#------------------------------------------------------------------------------
#$Date: 2020-10-06 10:33:37 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257385 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/76/1557635.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_1557635
loop_
_publ_author_name
'Odella, Emmanuel'
'Mora, S. Jimena'
'Wadsworth, Brian L.'
'Goings, Joshua J.'
'Gervaldo, Miguel A.'
'Sereno, Leonides E.'
'Groy, Thomas L.'
'Gust, Devens'
'Moore, Thomas A.'
'Moore, Gary F.'
'Hammes-Schiffer, Sharon'
'Moore, Ana L.'
_publ_section_title
;
 Proton-coupled electron transfer across benzimidazole bridges in
 bioinspired proton wires
;
_journal_issue                   15
_journal_name_full               'Chemical Science'
_journal_page_first              3820
_journal_page_last               3828
_journal_paper_doi               10.1039/C9SC06010C
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         '2(C36 H37 N5 O2), C H2 Cl2 [+ solvent]'
_chemical_formula_sum            'C73 H76 Cl2 N10 O4'
_chemical_formula_weight         1228.33
_chemical_name_common            diBIP-Imine-OMe
_chemical_name_systematic
7-(4-Methoxyphenyliminomethyl-1H-benzimidazole-2-yl)-2-(3,5-di-tert-butyl-2-hydroxyphenyl-1-yl)-1H-benzimidazole
_chemical_properties_physical    Moisture-sensitive
_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     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2019-11-26 deposited with the CCDC.	2020-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.031(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   33.136(4)
_cell_length_b                   6.8671(8)
_cell_length_c                   30.967(4)
_cell_measurement_reflns_used    3568
_cell_measurement_temperature    123.(2)
_cell_measurement_theta_max      24.9180
_cell_measurement_theta_min      2.4968
_cell_volume                     6938.8(15)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2014)'
_computing_data_collection       'Bruker Instrument Service v2015.5.1.3'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'XShell ver. 6.3.1 (Bruker AXS, 2004)'
_computing_publication_material  'Bruker APEX2 v2014.11-0 (Bruker-AXS, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL XT-2014/4'
_diffrn_ambient_temperature      123.(2)
_diffrn_detector_area_resol_mean 8.3330
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Smart APEX Diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            27063
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.98
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'sealed tube'
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'long thin plate'
_exptl_crystal_F_000             2600
_exptl_crystal_size_max          0.514
_exptl_crystal_size_mid          0.199
_exptl_crystal_size_min          0.063
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.262
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         6369
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0667
_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)+(0.0302P)²+15.7348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1470
_refine_ls_wR_factor_ref         0.1607
_reflns_number_gt                4424
_reflns_number_total             6369
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9sc06010c2.cif
_cod_data_source_block           diBIP_imine_methoxy
_cod_depositor_comments
;Adding full bibliography for 1557634--1557635.cif.

 Adding full bibliography for 1557634--1557635.cif.
;
_cod_original_cell_volume        6938.8(14)
_cod_database_code               1557635
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.59098(6) 0.3754(3) 0.25925(6) 0.0329(5) Uani d . . . 1 . .
H H1 0.5706 0.3795 0.272 0.049 Uiso calc U . R 1 . .
O O2 0.32507(6) 0.1421(3) 0.63246(7) 0.0366(5) Uani d . . . 1 . .
N N1 0.54807(7) 0.3693(3) 0.32171(7) 0.0274(5) Uani d . . . 1 . .
N N2 0.57880(7) 0.3313(3) 0.39143(7) 0.0272(5) Uani d . . . 1 . .
H H2 0.5984 0.3159 0.4143 0.033 Uiso calc U . R 1 . .
N N3 0.57878(7) 0.2759(4) 0.48095(8) 0.0387(6) Uani d . . . 1 . .
N N4 0.51987(7) 0.2484(3) 0.50630(7) 0.0284(5) Uani d . . . 1 . .
H H4 0.4934 0.2508 0.5066 0.034 Uiso calc U . R 1 . .
