#------------------------------------------------------------------------------
#$Date: 2022-05-05 23:37:56 +0300 (Thu, 05 May 2022) $
#$Revision: 274992 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/45/7244544.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_7244544
loop_
_publ_author_name
'Sengoden, Mani'
'Bhat, Gulzar A.'
'Darensbourg, Donald J.'
_publ_section_title
;
 Explorations into the sustainable synthesis of cyclic and polymeric
 carbonates and thiocarbonates from eugenol-derived monomers and their
 reactions with CO2, COS, or CS2
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              2535
_journal_page_last               2541
_journal_paper_doi               10.1039/D2GC00327A
_journal_volume                  24
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H20 O6'
_chemical_formula_sum            'C16 H20 O6'
_chemical_formula_weight         308.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc29yg7z
_audit_creation_date             2021-10-11
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_audit_update_record
;
2022-01-20 deposited with the CCDC.	2022-02-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.9210(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.8206(5)
_cell_length_b                   6.2424(3)
_cell_length_c                   12.0066(5)
_cell_measurement_reflns_used    9668
_cell_measurement_temperature    110.00
_cell_measurement_theta_max      70.135
_cell_measurement_theta_min      3.916
_cell_volume                     762.48(6)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      110.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Venture (PHOTON III)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19407
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.157
_diffrn_reflns_theta_min         3.916
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  0.5856
_exptl_absorpt_correction_T_min  0.4507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1077 before and 0.0562 after correction.
The Ratio of minimum to maximum transmission is 0.7696.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.508
_exptl_crystal_size_mid          0.262
_exptl_crystal_size_min          0.143
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.5(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2814
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0308
_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)+(0.0485P)²+0.1855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0802
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                2774
_reflns_number_total             2814
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2gc00327a2.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7244542--7244545.cif.'
_cod_database_code               7244544
_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.
;
_shelx_estimated_absorpt_t_max   0.887
_shelx_estimated_absorpt_t_min   0.669
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5(2)
 0.5(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C5(H5)
3.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C16(H16A,H16B,H16C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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
O5 O 0.45483(12) 0.3202(2) 0.73772(11) 0.0203(3) Uani 1 1 d . . . . .
O4 O 0.38969(13) 0.0514(2) 0.55775(12) 0.0231(3) Uani 1 1 d . . . . .
O6 O 0.36229(13) 0.0466(3) 0.80400(12) 0.0253(3) Uani 1 1 d . . . . .
O1 O 0.06774(14) 0.8123(3) 0.26255(12) 0.0266(3) Uani 1 1 d . . . . .
O2 O -0.06869(14) 0.8123(3) 0.07687(12) 0.0276(3) Uani 1 1 d . . . . .
O3 O 0.03158(19) 1.1164(3) 0.15698(14) 0.0386(4) Uani 1 1 d . . . . .
C3 C 0.30569(19) 0.2186(3) 0.54626(17) 0.0192(4) Uani 1 1 d . . . . .
C4 C 0.33724(18) 0.3575(3) 0.64380(16) 0.0196(4) Uani 1 1 d . . . . .
C1 C 0.11796(18) 0.4421(3) 0.44639(17) 0.0198(4) Uani 1 1 d . . . . .
C2 C 0.19525(19) 0.2620(3) 0.44805(17) 0.0200(4) Uani 1 1 d . . . . .
H2 H 0.172152 0.168592 0.381627 0.024 Uiso 1 1 calc R U . . .
C12 C 0.45926(19) 0.1414(3) 0.80545(16) 0.0197(4) Uani 1 1 d . . . . .
C9 C 0.0116(2) 0.9300(4) 0.16504(18) 0.0238(4) Uani 1 1 d . . . . .
C7 C -0.00125(19) 0.4875(3) 0.33745(17) 0.0225(4) Uani 1 1 d . . . . .
H7A H -0.049108 0.351786 0.309389 0.027 Uiso 1 1 calc R U . . .
H7B H -0.061084 0.585443 0.359496 0.027 Uiso 1 1 calc R U . . .
