Synthesis, Characterization, and Cycloaddition Reactivity of a Monocyclic Aromatic 1,2,3,5-Tetrazine.
Wu, Zhi-Chen; Boger, Dale L.; Journal of the American Chemical Society 141 (2019) 16388–16397; doi:10.1021/jacs.9b07744

data_4127689
_publ_section_title
;
 Synthesis, Characterization, and Cycloaddition Reactivity of a Monocyclic
 Aromatic 1,2,3,5-Tetrazine.
;
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16388
_journal_page_last               16397
_journal_paper_doi               10.1021/jacs.9b07744
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         '2(C26 H16 N8 O8), C1 H1 Cl3'
_chemical_formula_sum            'C53 H33 Cl3 N16 O16'
_chemical_formula_weight         1256.30
_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_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-10-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 115.2070(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2215(4)
_cell_length_b                   31.0295(7)
_cell_length_c                   14.5700(4)
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.39
_cell_measurement_theta_min      2.18
_cell_volume                     5408.2(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            59891
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         1.312
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  0.4903
_exptl_absorpt_correction_T_min  0.4553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0823 before and 0.0474 after correction. The Ratio of minimum to maximum transmission is 0.9286. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_description       block
_exptl_crystal_F_000             2568
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.125
_refine_diff_density_max         1.110
_refine_diff_density_min         -0.999
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     806
_refine_ls_number_reflns         9895
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0496
_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^)+(0.0540P)^2^+7.4841P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1285
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7615
_reflns_number_total             9895
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b07744_si_003.cif
_cod_data_source_block           boger92
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4127689
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.962
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 Cl2A-C1A \\sim Cl2B-C1B
 with sigma of 0.02
 Cl1A-C1A \\sim Cl1B-C1B
 with sigma of 0.02
 Cl3A-C1A \\sim Cl3B-C1B
 with sigma of 0.02
 Cl2A-Cl1A \\sim Cl2B-Cl1B
 with sigma of 0.04
 Cl2A-Cl3A \\sim Cl2B-Cl3B
 with sigma of 0.04
 Cl1A-Cl3A \\sim Cl1B-Cl3B
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C1B) = Uanis(C1A)
Uanis(Cl1B) = Uanis(Cl1A)
Uanis(Cl2A) = Uanis(Cl2B)
Uanis(Cl3A) = Uanis(Cl3B)
4. Others
 Sof(Cl1B)=Sof(Cl2B)=Sof(Cl3B)=Sof(C1B)=Sof(H1B)=1-FVAR(1)
 Sof(Cl1A)=Sof(Cl2A)=Sof(Cl3A)=Sof(C1A)=Sof(H1A)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C1A(H1A), C1B(H1B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C16(H16), C17(H17), C19(H19), C20(H20), C23(H23), C25(H25),
  C4'(H4'), C5'(H5'), C6'(H6'), C7'(H7'), C8'(H8'), C10'(H10'), C11'(H11'),
 C12'(H12'), C13'(H13'), C14'(H14'), C16'(H16'), C17'(H17'), C19'(H19'),
 C20'(H20'), C23'(H23'), C25'(H25')
;
_shelx_res_checksum              98012
_shelx_hkl_checksum              72902
_olex2_submission_special_instructions 'No special instructions were received'