N N5 0.47566(7) 0.1745(3) 0.57535(8) 0.0297(6) Uani d . . . 1 . .
C C1 0.62566(8) 0.3597(4) 0.28953(9) 0.0260(6) Uani d . . . 1 . .
C C2 0.66393(8) 0.3553(4) 0.27578(9) 0.0265(6) Uani d . . . 1 . .
C C3 0.69892(8) 0.3467(4) 0.30816(9) 0.0265(6) Uani d . . . 1 . .
H H3 0.7249 0.3447 0.2992 0.032 Uiso calc U . R 1 . .
C C4 0.69780(8) 0.3408(4) 0.35318(9) 0.0276(6) Uani d . . . 1 . .
C C5 0.65966(8) 0.3393(4) 0.36546(9) 0.0269(6) Uani d . . . 1 . .
H H5 0.658 0.3325 0.3957 0.032 Uiso calc U . R 1 . .
C C6 0.62361(8) 0.3476(4) 0.33462(9) 0.0256(6) Uani d . . . 1 . .
C C7 0.66700(8) 0.3612(4) 0.22673(9) 0.0290(6) Uani d . . . 1 . .
C C8 0.64907(10) 0.5537(5) 0.20608(10) 0.0392(8) Uani d . . . 1 . .
H H8A 0.6203 0.5649 0.2096 0.059 Uiso calc U . R 1 . .
H H8B 0.6508 0.5551 0.1748 0.059 Uiso calc U . R 1 . .
H H8C 0.6647 0.6635 0.2207 0.059 Uiso calc U . R 1 . .
C C9 0.64402(10) 0.1865(4) 0.20295(10) 0.0379(8) Uani d . . . 1 . .
H H9A 0.6567 0.0652 0.2152 0.057 Uiso calc U . R 1 . .
H H9B 0.6454 0.1932 0.1716 0.057 Uiso calc U . R 1 . .
H H9C 0.6153 0.1898 0.2068 0.057 Uiso calc U . R 1 . .
C C10 0.71141(9) 0.3483(5) 0.21913(9) 0.0358(7) Uani d . . . 1 . .
H H10A 0.727 0.4594 0.2332 0.054 Uiso calc U . R 1 . .
H H10B 0.7118 0.3505 0.1876 0.054 Uiso calc U . R 1 . .
H H10C 0.7238 0.2269 0.2318 0.054 Uiso calc U . R 1 . .
C C11 0.73797(8) 0.3379(4) 0.38684(9) 0.0319(7) Uani d . . . 1 . .
C C12 0.76137(10) 0.5271(5) 0.38220(12) 0.0463(9) Uani d . . . 1 . .
H H12A 0.7868 0.5286 0.4038 0.069 Uiso calc U . R 1 . .
H H12B 0.7443 0.6387 0.3872 0.069 Uiso calc U . R 1 . .
H H12C 0.768 0.535 0.3526 0.069 Uiso calc U . R 1 . .
C C13 0.76421(9) 0.1646(5) 0.37757(11) 0.0428(8) Uani d . . . 1 . .
H H13A 0.7697 0.1739 0.3476 0.064 Uiso calc U . R 1 . .
H H13B 0.7495 0.0431 0.3809 0.064 Uiso calc U . R 1 . .
H H13C 0.7902 0.1658 0.3983 0.064 Uiso calc U . R 1 . .
C C14 0.73015(10) 0.3227(6) 0.43388(10) 0.0503(9) Uani d . . . 1 . .
H H14A 0.7564 0.3203 0.4541 0.075 Uiso calc U . R 1 . .
H H14B 0.7149 0.2028 0.4372 0.075 Uiso calc U . R 1 . .
H H14C 0.7141 0.4353 0.4405 0.075 Uiso calc U . R 1 . .
C C15 0.58376(8) 0.3480(4) 0.34865(9) 0.0264(6) Uani d . . . 1 . .
C C16 0.53760(8) 0.3430(4) 0.39212(9) 0.0275(6) Uani d . . . 1 . .
C C17 0.51612(8) 0.3305(4) 0.42727(9) 0.0277(6) Uani d . . . 1 . .
