#------------------------------------------------------------------------------
#$Date: 2020-03-05 11:42:52 +0200 (Thu, 05 Mar 2020) $
#$Revision: 249077 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/74/1557482.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1557482
loop_
_publ_author_name
'Ranjan, Subham'
'Devarapalli, Ramesh'
'Kundu, Sudeshna'
'Saha, Subhankar'
'Deolka, Shubham'
'Vangala, Venu R.'
'Reddy, C. Malla'
_publ_section_title
;
 Isomorphism: `molecular similarity to crystal structure similarity' in
 multicomponent forms of analgesic drugs tolfenamic and mefenamic acid
;
_journal_issue                   2
_journal_name_full               IUCrJ
_journal_page_first              173
_journal_page_last               183
_journal_paper_doi               10.1107/S205225251901604X
_journal_volume                  7
_journal_year                    2020
_chemical_formula_moiety         'C14 H11 Cl N O2, C7 H11 N2, H2 O'
_chemical_formula_sum            'C21 H24 Cl N3 O3'
_chemical_formula_weight         401.88
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-09
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_cell_angle_alpha                101.784(6)
_cell_angle_beta                 98.374(6)
_cell_angle_gamma                90.687(6)
_cell_formula_units_Z            2
_cell_length_a                   7.7631(6)
_cell_length_b                   8.0250(6)
_cell_length_c                   16.2297(12)
_cell_measurement_reflns_used    2768
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      65.9260
_cell_measurement_theta_min      5.6170
_cell_volume                     978.32(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    103.00 178.00   1.00    2.00    --  108.00 104.00  30.00   75
  2  ω    130.00 165.00   1.00    2.00    --  108.00 104.00  60.00   35
  3  ω    122.00 148.00   1.00    2.00    --   67.04 111.00  60.00   26
  4  ω    110.00 178.00   1.00    2.00    --  108.00 138.00  90.00   68
  5  ω    146.00 177.00   1.00    2.00    --  108.00  77.00 150.00   31
  6  ω    131.00 178.00   1.00    2.00    --  108.00 138.00 150.00   47
  7  ω    118.00 171.00   1.00    2.00    --  108.00 104.00 120.00   53
  8  ω    100.00 149.00   1.00    2.00    --   67.04 111.00 -30.00   49
  9  ω    108.00 134.00   1.00    2.00    --   67.04  61.00 -90.00   26
 10  ω    104.00 130.00   1.00    2.00    --   67.04 111.00 -90.00   26
 11  ω    109.00 139.00   1.00    2.00    --   67.04 111.00-120.00   30
 12  ω    112.00 143.00   1.00    2.00    --   67.04 118.00-166.00   31
 13  ω    139.00 167.00   1.00    2.00    --  108.00  65.00-180.00   28
 14  ω    130.00 177.00   1.00    2.00    --  108.00  21.00-150.00   47
 15  ω     87.00 142.00   1.00    2.00    --  108.00 138.00-120.00   55
 16  ω     74.00 127.00   1.00    2.00    --  108.00  65.00-180.00   53
 17  ω     82.00 108.00   1.00    2.00    --  108.00  21.00-180.00   26
 18  ω     82.00 107.00   1.00    2.00    --  108.00 -65.00 -60.00   25
 19  ω     85.00 110.00   1.00    2.00    --  108.00-104.00-120.00   25
 20  ω     69.00 109.00   1.00    2.00    --  108.00-104.00 -60.00   40
 21  ω     53.00 102.00   1.00    2.00    --   67.04-111.00 -90.00   49
 22  ω     49.00  74.00   1.00    2.00    --  108.00-104.00 -30.00   25
 23  ω     57.00 100.00   1.00    2.00    --  108.00-104.00  60.00   43
 24  ω     87.00 112.00   1.00    2.00    --  108.00-104.00  90.00   25
 25  ω     85.00 144.00   1.00    2.00    --  108.00 -65.00  90.00   59
 26  ω    148.00 174.00   1.00    2.00    --  108.00 -21.00 150.00   26
 27  ω     90.00 123.00   1.00    2.00    --  108.00 -21.00 150.00   33
 28  ω     93.00 170.00   1.00    2.00    --  108.00  43.00 150.00   77
 29  ω     84.00 175.00   1.00    2.00    --  108.00  54.00  90.00   91
 30  ω     83.00 151.00   1.00    2.00    --  108.00 -89.00 120.00   68
 31  ω     52.00 114.00   1.00    2.00    --  108.00 -77.00  60.00   62
 32  ω     52.00  77.00   1.00    2.00    --  108.00 -21.00 150.00   25
 33  ω     30.00  56.00   1.00    2.00    --  108.00 -65.00  90.00   26
