#------------------------------------------------------------------------------
#$Date: 2024-05-25 00:30:35 +0200 (Sat 25 de May de 2024) $
#$Revision: 292017 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/86/7248675.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_7248675
loop_
_publ_author_name
'Breckell, Jaxon'
'Conte, Luke'
'Potts, Michael'
'Sawant, Pradnya'
'Butcher, R. J.'
'Vernekar, Beena K.'
'Richardson, Christopher'
_publ_section_title
;
 New diclofenac salts with the dense hydrogen bond donor
 propane-1,3-diaminium
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D4CE00397G
_journal_year                    2024
_chemical_formula_moiety
;
2(C14 H10 Cl2 N O2), C3 H12 N2, 3(H2 O)
;
_chemical_formula_sum            'C31 H38 Cl4 N4 O7'
_chemical_formula_weight         720.45
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-04-11 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.907(3)
_cell_angle_beta                 94.232(2)
_cell_angle_gamma                90.018(2)
_cell_formula_units_Z            2
_cell_length_a                   9.4328(2)
_cell_length_b                   9.8482(3)
_cell_length_c                   18.3159(7)
_cell_measurement_reflns_used    7015
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.3410
_cell_measurement_theta_min      2.1590
_cell_volume                     1696.62(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            32176
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.658
_diffrn_reflns_theta_min         2.068
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.401
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         9830
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0437
_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)+(0.0511P)²+0.1922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1116
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6574
_reflns_number_total             9830
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00397g2.cif
_cod_data_source_block           shelx
_cod_database_code               7248675
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1A Cl 0.94450(4) 0.21368(5) 0.96036(3) 0.02754(11) Uani 1 1 d . . . . .
Cl2A Cl 1.17197(5) 0.46867(5) 0.73511(3) 0.03343(12) Uani 1 1 d . . . . .
O1A O 0.92832(13) 0.23350(14) 0.64379(7) 0.0319(3) Uani 1 1 d . . . . .
O2A O 0.86223(15) 0.03908(15) 0.58787(8) 0.0366(3) Uani 1 1 d . . . . .
N1A N 0.96843(15) 0.27988(16) 0.79943(9) 0.0246(3) Uani 1 1 d . . . . .
H1AA H 0.991(2) 0.282(2) 0.7586(11) 0.029(6) Uiso 1 1 d . . . . .
C1A C 1.05423(17) 0.35393(17) 0.85042(10) 0.0224(4) Uani 1 1 d . . . . .
C2A C 1.05342(17) 0.33627(17) 0.92593(10) 0.0231(4) Uani 1 1 d . . . . .
C3A C 1.13948(18) 0.40990(19) 0.97625(11) 0.0270(4) Uani 1 1 d . . . . .
H3AA H 1.133052 0.397266 1.027212 0.032 Uiso 1 1 calc R U . . .
C4A C 1.23580(19) 0.5028(2) 0.95178(11) 0.0290(4) Uani 1 1 d . . . . .
H4AA H 1.294108 0.555475 0.985995 0.035 Uiso 1 1 calc R U . . .
C5A C 1.24625(18) 0.51825(19) 0.87759(11) 0.0286(4) Uani 1 1 d . . . . .
H5AA H 1.314304 0.578964 0.860535 0.034 Uiso 1 1 calc R U . . .
C6A C 1.15755(18) 0.44517(18) 0.82841(10) 0.0250(4) Uani 1 1 d . . . . .
C7A C 0.81861(17) 0.26711(18) 0.80168(10) 0.0225(4) Uani 1 1 d . . . . .
C8A C 0.74085(18) 0.35495(19) 0.84329(10) 0.0258(4) Uani 1 1 d . . . . .
H8AA H 0.787859 0.426983 0.870399 0.031 Uiso 1 1 calc R U . . .
C9A C 0.59502(18) 0.3385(2) 0.84565(10) 0.0281(4) Uani 1 1 d . . . . .
H9AA H 0.542859 0.398274 0.874779 0.034 Uiso 1 1 calc R U . . .
