#------------------------------------------------------------------------------
#$Date: 2019-11-28 19:30:57 +0100 (jue 28 de nov de 2019) $
#$Revision: 244535 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/90/7239072.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_7239072
loop_
_publ_author_name
'Li, Nai-Kai'
'Liu, Zhao-Min'
'Huang, Xiao-Fei'
'Zhang, Jin-Xin'
'Chen, Xiang'
'Wang, Yong'
'Wang, Xing-Wang'
_publ_section_title
;
 Enantioselective Strecker-type reaction between azomethine imines and
 trimethylsilyl cyanide catalyzed by a cinchona alkaloid-derived thiourea
 bearing multiple hydrogen-bonding donors
;
_journal_issue                   24
_journal_name_full               'RSC Advances'
_journal_page_first              9154
_journal_paper_doi               10.1039/c3ra41640b
_journal_volume                  3
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C11 H10 Br N3 O'
_chemical_formula_weight         280.13
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_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                   5.6282(9)
_cell_length_b                   9.0457(14)
_cell_length_c                   22.768(4)
_cell_measurement_reflns_used    2087
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      43.706
_cell_measurement_theta_min      4.845
_cell_volume                     1159.1(3)
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0534
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            6749
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    3.528
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42118
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.276
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.143
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.008(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2154
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0462
_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)+(0.0648P)²+0.3193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1220
_reflns_number_gt                1804
_reflns_number_total             2154
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra41640b.txt
_cod_data_source_block           cd212477
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/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_original_cell_volume        1159.2(3)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7239072
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_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
Br1 Br -0.34735(14) 1.41914(7) 0.88430(3) 0.0927(3) Uani 1 1 d .
N1 N 0.3261(6) 0.8464(4) 0.77585(15) 0.0374(7) Uani 1 1 d D
N2 N 0.1313(5) 0.9013(3) 0.80990(13) 0.0327(7) Uani 1 1 d .
N3 N 0.4310(9) 0.7416(5) 0.9250(2) 0.0668(12) Uani 1 1 d .
O1 O 0.4860(6) 0.6346(3) 0.74116(15) 0.0531(8) Uani 1 1 d .
C1 C 0.3347(8) 0.7011(4) 0.76897(18) 0.0387(9) Uani 1 1 d .
C2 C 0.1194(8) 0.6368(5) 0.7988(2) 0.0452(10) Uani 1 1 d .
H2A H 0.1638 0.5830 0.8340 0.054 Uiso 1 1 calc R
H2B H 0.0340 0.5708 0.7727 0.054 Uiso 1 1 calc R
C3 C -0.0289(7) 0.7712(5) 0.8138(2) 0.0427(10) Uani 1 1 d .
H3A H -0.1596 0.7812 0.7863 0.051 Uiso 1 1 calc R
H3B H -0.0935 0.7623 0.8531 0.051 Uiso 1 1 calc R
C4 C 0.2239(7) 0.9556(4) 0.86668(16) 0.0327(9) Uani 1 1 d .
H4 H 0.3445 1.0308 0.8582 0.039 Uiso 1 1 calc R
C5 C 0.0266(7) 1.0297(4) 0.90075(16) 0.0332(8) Uani 1 1 d .
C6 C -0.0719(9) 0.9675(5) 0.95050(19) 0.0466(11) Uani 1 1 d .
H6 H -0.0126 0.8791 0.9653 0.056 Uiso 1 1 calc R
C7 C -0.2594(9) 1.0378(5) 0.9780(2) 0.0501(11) Uani 1 1 d .
H7 H -0.3279 0.9948 1.0110 0.060 Uiso 1 1 calc R
C8 C -0.3455(9) 1.1685(5) 0.95785(19) 0.0500(11) Uani 1 1 d .
H8 H -0.4728 1.2147 0.9763 0.060 Uiso 1 1 calc R
C9 C -0.2393(9) 1.2311(5) 0.9093(2) 0.0464(11) Uani 1 1 d .
C10 C -0.0552(8) 1.1647(5) 0.88055(19) 0.0430(10) Uani 1 1 d .
H10 H 0.0142 1.2094 0.8480 0.052 Uiso 1 1 calc R
C11 C 0.3408(8) 0.8361(5) 0.90099(17) 0.0413(10) Uani 1 1 d .
