#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/31/1513167.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_1513167
loop_
_publ_author_name
'Ivanova, Bojidarka'
'Spiteller, Michael'
_publ_section_title
;
 Noncentrosymmetric Crystals with Marked Nonlinear Optical Properties
;
_journal_name_full               'Journal of Physical Chemistry A'
_journal_page_first              5099
_journal_page_last               5103
_journal_paper_doi               10.1021/jp1002758
_journal_volume                  114
_journal_year                    2010
_chemical_absolute_configuration rmad
_chemical_formula_moiety         C6H16N2,2(C4HO4)
_chemical_formula_sum            'C14 H18 N2 O8'
_chemical_formula_weight         342.30
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5616(12)
_cell_length_b                   13.630(3)
_cell_length_c                   14.338(3)
_cell_measurement_temperature    300(2)
_cell_volume                     1477.7(5)
_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      300(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.1480
_diffrn_reflns_av_sigmaI/netI    0.1816
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14185
_diffrn_reflns_theta_full        25.15
_diffrn_reflns_theta_max         25.15
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.9720
_exptl_absorpt_correction_T_min  0.9519
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.7(19)
_refine_ls_extinction_coef       0.034(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2626
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.960
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0798
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.011
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0651P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1894
_refine_ls_wR_factor_ref         0.1987
_reflns_number_gt                2194
_reflns_number_total             1539
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            Struct-15a.cif
_cod_data_source_block           bi15
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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        1477.7(4)
_cod_database_code               1513167
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
O14 O -0.0106(4) 0.07952(18) 0.35994(16) 0.0358(7) Uani 1 1 d .
O10 O -0.1150(4) 0.44805(18) 0.23570(17) 0.0341(7) Uani 1 1 d .
H10 H -0.0625 0.4915 0.2074 0.051 Uiso 1 1 calc R
O11 O 0.1223(5) -0.09699(19) 0.49768(18) 0.0417(8) Uani 1 1 d .
O13 O -0.1339(5) 0.20189(19) 0.53915(18) 0.0440(9) Uani 1 1 d .
H13 H -0.1167 0.2372 0.4937 0.066 Uiso 1 1 calc R
O7 O -0.1675(4) 0.29698(18) 0.39511(17) 0.0353(7) Uani 1 1 d .
O8 O 0.0400(5) 0.4414(2) 0.54211(18) 0.0506(9) Uani 1 1 d .
N2 N -0.2373(4) 0.2798(2) 0.1448(2) 0.0326(8) Uani 1 1 d .
H2A H -0.2200 0.3101 0.0906 0.049 Uiso 1 1 calc R
H2B H -0.1677 0.2273 0.1482 0.049 Uiso 1 1 calc R
H2C H -0.2114 0.3206 0.1914 0.049 Uiso 1 1 calc R
O9 O 0.0909(5) 0.5969(2) 0.3750(2) 0.0486(9) Uani 1 1 d .
O12 O -0.0332(5) 0.0255(2) 0.67246(17) 0.0462(8) Uani 1 1 d .
C14 C -0.0070(5) 0.0636(3) 0.4479(2) 0.0274(9) Uani 1 1 d .
C10 C -0.0714(6) 0.4506(3) 0.3219(2) 0.0293(9) Uani 1 1 d .
C8 C -0.0050(6) 0.4446(2) 0.4608(2) 0.0305(9) Uani 1 1 d .
C13 C -0.0651(6) 0.1184(3) 0.5249(2) 0.0294(9) Uani 1 1 d .
C9 C 0.0197(5) 0.5179(3) 0.3831(2) 0.0292(9) Uani 1 1 d .
C12 C -0.0187(6) 0.0390(3) 0.5891(2) 0.0298(9) Uani 1 1 d .
C11 C 0.0509(5) -0.0178(3) 0.5074(2) 0.0283(8) Uani 1 1 d .
C5 C -0.4268(5) 0.2487(2) 0.1523(2) 0.0283(9) Uani 1 1 d .