C C18 0.47379(8) 0.3500(4) 0.41629(10) 0.0303(7) Uani d . . . 1 . .
H H18 0.4577 0.3428 0.4388 0.036 Uiso calc U . R 1 . .
C C19 0.45427(9) 0.3796(4) 0.37310(10) 0.0330(7) Uani d . . . 1 . .
H H19 0.4253 0.3945 0.3671 0.04 Uiso calc U . R 1 . .
C C20 0.47596(9) 0.3880(4) 0.33876(10) 0.0328(7) Uani d . . . 1 . .
H H20 0.4623 0.4067 0.3094 0.039 Uiso calc U . R 1 . .
C C21 0.51832(8) 0.3680(4) 0.34860(9) 0.0284(6) Uani d . . . 1 . .
C C22 0.53847(9) 0.2891(4) 0.47088(9) 0.0288(6) Uani d . . . 1 . .
C C23 0.58670(9) 0.2204(5) 0.52485(10) 0.0383(8) Uani d . . . 1 . .
C C24 0.62391(10) 0.1821(7) 0.55250(11) 0.0593(11) Uani d . . . 1 . .
H H24 0.6492 0.1918 0.5422 0.071 Uiso calc U . R 1 . .
C C25 0.62262(10) 0.1299(6) 0.59524(11) 0.0559(10) Uani d . . . 1 . .
H H25 0.6476 0.1039 0.6146 0.067 Uiso calc U . R 1 . .
C C26 0.58585(9) 0.1143(5) 0.61067(10) 0.0389(8) Uani d . . . 1 . .
H H26 0.5864 0.0777 0.6403 0.047 Uiso calc U . R 1 . .
C C27 0.54848(9) 0.1504(4) 0.58421(9) 0.0298(6) Uani d . . . 1 . .
C C28 0.55011(8) 0.2034(4) 0.54088(9) 0.0286(6) Uani d . . . 1 . .
C C29 0.50985(9) 0.1348(4) 0.60002(9) 0.0310(7) Uani d . . . 1 . .
H H29 0.5099 0.094 0.6294 0.037 Uiso calc U . R 1 . .
C C30 0.43882(9) 0.1650(4) 0.59272(9) 0.0296(6) Uani d . . . 1 . .
C C31 0.43656(9) 0.1733(4) 0.63707(9) 0.0300(7) Uani d . . . 1 . .
H H31 0.4611 0.1851 0.6579 0.036 Uiso calc U . R 1 . .
C C32 0.39957(9) 0.1648(4) 0.65165(9) 0.0301(7) Uani d . . . 1 . .
H H32 0.3989 0.1701 0.6822 0.036 Uiso calc U . R 1 . .
C C33 0.36327(9) 0.1483(4) 0.62165(10) 0.0311(7) Uani d . . . 1 . .
C C34 0.36505(9) 0.1414(5) 0.57714(10) 0.0412(8) Uani d . . . 1 . .
H H34 0.3405 0.1304 0.5563 0.049 Uiso calc U . R 1 . .
C C35 0.40226(9) 0.1504(5) 0.56296(10) 0.0394(8) Uani d . . . 1 . .
H H35 0.4029 0.1465 0.5324 0.047 Uiso calc U . R 1 . .
C C36 0.32307(9) 0.1481(4) 0.67814(10) 0.0360(7) Uani d . . . 1 . .
H H36A 0.3378 0.0363 0.6929 0.054 Uiso calc U . R 1 . .
H H36B 0.2943 0.1433 0.682 0.054 Uiso calc U . R 1 . .
H H36C 0.3356 0.269 0.6909 0.054 Uiso calc U . R 1 . .
Cl Cl1A 0.53785(3) 0.86035(17) 0.23211(3) 0.0682(3) Uani d . . . 1 . .
C C1A 0.5 1.0034(7) 0.25 0.0570(14) Uani d T P S 1 . .
H H1A1 0.487 1.0882 0.2257 0.068 Uiso calc U P R 0.5 . .
