#------------------------------------------------------------------------------
#$Date: 2022-04-07 03:34:54 +0300 (Thu, 07 Apr 2022) $
#$Revision: 274412 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/86/7158626.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_7158626
loop_
_publ_author_name
'Mandal, Rahul Dev'
'Saha, Moumita'
'Das, Asish R.'
_publ_section_title
;
 Accessing oxy-functionalized N-heterocycles through rose bengal and TBHP
 integrated photoredox C(sp³)-O cross-coupling.
;
_journal_issue                   14
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2939
_journal_page_last               2963
_journal_paper_doi               10.1039/d2ob00381c
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C36 H22 Cl2 N4 O5'
_chemical_formula_sum            'C36 H22 Cl2 N4 O5'
_chemical_formula_weight         661.47
_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_method           SHELXL-2016/6
_audit_update_record
;
2021-08-18 deposited with the CCDC.	2022-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                92.200(7)
_cell_angle_beta                 101.408(7)
_cell_angle_gamma                92.387(7)
_cell_formula_units_Z            2
_cell_length_a                   8.346(4)
_cell_length_b                   12.269(6)
_cell_length_c                   14.899(7)
_cell_measurement_reflns_used    5760
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.72
_cell_volume                     1492.5(12)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30198
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.396
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.4562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       square
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.48
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         5261
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0431
_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)+(0.1000P)²+0.9785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1600
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4292
_reflns_number_total             5261
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00381c2.cif
_cod_data_source_block           ARDRDMCL_0m
_cod_original_cell_volume        1492.5(13)
_cod_database_code               7158626
_shelx_shelxl_version_number     2016/6
_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.
;
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 0.97854(9) 0.16981(5) 1.01851(5) 0.0565(2) Uani 1 1 d . . . . .
Cl2 Cl 0.85583(11) 0.47734(6) 0.77385(5) 0.0604(3) Uani 1 1 d . . . . .
O1 O 0.50403(19) 0.72200(12) 0.83423(11) 0.0359(4) Uani 1 1 d . . . . .
O2 O 0.46958(19) 0.53757(12) 0.80069(10) 0.0343(4) Uani 1 1 d . . . . .
O3 O 0.6896(3) 0.66392(15) 0.98597(13) 0.0554(5) Uani 1 1 d . . . . .
O4 O 0.2216(3) 0.48210(18) 0.44017(14) 0.0737(7) Uani 1 1 d . . . . .
O5 O 0.8464(2) 1.08982(14) 0.79322(13) 0.0497(5) Uani 1 1 d . . . . .
N1 N 0.7938(2) 0.90591(14) 0.76713(14) 0.0341(4) Uani 1 1 d . . . . .
N2 N 0.7114(2) 0.81007(14) 0.78282(14) 0.0346(4) Uani 1 1 d . . . . .
N3 N 0.4401(2) 0.59589(15) 0.65505(13) 0.0345(4) Uani 1 1 d . . . . .
N4 N 0.3744(2) 0.58322(16) 0.56229(13) 0.0363(4) Uani 1 1 d . . . . .
C1 C 1.1816(4) 0.8470(3) 0.6318(3) 0.0722(10) Uani 1 1 d . . . . .
H1 H 1.268548 0.834097 0.602828 0.087 Uiso 1 1 calc R U . . .
C2 C 1.1083(4) 0.9448(3) 0.6244(3) 0.0762(11) Uani 1 1 d . . . . .
H3 H 1.145108 0.997905 0.589277 0.091 Uiso 1 1 calc R U . . .
C3 C 0.9802(4) 0.9664(2) 0.6681(2) 0.0609(8) Uani 1 1 d . . . . .
H4 H 0.930437 1.032873 0.661847 0.073 Uiso 1 1 calc R U . . .
C4 C 0.9273(3) 0.8874(2) 0.72129(17) 0.0382(5) Uani 1 1 d . . . . .
C5 C 0.5854(3) 0.81651(17) 0.81826(15) 0.0299(5) Uani 1 1 d . . . . .
C6 C 0.5873(3) 0.62465(16) 0.82696(16) 0.0324(5) Uani 1 1 d . . . . .
H12 H 0.660306 0.630925 0.783162 0.039 Uiso 1 1 calc R U . . .
C7 C 0.4045(3) 0.52326(17) 0.70832(15) 0.0307(5) Uani 1 1 d . . . . .
C8 C 0.4220(3) 0.6728(2) 0.51166(17) 0.0399(5) Uani 1 1 d . . . . .
