Efficient synthesis of cyclic amidine-based fluorophores via 6π-electrocyclic ring closure
Li, Guofeng; Zhao, Man; Xie, Junqiu; Yao, Ying; Mou, Lingyun; Zhang, Xiaowei; Guo, Xiaomin; Sun, Wangsheng; Wang, Zheng; Xu, Jiecheng; Xue, Jianzhong; Hu, Tao; Zhang, Ming; Li, Min; Hong, Liang; Chemical Science 11 (2020) 3586–3591; doi:10.1039/D0SC00798F

data_1557603
_publ_section_title
;
 Efficient synthesis of cyclic amidine-based fluorophores via
 6\p-electrocyclic ring closure
;
_journal_issue                   14
_journal_name_full               'Chemical Science'
_journal_page_first              3586
_journal_page_last               3591
_journal_paper_doi               10.1039/D0SC00798F
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C21 H17 N3 O2 S'
_chemical_formula_sum            'C21 H18 N2 O2 S'
_chemical_formula_weight         362.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-22 deposited with the CCDC.	2020-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.5756(17)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.4822(3)
_cell_length_b                   9.78677(16)
_cell_length_c                   20.9912(4)
_cell_measurement_reflns_used    4653
_cell_measurement_temperature    100
_cell_measurement_theta_max      75.3260
_cell_measurement_theta_min      2.1450
_cell_volume                     3491.13(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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    -22.00  69.00   1.00    1.00    --   44.06 -57.00 -90.00   91
  2  \w     33.00 121.00   1.00    2.00    --  107.00-125.00-120.00   88
  3  \w    105.00 131.00   1.00    2.00    --  107.00 -45.00-120.00   26
  4  \w     50.00  92.00   1.00    1.00    --   44.06  57.00-150.00   42
  5  \w     73.00 113.00   1.00    1.00    --   44.06 125.00 -60.00   40
  6  \w     45.00 129.00   1.00    2.00    --  107.00 -45.00   0.00   84
  7  \w     82.00 178.00   1.00    2.00    --  107.00  30.00  60.00   96
  8  \w     89.00 115.00   1.00    1.00    --   44.06 125.00 150.00   26
  9  \w     36.00  64.00   1.00    2.00    --  107.00 -45.00-120.00   28
 10  \w     38.00  96.00   1.00    2.00    --  107.00 -94.00 -30.00   58
 11  \w     73.00  98.00   1.00    1.00    --   44.06 125.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0221500000
_diffrn_orient_matrix_UB_12      0.0617846000
_diffrn_orient_matrix_UB_13      0.0607587000
_diffrn_orient_matrix_UB_21      -0.0300797000
_diffrn_orient_matrix_UB_22      -0.1405983000
_diffrn_orient_matrix_UB_23      0.0163835000
_diffrn_orient_matrix_UB_31      0.0826009000
_diffrn_orient_matrix_UB_32      -0.0347135000
_diffrn_orient_matrix_UB_33      0.0416716000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6290
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         4.334
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.793
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3089
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0518P)^2^+2.4122P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2793
_reflns_number_total             3089
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc00798f2.cif
_cod_data_source_block           lgf_180809
_cod_depositor_comments
;Adding full bibliography for 1557603.cif.

 Adding full bibliography for 1557603.cif.
;
_cod_original_cell_volume        3491.14(11)
_cod_database_code               1557603
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.841
_shelx_estimated_absorpt_t_min   0.615
_reflns_odcompleteness_completeness 99.22
_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:
 C6(H6), C8(H8), C10(H10), C11(H11), C12(H12), C14(H14), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_shelx_res_checksum              99946
_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 2.608
_oxdiff_exptl_absorpt_empirical_full_min 0.484