#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/41/2214131.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_2214131
loop_
_publ_author_name
'Xin-Hong Chang'
_publ_section_title
;
 3-(2-Chlorophenyl)-N-methylisoxazole-5-carboxamide
;
_journal_coeditor_code           CV2248
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3074
_journal_page_last               o3074
_journal_paper_doi               10.1107/S1600536807025895
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C11 H9 Cl N2 O2'
_chemical_formula_moiety         'C11 H9 Cl N2 O2'
_chemical_formula_sum            'C11 H9 Cl N2 O2'
_chemical_formula_weight         236.65
_chemical_name_systematic
;
3-(2-Chlorophenyl)-N-methylisoxazole-5-carboxamide
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   18.722(4)
_cell_length_b                   31.454(6)
_cell_length_c                   7.2137(14)
_cell_measurement_reflns_used    622
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.258
_cell_measurement_theta_min      2.704
_cell_volume                     4248.0(15)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2001)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5233
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.53
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_T_max  0.8774
_exptl_absorpt_correction_T_min  0.8439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.146
_refine_ls_abs_structure_details 'Flack (1983), with 737 Friedel pairs'
_refine_ls_abs_structure_Flack   0.05(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1630
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0315
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0452P)²+3.3758P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0821
_reflns_number_gt                1563
_reflns_number_total             1630
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2248.cif
_cod_data_source_block           I
_cod_original_cell_volume        4248.1(14)
_cod_database_code               2214131
_cod_database_fobs_code          2214131
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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
Cl Cl1 0.40451(3) 0.01932(2) 0.63140(14) 0.0677(3) Uani d . 1
O O1 0.15158(7) 0.05205(5) 0.7033(3) 0.0466(4) Uani d . 1
C C4 0.28830(11) -0.02604(7) 0.7458(3) 0.0365(5) Uani d . 1
C C10 0.18338(12) 0.12278(7) 0.7981(3) 0.0397(5) Uani d . 1
O O2 0.12321(9) 0.13506(6) 0.7591(3) 0.0578(5) Uani d . 1
N N2 0.23485(9) 0.14753(6) 0.8611(3) 0.0445(5) Uani d . 1
H H2A 0.2762 0.1366 0.8827 0.053 Uiso calc R 1
N N1 0.17918(10) 0.01105(6) 0.6847(3) 0.0452(5) Uani d . 1
C C7 0.24522(12) 0.01304(7) 0.7449(3) 0.0349(5) Uani d . 1
C C8 0.26279(11) 0.05475(7) 0.8031(3) 0.0367(5) Uani d . 1
H H8A 0.3061 0.0643 0.8506 0.044 Uiso calc R 1
C C9 0.20348(11) 0.07743(7) 0.7747(3) 0.0362(5) Uani d . 1
C C5 0.36072(12) -0.02668(8) 0.7037(4) 0.0428(6) Uani d . 1
