Radically Tunable n-Type Organic Semiconductor via Polymorph Control
Davies, Daniel William; Park, Sang Kyu; Kafle, Prapti; Chung, Hyunjoong; Yuan, Dafei; Strzalka, Joseph W.; Mannsfeld, Stefan C. B.; Wang, SuYin Grass; Chen, Yu-Sheng; Gray, Danielle L.; Zhu, Xiaozhang; Diao, Ying; Chemistry of Materials  (2021) –; doi:10.1021/acs.chemmater.0c04678

data_4003889
_publ_contact_author
; 
? 
University of Illinois 
School of Chemical Sciences, Box 59-1 
505 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
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_publ_section_title
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 Radically Tunable n-Type Organic Semiconductor via Polymorph Control
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_journal_name_full               'Chemistry of Materials'
_journal_paper_doi               10.1021/acs.chemmater.0c04678
_journal_year                    2021
_chemical_formula_moiety         'C54 H65 N5 O2 S5'
_chemical_formula_sum            'C54 H65 N5 O2 S5'
_chemical_formula_weight         976.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'dual space'
_audit_creation_date             2021-02-22
_audit_creation_method
; 
Olex2 1.3 
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226) 
;
_audit_update_record
; 
? 
;
_cell_angle_alpha                90
_cell_angle_beta                 113.034(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   50.528(7)
_cell_length_b                   10.1868(12)
_cell_length_c                   24.059(3)
_cell_measurement_reflns_used    5955
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      9.14
_cell_measurement_theta_min      2.21
_cell_volume                     11396(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2014)'
_computing_data_collection       'APEX3 V2018.7-2 (Bruker, 2018)'
_computing_data_reduction
; 
SAINT V8.38A, XPREP v2014/2, 
SADABS V2014/5 (Krause et al., 2015) 
;
_computing_molecular_graphics
; 
SHELXTL v2014-7 (Bruker, 2014), 
;
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2018-3 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004  (Burla et al.,  2007)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Pilatus
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_source         synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.41328
_diffrn_radiation_wavelength_id  9_25
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            34711
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        9.271
_diffrn_reflns_theta_max         9.271
_diffrn_reflns_theta_min         0.988
_diffrn_source_current           103.0
_diffrn_source_power             103.0
_diffrn_source_voltage           1000.0
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.7434
_exptl_absorpt_correction_T_min  0.6398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Krause et al., 2015)'
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             4160
_exptl_crystal_id                9_25
_exptl_crystal_preparation
; 
? 
;
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     560
_refine_ls_number_reflns         2821
_refine_ls_number_restraints     1595
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0766
