#------------------------------------------------------------------------------
#$Date: 2019-11-22 19:30:57 +0200 (Fri, 22 Nov 2019) $
#$Revision: 231336 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/64/4516484.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_4516484
loop_
_publ_author_name
'Tahir, Muhammad Nawaz'
'Shafiq, Zahid'
'Shad, Hazoor Ahmad'
Zia-ur-Rehman,
'Karim, Abdul'
'Naseer, Muhammad Moazzam'
_publ_section_title
;
 Polymorphism in a Sulfamethoxazole Derivative: Coexistence of Five
 Polymorphs in Methanol at Room Temperature
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4750
_journal_paper_doi               10.1021/acs.cgd.5b01126
_journal_volume                  15
_journal_year                    2015
_chemical_formula_iupac          'C21 H17 N3 O4 S'
_chemical_formula_moiety         'C21 H17 N3 O4 S'
_chemical_formula_sum            'C21 H17 N3 O4 S'
_chemical_formula_weight         407.43
_chemical_name_systematic
;
1-[(E)-({4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl}iminio)methyl]
naphthalen-2-olate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 94.573(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1116(18)
_cell_length_b                   11.2257(15)
_cell_length_c                   14.8557(18)
_cell_measurement_reflns_used    2451
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.409
_cell_measurement_theta_min      1.687
_cell_volume                     2013.4(5)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.80
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17251
_diffrn_reflns_theta_full        27.409
_diffrn_reflns_theta_max         27.409
_diffrn_reflns_theta_min         1.687
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         4552
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.1173
_refine_ls_R_factor_gt           0.0517
_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)+(0.0502P)²+0.1307P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1278
_reflns_number_gt                2451
_reflns_number_total             4552
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg5b01126_si_002.cif
_cod_data_source_block           5
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4516484
_shelx_shelxl_version_number     2014/7
_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.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
S1 S 0.77324(5) 0.57470(5) -0.08420(4) 0.0536(2) Uani 1 1 d . .
O1 O 0.62943(17) -0.04110(18) 0.17924(13) 0.0845(6) Uani 1 1 d . .
O2 O 0.68578(14) 0.66076(14) -0.09152(12) 0.0677(5) Uani 1 1 d . .
O3 O 0.87558(14) 0.60116(14) -0.03464(11) 0.0640(5) Uani 1 1 d . .
O4 O 0.97004(18) 0.35174(18) -0.29195(14) 0.0837(6) Uani 1 1 d . .
N1 N 0.59017(18) 0.14108(17) 0.07610(13) 0.0514(5) Uani 1 1 d . .
H1 H 0.6389(19) 0.099(2) 0.1065(16) 0.062 Uiso 1 1 d . U
N2 N 0.79816(18) 0.54638(19) -0.18757(13) 0.0554(6) Uani 1 1 d . .
H2A H 0.744(2) 0.555(2) -0.2255(17) 0.066 Uiso 1 1 d . U
N3 N 0.87028(19) 0.4154(2) -0.28749(15) 0.0740(6) Uani 1 1 d . .
C1 C 0.5257(2) -0.0602(2) 0.17786(17) 0.0640(7) Uani 1 1 d . .
C2 C 0.4834(3) -0.1545(3) 0.22993(18) 0.0826(9) Uani 1 1 d . .
H2 H 0.5324 -0.2010 0.2663 0.099 Uiso 1 1 calc R U
C3 C 0.3749(3) -0.1771(3) 0.22727(18) 0.0776(9) Uani 1 1 d . .
H3 H 0.3507 -0.2390 0.2624 0.093 Uiso 1 1 calc R U
C4 C 0.2944(2) -0.1105(2) 0.17298(17) 0.0638(7) Uani 1 1 d . .
C5 C 0.1819(3) -0.1369(3) 0.1722(2) 0.0836(9) Uani 1 1 d . .
H5 H 0.1592 -0.1981 0.2088 0.100 Uiso 1 1 calc R U
C6 C 0.1051(3) -0.0759(3) 0.1197(3) 0.1002(11) Uani 1 1 d . .
H6 H 0.0304 -0.0950 0.1198 0.120 Uiso 1 1 calc R U
C7 C 0.1398(3) 0.0161(3) 0.0654(3) 0.1005(11) Uani 1 1 d . .
H7 H 0.0876 0.0585 0.0289 0.121 Uiso 1 1 calc R U
C8 C 0.2496(2) 0.0446(2) 0.0651(2) 0.0760(8) Uani 1 1 d . .
H8 H 0.2709 0.1055 0.0277 0.091 Uiso 1 1 calc R U
C9 C 0.3303(2) -0.0159(2) 0.11984(16) 0.0549(6) Uani 1 1 d . .
C10 C 0.4482(2) 0.0112(2) 0.12377(14) 0.0504(6) Uani 1 1 d . .
C11 C 0.4856(2) 0.1096(2) 0.07764(15) 0.0517(6) Uani 1 1 d . .
