#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:01:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/86/2108607.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_2108607
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         'C36 H58 O4'
_chemical_formula_sum            'C36 H58 O4'
_chemical_formula_weight         554.82
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2019-11-19 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 96.221(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   22.486(2)
_cell_length_b                   8.8585(9)
_cell_length_c                   8.3874(8)
_cell_measurement_reflns_used    8395
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.19
_cell_measurement_theta_min      2.47
_cell_volume                     1660.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL   (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-2018, PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2018 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0836
_diffrn_reflns_av_unetI/netI     0.0694
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            26569
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.599
_diffrn_reflns_theta_min         2.473
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SAINT'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.109
_exptl_crystal_description       fragment
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.254
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         4907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.254
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0685
_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)+(0.0362P)²+0.4066P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1330
_refine_ls_wR_factor_ref         0.1432
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3347
_reflns_number_total             4907
_reflns_threshold_expression     'I > 2σ(I)'
_publcif_datablock.id            {47ede442-4831-4e11-8b32-c25b40e29279}
_cod_data_source_file            lo5065sup1.cif
_cod_data_source_block           I
_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        1660.8(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2108607
_cod_database_fobs_code          2108607
_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.62808(4) 0.53454(12) 0.56014(11) 0.0255(3) Uani 1 1 d . . . . .
O2 O 0.66405(4) 0.37790(12) 0.81108(11) 0.0271(3) Uani 1 1 d . . . . .
C1 C 0.50070(6) 0.59344(17) 0.79638(16) 0.0235(3) Uani 1 1 d . . . . .
H1A H 0.463691 0.646004 0.790133 0.028 Uiso 1 1 calc R U . . .
C2 C 0.53584(6) 0.60466(17) 0.66974(16) 0.0233(3) Uani 1 1 d . . . . .
H2A H 0.522363 0.663905 0.578510 0.028 Uiso 1 1 calc R U . . .
C3 C 0.58986(6) 0.53073(16) 0.67563(15) 0.0202(3) Uani 1 1 d . . . . .
C4 C 0.60933(6) 0.44426(16) 0.81256(16) 0.0206(3) Uani 1 1 d . . . . .
C5 C 0.57385(6) 0.43294(16) 0.93620(16) 0.0214(3) Uani 1 1 d . . . . .
H5A H 0.587275 0.373179 1.027070 0.026 Uiso 1 1 calc R U . . .
C6 C 0.51860(6) 0.50686(16) 0.93197(15) 0.0191(3) Uani 1 1 d . . . . .
C7 C 0.61685(6) 0.64258(17) 0.43261(16) 0.0240(3) Uani 1 1 d . . . . .
H7A H 0.612290 0.745040 0.476845 0.029 Uiso 1 1 calc R U . . .
H7B H 0.579765 0.616410 0.363526 0.029 Uiso 1 1 calc R U . . .
C8 C 0.67018(7) 0.63693(19) 0.33730(16) 0.0268(3) Uani 1 1 d . . . . .
H8A H 0.664135 0.710594 0.248258 0.032 Uiso 1 1 calc R U . . .
H8B H 0.672609 0.535146 0.289684 0.032 Uiso 1 1 calc R U . . .
C9 C 0.72899(7) 0.67160(19) 0.43771(17) 0.0286(3) Uani 1 1 d . . . . .
H9A H 0.733554 0.602253 0.530794 0.034 Uiso 1 1 calc R U . . .
H9B H 0.727322 0.775802 0.479661 0.034 Uiso 1 1 calc R U . . .
C10 C 0.78390(7) 0.6569(2) 0.34676(18) 0.0305(4) Uani 1 1 d . . . . .
H10A H 0.780598 0.562808 0.282761 0.037 Uiso 1 1 calc R U . . .
H10B H 0.784702 0.742704 0.271369 0.037 Uiso 1 1 calc R U . . .
C11 C 0.84186(7) 0.6543(2) 0.4562(2) 0.0417(4) Uani 1 1 d . . . . .
H11A H 0.839488 0.573880 0.537245 0.050 Uiso 1 1 calc R U . . .
H11B H 0.846450 0.751823 0.513919 0.050 Uiso 1 1 calc R U . . .
C12 C 0.89717(8) 0.6275(3) 0.3699(2) 0.0491(5) Uani 1 1 d . . . . .
H12A H 0.932599 0.621468 0.448711 0.074 Uiso 1 1 calc R U . . .
H12B H 0.901868 0.711043 0.295708 0.074 Uiso 1 1 calc R U . . .
H12C H 0.892598 0.532577 0.309666 0.074 Uiso 1 1 calc R U . . .
C13 C 0.68889(7) 0.30644(19) 0.95673(17) 0.0271(3) Uani 1 1 d . . . . .
H13A H 0.663522 0.220440 0.982681 0.032 Uiso 1 1 calc R U . . .