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1838P)^2^+33.6091P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2374
_refine_ls_wR_factor_ref         0.2507
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2395
_reflns_number_total             2821
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cm0c04678_si_001.cif
_cod_data_source_block           9_25_a
_cod_original_cell_volume        11396(2)
_cod_database_code               4003889
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
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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 
2. Restrained distances 
 C3-C19 \\sim C3-C19A \\sim C16-C50 
 with sigma of 0.01 
 C19-C21 \\sim C19A-C21A \\sim C20-C22 \\sim C20A-C22A \\sim C21-C23 \\sim 
C21A-C23A \\sim C22-C24 ~ 
 C22A-C24A \\sim C50-C52 \\sim C50-C52A \\sim C51-C53 \\sim C51A-C53A \\sim 
C52-C54 \\sim C52A-C54A ~ 
 C53-C55 \\sim C53A-C55A 
 with sigma of 0.08 
 C51A-C50 \\sim C51-C50 \\sim C52A-C51A \\sim C52-C51 \\sim C53-C52 \\sim 
C53A-C52A \\sim C54A-C53A ~ 
 C54-C53 \\sim C55-C54 \\sim C55A-C54A \\sim C20-C19 \\sim C20A-C19A \\sim 
C21-C20 \\sim C21A-C20A ~ 
 C22-C21 \\sim C22A-C21A \\sim C23-C22 \\sim C23A-C22A \\sim C24A-C23A \\sim 
C24-C23 
 with sigma of 0.02 
 C40-C39 \\sim C29-C28 \\sim C29A-C28 
 with sigma of 0.01 
 C29-C31 \\sim C30-C32 \\sim C31-C33 \\sim C32-C34 \\sim C33-C35 \\sim C34-C36 
\\sim C29A-C31A \\sim C30A- 
 C32A \\sim C31A-C33A \\sim C32A-C34A \\sim C33A-C35A \\sim C34A-C36A \\sim 
C29-C39 \\sim C29A-C39A ~ 
 C38-C40 \\sim C38A-C40A \\sim C39-C41 \\sim C39A-C41A \\sim C40-C42 \\sim 
C40A-C42A \\sim C41-C43 ~ 
 C41A-C43A \\sim C42-C44 \\sim C42A-C44A \\sim C43-C45 \\sim C43A-C45A \\sim 
C44-C46 \\sim C44A-C46A 
 with sigma of 0.08 
 C36A-C35A \\sim C36-C35 \\sim C35A-C34A \\sim C35-C34 \\sim C34A-C33A \\sim 
C34-C33 \\sim C33A-C32A ~ 
 C33-C32 \\sim C32-C31 \\sim C32A-C31A \\sim C31A-C30A \\sim C31-C30 \\sim 
C30-C29 \\sim C30A-C29A ~ 
 C38-C29 \\sim C38A-C29A \\sim C39A-C38A \\sim C39-C38 \\sim C40A-C39A \\sim 
C40-C39 \\sim C41A-C40A ~ 
 C41-C40 \\sim C42-C41 \\sim C42A-C41A \\sim C43A-C42A \\sim C43-C42 \\sim 
C44A-C43A \\sim C44-C43 ~ 
 C45A-C44A \\sim C45-C44 \\sim C46-C45 \\sim C46A-C45A 
 with sigma of 0.02 
3. Uiso/Uaniso restraints and constraints 
C29 \\sim C30 \\sim C38 \\sim C39 \\sim C40 \\sim C41 \\sim C42 \\sim C29A 
\\sim H30D \\sim C38A \\sim C39A \\sim C40A \\sim C41A \\sim C43 \\sim C44 
\\sim C45 \\sim C46 \\sim C42A \\sim C43A \\sim C44A \\sim C45A \\sim C46A 
\\sim C30A \\sim C31 \\sim C31A \\sim C32 \\sim C32A \\sim C33 \\sim C33A \\sim 
C34 \\sim C34A \\sim C35 \\sim C35A \\sim C36 \\sim C36A \\sim C19 \\sim C19A 
\\sim C20A \\sim C20 \\sim C21 \\sim C21A \\sim C22 \\sim C22A \\sim C23 \\sim 
C23A \\sim C24A \\sim C24 \\sim C51 \\sim C51A \\sim C52A \\sim C52 \\sim C53 
\\sim C53A \\sim C54A \\sim C54 \\sim C55A \\sim C55: within 2A with sigma of 
0.01 and sigma for terminal atoms of 0.02 within 2A 
4. Rigid body (RIGU) restrains 
 All non-hydrogen atoms 
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 
5. Others 
 Sof(C19A)=Sof(H19C)=Sof(H19D)=Sof(C20A)=Sof(H20C)=Sof(H20D)=Sof(C21A)= 
