#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/07/2210737.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_2210737
loop_
_publ_author_name
'Akitsu, Takashiro'
'Einaga, Yasuaki'
_publ_section_title
;
 A chiral photochromic Schiff base:
 (R)-4-bromo-2-[(1-phenylethyl)iminomethyl]phenol
;
_journal_coeditor_code           OB2054
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4315
_journal_page_last               o4317
_journal_paper_doi               10.1107/S1600536806034891
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H14 Br N O'
_chemical_formula_moiety         'C15 H14 Br N O'
_chemical_formula_sum            'C15 H14 Br N O'
_chemical_formula_weight         304.18
_chemical_name_systematic
;
(R)-4-bromo-2-[(1-phenylethyl)iminomethyl]phenol
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 129.07(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.955(8)
_cell_length_b                   5.795(3)
_cell_length_c                   14.611(7)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      13.8
_cell_measurement_theta_min      10.0
_cell_volume                     1377.5(13)
_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_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku AFC-7R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1130
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            1907
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         2.50
_diffrn_standards_decay_%        1.37
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.972
_exptl_absorpt_correction_T_max  0.552
_exptl_absorpt_correction_T_min  0.396
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.487
_refine_ls_abs_structure_details 'Flack (1983), no Friedel pairs'
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1743
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0456
_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)+(0.0737P)²+0.6987P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1281
_reflns_number_gt                1425
_reflns_number_total             1743
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob2054.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2210737
_cod_database_fobs_code          2210737
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
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
Br Br1 0.41682(3) 0.53391(18) 0.26315(5) 0.0735(3) Uani d . 1
O O1 0.0909(2) 0.0538(10) 0.0179(4) 0.0722(11) Uani d . 1
H H1A 0.0534 0.1339 -0.0359 0.087 Uiso d R 1
N N1 0.0233(3) 0.4037(8) -0.1245(4) 0.0537(10) Uani d . 1
C C1 0.1626(4) 0.1602(10) 0.0688(5) 0.0546(11) Uani d . 1
C C2 0.2339(4) 0.0600(15) 0.1653(6) 0.0665(15) Uani d . 1
H H2A 0.2311 -0.0820 0.1923 0.079 Uiso calc R 1
C C3 0.3094(4) 0.1662(11) 0.2228(5) 0.0628(13) Uani d . 1
H H3A 0.3570 0.0967 0.2879 0.076 Uiso calc R 1
C C4 0.3134(3) 0.3775(11) 0.1822(5) 0.0545(12) Uani d . 1
C C5 0.2436(3) 0.4829(9) 0.0853(4) 0.0525(13) Uani d . 1
H H5A 0.2473 0.6240 0.0585 0.060 Uiso calc R 1
C C6 0.1675(3) 0.3757(10) 0.0278(4) 0.0491(10) Uani d . 1
C C7 0.0935(3) 0.4913(9) -0.0721(4) 0.0525(13) Uani d . 1
H H7A 0.0983 0.6325 -0.0976 0.060 Uiso calc R 1
C C8 -0.0494(3) 0.5287(15) -0.2258(4) 0.0565(10) Uani d . 1
H H8A -0.0309 0.6686 -0.2408 0.066 Uiso calc R 1
C C9 -0.1028(4) 0.5971(13) -0.1937(6) 0.0722(19) Uani d . 1
H H9A -0.0712 0.6887 -0.1232 0.088 Uiso calc R 1
H H9B -0.1221 0.4608 -0.1806 0.088 Uiso calc R 1
H H9C -0.1489 0.6851 -0.2569 0.088 Uiso calc R 1
C C10 -0.0915(3) 0.3713(11) -0.3323(5) 0.0567(12) Uani d . 1
C C11 -0.0850(5) 0.4105(15) -0.4202(6) 0.0746(17) Uani d . 1
H H11A -0.0565 0.5396 -0.4150 0.092 Uiso calc R 1
C C12 -0.1192(6) 0.265(2) -0.5129(7) 0.100(3) Uani d . 1
H H12A -0.1145 0.2969 -0.5708 0.121 Uiso calc R 1
C C13 -0.1609(6) 0.071(2) -0.5222(6) 0.099(3) Uani d . 1
H H13A -0.1827 -0.0318 -0.5845 0.115 Uiso calc R 1
C C14 -0.1696(4) 0.031(2) -0.4378(6) 0.0879(18) Uani d . 1
H H14A -0.1999 -0.0952 -0.4450 0.106 Uiso calc R 1
C C15 -0.1339(4) 0.1760(13) -0.3433(6) 0.0720(16) Uani d . 1
H H15A -0.1381 0.1425 -0.2851 0.088 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'
Br Br -0.2901 2.4595 '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
C1 O1 H1A 109.5 ?
C7 N1 C8 118.8(5) yes
O1 C1 C2 119.2(5) ?
O1 C1 C6 121.9(5) no
C2 C1 C6 118.9(6) ?
