#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:20:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178466 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/87/4028732.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_4028732
loop_
_publ_author_name
'Yu Peng'
'Long Luo'
'Chang-Song Yan'
'Jian-Jian Zhang'
'Ya-Wen Wang'
_publ_section_title
;
 Ni-Catalyzed Reductive Homocoupling of Unactivated Alkyl Bromides at Room
 Temperature and Its Synthetic Application
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10960
_journal_page_last               10967
_journal_paper_doi               10.1021/jo401936v
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C10 H18 N O2'
_chemical_formula_sum            'C10 H18 N O2'
_chemical_formula_weight         184.25
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 97.41(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.259(4)
_cell_length_b                   6.367(2)
_cell_length_c                   18.158(12)
_cell_measurement_reflns_used    1346
_cell_measurement_temperature    282(4)
_cell_measurement_theta_max      27.7210
_cell_measurement_theta_min      3.9080
_cell_volume                     1061.5(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      282(4)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0523
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4274
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.37
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         2154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0586
_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)+(0.0673P)²+0.2852P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.1677
_reflns_number_gt                1590
_reflns_number_total             2154
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401936v_si_003.cif
_cod_data_source_block           exp_697
_cod_database_code               4028732
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.29848(16) 0.5439(2) 0.28830(7) 0.0523(4) Uani 1 1 d .
O2 O 0.25909(18) 0.1934(2) 0.27964(8) 0.0624(5) Uani 1 1 d .
N3 N 0.15106(19) 0.4179(3) 0.19238(9) 0.0476(4) Uani 1 1 d .
C1 C 0.1087(3) 0.6302(3) 0.16891(11) 0.0504(5) Uani 1 1 d .
H1A H 0.1783 0.7298 0.1933 0.061 Uiso 1 1 calc R
H1B H 0.0138 0.6622 0.1833 0.061 Uiso 1 1 calc R
C2 C 0.1029(2) 0.6516(3) 0.08506(10) 0.0466(5) Uani 1 1 d .
H2A H 0.0679 0.7908 0.0703 0.056 Uiso 1 1 calc R
H2B H 0.2006 0.6372 0.0718 0.056 Uiso 1 1 calc R
C3 C 0.00466(19) 0.4889(3) 0.04265(9) 0.0372(4) Uani 1 1 d .
H3 H -0.0937 0.5089 0.0559 0.045 Uiso 1 1 calc R
C4 C 0.0567(2) 0.2737(3) 0.07051(11) 0.0488(5) Uani 1 1 d .
H4A H 0.1532 0.2486 0.0570 0.059 Uiso 1 1 calc R
H4B H -0.0081 0.1675 0.0464 0.059 Uiso 1 1 calc R
C5 C 0.0619(3) 0.2526(3) 0.15473(11) 0.0575(6) Uani 1 1 d .
H5A H -0.0361 0.2611 0.1681 0.069 Uiso 1 1 calc R
H5B H 0.1020 0.1167 0.1705 0.069 Uiso 1 1 calc R
C6 C 0.2383(2) 0.3707(3) 0.25588(11) 0.0440(5) Uani 1 1 d .
C7 C 0.3968(2) 0.5315(3) 0.35869(11) 0.0493(5) Uani 1 1 d .
C8 C 0.3180(3) 0.4359(5) 0.41894(13) 0.0741(8) Uani 1 1 d .
H8A H 0.2291 0.5114 0.4218 0.111 Uiso 1 1 calc R
H8B H 0.3790 0.4445 0.4658 0.111 Uiso 1 1 calc R
H8C H 0.2960 0.2914 0.4073 0.111 Uiso 1 1 calc R
C9 C 0.4317(3) 0.7600(4) 0.37443(15) 0.0816(9) Uani 1 1 d .
H9A H 0.4771 0.8183 0.3344 0.122 Uiso 1 1 calc R
H9B H 0.4968 0.7717 0.4199 0.122 Uiso 1 1 calc R
H9C H 0.3435 0.8352 0.3790 0.122 Uiso 1 1 calc R
C10 C 0.5317(3) 0.4114(5) 0.34710(14) 0.0708(7) Uani 1 1 d .
