#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/31/2013152.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_2013152
loop_
_publ_author_name
'Holmes, Brian T.'
'Padgett, Clifford W.'
'Pennington, William T.'
_publ_section_title
;
 1,2,4,5-Tetrakis(2-vinylpyridyl)benzene--dichloromethane (1/2)
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o114
_journal_page_last               o116
_journal_paper_doi               10.1107/S0108270103001276
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C34 H26 N4, 2C H2 Cl2'
_chemical_formula_moiety         'C34 H26 N4, 2C H2 Cl2'
_chemical_formula_structural     'C34 H26 N4, 2C H2 Cl2'
_chemical_formula_sum            'C36 H30 Cl4 N4'
_chemical_formula_weight         660.44
_chemical_name_common
'1,2,4,5-tetrakis(2'-vinylpyridyl)benzene-dichloromethane (1:2)'
_chemical_name_systematic
' 1,2,4,5-tetrakis(2'-vinylpyridyl)benzene-dichloromethane (1:2)'
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 99.822(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.928(2)
_cell_length_b                   18.596(4)
_cell_length_c                   10.015(2)
_cell_measurement_reflns_used    8789
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.3714
_cell_measurement_theta_min      2.8250
_cell_volume                     1638.4(6)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2001)'
_computing_data_collection       'CrystalClear(Rigaku Corp., 2001)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2000)'
_computing_structure_solution    'SHELXTL, (Sheldrick,2000)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Mercury AFC8S'
_diffrn_measurement_method       ω
_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  0.0864
_diffrn_reflns_av_sigmaI/netI    0.0643
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15828
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.01
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.393
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.6757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(REQABA; Jacobson, 1998)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.408
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0653
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0125P)²+1.973P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1369
_reflns_number_gt                2172
_reflns_number_total             3339
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ga1001.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2013152
_cod_database_fobs_code          2013152
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_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
_atom_site_type_symbol
N1 -0.0891(3) 0.63113(15) 0.4618(3) 0.0548(7) Uani d . 1 . . N
N2 0.2441(4) 0.67215(17) 0.0440(3) 0.0634(8) Uani d . 1 . . N
C1 0.4369(3) 0.54020(16) 0.3839(3) 0.0408(7) Uani d . 1 . . C
C2 0.3587(3) 0.53603(16) 0.4954(3) 0.0409(7) Uani d . 1 . . C
C3 0.4262(4) 0.49630(17) 0.6081(3) 0.0447(7) Uani d . 1 . . C
H1 0.367(3) 0.4935(16) 0.683(3) 0.052(9) Uiso d . 1 . . H
C4 0.2099(4) 0.57042(18) 0.4919(3) 0.0466(7) Uani d . 1 . . C
H2 0.165(4) 0.5930(18) 0.404(4) 0.066(10) Uiso d . 1 . . H