H5 H -0.4453 0.1919 0.1115 0.034 Uiso 1 1 calc R
N1 N -0.3659(5) 0.1343(2) 0.2853(2) 0.0347(8) Uani 1 1 d .
H1A H -0.3745 0.0852 0.2447 0.052 Uiso 1 1 calc R
H1B H -0.4066 0.1148 0.3405 0.052 Uiso 1 1 calc R
H1C H -0.2532 0.1521 0.2908 0.052 Uiso 1 1 calc R
C7 C -0.0954(5) 0.3805(3) 0.3946(2) 0.0273(9) Uani 1 1 d .
C6 C -0.5466(6) 0.3312(3) 0.1199(3) 0.0459(12) Uani 1 1 d .
H6A H -0.5207 0.3897 0.1559 0.055 Uiso 1 1 calc R
H6B H -0.5215 0.3455 0.0550 0.055 Uiso 1 1 calc R
C4 C -0.4723(5) 0.2193(3) 0.2517(2) 0.0284(9) Uani 1 1 d .
H4 H -0.4498 0.2754 0.2927 0.034 Uiso 1 1 calc R
C2 C -0.7824(7) 0.2754(4) 0.2294(3) 0.0509(12) Uani 1 1 d .
H2D H -0.7652 0.3305 0.2713 0.061 Uiso 1 1 calc R
H2E H -0.9054 0.2556 0.2331 0.061 Uiso 1 1 calc R
C3 C -0.6665(6) 0.1920(3) 0.2588(3) 0.0386(10) Uani 1 1 d .
H3A H -0.6900 0.1355 0.2196 0.046 Uiso 1 1 calc R
H3B H -0.6939 0.1742 0.3227 0.046 Uiso 1 1 calc R
C1 C -0.7396(6) 0.3069(4) 0.1299(3) 0.0553(13) Uani 1 1 d .
H1D H -0.7701 0.2543 0.0872 0.066 Uiso 1 1 calc R
H1E H -0.8100 0.3639 0.1137 0.066 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
O14 C14 C13 132.7(4)
O14 C14 C11 135.1(3)
C13 C14 C11 92.2(3)
O10 C10 C7 131.0(3)
O10 C10 C9 136.6(3)
C7 C10 C9 92.4(3)
O8 C8 C7 137.2(3)
O8 C8 C9 134.2(4)
C7 C8 C9 88.5(3)
O13 C13 C14 137.1(4)
O13 C13 C12 131.4(3)
C14 C13 C12 91.5(3)
O9 C9 C10 136.1(4)
O9 C9 C8 135.7(4)
C10 C9 C8 88.2(3)
O12 C12 C13 135.2(4)
O12 C12 C11 136.2(4)
C13 C12 C11 88.6(3)
O11 C11 C14 137.5(3)
O11 C11 C12 134.8(4)
C14 C11 C12 87.7(3)
N2 C5 C6 109.9(3)
N2 C5 C4 111.0(3)
C6 C5 C4 110.3(3)
O7 C7 C10 131.5(4)
O7 C7 C8 137.6(3)
C10 C7 C8 90.9(3)
C1 C6 C5 112.8(4)
N1 C4 C3 108.0(3)
N1 C4 C5 112.8(3)
C3 C4 C5 110.3(3)
C3 C2 C1 110.7(4)
C2 C3 C4 111.2(4)
C6 C1 C2 110.9(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O14 C14 1.281(4)
O10 C10 1.279(4)
O11 C11 1.215(5)
O13 C13 1.267(5)
O7 C7 1.263(5)
O8 C8 1.215(4)
N2 C5 1.498(5)
O9 C9 1.210(5)
O12 C12 1.214(4)
C14 C13 1.404(5)
C14 C11 1.466(5)
C10 C7 1.426(5)
C10 C9 1.445(5)
C8 C7 1.460(5)
C8 C9 1.509(5)
C13 C12 1.463(5)
C12 C11 1.499(5)
C5 C6 1.516(5)
C5 C4 1.520(5)
N1 C4 1.491(5)
C6 C1 1.504(7)
C4 C3 1.518(6)
C2 C3 1.496(6)
C2 C1 1.524(7)
