Towards triptycene functionalization and triptycene-linked porphyrin arrays.
Locke, Gemma M.; Flanagan, Keith J.; Senge, Mathias O.; Beilstein journal of organic chemistry 16 (2020) 763–777; doi:10.3762/bjoc.16.70

data_4038273
_publ_section_title
;
 Towards triptycene functionalization and triptycene-linked porphyrin
 arrays.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              763
_journal_page_last               777
_journal_paper_doi               10.3762/bjoc.16.70
_journal_volume                  16
_journal_year                    2020
_chemical_formula_moiety         'C100 H90 N8 Ni Zn'
_chemical_formula_sum            'C100 H90 N8 Ni Zn'
_chemical_formula_weight         1527.87
_chemical_name_systematic
'9-((10,20-dihexyl-15-phenylporphyrinato-5-yl)ethynyl)zinc(II)-10-((10,20-dihexyl-15-phenylporphyrinato-5-yl)ethynyl) nickel(II) triptycene'
_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             2019-07-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90.007(2)
_cell_angle_beta                 94.017(2)
_cell_angle_gamma                90.367(2)
_cell_formula_units_Z            2
_cell_length_a                   10.5794(9)
_cell_length_b                   12.0811(10)
_cell_length_c                   31.213(3)
_cell_measurement_reflns_used    9463
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      2.55
_cell_volume                     3979.5(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX 3 (Bruker, 2016) '
_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(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_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       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            85838
_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         25.250
_diffrn_reflns_theta_min         0.654
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              graphite-monochromated
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.593
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0597 before and 0.0469 after correction. The Ratio of minimum to maximum transmission is 0.8905. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1608
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.984
_refine_diff_density_min         -0.937
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     891
_refine_ls_number_reflns         14446
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0695
_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^)+(0.0599P)^2^+13.2408P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1631
_refine_ls_wR_factor_ref         0.1797
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11116
_reflns_number_total             14446
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1860-5397-16-70-S3.cif
_cod_data_source_block           kjf275
_cod_depositor_comments
'Adding full bibliography for 4038273--4038274.cif.'
_cod_original_cell_volume        3979.4(6)
_cod_database_code               4038273
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.842
_shelx_estimated_absorpt_t_min   0.842
_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. Restrained distances
 C9B-C10B = C20_1-C201_1 = C202_1-C201_1 = C11B-C10B = C12B-C11B = C202_1-
 C203_1 = C13B-C12B = C204_1-C203_1 = C205_1-C204_1 = C14B-C13B = C205_1-C206_1
 = C15B-C14B
 1.52 with sigma of 0.01
 C3_1-C4_1 = C4_1-C18B
 1.42 with sigma of 0.01
 C20_2-C201_2 = C21B-C22B = C23B-C22B = C202_2-C201_2 = C203_2-C202_2 = C23B-
 C24B = C24B-C25B = C204_2-C203_2 = C204_2-C205_2 = C26B-C25B = C206_2-C205_2 =
 C26B-C27B
 1.52 with sigma of 0.01
 C1B-C15_1 \\sim C151_1-C15_1
 with sigma of 0.02
 C31B-C15_2 \\sim C151_2-C15_2
 with sigma of 0
3. Uiso/Uaniso restraints and constraints
Uanis(C26B) \\sim Ueq, Uanis(C204_2) \\sim Ueq: with sigma of 0.001 and sigma
for terminal atoms of 0.002
Uanis(C3_1) = Uanis(C18B)
Uanis(C15B) = Uanis(C206_1) = Uanis(C14B) = Uanis(C205_1) = Uanis(C204_1) =
Uanis(C13B) = Uanis(C203_1) = Uanis(C12B) = Uanis(C11B) = Uanis(C202_1) =
Uanis(C201_1) = Uanis(C10B)
Uanis(C2_1) = Uanis(C17B) = Uanis(C16B) = Uanis(C1_1) = Uanis(C9B) =
Uanis(C20_1) = Uanis(C19_1) = Uanis(C8B) = Uanis(C7B) = Uanis(C18_1)
