Substrate-dependent reaction of 1-aryl-2-alkyl-1,2-diketones with 2-aroyl-1-chlorocyclopropanecarboxylates: selective access to 2ʹ,5ʹ-dicyclopropoxy-1,1ʹ:4ʹ,1ʺ-teraryls and pentafulvenes
Prakash, Meher; Rani, Poonam; Samanta, Sampak; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00971D

data_7158771
_publ_section_title
;
 Substrate-dependent reaction of 1-aryl-2-alkyl-1,2-diketones with
 2-aroyl-1-chlorocyclopropanecarboxylates: selective access to
 2&#x02B9;,5&#x02B9;-dicyclopropoxy-1,1&#x02B9;:4&#x02B9;,1&#x02BA;-teraryls
 and pentafulvenes
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00971D
_journal_year                    2022
_chemical_formula_moiety         'C21 H19 O4 S'
_chemical_formula_sum            'C21 H19 O4 S'
_chemical_formula_weight         367.42
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-09-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_audit_update_record
;
2022-04-28 deposited with the CCDC.	2022-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                86.390(2)
_cell_angle_beta                 79.605(2)
_cell_angle_gamma                66.426(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6775(6)
_cell_length_b                   9.7016(6)
_cell_length_c                   11.8817(8)
_cell_measurement_reflns_used    6757
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.68
_cell_volume                     901.70(10)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20304
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.319
_diffrn_reflns_theta_min         2.291
_exptl_absorpt_coefficient_mu    0.203
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       block
_exptl_crystal_F_000             386
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.6
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4474
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0559P)^2^+0.3597P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1084
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3976
_reflns_number_total             4474
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00971d2.cif
_cod_data_source_block           22julb_0m
_cod_database_code               7158771
_shelx_shelxl_version_number     2018/3
_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
2.a Ternary CH refined with riding coordinates:
 C00L(H00L)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00B,H00C), C00J(H00D,H00E)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00G(H00G), C00H(H00H), C00K(H00K), C00M(H00M), C00O(H00O),
 C00P(H00P)
2.d Idealised Me refined as rotating group:
 C00N(H00F,H00I,H00J), C00Q(H00N,H00Q,H00R)
;
_shelx_res_checksum              8197
_olex2_submission_special_instructions 'No special instructions were received'