#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:02:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178417 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/38/4023813.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_4023813
loop_
_publ_author_name
'Abu T. Khan'
'Tasneem Parvin'
'Lokman H. Choudhury'
_publ_section_title
;
 Effects of Substituents in the β-Position of 1,3-Dicarbonyl Compounds
 in Bromodimethylsulfonium Bromide-Catalyzed Multicomponent
 Reactions: A Facile Access to Functionalized Piperidines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8398
_journal_page_last               8402
_journal_paper_doi               10.1021/jo8014962
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C31 H26 Cl2 N2 O2'
_chemical_formula_weight         529.44
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_cell_angle_alpha                103.1880(10)
_cell_angle_beta                 105.7350(10)
_cell_angle_gamma                98.5930(10)
_cell_formula_units_Z            2
_cell_length_a                   10.1383(3)
_cell_length_b                   10.6645(3)
_cell_length_c                   13.7231(4)
_cell_measurement_reflns_used    5258
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.36
_cell_measurement_theta_min      2.59
_cell_volume                     1354.67(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0170
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16678
_diffrn_reflns_theta_full        28.37
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         6665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0638P)²+0.2663P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1395
_reflns_number_gt                4835
_reflns_number_total             6665
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8014962_si_001.cif
_cod_data_source_block           tppip4cl_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023813
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.14605(7) 0.99763(7) 0.45655(5) 0.0920(2) Uani 1 1 d . . .
Cl2 Cl 0.41216(8) -0.16963(5) 0.09168(6) 0.0904(2) Uani 1 1 d . . .
C7 C 0.57892(15) 0.53204(14) 0.33542(11) 0.0401(3) Uani 1 1 d . . .
C13 C 0.29068(15) 0.65394(15) 0.28969(12) 0.0405(3) Uani 1 1 d . . .
C25 C 0.39504(16) 0.23752(15) 0.26946(12) 0.0428(3) Uani 1 1 d . . .
C12 C 0.64079(17) 0.64921(16) 0.31929(13) 0.0475(4) Uani 1 1 d . . .
H12 H 0.5839 0.6961 0.2838 0.057 Uiso 1 1 calc R . .
C16 C 0.19955(19) 0.86328(18) 0.39287(16) 0.0564(4) Uani 1 1 d . . .
C8 C 0.66952(17) 0.46678(16) 0.39153(13) 0.0478(4) Uani 1 1 d . . .
H8 H 0.6321 0.3896 0.4046 0.057 Uiso 1 1 calc R . .
C14 C 0.35795(19) 0.71878(18) 0.39598(13) 0.0513(4) Uani 1 1 d . . .
H14 H 0.4344 0.6915 0.4330 0.062 Uiso 1 1 calc R . .
C18 C 0.17657(17) 0.69737(16) 0.23704(14) 0.0495(4) Uani 1 1 d . . .
H18 H 0.1299 0.6555 0.1658 0.059 Uiso 1 1 calc R . .
C19 C -0.05376(17) 0.16783(17) 0.17208(14) 0.0506(4) Uani 1 1 d . . .
C26 C 0.4155(2) 0.21610(18) 0.17164(14) 0.0547(4) Uani 1 1 d . . .
H26 H 0.4260 0.2863 0.1427 0.066 Uiso 1 1 calc R . .
C29 C 0.3961(2) 0.00830(17) 0.25985(16) 0.0603(5) Uani 1 1 d . . .
H29 H 0.3933 -0.0606 0.2908 0.072 Uiso 1 1 calc R . .
C15 C 0.3131(2) 0.8236(2) 0.44790(14) 0.0589(4) Uani 1 1 d . . .
H15 H 0.3592 0.8664 0.5190 0.071 Uiso 1 1 calc R . .
C30 C 0.38702(19) 0.13195(17) 0.31283(14) 0.0520(4) Uani 1 1 d . . .
H30 H 0.3752 0.1448 0.3790 0.062 Uiso 1 1 calc R . .
C11 C 0.78529(19) 0.69587(18) 0.35559(15) 0.0562(4) Uani 1 1 d . . .
H11 H 0.8241 0.7731 0.3432 0.067 Uiso 1 1 calc R . .
C17 C 0.13097(19) 0.80120(18) 0.28804(16) 0.0581(4) Uani 1 1 d . . .
H17 H 0.0544 0.8288 0.2516 0.070 Uiso 1 1 calc R . .
C28 C 0.4094(2) -0.01123(17) 0.16111(16) 0.0583(4) Uani 1 1 d . . .
C9 C 0.81352(18) 0.51561(19) 0.42755(15) 0.0575(4) Uani 1 1 d . . .
H9 H 0.8714 0.4706 0.4644 0.069 Uiso 1 1 calc R . .