C10A C 0.52616(18) 0.2352(2) 0.80564(11) 0.0297(4) Uani 1 1 d . . . . .
H10A H 0.426460 0.223308 0.807087 0.036 Uiso 1 1 calc R U . . .
C11A C 0.60327(18) 0.14884(19) 0.76333(10) 0.0274(4) Uani 1 1 d . . . . .
H11A H 0.554979 0.078634 0.735346 0.033 Uiso 1 1 calc R U . . .
C12A C 0.75022(18) 0.16217(18) 0.76069(10) 0.0234(4) Uani 1 1 d . . . . .
C13A C 0.83134(19) 0.06216(18) 0.71631(10) 0.0253(4) Uani 1 1 d . . . . .
H13A H 0.771148 -0.019156 0.705662 0.030 Uiso 1 1 calc R U . . .
H13B H 0.917075 0.032964 0.746419 0.030 Uiso 1 1 calc R U . . .
C14A C 0.87701(19) 0.1161(2) 0.64470(11) 0.0287(4) Uani 1 1 d . . . . .
Cl1B Cl 0.54383(4) 0.71344(5) 0.96440(3) 0.02712(11) Uani 1 1 d . . . . .
Cl2B Cl 0.25806(5) 0.96587(5) 0.73646(3) 0.03306(12) Uani 1 1 d . . . . .
O1B O 0.46035(14) 0.74300(14) 0.64648(7) 0.0330(3) Uani 1 1 d . . . . .
O2B O 0.60747(15) 0.61707(15) 0.58527(8) 0.0375(3) Uani 1 1 d . . . . .
N1B N 0.48188(15) 0.78161(16) 0.80266(9) 0.0239(3) Uani 1 1 d . . . . .
H1BA H 0.4478(19) 0.7825(18) 0.7574(11) 0.020(5) Uiso 1 1 d . . . . .
C1B C 0.40735(17) 0.85418(17) 0.85292(10) 0.0218(4) Uani 1 1 d . . . . .
C2B C 0.42668(17) 0.83650(17) 0.92884(10) 0.0224(4) Uani 1 1 d . . . . .
C3B C 0.35222(18) 0.90976(19) 0.97848(11) 0.0261(4) Uani 1 1 d . . . . .
H3BA H 0.371031 0.896991 1.029583 0.031 Uiso 1 1 calc R U . . .
C4B C 0.24979(18) 1.0021(2) 0.95293(11) 0.0285(4) Uani 1 1 d . . . . .
H4BA H 0.199768 1.054713 0.986510 0.034 Uiso 1 1 calc R U . . .
C5B C 0.22085(18) 1.01719(18) 0.87833(11) 0.0270(4) Uani 1 1 d . . . . .
H5BA H 0.147723 1.076942 0.860435 0.032 Uiso 1 1 calc R U . . .
C6B C 0.29843(18) 0.94529(18) 0.83029(10) 0.0238(4) Uani 1 1 d . . . . .
C7B C 0.63241(17) 0.76984(18) 0.80635(10) 0.0219(4) Uani 1 1 d . . . . .
C8B C 0.72056(18) 0.85406(19) 0.85109(10) 0.0253(4) Uani 1 1 d . . . . .
H8BA H 0.680197 0.922376 0.880289 0.030 Uiso 1 1 calc R U . . .
C9B C 0.86703(19) 0.8393(2) 0.85351(11) 0.0291(4) Uani 1 1 d . . . . .
H9BA H 0.926435 0.896752 0.884661 0.035 Uiso 1 1 calc R U . . .
C10B C 0.92667(19) 0.7411(2) 0.81070(11) 0.0324(5) Uani 1 1 d . . . . .
H10B H 1.026938 0.730226 0.812600 0.039 Uiso 1 1 calc R U . . .
C11B C 0.83922(19) 0.6586(2) 0.76497(11) 0.0299(4) Uani 1 1 d . . . . .
