#------------------------------------------------------------------------------
#$Date: 2020-03-05 11:42:52 +0200 (Thu, 05 Mar 2020) $
#$Revision: 249077 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/74/1557483.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_1557483
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 H12 Cl N O2, C14 H11 Cl N O2, C7 H11 N2'
_chemical_formula_sum            'C35 H34 Cl2 N4 O4'
_chemical_formula_weight         645.56
_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             2019-10-10
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_cell_angle_alpha                106.966(6)
_cell_angle_beta                 105.782(6)
_cell_angle_gamma                103.324(5)
_cell_formula_units_Z            2
_cell_length_a                   10.8864(7)
_cell_length_b                   12.2705(7)
_cell_length_c                   13.7811(10)
_cell_measurement_reflns_used    2351
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3500
_cell_measurement_theta_min      3.9140
_cell_volume                     1595.5(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -87.00  -61.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.5717  178.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega   39.00  111.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       30.9779  178.0000  -60.0000 72

#__ type_ start__ end____ width___ exp.time_
  3 omega  -20.00   85.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       30.9779  -99.0000    0.0000 105

#__ type_ start__ end____ width___ exp.time_
  4 omega  -20.00   49.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       30.9779  -99.0000  -60.0000 69

#__ type_ start__ end____ width___ exp.time_
  5 omega  -55.00  127.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       30.9779  -19.0000    0.0000 182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0370971000
_diffrn_orient_matrix_UB_12      0.0009268000
_diffrn_orient_matrix_UB_13      -0.0350149000
_diffrn_orient_matrix_UB_21      0.0121346000
_diffrn_orient_matrix_UB_22      0.0629540000
_diffrn_orient_matrix_UB_23      0.0141477000
_diffrn_orient_matrix_UB_31      0.0603936000
_diffrn_orient_matrix_UB_32      0.0125219000
_diffrn_orient_matrix_UB_33      0.0437821000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8477
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         3.916
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
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    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     582
_refine_ls_number_reflns         5577
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0755
_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)+(0.0721P)²+1.2105P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1831
_refine_ls_wR_factor_ref         0.2038
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3784
_reflns_number_total             5577
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ed5019.cif
_cod_data_source_block           tfa-dmap_2-1
_cod_original_cell_volume        1595.53(19)
_cod_database_code               1557483
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_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   0.976
_shelx_estimated_absorpt_t_min   0.920
_reflns_odcompleteness_completeness 98.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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) groups
2. Restrained distances
 N5-H5 = N2-H2 = N4-H4A = N6-H6A = N1-H1
 0.87 with sigma of 0.02
 O3-H3
 0.82 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C49) = Uanis(C10)
Uanis(C47) = Uanis(C25)
4. Others
 Sof(Cl3)=Sof(Cl4)=Sof(N5)=Sof(H5)=Sof(C43)=Sof(H43)=Sof(C40)=Sof(C42)=
 Sof(C46)=Sof(C41)=Sof(H41)=Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(H48C)=Sof(C39)=
 Sof(C44)=Sof(H44)=Sof(C36)=Sof(H36)=Sof(C47)=Sof(H47)=Sof(C37)=Sof(H37A)=
 Sof(H37B)=Sof(H37C)=Sof(C49)=Sof(C38)=Sof(H38)=Sof(C45)=1-FVAR(1)
 Sof(Cl2)=Sof(N2)=Sof(H2)=Sof(C22)=Sof(C23)=Sof(C24)=Sof(C25)=Sof(H25)=
 Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=
 Sof(Cl1)=Sof(C8)=Sof(C9)=Sof(C10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=Sof(C13)=
 Sof(H13)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=FVAR(1)
 Sof(N6)=Sof(H6A)=1-FVAR(2)
 Sof(N1)=Sof(H1)=FVAR(2)
5.a Fixed occupancy and ADP/Uiso:
 H3, H2, H1, H4A, H5, H6A
5.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20), C25(H25), C26(H26), C27(H27), C3(H3A),
  C4(H4), C5(H5A), C6(H6), C11(H11), C12(H12), C13(H13), C30(H30), C31(H31),
 C32(H32), C33(H33), C43(H43), C41(H41), C44(H44), C36(H36), C47(H47), C38(H38)
5.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C14(H14A,H14B,H14C), C34(H34A,H34B,H34C), C35(H35A,H35B,
 H35C), C48(H48A,H48B,H48C), C37(H37A,H37B,H37C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
O3 O 0.7045(3) 0.5557(2) 0.3362(2) 0.0732(8) Uani 1 1 d D . . . .
