#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/68/1506819.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_1506819
loop_
_publ_author_name
'Nesterov, Volodymyr V.'
'Antipin, Mikhail Yu.'
'Nesterov, Vladimir N.'
'Moore, Craig E.'
'Cardelino, Beatriz H.'
'Timofeeva, Tatiana V.'
_publ_section_title
;
 Thermally Stable Heterocyclic Imines as New Potential Nonlinear Optical
 Materials†
;
_journal_issue                   25
_journal_name_full               'The Journal of Physical Chemistry B'
_journal_page_first              8531
_journal_paper_doi               10.1021/jp0367528
_journal_volume                  108
_journal_year                    2004
_chemical_formula_moiety         'C13 H9 N5'
_chemical_formula_sum            'C13 H9 N5'
_chemical_formula_weight         235.25
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.208(2)
_cell_length_b                   22.983(5)
_cell_length_c                   5.0410(10)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      11
_cell_volume                     1182.7(4)
_computing_cell_refinement       'Enraf-Nonius CAD4'
_computing_data_collection       'Enraf-Nonius CAD4 (Enraf-Nonius, 1989)'
_computing_data_reduction        'Siemens SHELXTL (Sheldrick, 1994)'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       θ/2θ
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1881
_diffrn_reflns_theta_full        29.97
_diffrn_reflns_theta_max         29.97
_diffrn_reflns_theta_min         1.77
_diffrn_standards_decay_%        3
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   4(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1881
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0419
_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/[σ²(Fo²)+(0.0639P)²+0.0553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                1250
_reflns_number_total             1881
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jp0367528si20030915_041846.cif
_cod_data_source_block           7d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_database_code               1506819
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.69554(18) 0.37165(8) -0.0780(5) 0.0408(5) Uani 1 1 d .
N2 N 0.8132(3) 0.25563(10) 0.2964(7) 0.0668(8) Uani 1 1 d .
N3 N 0.5469(2) 0.17433(9) -0.1587(7) 0.0659(8) Uani 1 1 d .
N4 N 0.5128(3) 0.31258(9) -0.3839(6) 0.0628(7) Uani 1 1 d .
H4A H 0.5222 0.3494 -0.4076 0.075 Uiso 1 1 calc R
H4B H 0.4564 0.2935 -0.4763 0.075 Uiso 1 1 calc R
N5 N 0.8753(2) 0.54698(8) 0.1853(5) 0.0443(5) Uani 1 1 d .
H5A H 0.9189 0.5732 0.2694 0.053 Uiso 1 1 calc R
C1 C 0.8800(2) 0.48926(10) 0.2349(6) 0.0444(6) Uani 1 1 d .
H1A H 0.9305 0.4719 0.3665 0.053 Uiso 1 1 calc R
C2 C 0.7992(2) 0.45989(9) 0.0618(5) 0.0395(5) Uani 1 1 d .
C3 C 0.7398(2) 0.50339(9) -0.1077(5) 0.0359(5) Uani 1 1 d .
C4 C 0.6504(2) 0.50284(10) -0.3156(6) 0.0433(6) Uani 1 1 d .
H4C H 0.6169 0.4679 -0.3787 0.052 Uiso 1 1 calc R
C5 C 0.6120(3) 0.55505(11) -0.4272(7) 0.0520(7) Uani 1 1 d .
H5B H 0.5509 0.5550 -0.5640 0.062 Uiso 1 1 calc R
C6 C 0.6634(3) 0.60786(10) -0.3384(7) 0.0543(7) Uani 1 1 d .
H6A H 0.6363 0.6424 -0.4179 0.065 Uiso 1 1 calc R
C7 C 0.7530(3) 0.60976(10) -0.1360(7) 0.0488(6) Uani 1 1 d .
H7A H 0.7879 0.6449 -0.0781 0.059 Uiso 1 1 calc R
C8 C 0.7899(2) 0.55744(9) -0.0204(5) 0.0380(5) Uani 1 1 d .
C9 C 0.7774(2) 0.39823(9) 0.0733(6) 0.0419(6) Uani 1 1 d .
H9A H 0.8248 0.3765 0.1959 0.050 Uiso 1 1 calc R
C10 C 0.6774(2) 0.31168(9) -0.0479(6) 0.0396(5) Uani 1 1 d .
C11 C 0.7508(3) 0.27887(9) 0.1418(7) 0.0458(7) Uani 1 1 d .
