#------------------------------------------------------------------------------
#$Date: 2019-12-26 22:12:37 +0200 (Thu, 26 Dec 2019) $
#$Revision: 246155 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/18/2311890.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_2311890
loop_
_publ_author_name
'Castro, Miguel'
'Falvello, Larry R.'
'Forcén-Vázquez, Elena'
'Guerra, Pablo'
'Al-Kenany, Nuha A'
'Martínez, Gema'
'Tomás, Milagros'
_publ_section_title
;
 A phase transition caught in mid-course: independent and concomitant
 analyses of the monoclinic and triclinic structures of
 (ⁿBu₄N)[Co(orotate)₂(bipy)]·3H₂O.
;
_journal_coeditor_code           SK3662
_journal_issue                   'Pt 9'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              731
_journal_page_last               742
_journal_paper_doi               10.1107/S2053229617010841
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac
'(C16 H36 N) [Co (C5 H2 N2 O4)2 (C10 H8 N2)], 3H2 O'
_chemical_formula_moiety         'C16 H36 N +, C20 H12 Co N6 O8 -, 3(H2 O)'
_chemical_formula_sum            'C36 H54 Co N7 O11'
_chemical_formula_weight         819.79
_chemical_name_systematic
;
Tetra-n-butylammonium
(2,2'-bipyridine-κ²N,N')bis(2,4-dioxo-1,2,3,4-\
tetrahydropyrimidin-1-ide-6-carboxylato-κN¹)cobalt(III) trihydrate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 102.669(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.1679(12)
_cell_length_b                   9.3413(9)
_cell_length_c                   16.3388(14)
_cell_measurement_reflns_used    2532
_cell_measurement_temperature    277.0(10)
_cell_measurement_theta_max      27.536
_cell_measurement_theta_min      4.234
_cell_volume                     1960.8(3)
_computing_cell_refinement
;
CrysAlis PRO Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis PRO Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis PRO Oxford Diffraction, 2009)
;
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1996)'
_computing_publication_material  'SHELXL2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_structure_solution
;
SIR92 (Altomare et al., 1994)
;
_diffrn_ambient_temperature      277.0(10)
_diffrn_detector_area_resol_mean 16.0655
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measurement_device_type
'Oxford Diffraction KM-4/Xcalibur with a Sapphire3 detector'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10924
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.863
_diffrn_reflns_theta_min         3.815
_exptl_absorpt_coefficient_mu    0.505
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       plate
_exptl_crystal_F_000             868
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.309
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4564
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0549
_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)+(0.0350P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1100
_reflns_number_gt                2511
_reflns_number_total             4564
