Tetrazine metallation boosts rate and regioselectivity of inverse electron demand Diels-Alder (iEDDA) addition of dienophiles.
Schnierle, Marc; Blickle, Svenja; Filippou, Vasileios; Ringenberg, Mark R.; Chemical communications (Cambridge, England) 56 (2020) 12033–12036; doi:10.1039/d0cc03805a

data_7127212
_publ_section_title
;
 Tetrazine metallation boosts rate and regioselectivity of inverse
 electron demand Diels-Alder (iEDDA) addition of dienophiles.
;
_journal_issue                   80
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              12033
_journal_page_last               12036
_journal_paper_doi               10.1039/d0cc03805a
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C22 H17 Cl Fe N3 O3 Re'
_chemical_formula_sum            'C22 H17 Cl Fe N3 O3 Re'
_chemical_formula_weight         648.90
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     direct
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;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-21 deposited with the CCDC.	2020-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.9810(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9074(3)
_cell_length_b                   12.0184(3)
_cell_length_c                   14.9765(4)
_cell_measurement_reflns_used    58206
_cell_measurement_temperature    135.02
_cell_measurement_theta_max      33.17
_cell_measurement_theta_min      1.73
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      135.02
_diffrn_measured_fraction_theta_full 0.9991
_diffrn_measured_fraction_theta_max 0.9991
_diffrn_measurement_device_type  'Apex II, Brucker'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            58206
_diffrn_reflns_theta_full        33.1750
_diffrn_reflns_theta_max         33.17
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    6.537
_exptl_absorpt_correction_T_max  0.8095
_exptl_absorpt_correction_T_min  0.3323
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
'J. de Meulenaar and H. Tompa, Acta Crystallogr., Sect A 1965, 19, 1014-1018'
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.0303
_exptl_crystal_description       plank
_exptl_crystal_F_000             1247.1337
_exptl_crystal_preparation       'see manuscript'
_exptl_crystal_recrystallization_method 'see manuscript'
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_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.8257
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_parameters     280
_refine_ls_number_reflns         8110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9942
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0197
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0163P)^2^+1.0544P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0374
_refine_ls_wR_factor_ref         0.0415
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              -19
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                6575
_reflns_number_total             8110
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d0cc03805a2.cif
_cod_data_source_block           ac479a
_cod_depositor_comments
'Adding full bibliography for 7127209--7127213.cif.'
_cod_database_code               7127212
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C22(H22), C21(H21),
 C20(H20), C19(H19), C4(H4), C7(H7), C6(H6), C5(H5), C12(H12)
;
_olex2_exptl_crystal_mounting_method cyroloop
_olex2_submission_special_instructions 'No special instructions were received'