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#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/49/7204937.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_7204937
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_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 91.149(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9781(11)
_cell_length_b                   22.337(4)
_cell_length_c                   8.3899(12)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.52
_cell_measurement_theta_min      20.86
_cell_volume                     1307.5(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  AFC7S
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0106
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3401
_diffrn_reflns_theta_full        28.01
_diffrn_reflns_theta_max         28.01
_diffrn_reflns_theta_min         2.59
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3159
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0298P)²+0.4067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1188
_reflns_number_gt                2253
_reflns_number_total             3159
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b008124h.txt
_cod_data_source_block           racemic_compound_2
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7204937
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2150(2) 0.38747(6) 0.54607(19) 0.0785(4) Uani 1 d . . .
O2 O 0.0235(2) 0.31657(7) 0.6121(2) 0.0873(5) Uani 1 d . . .
N5 N 0.1702(2) 0.33441(7) 0.54918(18) 0.0582(4) Uani 1 d . . .
N1 N 0.37133(18) 0.18882(6) 0.43412(16) 0.0496(3) Uani 1 d . . .
N2 N 0.63826(19) 0.16384(5) 0.29209(16) 0.0463(3) Uani 1 d . . .
C6 C 0.2584(2) 0.23095(8) 0.4938(2) 0.0521(4) Uani 1 d . . .
C5 C 0.2950(2) 0.29121(7) 0.47721(18) 0.0463(4) Uani 1 d . . .
C4 C 0.4562(2) 0.30993(7) 0.39579(18) 0.0455(3) Uani 1 d . . .
C3 C 0.5762(2) 0.26840(6) 0.33283(17) 0.0413(3) Uani 1 d . . .
C2 C 0.5266(2) 0.20678(6) 0.35409(17) 0.0401(3) Uani 1 d . . .
C31 C 0.7547(3) 0.28558(8) 0.2480(2) 0.0553(4) Uani 1 d . . .
C7 C 0.6195(2) 0.09959(6) 0.32545(18) 0.0436(3) Uani 1 d . . .
C8 C 0.6818(3) 0.06459(9) 0.1793(2) 0.0573(4) Uani 1 d . . .
C1' C 0.7341(2) 0.08249(6) 0.47394(17) 0.0423(3) Uani 1 d . . .
C6' C 0.9297(2) 0.09372(8) 0.4866(2) 0.0547(4) Uani 1 d . . .
C5' C 1.0314(3) 0.07824(10) 0.6234(3) 0.0676(5) Uani 1 d . . .
C4' C 0.9406(3) 0.05099(9) 0.7480(3) 0.0694(5) Uani 1 d . . .
C3' C 0.7486(3) 0.03865(9) 0.7364(2) 0.0640(5) Uani 1 d . . .
C2' C 0.6452(3) 0.05507(7) 0.60078(19) 0.0509(4) Uani 1 d . . .
H6 H 0.145(3) 0.2173(8) 0.550(2) 0.059(5) Uiso 1 d . . .
H4 H 0.486(2) 0.3515(9) 0.383(2) 0.060(5) Uiso 1 d . . .
H311 H 0.776(3) 0.3285(12) 0.246(3) 0.092(7) Uiso 1 d . . .
H312 H 0.754(3) 0.2701(9) 0.136(3) 0.075(6) Uiso 1 d . . .
H313 H 0.870(3) 0.2689(9) 0.301(2) 0.073(6) Uiso 1 d . . .
H2 H 0.743(3) 0.1744(8) 0.247(2) 0.057(5) Uiso 1 d . . .
H7 H 0.484(2) 0.0916(7) 0.3412(19) 0.048(4) Uiso 1 d . . .
H81 H 0.599(3) 0.0752(10) 0.088(3) 0.090(7) Uiso 1 d . . .
H82 H 0.813(3) 0.0754(8) 0.153(2) 0.064(5) Uiso 1 d . . .
H83 H 0.672(3) 0.0197(10) 0.197(2) 0.077(6) Uiso 1 d . . .
H61' H 0.993(3) 0.1118(8) 0.403(2) 0.063(5) Uiso 1 d . . .
H51' H 1.162(3) 0.0884(10) 0.626(3) 0.085(7) Uiso 1 d . . .
H41' H 1.010(3) 0.0400(11) 0.846(3) 0.094(7) Uiso 1 d . . .
H31' H 0.680(3) 0.0197(9) 0.822(2) 0.070(6) Uiso 1 d . . .
H21' H 0.509(3) 0.0473(8) 0.595(2) 0.060(5) Uiso 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
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'
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
O1 N5 O2 122.54(15) . . ?
O1 N5 C5 118.82(15) . . ?
O2 N5 C5 118.63(15) . . ?
C2 N1 C6 117.70(13) . . ?
C2 N2 C7 124.61(13) . . ?
N1 C6 C5 122.72(15) . . ?
C6 C5 C4 119.75(14) . . ?
C6 C5 N5 119.83(14) . . ?
C4 C5 N5 120.39(14) . . ?
C3 C4 C5 119.63(14) . . ?
C2 C3 C4 117.01(13) . . ?
C4 C3 C31 122.22(14) . . ?
C2 C3 C31 120.76(14) . . ?
N1 C2 N2 117.25(13) . . ?
N2 C2 C3 119.56(13) . . ?
N1 C2 C3 123.19(13) . . ?
N2 C7 C1' 110.82(12) . . ?
N2 C7 C8 108.66(13) . . ?
C1' C7 C8 112.20(13) . . ?
C2' C1' C6' 118.38(16) . . ?
C2' C1' C7 120.42(14) . . ?
C6' C1' C7 121.20(14) . . ?
C5' C6' C1' 120.36(17) . . ?
C4' C5' C6' 120.39(19) . . ?
C3' C4' C5' 119.99(19) . . ?
C4' C3' C2' 119.86(19) . . ?
C3' C2' C1' 120.99(17) . . ?
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 1.226(2) . ?
O2 N5 1.228(2) . ?
N5 C5 1.441(2) . ?
N1 C6 1.332(2) . ?
N1 C2 1.3470(18) . ?
N2 C2 1.3469(19) . ?
N2 C7 1.4685(18) . ?
C6 C5 1.378(2) . ?
C5 C4 1.392(2) . ?
C4 C3 1.363(2) . ?
C3 C2 1.431(2) . ?
C3 C31 1.497(2) . ?
C7 C1' 1.515(2) . ?
C7 C8 1.524(2) . ?
C1' C2' 1.385(2) . ?
C1' C6' 1.390(2) . ?
C6' C5' 1.381(3) . ?
C5' C4' 1.375(3) . ?
C4' C3' 1.370(3) . ?
C3' C2' 1.384(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10123190
