# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_lrgp1
_database_code_depnum_ccdc_archive 'CCDC 1542305'
_audit_update_record             
;
2017-04-05 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_audit_creation_date             2017-03-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C54 H62 N8, 1.73(H2 O), 0.3(C H4 O)'
_chemical_formula_sum            'C54.30 H66.67 N8 O2.03'
_chemical_formula_weight         863.93
_chemical_melting_point          ?
_chemical_oxdiff_formula         C50H50O10N4
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.8264(8)
_cell_length_b                   15.4605(4)
_cell_length_c                   19.2829(9)
_cell_angle_alpha                90
_cell_angle_beta                 113.954(5)
_cell_angle_gamma                90
_cell_volume                     4856.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6361
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.0510
_cell_measurement_theta_min      1.8070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.21a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1859
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0727
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            38675
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.816
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  98.00   1.00   30.00    --   16.40  43.00 150.00  164
  2  ω    -69.00 -26.00   1.00   30.00    --   16.40  60.00   0.00   43
  3  ω     -9.00  29.00   1.00   30.00    --   16.40  60.00   0.00   38
  4  ω     58.00  90.00   1.00   30.00    --   16.40  60.00   0.00   32
  5  ω    -64.00 100.00   1.00   30.00    --   16.40  60.00-120.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0145387000
_diffrn_orient_matrix_UB_12      -0.0235618000
_diffrn_orient_matrix_UB_13      -0.0236343000
_diffrn_orient_matrix_UB_21      0.0304890000
_diffrn_orient_matrix_UB_22      -0.0196061000
_diffrn_orient_matrix_UB_23      0.0325062000
_diffrn_orient_matrix_UB_31      -0.0274879000
_diffrn_orient_matrix_UB_32      -0.0341173000
_diffrn_orient_matrix_UB_33      -0.0023593000
_diffrn_oxdiff_ac3_digest_frames 
;
010e8e9df0a22a45b1931eb8570dad493500441449d
;
_diffrn_oxdiff_ac3_digest_hkl    
;
017bc9331c9b46472759a7a6c4bbca1eddc71c
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5631
_reflns_number_total             9518
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.21a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.21a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.21a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     622
_refine_ls_number_reflns         9518
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.1275
_refine_ls_R_factor_gt           0.0741
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1020P)²+3.0970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1937
_refine_ls_wR_factor_ref         0.2234
_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, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C41B) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C43) \\sim Ueq, Uanis(C43B)
\\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C42B) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
3. Others
 Sof(O2)=Sof(H2A)=Sof(H2B)=Sof(O6)=Sof(H6A)=Sof(H6B)=FVAR(1)
 Sof(O3)=Sof(H3A)=Sof(H3B)=Sof(O4)=Sof(H4)=Sof(C61)=Sof(H61A)=Sof(H61B)=
 Sof(H61C)=FVAR(2)
 Fixed Sof: C41(0.5) H41A(0.5) H41B(0.5) H41C(0.5) C41B(0.5) H41D(0.5)
 H41E(0.5) H41F(0.5) C42(0.5) H42A(0.5) H42B(0.5) H42C(0.5) C42B(0.5) H42D(0.5)
 H42E(0.5) H42F(0.5) C43(0.5) H43A(0.5) H43B(0.5) H43C(0.5) C43B(0.5) H43D(0.5)
 H43E(0.5) H43F(0.5)
 Fixed X: O2(0.126981) H2A(0.161461) H2B(0.091801) O3(0.105981) H3A(0.16481)
 H3B(0.064429) H1A(0.277649) H1B(0.27825) O6(0.03878) H6A(0.0909) H6B(0.00502)
 Fixed Y: O2(0.198371) H2A(0.25339) H2B(0.216529) O3(0.190761) H3A(0.185121)
 H3B(0.232479) H1A(0.35767) H1B(0.272689) O6(0.324161) H6A(0.326281)
 H6B(0.32621)
 Fixed Z: O2(0.216569) H2A(0.25012) H2B(0.16921) O3(0.25606) H3A(0.29006)
 H3B(0.2484) H1A(0.321811) H1B(0.30686) O6(0.121771) H6A(0.14286) H6B(0.06975)
4.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C47(H47A,H47B), C48(H48A,H48B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C10(H10), C25(H25), C26(H26), C28(H28), C29(H29),
 C35(H35), C36(H36), C38(H38), C39(H39)
4.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C41(H41A,
 H41B,H41C), C41B(H41D,H41E,H41F), C42(H42A,H42B,H42C), C42B(H42D,H42E,H42F),
 C43(H43A,H43B,H43C), C43B(H43D,H43E,H43F), C51(H51A,H51B,H51C), C52(H52A,H52B,
 H52C), C53(H53A,H53B,H53C), C54(H54A,H54B,H54C), C61(H61A,H61B,H61C)
4.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.40569(14) 0.43145(15) 0.38861(12) 0.0321(5) Uani 1 1 d . . . . .
N2 N 0.43837(14) 0.26418(14) 0.36472(13) 0.0327(5) Uani 1 1 d . . . . .
N3 N 0.30002(15) 0.61149(17) 0.42522(15) 0.0437(6) Uani 1 1 d . . . . .
N4 N 0.23125(16) 0.63073(19) 0.43397(16) 0.0499(7) Uani 1 1 d . . . . .
N5 N 0.26006(15) 0.46400(17) 0.40125(15) 0.0431(6) Uani 1 1 d . . . . .
N6 N 0.31479(17) 0.14497(17) 0.32397(18) 0.0536(7) Uani 1 1 d . . . . .
N7 N 0.25512(17) 0.08610(19) 0.31460(18) 0.0590(8) Uani 1 1 d . . . . .
N8 N 0.41503(14) 0.03367(15) 0.36092(13) 0.0371(6) Uani 1 1 d . . . . .
C1 C 0.47798(16) 0.41457(18) 0.38380(15) 0.0299(6) Uani 1 1 d . . . . .
C2 C 0.39113(16) 0.51216(18) 0.40297(15) 0.0322(6) Uani 1 1 d . . . . .
C3 C 0.44624(17) 0.58084(18) 0.41138(15) 0.0330(6) Uani 1 1 d . . . . .
H3 H 0.4333 0.6374 0.4223 0.040 Uiso 1 1 calc R . . . .
C4 C 0.51852(16) 0.56632(17) 0.40382(15) 0.0302(6) Uani 1 1 d . . . . .
C5 C 0.53678(16) 0.48003(18) 0.39074(15) 0.0311(6) Uani 1 1 d . . . . .
C6 C 0.61296(17) 0.45581(18) 0.38695(16) 0.0345(7) Uani 1 1 d . . . . .
H6 H 0.6522 0.4993 0.3911 0.041 Uiso 1 1 calc R . . . .
C7 C 0.62984(18) 0.37313(18) 0.37765(16) 0.0347(7) Uani 1 1 d . . . . .
H7 H 0.6810 0.3594 0.3759 0.042 Uiso 1 1 calc R . . . .
C8 C 0.57264(17) 0.30502(18) 0.37036(15) 0.0321(6) Uani 1 1 d . . . . .
C9 C 0.58974(17) 0.21707(18) 0.36049(15) 0.0321(6) Uani 1 1 d . . . . .
C10 C 0.52996(17) 0.15612(18) 0.35278(16) 0.0359(7) Uani 1 1 d . . . . .
H10 H 0.5391 0.0968 0.3459 0.043 Uiso 1 1 calc R . . . .
C11 C 0.45570(17) 0.18261(18) 0.35527(15) 0.0338(6) Uani 1 1 d . . . . .
C12 C 0.49645(17) 0.32497(17) 0.37263(15) 0.0308(6) Uani 1 1 d . . . . .
C13 C 0.31212(17) 0.53015(19) 0.41039(16) 0.0351(7) Uani 1 1 d . . . . .
C14 C 0.17684(19) 0.5678(2) 0.42765(18) 0.0451(8) Uani 1 1 d . . . . .
C15 C 0.1019(2) 0.5957(3) 0.4414(2) 0.0551(9) Uani 1 1 d . . . . .
C16 C 0.0348(2) 0.5266(3) 0.4089(2) 0.0651(11) Uani 1 1 d . . . . .
H16A H -0.0083 0.5374 0.4278 0.078 Uiso 1 1 calc R . . . .
H16B H 0.0092 0.5320 0.3529 0.078 Uiso 1 1 calc R . . . .
C17 C 0.0666(2) 0.4359(3) 0.4295(2) 0.0664(11) Uani 1 1 d . . . . .
H17A H 0.0198 0.3953 0.4097 0.080 Uiso 1 1 calc R . . . .
H17B H 0.0916 0.4305 0.4855 0.080 Uiso 1 1 calc R . . . .
C18 C 0.1306(2) 0.4090(2) 0.3988(2) 0.0571(9) Uani 1 1 d . . . . .
C19 C 0.19149(18) 0.4830(2) 0.41049(18) 0.0435(8) Uani 1 1 d . . . . .
C20 C 0.1294(2) 0.6024(3) 0.5279(2) 0.0691(11) Uani 1 1 d . . . . .
H20A H 0.1558 0.5481 0.5518 0.104 Uiso 1 1 calc GR . . . .
H20B H 0.0815 0.6131 0.5395 0.104 Uiso 1 1 calc GR . . . .
H20C H 0.1685 0.6501 0.5475 0.104 Uiso 1 1 calc GR . . . .
C21 C 0.0696(2) 0.6829(3) 0.4055(2) 0.0717(11) Uani 1 1 d . . . . .
H21A H 0.1136 0.7260 0.4248 0.107 Uiso 1 1 calc GR . . . .
H21B H 0.0239 0.7006 0.4182 0.107 Uiso 1 1 calc GR . . . .
H21C H 0.0504 0.6784 0.3502 0.107 Uiso 1 1 calc GR . . . .
C22 C 0.0864(2) 0.3916(3) 0.3123(2) 0.0695(11) Uani 1 1 d . . . . .
H22A H 0.0543 0.4426 0.2870 0.104 Uiso 1 1 calc GR . . . .
H22B H 0.0496 0.3417 0.3035 0.104 Uiso 1 1 calc GR . . . .
H22C H 0.1273 0.3793 0.2916 0.104 Uiso 1 1 calc GR . . . .
C23 C 0.1755(2) 0.3280(3) 0.4376(3) 0.0789(13) Uani 1 1 d . . . . .
H23A H 0.2105 0.3080 0.4126 0.118 Uiso 1 1 calc GR . . . .
H23B H 0.1357 0.2828 0.4343 0.118 Uiso 1 1 calc GR . . . .
H23C H 0.2096 0.3406 0.4911 0.118 Uiso 1 1 calc GR . . . .
C24 C 0.57230(17) 0.64156(17) 0.40753(16) 0.0328(6) Uani 1 1 d . . . . .
C25 C 0.59478(18) 0.69895(18) 0.46843(17) 0.0371(7) Uani 1 1 d . . . . .
H25 H 0.5820 0.6857 0.5105 0.044 Uiso 1 1 calc R . . . .
C26 C 0.63549(19) 0.77490(19) 0.46815(18) 0.0440(8) Uani 1 1 d . . . . .
H26 H 0.6507 0.8125 0.5106 0.053 Uiso 1 1 calc R . . . .
C27 C 0.65485(19) 0.7980(2) 0.40796(18) 0.0448(8) Uani 1 1 d . . . . .
C28 C 0.63523(19) 0.7384(2) 0.34875(18) 0.0454(8) Uani 1 1 d . . . . .
H28 H 0.6501 0.7508 0.3077 0.054 Uiso 1 1 calc R . . . .
C29 C 0.59477(18) 0.66188(19) 0.34823(17) 0.0397(7) Uani 1 1 d . . . . .
H29 H 0.5822 0.6228 0.3070 0.048 Uiso 1 1 calc R . . . .
C30 C 0.6961(3) 0.8847(2) 0.4060(2) 0.0668(11) Uani 1 1 d . . . . .
C31 C 0.7868(3) 0.8691(4) 0.4310(5) 0.150(3) Uani 1 1 d . . . . .
