#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:01:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/86/2108608.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_2108608
loop_
_publ_author_name
'Vadra, Nahir'
'Suarez, Sebastian A.'
'Slep, Leonardo D.'
'Manzano, Veronica E.'
'Halac, Emilia B.'
'Baggio, Ricardo F.'
'Cukiernik, Fabio D.'
_publ_section_title
;
 Synthesis and crystallographic, spectroscopic and computational
 characterization of 3,3',4,4'-substituted biphenyls: effects of OR
 substituents on the intra-ring torsion angle
;
_journal_coeditor_code           LO5065SUP1
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520620004102
_journal_volume                  76
_journal_year                    2020
_chemical_formula_moiety         'C28 H38 O6'
_chemical_formula_sum            'C28 H38 O6'
_chemical_formula_weight         470.58
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                100.26(2)
_cell_angle_beta                 109.10(3)
_cell_angle_gamma                100.53(2)
_cell_formula_units_Z            1
_cell_length_a                   8.554(2)
_cell_length_b                   8.6844(17)
_cell_length_c                   9.810(3)
_cell_measurement_reflns_used    706
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.1980
_cell_measurement_theta_min      3.6600
_cell_volume                     654.5(3)
_computing_cell_refinement       'CrysAlisPro '
_computing_data_collection       'CrysAlisPro (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlisPro '
_computing_molecular_graphics    'SHELXTL   (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-2018, PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measurement_device_type  'Oxford Diffraction Gemini CCD S Ultra'
_diffrn_measurement_method       'ω scans, thick slices'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1462
_diffrn_reflns_av_unetI/netI     0.0862
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4799
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         28.974
_diffrn_reflns_theta_min         3.633
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, Oxford Diffraction (2009) '
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_description       fragment
_exptl_crystal_F_000             254
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2919
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.0693
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0729P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.1826
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1554
_reflns_number_total             2919
_reflns_threshold_expression     'I > 2σ(I)'
_publcif_datablock.id            {4dff3fc4-199a-4453-9811-844b2ffc230e}
_cod_data_source_file            lo5065sup1.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'direct methods' was
changed to 'direct'.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        654.4(3)
_cod_database_code               2108608
_cod_database_fobs_code          2108608
_shelx_shelxl_version_number     2018/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
O1 O 0.70994(19) 0.57970(17) 0.73363(17) 0.0500(5) Uani 1 1 d . . . . .
O2 O 0.5616(2) 0.78025(17) 0.86529(17) 0.0519(5) Uani 1 1 d . . . . .
O3 O 0.3331(2) 0.5636(2) 0.7495(2) 0.0625(5) Uani 1 1 d . . . . .
C1 C 0.6055(3) 0.8298(2) 0.4675(3) 0.0493(6) Uani 1 1 d . . . . .
H1A H 0.615786 0.839868 0.375759 0.059 Uiso 1 1 calc R U . . .
C2 C 0.6652(3) 0.7110(3) 0.5291(3) 0.0500(6) Uani 1 1 d . . . . .
H2A H 0.716344 0.643038 0.480093 0.060 Uiso 1 1 calc R U . . .
C3 C 0.6512(3) 0.6900(3) 0.6611(3) 0.0441(6) Uani 1 1 d . . . . .
C4 C 0.5718(3) 0.7916(3) 0.7265(3) 0.0428(6) Uani 1 1 d . . . . .
C5 C 0.5139(3) 0.9086(3) 0.6652(3) 0.0453(6) Uani 1 1 d . . . . .
H5A H 0.459982 0.974163 0.713264 0.054 Uiso 1 1 calc R U . . .
C6 C 0.5308(3) 0.9361(2) 0.5333(3) 0.0415(5) Uani 1 1 d . . . . .
C7 C 0.7953(3) 0.4775(3) 0.6664(3) 0.0479(6) Uani 1 1 d . . . . .
H7A H 0.895059 0.545241 0.655960 0.058 Uiso 1 1 calc R U . . .
H7B H 0.715571 0.411779 0.565905 0.058 Uiso 1 1 calc R U . . .
C8 C 0.8530(3) 0.3692(3) 0.7643(3) 0.0496(6) Uani 1 1 d . . . . .
