#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/28/2232859.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_2232859
loop_
_publ_author_name
'Akerman, Matthew P.'
'Grimmer, Craig D.'
'Nikolayenko, Varvara I.'
'Reddy, Desigan'
_publ_section_title
;
 1,4-Bis[(2,2':6',2''-terpyridin-4'-yl)oxy]butane
;
_journal_coeditor_code           LR2036
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3478
_journal_page_last               o3479
_journal_paper_doi               10.1107/S1600536811050343
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C34 H28 N6 O2'
_chemical_formula_moiety         'C34 H28 N6 O2'
_chemical_formula_sum            'C34 H28 N6 O2'
_chemical_formula_weight         552.62
_chemical_name_systematic
;
1,4-Bis[(2,2':6',2''-terpyridin-4'-yl)oxy]butane
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                72.580(3)
_cell_angle_beta                 78.561(3)
_cell_angle_gamma                77.438(3)
_cell_formula_units_Z            1
_cell_length_a                   6.3678(2)
_cell_length_b                   10.5088(4)
_cell_length_c                   10.9216(3)
_cell_measurement_reflns_used    4604
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.2
_cell_measurement_theta_min      3.2
_cell_volume                     673.64(4)
_computing_cell_refinement
'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_collection
'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.825
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur 2 CCD'
_diffrn_measurement_method       'omega scans at fixed theta angles'
_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  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10771
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         34.20
_diffrn_reflns_theta_min         3.21
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9742
_exptl_absorpt_correction_T_min  0.9657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       triangular
_exptl_crystal_F_000             290
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.430
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4604
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1033P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1480
_reflns_number_gt                3678
_reflns_number_total             4604
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lr2036.cif
_cod_data_source_block           I
_cod_database_code               2232859
_cod_database_fobs_code          2232859
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
C C1 0.91969(13) 0.45081(8) 0.20750(8) 0.01459(17) Uani d . 1 1
C C2 0.99907(14) 0.57692(9) 0.12469(8) 0.01538(17) Uani d . 1 1
