#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:17:07 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178378 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/00/4020016.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4020016
loop_
_publ_author_name
'Francesca Aulenta'
'Michael G.B. Drew'
'Alison Foster'
'Wayne Hayes'
'Steven Rannard'
'David W. Thornthwaite'
'David R. Worrall'
'Tristan G.A. Youngs'
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              63
_journal_page_last               78
_journal_paper_doi               10.1021/jo048799a
_journal_volume                  70
_journal_year                    2005
_chemical_formula_sum            'C12 H10 N2 O6'
_chemical_formula_weight         278.22
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 102.443(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.511(14)
_cell_length_b                   5.682(8)
_cell_length_c                   18.53(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1286(3)
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Marresearch Image Plate'
_diffrn_measurement_method
'95 frames at 2^o intervals, counting time 2 min.'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7049
_diffrn_reflns_theta_max         25.84
_diffrn_reflns_theta_min         2.25
_diffrn_standards_decay_%        ?
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelopiped
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_ls_extinction_coef       0.0097(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.264
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2430
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.264
_refine_ls_R_factor_all          0.1252
_refine_ls_R_factor_gt           0.0953
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0405P)²+1.8846P] where P=(Fo²+2Fc²)/3'
_refine_ls_wR_factor_gt          0.1773
_refine_ls_wR_factor_ref         0.1895
_reflns_number_gt                1842
_reflns_number_total             2430
_reflns_threshold_expression     >2sigma(I)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4020016
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5748(3) 0.5586(6) 0.59381(19) 0.0319(8) Uani 1 d . . .
N101 N 0.4701(3) 0.6814(6) 0.59396(18) 0.0421(8) Uani 1 d . . .
O102 O 0.4063(3) 0.5885(6) 0.6262(2) 0.0690(10) Uani 1 d . . .
O103 O 0.4528(3) 0.8677(6) 0.56106(19) 0.0650(10) Uani 1 d . . .
C2 C 0.5995(3) 0.3580(6) 0.63667(19) 0.0333(9) Uani 1 d . . .
H2 H 0.5518 0.2976 0.6642 0.040 Uiso 1 calc R . .
C3 C 0.6987(3) 0.2531(6) 0.63620(19) 0.0332(8) Uani 1 d . . .
N31 N 0.7294(3) 0.0414(6) 0.68275(17) 0.0409(8) Uani 1 d . . .
O32 O 0.8212(3) -0.0378(6) 0.68764(18) 0.0643(10) Uani 1 d . . .
O33 O 0.6614(3) -0.0435(5) 0.71314(16) 0.0549(8) Uani 1 d . . .
C4 C 0.7695(3) 0.3379(6) 0.59439(19) 0.0342(9) Uani 1 d . . .
H4 H 0.8355 0.2613 0.5954 0.041 Uiso 1 calc R . .
C5 C 0.7422(3) 0.5382(6) 0.55068(19) 0.0327(8) Uani 1 d . . .
C6 C 0.6424(3) 0.6493(7) 0.55091(19) 0.0346(9) Uani 1 d . . .
H6 H 0.6219 0.7832 0.5224 0.041 Uiso 1 calc R . .
C7 C 0.8194(3) 0.6278(7) 0.5076(2) 0.0411(10) Uani 1 d . . .
H7 H 0.8836 0.5421 0.5106 0.049 Uiso 1 calc R . .
C8 C 0.8078(3) 0.8158(7) 0.4651(2) 0.0453(10) Uani 1 d . . .
H8 H 0.7444 0.9056 0.4598 0.054 Uiso 1 calc R . .
C9 C 0.8930(3) 0.8869(8) 0.4257(2) 0.0470(11) Uani 1 d . . .
O9 O 0.9809(2) 0.7936(6) 0.43203(18) 0.0635(10) Uani 1 d . . .
O10 O 0.8603(2) 1.0678(6) 0.3812(2) 0.0745(12) Uani 1 d . . .
C11 C 0.9353(4) 1.1515(12) 0.3367(4) 0.098(2) Uani 1 d . . .
H11A H 0.9941 1.2396 0.3678 0.117 Uiso 1 calc R . .
H11B H 0.9673 1.0177 0.3167 0.117 Uiso 1 calc R . .
C12 C 0.8822(6) 1.2940(15) 0.2791(4) 0.120(3) Uani 1 d . . .
H12 H 0.8135 1.2343 0.2575 0.144 Uiso 1 calc R . .
C13 C 0.8998(7) 1.4648(15) 0.2510(5) 0.138(3) Uani 1 d . . .
H13A H 0.9659 1.5428 0.2674 0.165 Uiso 1 calc R . .
H13B H 0.8479 1.5255 0.2117 0.165 Uiso 1 calc R . .
