#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/39/2223911.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2223911
loop_
_publ_author_name
'Lee, Cho Hee'
'Kim, Mi Jong'
'Kim, Yeong-Joon'
'Je, Jong Tae'
'Lee, You-Soon'
'Kang, Sung Kwon'
_publ_section_title
;
 anti-9,10-Di(1-naphthyl)anthracene pyridine disolvate
;
_journal_coeditor_code           LH2928
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2842
_journal_paper_doi               10.1107/S1600536809042706
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C34 H22, 2C5 H5 N'
_chemical_formula_moiety         'C34 H22, 2(C5 H5 N)'
_chemical_formula_sum            'C44 H32 N2'
_chemical_formula_weight         588.72
_chemical_name_systematic
;
anti-9,10-Di(1-naphthyl)anthracene pyridine disolvate
;
_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'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 93.34(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.9810(18)
_cell_length_b                   24.166(5)
_cell_length_c                   7.2740(15)
_cell_measurement_reflns_used    5150
_cell_measurement_temperature    174(2)
_cell_measurement_theta_max      28.1
_cell_measurement_theta_min      2.27
_cell_volume                     1576.0(6)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      174(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16543
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.216
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0481P)²+0.4153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1155
_reflns_number_gt                3121
_reflns_number_total             3897
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2928.cif
_cod_data_source_block           I
_cod_database_code               2223911
_cod_database_fobs_code          2223911
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.05625(11) 0.54185(4) 0.38731(15) 0.0273(2) Uani d . 1 . .
C C2 0.11828(13) 0.58393(5) 0.27710(17) 0.0338(3) Uani d . 1 . .
H H2 0.0574 0.6018 0.188 0.041 Uiso calc R 1 . .
C C3 0.26455(14) 0.59831(5) 0.29986(19) 0.0396(3) Uani d . 1 . .
H H3 0.3027 0.6256 0.2256 0.048 Uiso calc R 1 . .
C C4 0.35912(13) 0.57214(5) 0.43571(19) 0.0389(3) Uani d . 1 . .
H H4 0.4591 0.5822 0.4496 0.047 Uiso calc R 1 . .
C C5 0.30516(12) 0.53240(5) 0.54615(17) 0.0324(3) Uani d . 1 . .
H H5 0.3687 0.5158 0.6353 0.039 Uiso calc R 1 . .
C C6 0.15163(11) 0.51567(4) 0.52738(15) 0.0268(2) Uani d . 1 . .
C C7 -0.09396(11) 0.52557(4) 0.36048(15) 0.0268(2) Uani d . 1 . .
C C8 -0.19254(12) 0.55196(5) 0.21282(15) 0.0294(2) Uani d . 1 . .
C C9 -0.26471(11) 0.60328(5) 0.24560(15) 0.0278(2) Uani d . 1 . .
C C10 -0.24646(12) 0.63180(5) 0.41558(17) 0.0326(3) Uani d . 1 . .
H H10 -0.1844 0.6171 0.51 0.039 Uiso calc R 1 . .
C C11 -0.31893(14) 0.68071(5) 0.4428(2) 0.0424(3) Uani d . 1 . .
H H11 -0.3059 0.6989 0.5553 0.051 Uiso calc R 1 . .
C C12 -0.41311(14) 0.70367(5) 0.3013(2) 0.0459(3) Uani d . 1 . .
H H12 -0.4615 0.737 0.3205 0.055 Uiso calc R 1 . .
C C13 -0.43357(13) 0.67737(5) 0.1369(2) 0.0419(3) Uani d . 1 . .
H H13 -0.4966 0.6929 0.0449 0.05 Uiso calc R 1 . .
C C14 -0.36078(12) 0.62677(5) 0.10307(17) 0.0333(3) Uani d . 1 . .
C C15 -0.38159(15) 0.59853(6) -0.06721(18) 0.0446(3) Uani d . 1 . .
H H15 -0.4441 0.6136 -0.1607 0.054 Uiso calc R 1 . .
C C16 -0.31118(16) 0.54967(7) -0.09547(18) 0.0491(4) Uani d . 1 . .
H H16 -0.3257 0.5316 -0.2079 0.059 Uiso calc R 1 . .
C C17 -0.21627(14) 0.52640(6) 0.04517(18) 0.0409(3) Uani d . 1 . .
H H17 -0.1687 0.493 0.0239 0.049 Uiso calc R 1 . .
N N18 0.26262(13) 0.69991(6) 0.82489(18) 0.0519(3) Uani d . 1 . .
C C19 0.19358(17) 0.74566(6) 0.8706(2) 0.0503(3) Uani d . 1 . .
H H19 0.25 0.7778 0.8841 0.06 Uiso calc R 1 . .
C C20 0.04512(18) 0.74902(8) 0.8994(2) 0.0598(4) Uani d . 1 . .
H H20 0.0026 0.7826 0.9302 0.072 Uiso calc R 1 . .
C C21 -0.03967(18) 0.70250(9) 0.8825(2) 0.0664(5) Uani d . 1 . .
H H21 -0.1409 0.7036 0.9029 0.08 Uiso calc R 1 . .
C C22 0.0270(2) 0.65402(8) 0.8348(2) 0.0649(5) Uani d . 1 . .
H H22 -0.0279 0.6215 0.8212 0.078 Uiso calc R 1 . .
C C23 0.1781(2) 0.65463(7) 0.8073(2) 0.0588(4) Uani d . 1 . .
