#------------------------------------------------------------------------------
#$Date: 2021-12-03 22:38:35 +0200 (Fri, 03 Dec 2021) $
#$Revision: 271021 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/91/4519140.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_4519140
loop_
_publ_author_name
'Lv, Mingjun'
'Li, Xiaoxun'
_publ_section_title
;
 Ni(II)-Catalyzed Asymmetric Nitration of Oxindoles: Construction of
 Cipargamin Analogues
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              14829
_journal_page_last               14835
_journal_paper_doi               10.1021/acscatal.1c04460
_journal_year                    2021
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C19 H15 Cl2 N3 O, C3 H8 O'
_chemical_formula_sum            'C22 H23 Cl2 N3 O2'
_chemical_formula_weight         432.33
_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
_audit_creation_date             2021-01-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.962(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.7747(3)
_cell_length_b                   7.5306(3)
_cell_length_c                   14.5872(4)
_cell_measurement_reflns_used    4463
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.2330
_cell_measurement_theta_min      3.1140
_cell_volume                     1037.35(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     97.00 149.00   1.00    0.31    --  106.49  77.00 -90.00   52
  2  ω    153.00 178.00   1.00    0.31    --  106.49  77.00 -90.00   25
  3  ω     95.00 176.00   1.00    0.31    --  106.49  26.00-121.00   81
  4  ω     56.00  89.00   1.00    0.10    --   48.32  26.00-121.00   33
  5  ω    -25.00  24.00   1.00    0.10    --   48.32 -19.00 -60.00   49
  6  ω     37.00  68.00   1.00    0.31    --  106.49 -77.00-180.00   31
  7  ω     72.00 102.00   1.00    0.31    --  106.49 -77.00-180.00   30
  8  ω     40.00  66.00   1.00    0.31    --  106.49 -57.00 -60.00   26
  9  ω     -5.00  24.00   1.00    0.10    --   48.32 -26.00  75.00   29
 10  ω     34.00  63.00   1.00    0.31    --  106.49 -57.00 150.00   29
 11  ω    129.00 165.00   1.00    0.31    --  106.49 125.00  60.00   36
 12  ω     95.00 127.00   1.00    0.31    --  106.49 125.00  60.00   32
 13  ω     95.00 177.00   1.00    0.31    --  106.49 125.00 -90.00   82
 14  ω     37.00  63.00   1.00    0.31    --  106.49-125.00 -60.00   26
 15  ω     65.00 111.00   1.00    0.31    --  106.49-125.00 -60.00   46
 16  ω    -31.00  26.00   1.00    0.10    --  -48.32  26.00-121.00   57
 17  ω    -65.00 -14.00   1.00    0.31    --  -86.25  57.00 -60.00   51
 18  ω    -66.00 -14.00   1.00    0.31    --  -86.25  57.00  30.00   52
 19  ω    -38.00 -13.00   1.00    0.31    --  -86.25  38.00  60.00   25
 20  ω   -120.00 -37.00   1.00    0.10    --  -48.32 -26.00  75.00   83
 21  ω    -65.00 -26.00   1.00    0.10    --  -48.32 -77.00   0.00   39
 22  ω    -62.00 -28.00   1.00    0.10    --  -48.32 -77.00 -60.00   34
 23  ω   -106.00 -80.00   1.00    0.10    --  -48.32 -77.00   0.00   26
 24  ω   -152.00-127.00   1.00    0.31    --  -86.25 -80.00 -12.87   25
 25  ω   -159.00-120.00   1.00    0.31    --  -86.25 -77.00 -60.00   39
 26  ω   -118.00 -62.00   1.00    0.31    --  -86.25 -80.00 -12.87   56
 27  ω    -88.00 -63.00   1.00    0.31    --  -86.25 -77.00  30.00   25
 28  ω   -130.00 -62.00   1.00    0.31    --  -86.25 -80.00  17.72   68
 29  ω   -148.00-110.00   1.00    0.31    --  -86.25 -77.00  30.00   38
 30  ω   -122.00 -63.00   1.00    0.31    --  -86.25 -77.00   0.00   59
 31  ω   -107.00 -63.00   1.00    0.31    --  -86.25 -77.00 -60.00   44
 32  ω   -107.00 -64.00   1.00    0.31    --  -86.25 -76.00 -39.19   43
 33  ω   -148.00-122.00   1.00    0.31    --  -86.25 -76.00 -39.19   26
