An n-type semiconducting diazaporphyrin-based hydrogen-bonded organic framework.
Sakurai, Takahiro; Tanabe, Tappei; Iguchi, Hiroaki; Li, Zhuowei; Matsuda, Wakana; Tsutsui, Yusuke; Seki, Shu; Matsuda, Ryotaro; Shinokubo, Hiroshi; Chemical science 15 (2024) 12922–12927; doi:10.1039/d4sc03455d

data_1572136
_publ_section_title
;
 An n-type semiconducting diazaporphyrin-based hydrogen-bonded organic
 framework.
;
_journal_issue                   32
_journal_name_full               'Chemical science'
_journal_page_first              12922
_journal_page_last               12927
_journal_paper_doi               10.1039/d4sc03455d
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         '2(C16 H9 N3 Ni0.5 O2), 4(C2 H3 N)'
_chemical_formula_sum            'C40 H30 N10 Ni O4'
_chemical_formula_weight         773.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-07
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-09 deposited with the CCDC.	2024-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.948(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6006(2)
_cell_length_b                   22.3585(4)
_cell_length_c                   20.9221(4)
_cell_measurement_reflns_used    10778
_cell_measurement_temperature    93
_cell_measurement_theta_max      30.7480
_cell_measurement_theta_min      2.1190
_cell_volume                     3554.97(13)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      93
_diffrn_detector                 CCD
_diffrn_detector_type            'Rigaku Saturn-N'
_diffrn_measured_fraction_theta_full 0.999
_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   -110.00  70.00   0.50    3.00    --  -20.00  45.00   0.00  360
  2  \w   -110.00  70.00   0.50    3.00    --  -20.00  45.00  90.00  360
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku VariMax Saturn'
_diffrn_measurement_method       'omega scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0229901000
_diffrn_orient_matrix_UB_12      -0.0022122000
_diffrn_orient_matrix_UB_13      -0.0329240000
_diffrn_orient_matrix_UB_21      -0.0327900000
_diffrn_orient_matrix_UB_22      0.0297024000
_diffrn_orient_matrix_UB_23      0.0005702000
_diffrn_orient_matrix_UB_31      0.0842819000
_diffrn_orient_matrix_UB_32      0.0109176000
_diffrn_orient_matrix_UB_33      -0.0081242000
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0704
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            31951
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.987
_diffrn_reflns_theta_min         2.667
_diffrn_source                   'rotating-anode X-ray tubee'
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            purple
_exptl_crystal_colour_lustre     purple
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       plate
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         10301
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.1202
_refine_ls_R_factor_gt           0.0741
_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^)+(0.0635P)^2^+4.5776P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.1761
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6975
_reflns_number_total             10301
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03455d2.cif
_cod_data_source_block           nidap-cooh-take13_autored
_cod_depositor_comments          'Adding full bibliography for 1572136.cif.'
_cod_database_code               1572136
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.899
_shelx_estimated_absorpt_t_min   0.764
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00F(H00F), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00R(H00R), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00Y(H00Y),
 C011(H011), C016(H016), C017(H017), C018(H018)
2.b Idealised Me refined as rotating group:
 C01F(H01D,H01E,H01F), C01H(H01A,H01B,H01C), C01J(H01J,H01K,H01L), C01K(H01G,
 H01H,H01I)
2.c Idealised tetrahedral OH refined as rotating group:
 O003(H003), O004(H004)
;
_shelx_res_checksum              85633
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.360
_oxdiff_exptl_absorpt_empirical_full_min 0.841