13) 0.79739(12) 0.0240(4) Uani 1 d . . .
H53A H 0.5711 0.1961 0.7435 0.029 Uiso 1 calc R . .
H53B H 0.6834 0.1445 0.8022 0.029 Uiso 1 calc R . .
C54 C 0.52545(19) 0.06561(13) 0.81423(12) 0.0239(4) Uani 1 d . . .
H54A H 0.541 0.0257 0.8687 0.029 Uiso 1 calc R . .
H54B H 0.4325 0.0767 0.8063 0.029 Uiso 1 calc R . .
C55 C 0.57875(19) 0.01958(13) 0.76031(12) 0.0237(4) Uani 1 d . . .
C5 C 0.8503(2) 0.18015(15) -0.03295(13) 0.0322(5) Uani 1 d . . .
H5 H 0.8544 0.2354 -0.0258 0.039 Uiso 1 calc R . .
C58 C 0.5410(2) -0.00856(19) 0.63904(15) 0.0407(6) Uani 1 d . . .
H58A H 0.6121 -0.0536 0.6583 0.049 Uiso 1 calc R . .
H58B H 0.5713 0.0415 0.5934 0.049 Uiso 1 calc R . .
C59 C 0.4300(2) -0.05148(15) 0.61508(13) 0.0296(5) Uani 1 d . . .
C60 C 0.4062(2) -0.14327(16) 0.65524(15) 0.0392(6) Uani 1 d . . .
H60 H 0.46 -0.1785 0.6969 0.047 Uiso 1 calc R . .
C61 C 0.3034(3) -0.18291(17) 0.63395(16) 0.0441(6) Uani 1 d . . .
H61 H 0.2889 -0.2446 0.6611 0.053 Uiso 1 calc R . .
C62 C 0.2225(2) -0.13149(18) 0.57277(16) 0.0421(6) Uani 1 d . . .
H62 H 0.1535 -0.1582 0.5584 0.05 Uiso 1 calc R . .
C63 C 0.2445(2) -0.04030(18) 0.53300(14) 0.0402(6) Uani 1 d . . .
H63 H 0.1894 -0.0051 0.492 0.048 Uiso 1 calc R . .
C64 C 0.3481(2) -0.00046(16) 0.55363(14) 0.0348(5) Uani 1 d . . .
H64 H 0.3627 0.0611 0.5259 0.042 Uiso 1 calc R . .
C65 C 0.2832(2) 0.21868(15) 0.10737(13) 0.0315(5) Uani 1 d . . .
H65 H 0.2794 0.1552 0.1445 0.038 Uiso 1 calc R . .
C6 C 0.9338(2) 0.16013(15) -0.08473(12) 0.0304(5) Uani 1 d . . .
H6 H 0.9943 0.2023 -0.1123 0.036 Uiso 1 calc R . .
C69 C 0.2338(2) 0.28576(14) 0.39653(13) 0.0305(5) Uani 1 d . . .
H69 H 0.2004 0.3492 0.3806 0.037 Uiso 1 calc R . .
C7 C 0.92830(19) 0.07774(15) -0.09603(11) 0.0272(4) Uani 1 d . . .
C8 C 1.0195(2) 0.05484(15) -0.15162(12) 0.0302(5) Uani 1 d . . .
H8A H 1.0973 0.0893 -0.1579 0.036 Uiso 1 calc R . .
H8B H 1.0447 -0.0098 -0.1294 0.036 Uiso 1 calc R . .
Cl1 Cl 0.65423(6) 0.14309(4) 0.07210(3) 0.04171(15) Uani 1 d . . .
Cl33 Cl 0.85691(5) 0.37423(4) 0.40403(3) 0.03162(13) Uani 1 d . . .
Cl68 Cl 0.14128(6) 0.27918(4) 0.11751(4) 0.04485(16) Uani 1 d . . .
Cl67 Cl 0.29530(7) 0.21867(5) 0.01177(4) 0.05003(18) Uani 1 d . . .
Cl66 Cl 0.41907(7) 0.26737(5) 0.13082(5) 0.0555(2) Uani 1 d . . .
Cl71 Cl 0.23444(7) 0.25508(4) 0.31378(4) 0.04653(17) Uani 1 d . . .
Cl70 Cl 0.39056(6) 0.27792(4) 0.43547(3) 0.04006(15) Uani 1 d . . .
Cl72 Cl 0.13056(6) 0.21490(5) 0.46953(4) 0.04733(17) Uani 1 d . . .
N16 N 1.25752(16) 0.14434(11) -0.32062(10) 0.0241(4) Uani 1 d . . .
N17 N 1.29292(17) 0.23297(12) -0.35233(11) 0.0283(4) Uani 1 d . . .
N18 N 1.19131(17) 0.28794(11) -0.37022(10) 0.0264(4) Uani 1 d . . .
N19 N 1.08717(15) 0.23530(10) -0.34924(9) 0.0210(3) Uani 1 d . . .
N25 N 1.00418(17) 0.46799(12) -0.22048(10) 0.0247(4) Uani 1 d . . .
N41 N 0.56011(16) 0.40943(11) 0.72130(9) 0.0213(3) Uani 1 d . . .
N48 N 0.25499(15) 0.34836(11) 0.79912(10) 0.0229(3) Uani 1 d . . .
N49 N 0.21247(16) 0.26135(12) 0.82351(10) 0.0265(4) Uani 1 d . . .
N50 N 0.30942(16) 0.20222(11) 0.84401(10) 0.0254(4) Uani 1 d . . .
N51 N 0.41806(15) 0.25063(11) 0.83232(9) 0.0210(3) Uani 1 d . . .
N57 N 0.50230(18) 0.02596(13) 0.70045(11) 0.0308(4) Uani 1 d . . .
N9 N 0.95839(16) 0.07643(12) -0.22894(10) 0.0226(4) Uani 1 d . . .
O24 O 0.81918(13) 0.50629(9) -0.29211(8) 0.0267(3) Uani 1 d . . .
056 O 0.68814(14) -0.01893(10) 0.77122(9) 0.0308(3) Uani 1 d . . .
H57 H 0.431(3) 0.0570(16) 0.6941(14) 0.037 Uiso 1 d . . .
H25 H 1.075(3) 0.4370(16) -0.2124(14) 0.037 Uiso 1 d . . .
H41 H 0.625(3) 0.4406(17) 0.7181(14) 0.037 Uiso 1 d . . .
H9 H 0.895(3) 0.0459(16) -0.2258(14) 0.037 Uiso 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C10 N9 1.482(2) . ?
C10 C15 1.504(3) . ?
C10 C11 1.544(3) . ?
C10 C14 1.549(3) . ?
C11 C12 1.523(3) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 C13 1.518(4) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C13 C14 1.537(3) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C15 N16 1.323(2) . ?
C15 N19 1.353(2) . ?
C2 C5 1.379(3) . ?
C2 C3 1.384(3) . ?
C2 Cl1 1.748(2) . ?
C20 N19 1.464(2) . ?
C20 C21 1.525(3) . ?
C20 H20A 0.97 . ?
C20 H20B 0.97 . ?
C21 C22 1.522(3) . ?
C21 H21A 0.97 . ?
C21 H21B 0.97 . ?
C22 C23 1.513(2) . ?
C22 H22A 0.97 . ?
C22 H22B 0.97 . ?
C23 O24 1.238(2) . ?
C23 N25 1.334(3) . ?
C26 N25 1.466(2) . ?
C26 C27 1.504(3) . ?
C26 H26A 0.97 . ?
C26 H26B 0.97 . ?
C27 C32 1.382(3) . ?
C27 C28 1.390(3) . ?
C34 C37 1.382(3) . ?
C34 C35 1.387(3) . ?
C34 Cl33 1.7501(19) . ?
C28 C29 1.388(3) . ?
C28 H28 0.93 . ?
C35 C36 1.388(3) . ?
C35 H35 0.93 . ?
C29 C30 1.380(4) . ?
C29 H29 0.93 . ?
C3 C4 1.384(3) . ?
C3 H3 0.93 . ?
C36 C39 1.387(3) . ?
C36 H36 0.93 . ?
C30 C31 1.374(4) . ?
C30 H30 0.93 . ?
C37 C38 1.385(3) . ?
C37 H37 0.93 . ?
C31 C32 1.384(3) . ?
C31 H31 0.93 . ?
C38 C39 1.396(3) . ?
C38 H38 0.93 . ?
C32 H32 0.93 . ?
C39 C40 1.512(3) . ?
C40 N41 1.474(2) . ?
C40 H40A 0.97 . ?
C40 H40B 0.97 . ?
C42 N41 1.479(2) . ?
C42 C47 1.504(3) . ?
C42 C43 1.549(3) . ?
C42 C46 1.559(3) . ?
C43 C44 1.516(3) . ?
C43 H43A 0.97 . ?
C43 H43B 0.97 . ?
C44 C45 1.524(3) . ?
C44 H44A 0.97 . ?
C44 H44B 0.97 . ?
C45 C46 1.546(3) . ?
C45 H45A 0.97 . ?
C45 H45B 0.97 . ?
C4 C7 1.390(3) . ?
C4 H4 0.93 . ?
C46 H46A 0.97 . ?
C46 H46B 0.97 . ?
C47 N48 1.325(2) . ?
C47 N51 1.350(2) . ?
C52 N51 1.467(2) . ?
C52 C53 1.524(3) . ?
C52 H52A 0.97 . ?
C52 H52B 0.97 . ?
C53 C54 1.522(3) . ?
C53 H53A 0.97 . ?
C53 H53B 0.97 . ?
C54 C55 1.513(3) . ?
C54 H54A 0.97 . ?
C54 H54B 0.97 . ?
C55 056 1.240(2) . ?
C55 N57 1.327(3) . ?
C5 C6 1.386(3) . ?
C5 H5 0.93 . ?
C58 N57 1.465(3) . ?
C58 C59 1.503(3) . ?
C58 H58A 0.97 . ?
C58 H58B 0.97 . ?
C59 C64 1.383(3) . ?
C59 C60 1.388(3) . ?
C60 C61 1.384(4) . ?
C60 H60 0.93 . ?
C61 C62 1.376(4) . ?
C61 H61 0.93 . ?
C62 C63 1.376(4) . ?
C62 H62 0.93 . ?
C63 C64 1.387(3) . ?
C63 H63 0.93 . ?
C64 H64 0.93 . ?
C65 Cl67 1.753(2) . ?
C65 Cl66 1.758(2) . ?
C65 Cl68 1.759(2) . ?
C65 H65 0.98 . ?
C6 C7 1.393(3) . ?
C6 H6 0.93 . ?
C69 Cl71 1.753(2) . ?
C69 Cl70 1.755(2) . ?
C69 Cl72 1.768(2) . ?
C69 H69 0.98 . ?
C7 C8 1.508(3) . ?
C8 N9 1.468(3) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
N16 N17 1.363(2) . ?
N17 N18 1.294(2) . ?
N18 N19 1.349(2) . ?
N25 H25 0.85(3) . ?
N41 H41 0.83(3) . ?
N48 N49 1.366(2) . ?
N49 N50 1.295(2) . ?
N50 N51 1.353(2) . ?
N57 H57 0.85(3) . ?
N9 H9 0.82(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N9 C10 C15 107.38(15) . . ?
N9 C10 C11 115.39(16) . . ?
C15 C10 C11 110.52(16) . . ?
N9 C10 C14 108.44(16) . . ?
C15 C10 C14 113.63(16) . . ?
C11 C10 C14 101.58(16) . . ?
C12 C11 C10 102.13(18) . . ?
C12 C11 H11A 111.3 . . ?
C10 C11 H11A 111.3 . . ?
C12 C11 H11B 111.3 . . ?
C10 C11 H11B 111.3 . . ?
H11A C11 H11B 109.2 . . ?
C13 C12 C11 104.78(19) . . ?
C13 C12 H12A 110.8 . . ?
C11 C12 H12A 110.8 . . ?
C13 C12 H12B 110.8 . . ?
C11 C12 H12B 110.8 . . ?
H12A C12 H12B 108.9 . . ?
C12 C13 C14 106.05(19) . . ?
C12 C13 H13A 110.5 . . ?
C14 C13 H13A 110.5 . . ?
C12 C13 H13B 110.5 . . ?
C14 C13 H13B 110.5 . . ?
H13A C13 H13B 108.7 . . ?
C13 C14 C10 105.87(19) . . ?
C13 C14 H14A 110.6 . . ?
C10 C14 H14A 110.6 . . ?
C13 C14 H14B 110.6 . . ?
C10 C14 H14B 110.6 . . ?
H14A C14 H14B 108.7 . . ?
N16 C15 N19 107.63(17) . . ?
N16 C15 C10 126.12(17) . . ?
N19 C15 C10 126.24(17) . . ?
C5 C2 C3 121.44(19) . . ?
C5 C2 Cl1 119.14(17) . . ?
C3 C2 Cl1 119.42(16) . . ?
N19 C20 C21 113.60(16) . . ?
N19 C20 H20A 108.8 . . ?
C21 C20 H20A 108.8 . . ?
N19 C20 H20B 108.8 . . ?
C21 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C22 C21 C20 113.37(16) . . ?
C22 C21 H21A 108.9 . . ?
C20 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
C20 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C23 C22 C21 111.19(15) . . ?
C23 C22 H22A 109.4 . . ?
C21 C22 H22A 109.4 . . ?
C23 C22 H22B 109.4 . . ?
C21 C22 H22B 109.4 . . ?
H22A C22 H22B 108 . . ?
O24 C23 N25 122.60(17) . . ?
O24 C23 C22 121.55(18) . . ?
N25 C23 C22 115.85(16) . . ?
N25 C26 C27 111.85(16) . . ?
N25 C26 H26A 109.2 . . ?
C27 C26 H26A 109.2 . . ?
N25 C26 H26B 109.2 . . ?
C27 C26 H26B 109.2 . . ?
H26A C26 H26B 107.9 . . ?
C32 C27 C28 118.8(2) . . ?
C32 C27 C26 120.4(2) . . ?
C28 C27 C26 120.9(2) . . ?
C37 C34 C35 121.54(18) . . ?
C37 C34 Cl33 119.65(15) . . ?
C35 C34 Cl33 118.80(15) . . ?
C29 C28 C27 120.4(2) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C34 C35 C36 118.28(18) . . ?
C34 C35 H35 120.9 . . ?
C36 C35 H35 120.9 . . ?
C30 C29 C28 120.0(2) . . ?
C30 C29 H29 120 . . ?
C28 C29 H29 120 . . ?
C2 C3 C4 118.59(19) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C39 C36 C35 121.65(18) . . ?
C39 C36 H36 119.2 . . ?
C35 C36 H36 119.2 . . ?
C31 C30 C29 119.9(2) . . ?
C31 C30 H30 120 . . ?
C29 C30 H30 120 . . ?
C34 C37 C38 119.15(18) . . ?
C34 C37 H37 120.4 . . ?
C38 C37 H37 120.4 . . ?
C30 C31 C32 120.1(2) . . ?
C30 C31 H31 120 . . ?
C32 C31 H31 120 . . ?
C37 C38 C39 120.82(18) . . ?
C37 C38 H38 119.6 . . ?
C39 C38 H38 119.6 . . ?
C27 C32 C31 120.8(2) . . ?
C27 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C36 C39 C38 118.55(18) . . ?
C36 C39 C40 120.20(18) . . ?
C38 C39 C40 121.24(18) . . ?
N41 C40 C39 111.02(16) . . ?
N41 C40 H40A 109.4 . . ?
C39 C40 H40A 109.4 . . ?
N41 C40 H40B 109.4 . . ?
C39 C40 H40B 109.4 . . ?
H40A C40 H40B 108 . . ?
N41 C42 C47 106.57(15) . . ?
N41 C42 C43 115.59(15) . . ?
C47 C42 C43 110.69(16) . . ?
N41 C42 C46 108.33(15) . . ?
C47 C42 C46 113.39(15) . . ?
C43 C42 C46 102.44(15) . . ?
C44 C43 C42 102.78(16) . . ?
C44 C43 H43A 111.2 . . ?
C42 C43 H43A 111.2 . . ?
C44 C43 H43B 111.2 . . ?
C42 C43 H43B 111.2 . . ?
H43A C43 H43B 109.1 . . ?
C43 C44 C45 103.58(16) . . ?
C43 C44 H44A 111 . . ?
C45 C44 H44A 111 . . ?
C43 C44 H44B 111 . . ?
C45 C44 H44B 111 . . ?
H44A C44 H44B 109 . . ?
C44 C45 C46 105.70(16) . . ?
C44 C45 H45A 110.6 . . ?
C46 C45 H45A 110.6 . . ?
C44 C45 H45B 110.6 . . ?
C46 C45 H45B 110.6 . . ?
H45A C45 H45B 108.7 . . ?
C3 C4 C7 121.5(2) . . ?
C3 C4 H4 119.2 . . ?
C7 C4 H4 119.2 . . ?
C45 C46 C42 106.14(16) . . ?
C45 C46 H46A 110.5 . . ?
C42 C46 H46A 110.5 . . ?
C45 C46 H46B 110.5 . . ?
C42 C46 H46B 110.5 . . ?
H46A C46 H46B 108.7 . . ?
N48 C47 N51 107.90(17) . . ?
N48 C47 C42 126.36(17) . . ?
N51 C47 C42 125.74(16) . . ?
N51 C52 C53 113.37(16) . . ?
N51 C52 H52A 108.9 . . ?
C53 C52 H52A 108.9 . . ?
N51 C52 H52B 108.9 . . ?
C53 C52 H52B 108.9 . . ?
H52A C52 H52B 107.7 . . ?
C54 C53 C52 113.52(16) . . ?
C54 C53 H53A 108.9 . . ?
C52 C53 H53A 108.9 . . ?
C54 C53 H53B 108.9 . . ?
C52 C53 H53B 108.9 . . ?
H53A C53 H53B 107.7 . . ?
C55 C54 C53 110.29(15) . . ?
C55 C54 H54A 109.6 . . ?
C53 C54 H54A 109.6 . . ?
C55 C54 H54B 109.6 . . ?
C53 C54 H54B 109.6 . . ?
H54A C54 H54B 108.1 . . ?
056 C55 N57 123.32(18) . . ?
056 C55 C54 121.24(19) . . ?
N57 C55 C54 115.42(17) . . ?
C2 C5 C6 119.2(2) . . ?
C2 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
N57 C58 C59 111.40(17) . . ?
N57 C58 H58A 109.3 . . ?
C59 C58 H58A 109.3 . . ?
N57 C58 H58B 109.3 . . ?
C59 C58 H58B 109.3 . . ?
H58A C58 H58B 108 . . ?
C64 C59 C60 118.5(2) . . ?
C64 C59 C58 121.0(2) . . ?
C60 C59 C58 120.5(2) . . ?
C61 C60 C59 120.7(2) . . ?
C61 C60 H60 119.6 . . ?
C59 C60 H60 119.6 . . ?
C62 C61 C60 120.3(2) . . ?
C62 C61 H61 119.9 . . ?
C60 C61 H61 119.9 . . ?
C61 C62 C63 119.5(2) . . ?
C61 C62 H62 120.3 . . ?
C63 C62 H62 120.3 . . ?
C62 C63 C64 120.5(2) . . ?
C62 C63 H63 119.8 . . ?
C64 C63 H63 119.8 . . ?
C59 C64 C63 120.5(2) . . ?
C59 C64 H64 119.7 . . ?
C63 C64 H64 119.7 . . ?
Cl67 C65 Cl66 110.88(12) . . ?
Cl67 C65 Cl68 110.84(13) . . ?
Cl66 C65 Cl68 109.46(12) . . ?
Cl67 C65 H65 108.5 . . ?
Cl66 C65 H65 108.5 . . ?
Cl68 C65 H65 108.5 . . ?
C5 C6 C7 120.90(19) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
Cl71 C69 Cl70 111.52(12) . . ?
Cl71 C69 Cl72 109.99(12) . . ?
Cl70 C69 Cl72 109.74(12) . . ?
Cl71 C69 H69 108.5 . . ?
Cl70 C69 H69 108.5 . . ?
Cl72 C69 H69 108.5 . . ?
C4 C7 C6 118.37(19) . . ?
C4 C7 C8 120.24(19) . . ?
C6 C7 C8 121.37(18) . . ?
N9 C8 C7 111.20(16) . . ?
N9 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
N9 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108 . . ?
C15 N16 N17 106.59(16) . . ?
N18 N17 N16 110.45(15) . . ?
N17 N18 N19 106.75(15) . . ?
N18 N19 C15 108.56(15) . . ?
N18 N19 C20 120.84(15) . . ?
C15 N19 C20 130.52(16) . . ?
C23 N25 C26 121.26(17) . . ?
C23 N25 H25 118.0(16) . . ?
C26 N25 H25 120.4(16) . . ?
C40 N41 C42 114.55(15) . . ?
C40 N41 H41 110.5(17) . . ?
C42 N41 H41 108.3(16) . . ?
C47 N48 N49 106.33(16) . . ?
N50 N49 N48 110.60(15) . . ?
N49 N50 N51 106.59(15) . . ?
C47 N51 N50 108.57(15) . . ?
C47 N51 C52 130.37(16) . . ?
N50 N51 C52 121.00(15) . . ?
C55 N57 C58 123.27(18) . . ?
C55 N57 H57 118.8(16) . . ?
C58 N57 H57 117.6(16) . . ?
C8 N9 C10 114.89(16) . . ?
C8 N9 H9 111.6(17) . . ?
C10 N9 H9 108.0(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N9 C10 C11 C12 73.8(2) . . . . ?
C15 C10 C11 C12 -164.15(18) . . . . ?
C14 C10 C11 C12 -43.3(2) . . . . ?
C10 C11 C12 C13 40.7(2) . . . . ?
C11 C12 C13 C14 -21.7(2) . . . . ?
C12 C13 C14 C10 -5.7(2) . . . . ?
N9 C10 C14 C13 -91.85(18) . . . . ?
C15 C10 C14 C13 148.83(16) . . . . ?
C11 C10 C14 C13 30.1(2) . . . . ?
N9 C10 C15 N16 125.13(19) . . . . ?
C11 C10 C15 N16 -1.5(3) . . . . ?
C14 C10 C15 N16 -115.0(2) . . . . ?
N9 C10 C15 N19 -55.7(2) . . . . ?
C11 C10 C15 N19 177.60(18) . . . . ?
C14 C10 C15 N19 64.2(2) . . . . ?
N19 C20 C21 C22 71.9(2) . . . . ?
C20 C21 C22 C23 173.44(16) . . . . ?
C21 C22 C23 O24 -72.6(2) . . . . ?
C21 C22 C23 N25 106.9(2) . . . . ?
N25 C26 C27 C32 -90.4(2) . . . . ?
N25 C26 C27 C28 90.5(2) . . . . ?
C32 C27 C28 C29 -1.6(3) . . . . ?
C26 C27 C28 C29 177.46(18) . . . . ?
C37 C34 C35 C36 0.2(3) . . . . ?
Cl33 C34 C35 C36 179.50(15) . . . . ?
C27 C28 C29 C30 1.4(3) . . . . ?
C5 C2 C3 C4 -1.2(3) . . . . ?
Cl1 C2 C3 C4 178.77(17) . . . . ?
C34 C35 C36 C39 -0.3(3) . . . . ?
C28 C29 C30 C31 0.1(4) . . . . ?
C35 C34 C37 C38 -0.2(3) . . . . ?
Cl33 C34 C37 C38 -179.53(15) . . . . ?
C29 C30 C31 C32 -1.3(4) . . . . ?
C34 C37 C38 C39 0.3(3) . . . . ?
C28 C27 C32 C31 0.5(3) . . . . ?
C26 C27 C32 C31 -178.6(2) . . . . ?
C30 C31 C32 C27 1.0(4) . . . . ?
C35 C36 C39 C38 0.4(3) . . . . ?
C35 C36 C39 C40 -178.56(18) . . . . ?
C37 C38 C39 C36 -0.4(3) . . . . ?
C37 C38 C39 C40 178.53(19) . . . . ?
C36 C39 C40 N41 -86.4(2) . . . . ?
C38 C39 C40 N41 94.7(2) . . . . ?
N41 C42 C43 C44 -77.51(19) . . . . ?
C47 C42 C43 C44 161.23(16) . . . . ?
C46 C42 C43 C44 40.05(18) . . . . ?
C42 C43 C44 C45 -43.85(19) . . . . ?
C43 C44 C45 C46 30.1(2) . . . . ?
C2 C3 C4 C7 0.6(3) . . . . ?
C44 C45 C46 C42 -4.9(2) . . . . ?
N41 C42 C46 C45 101.20(17) . . . . ?
C47 C42 C46 C45 -140.73(16) . . . . ?
C43 C42 C46 C45 -21.42(19) . . . . ?
N41 C42 C47 N48 -119.85(19) . . . . ?
C43 C42 C47 N48 6.6(3) . . . . ?
C46 C42 C47 N48 121.1(2) . . . . ?
N41 C42 C47 N51 59.5(2) . . . . ?
C43 C42 C47 N51 -174.08(17) . . . . ?
C46 C42 C47 N51 -59.6(2) . . . . ?
N51 C52 C53 C54 -77.0(2) . . . . ?
C52 C53 C54 C55 -177.08(16) . . . . ?
C53 C54 C55 056 75.0(2) . . . . ?
C53 C54 C55 N57 -103.1(2) . . . . ?
C3 C2 C5 C6 0.8(3) . . . . ?
Cl1 C2 C5 C6 -179.13(17) . . . . ?
N57 C58 C59 C64 91.4(3) . . . . ?
N57 C58 C59 C60 -87.6(3) . . . . ?
C64 C59 C60 C61 0.4(3) . . . . ?
C58 C59 C60 C61 179.3(2) . . . . ?
C59 C60 C61 C62 -0.4(4) . . . . ?
C60 C61 C62 C63 -0.1(4) . . . . ?
C61 C62 C63 C64 0.7(3) . . . . ?
C60 C59 C64 C63 0.3(3) . . . . ?
C58 C59 C64 C63 -178.73(19) . . . . ?
C62 C63 C64 C59 -0.8(3) . . . . ?
C2 C5 C6 C7 0.2(3) . . . . ?
C3 C4 C7 C6 0.4(3) . . . . ?
C3 C4 C7 C8 179.07(19) . . . . ?
C5 C6 C7 C4 -0.8(3) . . . . ?
C5 C6 C7 C8 -179.4(2) . . . . ?
C4 C7 C8 N9 84.4(2) . . . . ?
C6 C7 C8 N9 -96.9(2) . . . . ?
N19 C15 N16 N17 -0.1(2) . . . . ?
C10 C15 N16 N17 179.16(17) . . . . ?
C15 N16 N17 N18 -0.4(2) . . . . ?
N16 N17 N18 N19 0.8(2) . . . . ?
N17 N18 N19 C15 -0.8(2) . . . . ?
N17 N18 N19 C20 -177.89(17) . . . . ?
N16 C15 N19 N18 0.6(2) . . . . ?
C10 C15 N19 N18 -178.70(17) . . . . ?
N16 C15 N19 C20 177.25(18) . . . . ?
C10 C15 N19 C20 -2.0(3) . . . . ?
C21 C20 N19 N18 -72.9(2) . . . . ?
C21 C20 N19 C15 110.8(2) . . . . ?
O24 C23 N25 C26 1.9(3) . . . . ?
C22 C23 N25 C26 -177.54(17) . . . . ?
C27 C26 N25 C23 -153.04(19) . . . . ?
C39 C40 N41 C42 -176.07(16) . . . . ?
C47 C42 N41 C40 73.0(2) . . . . ?
C43 C42 N41 C40 -50.4(2) . . . . ?
C46 C42 N41 C40 -164.67(16) . . . . ?
N51 C47 N48 N49 -0.1(2) . . . . ?
C42 C47 N48 N49 179.29(17) . . . . ?
C47 N48 N49 N50 0.5(2) . . . . ?
N48 N49 N50 N51 -0.6(2) . . . . ?
N48 C47 N51 N50 -0.3(2) . . . . ?
C42 C47 N51 N50 -179.68(17) . . . . ?
N48 C47 N51 C52 -177.37(18) . . . . ?
C42 C47 N51 C52 3.2(3) . . . . ?
N49 N50 N51 C47 0.5(2) . . . . ?
N49 N50 N51 C52 177.98(16) . . . . ?
C53 C52 N51 C47 -112.8(2) . . . . ?
C53 C52 N51 N50 70.4(2) . . . . ?
056 C55 N57 C58 -2.5(3) . . . . ?
C54 C55 N57 C58 175.54(19) . . . . ?
C59 C58 N57 C55 141.2(2) . . . . ?
C7 C8 N9 C10 174.11(17) . . . . ?
C15 C10 N9 C8 -77.7(2) . . . . ?
C11 C10 N9 C8 46.0(2) . . . . ?
C14 C10 N9 C8 159.14(17) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mph159_2
_database_code_depnum_ccdc_archive 'CCDC 1548703'
_audit_update_record             
;
2017-05-08 deposited with the CCDC.	2020-01-07 downloaded from the CCDC.
;

