#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/38/4023814.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_4023814
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            'C32 H30 N2 O2'
_chemical_formula_weight         474.58
_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                106.190(3)
_cell_angle_beta                 108.639(3)
_cell_angle_gamma                99.894(2)
_cell_formula_units_Z            2
_cell_length_a                   9.7957(3)
_cell_length_b                   11.0139(4)
_cell_length_c                   13.9330(6)
_cell_measurement_reflns_used    3877
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.17
_cell_measurement_theta_min      2.58
_cell_volume                     1310.44(8)
_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 0.957
_diffrn_measured_fraction_theta_max 0.907
_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  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15836
_diffrn_reflns_theta_full        28.39
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5946
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0497
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1438
_refine_ls_wR_factor_ref         0.1701
_reflns_number_gt                3550
_reflns_number_total             5946
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8014962_si_002.cif
_cod_data_source_block           tp-pip-eaa
_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               4023814
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
O2 O 0.05903(15) 0.85766(12) 1.01989(8) 0.0676(4) Uani 1 1 d . . .
O1 O 0.21506(14) 0.97104(12) 0.96616(8) 0.0642(4) Uani 1 1 d . . .
N1 N 0.11358(15) 0.68894(13) 0.68902(10) 0.0507(4) Uani 1 1 d . . .
C2 C 0.03014(18) 0.78116(17) 0.83547(11) 0.0480(4) Uani 1 1 d . . .
C1 C 0.08199(18) 0.80672(16) 0.74945(11) 0.0489(4) Uani 1 1 d . . .
H1 H 0.1776 0.8768 0.7877 0.059 Uiso 1 1 calc R . .
C7 C 0.23071(18) 0.70082(17) 0.65286(11) 0.0492(4) Uani 1 1 d . . .
C5 C 0.02539(18) 0.55917(16) 0.67372(11) 0.0499(4) Uani 1 1 d . . .
H5 H -0.0030 0.5020 0.5984 0.060 Uiso 1 1 calc R . .
C6 C 0.09844(19) 0.87038(17) 0.94681(12) 0.0515(4) Uani 1 1 d . . .
C3 C -0.07604(18) 0.66418(17) 0.80493(11) 0.0486(4) Uani 1 1 d . . .
C25 C 0.10820(19) 0.49328(17) 0.74698(12) 0.0515(4) Uani 1 1 d . . .
C19 C -0.2399(2) 0.49997(18) 0.83991(12) 0.0522(4) Uani 1 1 d . . .
C13 C -0.02670(18) 0.85762(16) 0.67498(12) 0.0500(4) Uani 1 1 d . . .
C8 C 0.27651(19) 0.59111(18) 0.61196(12) 0.0554(4) Uani 1 1 d . . .
H8 H 0.2267 0.5085 0.6073 0.066 Uiso 1 1 calc R . .
C4 C -0.12018(18) 0.57172(18) 0.69088(11) 0.0531(4) Uani 1 1 d . . .
H4A H -0.1780 0.6061 0.6396 0.064 Uiso 1 1 calc R . .
H4B H -0.1814 0.4860 0.6799 0.064 Uiso 1 1 calc R . .
C12 C 0.3064(2) 0.8220(2) 0.65464(14) 0.0623(5) Uani 1 1 d . . .
H12 H 0.2765 0.8966 0.6787 0.075 Uiso 1 1 calc R . .
C26 C 0.2300(2) 0.56477(19) 0.84381(13) 0.0602(5) Uani 1 1 d . . .
H26 H 0.2667 0.6554 0.8628 0.072 Uiso 1 1 calc R . .
C14 C -0.0633(2) 0.8155(2) 0.56385(13) 0.0653(5) Uani 1 1 d . . .
H14 H -0.0245 0.7511 0.5324 0.078 Uiso 1 1 calc R . .
C18 C -0.0892(2) 0.95223(18) 0.71813(14) 0.0632(5) Uani 1 1 d . . .
H18 H -0.0670 0.9823 0.7923 0.076 Uiso 1 1 calc R . .
C11 C 0.4253(2) 0.8322(2) 0.62102(16) 0.0733(6) Uani 1 1 d . . .
H11 H 0.4750 0.9140 0.6242 0.088 Uiso 1 1 calc R . .
C30 C 0.0575(2) 0.3581(2) 0.71987(18) 0.0727(6) Uani 1 1 d . . .
H30 H -0.0235 0.3074 0.6551 0.087 Uiso 1 1 calc R . .
C10 C 0.4712(2) 0.7241(2) 0.58316(16) 0.0761(6) Uani 1 1 d . . .
H10 H 0.5516 0.7320 0.5614 0.091 Uiso 1 1 calc R . .
C9 C 0.3954(2) 0.6038(2) 0.57822(14) 0.0681(5) Uani 1 1 d . . .
H9 H 0.4243 0.5294 0.5518 0.082 Uiso 1 1 calc R . .
C24 C -0.1947(3) 0.3982(2) 0.86585(15) 0.0721(6) Uani 1 1 d . . .
H24 H -0.0936 0.4084 0.9035 0.086 Uiso 1 1 calc R . .
