Nitroaromatics as n-type organic semiconductors for field effect transistors.
Niazi, Muhammad Rizwan; Hamzehpoor, Ehsan; Ghamari, Pegah; Perepichka, Igor F.; Perepichka, Dmitrii F.; Chemical communications (Cambridge, England) 56 (2020) 6432–6435; doi:10.1039/d0cc01236j

data_7126452
_publ_section_title
;
 Nitroaromatics as n-type organic semiconductors for field effect
 transistors.
;
_journal_issue                   47
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6432
_journal_page_last               6435
_journal_paper_doi               10.1039/d0cc01236j
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         '2(C7 H2.5 N1.5 O2.5)'
_chemical_formula_sum            'C14 H5 N3 O5'
_chemical_formula_weight         295.21
_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             2019-09-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-16 deposited with the CCDC.	2020-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.994(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.0814(2)
_cell_length_b                   6.9825(3)
_cell_length_c                   17.0804(8)
_cell_measurement_reflns_used    5405
_cell_measurement_temperature    100
_cell_measurement_theta_max      69.996
_cell_measurement_theta_min      5.192
_cell_volume                     604.56(5)
_computing_cell_refinement
;
SAINT (2013) V8.38A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2013) V8.38A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_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    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_unetI/netI     0.0073
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15821
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.084
_diffrn_reflns_theta_min         5.192
_diffrn_source                   'Microfocus Source'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_exptl_absorpt_coefficient_mu    1.092
_exptl_absorpt_correction_T_max  0.8644
_exptl_absorpt_correction_T_min  0.8139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0731 before and 0.0338 after correction. The Ratio of minimum to maximum transmission is 0.9416. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             300
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.113
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.080
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.025
_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     236
_refine_ls_number_reflns         1152
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0727P)^2^+0.0424P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1047
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1075
_reflns_number_total             1152
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc01236j2.cif
_cod_data_source_block           per1132
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7126452.cif.
;
_cod_database_code               7126452
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.887
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O2-N2 \\sim N2-O3 \\sim O4-N3A \\sim N3A-O5A \\sim N3A-O5B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O5A \\sim O5B: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.05
N3A \\sim N3B: within 2A with sigma of 0.008 and sigma for terminal atoms of
0.04
4. Others
 Sof(O5A)=Sof(N1A)=Sof(N3A)=Sof(C1A)=Sof(H12)=0.5*(1-FVAR(2))
 Sof(O5B)=Sof(N1B)=Sof(N3B)=Sof(C1B)=Sof(H2)=0.5*FVAR(2)
 Fixed Sof: O1(0.5) O2(0.5) O3(0.5) O4(0.5) N2(0.5) C2(0.5) C3(0.5) H3(0.5)
 C4(0.5) C5(0.5) H5(0.5) C6(0.5) C7(0.5) C8(0.5) C9(0.5) H9(0.5) C10(0.5)
 C11(0.5) H11(0.5) C12(0.5) C13(0.5) C14(0.5)
5.a Riding coordinates:
 C2(H2)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C9(H9), C11(H11), C12(H12)
;
_shelx_res_checksum              77083
_shelx_hkl_checksum              94024
_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_olex2_submission_special_instructions 'No special instructions were received'