# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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#######################################################################

data_nany
_database_code_depnum_ccdc_archive 'CCDC 1866491'
_audit_update_record             
;
2018-09-07 deposited with the CCDC.
2018-11-09 downloaded from the CCDC.
;
_audit_creation_date             2018-05-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            2c
_chemical_name_systematic        ?
_chemical_formula_moiety         'C39 H44 N2 O'
_chemical_formula_sum            'C39 H44 N2 O'
_chemical_formula_weight         556.76
_chemical_melting_point          ?
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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.525(2)
_cell_length_b                   12.498(7)
_cell_length_c                   13.969(6)
_cell_angle_alpha                69.67(5)
_cell_angle_beta                 86.47(3)
_cell_angle_gamma                73.49(3)
_cell_volume                     1650.4(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    25
_cell_measurement_temperature    297
_cell_measurement_theta_max      26.919
_cell_measurement_theta_min      20.035
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.507
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.27
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6680
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.916
_diffrn_reflns_theta_min         3.377
_diffrn_ambient_temperature      297
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_dtime           1.195
_diffrn_detector_type            'scintillation LiI'
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker-Enraf-Nonius MACH3'
_diffrn_measurement_method       'non-profiled ω/2τ scans'
_diffrn_orient_matrix_type       
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      -0.072504
_diffrn_orient_matrix_UB_12      0.008285
_diffrn_orient_matrix_UB_13      0.048917
_diffrn_orient_matrix_UB_21      0.057823
_diffrn_orient_matrix_UB_22      0.020024
_diffrn_orient_matrix_UB_23      0.041509
_diffrn_orient_matrix_UB_31      -0.035180
_diffrn_orient_matrix_UB_32      0.086229
_diffrn_orient_matrix_UB_33      -0.041510
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_source_target            Cu
_diffrn_source_type              'fine-focus sealed tube'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
4 -1 1
-4 1 -1

_diffrn_standards_decay_%        1
_diffrn_standards_decay_corr_max 1.026
_diffrn_standards_decay_corr_min 0.956
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4075
_reflns_number_total             6348
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0084(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         6348
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0604
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0998P)²+0.5316P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1600
_refine_ls_wR_factor_ref         0.1951
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C34(H34), C25(H25), C22(H22), C37(H37)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C15(H15), C9(H9), C18(H18), C11(H11), C6(H6), C8(H8), C7(H7),
 C14(H14), C32(H32), C13(H13), C12(H12), C20(H20), C30(H30), C19(H19), C31(H31)
2.c Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C23(H23A,H23B,H23C), C27(H27A,H27B,H27C), C35(H35A,H35B,
 H35C), C24(H24A,H24B,H24C), C39(H39A,H39B,H39C), C26(H26A,H26B,H26C), C38(H38A,
 H38B,H38C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
N1 N 0.19913(19) 0.88026(17) 0.25985(14) 0.0455(5) Uani 1 1 d . . . . .
N2 N 0.25311(19) 1.11816(16) 0.18354(14) 0.0439(5) Uani 1 1 d . . . . .
C2 C 0.2349(2) 0.9966(2) 0.09553(17) 0.0448(5) Uani 1 1 d . . . . .
C4 C 0.4037(2) 0.7968(2) 0.18008(17) 0.0436(5) Uani 1 1 d . . . . .
C3 C 0.1844(2) 1.1124(2) 0.11500(17) 0.0416(5) Uani 1 1 d . . . . .
C1 C 0.2794(2) 0.8850(2) 0.18758(17) 0.0422(5) Uani 1 1 d . . . . .
C17 C 0.1253(2) 0.7165(2) 0.37300(18) 0.0486(6) Uani 1 1 d . . . . .
C16 C 0.2196(2) 0.7803(2) 0.35230(17) 0.0451(5) Uani 1 1 d . . . . .
C28 C 0.2338(2) 1.2155(2) 0.21842(17) 0.0443(5) Uani 1 1 d . . . . .
C21 C 0.3234(3) 0.7542(2) 0.42153(19) 0.0542(6) Uani 1 1 d . . . . .
C10 C 0.0710(2) 1.2034(2) 0.04934(17) 0.0437(5) Uani 1 1 d . . . . .
C5 C 0.5103(3) 0.8371(2) 0.13609(19) 0.0526(6) Uani 1 1 d . . . . .
H5 H 0.5006 0.9184 0.1090 0.063 Uiso 1 1 calc R . . . .
C15 C 0.0703(3) 1.3213(2) 0.00375(18) 0.0526(6) Uani 1 1 d . . . . .
H15 H 0.1423 1.3457 0.0142 0.063 Uiso 1 1 calc R . . . .
C9 C 0.4193(3) 0.6752(2) 0.21704(19) 0.0510(6) Uani 1 1 d . . . . .
H9 H 0.3484 0.6461 0.2456 0.061 Uiso 1 1 calc R . . . .
C33 C 0.3398(3) 1.2644(2) 0.20818(19) 0.0523(6) Uani 1 1 d . . . . .
C29 C 0.1235(3) 1.2473(2) 0.27434(18) 0.0521(6) Uani 1 1 d . . . . .
C18 C 0.1458(3) 0.6180(3) 0.4612(2) 0.0633(7) Uani 1 1 d . . . . .
H18 H 0.0871 0.5716 0.4754 0.076 Uiso 1 1 calc R . . . .
C34 C 0.0053(3) 1.1978(3) 0.2865(2) 0.0614(7) Uani 1 1 d . . . . .
H34 H 0.0221 1.1412 0.2500 0.074 Uiso 1 1 calc R . . . .
C11 C -0.0368(3) 1.1693(2) 0.0319(2) 0.0561(6) Uani 1 1 d . . . . .
H11 H -0.0360 1.0899 0.0603 0.067 Uiso 1 1 calc R . . . .
C6 C 0.6307(3) 0.7587(3) 0.1317(2) 0.0622(7) Uani 1 1 d . . . . .
H6 H 0.7020 0.7871 0.1032 0.075 Uiso 1 1 calc R . . . .
C8 C 0.5401(3) 0.5975(2) 0.2114(2) 0.0606(7) Uani 1 1 d . . . . .
H8 H 0.5501 0.5161 0.2363 0.073 Uiso 1 1 calc R . . . .
C7 C 0.6454(3) 0.6390(3) 0.1694(2) 0.0653(7) Uani 1 1 d . . . . .
H7 H 0.7267 0.5860 0.1666 0.078 Uiso 1 1 calc R . . . .
C25 C 0.4156(3) 0.8314(3) 0.4067(2) 0.0653(8) Uani 1 1 d . . . . .
H25 H 0.4001 0.8878 0.3364 0.078 Uiso 1 1 calc R . . . .
C14 C -0.0379(3) 1.4028(2) -0.0575(2) 0.0680(8) Uani 1 1 d . . . . .
H14 H -0.0379 1.4817 -0.0893 0.082 Uiso 1 1 calc R . . . .
