#------------------------------------------------------------------------------
#$Date: 2020-06-05 05:02:17 +0300 (Fri, 05 Jun 2020) $
#$Revision: 252661 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/06/7240630.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_7240630
loop_
_publ_author_name
'Bryndal, Iwona'
'Drozd, Marek'
'Lis, Tadeusz'
'Zaręba, Jan Kazimierz'
'Ratajczak, Henryk'
_publ_section_title
;
 Structural diversity of hydrogen-bonded complexes comprising phenol-based
 and pyridine-based components: NLO properties, crystallographic and
 spectroscopic studies
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00606H
_journal_year                    2020
_chemical_formula_moiety         'C6 H4 N2 O5'
_chemical_formula_sum            'C6 H4 N2 O5'
_chemical_formula_weight         184.11
_chemical_name_common            2,5-Dinitrophenol
_chemical_name_systematic        2,5-Dinitrophenol
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2020-03-19 deposited with the CCDC.	2020-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.28(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.4780(15)
_cell_length_b                   5.2268(15)
_cell_length_c                   12.296(3)
_cell_measurement_reflns_used    630
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.751
_cell_measurement_theta_min      3.351
_cell_volume                     347.46(17)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3359
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0856
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            1693
_diffrn_reflns_point_group_measured_fraction_full 0.652
_diffrn_reflns_point_group_measured_fraction_max 0.592
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.815
_diffrn_reflns_theta_min         3.358
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_description       plate
_exptl_crystal_F_000             188
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details
;
 Flack x determined using 81 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -9.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1072
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0771
_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)+(0.0955P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1764
_refine_ls_wR_factor_ref         0.2074
_reflns_Friedel_coverage         0.191
_reflns_Friedel_fraction_full    0.242
_reflns_Friedel_fraction_max     0.213
_reflns_number_gt                797
_reflns_number_total             1072
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00606h2.cif
_cod_data_source_block           34LGF1
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7240630
_shelx_shelxl_version_number     2018/1
_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_min   0.977
_shelx_estimated_absorpt_t_max   0.994
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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_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
C1 C 0.1638(10) 0.6864(12) 0.3334(5) 0.0253(14) Uani 1 1 d . . . . .
C2 C 0.3667(10) 0.8277(12) 0.3091(5) 0.0209(12) Uani 1 1 d . . . . .
C3 C 0.4806(10) 0.7710(13) 0.2178(4) 0.0265(14) Uani 1 1 d . . . . .
H3 H 0.619458 0.867452 0.204108 0.032 Uiso 1 1 calc R U . . .
C4 C 0.3904(10) 0.5748(12) 0.1480(5) 0.0253(13) Uani 1 1 d . . . . .
H4 H 0.463369 0.533436 0.085237 0.030 Uiso 1 1 calc R U . . .
C5 C 0.1900(10) 0.4409(12) 0.1730(5) 0.0251(13) Uani 1 1 d . . . . .
C6 C 0.0736(10) 0.4910(11) 0.2617(4) 0.0234(12) Uani 1 1 d . . . . .
H6 H -0.066031 0.393572 0.273681 0.028 Uiso 1 1 calc R U . . .
O1 O 0.0454(7) 0.7263(9) 0.4195(3) 0.0324(11) Uani 1 1 d . . . . .
H1 H 0.129850 0.824658 0.464761 0.049 Uiso 1 1 calc R U . . .
N1 N 0.4642(8) 1.0416(11) 0.3798(4) 0.0246(11) Uani 1 1 d . . . . .
O2 O 0.3599(7) 1.0995(8) 0.4582(3) 0.0304(11) Uani 1 1 d . . . . .
O3 O 0.6448(7) 1.1584(10) 0.3568(3) 0.0343(11) Uani 1 1 d . . . . .
N2 N 0.0891(9) 0.2290(11) 0.0983(4) 0.0279(12) Uani 1 1 d . . . . .
O4 O 0.2083(7) 0.1590(9) 0.0291(3) 0.0330(11) Uani 1 1 d . . . . .
O5 O -0.1096(8) 0.1351(10) 0.1115(3) 0.0363(12) 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
O1 C1 C6 116.6(5) . . ?
O1 C1 C2 125.7(6) . . ?
C6 C1 C2 117.7(5) . . ?
C3 C2 C1 121.9(5) . . ?
C3 C2 N1 118.1(5) . . ?
C1 C2 N1 120.0(5) . . ?
C4 C3 C2 119.7(5) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 117.3(5) . . ?
C3 C4 H4 121.3 . . ?
C5 C4 H4 121.3 . . ?
C6 C5 C4 124.6(6) . . ?
C6 C5 N2 117.2(5) . . ?
C4 C5 N2 118.1(5) . . ?
C5 C6 C1 118.8(5) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
C1 O1 H1 109.5 . . ?
O3 N1 O2 123.1(6) . . ?
O3 N1 C2 118.1(5) . . ?
O2 N1 C2 118.7(5) . . ?
O4 N2 O5 124.2(6) . . ?
O4 N2 C5 118.0(5) . . ?
O5 N2 C5 117.8(5) . . ?
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
C1 O1 1.344(7) . ?
C1 C6 1.387(8) . ?
C1 C2 1.406(8) . ?
C2 C3 1.401(7) . ?
C2 N1 1.463(8) . ?
C3 C4 1.377(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(7) . ?
C5 N2 1.487(8) . ?
C6 H6 0.9500 . ?
O1 H1 0.8400 . ?
N1 O3 1.234(6) . ?
N1 O2 1.234(5) . ?
N2 O4 1.210(6) . ?
N2 O5 1.228(6) . ?
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
O1 H1 O2 0.84 1.92 2.595(6) 136.4 . yes
O1 H1 N1 0.84 2.52 2.928(7) 111.1 . yes
O1 H1 O3 0.84 2.49 3.011(6) 120.8 2_646 yes
C3 H3 O5 0.95 2.45 3.364(8) 161.4 1_665 yes
C4 H4 O4 0.95 2.54 3.364(7) 145.0 2_655 yes
C6 H6 O3 0.95 2.36 3.286(7) 163.4 1_445 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
O1 C1 C2 C3 179.4(6) . . . . ?
C6 C1 C2 C3 -1.8(8) . . . . ?
O1 C1 C2 N1 -0.9(8) . . . . ?
C6 C1 C2 N1 178.0(5) . . . . ?
C1 C2 C3 C4 1.2(8) . . . . ?
N1 C2 C3 C4 -178.5(5) . . . . ?
C2 C3 C4 C5 -0.5(8) . . . . ?
C3 C4 C5 C6 0.6(9) . . . . ?
C3 C4 C5 N2 179.7(5) . . . . ?
C4 C5 C6 C1 -1.2(8) . . . . ?
N2 C5 C6 C1 179.6(5) . . . . ?
O1 C1 C6 C5 -179.3(5) . . . . ?
C2 C1 C6 C5 1.7(8) . . . . ?
C3 C2 N1 O3 -1.3(8) . . . . ?
C1 C2 N1 O3 178.9(5) . . . . ?
C3 C2 N1 O2 177.4(5) . . . . ?
C1 C2 N1 O2 -2.4(7) . . . . ?
C6 C5 N2 O4 -170.0(5) . . . . ?
C4 C5 N2 O4 10.8(8) . . . . ?
C6 C5 N2 O5 9.6(7) . . . . ?
C4 C5 N2 O5 -169.7(5) . . . . ?
