#------------------------------------------------------------------------------
#$Date: 2024-02-04 13:10:16 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289347 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/24/7132414.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_7132414
loop_
_publ_author_name
'Garbini, Mauro'
'Brunetti, Andrea'
'Pedrazzani, Riccardo'
'Monari, Magda'
'Marcaccio, Massimo'
'Bertuzzi, Giulio'
'Bandini, Marco'
_publ_section_title
;
 Reductive cyclodimerization of chalcones: exploring the
 "self-adaptability" of galvanostatic electrosynthesis.
;
_journal_issue                   4
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              404
_journal_page_last               407
_journal_paper_doi               10.1039/d3cc04920e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_sum            'C33 H34 O3'
_chemical_formula_weight         478.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-08-23 deposited with the CCDC.	2023-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.709(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.7540(16)
_cell_length_b                   5.9450(5)
_cell_length_c                   24.1084(19)
_cell_measurement_reflns_used    7426
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.56
_cell_measurement_theta_min      2.53
_cell_volume                     2744.0(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0631
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            31699
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.534
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7488
_exptl_absorpt_correction_T_min  0.6932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_description       needle
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4793
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0982
_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)+(0.0795P)²+3.5909P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2160
_refine_ls_wR_factor_ref         0.2272
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3894
_reflns_number_total             4793
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc04920e2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7132413--7132414.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7132414
_shelx_shelxl_version_number     2018/3
_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.48571(13) 0.3105(4) 0.80918(10) 0.0425(6) Uani 1 1 d . . . . .
H1A H 0.503550 0.292540 0.845713 0.064 Uiso 1 1 calc R U . . .
O2 O 0.41246(15) 0.1854(4) 0.69455(12) 0.0518(7) Uani 1 1 d . . . . .
H2A H 0.439816 0.163634 0.729256 0.078 Uiso 1 1 calc R U . . .
C19 C 0.52641(14) 0.6229(5) 0.66817(14) 0.0310(7) Uani 1 1 d . . . . .
C2 C 0.44637(15) 0.5714(5) 0.72840(13) 0.0289(7) Uani 1 1 d . . . . .
H2 H 0.428918 0.725118 0.717780 0.035 Uiso 1 1 calc R U . . .
C3 C 0.51972(15) 0.5617(5) 0.72650(13) 0.0303(7) Uani 1 1 d . . . . .
H3 H 0.537411 0.408140 0.736929 0.036 Uiso 1 1 calc R U . . .
C7 C 0.40020(17) 0.5837(6) 0.81296(14) 0.0354(7) Uani 1 1 d . . . . .
C6 C 0.38985(16) 0.4118(5) 0.68800(15) 0.0355(7) Uani 1 1 d . . . . .
H6 H 0.350822 0.419659 0.701268 0.043 Uiso 1 1 calc R U . . .
C13 C 0.36109(15) 0.4755(6) 0.62213(15) 0.0371(8) Uani 1 1 d . . . . .
C1 C 0.46294(16) 0.5404(5) 0.79606(14) 0.0346(7) Uani 1 1 d . . . . .
C4 C 0.56233(16) 0.7171(6) 0.78008(15) 0.0373(8) Uani 1 1 d . . . . .
H4 H 0.555789 0.872044 0.765056 0.045 Uiso 1 1 calc R U . . .
C20 C 0.50408(19) 0.8261(6) 0.64004(16) 0.0469(9) Uani 1 1 d . . . . .
H20 H 0.483802 0.930845 0.656999 0.056 Uiso 1 1 calc R U . . .
C24 C 0.55691(18) 0.4723(6) 0.64190(16) 0.0450(9) Uani 1 1 d . . . . .
H24 H 0.572481 0.334022 0.660230 0.054 Uiso 1 1 calc R U . . .
C25 C 0.63955(17) 0.6682(6) 0.80408(14) 0.0412(8) Uani 1 1 d . . . . .
C5 C 0.52548(18) 0.6962(6) 0.82555(15) 0.0419(8) Uani 1 1 d . . . . .
H5A H 0.557233 0.633181 0.863333 0.050 Uiso 1 1 calc R U . . .
H5B H 0.510108 0.842616 0.833310 0.050 Uiso 1 1 calc R U . . .
