#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/57/2235795.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_2235795
loop_
_publ_author_name
'Nikolayenko, Varvara I.'
'Akerman, Matthew P.'
'Grimmer, Craig D.'
'Reddy, Desigan'
_publ_section_title
;
 1,2-Bis[(2,2':6',2''-terpyridin-4'-yl)oxy]ethane
;
_journal_coeditor_code           FJ2578
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2384
_journal_page_last               o2385
_journal_paper_doi               10.1107/S1600536812030292
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C32 H24 N6 O2'
_chemical_formula_moiety         'C32 H24 N6 O2'
_chemical_formula_sum            'C32 H24 N6 O2'
_chemical_formula_weight         524.58
_chemical_name_common            L1
_chemical_name_systematic
;
1,2-Bis[(2,2':6',2''-terpyridin-4'-yl)oxy]ethane
;
_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           SHELXL97
_cell_angle_alpha                93.850(6)
_cell_angle_beta                 98.760(6)
_cell_angle_gamma                102.468(5)
_cell_formula_units_Z            1
_cell_length_a                   6.2576(6)
_cell_length_b                   10.0851(9)
_cell_length_c                   10.2388(9)
_cell_measurement_reflns_used    3364
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.8
_cell_measurement_theta_min      2.0
_cell_volume                     620.20(10)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2010)'
_computing_molecular_graphics    'WinGX (Farrugia, 1999)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω and φ scans'
_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  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0669
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8371
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.76
_diffrn_reflns_theta_min         2.02
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9955
_exptl_absorpt_correction_T_min  0.9820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             274
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.770
_refine_diff_density_min         -0.272
_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     181
_refine_ls_number_reflns         4459
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0616
_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)+(0.1018P)²+0.0609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1687
_refine_ls_wR_factor_ref         0.1816
_reflns_number_gt                3364
_reflns_number_total             4459
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2578.cif
_cod_data_source_block           I
_cod_database_code               2235795
_cod_database_fobs_code          2235795
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 0.8540(2) 0.33313(15) 0.60520(14) 0.0283(3) Uani d . 1 1
H H1 0.7963 0.3499 0.6837 0.034 Uiso calc R 1 1
C C2 1.0660(2) 0.30976(14) 0.61813(14) 0.0269(3) Uani d . 1 1
H H2 1.1508 0.3100 0.7034 0.032 Uiso calc R 1 1
C C3 1.1514(2) 0.28615(14) 0.50440(14) 0.0250(3) Uani d . 1 1
H H3 1.2977 0.2721 0.5101 0.030 Uiso calc R 1 1
C C4 1.0195(2) 0.28323(13) 0.38123(13) 0.0208(3) Uani d . 1 1
H H4 1.0724 0.2648 0.3013 0.025 Uiso calc R 1 1
C C5 0.80907(19) 0.30792(12) 0.37783(12) 0.0166(2) Uani d . 1 1
C C6 0.66344(19) 0.30803(12) 0.24834(11) 0.0162(2) Uani d . 1 1
C C7 0.5019(2) 0.38379(12) 0.24126(12) 0.0174(2) Uani d . 1 1
H H7 0.4845 0.4371 0.3173 0.021 Uiso calc R 1 1
C C8 0.36599(19) 0.37913(11) 0.11862(12) 0.0164(2) Uani d . 1 1
C C9 0.3930(2) 0.29829(12) 0.01032(12) 0.0175(2) Uani d . 1 1
H H9 0.2993 0.2913 -0.0733 0.021 Uiso calc R 1 1
C C10 0.56189(19) 0.22744(11) 0.02768(12) 0.0163(2) Uani d . 1 1
C C11 0.5964(2) 0.14184(12) -0.08808(12) 0.0176(2) Uani d . 1 1
C C12 0.7865(2) 0.09098(13) -0.08388(13) 0.0216(3) Uani d . 1 1
H H12 0.8959 0.1077 -0.0057 0.026 Uiso calc R 1 1
