#------------------------------------------------------------------------------
#$Date: 2024-04-17 04:38:50 +0300 (Wed, 17 Apr 2024) $
#$Revision: 291248 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/84/7248428.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_7248428
loop_
_publ_author_name
'Antoniou, Ioakeim M.'
'Ioannou, Natalia'
'Panagiotou, Nikos'
'Georgiades, Savvas N.'
_publ_section_title
;
 LED-induced Ru-photoredox Pd-catalyzed C--H arylation of
 (6-phenylpyridin-2-yl)pyrimidines and heteroaryl counterparts
;
_journal_issue                   17
_journal_name_full               'RSC Advances'
_journal_page_first              12179
_journal_page_last               12191
_journal_paper_doi               10.1039/D4RA02173H
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C31 H26 N4 O2'
_chemical_formula_sum            'C31 H26 N4 O2'
_chemical_formula_weight         486.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-28
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-11-12 deposited with the CCDC.	2024-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.5518(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.8184(4)
_cell_length_b                   8.96166(12)
_cell_length_c                   18.6116(2)
_cell_measurement_reflns_used    12195
_cell_measurement_temperature    179.98(10)
_cell_measurement_theta_max      76.1980
_cell_measurement_theta_min      4.7370
_cell_volume                     5124.01(11)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -40.00   0.50    0.50    --  -47.44 -70.00  94.00  160
  2  ω    -44.00  12.00   0.50    0.50    --  -47.44  70.00-134.00  112
  3  ω     84.00 120.00   0.50    0.50    --   47.44  70.00-134.00   72
  4  ω     14.00  65.00   0.50    0.50    --   47.44 -70.00  94.00  102
  5  ω   -158.00 -86.00   0.50    2.00    -- -106.00 -70.00  94.00  144
  6  ω    -80.00 -37.00   0.50    2.00    -- -106.00  70.00-134.00   86
  7  ω     34.00  71.00   0.50    2.00    --  106.24 -70.00  94.00   74
  8  ω     89.00 149.00   0.50    2.00    --  106.24  70.00-134.00  120
  9  ω    -28.00  23.00   0.50    0.50    --  -47.44  19.00-150.00  102
 10  ω     18.00  91.00   0.50    0.50    --   47.44-126.00  90.00  146
 11  ω     -3.00  25.00   0.50    0.50    --   47.44 -19.00  90.00   56
 12  ω    -15.00  29.00   0.50    0.50    --   47.44 -19.00-120.00   88
 13  ω     81.00 117.00   0.50    0.50    --   47.44 126.00  90.00   72
 14  ω     85.00 118.00   0.50    0.50    --   47.44 126.00 -30.00   66
 15  ω    -70.00 -45.00   0.50    2.00    -- -106.00  61.00 -90.00   50
 16  ω   -176.00 -93.00   0.50    2.00    -- -106.00 -45.00 -30.00  166
 17  ω   -108.00 -78.00   0.50    2.00    -- -106.00 111.00  46.63   60
 18  ω   -112.00 -37.00   0.50    2.00    -- -106.00 126.00-120.00  150
 19  ω    -97.00 -35.00   0.50    2.00    -- -106.00  77.00 -90.00  124
 20  ω   -175.00-127.00   0.50    2.00    -- -106.00 -45.00 150.00   96
 21  ω     39.00  64.00   0.50    2.00    --  106.24-126.00-120.00   50
 22  ω     34.00  59.00   0.50    2.00    --  106.24 -61.00   0.00   50
 23  ω     40.00  66.00   0.50    2.00    --  106.24 -61.00 -30.00   52
 24  ω     37.00  99.00   0.50    2.00    --  106.24 -95.00 120.00  124
 25  ω     48.00 111.00   0.50    2.00    --  106.24-126.00   0.00  126
 26  ω    126.00 170.00   0.50    2.00    --  106.24  30.00 -90.00   88
 27  ω     55.00 104.00   0.50    2.00    --  106.24 -95.00 150.00   98
 28  ω     36.00 101.00   0.50    2.00    --  106.24-126.00  90.00  130
