#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/44/2224458.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_2224458
loop_
_publ_author_name
'Cheng, Qingfang'
'Wang, Qi-fa'
'Liu, Li-sha'
'Zhang, Jun-lei'
_publ_section_title
(Z)-4-[4-(Dimethylamino)benzylidene]-3-methylisoxazol-5(4H)-one
_journal_coeditor_code           SU2156
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3074
_journal_paper_doi               10.1107/S160053680904714X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H14 N2 O2'
_chemical_formula_moiety         'C13 H14 N2 O2'
_chemical_formula_sum            'C13 H14 N2 O2'
_chemical_formula_weight         230.26
_chemical_name_systematic
;
(Z)-4-[4-(Dimethylamino)benzylidene]-3-methylisoxazol-5(4H)-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.272(2)
_cell_angle_beta                 97.3190(10)
_cell_angle_gamma                101.461(2)
_cell_formula_units_Z            2
_cell_length_a                   6.4201(10)
_cell_length_b                   7.8239(12)
_cell_length_c                   12.1901(15)
_cell_measurement_reflns_used    607
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.089
_cell_measurement_theta_min      2.897
_cell_volume                     582.01(15)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0794
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2990
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.90
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9928
_exptl_absorpt_correction_T_min  0.9884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.289
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2020
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1434
_refine_ls_R_factor_gt           0.0692
_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)+(0.069P)²+] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1503
_refine_ls_wR_factor_ref         0.1777
_reflns_number_gt                943
_reflns_number_total             2020
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2156.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2224458
_cod_database_fobs_code          2224458
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.7351(5) 0.6599(4) 0.8929(3) 0.0671(10) Uani d . 1 . .
N N2 0.3808(5) 0.8488(4) 0.1943(3) 0.0604(9) Uani d . 1 . .
O O1 0.9130(4) 0.7385(4) 0.8421(2) 0.0746(9) Uani d . 1 . .
O O2 0.9643(4) 0.8104(4) 0.6764(2) 0.0797(9) Uani d . 1 . .
C C1 0.8347(6) 0.7524(5) 0.7333(4) 0.0626(11) Uani d . 1 . .
C C2 0.6035(5) 0.6855(5) 0.7140(3) 0.0492(9) Uani d . 1 . .
C C3 0.5624(5) 0.6321(4) 0.8187(3) 0.0503(9) Uani d . 1 . .
C C4 0.3517(5) 0.5490(5) 0.8451(3) 0.0634(11) Uani d . 1 . .
H H4A 0.3722 0.5237 0.9195 0.095 Uiso calc R 1 . .
H H4B 0.2895 0.4400 0.7907 0.095 Uiso calc R 1 . .
H H4C 0.2568 0.6293 0.8423 0.095 Uiso calc R 1 . .
C C5 0.4464(5) 0.6758(4) 0.6248(3) 0.0506(9) Uani d . 1 . .
H H5 0.3094 0.6266 0.6373 0.061 Uiso calc R 1 . .
C C6 0.4428(5) 0.7234(4) 0.5171(3) 0.0458(9) Uani d . 1 . .
C C7 0.2412(5) 0.6921(5) 0.4469(3) 0.0546(10) Uani d . 1 . .
H H7 0.1181 0.6420 0.4730 0.066 Uiso calc R 1 . .
C C8 0.2192(5) 0.7323(5) 0.3417(3) 0.0563(10) Uani d . 1 . .
H H8 0.0829 0.7086 0.2980 0.068 Uiso calc R 1 . .
C C9 0.4013(5) 0.8091(4) 0.2993(3) 0.0496(9) Uani d . 1 . .
C C10 0.6035(5) 0.8435(5) 0.3700(3) 0.0526(10) Uani d . 1 . .
H H10 0.7264 0.8965 0.3448 0.063 Uiso calc R 1 . .
C C11 0.6244(5) 0.8012(4) 0.4750(3) 0.0507(9) Uani d . 1 . .
H H11 0.7605 0.8244 0.5187 0.061 Uiso calc R 1 . .
C C12 0.5668(6) 0.9262(5) 0.1481(3) 0.0691(12) Uani d . 1 . .
H H12A 0.6721 1.0058 0.2079 0.104 Uiso calc R 1 . .
H H12B 0.5224 0.9911 0.0929 0.104 Uiso calc R 1 . .
H H12C 0.6287 0.8329 0.1129 0.104 Uiso calc R 1 . .
C C13 0.1725(6) 0.8003(6) 0.1198(3) 0.0751(12) Uani d . 1 . .
H H13A 0.1191 0.6734 0.1050 0.113 Uiso calc R 1 . .
H H13B 0.1886 0.8376 0.0499 0.113 Uiso calc R 1 . .
H H13C 0.0725 0.8581 0.1555 0.113 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'
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_3
_geom_angle
_geom_angle_publ_flag
C3 N1 O1 . . 106.5(3) ?
