# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mcg218
_database_code_depnum_ccdc_archive 'CCDC 2082537'
loop_
_audit_author_name
_audit_author_address
'Changan Li'
;University of Iowa
United States of America
;
_audit_update_record             
;
2021-05-08 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_audit_creation_date             2021-02-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
changan-li@uiowa.edu
michael-sinnwell@uiowa.edu
dale-swenson@uiowa.edu
len-macgillivray@uiowa.edu
_chemical_name_common            CAÂ.DMPÂ.2H2O
_chemical_name_systematic        
'(4-Oxo-4H-pyran-2,6-dicarboxylic acid)(2,6-dimethyl-4H-pyran-4-one)2H2O'
_chemical_formula_moiety         'C7 H4 O6, C7 H8 O2, 2(H2 O)'
_chemical_formula_sum            'C14 H16 O10'
_chemical_formula_weight         344.27
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2125(17)
_cell_length_b                   9.891(2)
_cell_length_c                   11.508(3)
_cell_angle_alpha                64.766(10)
_cell_angle_beta                 85.376(8)
_cell_angle_gamma                74.390(10)
_cell_volume                     813.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8412
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.3
_cell_measurement_theta_min      2.345
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0885 before and 0.0426 after correction.
The Ratio of minimum to maximum transmission is 0.9564.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism-like
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.125
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   1.0000
_exptl_transmission_factor_min   0.9564
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_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       -14
_diffrn_reflns_number            20353
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.382
_diffrn_reflns_theta_min         2.345
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture Duo'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2439
_reflns_number_total             3320
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0722P)²+0.1115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1333
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O9(H9A,H9B), O10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C14(H14), C9(H9)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O6 O 0.32994(14) 0.69677(12) 0.36386(10) 0.0510(3) Uani 1 1 d . . . . .
O8 O 0.05223(15) 0.12773(13) 0.09250(10) 0.0598(3) Uani 1 1 d . . . . .
O4 O 0.17160(18) 0.37056(15) 0.47403(12) 0.0681(4) Uani 1 1 d . . . . .
H4 H 0.147293 0.322835 0.437533 0.102 Uiso 1 1 calc GR . . . .
O1 O 0.49125(19) 1.00315(15) 0.33285(11) 0.0689(4) Uani 1 1 d . . . . .
H1 H 0.512091 1.075379 0.269538 0.103 Uiso 1 1 calc GR . . . .
O7 O 0.06608(18) 0.20199(15) 0.40982(12) 0.0704(4) Uani 1 1 d . . . . .
O5 O 0.3268(2) 0.60811(16) 0.74171(11) 0.0756(4) Uani 1 1 d . . . . .
O2 O 0.4497(2) 0.92070(17) 0.18874(12) 0.0830(5) Uani 1 1 d . . . . .
O3 O 0.2130(2) 0.53245(17) 0.27602(13) 0.0843(5) Uani 1 1 d . . . . .
O9 O 0.5485(2) 1.23680(18) 0.15675(13) 0.0832(5) Uani 1 1 d . . . . .
H9A H 0.594220 1.289624 0.179563 0.125 Uiso 1 1 d G . . . .
H9B H 0.582390 1.242926 0.083353 0.125 Uiso 1 1 d G . . . .
O10 O 0.6585(2) 1.2402(2) -0.06744(13) 0.0929(5) Uani 1 1 d . . . . .
H10A H 0.624030 1.190284 -0.100612 0.139 Uiso 1 1 d G . . . .
H10B H 0.687539 1.316492 -0.126584 0.139 Uiso 1 1 d G . . . .
C2 C 0.38633(19) 0.78599(17) 0.40610(14) 0.0473(4) Uani 1 1 d . . . . .
C6 C 0.2738(2) 0.57698(17) 0.45209(15) 0.0483(4) Uani 1 1 d . . . . .
C3 C 0.3874(2) 0.76258(18) 0.52919(15) 0.0509(4) Uani 1 1 d . . . . .