C5 0.1285(4) 0.57177(19) 0.5897(4) 0.0529(8) Uani d . 1 . . C
H3 0.168(4) 0.5526(18) 0.676(4) 0.067(11) Uiso d . 1 . . H
C6 -0.0233(3) 0.60410(17) 0.5814(3) 0.0469(7) Uani d . 1 . . C
C7 -0.0950(4) 0.6056(2) 0.6927(4) 0.0648(10) Uani d . 1 . . C
H4 -0.047(4) 0.587(2) 0.775(4) 0.077(13) Uiso d . 1 . . H
C8 -0.2377(5) 0.6352(2) 0.6832(5) 0.0739(12) Uani d . 1 . . C
H5 -0.285(5) 0.635(2) 0.762(5) 0.105(15) Uiso d . 1 . . H
C9 -0.3043(5) 0.6629(2) 0.5623(5) 0.0685(11) Uani d . 1 . . C
H6 -0.406(5) 0.681(2) 0.544(4) 0.097(14) Uiso d . 1 . . H
C10 -0.2282(4) 0.6597(2) 0.4557(4) 0.0634(10) Uani d . 1 . . C
H7 -0.265(4) 0.6750(18) 0.367(4) 0.061(11) Uiso d . 1 . . H
C11 0.3776(4) 0.58315(18) 0.2636(3) 0.0455(7) Uani d . 1 . . C
H8 0.287(4) 0.6096(18) 0.269(3) 0.068(11) Uiso d . 1 . . H
C12 0.4348(4) 0.5911(2) 0.1521(3) 0.0566(9) Uani d . 1 . . C
H9 0.533(5) 0.569(2) 0.140(4) 0.087(13) Uiso d . 1 . . H
C13 0.3722(4) 0.63698(19) 0.0368(3) 0.0496(8) Uani d . 1 . . C
C14 0.4410(5) 0.6431(3) -0.0756(4) 0.0910(16) Uani d . 1 . . C
H10 0.525(6) 0.617(3) -0.075(5) 0.13(2) Uiso d . 1 . . H
C15 0.3791(6) 0.6869(3) -0.1812(5) 0.0929(17) Uani d . 1 . . C
H11 0.425(6) 0.693(3) -0.247(6) 0.14(2) Uiso d . 1 . . H
C16 0.2519(5) 0.7233(2) -0.1738(4) 0.0693(11) Uani d . 1 . . C
H12 0.208(4) 0.754(2) -0.251(4) 0.081(12) Uiso d . 1 . . H
C17 0.1882(6) 0.7145(2) -0.0602(4) 0.0780(13) Uani d . 1 . . C
H13 0.108(5) 0.735(2) -0.053(4) 0.083(14) Uiso d . 1 . . H
Cl1 -0.18376(12) 0.52390(6) 0.04942(11) 0.0779(3) Uani d . 1 . . Cl
Cl2 -0.14710(16) 0.67646(6) 0.10044(15) 0.1020(5) Uani d . 1 . . Cl
H15 0.023(5) 0.591(2) 0.104(4) 0.083(13) Uiso d . 1 . . H
H14 -0.062(5) 0.585(2) 0.230(5) 0.102(16) Uiso d . 1 . . H
C18 -0.0699(5) 0.5913(2) 0.1369(5) 0.0692(11) Uani d . 1 . . C
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'
Cl Cl 0.1484 0.1585 '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
C6 N1 C10 . . 116.8(3) y
C13 N2 C17 . . 117.3(3) y
C3 C1 C2 3_666 . 118.4(3) y
C3 C1 C11 3_666 . 120.3(3) y
C2 C1 C11 . . 121.3(3) y
C3 C2 C1 . . 117.6(3) y
C3 C2 C4 . . 120.9(3) y
C1 C2 C4 . . 121.5(3) y
C1 C3 C2 3_666 . 124.0(3) y
C1 C3 H1 3_666 . 120.5(18) ?
C2 C3 H1 . . 115.4(18) ?
C5 C4 C2 . . 127.0(3) y
C5 C4 H2 . . 117(2) ?
C2 C4 H2 . . 116(2) ?
C4 C5 C6 . . 125.8(3) y
C4 C5 H3 . . 121(2) ?
C6 C5 H3 . . 114(2) ?
N1 C6 C7 . . 121.5(3) y
N1 C6 C5 . . 117.6(3) y
C7 C6 C5 . . 120.9(3) y
C8 C7 C6 . . 120.3(4) n
C8 C7 H4 . . 120(2) ?
C6 C7 H4 . . 120(2) ?
C9 C8 C7 . . 118.3(4) n
C9 C8 H5 . . 124(3) ?
C7 C8 H5 . . 118(3) ?
C8 C9 C10 . . 118.8(4) n
C8 C9 H6 . . 124(3) ?
C10 C9 H6 . . 117(3) ?
N1 C10 C9 . . 124.3(4) y
N1 C10 H7 . . 110(2) ?
C9 C10 H7 . . 126(2) ?
C12 C11 C1 . . 128.4(3) y
C12 C11 H8 . . 117(2) ?
C1 C11 H8 . . 115(2) ?
C11 C12 C13 . . 125.7(3) y
C11 C12 H9 . . 123(2) ?
C13 C12 H9 . . 111(2) ?
N2 C13 C14 . . 120.8(3) y
N2 C13 C12 . . 117.3(3) y
C14 C13 C12 . . 121.9(3) n
C15 C14 C13 . . 120.1(4) n
C15 C14 H10 . . 124(4) ?
C13 C14 H10 . . 116(4) ?
C16 C15 C14 . . 119.5(4) n
C16 C15 H11 . . 121(4) ?
C14 C15 H11 . . 120(4) ?
C15 C16 C17 . . 117.7(4) n
C15 C16 H12 . . 118(2) ?
C17 C16 H12 . . 124(2) ?
N2 C17 C16 . . 124.7(4) y
N2 C17 H13 . . 114(3) ?
C16 C17 H13 . . 121(3) ?
