#------------------------------------------------------------------------------
#$Date: 2024-04-06 01:43:14 +0200 (Sat 06 de Apr de 2024) $
#$Revision: 291121 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/30/2023028.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2023028
loop_
_publ_author_name
'Mondal, Bipul'
_publ_section_title
;
 Crystal structure of di-ethyl-ammonium
 dioxido{Z)-N-[(pyri-din-2-yl)car-bon-yl-azan-idyl]pyri-dine-2-car-box-imid-ato}vana-date(1-)
 monohydrate.
;
_journal_coeditor_code           EV2002
_journal_issue                   'Pt 3'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              277
_journal_page_last               280
_journal_paper_doi               10.1107/S2056989024001166
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          '(C4 H12 N) [V (C12 H8 N4 O2) O2] , H2 O'
_chemical_formula_moiety         'C12 H8 N4 O4 V, C4 H12 N, H2 O'
_chemical_formula_sum            'C16 H22 N5 O5 V'
_chemical_formula_weight         415.32
_chemical_name_systematic
;Diethylammonium
dioxido{Z)-N-[(pyridin-2-yl)carbonylazanidyl]pyridine-2-carboximidato}vanadate(1-) monohydrate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                105.609(2)
_cell_angle_beta                 101.103(2)
_cell_angle_gamma                96.253(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6850(4)
_cell_length_b                   9.4135(4)
_cell_length_c                   13.9147(7)
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    298
_cell_measurement_theta_max      30.19
_cell_measurement_theta_min      2.28
_cell_volume                     937.50(8)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX2 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT V8.40B (Bruker, 2016)
;
_computing_molecular_graphics
;
Olex2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018/2 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Quest with Photon II area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            61285
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.129
_diffrn_reflns_theta_min         2.280
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.567
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_correction_T_min  0.6702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.392
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         5048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0450P)²+0.4439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1096
_reflns_number_gt                3852
_reflns_number_total             5048
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ev2002sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2023028.cif.'
_cod_database_code               2023028
_cod_database_fobs_code          2023028
_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, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
V V1 0.58085(4) 0.29537(3) 0.78356(3) 0.03307(10) Uani d 1 . .
N N4 0.0021(2) -0.1100(2) 0.63830(14) 0.0431(4) Uani d 1 . .
O O2 0.5724(2) 0.42364(17) 0.88516(12) 0.0518(4) Uani d 1 . .
O O3 0.32784(18) 0.22542(14) 0.71551(11) 0.0394(3) Uani d 1 . .
N N3 0.36076(19) -0.00629(16) 0.73136(13) 0.0332(3) Uani d 1 . .
C C1 0.9836(3) 0.3489(2) 0.88556(17) 0.0419(5) Uani d 1 . .
H H1 0.979921 0.446045 0.882458 0.050 Uiso calc 1 . .
O O1 0.6564(2) 0.36927(18) 0.70301(13) 0.0528(4) Uani d 1 . .
C C2 1.1439(3) 0.3148(3) 0.92898(18) 0.0487(5) Uani d 1 . .
H H2 1.246761 0.387685 0.955215 0.058 Uiso calc 1 . .
O O5 0.8727(2) 0.6487(2) 0.7639(2) 0.0755(6) Uani d 1 . .
H H5C 0.799539 0.566441 0.738019 0.113 Uiso d 1 . .
H H5D 0.806183 0.714430 0.777364 0.113 Uiso d 1 . .
N N2 0.53498(19) 0.07461(16) 0.77552(12) 0.0316(3) Uani d 1 . .
C C4 0.9945(3) 0.0640(2) 0.89249(17) 0.0415(4) Uani d 1 . .
H H4 0.996177 -0.034329 0.893312 0.050 Uiso calc 1 . .
N N5 1.2242(3) 0.6901(2) 0.72745(16) 0.0484(5) Uani d 1 . .
H H5A 1.107(4) 0.694(3) 0.740(2) 0.058 Uiso d 1 A 1
H H5B 1.276(4) 0.777(3) 0.732(2) 0.058 Uiso d 1 B 2
C C3 1.1493(3) 0.1707(3) 0.93290(18) 0.0493(5) Uani d 1 . .
