#------------------------------------------------------------------------------
#$Date: 2024-09-06 03:47:35 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294563 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/66/7716611.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_7716611
loop_
_publ_author_name
'Solea, Atena B.'
'Demirci, Gozde'
'Harvey, Freya M.'
'Crochet, Aurelien'
'Zobi, Fabio'
'Mamula Steiner, Olimpia'
_publ_section_title
;
 The role of stereochemistry in the anticancer activity of Re(I)
 tricarbonyl complexes.
;
_journal_issue                   33
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              13743
_journal_page_last               13755
_journal_paper_doi               10.1039/d4dt01643b
_journal_volume                  53
_journal_year                    2024
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C34 H34 N4'
_chemical_formula_sum            'C34 H34 N4'
_chemical_formula_weight         498.65
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-18
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-06-27 deposited with the CCDC.	2024-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.364(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.2640(9)
_cell_length_b                   6.1542(3)
_cell_length_c                   15.5298(10)
_cell_measurement_reflns_used    24622
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      67.72
_cell_measurement_theta_min      5.79
_cell_volume                     1341.02(14)
_computing_cell_refinement
;
X-Area Recipe 2.0.1 (STOE, 2023)
;
_computing_data_collection
;
X-Area WinXpose 2.0.29.0 (STOE, 2023)
;
_computing_data_reduction
;
X-Area Integrate 2.5.15.0 (STOE, 2023)
X-Area LANA 2.7.12 (STOE, 2023)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 2.3, Darmstadt 2023
;
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
 810 frames, detector distance = 40 mm
;
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2, 0.6 mm diameter'
_diffrn_radiation_monochromator  'multilayer optic'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18027
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         67.920
_diffrn_reflns_theta_min         2.893
_diffrn_source                   'Genix-Cu, 3D'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.562
_exptl_absorpt_correction_T_max  0.9670
_exptl_absorpt_correction_T_min  0.8266
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270. Afterwards scaling of
reflection intensities was performed within STOE LANA. J. Koziskova, F. Hahn,
J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136-140.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             532
_exptl_crystal_recrystallization_method 'mounted on loop with oil'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
;
 Flack x determined using 1540 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_coef       0.013(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         4606
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0703
_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)+(0.1065P)²+2.5021P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1738
_refine_ls_wR_factor_ref         0.2388
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_full    0.918
_reflns_Friedel_fraction_max     0.913
_reflns_number_gt                3815
_reflns_number_total             4606
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt01643b2.cif
_cod_data_source_block           (-)-meta-l
_cod_depositor_comments
'Adding full bibliography for 7716611--7716619.cif.'
_cod_database_code               7716611
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.832
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C14(H14), C29(H29), C31(H31)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C15(H15A,H15B), C28(H28A,H28B), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C7(H7), C8(H8), C18(H18), C20(H20), C21(H21),
