#------------------------------------------------------------------------------
#$Date: 2020-11-06 13:33:16 +0100 (vie 06 de nov de 2020) $
#$Revision: 258878 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/12/7241234.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_7241234
loop_
_publ_author_name
'Shen, Jinhui'
'Yu, Aimin'
'Zhang, Lei'
'Meng, Xiangtai'
_publ_section_title
;
 Construction of benzothiophene fused pyrrolidone in water via a
 catalyst-free process and a mechanism study
;
_journal_issue                   20
_journal_name_full               'Green Chemistry'
_journal_page_first              6798
_journal_page_last               6803
_journal_paper_doi               10.1039/D0GC01860K
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C19 H23 N O4 S'
_chemical_formula_sum            'C19 H23 N O4 S'
_chemical_formula_weight         361.44
_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     dual
_audit_creation_date             2019-05-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-28 deposited with the CCDC.	2020-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                108.185(11)
_cell_angle_beta                 106.055(11)
_cell_angle_gamma                109.685(12)
_cell_formula_units_Z            2
_cell_length_a                   9.0842(12)
_cell_length_b                   11.1680(14)
_cell_length_c                   11.3556(13)
_cell_measurement_reflns_used    1374
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7300
_cell_measurement_theta_min      2.7470
_cell_volume                     932.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (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 0.998
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00 106.00   1.00    1.00    --   30.00  54.00 150.00  103
  2  ω     88.00 114.00   1.00    1.00    --   30.00  54.00  30.00   26
  3  ω    -73.00 111.00   1.00    1.00    --   30.00  54.00-120.00  184
  4  ω    -68.00 -34.00   1.00    1.00    --   30.00  54.00  30.00   34
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0011253000
_diffrn_orient_matrix_UB_12      0.0389641000
_diffrn_orient_matrix_UB_13      -0.0388269000
_diffrn_orient_matrix_UB_21      0.0589956000
_diffrn_orient_matrix_UB_22      0.0640079000
_diffrn_orient_matrix_UB_23      0.0606651000
_diffrn_orient_matrix_UB_31      0.0701859000
_diffrn_orient_matrix_UB_32      -0.0087445000
_diffrn_orient_matrix_UB_33      -0.0098454000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8158
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.805
_diffrn_reflns_theta_min         2.569
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         6010
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1322
_refine_ls_R_factor_gt           0.0743
_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/[σ²(Fo²)+(0.1242P)²+0.1997P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2022
_refine_ls_wR_factor_ref         0.2594
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3180
_reflns_number_total             6010
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0gc01860k2.cif
_cod_data_source_block           1_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7241227--7241236.cif.'
_cod_original_cell_volume        932.0(2)
_cod_database_code               7241234
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 99.74
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid bond restraints
 C00H, C00M
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Ternary CH refined with riding coordinates:
 C00D(H00D)
3.b Secondary CH2 refined with riding coordinates:
 C00H(H00B,H00C), C00I(H00F,H00G), C00M(H00M,H00N), C00P(H00U,H00V)
3.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00E(H00E), C00J(H00J), C00K(H00K)
3.d Idealised Me refined as rotating group:
 C00L(H00H,H00I,H00L), C00N(H00O,H00P,H00Q), C00O(H00R,H00S,H00T)
3.e Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_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 1.656
_oxdiff_exptl_absorpt_empirical_full_min 0.608
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.17475(12) 0.90026(8) 0.28273(9) 0.0673(3) Uani 1 1 d . . . . .
O002 O 0.3077(3) 0.6984(2) 0.48874(18) 0.0528(5) Uani 1 1 d . . . . .
H002 H 0.350189 0.773346 0.558089 0.079 Uiso 1 1 calc GR . . . .
O003 O 0.6227(3) 0.94569(19) 0.12843(19) 0.0566(5) Uani 1 1 d . . . . .
O004 O 0.0281(3) 0.44720(19) 0.2304(2) 0.0594(5) Uani 1 1 d . . . . .
N005 N 0.2149(3) 0.5851(2) 0.1694(2) 0.0434(4) Uani 1 1 d . . . . .
O006 O 0.5505(3) 1.0246(2) 0.2999(2) 0.0666(6) Uani 1 1 d . . . . .
C007 C 0.0561(3) 0.7335(2) 0.3944(2) 0.0413(5) Uani 1 1 d . . . . .
C008 C 0.2012(3) 0.7058(2) 0.3763(2) 0.0415(5) Uani 1 1 d . . . . .
C009 C 0.3229(3) 0.7278(2) 0.2133(2) 0.0415(5) Uani 1 1 d . . . . .
C00A C -0.0427(3) 0.6769(3) 0.4546(3) 0.0475(6) Uani 1 1 d . . . . .
H00A H -0.021761 0.615416 0.488222 0.057 Uiso 1 1 calc R . . . .
C00B C 0.1330(3) 0.5618(3) 0.2525(2) 0.0445(5) Uani 1 1 d . . . . .
C00C C 0.0272(4) 0.8266(3) 0.3434(3) 0.0481(6) Uani 1 1 d . . . . .
C00D C 0.3035(3) 0.8143(2) 0.3348(2) 0.0450(5) Uani 1 1 d . . . . .
