#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:11:47 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180380 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/49/7204936.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_7204936
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          372.0(10)
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 96.520(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9790(10)
_cell_length_b                   15.977(2)
_cell_length_c                   9.410(2)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.88
_cell_measurement_theta_min      2.18
_cell_volume                     1341.2(4)
_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      293(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  0.1075
_diffrn_reflns_av_sigmaI/netI    0.0907
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5980
_diffrn_reflns_theta_max         24.88
_diffrn_reflns_theta_min         2.18
_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    1.274
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.54(152)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.942
_refine_ls_goodness_of_fit_obs   1.029
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         3687
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.089
_refine_ls_restrained_S_obs      1.029
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_obs          0.0481
_refine_ls_shift/esd_max         -0.004
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0579P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1351
_refine_ls_wR_factor_obs         0.1101
_reflns_number_observed          2870
_reflns_number_total             3752
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b008124h.txt
_cod_data_source_block           compound_6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '371-373' was changed to '372.0(10)'
- 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_sg_symbol_H-M      P21
_cod_database_code               7204936
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
_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
O1A O 0.6841(3) -0.0146(2) 0.2447(3) 0.0982(9) Uani 1 d . .
O2A O 0.6767(3) -0.1322(2) 0.3582(3) 0.0875(8) Uani 1 d . .
N1A N 0.4435(3) -0.0303(2) 0.6591(3) 0.0596(7) Uani 1 d . .
N2A N 0.3333(3) 0.08453(14) 0.7540(3) 0.0560(7) Uani 1 d . .
N5A N 0.6459(3) -0.0580(2) 0.3426(3) 0.0676(8) Uani 1 d . .
C2A C 0.4061(3) 0.0510(2) 0.6481(3) 0.0499(8) Uani 1 d . .
C3A C 0.4408(4) 0.0999(2) 0.5323(4) 0.0591(9) Uani 1 d . .
H3A H 0.4116(4) 0.1557(2) 0.5252(4) 0.071 Uiso 1 calc R .
C4A C 0.5183(4) 0.0647(2) 0.4295(3) 0.0619(9) Uani 1 d . .
H4A H 0.5430(4) 0.0961(2) 0.3523(3) 0.074 Uiso 1 calc R .
C5A C 0.5582(3) -0.0181(2) 0.4441(3) 0.0547(8) Uani 1 d . .
C6A C 0.5182(4) -0.0637(2) 0.5569(3) 0.0624(9) Uani 1 d . .
H6A H 0.5439(4) -0.1201(2) 0.5632(3) 0.075 Uiso 1 calc R .
C7A C 0.2983(4) 0.0351(2) 0.8784(3) 0.0575(8) Uani 1 d . .
H7A H 0.3299(4) -0.0225(2) 0.8623(3) 0.069 Uiso 1 calc R .
C8A C 0.3891(5) 0.0649(3) 1.0161(4) 0.0863(11) Uani 1 d . .
H8A1 H 0.4938(5) 0.0646(3) 1.0039(4) 0.130 Uiso 1 calc R .
H8A2 H 0.3716(5) 0.0282(3) 1.0932(4) 0.130 Uiso 1 calc R .
H8A3 H 0.3590(5) 0.1207(3) 1.0377(4) 0.130 Uiso 1 calc R .
C9A C 0.2884(4) 0.1716(2) 0.7489(4) 0.0748(10) Uani 1 d . .
H9A1 H 0.2388(4) 0.1845(2) 0.8313(4) 0.112 Uiso 1 calc R .
H9A2 H 0.2211(4) 0.1815(2) 0.6637(4) 0.112 Uiso 1 calc R .
H9A3 H 0.3754(4) 0.2064(2) 0.7481(4) 0.112 Uiso 1 calc R .
C1'A C 0.1294(4) 0.0328(2) 0.8839(3) 0.0567(8) Uani 1 d . .
C2'A C 0.0409(5) -0.0129(3) 0.7810(4) 0.0766(10) Uani 1 d . .
H2'A H 0.0869(5) -0.0411(3) 0.7113(4) 0.092 Uiso 1 calc R .
C3'A C -0.1092(5) -0.0179(3) 0.7785(5) 0.0971(13) Uani 1 d . .
H3'A H -0.1649(5) -0.0495(3) 0.7083(5) 0.117 Uiso 1 calc R .
C4'A C -0.1792(5) 0.0233(3) 0.8790(6) 0.1005(14) Uani 1 d . .
H4'A H -0.2829(5) 0.0203(3) 0.8766(6) 0.121 Uiso 1 calc R .