H H3 1.256060 0.145211 0.962437 0.059 Uiso calc 1 . .
O O4 0.64803(19) -0.13258(15) 0.80366(14) 0.0497(4) Uani d 1 . .
N N1 0.8323(2) 0.24697(17) 0.84751(12) 0.0325(3) Uani d 1 . .
C C5 0.8380(2) 0.1063(2) 0.85105(14) 0.0313(4) Uani d 1 . .
C C7 0.2627(2) 0.08519(19) 0.70259(14) 0.0311(4) Uani d 1 . .
C C6 0.6610(2) 0.00098(19) 0.80739(15) 0.0330(4) Uani d 1 . .
C C14 1.3191(3) 0.6392(3) 0.8113(2) 0.0598(7) Uani d 1 . .
H H14A 1.442548 0.635076 0.805965 0.072 Uiso calc 1 . .
H H14B 1.261482 0.539255 0.805202 0.072 Uiso calc 1 . .
C C13 1.3170(4) 0.7421(4) 0.9123(2) 0.0828(10) Uani d 1 . .
H H13A 1.371411 0.841452 0.917594 0.124 Uiso calc 1 . .
H H13B 1.383288 0.709304 0.965860 0.124 Uiso calc 1 . .
H H13C 1.194956 0.742057 0.918946 0.124 Uiso calc 1 . .
C C15A 1.1933(5) 0.5973(5) 0.6175(4) 0.0527(10) Uani d 0.7 C 1
H H15A 1.112883 0.639100 0.573984 0.063 Uiso calc 0.7 C 1
H H15B 1.137207 0.496051 0.609451 0.063 Uiso calc 0.7 C 1
C C16A 1.3721(7) 0.5944(7) 0.5852(5) 0.0695(13) Uani d 0.7 C 1
H H16A 1.349650 0.557036 0.511873 0.104 Uiso calc 0.7 C 1
H H16B 1.438875 0.530498 0.615382 0.104 Uiso calc 0.7 C 1
H H16C 1.440214 0.693958 0.608190 0.104 Uiso calc 0.7 C 1
C C8 0.0699(2) 0.0330(2) 0.65164(14) 0.0326(4) Uani d 1 . .
C C9 -0.0329(3) 0.1301(2) 0.61863(16) 0.0421(5) Uani d 1 . .
H H9 0.017119 0.229460 0.630326 0.050 Uiso calc 1 . .
C C10 -0.2108(3) 0.0772(3) 0.56808(19) 0.0534(6) Uani d 1 . .
H H10 -0.282243 0.140321 0.544890 0.064 Uiso calc 1 . .
C C11 -0.2801(3) -0.0687(3) 0.55262(19) 0.0554(6) Uani d 1 . .
H H11 -0.398965 -0.107782 0.517707 0.067 Uiso calc 1 . .
C C12 -0.1699(3) -0.1567(3) 0.58996(19) 0.0526(6) Uani d 1 . .
H H12 -0.219043 -0.255526 0.580788 0.063 Uiso calc 1 . .
C C15B 1.279(3) 0.5710(13) 0.6404(12) 0.102(6) Uani d 0.3 C 2
H H15C 1.399256 0.553432 0.665826 0.123 Uiso calc 0.3 C 2
H H15D 1.196845 0.477106 0.621828 0.123 Uiso calc 0.3 C 2
C C16B 1.276(3) 0.6182(19) 0.5559(13) 0.116(6) Uani d 0.3 C 2
H H16D 1.270778 0.533969 0.497547 0.173 Uiso calc 0.3 C 2
H H16E 1.383543 0.688974 0.567037 0.173 Uiso calc 0.3 C 2
H H16F 1.172786 0.664919 0.543386 0.173 Uiso calc 0.3 C 2
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'
V V 0.3005 0.5294 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 V1 O3 . . 102.55(7) ?
O2 V1 O1 . . 110.64(9) ?
