Revisiting indeno[1,2-b]fluorene by steric promoted synthesis while isolating the second stable 4nπ indeno[2,1-a]fluorene
Sharma, Himanshu; Bhardwaj, Nikhil; Das, Soumyajit; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01632J

data_7158905
_publ_section_title
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 Revisiting indeno[1,2-b]fluorene by steric promoted synthesis while
 isolating the second stable 4n\p indeno[2,1-a]fluorene
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01632J
_journal_year                    2022
_chemical_formula_moiety         'C35 H21 F5'
_chemical_formula_sum            'C35 H21 F5'
_chemical_formula_weight         536.52
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-13
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-09-07 deposited with the CCDC.	2022-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                117.393(3)
_cell_angle_beta                 111.710(3)
_cell_angle_gamma                93.822(3)
_cell_formula_units_Z            4
_cell_length_a                   13.8434(14)
_cell_length_b                   14.8766(13)
_cell_length_c                   16.0001(16)
_cell_measurement_reflns_used    9192
_cell_measurement_temperature    298
_cell_measurement_theta_max      23.95
_cell_measurement_theta_min      2.59
_cell_volume                     2603.7(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'BRUKER D8 VENTURE'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9906
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.768
_diffrn_reflns_theta_min         2.465
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1368 before and 0.0915 after correction.
The Ratio of minimum to maximum transmission is 0.7327.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic pinkish pink'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   pinkish
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.198
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.0048(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     729
_refine_ls_number_reflns         9906
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1234
_refine_ls_R_factor_gt           0.0619
_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^)+(0.0982P)^2^+0.6390P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1600
_refine_ls_wR_factor_ref         0.2111
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5612
_reflns_number_total             9906
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01632j2.cif
_cod_data_source_block           sdcf6_0m
_cod_original_cell_volume        2603.7(4)
_cod_database_code               7158905
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.440(2)
 0.560(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C69(H69), C34(H34), C66(H66), C50(H50), C30(H30), C15(H15), C31(H31),
 C12(H12), C65(H65), C47(H47), C28(H28), C63(H63), C44(H44), C45(H45), C29(H29),
  C9(H9), C64(H64), C46(H46), C10(H10), C23(H23), C11(H11), C59(H59), C21(H21),
 C56(H56)
3.b Idealised Me refined as rotating group:
 C61(H61A,H61B,H61C), C26(H26A,H26B,H26C), C20(H20A,H20B,H20C), C58(H58A,H58B,
 H58C), C55(H55A,H55B,H55C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              61181
_olex2_submission_special_instructions 'No special instructions were received'