_audit_creation_date             2017-05-05T23:09:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C22 H31 N7 O'
_chemical_formula_moiety         'C22 H31 N7 O'
_chemical_formula_weight         409.54

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.8856(6)
_cell_length_b                   10.4180(5)
_cell_length_c                   42.5525(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4382.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    1042
_cell_measurement_theta_min      3.184
_cell_measurement_theta_max      20.995

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_F_000             1760

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.2818
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.997

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_ambient_temperature      130(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0587955
_diffrn_orient_matrix_ub_12      -0.0074284
_diffrn_orient_matrix_ub_13      0.0093798
_diffrn_orient_matrix_ub_21      0.0411549
_diffrn_orient_matrix_ub_22      -0.0080163
_diffrn_orient_matrix_ub_23      0.0135211
_diffrn_orient_matrix_ub_31      -0.0015678
_diffrn_orient_matrix_ub_32      0.0671773
_diffrn_orient_matrix_ub_33      0.0026411
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.1206
_diffrn_reflns_av_unetI/netI     0.2083
_diffrn_reflns_number            13478
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_theta_min         2.998
_diffrn_reflns_theta_max         28.569
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.9
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.9
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.9
_reflns_Friedel_coverage         0
_reflns_number_total             5024
_reflns_number_gt                2043
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0671P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5024
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2098
_refine_ls_R_factor_gt           0.0836
_refine_ls_wR_factor_ref         0.2206
_refine_ls_wR_factor_gt          0.1581
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.981
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.069

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O18 O 0.2984(3) 0.0246(2) 0.11883(6) 0.0333(7) Uani 1 1 d . . . . .
N19 N 0.2059(3) 0.2227(3) 0.11126(7) 0.0276(8) Uani 1 1 d . . . . .
N5 N -0.0693(3) 0.2571(3) 0.07358(7) 0.0302(8) Uani 1 1 d . . . . .
N2 N -0.1068(4) 0.0671(3) 0.09241(7) 0.0349(8) Uani 1 1 d . . . . .
N4 N -0.1733(4) 0.2057(3) 0.05689(8) 0.0392(9) Uani 1 1 d . . . . .
N12 N 0.4421(3) 0.3078(3) 0.08692(6) 0.0293(8) Uani 1 1 d . . . . .
H12 H 0.4363 0.3891 0.0924 0.035 Uiso 1 1 calc R U . . .
N24 N 0.2240(4) 0.3006(3) 0.21840(8) 0.0466(10) Uani 1 1 d . . . . .
H24 H 0.285 0.3362 0.2307 0.056 Uiso 1 1 calc R U . . .
N3 N -0.1945(4) 0.0919(3) 0.06844(8) 0.0402(9) Uani 1 1 d . . . . .
C17 C 0.3122(4) 0.1408(3) 0.11333(8) 0.0267(9) Uani 1 1 d . . . . .
C13 C 0.4494(4) 0.2034(3) 0.10952(8) 0.0281(9) Uani 1 1 d . . . . .
H13 H 0.5154 0.1379 0.1018 0.034 Uiso 1 1 calc R U . . .
C29 C -0.0199(5) 0.0612(4) 0.20086(10) 0.0421(11) Uani 1 1 d . . . . .
H29 H -0.078 0.0423 0.1837 0.051 Uiso 1 1 calc R U . . .
C15 C 0.4740(5) 0.1633(3) 0.16890(9) 0.0410(11) Uani 1 1 d . . . . .
H15A H 0.523 0.083 0.1651 0.062 Uiso 1 1 calc R U . . .
H15B H 0.377 0.1454 0.1705 0.062 Uiso 1 1 calc R U . . .
H15C H 0.5059 0.2019 0.1885 0.062 Uiso 1 1 calc R U . . .
C7 C 0.0206(4) 0.4030(3) 0.03297(8) 0.0350(10) Uani 1 1 d . . . . .
H7A H -0.0465 0.3618 0.019 0.042 Uiso 1 1 calc R U . . .
H7B H 0.0229 0.4955 0.0277 0.042 Uiso 1 1 calc R U . . .
C14 C 0.4994(4) 0.2564(3) 0.14163(8) 0.0304(9) Uani 1 1 d . . . . .
H14 H 0.4498 0.3381 0.1461 0.036 Uiso 1 1 calc R U . . .
C1 C -0.0297(4) 0.1705(3) 0.09516(9) 0.0286(9) Uani 1 1 d . . . . .
C10 C 0.4154(5) 0.3752(4) 0.03159(9) 0.0389(11) Uani 1 1 d . . . . .
H10A H 0.4839 0.4433 0.0348 0.047 Uiso 1 1 calc R U . . .
H10B H 0.4246 0.3438 0.0097 0.047 Uiso 1 1 calc R U . . .
C20 C 0.0702(4) 0.1863(3) 0.12129(8) 0.0284(9) Uani 1 1 d . . . . .
H20 H 0.0785 0.1008 0.1318 0.034 Uiso 1 1 calc R U . . .
C30 C 0.0662(4) 0.1677(4) 0.19968(8) 0.0326(10) Uani 1 1 d . . . . .
C22 C 0.0885(4) 0.2674(3) 0.17724(9) 0.0323(10) Uani 1 1 d . . . . .
C6 C -0.0271(4) 0.3882(3) 0.06675(8) 0.0327(10) Uani 1 1 d . . . . .
H6A H 0.0471 0.4126 0.0812 0.039 Uiso 1 1 calc R U . . .
H6B H -0.1039 0.4472 0.0705 0.039 Uiso 1 1 calc R U . . .
C8 C 0.1587(4) 0.3460(3) 0.02612(9) 0.0378(11) Uani 1 1 d . . . . .
H8A H 0.1653 0.3276 0.0033 0.045 Uiso 1 1 calc R U . . .
H8B H 0.1673 0.2635 0.0375 0.045 Uiso 1 1 calc R U . . .
C16 C 0.6500(4) 0.2864(4) 0.13991(10) 0.0410(11) Uani 1 1 d . . . . .
H16A H 0.6801 0.3223 0.16 0.062 Uiso 1 1 calc R U . . .
H16B H 0.6664 0.3487 0.1231 0.062 Uiso 1 1 calc R U . . .
H16C H 0.7003 0.2073 0.1355 0.062 Uiso 1 1 calc R U . . .
C11 C 0.4455(4) 0.2644(3) 0.05418(8) 0.0335(10) Uani 1 1 d . . . . .
H11A H 0.3776 0.1956 0.0511 0.04 Uiso 1 1 calc R U . . .
H11B H 0.5358 0.2283 0.0494 0.04 Uiso 1 1 calc R U . . .
C9 C 0.2761(4) 0.4331(4) 0.03557(9) 0.0363(10) Uani 1 1 d . . . . .
H9A H 0.2712 0.5127 0.0229 0.044 Uiso 1 1 calc R U . . .
H9B H 0.2644 0.4577 0.0579 0.044 Uiso 1 1 calc R U . . .
C21 C 0.0167(4) 0.2805(3) 0.14622(8) 0.0331(10) Uani 1 1 d . . . . .
H21A H 0.0278 0.3694 0.1384 0.04 Uiso 1 1 calc R U . . .
H21B H -0.0812 0.2651 0.1494 0.04 Uiso 1 1 calc R U . . .
C25 C 0.1529(5) 0.1924(4) 0.22531(9) 0.0409(11) Uani 1 1 d . . . . .
C23 C 0.1860(5) 0.3457(4) 0.18944(10) 0.0421(11) Uani 1 1 d . . . . .
H23 H 0.222 0.4198 0.1794 0.051 Uiso 1 1 calc R U . . .
C27 C 0.0635(6) 0.0111(5) 0.25260(11) 0.0665(17) Uani 1 1 d . . . . .
H27 H 0.0601 -0.0426 0.2706 0.08 Uiso 1 1 calc R U . . .
C28 C -0.0195(6) -0.0164(4) 0.22725(11) 0.0573(14) Uani 1 1 d . . . . .
H28 H -0.0769 -0.0895 0.228 0.069 Uiso 1 1 calc R U . . .
C26 C 0.1510(6) 0.1142(5) 0.25243(10) 0.0589(15) Uani 1 1 d . . . . .
H26 H 0.2079 0.1319 0.2699 0.071 Uiso 1 1 calc R U . . .
H19 H 0.224(5) 0.311(4) 0.1085(10) 0.071 Uiso 1 1 d . U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O18 C17 1.240(4) . ?
N19 C17 1.357(4) . ?
N19 C20 1.458(5) . ?
N19 H19 0.95(4) . ?
N5 C1 1.345(4) . ?
N5 N4 1.359(4) . ?
N5 C6 1.458(4) . ?
N2 C1 1.325(4) . ?
N2 N3 1.364(4) . ?
N4 N3 1.300(4) . ?
N12 C13 1.453(4) . ?
N12 C11 1.465(4) . ?
N12 H12 0.88 . ?
N24 C25 1.361(5) . ?
N24 C23 1.371(5) . ?
N24 H24 0.88 . ?
C17 C13 1.514(5) . ?
C13 C14 1.554(5) . ?
C13 H13 1 . ?
C29 C28 1.384(5) . ?
C29 C30 1.400(5) . ?
C29 H29 0.95 . ?
C15 C14 1.533(5) . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C7 C8 1.517(5) . ?
C7 C6 1.520(5) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C14 C16 1.523(5) . ?
C14 H14 1 . ?
C1 C20 1.496(5) . ?
C10 C9 1.513(6) . ?
C10 C11 1.532(5) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C20 C21 1.540(5) . ?
C20 H20 1 . ?
C30 C25 1.411(5) . ?
C30 C22 1.428(5) . ?
C22 C23 1.365(5) . ?
C22 C21 1.505(5) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C8 C9 1.527(5) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?
C25 C26 1.413(6) . ?
C23 H23 0.95 . ?
C27 C26 1.379(7) . ?
C27 C28 1.385(7) . ?
C27 H27 0.95 . ?
C28 H28 0.95 . ?
C26 H26 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 N19 C20 122.0(3) . . ?
C17 N19 H19 118(3) . . ?
C20 N19 H19 118(3) . . ?
C1 N5 N4 108.2(3) . . ?
C1 N5 C6 132.9(3) . . ?
N4 N5 C6 118.8(3) . . ?
C1 N2 N3 106.1(3) . . ?
N3 N4 N5 106.5(3) . . ?
C13 N12 C11 113.4(3) . . ?
C13 N12 H12 123.3 . . ?
C11 N12 H12 123.3 . . ?
C25 N24 C23 109.7(4) . . ?
C25 N24 H24 125.1 . . ?
C23 N24 H24 125.1 . . ?
N4 N3 N2 110.7(3) . . ?
O18 C17 N19 122.8(4) . . ?
O18 C17 C13 122.7(3) . . ?
N19 C17 C13 114.5(3) . . ?
N12 C13 C17 110.4(3) . . ?
N12 C13 C14 109.4(3) . . ?
C17 C13 C14 110.1(3) . . ?
N12 C13 H13 109 . . ?
C17 C13 H13 109 . . ?
C14 C13 H13 109 . . ?
C28 C29 C30 119.4(4) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 H29 120.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C7 C6 114.9(3) . . ?
C8 C7 H7A 108.5 . . ?
C6 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
C6 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C16 C14 C15 109.0(3) . . ?
C16 C14 C13 109.9(3) . . ?
C15 C14 C13 112.9(3) . . ?
C16 C14 H14 108.3 . . ?
C15 C14 H14 108.3 . . ?
C13 C14 H14 108.3 . . ?
N2 C1 N5 108.5(3) . . ?
N2 C1 C20 122.3(3) . . ?
N5 C1 C20 128.7(3) . . ?
C9 C10 C11 114.0(3) . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
N19 C20 C1 114.7(3) . . ?
N19 C20 C21 110.6(3) . . ?
C1 C20 C21 110.8(3) . . ?
N19 C20 H20 106.7 . . ?
C1 C20 H20 106.7 . . ?
C21 C20 H20 106.7 . . ?
C29 C30 C25 119.1(4) . . ?
C29 C30 C22 134.0(4) . . ?
C25 C30 C22 106.9(4) . . ?
C23 C22 C30 106.8(4) . . ?
C23 C22 C21 127.8(3) . . ?
C30 C22 C21 125.4(4) . . ?
N5 C6 C7 111.8(3) . . ?
N5 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
N5 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C7 C8 C9 113.6(3) . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N12 C11 C10 111.1(3) . . ?
N12 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
N12 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108 . . ?
C10 C9 C8 115.2(3) . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C8 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C22 C21 C20 112.6(3) . . ?
C22 C21 H21A 109.1 . . ?
C20 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
C20 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
N24 C25 C30 107.3(4) . . ?
N24 C25 C26 131.4(4) . . ?
C30 C25 C26 121.3(5) . . ?
C22 C23 N24 109.3(4) . . ?
C22 C23 H23 125.4 . . ?
N24 C23 H23 125.4 . . ?
C26 C27 C28 121.9(4) . . ?
C26 C27 H27 119 . . ?
C28 C27 H27 119 . . ?
C29 C28 C27 120.8(5) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C27 C26 C25 117.5(5) . . ?
C27 C26 H26 121.3 . . ?
C25 C26 H26 121.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N5 N4 N3 0.2(4) . . . . ?
C6 N5 N4 N3 -177.1(3) . . . . ?
N5 N4 N3 N2 0.0(4) . . . . ?
C1 N2 N3 N4 -0.2(4) . . . . ?
C20 N19 C17 O18 12.2(5) . . . . ?
C20 N19 C17 C13 -165.8(3) . . . . ?
C11 N12 C13 C17 -80.0(4) . . . . ?
C11 N12 C13 C14 158.7(3) . . . . ?
O18 C17 C13 N12 146.9(3) . . . . ?
N19 C17 C13 N12 -35.1(4) . . . . ?
O18 C17 C13 C14 -92.2(4) . . . . ?
N19 C17 C13 C14 85.8(4) . . . . ?
N12 C13 C14 C16 -73.6(4) . . . . ?
C17 C13 C14 C16 164.8(3) . . . . ?
N12 C13 C14 C15 164.4(3) . . . . ?
C17 C13 C14 C15 42.9(4) . . . . ?
N3 N2 C1 N5 0.3(4) . . . . ?
N3 N2 C1 C20 173.4(3) . . . . ?
N4 N5 C1 N2 -0.3(4) . . . . ?
C6 N5 C1 N2 176.4(4) . . . . ?
N4 N5 C1 C20 -172.8(4) . . . . ?
C6 N5 C1 C20 3.9(7) . . . . ?
C17 N19 C20 C1 -110.4(4) . . . . ?
C17 N19 C20 C21 123.4(3) . . . . ?
N2 C1 C20 N19 129.8(4) . . . . ?
N5 C1 C20 N19 -58.7(5) . . . . ?
N2 C1 C20 C21 -104.0(4) . . . . ?
N5 C1 C20 C21 67.5(5) . . . . ?
C28 C29 C30 C25 0.9(6) . . . . ?
C28 C29 C30 C22 -177.8(4) . . . . ?
C29 C30 C22 C23 179.6(4) . . . . ?
C25 C30 C22 C23 0.7(5) . . . . ?
C29 C30 C22 C21 -0.5(7) . . . . ?
C25 C30 C22 C21 -179.4(4) . . . . ?
C1 N5 C6 C7 122.9(4) . . . . ?
N4 N5 C6 C7 -60.7(5) . . . . ?
C8 C7 C6 N5 -74.3(4) . . . . ?
C6 C7 C8 C9 -81.6(4) . . . . ?
C13 N12 C11 C10 171.1(3) . . . . ?
C9 C10 C11 N12 -62.3(4) . . . . ?
C11 C10 C9 C8 -68.1(4) . . . . ?
C7 C8 C9 C10 175.2(3) . . . . ?
C23 C22 C21 C20 103.1(5) . . . . ?
C30 C22 C21 C20 -76.8(5) . . . . ?
N19 C20 C21 C22 -70.5(4) . . . . ?
C1 C20 C21 C22 161.2(3) . . . . ?
C23 N24 C25 C30 0.0(5) . . . . ?
C23 N24 C25 C26 -177.0(5) . . . . ?
C29 C30 C25 N24 -179.5(3) . . . . ?
C22 C30 C25 N24 -0.4(4) . . . . ?
C29 C30 C25 C26 -2.1(6) . . . . ?
C22 C30 C25 C26 177.0(4) . . . . ?
C30 C22 C23 N24 -0.7(5) . . . . ?
C21 C22 C23 N24 179.4(4) . . . . ?
C25 N24 C23 C22 0.5(5) . . . . ?
C30 C29 C28 C27 0.8(7) . . . . ?
C26 C27 C28 C29 -1.5(8) . . . . ?
C28 C27 C26 C25 0.3(7) . . . . ?
N24 C25 C26 C27 178.2(5) . . . . ?
C30 C25 C26 C27 1.5(7) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ig10_f17
_database_code_depnum_ccdc_archive 'CCDC 1844785'
loop_
_audit_author_name
_audit_author_address
'Justyna Kalinowska-Tluscik'
;Jagiellonian University
Poland
;
_audit_update_record             
;
2018-05-22 deposited with the CCDC.	2020-01-07 downloaded from the CCDC.
;

