Enantioselective synthesis of 3,3'-dihydropyrryl-spirooxindoles via an organocatalytic three-component reaction.
Wei, Wen-Tao; Chen, Chun-Xia; Lu, Rui-Jiong; Wang, Jin-Jia; Zhang, Xue-Jing; Yan, Ming; Organic & biomolecular chemistry 10 (2012) 5245–5252; doi:10.1039/c2ob25629k

data_7152426
_publ_section_title
;
 Enantioselective synthesis of 3,3'-dihydropyrryl-spirooxindoles via an
 organocatalytic three-component reaction.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5245
_journal_page_last               5252
_journal_paper_doi               10.1039/c2ob25629k
_journal_volume                  10
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H15 Br N4 O3'
_chemical_formula_sum            'C22 H15 Br N4 O3'
_chemical_formula_weight         463.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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_date             2011-12-08
_audit_creation_method
;
Olex2 1.1
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.26806(16)
_cell_length_b                   13.0043(2)
_cell_length_c                   16.2697(2)
_cell_measurement_reflns_used    6808
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      71.5624
_cell_measurement_theta_min      2.7137
_cell_volume                     1960.90(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 8.2417
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
1 omega -126.00 -80.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -42.2034 -99.0000 -180.0000 46

2 omega 75.00 118.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 42.2034 125.0000 -150.0000 43

3 omega 17.00 85.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 42.2034 57.0000 -120.0000 68

4 omega 34.00 59.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -30.0000 90.0000 25

5 omega 77.00 107.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -94.0000 -120.0000 30

6 omega 79.00 129.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -61.0000 60.0000 50

7 omega 68.00 177.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 15.0000 30.0000 109

8 omega 23.00 69.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -30.0000 -150.0000 46

9 omega 40.00 69.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -125.0000 -120.0000 29

10 omega 86.00 111.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -125.0000 -120.0000 25

11 omega 120.00 156.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 125.0000 0.0000 36

12 omega 64.00 102.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -77.0000 -90.0000 38

13 omega 43.00 69.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -109.0000 105.0000 26

14 omega 74.00 104.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -94.0000 150.0000 30

15 omega 25.00 67.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -30.0000 60.0000 42

16 omega 27.00 55.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -45.0000 -150.0000 28
;
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1453961000
_diffrn_orient_matrix_UB_12      0.0573554000
_diffrn_orient_matrix_UB_13      -0.0010341000
_diffrn_orient_matrix_UB_21      0.0714706000
_diffrn_orient_matrix_UB_22      -0.0908280000
_diffrn_orient_matrix_UB_23      0.0452349000
_diffrn_orient_matrix_UB_31      0.0370672000
_diffrn_orient_matrix_UB_32      -0.0500637000
_diffrn_orient_matrix_UB_33      -0.0831498000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8838
_diffrn_reflns_theta_full        71.71
_diffrn_reflns_theta_max         71.71
_diffrn_reflns_theta_min         4.35
_diffrn_source                   'Nova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    3.140
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3690
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0272
_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/[\s^2^(Fo^2^)+(0.0322P)^2^+1.9920P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0853
_reflns_number_gt                3528
_reflns_number_total             3690
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25629k.txt
_cod_data_source_block           wwt_5.2_111203
_cod_database_code               7152426
_reflns_odcompleteness_completeness 99.02
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98