Uanis(C1B) = Uanis(C151_1) = Uanis(C2B) = Uanis(C156_1) = Uanis(C3B) =
Uanis(C155_1) = Uanis(C4B) = Uanis(C154_1) = Uanis(C5B) = Uanis(C153_1) =
Uanis(C6B) = Uanis(C152_1)
Uanis(C30B) = Uanis(C17_2)
Uanis(C201_2) = Uanis(C22B) = Uanis(C202_2) = Uanis(C23B) = Uanis(C203_2) =
Uanis(C24B) = Uanis(C204_2) = Uanis(C25B) = Uanis(C26B) = Uanis(C206_2) =
Uanis(C27B) = Uanis(C205_2)
Uanis(C151_2) = Uanis(C31B) = Uanis(C32B) = Uanis(C156_2) = Uanis(C33B) =
Uanis(C155_2) = Uanis(C34B) = Uanis(C154_2) = Uanis(C35B) = Uanis(C153_2) =
Uanis(C36B) = Uanis(C152_2)
Uanis(C18_2) = Uanis(C29B) = Uanis(C19_2) = Uanis(C28B) = Uanis(C20_2) =
Uanis(C21B) = Uanis(C1_2) = Uanis(C20B) = Uanis(C2_2) = Uanis(C19B)
4. Others
 Sof(C18B)=Sof(H18B)=1-FVAR(1)
 Sof(C3)=Sof(H3)=FVAR(1)
 Sof(C17)=1-FVAR(2)
 Sof(C30B)=FVAR(2)
 Fixed Sof: C2B(0.44) H2B(0.44) C1B(0.44) C6B(0.44) H6B(0.44) C5B(0.44)
 H5B(0.44) C4B(0.44) H4B(0.44) C3B(0.44) H3B(0.44) C22B(0.5) H22A(0.5)
 H22B(0.5) C24B(0.5) H24A(0.5) H24B(0.5) C27B(0.5) H27A(0.5) H27B(0.5)
 H27C(0.5) C23B(0.5) H23A(0.5) H23B(0.5) C26B(0.5) H26A(0.5) H26B(0.5)
 C21B(0.5) H30B(0.5) C28B(0.5) C29B(0.5) H29B(0.5) C20B(0.5) C8B(0.5) C10B(0.5)
 H10A(0.5) H10B(0.5) C16B(0.5) C17B(0.5) H17B(0.5) C9B(0.5) C19B(0.5) H19B(0.5)
 C13B(0.5) H13A(0.5) H13B(0.5) C7B(0.5) H7B(0.5) C14B(0.5) H14A(0.5) H14B(0.5)
 C25B(0.5) H25A(0.5) H25B(0.5) C15B(0.5) H15A(0.5) H15B(0.5) H15C(0.5)
 C32B(0.56) H32B(0.56) C33B(0.56) H33B(0.56) C34B(0.56) H34B(0.56) C35B(0.56)
 H35B(0.56) C36B(0.56) H36B(0.56) C31B(0.56) C11B(0.5) H11A(0.5) H11B(0.5)
 C12B(0.5) H12A(0.5) H12B(0.5) C1(0.5) C2(0.5) H2(0.5) H17A(0.5) H17(0.5)
 C18(0.5) H18(0.5) C19(0.5) C20(0.5) C156(0.56) H156(0.56) C151(0.56)
 C152(0.56) H152(0.56) C153(0.56) H153(0.56) C154(0.56) H154(0.56) C155(0.56)
 H155(0.56) C201(0.5) H20A(0.5) H20B(0.5) C202(0.5) H20C(0.5) H20D(0.5)
 C203(0.5) H20E(0.5) H20F(0.5) C204(0.5) H20G(0.5) H20H(0.5) C205(0.5)
 H20I(0.5) H20J(0.5) C206(0.5) H20K(0.5) H20L(0.5) H20M(0.5) C1(0.5) C2(0.5)
 H2(0.5) H3A(0.5) H3B(0.5) H17(0.5) C18(0.5) H18(0.5) C19(0.5) C20(0.5)
 C156(0.44) H156(0.44) C155(0.44) H155(0.44) C154(0.44) H154(0.44) C153(0.44)
 H153(0.44) C152(0.44) H152(0.44) C151(0.44) C201(0.5) H20A(0.5) H20B(0.5)
 C202(0.5) H20C(0.5) H20D(0.5) C203(0.5) H20E(0.5) H20F(0.5) C204(0.5)
 H20G(0.5) H20H(0.5) C205(0.5) H20I(0.5) H20J(0.5) C206(0.5) H20K(0.5)
 H20L(0.5) H20M(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C22B(H22A,H22B), C24B(H24A,H24B), C23B(H23A,H23B), C26B(H26A,H26B), C10B(H10A,
 H10B), C13B(H13A,H13B), C14B(H14A,H14B), C25B(H25A,H25B), C11B(H11A,H11B),
 C12B(H12A,H12B), C101(H10A,H10B), C102(H10C,H10D), C103(H10E,H10F), C104(H10G,
 H10H), C105(H10I,H10J), C201(H20A,H20B), C202(H20C,H20D), C203(H20E,H20F),
 C204(H20G,H20H), C205(H20I,H20J), C101(H10A,H10B), C102(H10C,H10D), C103(H10E,
 H10F), C104(H10G,H10H), C105(H10I,H10J), C201(H20A,H20B), C202(H20C,H20D),
 C203(H20E,H20F), C204(H20G,H20H), C205(H20I,H20J)
5.b Aromatic/amide H refined with riding coordinates:
 C18B(H18B), C2B(H2B), C6B(H6B), C5B(H5B), C4B(H4B), C3B(H3B), C1'(H1'),
 C4'(H4'), C12'(H12'), C5'(H5'), C15'(H15'), C8'(H8'), C7'(H7'), C2'(H2'),
 C3'(H3'), C6'(H6'), C14'(H14'), C13'(H13'), C30B(H30B), C29B(H29B), C17B(H17B),
  C19B(H19B), C7B(H7B), C32B(H32B), C33B(H33B), C34B(H34B), C35B(H35B),
 C36B(H36B), C2(H2), C3(H3), C7(H7), C8(H8), C12(H12), C13(H13), C17(H17A),
 C17(H17), C18(H18), C156(H156), C152(H152), C153(H153), C154(H154), C155(H155),
  C2(H2), C3(H3A), C3(H3B), C7(H7), C8(H8), C12(H12), C13(H13), C17(H17),
 C18(H18), C156(H156), C155(H155), C154(H154), C153(H153), C152(H152)
5.c Fitted hexagon refined as free rotating group:
 C2B(C1B,C6B,C5B,C4B,C3B), C32B(C33B,C34B,C35B,C36B,C31B), C156(C151,C152,C153,
 C154,C155), C156(C155,C154,C153,C152,C151)
5.d Idealised Me refined as rotating group:
 C27B(H27A,H27B,H27C), C15B(H15A,H15B,H15C), C106(H10K,H10L,H10M), C206(H20K,
 H20L,H20M), C106(H10K,H10L,H10M), C206(H20K,H20L,H20M)
;
_shelx_res_checksum              76347
_shelx_hkl_checksum              6781
_shelx_fab_checksum              15368
_olex2_submission_special_instructions 'No special instructions were received'