#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/92/2209297.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_2209297
loop_
_publ_author_name
'Cheng, Kui'
'Zhu, Hai-Liang'
'Li, Zhi-Bin'
'Yan, Zheng'
_publ_section_title
;
 5-Chloro-2-(2-hydroxybenzylideneamino)benzonitrile
;
_journal_coeditor_code           RZ2034
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2417
_journal_page_last               o2418
_journal_paper_doi               10.1107/S1600536806018320
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H9 Cl N2 O'
_chemical_formula_moiety         'C14 H9 Cl N2 O'
_chemical_formula_sum            'C14 H9 Cl N2 O'
_chemical_formula_weight         256.68
_chemical_name_systematic
;
5-Chloro-2-(2-hydroxybenzylideneamino)benzonitrile
;
_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                 91.228(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.7060(12)
_cell_length_b                   14.372(4)
_cell_length_c                   18.225(5)
_cell_measurement_reflns_used    7961
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      25.4
_cell_measurement_theta_min      1.66
_cell_volume                     1232.4(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
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.1174
_diffrn_reflns_av_sigmaI/netI    0.0742
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9840
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         1.80
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'elongated prism'
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.260
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2299
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0735
_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)+(0.051P)²+0.9611P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.1675
_reflns_number_gt                1696
_reflns_number_total             2299
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2034.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/c'
_cod_database_code               2209297
_cod_database_fobs_code          2209297
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
C C1 0.5293(8) 0.7436(2) 0.36238(18) 0.0449(9) Uani d D 1
C C2 0.7384(8) 0.7691(3) 0.4127(2) 0.0593(11) Uani d DU 1
H H2 0.8007 0.8305 0.4150 0.071 Uiso calc R 1
C C3 0.8541(9) 0.7039(3) 0.4593(2) 0.0620(12) Uani d DU 1
H H3 0.9943 0.7214 0.4933 0.074 Uiso calc R 1
C C4 0.7651(9) 0.6127(3) 0.4564(2) 0.0677(12) Uani d DU 1
H H4 0.8457 0.5687 0.4880 0.081 Uiso calc R 1
C C5 0.5568(8) 0.5873(3) 0.4067(2) 0.0576(11) Uani d D 1
H H5 0.4955 0.5258 0.4051 0.069 Uiso calc R 1
C C6 0.4353(7) 0.6519(2) 0.35857(17) 0.0420(9) Uani d D 1
C C7 0.2192(8) 0.6226(3) 0.30670(18) 0.0401(8) Uani d . 1
H H7 0.1644 0.5604 0.3063 0.048 Uiso calc R 1
C C8 -0.1121(7) 0.6487(2) 0.21032(17) 0.0374(8) Uani d D 1
C C9 -0.2116(7) 0.5583(2) 0.20228(18) 0.0438(9) Uani d D 1
H H9 -0.1416 0.5117 0.2330 0.053 Uiso calc R 1
C C10 -0.4130(8) 0.5373(2) 0.14916(18) 0.0478(10) Uani d D 1
H H10 -0.4744 0.4762 0.1435 0.057 Uiso calc R 1
C C11 -0.5252(7) 0.6058(2) 0.10406(17) 0.0388(8) Uani d D 1
