#------------------------------------------------------------------------------
#$Date: 2022-09-06 19:19:31 +0300 (Tue, 06 Sep 2022) $
#$Revision: 277688 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/75/1567589.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_1567589
loop_
_publ_author_name
'Rocco, Dalila'
'Nikoletić, Anamarija'
'Prescimone, Alessandro'
'Constable, Edwin C.'
'Housecroft, Catherine E.'
_publ_section_title
;
 To Be or Not to Be a (4,4) Net: Reactions of
 4′-{4-(N,N-Diethylaminophenyl)}- and
 4′-{4-(N,N-Diphenylaminophenyl)}-3,2′:6′,3″-
 and 4,2′:6′,4″-Terpyridines with Cobalt(II)
 Thiocyanate
;
_journal_issue                   8
_journal_name_full               Crystals
_journal_page_first              1136
_journal_paper_doi               10.3390/cryst12081136
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C33 H24 N4'
_chemical_formula_sum            'C33 H24 N4'
_chemical_formula_weight         476.56
_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             2022-04-29
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha                90
_cell_angle_beta                 146.585(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   34.855(5)
_cell_length_b                   8.6116(8)
_cell_length_c                   30.178(5)
_cell_measurement_reflns_used    10443
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.88
_cell_measurement_theta_min      4.59
_cell_volume                     4988.3(15)
_computing_cell_refinement       'X-Area Recipe 1.37.0.0 (STOE, 2021)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.175.0 (STOE, 2021)'
_computing_data_reduction
;
X-Area Integrate 2.5.1.0 (STOE, 2021)
X-Area LANA 2.6.2.0 (STOE, 2021)
;
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'EIGER2 1M'
_diffrn_detector_area_resol_mean 13.33
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
 3613 frames, detector distance = 40 mm
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  Basel-Cu-Stoe
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            36601
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         67.998
_diffrn_reflns_theta_min         4.607
_diffrn_source                   'Axo Cu'
_diffrn_source_current           1.00
_diffrn_source_power             0.050
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_correction_T_min  0.9743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens 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.
Finally a spherical absorption correction was done within STOE LANA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.08
_exptl_crystal_size_rad          0.150
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       0.0024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1376
_refine_ls_R_factor_gt           0.0975
_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)+(0.1000P)²+27.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2194
_refine_ls_wR_factor_ref         0.2699
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3249
_reflns_number_total             4524
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            NIA002_150K.cif
_cod_data_source_block           nia002_150k
_cod_original_cell_volume        4988.2(12)
_cod_database_code               1567589
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.891
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C24(H24), C14(H14), C9(H9), C23(H23), C6(H6), C13(H13), C3(H3), C10(H10),
 C12(H12), C2(H2), C26(H26), C21(H21), C25(H25), C29(H29), C27(H27), C1(H1),
 C17(H17), C30(H30), C20(H20), C33(H33), C18(H18), C19(H19), C31(H31), C32(H32)
;
_olex2_date_sample_data_collection 2022-04-28
_olex2_date_sample_submission    2022-04-22