H3 H 0.426084 0.828133 0.552382 0.061 Uiso 1 1 calc R . . . .
C5 C 0.2719(2) 0.54313(19) 0.57737(16) 0.0540(4) Uani 1 1 d . . . . .
H5 H 0.233454 0.458699 0.633809 0.065 Uiso 1 1 calc R . . . .
C1 C 0.4468(2) 0.91057(19) 0.29688(15) 0.0550(4) Uani 1 1 d . . . . .
C10 C -0.0078(2) 0.03914(19) 0.20420(16) 0.0535(4) Uani 1 1 d . . . . .
C7 C 0.2153(2) 0.49013(19) 0.39066(16) 0.0538(4) Uani 1 1 d . . . . .
C8 C 0.0636(2) 0.18150(19) 0.30911(15) 0.0546(4) Uani 1 1 d . . . . .
C4 C 0.3287(2) 0.63596(19) 0.62721(15) 0.0539(4) Uani 1 1 d . . . . .
C14 C 0.1255(2) 0.2711(2) 0.18971(16) 0.0581(4) Uani 1 1 d . . . . .
H14 H 0.170857 0.350647 0.182849 0.070 Uiso 1 1 calc R . . . .
C9 C -0.0032(2) 0.06177(19) 0.31028(16) 0.0571(4) Uani 1 1 d . . . . .
H9 H -0.044068 -0.001478 0.386030 0.068 Uiso 1 1 calc R . . . .
C12 C 0.1189(2) 0.2416(2) 0.08686(16) 0.0585(4) Uani 1 1 d . . . . .
C11 C -0.0733(3) -0.0802(2) 0.19143(18) 0.0685(5) Uani 1 1 d . . . . .
H11A H -0.164910 -0.030545 0.128152 0.103 Uiso 1 1 calc GR . . . .
H11B H -0.113051 -0.141486 0.272657 0.103 Uiso 1 1 calc GR . . . .
H11C H 0.015644 -0.145781 0.165211 0.103 Uiso 1 1 calc GR . . . .
C13 C 0.1806(3) 0.3225(3) -0.04262(19) 0.0861(7) Uani 1 1 d . . . . .
H13A H 0.268985 0.250319 -0.062436 0.129 Uiso 1 1 calc GR . . . .
H13B H 0.223910 0.404157 -0.043947 0.129 Uiso 1 1 calc GR . . . .
H13C H 0.089009 0.365456 -0.105320 0.129 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O6 C2 1.3607(17) . ?
O6 C6 1.3563(19) . ?
O8 C10 1.354(2) . ?
O8 C12 1.3551(19) . ?
O4 C7 1.286(2) . ?
O1 C1 1.2923(19) . ?
O7 C8 1.2613(19) . ?
O5 C4 1.2254(19) . ?
O2 C1 1.2039(19) . ?
O3 C7 1.202(2) . ?
C2 C3 1.335(2) . ?
C2 C1 1.501(2) . ?
C6 C5 1.334(2) . ?
C6 C7 1.504(2) . ?
C3 C4 1.451(2) . ?
C5 C4 1.454(2) . ?
C10 C9 1.337(2) . ?
C10 C11 1.486(2) . ?
C8 C14 1.422(2) . ?
C8 C9 1.428(2) . ?
C14 C12 1.342(2) . ?
C12 C13 1.482(2) . ?

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 O6 C2 117.99(12) . . ?
C10 O8 C12 120.04(12) . . ?
O6 C2 C1 111.03(12) . . ?
C3 C2 O6 123.39(14) . . ?
C3 C2 C1 125.58(14) . . ?
O6 C6 C7 111.66(13) . . ?
C5 C6 O6 123.06(14) . . ?
C5 C6 C7 125.28(14) . . ?
C2 C3 C4 120.71(14) . . ?
C6 C5 C4 121.12(15) . . ?
O1 C1 C2 112.39(13) . . ?