H11 H 0.4328 0.1564 0.0455 0.062 Uiso 1 1 calc R U
C12 C 0.6313(2) 0.2425(2) 0.03433(14) 0.0474(6) Uani 1 1 d . .
C13 C 0.5632(2) 0.3217(2) -0.01517(17) 0.0619(7) Uani 1 1 d . .
H13 H 0.4874 0.3076 -0.0233 0.074 Uiso 1 1 calc R U
C14 C 0.6076(2) 0.4213(2) -0.05233(17) 0.0605(7) Uani 1 1 d . .
H14 H 0.5620 0.4740 -0.0862 0.073 Uiso 1 1 calc R U
C15 C 0.7204(2) 0.44319(19) -0.03938(15) 0.0483(6) Uani 1 1 d . .
C16 C 0.7889(2) 0.3633(2) 0.00817(15) 0.0561(6) Uani 1 1 d . .
H16 H 0.8648 0.3770 0.0157 0.067 Uiso 1 1 calc R U
C17 C 0.7441(2) 0.2626(2) 0.04461(16) 0.0572(6) Uani 1 1 d . .
H17 H 0.7902 0.2081 0.0762 0.069 Uiso 1 1 calc R U
C18 C 0.8832(2) 0.4711(2) -0.21043(16) 0.0524(6) Uani 1 1 d . .
C19 C 0.9844(2) 0.4455(2) -0.16351(18) 0.0654(7) Uani 1 1 d . .
H19 H 1.0104 0.4735 -0.1068 0.078 Uiso 1 1 calc R U
C20 C 1.0361(2) 0.3726(3) -0.2168(2) 0.0744(8) Uani 1 1 d . .
C21 C 1.1463(3) 0.3141(3) -0.2090(2) 0.1129(12) Uani 1 1 d . .
H21A H 1.1916 0.3493 -0.1601 0.169 Uiso 1 1 calc R U
H21B H 1.1811 0.3246 -0.2643 0.169 Uiso 1 1 calc R U
H21C H 1.1374 0.2306 -0.1976 0.169 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
S S 0.1246 0.1234 '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
O3 S1 O2 120.51(11)
O3 S1 N2 108.14(10)
O2 S1 N2 104.66(11)
O3 S1 C15 107.92(11)
O2 S1 C15 107.78(11)
N2 S1 C15 107.14(10)
C20 O4 N3 109.2(2)
C11 N1 C12 126.9(2)
C11 N1 H1 117.5(16)
C12 N1 H1 115.4(16)
C18 N2 S1 123.13(17)
C18 N2 H2A 117.3(18)
S1 N2 H2A 115.0(18)
C18 N3 O4 104.0(2)
O1 C1 C2 120.7(3)
O1 C1 C10 121.2(2)
C2 C1 C10 118.1(3)
C3 C2 C1 121.2(3)
C3 C2 H2 119.4
C1 C2 H2 119.4
C2 C3 C4 122.9(3)
C2 C3 H3 118.5
C4 C3 H3 118.5
C5 C4 C9 120.0(3)
C5 C4 C3 121.1(3)
C9 C4 C3 118.9(3)
C6 C5 C4 121.6(3)
C6 C5 H5 119.2
C4 C5 H5 119.2
C5 C6 C7 118.9(3)
C5 C6 H6 120.5
C7 C6 H6 120.5
C8 C7 C6 120.8(3)
C8 C7 H7 119.6
C6 C7 H7 119.6
C7 C8 C9 121.3(3)
C7 C8 H8 119.3
C9 C8 H8 119.3
C8 C9 C4 117.3(2)
C8 C9 C10 124.1(2)
C4 C9 C10 118.6(2)
C11 C10 C1 119.6(2)
C11 C10 C9 120.1(2)
C1 C10 C9 120.2(2)
N1 C11 C10 124.9(2)
N1 C11 H11 117.5
C10 C11 H11 117.5
C17 C12 C13 119.8(2)
C17 C12 N1 117.8(2)
C13 C12 N1 122.5(2)
C14 C13 C12 120.0(2)
C14 C13 H13 120.0
C12 C13 H13 120.0
C13 C14 C15 120.1(2)
C13 C14 H14 120.0
C15 C14 H14 120.0
C16 C15 C14 120.1(2)
C16 C15 S1 121.18(19)
C14 C15 S1 118.70(18)
C15 C16 C17 119.6(2)
C15 C16 H16 120.2
C17 C16 H16 120.2
C12 C17 C16 120.4(2)
C12 C17 H17 119.8
C16 C17 H17 119.8
N3 C18 C19 112.4(2)
N3 C18 N2 117.7(2)
C19 C18 N2 129.9(2)
C20 C19 C18 105.5(2)
C20 C19 H19 127.3
C18 C19 H19 127.3
C19 C20 O4 109.0(3)
C19 C20 C21 133.6(3)