Cl2 C18 Cl1 . . 111.8(2) y
Cl2 C18 H15 . . 106(3) ?
Cl1 C18 H15 . . 107(2) ?
Cl2 C18 H14 . . 106(3) ?
Cl1 C18 H14 . . 111(3) ?
H15 C18 H14 . . 115(4) ?
C18 Cl2 C9 . 4_575 174.1(2) y
C18 Cl2 C10 . 4_575 162.3(2) y
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 C6 . 1.338(4) y
N1 C10 . 1.342(4) y
N2 C13 . 1.330(4) n
N2 C17 . 1.335(5) n
C1 C3 3_666 1.388(4) y
C1 C2 . 1.417(4) y
C1 C11 . 1.467(4) y
C2 C3 . 1.397(4) y
C2 C4 . 1.469(4) y
C3 C1 3_666 1.388(4) ?
C3 H1 . 0.99(3) ?
C4 C5 . 1.316(4) y
C4 H2 . 1.00(3) ?
C5 C6 . 1.472(4) y
C5 H3 . 0.94(3) ?
C6 C7 . 1.378(5) y
C7 C8 . 1.376(5) y
C7 H4 . 0.92(4) ?
C8 C9 . 1.356(6) y
C8 H5 . 0.96(5) ?
C9 C10 . 1.361(5) y
C9 H6 . 0.96(4) ?
C10 H7 . 0.93(3) ?
C11 C12 . 1.313(4) n
C11 H8 . 0.96(4) ?
C12 C13 . 1.468(4) n
C12 H9 . 0.99(4) ?
C13 C14 . 1.376(5) n
C14 C15 . 1.374(6) n
C14 H10 . 0.90(5) ?
C15 C16 . 1.335(6) n
C15 H11 . 0.84(6) ?
C16 C17 . 1.366(6) n
C16 H12 . 0.98(4) ?
C17 H13 . 0.82(4) ?
Cl1 C18 . 1.752(4) y
Cl2 C18 . 1.741(4) y
Cl2 C9 4_575 3.295(4) y
Cl2 C10 4_575 3.399(4) y
C18 H15 . 0.94(4) ?
C18 H14 . 0.93(5) ?
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
C18 H14 N1 . 0.93(5) 2.52(5) 3.371(6) 152(4)
C18 H15 N2 . 0.94(4) 2.64(4) 3.445(6) 144(3)
C16 H12 N2 4_575 0.98(4) 2.54(4) 3.420(5) 149(3)
C5 H3 Cl1 3_566 0.94(3) 3.08(4) 3.982(4) 161(3)
C12 H9 Cl1 1_655 0.99(4) 2.95(4) 3.926(4) 167(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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C3 C1 C2 C3 3_666 . 1.2(5)
C11 C1 C2 C3 . . -177.4(3)
C3 C1 C2 C4 3_666 . -177.1(3)
C11 C1 C2 C4 . . 4.2(4)
C1 C2 C3 C1 . 3_666 -1.3(5)
C4 C2 C3 C1 . 3_666 177.1(3)
C3 C2 C4 C5 . . 3.5(5)
C1 C2 C4 C5 . . -178.2(3)
C2 C4 C5 C6 . . -177.3(3)
C10 N1 C6 C7 . . -0.1(5)
C10 N1 C6 C5 . . 179.3(3)
C4 C5 C6 N1 . . 4.0(5)
C4 C5 C6 C7 . . -176.6(4)
N1 C6 C7 C8 . . 0.1(6)
C5 C6 C7 C8 . . -179.2(4)
C6 C7 C8 C9 . . -0.4(7)
C7 C8 C9 C10 . . 0.5(6)
C6 N1 C10 C9 . . 0.3(6)
C8 C9 C10 N1 . . -0.5(6)
C3 C1 C11 C12 3_666 . 2.9(5)
C2 C1 C11 C12 . . -178.5(4)
C1 C11 C12 C13 . . -177.8(3)
C17 N2 C13 C14 . . -1.5(6)
C17 N2 C13 C12 . . 179.3(4)
C11 C12 C13 N2 . . -1.9(6)
C11 C12 C13 C14 . . 178.9(4)
N2 C13 C14 C15 . . 1.1(8)
C12 C13 C14 C15 . . -179.7(5)
C13 C14 C15 C16 . . 0.0(9)
C14 C15 C16 C17 . . -0.5(8)
C13 N2 C17 C16 . . 0.9(7)
C15 C16 C17 N2 . . 0.1(8)
