Achieving high-efficiency purely organic room-temperature phosphorescence from boronic ester substitution of phenoxathiine
Li, Mengke; Cai, Xinyi; Qiao, Zhenyang; Liu, Kunkun; Xie, Wentao; Wang, Liangying; Zheng, Nan; Su, Shi-Jian; Chemical Communications  (2019) –; doi:10.1039/C9CC02648G

data_7123532
_publ_section_title
;
 Achieving high-efficiency purely organic room-temperature phosphorescence
 from boronic ester substitution of phenoxathiine
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC02648G
_journal_year                    2019
_chemical_formula_moiety         'C18 H19 B O2 S2'
_chemical_formula_sum            'C18 H19 B O2 S2'
_chemical_formula_weight         342.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-08 deposited with the CCDC.    2019-05-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.511(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.46310(10)
_cell_length_b                   10.9896(2)
_cell_length_c                   11.8559(3)
_cell_measurement_reflns_used    12266
_cell_measurement_temperature    100.0(9)
_cell_measurement_theta_max      73.0230
_cell_measurement_theta_min      4.0370
_cell_volume                     842.05(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(9)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_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    -70.00  11.00   0.50    0.50    --    0.00 -19.00 150.00  162
  2  \w    -76.00 -35.00   0.50    0.50    --    5.00 -19.00 -90.00   82
  3  \w    -59.00 -33.00   0.50    0.50    --  -98.80  57.00-180.00   52
  4  \w   -112.00 -63.00   0.50    0.50    --  -98.80  57.00-180.00   98
  5  \w   -108.00 -38.00   0.50    0.50    --  -98.80  72.00 -30.00  140
  6  \w   -184.00-157.00   0.50    0.50    --  -98.80 -38.00 120.00   54
  7  \w   -174.00-102.00   0.50    0.50    --  -98.80 -19.00 -60.00  144
  8  \w   -185.00 -99.00   0.50    0.50    --  -98.80 -57.00-120.00  172
  9  \w    -36.00   7.00   0.50    0.50    --    0.00 -57.00-180.00   86
 10  \w   -117.00 -92.00   0.50    0.50    --  -34.00 -66.00 156.76   50
 11  \w    -46.00 -21.00   0.50    0.50    --  -34.00 -67.00 -92.29   50
 12  \w    -68.00 -23.00   0.50    0.50    --  -34.00 -66.00 156.76   90
 13  \w   -121.00 -96.00   0.50    0.50    --  -38.00 -66.00 124.02   50
 14  \w    -53.00 -27.00   0.50    0.50    --  -38.00 -66.00 124.02   52
 15  \w    -51.00 -25.00   0.50    0.50    --  -38.00 -67.00  29.86   52
 16  \w   -123.00 -96.00   0.50    0.50    --  -38.00 -67.00  29.86   54
 17  \w    -52.00 -25.00   0.50    0.50    --  -38.00 -71.00 172.32   54
 18  \w    -57.00 -31.00   0.50    0.50    --  -42.00 -71.00 -28.59   52
 19  \w    -54.00 -29.00   0.50    0.50    --  -42.00 -66.00  -5.87   50
 20  \w    -61.00 -33.00   0.50    0.50    --  -46.00 -67.00  95.34   56
 21  \w    -59.00 -33.00   0.50    0.50    --  -46.00 -67.00-160.25   52
 22  \w    -60.00 -34.00   0.50    0.50    --  -46.00 -53.00  30.49   52
 23  \w    -62.00 -37.00   0.50    0.50    --  -50.00 -68.00-108.96   50
 24  \w    -63.00 -38.00   0.50    0.50    --  -50.00 -60.00-149.57   50
 25  \w    -62.00 -37.00   0.50    0.50    --  -50.00 -69.00 141.07   50
 26  \w    -63.00 -37.00   0.50    0.50    --  -50.00 -69.00 -35.78   52
 27  \w    -73.00 -47.00   0.50    0.50    --  -58.00 -60.00-172.37   52
 28  \w    -77.00 -45.00   0.50    0.50    --  -58.00 -70.00  95.24   64
 29  \w    -71.00 -45.00   0.50    0.50    --  -58.00 -71.00  17.20   52
 30  \w    -73.00 -48.00   0.50    0.50    --  -58.00 -59.00  35.87   50
 31  \w    -73.00 -47.00   0.50    0.50    --  -58.00 -63.00 -59.00   52
 32  \w   -141.00-115.00   0.50    0.50    --  -62.00 -63.00 119.41   52
 33  \w    -74.00 -49.00   0.50    0.50    --  -62.00 -63.00 119.41   50
 34  \w    -75.00 -49.00   0.50    0.50    --  -62.00 -69.00-162.62   52
 35  \w    -75.00 -49.00   0.50    0.50    --  -62.00 -68.00 -66.39   52
 36  \w   -150.00-113.00   0.50    0.50    --  -62.00 -69.00-162.62   74
 37  \w    -81.00 -55.00   0.50    0.50    --  -66.00 -69.00 -15.87   52
 38  \w    -78.00 -53.00   0.50    0.50    --  -66.00 -63.00 151.65   50
 39  \w    -87.00 -55.00   0.50    0.50    --  -66.00 -61.00 -94.62   64
 40  \w    -85.00 -59.00   0.50    0.50    --  -70.00 -61.00 106.23   52
 41  \w   -158.00-132.00   0.50    0.50    --  -70.00 -61.00 106.23   52
 42  \w    -82.00 -57.00   0.50    0.50    --  -70.00 -67.00-105.47   50
 43  \w   -159.00-127.00   0.50    0.50    --  -70.00 -67.00-105.47   64
 44  \w    -89.00 -63.00   0.50    0.50    --  -70.00 -52.00  43.99   52