H8A H 0.752030 0.303283 0.774489 0.060 Uiso 1 1 calc R U . . .
H8B H 0.930365 0.436713 0.864875 0.060 Uiso 1 1 calc R U . . .
C9 C 0.9458(3) 0.2565(3) 0.7048(3) 0.0489(6) Uani 1 1 d . . . . .
H9A H 0.870233 0.192240 0.602490 0.059 Uiso 1 1 calc R U . . .
H9B H 1.049443 0.322470 0.698516 0.059 Uiso 1 1 calc R U . . .
C10 C 0.9983(3) 0.1416(3) 0.8006(3) 0.0497(6) Uani 1 1 d . . . . .
H10A H 1.079320 0.206224 0.901028 0.060 Uiso 1 1 calc R U . . .
H10B H 0.895489 0.081116 0.812170 0.060 Uiso 1 1 calc R U . . .
C11 C 1.0812(3) 0.0213(3) 0.7385(3) 0.0601(7) Uani 1 1 d . . . . .
H11A H 1.002203 -0.040478 0.636505 0.072 Uiso 1 1 calc R U . . .
H11B H 1.186836 0.081545 0.730988 0.072 Uiso 1 1 calc R U . . .
C12 C 1.1264(3) -0.0968(3) 0.8322(3) 0.0668(8) Uani 1 1 d . . . . .
H12A H 1.179948 -0.171670 0.785776 0.100 Uiso 1 1 d R U . . .
H12B H 1.207678 -0.036300 0.933906 0.100 Uiso 1 1 d R U . . .
H12C H 1.021008 -0.159660 0.838196 0.100 Uiso 1 1 d R U . . .
C13 C 0.4325(4) 0.6594(3) 0.8625(3) 0.0539(7) Uani 1 1 d . . . . .
C14 C 0.4350(4) 0.6716(3) 1.0175(3) 0.0681(8) Uani 1 1 d . . . . .
H14A H 0.342355 0.584833 1.015274 0.102 Uiso 1 1 d R U . . .
H14B H 0.545305 0.660803 1.081744 0.102 Uiso 1 1 d R U . . .
H14C H 0.418795 0.776913 1.056754 0.102 Uiso 1 1 d 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 0.0033 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C7 116.94(17) . . ?
C13 O2 C4 116.82(19) . . ?
C2 C1 C6 123.3(2) . . ?
C2 C1 H1A 118.4 . . ?
C6 C1 H1A 118.4 . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
O1 C3 C2 125.46(19) . . ?
O1 C3 C4 117.5(2) . . ?
C2 C3 C4 117.1(2) . . ?
C5 C4 C3 121.8(2) . . ?
C5 C4 O2 118.71(19) . . ?
C3 C4 O2 119.31(19) . . ?
C4 C5 C6 122.4(2) . . ?
C4 C5 H5A 118.8 . . ?
C6 C5 H5A 118.8 . . ?
C1 C6 C5 114.7(2) . . ?
C1 C6 C6 122.6(3) . 2_676 ?
C5 C6 C6 122.7(2) . 2_676 ?
O1 C7 C8 108.50(18) . . ?
O1 C7 H7A 110.0 . . ?
C8 C7 H7A 110.0 . . ?
O1 C7 H7B 110.0 . . ?
C8 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
C7 C8 C9 113.11(19) . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 113.2(2) . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 114.2(2) . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C10 113.6(2) . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.4 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 O2 122.9(2) . . ?
O3 C13 C14 127.5(2) . . ?
O2 C13 C14 109.5(2) . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.364(3) . ?
O1 C7 1.448(2) . ?
O2 C13 1.367(3) . ?
O2 C4 1.412(2) . ?
O3 C13 1.200(3) . ?
C1 C2 1.379(3) . ?
C1 C6 1.397(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.379(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.398(3) . ?
C4 C5 1.359(3) . ?
C5 C6 1.404(3) . ?
C5 H5A 0.9500 . ?
C6 C6 1.477(4) 2_676 ?
C7 C8 1.494(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.520(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.517(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.514(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.515(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9901 . ?
C12 H12B 0.9900 . ?
C12 H12C 0.9900 . ?
C13 C14 1.498(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2A O3 0.95 2.48 3.298(3) 144.7 2_666 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168308501