C32 C 0.3348(3) 1.3442(3) 0.2577(2) 0.0660(8) Uani 1 1 d . . . . .
H32 H 0.4041 1.3783 0.2517 0.079 Uiso 1 1 calc R . . . .
C13 C -0.1448(3) 1.3667(3) -0.0712(2) 0.0715(8) Uani 1 1 d . . . . .
H13 H -0.2181 1.4219 -0.1111 0.086 Uiso 1 1 calc R . . . .
C22 C 0.0061(3) 0.7560(3) 0.3009(2) 0.0622(7) Uani 1 1 d . . . . .
H22 H 0.0378 0.7797 0.2313 0.075 Uiso 1 1 calc R . . . .
C12 C -0.1446(3) 1.2507(3) -0.0266(2) 0.0680(8) Uani 1 1 d . . . . .
H12 H -0.2176 1.2269 -0.0360 0.082 Uiso 1 1 calc R . . . .
C37 C 0.4564(3) 1.2303(3) 0.1450(2) 0.0670(8) Uani 1 1 d . . . . .
H37 H 0.4240 1.2024 0.0963 0.080 Uiso 1 1 calc R . . . .
C20 C 0.3369(3) 0.6549(3) 0.5094(2) 0.0695(8) Uani 1 1 d . . . . .
H20 H 0.4061 0.6340 0.5565 0.083 Uiso 1 1 calc R . . . .
C30 C 0.1249(3) 1.3276(3) 0.3220(2) 0.0649(7) Uani 1 1 d . . . . .
H30 H 0.0527 1.3505 0.3595 0.078 Uiso 1 1 calc R . . . .
C19 C 0.2506(4) 0.5873(3) 0.5280(2) 0.0735(9) Uani 1 1 d . . . . .
H19 H 0.2630 0.5199 0.5864 0.088 Uiso 1 1 calc R . . . .
C31 C 0.2293(3) 1.3740(3) 0.3156(2) 0.0727(8) Uani 1 1 d . . . . .
H31 H 0.2290 1.4256 0.3502 0.087 Uiso 1 1 calc R . . . .
C36 C -0.1224(3) 1.2955(3) 0.2403(3) 0.0866(10) Uani 1 1 d . . . . .
H36A H -0.1423 1.3508 0.2764 0.130 Uiso 1 1 calc GR . . . .
H36B H -0.1940 1.2605 0.2460 0.130 Uiso 1 1 calc GR . . . .
H36C H -0.1109 1.3364 0.1696 0.130 Uiso 1 1 calc GR . . . .
C23 C -0.0600(4) 0.6609(3) 0.3108(3) 0.0981(12) Uani 1 1 d . . . . .
H23A H 0.0051 0.5912 0.3068 0.147 Uiso 1 1 calc GR . . . .
H23B H -0.1260 0.6891 0.2564 0.147 Uiso 1 1 calc GR . . . .
H23C H -0.1014 0.6418 0.3753 0.147 Uiso 1 1 calc GR . . . .
C27 C 0.3814(5) 0.9030(5) 0.4766(4) 0.1296(18) Uani 1 1 d . . . . .
H27A H 0.2934 0.9557 0.4592 0.194 Uiso 1 1 calc GR . . . .
H27B H 0.4434 0.9486 0.4690 0.194 Uiso 1 1 calc GR . . . .
H27C H 0.3857 0.8504 0.5460 0.194 Uiso 1 1 calc GR . . . .
C35 C -0.0128(4) 1.1314(4) 0.3984(3) 0.0964(12) Uani 1 1 d . . . . .
H35A H 0.0650 1.0663 0.4257 0.145 Uiso 1 1 calc GR . . . .
H35B H -0.0885 1.1015 0.4039 0.145 Uiso 1 1 calc GR . . . .
H35C H -0.0264 1.1845 0.4362 0.145 Uiso 1 1 calc GR . . . .
C24 C -0.0936(4) 0.8664(3) 0.3122(4) 0.1033(13) Uani 1 1 d . . . . .
H24A H -0.1295 0.8461 0.3789 0.155 Uiso 1 1 calc GR . . . .
H24B H -0.1641 0.8958 0.2612 0.155 Uiso 1 1 calc GR . . . .
H24C H -0.0499 0.9267 0.3037 0.155 Uiso 1 1 calc GR . . . .
C39 C 0.5071(4) 1.3349(4) 0.0819(3) 0.1036(13) Uani 1 1 d . . . . .
H39A H 0.4339 1.4000 0.0451 0.155 Uiso 1 1 calc GR . . . .
H39B H 0.5692 1.3119 0.0345 0.155 Uiso 1 1 calc GR . . . .
H39C H 0.5501 1.3588 0.1264 0.155 Uiso 1 1 calc GR . . . .
C26 C 0.5606(3) 0.7622(4) 0.4191(3) 0.1089(14) Uani 1 1 d . . . . .
H26A H 0.5802 0.7083 0.4882 0.163 Uiso 1 1 calc GR . . . .
H26B H 0.6142 0.8164 0.4038 0.163 Uiso 1 1 calc GR . . . .
H26C H 0.5796 0.7181 0.3733 0.163 Uiso 1 1 calc GR . . . .
C38 C 0.5657(4) 1.1272(4) 0.2100(4) 0.1136(15) Uani 1 1 d . . . . .
H38A H 0.6033 1.1516 0.2571 0.170 Uiso 1 1 calc GR . . . .
H38B H 0.6334 1.1018 0.1669 0.170 Uiso 1 1 calc GR . . . .
H38C H 0.5300 1.0625 0.2474 0.170 Uiso 1 1 calc GR . . . .
O1 O 0.2405(2) 0.99453(16) 0.00978(13) 0.0638(5) Uani 1 1 d . . . . .


_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
N1 C1 1.272(3) . ?
N1 C16 1.426(3) . ?
N2 C3 1.268(3) . ?
N2 C28 1.420(3) . ?
C2 C3 1.507(3) . ?
C2 C1 1.509(3) . ?
C2 O1 1.205(3) . ?
C4 C1 1.477(3) . ?
C4 C5 1.383(3) . ?
C4 C9 1.387(3) . ?
C3 C10 1.482(3) . ?
C17 C16 1.400(3) . ?
C17 C18 1.381(4) . ?
C17 C22 1.513(4) . ?
C16 C21 1.394(3) . ?
C28 C33 1.395(3) . ?
C28 C29 1.399(3) . ?
C21 C25 1.511(4) . ?
C21 C20 1.389(4) . ?
C10 C15 1.385(3) . ?
C10 C11 1.382(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.386(4) . ?
C9 H9 0.9300 . ?
C9 C8 1.381(4) . ?
C33 C32 1.387(4) . ?
C33 C37 1.516(4) . ?
C29 C34 1.515(4) . ?
C29 C30 1.388(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.368(4) . ?
C34 H34 0.9800 . ?
C34 C36 1.529(4) . ?
C34 C35 1.523(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.368(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.367(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.370(4) . ?
