Resolving Synthetic Challenges Faced in the Syntheses of Asymmetric N,N’-Ethylene-Bridged Energetic Compounds
Shreeve, Jean'ne M.; Kumar, Dheeraj; Imler, Gregory H.; Parrish, Damon A.; New J. Chem. 41 (2017) 4040–4047; doi:10.1039/C7NJ00327G

data_7056099
_publ_section_title
;
 Resolving Synthetic Challenges Faced in the Syntheses of Asymmetric
 N,N&#x2019;-Ethylene-Bridged Energetic Compounds
;
_journal_issue                   10
_journal_name_full               'New J. Chem.'
_journal_page_first              4040
_journal_page_last               4047
_journal_paper_doi               10.1039/C7NJ00327G
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         'C6 H6 N12 O4'
_chemical_formula_sum            'C6 H6 N12 O4'
_chemical_formula_weight         310.23
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc1mhn0s
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-09-16 deposited with the CCDC.
2017-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.054(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5577(7)
_cell_length_b                   31.045(3)
_cell_length_c                   5.8420(6)
_cell_measurement_reflns_used    6044
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.908
_cell_measurement_theta_min      2.625
_cell_volume                     1184.7(2)
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            15752
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.966
_diffrn_reflns_theta_min         2.624
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0413P)^2^+0.4590P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0909
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2825
_reflns_number_total             3348
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7nj00327g2.cif
_cod_data_source_block           shrv440
_cod_database_code               7056099
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.997