Mono- and Bis-Alkylation of Glyoxal-Bridged Tetraazamacrocycles Using Mechanochemistry.
Abdulwahaab, Bassim H.; Burke, Benjamin P.; Domarkas, Juozas; Silversides, Jon D.; Prior, Timothy J.; Archibald, Stephen J.; The Journal of organic chemistry 81 (2016) 890–898; doi:10.1021/acs.joc.5b02464

data_4031928
_publ_section_title
;
 Mono- and Bis-Alkylation of Glyoxal-Bridged Tetraazamacrocycles Using
 Mechanochemistry.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              890
_journal_page_last               898
_journal_paper_doi               10.1021/acs.joc.5b02464
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety
;
C28 H40 N4, 2(Br), H2 O
;
_chemical_formula_sum            'C28 H42 Br2 N4 O'
_chemical_formula_weight         610.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7048(7)
_cell_length_b                   13.9924(8)
_cell_length_c                   18.8717(13)
_cell_measurement_reflns_used    8038
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.8
_cell_measurement_theta_min      2.15
_cell_volume                     2826.7(3)
_computing_cell_refinement       'Stoe X-AREA'
_computing_data_collection       'Stoe X-AREA'
_computing_data_reduction        'Stoe X-AREA'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    SHEXLS-86
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Stoe IPDS2'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1380
_diffrn_reflns_av_unetI/netI     0.1193
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10839
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.282
_diffrn_reflns_theta_min         2.396
_diffrn_source                   'fine-focus X-ray tube'
_exptl_absorpt_coefficient_mu    2.895
_exptl_absorpt_correction_T_max  0.7161
_exptl_absorpt_correction_T_min  0.3802
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
Face-index absorption correction in Stoe X-AREA suite
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.827
_refine_diff_density_min         -0.914
_refine_diff_density_rms         0.163
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.20(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3821
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.914
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0626
_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^)+(0.0825P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.1532
_reflns_Friedel_coverage         0.794
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2555
_reflns_number_total             3821
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02464_si_002.cif
_cod_data_source_block           ba75b
_cod_database_code               4031928
_shelx_estimated_absorpt_t_min   0.391
_shelx_estimated_absorpt_t_max   0.761
_shelxl_version_number           2013-4
_shelx_res_checksum              72944
_shelx_hkl_checksum              87997