#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/65/2216540.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_2216540
loop_
_publ_author_name
'Wang, Qiang'
'Wang, Da-Qi'
_publ_section_title
;
 2-[4-(Dimethylamino)benzylideneimino]phenol
;
_journal_coeditor_code           HG2356
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4838
_journal_page_last               o4838
_journal_paper_doi               10.1107/S1600536807058813
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H16 N2 O'
_chemical_formula_moiety         'C15 H16 N2 O'
_chemical_formula_sum            'C15 H16 N2 O'
_chemical_formula_weight         240.30
_chemical_name_systematic
;
2-[4-(Dimethylamino)benzylideneimino]phenol
;
_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                90.00
_cell_angle_beta                 96.765(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3549(17)
_cell_length_b                   9.598(3)
_cell_length_c                   21.211(6)
_cell_measurement_reflns_used    1366
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.789
_cell_measurement_theta_min      2.333
_cell_volume                     1284.7(6)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997b)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6513
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9782
_exptl_absorpt_correction_T_min  0.9645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2262
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0451
_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)+(0.0594P)²+0.1997P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1385
_reflns_number_gt                1269
_reflns_number_total             2262
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2356.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2216540
_cod_database_fobs_code          2216540
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
N N1 0.9004(3) 1.00454(18) 0.12707(8) 0.0537(5) Uani d . 1
N N2 1.1112(3) 0.5763(2) -0.09216(9) 0.0658(6) Uani d . 1
O O1 0.5504(2) 1.1421(2) 0.14064(8) 0.0830(6) Uani d . 1
H H1 0.5841 1.0870 0.1141 0.125 Uiso calc R 1
C C1 0.9087(3) 1.0960(2) 0.17941(10) 0.0512(5) Uani d . 1
C C2 0.7186(4) 1.1638(2) 0.18561(10) 0.0580(6) Uani d . 1
C C3 0.7002(4) 1.2532(3) 0.23541(12) 0.0700(7) Uani d . 1
H H3 0.5718 1.2972 0.2391 0.084 Uiso calc R 1
C C4 0.8718(5) 1.2771(3) 0.27941(12) 0.0727(7) Uani d . 1
H H4 0.8601 1.3381 0.3129 0.087 Uiso calc R 1
C C5 1.0610(4) 1.2116(3) 0.27443(12) 0.0752(7) Uani d . 1
H H5 1.1770 1.2281 0.3045 0.090 Uiso calc R 1
C C6 1.0791(4) 1.1213(2) 0.22487(11) 0.0670(7) Uani d . 1
H H6 1.2075 1.0769 0.2219 0.080 Uiso calc R 1
C C7 1.0693(4) 0.9545(2) 0.10922(10) 0.0557(6) Uani d . 1
H H7 1.1979 0.9823 0.1311 0.067 Uiso calc R 1
C C8 1.0753(3) 0.8578(2) 0.05760(9) 0.0500(5) Uani d . 1
C C9 0.8952(3) 0.8138(2) 0.01932(10) 0.0580(6) Uani d . 1
H H9 0.7637 0.8478 0.0271 0.070 Uiso calc R 1
C C10 0.9054(4) 0.7219(2) -0.02952(11) 0.0609(6) Uani d . 1
H H10 0.7810 0.6951 -0.0541 0.073 Uiso calc R 1
C C11 1.0993(3) 0.6671(2) -0.04338(9) 0.0520(6) Uani d . 1
C C12 1.2811(4) 0.7123(2) -0.00509(11) 0.0635(6) Uani d . 1
H H12 1.4132 0.6791 -0.0127 0.076 Uiso calc R 1
C C13 1.2672(3) 0.8047(3) 0.04335(10) 0.0625(6) Uani d . 1
H H13 1.3911 0.8331 0.0677 0.075 Uiso calc R 1
C C14 1.3081(4) 0.5123(3) -0.10345(12) 0.0839(8) Uani d . 1
H H14A 1.2847 0.4527 -0.1399 0.126 Uiso calc R 1
H H14B 1.3624 0.4583 -0.0670 0.126 Uiso calc R 1
H H14C 1.4087 0.5833 -0.1109 0.126 Uiso calc R 1
C C15 0.9224(4) 0.5312(3) -0.13154(12) 0.0860(8) Uani d . 1
H H15A 0.9609 0.4685 -0.1636 0.129 Uiso calc R 1
H H15B 0.8510 0.6107 -0.1515 0.129 Uiso calc R 1
H H15C 0.8300 0.4844 -0.1058 0.129 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
_geom_angle_publ_flag
C7 N1 C1 120.93(19) y
C11 N2 C14 121.8(2) y
C11 N2 C15 120.9(2) y
C14 N2 C15 117.1(2) ?
