#------------------------------------------------------------------------------
#$Date: 2026-03-04 12:42:47 +0100 (Wed 04 de Mar de 2026) $
#$Revision: 304767 $
#$URL: svn://www.crystallography.net/cod/cif/7/72/05/7720543.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_7720543
loop_
_publ_author_name
'Xu, Zeyu'
'Jiang, Xiu'e'
'Wang, Ruihui'
'Fan, Mingren'
'Wang, Yi'
'Zhang, Qinghua'
_publ_section_title
;
 Facile and low-cost construction of laser-ignitable energetic materials.
;
_journal_issue                   3
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1436
_journal_page_last               1444
_journal_paper_doi               10.1039/d5dt02640g
_journal_volume                  55
_journal_year                    2026
_chemical_formula_moiety         '2(Cl O4), C4 H12 N2, 2(H2 O)'
_chemical_formula_sum            'C4 H16 Cl2 N2 O10'
_chemical_formula_weight         323.09
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2025-12-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2025-12-01 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.000(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1870(5)
_cell_length_b                   6.4760(4)
_cell_length_c                   13.3062(10)
_cell_measurement_reflns_used    1970
_cell_measurement_temperature    170.15
_cell_measurement_theta_max      24.41
_cell_measurement_theta_min      3.09
_cell_volume                     615.92(7)
_computing_cell_refinement       'SAINT V8.41 (?, 2016)'
_computing_data_collection       'Bruker SMART APEX II diffractometer'
_computing_data_reduction        'SAINT V8.41 (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.15
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4361
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        24.507
_diffrn_reflns_theta_max         24.507
_diffrn_reflns_theta_min         3.079
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.4824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1043 before and 0.0725 after correction.
The Ratio of minimum to maximum transmission is 0.6474.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         1012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0405
_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)+(0.0366P)²+0.8094P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.1000
_reflns_Friedel_coverage         0.000
_reflns_number_gt                859
_reflns_number_total             1012
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5dt02640g4.cif
_cod_data_source_block           111
_cod_database_code               7720543
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O003(H00G,H00H)
2.b Secondary CH2 refined with riding coordinates:
 N00A(H00A,H00B), C00C(H00C,H00D), C00F(H00E,H00F)
;
_shelx_res_file
;
TITL 111_a.res in Pn New:P21/n
    111.res
    created by SHELXL-2018/3 at 08:54:38 on 01-Dec-2025
CELL 0.71073 7.187 6.476 13.3062 90 96 90
ZERR 2 0.0005 0.0004 0.001 0 0.002 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H Cl N O
UNIT 8 32 4 4 20
EQIV $1 0.5-X,-0.5+Y,0.5-Z
EQIV $2 0.5+X,0.5-Y,-0.5+Z

L.S. 5
PLAN  5
TEMP -103
CONF
HTAB N00A O003_$1
HTAB N00A O003_$2
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\111.hkl">
REM </olex2.extras>

WGHT    0.036600    0.809400
FVAR       0.87060
CL01  3    0.556083    0.395741    0.341542    11.00000    0.01819    0.02619 =
         0.01782    0.00135    0.00178   -0.00106
O004  5    0.678525    0.472797    0.425106    11.00000    0.02529    0.04000 =
         0.02043   -0.00536   -0.00196   -0.00496
O007  5    0.666299    0.332635    0.262340    11.00000    0.02319    0.04194 =
         0.01906   -0.00558    0.00810   -0.00165
O00E  5    0.454982    0.220649    0.373552    11.00000    0.03525    0.04205 =
         0.04168   -0.00075    0.01245   -0.01839
O00G  5    0.425629    0.552381    0.304578    11.00000    0.03942    0.05517 =
         0.03952    0.01068   -0.00055    0.02360
N00A  4    0.526659    0.296141    0.039405    11.00000    0.02895    0.01646 =
         0.01851    0.00091    0.00132    0.00162
AFIX  23
H00A  2    0.550154    0.207482    0.092267    11.00000   -1.20000
H00B  2    0.512651    0.220325   -0.018473    11.00000   -1.20000
AFIX   0
C00C  1    0.349975    0.411377    0.050259    11.00000    0.02338    0.02327 =
         0.01725   -0.00069    0.00527    0.00009
AFIX  23
H00C  2    0.361778    0.487915    0.115018    11.00000   -1.20000
H00D  2    0.244587    0.313055    0.050708    11.00000   -1.20000
AFIX   0
C00F  1    0.688207    0.439671    0.036452    11.00000    0.02032    0.02309 =
         0.02280    0.00151    0.00188    0.00121
AFIX  23
H00E  2    0.803010    0.359688    0.028193    11.00000   -1.20000
H00F  2    0.708441    0.517047    0.100834    11.00000   -1.20000
AFIX   6

