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#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/85/2228553.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228553
loop_
_publ_author_name
'Soydemir, Erkan'
'Büyükgüngör, Orhan'
'Albayrak, Çiğdem'
_publ_section_title
;
 3-Diethylamino-6-[(Z)-(4-hydroxyanilino)methylidene]cyclohexa-2,4-dienone
;
_journal_coeditor_code           SI2307
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3138
_journal_page_last               o3139
_journal_paper_doi               10.1107/S1600536810045939
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H20 N2 O2'
_chemical_formula_moiety         'C17 H20 N2 O2'
_chemical_formula_sum            'C17 H20 N2 O2'
_chemical_formula_weight         284.35
_chemical_name_systematic
;
3-Diethylamino-6-[(Z)-(4-hydroxyanilino)methylidene]cyclohexa-2,4-
dienone
;
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.400(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2648(4)
_cell_length_b                   11.8968(4)
_cell_length_c                   16.6149(7)
_cell_measurement_reflns_used    18967
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.01
_cell_measurement_theta_min      1.71
_cell_volume                     1510.39(11)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'rotation method'
_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  0.0672
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18967
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.17
_diffrn_standards_decay_%        0.1
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9788
_exptl_absorpt_correction_T_min  0.9567
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.271
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3143
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0651
_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)+(0.0969P)²+0.3716P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1745
_refine_ls_wR_factor_ref         0.1885
_reflns_number_gt                2416
_reflns_number_total             3143
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            si2307.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228553
_cod_database_fobs_code          2228553
loop_
_symmetry_equiv_pos_as_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_disorder_assembly
_atom_site_disorder_group
C C1 0.8028(2) 0.31443(16) 0.65717(13) 0.0483(5) Uani d . 1 . .
C C2 0.9660(3) 0.35845(19) 0.70654(14) 0.0549(5) Uani d . 1 . .
H H3 1.0126 0.4163 0.6844 0.066 Uiso calc R 1 . .
C C3 1.0587(3) 0.31624(19) 0.78840(14) 0.0581(5) Uani d . 1 . .
H H2 1.1680 0.3463 0.8212 0.070 Uiso calc R 1 . .
C C4 0.9927(3) 0.22989(19) 0.82301(13) 0.0550(5) Uani d . 1 . .
C C5 0.8278(3) 0.1876(2) 0.77383(16) 0.0627(6) Uani d . 1 . .
H H6 0.7800 0.1309 0.7963 0.075 Uiso calc R 1 . .
C C6 0.7352(3) 0.22939(19) 0.69203(15) 0.0593(6) Uani d . 1 . .
H H5 0.6253 0.2001 0.6595 0.071 Uiso calc R 1 . .
C C7 0.7361(2) 0.42738(17) 0.52483(13) 0.0501(5) Uani d . 1 . .
H H7 0.8386 0.4689 0.5495 0.060 Uiso calc R 1 . .
C C8 0.6253(2) 0.44989(16) 0.43902(12) 0.0470(5) Uani d . 1 . .
C C9 0.6675(3) 0.53469(18) 0.39085(14) 0.0536(5) Uani d . 1 . .
H H9 0.7688 0.5766 0.4180 0.064 Uiso calc R 1 . .
C C10 0.5666(3) 0.55735(19) 0.30686(14) 0.0567(5) Uani d . 1 . .
H H10 0.6000 0.6134 0.2774 0.068 Uiso calc R 1 . .
C C11 0.4090(3) 0.49573(19) 0.26311(13) 0.0556(5) Uani d . 1 . .
C C12 0.3648(3) 0.41193(19) 0.30976(13) 0.0552(5) Uani d . 1 . .
H H12 0.2638 0.3701 0.2816 0.066 Uiso calc R 1 . .
C C13 0.4654(2) 0.38791(17) 0.39687(12) 0.0473(5) Uani d . 1 . .
C C14 0.1382(4) 0.4570(2) 0.13497(16) 0.0802(8) Uani d U 1 . .
H H15A 0.0600 0.5023 0.0875 0.096 Uiso calc R 1 . .
H H15B 0.0819 0.4447 0.1759 0.096 Uiso calc R 1 . .
C C15 0.3476(4) 0.6042(3) 0.12686(17) 0.0855(8) Uani d . 1 . .
