Pyrene affixed triazoles: A new class of molecular semiconductors for robust, non-volatile resistive memory devices
Barman, Biswajit K.; Guru, Murali M.; Panda, Gaurav K.; Maji, Biplab; Vijayaraghavan, Ratheesh; Chemical Communications  (2019) –; doi:10.1039/C8CC10185J

data_7123151
_publ_section_title
;
 Pyrene affixed triazoles: A new class of molecular semiconductors for
 robust, non-volatile resistive memory devices
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC10185J
_journal_year                    2019
_chemical_formula_moiety         'C41 H25 N3'
_chemical_formula_sum            'C41 H25 N3'
_chemical_formula_weight         559.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-09 deposited with the CCDC.    2019-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.230(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1102(8)
_cell_length_b                   10.0420(5)
_cell_length_c                   22.5616(11)
_cell_measurement_reflns_used    4478
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      27.1930
_cell_measurement_theta_min      2.7030
_cell_volume                     2727.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.911
_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    -11.00 104.00   1.00   48.08    --   27.17  57.00 150.00  115
  2  \w    -50.00  66.00   1.00   48.08    --   27.17 -57.00 -90.00  116
  3  \w    -20.00  30.00   1.00   48.08    --  -25.76 -99.00   0.00   50
  4  \w     35.00 124.00   1.00   48.08    --   27.17 178.00-150.00   89
  5  \w    -11.00  14.00   1.00   48.08    --   27.17  57.00-120.00   25
  6  \w    -11.00 104.00   1.00   48.08    --   27.17  57.00 -30.00  115
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0547955000
_diffrn_orient_matrix_UB_12      -0.0163597000
_diffrn_orient_matrix_UB_13      -0.0121602000
_diffrn_orient_matrix_UB_21      0.0063459000
_diffrn_orient_matrix_UB_22      -0.0645777000
_diffrn_orient_matrix_UB_23      0.0126173000
_diffrn_orient_matrix_UB_31      -0.0206784000
_diffrn_orient_matrix_UB_32      0.0233041000
_diffrn_orient_matrix_UB_33      0.0263621000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9394
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.571
_diffrn_reflns_theta_min         1.816
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1799 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         5439
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0431P)^2^+5.7810P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1340
_refine_ls_wR_factor_ref         0.1425
_reflns_Friedel_coverage         0.889
_reflns_Friedel_fraction_full    0.952
_reflns_Friedel_fraction_max     0.811
_reflns_number_gt                4630
_reflns_number_total             5439
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc10185j2.cif
_cod_data_source_block           mmg59r
_cod_database_code               7123151
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H N'
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C008(H008), C00B(H00B), C00C(H00C), C00E(H00E), C00G(H00G),
 C00J(H00J), C00N(H00N), C00O(H00O), C00P(H00P), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U), C00W(H00W), C00Y(H00Y), C00Z(H00Z), C012(H012),
 C014(H014), C015(H015), C016(H016), C018(H018)
2.b Idealised Me refined as rotating group:
 C017(H01A,H01B,H01C)
;
_shelx_res_checksum              18747
_olex2_date_sample_data_collection 2018-05-23
_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 1.436
_oxdiff_exptl_absorpt_empirical_full_min 0.750