#------------------------------------------------------------------------------
#$Date: 2024-10-06 08:13:43 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295104 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/35/7133521.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_7133521
loop_
_publ_author_name
'Kaulage, Sandeep H.'
'Parvin, Nasrina'
'Khopade, Kishor V.'
'Khan, Shabana'
_publ_section_title
;
 A hybrid silylene-Pd catalyst: efficient C-N cross-coupling of sterically
 bulky amines and chiral amines.
;
_journal_issue                   73
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9958
_journal_page_last               9961
_journal_paper_doi               10.1039/d4cc03108c
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H21 N'
_chemical_formula_sum            'C28 H21 N'
_chemical_formula_weight         371.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-08-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-08-08 deposited with the CCDC.	2024-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.6857(15)
_cell_length_b                   12.012(2)
_cell_length_c                   37.160(6)
_cell_measurement_reflns_used    8988
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      74.62
_cell_measurement_theta_min      3.57
_cell_volume                     3877.0(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1220
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            64151
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.833
_diffrn_reflns_theta_min         2.378
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.558
_exptl_absorpt_correction_T_max  0.7266
_exptl_absorpt_correction_T_min  0.6387
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1772 before and 0.1065 after correction.
The Ratio of minimum to maximum transmission is 0.8790.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       Plates
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.268
_exptl_crystal_size_min          0.186
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 2100 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(4)
_refine_ls_extinction_coef       0.00057(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     526
_refine_ls_number_reflns         7843
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0737
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0040P)²+4.0502P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1351
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                6422
_reflns_number_total             7843
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc03108c2.cif
_cod_data_source_block           5c
_cod_depositor_comments
'Adding full bibliography for 7133516--7133523.cif.'
_cod_original_cell_volume        3877.1(11)
_cod_database_code               7133521
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C1(H1), C29(H29)
1.b Aromatic/amide H refined with riding coordinates:
 N1(H1A), N2(H2), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
  C14(H14), C15(H15), C19(H19), C20(H20), C23(H23), C24(H24), C26(H26),
 C27(H27), C28(H28), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39),
  C40(H40), C42(H42), C43(H43), C47(H47), C48(H48), C51(H51), C52(H52),
 C53(H53), C55(H55), C56(H56)
1.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C30(H30A,H30B,H30C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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 0.3997(5) 0.4665(4) 0.26094(12) 0.0298(10) Uani 1 1 d . . . . .
H1 H 0.465412 0.432950 0.241671 0.036 Uiso 1 1 calc R U . . .
N1 N 0.2449(5) 0.4820(3) 0.24663(10) 0.0338(9) Uani 1 1 d . . . . .
H1A H 0.199870 0.546641 0.250249 0.041 Uiso 1 1 calc R U . . .
N2 N 0.8584(5) 0.6074(3) 0.53373(11) 0.0357(10) Uani 1 1 d . . . . .
H2 H 0.893903 0.673267 0.539953 0.043 Uiso 1 1 calc R U . . .
C2 C 0.4638(6) 0.5810(4) 0.27017(14) 0.0403(12) Uani 1 1 d . . . . .
H2A H 0.568459 0.573155 0.279666 0.061 Uiso 1 1 calc R U . . .
H2B H 0.398111 0.616262 0.288333 0.061 Uiso 1 1 calc R U . . .
H2C H 0.465909 0.627213 0.248445 0.061 Uiso 1 1 calc R U . . .
C3 C 0.4029(5) 0.3900(4) 0.29351(12) 0.0292(10) Uani 1 1 d . . . . .
C4 C 0.2715(5) 0.3699(4) 0.31272(12) 0.0333(11) Uani 1 1 d . . . . .
H4 H 0.177580 0.402977 0.305154 0.040 Uiso 1 1 calc R U . . .
C5 C 0.2721(6) 0.3012(4) 0.34345(13) 0.0384(12) Uani 1 1 d . . . . .
H5 H 0.179118 0.287631 0.356170 0.046 Uiso 1 1 calc R U . . .
C7 C 0.5455(5) 0.2726(4) 0.33625(12) 0.0306(10) Uani 1 1 d . . . . .
C6 C 0.4063(6) 0.2544(4) 0.35491(13) 0.0358(11) Uani 1 1 d . . . . .