H3 H 0.734(4) 0.527(4) 0.288(3) 0.110 Uiso 1 1 d D U . . .
O4 O 0.9145(2) 0.6754(2) 0.43924(19) 0.0674(8) Uani 1 1 d . . . . .
C15 C 0.7934(3) 0.6449(3) 0.4225(2) 0.0440(7) Uani 1 1 d . . . . .
C16 C 0.7347(3) 0.7074(3) 0.4980(2) 0.0408(7) Uani 1 1 d . . . . .
C17 C 0.5967(3) 0.6647(3) 0.4740(3) 0.0596(10) Uani 1 1 d . . . . .
H17 H 0.543534 0.596317 0.411450 0.071 Uiso 1 1 calc R U . . .
C18 C 0.5349(4) 0.7191(4) 0.5386(3) 0.0704(11) Uani 1 1 d . . . . .
H18 H 0.441618 0.688630 0.520008 0.084 Uiso 1 1 calc R U . . .
C19 C 0.6134(4) 0.8193(3) 0.6312(3) 0.0612(10) Uani 1 1 d . . . . .
H19 H 0.572905 0.856993 0.675923 0.073 Uiso 1 1 calc R U . . .
C20 C 0.7501(3) 0.8643(3) 0.6585(3) 0.0556(9) Uani 1 1 d . . . . .
H20 H 0.801141 0.932604 0.721705 0.067 Uiso 1 1 calc R U . . .
C21 C 0.8157(3) 0.8099(3) 0.5934(2) 0.0461(8) Uani 1 1 d . . . . .
Cl2 Cl 1.2336(2) 1.09870(18) 1.02376(13) 0.0932(7) Uani 0.649(3) 1 d . . P A 1
N2 N 0.9517(15) 0.8672(10) 0.6149(11) 0.050(2) Uani 0.649(3) 1 d D . P A 1
H2 H 0.984(6) 0.830(5) 0.569(4) 0.060 Uiso 0.6493 1 d D U P A 1
C22 C 1.0366(8) 0.9765(10) 0.7025(7) 0.0450(18) Uani 0.649(3) 1 d . . P A 1
C23 C 1.0834(8) 0.9790(7) 0.8070(9) 0.0486(19) Uani 0.649(3) 1 d . . P A 1
C24 C 1.1683(7) 1.0867(7) 0.8890(6) 0.0543(18) Uani 0.649(3) 1 d . . P A 1
C25 C 1.2073(9) 1.1928(8) 0.8708(7) 0.057(2) Uani 0.649(3) 1 d . . P A 1
H25 H 1.264863 1.264789 0.928127 0.069 Uiso 0.649(3) 1 calc R U P A 1
C26 C 1.1597(6) 1.1895(5) 0.7672(5) 0.0628(15) Uani 0.649(3) 1 d . . P A 1
H26 H 1.185026 1.258885 0.752485 0.075 Uiso 0.649(3) 1 calc R U P A 1
C27 C 1.0728(15) 1.0809(14) 0.6842(10) 0.062(3) Uani 0.649(3) 1 d . . P A 1
H27 H 1.038083 1.078874 0.613906 0.074 Uiso 0.649(3) 1 calc R U P A 1
C28 C 1.0462(18) 0.8689(10) 0.8329(15) 0.069(3) Uani 0.649(3) 1 d . . P A 1
H28A H 0.974486 0.869169 0.860902 0.104 Uiso 0.649(3) 1 calc R U P A 1
H28B H 1.123780 0.868851 0.886598 0.104 Uiso 0.649(3) 1 calc R U P A 1
H28C H 1.016298 0.797897 0.768018 0.104 Uiso 0.649(3) 1 calc R U P A 1
O1 O 0.5692(3) 0.3446(2) 0.0652(2) 0.0746(8) Uani 1 1 d . . . . .
O2 O 0.7762(3) 0.4448(2) 0.18603(19) 0.0722(8) Uani 1 1 d . . . . .
C1 C 0.6942(3) 0.3682(3) 0.0957(2) 0.0456(8) Uani 1 1 d . . . . .
C2 C 0.7517(3) 0.3009(3) 0.0204(2) 0.0400(7) Uani 1 1 d . . . . .
C3 C 0.8901(3) 0.3405(3) 0.0459(3) 0.0546(9) Uani 1 1 d . . . . .
H3A H 0.943519 0.406808 0.110092 0.066 Uiso 1 1 calc R U . . .
C4 C 0.9531(4) 0.2873(3) -0.0185(3) 0.0628(10) Uani 1 1 d . . . . .