C7 H7 0.9300 . ?
C25 H25 0.9800 . ?
C25 C27 1.504(5) . ?
C25 C26 1.512(5) . ?
C14 H14 0.9300 . ?
C14 C13 1.371(4) . ?
C32 H32 0.9300 . ?
C32 C31 1.374(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.365(4) . ?
C22 H22 0.9800 . ?
C22 C23 1.503(4) . ?
C22 C24 1.530(5) . ?
C12 H12 0.9300 . ?
C37 H37 0.9800 . ?
C37 C39 1.519(5) . ?
C37 C38 1.511(5) . ?
C20 H20 0.9300 . ?
C20 C19 1.364(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.366(4) . ?
C19 H19 0.9300 . ?
C31 H31 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?

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
C1 N1 C16 122.4(2) . . ?
C3 N2 C28 126.8(2) . . ?
C3 C2 C1 117.1(2) . . ?
O1 C2 C3 120.9(2) . . ?
O1 C2 C1 122.0(2) . . ?
C5 C4 C1 118.5(2) . . ?
C5 C4 C9 118.5(2) . . ?
C9 C4 C1 123.0(2) . . ?
N2 C3 C2 112.6(2) . . ?
N2 C3 C10 130.0(2) . . ?
C10 C3 C2 117.30(19) . . ?
N1 C1 C2 113.3(2) . . ?
N1 C1 C4 129.7(2) . . ?
C4 C1 C2 116.9(2) . . ?
C16 C17 C22 120.4(2) . . ?
C18 C17 C16 117.3(2) . . ?
C18 C17 C22 122.3(2) . . ?
C17 C16 N1 116.8(2) . . ?
C21 C16 N1 120.8(2) . . ?
C21 C16 C17 122.2(2) . . ?
C33 C28 N2 116.2(2) . . ?
C33 C28 C29 121.8(2) . . ?
C29 C28 N2 121.2(2) . . ?
C16 C21 C25 122.9(2) . . ?
C20 C21 C16 117.1(3) . . ?
C20 C21 C25 119.9(2) . . ?
C15 C10 C3 122.1(2) . . ?
C11 C10 C3 119.0(2) . . ?
C11 C10 C15 118.9(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C10 C15 H15 120.1 . . ?
C10 C15 C14 119.9(3) . . ?
C14 C15 H15 120.1 . . ?
C4 C9 H9 120.0 . . ?
C8 C9 C4 119.9(2) . . ?
C8 C9 H9 120.0 . . ?
C28 C33 C37 120.6(2) . . ?
C32 C33 C28 117.9(3) . . ?
C32 C33 C37 121.5(2) . . ?
C28 C29 C34 123.8(2) . . ?
C30 C29 C28 117.3(2) . . ?
C30 C29 C34 119.0(3) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 C17 121.3(3) . . ?
C19 C18 H18 119.3 . . ?
C29 C34 H34 108.0 . . ?
C29 C34 C36 111.7(2) . . ?
C29 C34 C35 111.3(3) . . ?
C36 C34 H34 108.0 . . ?
C35 C34 H34 108.0 . . ?
C35 C34 C36 109.8(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.5 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0(3) . . ?
C7 C6 H6 120.0 . . ?
C9 C8 H8 119.7 . . ?
C7 C8 C9 120.7(3) . . ?
C7 C8 H8 119.7 . . ?
C6 C7 C8 119.8(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C21 C25 H25 107.2 . . ?
C21 C25 C26 113.2(3) . . ?
C27 C25 C21 110.2(3) . . ?
C27 C25 H25 107.2 . . ?
C27 C25 C26 111.3(3) . . ?
C26 C25 H25 107.2 . . ?
C15 C14 H14 120.1 . . ?
C13 C14 C15 119.8(3) . . ?
C13 C14 H14 120.1 . . ?
C33 C32 H32 119.4 . . ?
C31 C32 C33 121.3(3) . . ?
C31 C32 H32 119.4 . . ?
C14 C13 H13 119.7 . . ?
C12 C13 C14 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C17 C22 H22 107.0 . . ?
C17 C22 C24 110.1(3) . . ?
C23 C22 C17 114.5(3) . . ?
C23 C22 H22 107.0 . . ?
C23 C22 C24 110.9(3) . . ?
C24 C22 H22 107.0 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.1 . . ?
C33 C37 H37 106.6 . . ?
C33 C37 C39 113.0(3) . . ?
C39 C37 H37 106.6 . . ?
C38 C37 C33 111.4(3) . . ?
C38 C37 H37 106.6 . . ?
C38 C37 C39 112.1(3) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 C21 121.4(3) . . ?
C19 C20 H20 119.3 . . ?
C29 C30 H30 119.0 . . ?
C31 C30 C29 122.0(3) . . ?
C31 C30 H30 119.0 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C32 C31 H31 120.1 . . ?
C30 C31 C32 119.7(3) . . ?
C30 C31 H31 120.1 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C37 C39 H39A 109.5 . . ?
C37 C39 H39B 109.5 . . ?
C37 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_nany_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1866492'
_audit_update_record             
;
2018-09-07 deposited with the CCDC.
2018-11-09 downloaded from the CCDC.
;
_audit_creation_date             2018-05-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            5
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9.5 H11 Cl0.5 N, B0.5 F2'
_chemical_formula_sum            'C9.50 H11 B0.50 Cl0.50 F2 N'
_chemical_formula_weight         200.32
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/2, x+1/2, z+3/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+1/4'
'x+1/2, -y+1/2, -z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   9.9401(14)
_cell_length_b                   9.9401(14)
_cell_length_c                   19.673(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1943.8(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12451
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.500
_cell_measurement_theta_min      2.913
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.602446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.0822 before and 0.0395 after correction.
The Ratio of minimum to maximum transmission is 0.6024.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12451
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         2.913
_diffrn_ambient_temperature      200.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            KappaCCD
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '2 circles diffractometer'
_diffrn_measurement_device_type  'Bruker-AXS-enraf-nonius KappaCCD'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_collimation    'Montel optic'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec ISG250'
_diffrn_source_target            Mo
_diffrn_source_type              'Microfocus sealed tube'
_reflns_Friedel_coverage         0.640
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                1948
_reflns_number_total             2224
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    ?
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 728 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         2224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0412P)²+0.6158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0938
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C10(H10), C9(H9), C8(H8)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Cl1 Cl 0.25762(5) 0.74238(5) 0.7500 0.0374(2) Uani 1 2 d S T P . .
F2 F 0.45766(19) 0.2976(2) 0.49993(14) 0.0833(7) Uani 1 1 d . . . . .
N1 N 0.5133(2) 0.49491(19) 0.66824(9) 0.0330(4) Uani 1 1 d . . . . .
C2 C 0.3828(2) 0.6172(2) 0.7500 0.0296(6) Uani 1 2 d S T P . .
F1 F 0.2647(3) 0.2668(2) 0.44341(13) 0.1000(8) Uani 1 1 d . . . . .