C9 C 0.3329(4) 0.6950(3) 0.4265(2) 0.0594(8) Uani 1 1 d . . . . .
H14 H 0.243176 0.649561 0.399072 0.071 Uiso 1 1 calc R U . . .
C10 C 0.3774(5) 0.7850(3) 0.3821(2) 0.0779(10) Uani 1 1 d . . . . .
H15 H 0.317829 0.798678 0.324283 0.094 Uiso 1 1 calc R U . . .
C11 C 0.5064(5) 0.8538(3) 0.4210(3) 0.0743(10) Uani 1 1 d . . . . .
H2 H 0.534371 0.914524 0.390800 0.089 Uiso 1 1 calc R U . . .
C12 C 0.7576(3) 1.00828(18) 0.79789(16) 0.0344(5) Uani 1 1 d . . . . .
C13 C 0.6075(3) 1.01201(17) 0.83439(15) 0.0332(5) Uani 1 1 d . . . . .
C14 C 0.5525(3) 1.11262(19) 0.85949(18) 0.0432(6) Uani 1 1 d . . . . .
H5 H 0.611597 1.176929 0.853389 0.052 Uiso 1 1 calc R U . . .
C15 C 0.4112(4) 1.1163(2) 0.8931(2) 0.0506(7) Uani 1 1 d . . . . .
H6 H 0.375634 1.183369 0.910241 0.061 Uiso 1 1 calc R U . . .
C16 C 0.3208(3) 1.0214(2) 0.9019(2) 0.0516(7) Uani 1 1 d . . . . .
H7 H 0.223920 1.025306 0.923555 0.062 Uiso 1 1 calc R U . . .
C17 C 0.3739(3) 0.9214(2) 0.87868(18) 0.0419(6) Uani 1 1 d . . . . .
H8 H 0.314266 0.857608 0.885558 0.050 Uiso 1 1 calc R U . . .
C18 C 0.5178(3) 0.91633(17) 0.84478(15) 0.0318(5) Uani 1 1 d . . . . .
C19 C 0.6823(3) 0.59882(18) 0.92255(16) 0.0342(5) Uani 1 1 d . . . . .
C20 C 0.7582(3) 0.49051(18) 0.93902(15) 0.0321(5) Uani 1 1 d . . . . .
C21 C 0.8346(3) 0.43072(19) 0.87961(15) 0.0352(5) Uani 1 1 d . . . . .
C22 C 0.9033(3) 0.33244(19) 0.90368(16) 0.0385(5) Uani 1 1 d . . . . .
H9 H 0.954443 0.293508 0.863524 0.046 Uiso 1 1 calc R U . . .
C23 C 0.8943(3) 0.29319(19) 0.98855(17) 0.0383(5) Uani 1 1 d . . . . .
C24 C 0.8201(3) 0.3497(2) 1.04931(17) 0.0443(6) Uani 1 1 d . . . . .
H10 H 0.814538 0.322427 1.106075 0.053 Uiso 1 1 calc R U . . .
C25 C 0.7538(3) 0.4480(2) 1.02384(16) 0.0414(6) Uani 1 1 d . . . . .
H11 H 0.704601 0.487115 1.064828 0.050 Uiso 1 1 calc R U . . .
C26 C 0.5541(4) 0.7417(2) 0.5513(2) 0.0551(7) Uani 1 1 d . . . . .
H13 H 0.616002 0.727544 0.608370 0.066 Uiso 1 1 calc R U . . .
C27 C 0.5941(4) 0.8322(3) 0.5056(2) 0.0696(9) Uani 1 1 d . . . . .
H16 H 0.682202 0.878992 0.532927 0.084 Uiso 1 1 calc R U . . .
C28 C 0.2710(3) 0.4946(2) 0.52287(18) 0.0448(6) Uani 1 1 d . . . . .
C29 C 0.2289(3) 0.41635(19) 0.58809(17) 0.0402(5) Uani 1 1 d . . . . .
C30 C 0.1196(4) 0.3277(2) 0.5552(2) 0.0568(7) Uani 1 1 d . . . . .
H17 H 0.072734 0.319606 0.493121 0.068 Uiso 1 1 calc R U . . .
C31 C 0.0818(4) 0.2531(2) 0.6145(2) 0.0595(8) Uani 1 1 d . . . . .
H18 H 0.008496 0.194476 0.592478 0.071 Uiso 1 1 calc R U . . .
