#------------------------------------------------------------------------------
#$Date: 2021-10-06 17:53:52 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269686 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/33/7243374.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_7243374
loop_
_publ_author_name
'Saunders, Lucy K.'
'Pallipurath, Anuradha R.'
'Gutmann, Matthias J.'
'Nowell, Harriott'
'Zhang, Ningjin'
'Allan, David R.'
_publ_section_title
;
 A quantum crystallographic approach to short hydrogen bonds.
;
_journal_issue                   35
_journal_name_full               CrystEngComm
_journal_page_first              6180
_journal_page_last               6190
_journal_paper_doi               10.1039/d1ce00355k
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C7 H3 N2 O6, C3 H9 N2 O1'
_chemical_formula_sum            'C10 H12 N4 O7'
_chemical_formula_weight         300.23
_chemical_name_systematic        'N,N-dimethylurea 2,4-dinitrobenzoate 1:1'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-03-05 deposited with the CCDC.	2021-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.157(6)
_cell_length_b                   5.791(2)
_cell_length_c                   22.956(7)
_cell_measurement_temperature    100(2)
_cell_volume                     2546.7(14)
_computing_cell_refinement       'SXD2001 (Gutmann, 2005)'
_computing_data_collection       'SXD2001 (Gutmann, 2005)'
_computing_data_reduction        'SXD2001 (Gutmann, 2005)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.466
_diffrn_measured_fraction_theta_max 0.136
_diffrn_measurement_device_type  SXD
_diffrn_measurement_method       'time-of-flight LAUE diffraction'
_diffrn_radiation_type           neutron
_diffrn_radiation_wavelength     0.25
_diffrn_reflns_av_unetI/netI     0.1417
_diffrn_reflns_Laue_measured_fraction_full 0.466
_diffrn_reflns_Laue_measured_fraction_max 0.136
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            4992
_diffrn_reflns_point_group_measured_fraction_full 0.466
_diffrn_reflns_point_group_measured_fraction_max 0.136
_diffrn_reflns_theta_full        25.481
_diffrn_reflns_theta_max         86.131
_diffrn_reflns_theta_min         10.367
_diffrn_source                   'ISIS spallation source'
_exptl_absorpt_coefficient_mu    '0.3505 + 0.0020 * lambda'
_exptl_absorpt_correction_T_max  0.2330
_exptl_absorpt_correction_T_min  0.1238
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Gauss integration'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             797
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol, acetonitrile'
_exptl_crystal_size_max          7.000
_exptl_crystal_size_mid          1.500
_exptl_crystal_size_min          1.500
_refine_diff_density_max         1.462
_refine_diff_density_min         -1.300
_refine_diff_density_rms         0.299
_refine_ls_extinction_coef       0.00049(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0886
_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)+(0.1569P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2142
_refine_ls_wR_factor_ref         0.2274
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4558
_reflns_number_total             4992
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00355k2.cif
_cod_data_source_block           system2_NEUT
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Numerical' was
changed to 'numerical' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7243373--7243378.cif.
;
_cod_original_cell_volume        2546.9(14)
_cod_database_code               7243374
_shelx_shelxl_version_number     2016/6
_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+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_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
H3 H 0.3066(10) -0.027(6) 0.1054(8) 0.051(9) Uani 1 1 d . . . . .
H6 H 0.4075(9) 0.209(4) 0.2961(7) 0.032(6) Uani 1 1 d . . . . .
H4 H 0.2842(10) -0.267(5) 0.1943(8) 0.036(6) Uani 1 1 d . . . . .
H1B H 0.4815(8) 0.733(6) -0.0434(8) 0.049(8) Uani 1 1 d . . . . .
H1A H 0.4335(9) 0.555(5) 0.0068(9) 0.029(5) Uani 1 1 d . . . . .
H10C H 0.4438(12) 0.973(6) -0.1304(10) 0.057(9) Uani 1 1 d . . . . .
H10B H 0.4353(13) 1.255(7) -0.1073(12) 0.064(9) Uani 1 1 d . . . . .
H9B H 0.3318(15) 1.332(7) -0.0569(16) 0.073(11) Uani 1 1 d . . . . .
H10A H 0.4886(11) 1.064(6) -0.0681(10) 0.060(9) Uani 1 1 d . . . . .
H9C H 0.2957(12) 1.139(8) -0.1031(12) 0.095(15) Uani 1 1 d . . . . .
H9A H 0.2810(12) 1.119(5) -0.0299(12) 0.070(10) Uani 1 1 d . . . . .
H1 H 0.3334(9) 0.652(4) 0.0449(8) 0.030(6) Uani 1 1 d . . . . .
C2 C 0.3698(4) 0.2192(19) 0.1503(3) 0.011(2) Uani 1 1 d . . . . .
