Cubane-forming cyclic dienes that exhibit orthogonal reactivities in the solid state.
Li, Changan; Sinnwell, Michael A.; Swenson, Dale C.; MacGillivray, Leonard R.; Chemical communications (Cambridge, England) 57 (2021) 6725–6727; doi:10.1039/d1cc02725e

data_7128449
_publ_section_title
;
 Cubane-forming cyclic dienes that exhibit orthogonal reactivities in the
 solid state.
;
_journal_issue                   55
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6725
_journal_page_last               6727
_journal_paper_doi               10.1039/d1cc02725e
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C7 H4 O6, C7 H8 O2, 2(H2 O)'
_chemical_formula_sum            'C14 H16 O10'
_chemical_formula_weight         344.27
_chemical_name_common            CA\^A.DMP\^A.2H2O
_chemical_name_systematic
'(4-Oxo-4H-pyran-2,6-dicarboxylic acid)(2,6-dimethyl-4H-pyran-4-one)2H2O'
_chemical_properties_physical    Light-sensitive
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-08 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                64.766(10)
_cell_angle_beta                 85.376(8)
_cell_angle_gamma                74.390(10)
_cell_formula_units_Z            2
_cell_length_a                   8.2125(17)
_cell_length_b                   9.891(2)
_cell_length_c                   11.508(3)
_cell_measurement_reflns_used    8412
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.3
_cell_measurement_theta_min      2.345
_cell_volume                     813.8(3)
_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)'
_diffrn_ambient_temperature      298.15
_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_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
_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 \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.405
_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
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.035
_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_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0415
_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/[\s^2^(Fo^2^)+(0.0722P)^2^+0.1115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1333
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2439
_reflns_number_total             3320
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02725e2.cif
_cod_data_source_block           mcg218
_cod_depositor_comments
'Adding full bibliography for 7128449--7128452.cif.'
_cod_original_cell_volume        813.7(3)
_cod_database_code               7128449
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.985
_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)
;
_shelx_res_checksum              2267
_olex2_submission_special_instructions 'No special instructions were received'