#------------------------------------------------------------------------------
#$Date: 2020-10-06 09:10:49 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257243 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/71/7127167.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_7127167
loop_
_publ_author_name
'Prodius, Denis'
'Klocke, Matthew'
'Smetana, Volodymyr'
'Alammar, Tarek'
'Perez Garcia, Marilu'
'Windus, Theresa L.'
'Nlebedim, Ikenna C.'
'Mudring, Anja-Verena'
_publ_section_title
;
 Rationally designed rare earth separation by selective oxalate
 solubilization.
;
_journal_issue                   77
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11386
_journal_page_last               11389
_journal_paper_doi               10.1039/d0cc02270e
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C4 H2 O8, 2(C4 H7 N2), 2(H2 O)'
_chemical_formula_sum            'C12 H20 N4 O10'
_chemical_formula_weight         380.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_audit_creation_date             2016-04-08
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2019-02-19 deposited with the CCDC.	2020-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.2700(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.8129(2)
_cell_length_b                   10.3804(2)
_cell_length_c                   6.9487(1)
_cell_measurement_reflns_used    4353
_cell_measurement_temperature    173
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.63
_cell_volume                     838.42(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      172.98
_diffrn_measured_fraction_theta_full 0.9628
_diffrn_measured_fraction_theta_max 0.9616
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            21310
_diffrn_reflns_theta_full        29.8826
_diffrn_reflns_theta_max         29.88
_diffrn_reflns_theta_min         1.75
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.5063
_exptl_crystal_description       'irregular fragment'
_exptl_crystal_F_000             400.2908
_refine_diff_density_max         0.6045
_refine_diff_density_min         -0.5442
_refine_diff_density_rms         0.1045
_refine_ls_d_res_high            0.7133
_refine_ls_d_res_low             11.6236
_refine_ls_goodness_of_fit_ref   1.0609
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    10
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2331
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0609
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0542
_refine_ls_shift/su_max          0.0038
_refine_ls_shift/su_mean         0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0847P)²+0.4108P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1407
_refine_ls_wR_factor_ref         0.1632
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                1626
_reflns_number_total             2331
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d0cc02270e2.cif
_cod_data_source_block           eimox2co
_cod_depositor_comments
'Adding full bibliography for 7127165--7127177.cif.'
_cod_original_cell_volume        838.42(3)
_cod_database_code               7127167
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Me refined with riding coordinates:
 C13(H13a,H13b,H13c)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C12(H12)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-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_refinement_flags_posn
O1 O 0.00100(11) 0.32647(12) 0.2179(2) 0.0245(3) Uani 1.000000 .
O2 O 0.17000(12) 0.32652(13) 0.4225(2) 0.0275(3) Uani 1.000000 .
O3 O 0.17521(11) 0.06448(13) 0.3878(2) 0.0277(4) Uani 1.000000 .
O4 O -0.01060(12) 0.07145(13) 0.2492(2) 0.0281(4) Uani 1.000000 .
N1 N -0.33965(13) 0.11085(15) -0.1348(2) 0.0210(4) Uani 1.000000 .
C6 C 0.08684(15) 0.27238(18) 0.3217(2) 0.0188(4) Uani 1.000000 .
N2 N -0.20022(14) 0.23536(17) -0.0078(2) 0.0245(4) Uani 1.000000 .
C8 C 0.08846(15) 0.12332(18) 0.3224(2) 0.0193(4) Uani 1.000000 .
C9 C -0.37761(16) 0.23620(19) -0.1689(3) 0.0229(4) Uani 1.000000 .
H9 H -0.45123(16) 0.26269(19) -0.2355(3) 0.0275(5) Uiso 1.000000 R
O1W O 0.35408(14) 0.15994(18) 0.6970(3) 0.0399(4) Uani 1.000000 .
C11 C -0.28964(17) 0.3138(2) -0.0892(3) 0.0246(4) Uani 1.000000 .
H11 H -0.28972(17) 0.4054(2) -0.0895(3) 0.0295(5) Uiso 1.000000 R
C12 C -0.23187(15) 0.11368(19) -0.0374(3) 0.0230(4) Uani 1.000000 .
H12 H -0.18548(15) 0.04058(19) 0.0039(3) 0.0276(5) Uiso 1.000000 R
C13 C -0.40351(18) -0.0060(2) -0.2037(3) 0.0307(5) Uani 1.000000 .
H13a H -0.48085(18) 0.0173(2) -0.2711(3) 0.0461(7) Uiso 1.000000 R
H13b H -0.36309(18) -0.0522(2) -0.2943(3) 0.0461(7) Uiso 1.000000 R
H13c H -0.40936(18) -0.0616(2) -0.0918(3) 0.0461(7) Uiso 1.000000 R
H2 H -0.127(2) 0.256(3) 0.062(3) 0.039(7) Uiso 1.000000 .
H1Wa H 0.299(3) 0.155(4) 0.601(6) 0.079(12) Uiso 1.000000 .
H1Wb H 0.309(3) 0.175(3) 0.792(5) 0.078(11) Uiso 1.000000 .
H H 0.004(3) 0.478(4) 0.239(5) 0.071(10) Uiso 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C12 N1 C9 108.53(16) . . ?
C13 N1 C9 126.26(16) . . ?
C13 N1 C12 125.11(16) . . ?
O2 C6 O1 126.61(17) . . ?
C8 C6 O1 116.96(15) . . ?
C8 C6 O2 116.43(16) . . ?
C12 N2 C11 109.09(16) . . ?
O4 C8 O3 125.34(18) . . ?
C6 C8 O3 121.01(16) . . ?
C6 C8 O4 113.65(15) . . ?
C11 C9 N1 106.75(16) . . ?
C9 C11 N2 107.06(17) . . ?
N2 C12 N1 108.55(17) . . ?
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
O1 C6 1.266(2) . ?
O2 C6 1.235(2) . ?
O3 C8 1.210(2) . ?
O4 C8 1.306(2) . ?
N1 C9 1.383(3) . ?
N1 C12 1.331(2) . ?
N1 C13 1.463(2) . ?
C6 C8 1.547(3) . ?
N2 C11 1.373(3) . ?
N2 C12 1.323(3) . ?
C9 C11 1.353(3) . ?
