Comparing the structures and photophysical properties of two charge transfer co-crystals.
Abou Taka, Ali; Reynolds, 3rd, Joseph E; Cole-Filipiak, Neil C; Shivanna, Mohana; Yu, Christine J.; Feng, Patrick; Allendorf, Mark D.; Ramasesha, Krupa; Stavila, Vitalie; McCaslin, Laura M.; Physical chemistry chemical physics : PCCP 25 (2023) 27065–27074; doi:10.1039/d3cp03720g

data_7247439
_publ_section_title
;
 Comparing the structures and photophysical properties of two charge
 transfer co-crystals.
;
_journal_issue                   40
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              27065
_journal_page_last               27074
_journal_paper_doi               10.1039/d3cp03720g
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C10 H2 N4, C17 H13 N'
_chemical_formula_sum            'C27 H15 N5'
_chemical_formula_weight         409.44
_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     direct
_audit_creation_date             2022-06-28
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-08-03 deposited with the CCDC.	2023-09-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.283(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7312(3)
_cell_length_b                   36.6599(13)
_cell_length_c                   9.5150(4)
_cell_measurement_reflns_used    2625
_cell_measurement_temperature    99.95(10)
_cell_measurement_theta_max      68.1260
_cell_measurement_theta_min      4.7860
_cell_volume                     2253.79(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2358
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.972
_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    -55.00  32.00   1.00   22.50    --  -42.47  38.00   0.00   87
  2  \w    -76.00  26.00   1.00   22.50    --  -42.47  19.00 -90.00  102
  3  \w     73.00 174.00   1.00   65.00    --  102.45  61.00 -60.00  101
  4  \w    123.00 155.00   1.00   65.00    --  102.45 125.00 -60.00   32
  5  \w    101.00 132.00   1.00   65.00    --  102.45 -61.00-150.00   31
  6  \w     30.00  77.00   1.00   65.00    --  102.45 -61.00-150.00   47
  7  \w     74.00 160.00   1.00   65.00    --  102.45  61.00  30.00   86
  8  \w    112.00 143.00   1.00   65.00    --  102.45  77.00 -30.00   31
  9  \w     98.00 135.00   1.00   65.00    --  102.45 125.00 -30.00   37
 10  \w    138.00 164.00   1.00   65.00    --  102.45 125.00 -30.00   26
 11  \w    132.00 178.00   1.00   65.00    --  102.45  77.00 120.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1730409000
_diffrn_orient_matrix_UB_12      0.0287689000
_diffrn_orient_matrix_UB_13      -0.0304468000
_diffrn_orient_matrix_UB_21      0.0994812000
_diffrn_orient_matrix_UB_22      0.0173632000
_diffrn_orient_matrix_UB_23      0.1505777000
_diffrn_orient_matrix_UB_31      0.1297588000
_diffrn_orient_matrix_UB_32      0.0251040000
_diffrn_orient_matrix_UB_33      -0.0690603000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8966
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.129
_diffrn_reflns_theta_min         4.825
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.586
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
_exptl_crystal_preparation       'cryoloop with paratone oil'
_exptl_crystal_recrystallization_method 'slow evaporation / 1:1 DMF:MeCN'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.037
_refine_diff_density_max         0.940
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4325
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1331
_refine_ls_R_factor_gt           0.1237
_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^)+(0.1316P)^2^+8.6783P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3330
_refine_ls_wR_factor_ref         0.3397
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3702
_reflns_number_total             4325
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cp03720g2.cif
_cod_data_source_block           Npe-TCNB
_cod_depositor_comments
'Adding full bibliography for 7247438--7247439.cif.'
_cod_database_code               7247439
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         N5C26H15
_chemical_oxdiff_usercomment     '1:1 acetonitrile:DMF'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
N1 \\sim N1A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
C3 \\sim C6 \\sim C3A \\sim C6A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
C1 \\sim C2 \\sim C4 \\sim C5 \\sim C1A \\sim C2A \\sim C4A \\sim C5A: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
3. Others
 Sof(H7B)=Sof(N1A)=Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(C4A)=
 Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=1-FVAR(1)
 Sof(H7A)=Sof(N1)=Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(C4)=Sof(H4)=
 Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C22(H22), C27(H27), C7(H7B), C7(H7A), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15), C16(H16), C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C1A(H1A),
  C2A(H2A), C4A(H4A), C5A(H5A), C6A(H6A)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              25644
_shelx_fab_checksum              21743
_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 1.399
_oxdiff_exptl_absorpt_empirical_full_min 0.802