#------------------------------------------------------------------------------
#$Date: 2022-10-07 04:09:12 +0300 (Fri, 07 Oct 2022) $
#$Revision: 278451 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/17/7061750.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_7061750
loop_
_publ_author_name
'Gribov, Pavel S.'
'Suponitsky, Kyrill Yu.'
'Sheremetev, Aleksei B.'
_publ_section_title
;
 Efficient synthesis of N-(chloromethyl)nitramines via TiCl4-catalyzed
 chlorodeacetoxylation
;
_journal_issue                   36
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              17548
_journal_page_last               17553
_journal_paper_doi               10.1039/D2NJ03521A
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C5 H10 Cl2 N8 O8'
_chemical_formula_sum            'C5 H10 Cl2 N8 O8'
_chemical_formula_weight         381.11
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2021-11-30 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   28.4221(9)
_cell_length_b                   5.9548(2)
_cell_length_c                   25.7279(9)
_cell_measurement_reflns_used    7655
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      2.67
_cell_volume                     4354.4(3)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2015)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0610
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -35
_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            32765
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.072
_diffrn_reflns_theta_min         2.135
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.506
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/5 (Bruker,2014/5)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_description       needle
_exptl_crystal_F_000             2328
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4304
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.192
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0569
_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)+(0.0197P)²+9.9164P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1029
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3615
_reflns_number_total             4304
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj03521a2.cif
_cod_data_source_block           sh449
_cod_depositor_comments
'Adding full bibliography for 7061749--7061750.cif.'
_cod_database_code               7061750
_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.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
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
Cl1 Cl 0.21725(3) 0.75045(16) 0.49228(3) 0.0251(2) Uani 1 1 d . . . . .
Cl2 Cl 0.13160(3) 0.5796(2) 0.91918(3) 0.0373(3) Uani 1 1 d . . . . .
O1 O 0.16628(9) 1.2303(4) 0.53895(9) 0.0257(6) Uani 1 1 d . . . . .
O2 O 0.18340(9) 1.1640(4) 0.62011(9) 0.0223(5) Uani 1 1 d . . . . .
O3 O 0.09748(8) 0.5362(4) 0.60655(9) 0.0218(5) Uani 1 1 d . . . . .
O4 O 0.08467(7) 0.5816(4) 0.68965(9) 0.0201(5) Uani 1 1 d . . . . .
O5 O 0.23785(7) 0.5610(4) 0.69720(8) 0.0155(5) Uani 1 1 d . . . . .
O6 O 0.23093(8) 0.4167(4) 0.77487(8) 0.0183(5) Uani 1 1 d . . . . .
O7 O 0.15374(9) 1.0522(4) 0.80412(9) 0.0241(6) Uani 1 1 d . . . . .
O8 O 0.19010(11) 1.0424(4) 0.87877(10) 0.0401(7) Uani 1 1 d . . . . .
N1 N 0.16063(9) 0.8804(4) 0.56986(10) 0.0133(6) Uani 1 1 d . . . . .
N2 N 0.17113(9) 1.1070(4) 0.57649(10) 0.0169(6) Uani 1 1 d . . . . .
N3 N 0.15033(8) 0.7113(4) 0.65485(9) 0.0116(5) Uani 1 1 d . . . . .
N4 N 0.10842(9) 0.6035(4) 0.65004(10) 0.0150(6) Uani 1 1 d . . . . .
N5 N 0.17446(8) 0.6375(4) 0.74370(10) 0.0117(5) Uani 1 1 d . . . . .
N6 N 0.21724(9) 0.5328(4) 0.73847(10) 0.0134(6) Uani 1 1 d . . . . .
N7 N 0.17777(9) 0.7236(4) 0.83542(10) 0.0150(6) Uani 1 1 d . . . . .
N8 N 0.17331(10) 0.9552(5) 0.84012(11) 0.0213(6) Uani 1 1 d . . . . .
C1 C 0.15896(11) 0.8017(5) 0.51723(12) 0.0160(7) Uani 1 1 d . . . . .