C10 C -0.0789(2) 0.5985(4) 0.11969(17) 0.0243(4) Uani 1 1 d . . . . .
H10A H -0.069337 0.488696 0.063698 0.029 Uiso 1 1 calc R U . . .
H10B H -0.164418 0.577865 0.131379 0.029 Uiso 1 1 calc R U . . .
C13 C 0.60017(19) 0.0771(3) 0.87681(17) 0.0223(4) Uani 1 1 d . . . . .
C8 C 0.03450(18) 0.5869(3) 0.23733(17) 0.0200(4) Uani 1 1 d . . . . .
H8 H 0.110399 0.508654 0.226806 0.024 Uiso 1 1 calc R U . . .
C11 C 0.3723(2) -0.0764(4) 0.45439(19) 0.0262(4) Uani 1 1 d . . . . .
H11A H 0.377041 0.015362 0.389760 0.039 Uiso 1 1 calc R U . . .
H11B H 0.286230 -0.146866 0.430659 0.039 Uiso 1 1 calc R U . . .
H11C H 0.441592 -0.185196 0.472043 0.039 Uiso 1 1 calc R U . . .
C6 C 0.1523(2) 0.5785(4) 0.54321(17) 0.0242(4) Uani 1 1 d . . . . .
H6 H 0.100292 0.701701 0.542003 0.029 Uiso 1 1 calc R U . . .
C5 C 0.2631(2) 0.5362(4) 0.64276(17) 0.0240(4) Uani 1 1 d . . . . .
H5 H 0.286616 0.630191 0.708926 0.029 Uiso 1 1 calc R U . . .
C16 C 0.6991(2) 0.2566(4) 0.8895(2) 0.0310(5) Uani 1 1 d . . . . .
H16A H 0.700282 0.297050 0.810993 0.047 Uiso 1 1 calc R U . . .
H16B H 0.786709 0.207469 0.938695 0.047 Uiso 1 1 calc R U . . .
H16C H 0.673981 0.380807 0.926904 0.047 Uiso 1 1 calc R U . . .
C14 C 0.6316(2) -0.1116(4) 0.8091(2) 0.0377(6) Uani 1 1 d . . . . .
H14A H 0.568018 -0.227015 0.802198 0.057 Uiso 1 1 calc R U . . .
H14B H 0.720487 -0.164188 0.852084 0.057 Uiso 1 1 calc R U . . .
H14C H 0.626446 -0.064252 0.729842 0.057 Uiso 1 1 calc R U . . .
C15 C 0.6059(3) 0.0040(6) 1.0002(2) 0.0472(8) Uani 1 1 d . . . . .
H15A H 0.592408 0.127499 1.045157 0.071 Uiso 1 1 calc R U . . .
H15B H 0.692023 -0.059950 1.041926 0.071 Uiso 1 1 calc R U . . .
H15C H 0.536903 -0.102459 0.992622 0.071 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'
O O 0.0492 0.0322 '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
C12 O5 C4 116.77(15) . . ?
C3 O4 C11 116.96(15) . . ?
C9 O1 C8 109.97(15) . . ?
C9 O2 C10 109.46(15) . . ?
O4 C3 C4 115.20(17) . . ?
O4 C3 C2 125.99(17) . . ?
C2 C3 C4 118.81(18) . . ?
O5 C4 C3 117.68(17) . . ?
C5 C4 O5 120.67(17) . . ?
C5 C4 C3 121.33(17) . . ?
C2 C1 C7 119.41(18) . . ?
C6 C1 C2 119.63(18) . . ?
C6 C1 C7 120.95(18) . . ?
C3 C2 C1 120.42(17) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
O5 C12 C13 111.90(16) . . ?
O6 C12 O5 122.61(17) . . ?
O6 C12 C13 125.45(18) . . ?
O2 C9 O1 111.65(18) . . ?
O3 C9 O1 124.4(2) . . ?
O3 C9 O2 123.9(2) . . ?
C1 C7 H7A 109.0 . . ?
C1 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C1 112.84(16) . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
O2 C10 H10A 111.0 . . ?
O2 C10 H10B 111.0 . . ?
O2 C10 C8 103.74(15) . . ?