_audit_creation_date             2017-10-20T13:03:34-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C34 H36 N6 O'
_chemical_formula_moiety         'C34 H36 N6 O'
_chemical_formula_weight         544.69

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.2953(14)
_cell_length_b                   11.4120(10)
_cell_length_c                   13.0664(13)
_cell_angle_alpha                70.404(9)
_cell_angle_beta                 73.213(10)
_cell_angle_gamma                70.603(10)
_cell_volume                     1466.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2668
_cell_measurement_theta_min      3.1014
_cell_measurement_theta_max      30.2923

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_F_000             580

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.81708
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.992

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_ub_11      0.0278591
_diffrn_orient_matrix_ub_12      -0.0487118
_diffrn_orient_matrix_ub_13      -0.028615
_diffrn_orient_matrix_ub_21      -0.0076855
_diffrn_orient_matrix_ub_22      -0.0477981
_diffrn_orient_matrix_ub_23      0.0509789
_diffrn_orient_matrix_ub_31      -0.0614904
_diffrn_orient_matrix_ub_32      0.0035999
_diffrn_orient_matrix_ub_33      -0.0063618
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_unetI/netI     0.1226
_diffrn_reflns_number            12639
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.108
_diffrn_reflns_theta_max         30.36
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.896
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.896
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.896
_reflns_Friedel_coverage         0
_reflns_number_total             7920
_reflns_number_gt                4412
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7920
_refine_ls_number_parameters     380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.0717
_refine_ls_wR_factor_ref         0.1931
_refine_ls_wR_factor_gt          0.1428
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.074

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O7 O 0.50792(15) 0.11501(15) 0.57808(14) 0.0261(4) Uani 1 1 d . . . . .
N2 N 0.91306(18) -0.12322(18) 0.57327(16) 0.0237(4) Uani 1 1 d . . . . .
C22 C 0.6909(2) 0.1145(2) 0.20252(18) 0.0179(5) Uani 1 1 d . . . . .
N21 N 0.70361(18) 0.02002(17) 0.31255(15) 0.0182(4) Uani 1 1 d . . . . .
N1 N 0.82311(17) -0.09549(17) 0.51260(15) 0.0194(4) Uani 1 1 d . . . . .
N8 N 0.70102(19) 0.15530(18) 0.53424(16) 0.0212(4) Uani 1 1 d . . . . .
N3 N 1.02257(19) -0.14471(19) 0.50634(17) 0.0252(5) Uani 1 1 d . . . . .
C29 C 0.7772(2) 0.2056(2) 0.17207(18) 0.0179(5) Uani 1 1 d . . . . .
N4 N 1.00779(18) -0.13175(19) 0.40244(16) 0.0239(4) Uani 1 1 d . . . . .
C35 C 0.5522(2) 0.2014(2) 0.21927(19) 0.0213(5) Uani 1 1 d . . . . .
C5 C 0.8830(2) -0.1010(2) 0.40755(18) 0.0188(5) Uani 1 1 d . . . . .
C30 C 0.8571(2) 0.1967(2) 0.23936(19) 0.0226(5) Uani 1 1 d . . . . .
H30 H 0.863 0.1288 0.3056 0.027 Uiso 1 1 calc R U . . .
C33 C 0.8401(2) 0.3962(2) 0.04875(19) 0.0243(5) Uani 1 1 d . . . . .
H33 H 0.834 0.4649 -0.017 0.029 Uiso 1 1 calc R U . . .
C34 C 0.7687(2) 0.3085(2) 0.07626(19) 0.0231(5) Uani 1 1 d . . . . .
H34 H 0.7133 0.3181 0.0298 0.028 Uiso 1 1 calc R U . . .
C18 C 0.9169(2) -0.3318(2) 0.3265(2) 0.0265(5) Uani 1 1 d . . . . .
H18 H 0.9705 -0.3329 0.376 0.032 Uiso 1 1 calc R U . . .
C23 C 0.7173(2) 0.0430(2) 0.11278(18) 0.0210(5) Uani 1 1 d . . . . .
C17 C 0.7955(2) -0.2208(2) 0.33452(19) 0.0231(5) Uani 1 1 d . . . . .
H17A H 0.7405 -0.2432 0.4086 0.028 Uiso 1 1 calc R U . . .
H17B H 0.7476 -0.212 0.2786 0.028 Uiso 1 1 calc R U . . .
C16 C 0.8201(2) -0.0889(2) 0.31667(18) 0.0195(5) Uani 1 1 d . . . . .
H16 H 0.8817 -0.0706 0.2446 0.023 Uiso 1 1 calc R U . . .
C32 C 0.9203(2) 0.3854(2) 0.1157(2) 0.0264(5) Uani 1 1 d . . . . .
H32 H 0.9693 0.446 0.096 0.032 Uiso 1 1 calc R U . . .
C28 C 0.6380(2) -0.0332(2) 0.1233(2) 0.0277(6) Uani 1 1 d . . . . .
H28 H 0.5678 -0.0389 0.1842 0.033 Uiso 1 1 calc R U . . .
C40 C 0.5144(2) 0.2613(2) 0.30500(19) 0.0228(5) Uani 1 1 d . . . . .
H40 H 0.5718 0.244 0.3521 0.027 Uiso 1 1 calc R U . . .
C7 C 0.6258(2) 0.0781(2) 0.55779(18) 0.0197(5) Uani 1 1 d . . . . .
C15 C 0.6674(3) 0.2747(3) 0.7221(2) 0.0345(6) Uani 1 1 d . . . . .
H15 H 0.7519 0.2214 0.7084 0.041 Uiso 1 1 calc R U . . .
C11 C 0.4701(2) 0.3954(2) 0.6640(2) 0.0278(6) Uani 1 1 d . . . . .
H11 H 0.4179 0.4246 0.6103 0.033 Uiso 1 1 calc R U . . .
C36 C 0.4680(2) 0.2305(2) 0.1500(2) 0.0294(6) Uani 1 1 d . . . . .
H36 H 0.4929 0.1927 0.0898 0.035 Uiso 1 1 calc R U . . .
C10 C 0.5947(2) 0.3202(2) 0.64152(19) 0.0217(5) Uani 1 1 d . . . . .
C9 C 0.6485(2) 0.2922(2) 0.52884(19) 0.0234(5) Uani 1 1 d . . . . .
H9A H 0.5796 0.3282 0.4856 0.028 Uiso 1 1 calc R U . . .
H9B H 0.7168 0.337 0.4886 0.028 Uiso 1 1 calc R U . . .
C39 C 0.3941(2) 0.3458(2) 0.3223(2) 0.0298(6) Uani 1 1 d . . . . .
H39 H 0.3698 0.3856 0.3812 0.036 Uiso 1 1 calc R U . . .
C24 C 0.8219(2) 0.0456(2) 0.02469(19) 0.0247(5) Uani 1 1 d . . . . .
H24 H 0.8788 0.0947 0.0171 0.03 Uiso 1 1 calc R U . . .
C14 C 0.6187(3) 0.3057(3) 0.8228(2) 0.0408(7) Uani 1 1 d . . . . .
H14 H 0.6697 0.2737 0.8776 0.049 Uiso 1 1 calc R U . . .
C13 C 0.4957(3) 0.3832(2) 0.8433(2) 0.0347(6) Uani 1 1 d . . . . .
H13 H 0.4626 0.4054 0.9119 0.042 Uiso 1 1 calc R U . . .
C31 C 0.9287(2) 0.2856(2) 0.2115(2) 0.0255(5) Uani 1 1 d . . . . .
H31 H 0.9832 0.2776 0.2582 0.031 Uiso 1 1 calc R U . . .
C25 C 0.8443(3) -0.0228(3) -0.0527(2) 0.0347(6) Uani 1 1 d . . . . .
H25 H 0.9159 -0.0197 -0.1126 0.042 Uiso 1 1 calc R U . . .
C38 C 0.3095(3) 0.3724(2) 0.2543(2) 0.0363(7) Uani 1 1 d . . . . .
H38 H 0.2267 0.4294 0.2666 0.044 Uiso 1 1 calc R U . . .
C6 C 0.6876(2) -0.0635(2) 0.56366(18) 0.0207(5) Uani 1 1 d . . . . .
H6A H 0.6772 -0.1131 0.6426 0.025 Uiso 1 1 calc R U . . .
H6B H 0.6405 -0.0923 0.5274 0.025 Uiso 1 1 calc R U . . .
C27 C 0.6599(3) -0.1007(3) 0.0461(2) 0.0342(6) Uani 1 1 d . . . . .
H27 H 0.6041 -0.1511 0.054 0.041 Uiso 1 1 calc R U . . .
C12 C 0.4209(3) 0.4286(2) 0.7641(2) 0.0325(6) Uani 1 1 d . . . . .
H12 H 0.3364 0.482 0.7779 0.039 Uiso 1 1 calc R U . . .
C26 C 0.7627(3) -0.0950(3) -0.0423(2) 0.0379(7) Uani 1 1 d . . . . .
H26 H 0.777 -0.1406 -0.0956 0.045 Uiso 1 1 calc R U . . .
C37 C 0.3470(2) 0.3149(3) 0.1682(2) 0.0366(7) Uani 1 1 d . . . . .
H37 H 0.2896 0.3331 0.1208 0.044 Uiso 1 1 calc R U . . .
C19 C 0.8820(3) -0.4599(2) 0.3663(3) 0.0448(8) Uani 1 1 d . . . . .
H19A H 0.8307 -0.4696 0.4419 0.067 Uiso 1 1 calc R U . . .
H19B H 0.9604 -0.5305 0.3659 0.067 Uiso 1 1 calc R U . . .
H19C H 0.8323 -0.462 0.3169 0.067 Uiso 1 1 calc R U . . .
C20 C 0.9949(3) -0.3124(3) 0.2084(3) 0.0572(10) Uani 1 1 d . . . . .
H20A H 1.0686 -0.3874 0.2039 0.086 Uiso 1 1 calc R U . . .
H20B H 1.0252 -0.2349 0.1878 0.086 Uiso 1 1 calc R U . . .
H20C H 0.9412 -0.3024 0.1575 0.086 Uiso 1 1 calc R U . . .
H8 H 0.791(3) 0.125(2) 0.524(2) 0.039(8) Uiso 1 1 d . . . . .
H21 H 0.634(2) -0.011(2) 0.338(2) 0.027(7) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O7 C7 1.233(3) . ?
N2 N3 1.293(3) . ?
N2 N1 1.358(2) . ?
C22 N21 1.492(3) . ?
C22 C29 1.537(3) . ?
C22 C35 1.549(3) . ?
C22 C23 1.551(3) . ?
N21 C16 1.480(3) . ?
N21 H21 0.90(3) . ?
N1 C5 1.356(3) . ?
N1 C6 1.458(3) . ?
N8 C7 1.326(3) . ?
N8 C9 1.460(3) . ?
N8 H8 0.94(3) . ?
N3 N4 1.369(3) . ?
C29 C30 1.391(3) . ?
C29 C34 1.402(3) . ?
N4 C5 1.322(3) . ?
C35 C36 1.386(3) . ?
C35 C40 1.395(3) . ?
C5 C16 1.498(3) . ?
C30 C31 1.393(3) . ?
C30 H30 0.95 . ?
C33 C34 1.382(3) . ?
C33 C32 1.382(3) . ?
C33 H33 0.95 . ?
C34 H34 0.95 . ?
C18 C19 1.522(3) . ?
C18 C20 1.524(4) . ?
C18 C17 1.532(3) . ?
C18 H18 1 . ?
C23 C24 1.391(3) . ?
C23 C28 1.395(3) . ?
C17 C16 1.549(3) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C16 H16 1 . ?
C32 C31 1.384(3) . ?
C32 H32 0.95 . ?
C28 C27 1.386(3) . ?
C28 H28 0.95 . ?
C40 C39 1.388(3) . ?
C40 H40 0.95 . ?
C7 C6 1.517(3) . ?
C15 C10 1.378(3) . ?
C15 C14 1.387(3) . ?
C15 H15 0.95 . ?
C11 C10 1.390(3) . ?
C11 C12 1.392(3) . ?
C11 H11 0.95 . ?
C36 C37 1.394(3) . ?
C36 H36 0.95 . ?
C10 C9 1.519(3) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C39 C38 1.383(4) . ?
C39 H39 0.95 . ?
C24 C25 1.396(3) . ?
C24 H24 0.95 . ?
C14 C13 1.383(4) . ?
C14 H14 0.95 . ?
C13 C12 1.381(4) . ?
C13 H13 0.95 . ?
C31 H31 0.95 . ?
C25 C26 1.380(4) . ?
C25 H25 0.95 . ?
C38 C37 1.383(4) . ?
C38 H38 0.95 . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C27 C26 1.382(4) . ?
C27 H27 0.95 . ?
C12 H12 0.95 . ?
C26 H26 0.95 . ?
C37 H37 0.95 . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 N2 N1 105.95(18) . . ?
N21 C22 C29 110.91(17) . . ?
N21 C22 C35 105.40(17) . . ?
C29 C22 C35 105.04(17) . . ?
N21 C22 C23 110.30(17) . . ?
C29 C22 C23 112.58(18) . . ?
C35 C22 C23 112.30(18) . . ?
C16 N21 C22 117.11(17) . . ?
C16 N21 H21 109.0(16) . . ?
C22 N21 H21 107.6(15) . . ?
C5 N1 N2 108.77(18) . . ?
C5 N1 C6 131.32(19) . . ?
N2 N1 C6 119.90(18) . . ?
C7 N8 C9 121.6(2) . . ?
C7 N8 H8 122.9(16) . . ?
C9 N8 H8 115.4(16) . . ?
N2 N3 N4 111.35(17) . . ?
C30 C29 C34 117.9(2) . . ?
C30 C29 C22 123.1(2) . . ?
C34 C29 C22 118.81(19) . . ?
C5 N4 N3 106.07(18) . . ?
C36 C35 C40 118.5(2) . . ?
C36 C35 C22 124.2(2) . . ?
C40 C35 C22 117.1(2) . . ?
N4 C5 N1 107.87(19) . . ?
N4 C5 C16 125.7(2) . . ?
N1 C5 C16 126.1(2) . . ?
C29 C30 C31 121.2(2) . . ?
C29 C30 H30 119.4 . . ?
C31 C30 H30 119.4 . . ?
C34 C33 C32 120.8(2) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C33 C34 C29 120.7(2) . . ?
C33 C34 H34 119.7 . . ?
C29 C34 H34 119.7 . . ?
C19 C18 C20 110.9(2) . . ?
C19 C18 C17 110.2(2) . . ?
C20 C18 C17 110.8(2) . . ?
C19 C18 H18 108.3 . . ?
C20 C18 H18 108.3 . . ?
C17 C18 H18 108.3 . . ?
C24 C23 C28 118.0(2) . . ?
C24 C23 C22 122.7(2) . . ?
C28 C23 C22 119.3(2) . . ?
C18 C17 C16 114.56(19) . . ?
C18 C17 H17A 108.6 . . ?
C16 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
N21 C16 C5 110.62(17) . . ?
N21 C16 C17 114.05(18) . . ?
C5 C16 C17 107.88(18) . . ?
N21 C16 H16 108 . . ?
C5 C16 H16 108 . . ?
C17 C16 H16 108 . . ?
C33 C32 C31 119.4(2) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
C27 C28 C23 121.0(2) . . ?
C27 C28 H28 119.5 . . ?
C23 C28 H28 119.5 . . ?
C39 C40 C35 120.9(2) . . ?
C39 C40 H40 119.6 . . ?
C35 C40 H40 119.6 . . ?
O7 C7 N8 123.2(2) . . ?
O7 C7 C6 118.3(2) . . ?
N8 C7 C6 118.5(2) . . ?
C10 C15 C14 120.9(2) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C10 C11 C12 120.8(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C35 C36 C37 120.3(2) . . ?
C35 C36 H36 119.8 . . ?
C37 C36 H36 119.8 . . ?
C15 C10 C11 118.8(2) . . ?
C15 C10 C9 121.6(2) . . ?
C11 C10 C9 119.6(2) . . ?
N8 C9 C10 113.96(19) . . ?
N8 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
N8 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C38 C39 C40 120.3(2) . . ?
C38 C39 H39 119.8 . . ?
C40 C39 H39 119.8 . . ?
C23 C24 C25 121.0(2) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 120 . . ?
C15 C14 H14 120 . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 120 . . ?
C14 C13 H13 120 . . ?
C32 C31 C30 119.9(2) . . ?
C32 C31 H31 120 . . ?
C30 C31 H31 120 . . ?
C26 C25 C24 120.1(3) . . ?
C26 C25 H25 120 . . ?
C24 C25 H25 120 . . ?
C39 C38 C37 119.1(2) . . ?
C39 C38 H38 120.4 . . ?
C37 C38 H38 120.4 . . ?
N1 C6 C7 115.49(19) . . ?
N1 C6 H6A 108.4 . . ?
C7 C6 H6A 108.4 . . ?
N1 C6 H6B 108.4 . . ?
C7 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
C26 C27 C28 120.3(2) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C25 C26 C27 119.6(2) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C38 C37 C36 120.8(2) . . ?
C38 C37 H37 119.6 . . ?
C36 C37 H37 119.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C29 C22 N21 C16 -76.5(2) . . . . ?
C35 C22 N21 C16 170.31(18) . . . . ?
C23 C22 N21 C16 48.9(2) . . . . ?
N3 N2 N1 C5 -0.1(2) . . . . ?
N3 N2 N1 C6 -178.71(18) . . . . ?
N1 N2 N3 N4 0.1(2) . . . . ?
N21 C22 C29 C30 1.0(3) . . . . ?
C35 C22 C29 C30 114.4(2) . . . . ?
C23 C22 C29 C30 -123.1(2) . . . . ?
N21 C22 C29 C34 -174.03(19) . . . . ?
C35 C22 C29 C34 -60.6(2) . . . . ?
C23 C22 C29 C34 61.8(3) . . . . ?
N2 N3 N4 C5 0.0(2) . . . . ?
N21 C22 C35 C36 -130.7(2) . . . . ?
C29 C22 C35 C36 112.1(2) . . . . ?
C23 C22 C35 C36 -10.6(3) . . . . ?
N21 C22 C35 C40 54.3(2) . . . . ?
C29 C22 C35 C40 -62.9(2) . . . . ?
C23 C22 C35 C40 174.4(2) . . . . ?
N3 N4 C5 N1 -0.1(2) . . . . ?
N3 N4 C5 C16 -173.9(2) . . . . ?
N2 N1 C5 N4 0.1(2) . . . . ?
C6 N1 C5 N4 178.5(2) . . . . ?
N2 N1 C5 C16 173.93(19) . . . . ?
C6 N1 C5 C16 -7.7(4) . . . . ?
C34 C29 C30 C31 -1.4(3) . . . . ?
C22 C29 C30 C31 -176.5(2) . . . . ?
C32 C33 C34 C29 -0.8(3) . . . . ?
C30 C29 C34 C33 1.5(3) . . . . ?
C22 C29 C34 C33 176.87(19) . . . . ?
N21 C22 C23 C24 -114.4(2) . . . . ?
C29 C22 C23 C24 10.1(3) . . . . ?
C35 C22 C23 C24 128.4(2) . . . . ?
N21 C22 C23 C28 61.9(3) . . . . ?
C29 C22 C23 C28 -173.7(2) . . . . ?
C35 C22 C23 C28 -55.3(3) . . . . ?
C19 C18 C17 C16 169.4(2) . . . . ?
C20 C18 C17 C16 -67.5(3) . . . . ?
C22 N21 C16 C5 129.6(2) . . . . ?
C22 N21 C16 C17 -108.6(2) . . . . ?
N4 C5 C16 N21 -141.8(2) . . . . ?
N1 C5 C16 N21 45.4(3) . . . . ?
N4 C5 C16 C17 92.8(3) . . . . ?
N1 C5 C16 C17 -79.9(3) . . . . ?
C18 C17 C16 N21 173.75(19) . . . . ?
C18 C17 C16 C5 -62.9(2) . . . . ?
C34 C33 C32 C31 -0.2(4) . . . . ?
C24 C23 C28 C27 -2.2(3) . . . . ?
C22 C23 C28 C27 -178.7(2) . . . . ?
C36 C35 C40 C39 1.5(3) . . . . ?
C22 C35 C40 C39 176.8(2) . . . . ?
C9 N8 C7 O7 -1.0(3) . . . . ?
C9 N8 C7 C6 -179.05(19) . . . . ?
C40 C35 C36 C37 -1.9(4) . . . . ?
C22 C35 C36 C37 -176.8(2) . . . . ?
C14 C15 C10 C11 -1.6(4) . . . . ?
C14 C15 C10 C9 177.2(2) . . . . ?
C12 C11 C10 C15 2.4(4) . . . . ?
C12 C11 C10 C9 -176.3(2) . . . . ?
C7 N8 C9 C10 75.7(3) . . . . ?
C15 C10 C9 N8 54.7(3) . . . . ?
C11 C10 C9 N8 -126.6(2) . . . . ?
C35 C40 C39 C38 -0.2(4) . . . . ?
C28 C23 C24 C25 1.9(3) . . . . ?
C22 C23 C24 C25 178.2(2) . . . . ?
C10 C15 C14 C13 0.0(4) . . . . ?
C15 C14 C13 C12 0.7(4) . . . . ?
C33 C32 C31 C30 0.4(4) . . . . ?
C29 C30 C31 C32 0.4(4) . . . . ?
C23 C24 C25 C26 -0.3(4) . . . . ?
C40 C39 C38 C37 -0.8(4) . . . . ?
C5 N1 C6 C7 -89.4(3) . . . . ?
N2 N1 C6 C7 88.8(2) . . . . ?
O7 C7 C6 N1 165.1(2) . . . . ?
N8 C7 C6 N1 -16.8(3) . . . . ?
C23 C28 C27 C26 0.9(4) . . . . ?
C14 C13 C12 C11 0.1(4) . . . . ?
C10 C11 C12 C13 -1.7(4) . . . . ?
C24 C25 C26 C27 -1.0(4) . . . . ?
C28 C27 C26 C25 0.7(4) . . . . ?
C39 C38 C37 C36 0.4(4) . . . . ?
C35 C36 C37 C38 0.9(4) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ig15_f31_1
_database_code_depnum_ccdc_archive 'CCDC 1842390'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Kurpiewska' 'Jagiellonian University'
_audit_update_record             
;
2018-05-09 deposited with the CCDC.	2020-01-07 downloaded from the CCDC.
;