H1 H 0.411(6) 0.910(3) 0.7607(16) 0.029(10) Uiso 1 1 d D
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
Br1 0.1179(6) 0.0670(4) 0.0933(5) 0.0179(3) 0.0289(4) 0.0560(4)
N1 0.0393(19) 0.0271(16) 0.0457(19) 0.0011(14) 0.0108(16) 0.0033(16)
N2 0.0308(16) 0.0333(16) 0.0341(17) -0.0013(13) 0.0052(13) 0.0102(15)
N3 0.083(3) 0.047(2) 0.070(3) 0.005(2) -0.026(2) 0.016(2)
O1 0.0513(18) 0.0441(16) 0.064(2) -0.0139(15) 0.0097(16) 0.0131(15)
C1 0.039(2) 0.037(2) 0.040(2) -0.0077(16) -0.0003(19) 0.0043(19)
C2 0.045(2) 0.037(2) 0.054(3) -0.0123(19) 0.000(2) -0.0102(19)
C3 0.032(2) 0.045(2) 0.051(2) -0.014(2) 0.0014(18) -0.0039(19)
C4 0.035(2) 0.0276(17) 0.035(2) -0.0010(15) -0.0022(16) -0.0013(16)
C5 0.036(2) 0.0302(18) 0.033(2) -0.0052(15) -0.0029(17) 0.0000(17)
C6 0.063(3) 0.036(2) 0.041(2) 0.0021(18) 0.006(2) 0.001(2)
C7 0.056(3) 0.049(3) 0.046(3) -0.003(2) 0.014(2) -0.008(2)
C8 0.043(2) 0.061(3) 0.047(3) -0.017(2) 0.011(2) -0.004(2)
C9 0.058(3) 0.038(2) 0.043(2) -0.0024(19) -0.002(2) 0.015(2)
C10 0.053(2) 0.041(2) 0.035(2) -0.0022(18) 0.005(2) 0.0118(19)
C11 0.047(2) 0.039(2) 0.038(2) -0.0027(17) -0.007(2) 0.003(2)
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'
Br Br -0.2901 2.4595 '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
C1 N1 N2 115.9(3)
C1 N1 H1 128(3)
N2 N1 H1 116(3)
N1 N2 C4 108.6(3)
N1 N2 C3 102.8(3)
C4 N2 C3 115.2(3)
O1 C1 N1 125.2(4)
O1 C1 C2 127.3(4)
N1 C1 C2 107.5(4)
C1 C2 C3 103.6(3)
C1 C2 H2A 111.0
C3 C2 H2A 111.0
C1 C2 H2B 111.0
C3 C2 H2B 111.0
H2A C2 H2B 109.0
N2 C3 C2 106.8(3)
N2 C3 H3A 110.4
C2 C3 H3A 110.4
N2 C3 H3B 110.4
C2 C3 H3B 110.4
H3A C3 H3B 108.6
N2 C4 C11 112.0(3)
N2 C4 C5 109.7(3)
C11 C4 C5 112.2(3)
N2 C4 H4 107.6
C11 C4 H4 107.6
C5 C4 H4 107.6
C6 C5 C10 119.9(4)
C6 C5 C4 122.4(4)
C10 C5 C4 117.7(3)
C5 C6 C7 119.4(4)
C5 C6 H6 120.3
C7 C6 H6 120.3
C8 C7 C6 121.3(4)
C8 C7 H7 119.3
C6 C7 H7 119.3
C7 C8 C9 118.3(4)
C7 C8 H8 120.8
C9 C8 H8 120.8
C10 C9 C8 122.2(4)
C10 C9 Br1 119.7(4)
C8 C9 Br1 118.1(3)
C9 C10 C5 118.8(4)
C9 C10 H10 120.6
C5 C10 H10 120.6
N3 C11 C4 177.1(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C9 1.894(4)
N1 C1 1.325(5)
N1 N2 1.432(4)
N1 H1 0.821(19)
N2 C4 1.478(5)
N2 C3 1.485(5)
N3 C11 1.135(5)
O1 C1 1.219(5)
C1 C2 1.507(6)
C2 C3 1.513(6)
C2 H2A 0.9700
C2 H2B 0.9700
C3 H3A 0.9700
C3 H3B 0.9700
C4 C11 1.487(6)
C4 C5 1.511(6)
C4 H4 0.9800
C5 C6 1.381(6)
C5 C10 1.384(6)
C6 C7 1.383(7)
C6 H6 0.9300
C7 C8 1.358(7)
C7 H7 0.9300
C8 C9 1.379(7)
C8 H8 0.9300
C9 C10 1.365(6)
C10 H10 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.821(19) 2.12(3) 2.840(4) 147(4) 3_656
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
C1 N1 N2 C4 109.2(4)
C1 N1 N2 C3 -13.2(5)
N2 N1 C1 O1 179.5(4)
N2 N1 C1 C2 2.3(5)
O1 C1 C2 C3 -167.6(4)
N1 C1 C2 C3 9.5(5)
N1 N2 C3 C2 18.2(4)
C4 N2 C3 C2 -99.7(4)
C1 C2 C3 N2 -17.2(4)
N1 N2 C4 C11 -61.0(4)
C3 N2 C4 C11 53.6(4)
N1 N2 C4 C5 173.7(3)
C3 N2 C4 C5 -71.6(4)
N2 C4 C5 C6 109.1(4)
C11 C4 C5 C6 -16.0(5)
N2 C4 C5 C10 -71.0(4)
C11 C4 C5 C10 163.9(4)
C10 C5 C6 C7 3.1(6)
C4 C5 C6 C7 -177.0(4)
C5 C6 C7 C8 -1.4(7)
C6 C7 C8 C9 -0.7(7)
C7 C8 C9 C10 1.3(7)
C7 C8 C9 Br1 -176.2(4)
C8 C9 C10 C5 0.4(7)
Br1 C9 C10 C5 177.8(3)
C6 C5 C10 C9 -2.6(6)
C4 C5 C10 C9 177.5(4)
N2 C4 C11 N3 20(10)
C5 C4 C11 N3 144(10)