 34  ω   -151.00 -67.00   1.00    0.31    --  -86.25 -74.00  47.36   84
 35  ω   -131.00-106.00   1.00    0.31    --  -86.25 -26.00  75.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1098427000
_diffrn_orient_matrix_UB_12      0.0637906000
_diffrn_orient_matrix_UB_13      0.0897962000
_diffrn_orient_matrix_UB_21      0.1189726000
_diffrn_orient_matrix_UB_22      -0.0261891000
_diffrn_orient_matrix_UB_23      -0.0504319000
_diffrn_orient_matrix_UB_31      -0.0202497000
_diffrn_orient_matrix_UB_32      0.1925398000
_diffrn_orient_matrix_UB_33      -0.0366470000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10652
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         3.136
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    3.008
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1284 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.017(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3632
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0426
_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)+(0.0640P)²+0.0230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1158
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_full    0.948
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                3214
_reflns_number_total             3632
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c04460_si_003.cif
_cod_data_source_block           210126c
_cod_database_code               4519140
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         ClC
_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   0.864
_shelx_estimated_absorpt_t_min   0.840
_diffrn_oxdiff_digest_frames
;
01e8fa6637855b6523f2b725722352502301506717f
;
_diffrn_oxdiff_digest_hkl
;
0107d27859b773b68d32b93e2e8cc2fec01105
;
_reflns_odcompleteness_completeness 99.90
_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, All C(H,H,H,H,H,H) groups, All O(H,H) groups
2. Others
 Fixed Sof: H0A(0.6) H0AA(0.4) C1(0.6) H1A(0.6) C1A(0.4) H1AA(0.4) H2AA(0.6)
 H2AB(0.6) H2AC(0.6) H2BD(0.4) H2BE(0.4) H2BF(0.4) H3AA(0.6) H3AB(0.6)
 H3AC(0.6) H3BD(0.4) H3BE(0.4) H3BF(0.4)
3.a Ternary CH refined with riding coordinates:
 C15(H15), C1(H1A), C1A(H1AA)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), C4(H4), C6(H6), C9(H9), C19(H19), C20(H20), C22(H22)
3.d Tetrahedral OH refined with riding coordinates:
 O0A(H0A), O0A(H0AA)
3.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C2(H2AA,H2AB,H2AC), C2(H2BD,H2BE,H2BF), C3(H3AA,H3AB,
 H3AC), C3(H3BD,H3BE,H3BF)
;
_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 3.037
_oxdiff_exptl_absorpt_empirical_full_min 0.446
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 0.30605(16) 0.5090(2) 0.02280(7) 0.0766(4) Uani 1 1 d . . . . .
Cl2 Cl 0.71220(16) 0.5236(2) 0.95785(7) 0.0765(4) Uani 1 1 d . . . . .
O25 O 0.8741(3) 0.2426(4) 0.50200(17) 0.0420(6) Uani 1 1 d . . . . .
N1 N 0.4572(3) 0.3666(5) 0.3835(2) 0.0391(7) Uani 1 1 d . . . . .
H1 H 0.3952 0.2893 0.3893 0.047 Uiso 1 1 calc R . . . .
N2 N 0.7773(3) 0.5995(4) 0.5829(2) 0.0335(7) Uani 1 1 d . . . . .
H2 H 0.7886 0.6824 0.6247 0.040 Uiso 1 1 calc R . . . .
N3 N 0.9473(3) 0.2139(5) 0.6635(2) 0.0444(8) Uani 1 1 d . . . . .
H3 H 1.0169 0.1421 0.6669 0.053 Uiso 1 1 calc R . . . .
C4 C 0.5232(5) 0.6474(6) 0.1562(3) 0.0526(11) Uani 1 1 d . . . . .
H4 H 0.5425 0.7112 0.1064 0.063 Uiso 1 1 calc R . . . .
C5 C 0.4086(5) 0.5328(7) 0.1393(2) 0.0510(10) Uani 1 1 d . . . . .
C6 C 0.3733(4) 0.4364(6) 0.2096(3) 0.0466(9) Uani 1 1 d . . . . .
H6 H 0.2945 0.3624 0.1969 0.056 Uiso 1 1 calc R . . . .
C7 C 0.4613(4) 0.4546(5) 0.3011(2) 0.0374(8) Uani 1 1 d . . . . .
C8 C 0.5803(4) 0.5696(5) 0.3212(2) 0.0351(8) Uani 1 1 d . . . . .
