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#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/76/7217624.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7217624
loop_
_publ_author_name
'Reddy, Chennakesava'
'Srinivasarao, Arulananda Babu'
'Aslam, Nayyar Ahmad'
_publ_section_title
;
 Indium-assisted aluminium-based stereoselective allylation of
 prostereogenic α, α-disubstituted cycloalkanones and imines
;
_journal_name_full               'RSC Advances'
_journal_paper_doi               10.1039/C4RA04293J
_journal_year                    2014
_chemical_formula_moiety         'C19 H24 Cl2 O3'
_chemical_formula_sum            'C19 H24 Cl2 O3'
_chemical_formula_weight         371.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-01-03T23:53:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                61.212(2)
_cell_angle_beta                 66.057(2)
_cell_angle_gamma                71.403(3)
_cell_formula_units_Z            2
_cell_length_a                   9.5268(4)
_cell_length_b                   11.1801(6)
_cell_length_c                   11.2526(5)
_cell_measurement_reflns_used    4758
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.485
_cell_measurement_theta_min      2.168
_cell_volume                     948.53(8)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11741
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.1
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        R(int) was 0.0472 before and 0.0388 after correction.
        The Ratio of minimum to maximum transmission is 0.9173.
        The λ/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.3
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3336
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0460P)²+0.3658P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1171
_reflns_number_gt                2371
_reflns_number_total             3336
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra04293j2.cif
_cod_data_source_block           sci216_cr720a_0m
_cod_database_code               7217624
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 1.07826(11) 0.30434(9) 0.11167(8) 0.0909(3) Uani 1 1 d .
Cl2 Cl 1.18089(8) 0.24421(10) 0.56964(8) 0.0831(3) Uani 1 1 d .
O1 O 0.52195(18) 0.32961(16) 0.73355(19) 0.0589(5) Uani 1 1 d .
O2 O 0.73850(17) 0.01187(15) 1.04751(17) 0.0523(4) Uani 1 1 d .
H2 H 0.6577 -0.013 1.0644 0.078 Uiso 1 1 calc R
O3 O 0.55376(19) 0.10032(17) 0.83257(19) 0.0597(5) Uani 1 1 d .
C1 C 1.0214(3) 0.2463(3) 0.2957(3) 0.0554(6) Uani 1 1 d .
C2 C 1.1090(3) 0.2640(3) 0.3558(3) 0.0556(6) Uani 1 1 d .
H2A H 1.1979 0.3053 0.2991 0.067 Uiso 1 1 calc R
C3 C 1.0630(3) 0.2196(3) 0.5014(3) 0.0504(6) Uani 1 1 d .
C4 C 0.9305(2) 0.1578(2) 0.5915(2) 0.0458(6) Uani 1 1 d .
C5 C 0.8795(3) 0.1086(2) 0.7507(2) 0.0509(6) Uani 1 1 d .
H5A H 0.9689 0.093 0.78 0.061 Uiso 1 1 calc R
H5B H 0.8436 0.0206 0.7937 0.061 Uiso 1 1 calc R
C6 C 0.7484(2) 0.2094(2) 0.8095(2) 0.0407(5) Uani 1 1 d .
C7 C 0.6004(3) 0.2061(2) 0.7926(2) 0.0443(5) Uani 1 1 d .
C8 C 0.3748(3) 0.3305(3) 0.7219(4) 0.0784(9) Uani 1 1 d .
H8A H 0.3098 0.2758 0.814 0.094 Uiso 1 1 calc R
H8B H 0.3931 0.2913 0.6556 0.094 Uiso 1 1 calc R
C9 C 0.2979(4) 0.4738(3) 0.6714(4) 0.1030(12) Uani 1 1 d .
H9A H 0.2718 0.509 0.7418 0.154 Uiso 1 1 calc R
H9B H 0.2048 0.4778 0.655 0.154 Uiso 1 1 calc R
H9C H 0.3665 0.5287 0.5842 0.154 Uiso 1 1 calc R
C10 C 0.7944(3) 0.3531(2) 0.7467(2) 0.0493(6) Uani 1 1 d .
H10A H 0.8663 0.3743 0.6512 0.059 Uiso 1 1 calc R
H10B H 0.7032 0.4238 0.7428 0.059 Uiso 1 1 calc R
C11 C 0.8719(3) 0.3463(3) 0.8468(3) 0.0641(7) Uani 1 1 d .
H11A H 0.98 0.3583 0.7968 0.077 Uiso 1 1 calc R
H11B H 0.8192 0.4185 0.8814 0.077 Uiso 1 1 calc R
C12 C 0.8596(3) 0.2050(2) 0.9698(3) 0.0530(6) Uani 1 1 d .
H12A H 0.8393 0.2112 1.0585 0.064 Uiso 1 1 calc R
H12B H 0.955 0.1414 0.9541 0.064 Uiso 1 1 calc R
C13 C 0.7247(2) 0.1574(2) 0.9735(2) 0.0419(5) Uani 1 1 d .
C14 C 0.5655(2) 0.2283(2) 1.0426(2) 0.0470(6) Uani 1 1 d .
H14A H 0.5498 0.3241 0.977 0.056 Uiso 1 1 calc R
H14B H 0.4846 0.1846 1.0549 0.056 Uiso 1 1 calc R
C15 C 0.5455(3) 0.2246(3) 1.1836(3) 0.0519(6) Uani 1 1 d .
C16 C 0.5304(4) 0.0911(3) 1.3085(3) 0.0958(11) Uani 1 1 d .