H H23 0.2232 0.6217 0.7748 0.071 Uiso calc R 1 . .
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 0 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 C1 C2 . . 121.55(10) ?
C7 C1 C6 . . 120.10(10) ?
C2 C1 C6 . . 118.35(10) ?
C3 C2 C1 . . 121.30(11) ?
C3 C2 H2 . . 119.4 ?
C1 C2 H2 . . 119.4 ?
C2 C3 C4 . . 120.49(11) ?
C2 C3 H3 . . 119.8 ?
C4 C3 H3 . . 119.8 ?
C5 C4 C3 . . 120.57(11) ?
C5 C4 H4 . . 119.7 ?
C3 C4 H4 . . 119.7 ?
C4 C5 C6 . . 121.07(11) ?
C4 C5 H5 . . 119.5 ?
C6 C5 H5 . . 119.5 ?
C7 C6 C5 3_566 . 121.91(10) ?
C7 C6 C1 3_566 . 119.89(9) ?
C5 C6 C1 . . 118.19(10) ?
C6 C7 C1 3_566 . 120.01(10) ?
C6 C7 C8 3_566 . 119.79(9) ?
C1 C7 C8 . . 120.20(10) ?
C17 C8 C9 . . 119.43(11) ?
C17 C8 C7 . . 120.09(11) ?
C9 C8 C7 . . 120.47(10) ?
C10 C9 C8 . . 122.58(10) ?
C10 C9 C14 . . 118.34(11) ?
C8 C9 C14 . . 119.07(10) ?
C11 C10 C9 . . 120.96(11) ?
C11 C10 H10 . . 119.5 ?
C9 C10 H10 . . 119.5 ?
C10 C11 C12 . . 120.33(13) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C13 C12 C11 . . 120.29(12) ?
C13 C12 H12 . . 119.9 ?
C11 C12 H12 . . 119.9 ?
C12 C13 C14 . . 121.19(12) ?
C12 C13 H13 . . 119.4 ?
C14 C13 H13 . . 119.4 ?
C13 C14 C15 . . 121.98(12) ?
C13 C14 C9 . . 118.89(12) ?
C15 C14 C9 . . 119.13(12) ?
C16 C15 C14 . . 120.74(12) ?
C16 C15 H15 . . 119.6 ?
C14 C15 H15 . . 119.6 ?
C15 C16 C17 . . 120.21(12) ?
C15 C16 H16 . . 119.9 ?
C17 C16 H16 . . 119.9 ?
C8 C17 C16 . . 121.42(13) ?
C8 C17 H17 . . 119.3 ?
C16 C17 H17 . . 119.3 ?
C19 N18 C23 . . 116.01(14) ?
N18 C19 C20 . . 124.50(15) ?
N18 C19 H19 . . 117.8 ?
C20 C19 H19 . . 117.8 ?
C21 C20 C19 . . 118.96(16) ?
C21 C20 H20 . . 120.5 ?
C19 C20 H20 . . 120.5 ?
C20 C21 C22 . . 118.66(15) ?
C20 C21 H21 . . 120.7 ?
C22 C21 H21 . . 120.7 ?
C21 C22 C23 . . 118.33(16) ?
C21 C22 H22 . . 120.8 ?
C23 C22 H22 . . 120.8 ?
N18 C23 C22 . . 123.54(16) ?
N18 C23 H23 . . 118.2 ?
C22 C23 H23 . . 118.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C7 . 1.4079(15) ?
C1 C2 . 1.4281(16) ?
C1 C6 . 1.4388(16) ?
C2 C3 . 1.3596(17) ?
C2 H2 . 0.93 ?
C3 C4 . 1.4143(19) ?
C3 H3 . 0.93 ?
C4 C5 . 1.3593(17) ?
C4 H4 . 0.93 ?
C5 C6 . 1.4358(15) ?
C5 H5 . 0.93 ?
C6 C7 3_566 1.4057(15) ?
C7 C6 3_566 1.4057(15) ?
C7 C8 . 1.4944(16) ?
C8 C17 . 1.3725(17) ?
C8 C9 . 1.4260(15) ?
C9 C10 . 1.4166(16) ?
C9 C14 . 1.4273(16) ?
C10 C11 . 1.3693(17) ?
C10 H10 . 0.93 ?
C11 C12 . 1.408(2) ?
C11 H11 . 0.93 ?
C12 C13 . 1.357(2) ?
C12 H12 . 0.93 ?
C13 C14 . 1.4149(18) ?
C13 H13 . 0.93 ?
C14 C15 . 1.4170(19) ?
C15 C16 . 1.361(2) ?
C15 H15 . 0.93 ?
C16 C17 . 1.4099(19) ?
C16 H16 . 0.93 ?
C17 H17 . 0.93 ?
N18 C19 . 1.3197(19) ?
N18 C23 . 1.333(2) ?
C19 C20 . 1.364(2) ?
C19 H19 . 0.93 ?
C20 C21 . 1.359(3) ?
C20 H20 . 0.93 ?
C21 C22 . 1.370(3) ?
C21 H21 . 0.93 ?
C22 C23 . 1.383(3) ?
C22 H22 . 0.93 ?
C23 H23 . 0.93 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C13 H13 N18 1_454 0.93 2.62 3.4887(19) 156 yes
C4 H4 Cg1 1_655 0.93 2.86 3.6026(15) 138 yes
C16 H16 Cg2 3_565 0.93 2.85 3.6177(18) 141 yes