C9 C 0.6090(4) 0.6667(6) 0.2475(3) 0.0450(9) Uani 1 1 d . . . . .
H9 H 0.6856 0.7444 0.2593 0.054 Uiso 1 1 calc R . . . .
C10 C 0.6470(3) 0.5482(5) 0.4212(2) 0.0327(7) Uani 1 1 d . . . . .
C11 C 0.5712(3) 0.4254(5) 0.4552(2) 0.0333(7) Uani 1 1 d . . . . .
C12 C 0.6052(3) 0.3575(5) 0.5548(2) 0.0364(8) Uani 1 1 d . . . . .
H12A H 0.5971 0.2291 0.5546 0.044 Uiso 1 1 calc R . . . .
H12B H 0.5390 0.4061 0.5875 0.044 Uiso 1 1 calc R . . . .
C13 C 0.7567(3) 0.4128(5) 0.6060(2) 0.0320(7) Uani 1 1 d . . . . .
C14 C 0.7847(4) 0.8345(5) 0.4702(3) 0.0385(8) Uani 1 1 d . . . . .
H14A H 0.6995 0.8883 0.4782 0.058 Uiso 1 1 calc GR . . . .
H14B H 0.7947 0.8603 0.4078 0.058 Uiso 1 1 calc GR . . . .
H14C H 0.8647 0.8810 0.5167 0.058 Uiso 1 1 calc GR . . . .
C15 C 0.7771(4) 0.6356(5) 0.4825(2) 0.0323(7) Uani 1 1 d . . . . .
H15 H 0.8612 0.5809 0.4696 0.039 Uiso 1 1 calc R . . . .
C16 C 0.8645(4) 0.2805(5) 0.5810(2) 0.0336(8) Uani 1 1 d . . . . .
C17 C 0.7900(4) 0.3898(5) 0.7126(2) 0.0352(8) Uani 1 1 d . . . . .
C18 C 0.9050(4) 0.2767(6) 0.7424(3) 0.0410(8) Uani 1 1 d . . . . .
C19 C 0.9665(5) 0.2445(7) 0.8371(3) 0.0531(11) Uani 1 1 d . . . . .
H19 H 1.0460 0.1724 0.8561 0.064 Uiso 1 1 calc R . . . .
C20 C 0.9058(5) 0.3234(7) 0.9032(3) 0.0560(11) Uani 1 1 d . . . . .
H20 H 0.9440 0.3033 0.9676 0.067 Uiso 1 1 calc R . . . .
C21 C 0.7892(5) 0.4314(6) 0.8733(3) 0.0508(10) Uani 1 1 d . . . . .
C22 C 0.7281(4) 0.4657(5) 0.7786(3) 0.0424(9) Uani 1 1 d . . . . .
H22 H 0.6482 0.5373 0.7598 0.051 Uiso 1 1 calc R . . . .
O0A O 0.9210(4) 0.3544(5) 0.3275(2) 0.0670(10) Uani 1 1 d . . . . .
H0A H 0.8888 0.3065 0.3678 0.100 Uiso 0.6 1 calc R . P A 1
H0AA H 0.9105 0.3302 0.3800 0.100 Uiso 0.4 1 calc R . P B 2
C1 C 0.8412(8) 0.3029(13) 0.2364(6) 0.0438(18) Uani 0.6 1 d . . P C 1
H1A H 0.7891 0.4081 0.2067 0.053 Uiso 0.6 1 calc R . P C 1
C1A C 0.8658(13) 0.211(2) 0.2622(9) 0.052(3) Uani 0.4 1 d . . P C 2
H1AA H 0.9167 0.1061 0.2930 0.063 Uiso 0.4 1 calc R . P C 2
C2 C 0.9368(6) 0.2523(8) 0.1786(3) 0.0644(13) Uani 1 1 d . . . . .
H2AA H 1.0095 0.3406 0.1847 0.097 Uiso 0.6 1 calc GR . P C 1
H2AB H 0.8844 0.2435 0.1133 0.097 Uiso 0.6 1 calc GR . P C 1
H2AC H 0.9793 0.1396 0.1997 0.097 Uiso 0.6 1 calc GR . P C 1
H2BD H 0.8903 0.3521 0.1427 0.097 Uiso 0.4 1 calc GR . P C 2
H2BE H 0.9280 0.1505 0.1379 0.097 Uiso 0.4 1 calc GR . P C 2
H2BF H 1.0352 0.2793 0.2045 0.097 Uiso 0.4 1 calc GR . P C 2
C3 C 0.7320(8) 0.1633(10) 0.2419(5) 0.090(2) Uani 1 1 d . . . . .