H31A H 0.8107 0.8509 0.4843 0.225 Uiso 1 1 calc GR . . . .
H31B H 0.8134 0.9225 0.4255 0.225 Uiso 1 1 calc GR . . . .
H31C H 0.7954 0.8236 0.3996 0.225 Uiso 1 1 calc GR . . . .
C32 C 0.6793(4) 0.9528(3) 0.4579(3) 0.0991(17) Uani 1 1 d . . . . .
H32A H 0.6204 0.9548 0.4458 0.149 Uiso 1 1 calc GR . . . .
H32B H 0.6979 1.0099 0.4494 0.149 Uiso 1 1 calc GR . . . .
H32C H 0.7093 0.9364 0.5113 0.149 Uiso 1 1 calc GR . . . .
C33 C 0.6591(3) 0.9236(3) 0.3272(3) 0.0855(14) Uani 1 1 d . . . . .
H33A H 0.6734 0.8878 0.2924 0.128 Uiso 1 1 calc GR . . . .
H33B H 0.6807 0.9822 0.3286 0.128 Uiso 1 1 calc GR . . . .
H33C H 0.5993 0.9261 0.3095 0.128 Uiso 1 1 calc GR . . . .
C34 C 0.66945(17) 0.18993(17) 0.35933(16) 0.0336(6) Uani 1 1 d . . . . .
C35 C 0.6734(2) 0.16028(19) 0.29295(17) 0.0408(7) Uani 1 1 d . . . . .
H35 H 0.6245 0.1560 0.2480 0.049 Uiso 1 1 calc R . . . .
C36 C 0.7478(2) 0.1367(2) 0.29156(18) 0.0450(8) Uani 1 1 d . . . . .
H36 H 0.7489 0.1176 0.2452 0.054 Uiso 1 1 calc R . . . .
C37 C 0.82088(19) 0.14036(19) 0.35612(18) 0.0405(7) Uani 1 1 d . . . . .
C38 C 0.8151(2) 0.1672(2) 0.42237(19) 0.0507(8) Uani 1 1 d . . . . .
H38 H 0.8633 0.1680 0.4681 0.061 Uiso 1 1 calc R . . . .
C39 C 0.74146(19) 0.1930(2) 0.42433(18) 0.0461(8) Uani 1 1 d . . . . .
H39 H 0.7405 0.2129 0.4706 0.055 Uiso 1 1 calc R . . . .
C40 C 0.9036(2) 0.1161(2) 0.3545(2) 0.0510(8) Uani 1 1 d . . . . .
C41 C 0.9111(9) 0.0193(8) 0.3552(10) 0.108(5) Uani 0.5 1 d . U P A -2
H41A H 0.8945 -0.0049 0.3937 0.162 Uiso 0.5 1 calc GR . P A -2
H41B H 0.9682 0.0033 0.3670 0.162 Uiso 0.5 1 calc GR . P A -2
H41C H 0.8756 -0.0037 0.3052 0.162 Uiso 0.5 1 calc GR . P A -2
C41B C 0.9419(9) 0.0465(11) 0.4057(10) 0.129(6) Uani 0.5 1 d . U P A -1
H41D H 0.9327 0.0538 0.4521 0.193 Uiso 0.5 1 calc GR . P A -1
H41E H 1.0010 0.0465 0.4183 0.193 Uiso 0.5 1 calc GR . P A -1
H41F H 0.9181 -0.0086 0.3816 0.193 Uiso 0.5 1 calc GR . P A -1
C42 C 0.9128(8) 0.1527(11) 0.2868(9) 0.117(6) Uani 0.5 1 d . U P A -2
H42A H 0.8669 0.1334 0.2406 0.175 Uiso 0.5 1 calc GR . P A -2
H42B H 0.9646 0.1326 0.2859 0.175 Uiso 0.5 1 calc GR . P A -2
H42C H 0.9130 0.2160 0.2894 0.175 Uiso 0.5 1 calc GR . P A -2
C42B C 0.8909(8) 0.0925(13) 0.2731(8) 0.134(6) Uani 0.5 1 d . U P A -1
H42D H 0.8551 0.0417 0.2564 0.200 Uiso 0.5 1 calc GR . P A -1
H42E H 0.9440 0.0795 0.2717 0.200 Uiso 0.5 1 calc GR . P A -1
H42F H 0.8653 0.1413 0.2392 0.200 Uiso 0.5 1 calc GR . P A -1
C43 C 0.9789(6) 0.1491(11) 0.4254(7) 0.105(4) Uani 0.5 1 d . U P A -2
H43A H 0.9759 0.2122 0.4289 0.158 Uiso 0.5 1 calc GR . P A -2
H43B H 1.0298 0.1333 0.4205 0.158 Uiso 0.5 1 calc GR . P A -2
H43C H 0.9783 0.1226 0.4713 0.158 Uiso 0.5 1 calc GR . P A -2
C43B C 0.9571(7) 0.1946(7) 0.3752(10) 0.106(4) Uani 0.5 1 d . U P A -1
H43D H 0.9322 0.2398 0.3371 0.159 Uiso 0.5 1 calc GR . P A -1
H43E H 1.0113 0.1798 0.3770 0.159 Uiso 0.5 1 calc GR . P A -1
H43F H 0.9629 0.2157 0.4250 0.159 Uiso 0.5 1 calc GR . P A -1
C44 C 0.39114(18) 0.11662(19) 0.34643(16) 0.0359(7) Uani 1 1 d . . . . .
C45 C 0.27426(19) 0.0029(2) 0.32892(18) 0.0446(8) Uani 1 1 d . . . . .
C46 C 0.2026(2) -0.0584(2) 0.3146(2) 0.0544(9) Uani 1 1 d . . . . .
C47 C 0.2359(2) -0.1423(2) 0.3575(2) 0.0651(11) Uani 1 1 d . . . . .
H47A H 0.2528 -0.1319 0.4125 0.078 Uiso 1 1 calc R . . . .
H47B H 0.1914 -0.1860 0.3414 0.078 Uiso 1 1 calc R . . . .
C48 C 0.3075(2) -0.1779(2) 0.3449(2) 0.0630(10) Uani 1 1 d . . . . .
H48A H 0.2901 -0.1894 0.2901 0.076 Uiso 1 1 calc R . . . .
H48B H 0.3238 -0.2338 0.3720 0.076 Uiso 1 1 calc R . . . .
C49 C 0.3829(2) -0.1175(2) 0.37190(18) 0.0451(8) Uani 1 1 d . . . . .
C50 C 0.35639(18) -0.02450(19) 0.35327(16) 0.0373(7) Uani 1 1 d . . . . .
C51 C 0.1402(3) -0.0194(3) 0.3419(3) 0.0812(13) Uani 1 1 d . . . . .
H51A H 0.1676 -0.0060 0.3961 0.122 Uiso 1 1 calc GR . . . .
H51B H 0.0959 -0.0610 0.3335 0.122 Uiso 1 1 calc GR . . . .
H51C H 0.1173 0.0337 0.3134 0.122 Uiso 1 1 calc GR . . . .
C52 C 0.1607(2) -0.0736(3) 0.2276(2) 0.0661(11) Uani 1 1 d . . . . .
H52A H 0.1412 -0.0183 0.2017 0.099 Uiso 1 1 calc GR . . . .
H52B H 0.1140 -0.1130 0.2159 0.099 Uiso 1 1 calc GR . . . .
H52C H 0.2003 -0.0992 0.2102 0.099 Uiso 1 1 calc GR . . . .
C53 C 0.4299(2) -0.1237(2) 0.45801(19) 0.0593(9) Uani 1 1 d . . . . .
H53A H 0.4767 -0.0838 0.4746 0.089 Uiso 1 1 calc GR . . . .
H53B H 0.4499 -0.1829 0.4719 0.089 Uiso 1 1 calc GR . . . .
H53C H 0.3934 -0.1083 0.4827 0.089 Uiso 1 1 calc GR . . . .
C54 C 0.4394(2) -0.1440(2) 0.33349(19) 0.0497(8) Uani 1 1 d . . . . .
H54A H 0.4107 -0.1362 0.2785 0.075 Uiso 1 1 calc GR . . . .
H54B H 0.4550 -0.2048 0.3447 0.075 Uiso 1 1 calc GR . . . .
H54C H 0.4889 -0.1078 0.3526 0.075 Uiso 1 1 calc GR . . . .
O2 O 0.1270 0.1984 0.2166 0.086(5) Uiso 0.214(7) 1 d . . P B -1
H2A H 0.1615 0.2534 0.2501 0.129 Uiso 0.214(7) 1 d R . P B -1
H2B H 0.0918 0.2165 0.1692 0.129 Uiso 0.214(7) 1 d R . P B -1
O3 O 0.1060 0.1908 0.2561 0.105(5) Uiso 0.303(7) 1 d . . P C -2
H3A H 0.1648 0.1851 0.2901 0.158 Uiso 0.303(7) 1 d R . P C -2
H3B H 0.0644 0.2325 0.2484 0.158 Uiso 0.303(7) 1 d R . P C -2
O1 O 0.25175(16) 0.31998(19) 0.28461(15) 0.0747(8) Uiso 1 1 d . . . . .
H1A H 0.2776 0.3577 0.3218 0.112 Uiso 1 1 d R . . . .
H1B H 0.2782 0.2727 0.3069 0.112 Uiso 1 1 d R . . . .
O4 O 0.1415(9) 0.1691(10) 0.1307(8) 0.132(6) Uiso 0.303(7) 1 d . . P C -2
H4 H 0.1509 0.1888 0.1741 0.198 Uiso 0.303(7) 1 calc GR . P C -2
C61 C 0.1984(15) 0.1131(16) 0.1355(10) 0.152(9) Uiso 0.303(7) 1 d . . P C -2
H61A H 0.1745 0.0550 0.1248 0.228 Uiso 0.303(7) 1 calc GR . P C -2
H61B H 0.2421 0.1145 0.1868 0.228 Uiso 0.303(7) 1 calc GR . P C -2
H61C H 0.2212 0.1279 0.0986 0.228 Uiso 0.303(7) 1 calc GR . P C -2
O6 O 0.0388 0.3242 0.1218 0.101(6) Uiso 0.214(7) 1 d . . P B -1
H6A H 0.0909 0.3263 0.1429 0.152 Uiso 0.214(7) 1 d R . P B -1
H6B H 0.0050 0.3262 0.0697 0.152 Uiso 0.214(7) 1 d R . P B -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
N1 C1 1.355(3) . ?
N1 C2 1.326(4) . ?
N2 C11 1.328(4) . ?
N2 C12 1.360(3) . ?
N3 N4 1.337(3) . ?
N3 C13 1.327(4) . ?
N4 C14 1.344(4) . ?
N5 C13 1.344(4) . ?
N5 C19 1.337(4) . ?
N6 N7 1.355(4) . ?
N6 C44 1.324(4) . ?
N7 C45 1.331(4) . ?
N8 C44 1.344(4) . ?
N8 C50 1.341(4) . ?
C1 C5 1.424(4) . ?
C1 C12 1.460(4) . ?
C2 C3 1.411(4) . ?
C2 C13 1.498(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.373(4) . ?
C4 C5 1.420(4) . ?
C4 C24 1.491(4) . ?
C5 C6 1.439(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.342(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.432(4) . ?
C8 C9 1.423(4) . ?
C8 C12 1.411(4) . ?
C9 C10 1.385(4) . ?
C9 C34 1.491(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.405(4) . ?
C11 C44 1.495(4) . ?
C14 C15 1.527(4) . ?
C14 C19 1.403(5) . ?
C15 C16 1.534(5) . ?
C15 C20 1.539(5) . ?
C15 C21 1.518(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.505(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.540(5) . ?
C18 C19 1.530(5) . ?
C18 C22 1.553(5) . ?
C18 C23 1.511(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.394(4) . ?
C24 C29 1.392(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.381(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.385(4) . ?
C27 C28 1.397(5) . ?
C27 C30 1.537(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.384(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.507(7) . ?
C30 C32 1.564(6) . ?
C30 C33 1.514(6) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 C35 1.388(4) . ?