C1 C 0.4597(2) 0.6094(2) 0.68989(11) 0.0293(5) Uani 1 1 d . . . . .
C5 C 0.4740(2) 0.7311(2) 0.64642(11) 0.0312(5) Uani 1 1 d . . . . .
C4 C 0.4672(3) 0.3630(2) 0.69159(14) 0.0419(6) Uani 1 1 d . . . . .
H4A H 0.5230 0.3334 0.7298 0.063 Uiso 1 1 calc GR . . . .
H4B H 0.4745 0.2980 0.6543 0.063 Uiso 1 1 calc GR . . . .
H4C H 0.3732 0.3694 0.7062 0.063 Uiso 1 1 calc GR . . . .
C3 C 0.6175(3) 0.4906(3) 0.61473(13) 0.0401(6) Uani 1 1 d . . . . .
H3A H 0.5765 0.4631 0.5716 0.060 Uiso 1 1 calc GR . . . .
H3B H 0.6874 0.4258 0.6275 0.060 Uiso 1 1 calc GR . . . .
H3C H 0.6577 0.5800 0.6096 0.060 Uiso 1 1 calc GR . . . .
B1 B 0.3221(3) 0.3221(3) 0.5000 0.0463(10) Uani 1 2 d S T P . .
C7 C 0.5414(3) 0.9611(3) 0.63199(15) 0.0495(7) Uani 1 1 d . . . . .
H7 H 0.5869 1.0386 0.6484 0.059 Uiso 1 1 calc R . . . .
C6 C 0.5380(3) 0.8445(2) 0.67062(13) 0.0399(6) Uani 1 1 d . . . . .
H6 H 0.5799 0.8427 0.7140 0.048 Uiso 1 1 calc R . . . .
C10 C 0.4152(2) 0.7320(3) 0.58216(12) 0.0379(5) Uani 1 1 d . . . . .
H10 H 0.3742 0.6531 0.5645 0.045 Uiso 1 1 calc R . . . .
C9 C 0.4172(3) 0.8497(3) 0.54420(14) 0.0484(7) Uani 1 1 d . . . . .
H9 H 0.3764 0.8517 0.5006 0.058 Uiso 1 1 calc R . . . .
C8 C 0.4781(3) 0.9636(3) 0.56948(15) 0.0524(8) Uani 1 1 d . . . . .
H8 H 0.4766 1.0445 0.5438 0.063 Uiso 1 1 calc R . . . .


_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
Cl1 C2 1.760(3) . ?
F2 B1 1.369(3) . ?
N1 C1 1.326(3) . ?
N1 C4 1.463(3) . ?
N1 C3 1.478(3) . ?
C2 C1 1.410(3) . ?
C2 C1 1.410(3) 8_666 ?
F1 B1 1.367(3) . ?
C1 C5 1.489(3) . ?
C5 C6 1.379(3) . ?
C5 C10 1.393(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
B1 F2 1.369(3) 7_556 ?
B1 F1 1.367(3) 7_556 ?
C7 H7 0.9500 . ?
C7 C6 1.386(4) . ?
C7 C8 1.382(4) . ?
C6 H6 0.9500 . ?
C10 H10 0.9500 . ?
C10 C9 1.388(4) . ?
C9 H9 0.9500 . ?
C9 C8 1.376(5) . ?
C8 H8 0.9500 . ?

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
C1 N1 C4 122.85(19) . . ?
C1 N1 C3 122.3(2) . . ?
C4 N1 C3 114.66(19) . . ?
C1 C2 Cl1 114.97(14) 8_666 . ?
C1 C2 Cl1 114.97(14) . . ?
C1 C2 C1 130.1(3) . 8_666 ?
N1 C1 C2 122.3(2) . . ?
N1 C1 C5 118.34(19) . . ?
C2 C1 C5 119.3(2) . . ?
C6 C5 C1 120.7(2) . . ?
C6 C5 C10 120.1(2) . . ?
C10 C5 C1 119.1(2) . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
F2 B1 F2 110.5(3) 7_556 . ?
F1 B1 F2 108.80(16) 7_556 . ?
F1 B1 F2 109.80(16) 7_556 7_556 ?
F1 B1 F2 109.80(16) . . ?
F1 B1 F2 108.79(16) . 7_556 ?
F1 B1 F1 109.1(4) 7_556 . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C8 C7 C6 119.5(3) . . ?
C5 C6 C7 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C5 C10 H10 120.4 . . ?
C9 C10 C5 119.2(3) . . ?
C9 C10 H10 120.4 . . ?
C10 C9 H9 119.8 . . ?
C8 C9 C10 120.3(3) . . ?
C8 C9 H9 119.8 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8 119.8 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_nany_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1866493'
_audit_update_record             
;
2018-09-07 deposited with the CCDC.
2018-11-09 downloaded from the CCDC.
;
_audit_creation_date             2018-05-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            7H+
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H23 N2 O, B F4, 2.2(C0.23 H0.45 Cl0.45)'
_chemical_formula_sum            'C19.50 H24 B Cl F4 N2 O'
_chemical_formula_weight         424.67
_chemical_melting_point          ?
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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   9.1627(18)
_cell_length_b                   8.6433(17)
_cell_length_c                   26.423(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.17(3)
_cell_angle_gamma                90
_cell_volume                     2092.2(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    20252
_cell_measurement_temperature    200
_cell_measurement_theta_max      25.000
_cell_measurement_theta_min      1.542
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.313663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2004/1 (Bruker,2004) was used for absorption correction. R(int) was 0.1483 before and 0.0991 after correction. The Ratio of minimum to maximum transmission is 0.3137. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            20252
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.542
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            KappaCCD
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '4 circles diffractometer'
_diffrn_measurement_device_type  Incoatec-Bruker-AXS-enraf-noniusKappaCCD
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_collimation    ?
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec ISG250'
_diffrn_source_target            Mo
_diffrn_source_type              'Microfocus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2838
_reflns_number_total             3651
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    ?
