#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/72/7117229.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_7117229
loop_
_publ_author_name
'Subrata Mukherjee'
'Santigopal Mondal'
'Atanu Patra'
'Rajesh G. Gonnade'
'Akkattu T. Biju'
_publ_section_title
;
 N-Heterocyclic carbene-catalyzed diastereoselective synthesis of
 beta-lactone-fused cyclopentanes using homoenolate annulation reaction
;
_journal_name_full               Chem.Commun.
_journal_page_first              9559
_journal_paper_doi               10.1039/C5cc02960K
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C23 H19 N O3, C H Cl3'
_chemical_formula_sum            'C24 H20 Cl3 N O3'
_chemical_formula_weight         476.76
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-04-01 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.471(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.3285(8)
_cell_length_b                   11.4221(6)
_cell_length_c                   12.7961(6)
_cell_measurement_reflns_used    8328
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      29.26
_cell_measurement_theta_min      2.23
_cell_volume                     2230.2(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13651
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.438
_exptl_absorpt_correction_T_max  0.8514
_exptl_absorpt_correction_T_min  0.8208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.38
_refine_diff_density_max         1.141
_refine_diff_density_min         -0.993
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0661
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0327P)²+8.4930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.1618
_reflns_number_gt                3515
_reflns_number_total             3914
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc02960k2.cif
_cod_data_source_block           sb_8
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7117229
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.95833(16) 0.1120(2) 0.3081(2) 0.0193(6) Uani 1 1 d . . .
O2 O 0.98251(18) 0.2119(2) 0.4634(2) 0.0266(6) Uani 1 1 d . . .
O3 O 0.69646(16) 0.0419(2) 0.23233(19) 0.0188(6) Uani 1 1 d . . .
N1 N 0.75156(19) -0.0457(3) 0.2431(2) 0.0144(6) Uani 1 1 d . . .
C1 C 0.8372(2) 0.1787(3) 0.3546(3) 0.0142(7) Uani 1 1 d . . .
H1 H 0.7987 0.1386 0.4023 0.017 Uiso 1 1 calc R . .
C2 C 0.9341(2) 0.1774(3) 0.3919(3) 0.0180(8) Uani 1 1 d . . .
C3 C 0.8650(2) 0.1020(3) 0.2636(3) 0.0153(7) Uani 1 1 d . . .
C4 C 0.8490(2) 0.1720(3) 0.1621(3) 0.0165(8) Uani 1 1 d . . .
H4A H 0.7945 0.1460 0.1209 0.020 Uiso 1 1 calc R . .
H4B H 0.8986 0.1630 0.1185 0.020 Uiso 1 1 calc R . .
C5 C 0.8408(2) 0.3002(3) 0.1983(3) 0.0161(8) Uani 1 1 d . . .
H5 H 0.9011 0.3333 0.2130 0.019 Uiso 1 1 calc R . .
C6 C 0.7987(2) 0.2916(3) 0.3033(3) 0.0159(7) Uani 1 1 d . . .
H6 H 0.7347 0.2770 0.2850 0.019 Uiso 1 1 calc R . .
C7 C 0.8391(2) -0.0242(3) 0.2604(3) 0.0138(7) Uani 1 1 d . . .
C8 C 0.8971(2) -0.1172(3) 0.2751(3) 0.0174(8) Uani 1 1 d . . .
H8 H 0.9581 -0.1021 0.2884 0.021 Uiso 1 1 calc R . .
C9 C 0.8672(3) -0.2317(3) 0.2705(3) 0.0209(8) Uani 1 1 d . . .
H9 H 0.9071 -0.2954 0.2792 0.025 Uiso 1 1 calc R . .
C10 C 0.7780(3) -0.2512(3) 0.2531(3) 0.0201(8) Uani 1 1 d . . .
H10 H 0.7558 -0.3289 0.2505 0.024 Uiso 1 1 calc R . .
C11 C 0.7215(2) -0.1579(3) 0.2395(3) 0.0179(8) Uani 1 1 d . . .
H11 H 0.6602 -0.1719 0.2274 0.021 Uiso 1 1 calc R . .
C12 C 0.7891(2) 0.3799(3) 0.1205(3) 0.0172(8) Uani 1 1 d . . .
C13 C 0.7045(3) 0.3491(4) 0.0806(3) 0.0233(9) Uani 1 1 d . . .
