Renewable Cyclobutane-1,3-dicarboxylic Acid (CBDA) Building Block Synthesized from Furfural via Photocyclization
Wang, Zhihan; Scheuring, Mark; Mabin, Micah; Shahni, Rahul; Wang, Zijun D.; Ugrinov, Angel; Butz, Jonathan; Chu, Qianli R.; ACS Sustainable Chemistry & Engineering  (2020) –; doi:10.1021/acssuschemeng.0c00708

data_4517757
_publ_section_title
;
 Renewable Cyclobutane-1,3-dicarboxylic Acid (CBDA) Building Block
 Synthesized from Furfural via Photocyclization
;
_journal_name_full               'ACS Sustainable Chemistry &amp; Engineering'
_journal_paper_doi               10.1021/acssuschemeng.0c00708
_journal_year                    2020
_chemical_formula_moiety         'C14 H12 O6'
_chemical_formula_sum            'C14 H12 O6'
_chemical_formula_weight         276.24
_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
_audit_creation_date             2020-01-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                73.144(4)
_cell_angle_beta                 68.207(4)
_cell_angle_gamma                86.546(4)
_cell_formula_units_Z            2
_cell_length_a                   8.2085(5)
_cell_length_b                   8.3297(5)
_cell_length_c                   10.3384(6)
_cell_measurement_reflns_used    796
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     627.27(7)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.99
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  Bruker
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_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       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6182
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.130
_diffrn_reflns_theta_max         25.130
_diffrn_reflns_theta_min         2.861
_exptl_absorpt_coefficient_mu    0.116
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0433
_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/[\s^2^(Fo^2^)+(0.0583P)^2^+0.3074P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1247
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1869
_reflns_number_total             2221
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sc0c00708_si_002.cif
_cod_data_source_block           cbda_5_0m
_cod_database_code               4517757
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.934
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5A), C6(H6), C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C8(H8), C9(H9), C10(H10), C13(H13)
;
_shelx_res_checksum              62200
_shelx_hkl_checksum              95921
_olex2_submission_special_instructions 'No special instructions were received'