H H1A2 0.513 1.0882 0.2743 0.068 Uiso calc U P R 0.5 . .
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'
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 H1 . . 109.5 ?
C33 O2 C36 . . 116.6(2) ?
C15 N1 C21 . . 105.5(2) ?
C15 N2 C16 . . 107.3(2) ?
C15 N2 H2 . . 126.3 ?
C16 N2 H2 . . 126.3 ?
C22 N3 C23 . . 105.1(2) ?
C28 N4 C22 . . 107.5(2) ?
C28 N4 H4 . . 126.3 ?
C22 N4 H4 . . 126.3 ?
C29 N5 C30 . . 119.6(2) ?
O1 C1 C2 . . 119.5(2) ?
O1 C1 C6 . . 120.5(2) ?
C2 C1 C6 . . 120.0(2) ?
C3 C2 C1 . . 117.6(2) ?
C3 C2 C7 . . 121.4(2) ?
C1 C2 C7 . . 121.1(2) ?
C2 C3 C4 . . 123.6(2) ?
C2 C3 H3 . . 118.2 ?
C4 C3 H3 . . 118.2 ?
C5 C4 C3 . . 117.3(3) ?
C5 C4 C11 . . 122.5(2) ?
C3 C4 C11 . . 120.2(2) ?
C4 C5 C6 . . 121.8(3) ?
C4 C5 H5 . . 119.1 ?
C6 C5 H5 . . 119.1 ?
C5 C6 C1 . . 119.8(2) ?
C5 C6 C15 . . 120.5(2) ?
C1 C6 C15 . . 119.7(2) ?
C10 C7 C9 . . 106.9(2) ?
C10 C7 C2 . . 112.3(2) ?
C9 C7 C2 . . 109.9(2) ?
C10 C7 C8 . . 107.2(2) ?
C9 C7 C8 . . 110.3(2) ?
C2 C7 C8 . . 110.1(2) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C7 C9 H9A . . 109.5 ?
C7 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C7 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C7 C10 H10A . . 109.5 ?
C7 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C7 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C14 C11 C13 . . 108.8(3) ?
C14 C11 C12 . . 108.7(3) ?
C13 C11 C12 . . 109.2(2) ?
C14 C11 C4 . . 112.1(2) ?
C13 C11 C4 . . 109.6(2) ?
C12 C11 C4 . . 108.5(2) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C11 C13 H13A . . 109.5 ?
C11 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C11 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C11 C14 H14A . . 109.5 ?
C11 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C11 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
N1 C15 N2 . . 111.9(2) ?
N1 C15 C6 . . 124.4(2) ?
N2 C15 C6 . . 123.7(2) ?
N2 C16 C21 . . 106.3(2) ?
N2 C16 C17 . . 130.5(3) ?
C21 C16 C17 . . 123.2(3) ?
C18 C17 C16 . . 115.5(3) ?
C18 C17 C22 . . 125.2(3) ?
C16 C17 C22 . . 119.2(2) ?
C17 C18 C19 . . 121.8(3) ?
C17 C18 H18 . . 119.1 ?
C19 C18 H18 . . 119.1 ?
C20 C19 C18 . . 121.7(3) ?
C20 C19 H19 . . 119.1 ?
C18 C19 H19 . . 119.1 ?
C19 C20 C21 . . 117.8(3) ?
C19 C20 H20 . . 121.1 ?
C21 C20 H20 . . 121.1 ?
C20 C21 N1 . . 131.2(3) ?
C20 C21 C16 . . 119.9(3) ?
N1 C21 C16 . . 108.9(2) ?
N3 C22 N4 . . 111.9(3) ?
N3 C22 C17 . . 124.4(3) ?
N4 C22 C17 . . 123.7(2) ?
N3 C23 C28 . . 110.1(3) ?
N3 C23 C24 . . 130.2(3) ?
C28 C23 C24 . . 119.7(3) ?
C25 C24 C23 . . 117.7(3) ?
C25 C24 H24 . . 121.1 ?
C23 C24 H24 . . 121.1 ?
C24 C25 C26 . . 121.8(3) ?
