#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/79/7117947.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_7117947
loop_
_publ_author_name
'Guodong Zhu'
'Baomin Wang'
'Xiaoze Bao'
'Huanrui Zhang'
'Qian Wei'
'Jingping Qu'
_publ_section_title
;
 Catalytic asymmetric construction of spiro[pyrrolidine-2,3'-oxindole]
 scaffolds through chiral phosphoric acid-catalyzed 1,3-dipolar
 cycloaddition involving 3-amino oxindoles
;
_journal_name_full               Chem.Commun.
_journal_page_first              15510
_journal_paper_doi               10.1039/C5cc05798A
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C30 H24 Br N3 O3'
_chemical_formula_weight         554.43
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-03-05 deposited with the CCDC.
2015-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8543(2)
_cell_length_b                   13.1630(2)
_cell_length_c                   17.7406(3)
_cell_measurement_temperature    296(2)
_cell_volume                     2534.69(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'pi 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  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0548
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13755
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    1.660
_exptl_absorpt_correction_T_max  0.6447
_exptl_absorpt_correction_T_min  0.5864
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.012(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4435
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0312
_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)+(0.0280P)²+0.0800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0766
_reflns_number_gt                3776
_reflns_number_total             4435
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc05798a2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P2(1)2(1)2(1) '
_cod_database_code               7117947
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.30462(3) 0.78359(2) 0.91165(2) 0.07022(13) Uani 1 1 d . . .
N3 N -0.12401(19) 1.16403(16) 0.87042(11) 0.0374(5) Uani 1 1 d . . .
O1 O 0.02022(17) 1.25614(13) 0.93669(10) 0.0461(5) Uani 1 1 d . . .
N1 N -0.1870(2) 1.23748(15) 1.04921(11) 0.0402(5) Uani 1 1 d . . .
H1A H -0.2552 1.2685 1.0404 0.048 Uiso 1 1 calc R . .
C17 C 0.1959(3) 0.88036(19) 0.95561(15) 0.0435(6) Uani 1 1 d . . .
C3 C -0.0502(2) 1.09608(18) 1.05714(13) 0.0328(5) Uani 1 1 d . . .
H3A H -0.1023 1.0569 1.0916 0.039 Uiso 1 1 calc R . .
N2 N 0.0569(2) 1.15075(19) 1.17600(13) 0.0466(6) Uani 1 1 d . . .
C6 C -0.2217(2) 1.09771(18) 0.88801(13) 0.0363(6) Uani 1 1 d . . .
C27 C -0.2972(3) 1.0452(2) 0.83965(15) 0.0467(6) Uani 1 1 d . . .
H27A H -0.2892 1.0519 0.7877 0.056 Uiso 1 1 calc R . .
C7 C -0.2344(2) 1.08991(19) 0.96529(14) 0.0354(6) Uani 1 1 d . . .
C14 C 0.0385(2) 1.02204(17) 1.02089(14) 0.0337(6) Uani 1 1 d . . .
C5 C -0.0686(2) 1.19913(18) 0.93427(13) 0.0356(6) Uani 1 1 d . . .
C1 C -0.1045(2) 1.26100(18) 1.11297(14) 0.0382(6) Uani 1 1 d . . .
H1B H -0.0718 1.3297 1.1058 0.046 Uiso 1 1 calc R . .
C28 C -0.3865(3) 0.9816(2) 0.87092(19) 0.0544(8) Uani 1 1 d . . .
H28A H -0.4389 0.9453 0.8394 0.065 Uiso 1 1 calc R . .
C22 C 0.0756(3) 1.0469(2) 0.79619(16) 0.0509(7) Uani 1 1 d . . .
H22A H 0.0879 1.0595 0.8472 0.061 Uiso 1 1 calc R . .
O3 O 0.1296(2) 1.2087(2) 1.20554(13) 0.0727(6) Uani 1 1 d . . .
C2 C 0.0035(2) 1.18358(18) 1.10205(14) 0.0364(5) Uani 1 1 d . . .
H2A H 0.0684 1.2160 1.0721 0.044 Uiso 1 1 calc R . .
C21 C -0.0127(2) 1.10134(19) 0.75714(14) 0.0375(6) Uani 1 1 d . . .