 29  ω     95.00 170.00   0.50    2.00    --  106.24  45.00-180.00  150
 30  ω     36.00 109.00   0.50    2.00    --  106.24-126.00  60.00  146
 31  ω     88.00 113.00   0.50    2.00    --  106.24-126.00-120.00   50
 32  ω     34.00  60.00   0.50    2.00    --  106.24 -61.00  60.00   52
 33  ω     98.00 176.00   0.50    2.00    --  106.24  45.00 150.00  156
 34  ω     40.00  65.00   0.50    2.00    --  106.24 -61.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0371510000
_diffrn_orient_matrix_UB_12      0.0329357000
_diffrn_orient_matrix_UB_13      -0.0484179000
_diffrn_orient_matrix_UB_21      -0.0134002000
_diffrn_orient_matrix_UB_22      0.1655965000
_diffrn_orient_matrix_UB_23      -0.0034626000
_diffrn_orient_matrix_UB_31      0.0309031000
_diffrn_orient_matrix_UB_32      0.0321550000
_diffrn_orient_matrix_UB_33      0.0673846000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27427
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.997
_diffrn_reflns_theta_max         66.997
_diffrn_reflns_theta_min         2.877
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       block
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.049
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4572
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0373
_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)+(0.0488P)²+2.0156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1017
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3876
_reflns_number_total             4572
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra02173h2.cif
_cod_data_source_block           ima_2me_auto
_cod_original_cell_volume        5124.01(12)
_cod_database_code               7248428
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'O N C H'
_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   0.982
_shelx_estimated_absorpt_t_min   0.969
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N12(H12), C18(H18), C33(H33), C37(H37), C14(H14), C34(H34), C35(H35),
 C22(H22), C24(H24), C17(H17), C15(H15), C29(H29), C36(H36), C23(H23), C16(H16),
  C27(H27), C28(H28)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C31(H31A,H31B,H31C), C8(H8A,H8B,H8C)
;
_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 1.082
_oxdiff_exptl_absorpt_empirical_full_min 0.949
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
O11 O 0.36373(3) 0.79358(10) 0.68040(5) 0.0435(2) Uani 1 1 d . . . . .
N12 N 0.42539(3) 0.78013(12) 0.62021(6) 0.0367(3) Uani 1 1 d . . . . .
H12 H 0.452156 0.745174 0.623273 0.044 Uiso 1 1 calc R U . . .
O7 O 0.50261(4) 0.48281(13) 0.89459(6) 0.0600(3) Uani 1 1 d . . . . .
N20 N 0.37864(3) 0.46945(12) 0.63886(6) 0.0361(3) Uani 1 1 d . . . . .
N3 N 0.45140(4) 0.44853(13) 0.79939(6) 0.0400(3) Uani 1 1 d . . . . .
N1 N 0.47671(4) 0.68819(14) 0.83950(6) 0.0438(3) Uani 1 1 d . . . . .
C10 C 0.40072(4) 0.74839(14) 0.67528(7) 0.0355(3) Uani 1 1 d . . . . .
C5 C 0.42599(4) 0.66619(14) 0.73565(7) 0.0358(3) Uani 1 1 d . . . . .
C13 C 0.41192(4) 0.86455(14) 0.55816(7) 0.0368(3) Uani 1 1 d . . . . .
C4 C 0.42624(4) 0.51234(14) 0.74529(7) 0.0354(3) Uani 1 1 d . . . . .
C19 C 0.39865(4) 0.40960(14) 0.69854(7) 0.0374(3) Uani 1 1 d . . . . .
C21 C 0.35192(4) 0.38327(15) 0.59673(7) 0.0389(3) Uani 1 1 d . . . . .
C32 C 0.26052(4) 0.45837(15) 0.59991(7) 0.0393(3) Uani 1 1 d . . . . .
C2 C 0.47544(4) 0.53888(17) 0.84149(7) 0.0424(3) Uani 1 1 d . . . . .
C6 C 0.45126(5) 0.75085(15) 0.78643(7) 0.0409(3) Uani 1 1 d . . . . .
C25 C 0.32832(5) 0.45531(15) 0.53244(7) 0.0409(3) Uani 1 1 d . . . . .