H11B H 0.880619 0.592874 0.734565 0.036 Uiso 1 1 calc R U . . .
C12B C 0.69162(18) 0.67007(18) 0.76267(10) 0.0237(4) Uani 1 1 d . . . . .
C13B C 0.59836(19) 0.57717(19) 0.71331(10) 0.0273(4) Uani 1 1 d . . . . .
H13C H 0.514166 0.549720 0.738782 0.033 Uiso 1 1 calc R U . . .
H13D H 0.651856 0.494180 0.701504 0.033 Uiso 1 1 calc R U . . .
C14B C 0.55063(19) 0.64990(19) 0.64297(11) 0.0274(4) Uani 1 1 d . . . . .
O1W O 0.73751(17) 0.38509(16) 0.56141(9) 0.0385(4) Uani 1 1 d D . . . .
H1W1 H 0.710(3) 0.462(2) 0.5769(18) 0.120(14) Uiso 1 1 d D . . . .
H1W2 H 0.801(3) 0.364(3) 0.5941(14) 0.095(12) Uiso 1 1 d D . . . .
O2W O 0.56352(18) 0.97397(16) 0.57934(9) 0.0416(4) Uani 1 1 d D . . . .
H2W1 H 0.6512(18) 0.972(3) 0.5896(19) 0.114(14) Uiso 1 1 d D . . . .
H2W2 H 0.531(3) 0.907(2) 0.6011(14) 0.070(9) Uiso 1 1 d D . . . .
O3W O 0.80775(17) 0.35333(19) 0.41896(11) 0.0469(4) Uani 1 1 d D . . . .
H3W1 H 0.740(3) 0.313(3) 0.3951(15) 0.101(13) Uiso 1 1 d D . . . .
H3W2 H 0.771(3) 0.370(4) 0.4599(12) 0.123(15) Uiso 1 1 d D . . . .
N1S N 0.98228(17) 0.81511(18) 0.51734(10) 0.0334(4) Uani 1 1 d . . . . .
H1SA H 1.043766 0.762019 0.544789 0.052(7) Uiso 1 1 calc R . . . .
H1SB H 0.950176 0.883274 0.545888 0.071(9) Uiso 1 1 calc R . . . .
H1SC H 1.027725 0.851223 0.480027 0.064(8) Uiso 1 1 calc R . . . .
C2S C 0.8592(2) 0.7309(2) 0.48659(12) 0.0340(5) Uani 1 1 d . . . . .
H2SA H 0.800492 0.704248 0.526668 0.033(6) Uiso 1 1 calc R . . . .
H2SB H 0.894863 0.647069 0.463773 0.044(6) Uiso 1 1 calc R . . . .
C3S C 0.7682(2) 0.8094(2) 0.42974(12) 0.0365(5) Uani 1 1 d . . . . .
H3SA H 0.745491 0.899606 0.450475 0.046(7) Uiso 1 1 calc R . . . .
H3SB H 0.823105 0.824073 0.386520 0.042(6) Uiso 1 1 calc R . . . .
C4S C 0.6306(2) 0.7361(2) 0.40552(11) 0.0383(5) Uani 1 1 d . . . . .
H4SA H 0.593101 0.770742 0.357465 0.055(7) Uiso 1 1 calc R . . . .
H4SB H 0.649754 0.637843 0.399631 0.046(7) Uiso 1 1 calc R . . . .
N5S N 0.52187(17) 0.75634(17) 0.46012(9) 0.0320(4) Uani 1 1 d . . . . .
H5SA H 0.439842 0.713381 0.443872 0.043(7) Uiso 1 1 calc R . . . .
H5SB H 0.504841 0.846681 0.465901 0.055(7) Uiso 1 1 calc R . . . .
H5SC H 0.554760 0.721289 0.503819 0.045(7) Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A N1A C7A 123.87(16) . . ?
C1A N1A H1AA 115.5(15) . . ?
C7A N1A H1AA 111.5(15) . . ?
N1A C1A C2A 123.26(16) . . ?
N1A C1A C6A 121.26(16) . . ?