 C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C33(H33A,H33B,H33C), C34(H34A,H34B,
 H34C)
;
_olex2_exptl_crystal_mounting_method
'recrystallised from a mixture of chloroform and diethylether by solvent layering'
_olex2_submission_special_instructions 'No special instructions were received'
_stoe_detector_distance          '40.0 mm'
_stoe_detector_pixelsize_x       '0.150 mm'
_stoe_detector_pixelsize_y       '0.150 mm'
_stoe_detector_size_x            '34.0 cm'
_stoe_detector_size_y            '34.0 cm'
_stoe_evaluation_integration_a   9.0
_stoe_evaluation_integration_b   0.0
_stoe_evaluation_integration_ems 0.026
_stoe_evaluation_lana_bis_l_even_max -
_stoe_evaluation_lana_bis_l_odd_max -
_stoe_evaluation_lana_bos_l_even_max 4
_stoe_evaluation_lana_bos_l_odd_max 1
_stoe_evaluation_lana_completeness 97.3
_stoe_evaluation_lana_dxs_max_order 1
_stoe_evaluation_lana_dys_max_order 1
_stoe_evaluation_lana_fs_max_order 3
_stoe_evaluation_lana_max_2theta_available 135.9
_stoe_evaluation_lana_max_2theta_desired 135.9
_stoe_evaluation_lana_mean_redundancy 6.9
_stoe_evaluation_lana_number_refls_after_or 18033
_stoe_evaluation_lana_number_refls_outliers 7323
_stoe_evaluation_lana_number_refls_total 25356
_stoe_evaluation_lana_number_refls_unique 2611
_stoe_evaluation_lana_number_refls_written 18033
_stoe_evaluation_lana_or_c1      0.035
_stoe_evaluation_lana_or_c2      0
_stoe_evaluation_lana_or_c3      0
_stoe_evaluation_lana_or_c4      0.7
_stoe_evaluation_lana_point_group 2/m
_stoe_evaluation_lana_table
;
#----------------------------------------------------------------------------
2Theta          12.4   27.0   41.6   56.2   70.8   85.4  100.0  114.6  129.2
#----------------------------------------------------------------------------
<Resolution>    5.46   3.12   2.13   1.63   1.33   1.14   1.01   0.92   0.86
N(total)         194    990   2208   3073   4390   4854   4428   3398   1821
<Redundancy>     4.5    8.5    9.4    8.3    8.7    7.9    6.7    5.2    4.0
Complet. [%%]    84.6   98.7  100.0  100.0  100.0  100.0  100.0  100.0   83.9
<I/sigma>      266.6  277.1  182.3   80.3   44.3   38.3   19.6   10.0    1.8
R(int)         0.027  0.023  0.023  0.035  0.043  0.041  0.046  0.104  0.377
#----------------------------------------------------------------------------
;
_stoe_measurement_identifier     (-)-Meta-L
_stoe_measurement_max_exposure_per_frame '60.0 s'
_stoe_measurement_mean_exposure_per_frame '60.0 s'
_stoe_measurement_min_exposure_per_frame '60.0 s'
_stoe_measurement_total_exposure_time '13.5 h'
_stoe_measurement_total_frame_number 810
_stoe_measurement_total_run_number 9
_stoe_measurement_tube_power     '30.0 W'
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 0.3777(4) 0.8419(9) 0.1798(4) 0.0341(12) Uani 1 1 d . . . . .
N2 N 0.6050(3) 0.6500(8) 0.1403(3) 0.0278(11) Uani 1 1 d . . . . .
N3 N 0.1273(4) 0.2170(10) 0.3479(4) 0.0427(14) Uani 1 1 d . . . . .
N4 N -0.1215(4) 0.3373(9) 0.3405(3) 0.0318(12) Uani 1 1 d . . . . .
C1 C 0.3003(5) 0.7635(11) 0.2094(4) 0.0357(15) Uani 1 1 d . . . . .
H1 H 0.250730 0.862950 0.214697 0.043 Uiso 1 1 calc R U . . .
C2 C 0.2884(4) 0.5492(10) 0.2325(4) 0.0293(13) Uani 1 1 d . . . . .
C3 C 0.3632(4) 0.4085(11) 0.2257(4) 0.0320(14) Uani 1 1 d . . . . .
H3 H 0.359185 0.259359 0.240346 0.038 Uiso 1 1 calc R U . . .
C4 C 0.4436(4) 0.4873(11) 0.1973(4) 0.0320(14) Uani 1 1 d . . . . .
H4 H 0.495793 0.393150 0.194548 0.038 Uiso 1 1 calc R U . . .
C5 C 0.4479(4) 0.7024(10) 0.1732(4) 0.0256(13) Uani 1 1 d . . . . .
C6 C 0.5283(4) 0.7862(10) 0.1347(4) 0.0262(13) Uani 1 1 d . . . . .
C7 C 0.5258(4) 0.9864(10) 0.0932(4) 0.0284(13) Uani 1 1 d . . . . .
H7 H 0.472745 1.080288 0.092297 0.034 Uiso 1 1 calc R U . . .
C8 C 0.6008(4) 1.0491(11) 0.0531(4) 0.0308(13) Uani 1 1 d . . . . .
H8 H 0.599973 1.185697 0.024471 0.037 Uiso 1 1 calc R U . . .
C9 C 0.6774(4) 0.9075(10) 0.0556(4) 0.0268(13) Uani 1 1 d . . . . .