C18 C 0.44158(5) 0.96195(16) 0.53110(7) 0.0422(3) Uani 1 1 d . . . . .
H18 H 0.470027 0.971001 0.554357 0.051 Uiso 1 1 calc R U . . .
C30 C 0.28393(5) 0.48700(15) 0.53409(7) 0.0417(3) Uani 1 1 d . . . . .
C33 C 0.22910(5) 0.34733(16) 0.60135(8) 0.0455(3) Uani 1 1 d . . . . .
H33 H 0.222951 0.285936 0.560185 0.055 Uiso 1 1 calc R U . . .
C37 C 0.26926(5) 0.54490(17) 0.66121(8) 0.0471(3) Uani 1 1 d . . . . .
H37 H 0.291255 0.619290 0.661997 0.057 Uiso 1 1 calc R U . . .
C14 C 0.37056(5) 0.85034(16) 0.52392(8) 0.0451(3) Uani 1 1 d . . . . .
H14 H 0.350154 0.783690 0.542232 0.054 Uiso 1 1 calc R U . . .
C34 C 0.20668(5) 0.32512(17) 0.66201(9) 0.0497(4) Uani 1 1 d . . . . .
H34 H 0.185538 0.248046 0.662423 0.060 Uiso 1 1 calc R U . . .
C35 C 0.21489(5) 0.41413(18) 0.72159(9) 0.0518(4) Uani 1 1 d . . . . .
H35 H 0.199062 0.400226 0.762843 0.062 Uiso 1 1 calc R U . . .
C22 C 0.34546(5) 0.23351(16) 0.61214(9) 0.0512(4) Uani 1 1 d . . . . .
H22 H 0.326690 0.174133 0.580898 0.061 Uiso 1 1 calc R U . . .
C24 C 0.39331(5) 0.26150(16) 0.71784(9) 0.0506(4) Uani 1 1 d . . . . .
H24 H 0.407713 0.222383 0.760783 0.061 Uiso 1 1 calc R U . . .
C17 C 0.42978(5) 1.04593(18) 0.47030(8) 0.0517(4) Uani 1 1 d . . . . .
H17 H 0.450081 1.112856 0.451892 0.062 Uiso 1 1 calc R U . . .
C15 C 0.35919(5) 0.93405(19) 0.46278(9) 0.0531(4) Uani 1 1 d . . . . .
H15 H 0.330971 0.923695 0.438786 0.064 Uiso 1 1 calc R U . . .
C26 C 0.35016(6) 0.48943(18) 0.47112(9) 0.0520(4) Uani 1 1 d . . . . .
C29 C 0.26162(6) 0.55109(19) 0.47355(8) 0.0544(4) Uani 1 1 d . . . . .
H29 H 0.231428 0.572144 0.473970 0.065 Uiso 1 1 calc R U . . .
C36 C 0.24619(6) 0.52359(19) 0.72118(9) 0.0561(4) Uani 1 1 d . . . . .
H36 H 0.251992 0.585038 0.762421 0.067 Uiso 1 1 calc R U . . .
C23 C 0.36643(5) 0.17234(17) 0.67283(10) 0.0585(4) Uani 1 1 d . . . . .
H23 H 0.362571 0.069941 0.683886 0.070 Uiso 1 1 calc R U . . .
C16 C 0.38847(5) 1.0323(2) 0.43643(9) 0.0564(4) Uani 1 1 d . . . . .
H16 H 0.380224 1.090649 0.394961 0.068 Uiso 1 1 calc R U . . .
C9 C 0.45001(6) 0.91864(17) 0.78394(9) 0.0579(4) Uani 1 1 d . . . . .
H9A H 0.420956 0.953402 0.794021 0.087 Uiso 1 1 calc R U . . .
H9B H 0.456586 0.952788 0.735977 0.087 Uiso 1 1 calc R U . . .
H9C H 0.471661 0.959014 0.820210 0.087 Uiso 1 1 calc R U . . .
C27 C 0.32659(7) 0.5530(2) 0.41207(9) 0.0614(4) Uani 1 1 d . . . . .
H27 H 0.340946 0.575302 0.370046 0.074 Uiso 1 1 calc R U . . .