C9 N2 C12 . . 121.9(3) ?
C9 N2 C13 . . 120.9(3) ?
C12 N2 C13 . . 117.0(3) ?
C1 O1 N1 . . 109.2(3) ?
O2 C1 O1 . . 118.0(3) ?
O2 C1 C2 . . 134.7(4) ?
O1 C1 C2 . . 107.3(3) ?
C5 C2 C1 . . 132.2(3) ?
C5 C2 C3 . . 124.2(3) ?
C1 C2 C3 . . 103.6(3) ?
N1 C3 C2 . . 113.3(3) ?
N1 C3 C4 . . 119.5(3) ?
C2 C3 C4 . . 127.1(3) ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C2 C5 C6 . . 135.0(3) ?
C2 C5 H5 . . 112.5 ?
C6 C5 H5 . . 112.5 ?
C11 C6 C7 . . 116.8(3) ?
C11 C6 C5 . . 125.4(3) ?
C7 C6 C5 . . 117.8(3) ?
C8 C7 C6 . . 122.7(3) ?
C8 C7 H7 . . 118.7 ?
C6 C7 H7 . . 118.7 ?
C7 C8 C9 . . 120.4(3) ?
C7 C8 H8 . . 119.8 ?
C9 C8 H8 . . 119.8 ?
N2 C9 C8 . . 120.8(3) ?
N2 C9 C10 . . 122.0(3) ?
C8 C9 C10 . . 117.2(3) ?
C11 C10 C9 . . 122.0(3) ?
C11 C10 H10 . . 119.0 ?
C9 C10 H10 . . 119.0 ?
C10 C11 C6 . . 120.9(3) ?
C10 C11 H11 . . 119.5 ?
C6 C11 H11 . . 119.5 ?
N2 C12 H12A . . 109.5 ?
N2 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
N2 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N2 C13 H13A . . 109.5 ?
N2 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
N2 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C3 . 1.294(4) ?
N1 O1 . 1.451(3) ?
N2 C9 . 1.367(4) ?
N2 C12 . 1.455(4) ?
N2 C13 . 1.457(4) ?
O1 C1 . 1.388(4) ?
O2 C1 . 1.220(4) ?
C1 C2 . 1.446(5) ?
C2 C5 . 1.365(5) ?
C2 C3 . 1.451(4) ?
C3 C4 . 1.481(4) ?
C4 H4A . 0.9600 ?
C4 H4B . 0.9600 ?
C4 H4C . 0.9600 ?
C5 C6 . 1.426(4) ?
C5 H5 . 0.9300 ?
C6 C11 . 1.405(4) ?
C6 C7 . 1.409(5) ?
C7 C8 . 1.371(5) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.407(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.412(5) ?
C10 C11 . 1.375(4) ?
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
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
C3 N1 O1 C1 . . . . -0.9(4) ?
N1 O1 C1 O2 . . . . -177.5(3) ?
N1 O1 C1 C2 . . . . 1.1(4) ?
O2 C1 C2 C5 . . . . -5.2(8) ?
O1 C1 C2 C5 . . . . 176.5(4) ?
O2 C1 C2 C3 . . . . 177.5(4) ?
O1 C1 C2 C3 . . . . -0.9(4) ?
O1 N1 C3 C2 . . . . 0.4(4) ?
O1 N1 C3 C4 . . . . 178.9(3) ?
C5 C2 C3 N1 . . . . -177.3(3) ?
C1 C2 C3 N1 . . . . 0.3(4) ?
C5 C2 C3 C4 . . . . 4.2(6) ?
C1 C2 C3 C4 . . . . -178.2(3) ?
C1 C2 C5 C6 . . . . 0.8(7) ?
C3 C2 C5 C6 . . . . 177.6(3) ?
C2 C5 C6 C11 . . . . -0.4(6) ?
C2 C5 C6 C7 . . . . -179.7(4) ?
C11 C6 C7 C8 . . . . 0.8(5) ?
C5 C6 C7 C8 . . . . -179.8(3) ?
C6 C7 C8 C9 . . . . -0.4(5) ?
C12 N2 C9 C8 . . . . -179.2(3) ?
C13 N2 C9 C8 . . . . -4.7(5) ?
C12 N2 C9 C10 . . . . 1.1(5) ?
C13 N2 C9 C10 . . . . 175.6(3) ?
C7 C8 C9 N2 . . . . 179.7(3) ?
C7 C8 C9 C10 . . . . -0.6(5) ?
N2 C9 C10 C11 . . . . -179.0(3) ?
C8 C9 C10 C11 . . . . 1.3(5) ?
C9 C10 C11 C6 . . . . -0.9(5) ?
C7 C6 C11 C10 . . . . -0.1(5) ?
C5 C6 C11 C10 . . . . -179.5(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4448350
