#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:24:23 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301857 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/90/7119012.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7119012
loop_
_publ_author_name
'Helena Isla'
'Monika Srebro-Hooper'
'Marion Jean'
'Nicolas Vanthuyne'
'Thierry Roisnel'
'Jamie L. Lunkley'
'Gilles Muller'
'J. A. Gareth Williams'
'Jochen Autschbach'
'Jeanne Crassous'
_publ_section_title
;
 Conformational changes and chiroptical switching of enantiopure
 bis-helicenic terpyridine upon Zn²⁺ binding
;
_journal_name_full               Chem.Commun.
_journal_page_first              5932
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C55 H31 N3'
_chemical_formula_sum            'C55 H31 N3'
_chemical_formula_weight         733.83
_space_group_crystal_system      orthorhombic
_space_group_IT_number           36
_space_group_name_Hall           'C 2c -2c'
_space_group_name_H-M_alt        'C c m 21'
_symmetry_space_group_name_Hall  'C 2c -2c'
_symmetry_space_group_name_H-M   'C c m 21'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2016-01-21 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9705(6)
_cell_length_b                   34.3796(16)
_cell_length_c                   8.1479(3)
_cell_measurement_reflns_used    7578
_cell_measurement_temperature    150
_cell_measurement_theta_max      74.94
_cell_measurement_theta_min      2.57
_cell_measurement_wavelength     1.54178
_cell_volume                     3913.4(3)
_computing_cell_refinement       'APEX2 (Bruker, 2014)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'CRYSCALc (T. Roisnel, local program, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images, thin slices'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            11539
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.057
_diffrn_reflns_theta_min         6.336
_exptl_absorpt_coefficient_mu    0.561
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       plate
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3300
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0949P)²+0.9985P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1355
_refine_ls_wR_factor_ref         0.1428
_reflns_number_gt                3015
_reflns_number_total             3300
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc01748g2.cif
_cod_data_source_block           HI103
_cod_database_code               7119012
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, z+1/2'
'x, -y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0910(3) 0.0000 0.2031(7) 0.0344(11) Uani 1 2 d S T P . .
H1 H -0.1563 0.0000 0.2357 0.041 Uiso 1 2 calc R U P . .
N2 N 0.0980(2) 0.0000 0.0996(5) 0.0231(8) Uani 1 2 d S T P . .
C3 C -0.0436(2) 0.03473(9) 0.1794(5) 0.0297(8) Uani 1 1 d . . . . .
H3 H -0.0747 0.0589 0.1987 0.036 Uiso 1 1 calc R U . . .
C4 C 0.0510(2) 0.03348(9) 0.1264(4) 0.0235(7) Uani 1 1 d . . . . .
C5 C 0.1054(2) 0.06987(9) 0.0957(4) 0.0234(7) Uani 1 1 d . . . . .
N6 N 0.06323(17) 0.10310(8) 0.1365(4) 0.0269(7) Uani 1 1 d . . . . .
C7 C 0.1115(2) 0.13673(9) 0.1131(4) 0.0263(7) Uani 1 1 d . . . . .
C8 C 0.0673(2) 0.17112(10) 0.1763(5) 0.0322(8) Uani 1 1 d . . . . .
H8 H 0.0042 0.1700 0.2196 0.039 Uiso 1 1 calc R U . . .
C9 C 0.1152(2) 0.20520(10) 0.1747(5) 0.0338(8) Uani 1 1 d . . . . .
H9 H 0.0865 0.2275 0.2230 0.041 Uiso 1 1 calc R U . . .
C10 C 0.2084(2) 0.20869(10) 0.1019(5) 0.0317(8) Uani 1 1 d . . . . .
C11 C 0.2594(3) 0.24422(10) 0.1194(5) 0.0371(9) Uani 1 1 d . . . . .
H11 H 0.2283 0.2664 0.1640 0.045 Uiso 1 1 calc R U . . .
C12 C 0.3522(3) 0.24648(10) 0.0725(5) 0.0378(9) Uani 1 1 d . . . . .
H12 H 0.3884 0.2690 0.0986 0.045 Uiso 1 1 calc R U . . .
C13 C 0.3962(3) 0.21553(10) -0.0153(4) 0.0314(8) Uani 1 1 d . . . . .
C14 C 0.4963(3) 0.21675(10) -0.0528(5) 0.0373(9) Uani 1 1 d . . . . .
H14 H 0.5326 0.2391 -0.0241 0.045 Uiso 1 1 calc R U . . .
