#------------------------------------------------------------------------------
#$Date: 2024-09-06 02:13:37 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294424 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/33/7133339.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_7133339
loop_
_publ_author_name
'Balasubramani, Alagesan'
'Sudarshana, K. A.'
'Kushwaha, Roli'
'Chakravarty, Sumana'
'Pabbaraja, Srihari'
'Mehta, Goverdhan'
_publ_section_title
;
 One flask cascade approach to a complex
 pyrano[2,3-c]pyrazole-pyrazolone hybrid heterocyclic system and
 its initiatory neurobiological profiling.
;
_journal_issue                   64
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8443
_journal_page_last               8446
_journal_paper_doi               10.1039/d4cc02813a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C37 H26 Cl2 N4 O2'
_chemical_formula_sum            'C37 H26 Cl2 N4 O2'
_chemical_formula_weight         629.52
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-07-06
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-01-10 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                103.225(15)
_cell_angle_beta                 106.099(14)
_cell_angle_gamma                98.327(16)
_cell_formula_units_Z            2
_cell_length_a                   9.724(7)
_cell_length_b                   12.297(9)
_cell_length_c                   13.872(10)
_cell_measurement_reflns_used    8770
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      28.184
_cell_measurement_theta_min      2.223
_cell_volume                     1512.5(19)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27040
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.402
_diffrn_reflns_theta_min         2.236
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            'metallic brownish brown'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       needle
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.115
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         7527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0476
_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)+(0.0477P)²+0.4117P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1355
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4613
_reflns_number_total             7527
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc02813a3.cif
_cod_data_source_block           kb1059_0m
_cod_depositor_comments
'Adding full bibliography for 7133337--7133339.cif.'
_cod_original_cell_volume        1512.5(18)
_cod_database_code               7133339
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C8(H8), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18),
 C19(H19), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C31(H31),
  C32(H32), C33(H33), C34(H34), C35(H35)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C37(H37A,H37B,H37C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
Cl1 Cl 1.48167(9) 0.29615(6) 1.00799(5) 0.1067(3) Uani 1 1 d . . . . .
Cl2 Cl -0.20048(7) 0.10868(7) -0.05292(6) 0.1099(3) Uani 1 1 d . . . . .
O1 O 0.46551(14) 0.39122(11) 0.30947(11) 0.0609(4) Uani 1 1 d . . . . .
O2 O 1.10341(12) 0.60251(10) 0.71890(9) 0.0485(3) Uani 1 1 d . . . . .
N1 N 1.03056(15) 0.40446(13) 0.68790(11) 0.0464(4) Uani 1 1 d . . . . .
N2 N 0.29907(15) 0.48279(13) 0.22564(11) 0.0477(4) Uani 1 1 d . . . . .
N3 N 0.28721(16) 0.59450(14) 0.22669(12) 0.0519(4) Uani 1 1 d . . . . .
N4 N 0.91791(15) 0.31464(13) 0.62017(12) 0.0483(4) Uani 1 1 d . . . . .
C1 C 1.3486(3) 0.33267(19) 0.91712(15) 0.0641(6) Uani 1 1 d . . . . .
C2 C 1.3890(2) 0.41329(18) 0.87091(15) 0.0600(5) Uani 1 1 d . . . . .
H2 H 1.487067 0.450176 0.889869 0.072 Uiso 1 1 calc R U . . .
C3 C 1.2830(2) 0.43948(17) 0.79578(14) 0.0514(5) Uani 1 1 d . . . . .
H3 H 1.308812 0.494461 0.763890 0.062 Uiso 1 1 calc R U . . .
C4 C 1.13976(19) 0.38367(16) 0.76883(13) 0.0456(4) Uani 1 1 d . . . . .
C5 C 1.00984(17) 0.50190(15) 0.66565(13) 0.0417(4) Uani 1 1 d . . . . .
C6 C 0.88277(17) 0.48127(15) 0.58412(13) 0.0412(4) Uani 1 1 d . . . . .
C7 C 0.83637(17) 0.57563(15) 0.55018(13) 0.0413(4) Uani 1 1 d . . . . .
C8 C 0.70285(18) 0.55904(16) 0.47388(13) 0.0460(4) Uani 1 1 d . . . . .
H8 H 0.652300 0.482949 0.444237 0.055 Uiso 1 1 calc R U . . .
C9 C 0.63039(18) 0.63844(15) 0.43343(13) 0.0428(4) Uani 1 1 d . . . . .
C10 C 0.49995(18) 0.60015(15) 0.35048(13) 0.0432(4) Uani 1 1 d . . . . .