_audit_creation_date             2017-10-24T17:46:38-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C33 H33 Cl N6 O'
_chemical_formula_moiety         'C33 H33 Cl N6 O'
_chemical_formula_weight         565.1

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_space_group_name_H-M   'P -1'
_symmetry_cell_setting           triclinic
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1544(3)
_cell_length_b                   10.8644(4)
_cell_length_c                   15.5035(5)
_cell_angle_alpha                72.725(3)
_cell_angle_beta                 84.894(3)
_cell_angle_gamma                83.984(3)
_cell_volume                     1461.55(9)
_cell_measurement_temperature    130.00(10)
_cell_measurement_reflns_used    8564
_cell_measurement_theta_min      2.8446
_cell_measurement_theta_max      28.5060
_cell_oxdiff_length_a            9.1544(3)
_cell_oxdiff_length_b            10.8644(4)
_cell_oxdiff_length_c            15.5035(5)
_cell_oxdiff_angle_alpha         72.725(3)
_cell_oxdiff_angle_beta          84.894(3)
_cell_oxdiff_angle_gamma         83.984(3)
_cell_oxdiff_volume              1461.55(9)
_cell_oxdiff_measurement_reflns_used 8564
_cell_formula_units_Z            2

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             596
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_min  0.87349
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      130.00(10)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_reflns_number            20432
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.8446
_diffrn_reflns_theta_max         28.5060
_diffrn_measured_fraction_theta_max 0.9833
_diffrn_reflns_theta_full        26.3154
_diffrn_measured_fraction_theta_full 0.9983
_reflns_number_total             6744
_reflns_number_gt                5312
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#
_computing_data_collection       
;
         CrysAlisPro, Agilent Technologies,
         Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
         (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
         CrysAlisPro, Agilent Technologies,
         Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
         (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
         CrysAlisPro, Agilent Technologies,
         Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
         (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'


#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      'calc '
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6744
_refine_ls_number_parameters     376
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.0982
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.044

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl41 Cl 0.82545(5) 0.03475(4) 0.42374(3) 0.03659(12) Uani 1 d . . .
O26 O 0.26960(12) -0.38746(10) 0.70861(7) 0.0249(2) Uani 1 d . . .
N33 N 0.52554(14) -0.26590(13) 0.84062(8) 0.0239(3) Uani 1 d . . .
N20 N 0.01446(13) -0.53515(12) 0.75314(8) 0.0198(3) Uani 1 d . . .
N32 N 0.58292(15) -0.22108(14) 0.90184(9) 0.0309(3) Uani 1 d . . .
N30 N 0.63377(14) -0.43139(14) 0.93541(9) 0.0281(3) Uani 1 d . . .
N31 N 0.64735(15) -0.32158(15) 0.95798(9) 0.0316(3) Uani 1 d . . .
N27 N 0.35747(13) -0.51293(12) 0.84063(8) 0.0231(3) Uani 1 d . . .
H27 H 0.3364 -0.5634 0.8937 0.028 Uiso 1 calc R . .
C40 C 0.72484(18) -0.03538(16) 0.52417(11) 0.0284(4) Uani 1 d . . .
C34 C 0.44908(17) -0.17734(16) 0.76364(11) 0.0274(3) Uani 1 d . . .
H34A H 0.4039 -0.1025 0.7808 0.033 Uiso 1 calc R . .
H34B H 0.3712 -0.2207 0.7493 0.033 Uiso 1 calc R . .
C7 C -0.15840(17) -0.57885(16) 0.63058(10) 0.0267(3) Uani 1 d . . .
H7 H -0.2011 -0.5304 0.668 0.032 Uiso 1 calc R . .
C35 C 0.55121(17) -0.13252(15) 0.68042(11) 0.0249(3) Uani 1 d . . .
C12 C -0.03114(16) -0.65984(14) 0.65511(10) 0.0219(3) Uani 1 d . . .
C29 C 0.55747(16) -0.39465(15) 0.86245(10) 0.0234(3) Uani 1 d . . .
C5 C -0.05997(18) -0.88884(16) 0.82394(11) 0.0288(4) Uani 1 d . . .
H5 H 0.0026 -0.9214 0.7838 0.035 Uiso 1 calc R . .
C6 C -0.06206(16) -0.75823(15) 0.81960(10) 0.0211(3) Uani 1 d . . .
C8 C -0.22196(18) -0.56989(17) 0.55077(11) 0.0307(4) Uani 1 d . . .
H8 H -0.3064 -0.5148 0.535 0.037 Uiso 1 calc R . .
C10 C -0.0362(2) -0.72299(17) 0.51863(11) 0.0329(4) Uani 1 d . . .
H10 H 0.0056 -0.7718 0.4812 0.039 Uiso 1 calc R . .
C2 C -0.24829(18) -0.79419(18) 0.94271(11) 0.0313(4) Uani 1 d . . .
H2 H -0.3119 -0.7619 0.9826 0.038 Uiso 1 calc R . .
C22 C 0.00380(17) -0.39078(15) 0.84919(10) 0.0244(3) Uani 1 d . . .
H22 H -0.0876 -0.425 0.8806 0.029 Uiso 1 calc R . .
C19 C 0.03425(16) -0.66898(14) 0.74534(10) 0.0198(3) Uani 1 d . . .
C4 C -0.15003(19) -0.97032(17) 0.88728(12) 0.0341(4) Uani 1 d . . .
H4 H -0.147 -1.0571 0.8898 0.041 Uiso 1 calc R . .
C13 C 0.29608(17) -0.66915(15) 0.67624(10) 0.0245(3) Uani 1 d . . .
H13 H 0.26 -0.6135 0.6231 0.029 Uiso 1 calc R . .
C11 C 0.02825(18) -0.73261(16) 0.59840(11) 0.0276(3) Uani 1 d . . .
H11 H 0.1122 -0.7884 0.6141 0.033 Uiso 1 calc R . .
C18 C 0.19790(16) -0.71938(14) 0.74949(10) 0.0207(3) Uani 1 d . . .
C21 C 0.09390(16) -0.50299(14) 0.82045(10) 0.0200(3) Uani 1 d . . .
H21 H 0.1025 -0.5789 0.8737 0.024 Uiso 1 calc R . .
C3 C -0.24449(19) -0.92275(18) 0.94679(11) 0.0352(4) Uani 1 d . . .
H3 H -0.3051 -0.9773 0.9893 0.042 Uiso 1 calc R . .
C9 C -0.1614(2) -0.64185(17) 0.49434(11) 0.0330(4) Uani 1 d . . .
H9 H -0.2044 -0.6356 0.4409 0.04 Uiso 1 calc R . .
C1 C -0.15775(16) -0.71217(16) 0.87947(10) 0.0243(3) Uani 1 d . . .
H1 H -0.1615 -0.6254 0.8773 0.029 Uiso 1 calc R . .
C25 C 0.24857(16) -0.46376(14) 0.78404(10) 0.0203(3) Uani 1 d . . .
C36 C 0.65188(18) -0.04346(15) 0.67710(11) 0.0287(4) Uani 1 d . . .
H36 H 0.6605 -0.0163 0.7278 0.034 Uiso 1 calc R . .
C38 C 0.54201(18) -0.17466(16) 0.60490(11) 0.0298(4) Uani 1 d . . .
H38 H 0.4771 -0.236 0.6071 0.036 Uiso 1 calc R . .
C14 C 0.44627(18) -0.70057(16) 0.68130(11) 0.0293(4) Uani 1 d . . .
H14 H 0.5095 -0.6672 0.6313 0.035 Uiso 1 calc R . .
C37 C 0.73946(19) 0.00530(16) 0.59901(11) 0.0308(4) Uani 1 d . . .
H37 H 0.807 0.0645 0.5971 0.037 Uiso 1 calc R . .
C28 C 0.50918(16) -0.48357(15) 0.81507(11) 0.0251(3) Uani 1 d . . .
H28A H 0.5197 -0.4438 0.7502 0.03 Uiso 1 calc R . .
H28B H 0.5725 -0.5634 0.8296 0.03 Uiso 1 calc R . .
C23 C 0.08208(19) -0.34764(17) 0.91663(11) 0.0313(4) Uani 1 d . . .
H23A H 0.164 -0.3006 0.886 0.047 Uiso 1 calc R . .
H23B H 0.1169 -0.4222 0.9634 0.047 Uiso 1 calc R . .
H23C H 0.0147 -0.293 0.943 0.047 Uiso 1 calc R . .
C17 C 0.25647(17) -0.80192(16) 0.82792(11) 0.0276(3) Uani 1 d . . .
H17 H 0.1936 -0.8376 0.8776 0.033 Uiso 1 calc R . .
C15 C 0.50281(18) -0.78122(16) 0.76011(12) 0.0308(4) Uani 1 d . . .
H15 H 0.6038 -0.801 0.7638 0.037 Uiso 1 calc R . .
C39 C 0.62869(19) -0.12614(17) 0.52629(12) 0.0319(4) Uani 1 d . . .
H39 H 0.6221 -0.1544 0.4758 0.038 Uiso 1 calc R . .
C16 C 0.40751(18) -0.83201(16) 0.83326(12) 0.0322(4) Uani 1 d . . .
H16 H 0.4445 -0.8867 0.8865 0.039 Uiso 1 calc R . .
C24 C -0.0407(2) -0.27532(17) 0.76955(12) 0.0343(4) Uani 1 d . . .
H24A H -0.1033 -0.213 0.7914 0.051 Uiso 1 calc R . .
H24B H -0.0926 -0.3039 0.7288 0.051 Uiso 1 calc R . .
H24C H 0.0458 -0.2364 0.7383 0.051 Uiso 1 calc R . .
H20 H 0.0384(18) -0.4833(16) 0.7014(11) 0.020(4) Uiso 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl41 C40 1.7438(16) . ?
O26 C25 1.2286(17) . ?
N33 C29 1.344(2) . ?
N33 N32 1.3529(18) . ?
N33 C34 1.472(2) . ?
N20 C21 1.4646(18) . ?
N20 C19 1.4854(19) . ?
N20 H20 0.858(17) . ?
N32 N31 1.300(2) . ?
N30 C29 1.319(2) . ?
N30 N31 1.359(2) . ?
N27 C25 1.3471(19) . ?
N27 C28 1.4517(19) . ?
N27 H27 0.86 . ?
C40 C37 1.380(2) . ?
C40 C39 1.381(2) . ?
C34 C35 1.511(2) . ?
C34 H34A 0.97 . ?
C34 H34B 0.97 . ?
C7 C8 1.387(2) . ?
C7 C12 1.393(2) . ?
C7 H7 0.93 . ?
C35 C38 1.390(2) . ?
C35 C36 1.392(2) . ?
C12 C11 1.390(2) . ?
C12 C19 1.542(2) . ?
C29 C28 1.496(2) . ?
C5 C4 1.386(2) . ?
C5 C6 1.399(2) . ?
C5 H5 0.93 . ?
C6 C1 1.385(2) . ?
C6 C19 1.5423(19) . ?
C8 C9 1.383(3) . ?
C8 H8 0.93 . ?
C10 C9 1.378(3) . ?
C10 C11 1.389(2) . ?
C10 H10 0.93 . ?
C2 C3 1.376(3) . ?
C2 C1 1.391(2) . ?
C2 H2 0.93 . ?
C22 C23 1.524(2) . ?
C22 C24 1.525(2) . ?
C22 C21 1.553(2) . ?
C22 H22 0.98 . ?
C19 C18 1.540(2) . ?
C4 C3 1.383(3) . ?
C4 H4 0.93 . ?
C13 C14 1.385(2) . ?
C13 C18 1.396(2) . ?
C13 H13 0.93 . ?
C11 H11 0.93 . ?
C18 C17 1.392(2) . ?
C21 C25 1.532(2) . ?
C21 H21 0.98 . ?
C3 H3 0.93 . ?
C9 H9 0.93 . ?
C1 H1 0.93 . ?
C36 C37 1.387(2) . ?
C36 H36 0.93 . ?
C38 C39 1.388(2) . ?
C38 H38 0.93 . ?
C14 C15 1.382(2) . ?
C14 H14 0.93 . ?
C37 H37 0.93 . ?
C28 H28A 0.97 . ?
C28 H28B 0.97 . ?
C23 H23A 0.96 . ?
C23 H23B 0.96 . ?
C23 H23C 0.96 . ?
C17 C16 1.391(2) . ?
C17 H17 0.93 . ?
C15 C16 1.380(2) . ?
C15 H15 0.93 . ?
C39 H39 0.93 . ?
C16 H16 0.93 . ?
C24 H24A 0.96 . ?
C24 H24B 0.96 . ?
C24 H24C 0.96 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C29 N33 N32 108.37(13) . . ?
C29 N33 C34 130.39(13) . . ?
N32 N33 C34 121.19(13) . . ?
C21 N20 C19 119.18(11) . . ?
C21 N20 H20 107.1(11) . . ?
C19 N20 H20 108.0(11) . . ?
N31 N32 N33 105.94(13) . . ?
C29 N30 N31 105.59(13) . . ?
N32 N31 N30 111.31(13) . . ?
C25 N27 C28 122.17(13) . . ?
C25 N27 H27 118.9 . . ?
C28 N27 H27 118.9 . . ?
C37 C40 C39 121.53(15) . . ?
C37 C40 Cl41 118.79(13) . . ?
C39 C40 Cl41 119.64(13) . . ?
N33 C34 C35 112.54(13) . . ?
N33 C34 H34A 109.1 . . ?
C35 C34 H34A 109.1 . . ?
N33 C34 H34B 109.1 . . ?
C35 C34 H34B 109.1 . . ?
H34A C34 H34B 107.8 . . ?
C8 C7 C12 120.54(16) . . ?
C8 C7 H7 119.7 . . ?
C12 C7 H7 119.7 . . ?
C38 C35 C36 119.01(15) . . ?
C38 C35 C34 120.89(14) . . ?
C36 C35 C34 120.04(14) . . ?
C11 C12 C7 118.23(14) . . ?
C11 C12 C19 122.85(14) . . ?
C7 C12 C19 118.87(14) . . ?
N30 C29 N33 108.79(14) . . ?
N30 C29 C28 125.07(15) . . ?
N33 C29 C28 126.09(14) . . ?
C4 C5 C6 120.80(16) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.28(14) . . ?
C1 C6 C19 122.24(14) . . ?
C5 C6 C19 119.37(13) . . ?
C9 C8 C7 120.83(16) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C9 C10 C11 120.70(17) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C3 C2 C1 120.48(16) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C23 C22 C24 110.65(14) . . ?
C23 C22 C21 112.08(13) . . ?
C24 C22 C21 113.59(13) . . ?
C23 C22 H22 106.7 . . ?
C24 C22 H22 106.7 . . ?
C21 C22 H22 106.7 . . ?
N20 C19 C18 110.41(11) . . ?
N20 C19 C6 110.24(12) . . ?
C18 C19 C6 111.61(12) . . ?
N20 C19 C12 105.02(11) . . ?
C18 C19 C12 113.62(12) . . ?
C6 C19 C12 105.66(11) . . ?
C3 C4 C5 120.12(16) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C14 C13 C18 121.22(15) . . ?
C14 C13 H13 119.4 . . ?
C18 C13 H13 119.4 . . ?
C10 C11 C12 120.80(16) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C17 C18 C13 117.58(14) . . ?
C17 C18 C19 122.47(13) . . ?
C13 C18 C19 119.46(13) . . ?
N20 C21 C25 112.06(12) . . ?
N20 C21 C22 108.72(12) . . ?
C25 C21 C22 109.81(12) . . ?
N20 C21 H21 108.7 . . ?
C25 C21 H21 108.7 . . ?
C22 C21 H21 108.7 . . ?
C2 C3 C4 119.59(15) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C10 C9 C8 118.89(15) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C6 C1 C2 120.71(15) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
O26 C25 N27 122.47(13) . . ?
O26 C25 C21 121.15(13) . . ?
N27 C25 C21 116.32(13) . . ?
C37 C36 C35 120.75(15) . . ?
C37 C36 H36 119.6 . . ?
C35 C36 H36 119.6 . . ?
C39 C38 C35 120.71(15) . . ?
C39 C38 H38 119.6 . . ?
C35 C38 H38 119.6 . . ?
C15 C14 C13 120.47(15) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C40 C37 C36 118.96(15) . . ?
C40 C37 H37 120.5 . . ?
C36 C37 H37 120.5 . . ?
N27 C28 C29 112.12(13) . . ?
N27 C28 H28A 109.2 . . ?
C29 C28 H28A 109.2 . . ?
N27 C28 H28B 109.2 . . ?
C29 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C16 C17 C18 121.10(15) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C16 C15 C14 119.17(15) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C40 C39 C38 118.99(16) . . ?
C40 C39 H39 120.5 . . ?
C38 C39 H39 120.5 . . ?
C15 C16 C17 120.44(16) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C29 N33 N32 N31 0.20(16) . . . . ?
C34 N33 N32 N31 -177.35(13) . . . . ?
N33 N32 N31 N30 -0.07(16) . . . . ?
C29 N30 N31 N32 -0.09(17) . . . . ?
C29 N33 C34 C35 -85.29(19) . . . . ?
N32 N33 C34 C35 91.65(17) . . . . ?
N33 C34 C35 C38 109.76(17) . . . . ?
N33 C34 C35 C36 -73.10(19) . . . . ?
C8 C7 C12 C11 -1.1(2) . . . . ?
C8 C7 C12 C19 -178.81(13) . . . . ?
N31 N30 C29 N33 0.22(16) . . . . ?
N31 N30 C29 C28 -177.17(14) . . . . ?
N32 N33 C29 N30 -0.27(16) . . . . ?
C34 N33 C29 N30 176.98(14) . . . . ?
N32 N33 C29 C28 177.09(14) . . . . ?
C34 N33 C29 C28 -5.7(2) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
C4 C5 C6 C19 -177.13(14) . . . . ?
C12 C7 C8 C9 0.6(2) . . . . ?
C21 N20 C19 C18 -43.35(16) . . . . ?
C21 N20 C19 C6 80.42(15) . . . . ?
C21 N20 C19 C12 -166.20(12) . . . . ?
C1 C6 C19 N20 3.56(19) . . . . ?
C5 C6 C19 N20 179.75(13) . . . . ?
C1 C6 C19 C18 126.64(15) . . . . ?
C5 C6 C19 C18 -57.18(17) . . . . ?
C1 C6 C19 C12 -109.40(15) . . . . ?
C5 C6 C19 C12 66.78(17) . . . . ?
C11 C12 C19 N20 143.95(14) . . . . ?
C7 C12 C19 N20 -38.48(17) . . . . ?
C11 C12 C19 C18 23.20(19) . . . . ?
C7 C12 C19 C18 -159.24(13) . . . . ?
C11 C12 C19 C6 -99.48(16) . . . . ?
C7 C12 C19 C6 78.08(16) . . . . ?
C6 C5 C4 C3 0.5(3) . . . . ?
C9 C10 C11 C12 -0.6(2) . . . . ?
C7 C12 C11 C10 1.1(2) . . . . ?
C19 C12 C11 C10 178.71(14) . . . . ?
C14 C13 C18 C17 0.2(2) . . . . ?
C14 C13 C18 C19 172.41(14) . . . . ?
N20 C19 C18 C17 100.19(16) . . . . ?
C6 C19 C18 C17 -22.80(19) . . . . ?
C12 C19 C18 C17 -142.14(14) . . . . ?
N20 C19 C18 C13 -71.65(17) . . . . ?
C6 C19 C18 C13 165.37(13) . . . . ?
C12 C19 C18 C13 46.03(18) . . . . ?
C19 N20 C21 C25 86.33(15) . . . . ?
C19 N20 C21 C22 -152.12(12) . . . . ?
C23 C22 C21 N20 -177.73(12) . . . . ?
C24 C22 C21 N20 -51.39(17) . . . . ?
C23 C22 C21 C25 -54.80(16) . . . . ?
C24 C22 C21 C25 71.53(16) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C5 C4 C3 C2 -0.1(3) . . . . ?
C11 C10 C9 C8 0.0(2) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
C5 C6 C1 C2 0.6(2) . . . . ?
C19 C6 C1 C2 176.80(14) . . . . ?
C3 C2 C1 C6 -0.1(2) . . . . ?
C28 N27 C25 O26 -2.7(2) . . . . ?
C28 N27 C25 C21 -179.83(13) . . . . ?
N20 C21 C25 O26 45.94(19) . . . . ?
C22 C21 C25 O26 -74.99(17) . . . . ?
N20 C21 C25 N27 -136.87(13) . . . . ?
C22 C21 C25 N27 102.20(15) . . . . ?
C38 C35 C36 C37 1.6(2) . . . . ?
C34 C35 C36 C37 -175.61(15) . . . . ?
C36 C35 C38 C39 -1.8(2) . . . . ?
C34 C35 C38 C39 175.33(15) . . . . ?
C18 C13 C14 C15 -1.1(2) . . . . ?
C39 C40 C37 C36 -2.0(3) . . . . ?
Cl41 C40 C37 C36 175.44(13) . . . . ?
C35 C36 C37 C40 0.3(3) . . . . ?
C25 N27 C28 C29 107.54(16) . . . . ?
N30 C29 C28 N27 98.50(17) . . . . ?
N33 C29 C28 N27 -78.44(19) . . . . ?
C13 C18 C17 C16 0.7(2) . . . . ?
C19 C18 C17 C16 -171.31(15) . . . . ?
C13 C14 C15 C16 1.2(3) . . . . ?
C37 C40 C39 C38 1.8(3) . . . . ?
Cl41 C40 C39 C38 -175.67(13) . . . . ?
C35 C38 C39 C40 0.2(3) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C18 C17 C16 C15 -0.6(3) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ea724f25
_database_code_depnum_ccdc_archive 'CCDC 1844786'
loop_
_audit_author_name
_audit_author_address
'Justyna Kalinowska-Tluscik'
;Jagiellonian University
Poland
;
_audit_update_record             
;
2018-05-22 deposited with the CCDC.	2020-01-07 downloaded from the CCDC.
;

