#------------------------------------------------------------------------------
#$Date: 2022-01-07 01:33:21 +0200 (Fri, 07 Jan 2022) $
#$Revision: 271921 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/39/2243912.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_2243912
loop_
_publ_author_name
'Fujii, Isao'
_publ_section_title
;
 Crystal structure of nafamostat dimesylate
;
_journal_coeditor_code           TX2042
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              999
_journal_page_last               1002
_journal_paper_doi               10.1107/S2056989021009245
_journal_volume                  77
_journal_year                    2021
_chemical_compound_source        'see text'
_chemical_formula_iupac          'C19 H19 N5 O2 2+, 2C H3 O3 S -'
_chemical_formula_moiety         'C19 H19 N5 O2, 2(C H3 O3 S)'
_chemical_formula_sum            'C21 H25 N5 O8 S2'
_chemical_formula_weight         539.58
_chemical_name_systematic
'[Amino({6-[(4-{[amino(iminiumyl)methyl]amino}phenyl)carbonyloxy]naphthalen-2-yl})methylidene]azanium bis(methanesulfonate)'
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 96.7460(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.06310(10)
_cell_length_b                   9.72150(10)
_cell_length_c                   21.9271(3)
_cell_measurement_reflns_used    17552
_cell_measurement_temperature    95(2)
_cell_measurement_theta_max      73.45
_cell_measurement_theta_min      4.96
_cell_volume                     2341.93(5)
_computing_cell_refinement
;
Crysalis PRO (Rigaku, 2015)
;
_computing_data_collection
;
Crysalis PRO (Rigaku, 2015)
;
_computing_data_reduction
;
SORTAV (Blessing, 1995)
;
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 2012), Mercury
(Macrae et al., 2020)
;
_computing_publication_material
;
Platon (Spek, 2020), WinGX (Farrugia, 2012) and publCIF
(Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      95(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'quarter Χ-circle diffractometer'
_diffrn_measurement_device_type  'a Rigaku XtaLAB P200 diffractometer'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.058
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4675
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.836
_diffrn_reflns_theta_min         4.024
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.586
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.46
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku, 2015)
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.53
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       octahedron
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.636
_refine_diff_density_min         -0.518
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4675
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0324P)²+4.9921P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1259
_reflns_number_gt                4457
_reflns_number_total             4675
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tx2042sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2243912.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243912
_cod_database_fobs_code          2243912
_shelx_estimated_absorpt_t_min   0.424
_shelx_estimated_absorpt_t_max   0.782
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1422(2) 0.5583(3) 0.56523(13) 0.0225(5) Uani d 1 . .
C C2 0.0580(2) 0.5892(3) 0.60620(13) 0.0237(5) Uani d 1 . .
H H2 0.061778 0.544066 0.644799 0.028 Uiso calc 1 . .
C C3 -0.0304(2) 0.6865(3) 0.58945(12) 0.0234(5) Uani d 1 . .
H H3 -0.086637 0.710328 0.617287 0.028 Uiso calc 1 . .
C C4 -0.0384(2) 0.7505(3) 0.53201(12) 0.0225(5) Uani d 1 . .
C C5 -0.1241(2) 0.8550(3) 0.51578(12) 0.0229(5) Uani d 1 . .
H H5 -0.177017 0.883065 0.544597 0.027 Uiso calc 1 . .
C C6 -0.1333(2) 0.9184(3) 0.45831(13) 0.0229(5) Uani d 1 . .
C C7 -0.0545(2) 0.8762(3) 0.41562(12) 0.0237(5) Uani d 1 . .
H H7 -0.060246 0.917718 0.376162 0.028 Uiso calc 1 . .
C C8 0.0302(2) 0.7756(3) 0.43105(12) 0.0228(5) Uani d 1 . .
H H8 0.081746 0.747936 0.401556 0.027 Uiso calc 1 . .
C C9 0.0437(2) 0.7116(3) 0.48926(12) 0.0221(5) Uani d 1 . .
C C10 0.1352(2) 0.6151(3) 0.50758(12) 0.0224(5) Uani d 1 . .
H H10 0.191808 0.589251 0.480271 0.027 Uiso calc 1 . .
C C12 0.3080(2) 0.4764(3) 0.63457(12) 0.0205(5) Uani d 1 . .
C C14 -0.2214(2) 1.0326(3) 0.44424(12) 0.0203(5) Uani d 1 . .
C C16 0.4005(2) 0.3658(3) 0.64313(12) 0.0206(5) Uani d 1 . .
