#------------------------------------------------------------------------------
#$Date: 2023-09-05 23:23:40 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286195 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/95/7159516.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_7159516
loop_
_publ_author_name
'Prieto, Elena'
'Martín, Jorge D'
'Nieto, Javier'
'Andrés, Celia'
_publ_section_title
;
 Enantioselective synthesis of 3-hydroxy- and
 3-amino-3-alkynyl-2-oxindoles by the dimethylzinc-mediated addition of
 terminal alkynes to isatins and isatin-derived ketimines.
;
_journal_issue                   34
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6940
_journal_page_last               6948
_journal_paper_doi               10.1039/d3ob01023f
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H20 Cl4 N2 O2'
_chemical_formula_sum            'C30 H20 Cl4 N2 O2'
_chemical_formula_weight         582.28
_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             2021-04-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-07-19 deposited with the CCDC.	2023-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.147(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.1758(3)
_cell_length_b                   5.34020(10)
_cell_length_c                   21.8778(6)
_cell_measurement_reflns_used    3548
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      74.6930
_cell_measurement_theta_min      3.8310
_cell_volume                     1395.68(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00   1.00   1.00   13.82    --  -41.06 122.00-123.00   90
  2  ω    -70.00 -44.00   1.00   13.82    --  -41.06 178.00-120.00   26
  3  ω   -111.00  -8.00   1.00   13.82    --  -41.06 -77.00 150.00  103
  4  ω    -68.00 -39.00   1.00   13.82    --  -41.06 178.00 150.00   29
  5  ω   -100.00 -17.00   1.00   13.82    --  -41.06 -57.00  30.00   83
  6  ω     75.00 134.00   1.00   55.29    --  110.01 -30.00   0.00   59
  7  ω     35.00  60.00   1.00   55.29    --  110.01 -30.00   0.00   25
  8  ω     38.00 134.00   1.00   55.29    --  110.01 -45.00 -90.00   96
  9  ω     65.00 108.00   1.00   55.29    --  110.01-125.00  60.00   43
 10  ω     47.00 116.00   1.00   55.29    --  110.01-125.00 -90.00   69
 11  ω     48.00 115.00   1.00   55.29    --  110.01 -30.00  90.00   67
 12  ω    119.00 165.00   1.00   55.29    --  110.01  30.00-120.00   46
 13  ω     34.00  59.00   1.00   55.29    --  110.01 -94.00 -90.00   25
 14  ω     76.00 110.00   1.00   55.29    --  110.01 -94.00 -90.00   34
 15  ω    102.00 127.00   1.00   55.29    --  110.01 125.00 150.00   25
 16  ω     88.00 114.00   1.00   55.29    --  110.01-122.00 154.00   26
 17  ω    107.00 175.00   1.00   55.29    --  110.01  45.00  30.00   68
 18  ω     79.00 145.00   1.00   55.29    --  110.01 151.00  37.00   66
 19  ω     36.00 141.00   1.00   55.29    --  110.01 -77.00  60.00  105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0352677000
_diffrn_orient_matrix_UB_12      0.2769990000
_diffrn_orient_matrix_UB_13      0.0004528000
_diffrn_orient_matrix_UB_21      0.1226958000
_diffrn_orient_matrix_UB_22      0.0755010000
_diffrn_orient_matrix_UB_23      0.0245245000
_diffrn_orient_matrix_UB_31      0.0178146000
_diffrn_orient_matrix_UB_32      0.0292937000
_diffrn_orient_matrix_UB_33      -0.0674591000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9628
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.059
_diffrn_reflns_theta_min         3.700
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.102
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.539
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       needle
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.411
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1827 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5556
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0457
_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)+(0.0452P)²+0.4413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1205
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                4885
_reflns_number_total             5556
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01023f2.cif
_cod_data_source_block           el1345b
_cod_depositor_comments
'Adding full bibliography for 7159515--7159516.cif.'
_cod_database_code               7159516
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C30 H20 Cl4 N2 O2'
_chemical_oxdiff_usercomment     colorless
_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   0.837
_shelx_estimated_absorpt_t_min   0.283
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C10, C11, C12, C13, C14, C15
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
4.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
4.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14),
 C24(H24), C26(H26), C27(H27), C28(H28), C31(H31), C33(H33), C35(H35)
4.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.332
_oxdiff_exptl_absorpt_empirical_full_min 0.696
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
Cl1 Cl 0.11707(13) 0.4642(5) 0.08891(10) 0.1170(7) Uani 1 1 d . . . . .
