#------------------------------------------------------------------------------
#$Date: 2014-07-11 19:31:04 +0200 (Fri, 11 Jul 2014) $
#$Revision: 120073 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/15/4001513.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_4001513
loop_
_publ_author_name
'Prakash, M. Jaya'
'Radhakrishnan, T. P.'
_publ_section_title
;
 Second Harmonic Generation from a Homologous Series of Molecular
 Crystals: Impact of Supramolecular Interactions
;
_journal_issue                   13
_journal_name_full               'Chemistry of Materials'
_journal_page_first              2943
_journal_volume                  18
_journal_year                    2006
_chemical_formula_sum            'C9 H13 N3 O4'
_chemical_formula_weight         227.22
_chemical_name_systematic
'N-(2-aminoethyl)-4-nitroaniline formic acid (salt)'
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   12.2752(13)
_cell_length_b                   8.2530(8)
_cell_length_c                   22.052(2)
_cell_measurement_temperature    298(2)
_cell_volume                     2234.0(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.1059
_diffrn_reflns_av_sigmaI/netI    0.0662
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            24049
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9883
_exptl_absorpt_correction_T_min  0.7777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-Bruker Nonius area detector scaling and absorption correction - V2.10'
_exptl_crystal_colour            'Light yellow'
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.14
_refine_diff_density_rms         0.03
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1426
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0489
_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/[\s^2^(Fo^2^)+(0.0469P)^2^+0.2629P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1136
_reflns_number_gt                1272
_reflns_number_total             2735
_reflns_threshold_expression     >2sigma(I)
_[local]_cod_data_source_file    cm052607qsi20051126_120337.cif
_[local]_cod_data_source_block   AENA_for
_[local]_cod_cif_authors_sg_H-M  Pbca
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               4001513
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'
'-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
O2 O 0.32721(13) 0.1977(2) 0.70849(8) 0.0558(5) Uani 1 1 d .
O1 O 0.49767(14) 0.2138(2) 0.74110(8) 0.0602(5) Uani 1 1 d .
N1 N 1.14335(19) 0.3685(3) 0.68369(10) 0.0482(6) Uani 1 1 d .
C4 C 0.8469(2) 0.4826(3) 0.61537(11) 0.0450(6) Uani 1 1 d .
N2 N 0.95107(18) 0.5188(3) 0.63214(11) 0.0556(6) Uani 1 1 d .
C3 C 0.7605(2) 0.5333(3) 0.65227(11) 0.0482(6) Uani 1 1 d .
H32 H 0.7756 0.5892 0.6879 0.058 Uiso 1 1 calc R
N3 N 0.5209(2) 0.3880(3) 0.56663(13) 0.0656(7) Uani 1 1 d .
O4 O 0.50356(18) 0.3139(2) 0.51917(11) 0.0863(7) Uani 1 1 d .
C5 C 0.8215(2) 0.3963(3) 0.56234(11) 0.0533(7) Uani 1 1 d .
H25 H 0.8773 0.3584 0.5376 0.064 Uiso 1 1 calc R
C9 C 0.4065(2) 0.2702(4) 0.73082(12) 0.0519(7) Uani 1 1 d .
C2 C 0.6546(2) 0.5027(3) 0.63715(12) 0.0501(7) Uani 1 1 d .
H2 H 0.5982 0.5362 0.6623 0.060 Uiso 1 1 calc R
O3 O 0.44719(18) 0.4355(3) 0.60001(11) 0.0825(7) Uani 1 1 d .
C8 C 1.1153(2) 0.3507(3) 0.61876(12) 0.0572(7) Uani 1 1 d .
H8A H 1.0748 0.2510 0.6129 0.069 Uiso 1 1 calc R
H8B H 1.1816 0.3440 0.5950 0.069 Uiso 1 1 calc R
C1 C 0.6327(2) 0.4208(3) 0.58367(12) 0.0498(7) Uani 1 1 d .
C7 C 1.0484(2) 0.4908(3) 0.59702(12) 0.0578(7) Uani 1 1 d .
