#------------------------------------------------------------------------------
#$Date: 2024-07-05 18:51:31 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292995 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/61/7716185.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7716185
loop_
_publ_author_name
'Parra-Cadenas, Blanca'
'Ginés, Carlos'
'García-Vivó, Daniel'
'Elorriaga, David'
'Carrillo-Hermosilla, Fernando'
_publ_section_title
;
 Zinc amidinate-catalysed cyclization reaction of carbodiimides and
 alkynes. An insight into the mechanism.
;
_journal_issue                   24
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10050
_journal_page_last               10054
_journal_paper_doi               10.1039/d4dt01265h
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C43 H50 N2 O2, C6 H6'
_chemical_formula_sum            'C49 H56 N2 O2'
_chemical_formula_weight         704.95
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-04-09 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                102.253(3)
_cell_angle_beta                 97.132(3)
_cell_angle_gamma                103.187(3)
_cell_formula_units_Z            2
_cell_length_a                   9.426(2)
_cell_length_b                   10.912(2)
_cell_length_c                   21.672(5)
_cell_measurement_reflns_used    2072
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.49
_cell_measurement_theta_min      2.26
_cell_volume                     2085.7(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14371
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.344
_diffrn_reflns_theta_min         2.411
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0625 before and 0.0390 after correction.
The Ratio of minimum to maximum transmission is 0.8906.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     519
_refine_ls_number_reflns         7460
_refine_ls_number_restraints     198
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1216
_refine_ls_R_factor_gt           0.0588
_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)+(0.0828P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1779
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3883
_reflns_number_total             7460
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt01265h2.cif
_cod_data_source_block           bp14_0m
_cod_depositor_comments
'Adding full bibliography for 7716182--7716185.cif.'
_cod_database_code               7716185
_shelx_shelxl_version_number     2017/1
_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.
;
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Restrained distances
 C44-C44A \\sim C45-C45A \\sim C46-C46A \\sim C47-C47A \\sim C48-C48A \\sim
C49-C49A
 with sigma of 0.01
2. Uiso/Uaniso restraints and constraints
C44 \\sim C44A \\sim C45 \\sim C45A \\sim C46 \\sim C46A \\sim C47 \\sim C47A
\\sim C48 \\sim C48A \\sim C49 \\sim C49A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
3. Others
 Sof(C47A)=Sof(H47A)=Sof(C48A)=Sof(H48A)=Sof(C49A)=Sof(H49A)=Sof(C44A)=
 Sof(H44A)=Sof(C45A)=Sof(H45A)=Sof(C46A)=Sof(H46A)=1-FVAR(1)
 Sof(C44)=Sof(H44)=Sof(C45)=Sof(H45)=Sof(C46)=Sof(H46)=Sof(C47)=Sof(H47)=
 Sof(C48)=Sof(H48)=Sof(C49)=Sof(H49)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C19(H19), C22(H22)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17), C26(H26), C28(H28),
 C31(H31), C32(H32), C34(H34), C35(H35), C38(H38), C39(H39), C41(H41), C42(H42),
  C44(H44), C45(H45), C46(H46), C47(H47), C48(H48), C49(H49), C47A(H47A),
 C48A(H48A), C49A(H49A), C44A(H44A), C45A(H45A), C46A(H46A)
4.c Fitted hexagon refined as free rotating group:
 C44(C45,C46,C47,C48,C49), C47A(C48A,C49A,C44A,C45A,C46A)
4.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C),
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C36(H36A,H36B,H36C), C43(H43A,H43B,H43C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.0686(3) 0.0352(2) 0.92621(11) 0.1015(7) Uani 1 1 d . . . . .
O2 O 0.5178(2) 0.2766(2) 0.46057(9) 0.0886(7) Uani 1 1 d . . . . .
N1 N 0.2220(2) 0.53774(18) 0.80345(8) 0.0435(5) Uani 1 1 d . . . . .
N2 N 0.1994(2) 0.72583(18) 0.77502(8) 0.0460(5) Uani 1 1 d . . . . .
C1 C 0.1807(3) 0.5881(2) 0.86432(10) 0.0460(6) Uani 1 1 d . . . . .
C2 C 0.2937(3) 0.6641(2) 0.91497(11) 0.0535(6) Uani 1 1 d . . . . .
