#------------------------------------------------------------------------------
#$Date: 2024-02-04 14:16:58 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289567 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/78/7247835.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_7247835
loop_
_publ_author_name
'Yang, Zhi'
'Chen, Yu'
'Wan, Linxi'
'Li, Yuxiao'
'Chen, Dan'
'Tao, Jianlin'
'Tang, Pei'
'Chen, Fen-Er'
_publ_section_title
;
 Iridium-catalyzed asymmetric, complete hydrogenation of pyrimidinium
 salts under batch and flow
;
_journal_issue                   1
_journal_name_full               'Green Chemistry'
_journal_page_first              317
_journal_page_last               322
_journal_paper_doi               10.1039/D3GC04364A
_journal_volume                  26
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H24 N2'
_chemical_formula_sum            'C23 H24 N2'
_chemical_formula_weight         328.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2f5650
_audit_creation_date             2022-11-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-02-01 deposited with the CCDC.	2023-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.9340(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.1560(3)
_cell_length_b                   6.05280(10)
_cell_length_c                   20.8658(4)
_cell_measurement_reflns_used    9863
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      69.874
_cell_measurement_theta_min      2.192
_cell_volume                     1849.50(6)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0513
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            33674
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         2.191
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.525
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5309
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1321 before and 0.0648 after correction.
The Ratio of minimum to maximum transmission is 0.7048.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 2400 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         6569
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0457
_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)+(0.0770P)²+0.1019P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1257
_reflns_Friedel_coverage         0.808
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                5814
_reflns_number_total             6569
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3gc04364a2.cif
_cod_data_source_block           cu_tp_cy001_0ma_a
_cod_depositor_comments          'Adding full bibliography for 7247835.cif.'
_cod_database_code               7247835
_shelx_shelxl_version_number     2014/7
_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   0.907
_shelx_estimated_absorpt_t_min   0.798
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Riding coordinates:
 N3(H3a)
2.b Ternary CH refined with riding coordinates:
 C8(H8), C32(H32)
2.c Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b), C6(H6a,H6b), C23(H23a,H23b), C24(H24a,H24b), C29(H29a,H29b),
 C30(H30a,H30b), C31(H31a,H31b), C45(H45a,H45b)
2.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26),
  C27(H27), C34(H34), C35(H35), C38(H38), C39(H39), C40(H40), C41(H41),
 C42(H42), C43(H43), C44(H44), C46(H46), C47(H47)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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
N1 N 0.41820(15) 0.5764(3) 0.69912(11) 0.0553(5) Uani 1 1 d . . . . .
N2 N 0.89882(14) 0.3872(3) 0.76535(10) 0.0537(5) Uani 1 1 d . . . . .
N3 N 0.84908(16) 0.5497(4) 0.65582(10) 0.0566(5) Uani 1 1 d . . . . .
H3A H 0.8991 0.6117 0.6533 0.068 Uiso 1 1 d R U . . .
C1 C 0.6056(2) 0.9881(6) 0.56989(14) 0.0707(8) Uani 1 1 d . . . . .
H1 H 0.6484 1.0740 0.5563 0.085 Uiso 1 1 calc R U . . .
C2 C 0.5169(2) 1.0569(5) 0.55729(14) 0.0677(7) Uani 1 1 d . . . . .
H2 H 0.4994 1.1909 0.5360 0.081 Uiso 1 1 calc R U . . .
C3 C 0.45369(19) 0.9267(5) 0.57630(14) 0.0617(7) Uani 1 1 d . . . . .
H3 H 0.3933 0.9738 0.5674 0.074 Uiso 1 1 calc R U . . .
C4 C 0.47783(18) 0.7268(4) 0.60848(12) 0.0557(6) Uani 1 1 d . . . . .
C5 C 0.4080(2) 0.5825(5) 0.62768(14) 0.0670(7) Uani 1 1 d . . . . .
H5A H 0.3474 0.6364 0.6059 0.080 Uiso 1 1 calc R U . . .
H5B H 0.4133 0.4334 0.6120 0.080 Uiso 1 1 calc R U . . .
C6 C 0.3553(2) 0.4144(5) 0.71447(16) 0.0693(8) Uani 1 1 d . . . . .