C11 C 0.42747(18) 0.47952(16) 0.29797(13) 0.0442(4) Uani 1 1 d . . . . .
C12 C 0.18097(18) 0.39188(17) 0.15980(13) 0.0476(4) Uani 1 1 d . . . . .
C13 C 0.0579(2) 0.41679(19) 0.09812(15) 0.0577(5) Uani 1 1 d . . . . .
H13 H 0.054423 0.492505 0.100476 0.069 Uiso 1 1 calc R U . . .
C14 C -0.0594(2) 0.3295(2) 0.03325(17) 0.0691(6) Uani 1 1 d . . . . .
H14 H -0.142023 0.346159 -0.008383 0.083 Uiso 1 1 calc R U . . .
C15 C -0.0541(2) 0.2186(2) 0.03026(17) 0.0668(6) Uani 1 1 d . . . . .
C16 C 1.2048(3) 0.2789(2) 0.89238(16) 0.0691(6) Uani 1 1 d . . . . .
H16 H 1.179075 0.225662 0.925980 0.083 Uiso 1 1 calc R U . . .
C17 C 1.0987(2) 0.30425(18) 0.81727(15) 0.0589(5) Uani 1 1 d . . . . .
H17 H 1.000519 0.268285 0.799413 0.071 Uiso 1 1 calc R U . . .
C18 C 0.0658(2) 0.1930(2) 0.09185(17) 0.0687(6) Uani 1 1 d . . . . .
H18 H 0.067480 0.117204 0.090102 0.082 Uiso 1 1 calc R U . . .
C19 C 0.1841(2) 0.27937(18) 0.15648(15) 0.0598(5) Uani 1 1 d . . . . .
H19 H 0.266137 0.261841 0.197886 0.072 Uiso 1 1 calc R U . . .
C20 C 0.40299(19) 0.66261(16) 0.29832(14) 0.0471(4) Uani 1 1 d . . . . .
C21 C 0.4155(2) 0.78766(18) 0.31279(18) 0.0672(6) Uani 1 1 d . . . . .
H21A H 0.493157 0.817085 0.289120 0.101 Uiso 1 1 calc R U . . .
H21B H 0.436830 0.825989 0.385536 0.101 Uiso 1 1 calc R U . . .
H21C H 0.324607 0.800646 0.273049 0.101 Uiso 1 1 calc R U . . .
C22 C 0.68964(18) 0.76387(15) 0.48153(14) 0.0447(4) Uani 1 1 d . . . . .
C23 C 0.67827(19) 0.81519(17) 0.57785(15) 0.0527(5) Uani 1 1 d . . . . .
H23 H 0.634463 0.771065 0.612102 0.063 Uiso 1 1 calc R U . . .
C24 C 0.7314(2) 0.93126(19) 0.62331(18) 0.0683(6) Uani 1 1 d . . . . .
H24 H 0.722685 0.965144 0.687874 0.082 Uiso 1 1 calc R U . . .
C25 C 0.7970(2) 0.9971(2) 0.5742(2) 0.0751(7) Uani 1 1 d . . . . .
H25 H 0.831747 1.075575 0.604767 0.090 Uiso 1 1 calc R U . . .
C26 C 0.8114(2) 0.9466(2) 0.4796(2) 0.0734(6) Uani 1 1 d . . . . .
H26 H 0.857506 0.990858 0.446559 0.088 Uiso 1 1 calc R U . . .
C27 C 0.7578(2) 0.83072(18) 0.43328(17) 0.0597(5) Uani 1 1 d . . . . .
H27 H 0.767542 0.797252 0.368968 0.072 Uiso 1 1 calc R U . . .
C28 C 0.94323(18) 0.68156(15) 0.60428(13) 0.0451(4) Uani 1 1 d . . . . .
H28 H 0.926028 0.746108 0.582882 0.054 Uiso 1 1 calc R U . . .
C29 C 1.06595(18) 0.69377(15) 0.68343(13) 0.0438(4) Uani 1 1 d . . . . .
C30 C 1.17786(19) 0.79923(16) 0.74021(13) 0.0476(4) Uani 1 1 d . . . . .
C31 C 1.1470(2) 0.90445(19) 0.73716(19) 0.0724(6) Uani 1 1 d . . . . .
H31 H 1.052185 0.909027 0.702691 0.087 Uiso 1 1 calc R U . . .
C32 C 1.2553(3) 1.0025(2) 0.7846(2) 0.0903(8) Uani 1 1 d . . . . .
H32 H 1.233755 1.072991 0.780695 0.108 Uiso 1 1 calc R U . . .
C33 C 1.3942(3) 0.9977(2) 0.8376(2) 0.0875(8) Uani 1 1 d . . . . .
