#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:48:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180277 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/63/7116337.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_7116337
loop_
_publ_author_name
'Pei-Qiang Huang'
'Qi-Wei Lang'
'Ai-E Wang'
'Jian-Feng Zheng'
_publ_section_title
;
 Direct reductive coupling of secondary amides: chemoselective formation
 of vicinal diamines and vicinal amino alcohols
;
_journal_name_full               Chem.Commun.
_journal_page_first              1096
_journal_paper_doi               10.1039/C4cc08330J
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C26 H34 Br2 N2'
_chemical_formula_weight         534.37
_chemical_name_systematic
; 
 ? 
;
_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                93.862(10)
_cell_angle_beta                 91.455(9)
_cell_angle_gamma                96.575(9)
_cell_formula_units_Z            1
_cell_length_a                   5.9858(5)
_cell_length_b                   10.0355(12)
_cell_length_c                   10.1711(12)
_cell_measurement_reflns_used    1266
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.3720
_cell_measurement_theta_min      3.4170
_cell_volume                     605.25(11)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'multiwire proportional'
_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  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4235
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    3.364
_exptl_absorpt_correction_T_max  0.7297
_exptl_absorpt_correction_T_min  0.4319
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             274
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.787
_refine_diff_density_min         -0.697
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0392P)²+0.2410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0966
_reflns_number_gt                2121
_reflns_number_total             2385
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc08330j2.cif
_cod_data_source_block           m1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7116337
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
Br1 Br 1.03383(6) 1.25062(4) 0.00313(3) 0.04375(16) Uani 1 1 d .
N1 N 0.6217(4) 0.8387(2) 0.4661(2) 0.0205(5) Uani 1 1 d .
H1A H 0.6761 0.8292 0.5457 0.025 Uiso 1 1 calc R
C1 C 0.5070(4) 0.9555(3) 0.4355(3) 0.0196(6) Uani 1 1 d .
H1B H 0.3512 0.9233 0.4006 0.023 Uiso 1 1 calc R
C8 C 0.8700(5) 1.1655(3) 0.1384(3) 0.0249(6) Uani 1 1 d .
C2 C 0.6399(4) 0.7389(3) 0.3556(3) 0.0214(6) Uani 1 1 d .
H2A H 0.7280 0.7847 0.2858 0.026 Uiso 1 1 calc R
C9 C 0.5315(5) 1.0477(3) 0.2104(3) 0.0222(6) Uani 1 1 d .
H9A H 0.3787 1.0119 0.1937 0.027 Uiso 1 1 calc R
C10 C 0.6474(5) 1.1145(3) 0.1135(3) 0.0250(6) Uani 1 1 d .
H10A H 0.5751 1.1250 0.0313 0.030 Uiso 1 1 calc R
C11 C 0.8580(5) 1.0873(3) 0.3546(3) 0.0231(6) Uani 1 1 d .
H11A H 0.9304 1.0791 0.4374 0.028 Uiso 1 1 calc R
C3 C 0.4454(5) 0.5691(3) 0.1815(3) 0.0340(7) Uani 1 1 d .
H3A H 0.2963 0.5275 0.1460 0.041 Uiso 1 1 calc R
H3B H 0.5261 0.6130 0.1093 0.041 Uiso 1 1 calc R
C12 C 0.6340(4) 1.0321(2) 0.3315(3) 0.0181(5) Uani 1 1 d .
C13 C 0.9759(5) 1.1542(3) 0.2577(3) 0.0246(6) Uani 1 1 d .
H13A H 1.1280 1.1917 0.2740 0.029 Uiso 1 1 calc R
C4 C 0.7725(5) 0.6297(3) 0.4043(3) 0.0280(7) Uani 1 1 d .
H4A H 0.6921 0.5867 0.4771 0.034 Uiso 1 1 calc R
H4B H 0.9219 0.6713 0.4395 0.034 Uiso 1 1 calc R
C5 C 0.4138(5) 0.6752(3) 0.2932(3) 0.0294(7) Uani 1 1 d .
H5A H 0.3323 0.7462 0.2580 0.035 Uiso 1 1 calc R
H5B H 0.3212 0.6326 0.3617 0.035 Uiso 1 1 calc R
C6 C 0.8044(6) 0.5221(3) 0.2945(3) 0.0355(7) Uani 1 1 d .
