Synthesis, crystal structure and charge transport characteristics of stable <i>peri</i>-tetracene analogues.
Mamada, Masashi; Nakamura, Ryota; Adachi, Chihaya; Chemical science 12 (2020) 552–558; doi:10.1039/d0sc04699j

data_1559358
_publ_section_title
;
 Synthesis, crystal structure and charge transport characteristics of
 stable <i>peri</i>-tetracene analogues.
;
_journal_issue                   2
_journal_name_full               'Chemical science'
_journal_page_first              552
_journal_page_last               558
_journal_paper_doi               10.1039/d0sc04699j
_journal_volume                  12
_journal_year                    2020
_chemical_formula_moiety         'C H2 Cl2, C54 H38 O2'
_chemical_formula_sum            'C55 H40 Cl2 O2'
_chemical_formula_weight         803.77
_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             2020-07-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_audit_update_record
;
2020-08-25 deposited with the CCDC.	2020-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.230(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5132(6)
_cell_length_b                   21.9543(9)
_cell_length_c                   12.9943(6)
_cell_measurement_reflns_used    9588
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.1170
_cell_measurement_theta_min      2.1720
_cell_volume                     4129.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -94.00 -53.00   0.50    5.00    --  -10.30  45.00   0.00   82
  2  \w    -37.00  39.00   0.50    5.00    --  -10.30  45.00   0.00  152
  3  \w    -99.00  75.00   0.50    5.00    --  -10.30  45.00  60.00  348
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC HyPix-6000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0487653000
_diffrn_orient_matrix_UB_12      -0.0027589000
_diffrn_orient_matrix_UB_13      0.0010199000
_diffrn_orient_matrix_UB_21      -0.0040438000
_diffrn_orient_matrix_UB_22      -0.0322019000
_diffrn_orient_matrix_UB_23      0.0011718000
_diffrn_orient_matrix_UB_31      -0.0026875000
_diffrn_orient_matrix_UB_32      -0.0006004000
_diffrn_orient_matrix_UB_33      -0.0546733000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            36370
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.233
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              FR-E+
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.782
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       prism
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.279
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     538
_refine_ls_number_reflns         9472
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0717P)^2^+1.6348P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1397
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7137
_reflns_number_total             9472
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc04699j2.cif
_cod_data_source_block           compound5b
_cod_depositor_comments
;

 Adding full bibliography for 1559358--1559359.cif.

2022-09-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C110 H80 Cl4 O4'
_cod_original_formula_weight         1607.54
_cod_original_formula_moiety         '2(C H2 Cl2), 2(C54 H38 O2)'
_cod_original_formula_units_Z            2
_cod_database_code               1559358
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     100K
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 Secondary CH2 refined with riding coordinates:
 C55(H55A,H55B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C13(H13), C14(H14), C15(H15), C16(H16),
 C21(H21), C23(H23), C31(H31), C32(H32), C33(H33), C34(H34), C40(H40), C41(H41),
  C42(H42), C43(H43), C48(H48), C50(H50)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C52(H52A,H52B,
 H52C), C53(H53A,H53B,H53C), C54(H54A,H54B,H54C)
;
_shelx_res_checksum              29941
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.234
_oxdiff_exptl_absorpt_empirical_full_min 0.710