#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/98/2229823.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_2229823
loop_
_publ_author_name
'Yu, Yu-Ye'
_publ_section_title
;
 6-Methoxy-2-[(E)-phenyliminomethyl]phenol
;
_journal_coeditor_code           RZ2565
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o889
_journal_paper_doi               10.1107/S1600536811009135
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H13 N O2'
_chemical_formula_moiety         'C14 H13 N O2'
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25
_chemical_name_systematic
;
6-Methoxy-2-[(E)-phenyliminomethyl]phenol
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0882(4)
_cell_length_b                   9.1862(5)
_cell_length_c                   21.0800(12)
_cell_measurement_reflns_used    5745
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.98
_cell_measurement_theta_min      2.42
_cell_volume                     1178.95(12)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker APEXII area-detector'
_diffrn_measurement_method       'φ and 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  0.0811
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11856
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2006)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.179
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.252
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1190
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0455
_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)+(0.0787P)²+0.4631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1403
_reflns_number_gt                1007
_reflns_number_total             1190
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2565.cif
_cod_data_source_block           I
_cod_database_code               2229823
_cod_database_fobs_code          2229823
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.1467(5) 0.8849(3) 0.19232(12) 0.0471(6) Uani d . 1 . .
O O2 -0.0125(4) 1.0344(2) 0.09751(11) 0.0546(6) Uani d . 1 . .
H H2B 0.1106 0.9995 0.1017 0.066 Uiso calc R 1 . .
C C6 -0.1608(5) 0.9260(3) 0.09144(13) 0.0425(7) Uani d . 1 . .
O O1 -0.3287(4) 1.0709(2) 0.01403(10) 0.0539(6) Uani d . 1 . .
C C1 -0.1531(6) 0.7999(3) 0.12880(14) 0.0466(7) Uani d . 1 . .
C C5 -0.3315(6) 0.9420(3) 0.04705(14) 0.0454(7) Uani d . 1 . .
C C7 0.2914(5) 0.8685(3) 0.24514(15) 0.0456(7) Uani d . 1 . .
C C10 0.5867(6) 0.8458(5) 0.34404(19) 0.0637(10) Uani d . 1 . .
H H10A 0.6870 0.8378 0.3771 0.076 Uiso calc R 1 . .
C C4 -0.4870(6) 0.8348(4) 0.03963(15) 0.0537(8) Uani d . 1 . .
H H4A -0.5999 0.8468 0.0104 0.064 Uiso calc R 1 . .
C C12 0.0067(6) 0.7846(4) 0.17918(15) 0.0496(8) Uani d . 1 . .
H H12A 0.0082 0.6993 0.2029 0.060 Uiso calc R 1 . .
C C2 -0.3120(6) 0.6922(4) 0.12031(15) 0.0551(9) Uani d . 1 . .
H H2A -0.3069 0.6085 0.1451 0.066 Uiso calc R 1 . .
C C8 0.2343(6) 0.7914(4) 0.30001(15) 0.0510(8) Uani d . 1 . .
H H8A 0.0970 0.7477 0.3034 0.061 Uiso calc R 1 . .
C C13 0.4930(7) 0.9357(4) 0.24102(17) 0.0548(8) Uani d . 1 . .
H H13A 0.5290 0.9899 0.2052 0.066 Uiso calc R 1 . .
C C3 -0.4755(7) 0.7075(4) 0.07616(16) 0.0581(9) Uani d . 1 . .
H H3A -0.5783 0.6338 0.0704 0.070 Uiso calc R 1 . .
C C14 -0.5226(7) 1.1074(5) -0.0198(2) 0.0693(11) Uani d . 1 . .
H H14A -0.5026 1.1992 -0.0408 0.104 Uiso calc R 1 . .
H H14B -0.6436 1.1144 0.0093 0.104 Uiso calc R 1 . .
H H14C -0.5530 1.0333 -0.0507 0.104 Uiso calc R 1 . .
