#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/71/7117155.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_7117155
loop_
_publ_author_name
'Mingxia Ma'
'Yuanyuan Zhu'
'Quantao Sun'
'Xiaoyuan Li'
'Jinhuan Su'
'Long Zhao'
'Yanyan Zhao'
'Shuai Qiu'
'Wenjin Yan'
'Kairong Wang'
'Rui Wang'
_publ_section_title
;
 The asymmetric synthesis of CF3-containing
 spiro[pyrrolidin-3,2'-oxindole] through the organocatalytic 1,3-dipolar
 cycloaddition reaction
;
_journal_name_full               Chem.Commun.
_journal_page_first              8789
_journal_paper_doi               10.1039/C4cc10216A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C11 H8 Br F3 N2 O'
_chemical_formula_weight         321.10
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc144g0r
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-02-03 deposited with the CCDC.
2015-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.467(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8291(12)
_cell_length_b                   12.139(2)
_cell_length_c                   14.882(3)
_cell_measurement_temperature    296(2)
_cell_volume                     1209.1(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SMART'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       '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  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5971
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    3.427
_exptl_absorpt_correction_T_max  0.4471
_exptl_absorpt_correction_T_min  0.4263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yelllow
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0075(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2127
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0301
_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)+(0.0430P)²+0.3819P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0820
_reflns_number_gt                1710
_reflns_number_total             2127
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc10216a2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7117155
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.38502(5) -0.20095(2) 0.01715(2) 0.05924(17) Uani 1 1 d . . .
O1 O -0.1259(3) 0.26955(18) 0.22984(15) 0.0633(6) Uani 1 1 d . . .
N1 N -0.1372(3) 0.0815(2) 0.20754(16) 0.0476(6) Uani 1 1 d . . .
N2 N 0.1979(4) 0.25023(19) 0.11387(17) 0.0476(6) Uani 1 1 d . . .
C1 C 0.2139(4) -0.1171(2) 0.07743(19) 0.0443(6) Uani 1 1 d . . .
C2 C 0.2389(4) -0.0029(2) 0.08255(18) 0.0425(7) Uani 1 1 d . . .
H2 H 0.3355 0.0320 0.0566 0.051 Uiso 1 1 calc R . .
C3 C 0.1153(4) 0.0563(2) 0.12752(18) 0.0395(6) Uani 1 1 d . . .
C4 C -0.0330(4) 0.0029(2) 0.16562(18) 0.0424(6) Uani 1 1 d . . .
C5 C -0.0598(5) -0.1097(2) 0.1586(2) 0.0512(7) Uani 1 1 d . . .
H5 H -0.1588 -0.1449 0.1827 0.061 Uiso 1 1 calc R . .
C6 C 0.0681(5) -0.1685(2) 0.1139(2) 0.0521(8) Uani 1 1 d . . .
H6 H 0.0544 -0.2446 0.1085 0.063 Uiso 1 1 calc R . .
C7 C 0.0981(4) 0.1744(2) 0.14369(19) 0.0416(6) Uani 1 1 d . . .
C8 C -0.0672(4) 0.1854(2) 0.1989(2) 0.0466(7) Uani 1 1 d . . .
C9 C -0.3034(5) 0.0587(3) 0.2533(2) 0.0676(10) Uani 1 1 d . . .
H9A H -0.2597 0.0678 0.3183 0.101 Uiso 1 1 calc R . .
H9B H -0.3487 -0.0155 0.2404 0.101 Uiso 1 1 calc R . .
H9C H -0.4109 0.1089 0.2314 0.101 Uiso 1 1 calc R . .
C10 C 0.1565(5) 0.3650(2) 0.1324(2) 0.0548(8) Uani 1 1 d . . .
H10A H 0.1933 0.3794 0.1977 0.066 Uiso 1 1 calc R . .
H10B H 0.0149 0.3799 0.1127 0.066 Uiso 1 1 calc R . .
C11 C 0.2728(6) 0.4373(3) 0.0823(3) 0.0655(9) Uani 1 1 d . . .
F1 F 0.4684(3) 0.41770(17) 0.10307(17) 0.0869(7) Uani 1 1 d . . .
F2 F 0.2184(4) 0.4278(2) -0.00819(15) 0.0987(8) Uani 1 1 d . . .
F3 F 0.2479(4) 0.54358(16) 0.10300(19) 0.1028(8) Uani 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'
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'
F F 0.0171 0.0103 '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
C8 N1 C4 111.5(2) . .