H1A H 0.1430 0.9149 0.4952 0.019 Uiso 1 1 calc R U . . .
H1B H 0.1404 0.6611 0.5157 0.019 Uiso 1 1 calc R U . . .
C2 C 0.17977(10) 0.7287(5) 0.60928(11) 0.0126(6) Uani 1 1 d . . . . .
H2A H 0.1837 0.5776 0.5939 0.015 Uiso 1 1 calc R U . . .
H2B H 0.2113 0.7830 0.6198 0.015 Uiso 1 1 calc R U . . .
C3 C 0.16238(10) 0.8067(5) 0.70506(11) 0.0106(6) Uani 1 1 d . . . . .
H3A H 0.1354 0.8958 0.7179 0.013 Uiso 1 1 calc R U . . .
H3B H 0.1894 0.9101 0.7007 0.013 Uiso 1 1 calc R U . . .
C4 C 0.15141(11) 0.6191(5) 0.79337(11) 0.0143(6) Uani 1 1 d . . . . .
H4A H 0.1467 0.4582 0.8016 0.017 Uiso 1 1 calc R U . . .
H4B H 0.1200 0.6904 0.7911 0.017 Uiso 1 1 calc R U . . .
C5 C 0.18550(11) 0.6035(6) 0.88277(12) 0.0206(7) Uani 1 1 d . . . . .
H5A H 0.2093 0.6831 0.9039 0.025 Uiso 1 1 calc R U . . .
H5B H 0.1977 0.4518 0.8748 0.025 Uiso 1 1 calc R U . . .
Cl1' Cl 0.04499(3) 0.76956(15) 0.47470(3) 0.02278(19) Uani 1 1 d . . . . .
O1' O 0.01324(8) 0.2916(4) 0.41549(9) 0.0232(5) Uani 1 1 d . . . . .
O2' O 0.03388(8) 0.3494(4) 0.33482(8) 0.0171(5) Uani 1 1 d . . . . .
O3' O -0.05928(8) 0.9617(4) 0.34523(8) 0.0209(5) Uani 1 1 d . . . . .
O4' O -0.07604(8) 0.8770(4) 0.26487(9) 0.0222(5) Uani 1 1 d . . . . .
N1' N 0.00937(9) 0.6362(4) 0.38274(10) 0.0129(5) Uani 1 1 d . . . . .
N2' N 0.01952(9) 0.4112(4) 0.37776(10) 0.0150(6) Uani 1 1 d . . . . .
N3' N -0.00664(9) 0.7856(4) 0.29656(9) 0.0125(5) Uani 1 1 d . . . . .
N4' N -0.04984(9) 0.8803(4) 0.30298(10) 0.0161(6) Uani 1 1 d . . . . .
C1' C -0.00468(11) 0.7174(6) 0.43268(12) 0.0151(7) Uani 1 1 d . . . . .
H1'A H -0.0256 0.6057 0.4493 0.018 Uiso 1 1 calc R U . . .
H1'B H -0.0227 0.8583 0.4283 0.018 Uiso 1 1 calc R U . . .
C2' C 0.02455(10) 0.7849(5) 0.34090(11) 0.0131(6) Uani 1 1 d . . . . .
H2'A H 0.0270 0.9398 0.3546 0.016 Uiso 1 1 calc R U . . .
H2'B H 0.0563 0.7385 0.3293 0.016 Uiso 1 1 calc R U . . .
C3' C 0.0000 0.6517(7) 0.2500 0.0111(9) Uani 1 2 d S T P . .
H3'A H -0.0270 0.5570 0.2454 0.013 Uiso 1 1 d 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'
Cl Cl 0.1484 0.1585 '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
N2 N1 C1 116.1(2) . . ?
N2 N1 C2 115.7(2) . . ?
C1 N1 C2 117.7(2) . . ?
O1 N2 O2 126.2(3) . . ?
O1 N2 N1 117.5(3) . . ?
O2 N2 N1 116.3(3) . . ?
N4 N3 C2 117.9(2) . . ?
N4 N3 C3 118.2(2) . . ?
