#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/87/2218757.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_2218757
loop_
_publ_author_name
'Qu, Yuan'
'Zhang, Shi-lei'
'Teng, Lei'
'Xia, Xian-you'
'Zhang, Yong'
_publ_section_title
;
 2-(4-Aminophenyl)-1,3-benzoxazole
;
_journal_coeditor_code           LH2630
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1210
_journal_paper_doi               10.1107/S160053680801653X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C13 H10 N2 O'
_chemical_formula_moiety         'C13 H10 N2 O'
_chemical_formula_sum            'C13 H10 N2 O'
_chemical_formula_weight         210.23
_chemical_name_systematic
;
2-(4-Aminophenyl)-1,3-benzoxazole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 95.2430(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.1461(3)
_cell_length_b                   19.5420(12)
_cell_length_c                   12.7705(8)
_cell_measurement_reflns_used    1089
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.60
_cell_measurement_theta_min      2.63
_cell_volume                     1030.38(12)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω 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  0.0862
_diffrn_reflns_av_sigmaI/netI    0.0777
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4628
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_correction_T_min  0.9740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.220
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1902
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.1020
_refine_ls_R_factor_gt           0.0648
_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)+(0.0636P)²+0.0374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1514
_reflns_number_gt                1315
_reflns_number_total             1902
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2630.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2218757
_cod_database_fobs_code          2218757
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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
O O1 1.1291(4) 0.93054(9) 0.09030(12) 0.0548(5) Uani d . 1
N N1 1.0571(5) 0.89549(10) 0.25399(15) 0.0508(6) Uani d . 1
C C8 0.8394(6) 0.82440(13) 0.10509(18) 0.0471(6) Uani d . 1
C C7 1.0044(6) 0.88277(13) 0.15444(18) 0.0472(6) Uani d . 1
C C13 0.6743(6) 0.77900(13) 0.16499(19) 0.0522(7) Uani d . 1
H H13 0.6617 0.7882 0.2360 0.063 Uiso calc R 1
C C11 0.5492(6) 0.70536(14) 0.01598(19) 0.0511(7) Uani d . 1
C C1 1.2748(6) 0.97814(13) 0.15893(18) 0.0488(7) Uani d . 1
N N2 0.4179(7) 0.64627(14) -0.02632(19) 0.0746(8) Uani d D 1
H H2B 0.430(7) 0.6376(13) -0.0924(9) 0.0900(10) Uiso d D 1
H H2A 0.300(6) 0.6220(12) 0.0115(19) 0.0900(10) Uiso d D 1
C C6 1.2309(6) 0.95673(13) 0.25916(18) 0.0487(7) Uani d . 1
C C12 0.5301(6) 0.72124(13) 0.1221(2) 0.0561(7) Uani d . 1
H H12 0.4183 0.6923 0.1638 0.067 Uiso calc R 1