O2 V1 N2 . . 121.01(8) ?
O2 V1 N1 . . 95.14(7) ?
O3 V1 N2 . . 74.82(5) ?
O3 V1 N1 . . 148.99(6) ?
O1 V1 O3 . . 102.22(7) ?
O1 V1 N2 . . 127.77(8) ?
O1 V1 N1 . . 94.92(7) ?
N2 V1 N1 . . 74.24(6) ?
C12 N4 C8 . . 116.92(18) ?
C7 O3 V1 . . 117.29(11) ?
C7 N3 N2 . . 106.98(14) ?
N1 C1 C2 . . 122.3(2) ?
C1 C2 C3 . . 118.8(2) ?
N3 N2 V1 . . 118.33(10) ?
C6 N2 V1 . . 124.19(12) ?
C6 N2 N3 . . 117.46(14) ?
C5 C4 C3 . . 118.71(19) ?
C14 N5 C15A . . 120.9(2) ?
C14 N5 C15B . . 94.6(6) ?
C2 C3 C4 . . 119.43(19) ?
C1 N1 V1 . . 123.69(13) ?
C1 N1 C5 . . 118.88(16) ?
C5 N1 V1 . . 117.43(12) ?
C4 C5 C6 . . 123.33(17) ?
N1 C5 C4 . . 121.92(17) ?
N1 C5 C6 . . 114.75(15) ?
O3 C7 C8 . . 117.03(15) ?
N3 C7 O3 . . 122.55(16) ?
N3 C7 C8 . . 120.41(16) ?
N2 C6 C5 . . 109.38(15) ?
O4 C6 N2 . . 129.15(17) ?
O4 C6 C5 . . 121.47(16) ?
N5 C14 C13 . . 110.7(2) ?
N5 C15A C16A . . 109.9(3) ?
N4 C8 C7 . . 117.44(16) ?
N4 C8 C9 . . 122.41(18) ?
C9 C8 C7 . . 120.14(17) ?
C10 C9 C8 . . 119.0(2) ?
C11 C10 C9 . . 119.1(2) ?
C10 C11 C12 . . 118.2(2) ?
N4 C12 C11 . . 124.4(2) ?
C16B C15B N5 . . 111.2(11) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
V1 O2 . 1.6107(15) y
V1 O3 . 1.9461(14) y
V1 O1 . 1.6310(16) y
V1 N2 . 2.0385(15) y
V1 N1 . 2.1170(15) y
N4 C8 . 1.340(2) ?
N4 C12 . 1.329(3) ?
O3 C7 . 1.311(2) ?
N3 N2 . 1.400(2) ?
N3 C7 . 1.296(2) ?
C1 C2 . 1.375(3) ?
C1 N1 . 1.342(2) ?
C2 C3 . 1.377(3) ?
N2 C6 . 1.327(2) ?
C4 C3 . 1.385(3) ?
C4 C5 . 1.378(3) ?
N5 C14 . 1.473(3) ?
N5 C15A . 1.502(5) ?
N5 C15B . 1.573(16) ?
O4 C6 . 1.237(2) ?
N1 C5 . 1.343(2) ?
C5 C6 . 1.506(2) ?
C7 C8 . 1.480(2) ?
C14 C13 . 1.481(4) ?
C15A C16A . 1.526(7) ?
C8 C9 . 1.383(3) ?
C9 C10 . 1.380(3) ?
C10 C11 . 1.362(4) ?
C11 C12 . 1.374(3) ?
C15B C16B . 1.36(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N5 H5A O5 . 0.95(3) 1.92(3) 2.848(3) 165(3)
N5 H5B N3 1_665 0.85(3) 2.08(3) 2.918(3) 171(3)
O5 H5C O1 . 0.85 1.94 2.776(3) 169
O5 H5D O4 1_565 0.85 1.99 2.838(2) 178
C2 H2 O2 2_767 0.93 2.48 3.277(3) 143
C14 H14A O4 1_665 0.97 2.57 3.172(3) 121
C15A H15A N4 1_665 0.97 2.59 3.233(5) 124
