Regio- and diastereoselective synthesis of diverse spirocyclic indenes by cyclization with indene-dienes as two carbon building blocks.
Deng, Yi-Hang; Xu, Wen-Li; Wang, Lei; Tang, Cheng-Yang; Fu, Ji-Ya; Zhang, Chuan-Bao; Organic & biomolecular chemistry 21 (2023) 6681–6686; doi:10.1039/d3ob00982c

data_7159498
_publ_section_title
;
 Regio- and diastereoselective synthesis of diverse spirocyclic indenes by
 cyclization with indene-dienes as two carbon building blocks.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6681
_journal_page_last               6686
_journal_paper_doi               10.1039/d3ob00982c
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C40 H37 Cl N2 O2'
_chemical_formula_sum            'C40 H37 Cl N2 O2'
_chemical_formula_weight         613.16
_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             2023-06-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-06-19 deposited with the CCDC.	2023-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.730(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.946(5)
_cell_length_b                   32.16(2)
_cell_length_c                   11.104(6)
_cell_measurement_reflns_used    1424
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.087
_cell_measurement_theta_min      2.334
_cell_volume                     3322(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      296
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Helios multilayer optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2271
_diffrn_reflns_av_unetI/netI     0.2093
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            26901
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.061
_diffrn_source_type              Microfocus
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.2627
_exptl_absorpt_correction_T_min  0.1802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1328 before and 0.0903 after correction. The Ratio of minimum to maximum transmission is 0.6860. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'light orange'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.076
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.0042(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   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     414
_refine_ls_number_reflns         6529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.2231
_refine_ls_R_factor_gt           0.0863
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0956P)^2^+0.1769P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1941
_refine_ls_wR_factor_ref         0.2777
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2604
_reflns_number_total             6529
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00982c2.cif
_cod_data_source_block           m11265_0m
_cod_depositor_comments
;
Adding full bibliography for 7159497--7159499.cif.

2025-03-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C160 H148 Cl4 N8 O8'
_cod_original_formula_weight         2452.66
_cod_original_formula_moiety         '4(C40 H37 Cl N2 O2)'
_cod_original_formula_units_Z            1
_cod_database_code               7159498
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.976
_diffrn_source_source            'Incoatc Ius 3.0 '
_olex2_refinement_description
;
1. 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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C28(H28), C00A(H00A), C20(H20), C17(H17), C18(H18), C19(H19), C26(H26),
 C23(H23), C22(H22), C5(H5), C24(H24), C2(H2A), C6(H6), C1(H1)
2.d Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C33(H33A,H33B,
 H33C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              76176
_olex2_submission_special_instructions 'No special instructions were received'