Alkyl-substituted bis(4-((9H-fluoren-9-ylidene)methyl)phenyl)thiophenes: weakening of intermolecular interactions and additive-assisted crystallization
Sonina, Alina A.; Becker, Christina S.; Kuimov, Anatoly D.; Shundrina, Inna K.; Komarov, Vladislav Yu.; Kazantsev, Maxim S.; CrystEngComm 23 (2021) 2654–2664; doi:10.1039/D0CE01794A

data_7242319
_publ_section_title
;
 Alkyl-substituted bis(4-((9H-fluoren-9-ylidene)methyl)phenyl)thiophenes:
 weakening of intermolecular interactions and additive-assisted
 crystallization
;
_journal_issue                   14
_journal_name_full               CrystEngComm
_journal_page_first              2654
_journal_page_last               2664
_journal_paper_doi               10.1039/D0CE01794A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C52 H44 S'
_chemical_formula_sum            'C52 H44 S'
_chemical_formula_weight         700.93
_chemical_melting_point          499,15
_chemical_name_systematic
2,5-bis(4-((2,7-diethyl-9H-fluoren-9-ylidene)methyl)phenyl)thiophene
_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             2021-01-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-01-28 deposited with the CCDC.	2021-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.099(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.581(6)
_cell_length_b                   9.216(3)
_cell_length_c                   25.101(9)
_cell_measurement_reflns_used    6920
_cell_measurement_temperature    200(1)
_cell_measurement_theta_max      19.55
_cell_measurement_theta_min      2.59
_cell_volume                     3836(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(1)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'Bruker APEXII CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            30271
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        21.036
_diffrn_reflns_theta_max         21.036
_diffrn_reflns_theta_min         2.033
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.7203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0779 before and 0.0703 after correction.
The Ratio of minimum to maximum transmission is 0.8355.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_description       needle
_exptl_crystal_F_000             1488
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2'
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Twinning involves inversion, so Flack parameter cannot be determined
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     960
_refine_ls_number_reflns         8241
_refine_ls_number_restraints     990
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0515P)^2^+1.6380P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1203
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                7315
_reflns_number_total             8241
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01794a2.cif
_cod_data_source_block           C2-BFMPT
_cod_depositor_comments
'Adding full bibliography for 7242319--7242322.cif.'
_cod_database_code               7242319
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.889
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.55(15)
 0.40(5) 0.06(13) -0.01(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C15_12-C17_12 = C17_12-C25_12 = C27_12-C27_12 = C28_12-C17_12 = C18A_12-
 C17_12 = C18B_12-C27_12 = C27_12-?
 C15_21-C17_21 = C17_21-C25_21 = C27_21-C27_21 = C28_21-C17_21 = C18A_21-
 C17_21 = C18B_21-C27_21 = C27_21-?
 C15_22-C17_22 = C17_22-C18_22 = C25_22-C27_22 = C27_22-C17_22 = C17_22-C27_22
 = C28A_22-C27_22 = C28B_22-?
 C15_11-C17_11 = C17_11-C25_11 = C27_11-C27_11 = C17_11-C18A_11 = C17_11-
 C18B_11 = C27_11-C28A_11 = C27_11-C28B_11
 1.54 with sigma of 0.001
 C15_12-C25_12 = C28_12-C15_12 = C18A_12-C25_12 = C15_12-C18B_12 = C25_12-?
 C15_21-C25_21 = C28_21-C15_21 = C18A_21-C25_21 = C15_21-C18B_21 = C25_21-?
 C15_22-C18_22 = C25_22-C15_22 = C25_22-C28A_22 = C15_22-C25_22 = C28B_22-?