O2 C1 O1 125.47(16) . . ?
O2 C1 C2 122.13(15) . . ?
O8 C10 C11 111.97(14) . . ?
C9 C10 O8 121.19(14) . . ?
C9 C10 C11 126.84(15) . . ?
O4 C7 C6 112.31(14) . . ?
O3 C7 O4 126.30(15) . . ?
O3 C7 C6 121.39(15) . . ?
O7 C8 C14 124.11(15) . . ?
O7 C8 C9 120.24(15) . . ?
C14 C8 C9 115.64(14) . . ?
O5 C4 C3 123.88(14) . . ?
O5 C4 C5 122.39(15) . . ?
C3 C4 C5 113.73(13) . . ?
C12 C14 C8 120.52(15) . . ?
C10 C9 C8 121.04(15) . . ?
O8 C12 C13 111.65(15) . . ?
C14 C12 O8 121.57(15) . . ?
C14 C12 C13 126.78(17) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H4 O7 0.82 1.66 2.4511(16) 160.7 . yes
O1 H1 O9 0.82 1.66 2.4709(18) 170.6 . yes
O9 H9A O5 0.85 1.87 2.7083(17) 169.2 2_676 yes
O9 H9B O10 0.85 1.81 2.653(2) 175.7 . yes
O10 H10A O2 0.85 2.00 2.8505(19) 176.4 2_675 yes
O10 H10B O3 0.85 2.02 2.863(2) 169.2 2_675 yes

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mcg2151_5
_database_code_depnum_ccdc_archive 'CCDC 2082538'
loop_
_audit_author_name
_audit_author_address
'Changan Li'
;University of Iowa
United States of America
;
_audit_update_record             
;
2021-05-08 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_audit_creation_date             2021-04-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
changan-li@uiowa.edu
michael-sinnwell@uiowa.edu
dale-swenson@uiowa.edu
len-macgillivray@uiowa.edu
_chemical_name_common            'tetraacid cage CG1'
_chemical_name_systematic        
'6,6,12,12-tetrahydroxy-3,9-dioxapentacyclo[6.4.0.0^2,7.0^4,11.0^5,10]dodecane-2,4,8,10-tetracarboxylic acid hydrate'
_chemical_formula_moiety         'C14.61 H13.22 O14, 4(H2 O), 2(H1.7 O0.7)'
_chemical_formula_sum            'C14.61 H24.61 O19.39'
_chemical_formula_weight         510.51
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7763(19)
_cell_length_b                   8.1868(17)
_cell_length_c                   8.683(2)
_cell_angle_alpha                82.568(7)
_cell_angle_beta                 82.756(8)
_cell_angle_gamma                65.804(6)
_cell_volume                     498.4(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9198
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.92
_cell_measurement_theta_min      2.3725
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1218 before and 0.0527 after correction.
The Ratio of minimum to maximum transmission is 0.8822.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plates
_exptl_crystal_F_000             267
_exptl_crystal_size_max          0.105
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   1.0000
_exptl_transmission_factor_min   0.8822
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0767
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1743
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.020
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         2.373
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Venture Duo'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1220
_reflns_number_total             1743
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         1743
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0605
_refine_ls_restrained_S_all      1.068
_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)+1.2197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1424
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.786(3)
 0.214(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
3. Shared sites
{O2, O2'}
4. Restrained distances
 O1A-H1AA
 0.84 with sigma of 0.02
5. Uiso/Uaniso restraints and constraints
Uanis(O2) = Uanis(O2')
6. Others
 Sof(O2')=Sof(C1')=Sof(H1'A)=Sof(H1'B)=Sof(H1'C)=1-FVAR(1)
 Sof(O2)=Sof(H2)=Sof(O1A)=Sof(H1AA)=FVAR(1)
7.a Free rotating group:
 O3A(H3AA,H3AB), O2A(H2AA,H2AB)
7.b Ternary CH refined with riding coordinates:
 C3(H3), C5(H5A)
7.c Me refined with riding coordinates:
 C1'(H1'A,H1'B,H1'C)
7.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O7(H7), O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.6947(4) 0.4024(4) 0.8419(3) 0.0236(7) Uani 1 1 d . . . . .