O003  5    0.047064    0.426491    0.354443    11.00000    0.01763    0.02809 =
         0.02057   -0.00099    0.00288   -0.00007
H00G  2   -0.033489    0.388530    0.304514    11.00000   -1.50000
H00H  2    0.154462    0.422994    0.329811    11.00000   -1.50000
AFIX   0
HKLF 4




REM  111_a.res in Pn New:P21/n
REM wR2 = 0.1000, GooF = S = 1.074, Restrained GooF = 1.074 for all data
REM R1 = 0.0405 for 859 Fo > 4sig(Fo) and 0.0531 for all 1012 data
REM 85 parameters refined using 0 restraints

END

WGHT      0.0366      0.8094

REM Highest difference peak  0.346,  deepest hole -0.452,  1-sigma level  0.076
Q1    1   0.5465  0.5739  0.3185  11.00000  0.05    0.35
Q2    1   0.4684  0.6785  0.3056  11.00000  0.05    0.31
Q3    1   0.3588  0.2893  0.3410  11.00000  0.05    0.28
Q4    1   0.7008  0.4684  0.2839  11.00000  0.05    0.26
Q5    1   0.6022  0.2016  0.4379  11.00000  0.05    0.26
;
_shelx_res_checksum              52895
_olex2_submission_special_instructions 'No special instructions were received'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl01 Cl 0.55608(9) 0.39574(11) 0.34154(5) 0.0207(3) Uani 1 1 d . . . . .
O004 O 0.6785(3) 0.4728(4) 0.42511(16) 0.0289(6) Uani 1 1 d . . . . .
O007 O 0.6663(3) 0.3326(3) 0.26234(16) 0.0276(5) Uani 1 1 d . . . . .
O00E O 0.4550(3) 0.2206(4) 0.37355(18) 0.0391(6) Uani 1 1 d . . . . .
O00G O 0.4256(3) 0.5524(4) 0.30458(19) 0.0450(7) Uani 1 1 d . . . . .
N00A N 0.5267(3) 0.2961(4) 0.03941(18) 0.0214(6) Uani 1 1 d . . . . .
H00A H 0.550154 0.207482 0.092267 0.026 Uiso 1 1 calc R U . . .
H00B H 0.512651 0.220325 -0.018473 0.026 Uiso 1 1 calc R U . . .
C00C C 0.3500(4) 0.4114(4) 0.0503(2) 0.0211(7) Uani 1 1 d . . . . .
H00C H 0.361778 0.487915 0.115018 0.025 Uiso 1 1 calc R U . . .
H00D H 0.244587 0.313055 0.050708 0.025 Uiso 1 1 calc R U . . .
C00F C 0.6882(4) 0.4397(4) 0.0365(2) 0.0221(7) Uani 1 1 d . . . . .
H00E H 0.803010 0.359688 0.028193 0.027 Uiso 1 1 calc R U . . .
H00F H 0.708441 0.517047 0.100834 0.027 Uiso 1 1 calc R U . . .
O003 O 0.0471(3) 0.4265(3) 0.35444(15) 0.0220(5) Uani 1 1 d G . . . .
H00G H -0.033489 0.388530 0.304514 0.033 Uiso 1 1 d G U . . .
H00H H 0.154462 0.422994 0.329811 0.033 Uiso 1 1 d G U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl01 0.0182(4) 0.0262(4) 0.0178(4) 0.0014(3) 0.0018(3) -0.0011(3)