H6A H 0.2933 0.4573 0.6922 0.083 Uiso 1 1 calc R U . . .
H6B H 0.3668 0.2720 0.6969 0.083 Uiso 1 1 calc R U . . .
N7 N 0.36235(19) 0.3910(4) 0.78444(13) 0.0652(6) Uani 1 1 d . . . . .
H7 H 0.419(2) 0.348(6) 0.8065(16) 0.078 Uiso 1 1 d . U . . .
C8 C 0.34543(17) 0.6011(4) 0.81346(14) 0.0547(6) Uani 1 1 d . . . . .
H8 H 0.2825 0.6434 0.7916 0.066 Uiso 1 1 calc R U . . .
C9 C 0.35175(17) 0.5855(4) 0.88667(14) 0.0564(6) Uani 1 1 d . . . . .
C10 C 0.3853(2) 0.4014(5) 0.92511(15) 0.0675(7) Uani 1 1 d . . . . .
H10 H 0.4049 0.2798 0.9052 0.081 Uiso 1 1 calc R U . . .
C11 C 0.3903(2) 0.3947(5) 0.99224(16) 0.0685(7) Uani 1 1 d . . . . .
H11 H 0.4132 0.2692 1.0166 0.082 Uiso 1 1 calc R U . . .
C12 C 0.36153(17) 0.5729(5) 1.02397(14) 0.0592(6) Uani 1 1 d . . . . .
C13 C 0.36377(17) 0.5678(5) 1.09556(14) 0.0610(6) Uani 1 1 d . . . . .
C14 C 0.3947(2) 0.7457(6) 1.13654(15) 0.0705(8) Uani 1 1 d . . . . .
H14 H 0.4136 0.8724 1.1186 0.085 Uiso 1 1 calc R U . . .
C15 C 0.3983(2) 0.7412(7) 1.20336(16) 0.0793(9) Uani 1 1 d . . . . .
H15 H 0.4202 0.8628 1.2300 0.095 Uiso 1 1 calc R U . . .
C16 C 0.3696(2) 0.5565(7) 1.23019(17) 0.0821(10) Uani 1 1 d . . . . .
H16 H 0.3718 0.5523 1.2751 0.098 Uiso 1 1 calc R U . . .
C17 C 0.6318(2) 0.7916(6) 0.60273(14) 0.0714(8) Uani 1 1 d . . . . .
H17 H 0.6925 0.7464 0.6121 0.086 Uiso 1 1 calc R U . . .
C18 C 0.56811(19) 0.6623(5) 0.62171(13) 0.0627(7) Uani 1 1 d . . . . .
H18 H 0.5862 0.5298 0.6437 0.075 Uiso 1 1 calc R U . . .
C19 C 0.3302(2) 0.7587(5) 0.98595(14) 0.0667(7) Uani 1 1 d . . . . .
H19 H 0.3122 0.8820 1.0060 0.080 Uiso 1 1 calc R U . . .
C20 C 0.3253(2) 0.7641(5) 0.91914(15) 0.0671(7) Uani 1 1 d . . . . .
H20 H 0.3036 0.8910 0.8951 0.080 Uiso 1 1 calc R U . . .
C21 C 0.3375(2) 0.3776(7) 1.19046(19) 0.0850(10) Uani 1 1 d . . . . .
H21 H 0.3175 0.2528 1.2086 0.102 Uiso 1 1 calc R U . . .
C22 C 0.3347(2) 0.3814(6) 1.12381(17) 0.0735(8) Uani 1 1 d . . . . .
H22 H 0.3133 0.2588 1.0975 0.088 Uiso 1 1 calc R U . . .
C23 C 0.4069(2) 0.7820(4) 0.79786(14) 0.0595(6) Uani 1 1 d . . . . .
H23A H 0.3894 0.9234 0.8126 0.071 Uiso 1 1 calc R U . . .
H23B H 0.4697 0.7530 0.8218 0.071 Uiso 1 1 calc R U . . .
C24 C 0.40002(19) 0.7922(4) 0.72418(13) 0.0561(6) Uani 1 1 d . . . . .
H24A H 0.3393 0.8409 0.7007 0.067 Uiso 1 1 calc R U . . .