H4 H 1.046539 0.317765 0.000686 0.075 Uiso 1 1 calc R U . . .
C5 C 0.8744(3) 0.1877(3) -0.1122(3) 0.0562(9) Uani 1 1 d . . . . .
H5A H 0.915225 0.149282 -0.156264 0.067 Uiso 1 1 calc R U . . .
C6 C 0.7378(3) 0.1446(3) -0.1412(3) 0.0562(9) Uani 1 1 d . . . . .
H6 H 0.686560 0.077481 -0.205284 0.067 Uiso 1 1 calc R U . . .
C7 C 0.6718(3) 0.1996(3) -0.0762(3) 0.0498(8) Uani 1 1 d . . . . .
Cl1 Cl 0.2722(3) -0.0683(2) -0.51096(16) 0.1248(10) Uani 0.649(3) 1 d . . P A 1
N1 N 0.5348(11) 0.143(3) -0.099(2) 0.057(5) Uani 0.67(12) 1 d D . P A 1
H1 H 0.502(6) 0.183(5) -0.056(4) 0.068 Uiso 0.6702 1 d D U P A 1
C8 C 0.4504(8) 0.0381(11) -0.1895(7) 0.0464(17) Uani 0.649(3) 1 d . . P A 1
C9 C 0.4091(7) 0.0400(7) -0.2931(10) 0.0509(17) Uani 0.649(3) 1 d . . P A 1
C10 C 0.3240(8) -0.0671(11) -0.3766(8) 0.059(2) Uani 0.649(3) 1 d . . P A 1
C11 C 0.2774(7) -0.1731(7) -0.3673(8) 0.067(2) Uani 0.649(3) 1 d . . P A 1
H11 H 0.220110 -0.242313 -0.427795 0.081 Uiso 0.649(3) 1 calc R U P A 1
C12 C 0.3181(6) -0.1754(5) -0.2639(6) 0.0698(17) Uani 0.649(3) 1 d . . P A 1
H12 H 0.288415 -0.246412 -0.252574 0.084 Uiso 0.649(3) 1 calc R U P A 1
C13 C 0.4030(14) -0.0706(13) -0.1787(10) 0.063(3) Uani 0.649(3) 1 d . . P A 1
H13 H 0.430594 -0.072543 -0.109343 0.076 Uiso 0.649(3) 1 calc R U P A 1
C14 C 0.4575(15) 0.1532(12) -0.3122(14) 0.088(4) Uani 0.649(3) 1 d . . P A 1
H14A H 0.493414 0.221567 -0.244409 0.131 Uiso 0.649(3) 1 calc R U P A 1
H14B H 0.383199 0.161804 -0.362363 0.131 Uiso 0.649(3) 1 calc R U P A 1
H14C H 0.527145 0.149114 -0.342070 0.131 Uiso 0.649(3) 1 calc R U P A 1
N3 N 0.1498(3) 0.5440(3) 0.2998(2) 0.0554(8) Uani 1 1 d . . . . .
N4 N 0.4116(3) 0.4344(3) 0.1599(2) 0.0587(8) Uani 1 1 d D . . . .
H4A H 0.473(3) 0.424(3) 0.130(3) 0.070 Uiso 1 1 d D U . . .
C29 C 0.2361(3) 0.5067(3) 0.2530(2) 0.0424(7) Uani 1 1 d . . . . .
C30 C 0.2875(3) 0.4180(3) 0.2729(3) 0.0552(9) Uani 1 1 d . . . . .
H30 H 0.262195 0.381732 0.318281 0.066 Uiso 1 1 calc R U . . .
C31 C 0.3756(3) 0.3842(3) 0.2253(3) 0.0524(8) Uani 1 1 d . . . . .
H31 H 0.410240 0.325487 0.239257 0.063 Uiso 1 1 calc R U . . .
C32 C 0.3635(4) 0.5178(3) 0.1367(3) 0.0560(9) Uani 1 1 d . . . . .
H32 H 0.390611 0.551484 0.090392 0.067 Uiso 1 1 calc R U . . .
C33 C 0.2739(4) 0.5543(3) 0.1810(3) 0.0582(9) Uani 1 1 d . . . . .
H33 H 0.238411 0.610882 0.162877 0.070 Uiso 1 1 calc R U . . .
C34 C 0.1056(4) 0.4910(3) 0.3696(3) 0.0640(10) Uani 1 1 d . . . . .
H34A H 0.059159 0.405675 0.330065 0.096 Uiso 1 1 calc R U . . .
