#------------------------------------------------------------------------------
#$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2101522.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_2101522
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_volume                  52
_journal_year                    1996
_chemical_formula_sum            'C11 H11 Cl2 N3 O3'
_chemical_formula_weight         304.13
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_type_scat_source           IntTabC
_cell_angle_alpha                107.407(5)
_cell_angle_beta                 99.304(6)
_cell_angle_gamma                95.032(4)
_cell_formula_units_Z            2
_cell_length_a                   6.1501(4)
_cell_length_b                   8.3787(4)
_cell_length_c                   13.7356(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      53.83
_cell_measurement_theta_min      32.68
_cell_volume                     659.50(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       \w-2\q
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2724
_diffrn_reflns_theta_max         74.76
_diffrn_standards_decay_%        <5
_diffrn_standards_interval_time  33.33
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.523
_exptl_absorpt_correction_T_max  0.49
_exptl_absorpt_correction_T_min  0.31
_exptl_absorpt_correction_type   'DIRDIF (Walker & Stuart, 1983)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_description       prism
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.315
_refine_ls_extinction_coef       0.0050(10)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_obs   1.078
_refine_ls_hydrogen_treatment
'methyl H atoms fixed, all parameters refined for other H atoms'
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2723
_refine_ls_R_factor_obs          0.0425
_refine_ls_shift/esd_max         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;w = 1/[\s^2^(F^2^) + (0.0728P)^2^ + 0.1510P]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_obs         0.1276
_reflns_number_observed          2599
_reflns_number_total             2724
_reflns_observed_criterion       I>2\s(I)
_[local]_cod_data_source_file    cr0473.cif
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
N(1) -.0382(3) .8427(2) -.27610(10) .0430(10)
C(2) .1638(3) .9373(2) -.25040(10) .0440(10)
O(2) .2407(3) 1.0002(2) -.30850(10) .0630(10)
C(3) .2982(3) .9629(2) -.14140(10) .0410(10)
O(3) .4809(2) 1.0469(2) -.11260(10) .0550(10)
N(4) .2002(3) .8875(2) -.08120(10) .0390(10)
C(4A) -.0106(3) .7937(2) -.11220(10) .0360(10)
C(5) -.1060(3) .7195(2) -.04750(10) .0420(10)
Cl(5) .04500(10) .74360(10) .07460(10) .0550(10)
C(6) -.3159(3) .6266(2) -.0797(2) .0470(10)
C(7) -.4317(3) .6063(2) -.1783(2) .0450(10)
Cl(7) -.69440(10) .48620(10) -.22010(10) .0670(10)
C(8) -.3454(3) .6764(2) -.24530(10) .0430(10)
C(8A) -.1339(3) .7709(2) -.21110(10) .0380(10)
O(1S) -.3438(3) .7529(2) -.46220(10) .0680(10)
C(1S) -.4352(4) .7870(3) -.5381(2) .0510(10)
N(1S) -.6492(3) .7458(2) -.57940(10) .0480(10)
C(11S) -.7440(5) .7869(3) -.6714(2) .0690(10)
C(12S) -.7976(4) .6555(4) -.5353(2) .0680(10)
H(1) -.115(4) .825(3) -.333(2) .056(7)
H(4) .288(4) .907(3) -.0212(19) .047(6)
H(6) -.380(4) .580(3) -.035(2) .065(7)
H(8) -.435(4) .665(3) -.3129(19) .049(6)
H(1S) -.335(5) .851(4) -.572(2) .078(8)
H(11A) -.857(2) .857(2) -.6557(5) .090
H(11B) -.809(3) .6847(4) -.7267(5) .090
H(11C) -.6290(7) .846(2) -.6927(9) .090
H(12A) -.899(2) .5694(16) -.5903(2) .088
H(12B) -.881(2) .7331(6) -.4952(13) .088
H(12C) -.7120(5) .604(2) -.4911(12) .088
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N(1) C(2) 1.347(2)
N(1) C(8A) 1.391(2)
N(1) H(1) .81(3)
C(2) O(2) 1.213(2)
C(2) C(3) 1.531(2)
C(3) O(3) 1.211(2)
C(3) N(4) 1.361(2)
N(4) C(4A) 1.386(2)
N(4) H(4) .87(3)
C(4A) C(8A) 1.394(2)
C(4A) C(5) 1.398(2)
C(5) C(6) 1.379(3)
C(5) Cl(5) 1.726(2)
C(6) C(7) 1.378(3)
C(6) H(6) .94(3)
C(7) C(8) 1.379(3)
C(7) Cl(7) 1.738(2)
C(8) C(8A) 1.392(3)
C(8) H(8) .97(2)
O(1S) C(1S) 1.225(3)
C(1S) N(1S) 1.317(3)
C(1S) H(1S) 1.03(3)
N(1S) C(12S) 1.451(3)
N(1S) C(11S) 1.454(2)
C(11S) H(11A) .96
C(11S) H(11B) .96
C(11S) H(11C) .96
C(12S) H(12A) .96
C(12S) H(12B) .96
C(12S) H(12C) .96
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) 125.2(2)
C(2) N(1) H(1) 120(2)
C(8A) N(1) H(1) 114(2)
O(2) C(2) N(1) 123.5(2)
O(2) C(2) C(3) 120.1(2)
N(1) C(2) C(3) 116.4(2)
O(3) C(3) N(4) 123.4(2)
O(3) C(3) C(2) 120.3(2)
N(4) C(3) C(2) 116.4(2)
C(3) N(4) C(4A) 124.1(2)
C(3) N(4) H(4) 110(2)
C(4A) N(4) H(4) 125(2)
N(4) C(4A) C(8A) 119.7(2)
N(4) C(4A) C(5) 122.3(2)
C(8A) C(4A) C(5) 118.0(2)
C(6) C(5) C(4A) 121.5(2)
C(6) C(5) Cl(5) 119.68(14)
C(4A) C(5) Cl(5) 118.9(2)
C(7) C(6) C(5) 118.7(2)
C(7) C(6) H(6) 121(2)
C(5) C(6) H(6) 120(2)
C(6) C(7) C(8) 122.3(2)
C(6) C(7) Cl(7) 118.8(2)
C(8) C(7) Cl(7) 118.9(2)
C(7) C(8) C(8A) 118.2(2)
C(7) C(8) H(8) 119.9(14)
C(8A) C(8) H(8) 121.8(14)
N(1) C(8A) C(8) 120.5(2)
N(1) C(8A) C(4A) 118.1(2)
C(8) C(8A) C(4A) 121.4(2)
O(1S) C(1S) N(1S) 124.5(2)
O(1S) C(1S) H(1S) 117(2)
N(1S) C(1S) H(1S) 119(2)
C(1S) N(1S) C(12S) 121.0(2)
C(1S) N(1S) C(11S) 121.2(2)
C(12S) N(1S) C(11S) 117.8(2)
N(1S) C(11S) H(11A) 109.47(14)
N(1S) C(11S) H(11B) 109.47(12)
H(11A) C(11S) H(11B) 109.5
N(1S) C(11S) H(11C) 109.47(13)
H(11A) C(11S) H(11C) 109.5
H(11B) C(11S) H(11C) 109.5
N(1S) C(12S) H(12A) 109.47(12)
N(1S) C(12S) H(12B) 109.47(13)
H(12A) C(12S) H(12B) 109.5
N(1S) C(12S) H(12C) 109.47(13)
H(12A) C(12S) H(12C) 109.5
H(12B) C(12S) H(12C) 109.5
_cod_database_code 2101522