O5 O 0.1510(4) 0.7987(4) 0.8709(4) 0.0280(7) Uani 1 1 d . . . . .
O4 O 0.4021(4) 0.6908(4) 0.6817(3) 0.0292(7) Uani 1 1 d . . . . .
H4 H 0.359202 0.638030 0.629989 0.044 Uiso 1 1 calc GR . . . .
O7 O 0.8604(4) 0.7137(4) 0.9388(4) 0.0327(8) Uani 1 1 d . . . . .
H7 H 0.958865 0.729021 0.903501 0.049 Uiso 1 1 calc GR . . . .
O6 O 0.9344(5) 0.5430(5) 0.7391(4) 0.0385(9) Uani 1 1 d . . . . .
O3A O 0.1071(5) 1.1298(4) 0.7583(4) 0.0405(9) Uani 1 1 d . . . . .
H3AA H -0.008220 1.210635 0.767527 0.061 Uiso 1 1 d G . . . .
H3AB H 0.175486 1.179861 0.787956 0.061 Uiso 1 1 d G . . . .
O3 O 0.4610(5) 0.1229(4) 0.8014(4) 0.0406(9) Uani 1 1 d . . . . .
O2A O 0.2626(6) 0.5105(7) 0.5315(5) 0.0685(13) Uani 1 1 d . . . . .
H2AA H 0.279301 0.490800 0.433492 0.103 Uiso 1 1 d G . . . .
H2AB H 0.142560 0.550078 0.561392 0.103 Uiso 1 1 d G . . . .
C6 C 0.6779(6) 0.5473(5) 0.9259(5) 0.0218(9) Uani 1 1 d . . . . .
C3 C 0.3449(6) 0.4886(6) 0.8941(5) 0.0231(10) Uani 1 1 d . . . . .
H3 H 0.256714 0.458624 0.840020 0.028 Uiso 1 1 calc R . . . .
C4 C 0.3404(6) 0.6744(6) 0.8393(5) 0.0230(9) Uani 1 1 d . . . . .
C5 C 0.4776(6) 0.7070(6) 0.9303(5) 0.0241(10) Uani 1 1 d . . . . .
H5A H 0.482550 0.827478 0.901838 0.029 Uiso 1 1 calc R . . . .
C1 C 0.5775(6) 0.1860(6) 0.7927(5) 0.0265(10) Uani 1 1 d . . . . .
C2 C 0.5504(6) 0.3375(6) 0.8895(5) 0.0233(9) Uani 1 1 d . . . . .
C7 C 0.8382(6) 0.6007(6) 0.8574(5) 0.0249(9) Uani 1 1 d . . . . .
H5 H 0.149(9) 0.906(9) 0.838(8) 0.09(2) Uiso 1 1 d . . . . .
O2 O 0.7375(5) 0.1299(5) 0.7055(4) 0.0419(9) Uani 0.695(14) 1 d . . P A 1
H2 H 0.743727 0.046361 0.655275 0.063 Uiso 0.695(14) 1 calc GR . P A 1
O1A O 0.7073(13) -0.1016(9) 0.5395(9) 0.083(3) Uani 0.695(14) 1 d D . P A 1
H1AA H 0.781(16) -0.119(19) 0.456(10) 0.15(6) Uiso 0.695(14) 1 d D . P A 1
O2' O 0.7375(5) 0.1299(5) 0.7055(4) 0.0419(9) Uani 0.305(14) 1 d . . P A 2
C1' C 0.777(3) -0.005(3) 0.597(2) 0.051(6) Uani 0.305(14) 1 d . . P A 2
H1'A H 0.902323 -0.030648 0.541642 0.076 Uiso 0.305(14) 1 calc R . P A 2
H1'B H 0.774921 -0.115432 0.654091 0.076 Uiso 0.305(14) 1 calc R . P A 2
H1'C H 0.681049 0.040359 0.521120 0.076 Uiso 0.305(14) 1 calc R . P A 2
H1A H 0.61(4) -0.19(3) 0.55(3) 0.54(17) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 1.425(5) . ?