C C17 0.4753(2) 0.3600(3) 0.69882(12) 0.0223(5) Uani d 1 . .
H H17 0.466534 0.426978 0.729554 0.027 Uiso calc 1 . .
C C18 0.5632(2) 0.2563(3) 0.70998(12) 0.0222(5) Uani d 1 . .
H H18 0.61345 0.252049 0.748167 0.027 Uiso calc 1 . .
C C19 0.5758(2) 0.1599(3) 0.66434(12) 0.0217(5) Uani d 1 . .
C C20 0.5019(2) 0.1658(3) 0.60820(12) 0.0237(5) Uani d 1 . .
H H20 0.51147 0.100093 0.577062 0.028 Uiso calc 1 . .
C C21 0.4145(2) 0.2678(3) 0.59814(12) 0.0229(5) Uani d 1 . .
H H21 0.363537 0.271047 0.560152 0.027 Uiso calc 1 . .
C C24 0.7756(2) 0.0499(3) 0.69864(12) 0.0212(5) Uani d 1 . .
C C30 0.7107(2) 0.5832(3) 0.76962(13) 0.0245(6) Uani d 1 . .
H H30A 0.661242 0.637008 0.738122 0.037 Uiso calc 1 . .
H H30B 0.734263 0.641357 0.805571 0.037 Uiso calc 1 . .
H H30C 0.663287 0.504665 0.781635 0.037 Uiso calc 1 . .
C C35 0.6293(2) -0.4167(3) 0.57039(13) 0.0262(6) Uani d 1 . .
H H35A 0.717501 -0.403331 0.578279 0.039 Uiso calc 1 . .
H H35B 0.607172 -0.441466 0.527188 0.039 Uiso calc 1 . .
H H35C 0.604676 -0.490755 0.596665 0.039 Uiso calc 1 . .
N N15 -0.3033(2) 1.0565(3) 0.48204(11) 0.0238(5) Uani d 1 . .
N N22 -0.2175(2) 1.1128(2) 0.39642(11) 0.0214(5) Uani d 1 . .
N N23 0.65733(19) 0.0475(2) 0.67377(11) 0.0242(5) Uani d 1 . .
N N25 0.8365(2) 0.1631(2) 0.71094(12) 0.0242(5) Uani d 1 . .
N N26 0.8283(2) -0.0718(2) 0.70825(12) 0.0252(5) Uani d 1 . .
O O11 0.23387(15) 0.46189(19) 0.57993(8) 0.0217(4) Uani d 1 . .
O O13 0.29656(16) 0.5684(2) 0.67019(9) 0.0255(4) Uani d 1 . .
O O28 0.80155(16) 0.44602(19) 0.68474(8) 0.0234(4) Uani d 1 . .
O O29 0.91327(16) 0.64512(19) 0.72854(9) 0.0252(4) Uani d 1 . .
O O31 0.90733(15) 0.43603(19) 0.78786(8) 0.0221(4) Uani d 1 . .
O O33 0.42506(16) -0.2921(2) 0.57331(10) 0.0308(5) Uani d 1 . .
O O34 0.59193(17) -0.1572(2) 0.54595(9) 0.0282(4) Uani d 1 . .
O O36 0.59191(19) -0.2314(2) 0.65057(9) 0.0308(4) Uani d 1 . .
S S27 0.84252(5) 0.52334(6) 0.73995(3) 0.01897(15) Uani d 1 . .
S S32 0.55448(5) -0.26334(6) 0.58663(3) 0.01882(15) Uani d 1 . .
H H22A -0.168(3) 1.102(3) 0.3710(14) 0.017(7) Uiso d 1 . .
H H25B 0.902(3) 0.162(3) 0.7333(14) 0.019(7) Uiso d 1 . .
H H22B -0.266(3) 1.177(3) 0.3897(13) 0.019(7) Uiso d 1 . .
H H25A 0.806(3) 0.244(4) 0.7016(17) 0.039(10) Uiso d 1 . .
H H26B 0.787(3) -0.150(4) 0.7025(17) 0.045(10) Uiso d 1 . .
H H15A -0.354(3) 1.132(4) 0.4725(17) 0.043(10) Uiso d 1 . .
H H26A 0.905(4) -0.078(4) 0.7167(18) 0.051(11) Uiso d 1 . .
H H15B -0.323(3) 0.994(4) 0.5063(18) 0.043(10) Uiso d 1 . .
H H23 0.627(4) -0.042(5) 0.6577(19) 0.062(12) Uiso d 1 . .
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
S S 0.3331 0.5567 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 C1 O11 . . 116.5(2) ?