C3 C 0.2542(3) 0.7019(3) 0.97452(12) 0.0666(8) Uani 1 1 d . . . . .
H3 H 0.326512 0.753762 1.009142 0.080 Uiso 1 1 calc R U . . .
C4 C 0.1113(4) 0.6643(3) 0.98294(13) 0.0723(8) Uani 1 1 d . . . . .
H4 H 0.088137 0.687701 1.023540 0.087 Uiso 1 1 calc R U . . .
C5 C 0.0011(3) 0.5922(3) 0.93214(12) 0.0650(7) Uani 1 1 d . . . . .
H5 H -0.096181 0.569214 0.938511 0.078 Uiso 1 1 calc R U . . .
C6 C 0.0334(3) 0.5533(2) 0.87127(11) 0.0513(6) Uani 1 1 d . . . . .
C7 C 0.4546(3) 0.7024(3) 0.90730(12) 0.0661(7) Uani 1 1 d . . . . .
H7 H 0.455549 0.703041 0.862203 0.079 Uiso 1 1 calc R U . . .
C8 C 0.5360(3) 0.6034(3) 0.92239(15) 0.0932(10) Uani 1 1 d . . . . .
H8A H 0.524897 0.591575 0.964335 0.140 Uiso 1 1 calc R U . . .
H8B H 0.639270 0.634423 0.921258 0.140 Uiso 1 1 calc R U . . .
H8C H 0.495088 0.522029 0.891050 0.140 Uiso 1 1 calc R U . . .
C9 C 0.5377(4) 0.8386(3) 0.94813(15) 0.0983(11) Uani 1 1 d . . . . .
H9A H 0.480809 0.898842 0.941641 0.147 Uiso 1 1 calc R U . . .
H9B H 0.632114 0.864655 0.935716 0.147 Uiso 1 1 calc R U . . .
H9C H 0.552371 0.837576 0.992636 0.147 Uiso 1 1 calc R U . . .
C10 C -0.0911(3) 0.4774(3) 0.81594(12) 0.0681(8) Uani 1 1 d . . . . .
H10 H -0.046494 0.450502 0.778526 0.082 Uiso 1 1 calc R U . . .
C11 C -0.1830(4) 0.3548(3) 0.82959(16) 0.0989(11) Uani 1 1 d . . . . .
H11A H -0.118944 0.303046 0.840934 0.148 Uiso 1 1 calc R U . . .
H11B H -0.254706 0.305713 0.791965 0.148 Uiso 1 1 calc R U . . .
H11C H -0.232992 0.378625 0.864444 0.148 Uiso 1 1 calc R U . . .
C12 C -0.1886(4) 0.5644(4) 0.79912(15) 0.0951(10) Uani 1 1 d . . . . .
H12A H -0.237424 0.589024 0.834290 0.143 Uiso 1 1 calc R U . . .
H12B H -0.261404 0.517871 0.761439 0.143 Uiso 1 1 calc R U . . .
H12C H -0.128134 0.640926 0.791076 0.143 Uiso 1 1 calc R U . . .
C13 C 0.2113(3) 0.8088(2) 0.73262(11) 0.0489(6) Uani 1 1 d . . . . .
C14 C 0.0960(3) 0.7897(2) 0.68097(11) 0.0550(7) Uani 1 1 d . . . . .
C15 C 0.1061(3) 0.8808(3) 0.64449(12) 0.0672(8) Uani 1 1 d . . . . .
H15 H 0.029242 0.869657 0.610761 0.081 Uiso 1 1 calc R U . . .
C16 C 0.2256(4) 0.9863(3) 0.65665(14) 0.0739(9) Uani 1 1 d . . . . .
H16 H 0.230469 1.045043 0.631061 0.089 Uiso 1 1 calc R U . . .
C17 C 0.3387(3) 1.0046(3) 0.70714(13) 0.0682(8) Uani 1 1 d . . . . .
H17 H 0.420267 1.076039 0.715354 0.082 Uiso 1 1 calc R U . . .
C18 C 0.3330(3) 0.9182(2) 0.74605(11) 0.0551(6) Uani 1 1 d . . . . .
C19 C -0.0380(3) 0.6737(3) 0.66357(13) 0.0695(8) Uani 1 1 d . . . . .
H19 H -0.028074 0.622626 0.695213 0.083 Uiso 1 1 calc R U . . .