O1 C2 1.424(5) . ?
O5 C4 1.422(5) . ?
O4 C4 1.400(5) . ?
O7 C7 1.310(5) . ?
O6 C7 1.216(5) . ?
O3 C1 1.204(5) . ?
C6 C3 1.554(6) 2_667 ?
C6 C5 1.570(6) . ?
C6 C7 1.514(6) . ?
C3 C4 1.522(6) . ?
C3 C2 1.569(6) . ?
C4 C5 1.529(6) . ?
C5 C2 1.569(6) 2_667 ?
C1 C2 1.516(6) . ?
C1 O2 1.310(5) . ?
C1 O2' 1.310(5) . ?
O2' C1' 1.458(15) . ?

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
C2 O1 C6 113.1(3) . . ?
O1 C6 C3 114.4(3) . 2_667 ?
O1 C6 C5 114.9(3) . . ?
O1 C6 C7 105.6(3) . . ?
C3 C6 C5 90.0(3) 2_667 . ?
C7 C6 C3 117.6(4) . 2_667 ?
C7 C6 C5 114.3(3) . . ?
C6 C3 C2 90.4(3) 2_667 . ?
C4 C3 C6 114.0(3) . 2_667 ?
C4 C3 C2 113.0(3) . . ?
O5 C4 C3 106.5(3) . . ?
O5 C4 C5 111.5(4) . . ?
O4 C4 O5 111.6(3) . . ?
O4 C4 C3 113.1(3) . . ?
O4 C4 C5 106.1(3) . . ?
C3 C4 C5 108.2(3) . . ?
C4 C5 C6 111.9(3) . . ?
C4 C5 C2 112.8(3) . 2_667 ?
C2 C5 C6 89.8(3) 2_667 . ?
O3 C1 C2 121.1(4) . . ?
O3 C1 O2 124.6(4) . . ?
O3 C1 O2' 124.6(4) . . ?
O2 C1 C2 114.2(4) . . ?
O2' C1 C2 114.2(4) . . ?
O1 C2 C3 113.9(3) . . ?
O1 C2 C5 114.9(3) . 2_667 ?
O1 C2 C1 109.5(3) . . ?
C3 C2 C5 89.5(3) . 2_667 ?
C1 C2 C3 113.7(3) . . ?
C1 C2 C5 114.2(3) . 2_667 ?
O7 C7 C6 112.8(3) . . ?
O6 C7 O7 124.7(4) . . ?
O6 C7 C6 122.5(4) . . ?
C1 O2' C1' 120.6(8) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.786(3)
2 0.214(3)

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH/benzene'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mcg1748a
_database_code_depnum_ccdc_archive 'CCDC 2082540'
loop_
_audit_author_name
_audit_author_address
'Changan Li'
;University of Iowa
United States of America
;
_audit_update_record             
;
2021-05-08 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_audit_creation_date             2020-10-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
changan-li@uiowa.edu
michael-sinnwell@uiowa.edu
dale-swenson@uiowa.edu
len-macgillivray@uiowa.edu
_chemical_name_common            'tetramethyl cage'
_chemical_name_systematic        
'2,4,8,10-tetramethyl-3,9-dioxapentacyclo [6.4.0.0^2,7.0^4,11.0^5,10]dodecane-6,12-dione '
_chemical_formula_moiety         'C14 H16 O4'
_chemical_formula_sum            'C14 H16 O4'
_chemical_formula_weight         248.27
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c a'
_space_group_name_Hall           '-C 2bc 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'x+1/2, -y, z-1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   12.4105(12)
_cell_length_b                   7.2547(7)
_cell_length_c                   13.7901(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1241.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1652
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1.00
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9874
_exptl_absorpt_correction_T_min  0.7913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3393
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.348
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         4.396
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker Nonius APEX II Kappa'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                507
_reflns_number_total             598
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     49
_refine_ls_number_reflns         598
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.052
_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)+(0.0574P)²+0.6082P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1167
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5)
2.b Idealised Me refined as rotating group:
 C6(H6a,H6b,H6c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.34976(11) 0.500000 0.500000 0.0505(5) Uani 1 2 d S T P . .