O4 C20 C21 117.4(3)
C20 C21 H21A 109.5
C20 C21 H21B 109.5
H21A C21 H21B 109.5
C20 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.4216(17)
S1 O2 1.4313(17)
S1 N2 1.620(2)
S1 C15 1.761(2)
O1 C1 1.273(3)
O4 C20 1.342(3)
O4 N3 1.410(3)
N1 C11 1.317(3)
N1 C12 1.407(3)
N1 H1 0.86(2)
N2 C18 1.395(3)
N2 H2A 0.84(2)
N3 C18 1.303(3)
C1 C2 1.430(3)
C1 C10 1.431(3)
C2 C3 1.336(4)
C2 H2 0.9300
C3 C4 1.426(4)
C3 H3 0.9300
C4 C5 1.393(4)
C4 C9 1.412(3)
C5 C6 1.352(4)
C5 H5 0.9300
C6 C7 1.396(4)
C6 H6 0.9300
C7 C8 1.368(4)
C7 H7 0.9300
C8 C9 1.397(4)
C8 H8 0.9300
C9 C10 1.456(3)
C10 C11 1.395(3)
C11 H11 0.9300
C12 C17 1.381(3)
C12 C13 1.384(3)
C13 C14 1.375(3)
C13 H13 0.9300
C14 C15 1.386(3)
C14 H14 0.9300
C15 C16 1.378(3)
C16 C17 1.382(3)
C16 H16 0.9300
C17 H17 0.9300
C18 C19 1.390(3)
C19 C20 1.329(3)
C19 H19 0.9300
C20 C21 1.483(4)
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
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
N1 H1 O1 0.86(2) 1.91(2) 2.577(3) 133(2) .
N2 H2A O1 0.84(2) 1.91(3) 2.729(3) 168(3) 4_565
C11 H11 O2 0.93 2.63 3.327(3) 132.6 3_665
C17 H17 N3 0.93 2.58 3.456(3) 157.4 4_566
C19 H19 O3 0.93 2.48 2.976(3) 113.6 .
C19 H19 O3 0.93 2.56 3.320(3) 138.9 3_765
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
O3 S1 N2 C18 46.5(2)
O2 S1 N2 C18 176.16(18)
C15 S1 N2 C18 -69.6(2)
C20 O4 N3 C18 0.5(3)
O1 C1 C2 C3 -178.4(3)
C10 C1 C2 C3 1.1(4)
C1 C2 C3 C4 0.3(5)
C2 C3 C4 C5 -180.0(3)
C2 C3 C4 C9 -0.3(4)
C9 C4 C5 C6 1.7(4)
C3 C4 C5 C6 -178.7(3)
C4 C5 C6 C7 -0.3(5)
C5 C6 C7 C8 -0.1(5)
C6 C7 C8 C9 -0.9(5)
C7 C8 C9 C4 2.2(4)
C7 C8 C9 C10 -179.0(3)
C5 C4 C9 C8 -2.6(4)
C3 C4 C9 C8 177.8(2)
C5 C4 C9 C10 178.6(2)
C3 C4 C9 C10 -1.0(3)
O1 C1 C10 C11 -5.5(4)
C2 C1 C10 C11 175.1(2)
O1 C1 C10 C9 177.0(2)
C2 C1 C10 C9 -2.4(3)
C8 C9 C10 C11 6.2(3)
C4 C9 C10 C11 -175.1(2)
C8 C9 C10 C1 -176.3(2)
C4 C9 C10 C1 2.4(3)
C12 N1 C11 C10 -176.6(2)
C1 C10 C11 N1 3.2(3)
C9 C10 C11 N1 -179.3(2)
C11 N1 C12 C17 176.7(2)
C11 N1 C12 C13 -2.7(3)
C17 C12 C13 C14 -1.3(4)
N1 C12 C13 C14 178.1(2)
C12 C13 C14 C15 -0.8(4)
C13 C14 C15 C16 2.2(4)
C13 C14 C15 S1 -177.47(19)
O3 S1 C15 C16 -22.3(2)
O2 S1 C15 C16 -153.95(18)
N2 S1 C15 C16 93.9(2)
O3 S1 C15 C14 157.32(18)
O2 S1 C15 C14 25.7(2)
N2 S1 C15 C14 -86.4(2)
C14 C15 C16 C17 -1.5(3)
S1 C15 C16 C17 178.17(17)
C13 C12 C17 C16 2.1(3)
N1 C12 C17 C16 -177.4(2)
C15 C16 C17 C12 -0.6(3)
O4 N3 C18 C19 -1.3(3)
O4 N3 C18 N2 177.82(19)
S1 N2 C18 N3 151.99(19)
S1 N2 C18 C19 -29.0(4)
N3 C18 C19 C20 1.6(3)
N2 C18 C19 C20 -177.4(2)
C18 C19 C20 O4 -1.2(3)
C18 C19 C20 C21 178.7(3)
N3 O4 C20 C19 0.5(3)
N3 O4 C20 C21 -179.4(2)
