#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:58:17 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180458 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/27/7212771.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_7212771
loop_
_publ_author_name
'Kinuta, Takafumi'
'Sato, Tomohiro'
'Tajima, Nobuo'
'Kuroda, Reiko'
'Matsubara, Yoshio'
'Imai, Yoshitane'
_publ_section_title
;
 Chiral crystallization of ether- and imide-bridged biphenyl compounds
 without any outside chiral source
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              3483
_journal_paper_doi               10.1039/c0ce00055h
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C19 H12 N2 O2'
_chemical_formula_weight         300.31
_chemical_name_systematic
;
?
;
_space_group_IT_number           20
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 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                   3.9147(7)
_cell_length_b                   22.823(4)
_cell_length_c                   15.634(3)
_cell_measurement_reflns_used    1727
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      1.78
_cell_volume                     1396.8(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.1122
_diffrn_reflns_av_sigmaI/netI    0.1024
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4688
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.134
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(6)
_refine_ls_extinction_coef       0.0000(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.278
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     69
_refine_ls_number_reflns         1727
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.278
_refine_ls_R_factor_all          0.1492
_refine_ls_R_factor_gt           0.1330
_refine_ls_shift/su_max          1.406
_refine_ls_shift/su_mean         0.032
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0258P)²+17.4718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2422
_refine_ls_wR_factor_ref         0.2483
_reflns_number_gt                1472
_reflns_number_total             1727
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00055h.txt
_cod_data_source_block           31840a-3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1396.9(4)
_cod_database_code               7212771
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
C1 C 0.5496(14) 0.1329(2) 0.2967(3) 0.0051(11) Uiso 1 1 d .
C2 C 0.4984(16) 0.1811(2) 0.3497(3) 0.0064(11) Uani 1 1 d .
C3 C 0.5646(16) 0.1768(3) 0.4383(4) 0.0093(12) Uiso 1 1 d .
H3 H 0.5202 0.2083 0.4744 0.011 Uiso 1 1 calc R
C4 C 0.6963(17) 0.1252(3) 0.4703(4) 0.0117(13) Uiso 1 1 d .
H4 H 0.7455 0.1224 0.5284 0.014 Uiso 1 1 calc R
C5 C 0.7563(17) 0.0777(3) 0.4180(4) 0.0128(13) Uani 1 1 d .
H5 H 0.8489 0.0434 0.4404 0.015 Uiso 1 1 calc R
C6 C 0.6778(16) 0.0815(3) 0.3324(4) 0.0103(12) Uiso 1 1 d .
H6 H 0.7110 0.0489 0.2975 0.012 Uiso 1 1 calc R
C7 C 0.3687(14) 0.2404(2) 0.3253(3) 0.0045(11) Uiso 1 1 d .
O8 O 0.1916(11) 0.26900(16) 0.3718(2) 0.0081(9) Uiso 1 1 d .
N9 N 0.5000 0.2671(3) 0.2500 0.0056(13) Uani 1 2 d S
C10 C 0.5000 0.3318(4) 0.2500 0.0122(18) Uiso 1 2 d S
C11 C 0.3528(16) 0.3616(2) 0.1826(3) 0.0088(12) Uani 1 1 d .
H11 H 0.2522 0.3420 0.1369 0.011 Uiso 1 1 calc R
C12 C 0.3627(16) 0.4227(3) 0.1864(4) 0.0133(13) Uiso 1 1 d .
H12 H 0.2660 0.4432 0.1411 0.016 Uiso 1 1 calc R
N13 N 0.5000 0.4540(3) 0.2500 0.0149(17) Uani 1 2 d S
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C2 0.004(2) 0.008(2) 0.007(2) 0.006(2) -0.002(2) -0.001(2)
C5 0.014(3) 0.010(3) 0.014(3) 0.009(2) 0.000(2) 0.005(2)
N9 0.010(3) 0.000(3) 0.007(3) 0.000 -0.003(3) 0.000
C11 0.014(3) 0.011(3) 0.001(2) -0.002(2) 0.002(2) -0.003(2)
N13 0.026(4) 0.000(3) 0.019(4) 0.000 0.012(4) 0.000
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
C2 C1 C6 118.6(5) . .
C2 C1 C1 122.6(4) . 3_655
C6 C1 C1 118.6(3) . 3_655
C1 C2 C3 120.3(5) . .
C1 C2 C7 127.7(5) . .
C3 C2 C7 112.0(5) . .
C4 C3 C2 118.9(5) . .
C5 C4 C3 121.3(6) . .
C6 C5 C4 119.3(6) . .
C5 C6 C1 121.5(6) . .
O8 C7 N9 118.6(5) . .
O8 C7 C2 122.3(5) . .
N9 C7 C2 118.5(5) . .
C7 N9 C7 129.2(6) 3_655 .
C7 N9 C10 115.4(3) 3_655 .
C7 N9 C10 115.4(3) . .
C11 C10 C11 120.9(8) 3_655 .
C11 C10 N9 119.5(4) 3_655 .
C11 C10 N9 119.5(4) . .
C10 C11 C12 116.6(6) . .
N13 C12 C11 125.3(6) . .
C12 N13 C12 115.3(7) . 3_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.391(8) .
C1 C6 1.394(8) .
C1 C1 1.510(10) 3_655
C2 C3 1.411(8) .
C2 C7 1.496(7) .
C3 C4 1.380(8) .
C4 C5 1.378(8) .
C5 C6 1.377(8) .
C7 O8 1.199(6) .
C7 N9 1.421(6) .
N9 C7 1.421(6) 3_655
N9 C10 1.477(10) .
C10 C11 1.381(7) 3_655
C10 C11 1.381(7) .
C11 C12 1.394(8) .
C12 N13 1.337(7) .
N13 C12 1.337(7) 3_655
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_4
C6 C1 C2 C3 -2.1(8) . .
C1 C1 C2 C3 173.7(6) 3_655 .
C6 C1 C2 C7 179.1(6) . .
C1 C1 C2 C7 -5.0(10) 3_655 .
C1 C2 C3 C4 3.1(9) . .
C7 C2 C3 C4 -177.9(5) . .
C2 C3 C4 C5 -1.5(10) . .
C3 C4 C5 C6 -1.1(10) . .
C4 C5 C6 C1 2.2(10) . .
C2 C1 C6 C5 -0.6(8) . .
C1 C1 C6 C5 -176.6(7) 3_655 .
C1 C2 C7 O8 145.2(6) . .
C3 C2 C7 O8 -33.7(8) . .
C1 C2 C7 N9 -44.1(8) . .
C3 C2 C7 N9 137.0(5) . .
O8 C7 N9 C7 -160.9(6) . 3_655
C2 C7 N9 C7 28.0(4) . 3_655
O8 C7 N9 C10 19.1(6) . .
C2 C7 N9 C10 -152.0(4) . .
C7 N9 C10 C11 -127.8(4) 3_655 3_655
C7 N9 C10 C11 52.2(4) . 3_655
C7 N9 C10 C11 52.2(4) 3_655 .
C7 N9 C10 C11 -127.8(4) . .
C11 C10 C11 C12 0.2(4) 3_655 .
N9 C10 C11 C12 -179.8(4) . .
C10 C11 C12 N13 -0.5(9) . .
C11 C12 N13 C12 0.3(5) . 3_655
