#------------------------------------------------------------------------------
#$Date: 2021-05-12 07:39:35 +0300 (Wed, 12 May 2021) $
#$Revision: 265125 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/38/2243823.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_2243823
loop_
_publ_author_name
'Zhao, Meng'
'Zhang, Gang'
'Zhang, Jingmiao'
'Huang, Shan'
'Liu, Xiuxia'
'Li, Fei'
_publ_section_title
;
 Crystal structure of 4-(anthracen-9-yl)pyridine
;
_journal_coeditor_code           DX2036
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              605
_journal_page_last               608
_journal_paper_doi               10.1107/S2056989021004710
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C19 H13 N'
_chemical_formula_moiety         'C19 H13 N'
_chemical_formula_sum            'C19 H13 N'
_chemical_formula_weight         255.30
_chemical_name_systematic
;
4-(Anthracen-9-yl)pyridine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.476(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0777(4)
_cell_length_b                   20.9211(16)
_cell_length_c                   10.2574(7)
_cell_measurement_reflns_used    2979
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.310
_cell_measurement_theta_min      3.723
_cell_volume                     1273.45(16)
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4703
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.336
_diffrn_reflns_theta_min         3.723
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       bulk
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.139
_refine_ls_extinction_coef       0.154(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0556P)²+0.3319P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                1022
_reflns_number_total             1144
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dx2036sup1.cif
_cod_data_source_block           I
_cod_database_code               2243823
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.699
_shelx_estimated_absorpt_t_max   0.745
loop_
_space_group_symop_operation_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'
'-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_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.000000 0.36240(5) 0.250000 0.0360(4) Uani d 1 . .
C C1 0.12815(18) 0.39626(5) 0.18480(11) 0.0359(3) Uani d 1 . .
H H1 0.219495 0.374032 0.138423 0.043 Uiso calc 1 . .
C C2 0.13369(17) 0.46237(5) 0.18183(10) 0.0324(3) Uani d 1 . .
H H2 0.226472 0.483317 0.134422 0.039 Uiso calc 1 . .
C C3 0.000000 0.49724(7) 0.250000 0.0266(4) Uani d 1 . .
C C4 0.000000 0.56870(6) 0.250000 0.0267(4) Uani d 1 . .
C C5 0.18833(15) 0.60220(5) 0.32231(9) 0.0279(3) Uani d 1 . .
C C6 0.38307(17) 0.57083(5) 0.39762(10) 0.0308(3) Uani d 1 . .
H H6 0.387809 0.526405 0.399226 0.037 Uiso calc 1 . .
C C7 0.56176(18) 0.60434(5) 0.46706(11) 0.0357(3) Uani d 1 . .
H H7 0.686262 0.582594 0.515636 0.043 Uiso calc 1 . .
C C8 0.56061(19) 0.67201(5) 0.46633(12) 0.0405(3) Uani d 1 . .
H H8 0.683709 0.694491 0.514440 0.049 Uiso calc 1 . .
C C9 0.38025(19) 0.70397(5) 0.39555(11) 0.0407(4) Uani d 1 . .
H H9 0.381857 0.748415 0.394805 0.049 Uiso calc 1 . .
C C10 0.18747(17) 0.67085(5) 0.32198(10) 0.0325(3) Uani d 1 . .
C C11 0.000000 0.70319(7) 0.250000 0.0371(4) Uani d 1 . .
H H11 0.000002 0.747643 0.250003 0.045 Uiso calc 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 0.0000 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C1 . 2 115.86(12) ?
N1 C1 H1 . . 117.9 ?
N1 C1 C2 . . 124.14(10) ?
C2 C1 H1 . . 117.9 ?
C1 C2 H2 . . 120.2 ?
C1 C2 C3 . . 119.63(10) ?
C3 C2 H2 . . 120.2 ?
C2 C3 C2 2 . 116.60(13) ?
C2 C3 C4 . . 121.70(6) ?
C2 C3 C4 2 . 121.70(6) ?
C5 C4 C3 2 . 119.84(6) ?
C5 C4 C3 . . 119.83(6) ?
C5 C4 C5 . 2 120.33(13) ?
C4 C5 C6 . . 122.77(10) ?
C4 C5 C10 . . 119.61(9) ?
C6 C5 C10 . . 117.62(9) ?
C5 C6 H6 . . 119.2 ?
C7 C6 C5 . . 121.52(10) ?
C7 C6 H6 . . 119.2 ?
C6 C7 H7 . . 119.6 ?
C6 C7 C8 . . 120.73(10) ?
C8 C7 H7 . . 119.6 ?
C7 C8 H8 . . 120.0 ?
C9 C8 C7 . . 119.95(10) ?
C9 C8 H8 . . 120.0 ?
C8 C9 H9 . . 119.3 ?
C8 C9 C10 . . 121.38(11) ?
C10 C9 H9 . . 119.3 ?
C9 C10 C5 . . 118.80(9) ?
C11 C10 C5 . . 119.30(10) ?
C11 C10 C9 . . 121.90(11) ?
C10 C11 C10 2 . 121.84(14) ?
C10 C11 H11 2 . 119.1 ?
C10 C11 H11 . . 119.1 ?
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
N1 C1 . 1.3345(12) ?
N1 C1 2 1.3345(12) ?
C1 H1 . 0.9300 ?
C1 C2 . 1.3840(15) ?
C2 H2 . 0.9300 ?
C2 C3 . 1.3881(12) ?
C3 C4 . 1.4951(19) ?
C4 C5 2 1.4088(12) ?
C4 C5 . 1.4088(12) ?
C5 C6 . 1.4259(14) ?
C5 C10 . 1.4362(16) ?
C6 H6 . 0.9300 ?
C6 C7 . 1.3579(15) ?
C7 H7 . 0.9300 ?
C7 C8 . 1.4158(16) ?
C8 H8 . 0.9300 ?
C8 C9 . 1.3534(16) ?
C9 H9 . 0.9300 ?
C9 C10 . 1.4284(15) ?
C10 C11 . 1.3920(13) ?
C11 H11 . 0.9300 ?
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
C7 H7 Cg 5_666 0.93 2.74 3.5606(12) 148
C7 H7 Cg 6_666 0.93 2.74 3.5606(12) 148