H6 H 0.406080 0.208714 0.375776 0.043 Uiso 1 1 calc R U . . .
C8 C 0.5443(5) 0.3396(4) 0.30446(12) 0.0296(10) Uani 1 1 d . . . . .
C9 C 0.6857(6) 0.3501(4) 0.28556(13) 0.0367(12) Uani 1 1 d . . . . .
H9 H 0.688804 0.394692 0.264452 0.044 Uiso 1 1 calc R U . . .
C10 C 0.8174(6) 0.2985(5) 0.29666(14) 0.0427(13) Uani 1 1 d . . . . .
H10 H 0.909374 0.306481 0.283063 0.051 Uiso 1 1 calc R U . . .
C11 C 0.8176(6) 0.2334(5) 0.32818(14) 0.0434(13) Uani 1 1 d . . . . .
H11 H 0.909637 0.198420 0.336127 0.052 Uiso 1 1 calc R U . . .
C12 C 0.6842(6) 0.2210(5) 0.34720(13) 0.0402(13) Uani 1 1 d . . . . .
H12 H 0.684517 0.176572 0.368346 0.048 Uiso 1 1 calc R U . . .
C13 C 0.1646(5) 0.4023(4) 0.22786(12) 0.0281(10) Uani 1 1 d . . . . .
C14 C 0.2298(6) 0.2980(4) 0.22114(12) 0.0335(11) Uani 1 1 d . . . . .
H14 H 0.329360 0.281615 0.230326 0.040 Uiso 1 1 calc R U . . .
C15 C 0.1526(6) 0.2186(4) 0.20147(13) 0.0351(11) Uani 1 1 d . . . . .
H15 H 0.200589 0.148826 0.197134 0.042 Uiso 1 1 calc R U . . .
C16 C 0.0053(6) 0.2382(4) 0.18771(12) 0.0321(11) Uani 1 1 d . . . . .
C17 C -0.0644(5) 0.3419(4) 0.19505(11) 0.0287(10) Uani 1 1 d . . . . .
C19 C -0.0627(5) 0.5279(4) 0.22153(12) 0.0302(10) Uani 1 1 d . . . . .
H19 H -0.011432 0.584189 0.234901 0.036 Uiso 1 1 calc R U . . .
C18 C 0.0141(5) 0.4246(4) 0.21502(11) 0.0271(10) Uani 1 1 d . . . . .
C20 C -0.2074(6) 0.5474(4) 0.20904(12) 0.0334(11) Uani 1 1 d . . . . .
H20 H -0.254612 0.617244 0.213817 0.040 Uiso 1 1 calc R U . . .
C21 C -0.2903(5) 0.4656(4) 0.18891(12) 0.0330(11) Uani 1 1 d . . . . .
C22 C -0.2164(5) 0.3634(4) 0.18187(11) 0.0288(10) Uani 1 1 d . . . . .
C23 C -0.0768(6) 0.1576(4) 0.16666(13) 0.0405(13) Uani 1 1 d . . . . .
H23 H -0.029843 0.087871 0.161671 0.049 Uiso 1 1 calc R U . . .
C24 C -0.2176(7) 0.1782(5) 0.15393(14) 0.0455(14) Uani 1 1 d . . . . .
H24 H -0.267856 0.123303 0.139779 0.055 Uiso 1 1 calc R U . . .
C25 C -0.2942(6) 0.2808(4) 0.16107(12) 0.0361(12) Uani 1 1 d . . . . .
C26 C -0.4433(6) 0.3034(5) 0.14874(14) 0.0431(13) Uani 1 1 d . . . . .
H26 H -0.495926 0.248813 0.134913 0.052 Uiso 1 1 calc R U . . .
C27 C -0.5154(6) 0.4029(5) 0.15622(14) 0.0456(14) Uani 1 1 d . . . . .
H27 H -0.616882 0.416055 0.147695 0.055 Uiso 1 1 calc R U . . .
C28 C -0.4402(6) 0.4837(5) 0.17612(13) 0.0418(13) Uani 1 1 d . . . . .
H28 H -0.490585 0.552112 0.181163 0.050 Uiso 1 1 calc R U . . .
C29 C 0.7047(6) 0.6018(4) 0.51810(12) 0.0330(11) Uani 1 1 d . . . . .
H29 H 0.643553 0.544513 0.531420 0.040 Uiso 1 1 calc R U . . .
