#------------------------------------------------------------------------------
#$Date: 2017-02-04 16:15:02 +0200 (Sat, 04 Feb 2017) $
#$Revision: 191750 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/54/7155436.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_7155436
loop_
_publ_author_name
'Chen, Pengquan'
'Zhu, Chuanle'
'Zhu, Rui'
'Lin, Zhiming'
'Wu, Wanqing'
'Jiang, Huanfeng'
_publ_section_title
;
 Synthesis of 3-azabicyclo[3.1.0]hexane derivatives via
 palladium-catalyzed cyclopropanation of maleimides with
 N-tosylhydrazones: practical and facile access to CP-866,087.
;
_journal_issue                   5
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1228
_journal_page_last               1235
_journal_paper_doi               10.1039/c6ob02137a
_journal_volume                  15
_journal_year                    2017
_chemical_formula_sum            'C16 H18 Br N O2'
_chemical_formula_weight         336.22
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_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
_audit_update_record
;
2016-07-01 deposited with the CCDC.
2017-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.19(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9645(14)
_cell_length_b                   14.893(3)
_cell_length_c                   14.570(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1482.5(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8027
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    2.774
_exptl_absorpt_correction_T_max  0.7689
_exptl_absorpt_correction_T_min  0.7689
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       0.0032(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2607
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0396
_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)+(0.0357P)²+3.6372P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.1299
_reflns_number_gt                1767
_reflns_number_total             2607
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob02137a2.cif
_cod_data_source_block           chen
_cod_depositor_comments
'Adding full bibliography for 7155436--7155437.cif.'
_cod_database_code               7155436
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
Br1 Br 0.37695(8) 0.40550(4) 0.85848(5) 0.0606(3) Uani 1 1 d .
N1 N 1.2278(5) 0.7631(3) 1.0361(3) 0.0395(9) Uani 1 1 d .
C9 C 1.0189(7) 0.6393(3) 1.0035(3) 0.0401(11) Uani 1 1 d .
H9A H 0.9879 0.5834 1.0331 0.048 Uiso 1 1 calc R
C8 C 1.1614(6) 0.6375(3) 0.9396(3) 0.0402(11) Uani 1 1 d .
H8A H 1.2225 0.5805 0.9279 0.048 Uiso 1 1 calc R
C1 C 0.5983(7) 0.4601(3) 0.8247(4) 0.0442(12) Uani 1 1 d .
C10 C 1.0669(7) 0.7208(3) 1.0614(3) 0.0411(12) Uani 1 1 d .
C7 C 0.9467(6) 0.6525(3) 0.8993(3) 0.0385(11) Uani 1 1 d .
C5 C 0.8492(7) 0.5716(3) 0.8490(3) 0.0373(11) Uani 1 1 d .
C11 C 1.2855(7) 0.7184(4) 0.9625(4) 0.0449(12) Uani 1 1 d .
C6 C 0.6841(6) 0.5339(3) 0.8728(3) 0.0405(12) Uani 1 1 d .
H6A H 0.6312 0.5583 0.9211 0.049 Uiso 1 1 calc R
C12 C 1.3144(8) 0.8472(3) 1.0834(4) 0.0478(13) Uani 1 1 d .
C4 C 0.9206(8) 0.5353(4) 0.7754(4) 0.0516(13) Uani 1 1 d .
H4A H 1.0293 0.5611 0.7575 0.062 Uiso 1 1 calc R
C2 C 0.6716(8) 0.4229(4) 0.7525(4) 0.0515(14) Uani 1 1 d .
H2A H 0.6128 0.3727 0.7211 0.062 Uiso 1 1 calc R
C3 C 0.8336(9) 0.4613(4) 0.7276(4) 0.0605(16) Uani 1 1 d .
H3A H 0.8846 0.4373 0.6785 0.073 Uiso 1 1 calc R
C16 C 0.8696(7) 0.7410(3) 0.8580(4) 0.0478(13) Uani 1 1 d .
