#------------------------------------------------------------------------------
#$Date: 2016-03-21 00:21:50 +0100 (Mon, 21 Mar 2016) $
#$Revision: 178377 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/15/4001516.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_4001516
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_paper_doi               10.1021/cm052607q
_journal_volume                  18
_journal_year                    2006
_chemical_formula_sum            'C12 H19 N3 O4'
_chemical_formula_weight         269.30
_chemical_name_systematic
'N-(2-aminoethyl)-4-nitroaniline butyric acid (salt)'
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 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                 99.521(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.8677(5)
_cell_length_b                   12.5586(13)
_cell_length_c                   11.3875(12)
_cell_measurement_temperature    298(2)
_cell_volume                     686.55(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_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  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0907
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7727
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_correction_T_min  0.7244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-Bruker Nonius area detector scaling and absorption correction - V2.10'
_exptl_crystal_colour            'Dark Orange'
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3185
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1562
_refine_ls_R_factor_gt           0.0596
_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^)+(0.0636P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1519
_reflns_number_gt                1551
_reflns_number_total             3185
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cm052607qsi20051126_120337.cif
_cod_data_source_block           AENA-but
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      Pc
_cod_database_code               4001516
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, 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
C12 C 0.1911(8) 0.6955(3) 1.0405(4) 0.0567(10) Uani 1 1 d .
H12A H 0.0715 0.7169 1.0966 0.068 Uiso 1 1 calc R
H12B H 0.3683 0.7317 1.0623 0.068 Uiso 1 1 calc R
N3 N 0.2368(7) 0.5782(3) 1.0491(3) 0.0458(8) Uani 1 1 d .
O2 O 0.4140(6) 0.4973(2) 0.7782(2) 0.0593(7) Uani 1 1 d .
O1 O 0.6880(5) 0.5073(2) 0.9526(2) 0.0590(7) Uani 1 1 d .
N1 N 0.7486(8) 1.0392(4) 0.6022(4) 0.0728(11) Uani 1 1 d .
C5 C 0.3355(8) 0.9058(3) 0.8068(4) 0.0592(11) Uani 1 1 d .
H5 H 0.2322 0.9243 0.8655 0.071 Uiso 1 1 calc R
C6 C 0.3636(7) 0.7997(3) 0.7779(3) 0.0502(10) Uani 1 1 d .
C8 C 0.6194(8) 0.4669(3) 0.8506(4) 0.0485(10) Uani 1 1 d .
C7 C 0.0612(9) 0.7285(3) 0.9182(4) 0.0635(11) Uani 1 1 d .
H7A H -0.1033 0.6853 0.8932 0.076 Uiso 1 1 calc R
H7B H 0.0015 0.8020 0.9205 0.076 Uiso 1 1 calc R
O4 O 0.7055(9) 1.1325(3) 0.6245(4) 0.1087(13) Uani 1 1 d .
O3 O 0.8950(8) 1.0111(3) 0.5312(4) 0.1008(12) Uani 1 1 d .
N2 N 0.2428(7) 0.7186(3) 0.8311(3) 0.0629(11) Uani 1 1 d .
C2 C 0.6528(9) 0.8534(4) 0.6382(4) 0.0632(12) Uani 1 1 d .
H2A H 0.7654 0.8358 0.5826 0.076 Uiso 1 1 calc R
C4 C 0.4603(9) 0.9845(4) 0.7488(4) 0.0669(12) Uani 1 1 d .
H4A H 0.4375 1.0558 0.7673 0.080 Uiso 1 1 calc R
C3 C 0.6160(8) 0.9574(4) 0.6651(4) 0.0566(11) Uani 1 1 d .
C1 C 0.5272(9) 0.7754(3) 0.6916(4) 0.0609(11) Uani 1 1 d .
H1 H 0.5498 0.7047 0.6706 0.073 Uiso 1 1 calc R
C9 C 0.7931(9) 0.3772(4) 0.8157(4) 0.0689(13) Uani 1 1 d .
H9A H 0.6696 0.3278 0.7671 0.083 Uiso 1 1 calc R
H9B H 0.9178 0.4063 0.7657 0.083 Uiso 1 1 calc R
C11 C 1.0998(12) 0.2169(4) 0.8772(6) 0.1060(19) Uani 1 1 d .