C5'A C -0.0991(6) 0.0682(3) 0.9815(6) 0.1022(15) Uani 1 d . .
H5'A H -0.1476(6) 0.0958(3) 1.0501(6) 0.123 Uiso 1 calc R .
C6'A C 0.0571(5) 0.0738(3) 0.9856(4) 0.0812(11) Uani 1 d . .
H6'A H 0.1120(5) 0.1050(3) 1.0568(4) 0.097 Uiso 1 calc R .
O1B O 0.2955(3) 0.2937(2) 0.1260(3) 0.1026(10) Uani 1 d . .
O2B O 0.4551(3) 0.2504(2) 0.2975(3) 0.0811(8) Uani 1 d . .
N1B N 0.6190(3) 0.3413(2) -0.1293(2) 0.0574(7) Uani 1 d . .
N2B N 0.8678(3) 0.3355(2) -0.1713(3) 0.0582(7) Uani 1 d . .
N5B N 0.4247(3) 0.2797(2) 0.1777(3) 0.0626(7) Uani 1 d . .
C2B C 0.7631(3) 0.3245(2) -0.0797(3) 0.0486(7) Uani 1 d . .
C3B C 0.8036(4) 0.2969(2) 0.0626(3) 0.0600(8) Uani 1 d . .
H3B H 0.9037(4) 0.2887(2) 0.0972(3) 0.072 Uiso 1 calc R .
C4B C 0.6933(4) 0.2827(2) 0.1480(3) 0.0599(8) Uani 1 d . .
H4B H 0.7169(4) 0.2637(2) 0.2413(3) 0.072 Uiso 1 calc R .
C5B C 0.5459(4) 0.2968(2) 0.0936(3) 0.0523(7) Uani 1 d . .
C6B C 0.5142(4) 0.3275(2) -0.0429(3) 0.0555(8) Uani 1 d . .
H6B H 0.4149(4) 0.3391(2) -0.0765(3) 0.067 Uiso 1 calc R .
C7B C 0.8261(4) 0.3594(2) -0.3223(3) 0.0586(8) Uani 1 d . .
H7B H 0.7166(4) 0.3559(2) -0.3409(3) 0.070 Uiso 1 calc R .
C8B C 0.8691(5) 0.4497(2) -0.3459(4) 0.0799(11) Uani 1 d . .
H8B1 H 0.8239(5) 0.4851(2) -0.2805(4) 0.120 Uiso 1 calc R .
H8B2 H 0.8345(5) 0.4658(2) -0.4424(4) 0.120 Uiso 1 calc R .
H8B3 H 0.9761(5) 0.4553(2) -0.3300(4) 0.120 Uiso 1 calc R .
C9B C 1.0261(4) 0.3276(2) -0.1206(3) 0.0700(10) Uani 1 d . .
H9B1 H 1.0844(4) 0.3372(2) -0.1985(3) 0.105 Uiso 1 calc R .
H9B2 H 1.0458(4) 0.2723(2) -0.0833(3) 0.105 Uiso 1 calc R .
H9B3 H 1.0527(4) 0.3680(2) -0.0467(3) 0.105 Uiso 1 calc R .
C1'B C 0.8903(3) 0.2961(2) -0.4193(3) 0.0551(8) Uani 1 d . .
C2'B C 0.9969(4) 0.3158(2) -0.5078(3) 0.0607(8) Uani 1 d . .
H2'B H 1.0328(4) 0.3703(2) -0.5093(3) 0.073 Uiso 1 calc R .
C3'B C 1.0523(4) 0.2555(3) -0.5955(4) 0.0755(11) Uani 1 d . .
H3'B H 1.1246(4) 0.2699(3) -0.6546(4) 0.091 Uiso 1 calc R .
C4'B C 1.0000(6) 0.1758(3) -0.5942(5) 0.0883(13) Uani 1 d . .
H4'B H 1.0367(6) 0.1355(3) -0.6526(5) 0.106 Uiso 1 calc R .
C5'B C 0.8944(6) 0.1544(3) -0.5081(5) 0.0962(13) Uani 1 d . .
H5'B H 0.8587(6) 0.0998(3) -0.5084(5) 0.115 Uiso 1 calc R .
C6'B C 0.8401(5) 0.2135(3) -0.4203(4) 0.0805(11) Uani 1 d . .
H6'B H 0.7688(5) 0.1980(3) -0.3609(4) 0.097 Uiso 1 calc R .
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
C2A N1A C6A 118.0(3) . . ?
C2A N2A C9A 120.6(3) . . ?
C2A N2A C7A 122.2(2) . . ?
