#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/44/2014478.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_2014478
loop_
_publ_author_name
'Akitsu, Takashiro'
'Takeuchi, Yuiri'
'Einaga, Yasuaki'
_publ_section_title
;
 Racemic 3,5-dichloro-2-{[(1-phenylethyl)imino]methyl}phenol
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o801
_journal_page_last               o802
_journal_paper_doi               10.1107/S0108270104017354
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C15 H13 Cl2 N O'
_chemical_formula_moiety         'C15 H13 Cl2 N O'
_chemical_formula_sum            'C15 H13 Cl2 N O'
_chemical_formula_weight         294.16
_chemical_name_systematic
;
3,5-dichloro-2-{[(1-phenylethyl)imino]methyl}phenol
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 113.99(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.395(8)
_cell_length_b                   9.463(5)
_cell_length_c                   15.571(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298.0(10)
_cell_measurement_theta_max      12.3
_cell_measurement_theta_min      10.0
_cell_volume                     2880(2)
_computing_cell_refinement       'WinAFC Diffractometer Control Software'
_computing_data_collection
'WinAFC Diffractometer Control Software (Rigaku, 1999)'
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 2001)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Rigaku AFC-7R'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3867
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_standards_decay_%        0.54
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.441
_exptl_absorpt_correction_T_max  0.802
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1216.0
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1468
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.064P)²+1.9396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1804
_reflns_number_gt                1468
_reflns_number_total             3323
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ga1070.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2014478
_cod_database_fobs_code          2014478
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y,1/2-z
-x,-y,-z
x,-y,1/2+z
1/2+x,1/2+y,z
1/2-x,1/2+y,1/2-z
1/2-x,1/2-y,-z
1/2+x,1/2-y,1/2+z
loop_
_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
_atom_site_type_symbol
Cl1 1.15758(4) 0.91050(10) 0.56244(8) 0.0956(4) Uani d . 1.00 . . Cl
Cl2 1.03127(6) 1.39080(10) 0.39830(10) 0.1200(5) Uani d . 1.00 . . Cl
O1 1.03450(10) 0.7741(3) 0.4275(2) 0.0806(7) Uani d . 1.00 . . O
N1 0.91040(10) 0.7751(3) 0.2979(2) 0.0712(8) Uani d . 1.00 . . N
C1 1.03280(10) 0.9157(2) 0.4183(2) 0.0609(8) Uani d . 1.00 . . C
C2 1.08891(8) 0.9932(2) 0.47770(10) 0.0659(8) Uani d . 1.00 . . C
C3 1.08869(9) 1.1397(2) 0.47090(10) 0.0690(9) Uani d . 1.00 . . C
C4 1.03230(10) 1.2087(2) 0.4047(2) 0.0737(9) Uani d . 1.00 . . C
C5 0.97617(9) 1.1312(2) 0.34540(10) 0.0749(10) Uani d . 1.00 . . C
C6 0.97640(8) 0.9847(2) 0.35210(10) 0.0633(8) Uani d . 1.00 . . C
C7 0.9151(2) 0.9082(4) 0.2914(2) 0.0734(9) Uani d . 1.00 . . C
C8 0.8449(2) 0.7071(4) 0.2379(2) 0.0800(10) Uani d . 1.00 . . C
C9 0.81150(10) 0.6553(3) 0.30060(10) 0.0624(8) Uani d . 1.00 . . C
C10 0.75600(10) 0.7300(2) 0.3023(2) 0.0790(10) Uani d . 1.00 . . C
C11 0.72620(10) 0.6888(3) 0.3627(2) 0.1000(10) Uani d . 1.00 . . C
C12 0.7518(2) 0.5728(3) 0.4214(2) 0.0990(10) Uani d . 1.00 . . C
C13 0.8072(2) 0.4981(2) 0.4196(2) 0.0920(10) Uani d . 1.00 . . C
C14 0.83700(10) 0.5393(2) 0.3592(2) 0.0771(10) Uani d . 1.00 . . C
C15 0.8592(2) 0.5948(5) 0.1802(3) 0.111(2) Uani d . 1.00 . . C
H1 1.1271 1.1925 0.5115 0.0831 Uiso calc . 1.00 . . H
