Catalytic asymmetric [3 + 3] annulation of cyclopropanes with mercaptoacetaldehyde.
Fu, Xuan; Lin, Lili; Xia, Yong; Zhou, Pengfei; Liu, Xiaohua; Feng, Xiaoming; Organic & biomolecular chemistry 14 (2016) 5914–5917; doi:10.1039/c6ob00948d

data_7155123
_publ_section_title
;
 Catalytic asymmetric [3 + 3] annulation of cyclopropanes with
 mercaptoacetaldehyde.
;
_journal_issue                   25
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5914
_journal_page_last               5917
_journal_paper_doi               10.1039/c6ob00948d
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C18 H16 O S'
_chemical_formula_sum            'C18 H16 O S'
_chemical_formula_weight         280.37
_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             2016-01-12
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-01-12 deposited with the CCDC.
2016-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7389(4)
_cell_length_b                   11.4338(8)
_cell_length_c                   22.2456(18)
_cell_measurement_reflns_used    3974
_cell_measurement_temperature    207(70)
_cell_measurement_theta_max      27.8320
_cell_measurement_theta_min      3.9260
_cell_volume                     1459.70(19)
_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      N~2~
_diffrn_ambient_temperature      207(70)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   -9.00  100.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       25.5845   57.0000  -30.0000 109

  2 omega  -15.00  106.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       25.5845   77.0000  120.0000 121

  3 omega  -15.00  106.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       25.5845   77.0000    0.0000 121

  4 omega   34.00   90.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       25.5845 -178.0000 -180.0000 56
;
_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      -0.0224488000
_diffrn_orient_matrix_UB_12      0.0605683000
_diffrn_orient_matrix_UB_13      0.0037104000
_diffrn_orient_matrix_UB_21      -0.0296763000
_diffrn_orient_matrix_UB_22      0.0043008000
_diffrn_orient_matrix_UB_23      -0.0308901000
_diffrn_orient_matrix_UB_31      -0.1178777000
_diffrn_orient_matrix_UB_32      -0.0124706000
_diffrn_orient_matrix_UB_33      0.0070446000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8673
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.564
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50226
_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    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.6
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 985 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2969
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0560P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1068
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2742
_reflns_number_total             2969
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob00948d2.cif
_cod_data_source_block           fxm-fx-st-bts
_cod_depositor_comments          'Adding full bibliography for 7155123.cif.'
_cod_database_code               7155123
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C005(H005)
2.b Secondary CH2 refined with riding coordinates:
 C006(H00A,H00B), C00C(H00E,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00C), C00B(H00D), C00D(H00G), C00E(H00H), C00F(H00I),
 C00G(H00J), C00H(H00K), C00I(H00L), C00J(H00M), C00K(H00N)
;
_shelx_res_checksum              92185
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-10-29
_olex2_submission_special_instructions 'No special instructions were received'