O3 O 0.4204(5) 0.306(3) 0.0581(4) 0.024(4) Uani 1 1 d . . . . .
O2 O 0.3330(5) 0.520(3) 0.0910(5) 0.023(3) Uani 1 1 d . . . . .
N3 N 0.4418(3) 0.4880(15) 0.2100(3) 0.0189(18) Uani 1 1 d . . . . .
C7 C 0.3974(4) 0.281(2) 0.2046(4) 0.016(2) Uani 1 1 d . . . . .
N4 N 0.3306(3) -0.1769(15) 0.3025(3) 0.0196(19) Uani 1 1 d . . . . .
C1 C 0.3773(4) 0.361(2) 0.0952(4) 0.017(3) Uani 1 1 d . . . . .
C5 C 0.3448(4) -0.041(2) 0.2496(4) 0.017(3) Uani 1 1 d . . . . .
O4 O 0.4528(5) 0.562(3) 0.2591(5) 0.026(4) Uani 1 1 d . . . . .
C6 C 0.3846(4) 0.158(2) 0.2555(4) 0.020(3) Uani 1 1 d . . . . .
C3 C 0.3290(4) 0.017(2) 0.1475(4) 0.017(3) Uani 1 1 d . . . . .
C4 C 0.3167(4) -0.111(2) 0.1968(4) 0.021(3) Uani 1 1 d . . . . .
O6 O 0.3545(6) -0.108(3) 0.3485(4) 0.027(3) Uani 1 1 d . . . . .
O7 O 0.2966(5) -0.353(3) 0.2980(5) 0.027(3) Uani 1 1 d . . . . .
O5 O 0.4654(6) 0.569(3) 0.1655(5) 0.030(4) Uani 1 1 d . . . . .
O1 O 0.3267(5) 0.788(3) 0.0084(4) 0.020(3) Uani 1 1 d . . . . .
N2 N 0.3806(3) 1.0168(15) -0.0559(3) 0.021(2) Uani 1 1 d . . . . .
C8 C 0.3812(4) 0.833(2) -0.0222(4) 0.020(3) Uani 1 1 d . . . . .
N1 N 0.4371(3) 0.6949(17) -0.0192(3) 0.0196(19) Uani 1 1 d . . . . .
C10 C 0.4403(5) 1.079(3) -0.0920(5) 0.020(3) Uani 1 1 d . . . . .
C9 C 0.3189(5) 1.163(3) -0.0616(5) 0.023(3) 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 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C2 C3 117.5(9) . . ?
C7 C2 C1 124.7(10) . . ?
C3 C2 C1 117.7(8) . . ?
O5 N3 O4 125.2(11) . . ?
O5 N3 C7 117.3(9) . . ?
O4 N3 C7 117.5(9) . . ?
C6 C7 C2 123.6(10) . . ?
C6 C7 N3 116.5(8) . . ?
C2 C7 N3 119.9(8) . . ?
O7 N4 O6 123.4(11) . . ?
O7 N4 C5 118.5(9) . . ?
O6 N4 C5 118.1(10) . . ?
O3 C1 O2 126.2(11) . . ?
O3 C1 C2 120.1(11) . . ?
O2 C1 C2 113.5(9) . . ?
C4 C5 C6 122.7(10) . . ?
C4 C5 N4 119.5(10) . . ?
C6 C5 N4 117.7(8) . . ?
C7 C6 C5 116.0(8) . . ?
C4 C3 C2 120.4(9) . . ?
C3 C4 C5 119.7(11) . . ?
C8 N2 C10 121.8(8) . . ?
C8 N2 C9 122.0(7) . . ?
C10 N2 C9 116.2(9) . . ?
O1 C8 N2 118.5(10) . . ?
O1 C8 N1 120.0(11) . . ?
N2 C8 N1 121.4(8) . . ?
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
C2 C7 1.401(12) . ?
C2 C3 1.408(14) . ?
C2 C1 1.516(12) . ?
O3 C1 1.229(13) . ?
O2 C1 1.257(16) . ?
N3 O5 1.212(13) . ?
N3 O4 1.225(13) . ?
N3 C7 1.477(13) . ?
C7 C6 1.388(14) . ?
N4 O7 1.216(15) . ?
N4 O6 1.217(13) . ?
N4 C5 1.472(12) . ?
C5 C4 1.387(14) . ?
C5 C6 1.390(15) . ?
C3 C4 1.376(14) . ?
O1 C8 1.287(13) . ?
N2 C8 1.316(13) . ?
N2 C10 1.458(12) . ?
N2 C9 1.460(13) . ?
C8 N1 1.336(12) . ?
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
O1 H1 O3 1.16(3) 2.62(3) 3.506(19) 132.4(12) .
O1 H1 O3 1.16(3) 2.62(3) 3.506(19) 132.4(12) .