C30 C 0.6308(6) 0.7158(4) 0.52404(13) 0.0380(12) Uani 1 1 d . . . . .
H30A H 0.689120 0.772483 0.510857 0.057 Uiso 1 1 calc R U . . .
H30B H 0.631518 0.733558 0.549780 0.057 Uiso 1 1 calc R U . . .
H30C H 0.524372 0.714435 0.515295 0.057 Uiso 1 1 calc R U . . .
C31 C 0.7048(6) 0.5725(4) 0.47859(12) 0.0307(10) Uani 1 1 d . . . . .
C32 C 0.5632(6) 0.5389(4) 0.46158(12) 0.0308(11) Uani 1 1 d . . . . .
C33 C 0.5622(6) 0.5173(4) 0.42403(13) 0.0338(11) Uani 1 1 d . . . . .
C34 C 0.7020(6) 0.5283(4) 0.40410(14) 0.0408(13) Uani 1 1 d . . . . .
H34 H 0.701621 0.515444 0.378881 0.049 Uiso 1 1 calc R U . . .
C35 C 0.8351(6) 0.5569(4) 0.42066(13) 0.0386(12) Uani 1 1 d . . . . .
H35 H 0.928230 0.561687 0.407326 0.046 Uiso 1 1 calc R U . . .
C36 C 0.8342(6) 0.5794(4) 0.45790(13) 0.0347(11) Uani 1 1 d . . . . .
H36 H 0.928139 0.600360 0.469114 0.042 Uiso 1 1 calc R U . . .
C37 C 0.4236(6) 0.5219(4) 0.48088(13) 0.0347(11) Uani 1 1 d . . . . .
H37 H 0.421409 0.534936 0.506088 0.042 Uiso 1 1 calc R U . . .
C38 C 0.2920(6) 0.4870(5) 0.46377(14) 0.0418(13) Uani 1 1 d . . . . .
H38 H 0.200016 0.476075 0.477133 0.050 Uiso 1 1 calc R U . . .
C39 C 0.2936(6) 0.4677(5) 0.42677(15) 0.0456(13) Uani 1 1 d . . . . .
H39 H 0.202235 0.444046 0.414979 0.055 Uiso 1 1 calc R U . . .
C40 C 0.4256(7) 0.4827(4) 0.40735(13) 0.0410(13) Uani 1 1 d . . . . .
H40 H 0.424798 0.469399 0.382153 0.049 Uiso 1 1 calc R U . . .
C41 C 0.9522(5) 0.5158(4) 0.53944(12) 0.0274(10) Uani 1 1 d . . . . .
C42 C 0.9056(6) 0.4088(4) 0.52876(13) 0.0334(11) Uani 1 1 d . . . . .
H42 H 0.806181 0.398580 0.518643 0.040 Uiso 1 1 calc R U . . .
C43 C 1.0018(6) 0.3184(4) 0.53274(13) 0.0342(11) Uani 1 1 d . . . . .
H43 H 0.966570 0.246998 0.525491 0.041 Uiso 1 1 calc R U . . .
C45 C 1.1972(5) 0.4360(4) 0.55931(11) 0.0268(10) Uani 1 1 d . . . . .
C46 C 1.0984(5) 0.5303(4) 0.55559(11) 0.0269(10) Uani 1 1 d . . . . .
C47 C 1.1539(6) 0.6350(4) 0.56814(12) 0.0309(11) Uani 1 1 d . . . . .
H47 H 1.091541 0.699366 0.565276 0.037 Uiso 1 1 calc R U . . .
C48 C 1.2935(6) 0.6449(4) 0.58407(12) 0.0314(11) Uani 1 1 d . . . . .
H48 H 1.324221 0.715590 0.592983 0.038 Uiso 1 1 calc R U . . .
C49 C 1.3956(5) 0.5532(4) 0.58791(11) 0.0285(10) Uani 1 1 d . . . . .
C50 C 1.3465(5) 0.4483(4) 0.57463(11) 0.0273(10) Uani 1 1 d . . . . .
C51 C 1.5412(6) 0.5629(5) 0.60314(12) 0.0370(12) Uani 1 1 d . . . . .
H51 H 1.571976 0.631846 0.613369 0.044 Uiso 1 1 calc R U . . .
