#------------------------------------------------------------------------------
#$Date: 2025-03-04 20:30:09 +0100 (Tue 04 de Mar de 2025) $
#$Revision: 298158 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/34/1573430.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_1573430
loop_
_publ_author_name
'Liu, Le'
'Song, Shuangji'
'Lee, Jiyeon'
'Rao, Yutao'
'Xu, Ling'
'Zhou, Mingbo'
'Yin, Bangshao'
'Oh, Juwon'
'Kim, Jiwon'
'Osuka, Atsuhiro'
'Song, Jianxin'
_publ_section_title
;
 Sub-m-benziporphyrin: a subcarbaporphyrinoid and its
 BIII complex with an unprecedented planar tridentate
 14π-aromatic network.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              1155
_journal_page_last               1160
_journal_paper_doi               10.1039/d4sc07199a
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C49 H40 N2, C2 H3 N'
_chemical_formula_sum            'C51 H43 N3'
_chemical_formula_weight         697.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-08-25 deposited with the CCDC.	2024-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.378(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0996(5)
_cell_length_b                   10.9016(5)
_cell_length_c                   29.2496(12)
_cell_measurement_reflns_used    3142
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      71.4870
_cell_measurement_theta_min      4.1110
_cell_volume                     3834.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0697
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00  92.00   1.00    5.00    --   34.48  57.00   0.00   68
  2  ω    103.00 129.00   1.00   20.00    --  105.88 111.00  30.00   26
  3  ω     75.00 149.00   1.00   20.00    --  105.88 178.00  60.00   74
  4  ω     68.00 172.00   1.00   20.00    --  105.88  15.00-150.00  104
  5  ω     57.00 104.00   1.00   20.00    --  105.88-111.00  30.00   47
  6  ω     45.00 132.00   1.00   20.00    --  105.88 -77.00  30.00   87
  7  ω     37.00  64.00   1.00    5.00    --   34.48 -99.00 150.00   27
  8  ω      1.00  59.00   1.00    5.00    --   34.48 -99.00  60.00   58
  9  ω     27.00  84.00   1.00    5.00    --   34.48-125.00 -60.00   57
 10  ω      9.00 103.00   1.00    5.00    --   34.48  19.00-120.00   94
 11  ω     39.00 129.00   1.00   20.00    --  105.88 -15.00-180.00   90
 12  ω     37.00 109.00   1.00   20.00    --  105.88 -94.00-180.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0250824000
_diffrn_orient_matrix_UB_12      0.0827052000
_diffrn_orient_matrix_UB_13      0.0425954000
_diffrn_orient_matrix_UB_21      0.0185088000
_diffrn_orient_matrix_UB_22      0.1097523000
_diffrn_orient_matrix_UB_23      -0.0314514000
_diffrn_orient_matrix_UB_31      -0.1242642000
_diffrn_orient_matrix_UB_32      0.0329847000
_diffrn_orient_matrix_UB_33      -0.0021473000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0884
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            13633
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.597
_diffrn_reflns_theta_max         66.597
_diffrn_reflns_theta_min         3.040
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.535
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_description       block
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     494
_refine_ls_number_reflns         6772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0575
_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)+(0.0454P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1414
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4736
_reflns_number_total             6772
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc07199a2.cif
_cod_data_source_block           exp_3719
_cod_depositor_comments
'Adding full bibliography for 1573430--1573435.cif.'
_cod_database_code               1573430
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C100 H10 N5'
_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   0.948
_shelx_estimated_absorpt_t_min   0.856
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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:
 N2(H2), C48(H48), C43(H43), C4(H4), C3(H3), C29(H29), C12(H12), C16(H16),
 C31(H31), C45(H45), C15(H15), C41(H41), C38(H38), C47(H47), C46(H46), C39(H39),
  C20(H20), C40(H40), C22(H22), C8(H8), C10(H10), C9(H9)
2.b Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C34(H34A,H34B,H34C), C25(H25A,H25B,H25C), C24(H24A,H24B,
 H24C), C33(H33A,H33B,H33C), C26(H26A,H26B,H26C), C51(H51A,H51B,H51C)
;
_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 1.480
_oxdiff_exptl_absorpt_empirical_full_min 0.670
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.79091(15) 0.6757(2) 0.41684(7) 0.0216(4) Uani 1 1 d . . . . .
