#------------------------------------------------------------------------------
#$Date: 2019-11-24 15:32:38 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238360 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/51/1555164.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1555164
loop_
_publ_author_name
'Wang, Ting'
'An, Zhenyu'
'Qi, Zhenjie'
'Zhuang, Daijiao'
'Chang, Aosheng'
'Yang, Yunxia'
'Yan, Rulong'
_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
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -19.00   20.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -99.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega   46.00   91.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
  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       'ω 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/[σ²(Fo²)+(0.0479P)²+0.1696P] where P=(Fo²+2Fc²)/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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z+1/2'
4 '-x, y+1/2, -z'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z-1/2'
8 'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
S1 S 0.91876(11) 0.2500 0.30328(8) 0.0685(5) Uani 1 d 2 S T P
Cl1 Cl 1.52282(10) 0.2500 0.64752(10) 0.0774(5) Uani 1 d 2 S T P
Cl2 Cl 1.29326(10) 0.2500 0.76796(8) 0.0820(5) Uani 1 d 2 S T P
C8 C 1.2913(3) 0.2500 0.6416(3) 0.0457(10) Uani 1 d 2 S T P
C4 C 1.0696(3) 0.2500 0.4415(3) 0.0410(9) Uani 1 d 2 S T P
C3 C 0.9600(3) 0.2500 0.4854(3) 0.0455(10) Uani 1 d 2 S T P
H3 H 0.9498 0.2500 0.5531 0.055 Uiso 1 calc 2 RS T P
C11 C 1.2832(4) 0.2500 0.4414(3) 0.0616(13) Uani 1 d 2 S T P
H11 H 1.2815 0.2500 0.3732 0.074 Uiso 1 calc 2 RS T P
C5 C 1.0570(4) 0.2500 0.3412(3) 0.0584(12) Uani 1 d 2 S T P
H5 H 1.1187 0.2500 0.2981 0.070 Uiso 1 calc 2 RS T P
C7 C 1.1861(3) 0.2500 0.5940(3) 0.0430(10) Uani 1 d 2 S T P
H7 H 1.1188 0.2500 0.6305 0.052 Uiso 1 calc 2 RS T P
C9 C 1.3921(3) 0.2500 0.5893(3) 0.0519(11) Uani 1 d 2 S T P
C6 C 1.1809(3) 0.2500 0.4920(3) 0.0432(9) Uani 1 d 2 S T P
C10 C 1.3878(4) 0.2500 0.4883(4) 0.0659(13) Uani 1 d 2 S T P
H10 H 1.4551 0.2500 0.4518 0.079 Uiso 1 calc 2 RS T P
C2 C 0.8709(3) 0.2500 0.4218(3) 0.0448(10) Uani 1 d 2 S T P
O1 O 0.6745(3) 0.2500 0.3823(2) 0.0703(10) Uani 1 d 2 S T P
C1 C 0.7497(4) 0.2500 0.4424(4) 0.0575(12) Uani 1 d 2 S T P
H1 H 0.7279 0.2500 0.5080 0.069 Uiso 1 calc 2 RS T P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 S1 C2 91.3(2)
C7 C8 Cl2 118.6(3)
C9 C8 Cl2 120.4(3)
C9 C8 C7 121.0(4)
C3 C4 C6 127.0(3)
C5 C4 C3 108.9(4)
C5 C4 C6 124.1(4)
C4 C3 H3 122.5
C2 C3 C4 115.1(4)
C2 C3 H3 122.5
C6 C11 H11 118.8
C10 C11 H11 118.8
C10 C11 C6 122.4(4)
S1 C5 H5 123.0
C4 C5 S1 113.9(3)
C4 C5 H5 123.0
C8 C7 H7 119.8
C6 C7 C8 120.3(4)
C6 C7 H7 119.8
C8 C9 Cl1 121.4(3)
C8 C9 C10 119.1(4)
C10 C9 Cl1 119.5(3)
C11 C6 C4 122.0(4)
C11 C6 C7 117.5(4)
C7 C6 C4 120.4(4)
C11 C10 H10 120.2
C9 C10 C11 119.7(4)
C9 C10 H10 120.2
C3 C2 S1 110.7(3)
C3 C2 C1 129.0(4)
C1 C2 S1 120.3(3)
C2 C1 H1 117.1
O1 C1 C2 125.7(5)
O1 C1 H1 117.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C5 1.695(5)
S1 C2 1.710(4)
Cl1 C9 1.721(4)
Cl2 C8 1.723(4)
C8 C7 1.390(5)
C8 C9 1.376(6)
C4 C3 1.413(5)
C4 C5 1.375(6)
C4 C6 1.472(5)
C3 H3 0.9300
C3 C2 1.356(5)
C11 H11 0.9300
C11 C6 1.380(5)
C11 C10 1.379(6)
C5 H5 0.9300
C7 H7 0.9300
C7 C6 1.391(5)
C9 C10 1.379(6)
C10 H10 0.9300
C2 C1 1.443(6)
O1 C1 1.201(5)
C1 H1 0.9300
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
S1 C2 C1 O1 0.0
Cl1 C9 C10 C11 180.0
Cl2 C8 C7 C6 180.0
Cl2 C8 C9 Cl1 0.0
Cl2 C8 C9 C10 180.0
C8 C7 C6 C4 180.0
C8 C7 C6 C11 0.000(1)
C8 C9 C10 C11 0.000(1)
C4 C3 C2 S1 0.0
C4 C3 C2 C1 180.0
C3 C4 C5 S1 0.0
C3 C4 C6 C11 180.0
C3 C4 C6 C7 0.0
C3 C2 C1 O1 180.0
C5 S1 C2 C3 0.0
C5 S1 C2 C1 180.0
C5 C4 C3 C2 0.0
C5 C4 C6 C11 0.0
C5 C4 C6 C7 180.0
C7 C8 C9 Cl1 180.0
C7 C8 C9 C10 0.000(1)
C9 C8 C7 C6 0.0
C6 C4 C3 C2 180.0
C6 C4 C5 S1 180.0
C6 C11 C10 C9 0.0
C10 C11 C6 C4 180.0
C10 C11 C6 C7 0.0
C2 S1 C5 C4 0.0
