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_4031926
_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_formula_moiety
;
2(C26 H36 N4), 2(C H4 O), 4(Br), 3(H2 O)
;
_chemical_formula_sum            'C27 H43 Br2 N4 O2.5'
_chemical_formula_weight         623.47
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 102.826(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7180(5)
_cell_length_b                   22.6793(13)
_cell_length_c                   13.0099(7)
_cell_measurement_reflns_used    11013
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      1.8
_cell_volume                     2795.8(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    SHELXS-86
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_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  0.0771
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14043
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.641
_diffrn_reflns_theta_min         1.796
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.933
_exptl_absorpt_correction_T_max  0.7199
_exptl_absorpt_correction_T_min  0.4566
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
A face-index absorption correction was applied 
within the Stoe X-AREA suite.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_description       block
_exptl_crystal_F_000             1292
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         1.139
_refine_diff_density_min         -1.819
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5246
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0869P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1558
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3494
_reflns_number_total             5246
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02464_si_004.cif
_cod_data_source_block           shelx
_cod_original_formula_sum        'C27 H43 Br2 N4 O2.50'
_cod_database_code               4031926
_shelx_estimated_absorpt_t_min   0.372
_shelx_estimated_absorpt_t_max   0.720
_shelxl_version_number           2013-4
_shelx_res_checksum              37500
_shelx_hkl_checksum              82211