Cl2 Cl 0.53305(14) 0.8517(4) 0.09841(7) 0.1006(6) Uani 1 1 d . . . . .
Cl3 Cl 0.94488(16) 1.0398(4) 0.13684(9) 0.1141(7) Uani 1 1 d . . . . .
Cl4 Cl 0.99056(10) 0.3282(3) 0.31280(7) 0.0807(4) Uani 1 1 d . . . . .
O1 O 0.5856(2) 0.3921(5) 0.21311(14) 0.0586(7) Uani 1 1 d . . . . .
O2 O 0.8767(3) -0.1437(8) 0.49426(18) 0.0860(11) Uani 1 1 d . . . . .
N1 N 0.4219(3) 0.6156(6) 0.19960(15) 0.0463(7) Uani 1 1 d . . . . .
N2 N 0.6495(3) 0.9097(6) 0.26907(17) 0.0518(8) Uani 1 1 d . . . . .
H2 H 0.638365 1.068633 0.269897 0.062 Uiso 1 1 calc R U . . .
C1 C 0.5273(3) 0.5550(7) 0.22934(17) 0.0451(8) Uani 1 1 d . . . . .
C2 C 0.5622(3) 0.7442(7) 0.28403(18) 0.0444(8) Uani 1 1 d . . . . .
C3 C 0.4550(3) 0.8906(7) 0.28106(17) 0.0450(8) Uani 1 1 d . . . . .
C4 C 0.4299(4) 1.0755(9) 0.3196(2) 0.0582(10) Uani 1 1 d . . . . .
H4 H 0.482512 1.129608 0.353675 0.070 Uiso 1 1 calc R U . . .
C5 C 0.3230(4) 1.1799(10) 0.3060(3) 0.0690(13) Uani 1 1 d . . . . .
H5 H 0.304000 1.306405 0.331272 0.083 Uiso 1 1 calc R U . . .
C6 C 0.2454(4) 1.0988(10) 0.2560(2) 0.0678(12) Uani 1 1 d . . . . .
H6 H 0.175047 1.173291 0.247575 0.081 Uiso 1 1 calc R U . . .
C7 C 0.2695(3) 0.9079(9) 0.2175(2) 0.0580(10) Uani 1 1 d . . . . .
H7 H 0.216223 0.849988 0.184237 0.070 Uiso 1 1 calc R U . . .
C8 C 0.3763(3) 0.8076(7) 0.23088(17) 0.0433(7) Uani 1 1 d . . . . .
C9 C 0.3687(4) 0.4909(8) 0.1424(2) 0.0564(10) Uani 1 1 d . . . . .
H9A H 0.308390 0.386570 0.151065 0.068 Uiso 1 1 calc R U . . .
H9B H 0.423099 0.382006 0.128774 0.068 Uiso 1 1 calc R U . . .
C10 C 0.3223(4) 0.6677(9) 0.09007(19) 0.0571(10) Uani 1 1 d . U . . .
C11 C 0.2090(5) 0.6675(12) 0.0624(2) 0.0801(15) Uani 1 1 d . U . . .
C12 C 0.1662(8) 0.826(2) 0.0139(3) 0.128(3) Uani 1 1 d . U . . .
H12 H 0.090448 0.820453 -0.004008 0.153 Uiso 1 1 calc R U . . .
C13 C 0.2352(11) 0.990(2) -0.0077(4) 0.147(4) Uani 1 1 d . U . . .
H13 H 0.206238 1.098577 -0.040146 0.176 Uiso 1 1 calc R U . . .
C14 C 0.3481(9) 0.9979(17) 0.0183(3) 0.127(3) Uani 1 1 d . U . . .
H14 H 0.395156 1.109857 0.003313 0.153 Uiso 1 1 calc R U . . .
C15 C 0.3906(5) 0.8371(11) 0.0668(2) 0.0749(13) Uani 1 1 d . U . . .
C21 C 0.5979(3) 0.6129(7) 0.3434(2) 0.0508(9) Uani 1 1 d . . . . .
C22 C 0.6277(4) 0.5038(8) 0.39136(19) 0.0542(9) Uani 1 1 d . . . . .
C23 C 0.6699(3) 0.3556(8) 0.44559(18) 0.0542(9) Uani 1 1 d . . . . .
C24 C 0.7522(4) 0.1775(9) 0.4417(2) 0.0589(10) Uani 1 1 d . . . . .
H24 H 0.778002 0.157396 0.404694 0.071 Uiso 1 1 calc R U . . .
