#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/68/7236863.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7236863
loop_
_publ_author_name
'He, Zuozheng'
'Cai, Xinyi'
'Wang, Zhiheng'
'Li, Yunchuan'
'Xu, Zhida'
'Liu, Kunkun'
'Chen, Dongcheng'
'Su, Shi-Jian'
_publ_section_title
;
 Sky-blue thermally activated delayed fluorescence material employing a
 diphenylethyne acceptor for organic light-emitting diodes
;
_journal_issue                   1
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              36
_journal_paper_doi               10.1039/C7TC02763J
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         'C44 H36 N2'
_chemical_formula_sum            'C44 H36 N2'
_chemical_formula_weight         592.75
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-06-14 deposited with the CCDC.
2017-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.337(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.3224(7)
_cell_length_b                   21.5654(17)
_cell_length_c                   8.0810(5)
_cell_measurement_reflns_used    3969
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      72.4610
_cell_measurement_theta_min      4.0680
_cell_volume                     1598.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.11a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.11a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.11a (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  27.00   0.50    0.50    --    5.00  38.00  60.00   72
  2  ω     53.00  94.00   0.50    0.50    --    5.00  38.00  60.00   82
  3  ω    -59.00  -9.00   0.50    0.50    --  -45.20  72.00   0.00  100
  4  ω    -76.00 -46.00   0.50    0.50    -- -100.10  72.00   0.00   60
  5  ω    -91.00 -11.00   0.50    0.50    -- -100.10  57.00  90.00  160
  6  ω    -93.00 -68.00   0.50    0.50    -- -100.10  72.00 120.00   50
  7  ω   -110.00 -81.00   0.50    0.50    -- -100.10  72.00   0.00   58
  8  ω   -105.00 -11.00   0.50    0.50    -- -100.10  72.00  30.00  188
  9  ω   -105.00 -79.00   0.50    0.50    -- -100.10  72.00  60.00   52
 10  ω    -97.00 -11.00   0.50    0.50    -- -100.10  72.00  90.00  172
 11  ω   -115.00 -65.00   0.50    0.50    --  -45.20 -38.00  60.00  100
 12  ω    -69.00 -38.00   0.50    0.50    --  -45.20 -72.00 -30.00   62
 13  ω   -112.00 -11.00   0.50    0.50    -- -100.10  19.00 -90.00  202
 14  ω   -114.00 -65.00   0.50    0.50    -- -100.10  57.00   0.00   98
 15  ω   -109.00 -13.00   0.50    0.50    -- -100.10  19.00  30.00  192
 16  ω   -121.00 -90.00   0.50    0.50    -- -100.10 -57.00-120.00   62
 17  ω   -135.00 -88.00   0.50    0.50    --  -45.20 -72.00 -30.00   94
 18  ω   -172.00-133.00   0.50    0.50    -- -100.10 -57.00-120.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0454785000
_diffrn_orient_matrix_UB_12      -0.0680388000
_diffrn_orient_matrix_UB_13      0.0312097000
_diffrn_orient_matrix_UB_21      0.1613457000
_diffrn_orient_matrix_UB_22      0.0202214000
_diffrn_orient_matrix_UB_23      0.0390820000
_diffrn_orient_matrix_UB_31      -0.0098879000
_diffrn_orient_matrix_UB_32      0.0071692000
_diffrn_orient_matrix_UB_33      0.1872434000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            8858
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         4.100
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.541
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.11a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      ?
_exptl_crystal_description       stick
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2813
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0430
_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/[σ²(Fo²)+(0.0513P)²+0.4962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1152
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2460
_reflns_number_total             2813
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7tc02763j2.cif
_cod_data_source_block           y-3-2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               7236863
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 98.51
_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:
 C003(H003), C007(H007), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E),
 C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L)
2.b Idealised Me refined as rotating group:
 C00M(H00A,H00G,H00M), C00N(H00N,H00O,H00P)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.342
_oxdiff_exptl_absorpt_empirical_full_min 0.486
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
N001 N 0.64541(13) 0.39601(6) 0.52742(14) 0.0322(3) Uani 1 1 d .
C002 C 0.72556(15) 0.42138(7) 0.40608(17) 0.0313(3) Uani 1 1 d .
C003 C 0.75797(16) 0.38408(7) 0.27812(18) 0.0334(3) Uani 1 1 d .