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop in perfluoroether oil'
_olex2_submission_original_sample_id NIA002_150K
_olex2_submission_special_instructions 'No special instructions were received'
_stoe_detector_distance          '40.0 mm'
_stoe_detector_pixelsize_x       '0.075 mm'
_stoe_detector_pixelsize_y       '0.075 mm'
_stoe_detector_size_x            '8.0 cm'
_stoe_detector_size_y            '7.7 cm'
_stoe_evaluation_integration_a   5.6
_stoe_evaluation_integration_b   -1.0
_stoe_evaluation_integration_ems 0.020
_stoe_evaluation_lana_bis_l_even_max -
_stoe_evaluation_lana_bis_l_odd_max -
_stoe_evaluation_lana_bos_l_even_max -
_stoe_evaluation_lana_bos_l_odd_max -
_stoe_evaluation_lana_completeness 99.7
_stoe_evaluation_lana_dxs_max_order -
_stoe_evaluation_lana_dys_max_order -
_stoe_evaluation_lana_fs_max_order 3
_stoe_evaluation_lana_max_2theta_available 147.6
_stoe_evaluation_lana_max_2theta_desired 136.0
_stoe_evaluation_lana_mean_redundancy 8.1
_stoe_evaluation_lana_number_refls_after_or 36616
_stoe_evaluation_lana_number_refls_outliers 13279
_stoe_evaluation_lana_number_refls_total 49895
_stoe_evaluation_lana_number_refls_unique 4534
_stoe_evaluation_lana_number_refls_written 36616
_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          12.2   26.8   41.4   56.0   70.6   85.2   99.8  114.4  129.0
----------------------------------------------------------------------------
<Resolution>    6.01   3.06   2.14   1.60   1.33   1.14   1.01   0.92   0.86
N(total)          21    686   1994   4026   9475  11242   8538   7845   6068
<Redundancy>     1.3    3.8    4.9    6.4   11.3   11.0    7.7    7.4    6.8
Complet. [%%]    57.7   99.2  100.0  100.0  100.0  100.0   99.9   99.9  100.0
<I/sigma>       74.8  104.8   51.8   23.0   12.8   11.8    7.1    2.8    1.0
R(int)         0.298  0.055  0.042  0.052  0.077  0.071  0.115  0.290  0.524
----------------------------------------------------------------------------
;
_stoe_measurement_identifier     NIA002_150K
_stoe_measurement_max_exposure_per_frame '10.0 s'
_stoe_measurement_mean_exposure_per_frame '10.0 s'
_stoe_measurement_min_exposure_per_frame '10.0 s'
_stoe_measurement_total_exposure_time '10.0 h'
_stoe_measurement_total_frame_number 3613
_stoe_measurement_total_run_number 58
_stoe_measurement_tube_power     '50.0 W'
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
N2 N 0.70951(16) 0.6041(4) 0.58814(18) 0.0461(8) Uani 1 1 d . . . . .
N4 N 0.54836(18) 0.9405(4) 0.18586(19) 0.0507(8) Uani 1 1 d . . . . .
N1 N 0.7765(2) 0.1222(4) 0.5841(2) 0.0659(10) Uani 1 1 d . . . . .
C8 C 0.62627(19) 0.7792(4) 0.3847(2) 0.0448(9) Uani 1 1 d . . . . .
C4 C 0.74693(19) 0.3662(4) 0.5900(2) 0.0452(9) Uani 1 1 d . . . . .
C24 C 0.6275(2) 0.6609(5) 0.1831(3) 0.0560(10) Uani 1 1 d . . . . .
H24 H 0.668186 0.603142 0.219628 0.067 Uiso 1 1 calc R U . . .
C7 C 0.6551(2) 0.7203(5) 0.4551(2) 0.0489(9) Uani 1 1 d . . . . .
C22 C 0.55786(19) 0.8432(5) 0.1572(2) 0.0468(9) Uani 1 1 d . . . . .
C15 C 0.6803(2) 0.7462(5) 0.5582(2) 0.0464(9) Uani 1 1 d . . . . .
C14 C 0.6516(2) 0.8055(5) 0.4912(2) 0.0494(9) Uani 1 1 d . . . . .
H14 H 0.629960 0.902138 0.470556 0.059 Uiso 1 1 calc R U . . .
C9 C 0.5912(2) 0.6812(5) 0.3220(2) 0.0510(9) Uani 1 1 d . . . . .
H9 H 0.585692 0.577209 0.324218 0.061 Uiso 1 1 calc R U . . .
N3 N 0.6771(2) 0.8236(5) 0.6782(3) 0.0712(11) Uani 1 1 d . . . . .
C23 C 0.6194(2) 0.7596(5) 0.2113(2) 0.0514(9) Uani 1 1 d . . . . .
H23 H 0.655189 0.770127 0.266329 0.062 Uiso 1 1 calc R U . . .
C6 C 0.6878(2) 0.5765(4) 0.4885(2) 0.0475(9) Uani 1 1 d . . . . .
H6 H 0.692946 0.517505 0.467832 0.057 Uiso 1 1 calc R U . . .
C16 C 0.67844(19) 0.8322(4) 0.5987(2) 0.0469(9) Uani 1 1 d . . . . .
