#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:52:29 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179676 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/28/4512809.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_4512809
loop_
_publ_author_name
'Simon, Florent'
'Clevers, Simon'
'Gbabode, Gabin'
'Couvrat, Nicolas'
'Agasse-Peulon, Valérie'
'Sanselme, Morgane'
'Dupray, Valerie'
'Coquerel, Gerard'
_publ_section_title
;
 Enhanced Second Harmonic Generation from an Organic Self-Assembled
 Eutectic Binary Mixture: A Case Study with 3-Nitrobenzoic and
 3,5-Dinitrobenzoic Acids
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              946
_journal_paper_doi               10.1021/cg5017565
_journal_volume                  15
_journal_year                    2015
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C7 H4 N2 O6'
_chemical_formula_sum            'C7 H4 N2 O6'
_chemical_formula_weight         212.12
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2009-10-21T11:56:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 110.374(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.603(3)
_cell_length_b                   8.7468(15)
_cell_length_c                   9.7202(16)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_measurement_wavelength     0.71073
_cell_volume                     1642.1(5)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5100
_diffrn_reflns_theta_full        26.35
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            coulourless
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0579P)²+1.0972P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1068
_reflns_number_gt                1487
_reflns_number_total             1656
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            DNBA_C2-c_200K.CIF
_cod_data_source_block           ec11fm
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4512809
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.13465(7) -0.46136(15) -0.02548(15) 0.0294(3) Uani 1 1 d .
N2 N 0.02682(7) -0.19955(16) -0.49756(14) 0.0284(3) Uani 1 1 d .
O1 O 0.19468(6) 0.17941(12) -0.17759(12) 0.0324(3) Uani 1 1 d .
H1 H 0.2177 0.2533 -0.1359 0.049 Uiso 1 1 calc R
O2 O 0.23036(6) 0.08182(13) 0.05035(11) 0.0319(3) Uani 1 1 d .
O3 O 0.10349(8) -0.57648(14) -0.08320(15) 0.0458(4) Uani 1 1 d .
O4 O 0.17207(6) -0.45243(14) 0.10317(13) 0.0362(3) Uani 1 1 d .
O5 O -0.01931(6) -0.29557(16) -0.53168(13) 0.0417(3) Uani 1 1 d .
O6 O 0.03454(6) -0.10143(14) -0.57982(12) 0.0367(3) Uani 1 1 d .
C1 C 0.12671(8) -0.32440(17) -0.11852(17) 0.0246(3) Uani 1 1 d .
C2 C 0.08177(8) -0.33175(17) -0.26207(17) 0.0247(3) Uani 1 1 d .
H2 H 0.0569 -0.4199 -0.3007 0.03 Uiso 1 1 calc R
C3 C 0.07584(7) -0.20072(18) -0.34523(16) 0.0243(3) Uani 1 1 d .
C4 C 0.11341(7) -0.06926(17) -0.29133(16) 0.0238(3) Uani 1 1 d .
H4 H 0.1092 0.0159 -0.3511 0.029 Uiso 1 1 calc R
C5 C 0.15748(7) -0.06723(17) -0.14621(16) 0.0231(3) Uani 1 1 d .
C6 C 0.16418(8) -0.19499(18) -0.05739(16) 0.0232(3) Uani 1 1 d .
