The asymmetric synthesis of multisubstituted diquinanes via the domino reaction of electron-deficient enynes
Yao, Qian; Lin, Lili; Zhang, Hang; Yu, Han; Xiong, Qian; Liu, Xiaohua; Feng, Xiaoming; Organic Chemistry Frontiers 4 (2017) 2012–; doi:10.1039/C7QO00408G

data_1553815
_publ_section_title
;
 The asymmetric synthesis of multisubstituted diquinanes via the domino
 reaction of electron-deficient enynes
;
_journal_issue                   10
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2012
_journal_paper_doi               10.1039/C7QO00408G
_journal_volume                  4
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H23 Cl O7'
_chemical_formula_sum            'C23 H23 Cl O7'
_chemical_formula_weight         446.86
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-10-19
_audit_creation_method
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Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2016-11-30 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.82668(15)
_cell_length_b                   9.4989(2)
_cell_length_c                   34.5079(10)
_cell_measurement_reflns_used    4641
_cell_measurement_temperature    293.49(15)
_cell_measurement_theta_max      72.4700
_cell_measurement_theta_min      3.8540
_cell_volume                     2237.70(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
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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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      293.49(15)
_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 0.999
_diffrn_measurement_details
;
  1 omega   10.00  104.00   1.0000    1.3750
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  150.0000 94

  2 omega   20.00  104.00   1.0000    1.3750
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  150.0000 84

  3 omega  -31.00   63.00   1.0000    1.3750
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000  -30.0000 94

  4 omega  -31.00   53.00   1.0000    1.3750
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000    0.0000 84

  5 omega   10.00  104.00   1.0000    1.3750
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   90.0000 94

  6 omega   39.00  109.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 70

  7 omega   38.00   91.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

  8 omega   40.00   98.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

  9 omega   40.00   98.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

 10 omega   38.00   91.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 11 omega   38.00  116.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 78

 12 omega   39.00  177.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  -60.0000 138

 13 omega  -33.00   55.00   1.0000    1.3750
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000  150.0000 88

 14 omega    1.00   75.00   1.0000    1.3750
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  120.0000 74

 15 omega   20.00   77.00   1.0000    1.3750
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -120.0000 57

 16 omega   17.00  105.00   1.0000    1.3750
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000  -30.0000 88
;
_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      -0.0335980000
_diffrn_orient_matrix_UB_12      -0.0431330000
_diffrn_orient_matrix_UB_13      0.0425111000
_diffrn_orient_matrix_UB_21      -0.0463296000
_diffrn_orient_matrix_UB_22      0.1541115000
_diffrn_orient_matrix_UB_23      0.0104321000
_diffrn_orient_matrix_UB_31      -0.2183538000
_diffrn_orient_matrix_UB_32      -0.0260708000
_diffrn_orient_matrix_UB_33      -0.0087765000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            11954
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.074
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         5.127
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.868
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42940
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1356 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1004P)^2^+0.2458P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1492
_refine_ls_wR_factor_ref         0.1553
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3621
_reflns_number_total             3976
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00408g2.cif
_cod_data_source_block           1
_cod_original_cell_volume        2237.69(10)
_cod_database_code               1553815
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              43608
_shelx_hkl_checksum              75048
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'