C20 C -0.0468(4) 0.5856(3) 0.59731(15) 0.0951(10) Uani 1 1 d . . . . .
H20A H -0.054112 0.633772 0.565314 0.143 Uiso 1 1 calc R U . . .
H20B H -0.132485 0.512982 0.588315 0.143 Uiso 1 1 calc R U . . .
H20C H 0.040719 0.554701 0.596744 0.143 Uiso 1 1 calc R U . . .
C21 C -0.1817(3) 0.7153(4) 0.66707(15) 0.0928(10) Uani 1 1 d . . . . .
H21A H -0.175751 0.768885 0.709121 0.139 Uiso 1 1 calc R U . . .
H21B H -0.263566 0.639649 0.658669 0.139 Uiso 1 1 calc R U . . .
H21C H -0.195893 0.763580 0.635618 0.139 Uiso 1 1 calc R U . . .
C22 C 0.4572(3) 0.9425(3) 0.80183(13) 0.0712(8) Uani 1 1 d . . . . .
H22 H 0.420716 0.885959 0.829188 0.085 Uiso 1 1 calc R U . . .
C23 C 0.5892(4) 0.9025(5) 0.77940(19) 0.1359(16) Uani 1 1 d . . . . .
H23A H 0.560029 0.811887 0.757632 0.204 Uiso 1 1 calc R U . . .
H23B H 0.665936 0.917422 0.815772 0.204 Uiso 1 1 calc R U . . .
H23C H 0.625399 0.952746 0.750538 0.204 Uiso 1 1 calc R U . . .
C24 C 0.4998(4) 1.0806(3) 0.84304(17) 0.1134(12) Uani 1 1 d . . . . .
H24A H 0.535885 1.139519 0.817889 0.170 Uiso 1 1 calc R U . . .
H24B H 0.575892 1.089370 0.878737 0.170 Uiso 1 1 calc R U . . .
H24C H 0.414568 1.100370 0.858629 0.170 Uiso 1 1 calc R U . . .
C25 C 0.2381(2) 0.6186(2) 0.76031(10) 0.0432(6) Uani 1 1 d . . . . .
C26 C 0.2972(3) 0.5714(2) 0.70485(10) 0.0482(6) Uani 1 1 d . . . . .
H26 H 0.314933 0.623587 0.676362 0.058 Uiso 1 1 calc R U . . .
C27 C 0.3283(3) 0.4545(2) 0.69196(10) 0.0472(6) Uani 1 1 d . . . . .
C28 C 0.3001(3) 0.3756(2) 0.73563(11) 0.0533(6) Uani 1 1 d . . . . .
H28 H 0.320529 0.294884 0.727208 0.064 Uiso 1 1 calc R U . . .
C29 C 0.2444(3) 0.4134(2) 0.78921(10) 0.0474(6) Uani 1 1 d . . . . .
C30 C 0.3832(3) 0.4070(2) 0.63278(11) 0.0495(6) Uani 1 1 d . . . . .
C31 C 0.3326(3) 0.4332(3) 0.57543(11) 0.0584(7) Uani 1 1 d . . . . .
H31 H 0.264649 0.482988 0.574922 0.070 Uiso 1 1 calc R U . . .
C32 C 0.3783(3) 0.3888(3) 0.51991(12) 0.0637(7) Uani 1 1 d . . . . .
H32 H 0.341717 0.408263 0.482311 0.076 Uiso 1 1 calc R U . . .
C33 C 0.4786(3) 0.3153(3) 0.51939(12) 0.0619(7) Uani 1 1 d . . . . .
C34 C 0.5315(3) 0.2862(3) 0.57462(13) 0.0689(8) Uani 1 1 d . . . . .
H34 H 0.600371 0.237195 0.574645 0.083 Uiso 1 1 calc R U . . .
C35 C 0.4814(3) 0.3306(3) 0.63093(12) 0.0627(7) Uani 1 1 d . . . . .
H35 H 0.515065 0.308249 0.668107 0.075 Uiso 1 1 calc R U . . .
C36 C 0.6299(4) 0.2124(4) 0.45720(17) 0.1178(14) Uani 1 1 d . . . . .
H36A H 0.648917 0.195092 0.414127 0.177 Uiso 1 1 calc R U . . .
H36B H 0.599348 0.131903 0.469175 0.177 Uiso 1 1 calc R U . . .