 34  ω     27.00  71.00   1.00    2.00    --  108.00-104.00  90.00   44
 35  ω     -8.00  17.00   1.00    2.00    --   67.04 -61.00 -60.00   25
 36  ω     22.00  84.00   1.00    2.00    --   67.04 -61.00 -60.00   62
 37  ω     29.00  68.00   1.00    2.00    --  108.00-104.00-120.00   39
 38  ω    -29.00  81.00   1.00    1.00    --   26.08 -38.00-180.00  110
 39  ω     65.00 115.00   1.00    2.00    --  108.00  77.00 150.00   50
 40  ω     60.00  85.00   1.00    2.00    --  108.00  43.00 150.00   25
 41  ω     -4.00  87.00   1.00    1.00    --   26.08  57.00 150.00   91
 42  ω     -5.00  94.00   1.00    1.00    --   26.08  57.00  30.00   99
 43  ω     32.00  78.00   1.00    2.00    --   67.04  61.00 -90.00   46
 44  ω     57.00 145.00   1.00    2.00    --   67.04 178.00 -90.00   88
 45  ω    -17.00 151.00   1.00    2.00    --   67.04  15.00  90.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0717363000
_diffrn_orient_matrix_UB_12      0.0652949000
_diffrn_orient_matrix_UB_13      0.0838550000
_diffrn_orient_matrix_UB_21      -0.1870542000
_diffrn_orient_matrix_UB_22      -0.0211658000
_diffrn_orient_matrix_UB_23      -0.0490465000
_diffrn_orient_matrix_UB_31      -0.0131770000
_diffrn_orient_matrix_UB_32      -0.1838922000
_diffrn_orient_matrix_UB_33      0.0136187000
_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  0.0456
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6172
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        66.157
_diffrn_reflns_theta_max         66.157
_diffrn_reflns_theta_min         2.814
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.957
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3366
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0495
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1551
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2829
_reflns_number_total             3366
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ed5019.cif
_cod_data_source_block           tfa-dmap-H2O_1-1-1
_cod_database_code               1557482
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O Cl'
_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   0.591
_shelx_estimated_absorpt_t_min   0.363
_reflns_odcompleteness_completeness 96.26
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 N1-H1 = N3-H3A
 0.87 with sigma of 0.02
3.a Fixed occupancy and ADP/Uiso:
 H1, H3A
3.b Free rotating group:
 O3(H3B,H3C)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C16(H16),
 C17(H17), C18(H18), C19(H19)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_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 2.481
_oxdiff_exptl_absorpt_empirical_full_min 0.430
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 0.71478(8) 1.19551(8) 0.09186(4) 0.0382(2) Uani 1 1 d . . . . .
O1 O 0.55610(19) 0.50022(19) 0.34168(9) 0.0184(3) Uani 1 1 d . . . . .
O2 O 0.2900(2) 0.3879(2) 0.33746(9) 0.0235(4) Uani 1 1 d . . . . .
N1 N 0.5891(2) 0.6832(2) 0.22370(11) 0.0189(4) Uani 1 1 d D . . . .
H1 H 0.632(3) 0.644(3) 0.2675(13) 0.023 Uiso 1 1 d D U . . .
C1 C 0.4003(3) 0.4534(3) 0.30404(13) 0.0165(4) Uani 1 1 d . . . . .
C2 C 0.3510(3) 0.4762(3) 0.21393(12) 0.0158(4) Uani 1 1 d . . . . .
C3 C 0.2057(3) 0.3808(3) 0.16440(13) 0.0191(5) Uani 1 1 d . . . . .
H3 H 0.138223 0.312301 0.190192 0.023 Uiso 1 1 calc R U . . .
C4 C 0.1577(3) 0.3833(3) 0.07941(13) 0.0202(5) Uani 1 1 d . . . . .
H4 H 0.059467 0.316841 0.046904 0.024 Uiso 1 1 calc R U . . .
C5 C 0.2558(3) 0.4848(3) 0.04242(13) 0.0196(5) Uani 1 1 d . . . . .
H5 H 0.224741 0.486961 -0.016158 0.024 Uiso 1 1 calc R U . . .
C6 C 0.3985(3) 0.5832(3) 0.08960(13) 0.0187(5) Uani 1 1 d . . . . .
H6 H 0.463255 0.652319 0.062928 0.022 Uiso 1 1 calc R U . . .
C7 C 0.4488(3) 0.5822(3) 0.17584(12) 0.0164(4) Uani 1 1 d . . . . .
C8 C 0.7048(3) 0.7760(3) 0.18860(12) 0.0174(4) Uani 1 1 d . . . . .
C9 C 0.6521(3) 0.9261(3) 0.16129(13) 0.0192(5) Uani 1 1 d . . . . .
C10 C 0.7739(3) 1.0089(3) 0.12682(13) 0.0221(5) Uani 1 1 d . . . . .