H24B H 0.4436 0.8990 0.7160 0.067 Uiso 1 1 calc R U . . .
C25 C 1.0988(3) 0.0133(8) 0.96347(17) 0.0934(12) Uani 1 1 d . . . . .
H25 H 1.1441 -0.0713 0.9914 0.112 Uiso 1 1 calc R U . . .
C26 C 1.1210(2) 0.2085(9) 0.93832(17) 0.0928(12) Uani 1 1 d . . . . .
H26 H 1.1814 0.2560 0.9491 0.111 Uiso 1 1 calc R U . . .
C27 C 1.0532(2) 0.3368(6) 0.89657(14) 0.0742(8) Uani 1 1 d . . . . .
H27 H 1.0687 0.4695 0.8798 0.089 Uiso 1 1 calc R U . . .
C28 C 0.96416(19) 0.2682(5) 0.88028(12) 0.0580(6) Uani 1 1 d . . . . .
C29 C 0.8905(2) 0.4005(5) 0.83368(13) 0.0671(7) Uani 1 1 d . . . . .
H29A H 0.8312 0.3452 0.8355 0.080 Uiso 1 1 calc R U . . .
H29B H 0.8948 0.5537 0.8478 0.080 Uiso 1 1 calc R U . . .
C30 C 0.87891(19) 0.1655(4) 0.73802(13) 0.0561(6) Uani 1 1 d . . . . .
H30A H 0.8166 0.1261 0.7373 0.067 Uiso 1 1 calc R U . . .
H30B H 0.9195 0.0601 0.7660 0.067 Uiso 1 1 calc R U . . .
C31 C 0.8911(2) 0.1550(4) 0.66851(12) 0.0572(6) Uani 1 1 d . . . . .
H31A H 0.8725 0.0106 0.6497 0.069 Uiso 1 1 calc R U . . .
H31B H 0.9551 0.1750 0.6700 0.069 Uiso 1 1 calc R U . . .
C32 C 0.83486(17) 0.3321(4) 0.62463(12) 0.0511(6) Uani 1 1 d . . . . .
H32 H 0.7706 0.2942 0.6197 0.061 Uiso 1 1 calc R U . . .
C33 C 0.84853(16) 0.3428(4) 0.55505(12) 0.0511(6) Uani 1 1 d . . . . .
C34 C 0.8134(3) 0.5128(6) 0.51300(16) 0.0877(11) Uani 1 1 d . . . . .
H34 H 0.7823 0.6259 0.5280 0.105 Uiso 1 1 calc R U . . .
C35 C 0.8227(3) 0.5216(6) 0.44880(16) 0.0888(11) Uani 1 1 d . . . . .
H35 H 0.7972 0.6401 0.4220 0.107 Uiso 1 1 calc R U . . .
C36 C 0.86767(16) 0.3642(4) 0.42353(12) 0.0520(6) Uani 1 1 d . . . . .
C37 C 0.87652(15) 0.3722(4) 0.35406(12) 0.0518(6) Uani 1 1 d . . . . .
C38 C 0.8484(2) 0.5540(5) 0.31371(15) 0.0668(7) Uani 1 1 d . . . . .
H38 H 0.8243 0.6754 0.3307 0.080 Uiso 1 1 calc R U . . .
C39 C 0.8552(2) 0.5603(6) 0.24878(16) 0.0744(8) Uani 1 1 d . . . . .
H39 H 0.8352 0.6841 0.2227 0.089 Uiso 1 1 calc R U . . .
C40 C 0.89134(19) 0.3849(6) 0.22304(14) 0.0691(8) Uani 1 1 d . . . . .
H40 H 0.8970 0.3897 0.1797 0.083 Uiso 1 1 calc R U . . .
C41 C 0.9192(2) 0.2014(6) 0.26164(14) 0.0705(8) Uani 1 1 d . . . . .
H41 H 0.9435 0.0812 0.2443 0.085 Uiso 1 1 calc R U . . .
C42 C 0.91149(19) 0.1946(5) 0.32611(14) 0.0623(7) Uani 1 1 d . . . . .