C10 C -0.3107(3) 1.1850(2) 1.27891(18) 0.0616(8) Uani 1 1 d . . .
H10A H -0.3731 1.1389 1.2898 0.074 Uiso 1 1 calc R . .
C4 C -0.1381(2) 1.15480(17) 1.00279(14) 0.0340(5) Uani 1 1 d . . .
C8 C -0.1661(2) 1.25635(18) 1.18994(14) 0.0392(6) Uani 1 1 d . . .
C30 C -0.3218(2) 1.0268(2) 0.99596(16) 0.0457(7) Uani 1 1 d . . .
H30A H -0.3299 1.0210 1.0480 0.055 Uiso 1 1 calc R . .
C20 C -0.0823(3) 1.1873(2) 0.79438(14) 0.0440(7) Uani 1 1 d . . .
H20A H -0.0295 1.2467 0.7962 0.053 Uiso 1 1 calc R . .
H20B H -0.1533 1.2041 0.7636 0.053 Uiso 1 1 calc R . .
C15 C 0.1606(2) 1.0456(2) 1.00576(15) 0.0402(6) Uani 1 1 d . . .
H15A H 0.1905 1.1098 1.0178 0.048 Uiso 1 1 calc R . .
C19 C -0.0023(3) 0.92541(19) 1.00196(17) 0.0489(7) Uani 1 1 d . . .
H19A H -0.0839 0.9082 1.0116 0.059 Uiso 1 1 calc R . .
C24 C 0.1275(3) 0.9524(2) 0.68578(18) 0.0531(8) Uani 1 1 d . . .
H24A H 0.1739 0.9024 0.6620 0.064 Uiso 1 1 calc R . .
C23 C 0.1462(3) 0.9737(2) 0.76012(18) 0.0583(8) Uani 1 1 d . . .
H23A H 0.2067 0.9389 0.7868 0.070 Uiso 1 1 calc R . .
C29 C -0.3979(3) 0.9717(2) 0.94788(18) 0.0544(8) Uani 1 1 d . . .
H29A H -0.4568 0.9279 0.9678 0.065 Uiso 1 1 calc R . .
C26 C -0.0302(3) 1.0788(2) 0.68157(16) 0.0520(7) Uani 1 1 d . . .
H26A H -0.0899 1.1135 0.6542 0.062 Uiso 1 1 calc R . .
C9 C -0.2585(3) 1.1884(2) 1.20733(16) 0.0471(7) Uani 1 1 d . . .
H9A H -0.2865 1.1439 1.1704 0.057 Uiso 1 1 calc R . .
C16 C 0.2388(3) 0.9750(2) 0.97308(16) 0.0471(7) Uani 1 1 d . . .
H16A H 0.3204 0.9920 0.9631 0.056 Uiso 1 1 calc R . .
O2 O 0.0233(2) 1.07074(18) 1.20315(12) 0.0652(6) Uani 1 1 d . . .
C12 C -0.1785(4) 1.3204(3) 1.31677(19) 0.0729(10) Uani 1 1 d . . .
H12A H -0.1513 1.3656 1.3535 0.088 Uiso 1 1 calc R . .
C13 C -0.1274(3) 1.3232(2) 1.24468(17) 0.0570(8) Uani 1 1 d . . .
H13A H -0.0667 1.3707 1.2335 0.068 Uiso 1 1 calc R . .
C18 C 0.0741(3) 0.8540(2) 0.96936(18) 0.0552(8) Uani 1 1 d . . .
H18A H 0.0447 0.7898 0.9569 0.066 Uiso 1 1 calc R . .
C11 C -0.2683(4) 1.2514(3) 1.33361(19) 0.0726(11) Uani 1 1 d . . .
H11A H -0.3011 1.2490 1.3820 0.087 Uiso 1 1 calc R . .
C25 C 0.0403(3) 1.0051(3) 0.64652(18) 0.0599(9) Uani 1 1 d . . .
H25B H 0.0282 0.9913 0.5956 0.072 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C5 N3 C6 110.99(19) . .
C5 N3 C20 124.2(2) . .
C6 N3 C20 124.7(2) . .