C10 C 0.6778(4) 0.7133(10) 0.1014(4) 0.0290(13) Uani 1 1 d . . . . .
C11 C 0.7640(4) 0.5695(10) 0.1094(4) 0.0327(14) Uani 1 1 d . . . . .
H11A H 0.744237 0.422411 0.087554 0.039 Uiso 1 1 calc R U . . .
H11B H 0.794002 0.556671 0.171855 0.039 Uiso 1 1 calc R U . . .
C12 C 0.8366(5) 0.6607(11) 0.0574(4) 0.0337(15) Uani 1 1 d . . . . .
H12 H 0.894376 0.568730 0.057319 0.040 Uiso 1 1 calc R U . . .
C13 C 0.8565(4) 0.9068(11) 0.0789(4) 0.0313(14) Uani 1 1 d . . . . .
C14 C 0.7619(4) 0.9498(11) 0.0119(4) 0.0323(14) Uani 1 1 d . . . . .
H14 H 0.759703 1.084893 -0.024218 0.039 Uiso 1 1 calc R U . . .
C15 C 0.7831(5) 0.7311(12) -0.0337(4) 0.0403(16) Uani 1 1 d . . . . .
H15A H 0.725679 0.643468 -0.056171 0.048 Uiso 1 1 calc R U . . .
H15B H 0.824205 0.747687 -0.078225 0.048 Uiso 1 1 calc R U . . .
C16 C 0.8626(5) 0.9851(12) 0.1721(4) 0.0417(16) Uani 1 1 d . . . . .
H16A H 0.920873 0.928433 0.208384 0.063 Uiso 1 1 calc R U . . .
H16B H 0.807005 0.933390 0.195122 0.063 Uiso 1 1 calc R U . . .
H16C H 0.864025 1.144337 0.173288 0.063 Uiso 1 1 calc R U . . .
C17 C 0.9432(5) 0.9899(13) 0.0442(5) 0.0493(18) Uani 1 1 d . . . . .
H17A H 1.001379 0.933873 0.080740 0.074 Uiso 1 1 calc R U . . .
H17B H 0.943972 1.149076 0.045643 0.074 Uiso 1 1 calc R U . . .
H17C H 0.940031 0.940104 -0.016234 0.074 Uiso 1 1 calc R U . . .
C18 C 0.2024(5) 0.2963(12) 0.3162(5) 0.0401(16) Uani 1 1 d . . . . .
H18 H 0.261429 0.222204 0.331860 0.048 Uiso 1 1 calc R U . . .
C19 C 0.2006(4) 0.4765(10) 0.2628(4) 0.0291(13) Uani 1 1 d . . . . .
C20 C 0.1132(5) 0.5800(13) 0.2412(5) 0.0451(18) Uani 1 1 d . . . . .
H20 H 0.106889 0.704371 0.204329 0.054 Uiso 1 1 calc R U . . .
C21 C 0.0357(5) 0.5027(13) 0.2730(5) 0.0450(18) Uani 1 1 d . . . . .
H21 H -0.023862 0.574794 0.258157 0.054 Uiso 1 1 calc R U . . .
C22 C 0.0434(4) 0.3218(11) 0.3262(4) 0.0307(14) Uani 1 1 d . . . . .
C23 C -0.0381(4) 0.2279(11) 0.3601(4) 0.0289(13) Uani 1 1 d . . . . .
C24 C -0.0298(4) 0.0367(11) 0.4071(4) 0.0360(15) Uani 1 1 d . . . . .
H24 H 0.029821 -0.035825 0.420501 0.043 Uiso 1 1 calc R U . . .
C25 C -0.1098(5) -0.0494(12) 0.4349(4) 0.0395(16) Uani 1 1 d . . . . .
H25 H -0.105364 -0.180483 0.467742 0.047 Uiso 1 1 calc R U . . .
C26 C -0.1957(4) 0.0592(11) 0.4140(4) 0.0333(14) Uani 1 1 d . . . . .
C27 C -0.1983(5) 0.2542(12) 0.3668(4) 0.0350(15) Uani 1 1 d . . . . .