C9A N2A C7A 117.2(3) . . ?
O2A N5A O1A 123.9(3) . . ?
O2A N5A C5A 118.7(3) . . ?
O1A N5A C5A 117.5(3) . . ?
N1A C2A N2A 117.5(2) . . ?
N1A C2A C3A 121.5(3) . . ?
N2A C2A C3A 121.0(3) . . ?
C4A C3A C2A 119.6(3) . . ?
C5A C4A C3A 118.1(3) . . ?
C6A C5A C4A 120.1(3) . . ?
C6A C5A N5A 119.0(3) . . ?
C4A C5A N5A 120.8(3) . . ?
N1A C6A C5A 122.7(3) . . ?
N2A C7A C1'A 110.0(2) . . ?
N2A C7A C8A 111.4(3) . . ?
C1'A C7A C8A 114.6(3) . . ?
C6'A C1'A C2'A 117.1(3) . . ?
C6'A C1'A C7A 124.0(3) . . ?
C2'A C1'A C7A 118.8(3) . . ?
C3'A C2'A C1'A 122.4(4) . . ?
C2'A C3'A C4'A 119.8(4) . . ?
C5'A C4'A C3'A 120.4(4) . . ?
C4'A C5'A C6'A 120.4(4) . . ?
C1'A C6'A C5'A 119.9(4) . . ?
C6B N1B C2B 118.2(2) . . ?
C2B N2B C9B 120.2(2) . . ?
C2B N2B C7B 121.7(2) . . ?
C9B N2B C7B 118.0(2) . . ?
O2B N5B O1B 122.5(3) . . ?
O2B N5B C5B 118.4(3) . . ?
O1B N5B C5B 119.1(3) . . ?
N1B C2B N2B 117.4(2) . . ?
N1B C2B C3B 121.4(2) . . ?
N2B C2B C3B 121.2(3) . . ?
C4B C3B C2B 118.9(3) . . ?
C3B C4B C5B 118.9(3) . . ?
C6B C5B C4B 119.5(3) . . ?
C6B C5B N5B 119.4(3) . . ?
C4B C5B N5B 121.1(3) . . ?
N1B C6B C5B 123.0(3) . . ?
N2B C7B C8B 110.2(3) . . ?
N2B C7B C1'B 109.5(2) . . ?
C8B C7B C1'B 115.1(3) . . ?
C2'B C1'B C6'B 117.3(3) . . ?
C2'B C1'B C7B 123.3(3) . . ?
C6'B C1'B C7B 119.3(3) . . ?
C1'B C2'B C3'B 121.3(3) . . ?
C4'B C3'B C2'B 119.7(4) . . ?
C5'B C4'B C3'B 120.4(4) . . ?
C4'B C5'B C6'B 120.3(4) . . ?
C5'B C6'B C1'B 121.0(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
O1A N5A 1.233(4) . ?
O2A N5A 1.221(4) . ?
N1A C2A 1.342(4) . ?
N1A C6A 1.344(4) . ?
N2A C2A 1.362(4) . ?
N2A C9A 1.448(4) . ?
N2A C7A 1.475(4) . ?
N5A C5A 1.452(4) . ?
C2A C3A 1.405(4) . ?
C3A C4A 1.374(4) . ?
C4A C5A 1.373(5) . ?
C5A C6A 1.369(4) . ?
C7A C1'A 1.524(5) . ?
C7A C8A 1.526(5) . ?
C1'A C6'A 1.381(5) . ?
C1'A C2'A 1.388(5) . ?
C2'A C3'A 1.348(5) . ?
C3'A C4'A 1.364(6) . ?
C4'A C5'A 1.343(7) . ?
C5'A C6'A 1.402(6) . ?
O1B N5B 1.227(4) . ?
O2B N5B 1.223(3) . ?
N1B C6B 1.330(3) . ?
N1B C2B 1.352(4) . ?
N2B C2B 1.357(3) . ?
N2B C9B 1.452(4) . ?
N2B C7B 1.478(4) . ?
N5B C5B 1.442(4) . ?
C2B C3B 1.417(4) . ?
C3B C4B 1.364(4) . ?
C4B C5B 1.383(4) . ?
C5B C6B 1.374(4) . ?
C7B C8B 1.516(5) . ?
C7B C1'B 1.519(4) . ?
C1'B C2'B 1.375(4) . ?
C1'B C6'B 1.394(5) . ?
C2'B C3'B 1.396(5) . ?
C3'B C4'B 1.358(6) . ?
C4'B C5'B 1.358(6) . ?
C5'B C6'B 1.379(6) . ?
