Fusing pyrene and ferrocene into a chiral, redox-active triangle.
Metzelaars, Marvin; Sanz, Sergio; Rawson, Jeff; Hartmann, Rudolf; Schneider, Claus M.; Kögerler, Paul; Chemical communications (Cambridge, England) 57 (2021) 6660–6663; doi:10.1039/d1cc02191e

data_7128462
_publ_section_title
;
 Fusing pyrene and ferrocene into a chiral, redox-active triangle.
;
_journal_issue                   54
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6660
_journal_page_last               6663
_journal_paper_doi               10.1039/d1cc02191e
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C78 H48 Fe3, 5(C4 H8 O)'
_chemical_formula_sum            'C98 H88 Fe3 O5'
_chemical_formula_weight         1513.23
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-09 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                78.866(2)
_cell_angle_beta                 79.702(2)
_cell_angle_gamma                87.174(2)
_cell_formula_units_Z            2
_cell_length_a                   11.4240(3)
_cell_length_b                   17.7656(4)
_cell_length_c                   18.4462(3)
_cell_measurement_reflns_used    19668
_cell_measurement_temperature    100.3(3)
_cell_measurement_theta_max      29.0320
_cell_measurement_theta_min      3.4870
_cell_volume                     3613.67(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.3(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4623
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.887
_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    -42.00  66.00   0.75   22.50    --  -10.54  77.00   0.00  144
  2  \w    -42.00  66.00   0.75   22.50    --  -10.54  77.00-120.00  144
  3  \w    -22.00  87.50   0.75   22.50    --   11.01  77.00 -90.00  146
  4  \w    -22.00  87.50   0.75   22.50    --   11.01  77.00 150.00  146
  5  \w    -84.00  14.25   0.75   22.50    --  -10.54 -38.00 -60.00  131
  6  \w    -19.00  52.25   0.75   22.50    --   11.01 -99.00 120.00   95
  7  \w    -19.00  52.25   0.75   22.50    --   11.01 -99.00-150.00   95
  8  \w    -20.00  17.50   0.75   22.50    --   11.01 -99.00   0.00   50
  9  \w    -19.00  52.25   0.75   22.50    --   11.01 -99.00 150.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0501712000
_diffrn_orient_matrix_UB_12      -0.0205024000
_diffrn_orient_matrix_UB_13      0.0119238000
_diffrn_orient_matrix_UB_21      0.0330217000
_diffrn_orient_matrix_UB_22      0.0343493000
_diffrn_orient_matrix_UB_23      -0.0097135000
_diffrn_orient_matrix_UB_31      -0.0193799000
_diffrn_orient_matrix_UB_32      0.0074796000
_diffrn_orient_matrix_UB_33      0.0366952000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            80096
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.761
_diffrn_reflns_theta_min         3.408
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.472
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_crystal_colour            'clear reddish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       plate
_exptl_crystal_F_000             1588
_exptl_crystal_recrystallization_method
'crystals grown from THF using vapor diffusion method with cyclohexane as countersolvent'
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.182
_refine_diff_density_max         0.815
_refine_diff_density_min         -0.911
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1149
_refine_ls_number_reflns         18292
_refine_ls_number_restraints     704
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0551
_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^)+(0.0472P)^2^+3.9500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1349
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12738
_reflns_number_total             18292
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02191e6.cif
_cod_data_source_block           mm259
_cod_depositor_comments
'Adding full bibliography for 7128459--7128462.cif.'
