3-Thiolated pyrroles/pyrrolines: controllable synthesis and usage for the construction of thiolated fluorophores.
Tian, Jun; Yuan, Kang-Ning; Liu, Wen; Chang, Hong-Hong; Li, Xing; Gao, Wen-Chao; Chemical communications (Cambridge, England) 57 (2021) 1943–1946; doi:10.1039/d0cc07988j

data_7127832
_publ_section_title
;
 3-Thiolated pyrroles/pyrrolines: controllable synthesis and usage for the
 construction of thiolated fluorophores.
;
_journal_issue                   15
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1943
_journal_page_last               1946
_journal_paper_doi               10.1039/d0cc07988j
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H22 Cl N O2 S2'
_chemical_formula_sum            'C29 H22 Cl N O2 S2'
_chemical_formula_weight         516.05
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-09-18
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2020-10-10 deposited with the CCDC.	2021-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.414(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.0048(3)
_cell_length_b                   11.7155(5)
_cell_length_c                   13.6559(5)
_cell_measurement_reflns_used    2783
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9780
_cell_measurement_theta_min      6.3100
_cell_volume                     1279.52(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9979
_diffrn_measured_fraction_theta_max 0.7350
_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    -11.00  20.00   1.00    1.00    --    0.00 -57.00 -30.00   31
  2  \w      0.00  25.00   1.00    1.00    --    0.00  57.00  90.00   25
  3  \w    -67.00 -27.00   1.00    1.00    --    0.00 -57.00 -30.00   40
  4  \w     72.00 120.00   1.00    1.00    --   54.00  57.00 -30.00   48
  5  \w     72.00 120.00   1.00    1.00    --   54.00  57.00   0.00   48
  6  \w     34.00  68.00   1.00    1.00    --   54.00  57.00 -30.00   34
  7  \w     73.00 116.00   1.00    1.00    --   54.00  57.00-120.00   43
  8  \w     24.00 108.00   1.00    1.00    --   54.00-125.00-180.00   84
  9  \w     29.00  55.00   1.00    1.00    --   54.00-125.00 -60.00   26
 10  \w     48.00  94.00   1.00    1.00    --  108.00-111.00 -60.00   46
 11  \w     80.00 173.00   1.00    1.00    --  108.00  25.00 120.00   93
 12  \w    117.00 146.00   1.00    1.00    --  108.00 111.00 -90.00   29
 13  \w     75.00 100.00   1.00    1.00    --  108.00  25.00-150.00   25
 14  \w    108.00 133.00   1.00    1.00    --  108.00  25.00-150.00   25
 15  \w    101.00 136.00   1.00    1.00    --  108.00 111.00   0.00   35
 16  \w     37.00  68.00   1.00    1.00    --  108.00-111.00 -90.00   31
 17  \w     50.00 112.00   1.00    1.00    --  108.00-111.00-180.00   62
 18  \w    123.00 166.00   1.00    1.00    --  108.00 111.00  90.00   43
 19  \w    153.00 178.00   1.00    1.00    --  108.00  25.00-150.00   25
 20  \w     62.00 130.00   1.00    1.00    --  108.00 -63.00 -60.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1546861000
_diffrn_orient_matrix_UB_12      -0.0508952000
_diffrn_orient_matrix_UB_13      0.0473267000
_diffrn_orient_matrix_UB_21      0.0315005000
_diffrn_orient_matrix_UB_22      -0.1149723000
_diffrn_orient_matrix_UB_23      -0.0506642000
_diffrn_orient_matrix_UB_31      0.1107132000
_diffrn_orient_matrix_UB_32      -0.0385258000
_diffrn_orient_matrix_UB_33      0.0889811000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4814
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         3.24
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.061
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(13)
_refine_ls_extinction_coef       0.0025(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         3484
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+0.0797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0896
_reflns_number_gt                3365
_reflns_number_total             3484
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0cc07988j2.cif
_cod_data_source_block           exp_3880
_cod_depositor_comments
'Adding full bibliography for 7127832--7127833.cif.'
_cod_database_code               7127832
_chemical_oxdiff_formula         'C1 H1 N1 O1 S1'
_chemical_oxdiff_usercomment     CHOS
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C18(H18), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25),
  C27(H27), C28(H28)
2.b Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.880
_oxdiff_exptl_absorpt_empirical_full_min 0.584