One-flask synthesis of dibenzotetraaza[14]annulene cyclic congeners bearing buta-1,3-diyne bridges
Zwoliński, K. M.; Sieroń, L.; Eilmes, J.; Organic Chemistry Frontiers 5 (2018) 171–; doi:10.1039/C7QO00821J

data_1553910
_publ_section_title
;
 One-flask synthesis of dibenzotetraaza[14]annulene cyclic congeners
 bearing buta-1,3-diyne bridges
;
_journal_issue                   2
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              171
_journal_paper_doi               10.1039/C7QO00821J
_journal_volume                  5
_journal_year                    2018
_chemical_formula_sum            'C38 H26 N4 O4'
_chemical_formula_weight         602.63
_chemical_name_systematic
;
7,16-[2,2'-(hexano-2,4-diyne-1,6-dioxy)-dibenzoylo]-5,14-dihydrodibenzo[b,i][1,4,8,11]tetraazacyclotetradecine
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-07-12 deposited with the CCDC.
2017-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.1618(16)
_cell_length_b                   11.9414(11)
_cell_length_c                   23.2097(17)
_cell_measurement_reflns_used    7864
_cell_measurement_temperature    291
_cell_measurement_theta_max      35.9327
_cell_measurement_theta_min      1.7189
_cell_volume                     5865.1(8)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      291
_diffrn_detector_area_resol_mean 8.2356
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Kuma KM-4 CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1137
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            66233
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         1.755
_diffrn_source                   'Seifert Mo tube'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       Prism
_exptl_crystal_F_000             2512
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         5176
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.0954
_refine_ls_R_factor_gt           0.0404
_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^)+0.5783P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0583
_refine_ls_wR_factor_ref         0.0619
_reflns_number_gt                2230
_reflns_number_total             5176
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00821j2.cif
_cod_data_source_block           k182
_cod_database_code               1553910
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              86898
_shelx_hkl_checksum              27863