C28 C 0.28296(7) 0.5841(2) 0.41314(8) 0.0621(5) Uani 1 1 d . . . . .
H28 H 0.267547 0.628379 0.372337 0.074 Uiso 1 1 calc R U . . .
C31 C 0.39818(6) 0.4604(3) 0.46956(11) 0.0733(5) Uani 1 1 d . . . . .
H31A H 0.414300 0.523233 0.505600 0.110 Uiso 1 1 calc R U . . .
H31B H 0.407290 0.484034 0.421592 0.110 Uiso 1 1 calc R U . . .
H31C H 0.404231 0.355137 0.480485 0.110 Uiso 1 1 calc R U . . .
C8 C 0.50331(7) 0.3232(2) 0.90230(13) 0.0856(7) Uani 1 1 d . . . . .
H8A H 0.511326 0.277511 0.857376 0.128 Uiso 1 1 calc R U . . .
H8B H 0.474408 0.288031 0.912976 0.128 Uiso 1 1 calc R U . . .
H8C H 0.524687 0.295215 0.941803 0.128 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'
O O 0.0492 0.0322 '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
C10 N12 H12 117.1 . . ?
C10 N12 C13 125.75(11) . . ?
C13 N12 H12 117.1 . . ?
C2 O7 C8 116.74(13) . . ?
C21 N20 C19 118.48(11) . . ?
C2 N3 C4 116.59(12) . . ?
C6 N1 C2 115.09(12) . . ?
O11 C10 N12 124.99(12) . . ?
O11 C10 C5 122.30(12) . . ?
N12 C10 C5 112.27(11) . . ?
C4 C5 C10 125.31(12) . . ?
C4 C5 C6 116.96(12) . . ?
C6 C5 C10 117.73(11) . . ?
C18 C13 N12 118.28(12) . . ?
C14 C13 N12 121.74(12) . . ?
C14 C13 C18 119.98(12) . . ?
N3 C4 C5 120.93(12) . . ?
N3 C4 C19 116.28(11) . . ?
C5 C4 C19 122.78(12) . . ?
N20 C19 C4 116.22(11) . . ?
N20 C19 C24 122.77(13) . . ?
C24 C19 C4 120.98(13) . . ?
N20 C21 C25 117.22(12) . . ?
N20 C21 C22 121.91(13) . . ?
C22 C21 C25 120.87(13) . . ?
C33 C32 C30 121.45(12) . . ?
C37 C32 C30 120.25(12) . . ?
C37 C32 C33 118.30(13) . . ?
N3 C2 O7 119.87(13) . . ?
N3 C2 N1 127.99(13) . . ?
N1 C2 O7 112.14(13) . . ?
N1 C6 C5 122.29(13) . . ?
N1 C6 C9 117.07(13) . . ?
C5 C6 C9 120.63(13) . . ?
C30 C25 C21 118.94(12) . . ?
C30 C25 C26 120.39(14) . . ?
C26 C25 C21 120.67(13) . . ?
C13 C18 H18 120.0 . . ?
C17 C18 C13 120.10(13) . . ?
C17 C18 H18 120.0 . . ?
C25 C30 C32 121.33(12) . . ?
C29 C30 C32 119.60(13) . . ?
C29 C30 C25 119.04(14) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 C32 120.82(14) . . ?
C34 C33 H33 119.6 . . ?
C32 C37 H37 119.8 . . ?
C36 C37 C32 120.49(14) . . ?
C36 C37 H37 119.8 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.48(14) . . ?
C15 C14 H14 120.3 . . ?
C33 C34 H34 119.9 . . ?
C35 C34 C33 120.22(14) . . ?
C35 C34 H34 119.9 . . ?
C34 C35 H35 120.2 . . ?
C34 C35 C36 119.60(15) . . ?
C36 C35 H35 120.2 . . ?
C21 C22 H22 120.3 . . ?
C23 C22 C21 119.36(14) . . ?
C23 C22 H22 120.3 . . ?
C19 C24 H24 120.9 . . ?
C23 C24 C19 118.22(14) . . ?
C23 C24 H24 120.9 . . ?