C15 C 0.5392(2) 0.18701(11) -0.1273(5) 0.0343(9) Uani 1 1 d . . . . .
H15 H 0.6070 0.1859 -0.1319 0.041 Uiso 1 1 calc R U . . .
C16 C 0.4837(2) 0.15686(10) -0.2000(5) 0.0289(7) Uani 1 1 d . . . . .
C17 C 0.5292(2) 0.12655(11) -0.2916(5) 0.0339(8) Uani 1 1 d . . . . .
H17 H 0.5971 0.1249 -0.2925 0.041 Uiso 1 1 calc R U . . .
C18 C 0.4781(2) 0.10042(11) -0.3759(5) 0.0345(8) Uani 1 1 d . . . . .
H18 H 0.5094 0.0790 -0.4261 0.041 Uiso 1 1 calc R U . . .
C19 C 0.3763(2) 0.10457(10) -0.3913(5) 0.0312(8) Uani 1 1 d . . . . .
C20 C 0.3230(3) 0.08120(12) -0.4997(5) 0.0385(9) Uani 1 1 d . . . . .
H20 H 0.3537 0.0603 -0.5551 0.046 Uiso 1 1 calc R U . . .
C21 C 0.2277(3) 0.08796(13) -0.5268(5) 0.0429(10) Uani 1 1 d . . . . .
H21 H 0.1926 0.0716 -0.5990 0.051 Uiso 1 1 calc R U . . .
C22 C 0.1821(2) 0.11889(11) -0.4483(5) 0.0351(9) Uani 1 1 d . . . . .
H22 H 0.1172 0.1246 -0.4727 0.042 Uiso 1 1 calc R U . . .
C23 C 0.2309(2) 0.14112(10) -0.3357(5) 0.0289(8) Uani 1 1 d . . . . .
H23 H 0.1983 0.1614 -0.2797 0.035 Uiso 1 1 calc R U . . .
C24 C 0.3288(2) 0.13429(9) -0.3017(5) 0.0268(7) Uani 1 1 d . . . . .
C25 C 0.3833(2) 0.15738(10) -0.1848(4) 0.0249(7) Uani 1 1 d . . . . .
C26 C 0.3413(2) 0.18278(10) -0.0636(4) 0.0270(7) Uani 1 1 d . . . . .
C27 C 0.2499(2) 0.17679(9) 0.0197(5) 0.0261(7) Uani 1 1 d . . . . .
C28 C 0.2040(2) 0.13913(9) 0.0401(4) 0.0234(7) Uani 1 1 d . . . . .
C29 C 0.2476(2) 0.10259(9) 0.0065(4) 0.0237(7) Uani 1 1 d . . . . .
H29 H 0.3110 0.1017 -0.0357 0.028 Uiso 1 1 calc R U . . .
C30 C 0.1994(2) 0.06884(9) 0.0341(4) 0.0239(7) Uani 1 1 d . . . . .
H30 H 0.2292 0.0446 0.0119 0.029 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C3 C1 C3 119.9(4) 4 .
C3 C1 H1 120.0 4 .
C3 C1 H1 120.0 . .
C4 N2 C4 118.0(3) . 4
C1 C3 C4 118.3(3) . .
C1 C3 H3 120.9 . .
C4 C3 H3 120.9 . .
N2 C4 C3 122.8(3) . .
N2 C4 C5 116.4(3) . .
C3 C4 C5 120.8(3) . .
N6 C5 C30 121.7(3) . .
N6 C5 C4 117.1(3) . .
C30 C5 C4 121.1(3) . .
C5 N6 C7 118.7(2) . .
N6 C7 C28 124.1(3) . .
N6 C7 C8 116.2(3) . .
C28 C7 C8 119.6(3) . .
C9 C8 C7 120.0(3) . .
C9 C8 H8 120.0 . .
C7 C8 H8 120.0 . .
C8 C9 C10 121.8(3) . .
C8 C9 H9 119.1 . .
C10 C9 H9 119.1 . .
C27 C10 C11 120.7(3) . .
C27 C10 C9 120.3(3) . .
C11 C10 C9 119.0(3) . .
C12 C11 C10 120.1(3) . .
C12 C11 H11 120.0 . .
C10 C11 H11 120.0 . .
C11 C12 C13 120.8(3) . .
C11 C12 H12 119.6 . .
C13 C12 H12 119.6 . .
C26 C13 C12 120.0(3) . .
C26 C13 C14 119.5(3) . .
