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#$Date: 2025-08-19 22:30:04 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301811 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/00/36/4003678.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_4003678
loop_
_publ_author_name
'Gui, Yue'
'Yao, Xin'
'Guzei, Ilia A.'
'Aristov, Michael M.'
'Yu, Junguang'
'Yu, Lian'
_publ_section_title
;
 A Mechanism for Reversible Solid-State Transitions Involving Nitro
 Torsion
;
_journal_issue                   18
_journal_name_full               'Chemistry of Materials'
_journal_page_first              7754
_journal_page_last               7765
_journal_paper_doi               10.1021/acs.chemmater.0c02209
_journal_volume                  32
_journal_year                    2020
_chemical_formula_moiety         'C17 H18 N2 O6'
_chemical_formula_sum            'C17 H18 N2 O6'
_chemical_formula_weight         346.33
_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             2019-11-01
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.10.24 svn.r3677 for OlexSys, GUI svn.r5967)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.980(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.905(4)
_cell_length_b                   10.908(3)
_cell_length_c                   12.779(4)
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.554
_cell_measurement_theta_min      2.502
_cell_volume                     1587.1(9)
_computing_cell_refinement       'SAINT+ Ver. 2018.1-0. (Bruker-AXS, 2018)'
_computing_data_collection       'APEX3 Ver. 2018.1-0. (Bruker-AXS, 2018)'
_computing_data_reduction        'SAINT+ Ver. 2018.1-0. (Bruker-AXS, 2018)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015b)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Quazar'
_diffrn_measurement_method       '0.5° ω and 0.5° φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       'Bruker APEX II'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            37720
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.596
_diffrn_reflns_theta_min         2.058
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0382
_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)+(0.0513P)²+0.6935P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1076
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4195
_reflns_number_total             4865
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            delta100K.cif
_cod_data_source_block           yu182
_cod_depositor_comments
'Adding full bibliography for 4003674--4003684.cif.'
_cod_original_cell_volume        1587.2(8)
_cod_database_code               4003678
_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.
;
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.962
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C5(H5A,H5B,H5C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C)
;
_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
O1 O 0.47433(8) 0.80080(8) 0.31243(7) 0.02544(18) Uani 1 1 d . . . . .
O2 O 0.51102(7) 0.61843(7) 0.24941(6) 0.01921(16) Uani 1 1 d . . . . .
O3 O 0.80503(7) 0.31050(7) 0.66145(6) 0.02060(16) Uani 1 1 d . . . . .
O4 O 0.72431(7) 0.29583(7) 0.48019(6) 0.01806(16) Uani 1 1 d . . . . .
O5 O 0.56591(7) 0.33984(8) 0.26092(7) 0.02274(17) Uani 1 1 d . . . . .
O6 O 0.60504(9) 0.41121(9) 0.11772(7) 0.0310(2) Uani 1 1 d . . . . .
N1 N 0.64604(8) 0.66594(8) 0.63111(7) 0.01589(17) Uani 1 1 d . . . . .
H1 H 0.6466(12) 0.7085(14) 0.6890(12) 0.019 Uiso 1 1 d . U . . .
N2 N 0.62637(8) 0.40057(9) 0.21780(7) 0.01928(18) Uani 1 1 d . . . . .
C1 C 0.58882(8) 0.71392(9) 0.53011(8) 0.01456(18) Uani 1 1 d . . . . .
C2 C 0.53836(10) 0.83900(10) 0.53612(10) 0.0207(2) Uani 1 1 d . . . . .
H2A H 0.538366 0.855638 0.611485 0.031 Uiso 1 1 calc R U . . .
H2B H 0.457667 0.842237 0.487638 0.031 Uiso 1 1 calc R U . . .
H2C H 0.586128 0.900738 0.513171 0.031 Uiso 1 1 calc R U . . .
C3 C 0.58162(8) 0.64829(9) 0.43812(8) 0.01311(17) Uani 1 1 d . . . . .
C4 C 0.51734(8) 0.69934(9) 0.33106(8) 0.01521(18) Uani 1 1 d . . . . .
C5 C 0.45579(10) 0.66488(12) 0.14083(9) 0.0246(2) Uani 1 1 d . . . . .
H5A H 0.454810 0.600667 0.086944 0.037 Uiso 1 1 calc R U . . .
H5B H 0.499972 0.735752 0.126935 0.037 Uiso 1 1 calc R U . . .
H5C H 0.375063 0.689786 0.134869 0.037 Uiso 1 1 calc R U . . .
C6 C 0.63721(8) 0.52165(8) 0.44154(7) 0.01167(16) Uani 1 1 d . . . . .