H13 H 0.6806 0.2762 0.0995 0.028 Uiso 1 1 calc R . .
C14 C 0.6548(3) 0.4246(4) 0.0131(3) 0.0336(11) Uani 1 1 d . . .
H14 H 0.5968 0.4037 -0.0131 0.040 Uiso 1 1 calc R . .
C15 C 0.6894(3) 0.5290(4) -0.0154(3) 0.0360(11) Uani 1 1 d . . .
H15 H 0.6551 0.5802 -0.0611 0.043 Uiso 1 1 calc R . .
C16 C 0.7729(3) 0.5604(4) 0.0209(3) 0.0349(11) Uani 1 1 d . . .
H16 H 0.7966 0.6324 -0.0006 0.042 Uiso 1 1 calc R . .
C17 C 0.8237(3) 0.4861(3) 0.0902(3) 0.0251(9) Uani 1 1 d . . .
H17 H 0.8815 0.5082 0.1162 0.030 Uiso 1 1 calc R . .
C18 C 0.8060(2) 0.4002(3) 0.3714(3) 0.0153(7) Uani 1 1 d . . .
C19 C 0.7322(3) 0.4423(3) 0.4143(3) 0.0219(8) Uani 1 1 d . . .
H19 H 0.6775 0.4037 0.4000 0.026 Uiso 1 1 calc R . .
C20 C 0.7384(3) 0.5422(4) 0.4791(3) 0.0274(9) Uani 1 1 d . . .
H20 H 0.6879 0.5713 0.5080 0.033 Uiso 1 1 calc R . .
C21 C 0.8175(3) 0.5973(3) 0.5005(3) 0.0259(9) Uani 1 1 d . . .
H21 H 0.8215 0.6644 0.5445 0.031 Uiso 1 1 calc R . .
C22 C 0.8911(3) 0.5568(3) 0.4589(3) 0.0235(9) Uani 1 1 d . . .
H22 H 0.9458 0.5952 0.4745 0.028 Uiso 1 1 calc R . .
C23 C 0.8851(3) 0.4586(3) 0.3936(3) 0.0196(8) Uani 1 1 d . . .
H23 H 0.9358 0.4314 0.3638 0.024 Uiso 1 1 calc R . .
Cl1 Cl 0.43671(7) 0.07997(10) 0.30089(10) 0.0386(3) Uani 1 1 d . A .
Cl2 Cl 0.52876(8) 0.29201(11) 0.25821(17) 0.0704(6) Uani 1 1 d . A .
Cl3' Cl 0.4871(5) 0.1736(8) 0.0955(7) 0.080(3) Uani 0.30 1 d P A 1
Cl3 Cl 0.49480(19) 0.1055(3) 0.0976(2) 0.0586(8) Uani 0.70 1 d P A 2
C24 C 0.5179(3) 0.1427(4) 0.2314(3) 0.0306(10) Uani 1 1 d . . .
H24 H 0.5750 0.1000 0.2427 0.037 Uiso 1 1 calc R A 1
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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 O1 C3 91.1(2) . .
O3 N1 C7 119.7(3) . .
O3 N1 C11 120.2(3) . .
C7 N1 C11 120.0(3) . .
C2 C1 C6 117.8(3) . .
C2 C1 C3 84.2(3) . .
C6 C1 C3 106.0(3) . .
C2 C1 H1 114.9 . .
C6 C1 H1 114.9 . .
C3 C1 H1 114.9 . .
O2 C2 O1 125.5(3) . .
O2 C2 C1 139.4(4) . .
O1 C2 C1 95.1(3) . .
O1 C3 C7 109.1(3) . .
O1 C3 C4 110.8(3) . .
C7 C3 C4 117.5(3) . .
O1 C3 C1 89.6(2) . .
C7 C3 C1 118.3(3) . .
C4 C3 C1 108.1(3) . .
C3 C4 C5 104.6(3) . .
C3 C4 H4A 110.8 . .
C5 C4 H4A 110.8 . .
C3 C4 H4B 110.8 . .
C5 C4 H4B 110.8 . .
H4A C4 H4B 108.9 . .
C12 C5 C4 115.2(3) . .
C12 C5 C6 111.9(3) . .
C4 C5 C6 104.6(3) . .
C12 C5 H5 108.3 . .
C4 C5 H5 108.3 . .
C6 C5 H5 108.3 . .
C18 C6 C1 115.9(3) . .
