#------------------------------------------------------------------------------
#$Date: 2021-10-06 17:53:52 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269686 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/33/7243376.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_7243376
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         'C1 H1 O2, C3 H8 N2 O1'
_chemical_formula_sum            'C4 H9 N2 O3'
_chemical_formula_weight         133.13
_chemical_name_systematic        'N,N'-dimethylurea oxalic acid 2:1'
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-03-05 deposited with the CCDC.	2021-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.6140(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.81790(10)
_cell_length_b                   13.2171(2)
_cell_length_c                   12.40800(10)
_cell_measurement_reflns_used    23721
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      56.35681599534807
_cell_measurement_theta_min      2.1789248764459797
_cell_volume                     624.10(2)
_computing_cell_refinement
'DIALS 2theta refinement, DIALS 1.14.9-g0c59d74b8-release'
_computing_data_collection       'GDA - generic data acquisition software'
_computing_data_reduction
;
DIALS 1.14.9-g0c59d74b8-release (Winter, G. et al., 2018)
;
_computing_molecular_graphics    MercuryTM
_computing_structure_refinement  'Volkov et al, (2006)'
_computing_structure_solution    SHELXS-2014
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Photon counting pixel array'
_diffrn_detector_type            'Dectris PILATUS 2M'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9065
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         56.505
_diffrn_reflns_theta_min         2.186
_diffrn_source                   Synchrotron
_diffrn_source_details           'Allan et al. (2017)'
_diffrn_source_type              'Diamond Light Source Beamline I19-1'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.132
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max          0.057
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         4702
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.055
_refine_ls_R_factor_gt           0.019
_refine_ls_R_Fsqd_factor         0.026
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w2 = 1/[s²(Fo²)]
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.046
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4702
_reflns_number_total             9065
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00355k2.cif
_cod_data_source_block           system_1_XD
_cod_depositor_comments
;
The following automatic conversions were performed:

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_sg_symbol_H-M      'P 21/n'
_cod_database_code               7243376
_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_min   0.996
_shelx_estimated_absorpt_t_max   0.998
_exptl_sortav_scale_factor_max   2.381
_exptl_sortav_scale_factor_min   0.119
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z
loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
O(1) C(1) X O(1) H(1) Y
O(2) C(1) Z O(2) O(1) Y
O(3) C(2) Z O(3) N(2) Y
N(1) C(2) X N(1) C(3) Y
N(2) H(2A) Z N(2) C(2) Y
C(1) O(2) X C(1) O(1) Y
C(2) O(3) X C(2) N(2) Y
C(3) N(1) Z C(3) H(3C) Y
C(4) N(2) Z C(4) H(4B) Y
H(1) O(1) Z H(1) C(1) Y
H(3C) C(3) Z H(3C) N(1) Y
H(3A) C(3) Z H(3A) N(1) Y
H(3B) C(3) Z H(3B) N(1) Y