C18 C17 H17 120.1 . . ?
C16 C17 C18 119.89(14) . . ?
C16 C17 H17 120.1 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.54(14) . . ?
C16 C15 H15 119.7 . . ?
C25 C26 C31 120.89(15) . . ?
C27 C26 C25 118.55(15) . . ?
C27 C26 C31 120.55(15) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 C30 120.66(16) . . ?
C28 C29 H29 119.7 . . ?
C37 C36 H36 119.7 . . ?
C35 C36 C37 120.54(15) . . ?
C35 C36 H36 119.7 . . ?
C22 C23 C24 119.23(14) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 C17 120.00(14) . . ?
C15 C16 H16 120.0 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C26 C27 H27 119.3 . . ?
C28 C27 C26 121.45(16) . . ?
C28 C27 H27 119.3 . . ?
C29 C28 H28 120.0 . . ?
C27 C28 C29 119.90(15) . . ?
C27 C28 H28 120.0 . . ?
C26 C31 H31A 109.5 . . ?
C26 C31 H31B 109.5 . . ?
C26 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O7 C8 H8A 109.5 . . ?
O7 C8 H8B 109.5 . . ?
O7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
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
O11 C10 1.2207(16) . ?
N12 H12 0.8800 . ?
N12 C10 1.3539(17) . ?
N12 C13 1.4150(17) . ?
O7 C2 1.3413(17) . ?
O7 C8 1.438(2) . ?
N20 C19 1.3391(17) . ?
N20 C21 1.3367(17) . ?
N3 C4 1.3483(17) . ?
N3 C2 1.3138(19) . ?
N1 C2 1.3392(19) . ?
N1 C6 1.3353(18) . ?
C10 C5 1.5075(18) . ?
C5 C4 1.3904(18) . ?
C5 C6 1.3993(19) . ?
C13 C18 1.3870(19) . ?
C13 C14 1.385(2) . ?
C4 C19 1.4868(19) . ?
C19 C24 1.388(2) . ?
C21 C25 1.496(2) . ?
C21 C22 1.390(2) . ?
C32 C30 1.492(2) . ?
C32 C33 1.390(2) . ?
C32 C37 1.388(2) . ?
C6 C9 1.505(2) . ?
C25 C30 1.400(2) . ?
C25 C26 1.404(2) . ?
C18 H18 0.9500 . ?
C18 C17 1.383(2) . ?
C30 C29 1.396(2) . ?
C33 H33 0.9500 . ?
C33 C34 1.384(2) . ?
C37 H37 0.9500 . ?
C37 C36 1.383(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(2) . ?
C34 H34 0.9500 . ?
C34 C35 1.373(2) . ?
C35 H35 0.9500 . ?
C35 C36 1.376(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.371(2) . ?
C24 H24 0.9500 . ?
C24 C23 1.384(2) . ?
C17 H17 0.9500 . ?
C17 C16 1.381(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.379(2) . ?
C26 C27 1.390(2) . ?
C26 C31 1.505(3) . ?
C29 H29 0.9500 . ?
C29 C28 1.379(2) . ?
C36 H36 0.9500 . ?
C23 H23 0.9500 . ?
C16 H16 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C27 H27 0.9500 . ?
C27 C28 1.375(3) . ?
C28 H28 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
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
O11 C10 C5 C4 90.47(17) . . . . ?
O11 C10 C5 C6 -89.37(16) . . . . ?
N12 C10 C5 C4 -96.80(15) . . . . ?
N12 C10 C5 C6 83.36(14) . . . . ?
N12 C13 C18 C17 179.64(13) . . . . ?
N12 C13 C14 C15 -179.11(13) . . . . ?
N20 C19 C24 C23 0.6(2) . . . . ?
N20 C21 C25 C30 -105.36(15) . . . . ?
N20 C21 C25 C26 75.24(17) . . . . ?
N20 C21 C22 C23 1.1(2) . . . . ?
N3 C4 C19 N20 -170.50(11) . . . . ?
N3 C4 C19 C24 11.40(19) . . . . ?
C10 N12 C13 C18 141.08(13) . . . . ?
C10 N12 C13 C14 -39.9(2) . . . . ?
