#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/26/8102640.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_8102640
loop_
_publ_author_name
'Zi-Long Tang'
'Zhong-Hua Zhu'
'Chao-Yi Zhang'
'Wei-Wen Chen'
'Han-Wen Liu'
'Ke-Long Huang'
_publ_section_title
;
 Crystal structure of
 2-(2-nitrophenyl)-3-(p-tolyl)-3,4-dihydro-2H-1,3-benzoxazine,
 C21H18N2O3
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              147
_journal_volume                  225
_journal_year                    2010
_chemical_formula_sum            'C21 H18 N2 O3'
_chemical_formula_weight         346.37
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                66.675(2)
_cell_angle_beta                 81.279(2)
_cell_angle_gamma                73.525(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0481(7)
_cell_length_b                   10.2521(9)
_cell_length_c                   10.7292(9)
_cell_measurement_reflns_used    1580
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     875.53(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  '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  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5940
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9772
_exptl_absorpt_correction_T_min  0.9619
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.145
_refine_ls_extinction_coef       0.111(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3279
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0488
_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)+(0.1265P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1390
_refine_ls_wR_factor_ref         0.1925
_reflns_number_gt                2367
_reflns_number_total             3279
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2884.cff
_cod_data_source_block           zzh2_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8102640
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1736(2) 0.2577(2) 0.2541(2) 0.0451(5) Uani 1 1 d . . .
C2 C -0.3282(3) 0.2710(3) 0.2914(2) 0.0575(6) Uani 1 1 d . . .
H2 H -0.3701 0.1901 0.3211 0.069 Uiso 1 1 calc R . .
C3 C -0.4195(3) 0.4064(3) 0.2838(3) 0.0651(7) Uani 1 1 d . . .
H3 H -0.5244 0.4181 0.3070 0.078 Uiso 1 1 calc R . .
C4 C -0.3554(3) 0.5235(3) 0.2421(2) 0.0584(6) Uani 1 1 d . . .
H4 H -0.4170 0.6146 0.2380 0.070 Uiso 1 1 calc R . .
C5 C -0.1995(2) 0.5078(2) 0.2059(2) 0.0465(5) Uani 1 1 d . . .
H5 H -0.1579 0.5886 0.1783 0.056 Uiso 1 1 calc R . .
C6 C -0.1050(2) 0.3742(2) 0.21026(18) 0.0390(5) Uani 1 1 d . . .
C7 C 0.0656(2) 0.3550(2) 0.16896(18) 0.0375(5) Uani 1 1 d . . .
H7 H 0.0835 0.3226 0.0922 0.045 Uiso 1 1 calc R . .
C8 C 0.1426(2) 0.5317(2) 0.22043(19) 0.0392(5) Uani 1 1 d . . .
C9 C 0.1618(3) 0.6729(2) 0.1782(2) 0.0521(6) Uani 1 1 d . . .
H9 H 0.1491 0.7360 0.0879 0.063 Uiso 1 1 calc R . .
C10 C 0.1997(3) 0.7187(3) 0.2710(3) 0.0612(7) Uani 1 1 d . . .
H10 H 0.2121 0.8133 0.2433 0.073 Uiso 1 1 calc R . .
C11 C 0.2193(3) 0.6252(3) 0.4047(3) 0.0600(6) Uani 1 1 d . . .
H11 H 0.2459 0.6560 0.4670 0.072 Uiso 1 1 calc R . .
C12 C 0.1991(3) 0.4853(3) 0.4452(2) 0.0508(6) Uani 1 1 d . . .
H12 H 0.2110 0.4231 0.5358 0.061 Uiso 1 1 calc R . .
C13 C 0.1617(2) 0.4355(2) 0.35450(18) 0.0397(5) Uani 1 1 d . . .
C14 C 0.1419(2) 0.2828(2) 0.39565(18) 0.0419(5) Uani 1 1 d . . .
H14A H 0.2196 0.2140 0.4593 0.050 Uiso 1 1 calc R . .
H14B H 0.0413 0.2775 0.4410 0.050 Uiso 1 1 calc R . .