H3AA H 0.7784 0.0515 0.2597 0.135 Uiso 0.6 1 calc GR . P C 1
H3AB H 0.6653 0.1520 0.1810 0.135 Uiso 0.6 1 calc GR . P C 1
H3AC H 0.6832 0.1980 0.2883 0.135 Uiso 0.6 1 calc GR . P C 1
H3BD H 0.7039 0.1457 0.2996 0.135 Uiso 0.4 1 calc GR . P C 2
H3BE H 0.7198 0.0547 0.2062 0.135 Uiso 0.4 1 calc GR . P C 2
H3BF H 0.6746 0.2547 0.2049 0.135 Uiso 0.4 1 calc GR . P C 2
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_
_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
C7 N1 H1 126.2 . . ?
C7 N1 C11 107.7(3) . . ?
C11 N1 H1 126.2 . . ?
C13 N2 H2 122.1 . . ?
C13 N2 C15 115.8(3) . . ?
C15 N2 H2 122.1 . . ?
C16 N3 H3 124.2 . . ?
C16 N3 C18 111.6(3) . . ?
C18 N3 H3 124.2 . . ?
C5 C4 H4 120.1 . . ?
C5 C4 C9 119.9(4) . . ?
C9 C4 H4 120.1 . . ?
C4 C5 Cl1 118.2(3) . . ?
C6 C5 Cl1 118.8(4) . . ?
C6 C5 C4 123.0(3) . . ?
C5 C6 H6 121.6 . . ?
C5 C6 C7 116.8(4) . . ?
C7 C6 H6 121.6 . . ?
N1 C7 C6 129.4(4) . . ?
N1 C7 C8 108.6(3) . . ?
C6 C7 C8 121.9(3) . . ?
C7 C8 C10 105.9(3) . . ?
C9 C8 C7 118.7(3) . . ?
C9 C8 C10 135.4(3) . . ?
C4 C9 C8 119.7(4) . . ?
C4 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C8 C10 C15 130.0(3) . . ?
C11 C10 C8 107.3(3) . . ?
C11 C10 C15 122.6(3) . . ?
N1 C11 C12 123.8(3) . . ?
C10 C11 N1 110.5(3) . . ?
C10 C11 C12 125.7(3) . . ?
C11 C12 H12A 109.9 . . ?
C11 C12 H12B 109.9 . . ?
C11 C12 C13 109.0(3) . . ?
H12A C12 H12B 108.3 . . ?
C13 C12 H12A 109.9 . . ?
C13 C12 H12B 109.9 . . ?
N2 C13 C12 108.6(3) . . ?
N2 C13 C16 114.6(3) . . ?
N2 C13 C17 109.8(3) . . ?
C12 C13 C16 109.8(3) . . ?
C17 C13 C12 113.2(3) . . ?
C17 C13 C16 100.8(3) . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C15 C14 H14C 109.5 . . ?
N2 C15 C10 106.9(3) . . ?
N2 C15 C14 108.1(3) . . ?
N2 C15 H15 108.9 . . ?
C10 C15 C14 115.0(3) . . ?
C10 C15 H15 108.9 . . ?
C14 C15 H15 108.9 . . ?
O25 C16 N3 125.4(3) . . ?
O25 C16 C13 126.4(3) . . ?
N3 C16 C13 108.2(3) . . ?
C18 C17 C13 109.5(3) . . ?
C22 C17 C13 130.5(3) . . ?
C22 C17 C18 119.9(3) . . ?
C17 C18 N3 109.7(3) . . ?
C19 C18 N3 128.2(4) . . ?
C19 C18 C17 122.0(4) . . ?
C18 C19 H19 121.1 . . ?
C18 C19 C20 117.8(4) . . ?
C20 C19 H19 121.1 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.0(3) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 Cl2 118.9(3) . . ?
C20 C21 C22 122.5(4) . . ?
C22 C21 Cl2 118.6(3) . . ?
C17 C22 H22 121.2 . . ?
C21 C22 C17 117.7(4) . . ?
C21 C22 H22 121.2 . . ?
C1 O0A H0A 109.5 . . ?
C1A O0A H0AA 109.5 . . ?
O0A C1 H1A 107.0 . . ?
O0A C1 C2 109.5(6) . . ?
O0A C1 C3 111.6(6) . . ?