H003 H 0.7266 0.3431 0.2698 0.040 Uiso 1 1 calc R
C004 C 0.72484(16) 0.35837(7) 0.65584(17) 0.0307(3) Uani 1 1 d .
C005 C 0.88512(15) 0.46903(7) 0.17496(18) 0.0337(3) Uani 1 1 d .
C006 C 0.49494(16) 0.38429(7) 0.47463(18) 0.0330(3) Uani 1 1 d .
C007 C 0.83668(16) 0.40758(7) 0.16280(18) 0.0355(4) Uani 1 1 d .
H007 H 0.8575 0.3824 0.0767 0.043 Uiso 1 1 calc R
C008 C 0.64984(17) 0.32746(7) 0.76799(18) 0.0336(3) Uani 1 1 d .
C009 C 0.41691(17) 0.35464(7) 0.58536(19) 0.0368(4) Uani 1 1 d .
C00A C 0.96661(16) 0.49195(7) 0.05340(19) 0.0373(4) Uani 1 1 d .
C00B C 0.42232(17) 0.40209(8) 0.31469(18) 0.0381(4) Uani 1 1 d .
H00B H 0.4723 0.4238 0.2433 0.046 Uiso 1 1 calc R
C00C C 0.87518(17) 0.35156(8) 0.67273(18) 0.0370(4) Uani 1 1 d .
H00C H 0.9258 0.3739 0.6032 0.044 Uiso 1 1 calc R
C00D C 0.85284(17) 0.50577(7) 0.3052(2) 0.0391(4) Uani 1 1 d .
H00D H 0.8853 0.5466 0.3151 0.047 Uiso 1 1 calc R
C00E C 0.77316(17) 0.48247(7) 0.42026(19) 0.0371(4) Uani 1 1 d .
H00E H 0.7517 0.5075 0.5063 0.044 Uiso 1 1 calc R
C00F C 0.72701(19) 0.28618(7) 0.88229(19) 0.0404(4) Uani 1 1 d .
H00F H 0.6775 0.2636 0.9525 0.048 Uiso 1 1 calc R
C00G C 0.49249(17) 0.34586(8) 0.76786(19) 0.0417(4) Uani 1 1 d .
C00H C 0.95005(19) 0.31156(8) 0.7930(2) 0.0443(4) Uani 1 1 d .
H00H H 1.0507 0.3078 0.8047 0.053 Uiso 1 1 calc R
C00I C 0.27159(17) 0.33949(8) 0.5268(2) 0.0444(4) Uani 1 1 d .
H00I H 0.2202 0.3182 0.5974 0.053 Uiso 1 1 calc R
C00J C 0.27657(18) 0.38764(9) 0.2621(2) 0.0456(4) Uani 1 1 d .
H00J H 0.2292 0.3998 0.1559 0.055 Uiso 1 1 calc R
C00K C 0.87610(19) 0.27759(8) 0.8948(2) 0.0441(4) Uani 1 1 d .
H00K H 0.9254 0.2492 0.9711 0.053 Uiso 1 1 calc R
C00L C 0.20122(18) 0.35525(9) 0.3665(2) 0.0481(4) Uani 1 1 d .
H00L H 0.1044 0.3442 0.3297 0.058 Uiso 1 1 calc R
C00M C 0.4938(2) 0.40983(10) 0.8552(2) 0.0520(5) Uani 1 1 d .
H00A H 0.5451 0.4066 0.9690 0.078 Uiso 1 1 calc GR
H00G H 0.3954 0.4230 0.8552 0.078 Uiso 1 1 calc GR
H00M H 0.5417 0.4396 0.7956 0.078 Uiso 1 1 calc GR
C00N C 0.4137(2) 0.29915(12) 0.8626(2) 0.0685(6) Uani 1 1 d .
H00N H 0.4096 0.2597 0.8072 0.103 Uiso 1 1 calc GR
H00O H 0.3165 0.3135 0.8642 0.103 Uiso 1 1 calc GR
H00P H 0.4657 0.2950 0.9759 0.103 Uiso 1 1 calc GR
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
C004 N001 C002 116.65(11) .
C006 N001 C002 118.00(11) .
C006 N001 C004 118.57(12) .
C003 C002 N001 119.73(13) .
C003 C002 C00E 120.21(13) .
C00E C002 N001 120.04(13) .
C002 C003 H003 119.9 .
C007 C003 C002 120.25(14) .
C007 C003 H003 119.9 .
C008 C004 N001 119.21(13) .
