Construction of benzothiophene fused pyrrolidone in water via a catalyst-free process and a mechanism study
Shen, Jinhui; Yu, Aimin; Zhang, Lei; Meng, Xiangtai; Green Chemistry 22 (2020) 6798–6803; doi:10.1039/D0GC01860K

data_7241231
_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         'C16 H19 N O2 S'
_chemical_formula_sum            'C16 H19 N O2 S'
_chemical_formula_weight         289.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-12-15
_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                90
_cell_angle_beta                 100.520(6)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   12.239(5)
_cell_length_b                   19.008(7)
_cell_length_c                   20.975(8)
_cell_measurement_reflns_used    2789
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.94
_cell_measurement_theta_min      2.35
_cell_volume                     4798(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0844
_diffrn_reflns_av_unetI/netI     0.1164
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22763
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         2.003
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0669 before and 0.0446 after correction.
The Ratio of minimum to maximum transmission is 0.8625.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_description       block
_exptl_crystal_F_000             1848
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     563
_refine_ls_number_reflns         8195
_refine_ls_number_restraints     1636
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.2310
_refine_ls_R_factor_gt           0.1242
_refine_ls_shift/su_max          0.059
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3124
_refine_ls_wR_factor_ref         0.3852
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3449
_reflns_number_total             8195
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc01860k2.cif
_cod_data_source_block           11_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7241227--7241236.cif.'
_cod_database_code               7241231
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C15-C16 = C47-C48A
 1.53 with sigma of 0.01
3. Rigid bond restraints
 S1, C5, C45, C47
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 3.8A with sigma of 0.01 and sigma
for terminal atoms of 0.02
Uanis(C15) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(H46C)=Sof(H46D)=Sof(H46E)=Sof(H47D)=Sof(H47E)=Sof(C48A)=Sof(H48D)=
 Sof(H48E)=Sof(H48F)=1-FVAR(1)
 Sof(H46A)=Sof(H46B)=Sof(H47A)=Sof(H47B)=Sof(H47C)=Sof(C48)=Sof(H48A)=
 Sof(H48B)=Sof(H48C)=FVAR(1)
6.a Riding coordinates:
 C47(H47A,H47B,H47C), C47(H47D,H47E), C48(H48A,H48B,H48C)
6.b Ternary CH refined with riding coordinates:
 C45(H45), C29(H29), C13(H13)
6.c Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C46(H46A,H46B), C15(H15A,H15B)
6.d Aromatic/amide H refined with riding coordinates:
 N3(H3), N2(H2), N1(H1), C23(H23), C39(H39), C36(H36), C35(H35), C19(H19),
 C4(H4), C20(H20), C7(H7), C3(H3A)
6.e Idealised Me refined as rotating group:
 C43(H43A,H43B,H43C), C27(H27A,H27B,H27C), C17(H17A,H17B,H17C), C33(H33A,H33B,
 H33C), C30(H30A,H30B,H30C), C46(H46C,H46D,H46E), C11(H11A,H11B,H11C), C1(H1A,
 H1B,H1C), C32(H32A,H32B,H32C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C),
 C48A(H48D,H48E,H48F)
;
_shelx_res_checksum              82244
_olex2_submission_special_instructions 'No special instructions were received'