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sk3662sup1.cif
_cod_data_source_block           2a
_cod_original_sg_symbol_H-M      'P 2/n'
_cod_database_code               2311890
_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   0.915
_shelx_estimated_absorpt_t_max   0.970
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'
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
Co Co1 0.2500 0.33659(6) 0.7500 0.03719(18) Uani d 1
N N1 0.24864(16) 0.3156(3) 0.86825(12) 0.0380(6) Uani d 1
C C2 0.1864(2) 0.3821(3) 0.91432(17) 0.0413(7) Uani d 1
O O2 0.12172(16) 0.4736(3) 0.88636(12) 0.0612(7) Uani d 1
N N3 0.19950(17) 0.3371(3) 0.99698(12) 0.0421(6) Uani d 1
H H3 0.1595 0.3767 1.0256 0.051 Uiso calc 1
C C4 0.2682(2) 0.2375(3) 1.03861(17) 0.0427(7) Uani d 1
O O4 0.27290(14) 0.2103(2) 1.11331(11) 0.0511(6) Uani d 1
C C5 0.3298(2) 0.1719(3) 0.98680(15) 0.0414(7) Uani d 1
H H5 0.3784 0.1018 1.0086 0.050 Uiso calc 1
C C6 0.3167(2) 0.2128(3) 0.90651(16) 0.0365(7) Uani d 1
C C7 0.3769(2) 0.1442(3) 0.84799(17) 0.0400(7) Uani d 1
O O7 0.35450(14) 0.1945(2) 0.77301(10) 0.0434(5) Uani d 1
O O8 0.44135(17) 0.0516(2) 0.87219(12) 0.0561(6) Uani d 1
N N9 0.34807(17) 0.4915(3) 0.77553(12) 0.0366(6) Uani d 1
C C10 0.4511(2) 0.4772(4) 0.80157(17) 0.0489(8) Uani d 1
H H10 0.4798 0.3858 0.8076 0.059 Uiso calc 1
C C11 0.5161(2) 0.5946(4) 0.81986(18) 0.0528(9) Uani d 1
H H11 0.5875 0.5823 0.8386 0.063 Uiso calc 1
C C12 0.4739(3) 0.7293(4) 0.8099(2) 0.0601(9) Uani d 1
H H12 0.5162 0.8097 0.8221 0.072 Uiso calc 1
C C13 0.3682(3) 0.7438(4) 0.78174(19) 0.0563(9) Uani d 1
H H13 0.3383 0.8344 0.7742 0.068 Uiso calc 1
C C14 0.3064(2) 0.6228(3) 0.76465(16) 0.0409(7) Uani d 1
N N15 0.7500 0.1433(4) 0.7500 0.0547(10) Uani d 1
C C16 0.8409(2) 0.0458(3) 0.78462(18) 0.0544(9) Uani d 1
H H16A 0.8591 -0.0049 0.7380 0.065 Uiso calc 1
H H16B 0.8182 -0.0250 0.8202 0.065 Uiso calc 1
C C17 0.9390(3) 0.1172(4) 0.8349(2) 0.0698(10) Uani d 1
H H17A 0.9239 0.1588 0.8853 0.084 Uiso calc 1
H H17B 0.9590 0.1943 0.8018 0.084 Uiso calc 1
C C18 1.0314(3) 0.0119(4) 0.8599(2) 0.0846(12) Uani d 1
H H18A 1.0553 -0.0142 0.8098 0.102 Uiso calc 1
H H18B 1.0881 0.0607 0.8973 0.102 Uiso calc 1
C C19 1.0072(3) -0.1188(5) 0.9008(3) 0.1034(15) Uani d 1
H H19A 0.9792 -0.0943 0.9485 0.155 Uiso calc 1
H H19B 1.0695 -0.1741 0.9189 0.155 Uiso calc 1
H H19C 0.9570 -0.1739 0.8619 0.155 Uiso calc 1
C C20 0.7270(3) 0.2411(4) 0.8175(2) 0.0766(12) Uani d 1
H H20A 0.7868 0.3027 0.8366 0.092 Uiso calc 1
H H20B 0.6687 0.3019 0.7927 0.092 Uiso calc 1
C C21 0.7021(3) 0.1679(5) 0.8927(2) 0.0844(13) Uani d 1
H H21A 0.7531 0.0939 0.9129 0.101 Uiso calc 1
H H21B 0.6339 0.1236 0.8777 0.101 Uiso calc 1
C C22 0.7039(4) 0.2822(7) 0.9619(4) 0.162(3) Uani d 1
H H22A 0.7758 0.2897 0.9922 0.194 Uiso calc 1
H H22B 0.6869 0.3726 0.9329 0.194 Uiso calc 1
C C23 0.6534(6) 0.2771(9) 1.0134(4) 0.242(5) Uani d 1
H H23A 0.5815 0.2923 0.9874 0.363 Uiso calc 1
H H23B 0.6763 0.3500 1.0547 0.363 Uiso calc 1
