#------------------------------------------------------------------------------
#$Date: 2020-02-08 01:45:55 +0200 (Sat, 08 Feb 2020) $
#$Revision: 247956 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/41/4134132.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4134132
loop_
_publ_author_name
'Huang, Wei'
'Tang, Yongxing'
'Imler, Gregory H.'
'Parrish, Damon A.'
'Shreeve, Jean'ne M.'
_publ_section_title
;
 Nitrogen-Rich Tetrazolo[1,5-b]pyridazine: Promising Building Block for
 Advanced Energetic Materials.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c00161
_journal_year                    2020
_chemical_formula_moiety         'C4 H4 N8 O2, C2 H6 O S'
_chemical_formula_sum            'C6 H10 N8 O3 S'
_chemical_formula_weight         274.28
_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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.5446(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1503(6)
_cell_length_b                   5.3942(3)
_cell_length_c                   22.8539(14)
_cell_measurement_reflns_used    3631
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.38
_cell_measurement_theta_min      2.44
_cell_volume                     1126.92(12)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω 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  0.0324
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            12840
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.980
_diffrn_reflns_theta_min         1.784
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3200
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0439
_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/[σ²(Fo²)+(0.0611P)²+0.4055P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1228
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2397
_reflns_number_total             3200
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c00161_si_003.cif
_cod_data_source_block           shrv776
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4134132
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.40504(16) 0.0343(3) 0.44840(6) 0.0466(4) Uani 1 1 d . .
O2 O 0.27051(16) 0.0361(3) 0.36842(6) 0.0471(4) Uani 1 1 d . .
N3 N 0.30741(16) 0.1259(3) 0.41595(6) 0.0314(3) Uani 1 1 d . .
C4 C 0.23414(17) 0.3422(3) 0.43492(7) 0.0274(3) Uani 1 1 d . .
C5 C 0.26348(17) 0.4474(3) 0.49007(7) 0.0267(3) Uani 1 1 d . .
N6 N 0.36018(17) 0.3654(3) 0.52998(6) 0.0365(3) Uani 1 1 d . .
H6A H 0.4118 0.2364 0.5230 0.044 Uiso 1 1 calc R U
H6B H 0.3717 0.4411 0.5630 0.044 Uiso 1 1 calc R U
C7 C 0.17620(18) 0.6707(3) 0.50467(7) 0.0286(3) Uani 1 1 d . .
N8 N 0.20017(19) 0.7821(3) 0.55664(7) 0.0412(4) Uani 1 1 d . .
H8A H 0.1495 0.9098 0.5656 0.049 Uiso 1 1 calc R U
H8B H 0.2663 0.7258 0.5811 0.049 Uiso 1 1 calc R U
N9 N 0.07412(17) 0.7656(3) 0.46955(6) 0.0350(3) Uani 1 1 d . .
N10 N 0.05343(15) 0.6465(3) 0.41788(6) 0.0318(3) Uani 1 1 d . .
N11 N -0.04950(18) 0.7247(3) 0.37810(7) 0.0438(4) Uani 1 1 d . .
N12 N -0.0408(2) 0.5734(4) 0.33438(8) 0.0499(4) Uani 1 1 d . .
N13 N 0.06406(18) 0.3988(3) 0.34379(7) 0.0429(4) Uani 1 1 d . .
C14 C 0.12283(18) 0.4471(3) 0.39694(7) 0.0293(3) Uani 1 1 d . .
O15 O 0.42365(18) 0.5979(3) 0.63630(6) 0.0495(4) Uani 1 1 d . .
S16 S 0.41529(5) 0.50537(9) 0.69861(2) 0.03779(14) Uani 1 1 d . .
C17 C 0.3950(3) 0.1780(4) 0.69327(9) 0.0484(5) Uani 1 1 d . .
H17A H 0.3023 0.1395 0.6741 0.073 Uiso 1 1 calc R U
H17B H 0.3995 0.1069 0.7318 0.073 Uiso 1 1 calc R U
H17C H 0.4723 0.1109 0.6710 0.073 Uiso 1 1 calc R U
C18 C 0.5982(3) 0.5141(5) 0.72750(10) 0.0581(6) Uani 1 1 d . .
