Five Shades of Green: Substituent Influence on the (Spectro-) Electrochemical Properties of Diferrocenylphenyl Methylium Dyes
Casper, Larissa Alina; Ebel, Viktoria; Linseis, Michael; Winter, Rainer; Dalton Transactions  (2021) –; doi:10.1039/D1DT03009D

data_7708520
_publ_section_title
;
 Five Shades of Green: Substituent Influence on the (Spectro-)
 Electrochemical Properties of Diferrocenylphenyl Methylium Dyes
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT03009D
_journal_year                    2021
_chemical_formula_moiety         'C28 H25 Fe2 O, 2(C24 H10.5 B F18 O)'
_chemical_formula_sum            'C76 H46 B2 F36 Fe2 O3'
_chemical_formula_weight         1824.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-16
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_audit_update_record
;
2021-07-09 deposited with the CCDC.	2021-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                95.572(3)
_cell_angle_beta                 99.689(3)
_cell_angle_gamma                101.636(3)
_cell_formula_units_Z            2
_cell_length_a                   12.8380(4)
_cell_length_b                   15.1737(5)
_cell_length_c                   23.1393(8)
_cell_measurement_reflns_used    37930
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.19
_cell_measurement_theta_min      1.80
_cell_volume                     4311.7(3)
_computing_cell_refinement
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_data_reduction
;
X-Area Integrate 1.74.2.0 (STOE, 2018)
X-Area LANA 1.75.3.0 (STOE, 2018)
;
_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_temperature      100.0
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
 478 frames, detector distance = 80 mm
;
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            41329
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.850
_diffrn_reflns_theta_min         2.027
_exptl_absorpt_coefficient_mu    0.457
_exptl_absorpt_correction_T_max  0.9427
_exptl_absorpt_correction_T_min  0.2308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(\m~2~-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       0.0049(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1285
_refine_ls_number_reflns         18527
_refine_ls_number_restraints     212
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1164
_refine_ls_R_factor_gt           0.0619
_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^)+(0.1028P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1592
_refine_ls_wR_factor_ref         0.1883
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10044
_reflns_number_total             18527
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt03009d2.cif
_cod_data_source_block           lc45
_cod_database_code               7708520
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.935
_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. Restrained distances
 F6-C36 \\sim F6A-C36A
 with sigma of 0.02
 F1-C35 \\sim F1A-C35A
 with sigma of 0.02
 C29-C30 \\sim C29-C30A
 with sigma of 0.02
 C29-C34 \\sim C29-C34A
 with sigma of 0.02
 C29-B1 \\sim C29-B1
 with sigma of 0.02
 C30-C31 \\sim C30A-C31A
 with sigma of 0.02
 C34-C33 \\sim C34A-C33A
 with sigma of 0.02
 C31-C32 \\sim C31A-C32A
 with sigma of 0.02
 C31-C35 \\sim C31A-C35A
 with sigma of 0.02
 C32-C33 \\sim C32A-C33A
 with sigma of 0.02
 C33-C36 \\sim C33A-C36A
 with sigma of 0.02
 C35-F2 \\sim C35A-F2A
 with sigma of 0.02
