#------------------------------------------------------------------------------
#$Date: 2023-01-30 12:25:39 +0200 (Mon, 30 Jan 2023) $
#$Revision: 280668 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/66/8106624.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106624
loop_
_publ_author_name
'Salman, Mahmoud'
'Abu-Yamin, Abdel Aziz'
'Sarairah, Ibrahim'
'Ibrahim, Alhawarin'
'AlDamen, Murad A.'
_publ_section_title
;
 The crystal structure of ethyl 4-((2-hydroxybenzyl)amino)benzoate, a
 Schiff base, C16H17NO3
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              631
_journal_page_last               632
_journal_paper_doi               10.1515/ncrs-2016-0383
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C16 H17 N O3'
_chemical_formula_sum            'C16 H17 N O3'
_chemical_formula_weight         271.30
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                94.468(8)
_cell_angle_beta                 91.063(7)
_cell_angle_gamma                116.644(10)
_cell_formula_units_Z            2
_cell_length_a                   7.5445(7)
_cell_length_b                   8.3326(9)
_cell_length_c                   12.4291(10)
_cell_measurement_reflns_used    1383
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      29.1212
_cell_measurement_theta_min      3.0200
_cell_volume                     695.01(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 16.0534
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -42.00   50.00   1.0000   13.3700
omega____ theta____ kappa____ phi______ frames
    -      -15.2878   77.0000  -30.0000 92

#__ type_ start__ end____ width___ exp.time_
  2 omega  -83.00   11.00   1.0000   13.3700
omega____ theta____ kappa____ phi______ frames
    -      -15.2878  -77.0000 -150.0000 94

#__ type_ start__ end____ width___ exp.time_
  3 omega  -34.00    6.00   1.0000   13.3700
omega____ theta____ kappa____ phi______ frames
    -      -15.2878  -77.0000   90.0000 40

#__ type_ start__ end____ width___ exp.time_
  4 omega  -27.00    5.00   1.0000   13.3700
omega____ theta____ kappa____ phi______ frames
    -      -15.2878  -77.0000    0.0000 32

#__ type_ start__ end____ width___ exp.time_
  5 omega  -51.00   31.00   1.0000   13.3700
omega____ theta____ kappa____ phi______ frames
    -       15.9128  -38.0000   60.0000 82
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0144263000
_diffrn_orient_matrix_UB_12      0.0780885000
_diffrn_orient_matrix_UB_13      -0.0027027000
_diffrn_orient_matrix_UB_21      -0.1041696000
_diffrn_orient_matrix_UB_22      -0.0536431000
_diffrn_orient_matrix_UB_23      0.0005119000
_diffrn_orient_matrix_UB_31      0.0065802000
_diffrn_orient_matrix_UB_32      0.0134086000
_diffrn_orient_matrix_UB_33      0.0572789000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4651
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.014
_diffrn_reflns_theta_max         25.014
_diffrn_reflns_theta_min         3.026
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.9203
_exptl_crystal_size_mid          0.3917
_exptl_crystal_size_min          0.2015
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0554P)²+0.0278P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1240
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1732
_reflns_number_total             2434
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2016-0383_suppl.cif
_cod_data_source_block           exp_1282
_cod_database_code               8106624
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.2431(2) 0.64218(19) 1.14652(11) 0.0598(4) Uani 1 1 d . . . . .
O1 O 0.2129(2) 0.33784(19) 0.43007(10) 0.0582(4) Uani 1 1 d . . . . .
N1 N 0.2399(2) 0.8356(2) 0.84692(12) 0.0444(4) Uani 1 1 d . . . . .
O2 O 0.3272(2) 0.5998(2) 0.35672(11) 0.0696(5) Uani 1 1 d . . . . .
C12 C 0.5806(3) 0.8033(2) 0.93366(14) 0.0422(5) Uani 1 1 d . . . . .
H12 H 0.5819 0.8437 0.8659 0.051 Uiso 1 1 calc R . . . .
C7 C 0.2496(2) 0.7549(2) 0.74763(13) 0.0395(5) Uani 1 1 d . . . . .
C16 C 0.4130(3) 0.6923(2) 1.09167(14) 0.0419(5) Uani 1 1 d . . . . .
C11 C 0.4093(2) 0.7500(2) 0.98980(13) 0.0375(5) Uani 1 1 d . . . . .
C10 C 0.2226(3) 0.7537(2) 0.94677(14) 0.0429(5) Uani 1 1 d . . . . .