C2A C1A C6A 115.28(16) . . ?
C3A C2A C1A 122.90(16) . . ?
C3A C2A Cl1A 116.88(14) . . ?
C1A C2A Cl1A 120.20(14) . . ?
C2A C3A C4A 119.48(18) . . ?
C2A C3A H3AA 120.3 . . ?
C4A C3A H3AA 120.3 . . ?
C5A C4A C3A 119.72(18) . . ?
C5A C4A H4AA 120.1 . . ?
C3A C4A H4AA 120.1 . . ?
C6A C5A C4A 119.69(17) . . ?
C6A C5A H5AA 120.2 . . ?
C4A C5A H5AA 120.2 . . ?
C5A C6A C1A 122.74(17) . . ?
C5A C6A Cl2A 118.52(14) . . ?
C1A C6A Cl2A 118.73(14) . . ?
C8A C7A C12A 120.16(16) . . ?
C8A C7A N1A 121.84(17) . . ?
C12A C7A N1A 118.00(16) . . ?
C7A C8A C9A 120.63(18) . . ?
C7A C8A H8AA 119.7 . . ?
C9A C8A H8AA 119.7 . . ?
C10A C9A C8A 119.85(18) . . ?
C10A C9A H9AA 120.1 . . ?
C8A C9A H9AA 120.1 . . ?
C9A C10A C11A 119.53(16) . . ?
C9A C10A H10A 120.2 . . ?
C11A C10A H10A 120.2 . . ?
C10A C11A C12A 121.76(18) . . ?
C10A C11A H11A 119.1 . . ?
C12A C11A H11A 119.1 . . ?
C11A C12A C7A 118.06(17) . . ?
C11A C12A C13A 120.08(17) . . ?
C7A C12A C13A 121.83(15) . . ?
C12A C13A C14A 114.78(15) . . ?
C12A C13A H13A 108.6 . . ?
C14A C13A H13A 108.6 . . ?
C12A C13A H13B 108.6 . . ?
C14A C13A H13B 108.6 . . ?
H13A C13A H13B 107.5 . . ?
O1A C14A O2A 122.92(18) . . ?
O1A C14A C13A 118.82(18) . . ?
O2A C14A C13A 118.26(17) . . ?
C1B N1B C7B 124.26(15) . . ?
C1B N1B H1BA 116.8(12) . . ?
C7B N1B H1BA 110.3(12) . . ?
N1B C1B C2B 123.47(15) . . ?
N1B C1B C6B 121.53(16) . . ?
C2B C1B C6B 114.85(16) . . ?
C3B C2B C1B 123.00(16) . . ?
C3B C2B Cl1B 116.87(14) . . ?
C1B C2B Cl1B 120.08(14) . . ?
C2B C3B C4B 119.38(18) . . ?
C2B C3B H3BA 120.3 . . ?
C4B C3B H3BA 120.3 . . ?
C5B C4B C3B 119.73(18) . . ?
C5B C4B H4BA 120.1 . . ?
C3B C4B H4BA 120.1 . . ?
C6B C5B C4B 119.63(16) . . ?
C6B C5B H5BA 120.2 . . ?
C4B C5B H5BA 120.2 . . ?
C5B C6B C1B 123.22(17) . . ?
C5B C6B Cl2B 118.39(13) . . ?
C1B C6B Cl2B 118.38(14) . . ?
C8B C7B C12B 119.85(16) . . ?
C8B C7B N1B 122.15(16) . . ?
C12B C7B N1B 118.00(16) . . ?
C9B C8B C7B 120.56(18) . . ?
C9B C8B H8BA 119.7 . . ?
C7B C8B H8BA 119.7 . . ?
C10B C9B C8B 120.11(18) . . ?
C10B C9B H9BA 119.9 . . ?
C8B C9B H9BA 119.9 . . ?
C9B C10B C11B 119.51(17) . . ?
C9B C10B H10B 120.2 . . ?
C11B C10B H10B 120.2 . . ?