H11A H 0.9618 0.1701 0.8349 0.159 Uiso 1 1 calc R
H11B H 1.1931 0.1818 0.9475 0.159 Uiso 1 1 calc R
H11C H 1.2330 0.2352 0.8271 0.159 Uiso 1 1 calc R
C10 C 0.9614(15) 0.3162(4) 0.9118(5) 0.1021(18) Uani 1 1 d .
H10A H 0.8424 0.2967 0.9688 0.123 Uiso 1 1 calc R
H10B H 1.1050 0.3630 0.9525 0.123 Uiso 1 1 calc R
H2 H 0.081(8) 0.544(3) 1.015(3) 0.041(10) Uiso 1 1 d .
H1A H 0.301(8) 0.557(3) 1.128(4) 0.050(11) Uiso 1 1 d .
H3 H 0.282(9) 0.659(4) 0.813(4) 0.063(15) Uiso 1 1 d .
H4 H 0.395(10) 0.559(3) 1.005(4) 0.082(14) 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
C12 0.063(3) 0.053(3) 0.059(2) 0.000(2) 0.022(2) -0.002(2)
N3 0.0432(19) 0.054(2) 0.0416(19) -0.0020(17) 0.0124(17) -0.0013(17)
O2 0.0608(16) 0.0582(18) 0.0577(16) -0.0119(13) 0.0065(14) 0.0084(14)
O1 0.0516(15) 0.0728(18) 0.0548(17) -0.0173(13) 0.0152(12) -0.0004(13)
N1 0.068(3) 0.075(3) 0.075(3) 0.018(2) 0.011(2) -0.002(2)
C5 0.058(3) 0.060(3) 0.061(3) -0.003(2) 0.017(2) 0.009(2)
C6 0.050(2) 0.046(3) 0.053(2) 0.008(2) 0.0041(18) 0.0045(19)
C8 0.047(2) 0.053(2) 0.050(2) -0.0047(19) 0.022(2) -0.0055(19)
C7 0.067(3) 0.057(3) 0.073(3) 0.010(2) 0.028(2) 0.008(2)
O4 0.120(3) 0.060(2) 0.152(4) 0.018(2) 0.037(3) -0.012(2)
O3 0.099(3) 0.116(3) 0.097(3) 0.033(2) 0.042(2) -0.004(2)
N2 0.078(3) 0.048(3) 0.068(3) 0.004(2) 0.0299(19) 0.011(2)
C2 0.070(3) 0.066(3) 0.057(3) 0.013(3) 0.019(2) 0.006(2)
C4 0.068(3) 0.048(3) 0.085(3) 0.003(2) 0.011(3) -0.002(2)
C3 0.051(2) 0.055(3) 0.063(3) 0.012(2) 0.007(2) 0.000(2)
C1 0.079(3) 0.053(3) 0.053(2) 0.000(2) 0.018(2) 0.008(2)
C9 0.068(3) 0.076(3) 0.063(3) -0.010(2) 0.011(2) 0.019(2)
C11 0.122(5) 0.091(4) 0.104(4) 0.001(3) 0.015(4) 0.031(3)
C10 0.138(5) 0.079(4) 0.094(4) 0.005(3) 0.034(4) 0.023(4)
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 C12 N3 111.8(3)
O3 N1 O4 123.7(5)
O3 N1 C3 118.5(4)
O4 N1 C3 117.8(4)
C4 C5 C6 120.4(4)
N2 C6 C5 123.0(4)
N2 C6 C1 119.1(4)
C5 C6 C1 117.9(4)
O2 C8 O1 123.1(3)
O2 C8 C9 118.7(3)
O1 C8 C9 118.1(3)
N2 C7 C12 114.0(4)
C6 N2 C7 126.9(4)
C1 C2 C3 120.6(4)
C3 C4 C5 119.8(4)
C4 C3 C2 120.6(4)
C4 C3 N1 120.7(4)
C2 C3 N1 118.6(4)
C2 C1 C6 120.7(4)
C10 C9 C8 117.6(4)
C9 C10 C11 117.2(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C12 C7 1.490(6)
C12 N3 1.491(5)
O2 C8 1.246(5)
O1 C8 1.262(4)
N1 O3 1.216(5)
N1 O4 1.224(5)
N1 C3 1.462(6)
C5 C4 1.384(6)
C5 C6 1.385(5)
C6 N2 1.367(5)
C6 C1 1.397(6)
C8 C9 1.500(5)
C7 N2 1.439(5)
C2 C1 1.351(6)
C2 C3 1.361(6)
C4 C3 1.356(6)
C9 C10 1.470(6)
C11 C10 1.501(7)