Impact of Stereo- and Regiochemistry on Energetic Materials.
Barton, Lisa M.; Edwards, Jacob T.; Johnson, Eric C.; Bukowski, Eric J.; Sausa, Rosario C.; Byrd, Edward F. C.; Orlicki, Joshua A.; Sabatini, Jesse J.; Baran, Phil S.; Journal of the American Chemical Society 141 (2019) 12531–12535; doi:10.1021/jacs.9b06961

data_4127773
_publ_section_title
;
 Impact of Stereo- and Regiochemistry on Energetic Materials.
;
_journal_issue                   32
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12531
_journal_page_last               12535
_journal_paper_doi               10.1021/jacs.9b06961
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C8 H12 N4 O12'
_chemical_formula_sum            'C8 H12 N4 O12'
_chemical_formula_weight         356.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-31
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.751(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8079(4)
_cell_length_b                   9.3371(3)
_cell_length_c                   12.0047(4)
_cell_measurement_reflns_used    3438
_cell_measurement_temperature    298.00(10)
_cell_measurement_theta_max      26.2470
_cell_measurement_theta_min      2.6900
_cell_volume                     1428.40(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0945
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     57.00 116.00   1.00    4.78    --   25.07 178.00-150.00   59
  2  \w      1.00  78.00   1.00    4.78    --   25.07 -99.00 -30.00   77
  3  \w   -114.00  60.00   1.00    4.78    --  -26.94   0.00 -90.00  174
  4  \w     57.00  99.00   1.00    4.78    --   25.07 178.00 -30.00   42
  5  \w   -107.00  14.00   1.00    4.78    --  -26.94 -77.00-120.00  121
  6  \w   -101.00   8.00   1.00    4.78    --  -26.94 -57.00 120.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dualflex, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0117929000
_diffrn_orient_matrix_UB_12      0.0687473000
_diffrn_orient_matrix_UB_13      -0.0205682000
_diffrn_orient_matrix_UB_21      -0.0414333000
_diffrn_orient_matrix_UB_22      0.0299958000
_diffrn_orient_matrix_UB_23      0.0274389000
_diffrn_orient_matrix_UB_31      0.0353410000
_diffrn_orient_matrix_UB_32      0.0122946000
_diffrn_orient_matrix_UB_33      0.0483609000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5975
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.704
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_description       irregular
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0209(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1460
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0420P)^2^+0.6530P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0901
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1346
_reflns_number_total             1460
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b06961_si_004.cif
_cod_data_source_block           all-cis-TNCB
_cod_database_code               4127773
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
;
_shelx_res_checksum              63379
_shelx_hkl_checksum              81556
_shelx_shelxl_version_number     2016/4
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.295
_oxdiff_exptl_absorpt_empirical_full_min 0.826