An Oxidative Macrobicyclic Ring Opening of a Triptycene to a Highly Functionalized Fluorene Derivative.
Baumgärtner, Kevin; Rominger, Frank; Mastalerz, Michael; The Journal of organic chemistry 80 (2015) 8881–8886; doi:10.1021/acs.joc.5b01426

data_4036292
_publ_section_title
;
 An Oxidative Macrobicyclic Ring Opening of a Triptycene to a Highly
 Functionalized Fluorene Derivative.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8881
_journal_page_last               8886
_journal_paper_doi               10.1021/acs.joc.5b01426
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C36.5 H43.5 Cl1.5 N O9'
_chemical_formula_weight         693.40
_chemical_name_common            '4d in manuscript'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.7517(11)
_cell_length_b                   22.499(3)
_cell_length_c                   32.974(4)
_cell_measurement_reflns_used    8301
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      21.37
_cell_measurement_theta_min      2.19
_cell_volume                     7234.6(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1055
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            60349
_diffrn_reflns_point_group_measured_fraction_full 0.892
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        21.034
_diffrn_reflns_theta_max         21.034
_diffrn_reflns_theta_min         0.905
_diffrn_source                   'ImuS microsource'
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.9565
_exptl_absorpt_correction_T_min  0.7642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). <i>SADABS</i>. University of G\"ottingen, Germany.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       plate
_exptl_crystal_F_000             2936
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
; 
 Flack x determined using 1760 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.53(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     995
_refine_ls_number_reflns         6965
_refine_ls_number_restraints     1031
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0771
_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^)+(0.1276P)^2^+10.5372P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2004
_refine_ls_wR_factor_ref         0.2191
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_full    0.780
_reflns_Friedel_fraction_max     0.780
_reflns_number_gt                5448
_reflns_number_total             6965
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01426_si_002.cif
_cod_data_source_block           kba6
_cod_original_cell_volume        7234.7(14)
_cod_original_formula_sum        'C36.50 H43.50 Cl1.50 N O9'
_cod_database_code               4036292
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.940
_shelx_estimated_absorpt_t_max   0.994
_shelx_res_checksum              12650
_shelx_hkl_checksum              51680