C28 C -0.2922(5) 0.3725(13) 0.3451(4) 0.0415(17) Uani 1 1 d . . . . .
H28A H -0.310617 0.386545 0.280723 0.050 Uiso 1 1 calc R U . . .
H28B H -0.285041 0.520524 0.370297 0.050 Uiso 1 1 calc R U . . .
C29 C -0.3708(5) 0.2522(13) 0.3809(4) 0.0436(17) Uani 1 1 d . . . . .
H29 H -0.435427 0.320517 0.367720 0.052 Uiso 1 1 calc R U . . .
C30 C -0.3368(5) 0.1821(11) 0.4777(4) 0.0373(16) Uani 1 1 d . . . . .
C31 C -0.2880(4) -0.0140(12) 0.4387(4) 0.0379(15) Uani 1 1 d . . . . .
H31 H -0.286244 -0.154652 0.471145 0.045 Uiso 1 1 calc R U . . .
C32 C -0.3664(5) 0.0084(15) 0.3556(5) 0.052(2) Uani 1 1 d . . . . .
H32A H -0.425462 -0.074152 0.358153 0.062 Uiso 1 1 calc R U . . .
H32B H -0.343780 -0.017703 0.299861 0.062 Uiso 1 1 calc R U . . .
C33 C -0.2756(6) 0.3408(13) 0.5377(4) 0.0487(19) Uani 1 1 d . . . . .
H33A H -0.247215 0.266899 0.592045 0.073 Uiso 1 1 calc R U . . .
H33B H -0.314994 0.462168 0.551165 0.073 Uiso 1 1 calc R U . . .
H33C H -0.224811 0.396174 0.508656 0.073 Uiso 1 1 calc R U . . .
C34 C -0.4182(6) 0.1033(15) 0.5216(5) 0.053(2) Uani 1 1 d . . . . .
H34A H -0.449451 0.228520 0.543374 0.079 Uiso 1 1 calc R U . . .
H34B H -0.392852 0.007322 0.570624 0.079 Uiso 1 1 calc R U . . .
H34C H -0.464673 0.023533 0.478962 0.079 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
6 0 -1 0.3640
25 -30 24 0.1951
22 -30 -1 0.1737
19 -25 -30 0.2686
-2 30 29 0.2481
1 -1 30 0.5216
-1 -26 30 0.2674
-30 1 3 0.4158
-15 -14 -6 0.3385
-15 11 -10 0.1710
-13 15 12 0.2249
-5 -30 4 0.2012
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 C1 117.6(6) . . ?
C10 N2 C6 117.7(5) . . ?
C18 N3 C22 117.6(6) . . ?
C27 N4 C23 118.5(6) . . ?
N1 C1 H1 117.6 . . ?
N1 C1 C2 124.8(6) . . ?
C2 C1 H1 117.6 . . ?
C1 C2 C3 116.2(6) . . ?
C1 C2 C19 121.2(5) . . ?
C3 C2 C19 122.6(6) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.7(6) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(6) . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 121.7(6) . . ?
N1 C5 C6 116.9(5) . . ?
C4 C5 C6 121.3(5) . . ?
N2 C6 C5 115.5(5) . . ?
N2 C6 C7 121.8(5) . . ?
C7 C6 C5 122.7(5) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.9(5) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 120.7 . . ?
C7 C8 C9 118.6(6) . . ?
C9 C8 H8 120.7 . . ?
C8 C9 C14 124.5(5) . . ?
C10 C9 C8 118.9(5) . . ?
C10 C9 C14 116.6(5) . . ?
N2 C10 C9 123.0(5) . . ?
N2 C10 C11 118.5(5) . . ?
C9 C10 C11 118.5(5) . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C10 C11 C12 111.2(5) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C11 C12 H12 115.5 . . ?
C11 C12 C13 110.8(5) . . ?
C11 C12 C15 108.5(5) . . ?
C13 C12 H12 115.5 . . ?
C15 C12 H12 115.5 . . ?
C15 C12 C13 88.0(5) . . ?
C12 C13 C14 85.4(5) . . ?
C16 C13 C12 119.3(6) . . ?
C16 C13 C14 118.4(5) . . ?