H34B H 0.045221 0.527767 0.394500 0.096 Uiso 1 1 calc R U . . .
H34C H 0.182746 0.503992 0.431143 0.096 Uiso 1 1 calc R U . . .
C35 C 0.1013(4) 0.6377(3) 0.2806(3) 0.0649(10) Uani 1 1 d . . . . .
H35A H 0.176921 0.707554 0.297332 0.097 Uiso 1 1 calc R U . . .
H35B H 0.050753 0.658695 0.326064 0.097 Uiso 1 1 calc R U . . .
H35C H 0.043879 0.609566 0.205476 0.097 Uiso 1 1 calc R U . . .
Cl3 Cl 1.2458(4) 1.2882(3) 0.8528(3) 0.0871(12) Uani 0.351(3) 1 d . . P A 2
Cl4 Cl 0.2443(4) -0.2714(3) -0.3480(3) 0.1012(14) Uani 0.351(3) 1 d . . P A 2
N5 N 0.954(3) 0.8354(19) 0.6365(19) 0.049(4) Uani 0.351(3) 1 d D . P A 2
H5 H 0.988(11) 0.797(9) 0.592(7) 0.059 Uiso 0.3507 1 d D U P A 2
N6 N 0.532(2) 0.179(6) -0.127(5) 0.052(12) Uani 0.33(12) 1 d D . P A 2
H6A H 0.490(11) 0.211(10) -0.086(8) 0.063 Uiso 0.3298 1 d D U P A 2
C43 C 1.1551(15) 1.0061(13) 0.9342(10) 0.089(4) Uani 0.351(3) 1 d . . P A 2
H43 H 1.172949 0.989972 0.997541 0.107 Uiso 0.351(3) 1 calc R U P A 2
C40 C 0.3973(14) -0.034(2) -0.2336(10) 0.049(3) Uani 0.351(3) 1 d . . P A 2
C42 C 1.0916(13) 1.0504(18) 0.7415(9) 0.045(3) Uani 0.351(3) 1 d . . P A 2
C46 C 1.0406(15) 0.9357(14) 0.7357(16) 0.043(3) Uani 0.351(3) 1 d . . P A 2
C41 C 0.3324(16) 0.0183(18) -0.4205(10) 0.099(5) Uani 0.351(3) 1 d . . P A 2
H41 H 0.310808 0.035990 -0.482955 0.119 Uiso 0.351(3) 1 calc R U P A 2
C48 C 1.063(4) 1.076(3) 0.6420(17) 0.076(7) Uani 0.351(3) 1 d . . P A 2
H48A H 0.985047 1.012306 0.585171 0.114 Uiso 0.351(3) 1 calc R U P A 2
H48B H 1.139654 1.082513 0.619801 0.114 Uiso 0.351(3) 1 calc R U P A 2
H48C H 1.044963 1.151407 0.655739 0.114 Uiso 0.351(3) 1 calc R U P A 2
C39 C 1.1789(16) 1.1416(14) 0.8410(14) 0.053(4) Uani 0.351(3) 1 d . . P A 2
C44 C 0.414(3) 0.107(3) -0.3205(19) 0.075(7) Uani 0.351(3) 1 d . . P A 2
H44 H 0.447589 0.186411 -0.314167 0.090 Uiso 0.351(3) 1 calc R U P A 2
C36 C 1.074(3) 0.920(2) 0.8320(19) 0.073(8) Uani 0.351(3) 1 d . . P A 2
H36 H 1.037025 0.841944 0.828643 0.088 Uiso 0.351(3) 1 calc R U P A 2
C47 C 1.2068(14) 1.1176(13) 0.9321(12) 0.057(2) Uani 0.351(3) 1 d . . P A 2
H47 H 1.264522 1.180557 0.997449 0.069 Uiso 0.351(3) 1 calc R U P A 2
C37 C 0.433(3) -0.066(3) -0.1365(17) 0.075(6) Uani 0.351(3) 1 d . . P A 2
H37A H 0.466180 -0.133027 -0.152005 0.112 Uiso 0.351(3) 1 calc R U P A 2
H37B H 0.354531 -0.088417 -0.118328 0.112 Uiso 0.351(3) 1 calc R U P A 2
H37C H 0.502571 0.002079 -0.076238 0.112 Uiso 0.351(3) 1 calc R U P A 2
C49 C 0.3114(15) -0.1272(16) -0.3334(14) 0.059(2) Uani 0.351(3) 1 d . . P A 2
C38 C 0.285(2) -0.094(3) -0.4246(12) 0.074(5) Uani 0.351(3) 1 d . . P A 2
H38 H 0.230488 -0.154689 -0.492300 0.089 Uiso 0.351(3) 1 calc R U P A 2
C45 C 0.4478(15) 0.0779(15) -0.2287(18) 0.047(3) Uani 0.351(3) 1 d . . P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cl Cl 0.1484 0.1585 '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'
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
C15 O3 H3 115(3) . . ?