C15 C 0.3044(2) 0.1676(2) 0.24131(19) 0.0397(5) Uani 1 1 d . . .
C16 C 0.3838(2) 0.2255(2) 0.1197(2) 0.0487(5) Uani 1 1 d . . .
H16 H 0.3442 0.3204 0.0599 0.058 Uiso 1 1 calc R . .
C17 C 0.5221(3) 0.1421(3) 0.0871(2) 0.0582(6) Uani 1 1 d . . .
H17 H 0.5720 0.1814 0.0035 0.070 Uiso 1 1 calc R . .
C18 C 0.5882(3) 0.0031(3) 0.1739(3) 0.0560(6) Uani 1 1 d . . .
C19 C 0.7392(3) -0.0861(3) 0.1357(4) 0.0820(9) Uani 1 1 d . . .
H19A H 0.7195 -0.1358 0.0830 0.123 Uiso 1 1 calc R . .
H19B H 0.7894 -0.1569 0.2167 0.123 Uiso 1 1 calc R . .
H19C H 0.8045 -0.0223 0.0832 0.123 Uiso 1 1 calc R . .
C20 C 0.5096(3) -0.0514(3) 0.2969(3) 0.0630(7) Uani 1 1 d . . .
H20 H 0.5523 -0.1443 0.3587 0.076 Uiso 1 1 calc R . .
C21 C 0.3705(3) 0.0277(2) 0.3305(2) 0.0557(6) Uani 1 1 d . . .
H21 H 0.3201 -0.0127 0.4136 0.067 Uiso 1 1 calc R . .
N1 N -0.0828(2) 0.1121(2) 0.2583(2) 0.0558(5) Uani 1 1 d . . .
N2 N 0.15581(17) 0.24197(17) 0.27747(15) 0.0397(4) Uani 1 1 d . . .
O1 O -0.0044(2) 0.10369(18) 0.15773(19) 0.0660(5) Uani 1 1 d . . .
O2 O -0.0948(3) 0.0078(2) 0.3608(2) 0.0946(8) Uani 1 1 d . . .
O3 O 0.10520(15) 0.49394(14) 0.12184(13) 0.0430(4) Uani 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_
_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
_geom_angle_publ_flag
C2 C1 C6 123.1(2) . . ?
C2 C1 N1 116.5(2) . . ?
C6 C1 N1 120.43(18) . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 116.62(19) . . ?
C5 C6 C7 122.02(19) . . ?
C1 C6 C7 121.36(17) . . ?
N2 C7 O3 114.19(16) . . ?
N2 C7 C6 110.18(14) . . ?
O3 C7 C6 109.97(15) . . ?
N2 C7 H7 107.4 . . ?
O3 C7 H7 107.4 . . ?
C6 C7 H7 107.4 . . ?
O3 C8 C13 122.69(17) . . ?
O3 C8 C9 116.08(17) . . ?
C13 C8 C9 121.23(19) . . ?
C10 C9 C8 119.5(2) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 120.4(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 119.4(2) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C13 121.7(2) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C12 C13 C8 117.77(19) . . ?
C12 C13 C14 122.69(18) . . ?
C8 C13 C14 119.54(17) . . ?
N2 C14 C13 111.13(15) . . ?
N2 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
N2 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C21 118.26(18) . . ?
C16 C15 N2 123.34(17) . . ?
C21 C15 N2 118.36(17) . . ?
C15 C16 C17 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 122.3(2) . . ?
C18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C17 C18 C20 116.9(2) . . ?
C17 C18 C19 121.3(2) . . ?
C20 C18 C19 121.8(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C18 122.0(2) . . ?
C21 C20 H20 119.0 . . ?
C18 C20 H20 119.0 . . ?
C20 C21 C15 120.5(2) . . ?
C20 C21 H21 119.8 . . ?
C15 C21 H21 119.8 . . ?
O2 N1 O1 124.2(2) . . ?
O2 N1 C1 117.43(19) . . ?
O1 N1 C1 118.30(18) . . ?
C15 N2 C7 117.02(14) . . ?
C15 N2 C14 117.85(15) . . ?