 C15_11-C25_11 = C15_11-C18A_11 = C25_11-C28A_11 = C15_11-C18B_11 = C25_11-
 C28B_11
 2.52 with sigma of 0.002
 S1'_10-C5'_10 \\sim S1'_10-C2'_10
 S1'_20-C5'_20 \\sim S1'_20-C2'_20
 with sigma of 0.005
 C4'_10-C5'_10 \\sim C2'_10-C3'_10
 C4'_20-C5'_20 \\sim C2'_20-C3'_20
 with sigma of 0.005
 C3'_10-C4'_10
 C3'_20-C4'_20
 with sigma of 0.005
4. Uiso/Uaniso restraints and constraints
C18B_11 \\sim C18A_11: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
C28B_11 \\sim C28A_11: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
C18B_21 \\sim C18A_21: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(H27C)=Sof(H27D)=Sof(C28B)=Sof(H28D)=Sof(H28E)=Sof(H28F)=1-FVAR(1)
 Sof(H27A)=Sof(H27B)=Sof(C28A)=Sof(H28A)=Sof(H28B)=Sof(H28C)=FVAR(1)
 Sof(H27C)=Sof(H27D)=Sof(C28B)=Sof(H28D)=Sof(H28E)=Sof(H28F)=1-FVAR(2)
 Sof(H27A)=Sof(H27B)=Sof(C28A)=Sof(H28A)=Sof(H28B)=Sof(H28C)=FVAR(2)
 Sof(H17C)=Sof(H17D)=Sof(C18B)=Sof(H18D)=Sof(H18E)=Sof(H18F)=1-FVAR(3)
 Sof(H17A)=Sof(H17B)=Sof(C18A)=Sof(H18A)=Sof(H18B)=Sof(H18C)=FVAR(3)
 Sof(H17C)=Sof(H17D)=Sof(C18B)=Sof(H18A)=Sof(H18B)=Sof(H18C)=1-FVAR(4)
 Sof(H17A)=Sof(H17B)=Sof(C18A)=Sof(H18D)=Sof(H18E)=Sof(H18F)=FVAR(4)
 Sof(H17C)=Sof(H17D)=Sof(C18B)=Sof(H18D)=Sof(H18E)=Sof(H18F)=1-FVAR(5)
 Sof(H17A)=Sof(H17B)=Sof(C18A)=Sof(H18A)=Sof(H18B)=Sof(H18C)=FVAR(5)
7.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C17(H17C,H17D), C27(H27A,H27B), C17(H17A,H17B), C17(H17C,
 H17D), C27(H27A,H27B), C17(H17A,H17B), C27(H27A,H27B), C27(H27C,H27D),
 C17(H17A,H17B), C17(H17C,H17D), C27(H27A,H27B), C27(H27C,H27D)
7.b Me refined with riding coordinates:
 C18A(H18A,H18B,H18C), C18B(H18D,H18E,H18F), C28(H28A,H28B,H28C), C18B(H18A,
 H18B,H18C), C18A(H18D,H18E,H18F), C28(H28A,H28B,H28C), C18(H18A,H18B,H18C),
 C28A(H28A,H28B,H28C), C28B(H28D,H28E,H28F), C18A(H18A,H18B,H18C), C18B(H18D,
 H18E,H18F), C28A(H28A,H28B,H28C), C28B(H28D,H28E,H28F)
7.c Aromatic/amide H refined with riding coordinates:
 C3'(H3'), C4'(H4'), C16'(H16'), C12'(H12'), C13'(H13'), C15'(H15'),
 C25'(H25'), C23'(H23'), C22'(H22'), C26'(H26'), C1(H1), C13(H13), C14(H14),
 C16(H16), C23(H23), C24(H24), C26(H26), C3'(H3'), C4'(H4'), C12'(H12'),
 C16'(H16'), C15'(H15'), C13'(H13'), C23'(H23'), C25'(H25'), C26'(H26'),
 C22'(H22'), C1(H1), C13(H13), C14(H14), C16(H16), C23(H23), C24(H24), C26(H26),
  C1(H1), C13(H13), C14(H14), C16(H16), C23(H23), C24(H24), C26(H26), C1(H1),
 C13(H13), C14(H14), C16(H16), C23(H23), C24(H24), C26(H26)
7.d Fitted hexagon refined as free rotating group:
 C16'(C11',C12',C13',C14',C15'), C25'(C24',C23',C22',C21',C26'), C12'(C11',
 C16',C15',C14',C13'), C23'(C24',C25',C26',C21',C22')
;
_shelx_res_checksum              65572
_shelx_hkl_checksum              35875
_olex2_submission_special_instructions 'No special instructions were received'