#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:13:40 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180066 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/12/7051213.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_7051213
loop_
_publ_author_name
'Olivier Maury'
'Jean-Paul Guégan'
'Thierry Renouard'
'Adam Hilton'
'Philippe Dupau'
'Nicolas Sandon'
'Loïc Toupet'
'Hubert Le Bozec'
_publ_section_title
;
 Design and synthesis of 4,4'-π-conjugated[2,2']-bipyridines: a
 versatile class of tunable chromophores and fluorophores
;
_journal_issue                   12
_journal_name_full               'New J. Chem.'
_journal_page_first              1553
_journal_page_last               1566
_journal_paper_doi               10.1039/b106096c
_journal_volume                  25
_journal_year                    2001
_chemical_formula_sum            'C16 H18 N3'
_chemical_formula_weight         252.33
_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                 92.13(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.309(3)
_cell_length_b                   7.698(5)
_cell_length_c                   25.101(7)
_cell_measurement_temperature    293(2)
_cell_volume                     1411.3(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0616
_diffrn_reflns_av_sigmaI/netI    0.1439
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            3264
_diffrn_reflns_theta_full        26.96
_diffrn_reflns_theta_max         26.96
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.072
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0007(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.896
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.896
_refine_ls_R_factor_all          0.2724
_refine_ls_R_factor_gt           0.0633
_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)+(0.0821P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1429
_refine_ls_wR_factor_ref         0.2056
_reflns_number_gt                872
_reflns_number_total             3035
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b106096c.txt
_cod_data_source_block           compound_8
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7051213
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2672(5) 0.0634(5) 0.98447(12) 0.0874(11) Uani 1 1 d . . .
N8 N 0.6453(5) 0.0455(4) 0.82162(11) 0.0739(9) Uani 1 1 d . . .
N15 N 0.9763(5) 0.0493(5) 0.62386(14) 0.0964(11) Uani 1 1 d . . .
C2 C 0.4436(5) 0.0267(5) 0.97628(12) 0.0685(11) Uani 1 1 d . . .
C3 C 0.5184(5) 0.0371(5) 0.92661(13) 0.0704(11) Uani 1 1 d . . .
H3 H 0.6413 0.0107 0.9226 0.084 Uiso 1 1 calc R . .
C4 C 0.4104(6) 0.0867(5) 0.88292(14) 0.0711(11) Uani 1 1 d . . .
C5 C 0.2293(6) 0.1250(5) 0.89186(15) 0.0845(13) Uani 1 1 d . . .
H5 H 0.1515 0.1604 0.8638 0.101 Uiso 1 1 calc R . .
C6 C 0.1648(6) 0.1105(6) 0.94240(18) 0.1013(15) Uani 1 1 d . . .
H6 H 0.0420 0.1353 0.9473 0.122 Uiso 1 1 calc R . .
C7 C 0.4838(7) 0.0965(5) 0.82947(14) 0.0761(12) Uani 1 1 d . . .
H7 H 0.4117 0.1403 0.8013 0.091 Uiso 1 1 calc R . .
C9 C 0.7195(5) 0.0553(5) 0.77048(14) 0.0659(10) Uani 1 1 d . . .
C10 C 0.8741(6) -0.0447(5) 0.76292(15) 0.0774(11) Uani 1 1 d . . .
H10 H 0.9209 -0.1121 0.7910 0.093 Uiso 1 1 calc R . .
C11 C 0.9599(5) -0.0474(5) 0.71557(15) 0.0789(12) Uani 1 1 d . . .
H11 H 1.0636 -0.1158 0.7121 0.095 Uiso 1 1 calc R . .
C12 C 0.8945(5) 0.0509(5) 0.67219(15) 0.0720(11) Uani 1 1 d . . .
C13 C 0.7421(5) 0.1533(5) 0.68049(14) 0.0767(12) Uani 1 1 d . . .
H13 H 0.6968 0.2233 0.6528 0.092 Uiso 1 1 calc R . .
C14 C 0.6561(5) 0.1549(5) 0.72804(14) 0.0718(11) Uani 1 1 d . . .
H14 H 0.5532 0.2243 0.7318 0.086 Uiso 1 1 calc R . .
C16 C 1.1429(6) -0.0538(6) 0.61490(17) 0.1022(14) Uani 1 1 d . . .
H16A H 1.1366 -0.1624 0.6343 0.123 Uiso 1 1 calc R . .
H16B H 1.1488 -0.0810 0.5773 0.123 Uiso 1 1 calc R . .
C17 C 1.3082(6) 0.0400(7) 0.6322(2) 0.165(2) Uani 1 1 d . . .
H17A H 1.4136 -0.0310 0.6265 0.198 Uiso 1 1 calc R . .
H17B H 1.3026 0.0670 0.6695 0.198 Uiso 1 1 calc R . .
H17C H 1.3170 0.1456 0.6122 0.198 Uiso 1 1 calc R . .
