#------------------------------------------------------------------------------
#$Date: 2023-07-06 21:17:53 +0300 (Thu, 06 Jul 2023) $
#$Revision: 285050 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/27/2022767.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022767
loop_
_publ_author_name
'Honda, Takafumi'
'Ito, Michiko'
'Yamaguchi, Kazuo'
'Kasuga, Noriko Chikaraishi'
'Sato, Hiroyasu'
_publ_section_title
;
 Synthesis and structure of photodegradable
 1-(4,5-dimeth-oxy-2,3-di-nitro-phen-yl)-2-methyl-propyl
 N-butyl-carbamate.
;
_journal_coeditor_code           EX2069
_journal_issue                   'Pt 6'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              549
_journal_page_last               551
_journal_paper_doi               10.1107/S2056989023004103
_journal_volume                  79
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_compound_source        'local laboratory'
_chemical_formula_iupac          'C17 H25 N3 O8'
_chemical_formula_moiety         'C17 H25 N3 O8'
_chemical_formula_sum            'C17 H25 N3 O8'
_chemical_formula_weight         399.40
_chemical_melting_point_gt       380.1
_chemical_melting_point_lt       274.2
_chemical_name_systematic
;
1-(4,5-Dimethoxy-2,3-dinitrophenyl)-2-methylpropyl N-butylcarbamate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.616(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9490(4)
_cell_length_b                   19.9223(8)
_cell_length_c                   10.2378(4)
_cell_measurement_reflns_used    10281
_cell_measurement_temperature    120
_cell_measurement_theta_max      31.2100
_cell_measurement_theta_min      3.3520
_cell_volume                     2011.30(14)
_computing_cell_refinement
;
CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)
;
_computing_data_collection
;
CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)
;
_computing_molecular_graphics
;
Olex2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
ShelXT (Sheldrick, 2015aa)
;
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku VariMax SaturnCCD724'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18806
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.253
_diffrn_reflns_theta_min         3.374
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2018)
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.185
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         5927
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0448
_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)+(0.0400P)²+0.1525P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0939
_reflns_number_gt                4720
_reflns_number_total             5927
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ex2069sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2022767.cif.'
_cod_database_code               2022767
_cod_database_fobs_code          2022767
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.13662(19) 0.40830(14) 0.6373(2) 0.0649(7) Uani d 1 . .
O O2 0.18717(19) 0.32139(11) 0.5256(2) 0.0512(5) Uani d 1 . .
O O3 0.2890(2) 0.41867(10) 0.9547(2) 0.0502(5) Uani d 1 . .
O O4 0.2377(2) 0.32211(10) 0.8644(2) 0.0483(5) Uani d 1 . .
O O5 0.57340(17) 0.39172(8) 0.96576(16) 0.0313(4) Uani d 1 . .
O O6 0.75485(16) 0.42284(9) 0.80062(16) 0.0341(4) Uani d 1 . .
O O7 0.48515(15) 0.43395(7) 0.34698(15) 0.0246(3) Uani d 1 . .
O O8 0.30610(16) 0.50552(8) 0.34710(17) 0.0349(4) Uani d 1 . .
N N1 0.2168(2) 0.36864(14) 0.5995(2) 0.0403(6) Uani d 1 . .
N N2 0.3014(2) 0.37462(11) 0.8748(2) 0.0346(5) Uani d 1 . .
N N3 0.5126(2) 0.54139(9) 0.30272(19) 0.0248(4) Uani d 1 . .
C C1 0.4522(2) 0.38928(11) 0.5581(2) 0.0242(5) Uani d 1 . .
C C2 0.3608(2) 0.38015(11) 0.6472(2) 0.0266(5) Uani d 1 . .
C C3 0.4010(2) 0.38545(11) 0.7824(2) 0.0270(5) Uani d 1 . .
C C4 0.5334(2) 0.39790(11) 0.8338(2) 0.0260(5) Uani d 1 . .
C C5 0.6271(2) 0.40978(11) 0.7437(2) 0.0255(5) Uani d 1 . .