H(4A) C(4) Z H(4A) N(2) Y
H(4C) C(4) Z H(4C) N(2) Y
H(4B) C(4) Z H(4B) N(2) Y
H(2A) N(2) Z H(2A) C(2) Y
H(1A) N(1) Z H(1A) C(2) Y
loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
_atom_rho_multipole_radial_slater_n0
_atom_rho_multipole_radial_slater_zeta0
_atom_rho_multipole_radial_slater_n1
_atom_rho_multipole_radial_slater_zeta1
_atom_rho_multipole_radial_slater_n2
_atom_rho_multipole_radial_slater_zeta2
_atom_rho_multipole_radial_slater_n3
_atom_rho_multipole_radial_slater_zeta3
_atom_rho_multipole_radial_slater_n4
_atom_rho_multipole_radial_slater_zeta4
O(1) 6.173(14) 0 -0.050(6) -0.014(6) 0 -0.022(8) 0 0 -0.040(7) 0.014(7) 0
0.016(5) -0.013(5) 0 0 0.047(5) -0.009(5) 0.024(7) 0 0 0.023(7) 0.014(7) 0 0
-0.014(6) -0.001(6) 1.001632 1.113461 1.113461 1.113461 1.113461 1.113461 2
4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(2) 6.153(14) 0 0 0 -0.064(6) -0.011(8) 0 0 -0.084(8) 0 0.004(6) 0 0 0.037(6) 0
0 0 0.013(8) 0 0 0.011(7) 0 0 0 0.023(7) 0 1.003017 1.109004 1.109004 1.109004
1.109004 1.109004 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(3) 6.166(14) 0 0 0 -0.035(6) -0.014(7) 0 0 -0.058(7) 0 0.045(6) 0 0 0.035(5) 0
0 0 0.039(7) 0 0 -0.005(7) 0 0 0 0.000(6) 0 1.003017 1.109004 1.109004 1.109004
1.109004 1.109004 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
N(1) 4.944(16) 0 -0.023(7) 0.015(7) 0 -0.009(7) 0 0 -0.003(7) 0.018(7) 0
0.007(6) 0.004(6) 0 0 0.149(6) 0.003(6) 0.046(9) 0 0 0.006(8) -0.023(8) 0 0
-0.021(7) -0.020(8) 1.006323 1.062557 1.062557 1.062557 1.062557 1.062557 2
3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
N(2) 4.955(17) 0 -0.015(7) 0.019(7) -0.018(8) -0.009(8) -0.004(6) 0.005(7)
0.004(7) 0.015(6) 0.160(7) -0.007(6) -0.023(7) 0.082(7) 0.004(6) -0.027(6)
0.024(7) 0.043(9) 0.025(8) -0.002(8) 0.002(8) -0.009(8) 0.003(8) -0.016(9)
0.020(8) -0.004(7) 1.010014 1.028362 1.028362 1.028362 1.028362 1.028362 2
3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
C(1) 4.004(19) 0 0.083(9) 0.006(8) 0 -0.298(8) 0 0 0.077(8) -0.033(7) 0 0.003(8)
-0.015(8) 0 0 0.322(9) 0.035(9) 0.044(11) 0 0 0.013(11) -0.011(10) 0 0
-0.010(13) -0.007(10) 1.015931 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4
3.1762
C(2) 3.93(2) 0 -0.007(9) -0.042(9) 0 -0.275(8) 0 0 0.017(9) -0.001(8) 0
-0.021(9) 0.013(9) 0 0 0.339(10) 0.028(9) 0.020(12) 0 0 -0.027(11) -0.026(11) 0
0 0.006(13) -0.074(12) 1.016311 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4
3.1762
C(3) 3.92(2) 0 0 0 -0.043(7) -0.035(6) 0 0 0 0 0.263(7) 0 0 0 0 0 -0.165(7)
0.054(9) 0 0 0 0 0 0.059(8) 0 0 1.009611 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(4) 3.9202 0 0 0 -0.0428 -0.0345 0 0 0 0 0.2634 0 0 0 0 0 -0.1648 0.0539 0 0 0
0 0 0.0587 0 0 1.009611 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
H(1) 0.808(14) 0 0 0 0.037(11) 0.085(18) 0 0 0 0 0.0171 0 0 0 0 0 0 -0.0278 0 0
0 0 0 0 0 0 1.119673 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(3C) 1.032(8) 0 0 0 0.157(5) 0.073(7) 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0
0 0 0 0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(3A) 1.0319 0 0 0 0.1572 0.073 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0 0 0
1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(3B) 1.0319 0 0 0 0.1572 0.073 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0 0 0
1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(4A) 1.0319 0 0 0 0.1572 0.073 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0 0 0