_cod_original_cell_volume        3613.68(14)
_cod_database_code               7128462
_shelx_estimated_absorpt_t_max   0.890
_shelx_estimated_absorpt_t_min   0.776
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 O1D-C4D \\sim O1E-C4E
 with sigma of 0.02
 O1D-C1D \\sim O1E-C1E
 with sigma of 0.02
 C3D-C4D \\sim C3E-C4E
 with sigma of 0.02
 C3D-C2D \\sim C3E-C2E
 with sigma of 0.02
 C1D-C2D \\sim C1E-C2E
 with sigma of 0.02
 O1D-C3D \\sim O1E-C3E
 with sigma of 0.04
 O1D-C2D \\sim O1E-C2E
 with sigma of 0.04
 C3D-C1D \\sim C3E-C1E
 with sigma of 0.04
 C4D-C1D \\sim C4E-C1E
 with sigma of 0.04
 C4D-C2D \\sim C4E-C2E
 with sigma of 0.04
 O1F-C1F \\sim O1G-C1G
 with sigma of 0.02
 O1F-C4F \\sim O1G-C4G
 with sigma of 0.02
 C3F-C2F \\sim C3G-C2G
 with sigma of 0.02
 C3F-C4F \\sim C3G-C4G
 with sigma of 0.02
 C2F-C1F \\sim C2G-C1G
 with sigma of 0.02
 O1F-C3F \\sim O1G-C3G
 with sigma of 0.04
 O1F-C2F \\sim O1G-C2G
 with sigma of 0.04
 C3F-C1F \\sim C3G-C1G
 with sigma of 0.04
 C2F-C4F \\sim C2G-C4G
 with sigma of 0.04
 C1F-C4F \\sim C1G-C4G
 with sigma of 0.04
 O1H-C1H \\sim O1I-C1I
 with sigma of 0.02
 O1H-C4H \\sim O1I-C4I
 with sigma of 0.02
 C2H-C1H \\sim C2I-C1I
 with sigma of 0.02
 C2H-C3H \\sim C2I-C3I
 with sigma of 0.02
 C3H-C4H \\sim C3I-C4I
 with sigma of 0.02
 O1H-C2H \\sim O1I-C2I
 with sigma of 0.04
 O1H-C3H \\sim O1I-C3I
 with sigma of 0.04
 C2H-C4H \\sim C2I-C4I
 with sigma of 0.04
 C1H-C3H \\sim C1I-C3I
 with sigma of 0.04
 C1H-C4H \\sim C1I-C4I
 with sigma of 0.04
 O1L-C1L \\sim O1M-C1M
 with sigma of 0.02
 O1L-C4L \\sim O1M-C4M
 with sigma of 0.02
 C3L-C4L \\sim C3M-C4M
 with sigma of 0.02
 C3L-C2L \\sim C3M-C2M
 with sigma of 0.02
 C1L-C2L \\sim C1M-C2M
 with sigma of 0.02
 O1L-C3L \\sim O1M-C3M
 with sigma of 0.04
 O1L-C2L \\sim O1M-C2M
 with sigma of 0.04
 C3L-C1L \\sim C3M-C1M
 with sigma of 0.04
 C1L-C4L \\sim C1M-C4M
 with sigma of 0.04
 C4L-C2L \\sim C4M-C2M
 with sigma of 0.04
 C4K-C3J \\sim C4K-C3K
 with sigma of 0.02
 C2K-C3J \\sim C2K-C3K
 with sigma of 0.02
3. Rigid bond restraints
 O1D, O1E, C1D, C2D, C3D, C4D, C1E, C2E, C3E, C4E
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
O1D \\sim O1E \\sim C1D \\sim C2D \\sim C3D \\sim C4D \\sim C1E \\sim C2E \\sim
C3E \\sim C4E \\sim O1F \\sim O1G \\sim C1F \\sim C2F \\sim C3F \\sim C4F \\sim
C1G \\sim C2G \\sim C3G \\sim C4G \\sim O1H \\sim O1I \\sim C1H \\sim C2H \\sim
C3H \\sim C4H \\sim C1I \\sim C2I \\sim C3I \\sim C4I \\sim O1K \\sim C3J \\sim
C1K \\sim C2K \\sim C3K \\sim C4K \\sim O1L \\sim O1M \\sim C1L \\sim C2L \\sim