 Sof(H21C)=Sof(H21D)=Sof(C22A)=Sof(H22C)=Sof(H22D)=Sof(C23A)=Sof(H23C)= 
 Sof(H23D)=Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(1) 
 Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C21)=Sof(H21A)= 
 Sof(H21B)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(C24)= 
 Sof(H24A)=Sof(H24B)=Sof(H24C)=FVAR(1) 
 Sof(H50C)=Sof(H50D)=Sof(C51A)=Sof(H51C)=Sof(H51D)=Sof(C52A)=Sof(H52C)= 
 Sof(H52D)=Sof(C53A)=Sof(H53C)=Sof(H53D)=Sof(C54A)=Sof(H54C)=Sof(H54D)= 
 Sof(C55A)=Sof(H55D)=Sof(H55E)=Sof(H55F)=1-FVAR(2) 
 Sof(H50A)=Sof(H50B)=Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(C52)=Sof(H52A)=Sof(H52B)= 
 Sof(C53)=Sof(H53A)=Sof(H53B)=Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(C55)=Sof(H55A)= 
 Sof(H55B)=Sof(H55C)=FVAR(2) 
 Sof(H28C)=Sof(H28D)=Sof(C29A)=Sof(H29A)=Sof(C30A)=Sof(H30C)=Sof(H30D)= 
 Sof(C31A)=Sof(H31C)=Sof(H31D)=Sof(C32A)=Sof(H32C)=Sof(H32D)=Sof(C33A)= 
 Sof(H33C)=Sof(H33D)=Sof(C34A)=Sof(H34C)=Sof(H34D)=Sof(C35A)=Sof(H35C)= 
 Sof(H35D)=Sof(C36A)=Sof(H36D)=Sof(H36E)=Sof(H36F)=Sof(C38A)=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(H42C)=Sof(H42D)=Sof(C43A)= 
 Sof(H43C)=Sof(H43D)=Sof(C44A)=Sof(H44C)=Sof(H44D)=Sof(C45A)=Sof(H45C)= 
 Sof(H45D)=Sof(C46A)=Sof(H46D)=Sof(H46E)=Sof(H46F)=1-FVAR(3) 
 Sof(H28A)=Sof(H28B)=Sof(C29)=Sof(H29)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(C31)= 
 Sof(H31A)=Sof(H31B)=Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(C33)=Sof(H33A)=Sof(H33B)= 
 Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(C36)=Sof(H36A)= 
 Sof(H36B)=Sof(H36C)=Sof(C38)=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(C43)=Sof(H43A)=Sof(H43B)=Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(C45)= 
 Sof(H45A)=Sof(H45B)=Sof(C46)=Sof(H46A)=Sof(H46B)=Sof(H46C)=FVAR(3) 
6.a Ternary CH refined with riding coordinates: 
 C29(H29), C29A(H29A) 
6.b Secondary CH2 refined with riding coordinates: 
 C28(H28A,H28B), C28(H28C,H28D), C50(H50A,H50B), C50(H50C,H50D), C19(H19A, 
 H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), 
 C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), 
  C35(H35A,H35B), C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B), C41(H41A, 
 H41B), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B), 
 C51(H51A,H51B), C52(H52A,H52B), C53(H53A,H53B), C54(H54A,H54B), C19A(H19C, 
 H19D), C20A(H20C,H20D), C21A(H21C,H21D), C22A(H22C,H22D), C23A(H23C,H23D), 
 C30A(H30C,H30D), C31A(H31C,H31D), C32A(H32C,H32D), C33A(H33C,H33D), C34A(H34C, 
 H34D), C35A(H35C,H35D), C38A(H38C,H38D), C39A(H39C,H39D), C40A(H40C,H40D), 
 C41A(H41C,H41D), C42A(H42C,H42D), C43A(H43C,H43D), C44A(H44C,H44D), C45A(H45C, 
 H45D), C51A(H51C,H51D), C52A(H52C,H52D), C53A(H53C,H53D), C54A(H54C,H54D) 
6.c Me refined with riding coordinates: 
 C24(H24A,H24B,H24C), C36(H36A,H36B,H36C), C46(H46A,H46B,H46C), C55(H55A,H55B, 
 H55C), C24A(H24D,H24E,H24F), C36A(H36D,H36E,H36F), C46A(H46D,H46E,H46F), 
 C55A(H55D,H55E,H55F) 
6.d Aromatic/amide H refined with riding coordinates: 
 C2(H2), C17(H17) 
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_shelx_res_checksum              78789
_shelx_hkl_checksum              68572
_olex2_submission_special_instructions 'No special instructions were received'