C34 C39 1.384(4) . ?
C35 H35 0.9500 . ?
C35 C36 1.387(4) . ?
C36 H36 0.9500 . ?
C36 C37 1.390(4) . ?
C37 C38 1.387(4) . ?
C37 C40 1.534(4) . ?
C38 H38 0.9500 . ?
C38 C39 1.386(4) . ?
C39 H39 0.9500 . ?
C40 C41 1.503(13) . ?
C40 C41B 1.433(12) . ?
C40 C42 1.491(11) . ?
C40 C42B 1.537(13) . ?
C40 C43 1.562(11) . ?
C40 C43B 1.493(11) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C41B H41D 0.9800 . ?
C41B H41E 0.9800 . ?
C41B H41F 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C42B H42D 0.9800 . ?
C42B H42E 0.9800 . ?
C42B H42F 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C43B H43D 0.9800 . ?
C43B H43E 0.9800 . ?
C43B H43F 0.9800 . ?
C45 C46 1.523(4) . ?
C45 C50 1.409(4) . ?
C46 C47 1.525(5) . ?
C46 C51 1.534(5) . ?
C46 C52 1.553(5) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C47 C48 1.499(5) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C48 C49 1.543(5) . ?
C49 C50 1.510(4) . ?
C49 C53 1.529(5) . ?
C49 C54 1.530(5) . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
O2 H2A 1.09409(4) . ?
O2 H2B 0.91707(6) . ?
O3 H3A 0.98942(7) . ?
O3 H3B 0.94744(3) . ?
O1 H1A 0.894(3) . ?
O1 H1B 0.882(3) . ?
O4 H4 0.8400 . ?
O4 C61 1.31(2) . ?
C61 H61A 0.9800 . ?
C61 H61B 0.9800 . ?
C61 H61C 0.9800 . ?
O6 H6A 0.85024(5) . ?
O6 H6B 0.93767(6) . ?

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 N1 C1 117.9(2) . . ?
C11 N2 C12 117.5(2) . . ?
C13 N3 N4 118.4(3) . . ?
N3 N4 C14 119.5(3) . . ?
C19 N5 C13 115.8(3) . . ?
C44 N6 N7 117.9(3) . . ?
C45 N7 N6 120.0(3) . . ?
C50 N8 C44 116.7(2) . . ?
N1 C1 C5 122.8(2) . . ?
N1 C1 C12 118.1(2) . . ?
C5 C1 C12 119.1(2) . . ?
N1 C2 C3 123.1(3) . . ?
N1 C2 C13 117.8(2) . . ?
C3 C2 C13 119.1(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 117.7(2) . . ?
C3 C4 C24 118.7(2) . . ?
C5 C4 C24 123.5(2) . . ?
C1 C5 C6 119.0(2) . . ?
C4 C5 C1 118.1(2) . . ?
C4 C5 C6 122.9(2) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.5(3) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C8 121.6(3) . . ?
C8 C7 H7 119.2 . . ?
C9 C8 C7 122.2(3) . . ?
C12 C8 C7 119.5(3) . . ?
C12 C8 C9 118.3(2) . . ?
C8 C9 C34 121.9(2) . . ?
C10 C9 C8 117.9(3) . . ?
C10 C9 C34 120.2(2) . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.5(3) . . ?
C11 C10 H10 120.2 . . ?
N2 C11 C10 123.8(3) . . ?
N2 C11 C44 116.9(2) . . ?
C10 C11 C44 119.3(3) . . ?
N2 C12 C1 117.7(2) . . ?
N2 C12 C8 123.0(2) . . ?
C8 C12 C1 119.3(2) . . ?
N3 C13 N5 125.8(3) . . ?
N3 C13 C2 116.0(3) . . ?
N5 C13 C2 118.2(3) . . ?
N4 C14 C15 115.5(3) . . ?
N4 C14 C19 120.1(3) . . ?
C19 C14 C15 124.4(3) . . ?
C14 C15 C16 108.9(3) . . ?
C14 C15 C20 106.9(3) . . ?
C16 C15 C20 110.1(3) . . ?
C21 C15 C14 111.6(3) . . ?
C21 C15 C16 110.1(3) . . ?
C21 C15 C20 109.3(3) . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 C15 113.2(3) . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C16 C17 H17A 108.7 . . ?
C16 C17 H17B 108.7 . . ?
C16 C17 C18 114.1(3) . . ?
H17A C17 H17B 107.6 . . ?
C18 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C17 C18 C22 109.2(3) . . ?
C19 C18 C17 109.5(3) . . ?
C19 C18 C22 107.9(3) . . ?
C23 C18 C17 111.1(3) . . ?
C23 C18 C19 110.2(3) . . ?
C23 C18 C22 108.9(4) . . ?
N5 C19 C14 120.3(3) . . ?
N5 C19 C18 116.7(3) . . ?
C14 C19 C18 123.0(3) . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C21 H21A 109.5 . . ?
C15 C21 H21B 109.5 . . ?
C15 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C4 119.8(2) . . ?
C29 C24 C4 122.0(3) . . ?
C29 C24 C25 117.9(3) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.6(3) . . ?
C26 C25 H25 119.7 . . ?
C25 C26 H26 118.9 . . ?
C25 C26 C27 122.2(3) . . ?
C27 C26 H26 118.9 . . ?
C26 C27 C28 116.7(3) . . ?
C26 C27 C30 122.1(3) . . ?
C28 C27 C30 121.2(3) . . ?
C27 C28 H28 119.1 . . ?
C29 C28 C27 121.8(3) . . ?
C29 C28 H28 119.1 . . ?
C24 C29 H29 119.7 . . ?
C28 C29 C24 120.7(3) . . ?
C28 C29 H29 119.7 . . ?
C27 C30 C32 110.7(3) . . ?
C31 C30 C27 108.3(3) . . ?
C31 C30 C32 111.2(5) . . ?
C31 C30 C33 111.0(4) . . ?
C33 C30 C27 110.7(3) . . ?
C33 C30 C32 104.9(4) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C35 C34 C9 120.8(3) . . ?
C39 C34 C9 121.1(3) . . ?
C39 C34 C35 118.1(3) . . ?
C34 C35 H35 119.6 . . ?
C34 C35 C36 120.8(3) . . ?
C36 C35 H35 119.6 . . ?
C35 C36 H36 119.1 . . ?
C35 C36 C37 121.9(3) . . ?
C37 C36 H36 119.1 . . ?
C36 C37 C40 122.1(3) . . ?
C38 C37 C36 116.4(3) . . ?
C38 C37 C40 121.6(3) . . ?
C37 C38 H38 118.8 . . ?
C39 C38 C37 122.5(3) . . ?
C39 C38 H38 118.8 . . ?
C34 C39 C38 120.4(3) . . ?
C34 C39 H39 119.8 . . ?
C38 C39 H39 119.8 . . ?
C37 C40 C42B 109.5(5) . . ?
C37 C40 C43 113.2(5) . . ?
C41 C40 C37 109.0(6) . . ?
C41 C40 C43 106.0(9) . . ?
C41B C40 C37 111.2(6) . . ?
C41B C40 C42B 110.9(10) . . ?
C41B C40 C43B 110.7(10) . . ?
C42 C40 C37 111.9(6) . . ?
C42 C40 C41 110.1(10) . . ?
C42 C40 C43 106.4(8) . . ?
C43B C40 C37 108.1(5) . . ?
C43B C40 C42B 106.2(9) . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C40 C41B H41D 109.5 . . ?
C40 C41B H41E 109.5 . . ?
C40 C41B H41F 109.5 . . ?
H41D C41B H41E 109.5 . . ?
H41D C41B H41F 109.5 . . ?
H41E C41B H41F 109.5 . . ?
C40 C42 H42A 109.5 . . ?
C40 C42 H42B 109.5 . . ?
C40 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C40 C42B H42D 109.5 . . ?
C40 C42B H42E 109.5 . . ?
C40 C42B H42F 109.5 . . ?
H42D C42B H42E 109.5 . . ?
H42D C42B H42F 109.5 . . ?
H42E C42B H42F 109.5 . . ?
C40 C43 H43A 109.5 . . ?
C40 C43 H43B 109.5 . . ?
C40 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C40 C43B H43D 109.5 . . ?
C40 C43B H43E 109.5 . . ?
C40 C43B H43F 109.5 . . ?
H43D C43B H43E 109.5 . . ?
H43D C43B H43F 109.5 . . ?
H43E C43B H43F 109.5 . . ?
N6 C44 N8 125.5(3) . . ?
N6 C44 C11 116.9(3) . . ?
N8 C44 C11 117.6(3) . . ?
N7 C45 C46 116.0(3) . . ?
N7 C45 C50 120.3(3) . . ?
C50 C45 C46 123.7(3) . . ?
C45 C46 C51 111.4(3) . . ?
C45 C46 C52 106.9(3) . . ?
C47 C46 C45 108.6(3) . . ?
C47 C46 C51 109.0(3) . . ?
C47 C46 C52 111.6(3) . . ?
C51 C46 C52 109.4(3) . . ?
C46 C47 H47A 108.9 . . ?
C46 C47 H47B 108.9 . . ?
H47A C47 H47B 107.8 . . ?
C48 C47 C46 113.2(3) . . ?
C48 C47 H47A 108.9 . . ?
C48 C47 H47B 108.9 . . ?
C47 C48 H48A 108.8 . . ?
C47 C48 H48B 108.8 . . ?
C47 C48 C49 114.0(3) . . ?
H48A C48 H48B 107.7 . . ?
C49 C48 H48A 108.8 . . ?
C49 C48 H48B 108.8 . . ?
C50 C49 C48 110.5(3) . . ?
C50 C49 C53 107.4(3) . . ?
C50 C49 C54 110.1(3) . . ?
C53 C49 C48 110.3(3) . . ?
C54 C49 C48 109.2(3) . . ?
C54 C49 C53 109.3(3) . . ?
N8 C50 C45 119.5(3) . . ?
N8 C50 C49 117.2(3) . . ?
C45 C50 C49 123.2(3) . . ?
C46 C51 H51A 109.5 . . ?
C46 C51 H51B 109.5 . . ?
C46 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C46 C52 H52A 109.5 . . ?
C46 C52 H52B 109.5 . . ?
C46 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C49 C53 H53A 109.5 . . ?
C49 C53 H53B 109.5 . . ?
C49 C53 H53C 109.5 . . ?
H53A C53 H53B 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C49 C54 H54A 109.5 . . ?
C49 C54 H54B 109.5 . . ?
C49 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
H2A O2 H2B 110.103(4) . . ?
H3A O3 H3B 135.606(2) . . ?
H1A O1 H1B 98.6(3) . . ?
C61 O4 H4 109.5 . . ?
O4 C61 H61A 109.5 . . ?
O4 C61 H61B 109.5 . . ?
O4 C61 H61C 109.5 . . ?
H61A C61 H61B 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
H6A O6 H6B 127.769(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.851
_oxdiff_exptl_absorpt_empirical_full_min 0.494
####################################################################### 
# 
# 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_s4531ma_a
_database_code_depnum_ccdc_archive 'CCDC 1542302'
_audit_update_record             
;
2017-04-05 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------# 

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '4,7-Me-CyMe4-BTPhen Eu(NO3)3 Complex'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H45 Eu N12 O9'
_chemical_formula_weight         965.82

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'
Eu Eu -8.9294 11.1857 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.6829(5)
_cell_length_b                   11.9538(5)
_cell_length_c                   17.4933(8)
_cell_angle_alpha                88.385(3)
_cell_angle_beta                 77.936(3)
_cell_angle_gamma                70.385(3)
_cell_volume                     2055.67(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8911
_cell_measurement_theta_min      4.50
_cell_measurement_theta_max      72.10

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    11.506
_shelx_estimated_absorpt_T_min   0.277
_shelx_estimated_absorpt_T_max   0.656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.543359
_exptl_absorpt_correction_T_max  0.656
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18822
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.930
_diffrn_reflns_theta_max         72.233
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             7668
_reflns_number_gt                7171
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0602P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7668
_refine_ls_number_parameters     552
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3604(3) 0.8852(3) 0.47106(17) 0.0194(6) Uani 1 1 d . . . . .
