Synthesis and crystal structure of anti-10-(4-cyanophenyl)-10,11,22,23-tetrahydro-9H,21H-5,8:15,12-bis(metheno)[1,5,11]triazacyclohexadecino[1,16-a:5,6-a′]diindole dichloromethane monosolvate
Kubono, Koji; Tani, Keita; Kashiwagi, Yukiyasu; Acta Crystallographica Section E Crystallographic Communications 81 (2025) 20–23; doi:10.1107/S2056989024011782

data_2023340
_publ_section_title
;
 Synthesis and crystal structure of
 anti-10-(4-cyanophenyl)-10,11,22,23-tetrahydro-9H,21H-5,8:15,12-bis(metheno)[1,5,11]triazacyclohexadecino[1,16-a:5,6-a&#x2032;]diindole
 dichloromethane monosolvate
;
_journal_coeditor_code           OX2009
_journal_issue                   1
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first              20
_journal_page_last               23
_journal_paper_doi               10.1107/S2056989024011782
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          'C36 H28 N4, C H2 Cl2'
_chemical_formula_moiety         'C36 H28 N4, C H2 Cl2'
_chemical_formula_sum            'C37 H30 Cl2 N4'
_chemical_formula_weight         601.55
_chemical_name_common
;<i>anti</i>-4-(1^9^<i>H</i>,5^9^<i>H</i>-3-Aza-1,5(3,9)-dicarbazolacyclooctaphane-3-yl)benzonitrile (host molecule)
dichloromethane monosolvate
;
_chemical_name_systematic
;10-(4-Cyanophenyl)-10,11,22,23-tetrahydro-9<i>H</i>,21<i>H</i>-5,8:15,12-bis(metheno)[1,5,11]triazacyclohexadecino[1,16-<i>a</i>:5,6-<i>a</i>']diindole dichloromethane
monosolvate
;
_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
_audit_creation_method
;
OLEX2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.085(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.85270(10)
_cell_length_b                   28.7160(3)
_cell_length_c                   10.77540(10)
_cell_measurement_reflns_used    14622
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      76.9000
_cell_measurement_theta_min      3.0670
_cell_volume                     2881.11(6)
_computing_cell_refinement
;
<i>CrysAlis PRO</i> 1.171.42.90a (Rigaku OD, 2023)
;
_computing_data_collection
;
<i>CrysAlis PRO</i> 1.171.42.90a (Rigaku OD, 2023)
;
_computing_data_reduction
;
<i>CrysAlis PRO</i> 1.171.42.90a (Rigaku OD, 2023)
;
_computing_molecular_graphics
;
<i>PLATON</i> (Spek, 2020)
;
_computing_publication_material
;
<i>OLEX2</i> 1.5 (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
<i>SHELXL2018/3</i> (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
<i>SHELXT2018/2</i> (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      100.0(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20903
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.107
_diffrn_reflns_theta_min         3.078
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.293
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2023)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.263
_exptl_crystal_size_min          0.222
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.372
_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     388
_refine_ls_number_reflns         5741
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0420P)^2^+1.3432P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0904
_reflns_number_gt                5247
_reflns_number_total             5741
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ox2009.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2023340
_shelx_estimated_absorpt_t_min   0.556
_shelx_estimated_absorpt_t_max   0.630
_shelx_hkl_checksum              55521
_shelx_res_checksum              38822