N2 N 0.65531(15) 0.8365(2) 0.39688(7) 0.0214(4) Uani 1 1 d . . . . .
H2 H 0.705745 0.796772 0.383197 0.026 Uiso 1 1 calc R . . . .
C7 C 0.57416(18) 0.7122(2) 0.31766(8) 0.0220(5) Uani 1 1 d . . . . .
C36 C 0.76974(17) 0.8779(2) 0.52053(8) 0.0199(5) Uani 1 1 d . . . . .
N3 N 0.5249(2) 0.5951(3) 0.45262(9) 0.0422(6) Uani 1 1 d . . . . .
C44 C 0.75650(18) 0.8697(2) 0.60408(8) 0.0215(5) Uani 1 1 d . . . . .
C1 C 0.75250(18) 0.8240(2) 0.47347(8) 0.0212(5) Uani 1 1 d . . . . .
C42 C 0.83072(18) 1.0524(2) 0.57071(9) 0.0224(5) Uani 1 1 d . . . . .
C17 C 0.80396(18) 0.7147(2) 0.46086(8) 0.0213(5) Uani 1 1 d . . . . .
C37 C 0.81815(18) 0.9957(2) 0.52636(9) 0.0220(5) Uani 1 1 d . . . . .
C48 C 0.68376(18) 0.6979(2) 0.55583(9) 0.0228(5) Uani 1 1 d . . . . .
H48 H 0.666598 0.661372 0.526405 0.027 Uiso 1 1 calc R . . . .
C30 C 0.8641(2) 0.1028(3) 0.36249(8) 0.0247(5) Uani 1 1 d . . . . .
C28 C 0.72734(19) 0.2629(2) 0.37000(8) 0.0234(5) Uani 1 1 d . . . . .
C27 C 0.81096(19) 0.3541(2) 0.37083(8) 0.0229(5) Uani 1 1 d . . . . .
C14 C 0.81383(18) 0.5509(2) 0.41413(8) 0.0213(5) Uani 1 1 d . . . . .
C2 C 0.66912(18) 0.8762(2) 0.44028(8) 0.0213(5) Uani 1 1 d . . . . .
C6 C 0.50636(19) 0.8113(2) 0.33658(8) 0.0221(5) Uani 1 1 d . . . . .
C43 C 0.80067(18) 0.9881(2) 0.60863(9) 0.0228(5) Uani 1 1 d . . . . .
H43 H 0.810407 1.025476 0.638143 0.027 Uiso 1 1 calc R . . . .
C18 C 0.39346(19) 0.8427(2) 0.31271(8) 0.0235(5) Uani 1 1 d . . . . .
C5 C 0.54986(18) 0.8669(2) 0.37644(9) 0.0216(5) Uani 1 1 d . . . . .
C49 C 0.73746(17) 0.8145(2) 0.55931(8) 0.0212(5) Uani 1 1 d . . . . .
C4 C 0.50176(19) 0.9494(2) 0.40856(9) 0.0231(5) Uani 1 1 d . . . . .
H4 H 0.432476 0.990902 0.403280 0.028 Uiso 1 1 calc R . . . .
C3 C 0.57499(19) 0.9554(2) 0.44735(9) 0.0232(5) Uani 1 1 d . . . . .
H3 H 0.566479 1.002370 0.474093 0.028 Uiso 1 1 calc R . . . .
C29 C 0.75495(19) 0.1410(2) 0.36609(8) 0.0237(5) Uani 1 1 d . . . . .
H29 H 0.698036 0.080906 0.365818 0.028 Uiso 1 1 calc R . . . .
C12 C 0.62263(18) 0.6231(2) 0.34763(8) 0.0214(5) Uani 1 1 d . . . . .
H12 H 0.594672 0.612033 0.376444 0.026 Uiso 1 1 calc R . . . .
C11 C 0.71114(19) 0.5492(2) 0.33692(9) 0.0242(5) Uani 1 1 d . . . . .
C16 C 0.85769(18) 0.6131(2) 0.48830(8) 0.0234(5) Uani 1 1 d . . . . .
H16 H 0.883923 0.615950 0.520119 0.028 Uiso 1 1 calc R . . . .