C2 C 0.5059(3) 0.7135(3) 0.54710(17) 0.0194(6) Uani 1 1 d . . . . .
C3 C 0.4883(3) 0.8049(3) 0.43198(18) 0.0206(6) Uani 1 1 d . . . . .
C4 C 0.5480(3) 0.8126(3) 0.34636(17) 0.0228(6) Uani 1 1 d . . . . .
C5 C 0.4325(4) 0.8798(3) 0.30472(18) 0.0291(7) Uani 1 1 d . . . . .
H5A H 0.4728 0.8972 0.2514 0.035 Uiso 1 1 calc R U . . .
H5B H 0.3793 0.8278 0.2994 0.035 Uiso 1 1 calc R U . . .
C6 C 0.3376(4) 0.9948(3) 0.34727(19) 0.0279(7) Uani 1 1 d . . . . .
H6A H 0.2686 1.0346 0.3163 0.034 Uiso 1 1 calc R U . . .
H6B H 0.3902 1.0479 0.3512 0.034 Uiso 1 1 calc R U . . .
C7 C 0.2650(3) 0.9771(3) 0.42972(18) 0.0229(6) Uani 1 1 d . . . . .
C8 C 0.6508(4) 0.8778(3) 0.34266(19) 0.0277(7) Uani 1 1 d . . . . .
H8A H 0.6038 0.9579 0.3670 0.042 Uiso 1 1 calc R U . . .
H8B H 0.6927 0.8835 0.2879 0.042 Uiso 1 1 calc R U . . .
H8C H 0.7213 0.8338 0.3707 0.042 Uiso 1 1 calc R U . . .
C9 C 0.6214(4) 0.6875(3) 0.30879(18) 0.0290(7) Uani 1 1 d . . . . .
H9A H 0.7031 0.6495 0.3297 0.043 Uiso 1 1 calc R U . . .
H9B H 0.6474 0.6924 0.2520 0.043 Uiso 1 1 calc R U . . .
H9C H 0.5608 0.6405 0.3206 0.043 Uiso 1 1 calc R U . . .
C10 C 0.1496(4) 0.9273(3) 0.4249(2) 0.0304(7) Uani 1 1 d . . . . .
H10A H 0.1871 0.8547 0.3911 0.046 Uiso 1 1 calc R U . . .
H10B H 0.0792 0.9868 0.4032 0.046 Uiso 1 1 calc R U . . .
H10C H 0.1098 0.9091 0.4775 0.046 Uiso 1 1 calc R U . . .
C11 C 0.2026(4) 1.0963(3) 0.4769(2) 0.0294(7) Uani 1 1 d . . . . .
H11A H 0.1577 1.0841 0.5298 0.044 Uiso 1 1 calc R U . . .
H11B H 0.1357 1.1523 0.4511 0.044 Uiso 1 1 calc R U . . .
H11C H 0.2745 1.1286 0.4801 0.044 Uiso 1 1 calc R U . . .
C12 C 0.5801(3) 0.6146(3) 0.59142(17) 0.0196(6) Uani 1 1 d . . . . .
C13 C 0.5801(3) 0.5129(2) 0.70532(17) 0.0178(5) Uani 1 1 d . . . . .
C14 C 0.5095(3) 0.5016(2) 0.78383(17) 0.0164(5) Uani 1 1 d . . . . .
C15 C 0.3219(3) 0.5758(2) 0.88316(17) 0.0168(5) Uani 1 1 d . . . . .
C16 C 0.3763(3) 0.4881(2) 0.93331(17) 0.0185(5) Uani 1 1 d . . . . .
H16 H 0.3273 0.4877 0.9853 0.022 Uiso 1 1 calc R U . . .
C17 C 0.5015(3) 0.4023(2) 0.90675(18) 0.0195(6) Uani 1 1 d . . . . .
C18 C 0.5719(3) 0.4084(2) 0.82929(18) 0.0184(5) Uani 1 1 d . . . . .
C19 C 0.7033(3) 0.3259(3) 0.79583(19) 0.0232(6) Uani 1 1 d . . . . .
H19 H 0.7436 0.2603 0.8250 0.028 Uiso 1 1 calc R U . . .
C20 C 0.7715(3) 0.3391(3) 0.72351(19) 0.0230(6) Uani 1 1 d . . . . .
H20 H 0.8603 0.2845 0.7041 0.028 Uiso 1 1 calc R U . . .
C21 C 0.7132(3) 0.4329(3) 0.67581(18) 0.0198(6) Uani 1 1 d . . . . .
C22 C 0.7808(3) 0.4498(3) 0.59961(19) 0.0218(6) Uani 1 1 d . . . . .
C23 C 0.7122(3) 0.5411(3) 0.55787(18) 0.0220(6) Uani 1 1 d . . . . .
H23 H 0.7544 0.5541 0.5066 0.026 Uiso 1 1 calc R U . . .
C24 C 0.5600(3) 0.3046(3) 0.95820(19) 0.0247(6) Uani 1 1 d . . . . .
H24A H 0.5009 0.3188 1.0105 0.037 Uiso 1 1 calc R U . . .
H24B H 0.6508 0.3030 0.9619 0.037 Uiso 1 1 calc R U . . .
H24C H 0.5663 0.2281 0.9358 0.037 Uiso 1 1 calc R U . . .
C25 C 0.9241(3) 0.3722(3) 0.5648(2) 0.0287(7) Uani 1 1 d . . . . .
H25A H 0.9501 0.3934 0.5107 0.043 Uiso 1 1 calc R U . . .
H25B H 0.9297 0.2887 0.5655 0.043 Uiso 1 1 calc R U . . .
H25C H 0.9859 0.3840 0.5956 0.043 Uiso 1 1 calc R U . . .
C26 C 0.1840(3) 0.6664(2) 0.90993(17) 0.0165(5) Uani 1 1 d . . . . .
C27 C -0.0607(3) 0.8244(2) 0.95085(17) 0.0165(5) Uani 1 1 d . . . . .
C28 C -0.2002(3) 0.9197(3) 0.97119(17) 0.0198(6) Uani 1 1 d . . . . .
C29 C -0.2889(3) 0.8775(3) 1.03806(19) 0.0268(6) Uani 1 1 d . . . . .
H29A H -0.3759 0.9430 1.0562 0.032 Uiso 1 1 calc R U . . .
H29B H -0.3099 0.8105 1.0183 0.032 Uiso 1 1 calc R U . . .
C30 C -0.2202(3) 0.8378(3) 1.10673(18) 0.0269(7) Uani 1 1 d . . . . .
H30A H -0.2844 0.8172 1.1496 0.032 Uiso 1 1 calc R U . . .
H30B H -0.1991 0.9048 1.1262 0.032 Uiso 1 1 calc R U . . .
C31 C -0.0878(3) 0.7296(3) 1.08574(17) 0.0214(6) Uani 1 1 d . . . . .
C32 C -0.0081(3) 0.7397(3) 1.00470(17) 0.0182(5) Uani 1 1 d . . . . .
C33 C -0.2679(3) 0.9437(3) 0.9004(2) 0.0280(7) Uani 1 1 d . . . . .
H33A H -0.2106 0.9695 0.8573 0.042 Uiso 1 1 calc R U . . .
H33B H -0.3571 1.0061 0.9149 0.042 Uiso 1 1 calc R U . . .
H33C H -0.2794 0.8707 0.8839 0.042 Uiso 1 1 calc R U . . .
C34 C -0.1803(3) 1.0348(3) 0.99505(19) 0.0252(6) Uani 1 1 d . . . . .
H34A H -0.1259 1.0180 1.0354 0.038 Uiso 1 1 calc R U . . .
H34B H -0.2692 1.0947 1.0157 0.038 Uiso 1 1 calc R U . . .
H34C H -0.1332 1.0647 0.9492 0.038 Uiso 1 1 calc R U . . .
C35 C -0.1185(4) 0.6132(3) 1.0827(2) 0.0299(7) Uani 1 1 d . . . . .
H35A H -0.1666 0.6150 1.0405 0.045 Uiso 1 1 calc R U . . .
H35B H -0.1753 0.6047 1.1327 0.045 Uiso 1 1 calc R U . . .
H35C H -0.0330 0.5459 1.0729 0.045 Uiso 1 1 calc R U . . .
C36 C -0.0031(4) 0.7211(3) 1.14726(18) 0.0281(7) Uani 1 1 d . . . . .
H36A H 0.0786 0.6503 1.1355 0.042 Uiso 1 1 calc R U . . .
H36B H -0.0569 0.7156 1.1991 0.042 Uiso 1 1 calc R U . . .
H36C H 0.0235 0.7921 1.1468 0.042 Uiso 1 1 calc R U . . .
C37 C 0.8130(4) 0.6895(3) 0.7449(2) 0.0354(8) Uani 1 1 d . . . . .
H37A H 0.7322 0.7319 0.7241 0.053 Uiso 1 1 calc R U . . .
H37B H 0.8746 0.6250 0.7077 0.053 Uiso 1 1 calc R U . . .
H37C H 0.8595 0.7448 0.7530 0.053 Uiso 1 1 calc R U . . .
C38 C 0.7720(4) 0.6398(3) 0.8195(2) 0.0383(8) Uani 1 1 d . . . . .
Eu1 Eu 0.28164(2) 0.74943(2) 0.72455(2) 0.01247(7) Uani 1 1 d . . . . .
N1 N 0.3144(3) 0.8762(2) 0.54696(15) 0.0197(5) Uani 1 1 d . . . . .
N2 N 0.3875(3) 0.7895(2) 0.58594(14) 0.0184(5) Uani 1 1 d . . . . .
N3 N 0.5601(3) 0.7198(2) 0.47164(15) 0.0212(5) Uani 1 1 d . . . . .
N4 N 0.5151(2) 0.6018(2) 0.66312(14) 0.0167(5) Uani 1 1 d . . . . .
N5 N 0.3849(2) 0.5828(2) 0.81023(14) 0.0163(5) Uani 1 1 d . . . . .
N6 N 0.1372(2) 0.7446(2) 0.85911(14) 0.0160(5) Uani 1 1 d . . . . .
N7 N 0.0132(3) 0.8257(2) 0.87984(14) 0.0180(5) Uani 1 1 d . . . . .
N8 N 0.1169(3) 0.6608(2) 0.98311(14) 0.0185(5) Uani 1 1 d . . . . .
N9 N 0.1680(3) 0.5904(2) 0.65676(15) 0.0215(5) Uani 1 1 d . . . . .
N10 N 0.4439(3) 0.8578(2) 0.79529(15) 0.0204(5) Uani 1 1 d . . . . .
N11 N 0.0475(3) 0.9627(2) 0.73173(16) 0.0236(5) Uani 1 1 d . . . . .
N12 N 0.7396(5) 0.6024(3) 0.8766(2) 0.0569(11) Uani 1 1 d . . . . .
O1 O 0.2419(2) 0.6407(2) 0.61368(13) 0.0272(5) Uani 1 1 d . . . . .
O2 O 0.1582(2) 0.60163(19) 0.73032(13) 0.0236(4) Uani 1 1 d . . . . .
O3 O 0.1095(3) 0.5340(2) 0.62983(14) 0.0307(5) Uani 1 1 d . . . . .
O4 O 0.4652(2) 0.8348(2) 0.72171(13) 0.0252(4) Uani 1 1 d . . . . .
O5 O 0.3519(2) 0.8264(2) 0.83752(13) 0.0244(4) Uani 1 1 d . . . . .
O6 O 0.5097(3) 0.9067(2) 0.82233(15) 0.0313(5) Uani 1 1 d . . . . .
O7 O 0.0528(2) 0.86463(19) 0.70162(13) 0.0243(4) Uani 1 1 d . . . . .
O8 O 0.1577(2) 0.96272(19) 0.74963(14) 0.0269(5) Uani 1 1 d . . . . .
O9 O -0.0545(3) 1.0492(2) 0.74323(16) 0.0346(6) 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
C1 N1 1.331(4) . ?
C1 C3 1.422(4) . ?
