Solution-processable organic semiconductors with over 220 °C glass transition temperature: manipulating morphology using a helical polycyclic heteroaromatic motif
Fang, Lingyi; Zhang, Yuyan; Cai, Yaohang; Zhang, Jing; Wei, Yuefang; Yuan, Yi; Wang, Peng; Energy & Environmental Science 16 (2023) 5231–5242; doi:10.1039/D3EE02601A

data_1569911
_publ_section_title
;
 Solution-processable organic semiconductors with over 220 \%C glass
 transition temperature: manipulating morphology using a helical
 polycyclic heteroaromatic motif
;
_journal_issue                   11
_journal_name_full               'Energy &amp; Environmental Science'
_journal_page_first              5231
_journal_page_last               5242
_journal_paper_doi               10.1039/D3EE02601A
_journal_volume                  16
_journal_year                    2023
_chemical_formula_moiety         'C54 H57 N3'
_chemical_formula_sum            'C54 H57 N3'
_chemical_formula_weight         748.02
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-08-06 deposited with the CCDC.	2023-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.5120(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.1170(3)
_cell_length_b                   53.4561(12)
_cell_length_c                   12.9832(3)
_cell_measurement_reflns_used    9571
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      25.06
_cell_measurement_theta_min      2.41
_cell_volume                     8347.8(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       64
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            61320
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.365
_diffrn_reflns_theta_min         2.278
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1010 before and 0.0549 after correction.
The Ratio of minimum to maximum transmission is 0.9074.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       plate
_exptl_crystal_F_000             3216
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.028
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1129
_refine_ls_number_reflns         15253
_refine_ls_number_restraints     292
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0815
_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^)+(0.1209P)^2^+9.5433P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2194
_refine_ls_wR_factor_ref         0.2416
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11522
_reflns_number_total             15253
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ee02601a2.cif
_cod_data_source_block           200529_beta_c6_0ma
_cod_depositor_comments
'Adding full bibliography for 1569909--1569911.cif.'
_cod_database_code               1569911
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.974
_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
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C44-C45
 1.53 with sigma of 0.02
 C45-C46
 1.53 with sigma of 0.02
 C46-C47
 1.53 with sigma of 0.02
 C46-C47A
 1.53 with sigma of 0.02
 C47-C48
 1.53 with sigma of 0.02
 C47A-C48
 1.53 with sigma of 0.02
 C98-C99
 1.53 with sigma of 0.02
 C99-C100
 1.53 with sigma of 0.02
 C99-C1D
 1.53 with sigma of 0.02
 C100-C101
 1.53 with sigma of 0.02
 C1D-C1E
 1.53 with sigma of 0.02
 C101-C102
 1.53 with sigma of 0.02
 C1E-C102
 1.53 with sigma of 0.02
 C38-C39
 1.53 with sigma of 0.02
 C38-C39A
 1.53 with sigma of 0.02
 C39A-C40A
 1.53 with sigma of 0.02
 C39-C40
 1.53 with sigma of 0.02
 C40A-C41A
 1.53 with sigma of 0.02
 C40-C41
 1.53 with sigma of 0.02
 C41A-C42A
 1.53 with sigma of 0.02
 C41-C42
 1.53 with sigma of 0.02
 C106-C1A
 1.53 with sigma of 0.02
 C1A-C1B
 1.53 with sigma of 0.02
 C1B-C1C
 1.53 with sigma of 0.02
 C43-C45
 2.53 with sigma of 0.04
 C44-C46
 2.53 with sigma of 0.04
 C45-C47
 2.53 with sigma of 0.04
 C45-C47A
