#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/15/2101518.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_2101518
loop_
_publ_author_name
'Kubicki, M.'
'Kindopp, T. W.'
'Capparelli, M. V.'
'Codding, P. W.'
_publ_section_title
;
 Hydrogen-bond patterns in 1,4-dihydro-2,3-quinoxalinediones: ligands
 for the glycine modulatory site on the NMDA receptor
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              487
_journal_page_last               499
_journal_paper_doi               10.1107/S0108768195011773
_journal_volume                  52
_journal_year                    1996
_chemical_formula_sum            'C8 H4 N4 O6'
_chemical_formula_weight         252.15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_type_scat_source           IntTabC
_cell_angle_alpha                90
_cell_angle_beta                 90.341(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4668(3)
_cell_length_b                   8.5533(4)
_cell_length_c                   12.4657(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      43.61
_cell_measurement_theta_min      19.58
_cell_volume                     902.74(7)
_computing_cell_refinement       'SHELXL03 (Sheldrick, 1993)'
_computing_data_collection       'Enraf-Nonius CAD-4F'
_computing_data_reduction        'ENDROC (Rettig, 1978)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_measurement_device       'Enraf-Nonius CAD-4F'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3846
_diffrn_reflns_theta_max         74.87
_diffrn_standards_decay_%        <3
_diffrn_standards_interval_time  33.33
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.439
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.855
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.172
_refine_ls_extinction_coef       0.0070(10)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_obs   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     180
_refine_ls_number_reflns         1851
_refine_ls_R_factor_obs          0.0314
_refine_ls_shift/esd_max         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;w = 1/[\s^2^(F^2^) + (0.0296P)^2^ + 0.2334P]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_obs         0.0874
_reflns_number_observed          1730
_reflns_number_total             1854
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            cr0473.cif
_cod_data_source_block           cr0473a
_cod_database_code               2101518
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
N(1) .77430(10) .26070(10) .46510(10) .0310(10)
C(2) .7091(2) .32010(10) .37370(10) .0290(10)
O(2) .72550(10) .45460(10) .34550(10) .0410(10)
C(3) .6107(2) .20740(10) .30650(10) .0300(10)
O(3) .54460(10) .25490(10) .22630(10) .0430(10)
N(4) .60020(10) .05740(10) .34130(10) .0280(10)
C(4A) .67750(10) .00110(10) .43220(10) .0240(10)
C(5) .66930(10) -.15660(10) .45980(10) .0250(10)
C(6) .74980(10) -.20700(10) .54950(10) .0240(10)
N(6) .75180(10) -.37610(10) .56870(10) .0280(10)
O(61) .88080(10) -.44010(10) .56850(10) .0380(10)
O(62) .62600(10) -.44210(10) .57910(10) .0450(10)
C(7) .83720(10) -.10470(10) .61280(10) .0250(10)
N(7) .91870(10) -.16050(10) .70930(10) .0280(10)
O(71) 1.04550(10) -.10110(10) .73210(10) .0430(10)
O(72) .85540(10) -.26440(10) .76080(10) .0400(10)
C(8) .8458(2) .05180(10) .58650(10) .0270(10)
C(8A) .76560(10) .10470(10) .49560(10) .0250(10)
H(1) .829(2) .328(2) .5045(14) .044(5)
H(4) .545(2) -.006(2) .3036(4) .044(4)
H(5) .612(2) -.2279(18) .4153(13) .037(4)
H(8) .9042(19) .1220(18) .6282(12) .034(4)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(2) N(1) C(8A) 124.44(11)
C(2) N(1) H(1) 115.3(11)
C(8A) N(1) H(1) 120.2(11)
O(2) C(2) N(1) 123.43(12)
O(2) C(2) C(3) 120.36(12)
N(1) C(2) C(3) 116.20(10)
O(3) C(3) N(4) 123.30(12)
O(3) C(3) C(2) 119.32(11)
N(4) C(3) C(2) 117.37(10)
C(3) N(4) C(4A) 123.79(11)
C(3) N(4) H(4) 117.4(12)
C(4A) N(4) H(4) 118.8(12)
N(4) C(4A) C(5) 120.82(11)
N(4) C(4A) C(8A) 119.12(10)
C(5) C(4A) C(8A) 120.06(11)
C(6) C(5) C(4A) 118.61(11)
C(6) C(5) H(5) 121.3(9)
C(4A) C(5) H(5) 120.1(10)
C(5) C(6) C(7) 121.61(11)
C(5) C(6) N(6) 116.55(10)
C(7) C(6) N(6) 121.56(10)
O(62) N(6) O(61) 125.25(11)
O(62) N(6) C(6) 117.89(11)
O(61) N(6) C(6) 116.79(10)
C(8) C(7) C(6) 120.34(11)
C(8) C(7) N(7) 119.09(11)
C(6) C(7) N(7) 120.56(10)
O(71) N(7) O(72) 124.71(11)
O(71) N(7) C(7) 117.71(10)
O(72) N(7) C(7) 117.58(11)
C(7) C(8) C(8A) 118.80(11)
C(7) C(8) H(8) 121.3(9)
C(8A) C(8) H(8) 119.9(9)
N(1) C(8A) C(8) 120.53(11)
N(1) C(8A) C(4A) 118.88(11)
C(8) C(8A) C(4A) 120.58(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N(1) C(2) 1.362(2)
N(1) C(8A) 1.3887(14)
N(1) H(1) .89(2)
C(2) O(2) 1.211(2)
C(2) C(3) 1.522(2)
C(3) O(3) 1.213(2)
C(3) N(4) 1.357(2)
N(4) C(4A) 1.3919(14)
N(4) H(4) .85(2)
C(4A) C(5) 1.394(2)
C(4A) C(8A) 1.399(2)
C(5) C(6) 1.375(2)
C(5) H(5) .95(2)
C(6) C(7) 1.389(2)
C(6) N(6) 1.4662(14)
N(6) O(62) 1.213(2)
N(6) O(61) 1.222(2)
C(7) C(8) 1.380(2)
C(7) N(7) 1.464(2)
N(7) O(71) 1.219(2)
N(7) O(72) 1.2221(14)
C(8) C(8A) 1.394(2)
C(8) H(8) .93(2)