C10 C1 C2 . . 122.3(2) ?
O11 C1 C2 . . 121.2(2) ?
C3 C2 C1 . . 118.7(2) ?
C3 C2 H2 . . 120.6 ?
C1 C2 H2 . . 120.6 ?
C2 C3 C4 . . 120.8(2) ?
C2 C3 H3 . . 119.6 ?
C4 C3 H3 . . 119.6 ?
C3 C4 C5 . . 121.2(2) ?
C3 C4 C9 . . 119.7(2) ?
C5 C4 C9 . . 119.1(2) ?
C6 C5 C4 . . 121.5(2) ?
C6 C5 H5 . . 119.3 ?
C4 C5 H5 . . 119.3 ?
C5 C6 C7 . . 119.0(2) ?
C5 C6 C14 . . 119.6(2) ?
C7 C6 C14 . . 121.3(2) ?
C8 C7 C6 . . 120.1(2) ?
C8 C7 H7 . . 120 ?
C6 C7 H7 . . 120 ?
C7 C8 C9 . . 122.3(2) ?
C7 C8 H8 . . 118.8 ?
C9 C8 H8 . . 118.8 ?
C10 C9 C8 . . 123.3(2) ?
C10 C9 C4 . . 118.7(2) ?
C8 C9 C4 . . 117.9(2) ?
C1 C10 C9 . . 119.6(2) ?
C1 C10 H10 . . 120.2 ?
C9 C10 H10 . . 120.2 ?
O13 C12 O11 . . 122.9(2) ?
O13 C12 C16 . . 125.5(2) ?
O11 C12 C16 . . 111.6(2) ?
N22 C14 N15 . . 119.1(2) ?
N22 C14 C6 . . 121.9(2) ?
N15 C14 C6 . . 119.0(2) ?
C17 C16 C21 . . 119.3(2) ?
C17 C16 C12 . . 118.1(2) ?
C21 C16 C12 . . 122.6(2) ?
C16 C17 C18 . . 120.7(2) ?
C16 C17 H17 . . 119.7 ?
C18 C17 H17 . . 119.7 ?
C19 C18 C17 . . 119.0(2) ?
C19 C18 H18 . . 120.5 ?
C17 C18 H18 . . 120.5 ?
C18 C19 C20 . . 120.6(2) ?
C18 C19 N23 . . 122.1(2) ?
C20 C19 N23 . . 117.2(2) ?
C21 C20 C19 . . 119.7(3) ?
C21 C20 H20 . . 120.2 ?
C19 C20 H20 . . 120.2 ?
C20 C21 C16 . . 120.7(3) ?
C20 C21 H21 . . 119.6 ?
C16 C21 H21 . . 119.6 ?
N25 C24 N26 . . 121.0(2) ?
N25 C24 N23 . . 123.3(2) ?
N26 C24 N23 . . 115.7(2) ?
S27 C30 H30A . . 109.5 ?
S27 C30 H30B . . 109.5 ?
H30A C30 H30B . . 109.5 ?
S27 C30 H30C . . 109.5 ?
H30A C30 H30C . . 109.5 ?
H30B C30 H30C . . 109.5 ?
S32 C35 H35A . . 109.5 ?
S32 C35 H35B . . 109.5 ?
H35A C35 H35B . . 109.5 ?
S32 C35 H35C . . 109.5 ?
H35A C35 H35C . . 109.5 ?
H35B C35 H35C . . 109.5 ?
C14 N15 H15A . . 116(2) ?
C14 N15 H15B . . 120(3) ?
H15A N15 H15B . . 121(3) ?
C14 N22 H22A . . 123(2) ?
C14 N22 H22B . . 121(2) ?
H22A N22 H22B . . 116(3) ?
C24 N23 C19 . . 127.7(2) ?
C24 N23 H23 . . 115(2) ?
C19 N23 H23 . . 117(2) ?
C24 N25 H25B . . 121(2) ?
C24 N25 H25A . . 122(2) ?
H25B N25 H25A . . 116(3) ?
C24 N26 H26B . . 122(2) ?
C24 N26 H26A . . 120(3) ?
H26B N26 H26A . . 117(4) ?
C12 O11 C1 . . 118.4(2) ?
O28 S27 O29 . . 113.51(11) ?
O28 S27 O31 . . 112.04(11) ?
O29 S27 O31 . . 111.41(11) ?
O28 S27 C30 . . 106.72(12) ?
O29 S27 C30 . . 106.21(12) ?
O31 S27 C30 . . 106.39(12) ?
O36 S32 O33 . . 113.48(13) ?
