Lewis acid catalyzed asymmetric [4+2] cycloaddition of cyclobutenones to synthesize α,β-unsaturated δ-lactones.
Yao, Qian; Yu, Han; Zhang, Hang; Dong, Shunxi; Chang, Fenzhen; Lin, Lili; Liu, Xiaohua; Feng, Xiaoming; Chemical communications (Cambridge, England) 54 (2018) 3375–3378; doi:10.1039/C8CC01040D

data_7121376
_publ_section_title
;
 Lewis acid catalyzed asymmetric [4+2] cycloaddition of cyclobutenones to
 synthesize \a,\b-unsaturated \d-lactones.
;
_journal_issue                   27
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3375
_journal_page_last               3378
_journal_paper_doi               10.1039/C8CC01040D
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H19 Cl O4'
_chemical_formula_sum            'C22 H19 Cl O4'
_chemical_formula_weight         382.82
_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             2017-04-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-07-21 deposited with the CCDC.
2018-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.31147(16)
_cell_length_b                   13.7958(4)
_cell_length_c                   19.1823(5)
_cell_measurement_reflns_used    3746
_cell_measurement_temperature    295.0(7)
_cell_measurement_theta_max      72.0470
_cell_measurement_theta_min      6.8190
_cell_volume                     1934.87(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      295.0(7)
_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    1.00   75.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000 -120.0000 74

  2 omega   17.00  105.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000  -30.0000 88

  3 omega  -31.00   63.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000  120.0000 94

  4 omega  -31.00   63.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000   30.0000 94

  5 omega  -35.00   66.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -19.0000  150.0000 101

  6 omega  100.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 78

  7 omega   38.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

  8 omega   38.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

  9 omega   39.00  109.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 70

 10 omega   91.00  176.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 85

 11 omega   91.00  176.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 85

 12 omega   39.00  109.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

 13 omega   38.00  116.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 78

 14 omega   38.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

 15 omega   90.00  165.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 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      0.0348812000
_diffrn_orient_matrix_UB_12      -0.1017589000
_diffrn_orient_matrix_UB_13      0.0303321000
_diffrn_orient_matrix_UB_21      -0.0634452000
_diffrn_orient_matrix_UB_22      0.0354853000
_diffrn_orient_matrix_UB_23      0.0722220000
_diffrn_orient_matrix_UB_31      -0.1977277000
_diffrn_orient_matrix_UB_32      -0.0294004000
_diffrn_orient_matrix_UB_33      -0.0178320000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10758
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.532
_diffrn_reflns_theta_min         4.610
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.953
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68593
_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    1.314
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 1313 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3748
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0587
_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^)+(0.1050P)^2^+0.1540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.1587
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                3469
_reflns_number_total             3748
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc01040d2.cif
_cod_data_source_block           fxm-c-vtz-4me
_cod_depositor_comments          'Adding full bibliography for 7121376.cif.'
_cod_original_cell_volume        1934.87(8)
_cod_database_code               7121376
_shelx_shelxl_version_number     2014/7
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00C(H00C)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00P(H00P), C00Q(H00Q)
2.c Idealised Me refined as rotating group:
 C00O(H00A,H00B,H00E), C00R(H00I,H00O,H00R)
;
_olex2_date_sample_data_collection 2017-04-26
_olex2_submission_special_instructions 'No special instructions were received'