#------------------------------------------------------------------------------
#$Date: 2022-10-07 03:09:12 +0200 (Fri 07 de Oct de 2022) $
#$Revision: 278451 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/17/7061749.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_7061749
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         'C4 H8 Cl2 N4 O4'
_chemical_formula_sum            'C4 H8 Cl2 N4 O4'
_chemical_formula_weight         247.04
_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   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                 112.7940(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.8212(4)
_cell_length_b                   11.9073(9)
_cell_length_c                   7.3664(5)
_cell_measurement_reflns_used    3229
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.79
_cell_measurement_theta_min      3.42
_cell_volume                     470.72(6)
_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 1.000
_diffrn_measured_fraction_theta_max 0.996
_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  0.0252
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5559
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.844
_diffrn_reflns_theta_min         3.422
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/5 (Bruker,2014/5)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_description       needle
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         1209
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0248
_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)+(0.0247P)²+0.2392P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0599
_refine_ls_wR_factor_ref         0.0615
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1115
_reflns_number_total             1209
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj03521a2.cif
_cod_data_source_block           sh434
_cod_depositor_comments
'Adding full bibliography for 7061749--7061750.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7061749
_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
_shelx_res_file
;
TITL sh434 in P2(1)/c
CELL 0.71073   5.8212  11.9073   7.3664  90.000 112.794  90.000
ZERR    2.00   0.0004   0.0009   0.0005   0.000   0.001   0.000
LATT  1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C H N O CL
UNIT 8 16 8 8 4
TEMP -173.000

ACTA
CONF
HTAB

L.S. 4
BOND $H
FMAP 2
PLAN 10

WGHT    0.024700    0.239200
FVAR       1.03414
CL1   5    0.802160    0.410199    0.583020    11.00000    0.02186    0.03109 =
         0.01377    0.00144    0.00628    0.00126
O1    4    0.328759    0.261641    0.290104    11.00000    0.03115    0.02162 =
         0.03488    0.01012    0.01484   -0.00417
O2    4    0.120103    0.385888    0.069703    11.00000    0.01831    0.02797 =
         0.02090    0.00116    0.00572   -0.00002
N1    3    0.534821    0.390608    0.192527    11.00000    0.01792    0.01560 =
         0.01496    0.00245    0.00663   -0.00220
N2    3    0.314668    0.343130    0.184474    11.00000    0.02077    0.01668 =
         0.01844   -0.00057    0.00942   -0.00298
C1    1    0.757716    0.351403    0.344025    11.00000    0.02046    0.02025 =
         0.01710    0.00128    0.00919    0.00414
AFIX  23
H1A   2    0.901761    0.371748    0.310874    11.00000   -1.20000
H1B   2    0.751757    0.268484    0.351034    11.00000   -1.20000
AFIX   0
C2    1    0.519365    0.503519    0.108519    11.00000    0.02336    0.01292 =
         0.01295    0.00031    0.00829   -0.00258
AFIX  23
H2A   2    0.674864    0.545230    0.182250    11.00000   -1.20000
H2B   2    0.378988    0.544975    0.121334    11.00000   -1.20000

AFIX   0
HKLF 4

REM  sh434 in P2(1)/c
REM R1 =  0.0248 for    1115 Fo > 4sig(Fo)  and  0.0272 for all    1209 data
REM     64 parameters refined using      0 restraints

END

WGHT      0.0247      0.2392

REM Instructions for potential hydrogen bonds
EQIV $1 x+1, y, z
HTAB C1 O2_$1
EQIV $2 -x+1, y+1/2, -z+1/2
HTAB C2 O1_$2
EQIV $3 -x+1, -y+1, -z+1
HTAB C2 Cl1_$3