C25 C 0.7955(4) 0.0304(10) 0.4930(2) 0.0650(11) Uani 1 1 d . . . . .
C26 C 0.7561(5) 0.0596(13) 0.5470(3) 0.0871(17) Uani 1 1 d . . . . .
H26 H 0.785426 -0.037313 0.581659 0.105 Uiso 1 1 calc R U . . .
C27 C 0.6741(6) 0.2295(16) 0.5504(3) 0.104(2) Uani 1 1 d . . . . .
H27 H 0.646825 0.243705 0.587157 0.124 Uiso 1 1 calc R U . . .
C28 C 0.6303(5) 0.3820(12) 0.5002(2) 0.0816(15) Uani 1 1 d . . . . .
H28 H 0.575369 0.499744 0.503365 0.098 Uiso 1 1 calc R U . . .
C29 C 0.9237(6) -0.1719(16) 0.4416(3) 0.106(2) Uani 1 1 d . . . . .
H29A H 0.865718 -0.207626 0.406281 0.159 Uiso 1 1 calc R U . . .
H29B H 0.976437 -0.307414 0.447964 0.159 Uiso 1 1 calc R U . . .
H29C H 0.961283 -0.020016 0.434299 0.159 Uiso 1 1 calc R U . . .
C30 C 0.7492(3) 0.8269(8) 0.25361(18) 0.0480(8) Uani 1 1 d . . . . .
C31 C 0.7917(4) 0.9534(8) 0.2078(2) 0.0556(9) Uani 1 1 d . . . . .
H31 H 0.751932 1.085155 0.186210 0.067 Uiso 1 1 calc R U . . .
C32 C 0.8936(4) 0.8815(10) 0.1948(2) 0.0670(12) Uani 1 1 d . . . . .
C33 C 0.9570(4) 0.6889(10) 0.2253(2) 0.0660(12) Uani 1 1 d . . . . .
H33 H 1.025720 0.644469 0.215908 0.079 Uiso 1 1 calc R U . . .
C34 C 0.9133(3) 0.5661(9) 0.2703(2) 0.0586(10) Uani 1 1 d . . . . .
C35 C 0.8105(3) 0.6263(8) 0.2841(2) 0.0541(9) Uani 1 1 d . . . . .
H35 H 0.782133 0.533778 0.313588 0.065 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'
Cl Cl 0.3639 0.7018 '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'
O O 0.0492 0.0322 '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
1 0 -5 0.0348
-1 0 5 0.0168
0 1 0 0.2135
0 -1 0 0.1975
5 0 1 0.0141
-5 0 -1 0.0311
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
C25 O2 C29 118.2(4) . . ?
C1 N1 C8 111.4(3) . . ?
C1 N1 C9 121.6(3) . . ?
C8 N1 C9 127.0(3) . . ?
C2 N2 H2 117.8 . . ?
C30 N2 H2 117.8 . . ?
C30 N2 C2 124.4(3) . . ?
O1 C1 N1 125.4(4) . . ?
O1 C1 C2 126.8(3) . . ?
N1 C1 C2 107.7(3) . . ?
N2 C2 C1 108.7(3) . . ?
N2 C2 C3 109.6(3) . . ?
C3 C2 C1 101.4(3) . . ?
C21 C2 N2 112.5(3) . . ?
C21 C2 C1 111.1(3) . . ?
C21 C2 C3 113.0(3) . . ?
C4 C3 C2 129.7(4) . . ?
C4 C3 C8 121.1(4) . . ?
C8 C3 C2 109.2(3) . . ?
C3 C4 H4 121.1 . . ?
C3 C4 C5 117.8(4) . . ?
C5 C4 H4 121.1 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(4) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.5(4) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 121.4 . . ?
C8 C7 C6 117.2(4) . . ?
C8 C7 H7 121.4 . . ?
C3 C8 N1 110.0(3) . . ?
C3 C8 C7 121.4(4) . . ?
C7 C8 N1 128.5(4) . . ?
N1 C9 H9A 108.8 . . ?
N1 C9 H9B 108.8 . . ?
N1 C9 C10 114.0(4) . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C11 C10 C9 121.6(5) . . ?
C15 C10 C9 121.5(4) . . ?
C15 C10 C11 116.9(5) . . ?
C10 C11 Cl1 120.2(5) . . ?
C12 C11 Cl1 117.9(6) . . ?
C12 C11 C10 121.9(7) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.7(8) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.5(7) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.4(8) . . ?
C15 C14 H14 120.3 . . ?
C10 C15 Cl2 120.3(4) . . ?