C16 C13 C17 108.7(6) . . ?
C17 C13 C12 112.1(5) . . ?
C17 C13 C14 111.3(5) . . ?
C9 C14 C13 109.4(4) . . ?
C9 C14 H14 116.6 . . ?
C9 C14 C15 106.7(5) . . ?
C13 C14 H14 116.6 . . ?
C13 C14 C15 86.7(5) . . ?
C15 C14 H14 116.6 . . ?
C12 C15 C14 86.1(5) . . ?
C12 C15 H15A 114.3 . . ?
C12 C15 H15B 114.3 . . ?
C14 C15 H15A 114.3 . . ?
C14 C15 H15B 114.3 . . ?
H15A C15 H15B 111.4 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 H18 117.3 . . ?
N3 C18 C19 125.4(6) . . ?
C19 C18 H18 117.3 . . ?
C18 C19 C2 120.4(5) . . ?
C18 C19 C20 115.7(6) . . ?
C20 C19 C2 123.9(6) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.0(6) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 119.6 . . ?
C20 C21 C22 120.9(6) . . ?
C22 C21 H21 119.6 . . ?
N3 C22 C21 120.4(6) . . ?
N3 C22 C23 116.4(6) . . ?
C21 C22 C23 123.2(6) . . ?
N4 C23 C22 116.2(5) . . ?
N4 C23 C24 122.1(6) . . ?
C24 C23 C22 121.6(5) . . ?
C23 C24 H24 120.3 . . ?
C23 C24 C25 119.4(6) . . ?
C25 C24 H24 120.3 . . ?
C24 C25 H25 120.6 . . ?
C26 C25 C24 118.9(6) . . ?
C26 C25 H25 120.6 . . ?
C25 C26 C27 118.4(6) . . ?
C25 C26 C31 125.1(6) . . ?
C27 C26 C31 116.5(6) . . ?
N4 C27 C26 122.7(6) . . ?
N4 C27 C28 119.4(6) . . ?
C26 C27 C28 117.9(6) . . ?
C27 C28 H28A 109.3 . . ?
C27 C28 H28B 109.3 . . ?
C27 C28 C29 111.4(6) . . ?
H28A C28 H28B 108.0 . . ?
C29 C28 H28A 109.3 . . ?
C29 C28 H28B 109.3 . . ?
C28 C29 H29 115.5 . . ?
C28 C29 C30 111.4(5) . . ?
C28 C29 C32 108.0(6) . . ?
C30 C29 H29 115.5 . . ?
C30 C29 C32 87.5(6) . . ?
C32 C29 H29 115.5 . . ?
C29 C30 C31 85.6(5) . . ?
C33 C30 C29 117.4(6) . . ?
C33 C30 C31 119.2(6) . . ?
C33 C30 C34 109.3(6) . . ?
C34 C30 C29 112.9(6) . . ?
C34 C30 C31 110.7(6) . . ?
C26 C31 C30 109.7(6) . . ?
C26 C31 H31 116.4 . . ?
C26 C31 C32 107.1(5) . . ?
C30 C31 H31 116.4 . . ?
C32 C31 C30 87.1(5) . . ?
C32 C31 H31 116.4 . . ?
C29 C32 H32A 114.3 . . ?
C29 C32 H32B 114.3 . . ?
C31 C32 C29 86.0(5) . . ?
C31 C32 H32A 114.3 . . ?
C31 C32 H32B 114.3 . . ?
H32A C32 H32B 111.5 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C30 C34 H34A 109.5 . . ?
C30 C34 H34B 109.5 . . ?
C30 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 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 C1 1.358(8) . ?
N1 C5 1.337(7) . ?
N2 C6 1.369(7) . ?
N2 C10 1.349(8) . ?
N3 C18 1.348(9) . ?
N3 C22 1.349(8) . ?
N4 C23 1.353(8) . ?
N4 C27 1.337(8) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(9) . ?
C2 C3 1.392(8) . ?
C2 C19 1.485(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(9) . ?
C5 C6 1.479(8) . ?
C6 C7 1.388(9) . ?
C7 H7 0.9500 . ?
C7 C8 1.386(8) . ?
