#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/59/2235934.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2235934
loop_
_publ_author_name
'Yu, Jian-Guang'
'Zhu, Hai-Xi'
'Qiu, Jiang-Kai'
'Wang, De-Cai'
'Xu, Hong'
_publ_section_title
;
 N-(2,4-Difluorophenyl)-5-methyl-1,2-oxazole-4-carboxamide
 hemihydrate
;
_journal_coeditor_code           NK2167
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2325
_journal_paper_doi               10.1107/S1600536812029431
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C11 H8 F2 N2 O2, 0.5H2 O'
_chemical_formula_moiety         'C11 H8 F2 N2 O2, 0.5(H2 O)'
_chemical_formula_sum            'C11 H9 F2 N2 O2.5'
_chemical_formula_weight         247.20
_chemical_name_systematic
;
N-(2,4-Difluorophenyl)-5-methyl-1,2-oxazole-4-carboxamide hemihydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 120.06(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.182(3)
_cell_length_b                   13.803(3)
_cell_length_c                   12.159(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     2205.3(10)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2076
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         2.14
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  0.9872
_exptl_absorpt_correction_T_min  0.9623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.179
_refine_ls_extinction_coef       0.0247(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         1997
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0600P)²+1.6000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1299
_reflns_number_gt                1486
_reflns_number_total             1997
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nk2167.cif
_cod_data_source_block           I
_cod_original_cell_volume        2205.3(8)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2235934
_cod_database_fobs_code          2235934
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1W 0.5000 0.52321(17) 0.2500 0.0620(7) Uani d S 1 2 A 4
H H1W 0.505(2) 0.564(2) 0.193(3) 0.093 Uiso d . 1 1 B 4
N N1 0.65863(15) 0.36286(13) 0.32726(18) 0.0484(5) Uani d . 1 1 C 4
H H1A 0.6314(18) 0.4180(19) 0.332(2) 0.058 Uiso d . 1 1 D 4
O O1 0.66094(13) 0.20060(11) 0.36060(16) 0.0611(5) Uani d . 1 1 C 4
F F1 0.88573(17) 0.40738(15) 0.0910(2) 0.1141(8) Uani d . 1 1 C 4
C C1 0.75004(19) 0.28877(17) 0.2259(2) 0.0584(6) Uani d . 1 1 C 4
H H1B 0.7336 0.2263 0.2381 0.070 Uiso calc R 1 1 C 4
F F2 0.71615(12) 0.53616(10) 0.28913(16) 0.0739(5) Uani d . 1 1 C 4
O O2 0.49066(13) 0.27282(12) 0.53567(16) 0.0615(5) Uani d . 1 1 C 4
N N2 0.51344(18) 0.37236(15) 0.5487(2) 0.0658(6) Uani d . 1 1 C 4
C C2 0.8072(2) 0.3024(2) 0.1673(3) 0.0720(8) Uani d . 1 1 C 4
H H2B 0.8293 0.2495 0.1403 0.086 Uiso calc R 1 1 C 4
C C3 0.8304(2) 0.3937(2) 0.1496(3) 0.0720(8) Uani d . 1 1 C 4
C C4 0.80009(19) 0.47406(19) 0.1878(2) 0.0649(7) Uani d . 1 1 C 4
H H4A 0.8162 0.5362 0.1742 0.078 Uiso calc R 1 1 C 4
C C5 0.74512(18) 0.45851(16) 0.2468(2) 0.0530(6) Uani d . 1 1 C 4