H13B H 0.691264 0.379189 1.046794 0.032 Uiso 1 1 calc R U . . .
C14 C 0.75054(7) 0.25185(19) 0.93039(18) 0.0297(4) Uani 1 1 d . . . . .
H14A H 0.747335 0.188915 0.832296 0.036 Uiso 1 1 calc R U . . .
H14B H 0.765587 0.186434 1.021653 0.036 Uiso 1 1 calc R U . . .
C15 C 0.79601(7) 0.3752(2) 0.91342(19) 0.0323(4) Uani 1 1 d . . . . .
H15A H 0.801348 0.435073 1.013610 0.039 Uiso 1 1 calc R U . . .
H15B H 0.780646 0.443657 0.825147 0.039 Uiso 1 1 calc R U . . .
C16 C 0.85627(7) 0.3125(2) 0.8791(2) 0.0383(4) Uani 1 1 d . . . . .
H16A H 0.869997 0.238658 0.963735 0.046 Uiso 1 1 calc R U . . .
H16B H 0.850988 0.257684 0.775665 0.046 Uiso 1 1 calc R U . . .
C17 C 0.90438(8) 0.4308(3) 0.8712(2) 0.0518(5) Uani 1 1 d . . . . .
H17A H 0.911482 0.481910 0.976531 0.062 Uiso 1 1 calc R U . . .
H17B H 0.890033 0.507698 0.790418 0.062 Uiso 1 1 calc R U . . .
C18 C 0.96299(9) 0.3659(4) 0.8282(3) 0.0780(8) Uani 1 1 d . . . . .
H18A H 0.991880 0.447818 0.820919 0.117 Uiso 1 1 calc R U . . .
H18B H 0.956223 0.313838 0.724760 0.117 Uiso 1 1 calc R U . . .
H18C H 0.978748 0.294190 0.911253 0.117 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 0.0033 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 118.15(11) . . ?
C4 O2 C13 116.79(10) . . ?
C2 C1 C6 121.54(13) . . ?
C2 C1 H1A 119.2 . . ?
C6 C1 H1A 119.2 . . ?
C3 C2 C1 120.64(13) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
O1 C3 C2 125.78(12) . . ?
O1 C3 C4 115.36(12) . . ?
C2 C3 C4 118.86(12) . . ?
O2 C4 C5 124.83(12) . . ?
O2 C4 C3 115.28(11) . . ?
C5 C4 C3 119.88(13) . . ?
C4 C5 C6 122.04(13) . . ?
C4 C5 H5A 119.0 . . ?
C6 C5 H5A 119.0 . . ?
C1 C6 C5 117.03(12) . . ?
C1 C6 C6 122.18(15) . 3_667 ?
C5 C6 C6 120.79(15) . 3_667 ?
O1 C7 C8 106.61(11) . . ?
O1 C7 H7A 110.4 . . ?
C8 C7 H7A 110.4 . . ?
O1 C7 H7B 110.4 . . ?
C8 C7 H7B 110.4 . . ?
H7A C7 H7B 108.6 . . ?
C7 C8 C9 113.11(11) . . ?
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 . . ?
C8 C9 C10 114.10(12) . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
C10 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C9 112.89(12) . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C12 114.09(14) . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 C14 107.24(11) . . ?
O2 C13 H13A 110.3 . . ?
C14 C13 H13A 110.3 . . ?
O2 C13 H13B 110.3 . . ?
C14 C13 H13B 110.3 . . ?
H13A C13 H13B 108.5 . . ?
C13 C14 C15 115.07(14) . . ?
C13 C14 H14A 108.5 . . ?
C15 C14 H14A 108.5 . . ?
C13 C14 H14B 108.5 . . ?
C15 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C14 C15 C16 112.29(15) . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C15 114.31(17) . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C15 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C16 C17 C18 113.1(2) . . ?
C16 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 1.3633(16) . ?
O1 C7 1.4371(16) . ?
O2 C4 1.3649(17) . ?
O2 C13 1.4342(17) . ?
C1 C2 1.3945(19) . ?
C1 C6 1.3944(19) . ?
C1 H1A 0.9500 . ?
C2 C3 1.376(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.4101(19) . ?
C4 C5 1.3788(19) . ?
C5 C6 1.4013(19) . ?
C5 H5A 0.9500 . ?
C6 C6 1.491(3) 3_667 ?
C7 C8 1.5125(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.520(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.526(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.511(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.524(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9801 . ?
C12 H12B 0.9801 . ?
C12 H12C 0.9801 . ?
C13 C14 1.507(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.514(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.520(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.512(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.517(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9801 . ?
C18 H18B 0.9801 . ?
C18 H18C 0.9801 . ?
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
C13 H13A O1 0.99 2.50 3.4645(19) 163.4 4_566 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 14937397