O3 C15 C16 114.0(3) . . ?
O4 C15 O3 122.7(3) . . ?
O4 C15 C16 123.2(3) . . ?
C17 C16 C15 119.3(3) . . ?
C17 C16 C21 118.8(3) . . ?
C21 C16 C15 121.8(3) . . ?
C16 C17 H17 118.7 . . ?
C18 C17 C16 122.7(3) . . ?
C18 C17 H17 118.7 . . ?
C17 C18 H18 120.7 . . ?
C17 C18 C19 118.6(3) . . ?
C19 C18 H18 120.7 . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.9(3) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 119.3 . . ?
C19 C20 C21 121.5(3) . . ?
C21 C20 H20 119.3 . . ?
C16 C21 C20 117.5(3) . . ?
N2 C21 C16 121.7(6) . . ?
N2 C21 C20 120.1(6) . . ?
N5 C21 C16 120.3(10) . . ?
N5 C21 C20 119.8(11) . . ?
C21 N2 H2 115(5) . . ?
C21 N2 C22 125.4(11) . . ?
C22 N2 H2 120(5) . . ?
C23 C22 N2 120.4(10) . . ?
C27 C22 N2 120.0(9) . . ?
C27 C22 C23 119.6(11) . . ?
C22 C23 C28 122.4(13) . . ?
C24 C23 C22 118.2(7) . . ?
C24 C23 C28 119.4(12) . . ?
C23 C24 Cl2 121.6(7) . . ?
C23 C24 C25 122.5(8) . . ?
C25 C24 Cl2 115.9(5) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 C24 118.8(7) . . ?
C26 C25 H25 120.6 . . ?
C25 C26 H26 120.6 . . ?
C25 C26 C27 118.8(9) . . ?
C27 C26 H26 120.6 . . ?
C22 C27 C26 122.0(11) . . ?
C22 C27 H27 119.0 . . ?
C26 C27 H27 119.0 . . ?
C23 C28 H28A 109.5 . . ?
C23 C28 H28B 109.5 . . ?
C23 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O1 C1 O2 124.1(3) . . ?
O1 C1 C2 118.8(3) . . ?
O2 C1 C2 117.1(3) . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 C7 117.9(3) . . ?
C7 C2 C1 123.4(3) . . ?
C2 C3 H3A 118.2 . . ?
C4 C3 C2 123.5(3) . . ?
C4 C3 H3A 118.2 . . ?
C3 C4 H4 120.9 . . ?
C3 C4 C5 118.2(3) . . ?
C5 C4 H4 120.9 . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5A 119.6 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.4(3) . . ?
C7 C6 H6 119.3 . . ?
C2 C7 C6 118.2(3) . . ?
C2 C7 N6 120.4(10) . . ?
C6 C7 N6 117.9(13) . . ?
N1 C7 C2 121.0(5) . . ?
N1 C7 C6 120.0(5) . . ?
C7 N1 H1 114(5) . . ?
C7 N1 C8 124.7(10) . . ?
C8 N1 H1 121(5) . . ?
C9 C8 N1 121(3) . . ?
C13 C8 N1 121(2) . . ?
C13 C8 C9 117.6(11) . . ?
C8 C9 C14 121.0(11) . . ?
C10 C9 C8 116.8(9) . . ?
C10 C9 C14 122.1(12) . . ?
C9 C10 Cl1 117.9(11) . . ?
C11 C10 Cl1 115.9(6) . . ?
C11 C10 C9 126.2(13) . . ?
C10 C11 H11 121.4 . . ?
C10 C11 C12 117.2(7) . . ?
C12 C11 H11 121.4 . . ?
C11 C12 H12 120.8 . . ?
C13 C12 C11 118.3(8) . . ?
C13 C12 H12 120.8 . . ?
C8 C13 H13 118.1 . . ?
C12 C13 C8 123.9(11) . . ?
C12 C13 H13 118.1 . . ?
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 . . ?
C29 N3 C34 121.0(3) . . ?
C29 N3 C35 120.8(3) . . ?
C35 N3 C34 118.2(3) . . ?
C31 N4 H4A 127(3) . . ?
C31 N4 C32 121.8(3) . . ?
C32 N4 H4A 111(3) . . ?