C31 C 0.94512(19) 0.1933(3) 0.36256(9) 0.0281(6) Uani 1 1 d . . . . .
H31 H 1.019553 0.169592 0.359604 0.034 Uiso 1 1 calc R . . . .
C45 C 0.72841(18) 0.8025(3) 0.64317(9) 0.0246(5) Uani 1 1 d . . . . .
H45 H 0.743270 0.837414 0.672982 0.030 Uiso 1 1 calc R . . . .
C13 C 0.78096(18) 0.4850(2) 0.37510(9) 0.0234(5) Uani 1 1 d . . . . .
C15 C 0.86307(18) 0.5149(2) 0.46007(9) 0.0243(5) Uani 1 1 d . . . . .
H15 H 0.893390 0.436777 0.468644 0.029 Uiso 1 1 calc R . . . .
C23 C 0.3773(2) 0.9469(3) 0.28524(9) 0.0254(5) Uani 1 1 d . . . . .
C41 C 0.87706(19) 1.1732(2) 0.57564(9) 0.0263(5) Uani 1 1 d . . . . .
H41 H 0.883219 1.211976 0.604897 0.032 Uiso 1 1 calc R . . . .
C38 C 0.85765(19) 1.0619(2) 0.48900(9) 0.0248(5) Uani 1 1 d . . . . .
H38 H 0.851552 1.025538 0.459302 0.030 Uiso 1 1 calc R . . . .
C21 C 0.1804(2) 0.8955(3) 0.26888(9) 0.0286(6) Uani 1 1 d . . . . .
C47 C 0.65653(19) 0.6377(2) 0.59399(9) 0.0261(5) Uani 1 1 d . . . . .
H47 H 0.620910 0.559998 0.590817 0.031 Uiso 1 1 calc R . . . .
C46 C 0.68111(19) 0.6904(2) 0.63842(9) 0.0253(5) Uani 1 1 d . . . . .
H46 H 0.664204 0.646591 0.664850 0.030 Uiso 1 1 calc R . . . .
C39 C 0.9035(2) 1.1750(3) 0.49508(10) 0.0291(6) Uani 1 1 d . . . . .
H39 H 0.930045 1.216135 0.469819 0.035 Uiso 1 1 calc R . . . .
C19 C 0.3039(2) 0.7640(2) 0.31862(9) 0.0248(5) Uani 1 1 d . . . . .
C20 C 0.1988(2) 0.7922(3) 0.29635(9) 0.0266(5) Uani 1 1 d . . . . .
H20 H 0.138207 0.739172 0.300148 0.032 Uiso 1 1 calc R . . . .
C40 C 0.9123(2) 1.2333(3) 0.53934(10) 0.0289(6) Uani 1 1 d . . . . .
H40 H 0.942669 1.313481 0.543186 0.035 Uiso 1 1 calc R . . . .
C32 C 0.9209(2) 0.3179(3) 0.36681(9) 0.0267(5) Uani 1 1 d . . . . .
C22 C 0.2703(2) 0.9714(3) 0.26345(9) 0.0280(6) Uani 1 1 d . . . . .
H22 H 0.259024 1.041986 0.244450 0.034 Uiso 1 1 calc R . . . .
C8 C 0.6027(2) 0.7133(3) 0.27279(9) 0.0284(6) Uani 1 1 d . . . . .
H8 H 0.567759 0.769541 0.250960 0.034 Uiso 1 1 calc R . . . .
C35 C 0.8912(2) -0.0304(3) 0.35698(10) 0.0322(6) Uani 1 1 d . . . . .
H35A H 0.892949 -0.071776 0.386786 0.048 Uiso 1 1 calc GR . . . .
H35B H 0.964029 -0.037940 0.345548 0.048 Uiso 1 1 calc GR . . . .
H35C H 0.834306 -0.068334 0.334993 0.048 Uiso 1 1 calc GR . . . .
C10 C 0.7383(2) 0.5524(3) 0.29176(9) 0.0298(6) Uani 1 1 d . . . . .
H10 H 0.794974 0.500178 0.282848 0.036 Uiso 1 1 calc R . . . .
C34 C 0.60803(19) 0.2991(3) 0.37313(10) 0.0295(6) Uani 1 1 d . . . . .