O7 O 0.500000 0.8439(2) 0.35922(11) 0.0738(7) Uani 1 2 d S T P . .
C2 C 0.41174(12) 0.6016(2) 0.56889(10) 0.0437(5) Uani 1 1 d . . . . .
C3 C 0.500000 0.7251(3) 0.52081(14) 0.0461(6) Uani 1 2 d S T P . .
H3 H 0.500000 0.852257 0.544816 0.055 Uiso 1 2 calc R U P . .
C4 C 0.500000 0.7122(3) 0.41303(15) 0.0482(6) Uani 1 2 d S T P . .
C5 C 0.500000 0.5175(3) 0.37968(14) 0.0433(6) Uani 1 2 d S T P . .
H5 H 0.500000 0.504655 0.308937 0.052 Uiso 1 2 calc R U P . .
C6 C 0.33323(15) 0.6993(3) 0.63405(12) 0.0639(6) Uani 1 1 d . . . . .
H6A H 0.290476 0.783120 0.596352 0.096 Uiso 1 1 calc R U . . .
H6B H 0.372014 0.766686 0.682747 0.096 Uiso 1 1 calc R U . . .
H6C H 0.287066 0.610493 0.664664 0.096 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C2 1.4274(16) . ?
O1 C2 1.4275(16) 4_566 ?
O7 C4 1.210(3) . ?
C2 C3 1.563(2) . ?
C2 C5 1.565(2) 9_666 ?
C2 C6 1.503(2) . ?
C3 H3 0.9800 . ?
C3 C4 1.489(3) . ?
C4 C5 1.485(3) . ?
C5 H5 0.9800 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?

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
C2 O1 C2 114.78(15) . 4_566 ?
O1 C2 C3 113.04(12) . . ?
O1 C2 C5 113.18(12) . 9_666 ?
O1 C2 C6 106.98(13) . . ?
C3 C2 C5 91.05(11) . 9_666 ?
C6 C2 C3 115.95(14) . . ?
C6 C2 C5 116.30(13) . 9_666 ?
C2 C3 C2 88.99(15) 12_655 . ?
C2 C3 H3 113.3 12_655 . ?
C2 C3 H3 113.3 . . ?
C4 C3 C2 112.79(12) . . ?
C4 C3 C2 112.80(12) . 12_655 ?
C4 C3 H3 113.3 . . ?
O7 C4 C3 124.2(2) . . ?
O7 C4 C5 124.14(19) . . ?
C5 C4 C3 111.64(18) . . ?
C2 C5 C2 88.83(14) 4_566 9_666 ?
C2 C5 H5 113.5 4_566 . ?
C2 C5 H5 113.5 9_666 . ?
C4 C5 C2 112.63(12) . 4_566 ?
C4 C5 C2 112.63(12) . 9_666 ?
C4 C5 H5 113.5 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

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
O1 C2 C3 C2 -113.77(11) . . . 12_655 ?
O1 C2 C3 C4 0.61(18) . . . . ?
O7 C4 C5 C2 130.69(10) . . . 9_666 ?
O7 C4 C5 C2 -130.69(10) . . . 4_566 ?
C2 O1 C2 C3 50.80(9) 4_566 . . . ?
C2 O1 C2 C5 -50.96(9) 4_566 . . 9_666 ?
