#------------------------------------------------------------------------------
#$Date: 2016-11-16 04:34:20 +0200 (Wed, 16 Nov 2016) $
#$Revision: 188501 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/45/1544581.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_1544581
loop_
_publ_author_name
'Eltayeb, Naser Eltaher'
_publ_section_title
;
 Methyl 5-(4-hydroxyphenyl)-6-oxo-1,6-dihydropyrazine-2-carboxylate
 monohydrate
;
_journal_coeditor_code           HB4089
_journal_issue                   11
_journal_name_full               IUCrData
_journal_page_first              x161741
_journal_paper_doi               10.1107/S2414314616017417
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C12 H10 N2 O4, H2 O'
_chemical_formula_moiety         'C12 H10 N2 O4, H2 O'
_chemical_formula_sum            'C12 H12 N2 O5'
_chemical_formula_weight         264.24
_chemical_name_systematic
;
Methyl 5-(4-hydroxyphenyl)-6-oxo-1,6-dihydropyrazine-2-carboxylate 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'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                70.748(4)
_cell_angle_beta                 88.425(5)
_cell_angle_gamma                83.284(5)
_cell_formula_units_Z            2
_cell_length_a                   3.7072(3)
_cell_length_b                   11.4251(9)
_cell_length_c                   14.3713(13)
_cell_measurement_reflns_used    3588
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.31
_cell_measurement_theta_min      2.78
_cell_volume                     570.68(8)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_publication_material
;
APEX3 (Bruker, 2016) and PLATON (Spek, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Quest CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10223
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.783
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            Gold
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_description       Block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.341
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2091
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0486
_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)+(0.0581P)²+0.2621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1192
_reflns_number_gt                1556
_reflns_number_total             2091
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4089sup1.cif
_cod_data_source_block           I
_cod_database_code               1544581
_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
O O1 0.5384(5) 0.72898(15) -0.07116(12) 0.0208(4) Uani d 1
O O2 0.1695(4) 0.53640(13) 0.38440(11) 0.0185(4) Uani d 1
O O1W 0.2759(5) 0.93868(16) -0.21323(13) 0.0215(4) Uani d 1
O O3 0.0237(4) 0.68091(13) 0.65526(11) 0.0166(4) Uani d 1
O O4 0.2049(5) 0.87280(14) 0.61292(11) 0.0198(4) Uani d 1
N N1 0.1665(5) 0.65746(16) 0.48160(14) 0.0125(4) Uani d 1
N N2 0.4133(5) 0.84534(16) 0.32977(13) 0.0137(4) Uani d 1
C C1 0.3041(6) 0.84329(19) 0.13426(16) 0.0133(5) Uani d 1
H H1 0.2106 0.9183 0.1458 0.016 Uiso calc 1
C C2 0.3441(6) 0.84230(19) 0.03887(16) 0.0143(5) Uani d 1
H H2 0.2730 0.9157 -0.0149 0.017 Uiso calc 1
C C3 0.4887(6) 0.7337(2) 0.02149(16) 0.0145(5) Uani d 1
C C4 0.5883(6) 0.6262(2) 0.09990(16) 0.0154(5) Uani d 1
H H4 0.6897 0.5523 0.0879 0.018 Uiso calc 1