H34A H 0.605222 0.360485 0.397453 0.044 Uiso 1 1 calc GR . . . .
H34B H 0.565246 0.226633 0.380299 0.044 Uiso 1 1 calc GR . . . .
H34C H 0.576143 0.333764 0.343663 0.044 Uiso 1 1 calc GR . . . .
C9 C 0.6830(2) 0.6314(3) 0.25988(9) 0.0317(6) Uani 1 1 d . . . . .
H9 H 0.699710 0.630085 0.228904 0.038 Uiso 1 1 calc R . . . .
C50 C 0.4624(2) 0.6429(3) 0.47286(10) 0.0337(6) Uani 1 1 d . . . . .
C25 C 0.3183(2) 0.6543(3) 0.34996(9) 0.0300(6) Uani 1 1 d . . . . .
H25A H 0.376699 0.601091 0.340322 0.045 Uiso 1 1 calc GR . . . .
H25B H 0.248171 0.608637 0.348333 0.045 Uiso 1 1 calc GR . . . .
H25C H 0.339260 0.681787 0.381637 0.045 Uiso 1 1 calc GR . . . .
C24 C 0.4708(2) 1.0347(3) 0.27891(10) 0.0337(6) Uani 1 1 d . . . . .
H24A H 0.476673 1.095697 0.303694 0.051 Uiso 1 1 calc GR . . . .
H24B H 0.455626 1.076375 0.249184 0.051 Uiso 1 1 calc GR . . . .
H24C H 0.540856 0.989227 0.279762 0.051 Uiso 1 1 calc GR . . . .
C33 C 1.0136(2) 0.4112(3) 0.36603(11) 0.0366(7) Uani 1 1 d . . . . .
H33A H 0.988473 0.478683 0.345303 0.055 Uiso 1 1 calc GR . . . .
H33B H 1.078681 0.371844 0.355153 0.055 Uiso 1 1 calc GR . . . .
H33C H 1.033668 0.443386 0.397131 0.055 Uiso 1 1 calc GR . . . .
C26 C 0.0642(2) 0.9274(3) 0.24757(10) 0.0377(7) Uani 1 1 d . . . . .
H26A H 0.022343 0.851833 0.239883 0.057 Uiso 1 1 calc GR . . . .
H26B H 0.068575 0.975598 0.219547 0.057 Uiso 1 1 calc GR . . . .
H26C H 0.026368 0.975509 0.269496 0.057 Uiso 1 1 calc GR . . . .
C51 C 0.3828(3) 0.7035(4) 0.49912(12) 0.0519(9) Uani 1 1 d . . . . .
H51A H 0.334981 0.757645 0.478768 0.078 Uiso 1 1 calc GR . . . .
H51B H 0.422777 0.752035 0.523868 0.078 Uiso 1 1 calc GR . . . .
H51C H 0.336958 0.641670 0.512391 0.078 Uiso 1 1 calc GR . . . .
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
C17 N1 C14 111.1(2) . . ?
C2 N2 H2 124.9 . . ?
C2 N2 C5 110.1(2) . . ?
C5 N2 H2 124.9 . . ?
C12 C7 C6 118.6(2) . . ?
C12 C7 C8 117.9(2) . . ?
C8 C7 C6 123.0(2) . . ?
C37 C36 C1 118.9(2) . . ?
C37 C36 C49 119.5(2) . . ?
C49 C36 C1 121.6(2) . . ?
C43 C44 C49 119.6(2) . . ?
C43 C44 C45 121.3(2) . . ?
C45 C44 C49 119.1(2) . . ?
C17 C1 C36 123.6(2) . . ?
C17 C1 C2 117.0(2) . . ?
C2 C1 C36 118.9(2) . . ?
C37 C42 C41 119.3(2) . . ?
C43 C42 C37 119.6(2) . . ?
C43 C42 C41 121.1(2) . . ?
N1 C17 C1 120.5(2) . . ?
N1 C17 C16 106.3(2) . . ?
C1 C17 C16 132.2(2) . . ?
C36 C37 C42 120.2(2) . . ?
C36 C37 C38 122.2(2) . . ?
C42 C37 C38 117.6(2) . . ?
C49 C48 H48 119.4 . . ?