C00C C004 N001 121.14(13) .
C00C C004 C008 119.65(13) .
C007 C005 C00A 118.88(14) .
C00D C005 C007 118.78(13) .
C00D C005 C00A 122.34(14) .
C009 C006 N001 119.24(13) .
C00B C006 N001 121.23(13) .
C00B C006 C009 119.53(14) .
C003 C007 C005 120.28(14) .
C003 C007 H007 119.9 .
C005 C007 H007 119.9 .
C004 C008 C00G 117.83(13) .
C00F C008 C004 118.32(14) .
C00F C008 C00G 123.59(14) .
C006 C009 C00G 118.00(13) .
C00I C009 C006 118.31(14) .
C00I C009 C00G 123.47(14) .
C00A C00A C005 176.3(2) 3_765
C006 C00B H00B 119.8 .
C00J C00B C006 120.44(14) .
C00J C00B H00B 119.8 .
C004 C00C H00C 119.8 .
C00H C00C C004 120.31(14) .
C00H C00C H00C 119.8 .
C005 C00D H00D 119.5 .
C00E C00D C005 121.05(14) .
C00E C00D H00D 119.5 .
C002 C00E H00E 120.3 .
C00D C00E C002 119.42(14) .
C00D C00E H00E 120.3 .
C008 C00F H00F 119.1 .
C008 C00F C00K 121.81(15) .
C00K C00F H00F 119.1 .
C008 C00G C009 108.12(12) .
C008 C00G C00M 107.68(13) .
C008 C00G C00N 112.19(15) .
C009 C00G C00M 107.11(13) .
C009 C00G C00N 112.64(14) .
C00N C00G C00M 108.87(15) .
C00C C00H H00H 119.8 .
C00K C00H C00C 120.39(16) .
C00K C00H H00H 119.8 .
C009 C00I H00I 119.0 .
C00L C00I C009 121.96(15) .
C00L C00I H00I 119.0 .
C00B C00J H00J 119.8 .
C00L C00J C00B 120.36(15) .
C00L C00J H00J 119.8 .
C00F C00K H00K 120.4 .
C00H C00K C00F 119.22(15) .
C00H C00K H00K 120.4 .
C00I C00L H00L 120.4 .
C00J C00L C00I 119.22(15) .
C00J C00L H00L 120.4 .
C00G C00M H00A 109.5 .
C00G C00M H00G 109.5 .
C00G C00M H00M 109.5 .
H00A C00M H00G 109.5 .
H00A C00M H00M 109.5 .
H00G C00M H00M 109.5 .
C00G C00N H00N 109.5 .
C00G C00N H00O 109.5 .
C00G C00N H00P 109.5 .
H00N C00N H00O 109.5 .
H00N C00N H00P 109.5 .
H00O C00N H00P 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N001 C002 1.4429(17) .
N001 C004 1.4172(18) .
N001 C006 1.4138(19) .
C002 C003 1.386(2) .
C002 C00E 1.388(2) .
C003 H003 0.9300 .
C003 C007 1.382(2) .
C004 C008 1.408(2) .
C004 C00C 1.391(2) .
C005 C007 1.398(2) .
C005 C00A 1.433(2) .
C005 C00D 1.393(2) .
C006 C009 1.404(2) .
C006 C00B 1.401(2) .
C007 H007 0.9300 .
C008 C00F 1.387(2) .
C008 C00G 1.519(2) .
C009 C00G 1.528(2) .
C009 C00I 1.391(2) .
C00A C00A 1.202(3) 3_765
C00B H00B 0.9300 .
C00B C00J 1.384(2) .
C00C H00C 0.9300 .
C00C C00H 1.390(2) .
C00D H00D 0.9300 .
C00D C00E 1.384(2) .
C00E H00E 0.9300 .
C00F H00F 0.9300 .
C00F C00K 1.388(2) .
C00G C00M 1.549(3) .
C00G C00N 1.530(2) .
C00H H00H 0.9300 .
C00H C00K 1.376(2) .
C00I H00I 0.9300 .
C00I C00L 1.385(2) .
C00J H00J 0.9300 .
C00J C00L 1.380(2) .
C00K H00K 0.9300 .
C00L H00L 0.9300 .
C00M H00A 0.9600 .
C00M H00G 0.9600 .
C00M H00M 0.9600 .
C00N H00N 0.9600 .
C00N H00O 0.9600 .
C00N H00P 0.9600 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339834