H33 H 1.467051 1.064536 0.869968 0.105 Uiso 1 1 calc R U . . .
C34 C 1.4255(2) 0.8950(2) 0.84258(19) 0.0811(7) Uani 1 1 d . . . . .
H34 H 1.519910 0.891681 0.879162 0.097 Uiso 1 1 calc R U . . .
C35 C 1.3189(2) 0.79566(19) 0.79413(16) 0.0632(6) Uani 1 1 d . . . . .
H35 H 1.342022 0.725574 0.797693 0.076 Uiso 1 1 calc R U . . .
C36 C 0.83092(18) 0.36098(15) 0.55862(13) 0.0437(4) Uani 1 1 d . . . . .
C37 C 0.6984(2) 0.28512(17) 0.47473(15) 0.0555(5) Uani 1 1 d . . . . .
H37A H 0.701052 0.206512 0.470756 0.083 Uiso 1 1 calc R U . . .
H37B H 0.696662 0.298636 0.408974 0.083 Uiso 1 1 calc R U . . .
H37C H 0.611968 0.301207 0.490274 0.083 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 0.0033 0.0016 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O2 C29 114.29(13) . . ?
N4 N1 C4 119.43(15) . . ?
C5 N1 N4 109.74(14) . . ?
C5 N1 C4 130.74(15) . . ?
N3 N2 C12 118.68(14) . . ?
C11 N2 N3 112.06(14) . . ?
C11 N2 C12 129.11(16) . . ?
C20 N3 N2 107.31(14) . . ?
C36 N4 N1 105.37(15) . . ?
C2 C1 Cl1 119.51(18) . . ?
C2 C1 C16 121.54(18) . . ?
C16 C1 Cl1 118.94(18) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.4(2) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.22(19) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 N1 120.15(16) . . ?
C3 C4 C17 121.29(17) . . ?
C17 C4 N1 118.54(17) . . ?
O2 C5 C6 127.64(16) . . ?
N1 C5 O2 122.35(15) . . ?
N1 C5 C6 110.01(15) . . ?
C5 C6 C7 119.19(16) . . ?
C5 C6 C36 102.87(15) . . ?
C36 C6 C7 137.92(15) . . ?
C6 C7 C28 111.94(15) . . ?
C8 C7 C6 120.63(16) . . ?
C8 C7 C28 127.43(17) . . ?
C7 C8 H8 114.6 . . ?
C7 C8 C9 130.73(17) . . ?
C9 C8 H8 114.6 . . ?
C8 C9 C22 120.61(15) . . ?
C10 C9 C8 120.19(17) . . ?
C10 C9 C22 119.16(15) . . ?
C9 C10 C11 124.81(15) . . ?
C9 C10 C20 130.90(17) . . ?
C20 C10 C11 104.25(15) . . ?
O1 C11 N2 124.40(16) . . ?
O1 C11 C10 131.12(16) . . ?
N2 C11 C10 104.47(15) . . ?
C13 C12 N2 118.84(18) . . ?
C19 C12 N2 121.72(16) . . ?
C19 C12 C13 119.43(17) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 Cl2 119.81(17) . . ?
C14 C15 C18 120.7(2) . . ?
C18 C15 Cl2 119.5(2) . . ?
C1 C16 H16 120.3 . . ?
C1 C16 C17 119.3(2) . . ?
C17 C16 H16 120.3 . . ?
C4 C17 H17 120.4 . . ?
C16 C17 C4 119.2(2) . . ?
C16 C17 H17 120.4 . . ?
C15 C18 H18 120.0 . . ?
C15 C18 C19 120.1(2) . . ?
C19 C18 H18 120.0 . . ?
C12 C19 H19 120.0 . . ?
C18 C19 C12 119.94(19) . . ?
C18 C19 H19 120.0 . . ?
N3 C20 C10 111.88(17) . . ?
N3 C20 C21 116.97(16) . . ?
C10 C20 C21 131.15(16) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C9 119.47(16) . . ?
C27 C22 C9 121.79(18) . . ?
C27 C22 C23 118.73(18) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.4(2) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.5(2) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 H25 120.2 . . ?
C24 C25 C26 119.6(2) . . ?
C26 C25 H25 120.2 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.3(2) . . ?
C27 C26 H26 119.8 . . ?
C22 C27 H27 119.7 . . ?
C26 C27 C22 120.5(2) . . ?
C26 C27 H27 119.7 . . ?
C7 C28 H28 117.7 . . ?
C29 C28 C7 124.57(17) . . ?
C29 C28 H28 117.7 . . ?
O2 C29 C30 111.36(15) . . ?