_audit_creation_date             2018-01-29T17:45:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C32 H35 N7 O'
_chemical_formula_moiety         'C32 H35 N7 O'
_chemical_formula_weight         533.67
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.7885(4)
_cell_length_b                   7.9643(4)
_cell_length_c                   26.039(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.113(6)
_cell_angle_gamma                90
_cell_volume                     1404.17(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    4565
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      25.709

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_F_000             568

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.08
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.62062
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.998

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_ambient_temperature      130(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0537901
_diffrn_orient_matrix_ub_12      -0.0038974
_diffrn_orient_matrix_ub_13      0.0223381
_diffrn_orient_matrix_ub_21      -0.0892024
_diffrn_orient_matrix_ub_22      -0.0082806
_diffrn_orient_matrix_ub_23      -0.0157386
_diffrn_orient_matrix_ub_31      0.0105601
_diffrn_orient_matrix_ub_32      -0.0885664
_diffrn_orient_matrix_ub_33      0.0005134
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_av_unetI/netI     0.0822
_diffrn_reflns_number            19388
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.008
_diffrn_reflns_theta_max         28.73
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.939
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.911
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.88
_reflns_Friedel_coverage         0.814
_reflns_number_total             6631
_reflns_number_gt                5204
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0517P)²+1.8210P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6631
_refine_ls_number_parameters     373
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0799
_refine_ls_wR_factor_ref         0.1845
_refine_ls_wR_factor_gt          0.1706
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1895 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.063

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.3654(6) 0.3372(5) 0.24786(18) 0.0286(9) Uani 1 1 d . . . . .
N1 N 0.2452(6) 0.0156(5) 0.29902(16) 0.0256(9) Uani 1 1 d . . . . .
C30 C 0.5056(7) -0.1227(6) 0.2535(2) 0.0268(10) Uani 1 1 d . . . . .
O30 O 0.4869(6) -0.2748(5) 0.25115(16) 0.0413(10) Uani 1 1 d . . . . .
C28 C 0.1868(7) -0.0828(6) 0.4391(2) 0.0253(10) Uani 1 1 d . . . . .
H28 H 0.134 -0.1563 0.4129 0.03 Uiso 1 1 calc R U . . .
N3 N -0.0590(6) -0.0441(6) 0.30092(18) 0.0329(10) Uani 1 1 d . . . . .
N4 N -0.0472(6) 0.1253(5) 0.29470(19) 0.0321(10) Uani 1 1 d . . . . .
N31 N 0.5671(7) -0.0278(6) 0.21535(18) 0.0325(10) Uani 1 1 d . . . . .
C34 C 0.9506(8) -0.1166(7) 0.1205(2) 0.0342(12) Uani 1 1 d . . . . .
C13 C 0.4151(7) 0.3267(7) 0.1544(2) 0.0312(11) Uani 1 1 d . . . . .
C29 C 0.3709(6) -0.0073(6) 0.43483(18) 0.0229(10) Uani 1 1 d . . . . .
C6 C 0.2278(7) 0.3364(6) 0.2893(2) 0.0274(11) Uani 1 1 d . . . . .
N23 N 0.6232(7) 0.1621(6) 0.46174(19) 0.0346(11) Uani 1 1 d . . . . .
C18 C 0.5920(8) 0.4164(7) 0.1610(2) 0.0338(12) Uani 1 1 d . . . . .
H18 H 0.6303 0.4648 0.1935 0.041 Uiso 1 1 calc R U . . .
C22 C 0.6687(7) 0.0901(6) 0.4163(2) 0.0295(11) Uani 1 1 d . . . . .
H22 H 0.7865 0.1105 0.3997 0.035 Uiso 1 1 calc R U . . .
C21 C 0.5195(7) -0.0161(6) 0.39811(19) 0.0271(10) Uani 1 1 d . . . . .
C27 C 0.0810(7) -0.0499(6) 0.4818(2) 0.0308(11) Uani 1 1 d . . . . .
H27 H -0.0446 -0.1003 0.4846 0.037 Uiso 1 1 calc R U . . .
N2 N 0.1169(6) -0.1122(5) 0.30354(18) 0.0316(10) Uani 1 1 d . . . . .
C25 C 0.3381(8) 0.1354(7) 0.5178(2) 0.0330(12) Uani 1 1 d . . . . .
H25 H 0.3898 0.2082 0.5443 0.04 Uiso 1 1 calc R U . . .
C5 C 0.1437(7) 0.1622(6) 0.2937(2) 0.0256(10) Uani 1 1 d . . . . .
C24 C 0.4415(7) 0.1049(6) 0.4748(2) 0.0286(11) Uani 1 1 d . . . . .
C19 C 0.4582(7) -0.0224(6) 0.30142(19) 0.0251(10) Uani 1 1 d . . . . .
H19 H 0.5333 0.0857 0.3019 0.03 Uiso 1 1 calc R U . . .
C10 C 0.0560(8) 0.4642(7) 0.2846(2) 0.0367(13) Uani 1 1 d . . . . .
H10A H 0.0998 0.5715 0.27 0.044 Uiso 1 1 calc R U . . .
H10B H -0.0559 0.4196 0.2622 0.044 Uiso 1 1 calc R U . . .
C7 C 0.3351(8) 0.3880(7) 0.3407(2) 0.0336(12) Uani 1 1 d . . . . .
H7A H 0.4197 0.4875 0.3363 0.04 Uiso 1 1 calc R U . . .
H7B H 0.4182 0.295 0.3553 0.04 Uiso 1 1 calc R U . . .
C20 C 0.5201(7) -0.1214(7) 0.35059(19) 0.0278(10) Uani 1 1 d . . . . .
H20A H 0.4286 -0.2172 0.3536 0.033 Uiso 1 1 calc R U . . .
H20B H 0.6543 -0.1675 0.3478 0.033 Uiso 1 1 calc R U . . .
C14 C 0.3662(9) 0.2566(8) 0.1065(2) 0.0411(14) Uani 1 1 d . . . . .
H14 H 0.2465 0.1951 0.1011 0.049 Uiso 1 1 calc R U . . .
C36 C 1.2156(9) -0.2979(7) 0.0957(3) 0.0404(14) Uani 1 1 d . . . . .
H36 H 1.3325 -0.3597 0.1051 0.048 Uiso 1 1 calc R U . . .
C35 C 1.1242(8) -0.2086(8) 0.1332(2) 0.0383(13) Uani 1 1 d . . . . .
H35 H 1.1795 -0.2096 0.1677 0.046 Uiso 1 1 calc R U . . .
C26 C 0.1599(8) 0.0582(7) 0.5210(2) 0.0344(12) Uani 1 1 d . . . . .
H26 H 0.0873 0.0776 0.5503 0.041 Uiso 1 1 calc R U . . .
C17 C 0.7123(9) 0.4355(7) 0.1204(2) 0.0398(14) Uani 1 1 d . . . . .
H17 H 0.8331 0.4954 0.1257 0.048 Uiso 1 1 calc R U . . .
C12 C 0.2724(7) 0.3173(7) 0.1961(2) 0.0341(12) Uani 1 1 d . . . . .
H12A H 0.1712 0.4059 0.1899 0.041 Uiso 1 1 calc R U . . .
H12B H 0.2041 0.2074 0.1938 0.041 Uiso 1 1 calc R U . . .
C16 C 0.6586(9) 0.3687(8) 0.0728(2) 0.0429(14) Uani 1 1 d . . . . .
H16 H 0.7377 0.3872 0.0447 0.051 Uiso 1 1 calc R U . . .
C9 C -0.0048(9) 0.4898(7) 0.3399(2) 0.0426(14) Uani 1 1 d . . . . .
H9A H -0.0319 0.6099 0.3462 0.051 Uiso 1 1 calc R U . . .
H9B H -0.1251 0.4242 0.3456 0.051 Uiso 1 1 calc R U . . .
C37 C 1.1395(9) -0.2982(8) 0.0455(3) 0.0440(15) Uani 1 1 d . . . . .
H37 H 1.202 -0.3597 0.02 0.053 Uiso 1 1 calc R U . . .
C39 C 0.8793(8) -0.1180(8) 0.0702(2) 0.0433(15) Uani 1 1 d . . . . .
H39 H 0.7633 -0.0556 0.0604 0.052 Uiso 1 1 calc R U . . .
C32 C 0.6487(8) -0.0990(8) 0.1703(2) 0.0416(14) Uani 1 1 d . . . . .
H32A H 0.5581 -0.0761 0.1396 0.05 Uiso 1 1 calc R U . . .
H32B H 0.6598 -0.2223 0.1744 0.05 Uiso 1 1 calc R U . . .
C33 C 0.8501(9) -0.0267(8) 0.1620(3) 0.0451(15) Uani 1 1 d . . . . .
H33A H 0.8356 0.0934 0.1527 0.054 Uiso 1 1 calc R U . . .
H33B H 0.9341 -0.0337 0.1946 0.054 Uiso 1 1 calc R U . . .
C8 C 0.1685(9) 0.4291(7) 0.3757(2) 0.0409(14) Uani 1 1 d . . . . .
H8A H 0.1311 0.3279 0.3948 0.049 Uiso 1 1 calc R U . . .
H8B H 0.2108 0.5177 0.4007 0.049 Uiso 1 1 calc R U . . .
C38 C 0.9696(9) -0.2069(11) 0.0329(2) 0.0529(18) Uani 1 1 d . . . . .
H38 H 0.9146 -0.2054 -0.0017 0.064 Uiso 1 1 calc R U . . .
C15 C 0.4867(9) 0.2737(8) 0.0663(2) 0.0452(15) Uani 1 1 d . . . . .
H15 H 0.4524 0.2205 0.0343 0.054 Uiso 1 1 calc R U . . .
H11 H 0.429(7) 0.422(7) 0.2485(18) 0.014(13) Uiso 1 1 d . . . . .
H31 H 0.571(10) 0.081(10) 0.220(3) 0.06(2) Uiso 1 1 d . . . . .
H23 H 0.693(11) 0.245(11) 0.479(3) 0.07(2) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C12 1.455(7) . ?
N11 C6 1.477(6) . ?
N11 H11 0.80(5) . ?
N1 N2 1.351(5) . ?
N1 C5 1.358(6) . ?
N1 C19 1.474(6) . ?
C30 O30 1.219(6) . ?
C30 N31 1.339(7) . ?
C30 C19 1.534(7) . ?
C28 C27 1.391(7) . ?
C28 C29 1.398(6) . ?
C28 H28 0.95 . ?
N3 N2 1.308(6) . ?
N3 N4 1.362(6) . ?
N4 C5 1.331(6) . ?
N31 C32 1.449(7) . ?
N31 H31 0.87(8) . ?
C34 C39 1.364(8) . ?
C34 C35 1.407(8) . ?
C34 C33 1.501(8) . ?
C13 C14 1.386(8) . ?
C13 C18 1.397(7) . ?
C13 C12 1.507(7) . ?
C29 C24 1.428(7) . ?
C29 C21 1.441(7) . ?
C6 C5 1.508(7) . ?
C6 C7 1.534(7) . ?
C6 C10 1.545(7) . ?
N23 C22 1.370(7) . ?
N23 C24 1.380(7) . ?
N23 H23 0.92(8) . ?
C18 C17 1.389(8) . ?
C18 H18 0.95 . ?
C22 C21 1.377(7) . ?
C22 H22 0.95 . ?
C21 C20 1.495(7) . ?
C27 C26 1.411(8) . ?
C27 H27 0.95 . ?
C25 C26 1.365(8) . ?
C25 C24 1.385(7) . ?
C25 H25 0.95 . ?
C19 C20 1.537(7) . ?
C19 H19 1 . ?
C10 C9 1.539(8) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C7 C8 1.537(8) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?
C14 C15 1.379(8) . ?
C14 H14 0.95 . ?
C36 C37 1.371(9) . ?
C36 C35 1.389(8) . ?
C36 H36 0.95 . ?
C35 H35 0.95 . ?
C26 H26 0.95 . ?
C17 C16 1.374(9) . ?
C17 H17 0.95 . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C16 C15 1.391(9) . ?
C16 H16 0.95 . ?
C9 C8 1.526(9) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C37 C38 1.383(9) . ?
C37 H37 0.95 . ?
C39 C38 1.380(9) . ?
C39 H39 0.95 . ?
C32 C33 1.513(8) . ?
C32 H32A 0.99 . ?
C32 H32B 0.99 . ?
C33 H33A 0.99 . ?
C33 H33B 0.99 . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C38 H38 0.95 . ?
C15 H15 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N11 C6 114.9(4) . . ?
C12 N11 H11 108(4) . . ?
C6 N11 H11 111(4) . . ?
N2 N1 C5 109.4(4) . . ?
N2 N1 C19 118.6(4) . . ?
C5 N1 C19 132.1(4) . . ?
O30 C30 N31 124.0(5) . . ?
O30 C30 C19 122.1(5) . . ?
N31 C30 C19 113.8(4) . . ?
C27 C28 C29 119.9(4) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 H28 120.1 . . ?
N2 N3 N4 110.8(4) . . ?
C5 N4 N3 106.7(4) . . ?
C30 N31 C32 122.6(5) . . ?
C30 N31 H31 118(5) . . ?
C32 N31 H31 119(5) . . ?
C39 C34 C35 117.1(5) . . ?
C39 C34 C33 123.2(5) . . ?
C35 C34 C33 119.7(5) . . ?
C14 C13 C18 117.6(5) . . ?
C14 C13 C12 120.3(5) . . ?
C18 C13 C12 121.9(5) . . ?
C28 C29 C24 117.8(4) . . ?
C28 C29 C21 134.8(4) . . ?
C24 C29 C21 107.4(4) . . ?
N11 C6 C5 108.8(4) . . ?
N11 C6 C7 110.5(4) . . ?
C5 C6 C7 109.8(4) . . ?
N11 C6 C10 116.9(4) . . ?
C5 C6 C10 108.9(4) . . ?
C7 C6 C10 101.6(4) . . ?
C22 N23 C24 109.6(5) . . ?
C22 N23 H23 126(5) . . ?
C24 N23 H23 124(5) . . ?
C17 C18 C13 120.7(5) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
N23 C22 C21 110.4(5) . . ?
N23 C22 H22 124.8 . . ?
C21 C22 H22 124.8 . . ?
C22 C21 C29 106.0(4) . . ?
C22 C21 C20 125.7(4) . . ?
C29 C21 C20 128.3(4) . . ?
C28 C27 C26 120.1(5) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
N3 N2 N1 106.0(4) . . ?
C26 C25 C24 118.3(5) . . ?
C26 C25 H25 120.9 . . ?
C24 C25 H25 120.9 . . ?
N4 C5 N1 107.2(4) . . ?
N4 C5 C6 125.4(4) . . ?
N1 C5 C6 127.4(4) . . ?
N23 C24 C25 130.9(5) . . ?
N23 C24 C29 106.7(5) . . ?
C25 C24 C29 122.4(5) . . ?
N1 C19 C30 109.6(4) . . ?
N1 C19 C20 110.5(4) . . ?
C30 C19 C20 110.4(4) . . ?
N1 C19 H19 108.8 . . ?
C30 C19 H19 108.8 . . ?
C20 C19 H19 108.8 . . ?
C9 C10 C6 105.3(4) . . ?
C9 C10 H10A 110.7 . . ?
C6 C10 H10A 110.7 . . ?
C9 C10 H10B 110.7 . . ?
C6 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
C6 C7 C8 104.5(4) . . ?
C6 C7 H7A 110.9 . . ?
C8 C7 H7A 110.9 . . ?
C6 C7 H7B 110.9 . . ?
C8 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
C21 C20 C19 112.6(4) . . ?
C21 C20 H20A 109.1 . . ?
C19 C20 H20A 109.1 . . ?
C21 C20 H20B 109.1 . . ?
C19 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
C15 C14 C13 121.7(6) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C37 C36 C35 120.9(6) . . ?
C37 C36 H36 119.6 . . ?
C35 C36 H36 119.6 . . ?
C36 C35 C34 120.7(6) . . ?
C36 C35 H35 119.6 . . ?
C34 C35 H35 119.6 . . ?
C25 C26 C27 121.5(5) . . ?
C25 C26 H26 119.3 . . ?
C27 C26 H26 119.3 . . ?
C16 C17 C18 120.7(6) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
N11 C12 C13 113.7(4) . . ?
N11 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
N11 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C17 C16 C15 119.1(5) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C8 C9 C10 106.4(4) . . ?
C8 C9 H9A 110.4 . . ?
C10 C9 H9A 110.4 . . ?
C8 C9 H9B 110.4 . . ?
C10 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
C36 C37 C38 118.5(6) . . ?
C36 C37 H37 120.8 . . ?
C38 C37 H37 120.8 . . ?
C34 C39 C38 122.4(5) . . ?
C34 C39 H39 118.8 . . ?
C38 C39 H39 118.8 . . ?
N31 C32 C33 111.6(5) . . ?
N31 C32 H32A 109.3 . . ?
C33 C32 H32A 109.3 . . ?
N31 C32 H32B 109.3 . . ?
C33 C32 H32B 109.3 . . ?
H32A C32 H32B 108 . . ?
C34 C33 C32 112.5(5) . . ?
C34 C33 H33A 109.1 . . ?
C32 C33 H33A 109.1 . . ?
C34 C33 H33B 109.1 . . ?
C32 C33 H33B 109.1 . . ?
H33A C33 H33B 107.8 . . ?
C9 C8 C7 105.9(5) . . ?
C9 C8 H8A 110.6 . . ?
C7 C8 H8A 110.6 . . ?
C9 C8 H8B 110.6 . . ?
C7 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
C39 C38 C37 120.5(6) . . ?
C39 C38 H38 119.8 . . ?
C37 C38 H38 119.8 . . ?
C14 C15 C16 120.0(6) . . ?
C14 C15 H15 120 . . ?
C16 C15 H15 120 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N3 N4 C5 -0.2(6) . . . . ?
O30 C30 N31 C32 -10.4(8) . . . . ?
C19 C30 N31 C32 170.0(5) . . . . ?
C27 C28 C29 C24 -1.3(7) . . . . ?
C27 C28 C29 C21 177.7(5) . . . . ?
C12 N11 C6 C5 69.1(5) . . . . ?
C12 N11 C6 C7 -170.3(4) . . . . ?
C12 N11 C6 C10 -54.8(6) . . . . ?
C14 C13 C18 C17 0.7(8) . . . . ?
C12 C13 C18 C17 -174.2(5) . . . . ?
C24 N23 C22 C21 0.0(6) . . . . ?
N23 C22 C21 C29 0.5(6) . . . . ?
N23 C22 C21 C20 -177.7(5) . . . . ?
C28 C29 C21 C22 -179.9(5) . . . . ?
C24 C29 C21 C22 -0.8(5) . . . . ?
C28 C29 C21 C20 -1.8(9) . . . . ?
C24 C29 C21 C20 177.3(5) . . . . ?
C29 C28 C27 C26 -0.5(7) . . . . ?
N4 N3 N2 N1 0.1(6) . . . . ?
C5 N1 N2 N3 0.1(5) . . . . ?
C19 N1 N2 N3 179.0(4) . . . . ?
N3 N4 C5 N1 0.3(6) . . . . ?
N3 N4 C5 C6 -177.7(5) . . . . ?
N2 N1 C5 N4 -0.2(6) . . . . ?
C19 N1 C5 N4 -179.0(5) . . . . ?
N2 N1 C5 C6 177.7(5) . . . . ?
C19 N1 C5 C6 -1.0(9) . . . . ?
N11 C6 C5 N4 -130.1(5) . . . . ?
C7 C6 C5 N4 108.8(6) . . . . ?
C10 C6 C5 N4 -1.6(7) . . . . ?
N11 C6 C5 N1 52.3(7) . . . . ?
C7 C6 C5 N1 -68.8(6) . . . . ?
C10 C6 C5 N1 -179.2(5) . . . . ?
C22 N23 C24 C25 176.7(5) . . . . ?
C22 N23 C24 C29 -0.6(6) . . . . ?
C26 C25 C24 N23 -178.7(5) . . . . ?
C26 C25 C24 C29 -1.8(8) . . . . ?
C28 C29 C24 N23 -179.9(4) . . . . ?
C21 C29 C24 N23 0.9(5) . . . . ?
C28 C29 C24 C25 2.5(7) . . . . ?
C21 C29 C24 C25 -176.7(5) . . . . ?
N2 N1 C19 C30 68.2(5) . . . . ?
C5 N1 C19 C30 -113.1(6) . . . . ?
N2 N1 C19 C20 -53.7(6) . . . . ?
C5 N1 C19 C20 125.0(5) . . . . ?
O30 C30 C19 N1 -84.7(6) . . . . ?
N31 C30 C19 N1 95.0(5) . . . . ?
O30 C30 C19 C20 37.2(6) . . . . ?
N31 C30 C19 C20 -143.2(4) . . . . ?
N11 C6 C10 C9 -156.5(4) . . . . ?
C5 C6 C10 C9 79.7(5) . . . . ?
C7 C6 C10 C9 -36.1(5) . . . . ?
N11 C6 C7 C8 164.8(4) . . . . ?
C5 C6 C7 C8 -75.2(5) . . . . ?
C10 C6 C7 C8 40.0(5) . . . . ?
C22 C21 C20 C19 -82.1(6) . . . . ?
C29 C21 C20 C19 100.1(6) . . . . ?
N1 C19 C20 C21 -71.4(5) . . . . ?
C30 C19 C20 C21 167.2(4) . . . . ?
C18 C13 C14 C15 0.1(9) . . . . ?
C12 C13 C14 C15 175.1(6) . . . . ?
C37 C36 C35 C34 0.2(9) . . . . ?
C39 C34 C35 C36 -0.8(8) . . . . ?
C33 C34 C35 C36 177.6(5) . . . . ?
C24 C25 C26 C27 -0.2(8) . . . . ?
C28 C27 C26 C25 1.3(8) . . . . ?
C13 C18 C17 C16 1.0(9) . . . . ?
C6 N11 C12 C13 177.3(4) . . . . ?
C14 C13 C12 N11 158.4(5) . . . . ?
C18 C13 C12 N11 -26.8(7) . . . . ?
C18 C17 C16 C15 -3.4(9) . . . . ?
C6 C10 C9 C8 18.8(6) . . . . ?
C35 C36 C37 C38 0.2(9) . . . . ?
C35 C34 C39 C38 0.9(9) . . . . ?
C33 C34 C39 C38 -177.4(6) . . . . ?
C30 N31 C32 C33 -125.5(6) . . . . ?
C39 C34 C33 C32 64.1(8) . . . . ?
C35 C34 C33 C32 -114.2(6) . . . . ?
N31 C32 C33 C34 171.4(5) . . . . ?
C10 C9 C8 C7 6.2(6) . . . . ?
C6 C7 C8 C9 -29.1(6) . . . . ?
C34 C39 C38 C37 -0.5(11) . . . . ?
C36 C37 C38 C39 -0.1(10) . . . . ?
C13 C14 C15 C16 -2.6(10) . . . . ?
C17 C16 C15 C14 4.2(9) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ea725_2a
_database_code_depnum_ccdc_archive 'CCDC 1842386'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Kurpiewska'
;Jagiellonian University
Poland
;
_audit_update_record             
;
2018-05-09 deposited with the CCDC.	2020-01-07 downloaded from the CCDC.
;