C32 C 0.1516(4) 0.2636(2) 0.7073(2) 0.0520(7) Uani 1 1 d . . . . .
H19 H 0.125585 0.211633 0.746597 0.062 Uiso 1 1 calc R U . . .
C33 C 0.2592(3) 0.35068(19) 0.74165(18) 0.0425(6) Uani 1 1 d . . . . .
H20 H 0.305939 0.357712 0.803782 0.051 Uiso 1 1 calc R U . . .
C34 C 0.2968(3) 0.42842(18) 0.68125(16) 0.0343(5) Uani 1 1 d . . . . .
C35 C 0.9978(3) 0.7875(2) 0.72670(19) 0.0474(6) Uani 1 1 d . . . . .
H21 H 0.959761 0.733082 0.760087 0.057 Uiso 1 1 calc R U . . .
C36 C 1.1257(4) 0.7688(3) 0.6820(2) 0.0642(8) Uani 1 1 d . . . . .
H22 H 1.174122 0.701789 0.686521 0.077 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C6 115.78(16) . . ?
C7 O2 C6 116.29(16) . . ?
C12 N1 N2 123.22(19) . . ?
C12 N1 C4 123.54(19) . . ?
N2 N1 C4 113.12(17) . . ?
C5 N2 N1 118.75(18) . . ?
C7 N3 N4 118.89(19) . . ?
N3 N4 C28 123.47(19) . . ?
N3 N4 C8 112.46(19) . . ?
C28 N4 C8 124.1(2) . . ?
C36 C1 C2 119.1(3) . . ?
C36 C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
C1 C2 C3 121.4(3) . . ?
C1 C2 H3 119.3 . . ?
C3 C2 H3 119.3 . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H4 120.5 . . ?
C2 C3 H4 120.5 . . ?
C35 C4 C3 119.7(2) . . ?
C35 C4 N1 119.3(2) . . ?
C3 C4 N1 120.9(2) . . ?
N2 C5 O1 118.92(19) . . ?
N2 C5 C18 125.7(2) . . ?
O1 C5 C18 115.40(19) . . ?
O2 C6 O1 108.32(18) . . ?
O2 C6 C19 105.62(17) . . ?
O1 C6 C19 108.97(18) . . ?
O2 C6 H12 111.2 . . ?
O1 C6 H12 111.2 . . ?
C19 C6 H12 111.2 . . ?
N3 C7 O2 118.22(19) . . ?
N3 C7 C34 125.9(2) . . ?
O2 C7 C34 115.88(19) . . ?
C26 C8 C9 119.1(2) . . ?
C26 C8 N4 119.3(2) . . ?
C9 C8 N4 121.5(2) . . ?
C8 C9 C10 119.8(3) . . ?
C8 C9 H14 120.1 . . ?
C10 C9 H14 120.1 . . ?
C11 C10 C9 121.4(3) . . ?
C11 C10 H15 119.3 . . ?
C9 C10 H15 119.3 . . ?
C10 C11 C27 118.8(3) . . ?
C10 C11 H2 120.6 . . ?
C27 C11 H2 120.6 . . ?
O5 C12 N1 121.3(2) . . ?
O5 C12 C13 123.2(2) . . ?
N1 C12 C13 115.44(19) . . ?
C18 C13 C14 119.2(2) . . ?
C18 C13 C12 121.0(2) . . ?
C14 C13 C12 119.8(2) . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H5 120.1 . . ?
C13 C14 H5 120.1 . . ?
C14 C15 C16 120.9(2) . . ?
C14 C15 H6 119.6 . . ?
C16 C15 H6 119.6 . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H7 119.9 . . ?
C15 C16 H7 119.9 . . ?
C16 C17 C18 119.6(2) . . ?
C16 C17 H8 120.2 . . ?
C18 C17 H8 120.2 . . ?
C17 C18 C13 120.3(2) . . ?
C17 C18 C5 124.6(2) . . ?
C13 C18 C5 115.2(2) . . ?
O3 C19 C20 119.4(2) . . ?
O3 C19 C6 119.7(2) . . ?
C20 C19 C6 120.78(18) . . ?
C25 C20 C21 117.5(2) . . ?
C25 C20 C19 115.59(19) . . ?
C21 C20 C19 126.9(2) . . ?
C22 C21 C20 121.4(2) . . ?
C22 C21 Cl2 116.50(17) . . ?
C20 C21 Cl2 122.05(18) . . ?
C23 C22 C21 118.9(2) . . ?
C23 C22 H9 120.6 . . ?