C47 C48 H48 119.4 . . ?
C47 C48 C49 121.3(2) . . ?
C29 C30 C35 121.0(2) . . ?
C31 C30 C29 117.4(2) . . ?
C31 C30 C35 121.6(2) . . ?
C27 C28 C34 120.1(2) . . ?
C29 C28 C27 119.9(2) . . ?
C29 C28 C34 120.0(2) . . ?
C28 C27 C13 119.8(2) . . ?
C32 C27 C28 118.8(2) . . ?
C32 C27 C13 121.4(2) . . ?
N1 C14 C15 105.9(2) . . ?
C13 C14 N1 121.2(2) . . ?
C13 C14 C15 132.5(2) . . ?
N2 C2 C1 121.2(2) . . ?
N2 C2 C3 108.0(2) . . ?
C1 C2 C3 129.6(2) . . ?
C7 C6 C18 120.0(2) . . ?
C5 C6 C7 117.4(2) . . ?
C5 C6 C18 122.6(2) . . ?
C44 C43 H43 119.3 . . ?
C42 C43 C44 121.3(2) . . ?
C42 C43 H43 119.3 . . ?
C23 C18 C6 121.1(2) . . ?
C23 C18 C19 120.5(2) . . ?
C19 C18 C6 118.4(2) . . ?
N2 C5 C4 106.4(2) . . ?
C6 C5 N2 120.7(2) . . ?
C6 C5 C4 132.5(2) . . ?
C36 C49 C44 119.6(2) . . ?
C36 C49 C48 122.7(2) . . ?
C48 C49 C44 117.6(2) . . ?
C5 C4 H4 126.4 . . ?
C3 C4 C5 107.2(2) . . ?
C3 C4 H4 126.4 . . ?
C2 C3 H3 126.3 . . ?
C4 C3 C2 107.4(2) . . ?
C4 C3 H3 126.3 . . ?
C30 C29 H29 118.9 . . ?
C28 C29 C30 122.2(2) . . ?
C28 C29 H29 118.9 . . ?
C7 C12 H12 118.7 . . ?
C7 C12 C11 122.5(2) . . ?
C11 C12 H12 118.7 . . ?
C12 C11 C13 118.9(2) . . ?
C10 C11 C12 117.5(2) . . ?
C10 C11 C13 123.0(2) . . ?
C17 C16 H16 126.0 . . ?
C15 C16 C17 108.0(2) . . ?
C15 C16 H16 126.0 . . ?
C30 C31 H31 118.8 . . ?
C30 C31 C32 122.3(2) . . ?
C32 C31 H31 118.8 . . ?
C44 C45 H45 119.4 . . ?
C46 C45 C44 121.1(2) . . ?
C46 C45 H45 119.4 . . ?
C27 C13 C11 120.7(2) . . ?
C14 C13 C27 121.6(2) . . ?
C14 C13 C11 117.6(2) . . ?
C14 C15 H15 126.1 . . ?
C16 C15 C14 107.7(2) . . ?
C16 C15 H15 126.1 . . ?
C18 C23 C22 118.7(2) . . ?
C18 C23 C24 122.0(2) . . ?
C22 C23 C24 119.3(2) . . ?
C42 C41 H41 119.4 . . ?
C40 C41 C42 121.3(2) . . ?
C40 C41 H41 119.4 . . ?
C37 C38 H38 119.2 . . ?
C39 C38 C37 121.6(3) . . ?
C39 C38 H38 119.2 . . ?
C20 C21 C22 118.2(2) . . ?
C20 C21 C26 120.5(3) . . ?
C22 C21 C26 121.2(3) . . ?
C48 C47 H47 119.8 . . ?
C48 C47 C46 120.5(2) . . ?
C46 C47 H47 119.8 . . ?
C45 C46 C47 120.2(2) . . ?
C45 C46 H46 119.9 . . ?
C47 C46 H46 119.9 . . ?
C38 C39 H39 119.7 . . ?
C38 C39 C40 120.6(3) . . ?
C40 C39 H39 119.7 . . ?
C18 C19 C25 121.4(2) . . ?
C20 C19 C18 118.8(2) . . ?
C20 C19 C25 119.8(2) . . ?
C21 C20 C19 121.9(2) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C41 C40 C39 119.6(2) . . ?