C12 C 0.3638(2) 0.7829(6) 0.79855(18) 0.0502(10) Uani 1 1 d . . . . .
H12 H 0.379406 0.896541 0.780332 0.060 Uiso 1 1 calc R U . . .
C8 C 0.37524(19) 0.4188(7) 0.84015(17) 0.0491(9) Uani 1 1 d . . . . .
H8 H 0.398430 0.281654 0.850281 0.059 Uiso 1 1 calc R U . . .
C18 C 0.3647(2) 0.3318(8) 0.57888(17) 0.0554(10) Uani 1 1 d . . . . .
H18 H 0.385547 0.191464 0.589851 0.067 Uiso 1 1 calc R U . . .
C14 C 0.3283(2) 0.6808(7) 0.60350(19) 0.0592(11) Uani 1 1 d . . . . .
H14 H 0.324230 0.779114 0.631962 0.071 Uiso 1 1 calc R U . . .
C21 C 0.5114(2) 0.8762(7) 0.58698(18) 0.0579(11) Uani 1 1 d . . . . .
H21 H 0.495730 1.013714 0.568263 0.069 Uiso 1 1 calc R U . . .
C22 C 0.5418(2) 0.7244(8) 0.56156(17) 0.0614(12) Uani 1 1 d . . . . .
H22 H 0.546651 0.758861 0.525758 0.074 Uiso 1 1 calc R U . . .
C10 C 0.2808(2) 0.6537(8) 0.83755(19) 0.0607(11) Uani 1 1 d . . . . .
H10 H 0.241020 0.676866 0.845677 0.073 Uiso 1 1 calc R U . . .
C9 C 0.3163(2) 0.4556(8) 0.85239(19) 0.0611(11) Uani 1 1 d . . . . .
H9 H 0.300693 0.343482 0.871046 0.073 Uiso 1 1 calc R U . . .
C11 C 0.3047(2) 0.8184(7) 0.81043(19) 0.0589(11) Uani 1 1 d . . . . .
H11 H 0.280910 0.954487 0.800023 0.071 Uiso 1 1 calc R U . . .
C30 C 0.6673(2) 0.4698(8) 0.83353(19) 0.0606(11) Uani 1 1 d . . . . .
H30 H 0.638081 0.365844 0.840869 0.073 Uiso 1 1 calc R U . . .
C23 C 0.5646(2) 0.5234(8) 0.58902(18) 0.0623(12) Uani 1 1 d . . . . .
H23 H 0.585493 0.420313 0.572117 0.075 Uiso 1 1 calc R U . . .
C29 C 0.7378(2) 0.4232(9) 0.8523(2) 0.0746(14) Uani 1 1 d . . . . .
H29 H 0.755402 0.288212 0.871729 0.089 Uiso 1 1 calc R U . . .
C17 C 0.3374(3) 0.3953(10) 0.5188(2) 0.0787(15) Uani 1 1 d . . . . .
H17 H 0.340650 0.297189 0.489913 0.094 Uiso 1 1 calc R U . . .
C15 C 0.3019(3) 0.7423(9) 0.5443(2) 0.0819(15) Uani 1 1 d . . . . .
H15 H 0.280995 0.882372 0.533045 0.098 Uiso 1 1 calc R U . . .
C16 C 0.3062(3) 0.5976(11) 0.5016(2) 0.0853(16) Uani 1 1 d . . . . .
H16 H 0.287779 0.638064 0.461191 0.102 Uiso 1 1 calc R U . . .
C28 C 0.7817(2) 0.5736(11) 0.8424(2) 0.0803(16) Uani 1 1 d . . . . .
H28 H 0.829173 0.542755 0.855483 0.096 Uiso 1 1 calc R U . . .
C27 C 0.7557(2) 0.7681(11) 0.8134(2) 0.0826(16) Uani 1 1 d . . . . .
H27 H 0.785432 0.870634 0.806319 0.099 Uiso 1 1 calc R U . . .
C26 C 0.6851(2) 0.8162(8) 0.7942(2) 0.0627(11) Uani 1 1 d . . . . .
H26 H 0.668146 0.950800 0.774263 0.075 Uiso 1 1 calc R U . . .