H H23C 0.6616 0.1848 1.0399 0.363 Uiso calc 1
O O1W 0.5898(3) 0.5125(3) 0.6088(2) 0.0689(8) Uani d 1
H H1WA 0.529(4) 0.515(6) 0.597(3) 0.14(2) Uiso d 1
H H1WB 0.613(3) 0.558(5) 0.653(3) 0.12(2) Uiso d 1
O O2W 0.7500 0.6271(4) 0.7500 0.0640(11) Uani d 1
H H2WA 0.743(3) 0.674(4) 0.7910(19) 0.089(13) Uiso d 1
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'
Co Co 0.3494 0.9721 '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
O7 Co1 O7 2_556 . 90.76(12)
O7 Co1 N9 2_556 . 175.38(9)
O7 Co1 N9 . . 93.45(9)
O7 Co1 N9 2_556 2_556 93.45(9)
O7 Co1 N9 . 2_556 175.38(9)
N9 Co1 N9 . 2_556 82.42(14)
O7 Co1 N1 2_556 2_556 84.07(8)
O7 Co1 N1 . 2_556 87.83(8)
N9 Co1 N1 . 2_556 97.99(9)
N9 Co1 N1 2_556 2_556 90.70(9)
O7 Co1 N1 2_556 . 87.83(8)
O7 Co1 N1 . . 84.07(8)
N9 Co1 N1 . . 90.70(9)
N9 Co1 N1 2_556 . 97.99(9)
N1 Co1 N1 2_556 . 168.46(15)
C6 N1 C2 . . 118.4(2)
C6 N1 Co1 . . 112.13(16)
C2 N1 Co1 . . 129.3(2)
O2 C2 N1 . . 124.1(2)
O2 C2 N3 . . 120.2(2)
N1 C2 N3 . . 115.7(3)
C4 N3 C2 . . 128.0(2)
C4 N3 H3 . . 116.0
C2 N3 H3 . . 116.0
O4 C4 N3 . . 121.0(2)
O4 C4 C5 . . 125.8(3)
N3 C4 C5 . . 113.3(2)
C6 C5 C4 . . 119.2(3)
C6 C5 H5 . . 120.4
C4 C5 H5 . . 120.4
C5 C6 N1 . . 125.3(2)
C5 C6 C7 . . 121.7(3)
N1 C6 C7 . . 113.0(2)
O8 C7 O7 . . 124.7(2)
O8 C7 C6 . . 121.4(2)
O7 C7 C6 . . 113.9(3)
C7 O7 Co1 . . 116.87(17)
C10 N9 C14 . . 119.4(3)
C10 N9 Co1 . . 125.5(2)
C14 N9 Co1 . . 115.09(19)
N9 C10 C11 . . 121.8(3)
N9 C10 H10 . . 119.1
C11 C10 H10 . . 119.1
C12 C11 C10 . . 119.1(3)
C12 C11 H11 . . 120.4
C10 C11 H11 . . 120.4
C11 C12 C13 . . 119.0(3)
C11 C12 H12 . . 120.5
C13 C12 H12 . . 120.5
C12 C13 C14 . . 119.7(3)
C12 C13 H13 . . 120.2
C14 C13 H13 . . 120.2
N9 C14 C13 . . 121.0(3)
N9 C14 C14 . 2_556 113.70(16)
C13 C14 C14 . 2_556 125.31(19)
C16 N15 C16 2_656 . 105.9(3)
C16 N15 C20 2_656 . 111.55(18)
C16 N15 C20 . . 111.06(18)
C16 N15 C20 2_656 2_656 111.06(18)
C16 N15 C20 . 2_656 111.55(18)
C20 N15 C20 . 2_656 105.8(4)
N15 C16 C17 . . 116.5(3)
N15 C16 H16A . . 108.2
C17 C16 H16A . . 108.2
N15 C16 H16B . . 108.2
C17 C16 H16B . . 108.2
H16A C16 H16B . . 107.3
C16 C17 C18 . . 112.8(3)
C16 C17 H17A . . 109.0
C18 C17 H17A . . 109.0
C16 C17 H17B . . 109.0
C18 C17 H17B . . 109.0
H17A C17 H17B . . 107.8
C19 C18 C17 . . 114.5(3)
C19 C18 H18A . . 108.6
C17 C18 H18A . . 108.6
C19 C18 H18B . . 108.6
C17 C18 H18B . . 108.6
H18A C18 H18B . . 107.6
C18 C19 H19A . . 109.5
C18 C19 H19B . . 109.5
H19A C19 H19B . . 109.5
C18 C19 H19C . . 109.5
H19A C19 H19C . . 109.5
H19B C19 H19C . . 109.5
C21 C20 N15 . . 115.8(3)
C21 C20 H20A . . 108.3
N15 C20 H20A . . 108.3
C21 C20 H20B . . 108.3
N15 C20 H20B . . 108.3
H20A C20 H20B . . 107.4
C20 C21 C22 . . 108.1(4)
C20 C21 H21A . . 110.1
C22 C21 H21A . . 110.1
C20 C21 H21B . . 110.1
C22 C21 H21B . . 110.1
H21A C21 H21B . . 108.4
C23 C22 C21 . . 124.7(6)
C23 C22 H22A . . 106.1
C21 C22 H22A . . 106.1
C23 C22 H22B . . 106.1
C21 C22 H22B . . 106.1
H22A C22 H22B . . 106.3
C22 C23 H23A . . 109.5
C22 C23 H23B . . 109.5
H23A C23 H23B . . 109.5
C22 C23 H23C . . 109.5