C52 C 1.6415(6) 0.4740(5) 0.60366(13) 0.0423(13) Uani 1 1 d . . . . .
H52 H 1.741694 0.482630 0.613533 0.051 Uiso 1 1 calc R U . . .
C53 C 1.5963(6) 0.3718(5) 0.58976(13) 0.0385(12) Uani 1 1 d . . . . .
H53 H 1.667070 0.311567 0.589639 0.046 Uiso 1 1 calc R U . . .
C54 C 1.4494(6) 0.3564(4) 0.57604(12) 0.0315(11) Uani 1 1 d . . . . .
C55 C 1.3981(6) 0.2511(4) 0.56261(13) 0.0386(12) Uani 1 1 d . . . . .
H55 H 1.466508 0.189373 0.562671 0.046 Uiso 1 1 calc R U . . .
C56 C 1.2541(6) 0.2384(4) 0.54990(13) 0.0346(11) Uani 1 1 d . . . . .
H56 H 1.221385 0.166449 0.542541 0.042 Uiso 1 1 calc R U . . .
C57 C 1.1490(5) 0.3289(4) 0.54708(12) 0.0300(10) Uani 1 1 d . . . . .
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'
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 H1 108.5 . . ?
N1 C1 C2 107.7(4) . . ?
N1 C1 C3 112.6(4) . . ?
C2 C1 H1 108.5 . . ?
C3 C1 H1 108.5 . . ?
C3 C1 C2 111.1(4) . . ?
C1 N1 H1A 117.8 . . ?
C13 N1 C1 124.3(4) . . ?
C13 N1 H1A 117.8 . . ?
C29 N2 H2 117.9 . . ?
C41 N2 H2 117.9 . . ?
C41 N2 C29 124.2(4) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 C1 120.5(4) . . ?
C4 C3 C8 119.6(4) . . ?
C8 C3 C1 119.9(4) . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.6(5) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.9(5) . . ?
C6 C5 H5 120.1 . . ?
C6 C7 C8 119.1(4) . . ?
C6 C7 C12 121.4(4) . . ?
C12 C7 C8 119.4(4) . . ?
C5 C6 C7 121.0(5) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C3 C8 C7 118.7(4) . . ?
C9 C8 C3 124.4(4) . . ?
C9 C8 C7 116.9(4) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 C8 122.3(5) . . ?
C10 C9 H9 118.8 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.3(5) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.3(5) . . ?
C12 C11 H11 120.3 . . ?
C7 C12 H12 119.1 . . ?
C11 C12 C7 121.7(5) . . ?
C11 C12 H12 119.1 . . ?
N1 C13 C14 120.6(4) . . ?
N1 C13 C18 120.5(4) . . ?
C14 C13 C18 118.9(4) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.2(5) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 119.2 . . ?
C14 C15 C16 121.6(5) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C17 118.1(4) . . ?
C15 C16 C23 122.7(5) . . ?
C17 C16 C23 119.2(5) . . ?
C16 C17 C18 120.9(4) . . ?
C16 C17 C22 119.3(4) . . ?
C18 C17 C22 119.8(4) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C20 C19 C18 121.6(5) . . ?
C13 C18 C19 122.5(4) . . ?
C17 C18 C13 119.2(4) . . ?
C17 C18 C19 118.2(4) . . ?
C19 C20 H20 119.2 . . ?
C19 C20 C21 121.7(5) . . ?
C21 C20 H20 119.2 . . ?
C22 C21 C20 117.8(4) . . ?
C28 C21 C20 122.5(5) . . ?
C28 C21 C22 119.6(5) . . ?
C21 C22 C17 120.9(4) . . ?
C21 C22 C25 119.4(4) . . ?
C25 C22 C17 119.7(5) . . ?
C16 C23 H23 119.2 . . ?
C24 C23 C16 121.6(5) . . ?
C24 C23 H23 119.2 . . ?
C23 C24 H24 119.3 . . ?
C23 C24 C25 121.5(5) . . ?
C25 C24 H24 119.3 . . ?
C24 C25 C22 118.7(5) . . ?
C26 C25 C22 118.7(5) . . ?
C26 C25 C24 122.6(5) . . ?
C25 C26 H26 119.2 . . ?
C27 C26 C25 121.5(5) . . ?
