The N,N'-dioxide/Ni(ii)-catalyzed asymmetric inverse-electron-demand hetero-Diels-Alder reaction of methyleneindolinones with hetero-substituted alkenes.
Zhou, Yuhang; Lin, Lili; Yin, Chengkai; Wang, Zhengmeng; Liu, Xiaohua; Feng, Xiaoming; Chemical communications (Cambridge, England) 51 (2015) 11689–11692; doi:10.1039/c5cc04245c

data_7117447
_publ_section_title
;
 The N,N'-dioxide/Ni(ii)-catalyzed asymmetric inverse-electron-demand
 hetero-Diels-Alder reaction of methyleneindolinones with
 hetero-substituted alkenes.
;
_journal_issue                   58
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11689
_journal_page_last               11692
_journal_paper_doi               10.1039/c5cc04245c
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C22 H29 N O6'
_chemical_formula_sum            'C22 H29 N O6'
_chemical_formula_weight         403.46
_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             2015-01-16
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_audit_update_record
;
2015-03-27 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.41470(8)
_cell_length_b                   11.96874(11)
_cell_length_c                   21.5473(2)
_cell_measurement_reflns_used    8079
_cell_measurement_temperature    121(2)
_cell_measurement_theta_max      72.5170
_cell_measurement_theta_min      4.2210
_cell_volume                     2170.10(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      121(2)
_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 0.992
_diffrn_measurement_details
;
  1 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000  150.0000 84

  2 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000  -30.0000 74

  3 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000  -30.0000 94

  4 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000  120.0000 74

  5 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421 -125.0000  120.0000 67

  6 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  -60.0000 84

  7 omega   40.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

  8 omega   39.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

  9 omega   39.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 70

 10 omega   40.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

 11 omega   40.00  135.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 95

 12 omega   40.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

 13 omega   39.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000 -150.0000 138

 14 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000 -150.0000 84

 15 omega   20.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000   60.0000 39

 16 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  120.0000 84
;
_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      0.0386772000
_diffrn_orient_matrix_UB_12      -0.0099764000
_diffrn_orient_matrix_UB_13      -0.0696567000
_diffrn_orient_matrix_UB_21      -0.1637810000
_diffrn_orient_matrix_UB_22      -0.0536611000
_diffrn_orient_matrix_UB_23      -0.0115249000
_diffrn_orient_matrix_UB_31      -0.0719446000
_diffrn_orient_matrix_UB_32      0.1166268000
_diffrn_orient_matrix_UB_33      -0.0112345000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12207
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.703
_diffrn_reflns_theta_min         4.225
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.235
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1723 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4236
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0914P)^2^+0.2988P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1213
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                4155
_reflns_number_total             4236
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc04245c2.cif
_cod_data_source_block           fxm-zyh-4d-120k
_cod_database_code               7117447
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H00E(0.032) H00F(0.03) H00G(0.026) H00H(0.039) H00I(0.032)
 H00K(0.038) H00A(0.03) H00B(0.03) H00C(0.052) H00D(0.052) H00J(0.052)
 H00L(0.052) H00M(0.052) H00N(0.052) H00O(0.055) H00P(0.055) H00Q(0.055)
 H00R(0.044) H00S(0.058) H00T(0.058) H00U(0.058) H00V(0.058) H00W(0.058)
 H00X(0.088) H00Y(0.088) H(0.088) H00Z(0.112) HA(0.112) HB(0.112)
 Fixed X: H00E(0.6384) H00F(0.3483) H00G(0.4364) H00H(0.6771) H00I(0.2057)
 H00K(0.536) H00A(0.349) H00B(0.2201) H00C(0.9431) H00D(0.8769) H00J(0.9119)
 H00L(0.0098) H00M(-0.1328) H00N(0.0302) H00O(-0.2175) H00P(-0.2982) H00Q(-
 0.1446) H00R(0.6517) H00S(-0.11) H00T(-0.2689) H00U(-0.2235) H00V(0.4118)
 H00W(0.3181) H00X(0.5484) H00Y(0.6473) H(0.4611) H00Z(0.4713) HA(0.6568)
 HB(0.5763)
 Fixed Y: H00E(0.7742) H00F(0.4861) H00G(0.8215) H00H(0.7307) H00I(0.6104)
 H00K(0.5891) H00A(0.7752) H00B(0.773) H00C(0.6412) H00D(0.6537) H00J(0.7603)
 H00L(0.2454) H00M(0.2048) H00N(0.2348) H00O(0.4945) H00P(0.3768) H00Q(0.4033)
 H00R(0.4451) H00S(0.3772) H00T(0.3373) H00U(0.4644) H00V(0.4058) H00W(0.4389)
 H00X(0.5621) H00Y(0.4658) H(0.4605) H00Z(0.2705) HA(0.2789) HB(0.2597)
 Fixed Z: H00E(0.2392) H00F(0.144) H00G(0.349) H00H(0.1358) H00I(0.4647)
 H00K(0.0887) H00A(0.4546) H00B(0.4018) H00C(0.3634) H00D(0.431) H00J(0.391)
 H00L(0.2443) H00M(0.2854) H00N(0.3164) H00O(0.2436) H00P(0.2384) H00Q(0.1999)
 H00R(0.483) H00S(0.3863) H00T(0.3554) H00U(0.355) H00V(0.4299) H00W(0.4903)
 H00X(0.5594) H00Y(0.59) H(0.5901) H00Z(0.5354) HA(0.5403) HB(0.4756)
;
_shelx_res_checksum              66218
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'