Crystal structures of (<i>S</i>)-(+)-5-(3-bromo/chloro-4-isopropoxyphenyl)-5-methylimidazolidine-2,4-dione
Ohba, Shigeru; Koura, Minoru; Sumida, Hisashi; Shibuya, Kimiyuki; Acta Crystallographica Section E 72 (2016) 184–187; doi:10.1107/S2056989015023014

data_2241471
_publ_section_title
;
 Crystal structures of
 (<i>S</i>)-(+)-5-(3-bromo/chloro-4-isopropoxyphenyl)-5-methylimidazolidine-2,4-dione
;
_journal_coeditor_code           SJ5484
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              184
_journal_page_last               187
_journal_paper_doi               10.1107/S2056989015023014
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C13 H15 Br N2 O3'
_chemical_formula_moiety         'C13 H15 Br N2 O3'
_chemical_formula_sum            'C13 H15 Br N2 O3'
_chemical_formula_weight         327.17
_chemical_melting_point_gt       480
_chemical_melting_point_lt       485
_chemical_name_systematic
;
(<i>S</i>)-(+)-5-(3-Bromo-4-isopropoxyphenyl)-5-methylimidazolidine-2,4-dione
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1840(3)
_cell_length_b                   9.6495(4)
_cell_length_c                   23.1111(10)
_cell_measurement_reflns_used    9747
_cell_measurement_temperature    90.0(10)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      2.75
_cell_volume                     1379.10(11)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>, 2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      90.0(10)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            31000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.913
_diffrn_reflns_theta_min         2.287
_exptl_absorpt_coefficient_mu    2.986
_exptl_absorpt_correction_T_max  0.6309
_exptl_absorpt_correction_T_min  0.4823
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.300
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1301 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>, 2013).
;
_refine_ls_abs_structure_Flack   0.018(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.294
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3271
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.294
_refine_ls_R_factor_all          0.0180
_refine_ls_R_factor_gt           0.0173
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0213P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0469
_refine_ls_wR_factor_ref         0.0474
_reflns_number_gt                3206
_reflns_number_total             3271
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sj5484sup1.cif
_cod_data_source_block           I
_cod_database_code               2241471
_shelx_estimated_absorpt_t_min   0.461
_shelx_estimated_absorpt_t_max   0.540
_shelx_hkl_checksum              5057
_shelx_res_checksum              21806