C C3 1.21800(15) 0.57653(9) 0.07304(9) 0.01893(18) Uani d . 1 1
H H3 1.3198 0.4946 0.0869 0.023 Uiso calc R 1 1
C C4 1.28436(16) 0.69785(10) 0.00112(9) 0.0218(2) Uani d . 1 1
H H4 1.4330 0.7009 -0.0331 0.026 Uiso calc R 1 1
C C5 1.12985(16) 0.81461(10) -0.01999(9) 0.0227(2) Uani d . 1 1
H H5 1.1698 0.8990 -0.0699 0.027 Uiso calc R 1 1
C C6 0.91517(17) 0.80504(9) 0.03359(10) 0.0231(2) Uani d . 1 1
H H6 0.8093 0.8850 0.0179 0.028 Uiso calc R 1 1
C C7 0.70581(14) 0.45958(9) 0.27116(8) 0.01544(17) Uani d . 1 1
H H7 0.6095 0.5438 0.2593 0.019 Uiso calc R 1 1
C C8 0.63836(13) 0.34181(9) 0.35221(8) 0.01472(17) Uani d . 1 1
C C9 0.78076(13) 0.21929(8) 0.36168(8) 0.01555(17) Uani d . 1 1
H H9 0.7374 0.1368 0.4146 0.019 Uiso calc R 1 1
C C10 0.98796(13) 0.22108(8) 0.29156(8) 0.01479(17) Uani d . 1 1
C C11 1.14276(14) 0.09254(8) 0.29357(8) 0.01510(17) Uani d . 1 1
C C12 1.36485(14) 0.08795(9) 0.28696(9) 0.01945(19) Uani d . 1 1
H H12 1.4194 0.1663 0.2839 0.023 Uiso calc R 1 1
C C13 1.50515(15) -0.03274(10) 0.28492(10) 0.0221(2) Uani d . 1 1
H H13 1.6569 -0.0394 0.2832 0.026 Uiso calc R 1 1
C C14 1.41963(15) -0.14337(9) 0.28550(10) 0.0225(2) Uani d . 1 1
H H14 1.5118 -0.2265 0.2808 0.027 Uiso calc R 1 1
C C15 1.19601(15) -0.12984(9) 0.29316(10) 0.0213(2) Uani d . 1 1
H H15 1.1382 -0.2063 0.2943 0.026 Uiso calc R 1 1
C C16 0.29097(13) 0.46356(9) 0.41509(9) 0.01583(17) Uani d . 1 1
H H16A 0.2626 0.5046 0.3244 0.019 Uiso calc R 1 1
H H16B 0.3543 0.5275 0.4417 0.019 Uiso calc R 1 1
C C17 0.08210(13) 0.43460(8) 0.50317(8) 0.01595(18) Uani d . 1 1
H H17A 0.1122 0.3928 0.5934 0.019 Uiso calc R 1 1
H H17B 0.0207 0.3699 0.4764 0.019 Uiso calc R 1 1
N N1 1.06151(11) 0.33489(7) 0.21789(7) 0.01511(16) Uani d . 1 1
N N2 0.84919(13) 0.68991(8) 0.10593(8) 0.02008(17) Uani d . 1 1
N N3 1.05674(12) -0.01556(7) 0.29902(8) 0.01867(17) Uani d . 1 1
O O1 0.43840(10) 0.33755(6) 0.42503(6) 0.01732(15) Uani d . 1 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'
O O 0.0106 0.0060 '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
N1 C1 C7 . . 123.79(8)
N1 C1 C2 . . 117.13(7)
C7 C1 C2 . . 119.07(8)
N2 C2 C3 . . 122.59(8)
N2 C2 C1 . . 116.08(8)
C3 C2 C1 . . 121.31(8)
C4 C3 C2 . . 118.85(9)
C4 C3 H3 . . 120.6
C2 C3 H3 . . 120.6
C5 C4 C3 . . 118.82(9)
C5 C4 H4 . . 120.6
C3 C4 H4 . . 120.6
C4 C5 C6 . . 118.33(8)
C4 C5 H5 . . 120.8
C6 C5 H5 . . 120.8
N2 C6 C5 . . 123.71(9)
N2 C6 H6 . . 118.1
C5 C6 H6 . . 118.1
C8 C7 C1 . . 118.07(8)
C8 C7 H7 . . 121.0
C1 C7 H7 . . 121.0
O1 C8 C7 . . 123.93(8)
O1 C8 C9 . . 116.87(7)
C7 C8 C9 . . 119.20(8)
C10 C9 C8 . . 118.14(8)
C10 C9 H9 . . 120.9
C8 C9 H9 . . 120.9
N1 C10 C9 . . 123.81(8)
N1 C10 C11 . . 115.91(7)