C7 N2 C14 111.64(14) . . ?
C8 O3 C7 115.88(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.379(3) . ?
C1 C6 1.386(3) . ?
C1 N1 1.472(3) . ?
C2 C3 1.377(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.518(3) . ?
C7 N2 1.431(2) . ?
C7 O3 1.441(2) . ?
C7 H7 0.9800 . ?
C8 O3 1.375(2) . ?
C8 C13 1.388(3) . ?
C8 C9 1.389(3) . ?
C9 C10 1.376(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.378(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.505(3) . ?
C14 N2 1.463(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.384(3) . ?
C15 C21 1.389(3) . ?
C15 N2 1.426(2) . ?
C16 C17 1.385(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(4) . ?
C17 H17 0.9300 . ?
C18 C20 1.384(4) . ?
C18 C19 1.513(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.374(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
N1 O2 1.210(2) . ?
N1 O1 1.217(2) . ?
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
_geom_torsion_publ_flag
C6 C1 C2 C3 0.6(3) . . . . ?
N1 C1 C2 C3 -177.4(2) . . . . ?
C1 C2 C3 C4 -1.1(4) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C4 C5 C6 C7 179.02(19) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
N1 C1 C6 C5 178.25(18) . . . . ?
C2 C1 C6 C7 -179.47(19) . . . . ?
N1 C1 C6 C7 -1.6(3) . . . . ?
C5 C6 C7 N2 124.20(19) . . . . ?
C1 C6 C7 N2 -56.0(2) . . . . ?
C5 C6 C7 O3 -2.5(2) . . . . ?
C1 C6 C7 O3 177.32(16) . . . . ?
O3 C8 C9 C10 -179.87(18) . . . . ?
C13 C8 C9 C10 -0.3(3) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C11 C12 C13 C8 -0.9(3) . . . . ?
C11 C12 C13 C14 178.90(18) . . . . ?
O3 C8 C13 C12 -179.88(16) . . . . ?
C9 C8 C13 C12 0.6(3) . . . . ?
O3 C8 C13 C14 0.3(3) . . . . ?
C9 C8 C13 C14 -179.23(17) . . . . ?
C12 C13 C14 N2 -160.43(18) . . . . ?
C8 C13 C14 N2 19.4(2) . . . . ?
C21 C15 C16 C17 2.7(3) . . . . ?
N2 C15 C16 C17 -174.91(19) . . . . ?
C15 C16 C17 C18 -2.3(4) . . . . ?
C16 C17 C18 C20 0.2(4) . . . . ?
C16 C17 C18 C19 179.8(2) . . . . ?
C17 C18 C20 C21 1.3(4) . . . . ?
C19 C18 C20 C21 -178.2(2) . . . . ?
C18 C20 C21 C15 -0.8(4) . . . . ?
C16 C15 C21 C20 -1.2(4) . . . . ?
N2 C15 C21 C20 176.5(2) . . . . ?
C2 C1 N1 O2 -49.6(3) . . . . ?
C6 C1 N1 O2 132.4(2) . . . . ?
C2 C1 N1 O1 128.3(2) . . . . ?
C6 C1 N1 O1 -49.7(3) . . . . ?
C16 C15 N2 C7 21.0(3) . . . . ?
C21 C15 N2 C7 -156.6(2) . . . . ?
C16 C15 N2 C14 -116.5(2) . . . . ?
C21 C15 N2 C14 65.9(2) . . . . ?
O3 C7 N2 C15 -81.40(19) . . . . ?
C6 C7 N2 C15 154.27(16) . . . . ?
O3 C7 N2 C14 58.64(19) . . . . ?
C6 C7 N2 C14 -65.7(2) . . . . ?
C13 C14 N2 C15 92.24(19) . . . . ?
C13 C14 N2 C7 -47.4(2) . . . . ?
C13 C8 O3 C7 8.3(2) . . . . ?
C9 C8 O3 C7 -172.13(15) . . . . ?
N2 C7 O3 C8 -38.0(2) . . . . ?
C6 C7 O3 C8 86.48(18) . . . . ?