C21 C22 H9 120.6 . . ?
C24 C23 C22 121.6(2) . . ?
C24 C23 Cl1 119.41(19) . . ?
C22 C23 Cl1 119.00(19) . . ?
C23 C24 C25 118.3(2) . . ?
C23 C24 H10 120.8 . . ?
C25 C24 H10 120.8 . . ?
C24 C25 C20 122.3(2) . . ?
C24 C25 H11 118.8 . . ?
C20 C25 H11 118.8 . . ?
C8 C26 C27 119.7(3) . . ?
C8 C26 H13 120.2 . . ?
C27 C26 H13 120.2 . . ?
C11 C27 C26 121.2(3) . . ?
C11 C27 H16 119.4 . . ?
C26 C27 H16 119.4 . . ?
O4 C28 N4 122.3(2) . . ?
O4 C28 C29 122.6(2) . . ?
N4 C28 C29 115.1(2) . . ?
C34 C29 C30 119.6(2) . . ?
C34 C29 C28 121.3(2) . . ?
C30 C29 C28 119.1(2) . . ?
C31 C30 C29 119.8(3) . . ?
C31 C30 H17 120.1 . . ?
C29 C30 H17 120.1 . . ?
C30 C31 C32 120.8(3) . . ?
C30 C31 H18 119.6 . . ?
C32 C31 H18 119.6 . . ?
C33 C32 C31 120.6(3) . . ?
C33 C32 H19 119.7 . . ?
C31 C32 H19 119.7 . . ?
C32 C33 C34 118.9(3) . . ?
C32 C33 H20 120.6 . . ?
C34 C33 H20 120.6 . . ?
C29 C34 C33 120.3(2) . . ?
C29 C34 C7 115.3(2) . . ?
C33 C34 C7 124.4(2) . . ?
C4 C35 C36 119.6(3) . . ?
C4 C35 H21 120.2 . . ?
C36 C35 H21 120.2 . . ?
C1 C36 C35 121.1(3) . . ?
C1 C36 H22 119.5 . . ?
C35 C36 H22 119.5 . . ?
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 C23 1.732(3) . ?
Cl2 C21 1.736(2) . ?
O1 C5 1.372(3) . ?
O1 C6 1.418(3) . ?
O2 C7 1.378(3) . ?
O2 C6 1.410(3) . ?
O3 C19 1.204(3) . ?
O4 C28 1.221(3) . ?
O5 C12 1.232(3) . ?
N1 C12 1.386(3) . ?
N1 N2 1.389(3) . ?
N1 C4 1.438(3) . ?
N2 C5 1.270(3) . ?
N3 C7 1.280(3) . ?
N3 N4 1.383(3) . ?
N4 C28 1.394(3) . ?
N4 C8 1.442(3) . ?
C1 C36 1.362(5) . ?
C1 C2 1.368(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.388(4) . ?
C2 H3 0.9300 . ?
C3 C4 1.387(4) . ?
C3 H4 0.9300 . ?
C4 C35 1.379(4) . ?
C5 C18 1.443(3) . ?
C6 C19 1.538(3) . ?
C6 H12 0.9800 . ?
C7 C34 1.434(3) . ?
C8 C26 1.380(4) . ?
C8 C9 1.381(4) . ?
C9 C10 1.384(4) . ?
C9 H14 0.9300 . ?
C10 C11 1.360(5) . ?
C10 H15 0.9300 . ?
C11 C27 1.367(5) . ?
C11 H2 0.9300 . ?
C12 C13 1.462(3) . ?
C13 C18 1.396(3) . ?
C13 C14 1.398(3) . ?
C14 C15 1.371(4) . ?
C14 H5 0.9300 . ?
C15 C16 1.386(4) . ?
C15 H6 0.9300 . ?
C16 C17 1.377(4) . ?
C16 H7 0.9300 . ?
C17 C18 1.394(3) . ?
C17 H8 0.9300 . ?
C19 C20 1.504(3) . ?
C20 C25 1.392(3) . ?
C20 C21 1.393(3) . ?
C21 C22 1.386(3) . ?
C22 C23 1.385(3) . ?
C22 H9 0.9300 . ?
C23 C24 1.376(4) . ?
C24 C25 1.383(4) . ?
C24 H10 0.9300 . ?
C25 H11 0.9300 . ?
C26 C27 1.388(4) . ?
C26 H13 0.9300 . ?
C27 H16 0.9300 . ?
C28 C29 1.473(4) . ?