C10 C 0.87284(19) 0.6298(2) 0.40981(16) 0.0625(5) Uani 1 1 d . . .
H10 H 0.9699 0.6618 0.4339 0.075 Uiso 1 1 calc R . .
C27 C 0.4207(2) 0.09205(19) 0.11653(15) 0.0615(5) Uani 1 1 d . . .
H27 H 0.4316 0.0782 0.0500 0.074 Uiso 1 1 calc R . .
C20 C -0.0916(2) 0.03293(19) 0.12827(17) 0.0666(5) Uani 1 1 d . . .
H20 H -0.0582 -0.0061 0.0748 0.080 Uiso 1 1 calc R . .
C21 C -0.1797(2) -0.0447(2) 0.1639(2) 0.0770(6) Uani 1 1 d . . .
H21 H -0.2065 -0.1357 0.1332 0.092 Uiso 1 1 calc R . .
C24 C -0.1048(2) 0.2245(2) 0.25108(18) 0.0695(5) Uani 1 1 d . . .
H24 H -0.0817 0.3157 0.2800 0.083 Uiso 1 1 calc R . .
C22 C -0.2272(2) 0.0111(2) 0.2435(2) 0.0756(6) Uani 1 1 d . . .
H22 H -0.2845 -0.0418 0.2681 0.091 Uiso 1 1 calc R . .
C23 C -0.1902(2) 0.1453(3) 0.2871(2) 0.0832(7) Uani 1 1 d . . .
H23 H -0.2228 0.1835 0.3413 0.100 Uiso 1 1 calc R . .
N1 N 0.43404(13) 0.48278(12) 0.29952(10) 0.0433(3) Uani 1 1 d . . .
C1 C 0.33886(16) 0.53973(15) 0.22906(11) 0.0398(3) Uani 1 1 d . . .
H1 H 0.3918 0.5759 0.1878 0.048 Uiso 1 1 calc R . .
C5 C 0.37289(16) 0.36883(15) 0.32740(12) 0.0426(3) Uani 1 1 d . . .
H5 H 0.4169 0.3830 0.4032 0.051 Uiso 1 1 calc R . .
C2 C 0.21529(16) 0.43212(15) 0.15152(12) 0.0425(3) Uani 1 1 d . . .
C3 C 0.14644(16) 0.34727(16) 0.19188(12) 0.0442(3) Uani 1 1 d . . .
C4 C 0.21374(16) 0.36025(17) 0.30692(13) 0.0475(4) Uani 1 1 d . . .
H4A H 0.1721 0.2843 0.3249 0.057 Uiso 1 1 calc R . .
H4B H 0.1989 0.4392 0.3501 0.057 Uiso 1 1 calc R . .
N2 N 0.03367(16) 0.24736(15) 0.13371(13) 0.0546(4) Uani 1 1 d . . .
O2 O 0.07655(15) 0.33377(13) -0.02717(10) 0.0671(4) Uani 1 1 d . . .
O1 O 0.25385(15) 0.50931(13) 0.01365(9) 0.0640(4) Uani 1 1 d . . .
C6 C 0.17391(18) 0.41865(16) 0.03987(13) 0.0486(4) Uani 1 1 d . . .
C31 C 0.2168(3) 0.5032(3) -0.09693(16) 0.0949(9) Uani 1 1 d . . .
H31A H 0.2227 0.4187 -0.1366 0.142 Uiso 1 1 calc R . .
H31B H 0.2805 0.5719 -0.1066 0.142 Uiso 1 1 calc R . .
H31C H 0.1224 0.5147 -0.1211 0.142 Uiso 1 1 calc R . .
H2N H 0.008(2) 0.237(2) 0.0697(17) 0.062(6) Uiso 1 1 d . . .
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
_geom_angle_publ_flag
N1 C7 C8 120.79(13) . . ?
N1 C7 C12 122.02(13) . . ?
C8 C7 C12 117.18(14) . . ?
C18 C13 C14 117.74(15) . . ?
C18 C13 C1 119.52(13) . . ?
C14 C13 C1 122.73(13) . . ?
C30 C25 C26 117.94(15) . . ?
C30 C25 C5 119.30(14) . . ?
C26 C25 C5 122.66(14) . . ?
C11 C12 C7 120.86(15) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C17 C16 C15 120.96(16) . . ?
C17 C16 Cl1 119.61(15) . . ?
C15 C16 Cl1 119.40(15) . . ?
C9 C8 C7 120.95(15) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C15 C14 C13 121.18(16) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C17 C18 C13 121.50(16) . . ?
C17 C18 H18 119.2 . . ?
C13 C18 H18 119.2 . . ?
C20 C19 C24 119.35(18) . . ?
C20 C19 N2 119.84(17) . . ?
