Synthesis and application of 3,4,7,8-tetrakis-exo-methylenecycloocta-1,5-diene as a versatile Diels-Alder diene: synthesis of V-shaped cyclooctatetraene fused acenes.
Gadigennavar, Savita; Sankararaman, Sethuraman; Organic & biomolecular chemistry 18 (2020) 6738–6744; doi:10.1039/d0ob01544j

data_7157658
_publ_section_title
;
 Synthesis and application of
 3,4,7,8-tetrakis-exo-methylenecycloocta-1,5-diene as a versatile
 Diels-Alder diene: synthesis of V-shaped cyclooctatetraene fused acenes.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6738
_journal_page_last               6744
_journal_paper_doi               10.1039/d0ob01544j
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         '2(C34 H30 N2 O6), H2O'
_chemical_formula_sum            'C68 H62 N4 O13'
_chemical_formula_weight         1143.21
_space_group_crystal_system      orthorhombic
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_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-07-22 deposited with the CCDC.	2020-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.741(4)
_cell_length_b                   13.765(2)
_cell_length_c                   21.012(3)
_cell_measurement_reflns_used    5667
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.30
_cell_measurement_theta_min      2.68
_cell_volume                     6288.2(17)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
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_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_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  0.0212
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.994
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_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11691
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        24.989
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_min         2.696
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       block
_exptl_crystal_F_000             2408
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details
;
 Flack x determined using 963 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2645
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0635
_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^)+(0.1150P)^2^+6.3671P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1733
_refine_ls_wR_factor_ref         0.1820
_reflns_Friedel_coverage         0.871
_reflns_Friedel_fraction_full    0.918
_reflns_Friedel_fraction_max     0.918
_reflns_number_gt                2302
_reflns_number_total             2645
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01544j2.cif
_cod_data_source_block           IMDPH
_cod_depositor_comments
'Adding full bibliography for 7157657--7157659.cif.'
_cod_original_cell_volume        6288.0(18)
_cod_database_code               7157658
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              25194