#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/63/1516376.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_1516376
loop_
_publ_author_name
'Naumov, Pance'
'Lee, Sang Cheol'
'Ishizawa, Nobuo'
'Jeong, Young Gyu'
'Chung, Ihn Hee'
'Fukuzumi, Shunichi'
_publ_section_title
;
 New type of dual solid-state thermochromism: modulation of intramolecular
 charge transfer by intermolecular pi-pi interactions, kinetic trapping of
 the aci-nitro group, and reversible molecular locking.
;
_journal_issue                   42
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              11354
_journal_page_last               11366
_journal_paper_doi               10.1021/jp902517x
_journal_volume                  113
_journal_year                    2009
_chemical_formula_moiety         'C10 H14 N4 O6'
_chemical_formula_sum            'C10 H14 N4 O6'
_chemical_formula_weight         286.25
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.4174(2)
_cell_length_b                   7.01760(10)
_cell_length_c                   19.3440(2)
_cell_measurement_temperature    293(2)
_cell_volume                     2364.39(5)
_computing_cell_refinement       'APEX2 software (Bruker, 2007)'
_computing_data_collection       'APEX2 software (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2005)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX2 diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'multilayer confocal TXS mirror'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            41409
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.9973
_exptl_absorpt_correction_T_min  0.9814
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0417P)²+1.1398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                2156
_reflns_number_total             2710
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp902517x_si_002.cif
_cod_data_source_block           bdb_21
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1516376
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
H1N H -0.2265(10) 0.222(3) 0.5707(9) 0.035(5) Uiso 1 1 d .
H4N H 0.1256(10) 0.328(3) 0.5436(10) 0.036(5) Uiso 1 1 d .
H5O H -0.0790(13) 0.370(4) 0.7585(12) 0.065(7) Uiso 1 1 d .
H6O H 0.0189(12) 0.152(3) 0.7094(10) 0.052(6) Uiso 1 1 d .
N3 N 0.07642(7) 0.22445(18) 0.41968(6) 0.0279(3) Uani 1 1 d .
C6 C 0.01897(7) 0.28477(19) 0.53751(7) 0.0223(3) Uani 1 1 d .
O6 O 0.05980(7) 0.10430(16) 0.69644(6) 0.0351(3) Uani 1 1 d .
O4 O 0.14185(6) 0.24461(19) 0.44285(6) 0.0427(3) Uani 1 1 d .
N2 N -0.19304(7) 0.12871(19) 0.44313(6) 0.0300(3) Uani 1 1 d .
N4 N 0.08617(7) 0.33070(19) 0.56714(6) 0.0277(3) Uani 1 1 d .
O3 O 0.06535(7) 0.2022(2) 0.35771(6) 0.0497(4) Uani 1 1 d .
N1 N -0.18447(7) 0.2493(2) 0.58843(6) 0.0314(3) Uani 1 1 d .
O2 O -0.19544(7) 0.1305(2) 0.37959(6) 0.0486(3) Uani 1 1 d .
C3 C -0.12347(8) 0.1830(2) 0.47731(7) 0.0247(3) Uani 1 1 d .
C4 C -0.05772(8) 0.1816(2) 0.43825(7) 0.0243(3) Uani 1 1 d .
H4 H -0.0606 0.1471 0.3919 0.029 Uiso 1 1 calc R
O1 O -0.24903(6) 0.0807(2) 0.47805(6) 0.0450(3) Uani 1 1 d .
C2 C -0.12128(8) 0.24051(19) 0.54865(7) 0.0236(3) Uani 1 1 d .
C1 C -0.04958(8) 0.2894(2) 0.57489(7) 0.0249(3) Uani 1 1 d .
H1 H -0.0471 0.3282 0.6208 0.030 Uiso 1 1 calc R
C5 C 0.01248(8) 0.22985(19) 0.46588(7) 0.0232(3) Uani 1 1 d .
O5 O -0.08132(7) 0.26543(19) 0.73535(6) 0.0393(3) Uani 1 1 d .
C9 C 0.09588(9) 0.4021(2) 0.63717(7) 0.0292(3) Uani 1 1 d .
H9A H 0.0487 0.4639 0.6515 0.035 Uiso 1 1 calc R
H9B H 0.1361 0.4977 0.6371 0.035 Uiso 1 1 calc R
C10 C 0.11605(9) 0.2498(2) 0.68963(8) 0.0338(3) Uani 1 1 d .
H10A H 0.1644 0.1917 0.6764 0.041 Uiso 1 1 calc R
H10B H 0.1234 0.3098 0.7343 0.041 Uiso 1 1 calc R
C7 C -0.18900(9) 0.3406(2) 0.65560(8) 0.0330(4) Uani 1 1 d .
H7A H -0.2423 0.3711 0.6648 0.040 Uiso 1 1 calc R
H7B H -0.1610 0.4600 0.6534 0.040 Uiso 1 1 calc R
C8 C -0.15798(10) 0.2255(3) 0.71638(8) 0.0434(4) Uani 1 1 d .
H8A H -0.1907 0.2483 0.7561 0.052 Uiso 1 1 calc R
H8B H -0.1618 0.0912 0.7050 0.052 Uiso 1 1 calc R
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'
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'
H H 0.0000 0.0000 '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
O3 N3 O4 121.09(12)
O3 N3 C5 119.55(12)
O4 N3 C5 119.35(12)
N4 C6 C1 121.25(12)
N4 C6 C5 122.86(12)
C1 C6 C5 115.89(12)
O2 N2 O1 121.56(12)
O2 N2 C3 119.18(12)
O1 N2 C3 119.27(12)
C6 N4 C9 125.58(12)
C2 N1 C7 125.26(13)
C4 C3 N2 116.75(12)
C4 C3 C2 120.54(12)
N2 C3 C2 122.70(12)
C3 C4 C5 121.71(13)
N1 C2 C1 120.99(13)
N1 C2 C3 122.70(12)
C1 C2 C3 116.31(12)
C2 C1 C6 124.96(12)
C4 C5 N3 116.29(12)
C4 C5 C6 120.55(12)
N3 C5 C6 123.16(12)
N4 C9 C10 114.08(13)
O6 C10 C9 114.14(12)
N1 C7 C8 115.90(14)
O5 C8 C7 115.45(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N3 O3 1.2242(16)
N3 O4 1.2328(16)
N3 C5 1.4284(17)
C6 N4 1.3425(18)
C6 C1 1.3963(18)
C6 C5 1.4425(18)
O6 C10 1.4209(19)
N2 O2 1.2299(16)
N2 O1 1.2333(16)
N2 C3 1.4319(17)
N4 C9 1.4542(18)
N1 C2 1.3445(17)
N1 C7 1.4510(19)
C3 C4 1.3721(19)
C3 C2 1.4384(19)
C4 C5 1.3768(19)
C2 C1 1.3909(19)
O5 C8 1.413(2)
C9 C10 1.515(2)
C7 C8 1.526(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 71352743
