Synthesis of thiocyanato-containing phenanthrenes and dihydronaphthalenes <i>via</i> Lewis acid-activated tandem electrophilic thiocyanation/carbocyclization of alkynes.
Gao, Yong; Hua, Ruirui; Yin, Hongquan; Chen, Fu-Xue; Organic & biomolecular chemistry 21 (2023) 2417–2422; doi:10.1039/d3ob00001j

data_7159214
_publ_section_title
;
 Synthesis of thiocyanato-containing phenanthrenes and dihydronaphthalenes
 <i>via</i> Lewis acid-activated tandem electrophilic
 thiocyanation/carbocyclization of alkynes.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2417
_journal_page_last               2422
_journal_paper_doi               10.1039/d3ob00001j
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C21 H12 F N S'
_chemical_formula_sum            'C21 H12 F N S'
_chemical_formula_weight         329.38
_chemical_name_systematic        1
_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
_audit_creation_date             2022-08-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-09-30 deposited with the CCDC.	2023-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.6730(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.38450(10)
_cell_length_b                   16.89920(10)
_cell_length_c                   8.13090(10)
_cell_measurement_reflns_used    9181
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.9110
_cell_measurement_theta_min      3.8850
_cell_volume                     1562.59(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w      7.00  63.00   0.50    0.50    --   42.30 -82.00-180.00  112
  2  \w     68.00 132.00   0.50    0.50    --   42.30  54.00  30.00  128
  3  \w     13.00  57.00   0.50    0.50    --   42.30 -82.00-120.00   88
  4  \w      5.00  70.00   0.50    0.50    --   42.30 -82.00 -60.00  130
  5  \w     17.00  66.00   0.50    0.50    --   42.30  77.00  60.00   98
  6  \w     63.00 126.00   0.50    0.50    --   42.30  54.00 150.00  126
  7  \w    -36.00   7.00   0.50    0.50    --   42.30 -77.00 150.00   86
  8  \w     19.00  54.00   0.50    0.50    --   42.30  54.00  30.00   70
  9  \w     24.00  74.00   0.50    0.50    --   42.30  65.00-180.00  100
 10  \w    -42.00  23.00   0.50    0.50    --   42.30 -77.00 -60.00  130
 11  \w     11.00  65.00   0.50    0.50    --   42.30 -82.00  90.00  108
 12  \w    -30.00  -5.00   0.50    0.50    --   42.30 -82.00  90.00   50
 13  \w     37.00  62.00   0.50    0.50    --   42.30 -77.00 150.00   50
 14  \w     15.00  55.00   0.50    0.50    --   42.30  54.00 150.00   80
 15  \w     77.00 126.00   0.50    0.50    --   42.30  77.00  60.00   98
 16  \w     88.00 119.00   0.50    0.50    --   42.30  65.00-180.00   62
 17  \w     28.00  53.00   0.50    0.50    --   42.30  65.00  90.00   50
 18  \w      8.00  94.00   0.50    0.50    --   93.70 -82.00-120.00  172
 19  \w     98.00 126.00   0.50    0.50    --   93.70  33.00  90.00   56
 20  \w     60.00  85.00   0.50    0.50    --   93.70  33.00  90.00   50
 21  \w     97.00 123.00   0.50    0.50    --   93.70 -42.00  30.00   52
 22  \w     20.00  70.00   0.50    0.50    --   93.70 -42.00  30.00  100
 23  \w      4.00 107.00   0.50    0.50    --   93.70 -82.00-180.00  206
 24  \w      4.00  78.00   0.50    0.50    --   93.70   0.00  30.00  148
 25  \w     38.00  80.00   0.50    0.50    --   93.70 -82.00 -60.00   84
 26  \w     49.00  94.00   0.50    0.50    --   93.70 -82.00 120.00   90
 27  \w      5.00  30.00   0.50    0.50    --   93.70 -82.00 120.00   50
 28  \w     39.00  65.00   0.50    0.50    --   93.70 -82.00-150.00   52
 29  \w    158.00 183.00   0.50    0.50    --   93.70  33.00  90.00   50
 30  \w     16.00  67.00   0.50    0.50    --   93.70 -68.00 120.00  102
 31  \w     77.00 119.00   0.50    0.50    --   93.70 -33.00 120.00   84
 32  \w     14.00 128.00   0.50    0.50    --   93.70 -33.00-120.00  228
 33  \w     69.00 138.00   0.50    0.50    --   93.70  68.00 120.00  138
 34  \w     21.00  88.00   0.50    0.50    --   93.70 -82.00  30.00  134
 35  \w     14.00 102.00   0.50    0.50    --   93.70 -82.00 -90.00  176
 36  \w     36.00  92.00   0.50    0.50    --   93.70 -82.00   0.00  112
 37  \w    108.00 183.00   0.50    0.50    --   93.70  50.00 -30.00  150
 38  \w    129.00 183.00   0.50    0.50    --   93.70   0.00  30.00  108
 39  \w     43.00 103.00   0.50    0.50    --   93.70 -82.00  61.02  120
 40  \w     96.00 121.00   0.50    0.50    --   93.70 -82.00-150.00   50
 41  \w     39.00  97.00   0.50    0.50    --   93.70 -82.00 -30.00  116
 42  \w     63.00  88.00   0.50    0.50    --   93.70 -82.00 150.00   50
 43  \w      5.00  30.00   0.50    0.50    --   93.70 -82.00  61.02   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1258540000
_diffrn_orient_matrix_UB_12      0.0334544000
_diffrn_orient_matrix_UB_13      -0.0004606000
_diffrn_orient_matrix_UB_21      -0.0428297000
_diffrn_orient_matrix_UB_22      -0.0772941000
_diffrn_orient_matrix_UB_23      0.0777284000
_diffrn_orient_matrix_UB_31      0.0258206000
_diffrn_orient_matrix_UB_32      0.0348505000
_diffrn_orient_matrix_UB_33      0.1731097000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13654
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.207
_diffrn_reflns_theta_min         3.887
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.929
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0106(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0494P)^2^+0.3172P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0945
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2651
_reflns_number_total             2849
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00001j2.cif
_cod_data_source_block           w2_auto
_cod_depositor_comments          'Adding full bibliography for 7159214.cif.'
_cod_database_code               7159214
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.927
_shelx_estimated_absorpt_t_min   0.893
_diffrn_oxdiff_digest_frames
;
019d4754dbfeaa8797972333194f1ae0e000030b280
;
_diffrn_oxdiff_digest_hkl
;
01388333e4a277d56880de7f908acbb2169853
;
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20)
;
_shelx_res_checksum              65344
_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 1.481
_oxdiff_exptl_absorpt_empirical_full_min 0.685