O1S O 0.5424(3) 0.1806(10) 0.92903(19) 0.142(2) Uani 1 1 d . . . . .
C2S C 0.5863(5) 0.1658(16) 0.9736(3) 0.135(3) Uani 1 1 d . . . . .
C1S C 0.6505(8) 0.268(4) 0.9851(7) 0.369(13) Uani 1 1 d . . . . .
H1S1 H 0.681600 0.236344 1.025681 0.554 Uiso 1 1 calc R U . . .
H1S2 H 0.670071 0.209481 0.957813 0.554 Uiso 1 1 calc R U . . .
H1S3 H 0.644206 0.427200 0.979616 0.554 Uiso 1 1 calc R U . . .
C3S C 0.6020(8) 0.002(3) 1.0198(6) 0.347(12) Uani 1 1 d . . . . .
H3S1 H 0.644502 0.042741 1.052540 0.520 Uiso 0.5 1 calc R U P . .
H3S2 H 0.564546 -0.004394 1.033815 0.520 Uiso 0.5 1 calc R U P . .
H3S3 H 0.607492 -0.142052 1.004350 0.520 Uiso 0.5 1 calc R U P . .
H3S4 H 0.566524 -0.111878 1.007930 0.520 Uiso 0.5 1 calc R U P . .
H3S5 H 0.646481 -0.064742 1.026655 0.520 Uiso 0.5 1 calc R U P . .
H3S6 H 0.603535 0.072915 1.056120 0.520 Uiso 0.5 1 calc R U P . .
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
C1 O1 H1A 109.5 . . ?
C6 O2 H2A 109.5 . . ?
C20 C19 C24 118.0(3) . . ?
C20 C19 C3 122.4(3) . . ?
C24 C19 C3 119.6(3) . . ?
C6 C2 C3 118.7(2) . . ?
C6 C2 C1 113.7(2) . . ?
C3 C2 C1 102.0(2) . . ?
C6 C2 H2 107.3 . . ?
C3 C2 H2 107.3 . . ?
C1 C2 H2 107.3 . . ?
C19 C3 C2 117.7(2) . . ?
C19 C3 C4 113.8(3) . . ?
C2 C3 C4 101.8(2) . . ?
C19 C3 H3 107.7 . . ?
C2 C3 H3 107.7 . . ?
C4 C3 H3 107.7 . . ?
C12 C7 C8 117.3(3) . . ?
C12 C7 C1 121.3(3) . . ?
C8 C7 C1 121.3(3) . . ?
O2 C6 C13 109.6(3) . . ?
O2 C6 C2 112.3(3) . . ?
C13 C6 C2 114.0(3) . . ?
O2 C6 H6 106.8 . . ?
C13 C6 H6 106.8 . . ?
C2 C6 H6 106.8 . . ?
C18 C13 C14 117.8(4) . . ?
C18 C13 C6 121.8(3) . . ?
C14 C13 C6 120.4(3) . . ?
O1 C1 C5 109.0(3) . . ?
O1 C1 C7 110.0(3) . . ?
C5 C1 C7 115.6(3) . . ?
O1 C1 C2 105.4(2) . . ?
C5 C1 C2 102.8(2) . . ?
C7 C1 C2 113.4(3) . . ?
C25 C4 C3 112.6(3) . . ?
C25 C4 C5 116.8(3) . . ?
C3 C4 C5 105.0(2) . . ?
C25 C4 H4 107.3 . . ?
C3 C4 H4 107.3 . . ?
C5 C4 H4 107.3 . . ?
C19 C20 C21 120.7(3) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C23 C24 C19 121.2(4) . . ?
C23 C24 H24 119.4 . . ?
C19 C24 H24 119.4 . . ?
C26 C25 C30 117.1(3) . . ?
C26 C25 C4 120.6(3) . . ?
C30 C25 C4 122.2(3) . . ?
C1 C5 C4 106.2(3) . . ?
C1 C5 H5A 110.5 . . ?
C4 C5 H5A 110.5 . . ?
C1 C5 H5B 110.5 . . ?
C4 C5 H5B 110.5 . . ?
H5A C5 H5B 108.7 . . ?
C7 C12 C11 121.7(3) . . ?
