Systematic color tuning of a family of luminescent azole-based organoboron compounds suitable for OLED applications.
Kiprof, Paul; Carlson, Jeffrey C.; Anderson, Derrick R.; Nemykin, Victor N.; Dalton transactions (Cambridge, England : 2003) 42 (2013) 15120–15132; doi:10.1039/c3dt51853a

data_7023730
_publ_section_title
;
 Systematic color tuning of a family of luminescent azole-based
 organoboron compounds suitable for OLED applications.
;
_journal_issue                   42
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              15120
_journal_page_last               15132
_journal_paper_doi               10.1039/c3dt51853a
_journal_volume                  42
_journal_year                    2013
_chemical_formula_moiety         'C25 H18 B1 N1 O1 S1'
_chemical_formula_sum            'C25 H18 B N O S'
_chemical_formula_weight         391.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             11-09-15
_audit_creation_method           CRYSTALS_ver_14.11
_cell_angle_alpha                90
_cell_angle_beta                 101.51(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.767(2)
_cell_length_b                   13.621(3)
_cell_length_c                   15.317(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      18
_cell_measurement_theta_min      15
_cell_volume                     1996.7(7)
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Rigaku AFC-7R'
_diffrn_measurement_device_type  Four-circle
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4788
_diffrn_reflns_theta_full        27.504
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_min         2.019
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.49
_refine_diff_density_min         -0.41
_refine_ls_extinction_coef       97(18)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9973
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4569
_refine_ls_number_restraints     126
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0.0017875
_refine_ls_shift/su_mean         0.0001002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 29.7 46.2 22.1 5.31 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1904
_refine_ls_wR_factor_gt          0.1478
_refine_ls_wR_factor_ref         0.1904
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                3237
_reflns_number_total             4585
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.93
_oxford_diffrn_Wilson_scale      6.64
_oxford_refine_ls_r_factor_ref   0.0823
_oxford_refine_ls_scale          0.4163(11)
_oxford_reflns_number_all        4569
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'P21n in P2(1)/n'
_cod_data_source_file            c3dt51853a.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_original_formula_sum        'C25 H18 B1 N1 O1 S1'
_cod_database_code               7023730
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT S    (    1 ,X'S,U'S)  UNTIL C    (   12 ) 
CONT H    (   14 ,X'S)  UNTIL H    (   10 ) 
CONT EXTPARAM 
END                                                                             
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_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 18) TO H(14) 
REST 0.083, 0.002 = H(14,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(14) TO C ( 18) TO C(19) 
CONT H(14) TO C ( 18) TO C(17) 
PLANAR C ( 18) C(19) C(17) H(14) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 17) TO H(13) 
REST 0.089, 0.002 = H(13,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(13) TO C ( 17) TO C(18) 
CONT H(13) TO C ( 17) TO C(16) 
PLANAR C ( 17) C(18) C(16) H(13) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 16) TO H(12) 
REST 0.086, 0.002 = H(12,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(12) TO C ( 16) TO C(17) 
CONT H(12) TO C ( 16) TO C(15) 
PLANAR C ( 16) C(17) C(15) H(12) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 15) TO H(11) 
REST 0.072, 0.002 = H(11,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(11) TO C ( 15) TO C(14) 
CONT H(11) TO C ( 15) TO C(16) 
PLANAR C ( 15) C(14) C(16) H(11) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 25) TO H(18) 
REST 0.068, 0.002 = H(18,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(18) TO C ( 25) TO C(20) 
CONT H(18) TO C ( 25) TO C(24) 
PLANAR C ( 25) C(20) C(24) H(18) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 24) TO H(17) 
REST 0.080, 0.002 = H(17,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(17) TO C ( 24) TO C(25) 
CONT H(17) TO C ( 24) TO C(23) 
PLANAR C ( 24) C(25) C(23) H(17) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 23) TO H(16) 
REST 0.075, 0.002 = H(16,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(16) TO C ( 23) TO C(24) 
CONT H(16) TO C ( 23) TO C(22) 
PLANAR C ( 23) C(24) C(22) H(16) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 22) TO H(15) 
REST 0.066, 0.002 = H(15,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(15) TO C ( 22) TO C(21) 
CONT H(15) TO C ( 22) TO C(23) 
PLANAR C ( 22) C(21) C(23) H(15) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 2) TO H(1) 
REST 0.070, 0.002 = H(1,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(1) TO C ( 2) TO C(1) 
CONT H(1) TO C ( 2) TO C(3) 
PLANAR C ( 2) C(1) C(3) H(1) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 3) TO H(2) 
REST 0.090, 0.002 = H(2,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(2) TO C ( 3) TO C(2) 
CONT H(2) TO C ( 3) TO C(4) 
PLANAR C ( 3) C(2) C(4) H(2) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 4) TO H(3) 
REST 0.090, 0.002 = H(3,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(3) TO C ( 4) TO C(3) 
CONT H(3) TO C ( 4) TO C(5) 
PLANAR C ( 4) C(3) C(5) H(3) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 5) TO H(4) 
REST 0.089, 0.002 = H(4,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(4) TO C ( 5) TO C(4) 
CONT H(4) TO C ( 5) TO C(6) 
PLANAR C ( 5) C(4) C(6) H(4) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 6) TO H(5) 
REST 0.072, 0.002 = H(5,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(5) TO C ( 6) TO C(1) 
CONT H(5) TO C ( 6) TO C(5) 
PLANAR C ( 6) C(1) C(5) H(5) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 8) TO H(6) 
REST 0.061, 0.002 = H(6,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(6) TO C ( 8) TO C(7) 
CONT H(6) TO C ( 8) TO C(9) 
PLANAR C ( 8) C(7) C(9) H(6) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 9) TO H(7) 
REST 0.076, 0.002 = H(7,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(7) TO C ( 9) TO C(8) 
CONT H(7) TO C ( 9) TO C(10) 
PLANAR C ( 9) C(8) C(10) H(7) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 10) TO H(8) 
REST 0.082, 0.002 = H(8,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(8) TO C ( 10) TO C(9) 
CONT H(8) TO C ( 10) TO C(11) 
PLANAR C ( 10) C(9) C(11) H(8) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 11) TO H(9) 
REST 0.088, 0.002 = H(9,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(9) TO C ( 11) TO C(10) 
CONT H(9) TO C ( 11) TO C(12) 
PLANAR C ( 11) C(10) C(12) H(9) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 12) TO H(10) 
REST 0.070, 0.002 = H(10,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(10) TO C ( 12) TO C(7) 
CONT H(10) TO C ( 12) TO C(11) 
PLANAR C ( 12) C(7) C(11) H(10) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;