O36 S32 O34 . . 111.82(12) ?
O33 S32 O34 . . 110.96(12) ?
O36 S32 C35 . . 106.84(13) ?
O33 S32 C35 . . 105.73(12) ?
O34 S32 C35 . . 107.57(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O11 . 1.391(3) y
C1 C2 . 1.401(4) ?
C1 C10 . 1.373(4) ?
C10 H10 . 0.95 ?
C12 O13 . 1.204(3) y
C12 O11 . 1.377(3) y
C12 C16 . 1.481(3) ?
C14 N22 . 1.311(3) y
C14 N15 . 1.319(3) y
C16 C21 . 1.393(4) ?
C16 C17 . 1.393(4) ?
C17 H17 . 0.95 ?
C17 C18 . 1.402(4) ?
C18 H18 . 0.95 ?
C18 C19 . 1.390(4) ?
C19 N23 . 1.417(3) y
C19 C20 . 1.397(4) ?
C2 H2 . 0.95 ?
C2 C3 . 1.379(4) ?
C20 H20 . 0.95 ?
C20 C21 . 1.384(4) ?
C21 H21 . 0.95 ?
C24 N26 . 1.325(3) y
C24 N25 . 1.302(4) y
C24 N23 . 1.357(3) y
C3 H3 . 0.95 ?
C3 C4 . 1.398(4) ?
C30 S27 . 1.764(3) y
C30 H30C . 0.98 ?
C30 H30B . 0.98 ?
C30 H30A . 0.98 ?
C35 S32 . 1.762(3) y
C35 H35C . 0.98 ?
C35 H35B . 0.98 ?
C35 H35A . 0.98 ?
C4 C9 . 1.430(4) ?
C4 C5 . 1.407(4) ?
C5 H5 . 0.95 ?
C5 C6 . 1.396(4) ?
C6 C7 . 1.413(4) ?
C6 C14 . 1.486(3) ?
C7 H7 . 0.95 ?
C7 C8 . 1.369(4) ?
C8 H8 . 0.95 ?
C8 C9 . 1.412(4) ?
C9 C10 . 1.403(4) ?
N15 H15B . 0.85(4) ?
N15 H15A . 0.93(4) ?
N22 H22B . 0.83(3) ?
N22 H22A . 0.83(3) ?
N23 H23 . 0.99(4) ?
N25 H25B . 0.83(3) ?
N25 H25A . 0.87(4) ?
N26 H26B . 0.89(4) ?
N26 H26A . 0.85(4) ?
O28 S27 . 1.4515(19) y
O29 S27 . 1.4570(19) y
O31 S27 . 1.4700(18) y
O33 S32 . 1.4545(18) y
O34 S32 . 1.4553(19) y
O36 S32 . 1.448(2) y
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C18 H18 O13 2_646 0.95 2.64 3.419(3) 139.7 yes
C30 H30A O36 1_565 0.98 2.36 3.314(3) 164.6 yes
N15 H15A O33 3_566 0.93(4) 1.97(4) 2.854(3) 159(3) yes
N15 H15A O34 3_566 0.93(4) 2.63(4) 3.327(3) 132(3) yes
N15 H15A S32 3_566 0.93(4) 2.75(4) 3.612(2) 154(3) yes
N15 H15B O34 1_465 0.85(4) 2.00(4) 2.830(3) 164(4) yes
N22 H22A O31 4_475 0.83(3) 2.12(3) 2.928(3) 162(3) yes
N22 H22B O33 3_566 0.83(3) 2.31(3) 3.018(3) 144(3) yes
N23 H23 O36 . 0.99(4) 1.88(5) 2.836(3) 163(4) yes
N23 H23 S32 . 0.99(4) 2.72(4) 3.683(2) 166(3) yes
N25 H25A O28 . 0.87(4) 2.00(4) 2.827(3) 159(3) yes
N25 H25A S27 . 0.87(4) 2.86(4) 3.558(2) 139(3) yes
N25 H25B O29 2_746 0.83(3) 2.12(3) 2.931(3) 167(3) yes
N26 H26A O31 2_746 0.85(4) 2.10(4) 2.916(3) 163(4) yes
N26 H26A S27 2_746 0.85(4) 3.01(4) 3.799(2) 156(3) yes
N26 H26B O29 1_545 0.89(4) 2.46(4) 2.925(3) 113(3) yes
N26 H26B O36 . 0.89(4) 2.45(4) 3.174(3) 139(3) yes
C30 H30B Cg(C) 1_545 0.98 2.96 3.405(3) 109 yes
