One-Pot Synthesis of Polysubstituted Spirofluorene-Indene via Ru(II)-Catalyzed [3 + 2] Annulation and Intramolecular Friedel-Crafts Cyclization.
Zhu, Yu-Qin; Dong, Lin; The Journal of organic chemistry 80 (2015) 9973–9979; doi:10.1021/acs.joc.5b01517

data_4031560
_publ_section_title
;
 One-Pot Synthesis of Polysubstituted Spirofluorene-Indene via
 Ru(II)-Catalyzed [3 + 2] Annulation and Intramolecular Friedel-Crafts
 Cyclization.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9973
_journal_page_last               9979
_journal_paper_doi               10.1021/acs.joc.5b01517
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C34 H24'
_chemical_formula_sum            'C34 H24'
_chemical_formula_weight         432.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-14
_audit_creation_method
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Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
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_cell_angle_alpha                90.00
_cell_angle_beta                 92.330(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4443(4)
_cell_length_b                   17.7411(8)
_cell_length_c                   12.8612(7)
_cell_measurement_reflns_used    2486
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4168
_cell_measurement_theta_min      3.1641
_cell_volume                     2381.12(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0499698000
_diffrn_orient_matrix_UB_12      -0.0262847000
_diffrn_orient_matrix_UB_13      0.0073002000
_diffrn_orient_matrix_UB_21      0.0051334000
_diffrn_orient_matrix_UB_22      -0.0127065000
_diffrn_orient_matrix_UB_23      -0.0519603000
_diffrn_orient_matrix_UB_31      0.0457556000
_diffrn_orient_matrix_UB_32      -0.0273312000
_diffrn_orient_matrix_UB_33      0.0171351000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9548
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.17
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0507P)^2^+0.2895P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1187
_reflns_number_gt                3197
_reflns_number_total             4352
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01517_si_001.cif
_cod_data_source_block           150113_zyq12010
_cod_depositor_comments          'Adding full bibliography for 4031560.cif.'
_cod_original_cell_volume        2381.13(19)
_cod_database_code               4031560
_chemical_oxdiff_formula         'c10 h10 n2 o8 p1'
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13),
 C15(H15), C16(H16), C18(H18), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27),
  C29(H29), C30(H30), C31(H31), C32(H32), C33(H33)
2.b Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C)
;