_audit_creation_date             2018-05-09T16:52:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C32 H37 N7 O'
_chemical_formula_moiety         'C32 H37 N7 O'
_chemical_formula_weight         535.69

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_space_group_name_H-M_alt 'P -1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_cell_setting           triclinic
_space_group_IT_number           2
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.3741(8)
_cell_length_b                   9.3723(12)
_cell_length_c                   24.838(2)
_cell_angle_alpha                83.121(9)
_cell_angle_beta                 85.819(9)
_cell_angle_gamma                79.949(10)
_cell_volume                     1448.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    132(3)
_cell_measurement_reflns_used    2558
_cell_measurement_theta_min      3.6130
_cell_measurement_theta_max      28.0700

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             572
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.077
_oxdiff_exptl_absorpt_empirical_full_min 0.350
_oxdiff_exptl_absorpt_empirical_full_max 1.876
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      132(3)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.3756
_diffrn_reflns_number            8886
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0629
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.1447
_diffrn_reflns_theta_max         28.5240
_diffrn_measured_fraction_theta_max 0.5115
_diffrn_reflns_theta_full        26.3154
_diffrn_measured_fraction_theta_full 0.9858
_reflns_number_total             6321
_reflns_number_gt                4437
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      'calc '
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0070(13)
_refine_ls_number_reflns         6321
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.1622
_refine_ls_wR_factor_gt          0.1458
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.055

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O10 O 0.3226(3) 0.88814(18) 0.80173(7) 0.0333(5) Uani 1 d . . .
N25 N 0.4085(3) 1.3913(2) 0.79573(8) 0.0197(4) Uani 1 d . . .
N19 N 0.1719(3) 1.15126(19) 0.83903(8) 0.0198(4) Uani 1 d . . .
N33 N 0.3993(3) 1.4112(2) 0.64596(8) 0.0245(5) Uani 1 d . . .
N11 N 0.6641(4) 0.9028(2) 0.81767(8) 0.0264(5) Uani 1 d . . .
C6 C 0.3307(4) 1.1332(2) 0.95410(9) 0.0212(5) Uani 1 d . . .
N22 N -0.0923(3) 1.2832(2) 0.79733(9) 0.0288(5) Uani 1 d . . .
N20 N -0.0078(3) 1.1076(2) 0.86263(8) 0.0279(5) Uani 1 d . . .
C23 C 0.1177(4) 1.2578(2) 0.79849(9) 0.0193(5) Uani 1 d . . .
C1 C 0.4905(4) 1.2084(2) 0.96417(9) 0.0229(5) Uani 1 d . . .
H1 H 0.6248 1.1869 0.9469 0.028 Uiso 1 calc R . .
C24 C 0.2703(4) 1.3364(2) 0.76105(9) 0.0181(5) Uani 1 d . . .
C9 C 0.4519(4) 0.9464(2) 0.82139(9) 0.0224(5) Uani 1 d . . .
C32 C 0.2825(4) 1.5227(2) 0.67868(9) 0.0247(6) Uani 1 d . . .
H32A H 0.1965 1.5977 0.6555 0.03 Uiso 1 calc R . .
H32B H 0.3827 1.5679 0.6956 0.03 Uiso 1 calc R . .
C8 C 0.3811(4) 1.0738(2) 0.85579(9) 0.0188(5) Uani 1 d . . .
H8 H 0.4843 1.141 0.8491 0.023 Uiso 1 calc R . .
C31 C 0.1393(4) 1.4539(2) 0.72222(9) 0.0226(5) Uani 1 d . . .
H31A H 0.038 1.4101 0.7051 0.027 Uiso 1 calc R . .
H31B H 0.0594 1.529 0.7429 0.027 Uiso 1 calc R . .
C40 C 0.4637(5) 1.2853(3) 0.54261(10) 0.0309(6) Uani 1 d . . .
H40 H 0.3262 1.2916 0.5585 0.037 Uiso 1 calc R . .
C3 C 0.2527(4) 1.3483(3) 1.02533(10) 0.0291(6) Uani 1 d . . .
H3 H 0.227 1.4199 1.049 0.035 Uiso 1 calc R . .
C5 C 0.1295(4) 1.1680(3) 0.98062(10) 0.0276(6) Uani 1 d . . .
H5 H 0.0203 1.1186 0.9746 0.033 Uiso 1 calc R . .
C26 C 0.3311(4) 1.5258(2) 0.81773(9) 0.0241(6) Uani 1 d . . .
H26 H 0.2972 1.6126 0.7917 0.029 Uiso 1 calc R . .
N21 N -0.1642(4) 1.1885(3) 0.83753(9) 0.0343(6) Uani 1 d . . .
C29 C 0.4096(4) 1.2270(2) 0.72580(9) 0.0209(5) Uani 1 d . . .
H29A H 0.5065 1.1586 0.7487 0.025 Uiso 1 calc R . .
H29B H 0.3185 1.1722 0.71 0.025 Uiso 1 calc R . .
C2 C 0.4537(4) 1.3148(3) 0.99949(10) 0.0260(6) Uani 1 d . . .
H2 H 0.5628 1.3638 1.0059 0.031 Uiso 1 calc R . .
C7 C 0.3753(4) 1.0154(2) 0.91641(9) 0.0224(5) Uani 1 d . . .
H7A H 0.2663 0.9541 0.9234 0.027 Uiso 1 calc R . .
H7B H 0.5114 0.955 0.9245 0.027 Uiso 1 calc R . .
C30 C 0.5383(4) 1.3033(2) 0.68043(10) 0.0243(5) Uani 1 d . . .
H30A H 0.6388 1.3509 0.6962 0.029 Uiso 1 calc R . .
H30B H 0.6191 1.2314 0.6585 0.029 Uiso 1 calc R . .
C4 C 0.0919(4) 1.2750(3) 1.01568(11) 0.0316(6) Uani 1 d . . .
H4 H -0.0425 1.2976 1.0328 0.038 Uiso 1 calc R . .
C35 C 0.6010(4) 1.3698(3) 0.55891(10) 0.0282(6) Uani 1 d . . .
C39 C 0.5278(5) 1.1920(3) 0.50317(11) 0.0362(7) Uani 1 d . . .
H39 H 0.4329 1.137 0.4925 0.043 Uiso 1 calc R . .
C34 C 0.5254(5) 1.4754(3) 0.60037(10) 0.0312(6) Uani 1 d . . .
H34A H 0.648 1.5049 0.6142 0.037 Uiso 1 calc R . .
H34B H 0.4392 1.5619 0.583 0.037 Uiso 1 calc R . .
C13 C 0.7933(4) 0.8503(3) 0.72459(10) 0.0277(6) Uani 1 d . . .
C27 C 0.1982(5) 1.5218(3) 0.87052(10) 0.0323(6) Uani 1 d . . .
H27A H 0.0859 1.604 0.8758 0.039 Uiso 1 calc R . .
H27B H 0.1666 1.4281 0.8869 0.039 Uiso 1 calc R . .
C38 C 0.7334(5) 1.1801(3) 0.47938(11) 0.0410(8) Uani 1 d . . .
H38 H 0.7771 1.1167 0.4531 0.049 Uiso 1 calc R . .
C28 C 0.4249(5) 1.5465(3) 0.86916(10) 0.0346(7) Uani 1 d . . .
H28A H 0.4492 1.6435 0.8737 0.042 Uiso 1 calc R . .
H28B H 0.5299 1.4677 0.8848 0.042 Uiso 1 calc R . .
C36 C 0.8064(5) 1.3571(3) 0.53477(11) 0.0383(7) Uani 1 d . . .
H36 H 0.9013 1.4122 0.5452 0.046 Uiso 1 calc R . .
C16 C 0.8375(5) 0.9713(3) 0.61743(11) 0.0407(8) Uani 1 d . . .
H16 H 0.852 1.0116 0.5816 0.049 Uiso 1 calc R . .
C14 C 0.9676(5) 0.9168(3) 0.70684(11) 0.0373(7) Uani 1 d . . .
H14 H 1.0711 0.9209 0.7309 0.045 Uiso 1 calc R . .
C12 C 0.7661(5) 0.7900(3) 0.78341(10) 0.0340(7) Uani 1 d . . .
H12A H 0.6799 0.7135 0.786 0.041 Uiso 1 calc R . .
H12B H 0.9048 0.747 0.7968 0.041 Uiso 1 calc R . .
C15 C 0.9886(5) 0.9774(3) 0.65316(12) 0.0420(7) Uani 1 d . . .
H15 H 1.1056 1.0222 0.6415 0.05 Uiso 1 calc R . .
C18 C 0.6421(5) 0.8454(3) 0.68789(11) 0.0370(7) Uani 1 d . . .
H18 H 0.5242 0.8011 0.6992 0.044 Uiso 1 calc R . .
C37 C 0.8718(5) 1.2630(3) 0.49513(11) 0.0429(8) Uani 1 d . . .
H37 H 1.0093 1.2562 0.4792 0.051 Uiso 1 calc R . .
C17 C 0.6648(5) 0.9056(4) 0.63462(12) 0.0450(8) Uani 1 d . . .
H17 H 0.5623 0.9015 0.6103 0.054 Uiso 1 calc R . .
H25 H 0.538(5) 1.386(3) 0.7826(12) 0.044(9) Uiso 1 d . . .
H11 H 0.753(5) 0.957(3) 0.8286(12) 0.039(9) Uiso 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O10 C9 1.223(3) . ?
N25 C26 1.429(3) . ?
N25 C24 1.469(3) . ?
N25 H25 0.86(3) . ?
N19 C23 1.349(3) . ?
N19 N20 1.353(3) . ?
N19 C8 1.466(3) . ?
N33 C30 1.460(3) . ?
N33 C32 1.466(3) . ?
N33 C34 1.471(3) . ?
N11 C9 1.342(3) . ?
N11 C12 1.470(3) . ?
N11 H11 0.90(3) . ?
C6 C1 1.388(3) . ?
C6 C5 1.402(3) . ?
C6 C7 1.508(3) . ?
N22 C23 1.320(3) . ?
N22 N21 1.363(3) . ?
N20 N21 1.292(3) . ?
C23 C24 1.519(3) . ?
C1 C2 1.385(3) . ?
C1 H1 0.93 . ?
C24 C31 1.543(3) . ?
C24 C29 1.546(3) . ?
C9 C8 1.537(3) . ?
C32 C31 1.520(3) . ?
C32 H32A 0.97 . ?
C32 H32B 0.97 . ?
C8 C7 1.539(3) . ?
C8 H8 0.98 . ?
C31 H31A 0.97 . ?
C31 H31B 0.97 . ?
C40 C39 1.384(4) . ?
C40 C35 1.388(4) . ?
C40 H40 0.93 . ?
C3 C4 1.378(4) . ?
C3 C2 1.393(4) . ?
C3 H3 0.93 . ?
C5 C4 1.385(4) . ?
C5 H5 0.93 . ?
C26 C28 1.496(3) . ?
C26 C27 1.509(3) . ?
C26 H26 0.98 . ?
C29 C30 1.527(3) . ?
C29 H29A 0.97 . ?
C29 H29B 0.97 . ?
C2 H2 0.93 . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C30 H30A 0.97 . ?
C30 H30B 0.97 . ?
C4 H4 0.93 . ?
C35 C36 1.391(4) . ?
C35 C34 1.510(3) . ?
C39 C38 1.389(4) . ?
C39 H39 0.93 . ?
C34 H34A 0.97 . ?
C34 H34B 0.97 . ?
C13 C18 1.384(4) . ?
C13 C14 1.386(4) . ?
C13 C12 1.511(3) . ?
C27 C28 1.500(4) . ?
C27 H27A 0.97 . ?
C27 H27B 0.97 . ?
C38 C37 1.378(4) . ?
C38 H38 0.93 . ?
C28 H28A 0.97 . ?
C28 H28B 0.97 . ?
C36 C37 1.393(4) . ?
C36 H36 0.93 . ?
C16 C17 1.370(4) . ?
C16 C15 1.369(4) . ?
C16 H16 0.93 . ?
C14 C15 1.392(4) . ?
C14 H14 0.93 . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C15 H15 0.93 . ?
C18 C17 1.383(4) . ?
C18 H18 0.93 . ?
C37 H37 0.93 . ?
C17 H17 0.93 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C26 N25 C24 118.5(2) . . ?
C26 N25 H25 112(2) . . ?
C24 N25 H25 113(2) . . ?
C23 N19 N20 108.8(2) . . ?
C23 N19 C8 131.09(19) . . ?
N20 N19 C8 119.80(18) . . ?
C30 N33 C32 109.47(18) . . ?
C30 N33 C34 110.1(2) . . ?
C32 N33 C34 111.66(18) . . ?
C9 N11 C12 122.4(2) . . ?
C9 N11 H11 120.8(19) . . ?
C12 N11 H11 114.9(19) . . ?
C1 C6 C5 118.2(2) . . ?
C1 C6 C7 120.4(2) . . ?
C5 C6 C7 121.4(2) . . ?
C23 N22 N21 106.0(2) . . ?
N21 N20 N19 105.91(19) . . ?
N22 C23 N19 107.9(2) . . ?
N22 C23 C24 125.8(2) . . ?
N19 C23 C24 126.3(2) . . ?
C2 C1 C6 121.2(2) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
N25 C24 C23 107.08(18) . . ?
N25 C24 C31 115.23(18) . . ?
C23 C24 C31 108.81(19) . . ?
N25 C24 C29 108.96(19) . . ?
C23 C24 C29 109.29(17) . . ?
C31 C24 C29 107.37(18) . . ?
O10 C9 N11 124.5(2) . . ?
O10 C9 C8 121.7(2) . . ?
N11 C9 C8 113.7(2) . . ?
N33 C32 C31 110.00(18) . . ?
N33 C32 H32A 109.7 . . ?
C31 C32 H32A 109.7 . . ?
N33 C32 H32B 109.7 . . ?
C31 C32 H32B 109.7 . . ?
H32A C32 H32B 108.2 . . ?
N19 C8 C9 108.74(19) . . ?
N19 C8 C7 111.85(19) . . ?
C9 C8 C7 109.56(17) . . ?
N19 C8 H8 108.9 . . ?
C9 C8 H8 108.9 . . ?
C7 C8 H8 108.9 . . ?
C32 C31 C24 111.42(19) . . ?
C32 C31 H31A 109.3 . . ?
C24 C31 H31A 109.3 . . ?
C32 C31 H31B 109.3 . . ?
C24 C31 H31B 109.3 . . ?
H31A C31 H31B 108 . . ?
C39 C40 C35 121.2(3) . . ?
C39 C40 H40 119.4 . . ?
C35 C40 H40 119.4 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
N25 C26 C28 116.3(2) . . ?
N25 C26 C27 118.2(2) . . ?
C28 C26 C27 59.91(18) . . ?
N25 C26 H26 116.8 . . ?
C28 C26 H26 116.8 . . ?
C27 C26 H26 116.8 . . ?
N20 N21 N22 111.3(2) . . ?
C30 C29 C24 111.98(18) . . ?
C30 C29 H29A 109.2 . . ?
C24 C29 H29A 109.2 . . ?
C30 C29 H29B 109.2 . . ?
C24 C29 H29B 109.2 . . ?
H29A C29 H29B 107.9 . . ?
C1 C2 C3 119.8(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C6 C7 C8 113.88(18) . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
N33 C30 C29 111.2(2) . . ?
N33 C30 H30A 109.4 . . ?
C29 C30 H30A 109.4 . . ?
N33 C30 H30B 109.4 . . ?
C29 C30 H30B 109.4 . . ?
H30A C30 H30B 108 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C40 C35 C36 118.1(3) . . ?
C40 C35 C34 120.4(2) . . ?
C36 C35 C34 121.5(3) . . ?
C40 C39 C38 120.2(3) . . ?
C40 C39 H39 119.9 . . ?
C38 C39 H39 119.9 . . ?
N33 C34 C35 111.9(2) . . ?
N33 C34 H34A 109.2 . . ?
C35 C34 H34A 109.2 . . ?
N33 C34 H34B 109.2 . . ?
C35 C34 H34B 109.2 . . ?
H34A C34 H34B 107.9 . . ?
C18 C13 C14 118.7(3) . . ?
C18 C13 C12 121.0(3) . . ?
C14 C13 C12 120.2(3) . . ?
C28 C27 C26 59.63(17) . . ?
C28 C27 H27A 117.8 . . ?
C26 C27 H27A 117.8 . . ?
C28 C27 H27B 117.8 . . ?
C26 C27 H27B 117.8 . . ?
H27A C27 H27B 114.9 . . ?
C37 C38 C39 119.3(3) . . ?
C37 C38 H38 120.3 . . ?
C39 C38 H38 120.3 . . ?
C26 C28 C27 60.46(17) . . ?
C26 C28 H28A 117.7 . . ?
C27 C28 H28A 117.7 . . ?
C26 C28 H28B 117.7 . . ?
C27 C28 H28B 117.7 . . ?
H28A C28 H28B 114.8 . . ?
C35 C36 C37 120.9(3) . . ?
C35 C36 H36 119.5 . . ?
C37 C36 H36 119.5 . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
N11 C12 C13 112.12(19) . . ?
N11 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
N11 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C18 C13 120.6(3) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C38 C37 C36 120.2(3) . . ?
C38 C37 H37 119.9 . . ?
C36 C37 H37 119.9 . . ?
C16 C17 C18 120.4(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C23 N19 N20 N21 -1.4(3) . . . . ?
C8 N19 N20 N21 -175.8(2) . . . . ?
N21 N22 C23 N19 -0.8(3) . . . . ?
N21 N22 C23 C24 179.9(2) . . . . ?
N20 N19 C23 N22 1.4(3) . . . . ?
C8 N19 C23 N22 175.0(2) . . . . ?
N20 N19 C23 C24 -179.3(2) . . . . ?
C8 N19 C23 C24 -5.7(4) . . . . ?
C5 C6 C1 C2 0.1(3) . . . . ?
C7 C6 C1 C2 -178.7(2) . . . . ?
C26 N25 C24 C23 -82.7(2) . . . . ?
C26 N25 C24 C31 38.5(3) . . . . ?
C26 N25 C24 C29 159.23(19) . . . . ?
N22 C23 C24 N25 126.6(2) . . . . ?
N19 C23 C24 N25 -52.7(3) . . . . ?
N22 C23 C24 C31 1.4(3) . . . . ?
N19 C23 C24 C31 -177.8(2) . . . . ?
N22 C23 C24 C29 -115.6(3) . . . . ?
N19 C23 C24 C29 65.2(3) . . . . ?
C12 N11 C9 O10 7.7(4) . . . . ?
C12 N11 C9 C8 -175.36(19) . . . . ?
C30 N33 C32 C31 -62.8(3) . . . . ?
C34 N33 C32 C31 175.0(2) . . . . ?
C23 N19 C8 C9 -85.0(3) . . . . ?
N20 N19 C8 C9 88.1(2) . . . . ?
C23 N19 C8 C7 153.9(2) . . . . ?
N20 N19 C8 C7 -33.1(3) . . . . ?
O10 C9 C8 N19 -26.9(3) . . . . ?
N11 C9 C8 N19 156.12(19) . . . . ?
O10 C9 C8 C7 95.6(3) . . . . ?
N11 C9 C8 C7 -81.4(2) . . . . ?
N33 C32 C31 C24 60.8(3) . . . . ?
N25 C24 C31 C32 67.5(2) . . . . ?
C23 C24 C31 C32 -172.26(19) . . . . ?
C29 C24 C31 C32 -54.1(2) . . . . ?
C1 C6 C5 C4 0.3(4) . . . . ?
C7 C6 C5 C4 179.1(2) . . . . ?
C24 N25 C26 C28 154.6(2) . . . . ?
C24 N25 C26 C27 86.3(3) . . . . ?
N19 N20 N21 N22 0.9(3) . . . . ?
C23 N22 N21 N20 -0.1(3) . . . . ?
N25 C24 C29 C30 -73.5(2) . . . . ?
C23 C24 C29 C30 169.8(2) . . . . ?
C31 C24 C29 C30 52.0(3) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
C4 C3 C2 C1 0.2(4) . . . . ?
C1 C6 C7 C8 -77.5(3) . . . . ?
C5 C6 C7 C8 103.7(3) . . . . ?
N19 C8 C7 C6 -65.6(3) . . . . ?
C9 C8 C7 C6 173.7(2) . . . . ?
C32 N33 C30 C29 61.0(3) . . . . ?
C34 N33 C30 C29 -175.9(2) . . . . ?
C24 C29 C30 N33 -56.9(3) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C6 C5 C4 C3 -0.5(4) . . . . ?
C39 C40 C35 C36 -0.5(4) . . . . ?
C39 C40 C35 C34 177.5(2) . . . . ?
C35 C40 C39 C38 0.6(4) . . . . ?
C30 N33 C34 C35 72.4(3) . . . . ?
C32 N33 C34 C35 -165.7(2) . . . . ?
C40 C35 C34 N33 43.6(3) . . . . ?
C36 C35 C34 N33 -138.4(3) . . . . ?
N25 C26 C27 C28 105.6(3) . . . . ?
C40 C39 C38 C37 -0.6(4) . . . . ?
N25 C26 C28 C27 -108.9(2) . . . . ?
C40 C35 C36 C37 0.4(4) . . . . ?
C34 C35 C36 C37 -177.6(2) . . . . ?
C18 C13 C14 C15 0.2(4) . . . . ?
C12 C13 C14 C15 -177.5(2) . . . . ?
C9 N11 C12 C13 81.7(3) . . . . ?
C18 C13 C12 N11 -94.0(3) . . . . ?
C14 C13 C12 N11 83.7(3) . . . . ?
C17 C16 C15 C14 0.2(4) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
C14 C13 C18 C17 0.0(4) . . . . ?
C12 C13 C18 C17 177.7(2) . . . . ?
C39 C38 C37 C36 0.4(4) . . . . ?
C35 C36 C37 C38 -0.3(4) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C13 C18 C17 C16 -0.1(4) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ig015_f56
_database_code_depnum_ccdc_archive 'CCDC 1844788'
loop_
_audit_author_name
_audit_author_address
'Justyna Kalinowska-Tluscik'
;Jagiellonian University
Poland
;
_audit_update_record             
;
2018-05-22 deposited with the CCDC.	2020-01-07 downloaded from the CCDC.
;

