#------------------------------------------------------------------------------
#$Date: 2026-03-04 12:42:47 +0100 (Wed 04 de Mar de 2026) $
#$Revision: 304767 $
#$URL: svn://www.crystallography.net/cod/cif/7/72/05/7720540.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_7720540
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         'C4 H10 N O, Cl O4'
_chemical_formula_sum            'C4 H10 Cl N O5'
_chemical_formula_weight         187.58
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.284(6)
_cell_length_b                   9.770(7)
_cell_length_c                   9.568(7)
_cell_measurement_reflns_used    1907
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      25.30
_cell_measurement_theta_min      2.98
_cell_volume                     774.4(10)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker SMART APEX II diffractometer'
_computing_data_reduction        'SAINT V8.40B (?, 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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_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  0.0526
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5938
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.980
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.471
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1274 before and 0.0634 after correction.
The Ratio of minimum to maximum transmission is 0.6993.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.812
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         942
_refine_ls_number_restraints     81
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0743
_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)+(0.1050P)²+1.1069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1879
_refine_ls_wR_factor_ref         0.2119
_reflns_Friedel_coverage         0.000
_reflns_number_gt                725
_reflns_number_total             942
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5dt02640g4.cif
_cod_data_source_block           1
_cod_original_cell_volume        774.4(9)
_cod_database_code               7720540
_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
2. Restrained distances
 Cl2-O3 = Cl2-O4 = Cl2-O5 = Cl2-O6
 1.5 with sigma of 0.02
 Cl2-O3 \\sim Cl2-O4 \\sim Cl2-O5 \\sim Cl2-O6
 with sigma of 0.02
 O3-O5 \\sim O4-O6 \\sim O3-O6 \\sim O4-O5 \\sim O3-O4 \\sim O5-O6
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Cl2 \\sim O3 \\sim O4 \\sim O5 \\sim O6: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
Uanis(O5) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
4. Rigid body (RIGU) restrains
 Cl2, O3, O4, O5, O6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: Cl2(0.5) O3(0.5) O4(0.5) O5(0.5) O6(0.5)
6.a Secondary CH2 refined with riding coordinates:
 N003(H00A,H00B), C005(H00C,H00D), C006(H00E,H00F)
;
_shelx_res_file
;
TITL 1_a.res in Pnma
    1.res
    created by SHELXL-2018/3 at 09:09:49 on 01-Dec-2025
REM Old TITL 1_a.res in Pnma
REM SHELXT solution in Pnma
REM R1 0.213, Rweak 0.075, Alpha 0.031, Orientation as input
REM Formula found by SHELXT: C8 Cl O3
CELL 0.71073 8.2837 9.7697 9.5683 90 90 90
ZERR 4 0.0058 0.0065 0.0072 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,-Z
SYMM 0.5+X,0.5-Y,0.5-Z
SFAC C H Cl N O
UNIT 16 40 4 4 20
EQIV $1 0.5+X,1.5-Y,1.5-Z
EQIV $2 0.5-X,1-Y,-0.5+Z
EQIV $3 0.5-X,0.5+Y,-0.5+Z
DFIX 1.5 Cl2 O3 Cl2 O4 Cl2 O5 Cl2 O6
SADI Cl2 O3 Cl2 O4 Cl2 O5 Cl2 O6
SADI 0.04 O3 O5 O4 O6 O3 O6 O4 O5 O3 O4 O5 O6
SIMU Cl2 O3 O4 O5 O6
RIGU Cl2 O3 O4 O5 O6
ISOR 0.003 0.006 O5

L.S. 20
PLAN  5
TEMP 19.85
CONF
HTAB N003 O002_$1
HTAB N003 O4_$2
HTAB N003 O4_$3
list 4
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\1.hkl">
REM </olex2.extras>

