Acid dyeing for green solvent processing of solvent resistant semiconducting organic thin films
Harding, Cayley R.; Cann, Jonathan; Laventure, Audrey; Sadeghianlemraski, Mozhgan; Abd-Ellah, Marwa; Rao, Keerthan R.; Gelfand, Benjamin Sidney; Aziz, Hany; Kaake, Loren; Risko, Chad; Welch, Gregory C.; Materials Horizons 7 (2020) 2959–2969; doi:10.1039/D0MH00785D

data_1558890
_publ_section_title
;
 Acid dyeing for green solvent processing of solvent resistant
 semiconducting organic thin films
;
_journal_issue                   11
_journal_name_full               'Materials Horizons'
_journal_page_first              2959
_journal_page_last               2969
_journal_paper_doi               10.1039/D0MH00785D
_journal_volume                  7
_journal_year                    2020
_chemical_formula_moiety         'C34 H29 N3 O4'
_chemical_formula_sum            'C34 H29 N3 O4'
_chemical_formula_weight         543.60
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-10 deposited with the CCDC.	2020-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.881(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.2166(7)
_cell_length_b                   18.5973(10)
_cell_length_c                   7.8095(2)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    173
_cell_measurement_theta_max      65.132
_cell_measurement_theta_min      3.413
_cell_volume                     2620.71(19)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            22039
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        65.226
_diffrn_reflns_theta_max         65.226
_diffrn_reflns_theta_min         2.449
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0995 before and 0.0345 after correction. The Ratio of minimum to maximum transmission is 0.8787. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       rod
_exptl_crystal_F_000             1144
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dioxane, methanol'
_exptl_crystal_size_max          0.358
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         4467
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0581
_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^)+(0.0847P)^2^+2.2686P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1587
_refine_ls_wR_factor_ref         0.1639
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3893
_reflns_number_total             4467
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0mh00785d2.cif
_cod_data_source_block           nhpdi
_cod_depositor_comments          'Adding full bibliography for 1558890.cif.'
_cod_database_code               1558890
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.779
_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.a Ternary CH refined with riding coordinates:
 C27(H27), C32(H32)
2.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C28(H28A,H28B), C33(H33A,H33B), C31(H31A,H31B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C11(H11), C12(H12), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C29(H29A,H29B,H29C), C34(H34A,H34B,H34C), C30(H30A,H30B,
 H30C)
;
_shelx_res_checksum              62893
_shelx_hkl_checksum              23632
_olex2_submission_special_instructions 'No special instructions were received'