C8 H8 0.9500 . ?
C8 C9 1.392(8) . ?
C9 C10 1.390(8) . ?
C9 C14 1.509(8) . ?
C10 C11 1.502(8) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.530(8) . ?
C12 H12 1.0000 . ?
C12 C13 1.566(9) . ?
C12 C15 1.544(9) . ?
C13 C14 1.571(8) . ?
C13 C16 1.513(9) . ?
C13 C17 1.524(9) . ?
C14 H14 1.0000 . ?
C14 C15 1.574(9) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18 0.9500 . ?
C18 C19 1.382(9) . ?
C19 C20 1.386(8) . ?
C20 H20 0.9500 . ?
C20 C21 1.374(9) . ?
C21 H21 0.9500 . ?
C21 C22 1.379(9) . ?
C22 C23 1.476(8) . ?
C23 C24 1.379(9) . ?
C24 H24 0.9500 . ?
C24 C25 1.395(9) . ?
C25 H25 0.9500 . ?
C25 C26 1.381(9) . ?
C26 C27 1.404(9) . ?
C26 C31 1.505(8) . ?
C27 C28 1.508(9) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.530(9) . ?
C29 H29 1.0000 . ?
C29 C30 1.555(9) . ?
C29 C32 1.556(12) . ?
C30 C31 1.568(10) . ?
C30 C33 1.514(10) . ?
C30 C34 1.528(9) . ?
C31 H31 1.0000 . ?
C31 C32 1.555(9) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 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
N1 C1 C2 C3 1.3(10) . . . . ?
N1 C1 C2 C19 -178.9(6) . . . . ?
N1 C5 C6 N2 171.0(5) . . . . ?
N1 C5 C6 C7 -10.9(8) . . . . ?
N2 C6 C7 C8 2.5(8) . . . . ?
N2 C10 C11 C12 177.0(5) . . . . ?
N3 C18 C19 C2 179.6(7) . . . . ?
N3 C18 C19 C20 -0.2(11) . . . . ?
N3 C22 C23 N4 177.9(6) . . . . ?
N3 C22 C23 C24 -3.6(9) . . . . ?
N4 C23 C24 C25 0.7(9) . . . . ?
N4 C27 C28 C29 -179.8(6) . . . . ?
C1 N1 C5 C4 -1.5(8) . . . . ?
C1 N1 C5 C6 175.6(5) . . . . ?
C1 C2 C3 C4 0.2(9) . . . . ?
C1 C2 C19 C18 -154.7(7) . . . . ?
C1 C2 C19 C20 25.1(10) . . . . ?
C2 C3 C4 C5 -2.2(9) . . . . ?
C2 C19 C20 C21 -179.4(7) . . . . ?
C3 C2 C19 C18 25.1(9) . . . . ?
C3 C2 C19 C20 -155.1(7) . . . . ?
C3 C4 C5 N1 2.9(9) . . . . ?
C3 C4 C5 C6 -174.0(5) . . . . ?
C4 C5 C6 N2 -12.0(8) . . . . ?
C4 C5 C6 C7 166.2(5) . . . . ?
C5 N1 C1 C2 -0.7(10) . . . . ?
C5 C6 C7 C8 -175.5(5) . . . . ?
C6 N2 C10 C9 -0.8(8) . . . . ?
C6 N2 C10 C11 177.9(5) . . . . ?
C6 C7 C8 C9 0.0(8) . . . . ?
C7 C8 C9 C10 -2.7(8) . . . . ?
C7 C8 C9 C14 177.4(5) . . . . ?
C8 C9 C10 N2 3.2(9) . . . . ?
C8 C9 C10 C11 -175.5(6) . . . . ?
C8 C9 C14 C13 131.1(6) . . . . ?
C8 C9 C14 C15 -136.4(6) . . . . ?
C9 C10 C11 C12 -4.3(8) . . . . ?
C9 C14 C15 C12 -81.7(5) . . . . ?
C10 N2 C6 C5 176.0(5) . . . . ?
C10 N2 C6 C7 -2.2(8) . . . . ?
C10 C9 C14 C13 -48.7(7) . . . . ?
C10 C9 C14 C15 43.8(6) . . . . ?