C C6 0.5857(2) 0.40607(11) 0.6096(2) 0.0249(5) Uani d 1 . .
C C7 0.4121(2) 0.38328(11) 0.4104(2) 0.0262(5) Uani d 1 . .
C C8 0.4431(3) 0.31488(12) 0.3535(2) 0.0309(5) Uani d 1 . .
C C9 0.5937(3) 0.29733(13) 0.3712(3) 0.0413(6) Uani d 1 . .
C C10 0.3836(3) 0.31118(14) 0.2093(3) 0.0426(7) Uani d 1 . .
C C11 0.4244(2) 0.49560(11) 0.3336(2) 0.0233(4) Uani d 1 . .
C C12 0.4751(2) 0.61096(11) 0.2740(2) 0.0288(5) Uani d 1 . .
C C13 0.4652(2) 0.62909(11) 0.1295(2) 0.0289(5) Uani d 1 . .
C C14 0.4296(3) 0.70286(12) 0.1055(3) 0.0374(6) Uani d 1 . .
C C15 0.4166(3) 0.72204(14) -0.0381(3) 0.0421(7) Uani d 1 . .
C C16 0.6073(3) 0.45403(14) 1.0351(3) 0.0446(7) Uani d 1 . .
C C17 0.8593(2) 0.42724(15) 0.7164(3) 0.0412(7) Uani d 1 . .
H H3 0.588(3) 0.5291(12) 0.310(3) 0.026(7) Uiso d 1 . .
H H6 0.648082 0.414974 0.551752 0.030 Uiso calc 1 . .
H H7 0.314682 0.392050 0.389922 0.031 Uiso calc 1 . .
H H8 0.397129 0.280852 0.400680 0.037 Uiso calc 1 . .
H H9A 0.642527 0.331190 0.330187 0.062 Uiso calc 1 . .
H H9B 0.606179 0.254638 0.331034 0.062 Uiso calc 1 . .
H H9C 0.627043 0.295128 0.463472 0.062 Uiso calc 1 . .
H H10A 0.288238 0.320714 0.200686 0.064 Uiso calc 1 . .
H H10B 0.397234 0.266968 0.176167 0.064 Uiso calc 1 . .
H H10C 0.427650 0.343506 0.159920 0.064 Uiso calc 1 . .
H H12A 0.541687 0.639913 0.323654 0.035 Uiso calc 1 . .
H H12B 0.388247 0.619657 0.303969 0.035 Uiso calc 1 . .
H H13A 0.396452 0.601434 0.079559 0.035 Uiso calc 1 . .
H H13B 0.551210 0.619674 0.098363 0.035 Uiso calc 1 . .
H H14A 0.344649 0.712310 0.138677 0.045 Uiso calc 1 . .
H H14B 0.499305 0.730341 0.154638 0.045 Uiso calc 1 . .
H H15A 0.500225 0.712690 -0.071672 0.063 Uiso calc 1 . .
H H15B 0.396447 0.769065 -0.047350 0.063 Uiso calc 1 . .
H H15C 0.344706 0.696579 -0.086689 0.063 Uiso calc 1 . .
H H16A 0.675426 0.477282 0.994558 0.067 Uiso calc 1 . .
H H16B 0.641171 0.444566 1.125445 0.067 Uiso calc 1 . .
H H16C 0.527663 0.481566 1.031391 0.067 Uiso calc 1 . .
H H17A 0.839687 0.463759 0.655666 0.062 Uiso calc 1 . .
H H17B 0.862726 0.386057 0.668233 0.062 Uiso calc 1 . .
H H17C 0.945213 0.434835 0.768997 0.062 Uiso calc 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 N1 C2 . . 116.3(3) ?
O2 N1 O1 . . 125.6(2) yes
O2 N1 C2 . . 118.1(2) ?
O3 N2 O4 . . 125.4(2) yes
O3 N2 C3 . . 117.5(2) ?
O4 N2 C3 . . 117.1(2) ?
O5 C4 C3 . . 120.13(19) ?