H36C H 0.718457 0.266024 0.485989 0.177 Uiso 1 1 calc R U . . .
C37 C 0.1955(3) 0.3194(2) 0.82744(11) 0.0508(6) Uani 1 1 d . . . . .
C38 C 0.1234(3) 0.1919(3) 0.79349(13) 0.0620(7) Uani 1 1 d . . . . .
H38 H 0.104722 0.171939 0.748858 0.074 Uiso 1 1 calc R U . . .
C39 C 0.0787(3) 0.0938(3) 0.82416(15) 0.0708(8) Uani 1 1 d . . . . .
H39 H 0.031261 0.009597 0.800300 0.085 Uiso 1 1 calc R U . . .
C40 C 0.1053(3) 0.1225(3) 0.89023(15) 0.0696(8) Uani 1 1 d . . . . .
C41 C 0.1742(3) 0.2470(3) 0.92451(13) 0.0666(8) Uani 1 1 d . . . . .
H41 H 0.191107 0.266357 0.969134 0.080 Uiso 1 1 calc R U . . .
C42 C 0.2188(3) 0.3437(3) 0.89444(12) 0.0590(7) Uani 1 1 d . . . . .
H42 H 0.265533 0.427449 0.919071 0.071 Uiso 1 1 calc R U . . .
C43 C 0.0088(5) -0.0961(4) 0.89415(19) 0.1196(13) Uani 1 1 d . . . . .
H43A H -0.080575 -0.105429 0.864949 0.179 Uiso 1 1 calc R U . . .
H43B H -0.013090 -0.146096 0.924894 0.179 Uiso 1 1 calc R U . . .
H43C H 0.079068 -0.126601 0.870644 0.179 Uiso 1 1 calc R U . . .
C44 C 0.8134(10) 0.1474(11) 0.6591(2) 0.1067(19) Uani 0.626(6) 1 d G U P A 1
H44 H 0.787485 0.163866 0.699519 0.128 Uiso 0.626(6) 1 calc R U P A 1
C45 C 0.7462(5) 0.0294(8) 0.6149(5) 0.0986(18) Uani 0.626(6) 1 d G U P A 1
H45 H 0.675286 -0.033113 0.625671 0.118 Uiso 0.626(6) 1 calc R U P A 1
C46 C 0.7850(9) 0.0047(4) 0.5545(4) 0.0990(18) Uani 0.626(6) 1 d G U P A 1
H46 H 0.739987 -0.074230 0.524899 0.119 Uiso 0.626(6) 1 calc R U P A 1
C47 C 0.8910(10) 0.0981(9) 0.5384(2) 0.1041(18) Uani 0.626(6) 1 d G U P A 1
H47 H 0.916888 0.081630 0.497976 0.125 Uiso 0.626(6) 1 calc R U P A 1
C48 C 0.9582(5) 0.2161(7) 0.5826(5) 0.1021(18) Uani 0.626(6) 1 d G U P A 1
H48 H 1.029089 0.278609 0.571824 0.123 Uiso 0.626(6) 1 calc R U P A 1
C49 C 0.9194(9) 0.2408(5) 0.6430(4) 0.105(2) Uani 0.626(6) 1 d G U P A 1
H49 H 0.964390 0.319729 0.672596 0.126 Uiso 0.626(6) 1 calc R U P A 1
C47A C 0.9495(13) 0.1533(18) 0.5535(6) 0.107(3) Uani 0.374(6) 1 d G U P A 2
H47A H 1.008828 0.176323 0.524420 0.129 Uiso 0.374(6) 1 calc R U P A 2
C48A C 0.9639(11) 0.2393(8) 0.6127(8) 0.100(3) Uani 0.374(6) 1 d G U P A 2
H48A H 1.032839 0.319859 0.623205 0.120 Uiso 0.374(6) 1 calc R U P A 2
C49A C 0.8753(17) 0.2048(13) 0.6563(3) 0.099(2) Uani 0.374(6) 1 d G U P A 2
H49A H 0.884886 0.262373 0.695851 0.119 Uiso 0.374(6) 1 calc R U P A 2
C44A C 0.7722(13) 0.0844(16) 0.6406(7) 0.101(2) Uani 0.374(6) 1 d G U P A 2
H44A H 0.712919 0.061352 0.669713 0.122 Uiso 0.374(6) 1 calc R U P A 2
C45A C 0.7578(11) -0.0016(6) 0.5814(9) 0.096(2) Uani 0.374(6) 1 d G U P A 2
H45A H 0.688906 -0.082186 0.570928 0.115 Uiso 0.374(6) 1 calc R U P A 2
C46A C 0.8465(17) 0.0328(14) 0.5379(4) 0.108(3) Uani 0.374(6) 1 d G U P A 2
H46A H 0.836858 -0.024702 0.498281 0.129 Uiso 0.374(6) 1 calc R U P A 2
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'
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
C40 O1 C43 118.2(3) . . ?