H H14A 0.4063 0.6671 0.1634 0.103 Uiso calc R 1 A 1
H H14B 0.2416 0.6319 0.0815 0.103 Uiso calc R 1 A 1
C C16A 0.4682(17) 0.5521(6) 0.0854(7) 0.096(3) Uani d PU 0.59(2) B 1
H H16A 0.4960 0.6078 0.0508 0.144 Uiso calc PR 0.59(2) B 1
H H16B 0.4097 0.4900 0.0491 0.144 Uiso calc PR 0.59(2) B 1
H H16C 0.5741 0.5262 0.1304 0.144 Uiso calc PR 0.59(2) B 1
C C16B 0.388(3) 0.5630(9) 0.0567(10) 0.097(4) Uani d PU 0.41(2) B 2
H H16D 0.4141 0.6249 0.0267 0.145 Uiso calc PR 0.41(2) B 2
H H16E 0.2888 0.5224 0.0171 0.145 Uiso calc PR 0.41(2) B 2
H H16F 0.4868 0.5137 0.0785 0.145 Uiso calc PR 0.41(2) B 2
C C17 0.1651(5) 0.3472(3) 0.1001(2) 0.1033(11) Uani d . 1 . .
H H17A 0.0543 0.3102 0.0725 0.155 Uiso calc R 1 . .
H H17B 0.2406 0.3013 0.1468 0.155 Uiso calc R 1 . .
H H17C 0.2177 0.3588 0.0583 0.155 Uiso calc R 1 . .
N N1 0.7013(2) 0.35026(14) 0.57193(11) 0.0500(4) Uani d . 1 . .
H H1B 0.597(3) 0.316(2) 0.5437(17) 0.066(7) Uiso d . 1 . .
N N2 0.3028(3) 0.51988(19) 0.17918(12) 0.0712(6) Uani d U 1 B .
O O1 1.0820(2) 0.18478(17) 0.90278(11) 0.0723(5) Uani d . 1 . .
H H1A 1.193(5) 0.197(3) 0.919(3) 0.131(14) Uiso d . 1 . .
O O2 0.41712(18) 0.31201(13) 0.43958(9) 0.0573(4) Uani d . 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
C6 C1 C2 . . 119.00(19) ?
C6 C1 N1 . . 117.45(17) ?
C2 C1 N1 . . 123.54(19) ?
C3 C2 C1 . . 119.8(2) ?
C3 C2 H3 . . 120.1 ?
C1 C2 H3 . . 120.1 ?
C2 C3 C4 . . 121.39(19) ?
C2 C3 H2 . . 119.3 ?
C4 C3 H2 . . 119.3 ?
O1 C4 C3 . . 123.0(2) ?
O1 C4 C5 . . 118.5(2) ?
C3 C4 C5 . . 118.50(19) ?
C6 C5 C4 . . 120.2(2) ?
C6 C5 H6 . . 119.9 ?
C4 C5 H6 . . 119.9 ?
C5 C6 C1 . . 121.10(19) ?
C5 C6 H5 . . 119.4 ?
C1 C6 H5 . . 119.4 ?
N1 C7 C8 . . 122.57(18) ?
N1 C7 H7 . . 118.7 ?
C8 C7 H7 . . 118.7 ?
C7 C8 C9 . . 120.58(18) ?
C7 C8 C13 . . 121.43(18) ?
C9 C8 C13 . . 118.00(17) ?
C10 C9 C8 . . 122.60(19) ?
C10 C9 H9 . . 118.7 ?
C8 C9 H9 . . 118.7 ?
C9 C10 C11 . . 120.5(2) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
N2 C11 C12 . . 121.0(2) ?
N2 C11 C10 . . 121.2(2) ?
C12 C11 C10 . . 117.73(19) ?
C11 C12 C13 . . 122.95(19) ?
C11 C12 H12 . . 118.5 ?
C13 C12 H12 . . 118.5 ?
O2 C13 C12 . . 121.47(18) ?
O2 C13 C8 . . 120.34(17) ?
C12 C13 C8 . . 118.20(19) ?
N2 C14 C17 . . 113.2(3) ?
N2 C14 H15A . . 108.9 ?
C17 C14 H15A . . 108.9 ?
N2 C14 H15B . . 108.9 ?
C17 C14 H15B . . 108.9 ?
H15A C14 H15B . . 107.8 ?
C16B C15 N2 . . 116.3(5) ?
N2 C15 C16A . . 110.1(4) ?
C16B C15 H14A . . 124.5 ?
N2 C15 H14A . . 109.6 ?
C16A C15 H14A . . 109.6 ?
C16B C15 H14B . . 84.4 ?
N2 C15 H14B . . 109.6 ?
C16A C15 H14B . . 109.6 ?
H14A C15 H14B . . 108.2 ?
C15 C16A H16A . . 109.5 ?
C15 C16A H16B . . 109.5 ?
H16A C16A H16B . . 109.5 ?
C15 C16A H16C . . 109.5 ?
H16A C16A H16C . . 109.5 ?
H16B C16A H16C . . 109.5 ?
C15 C16B H16D . . 109.5 ?
C15 C16B H16E . . 109.5 ?
H16D C16B H16E . . 109.5 ?
C15 C16B H16F . . 109.5 ?
H16D C16B H16F . . 109.5 ?
H16E C16B H16F . . 109.5 ?
C14 C17 H17A . . 109.5 ?