C C6 0.39989(14) -0.06374(9) 0.7098(4) 0.0579(8) Uani d . 1
H H6A 0.4482 -0.0633 0.6804 0.070 Uiso calc R 1
C C3 0.25671(14) -0.06454(8) 0.7907(4) 0.0462(6) Uani d . 1
H H3A 0.2081 -0.0653 0.8169 0.055 Uiso calc R 1
C C2 0.29559(15) -0.10164(9) 0.7974(4) 0.0570(7) Uani d . 1
H H2B 0.2731 -0.1271 0.8278 0.068 Uiso calc R 1
C C11 0.22384(14) 0.19281(8) 0.8955(5) 0.0608(8) Uani d . 1
H H11A 0.2622 0.2036 0.9702 0.091 Uiso calc R 1
H H11B 0.1794 0.1969 0.9593 0.091 Uiso calc R 1
H H11C 0.2227 0.2078 0.7795 0.091 Uiso calc R 1
C C1 0.36764(16) -0.10126(9) 0.7592(5) 0.0611(8) Uani d . 1
H H1B 0.3942 -0.1262 0.7669 0.073 Uiso calc R 1
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'
Cl Cl 0.1484 0.1585 '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
C9 O1 N1 108.32(16)
C3 C4 C5 117.0(2)
C3 C4 C7 119.8(2)
C5 C4 C7 123.1(2)
O2 C10 N2 124.4(2)
O2 C10 C9 120.7(2)
N2 C10 C9 114.88(19)
C10 N2 C11 122.0(2)
C10 N2 H2A 119.0
C11 N2 H2A 119.0
C7 N1 O1 105.85(18)
N1 C7 C8 111.17(19)
N1 C7 C4 118.6(2)
C8 C7 C4 130.2(2)
C9 C8 C7 104.85(19)
C9 C8 H8A 127.6
C7 C8 H8A 127.6
C8 C9 O1 109.8(2)
C8 C9 C10 134.9(2)
O1 C9 C10 115.23(18)
C6 C5 C4 121.7(2)
C6 C5 Cl1 117.47(19)
C4 C5 Cl1 120.82(17)
C1 C6 C5 120.1(2)
C1 C6 H6A 120.0
C5 C6 H6A 120.0
C2 C3 C4 121.6(2)
C2 C3 H3A 119.2
C4 C3 H3A 119.2
C3 C2 C1 120.3(3)
C3 C2 H2B 119.9
C1 C2 H2B 119.9
N2 C11 H11A 109.5
N2 C11 H11B 109.5
H11A C11 H11B 109.5
N2 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C6 C1 C2 119.4(2)
C6 C1 H1B 120.3
C2 C1 H1B 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C5 1.743(3)
O1 C9 1.359(3)
O1 N1 1.396(3)
C4 C3 1.386(3)
C4 C5 1.390(3)
C4 C7 1.470(3)
C10 O2 1.224(3)
C10 N2 1.320(3)
C10 C9 1.485(3)
N2 C11 1.460(3)
N2 H2A 0.8600
N1 C7 1.312(3)
C7 C8 1.416(3)
C8 C9 1.336(3)
C8 H8A 0.9300
C5 C6 1.378(3)
C6 C1 1.373(4)
C6 H6A 0.9300
C3 C2 1.376(4)
C3 H3A 0.9300
C2 C1 1.377(4)
C2 H2B 0.9300
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C1 H1B 0.9300
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
_geom_hbond_publ_flag
N2 H2A O2 3 0.86 2.14 2.983(3) 164.9 yes
C8 H8A O2 3 0.93 2.33 3.173(3) 150.6 yes
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
O2 C10 N2 C11 1.6(5)
C9 C10 N2 C11 -178.9(2)
C9 O1 N1 C7 0.2(2)
O1 N1 C7 C8 -0.3(3)
O1 N1 C7 C4 178.9(2)
C3 C4 C7 N1 -37.5(3)
C5 C4 C7 N1 142.7(2)
C3 C4 C7 C8 141.5(2)
C5 C4 C7 C8 -38.4(4)
N1 C7 C8 C9 0.2(3)
C4 C7 C8 C9 -178.8(2)
C7 C8 C9 O1 0.0(3)
C7 C8 C9 C10 -178.0(3)
N1 O1 C9 C8 -0.1(3)
N1 O1 C9 C10 178.25(19)
O2 C10 C9 C8 179.7(3)
N2 C10 C9 C8 0.2(4)
O2 C10 C9 O1 1.9(3)
N2 C10 C9 O1 -177.7(2)
C3 C4 C5 C6 -1.3(4)
C7 C4 C5 C6 178.6(2)
C3 C4 C5 Cl1 175.96(18)
C7 C4 C5 Cl1 -4.2(3)
C4 C5 C6 C1 -0.3(4)
Cl1 C5 C6 C1 -177.7(2)
C5 C4 C3 C2 1.4(4)
C7 C4 C3 C2 -178.4(2)
C4 C3 C2 C1 0.0(4)
C5 C6 C1 C2 1.8(5)
C3 C2 C1 C6 -1.7(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21124241
