Syntheses and crystal structures of the anhydride 4-oxatetracyclo[5.3.2.0^2,6^.0^8,10^]dodec-11-ene-3,5-dione and the related imide 4-(4-bromophenyl)-4-azatetracyclo[5.3.2.0^2,6^.0^8,10^]dodec-11-ene-3,5-dione
Hulsman, Andrew; Lorenzana, Isabel; Schultz, Theodore; Squires, Breezy; Stenfors, Brock A.; Tolonen, Mason; Staples, Richard J.; Biros, Shannon M.; Winchester, William R.; Acta Crystallographica Section E 76 (2020) 1311–1315; doi:10.1107/S2056989020009512

data_2243493
_publ_section_title
;
 Syntheses and crystal structures of the anhydride
 4-oxatetracyclo[5.3.2.0^2,6^.0^8,10^]dodec-11-ene-3,5-dione and the
 related imide
 4-(4-bromophenyl)-4-azatetracyclo[5.3.2.0^2,6^.0^8,10^]dodec-11-ene-3,5-dione
;
_journal_coeditor_code           HB7931
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1311
_journal_page_last               1315
_journal_paper_doi               10.1107/S2056989020009512
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C11 H10 O3'
_chemical_formula_moiety         'C11 H10 O3'
_chemical_formula_sum            'C11 H10 O3'
_chemical_formula_weight         190.19
_chemical_name_systematic
;
4-Oxatetracyclo[5.3.2.0^2,6^.0^8,10^]dodec-11-ene-3,5-dione
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 92.6226(15)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.3538(3)
_cell_length_b                   7.4062(2)
_cell_length_c                   20.5398(5)
_cell_measurement_reflns_used    8934
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.400
_cell_measurement_theta_min      3.897
_cell_volume                     1725.35(8)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009; Bourhis <i>et al.</i>,
2015)
;
_computing_publication_material
;
CrystalMaker (Palmer, 2007)
;
_computing_structure_refinement
;
ShelXL (Sheldrick, 2015)
;
_computing_structure_solution
;
ShelXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13466
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.394
_diffrn_reflns_theta_min         4.309
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.884
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       chunk
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.526
_exptl_crystal_size_mid          0.322
_exptl_crystal_size_min          0.223
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.398
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0673P)^2^+0.5724P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1163
_reflns_number_gt                3070
_reflns_number_total             3353
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7931sup1.cif
_cod_data_source_block           I
_cod_database_code               2243493
_cod_database_fobs_code          2243493
_shelx_estimated_absorpt_t_min   0.653
_shelx_estimated_absorpt_t_max   0.827