Novel TCNQ-stacking motifs in (12-crown-4)-complexes of alkali metal TCNQ salts
Yan, Bingjia; Horton, Peter N.; Weston, Simon C.; Russell, Andrea E.; Grossel, Martin C.; CrystEngComm 23 (2021) 6755–6760; doi:10.1039/D1CE01075A

data_7243509
_publ_section_title
;
 Novel TCNQ-stacking motifs in (12-crown-4)-complexes of alkali metal TCNQ
 salts
;
_journal_issue                   38
_journal_name_full               CrystEngComm
_journal_page_first              6755
_journal_page_last               6760
_journal_paper_doi               10.1039/D1CE01075A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         '0.5(C32 H64 Li2 O16), C12 H4 N4'
_chemical_formula_sum            'C28 H36 Li N4 O8'
_chemical_formula_weight         563.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-08-06 deposited with the CCDC.	2021-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.541(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8468(3)
_cell_length_b                   20.5523(4)
_cell_length_c                   8.3102(2)
_cell_measurement_reflns_used    8113
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.3380
_cell_measurement_theta_min      5.2250
_cell_volume                     2877.20(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.79a (Rigaku OD, 2020)'
_computing_data_collection
'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.40.79a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 22.2222
_diffrn_detector_type            'Rigaku HG Saturn944+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -130.00  50.00   2.00   15.00    --  -40.00  60.00  90.00   90
  2  \w   -130.00  50.00   2.00   15.00    --  -40.00  60.00   0.00   90
  3  \w    -88.00   6.00   2.00   15.00    --  -40.00  30.00 270.00   47
  4  \w   -130.00 -62.00   2.00   15.00    --  -40.00  60.00 180.00   34
  5  \w   -120.00 -88.00   2.00   15.00    --  -40.00   0.00 270.00   16
  6  \w   -180.00   0.00   2.00   60.00    --  -90.00  30.00 270.00   90
  7  \w   -180.00   0.00   2.00   60.00    --  -90.00  60.00 120.00   90
  8  \w   -180.00   0.00   2.00   60.00    --  -90.00  60.00 240.00   90
  9  \w   -180.00   0.00   2.00   60.00    --  -90.00  10.00   0.00   90
 10  \w   -180.00   0.00   2.00   60.00    --  -90.00  60.00  90.00   90
 11  \w   -180.00   0.00   2.00   60.00    --  -90.00  50.00   0.00   90
 12  \w   -180.00   0.00   2.00   60.00    --  -90.00  60.00 270.00   90
 13  \w   -179.00 -11.00   2.00   60.00    --  -90.00  20.00 180.00   84
 14  \w   -179.00 -21.00   2.00   60.00    --  -90.00  60.00 180.00   79
 15  \w   -180.00 -48.00   2.00   60.00    --  -90.00  60.00   0.00   66
 16  \w   -180.00 -80.00   2.00   60.00    --  -90.00  20.00  90.00   50
 17  \w   -165.00-105.00   2.00   60.00    --  -90.00  50.00  90.00   30
;
_diffrn_measurement_device       'four-circle quarter \c goniometer'
_diffrn_measurement_device_type
'Rigaku 007HF equipped with Varimax confocal mirrors and an AFC11 goniometer and HG Saturn 944+ detector'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0795681000
_diffrn_orient_matrix_UB_12      0.0252605000
_diffrn_orient_matrix_UB_13      0.0679716000
_diffrn_orient_matrix_UB_21      0.0423778000
_diffrn_orient_matrix_UB_22      -0.0607343000
_diffrn_orient_matrix_UB_23      -0.0659682000
_diffrn_orient_matrix_UB_31      0.0154767000
_diffrn_orient_matrix_UB_32      0.0359811000
_diffrn_orient_matrix_UB_33      -0.1592703000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            24070
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.564
_diffrn_reflns_theta_max         66.564
_diffrn_reflns_theta_min         3.392
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rigaku 007HF'
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    0.788
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.79a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic dark blue'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       plate
_exptl_crystal_F_000             1196
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.00033(8)
_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   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         2545
_refine_ls_number_restraints     474
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0463P)^2^+1.3963P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1014
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1944
_reflns_number_total             2545
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01075a2.cif
_cod_data_source_block           MCG1
_cod_depositor_comments
'Adding full bibliography for 7243509--7243513.cif.'
_cod_database_code               7243509
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C12H4N4 C8H16O4 Li'
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.764
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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
All non-hydrogen atoms have similar U: within 2A with sigma of 0.02 and sigma
for terminal atoms of 0.04 within 2A
3. Same fragment restrains
{C11, C12, C13, C14, C15, C16, C17, C18, O11, O12, O13, O14} sigma for 1-2:
0.02, 1-3: 0.04
as in
{C21, C22, C23, C24, C25, C26, C27, C28, O21, O22, O23, O24}
4. Others
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23A)=
 Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(C26)=
 Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(C28)=Sof(H28A)=Sof(H28B)=
 Sof(O21)=Sof(O22)=Sof(O23)=Sof(O24)=1-FVAR(1)
 Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C13)=Sof(H13A)=
 Sof(H13B)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C16)=
 Sof(H16A)=Sof(H16B)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(C18)=Sof(H18A)=Sof(H18B)=
 Sof(O11)=Sof(O12)=Sof(O13)=Sof(O14)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,
 H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C21(H21A,H21B),
 C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B),
  C27(H27A,H27B), C28(H28A,H28B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
;
_shelx_res_checksum              86106
_shelx_hkl_checksum              76590
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_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 1.472
_oxdiff_exptl_absorpt_empirical_full_min 0.589