N3 C29 C30 121.8(3) . . ?
N3 C29 C33 120.9(3) . . ?
C30 C29 C33 117.3(3) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 C29 119.9(3) . . ?
C31 C30 H30 120.0 . . ?
N4 C31 C30 120.7(3) . . ?
N4 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
N4 C32 H32 119.9 . . ?
N4 C32 C33 120.2(3) . . ?
C33 C32 H32 119.9 . . ?
C29 C33 H33 120.0 . . ?
C32 C33 C29 120.1(3) . . ?
C32 C33 H33 120.0 . . ?
N3 C34 H34A 109.5 . . ?
N3 C34 H34B 109.5 . . ?
N3 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N3 C35 H35A 109.5 . . ?
N3 C35 H35B 109.5 . . ?
N3 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C21 N5 H5 115(8) . . ?
C21 N5 C46 122(2) . . ?
C46 N5 H5 121(9) . . ?
C7 N6 H6A 118(9) . . ?
C7 N6 C45 122(2) . . ?
C45 N6 H6A 117(9) . . ?
C36 C43 H43 123.7 . . ?
C47 C43 H43 123.7 . . ?
C47 C43 C36 112.6(16) . . ?
C49 C40 C37 118(2) . . ?
C45 C40 C37 122(2) . . ?
C45 C40 C49 120.3(16) . . ?
C46 C42 C48 120(2) . . ?
C46 C42 C39 119.9(14) . . ?
C39 C42 C48 120(2) . . ?
C42 C46 N5 123.8(18) . . ?
C42 C46 C36 115.9(19) . . ?
C36 C46 N5 120.3(16) . . ?
C44 C41 H41 121.3 . . ?
C38 C41 H41 121.3 . . ?
C38 C41 C44 117.3(17) . . ?
C42 C48 H48A 109.5 . . ?
C42 C48 H48B 109.5 . . ?
C42 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C42 C39 Cl3 121.7(17) . . ?
C47 C39 Cl3 118.1(10) . . ?
C47 C39 C42 120.1(18) . . ?
C41 C44 H44 119.8 . . ?
C41 C44 C45 120(2) . . ?
C45 C44 H44 119.8 . . ?
C43 C36 H36 116.2 . . ?
C46 C36 C43 128(2) . . ?
C46 C36 H36 116.2 . . ?
C43 C47 H47 118.1 . . ?
C39 C47 C43 123.7(13) . . ?
C39 C47 H47 118.1 . . ?
C40 C37 H37A 109.5 . . ?
C40 C37 H37B 109.5 . . ?
C40 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C40 C49 Cl4 123.8(18) . . ?
C40 C49 C38 116(2) . . ?
C38 C49 Cl4 120.3(13) . . ?
C41 C38 C49 124.4(16) . . ?
C41 C38 H38 117.8 . . ?
C49 C38 H38 117.8 . . ?
C40 C45 N6 123(5) . . ?
C40 C45 C44 122(2) . . ?
C44 C45 N6 116(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
O3 H3 0.84(2) . ?
O3 C15 1.294(4) . ?
O4 C15 1.220(4) . ?
C15 C16 1.483(4) . ?
C16 C17 1.381(4) . ?
C16 C21 1.408(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.369(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.370(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.362(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.408(4) . ?
C21 N2 1.390(15) . ?
C21 N5 1.39(3) . ?
Cl2 C24 1.746(7) . ?
N2 H2 0.87(2) . ?
N2 C22 1.410(17) . ?
C22 C23 1.378(12) . ?
C22 C27 1.367(18) . ?
C23 C24 1.370(13) . ?
C23 C28 1.491(12) . ?
C24 C25 1.390(16) . ?
C25 H25 0.9300 . ?
C25 C26 1.365(12) . ?
C26 H26 0.9300 . ?
C26 C27 1.385(16) . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
O1 C1 1.245(4) . ?
O2 C1 1.248(4) . ?
C1 C2 1.496(4) . ?
C2 C3 1.380(4) . ?
C2 C7 1.408(4) . ?
C3 H3A 0.9300 . ?
C3 C4 1.373(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(4) . ?
C5 H5A 0.9300 . ?
C5 C6 1.357(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.412(4) . ?
C7 N1 1.395(18) . ?
C7 N6 1.42(4) . ?
Cl1 C10 1.778(12) . ?
N1 H1 0.86(2) . ?
N1 C8 1.398(16) . ?
C8 C9 1.383(12) . ?
C8 C13 1.382(18) . ?
C9 C10 1.374(13) . ?