C27 C26 H26 119.2 . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.1(5) . . ?
C28 C27 H27 119.9 . . ?
C21 C28 H28 119.7 . . ?
C27 C28 C21 120.7(6) . . ?
C27 C28 H28 119.7 . . ?
N2 C29 H29 108.7 . . ?
N2 C29 C30 106.6(4) . . ?
N2 C29 C31 113.5(4) . . ?
C30 C29 H29 108.7 . . ?
C31 C29 H29 108.7 . . ?
C31 C29 C30 110.4(4) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 C31 C29 119.5(4) . . ?
C36 C31 C29 122.3(5) . . ?
C36 C31 C32 118.2(4) . . ?
C33 C32 C31 119.2(4) . . ?
C33 C32 C37 117.6(5) . . ?
C37 C32 C31 123.1(4) . . ?
C32 C33 C34 119.2(5) . . ?
C40 C33 C32 119.6(5) . . ?
C40 C33 C34 121.2(4) . . ?
C33 C34 H34 119.5 . . ?
C35 C34 C33 120.9(5) . . ?
C35 C34 H34 119.5 . . ?
C34 C35 H35 120.3 . . ?
C34 C35 C36 119.3(5) . . ?
C36 C35 H35 120.3 . . ?
C31 C36 C35 123.1(5) . . ?
C31 C36 H36 118.5 . . ?
C35 C36 H36 118.5 . . ?
C32 C37 H37 119.3 . . ?
C38 C37 C32 121.3(5) . . ?
C38 C37 H37 119.3 . . ?
C37 C38 H38 120.0 . . ?
C37 C38 C39 119.9(5) . . ?
C39 C38 H38 120.0 . . ?
C38 C39 H39 119.8 . . ?
C40 C39 C38 120.5(5) . . ?
C40 C39 H39 119.8 . . ?
C33 C40 H40 119.5 . . ?
C39 C40 C33 121.0(5) . . ?
C39 C40 H40 119.5 . . ?
N2 C41 C42 120.9(4) . . ?
N2 C41 C46 119.6(4) . . ?
C42 C41 C46 119.4(4) . . ?
C41 C42 H42 119.5 . . ?
C43 C42 C41 121.1(4) . . ?
C43 C42 H42 119.5 . . ?
C42 C43 H43 119.1 . . ?
C42 C43 C57 121.8(4) . . ?
C57 C43 H43 119.1 . . ?
C50 C45 C46 120.2(4) . . ?
C50 C45 C57 119.2(4) . . ?
C57 C45 C46 120.6(4) . . ?
C41 C46 C45 118.8(4) . . ?
C41 C46 C47 123.5(4) . . ?
C47 C46 C45 117.7(4) . . ?
C46 C47 H47 119.2 . . ?
C48 C47 C46 121.5(5) . . ?
C48 C47 H47 119.2 . . ?
C47 C48 H48 118.8 . . ?
C47 C48 C49 122.3(4) . . ?
C49 C48 H48 118.8 . . ?
C50 C49 C48 117.8(4) . . ?
C51 C49 C48 123.0(4) . . ?
C51 C49 C50 119.3(4) . . ?
C49 C50 C45 120.3(4) . . ?
C49 C50 C54 119.2(4) . . ?
C54 C50 C45 120.4(4) . . ?
C49 C51 H51 119.5 . . ?
C52 C51 C49 121.1(5) . . ?
C52 C51 H51 119.5 . . ?
C51 C52 H52 120.0 . . ?
C51 C52 C53 120.0(5) . . ?
C53 C52 H52 120.0 . . ?
C52 C53 H53 119.5 . . ?
C54 C53 C52 121.1(5) . . ?
C54 C53 H53 119.5 . . ?
C50 C54 C55 118.6(4) . . ?
C53 C54 C50 119.2(5) . . ?
C53 C54 C55 122.2(5) . . ?
C54 C55 H55 119.6 . . ?
C56 C55 C54 120.8(5) . . ?
C56 C55 H55 119.6 . . ?
C55 C56 H56 118.8 . . ?
C55 C56 C57 122.4(5) . . ?
C57 C56 H56 118.8 . . ?
C43 C57 C45 118.2(4) . . ?
C43 C57 C56 123.3(5) . . ?
C56 C57 C45 118.5(4) . . ?
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 H1 1.0000 . ?