 2.53 with sigma of 0.04
 C46-C48
 2.53 with sigma of 0.04
 C98-C100
 2.53 with sigma of 0.04
 C98-C1D
 2.53 with sigma of 0.04
 C99-C101
 2.53 with sigma of 0.04
 C99-C1E
 2.53 with sigma of 0.04
 C100-C102
 2.53 with sigma of 0.04
 C1D-C102
 2.53 with sigma of 0.04
 C37-C39
 2.53 with sigma of 0.04
 C37-C39A
 2.53 with sigma of 0.04
 C38-C40A
 2.53 with sigma of 0.04
 C38-C40
 2.53 with sigma of 0.04
 C39A-C41A
 2.53 with sigma of 0.04
 C39-C41
 2.53 with sigma of 0.04
 C40A-C42A
 2.53 with sigma of 0.04
 C40-C42
 2.53 with sigma of 0.04
 C105-C1A
 2.53 with sigma of 0.04
 C106-C1B
 2.53 with sigma of 0.04
 C1A-C1C
 2.53 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C43 \\sim C44 \\sim C45 \\sim C46 \\sim C48 \\sim C47 \\sim C47A: within 1.7A
with sigma of 0.02 and sigma for terminal atoms of 0.04
C104 \\sim C105 \\sim C106 \\sim C107 \\sim C108 \\sim C109 \\sim C1A \\sim C1B
\\sim C1C: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
C97 \\sim C98 \\sim C99 \\sim C102 \\sim C100 \\sim C101 \\sim C1D \\sim C1E:
within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
C37 \\sim C38 \\sim C39 \\sim C40 \\sim C41 \\sim C42 \\sim C39A \\sim C40A
\\sim C41A \\sim C42A: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02
4. Others
 Sof(H46C)=Sof(H46D)=Sof(H48D)=Sof(H48E)=Sof(H48F)=Sof(C47A)=Sof(H47C)=
 Sof(H47D)=1-FVAR(1)
 Sof(H46A)=Sof(H46B)=Sof(C47)=Sof(H47A)=Sof(H47B)=Sof(H48A)=Sof(H48B)=
 Sof(H48C)=FVAR(1)
 Sof(H10G)=Sof(H10H)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=
 Sof(C1C)=Sof(H1CA)=Sof(H1CB)=Sof(H1CC)=1-FVAR(2)
 Sof(H10E)=Sof(H10F)=Sof(C107)=Sof(H10I)=Sof(H10J)=Sof(C108)=Sof(H10K)=
 Sof(H10L)=Sof(C109)=Sof(H10M)=Sof(H10N)=Sof(H10O)=FVAR(2)
 Sof(H99C)=Sof(H99D)=Sof(H10S)=Sof(H10T)=Sof(H10U)=Sof(C1D)=Sof(H1DA)=
 Sof(H1DB)=Sof(C1E)=Sof(H1EA)=Sof(H1EB)=1-FVAR(3)
 Sof(H99A)=Sof(H99B)=Sof(H10P)=Sof(H10Q)=Sof(H10R)=Sof(C101)=Sof(H10V)=
 Sof(H10W)=Sof(C100)=Sof(H10X)=Sof(H10Y)=FVAR(3)
 Sof(H38C)=Sof(H38D)=Sof(C39A)=Sof(H39C)=Sof(H39D)=Sof(C40A)=Sof(H40C)=
 Sof(H40D)=Sof(C41A)=Sof(H41C)=Sof(H41D)=Sof(C42A)=Sof(H42D)=Sof(H42E)=
 Sof(H42F)=1-FVAR(4)
 Sof(H38A)=Sof(H38B)=Sof(C39)=Sof(H39A)=Sof(H39B)=Sof(C40)=Sof(H40A)=Sof(H40B)=
 Sof(C41)=Sof(H41A)=Sof(H41B)=Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(H42C)=FVAR(4)
5.a Secondary CH2 refined with riding coordinates:
 C91(H91A,H91B), C49(H49A,H49B), C43(H43A,H43B), C37(H37A,H37B), C104(H10A,
 H10B), C44(H44A,H44B), C92(H92A,H92B), C97(H97A,H97B), C45(H45A,H45B),
 C50(H50A,H50B), C105(H10C,H10D), C98(H98A,H98B), C46(H46A,H46B), C46(H46C,
 H46D), C93(H93A,H93B), C51(H51A,H51B), C52(H52A,H52B), C94(H94A,H94B),
 C38(H38A,H38B), C38(H38C,H38D), C53(H53A,H53B), C106(H10E,H10F), C106(H10G,
 H10H), C95(H95A,H95B), C47(H47A,H47B), C39(H39A,H39B), C99(H99A,H99B),
 C99(H99C,H99D), C40(H40B,H40A), C107(H10J,H10I), C108(H10K,H10L), C41(H41A,
 H41B), C101(H10V,H10W), C100(H10X,H10Y), C47A(H47C,H47D), C1A(H1AB,H1AA),
 C1B(H1BA,H1BB), C1D(H1DA,H1DB), C1E(H1EA,H1EB), C39A(H39C,H39D), C40A(H40C,
 H40D), C41A(H41C,H41D)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C33(H33), C30(H30), C29(H29), C19(H19), C63(H63), C36(H36), C64(H64),
 C2(H2), C77(H77), C20(H20), C4(H4), C34(H34), C23(H23), C55(H55), C3(H3),
 C35(H35), C9(H9), C58(H58), C26(H26), C10(H10), C78(H78), C24(H24), C25(H25),
 C79(H79), C74(H74), C56(H56), C57(H57), C80(H80), C73(H73), C87(H87), C88(H88),
  C83(H83), C89(H89), C90(H90), C84(H84)
5.c Idealised Me refined as rotating group:
 C96(H96A,H96B,H96C), C54(H54A,H54B,H54C), C48(H48A,H48B,H48C), C48(H48D,H48E,
 H48F), C109(H10M,H10N,H10O), C102(H10P,H10Q,H10R), C102(H10S,H10T,H10U),
 C42(H42A,H42B,H42C), C1C(H1CB,H1CA,H1CC), C42A(H42D,H42E,H42F)
;
_shelx_res_checksum              71140
_olex2_submission_special_instructions 'No special instructions were received'