C1 C7 1.510(4) . ?
C2 N3 1.337(4) . ?
C2 N2 1.338(4) . ?
C2 C12 1.484(4) . ?
C3 N3 1.329(4) . ?
C3 C4 1.514(4) . ?
C4 C9 1.528(4) . ?
C4 C8 1.536(4) . ?
C4 C5 1.542(5) . ?
C5 C6 1.509(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.534(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C11 1.534(4) . ?
C7 C10 1.555(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N4 1.332(4) . ?
C12 C23 1.399(4) . ?
C13 N4 1.353(4) . ?
C13 C21 1.417(4) . ?
C13 C14 1.449(4) . ?
C14 N5 1.352(4) . ?
C14 C18 1.411(4) . ?
C15 N5 1.327(4) . ?
C15 C16 1.399(4) . ?
C15 C26 1.494(4) . ?
C16 C17 1.380(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.418(4) . ?
C17 C24 1.500(4) . ?
C18 C19 1.431(4) . ?
C19 C20 1.355(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.428(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.421(4) . ?
C22 C23 1.380(4) . ?
C22 C25 1.505(4) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 N6 1.319(4) . ?
C26 N8 1.342(4) . ?
C27 N7 1.328(4) . ?
C27 C32 1.419(4) . ?
C27 C28 1.519(4) . ?
C28 C33 1.534(4) . ?
C28 C29 1.531(5) . ?
C28 C34 1.542(4) . ?
C29 C30 1.519(5) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.546(4) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C36 1.525(5) . ?
C31 C32 1.518(4) . ?
C31 C35 1.537(4) . ?
C32 N8 1.334(4) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C38 1.462(6) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 N12 1.119(6) . ?
Eu1 O8 2.450(2) . ?
Eu1 O7 2.481(2) . ?
Eu1 O4 2.488(2) . ?
Eu1 O2 2.524(2) . ?
Eu1 N6 2.541(2) . ?
Eu1 N5 2.545(2) . ?
Eu1 O1 2.547(2) . ?
Eu1 O5 2.550(2) . ?
Eu1 N4 2.554(2) . ?
Eu1 N2 2.557(2) . ?
Eu1 N11 2.895(3) . ?
Eu1 N10 2.951(3) . ?
N1 N2 1.337(4) . ?
N6 N7 1.335(3) . ?
N9 O3 1.221(4) . ?
N9 O1 1.264(4) . ?
N9 O2 1.276(4) . ?
N10 O6 1.222(4) . ?
N10 O5 1.257(4) . ?
N10 O4 1.280(3) . ?
N11 O9 1.208(4) . ?
N11 O8 1.280(4) . ?
N11 O7 1.278(4) . ?

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
N1 C1 C3 120.2(3) . . ?
N1 C1 C7 116.2(3) . . ?
C3 C1 C7 123.4(3) . . ?
N3 C2 N2 124.7(3) . . ?
N3 C2 C12 118.4(3) . . ?
N2 C2 C12 117.0(3) . . ?
N3 C3 C1 119.4(3) . . ?
N3 C3 C4 117.9(3) . . ?
C1 C3 C4 122.7(3) . . ?
C3 C4 C9 109.7(2) . . ?
C3 C4 C8 107.1(3) . . ?
C9 C4 C8 109.5(3) . . ?
C3 C4 C5 109.1(3) . . ?
C9 C4 C5 109.7(3) . . ?
C8 C4 C5 111.7(3) . . ?
C6 C5 C4 113.3(3) . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C5 C6 C7 113.1(3) . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C1 C7 C6 111.2(3) . . ?
C1 C7 C11 111.1(3) . . ?
C6 C7 C11 109.9(3) . . ?
C1 C7 C10 105.5(3) . . ?
C6 C7 C10 110.2(3) . . ?
C11 C7 C10 108.8(3) . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N4 C12 C23 123.2(3) . . ?
N4 C12 C2 116.7(3) . . ?
C23 C12 C2 120.0(3) . . ?
N4 C13 C21 122.6(3) . . ?
N4 C13 C14 117.6(3) . . ?
C21 C13 C14 119.8(3) . . ?
N5 C14 C18 122.9(3) . . ?
N5 C14 C13 117.5(3) . . ?
C18 C14 C13 119.7(3) . . ?
N5 C15 C16 123.6(3) . . ?
N5 C15 C26 116.2(2) . . ?
C16 C15 C26 120.2(3) . . ?
C17 C16 C15 119.5(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 118.0(3) . . ?
C16 C17 C24 120.7(3) . . ?
C18 C17 C24 121.3(3) . . ?
C14 C18 C17 118.1(3) . . ?
C14 C18 C19 118.8(3) . . ?
C17 C18 C19 123.1(3) . . ?
C20 C19 C18 121.5(3) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C21 121.6(3) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C13 C21 C22 118.0(3) . . ?
C13 C21 C20 118.5(3) . . ?
C22 C21 C20 123.5(3) . . ?
C23 C22 C21 118.3(3) . . ?
C23 C22 C25 120.1(3) . . ?
C21 C22 C25 121.6(3) . . ?
C22 C23 C12 119.7(3) . . ?
C22 C23 H23 120.1 . . ?
C12 C23 H23 120.1 . . ?
C17 C24 H24A 109.5 . . ?
C17 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C17 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N6 C26 N8 125.2(3) . . ?
N6 C26 C15 117.1(3) . . ?
N8 C26 C15 117.6(3) . . ?
N7 C27 C32 120.7(3) . . ?
N7 C27 C28 116.5(3) . . ?
C32 C27 C28 122.7(3) . . ?
C27 C28 C33 111.1(2) . . ?
C27 C28 C29 108.6(3) . . ?
C33 C28 C29 109.4(3) . . ?
C27 C28 C34 107.5(2) . . ?
C33 C28 C34 108.6(3) . . ?
C29 C28 C34 111.7(3) . . ?
C30 C29 C28 112.4(3) . . ?
C30 C29 H29A 109.1 . . ?
C28 C29 H29A 109.1 . . ?
C30 C29 H29B 109.1 . . ?
C28 C29 H29B 109.1 . . ?
H29A C29 H29B 107.9 . . ?
C29 C30 C31 113.2(3) . . ?
C29 C30 H30A 108.9 . . ?
C31 C30 H30A 108.9 . . ?
C29 C30 H30B 108.9 . . ?
C31 C30 H30B 108.9 . . ?
H30A C30 H30B 107.7 . . ?
C36 C31 C32 111.0(3) . . ?
C36 C31 C35 108.7(3) . . ?
C32 C31 C35 105.9(2) . . ?
C36 C31 C30 109.5(3) . . ?
C32 C31 C30 110.5(2) . . ?
C35 C31 C30 111.3(3) . . ?
N8 C32 C27 119.2(3) . . ?
N8 C32 C31 116.9(3) . . ?
C27 C32 C31 123.9(3) . . ?
C28 C33 H33A 109.5 . . ?
C28 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C28 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C28 C34 H34A 109.5 . . ?
C28 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C28 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C31 C35 H35A 109.5 . . ?
C31 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C31 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C31 C36 H36A 109.5 . . ?
C31 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C31 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C38 C37 H37A 109.5 . . ?
C38 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C38 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N12 C38 C37 179.4(5) . . ?
O8 Eu1 O7 51.97(7) . . ?
O8 Eu1 O4 76.61(8) . . ?
O7 Eu1 O4 124.01(8) . . ?
O8 Eu1 O2 121.39(8) . . ?
O7 Eu1 O2 74.49(7) . . ?
O4 Eu1 O2 161.34(8) . . ?
O8 Eu1 N6 80.66(8) . . ?
O7 Eu1 N6 79.94(8) . . ?
O4 Eu1 N6 115.47(7) . . ?
O2 Eu1 N6 66.91(7) . . ?
O8 Eu1 N5 133.38(8) . . ?
O7 Eu1 N5 137.75(8) . . ?
O4 Eu1 N5 92.07(8) . . ?
O2 Eu1 N5 72.12(7) . . ?
N6 Eu1 N5 63.60(8) . . ?
O8 Eu1 O1 119.21(8) . . ?
O7 Eu1 O1 72.85(7) . . ?
O4 Eu1 O1 128.08(7) . . ?
O2 Eu1 O1 50.30(7) . . ?
N6 Eu1 O1 115.83(7) . . ?
N5 Eu1 O1 103.48(8) . . ?
O8 Eu1 O5 70.08(8) . . ?
O7 Eu1 O5 116.02(7) . . ?
O4 Eu1 O5 50.52(7) . . ?
O2 Eu1 O5 127.23(7) . . ?
N6 Eu1 O5 64.99(7) . . ?
N5 Eu1 O5 68.16(7) . . ?
O1 Eu1 O5 170.66(8) . . ?
O8 Eu1 N4 141.97(8) . . ?
O7 Eu1 N4 144.83(7) . . ?
O4 Eu1 N4 68.37(7) . . ?
O2 Eu1 N4 95.18(7) . . ?
N6 Eu1 N4 127.52(8) . . ?
N5 Eu1 N4 63.96(8) . . ?
O1 Eu1 N4 74.84(8) . . ?
O5 Eu1 N4 97.18(8) . . ?
O8 Eu1 N2 89.80(8) . . ?
O7 Eu1 N2 89.63(8) . . ?
O4 Eu1 N2 67.30(8) . . ?
O2 Eu1 N2 114.27(7) . . ?
N6 Eu1 N2 168.83(8) . . ?
N5 Eu1 N2 127.57(8) . . ?
O1 Eu1 N2 63.99(8) . . ?
O5 Eu1 N2 117.20(8) . . ?
N4 Eu1 N2 63.64(8) . . ?
O8 Eu1 N11 26.04(8) . . ?
O7 Eu1 N11 26.08(8) . . ?
O4 Eu1 N11 101.29(8) . . ?
O2 Eu1 N11 97.27(8) . . ?
N6 Eu1 N11 77.16(8) . . ?
N5 Eu1 N11 140.52(8) . . ?
O1 Eu1 N11 97.07(8) . . ?
O5 Eu1 N11 92.18(8) . . ?
N4 Eu1 N11 155.25(8) . . ?
N2 Eu1 N11 91.71(8) . . ?
O8 Eu1 N10 70.79(7) . . ?
O7 Eu1 N10 122.72(7) . . ?
O4 Eu1 N10 25.46(7) . . ?
O2 Eu1 N10 149.44(7) . . ?
N6 Eu1 N10 90.01(7) . . ?
N5 Eu1 N10 79.86(7) . . ?
O1 Eu1 N10 152.87(7) . . ?
O5 Eu1 N10 25.08(7) . . ?
N4 Eu1 N10 82.98(7) . . ?
N2 Eu1 N10 92.33(8) . . ?
N11 Eu1 N10 96.66(7) . . ?
C1 N1 N2 119.7(3) . . ?
N1 N2 C2 118.7(3) . . ?
N1 N2 Eu1 119.59(18) . . ?
C2 N2 Eu1 120.78(19) . . ?
C3 N3 C2 117.3(3) . . ?
C12 N4 C13 118.2(3) . . ?
C12 N4 Eu1 121.41(19) . . ?
C13 N4 Eu1 120.18(19) . . ?
C15 N5 C14 117.8(2) . . ?
C15 N5 Eu1 121.50(19) . . ?
C14 N5 Eu1 120.66(19) . . ?
C26 N6 N7 119.3(2) . . ?
C26 N6 Eu1 121.38(19) . . ?
N7 N6 Eu1 119.29(17) . . ?
C27 N7 N6 119.1(2) . . ?
C26 N8 C32 116.5(3) . . ?
O3 N9 O1 122.2(3) . . ?
O3 N9 O2 121.7(3) . . ?
O1 N9 O2 116.1(2) . . ?
O3 N9 Eu1 173.7(2) . . ?
O1 N9 Eu1 58.76(14) . . ?
O2 N9 Eu1 57.77(14) . . ?
O6 N10 O5 122.5(3) . . ?
O6 N10 O4 121.6(3) . . ?
O5 N10 O4 115.9(2) . . ?
O6 N10 Eu1 177.1(2) . . ?