C C6 0.71701(16) 0.36750(15) 0.2668(2) 0.0461(5) Uani d . 1 1 C 4
C C7 0.63608(16) 0.28191(15) 0.37245(19) 0.0454(5) Uani d . 1 1 C 4
C C8 0.57905(16) 0.30012(15) 0.43950(19) 0.0450(5) Uani d . 1 1 C 4
C C9 0.56469(19) 0.38588(17) 0.4907(2) 0.0556(6) Uani d . 1 1 C 4
H H9A 0.5893 0.4460 0.4838 0.067 Uiso calc R 1 1 C 4
C C10 0.53140(17) 0.23129(16) 0.4714(2) 0.0492(6) Uani d . 1 1 C 4
C C11 0.5167(2) 0.12579(18) 0.4509(3) 0.0674(7) Uani d . 1 1 C 4
H H11A 0.4739 0.1028 0.4827 0.101 Uiso calc PR 0.48(6) 1 E 1
H H11B 0.5815 0.0938 0.4950 0.101 Uiso calc PR 0.48(6) 1 E 1
H H11C 0.4850 0.1121 0.3617 0.101 Uiso calc PR 0.48(6) 1 E 1
H H11D 0.5423 0.1049 0.3970 0.101 Uiso d PR 0.52(6) 1 E 2
H H11E 0.4454 0.1109 0.4112 0.101 Uiso d PR 0.52(6) 1 E 2
H H11F 0.5526 0.0929 0.5311 0.101 Uiso d PR 0.52(6) 1 E 2
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'
F F 0.0171 0.0103 '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
C7 N1 C6 126.79(19)
C7 N1 H1A 117.3(16)
C6 N1 H1A 115.8(16)
C2 C1 C6 120.6(2)
C2 C1 H1B 119.7
C6 C1 H1B 119.7
C10 O2 N2 108.88(17)
C9 N2 O2 105.04(18)
C3 C2 C1 119.3(2)
C3 C2 H2B 120.4
C1 C2 H2B 120.4
C2 C3 F1 119.4(3)
C2 C3 C4 122.8(2)
F1 C3 C4 117.8(2)
C5 C4 C3 116.7(2)
C5 C4 H4A 121.6
C3 C4 H4A 121.6
F2 C5 C4 118.5(2)
F2 C5 C6 117.62(19)
C4 C5 C6 123.9(2)
C5 C6 C1 116.6(2)
C5 C6 N1 117.51(19)
C1 C6 N1 125.85(19)
O1 C7 N1 123.6(2)
O1 C7 C8 121.66(19)
N1 C7 C8 114.70(18)
C10 C8 C9 103.82(19)
C10 C8 C7 125.4(2)
C9 C8 C7 130.7(2)
N2 C9 C8 112.8(2)
N2 C9 H9A 123.6
C8 C9 H9A 123.6
O2 C10 C8 109.43(19)
O2 C10 C11 116.39(19)
C8 C10 C11 134.2(2)
H11D C11 H11E 109.5
H11D C11 H11F 109.5
H11E C11 H11F 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1W H1W 0.92(3)
N1 C7 1.362(3)
N1 C6 1.409(3)
N1 H1A 0.88(3)
O1 C7 1.215(2)
F1 C3 1.360(3)
C1 C2 1.384(3)
C1 C6 1.389(3)
C1 H1B 0.9300
F2 C5 1.354(3)
O2 C10 1.344(3)
O2 N2 1.406(3)
N2 C9 1.299(3)
C2 C3 1.355(4)
C2 H2B 0.9300
C3 C4 1.368(4)
C4 C5 1.363(3)
C4 H4A 0.9300
C5 C6 1.387(3)
C7 C8 1.478(3)
C8 C10 1.363(3)
C8 C9 1.404(3)
C9 H9A 0.9300
C10 C11 1.475(3)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C11 H11D 0.9600
C11 H11E 0.9600
C11 H11F 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A O1W . 0.88(3) 2.26(3) 3.052(3) 150(2)
O1W H1W N2 6_565 0.92(3) 2.03(3) 2.934(2) 167(3)
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
C10 O2 N2 C9 1.0(3)
C6 C1 C2 C3 -0.2(4)
C1 C2 C3 F1 -179.4(3)
C1 C2 C3 C4 0.3(5)
C2 C3 C4 C5 0.6(4)
F1 C3 C4 C5 -179.7(3)
C3 C4 C5 F2 178.2(2)
C3 C4 C5 C6 -1.6(4)
F2 C5 C6 C1 -178.2(2)
C4 C5 C6 C1 1.6(4)
F2 C5 C6 N1 1.3(3)
C4 C5 C6 N1 -178.9(2)
C2 C1 C6 C5 -0.7(4)
C2 C1 C6 N1 179.9(2)
C7 N1 C6 C5 -169.5(2)
C7 N1 C6 C1 9.9(4)
C6 N1 C7 O1 -3.4(4)
C6 N1 C7 C8 176.0(2)
O1 C7 C8 C10 -13.8(3)
N1 C7 C8 C10 166.8(2)
O1 C7 C8 C9 162.3(2)
N1 C7 C8 C9 -17.1(3)
O2 N2 C9 C8 -0.6(3)
C10 C8 C9 N2 0.0(3)
C7 C8 C9 N2 -176.8(2)
N2 O2 C10 C8 -1.0(3)
N2 O2 C10 C11 178.9(2)
C9 C8 C10 O2 0.6(2)
C7 C8 C10 O2 177.6(2)
C9 C8 C10 C11 -179.2(3)
C7 C8 C10 C11 -2.2(4)
