#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/49/7204934.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_7204934
loop_
_publ_author_name
'Langley, Philip J.'
'Bailey, Ray T.'
'Cruickshank, Frank R.'
'Kennedy, Alan R.'
'Lochran, Stephen'
'Pugh, David'
'Sherwood, John N.'
'Viikki, Anna'
'Wallis, John D.'
_publ_section_title
;
 Synthesis, characterisation and structure--property analysis of
 derivatives of the non-linear optical material
 5-nitro-N-(1-phenylethyl)pyridin-2-amine
;
_journal_issue                   4
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              1047
_journal_paper_doi               10.1039/b008124h
_journal_volume                  11
_journal_year                    2001
_chemical_formula_sum            'C14 H15 N3 O2'
_chemical_formula_weight         257.29
_chemical_melting_point          318.5(5)
_chemical_name_systematic
;
 ?
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.481(4)
_cell_length_b                   6.791(8)
_cell_length_c                   35.877(29)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.94
_cell_measurement_theta_min      2.27
_cell_volume                     1335(2)
_computing_cell_refinement       'REFINE (incorporated in MADNES)'
_computing_data_collection       'MADNES (Pflugrath & Messerschmidt,1989)''
_computing_data_reduction        'ABSMAD (Karaulov, 1991)'
_computing_publication_material  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measurement_device       'Delft Instruments FAST-TV area- detector''
_diffrn_measurement_method       'Darr et al. (1993)'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.1208
_diffrn_reflns_av_sigmaI/netI    0.0966
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            4474
_diffrn_reflns_theta_max         24.94
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        'not measured'
_diffrn_standards_interval_count 'not measured'
_diffrn_standards_interval_time  'not measured'
_diffrn_standards_number         'not measured'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       rod
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.30(330)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.234
_refine_ls_goodness_of_fit_obs   1.318
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         1820
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.254
_refine_ls_restrained_S_obs      1.318
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_obs          0.0573
_refine_ls_shift/esd_max         -0.002
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1099P)²+0.0318P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1794
_refine_ls_wR_factor_obs         0.1718
_reflns_number_observed          1562
_reflns_number_total             1842
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b008124h.txt
_cod_data_source_block           compound_(S)-2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '318-319' was changed to '318.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_cell_volume        1335.4(21)
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7204934
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
O1 O 0.4808(7) 0.8553(5) 0.03156(8) 0.0502(9) Uani 1 d . .
O2 O 0.2310(9) 0.8333(5) 0.07802(12) 0.0746(13) Uani 1 d . .
N1 N 0.5095(7) 0.3103(5) 0.11124(9) 0.0315(8) Uani 1 d . .
N2 N 0.8045(7) 0.0703(5) 0.10626(9) 0.0318(8) Uani 1 d . .
N5 N 0.3973(7) 0.7669(5) 0.05840(10) 0.0398(10) Uani 1 d . .
C2 C 0.7008(8) 0.2361(6) 0.09211(10) 0.0278(9) Uani 1 d . .
C3 C 0.7973(8) 0.3240(6) 0.05910(10) 0.0288(9) Uani 1 d . .
C4 C 0.6965(8) 0.5006(6) 0.04797(11) 0.0329(10) Uani 1 d . .
C5 C 0.5032(9) 0.5794(5) 0.06891(10) 0.0313(9) Uani 1 d . .
C6 C 0.4123(9) 0.4800(6) 0.09959(11) 0.0344(10) Uani 1 d . .
C7 C 0.7327(9) -0.0115(6) 0.14235(10) 0.0295(10) Uani 1 d . .
C8 C 0.8670(11) -0.2073(7) 0.14875(13) 0.0431(12) Uani 1 d . .
C31 C 0.9973(10) 0.2264(7) 0.03714(12) 0.0377(10) Uani 1 d . .
C1' C 0.7843(8) 0.1293(6) 0.17431(10) 0.0300(9) Uani 1 d . .
C2' C 0.6206(8) 0.1401(7) 0.20421(11) 0.0353(10) Uani 1 d . .
C3' C 0.6678(9) 0.2620(7) 0.23442(11) 0.0402(11) Uani 1 d . .