C24 C25 H25 . . 119.1 ?
C26 C25 H25 . . 119.1 ?
C27 C26 C25 . . 122.1(3) ?
C27 C26 H26 . . 119.0 ?
C25 C26 H26 . . 119.0 ?
C26 C27 C28 . . 115.7(3) ?
C26 C27 C29 . . 122.6(3) ?
C28 C27 C29 . . 121.7(3) ?
N4 C28 C23 . . 105.5(2) ?
N4 C28 C27 . . 131.5(3) ?
C23 C28 C27 . . 123.0(3) ?
N5 C29 C27 . . 121.6(3) ?
N5 C29 H29 . . 119.2 ?
C27 C29 H29 . . 119.2 ?
C31 C30 C35 . . 117.8(3) ?
C31 C30 N5 . . 124.8(3) ?
C35 C30 N5 . . 117.3(3) ?
C32 C31 C30 . . 121.7(3) ?
C32 C31 H31 . . 119.1 ?
C30 C31 H31 . . 119.1 ?
C31 C32 C33 . . 120.0(3) ?
C31 C32 H32 . . 120.0 ?
C33 C32 H32 . . 120.0 ?
O2 C33 C32 . . 124.7(3) ?
O2 C33 C34 . . 116.3(3) ?
C32 C33 C34 . . 118.9(3) ?
C35 C34 C33 . . 120.5(3) ?
C35 C34 H34 . . 119.7 ?
C33 C34 H34 . . 119.7 ?
C34 C35 C30 . . 121.0(3) ?
C34 C35 H35 . . 119.5 ?
C30 C35 H35 . . 119.5 ?
O2 C36 H36A . . 109.5 ?
O2 C36 H36B . . 109.5 ?
H36A C36 H36B . . 109.5 ?
O2 C36 H36C . . 109.5 ?
H36A C36 H36C . . 109.5 ?
H36B C36 H36C . . 109.5 ?
Cl1A C1A Cl1A . 2_655 112.0(3) ?
Cl1A C1A H1A1 . . 109.2 ?
Cl1A C1A H1A1 2_655 . 109.2 ?
Cl1A C1A H1A2 . . 109.2 ?
Cl1A C1A H1A2 2_655 . 109.2 ?
H1A1 C1A H1A2 . . 107.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.355(3) ?
O1 H1 . 0.84 ?
O2 C33 . 1.365(3) ?
O2 C36 . 1.428(3) ?
N1 C15 . 1.331(3) ?
N1 C21 . 1.397(3) ?
N2 C15 . 1.368(3) ?
N2 C16 . 1.371(3) ?
N2 H2 . 0.88 ?
N3 C22 . 1.321(4) ?
N3 C23 . 1.392(4) ?
N4 C28 . 1.368(3) ?
N4 C22 . 1.377(3) ?
N4 H4 . 0.88 ?
N5 C29 . 1.281(4) ?
N5 C30 . 1.419(4) ?
C1 C2 . 1.407(4) ?
C1 C6 . 1.412(4) ?
C2 C3 . 1.396(4) ?
C2 C7 . 1.540(4) ?
C3 C4 . 1.402(4) ?
C3 H3 . 0.95 ?
C4 C5 . 1.382(4) ?
C4 C11 . 1.541(4) ?
C5 C6 . 1.395(4) ?
C5 H5 . 0.95 ?
C6 C15 . 1.460(4) ?
C7 C10 . 1.533(4) ?
C7 C9 . 1.538(4) ?
C7 C8 . 1.542(4) ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
C9 H9A . 0.98 ?
C9 H9B . 0.98 ?
C9 H9C . 0.98 ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 C14 . 1.527(4) ?
C11 C13 . 1.530(4) ?
C11 C12 . 1.533(4) ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C16 C21 . 1.398(4) ?
C16 C17 . 1.403(4) ?
C17 C18 . 1.391(4) ?
C17 C22 . 1.451(4) ?
C18 C19 . 1.395(4) ?
C18 H18 . 0.95 ?
C19 C20 . 1.385(4) ?
