Asymmetric Formal [3 + 2]-Cycloaddition of Azomethine Imines with Azlactones To Synthesize Bicyclic Pyrazolidinones.
Zhang, Qian; Guo, Songsong; Yang, Jian; Yu, Kunru; Feng, Xiaoming; Lin, Lili; Liu, Xiaohua; Organic letters 19 (2017) 5826–5829; doi:10.1021/acs.orglett.7b02772

data_1547791
_publ_section_title
;
 Asymmetric Formal [3 + 2]-Cycloaddition of Azomethine Imines with
 Azlactones To Synthesize Bicyclic Pyrazolidinones.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5826
_journal_page_last               5829
_journal_paper_doi               10.1021/acs.orglett.7b02772
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H22 Br N3 O3'
_chemical_formula_sum            'C26 H22 Br N3 O3'
_chemical_formula_weight         504.37
_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             2017-03-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3208(4)
_cell_length_b                   12.8006(6)
_cell_length_c                   19.0030(9)
_cell_measurement_reflns_used    6123
_cell_measurement_temperature    290.64(10)
_cell_measurement_theta_max      72.1020
_cell_measurement_theta_min      4.1540
_cell_volume                     2267.28(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.64(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega  -35.00   66.00   1.0000    1.0300
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -19.0000 -180.0000 101

  2 omega    1.00   75.00   1.0000    1.0300
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000 -150.0000 74

  3 omega   10.00  104.00   1.0000    1.0300
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -60.0000 94

  4 omega   23.00   90.00   1.0000    1.0300
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000   30.0000 67

  5 omega   20.00  104.00   1.0000    1.0300
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   60.0000 84

  6 omega    1.00   75.00   1.0000    1.0300
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  120.0000 74

  7 omega   38.00   91.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

  8 omega   38.00  116.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 78

  9 omega   39.00  109.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

 10 omega   38.00   91.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

 11 omega   91.00  176.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 85

 12 omega   39.00  109.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

 13 omega   38.00   91.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

 14 omega   40.00   98.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 58

 15 omega   41.00  116.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -30.0000 75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0563057000
_diffrn_orient_matrix_UB_12      -0.0413925000
_diffrn_orient_matrix_UB_13      -0.0708792000
_diffrn_orient_matrix_UB_21      -0.0542016000
_diffrn_orient_matrix_UB_22      0.1102140000
_diffrn_orient_matrix_UB_23      -0.0188578000
_diffrn_orient_matrix_UB_31      0.1456800000
_diffrn_orient_matrix_UB_32      0.0250118000
_diffrn_orient_matrix_UB_33      -0.0344864000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11569
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.580
_diffrn_reflns_theta_min         4.654
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.749
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_description       plate
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Flack x determined using 1702 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.019(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0870P)^2^+0.1760P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1214
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                4239
_reflns_number_total             4385
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02772_si_001.cif
_cod_data_source_block           fxm-ouji-239-br
_cod_depositor_comments          'Adding full bibliography for 1547791.cif.'
_cod_original_cell_volume        2267.28(19)
_cod_database_code               1547791
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C00C(H00C)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00B), C00M(H00D,H00E), C00O(H00G,H00H)
2.c Aromatic/amide H refined with riding coordinates:
 N007(H007), C00F(H00F), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00N(H00N), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U),
 C00V(H00V), C00W(H00W), C00X(H00X)
;
_olex2_date_sample_data_collection 2017-03-24
_olex2_submission_special_instructions 'No special instructions were received'