H42 H 0.9301 0.0684 0.3514 0.075 Uiso 1 1 calc R U . . .
C43 C 0.9042(4) 0.1977(7) 0.46580(18) 0.1193(18) Uani 1 1 d . . . . .
H43 H 0.9366 0.0870 0.4510 0.143 Uiso 1 1 calc R U . . .
C44 C 0.8951(4) 0.1864(7) 0.53017(19) 0.1162(18) Uani 1 1 d . . . . .
H44 H 0.9214 0.0688 0.5570 0.139 Uiso 1 1 calc R U . . .
C45 C 0.8382(2) 0.5443(5) 0.72277(14) 0.0639(7) Uani 1 1 d . . . . .
H45A H 0.7755 0.5060 0.7211 0.077 Uiso 1 1 calc R U . . .
H45B H 0.8498 0.6906 0.7420 0.077 Uiso 1 1 calc R U . . .
C46 C 0.9438(2) 0.0705(5) 0.90636(14) 0.0678(7) Uani 1 1 d . . . . .
H46 H 0.8835 0.0218 0.8959 0.081 Uiso 1 1 calc R U . . .
C47 C 1.0105(3) -0.0567(6) 0.94755(15) 0.0816(9) Uani 1 1 d . . . . .
H47 H 0.9952 -0.1896 0.9643 0.098 Uiso 1 1 calc R U . . .
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
C5 N1 C6 109.7(2) . . ?
C5 N1 C24 111.3(2) . . ?
C24 N1 C6 109.2(2) . . ?
C30 N2 C29 111.7(2) . . ?
C45 N2 C29 111.0(2) . . ?
C45 N2 C30 109.1(2) . . ?
C32 N3 H3A 113.5 . . ?
C45 N3 H3A 112.9 . . ?
C45 N3 C32 111.7(2) . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C17 120.1(3) . . ?
C17 C1 H1 120.0 . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.5(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 121.3(3) . . ?
C18 C4 C3 117.9(3) . . ?
C18 C4 C5 120.8(3) . . ?
N1 C5 C4 113.0(2) . . ?
N1 C5 H5A 109.0 . . ?
N1 C5 H5B 109.0 . . ?
C4 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
N1 C6 H6A 108.8 . . ?
N1 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
N7 C6 N1 113.9(2) . . ?
N7 C6 H6A 108.8 . . ?
N7 C6 H6B 108.8 . . ?
C6 N7 H7 111(2) . . ?
C6 N7 C8 111.1(2) . . ?
C8 N7 H7 107(2) . . ?
N7 C8 H8 106.8 . . ?
N7 C8 C9 113.2(2) . . ?
N7 C8 C23 110.7(2) . . ?
C9 C8 H8 106.8 . . ?
C9 C8 C23 112.2(2) . . ?
C23 C8 H8 106.8 . . ?
C10 C9 C8 123.6(2) . . ?
C20 C9 C8 119.6(2) . . ?
C20 C9 C10 116.8(3) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.6(3) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.1(3) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C13 122.2(3) . . ?
C19 C12 C11 117.3(3) . . ?
C19 C12 C13 120.5(3) . . ?
C14 C13 C12 121.5(3) . . ?
C14 C13 C22 117.6(3) . . ?
C22 C13 C12 120.9(3) . . ?
C13 C14 H14 119.0 . . ?
C13 C14 C15 121.9(3) . . ?
C15 C14 H14 119.0 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.6(4) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C21 119.8(3) . . ?
C21 C16 H16 120.1 . . ?
C1 C17 H17 120.0 . . ?
C18 C17 C1 119.9(3) . . ?
C18 C17 H17 120.0 . . ?
C4 C18 H18 119.5 . . ?
C17 C18 C4 120.9(3) . . ?
C17 C18 H18 119.5 . . ?
C12 C19 H19 119.4 . . ?
C20 C19 C12 121.3(3) . . ?
C20 C19 H19 119.4 . . ?
C9 C20 H20 119.1 . . ?
C19 C20 C9 121.9(3) . . ?
C19 C20 H20 119.1 . . ?
C16 C21 H21 119.7 . . ?
C16 C21 C22 120.6(3) . . ?
C22 C21 H21 119.7 . . ?
