#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/81/2228170.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_2228170
loop_
_publ_author_name
'Tian, Xiao'
'Xie, Yong-Sheng'
'Zuo, Hua'
_publ_section_title
;
 4-(p-Tolylamino)benzaldehyde
;
_journal_coeditor_code           ZL2311
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2828
_journal_paper_doi               10.1107/S1600536810040389
_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-(p-Tolylamino)benzaldehyde
;
_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                   5.8356(12)
_cell_length_b                   8.2581(18)
_cell_length_c                   24.137(5)
_cell_measurement_reflns_used    3865
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.04
_cell_measurement_theta_min      2.61
_cell_volume                     1163.2(4)
_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  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART 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  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            6780
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.162
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         1555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0375
_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)+(0.0662P)²+0.0847P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1099
_reflns_number_gt                1414
_reflns_number_total             1555
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            zl2311.cif
_cod_data_source_block           I
_cod_database_code               2228170
_cod_database_fobs_code          2228170
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
C C13 1.3763(3) 0.6409(2) 0.06501(7) 0.0509(4) Uani d . 1 . .
H H13 1.4615 0.5491 0.0564 0.061 Uiso calc R 1 . .
C C11 1.3240(3) 0.9306(2) 0.05882(6) 0.0506(4) Uani d . 1 . .
C C8 1.1747(3) 0.6263(2) 0.09648(6) 0.0490(4) Uani d . 1 . .
C C12 1.4480(3) 0.7908(2) 0.04698(6) 0.0502(4) Uani d . 1 . .
H H12 1.5823 0.7988 0.0264 0.060 Uiso calc R 1 . .
C C5 0.9454(3) 0.4459(2) 0.15636(7) 0.0537(4) Uani d . 1 . .
C C10 1.1209(3) 0.9158(2) 0.08968(7) 0.0536(4) Uani d . 1 . .
H H10 1.0348 1.0077 0.0976 0.064 Uiso calc R 1 . .
N N1 1.1016(3) 0.4765(2) 0.11257(7) 0.0638(5) Uani d . 1 . .
C C9 1.0479(3) 0.7677(2) 0.10832(7) 0.0530(4) Uani d . 1 . .
H H9 0.9137 0.7603 0.1289 0.064 Uiso calc R 1 . .
C C3 0.8304(3) 0.4783(2) 0.25130(7) 0.0588(5) Uani d . 1 . .
H H3 0.8561 0.5239 0.2860 0.071 Uiso calc R 1 . .
C C2 0.6412(3) 0.3791(2) 0.24364(8) 0.0568(4) Uani d . 1 . .
C C14 1.4066(4) 1.0868(2) 0.03930(8) 0.0650(5) Uani d . 1 . .
C C6 0.7577(4) 0.3455(3) 0.14822(9) 0.0667(5) Uani d . 1 . .
H H6 0.7321 0.2995 0.1136 0.080 Uiso calc R 1 . .
C C7 0.6087(4) 0.3136(3) 0.19139(9) 0.0682(5) Uani d . 1 . .
H H7 0.4834 0.2464 0.1852 0.082 Uiso calc R 1 . .
C C4 0.9812(3) 0.5110(2) 0.20869(8) 0.0587(5) Uani d . 1 . .
H H4 1.1076 0.5770 0.2151 0.070 Uiso calc R 1 . .
C C1 0.4755(4) 0.3446(3) 0.29038(9) 0.0733(6) Uani d . 1 . .
H H1A 0.5256 0.3995 0.3233 0.110 Uiso calc R 1 . .
H H1B 0.4702 0.2301 0.2972 0.110 Uiso calc R 1 . .
H H1C 0.3255 0.3823 0.2803 0.110 Uiso calc R 1 . .
O O2 1.3205(4) 1.21695(17) 0.04864(7) 0.0910(6) Uani d . 1 . .
H H1 1.162(5) 0.393(3) 0.0987(10) 0.076(7) Uiso d . 1 . .
H H14 1.551(5) 1.074(3) 0.0161(11) 0.087(7) 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
C12 C13 C8 . . 120.13(16) ?
C12 C13 H13 . . 119.9 ?
C8 C13 H13 . . 119.9 ?
C12 C11 C10 . . 118.36(16) ?
C12 C11 C14 . . 119.75(17) ?
C10 C11 C14 . . 121.89(17) ?
N1 C8 C13 . . 119.53(16) ?
N1 C8 C9 . . 121.91(16) ?
C13 C8 C9 . . 118.50(16) ?
C13 C12 C11 . . 121.52(16) ?
C13 C12 H12 . . 119.2 ?
C11 C12 H12 . . 119.2 ?
C6 C5 C4 . . 118.60(16) ?
C6 C5 N1 . . 120.55(17) ?
C4 C5 N1 . . 120.81(17) ?
C9 C10 C11 . . 120.89(16) ?
C9 C10 H10 . . 119.6 ?
C11 C10 H10 . . 119.6 ?
C8 N1 C5 . . 125.06(16) ?
C8 N1 H1 . . 119.7(17) ?
C5 N1 H1 . . 114.8(17) ?
C10 C9 C8 . . 120.59(16) ?
C10 C9 H9 . . 119.7 ?
C8 C9 H9 . . 119.7 ?
C4 C3 C2 . . 121.58(17) ?
C4 C3 H3 . . 119.2 ?
C2 C3 H3 . . 119.2 ?
C7 C2 C3 . . 117.45(17) ?
C7 C2 C1 . . 121.18(18) ?
C3 C2 C1 . . 121.36(18) ?
O2 C14 C11 . . 126.2(2) ?
O2 C14 H14 . . 122.7(14) ?
C11 C14 H14 . . 111.1(14) ?
C7 C6 C5 . . 120.24(19) ?
C7 C6 H6 . . 119.9 ?
C5 C6 H6 . . 119.9 ?
C6 C7 C2 . . 121.70(19) ?
C6 C7 H7 . . 119.1 ?
C2 C7 H7 . . 119.1 ?
C3 C4 C5 . . 120.41(17) ?
C3 C4 H4 . . 119.8 ?
C5 C4 H4 . . 119.8 ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C13 C12 . 1.377(3) ?
C13 C8 . 1.406(3) ?
C13 H13 . 0.9300 ?
C11 C12 . 1.392(2) ?
C11 C10 . 1.405(3) ?
C11 C14 . 1.455(3) ?
C8 N1 . 1.365(2) ?
C8 C9 . 1.411(2) ?
C12 H12 . 0.9300 ?
C5 C6 . 1.388(3) ?
C5 C4 . 1.388(3) ?
C5 N1 . 1.419(2) ?
C10 C9 . 1.371(2) ?
C10 H10 . 0.9300 ?
N1 H1 . 0.84(2) ?
C9 H9 . 0.9300 ?
C3 C4 . 1.380(3) ?
C3 C2 . 1.387(3) ?
C3 H3 . 0.9300 ?
C2 C7 . 1.385(3) ?
C2 C1 . 1.513(3) ?
C14 O2 . 1.208(3) ?
C14 H14 . 1.02(3) ?
C6 C7 . 1.383(3) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C4 H4 . 0.9300 ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
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
N1 H1 O2 1_545 0.84(3) 2.11(3) 2.934(2) 167(2)
C1 H1A Cg1 3_745 0.96 2.91 3.613(2) 131
C12 H12 Cg1 4_565 0.93 2.77 3.527(2) 140
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656326