C2 C1 H1A 107.0 . . ?
C2 C1 C3 114.4(7) . . ?
C3 C1 H1A 107.0 . . ?
O0A C1A H1AA 103.9 . . ?
O0A C1A C2 101.4(10) . . ?
C2 C1A H1AA 103.9 . . ?
C3 C1A O0A 122.2(10) . . ?
C3 C1A H1AA 103.9 . . ?
C3 C1A C2 119.3(9) . . ?
C1 C2 H2AA 109.5 . . ?
C1 C2 H2AB 109.5 . . ?
C1 C2 H2AC 109.5 . . ?
C1A C2 H2BD 109.5 . . ?
C1A C2 H2BE 109.5 . . ?
C1A C2 H2BF 109.5 . . ?
H2AA C2 H2AB 109.5 . . ?
H2AA C2 H2AC 109.5 . . ?
H2AB C2 H2AC 109.5 . . ?
H2BD C2 H2BE 109.5 . . ?
H2BD C2 H2BF 109.5 . . ?
H2BE C2 H2BF 109.5 . . ?
C1 C3 H3AA 109.5 . . ?
C1 C3 H3AB 109.5 . . ?
C1 C3 H3AC 109.5 . . ?
C1A C3 H3BD 109.5 . . ?
C1A C3 H3BE 109.5 . . ?
C1A C3 H3BF 109.5 . . ?
H3AA C3 H3AB 109.5 . . ?
H3AA C3 H3AC 109.5 . . ?
H3AB C3 H3AC 109.5 . . ?
H3BD C3 H3BE 109.5 . . ?
H3BD C3 H3BF 109.5 . . ?
H3BE C3 H3BF 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 C5 1.745(4) . ?
Cl2 C21 1.747(4) . ?
O25 C16 1.214(4) . ?
N1 H1 0.8600 . ?
N1 C7 1.382(5) . ?
N1 C11 1.390(4) . ?
N2 H2 0.8600 . ?
N2 C13 1.472(5) . ?
N2 C15 1.489(5) . ?
N3 H3 0.8600 . ?
N3 C16 1.361(5) . ?
N3 C18 1.401(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(7) . ?
C4 C9 1.386(6) . ?
C5 C6 1.371(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.395(5) . ?
C7 C8 1.418(5) . ?
C8 C9 1.388(5) . ?
C8 C10 1.445(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.357(5) . ?
C10 C15 1.504(5) . ?
C11 C12 1.494(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.534(5) . ?
C13 C16 1.560(5) . ?
C13 C17 1.513(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 C15 1.512(5) . ?
C15 H15 0.9800 . ?
C17 C18 1.387(5) . ?
C17 C22 1.386(5) . ?
C18 C19 1.378(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.389(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.377(7) . ?
C21 C22 1.380(6) . ?
C22 H22 0.9300 . ?
O0A H0A 0.8200 . ?
O0A H0AA 0.8200 . ?
O0A C1 1.410(8) . ?
O0A C1A 1.448(14) . ?
C1 H1A 0.9800 . ?
C1 C2 1.462(10) . ?
C1 C3 1.514(11) . ?
C1A H1AA 0.9800 . ?
C1A C2 1.582(14) . ?
C1A C3 1.314(14) . ?
C2 H2AA 0.9600 . ?
C2 H2AB 0.9600 . ?
C2 H2AC 0.9600 . ?
C2 H2BD 0.9600 . ?
C2 H2BE 0.9600 . ?
C2 H2BF 0.9600 . ?
C3 H3AA 0.9600 . ?
C3 H3AB 0.9600 . ?
C3 H3AC 0.9600 . ?
C3 H3BD 0.9600 . ?
C3 H3BE 0.9600 . ?
C3 H3BF 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 C5 C6 C7 177.7(3) . . . . ?
Cl2 C21 C22 C17 -179.3(3) . . . . ?
N1 C7 C8 C9 177.4(3) . . . . ?
N1 C7 C8 C10 -0.8(4) . . . . ?
N1 C11 C12 C13 164.8(3) . . . . ?
N2 C13 C16 O25 -66.8(4) . . . . ?
N2 C13 C16 N3 113.2(3) . . . . ?
N2 C13 C17 C18 -116.6(3) . . . . ?
N2 C13 C17 C22 61.1(5) . . . . ?
N3 C18 C19 C20 179.4(4) . . . . ?
C4 C5 C6 C7 -1.6(7) . . . . ?