C4' C 0.8784(9) 0.3765(7) 0.23536(12) 0.0416(11) Uani 1 d . .
C5' C 1.0412(9) 0.3666(7) 0.20603(12) 0.0383(10) Uani 1 d . .
C6' C 0.9955(9) 0.2432(6) 0.17590(12) 0.0342(10) Uani 1 d . .
H2 H 0.9313(95) 0.0284(59) 0.0954(12) 0.026(11) Uiso 1 d . .
H4 H 0.7525(76) 0.5720(51) 0.0240(10) 0.019(9) Uiso 1 d . .
H6 H 0.2846(97) 0.5296(63) 0.1118(13) 0.037(12) Uiso 1 d . .
H71 H 0.5639(86) -0.0296(54) 0.1421(10) 0.022(10) Uiso 1 d . .
H81 H 1.0569(129) -0.1797(76) 0.1501(15) 0.059(16) Uiso 1 d . .
H82 H 0.8170(97) -0.2672(73) 0.1743(15) 0.051(14) Uiso 1 d . .
H83 H 0.8326(106) -0.2995(84) 0.1286(17) 0.060(15) Uiso 1 d . .
H311 H 1.0342(76) 0.3013(56) 0.0170(12) 0.023(10) Uiso 1 d . .
H312 H 1.1486(104) 0.2181(78) 0.0544(16) 0.059(16) Uiso 1 d . .
H313 H 0.9579(111) 0.0957(95) 0.0277(16) 0.065(17) Uiso 1 d . .
H21' H 0.4538(105) 0.0684(77) 0.2007(14) 0.055(15) Uiso 1 d . .
H31' H 0.5461(79) 0.2704(52) 0.2548(11) 0.022(9) Uiso 1 d . .
H41' H 0.9006(78) 0.4673(62) 0.2561(13) 0.031(11) Uiso 1 d . .
H51' H 1.1977(98) 0.4339(76) 0.2034(13) 0.049(13) Uiso 1 d . .
H61' H 1.0958(123) 0.2381(92) 0.1587(19) 0.072(19) Uiso 1 d . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C2 118.2(3) . . ?
C2 N2 C7 122.2(3) . . ?
O1 N5 O2 123.0(4) . . ?
O1 N5 C5 119.1(4) . . ?
O2 N5 C5 117.8(4) . . ?
N1 C2 N2 116.3(3) . . ?
N1 C2 C3 123.6(4) . . ?
N2 C2 C3 120.0(4) . . ?
C4 C3 C2 117.1(4) . . ?
C4 C3 C31 121.6(4) . . ?
C2 C3 C31 121.4(3) . . ?
C3 C4 C5 118.6(4) . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 N5 119.4(4) . . ?
C4 C5 N5 119.8(3) . . ?
N1 C6 C5 121.7(4) . . ?
N2 C7 C1' 112.3(3) . . ?
N2 C7 C8 109.4(3) . . ?
C1' C7 C8 110.0(3) . . ?
C6' C1' C2' 118.2(4) . . ?
C6' C1' C7 122.3(4) . . ?
C2' C1' C7 119.5(4) . . ?
C3' C2' C1' 120.7(4) . . ?
C2' C3' C4' 120.4(4) . . ?
C5' C4' C3' 119.3(4) . . ?
C4' C5' C6' 120.4(4) . . ?
C5' C6' C1' 121.1(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N5 1.223(5) . ?
O2 N5 1.237(5) . ?
N1 C6 1.337(5) . ?
N1 C2 1.350(5) . ?
N2 C2 1.360(5) . ?
N2 C7 1.463(5) . ?
N5 C5 1.449(5) . ?
C2 C3 1.428(6) . ?
C3 C4 1.380(6) . ?
C3 C31 1.504(6) . ?
C4 C5 1.405(6) . ?
C5 C6 1.384(6) . ?
C7 C1' 1.520(6) . ?
C7 C8 1.537(6) . ?
C1' C6' 1.393(6) . ?
C1' C2' 1.400(6) . ?
C2' C3' 1.388(7) . ?
C3' C4' 1.392(7) . ?
C4' C5' 1.381(7) . ?
C5' C6' 1.390(6) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 6216640