WGHT    0.105000    1.106900
FVAR       1.62776
O002  5    0.020609    0.750000    0.756112    10.50000    0.03915    0.06615 =
         0.04701    0.00000    0.01438    0.00000
N003  4    0.258254    0.750000    0.545179    10.50000    0.03320    0.06045 =
         0.02751    0.00000    0.00082    0.00000
AFIX  23
H00A  2    0.284194    0.750000    0.454915    10.50000   -1.20000
H00B  2    0.349365    0.749999    0.594474    10.50000   -1.20000
AFIX   0
C005  1    0.165118    0.626010    0.577775    11.00000    0.05136    0.04232 =
         0.05226   -0.00327   -0.00059    0.00442
AFIX  23
H00C  2    0.230556    0.545335    0.560973    11.00000   -1.20000
H00D  2    0.070401    0.621084    0.518381    11.00000   -1.20000
AFIX   0
C006  1    0.114680    0.631296    0.729728    11.00000    0.05495    0.05378 =
         0.05454    0.01476    0.00544   -0.00370
AFIX  23
H00E  2    0.052346    0.550254    0.752478    11.00000   -1.20000
H00F  2    0.209917    0.632306    0.788704    11.00000   -1.20000
AFIX   0

PART -1
CL2   3    0.340284    0.263810    0.637791    10.50000    0.04414    0.05001 =
         0.05241   -0.00234   -0.01269    0.00356
O3    5    0.446036    0.360221    0.573439    10.50000    0.04763    0.08581 =
         0.06583   -0.01413    0.01977   -0.01479
O4    5    0.304757    0.330772    0.763522    10.50000    0.12451    0.14946 =
         0.03439   -0.02244    0.01745   -0.02234
O5    5    0.427645    0.142060    0.655266    10.50000    0.14644    0.11544 =
         0.16409    0.00583   -0.02570    0.02309
O6    5    0.202912    0.243342    0.553985    10.50000    0.05132    0.12155 =
         0.07728   -0.00127   -0.02156   -0.03150
HKLF 4




REM  1_a.res in Pnma
REM wR2 = 0.2119, GooF = S = 1.073, Restrained GooF = 1.164 for all data
REM R1 = 0.0743 for 725 Fo > 4sig(Fo) and 0.0961 for all 942 data
REM 76 parameters refined using 81 restraints