C18 C6 C5 115.7(3) . .
C1 C6 C5 104.4(3) . .
C18 C6 H6 106.7 . .
C1 C6 H6 106.7 . .
C5 C6 H6 106.7 . .
N1 C7 C8 119.6(3) . .
N1 C7 C3 115.7(3) . .
C8 C7 C3 124.7(3) . .
C9 C8 C7 120.8(3) . .
C9 C8 H8 119.6 . .
C7 C8 H8 119.6 . .
C10 C9 C8 118.5(3) . .
C10 C9 H9 120.8 . .
C8 C9 H9 120.8 . .
C11 C10 C9 119.8(3) . .
C11 C10 H10 120.1 . .
C9 C10 H10 120.1 . .
N1 C11 C10 121.2(3) . .
N1 C11 H11 119.4 . .
C10 C11 H11 119.4 . .
C13 C12 C17 119.0(4) . .
C13 C12 C5 119.9(3) . .
C17 C12 C5 121.1(3) . .
C12 C13 C14 120.3(4) . .
C12 C13 H13 119.8 . .
C14 C13 H13 119.8 . .
C15 C14 C13 120.0(4) . .
C15 C14 H14 120.0 . .
C13 C14 H14 120.0 . .
C16 C15 C14 120.9(4) . .
C16 C15 H15 119.6 . .
C14 C15 H15 119.6 . .
C15 C16 C17 120.0(4) . .
C15 C16 H16 120.0 . .
C17 C16 H16 120.0 . .
C12 C17 C16 119.8(4) . .
C12 C17 H17 120.1 . .
C16 C17 H17 120.1 . .
C23 C18 C19 118.7(3) . .
C23 C18 C6 121.7(3) . .
C19 C18 C6 119.5(3) . .
C18 C19 C20 120.1(4) . .
C18 C19 H19 120.0 . .
C20 C19 H19 120.0 . .
C21 C20 C19 119.9(4) . .
C21 C20 H20 120.0 . .
C19 C20 H20 120.0 . .
C20 C21 C22 120.8(4) . .
C20 C21 H21 119.6 . .
C22 C21 H21 119.6 . .
C21 C22 C23 119.5(4) . .
C21 C22 H22 120.2 . .
C23 C22 H22 120.2 . .
C18 C23 C22 120.9(4) . .
C18 C23 H23 119.5 . .
C22 C23 H23 119.5 . .
Cl2 C24 Cl1 111.1(2) . .
Cl2 C24 Cl3 115.6(3) . .
Cl1 C24 Cl3 107.9(2) . .
Cl2 C24 Cl3' 90.5(4) . .
Cl1 C24 Cl3' 116.0(4) . .
Cl3 C24 Cl3' 25.5(3) . .
Cl2 C24 H24 112.5 . .
Cl1 C24 H24 112.5 . .
Cl3 C24 H24 96.6 . .
Cl3' C24 H24 112.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.386(4) .
O1 C3 1.493(4) .
O2 C2 1.189(4) .
O3 N1 1.308(4) .
N1 C7 1.361(4) .
N1 C11 1.362(5) .
C1 C2 1.517(5) .
C1 C6 1.538(5) .
C1 C3 1.549(5) .
C1 H1 1.0000 .
C3 C7 1.495(5) .
C3 C4 1.525(5) .
C4 C5 1.545(5) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C12 1.515(5) .
C5 C6 1.548(5) .
C5 H5 1.0000 .
C6 C18 1.515(5) .
C6 H6 1.0000 .
C7 C8 1.386(5) .
C8 C9 1.386(5) .
C8 H8 0.9500 .
C9 C10 1.383(6) .
C9 H9 0.9500 .
C10 C11 1.374(5) .
C10 H10 0.9500 .
C11 H11 0.9500 .
C12 C13 1.392(5) .
C12 C17 1.394(5) .
C13 C14 1.396(6) .
C13 H13 0.9500 .
C14 C15 1.369(7) .
C14 H14 0.9500 .
C15 C16 1.367(7) .
C15 H15 0.9500 .
C16 C17 1.408(6) .
C16 H16 0.9500 .
C17 H17 0.9500 .
C18 C23 1.389(5) .
C18 C19 1.389(5) .
C19 C20 1.408(6) .
C19 H19 0.9500 .
C20 C21 1.370(6) .
C20 H20 0.9500 .
C21 C22 1.373(6) .
C21 H21 0.9500 .
