Ring-opening/annulation reaction of cyclopropyl ethanols: concise access to thiophene aldehydes via C–S bond formation
Wang, Ting; An, Zhenyu; Qi, Zhenjie; Zhuang, Daijiao; Chang, Aosheng; Yang, Yunxia; Yan, Rulong; Organic Chemistry Frontiers 6 (2019) 3705–; doi:10.1039/C9QO01014A

data_1555164
_publ_section_title
;
 Ring-opening/annulation reaction of cyclopropyl ethanols: concise access
 to thiophene aldehydes via C--S bond formation
;
_journal_issue                   21
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3705
_journal_paper_doi               10.1039/C9QO01014A
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C11 H6 Cl2 O S'
_chemical_formula_sum            'C11 H6 Cl2 O S'
_chemical_formula_weight         257.12
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-09-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-02 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6812(11)
_cell_length_b                   6.6839(10)
_cell_length_c                   13.6312(10)
_cell_measurement_reflns_used    499
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.4280
_cell_measurement_theta_min      3.8180
_cell_volume                     1064.3(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -19.00   20.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -99.0000  150.0000 26

  2 omega   46.00   91.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000 -180.0000 30

  3 omega  -19.00   44.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000 -180.0000 42
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0592448000
_diffrn_orient_matrix_UB_12      -0.0040634000
_diffrn_orient_matrix_UB_13      0.0113369000
_diffrn_orient_matrix_UB_21      0.0129225000
_diffrn_orient_matrix_UB_22      0.0445638000
_diffrn_orient_matrix_UB_23      -0.0458732000
_diffrn_orient_matrix_UB_31      -0.0035360000
_diffrn_orient_matrix_UB_32      0.0962467000
_diffrn_orient_matrix_UB_33      0.0217272000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2354
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.39
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.771
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0459
_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^)+(0.0479P)^2^+0.1696P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1271
_reflns_number_gt                763
_reflns_number_total             1140
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9qo01014a2.cif
_cod_data_source_block           wangting_0912
_cod_database_code               1555164
_reflns_odcompleteness_completeness 99.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C11(H11), C5(H5), C7(H7), C10(H10), C1(H1)
;
_olex2_date_sample_data_collection 2018-09-12
_olex2_submission_special_instructions 'No special instructions were received'