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#$Date: 2021-11-03 23:14:12 +0200 (Wed, 03 Nov 2021) $
#$Revision: 270246 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/91/4519106.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_4519106
loop_
_publ_author_name
'Liu, Kuan-Ting'
'Chuang, Jia-Yu'
'Jeng, Ru-Jong'
'Leung, Man-Kit'
_publ_section_title
;
 Sustainable Synthesis of Cyclic Carbonates from Terminal Epoxides by a
 Highly Efficient
 CaI₂/1,3-Bis[tris(hydroxymethyl)-methylamino]-propane
 Catalyst.
;
_journal_issue                   41
_journal_name_full               'ACS omega'
_journal_page_first              27279
_journal_page_last               27287
_journal_paper_doi               10.1021/acsomega.1c04086
_journal_volume                  6
_journal_year                    2021
_chemical_formula_sum            'C23 H24 O8'
_chemical_formula_weight         428.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 108.828(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   29.327(6)
_cell_length_b                   5.8690(9)
_cell_length_c                   12.6542(17)
_cell_measurement_reflns_used    2048
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.0650
_cell_measurement_theta_min      4.4530
_cell_volume                     2061.5(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.2496
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6489
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.879
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       plate
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.760
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         2300
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0742
_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)+(0.1061P)²+2.1205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1973
_refine_ls_wR_factor_ref         0.2140
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1809
_reflns_number_total             2300
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao1c04086_si_004.cif
_cod_data_source_block           ic20187
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4519106
_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, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.63883(7) 0.6720(3) 0.53861(14) 0.0471(5) Uani 1 1 d . . . . .
O2 O 0.67222(8) 1.0561(4) 0.7265(2) 0.0719(7) Uani 1 1 d . . . . .
O3 O 0.71560(9) 0.8423(4) 0.86693(19) 0.0705(7) Uani 1 1 d . . . . .
O4 O 0.72633(7) 0.8238(4) 0.70075(16) 0.0541(6) Uani 1 1 d . . . . .
C1 C 0.52225(14) -0.0858(5) 0.1818(3) 0.0686(10) Uani 1 1 d . . . . .
H1A H 0.546999 -0.182070 0.232782 0.103 Uiso 1 1 calc R U . . .
H1B H 0.496999 -0.182304 0.132420 0.103 Uiso 1 1 calc R U . . .
H1C H 0.536845 0.007008 0.136828 0.103 Uiso 1 1 calc R U . . .
C2 C 0.500000 0.0719(6) 0.250000 0.0478(9) Uani 1 2 d S T P . .
C3 C 0.53908(9) 0.2260(4) 0.3271(2) 0.0395(6) Uani 1 1 d . . . . .
C4 C 0.53493(10) 0.3089(5) 0.4264(2) 0.0480(7) Uani 1 1 d . . . . .
H4A H 0.508202 0.262620 0.448110 0.058 Uiso 1 1 calc R U . . .
C5 C 0.56825(9) 0.4560(5) 0.4947(2) 0.0470(7) Uani 1 1 d . . . . .
H5A H 0.564355 0.508418 0.562267 0.056 Uiso 1 1 calc R U . . .
C6 C 0.60709(9) 0.5269(4) 0.4649(2) 0.0398(6) Uani 1 1 d . . . . .
C7 C 0.61293(11) 0.4466(6) 0.3675(2) 0.0535(8) Uani 1 1 d . . . . .
H7A H 0.639800 0.493412 0.346531 0.064 Uiso 1 1 calc R U . . .
C8 C 0.57913(11) 0.2968(5) 0.3005(2) 0.0525(7) Uani 1 1 d . . . . .
H8A H 0.583656 0.240915 0.234100 0.063 Uiso 1 1 calc R U . . .
C9 C 0.67834(13) 0.7577(7) 0.5063(3) 0.0682(10) Uani 1 1 d . . . . .
H9A H 0.666218 0.828533 0.431389 0.082 Uiso 1 1 calc R U . . .
H9B H 0.700472 0.632082 0.503698 0.082 Uiso 1 1 calc R U . . .
C10 C 0.70428(15) 0.9322(6) 0.5920(3) 0.0717(11) Uani 1 1 d . . . . .
H10A H 0.729565 1.009955 0.567696 0.086 Uiso 1 1 calc R U . . .
C11 C 0.67134(14) 1.1073(6) 0.6170(4) 0.0872(14) Uani 1 1 d . . . . .
H11A H 0.683352 1.263585 0.612842 0.105 Uiso 1 1 calc R U . . .
H11B H 0.638247 1.094082 0.563734 0.105 Uiso 1 1 calc R U . . .
C12 C 0.70550(10) 0.9030(5) 0.7728(3) 0.0501(7) Uani 1 1 d . . . . .
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
C6 O1 C9 117.0(2) . . ?
C12 O2 C11 111.0(3) . . ?
C12 O4 C10 109.3(2) . . ?
C3 C2 C3 107.9(3) 2_655 . ?
C3 C2 C1 111.13(16) 2_655 . ?
C3 C2 C1 110.12(17) . . ?
C3 C2 C1 110.12(17) 2_655 2_655 ?
C3 C2 C1 111.14(16) . 2_655 ?
C1 C2 C1 106.5(4) . 2_655 ?
C8 C3 C4 116.3(2) . . ?
C8 C3 C2 122.6(2) . . ?
C4 C3 C2 121.0(2) . . ?
C5 C4 C3 122.3(3) . . ?
C6 C5 C4 120.0(2) . . ?
C5 C6 O1 116.1(2) . . ?
C5 C6 C7 119.6(2) . . ?
O1 C6 C7 124.3(2) . . ?
C6 C7 C8 119.4(3) . . ?
C3 C8 C7 122.3(3) . . ?
O1 C9 C10 107.4(3) . . ?
O4 C10 C9 110.4(3) . . ?
O4 C10 C11 102.5(3) . . ?
C9 C10 C11 113.8(3) . . ?
O2 C11 C10 104.5(3) . . ?
O3 C12 O2 124.1(3) . . ?
O3 C12 O4 124.1(3) . . ?
O2 C12 O4 111.7(3) . . ?
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 C6 1.379(3) . ?
O1 C9 1.438(4) . ?
O2 C12 1.317(4) . ?
O2 C11 1.410(5) . ?
O3 C12 1.185(4) . ?
O4 C12 1.335(3) . ?
O4 C10 1.464(4) . ?
C1 C2 1.546(4) . ?
C2 C3 1.537(3) 2_655 ?
C2 C3 1.537(3) . ?
C3 C8 1.386(4) . ?
C3 C4 1.390(4) . ?
C4 C5 1.379(4) . ?
C5 C6 1.374(4) . ?
C6 C7 1.380(4) . ?
C7 C8 1.390(4) . ?
C9 C10 1.507(5) . ?
C10 C11 1.513(6) . ?
