An efficient ultrasonic-mediated one-pot synthesis of 2,3,6,7,9-pentaazabicyclo[3.3.1]nonanes via a N,N-dimethylformamide dimethylacetal catalyzed Mannich-like reaction
Behbehani, Haider; Ibrahim, Hamada Mohamed; RSC Advances 6 (2016) 52700–; doi:10.1039/C6RA09210A

data_7236221
_publ_section_title
;
 An efficient ultrasonic-mediated one-pot synthesis of
 2,3,6,7,9-pentaazabicyclo[3.3.1]nonanes via a N,N-dimethylformamide
 dimethylacetal catalyzed Mannich-like reaction
;
_journal_issue                   58
_journal_name_full               'RSC Advances'
_journal_page_first              52700
_journal_paper_doi               10.1039/C6RA09210A
_journal_volume                  6
_journal_year                    2016
_chemical_formula_sum            'C30 H19 Cl4 N5 O2'
_chemical_formula_weight         623.30
_chemical_name_common            Hamada_167_19_10_15
_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     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2016-03-29 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.014(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.2707(5)
_cell_length_b                   26.2035(8)
_cell_length_c                   12.8526(4)
_cell_measurement_reflns_used    4452
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      49.1995
_cell_measurement_theta_min      3.0857
_cell_volume                     5759.7(3)
_computing_cell_refinement       'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_data_collection       'Bruker Instrument Service v2012.4.0.0'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker X8 Prospector'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1416
_diffrn_reflns_av_sigmaI/netI    0.1551
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            36273
_diffrn_reflns_theta_full        66.62
_diffrn_reflns_theta_max         66.62
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    4.048
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Flake
_exptl_crystal_F_000             2544
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.633
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     739
_refine_ls_number_reflns         9976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1869
_refine_ls_R_factor_gt           0.0890
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1635P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2411
_refine_ls_wR_factor_ref         0.3199
_reflns_number_gt                4495
_reflns_number_total             9976
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra09210a1.cif
_cod_data_source_block           I
_cod_database_code               7236221