#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/94/2239424.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_2239424
loop_
_publ_author_name
'Boulebd, Houssem'
'Bouraiou, Abdelmalek'
'Bouacida, Sofiane'
'Merazig, Hocine'
'Belfaitah, Ali'
_publ_section_title
;
 3-Anilino-5,5-dimethylcyclohex-2-enone
;
_journal_coeditor_code           BQ2392
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o233
_journal_page_last               o234
_journal_paper_doi               10.1107/S160053681400186X
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C14 H17 N O'
_chemical_formula_moiety         'C14 H17 N O'
_chemical_formula_sum            'C14 H17 N O'
_chemical_formula_weight         215.29
_chemical_name_systematic
;
3-Anilino-5,5-dimethylcyclohex-2-enone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.062(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1766(19)
_cell_length_b                   13.159(2)
_cell_length_c                   9.2877(17)
_cell_measurement_reflns_used    4703
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      34.27
_cell_measurement_theta_min      2.58
_cell_volume                     1206.5(4)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001)'
_computing_publication_material
;
WinGX (Farrugia, 2012) and CRYSCAL (T. Roisnel, local program)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2002 (Burla et al., 2005)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12403
_diffrn_reflns_theta_full        34.32
_diffrn_reflns_theta_max         34.32
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_correction_T_min  0.6674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2002)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.199
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         5021
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.063
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0725P)²+0.1791P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1384
_reflns_number_gt                3873
_reflns_number_total             5021
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bq2392sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239424
_cod_database_fobs_code          2239424
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C C1 0.64385(8) 0.73838(6) 0.82567(9) 0.01988(15) Uani d . 1 1
C C2 0.53143(8) 0.78529(6) 0.72449(9) 0.01973(15) Uani d . 1 1
H H2 0.4742 0.7455 0.6531 0.024 Uiso calc R 1 1
C C3 0.50602(8) 0.88768(6) 0.73022(9) 0.01767(14) Uani d . 1 1
C C4 0.59803(8) 0.95491(6) 0.84239(10) 0.02194(16) Uani d . 1 1
H H4A 0.5593 0.963 0.9274 0.026 Uiso calc R 1 1
H H4B 0.6012 1.0216 0.7987 0.026 Uiso calc R 1 1
C C5 0.74309(8) 0.91494(6) 0.89647(9) 0.01943(15) Uani d . 1 1
C C6 0.73478(9) 0.80376(6) 0.94261(9) 0.02232(16) Uani d . 1 1
H H6A 0.8253 0.775 0.9661 0.027 Uiso calc R 1 1
H H6B 0.7019 0.8017 1.0322 0.027 Uiso calc R 1 1
C C7 0.81684(10) 0.97776(8) 1.03068(11) 0.0320(2) Uani d . 1 1
H H7A 0.7703 0.9715 1.1086 0.048 Uiso calc R 1 1
H H7B 0.8185 1.0478 1.0024 0.048 Uiso calc R 1 1
H H7C 0.908 0.9533 1.0652 0.048 Uiso calc R 1 1
C C8 0.81959(9) 0.92285(7) 0.77337(10) 0.02490(17) Uani d . 1 1
H H8A 0.8268 0.9929 0.7477 0.037 Uiso calc R 1 1
H H8B 0.7712 0.886 0.6876 0.037 Uiso calc R 1 1
H H8C 0.9086 0.8945 0.8079 0.037 Uiso calc R 1 1
C C10 0.29024(8) 0.89121(6) 0.53767(9) 0.01887(15) Uani d . 1 1