H16A H 0.7305 0.7369 0.8369 0.072 Uiso 1 1 calc R
H16B H 0.9305 0.7554 0.8062 0.072 Uiso 1 1 calc R
H16C H 0.8986 0.7870 0.9048 0.072 Uiso 1 1 calc R
O1 O 1.4125(6) 0.7407(3) 0.9216(3) 0.0709(13) Uani 1 1 d .
O2 O 0.9806(6) 0.7463(3) 1.1204(3) 0.0596(10) Uani 1 1 d .
C14 C 1.1629(9) 0.9211(4) 1.0626(4) 0.0673(18) Uani 1 1 d .
H14A H 1.1303 0.9311 0.9963 0.101 Uiso 1 1 calc R
H14B H 1.2149 0.9753 1.0933 0.101 Uiso 1 1 calc R
H14C H 1.0474 0.9037 1.0849 0.101 Uiso 1 1 calc R
C13 C 1.3684(9) 0.8298(4) 1.1881(4) 0.0628(17) Uani 1 1 d .
H13A H 1.4641 0.7827 1.1999 0.094 Uiso 1 1 calc R
H13B H 1.2536 0.8121 1.2109 0.094 Uiso 1 1 calc R
H13C H 1.4216 0.8835 1.2195 0.094 Uiso 1 1 calc R
C15 C 1.4991(10) 0.8750(5) 1.0497(5) 0.080(2) Uani 1 1 d .
H15A H 1.4685 0.8857 0.9835 0.121 Uiso 1 1 calc R
H15B H 1.5946 0.8279 1.0630 0.121 Uiso 1 1 calc R
H15C H 1.5507 0.9288 1.0814 0.121 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'
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
C11 N1 C10 110.8(4)
C11 N1 C12 127.3(4)
C10 N1 C12 121.9(4)
C10 C9 C8 105.5(4)
C10 C9 C7 117.3(4)
C8 C9 C7 60.5(3)
C11 C8 C9 106.0(4)
C11 C8 C7 117.2(4)
C9 C8 C7 60.8(3)
C2 C1 C6 121.6(5)
C2 C1 Br1 118.0(4)
C6 C1 Br1 120.4(4)
O2 C10 N1 125.7(5)
O2 C10 C9 125.4(5)
N1 C10 C9 108.9(4)
C5 C7 C16 114.5(4)
C5 C7 C8 113.0(4)
C16 C7 C8 122.2(4)
C5 C7 C9 114.5(4)
C16 C7 C9 122.5(4)
C8 C7 C9 58.8(3)
C4 C5 C6 118.6(5)
C4 C5 C7 119.8(4)
C6 C5 C7 121.5(4)
O1 C11 N1 126.9(5)
O1 C11 C8 124.3(5)
N1 C11 C8 108.7(4)
C1 C6 C5 119.8(5)
N1 C12 C14 108.2(4)
N1 C12 C15 111.6(5)
C14 C12 C15 109.8(5)
N1 C12 C13 108.5(4)
C14 C12 C13 110.6(5)
C15 C12 C13 108.1(5)
C3 C4 C5 121.1(5)
C1 C2 C3 118.8(5)
C2 C3 C4 120.1(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.891(5)
N1 C11 1.386(6)
N1 C10 1.397(6)
N1 C12 1.498(6)
C9 C10 1.479(7)
C9 C8 1.487(7)
C9 C7 1.517(7)
C8 C11 1.482(7)
C8 C7 1.513(6)
C1 C2 1.371(7)
C1 C6 1.376(7)
C10 O2 1.202(6)
C7 C5 1.502(6)
C7 C16 1.503(7)
C5 C4 1.377(7)
C5 C6 1.383(6)
C11 O1 1.206(6)
C12 C14 1.513(7)
C12 C15 1.520(8)
C12 C13 1.521(7)
C4 C3 1.380(7)
C2 C3 1.375(8)