C28 C29 O2 122.10(16) . . ?
C28 C29 C30 126.51(17) . . ?
C31 C30 C29 120.74(17) . . ?
C31 C30 C35 118.33(18) . . ?
C35 C30 C29 120.86(18) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 C30 120.4(2) . . ?
C32 C31 H31 119.8 . . ?
C31 C32 H32 119.7 . . ?
C33 C32 C31 120.6(2) . . ?
C33 C32 H32 119.7 . . ?
C32 C33 H33 120.2 . . ?
C34 C33 C32 119.6(2) . . ?
C34 C33 H33 120.2 . . ?
C33 C34 H34 119.7 . . ?
C33 C34 C35 120.6(2) . . ?
C35 C34 H34 119.7 . . ?
C30 C35 H35 119.8 . . ?
C34 C35 C30 120.4(2) . . ?
C34 C35 H35 119.8 . . ?
N4 C36 C6 111.99(15) . . ?
N4 C36 C37 118.59(17) . . ?
C6 C36 C37 129.42(16) . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 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
Cl1 C1 1.729(2) . ?
Cl2 C15 1.733(2) . ?
O1 C11 1.226(2) . ?
O2 C5 1.337(2) . ?
O2 C29 1.380(2) . ?
N1 N4 1.381(2) . ?
N1 C4 1.415(2) . ?
N1 C5 1.333(2) . ?
N2 N3 1.392(2) . ?
N2 C11 1.380(2) . ?
N2 C12 1.408(2) . ?
N3 C20 1.297(2) . ?
N4 C36 1.316(2) . ?
C1 C2 1.366(3) . ?
C1 C16 1.368(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.367(3) . ?
C4 C17 1.379(3) . ?
C5 C6 1.369(2) . ?
C6 C7 1.434(2) . ?
C6 C36 1.419(3) . ?
C7 C8 1.382(2) . ?
C7 C28 1.438(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.413(2) . ?
C9 C10 1.387(2) . ?
C9 C22 1.488(3) . ?
C10 C11 1.465(3) . ?
C10 C20 1.445(2) . ?
C12 C13 1.384(3) . ?
C12 C19 1.379(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.363(3) . ?
C15 C18 1.366(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.376(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.376(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.487(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.383(3) . ?
C22 C27 1.379(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.377(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.367(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.371(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.377(3) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C28 C29 1.341(2) . ?
C29 C30 1.461(3) . ?
C30 C31 1.377(3) . ?
C30 C35 1.381(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.371(3) . ?
C32 H32 0.9300 . ?
C32 C33 1.365(4) . ?
C33 H33 0.9300 . ?
C33 C34 1.353(4) . ?
C34 H34 0.9300 . ?
C34 C35 1.375(3) . ?
C35 H35 0.9300 . ?
C36 C37 1.486(2) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
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
Cl1 C1 C2 C3 177.82(15) . . . . ?
Cl1 C1 C16 C17 -177.57(17) . . . . ?
Cl2 C15 C18 C19 178.52(18) . . . . ?
O2 C5 C6 C7 -2.0(3) . . . . ?
O2 C5 C6 C36 179.47(17) . . . . ?
O2 C29 C30 C31 -163.17(18) . . . . ?
O2 C29 C30 C35 19.9(3) . . . . ?
N1 N4 C36 C6 -0.3(2) . . . . ?
N1 N4 C36 C37 179.09(15) . . . . ?
N1 C4 C17 C16 176.70(18) . . . . ?
N1 C5 C6 C7 177.47(15) . . . . ?
N1 C5 C6 C36 -1.02(19) . . . . ?
N2 N3 C20 C10 -0.3(2) . . . . ?
N2 N3 C20 C21 179.17(17) . . . . ?
N2 C12 C13 C14 -179.79(18) . . . . ?
N2 C12 C19 C18 179.33(19) . . . . ?
N3 N2 C11 O1 -177.34(17) . . . . ?
N3 N2 C11 C10 1.56(19) . . . . ?
N3 N2 C12 C13 0.4(3) . . . . ?
N3 N2 C12 C19 -178.65(17) . . . . ?
N4 N1 C4 C3 141.95(18) . . . . ?
N4 N1 C4 C17 -36.4(2) . . . . ?
N4 N1 C5 O2 -179.56(15) . . . . ?
N4 N1 C5 C6 0.9(2) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C1 C16 C17 C4 -0.2(3) . . . . ?
C2 C1 C16 C17 1.7(4) . . . . ?
C2 C3 C4 N1 -176.42(17) . . . . ?
C2 C3 C4 C17 1.9(3) . . . . ?
