#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/17/1501761.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_1501761
loop_
_publ_author_name
'Lee, Jong Hoon'
'Naumov, Pance'
'Chung, Ihn Hee'
'Lee, Sang Cheol'
_publ_section_title
;
 Solid-state thermochromism and phase transitions of charge transfer
 1,3-diamino-4,6-dinitrobenzene dyes.
;
_journal_issue                   35
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              10087
_journal_page_last               10096
_journal_paper_doi               10.1021/jp205793b
_journal_volume                  115
_journal_year                    2011
_chemical_formula_sum            'C18 H14 N4 O4'
_chemical_formula_weight         350.33
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 102.4450(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2057(2)
_cell_length_b                   9.0165(2)
_cell_length_c                   21.1691(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1715.82(7)
_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 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker SMART APEX2 diffractometer'
_diffrn_measurement_method       'φ and 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  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            25658
_diffrn_reflns_theta_full        29.98
_diffrn_reflns_theta_max         29.98
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9970
_exptl_absorpt_correction_T_min  0.9606
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            'bright yellow'
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0527
_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)+(0.0638P)²+0.3590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1572
_reflns_number_gt                2969
_reflns_number_total             4780
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp205793b_si_004.cif
_cod_data_source_block           lee5_2_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_original_formula_sum        C18H14N4O4
_cod_database_code               1501761
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C3 C 0.58710(16) 0.17446(16) 0.02523(7) 0.0455(3) Uani 1 1 d .
C2 C 0.51625(16) 0.24418(16) -0.03385(7) 0.0455(3) Uani 1 1 d .
C5 C 0.35423(17) 0.15041(16) 0.05750(7) 0.0458(3) Uani 1 1 d .
N4 N 0.74393(15) 0.14584(16) 0.04241(7) 0.0551(3) Uani 1 1 d .
C1 C 0.36347(16) 0.26434(17) -0.04400(7) 0.0482(4) Uani 1 1 d .
H1 H 0.3156 0.3104 -0.0821 0.058 Uiso 1 1 calc R
C6 C 0.27722(16) 0.21987(16) -0.00067(7) 0.0459(3) Uani 1 1 d .
N1 N 0.59116(17) 0.28961(18) -0.07908(6) 0.0582(4) Uani 1 1 d .
C4 C 0.50486(18) 0.12926(16) 0.06880(7) 0.0471(3) Uani 1 1 d .
H4 H 0.5528 0.0832 0.1069 0.057 Uiso 1 1 calc R
N3 N 0.27987(17) 0.10132(15) 0.10722(7) 0.0572(4) Uani 1 1 d .
N2 N 0.12896(15) 0.24246(17) -0.01494(7) 0.0574(4) Uani 1 1 d .
C7 C 0.05269(17) 0.31796(19) -0.07178(8) 0.0531(4) Uani 1 1 d .
O2 O 0.79807(14) 0.09228(18) 0.09498(6) 0.0800(4) Uani 1 1 d .
C13 C 0.52191(19) 0.3651(2) -0.13697(8) 0.0560(4) Uani 1 1 d .
O1 O 0.82088(13) 0.17556(18) 0.00272(6) 0.0756(4) Uani 1 1 d .
O4 O 0.14439(15) 0.11261(16) 0.09841(7) 0.0777(4) Uani 1 1 d .
O3 O 0.35396(16) 0.0494(2) 0.15684(7) 0.0918(5) Uani 1 1 d .
C8 C -0.0281(2) 0.2402(2) -0.12256(9) 0.0694(5) Uani 1 1 d .
H8 H -0.0328 0.1373 -0.1208 0.083 Uiso 1 1 calc R
C12 C 0.0596(2) 0.4703(2) -0.07437(10) 0.0734(5) Uani 1 1 d .
H12 H 0.1143 0.5233 -0.0395 0.088 Uiso 1 1 calc R
C11 C -0.0145(3) 0.5435(3) -0.12862(12) 0.0921(7) Uani 1 1 d .
H11 H -0.0095 0.6464 -0.1306 0.111 Uiso 1 1 calc R
C9 C -0.1031(3) 0.3154(3) -0.17673(10) 0.0911(7) Uani 1 1 d .
