Intramolecular tetrazine-acryloyl cycloaddition: chemistry and applications
Hamsath, Akil; Lederberg, Oren L.; Cui, Qi; Shieh, Meg; Lam, Yannie; Brummett, Brock J.; Xu, Shi; Robinson, Jerome R.; Xian, Ming; Chemical Science  (2022) –; doi:10.1039/D2SC04331A

data_1567502
_publ_section_title
;
 Intramolecular tetrazine-acryloyl cycloaddition: chemistry and
 applications
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC04331A
_journal_year                    2022
_chemical_formula_moiety         '2(C16 H11 N3 O2)'
_chemical_formula_sum            'C32 H22 N6 O4'
_chemical_formula_weight         554.55
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-07-27 deposited with the CCDC.	2022-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.4300(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0961(4)
_cell_length_b                   9.9627(3)
_cell_length_c                   22.3275(6)
_cell_measurement_reflns_used    9853
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.49
_cell_volume                     2460.87(13)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            62503
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.552
_diffrn_reflns_theta_min         2.240
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0532 before and 0.0495 after correction.
The Ratio of minimum to maximum transmission is 0.9588.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0387
_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^)+(0.0512P)^2^+1.0574P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5025
_reflns_number_total             5678
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04331a3.cif
_cod_data_source_block           mx20220725_0m
_cod_database_code               1567502
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.984
_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.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16), N4(H4), C21(H21), C22(H22), C23(H23), C24(H24), C29(H29), C30(H30),
 C31(H31), C32(H32)
;
_shelx_res_checksum              15958
_shelx_hkl_checksum              51254
_olex2_submission_special_instructions 'No special instructions were received'