O5 C4 C5 . . 122.0(2) ?
O5 C16 H16A . . 109.5 ?
O5 C16 H16B . . 109.5 ?
O5 C16 H16C . . 109.5 ?
O6 C5 C4 . . 114.47(19) ?
O6 C5 C6 . . 125.36(19) ?
O6 C17 H17A . . 109.5 ?
O6 C17 H17B . . 109.5 ?
O6 C17 H17C . . 109.5 ?
O7 C7 C1 . . 108.12(17) ?
O7 C7 C8 . . 108.20(18) ?
O7 C7 H7 . . 108.7 ?
O8 C11 O7 . . 123.68(19) ?
O8 C11 N3 . . 126.3(2) ?
N3 C12 H12A . . 108.8 ?
N3 C12 H12B . . 108.8 ?
N3 C12 C13 . . 113.99(19) ?
N3 C11 O7 . . 110.05(18) ?
C1 C6 H6 . . 119.0 ?
C1 C2 N1 . . 120.0(2) yes
C1 C2 C3 . . 121.2(2) ?
C1 C7 C8 . . 114.22(18) ?
C1 C7 H7 . . 108.7 ?
C2 C3 N2 . . 119.8(2) ?
C2 C1 C6 . . 117.2(2) ?
C2 C1 C7 . . 122.5(2) ?
C3 C4 C5 . . 117.5(2) ?
C3 C2 N1 . . 118.75(19) ?
C4 O5 C16 . . 115.31(19) yes
C4 C3 N2 . . 118.2(2) yes
C4 C3 C2 . . 121.9(2) ?
C5 O6 C17 . . 117.76(18) yes
C5 C6 C1 . . 121.93(19) ?
C5 C6 H6 . . 119.0 ?
C6 C1 C7 . . 120.26(19) ?
C6 C5 C4 . . 120.2(2) ?
C7 C8 H8 . . 107.3 ?
C8 C7 H7 . . 108.7 ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
C8 C10 H10A . . 109.5 ?
C8 C10 H10B . . 109.5 ?
C8 C10 H10C . . 109.5 ?
C9 C8 H8 . . 107.3 ?
C9 C8 C7 . . 113.8(2) ?
C10 C8 H8 . . 107.3 ?
C10 C8 C7 . . 110.0(2) ?
C10 C8 C9 . . 110.8(2) ?
C11 O7 C7 . . 115.47(17) yes
C11 N3 C12 . . 122.75(19) yes
C11 N3 H3 . . 114.4(19) ?
C12 N3 H3 . . 122.3(19) ?
C12 C13 H13A . . 109.3 ?
C12 C13 H13B . . 109.3 ?
C12 C13 C14 . . 111.8(2) ?
C13 C12 H12A . . 108.8 ?
C13 C12 H12B . . 108.8 ?
C13 C14 H14A . . 109.0 ?
C13 C14 H14B . . 109.0 ?
C14 C13 H13A . . 109.3 ?
C14 C13 H13B . . 109.3 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
C15 C14 C13 . . 112.9(2) ?
C15 C14 H14A . . 109.0 ?
C15 C14 H14B . . 109.0 ?
H9A C9 H9B . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
H10A C10 H10B . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
H12A C12 H12B . . 107.7 ?
H13A C13 H13B . . 107.9 ?
H14A C14 H14B . . 107.8 ?
H15A C15 H15B . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
H16A C16 H16B . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
H17A C17 H17B . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O2 N1 . 1.219(3) yes
O3 N2 . 1.217(3) yes
O5 C4 . 1.363(3) yes
O5 C16 . 1.448(3) yes
O8 C11 . 1.220(3) yes
O6 C5 . 1.351(3) yes
O6 C17 . 1.438(3) yes
O7 C11 . 1.367(3) yes
O7 C7 . 1.447(2) yes
N1 O1 . 1.222(3) yes
N1 C2 . 1.469(3) yes
N2 O4 . 1.220(3) yes
N2 C3 . 1.473(3) yes
N3 C11 . 1.332(3) yes
N3 C12 . 1.455(3) yes
N3 H3 . 0.78(3) ?
