Photoinduced cascade cyclization of alkynes with NH4SCN: access to SCN-containing dibenzazepines or dioxodibenzothiazepines
Chen, Shiliu; Yan, Qinqin; Fan, Jie; Gao, Yongjun; Yang, Xiulong; Li, Lijun; Liu, Zhongquan; Li, Zejiang; Green Chemistry 24 (2022) 4742–4747; doi:10.1039/D2GC01276F

data_7244962
_publ_section_title
;
 Photoinduced cascade cyclization of alkynes with NH4SCN: access to
 SCN-containing dibenzazepines or dioxodibenzothiazepines
;
_journal_issue                   12
_journal_name_full               'Green Chemistry'
_journal_page_first              4742
_journal_page_last               4747
_journal_paper_doi               10.1039/D2GC01276F
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C19 H13 F3 N2 O S'
_chemical_formula_sum            'C19 H13 F3 N2 O S'
_chemical_formula_weight         374.37
_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   geom
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc2bmw3z
_audit_creation_date             2021-09-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-04-02 deposited with the CCDC.	2022-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.0140(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5655(3)
_cell_length_b                   25.6875(12)
_cell_length_c                   7.7171(3)
_cell_measurement_reflns_used    2807
_cell_measurement_temperature    170.0
_cell_measurement_theta_max      25.39
_cell_measurement_theta_min      2.41
_cell_volume                     1677.00(12)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.0640
_diffrn_reflns_av_unetI/netI     0.0658
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            12830
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.394
_diffrn_reflns_theta_min         2.408
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1364 before and 0.0517 after correction.
The Ratio of minimum to maximum transmission is 0.9164.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3436
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0504
_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^)+(0.0328P)^2^+1.0933P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1122
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2300
_reflns_number_total             3436
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc01276f2.cif
_cod_data_source_block           gg
_cod_depositor_comments          'Adding full bibliography for 7244962.cif.'
_cod_original_cell_volume        1676.99(12)
_cod_database_code               7244962
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.959
_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:
 C00L(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J),
 C00M(H00M), C00O(H00O)
2.c Idealised Me refined as rotating group:
 C00Q(H00C,H00F,H00K)
;
_shelx_res_checksum              70532
_shelx_hkl_checksum              31005
_olex2_submission_special_instructions 'No special instructions were received'