H16A H 0.5074 0.1051 1.3927 0.144 Uiso 1 1 calc R
H16B H 0.6261 0.0287 1.2966 0.144 Uiso 1 1 calc R
H16C H 0.4479 0.0528 1.3174 0.144 Uiso 1 1 calc R
C17 C 0.5392(3) 0.3379(3) 1.1961(3) 0.0735(8) Uani 1 1 d .
H17A H 0.525 0.3342 1.2845 0.088 Uiso 1 1 calc R
H17B H 0.5489 0.4214 1.1165 0.088 Uiso 1 1 calc R
C18 C 0.8480(3) 0.1409(2) 0.5243(3) 0.0547(6) Uani 1 1 d .
H18 H 0.7597 0.0986 0.5802 0.066 Uiso 1 1 calc R
C19 C 0.8910(3) 0.1839(3) 0.3791(3) 0.0587(7) Uani 1 1 d .
H19 H 0.8328 0.1709 0.3381 0.07 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 O1 C8 116.23(19)
C13 O2 H2 109.5
C2 C1 Cl1 118.9(2)
C2 C1 C19 120.8(2)
C19 C1 Cl1 120.3(2)
C1 C2 H2A 120.5
C1 C2 C3 118.9(2)
C3 C2 H2A 120.5
C2 C3 Cl2 116.19(18)
C2 C3 C4 123.0(2)
C4 C3 Cl2 120.80(19)
C3 C4 C5 123.4(2)
C18 C4 C3 115.3(2)
C18 C4 C5 121.2(2)
C4 C5 H5A 108.6
C4 C5 H5B 108.6
C4 C5 C6 114.64(18)
H5A C5 H5B 107.6
C6 C5 H5A 108.6
C6 C5 H5B 108.6
C5 C6 C13 109.41(17)
C7 C6 C5 107.38(18)
C7 C6 C10 116.36(18)
C7 C6 C13 108.65(16)
C10 C6 C5 112.54(17)
C10 C6 C13 102.23(17)
O1 C7 C6 114.69(19)
O3 C7 O1 122.1(2)
O3 C7 C6 123.2(2)
O1 C8 H8A 110.1
O1 C8 H8B 110.1
O1 C8 C9 108.0(2)
H8A C8 H8B 108.4
C9 C8 H8A 110.1
C9 C8 H8B 110.1
C8 C9 H9A 109.5
C8 C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9B 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C6 C10 H10A 110.5
C6 C10 H10B 110.5
H10A C10 H10B 108.7
C11 C10 C6 106.07(19)
C11 C10 H10A 110.5
C11 C10 H10B 110.5
C10 C11 H11A 110.4
C10 C11 H11B 110.4
H11A C11 H11B 108.6
C12 C11 C10 106.85(19)
C12 C11 H11A 110.4
C12 C11 H11B 110.4
C11 C12 H12A 110.7
C11 C12 H12B 110.7
C11 C12 C13 105.20(19)
H12A C12 H12B 108.8
C13 C12 H12A 110.7
C13 C12 H12B 110.7
O2 C13 C6 113.38(17)
O2 C13 C12 108.92(18)
O2 C13 C14 110.93(17)
C12 C13 C6 101.91(17)
C12 C13 C14 111.87(18)
C14 C13 C6 109.55(17)
C13 C14 H14A 108.3
C13 C14 H14B 108.3
H14A C14 H14B 107.4
C15 C14 C13 115.91(19)
C15 C14 H14A 108.3
C15 C14 H14B 108.3
C16 C15 C14 118.1(2)
C17 C15 C14 121.0(2)
C17 C15 C16 120.9(3)
C15 C16 H16A 109.5
C15 C16 H16B 109.5
C15 C16 H16C 109.5
H16A C16 H16B 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C15 C17 H17A 120
C15 C17 H17B 120
H17A C17 H17B 120
C4 C18 H18 118.5
C19 C18 C4 123.1(2)
C19 C18 H18 118.5
C1 C19 C18 118.9(2)
C1 C19 H19 120.6
C18 C19 H19 120.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.739(3)
Cl2 C3 1.739(2)
O1 C7 1.329(3)
O1 C8 1.456(3)
O2 H2 0.82
O2 C13 1.416(2)
O3 C7 1.208(3)
C1 C2 1.373(3)
C1 C19 1.373(3)
C2 H2A 0.93
C2 C3 1.377(3)
C3 C4 1.393(3)
C4 C5 1.505(3)
C4 C18 1.392(3)
C5 H5A 0.97
C5 H5B 0.97
C5 C6 1.555(3)
C6 C7 1.512(3)
C6 C10 1.541(3)
C6 C13 1.583(3)
C8 H8A 0.97
C8 H8B 0.97
C8 C9 1.463(4)
C9 H9A 0.96
C9 H9B 0.96
C9 H9C 0.96
C10 H10A 0.97
C10 H10B 0.97
C10 C11 1.541(3)
C11 H11A 0.97
C11 H11B 0.97
C11 C12 1.519(3)
C12 H12A 0.97
C12 H12B 0.97
C12 C13 1.519(3)
C13 C14 1.550(3)
C14 H14A 0.97
C14 H14B 0.97
C14 C15 1.500(3)
C15 C16 1.475(4)
C15 C17 1.320(4)
C16 H16A 0.96
C16 H16B 0.96
C16 H16C 0.96
C17 H17A 0.93
C17 H17B 0.93
C18 H18 0.93
C18 C19 1.377(3)
C19 H19 0.93
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139199019
