A regioselectively 1,1′,3,3′-tetrazincated ferrocene complex displaying core and peripheral reactivity
Honeyman, Gordon W.; Armstrong, David R.; Clegg, William; Hevia, Eva; Kennedy, Alan R.; McLellan, Ross; Orr, Samantha A.; Parkinson, John A.; Ramsay, Donna L.; Robertson, Stuart D.; Towie, Stephen; Mulvey, Robert E.; Chemical Science 11 (2020) 6510–6520; doi:10.1039/D0SC01612H

data_1557682
_publ_section_title
;
 A regioselectively 1,1&#x2032;,3,3&#x2032;-tetrazincated ferrocene
 complex displaying core and peripheral reactivity
;
_journal_issue                   25
_journal_name_full               'Chemical Science'
_journal_page_first              6510
_journal_page_last               6520
_journal_paper_doi               10.1039/D0SC01612H
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C48 H94 Fe N6 Na2 Zn2, C7 H8'
_chemical_formula_sum            'C55 H102 Fe N6 Na2 Zn2'
_chemical_formula_weight         1079.99
_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     direct
_audit_creation_date             2019-08-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-17 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                99.482(4)
_cell_angle_beta                 90.798(4)
_cell_angle_gamma                99.459(3)
_cell_formula_units_Z            2
_cell_length_a                   12.9797(5)
_cell_length_b                   15.0261(6)
_cell_length_c                   15.9756(8)
_cell_measurement_reflns_used    10013
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.5020
_cell_measurement_theta_min      2.9707
_cell_volume                     3028.7(2)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean 16.0727
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
  1 omega  -53.00   45.00   1.0000    7.3400
omega____ theta____ kappa____ phi______ frames
    -       19.4192  -37.0000   30.0000 98

  2 omega   36.00   95.00   1.0000    7.3400
omega____ theta____ kappa____ phi______ frames
    -       19.4192  179.0000   60.0000 59

  3 omega   -6.00   86.00   1.0000    7.3400
omega____ theta____ kappa____ phi______ frames
    -       19.4192   37.0000 -150.0000 92

  4 omega  -86.00   -7.00   1.0000    7.3400
omega____ theta____ kappa____ phi______ frames
    -      -20.3567  138.0000  178.0000 79

  5 omega  -82.00  -42.00   1.0000    7.3400
omega____ theta____ kappa____ phi______ frames
    -      -20.3567  131.0000    1.0000 40

  6 omega  -90.00  -40.00   1.0000    7.3400
omega____ theta____ kappa____ phi______ frames
    -      -20.3567  -77.0000   30.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0043110000
_diffrn_orient_matrix_UB_12      -0.0185567000
_diffrn_orient_matrix_UB_13      0.0376495000
_diffrn_orient_matrix_UB_21      0.0044021000
_diffrn_orient_matrix_UB_22      -0.0429039000
_diffrn_orient_matrix_UB_23      -0.0246225000
_diffrn_orient_matrix_UB_31      0.0550984000
_diffrn_orient_matrix_UB_32      0.0131115000
_diffrn_orient_matrix_UB_33      0.0009693000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26552
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         2.981
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_description       plank
_exptl_crystal_F_000             1164
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     699
_refine_ls_number_reflns         14120
_refine_ls_number_restraints     201
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0454P)^2^+1.4426P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1154
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9836
_reflns_number_total             14120
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01612h2.cif
_cod_data_source_block           rmst01
_cod_depositor_comments
;Adding full bibliography for 1557679--1557682.cif.

