#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/61/2236103.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_2236103
loop_
_publ_author_name
'Khalaji, Aliakbar Dehno'
'Fejfarová, Karla'
'Dušek, Michal'
_publ_section_title
;
 4-[(E)-(4-Ethoxyphenyl)iminomethyl]phenol
;
_journal_coeditor_code           BT5991
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2646
_journal_paper_doi               10.1107/S1600536812034253
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C15 H15 N1 O2'
_chemical_formula_moiety         'C15 H15 N1 O2'
_chemical_formula_sum            'C15 H15 N O2'
_chemical_formula_weight         241.3
_chemical_name_systematic
;
4-[(E)-(4-Ethoxyphenyl)iminomethyl]phenol
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.9155(2)
_cell_length_b                   9.4056(2)
_cell_length_c                   25.0422(5)
_cell_measurement_reflns_used    14821
_cell_measurement_temperature    120
_cell_measurement_theta_max      61.05
_cell_measurement_theta_min      3.53
_cell_volume                     2571.00(9)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material
'JANA2006 (Petříček et al., 2006)'
_computing_structure_refinement
'JANA2006 (Petříček et al., 2006)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 10.3784
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type
;
Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector
;
_diffrn_measurement_method
'Rotation method data acquisition using ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_sigmaI/netI    0.0085
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            22644
_diffrn_reflns_reduction_process
;
Integration of the CCD images was done by program CrysAlis PRO
(Agilent, 2011). The same program was used for indexing of the
crystal shape and absorption correction.
;
_diffrn_reflns_theta_full        61.14
_diffrn_reflns_theta_max         61.14
_diffrn_reflns_theta_min         3.53
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2011)
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.2463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.536
_exptl_crystal_size_mid          0.199
_exptl_crystal_size_min          0.027
_refine_diff_density_max         0.11
_refine_diff_density_min         -0.11
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.71
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_constraints    57
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1978
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.0057
_refine_ls_shift/su_mean         0.0006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/(σ²(I)+0.0025000002I²)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1033
_reflns_number_gt                1780
_reflns_number_total             1978
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            bt5991.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C15 H15 N1 O2'
_cod_database_code               2236103
_cod_database_fobs_code          2236103
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x+1/2,-y,z+1/2
3 -x,y+1/2,-z+1/2
4 x+1/2,-y+1/2,-z
5 -x,-y,-z
6 x+1/2,y,-z+1/2
7 x,-y+1/2,z+1/2
8 -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_symmetry_multiplicity
O O1 -0.08099(8) 0.58106(10) 0.55939(4) 0.0344(3) Uani d . 1 8
O O2 0.50129(8) -0.13939(9) 0.85269(3) 0.0251(3) Uani d . 1 8
N N1 0.26997(8) 0.30259(10) 0.68326(4) 0.0196(3) Uani d . 1 8
C C1 0.18053(10) 0.37189(12) 0.65100(4) 0.0200(3) Uani d . 1 8
C C2 0.06035(11) 0.32217(13) 0.64660(4) 0.0234(4) Uani d . 1 8
C C3 -0.02398(11) 0.39425(13) 0.61577(5) 0.0260(4) Uani d . 1 8
C C4 0.00974(12) 0.51683(14) 0.58837(4) 0.0259(4) Uani d . 1 8
C C5 0.12999(11) 0.56466(13) 0.59109(5) 0.0251(4) Uani d . 1 8
