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#$Date: 2018-01-30 16:30:45 +0200 (Tue, 30 Jan 2018) $
#$Revision: 205898 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/12/2101286.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2101286
loop_
_publ_author_name
'Fkyerat, A.'
'Guelzim, A.'
'Baert, E.'
'Paulus, W.'
'Heger, G.'
'Zyss, J.'
'Périgaud, A.'
_publ_section_title
;
 Electron density study by X-ray and neutron diffraction of an NLO
 compound: N-(4-nitrophenyl)-<small>L</small>-prolinol.
 Description of quadratic hyperpolarizability
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              197
_journal_page_last               209
_journal_paper_doi               10.1107/S0108768194007391
_journal_volume                  51
_journal_year                    1995
_chemical_formula_sum            'C11 H14 N2 O3'
_chemical_formula_weight         222.2
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_cell_angle_alpha                90
_cell_angle_beta                 105.86(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.164(2)
_cell_length_b                   14.796(8)
_cell_length_c                   7.108(5)
_cell_volume                     522.4(5)
_diffrn_radiation_probe          neutron
_diffrn_radiation_type           neutron
_diffrn_radiation_wavelength     0.8308
_exptl_absorpt_coefficient_mu    0.084
_exptl_crystal_density_diffrn    1.41
_exptl_crystal_F_000             236
_cod_data_source_file            pa0296.cif
_cod_data_source_block           pa0296b
_cod_depositor_comments
;
 Adding the _atom_site_type_symbol data item.

 Antanas Vaitkus,
 2017-01-18
;
_cod_original_cell_volume        522.4
_cod_database_code               2101286
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
C(1) C .5190(7) .0455 .4387(7)
C(2) C .5365(7) .1388(4) .4553(7)
C(3) C .6648(7) .1881(5) .3440(6)
C(4) C .7806(7) .1436(3) .2102(6)
C(5) C .7632(7) .0486(4) .1981(6)
C(6) C .6356(6) -.0004(5) .3114(6)
C(7) C .8729(6) .2892(4) .0647(6)
C(8) C .9030(6) .3007(4) -.1401(6)
C(9) C 1.0946(7) .2258(5) -.1587(7)
C(10) C 1.0070(7) .1472(4) -.0518(7)
C(11) C 1.0903(6) .3404(4) .2160(6)
N(1) N .3851(5) -.0045(4) .5570(5)
N(2) N .8986(4) .1912(4) .0949(4)
O(1) O .3515(9) -.0857(5) .5319(8)
O(2) O .3042(10) .0376(5) .6777(11)
O(3) O 1.0696(8) .4346(5) .1830(8)
HC(2) H .4457(15) .1726(9) .5573(15)
HC(3) H .6798(17) .2597(7) .3611(15)
HC(5) H .8481(18) .0126(9) .0935(19)
HC(6) H .6233(19) -.0727(8) .3051(17)
HC(7) H .6748(12) .3121(7) .0754(12)
HC(8) H .7109(14) .2915(8) -.2462(13)
HC(8') H .9720(18) .3672(8) -.1649(16)
HC(9) H 1.3016(13) .2444(9) -.0851(15)
HC(9') H 1.0872(17) .2068(9) -.3125(16)
HC(10) H 1.1756(13) .1011(8) .0172(15)
HC(10') H .8513(14) .1057(8) -.1509(13)
HC(11) H 1.2883(12) .3189(7) .2059(15)
HC(11') H 1.0797(16) .3264(8) .3684(14)
HO(3) H .9243(15) .4580(8) .2282(16)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(2) C(1) C(6) 120.7(4)
C(11) C(7) N(2) 111.6(4)
C(2) C(1) N(1) 119.7(3)
C(7) C(8) C(9) 104.0(4)
C(6) C(1) N(1) 119.6(3)
C(8) C(9) C(10) 103.0(4)
C(1) C(2) C(3) 120.7(4)
C(9) C(10) N(2) 103.8(4)
C(2) C(3) C(4) 120.1(4)
C(7) C(11) O(3) 111.4(4)
C(3) C(4) C(5) 118.2(4)
C(1) N(1) O(1) 119.7(4)
C(3) C(4) N(2) 120.7(4)
C(1) N(1) O(2) 117.5(4)
C(5) C(4) N(2) 121.1(4)
O(1) N(1) O(2) 122.9(5)
C(4) C(5) C(6) 121.4(4)
C(4) N(2) C(7) 124.6(4)
C(1) C(6) C(5) 119.0(4)
C(4) N(2) C(10) 121.7(4)
C(8) C(7) C(11) 111.8(4)
C(7) N(2) C(10) 111.9(3)
C(8) C(7) N(2) 102.9(4)
C(1) C(2) HC(2) 119.0(7)
C(3) C(2) HC(2) 120.3(7)
C(8) C(9) HC(9) 110.6(7)
C(8) C(9) HC(9') 114.8(7)
C(10) C(9) HC(9) 109.8(7)
C(10) C(9) HC(9') 111.1(6)
HC(9) C(9) HC(9') 107.4(9)
C(2) C(3) HC(3) 119.6(7)
C(4) C(3) HC(3) 120.5(7)
C(4) C(5) HC(5) 119.6(8)
C(6) C(5) HC(5) 119.0(8)
C(9) C(10) HC(10) 112.7(6)
C(9) C(10) HC(10') 111.8(6)
N(2) C(10) HC(10) 111.4(6)
N(2) C(10) HC(10') 110.4(6)
HC(10) C(10) HC(10') 106.8(8)
C(5) C(6) HC(6) 122.2(7)
C(1) C(6) HC(6) 118.8(7)
N(2) C(7) HC(7) 110.0(6)
C(8) C(7) HC(7) 111.9(6)
C(11) C(7) HC(7) 108.5(6)
C(7) C(8) HC(8) 110.0(6)
C(7) C(8) HC(8') 112.6(7)
C(9) C(8) HC(8) 110.2(6)
C(9) C(8) HC(8') 113.6(7)
HC(8) C(8) HC(8') 106.4(9)
C(7) C(11) HC(11) 109.3(6)
C(7) C(11) HC(11') 111.6(6)
O(3) C(11) HC(11) 107.9(7)
HC(11) C(11) HC(11') 107.7(8)
O(3) C(11) HC(11') 108.8(7)
C(11) O(3) HO(3) 109.3(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C(1) C(2) 1.386(5)
C(1) N(1) 1.432(5)
C(3) C(4) 1.416(6)
C(4) N(2) 1.345(5)
C(7) C(8) 1.516(6)
C(7) N(2) 1.467(8)
C(9) C(10) 1.524(7)
C(11) O(3) 1.413(8)
N(1) O(2) 1.223(7)
C(3) HC(3) 1.070(10)
C(6) HC(6) 1.070(10)
C(8) HC(8) 1.080(10)
C(9) HC(9) 1.090(10)
C(10) HC(10) 1.110(10)
C(11) HC(11) 1.090(10)
O(3) HO(3) 0.960(10)
C(1) C(6) 1.393(6)
C(2) C(3) 1.372(6)
C(4) C(5) 1.411(8)
C(5) C(6) 1.377(6)
C(7) C(11) 1.527(6)
C(8) C(9) 1.515(7)
C(10) N(2) 1.464(5)
N(1) O(1) 1.221(8)
C(2) HC(2) 1.090(10)
C(5) HC(5) 1.100(10)
C(7) HC(7) 1.100(10)
C(8) HC(8') 1.080(10)
C(9) HC(9') 1.120(10)
C(10) HC(10') 1.100(10)
C(11) HC(11') 1.120(10)