H6 H 0.1931 -0.1935 0.0405 0.028 Uiso 1 1 calc R
C7 C 0.19775(8) 0.07312(17) -0.08185(16) 0.0244(3) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0337(7) 0.0239(7) 0.0334(7) 0.0021(6) 0.0153(6) -0.0011(6)
N2 0.0262(7) 0.0326(7) 0.0258(7) -0.0048(6) 0.0084(5) -0.0005(5)
O1 0.0440(7) 0.0220(6) 0.0265(6) 0.0000(4) 0.0065(5) -0.0074(5)
O2 0.0402(6) 0.0289(6) 0.0237(6) -0.0026(5) 0.0076(5) -0.0091(5)
O3 0.0641(9) 0.0265(7) 0.0446(7) 0.0005(5) 0.0163(7) -0.0153(6)
O4 0.0436(7) 0.0327(7) 0.0305(6) 0.0076(5) 0.0108(5) 0.0022(5)
O5 0.0302(6) 0.0556(8) 0.0345(6) -0.0073(6) 0.0052(5) -0.0156(6)
O6 0.0428(7) 0.0391(7) 0.0247(6) 0.0027(5) 0.0075(5) -0.0012(6)
C1 0.0267(7) 0.0221(8) 0.0284(8) 0.0010(6) 0.0140(6) 0.0010(6)
C2 0.0250(7) 0.0233(7) 0.0292(8) -0.0051(6) 0.0138(6) -0.0038(6)
C3 0.0223(7) 0.0288(8) 0.0234(7) -0.0034(6) 0.0099(6) 0.0002(6)
C4 0.0245(7) 0.0240(7) 0.0246(7) 0.0015(6) 0.0108(6) 0.0005(6)
C5 0.0239(7) 0.0214(7) 0.0256(7) -0.0022(6) 0.0107(6) -0.0010(6)
C6 0.0235(7) 0.0254(8) 0.0213(7) -0.0023(6) 0.0083(6) 0.0008(6)
C7 0.0266(7) 0.0215(7) 0.0258(7) -0.0011(6) 0.0097(6) 0.0003(6)
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 0 '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 0.006 '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
O3 N1 O4 124.52(14)
O3 N1 C1 117.37(13)
O4 N1 C1 118.12(13)
O6 N2 O5 124.81(13)
O6 N2 C3 117.58(13)
O5 N2 C3 117.60(13)
C2 C1 C6 123.35(14)
C2 C1 N1 118.27(13)
C6 C1 N1 118.37(13)
C1 C2 C3 116.32(14)
C4 C3 C2 122.92(14)
C4 C3 N2 118.18(13)
C2 C3 N2 118.89(13)
C3 C4 C5 118.55(14)
C4 C5 C6 120.67(14)
C4 C5 C7 120.58(13)
C6 C5 C7 118.74(13)
C1 C6 C5 118.15(13)
O2 C7 O1 125.23(14)
O2 C7 C5 120.78(13)
O1 C7 C5 113.99(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 O3 1.2207(18)
N1 O4 1.2219(18)
N1 C1 1.475(2)
N2 O6 1.2206(18)
N2 O5 1.2244(18)
N2 C3 1.4736(19)
O1 C7 1.3013(18)
O2 C7 1.2277(18)
C1 C2 1.382(2)
C1 C6 1.382(2)
C2 C3 1.383(2)
C3 C4 1.383(2)
C4 C5 1.387(2)
C5 C6 1.389(2)
C5 C7 1.492(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.82 1.82 2.6357(16) 177.5 7
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
O3 N1 C1 C2 3.6(2)
O4 N1 C1 C2 -176.83(14)
O3 N1 C1 C6 -176.86(15)
O4 N1 C1 C6 2.7(2)
C6 C1 C2 C3 0.4(2)
N1 C1 C2 C3 179.90(13)
C1 C2 C3 C4 1.4(2)
C1 C2 C3 N2 -177.79(13)
O6 N2 C3 C4 19.1(2)
O5 N2 C3 C4 -159.82(14)
O6 N2 C3 C2 -161.66(14)
O5 N2 C3 C2 19.4(2)
C2 C3 C4 C5 -1.9(2)
N2 C3 C4 C5 177.31(13)
C3 C4 C5 C6 0.6(2)
C3 C4 C5 C7 -178.44(13)
C2 C1 C6 C5 -1.7(2)
N1 C1 C6 C5 178.84(12)
C4 C5 C6 C1 1.1(2)
C7 C5 C6 C1 -179.84(14)
C4 C5 C7 O2 171.29(14)
C6 C5 C7 O2 -7.7(2)
C4 C5 C7 O1 -9.0(2)
C6 C5 C7 O1 171.93(13)