C C6 0.21487(11) 0.49095(12) 0.62174(5) 0.0228(4) Uani d . 1 8
C C7 -0.04877(15) 0.70560(14) 0.52934(5) 0.0357(4) Uani d . 1 8
C C8 -0.16378(16) 0.75963(18) 0.50327(7) 0.0509(5) Uani d . 1 8
C C9 0.23493(11) 0.24457(11) 0.72715(5) 0.0208(4) Uani d . 1 8
C C10 0.42099(10) 0.09397(12) 0.74119(5) 0.0198(4) Uani d . 1 8
C C11 0.48630(10) -0.00196(12) 0.77159(4) 0.0199(4) Uani d . 1 8
C C12 0.44379(10) -0.04176(12) 0.82220(4) 0.0205(4) Uani d . 1 8
C C13 0.33635(10) 0.01912(12) 0.84201(5) 0.0230(4) Uani d . 1 8
C C14 0.27084(11) 0.11386(12) 0.81106(4) 0.0228(4) Uani d . 1 8
C C15 0.31179(10) 0.15335(12) 0.76005(4) 0.0202(4) Uani d . 1 8
H H2 0.036296 0.23732 0.665154 0.028 Uiso calc R 1 8
H H3 -0.106486 0.35958 0.613196 0.0313 Uiso calc R 1 8
H H5 0.154298 0.648332 0.571861 0.0301 Uiso calc R 1 8
H H6 0.298437 0.52267 0.622731 0.0273 Uiso calc R 1 8
H H7a 0.009871 0.680691 0.502344 0.0429 Uiso calc R 1 8
H H7b -0.017107 0.776855 0.553066 0.0429 Uiso calc R 1 8
H H8a -0.144624 0.840538 0.481436 0.0764 Uiso calc R 1 8
H H8b -0.198521 0.686045 0.48144 0.0764 Uiso calc R 1 8
H H8c -0.221636 0.786824 0.530273 0.0764 Uiso calc R 1 8
H H9 0.152732 0.262562 0.738996 0.0249 Uiso calc R 1 8
H H10 0.450945 0.120386 0.706538 0.0237 Uiso calc R 1 8
H H11 0.561133 -0.041581 0.758022 0.0239 Uiso calc R 1 8
H H13 0.308026 -0.0049 0.877165 0.0276 Uiso calc R 1 8
H H14 0.196003 0.153391 0.82466 0.0273 Uiso calc R 1 8
H H2o 0.5725(16) -0.1625(16) 0.8374(6) 0.0377 Uiso d T 1 8
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0181 0.0091 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.0311 0.0180 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0492 0.0322 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C4 O1 C7 117.43(10)
C12 O2 H2o 109.1(9)
C1 N1 C9 118.37(9)
N1 C1 C2 122.33(10)
N1 C1 C6 118.86(10)
C2 C1 C6 118.78(10)
C1 C2 C3 120.40(11)
C1 C2 H2 119.8
C3 C2 H2 119.8
C2 C3 C4 120.45(11)
C2 C3 H3 119.77
C4 C3 H3 119.77
O1 C4 C3 115.84(11)
O1 C4 C5 124.54(11)
C3 C4 C5 119.61(11)
C4 C5 C6 119.73(11)
C4 C5 H5 120.14
C6 C5 H5 120.14
C1 C6 C5 120.91(11)
C1 C6 H6 119.54
C5 C6 H6 119.54
O1 C7 C8 107.38(12)
O1 C7 H7a 109.47
O1 C7 H7b 109.47
C8 C7 H7a 109.47
C8 C7 H7b 109.47
H7a C7 H7b 111.48
C7 C8 H8a 109.47
C7 C8 H8b 109.47
C7 C8 H8c 109.47
H8a C8 H8b 109.47
H8a C8 H8c 109.47
H8b C8 H8c 109.47
N1 C9 C15 124.24(10)
N1 C9 H9 117.88
C15 C9 H9 117.88
C11 C10 C15 121.02(10)
C11 C10 H10 119.49
C15 C10 H10 119.49
C10 C11 C12 120.21(10)
C10 C11 H11 119.89
C12 C11 H11 119.9
O2 C12 C11 122.68(10)
O2 C12 C13 117.95(10)
C11 C12 C13 119.35(10)
C12 C13 C14 120.02(11)
C12 C13 H13 119.99
C14 C13 H13 119.99
C13 C14 C15 121.12(10)
C13 C14 H14 119.44
C15 C14 H14 119.44
C9 C15 C10 122.37(10)
C9 C15 C14 119.18(10)
C10 C15 C14 118.24(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.3684(15)
O1 C7 1.4360(16)
O2 C12 1.3492(14)
O2 H2o 0.894(17)
N1 C1 1.4250(14)
N1 C9 1.2853(14)
C1 C2 1.3971(16)
C1 C6 1.3897(16)
C2 C3 1.3795(17)
C2 H2 0.96
C3 C4 1.3913(17)
C3 H3 0.96
C4 C5 1.3892(17)
C5 C6 1.3887(16)
C5 H5 0.96
C6 H6 0.96
C7 C8 1.504(2)
C7 H7a 0.96
C7 H7b 0.96
C8 H8a 0.96
C8 H8b 0.96
C8 H8c 0.96
C9 C15 1.4557(16)
C9 H9 0.96
C10 C11 1.3791(16)
C10 C15 1.3985(15)
C10 H10 0.96
C11 C12 1.4006(15)
C11 H11 0.96
C12 C13 1.3961(16)
C13 C14 1.3807(16)
C13 H13 0.96
C14 C15 1.4033(16)
C14 H14 0.96
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
_geom_hbond_publ_flag
C7 H7b O2 6_466 0.96 2.50 3.3393(15) 146.6 yes
O2 H2o N1 3_646 0.894(17) 1.825(17) 2.7098(12) 170.0(14) 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
C4 O1 C7 C8 -177.51(11)
C9 N1 C1 C2 -35.10(15)
C9 N1 C1 C6 146.67(11)
N1 C9 C15 C10 -15.04(18)
N1 C9 C15 C14 170.16(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12624656
