La(OTf)<sub>3</sub> facilitated self-condensation of 2-indolylmethanol: construction of highly substituted indeno[1,2-<i>b</i>]indoles.
Tang, Zhicong; Hong, Gang; Hu, Chen; Wang, Qi; Zhong, Yi; Gong, Yu; Yang, Peng; Wang, Limin; Organic & biomolecular chemistry 19 (2021) 10337–10342; doi:10.1039/d1ob01517f

data_7158315
_publ_section_title
;
 La(OTf)<sub>3</sub> facilitated self-condensation of 2-indolylmethanol:
 construction of highly substituted indeno[1,2-<i>b</i>]indoles.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10337
_journal_page_last               10342
_journal_paper_doi               10.1039/d1ob01517f
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C H2 Cl2, C42 H28 Cl2 N2'
_chemical_formula_sum            'C43 H30 Cl4 N2'
_chemical_formula_weight         716.49
_chemical_melting_point          452(7)
_chemical_name_systematic
(S)-6-(2-benzhydryl-5-chloro-1H-indol-3-yl)-2-chloro-6-phenyl-5,6-dihydroindeno[2,1-b]indole
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-10 deposited with the CCDC.	2021-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.3160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9191(4)
_cell_length_b                   12.8360(4)
_cell_length_c                   20.3504(6)
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      54.98
_cell_measurement_theta_min      4.16
_cell_volume                     3489.49(18)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      193
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            30275
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.966
_diffrn_reflns_theta_min         2.996
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.186
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1327 before and 0.0795 after correction. The Ratio of minimum to maximum transmission is 0.7184. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             1480
_exptl_crystal_preparation       fluorescence
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/n-hexane=1:1'
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.722
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         6596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0592P)^2^+2.4121P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1325
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5690
_reflns_number_total             6596
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01517f2.cif
_cod_data_source_block           mj21120_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '445-458' was changed to
'452(7)' -- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7158315--7158316.cif.
;
_cod_database_code               7158315
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.899
_shelx_estimated_absorpt_t_min   0.862
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3), C15(H15), C17(H17), C18(H18), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31),
  C33(H33), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39),
 C40(H40), C41(H41), C42(H42), C43(H43)
;
_shelx_res_checksum              92026
_olex2_submission_special_instructions 'No special instructions were received'