Solvent-Controlled Switchable Domino Reactions of MBH Carbonate: Synthesis of Benzothiophene Fused α-Pyran, 2,3-Dihydrooxepine, and Oxatricyclodecene Derivatives.
Jia, Jiru; Yu, Aimin; Ma, Shanshan; Zhang, Youquan; Li, Ke; Meng, Xiangtai; Organic letters 19 (2017) 6084–6087; doi:10.1021/acs.orglett.7b02916

data_1548609
_publ_section_title
;
 Solvent-Controlled Switchable Domino Reactions of MBH Carbonate:
 Synthesis of Benzothiophene Fused \a-Pyran, 2,3-Dihydrooxepine, and
 Oxatricyclodecene Derivatives.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              6084
_journal_page_last               6087
_journal_paper_doi               10.1021/acs.orglett.7b02916
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C24 H21 Cl O5 S'
_chemical_formula_sum            'C24 H21 Cl O5 S'
_chemical_formula_weight         456.92
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                79.965(14)
_cell_angle_beta                 74.188(18)
_cell_angle_gamma                89.590(15)
_cell_formula_units_Z            2
_cell_length_a                   8.680(2)
_cell_length_b                   10.6240(15)
_cell_length_c                   12.798(2)
_cell_measurement_reflns_used    875
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.1380
_cell_measurement_theta_min      1.9610
_cell_volume                     1117.1(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.40t (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.40t (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.40t (Rigaku OD, 2015)'
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -75.00 120.00   1.00   15.00    --   30.00  54.00 120.00  195
  2  \w    -75.00  30.00   1.00   15.00    --   30.00  54.00 240.00  105
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0165258000
_diffrn_orient_matrix_UB_12      0.0666611000
_diffrn_orient_matrix_UB_13      -0.0187084000
_diffrn_orient_matrix_UB_21      0.0752643000
_diffrn_orient_matrix_UB_22      -0.0060393000
_diffrn_orient_matrix_UB_23      0.0117486000
_diffrn_orient_matrix_UB_31      0.0358912000
_diffrn_orient_matrix_UB_32      -0.0111870000
_diffrn_orient_matrix_UB_33      -0.0542210000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.1368
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5414
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         1.681
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.40t (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1710
_refine_ls_R_factor_gt           0.0740
_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^)+(0.0918P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1708
_refine_ls_wR_factor_ref         0.2464
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1907
_reflns_number_total             3935
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02916_si_005.cif
_cod_data_source_block           3
_cod_original_cell_volume        1117.2(4)
_cod_database_code               1548609
_reflns_odcompleteness_completeness 82.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.87
_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 Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4), C18(H18), C19(H19), C3(H3), C22(H22), C21(H21)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C1(H1A,H1B,H1C), C24(H24A,H24B,H24C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              50866
_shelx_hkl_checksum              13995
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.509
_oxdiff_exptl_absorpt_empirical_full_min 0.800