#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:26:29 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180262 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/48/7114804.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_7114804
loop_
_publ_author_name
'Adams, Harry'
'Bernad Jr., Pablo L.'
'Hembury, Guy A.'
'Hunter, Christopher A.'
'McCabe, James F.'
'Eggleston, Drake S.'
'Haltiwanger, R. Curtis'
'Livingstone, David J.'
'D. M. Harris, Kenneth'
'Kariuki, Benson M.'
_publ_section_title
;
 Substituent effects on aromatic interactions in the solid state
;
_journal_issue                   16
_journal_name_full               'Chemical Communications'
_journal_page_first              1500
_journal_paper_doi               10.1039/b101575n
_journal_year                    2001
_chemical_formula_sum            'C13 H10 N2 O3'
_chemical_formula_weight         242.23
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.61(4)
_cell_angle_beta                 98.64(5)
_cell_angle_gamma                92.87(3)
_cell_formula_units_Z            2
_cell_length_a                   5.218(2)
_cell_length_b                   8.412(3)
_cell_length_c                   13.249(6)
_cell_measurement_temperature    293(2)
_cell_volume                     559.0(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.822
_diffrn_measured_fraction_theta_max 0.822
_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  0.0917
_diffrn_reflns_av_sigmaI/netI    0.0627
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2075
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.07(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1611
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0664
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1253P)²+0.1381P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1922
_refine_ls_wR_factor_ref         0.2196
_reflns_number_gt                1226
_reflns_number_total             1611
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b101575n.txt
_cod_data_source_block           gah06
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7114804
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O 0.3829(4) 0.2201(3) 0.49448(17) 0.0545(7) Uani 1 1 d .
O2 O 0.4490(6) -0.2762(4) 0.0116(2) 0.0836(9) Uani 1 1 d .
O3 O 0.7624(6) -0.1149(4) -0.0032(2) 0.0812(9) Uani 1 1 d .
N1 N 0.8206(5) 0.2786(3) 0.52374(19) 0.0451(7) Uani 1 1 d .
H1A H 0.9586 0.2661 0.4956 0.054 Uiso 1 1 calc R
N2 N 0.6058(6) -0.1583(4) 0.0462(2) 0.0552(8) Uani 1 1 d .
C1 C 0.8532(6) 0.3699(4) 0.6295(2) 0.0400(7) Uani 1 1 d .
C2 C 1.0703(6) 0.3503(4) 0.6981(2) 0.0458(8) Uani 1 1 d .
H2A H 1.1896 0.2782 0.6749 0.055 Uiso 1 1 calc R
C3 C 1.1099(6) 0.4371(4) 0.8005(3) 0.0514(9) Uani 1 1 d .
H3A H 1.2572 0.4242 0.8461 0.062 Uiso 1 1 calc R
C4 C 0.9314(6) 0.5444(4) 0.8369(3) 0.0500(9) Uani 1 1 d .
H4A H 0.9557 0.6010 0.9067 0.060 Uiso 1 1 calc R
C5 C 0.7189(7) 0.5649(4) 0.7674(3) 0.0514(9) Uani 1 1 d .
H5A H 0.6009 0.6381 0.7906 0.062 Uiso 1 1 calc R
C6 C 0.6765(6) 0.4795(4) 0.6641(2) 0.0463(8) Uani 1 1 d .
H6A H 0.5317 0.4949 0.6181 0.056 Uiso 1 1 calc R
C7 C 0.5929(6) 0.2095(4) 0.4633(2) 0.0411(8) Uani 1 1 d .
C8 C 0.6064(5) 0.1148(3) 0.3542(2) 0.0387(7) Uani 1 1 d .
C9 C 0.7935(6) 0.1536(4) 0.2963(2) 0.0466(8) Uani 1 1 d .
H9A H 0.9193 0.2400 0.3262 0.056 Uiso 1 1 calc R
C10 C 0.7946(6) 0.0662(4) 0.1960(2) 0.0479(9) Uani 1 1 d .
H10A H 0.9189 0.0925 0.1574 0.057 Uiso 1 1 calc R
C11 C 0.6058(6) -0.0620(4) 0.1538(2) 0.0429(8) Uani 1 1 d .
C12 C 0.4175(6) -0.1047(4) 0.2085(3) 0.0480(8) Uani 1 1 d .
H12A H 0.2936 -0.1923 0.1787 0.058 Uiso 1 1 calc R
C13 C 0.4190(6) -0.0135(4) 0.3085(2) 0.0460(8) Uani 1 1 d .
H13A H 0.2917 -0.0386 0.3460 0.055 Uiso 1 1 calc R
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
C7 N1 C1 126.1(2)
O3 N2 O2 123.3(3)
O3 N2 C11 118.2(3)
O2 N2 C11 118.6(3)
C2 C1 C6 119.9(3)
C2 C1 N1 118.3(2)
C6 C1 N1 121.8(3)
C3 C2 C1 120.1(3)
C2 C3 C4 120.7(3)
C5 C4 C3 118.6(3)
C4 C5 C6 121.5(3)
C5 C6 C1 119.1(3)
O1 C7 N1 122.9(3)
O1 C7 C8 120.3(3)
N1 C7 C8 116.8(2)
C13 C8 C9 118.9(3)
C13 C8 C7 118.1(3)
C9 C8 C7 123.0(3)
C10 C9 C8 121.0(3)
C9 C10 C11 118.1(3)
C10 C11 C12 122.6(3)
C10 C11 N2 118.8(3)
C12 C11 N2 118.6(3)
C13 C12 C11 117.9(3)
C12 C13 C8 121.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.228(4)
O2 N2 1.213(4)
O3 N2 1.210(4)
N1 C7 1.354(4)
N1 C1 1.424(4)
N2 C11 1.478(4)
C1 C2 1.382(4)
C1 C6 1.392(4)
C2 C3 1.373(4)
C3 C4 1.394(4)
C4 C5 1.374(5)
C5 C6 1.379(5)
C7 C8 1.504(4)
C8 C13 1.385(4)
C8 C9 1.397(4)
C9 C10 1.373(4)
C10 C11 1.382(5)
C11 C12 1.383(4)
C12 C13 1.377(4)
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
C7 N1 C1 C2 141.9(3)
C7 N1 C1 C6 -39.6(4)
C6 C1 C2 C3 0.9(4)
N1 C1 C2 C3 179.5(3)
C1 C2 C3 C4 0.7(5)
C2 C3 C4 C5 -1.8(5)
C3 C4 C5 C6 1.4(5)
C4 C5 C6 C1 0.0(5)
C2 C1 C6 C5 -1.2(4)
N1 C1 C6 C5 -179.8(3)
C1 N1 C7 O1 0.6(5)
C1 N1 C7 C8 -178.5(2)
O1 C7 C8 C13 -28.1(4)
N1 C7 C8 C13 151.0(3)
O1 C7 C8 C9 149.8(3)
N1 C7 C8 C9 -31.0(4)
C13 C8 C9 C10 -0.4(4)
C7 C8 C9 C10 -178.4(3)
C8 C9 C10 C11 -0.3(4)
C9 C10 C11 C12 0.1(4)
C9 C10 C11 N2 -179.4(3)
O3 N2 C11 C10 -4.3(4)
O2 N2 C11 C10 175.9(3)
O3 N2 C11 C12 176.1(3)
O2 N2 C11 C12 -3.6(4)
C10 C11 C12 C13 0.7(4)
N2 C11 C12 C13 -179.7(2)
C11 C12 C13 C8 -1.4(4)
C9 C8 C13 C12 1.3(4)
C7 C8 C13 C12 179.4(2)