END

WGHT      0.1050      1.1069

REM Highest difference peak  0.812,  deepest hole -0.477,  1-sigma level  0.080
Q1    1   0.3386  0.2500  0.7715  10.50000  0.05    0.81
Q2    1   0.4822  0.2500  0.5830  10.50000  0.05    0.67
Q3    1   0.3426  0.3694  0.7264  11.00000  0.05    0.58
Q4    1   0.2347  0.3352  0.7398  11.00000  0.05    0.39
Q5    1   0.3802  0.3556  0.5490  11.00000  0.05    0.27
;
_shelx_res_checksum              95098
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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
O002 O 0.0206(4) 0.750000 0.7561(4) 0.0508(9) Uani 1 2 d S T P . .
N003 N 0.2583(4) 0.750000 0.5452(4) 0.0404(9) Uani 1 2 d S T P . .
H00A H 0.284194 0.750000 0.454915 0.048 Uiso 1 2 calc R U P . .
H00B H 0.349365 0.749999 0.594474 0.048 Uiso 1 2 calc R U P . .
C005 C 0.1651(4) 0.6260(4) 0.5778(4) 0.0486(9) Uani 1 1 d . . . . .
H00C H 0.230556 0.545335 0.560973 0.058 Uiso 1 1 calc R U . . .
H00D H 0.070401 0.621084 0.518381 0.058 Uiso 1 1 calc R U . . .
C006 C 0.1147(5) 0.6313(4) 0.7297(4) 0.0544(10) Uani 1 1 d . . . . .
H00E H 0.052346 0.550254 0.752478 0.065 Uiso 1 1 calc R U . . .
H00F H 0.209917 0.632306 0.788704 0.065 Uiso 1 1 calc R U . . .
Cl2 Cl 0.34028(19) 0.2638(12) 0.63779(17) 0.0489(15) Uani 0.5 1 d D U P A -1
O3 O 0.4460(7) 0.3602(7) 0.5734(7) 0.0664(17) Uani 0.5 1 d D U P A -1
O4 O 0.3048(10) 0.3308(9) 0.7635(6) 0.103(3) Uani 0.5 1 d D U P A -1
O5 O 0.4276(17) 0.1421(12) 0.6553(15) 0.142(4) Uani 0.5 1 d D U P A -1
O6 O 0.2029(6) 0.243(3) 0.5540(5) 0.083(2) Uani 0.5 1 d D U P A -1
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
O002 0.0391(17) 0.066(2) 0.0470(18) 0.000 0.0144(14) 0.000
N003 0.0332(19) 0.060(2) 0.0275(16) 0.000 0.0008(14) 0.000
C005 0.051(2) 0.0423(19) 0.052(2) -0.0033(15) -0.0006(15) 0.0044(16)
C006 0.055(2) 0.054(2) 0.055(2) 0.0148(17) 0.0054(17) -0.0037(18)
Cl2 0.0441(8) 0.050(4) 0.0524(8) -0.0023(13) -0.0127(5) 0.0036(14)
O3 0.048(3) 0.086(4) 0.066(4) -0.014(3) 0.020(3) -0.015(3)
O4 0.125(6) 0.149(6) 0.034(3) -0.022(4) 0.017(3) -0.022(5)
O5 0.146(6) 0.115(5) 0.164(7) 0.006(5) -0.026(5) 0.023(5)
O6 0.051(3) 0.122(6) 0.077(3) -0.001(10) -0.022(2) -0.032(8)
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
C006 O002 C006 109.5(4) 7_575 . ?
H00A N003 H00B 108.0 . . ?
C005 N003 H00A 109.4 . . ?
C005 N003 H00A 109.4 7_575 . ?
C005 N003 H00B 109.4 7_575 . ?
C005 N003 H00B 109.4 . . ?
C005 N003 C005 111.0(4) . 7_575 ?
N003 C005 H00C 109.9 . . ?
N003 C005 H00D 109.9 . . ?
N003 C005 C006 108.7(3) . . ?
H00C C005 H00D 108.3 . . ?
C006 C005 H00C 109.9 . . ?
C006 C005 H00D 109.9 . . ?
O002 C006 C005 110.5(3) . . ?
O002 C006 H00E 109.6 . . ?
O002 C006 H00F 109.6 . . ?
C005 C006 H00E 109.6 . . ?
C005 C006 H00F 109.6 . . ?
H00E C006 H00F 108.1 . . ?
O4 Cl2 O3 101.0(7) . . ?
O4 Cl2 O5 113.7(7) . . ?
O4 Cl2 O6 112.7(7) . . ?
O5 Cl2 O3 107.1(6) . . ?
O5 Cl2 O6 111.4(13) . . ?
O6 Cl2 O3 110.2(8) . . ?
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
O002 C006 1.420(5) 7_575 ?
O002 C006 1.420(4) . ?
N003 H00A 0.8900 . ?
N003 H00B 0.8900 . ?
N003 C005 1.470(4) 7_575 ?
N003 C005 1.470(4) . ?
C005 H00C 0.9700 . ?
C005 H00D 0.9700 . ?
C005 C006 1.514(6) . ?
C006 H00E 0.9700 . ?
C006 H00F 0.9700 . ?
Cl2 O3 1.426(8) . ?
Cl2 O4 1.401(7) . ?
Cl2 O5 1.402(10) . ?
Cl2 O6 1.406(5) . ?
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
N003 H00A O4 0.89 2.13 2.856(8) 138.8 8_665 yes
N003 H00A O4 0.89 2.13 2.856(8) 138.8 2_564 yes
N003 H00B O002 0.89 2.01 2.888(5) 166.8 4_566 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
N003 C005 C006 O002 58.8(4) . . . . ?
C005 N003 C005 C006 -56.2(5) 7_575 . . . ?
C006 O002 C006 C005 -62.2(5) 7_575 . . . ?