C8 N1 C9 122.5(3) . .
C4 N1 C9 125.9(3) . .
C7 N2 C10 119.1(2) . .
C6 C1 C2 121.3(3) . .
C6 C1 Br1 120.2(2) . .
C2 C1 Br1 118.5(2) . .
C3 C2 C1 117.6(2) . .
C3 C2 H2 121.2 . .
C1 C2 H2 121.2 . .
C2 C3 C4 120.9(2) . .
C2 C3 C7 131.9(2) . .
C4 C3 C7 107.2(2) . .
C5 C4 N1 129.3(3) . .
C5 C4 C3 121.3(3) . .
N1 C4 C3 109.5(2) . .
C4 C5 C6 117.1(3) . .
C4 C5 H5 121.4 . .
C6 C5 H5 121.4 . .
C1 C6 C5 121.8(3) . .
C1 C6 H6 119.1 . .
C5 C6 H6 119.1 . .
N2 C7 C3 125.7(3) . .
N2 C7 C8 128.8(3) . .
C3 C7 C8 105.4(2) . .
O1 C8 N1 126.3(3) . .
O1 C8 C7 127.5(3) . .
N1 C8 C7 106.3(2) . .
N1 C9 H9A 109.5 . .
N1 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
N1 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
N2 C10 C11 109.1(3) . .
N2 C10 H10A 109.9 . .
C11 C10 H10A 109.9 . .
N2 C10 H10B 109.9 . .
C11 C10 H10B 109.9 . .
H10A C10 H10B 108.3 . .
F2 C11 F1 106.5(3) . .
F2 C11 F3 107.0(3) . .
F1 C11 F3 106.6(3) . .
F2 C11 C10 112.9(3) . .
F1 C11 C10 113.0(3) . .
F3 C11 C10 110.4(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.904(3) .
O1 C8 1.220(3) .
N1 C8 1.364(4) .
N1 C4 1.408(3) .
N1 C9 1.461(3) .
N2 C7 1.276(4) .
N2 C10 1.459(4) .
C1 C6 1.374(4) .
C1 C2 1.397(4) .
C2 C3 1.378(4) .
C2 H2 0.9300 .
C3 C4 1.412(4) .
C3 C7 1.463(4) .
C4 C5 1.381(4) .
C5 C6 1.395(4) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 C8 1.529(4) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 C11 1.480(4) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 F2 1.329(4) .
C11 F1 1.332(4) .
C11 F3 1.345(4) .
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 1.6(4) . . . .
Br1 C1 C2 C3 -179.2(2) . . . .
C1 C2 C3 C4 -1.0(4) . . . .
C1 C2 C3 C7 -178.6(3) . . . .
C8 N1 C4 C5 -179.3(3) . . . .
C9 N1 C4 C5 -0.7(5) . . . .
C8 N1 C4 C3 0.4(3) . . . .
C9 N1 C4 C3 179.1(3) . . . .
C2 C3 C4 C5 -0.4(4) . . . .
C7 C3 C4 C5 177.7(3) . . . .
C2 C3 C4 N1 179.8(2) . . . .
C7 C3 C4 N1 -2.0(3) . . . .
N1 C4 C5 C6 -179.2(3) . . . .
C3 C4 C5 C6 1.1(4) . . . .
C2 C1 C6 C5 -0.9(5) . . . .
Br1 C1 C6 C5 179.9(2) . . . .
C4 C5 C6 C1 -0.5(5) . . . .
C10 N2 C7 C3 177.1(3) . . . .
C10 N2 C7 C8 0.0(5) . . . .
C2 C3 C7 N2 2.8(5) . . . .
C4 C3 C7 N2 -175.0(3) . . . .
C2 C3 C7 C8 -179.5(3) . . . .
C4 C3 C7 C8 2.7(3) . . . .
C4 N1 C8 O1 -178.5(3) . . . .
C9 N1 C8 O1 2.8(5) . . . .
C4 N1 C8 C7 1.3(3) . . . .
C9 N1 C8 C7 -177.4(3) . . . .
N2 C7 C8 O1 -5.1(5) . . . .
C3 C7 C8 O1 177.3(3) . . . .
N2 C7 C8 N1 175.2(3) . . . .
C3 C7 C8 N1 -2.4(3) . . . .
C7 N2 C10 C11 -173.5(3) . . . .
N2 C10 C11 F2 64.4(4) . . . .
N2 C10 C11 F1 -56.6(4) . . . .
N2 C10 C11 F3 -175.9(3) . . . .