O004 0.0253(12) 0.0400(13) 0.0204(12) -0.0054(10) -0.0020(10) -0.0050(10)
O007 0.0232(11) 0.0419(13) 0.0191(11) -0.0056(10) 0.0081(10) -0.0017(9)
O00E 0.0352(14) 0.0421(14) 0.0417(14) -0.0008(11) 0.0124(12) -0.0184(11)
O00G 0.0394(14) 0.0552(16) 0.0395(15) 0.0107(12) -0.0006(13) 0.0236(12)
N00A 0.0290(14) 0.0165(12) 0.0185(13) 0.0009(10) 0.0013(11) 0.0016(10)
C00C 0.0234(16) 0.0233(16) 0.0172(16) -0.0007(12) 0.0053(13) 0.0001(12)
C00F 0.0203(15) 0.0231(16) 0.0228(16) 0.0015(12) 0.0019(14) 0.0012(12)
O003 0.0176(11) 0.0281(12) 0.0206(12) -0.0010(9) 0.0029(9) -0.0001(9)
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'
Cl Cl 0.1484 0.1585 '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'
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
O004 Cl01 O007 109.02(13) . . ?
O004 Cl01 O00E 109.49(14) . . ?
O00E Cl01 O007 109.07(14) . . ?
O00G Cl01 O004 110.26(15) . . ?
O00G Cl01 O007 109.84(14) . . ?
O00G Cl01 O00E 109.13(15) . . ?
H00A N00A H00B 108.0 . . ?
C00C N00A H00A 109.4 . . ?
C00C N00A H00B 109.4 . . ?
C00F N00A H00A 109.4 . . ?
C00F N00A H00B 109.4 . . ?
C00F N00A C00C 111.3(2) . . ?
N00A C00C H00C 109.8 . . ?
N00A C00C H00D 109.8 . . ?
N00A C00C C00F 109.5(2) . 3_665 ?
H00C C00C H00D 108.2 . . ?
C00F C00C H00C 109.8 3_665 . ?
C00F C00C H00D 109.8 3_665 . ?
N00A C00F C00C 109.8(2) . 3_665 ?
N00A C00F H00E 109.7 . . ?
N00A C00F H00F 109.7 . . ?
C00C C00F H00E 109.7 3_665 . ?
C00C C00F H00F 109.7 3_665 . ?
H00E C00F H00F 108.2 . . ?
H00G O003 H00H 104.5 . . ?
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
Cl01 O004 1.434(2) . ?
Cl01 O007 1.442(2) . ?
Cl01 O00E 1.435(2) . ?
Cl01 O00G 1.433(2) . ?
N00A H00A 0.9100 . ?
N00A H00B 0.9100 . ?
N00A C00C 1.493(4) . ?
N00A C00F 1.491(4) . ?
C00C H00C 0.9900 . ?
C00C H00D 0.9900 . ?
C00C C00F 1.507(4) 3_665 ?
C00F H00E 0.9900 . ?
C00F H00F 0.9900 . ?
O003 H00G 0.8698 . ?
O003 H00H 0.8698 . ?
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
_geom_hbond_publ_flag
N00A H00A O003 0.91 2.10 2.857(3) 140.1 2_545 yes
N00A H00B O003 0.91 1.98 2.869(3) 166.0 4_665 yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C00C N00A C00F C00C -58.5(3) . . . 3_665 ?
C00F N00A C00C C00F 58.3(3) . . . 3_665 ?