H10A H 0.5068 0.2674 0.3361 0.106 Uiso 1 1 calc R
H10B H 0.6005 0.4183 0.3914 0.106 Uiso 1 1 calc R
H10C H 0.5740 0.4717 0.3064 0.106 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'
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
C6 O1 C7 120.90(15) . .
C6 N3 C5 118.68(16) . .
C6 N3 C1 124.36(17) . .
C5 N3 C1 114.82(17) . .
N3 C1 C2 110.43(16) . .
N3 C1 H1A 109.6 . .
C2 C1 H1A 109.6 . .
N3 C1 H1B 109.6 . .
C2 C1 H1B 109.6 . .
H1A C1 H1B 108.1 . .
C3 C2 C1 112.80(16) . .
C3 C2 H2A 109.0 . .
C1 C2 H2A 109.0 . .
C3 C2 H2B 109.0 . .
C1 C2 H2B 109.0 . .
H2A C2 H2B 107.8 . .
C4 C3 C2 107.62(15) . .
C4 C3 C3 113.00(18) . 3_565
C2 C3 C3 113.42(18) . 3_565
C4 C3 H3 107.5 . .
C2 C3 H3 107.5 . .
C3 C3 H3 107.5 3_565 .
C3 C4 C5 112.36(17) . .
C3 C4 H4A 109.1 . .
C5 C4 H4A 109.1 . .
C3 C4 H4B 109.1 . .
C5 C4 H4B 109.1 . .
H4A C4 H4B 107.9 . .
N3 C5 C4 110.44(17) . .
N3 C5 H5A 109.6 . .
C4 C5 H5A 109.6 . .
N3 C5 H5B 109.6 . .
C4 C5 H5B 109.6 . .
H5A C5 H5B 108.1 . .
O2 C6 O1 124.88(18) . .
O2 C6 N3 123.98(18) . .
O1 C6 N3 111.14(16) . .
O1 C7 C10 109.74(18) . .
O1 C7 C9 101.87(16) . .
C10 C7 C9 110.8(2) . .
O1 C7 C8 110.25(18) . .
C10 C7 C8 112.5(2) . .
C9 C7 C8 111.2(2) . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C7 C9 H9A 109.5 . .
C7 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C7 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C7 C10 H10A 109.5 . .
C7 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C7 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C6 1.338(2) .
O1 C7 1.473(2) .
O2 C6 1.215(2) .
N3 C6 1.353(3) .
N3 C5 1.453(3) .
N3 C1 1.456(2) .
C1 C2 1.522(3) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 C3 1.521(3) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.517(3) .
C3 C3 1.546(4) 3_565
C3 H3 0.9800 .
C4 C5 1.530(3) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C7 C10 1.502(3) .
C7 C9 1.510(3) .
C7 C8 1.518(3) .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
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 N3 C1 C2 142.7(2) . .
C5 N3 C1 C2 -54.3(2) . .
N3 C1 C2 C3 54.8(2) . .
C1 C2 C3 C4 -55.3(2) . .
C1 C2 C3 C3 178.93(19) . 3_565
C2 C3 C4 C5 55.3(2) . .
C3 C3 C4 C5 -178.65(19) 3_565 .
C6 N3 C5 C4 -141.4(2) . .
C1 N3 C5 C4 54.5(3) . .
C3 C4 C5 N3 -55.3(3) . .
C7 O1 C6 O2 -0.9(3) . .
C7 O1 C6 N3 179.46(17) . .
C5 N3 C6 O2 8.3(3) . .
C1 N3 C6 O2 170.7(2) . .
C5 N3 C6 O1 -172.15(19) . .
C1 N3 C6 O1 -9.7(3) . .
C6 O1 C7 C10 64.5(2) . .
C6 O1 C7 C9 -178.1(2) . .
C6 O1 C7 C8 -60.0(2) . .
