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#$Date: 2016-03-26 16:22:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180335 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/04/7200452.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_7200452
loop_
_publ_author_name
'Aliev, Abil E.'
'Moïse, Joëlle'
'Motherwell, William B.'
'Nič, Miloslav'
'Courtier-Murias, Denis'
'Tocher, Derek A.'
_publ_section_title
;
 Probing weak non-covalent interactions in solution and solid states
 with designed molecules
;
_journal_issue                   1
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_page_first              97
_journal_page_last               100
_journal_paper_doi               10.1039/b815906h
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C18 H16 N2'
_chemical_formula_weight         260.33
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_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                 100.271(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8169(18)
_cell_length_b                   11.8799(15)
_cell_length_c                   8.5789(11)
_cell_measurement_temperature    293(2)
_cell_volume                     1385.6(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.959
_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  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12052
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.50
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9934
_exptl_absorpt_correction_T_min  0.9753
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0594
_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)+(0.0685P)²+0.2468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1536
_reflns_number_gt                2412
_reflns_number_total             3318
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b815906h.txt
_cod_data_source_block           str0215
_cod_database_code               7200452
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 0.31821(17) 0.3225(2) 0.5809(3) 0.0728(6) Uani 1 1 d . . .
H1N H 0.326(2) 0.253(3) 0.542(4) 0.114(12) Uiso 1 1 d . . .
H2N H 0.375(2) 0.344(2) 0.649(3) 0.087(9) Uiso 1 1 d . . .
N2 N 0.45773(12) 0.37057(15) 0.3058(2) 0.0629(5) Uani 1 1 d . . .
C1 C 0.30283(12) 0.59834(14) 0.2434(2) 0.0411(4) Uani 1 1 d . . .
C2 C 0.38276(14) 0.65311(16) 0.2014(2) 0.0494(5) Uani 1 1 d . . .
H2A H 0.4159 0.7080 0.2676 0.059 Uiso 1 1 calc R . .
C3 C 0.41334(16) 0.62624(18) 0.0611(2) 0.0585(5) Uani 1 1 d . . .
H3A H 0.4681 0.6616 0.0343 0.070 Uiso 1 1 calc R . .
C4 C 0.36305(16) 0.5477(2) -0.0382(2) 0.0621(6) Uani 1 1 d . . .
H4A H 0.3835 0.5305 -0.1330 0.075 Uiso 1 1 calc R . .
C5 C 0.28187(15) 0.49364(18) 0.0011(2) 0.0552(5) Uani 1 1 d . . .
H5A H 0.2475 0.4412 -0.0681 0.066 Uiso 1 1 calc R . .
C6 C 0.25163(12) 0.51748(15) 0.14342(19) 0.0425(4) Uani 1 1 d . . .
C7 C 0.26875(12) 0.61729(15) 0.3991(2) 0.0440(4) Uani 1 1 d . . .
H7A H 0.2957 0.6888 0.4445 0.053 Uiso 1 1 calc R . .
C8 C 0.15785(13) 0.62316(15) 0.3723(2) 0.0455(4) Uani 1 1 d . . .
C9 C 0.10652(16) 0.70077(17) 0.4470(3) 0.0608(5) Uani 1 1 d . . .
H9A H 0.1403 0.7557 0.5125 0.073 Uiso 1 1 calc R . .
C10 C 0.00491(17) 0.6961(2) 0.4237(3) 0.0709(6) Uani 1 1 d . . .
H10A H -0.0295 0.7479 0.4742 0.085 Uiso 1 1 calc R . .
C11 C -0.04540(16) 0.6161(2) 0.3269(3) 0.0702(7) Uani 1 1 d . . .
H11A H -0.1137 0.6135 0.3121 0.084 Uiso 1 1 calc R . .
C12 C 0.00530(14) 0.53908(19) 0.2513(3) 0.0610(5) Uani 1 1 d . . .
H12A H -0.0290 0.4850 0.1850 0.073 Uiso 1 1 calc R . .
C13 C 0.10726(13) 0.54221(15) 0.2738(2) 0.0459(4) Uani 1 1 d . . .
C14 C 0.16940(12) 0.45725(15) 0.2042(2) 0.0458(4) Uani 1 1 d . . .
H14A H 0.1280 0.4187 0.1155 0.055 Uiso 1 1 calc R . .
C15 C 0.21067(13) 0.36917(15) 0.3318(2) 0.0481(4) Uani 1 1 d . . .
H15A H 0.1601 0.3528 0.3938 0.058 Uiso 1 1 calc R . .
H15B H 0.2235 0.3002 0.2785 0.058 Uiso 1 1 calc R . .
C16 C 0.30533(13) 0.40244(16) 0.4467(2) 0.0466(4) Uani 1 1 d . . .
C17 C 0.30562(13) 0.52145(16) 0.5161(2) 0.0475(4) Uani 1 1 d . . .
H17A H 0.3723 0.5391 0.5672 0.057 Uiso 1 1 calc R . .
H17B H 0.2653 0.5208 0.5979 0.057 Uiso 1 1 calc R . .
C18 C 0.39068(13) 0.38916(15) 0.3624(2) 0.0476(4) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.31(16) . . ?
C2 C1 C7 123.33(16) . . ?
