Synthesis of carbonyl-bridged dibenzofulvalenes and related compounds by rhodium-catalyzed stitching reaction.
Shintani, Ryo; Kishikawa, Shinnosuke; Nakamura, Kimihiro; Tsuda, Tomohiro; Nozaki, Kyoko; Chemical communications (Cambridge, England)  (2019) –; doi:10.1039/c8cc09943j

data_7122768
_publ_section_title
;
 Synthesis of carbonyl-bridged dibenzofulvalenes and related compounds by
 rhodium-catalyzed stitching reaction.
;
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/c8cc09943j
_journal_year                    2019
_chemical_formula_moiety         'C26 H28 Ge'
_chemical_formula_sum            'C26 H28 Ge'
_chemical_formula_weight         413.07
_chemical_name_systematic        Ge
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-08 deposited with the CCDC.
2018-12-28 downloaded from the CCDC.
;
_cell_angle_alpha                100.752(2)
_cell_angle_beta                 100.803(2)
_cell_angle_gamma                119.398(4)
_cell_formula_units_Z            8
_cell_length_a                   16.8701(6)
_cell_length_b                   16.9405(6)
_cell_length_c                   18.3624(3)
_cell_measurement_reflns_used    10593
_cell_measurement_temperature    113
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     4246.4(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      113
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.759
_diffrn_measurement_device_type  'XTalAB P200'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.056
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.904
_diffrn_reflns_Laue_measured_fraction_max 0.759
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            18557
_diffrn_reflns_point_group_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.759
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.599
_diffrn_reflns_theta_min         1.835
_exptl_absorpt_coefficient_mu    1.450
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Rigaku Pilatus 200K'
_exptl_crystal_colour            'clear orangish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_recrystallization_method
'An orange hot hexane solution of the compound  was prepared. Crystals suitable for X-rayanalysis were obtained by cooling the solution at room temperature.'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1019
_refine_ls_number_reflns         18557
_refine_ls_number_restraints     62
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0297
_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^)+(0.0342P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0630
_refine_ls_wR_factor_ref         0.0648
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14319
_reflns_number_total             18557
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc09943j2.cif
_cod_data_source_block           nsk1129a_twin1_hklf4
_cod_database_code               7122768
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.760
_shelx_estimated_absorpt_t_min   0.670
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5472(5)
 0.4528(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C00Z-C02X \\sim C00Z-C0AA
 with sigma of 0.02
 C00Z-C030 \\sim C00Z-C0
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
C00Z \\sim C02X \\sim C030 \\sim C0AA \\sim C0: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.01
5. Rigid body (RIGU) restrains
 C00Z, C02X, C030, C0AA, C0
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(H00A)=Sof(C0AA)=Sof(H0AA)=Sof(H0AB)=Sof(H0AC)=Sof(C0)=Sof(H0A)=Sof(H0B)=
 Sof(H0C)=1-FVAR(1)
 Sof(H00Z)=Sof(C02X)=Sof(H02K)=Sof(H02L)=Sof(H02M)=Sof(C030)=Sof(H03A)=
 Sof(H03B)=Sof(H03C)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C00J(H00J), C00W(H00W), C00Z(H00Z), C00Z(H00A), C010(H010), C01N(H01N),
 C01S(H01S), C026(H026), C02G(H9AA)
7.b Aromatic/amide H refined with riding coordinates:
 C00F(H00H), C00L(H00L), C00R(H00R), C00S(H00S), C00U(H00U), C012(H012),
 C014(H014), C018(H018), C01B(H01B), C01E(H01E), C01F(H01F), C01G(H01K),
 C01H(H01H), C01M(H01M), C01T(H01T), C01U(H01U), C01V(H01V), C01W(H01W),
 C01X(H01X), C01Y(H01Y), C021(H021), C022(H022), C02A(H02N), C02C(H02O),
 C02E(H02P), C02F(H02Q), C02H(H02J), C02J(H02X), C02K(H0BA), C02R(H02R),
 C02T(H02T), C02W(H02W)
7.c Idealised Me refined as rotating group:
 C00N(H00B,H00C,H00D), C00Y(H00E,H00F,H00G), C01C(H01A,H01C,H01D), C01D(H01G,
 H01I,H01J), C023(H7AA,H,HA), C025(H02A,H02B,H02C), C027(H8AA,HB,HC), C028(H1AA,
 HD,HE), C029(H02D,H02E,H02F), C02B(H2AA,HF,HG), C02D(H02G,H02H,H02I),
 C02I(H02S,H02U,H02V), C02L(H3AA,HH,HI), C02M(H02Y,HJ,HK), C02N(H1BA,HL,HM),
 C02O(H4AA,HN,HO), C02P(H02Z,HP,HQ), C02Q(H5AA,HR,HS), C02U(H6AA,HT,HU),
 C02V(H2BA,HV,HW), C02X(H02K,H02L,H02M), C02Y(H3BA,HX,HY), C02Z(H02,HZ,H4BA),
 C030(H03A,H03B,H03C), C0AA(H0AA,H0AB,H0AC), C0(H0A,H0B,H0C)
;
_shelx_res_checksum              57243
_olex2_submission_original_sample_id NSK1129
_olex2_submission_special_instructions 'No special instructions were received'