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         3651
_refine_ls_number_restraints     139
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0670
_refine_ls_restrained_S_all      1.177
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0715P)²+1.9494P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1712
_refine_ls_wR_factor_ref         0.1887
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C20B-Cl1B
 1.7 with sigma of 0.02
 C20B-Cl1B_$1
 1.7 with sigma of 0.02
 C20A-Cl1A
 1.7 with sigma of 0.02
 C20A-Cl1A_$1
 1.7 with sigma of 0.02
 O1B-C2
 1.4 with sigma of 0.02
3. Rigid bond restraints
 C20B, Cl1B, C20A, Cl1A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F2A, F2B, F3A, F3B, F4, F1A, F1B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C2, O1B, O1A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C20B \\sim Cl1B \\sim C20A \\sim Cl1A: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
F2A \\sim F2B \\sim F3A \\sim F3B \\sim F1A \\sim F1B \\sim F4 \\sim B1: within
1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
O1B \\sim O1A \\sim C2: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
Uanis(O1B) = Uanis(O1A)
5. Others
 Sof(Cl1B)=1-FVAR(1)
 Sof(C20B)=Sof(H20B)=Sof(H20A)=0.5*(1-FVAR(2))
 Sof(C20A)=Sof(H20D)=Sof(H20C)=0.5*FVAR(2)
 Sof(Cl1A)=FVAR(1)
 Sof(F2B)=Sof(F3B)=Sof(F1B)=1-FVAR(2)
 Sof(F2A)=Sof(F3A)=Sof(F1A)=FVAR(2)
 Sof(O1B)=Sof(H1B)=1-FVAR(3)
 Sof(O1A)=Sof(H1A)=FVAR(3)
6.a Secondary CH2 refined with riding coordinates:
 C20B(H20B,H20A), C20A(H20D,H20C)
6.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C19(H19), C15(H15), C13(H13), C12(H12), C18(H18), C16(H16), C11(H11),
 C10(H10), C17(H17)
6.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C6(H6A,H6B,H6C), C5(H5A,H5B,H5C), C4(H4A,H4B,H4C)
6.d Idealised tetrahedral OH refined as rotating group:
 O1B(H1B), O1A(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O1B O -0.1157(16) 0.742(3) 0.5874(5) 0.049(2) Uani 0.62(7) 1 d D U P A 2
H1B H -0.1314 0.8316 0.5958 0.073 Uiso 0.62(7) 1 calc GR . P A 2
F4 F 0.9825(2) 0.0632(3) 0.64025(10) 0.0880(7) Uani 1 1 d . U . . .
N2 N -0.0592(2) 0.7001(3) 0.69212(8) 0.0432(6) Uani 1 1 d . . . . .
F2B F 0.839(3) 0.255(3) 0.6654(16) 0.126(10) Uani 0.153(10) 1 d . U P B 2
F3B F 0.753(4) 0.053(4) 0.6763(13) 0.106(11) Uani 0.153(10) 1 d . U P B 2
N1 N 0.1260(3) 0.6751(3) 0.52426(9) 0.0554(7) Uani 1 1 d . . . . .
F1B F 0.741(2) 0.122(5) 0.6062(7) 0.135(12) Uani 0.153(10) 1 d . U P B 2
C8 C 0.2453(3) 0.5352(3) 0.59245(9) 0.0409(6) Uani 1 1 d . . . . .
C14 C 0.1970(3) 0.7461(3) 0.67966(10) 0.0400(6) Uani 1 1 d . . . . .
C3 C 0.0496(3) 0.7087(3) 0.65950(9) 0.0377(6) Uani 1 1 d . . . . .
C2 C 0.0239(3) 0.6945(3) 0.60688(10) 0.0425(6) Uani 1 1 d D U . . .
C9 C 0.2079(3) 0.4028(3) 0.61888(10) 0.0472(7) Uani 1 1 d . . . . .
H9 H 0.1102 0.3802 0.6243 0.057 Uiso 1 1 calc R . . . .
C19 C 0.2776(3) 0.8627(3) 0.65806(11) 0.0468(7) Uani 1 1 d . . . . .
H19 H 0.2387 0.9188 0.6309 0.056 Uiso 1 1 calc R . . . .
C15 C 0.2571(3) 0.6633(4) 0.72046(11) 0.0500(7) Uani 1 1 d . . . . .
H15 H 0.2047 0.5831 0.7349 0.060 Uiso 1 1 calc R . . . .
C1 C 0.1300(3) 0.6412(3) 0.57368(10) 0.0438(6) Uani 1 1 d . . . . .
C7 C -0.0549(3) 0.7736(4) 0.74184(11) 0.0544(8) Uani 1 1 d . . . . .
H7A H -0.0517 0.6954 0.7676 0.082 Uiso 1 1 calc GR . . . .
H7B H -0.1405 0.8361 0.7457 0.082 Uiso 1 1 calc GR . . . .
H7C H 0.0305 0.8376 0.7449 0.082 Uiso 1 1 calc GR . . . .
C13 C 0.3917(3) 0.5673(4) 0.58478(11) 0.0520(7) Uani 1 1 d . . . . .
H13 H 0.4178 0.6554 0.5669 0.062 Uiso 1 1 calc R . . . .
C12 C 0.4979(3) 0.4701(5) 0.60340(12) 0.0615(9) Uani 1 1 d . . . . .
H12 H 0.5958 0.4928 0.5985 0.074 Uiso 1 1 calc R . . . .
B1 B 0.8402(4) 0.1069(4) 0.64282(13) 0.0477(8) Uani 1 1 d . . . . .
C18 C 0.4163(3) 0.8963(4) 0.67671(14) 0.0593(9) Uani 1 1 d . . . . .
H18 H 0.4715 0.9731 0.6616 0.071 Uiso 1 1 calc R . . . .
C16 C 0.3926(3) 0.7002(4) 0.73911(13) 0.0607(9) Uani 1 1 d . . . . .
H16 H 0.4312 0.6460 0.7667 0.073 Uiso 1 1 calc R . . . .
C6 C -0.1950(3) 0.6190(4) 0.68058(13) 0.0600(8) Uani 1 1 d . . . . .
H6A H -0.2659 0.6910 0.6673 0.090 Uiso 1 1 calc GR . . . .
H6B H -0.2310 0.5727 0.7109 0.090 Uiso 1 1 calc GR . . . .
H6C H -0.1778 0.5400 0.6559 0.090 Uiso 1 1 calc GR . . . .
C11 C 0.4589(4) 0.3379(5) 0.62950(12) 0.0669(10) Uani 1 1 d . . . . .
H11 H 0.5308 0.2714 0.6420 0.080 Uiso 1 1 calc R . . . .
C10 C 0.3149(4) 0.3050(4) 0.63698(12) 0.0611(9) Uani 1 1 d . . . . .
H10 H 0.2894 0.2159 0.6544 0.073 Uiso 1 1 calc R . . . .
C17 C 0.4724(3) 0.8156(4) 0.71777(15) 0.0643(10) Uani 1 1 d . . . . .
H17 H 0.5645 0.8399 0.7309 0.077 Uiso 1 1 calc R . . . .
C5 C 0.1985(4) 0.5816(4) 0.48622(12) 0.0696(10) Uani 1 1 d . . . . .
H5A H 0.2845 0.6343 0.4752 0.104 Uiso 1 1 calc GR . . . .
H5B H 0.1333 0.5656 0.4578 0.104 Uiso 1 1 calc GR . . . .
H5C H 0.2254 0.4834 0.5006 0.104 Uiso 1 1 calc GR . . . .
C4 C 0.0507(5) 0.8111(5) 0.50379(14) 0.0782(11) Uani 1 1 d . . . . .
H4A H -0.0450 0.7821 0.4918 0.117 Uiso 1 1 calc GR . . . .
H4B H 0.1052 0.8528 0.4763 0.117 Uiso 1 1 calc GR . . . .
H4C H 0.0425 0.8878 0.5299 0.117 Uiso 1 1 calc GR . . . .