C13 C22 H22 119.7 . . ?
C21 C22 C13 120.5(3) . . ?
C21 C22 H22 119.7 . . ?
C8 C23 H23A 109.4 . . ?
C8 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C24 C23 C8 111.1(2) . . ?
C24 C23 H23A 109.4 . . ?
C24 C23 H23B 109.4 . . ?
N1 C24 C23 110.9(2) . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 108.0 . . ?
C26 C25 H25 120.1 . . ?
C47 C25 H25 120.1 . . ?
C47 C25 C26 119.8(4) . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.3(4) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.3(3) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 C29 121.2(3) . . ?
C27 C28 C46 118.1(3) . . ?
C46 C28 C29 120.7(3) . . ?
N2 C29 C28 111.3(2) . . ?
N2 C29 H29A 109.4 . . ?
N2 C29 H29B 109.4 . . ?
C28 C29 H29A 109.4 . . ?
C28 C29 H29B 109.4 . . ?
H29A C29 H29B 108.0 . . ?
N2 C30 H30A 109.6 . . ?
N2 C30 H30B 109.6 . . ?
N2 C30 C31 110.5(2) . . ?
H30A C30 H30B 108.1 . . ?
C31 C30 H30A 109.6 . . ?
C31 C30 H30B 109.6 . . ?
C30 C31 H31A 109.4 . . ?
C30 C31 H31B 109.4 . . ?
C30 C31 C32 111.1(2) . . ?
H31A C31 H31B 108.0 . . ?
C32 C31 H31A 109.4 . . ?
C32 C31 H31B 109.4 . . ?
N3 C32 C31 111.84(19) . . ?
N3 C32 H32 106.6 . . ?
N3 C32 C33 110.3(2) . . ?
C31 C32 H32 106.6 . . ?
C33 C32 C31 114.3(2) . . ?
C33 C32 H32 106.6 . . ?
C34 C33 C32 121.2(2) . . ?
C44 C33 C32 123.1(2) . . ?
C44 C33 C34 115.6(3) . . ?
C33 C34 H34 119.0 . . ?
C33 C34 C35 122.0(3) . . ?
C35 C34 H34 119.0 . . ?
C34 C35 H35 118.8 . . ?
C36 C35 C34 122.4(3) . . ?
C36 C35 H35 118.8 . . ?
C35 C36 C37 122.4(2) . . ?
C35 C36 C43 115.5(3) . . ?
C43 C36 C37 122.1(2) . . ?
C38 C37 C36 121.8(2) . . ?
C38 C37 C42 116.7(2) . . ?
C42 C37 C36 121.5(2) . . ?
C37 C38 H38 119.1 . . ?
C37 C38 C39 121.9(3) . . ?
C39 C38 H38 119.1 . . ?
C38 C39 H39 120.0 . . ?
C40 C39 C38 120.1(3) . . ?
C40 C39 H39 120.0 . . ?
C39 C40 H40 120.3 . . ?
C39 C40 C41 119.5(3) . . ?
C41 C40 H40 120.3 . . ?
C40 C41 H41 119.8 . . ?
C40 C41 C42 120.3(3) . . ?
C42 C41 H41 119.8 . . ?
C37 C42 H42 119.3 . . ?
C41 C42 C37 121.5(3) . . ?
C41 C42 H42 119.3 . . ?
C36 C43 H43 118.7 . . ?
C36 C43 C44 122.6(3) . . ?
C44 C43 H43 118.7 . . ?
C33 C44 C43 121.7(3) . . ?
C33 C44 H44 119.1 . . ?
C43 C44 H44 119.1 . . ?
N2 C45 H45A 109.0 . . ?
N2 C45 H45B 109.0 . . ?
N3 C45 N2 113.1(2) . . ?
N3 C45 H45A 109.0 . . ?
N3 C45 H45B 109.0 . . ?
H45A C45 H45B 107.8 . . ?
C28 C46 H46 119.2 . . ?
C47 C46 C28 121.7(3) . . ?
C47 C46 H46 119.2 . . ?
C25 C47 C46 119.7(4) . . ?
C25 C47 H47 120.2 . . ?
C46 C47 H47 120.2 . . ?