C2 N3 C3 123.9(2) . . ?
O3 N4 O4 125.5(3) . . ?
O3 N4 N3 117.3(2) . . ?
O4 N4 N3 117.1(2) . . ?
N6 N5 C4 117.1(2) . . ?
N6 N5 C3 117.1(2) . . ?
C4 N5 C3 123.4(2) . . ?
O5 N6 O6 126.0(2) . . ?
O5 N6 N5 116.5(2) . . ?
O6 N6 N5 117.5(2) . . ?
N8 N7 C5 115.9(3) . . ?
N8 N7 C4 116.2(2) . . ?
C5 N7 C4 119.9(3) . . ?
O8 N8 O7 126.4(3) . . ?
O8 N8 N7 117.2(3) . . ?
O7 N8 N7 116.3(3) . . ?
N1 C1 Cl1 111.2(2) . . ?
N1 C1 H1A 109.4 . . ?
Cl1 C1 H1A 109.4 . . ?
N1 C1 H1B 109.4 . . ?
Cl1 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
N3 C2 N1 113.1(2) . . ?
N3 C2 H2A 109.0 . . ?
N1 C2 H2A 109.0 . . ?
N3 C2 H2B 109.0 . . ?
N1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N3 C3 N5 113.1(2) . . ?
N3 C3 H3A 109.0 . . ?
N5 C3 H3A 109.0 . . ?
N3 C3 H3B 109.0 . . ?
N5 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
N5 C4 N7 113.1(2) . . ?
N5 C4 H4A 109.0 . . ?
N7 C4 H4A 109.0 . . ?
N5 C4 H4B 109.0 . . ?
N7 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
N7 C5 Cl2 110.6(2) . . ?
N7 C5 H5A 109.5 . . ?
Cl2 C5 H5A 109.5 . . ?
N7 C5 H5B 109.5 . . ?
Cl2 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
N2' N1' C1' 118.1(2) . . ?
N2' N1' C2' 117.4(2) . . ?
C1' N1' C2' 122.7(3) . . ?
O1' N2' O2' 126.0(3) . . ?
O1' N2' N1' 117.7(3) . . ?
O2' N2' N1' 116.3(2) . . ?
N4' N3' C2' 117.3(2) . . ?
N4' N3' C3' 116.4(2) . . ?
C2' N3' C3' 124.8(2) . . ?
O3' N4' O4' 125.6(3) . . ?
O3' N4' N3' 118.1(3) . . ?
O4' N4' N3' 116.3(2) . . ?
N1' C1' Cl1' 112.2(2) . . ?
N1' C1' H1'A 109.2 . . ?
Cl1' C1' H1'A 109.2 . . ?
N1' C1' H1'B 109.2 . . ?
Cl1' C1' H1'B 109.2 . . ?
H1'A C1' H1'B 107.9 . . ?
N3' C2' N1' 113.7(2) . . ?
N3' C2' H2'A 108.8 . . ?
N1' C2' H2'A 108.8 . . ?
N3' C2' H2'B 108.8 . . ?
N1' C2' H2'B 108.8 . . ?
H2'A C2' H2'B 107.7 . . ?
N3' C3' N3' 113.4(3) . 3 ?
N3' C3' H3'A 108.7 . . ?
N3' C3' H3'A 109.0 3 . ?
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
Cl1 C1 1.803(3) . ?
Cl2 C5 1.802(3) . ?
O1 N2 1.221(3) . ?
O2 N2 1.223(3) . ?
O3 N4 1.228(3) . ?
O4 N4 1.229(3) . ?
O5 N6 1.224(3) . ?
O6 N6 1.227(3) . ?
O7 N8 1.225(3) . ?
O8 N8 1.219(3) . ?
N1 N2 1.393(3) . ?
N1 C1 1.434(4) . ?
N1 C2 1.463(4) . ?
N3 N4 1.359(3) . ?
N3 C2 1.444(4) . ?
N3 C3 1.452(4) . ?
N5 N6 1.373(3) . ?
N5 C4 1.440(4) . ?
