Asymmetric Synthesis of Spiro-epoxyoxindoles by the Catalytic Darzens Reaction of Isatins with Phenacyl Bromides.
Kuang, Yulong; Lu, Yan; Tang, Yu; Liu, Xiaohua; Lin, Lili; Feng, Xiaoming; Organic letters 16 (2014) 4244–4247; doi:10.1021/ol501941n

data_1517499
_publ_section_title
;
 Asymmetric Synthesis of Spiro-epoxyoxindoles by the Catalytic Darzens
 Reaction of Isatins with Phenacyl Bromides.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4244
_journal_page_last               4247
_journal_paper_doi               10.1021/ol501941n
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C17 H14 Br N O3'
_chemical_formula_sum            'C17 H14 Br N O3'
_chemical_formula_weight         360.20
_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
_audit_creation_date             2014-06-05
_audit_creation_method
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Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6370(3)
_cell_length_b                   9.6961(4)
_cell_length_c                   18.1885(8)
_cell_measurement_reflns_used    1419
_cell_measurement_temperature    143.00(10)
_cell_measurement_theta_max      24.8900
_cell_measurement_theta_min      3.8540
_cell_volume                     1523.20(11)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      143.00(10)
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -18.00   24.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5174  -99.0000  150.0000 84

  2 omega  -51.00   63.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2361  -19.0000  120.0000 228
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0030026000
_diffrn_orient_matrix_UB_12      0.0618285000
_diffrn_orient_matrix_UB_13      -0.0207423000
_diffrn_orient_matrix_UB_21      -0.0336667000
_diffrn_orient_matrix_UB_22      -0.0346285000
_diffrn_orient_matrix_UB_23      -0.0304512000
_diffrn_orient_matrix_UB_31      -0.0748513000
_diffrn_orient_matrix_UB_32      0.0180412000
_diffrn_orient_matrix_UB_33      0.0128135000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4608
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.071
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.710
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_description
;
;
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.763
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Flack x determined using 930 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.500(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3053
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+0.7062P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1247
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                2616
_reflns_number_total             3053
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol501941n_si_001.cif
_cod_data_source_block           1
_cod_database_code               1517499
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         c12h14n2o3br1
_shelx_estimated_absorpt_t_max   0.497
_shelx_estimated_absorpt_t_min   0.451
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2A)
;
_shelx_res_checksum              34753
_shelx_hkl_checksum              64384