Selective synthesis of unsymmetric dibenzo[a,e]pentalenes by a rhodium-catalysed stitching reaction.
Takahashi, Keisuke; Ito, Shingo; Shintani, Ryo; Nozaki, Kyoko; Chemical science 8 (2017) 101–107; doi:10.1039/c6sc04560j

data_1544556
_publ_section_title
;
 Selective synthesis of unsymmetric dibenzo[a,e]pentalenes by a
 rhodium-catalysed stitching reaction.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              101
_journal_page_last               107
_journal_paper_doi               10.1039/c6sc04560j
_journal_volume                  8
_journal_year                    2017
_chemical_formula_moiety         'C27 H36 N2 O2 Si2'
_chemical_formula_sum            'C27 H36 N2 O2 Si2'
_chemical_formula_weight         476.76
_chemical_melting_point          458.0(10)
_chemical_name_systematic
5-(tert-Butyldimethylsilyl)-3-(dimethylamino)-8-nitro-10-(trimethylsilyl)dibenzo[a,e]pentalene
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2016-10-27 deposited with the CCDC.
2016-11-03 downloaded from the CCDC.
;
_cell_angle_alpha                110.915(10)
_cell_angle_beta                 93.663(16)
_cell_angle_gamma                94.99(2)
_cell_formula_units_Z            2
_cell_length_a                   7.221(3)
_cell_length_b                   11.790(5)
_cell_length_c                   16.389(9)
_cell_measurement_reflns_used    3326
_cell_measurement_temperature    93
_cell_measurement_theta_max      31.0
_cell_measurement_theta_min      2.7
_cell_volume                     1291.6(11)
_computing_cell_refinement       'RIGAKU CrystalClear'
_computing_data_collection       'RIGAKU CrystalClear'
_computing_data_reduction        'RIGAKU CrystalClear'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto, et al.)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_unetI/netI     0.1151
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9281
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         1.855
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             512
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/methanol'
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.843
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.140
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4927
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1298
_refine_ls_R_factor_gt           0.0765
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1050P)^2^+0.7445P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1805
_refine_ls_wR_factor_ref         0.2282
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3057
_reflns_number_total             4927
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc04560j2.cif
_cod_data_source_block           ANPh2Pen
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '457--459' was changed to '458.0(10)'
- the average value was taken and precision was estimated.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1544554--1544556.cif.

 Adding full bibliography for 1544554--1544556.cif.
;
_cod_original_cell_volume        1291.6(10)
_cod_database_code               1544556
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.998
_shelxl_version_number           2014/6
_shelx_res_checksum              2726