C24 C19 N2 120.79(16) . . ?
C27 C26 C25 121.03(16) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C28 C29 C30 119.06(16) . . ?
C28 C29 H29 120.5 . . ?
C30 C29 H29 120.5 . . ?
C16 C15 C14 119.21(17) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C29 C30 C25 121.53(16) . . ?
C29 C30 H30 119.2 . . ?
C25 C30 H30 119.2 . . ?
C12 C11 C10 121.18(17) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C16 C17 C18 119.42(16) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C29 C28 C27 120.92(17) . . ?
C29 C28 Cl2 118.94(14) . . ?
C27 C28 Cl2 120.13(15) . . ?
C8 C9 C10 121.19(16) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 118.64(16) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C26 C27 C28 119.39(17) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C19 C20 C21 120.0(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 120.6(2) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C19 C24 C23 119.9(2) . . ?
C19 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C21 C22 C23 119.7(2) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C22 C23 C24 120.5(2) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C7 N1 C5 120.34(12) . . ?
C7 N1 C1 121.48(12) . . ?
C5 N1 C1 118.13(12) . . ?
N1 C1 C2 110.29(12) . . ?
N1 C1 C13 112.64(12) . . ?
C2 C1 C13 111.97(12) . . ?
N1 C1 H1 107.2 . . ?
C2 C1 H1 107.2 . . ?
C13 C1 H1 107.2 . . ?
N1 C5 C25 114.29(13) . . ?
N1 C5 C4 109.52(12) . . ?
C25 C5 C4 109.39(13) . . ?
N1 C5 H5 107.8 . . ?
C25 C5 H5 107.8 . . ?
C4 C5 H5 107.8 . . ?
C3 C2 C6 121.33(14) . . ?
C3 C2 C1 117.16(13) . . ?
C6 C2 C1 121.50(14) . . ?
N2 C3 C2 124.44(15) . . ?
N2 C3 C4 119.70(15) . . ?
C2 C3 C4 115.51(14) . . ?
C3 C4 C5 108.29(13) . . ?
C3 C4 H4A 110.0 . . ?
C5 C4 H4A 110.0 . . ?
C3 C4 H4B 110.0 . . ?
C5 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
C3 N2 C19 126.98(16) . . ?
C3 N2 H2N 116.3(14) . . ?
C19 N2 H2N 116.4(14) . . ?
C6 O1 C31 116.52(15) . . ?
O2 C6 O1 121.41(15) . . ?
O2 C6 C2 125.07(16) . . ?
O1 C6 C2 113.51(14) . . ?
O1 C31 H31A 109.5 . . ?
O1 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O1 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C16 1.7403(18) . ?
Cl2 C28 1.7483(19) . ?
C7 N1 1.3911(19) . ?
C7 C8 1.405(2) . ?
C7 C12 1.404(2) . ?
C13 C18 1.391(2) . ?
C13 C14 1.389(2) . ?
C13 C1 1.533(2) . ?
C25 C30 1.390(2) . ?
C25 C26 1.387(2) . ?
C25 C5 1.525(2) . ?
C12 C11 1.384(2) . ?
C12 H12 0.9300 . ?
C16 C17 1.370(3) . ?
C16 C15 1.377(3) . ?
C8 C9 1.382(2) . ?
C8 H8 0.9300 . ?
C14 C15 1.388(2) . ?
C14 H14 0.9300 . ?
C18 C17 1.380(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.376(3) . ?
C19 C24 1.381(3) . ?
C19 N2 1.419(2) . ?
C26 C27 1.382(3) . ?
C26 H26 0.9300 . ?
C29 C28 1.370(3) . ?
C29 C30 1.383(3) . ?
C29 H29 0.9300 . ?
C15 H15 0.9300 . ?
C30 H30 0.9300 . ?
C11 C10 1.380(3) . ?
C11 H11 0.9300 . ?
C17 H17 0.9300 . ?
C28 C27 1.381(3) . ?
C9 C10 1.379(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C27 H27 0.9300 . ?
C20 C21 1.386(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.362(3) . ?
C21 H21 0.9300 . ?
C24 C23 1.383(3) . ?
C24 H24 0.9300 . ?
C22 C23 1.369(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
N1 C5 1.4571(19) . ?
N1 C1 1.4738(18) . ?
C1 C2 1.520(2) . ?
C1 H1 0.9800 . ?
C5 C4 1.546(2) . ?
C5 H5 0.9800 . ?
C2 C3 1.365(2) . ?
C2 C6 1.441(2) . ?
C3 N2 1.354(2) . ?
C3 C4 1.505(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
N2 H2N 0.82(2) . ?
O2 C6 1.225(2) . ?
O1 C6 1.343(2) . ?
O1 C31 1.444(2) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
