Synthesis of Erythritol Tetranitrate (ETN) Derivatives: Functional Group Tuning of Explosive Sensitivity.
Lease, Nicholas; Kay, Lisa M.; Brown, Geoffrey W.; Chavez, David E.; Robbins, David; Byrd, Edward F. C.; Imler, Gregory H.; Parrish, Damon A.; Manner, Virginia W.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03344

data_4038071
_publ_section_title
;
 Synthesis of Erythritol Tetranitrate (ETN) Derivatives: Functional Group
 Tuning of Explosive Sensitivity.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03344
_journal_year                    2020
_chemical_formula_moiety         'C4 H10 N8 O8'
_chemical_formula_sum            'C4 H10 N8 O8'
_chemical_formula_weight         298.20
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.759(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7420(19)
_cell_length_b                   6.4525(13)
_cell_length_c                   11.1204(18)
_cell_measurement_reflns_used    3559
_cell_measurement_temperature    566(2)
_cell_measurement_theta_max      74.43
_cell_measurement_theta_min      6.81
_cell_volume                     554.9(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      566(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Photon II'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'Montel multilayer optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3997
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.538
_diffrn_reflns_theta_min         6.817
_diffrn_source                   '1uS microfocus'
_exptl_absorpt_coefficient_mu    1.507
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     97
_refine_ls_number_reflns         1071
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0496P)^2^+0.2187P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1024
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1035
_reflns_number_total             1071
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03344_si_002.cif
_cod_data_source_block           chav186
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038071
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.686
_shelx_estimated_absorpt_t_max   0.939