#------------------------------------------------------------------------------
#$Date: 2020-04-08 03:56:53 +0200 (Wed 08 de Apr de 2020) $
#$Revision: 250475 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/02/7240274.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_7240274
loop_
_publ_author_name
'Geng, Wenjing'
'Jia, Yunfei'
'Chen, Ya'
'Ma, Qing'
'Fan, Guijuan'
'Liao, Longyu'
_publ_section_title
;
 Superior thermally robust energetic materials featuring Z-E isomeric
 bis(3,4-diamino-1,2,4-triazol-5-yl)-1H-pyrazole: self-assembly
 nitrogen-rich tubes and templates with Hofmeister anions capture
 architecture
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00278J
_journal_year                    2020
_chemical_formula_moiety         'O4 S, 3(H2 O), C7 H12 N12'
_chemical_formula_sum            'C7 H18 N12 O7 S'
_chemical_formula_weight         414.39
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2020-04-04 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.193(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6062(7)
_cell_length_b                   10.0221(11)
_cell_length_c                   24.619(3)
_cell_measurement_reflns_used    1385
_cell_measurement_temperature    173
_cell_measurement_theta_max      23.087
_cell_measurement_theta_min      2.625
_cell_volume                     1623.3(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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_temperature      173
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0870
_diffrn_reflns_av_unetI/netI     0.1042
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9494
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.395
_diffrn_reflns_theta_min         1.661
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0877 before and 0.0675 after correction. The Ratio of minimum to maximum transmission is 0.8330. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3227
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1197
_refine_ls_R_factor_gt           0.0574
_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/[σ²(Fo²)+(0.0720P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1587
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1891
_reflns_number_total             3227
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00278j2.cif
_cod_data_source_block           mo_20180085-ma-32_0m
_cod_database_code               7240274
_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_max   0.992
_shelx_estimated_absorpt_t_min   0.961
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 O7-H7B
 0.85 with sigma of 0.02
 O5-H5B \\sim O5-H5A
 with sigma of 0.02
3.a Free rotating group:
 O5(H5A), O6(H6A,H6B), O7(H7A)
3.b Rotating group:
 N2(H2A,H2B), N10(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 N6(H6), N4(H4), N9(H9), C4(H4A)
3.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N11(H11A,H11B)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.52620(16) 0.72465(10) 0.32657(4) 0.0170(3) Uani 1 1 d . . . . .
O1 O 0.5005(5) 0.7988(3) 0.37654(11) 0.0266(8) Uani 1 1 d . . . . .
O3 O 0.3295(4) 0.7124(3) 0.29372(12) 0.0261(7) Uani 1 1 d . . . . .
O5 O 0.0387(5) 0.8344(3) 0.35481(13) 0.0286(8) Uani 1 1 d D . . . .
H5A H -0.0774 0.8088 0.3410 0.043 Uiso 1 1 d DG . . . .
O4 O 0.6681(4) 0.7979(3) 0.29377(12) 0.0237(7) Uani 1 1 d . . . . .
O2 O 0.6106(5) 0.5914(3) 0.33978(11) 0.0262(7) Uani 1 1 d . . . . .
N007 N 0.1911(5) 0.3000(3) 0.36930(13) 0.0160(8) Uani 1 1 d . . . . .
N3 N 0.2707(5) 0.8010(3) 0.51701(12) 0.0148(8) Uani 1 1 d . . . . .
N7 N 0.2459(6) 0.3295(3) 0.51931(13) 0.0203(8) Uani 1 1 d . . . . .
O6 O 0.8348(5) 0.4283(3) 0.27437(13) 0.0321(8) Uani 1 1 d . . . . .
H6A H 0.7491 0.4729 0.2906 0.048 Uiso 1 1 d G . . . .
H6B H 0.7671 0.3629 0.2602 0.048 Uiso 1 1 d G . . . .
N6 N 0.2735(5) 0.4391(3) 0.54933(13) 0.0193(8) Uani 1 1 d . . . . .
H6 H 0.2956 0.4390 0.5851 0.023 Uiso 1 1 calc R . . . .
N5 N 0.3351(5) 0.6998(3) 0.59628(13) 0.0209(8) Uani 1 1 d . . . . .
N2 N 0.2146(6) 0.8326(3) 0.46245(13) 0.0224(8) Uani 1 1 d . . . . .