C5 C4 C9 C8 0.6(6) . . . . ?
C5 C6 C7 N1 -175.4(4) . . . . ?
C5 C6 C7 C8 1.1(6) . . . . ?
C6 C7 C8 C9 0.2(6) . . . . ?
C6 C7 C8 C10 -178.0(4) . . . . ?
C7 N1 C11 C10 0.3(4) . . . . ?
C7 N1 C11 C12 -178.4(3) . . . . ?
C7 C8 C9 C4 -1.0(6) . . . . ?
C7 C8 C10 C11 1.0(4) . . . . ?
C7 C8 C10 C15 179.9(4) . . . . ?
C8 C10 C11 N1 -0.8(4) . . . . ?
C8 C10 C11 C12 177.8(3) . . . . ?
C8 C10 C15 N2 166.3(3) . . . . ?
C8 C10 C15 C14 46.3(5) . . . . ?
C9 C4 C5 Cl1 -178.5(3) . . . . ?
C9 C4 C5 C6 0.7(7) . . . . ?
C9 C8 C10 C11 -176.7(4) . . . . ?
C9 C8 C10 C15 2.2(7) . . . . ?
C10 C8 C9 C4 176.5(4) . . . . ?
C10 C11 C12 C13 -13.6(5) . . . . ?
C11 N1 C7 C6 177.3(4) . . . . ?
C11 N1 C7 C8 0.4(4) . . . . ?
C11 C10 C15 N2 -15.0(5) . . . . ?
C11 C10 C15 C14 -134.9(4) . . . . ?
C11 C12 C13 N2 44.0(4) . . . . ?
C11 C12 C13 C16 -82.0(4) . . . . ?
C11 C12 C13 C17 166.3(3) . . . . ?
C12 C13 C16 O25 55.7(5) . . . . ?
C12 C13 C16 N3 -124.3(3) . . . . ?
C12 C13 C17 C18 121.8(3) . . . . ?
C12 C13 C17 C22 -60.5(5) . . . . ?
C13 N2 C15 C10 50.1(4) . . . . ?
C13 N2 C15 C14 174.4(3) . . . . ?
C13 C17 C18 N3 -3.2(4) . . . . ?
C13 C17 C18 C19 174.1(4) . . . . ?
C13 C17 C22 C21 -174.5(4) . . . . ?
C15 N2 C13 C12 -67.7(3) . . . . ?
C15 N2 C13 C16 55.4(4) . . . . ?
C15 N2 C13 C17 168.0(3) . . . . ?
C15 C10 C11 N1 -179.8(3) . . . . ?
C15 C10 C11 C12 -1.2(6) . . . . ?
C16 N3 C18 C17 -0.1(5) . . . . ?
C16 N3 C18 C19 -177.1(4) . . . . ?
C16 C13 C17 C18 4.6(4) . . . . ?
C16 C13 C17 C22 -177.6(4) . . . . ?
C17 C13 C16 O25 175.4(4) . . . . ?
C17 C13 C16 N3 -4.6(4) . . . . ?
C17 C18 C19 C20 2.7(7) . . . . ?
C18 N3 C16 O25 -176.9(4) . . . . ?
C18 N3 C16 C13 3.1(4) . . . . ?
C18 C17 C22 C21 3.1(6) . . . . ?
C18 C19 C20 C21 -0.8(7) . . . . ?
C19 C20 C21 Cl2 178.2(4) . . . . ?
C19 C20 C21 C22 0.1(7) . . . . ?
C20 C21 C22 C17 -1.2(7) . . . . ?
C22 C17 C18 N3 178.8(4) . . . . ?
C22 C17 C18 C19 -4.0(6) . . . . ?
O0A C1 C2 C1A 73.2(12) . . . . ?
O0A C1 C3 C1A -59.0(12) . . . . ?
O0A C1A C2 C1 -63.6(13) . . . . ?
O0A C1A C3 C1 66.5(16) . . . . ?
C1 O0A C1A C2 60.3(12) . . . . ?
C1 O0A C1A C3 -75.4(16) . . . . ?
C1A O0A C1 C2 -77.9(13) . . . . ?
C1A O0A C1 C3 49.8(12) . . . . ?
C2 C1 C3 C1A 66.1(13) . . . . ?
C2 C1A C3 C1 -61.9(14) . . . . ?
C3 C1 C2 C1A -53.0(11) . . . . ?
C3 C1A C2 C1 73.8(15) . . . . ?