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 C5 1.459(3) . ?
N1 C6 1.460(4) . ?
N1 C24 1.459(3) . ?
N2 C29 1.465(3) . ?
N2 C30 1.459(3) . ?
N2 C45 1.455(3) . ?
N3 H3A 0.8601 . ?
N3 C32 1.460(3) . ?
N3 C45 1.449(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.367(5) . ?
C1 C17 1.379(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(4) . ?
C4 C5 1.504(4) . ?
C4 C18 1.381(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 N7 1.443(4) . ?
N7 H7 0.90(3) . ?
N7 C8 1.459(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.509(4) . ?
C8 C23 1.526(4) . ?
C9 C10 1.390(4) . ?
C9 C20 1.389(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.393(4) . ?
C12 C13 1.486(4) . ?
C12 C19 1.387(4) . ?
C13 C14 1.380(5) . ?
C13 C22 1.396(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.381(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.371(6) . ?
C16 H16 0.9300 . ?
C16 C21 1.374(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.377(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.380(5) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.515(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25 0.9300 . ?
C25 C26 1.369(7) . ?
C25 C47 1.361(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.398(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.368(4) . ?
C28 C29 1.508(4) . ?
C28 C46 1.383(4) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C31 1.510(4) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 C32 1.520(4) . ?
C32 H32 0.9800 . ?
C32 C33 1.520(3) . ?
C33 C34 1.368(4) . ?
C33 C44 1.361(4) . ?
C34 H34 0.9300 . ?
C34 C35 1.384(4) . ?
C35 H35 0.9300 . ?
C35 C36 1.355(4) . ?
C36 C37 1.490(3) . ?
C36 C43 1.360(4) . ?
C37 C38 1.384(4) . ?
C37 C42 1.392(4) . ?
C38 H38 0.9300 . ?
C38 C39 1.386(4) . ?
C39 H39 0.9300 . ?
C39 C40 1.366(5) . ?
C40 H40 0.9300 . ?
C40 C41 1.373(5) . ?
C41 H41 0.9300 . ?
C41 C42 1.381(4) . ?
C42 H42 0.9300 . ?
C43 H43 0.9300 . ?
C43 C44 1.387(5) . ?
C44 H44 0.9300 . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 H46 0.9300 . ?
C46 C47 1.381(5) . ?
C47 H47 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
N1 C6 N7 C8 58.5(3) . . . . ?
N2 C30 C31 C32 -54.1(3) . . . . ?
N3 C32 C33 C34 -43.3(4) . . . . ?
N3 C32 C33 C44 137.2(4) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C1 C17 C18 C4 -0.2(4) . . . . ?
C2 C1 C17 C18 1.3(4) . . . . ?
C2 C3 C4 C5 -178.5(2) . . . . ?
C2 C3 C4 C18 0.7(4) . . . . ?
C3 C4 C5 N1 -109.2(3) . . . . ?
C3 C4 C18 C17 -0.8(4) . . . . ?
C5 N1 C6 N7 178.1(2) . . . . ?
C5 N1 C24 C23 177.6(2) . . . . ?
C5 C4 C18 C17 178.4(3) . . . . ?
C6 N1 C5 C4 -173.5(3) . . . . ?
C6 N1 C24 C23 56.4(3) . . . . ?
C6 N7 C8 C9 179.8(2) . . . . ?
C6 N7 C8 C23 -53.2(3) . . . . ?
N7 C8 C9 C10 10.4(4) . . . . ?
N7 C8 C9 C20 -171.3(3) . . . . ?
N7 C8 C23 C24 51.9(3) . . . . ?
C8 C9 C10 C11 179.7(3) . . . . ?
C8 C9 C20 C19 -179.6(3) . . . . ?
C8 C23 C24 N1 -54.1(3) . . . . ?
C9 C8 C23 C24 179.4(2) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C10 C9 C20 C19 -1.2(4) . . . . ?
C10 C11 C12 C13 178.3(3) . . . . ?
C10 C11 C12 C19 -1.7(4) . . . . ?
C11 C12 C13 C14 136.4(3) . . . . ?
C11 C12 C13 C22 -43.4(4) . . . . ?