C33 O2 C36 118.4(2) . . ?
C25 N1 C1 117.72(17) . . ?
C29 N1 C1 120.06(17) . . ?
C29 N1 C25 122.23(17) . . ?
C25 N2 C13 119.13(18) . . ?
C2 C1 N1 117.8(2) . . ?
C6 C1 N1 119.5(2) . . ?
C6 C1 C2 122.5(2) . . ?
C1 C2 C7 122.5(2) . . ?
C3 C2 C1 117.2(2) . . ?
C3 C2 C7 120.3(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.7(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 117.5(2) . . ?
C1 C6 C10 123.0(2) . . ?
C5 C6 C10 119.5(2) . . ?
C2 C7 H7 107.5 . . ?
C2 C7 C8 111.4(2) . . ?
C2 C7 C9 112.7(2) . . ?
C8 C7 H7 107.5 . . ?
C8 C7 C9 110.0(3) . . ?
C9 C7 H7 107.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10 107.7 . . ?
C6 C10 C11 112.2(2) . . ?
C6 C10 C12 110.2(2) . . ?
C11 C10 H10 107.7 . . ?
C11 C10 C12 111.2(3) . . ?
C12 C10 H10 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N2 120.6(2) . . ?
C18 C13 N2 119.4(2) . . ?
C18 C13 C14 119.6(2) . . ?
C13 C14 C19 122.4(2) . . ?
C15 C14 C13 118.6(3) . . ?
C15 C14 C19 119.0(2) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 C14 122.0(3) . . ?
C16 C15 H15 119.0 . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.3(3) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.1(3) . . ?
C18 C17 H17 119.4 . . ?
C13 C18 C22 120.9(2) . . ?
C17 C18 C13 119.3(3) . . ?
C17 C18 C22 119.8(3) . . ?
C14 C19 H19 107.6 . . ?
C14 C19 C20 112.1(2) . . ?
C14 C19 C21 111.6(2) . . ?
C20 C19 H19 107.6 . . ?
C21 C19 H19 107.6 . . ?
C21 C19 C20 110.2(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 H22 106.8 . . ?
C18 C22 C23 111.0(2) . . ?
C18 C22 C24 113.1(3) . . ?
C23 C22 H22 106.8 . . ?
C23 C22 C24 112.0(3) . . ?
C24 C22 H22 106.8 . . ?
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 . . ?
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 . . ?
N1 C25 C26 115.4(2) . . ?
N2 C25 N1 117.23(18) . . ?
N2 C25 C26 127.3(2) . . ?
C25 C26 H26 118.4 . . ?
C27 C26 C25 123.1(2) . . ?
C27 C26 H26 118.4 . . ?
C26 C27 C28 117.9(2) . . ?
C26 C27 C30 121.4(2) . . ?
C28 C27 C30 120.6(2) . . ?
C27 C28 H28 118.7 . . ?
C29 C28 C27 122.5(2) . . ?
C29 C28 H28 118.7 . . ?
N1 C29 C37 121.43(18) . . ?
C28 C29 N1 118.4(2) . . ?
C28 C29 C37 119.9(2) . . ?
C31 C30 C27 121.0(2) . . ?
C35 C30 C27 122.3(2) . . ?
C35 C30 C31 116.7(2) . . ?
C30 C31 H31 118.7 . . ?
C32 C31 C30 122.5(2) . . ?
C32 C31 H31 118.7 . . ?
C31 C32 H32 120.1 . . ?
C31 C32 C33 119.9(2) . . ?
C33 C32 H32 120.1 . . ?
C32 C33 O2 114.8(2) . . ?
C34 C33 O2 125.3(2) . . ?
C34 C33 C32 120.0(2) . . ?
C33 C34 H34 120.3 . . ?