C13 C 0.6332(2) 0.9342(5) 0.3794(2) 0.0497(9) Uani 1 1 d . . . . .
H13 H 0.655285 1.002829 0.419908 0.060 Uiso 1 1 calc R U . . .
C5 C 0.71312(19) 0.5204(4) 0.5536(2) 0.0456(9) Uani 1 1 d . . . . .
C11 C 0.5731(2) 0.8884(5) 0.2521(2) 0.0473(9) Uani 1 1 d . . . . .
C3 C 0.7846(2) 0.3249(5) 0.6641(2) 0.0523(10) Uani 1 1 d . . . . .
H3 H 0.787015 0.391726 0.690678 0.063 Uiso 1 1 calc R U . . .
C10 C 0.5640(2) 0.7341(5) 0.2557(2) 0.0503(9) Uani 1 1 d . . . . .
H10 H 0.539910 0.666371 0.214009 0.060 Uiso 1 1 calc R U . . .
C12 C 0.6074(2) 0.9889(5) 0.3140(2) 0.0493(9) Uani 1 1 d . . . . .
H12 H 0.613254 1.092644 0.311948 0.059 Uiso 1 1 calc R U . . .
C2 C 0.8180(2) 0.1831(5) 0.6973(3) 0.0585(11) Uani 1 1 d . . . . .
H2 H 0.843374 0.152485 0.746492 0.070 Uiso 1 1 calc R U . . .
C26 C 0.5155(2) 0.7321(6) 0.0476(3) 0.0630(11) Uani 1 1 d . . . . .
H26 H 0.480936 0.724903 -0.007229 0.076 Uiso 1 1 calc R U . . .
C21 C 0.7440(2) 0.2602(5) 0.5527(3) 0.0585(11) Uani 1 1 d . . . . .
H21 H 0.717796 0.286461 0.502607 0.070 Uiso 1 1 calc R U . . .
C28 C 0.5164(2) 1.0881(5) 0.1511(2) 0.0496(9) Uani 1 1 d . . . . .
C25 C 0.5760(2) 0.6467(5) 0.1016(3) 0.0600(11) Uani 1 1 d . . . . .
H25 H 0.582057 0.580440 0.083402 0.072 Uiso 1 1 calc R U . . .
C29 C 0.5236(2) 1.1760(5) 0.1196(3) 0.0567(10) Uani 1 1 d . . . . .
H29 H 0.548547 1.136927 0.119710 0.068 Uiso 1 1 calc R U . . .
C27 C 0.5062(2) 0.8285(5) 0.0748(2) 0.0557(10) Uani 1 1 d . . . . .
H27 H 0.465006 0.884460 0.037889 0.067 Uiso 1 1 calc R U . . .
C1 C 0.8130(2) 0.0877(5) 0.6560(3) 0.0626(11) Uani 1 1 d . . . . .
H1 H 0.836470 -0.006747 0.679401 0.075 Uiso 1 1 calc R U . . .
C17 C 0.6752(2) 0.9924(5) 0.5968(3) 0.0547(10) Uani 1 1 d . . . . .
H17 H 0.673747 1.049691 0.569359 0.066 Uiso 1 1 calc R U . . .
C30 C 0.4932(3) 1.3230(6) 0.0878(3) 0.0673(12) Uani 1 1 d . . . . .
H30 H 0.497965 1.381240 0.066657 0.081 Uiso 1 1 calc R U . . .
C20 C 0.6793(2) 0.7549(5) 0.6403(3) 0.0578(11) Uani 1 1 d . . . . .
H20 H 0.681613 0.647052 0.641883 0.069 Uiso 1 1 calc R U . . .
C33 C 0.4777(2) 1.1470(5) 0.1494(3) 0.0579(11) Uani 1 1 d . . . . .
H33 H 0.471687 1.088048 0.169070 0.069 Uiso 1 1 calc R U . . .
C18 C 0.6740(3) 1.0666(6) 0.6365(3) 0.0648(12) Uani 1 1 d . . . . .
H18 H 0.672684 1.174419 0.636726 0.078 Uiso 1 1 calc R U . . .