C12 C13 C14 120.5(3) . .
C15 C14 C13 120.9(3) . .
C15 C14 H14 119.5 . .
C13 C14 H14 119.5 . .
C14 C15 C16 120.3(3) . .
C14 C15 H15 119.9 . .
C16 C15 H15 119.9 . .
C25 C16 C15 119.8(3) . .
C25 C16 C17 119.9(3) . .
C15 C16 C17 120.3(3) . .
C18 C17 C16 121.3(3) . .
C18 C17 H17 119.4 . .
C16 C17 H17 119.4 . .
C17 C18 C19 120.5(3) . .
C17 C18 H18 119.7 . .
C19 C18 H18 119.7 . .
C20 C19 C24 119.1(3) . .
C20 C19 C18 121.5(3) . .
C24 C19 C18 119.3(3) . .
C21 C20 C19 121.3(4) . .
C21 C20 H20 119.4 . .
C19 C20 H20 119.4 . .
C20 C21 C22 119.9(4) . .
C20 C21 H21 120.0 . .
C22 C21 H21 120.0 . .
C23 C22 C21 120.3(3) . .
C23 C22 H22 119.9 . .
C21 C22 H22 119.9 . .
C22 C23 C24 121.2(3) . .
C22 C23 H23 119.4 . .
C24 C23 H23 119.4 . .
C23 C24 C19 118.0(3) . .
C23 C24 C25 122.9(3) . .
C19 C24 C25 119.0(3) . .
C16 C25 C26 118.2(3) . .
C16 C25 C24 117.2(3) . .
C26 C25 C24 124.4(3) . .
C13 C26 C25 116.8(3) . .
C13 C26 C27 117.1(3) . .
C25 C26 C27 126.0(3) . .
C10 C27 C28 117.2(3) . .
C10 C27 C26 118.1(3) . .
C28 C27 C26 124.3(3) . .
C29 C28 C7 114.7(3) . .
C29 C28 C27 125.1(3) . .
C7 C28 C27 119.9(3) . .
C30 C29 C28 120.6(3) . .
C30 C29 H29 119.7 . .
C28 C29 H29 119.7 . .
C29 C30 C5 120.0(3) . .
C29 C30 H30 120.0 . .
C5 C30 H30 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C3 1.379(4) 4
C1 C3 1.379(4) .
C1 H1 0.9500 .
N2 C4 1.343(3) .
N2 C4 1.343(3) 4
C3 C4 1.391(4) .
C3 H3 0.9500 .
C4 C5 1.485(4) .
C5 N6 1.327(4) .
C5 C30 1.406(4) .
N6 C7 1.352(4) .
C7 C28 1.426(4) .
C7 C8 1.430(5) .
C8 C9 1.349(5) .
C8 H8 0.9500 .
C9 C10 1.436(5) .
C9 H9 0.9500 .
C10 C27 1.410(5) .
C10 C11 1.421(5) .
C11 C12 1.354(5) .
C11 H11 0.9500 .
C12 C13 1.422(5) .
C12 H12 0.9500 .
C13 C26 1.418(5) .
C13 C14 1.432(5) .
C14 C15 1.331(5) .
C14 H14 0.9500 .
C15 C16 1.424(5) .
C15 H15 0.9500 .
C16 C25 1.407(4) .
C16 C17 1.431(5) .
C17 C18 1.338(5) .
C17 H17 0.9500 .
C18 C19 1.435(5) .
C18 H18 0.9500 .
C19 C20 1.407(5) .
C19 C24 1.420(5) .
C20 C21 1.370(5) .
C20 H20 0.9500 .
C21 C22 1.394(6) .
C21 H21 0.9500 .
C22 C23 1.375(5) .
C22 H22 0.9500 .
C23 C24 1.415(4) .
C23 H23 0.9500 .
C24 C25 1.455(5) .
C25 C26 1.444(5) .
C26 C27 1.460(5) .
C27 C28 1.455(4) .
C28 C29 1.423(4) .
C29 C30 1.360(4) .
C29 H29 0.9500 .
C30 H30 0.9500 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C3 C1 C3 C4 2.1(8) 4 . . .
C4 N2 C4 C3 -0.4(7) 4 . . .
C4 N2 C4 C5 179.9(2) 4 . . .
C1 C3 C4 N2 -0.9(6) . . . .
C1 C3 C4 C5 178.8(4) . . . .
N2 C4 C5 N6 -173.7(3) . . . .
C3 C4 C5 N6 6.6(5) . . . .