C33 C34 C35 119.4(2) . . ?
C35 C34 H34 120.3 . . ?
C30 C35 C34 121.5(2) . . ?
C30 C35 H35 119.2 . . ?
C34 C35 H35 119.2 . . ?
O2 C36 H36A 109.5 . . ?
O2 C36 H36B 109.5 . . ?
O2 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C38 C37 C29 117.0(2) . . ?
C38 C37 C42 116.2(2) . . ?
C42 C37 C29 126.7(2) . . ?
C37 C38 H38 118.9 . . ?
C39 C38 C37 122.2(3) . . ?
C39 C38 H38 118.9 . . ?
C38 C39 H39 120.3 . . ?
C40 C39 C38 119.3(3) . . ?
C40 C39 H39 120.3 . . ?
O1 C40 C39 125.2(3) . . ?
O1 C40 C41 115.3(3) . . ?
C41 C40 C39 119.5(3) . . ?
C40 C41 H41 119.4 . . ?
C40 C41 C42 121.3(3) . . ?
C42 C41 H41 119.4 . . ?
C37 C42 H42 119.3 . . ?
C41 C42 C37 121.4(3) . . ?
C41 C42 H42 119.3 . . ?
O1 C43 H43A 109.5 . . ?
O1 C43 H43B 109.5 . . ?
O1 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C45 C44 H44 120.0 . . ?
C45 C44 C49 120.0 . . ?
C49 C44 H44 120.0 . . ?
C44 C45 H45 120.0 . . ?
C46 C45 C44 120.0 . . ?
C46 C45 H45 120.0 . . ?
C45 C46 H46 120.0 . . ?
C47 C46 C45 120.0 . . ?
C47 C46 H46 120.0 . . ?
C46 C47 H47 120.0 . . ?
C48 C47 C46 120.0 . . ?
C48 C47 H47 120.0 . . ?
C47 C48 H48 120.0 . . ?
C49 C48 C47 120.0 . . ?
C49 C48 H48 120.0 . . ?
C44 C49 H49 120.0 . . ?
C48 C49 C44 120.0 . . ?
C48 C49 H49 120.0 . . ?
C48A C47A H47A 120.0 . . ?
C48A C47A C46A 120.0 . . ?
C46A C47A H47A 120.0 . . ?
C47A C48A H48A 120.0 . . ?
C47A C48A C49A 120.0 . . ?
C49A C48A H48A 120.0 . . ?
C48A C49A H49A 120.0 . . ?
C44A C49A C48A 120.0 . . ?
C44A C49A H49A 120.0 . . ?
C49A C44A H44A 120.0 . . ?
C49A C44A C45A 120.0 . . ?
C45A C44A H44A 120.0 . . ?
C44A C45A H45A 120.0 . . ?
C46A C45A C44A 120.0 . . ?
C46A C45A H45A 120.0 . . ?
C47A C46A H46A 120.0 . . ?
C45A C46A C47A 120.0 . . ?
C45A C46A H46A 120.0 . . ?
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 C40 1.367(3) . ?
O1 C43 1.401(4) . ?
O2 C33 1.378(3) . ?
O2 C36 1.396(4) . ?
N1 C1 1.453(3) . ?
N1 C25 1.414(3) . ?
N1 C29 1.396(3) . ?
N2 C13 1.417(3) . ?
N2 C25 1.292(3) . ?
C1 C2 1.396(3) . ?
C1 C6 1.390(3) . ?
C2 C3 1.392(3) . ?
C2 C7 1.518(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.362(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(3) . ?
C6 C10 1.512(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.526(4) . ?
C7 C9 1.530(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9800 . ?
C10 C11 1.527(4) . ?
C10 C12 1.530(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.405(3) . ?
C13 C18 1.404(3) . ?
C14 C15 1.389(4) . ?
C14 C19 1.513(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.367(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.376(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(4) . ?
C18 C22 1.508(4) . ?
C19 H19 0.9800 . ?
C19 C20 1.530(4) . ?
C19 C21 1.529(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22 0.9800 . ?
C22 C23 1.511(4) . ?
C22 C24 1.514(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.433(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.353(3) . ?
C27 C28 1.418(3) . ?
C27 C30 1.478(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.357(3) . ?
C29 C37 1.480(3) . ?
C30 C31 1.385(3) . ?
C30 C35 1.379(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.358(3) . ?