C11 C12 C19 C20 1.8(4) . . . . ?
C12 C13 C14 C15 -179.0(3) . . . . ?
C12 C13 C22 C21 179.6(3) . . . . ?
C12 C19 C20 C9 -0.4(5) . . . . ?
C13 C12 C19 C20 -178.2(3) . . . . ?
C13 C14 C15 C16 -0.8(5) . . . . ?
C14 C13 C22 C21 -0.2(4) . . . . ?
C14 C15 C16 C21 0.1(5) . . . . ?
C15 C16 C21 C22 0.6(5) . . . . ?
C16 C21 C22 C13 -0.5(5) . . . . ?
C17 C1 C2 C3 -1.4(4) . . . . ?
C18 C4 C5 N1 71.6(3) . . . . ?
C19 C12 C13 C14 -43.6(4) . . . . ?
C19 C12 C13 C22 136.6(3) . . . . ?
C20 C9 C10 C11 1.3(4) . . . . ?
C22 C13 C14 C15 0.9(4) . . . . ?
C23 C8 C9 C10 -115.8(3) . . . . ?
C23 C8 C9 C20 62.5(3) . . . . ?
C24 N1 C5 C4 65.5(3) . . . . ?
C24 N1 C6 N7 -59.7(3) . . . . ?
C25 C26 C27 C28 -0.2(5) . . . . ?
C26 C25 C47 C46 -0.3(6) . . . . ?
C26 C27 C28 C29 -178.1(3) . . . . ?
C26 C27 C28 C46 0.2(4) . . . . ?
C27 C28 C29 N2 71.2(3) . . . . ?
C27 C28 C46 C47 -0.2(4) . . . . ?
C28 C46 C47 C25 0.3(5) . . . . ?
C29 N2 C30 C31 -178.1(2) . . . . ?
C29 N2 C45 N3 175.4(2) . . . . ?
C29 C28 C46 C47 178.0(3) . . . . ?
C30 N2 C29 C28 67.8(3) . . . . ?
C30 N2 C45 N3 -61.0(3) . . . . ?
C30 C31 C32 N3 49.7(3) . . . . ?
C30 C31 C32 C33 176.0(2) . . . . ?
C31 C32 C33 C34 -170.3(3) . . . . ?
C31 C32 C33 C44 10.2(4) . . . . ?
C32 N3 C45 N2 57.1(3) . . . . ?
C32 C33 C34 C35 -177.9(3) . . . . ?
C32 C33 C44 C43 178.2(4) . . . . ?
C33 C34 C35 C36 -0.5(7) . . . . ?
C34 C33 C44 C43 -1.3(7) . . . . ?
C34 C35 C36 C37 179.1(3) . . . . ?
C34 C35 C36 C43 -0.8(6) . . . . ?
C35 C36 C37 C38 7.6(4) . . . . ?
C35 C36 C37 C42 -170.8(3) . . . . ?
C35 C36 C43 C44 1.1(7) . . . . ?
C36 C37 C38 C39 -178.9(3) . . . . ?
C36 C37 C42 C41 179.6(2) . . . . ?
C36 C43 C44 C33 0.0(8) . . . . ?
C37 C36 C43 C44 -178.8(4) . . . . ?
C37 C38 C39 C40 -0.7(5) . . . . ?
C38 C37 C42 C41 1.2(4) . . . . ?
C38 C39 C40 C41 1.1(5) . . . . ?
C39 C40 C41 C42 -0.4(5) . . . . ?
C40 C41 C42 C37 -0.7(4) . . . . ?
C42 C37 C38 C39 -0.5(4) . . . . ?
C43 C36 C37 C38 -172.5(4) . . . . ?
C43 C36 C37 C42 9.1(5) . . . . ?
C44 C33 C34 C35 1.6(6) . . . . ?
C45 N2 C29 C28 -170.1(2) . . . . ?
C45 N2 C30 C31 58.7(3) . . . . ?
C45 N3 C32 C31 -50.5(3) . . . . ?
C45 N3 C32 C33 -178.96(19) . . . . ?
C46 C28 C29 N2 -107.0(3) . . . . ?
C47 C25 C26 C27 0.3(6) . . . . ?
