#------------------------------------------------------------------------------
#$Date: 2019-11-26 08:19:15 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243044 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/32/4133207.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_4133207
loop_
_publ_author_name
'Taniguchi, Tohru'
'Suzuki, Takahiro'
'Satoh, Haruka'
'Shichibu, Yukatsu'
'Konishi, Katsuaki'
'Monde, Kenji'
_publ_section_title
;
 Preparation of Carbodiimides with One-Handed Axial Chirality.
;
_journal_issue                   46
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15577
_journal_page_last               15581
_journal_paper_doi               10.1021/jacs.8b08969
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_sum            'C15 H12 N2'
_chemical_formula_weight         220.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.8881(15)
_cell_length_b                   5.8140(9)
_cell_length_c                   9.7349(15)
_cell_measurement_reflns_used    114
_cell_measurement_temperature    90.(2)
_cell_measurement_theta_max      22.2337
_cell_measurement_theta_min      2.0911
_cell_volume                     559.65(15)
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_data_collection       'Bruker SMART APEXII'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  'Generate Report (Bruker AXS)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      90.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            3270
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.09
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.191
_refine_ls_abs_structure_details
;

Flack x determined using 368 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1296
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0351
_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)+(0.0323P)²+0.0671P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0784
_reflns_number_gt                1075
_reflns_number_total             1296
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b08969_si_001.cif
_cod_data_source_block           exp828
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4133207
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'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_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
C C1 0.1939(2) 0.4857(4) 0.2750(2) 0.0258(5) Uani d . . . 1
C C2 0.1621(2) 0.2990(4) 0.1922(2) 0.0285(5) Uani d . . . 1
C C3 0.2614(2) 0.1921(4) 0.1158(2) 0.0282(5) Uani d . . . 1
C C4 0.3937(2) 0.2723(4) 0.1231(2) 0.0250(5) Uani d . . . 1
C C5 0.42773(19) 0.4595(3) 0.2052(2) 0.0219(4) Uani d . . . 1
C C6 0.3257(2) 0.5692(3) 0.2827(2) 0.0238(5) Uani d . . . 1
C C7 0.3579(2) 0.7633(4) 0.3806(2) 0.0265(5) Uani d . . . 1
C C8 0.5 0.5 0.4870(3) 0.0253(6) Uani d T P S 1
H H1 0.123(2) 0.559(4) 0.329(2) 0.029(6) Uiso d . . . 1
H H2 0.069(2) 0.240(4) 0.190(2) 0.033(6) Uiso d . . . 1
H H3 0.244(2) 0.058(4) 0.058(2) 0.036(7) Uiso d . . . 1
H H4 0.464(2) 0.198(3) 0.068(2) 0.023(5) Uiso d . . . 1
H H5 0.276(2) 0.816(4) 0.429(3) 0.041(7) Uiso d . . . 1
H H6 0.396(2) 0.902(4) 0.331(2) 0.029(6) Uiso d . . . 1
N N1 0.45965(16) 0.6987(3) 0.48654(17) 0.0277(4) Uani 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 C6 . 121.0(2)
C2 C1 H1 . 119.6(13)
C6 C1 H1 . 119.4(13)
C3 C2 C1 . 120.2(2)
C3 C2 H2 . 120.0(13)
C1 C2 H2 . 119.7(13)
C2 C3 C4 . 119.4(2)
C2 C3 H3 . 123.0(13)
C4 C3 H3 . 117.6(13)
C3 C4 C5 . 121.3(2)
C3 C4 H4 . 119.5(11)
C5 C4 H4 . 119.2(11)
C4 C5 C6 . 119.17(18)
C4 C5 C5 2_665 118.31(19)
C6 C5 C5 2_665 122.50(17)
C1 C6 C5 . 118.86(18)
C1 C6 C7 . 119.41(18)
C5 C6 C7 . 121.59(17)
N1 C7 C6 . 112.98(16)
N1 C7 H5 . 107.6(15)
C6 C7 H5 . 111.0(13)
N1 C7 H6 . 106.2(12)
C6 C7 H6 . 111.7(13)
H5 C7 H6 . 107.0(17)
N1 C8 N1 2_665 179.6(3)
C8 N1 C7 . 117.49(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.389(3)
C1 C6 . 1.393(3)
C1 H1 . 0.97(2)
C2 C3 . 1.380(3)
C2 H2 . 0.98(2)
C3 C4 . 1.391(3)
C3 H3 . 0.98(2)
C4 C5 . 1.392(3)
C4 H4 . 0.98(2)
C5 C6 . 1.412(3)
C5 C5 2_665 1.505(4)
C6 C7 . 1.512(3)
C7 N1 . 1.489(3)
C7 H5 . 0.99(2)
C7 H6 . 1.01(2)
C8 N1 . 1.2222(19)
C8 N1 2_665 1.2222(19)