H7A H 1.0929 0.5878 0.5980 0.069 Uiso 1 1 calc R
H7B H 1.0279 0.4716 0.5552 0.069 Uiso 1 1 calc R
C6 C 0.7161(2) 0.3678(3) 0.54699(12) 0.0587(7) Uani 1 1 d .
H6 H 0.7001 0.3120 0.5114 0.070 Uiso 1 1 calc R
H3 H 1.1546(19) 0.478(4) 0.6953(11) 0.063(8) Uiso 1 1 d .
H1 H 0.3952(18) 0.384(3) 0.7390(10) 0.057(8) Uiso 1 1 d .
H5 H 1.085(3) 0.322(4) 0.7113(14) 0.097(10) Uiso 1 1 d .
H4 H 1.212(2) 0.310(3) 0.6918(12) 0.083(9) Uiso 1 1 d .
H24 H 0.957(2) 0.571(3) 0.6654(13) 0.068(9) Uiso 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
O2 0.0392(10) 0.0541(11) 0.0741(12) -0.0038(10) -0.0069(9) 0.0031(9)
O1 0.0428(10) 0.0687(12) 0.0691(13) -0.0143(10) -0.0074(9) 0.0046(10)
N1 0.0389(13) 0.0455(14) 0.0602(16) 0.0045(12) 0.0031(11) 0.0039(11)
C4 0.0554(17) 0.0427(14) 0.0368(14) 0.0026(12) -0.0062(12) 0.0057(12)
N2 0.0487(14) 0.0736(16) 0.0447(14) -0.0106(12) -0.0039(11) 0.0104(12)
C3 0.0518(17) 0.0533(16) 0.0395(15) -0.0087(12) -0.0042(13) 0.0067(13)
N3 0.0704(19) 0.0547(15) 0.0717(19) 0.0133(14) -0.0168(15) -0.0151(14)
O4 0.1030(17) 0.0803(15) 0.0756(16) -0.0010(13) -0.0368(13) -0.0345(12)
C5 0.0615(18) 0.0545(16) 0.0438(15) -0.0061(13) 0.0034(13) 0.0007(14)
C9 0.0511(18) 0.0484(18) 0.0562(18) -0.0077(14) 0.0060(14) 0.0042(14)
C2 0.0505(17) 0.0517(16) 0.0480(16) 0.0005(13) -0.0009(13) 0.0031(13)
O3 0.0584(14) 0.0918(17) 0.0974(17) 0.0102(14) -0.0089(12) -0.0107(12)
C8 0.0547(17) 0.0600(17) 0.0570(18) -0.0062(15) 0.0057(14) 0.0061(14)
C1 0.0585(17) 0.0430(15) 0.0480(16) 0.0060(12) -0.0133(14) -0.0107(13)
C7 0.0548(17) 0.0685(18) 0.0501(17) 0.0032(14) 0.0012(13) 0.0038(15)
C6 0.078(2) 0.0550(17) 0.0429(16) -0.0100(13) -0.0044(15) -0.0086(15)
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
N2 C4 C3 119.1(2)
N2 C4 C5 123.0(2)
C3 C4 C5 117.8(2)
C4 N2 C7 126.6(2)
C2 C3 C4 121.6(2)
O3 N3 O4 122.6(3)
O3 N3 C1 118.9(3)
O4 N3 C1 118.5(3)
C6 C5 C4 120.5(2)
O1 C9 O2 127.0(3)
C3 C2 C1 118.9(2)
N1 C8 C7 111.2(2)
C6 C1 C2 120.7(2)
C6 C1 N3 119.5(3)
C2 C1 N3 119.7(3)
N2 C7 C8 114.0(2)
C5 C6 C1 120.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C9 1.244(3)
O1 C9 1.233(3)
N1 C8 1.480(3)
C4 N2 1.364(3)
C4 C3 1.401(3)
C4 C5 1.404(3)
N2 C7 1.443(3)
C3 C2 1.366(3)
N3 O3 1.231(3)
N3 O4 1.231(3)
N3 C1 1.447(3)
C5 C6 1.359(3)
C2 C1 1.386(3)
C8 C7 1.496(3)
C1 C6 1.376(4)
_journal_paper_doi 10.1021/cm052607q