C10B C11B C12B 121.33(18) . . ?
C10B C11B H11B 119.3 . . ?
C12B C11B H11B 119.3 . . ?
C11B C12B C7B 118.62(17) . . ?
C11B C12B C13B 120.34(17) . . ?
C7B C12B C13B 121.03(15) . . ?
C12B C13B C14B 109.90(15) . . ?
C12B C13B H13C 109.7 . . ?
C14B C13B H13C 109.7 . . ?
C12B C13B H13D 109.7 . . ?
C14B C13B H13D 109.7 . . ?
H13C C13B H13D 108.2 . . ?
O1B C14B O2B 123.62(17) . . ?
O1B C14B C13B 117.98(17) . . ?
O2B C14B C13B 118.35(16) . . ?
H1W1 O1W H1W2 102(2) . . ?
H2W1 O2W H2W2 105(2) . . ?
H3W1 O3W H3W2 102(2) . . ?
C2S N1S H1SA 109.5 . . ?
C2S N1S H1SB 109.5 . . ?
H1SA N1S H1SB 109.5 . . ?
C2S N1S H1SC 109.5 . . ?
H1SA N1S H1SC 109.5 . . ?
H1SB N1S H1SC 109.5 . . ?
N1S C2S C3S 110.86(16) . . ?
N1S C2S H2SA 109.5 . . ?
C3S C2S H2SA 109.5 . . ?
N1S C2S H2SB 109.5 . . ?
C3S C2S H2SB 109.5 . . ?
H2SA C2S H2SB 108.1 . . ?
C4S C3S C2S 112.48(17) . . ?
C4S C3S H3SA 109.1 . . ?
C2S C3S H3SA 109.1 . . ?
C4S C3S H3SB 109.1 . . ?
C2S C3S H3SB 109.1 . . ?
H3SA C3S H3SB 107.8 . . ?
N5S C4S C3S 111.11(18) . . ?
N5S C4S H4SA 109.4 . . ?
C3S C4S H4SA 109.4 . . ?
N5S C4S H4SB 109.4 . . ?
C3S C4S H4SB 109.4 . . ?
H4SA C4S H4SB 108.0 . . ?
C4S N5S H5SA 109.5 . . ?
C4S N5S H5SB 109.5 . . ?
H5SA N5S H5SB 109.5 . . ?
C4S N5S H5SC 109.5 . . ?
H5SA N5S H5SC 109.5 . . ?
H5SB N5S H5SC 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
Cl1A C2A 1.7407(17) . ?
Cl2A C6A 1.7433(19) . ?
O1A C14A 1.254(2) . ?
O2A C14A 1.277(2) . ?
N1A C1A 1.388(2) . ?
N1A C7A 1.423(2) . ?
N1A H1AA 0.79(2) . ?
C1A C2A 1.397(2) . ?
C1A C6A 1.410(2) . ?
C2A C3A 1.379(2) . ?
C3A C4A 1.392(3) . ?
C3A H3AA 0.9500 . ?
C4A C5A 1.380(3) . ?
C4A H4AA 0.9500 . ?
C5A C6A 1.377(3) . ?
C5A H5AA 0.9500 . ?
C7A C8A 1.389(3) . ?
C7A C12A 1.397(3) . ?
C8A C9A 1.389(2) . ?
C8A H8AA 0.9500 . ?
C9A C10A 1.378(3) . ?
C9A H9AA 0.9500 . ?
C10A C11A 1.384(3) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.397(2) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.511(3) . ?
C13A C14A 1.514(3) . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
Cl1B C2B 1.7418(17) . ?
Cl2B C6B 1.7477(18) . ?
O1B C14B 1.256(2) . ?
O2B C14B 1.258(2) . ?
N1B C1B 1.388(2) . ?
N1B C7B 1.421(2) . ?
N1B H1BA 0.867(19) . ?
C1B C2B 1.402(2) . ?
C1B C6B 1.408(2) . ?
C2B C3B 1.384(2) . ?