N2 C4 C5 C30 3.0(5) . . . .
C3 C4 C5 C30 -176.7(3) . . . .
C30 C5 N6 C7 2.1(5) . . . .
C4 C5 N6 C7 178.7(3) . . . .
C5 N6 C7 C28 2.8(5) . . . .
C5 N6 C7 C8 -173.1(3) . . . .
N6 C7 C8 C9 172.6(3) . . . .
C28 C7 C8 C9 -3.5(5) . . . .
C7 C8 C9 C10 3.7(6) . . . .
C8 C9 C10 C27 4.3(6) . . . .
C8 C9 C10 C11 -173.4(4) . . . .
C27 C10 C11 C12 -7.0(6) . . . .
C9 C10 C11 C12 170.7(4) . . . .
C10 C11 C12 C13 8.9(6) . . . .
C11 C12 C13 C26 3.8(6) . . . .
C11 C12 C13 C14 -174.9(4) . . . .
C26 C13 C14 C15 -2.3(5) . . . .
C12 C13 C14 C15 176.4(3) . . . .
C13 C14 C15 C16 12.5(6) . . . .
C14 C15 C16 C25 -3.7(5) . . . .
C14 C15 C16 C17 174.9(3) . . . .
C25 C16 C17 C18 6.0(5) . . . .
C15 C16 C17 C18 -172.5(3) . . . .
C16 C17 C18 C19 6.8(6) . . . .
C17 C18 C19 C20 169.9(4) . . . .
C17 C18 C19 C24 -6.7(5) . . . .
C24 C19 C20 C21 3.6(6) . . . .
C18 C19 C20 C21 -173.0(4) . . . .
C19 C20 C21 C22 1.1(6) . . . .
C20 C21 C22 C23 -4.2(6) . . . .
C21 C22 C23 C24 2.6(6) . . . .
C22 C23 C24 C19 2.0(5) . . . .
C22 C23 C24 C25 179.3(3) . . . .
C20 C19 C24 C23 -5.0(5) . . . .
C18 C19 C24 C23 171.7(3) . . . .
C20 C19 C24 C25 177.6(3) . . . .
C18 C19 C24 C25 -5.8(5) . . . .
C15 C16 C25 C26 -15.0(5) . . . .
C17 C16 C25 C26 166.5(3) . . . .
C15 C16 C25 C24 160.5(3) . . . .
C17 C16 C25 C24 -18.1(5) . . . .
C23 C24 C25 C16 -159.5(3) . . . .
C19 C24 C25 C16 17.8(5) . . . .
C23 C24 C25 C26 15.7(5) . . . .
C19 C24 C25 C26 -167.0(3) . . . .
C12 C13 C26 C25 165.3(3) . . . .
C14 C13 C26 C25 -16.0(5) . . . .
C12 C13 C26 C27 -17.7(5) . . . .
C14 C13 C26 C27 161.0(3) . . . .
C16 C25 C26 C13 24.3(4) . . . .
C24 C25 C26 C13 -150.8(3) . . . .
C16 C25 C26 C27 -152.4(3) . . . .
C24 C25 C26 C27 32.4(5) . . . .
C11 C10 C27 C28 165.8(3) . . . .
C9 C10 C27 C28 -11.9(5) . . . .
C11 C10 C27 C26 -7.2(5) . . . .
C9 C10 C27 C26 175.1(3) . . . .
C13 C26 C27 C10 19.2(5) . . . .
C25 C26 C27 C10 -164.1(3) . . . .
C13 C26 C27 C28 -153.3(3) . . . .
C25 C26 C27 C28 23.4(5) . . . .
N6 C7 C28 C29 -5.8(5) . . . .
C8 C7 C28 C29 170.0(3) . . . .
N6 C7 C28 C27 179.8(3) . . . .
C8 C7 C28 C27 -4.5(5) . . . .
C10 C27 C28 C29 -161.9(3) . . . .
C26 C27 C28 C29 10.6(5) . . . .
C10 C27 C28 C7 11.9(5) . . . .
C26 C27 C28 C7 -175.5(3) . . . .
C7 C28 C29 C30 4.0(5) . . . .
C27 C28 C29 C30 178.1(3) . . . .
C28 C29 C30 C5 0.4(5) . . . .
N6 C5 C30 C29 -3.7(5) . . . .
C4 C5 C30 C29 179.8(3) . . . .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 -0.002 207 25 ' '
2 1.000 0.500 -0.006 207 25 ' '
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132599299
