N,N'-Dioxide/nickel(II)-catalyzed asymmetric Diels-Alder reaction of cyclopentadiene with 2,3-dioxopyrrolidines and 2=alkenoyl pyridines
Yan Lu; Yuhang Zhou; Lili Lin; Haifeng Zheng; Kai Fu; Xiaohua Liu; Xiaoming Feng; Chem.Commun. 52 (2016) 8255–; doi:

data_7119649
_publ_section_title
;
 N,N'-Dioxide/nickel(II)-catalyzed asymmetric Diels-Alder reaction of
 cyclopentadiene with 2,3-dioxopyrrolidines and 2=alkenoyl pyridines
;
_journal_name_full               Chem.Commun.
_journal_page_first              8255
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H20 Cl N O2'
_chemical_formula_sum            'C23 H20 Cl N O2'
_chemical_formula_weight         377.85
_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
_audit_creation_date             2015-11-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-11-24 deposited with the CCDC.
2016-06-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4627(2)
_cell_length_b                   11.1519(3)
_cell_length_c                   18.1676(6)
_cell_measurement_reflns_used    5313
_cell_measurement_temperature    294.39(10)
_cell_measurement_theta_max      72.4690
_cell_measurement_theta_min      3.9550
_cell_volume                     1917.17(9)
_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      294.39(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   23.00   90.00   1.0000    4.2200
omega____ theta____ kappa____ phi______ frames
    -       36.4171 -125.0000  150.0000 67

  2 omega    1.00   75.00   1.0000    4.2200
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000    0.0000 74

  3 omega  -33.00   55.00   1.0000    4.2200
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -38.0000 -150.0000 88

  4 omega   23.00   90.00   1.0000    4.2200
omega____ theta____ kappa____ phi______ frames
    -       36.4171 -125.0000   90.0000 67

  5 omega   18.00  106.00   1.0000    4.2200
omega____ theta____ kappa____ phi______ frames
    -       36.4171   38.0000   30.0000 88

  6 omega   39.00  109.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

  7 omega  100.00  178.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 78

  8 omega   40.00   98.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

  9 omega   38.00   91.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 10 omega   91.00  176.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 85

 11 omega   40.00  135.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 95

 12 omega   40.00   98.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 58

 13 omega   38.00   91.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

 14 omega   38.00  116.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 78

 15 omega   20.00  104.00   1.0000    4.2200
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000  150.0000 84

 16 omega   10.00  104.00   1.0000    4.2200
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000 -120.0000 94
;
_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      0.0829749000
_diffrn_orient_matrix_UB_12      0.0007470000
_diffrn_orient_matrix_UB_13      -0.0729433000
_diffrn_orient_matrix_UB_21      -0.0811855000
_diffrn_orient_matrix_UB_22      0.1127751000
_diffrn_orient_matrix_UB_23      -0.0245828000
_diffrn_orient_matrix_UB_31      0.1141596000
_diffrn_orient_matrix_UB_32      0.0797646000
_diffrn_orient_matrix_UB_33      0.0355744000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10153
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.063
_diffrn_reflns_theta_max         67.063
_diffrn_reflns_theta_min         4.653
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.899
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44016
_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    1.309
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1276 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.010(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3423
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0840P)^2^+0.1760P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1296
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3199
_reflns_number_total             3423
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc03346f2.cif
_cod_data_source_block           fxm-ly-3c1
_cod_original_cell_volume        1917.18(9)
_cod_database_code               7119649
_reflns_odcompleteness_completeness 99.85
_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
2.a Ternary CH refined with riding coordinates:
 C008(H008), C00E(H00E), C00H(H00H)
2.b Secondary CH2 refined with riding coordinates:
 C007(H00A,H00B), C00J(H00D,H00J), C00L(H00L,H00M)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00C), C00F(H00F), C00G(H00G), C00I(H00I), C00K(H00K), C00M(H00N),
 C00N(H00O), C00O(H00P), C00P(H00Q), C00Q(H00R), C00R(H00S)
;
_shelx_res_checksum              58951
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-11-23
_olex2_submission_special_instructions 'No special instructions were received'