#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/51/4505173.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_4505173
loop_
_publ_author_name
'Rafilovich, Michal'
'Bernstein, Joel'
'Harris, Robin K.'
'Apperley, David C.'
'Karamertzanis, Panagiotis G.'
'Price, Sarah L.'
_publ_section_title
;
 Groth's Original Concomitant Polymorphs Revisited
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2197
_journal_paper_doi               10.1021/cg050151j
_journal_volume                  5
_journal_year                    2005
_chemical_formula_sum            'C13 H10 N4 O5'
_chemical_formula_weight         302.25
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.5000(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.6868(3)
_cell_length_b                   18.4268(12)
_cell_length_c                   14.7201(9)
_cell_measurement_temperature    373(2)
_cell_volume                     1271.22(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      373(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3689
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.125
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0732P)²+0.4435P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1212
_reflns_number_gt                3331
_reflns_number_total             3689
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg050151jsi20050414_050613.cif
_cod_data_source_block           mnpu_d
_cod_database_code               4505173
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O3 O 0.3061(2) 0.32415(5) 0.81933(7) 0.0281(2) Uani 1 1 d .
O2 O 0.1571(2) 0.42918(6) 0.86502(7) 0.0297(2) Uani 1 1 d .
O1 O 0.77007(16) 0.64534(4) 0.54582(6) 0.01593(18) Uani 1 1 d .
O4 O 1.04627(19) 0.77301(5) 0.30087(6) 0.02122(19) Uani 1 1 d .
O5 O 0.90482(19) 0.87869(5) 0.25531(6) 0.0220(2) Uani 1 1 d .
N1 N 0.3776(2) 0.59696(5) 0.61554(7) 0.01481(19) Uani 1 1 d .
H01 H 0.211(4) 0.6083(10) 0.6370(12) 0.029(4) Uiso 1 1 d .
N2 N 0.2906(2) 0.39033(6) 0.81240(7) 0.0198(2) Uani 1 1 d .
N3 N 0.3440(2) 0.70635(5) 0.54510(7) 0.01450(19) Uani 1 1 d .
H03 H 0.168(4) 0.7033(11) 0.5594(13) 0.035(5) Uiso 1 1 d .
N4 N 0.8936(2) 0.82650(5) 0.30746(6) 0.01472(19) Uani 1 1 d .
C2 C 0.4857(2) 0.52914(6) 0.64099(7) 0.0129(2) Uani 1 1 d .
C3 C 0.3542(2) 0.49464(6) 0.71402(7) 0.0141(2) Uani 1 1 d .
C4 C 0.4389(2) 0.42540(6) 0.73678(7) 0.0154(2) Uani 1 1 d .
C5 C 0.6511(3) 0.38775(6) 0.69192(8) 0.0179(2) Uani 1 1 d .
C6 C 0.7830(2) 0.42334(6) 0.62051(8) 0.0174(2) Uani 1 1 d .
C7 C 0.7022(2) 0.49307(6) 0.59455(7) 0.0151(2) Uani 1 1 d .
H7 H 0.7926 0.5157 0.5462 0.018 Uiso 1 1 calc R
C1 C 0.5173(2) 0.64931(6) 0.56684(7) 0.0128(2) Uani 1 1 d .
C8 C 0.4247(2) 0.76804(6) 0.49572(7) 0.0126(2) Uani 1 1 d .
C9 C 0.6304(2) 0.76583(6) 0.42796(7) 0.0129(2) Uani 1 1 d .
H9 H 0.7280 0.7232 0.4149 0.016 Uiso 1 1 calc R
C10 C 0.6842(2) 0.82942(6) 0.38082(7) 0.0132(2) Uani 1 1 d .
C11 C 0.5486(2) 0.89473(6) 0.39793(8) 0.0164(2) Uani 1 1 d .
H11 H 0.5930 0.9365 0.3654 0.020 Uiso 1 1 calc R
C12 C 0.3439(2) 0.89548(6) 0.46543(8) 0.0175(2) Uani 1 1 d .
H12 H 0.2478 0.9384 0.4785 0.021 Uiso 1 1 calc R
C13 C 0.2810(2) 0.83294(6) 0.51369(8) 0.0155(2) Uani 1 1 d .
