TetrazineBox: A Structurally Transformative ToolBox.
Guo, Qing-Hui; Zhou, Jiawang; Mao, Haochuan; Qiu, Yunyan; Nguyen, Minh T.; Feng, Yuanning; Liang, Jiaqi; Shen, Dengke; Li, Penghao; Liu, Zhichang; Wasielewski, Michael R.; Stoddart, J. Fraser; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c01114

data_4134339
_publ_section_title
;
 TetrazineBox: A Structurally Transformative ToolBox.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c01114
_journal_year                    2020
_chemical_formula_moiety         '2(F6 P), C20 H18 N6, 3(C2 H3 N)'
_chemical_formula_sum            'C26 H27 F12 N9 P2'
_chemical_formula_weight         755.50
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-21
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                104.290(2)
_cell_angle_beta                 94.193(2)
_cell_angle_gamma                112.848(2)
_cell_formula_units_Z            2
_cell_length_a                   10.3447(4)
_cell_length_b                   11.4860(4)
_cell_length_c                   17.3882(6)
_cell_measurement_reflns_used    9860
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.26
_cell_volume                     1811.71(12)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33754
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.61
_diffrn_reflns_theta_min         2.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1293 before and 0.0377 after correction.
The Ratio of minimum to maximum transmission is 0.9195.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.292
_exptl_crystal_size_mid          0.222
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.744
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         8239
_refine_ls_number_restraints     173
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0516
_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^)+(0.0655P)^2^+1.8015P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1422
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6923
_reflns_number_total             8239
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c01114_si_003.cif
_cod_data_source_block           5PF6
_cod_database_code               4134339
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 P1AA-F3AA
 1.6 with sigma of 0.02
 P1AA-F8
 1.6 with sigma of 0.02
 P1AA-F4
 1.6 with sigma of 0.02
 P1AA-F2AA
 1.6 with sigma of 0.02
 P1AA-F0AA
 1.6 with sigma of 0.02
 P1AA-F9
 1.6 with sigma of 0.02
 C10-N017 \\sim C01B-N017
 with sigma of 0.02
 F9-F8 \\sim F2AA-F3AA
 with sigma of 0.02
3. Restrained planarity
 F9, P1AA, F2AA, F4
 with sigma of 0.1
 F3AA, F8, F4, P1AA
 with sigma of 0.1
 F2AA, F3AA, F9, F8, P1AA
 with sigma of 0.1
4. Rigid bond restraints
 C10, C01B, C2, C5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F2AA, P1AA, F9, F0AA, F3AA, F8, F4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
C01B \\sim C10 \\sim C5 \\sim C2: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
F2AA \\sim P1AA \\sim F9 \\sim F0AA \\sim F3AA \\sim F8 \\sim F4: within 2A
with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(C10) \\sim Ueq, Uanis(C01B) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C5)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F2AA) \\sim Ueq, Uanis(P1AA) \\sim Ueq, Uanis(F9) \\sim Ueq, Uanis(F0AA)
\\sim Ueq, Uanis(F3AA) \\sim Ueq, Uanis(F8) \\sim Ueq, Uanis(F4) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
6. Others
 Fixed Sof: P002(0.9) F009(0.9) F00G(0.9) F00H(0.9) F00I(0.9) F00J(0.9)
 F00P(0.9) C01B(0.5) C2(0.5) H2A(0.5) H2B(0.5) H2C(0.5) C5(0.5) H5A(0.5)
 H5B(0.5) H5C(0.5) C10(0.5) P1AA(0.1) F2AA(0.1) F4(0.1) F3AA(0.1) F8(0.1)
 F9(0.1) F0AA(0.1)
7.a Riding coordinates:
 N00E(H00E), N00F(H00F)
7.b Secondary CH2 refined with riding coordinates:
 C00Y(H00A,H00B), C011(H01A,H01B)
7.c Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00X(H00X),
 C00Z(H00Z), C010(H010), C012(H012), C013(H013), C014(H014), C015(H015)
7.d Idealised Me refined as rotating group:
 C019(H01C,H01D,H01E), C01C(H01F,H01G,H01H), C2(H2A,H2B,H2C), C5(H5A,H5B,H5C)
;
_shelx_res_checksum              49445
_shelx_hkl_checksum              73132
_shelx_fab_checksum              3628
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'