C14 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C14 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C7 N1 C1 . . 129.19(18) ?
C7 N1 H1B . . 112.7(16) ?
C1 N1 H1B . . 118.1(16) ?
C11 N2 C15 . . 122.7(2) ?
C11 N2 C14 . . 120.8(2) ?
C15 N2 C14 . . 116.4(2) ?
C4 O1 H1A . . 111(3) ?
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
C1 C6 . 1.385(3) ?
C1 C2 . 1.387(3) ?
C1 N1 . 1.409(3) ?
C2 C3 . 1.377(3) ?
C2 H3 . 0.9300 ?
C3 C4 . 1.387(3) ?
C3 H2 . 0.9300 ?
C4 O1 . 1.358(3) ?
C4 C5 . 1.389(3) ?
C5 C6 . 1.374(3) ?
C5 H6 . 0.9300 ?
C6 H5 . 0.9300 ?
C7 N1 . 1.307(3) ?
C7 C8 . 1.396(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.412(3) ?
C8 C13 . 1.441(3) ?
C9 C10 . 1.352(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.429(3) ?
C10 H10 . 0.9300 ?
C11 N2 . 1.366(3) ?
C11 C12 . 1.394(3) ?
C12 C13 . 1.397(3) ?
C12 H12 . 0.9300 ?
C13 O2 . 1.301(2) ?
C14 N2 . 1.479(3) ?
C14 C17 . 1.481(4) ?
C14 H15A . 0.9700 ?
C14 H15B . 0.9700 ?
C15 C16B . 1.415(9) ?
C15 N2 . 1.465(3) ?
C15 C16A . 1.541(8) ?
C15 H14A . 0.9700 ?
C15 H14B . 0.9700 ?
C16A H16A . 0.9600 ?
C16A H16B . 0.9600 ?
C16A H16C . 0.9600 ?
C16B H16D . 0.9600 ?
C16B H16E . 0.9600 ?
C16B H16F . 0.9600 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
N1 H1B . 0.90(3) ?
O1 H1A . 0.87(4) ?
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 H1B O2 . 0.90(3) 1.80(3) 2.574(2) 142(2)
O1 H1A O2 4_666 0.87(4) 1.75(4) 2.599(2) 165(4)
C16A H16A O2 2_655 0.96 2.52 3.306(7) 138.9
C5 H6 Cg1 4_555 0.93 2.93 3.799(3) 156
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
C6 C1 C2 C3 . . . . 0.9(3) ?
N1 C1 C2 C3 . . . . -178.06(19) ?
C1 C2 C3 C4 . . . . 0.1(3) ?
C2 C3 C4 O1 . . . . 178.7(2) ?
C2 C3 C4 C5 . . . . -1.3(3) ?
O1 C4 C5 C6 . . . . -178.5(2) ?
C3 C4 C5 C6 . . . . 1.5(3) ?
C4 C5 C6 C1 . . . . -0.5(4) ?
C2 C1 C6 C5 . . . . -0.7(3) ?
N1 C1 C6 C5 . . . . 178.3(2) ?
N1 C7 C8 C9 . . . . 179.48(18) ?
N1 C7 C8 C13 . . . . -0.5(3) ?
C7 C8 C9 C10 . . . . 178.19(19) ?
C13 C8 C9 C10 . . . . -1.8(3) ?
C8 C9 C10 C11 . . . . 0.7(3) ?
C9 C10 C11 N2 . . . . 177.9(2) ?
C9 C10 C11 C12 . . . . -0.4(3) ?
N2 C11 C12 C13 . . . . -177.0(2) ?
C10 C11 C12 C13 . . . . 1.4(3) ?
C11 C12 C13 O2 . . . . 177.4(2) ?
C11 C12 C13 C8 . . . . -2.5(3) ?
C7 C8 C13 O2 . . . . 2.8(3) ?
C9 C8 C13 O2 . . . . -177.25(18) ?
C7 C8 C13 C12 . . . . -177.39(19) ?
C9 C8 C13 C12 . . . . 2.6(3) ?
C8 C7 N1 C1 . . . . 176.75(18) ?
C6 C1 N1 C7 . . . . -179.4(2) ?
C2 C1 N1 C7 . . . . -0.5(3) ?
C12 C11 N2 C15 . . . . -177.6(2) ?
C10 C11 N2 C15 . . . . 4.1(4) ?
C12 C11 N2 C14 . . . . -0.5(4) ?
C10 C11 N2 C14 . . . . -178.9(2) ?
C16B C15 N2 C11 . . . . 110.8(10) ?
C16A C15 N2 C11 . . . . 83.7(6) ?
C16B C15 N2 C14 . . . . -66.3(10) ?
C16A C15 N2 C14 . . . . -93.5(6) ?
C17 C14 N2 C11 . . . . -81.1(3) ?
C17 C14 N2 C15 . . . . 96.1(3) ?