C29 C34 1.391(4) . ?
C29 C30 1.398(4) . ?
C30 C31 1.367(4) . ?
C30 H17 0.9300 . ?
C31 C32 1.388(4) . ?
C31 H18 0.9300 . ?
C32 C33 1.380(4) . ?
C32 H19 0.9300 . ?
C33 C34 1.404(3) . ?
C33 H20 0.9300 . ?
C35 C36 1.388(4) . ?
C35 H21 0.9300 . ?
C36 H22 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H14 O4 0.93 2.18 2.764(4) 120.2 .
C9 H14 Cl2 0.93 2.91 3.638(4) 135.8 2_666
C6 H12 Cl2 0.98 2.56 3.138(3) 117.6 .
C3 H4 O5 0.93 2.30 2.786(4) 112.1 .
C9 H14 O4 0.93 2.18 2.764(4) 120.2 .
C9 H14 Cl2 0.93 2.91 3.638(4) 135.8 2_666
C6 H12 Cl2 0.98 2.56 3.138(3) 117.6 .
C3 H4 O5 0.93 2.30 2.786(4) 112.1 .
C3 H4 O5 0.93 2.30 2.786(4) 112.1 .
C6 H12 Cl2 0.98 2.56 3.138(3) 117.6 .
C9 H14 Cl2 0.93 2.91 3.638(4) 135.8 2_666
C9 H14 O4 0.93 2.18 2.764(4) 120.2 .
C3 H4 O5 0.93 2.30 2.786(4) 112.1 .
C6 H12 Cl2 0.98 2.56 3.138(3) 117.6 .
C9 H14 Cl2 0.93 2.91 3.638(4) 135.8 2_666
C9 H14 O4 0.93 2.18 2.764(4) 120.2 .
C3 H4 O5 0.93 2.30 2.786(4) 112.1 .
C6 H12 Cl2 0.98 2.56 3.138(3) 117.6 .
C9 H14 Cl2 0.93 2.91 3.638(4) 135.8 2_666
C9 H14 O4 0.93 2.18 2.764(4) 120.2 .
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
C12 N1 N2 C5 7.9(3) . . . . ?
C4 N1 N2 C5 -176.1(2) . . . . ?
C7 N3 N4 C28 -0.4(3) . . . . ?
C7 N3 N4 C8 178.44(19) . . . . ?
C36 C1 C2 C3 1.0(6) . . . . ?
C1 C2 C3 C4 0.8(6) . . . . ?
C2 C3 C4 C35 -2.7(5) . . . . ?
C2 C3 C4 N1 -179.4(3) . . . . ?
C12 N1 C4 C35 153.1(2) . . . . ?
N2 N1 C4 C35 -22.9(3) . . . . ?
C12 N1 C4 C3 -30.2(4) . . . . ?
N2 N1 C4 C3 153.8(3) . . . . ?
N1 N2 C5 O1 -179.72(18) . . . . ?
N1 N2 C5 C18 -0.2(3) . . . . ?
C6 O1 C5 N2 12.5(3) . . . . ?
C6 O1 C5 C18 -167.14(19) . . . . ?
C7 O2 C6 O1 83.1(2) . . . . ?
C7 O2 C6 C19 -160.25(17) . . . . ?
C5 O1 C6 O2 -151.77(18) . . . . ?
C5 O1 C6 C19 93.8(2) . . . . ?
N4 N3 C7 O2 -179.36(18) . . . . ?
N4 N3 C7 C34 -1.7(3) . . . . ?
C6 O2 C7 N3 -7.8(3) . . . . ?
C6 O2 C7 C34 174.23(18) . . . . ?
N3 N4 C8 C26 17.2(3) . . . . ?
C28 N4 C8 C26 -164.1(2) . . . . ?
N3 N4 C8 C9 -159.1(2) . . . . ?
C28 N4 C8 C9 19.7(4) . . . . ?
C26 C8 C9 C10 0.4(5) . . . . ?
N4 C8 C9 C10 176.6(3) . . . . ?
C8 C9 C10 C11 -1.1(6) . . . . ?
C9 C10 C11 C27 0.7(6) . . . . ?
N2 N1 C12 O5 170.5(2) . . . . ?
C4 N1 C12 O5 -5.2(4) . . . . ?
N2 N1 C12 C13 -10.4(3) . . . . ?
C4 N1 C12 C13 174.0(2) . . . . ?
O5 C12 C13 C18 -175.0(2) . . . . ?
N1 C12 C13 C18 5.8(3) . . . . ?