H10A C10 H10B 109.0 . . ?
C8 C10 H10A 111.0 . . ?
C8 C10 H10B 111.0 . . ?
C12 C13 C14 105.31(17) . . ?
C12 C13 C15 108.96(17) . . ?
C16 C13 C12 113.38(17) . . ?
C16 C13 C14 110.07(19) . . ?
C16 C13 C15 109.1(2) . . ?
C15 C13 C14 109.9(2) . . ?
O1 C8 C7 110.01(16) . . ?
O1 C8 C10 102.15(15) . . ?
O1 C8 H8 110.0 . . ?
C7 C8 C10 114.30(16) . . ?
C7 C8 H8 110.0 . . ?
C10 C8 H8 110.0 . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C6 H6 119.8 . . ?
C1 C6 C5 120.47(19) . . ?
C5 C6 H6 119.8 . . ?
C4 C5 C6 119.31(18) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
O5 C4 1.402(2) . ?
O5 C12 1.372(2) . ?
O4 C3 1.360(2) . ?
O4 C11 1.433(2) . ?
O6 C12 1.200(3) . ?
O1 C9 1.340(2) . ?
O1 C8 1.458(3) . ?
O2 C9 1.337(3) . ?
O2 C10 1.448(3) . ?
O3 C9 1.194(3) . ?
C3 C4 1.403(3) . ?
C3 C2 1.390(3) . ?
C4 C5 1.372(3) . ?
C1 C2 1.397(3) . ?
C1 C7 1.518(3) . ?
C1 C6 1.386(3) . ?
C2 H2 0.9500 . ?
C12 C13 1.526(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.516(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C8 1.525(3) . ?
C13 C16 1.521(3) . ?
C13 C14 1.534(3) . ?
C13 C15 1.532(3) . ?
C8 H8 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C6 H6 0.9500 . ?
C6 C5 1.399(3) . ?
C5 H5 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
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
_geom_torsion_publ_flag
O5 C4 C5 C6 174.54(18) . . . . ?
O5 C12 C13 C16 18.7(2) . . . . ?
O5 C12 C13 C14 -101.7(2) . . . . ?
O5 C12 C13 C15 140.4(2) . . . . ?
O4 C3 C4 O5 4.5(2) . . . . ?
O4 C3 C4 C5 178.08(18) . . . . ?
O4 C3 C2 C1 -178.77(18) . . . . ?
O6 C12 C13 C16 -163.5(2) . . . . ?
O6 C12 C13 C14 76.1(3) . . . . ?
O6 C12 C13 C15 -41.8(3) . . . . ?
O2 C10 C8 O1 16.84(18) . . . . ?
O2 C10 C8 C7 135.61(17) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C4 O5 C12 O6 -16.3(3) . . . . ?
C4 O5 C12 C13 161.61(16) . . . . ?
C4 C3 C2 C1 0.6(3) . . . . ?
C1 C7 C8 O1 -76.0(2) . . . . ?
C1 C7 C8 C10 169.74(17) . . . . ?
C1 C6 C5 C4 -0.2(3) . . . . ?
C2 C3 C4 O5 -174.91(16) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C2 C1 C7 C8 -78.3(2) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C12 O5 C4 C3 -70.2(2) . . . . ?
C12 O5 C4 C5 116.2(2) . . . . ?
C9 O1 C8 C7 -136.32(17) . . . . ?
C9 O1 C8 C10 -14.6(2) . . . . ?
C9 O2 C10 C8 -14.4(2) . . . . ?
C7 C1 C2 C3 179.26(17) . . . . ?
C7 C1 C6 C5 -179.44(19) . . . . ?
C10 O2 C9 O1 5.7(2) . . . . ?
C10 O2 C9 O3 -175.1(2) . . . . ?
C8 O1 C9 O2 6.3(2) . . . . ?
C8 O1 C9 O3 -172.9(2) . . . . ?
C11 O4 C3 C4 -171.27(17) . . . . ?
C11 O4 C3 C2 8.1(3) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
C6 C1 C7 C8 100.6(2) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5(2)
2 0.5(2)