C2 O1 C2 C6 179.63(14) 4_566 . . . ?
C2 C3 C4 O7 130.51(11) . . . . ?
C2 C3 C4 O7 -130.52(11) 12_655 . . . ?
C2 C3 C4 C5 -49.49(11) . . . . ?
C2 C3 C4 C5 49.48(11) 12_655 . . . ?
C3 C4 C5 C2 49.31(10) . . . 4_566 ?
C3 C4 C5 C2 -49.31(10) . . . 9_666 ?
C5 C2 C3 C2 2.05(14) 9_666 . . 12_655 ?
C5 C2 C3 C4 116.44(14) 9_666 . . . ?
C6 C2 C3 C2 122.18(12) . . . 12_655 ?
C6 C2 C3 C4 -123.43(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mcg2154
_database_code_depnum_ccdc_archive 'CCDC 2082539'
loop_
_audit_author_name
_audit_author_address
'Changan Li'
;University of Iowa
United States of America
;
_audit_update_record             
;
2021-05-08 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_audit_creation_date             2021-05-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
changan-li@uiowa.edu
michael-sinnwell@uiowa.edu
dale-swenson@uiowa.edu
len-macgillivray@uiowa.edu
_chemical_name_common            CAÂ.THF
_chemical_name_systematic        '(4-Oxo-4H-pyran-2,6-dicarboxylic acid)solvate'
_chemical_formula_moiety         'C7 H4 O6, C4 H8 O'
_chemical_formula_sum            'C11 H12 O7'
_chemical_formula_weight         256.21
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.6261(10)
_cell_length_b                   11.4586(11)
_cell_length_c                   11.0733(11)
_cell_angle_alpha                90
_cell_angle_beta                 111.621(5)
_cell_angle_gamma                90
_cell_volume                     1135.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    42194
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.27
_cell_measurement_theta_min      2.2755
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0634 before and 0.0426 after correction.
The Ratio of minimum to maximum transmission is 0.9649.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'irregular prism-like'
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.055
_exptl_transmission_factor_max   1.0000
_exptl_transmission_factor_min   0.9649
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            25641
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.389
_diffrn_reflns_theta_min         2.276
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture Duo'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2058
_reflns_number_total             2319
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0319
_refine_ls_restrained_S_all      1.099
_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)+(0.0354P)²+0.4626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0847
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5A)
2.c Idealised tetrahedral OH refined as rotating group:
 O5(H5), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O6 O 0.31531(9) 0.57296(7) 0.42525(8) 0.0210(2) Uani 1 1 d . . . . .
O3 O 0.37687(10) 0.92264(7) 0.40417(9) 0.0259(2) Uani 1 1 d . . . . .
O4 O 0.12588(11) 0.65645(8) 0.62781(9) 0.0290(2) Uani 1 1 d . . . . .
O5 O 0.18578(11) 0.48175(8) 0.56839(9) 0.0279(2) Uani 1 1 d . . . . .
H5 H 0.144017 0.455498 0.617285 0.042 Uiso 1 1 calc GR . . . .
O2 O 0.49938(11) 0.56272(8) 0.20592(9) 0.0293(2) Uani 1 1 d . . . . .
H2 H 0.534242 0.508251 0.174856 0.044 Uiso 1 1 calc GR . . . .
O1 O 0.42962(11) 0.41804(8) 0.30857(9) 0.0310(2) Uani 1 1 d . . . . .
O7 O 0.06421(11) 0.38322(8) 0.71463(9) 0.0283(2) Uani 1 1 d . . . . .
C2 C 0.39111(13) 0.61608(11) 0.35317(11) 0.0199(3) Uani 1 1 d . . . . .
C4 C 0.35852(13) 0.81597(10) 0.40901(11) 0.0208(3) Uani 1 1 d . . . . .
C3 C 0.41551(13) 0.73026(11) 0.34266(11) 0.0211(3) Uani 1 1 d . . . . .