O5 N10 Eu1 59.33(14) . . ?
O4 N10 Eu1 56.65(14) . . ?
O9 N11 O8 122.2(3) . . ?
O9 N11 O7 122.6(3) . . ?
O8 N11 O7 115.2(2) . . ?
O9 N11 Eu1 172.8(2) . . ?
O8 N11 Eu1 57.17(14) . . ?
O7 N11 Eu1 58.56(14) . . ?
N9 O1 Eu1 96.14(17) . . ?
N9 O2 Eu1 96.91(17) . . ?
N10 O4 Eu1 97.89(17) . . ?
N10 O5 Eu1 95.59(16) . . ?
N11 O7 Eu1 95.36(17) . . ?
N11 O8 Eu1 96.79(16) . . ?

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
N1 C1 C3 N3 1.1(4) . . . . ?
C7 C1 C3 N3 -173.7(3) . . . . ?
N1 C1 C3 C4 -178.3(3) . . . . ?
C7 C1 C3 C4 6.9(5) . . . . ?
N3 C3 C4 C9 37.9(4) . . . . ?
C1 C3 C4 C9 -142.7(3) . . . . ?
N3 C3 C4 C8 -80.8(3) . . . . ?
C1 C3 C4 C8 98.6(3) . . . . ?
N3 C3 C4 C5 158.1(3) . . . . ?
C1 C3 C4 C5 -22.5(4) . . . . ?
C3 C4 C5 C6 48.7(4) . . . . ?
C9 C4 C5 C6 168.9(3) . . . . ?
C8 C4 C5 C6 -69.6(3) . . . . ?
C4 C5 C6 C7 -61.0(4) . . . . ?
N1 C1 C7 C6 169.8(3) . . . . ?
C3 C1 C7 C6 -15.1(4) . . . . ?
N1 C1 C7 C11 47.0(4) . . . . ?
C3 C1 C7 C11 -137.9(3) . . . . ?
N1 C1 C7 C10 -70.7(3) . . . . ?
C3 C1 C7 C10 104.3(3) . . . . ?
C5 C6 C7 C1 41.0(4) . . . . ?
C5 C6 C7 C11 164.5(3) . . . . ?
C5 C6 C7 C10 -75.6(4) . . . . ?
N3 C2 C12 N4 -171.4(3) . . . . ?
N2 C2 C12 N4 7.8(4) . . . . ?
N3 C2 C12 C23 9.2(4) . . . . ?
N2 C2 C12 C23 -171.6(3) . . . . ?
N4 C13 C14 N5 -1.8(4) . . . . ?
C21 C13 C14 N5 177.6(3) . . . . ?
N4 C13 C14 C18 178.4(3) . . . . ?
C21 C13 C14 C18 -2.2(4) . . . . ?
N5 C15 C16 C17 -0.7(4) . . . . ?
C26 C15 C16 C17 177.5(3) . . . . ?
C15 C16 C17 C18 1.4(4) . . . . ?
C15 C16 C17 C24 -177.7(3) . . . . ?
N5 C14 C18 C17 -1.7(4) . . . . ?
C13 C14 C18 C17 178.1(2) . . . . ?
N5 C14 C18 C19 179.2(3) . . . . ?
C13 C14 C18 C19 -1.0(4) . . . . ?
C16 C17 C18 C14 -0.2(4) . . . . ?
C24 C17 C18 C14 178.9(3) . . . . ?
C16 C17 C18 C19 178.8(3) . . . . ?
C24 C17 C18 C19 -2.1(4) . . . . ?
C14 C18 C19 C20 3.6(4) . . . . ?
C17 C18 C19 C20 -175.5(3) . . . . ?
C18 C19 C20 C21 -2.8(5) . . . . ?
N4 C13 C21 C22 1.6(4) . . . . ?
C14 C13 C21 C22 -177.7(3) . . . . ?
N4 C13 C21 C20 -177.6(3) . . . . ?
C14 C13 C21 C20 3.0(4) . . . . ?
C19 C20 C21 C13 -0.5(4) . . . . ?
C19 C20 C21 C22 -179.8(3) . . . . ?
C13 C21 C22 C23 -1.6(4) . . . . ?
C20 C21 C22 C23 177.7(3) . . . . ?
C13 C21 C22 C25 177.6(3) . . . . ?
C20 C21 C22 C25 -3.2(5) . . . . ?
C21 C22 C23 C12 0.7(4) . . . . ?
C25 C22 C23 C12 -178.5(3) . . . . ?
N4 C12 C23 C22 0.3(5) . . . . ?
C2 C12 C23 C22 179.6(3) . . . . ?
N5 C15 C26 N6 0.2(4) . . . . ?
C16 C15 C26 N6 -178.2(3) . . . . ?
N5 C15 C26 N8 179.2(2) . . . . ?
C16 C15 C26 N8 0.8(4) . . . . ?
N7 C27 C28 C33 37.8(4) . . . . ?
C32 C27 C28 C33 -144.1(3) . . . . ?
N7 C27 C28 C29 158.2(3) . . . . ?
C32 C27 C28 C29 -23.7(4) . . . . ?
N7 C27 C28 C34 -80.9(3) . . . . ?
C32 C27 C28 C34 97.2(3) . . . . ?
C27 C28 C29 C30 51.7(3) . . . . ?
C33 C28 C29 C30 173.1(3) . . . . ?
C34 C28 C29 C30 -66.7(3) . . . . ?
C28 C29 C30 C31 -62.8(4) . . . . ?
C29 C30 C31 C36 161.6(3) . . . . ?
C29 C30 C31 C32 39.0(4) . . . . ?
C29 C30 C31 C35 -78.3(3) . . . . ?
N7 C27 C32 N8 -0.2(4) . . . . ?
C28 C27 C32 N8 -178.2(3) . . . . ?
N7 C27 C32 C31 -177.7(3) . . . . ?
C28 C27 C32 C31 4.2(4) . . . . ?
C36 C31 C32 N8 49.7(4) . . . . ?
C35 C31 C32 N8 -68.1(3) . . . . ?
C30 C31 C32 N8 171.3(3) . . . . ?
C36 C31 C32 C27 -132.7(3) . . . . ?
C35 C31 C32 C27 109.6(3) . . . . ?
C30 C31 C32 C27 -11.0(4) . . . . ?
C3 C1 N1 N2 -1.6(4) . . . . ?
C7 C1 N1 N2 173.7(3) . . . . ?
C1 N1 N2 C2 -0.1(4) . . . . ?
C1 N1 N2 Eu1 -169.3(2) . . . . ?
N3 C2 N2 N1 2.5(5) . . . . ?
C12 C2 N2 N1 -176.7(2) . . . . ?
N3 C2 N2 Eu1 171.5(2) . . . . ?
C12 C2 N2 Eu1 -7.6(4) . . . . ?
C1 C3 N3 C2 1.0(4) . . . . ?
C4 C3 N3 C2 -179.6(3) . . . . ?
N2 C2 N3 C3 -2.9(5) . . . . ?
C12 C2 N3 C3 176.3(3) . . . . ?
C23 C12 N4 C13 -0.3(4) . . . . ?
C2 C12 N4 C13 -179.7(2) . . . . ?
C23 C12 N4 Eu1 175.0(2) . . . . ?
C2 C12 N4 Eu1 -4.3(3) . . . . ?
C21 C13 N4 C12 -0.7(4) . . . . ?
C14 C13 N4 C12 178.7(2) . . . . ?
C21 C13 N4 Eu1 -176.1(2) . . . . ?
C14 C13 N4 Eu1 3.3(3) . . . . ?
C16 C15 N5 C14 -1.2(4) . . . . ?
C26 C15 N5 C14 -179.5(2) . . . . ?
C16 C15 N5 Eu1 -178.0(2) . . . . ?
C26 C15 N5 Eu1 3.7(3) . . . . ?
C18 C14 N5 C15 2.4(4) . . . . ?
C13 C14 N5 C15 -177.4(2) . . . . ?
C18 C14 N5 Eu1 179.3(2) . . . . ?
C13 C14 N5 Eu1 -0.6(3) . . . . ?
N8 C26 N6 N7 -0.4(4) . . . . ?
C15 C26 N6 N7 178.5(2) . . . . ?
N8 C26 N6 Eu1 177.2(2) . . . . ?
C15 C26 N6 Eu1 -3.9(3) . . . . ?
C32 C27 N7 N6 1.2(4) . . . . ?
C28 C27 N7 N6 179.4(2) . . . . ?
C26 N6 N7 C27 -1.0(4) . . . . ?
Eu1 N6 N7 C27 -178.55(19) . . . . ?
N6 C26 N8 C32 1.4(4) . . . . ?
C15 C26 N8 C32 -177.5(2) . . . . ?
C27 C32 N8 C26 -1.1(4) . . . . ?
C31 C32 N8 C26 176.7(2) . . . . ?
O3 N9 O1 Eu1 172.7(2) . . . . ?
O2 N9 O1 Eu1 -7.4(3) . . . . ?
O3 N9 O2 Eu1 -172.6(2) . . . . ?
O1 N9 O2 Eu1 7.5(3) . . . . ?
O6 N10 O4 Eu1 -177.2(2) . . . . ?
O5 N10 O4 Eu1 3.0(3) . . . . ?
O6 N10 O5 Eu1 177.3(3) . . . . ?
O4 N10 O5 Eu1 -2.9(3) . . . . ?
O9 N11 O7 Eu1 -171.6(3) . . . . ?
O8 N11 O7 Eu1 7.7(3) . . . . ?
O9 N11 O8 Eu1 171.5(3) . . . . ?
O7 N11 O8 Eu1 -7.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C16 H16 N12 0.95 2.68 3.569(5) 156.9 2_667
C23 H23 O3 0.95 2.57 3.409(4) 148.1 2_666
C37 H37B O3 0.98 2.48 3.337(4) 145.7 1_655

_refine_diff_density_max         1.039
_refine_diff_density_min         -0.854
_refine_diff_density_rms         0.089



####################################################################### 
# 
# 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_s4608ma
_database_code_depnum_ccdc_archive 'CCDC 1542304'
_audit_update_record             
;
2017-04-05 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------# 

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        4,7-Me-CyMe4-BTPhen
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H48 N8 O2'
_chemical_formula_weight         636.83

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

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                   16.9253(9)
_cell_length_b                   8.6647(5)
_cell_length_c                   23.1992(12)
_cell_angle_alpha                90
_cell_angle_beta                 98.832(4)
_cell_angle_gamma                90
_cell_volume                     3361.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2574
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      72.15

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_F_000             1368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.637
_shelx_estimated_absorpt_T_min   0.857
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.830644
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22281
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.022
_diffrn_reflns_theta_max         72.257
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6587
_reflns_number_gt                4903
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0909P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6587
_refine_ls_number_parameters     444
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1465
_refine_ls_wR_factor_gt          0.1312
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.00476(10) 0.22752(18) -0.01122(8) 0.0174(3) Uani 1 1 d . . . . .
C2 C 0.05454(10) 0.08752(19) -0.08087(8) 0.0181(3) Uani 1 1 d . . . . .
C3 C -0.02073(10) 0.0206(2) -0.10060(8) 0.0199(3) Uani 1 1 d . . . . .
H3 H -0.0265 -0.0513 -0.1319 0.024 Uiso 1 1 calc R U . . .
C4 C -0.08554(10) 0.05931(19) -0.07470(8) 0.0189(3) Uani 1 1 d . . . . .
C5 C -0.07371(10) 0.16976(19) -0.02905(8) 0.0179(3) Uani 1 1 d . . . . .
C6 C -0.13803(10) 0.2224(2) -0.00047(8) 0.0199(3) Uani 1 1 d . . . . .
H6 H -0.1906 0.1853 -0.0133 0.024 Uiso 1 1 calc R U . . .
C7 C -0.12567(10) 0.3233(2) 0.04413(8) 0.0199(3) Uani 1 1 d . . . . .
H7 H -0.1698 0.3569 0.0618 0.024 Uiso 1 1 calc R U . . .