H00D H 0.416779 0.884845 0.410557 0.054 Uiso 1 1 calc R . . . .
C00E C 0.4223(3) 0.7759(3) 0.1538(3) 0.0476(6) Uani 1 1 d . . . . .
H00E H 0.419428 0.710355 0.077537 0.057 Uiso 1 1 calc R . . . .
C00F C -0.1738(3) 0.7112(3) 0.4653(3) 0.0514(6) Uani 1 1 d . . . . .
C00G C 0.5345(3) 0.9266(3) 0.2036(3) 0.0483(6) Uani 1 1 d . . . . .
C00H C 0.1876(4) 0.4679(3) 0.0470(3) 0.0520(6) Uani 1 1 d . U . . .
H00B H 0.177145 0.495566 -0.026590 0.062 Uiso 1 1 calc R . . . .
H00C H 0.079640 0.385508 0.018037 0.062 Uiso 1 1 calc R . . . .
C00I C 0.7434(4) 1.0902(3) 0.1644(3) 0.0620(7) Uani 1 1 d . . . . .
H00F H 0.823703 1.138582 0.260459 0.074 Uiso 1 1 calc R . . . .
H00G H 0.681438 1.143363 0.147982 0.074 Uiso 1 1 calc R . . . .
C00J C -0.2049(4) 0.8000(3) 0.4097(3) 0.0607(7) Uani 1 1 d . . . . .
H00J H -0.294458 0.821252 0.413841 0.073 Uiso 1 1 calc R . . . .
C00K C -0.1082(4) 0.8573(3) 0.3490(3) 0.0626(8) Uani 1 1 d . . . . .
H00K H -0.132610 0.915714 0.312156 0.075 Uiso 1 1 calc R . . . .
C00L C -0.2763(4) 0.6561(4) 0.5385(4) 0.0718(9) Uani 1 1 d . . . . .
H00H H -0.286583 0.564101 0.526064 0.108 Uiso 1 1 calc GR . . . .
H00I H -0.389407 0.648635 0.501267 0.108 Uiso 1 1 calc GR . . . .
H00L H -0.217799 0.720627 0.634509 0.108 Uiso 1 1 calc GR . . . .
C00M C 0.3326(5) 0.4268(4) 0.0708(3) 0.0674(8) Uani 1 1 d . U . . .
H00M H 0.310499 0.354635 -0.015548 0.081 Uiso 1 1 calc R . . . .
H00N H 0.439928 0.509497 0.099239 0.081 Uiso 1 1 calc R . . . .
C00N C 0.8377(5) 1.0792(4) 0.0770(4) 0.0878(11) Uani 1 1 d . . . . .
H00O H 0.756822 1.030896 -0.017708 0.132 Uiso 1 1 calc GR . . . .
H00P H 0.898757 1.026654 0.094464 0.132 Uiso 1 1 calc GR . . . .
H00Q H 0.918538 1.172779 0.097750 0.132 Uiso 1 1 calc GR . . . .
C00O C 0.5063(6) 0.3354(5) 0.1973(4) 0.0908(12) Uani 1 1 d . . . . .
H00R H 0.481701 0.257219 0.115606 0.136 Uiso 1 1 calc GR . . . .
H00S H 0.519991 0.309193 0.271022 0.136 Uiso 1 1 calc GR . . . .
H00T H 0.611032 0.416314 0.220913 0.136 Uiso 1 1 calc GR . . . .
C00P C 0.3554(6) 0.3733(5) 0.1723(4) 0.0917(12) Uani 1 1 d . . . . .
H00U H 0.249281 0.289145 0.142903 0.110 Uiso 1 1 calc R . . . .
H00V H 0.375184 0.444529 0.258301 0.110 Uiso 1 1 calc R . . . .
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'
N N 0.0061 0.0033 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00C S001 C00D 92.23(11) . . ?
C008 O002 H002 109.5 . . ?
C00G O003 C00I 118.5(2) . . ?
C009 N005 C00H 124.3(2) . . ?
C00B N005 C009 113.61(18) . . ?
C00B N005 C00H 122.1(2) . . ?
C00A C007 C008 126.0(2) . . ?
C00A C007 C00C 120.8(2) . . ?
C00C C007 C008 113.2(2) . . ?
O002 C008 C007 114.49(19) . . ?
O002 C008 C00B 104.68(17) . . ?
O002 C008 C00D 113.3(2) . . ?
C007 C008 C00B 111.7(2) . . ?
C007 C008 C00D 109.18(18) . . ?
C00B C008 C00D 102.81(18) . . ?
N005 C009 C00D 107.8(2) . . ?
C00E C009 N005 124.4(2) . . ?
C00E C009 C00D 127.7(2) . . ?
C007 C00A H00A 119.8 . . ?
C007 C00A C00F 120.4(2) . . ?
C00F C00A H00A 119.8 . . ?
O004 C00B N005 124.8(2) . . ?
O004 C00B C008 126.9(2) . . ?
N005 C00B C008 108.29(19) . . ?
C007 C00C S001 115.17(18) . . ?
C00K C00C S001 125.6(2) . . ?
