#------------------------------------------------------------------------------
#$Date: 2021-11-03 23:13:27 +0200 (Wed, 03 Nov 2021) $
#$Revision: 270244 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/91/4519104.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_4519104
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            'C19 H20 O4'
_chemical_formula_weight         312.35
_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   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                92.500(8)
_cell_angle_beta                 94.608(7)
_cell_angle_gamma                103.797(7)
_cell_formula_units_Z            2
_cell_length_a                   7.7137(5)
_cell_length_b                   9.9031(11)
_cell_length_c                   10.9047(11)
_cell_measurement_reflns_used    2150
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.7070
_cell_measurement_theta_min      3.4560
_cell_volume                     804.66(13)
_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      295(2)
_diffrn_detector_area_resol_mean 10.2496
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.963
_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  0.0681
_diffrn_reflns_av_unetI/netI     0.0837
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6563
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.924
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82033
_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    1.289
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.031(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3545
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.1416
_refine_ls_R_factor_gt           0.0808
_refine_ls_shift/su_max          0.063
_refine_ls_shift/su_mean         0.013
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.0586P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1835
_refine_ls_wR_factor_ref         0.2458
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1899
_reflns_number_total             3545
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao1c04086_si_003.cif
_cod_data_source_block           ic20101
_cod_database_code               4519104
_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'
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 0.3276(2) 0.61749(19) 0.86254(19) 0.0524(6) Uani 1 1 d . . . . .
O2 O 0.6706(3) 0.4029(2) 0.61013(19) 0.0558(6) Uani 1 1 d . . . . .
O3 O 0.3427(5) 0.8688(4) 1.0561(4) 0.0883(16) Uani 0.691(7) 1 d . . P A 1
O3' O 0.3446(13) 0.9392(8) 0.8864(9) 0.090(4) Uani 0.309(7) 1 d . . P A 2
O4 O 0.7159(3) 0.1107(2) 0.5278(3) 0.0801(8) Uani 1 1 d . . . . .
C1 C 0.2669(3) 0.4797(3) 0.8219(3) 0.0438(7) Uani 1 1 d . . . . .
C2 C 0.0871(3) 0.4149(3) 0.7939(3) 0.0537(8) Uani 1 1 d . . . . .
H2A H 0.000451 0.465340 0.800699 0.064 Uiso 1 1 calc R U . . .
C3 C 0.0371(4) 0.2752(3) 0.7558(3) 0.0614(9) Uani 1 1 d . . . . .
H3A H -0.083461 0.231297 0.736841 0.074 Uiso 1 1 calc R U . . .
C4 C 0.1644(4) 0.2015(3) 0.7459(3) 0.0654(9) Uani 1 1 d . . . . .
H4A H 0.130842 0.107090 0.721131 0.078 Uiso 1 1 calc R U . . .
C5 C 0.3444(4) 0.2679(3) 0.7731(3) 0.0546(8) Uani 1 1 d . . . . .
H5A H 0.430358 0.216978 0.765751 0.066 Uiso 1 1 calc R U . . .
C6 C 0.3989(3) 0.4077(3) 0.8108(2) 0.0423(7) Uani 1 1 d . . . . .
C7 C 0.5953(3) 0.4785(3) 0.8428(3) 0.0480(7) Uani 1 1 d . . . . .
H7A H 0.608865 0.523698 0.924949 0.058 Uiso 1 1 calc R U . . .
H7B H 0.662310 0.407115 0.845900 0.058 Uiso 1 1 calc R U . . .
C8 C 0.6795(3) 0.5854(3) 0.7565(3) 0.0435(7) Uani 1 1 d . . . . .
C9 C 0.7230(4) 0.7252(3) 0.7905(3) 0.0584(8) Uani 1 1 d . . . . .
H9A H 0.699571 0.754565 0.868323 0.070 Uiso 1 1 calc R U . . .
C10 C 0.8006(4) 0.8237(3) 0.7124(4) 0.0708(10) Uani 1 1 d . . . . .
H10A H 0.827928 0.918035 0.737106 0.085 Uiso 1 1 calc R U . . .
C11 C 0.8368(4) 0.7806(4) 0.5980(4) 0.0697(10) Uani 1 1 d . . . . .
H11A H 0.890106 0.846223 0.545262 0.084 Uiso 1 1 calc R U . . .
C12 C 0.7949(4) 0.6409(3) 0.5606(3) 0.0603(9) Uani 1 1 d . . . . .
H12A H 0.819649 0.612307 0.482956 0.072 Uiso 1 1 calc R U . . .
C13 C 0.7161(3) 0.5437(3) 0.6391(3) 0.0470(7) Uani 1 1 d . . . . .
C14 C 0.1993(4) 0.6938(3) 0.8900(3) 0.0602(9) Uani 1 1 d . . . . .