H2A H 0.3092 0.8071 0.4425 0.027 Uiso 1 1 d GR . . . .
H2B H 0.1024 0.7924 0.4510 0.027 Uiso 1 1 d GR . . . .
N4 N 0.3446(6) 0.8364(3) 0.60227(13) 0.0232(9) Uani 1 1 d . . . . .
H4 H 0.3752 0.8775 0.6335 0.028 Uiso 1 1 calc R . . . .
N1 N 0.2899(5) 1.0272(3) 0.54454(14) 0.0237(9) Uani 1 1 d . . . . .
H1A H 0.3117 1.0853 0.5712 0.028 Uiso 1 1 calc R . . . .
H1B H 0.2600 1.0552 0.5109 0.028 Uiso 1 1 calc R . . . .
N9 N 0.1409(5) 0.0909(3) 0.38169(13) 0.0213(8) Uani 1 1 d . . . . .
H9 H 0.1193 0.0054 0.3755 0.026 Uiso 1 1 calc R . . . .
N8 N 0.1575(6) 0.1481(3) 0.43294(13) 0.0215(8) Uani 1 1 d . . . . .
N11 N 0.1523(6) 0.1626(4) 0.28998(13) 0.0271(9) Uani 1 1 d . . . . .
H11A H 0.1298 0.0822 0.2764 0.033 Uiso 1 1 calc R . . . .
H11B H 0.1684 0.2305 0.2681 0.033 Uiso 1 1 calc R . . . .
O7 O 0.6505(8) 0.0668(4) 0.29966(13) 0.0544(12) Uani 1 1 d D . . . .
H7A H 0.6507 0.1179 0.2721 0.082 Uiso 1 1 d G . . . .
N10 N 0.2138(6) 0.4254(3) 0.34690(15) 0.0298(9) Uani 1 1 d . . . . .
H10A H 0.3334 0.4317 0.3349 0.036 Uiso 1 1 d GR . . . .
H10B H 0.1230 0.4392 0.3196 0.036 Uiso 1 1 d GR . . . .
C1 C 0.3020(6) 0.8984(4) 0.55493(16) 0.0167(9) Uani 1 1 d . . . . .
C3 C 0.2638(6) 0.5511(4) 0.51849(15) 0.0146(9) Uani 1 1 d . . . . .
C2 C 0.2901(6) 0.6811(4) 0.54406(16) 0.0163(9) Uani 1 1 d . . . . .
C6 C 0.1880(6) 0.2736(4) 0.42427(15) 0.0152(8) Uani 1 1 d . . . . .
C5 C 0.2189(6) 0.3746(4) 0.46745(15) 0.0156(9) Uani 1 1 d . . . . .
C7 C 0.1616(7) 0.1813(4) 0.34283(16) 0.0190(9) Uani 1 1 d . . . . .
C4 C 0.2305(6) 0.5125(4) 0.46486(16) 0.0186(9) Uani 1 1 d . . . . .
H4A H 0.2184 0.5676 0.4333 0.022 Uiso 1 1 calc R . . . .
H5B H 0.130(6) 0.797(5) 0.3380(19) 0.045(17) Uiso 1 1 d D . . . .
H7B H 0.660(7) -0.017(2) 0.299(2) 0.041(15) Uiso 1 1 d D . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O3 109.95(18) . . ?
O1 S1 O4 109.51(18) . . ?
O1 S1 O2 110.25(17) . . ?
O3 S1 O4 108.17(17) . . ?
O2 S1 O3 110.08(18) . . ?
O2 S1 O4 108.85(17) . . ?
H5A O5 H5B 109.4 . . ?
C6 N007 N10 125.1(3) . . ?
C7 N007 N10 128.1(3) . . ?
C7 N007 C6 106.7(3) . . ?
C1 N3 N2 120.7(3) . . ?
C1 N3 C2 107.1(3) . . ?
C2 N3 N2 132.0(3) . . ?
N6 N7 C5 104.4(3) . . ?
H6A O6 H6B 104.5 . . ?
N7 N6 H6 123.9 . . ?
N7 N6 C3 112.1(3) . . ?
C3 N6 H6 123.9 . . ?
C2 N5 N4 104.6(3) . . ?
N3 N2 H2A 109.6 . . ?
N3 N2 H2B 110.6 . . ?
H2A N2 H2B 108.5 . . ?