N5 C3 1.457(4) . ?
N7 N8 1.390(4) . ?
N7 C5 1.429(4) . ?
N7 C4 1.456(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
Cl1' C1' 1.805(3) . ?
O1' N2' 1.217(3) . ?
O2' N2' 1.234(3) . ?
O3' N4' 1.220(3) . ?
O4' N4' 1.231(3) . ?
N1' N2' 1.376(3) . ?
N1' C1' 1.430(4) . ?
N1' C2' 1.459(4) . ?
N3' N4' 1.361(3) . ?
N3' C2' 1.445(4) . ?
N3' C3' 1.451(3) . ?
C1' H1'A 0.9900 . ?
C1' H1'B 0.9900 . ?
C2' H2'A 0.9900 . ?
C2' H2'B 0.9900 . ?
C3' N3' 1.451(3) 3 ?
C3' H3'A 0.9600 . ?
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
C1 N1 N2 O1 18.2(4) . . . . ?
C2 N1 N2 O1 162.3(3) . . . . ?
C1 N1 N2 O2 -163.5(3) . . . . ?
C2 N1 N2 O2 -19.3(4) . . . . ?
C2 N3 N4 O3 -3.0(4) . . . . ?
C3 N3 N4 O3 175.5(3) . . . . ?
C2 N3 N4 O4 177.0(3) . . . . ?
C3 N3 N4 O4 -4.5(4) . . . . ?
C4 N5 N6 O5 -175.7(3) . . . . ?
C3 N5 N6 O5 -12.5(4) . . . . ?
C4 N5 N6 O6 5.7(4) . . . . ?
C3 N5 N6 O6 168.9(3) . . . . ?
C5 N7 N8 O8 22.0(4) . . . . ?
C4 N7 N8 O8 170.9(3) . . . . ?
C5 N7 N8 O7 -159.7(3) . . . . ?
C4 N7 N8 O7 -10.8(4) . . . . ?
N2 N1 C1 Cl1 79.8(3) . . . . ?
C2 N1 C1 Cl1 -63.6(3) . . . . ?
N4 N3 C2 N1 69.8(3) . . . . ?
C3 N3 C2 N1 -108.7(3) . . . . ?
N2 N1 C2 N3 84.8(3) . . . . ?
C1 N1 C2 N3 -131.7(3) . . . . ?
N4 N3 C3 N5 72.5(3) . . . . ?
C2 N3 C3 N5 -109.0(3) . . . . ?
N6 N5 C3 N3 73.3(3) . . . . ?
C4 N5 C3 N3 -124.6(3) . . . . ?
N6 N5 C4 N7 63.3(3) . . . . ?
C3 N5 C4 N7 -98.7(3) . . . . ?
N8 N7 C4 N5 80.9(3) . . . . ?
C5 N7 C4 N5 -131.5(3) . . . . ?
N8 N7 C5 Cl2 76.4(3) . . . . ?
C4 N7 C5 Cl2 -71.3(3) . . . . ?
C1' N1' N2' O1' 4.3(4) . . . . ?
C2' N1' N2' O1' 169.5(3) . . . . ?
C1' N1' N2' O2' -176.3(2) . . . . ?
C2' N1' N2' O2' -11.1(4) . . . . ?
C2' N3' N4' O3' 1.2(4) . . . . ?
C3' N3' N4' O3' 168.0(3) . . . . ?
C2' N3' N4' O4' -179.3(3) . . . . ?
C3' N3' N4' O4' -12.5(4) . . . . ?
N2' N1' C1' Cl1' 81.6(3) . . . . ?
C2' N1' C1' Cl1' -82.8(3) . . . . ?
N4' N3' C2' N1' 69.1(3) . . . . ?
C3' N3' C2' N1' -96.4(3) . . . . ?
N2' N1' C2' N3' 81.0(3) . . . . ?
C1' N1' C2' N3' -114.5(3) . . . . ?
N4' N3' C3' N3' 76.9(2) . . . 3 ?
C2' N3' C3' N3' -117.4(3) . . . 3 ?