C19 C 0.6748(3) 0.9789(6) 0.6757(3) 0.0698(13) Uani 1 1 d . . . . .
H19 H 0.673612 1.030629 0.701643 0.084 Uiso 1 1 calc R U . . .
C31 C 0.4562(2) 1.3832(6) 0.0872(3) 0.0685(13) Uani 1 1 d . . . . .
H31 H 0.436622 1.481746 0.066655 0.082 Uiso 1 1 calc R U . . .
C32 C 0.4487(2) 1.2928(6) 0.1183(3) 0.0687(13) Uani 1 1 d . . . . .
H32 H 0.423648 1.332180 0.117966 0.082 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
-2 0 1 0.0471
10 3 0 0.1273
-3 -1 -15 0.0871
30 -1 -17 0.0517
-30 -2 27 0.0976
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
C15 N2 C5 118.0(3) . . ?
C22 N4 C11 119.1(3) . . ?
C28 N4 C22 121.0(3) . . ?
C28 N4 C11 119.9(3) . . ?
C21 N1 C1 116.1(4) . . ?
C9 C8 C7 121.1(4) . . ?
C9 C8 C13 117.8(4) . . ?
C13 C8 C7 121.1(4) . . ?
C3 C4 C5 121.2(3) . . ?
C21 C4 C5 120.9(3) . . ?
C21 C4 C3 117.9(4) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C25 C24 C23 121.2(4) . . ?
C14 C7 C8 122.6(4) . . ?
C6 C7 C8 120.5(4) . . ?
C6 C7 C14 117.0(4) . . ?
C23 C22 N4 120.1(3) . . ?
C23 C22 C27 118.3(4) . . ?
C27 C22 N4 121.5(4) . . ?
N2 C15 C14 121.9(4) . . ?
N2 C15 C16 115.5(3) . . ?
C14 C15 C16 122.6(3) . . ?
C7 C14 C15 120.6(4) . . ?
C7 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C8 C9 H9 119.0 . . ?
C8 C9 C10 121.9(4) . . ?
C10 C9 H9 119.0 . . ?
C19 N3 C20 115.8(4) . . ?
C24 C23 C22 120.0(4) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C7 C6 H6 120.1 . . ?
C7 C6 C5 119.9(4) . . ?
C5 C6 H6 120.1 . . ?
C17 C16 C15 121.7(4) . . ?
C17 C16 C20 116.9(4) . . ?
C20 C16 C15 121.4(4) . . ?
C8 C13 H13 119.4 . . ?
C8 C13 C12 121.1(4) . . ?
C12 C13 H13 119.4 . . ?
N2 C5 C4 115.6(3) . . ?
N2 C5 C6 122.6(4) . . ?
C6 C5 C4 121.8(3) . . ?
C10 C11 N4 119.7(3) . . ?
C10 C11 C12 119.1(4) . . ?
C12 C11 N4 121.2(4) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 C4 118.8(4) . . ?
C2 C3 H3 120.6 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.9(4) . . ?
C11 C10 H10 120.1 . . ?
C13 C12 H12 119.9 . . ?
C11 C12 C13 120.2(4) . . ?
C11 C12 H12 119.9 . . ?
C3 C2 H2 120.6 . . ?
C1 C2 C3 118.7(4) . . ?
C1 C2 H2 120.6 . . ?
C25 C26 H26 119.9 . . ?
C25 C26 C27 120.2(4) . . ?
C27 C26 H26 119.9 . . ?
N1 C21 C4 124.3(4) . . ?
N1 C21 H21 117.9 . . ?
C4 C21 H21 117.9 . . ?
C29 C28 N4 121.0(4) . . ?
C29 C28 C33 119.6(4) . . ?
C33 C28 N4 119.4(4) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 C24 119.2(4) . . ?
C26 C25 H25 120.4 . . ?
C28 C29 H29 120.1 . . ?
C28 C29 C30 119.7(4) . . ?
C30 C29 H29 120.1 . . ?
C22 C27 H27 119.5 . . ?
C26 C27 C22 121.1(4) . . ?
C26 C27 H27 119.5 . . ?
N1 C1 C2 124.3(4) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 119.0(4) . . ?