C22 C23 1.396(5) .
C22 H22 0.9500 .
C23 H23 0.9500 .
Cl1 C24 1.750(4) .
Cl2 C24 1.744(5) .
Cl3' C24 1.794(9) .
Cl3 C24 1.768(5) .
C24 H24 1.0000 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C3 O1 C2 O2 177.0(4) . . . .
C3 O1 C2 C1 -2.0(3) . . . .
C6 C1 C2 O2 78.1(6) . . . .
C3 C1 C2 O2 -176.9(5) . . . .
C6 C1 C2 O1 -103.1(3) . . . .
C3 C1 C2 O1 1.9(3) . . . .
C2 O1 C3 C7 -118.0(3) . . . .
C2 O1 C3 C4 111.1(3) . . . .
C2 O1 C3 C1 1.9(3) . . . .
C2 C1 C3 O1 -1.7(2) . . . .
C6 C1 C3 O1 115.6(3) . . . .
C2 C1 C3 C7 109.8(3) . . . .
C6 C1 C3 C7 -132.9(3) . . . .
C2 C1 C3 C4 -113.6(3) . . . .
C6 C1 C3 C4 3.8(4) . . . .
O1 C3 C4 C5 -78.9(3) . . . .
C7 C3 C4 C5 154.8(3) . . . .
C1 C3 C4 C5 17.8(4) . . . .
C3 C4 C5 C12 -155.7(3) . . . .
C3 C4 C5 C6 -32.5(3) . . . .
C2 C1 C6 C18 -60.4(4) . . . .
C3 C1 C6 C18 -152.2(3) . . . .
C2 C1 C6 C5 68.1(4) . . . .
C3 C1 C6 C5 -23.7(3) . . . .
C12 C5 C6 C18 -71.1(4) . . . .
C4 C5 C6 C18 163.5(3) . . . .
C12 C5 C6 C1 160.3(3) . . . .
C4 C5 C6 C1 34.9(3) . . . .
O3 N1 C7 C8 178.0(3) . . . .
C11 N1 C7 C8 -0.5(5) . . . .
O3 N1 C7 C3 -1.1(4) . . . .
C11 N1 C7 C3 -179.6(3) . . . .
O1 C3 C7 N1 166.5(3) . . . .
C4 C3 C7 N1 -66.4(4) . . . .
C1 C3 C7 N1 66.3(4) . . . .
O1 C3 C7 C8 -12.6(5) . . . .
C4 C3 C7 C8 114.5(4) . . . .
C1 C3 C7 C8 -112.8(4) . . . .
N1 C7 C8 C9 1.1(5) . . . .
C3 C7 C8 C9 -179.8(3) . . . .
C7 C8 C9 C10 -1.3(5) . . . .
C8 C9 C10 C11 0.8(5) . . . .
O3 N1 C11 C10 -178.5(3) . . . .
C7 N1 C11 C10 0.0(5) . . . .
C9 C10 C11 N1 -0.2(5) . . . .
C4 C5 C12 C13 53.9(4) . . . .
C6 C5 C12 C13 -65.4(4) . . . .
C4 C5 C12 C17 -128.0(4) . . . .
C6 C5 C12 C17 112.7(4) . . . .
C17 C12 C13 C14 -1.3(5) . . . .
C5 C12 C13 C14 176.8(3) . . . .
C12 C13 C14 C15 0.9(6) . . . .
C13 C14 C15 C16 0.4(6) . . . .
C14 C15 C16 C17 -1.2(6) . . . .
C13 C12 C17 C16 0.5(5) . . . .
C5 C12 C17 C16 -177.6(3) . . . .
C15 C16 C17 C12 0.7(6) . . . .
C1 C6 C18 C23 74.4(4) . . . .
C5 C6 C18 C23 -48.4(5) . . . .
C1 C6 C18 C19 -104.8(4) . . . .
C5 C6 C18 C19 132.5(3) . . . .
C23 C18 C19 C20 -0.1(5) . . . .
C6 C18 C19 C20 179.0(3) . . . .
C18 C19 C20 C21 -0.5(6) . . . .
C19 C20 C21 C22 0.4(6) . . . .
C20 C21 C22 C23 0.4(6) . . . .
C19 C18 C23 C22 0.9(5) . . . .
C6 C18 C23 C22 -178.2(3) . . . .
C21 C22 C23 C18 -1.1(5) . . . .