C1 N1 1.458(6) . ?
C1 C2 1.523(7) . ?
C1 C3 1.520(6) . ?
N1 H1A 0.8800 . ?
N1 C13 1.374(6) . ?
N2 H2 0.8800 . ?
N2 C29 1.457(6) . ?
N2 C41 1.386(6) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.367(6) . ?
C3 C8 1.428(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.409(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.362(7) . ?
C7 C6 1.411(7) . ?
C7 C8 1.429(6) . ?
C7 C12 1.414(7) . ?
C6 H6 0.9500 . ?
C8 C9 1.421(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.365(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.408(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.365(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.397(6) . ?
C13 C18 1.417(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.376(7) . ?
C15 H15 0.9500 . ?
C15 C16 1.398(7) . ?
C16 C17 1.412(7) . ?
C16 C23 1.435(7) . ?
C17 C18 1.415(6) . ?
C17 C22 1.431(6) . ?
C19 H19 0.9500 . ?
C19 C18 1.429(6) . ?
C19 C20 1.361(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.430(7) . ?
C21 C22 1.410(7) . ?
C21 C28 1.403(7) . ?
C22 C25 1.428(6) . ?
C23 H23 0.9500 . ?
C23 C24 1.334(8) . ?
C24 H24 0.9500 . ?
C24 C25 1.425(8) . ?
C25 C26 1.400(7) . ?
C26 H26 0.9500 . ?
C26 C27 1.378(8) . ?
C27 H27 0.9500 . ?
C27 C28 1.384(8) . ?
C28 H28 0.9500 . ?
C29 H29 1.0000 . ?
C29 C30 1.529(7) . ?
C29 C31 1.510(6) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.440(7) . ?
C31 C36 1.365(7) . ?
C32 C33 1.419(6) . ?
C32 C37 1.424(7) . ?
C33 C34 1.429(7) . ?
C33 C40 1.401(7) . ?
C34 H34 0.9500 . ?
C34 C35 1.354(8) . ?
C35 H35 0.9500 . ?
C35 C36 1.410(7) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C37 C38 1.373(7) . ?
C38 H38 0.9500 . ?
C38 C39 1.394(7) . ?
C39 H39 0.9500 . ?
C39 C40 1.367(8) . ?
C40 H40 0.9500 . ?
C41 C42 1.405(6) . ?
C41 C46 1.415(6) . ?
C42 H42 0.9500 . ?
C42 C43 1.378(7) . ?
C43 H43 0.9500 . ?
C43 C57 1.391(7) . ?
C45 C46 1.428(6) . ?
C45 C50 1.424(6) . ?
C45 C57 1.427(6) . ?
C46 C47 1.425(6) . ?
C47 H47 0.9500 . ?
C47 C48 1.354(7) . ?
C48 H48 0.9500 . ?
C48 C49 1.421(7) . ?
C49 C50 1.419(6) . ?
C49 C51 1.390(7) . ?
C50 C54 1.421(7) . ?
C51 H51 0.9500 . ?
C51 C52 1.379(7) . ?
C52 H52 0.9500 . ?
C52 C53 1.388(8) . ?
C53 H53 0.9500 . ?
C53 C54 1.386(7) . ?
C54 C55 1.431(7) . ?
C55 H55 0.9500 . ?
C55 C56 1.346(7) . ?
C56 H56 0.9500 . ?
C56 C57 1.423(6) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C13 C14 -0.2(7) . . . . ?
C1 N1 C13 C18 179.8(4) . . . . ?
C1 C3 C4 C5 -178.6(4) . . . . ?
C1 C3 C8 C7 176.8(4) . . . . ?
C1 C3 C8 C9 -4.0(7) . . . . ?
N1 C1 C3 C4 -19.1(6) . . . . ?
N1 C1 C3 C8 161.6(4) . . . . ?
N1 C13 C14 C15 -178.0(4) . . . . ?
N1 C13 C18 C17 178.5(4) . . . . ?
N1 C13 C18 C19 -1.7(7) . . . . ?
N2 C29 C31 C32 165.7(4) . . . . ?
N2 C29 C31 C36 -16.0(7) . . . . ?
N2 C41 C42 C43 176.7(4) . . . . ?
N2 C41 C46 C45 -176.3(4) . . . . ?