C C5 0.5405(6) 0.62616(19) 0.19544(16) 0.0147(5) Uani d 1
H H5 0.6038 0.5516 0.2489 0.018 Uiso calc 1
C C6 0.3997(6) 0.73496(19) 0.21435(16) 0.0123(5) Uani d 1
C C7 0.3548(6) 0.74126(19) 0.31435(16) 0.0128(5) Uani d 1
C C8 0.2279(6) 0.63618(19) 0.39424(16) 0.0115(5) Uani d 1
C C9 0.2278(6) 0.76628(19) 0.49603(16) 0.0121(5) Uani d 1
C C10 0.3518(6) 0.85802(19) 0.42030(16) 0.0137(5) Uani d 1
H H10 0.3972 0.9332 0.4303 0.016 Uiso calc 1
C C11 0.1537(6) 0.78086(19) 0.59361(16) 0.0137(5) Uani d 1
C C12 -0.0733(6) 0.6846(2) 0.75253(17) 0.0179(5) Uani d 1
H H12A -0.1903 0.6103 0.7886 0.027 Uiso calc 1
H H12B -0.2415 0.7596 0.7466 0.027 Uiso calc 1
H H12C 0.1462 0.6863 0.7883 0.027 Uiso calc 1
H H1N 0.070(8) 0.593(3) 0.531(2) 0.043(9) Uiso d 1
H H1O 0.451(9) 0.807(3) -0.114(2) 0.056(10) Uiso d 1
H H1W 0.224(9) 0.914(3) -0.261(3) 0.049(10) Uiso d 1
H H2W 0.388(9) 1.008(3) -0.238(2) 0.048(9) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 O1 H1O 106(2)
H1W O1W H2W 108(3)
C11 O3 C12 116.91(16)
C8 N1 C9 123.15(19)
C8 N1 H1N 115.4(18)
C9 N1 H1N 121.4(18)
C7 N2 C10 120.27(19)
C2 C1 C6 120.7(2)
C2 C1 H1 119.6
C6 C1 H1 119.6
C1 C2 C3 119.9(2)
C1 C2 H2 120.1
C3 C2 H2 120.1
O1 C3 C4 118.0(2)
O1 C3 C2 121.90(19)
C4 C3 C2 120.1(2)
C5 C4 C3 120.1(2)
C5 C4 H4 119.9
C3 C4 H4 119.9
C4 C5 C6 120.6(2)
C4 C5 H5 119.7
C6 C5 H5 119.7
C5 C6 C1 118.6(2)
C5 C6 C7 122.84(19)
C1 C6 C7 118.6(2)
N2 C7 C6 118.44(19)
N2 C7 C8 121.0(2)
C6 C7 C8 120.44(18)
O2 C8 N1 121.07(19)
O2 C8 C7 124.0(2)
N1 C8 C7 114.90(18)
C10 C9 N1 119.0(2)
C10 C9 C11 121.71(19)
N1 C9 C11 119.30(19)
C9 C10 N2 121.63(19)
C9 C10 H10 119.2
N2 C10 H10 119.2
O4 C11 O3 125.3(2)
O4 C11 C9 123.6(2)
O3 C11 C9 111.11(18)
O3 C12 H12A 109.5
O3 C12 H12B 109.5
H12A C12 H12B 109.5
O3 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.357(3)
O1 H1O 0.93(3)
O2 C8 1.238(2)
O1W H1W 0.86(4)
O1W H2W 0.90(3)
O3 C11 1.326(3)
O3 C12 1.447(3)
O4 C11 1.208(3)
N1 C8 1.364(3)
N1 C9 1.371(3)
N1 H1N 0.94(3)
N2 C7 1.322(3)
N2 C10 1.366(3)
C1 C2 1.378(3)
C1 C6 1.401(3)
C1 H1 0.9500
C2 C3 1.390(3)
C2 H2 0.9500
C3 C4 1.385(3)
C4 C5 1.380(3)
C4 H4 0.9500
C5 C6 1.398(3)
C5 H5 0.9500
C6 C7 1.466(3)
C7 C8 1.475(3)
C9 C10 1.352(3)
C9 C11 1.480(3)
C10 H10 0.9500
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
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
_geom_hbond_publ_flag
N1 H1N O2 2_566 0.94(3) 1.88(3) 2.805(2) 172(3) yes
O1 H1O O1W 1_555 0.93(3) 1.77(3) 2.682(3) 168(3) yes
O1W H1W O4 1_554 0.86(4) 2.02(4) 2.864(2) 167(3) yes
O1W H2W N2 2_675 0.90(3) 1.97(3) 2.838(3) 163(3) yes
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
C6 C1 C2 C3 -1.5(3)
C1 C2 C3 O1 -178.9(2)
C1 C2 C3 C4 0.8(3)
O1 C3 C4 C5 -179.5(2)
C2 C3 C4 C5 0.7(3)
C3 C4 C5 C6 -1.5(3)
C4 C5 C6 C1 0.8(3)
C4 C5 C6 C7 -177.9(2)
C2 C1 C6 C5 0.7(3)
C2 C1 C6 C7 179.5(2)
C10 N2 C7 C6 175.74(19)
C10 N2 C7 C8 -0.9(3)
C5 C6 C7 N2 143.9(2)
C1 C6 C7 N2 -34.8(3)
C5 C6 C7 C8 -39.4(3)
C1 C6 C7 C8 141.9(2)
C9 N1 C8 O2 179.85(19)
C9 N1 C8 C7 -2.0(3)
N2 C7 C8 O2 -179.8(2)
C6 C7 C8 O2 3.6(3)
N2 C7 C8 N1 2.1(3)
C6 C7 C8 N1 -174.48(19)
C8 N1 C9 C10 0.7(3)
C8 N1 C9 C11 -179.89(19)
N1 C9 C10 N2 0.7(3)
C11 C9 C10 N2 -178.7(2)
C7 N2 C10 C9 -0.5(3)
C12 O3 C11 O4 1.8(3)
C12 O3 C11 C9 -177.80(18)
C10 C9 C11 O4 -1.6(3)
N1 C9 C11 O4 179.0(2)
C10 C9 C11 O3 178.00(19)
N1 C9 C11 O3 -1.4(3)

_cod_database_fobs_code 1544581
