#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:08:05 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180530 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/99/7219985.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_7219985
loop_
_publ_author_name
'Schmidtmann, Marc'
'Middlemiss, Derek S.'
'Wilson, Chick C.'
_publ_section_title
;
 Isotopomeric polymorphism in a “doubly-polymorphic”
 multi-component molecular crystal
;
_journal_issue                   28
_journal_name_full               CrystEngComm
_journal_page_first              5273
_journal_paper_doi               10.1039/C5CE00123D
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         '2[DC6H4D2N2O]+ [C2O4]2'
_chemical_formula_sum            'C14 H8 D6 N4 O6'
_chemical_formula_weight         340.33
_chemical_name_systematic        'bis(isonicotinamide)-d-oxalic acid Form I'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-01-16 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                98.262(4)
_cell_angle_beta                 90.019(4)
_cell_angle_gamma                91.709(5)
_cell_formula_units_Z            1
_cell_length_a                   3.7233(3)
_cell_length_b                   7.4294(5)
_cell_length_c                   12.3158(10)
_cell_measurement_reflns_used    5440
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.29
_cell_measurement_theta_min      2.77
_cell_volume                     336.99(4)
_computing_cell_refinement       'Bruker AXS SAINT V7.34A'
_computing_data_collection       'Bruker AXS X8 Apex2'
_computing_data_reduction        'Bruker AXS SAINT V7.34A'
_computing_molecular_graphics    'Bruker AXS XP'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10173
_diffrn_reflns_theta_full        33.99
_diffrn_reflns_theta_max         33.99
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             174
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: D2O'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2744
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0600P)²+0.0400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                2505
_reflns_number_total             2744
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ce00123d2.cif
_cod_data_source_block           doxaiso
_cod_depositor_comments
'Adding full bibliography for 7219985--7219986.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7219985
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
O1 O 0.92658(16) 0.22578(7) 0.48418(4) 0.01706(12) Uani 1 1 d
O2 O 1.07184(15) -0.00976(7) 0.35855(4) 0.01486(11) Uani 1 1 d
O3 O 0.19641(15) 0.77292(7) 0.99444(4) 0.01601(12) Uani 1 1 d
N1 N 0.62643(16) 0.34963(8) 0.67990(5) 0.01449(12) Uani 1 1 d
D1 D 0.720(5) 0.247(3) 0.6301(16) 0.068(5) Uiso 1 1 d
N2 N 0.08291(16) 0.92982(7) 0.85367(4) 0.01285(11) Uani 1 1 d
C1 C 0.99897(17) 0.06335(8) 0.45467(5) 0.01112(12) Uani 1 1 d
C2 C 0.50076(18) 0.31948(9) 0.77792(6) 0.01418(13) Uani 1 1 d
H2 H 0.523(4) 0.1983(17) 0.7951(10) 0.025(3) Uiso 1 1 d
C3 C 0.35609(17) 0.46001(8) 0.84847(5) 0.01187(12) Uani 1 1 d
H3 H 0.271(4) 0.4349(19) 0.9190(11) 0.030(3) Uiso 1 1 d
C4 C 0.34116(16) 0.63174(8) 0.81578(5) 0.00964(11) Uani 1 1 d
C5 C 0.47212(18) 0.65815(9) 0.71315(5) 0.01197(12) Uani 1 1 d
H4 H 0.475(3) 0.7726(17) 0.6869(10) 0.022(3) Uiso 1 1 d
C6 C 0.61692(18) 0.51276(9) 0.64636(5) 0.01412(12) Uani 1 1 d
H5 H 0.726(4) 0.5221(18) 0.5777(11) 0.030(3) Uiso 1 1 d
C7 C 0.19788(17) 0.78590(8) 0.89535(5) 0.01058(12) Uani 1 1 d
D6 D -0.013(4) 1.0244(18) 0.9051(11) 0.030(3) Uiso 1 1 d
D7 D 0.055(4) 0.9289(18) 0.7811(11) 0.025(3) Uiso 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0291(3) 0.0107(2) 0.0118(2) 0.00160(16) 0.00407(18) 0.00741(18)
O2 0.0237(3) 0.0128(2) 0.0082(2) 0.00104(15) 0.00321(16) 0.00501(17)
O3 0.0256(3) 0.0144(2) 0.0084(2) 0.00144(16) 0.00156(17) 0.00723(18)
N1 0.0125(2) 0.0138(2) 0.0151(3) -0.00499(19) 0.00029(18) 0.00265(18)
N2 0.0196(3) 0.0097(2) 0.0095(2) 0.00104(17) 0.00038(18) 0.00509(18)
C1 0.0141(3) 0.0108(2) 0.0086(2) 0.00119(18) 0.00139(18) 0.00324(19)
C2 0.0148(3) 0.0097(2) 0.0173(3) -0.0007(2) -0.0003(2) 0.00225(19)
C3 0.0141(3) 0.0095(2) 0.0121(3) 0.00162(19) 0.00069(19) 0.00215(18)
C4 0.0111(2) 0.0091(2) 0.0087(2) 0.00059(17) 0.00009(17) 0.00183(17)
C5 0.0141(3) 0.0126(2) 0.0091(2) 0.00086(19) 0.00108(19) 0.00160(19)
C6 0.0141(3) 0.0173(3) 0.0100(2) -0.0017(2) 0.00164(19) 0.0016(2)
C7 0.0132(3) 0.0090(2) 0.0094(2) 0.00037(18) 0.00063(18) 0.00256(18)
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'
D D 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_3
C6 N1 C2 122.40(6) .
C6 N1 D1 118.9(11) .
C2 N1 D1 118.6(11) .
D7 N2 D6 120.9(12) .
D7 N2 C7 122.1(9) .
D6 N2 C7 115.9(8) .
O1 C1 O2 126.64(6) .
O1 C1 C1 117.04(7) 2_756
O2 C1 C1 116.32(7) 2_756
H2 C2 N1 116.3(8) .
H2 C2 C3 123.8(8) .
N1 C2 C3 119.96(6) .
H3 C3 C2 118.2(8) .
H3 C3 C4 122.7(8) .
C2 C3 C4 119.05(6) .
C5 C4 C3 119.52(6) .
C5 C4 C7 121.85(5) .
C3 C4 C7 118.57(5) .
H4 C5 C6 117.6(8) .
H4 C5 C4 123.5(8) .
C6 C5 C4 118.88(6) .
H5 C6 N1 116.0(8) .
H5 C6 C5 123.7(8) .
N1 C6 C5 120.19(6) .
O3 C7 N2 124.02(6) .
O3 C7 C4 118.85(5) .
N2 C7 C4 117.13(5) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2468(8) .
O2 C1 1.2626(8) .
O3 C7 1.2378(7) .
N1 C6 1.3369(9) .
N1 C2 1.3410(9) .
N1 D1 0.98(2) .
N2 D7 0.898(13) .
N2 D6 0.953(14) .
N2 C7 1.3322(8) .
C1 C1 1.5605(12) 2_756
C2 H2 0.960(13) .
C2 C3 1.3814(9) .
C3 H3 0.967(13) .
C3 C4 1.3946(8) .
C4 C5 1.3928(8) .
C4 C7 1.5070(8) .
C5 H4 0.952(12) .
C5 C6 1.3833(9) .
C6 H5 0.948(14) .