N5 N4 H4 124.2 . . ?
C1 N4 N5 111.5(3) . . ?
C1 N4 H4 124.2 . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
N8 N9 H9 124.2 . . ?
C7 N9 H9 124.2 . . ?
C7 N9 N8 111.6(3) . . ?
C6 N8 N9 104.7(3) . . ?
H11A N11 H11B 120.0 . . ?
C7 N11 H11A 120.0 . . ?
C7 N11 H11B 120.0 . . ?
H7A O7 H7B 124.7 . . ?
N007 N10 H10A 109.6 . . ?
N007 N10 H10B 111.0 . . ?
H10A N10 H10B 108.1 . . ?
N4 C1 N3 106.0(3) . . ?
N1 C1 N3 124.8(4) . . ?
N1 C1 N4 129.3(4) . . ?
N6 C3 C2 120.2(3) . . ?
N6 C3 C4 107.5(4) . . ?
C4 C3 C2 132.2(4) . . ?
N3 C2 C3 125.0(4) . . ?
N5 C2 N3 110.7(3) . . ?
N5 C2 C3 124.3(4) . . ?
N007 C6 C5 124.4(3) . . ?
N8 C6 N007 111.3(3) . . ?
N8 C6 C5 124.3(3) . . ?
N7 C5 C6 116.8(3) . . ?
N7 C5 C4 112.0(3) . . ?
C4 C5 C6 131.2(4) . . ?
N9 C7 N007 105.6(3) . . ?
N11 C7 N007 126.3(4) . . ?
N11 C7 N9 128.1(4) . . ?
C3 C4 C5 104.0(4) . . ?
C3 C4 H4A 128.0 . . ?
C5 C4 H4A 128.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.460(3) . ?
S1 O3 1.472(3) . ?
S1 O4 1.485(3) . ?
S1 O2 1.472(3) . ?
O5 H5A 0.8502 . ?
O5 H5B 0.85(2) . ?
N007 N10 1.387(4) . ?
N007 C6 1.381(5) . ?
N007 C7 1.361(5) . ?
N3 N2 1.397(4) . ?
N3 C1 1.353(5) . ?
N3 C2 1.374(5) . ?
N7 N6 1.328(5) . ?
N7 C5 1.351(5) . ?
O6 H6A 0.8499 . ?
O6 H6B 0.8503 . ?
N6 H6 0.8800 . ?
N6 C3 1.353(5) . ?
N5 N4 1.378(5) . ?
N5 C2 1.307(5) . ?
N2 H2A 0.8674 . ?
N2 H2B 0.8683 . ?
N4 H4 0.8800 . ?
N4 C1 1.328(5) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C1 1.317(5) . ?
N9 H9 0.8800 . ?
N9 N8 1.381(5) . ?
N9 C7 1.334(5) . ?
N8 C6 1.295(5) . ?
N11 H11A 0.8800 . ?
N11 H11B 0.8800 . ?
N11 C7 1.310(5) . ?
O7 H7A 0.8501 . ?
O7 H7B 0.84(2) . ?
N10 H10A 0.8701 . ?
N10 H10B 0.8709 . ?
C3 C2 1.450(5) . ?
C3 C4 1.374(5) . ?
C6 C5 1.469(5) . ?
C5 C4 1.386(6) . ?
C4 H4A 0.9500 . ?
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
O5 H5A O4 0.85 1.96 2.779(4) 161.6 1_455
O6 H6A O2 0.85 1.98 2.809(4) 165.7 .
O6 H6B O3 0.85 2.07 2.888(4) 160.8 2_645
N6 H6 O2 0.88 1.92 2.785(4) 166.9 3_666
N4 H4 O7 0.88 1.76 2.599(5) 158.8 3_666
N1 H1A O1 0.88 2.06 2.872(4) 152.5 3_676
N9 H9 O5 0.88 1.85 2.724(5) 170.8 1_545
N11 H11A O6 0.88 2.01 2.838(5) 156.0 2_645
N11 H11B O4 0.88 2.06 2.818(5) 143.8 2_645
O7 H7A O3 0.85 1.89 2.736(4) 172.0 2_645
O5 H5B O3 0.85(2) 1.98(2) 2.823(5) 176(5) .
O7 H7B O4 0.84(2) 1.86(2) 2.702(5) 177(5) 1_545