H18A H 0.6591 0.4163 0.7033 0.087 Uiso 1 1 calc R U
H18B H 0.6022 0.4483 0.7666 0.087 Uiso 1 1 calc R U
H18C H 0.6324 0.6824 0.7283 0.087 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 N3 O1 122.51(15)
O2 N3 C4 118.69(14)
O1 N3 C4 118.79(14)
C5 C4 N3 122.25(14)
C5 C4 C14 119.44(14)
N3 C4 C14 118.25(14)
N6 C5 C4 125.73(15)
N6 C5 C7 117.75(14)
C4 C5 C7 116.52(14)
C5 N6 H6A 120.0
C5 N6 H6B 120.0
H6A N6 H6B 120.0
N9 C7 N8 116.91(15)
N9 C7 C5 123.61(15)
N8 C7 C5 119.47(15)
C7 N8 H8A 120.0
C7 N8 H8B 120.0
H8A N8 H8B 120.0
C7 N9 N10 114.77(14)
N11 N10 C14 109.66(14)
N11 N10 N9 120.52(14)
C14 N10 N9 129.82(14)
N12 N11 N10 104.96(15)
N11 N12 N13 112.52(15)
C14 N13 N12 105.25(15)
N13 C14 N10 107.60(15)
N13 C14 C4 136.57(16)
N10 C14 C4 115.82(14)
O15 S16 C18 104.79(10)
O15 S16 C17 105.79(9)
C18 S16 C17 98.38(12)
S16 C17 H17A 109.5
S16 C17 H17B 109.5
H17A C17 H17B 109.5
S16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
S16 C18 H18A 109.5
S16 C18 H18B 109.5
H18A C18 H18B 109.5
S16 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N3 1.2383(19)
O2 N3 1.2230(19)
N3 C4 1.423(2)
C4 C5 1.397(2)
C4 C14 1.426(2)
C5 N6 1.319(2)
C5 C7 1.492(2)
N6 H6A 0.8600
N6 H6B 0.8600
C7 N9 1.308(2)
C7 N8 1.340(2)
N8 H8A 0.8600
N8 H8B 0.8600
N9 N10 1.350(2)
N10 N11 1.347(2)
N10 C14 1.348(2)
N11 N12 1.295(2)
N12 N13 1.355(2)
N13 C14 1.332(2)
O15 S16 1.5143(14)
S16 C18 1.772(2)
S16 C17 1.780(2)
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6A O1 0.86 2.02 2.627(2) 126.6 .
N6 H6A O1 0.86 2.30 3.0683(19) 149.5 3_656
N6 H6B O15 0.86 1.92 2.773(2) 172.5 .
N8 H8A N11 0.86 2.55 3.374(2) 161.7 3_576
N8 H8B O15 0.86 2.00 2.855(2) 178.5 .
C17 H17A N11 0.96 2.66 3.532(3) 151.5 3_566
C17 H17B N12 0.96 2.57 3.524(3) 170.2 4_666
C18 H18B N13 0.96 2.61 3.492(3) 153.4 4_666
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O2 N3 C4 C5 176.01(16)
O1 N3 C4 C5 -3.3(2)
O2 N3 C4 C14 -1.2(2)
O1 N3 C4 C14 179.46(16)
N3 C4 C5 N6 0.8(3)
C14 C4 C5 N6 178.05(16)
N3 C4 C5 C7 -178.71(14)
C14 C4 C5 C7 -1.5(2)
N6 C5 C7 N9 -177.95(17)
C4 C5 C7 N9 1.6(2)
N6 C5 C7 N8 1.1(2)
C4 C5 C7 N8 -179.28(15)
N8 C7 N9 N10 -179.67(15)
C5 C7 N9 N10 -0.5(2)
C7 N9 N10 N11 179.39(16)
C7 N9 N10 C14 -0.7(3)
C14 N10 N11 N12 0.0(2)
N9 N10 N11 N12 179.91(16)
N10 N11 N12 N13 -0.1(2)
N11 N12 N13 C14 0.2(2)
N12 N13 C14 N10 -0.1(2)
N12 N13 C14 C4 179.1(2)
N11 N10 C14 N13 0.1(2)
N9 N10 C14 N13 -179.80(17)
N11 N10 C14 C4 -179.31(15)
N9 N10 C14 C4 0.8(3)
C5 C4 C14 N13 -178.7(2)
N3 C4 C14 N13 -1.4(3)
C5 C4 C14 N10 0.4(2)
N3 C4 C14 N10 177.76(14)