C18 C 0.9200(8) 0.1656(7) 0.58070(19) 0.126(2) Uani 1 1 d . . .
H18A H 1.0256 0.1934 0.5600 0.151 Uiso 1 1 calc R . .
H18B H 0.8752 0.2729 0.5957 0.151 Uiso 1 1 calc R . .
C19 C 0.7745(8) 0.0898(8) 0.54465(19) 0.156(3) Uani 1 1 d . . .
H19A H 0.7417 0.1719 0.5171 0.187 Uiso 1 1 calc R . .
H19B H 0.6689 0.0634 0.5648 0.187 Uiso 1 1 calc R . .
H19C H 0.8193 -0.0147 0.5288 0.187 Uiso 1 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'
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 117.0(3) . . ?
C7 N8 C9 121.0(3) . . ?
C12 N15 C18 122.2(4) . . ?
C12 N15 C16 121.9(4) . . ?
C18 N15 C16 115.4(3) . . ?
N1 C2 C3 122.7(3) . . ?
N1 C2 C2 116.4(4) . 3_657 ?
C3 C2 C2 120.9(5) . 3_657 ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 116.9(4) . . ?
C3 C4 C7 121.6(4) . . ?
C5 C4 C7 121.5(4) . . ?
C6 C5 C4 119.8(4) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
N1 C6 C5 123.8(4) . . ?
N1 C6 H6 118.1 . . ?
C5 C6 H6 118.1 . . ?
N8 C7 C4 120.1(4) . . ?
N8 C7 H7 120.0 . . ?
C4 C7 H7 120.0 . . ?
C14 C9 C10 117.1(3) . . ?
C14 C9 N8 127.0(4) . . ?
C10 C9 N8 115.9(4) . . ?
C11 C10 C9 122.0(4) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C10 C11 C12 121.1(4) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
N15 C12 C13 121.1(4) . . ?
N15 C12 C11 122.5(4) . . ?
C13 C12 C11 116.4(3) . . ?
C14 C13 C12 122.2(4) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C13 C14 C9 121.1(4) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
C17 C16 N15 111.5(4) . . ?
C17 C16 H16A 109.3 . . ?
N15 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
N15 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N15 C18 C19 112.8(5) . . ?
N15 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
N15 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
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
N1 C6 1.322(5) . ?
N1 C2 1.343(4) . ?
N8 C7 1.267(4) . ?
N8 C9 1.414(4) . ?
N15 C12 1.373(4) . ?
N15 C18 1.453(5) . ?
N15 C16 1.478(5) . ?
C2 C3 1.382(4) . ?
C2 C2 1.482(7) 3_657 ?
C3 C4 1.381(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(5) . ?
C4 C7 1.465(5) . ?
C5 C6 1.374(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C9 C14 1.378(4) . ?
C9 C10 1.386(5) . ?
C10 C11 1.364(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.395(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(5) . ?
C13 C14 1.370(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C16 C17 1.459(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.489(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 0.2(6) . . . . ?
C6 N1 C2 C2 -179.7(4) . . . 3_657 ?
N1 C2 C3 C4 -0.1(6) . . . . ?
C2 C2 C3 C4 179.8(4) 3_657 . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C2 C3 C4 C7 -179.0(3) . . . . ?
C3 C4 C5 C6 -0.8(6) . . . . ?
C7 C4 C5 C6 178.6(4) . . . . ?
C2 N1 C6 C5 -0.6(7) . . . . ?
C4 C5 C6 N1 1.0(7) . . . . ?
C9 N8 C7 C4 -179.4(3) . . . . ?
C3 C4 C7 N8 5.8(6) . . . . ?
C5 C4 C7 N8 -173.5(4) . . . . ?
C7 N8 C9 C14 17.8(6) . . . . ?
C7 N8 C9 C10 -163.2(4) . . . . ?
C14 C9 C10 C11 -0.8(6) . . . . ?
N8 C9 C10 C11 -179.9(4) . . . . ?
C9 C10 C11 C12 -0.3(6) . . . . ?
C18 N15 C12 C13 6.0(6) . . . . ?
C16 N15 C12 C13 177.6(4) . . . . ?
C18 N15 C12 C11 -173.2(4) . . . . ?
C16 N15 C12 C11 -1.6(6) . . . . ?
C10 C11 C12 N15 -179.2(4) . . . . ?
C10 C11 C12 C13 1.6(6) . . . . ?
N15 C12 C13 C14 178.8(4) . . . . ?
C11 C12 C13 C14 -1.9(6) . . . . ?
C12 C13 C14 C9 0.9(6) . . . . ?
C10 C9 C14 C13 0.5(5) . . . . ?
N8 C9 C14 C13 179.5(3) . . . . ?
C12 N15 C16 C17 -84.3(5) . . . . ?
C18 N15 C16 C17 87.9(5) . . . . ?
C12 N15 C18 C19 -90.7(5) . . . . ?
C16 N15 C18 C19 97.2(5) . . . . ?
