Syntheses, crystal structures and Hirshfeld surface analyses of (3a<i>R</i>,4<i>S</i>,7<i>R</i>,7a<i>S</i>)-2-(perfluoropyridin-4-yl)-3a,4,7,7a-tetrahydro-4,7-methanoisoindole-1,3-dione and (3a<i>R</i>,4<i>S</i>,7<i>R</i>,7a<i>S</i>)-2-[(perfluoropyridin-4-yl)oxy]-3a,4,7,7a-tetrahydro-4,7-methanoisoindole-1,3-dione
Peloquin, Andrew J.; Balaich, Gary J.; Iacono, Scott T.; Acta Crystallographica Section E 75 (2019) 1153–1157; doi:10.1107/S2056989019009769

data_2243013
_publ_section_title
;
 Syntheses, crystal structures and Hirshfeld surface analyses of
 (3a<i>R</i>,4<i>S</i>,7<i>R</i>,7a<i>S</i>)-2-(perfluoropyridin-4-yl)-3a,4,7,7a-tetrahydro-4,7-methanoisoindole-1,3-dione
 and
 (3a<i>R</i>,4<i>S</i>,7<i>R</i>,7a<i>S</i>)-2-[(perfluoropyridin-4-yl)oxy]-3a,4,7,7a-tetrahydro-4,7-methanoisoindole-1,3-dione
;
_journal_coeditor_code           HB7832
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1153
_journal_page_last               1157
_journal_paper_doi               10.1107/S2056989019009769
_journal_volume                  75
_journal_year                    2019
_chemical_formula_moiety         'C14 H8 F4 N2 O3'
_chemical_formula_sum            'C14 H8 F4 N2 O3'
_chemical_formula_weight         328.22
_chemical_name_common
(3a<i>R</i>,4<i>S</i>,7<i>R</i>,7a<i>S</i>)-2-[(Perfluoropyridin-4-yl)oxy]-3a,4,7,7a-tetrahydro-4,7-methanoisoindole-1,3-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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 93.44(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.285(6)
_cell_length_b                   5.945(3)
_cell_length_c                   17.888(8)
_cell_measurement_reflns_used    5752
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      30.4593
_cell_measurement_theta_min      3.3226
_cell_volume                     1304.1(11)
_computing_cell_refinement
;
SAINT (Bruker, 2017)
;
_computing_data_collection
;
APEX3 (Bruker, 2017)
;
_computing_data_reduction
;
SAINT (Bruker, 2017)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>, 2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'Omega Scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            18507
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         1.96
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2017)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.548
_exptl_crystal_size_mid          0.404
_exptl_crystal_size_min          0.355
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.250
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0563P)^2^+0.5528P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                3443
_reflns_number_total             3823
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7832sup1.cif
_cod_data_source_block           II
_cod_original_cell_volume        1304.1(10)
_cod_database_code               2243013
_cod_database_fobs_code          2243013
_shelx_hkl_checksum              36719
_shelx_res_checksum              77096