N2 C41 C46 C47 3.0(7) . . . . ?
C2 C1 N1 C13 164.3(4) . . . . ?
C2 C1 C3 C4 101.8(5) . . . . ?
C2 C1 C3 C8 -77.5(5) . . . . ?
C3 C1 N1 C13 -72.9(6) . . . . ?
C3 C4 C5 C6 0.9(7) . . . . ?
C3 C8 C9 C10 -178.6(5) . . . . ?
C4 C3 C8 C7 -2.4(7) . . . . ?
C4 C3 C8 C9 176.7(5) . . . . ?
C4 C5 C6 C7 -0.6(8) . . . . ?
C7 C8 C9 C10 0.6(7) . . . . ?
C6 C7 C8 C3 2.7(7) . . . . ?
C6 C7 C8 C9 -176.5(5) . . . . ?
C6 C7 C12 C11 176.4(5) . . . . ?
C8 C3 C4 C5 0.6(7) . . . . ?
C8 C7 C6 C5 -1.3(7) . . . . ?
C8 C7 C12 C11 0.0(8) . . . . ?
C8 C9 C10 C11 -1.1(8) . . . . ?
C9 C10 C11 C12 1.0(9) . . . . ?
C10 C11 C12 C7 -0.5(9) . . . . ?
C12 C7 C6 C5 -177.6(5) . . . . ?
C12 C7 C8 C3 179.2(5) . . . . ?
C12 C7 C8 C9 0.0(7) . . . . ?
C13 C14 C15 C16 -0.7(7) . . . . ?
C14 C13 C18 C17 -1.5(6) . . . . ?
C14 C13 C18 C19 178.3(4) . . . . ?
C14 C15 C16 C17 -1.0(7) . . . . ?
C14 C15 C16 C23 179.0(5) . . . . ?
C15 C16 C17 C18 1.5(7) . . . . ?
C15 C16 C17 C22 -178.8(4) . . . . ?
C15 C16 C23 C24 179.8(5) . . . . ?
C16 C17 C18 C13 -0.2(6) . . . . ?
C16 C17 C18 C19 180.0(4) . . . . ?
C16 C17 C22 C21 179.5(4) . . . . ?
C16 C17 C22 C25 -1.0(6) . . . . ?
C16 C23 C24 C25 -0.9(8) . . . . ?
C17 C16 C23 C24 -0.1(7) . . . . ?
C17 C22 C25 C24 0.0(6) . . . . ?
C17 C22 C25 C26 179.5(4) . . . . ?
C19 C20 C21 C22 -0.8(7) . . . . ?
C19 C20 C21 C28 179.3(4) . . . . ?
C18 C13 C14 C15 2.0(7) . . . . ?
C18 C17 C22 C21 -0.8(6) . . . . ?
C18 C17 C22 C25 178.6(4) . . . . ?
C18 C19 C20 C21 0.3(7) . . . . ?
C20 C19 C18 C13 -179.8(4) . . . . ?
C20 C19 C18 C17 0.0(6) . . . . ?
C20 C21 C22 C17 1.1(6) . . . . ?
C20 C21 C22 C25 -178.4(4) . . . . ?
C20 C21 C28 C27 178.9(5) . . . . ?
C21 C22 C25 C24 179.5(4) . . . . ?
C21 C22 C25 C26 -1.1(6) . . . . ?
C22 C17 C18 C13 -179.9(4) . . . . ?
C22 C17 C18 C19 0.3(6) . . . . ?
C22 C21 C28 C27 -1.0(7) . . . . ?
C22 C25 C26 C27 0.1(7) . . . . ?
C23 C16 C17 C18 -178.6(4) . . . . ?
C23 C16 C17 C22 1.1(6) . . . . ?
C23 C24 C25 C22 1.0(7) . . . . ?
C23 C24 C25 C26 -178.4(5) . . . . ?
C24 C25 C26 C27 179.5(5) . . . . ?
C25 C26 C27 C28 0.4(8) . . . . ?
C26 C27 C28 C21 0.0(8) . . . . ?
C28 C21 C22 C17 -179.0(4) . . . . ?
C28 C21 C22 C25 1.5(6) . . . . ?
C29 N2 C41 C42 2.7(7) . . . . ?
C29 N2 C41 C46 -178.6(4) . . . . ?