H9 H -0.1590 0.2629 -0.2114 0.109 Uiso 1 1 calc R
C18 C 0.4914(4) 0.5098(3) -0.13574(11) 0.1096(9) Uani 1 1 d .
H18 H 0.5143 0.5613 -0.0968 0.132 Uiso 1 1 calc R
C14 C 0.4876(3) 0.2912(3) -0.19391(10) 0.1032(9) Uani 1 1 d .
H14 H 0.5073 0.1902 -0.1954 0.124 Uiso 1 1 calc R
C10 C -0.0955(3) 0.4664(3) -0.17954(12) 0.0946(8) Uani 1 1 d .
H10 H -0.1455 0.5165 -0.2162 0.113 Uiso 1 1 calc R
C15 C 0.4234(4) 0.3660(4) -0.24955(11) 0.1255(12) Uani 1 1 d .
H15 H 0.3996 0.3146 -0.2885 0.151 Uiso 1 1 calc R
C17 C 0.4260(4) 0.5832(3) -0.19185(13) 0.1326(13) Uani 1 1 d .
H17 H 0.4035 0.6835 -0.1902 0.159 Uiso 1 1 calc R
C16 C 0.3945(3) 0.5121(3) -0.24873(11) 0.0963(7) Uani 1 1 d .
H16 H 0.3535 0.5625 -0.2867 0.116 Uiso 1 1 calc R
H2N H 0.079(2) 0.203(2) 0.0105(9) 0.070(6) Uiso 1 1 d .
H1N H 0.684(2) 0.271(2) -0.0703(9) 0.070(6) Uiso 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'
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
C4 C3 C2 120.34(14)
C4 C3 N4 116.50(14)
C2 C3 N4 123.16(13)
N1 C2 C1 120.18(14)
N1 C2 C3 123.06(14)
C1 C2 C3 116.76(13)
C4 C5 C6 120.55(13)
C4 C5 N3 116.85(13)
C6 C5 N3 122.59(13)
O2 N4 O1 121.63(14)
O2 N4 C3 119.66(13)
O1 N4 C3 118.71(14)
C2 C1 C6 124.17(14)
N2 C6 C1 120.09(14)
N2 C6 C5 123.40(13)
C1 C6 C5 116.51(13)
C2 N1 C13 123.28(14)
C5 C4 C3 121.67(14)
O3 N3 O4 121.78(14)
O3 N3 C5 118.83(14)
O4 N3 C5 119.40(13)
C6 N2 C7 123.43(13)
C8 C7 C12 120.28(17)
C8 C7 N2 120.34(16)
C12 C7 N2 119.37(16)
C18 C13 C14 119.23(19)
C18 C13 N1 120.40(17)
C14 C13 N1 120.36(18)
C7 C8 C9 119.5(2)
C11 C12 C7 119.6(2)
C10 C11 C12 120.4(2)
C10 C9 C8 120.3(2)
C13 C18 C17 120.4(2)
C13 C14 C15 119.7(2)
C11 C10 C9 119.9(2)
C16 C15 C14 121.3(2)
C16 C17 C18 120.9(2)
C17 C16 C15 118.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C3 C4 1.375(2)
C3 C2 1.426(2)
C3 N4 1.434(2)
C2 N1 1.3582(19)
C2 C1 1.388(2)
C5 C4 1.369(2)
C5 C6 1.426(2)
C5 N3 1.4433(19)
N4 O2 1.2170(18)
N4 O1 1.2393(17)
C1 C6 1.395(2)
C6 N2 1.348(2)
N1 C13 1.426(2)
N3 O3 1.2160(18)
N3 O4 1.2249(19)
N2 C7 1.428(2)
C7 C8 1.362(3)
C7 C12 1.376(3)
C13 C18 1.336(3)
C13 C14 1.354(3)
C8 C9 1.382(3)
C12 C11 1.372(3)
C11 C10 1.362(3)
C9 C10 1.365(4)
C18 C17 1.380(3)
C14 C15 1.375(3)
C15 C16 1.345(4)
C17 C16 1.340(3)
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
N2 H2N O4 0.86(2) 2.00(2) 2.6462(18) 131.2(17) .
N2 H2N O1 0.86(2) 2.359(19) 3.0007(18) 132.0(16) 1_455
N1 H1N O1 0.85(2) 1.97(2) 2.636(2) 134.3(17) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2642589
2 PubChem 3398091
