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_7127211
_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 H19 Cl N3 O3 Re'
_chemical_formula_sum            'C18 H19 Cl N3 O3 Re'
_chemical_formula_weight         547.01
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-06-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-09 deposited with the CCDC.	2020-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.284(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.9274(18)
_cell_length_b                   12.2202(9)
_cell_length_c                   17.9025(19)
_cell_measurement_reflns_used    24957
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.2
_cell_measurement_theta_min      2.2
_cell_volume                     3817.1(6)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'Apex II, Brucker'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2298
_diffrn_reflns_av_unetI/netI     0.3791
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24957
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.919
_diffrn_reflns_theta_min         2.035
_exptl_absorpt_coefficient_mu    6.529
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark brown'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.904
_exptl_crystal_description       needle
_exptl_crystal_F_000             2112
_exptl_crystal_preparation       'see manuscript'
_exptl_crystal_recrystallization_method 'see manuscript'
_refine_diff_density_max         3.834
_refine_diff_density_min         -1.598
_refine_diff_density_rms         0.318
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         6069
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      0.948
_refine_ls_R_factor_all          0.1927
_refine_ls_R_factor_gt           0.0675
_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^)+(0.0629P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1503
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2964
_reflns_number_total             6069
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc03805a2.cif
_cod_data_source_block           stams02
_cod_depositor_comments
;
Adding full bibliography for 7127209--7127213.cif.

2025-03-31
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C36 H38 Cl2 N6 O6 Re2'
_cod_original_formula_weight         1094.02
_cod_original_formula_moiety         '2(C18 H19 Cl N3 O3 Re)'
_cod_original_formula_units_Z            4
_cod_database_code               7127211
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C16) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C11) \\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 Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,
 H15B), C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C18(H18), N3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'