 45  \w   -159.00-132.00   0.50    0.50    --  -70.00 -67.00  12.92   54
 46  \w    -84.00 -58.00   0.50    0.50    --  -70.00 -67.00  12.92   52
 47  \w    -88.00 -57.00   0.50    0.50    --  -70.00 -68.00  42.15   62
 48  \w    -83.00 -57.00   0.50    0.50    --  -70.00 -65.00  -1.77   52
 49  \w    -86.00 -61.00   0.50    0.50    --  -74.00 -61.00  51.49   50
 50  \w   -149.00-124.00   0.50    0.50    --  -74.00 -63.00-129.80   50
 51  \w    -88.00 -61.00   0.50    0.50    --  -74.00 -63.00-129.80   54
 52  \w    -89.00 -63.00   0.50    0.50    --  -74.00 -62.00-147.43   52
 53  \w    -88.00 -62.00   0.50    0.50    --  -74.00 -61.00  87.44   52
 54  \w    -72.00 -28.00   0.50    0.50    --  -74.00  66.00 105.80   88
 55  \w    -94.00 -61.00   0.50    0.50    --  -74.00 -61.00 138.38   66
 56  \w   -108.00 -66.00   0.50    0.50    --  -78.00 -63.00 -59.41   84
 57  \w    -97.00 -71.00   0.50    0.50    --  -82.00 -58.00  41.09   52
 58  \w   -102.00 -70.00   0.50    0.50    --  -82.00 -61.00 -71.24   64
 59  \w    -95.00 -69.00   0.50    0.50    --  -82.00 -70.00 -96.09   52
 60  \w   -163.00-137.00   0.50    0.50    --  -86.00 -43.00 -95.80   52
 61  \w   -119.00 -93.00   0.50    0.50    --  -86.00 -43.00 -95.80   52
 62  \w   -108.00 -75.00   0.50    0.50    --  -86.00 -62.00 -24.43   66
 63  \w   -175.00-149.00   0.50    0.50    --  -86.00 -62.00 -24.43   52
 64  \w   -100.00 -74.00   0.50    0.50    --  -86.00 -54.00  20.89   52
 65  \w   -155.00 -75.00   0.50    0.50    --  -86.00 -55.00 127.22  160
 66  \w    -99.00 -73.00   0.50    0.50    --  -86.00 -60.00 164.13   52
 67  \w    -98.00 -73.00   0.50    0.50    --  -86.00 -60.00-153.46   50
 68  \w   -174.00-129.00   0.50    0.50    --  -86.00 -60.00-153.46   90
 69  \w   -101.00 -73.00   0.50    0.50    --  -86.00 -53.00 176.56   56
 70  \w    -98.00 -73.00   0.50    0.50    --  -86.00 -59.00 -14.46   50
 71  \w    -98.00 -73.00   0.50    0.50    --  -86.00 -60.00 -87.05   50
 72  \w   -130.00-104.00   0.50    0.50    --  -86.00 -60.00 -87.05   52
 73  \w   -142.00 -77.00   0.50    0.50    --  -90.00 -61.00   5.84  130
 74  \w   -178.00-146.00   0.50    0.50    --  -90.00 -61.00   5.84   64
 75  \w    -59.00 -24.00   0.50    0.50    --  -90.00  72.00 -88.68   70
 76  \w   -104.00 -66.00   0.50    0.50    --  -90.00  72.00 -88.68   76
 77  \w   -133.00 -77.00   0.50    0.50    --  -90.00 -71.00-161.21  112
 78  \w   -166.00-140.00   0.50    0.50    --  -90.00 -71.00-161.21   52
 79  \w   -112.00 -77.00   0.50    0.50    --  -90.00 -70.00  77.05   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2224527000
_diffrn_orient_matrix_UB_12      0.0378133000
_diffrn_orient_matrix_UB_13      0.0293841000
_diffrn_orient_matrix_UB_21      -0.0161280000
_diffrn_orient_matrix_UB_22      0.0717279000
_diffrn_orient_matrix_UB_23      -0.1113131000
_diffrn_orient_matrix_UB_31      -0.0841933000
_diffrn_orient_matrix_UB_32      -0.1144087000
_diffrn_orient_matrix_UB_33      -0.0601475000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13579
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.023
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    2.902
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72026
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
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    1.350
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.254
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 1345 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.031(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2882
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0455
_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^)+(0.0701P)^2^+1.2060P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1275
_reflns_Friedel_coverage         0.921
_reflns_Friedel_fraction_full    0.926
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                2866
_reflns_number_total             2882
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc02648g2.cif
_cod_data_source_block           ptt-b
_cod_database_code               7123532
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.56
_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:
 C006(H006), C009(H009), C00A(H00A), C00C(H00C), C00D(H00D), C00E(H00E),
 C00F(H00F)
2.b Idealised Me refined as rotating group:
 C00J(H00B,H00G,H00H), C00K(H00I,H00J,H00K), C00M(H00L,H00M,H00N), C00N(H00O,
 H00P,H00Q)
;
_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 1.493
_oxdiff_exptl_absorpt_empirical_full_min 0.589