REM Highest difference peak  0.415,  deepest hole -0.239,  1-sigma level  0.052
Q1    1   0.5000  0.5000  0.0000  10.50000  0.05    0.42
Q2    1   0.5184  0.4460  0.1511  11.00000  0.05    0.26
Q3    1   0.6386  0.3778  0.2727  11.00000  0.05    0.22
Q4    1   0.4469  0.3742  0.2027  11.00000  0.05    0.22
Q5    1   0.7851  0.3776  0.4522  11.00000  0.05    0.20
Q6    1   0.3198  0.3143  0.2785  11.00000  0.05    0.18
Q7    1   0.4404  0.2416  0.3305  11.00000  0.05    0.18
Q8    1   0.2650  0.2573  0.1973  11.00000  0.05    0.18
Q9    1   0.5137  0.5550  0.1555  11.00000  0.05    0.17
Q10   1   0.7886  0.4973  0.5736  11.00000  0.05    0.17
;
_shelx_res_checksum              71968
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
Cl1 Cl 0.80216(5) 0.41020(3) 0.58302(4) 0.02243(10) Uani 1 1 d . . . . .
O1 O 0.32876(19) 0.26164(8) 0.29010(15) 0.0286(2) Uani 1 1 d . . . . .
O2 O 0.12010(16) 0.38589(8) 0.06970(13) 0.0230(2) Uani 1 1 d . . . . .
N1 N 0.53482(18) 0.39061(8) 0.19253(14) 0.0161(2) Uani 1 1 d . . . . .
N2 N 0.31467(19) 0.34313(8) 0.18447(15) 0.0181(2) Uani 1 1 d . . . . .
C1 C 0.7577(2) 0.35140(10) 0.34403(17) 0.0187(2) Uani 1 1 d . . . . .
H1A H 0.9018 0.3717 0.3109 0.022 Uiso 1 1 calc R U . . .
H1B H 0.7518 0.2685 0.3510 0.022 Uiso 1 1 calc R U . . .
C2 C 0.5194(2) 0.50352(9) 0.10852(16) 0.0160(2) Uani 1 1 d . . . . .
H2A H 0.6749 0.5452 0.1823 0.019 Uiso 1 1 calc R U . . .
H2B H 0.3790 0.5450 0.1213 0.019 Uiso 1 1 calc R 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
Cl1 0.02186(16) 0.03109(18) 0.01377(15) 0.00144(11) 0.00628(11) 0.00126(11)
O1 0.0312(5) 0.0216(5) 0.0349(5) 0.0101(4) 0.0148(4) -0.0042(4)
O2 0.0183(4) 0.0280(5) 0.0209(4) 0.0012(4) 0.0057(3) 0.0000(3)
N1 0.0179(5) 0.0156(5) 0.0150(5) 0.0024(4) 0.0066(4) -0.0022(4)
N2 0.0208(5) 0.0167(5) 0.0184(5) -0.0006(4) 0.0094(4) -0.0030(4)
C1 0.0205(6) 0.0203(6) 0.0171(5) 0.0013(4) 0.0092(5) 0.0041(4)
C2 0.0234(5) 0.0129(5) 0.0129(5) 0.0003(4) 0.0083(4) -0.0026(4)
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 116.65(9) . . ?
N2 N1 C2 116.91(9) . . ?
C1 N1 C2 121.29(10) . . ?
O1 N2 O2 125.50(10) . . ?
O1 N2 N1 117.63(10) . . ?
O2 N2 N1 116.87(10) . . ?
N1 C1 Cl1 112.19(8) . . ?
N1 C1 H1A 109.2 . . ?
Cl1 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
Cl1 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
N1 C2 C2 110.54(11) . 3_665 ?
N1 C2 H2A 109.5 . . ?
C2 C2 H2A 109.5 3_665 . ?
N1 C2 H2B 109.5 . . ?
C2 C2 H2B 109.5 3_665 . ?
H2A C2 H2B 108.1 . . ?
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 1.8176(12) . ?
O1 N2 1.2265(14) . ?
O2 N2 1.2308(14) . ?
N1 N2 1.3808(14) . ?
N1 C1 1.4230(15) . ?
N1 C2 1.4682(14) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C2 1.528(2) 3_665 ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
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 -9.20(15) . . . . ?
C2 N1 N2 O1 -164.18(10) . . . . ?
C1 N1 N2 O2 171.51(10) . . . . ?
C2 N1 N2 O2 16.52(14) . . . . ?
N2 N1 C1 Cl1 -76.83(12) . . . . ?
C2 N1 C1 Cl1 76.99(12) . . . . ?
N2 N1 C2 C2 -91.07(14) . . . 3_665 ?
C1 N1 C2 C2 115.18(14) . . . 3_665 ?