C14 C15 Cl2 118.2(6) . . ?
C14 C15 C10 121.5(7) . . ?
C22 C21 C2 179.2(5) . . ?
C21 C22 C23 174.0(5) . . ?
C24 C23 C22 118.1(4) . . ?
C28 C23 C22 122.0(4) . . ?
C28 C23 C24 119.8(4) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.1(4) . . ?
C25 C24 H24 119.9 . . ?
O2 C25 C24 124.6(5) . . ?
O2 C25 C26 115.9(5) . . ?
C26 C25 C24 119.5(5) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.4(5) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 119.3 . . ?
C26 C27 C28 121.4(5) . . ?
C28 C27 H27 119.3 . . ?
C23 C28 C27 118.7(5) . . ?
C23 C28 H28 120.7 . . ?
C27 C28 H28 120.7 . . ?
O2 C29 H29A 109.5 . . ?
O2 C29 H29B 109.5 . . ?
O2 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N2 C30 C35 122.4(4) . . ?
C31 C30 N2 119.0(4) . . ?
C31 C30 C35 118.6(4) . . ?
C30 C31 H31 120.4 . . ?
C32 C31 C30 119.3(4) . . ?
C32 C31 H31 120.4 . . ?
C31 C32 Cl3 118.7(4) . . ?
C33 C32 Cl3 118.0(4) . . ?
C33 C32 C31 123.3(4) . . ?
C32 C33 H33 121.8 . . ?
C34 C33 C32 116.4(4) . . ?
C34 C33 H33 121.8 . . ?
C33 C34 Cl4 119.2(3) . . ?
C33 C34 C35 122.7(4) . . ?
C35 C34 Cl4 118.1(4) . . ?
C30 C35 H35 120.1 . . ?
C34 C35 C30 119.7(4) . . ?
C34 C35 H35 120.1 . . ?
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 C11 1.738(7) . ?
Cl2 C15 1.740(6) . ?
Cl3 C32 1.737(5) . ?
Cl4 C34 1.740(5) . ?
O1 C1 1.218(5) . ?
O2 C25 1.354(6) . ?
O2 C29 1.389(7) . ?
N1 C1 1.362(5) . ?
N1 C8 1.405(5) . ?
N1 C9 1.455(5) . ?
N2 H2 0.8600 . ?
N2 C2 1.467(5) . ?
N2 C30 1.394(5) . ?
C1 C2 1.561(5) . ?
C2 C3 1.512(5) . ?
C2 C21 1.466(6) . ?
C3 C4 1.371(6) . ?
C3 C8 1.383(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.395(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.370(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.389(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.384(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.507(6) . ?
C10 C11 1.395(7) . ?
C10 C15 1.391(7) . ?
C11 C12 1.378(10) . ?
C12 H12 0.9300 . ?
C12 C13 1.363(14) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(14) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(9) . ?
C21 C22 1.194(6) . ?
C22 C23 1.436(6) . ?
C23 C24 1.396(6) . ?
C23 C28 1.380(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.387(6) . ?
C25 C26 1.369(8) . ?
C26 H26 0.9300 . ?
C26 C27 1.362(9) . ?
C27 H27 0.9300 . ?
C27 C28 1.388(8) . ?
C28 H28 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.388(6) . ?
C30 C35 1.399(6) . ?
C31 H31 0.9300 . ?
C31 C32 1.380(6) . ?
C32 C33 1.379(7) . ?
C33 H33 0.9300 . ?
C33 C34 1.372(7) . ?
C34 C35 1.381(6) . ?
C35 H35 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
Cl1 C11 C12 C13 179.1(7) . . . . ?
Cl3 C32 C33 C34 -179.3(4) . . . . ?
Cl4 C34 C35 C30 176.0(3) . . . . ?
O1 C1 C2 N2 65.6(5) . . . . ?
O1 C1 C2 C3 -179.0(4) . . . . ?
O1 C1 C2 C21 -58.7(5) . . . . ?
O2 C25 C26 C27 -179.8(6) . . . . ?
N1 C1 C2 N2 -110.0(3) . . . . ?
N1 C1 C2 C3 5.4(4) . . . . ?
N1 C1 C2 C21 125.7(3) . . . . ?
N1 C9 C10 C11 -120.9(5) . . . . ?
N1 C9 C10 C15 59.8(6) . . . . ?
N2 C2 C3 C4 -69.4(5) . . . . ?
N2 C2 C3 C8 111.5(4) . . . . ?
N2 C30 C31 C32 176.3(4) . . . . ?