Cl1B Cl 0.6223(10) 0.958(2) 0.4755(4) 0.212(4) Uani 0.454(13) 1 d D U P C 2
C20B C 0.456(3) 0.906(2) 0.4894(8) 0.182(10) Uani 0.227(6) 1 d D U P C 2
H20B H 0.4586 0.8092 0.5078 0.219 Uiso 0.227(6) 1 calc R . P C 2
H20A H 0.3992 0.8908 0.4584 0.219 Uiso 0.227(6) 1 calc R . P C 2
C20A C 0.482(2) 0.985(2) 0.4708(6) 0.124(6) Uani 0.273(6) 1 d D U P C 1
H20D H 0.4043 0.9214 0.4567 0.149 Uiso 0.273(6) 1 calc R . P C 1
H20C H 0.5312 1.0307 0.4422 0.149 Uiso 0.273(6) 1 calc R . P C 1
Cl1A Cl 0.6045(5) 0.8599(7) 0.4979(2) 0.137(2) Uani 0.546(13) 1 d D U P C 1
F2A F 0.8226(4) 0.2524(4) 0.6253(2) 0.0945(15) Uani 0.847(10) 1 d . U P B 1
F3A F 0.7968(8) 0.0953(10) 0.69085(19) 0.116(2) Uani 0.847(10) 1 d . U P B 1
F1A F 0.7624(4) 0.0039(5) 0.61331(15) 0.1033(15) Uani 0.847(10) 1 d . U P B 1
O1A O -0.118(3) 0.708(3) 0.5834(6) 0.049(2) Uani 0.38(7) 1 d . U P A 1
H1A H -0.1570 0.7887 0.5928 0.073 Uiso 0.38(7) 1 calc GR . P A 1


_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
O1B H1B 0.8200 . ?
O1B C2 1.429(15) . ?
F4 B1 1.361(4) . ?
N2 C3 1.333(3) . ?
N2 C7 1.459(4) . ?
N2 C6 1.455(4) . ?
F2B B1 1.41(2) . ?
F3B B1 1.29(3) . ?
N1 C1 1.338(4) . ?
N1 C5 1.460(4) . ?
N1 C4 1.461(4) . ?
F1B B1 1.322(16) . ?
C8 C9 1.387(4) . ?
C8 C1 1.477(4) . ?
C8 C13 1.388(4) . ?
C14 C3 1.478(4) . ?
C14 C19 1.380(4) . ?
C14 C15 1.397(4) . ?
C3 C2 1.411(4) . ?
C2 C1 1.401(4) . ?
C2 O1A 1.44(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.373(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.384(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.364(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C12 1.369(5) . ?
C12 H12 0.9300 . ?
C12 C11 1.385(5) . ?
B1 F2A 1.348(5) . ?
B1 F3A 1.341(6) . ?
B1 F1A 1.373(4) . ?
C18 H18 0.9300 . ?
C18 C17 1.380(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.365(5) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C11 H11 0.9300 . ?
C11 C10 1.368(5) . ?
C10 H10 0.9300 . ?
C17 H17 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
Cl1B C20B 1.671(18) 3_676 ?
Cl1B C20B 1.634(18) . ?
C20B Cl1B 1.671(18) 3_676 ?
C20B H20B 0.9700 . ?
C20B H20A 0.9700 . ?
C20A H20D 0.9700 . ?
C20A H20C 0.9700 . ?
C20A Cl1A 1.771(15) 3_676 ?
C20A Cl1A 1.704(16) . ?
Cl1A C20A 1.771(15) 3_676 ?
O1A H1A 0.8200 . ?

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
C2 O1B H1B 109.5 . . ?
C3 N2 C7 123.4(2) . . ?
C3 N2 C6 122.6(2) . . ?
C6 N2 C7 114.0(2) . . ?
C1 N1 C5 123.1(3) . . ?
C1 N1 C4 122.7(3) . . ?
C5 N1 C4 114.1(3) . . ?
C9 C8 C1 119.9(3) . . ?
C9 C8 C13 119.2(3) . . ?
C13 C8 C1 120.9(3) . . ?
C19 C14 C3 120.2(2) . . ?
C19 C14 C15 119.2(3) . . ?
C15 C14 C3 120.6(3) . . ?
N2 C3 C14 118.0(2) . . ?
N2 C3 C2 121.4(2) . . ?
C2 C3 C14 120.5(2) . . ?
C3 C2 O1B 117.4(7) . . ?
C3 C2 O1A 123.3(7) . . ?
C1 C2 O1B 119.8(7) . . ?
C1 C2 C3 122.8(2) . . ?
C1 C2 O1A 113.1(7) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C14 C19 H19 120.0 . . ?
C14 C19 C18 120.1(3) . . ?
C18 C19 H19 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
N1 C1 C8 118.0(2) . . ?
N1 C1 C2 122.2(3) . . ?
C2 C1 C8 119.7(2) . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8 C13 H13 119.8 . . ?
C12 C13 C8 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C13 C12 H12 120.1 . . ?
C13 C12 C11 119.8(3) . . ?
C11 C12 H12 120.1 . . ?
F4 B1 F2B 106.6(11) . . ?
F4 B1 F1A 106.2(3) . . ?
F3B B1 F4 122.9(19) . . ?
F3B B1 F2B 92(2) . . ?
F3B B1 F1B 96(2) . . ?
F1B B1 F4 129.6(10) . . ?
F1B B1 F2B 102.1(17) . . ?
F2A B1 F4 110.5(3) . . ?
F2A B1 F1A 110.6(3) . . ?
F3A B1 F4 109.2(4) . . ?
F3A B1 F2A 111.1(5) . . ?
F3A B1 F1A 109.2(4) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 C19 119.9(3) . . ?
C17 C18 H18 120.1 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.8(3) . . ?
C17 C16 H16 119.6 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C11 H11 119.9 . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11 119.9 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 C18 120.0(3) . . ?
C16 C17 H17 120.0 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C20B Cl1B C20B 69.7(14) . 3_676 ?
Cl1B C20B Cl1B 110.3(14) . 3_676 ?
Cl1B C20B H20B 109.6 3_676 . ?
Cl1B C20B H20B 109.6 . . ?
Cl1B C20B H20A 109.6 . . ?
Cl1B C20B H20A 109.6 3_676 . ?
H20B C20B H20A 108.1 . . ?
H20D C20A H20C 106.3 . . ?
Cl1A C20A H20D 105.9 3_676 . ?
Cl1A C20A H20D 105.9 . . ?
Cl1A C20A H20C 105.9 . . ?
Cl1A C20A H20C 105.9 3_676 . ?
Cl1A C20A Cl1A 125.6(10) . 3_676 ?
C20A Cl1A C20A 54.4(10) . 3_676 ?
C2 O1A H1A 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_nany_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1866494'
_audit_update_record             
;
2018-09-07 deposited with the CCDC.
2018-11-09 downloaded from the CCDC.