H23A C23 H23C . . 109.5
H23B C23 H23C . . 109.5
H1WA O1W H1WB . . 110(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Co1 O7 2_556 1.8891(19)
Co1 O7 . 1.8891(18)
Co1 N9 . 1.923(2)
Co1 N9 2_556 1.923(2)
Co1 N1 2_556 1.9459(19)
Co1 N1 . 1.9459(19)
N1 C6 . 1.368(3)
N1 C2 . 1.376(3)
C2 O2 . 1.222(3)
C2 N3 . 1.389(3)
N3 C4 . 1.370(4)
N3 H3 . 0.8600
C4 O4 . 1.235(3)
C4 C5 . 1.432(4)
C5 C6 . 1.340(3)
C5 H5 . 0.9300
C6 C7 . 1.512(3)
C7 O8 . 1.216(3)
C7 O7 . 1.284(3)
N9 C10 . 1.336(3)
N9 C14 . 1.340(3)
C10 C11 . 1.383(4)
C10 H10 . 0.9300
C11 C12 . 1.371(4)
C11 H11 . 0.9300
C12 C13 . 1.373(4)
C12 H12 . 0.9300
C13 C14 . 1.385(4)
C13 H13 . 0.9300
C14 C14 2_556 1.457(6)
N15 C16 2_656 1.512(4)
N15 C16 . 1.512(4)
N15 C20 . 1.513(4)
N15 C20 2_656 1.513(4)
C16 C17 . 1.524(4)
C16 H16A . 0.9700
C16 H16B . 0.9700
C17 C18 . 1.548(5)
C17 H17A . 0.9700
C17 H17B . 0.9700
C18 C19 . 1.460(5)
C18 H18A . 0.9700
C18 H18B . 0.9700
C19 H19A . 0.9600
C19 H19B . 0.9600
C19 H19C . 0.9600
C20 C21 . 1.503(5)
C20 H20A . 0.9700
C20 H20B . 0.9700
C21 C22 . 1.552(5)
C21 H21A . 0.9700
C21 H21B . 0.9700
C22 C23 . 1.182(6)
C22 H22A . 0.9700
C22 H22B . 0.9700
C23 H23A . 0.9600
C23 H23B . 0.9600
C23 H23C . 0.9600
O1W H1WA . 0.78(5)
O1W H1WB . 0.84(5)
O2W H2WA . 0.83(3)
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
N3 H3 O1W 4_566 0.86 2.08 2.925(3) 168.9
O1W H1WA O2 2_556 0.78(5) 2.10(5) 2.828(4) 156(5)
O1W H1WB O2W . 0.84(5) 2.22(5) 2.964(4) 147(4)
O2W H2WA O4 3_667 0.83(3) 1.95(3) 2.772(3) 179(4)
C10 H10 O7 . 0.93 2.41 2.923(4) 114.4
C16 H16B O4 3_657 0.97 2.49 3.442(4) 167.9
C20 H20A O1W 2_656 0.97 2.58 3.525(5) 165.5
C21 H21B O8 . 0.97 2.61 3.546(4) 163.4
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C6 N1 C2 O2 . . -178.7(3)
Co1 N1 C2 O2 . . -3.1(4)
C6 N1 C2 N3 . . 0.1(4)
Co1 N1 C2 N3 . . 175.78(18)
O2 C2 N3 C4 . . -179.4(3)
N1 C2 N3 C4 . . 1.7(4)
C2 N3 C4 O4 . . 178.4(3)
C2 N3 C4 C5 . . -2.1(4)
O4 C4 C5 C6 . . -179.7(3)
N3 C4 C5 C6 . . 0.9(4)
C4 C5 C6 N1 . . 0.8(4)
C4 C5 C6 C7 . . -178.0(2)
C2 N1 C6 C5 . . -1.3(4)
Co1 N1 C6 C5 . . -177.7(2)
C2 N1 C6 C7 . . 177.6(2)
Co1 N1 C6 C7 . . 1.2(3)
C5 C6 C7 O8 . . -1.7(4)
N1 C6 C7 O8 . . 179.4(3)
C5 C6 C7 O7 . . 179.3(2)
N1 C6 C7 O7 . . 0.4(3)
O8 C7 O7 Co1 . . 179.1(2)
C6 C7 O7 Co1 . . -1.9(3)
O7 Co1 O7 C7 2_556 . -85.63(19)
N9 Co1 O7 C7 . . 92.5(2)
N1 Co1 O7 C7 2_556 . -169.7(2)
N1 Co1 O7 C7 . . 2.1(2)
C14 N9 C10 C11 . . 1.7(4)
Co1 N9 C10 C11 . . -178.97(19)
N9 C10 C11 C12 . . -0.9(4)
C10 C11 C12 C13 . . -0.3(5)
C11 C12 C13 C14 . . 0.6(5)
C10 N9 C14 C13 . . -1.4(4)
Co1 N9 C14 C13 . . 179.2(2)
C10 N9 C14 C14 . 2_556 179.4(2)
Co1 N9 C14 C14 . 2_556 0.1(4)
C12 C13 C14 N9 . . 0.3(4)
C12 C13 C14 C14 . 2_556 179.3(3)
C16 N15 C16 C17 2_656 . -171.4(3)
C20 N15 C16 C17 . . -50.1(3)
C20 N15 C16 C17 2_656 . 67.6(3)
N15 C16 C17 C18 . . -174.0(2)
C16 C17 C18 C19 . . -51.3(4)
C16 N15 C20 C21 2_656 . 59.5(4)
C16 N15 C20 C21 . . -58.5(4)
C20 N15 C20 C21 2_656 . -179.7(4)
N15 C20 C21 C22 . . 168.3(3)
C20 C21 C22 C23 . . 150.6(8)