C C12 -0.4333(7) 0.6963(2) 0.11130(18) 0.0411(9) Uani d D 1
H H12 -0.5091 0.7430 0.0814 0.049 Uiso calc R 1
C C13 -0.2253(7) 0.7167(2) 0.16398(16) 0.0377(8) Uani d D 1
C C14 -0.1226(10) 0.8111(3) 0.1696(2) 0.0551(11) Uani d . 1
Cl Cl1 -0.7739(2) 0.57835(7) 0.03661(5) 0.0559(4) Uani d . 1
N N1 0.0994(6) 0.67831(19) 0.26123(15) 0.0401(7) Uani d . 1
O O1 0.4206(7) 0.81007(18) 0.31778(16) 0.0676(9) Uani d . 1
H H1 0.3521 0.7858 0.2807 0.101 Uiso calc R 1
N N2 -0.0365(11) 0.8850(3) 0.1707(2) 0.0891(14) Uani d U 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.046(2) 0.052(2) 0.0365(19) 0.0027(18) -0.0014(17) -0.0068(17)
C2 0.055(3) 0.065(3) 0.058(2) 0.002(2) -0.007(2) -0.019(2)
C3 0.047(3) 0.087(3) 0.052(2) 0.009(2) -0.006(2) -0.023(2)
C4 0.063(3) 0.085(3) 0.055(3) 0.012(2) -0.012(2) 0.009(2)
C5 0.060(3) 0.060(3) 0.053(2) 0.002(2) -0.005(2) 0.011(2)
C6 0.042(2) 0.051(2) 0.0330(19) 0.0030(17) 0.0059(16) -0.0006(17)
C7 0.043(2) 0.0438(19) 0.0341(19) -0.0025(17) 0.0024(16) -0.0017(16)
C8 0.043(2) 0.0384(19) 0.0312(17) 0.0019(16) -0.0005(16) -0.0056(15)
C9 0.055(2) 0.0326(19) 0.043(2) 0.0005(17) -0.0054(18) 0.0015(15)
C10 0.058(3) 0.037(2) 0.047(2) -0.0044(18) -0.0032(19) -0.0090(17)
C11 0.038(2) 0.048(2) 0.0307(17) -0.0019(16) 0.0021(15) -0.0105(15)
C12 0.044(2) 0.043(2) 0.0365(19) 0.0077(16) -0.0010(16) -0.0006(15)
C13 0.045(2) 0.0328(18) 0.0354(18) -0.0020(16) 0.0032(16) -0.0031(15)
C14 0.072(3) 0.040(2) 0.053(2) -0.004(2) -0.014(2) 0.0040(18)
Cl1 0.0512(6) 0.0660(7) 0.0501(6) -0.0012(5) -0.0110(4) -0.0148(5)
N1 0.0461(18) 0.0398(16) 0.0344(15) 0.0001(14) 0.0005(14) -0.0037(13)
O1 0.094(2) 0.0423(15) 0.0649(19) -0.0081(15) -0.0241(17) -0.0048(14)
N2 0.126(4) 0.043(2) 0.096(3) -0.016(2) -0.036(3) 0.008(2)
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
O1 C1 C2 117.9(3)
O1 C1 C6 121.7(3)
C2 C1 C6 120.4(3)
C3 C2 C1 119.9(4)
C3 C2 H2 120.1
C1 C2 H2 120.1
C2 C3 C4 120.8(4)
C2 C3 H3 119.6
C4 C3 H3 119.6
C5 C4 C3 119.4(4)
C5 C4 H4 120.3
C3 C4 H4 120.3
C4 C5 C6 121.2(4)
C4 C5 H5 119.4
C6 C5 H5 119.4
C1 C6 C5 118.3(3)
C1 C6 C7 122.0(3)
C5 C6 C7 119.7(3)
N1 C7 C6 122.7(3)
N1 C7 H7 118.6
C6 C7 H7 118.6
C9 C8 C13 118.0(3)
C9 C8 N1 125.7(3)
C13 C8 N1 116.3(3)
C10 C9 C8 120.4(3)
C10 C9 H9 119.8
C8 C9 H9 119.8
C9 C10 C11 120.8(3)
C9 C10 H10 119.6
C11 C10 H10 119.6
C12 C11 C10 120.1(3)
C12 C11 Cl1 119.4(2)
C10 C11 Cl1 120.4(2)
C11 C12 C13 118.8(3)
C11 C12 H12 120.6
C13 C12 H12 120.6
C12 C13 C8 121.8(3)
C12 C13 C14 118.5(3)
C8 C13 C14 119.7(3)
N2 C14 C13 176.7(5)
C7 N1 C8 122.2(3)
C1 O1 H1 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.348(4)
C1 C2 1.381(4)
C1 C6 1.392(4)
C2 C3 1.370(4)
C2 H2 0.9300
C3 C4 1.377(4)
C3 H3 0.9300
C4 C5 1.370(4)
C4 H4 0.9300
C5 C6 1.392(4)
C5 H5 0.9300
C6 C7 1.437(5)
C7 N1 1.275(4)
C7 H7 0.9300
C8 C9 1.387(3)
C8 C13 1.390(3)
C8 N1 1.412(4)
C9 C10 1.374(4)
C9 H9 0.9300
C10 C11 1.380(4)
C10 H10 0.9300
C11 C12 1.376(3)
C11 Cl1 1.725(3)
C12 C13 1.387(3)
C12 H12 0.9300
C13 C14 1.443(5)
C14 N2 1.137(5)
O1 H1 0.8200
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
O1 H1 N1 . 0.82 1.98 2.620(4) 134.8
C10 H10 O1 2_545 0.93 2.50 3.321(4) 147.3
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654973
