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_7127209
_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         'C10 H5 Cl N5 O3 Re, C0.5 H Cl'
_chemical_formula_sum            'C10.5 H6 Cl2 N5 O3 Re'
_chemical_formula_weight         507.308
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_Int_Tables_number      15
_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                 99.720(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.0600(8)
_cell_length_b                   13.0072(8)
_cell_length_c                   13.9753(7)
_cell_measurement_reflns_used    17080
_cell_measurement_temperature    135.01
_cell_measurement_theta_max      66
_cell_measurement_theta_min      5.16
_cell_volume                     2877.5(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      135.01
_diffrn_measured_fraction_theta_full 0.9515
_diffrn_measured_fraction_theta_max 0.9515
_diffrn_measurement_device_type  'Brucker Apex II'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.9515
_diffrn_reflns_Laue_measured_fraction_max 0.9515
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17080
_diffrn_reflns_point_group_measured_fraction_full 0.9515
_diffrn_reflns_point_group_measured_fraction_max 0.9515
_diffrn_reflns_theta_full        66.3264
_diffrn_reflns_theta_max         66.33
_diffrn_reflns_theta_min         5.16
_exptl_absorpt_coefficient_mu    20.131
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'R.H. Blessing, Acta Crystallogr., Sect A 1995, 51, 33-38'
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.342
_exptl_crystal_description       plate
_exptl_crystal_F_000             1869.829
_exptl_crystal_preparation       'See manuscript'
_exptl_crystal_recrystallization_method 'Slow evaporation of CH2Cl2'
_exptl_crystal_size_max          0.146
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.029
_refine_diff_density_max         6.2654
_refine_diff_density_min         -2.5716
_refine_diff_density_rms         0.4075
_refine_ls_d_res_high            0.8417
_refine_ls_d_res_low             8.5676
_refine_ls_goodness_of_fit_ref   1.0465
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    13
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2412
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0465
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0750
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1839P)^2^+6.2117P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1901
_refine_ls_wR_factor_ref         0.2250
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              -18
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                1954
_reflns_number_total             2412
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d0cc03805a2.cif
_cod_data_source_block           ac488
_cod_depositor_comments
'Adding full bibliography for 7127209--7127213.cif.'
_cod_database_code               7127209
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: H11a(0.5) H11b(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C4(H4), C5(H5), C10(H10)
;
_olex2_exptl_crystal_mounting_method cryroloop
_olex2_submission_special_instructions 'No special instructions were received'