H3 H 0.470421 0.755076 0.291458 0.025 Uiso 1 1 calc R . . . .
C5 C 0.27708(13) 0.76625(11) 0.48311(11) 0.0212(3) Uani 1 1 d . . . . .
H5A H 0.234615 0.816291 0.528676 0.025 Uiso 1 1 calc R . . . .
C1 C 0.44216(13) 0.51964(11) 0.28721(11) 0.0216(3) Uani 1 1 d . . . . .
C7 C 0.18188(13) 0.59598(11) 0.56897(12) 0.0215(3) Uani 1 1 d . . . . .
C6 C 0.26067(13) 0.65073(11) 0.48839(11) 0.0198(3) Uani 1 1 d . . . . .
C11 C 0.13770(18) 0.27388(13) 0.76513(15) 0.0363(3) Uani 1 1 d . . . . .
H11A H 0.206166 0.251383 0.720809 0.044 Uiso 1 1 calc R . . . .
H11B H 0.063445 0.210841 0.753074 0.044 Uiso 1 1 calc R . . . .
C8 C 0.04080(17) 0.44613(14) 0.81896(14) 0.0348(3) Uani 1 1 d . . . . .
H8A H -0.067198 0.450714 0.803147 0.042 Uiso 1 1 calc R . . . .
H8B H 0.080693 0.526465 0.825103 0.042 Uiso 1 1 calc R . . . .
C9 C 0.12247(19) 0.37961(14) 0.94317(14) 0.0402(4) Uani 1 1 d . . . . .
H9A H 0.051273 0.336504 0.972257 0.048 Uiso 1 1 calc R . . . .
H9B H 0.181988 0.433197 1.013271 0.048 Uiso 1 1 calc R . . . .
C10 C 0.22325(18) 0.29595(14) 0.90708(16) 0.0421(4) Uani 1 1 d . . . . .
H10A H 0.321604 0.331873 0.921460 0.051 Uiso 1 1 calc R . . . .
H10B H 0.238570 0.222774 0.957877 0.051 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O6 C2 1.3575(14) . ?
O6 C6 1.3531(14) . ?
O3 C4 1.2389(15) . ?
O4 C7 1.2057(15) . ?
O5 C7 1.3096(15) . ?
O2 C1 1.3126(15) . ?
O1 C1 1.2029(16) . ?
O7 C11 1.4462(17) . ?
O7 C8 1.4481(16) . ?
C2 C3 1.3419(17) . ?
C2 C1 1.5035(17) . ?
C4 C3 1.4499(17) . ?
C4 C5 1.4445(17) . ?
C5 C6 1.3369(18) . ?
C7 C6 1.5046(16) . ?
C11 C10 1.503(2) . ?
C8 C9 1.515(2) . ?
C9 C10 1.518(2) . ?

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 O6 C2 117.36(9) . . ?
C11 O7 C8 108.69(10) . . ?
O6 C2 C1 111.15(10) . . ?
C3 C2 O6 123.72(11) . . ?
C3 C2 C1 125.13(11) . . ?
O3 C4 C3 124.04(11) . . ?
O3 C4 C5 121.97(11) . . ?
C5 C4 C3 113.99(11) . . ?
C2 C3 C4 120.36(11) . . ?
C6 C5 C4 120.86(11) . . ?
O2 C1 C2 110.59(10) . . ?
O1 C1 O2 126.63(11) . . ?
O1 C1 C2 122.78(11) . . ?
O4 C7 O5 126.61(11) . . ?
O4 C7 C6 120.28(11) . . ?
O5 C7 C6 113.09(10) . . ?
O6 C6 C7 114.12(10) . . ?
C5 C6 O6 123.70(11) . . ?
C5 C6 C7 122.16(11) . . ?
O7 C11 C10 105.07(12) . . ?
O7 C8 C9 107.02(12) . . ?
C8 C9 C10 104.30(12) . . ?
C11 C10 C9 102.97(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