H6 H 0.574974 0.462295 0.402655 0.014 Uiso 1 1 calc R U . . .
C7 C 0.69043(8) 0.47763(8) 0.55952(8) 0.01220(17) Uani 1 1 d . . . . .
C8 C 0.74514(8) 0.35548(9) 0.57607(8) 0.01328(17) Uani 1 1 d . . . . .
C9 C 0.78229(10) 0.17986(9) 0.48085(9) 0.0202(2) Uani 1 1 d . . . . .
H9A H 0.784463 0.160339 0.406610 0.030 Uiso 1 1 calc R U . . .
H9B H 0.739210 0.115611 0.506545 0.030 Uiso 1 1 calc R U . . .
H9C H 0.862664 0.184699 0.529844 0.030 Uiso 1 1 calc R U . . .
C10 C 0.69215(8) 0.54928(9) 0.64685(8) 0.01347(17) Uani 1 1 d . . . . .
C11 C 0.73918(9) 0.51705(10) 0.76557(8) 0.01816(19) Uani 1 1 d . . . . .
H11A H 0.818889 0.549809 0.794696 0.027 Uiso 1 1 calc R U . . .
H11B H 0.740977 0.427704 0.773895 0.027 Uiso 1 1 calc R U . . .
H11C H 0.688452 0.552561 0.805796 0.027 Uiso 1 1 calc R U . . .
C12 C 0.73353(8) 0.52379(9) 0.38362(8) 0.01282(17) Uani 1 1 d . . . . .
C13 C 0.83508(9) 0.59059(9) 0.43365(9) 0.01634(19) Uani 1 1 d . . . . .
H13 H 0.839260 0.634856 0.498704 0.020 Uiso 1 1 calc R U . . .
C14 C 0.93029(9) 0.59452(10) 0.39150(10) 0.0208(2) Uani 1 1 d . . . . .
H14 H 0.997731 0.641475 0.427441 0.025 Uiso 1 1 calc R U . . .
C15 C 0.92704(10) 0.53014(11) 0.29721(10) 0.0229(2) Uani 1 1 d . . . . .
H15 H 0.993378 0.529437 0.270168 0.028 Uiso 1 1 calc R U . . .
C16 C 0.82622(10) 0.46692(10) 0.24290(9) 0.0211(2) Uani 1 1 d . . . . .
H16 H 0.821792 0.424673 0.176801 0.025 Uiso 1 1 calc R U . . .
C17 C 0.73124(9) 0.46552(9) 0.28563(8) 0.01571(18) Uani 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O2 C5 114.84(9) . . ?
C8 O4 C9 117.33(8) . . ?
C1 N1 H1 118.2(10) . . ?
C1 N1 C10 123.78(9) . . ?
C10 N1 H1 117.6(10) . . ?
O5 N2 O6 123.25(10) . . ?
O5 N2 C17 120.27(9) . . ?
O6 N2 C17 116.48(9) . . ?
N1 C1 C2 113.19(9) . . ?
C3 C1 N1 120.05(9) . . ?
C3 C1 C2 126.76(9) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 C4 119.39(9) . . ?
C1 C3 C6 122.36(9) . . ?
C4 C3 C6 118.25(8) . . ?
O1 C4 O2 121.25(10) . . ?
O1 C4 C3 127.15(10) . . ?
O2 C4 C3 111.59(8) . . ?
O2 C5 H5A 109.5 . . ?
O2 C5 H5B 109.5 . . ?
O2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6 108.6 . . ?
C3 C6 C7 111.28(8) . . ?
C3 C6 C12 110.54(7) . . ?
C7 C6 H6 108.6 . . ?
C7 C6 C12 109.06(7) . . ?
C12 C6 H6 108.6 . . ?
C8 C7 C6 117.64(8) . . ?
C10 C7 C6 122.08(9) . . ?
C10 C7 C8 120.23(9) . . ?
O3 C8 O4 121.66(9) . . ?
O3 C8 C7 127.75(9) . . ?
O4 C8 C7 110.56(8) . . ?
O4 C9 H9A 109.5 . . ?
O4 C9 H9B 109.5 . . ?
O4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C11 112.34(8) . . ?
C7 C10 N1 120.14(9) . . ?
C7 C10 C11 127.52(9) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C6 117.11(9) . . ?
C13 C12 C17 115.81(9) . . ?
C17 C12 C6 127.08(9) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 C12 122.23(10) . . ?
C14 C13 H13 118.9 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.16(10) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.28(10) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.61(10) . . ?
C17 C16 H16 120.2 . . ?
C12 C17 N2 122.42(9) . . ?
C16 C17 N2 114.80(9) . . ?
