#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006959.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_2006959
loop_
_publ_author_name
'Bennis, V.'
'Gallagher, J. F.'
_publ_section_title
;
 N---H\p(pyrrole) Intermolecular Interactions in
 1,4-Bis(di-2-pyrrolylmethyl)benzene
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              130
_journal_page_last               132
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C24 H22 N4'
_chemical_formula_sum            'C24 H22 N4'
_chemical_formula_weight         366.46
_chemical_name_common            1,4-bis(2,2'-dipyrromethyl)benzene
_chemical_name_systematic
;
1,4-bis(2,2'-dipyrromethyl)benzene
;
_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'
_cell_angle_alpha                90.00
_cell_angle_beta                 92.738(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.4806(12)
_cell_length_b                   13.8928(15)
_cell_length_c                   10.9886(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294.0(10)
_cell_measurement_theta_max      18.78
_cell_measurement_theta_min      7.74
_cell_volume                     988.2(2)
_computing_cell_refinement       'SET4 and CELDIM in CAD-4-PC Software'
_computing_data_collection       'CAD-4-PC Software (Enraf-Nonius, 1992)'
_computing_data_reduction        'DATRD2 in NRCVAX96 (Gabe et al., 1989)'
_computing_molecular_graphics
;
NRCVAX96, ORTEPII (Johnson, 1976), PLATON (Spek, 1997a) and
PLUTON (Spek, 1997b)
;
_computing_publication_material
'NRCVAX96, SHELXL97 and WordPerfect macro PRPCIF97 (Ferguson, 1997)'
_computing_structure_refinement  'NRCVAX96 and SHELXL97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      294.0(10)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_av_sigmaI/netI    0.1571
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2464
_diffrn_reflns_theta_full        27.4
_diffrn_reflns_theta_max         27.4
_diffrn_reflns_theta_min         2.36
_diffrn_standards_decay_%        'intensity variation: 1.0%'
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.153
_refine_ls_extinction_coef       0.0073(13)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_all   0.829
_refine_ls_goodness_of_fit_ref   0.829
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.829
_refine_ls_R_factor_all          0.218
_refine_ls_R_factor_obs          0.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0348P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.104
_refine_ls_wR_factor_ref         0.104
_reflns_number_gt                789
_reflns_number_total             2256
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    sk1144.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_database_code               2006959
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_type_symbol
C1 0.5304(4) 0.51650(19) 0.23524(19) 0.0432(7) Uani d . 1 C
C2 0.5157(4) 0.50657(17) 0.3731(2) 0.0365(6) Uani d . 1 C
C3 0.3293(4) 0.52051(18) 0.4269(2) 0.0428(7) Uani d . 1 C
C4 0.6865(4) 0.48554(18) 0.4486(2) 0.0424(7) Uani d . 1 C
C11 0.6696(4) 0.4419(2) 0.1829(2) 0.0443(7) Uani d . 1 C
C12 0.8403(4) 0.4509(2) 0.1161(2) 0.0588(8) Uani d . 1 C
C13 0.9094(4) 0.3569(2) 0.0886(2) 0.0658(9) Uani d . 1 C
C14 0.7808(5) 0.2943(2) 0.1394(2) 0.0631(8) Uani d . 1 C
N15 0.6358(3) 0.34593(17) 0.19636(19) 0.0555(6) Uani d . 1 N
C21 0.6002(4) 0.61569(19) 0.1999(2) 0.0417(7) Uani d . 1 C
C22 0.7503(4) 0.6736(2) 0.2482(2) 0.0532(8) Uani d . 1 C
C23 0.7675(4) 0.7550(2) 0.1716(3) 0.0589(8) Uani d . 1 C
C24 0.6255(5) 0.7436(2) 0.0794(3) 0.0602(8) Uani d . 1 C
N25 0.5239(3) 0.65918(17) 0.09629(18) 0.0549(6) Uani d . 1 N
