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_7127213
_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         'C18 H13 Cl N3 O3 Re'
_chemical_formula_sum            'C18 H13 Cl N3 O3 Re'
_chemical_formula_weight         540.981
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-03-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.01.31 svn.r88ba2a32 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-03-21 deposited with the CCDC.	2020-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.870(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0781(7)
_cell_length_b                   10.9568(10)
_cell_length_c                   22.080(2)
_cell_measurement_reflns_used    22000
_cell_measurement_temperature    135.0
_cell_measurement_theta_max      27
_cell_measurement_theta_min      1.7
_cell_volume                     2193.5(3)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      135.0
_diffrn_measured_fraction_theta_full 0.9962
_diffrn_measured_fraction_theta_max 0.9958
_diffrn_measurement_device_type  'Brucker Apex II'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_Laue_measured_fraction_full 0.9962
_diffrn_reflns_Laue_measured_fraction_max 0.9958
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            22804
_diffrn_reflns_point_group_measured_fraction_full 0.9962
_diffrn_reflns_point_group_measured_fraction_max 0.9958
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    5.681
_exptl_absorpt_correction_T_max  0.6576
_exptl_absorpt_correction_T_min  0.5411
_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_density_diffrn    1.638
_exptl_crystal_description       'red-brown prisms'
_exptl_crystal_F_000             1030.636
_exptl_crystal_preparation       'See Manuscript'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2/n-hexanes'
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.085
_refine_diff_density_max         2.2243
_refine_diff_density_min         -1.7079
_refine_diff_density_rms         0.3393
_refine_ls_d_res_high            0.7492
_refine_ls_d_res_low             11.0261
_refine_ls_goodness_of_fit_ref   0.9574
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     211
_refine_ls_number_reflns         5438
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      0.9541
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0301P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0785
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              29
_reflns_limit_l_min              -10
_reflns_number_gt                3970
_reflns_number_total             5438
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d0cc03805a2.cif
_cod_data_source_block           ac484
_cod_depositor_comments
'Adding full bibliography for 7127209--7127213.cif.'
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7127213
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N1) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C10(H10)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C18(H18), C17(H17), C16(H16), C15(H15), C14(H14), C4(H4),
 C5(H5), C6(H6), C7(H7), N3(H3)
3.c Fitted hexagon refined as free rotating group:
 C13(C18,C17,C16,C15,C14), N1(C4,C5,C6,C7,C8)
;
_olex2_exptl_crystal_mounting_method 'cyroloop '
_olex2_submission_special_instructions 'No special instructions were received'