#------------------------------------------------------------------------------
#$Date: 2015-07-05 14:19:19 +0300 (Sun, 05 Jul 2015) $
#$Revision: 140277 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/00/1520068.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_1520068
loop_
_publ_author_name
'Zhu, Xiaxia'
'Du, Haifeng'
_publ_section_title
;
 A Highly Stereoselective Metal-Free Hydrogenation of Diimines for the
 Synthesis of Cis-Vicinal Diamines.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3106
_journal_page_last               3109
_journal_paper_doi               10.1021/acs.orglett.5b01380
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C26 H22 Br2 N2, 2(C3 H7 N O)'
_chemical_formula_sum            'C32 H36 Br2 N4 O2'
_chemical_formula_weight         668.47
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-11-24
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.279(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.037(2)
_cell_length_b                   8.2451(18)
_cell_length_c                   18.991(5)
_cell_measurement_reflns_used    4436
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4832
_cell_measurement_theta_min      2.0689
_cell_volume                     1541.3(6)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution
;
'SHELXS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0981
_diffrn_orient_matrix_UB_12      -0.0196
_diffrn_orient_matrix_UB_13      0.0175
_diffrn_orient_matrix_UB_21      0.0203
_diffrn_orient_matrix_UB_22      0.0050
_diffrn_orient_matrix_UB_23      0.1195
_diffrn_orient_matrix_UB_31      -0.0205
_diffrn_orient_matrix_UB_32      0.0496
_diffrn_orient_matrix_UB_33      0.0014
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_laue_measured_fraction_full 0.988
_diffrn_reflns_laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10413
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_min         2.702
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    2.664
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_description       block
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.787
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0356P)²+1.7513P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3218
_reflns_number_total             3483
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol5b01380_si_002.cif
_cod_data_source_block           sa3728
_cod_depositor_comments          'Adding full bibliography for 1520068.cif.'
_cod_database_code               1520068
_shelxl_version_number           2013-4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_diffrn_number_total             3735
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13),
 C16(H16)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
Br1 Br 1.16406(3) -0.20187(4) 0.76422(2) 0.03671(11) Uani 1 1 d .
N1 N 0.68523(19) 0.0003(3) 0.53271(10) 0.0223(4) Uani 1 1 d .
C1 C 0.5026(2) 0.1002(3) 0.59294(12) 0.0223(5) Uani 1 1 d .
C2 C 0.5338(3) 0.2648(3) 0.59176(13) 0.0280(5) Uani 1 1 d .
H2 H 0.5813 0.3041 0.5579 0.034 Uiso 1 1 calc R
C3 C 0.4941(3) 0.3711(4) 0.64098(15) 0.0340(6) Uani 1 1 d .
H3 H 0.5145 0.4809 0.6395 0.041 Uiso 1 1 calc R
C4 C 0.4245(3) 0.3133(4) 0.69205(14) 0.0349(6) Uani 1 1 d .
H4 H 0.3979 0.3842 0.7248 0.042 Uiso 1 1 calc R
C5 C 0.3949(3) 0.1502(4) 0.69399(13) 0.0329(6) Uani 1 1 d .
H5 H 0.3492 0.1111 0.7286 0.040 Uiso 1 1 calc R
C6 C 0.4329(2) 0.0437(3) 0.64459(12) 0.0265(5) Uani 1 1 d .
H6 H 0.4116 -0.0659 0.6461 0.032 Uiso 1 1 calc R
C7 C 0.5432(2) -0.0149(3) 0.53803(11) 0.0209(5) Uani 1 1 d .
H7 H 0.5273 -0.1263 0.5523 0.025 Uiso 1 1 calc R
C8 C 0.7898(2) -0.0441(3) 0.58773(11) 0.0194(4) Uani 1 1 d .
C9 C 0.7728(2) -0.1471(3) 0.64387(13) 0.0258(5) Uani 1 1 d .
H9 H 0.6864 -0.1837 0.6467 0.031 Uiso 1 1 calc R
C10 C 0.8841(3) -0.1955(3) 0.69566(13) 0.0284(5) Uani 1 1 d .
H10 H 0.8719 -0.2653 0.7323 0.034 Uiso 1 1 calc R
C11 C 1.0122(2) -0.1397(3) 0.69241(13) 0.0258(5) Uani 1 1 d .
C12 C 1.0319(2) -0.0386(3) 0.63709(13) 0.0265(5) Uani 1 1 d .
H12 H 1.1187 -0.0024 0.6348 0.032 Uiso 1 1 calc R
C13 C 0.9218(2) 0.0081(3) 0.58541(12) 0.0241(5) Uani 1 1 d .
H13 H 0.9355 0.0757 0.5483 0.029 Uiso 1 1 calc R
O1 O 0.7183(3) 0.3073(3) 0.45980(15) 0.0577(7) Uani 1 1 d .