 C35-F3 \\sim C35A-F3A
 with sigma of 0.02
 F5-C36 \\sim F5A-C36A
 with sigma of 0.02
 C36-F4 \\sim C36A-F4A
 with sigma of 0.02
 F6-C33 \\sim F6A-C33A
 with sigma of 0.04
 F6-F5 \\sim F6A-F5A
 with sigma of 0.04
 F6-F4 \\sim F6A-F4A
 with sigma of 0.04
 F1-C31 \\sim F1A-C31A
 with sigma of 0.04
 F1-F2 \\sim F1A-F2A
 with sigma of 0.04
 F1-F3 \\sim F1A-F3A
 with sigma of 0.04
 C29-C31 \\sim C29-C31A
 with sigma of 0.04
 C29-C33 \\sim C29-C33A
 with sigma of 0.04
 C30-C34 \\sim C30A-C34A
 with sigma of 0.04
 C30-C32 \\sim C30A-C32A
 with sigma of 0.04
 C30-C35 \\sim C30A-C35A
 with sigma of 0.04
 C30-B1 \\sim C30A-B1
 with sigma of 0.04
 C34-C32 \\sim C34A-C32A
 with sigma of 0.04
 C34-B1 \\sim C34A-B1
 with sigma of 0.04
 C34-C36 \\sim C34A-C36A
 with sigma of 0.04
 C31-C33 \\sim C31A-C33A
 with sigma of 0.04
 C31-F2 \\sim C31A-F2A
 with sigma of 0.04
 C31-F3 \\sim C31A-F3A
 with sigma of 0.04
 C32-C35 \\sim C32A-C35A
 with sigma of 0.04
 C32-C36 \\sim C32A-C36A
 with sigma of 0.04
 C33-F5 \\sim C33A-F5A
 with sigma of 0.04
 C33-F4 \\sim C33A-F4A
 with sigma of 0.04
 F5-F4 \\sim F5A-F4A
 with sigma of 0.04
 F2-F3 \\sim F2A-F3A
 with sigma of 0.04
 F21-C59 \\sim F21A-C59
 with sigma of 0.02
 F20-C59 \\sim F20A-C59
 with sigma of 0.02
 F19-C59 \\sim F19A-C59
 with sigma of 0.02
 F22-C60 \\sim F22A-C60
 with sigma of 0.02
 F24-C60 \\sim F24A-C60
 with sigma of 0.02
 F23-C60 \\sim F23A-C60
 with sigma of 0.02
 F9-C52 \\sim F7A-C52
 with sigma of 0.02
 C52-F7 \\sim C52-F8A
 with sigma of 0.02
 C52-F8 \\sim C52-F9A
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C29, C30, C31, C32, C33, C34
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F1, F2, F3, C35
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F4, F5, F6, C36
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C29, C30A, C31A, C32A, C33A, C34A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F1A, F2A, F3A, C35A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F4A, F5A, F6A, C36A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C59, F19, F20, F21
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F22, F23, F24
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F22A, F23A, F24A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C29, B1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=Sof(C30A)=Sof(H30A)=
 Sof(C31A)=Sof(C32A)=Sof(H32A)=Sof(C33A)=Sof(C34A)=Sof(H34A)=Sof(C35A)=
 Sof(C36A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=Sof(C30)=Sof(H30)=Sof(C31)=
 Sof(C32)=Sof(H32)=Sof(C33)=Sof(C34)=Sof(H34)=Sof(C35)=Sof(C36)=FVAR(1)
 Sof(F19A)=Sof(F20A)=Sof(F21A)=1-FVAR(2)
 Sof(F19)=Sof(F20)=Sof(F21)=FVAR(2)
 Sof(F22A)=Sof(F23A)=Sof(F24A)=1-FVAR(3)
 Sof(F22)=Sof(F23)=Sof(F24)=FVAR(3)
 Sof(F7A)=Sof(F8A)=Sof(F9A)=1-FVAR(4)
 Sof(F7)=Sof(F8)=Sof(F9)=FVAR(4)
 Fixed Uiso: H2B(0.25)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11),
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20),
  C21(H21), C23(H23), C24(H24), C26(H26), C27(H27), C38(H38), C40(H40),
 C42(H42), C46(H46), C48(H48), C50(H50), C30(H30), C32(H32), C34(H34),
 C30A(H30A), C32A(H32A), C34A(H34A), C54(H54), C56(H56), C58(H58), C62(H62),
 C64(H64), C66(H66), C70(H70), C72(H72), C74(H74)
5.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              28272
_shelx_hkl_checksum              15981
_shelx_fab_checksum              48967
_olex2_submission_special_instructions 'No special instructions were received'