C10 C5 C4 N3 177.17(11) . . . . ?
C10 C5 C4 C19 -4.1(2) . . . . ?
C10 C5 C6 N1 -176.14(12) . . . . ?
C10 C5 C6 C9 5.1(2) . . . . ?
C5 C4 C19 N20 10.75(18) . . . . ?
C5 C4 C19 C24 -167.35(14) . . . . ?
C13 N12 C10 O11 -3.1(2) . . . . ?
C13 N12 C10 C5 -175.60(11) . . . . ?
C13 C18 C17 C16 -0.2(2) . . . . ?
C13 C14 C15 C16 -0.8(2) . . . . ?
C4 N3 C2 O7 -177.27(12) . . . . ?
C4 N3 C2 N1 3.3(2) . . . . ?
C4 C5 C6 N1 4.00(19) . . . . ?
C4 C5 C6 C9 -174.78(13) . . . . ?
C4 C19 C24 C23 178.59(14) . . . . ?
C19 N20 C21 C25 176.99(11) . . . . ?
C19 N20 C21 C22 -1.87(19) . . . . ?
C19 C24 C23 C22 -1.4(3) . . . . ?
C21 N20 C19 C4 -177.06(11) . . . . ?
C21 N20 C19 C24 1.0(2) . . . . ?
C21 C25 C30 C32 3.52(19) . . . . ?
C21 C25 C30 C29 -178.55(13) . . . . ?
C21 C25 C26 C27 178.43(14) . . . . ?
C21 C25 C26 C31 -2.6(2) . . . . ?
C21 C22 C23 C24 0.6(3) . . . . ?
C32 C30 C29 C28 177.38(14) . . . . ?
C32 C33 C34 C35 0.7(2) . . . . ?
C32 C37 C36 C35 1.5(3) . . . . ?
C2 N3 C4 C5 -0.36(18) . . . . ?
C2 N3 C4 C19 -179.13(11) . . . . ?
C2 N1 C6 C5 -1.51(19) . . . . ?
C2 N1 C6 C9 177.31(14) . . . . ?
C6 N1 C2 O7 178.18(12) . . . . ?
C6 N1 C2 N3 -2.4(2) . . . . ?
C6 C5 C4 N3 -2.99(19) . . . . ?
C6 C5 C4 C19 175.70(12) . . . . ?
C25 C21 C22 C23 -177.73(15) . . . . ?
C25 C30 C29 C28 -0.6(2) . . . . ?
C25 C26 C27 C28 0.8(2) . . . . ?
C18 C13 C14 C15 -0.1(2) . . . . ?
C18 C17 C16 C15 -0.6(3) . . . . ?
C30 C32 C33 C34 -177.96(13) . . . . ?
C30 C32 C37 C36 176.89(14) . . . . ?
C30 C25 C26 C27 -1.0(2) . . . . ?
C30 C25 C26 C31 178.03(15) . . . . ?
C30 C29 C28 C27 0.4(3) . . . . ?
C33 C32 C30 C25 -111.51(15) . . . . ?
C33 C32 C30 C29 70.57(19) . . . . ?
C33 C32 C37 C36 -2.0(2) . . . . ?
C33 C34 C35 C36 -1.3(2) . . . . ?
C37 C32 C30 C25 69.62(18) . . . . ?
C37 C32 C30 C29 -108.30(16) . . . . ?
C37 C32 C33 C34 0.9(2) . . . . ?
C14 C13 C18 C17 0.6(2) . . . . ?
C14 C15 C16 C17 1.2(3) . . . . ?
C34 C35 C36 C37 0.2(3) . . . . ?
C22 C21 C25 C30 73.52(17) . . . . ?
C22 C21 C25 C26 -105.89(17) . . . . ?
C26 C25 C30 C32 -177.07(13) . . . . ?
C26 C25 C30 C29 0.9(2) . . . . ?
C26 C27 C28 C29 -0.6(3) . . . . ?
C31 C26 C27 C28 -178.18(17) . . . . ?
C8 O7 C2 N3 -0.4(2) . . . . ?
C8 O7 C2 N1 179.04(17) . . . . ?