C6 C1 C7 116.31(15) . . ?
C3 C2 C1 120.02(19) . . ?
C4 C3 C2 120.00(19) . . ?
C3 C4 C5 120.59(18) . . ?
C4 C5 C6 120.19(19) . . ?
C5 C6 C1 118.86(17) . . ?
C5 C6 C14 124.70(17) . . ?
C1 C6 C14 116.36(14) . . ?
C8 C7 C1 109.87(14) . . ?
C8 C7 C17 109.98(14) . . ?
C1 C7 C17 110.28(14) . . ?
C13 C8 C9 119.96(18) . . ?
C13 C8 C7 116.69(15) . . ?
C9 C8 C7 123.26(17) . . ?
C10 C9 C8 119.7(2) . . ?
C11 C10 C9 120.6(2) . . ?
C10 C11 C12 120.0(2) . . ?
C11 C12 C13 120.2(2) . . ?
C8 C13 C12 119.56(18) . . ?
C8 C13 C14 116.32(15) . . ?
C12 C13 C14 124.03(17) . . ?
C6 C14 C13 109.52(15) . . ?
C6 C14 C15 111.05(14) . . ?
C13 C14 C15 109.54(15) . . ?
C16 C15 C14 116.25(14) . . ?
N1 C16 C18 108.22(15) . . ?
N1 C16 C17 107.36(17) . . ?
C18 C16 C17 109.69(15) . . ?
N1 C16 C15 107.68(16) . . ?
C18 C16 C15 108.36(15) . . ?
C17 C16 C15 115.31(15) . . ?
C16 C17 C7 116.74(14) . . ?
N2 C18 C16 173.91(19) . . ?
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 C16 1.478(2) . ?
N2 C18 1.141(2) . ?
C1 C2 1.384(2) . ?
C1 C6 1.394(2) . ?
C1 C7 1.510(2) . ?
C2 C3 1.382(3) . ?
C3 C4 1.366(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.388(2) . ?
C6 C14 1.512(3) . ?
C7 C8 1.510(2) . ?
C7 C17 1.543(3) . ?
C8 C13 1.384(3) . ?
C8 C9 1.388(3) . ?
C9 C10 1.383(3) . ?
C10 C11 1.367(3) . ?
C11 C12 1.383(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.515(2) . ?
C14 C15 1.548(3) . ?
C15 C16 1.542(3) . ?
C16 C18 1.498(3) . ?
C16 C17 1.534(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
_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 C1 C2 C3 -1.2(3) . . . . ?
C7 C1 C2 C3 175.95(17) . . . . ?
C1 C2 C3 C4 1.7(3) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C4 C5 C6 C1 1.5(3) . . . . ?
C4 C5 C6 C14 -174.95(18) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
C7 C1 C6 C5 -177.77(16) . . . . ?
C2 C1 C6 C14 176.35(16) . . . . ?
C7 C1 C6 C14 -1.0(2) . . . . ?
C2 C1 C7 C8 138.35(17) . . . . ?
C6 C1 C7 C8 -44.4(2) . . . . ?
C2 C1 C7 C17 -100.27(19) . . . . ?
C6 C1 C7 C17 76.99(18) . . . . ?
C1 C7 C8 C13 45.1(2) . . . . ?
C17 C7 C8 C13 -76.43(19) . . . . ?
C1 C7 C8 C9 -138.26(18) . . . . ?
C17 C7 C8 C9 100.2(2) . . . . ?
C13 C8 C9 C10 0.5(3) . . . . ?
C7 C8 C9 C10 -175.95(19) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C9 C8 C13 C12 -0.3(3) . . . . ?
C7 C8 C13 C12 176.44(17) . . . . ?
C9 C8 C13 C14 -176.87(17) . . . . ?
C7 C8 C13 C14 -0.2(2) . . . . ?
C11 C12 C13 C8 -0.2(3) . . . . ?
C11 C12 C13 C14 176.12(19) . . . . ?
C5 C6 C14 C13 -137.68(18) . . . . ?
C1 C6 C14 C13 45.8(2) . . . . ?
C5 C6 C14 C15 101.2(2) . . . . ?
C1 C6 C14 C15 -75.35(19) . . . . ?
C8 C13 C14 C6 -45.2(2) . . . . ?
C12 C13 C14 C6 138.39(19) . . . . ?
C8 C13 C14 C15 76.83(19) . . . . ?
C12 C13 C14 C15 -99.6(2) . . . . ?
C6 C14 C15 C16 37.6(2) . . . . ?
C13 C14 C15 C16 -83.53(18) . . . . ?
C14 C15 C16 N1 165.88(16) . . . . ?
C14 C15 C16 C18 -77.28(19) . . . . ?
C14 C15 C16 C17 46.1(2) . . . . ?
N1 C16 C17 C7 -165.77(15) . . . . ?
C18 C16 C17 C7 76.85(19) . . . . ?
C15 C16 C17 C7 -45.8(2) . . . . ?
C8 C7 C17 C16 82.97(18) . . . . ?
C1 C7 C17 C16 -38.3(2) . . . . ?
N1 C16 C18 N2 12(2) . . . . ?
C17 C16 C18 N2 128.5(19) . . . . ?
C15 C16 C18 N2 -104.9(19) . . . . ?