H10A H 0.1178 0.6307 0.9359 0.051 Uiso 1 1 calc R . . . .
H10B H 0.1822 0.8184 1.0013 0.051 Uiso 1 1 calc R . . . .
C4 C 0.2609(3) 0.5933(2) 0.54248(14) 0.0427(5) Uani 1 1 d . . . . .
C8 C 0.1917(3) 0.5702(2) 0.73036(14) 0.0445(5) Uani 1 1 d . . . . .
H8 H 0.1479 0.4990 0.7876 0.053 Uiso 1 1 calc R . . . .
C13 C 0.7485(3) 0.7986(3) 0.97458(15) 0.0468(5) Uani 1 1 d . . . . .
H13 H 0.8610 0.8344 0.9348 0.056 Uiso 1 1 calc R . . . .
C9 C 0.1984(3) 0.4919(3) 0.62980(14) 0.0445(5) Uani 1 1 d . . . . .
H9 H 0.1603 0.3688 0.6203 0.053 Uiso 1 1 calc R . . . .
C15 C 0.5816(3) 0.6874(2) 1.13391(15) 0.0488(5) Uani 1 1 d . . . . .
H15 H 0.5822 0.6485 1.2020 0.059 Uiso 1 1 calc R . . . .
C6 C 0.3127(3) 0.8568(3) 0.65947(15) 0.0485(5) Uani 1 1 d . . . . .
H6 H 0.3517 0.9801 0.6686 0.058 Uiso 1 1 calc R . . . .
C3 C 0.2714(3) 0.5149(3) 0.43446(15) 0.0489(5) Uani 1 1 d . . . . .
C5 C 0.3177(3) 0.7772(3) 0.55969(15) 0.0512(5) Uani 1 1 d . . . . .
H5 H 0.3601 0.8477 0.5021 0.061 Uiso 1 1 calc R . . . .
C14 C 0.7482(3) 0.7401(2) 1.07515(16) 0.0499(5) Uani 1 1 d . . . . .
H14 H 0.8610 0.7362 1.1035 0.060 Uiso 1 1 calc R . . . .
C2 C 0.2216(3) 0.2473(3) 0.32734(16) 0.0631(7) Uani 1 1 d . . . . .
H2A H 0.3581 0.2917 0.3074 0.076 Uiso 1 1 calc R . . . .
H2B H 0.1462 0.2687 0.2710 0.076 Uiso 1 1 calc R . . . .
C1 C 0.1348(4) 0.0514(3) 0.3412(2) 0.0821(8) Uani 1 1 d . . . . .
H1A H 0.1451 -0.0128 0.2760 0.123 Uiso 1 1 calc GR . . . .
H1B H -0.0025 0.0076 0.3566 0.123 Uiso 1 1 calc GR . . . .
H1C H 0.2057 0.0329 0.4000 0.123 Uiso 1 1 calc GR . . . .
H1 H 0.298(3) 0.956(3) 0.8532(15) 0.060(6) Uiso 1 1 d . . . . .
H3 H 0.265(4) 0.623(3) 1.220(2) 0.102(9) Uiso 1 1 d . . . . .
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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -2 17 0.2196
0 -1 -17 0.2280
-11 4 1 0.0866
-2 1 17 0.2109
11 -4 0 0.1486
1 -11 0 0.1498
0 9 -10 0.1265
0 2 -17 0.2196
-1 10 4 0.1728
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C16 O3 H3 111.0(16) . .
C3 O1 C2 117.34(16) . .
C7 N1 C10 123.77(17) . .
C7 N1 H1 115.5(12) . .
C10 N1 H1 115.6(13) . .
C11 C12 H12 118.8 . .
C13 C12 H12 118.8 . .
C13 C12 C11 122.36(18) . .
N1 C7 C8 121.94(16) . .
N1 C7 C6 120.23(17) . .
C8 C7 C6 117.80(16) . .
O3 C16 C11 116.56(18) . .
O3 C16 C15 122.65(18) . .
C15 C16 C11 120.79(17) . .
C12 C11 C16 117.39(18) . .
C12 C11 C10 123.48(17) . .
C16 C11 C10 119.13(16) . .
N1 C10 C11 115.25(15) . .
N1 C10 H10A 108.5 . .
N1 C10 H10B 108.5 . .
C11 C10 H10A 108.5 . .
C11 C10 H10B 108.5 . .
H10A C10 H10B 107.5 . .