C11 C 0.9410(3) 0.9541(3) 0.12046(13) 0.0235(5) Uani 1 1 d . . . . .
H11 H 1.019648 1.014610 0.096356 0.028 Uiso 1 1 calc R U . . .
C12 C 0.9908(3) 0.8089(3) 0.15005(13) 0.0239(5) Uani 1 1 d . . . . .
H12 H 1.105763 0.770816 0.147895 0.029 Uiso 1 1 calc R U . . .
C13 C 0.8730(3) 0.7196(3) 0.18268(13) 0.0211(5) Uani 1 1 d . . . . .
H13 H 0.906808 0.618410 0.201333 0.025 Uiso 1 1 calc R U . . .
C14 C 0.4742(3) 0.9944(3) 0.17044(15) 0.0260(5) Uani 1 1 d . . . . .
H14A H 0.399969 0.969990 0.114762 0.039 Uiso 1 1 calc R U . . .
H14B H 0.485313 1.117807 0.192393 0.039 Uiso 1 1 calc R U . . .
H14C H 0.421737 0.939728 0.210121 0.039 Uiso 1 1 calc R U . . .
N2 N 1.0721(2) -0.1642(2) 0.39099(11) 0.0182(4) Uani 1 1 d . . . . .
N3 N 0.7483(2) 0.2296(2) 0.36356(11) 0.0206(4) Uani 1 1 d D . . . .
H3A H 0.686(3) 0.315(3) 0.3581(16) 0.025 Uiso 1 1 d D U . . .
C15 C 0.9658(3) -0.0372(3) 0.38155(12) 0.0168(5) Uani 1 1 d . . . . .
C16 C 0.7972(3) -0.0329(3) 0.40652(12) 0.0181(5) Uani 1 1 d . . . . .
H16 H 0.755859 -0.123390 0.429126 0.022 Uiso 1 1 calc R U . . .
C17 C 0.6955(3) 0.1016(3) 0.39784(13) 0.0210(5) Uani 1 1 d . . . . .
H17 H 0.584757 0.105302 0.416360 0.025 Uiso 1 1 calc R U . . .
C18 C 0.9055(3) 0.2286(3) 0.33753(13) 0.0203(5) Uani 1 1 d . . . . .
H18 H 0.939643 0.319054 0.312840 0.024 Uiso 1 1 calc R U . . .
C19 C 1.0162(3) 0.1009(3) 0.34587(12) 0.0194(5) Uani 1 1 d . . . . .
H19 H 1.127176 0.103771 0.327922 0.023 Uiso 1 1 calc R U . . .
C20 C 1.0111(3) -0.3132(3) 0.41870(14) 0.0230(5) Uani 1 1 d . . . . .
H20A H 0.990128 -0.279973 0.477822 0.034 Uiso 1 1 calc R U . . .
H20B H 1.099653 -0.399269 0.414717 0.034 Uiso 1 1 calc R U . . .
H20C H 0.902533 -0.360411 0.382186 0.034 Uiso 1 1 calc R U . . .
C21 C 1.2516(3) -0.1569(3) 0.37506(14) 0.0236(5) Uani 1 1 d . . . . .
H21A H 1.253702 -0.184044 0.313554 0.035 Uiso 1 1 calc R U . . .
H21B H 1.318579 -0.239604 0.401828 0.035 Uiso 1 1 calc R U . . .
H21C H 1.303167 -0.042064 0.399092 0.035 Uiso 1 1 calc R U . . .
O3 O 0.3861(2) 0.2898(2) 0.49152(9) 0.0242(4) Uani 1 1 d G . . . .
H3B H 0.369199 0.343147 0.449617 0.036 Uiso 1 1 d G U . . .
H3C H 0.402851 0.370491 0.537047 0.036 Uiso 1 1 d G 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_
_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 111.7(18) . . ?
C7 N1 C8 123.71(17) . . ?
C8 N1 H1 117.0(18) . . ?
O1 C1 C2 117.89(18) . . ?
O2 C1 O1 123.62(18) . . ?
O2 C1 C2 118.47(18) . . ?
C3 C2 C1 117.71(19) . . ?
C3 C2 C7 118.85(18) . . ?
C7 C2 C1 123.37(18) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 122.1(2) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.63(19) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.03(19) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
N1 C7 C2 120.42(18) . . ?
N1 C7 C6 121.2(2) . . ?
C6 C7 C2 118.35(19) . . ?
C9 C8 N1 120.26(19) . . ?
C13 C8 N1 119.3(2) . . ?
C13 C8 C9 120.4(2) . . ?
C8 C9 C14 121.6(2) . . ?
C10 C9 C8 116.5(2) . . ?
C10 C9 C14 121.9(2) . . ?
C9 C10 Cl1 118.28(17) . . ?