C3L \\sim C4L \\sim C1M \\sim C2M \\sim C3M \\sim C4M: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(O1E)=Sof(C1E)=Sof(H1EA)=Sof(H1EB)=Sof(C2E)=Sof(H2EA)=Sof(H2EB)=Sof(C3E)=
 Sof(H3EA)=Sof(H3EB)=Sof(C4E)=Sof(H4EA)=Sof(H4EB)=1-FVAR(1)
 Sof(O1D)=Sof(C1D)=Sof(H1DA)=Sof(H1DB)=Sof(C2D)=Sof(H2DA)=Sof(H2DB)=Sof(C3D)=
 Sof(H3DA)=Sof(H3DB)=Sof(C4D)=Sof(H4DA)=Sof(H4DB)=FVAR(1)
 Sof(O1G)=Sof(C1G)=Sof(H1GA)=Sof(H1GB)=Sof(C2G)=Sof(H2GB)=Sof(H2GA)=Sof(C3G)=
 Sof(H3GA)=Sof(H3GB)=Sof(C4G)=Sof(H4GA)=Sof(H4GB)=1-FVAR(2)
 Sof(O1F)=Sof(C1F)=Sof(H1FA)=Sof(H1FB)=Sof(C2F)=Sof(H2FB)=Sof(H2FA)=Sof(C3F)=
 Sof(H3FA)=Sof(H3FB)=Sof(C4F)=Sof(H4FA)=Sof(H4FB)=FVAR(2)
 Sof(O1I)=Sof(C1I)=Sof(H1IA)=Sof(H1IB)=Sof(C2I)=Sof(H2IA)=Sof(H2IB)=Sof(C3I)=
 Sof(H3IA)=Sof(H3IB)=Sof(C4I)=Sof(H4IA)=Sof(H4IB)=1-FVAR(3)
 Sof(O1H)=Sof(C1H)=Sof(H1HA)=Sof(H1HB)=Sof(C2H)=Sof(H2HA)=Sof(H2HB)=Sof(C3H)=
 Sof(H3HA)=Sof(H3HB)=Sof(C4H)=Sof(H4HA)=Sof(H4HB)=FVAR(3)
 Sof(O1M)=Sof(C1M)=Sof(H1MA)=Sof(H1MB)=Sof(C2M)=Sof(H2MB)=Sof(H2MA)=Sof(C3M)=
 Sof(H3MB)=Sof(H3MA)=Sof(C4M)=Sof(H4MB)=Sof(H4MA)=1-FVAR(4)
 Sof(O1L)=Sof(C1L)=Sof(H1LA)=Sof(H1LB)=Sof(C2L)=Sof(H2LB)=Sof(H2LA)=Sof(C3L)=
 Sof(H3LB)=Sof(H3LA)=Sof(C4L)=Sof(H4LB)=Sof(H4LA)=FVAR(4)
 Sof(H2KC)=Sof(H2KD)=Sof(C3K)=Sof(H3KA)=Sof(H3KB)=Sof(H4KC)=Sof(H4KD)=1-FVAR(5)
 Sof(C3J)=Sof(H3JA)=Sof(H3JB)=Sof(H2KA)=Sof(H2KB)=Sof(H4KA)=Sof(H4KB)=FVAR(5)
6.a Secondary CH2 refined with riding coordinates:
 C1D(H1DA,H1DB), C2D(H2DA,H2DB), C3D(H3DA,H3DB), C4D(H4DA,H4DB), C1E(H1EA,
 H1EB), C2E(H2EA,H2EB), C3E(H3EA,H3EB), C4E(H4EA,H4EB), C1F(H1FA,H1FB),
 C2F(H2FB,H2FA), C3F(H3FA,H3FB), C4F(H4FA,H4FB), C1G(H1GA,H1GB), C2G(H2GB,H2GA),
  C3G(H3GA,H3GB), C4G(H4GA,H4GB), C1H(H1HA,H1HB), C2H(H2HA,H2HB), C3H(H3HA,
 H3HB), C4H(H4HA,H4HB), C1I(H1IA,H1IB), C2I(H2IA,H2IB), C3I(H3IA,H3IB),
 C4I(H4IA,H4IB), C3J(H3JA,H3JB), C1K(H1KA,H1KB), C2K(H2KA,H2KB), C2K(H2KC,H2KD),
  C3K(H3KA,H3KB), C4K(H4KA,H4KB), C4K(H4KC,H4KD), C1L(H1LA,H1LB), C2L(H2LB,
 H2LA), C3L(H3LB,H3LA), C4L(H4LB,H4LA), C1M(H1MA,H1MB), C2M(H2MB,H2MA),
 C3M(H3MB,H3MA), C4M(H4MB,H4MA)
6.b Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C2A(H2A), C3A(H3A), C4A(H4A), C6A(H6A), C8A(H8A), C10A(H10A),
 C11A(H11A), C13A(H13A), C15A(H15A), C17A(H17A), C18A(H18A), C22A(H22A),
 C23A(H23A), C24A(H24A), C25A(H25A), C1B(H1B), C2B(H2B), C3B(H3B), C4B(H4B),
 C6B(H6B), C8B(H8B), C10B(H10B), C11B(H11B), C13B(H13B), C15B(H15B), C17B(H17B),
  C18B(H18B), C22B(H22B), C23B(H23B), C24B(H24B), C25B(H25B), C1C(H1C),
 C2C(H2C), C3C(H3C), C4C(H4C), C6C(H6C), C8C(H8C), C10C(H10C), C11C(H11C),
 C13C(H13C), C15C(H15C), C17C(H17C), C18C(H18C), C22C(H22C), C23C(H23C),
 C24C(H24C), C25C(H25C)
;
_shelx_res_checksum              79580
_shelx_hkl_checksum              98611