X-ray Structures of Cyclophanes Derived from Naphtho[1,2-c:5,6-c]difuran and the Synthesis, Structure, and Reaction Kinetics of Its 1,3,6,8-Tetrasilylated Derivative
Steven J. Robbins; Michelle E. Thibault; Jason D. Masuda; David R. Ward; René T. Boeré; Peter W. Dibble; Journal of Organic Chemistry 74 (2009) 5192–5198; doi:10.1021/jo900582r

data_4024665
_publ_contact_author_address
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Department of Chemistry and Biochemistry
University of Lethbridge
Lethbridge, AB Canada
T1K 3M4
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_publ_contact_author_email       dibble@uleth.ca
_publ_contact_author_fax         +1-403-329-2045
_publ_contact_author_name        'Dibble, Peter W.'
_publ_contact_author_phone       +1-403-329-2308
_publ_section_title
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X-ray Structures of Cyclophanes Derived from Naphtho[1,2-c:5,6-c]difuran
and the Synthesis, Structure, and Reaction Kinetics of Its
1,3,6,8-Tetrasilylated Derivative
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5192
_journal_page_last               5198
_journal_paper_doi               10.1021/jo900582r
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C23 H20 O6'
_chemical_formula_sum            'C23 H20 O6'
_chemical_formula_weight         392.39
_chemical_melting_point          673.15
_chemical_name_common            3C-acrylate-tethered-cyclophane
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2008-11-07 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.7520(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.2500(16)
_cell_length_b                   7.8987(9)
_cell_length_c                   16.1812(18)
_cell_measurement_reflns_used    4418
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.54
_cell_volume                     1812.1(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19966
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_correction_T_min  0.9044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS (Sheldrick, 2004) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4116
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0580
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0924P)^2^+0.3572P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1504
_refine_ls_wR_factor_ref         0.1766
_reflns_number_gt                2575
_reflns_number_total             4116
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900582r_si_004.cif
_cod_data_source_block           14
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4024665
_comment
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The aliphatic tether portion of this molecule exhibits disorder.
The primary chain (68%) is well behaved and refine well while two
of the atoms in the secondary chain (32%) exhibited additional disorder
which we were unable to model.  These atoms were left isotropic
which is a source of a few large U's as well as electron density
that is unaccounted for.
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