Solvent-Controlled, Tunable Hydrosulfonylation of 3-Cyclopropylideneprop-2-en-1-ones.
Miao, Maozhong; Luo, Yi; Xu, Huaping; Chen, Zhengkai; Xu, Jianfeng; Ren, Hongjun; Organic letters 18 (2016) 4292–4295; doi:10.1021/acs.orglett.6b02047

data_1555679
_publ_section_title
;
 Solvent-Controlled, Tunable Hydrosulfonylation of
 3-Cyclopropylideneprop-2-en-1-ones.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4292
_journal_page_last               4295
_journal_paper_doi               10.1021/acs.orglett.6b02047
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C24 H19 Cl O3 S'
_chemical_formula_sum            'C24 H19 Cl O3 S'
_chemical_formula_weight         422.91
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-09-29
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                73.509(7)
_cell_angle_beta                 81.064(6)
_cell_angle_gamma                73.991(6)
_cell_formula_units_Z            2
_cell_length_a                   5.9791(4)
_cell_length_b                   10.7506(9)
_cell_length_c                   17.3037(15)
_cell_measurement_reflns_used    1765
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5232
_cell_measurement_theta_min      3.2618
_cell_volume                     1021.56(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0339046000
_diffrn_orient_matrix_UB_12      0.0344382000
_diffrn_orient_matrix_UB_13      0.0309824000
_diffrn_orient_matrix_UB_21      0.0048450000
_diffrn_orient_matrix_UB_22      -0.0617813000
_diffrn_orient_matrix_UB_23      0.0294159000
_diffrn_orient_matrix_UB_31      0.1190207000
_diffrn_orient_matrix_UB_32      -0.0057369000
_diffrn_orient_matrix_UB_33      0.0038969000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6423
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.56
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.312
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3720
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0351P)^2^+0.1393P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.1084
_reflns_number_gt                2683
_reflns_number_total             3720
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b02047_si_002.cif
_cod_data_source_block           150929_ly4_59
_cod_original_cell_volume        1021.56(14)
_cod_database_code               1555679
_chemical_oxdiff_formula         'c10 h10 n2 o8 s1 Cl1'
_reflns_odcompleteness_completeness 99.50
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C20(H20), C21(H21), C23(H23), C24(H24)
;