C9 C4 C3 122.75(18) . .
C9 C4 C5 117.84(16) . .
C5 C4 C3 119.40(17) . .
C7 C8 H8 119.6 . .
C9 C8 C7 120.87(17) . .
C9 C8 H8 119.6 . .
C12 C13 H13 120.4 . .
C12 C13 C14 119.17(18) . .
C14 C13 H13 120.4 . .
C4 C9 H9 119.4 . .
C8 C9 C4 121.22(18) . .
C8 C9 H9 119.4 . .
C16 C15 H15 120.0 . .
C14 C15 C16 120.02(19) . .
C14 C15 H15 120.0 . .
C7 C6 H6 119.6 . .
C5 C6 C7 120.76(19) . .
C5 C6 H6 119.6 . .
O1 C3 C4 112.78(17) . .
O2 C3 O1 122.77(18) . .
O2 C3 C4 124.5(2) . .
C4 C5 H5 119.2 . .
C6 C5 C4 121.51(18) . .
C6 C5 H5 119.2 . .
C13 C14 C15 120.3(2) . .
C13 C14 H14 119.9 . .
C15 C14 H14 119.9 . .
O1 C2 H2A 110.3 . .
O1 C2 H2B 110.3 . .
O1 C2 C1 106.90(18) . .
H2A C2 H2B 108.6 . .
C1 C2 H2A 110.3 . .
C1 C2 H2B 110.3 . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1B 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 C16 1.371(2) .
O3 H3 0.96(3) .
O1 C3 1.333(2) .
O1 C2 1.449(2) .
N1 C7 1.378(2) .
N1 C10 1.443(2) .
N1 H1 0.89(2) .
O2 C3 1.211(2) .
C12 H12 0.9300 .
C12 C11 1.386(2) .
C12 C13 1.375(3) .
C7 C8 1.396(2) .
C7 C6 1.396(2) .
C16 C11 1.393(3) .
C16 C15 1.385(3) .
C11 C10 1.512(3) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C4 C9 1.385(2) .
C4 C3 1.466(2) .
C4 C5 1.391(3) .
C8 H8 0.9300 .
C8 C9 1.377(2) .
C13 H13 0.9300 .
C13 C14 1.376(3) .
C9 H9 0.9300 .
C15 H15 0.9300 .
C15 C14 1.377(3) .
C6 H6 0.9300 .
C6 C5 1.370(3) .
C5 H5 0.9300 .
C14 H14 0.9300 .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C2 C1 1.487(3) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O3 C16 C11 C12 179.24(14) . . . .
O3 C16 C11 C10 0.0(2) . . . .
O3 C16 C15 C14 -179.75(16) . . . .
N1 C7 C8 C9 178.52(18) . . . .
N1 C7 C6 C5 -178.20(18) . . . .
C12 C11 C10 N1 -6.5(2) . . . .
C12 C13 C14 C15 -0.1(3) . . . .
C7 N1 C10 C11 73.7(2) . . . .
C7 C8 C9 C4 -0.6(3) . . . .
C7 C6 C5 C4 -0.1(3) . . . .
C16 C11 C10 N1 172.76(15) . . . .
C16 C15 C14 C13 0.3(3) . . . .
C11 C12 C13 C14 -0.4(3) . . . .
C11 C16 C15 C14 0.1(3) . . . .
C10 N1 C7 C8 17.3(3) . . . .
C10 N1 C7 C6 -164.82(17) . . . .
C8 C7 C6 C5 -0.2(3) . . . .
C13 C12 C11 C16 0.8(3) . . . .
C13 C12 C11 C10 -179.98(17) . . . .
C9 C4 C3 O1 0.6(3) . . . .
C9 C4 C3 O2 -179.2(2) . . . .
C9 C4 C5 C6 0.1(3) . . . .
C15 C16 C11 C12 -0.6(3) . . . .
C15 C16 C11 C10 -179.86(16) . . . .
C6 C7 C8 C9 0.6(3) . . . .
C3 O1 C2 C1 -175.65(18) . . . .
C3 C4 C9 C8 179.58(18) . . . .
C3 C4 C5 C6 -179.25(19) . . . .
C5 C4 C9 C8 0.3(3) . . . .
C5 C4 C3 O1 179.85(16) . . . .
C5 C4 C3 O2 0.1(3) . . . .
C2 O1 C3 O2 1.1(3) . . . .
C2 O1 C3 C4 -178.66(17) . . . .