1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(4C) 1.0319 0 0 0 0.1572 0.073 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0 0 0
1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(4B) 1.0319 0 0 0 0.1572 0.073 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0 0 0
1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(2A) 0.918(10) 0 0 0 0.192(8) 0.129(10) 0 0 0 0 0.0172 0 0 0 0 0 0 -0.0115 0 0
0 0 0 0 0 0 1.140452 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(1A) 0.918 0 0 0 0.1915 0.1291 0 0 0 0 0.0172 0 0 0 0 0 0 -0.0115 0 0 0 0 0 0 0
0 1.140452 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_U_iso_or_equiv
O(1) 0.73443(6) 0.107208(18) 1.00833(2) 1 4 0.017
O(2) 0.93048(5) 0.030209(13) 0.86318(2) 1 4 0.019
O(3) 0.46109(5) 0.249167(13) 0.90678(2) 1 4 0.018
N(1) 0.34702(5) 0.350486(18) 0.76245(2) 1 4 0.017
N(2) 0.61574(7) 0.194357(19) 0.743211(19) 1 4 0.017
C(1) 0.90613(5) 0.038548(15) 0.960819(16) 1 4 0.014
C(2) 0.47645(5) 0.263999(16) 0.805580(17) 1 4 0.014
C(3) 0.21186(6) 0.428530(17) 0.83043(2) 1 4 0.021
C(4) 0.66348(6) 0.207560(18) 0.629352(18) 1 4 0.020
H(1) 0.606002 0.1705 0.951 1 4 0.045
H(3C) 0.078433 0.484206 0.778156 1 4 0.070
H(3A) 0.413759 0.463971 0.881786 1 4 0.058
H(3B) 0.031745 0.397389 0.886389 1 4 0.046
H(4A) 0.826316 0.145313 0.604635 1 4 0.047
H(4C) 0.800294 0.278098 0.615113 1 4 0.045
H(4B) 0.412767 0.203695 0.581037 1 4 0.045
H(2A) 0.718506 0.132694 0.782774 1 4 0.033
H(1A) 0.383062 0.368576 0.685366 1 4 0.039
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(2) N(1) C(3) 120.70(2) 1_555 1_555 1_555 yes
C(2) N(1) H(1A) 120.55(2) 1_555 1_555 1_555 yes
C(3) N(1) H(1A) 117.73(2) 1_555 1_555 1_555 yes
C(2) N(2) C(4) 124.55(2) 1_555 1_555 1_555 yes
C(2) N(2) H(2A) 115.38(2) 1_555 1_555 1_555 yes
C(4) N(2) H(2A) 119.64(2) 1_555 1_555 1_555 yes
O(1) C(1) O(2) 126.58(2) 1_555 1_555 1_555 yes
O(3) C(2) N(1) 118.63(2) 1_555 1_555 1_555 yes
O(3) C(2) N(2) 120.95(2) 1_555 1_555 1_555 yes
N(1) C(2) N(2) 120.41(2) 1_555 1_555 1_555 yes
N(1) C(3) H(3C) 107.89(2) 1_555 1_555 1_555 yes
N(1) C(3) H(3A) 112.63(2) 1_555 1_555 1_555 yes
N(1) C(3) H(3B) 111.80(2) 1_555 1_555 1_555 yes
H(3C) C(3) H(3A) 110.00(2) 1_555 1_555 1_555 yes
H(3C) C(3) H(3B) 110.26(2) 1_555 1_555 1_555 yes
H(3A) C(3) H(3B) 104.25(2) 1_555 1_555 1_555 yes
N(2) C(4) H(4A) 107.62(2) 1_555 1_555 1_555 yes
N(2) C(4) H(4C) 111.13(2) 1_555 1_555 1_555 yes
N(2) C(4) H(4B) 110.92(2) 1_555 1_555 1_555 yes
H(4A) C(4) H(4C) 107.962(19) 1_555 1_555 1_555 yes
H(4A) C(4) H(4B) 107.80(2) 1_555 1_555 1_555 yes
H(4C) C(4) H(4B) 111.24(2) 1_555 1_555 1_555 yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(1) C(1) 1.2896(3) 1_555 1_555 yes
O(2) C(1) 1.2275(3) 1_555 1_555 yes
O(3) C(2) 1.2769(3) 1_555 1_555 yes
N(1) C(2) 1.3397(3) 1_555 1_555 yes
N(1) C(3) 1.4532(4) 1_555 1_555 yes
N(1) H(1A) 1.0060(2) 1_555 1_555 yes
N(2) C(2) 1.3398(3) 1_555 1_555 yes
N(2) C(4) 1.4495(3) 1_555 1_555 yes
N(2) H(2A) 1.0140(2) 1_555 1_555 yes
C(3) H(3C) 1.0810(2) 1_555 1_555 yes
C(3) H(3A) 1.0680(3) 1_555 1_555 yes
C(3) H(3B) 1.0960(2) 1_555 1_555 yes
C(4) H(4A) 1.0900(2) 1_555 1_555 yes
C(4) H(4C) 1.0900(2) 1_555 1_555 yes
C(4) H(4B) 1.0890(2) 1_555 1_555 yes
loop_
_atom_local_dummy_label
_atom_local_dummy_fract_x
_atom_local_dummy_fract_y
_atom_local_dummy_fract_z
DUM0 0 0 0