H13 H 0.1421 0.8342 0.5584 0.019 Uiso 1 1 calc R
H3 H 0.208(4) 0.5183(9) 0.7484(11) 0.021(4) Uiso 1 1 d .
H6 H 0.927(4) 0.3989(9) 0.5889(11) 0.024(4) Uiso 1 1 d .
H5 H 0.705(4) 0.3407(10) 0.7118(12) 0.026(4) Uiso 1 1 d .
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
C1 N1 C2 126.52(9)
O3 N2 O2 123.83(11)
O3 N2 C4 118.24(11)
O2 N2 C4 117.93(10)
C1 N3 C8 125.65(9)
O4 N4 O5 123.48(10)
O4 N4 C10 118.95(9)
O5 N4 C10 117.57(9)
C3 C2 C7 119.17(10)
C3 C2 N1 116.86(9)
C7 C2 N1 123.86(10)
C4 C3 C2 118.74(10)
C3 C4 C5 123.71(10)
C3 C4 N2 117.07(10)
C5 C4 N2 119.21(10)
C4 C5 C6 116.78(10)
C5 C6 C7 121.47(11)
C6 C7 C2 120.12(10)
O1 C1 N3 124.04(10)
O1 C1 N1 123.74(10)
N3 C1 N1 112.22(9)
C9 C8 C13 119.83(10)
C9 C8 N3 122.56(10)
C13 C8 N3 117.55(10)
C10 C9 C8 117.62(10)
C11 C10 C9 123.89(10)
C11 C10 N4 118.49(10)
C9 C10 N4 117.61(9)
C10 C11 C12 117.40(10)
C13 C12 C11 120.66(10)
C12 C13 C8 120.59(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 N2 1.2258(14)
O2 N2 1.2299(15)
O1 C1 1.2290(13)
O4 N4 1.2225(13)
O5 N4 1.2319(13)
N1 C1 1.3716(13)
N1 C2 1.3984(14)
N2 C4 1.4675(14)
N3 C1 1.3648(14)
N3 C8 1.4031(13)
N4 C10 1.4663(14)
C2 C3 1.3968(14)
C2 C7 1.3969(14)
C3 C4 1.3767(15)
C4 C5 1.3848(16)
C5 C6 1.3886(17)
C6 C7 1.3919(16)
C8 C9 1.3938(14)
C8 C13 1.3987(15)
C9 C10 1.3862(14)
C10 C11 1.3851(15)
C11 C12 1.3873(16)
C12 C13 1.3867(16)
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
C1 N1 C2 C3 158.99(11)
C1 N1 C2 C7 -24.98(17)
C7 C2 C3 C4 -1.26(16)
N1 C2 C3 C4 174.97(10)
C2 C3 C4 C5 0.80(17)
C2 C3 C4 N2 -178.48(10)
O3 N2 C4 C3 161.43(11)
O2 N2 C4 C3 -18.35(15)
O3 N2 C4 C5 -17.89(16)
O2 N2 C4 C5 162.33(11)
C3 C4 C5 C6 0.30(17)
N2 C4 C5 C6 179.56(10)
C4 C5 C6 C7 -0.94(17)
C5 C6 C7 C2 0.49(17)
C3 C2 C7 C6 0.64(16)
N1 C2 C7 C6 -175.30(10)
C8 N3 C1 O1 0.47(18)
C8 N3 C1 N1 -179.96(10)
C2 N1 C1 O1 -6.72(18)
C2 N1 C1 N3 173.72(10)
C1 N3 C8 C9 31.72(16)
C1 N3 C8 C13 -151.16(11)
C13 C8 C9 C10 0.15(15)
N3 C8 C9 C10 177.21(10)
C8 C9 C10 C11 0.83(16)
C8 C9 C10 N4 -177.96(9)
O4 N4 C10 C11 168.64(10)
O5 N4 C10 C11 -11.53(15)
O4 N4 C10 C9 -12.50(15)
O5 N4 C10 C9 167.33(10)
C9 C10 C11 C12 -1.10(17)
N4 C10 C11 C12 177.69(10)
C10 C11 C12 C13 0.37(17)
C11 C12 C13 C8 0.55(17)
C9 C8 C13 C12 -0.82(16)
N3 C8 C13 C12 -178.03(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 207665