C2 O1 H1 109.5 ?
C6 C1 C2 117.9(2) ?
C6 C1 N1 127.7(2) ?
C2 C1 N1 114.4(2) ?
O1 C2 C3 120.1(2) ?
O1 C2 C1 118.7(2) y
C3 C2 C1 121.2(2) ?
C4 C3 C2 119.6(2) ?
C4 C3 H3 120.2 ?
C2 C3 H3 120.2 ?
C3 C4 C5 120.4(2) ?
C3 C4 H4 119.8 ?
C5 C4 H4 119.8 ?
C4 C5 C6 120.0(2) ?
C4 C5 H5 120.0 ?
C6 C5 H5 120.0 ?
C5 C6 C1 120.9(2) ?
C5 C6 H6 119.5 ?
C1 C6 H6 119.5 ?
N1 C7 C8 124.6(2) ?
N1 C7 H7 117.7 ?
C8 C7 H7 117.7 ?
C13 C8 C9 116.5(2) ?
C13 C8 C7 120.3(2) ?
C9 C8 C7 123.2(2) y
C10 C9 C8 122.0(2) ?
C10 C9 H9 119.0 ?
C8 C9 H9 119.0 ?
C9 C10 C11 121.5(2) ?
C9 C10 H10 119.3 ?
C11 C10 H10 119.3 ?
N2 C11 C12 121.6(2) ?
N2 C11 C10 121.9(2) ?
C12 C11 C10 116.6(2) ?
C13 C12 C11 121.0(2) ?
C13 C12 H12 119.5 ?
C11 C12 H12 119.5 ?
C12 C13 C8 122.5(2) ?
C12 C13 H13 118.7 ?
C8 C13 H13 118.7 ?
N2 C14 H14A 109.5 ?
N2 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
N2 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
N2 C15 H15A 109.5 ?
N2 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
N2 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C7 1.274(3) y
N1 C1 1.411(2) y
N2 C11 1.362(3) y
N2 C14 1.439(3) y
N2 C15 1.445(3) y
O1 C2 1.362(3) y
O1 H1 0.8200 ?
C1 C6 1.384(3) ?
C1 C2 1.392(3) ?
C2 C3 1.377(3) ?
C3 C4 1.369(3) ?
C3 H3 0.9300 ?
C4 C5 1.372(3) ?
C4 H4 0.9300 ?
C5 C6 1.377(3) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 C8 1.439(3) ?
C7 H7 0.9300 ?
C8 C13 1.387(3) ?
C8 C9 1.389(3) ?
C9 C10 1.368(3) ?
C9 H9 0.9300 ?
C10 C11 1.403(3) ?
C10 H10 0.9300 ?
C11 C12 1.400(3) ?
C12 C13 1.368(3) ?
C12 H12 0.9300 ?
C13 H13 0.9300 ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 N1 0.82 2.15 2.631(3) 117.8
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
_geom_torsion_publ_flag
C7 N1 C1 C6 -14.3(3) ?
C7 N1 C1 C2 167.72(19) ?
C6 C1 C2 O1 178.8(2) ?
N1 C1 C2 O1 -3.0(3) ?
C6 C1 C2 C3 -0.1(3) ?
N1 C1 C2 C3 178.10(18) ?
O1 C2 C3 C4 -178.3(2) ?
C1 C2 C3 C4 0.6(3) ?
C2 C3 C4 C5 -0.6(4) ?
C3 C4 C5 C6 0.1(4) ?
C4 C5 C6 C1 0.4(4) ?
C2 C1 C6 C5 -0.4(3) ?
N1 C1 C6 C5 -178.3(2) ?
C1 N1 C7 C8 178.19(18) y
N1 C7 C8 C13 -177.4(2) ?
N1 C7 C8 C9 3.4(3) ?
C13 C8 C9 C10 0.6(3) ?
C7 C8 C9 C10 179.9(2) ?
C8 C9 C10 C11 0.1(3) ?
C14 N2 C11 C12 5.7(3) ?
C15 N2 C11 C12 -179.6(2) ?
C14 N2 C11 C10 -175.4(2) ?
C15 N2 C11 C10 -0.7(3) ?
C9 C10 C11 N2 -179.6(2) ?
C9 C10 C11 C12 -0.6(3) ?
N2 C11 C12 C13 179.3(2) ?
C10 C11 C12 C13 0.3(3) ?
C11 C12 C13 C8 0.4(4) ?
C9 C8 C13 C12 -0.9(3) ?
C7 C8 C13 C12 179.8(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 237465