N2 C30 C35 C34 -174.6(4) . . . . ?
C1 N1 C8 C3 3.7(4) . . . . ?
C1 N1 C8 C7 -175.4(4) . . . . ?
C1 N1 C9 C10 -128.1(4) . . . . ?
C1 C2 C3 C4 175.8(4) . . . . ?
C1 C2 C3 C8 -3.2(4) . . . . ?
C2 N2 C30 C31 141.8(4) . . . . ?
C2 N2 C30 C35 -40.6(6) . . . . ?
C2 C3 C4 C5 -179.9(4) . . . . ?
C2 C3 C8 N1 0.1(4) . . . . ?
C2 C3 C8 C7 179.3(4) . . . . ?
C3 C4 C5 C6 0.4(7) . . . . ?
C4 C3 C8 N1 -179.0(4) . . . . ?
C4 C3 C8 C7 0.1(6) . . . . ?
C4 C5 C6 C7 1.0(8) . . . . ?
C5 C6 C7 C8 -1.7(7) . . . . ?
C6 C7 C8 N1 -179.8(4) . . . . ?
C6 C7 C8 C3 1.2(6) . . . . ?
C8 N1 C1 O1 178.6(4) . . . . ?
C8 N1 C1 C2 -5.7(4) . . . . ?
C8 N1 C9 C10 51.2(6) . . . . ?
C8 C3 C4 C5 -0.9(6) . . . . ?
C9 N1 C1 O1 -2.0(6) . . . . ?
C9 N1 C1 C2 173.7(3) . . . . ?
C9 N1 C8 C3 -175.7(4) . . . . ?
C9 N1 C8 C7 5.3(6) . . . . ?
C9 C10 C11 Cl1 1.2(7) . . . . ?
C9 C10 C11 C12 -179.0(6) . . . . ?
C9 C10 C15 Cl2 -0.7(6) . . . . ?
C9 C10 C15 C14 179.3(6) . . . . ?
C10 C11 C12 C13 -0.7(11) . . . . ?
C11 C10 C15 Cl2 179.9(4) . . . . ?
C11 C10 C15 C14 -0.1(8) . . . . ?
C11 C12 C13 C14 0.6(14) . . . . ?
C12 C13 C14 C15 -0.3(14) . . . . ?
C13 C14 C15 Cl2 -180.0(7) . . . . ?
C13 C14 C15 C10 0.0(12) . . . . ?
C15 C10 C11 Cl1 -179.4(4) . . . . ?
C15 C10 C11 C12 0.4(8) . . . . ?
C21 C2 C3 C4 56.9(5) . . . . ?
C21 C2 C3 C8 -122.2(4) . . . . ?
C22 C23 C24 C25 179.9(4) . . . . ?
C22 C23 C28 C27 179.1(6) . . . . ?
C23 C24 C25 O2 -178.7(5) . . . . ?
C23 C24 C25 C26 0.7(8) . . . . ?
C24 C23 C28 C27 0.1(9) . . . . ?
C24 C25 C26 C27 0.7(10) . . . . ?
C25 C26 C27 C28 -1.7(12) . . . . ?
C26 C27 C28 C23 1.3(11) . . . . ?
C28 C23 C24 C25 -1.1(7) . . . . ?
C29 O2 C25 C24 2.7(9) . . . . ?
C29 O2 C25 C26 -176.8(7) . . . . ?
C30 N2 C2 C1 -54.7(5) . . . . ?
C30 N2 C2 C3 -164.6(4) . . . . ?
C30 N2 C2 C21 68.8(5) . . . . ?
C30 C31 C32 Cl3 179.4(4) . . . . ?
C30 C31 C32 C33 -0.3(8) . . . . ?
C31 C30 C35 C34 2.9(6) . . . . ?
C31 C32 C33 C34 0.5(8) . . . . ?
C32 C33 C34 Cl4 -177.7(4) . . . . ?
C32 C33 C34 C35 1.2(8) . . . . ?
C33 C34 C35 C30 -2.9(7) . . . . ?
C35 C30 C31 C32 -1.4(6) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.9994 -0.0001 -4.9998 -0.0375 -0.0000 0.3551
-0.9994 0.0001 4.9998 0.0375 0.0000 -0.3551
0.0003 1.0004 -0.0016 0.2771 0.0755 0.0294
-0.0003 -1.0004 0.0016 -0.2771 -0.0755 -0.0294
5.0037 0.0005 1.0021 -0.1759 0.6385 0.0216
-5.0037 -0.0005 -1.0021 0.1759 -0.6385 -0.0216