H6A H 0.8814 0.4502 0.3316 0.043 Uiso 1 1 calc R
H6B H 0.9009 0.5628 0.2267 0.043 Uiso 1 1 calc R
C7 C 0.5778(6) 0.4611(3) 0.2304(4) 0.0393(8) Uani 1 1 d .
H7A H 0.6042 0.3972 0.1554 0.047 Uiso 1 1 calc R
H7B H 0.4890 0.4104 0.2954 0.047 Uiso 1 1 calc R
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 N1 C1 115.9(2) . .
C2 N1 H1A 122.1 . .
C1 N1 H1A 122.1 . .
N1 C1 C12 109.7(2) . .
N1 C1 C1 108.3(3) . 2_676
C12 C1 C1 111.7(3) . 2_676
N1 C1 H1B 109.0 . .
C12 C1 H1B 109.0 . .
C1 C1 H1B 109.0 2_676 .
C13 C8 C10 121.4(3) . .
C13 C8 Br1 119.4(2) . .
C10 C8 Br1 119.2(2) . .
N1 C2 C4 108.3(2) . .
N1 C2 C5 114.5(2) . .
C4 C2 C5 109.9(2) . .
N1 C2 H2A 108.0 . .
C4 C2 H2A 108.0 . .
C5 C2 H2A 108.0 . .
C10 C9 C12 121.3(2) . .
C10 C9 H9A 119.3 . .
C12 C9 H9A 119.3 . .
C8 C10 C9 119.0(3) . .
C8 C10 H10A 120.5 . .
C9 C10 H10A 120.5 . .
C13 C11 C12 120.7(2) . .
C13 C11 H11A 119.6 . .
C12 C11 H11A 119.6 . .
C7 C3 C5 111.0(3) . .
C7 C3 H3A 109.4 . .
C5 C3 H3A 109.4 . .
C7 C3 H3B 109.4 . .
C5 C3 H3B 109.4 . .
H3A C3 H3B 108.0 . .
C9 C12 C11 118.3(2) . .
C9 C12 C1 120.8(2) . .
C11 C12 C1 120.9(2) . .
C8 C13 C11 119.2(2) . .
C8 C13 H13A 120.4 . .
C11 C13 H13A 120.4 . .
C2 C4 C6 112.1(2) . .
C2 C4 H4A 109.2 . .
C6 C4 H4A 109.2 . .
C2 C4 H4B 109.2 . .
C6 C4 H4B 109.2 . .
H4A C4 H4B 107.9 . .
C2 C5 C3 111.6(2) . .
C2 C5 H5A 109.3 . .
C3 C5 H5A 109.3 . .
C2 C5 H5B 109.3 . .
C3 C5 H5B 109.3 . .
H5A C5 H5B 108.0 . .
C4 C6 C7 111.2(3) . .
C4 C6 H6A 109.4 . .
C7 C6 H6A 109.4 . .
C4 C6 H6B 109.4 . .
C7 C6 H6B 109.4 . .
H6A C6 H6B 108.0 . .
C3 C7 C6 111.3(2) . .
C3 C7 H7A 109.4 . .
C6 C7 H7A 109.4 . .
C3 C7 H7B 109.4 . .
C6 C7 H7B 109.4 . .
H7A C7 H7B 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C8 1.902(3) .
N1 C2 1.468(3) .
N1 C1 1.471(3) .
N1 H1A 0.8800 .
C1 C12 1.518(4) .
C1 C1 1.546(5) 2_676
C1 H1B 1.0000 .
C8 C13 1.373(4) .
C8 C10 1.382(4) .
C2 C4 1.526(4) .
C2 C5 1.532(4) .
C2 H2A 1.0000 .
C9 C10 1.385(4) .
C9 C12 1.388(4) .
C9 H9A 0.9500 .
C10 H10A 0.9500 .
C11 C13 1.391(4) .
C11 C12 1.399(4) .
C11 H11A 0.9500 .
C3 C7 1.517(5) .
C3 C5 1.534(4) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C13 H13A 0.9500 .
C4 C6 1.531(4) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C7 1.533(5) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