C1 C6 . 1.402(3) ?
C1 C2 . 1.383(3) ?
C1 C7 . 1.517(3) yes
C3 C2 . 1.394(3) ?
C4 C3 . 1.374(3) ?
C4 C5 . 1.416(3) ?
C6 H6 . 0.9300 ?
C6 C5 . 1.382(3) ?
C7 H7 . 0.9800 ?
C8 H8 . 0.9800 ?
C8 C7 . 1.529(3) yes
C8 C9 . 1.525(4) yes
C8 C10 . 1.518(4) yes
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C12 C13 . 1.513(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C13 C14 . 1.524(3) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C14 C15 . 1.508(4) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3 O8 2_565 0.78(3) 2.26(3) 3.042(3) 176(3) 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 N1 C2 C1 . . . . -122.5(2) yes
O1 N1 C2 C3 . . . . 53.9(3) ?
O2 N1 C2 C1 . . . . 56.9(3) yes
O2 N1 C2 C3 . . . . -126.7(2) ?
O3 N2 C3 C4 . . . . 56.7(3) ?
O3 N2 C3 C2 . . . . -125.9(3) yes
O4 N2 C3 C4 . . . . -123.5(2) ?
O4 N2 C3 C2 . . . . 53.9(3) yes
O5 C4 C3 N2 . . . . 8.2(3) ?
O5 C4 C3 C2 . . . . -169.1(2) ?
O5 C4 C5 O6 . . . . -8.0(3) yes
O5 C4 C5 C6 . . . . 170.6(2) ?
N2 C3 C2 N1 . . . . 4.4(3) yes
N2 C3 C2 C1 . . . . -179.3(2) ?
N3 C12 C13 C14 . . . . -178.41(19) ?
C1 C6 C5 O6 . . . . 177.1(2) ?
C1 C6 C5 C4 . . . . -1.4(3) ?
C2 C1 C7 O7 . . . . 142.3(2) ?
C2 C1 C7 C8 . . . . -97.2(3) ?
C2 C1 C6 C5 . . . . 3.6(3) ?
C3 C4 C5 O6 . . . . 178.9(2) ?
C3 C4 C5 C6 . . . . -2.5(3) ?
C4 C3 C2 N1 . . . . -178.3(2) ?
C4 C3 C2 C1 . . . . -2.0(3) ?
C5 C4 C3 N2 . . . . -178.5(2) ?
C5 C4 C3 C2 . . . . 4.2(3) ?
C6 C1 C2 N1 . . . . 174.4(2) ?
C6 C1 C2 C3 . . . . -1.9(3) ?
C6 C1 C7 O7 . . . . -36.3(3) ?
C6 C1 C7 C8 . . . . 84.2(2) ?
C7 O7 C11 O8 . . . . -15.0(3) ?
C7 O7 C11 N3 . . . . 165.85(18) ?
C7 C1 C6 C5 . . . . -177.8(2) ?
C7 C1 C2 N1 . . . . -4.3(3) yes
C7 C1 C2 C3 . . . . 179.4(2) ?
C9 C8 C7 O7 . . . . 58.3(3) ?
C9 C8 C7 C1 . . . . -62.1(3) ?
C10 C8 C7 O7 . . . . -66.6(2) ?
C10 C8 C7 C1 . . . . 172.9(2) ?
C11 O7 C7 C1 . . . . -86.6(2) ?
C11 O7 C7 C8 . . . . 149.19(18) ?
C11 N3 C12 C13 . . . . -106.4(2) ?
C12 N3 C11 O7 . . . . 176.03(19) ?
C12 N3 C11 O8 . . . . -3.1(4) ?
C12 C13 C14 C15 . . . . -178.9(2) ?
C16 O5 C4 C3 . . . . -110.7(2) yes
C16 O5 C4 C5 . . . . 76.3(3) ?
C17 O6 C5 C4 . . . . 172.5(2) yes
C17 O6 C5 C6 . . . . -6.0(3) ?