C9 C14 1.493(15) . ?
C10 C11 1.34(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(13) . ?
C12 H12 0.9300 . ?
C12 C13 1.366(15) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N3 C29 1.366(4) . ?
N3 C34 1.434(4) . ?
N3 C35 1.431(4) . ?
N4 H4A 0.884(19) . ?
N4 C31 1.323(5) . ?
N4 C32 1.331(5) . ?
C29 C30 1.394(4) . ?
C29 C33 1.395(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.374(5) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C32 C33 1.375(5) . ?
C33 H33 0.9300 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
Cl3 C39 1.719(18) . ?
Cl4 C49 1.68(2) . ?
N5 H5 0.87(2) . ?
N5 C46 1.43(3) . ?
N6 H6A 0.87(2) . ?
N6 C45 1.46(3) . ?
C43 H43 0.9300 . ?
C43 C36 1.38(3) . ?
C43 C47 1.37(2) . ?
C40 C37 1.48(2) . ?
C40 C49 1.40(2) . ?
C40 C45 1.33(2) . ?
C42 C46 1.36(2) . ?
C42 C48 1.47(2) . ?
C42 C39 1.39(2) . ?
C46 C36 1.36(3) . ?
C41 H41 0.9300 . ?
C41 C44 1.37(3) . ?
C41 C38 1.34(3) . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C39 C47 1.34(3) . ?
C44 H44 0.9300 . ?
C44 C45 1.39(3) . ?
C36 H36 0.9300 . ?
C47 H47 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C49 C38 1.41(4) . ?
C38 H38 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
O3 C15 C16 C17 2.6(5) . . . . ?
O3 C15 C16 C21 -176.9(3) . . . . ?
O4 C15 C16 C17 -178.3(3) . . . . ?
O4 C15 C16 C21 2.2(5) . . . . ?
C15 C16 C17 C18 -178.7(4) . . . . ?
C15 C16 C21 C20 178.7(3) . . . . ?
C15 C16 C21 N2 8.3(6) . . . . ?
C15 C16 C21 N5 -18.7(10) . . . . ?
C16 C17 C18 C19 -0.5(7) . . . . ?
C16 C21 N2 C22 173.5(8) . . . . ?
C16 C21 N5 C46 -177.4(13) . . . . ?
C17 C16 C21 C20 -0.8(5) . . . . ?
C17 C16 C21 N2 -171.2(5) . . . . ?
C17 C16 C21 N5 161.8(9) . . . . ?
C17 C18 C19 C20 0.2(6) . . . . ?
C18 C19 C20 C21 -0.2(6) . . . . ?
C19 C20 C21 C16 0.5(5) . . . . ?
C19 C20 C21 N2 171.1(5) . . . . ?
C19 C20 C21 N5 -162.2(8) . . . . ?
C20 C21 N2 C22 3.3(12) . . . . ?
C20 C21 N5 C46 -15.2(19) . . . . ?
C21 C16 C17 C18 0.8(6) . . . . ?
C21 N2 C22 C23 74.1(11) . . . . ?
C21 N2 C22 C27 -105.8(12) . . . . ?
C21 N5 C46 C42 -84(2) . . . . ?
C21 N5 C46 C36 95(2) . . . . ?
Cl2 C24 C25 C26 -180.0(5) . . . . ?
N2 C22 C23 C24 178.4(9) . . . . ?
N2 C22 C23 C28 -0.8(17) . . . . ?
N2 C22 C27 C26 -177.8(11) . . . . ?
C22 C23 C24 Cl2 -179.6(6) . . . . ?
C22 C23 C24 C25 0.6(12) . . . . ?
C23 C22 C27 C26 2.3(16) . . . . ?
C23 C24 C25 C26 -0.2(14) . . . . ?
C24 C25 C26 C27 0.8(13) . . . . ?
C25 C26 C27 C22 -1.9(16) . . . . ?
C27 C22 C23 C24 -1.7(12) . . . . ?
C27 C22 C23 C28 179.1(13) . . . . ?
C28 C23 C24 Cl2 -0.3(15) . . . . ?
C28 C23 C24 C25 179.9(12) . . . . ?
O1 C1 C2 C3 169.2(3) . . . . ?
O1 C1 C2 C7 -10.0(5) . . . . ?
O2 C1 C2 C3 -11.0(5) . . . . ?
O2 C1 C2 C7 169.8(3) . . . . ?
C1 C2 C3 C4 -178.5(4) . . . . ?
C1 C2 C7 C6 179.3(3) . . . . ?
C1 C2 C7 N1 -11(3) . . . . ?