H2 0.9377 1.1783 0.3002 0.0904 Uiso calc . 1.00 . . H
H3 0.8778 0.9594 0.2463 0.0889 Uiso calc . 1.00 . . H
H4 0.8161 0.7759 0.1963 0.0953 Uiso calc . 1.00 . . H
H5 0.7384 0.8091 0.2621 0.0958 Uiso calc . 1.00 . . H
H6 0.6882 0.7397 0.3637 0.1199 Uiso calc . 1.00 . . H
H7 0.7315 0.5447 0.4627 0.1175 Uiso calc . 1.00 . . H
H8 0.8247 0.4188 0.4598 0.1113 Uiso calc . 1.00 . . H
H9 0.8749 0.4884 0.3582 0.0929 Uiso calc . 1.00 . . H
H10 0.8178 0.5514 0.1396 0.1342 Uiso calc . 1.00 . . H
H11 0.8814 0.6353 0.1442 0.1342 Uiso calc . 1.00 . . H
H12 0.8886 0.5244 0.2211 0.1342 Uiso calc . 1.00 . . H
H13 0.9911 0.7383 0.3795 0.0972 Uiso calc . 1.00 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Cl Cl 0.148 0.159
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, 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
C1 O1 H13 106.6 no
C7 N1 C8 117.8(3) yes
O1 C1 C2 118.4(2) no
O1 C1 C6 121.6(2) yes
C2 C1 C6 120.0(2) no
Cl1 C2 C1 120.7(2) no
Cl1 C2 C3 119.30(10) no
C1 C2 C3 120.00(10) no
C2 C3 C4 120.0(2) no
C2 C3 H1 119.9 no
C4 C3 H1 120.1 no
Cl2 C4 C3 119.90(10) no
Cl2 C4 C5 120.00(10) no
C3 C4 C5 120.0(2) no
C4 C5 C6 120.0(2) no
C4 C5 H2 120.0 no
C6 C5 H2 120.0 no
C1 C6 C5 120.00(10) no
C1 C6 C7 121.9(2) no
C5 C6 C7 118.1(2) yes
N1 C7 C6 121.3(3) yes
N1 C7 H3 119.5 no
C6 C7 H3 119.2 no
N1 C8 C9 108.0(3) yes
N1 C8 C15 108.4(3) yes
N1 C8 H4 108.6 no
C9 C8 C15 115.0(3) no
C9 C8 H4 108.5 no
C15 C8 H4 108.1 no
C8 C9 C10 118.7(2) no
C8 C9 C14 121.3(2) no
C10 C9 C14 120.0(2) no
C9 C10 C11 120.0(2) no
C9 C10 H5 120.1 no
C11 C10 H5 119.9 no
C10 C11 C12 120.0(3) no
C10 C11 H6 120.0 no
C12 C11 H6 120.0 no
C11 C12 C13 120.0(3) no
C11 C12 H7 120.0 no
C13 C12 H7 120.0 no
C12 C13 C14 120.0(2) no
C12 C13 H8 120.0 no
C14 C13 H8 120.0 no
C9 C14 C13 120.0(2) no
C9 C14 H9 120.0 no
C13 C14 H9 120.0 no
C8 C15 H10 110.0 no
C8 C15 H11 109.9 no
C8 C15 H12 109.4 no
H10 C15 H11 109.7 no
H10 C15 H12 109.0 no
H11 C15 H12 108.8 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C2 . . 1.714(2) yes
Cl2 C4 . . 1.726(2) yes
O1 C1 . . 1.347(3) yes
O1 H13 . . 0.985 no
N1 C7 . . 1.271(5) yes
N1 C8 . . 1.478(4) yes
C1 C2 . . 1.390(2) no
C1 C6 . . 1.390(2) no
C2 C3 . . 1.390(3) no
C3 C4 . . 1.390(3) no
C3 H1 . . 0.950 no
C4 C5 . . 1.390(3) no
C5 C6 . . 1.390(3) no
C5 H2 . . 0.950 no
C6 C7 . . 1.460(4) no
C7 H3 . . 0.950 no
C8 C9 . . 1.507(5) no
C8 C15 . . 1.502(7) no
C8 H4 . . 0.950 no
C9 C10 . . 1.390(4) no
C9 C14 . . 1.390(3) no
C10 C11 . . 1.390(4) no
C10 H5 . . 0.950 no
C11 C12 . . 1.390(4) no
C11 H6 . . 0.950 no
C12 C13 . . 1.390(5) no
C12 H7 . . 0.950 no
C13 C14 . . 1.390(4) no
C13 H8 . . 0.950 no
C14 H9 . . 0.950 no
C15 H10 . . 0.950 no
C15 H11 . . 0.950 no
C15 H12 . . 0.950 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H13 N1 148 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
_geom_torsion_publ_flag
Cl1 C2 C1 O1 -1.7(4) no
Cl1 C2 C1 C6 177.7(2) no
Cl1 C2 C3 C4 -177.7(2) no
Cl2 C4 C3 C2 178.5(2) no
Cl2 C4 C5 C6 -178.5(2) no
O1 C1 C2 C3 -179.3(2) no
O1 C1 C6 C5 179.3(3) no
O1 C1 C6 C7 2.3(4) yes
N1 C7 C6 C1 1.3(5) yes
N1 C7 C6 C5 -175.8(3) no
N1 C8 C9 C10 104.9(3) no
N1 C8 C9 C14 -72.0(3) no
C1 C2 C3 C4 0.0(4) no
C1 C6 C5 C4 0.0(4) no
C2 C1 C6 C5 0.0(4) no
C2 C1 C6 C7 -177.1(3) no
C2 C3 C4 C5 0.0(4) no
C3 C2 C1 C6 0.0(4) no
C3 C4 C5 C6 0.0(4) no
C4 C5 C6 C7 177.2(3) no
C6 C7 N1 C8 176.2(3) yes
C7 N1 C8 C9 -111.1(4) yes
C7 N1 C8 C15 123.6(4) yes
C8 C9 C10 C11 -176.9(2) no
C8 C9 C14 C13 176.8(2) no
C9 C10 C11 C12 0.0(3) no
C9 C14 C13 C12 0.0(3) no
C10 C9 C8 C15 -134.0(3) no
C10 C9 C14 C13 0.0(3) no
C10 C11 C12 C13 0.0(4) no
C11 C10 C9 C14 0.0(3) no
C11 C12 C13 C14 0.0(4) no
C14 C9 C8 C15 49.2(3) no
C14 C9 C8 C15 49.2(3) no
