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#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/48/7234812.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_7234812
loop_
_publ_author_name
'Zhou, Hui'
'Zhang, Hui'
'Mu, Sen'
'Zhang, Wen-Zhen'
'Ren, Wei-Min'
'Lu, Xiaobing'
_publ_section_title
;
 Highly Regio- and Stereoselective Synthesis of Cyclic Carbonates from
 Biomass-derived Polyols via Organocatalytic Cascade Reaction
;
_journal_name_full               'Green Chemistry'
_journal_paper_doi               10.1039/C9GC03013A
_journal_year                    2019
_chemical_formula_sum            'C6 H6 O6'
_chemical_formula_weight         174.11
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-07-14 deposited with the CCDC.    2019-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.2550(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6926(10)
_cell_length_b                   5.2936(5)
_cell_length_c                   12.0745(11)
_cell_measurement_reflns_used    3361
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.34
_cell_volume                     658.31(10)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.957
_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  0.0181
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3725
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_min         3.342
_exptl_absorpt_coefficient_mu    0.163
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.298
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.298
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0380
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1399
_refine_ls_wR_factor_ref         0.1448
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1054
_reflns_number_total             1147
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9gc03013a2.cif
_cod_data_source_block           work1
_cod_database_code               7234812
_shelx_shelxl_version_number     2016/6
_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
O1 O 0.12454(11) 0.7536(3) 0.32962(11) 0.0354(4) Uani 1 1 d . .
O2 O 0.07958(11) 1.0223(2) 0.17145(10) 0.0230(4) Uani 1 1 d . .
O3 O 0.13717(11) 0.6300(2) 0.15842(12) 0.0285(4) Uani 1 1 d . .
O4 O 0.32788(10) 0.8073(2) 0.62467(11) 0.0326(4) Uani 1 1 d . .
O5 O 0.17779(11) 0.50700(19) 0.58240(11) 0.0222(4) Uani 1 1 d . .
O6 O 0.14592(11) 0.8900(2) 0.63559(11) 0.0269(4) Uani 1 1 d . .
C1 C 0.11433(14) 0.7975(3) 0.22862(15) 0.0233(5) Uani 1 1 d . .
C2 C 0.07171(17) 1.0059(3) 0.04822(15) 0.0207(4) Uani 1 1 d . .
H2 H 0.114794 1.154337 0.032276 0.025 Uiso 1 1 calc R U
C3 C 0.14528(16) 0.7649(3) 0.05776(16) 0.0279(5) Uani 1 1 d . .
H3A H 0.103724 0.668142 -0.021855 0.033 Uiso 1 1 calc R U
H3B H 0.236624 0.800594 0.079482 0.033 Uiso 1 1 calc R U
C4 C 0.22629(15) 0.7418(3) 0.61506(14) 0.0226(4) Uani 1 1 d . .
C5 C 0.04864(16) 0.4993(3) 0.57027(15) 0.0189(4) Uani 1 1 d . .
H5 H 0.037095 0.345317 0.611930 0.023 Uiso 1 1 calc R U
C6 C 0.04523(16) 0.7369(3) 0.63910(15) 0.0248(5) Uani 1 1 d . .
H6A H -0.040398 0.821199 0.595275 0.030 Uiso 1 1 calc R U
H6B H 0.065048 0.698909 0.726664 0.030 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
C1 O2 C2 109.40(11) . .
C1 O3 C3 108.44(13) . .
C4 O5 C5 109.31(11) . .
C4 O6 C6 109.28(12) . .
O1 C1 O3 124.48(16) . .
O1 C1 O2 124.08(16) . .
O3 C1 O2 111.43(13) . .
O2 C2 C3 102.42(12) . .
O2 C2 C2 107.39(15) . 3_575
C3 C2 C2 113.83(16) . 3_575
O2 C2 H2 110.9 . .
C3 C2 H2 110.9 . .
C2 C2 H2 110.9 3_575 .
O3 C3 C2 102.63(11) . .
O3 C3 H3A 111.2 . .
C2 C3 H3A 111.2 . .
O3 C3 H3B 111.2 . .
C2 C3 H3B 111.2 . .
H3A C3 H3B 109.2 . .
O4 C4 O6 124.68(16) . .
O4 C4 O5 124.12(15) . .
O6 C4 O5 111.20(13) . .
O5 C5 C6 102.58(12) . .
O5 C5 C5 107.71(15) . 3_566
C6 C5 C5 113.84(16) . 3_566
O5 C5 H5 110.8 . .
C6 C5 H5 110.8 . .
C5 C5 H5 110.8 3_566 .
O6 C6 C5 102.45(11) . .
O6 C6 H6A 111.3 . .
C5 C6 H6A 111.3 . .
O6 C6 H6B 111.3 . .
C5 C6 H6B 111.3 . .
H6A C6 H6B 109.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.1907(18) .
O2 C1 1.339(2) .
O2 C2 1.4494(18) .
O3 C1 1.338(2) .
O3 C3 1.4509(19) .
O4 C4 1.1892(19) .
O5 C4 1.345(2) .
O5 C5 1.4470(19) .
O6 C4 1.3346(19) .
O6 C6 1.4465(19) .
C2 C3 1.512(2) .
C2 C2 1.524(3) 3_575
C2 H2 1.0000 .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C5 C6 1.518(2) .
C5 C5 1.532(3) 3_566
C5 H5 1.0000 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
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_4
C3 O3 C1 O1 -166.49(15) . .
C3 O3 C1 O2 12.93(18) . .
C2 O2 C1 O1 -177.66(14) . .
C2 O2 C1 O3 2.92(18) . .
C1 O2 C2 C3 -16.43(16) . .
C1 O2 C2 C2 103.74(16) . 3_575
C1 O3 C3 C2 -22.24(17) . .
O2 C2 C3 O3 22.58(16) . .
C2 C2 C3 O3 -93.01(18) 3_575 .
C6 O6 C4 O4 -168.99(15) . .
C6 O6 C4 O5 10.76(17) . .
C5 O5 C4 O4 -175.53(14) . .
C5 O5 C4 O6 4.71(17) . .
C4 O5 C5 C6 -16.98(16) . .
C4 O5 C5 C5 103.41(16) . 3_566
C4 O6 C6 C5 -20.52(16) . .
O5 C5 C6 O6 21.85(15) . .
C5 C5 C6 O6 -94.21(18) 3_566 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339080