C3B C4B 1.388(2) . ?
C3B H3BA 0.9500 . ?
C4B C5B 1.384(3) . ?
C4B H4BA 0.9500 . ?
C5B C6B 1.374(3) . ?
C5B H5BA 0.9500 . ?
C7B C8B 1.389(3) . ?
C7B C12B 1.400(2) . ?
C8B C9B 1.387(2) . ?
C8B H8BA 0.9500 . ?
C9B C10B 1.381(3) . ?
C9B H9BA 0.9500 . ?
C10B C11B 1.385(3) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.394(2) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.511(3) . ?
C13B C14B 1.523(2) . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
O1W H1W1 0.851(17) . ?
O1W H1W2 0.842(17) . ?
O2W H2W1 0.835(17) . ?
O2W H2W2 0.846(16) . ?
O3W H3W1 0.842(17) . ?
O3W H3W2 0.862(17) . ?
N1S C2S 1.497(2) . ?
N1S H1SA 0.9100 . ?
N1S H1SB 0.9100 . ?
N1S H1SC 0.9100 . ?
C2S C3S 1.521(3) . ?
C2S H2SA 0.9900 . ?
C2S H2SB 0.9900 . ?
C3S C4S 1.519(3) . ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C4S N5S 1.496(3) . ?
C4S H4SA 0.9900 . ?
C4S H4SB 0.9900 . ?
N5S H5SA 0.9100 . ?
N5S H5SB 0.9100 . ?
N5S H5SC 0.9100 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1AA Cl2A 0.79(2) 2.57(2) 2.9885(16) 114.4(17) . yes
N1A H1AA O1A 0.79(2) 2.19(2) 2.877(2) 145.8(19) . yes
N1B H1BA Cl2B 0.867(19) 2.556(18) 2.9857(15) 111.6(14) . yes
N1B H1BA O1B 0.867(19) 2.075(19) 2.872(2) 152.6(16) . yes
O1W H1W1 O2B 0.851(17) 1.819(18) 2.639(2) 161(3) . yes
O1W H1W2 O1A 0.842(17) 1.949(19) 2.723(2) 152(3) . yes
O2W H2W1 O2A 0.835(17) 2.098(18) 2.882(2) 156(3) 1_565 yes
O2W H2W2 O1B 0.846(16) 1.966(16) 2.810(2) 176(3) . yes
O3W H3W1 O1B 0.842(17) 2.06(2) 2.872(2) 162(3) 2_666 yes
O3W H3W2 O1W 0.862(17) 1.912(19) 2.752(3) 164(4) . yes
N1S H1SA O3W 0.91 1.89 2.785(2) 166.6 2_766 yes
N1S H1SB O2A 0.91 1.92 2.818(2) 168.3 1_565 yes
N1S H1SC O1A 0.91 2.47 3.158(2) 132.9 2_766 yes
N1S H1SC O2A 0.91 2.01 2.903(2) 168.6 2_766 yes
C2S H2SA O2B 0.99 2.35 3.295(2) 159.4 . yes
C3S H3SB O1A 0.99 2.51 3.277(2) 133.9 2_766 yes
N5S H5SA O1W 0.91 1.93 2.814(2) 163.8 2_666 yes
N5S H5SB O2W 0.91 2.44 3.040(2) 123.8 . yes
N5S H5SB O2W 0.91 2.05 2.864(2) 148.7 2_676 yes
N5S H5SC O2B 0.91 1.86 2.759(2) 168.5 . yes
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
C7A N1A C1A C2A 52.3(2) . . . . ?
C7A N1A C1A C6A -133.10(18) . . . . ?
N1A C1A C2A C3A 179.72(16) . . . . ?
C6A C1A C2A C3A 4.8(2) . . . . ?
N1A C1A C2A Cl1A 1.7(2) . . . . ?
C6A C1A C2A Cl1A -173.25(12) . . . . ?
C1A C2A C3A C4A -2.4(3) . . . . ?
Cl1A C2A C3A C4A 175.67(13) . . . . ?
