Regiocontrolled Dimerization of Asymmetric Diazaheptacene Derivatives Toward X-shaped Porous Semiconductors
Zhang , Guowei; Zhang, Lei; Lv, Aifeng; Yang, Xingzhou; Zheng, Yonghao; Gu, Wen; Xue, Ning; Chemical Science  (2020) –; doi:10.1039/D0SC03744C

data_1559103
_publ_section_title
;
 Regiocontrolled Dimerization of Asymmetric Diazaheptacene Derivatives
 Toward X-shaped Porous Semiconductors
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC03744C
_journal_year                    2020
_chemical_formula_moiety         'C70 H88 N4 O4 Si2, 0.5(C7 H8)'
_chemical_formula_sum            'C73.5 H92 N4 O4 Si2'
_chemical_formula_weight         1151.69
_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             2018-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-29 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                96.811(3)
_cell_angle_beta                 101.236(3)
_cell_angle_gamma                108.670(3)
_cell_formula_units_Z            2
_cell_length_a                   12.4231(4)
_cell_length_b                   13.9327(5)
_cell_length_c                   21.1782(7)
_cell_measurement_reflns_used    14038
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.5150
_cell_measurement_theta_min      2.0550
_cell_volume                     3341.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      223.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            43305
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         1.573
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.9d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_description       plate
_exptl_crystal_F_000             1242
_exptl_crystal_size_max          0.463
_exptl_crystal_size_mid          0.439
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.997
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     918
_refine_ls_number_reflns         15290
_refine_ls_number_restraints     489
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.0818
_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^)+(0.1060P)^2^+2.8384P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2200
_refine_ls_wR_factor_ref         0.2446
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9982
_reflns_number_total             15290
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc03744c2.cif
_cod_data_source_block           mx7432b
_cod_original_formula_sum        'C73.50 H92 N4 O4 Si2'
_cod_database_code               1559103
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.954
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C76-C71 = C76-C75 = C75-C74 = C74-C73 = C73-C72 = C72-C71
 1.39 with sigma of 0.01
 C77-C71
 1.51 with sigma of 0.01
 C27A-C26 = C27-C26 = C28-C27 = C28A-C27A = C29-C28 = C29A-C28A = C30-C29 =
 C30A-C29A
 1.54 with sigma of 0.01
 C56A-C54A = C55A-C54A = C55-C54 = C56-C54 = C52A-C51A = C52-C51 = C53-C51 =
 C53A-C51A
 1.54 with sigma of 0.01
 Si1-C51A = Si1-C51 = Si1-C54A = Si1-C54
 1.88 with sigma of 0.01
 C64A-C62 = C63-C62 = C63A-C62 = C64-C62
 1.54 with sigma of 0.01
 C30-C28
 2.5 with sigma of 0.02
3. Rigid bond restraints
 C19, C20
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C77 \\sim C71 \\sim C72 \\sim C76 \\sim C73 \\sim C75 \\sim C74: within 1.7A
with sigma of 0.02 and sigma for terminal atoms of 0.04
C27 \\sim C28 \\sim C29 \\sim C30 \\sim C27A \\sim C28A \\sim C29A \\sim C30A:
within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
C51 \\sim C52 \\sim C53 \\sim C51A \\sim C53A \\sim C52A: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04
