#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/68/2226871.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_2226871
loop_
_publ_author_name
'Asiri, Abdullah M.'
'Khan, Salman A.'
'Tahir, M. Nawaz'
_publ_section_title
;
 N-(4-Chlorobenzylidene)-3,4-dimethylisoxazol-5-amine
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2127
_journal_paper_doi               10.1107/S1600536810029284
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H11 Cl N2 O'
_chemical_formula_moiety         'C12 H11 Cl N2 O'
_chemical_formula_sum            'C12 H11 Cl N2 O'
_chemical_formula_weight         234.68
_chemical_name_systematic
;
N-(4-Chlorobenzylidene)-3,4-dimethylisoxazol-5-amine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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
_cell_angle_beta                 94.871(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0877(2)
_cell_length_b                   24.5197(9)
_cell_length_c                   9.4673(4)
_cell_measurement_reflns_used    1539
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      2.31
_cell_volume                     1176.77(8)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.10
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker KAPPA APEXII CCD'
_diffrn_measurement_method       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  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9016
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.31
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.144
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2112
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0435
_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)+(0.0521P)²+0.2476P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1195
_reflns_number_gt                1539
_reflns_number_total             2112
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2296.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2226871
_cod_database_fobs_code          2226871
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Cl Cl1 -0.59118(13) 0.19483(3) -0.44471(7) 0.0894(3) Uani . . 1.000
O O1 0.5343(3) 0.03641(6) 0.15781(16) 0.0736(6) Uani . . 1.000
N N1 0.3653(3) 0.11804(7) 0.05045(17) 0.0608(6) Uani . . 1.000
N N2 0.7399(4) 0.02071(8) 0.2600(2) 0.0763(7) Uani . . 1.000
C C1 -0.0022(4) 0.11701(8) -0.1255(2) 0.0576(7) Uani . . 1.000
C C2 -0.1918(4) 0.08576(9) -0.2009(2) 0.0676(8) Uani . . 1.000
C C3 -0.3750(4) 0.10921(9) -0.2987(2) 0.0701(8) Uani . . 1.000
C C4 -0.3674(4) 0.16448(9) -0.3200(2) 0.0630(8) Uani . . 1.000
C C5 -0.1824(5) 0.19639(9) -0.2446(3) 0.0775(9) Uani . . 1.000
C C6 -0.0019(4) 0.17261(10) -0.1484(3) 0.0724(8) Uani . . 1.000
C C7 0.1915(4) 0.09088(9) -0.0251(2) 0.0622(7) Uani . . 1.000
C C8 0.5459(4) 0.09160(9) 0.1431(2) 0.0576(7) Uani . . 1.000
C C9 0.7462(4) 0.11227(8) 0.2291(2) 0.0575(7) Uani . . 1.000
C C10 0.8603(4) 0.06588(9) 0.2988(2) 0.0617(7) Uani . . 1.000
C C11 1.0916(4) 0.06456(11) 0.4077(2) 0.0785(9) Uani . . 1.000
C C12 0.8318(4) 0.16992(9) 0.2438(3) 0.0778(9) Uani . . 1.000
H H2 -0.19609 0.04832 -0.18554 0.0811 Uiso . . 1.000
H H3 -0.50149 0.08784 -0.34921 0.0842 Uiso . . 1.000
H H5 -0.18016 0.23391 -0.25895 0.0930 Uiso . . 1.000
H H6 0.12298 0.19425 -0.09757 0.0869 Uiso . . 1.000
H H7 0.18824 0.05313 -0.01578 0.0746 Uiso . . 1.000
H H11A 1.15318 0.02772 0.42002 0.1177 Uiso . . 1.000
H H11B 1.03940 0.07821 0.49613 0.1177 Uiso . . 1.000
H H11C 1.23056 0.08692 0.37665 0.1177 Uiso . . 1.000
H H12A 0.72003 0.19230 0.18085 0.1168 Uiso . . 1.000
H H12B 1.01097 0.17312 0.22023 0.1168 Uiso . . 1.000
H H12C 0.81971 0.18168 0.33972 0.1168 Uiso . . 1.000
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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 O1 C8 . . . 107.69(15) no