C00K C00C C007 119.2(2) . . ?
S001 C00D H00D 111.0 . . ?
C008 C00D S001 108.37(16) . . ?
C008 C00D H00D 111.0 . . ?
C009 C00D S001 109.75(17) . . ?
C009 C00D C008 105.68(18) . . ?
C009 C00D H00D 111.0 . . ?
C009 C00E H00E 118.7 . . ?
C009 C00E C00G 122.7(2) . . ?
C00G C00E H00E 118.7 . . ?
C00A C00F C00J 118.0(2) . . ?
C00A C00F C00L 120.7(3) . . ?
C00J C00F C00L 121.3(2) . . ?
O003 C00G C00E 110.8(2) . . ?
O006 C00G O003 122.7(2) . . ?
O006 C00G C00E 126.5(2) . . ?
N005 C00H H00B 109.0 . . ?
N005 C00H H00C 109.0 . . ?
N005 C00H C00M 113.1(2) . . ?
H00B C00H H00C 107.8 . . ?
C00M C00H H00B 109.0 . . ?
C00M C00H H00C 109.0 . . ?
O003 C00I H00F 110.3 . . ?
O003 C00I H00G 110.3 . . ?
O003 C00I C00N 107.1(2) . . ?
H00F C00I H00G 108.5 . . ?
C00N C00I H00F 110.3 . . ?
C00N C00I H00G 110.3 . . ?
C00F C00J H00J 118.7 . . ?
C00K C00J C00F 122.5(2) . . ?
C00K C00J H00J 118.7 . . ?
C00C C00K H00K 120.5 . . ?
C00J C00K C00C 119.0(2) . . ?
C00J C00K H00K 120.5 . . ?
C00F C00L H00H 109.5 . . ?
C00F C00L H00I 109.5 . . ?
C00F C00L H00L 109.5 . . ?
H00H C00L H00I 109.5 . . ?
H00H C00L H00L 109.5 . . ?
H00I C00L H00L 109.5 . . ?
C00H C00M H00M 108.5 . . ?
C00H C00M H00N 108.5 . . ?
H00M C00M H00N 107.5 . . ?
C00P C00M C00H 115.1(3) . . ?
C00P C00M H00M 108.5 . . ?
C00P C00M H00N 108.5 . . ?
C00I C00N H00O 109.5 . . ?
C00I C00N H00P 109.5 . . ?
C00I C00N H00Q 109.5 . . ?
H00O C00N H00P 109.5 . . ?
H00O C00N H00Q 109.5 . . ?
H00P C00N H00Q 109.5 . . ?
H00R C00O H00S 109.5 . . ?
H00R C00O H00T 109.5 . . ?
H00S C00O H00T 109.5 . . ?
C00P C00O H00R 109.5 . . ?
C00P C00O H00S 109.5 . . ?
C00P C00O H00T 109.5 . . ?
C00M C00P C00O 114.3(3) . . ?
C00M C00P H00U 108.7 . . ?
C00M C00P H00V 108.7 . . ?
C00O C00P H00U 108.7 . . ?
C00O C00P H00V 108.7 . . ?
H00U C00P H00V 107.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 C00C 1.751(3) . ?
S001 C00D 1.836(3) . ?
O002 H002 0.8200 . ?
O002 C008 1.417(3) . ?
O003 C00G 1.339(3) . ?
O003 C00I 1.456(3) . ?
O004 C00B 1.206(3) . ?
N005 C009 1.389(3) . ?
N005 C00B 1.387(3) . ?
N005 C00H 1.470(3) . ?
O006 C00G 1.214(3) . ?
C007 C008 1.503(3) . ?
C007 C00A 1.378(3) . ?
C007 C00C 1.401(3) . ?
C008 C00B 1.544(3) . ?
C008 C00D 1.547(3) . ?
C009 C00D 1.511(3) . ?
C009 C00E 1.341(3) . ?
C00A H00A 0.9300 . ?
C00A C00F 1.392(3) . ?
C00C C00K 1.397(4) . ?
C00D H00D 0.9800 . ?
C00E H00E 0.9300 . ?
C00E C00G 1.457(4) . ?
C00F C00J 1.394(4) . ?
C00F C00L 1.515(4) . ?
C00H H00B 0.9700 . ?
C00H H00C 0.9700 . ?
C00H C00M 1.518(4) . ?
C00I H00F 0.9700 . ?
C00I H00G 0.9700 . ?
C00I C00N 1.482(4) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.375(4) . ?
C00K H00K 0.9300 . ?
C00L H00H 0.9600 . ?
C00L H00I 0.9600 . ?
C00L H00L 0.9600 . ?
C00M H00M 0.9700 . ?
C00M H00N 0.9700 . ?
C00M C00P 1.452(5) . ?
C00N H00O 0.9600 . ?
C00N H00P 0.9600 . ?
C00N H00Q 0.9600 . ?
C00O H00R 0.9600 . ?
C00O H00S 0.9600 . ?
C00O H00T 0.9600 . ?
C00O C00P 1.546(5) . ?
C00P H00U 0.9700 . ?
C00P H00V 0.9700 . ?