C9 C10 C11 . . 120.27(8)
N3 C11 C12 . . 122.95(8)
N3 C11 C10 . . 116.45(7)
C12 C11 C10 . . 120.57(8)
C13 C12 C11 . . 118.97(8)
C13 C12 H12 . . 120.5
C11 C12 H12 . . 120.5
C14 C13 C12 . . 118.66(8)
C14 C13 H13 . . 120.7
C12 C13 H13 . . 120.7
C13 C14 C15 . . 118.40(8)
C13 C14 H14 . . 120.8
C15 C14 H14 . . 120.8
N3 C15 C14 . . 124.01(8)
N3 C15 H15 . . 118.0
C14 C15 H15 . . 118.0
O1 C16 C17 . . 107.75(7)
O1 C16 H16A . . 110.2
C17 C16 H16A . . 110.2
O1 C16 H16B . . 110.2
C17 C16 H16B . . 110.2
H16A C16 H16B . . 108.5
C16 C17 C17 . 2_566 110.24(9)
C16 C17 H17A . . 109.6
C17 C17 H17A 2_566 . 109.6
C16 C17 H17B . . 109.6
C17 C17 H17B 2_566 . 109.6
H17A C17 H17B . . 108.1
C1 N1 C10 . . 116.83(7)
C6 N2 C2 . . 117.68(8)
C15 N3 C11 . . 116.94(8)
C8 O1 C16 . . 117.00(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.3385(10)
C1 C7 . 1.3982(12)
C1 C2 . 1.4907(12)
C2 N2 . 1.3423(11)
C2 C3 . 1.3960(12)
C3 C4 . 1.3871(13)
C3 H3 . 0.9500
C4 C5 . 1.3865(13)
C4 H4 . 0.9500
C5 C6 . 1.3887(14)
C5 H5 . 0.9500
C6 N2 . 1.3348(12)
C6 H6 . 0.9500
C7 C8 . 1.3872(12)
C7 H7 . 0.9500
C8 O1 . 1.3629(10)
C8 C9 . 1.3930(11)
C9 C10 . 1.3889(12)
C9 H9 . 0.9500
C10 N1 . 1.3473(11)
C10 C11 . 1.4860(12)
C11 N3 . 1.3459(11)
C11 C12 . 1.3927(12)
C12 C13 . 1.3869(12)
C12 H12 . 0.9500
C13 C14 . 1.3848(13)
C13 H13 . 0.9500
C14 C15 . 1.3881(13)
C14 H14 . 0.9500
C15 N3 . 1.3390(11)
C15 H15 . 0.9500
C16 O1 . 1.4354(10)
C16 C17 . 1.5101(12)
C16 H16A . 0.9900
C16 H16B . 0.9900
C17 C17 2_566 1.5278(16)
C17 H17A . 0.9900
C17 H17B . 0.9900
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 N3 1_655 0.950 2.66 3.5920(10) 168.4 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
N1 C1 C2 N2 . 174.04(7)
C7 C1 C2 N2 . -7.06(12)
N1 C1 C2 C3 . -7.51(12)
C7 C1 C2 C3 . 171.39(8)
N2 C2 C3 C4 . 1.01(14)
C1 C2 C3 C4 . -177.34(8)
C2 C3 C4 C5 . -1.79(14)
C3 C4 C5 C6 . 0.89(14)
C4 C5 C6 N2 . 0.94(15)
N1 C1 C7 C8 . 1.61(13)
C2 C1 C7 C8 . -177.21(7)
C1 C7 C8 O1 . 176.41(7)
C1 C7 C8 C9 . -3.43(12)
O1 C8 C9 C10 . -178.11(7)
C7 C8 C9 C10 . 1.73(12)
C8 C9 C10 N1 . 2.05(13)
C8 C9 C10 C11 . -177.24(7)
N1 C10 C11 N3 . -143.94(8)
C9 C10 C11 N3 . 35.40(11)
N1 C10 C11 C12 . 34.59(12)
C9 C10 C11 C12 . -146.06(9)
N3 C11 C12 C13 . 0.47(15)
C10 C11 C12 C13 . -177.97(8)
C11 C12 C13 C14 . 1.97(15)
C12 C13 C14 C15 . -2.45(15)
C13 C14 C15 N3 . 0.56(16)
O1 C16 C17 C17 2_566 179.99(8)
C7 C1 N1 C10 . 1.97(12)
C2 C1 N1 C10 . -179.19(7)
C9 C10 N1 C1 . -3.86(12)
C11 C10 N1 C1 . 175.46(7)
C5 C6 N2 C2 . -1.74(15)
C3 C2 N2 C6 . 0.74(13)
C1 C2 N2 C6 . 179.17(8)
C14 C15 N3 C11 . 1.81(15)
C12 C11 N3 C15 . -2.32(14)
C10 C11 N3 C15 . 176.17(8)
C7 C8 O1 C16 . 0.40(12)
C9 C8 O1 C16 . -179.76(7)
C17 C16 O1 C8 . 179.98(7)
