Syntheses and structures of 1-[2,2-dichloro-1-hydroxy-3-(4-methylphenyl)-3-oxopropyl]urea and 1-[2,2-dichloro-3-(4-fluorophenyl)-1-hydroxy-3-oxopropyl]urea
Guseinov, Firudin I.; Hökelek, Tuncer; Afanaseva, Ksenia A.; Shuvalova, Elena V.; Glukhov, Lev M.; Samigullina, Aida I.; Belay, Alebel N.; Acta Crystallographica Section E Crystallographic Communications 81 (2025) –; doi:10.1107/S2056989025004359

data_2023513
_publ_section_title
;
 Syntheses and structures of
 1-[2,2-dichloro-1-hydroxy-3-(4-methylphenyl)-3-oxopropyl]urea and
 1-[2,2-dichloro-3-(4-fluorophenyl)-1-hydroxy-3-oxopropyl]urea
;
_journal_coeditor_code           HB8127
_journal_issue                   6
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989025004359
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          'C11 H12 Cl2 N2 O3'
_chemical_formula_moiety         'C11 H12 Cl2 N2 O3'
_chemical_formula_sum            'C11 H12 Cl2 N2 O3'
_chemical_formula_weight         291.13
_chemical_name_systematic
;
1-[2,2-Dichloro-3-(4-fluorophenyl)-1-hydroxy-3-oxopropyl]urea
;
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.8294(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.62183(13)
_cell_length_b                   8.77585(9)
_cell_length_c                   11.59930(11)
_cell_measurement_reflns_used    11708
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      80.3330
_cell_measurement_theta_min      3.5200
_cell_volume                     1280.26(2)
_computing_cell_refinement
;
CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)
;
_computing_data_collection
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction
;
CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)
;
_computing_molecular_graphics
;
Olex2 1.3 (Dolomanov et al., 2009)
;
_computing_publication_material
;
Olex2 1.3 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
<i>SHELXL2018/3</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT2014/5</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17344
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.733
_diffrn_reflns_theta_min         3.514
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    4.604
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.277
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2024)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.426
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0368
_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/[\s^2^(Fo^2^)+(0.0655P)^2^+0.6302P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1038
_reflns_number_gt                2738
_reflns_number_total             2808
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb8127.cif
_cod_data_source_block           II
_cod_database_code               2023513
_shelx_estimated_absorpt_t_min   0.231
_shelx_estimated_absorpt_t_max   0.526
_shelx_hkl_checksum              54128
_shelx_res_checksum              28237