Analysis of Solid-State Emission of the p-Bis(2,2-dicyanovinyl)benzene Analogue through Combined X-ray, Synchrotron, and Microcrystal Electron Diffraction
Deka, Poonam; Jaiswal, Shilpi; Sarma, Parishmita; Bora, Debajit; Nakane, Takanori; Kawamoto, Akihiro; Kurisu, Genji; Mahanta, Sanjeev Pran; Patra, Abhijit; Ichiyanagi, Kouhei; Sasaki, Toshiyuki; Thakuria, Ranjit; Crystal Growth & Design 24 (2024) 7222–7234; doi:10.1021/acs.cgd.4c00856

data_3000476
_publ_section_title
;
 Analysis of Solid-State Emission of the p-Bis(2,2-dicyanovinyl)benzene
 Analogue through Combined X-ray, Synchrotron, and Microcrystal Electron
 Diffraction
;
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              7222
_journal_page_last               7234
_journal_paper_doi               10.1021/acs.cgd.4c00856
_journal_volume                  24
_journal_year                    2024
_chemical_formula_moiety         '2(O), C20 H10 N4'
_chemical_formula_sum            'C20 H10 N4 O2'
_chemical_formula_weight         338.32
_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     dual
_audit_creation_date             2024-01-09
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.318(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.7388(2)
_cell_length_b                   11.9046(5)
_cell_length_c                   40.4205(19)
_cell_measurement_reflns_used    5277
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.0770
_cell_measurement_theta_min      2.2590
_cell_volume                     1797.60(15)
_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    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Dectris Eiger X 1M'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -90.00  89.80   0.20    2.50    --   25.00  45.00   0.00  899
  2  \w    -90.00  89.80   0.20    2.50    --   25.00  45.00  90.00  899
  3  \w    -90.00  89.80   0.20    2.50    --   25.00  45.00 180.00  899
  4  \w    -90.00  89.80   0.20    2.50    --   25.00  45.00 270.00  899
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1314402000
_diffrn_orient_matrix_UB_12      -0.0199465000
_diffrn_orient_matrix_UB_13      0.0153815000
_diffrn_orient_matrix_UB_21      -0.1498829000
_diffrn_orient_matrix_UB_22      0.0186689000
_diffrn_orient_matrix_UB_23      0.0128915000
_diffrn_orient_matrix_UB_31      -0.0865522000
_diffrn_orient_matrix_UB_32      -0.0625306000
_diffrn_orient_matrix_UB_33      -0.0010752000
_diffrn_radiation_monochromator  'Si(111) Channel Cut'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.812
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            8407
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        29.157
_diffrn_reflns_theta_max         30.486
_diffrn_reflns_theta_min         1.728
_diffrn_source                   'Synchrotron radiation SPring-8 BL40XU'
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35037
_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            yellow
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.655
_refine_diff_density_rms         0.198
_refine_ls_abs_structure_details
;
 Flack x determined using 1274 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   10.0(10)
_refine_ls_extinction_coef       0.055(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.667
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         8407
_refine_ls_number_restraints     485
_refine_ls_restrained_S_all      1.639
_refine_ls_R_factor_all          0.2474
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4468
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_full    0.933
_reflns_Friedel_fraction_max     0.919
_reflns_number_gt                4134
_reflns_number_total             8407
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9363\% 
 around [0.92 0.00 -0.38] (reciprocal) or [1.00 0.00 0.00] (direct)
;
_cod_data_source_file            bp-1_twin.cif
_cod_data_source_block           bp-1_twin
_cod_depositor_comments
'Releasing structure 3000476 into public domain as published material.'
