#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/30/1513070.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_1513070
loop_
_publ_author_name
'Ivanova, Bojidarka'
'Spiteller, Michael'
_publ_section_title
;
 Organic mandelates as promising materials with non-linear optical
 application
;
_journal_name_full               'Structural Chemistry'
_journal_page_first              989
_journal_paper_doi               10.1007/s11224-010-9635-5
_journal_volume                  21
_journal_year                    2010
_chemical_formula_moiety         'C9 H9 N2 O, C8 H7 O3'
_chemical_formula_sum            'C17 H16 N2 O4'
_chemical_formula_weight         312.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 99.73(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.332(4)
_cell_length_b                   25.455(19)
_cell_length_c                   11.078(7)
_cell_measurement_temperature    198(2)
_cell_volume                     1481.9(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker GIS'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker APEX2'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      198(2)
_diffrn_measured_fraction_theta_full 0.938
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2184
_diffrn_reflns_av_sigmaI/netI    0.4699
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4792
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9719
_exptl_absorpt_correction_T_min  0.9612
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorleass
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.762
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2562
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.762
_refine_ls_R_factor_all          0.3254
_refine_ls_R_factor_gt           0.0978
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0905P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2020
_refine_ls_wR_factor_ref         0.2865
_reflns_number_gt                535
_reflns_number_total             2562
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            Struct-100a.cif
_cod_data_source_block           bi100a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1482.0(19)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1513070
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
O4 O 0.3216(14) 0.2793(3) 0.5912(7) 0.060(2) Uani 1 1 d .
H1 H 0.4767 0.2774 0.6214 0.089 Uiso 1 1 calc R
N2 N 0.9054(14) 0.3147(3) -0.0462(6) 0.034(2) Uani 1 1 d .
H2 H 0.7981 0.2895 -0.0363 0.041 Uiso 1 1 calc R
O3 O 0.6335(13) 0.3172(2) 0.1374(7) 0.050(2) Uani 1 1 d .
H3 H 0.4802 0.3236 0.1091 0.074 Uiso 1 1 calc R
O2 O 0.6081(14) 0.2735(3) 0.4147(6) 0.057(2) Uani 1 1 d .
O1 O 0.3731(15) 0.3325(3) 0.2986(6) 0.056(3) Uani 1 1 d .
N1 N 0.9968(15) 0.2688(3) -0.2121(6) 0.050(3) Uani 1 1 d .
H4 H 0.8789 0.2459 -0.2016 0.060 Uiso 1 1 calc R
H5 H 1.0840 0.2646 -0.2721 0.060 Uiso 1 1 calc R
C17 C 0.9245(19) 0.3574(3) 0.0316(8) 0.027(3) Uani 1 1 d .
C16 C 1.0909(19) 0.3984(4) 0.0146(9) 0.041(3) Uani 1 1 d .
C15 C 1.225(2) 0.3485(4) -0.1512(9) 0.050(3) Uani 1 1 d .
H6 H 1.3300 0.3448 -0.2118 0.059 Uiso 1 1 calc R
C14 C 0.7755(19) 0.3596(4) 0.1227(9) 0.040(3) Uani 1 1 d .
C13 C 0.784(2) 0.4029(4) 0.1962(9) 0.049(3) Uani 1 1 d .
H7 H 0.6804 0.4048 0.2578 0.059 Uiso 1 1 calc R
C6 C 0.371(2) 0.3723(4) 0.5529(9) 0.029(3) Uani 1 1 d .
C5 C 0.605(2) 0.3793(4) 0.6270(9) 0.044(3) Uani 1 1 d .
H8 H 0.7193 0.3505 0.6414 0.052 Uiso 1 1 calc R
C12 C 1.102(2) 0.4421(4) 0.0950(9) 0.051(3) Uani 1 1 d .
H9 H 1.2191 0.4698 0.0890 0.061 Uiso 1 1 calc R
C11 C 1.044(2) 0.3101(4) -0.1366(9) 0.039(3) Uani 1 1 d .
C7 C 0.286(2) 0.3187(4) 0.4991(8) 0.047(3) Uani 1 1 d .
H10 H 0.1007 0.3205 0.4631 0.056 Uiso 1 1 calc R
C4 C 0.289(3) 0.4628(4) 0.5845(10) 0.063(4) Uani 1 1 d .
H11 H 0.1814 0.4926 0.5670 0.075 Uiso 1 1 calc R
C10 C 0.949(2) 0.4446(4) 0.1795(10) 0.070(4) Uani 1 1 d .
H12 H 0.9511 0.4752 0.2290 0.084 Uiso 1 1 calc R
C8 C 0.441(2) 0.3074(4) 0.3946(9) 0.039(3) Uani 1 1 d .
C9 C 1.246(2) 0.3910(4) -0.0770(9) 0.055(4) Uani 1 1 d .
H13 H 1.3698 0.4169 -0.0862 0.066 Uiso 1 1 calc R
C3 C 0.517(3) 0.4676(5) 0.6597(11) 0.061(4) Uani 1 1 d .
H14 H 0.5652 0.5003 0.6984 0.074 Uiso 1 1 calc R
C2 C 0.674(3) 0.4260(5) 0.6790(11) 0.064(4) Uani 1 1 d .
H15 H 0.8354 0.4297 0.7299 0.077 Uiso 1 1 calc R
C1 C 0.212(2) 0.4147(4) 0.5333(9) 0.048(3) Uani 1 1 d .
H16 H 0.0486 0.4110 0.4845 0.057 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
C11 N2 C17 122.9(8)
N2 C17 C14 119.7(8)
N2 C17 C16 118.9(8)
C14 C17 C16 121.3(9)
C17 C16 C12 117.4(9)
C17 C16 C9 117.0(9)
C12 C16 C9 125.5(10)
C9 C15 C11 118.5(9)
O3 C14 C13 122.5(8)
O3 C14 C17 117.4(9)
C13 C14 C17 120.1(9)
C14 C13 C10 119.3(9)
C1 C6 C5 117.7(10)
C1 C6 C7 120.6(11)
C5 C6 C7 121.7(10)
C2 C5 C6 121.5(11)
C10 C12 C16 120.5(10)
N1 C11 N2 117.8(9)
N1 C11 C15 122.3(8)
N2 C11 C15 119.9(9)
O4 C7 C6 110.8(8)
O4 C7 C8 112.3(8)
C6 C7 C8 107.0(7)
C3 C4 C1 120.2(12)
C12 C10 C13 121.4(10)
O2 C8 O1 127.7(9)
O2 C8 C7 116.9(10)
O1 C8 C7 115.4(9)
C15 C9 C16 122.6(10)
C2 C3 C4 119.7(12)
C3 C2 C5 120.6(13)
C6 C1 C4 120.2(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C7 1.418(10)
N2 C11 1.345(10)
N2 C17 1.379(10)
O3 C14 1.344(10)
O2 C8 1.235(11)
O1 C8 1.240(11)
N1 C11 1.340(11)
C17 C14 1.387(11)
C17 C16 1.403(12)
C16 C12 1.420(12)
C16 C9 1.427(12)
C15 C9 1.350(12)
C15 C11 1.403(12)
C14 C13 1.366(12)
C13 C10 1.410(13)
C6 C1 1.365(12)
C6 C5 1.385(13)
C6 C7 1.528(12)
C5 C2 1.346(13)
C12 C10 1.346(12)
C7 C8 1.559(11)
C4 C3 1.359(14)
C4 C1 1.382(13)
C3 C2 1.345(14)