C C9 0.3840(6) 0.7807(4) 0.34918(17) 0.0578(9) Uani d . 1 . .
H H9A 0.3475 0.7295 0.3858 0.069 Uiso calc R 1 . .
C C11 0.6421(6) 0.9225(4) 0.29039(19) 0.0647(10) Uani d . 1 . .
H H11A 0.7798 0.9655 0.2872 0.078 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C12 N1 C7 . . 120.1(3) ?
C6 O2 H2B . . 109.5 ?
O2 C6 C1 . . 122.3(3) ?
O2 C6 C5 . . 118.7(3) ?
C1 C6 C5 . . 119.0(3) ?
C5 O1 C14 . . 116.6(3) ?
C2 C1 C6 . . 119.4(3) ?
C2 C1 C12 . . 119.4(3) ?
C6 C1 C12 . . 121.0(3) ?
O1 C5 C4 . . 124.6(3) ?
O1 C5 C6 . . 114.7(3) ?
C4 C5 C6 . . 120.7(3) ?
C13 C7 C8 . . 120.0(3) ?
C13 C7 N1 . . 117.0(3) ?
C8 C7 N1 . . 123.0(3) ?
C11 C10 C9 . . 120.5(4) ?
C11 C10 H10A . . 119.7 ?
C9 C10 H10A . . 119.7 ?
C5 C4 C3 . . 120.0(3) ?
C5 C4 H4A . . 120.0 ?
C3 C4 H4A . . 120.0 ?
N1 C12 C1 . . 122.3(3) ?
N1 C12 H12A . . 118.8 ?
C1 C12 H12A . . 118.8 ?
C3 C2 C1 . . 121.2(3) ?
C3 C2 H2A . . 119.4 ?
C1 C2 H2A . . 119.4 ?
C9 C8 C7 . . 119.4(3) ?
C9 C8 H8A . . 120.3 ?
C7 C8 H8A . . 120.3 ?
C7 C13 C11 . . 119.8(3) ?
C7 C13 H13A . . 120.1 ?
C11 C13 H13A . . 120.1 ?
C2 C3 C4 . . 119.7(3) ?
C2 C3 H3A . . 120.1 ?
C4 C3 H3A . . 120.1 ?
O1 C14 H14A . . 109.5 ?
O1 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O1 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C10 C9 C8 . . 120.1(3) ?
C10 C9 H9A . . 120.0 ?
C8 C9 H9A . . 120.0 ?
C10 C11 C13 . . 120.2(3) ?
C10 C11 H11A . . 119.9 ?
C13 C11 H11A . . 119.9 ?
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
N1 C12 . 1.285(4) ?
N1 C7 . 1.428(4) ?
O2 C6 . 1.350(4) ?
O2 H2B . 0.8200 ?
C6 C1 . 1.401(4) ?
C6 C5 . 1.406(4) ?
O1 C5 . 1.374(4) ?
O1 C14 . 1.419(4) ?
C1 C2 . 1.396(5) ?
C1 C12 . 1.447(5) ?
C5 C4 . 1.375(5) ?
C7 C13 . 1.377(5) ?
C7 C8 . 1.400(5) ?
C10 C11 . 1.374(6) ?
C10 C9 . 1.375(5) ?
C10 H10A . 0.9300 ?
C4 C3 . 1.402(5) ?
C4 H4A . 0.9300 ?
C12 H12A . 0.9300 ?
C2 C3 . 1.370(5) ?
C2 H2A . 0.9300 ?
C8 C9 . 1.384(5) ?
C8 H8A . 0.9300 ?
C13 C11 . 1.386(5) ?
C13 H13A . 0.9300 ?
C3 H3A . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C9 H9A . 0.9300 ?
C11 H11A . 0.9300 ?
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
C9 H9A O1 3_545 0.93 2.57 3.485(4) 168
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 19770371