C C13 0.8136(2) 0.01537(14) -0.19586(14) 0.0263(3) Uani d . 1 1
H H13 0.9440 -0.0183 -0.1966 0.032 Uiso calc R 1 1
C C14 0.6474(3) -0.01030(14) -0.30669(14) 0.0286(3) Uani d . 1 1
H H14 0.6605 -0.0627 -0.3845 0.034 Uiso calc R 1 1
C C15 0.4620(3) 0.04248(14) -0.30107(14) 0.0277(3) Uani d . 1 1
H H15 0.3471 0.0234 -0.3765 0.033 Uiso calc R 1 1
C C16 0.07750(19) 0.45488(12) -0.01226(11) 0.0167(2) Uani d . 1 1
H H16A -0.0069 0.3610 -0.0461 0.020 Uiso calc R 1 1
H H16B 0.1703 0.4909 -0.0778 0.020 Uiso calc R 1 1
N N1 0.72577(19) 0.33330(12) 0.48743(11) 0.0235(2) Uani d . 1 1
N N2 0.69872(17) 0.23327(10) 0.14323(10) 0.0170(2) Uani d . 1 1
N N3 0.4356(2) 0.11876(11) -0.19559(11) 0.0231(2) Uani d . 1 1
O O1 0.21257(15) 0.45611(9) 0.11416(8) 0.0196(2) 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 C2 . . 123.44(13)
N1 C1 H1 . . 118.3
C2 C1 H1 . . 118.3
C3 C2 C1 . . 118.57(11)
C3 C2 H2 . . 120.7
C1 C2 H2 . . 120.7
C2 C3 C4 . . 118.90(12)
C2 C3 H3 . . 120.6
C4 C3 H3 . . 120.6
C5 C4 C3 . . 118.52(12)
C5 C4 H4 . . 120.7
C3 C4 H4 . . 120.7
N1 C5 C4 . . 123.13(10)
N1 C5 C6 . . 116.44(10)
C4 C5 C6 . . 120.42(11)
N2 C6 C7 . . 123.58(10)
N2 C6 C5 . . 116.82(9)
C7 C6 C5 . . 119.60(10)
C6 C7 C8 . . 117.85(10)
C6 C7 H7 . . 121.1
C8 C7 H7 . . 121.1
O1 C8 C9 . . 123.90(10)
O1 C8 C7 . . 116.52(10)
C9 C8 C7 . . 119.58(10)
C8 C9 C10 . . 118.00(10)
C8 C9 H9 . . 121.0
C10 C9 H9 . . 121.0
N2 C10 C9 . . 123.59(10)
N2 C10 C11 . . 117.52(10)
C9 C10 C11 . . 118.88(10)
N3 C11 C12 . . 122.67(11)
N3 C11 C10 . . 116.21(10)
C12 C11 C10 . . 121.12(10)
C13 C12 C11 . . 118.78(11)
C13 C12 H12 . . 120.6
C11 C12 H12 . . 120.6
C14 C13 C12 . . 118.95(12)
C14 C13 H13 . . 120.5
C12 C13 H13 . . 120.5
C15 C14 C13 . . 118.25(12)
C15 C14 H14 . . 120.9
C13 C14 H14 . . 120.9
N3 C15 C14 . . 123.72(12)
N3 C15 H15 . . 118.1
C14 C15 H15 . . 118.1
O1 C16 C16 . 2_565 105.29(11)
O1 C16 H16A . . 110.7
C16 C16 H16A 2_565 . 110.7
O1 C16 H16B . . 110.7
C16 C16 H16B 2_565 . 110.7
H16A C16 H16B . . 108.8
C5 N1 C1 . . 117.40(11)
C10 N2 C6 . . 117.30(9)
C15 N3 C11 . . 117.59(11)
C8 O1 C16 . . 116.69(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.3431(16)
C1 C2 . 1.385(2)
C1 H1 . 0.9500
C2 C3 . 1.381(2)
C2 H2 . 0.9500
C3 C4 . 1.3928(16)
C3 H3 . 0.9500
C4 C5 . 1.3879(16)
C4 H4 . 0.9500
C5 N1 . 1.3393(17)
C5 C6 . 1.4902(15)
C6 N2 . 1.3457(15)
C6 C7 . 1.3889(15)
C7 C8 . 1.3972(15)
C7 H7 . 0.9500
C8 O1 . 1.3564(13)
C8 C9 . 1.3849(16)
C9 C10 . 1.3945(15)
C9 H9 . 0.9500
C10 N2 . 1.3404(14)
C10 C11 . 1.4891(16)
C11 N3 . 1.3437(14)
C11 C12 . 1.3895(17)
C12 C13 . 1.3865(18)
C12 H12 . 0.9500
C13 C14 . 1.3859(19)
C13 H13 . 0.9500
C14 C15 . 1.384(2)
C14 H14 . 0.9500
C15 N3 . 1.3354(17)
C15 H15 . 0.9500
C16 O1 . 1.4318(13)
C16 C16 2_565 1.502(2)
C16 H16A . 0.9900
C16 H16B . 0.9900
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
N1 C1 C2 C3 . 0.4(2)
C1 C2 C3 C4 . -1.6(2)
C2 C3 C4 C5 . 1.72(19)
C3 C4 C5 N1 . -0.60(19)
C3 C4 C5 C6 . 179.03(11)
N1 C5 C6 N2 . -154.39(12)
C4 C5 C6 N2 . 25.96(17)
N1 C5 C6 C7 . 25.91(17)
C4 C5 C6 C7 . -153.74(12)
N2 C6 C7 C8 . 1.52(19)
C5 C6 C7 C8 . -178.80(11)
C6 C7 C8 O1 . -178.82(11)
C6 C7 C8 C9 . 1.27(18)
O1 C8 C9 C10 . 178.08(11)
C7 C8 C9 C10 . -2.02(18)
C8 C9 C10 N2 . 0.09(19)
C8 C9 C10 C11 . -178.94(11)
N2 C10 C11 N3 . 168.96(11)
C9 C10 C11 N3 . -11.94(18)
N2 C10 C11 C12 . -11.79(18)
C9 C10 C11 C12 . 167.31(12)
N3 C11 C12 C13 . 1.2(2)
C10 C11 C12 C13 . -178.02(12)
C11 C12 C13 C14 . -1.9(2)
C12 C13 C14 C15 . 0.8(2)
C13 C14 C15 N3 . 1.2(2)
C4 C5 N1 C1 . -0.62(19)
C6 C5 N1 C1 . 179.74(12)
C2 C1 N1 C5 . 0.7(2)
C9 C10 N2 C6 . 2.55(18)
C11 C10 N2 C6 . -178.40(11)
C7 C6 N2 C10 . -3.38(18)
C5 C6 N2 C10 . 176.93(10)
C14 C15 N3 C11 . -1.9(2)
C12 C11 N3 C15 . 0.7(2)
C10 C11 N3 C15 . 179.90(13)
C9 C8 O1 C16 . -1.95(18)
C7 C8 O1 C16 . 178.14(10)
C16 C16 O1 C8 2_565 178.97(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 86062380