C41 C40 H40 120.2 . . ?
C39 C40 H40 120.2 . . ?
C27 C32 C33 121.4(2) . . ?
C31 C32 C27 119.4(2) . . ?
C31 C32 C33 119.2(2) . . ?
C23 C22 H22 119.0 . . ?
C21 C22 C23 121.9(3) . . ?
C21 C22 H22 119.0 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.0(2) . . ?
C9 C8 H8 120.0 . . ?
C30 C35 H35A 109.5 . . ?
C30 C35 H35B 109.5 . . ?
C30 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C11 C10 H10 119.8 . . ?
C9 C10 C11 120.3(2) . . ?
C9 C10 H10 119.8 . . ?
C28 C34 H34A 109.5 . . ?
C28 C34 H34B 109.5 . . ?
C28 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
N3 C50 C51 179.5(3) . . ?
C19 C25 H25A 109.5 . . ?
C19 C25 H25B 109.5 . . ?
C19 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C21 C26 H26A 109.5 . . ?
C21 C26 H26B 109.5 . . ?
C21 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 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
N1 C17 1.349(3) . ?
N1 C14 1.392(3) . ?
N2 H2 0.8800 . ?
N2 C2 1.334(3) . ?
N2 C5 1.388(3) . ?
C7 C6 1.499(3) . ?
C7 C12 1.393(3) . ?
C7 C8 1.394(4) . ?
C36 C1 1.490(3) . ?
C36 C37 1.414(3) . ?
C36 C49 1.420(3) . ?
N3 C50 1.137(4) . ?
C44 C43 1.398(4) . ?
C44 C49 1.436(4) . ?
C44 C45 1.430(4) . ?
C1 C17 1.412(4) . ?
C1 C2 1.438(3) . ?
C42 C37 1.430(4) . ?
C42 C43 1.394(4) . ?
C42 C41 1.432(4) . ?
C17 C16 1.476(3) . ?
C37 C38 1.435(4) . ?
C48 H48 0.9500 . ?
C48 C49 1.426(3) . ?
C48 C47 1.367(4) . ?
C30 C29 1.400(3) . ?
C30 C31 1.390(4) . ?
C30 C35 1.501(4) . ?
C28 C27 1.417(4) . ?
C28 C29 1.377(4) . ?
C28 C34 1.509(3) . ?
C27 C13 1.482(4) . ?
C27 C32 1.405(3) . ?
C14 C13 1.370(4) . ?
C14 C15 1.462(3) . ?
C2 C3 1.462(3) . ?
C6 C18 1.503(3) . ?
C6 C5 1.367(4) . ?
C43 H43 0.9500 . ?
C18 C23 1.392(4) . ?
C18 C19 1.408(4) . ?
C5 C4 1.467(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.361(3) . ?
C3 H3 0.9500 . ?
C29 H29 0.9500 . ?
C12 H12 0.9500 . ?
C12 C11 1.403(3) . ?
C11 C13 1.497(3) . ?
C11 C10 1.397(4) . ?
C16 H16 0.9500 . ?
C16 C15 1.358(4) . ?
C31 H31 0.9500 . ?
C31 C32 1.398(4) . ?
C45 H45 0.9500 . ?
C45 C46 1.350(4) . ?
C15 H15 0.9500 . ?
C23 C22 1.404(3) . ?
C23 C24 1.510(4) . ?
C41 H41 0.9500 . ?
C41 C40 1.356(4) . ?
C38 H38 0.9500 . ?
C38 C39 1.357(4) . ?
C21 C20 1.386(4) . ?
C21 C22 1.390(4) . ?
C21 C26 1.514(3) . ?
C47 H47 0.9500 . ?
C47 C46 1.422(4) . ?
C46 H46 0.9500 . ?
C39 H39 0.9500 . ?
C39 C40 1.435(4) . ?
C19 C20 1.397(3) . ?
C19 C25 1.505(4) . ?
C20 H20 0.9500 . ?
C40 H40 0.9500 . ?
C32 C33 1.517(4) . ?
C22 H22 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.402(4) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C10 H10 0.9500 . ?
C10 C9 1.386(4) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C9 H9 0.9500 . ?
C50 C51 1.456(4) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