C54 \\sim C55 \\sim C56 \\sim C54A \\sim C55A \\sim C56A: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04
C62 \\sim C63A \\sim C63 \\sim C64A \\sim C64: within 1.7A with sigma of 0.02
and sigma for terminal atoms of 0.04
Uanis(C77) \\sim Ueq, Uanis(C71) \\sim Ueq, Uanis(C72) \\sim Ueq, Uanis(C76)
\\sim Ueq, Uanis(C73) \\sim Ueq, Uanis(C75) \\sim Ueq, Uanis(C74) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C27) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C29) \\sim Ueq, Uanis(C30)
\\sim Ueq, Uanis(C27A) \\sim Ueq, Uanis(C28A) \\sim Ueq, Uanis(C29A) \\sim Ueq,
Uanis(C30A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C51) \\sim Ueq, Uanis(C52) \\sim Ueq, Uanis(C53) \\sim Ueq, Uanis(C51A)
\\sim Ueq, Uanis(C53A) \\sim Ueq, Uanis(C52A) \\sim Ueq, Uanis(C54) \\sim Ueq,
Uanis(C55) \\sim Ueq, Uanis(C56) \\sim Ueq, Uanis(C54A) \\sim Ueq, Uanis(C55A)
\\sim Ueq, Uanis(C56A) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C63A) \\sim Ueq, Uanis(C63) \\sim Ueq, Uanis(C64A) \\sim Ueq, Uanis(C64)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(H26C)=Sof(H26D)=Sof(C27A)=Sof(H27C)=Sof(H27D)=Sof(C28A)=Sof(H28C)=
 Sof(H28D)=Sof(C29A)=Sof(H29C)=Sof(H29D)=Sof(C30A)=Sof(H30D)=Sof(H30E)=
 Sof(H30F)=1-FVAR(1)
 Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(C28)=Sof(H28A)=Sof(H28B)=
 Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=FVAR(1)
 Sof(C51A)=Sof(H51A)=Sof(C53A)=Sof(H53D)=Sof(H53E)=Sof(H53F)=Sof(C52A)=
 Sof(H52D)=Sof(H52E)=Sof(H52F)=1-FVAR(2)
 Sof(C51)=Sof(H51)=Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(H52C)=Sof(C53)=Sof(H53A)=
 Sof(H53B)=Sof(H53C)=FVAR(2)
 Sof(C54A)=Sof(H54A)=Sof(C55A)=Sof(H55D)=Sof(H55E)=Sof(H55F)=Sof(C56A)=
 Sof(H56D)=Sof(H56E)=Sof(H56F)=1-FVAR(3)
 Sof(C54)=Sof(H54)=Sof(C55)=Sof(H55A)=Sof(H55B)=Sof(H55C)=Sof(C56)=Sof(H56A)=
 Sof(H56B)=Sof(H56C)=FVAR(3)
 Sof(H62A)=Sof(C64A)=Sof(H64D)=Sof(H64E)=Sof(H64F)=Sof(C63A)=Sof(H63D)=
 Sof(H63E)=Sof(H63F)=1-FVAR(4)
 Sof(H62)=Sof(C63)=Sof(H63A)=Sof(H63B)=Sof(H63C)=Sof(C64)=Sof(H64A)=Sof(H64B)=
 Sof(H64C)=FVAR(4)
 Fixed Sof: C71(0.5) C72(0.5) H72(0.5) C73(0.5) H73(0.5) C74(0.5) H74(0.5)
 C75(0.5) H75(0.5) C76(0.5) H76(0.5) C77(0.5) H77A(0.5) H77B(0.5) H77C(0.5)
6.a Ternary CH refined with riding coordinates:
 C51(H51), C54(H54), C57(H57), C62(H62), C62(H62A), C65(H65), C68(H68),
 C51A(H51A), C54A(H54A)
6.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,
 H19B), C20(H20A,H20B), C21(H21A,H21B), C23(H23A,H23B), C24(H24A,H24B),
 C25(H25A,H25B), C26(H26A,H26B), C26(H26C,H26D), C27(H27A,H27B), C28(H28A,H28B),
  C29(H29A,H29B), C27A(H27C,H27D), C28A(H28C,H28D), C29A(H29C,H29D)
6.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N4(H4), C3(H3A), C4(H4A), C32(H32), C36(H36), C38(H38), C39(H39),
 C40(H40), C41(H41), C43(H43), C47(H47), C72(H72), C73(H73), C74(H74), C75(H75),
  C76(H76)
6.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C30(H30A,H30B,H30C), C52(H52A,H52B,H52C), C53(H53A,H53B,
 H53C), C55(H55A,H55B,H55C), C56(H56A,H56B,H56C), C58(H58A,H58B,H58C), C59(H59A,
 H59B,H59C), C63(H63A,H63B,H63C), C64(H64A,H64B,H64C), C66(H66A,H66B,H66C),
 C67(H67A,H67B,H67C), C69(H69A,H69B,H69C), C70(H70A,H70B,H70C), C77(H77A,H77B,
 H77C), C30A(H30D,H30E,H30F), C53A(H53D,H53E,H53F), C52A(H52D,H52E,H52F),
 C55A(H55D,H55E,H55F), C56A(H56D,H56E,H56F), C64A(H64D,H64E,H64F), C63A(H63D,
 H63E,H63F)
;
_shelx_res_checksum              18399
_olex2_submission_special_instructions 'No special instructions were received'