C8 C -0.04721(10) 0.38119(19) 0.06555(8) 0.0184(3) Uani 1 1 d . . . . .
C9 C -0.03284(10) 0.4864(2) 0.11282(8) 0.0194(3) Uani 1 1 d . . . . .
C10 C 0.04422(10) 0.5351(2) 0.13018(8) 0.0194(3) Uani 1 1 d . . . . .
H10 H 0.0558 0.6092 0.1605 0.023 Uiso 1 1 calc R U . . .
C11 C 0.10587(10) 0.47475(19) 0.10289(8) 0.0177(3) Uani 1 1 d . . . . .
C12 C 0.01837(10) 0.33307(19) 0.03841(8) 0.0170(3) Uani 1 1 d . . . . .
C13 C 0.12411(10) 0.03411(19) -0.10857(8) 0.0190(3) Uani 1 1 d . . . . .
C14 C 0.24045(10) -0.0961(2) -0.15448(8) 0.0206(3) Uani 1 1 d . . . . .
C15 C 0.30419(11) -0.1846(2) -0.18011(8) 0.0239(4) Uani 1 1 d . . . . .
C16 C 0.38223(11) -0.0915(2) -0.16859(9) 0.0283(4) Uani 1 1 d . . . . .
H16A H 0.4259 -0.1522 -0.1815 0.034 Uiso 1 1 calc R U . . .
H16B H 0.3759 0.0049 -0.1918 0.034 Uiso 1 1 calc R U . . .
C17 C 0.40473(11) -0.0516(2) -0.10444(9) 0.0279(4) Uani 1 1 d . . . . .
H17A H 0.4575 0.0003 -0.0985 0.033 Uiso 1 1 calc R U . . .
H17B H 0.4100 -0.1482 -0.0814 0.033 Uiso 1 1 calc R U . . .
C18 C 0.34321(10) 0.0540(2) -0.08141(8) 0.0237(4) Uani 1 1 d . . . . .
C19 C 0.25845(10) 0.00815(19) -0.10717(8) 0.0188(3) Uani 1 1 d . . . . .
C20 C 0.31371(12) -0.3444(2) -0.15077(10) 0.0317(4) Uani 1 1 d . . . . .
H20A H 0.3236 -0.3316 -0.1083 0.048 Uiso 1 1 calc R U . . .
H20B H 0.3589 -0.3987 -0.1634 0.048 Uiso 1 1 calc R U . . .
H20C H 0.2647 -0.4044 -0.1620 0.048 Uiso 1 1 calc R U . . .
C21 C 0.27986(12) -0.2079(3) -0.24619(9) 0.0317(4) Uani 1 1 d . . . . .
H21A H 0.2288 -0.2631 -0.2536 0.048 Uiso 1 1 calc R U . . .
H21B H 0.3211 -0.2682 -0.2615 0.048 Uiso 1 1 calc R U . . .
H21C H 0.2742 -0.1071 -0.2656 0.048 Uiso 1 1 calc R U . . .
C22 C 0.35426(12) 0.0386(3) -0.01435(9) 0.0316(4) Uani 1 1 d . . . . .
H22A H 0.3184 0.1108 0.0013 0.047 Uiso 1 1 calc R U . . .
H22B H 0.4098 0.0625 0.0020 0.047 Uiso 1 1 calc R U . . .
H22C H 0.3417 -0.0671 -0.0039 0.047 Uiso 1 1 calc R U . . .
C23 C 0.35573(12) 0.2226(2) -0.09916(10) 0.0309(4) Uani 1 1 d . . . . .
H23A H 0.3510 0.2294 -0.1417 0.046 Uiso 1 1 calc R U . . .
H23B H 0.4091 0.2572 -0.0814 0.046 Uiso 1 1 calc R U . . .
H23C H 0.3151 0.2883 -0.0857 0.046 Uiso 1 1 calc R U . . .
C24 C -0.16505(10) -0.01908(19) -0.09187(8) 0.0217(4) Uani 1 1 d . . . . .
H24A H -0.1597 -0.1008 -0.1202 0.033 Uiso 1 1 calc R U . . .
H24B H -0.2046 0.0567 -0.1094 0.033 Uiso 1 1 calc R U . . .
H24C H -0.1826 -0.0641 -0.0572 0.033 Uiso 1 1 calc R U . . .
C25 C -0.09920(11) 0.5418(2) 0.14410(9) 0.0255(4) Uani 1 1 d . . . . .
H25A H -0.0782 0.6192 0.1733 0.038 Uiso 1 1 calc R U . . .
H25B H -0.1208 0.4544 0.1635 0.038 Uiso 1 1 calc R U . . .
H25C H -0.1417 0.5879 0.1159 0.038 Uiso 1 1 calc R U . . .
C26 C 0.19013(10) 0.5164(2) 0.12696(7) 0.0180(3) Uani 1 1 d . . . . .
C27 C 0.33426(10) 0.6008(2) 0.17336(7) 0.0189(3) Uani 1 1 d . . . . .
C28 C 0.41599(10) 0.6603(2) 0.20029(8) 0.0230(4) Uani 1 1 d . . . . .
C29 C 0.47772(11) 0.5285(2) 0.20405(9) 0.0283(4) Uani 1 1 d . . . . .
H29A H 0.4921 0.5101 0.1648 0.034 Uiso 1 1 calc R U . . .
H29B H 0.5268 0.5602 0.2302 0.034 Uiso 1 1 calc R U . . .
C30 C 0.44652(11) 0.3795(2) 0.22662(9) 0.0269(4) Uani 1 1 d . . . . .
H30A H 0.4307 0.3987 0.2654 0.032 Uiso 1 1 calc R U . . .
H30B H 0.4899 0.3019 0.2316 0.032 Uiso 1 1 calc R U . . .
C31 C 0.37424(10) 0.3141(2) 0.18529(8) 0.0216(4) Uani 1 1 d . . . . .
C32 C 0.31500(10) 0.4429(2) 0.16545(7) 0.0176(3) Uani 1 1 d . . . . .
C33 C 0.44193(12) 0.7923(2) 0.16321(11) 0.0342(5) Uani 1 1 d . . . . .
H33A H 0.4465 0.7535 0.1242 0.051 Uiso 1 1 calc R U . . .
H33B H 0.4938 0.8324 0.1817 0.051 Uiso 1 1 calc R U . . .
H33C H 0.4020 0.8750 0.1601 0.051 Uiso 1 1 calc R U . . .
C34 C 0.40831(12) 0.7234(2) 0.26124(9) 0.0296(4) Uani 1 1 d . . . . .
H34A H 0.3699 0.8088 0.2574 0.044 Uiso 1 1 calc R U . . .
H34B H 0.4605 0.7605 0.2803 0.044 Uiso 1 1 calc R U . . .
H34C H 0.3896 0.6411 0.2848 0.044 Uiso 1 1 calc R U . . .
C35 C 0.33276(12) 0.1913(2) 0.21777(9) 0.0291(4) Uani 1 1 d . . . . .
H35A H 0.3113 0.2396 0.2503 0.044 Uiso 1 1 calc R U . . .
H35B H 0.3715 0.1115 0.2329 0.044 Uiso 1 1 calc R U . . .
H35C H 0.2890 0.1444 0.1909 0.044 Uiso 1 1 calc R U . . .
C36 C 0.39865(12) 0.2408(2) 0.13036(9) 0.0274(4) Uani 1 1 d . . . . .
H36A H 0.3506 0.2100 0.1037 0.041 Uiso 1 1 calc R U . . .
H36B H 0.4319 0.1497 0.1414 0.041 Uiso 1 1 calc R U . . .
H36C H 0.4290 0.3158 0.1110 0.041 Uiso 1 1 calc R U . . .
C37 C 0.40221(15) 0.5690(3) 0.00876(12) 0.0452(6) Uani 1 1 d . . . . .
H37A H 0.4357 0.6615 0.0156 0.068 Uiso 1 1 calc R U . . .
H37B H 0.4125 0.5180 -0.0271 0.068 Uiso 1 1 calc R U . . .
H37C H 0.4150 0.4981 0.0418 0.068 Uiso 1 1 calc R U . . .
N1 N 0.06827(8) 0.18651(16) -0.03700(6) 0.0174(3) Uani 1 1 d . . . . .
N2 N 0.09459(8) 0.37846(16) 0.05809(6) 0.0168(3) Uani 1 1 d . . . . .
N3 N 0.10556(9) -0.05533(19) -0.15544(7) 0.0256(3) Uani 1 1 d . . . . .
N4 N 0.16501(10) -0.12119(19) -0.17845(7) 0.0256(3) Uani 1 1 d . . . . .
N5 N 0.19899(9) 0.07455(17) -0.08478(6) 0.0191(3) Uani 1 1 d . . . . .
N6 N 0.20430(9) 0.66637(17) 0.13631(7) 0.0216(3) Uani 1 1 d . . . . .
N7 N 0.27862(9) 0.70839(17) 0.15868(7) 0.0227(3) Uani 1 1 d . . . . .
N8 N 0.24259(9) 0.40129(16) 0.14040(7) 0.0191(3) Uani 1 1 d . . . . .
O1 O 0.32189(11) 0.6109(2) 0.00300(10) 0.0501(5) Uani 1 1 d . . . . .
H1 H 0.2937 0.5314 0.0037 0.075 Uiso 1 1 calc R U . . .
O2 O 0.22855(8) 0.34876(17) 0.99746(7) 0.0292(3) Uani 1 1 d . . . . .
H2A H 0.1850(19) 0.357(3) 1.0133(13) 0.043(7) Uiso 1 1 d . . . . .
H2B H 0.217(2) 0.282(4) 0.9721(16) 0.055(9) Uiso 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
C1 N1 1.355(2) . ?
C1 C5 1.420(2) . ?
C1 C12 1.461(2) . ?
C2 N1 1.324(2) . ?
C2 C3 1.411(2) . ?
C2 C13 1.499(2) . ?
C3 C4 1.371(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.419(2) . ?
C4 C24 1.505(2) . ?
C5 C6 1.433(2) . ?
C6 C7 1.346(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.435(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.418(3) . ?
C8 C12 1.420(2) . ?
C9 C10 1.371(2) . ?
C9 C25 1.506(2) . ?
C10 C11 1.402(2) . ?
C10 H10 0.9500 . ?
C11 N2 1.323(2) . ?
C11 C26 1.494(2) . ?
C12 N2 1.359(2) . ?
C13 N3 1.333(2) . ?
C13 N5 1.349(2) . ?
C14 N4 1.330(2) . ?
C14 C19 1.418(3) . ?
C14 C15 1.518(2) . ?
C15 C16 1.536(3) . ?
C15 C21 1.538(3) . ?
C15 C20 1.540(3) . ?
C16 C17 1.518(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.542(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.520(2) . ?
C18 C23 1.541(3) . ?
C18 C22 1.544(3) . ?
C19 N5 1.332(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 N6 1.333(2) . ?
C26 N8 1.340(2) . ?
C27 N7 1.331(2) . ?
C27 C32 1.412(2) . ?
C27 C28 1.518(2) . ?
C28 C33 1.535(3) . ?
C28 C34 1.540(3) . ?
C28 C29 1.541(3) . ?
C29 C30 1.518(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.542(2) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.523(2) . ?
C31 C35 1.535(3) . ?
C31 C36 1.536(3) . ?
C32 N8 1.323(2) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 O1 1.394(3) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
N3 N4 1.337(2) . ?
N6 N7 1.336(2) . ?
O1 H1 0.8400 . ?
O2 H2A 0.88(3) . ?
O2 H2B 0.83(4) . ?

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
N1 C1 C5 123.28(16) . . ?
N1 C1 C12 118.17(15) . . ?
C5 C1 C12 118.53(15) . . ?
N1 C2 C3 123.97(16) . . ?
N1 C2 C13 118.23(15) . . ?
C3 C2 C13 117.64(16) . . ?
C4 C3 C2 120.06(16) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 117.48(16) . . ?
C3 C4 C24 121.11(16) . . ?
C5 C4 C24 121.33(16) . . ?
C4 C5 C1 118.28(15) . . ?
C4 C5 C6 122.00(15) . . ?