C2A C3A C4A C5A -1.4(3) . . . . ?
C3A C4A C5A C6A 2.4(3) . . . . ?
C4A C5A C6A C1A 0.2(3) . . . . ?
C4A C5A C6A Cl2A 179.18(14) . . . . ?
N1A C1A C6A C5A -178.72(16) . . . . ?
C2A C1A C6A C5A -3.7(2) . . . . ?
N1A C1A C6A Cl2A 2.3(2) . . . . ?
C2A C1A C6A Cl2A 177.35(12) . . . . ?
C1A N1A C7A C8A 17.1(3) . . . . ?
C1A N1A C7A C12A -162.61(16) . . . . ?
C12A C7A C8A C9A 1.0(3) . . . . ?
N1A C7A C8A C9A -178.70(16) . . . . ?
C7A C8A C9A C10A -0.9(3) . . . . ?
C8A C9A C10A C11A -0.1(3) . . . . ?
C9A C10A C11A C12A 0.9(3) . . . . ?
C10A C11A C12A C7A -0.7(3) . . . . ?
C10A C11A C12A C13A 177.42(16) . . . . ?
C8A C7A C12A C11A -0.3(2) . . . . ?
N1A C7A C12A C11A 179.48(15) . . . . ?
C8A C7A C12A C13A -178.34(15) . . . . ?
N1A C7A C12A C13A 1.4(2) . . . . ?
C11A C12A C13A C14A 104.81(19) . . . . ?
C7A C12A C13A C14A -77.2(2) . . . . ?
C12A C13A C14A O1A 43.5(2) . . . . ?
C12A C13A C14A O2A -136.94(17) . . . . ?
C7B N1B C1B C2B -51.9(2) . . . . ?
C7B N1B C1B C6B 132.66(18) . . . . ?
N1B C1B C2B C3B 179.74(16) . . . . ?
C6B C1B C2B C3B -4.5(2) . . . . ?
N1B C1B C2B Cl1B -2.7(2) . . . . ?
C6B C1B C2B Cl1B 172.98(12) . . . . ?
C1B C2B C3B C4B 2.3(3) . . . . ?
Cl1B C2B C3B C4B -175.29(14) . . . . ?
C2B C3B C4B C5B 1.7(3) . . . . ?
C3B C4B C5B C6B -3.0(3) . . . . ?
C4B C5B C6B C1B 0.6(3) . . . . ?
C4B C5B C6B Cl2B 179.52(14) . . . . ?
N1B C1B C6B C5B 178.91(16) . . . . ?
C2B C1B C6B C5B 3.1(2) . . . . ?
N1B C1B C6B Cl2B 0.0(2) . . . . ?
C2B C1B C6B Cl2B -175.85(12) . . . . ?
C1B N1B C7B C8B -14.7(3) . . . . ?
C1B N1B C7B C12B 165.74(16) . . . . ?
C12B C7B C8B C9B -0.7(3) . . . . ?
N1B C7B C8B C9B 179.74(16) . . . . ?
C7B C8B C9B C10B 0.6(3) . . . . ?
C8B C9B C10B C11B 0.6(3) . . . . ?
C9B C10B C11B C12B -1.8(3) . . . . ?
C10B C11B C12B C7B 1.7(3) . . . . ?
C10B C11B C12B C13B -178.90(16) . . . . ?
C8B C7B C12B C11B -0.5(2) . . . . ?
N1B C7B C12B C11B 179.13(16) . . . . ?
C8B C7B C12B C13B -179.86(15) . . . . ?
N1B C7B C12B C13B -0.3(2) . . . . ?
C11B C12B C13B C14B -98.90(19) . . . . ?
C7B C12B C13B C14B 80.5(2) . . . . ?
C12B C13B C14B O1B -71.9(2) . . . . ?
C12B C13B C14B O2B 105.5(2) . . . . ?
N1S C2S C3S C4S -171.42(17) . . . . ?
C2S C3S C4S N5S 79.9(2) . . . . ?