C4 N1 C1 111.55(18) . .
C16 C17 C18 120.8(3) . .
C16 C17 Br1 119.5(2) . .
C18 C17 Br1 119.7(2) . .
C14 C3 C2 117.9(2) . .
C14 C3 C4 116.4(2) . .
C2 C3 C4 100.56(18) . .
O2 N2 O3 124.6(3) . .
O2 N2 C2 118.8(2) . .
O3 N2 C2 116.6(2) . .
C27 C6 C7 121.5(2) . .
C27 C6 N3 128.5(2) . .
C7 C6 N3 109.9(2) . .
C6 C27 C28 117.9(3) . .
C30 C7 C6 120.5(2) . .
C30 C7 C4 130.4(2) . .
C6 C7 C4 109.1(2) . .
C15 C14 C19 117.5(2) . .
C15 C14 C3 123.1(2) . .
C19 C14 C3 119.4(2) . .
O1 C5 N3 125.8(2) . .
O1 C5 C4 126.1(2) . .
N3 C5 C4 108.1(2) . .
N1 C1 C8 114.4(2) . .
N1 C1 C2 102.88(18) . .
C8 C1 C2 114.45(19) . .
C29 C28 C27 120.9(3) . .
C21 C22 C23 120.8(3) . .
N2 C2 C3 112.9(2) . .
N2 C2 C1 111.66(19) . .
C3 C2 C1 105.75(19) . .
C22 C21 C26 118.0(3) . .
C22 C21 C20 121.0(2) . .
C26 C21 C20 120.9(2) . .
C11 C10 C9 118.9(3) . .
N1 C4 C7 114.74(19) . .
N1 C4 C5 109.80(19) . .
C7 C4 C5 101.9(2) . .
N1 C4 C3 104.01(19) . .
C7 C4 C3 114.61(19) . .
C5 C4 C3 112.00(18) . .
C13 C8 C9 118.6(3) . .
C13 C8 C1 118.3(3) . .
C9 C8 C1 123.1(2) . .
C7 C30 C29 118.9(3) . .
N3 C20 C21 113.8(2) . .
C16 C15 C14 121.1(2) . .
C18 C19 C14 122.3(3) . .
C23 C24 C25 119.5(3) . .
C24 C23 C22 120.4(3) . .
C28 C29 C30 120.3(3) . .
C25 C26 C21 120.6(3) . .
C8 C9 C10 121.4(3) . .
C17 C16 C15 119.9(3) . .
C11 C12 C13 120.2(3) . .
C8 C13 C12 120.6(3) . .
C19 C18 C17 118.4(3) . .
C12 C11 C10 120.2(3) . .
C24 C25 C26 120.7(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C17 1.903(3) .
N3 C5 1.363(3) .
N3 C6 1.408(3) .
N3 C20 1.455(3) .
O1 C5 1.222(3) .
N1 C4 1.464(3) .
N1 C1 1.475(3) .
C17 C16 1.365(4) .
C17 C18 1.389(4) .
C3 C14 1.513(3) .
C3 C2 1.517(3) .
C3 C4 1.561(3) .
N2 O2 1.214(3) .
N2 O3 1.216(3) .
N2 C2 1.498(3) .
C6 C27 1.373(4) .
C6 C7 1.382(3) .
C27 C28 1.396(4) .
C7 C30 1.374(3) .
C7 C4 1.505(3) .
C14 C15 1.388(3) .
C14 C19 1.388(4) .
C5 C4 1.545(3) .
C1 C8 1.521(4) .
C1 C2 1.566(3) .
C28 C29 1.377(4) .
C22 C21 1.383(4) .
C22 C23 1.388(4) .
C21 C26 1.386(4) .
C21 C20 1.512(4) .
C10 C11 1.385(5) .
C10 C9 1.391(4) .
C8 C13 1.376(4) .
C8 C9 1.378(4) .
C30 C29 1.392(4) .
C15 C16 1.386(4) .
C19 C18 1.380(4) .
C24 C23 1.363(4) .
C24 C25 1.364(4) .
C26 C25 1.384(4) .
C12 C11 1.365(5) .
C12 C13 1.395(5) .