H1 0.3915 0.5067 0.1981 0.052 Uiso calc R 1 H
H3 0.2119 0.5343 0.3780 0.051 Uiso calc R 1 H
H4 0.8137 0.4753 0.4150 0.051 Uiso calc R 1 H
H12 0.9006 0.5083 0.0927 0.071 Uiso calc R 1 H
H13 1.0228 0.3414 0.0437 0.079 Uiso calc R 1 H
H14 0.7896 0.2276 0.1362 0.076 Uiso calc R 1 H
H15 0.5367 0.3214 0.2354 0.067 Uiso calc R 1 H
H22 0.8291 0.6620 0.3197 0.064 Uiso calc R 1 H
H23 0.8589 0.8061 0.1829 0.071 Uiso calc R 1 H
H24 0.6009 0.7862 0.0150 0.072 Uiso calc R 1 H
H25 0.4263 0.6367 0.0487 0.066 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0508(17) 0.0478(19) 0.0316(14) -0.0007(15) 0.0071(11) 0.0008(14)
C2 0.0472(16) 0.0290(16) 0.0340(13) -0.0029(12) 0.0096(12) 0.0034(12)
C3 0.0456(17) 0.0493(18) 0.0334(14) 0.0000(14) 0.0026(12) 0.0054(14)
C4 0.0421(16) 0.0478(18) 0.0384(14) 0.0053(14) 0.0132(12) 0.0009(14)
C11 0.0596(19) 0.0404(18) 0.0333(15) -0.0034(15) 0.0069(13) 0.0015(14)
C12 0.069(2) 0.050(2) 0.0597(18) -0.0008(16) 0.0296(15) 0.0054(16)
C13 0.070(2) 0.067(3) 0.063(2) 0.0181(18) 0.0273(16) -0.0005(18)
C14 0.083(2) 0.0479(19) 0.059(2) 0.0178(19) 0.0087(17) -0.0037(17)
N15 0.0672(16) 0.0496(17) 0.0512(15) -0.0022(13) 0.0169(12) 0.0071(13)
C21 0.0544(18) 0.0400(17) 0.0311(15) 0.0009(15) 0.0061(13) -0.0003(14)
C22 0.0631(19) 0.0503(19) 0.0459(16) 0.0021(17) -0.0001(14) 0.0069(17)
C23 0.072(2) 0.049(2) 0.0565(18) -0.0024(17) 0.0100(17) 0.0008(17)
C24 0.089(2) 0.0444(19) 0.0490(18) 0.0027(18) 0.0185(17) 0.0105(16)
N25 0.0765(17) 0.0542(16) 0.0337(13) 0.0001(14) -0.0007(11) 0.0034(13)
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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-2 2 -2
-2 2 2
-1 -1 5
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
_geom_angle_publ_flag
C2 C1 C11 . 112.5(2) ?
C2 C1 C21 . 111.8(2) ?
C11 C1 C21 . 109.78(19) ?
C1 C2 C3 . 120.5(2) ?
C1 C2 C4 . 121.8(2) ?
C3 C2 C4 . 117.6(2) ?
C2 C3 C4 3_666 121.5(2) ?
C2 C4 C3 3_666 120.8(2) ?
N15 C11 C1 . 122.1(2) yes
N15 C11 C12 . 106.6(2) yes
C1 C11 C12 . 131.3(3) yes
C11 C12 C13 . 107.7(3) yes
C12 C13 C14 . 107.4(3) ?
C13 C14 N15 . 107.8(3) ?
C11 N15 C14 . 110.4(2) yes
N25 C21 C1 . 121.3(2) yes
N25 C21 C22 . 106.9(2) yes
C1 C21 C22 . 131.5(2) yes
C21 C22 C23 . 108.5(2) yes
C22 C23 C24 . 106.5(3) ?
C23 C24 N25 . 108.4(3) ?
C21 N25 C24 . 109.7(2) yes
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 C11 . 1.505(3) ?
C1 C21 . 1.507(3) ?
C1 C2 . 1.529(3) ?
C2 C3 . 1.384(3) ?
C2 C4 . 1.382(3) ?
C3 C4 3_666 1.379(3) ?
N15 C11 . 1.361(3) yes
N15 C14 . 1.358(3) yes
C11 C12 . 1.363(3) yes
C12 C13 . 1.417(4) yes
C13 C14 . 1.344(3) yes
N25 C21 . 1.361(3) yes
N25 C24 . 1.363(3) yes
C21 C22 . 1.351(3) yes
C22 C23 . 1.417(3) yes
C23 C24 . 1.345(4) yes
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
N25 H25 Cg1 3_665 0.86 2.42 3.219(3) 154 yes
N15 H15 Cg2 2_645 0.86 2.52 3.324(3) 156 yes
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_4
_geom_torsion
C11 C1 C2 C4 . 40.6(3)
C21 C1 C2 C4 . -83.5(3)
C11 C1 C2 C3 . -140.7(2)
C21 C1 C2 C3 . 95.2(3)
C4 C2 C3 C4 3_666 0.5(4)
C1 C2 C3 C4 3_666 -178.2(2)
C3 C2 C4 C3 3_666 -0.5(4)
C1 C2 C4 C3 3_666 178.2(2)
C21 C1 C11 N15 . -177.0(2)
C2 C1 C11 N15 . 57.8(3)
C21 C1 C11 C12 . 2.0(4)
C2 C1 C11 C12 . -123.2(3)
N15 C11 C12 C13 . 0.2(3)
C1 C11 C12 C13 . -178.9(3)
C11 C12 C13 C14 . -0.3(3)
C12 C13 C14 N15 . 0.2(3)
C13 C14 N15 C11 . 0.0(3)
C12 C11 N15 C14 . -0.1(3)
C1 C11 N15 C14 . 179.1(2)
C11 C1 C21 C22 . -82.0(3)
C2 C1 C21 C22 . 43.6(4)
C11 C1 C21 N25 . 90.7(3)
C2 C1 C21 N25 . -143.6(2)
N25 C21 C22 C23 . -0.3(3)
C1 C21 C22 C23 . 173.3(2)
C21 C22 C23 C24 . 0.3(3)
C22 C23 C24 N25 . -0.2(3)
C22 C21 N25 C24 . 0.1(3)
C1 C21 N25 C24 . -174.2(2)
C23 C24 N25 C21 . 0.1(3)