C19 H19 . 0.95 ?
C20 C21 . 1.390(4) ?
C20 H20 . 0.95 ?
C23 C28 . 1.393(4) ?
C23 C24 . 1.398(4) ?
C24 C25 . 1.379(5) ?
C24 H24 . 0.95 ?
C25 C26 . 1.388(4) ?
C25 H25 . 0.95 ?
C26 C27 . 1.383(4) ?
C26 H26 . 0.95 ?
C27 C28 . 1.401(4) ?
C27 C29 . 1.452(4) ?
C29 H29 . 0.95 ?
C30 C31 . 1.390(4) ?
C30 C35 . 1.392(4) ?
C31 C32 . 1.379(4) ?
C31 H31 . 0.95 ?
C32 C33 . 1.390(4) ?
C32 H32 . 0.95 ?
C33 C34 . 1.391(4) ?
C34 C35 . 1.381(4) ?
C34 H34 . 0.95 ?
C35 H35 . 0.95 ?
C36 H36A . 0.98 ?
C36 H36B . 0.98 ?
C36 H36C . 0.98 ?
Cl1A C1A . 1.757(3) ?
C1A Cl1A 2_655 1.757(3) ?
C1A H1A1 . 0.99 ?
C1A H1A2 . 0.99 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N1 . 0.84 1.83 2.593(3) 151.0 ?
N2 H2 N3 . 0.88 2.29 2.798(3) 117.0 ?
N4 H4 N5 . 0.88 2.36 2.840(3) 114.3 ?
C20 H20 O1 2_655 0.95 2.53 3.434(3) 160.0 ?
C1A H1A2 N1 1_565 0.99 2.58 3.543(4) 165.5 ?
C1A H1A1 N1 2_665 0.99 2.58 3.543(4) 165.5 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . 177.5(2) ?
C6 C1 C2 C3 . . . . -2.5(4) ?
O1 C1 C2 C7 . . . . -2.1(4) ?
C6 C1 C2 C7 . . . . 177.9(2) ?
C1 C2 C3 C4 . . . . 0.5(4) ?
C7 C2 C3 C4 . . . . -179.9(2) ?
C2 C3 C4 C5 . . . . 1.4(4) ?
C2 C3 C4 C11 . . . . -178.1(2) ?
C3 C4 C5 C6 . . . . -1.4(4) ?
C11 C4 C5 C6 . . . . 178.1(3) ?
C4 C5 C6 C1 . . . . -0.6(4) ?
C4 C5 C6 C15 . . . . -179.3(3) ?
O1 C1 C6 C5 . . . . -177.4(2) ?
C2 C1 C6 C5 . . . . 2.5(4) ?
O1 C1 C6 C15 . . . . 1.3(4) ?
C2 C1 C6 C15 . . . . -178.7(2) ?
C3 C2 C7 C10 . . . . 2.2(4) ?
C1 C2 C7 C10 . . . . -178.1(3) ?
C3 C2 C7 C9 . . . . 121.0(3) ?
C1 C2 C7 C9 . . . . -59.3(3) ?
C3 C2 C7 C8 . . . . -117.2(3) ?
C1 C2 C7 C8 . . . . 62.4(3) ?
C5 C4 C11 C14 . . . . 2.9(4) ?
C3 C4 C11 C14 . . . . -177.6(3) ?
C5 C4 C11 C13 . . . . 123.9(3) ?
C3 C4 C11 C13 . . . . -56.7(3) ?
C5 C4 C11 C12 . . . . -117.0(3) ?
C3 C4 C11 C12 . . . . 62.4(3) ?
C21 N1 C15 N2 . . . . 0.6(3) ?
C21 N1 C15 C6 . . . . -177.9(3) ?
C16 N2 C15 N1 . . . . -0.2(3) ?
C16 N2 C15 C6 . . . . 178.3(3) ?
C5 C6 C15 N1 . . . . 175.1(3) ?
C1 C6 C15 N1 . . . . -3.6(4) ?
C5 C6 C15 N2 . . . . -3.2(4) ?