C29 C31 C32 C33 176.6(4) . . . . ?
C29 C31 C32 C37 -5.8(7) . . . . ?
C29 C31 C36 C35 -177.3(4) . . . . ?
C30 C29 C31 C32 -74.7(6) . . . . ?
C30 C29 C31 C36 103.6(5) . . . . ?
C31 C32 C33 C34 0.7(7) . . . . ?
C31 C32 C33 C40 178.9(4) . . . . ?
C31 C32 C37 C38 -178.3(5) . . . . ?
C32 C31 C36 C35 1.0(7) . . . . ?
C32 C33 C34 C35 1.2(8) . . . . ?
C32 C33 C40 C39 -0.9(8) . . . . ?
C32 C37 C38 C39 -0.1(8) . . . . ?
C33 C32 C37 C38 -0.7(7) . . . . ?
C33 C34 C35 C36 -2.0(8) . . . . ?
C34 C33 C40 C39 177.2(5) . . . . ?
C34 C35 C36 C31 0.9(8) . . . . ?
C36 C31 C32 C33 -1.8(7) . . . . ?
C36 C31 C32 C37 175.8(5) . . . . ?
C37 C32 C33 C34 -177.0(5) . . . . ?
C37 C32 C33 C40 1.1(7) . . . . ?
C37 C38 C39 C40 0.4(9) . . . . ?
C38 C39 C40 C33 0.2(9) . . . . ?
C40 C33 C34 C35 -176.9(5) . . . . ?
C41 N2 C29 C30 168.3(4) . . . . ?
C41 N2 C29 C31 -69.9(6) . . . . ?
C41 C42 C43 C57 -0.6(8) . . . . ?
C41 C46 C47 C48 178.7(4) . . . . ?
C42 C41 C46 C45 2.4(6) . . . . ?
C42 C41 C46 C47 -178.3(4) . . . . ?
C42 C43 C57 C45 2.8(7) . . . . ?
C42 C43 C57 C56 -176.7(5) . . . . ?
C45 C46 C47 C48 -1.9(6) . . . . ?
C45 C50 C54 C53 177.4(4) . . . . ?
C45 C50 C54 C55 -1.6(6) . . . . ?
C46 C41 C42 C43 -2.0(7) . . . . ?
C46 C45 C50 C49 3.1(6) . . . . ?
C46 C45 C50 C54 -175.5(4) . . . . ?
C46 C45 C57 C43 -2.3(6) . . . . ?
C46 C45 C57 C56 177.2(4) . . . . ?
C46 C47 C48 C49 2.7(7) . . . . ?
C47 C48 C49 C50 -0.5(7) . . . . ?
C47 C48 C49 C51 177.9(4) . . . . ?
C48 C49 C50 C45 -2.4(6) . . . . ?
C48 C49 C50 C54 176.2(4) . . . . ?
C48 C49 C51 C52 -174.6(4) . . . . ?
C49 C50 C54 C53 -1.2(6) . . . . ?
C49 C50 C54 C55 179.9(4) . . . . ?
C49 C51 C52 C53 -1.9(8) . . . . ?
C50 C45 C46 C41 178.4(4) . . . . ?
C50 C45 C46 C47 -0.9(6) . . . . ?
C50 C45 C57 C43 179.0(4) . . . . ?
C50 C45 C57 C56 -1.5(6) . . . . ?
C50 C49 C51 C52 3.8(7) . . . . ?
C50 C54 C55 C56 -2.0(7) . . . . ?
C51 C49 C50 C45 179.2(4) . . . . ?
C51 C49 C50 C54 -2.2(6) . . . . ?
C51 C52 C53 C54 -1.7(8) . . . . ?
C52 C53 C54 C50 3.1(7) . . . . ?
C52 C53 C54 C55 -178.0(4) . . . . ?
C53 C54 C55 C56 179.1(5) . . . . ?
C54 C55 C56 C57 3.8(8) . . . . ?
C55 C56 C57 C43 177.5(5) . . . . ?
C55 C56 C57 C45 -2.1(7) . . . . ?
C57 C45 C46 C41 -0.3(6) . . . . ?
C57 C45 C46 C47 -179.6(4) . . . . ?
C57 C45 C50 C49 -178.2(4) . . . . ?
C57 C45 C50 C54 3.2(6) . . . . ?
