Five-component, one-pot synthesis of an electroactive rotaxane comprising a bisferrocene macrocycle
Lagesse, Natalie; Pisciottani, Luca; Douarre, Maxime; Godard, Pascale; Kauffmann, Brice; Martí-Centelles, Vicente; McClenaghan, Nathan D.; Beilstein Journal of Organic Chemistry 16 (2020) 1564–1571; doi:10.3762/bjoc.16.128

data_4038541
_publ_section_title
;
 Five-component, one-pot synthesis of an electroactive rotaxane comprising
 a bisferrocene macrocycle
;
_journal_name_full               'Beilstein Journal of Organic Chemistry'
_journal_page_first              1564
_journal_page_last               1571
_journal_paper_doi               10.3762/bjoc.16.128
_journal_volume                  16
_journal_year                    2020
_chemical_formula_moiety         'C26 H22 Fe N2 O2, C10 H20 N O'
_chemical_formula_sum            'C36 H42 Fe N3 O3'
_chemical_formula_weight         620.57
_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_date             2019-11-27
_audit_creation_method
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                99.002(5)
_cell_angle_beta                 108.001(5)
_cell_angle_gamma                90.007(4)
_cell_formula_units_Z            2
_cell_length_a                   9.5366(5)
_cell_length_b                   11.6279(7)
_cell_length_c                   14.9396(9)
_cell_measurement_reflns_used    5634
_cell_measurement_temperature    120
_cell_measurement_theta_max      55.5360
_cell_measurement_theta_min      4.8930
_cell_volume                     1554.09(16)
_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 (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      120
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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   -156.00  24.00   1.00   15.00    --  -66.00  48.00  36.00  180
  2  \w    -87.00  78.00   1.00    2.00    --    3.00  48.00 -36.00  165
  3  \w   -156.00  24.00   1.00   15.00    --  -66.00  60.00-180.00  180
  4  \w   -156.00  24.00   1.00   15.00    --  -66.00  60.00 108.00  180
  5  \w   -156.00  24.00   1.00   15.00    --  -66.00  60.00 -36.00  180
  6  \w   -128.00   7.00   1.00   15.00    --  -66.00  48.00-108.00  135
  7  \w   -156.00  24.00   1.00   15.00    --  -66.00  12.00-180.00  180
  8  \w   -155.00 -68.00   1.00   15.00    --  -66.00  60.00-108.00   87
  9  \w   -147.00 -92.00   1.00   15.00    --  -66.00  60.00 144.00   55
 10  \w   -156.00-111.00   1.00   15.00    --  -66.00  60.00  36.00   45
 11  \w    -34.00  11.00   1.00    2.00    --    3.00  36.00-180.00   45
 12  \w    -75.00   2.00   1.00   15.00    --  -66.00  12.00 -72.00   77
 13  \w   -156.00  24.00   1.00   15.00    --  -66.00  48.00 108.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1681817000
_diffrn_orient_matrix_UB_12      0.0186288000
_diffrn_orient_matrix_UB_13      0.0229720000
_diffrn_orient_matrix_UB_21      -0.0253080000
_diffrn_orient_matrix_UB_22      0.0821089000
_diffrn_orient_matrix_UB_23      -0.0744208000
_diffrn_orient_matrix_UB_31      0.0012119000
_diffrn_orient_matrix_UB_32      0.1046523000
_diffrn_orient_matrix_UB_33      0.0775628000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14633
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        55.679
_diffrn_reflns_theta_max         55.679
_diffrn_reflns_theta_min         4.562
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.208
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64483
_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
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       needle
_exptl_crystal_F_000             658
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0011(3)
_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   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         3928
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0717P)^2^+0.4525P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1180
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3378
_reflns_number_total             3928
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1860-5397-16-128-S2.cif
_cod_data_source_block           lpb_917_test
_cod_depositor_comments          'Adding full bibliography for 4038541.cif.'
_cod_database_code               4038541
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C30 H30 N4 O6 Fe'
_reflns_odcompleteness_completeness 98.10
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     55.61
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00E(H00C,H00D), C00F(H00E,H00F), C00R(H00A,H00B), C00T(H00H,H00J), C00V(H00N,
 H00R), C00W(H00S,H00T), C013(H01C,H01D), C014(H01A,H01B), C015(H01E,H01F)
2.b Aromatic/amide H refined with riding coordinates:
 N005(H005), N007(H007), C008(H008), C00G(H00G), C00I(H00I), C00K(H00K),
 C00L(H00L), C00M(H00M), C00O(H00O), C00P(H00P), C00Q(H00Q), C00U(H00U),
 C00X(H00X), C00Y(H00Y), C010(H010), C011(H011), C012(H012), C016(H016)
2.c Idealised Me refined as rotating group:
 C00Z(H00V,H00W,H00Z), C017(H01G,H01H,H01I)
;
_shelx_res_checksum              35478
_shelx_hkl_checksum              38967
_olex2_submission_original_sample_id lpb_917
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.645
_oxdiff_exptl_absorpt_empirical_full_min 0.277