C18 C17 H17 120.5 . . ?
C29 C30 H30 119.5 . . ?
C31 C30 C29 121.1(4) . . ?
C31 C30 H30 119.5 . . ?
N3 C20 C16 125.4(4) . . ?
N3 C20 H20 117.3 . . ?
C16 C20 H20 117.3 . . ?
C28 C33 H33 120.2 . . ?
C32 C33 C28 119.5(4) . . ?
C32 C33 H33 120.2 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.5(4) . . ?
C19 C18 H18 120.2 . . ?
N3 C19 C18 123.3(4) . . ?
N3 C19 H19 118.3 . . ?
C18 C19 H19 118.3 . . ?
C30 C31 H31 120.7 . . ?
C30 C31 C32 118.6(4) . . ?
C32 C31 H31 120.7 . . ?
C33 C32 C31 121.4(5) . . ?
C33 C32 H32 119.3 . . ?
C31 C32 H32 119.3 . . ?
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
N2 C15 1.347(5) . ?
N2 C5 1.356(5) . ?
N4 C22 1.429(5) . ?
N4 C11 1.437(5) . ?
N4 C28 1.416(5) . ?
N1 C21 1.343(5) . ?
N1 C1 1.344(5) . ?
C8 C7 1.487(5) . ?
C8 C9 1.389(5) . ?
C8 C13 1.389(5) . ?
C4 C5 1.482(5) . ?
C4 C3 1.397(5) . ?
C4 C21 1.386(5) . ?
C24 H24 0.9300 . ?
C24 C23 1.386(6) . ?
C24 C25 1.385(6) . ?
C7 C14 1.402(5) . ?
C7 C6 1.390(5) . ?
C22 C23 1.393(5) . ?
C22 C27 1.401(5) . ?
C15 C14 1.404(5) . ?
C15 C16 1.478(5) . ?
C14 H14 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.393(5) . ?
N3 C20 1.346(5) . ?
N3 C19 1.338(6) . ?
C23 H23 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.408(5) . ?
C16 C17 1.382(6) . ?
C16 C20 1.397(6) . ?
C13 H13 0.9300 . ?
C13 C12 1.401(5) . ?
C11 C10 1.390(5) . ?
C11 C12 1.393(5) . ?
C3 H3 0.9300 . ?
C3 C2 1.380(6) . ?
C10 H10 0.9300 . ?
C12 H12 0.9300 . ?
C2 H2 0.9300 . ?
C2 C1 1.377(6) . ?
C26 H26 0.9300 . ?
C26 C25 1.380(6) . ?
C26 C27 1.384(6) . ?
C21 H21 0.9300 . ?
C28 C29 1.392(6) . ?
C28 C33 1.399(6) . ?
C25 H25 0.9300 . ?
C29 H29 0.9300 . ?
C29 C30 1.397(6) . ?
C27 H27 0.9300 . ?
C1 H1 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.387(6) . ?
C30 H30 0.9300 . ?
C30 C31 1.374(7) . ?
C20 H20 0.9300 . ?
C33 H33 0.9300 . ?
C33 C32 1.377(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.385(7) . ?
C19 H19 0.9300 . ?
C31 H31 0.9300 . ?
C31 C32 1.400(7) . ?
C32 H32 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
N2 C15 C14 C7 -2.8(6) . . . . ?
N2 C15 C16 C17 155.5(4) . . . . ?
N2 C15 C16 C20 -25.1(5) . . . . ?
N4 C22 C23 C24 177.6(4) . . . . ?
N4 C22 C27 C26 -179.0(4) . . . . ?
N4 C11 C10 C9 176.5(4) . . . . ?
N4 C11 C12 C13 -177.8(4) . . . . ?
N4 C28 C29 C30 -178.2(4) . . . . ?
N4 C28 C33 C32 177.6(4) . . . . ?
C8 C7 C14 C15 -179.2(4) . . . . ?
C8 C7 C6 C5 -178.2(4) . . . . ?
C8 C9 C10 C11 1.4(6) . . . . ?
C8 C13 C12 C11 1.2(6) . . . . ?
C4 C3 C2 C1 0.0(6) . . . . ?
