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_4134347
_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         'C40 H32 N12, C16 H10, 4(F6 P), 4(C2 H3 N)'
_chemical_formula_sum            'C64 H54 F24 N16 P4'
_chemical_formula_weight         1627.11
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                81.307(2)
_cell_angle_beta                 87.8564(18)
_cell_angle_gamma                67.7952(17)
_cell_formula_units_Z            1
_cell_length_a                   10.8605(4)
_cell_length_b                   13.1591(5)
_cell_length_c                   13.4694(5)
_cell_measurement_reflns_used    9804
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.198
_cell_measurement_theta_min      3.320
_cell_volume                     1761.33(12)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'Bruker SAINT'
_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      100.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Quazar optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19971
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        65.193
_diffrn_reflns_theta_max         65.193
_diffrn_reflns_theta_min         3.320
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    2.046
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0607 before and 0.0416 after correction. The Ratio of minimum to maximum transmission is 0.9086. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_description       block
_exptl_crystal_F_000             826
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.650
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     518
_refine_ls_number_reflns         5967
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0644
_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^)+(0.1049P)^2^+2.8853P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1789
_refine_ls_wR_factor_ref         0.1839
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5366
_reflns_number_total             5967
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c01114_si_007.cif
_cod_data_source_block           4_Pyrene
_cod_database_code               4134347
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C32, C31, N8, N8A, C31A, C32A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Others
 Sof(N8A)=Sof(C31A)=Sof(C32A)=Sof(H32D)=Sof(H32E)=Sof(H32F)=1-FVAR(1)
 Sof(N8)=Sof(C31)=Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(H32C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13),
 C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C27(H27),
  C28(H28)
4.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C32A(H32D,H32E,H32F)
;
_smtbx_masks_special_details
;
The solvent masking procedure as implemented in Olex2 was used to remove the
electronic contribution of solvent molecules from the refinement.  As the exact
solvent content is not known, only the atoms used in the refinement model are
reported in the formula here.

Total solvent accessible volume / cell = 77.1 Ang^3^ [4.4%]
Total electron count / cell = 17.9
;
_shelx_res_checksum              45249
_shelx_hkl_checksum              45827
_shelx_fab_checksum              51203
_olex2_date_sample_data_collection 2017-03-20
_olex2_date_sample_submission    2017-03-20
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id cx0958
_olex2_submission_special_instructions 'No special instructions were received'