 Adding full bibliography for 1557679--1557682.cif.
;
_cod_database_code               1557682
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C49-C55 = C55A-C53A
 1.5 with sigma of 0.01
 C14-C13 = C14A-C13A = C33-C32 = C33A-C32A
 1.53 with sigma of 0.01
 C15-N2 = C16-N2 = C14-N2 = C13-N1 = C12-N1 = C11-N1
 1.48 with sigma of 0.01
 C15A-N2A = C16A-N2A = C14A-N2A = C13A-N1A = C12A-N1A = C11A-N1A
 1.48 with sigma of 0.01
 N5-C33 = N5-C34 = N5-C35 = N4-C32 = N4-C31 = N4-C30
 1.48 with sigma of 0.01
 N5-C33A = N5-C34A = N5-C35A = N4-C32A = N4-C31A = N4-C30A
 1.48 with sigma of 0.01
3. Rigid bond restraints
 C49A, C50A, C51A, C52A, C53A, C54A, C55A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C55, C49, C50, C51, C52, C53, C54
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N1, N2, C11, C12, C13, C14, C15, C16
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C49A \\sim C50A \\sim C51A \\sim C52A \\sim C53A \\sim C54A \\sim C55A: within
1.7A with sigma of 0.02 and sigma for terminal atoms of 0.02
C55 \\sim C49 \\sim C50 \\sim C51 \\sim C52 \\sim C53 \\sim C54: within 1.7A
with sigma of 0.02 and sigma for terminal atoms of 0.02
N1 \\sim N2 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16: within
1.7A with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(C54) = Uanis(C53A)
Uanis(C55) = Uanis(C55A)
Uanis(N1) = Uanis(N1A)
Uanis(N2) = Uanis(N2A)
Uanis(C11) = Uanis(C11A)
Uanis(C12) = Uanis(C12A)
Uanis(C13) = Uanis(C13A)
Uanis(C14) = Uanis(C14A)
Uanis(C15) = Uanis(C15A)
Uanis(C16) = Uanis(C16A)
Uanis(C30) = Uanis(C30A)
Uanis(C31) = Uanis(C31A)
Uanis(C32) = Uanis(C32A)
Uanis(C33) = Uanis(C33A)
Uanis(C34) = Uanis(C34A)
Uanis(C35) = Uanis(C35A)
5. Others
 Sof(C49A)=Sof(H49A)=Sof(C50A)=Sof(H50A)=Sof(C51A)=Sof(H51A)=Sof(C52A)=
 Sof(H52A)=Sof(C53A)=Sof(C54A)=Sof(H54A)=Sof(C55A)=Sof(H55D)=Sof(H55E)=
 Sof(H55F)=1-FVAR(1)
 Sof(C55)=Sof(H55A)=Sof(H55B)=Sof(H55C)=Sof(C49)=Sof(C50)=Sof(H50)=Sof(C51)=
 Sof(H51)=Sof(C52)=Sof(H52)=Sof(C53)=Sof(H53)=Sof(C54)=Sof(H54)=FVAR(1)
 Sof(N1A)=Sof(N2A)=Sof(C11A)=Sof(H11D)=Sof(H11E)=Sof(H11F)=Sof(C12A)=Sof(H12D)=
 Sof(H12E)=Sof(H12F)=Sof(C13A)=Sof(H13C)=Sof(H13D)=Sof(C14A)=Sof(H14C)=
 Sof(H14D)=Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=Sof(C16A)=Sof(H16D)=
 Sof(H16E)=Sof(H16F)=1-FVAR(2)
 Sof(N1)=Sof(N2)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(H11C)=Sof(C12)=Sof(H12A)=
 Sof(H12B)=Sof(H12C)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14A)=Sof(H14B)=
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=
 FVAR(2)
 Sof(C30A)=Sof(H30D)=Sof(H30E)=Sof(H30F)=Sof(C31A)=Sof(H31D)=Sof(H31E)=
 Sof(H31F)=Sof(C32A)=Sof(H32C)=Sof(H32D)=Sof(C33A)=Sof(H33C)=Sof(H33D)=
 Sof(C34A)=Sof(H34D)=Sof(H34E)=Sof(H34F)=Sof(C35A)=Sof(H35D)=Sof(H35E)=
 Sof(H35F)=1-FVAR(3)
 Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=
 Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(C34)=Sof(H34A)=
 Sof(H34B)=Sof(H34C)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(H35C)=FVAR(3)
6.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,
 H20B), C32(H32A,H32B), C33(H33A,H33B), C37(H37A,H37B), C38(H38A,H38B),
 C39(H39A,H39B), C32A(H32C,H32D), C33A(H33C,H33D), C13A(H13C,H13D), C14A(H14C,
 H14D)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C50(H50),
 C51(H51), C52(H52), C53(H53), C54(H54), C49A(H49A), C50A(H50A), C51A(H51A),
 C52A(H52A), C54A(H54A)
6.c Fitted hexagon refined as free rotating group:
 C49(C50,C51,C52,C53,C54), C49A(C50A,C51A,C52A,C53A,C54A)
6.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,
 H25B,H25C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C),
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C34(H34A,H34B,H34C), C35(H35A,H35B,
 H35C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C44(H44A,
 H44B,H44C), C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C48(H48A,H48B,H48C),
 C30A(H30D,H30E,H30F), C31A(H31D,H31E,H31F), C34A(H34D,H34E,H34F), C35A(H35D,
 H35E,H35F), C11A(H11D,H11E,H11F), C12A(H12D,H12E,H12F), C15A(H15D,H15E,H15F),
 C16A(H16D,H16E,H16F), C55(H55A,H55B,H55C), C55A(H55D,H55E,H55F)
;
_shelx_res_checksum              87289
_olex2_submission_special_instructions 'No special instructions were received'