C32 H32 0.9300 . ?
C32 C33 1.372(3) . ?
C33 C34 1.367(4) . ?
C34 H34 0.9300 . ?
C34 C35 1.394(3) . ?
C35 H35 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 C38 1.396(3) . ?
C37 C42 1.399(3) . ?
C38 H38 0.9300 . ?
C38 C39 1.390(4) . ?
C39 H39 0.9300 . ?
C39 C40 1.377(4) . ?
C40 C41 1.367(4) . ?
C41 H41 0.9300 . ?
C41 C42 1.368(4) . ?
C42 H42 0.9300 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 H44 0.9300 . ?
C44 C45 1.3900 . ?
C44 C49 1.3900 . ?
C45 H45 0.9300 . ?
C45 C46 1.3900 . ?
C46 H46 0.9300 . ?
C46 C47 1.3900 . ?
C47 H47 0.9300 . ?
C47 C48 1.3900 . ?
C48 H48 0.9300 . ?
C48 C49 1.3900 . ?
C49 H49 0.9300 . ?
C47A H47A 0.9300 . ?
C47A C48A 1.3900 . ?
C47A C46A 1.3900 . ?
C48A H48A 0.9300 . ?
C48A C49A 1.3900 . ?
C49A H49A 0.9300 . ?
C49A C44A 1.3900 . ?
C44A H44A 0.9300 . ?
C44A C45A 1.3900 . ?
C45A H45A 0.9300 . ?
C45A C46A 1.3900 . ?
C46A H46A 0.9300 . ?
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
O1 C40 C41 C42 179.0(2) . . . . ?
O2 C33 C34 C35 -179.4(2) . . . . ?
N1 C1 C2 C3 -174.3(2) . . . . ?
N1 C1 C2 C7 4.1(3) . . . . ?
N1 C1 C6 C5 173.3(2) . . . . ?
N1 C1 C6 C10 -7.5(4) . . . . ?
N1 C25 C26 C27 3.6(3) . . . . ?
N1 C29 C37 C38 135.5(2) . . . . ?
N1 C29 C37 C42 -47.0(3) . . . . ?
N2 C13 C14 C15 173.8(2) . . . . ?
N2 C13 C14 C19 -6.5(3) . . . . ?
N2 C13 C18 C17 -175.15(19) . . . . ?
N2 C13 C18 C22 5.0(3) . . . . ?
N2 C25 C26 C27 -176.9(2) . . . . ?
C1 N1 C25 N2 -7.3(3) . . . . ?
C1 N1 C25 C26 172.33(19) . . . . ?
C1 N1 C29 C28 -172.2(2) . . . . ?
C1 N1 C29 C37 13.8(3) . . . . ?
C1 C2 C3 C4 1.0(4) . . . . ?
C1 C2 C7 C8 -90.9(3) . . . . ?
C1 C2 C7 C9 144.9(3) . . . . ?
C1 C6 C10 C11 125.4(3) . . . . ?
C1 C6 C10 C12 -110.1(3) . . . . ?
C2 C1 C6 C5 -2.7(4) . . . . ?
C2 C1 C6 C10 176.5(2) . . . . ?
C2 C3 C4 C5 -2.7(4) . . . . ?
C3 C2 C7 C8 87.5(3) . . . . ?
C3 C2 C7 C9 -36.7(3) . . . . ?
C3 C4 C5 C6 1.6(4) . . . . ?
C4 C5 C6 C1 1.1(4) . . . . ?
C4 C5 C6 C10 -178.2(3) . . . . ?
C5 C6 C10 C11 -55.4(3) . . . . ?
C5 C6 C10 C12 69.0(3) . . . . ?
C6 C1 C2 C3 1.7(4) . . . . ?
C6 C1 C2 C7 -179.8(2) . . . . ?
C7 C2 C3 C4 -177.4(3) . . . . ?
C13 N2 C25 N1 -178.94(19) . . . . ?
C13 N2 C25 C26 1.5(4) . . . . ?
C13 C14 C15 C16 1.3(4) . . . . ?
C13 C14 C19 C20 -115.5(3) . . . . ?
C13 C14 C19 C21 120.3(3) . . . . ?
C13 C18 C22 C23 101.0(3) . . . . ?
C13 C18 C22 C24 -132.1(3) . . . . ?
C14 C13 C18 C17 -1.2(3) . . . . ?