C C9 0.8540(6) 0.80871(14) -0.00072(18) 0.0529(7) Uani d . 1
H H9 0.9622 0.8382 -0.0428 0.064 Uiso calc R 1
C C2 1.4362(7) 1.03717(14) 0.1363(2) 0.0630(8) Uani d . 1
H H2 1.4620 1.0504 0.0676 0.076 Uiso calc R 1
C C5 1.3567(7) 0.99539(15) 0.3444(2) 0.0615(8) Uani d . 1
H H5 1.3315 0.9819 0.4130 0.074 Uiso calc R 1
C C10 0.7122(6) 0.75067(14) -0.04423(19) 0.0556(7) Uani d . 1
H H10 0.7254 0.7415 -0.1152 0.067 Uiso calc R 1
C C3 1.5567(7) 1.07529(15) 0.2214(2) 0.0664(8) Uani d . 1
H H3 1.6650 1.1159 0.2103 0.080 Uiso calc R 1
C C4 1.5205(7) 1.05458(16) 0.3237(2) 0.0640(8) Uani d . 1
H H4 1.6088 1.0812 0.3795 0.077 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 0.0016 '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
C7 O1 C1 104.26(18)
C7 N1 C6 104.6(2)
C13 C8 C9 117.4(2)
C13 C8 C7 120.0(2)
C9 C8 C7 122.4(2)
N1 C7 O1 114.6(2)
N1 C7 C8 127.7(2)
O1 C7 C8 117.7(2)
C12 C13 C8 121.7(2)
C12 C13 H13 119.2
C8 C13 H13 119.2
N2 C11 C10 121.1(2)
N2 C11 C12 121.0(2)
C10 C11 C12 117.9(2)
C6 C1 C2 123.9(2)
C6 C1 O1 107.4(2)
C2 C1 O1 128.7(2)
C11 N2 H2B 119.6(19)
C11 N2 H2A 118(2)
H2B N2 H2A 122(3)
C1 C6 C5 119.5(3)
C1 C6 N1 109.2(2)
C5 C6 N1 131.3(2)
C13 C12 C11 120.6(2)
C13 C12 H12 119.7
C11 C12 H12 119.7
C10 C9 C8 121.4(2)
C10 C9 H9 119.3
C8 C9 H9 119.3
C3 C2 C1 115.9(3)
C3 C2 H2 122.0
C1 C2 H2 122.0
C4 C5 C6 117.5(2)
C4 C5 H5 121.2
C6 C5 H5 121.2
C9 C10 C11 121.0(2)
C9 C10 H10 119.5
C11 C10 H10 119.5
C2 C3 C4 121.6(3)
C2 C3 H3 119.2
C4 C3 H3 119.2
C5 C4 C3 121.5(3)
C5 C4 H4 119.3
C3 C4 H4 119.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.374(3)
O1 C1 1.379(3)
N1 C7 1.294(3)
N1 C6 1.395(3)
C8 C13 1.392(3)
C8 C9 1.392(3)
C8 C7 1.445(4)
C13 C12 1.368(3)
C13 H13 0.9300
C11 N2 1.367(4)
C11 C10 1.388(3)
C11 C12 1.399(3)
C1 C6 1.374(3)
C1 C2 1.378(4)
N2 H2B 0.868(10)
N2 H2A 0.859(10)
C6 C5 1.387(3)
C12 H12 0.9300
C9 C10 1.372(3)
C9 H9 0.9300
C2 C3 1.373(4)
C2 H2 0.9300
C5 C4 1.379(4)
C5 H5 0.9300
C10 H10 0.9300
C3 C4 1.389(4)
C3 H3 0.9300
C4 H4 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
N2 H2B N1 4_575 0.868(10) 2.174(12) 3.028(3) 168(3)
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
C6 N1 C7 O1 0.1(3)
C6 N1 C7 C8 178.5(2)
C1 O1 C7 N1 -0.1(3)
C1 O1 C7 C8 -178.7(2)
C13 C8 C7 N1 9.5(4)
C9 C8 C7 N1 -166.4(2)
C13 C8 C7 O1 -172.1(2)
C9 C8 C7 O1 12.0(3)
C9 C8 C13 C12 -0.3(4)
C7 C8 C13 C12 -176.4(2)
C7 O1 C1 C6 0.1(2)
C7 O1 C1 C2 -179.6(2)
C2 C1 C6 C5 -0.7(4)
O1 C1 C6 C5 179.6(2)
C2 C1 C6 N1 179.7(2)
O1 C1 C6 N1 0.0(3)
C7 N1 C6 C1 -0.1(3)
C7 N1 C6 C5 -179.6(3)
C8 C13 C12 C11 1.1(4)
N2 C11 C12 C13 177.1(3)
C10 C11 C12 C13 -1.4(4)
C13 C8 C9 C10 -0.2(4)
C7 C8 C9 C10 175.9(2)
C6 C1 C2 C3 0.1(4)
O1 C1 C2 C3 179.7(2)
C1 C6 C5 C4 0.4(4)
N1 C6 C5 C4 179.9(2)
C8 C9 C10 C11 -0.1(4)
N2 C11 C10 C9 -177.6(3)
C12 C11 C10 C9 0.9(4)
C1 C2 C3 C4 0.9(4)
C6 C5 C4 C3 0.5(4)
C2 C3 C4 C5 -1.2(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 80067