C7 C8 C9 C10 -179.8(4) . . . . ?
C7 C8 C13 C12 178.5(4) . . . . ?
C7 C6 C5 N2 -2.7(6) . . . . ?
C7 C6 C5 C4 178.6(4) . . . . ?
C22 N4 C11 C10 -41.0(5) . . . . ?
C22 N4 C11 C12 137.5(4) . . . . ?
C22 N4 C28 C29 -31.7(6) . . . . ?
C22 N4 C28 C33 149.0(4) . . . . ?
C15 N2 C5 C4 178.9(3) . . . . ?
C15 N2 C5 C6 0.1(5) . . . . ?
C15 C16 C17 C18 -179.6(4) . . . . ?
C15 C16 C20 N3 -179.3(4) . . . . ?
C14 C7 C6 C5 2.4(6) . . . . ?
C14 C15 C16 C17 -26.6(6) . . . . ?
C14 C15 C16 C20 152.9(4) . . . . ?
C9 C8 C7 C14 -139.9(4) . . . . ?
C9 C8 C7 C6 40.8(6) . . . . ?
C9 C8 C13 C12 -1.8(6) . . . . ?
C23 C24 C25 C26 -0.3(7) . . . . ?
C23 C22 C27 C26 0.8(6) . . . . ?
C6 C7 C14 C15 0.2(6) . . . . ?
C16 C15 C14 C7 179.4(4) . . . . ?
C16 C17 C18 C19 -1.2(7) . . . . ?
C13 C8 C7 C14 39.8(6) . . . . ?
C13 C8 C7 C6 -139.6(4) . . . . ?
C13 C8 C9 C10 0.5(6) . . . . ?
C5 N2 C15 C14 2.6(5) . . . . ?
C5 N2 C15 C16 -179.5(3) . . . . ?
C5 C4 C3 C2 -176.7(4) . . . . ?
C5 C4 C21 N1 176.2(4) . . . . ?
C11 N4 C22 C23 -39.3(5) . . . . ?
C11 N4 C22 C27 140.5(4) . . . . ?
C11 N4 C28 C29 147.0(4) . . . . ?
C11 N4 C28 C33 -32.2(6) . . . . ?
C3 C4 C5 N2 -12.3(5) . . . . ?
C3 C4 C5 C6 166.5(4) . . . . ?
C3 C4 C21 N1 -1.9(7) . . . . ?
C3 C2 C1 N1 -1.1(7) . . . . ?
C10 C11 C12 C13 0.8(6) . . . . ?
C12 C11 C10 C9 -2.0(6) . . . . ?
C21 N1 C1 C2 0.7(7) . . . . ?
C21 C4 C5 N2 169.7(4) . . . . ?
C21 C4 C5 C6 -11.5(6) . . . . ?
C21 C4 C3 C2 1.4(6) . . . . ?
C28 N4 C22 C23 139.4(4) . . . . ?
C28 N4 C22 C27 -40.7(6) . . . . ?
C28 N4 C11 C10 140.2(4) . . . . ?
C28 N4 C11 C12 -41.2(5) . . . . ?
C28 C29 C30 C31 0.2(7) . . . . ?
C28 C33 C32 C31 0.9(7) . . . . ?
C25 C24 C23 C22 2.0(6) . . . . ?
C25 C26 C27 C22 0.9(7) . . . . ?
C29 C28 C33 C32 -1.6(7) . . . . ?
C29 C30 C31 C32 -0.9(7) . . . . ?
C27 C22 C23 C24 -2.2(6) . . . . ?
C27 C26 C25 C24 -1.1(7) . . . . ?
C1 N1 C21 C4 0.9(7) . . . . ?
C17 C16 C20 N3 0.1(7) . . . . ?
C17 C18 C19 N3 0.5(8) . . . . ?
C30 C31 C32 C33 0.3(8) . . . . ?
C20 N3 C19 C18 0.5(8) . . . . ?
C20 C16 C17 C18 0.9(6) . . . . ?
C33 C28 C29 C30 1.1(6) . . . . ?
C19 N3 C20 C16 -0.8(7) . . . . ?