C7 N1 C8 . . . 120.28(18) no
O1 N2 C10 . . . 105.29(17) no
C2 C1 C6 . . . 118.45(19) no
C2 C1 C7 . . . 119.77(18) no
C6 C1 C7 . . . 121.78(19) no
C1 C2 C3 . . . 121.1(2) no
C2 C3 C4 . . . 118.94(19) no
Cl1 C4 C3 . . . 119.90(16) no
Cl1 C4 C5 . . . 119.28(18) no
C3 C4 C5 . . . 120.82(19) no
C4 C5 C6 . . . 119.6(2) no
C1 C6 C5 . . . 121.1(2) no
N1 C7 C1 . . . 122.3(2) no
O1 C8 N1 . . . 120.02(18) no
O1 C8 C9 . . . 110.42(18) no
N1 C8 C9 . . . 129.6(2) no
C8 C9 C10 . . . 103.81(18) no
C8 C9 C12 . . . 128.04(19) no
C10 C9 C12 . . . 128.13(19) no
N2 C10 C9 . . . 112.79(18) no
N2 C10 C11 . . . 119.9(2) no
C9 C10 C11 . . . 127.3(2) no
C1 C2 H2 . . . 119.00 no
C3 C2 H2 . . . 119.00 no
C2 C3 H3 . . . 121.00 no
C4 C3 H3 . . . 121.00 no
C4 C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C1 C6 H6 . . . 119.00 no
C5 C6 H6 . . . 119.00 no
N1 C7 H7 . . . 119.00 no
C1 C7 H7 . . . 119.00 no
C10 C11 H11A . . . 109.00 no
C10 C11 H11B . . . 109.00 no
C10 C11 H11C . . . 109.00 no
H11A C11 H11B . . . 109.00 no
H11A C11 H11C . . . 109.00 no
H11B C11 H11C . . . 109.00 no
C9 C12 H12A . . . 109.00 no
C9 C12 H12B . . . 109.00 no
C9 C12 H12C . . . 109.00 no
H12A C12 H12B . . . 109.00 no
H12A C12 H12C . . . 109.00 no
H12B C12 H12C . . . 110.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C4 . . 1.737(2) no
O1 N2 . . 1.417(2) no
O1 C8 . . 1.362(3) no
N1 C7 . . 1.277(3) no
N1 C8 . . 1.377(3) no
N2 C10 . . 1.303(3) no
C1 C2 . . 1.382(3) no
C1 C6 . . 1.380(3) no
C1 C7 . . 1.458(3) no
C2 C3 . . 1.382(3) no
C3 C4 . . 1.371(3) no
C4 C5 . . 1.376(3) no
C5 C6 . . 1.368(4) no
C8 C9 . . 1.348(3) no
C9 C10 . . 1.415(3) no
C9 C12 . . 1.482(3) no
C10 C11 . . 1.498(3) no
C2 H2 . . 0.9300 no
C3 H3 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
C7 H7 . . 0.9300 no
C11 H11A . . 0.9600 no
C11 H11B . . 0.9600 no
C11 H11C . . 0.9600 no
C12 H12A . . 0.9600 no
C12 H12B . . 0.9600 no
C12 H12C . . 0.9600 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl1 H12C 3.0600 . 1_454 no
O1 H7 2.3400 . . no
O1 H2 2.7200 . 3_555 no
N1 H6 2.5800 . . no
N1 H12A 2.7800 . . no
N1 H12B 2.8500 . 1_455 no
C3 C7 3.570(3) . 1_455 no
C7 C3 3.570(3) . 1_655 no
C7 C9 3.482(3) . 1_455 no
C9 C7 3.482(3) . 1_655 no
C3 H11B 3.0800 . 1_454 no
C8 H11C 2.8400 . 1_455 no
C11 H3 3.0200 . 1_756 no
C12 H11C 3.0700 . . no
H2 H7 2.4300 . . no
H2 O1 2.7200 . 3_555 no
H3 C11 3.0200 . 1_354 no
H6 N1 2.5800 . . no
H7 O1 2.3400 . . no
H7 H2 2.4300 . . no
H11B C3 3.0800 . 1_656 no
H11C C8 2.8400 . 1_655 no
H11C C12 3.0700 . . no
H12A N1 2.7800 . . no
H12B N1 2.8500 . 1_655 no
H12C Cl1 3.0600 . 1_656 no
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
C7 H7 O1 . 0.93 2.34 2.704(3) 103 yes
C11 H11C Cg1 1_655 0.96 2.91 3.644(2) 134 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 O1 N2 C10 . . . . -0.4(2) no
N2 O1 C8 N1 . . . . -179.39(17) no
N2 O1 C8 C9 . . . . 0.1(2) no
C8 N1 C7 C1 . . . . -179.45(18) no
C7 N1 C8 O1 . . . . -2.1(3) no
C7 N1 C8 C9 . . . . 178.5(2) no
O1 N2 C10 C9 . . . . 0.5(2) no
O1 N2 C10 C11 . . . . 179.91(17) no
C6 C1 C2 C3 . . . . 1.0(3) no
C7 C1 C2 C3 . . . . -178.80(18) no
C2 C1 C6 C5 . . . . -0.8(3) no
C7 C1 C6 C5 . . . . 179.0(2) no
C2 C1 C7 N1 . . . . -177.71(19) no
C6 C1 C7 N1 . . . . 2.5(3) no
C1 C2 C3 C4 . . . . -0.3(3) no
C2 C3 C4 Cl1 . . . . 178.75(15) no
C2 C3 C4 C5 . . . . -0.6(3) no
Cl1 C4 C5 C6 . . . . -178.59(19) no
C3 C4 C5 C6 . . . . 0.8(4) no
C4 C5 C6 C1 . . . . 0.0(4) no
O1 C8 C9 C10 . . . . 0.2(2) no
O1 C8 C9 C12 . . . . 178.5(2) no
N1 C8 C9 C10 . . . . 179.6(2) no
N1 C8 C9 C12 . . . . -2.1(4) no
C8 C9 C10 N2 . . . . -0.4(2) no
C8 C9 C10 C11 . . . . -179.78(19) no
C12 C9 C10 N2 . . . . -178.7(2) no
C12 C9 C10 C11 . . . . 1.9(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745637