N2 N 0.8443(3) 0.5205(3) 0.43450(14) 0.0396(6) Uani 1 1 d .
C14 C 0.9276(4) 0.5840(5) 0.3848(2) 0.0578(9) Uani 1 1 d .
H14A H 0.8846 0.6782 0.3607 0.087 Uiso 1 1 calc GR
H14B H 0.9364 0.5023 0.3499 0.087 Uiso 1 1 calc GR
H14C H 1.0160 0.6126 0.4113 0.087 Uiso 1 1 calc GR
C15 C 0.8161(4) 0.6273(5) 0.4882(2) 0.0608(10) Uani 1 1 d .
H15A H 0.8994 0.6739 0.5136 0.091 Uiso 1 1 calc GR
H15B H 0.7732 0.5683 0.5212 0.091 Uiso 1 1 calc GR
H15C H 0.7567 0.7120 0.4662 0.091 Uiso 1 1 calc GR
C16 C 0.7897(3) 0.3756(3) 0.42415(15) 0.0344(6) Uani 1 1 d .
H16 H 0.8077 0.3183 0.3849 0.041 Uiso 1 1 calc R
H1 H 0.705(3) 0.088(4) 0.5103(16) 0.031(8) Uiso 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'
Br Br -0.2901 2.4595 '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_3
C8 N1 C7 122.43(19) .
C2 C1 C7 120.3(2) .
C6 C1 C2 118.9(2) .
C6 C1 C7 120.8(2) .
C1 C2 C3 120.4(2) .
C4 C3 C2 120.2(3) .
C5 C4 C3 119.6(2) .
C4 C5 C6 120.6(2) .
C1 C6 C5 120.3(3) .
N1 C7 C1 113.03(19) .
N1 C7 C7 107.4(2) 3_656
C1 C7 C7 111.3(2) 3_656
N1 C8 C9 123.4(2) .
N1 C8 C13 118.6(2) .
C9 C8 C13 117.8(2) .
C10 C9 C8 120.7(2) .
C11 C10 C9 119.9(2) .
C10 C11 Br1 120.03(19) .
C10 C11 C12 120.5(2) .
C12 C11 Br1 119.47(19) .
C13 C12 C11 119.6(2) .
C12 C13 C8 121.4(2) .
C15 N2 C14 117.3(3) .
C16 N2 C14 120.0(3) .
C16 N2 C15 122.5(3) .
O1 C16 N2 127.8(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C11 1.906(2) .
N1 C7 1.454(3) .
N1 C8 1.378(3) .
C1 C2 1.394(4) .
C1 C6 1.392(3) .
C1 C7 1.523(3) .
C2 C3 1.394(4) .
C3 C4 1.386(4) .
C4 C5 1.379(4) .
C5 C6 1.392(4) .
C7 C7 1.552(4) 3_656
C8 C9 1.399(3) .
C8 C13 1.402(3) .
C9 C10 1.394(3) .
C10 C11 1.379(4) .
C11 C12 1.385(4) .
C12 C13 1.382(3) .
O1 C16 1.216(3) .
N2 C14 1.474(4) .
N2 C15 1.416(4) .
N2 C16 1.314(4) .
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
N1 H1 O1 0.88(3) 2.06(3) 2.935(3) 170(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
_geom_torsion_site_symmetry_4
Br1 C11 C12 C13 -179.28(19) .
N1 C8 C9 C10 176.1(2) .
N1 C8 C13 C12 -176.9(2) .
C1 C2 C3 C4 0.7(4) .
C2 C1 C6 C5 0.1(3) .
C2 C1 C7 N1 50.2(3) .
C2 C1 C7 C7 -70.7(3) 3_656
C2 C3 C4 C5 0.1(4) .
C3 C4 C5 C6 -0.8(4) .
C4 C5 C6 C1 0.6(4) .
C6 C1 C2 C3 -0.8(4) .
C6 C1 C7 N1 -130.4(2) .
C6 C1 C7 C7 108.7(3) 3_656
C7 N1 C8 C9 18.6(4) .
C7 N1 C8 C13 -165.4(2) .
C7 C1 C2 C3 178.6(2) .
C7 C1 C6 C5 -179.2(2) .
C8 N1 C7 C1 67.5(3) .
C8 N1 C7 C7 -169.4(2) 3_656
C8 C9 C10 C11 1.0(4) .
C9 C8 C13 C12 -0.7(4) .
C9 C10 C11 Br1 178.7(2) .
C9 C10 C11 C12 -1.5(4) .
C10 C11 C12 C13 0.9(4) .
C11 C12 C13 C8 0.3(4) .
C13 C8 C9 C10 0.1(4) .
C14 N2 C16 O1 -179.5(3) .
C15 N2 C16 O1 -5.7(5) .