;
_audit_creation_date             2018-05-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            2d
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H22 N4 O'
_chemical_formula_sum            'C19 H22 N4 O'
_chemical_formula_weight         322.40
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   12.168(2)
_cell_length_b                   21.152(4)
_cell_length_c                   6.9588(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1790.9(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15859
_cell_measurement_temperature    200
_cell_measurement_theta_max      30.000
_cell_measurement_theta_min      1.926
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.718632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.2649 before and 0.0302 after correction.
The Ratio of minimum to maximum transmission is 0.7186.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.32
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            15859
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         1.926
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            KappaCCD
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '4 circles diffractometer'
_diffrn_measurement_device_type  'Bruker-AXS-enraf-nonius KappaCCD'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_collimation    'Montel optic'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec ISG250'
_diffrn_source_target            Mo
_diffrn_source_type              'Microfocus sealed tube'
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.883
_reflns_number_gt                4194
_reflns_number_total             4928
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    ?
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1623 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4928
_refine_ls_number_restraints     193
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0609P)²+0.2524P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1241
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C14A-N4
 1.4 with sigma of 0.02
 N4-C14B
 1.4 with sigma of 0.02
 C14A-C15A
 1.4 with sigma of 0.02
 C15B-C14B
 1.4 with sigma of 0.02
 C14A-C19A
 1.4 with sigma of 0.02
 C14B-C19B
 1.4 with sigma of 0.02
3. Rigid bond restraints
 C14B, C15B, C19B, C18B, C17B, C16B, C15A, C16A, C17A, C18A, C19A, C14A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C14B \\sim C15B \\sim C19B \\sim C18B \\sim C17B \\sim C16B \\sim C15A \\sim
C16A \\sim C17A \\sim C18A \\sim C19A \\sim C14A: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
5. Others
 Sof(C14B)=Sof(C15B)=Sof(H15B)=Sof(C19B)=Sof(H19B)=Sof(C18B)=Sof(H18B)=
 Sof(C17B)=Sof(H17B)=Sof(C16B)=Sof(H16B)=1-FVAR(1)
 Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=Sof(C18A)=
 Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C14A)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C9(H9), C11(H11), C12(H12), C15B(H15B), C10(H10), C19B(H19B),
 C18B(H18B), C17B(H17B), C16B(H16B), C15A(H15A), C16A(H16A), C17A(H17A),
 C18A(H18A), C19A(H19A)
6.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C4(H4A,H4B,H4C), C7(H7A,H7B,H7C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O1 O 1.04583(15) 0.40220(8) 0.1778(3) 0.0578(5) Uani 1 1 d . . . . .
N3 N 0.83455(14) 0.41152(8) 0.4734(3) 0.0396(4) Uani 1 1 d . . . . .
C1 C 0.86338(16) 0.39305(8) 0.3051(3) 0.0358(4) Uani 1 1 d . . . . .
N1 N 0.80845(16) 0.38978(9) 0.1373(3) 0.0462(4) Uani 1 1 d . . . . .
C8 C 0.72691(15) 0.42581(9) 0.5343(3) 0.0379(4) Uani 1 1 d . . . . .
C2 C 0.98675(16) 0.38333(9) 0.3039(3) 0.0387(4) Uani 1 1 d . . . . .
N4 N 1.02360(17) 0.29238(11) 0.5069(3) 0.0553(5) Uani 1 1 d D . . . .
C3 C 1.03469(16) 0.35143(11) 0.4799(3) 0.0428(4) Uani 1 1 d . . . . .
C14B C 0.9747(17) 0.2542(15) 0.354(3) 0.047(3) Uani 0.49(2) 1 d D U P A 2
C13 C 0.70408(19) 0.48590(10) 0.6063(3) 0.0457(5) Uani 1 1 d . . . . .
H13 H 0.7594 0.5176 0.6057 0.055 Uiso 1 1 calc R . . . .
N2 N 1.0965(2) 0.38812(13) 0.5970(4) 0.0732(8) Uani 1 1 d . . . . .
C9 C 0.64610(17) 0.37938(11) 0.5429(4) 0.0443(4) Uani 1 1 d . . . . .
H9 H 0.6615 0.3378 0.4990 0.053 Uiso 1 1 calc R . . . .
C11 C 0.5205(2) 0.45331(14) 0.6836(4) 0.0562(6) Uani 1 1 d . . . . .
H11 H 0.4498 0.4627 0.7339 0.067 Uiso 1 1 calc R . . . .
C12 C 0.6007(2) 0.49929(12) 0.6785(4) 0.0540(5) Uani 1 1 d . . . . .
H12 H 0.5849 0.5405 0.7251 0.065 Uiso 1 1 calc R . . . .
C5 C 0.69989(19) 0.41756(13) 0.1117(4) 0.0549(6) Uani 1 1 d . . . . .
H5A H 0.6437 0.3874 0.1536 0.082 Uiso 1 1 calc GR . . . .
H5B H 0.6887 0.4278 -0.0243 0.082 Uiso 1 1 calc GR . . . .
H5C H 0.6943 0.4563 0.1885 0.082 Uiso 1 1 calc GR . . . .
C15B C 0.8668(9) 0.2247(6) 0.365(2) 0.065(3) Uani 0.49(2) 1 d D U P A 2
H15B H 0.8223 0.2314 0.4752 0.078 Uiso 0.49(2) 1 calc R . P A 2
C10 C 0.54338(18) 0.39384(13) 0.6155(4) 0.0529(5) Uani 1 1 d . . . . .
H10 H 0.4879 0.3622 0.6183 0.063 Uiso 1 1 calc R . . . .
C19B C 1.0299(15) 0.2422(9) 0.182(3) 0.053(3) Uani 0.49(2) 1 d D U P A 2
H19B H 1.1006 0.2604 0.1655 0.063 Uiso 0.49(2) 1 calc R . P A 2
C4 C 0.8477(3) 0.35383(16) -0.0279(4) 0.0744(9) Uani 1 1 d . . . . .
H4A H 0.8682 0.3830 -0.1313 0.112 Uiso 1 1 calc GR . . . .
H4B H 0.7894 0.3255 -0.0729 0.112 Uiso 1 1 calc GR . . . .
H4C H 0.9121 0.3288 0.0096 0.112 Uiso 1 1 calc GR . . . .
C7 C 1.1567(3) 0.3579(3) 0.7519(5) 0.1156(19) Uani 1 1 d . . . . .
H7A H 1.1339 0.3136 0.7623 0.173 Uiso 1 1 calc GR . . . .
H7B H 1.1411 0.3798 0.8730 0.173 Uiso 1 1 calc GR . . . .
H7C H 1.2357 0.3600 0.7250 0.173 Uiso 1 1 calc GR . . . .
