The solid-state conformation of the topical antifungal agent <i>O</i>-naphthalen-2-yl <i>N</i>-methyl-<i>N</i>-(3-methylphenyl)carbamothioate
Ho, Douglas M.; Zdilla, Michael J.; Acta Crystallographica Section C 74 (2018) –; doi:10.1107/S2053229618013591

data_2021308
_publ_section_title
;
 The solid-state conformation of the topical antifungal agent
 <i>O</i>-naphthalen-2-yl
 <i>N</i>-methyl-<i>N</i>-(3-methylphenyl)carbamothioate
;
_journal_coeditor_code           YP3169
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618013591
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C19 H17 N O S'
_chemical_formula_moiety         'C19 H17 N O S'
_chemical_formula_sum            'C19 H17 N O S'
_chemical_formula_weight         307.39
_chemical_name_common            Tolnaftate
_chemical_name_systematic
;
<i>O</i>-Naphthalen-2-yl
<i>N</i>-methyl-<i>N</i>-(3-methylphenyl)carbamothioate
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 117.3590(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.0498(11)
_cell_length_b                   5.7778(4)
_cell_length_c                   18.1012(11)
_cell_measurement_reflns_used    2309
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.67
_cell_measurement_theta_min      2.53
_cell_volume                     1583.70(18)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2013), SADABS (Bruker, 2014) and
XPREP (Bruker, 2014)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker Kappa APEXII DUO'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6795
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.923
_diffrn_reflns_theta_min         2.257
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9062
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'cut needle'
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.291
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.269
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3706
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0377
_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/[\s^2^(Fo^2^)+(0.0351P)^2^+0.7897P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0925
_reflns_number_gt                2935
_reflns_number_total             3706
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            yp3169sup1.cif
_cod_data_source_block           I
_cod_database_code               2021308
_shelx_estimated_absorpt_t_min   0.943
_shelx_estimated_absorpt_t_max   0.986
_shelx_hkl_checksum              33518
_shelx_res_checksum              20768
_cod_database_fobs_code 2021308