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_7158770
_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         'C19 H17 Br O4'
_chemical_formula_sum            'C19 H17 Br O4'
_chemical_formula_weight         389.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-04-28 deposited with the CCDC.	2022-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                90(4)
_cell_angle_beta                 79.975(4)
_cell_angle_gamma                90(4)
_cell_formula_units_Z            4
_cell_length_a                   8.8846(3)
_cell_length_b                   10.4690(6)
_cell_length_c                   18.3384(9)
_cell_measurement_reflns_used    7685
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5250
_cell_measurement_theta_min      3.3510
_cell_volume                     1679.66(14)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19410
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.130
_diffrn_reflns_theta_min         2.979
_exptl_absorpt_coefficient_mu    2.467
_exptl_absorpt_correction_T_max  35
_exptl_absorpt_correction_T_min  25
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_description       Block
_exptl_crystal_F_000             792
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0542(17)
_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   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         4138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0390P)^2^+0.4901P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0874
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3264
_reflns_number_total             4138
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00971d2.cif
_cod_data_source_block           ss24
_cod_database_code               7158770
_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 Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00B), C00L(H00E,H00G), C00M(H00I,H00J), C00N(H00K,H00L)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00C(H00C), C00D(H00D), C00F(H00F), C00H(H00H)
2.c Idealised Me refined as rotating group:
 C00O(H00M,H00N,H00O)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              67749
_olex2_submission_special_instructions 'No special instructions were received'