Halogen/methyl exchange in a series of isostructural 1,3-bis(m-dihalophenyl)ureas
Capacci-Daniel, Christina; Dehghan, Shoaleh; Wurster, Victoria M.; Basile, Joseph A.; Hiremath, Rupa; Sarjeant, Amy A.; Swift, Jennifer A.; CrystEngComm 10 (2008) 1875–; doi:10.1039/b812138a

data_7202429
_publ_section_title
;
 Halogen/methyl exchange in a series of isostructural
 1,3-bis(m-dihalophenyl)ureas
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              1875
_journal_paper_doi               10.1039/b812138a
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C14 H13 Cl N2 O'
_chemical_formula_sum            'C14 H13 Cl N2 O'
_chemical_formula_weight         260.71
_chemical_melting_point          235.3
_chemical_name_common            '1-(m-chlorophenyl)-3-(m-tolyl) urea'
_chemical_name_systematic        '1-(m-chlorophenyl)-3-(m-tolyl) urea'
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      18
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date
;
'Fri Jun 30 15:37:57 2006'
;
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.5777(5)
_cell_length_b                   14.3646(7)
_cell_length_c                   4.5596(2)
_cell_measurement_temperature    110
_cell_measurement_theta_max      28.4915
_cell_measurement_theta_min      4.2476
_cell_volume                     627.31(5)
_computing_cell_refinement       'Oxford Diffraction CrysAlis RED'
_computing_data_collection       'Oxford Diffraction CrysAlis CCD'
_computing_data_reduction        'Oxford Diffraction CrysAlis RED'
_computing_molecular_graphics    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_publication_material  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_refinement  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_solution    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_diffrn_ambient_temperature      110
_diffrn_detector_area_resol_mean 15.9890
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      'see scan set'
_diffrn_measurement_device       Kappa
_diffrn_measurement_device_type  Xcalibur3
_diffrn_measurement_method       ' omega scans'
_diffrn_orient_matrix_UB_11      -0.0189040031
_diffrn_orient_matrix_UB_12      0.0463916780
_diffrn_orient_matrix_UB_13      0.0380088770
_diffrn_orient_matrix_UB_21      -0.1056461910
_diffrn_orient_matrix_UB_22      0.0380503592
_diffrn_orient_matrix_UB_23      -0.0259155703
_diffrn_orient_matrix_UB_31      -0.1126077590
_diffrn_orient_matrix_UB_32      -0.0434104360
_diffrn_orient_matrix_UB_33      0.0179422285
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            9349
_diffrn_reflns_resolution_max    0.74
_diffrn_reflns_theta_full        28.55
_diffrn_reflns_theta_max         28.55
_diffrn_reflns_theta_min         4.47
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           40
_diffrn_source_power             2
_diffrn_source_voltage           50
_diffrn_standards_interval_count 1
_diffrn_standards_interval_time  50
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.5 (release 22-02-2006 CrysAlis171 .NET)
(compiled Feb 22 2006,13:01:44)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             272
_exptl_crystal_recrystallization_method benzene
_exptl_crystal_size_max          0.1923
_exptl_crystal_size_mid          0.0840
_exptl_crystal_size_min          0.0218
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     97
_refine_ls_number_reflns         1597
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0595P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1026
_reflns_number_gt                1387
_reflns_number_total             1597
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b812138a.txt
_cod_data_source_block           mClMePU
_cod_database_code               7202429
_audit_creation_method_reference
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.5 (release 22-02-2006 CrysAlis171 .NET)
(compiled Feb 22 2006,13:01:44)
;
_computing_data_collection_reference
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.29.5 (release 22-02-2006 CrysAlis171 .NET)
(compiled Feb 22 2006,13:01:44)
;
_computing_cell_refinment_reference
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.5 (release 22-02-2006 CrysAlis171 .NET)
(compiled Feb 22 2006,13:01:44)
;
_computing_data_reduction_reference
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.5 (release 22-02-2006 CrysAlis171 .NET)
(compiled Feb 22 2006,13:01:44)
;
_cell_measurement_resolution_max 0.74