C C11 0.15721(8) 0.90959(7) 0.54586(10) 0.02316(16) Uani d . 1 1
H H11 0.1403 0.95 0.6215 0.028 Uiso calc R 1 1
C C12 0.04984(9) 0.86746(7) 0.44081(12) 0.0306(2) Uani d . 1 1
H H12 -0.0388 0.88 0.4461 0.037 Uiso calc R 1 1
C C13 0.07470(11) 0.80686(7) 0.32830(13) 0.0351(2) Uani d . 1 1
H H13 0.003 0.7781 0.2587 0.042 Uiso calc R 1 1
C C14 0.20729(11) 0.78931(8) 0.31997(12) 0.0343(2) Uani d . 1 1
H H14 0.2239 0.7488 0.2443 0.041 Uiso calc R 1 1
C C15 0.31524(9) 0.83168(7) 0.42365(10) 0.02586(18) Uani d . 1 1
H H15 0.4037 0.8203 0.4168 0.031 Uiso calc R 1 1
N N1 0.39813(7) 0.93664(5) 0.64459(8) 0.02126(14) Uani d . 1 1
H H1 0.3945 1.0014 0.6559 0.026 Uiso calc R 1 1
O O1 0.66676(7) 0.64544(5) 0.82303(9) 0.03086(17) Uani d . 1 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 0 '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 0.006 '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
O1 C1 C2 122.25(8)
O1 C1 C6 119.18(7)
C2 C1 C6 118.54(7)
C3 C2 C1 121.65(7)
C3 C2 H2 119.2
C1 C2 H2 119.2
N1 C3 C2 125.26(7)
N1 C3 C4 113.97(7)
C2 C3 C4 120.72(7)
C3 C4 C5 114.36(7)
C3 C4 H4A 108.7
C5 C4 H4A 108.7
C3 C4 H4B 108.7
C5 C4 H4B 108.7
H4A C4 H4B 107.6
C7 C5 C4 108.91(7)
C7 C5 C6 109.70(7)
C4 C5 C6 107.77(7)
C7 C5 C8 109.43(7)
C4 C5 C8 110.80(7)
C6 C5 C8 110.20(7)
C1 C6 C5 114.07(7)
C1 C6 H6A 108.7
C5 C6 H6A 108.7
C1 C6 H6B 108.7
C5 C6 H6B 108.7
H6A C6 H6B 107.6
C5 C7 H7A 109.5
C5 C7 H7B 109.5
H7A C7 H7B 109.5
C5 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C5 C8 H8A 109.5
C5 C8 H8B 109.5
H8A C8 H8B 109.5
C5 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C15 C10 C11 119.93(8)
C15 C10 N1 121.09(7)
C11 C10 N1 118.95(8)
C12 C11 C10 119.99(9)
C12 C11 H11 120
C10 C11 H11 120
C13 C12 C11 120.13(9)
C13 C12 H12 119.9
C11 C12 H12 119.9
C12 C13 C14 119.69(9)
C12 C13 H13 120.2
C14 C13 H13 120.2
C13 C14 C15 120.64(10)
C13 C14 H14 119.7
C15 C14 H14 119.7
C10 C15 C14 119.61(9)
C10 C15 H15 120.2
C14 C15 H15 120.2
C3 N1 C10 126.13(7)
C3 N1 H1 116.9
C10 N1 H1 116.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2463(10)
C1 C2 1.4320(11)
C1 C6 1.5126(12)
C2 C3 1.3754(11)
C2 H2 0.93
C3 N1 1.3523(10)
C3 C4 1.5069(11)
C4 C5 1.5323(12)
C4 H4A 0.97
C4 H4B 0.97
C5 C7 1.5316(12)
C5 C6 1.5326(12)
C5 C8 1.5351(12)
C6 H6A 0.97
C6 H6B 0.97
C7 H7A 0.96
C7 H7B 0.96
C7 H7C 0.96
C8 H8A 0.96
C8 H8B 0.96
C8 H8C 0.96
C10 C15 1.3895(12)
C10 C11 1.3954(12)
C10 N1 1.4209(10)
C11 C12 1.3911(13)
C11 H11 0.93
C12 C13 1.3857(16)
C12 H12 0.93
C13 C14 1.3895(16)
C13 H13 0.93
C14 C15 1.3896(13)
C14 H14 0.93
C15 H15 0.93
N1 H1 0.86
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
N1 H1 O1 2_656 0.8600 2.0200 2.8587(11) 165.00 yes
C8 H8A Cg1 3_676 0.96 2.61 3.5547(12) 157 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
O1 C1 C2 C3 178.90(8)
C6 C1 C2 C3 0.93(12)
C1 C2 C3 N1 -176.05(8)
C1 C2 C3 C4 1.17(12)
N1 C3 C4 C5 -157.43(7)
C2 C3 C4 C5 25.06(11)
C3 C4 C5 C7 -168.72(7)
C3 C4 C5 C6 -49.78(9)
C3 C4 C5 C8 70.86(9)
O1 C1 C6 C5 152.80(8)
C2 C1 C6 C5 -29.16(11)
C7 C5 C6 C1 170.28(7)
C4 C5 C6 C1 51.84(9)
C8 C5 C6 C1 -69.18(9)
C15 C10 C11 C12 0.66(12)
N1 C10 C11 C12 178.82(7)
C10 C11 C12 C13 0.27(13)
C11 C12 C13 C14 -0.70(15)
C12 C13 C14 C15 0.19(16)
C11 C10 C15 C14 -1.17(13)
N1 C10 C15 C14 -179.28(8)
C13 C14 C15 C10 0.74(15)
C2 C3 N1 C10 2.19(14)
C4 C3 N1 C10 -175.20(7)
C15 C10 N1 C3 -54.91(12)
C11 C10 N1 C3 126.96(9)