C16 C17 C12 122.75(10) . . ?
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
O1 C4 1.2135(13) . ?
O2 C4 1.3519(13) . ?
O2 C5 1.4427(13) . ?
O3 C8 1.2187(12) . ?
O4 C8 1.3449(12) . ?
O4 C9 1.4400(13) . ?
O5 N2 1.2216(13) . ?
O6 N2 1.2345(13) . ?
N1 H1 0.872(15) . ?
N1 C1 1.3749(13) . ?
N1 C10 1.3772(13) . ?
N2 C17 1.4765(14) . ?
C1 C2 1.5017(14) . ?
C1 C3 1.3576(14) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.4684(14) . ?
C3 C6 1.5269(13) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6 1.0000 . ?
C6 C7 1.5321(13) . ?
C6 C12 1.5359(13) . ?
C7 C8 1.4709(14) . ?
C7 C10 1.3578(13) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.4975(14) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.3964(14) . ?
C12 C17 1.3974(14) . ?
C13 H13 0.9500 . ?
C13 C14 1.3905(14) . ?
C14 H14 0.9500 . ?
C14 C15 1.3855(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.3825(17) . ?
C16 H16 0.9500 . ?
C16 C17 1.3920(14) . ?
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
N1 H1 O3 0.872(15) 2.140(15) 2.9919(13) 165.5(13) 2_656 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
O5 N2 C17 C12 -38.83(14) . . . . ?
O5 N2 C17 C16 142.81(10) . . . . ?
O6 N2 C17 C12 141.44(10) . . . . ?
O6 N2 C17 C16 -36.92(13) . . . . ?
N1 C1 C3 C4 178.28(8) . . . . ?
N1 C1 C3 C6 -1.10(14) . . . . ?
C1 N1 C10 C7 5.01(14) . . . . ?
C1 N1 C10 C11 -174.47(9) . . . . ?
C1 C3 C4 O1 5.59(15) . . . . ?
C1 C3 C4 O2 -175.17(8) . . . . ?
C1 C3 C6 C7 4.73(12) . . . . ?
C1 C3 C6 C12 -116.61(10) . . . . ?
C2 C1 C3 C4 -1.05(15) . . . . ?
C2 C1 C3 C6 179.57(9) . . . . ?
C3 C6 C7 C8 178.70(7) . . . . ?
C3 C6 C7 C10 -3.89(12) . . . . ?
C3 C6 C12 C13 68.25(11) . . . . ?
C3 C6 C12 C17 -111.97(11) . . . . ?
C4 C3 C6 C7 -174.65(8) . . . . ?
C4 C3 C6 C12 64.00(10) . . . . ?
C5 O2 C4 O1 3.19(14) . . . . ?
C5 O2 C4 C3 -176.11(8) . . . . ?
C6 C3 C4 O1 -175.01(10) . . . . ?
C6 C3 C4 O2 4.23(12) . . . . ?
C6 C7 C8 O3 169.58(9) . . . . ?
C6 C7 C8 O4 -8.17(11) . . . . ?
C6 C7 C10 N1 -0.56(14) . . . . ?
C6 C7 C10 C11 178.85(9) . . . . ?
C6 C12 C13 C14 176.99(9) . . . . ?
C6 C12 C17 N2 5.75(15) . . . . ?
C6 C12 C17 C16 -176.03(9) . . . . ?
C7 C6 C12 C13 -54.40(11) . . . . ?
C7 C6 C12 C17 125.38(10) . . . . ?
C8 C7 C10 N1 176.79(8) . . . . ?
C8 C7 C10 C11 -3.81(15) . . . . ?
C9 O4 C8 O3 -4.22(14) . . . . ?
C9 O4 C8 C7 173.69(8) . . . . ?
C10 N1 C1 C2 175.25(9) . . . . ?
C10 N1 C1 C3 -4.17(15) . . . . ?
C10 C7 C8 O3 -7.88(15) . . . . ?
C10 C7 C8 O4 174.37(8) . . . . ?
C12 C6 C7 C8 -59.10(10) . . . . ?
C12 C6 C7 C10 118.31(9) . . . . ?
C12 C13 C14 C15 -0.49(16) . . . . ?
C13 C12 C17 N2 -174.47(9) . . . . ?
C13 C12 C17 C16 3.75(14) . . . . ?
C13 C14 C15 C16 3.04(17) . . . . ?
C14 C15 C16 C17 -2.14(16) . . . . ?
C15 C16 C17 N2 176.99(10) . . . . ?
C15 C16 C17 C12 -1.36(16) . . . . ?
C17 C12 C13 C14 -2.82(15) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 4485