C1 C2 C7 N6 21(5) . . . . ?
C2 C3 C4 C5 -1.4(6) . . . . ?
C2 C7 N1 C8 -176(3) . . . . ?
C2 C7 N6 C45 178(5) . . . . ?
C3 C2 C7 C6 0.0(5) . . . . ?
C3 C2 C7 N1 170(3) . . . . ?
C3 C2 C7 N6 -158(5) . . . . ?
C3 C4 C5 C6 1.2(6) . . . . ?
C4 C5 C6 C7 -0.5(6) . . . . ?
C5 C6 C7 C2 -0.1(6) . . . . ?
C5 C6 C7 N1 -170(3) . . . . ?
C5 C6 C7 N6 159(5) . . . . ?
C6 C7 N1 C8 -6(6) . . . . ?
C6 C7 N6 C45 19(10) . . . . ?
C7 C2 C3 C4 0.8(5) . . . . ?
C7 N1 C8 C9 -71(5) . . . . ?
C7 N1 C8 C13 110(4) . . . . ?
C7 N6 C45 C40 80(7) . . . . ?
C7 N6 C45 C44 -105(8) . . . . ?
Cl1 C10 C11 C12 178.9(5) . . . . ?
N1 C8 C9 C10 -178.7(8) . . . . ?
N1 C8 C9 C14 2.3(14) . . . . ?
N1 C8 C13 C12 178.6(10) . . . . ?
C8 C9 C10 Cl1 -178.7(5) . . . . ?
C8 C9 C10 C11 -0.1(13) . . . . ?
C9 C8 C13 C12 -0.2(15) . . . . ?
C9 C10 C11 C12 0.3(14) . . . . ?
C10 C11 C12 C13 -0.4(12) . . . . ?
C11 C12 C13 C8 0.4(15) . . . . ?
C13 C8 C9 C10 0.0(11) . . . . ?
C13 C8 C9 C14 -178.9(11) . . . . ?
C14 C9 C10 Cl1 0.3(13) . . . . ?
C14 C9 C10 C11 178.9(11) . . . . ?
N3 C29 C30 C31 -179.1(3) . . . . ?
N3 C29 C33 C32 178.4(3) . . . . ?
N4 C32 C33 C29 1.9(5) . . . . ?
C29 C30 C31 N4 -0.5(5) . . . . ?
C30 C29 C33 C32 -3.0(5) . . . . ?
C31 N4 C32 C33 0.0(5) . . . . ?
C32 N4 C31 C30 -0.7(5) . . . . ?
C33 C29 C30 C31 2.4(5) . . . . ?
C34 N3 C29 C30 -1.5(5) . . . . ?
C34 N3 C29 C33 176.9(3) . . . . ?
C35 N3 C29 C30 178.2(3) . . . . ?
C35 N3 C29 C33 -3.3(4) . . . . ?
Cl3 C39 C47 C43 177.1(11) . . . . ?
Cl4 C49 C38 C41 179.2(14) . . . . ?
N5 C46 C36 C43 180(2) . . . . ?
C40 C49 C38 C41 -2(3) . . . . ?
C42 C46 C36 C43 -2(3) . . . . ?
C42 C39 C47 C43 1(3) . . . . ?
C46 C42 C39 Cl3 -179.8(10) . . . . ?
C46 C42 C39 C47 -4(2) . . . . ?
C41 C44 C45 N6 -178.3(19) . . . . ?
C41 C44 C45 C40 -3(3) . . . . ?
C48 C42 C46 N5 -2(3) . . . . ?
C48 C42 C46 C36 179(2) . . . . ?
C48 C42 C39 Cl3 5(2) . . . . ?
C48 C42 C39 C47 -179(2) . . . . ?
C39 C42 C46 N5 -177.5(17) . . . . ?
C39 C42 C46 C36 4(2) . . . . ?
C44 C41 C38 C49 1(3) . . . . ?
C36 C43 C47 C39 1(3) . . . . ?
C47 C43 C36 C46 -1(3) . . . . ?
C37 C40 C49 Cl4 2(2) . . . . ?
C37 C40 C49 C38 -177(2) . . . . ?
C37 C40 C45 N6 -6(3) . . . . ?
C37 C40 C45 C44 179(2) . . . . ?
C49 C40 C45 N6 176.9(17) . . . . ?
C49 C40 C45 C44 2(2) . . . . ?
C38 C41 C44 C45 1(3) . . . . ?
C45 C40 C49 Cl4 179.2(11) . . . . ?
C45 C40 C49 C38 0(2) . . . . ?