O5 C12 C13 C14 4.9(4) . . . . ?
N1 C12 C13 C14 -174.3(2) . . . . ?
C18 C13 C14 C15 -0.5(4) . . . . ?
C12 C13 C14 C15 179.5(2) . . . . ?
C13 C14 C15 C16 -0.6(4) . . . . ?
C14 C15 C16 C17 1.4(5) . . . . ?
C15 C16 C17 C18 -1.1(4) . . . . ?
C16 C17 C18 C13 0.0(4) . . . . ?
C16 C17 C18 C5 180.0(2) . . . . ?
C14 C13 C18 C17 0.8(3) . . . . ?
C12 C13 C18 C17 -179.3(2) . . . . ?
C14 C13 C18 C5 -179.2(2) . . . . ?
C12 C13 C18 C5 0.8(3) . . . . ?
N2 C5 C18 C17 176.1(2) . . . . ?
O1 C5 C18 C17 -4.3(3) . . . . ?
N2 C5 C18 C13 -3.9(3) . . . . ?
O1 C5 C18 C13 175.68(19) . . . . ?
O2 C6 C19 O3 -123.4(2) . . . . ?
O1 C6 C19 O3 -7.2(3) . . . . ?
O2 C6 C19 C20 53.1(2) . . . . ?
O1 C6 C19 C20 169.24(18) . . . . ?
O3 C19 C20 C25 32.9(3) . . . . ?
C6 C19 C20 C25 -143.6(2) . . . . ?
O3 C19 C20 C21 -145.5(3) . . . . ?
C6 C19 C20 C21 38.0(3) . . . . ?
C25 C20 C21 C22 0.2(3) . . . . ?
C19 C20 C21 C22 178.6(2) . . . . ?
C25 C20 C21 Cl2 -177.30(18) . . . . ?
C19 C20 C21 Cl2 1.1(3) . . . . ?
C20 C21 C22 C23 0.4(4) . . . . ?
Cl2 C21 C22 C23 178.01(19) . . . . ?
C21 C22 C23 C24 -0.4(4) . . . . ?
C21 C22 C23 Cl1 179.49(18) . . . . ?
C22 C23 C24 C25 -0.2(4) . . . . ?
Cl1 C23 C24 C25 179.96(19) . . . . ?
C23 C24 C25 C20 0.8(4) . . . . ?
C21 C20 C25 C24 -0.8(4) . . . . ?
C19 C20 C25 C24 -179.4(2) . . . . ?
C9 C8 C26 C27 0.6(4) . . . . ?
N4 C8 C26 C27 -175.7(3) . . . . ?
C10 C11 C27 C26 0.3(6) . . . . ?
C8 C26 C27 C11 -0.9(5) . . . . ?
N3 N4 C28 O4 -175.9(3) . . . . ?
C8 N4 C28 O4 5.4(4) . . . . ?
N3 N4 C28 C29 2.9(3) . . . . ?
C8 N4 C28 C29 -175.8(2) . . . . ?
O4 C28 C29 C34 175.1(3) . . . . ?
N4 C28 C29 C34 -3.6(3) . . . . ?
O4 C28 C29 C30 -4.3(4) . . . . ?
N4 C28 C29 C30 176.9(2) . . . . ?
C34 C29 C30 C31 -0.8(4) . . . . ?
C28 C29 C30 C31 178.7(3) . . . . ?
C29 C30 C31 C32 -0.4(5) . . . . ?
C30 C31 C32 C33 0.8(5) . . . . ?
C31 C32 C33 C34 0.0(4) . . . . ?
C30 C29 C34 C33 1.6(4) . . . . ?
C28 C29 C34 C33 -177.8(2) . . . . ?
C30 C29 C34 C7 -178.6(2) . . . . ?
C28 C29 C34 C7 2.0(3) . . . . ?
C32 C33 C34 C29 -1.2(4) . . . . ?
C32 C33 C34 C7 179.0(2) . . . . ?
N3 C7 C34 C29 0.8(3) . . . . ?
O2 C7 C34 C29 178.55(19) . . . . ?
N3 C7 C34 C33 -179.4(2) . . . . ?
O2 C7 C34 C33 -1.7(3) . . . . ?
C3 C4 C35 C36 2.8(4) . . . . ?
N1 C4 C35 C36 179.5(2) . . . . ?
C2 C1 C36 C35 -1.0(5) . . . . ?
C4 C35 C36 C1 -0.9(5) . . . . ?