_audit_creation_date             2018-05-22T21:55:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C33 H33 Cl N6 O'
_chemical_formula_moiety         'C33 H33 Cl N6 O'
_chemical_formula_weight         565.1

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.0985(3)
_cell_length_b                   10.3538(3)
_cell_length_c                   30.3383(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.525(3)
_cell_angle_gamma                90
_cell_volume                     2833.38(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    7127
_cell_measurement_theta_min      2.9891
_cell_measurement_theta_max      30.2597

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             1192

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.808
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.991

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_ub_11      -0.0036613
_diffrn_orient_matrix_ub_12      0.0171943
_diffrn_orient_matrix_ub_13      -0.0227443
_diffrn_orient_matrix_ub_21      -0.0046189
_diffrn_orient_matrix_ub_22      -0.0662618
_diffrn_orient_matrix_ub_23      -0.0059941
_diffrn_orient_matrix_ub_31      -0.0783765
_diffrn_orient_matrix_ub_32      0.00311
_diffrn_orient_matrix_ub_33      -0.0016556
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0784
_diffrn_reflns_av_unetI/netI     0.0765
_diffrn_reflns_number            27066
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.995
_diffrn_reflns_theta_max         30.327
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.935
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.935
_reflns_Friedel_coverage         0
_reflns_number_total             7892
_reflns_number_gt                7033
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7892
_refine_ls_number_parameters     379
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1223
_refine_ls_R_factor_gt           0.113
_refine_ls_wR_factor_ref         0.3461
_refine_ls_wR_factor_gt          0.3278
_refine_ls_goodness_of_fit_ref   1.439
_refine_ls_restrained_S_all      1.439
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.118

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl13 Cl 0.44698(15) 0.50057(13) 0.29734(4) 0.0374(3) Uani 1 1 d . . . . .
N4 N 0.3984(4) -0.0261(3) 0.55220(11) 0.0203(7) Uani 1 1 d . . . . .
N3 N 0.5373(4) -0.0635(3) 0.54739(12) 0.0209(7) Uani 1 1 d . . . . .
N1 N 0.5517(3) 0.1309(3) 0.56791(11) 0.0174(6) Uani 1 1 d . . . . .
O7 O 0.7767(4) 0.4184(3) 0.55844(11) 0.0296(7) Uani 1 1 d . . . . .
N2 N 0.6312(4) 0.0287(4) 0.55695(12) 0.0233(7) Uani 1 1 d . . . . .
C39 C 0.4384(4) 0.1570(4) 0.68064(13) 0.0202(7) Uani 1 1 d . . . . .
H39 H 0.3931 0.2376 0.6854 0.024 Uiso 1 1 calc R U . . .
C35 C 0.4216(4) -0.0631(4) 0.65606(13) 0.0196(7) Uani 1 1 d . . . . .
H35 H 0.3642 -0.1341 0.6437 0.024 Uiso 1 1 calc R U . . .
C23 C 0.0276(5) 0.2771(4) 0.64066(14) 0.0211(7) Uani 1 1 d . . . . .
H23 H 0.0186 0.2745 0.6091 0.025 Uiso 1 1 calc R U . . .
N20 N 0.1694(4) 0.0919(3) 0.59456(11) 0.0169(6) Uani 1 1 d . . . . .
C30 C -0.1150(4) -0.1909(4) 0.62850(14) 0.0223(8) Uani 1 1 d . . . . .
H30 H -0.1967 -0.214 0.6072 0.027 Uiso 1 1 calc R U . . .
C22 C 0.1136(4) 0.1846(4) 0.66542(13) 0.0177(7) Uani 1 1 d . . . . .
C34 C 0.3517(4) 0.0546(4) 0.66225(12) 0.0171(7) Uani 1 1 d . . . . .
C32 C 0.0359(5) -0.2268(4) 0.69837(14) 0.0239(8) Uani 1 1 d . . . . .
H32 H 0.0572 -0.2739 0.7253 0.029 Uiso 1 1 calc R U . . .
C29 C -0.0289(4) -0.0847(4) 0.62073(13) 0.0201(7) Uani 1 1 d . . . . .
H29 H -0.0525 -0.0357 0.5943 0.024 Uiso 1 1 calc R U . . .
C21 C 0.1856(4) 0.0718(4) 0.64360(12) 0.0158(7) Uani 1 1 d . . . . .
C33 C 0.1235(4) -0.1218(4) 0.69057(14) 0.0215(8) Uani 1 1 d . . . . .
H33 H 0.2053 -0.0992 0.7119 0.026 Uiso 1 1 calc R U . . .
C27 C 0.1231(5) 0.1910(4) 0.71202(13) 0.0231(8) Uani 1 1 d . . . . .
H27 H 0.1815 0.1293 0.7296 0.028 Uiso 1 1 calc R U . . .
C16 C 0.2769(4) 0.1745(4) 0.57639(12) 0.0166(7) Uani 1 1 d . . . . .
H16 H 0.3127 0.2413 0.5991 0.02 Uiso 1 1 calc R U . . .
C24 C -0.0455(5) 0.3734(5) 0.66147(16) 0.0276(9) Uani 1 1 d . . . . .
H24 H -0.1034 0.4358 0.644 0.033 Uiso 1 1 calc R U . . .
C25 C -0.0343(5) 0.3786(4) 0.70758(16) 0.0269(9) Uani 1 1 d . . . . .
H25 H -0.0829 0.445 0.7217 0.032 Uiso 1 1 calc R U . . .
C10 C 0.6943(5) 0.3682(4) 0.42838(14) 0.0228(8) Uani 1 1 d . . . . .
C15 C 0.5433(5) 0.3814(4) 0.42370(15) 0.0258(8) Uani 1 1 d . . . . .
H15 H 0.4908 0.3628 0.448 0.031 Uiso 1 1 calc R U . . .
C5 C 0.4090(4) 0.0968(4) 0.56564(12) 0.0171(7) Uani 1 1 d . . . . .
C13 C 0.5436(5) 0.4506(4) 0.34821(14) 0.0248(8) Uani 1 1 d . . . . .
C36 C 0.5739(5) -0.0783(4) 0.66776(14) 0.0232(8) Uani 1 1 d . . . . .
H36 H 0.6195 -0.1591 0.6635 0.028 Uiso 1 1 calc R U . . .
C18 C 0.1195(5) 0.1480(5) 0.50103(14) 0.0263(8) Uani 1 1 d . . . . .
H18A H 0.0849 0.1922 0.473 0.039 Uiso 1 1 calc R U . . .
H18B H 0.0345 0.1106 0.5133 0.039 Uiso 1 1 calc R U . . .
H18C H 0.1887 0.0791 0.4955 0.039 Uiso 1 1 calc R U . . .
C7 C 0.7078(4) 0.3208(4) 0.54638(14) 0.0212(7) Uani 1 1 d . . . . .
C17 C 0.1977(4) 0.2443(4) 0.53403(14) 0.0199(7) Uani 1 1 d . . . . .
H17 H 0.1211 0.3037 0.5436 0.024 Uiso 1 1 calc R U . . .
C37 C 0.6594(5) 0.0254(4) 0.68580(15) 0.0248(8) Uani 1 1 d . . . . .
H37 H 0.7634 0.016 0.6936 0.03 Uiso 1 1 calc R U . . .
C14 C 0.4659(5) 0.4224(4) 0.38296(15) 0.0236(8) Uani 1 1 d . . . . .
H14 H 0.361 0.4305 0.3795 0.028 Uiso 1 1 calc R U . . .
C9 C 0.7841(5) 0.3234(5) 0.47160(16) 0.0303(10) Uani 1 1 d . . . . .
H9A H 0.8549 0.2564 0.4644 0.036 Uiso 1 1 calc R U . . .
H9B H 0.8428 0.3975 0.4849 0.036 Uiso 1 1 calc R U . . .
C26 C 0.0488(5) 0.2858(5) 0.73277(15) 0.0269(9) Uani 1 1 d . . . . .
H26 H 0.0548 0.2871 0.7643 0.032 Uiso 1 1 calc R U . . .
C12 C 0.6949(6) 0.4423(5) 0.35253(17) 0.0320(10) Uani 1 1 d . . . . .
H12 H 0.7471 0.4643 0.3284 0.038 Uiso 1 1 calc R U . . .
C28 C 0.0931(4) -0.0489(4) 0.65177(12) 0.0155(6) Uani 1 1 d . . . . .
C6 C 0.6303(5) 0.2511(4) 0.58148(14) 0.0237(8) Uani 1 1 d . . . . .
H6A H 0.7057 0.2316 0.6072 0.028 Uiso 1 1 calc R U . . .
H6B H 0.5582 0.3118 0.592 0.028 Uiso 1 1 calc R U . . .
N8 N 0.6979(4) 0.2709(4) 0.50494(13) 0.0260(8) Uani 1 1 d D . . . .
C31 C -0.0832(5) -0.2643(4) 0.66721(15) 0.0237(8) Uani 1 1 d . . . . .
H31 H -0.1412 -0.3379 0.6722 0.028 Uiso 1 1 calc R U . . .
C19 C 0.3064(5) 0.3252(5) 0.51150(16) 0.0283(9) Uani 1 1 d . . . . .
H19A H 0.3759 0.2681 0.4988 0.042 Uiso 1 1 calc R U . . .
H19B H 0.3616 0.3827 0.5334 0.042 Uiso 1 1 calc R U . . .
H19C H 0.2517 0.377 0.4877 0.042 Uiso 1 1 calc R U . . .
C38 C 0.5913(5) 0.1425(5) 0.69218(15) 0.0255(8) Uani 1 1 d . . . . .
H38 H 0.649 0.2134 0.7045 0.031 Uiso 1 1 calc R U . . .
C11 C 0.7724(5) 0.4003(5) 0.39350(17) 0.0312(10) Uani 1 1 d . . . . .
H11 H 0.8775 0.3941 0.3972 0.037 Uiso 1 1 calc R U . . .
H8 H 0.629(6) 0.207(5) 0.495(2) 0.037 Uiso 1 1 d D U . . .
H20 H 0.190(8) 0.004(7) 0.584(2) 0.037 Uiso 1 1 d . U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl13 C13 1.751(5) . ?
N4 C5 1.336(5) . ?
N4 N3 1.348(5) . ?
N3 N2 1.289(5) . ?
N1 C5 1.338(5) . ?
N1 N2 1.347(4) . ?
N1 C6 1.468(5) . ?
O7 C7 1.220(5) . ?
C39 C34 1.395(5) . ?
C39 C38 1.397(6) . ?
C39 H39 0.95 . ?
C35 C36 1.394(6) . ?
C35 C34 1.399(5) . ?
C35 H35 0.95 . ?
C23 C22 1.392(5) . ?
C23 C24 1.395(6) . ?
C23 H23 0.95 . ?
N20 C16 1.460(5) . ?
N20 C21 1.490(5) . ?
N20 H20 1.00(7) . ?
C30 C29 1.388(6) . ?
C30 C31 1.397(6) . ?
C30 H30 0.95 . ?
C22 C27 1.407(5) . ?
C22 C21 1.532(5) . ?
C34 C21 1.552(5) . ?
C32 C33 1.386(6) . ?
C32 C31 1.397(6) . ?
C32 H32 0.95 . ?
C29 C28 1.408(5) . ?
C29 H29 0.95 . ?
C21 C28 1.545(5) . ?
C33 C28 1.395(5) . ?
C33 H33 0.95 . ?
C27 C26 1.389(6) . ?
C27 H27 0.95 . ?
C16 C5 1.517(5) . ?
C16 C17 1.566(5) . ?
C16 H16 1 . ?
C24 C25 1.390(7) . ?
C24 H24 0.95 . ?
C25 C26 1.388(7) . ?
C25 H25 0.95 . ?
C10 C15 1.369(6) . ?
C10 C11 1.390(6) . ?
C10 C9 1.524(6) . ?
C15 C14 1.406(6) . ?
C15 H15 0.95 . ?
C13 C12 1.369(7) . ?
C13 C14 1.375(6) . ?
C36 C37 1.395(6) . ?
C36 H36 0.95 . ?
C18 C17 1.522(6) . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C7 N8 1.351(6) . ?
C7 C6 1.532(6) . ?
C17 C19 1.525(6) . ?
C17 H17 1 . ?
C37 C38 1.386(6) . ?
C37 H37 0.95 . ?
C14 H14 0.95 . ?
C9 N8 1.463(6) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C26 H26 0.95 . ?
C12 C11 1.415(7) . ?
C12 H12 0.95 . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
N8 H8 0.93(2) . ?
C31 H31 0.95 . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C38 H38 0.95 . ?
C11 H11 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N4 N3 106.0(3) . . ?
N2 N3 N4 111.5(3) . . ?
C5 N1 N2 109.2(3) . . ?
C5 N1 C6 132.2(3) . . ?
N2 N1 C6 118.5(3) . . ?
N3 N2 N1 106.0(3) . . ?
C34 C39 C38 120.7(4) . . ?
C34 C39 H39 119.6 . . ?
C38 C39 H39 119.6 . . ?
C36 C35 C34 121.3(4) . . ?
C36 C35 H35 119.4 . . ?
C34 C35 H35 119.4 . . ?
C22 C23 C24 121.0(4) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C16 N20 C21 118.3(3) . . ?
C16 N20 H20 104(4) . . ?
C21 N20 H20 102(4) . . ?
C29 C30 C31 121.0(4) . . ?
C29 C30 H30 119.5 . . ?
C31 C30 H30 119.5 . . ?
C23 C22 C27 117.8(4) . . ?
C23 C22 C21 122.2(3) . . ?
C27 C22 C21 119.8(4) . . ?
C39 C34 C35 118.2(3) . . ?
C39 C34 C21 122.1(3) . . ?
C35 C34 C21 119.3(4) . . ?
C33 C32 C31 121.0(4) . . ?
C33 C32 H32 119.5 . . ?
C31 C32 H32 119.5 . . ?
C30 C29 C28 120.5(4) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
N20 C21 C22 109.4(3) . . ?
N20 C21 C28 106.7(3) . . ?
C22 C21 C28 105.9(3) . . ?
N20 C21 C34 110.1(3) . . ?
C22 C21 C34 112.4(3) . . ?
C28 C21 C34 112.0(3) . . ?
C32 C33 C28 120.9(4) . . ?
C32 C33 H33 119.6 . . ?
C28 C33 H33 119.6 . . ?
C26 C27 C22 121.3(4) . . ?
C26 C27 H27 119.3 . . ?
C22 C27 H27 119.3 . . ?
N20 C16 C5 111.1(3) . . ?
N20 C16 C17 108.8(3) . . ?
C5 C16 C17 111.1(3) . . ?
N20 C16 H16 108.6 . . ?
C5 C16 H16 108.6 . . ?
C17 C16 H16 108.6 . . ?
C25 C24 C23 120.4(4) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C26 C25 C24 119.3(4) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C15 C10 C11 120.2(4) . . ?
C15 C10 C9 122.5(4) . . ?
C11 C10 C9 117.3(4) . . ?
C10 C15 C14 120.1(4) . . ?
C10 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
N4 C5 N1 107.3(3) . . ?
N4 C5 C16 122.9(3) . . ?
N1 C5 C16 129.8(4) . . ?
C12 C13 C14 121.6(4) . . ?
C12 C13 Cl13 119.0(3) . . ?
C14 C13 Cl13 119.3(4) . . ?
C35 C36 C37 119.8(4) . . ?
C35 C36 H36 120.1 . . ?
C37 C36 H36 120.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O7 C7 N8 124.4(4) . . ?
O7 C7 C6 116.5(4) . . ?
N8 C7 C6 119.1(4) . . ?
C18 C17 C19 109.9(4) . . ?
C18 C17 C16 111.2(3) . . ?
C19 C17 C16 111.5(3) . . ?
C18 C17 H17 108 . . ?
C19 C17 H17 108 . . ?
C16 C17 H17 108 . . ?
C38 C37 C36 119.5(4) . . ?
C38 C37 H37 120.3 . . ?
C36 C37 H37 120.3 . . ?
C13 C14 C15 119.3(4) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
N8 C9 C10 115.6(4) . . ?
N8 C9 H9A 108.4 . . ?
C10 C9 H9A 108.4 . . ?
N8 C9 H9B 108.4 . . ?
C10 C9 H9B 108.4 . . ?
H9A C9 H9B 107.4 . . ?
C25 C26 C27 120.1(4) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C13 C12 C11 118.9(4) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C33 C28 C29 118.3(4) . . ?
C33 C28 C21 121.4(3) . . ?
C29 C28 C21 120.3(3) . . ?
N1 C6 C7 117.1(3) . . ?
N1 C6 H6A 108 . . ?
C7 C6 H6A 108 . . ?
N1 C6 H6B 108 . . ?
C7 C6 H6B 108 . . ?
H6A C6 H6B 107.3 . . ?
C7 N8 C9 121.7(4) . . ?
C7 N8 H8 122(4) . . ?
C9 N8 H8 116(4) . . ?
C32 C31 C30 118.3(4) . . ?
C32 C31 H31 120.8 . . ?
C30 C31 H31 120.8 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C37 C38 C39 120.5(4) . . ?
C37 C38 H38 119.7 . . ?
C39 C38 H38 119.7 . . ?
C10 C11 C12 119.8(4) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_new_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1844787'
loop_
_audit_author_name
_audit_author_address
'Justyna Kalinowska-Tluscik'
;Jagiellonian University
Poland
;
_audit_update_record             
;
2018-05-22 deposited with the CCDC.	2020-01-07 downloaded from the CCDC.
;