H14A H 0.125446 0.648919 0.951633 0.072 Uiso 1 1 calc R U . . .
H14B H 0.122095 0.698382 0.816357 0.072 Uiso 1 1 calc R U . . .
C15 C 0.2998(5) 0.8355(4) 0.9371(5) 0.0776(11) Uani 1 1 d . . . . .
H15 H 0.394189 0.878023 0.885807 0.093 Uiso 1 1 calc R U . A 1
C16 C 0.2150(6) 0.9325(4) 0.9905(5) 0.0964(14) Uani 1 1 d . . . . .
H16A H 0.089439 0.901124 1.004236 0.116 Uiso 1 1 calc R U . A 1
H16B H 0.254301 1.029548 0.972503 0.116 Uiso 1 1 calc R U . A 1
C17 C 0.6962(4) 0.3517(3) 0.4907(3) 0.0587(8) Uani 1 1 d . . . . .
H17A H 0.823133 0.368713 0.480341 0.070 Uiso 1 1 calc R U . . .
H17B H 0.640555 0.398340 0.427903 0.070 Uiso 1 1 calc R U . . .
C18 C 0.6127(4) 0.2004(3) 0.4794(3) 0.0631(9) Uani 1 1 d . . . . .
H18A H 0.484683 0.173856 0.491294 0.076 Uiso 1 1 calc R U . . .
C19 C 0.6738(5) 0.1078(4) 0.3982(4) 0.0819(11) Uani 1 1 d . . . . .
H19A H 0.585749 0.027557 0.359046 0.098 Uiso 1 1 calc R U . . .
H19B H 0.769571 0.147854 0.348501 0.098 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
C1 O1 C14 118.4(2) . . ?
C13 O2 C17 119.3(2) . . ?
C15 O3 C16 61.2(3) . . ?
C15 O3' C16 60.1(5) . . ?
C19 O4 C18 60.6(2) . . ?
O1 C1 C2 123.3(2) . . ?
O1 C1 C6 115.3(2) . . ?
C2 C1 C6 121.4(3) . . ?
C1 C2 C3 119.7(3) . . ?
C4 C3 C2 120.1(3) . . ?
C3 C4 C5 119.7(3) . . ?
C6 C5 C4 121.7(3) . . ?
C5 C6 C1 117.5(2) . . ?
C5 C6 C7 121.2(2) . . ?
C1 C6 C7 121.2(2) . . ?
C8 C7 C6 116.3(2) . . ?
C9 C8 C13 118.1(3) . . ?
C9 C8 C7 121.4(3) . . ?
C13 C8 C7 120.5(2) . . ?
C8 C9 C10 121.8(3) . . ?
C9 C10 C11 119.2(3) . . ?
C12 C11 C10 120.5(3) . . ?
C11 C12 C13 119.7(3) . . ?
O2 C13 C12 123.7(3) . . ?
O2 C13 C8 115.6(2) . . ?
C12 C13 C8 120.7(3) . . ?
O1 C14 C15 107.3(2) . . ?
O3' C15 C16 73.6(6) . . ?
O3 C15 C16 63.9(3) . . ?
O3' C15 C14 131.3(6) . . ?
O3 C15 C14 121.9(4) . . ?
C16 C15 C14 122.2(3) . . ?
C15 C16 O3 54.9(3) . . ?
C15 C16 O3' 46.3(3) . . ?
O2 C17 C18 107.5(3) . . ?
O4 C18 C19 59.8(2) . . ?
O4 C18 C17 117.4(3) . . ?
C19 C18 C17 121.4(3) . . ?
O4 C19 C18 59.6(2) . . ?
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 1.373(3) . ?
O1 C14 1.423(3) . ?
O2 C13 1.370(3) . ?
O2 C17 1.422(3) . ?
O3 C15 1.320(5) . ?
O3 C16 1.450(6) . ?
O3' C15 1.178(8) . ?
O3' C16 1.565(11) . ?
O4 C19 1.422(5) . ?
O4 C18 1.419(4) . ?
C1 C2 1.386(4) . ?
C1 C6 1.385(4) . ?
C2 C3 1.380(4) . ?
C3 C4 1.365(4) . ?
C4 C5 1.389(4) . ?
C5 C6 1.381(4) . ?
C6 C7 1.515(3) . ?
C7 C8 1.512(4) . ?
C8 C9 1.371(4) . ?
C8 C13 1.399(4) . ?
C9 C10 1.383(5) . ?
C10 C11 1.372(5) . ?
C11 C12 1.379(5) . ?
C12 C13 1.380(4) . ?
C14 C15 1.479(4) . ?
C15 C16 1.414(5) . ?
C17 C18 1.479(4) . ?
C18 C19 1.432(5) . ?