C18B C 0.9874(9) 0.2044(6) 0.029(3) 0.072(3) Uani 0.49(2) 1 d . U P A 2
H18B H 1.0283 0.1985 -0.0856 0.087 Uiso 0.49(2) 1 calc R . P A 2
C17B C 0.8854(10) 0.1766(6) 0.052(3) 0.088(4) Uani 0.49(2) 1 d . U P A 2
H17B H 0.8559 0.1506 -0.0465 0.105 Uiso 0.49(2) 1 calc R . P A 2
C6 C 1.0944(3) 0.45663(18) 0.5893(7) 0.1016(15) Uani 1 1 d . . . . .
H6A H 1.1647 0.4722 0.5398 0.152 Uiso 1 1 calc GR . . . .
H6B H 1.0821 0.4735 0.7186 0.152 Uiso 1 1 calc GR . . . .
H6C H 1.0348 0.4704 0.5042 0.152 Uiso 1 1 calc GR . . . .
C16B C 0.8279(10) 0.1868(6) 0.216(4) 0.082(5) Uani 0.49(2) 1 d . U P A 2
H16B H 0.7581 0.1672 0.2298 0.099 Uiso 0.49(2) 1 calc R . P A 2
C15A C 0.8648(8) 0.2356(5) 0.4451(17) 0.0528(19) Uani 0.51(2) 1 d D U P A 1
H15A H 0.8354 0.2483 0.5655 0.063 Uiso 0.51(2) 1 calc R . P A 1
C16A C 0.8081(8) 0.1949(6) 0.325(2) 0.069(3) Uani 0.51(2) 1 d . U P A 1
H16A H 0.7361 0.1817 0.3599 0.083 Uiso 0.51(2) 1 calc R . P A 1
C17A C 0.8543(13) 0.1731(5) 0.156(2) 0.068(4) Uani 0.51(2) 1 d . U P A 1
H17A H 0.8151 0.1440 0.0781 0.081 Uiso 0.51(2) 1 calc R . P A 1
C18A C 0.9554(12) 0.1931(5) 0.1018(17) 0.065(3) Uani 0.51(2) 1 d . U P A 1
H18A H 0.9873 0.1784 -0.0146 0.078 Uiso 0.51(2) 1 calc R . P A 1
C19A C 1.0116(16) 0.2351(10) 0.218(3) 0.054(3) Uani 0.51(2) 1 d D U P A 1
H19A H 1.0830 0.2491 0.1826 0.065 Uiso 0.51(2) 1 calc R . P A 1
C14A C 0.9640(18) 0.2567(16) 0.383(3) 0.050(3) Uani 0.51(2) 1 d D U P A 1


_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
O1 C2 1.202(3) . ?
N3 C1 1.283(3) . ?
N3 C8 1.409(3) . ?
C1 N1 1.347(3) . ?
C1 C2 1.515(3) . ?
N1 C5 1.457(3) . ?
N1 C4 1.459(3) . ?
C8 C13 1.394(3) . ?
C8 C9 1.391(3) . ?
C2 C3 1.515(3) . ?
N4 C3 1.270(3) . ?
N4 C14B 1.465(15) . ?
N4 C14A 1.354(16) . ?
C3 N2 1.353(3) . ?
C14B C15B 1.455(15) . ?
C14B C19B 1.394(16) . ?
C13 H13 0.9500 . ?
C13 C12 1.384(3) . ?
N2 C7 1.451(4) . ?
N2 C6 1.450(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.382(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.378(4) . ?
C11 C10 1.373(4) . ?
C12 H12 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C15B H15B 0.9500 . ?
C15B C16B 1.394(19) . ?
C10 H10 0.9500 . ?
C19B H19B 0.9500 . ?
C19B C18B 1.43(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C18B H18B 0.9500 . ?
C18B C17B 1.383(13) . ?
C17B H17B 0.9500 . ?
C17B C16B 1.355(18) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C16B H16B 0.9500 . ?
C15A H15A 0.9500 . ?
C15A C16A 1.382(12) . ?
C15A C14A 1.357(17) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.384(16) . ?
C17A H17A 0.9500 . ?
C17A C18A 1.355(17) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.38(2) . ?
C19A H19A 0.9500 . ?
C19A C14A 1.368(16) . ?

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
C1 N3 C8 126.41(18) . . ?
N3 C1 N1 132.14(18) . . ?
N3 C1 C2 108.50(17) . . ?
N1 C1 C2 118.66(18) . . ?
C1 N1 C5 122.35(19) . . ?
C1 N1 C4 123.18(18) . . ?
C5 N1 C4 114.3(2) . . ?
C13 C8 N3 119.25(18) . . ?
C9 C8 N3 121.23(18) . . ?
C9 C8 C13 119.17(19) . . ?
O1 C2 C1 123.5(2) . . ?
O1 C2 C3 120.50(19) . . ?
C1 C2 C3 115.92(17) . . ?
C3 N4 C14B 118.6(14) . . ?
C3 N4 C14A 120.8(16) . . ?
N4 C3 C2 121.08(19) . . ?
N4 C3 N2 122.3(2) . . ?
N2 C3 C2 116.4(2) . . ?
C15B C14B N4 124.3(13) . . ?
C19B C14B N4 121.9(13) . . ?
C19B C14B C15B 113.8(12) . . ?
C8 C13 H13 120.1 . . ?
C12 C13 C8 119.9(2) . . ?
C12 C13 H13 120.1 . . ?
C3 N2 C7 118.4(3) . . ?
C3 N2 C6 122.7(3) . . ?
C6 N2 C7 118.4(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 H9 120.0 . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.6(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 C13 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C14B C15B H15B 119.6 . . ?
C16B C15B C14B 120.9(11) . . ?
C16B C15B H15B 119.6 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C14B C19B H19B 117.8 . . ?
C14B C19B C18B 124.4(12) . . ?
C18B C19B H19B 117.8 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C19B C18B H18B 120.7 . . ?
C17B C18B C19B 118.6(10) . . ?
C17B C18B H18B 120.7 . . ?
C18B C17B H17B 120.3 . . ?
C16B C17B C18B 119.5(10) . . ?
C16B C17B H17B 120.3 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C15B C16B H16B 118.6 . . ?
C17B C16B C15B 122.8(11) . . ?
C17B C16B H16B 118.6 . . ?
C16A C15A H15A 121.4 . . ?
C14A C15A H15A 121.4 . . ?
C14A C15A C16A 117.3(10) . . ?
C15A C16A H16A 119.4 . . ?
C15A C16A C17A 121.2(8) . . ?
C17A C16A H16A 119.4 . . ?
C16A C17A H17A 119.9 . . ?
C18A C17A C16A 120.2(9) . . ?
C18A C17A H17A 119.9 . . ?
C17A C18A H18A 120.4 . . ?
C17A C18A C19A 119.1(10) . . ?
C19A C18A H18A 120.4 . . ?
C18A C19A H19A 120.1 . . ?
C14A C19A C18A 119.9(13) . . ?
C14A C19A H19A 120.1 . . ?
N4 C14A C15A 117.3(14) . . ?
N4 C14A C19A 119.6(16) . . ?
C15A C14A C19A 122.2(14) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'


