A chiral scandium-complex-catalyzed asymmetric inverse-electron-demand oxa-Diels-Alder reaction of o-quinone methides with fulvenes.
Zhang, Jianlin; Lin, Lili; He, Changqiang; Xiong, Qian; Liu, Xiaohua; Feng, Xiaoming; Chemical communications (Cambridge, England) 54 (2017) 74–77; doi:10.1039/c7cc08124c

data_7120957
_publ_section_title
;
 A chiral scandium-complex-catalyzed asymmetric inverse-electron-demand
 oxa-Diels-Alder reaction of o-quinone methides with fulvenes.
;
_journal_issue                   1
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              74
_journal_page_last               77
_journal_paper_doi               10.1039/c7cc08124c
_journal_volume                  54
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C27 H21 Br O4'
_chemical_formula_sum            'C27 H21 Br O4'
_chemical_formula_weight         489.35
_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             2017-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-08-17 deposited with the CCDC.
2017-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4251(5)
_cell_length_b                   12.4732(4)
_cell_length_c                   14.0656(5)
_cell_measurement_reflns_used    2786
_cell_measurement_temperature    290.64(10)
_cell_measurement_theta_max      71.8370
_cell_measurement_theta_min      4.7410
_cell_volume                     2179.90(14)
_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 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
  1 omega    1.00   75.00   1.0000    2.6550
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000 -180.0000 74

  2 omega  -33.00   55.00   1.0000    2.6550
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -38.0000   90.0000 88

  3 omega  -31.00   53.00   1.0000    2.6550
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000   30.0000 84

  4 omega   18.00  106.00   1.0000    2.6550
omega____ theta____ kappa____ phi______ frames
    -       36.5421   38.0000  -90.0000 88

  5 omega   39.00  109.00   1.0000   10.6150
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

  6 omega   90.00  175.00   1.0000   10.6150
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 85

  7 omega   39.00  109.00   1.0000   10.6150
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

  8 omega   38.00   91.00   1.0000   10.6150
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

  9 omega   38.00   84.00   1.0000   10.6150
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 46

 10 omega   41.00   74.00   1.0000   10.6150
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 33
;
_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      -0.0039487000
_diffrn_orient_matrix_UB_12      0.0950251000
_diffrn_orient_matrix_UB_13      -0.0698216000
_diffrn_orient_matrix_UB_21      -0.0167973000
_diffrn_orient_matrix_UB_22      -0.0784512000
_diffrn_orient_matrix_UB_23      -0.0833375000
_diffrn_orient_matrix_UB_31      -0.1227681000
_diffrn_orient_matrix_UB_32      0.0076406000
_diffrn_orient_matrix_UB_33      0.0137053000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6938
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.583
_diffrn_reflns_theta_min         4.749
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.836
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48632
_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    1.491
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.239
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.128
_refine_ls_abs_structure_details
;
 Flack x determined using 1261 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.028(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0695
_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^)+(0.1343P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1835
_refine_ls_wR_factor_ref         0.1938
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.925
_reflns_Friedel_fraction_max     0.871
_reflns_number_gt                3571
_reflns_number_total             4038
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc08124c2.cif
_cod_data_source_block           exp_3304
_cod_depositor_comments          'Adding full bibliography for 7120957.cif.'
_cod_database_code               7120957
_reflns_odcompleteness_completeness 99.73
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C007(H007), C00J(H00J), C00N(H00N)
2.b Secondary CH2 refined with riding coordinates:
 C00S(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00F(H00F), C00H(H00H), C00I(H00I), C00K(H00K),
 C00L(H00L), C00M(H00M), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00U(H00U)
2.d Idealised Me refined as rotating group:
 C00W(H00E,H00G,H00S)
;
_shelx_res_checksum              69207
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2017-03-21
_olex2_submission_special_instructions 'No special instructions were received'