C3 C4 C17 C16 -1.6(3) . . . . ?
C4 N1 N4 C36 176.52(15) . . . . ?
C4 N1 C5 O2 4.0(3) . . . . ?
C4 N1 C5 C6 -175.50(17) . . . . ?
C5 O2 C29 C28 2.0(2) . . . . ?
C5 O2 C29 C30 -176.03(14) . . . . ?
C5 N1 N4 C36 -0.35(19) . . . . ?
C5 N1 C4 C3 -41.9(3) . . . . ?
C5 N1 C4 C17 139.7(2) . . . . ?
C5 C6 C7 C8 -174.72(16) . . . . ?
C5 C6 C7 C28 5.3(2) . . . . ?
C5 C6 C36 N4 0.8(2) . . . . ?
C5 C6 C36 C37 -178.50(18) . . . . ?
C6 C7 C8 C9 175.22(18) . . . . ?
C6 C7 C28 C29 -5.5(3) . . . . ?
C7 C6 C36 N4 -177.2(2) . . . . ?
C7 C6 C36 C37 3.5(4) . . . . ?
C7 C8 C9 C10 175.28(18) . . . . ?
C7 C8 C9 C22 -7.0(3) . . . . ?
C7 C28 C29 O2 1.9(3) . . . . ?
C7 C28 C29 C30 179.60(17) . . . . ?
C8 C7 C28 C29 174.58(18) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C8 C9 C10 C20 177.29(18) . . . . ?
C8 C9 C22 C23 -72.6(2) . . . . ?
C8 C9 C22 C27 106.6(2) . . . . ?
C9 C10 C11 O1 -4.6(3) . . . . ?
C9 C10 C11 N2 176.64(16) . . . . ?
C9 C10 C20 N3 -176.87(18) . . . . ?
C9 C10 C20 C21 3.7(3) . . . . ?
C9 C22 C23 C24 -179.53(17) . . . . ?
C9 C22 C27 C26 179.92(18) . . . . ?
C10 C9 C22 C23 105.2(2) . . . . ?
C10 C9 C22 C27 -75.7(2) . . . . ?
C11 N2 N3 C20 -0.8(2) . . . . ?
C11 N2 C12 C13 175.53(18) . . . . ?
C11 N2 C12 C19 -3.5(3) . . . . ?
C11 C10 C20 N3 1.2(2) . . . . ?
C11 C10 C20 C21 -178.2(2) . . . . ?
C12 N2 N3 C20 175.10(16) . . . . ?
C12 N2 C11 O1 7.3(3) . . . . ?
C12 N2 C11 C10 -173.83(16) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C12 C19 C18 0.3(3) . . . . ?
C13 C14 C15 Cl2 -178.95(17) . . . . ?
C13 C14 C15 C18 0.7(4) . . . . ?
C14 C15 C18 C19 -1.2(4) . . . . ?
C15 C18 C19 C12 0.6(3) . . . . ?
C16 C1 C2 C3 -1.4(3) . . . . ?
C19 C12 C13 C14 -0.7(3) . . . . ?
C20 C10 C11 O1 177.2(2) . . . . ?
C20 C10 C11 N2 -1.62(18) . . . . ?
C22 C9 C10 C11 -178.22(16) . . . . ?
C22 C9 C10 C20 -0.4(3) . . . . ?
C22 C23 C24 C25 -0.5(3) . . . . ?
C23 C22 C27 C26 -0.9(3) . . . . ?
C23 C24 C25 C26 -0.8(3) . . . . ?
C24 C25 C26 C27 1.2(3) . . . . ?
C25 C26 C27 C22 -0.3(3) . . . . ?
C27 C22 C23 C24 1.3(3) . . . . ?
C28 C7 C8 C9 -4.8(3) . . . . ?
C28 C29 C30 C31 18.9(3) . . . . ?
C28 C29 C30 C35 -158.0(2) . . . . ?
C29 O2 C5 N1 178.64(16) . . . . ?
C29 O2 C5 C6 -1.9(3) . . . . ?
C29 C30 C31 C32 -175.5(2) . . . . ?
C29 C30 C35 C34 176.5(2) . . . . ?
C30 C31 C32 C33 -1.5(4) . . . . ?
C31 C30 C35 C34 -0.5(3) . . . . ?
C31 C32 C33 C34 0.4(5) . . . . ?
C32 C33 C34 C35 0.6(4) . . . . ?
C33 C34 C35 C30 -0.5(4) . . . . ?
C35 C30 C31 C32 1.5(4) . . . . ?
C36 C6 C7 C8 3.1(3) . . . . ?
C36 C6 C7 C28 -176.9(2) . . . . ?