C14 C13 C18 C22 179.0(2) . . . . ?
C14 C15 C16 C17 -1.1(4) . . . . ?
C15 C14 C19 C20 64.2(3) . . . . ?
C15 C14 C19 C21 -60.0(3) . . . . ?
C15 C16 C17 C18 -0.3(4) . . . . ?
C16 C17 C18 C13 1.5(4) . . . . ?
C16 C17 C18 C22 -178.7(2) . . . . ?
C17 C18 C22 C23 -78.8(3) . . . . ?
C17 C18 C22 C24 48.1(4) . . . . ?
C18 C13 C14 C15 -0.1(3) . . . . ?
C18 C13 C14 C19 179.7(2) . . . . ?
C19 C14 C15 C16 -178.5(2) . . . . ?
C25 N1 C1 C2 -85.8(3) . . . . ?
C25 N1 C1 C6 98.0(3) . . . . ?
C25 N1 C29 C28 7.9(3) . . . . ?
C25 N1 C29 C37 -166.1(2) . . . . ?
C25 N2 C13 C14 85.9(3) . . . . ?
C25 N2 C13 C18 -100.2(3) . . . . ?
C25 C26 C27 C28 0.3(4) . . . . ?
C25 C26 C27 C30 177.4(2) . . . . ?
C26 C27 C28 C29 -0.3(4) . . . . ?
C26 C27 C30 C31 -36.1(4) . . . . ?
C26 C27 C30 C35 146.7(3) . . . . ?
C27 C28 C29 N1 -3.6(4) . . . . ?
C27 C28 C29 C37 170.5(2) . . . . ?
C27 C30 C31 C32 -178.6(2) . . . . ?
C27 C30 C35 C34 179.7(2) . . . . ?
C28 C27 C30 C31 140.9(3) . . . . ?
C28 C27 C30 C35 -36.3(4) . . . . ?
C28 C29 C37 C38 -38.4(3) . . . . ?
C28 C29 C37 C42 139.0(3) . . . . ?
C29 N1 C1 C2 94.3(3) . . . . ?
C29 N1 C1 C6 -81.9(3) . . . . ?
C29 N1 C25 N2 172.7(2) . . . . ?
C29 N1 C25 C26 -7.7(3) . . . . ?
C29 C37 C38 C39 176.9(2) . . . . ?
C29 C37 C42 C41 -176.9(2) . . . . ?
C30 C27 C28 C29 -177.4(2) . . . . ?
C30 C31 C32 C33 -0.1(4) . . . . ?
C31 C30 C35 C34 2.4(4) . . . . ?
C31 C32 C33 O2 -179.5(2) . . . . ?
C31 C32 C33 C34 0.4(4) . . . . ?
C32 C33 C34 C35 0.7(4) . . . . ?
C33 C34 C35 C30 -2.2(4) . . . . ?
C35 C30 C31 C32 -1.3(4) . . . . ?
C36 O2 C33 C32 173.8(3) . . . . ?
C36 O2 C33 C34 -6.0(4) . . . . ?
C37 C38 C39 C40 0.3(4) . . . . ?
C38 C37 C42 C41 0.6(4) . . . . ?
C38 C39 C40 O1 -179.2(3) . . . . ?
C38 C39 C40 C41 0.5(4) . . . . ?
C39 C40 C41 C42 -0.7(4) . . . . ?
C40 C41 C42 C37 0.1(4) . . . . ?
C42 C37 C38 C39 -0.8(4) . . . . ?
C43 O1 C40 C39 4.8(4) . . . . ?
C43 O1 C40 C41 -174.9(3) . . . . ?
C44 C45 C46 C47 0.0 . . . . ?
C45 C44 C49 C48 0.0 . . . . ?
C45 C46 C47 C48 0.0 . . . . ?
C46 C47 C48 C49 0.0 . . . . ?
C47 C48 C49 C44 0.0 . . . . ?
C49 C44 C45 C46 0.0 . . . . ?
C47A C48A C49A C44A 0.0 . . . . ?
C48A C47A C46A C45A 0.0 . . . . ?
C48A C49A C44A C45A 0.0 . . . . ?
C49A C44A C45A C46A 0.0 . . . . ?
C44A C45A C46A C47A 0.0 . . . . ?
C46A C47A C48A C49A 0.0 . . . . ?