C7 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C9 C8 C7 120.8(4) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C13 C18 C17 120.3(4) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C15 C14 C13 121.6(4) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C22 C21 C20 120.4(4) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C21 119.6(4) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C9 C10 C11 119.0(3) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C10 C9 C8 121.0(4) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C10 C11 C12 120.2(4) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C29 C30 C25 121.2(4) . . ?
C29 C30 H30 119.4 . . ?
C25 C30 H30 119.4 . . ?
C22 C23 C24 120.0(4) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C28 C29 C30 120.4(5) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C16 C17 C18 121.0(5) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C14 C15 C16 120.0(5) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 119.3(5) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C27 C28 C29 119.5(4) . . ?
C27 C28 H28 120.3 . . ?
C29 C28 H28 120.3 . . ?
C28 C27 C26 120.7(5) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C25 C26 C27 121.2(5) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
O1S C2S C1S 121.4(10) . . ?
O1S C2S C3S 131.9(10) . . ?
C1S C2S C3S 103.3(10) . . ?
C2S C1S H1S1 109.5 . . ?
C2S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
C2S C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
C2S C3S H3S1 109.5 . . ?
C2S C3S H3S2 109.5 . . ?
H3S1 C3S H3S2 109.5 . . ?
C2S C3S H3S3 109.5 . . ?
H3S1 C3S H3S3 109.5 . . ?
H3S2 C3S H3S3 109.5 . . ?
H3S4 C3S H3S5 109.5 . . ?
H3S4 C3S H3S6 109.5 . . ?
H3S5 C3S H3S6 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 C1 1.441(4) . ?
O1 H1A 0.8200 . ?
O2 C6 1.414(4) . ?
O2 H2A 0.8200 . ?
C19 C20 1.375(5) . ?
C19 C24 1.383(4) . ?
C19 C3 1.510(4) . ?
C2 C6 1.531(4) . ?
C2 C3 1.542(4) . ?
C2 C1 1.543(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.556(4) . ?
C3 H3 0.9800 . ?
C7 C12 1.375(5) . ?
C7 C8 1.386(5) . ?
C7 C1 1.529(4) . ?
C6 C13 1.513(5) . ?
C6 H6 0.9800 . ?
C13 C18 1.372(5) . ?
C13 C14 1.385(5) . ?
C1 C5 1.528(5) . ?
C4 C25 1.507(5) . ?
C4 C5 1.565(5) . ?
C4 H4 0.9800 . ?
C20 C21 1.378(5) . ?
C20 H20 0.9300 . ?
C24 C23 1.379(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.377(5) . ?
C25 C30 1.383(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C12 C11 1.379(5) . ?
C12 H12 0.9300 . ?
C8 C9 1.381(5) . ?
C8 H8 0.9300 . ?
C18 C17 1.389(6) . ?
C18 H18 0.9300 . ?
C14 C15 1.365(6) . ?
C14 H14 0.9300 . ?
C21 C22 1.372(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.360(6) . ?
C22 H22 0.9300 . ?
C10 C9 1.361(6) . ?
C10 C11 1.372(6) . ?
C10 H10 0.9300 . ?
C9 H9 0.9300 . ?
C11 H11 0.9300 . ?
C30 C29 1.382(6) . ?
C30 H30 0.9300 . ?
C23 H23 0.9300 . ?
C29 C28 1.360(7) . ?
C29 H29 0.9300 . ?
C17 C16 1.353(8) . ?
C17 H17 0.9300 . ?
C15 C16 1.372(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C28 C27 1.351(8) . ?
C28 H28 0.9300 . ?
C27 C26 1.385(6) . ?
C27 H27 0.9300 . ?
C26 H26 0.9300 . ?
O1S C2S 1.112(7) . ?
C2S C1S 1.391(17) . ?
C2S C3S 1.418(12) . ?
C1S H1S1 0.9600 . ?
C1S H1S2 0.9600 . ?
C1S H1S3 0.9600 . ?
C3S H3S1 0.9600 . ?
C3S H3S2 0.9600 . ?
C3S H3S3 0.9600 . ?
C3S H3S4 0.9600 . ?
C3S H3S5 0.9600 . ?
C3S H3S6 0.9600 . ?