C1 C2 C3 121.4(7) ?
C1 C2 H2A 119.3 ?
C3 C2 H2A 119.3 ?
C4 C3 C2 119.1(6) ?
C4 C3 H3A 120.4 ?
C2 C3 H3A 120.4 ?
C5 C4 C3 121.3(5) ?
C5 C4 Br1 118.5(4) ?
C3 C4 Br1 120.1(5) ?
C4 C5 C6 119.3(5) ?
C4 C5 H5A 120.3 ?
C6 C5 H5A 120.3 ?
C5 C6 C1 119.9(5) ?
C5 C6 C7 119.2(5) no
C1 C6 C7 120.9(5) ?
N1 C7 C6 121.3(5) yes
N1 C7 H7A 119.3 ?
C6 C7 H7A 119.3 ?
N1 C8 C9 108.2(4) no
N1 C8 C10 107.4(6) no
C9 C8 C10 114.2(5) ?
N1 C8 H8A 109.0 ?
C9 C8 H8A 109.0 ?
C10 C8 H8A 109.0 ?
C8 C9 H9A 109.5 ?
C8 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
C8 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
C15 C10 C11 117.1(6) ?
C15 C10 C8 121.8(5) ?
C11 C10 C8 121.0(6) ?
C12 C11 C10 121.5(8) ?
C12 C11 H11A 119.2 ?
C10 C11 H11A 119.2 ?
C11 C12 C13 120.7(8) ?
C11 C12 H12A 119.7 ?
C13 C12 H12A 119.7 ?
C14 C13 C12 118.8(9) ?
C14 C13 H13A 120.6 ?
C12 C13 H13A 120.6 ?
C15 C14 C13 120.4(10) ?
C15 C14 H14A 119.8 ?
C13 C14 H14A 119.8 ?
C14 C15 C10 121.5(7) ?
C14 C15 H15A 119.3 ?
C10 C15 H15A 119.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C4 1.921(6) yes
O1 C1 1.335(7) yes
O1 H1A 0.8199 ?
N1 C7 1.261(7) yes
N1 C8 1.482(7) yes
C1 C2 1.379(9) ?
C1 C6 1.416(8) ?
C2 C3 1.384(10) ?
C2 H2A 0.9300 ?
C3 C4 1.385(9) ?
C3 H3A 0.9300 ?
C4 C5 1.381(8) ?
C5 C6 1.395(7) ?
C5 H5A 0.9300 ?
C6 C7 1.459(7) ?
C7 H7A 0.9300 ?
C8 C9 1.514(9) ?
C8 C10 1.517(9) ?
C8 H8A 0.9800 ?
C9 H9A 0.9600 ?
C9 H9B 0.9600 ?
C9 H9C 0.9600 ?
C10 C15 1.384(10) ?
C10 C11 1.392(9) ?
C11 C12 1.355(13) ?
C11 H11A 0.9300 ?
C12 C13 1.379(16) ?
C12 H12A 0.9300 ?
C13 C14 1.376(14) ?
C13 H13A 0.9300 ?
C14 C15 1.367(12) ?
C14 H14A 0.9300 ?
C15 H15A 0.9300 ?
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
_geom_hbond_publ_flag
O1 H1A N1 0.81 1.88 2.593(7) 146 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
O1 C1 C2 C3 -178.4(6) ?
C6 C1 C2 C3 0.4(9) ?
C1 C2 C3 C4 -0.1(10) ?
C2 C3 C4 C5 -0.4(9) ?
C2 C3 C4 Br1 178.0(5) ?
C3 C4 C5 C6 0.7(7) ?
Br1 C4 C5 C6 -177.8(4) ?
C4 C5 C6 C1 -0.4(7) ?
C4 C5 C6 C7 177.9(5) ?
O1 C1 C6 C5 178.7(5) ?
C2 C1 C6 C5 -0.1(8) ?
O1 C1 C6 C7 0.4(8) no
C2 C1 C6 C7 -178.4(6) ?
C8 N1 C7 C6 -179.6(5) yes
C5 C6 C7 N1 -178.0(5) ?
C1 C6 C7 N1 0.3(7) yes
C7 N1 C8 C9 -115.9(6) yes
C7 N1 C8 C10 120.4(5) yes
N1 C8 C10 C15 71.2(7) ?
C9 C8 C10 C15 -48.7(8) ?
N1 C8 C10 C11 -105.0(6) ?
C9 C8 C10 C11 135.1(7) ?
C15 C10 C11 C12 0.6(10) ?
C8 C10 C11 C12 176.9(7) ?
C10 C11 C12 C13 -0.9(12) ?
C11 C12 C13 C14 2.2(13) ?
C12 C13 C14 C15 -3.3(14) ?
C13 C14 C15 C10 3.1(13) ?
C11 C10 C15 C14 -1.6(10) ?
C8 C10 C15 C14 -178.0(7) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655070