C1 C5 C6 119.72(16) . . ?
C7 C6 C5 121.52(15) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C8 121.29(15) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C12 118.61(15) . . ?
C9 C8 C7 122.14(15) . . ?
C12 C8 C7 119.25(16) . . ?
C10 C9 C8 117.87(16) . . ?
C10 C9 C25 120.42(16) . . ?
C8 C9 C25 121.70(16) . . ?
C9 C10 C11 119.52(16) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
N2 C11 C10 124.20(15) . . ?
N2 C11 C26 117.40(14) . . ?
C10 C11 C26 118.36(15) . . ?
N2 C12 C8 122.16(16) . . ?
N2 C12 C1 118.22(15) . . ?
C8 C12 C1 119.59(15) . . ?
N3 C13 N5 125.02(16) . . ?
N3 C13 C2 115.29(15) . . ?
N5 C13 C2 119.67(15) . . ?
N4 C14 C19 120.41(16) . . ?
N4 C14 C15 116.63(16) . . ?
C19 C14 C15 122.96(16) . . ?
C14 C15 C16 108.08(15) . . ?
C14 C15 C21 111.04(16) . . ?
C16 C15 C21 109.50(16) . . ?
C14 C15 C20 108.26(15) . . ?
C16 C15 C20 111.50(17) . . ?
C21 C15 C20 108.47(17) . . ?
C17 C16 C15 111.70(16) . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 C18 113.19(16) . . ?
C16 C17 H17A 108.9 . . ?
C18 C17 H17A 108.9 . . ?
C16 C17 H17B 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.8 . . ?
C19 C18 C23 107.64(15) . . ?
C19 C18 C17 110.81(15) . . ?
C23 C18 C17 109.99(15) . . ?
C19 C18 C22 109.55(15) . . ?
C23 C18 C22 110.54(17) . . ?
C17 C18 C22 108.31(16) . . ?
N5 C19 C14 119.45(16) . . ?
N5 C19 C18 117.24(15) . . ?
C14 C19 C18 123.28(15) . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C21 H21A 109.5 . . ?
C15 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C15 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C4 C24 H24A 109.5 . . ?
C4 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C4 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C9 C25 H25A 109.5 . . ?
C9 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C9 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N6 C26 N8 126.26(16) . . ?
N6 C26 C11 115.70(15) . . ?
N8 C26 C11 117.90(15) . . ?
N7 C27 C32 120.33(16) . . ?
N7 C27 C28 115.58(16) . . ?
C32 C27 C28 124.06(16) . . ?
C27 C28 C33 110.07(16) . . ?
C27 C28 C34 107.37(15) . . ?
C33 C28 C34 108.78(16) . . ?
C27 C28 C29 109.80(15) . . ?
C33 C28 C29 109.49(16) . . ?
C34 C28 C29 111.29(16) . . ?
C30 C29 C28 112.39(16) . . ?
C30 C29 H29A 109.1 . . ?
C28 C29 H29A 109.1 . . ?
C30 C29 H29B 109.1 . . ?
C28 C29 H29B 109.1 . . ?
H29A C29 H29B 107.9 . . ?
C29 C30 C31 112.51(16) . . ?
C29 C30 H30A 109.1 . . ?
C31 C30 H30A 109.1 . . ?
C29 C30 H30B 109.1 . . ?
C31 C30 H30B 109.1 . . ?
H30A C30 H30B 107.8 . . ?
C32 C31 C35 109.07(15) . . ?
C32 C31 C36 107.50(15) . . ?
C35 C31 C36 108.78(16) . . ?
C32 C31 C30 109.95(15) . . ?
C35 C31 C30 109.18(16) . . ?
C36 C31 C30 112.29(15) . . ?
N8 C32 C27 120.06(15) . . ?
N8 C32 C31 117.08(15) . . ?
C27 C32 C31 122.85(15) . . ?
C28 C33 H33A 109.5 . . ?
C28 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C28 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C28 C34 H34A 109.5 . . ?
C28 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C28 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C31 C35 H35A 109.5 . . ?
C31 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C31 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C31 C36 H36A 109.5 . . ?
C31 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C31 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O1 C37 H37A 109.5 . . ?
O1 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O1 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C2 N1 C1 116.85(15) . . ?
C11 N2 C12 117.47(14) . . ?
C13 N3 N4 118.45(15) . . ?
C14 N4 N3 119.75(16) . . ?
C19 N5 C13 116.55(15) . . ?
C26 N6 N7 117.65(14) . . ?
C27 N7 N6 119.71(15) . . ?
C32 N8 C26 115.81(15) . . ?
C37 O1 H1 109.5 . . ?
H2A O2 H2B 103(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
N1 C2 C3 C4 1.2(3) . . . . ?
C13 C2 C3 C4 176.60(15) . . . . ?
C2 C3 C4 C5 1.3(2) . . . . ?
C2 C3 C4 C24 -175.39(16) . . . . ?
C3 C4 C5 C1 -3.0(2) . . . . ?
C24 C4 C5 C1 173.73(15) . . . . ?
C3 C4 C5 C6 177.73(16) . . . . ?
C24 C4 C5 C6 -5.6(3) . . . . ?
N1 C1 C5 C4 2.4(2) . . . . ?
C12 C1 C5 C4 -175.81(15) . . . . ?
N1 C1 C5 C6 -178.25(15) . . . . ?
C12 C1 C5 C6 3.5(2) . . . . ?
C4 C5 C6 C7 177.71(17) . . . . ?
C1 C5 C6 C7 -1.6(3) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C6 C7 C8 C9 -179.39(16) . . . . ?
C6 C7 C8 C12 1.2(3) . . . . ?
C12 C8 C9 C10 -0.6(2) . . . . ?
C7 C8 C9 C10 179.98(16) . . . . ?
C12 C8 C9 C25 -179.53(16) . . . . ?
C7 C8 C9 C25 1.0(3) . . . . ?
C8 C9 C10 C11 -2.9(2) . . . . ?
C25 C9 C10 C11 176.02(16) . . . . ?
C9 C10 C11 N2 4.3(3) . . . . ?
C9 C10 C11 C26 -173.33(16) . . . . ?
C9 C8 C12 N2 3.3(2) . . . . ?
C7 C8 C12 N2 -177.21(15) . . . . ?
C9 C8 C12 C1 -178.61(15) . . . . ?
C7 C8 C12 C1 0.8(2) . . . . ?
N1 C1 C12 N2 -3.3(2) . . . . ?
C5 C1 C12 N2 174.98(15) . . . . ?
N1 C1 C12 C8 178.52(14) . . . . ?
C5 C1 C12 C8 -3.2(2) . . . . ?
N1 C2 C13 N3 -174.73(15) . . . . ?
C3 C2 C13 N3 9.6(2) . . . . ?
N1 C2 C13 N5 6.8(2) . . . . ?
C3 C2 C13 N5 -168.83(16) . . . . ?
N4 C14 C15 C16 154.08(17) . . . . ?
C19 C14 C15 C16 -26.3(2) . . . . ?
N4 C14 C15 C21 34.0(2) . . . . ?
C19 C14 C15 C21 -146.39(17) . . . . ?
N4 C14 C15 C20 -85.0(2) . . . . ?
C19 C14 C15 C20 94.6(2) . . . . ?
C14 C15 C16 C17 53.3(2) . . . . ?
C21 C15 C16 C17 174.40(16) . . . . ?
C20 C15 C16 C17 -65.6(2) . . . . ?
C15 C16 C17 C18 -63.4(2) . . . . ?
C16 C17 C18 C19 39.4(2) . . . . ?
C16 C17 C18 C23 -79.5(2) . . . . ?
C16 C17 C18 C22 159.55(17) . . . . ?
N4 C14 C19 N5 3.6(3) . . . . ?
C15 C14 C19 N5 -175.98(16) . . . . ?
N4 C14 C19 C18 -174.01(17) . . . . ?
C15 C14 C19 C18 6.4(3) . . . . ?
C23 C18 C19 N5 -69.2(2) . . . . ?
C17 C18 C19 N5 170.47(16) . . . . ?
C22 C18 C19 N5 51.0(2) . . . . ?
C23 C18 C19 C14 108.49(19) . . . . ?
C17 C18 C19 C14 -11.8(2) . . . . ?
C22 C18 C19 C14 -131.27(18) . . . . ?
N2 C11 C26 N6 132.78(16) . . . . ?
C10 C11 C26 N6 -49.5(2) . . . . ?
N2 C11 C26 N8 -51.2(2) . . . . ?
C10 C11 C26 N8 126.52(17) . . . . ?
N7 C27 C28 C33 -48.6(2) . . . . ?
C32 C27 C28 C33 133.62(18) . . . . ?
N7 C27 C28 C34 69.7(2) . . . . ?
C32 C27 C28 C34 -108.12(19) . . . . ?
N7 C27 C28 C29 -169.16(16) . . . . ?
C32 C27 C28 C29 13.0(2) . . . . ?
C27 C28 C29 C30 -44.6(2) . . . . ?
C33 C28 C29 C30 -165.60(17) . . . . ?
C34 C28 C29 C30 74.1(2) . . . . ?
C28 C29 C30 C31 64.0(2) . . . . ?
C29 C30 C31 C32 -45.4(2) . . . . ?
C29 C30 C31 C35 -164.99(16) . . . . ?
C29 C30 C31 C36 74.3(2) . . . . ?
N7 C27 C32 N8 3.7(3) . . . . ?
C28 C27 C32 N8 -178.55(16) . . . . ?
N7 C27 C32 C31 -175.54(16) . . . . ?
C28 C27 C32 C31 2.2(3) . . . . ?
C35 C31 C32 N8 -46.0(2) . . . . ?
C36 C31 C32 N8 71.81(19) . . . . ?
C30 C31 C32 N8 -165.67(15) . . . . ?
C35 C31 C32 C27 133.31(17) . . . . ?
C36 C31 C32 C27 -108.89(19) . . . . ?
C30 C31 C32 C27 13.6(2) . . . . ?
C3 C2 N1 C1 -1.9(2) . . . . ?
C13 C2 N1 C1 -177.23(14) . . . . ?
C5 C1 N1 C2 0.0(2) . . . . ?
C12 C1 N1 C2 178.24(14) . . . . ?
C10 C11 N2 C12 -1.5(2) . . . . ?
C26 C11 N2 C12 176.07(15) . . . . ?
C8 C12 N2 C11 -2.3(2) . . . . ?
C1 C12 N2 C11 179.65(15) . . . . ?
N5 C13 N3 N4 5.7(3) . . . . ?
C2 C13 N3 N4 -172.63(16) . . . . ?
C19 C14 N4 N3 -4.3(3) . . . . ?
C15 C14 N4 N3 175.36(16) . . . . ?
C13 N3 N4 C14 -0.2(3) . . . . ?
C14 C19 N5 C13 1.4(2) . . . . ?
C18 C19 N5 C13 179.21(15) . . . . ?
N3 C13 N5 C19 -6.2(3) . . . . ?
C2 C13 N5 C19 172.05(15) . . . . ?
N8 C26 N6 N7 3.4(3) . . . . ?
C11 C26 N6 N7 178.98(15) . . . . ?
C32 C27 N7 N6 -0.1(3) . . . . ?
C28 C27 N7 N6 -177.99(15) . . . . ?
C26 N6 N7 C27 -3.2(3) . . . . ?
C27 C32 N8 C26 -3.6(2) . . . . ?
C31 C32 N8 C26 175.66(15) . . . . ?
N6 C26 N8 C32 0.2(3) . . . . ?
C11 C26 N8 C32 -175.33(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.84 1.92 2.759(2) 174.5 1_554
O2 H2B N1 0.83(4) 2.62(3) 3.0510(19) 114(3) 1_556
O2 H2A N2 0.88(3) 1.98(3) 2.857(2) 173(3) 1_556
O2 H2B N1 0.83(4) 2.62(3) 3.0510(19) 114(3) 1_556
O2 H2B N5 0.83(4) 2.22(4) 3.040(2) 169(3) 1_556

_refine_diff_density_max         0.331
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.051