C1 C6 C15 N2 . . . . 178.0(2) ?
C15 N2 C16 C21 . . . . -0.3(3) ?
C15 N2 C16 C17 . . . . 178.6(3) ?
N2 C16 C17 C18 . . . . 179.6(3) ?
C21 C16 C17 C18 . . . . -1.7(4) ?
N2 C16 C17 C22 . . . . -3.5(5) ?
C21 C16 C17 C22 . . . . 175.1(3) ?
C16 C17 C18 C19 . . . . 0.1(4) ?
C22 C17 C18 C19 . . . . -176.5(3) ?
C17 C18 C19 C20 . . . . 1.1(4) ?
C18 C19 C20 C21 . . . . -0.8(4) ?
C19 C20 C21 N1 . . . . 179.8(3) ?
C19 C20 C21 C16 . . . . -0.8(4) ?
C15 N1 C21 C20 . . . . 178.8(3) ?
C15 N1 C21 C16 . . . . -0.7(3) ?
N2 C16 C21 C20 . . . . -179.0(3) ?
C17 C16 C21 C20 . . . . 2.1(4) ?
N2 C16 C21 N1 . . . . 0.6(3) ?
C17 C16 C21 N1 . . . . -178.4(2) ?
C23 N3 C22 N4 . . . . 1.1(3) ?
C23 N3 C22 C17 . . . . -175.6(3) ?
C28 N4 C22 N3 . . . . -1.0(3) ?
C28 N4 C22 C17 . . . . 175.7(3) ?
C18 C17 C22 N3 . . . . -178.2(3) ?
C16 C17 C22 N3 . . . . 5.3(4) ?
C18 C17 C22 N4 . . . . 5.4(4) ?
C16 C17 C22 N4 . . . . -171.1(3) ?
C22 N3 C23 C28 . . . . -0.8(4) ?
C22 N3 C23 C24 . . . . 179.0(4) ?
N3 C23 C24 C25 . . . . 179.7(4) ?
C28 C23 C24 C25 . . . . -0.5(6) ?
C23 C24 C25 C26 . . . . 0.3(6) ?
C24 C25 C26 C27 . . . . -0.1(6) ?
C25 C26 C27 C28 . . . . 0.1(5) ?
C25 C26 C27 C29 . . . . -179.9(3) ?
C22 N4 C28 C23 . . . . 0.5(3) ?
C22 N4 C28 C27 . . . . -179.7(3) ?
N3 C23 C28 N4 . . . . 0.2(3) ?
C24 C23 C28 N4 . . . . -179.6(3) ?
N3 C23 C28 C27 . . . . -179.7(3) ?
C24 C23 C28 C27 . . . . 0.5(5) ?
C26 C27 C28 N4 . . . . 179.8(3) ?
C29 C27 C28 N4 . . . . -0.1(5) ?
C26 C27 C28 C23 . . . . -0.3(4) ?
C29 C27 C28 C23 . . . . 179.7(3) ?
C30 N5 C29 C27 . . . . -177.4(2) ?
C26 C27 C29 N5 . . . . 177.9(3) ?
C28 C27 C29 N5 . . . . -2.2(4) ?
C29 N5 C30 C31 . . . . 20.4(4) ?
C29 N5 C30 C35 . . . . -160.9(3) ?
C35 C30 C31 C32 . . . . 0.9(4) ?
N5 C30 C31 C32 . . . . 179.5(3) ?
C30 C31 C32 C33 . . . . -0.3(4) ?
C36 O2 C33 C32 . . . . -1.7(4) ?
C36 O2 C33 C34 . . . . 179.7(3) ?
C31 C32 C33 O2 . . . . -178.8(3) ?
C31 C32 C33 C34 . . . . -0.2(4) ?
O2 C33 C34 C35 . . . . 178.8(3) ?
C32 C33 C34 C35 . . . . 0.1(5) ?
C33 C34 C35 C30 . . . . 0.5(5) ?
C31 C30 C35 C34 . . . . -1.0(5) ?
N5 C30 C35 C34 . . . . -179.7(3) ?