C12 C 0.5860(3) 0.28480(9) -0.2025(6) 0.0432(6) Uani 1 1 d .
C13 C 0.5646(3) 0.22291(10) -0.1743(7) 0.0490(7) Uani 1 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 N1 C10 119.3(2)
C12 N4 H4A 120.0
C12 N4 H4B 120.0
H4A N4 H4B 120.0
C1 N5 C8 109.5(2)
C1 N5 H5A 125.3
C8 N5 H5A 125.3
N5 C1 C2 110.0(2)
N5 C1 H1A 125.0
C2 C1 H1A 125.0
C1 C2 C9 123.4(2)
C1 C2 C3 106.6(2)
C9 C2 C3 129.8(2)
C4 C3 C8 118.7(2)
C4 C3 C2 135.5(2)
C8 C3 C2 105.7(2)
C5 C4 C3 119.0(2)
C5 C4 H4C 120.5
C3 C4 H4C 120.5
C4 C5 C6 121.2(3)
C4 C5 H5B 119.4
C6 C5 H5B 119.4
C7 C6 C5 121.1(2)
C7 C6 H6A 119.4
C5 C6 H6A 119.4
C6 C7 C8 117.8(2)
C6 C7 H7A 121.1
C8 C7 H7A 121.1
N5 C8 C7 129.8(2)
N5 C8 C3 108.1(2)
C7 C8 C3 122.2(2)
N1 C9 C2 123.1(2)
N1 C9 H9A 118.5
C2 C9 H9A 118.5
C12 C10 N1 118.4(2)
C12 C10 C11 120.1(2)
N1 C10 C11 121.5(2)
N2 C11 C10 176.0(3)
N4 C12 C10 123.7(2)
N4 C12 C13 116.8(2)
C10 C12 C13 119.5(3)
N3 C13 C12 178.3(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C9 1.286(3)
N1 C10 1.399(3)
N2 C11 1.139(4)
N3 C13 1.134(3)
N4 C12 1.343(4)
N4 H4A 0.8600
N4 H4B 0.8600
N5 C1 1.351(3)
N5 C8 1.375(3)
N5 H5A 0.8600
C1 C2 1.377(4)
C1 H1A 0.9300
C2 C9 1.436(3)
C2 C3 1.448(3)
C3 C4 1.390(4)
C3 C8 1.414(3)
C4 C5 1.382(4)
C4 H4C 0.9300
C5 C6 1.396(4)
C5 H5B 0.9300
C6 C7 1.372(4)
C6 H6A 0.9300
C7 C8 1.388(3)
C7 H7A 0.9300
C9 H9A 0.9300
C10 C12 1.364(4)
C10 C11 1.430(4)
C12 C13 1.446(3)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C8 N5 C1 C2 0.6(3)
N5 C1 C2 C9 -176.5(2)
N5 C1 C2 C3 -0.1(3)
C1 C2 C3 C4 -179.2(3)
C9 C2 C3 C4 -3.1(5)
C1 C2 C3 C8 -0.4(3)
C9 C2 C3 C8 175.6(2)
C8 C3 C4 C5 -1.0(4)
C2 C3 C4 C5 177.7(3)
C3 C4 C5 C6 1.3(4)
C4 C5 C6 C7 -0.5(5)
C5 C6 C7 C8 -0.7(5)
C1 N5 C8 C7 179.1(3)
C1 N5 C8 C3 -0.9(3)
C6 C7 C8 N5 -179.0(3)
C6 C7 C8 C3 1.0(4)
C4 C3 C8 N5 179.8(2)
C2 C3 C8 N5 0.8(3)
C4 C3 C8 C7 -0.2(4)
C2 C3 C8 C7 -179.2(3)
C10 N1 C9 C2 -178.0(2)
C1 C2 C9 N1 175.4(2)
C3 C2 C9 N1 0.0(4)
C9 N1 C10 C12 177.2(2)
C9 N1 C10 C11 -1.9(4)
C12 C10 C11 N2 177(5)
N1 C10 C11 N2 -4(5)
N1 C10 C12 N4 0.5(4)
C11 C10 C12 N4 179.6(3)
N1 C10 C12 C13 -179.5(2)
C11 C10 C12 C13 -0.4(4)
N4 C12 C13 N3 29(10)
C10 C12 C13 N3 -151(10)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 30651762 ChemSpider