_cod_database_code               3000476
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H20N8
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.643(6)
 0.357(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Uiso/Uaniso restraints and constraints
N007 \\sim C26 \\sim H20 \\sim C27 \\sim C00M \\sim H25 \\sim H00O \\sim C20
\\sim H00Q \\sim C011 \\sim O4 \\sim O3 \\sim C00H \\sim N00X \\sim N005 \\sim
O5 \\sim H00U \\sim C00Z \\sim C014 \\sim C00V \\sim C013 \\sim N00I \\sim C00A
\\sim O1 \\sim O2 \\sim C001 \\sim H00M \\sim C00S \\sim C21 \\sim C00J \\sim
C00T \\sim C22 \\sim C00R \\sim C00O \\sim H23 \\sim H24 \\sim H21 \\sim C00K
\\sim C00N \\sim C00W \\sim C012 \\sim C00Q \\sim H010 \\sim O6 \\sim N00P:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.01 within 2A
Uanis(C22) \\sim Ueq, Uanis(C00O) \\sim Ueq, Uanis(C001) \\sim Ueq, Uanis(C00S)
\\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C00J) \\sim Ueq, Uanis(C00T) \\sim Ueq,
Uanis(C00R) \\sim Ueq, Uanis(C00K) \\sim Ueq, Uanis(C00N) \\sim Ueq,
Uanis(C00W) \\sim Ueq, Uanis(C012) \\sim Ueq, Uanis(C00Q) \\sim Ueq,
Uanis(N00P) \\sim Ueq, Uanis(C011) \\sim Ueq, Uanis(N007) \\sim Ueq, Uanis(C26)
\\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C00M) \\sim Ueq, Uanis(C20) \\sim Ueq,
Uanis(C00H) \\sim Ueq, Uanis(N00X) \\sim Ueq, Uanis(N005) \\sim Ueq,
Uanis(C00Z) \\sim Ueq, Uanis(C014) \\sim Ueq, Uanis(C00V) \\sim Ueq,
Uanis(C013) \\sim Ueq, Uanis(N00I) \\sim Ueq, Uanis(C00A) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.005
Uanis(C25) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.005
Uanis(C014) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.001
Uanis(C00Y) = Uanis(C018) = Uanis(C003) = Uanis(C001) = Uanis(C00T) =
Uanis(C00A) = Uanis(C01C) = Uanis(C014) = Uanis(C01B) = Uanis(C00Z) =
Uanis(C00S) = Uanis(C00L)
Uanis(C00M) = Uanis(C22) = Uanis(C20) = Uanis(C21) = Uanis(C00W) = Uanis(C00N)
Uanis(C25) = Uanis(C00J) = Uanis(C00K) = Uanis(C00U) = Uanis(C015) =
Uanis(C00R) = Uanis(C010) = Uanis(C00V) = Uanis(C26) = Uanis(C00Q) =
Uanis(C011) = Uanis(C012)
4. Rigid body (RIGU) restrains
 H00O, N007, C26, H20, C27, C00M, H25, C20, H00Q, C011, O4, O3, C00H, N00X,
 N005, O5, H00U, C00Z, C014, C00V, C013, N00I, C00A, C012, O1, O2, C001, H00M,
 C00S, C21, C00J, C00T, C22, C00R, C00O, H23, H24, H21, C00K, C00N, C00W, C00Q,
 H010, O6, N00P
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
5. Others
 1*[Sof(O2)]+1*[Sof(O4)]+1*[Sof(O6)]+1*[Sof(O9)]+1*[Sof(O11)]+1*[Sof(O13)]+1*
 [Sof(O14)]=2 with esd of 0.001
 1*[Sof(O1)]+1*[Sof(O3)]+1*[Sof(O5)]+1*[Sof(O7)]+1*[Sof(O8)]+1*[Sof(O10)]+1*
 [Sof(O12)]=2 with esd of 0.001
6.a Aromatic/amide H refined with riding coordinates:
 C27(H27), C24(H24), C26(H26), C21(H21), C23(H23), C20(H20), C25(H25),
 C00H(H00H), C00J(H00J), C00M(H00M), C00N(H00N), C00O(H00O), C00Q(H00Q),
 C00R(H00R), C00U(H00U), C010(H010), C012(H012), C016(H016), C017(H017),
 C01A(H01A)
;
_shelx_res_checksum              80096
_shelx_hkl_checksum              21278
_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 4.920
_oxdiff_exptl_absorpt_empirical_full_min 0.241
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2