C10 C11 C12 C13 49.4(7) . . . . ?
C10 C11 C12 C15 -45.6(7) . . . . ?
C11 C12 C13 C14 -81.2(5) . . . . ?
C11 C12 C13 C16 38.9(8) . . . . ?
C11 C12 C13 C17 167.6(6) . . . . ?
C11 C12 C15 C14 83.6(6) . . . . ?
C12 C13 C14 C9 79.4(5) . . . . ?
C12 C13 C14 C15 -27.2(4) . . . . ?
C13 C12 C15 C14 -27.7(5) . . . . ?
C13 C14 C15 C12 27.6(5) . . . . ?
C14 C9 C10 N2 -176.9(5) . . . . ?
C14 C9 C10 C11 4.4(8) . . . . ?
C15 C12 C13 C14 27.8(4) . . . . ?
C15 C12 C13 C16 147.9(6) . . . . ?
C15 C12 C13 C17 -83.4(6) . . . . ?
C16 C13 C14 C9 -41.6(8) . . . . ?
C16 C13 C14 C15 -148.2(6) . . . . ?
C17 C13 C14 C9 -168.6(5) . . . . ?
C17 C13 C14 C15 84.8(6) . . . . ?
C18 N3 C22 C21 0.3(10) . . . . ?
C18 N3 C22 C23 178.5(6) . . . . ?
C18 C19 C20 C21 0.5(11) . . . . ?
C19 C2 C3 C4 -179.6(5) . . . . ?
C19 C20 C21 C22 -0.3(12) . . . . ?
C20 C21 C22 N3 -0.1(11) . . . . ?
C20 C21 C22 C23 -178.1(7) . . . . ?
C21 C22 C23 N4 -3.9(9) . . . . ?
C21 C22 C23 C24 174.6(7) . . . . ?
C22 N3 C18 C19 -0.2(11) . . . . ?
C22 C23 C24 C25 -177.7(6) . . . . ?
C23 N4 C27 C26 0.4(9) . . . . ?
C23 N4 C27 C28 -179.5(6) . . . . ?
C23 C24 C25 C26 0.4(10) . . . . ?
C24 C25 C26 C27 -1.1(10) . . . . ?
C24 C25 C26 C31 179.5(6) . . . . ?
C25 C26 C27 N4 0.7(10) . . . . ?
C25 C26 C27 C28 -179.4(6) . . . . ?
C25 C26 C31 C30 132.8(7) . . . . ?
C25 C26 C31 C32 -134.1(7) . . . . ?
C26 C27 C28 C29 0.4(9) . . . . ?
C26 C31 C32 C29 -82.3(6) . . . . ?
C27 N4 C23 C22 177.4(5) . . . . ?
C27 N4 C23 C24 -1.1(9) . . . . ?
C27 C26 C31 C30 -46.6(7) . . . . ?
C27 C26 C31 C32 46.5(8) . . . . ?
C27 C28 C29 C30 46.8(8) . . . . ?
C27 C28 C29 C32 -47.7(7) . . . . ?
C28 C29 C30 C31 -81.0(7) . . . . ?
C28 C29 C30 C33 39.7(9) . . . . ?
C28 C29 C30 C34 168.4(7) . . . . ?
C28 C29 C32 C31 84.0(6) . . . . ?
C29 C30 C31 C26 79.7(6) . . . . ?
C29 C30 C31 C32 -27.5(5) . . . . ?
C30 C29 C32 C31 -27.7(5) . . . . ?
C30 C31 C32 C29 27.4(5) . . . . ?
C31 C26 C27 N4 -179.8(6) . . . . ?
C31 C26 C27 C28 0.0(9) . . . . ?
C32 C29 C30 C31 27.4(5) . . . . ?
C32 C29 C30 C33 148.1(6) . . . . ?
C32 C29 C30 C34 -83.2(7) . . . . ?
C33 C30 C31 C26 -39.4(8) . . . . ?
C33 C30 C31 C32 -146.6(6) . . . . ?
C34 C30 C31 C26 -167.5(6) . . . . ?
C34 C30 C31 C32 85.4(6) . . . . ?
