#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/79/2227991.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_2227991
loop_
_publ_author_name
'Wang, Li-Ying'
'Xie, Yong-Sheng'
'Wu, Ren-Min'
'Zuo, Hua'
_publ_section_title
;
 4-(o-Tolylamino)benzaldehyde
;
_journal_coeditor_code           SI2297
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2827
_journal_paper_doi               10.1107/S1600536810040626
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H13 N O'
_chemical_formula_moiety         'C14 H13 N O'
_chemical_formula_sum            'C14 H13 N O'
_chemical_formula_weight         211.25
_chemical_name_systematic
;
4-(o-Tolylamino)benzaldehyde
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 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                   14.193(10)
_cell_length_b                   10.699(10)
_cell_length_c                   7.677(6)
_cell_measurement_reflns_used    2572
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.61
_cell_measurement_theta_min      2.38
_cell_volume                     1165.8(16)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_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      273(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6127
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.209
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         1397
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0500
_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)+(0.1027P)²+0.0736P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1468
_refine_ls_wR_factor_ref         0.1570
_reflns_number_gt                1140
_reflns_number_total             1397
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            si2297.cif
_cod_data_source_block           I
_cod_original_cell_volume        1165.9(16)
_cod_database_code               2227991
_cod_database_fobs_code          2227991
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
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
C C6 1.07328(19) 0.7362(2) 0.3779(5) 0.0546(7) Uani d . 1 . .
H H6 1.0775 0.8092 0.4432 0.066 Uiso calc R 1 . .
C C5 0.99125(16) 0.7114(2) 0.2798(4) 0.0476(6) Uani d . 1 . .
N N1 0.91447(16) 0.7907(2) 0.2760(4) 0.0567(7) Uani d . 1 . .
C C8 0.91320(18) 0.9212(2) 0.3158(4) 0.0496(7) Uani d . 1 . .
C C4 0.98692(19) 0.5966(2) 0.1871(5) 0.0534(7) Uani d . 1 . .
H H4 0.9324 0.5758 0.1265 0.064 Uiso calc R 1 . .
C C3 1.0628(2) 0.5154(2) 0.1858(5) 0.0548(7) Uani d . 1 . .
H H3 1.0591 0.4418 0.1217 0.066 Uiso calc R 1 . .
C C2 1.14506(19) 0.5424(2) 0.2797(5) 0.0531(7) Uani d . 1 . .
C C13 0.83034(19) 0.9730(2) 0.3886(5) 0.0557(7) Uani d . 1 . .
O O1 1.23816(19) 0.36802(18) 0.1876(6) 0.0897(10) Uani d . 1 . .
C C1 1.2296(2) 0.4612(3) 0.2747(6) 0.0660(9) Uani d . 1 . .
C C7 1.1475(2) 0.6520(2) 0.3770(5) 0.0581(8) Uani d . 1 . .
H H7 1.2006 0.6694 0.4437 0.070 Uiso calc R 1 . .
C C9 0.9897(2) 0.9981(3) 0.2718(5) 0.0577(7) Uani d . 1 . .
H H9 1.0431 0.9638 0.2204 0.069 Uiso calc R 1 . .
C C14 0.7450(3) 0.8922(3) 0.4262(8) 0.0821(11) Uani d . 1 . .
H H14A 0.7589 0.8069 0.3968 0.123 Uiso calc R 1 . .
H H14B 0.6926 0.9208 0.3580 0.123 Uiso calc R 1 . .
H H14C 0.7295 0.8976 0.5477 0.123 Uiso calc R 1 . .
C C12 0.8298(3) 1.1013(3) 0.4195(6) 0.0742(10) Uani d . 1 . .
H H12 0.7765 1.1371 0.4693 0.089 Uiso calc R 1 . .
C C10 0.9854(2) 1.1256(3) 0.3053(7) 0.0728(11) Uani d . 1 . .
H H10 1.0365 1.1764 0.2781 0.087 Uiso calc R 1 . .
C C11 0.9052(3) 1.1773(3) 0.3790(7) 0.0814(12) Uani d . 1 . .
H H11 0.9023 1.2627 0.4011 0.098 Uiso calc R 1 . .
H H1A 1.286(2) 0.483(3) 0.339(5) 0.063(9) Uiso d . 1 . .
H H1 0.869(3) 0.755(3) 0.244(5) 0.070(11) Uiso d . 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'
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
C7 C6 C5 . . 120.1(2) ?
C7 C6 H6 . . 119.9 ?
C5 C6 H6 . . 119.9 ?
N1 C5 C6 . . 123.1(2) ?
N1 C5 C4 . . 119.1(2) ?
C6 C5 C4 . . 117.7(2) ?
C5 N1 C8 . . 127.2(2) ?
C5 N1 H1 . . 111(2) ?
C8 N1 H1 . . 122(2) ?
C9 C8 C13 . . 120.6(2) ?
C9 C8 N1 . . 120.7(2) ?
C13 C8 N1 . . 118.5(2) ?
C3 C4 C5 . . 120.8(3) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
C4 C3 C2 . . 121.0(3) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C7 C2 C3 . . 118.0(2) ?
C7 C2 C1 . . 119.3(3) ?
C3 C2 C1 . . 122.7(3) ?
C12 C13 C8 . . 117.3(3) ?
C12 C13 C14 . . 121.7(3) ?
C8 C13 C14 . . 121.1(2) ?
O1 C1 C2 . . 125.5(4) ?
O1 C1 H1A . . 113.4(19) ?
C2 C1 H1A . . 121.0(19) ?
C6 C7 C2 . . 122.2(3) ?
C6 C7 H7 . . 118.9 ?
C2 C7 H7 . . 118.9 ?
C10 C9 C8 . . 119.8(3) ?
C10 C9 H9 . . 120.1 ?
C8 C9 H9 . . 120.1 ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C11 C12 C13 . . 122.5(3) ?
C11 C12 H12 . . 118.7 ?
C13 C12 H12 . . 118.7 ?
C11 C10 C9 . . 120.2(3) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C12 C11 C10 . . 119.6(3) ?
C12 C11 H11 . . 120.2 ?
C10 C11 H11 . . 120.2 ?
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
C6 C7 . 1.386(4) ?
C6 C5 . 1.412(4) ?
C6 H6 . 0.9300 ?
C5 N1 . 1.381(3) ?
C5 C4 . 1.421(4) ?
N1 C8 . 1.429(4) ?
N1 H1 . 0.80(4) ?
C8 C9 . 1.403(4) ?
C8 C13 . 1.415(4) ?
C4 C3 . 1.383(4) ?
C4 H4 . 0.9300 ?
C3 C2 . 1.403(4) ?
C3 H3 . 0.9300 ?
C2 C7 . 1.391(4) ?
C2 C1 . 1.481(4) ?
C13 C12 . 1.393(4) ?
C13 C14 . 1.516(5) ?
O1 C1 . 1.207(5) ?
C1 H1A . 0.97(4) ?
C7 H7 . 0.9300 ?
C9 C10 . 1.390(5) ?
C9 H9 . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C12 C11 . 1.381(6) ?
C12 H12 . 0.9300 ?
C10 C11 . 1.386(6) ?
C10 H10 . 0.9300 ?
C11 H11 . 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
C14 H14A N1 1 0.96 2.40 2.880(6) 110
N1 H1 O1 3_465 0.79(4) 2.32(4) 3.099(5) 171(3)
C14 H14A O1 3_465 0.96 2.48 3.334(6) 148
C9 H9 Cg1 2_774 0.93 2.95 3.603(5) 128
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656304