C11 C10 Cl1 118.06(18) . . ?
C11 C10 C9 123.6(2) . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.6(2) . . ?
C12 C11 H11 120.7 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.9(2) . . ?
C13 C12 H12 120.0 . . ?
C8 C13 H13 119.5 . . ?
C12 C13 C8 120.9(2) . . ?
C12 C13 H13 119.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C15 N2 C20 120.55(18) . . ?
C15 N2 C21 121.24(19) . . ?
C21 N2 C20 118.20(18) . . ?
C17 N3 H3A 122.7(18) . . ?
C18 N3 H3A 116.7(18) . . ?
C18 N3 C17 120.54(19) . . ?
N2 C15 C16 121.8(2) . . ?
N2 C15 C19 121.48(19) . . ?
C16 C15 C19 116.7(2) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.7(2) . . ?
C17 C16 H16 120.1 . . ?
N3 C17 C16 121.6(2) . . ?
N3 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
N3 C18 H18 119.3 . . ?
N3 C18 C19 121.4(2) . . ?
C19 C18 H18 119.3 . . ?
C15 C19 H19 120.0 . . ?
C18 C19 C15 120.0(2) . . ?
C18 C19 H19 120.0 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H3B O3 H3C 104.5 . . ?
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 C10 1.750(2) . ?
O1 C1 1.288(3) . ?
O2 C1 1.242(3) . ?
N1 H1 0.860(16) . ?
N1 C7 1.386(3) . ?
N1 C8 1.412(3) . ?
C1 C2 1.506(3) . ?
C2 C3 1.403(3) . ?
C2 C7 1.421(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.399(3) . ?
C8 C9 1.411(3) . ?
C8 C13 1.397(3) . ?
C9 C10 1.393(3) . ?
C9 C14 1.508(3) . ?
C10 C11 1.386(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(3) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N2 C15 1.338(3) . ?
N2 C20 1.457(3) . ?
N2 C21 1.456(3) . ?
N3 H3A 0.857(17) . ?
N3 C17 1.350(3) . ?
N3 C18 1.348(3) . ?
C15 C16 1.424(3) . ?
C15 C19 1.426(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.363(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.361(3) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O3 H3B 0.8702 . ?
O3 H3C 0.8699 . ?
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 C10 C11 C12 178.31(15) . . . . ?
O1 C1 C2 C3 160.81(18) . . . . ?
O1 C1 C2 C7 -16.0(3) . . . . ?
O2 C1 C2 C3 -17.9(3) . . . . ?
O2 C1 C2 C7 165.26(19) . . . . ?
N1 C8 C9 C10 -179.49(17) . . . . ?
N1 C8 C9 C14 1.5(3) . . . . ?
N1 C8 C13 C12 -178.86(17) . . . . ?
C1 C2 C3 C4 -175.19(19) . . . . ?
C1 C2 C7 N1 -5.7(3) . . . . ?
C1 C2 C7 C6 175.00(18) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C2 C7 N1 177.53(18) . . . . ?
C3 C2 C7 C6 -1.8(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C5 C6 C7 N1 -178.59(19) . . . . ?
C5 C6 C7 C2 0.7(3) . . . . ?
C7 N1 C8 C9 74.5(3) . . . . ?
C7 N1 C8 C13 -106.7(2) . . . . ?
C7 C2 C3 C4 1.8(3) . . . . ?
C8 N1 C7 C2 172.20(19) . . . . ?
C8 N1 C7 C6 -8.5(3) . . . . ?
C8 C9 C10 Cl1 179.93(15) . . . . ?
C8 C9 C10 C11 -1.6(3) . . . . ?
C9 C8 C13 C12 0.0(3) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 C13 1.9(3) . . . . ?
C11 C12 C13 C8 -1.8(3) . . . . ?
C13 C8 C9 C10 1.7(3) . . . . ?
C13 C8 C9 C14 -177.27(18) . . . . ?
C14 C9 C10 Cl1 -1.1(3) . . . . ?
C14 C9 C10 C11 177.3(2) . . . . ?
N2 C15 C16 C17 178.19(18) . . . . ?
N2 C15 C19 C18 -179.67(18) . . . . ?
N3 C18 C19 C15 1.0(3) . . . . ?
C15 C16 C17 N3 2.0(3) . . . . ?
C16 C15 C19 C18 0.3(3) . . . . ?
C17 N3 C18 C19 -0.9(3) . . . . ?
C18 N3 C17 C16 -0.7(3) . . . . ?
C19 C15 C16 C17 -1.8(3) . . . . ?
C20 N2 C15 C16 6.8(3) . . . . ?
C20 N2 C15 C19 -173.16(17) . . . . ?
C21 N2 C15 C16 -172.37(17) . . . . ?
C21 N2 C15 C19 7.6(3) . . . . ?