_audit_creation_date             2018-02-20T20:19:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C30 H32 Cl N7 O'
_chemical_formula_moiety         'C30 H32 Cl N7 O'
_chemical_formula_weight         542.07

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.8002(3)
_cell_length_b                   15.1210(5)
_cell_length_c                   19.4804(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.374(3)
_cell_angle_gamma                90
_cell_volume                     2886.72(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    10632
_cell_measurement_theta_min      4.534
_cell_measurement_theta_max      71.182

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.4
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_F_000             1144

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.15188
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.476
_shelx_estimated_absorpt_T_max   0.594

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_ambient_temperature      130(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0124811
_diffrn_orient_matrix_ub_12      -0.0616891
_diffrn_orient_matrix_ub_13      0.0626747
_diffrn_orient_matrix_ub_21      0.0085595
_diffrn_orient_matrix_ub_22      -0.0805177
_diffrn_orient_matrix_ub_23      -0.0481414
_diffrn_orient_matrix_ub_31      0.1565604
_diffrn_orient_matrix_ub_32      0.0093591
_diffrn_orient_matrix_ub_33      -0.0018462
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_number            18364
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.7
_diffrn_reflns_theta_max         71.916
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.984
_reflns_Friedel_coverage         0
_reflns_number_total             5568
_reflns_number_gt                4950
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0717P)²+0.8336P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0028(2)
_refine_ls_number_reflns         5568
_refine_ls_number_parameters     367
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.127
_refine_ls_wR_factor_gt          0.1221
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.047

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl36 Cl 0.09059(5) 0.27131(4) 0.64509(2) 0.05309(17) Uani 1 1 d . . . . .
O18 O 0.92435(11) 0.32151(8) 0.24606(6) 0.0359(3) Uani 1 1 d . . . . .
N1 N 0.72375(12) 0.34837(8) 0.38689(6) 0.0243(3) Uani 1 1 d . . . . .
N19 N 0.84415(15) 0.20686(10) 0.31040(7) 0.0342(3) Uani 1 1 d . . . . .
N4 N 0.67493(13) 0.34972(9) 0.49491(6) 0.0288(3) Uani 1 1 d . . . . .
N2 N 0.82494(13) 0.39352(9) 0.41805(7) 0.0303(3) Uani 1 1 d . . . . .
N29 N 0.56394(13) 0.17992(8) 0.39583(7) 0.0263(3) Uani 1 1 d . . . . .
N3 N 0.79520(14) 0.39358(9) 0.48298(7) 0.0331(3) Uani 1 1 d . . . . .
C33 C 0.40533(15) 0.26673(9) 0.47544(7) 0.0246(3) Uani 1 1 d . . . . .
C34 C 0.28748(16) 0.31651(10) 0.46867(8) 0.0290(3) Uani 1 1 d . . . . .
H34 H 0.2729 0.3501 0.428 0.035 Uiso 1 1 calc R U . . .
N10 N 0.45496(15) 0.56535(9) 0.38241(7) 0.0340(3) Uani 1 1 d . . . . .
C17 C 0.84097(15) 0.28915(11) 0.28554(7) 0.0278(3) Uani 1 1 d . . . . .
C28 C 0.51042(15) 0.26659(9) 0.41786(7) 0.0243(3) Uani 1 1 d . . . . .
H28 H 0.4651 0.2937 0.3768 0.029 Uiso 1 1 calc R U . . .
C5 C 0.63305(15) 0.32241(9) 0.43414(7) 0.0238(3) Uani 1 1 d . . . . .
C36 C 0.21234(17) 0.26895(11) 0.57913(8) 0.0330(4) Uani 1 1 d . . . . .
C8 C 0.58315(16) 0.48096(10) 0.31258(7) 0.0279(3) Uani 1 1 d . . . . .
C16 C 0.44173(16) 0.46056(10) 0.30103(7) 0.0263(3) Uani 1 1 d . . . . .
C6 C 0.71746(15) 0.34215(10) 0.31167(7) 0.0250(3) Uani 1 1 d . . . . .
H6 H 0.6331 0.3084 0.2992 0.03 Uiso 1 1 calc R U . . .
C9 C 0.58527(17) 0.54413(11) 0.36269(8) 0.0329(3) Uani 1 1 d . . . . .
H9 H 0.6658 0.5699 0.3813 0.04 Uiso 1 1 calc R U . . .
C7 C 0.70373(15) 0.43506(10) 0.28141(8) 0.0292(3) Uani 1 1 d . . . . .
H7A H 0.7878 0.4694 0.291 0.035 Uiso 1 1 calc R U . . .
H7B H 0.6915 0.4312 0.231 0.035 Uiso 1 1 calc R U . . .
C35 C 0.18951(16) 0.31835(11) 0.52049(8) 0.0327(3) Uani 1 1 d . . . . .
H35 H 0.109 0.3528 0.5155 0.039 Uiso 1 1 calc R U . . .
C38 C 0.42541(16) 0.21858(11) 0.53557(8) 0.0300(3) Uani 1 1 d . . . . .
H38 H 0.5064 0.1847 0.5412 0.036 Uiso 1 1 calc R U . . .
C12 C 0.22272(17) 0.50913(11) 0.35094(8) 0.0318(3) Uani 1 1 d . . . . .
H12 H 0.1729 0.5455 0.3817 0.038 Uiso 1 1 calc R U . . .
C14 C 0.23193(17) 0.39615(11) 0.26244(9) 0.0349(4) Uani 1 1 d . . . . .
H14 H 0.1839 0.3558 0.2338 0.042 Uiso 1 1 calc R U . . .
C13 C 0.15846(17) 0.44885(11) 0.30880(9) 0.0344(4) Uani 1 1 d . . . . .
H13 H 0.0621 0.4427 0.3111 0.041 Uiso 1 1 calc R U . . .
C15 C 0.37243(17) 0.40165(10) 0.25753(8) 0.0301(3) Uani 1 1 d . . . . .
H15 H 0.4208 0.3664 0.2255 0.036 Uiso 1 1 calc R U . . .
C23 C 0.90720(18) 0.16853(12) 0.48023(10) 0.0399(4) Uani 1 1 d . . . . .
H23 H 0.9408 0.2274 0.4787 0.048 Uiso 1 1 calc R U . . .
C11 C 0.36457(16) 0.51423(10) 0.34637(7) 0.0285(3) Uani 1 1 d . . . . .
C37 C 0.32860(18) 0.21929(11) 0.58768(8) 0.0345(4) Uani 1 1 d . . . . .
H37 H 0.3428 0.186 0.6284 0.041 Uiso 1 1 calc R U . . .
C30 C 0.46062(16) 0.11781(10) 0.36889(8) 0.0284(3) Uani 1 1 d . . . . .
H30 H 0.3865 0.1107 0.4035 0.034 Uiso 1 1 calc R U . . .
C22 C 0.94427(17) 0.10936(12) 0.42886(10) 0.0384(4) Uani 1 1 d . . . . .
C31 C 0.4000(2) 0.15294(13) 0.30282(9) 0.0443(4) Uani 1 1 d . . . . .
H31A H 0.3509 0.2081 0.3121 0.066 Uiso 1 1 calc R U . . .
H31B H 0.3365 0.1092 0.2836 0.066 Uiso 1 1 calc R U . . .
H31C H 0.4731 0.1643 0.2699 0.066 Uiso 1 1 calc R U . . .
C32 C 0.52979(19) 0.02922(12) 0.35771(11) 0.0450(4) Uani 1 1 d . . . . .
H32A H 0.6056 0.0365 0.3257 0.068 Uiso 1 1 calc R U . . .
H32B H 0.4637 -0.0129 0.3386 0.068 Uiso 1 1 calc R U . . .
H32C H 0.5647 0.0068 0.4016 0.068 Uiso 1 1 calc R U . . .
C27 C 0.89108(19) 0.02343(13) 0.43240(11) 0.0462(5) Uani 1 1 d . . . . .
H27 H 0.9135 -0.0184 0.3979 0.055 Uiso 1 1 calc R U . . .
C21 C 1.03649(19) 0.13748(15) 0.37086(11) 0.0475(5) Uani 1 1 d . . . . .
H21A H 1.11 0.0932 0.3655 0.057 Uiso 1 1 calc R U . . .
H21B H 1.0796 0.1947 0.3827 0.057 Uiso 1 1 calc R U . . .
C24 C 0.82178(19) 0.14345(14) 0.53393(10) 0.0453(4) Uani 1 1 d . . . . .
H24 H 0.7985 0.185 0.5685 0.054 Uiso 1 1 calc R U . . .
C20 C 0.9600(2) 0.14696(13) 0.30335(10) 0.0441(4) Uani 1 1 d . . . . .
H20A H 1.0226 0.17 0.2679 0.053 Uiso 1 1 calc R U . . .
H20B H 0.9271 0.0882 0.2881 0.053 Uiso 1 1 calc R U . . .
C26 C 0.8054(2) -0.00131(14) 0.48614(12) 0.0501(5) Uani 1 1 d . . . . .
H26 H 0.7703 -0.0598 0.4878 0.06 Uiso 1 1 calc R U . . .
C25 C 0.7712(2) 0.05842(14) 0.53681(11) 0.0493(5) Uani 1 1 d . . . . .
H25 H 0.7133 0.0411 0.5734 0.059 Uiso 1 1 calc R U . . .
H19 H 0.771(2) 0.1901(15) 0.3365(12) 0.050(6) Uiso 1 1 d . . . . .
H29 H 0.605(2) 0.1559(14) 0.4312(11) 0.040(5) Uiso 1 1 d . . . . .
H10 H 0.429(2) 0.5991(15) 0.4138(11) 0.044(6) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl36 C36 1.7595(16) . ?
O18 C17 1.2274(19) . ?
N1 C5 1.3423(19) . ?
N1 N2 1.3454(17) . ?
N1 C6 1.4693(17) . ?
N19 C17 1.336(2) . ?
N19 C20 1.459(2) . ?
N19 H19 0.92(2) . ?
N4 C5 1.3168(18) . ?
N4 N3 1.3735(19) . ?
N2 N3 1.2999(19) . ?
N29 C30 1.4751(19) . ?
N29 C28 1.4765(19) . ?
N29 H29 0.88(2) . ?
C33 C34 1.384(2) . ?
C33 C38 1.392(2) . ?
C33 C28 1.528(2) . ?
C34 C35 1.398(2) . ?
C34 H34 0.95 . ?
N10 C11 1.366(2) . ?
N10 C9 1.374(2) . ?
N10 H10 0.84(2) . ?
C17 C6 1.541(2) . ?
C28 C5 1.5009(19) . ?
C28 H28 1 . ?
C36 C37 1.374(3) . ?
C36 C35 1.382(2) . ?
C8 C9 1.366(2) . ?
C8 C16 1.436(2) . ?
C8 C7 1.502(2) . ?
C16 C15 1.402(2) . ?
C16 C11 1.421(2) . ?
C6 C7 1.529(2) . ?
C6 H6 1 . ?
C9 H9 0.95 . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C35 H35 0.95 . ?
C38 C37 1.394(2) . ?
C38 H38 0.95 . ?
C12 C13 1.376(2) . ?
C12 C11 1.396(2) . ?
C12 H12 0.95 . ?
C14 C15 1.383(2) . ?
C14 C13 1.406(2) . ?
C14 H14 0.95 . ?
C13 H13 0.95 . ?
C15 H15 0.95 . ?
C23 C22 1.392(3) . ?
C23 C24 1.397(3) . ?
C23 H23 0.95 . ?
C37 H37 0.95 . ?
C30 C31 1.511(2) . ?
C30 C32 1.518(2) . ?
C30 H30 1 . ?
C22 C27 1.402(3) . ?
C22 C21 1.512(3) . ?
C31 H31A 0.98 . ?
C31 H31B 0.98 . ?
C31 H31C 0.98 . ?
C32 H32A 0.98 . ?
C32 H32B 0.98 . ?
C32 H32C 0.98 . ?
C27 C26 1.397(3) . ?
C27 H27 0.95 . ?
C21 C20 1.516(3) . ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?
C24 C25 1.379(3) . ?
C24 H24 0.95 . ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?
C26 C25 1.381(3) . ?
C26 H26 0.95 . ?
C25 H25 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 N2 109.17(11) . . ?
C5 N1 C6 129.90(12) . . ?
N2 N1 C6 120.56(12) . . ?
C17 N19 C20 124.08(15) . . ?
C17 N19 H19 116.2(14) . . ?
C20 N19 H19 119.5(14) . . ?
C5 N4 N3 105.19(12) . . ?
N3 N2 N1 105.67(12) . . ?
C30 N29 C28 115.10(12) . . ?
C30 N29 H29 109.1(14) . . ?
C28 N29 H29 107.7(14) . . ?
N2 N3 N4 111.24(12) . . ?
C34 C33 C38 118.55(14) . . ?
C34 C33 C28 119.79(13) . . ?
C38 C33 C28 121.66(14) . . ?
C33 C34 C35 121.25(14) . . ?
C33 C34 H34 119.4 . . ?
C35 C34 H34 119.4 . . ?
C11 N10 C9 108.95(13) . . ?
C11 N10 H10 121.3(15) . . ?
C9 N10 H10 129.4(15) . . ?
O18 C17 N19 125.77(15) . . ?
O18 C17 C6 121.82(15) . . ?
N19 C17 C6 112.41(13) . . ?
N29 C28 C5 105.97(12) . . ?
N29 C28 C33 117.20(12) . . ?
C5 C28 C33 112.75(11) . . ?
N29 C28 H28 106.8 . . ?
C5 C28 H28 106.8 . . ?
C33 C28 H28 106.8 . . ?
N4 C5 N1 108.71(12) . . ?
N4 C5 C28 127.65(13) . . ?
N1 C5 C28 123.53(12) . . ?
C37 C36 C35 121.69(15) . . ?
C37 C36 Cl36 119.24(13) . . ?
C35 C36 Cl36 119.06(13) . . ?
C9 C8 C16 105.80(14) . . ?
C9 C8 C7 127.14(15) . . ?
C16 C8 C7 126.76(13) . . ?
C15 C16 C11 118.75(14) . . ?
C15 C16 C8 133.98(15) . . ?
C11 C16 C8 107.27(13) . . ?
N1 C6 C7 109.18(12) . . ?
N1 C6 C17 109.56(12) . . ?
C7 C6 C17 114.70(12) . . ?
N1 C6 H6 107.7 . . ?
C7 C6 H6 107.7 . . ?
C17 C6 H6 107.7 . . ?
C8 C9 N10 110.70(14) . . ?
C8 C9 H9 124.7 . . ?
N10 C9 H9 124.7 . . ?
C8 C7 C6 109.64(12) . . ?
C8 C7 H7A 109.7 . . ?
C6 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C36 C35 C34 118.54(15) . . ?
C36 C35 H35 120.7 . . ?
C34 C35 H35 120.7 . . ?
C33 C38 C37 121.03(15) . . ?
C33 C38 H38 119.5 . . ?
C37 C38 H38 119.5 . . ?
C13 C12 C11 116.78(15) . . ?
C13 C12 H12 121.6 . . ?
C11 C12 H12 121.6 . . ?
C15 C14 C13 121.63(15) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C12 C13 C14 121.61(15) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C14 C15 C16 118.35(15) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C22 C23 C24 121.62(18) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
N10 C11 C12 129.88(14) . . ?
N10 C11 C16 107.25(14) . . ?
C12 C11 C16 122.84(14) . . ?
C36 C37 C38 118.93(15) . . ?
C36 C37 H37 120.5 . . ?
C38 C37 H37 120.5 . . ?
N29 C30 C31 110.16(13) . . ?
N29 C30 C32 107.86(13) . . ?
C31 C30 C32 111.21(14) . . ?
N29 C30 H30 109.2 . . ?
C31 C30 H30 109.2 . . ?
C32 C30 H30 109.2 . . ?
C23 C22 C27 117.48(18) . . ?
C23 C22 C21 121.08(17) . . ?
C27 C22 C21 121.43(18) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C26 C27 C22 120.70(19) . . ?
C26 C27 H27 119.6 . . ?
C22 C27 H27 119.6 . . ?
C22 C21 C20 112.33(16) . . ?
C22 C21 H21A 109.1 . . ?
C20 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
C20 C21 H21B 109.1 . . ?
H21A C21 H21B 107.9 . . ?
C25 C24 C23 120.1(2) . . ?
C25 C24 H24 120 . . ?
C23 C24 H24 120 . . ?
N19 C20 C21 110.95(15) . . ?
N19 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
N19 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108 . . ?
C25 C26 C27 120.68(19) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C24 C25 C26 119.4(2) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 N3 0.57(17) . . . . ?
C6 N1 N2 N3 174.31(13) . . . . ?
N1 N2 N3 N4 -0.58(17) . . . . ?
C5 N4 N3 N2 0.36(17) . . . . ?
C38 C33 C34 C35 -0.5(2) . . . . ?
C28 C33 C34 C35 -179.77(13) . . . . ?
C20 N19 C17 O18 10.6(2) . . . . ?
C20 N19 C17 C6 -169.71(14) . . . . ?
C30 N29 C28 C5 -172.65(12) . . . . ?
C30 N29 C28 C33 60.53(17) . . . . ?
C34 C33 C28 N29 -132.93(14) . . . . ?
C38 C33 C28 N29 47.83(19) . . . . ?
C34 C33 C28 C5 103.64(15) . . . . ?
C38 C33 C28 C5 -75.60(17) . . . . ?
N3 N4 C5 N1 0.01(16) . . . . ?
N3 N4 C5 C28 176.37(14) . . . . ?
N2 N1 C5 N4 -0.37(17) . . . . ?
C6 N1 C5 N4 -173.33(14) . . . . ?
N2 N1 C5 C28 -176.90(13) . . . . ?
C6 N1 C5 C28 10.1(2) . . . . ?
N29 C28 C5 N4 -110.16(16) . . . . ?
C33 C28 C5 N4 19.3(2) . . . . ?
N29 C28 C5 N1 65.69(17) . . . . ?
C33 C28 C5 N1 -164.84(13) . . . . ?
C9 C8 C16 C15 -179.21(17) . . . . ?
C7 C8 C16 C15 -5.2(3) . . . . ?
C9 C8 C16 C11 -0.11(17) . . . . ?
C7 C8 C16 C11 173.90(14) . . . . ?
C5 N1 C6 C7 111.46(16) . . . . ?
N2 N1 C6 C7 -60.81(17) . . . . ?
C5 N1 C6 C17 -122.16(16) . . . . ?
N2 N1 C6 C17 65.57(17) . . . . ?
O18 C17 C6 N1 -119.89(14) . . . . ?
N19 C17 C6 N1 60.39(16) . . . . ?
O18 C17 C6 C7 3.29(19) . . . . ?
N19 C17 C6 C7 -176.43(12) . . . . ?
C16 C8 C9 N10 -0.86(18) . . . . ?
C7 C8 C9 N10 -174.83(14) . . . . ?
C11 N10 C9 C8 1.54(19) . . . . ?
C9 C8 C7 C6 102.56(18) . . . . ?
C16 C8 C7 C6 -70.20(19) . . . . ?
N1 C6 C7 C8 -54.60(15) . . . . ?
C17 C6 C7 C8 -177.99(12) . . . . ?
C37 C36 C35 C34 0.6(2) . . . . ?
Cl36 C36 C35 C34 179.49(12) . . . . ?
C33 C34 C35 C36 -0.2(2) . . . . ?
C34 C33 C38 C37 0.8(2) . . . . ?
C28 C33 C38 C37 -179.97(14) . . . . ?
C11 C12 C13 C14 -1.2(2) . . . . ?
C15 C14 C13 C12 0.7(3) . . . . ?
C13 C14 C15 C16 1.0(2) . . . . ?
C11 C16 C15 C14 -2.3(2) . . . . ?
C8 C16 C15 C14 176.77(16) . . . . ?
C9 N10 C11 C12 176.71(16) . . . . ?
C9 N10 C11 C16 -1.55(17) . . . . ?
C13 C12 C11 N10 -178.16(16) . . . . ?
C13 C12 C11 C16 -0.1(2) . . . . ?
C15 C16 C11 N10 -179.72(14) . . . . ?
C8 C16 C11 N10 1.01(16) . . . . ?
C15 C16 C11 C12 1.9(2) . . . . ?
C8 C16 C11 C12 -177.40(14) . . . . ?
C35 C36 C37 C38 -0.3(2) . . . . ?
Cl36 C36 C37 C38 -179.23(12) . . . . ?
C33 C38 C37 C36 -0.4(2) . . . . ?
C28 N29 C30 C31 65.75(17) . . . . ?
C28 N29 C30 C32 -172.71(13) . . . . ?
C24 C23 C22 C27 0.8(3) . . . . ?
C24 C23 C22 C21 179.79(16) . . . . ?
C23 C22 C27 C26 -0.7(3) . . . . ?
C21 C22 C27 C26 -179.62(17) . . . . ?
C23 C22 C21 C20 -107.4(2) . . . . ?
C27 C22 C21 C20 71.6(2) . . . . ?
C22 C23 C24 C25 -0.4(3) . . . . ?
C17 N19 C20 C21 105.94(19) . . . . ?
C22 C21 C20 N19 54.6(2) . . . . ?
C22 C27 C26 C25 0.1(3) . . . . ?
C23 C24 C25 C26 -0.2(3) . . . . ?
C27 C26 C25 C24 0.4(3) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