C20 C -0.3896(2) 0.4835(2) 0.78500(16) 0.0740(6) Uani 1 1 d . . .
H20 H -0.4203 0.5531 0.7685 0.089 Uiso 1 1 calc R . .
C15 C -0.1566(2) 0.8674(2) 0.49884(16) 0.0809(6) Uani 1 1 d . . .
H15 H -0.1782 0.8392 0.4248 0.097 Uiso 1 1 calc R . .
C17 C -0.1831(3) 1.0023(2) 0.65337(19) 0.0806(6) Uani 1 1 d . . .
H17 H -0.2242 1.0652 0.6840 0.097 Uiso 1 1 calc R . .
C16 C -0.2167(2) 0.9603(2) 0.54385(18) 0.0830(6) Uani 1 1 d . . .
H16 H -0.2801 0.9948 0.5004 0.100 Uiso 1 1 calc R . .
C27 C 0.2981(3) 0.5045(3) 0.91256(16) 0.0811(6) Uani 1 1 d . . .
H27 H 0.3794 0.5547 0.9773 0.097 Uiso 1 1 calc R . .
C29 C 0.1281(3) 0.2981(3) 0.7900(3) 0.0950(8) Uani 1 1 d . . .
H29 H 0.0940 0.2072 0.7712 0.114 Uiso 1 1 calc R . .
C23 C -0.3031(4) 0.2787(2) 0.83470(19) 0.0937(8) Uani 1 1 d . . .
H23 H -0.2742 0.2088 0.8520 0.112 Uiso 1 1 calc R . .
C28 C 0.2464(3) 0.3714(3) 0.8857(2) 0.0946(8) Uani 1 1 d . . .
H28 H 0.2916 0.3308 0.9325 0.113 Uiso 1 1 calc R . .
C22 C -0.4513(4) 0.2641(3) 0.7789(2) 0.0960(8) Uani 1 1 d . . .
H22 H -0.5229 0.1842 0.7578 0.115 Uiso 1 1 calc R . .
C21 C -0.4941(3) 0.3657(3) 0.7544(2) 0.0976(8) Uani 1 1 d . . .
H21 H -0.5951 0.3554 0.7164 0.117 Uiso 1 1 calc R . .
N2 N -0.13208(17) 0.62379(16) 0.87126(11) 0.0591(4) Uani 1 1 d . . .
C31 C 0.2921(2) 1.0649(2) 1.07679(14) 0.0739(6) Uani 1 1 d . . .
H31A H 0.3236 1.0190 1.1264 0.089 Uiso 1 1 calc R . .
H31B H 0.2254 1.1127 1.0975 0.089 Uiso 1 1 calc R . .
C32 C 0.4239(3) 1.1570(2) 1.08141(18) 0.0927(7) Uani 1 1 d . . .
H32A H 0.4940 1.1103 1.0682 0.139 Uiso 1 1 calc R . .
H32B H 0.4711 1.2253 1.1519 0.139 Uiso 1 1 calc R . .
H32C H 0.3926 1.1957 1.0272 0.139 Uiso 1 1 calc R . .
H1N H -0.090(2) 0.6831(19) 0.9394(16) 0.081(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'
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
C6 O1 C31 117.27(13) . . ?
C7 N1 C5 120.27(12) . . ?
C7 N1 C1 121.16(13) . . ?
C5 N1 C1 118.46(11) . . ?
C3 C2 C6 121.03(14) . . ?
C3 C2 C1 117.06(13) . . ?
C6 C2 C1 121.70(15) . . ?
N1 C1 C2 110.56(13) . . ?
N1 C1 C13 112.82(12) . . ?
C2 C1 C13 112.58(12) . . ?
N1 C1 H1 106.8 . . ?
C2 C1 H1 106.8 . . ?
C13 C1 H1 106.8 . . ?
N1 C7 C8 121.04(16) . . ?
N1 C7 C12 121.84(15) . . ?
C8 C7 C12 117.12(15) . . ?
N1 C5 C25 114.28(13) . . ?
N1 C5 C4 108.85(13) . . ?
C25 C5 C4 109.89(12) . . ?
N1 C5 H5 107.9 . . ?
C25 C5 H5 107.9 . . ?
C4 C5 H5 107.9 . . ?
O2 C6 O1 121.42(14) . . ?
O2 C6 C2 125.04(17) . . ?
O1 C6 C2 113.53(13) . . ?
N2 C3 C2 125.06(14) . . ?
N2 C3 C4 119.32(15) . . ?
C2 C3 C4 115.39(13) . . ?
C30 C25 C26 118.01(17) . . ?
C30 C25 C5 119.73(16) . . ?
C26 C25 C5 122.19(16) . . ?
C24 C19 C20 119.80(19) . . ?
C24 C19 N2 120.29(17) . . ?
C20 C19 N2 119.90(17) . . ?
C18 C13 C14 117.34(16) . . ?
C18 C13 C1 120.23(13) . . ?
C14 C13 C1 122.40(14) . . ?
C9 C8 C7 120.91(18) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C3 C4 C5 107.74(13) . . ?
C3 C4 H4A 110.2 . . ?
C5 C4 H4A 110.2 . . ?
C3 C4 H4B 110.2 . . ?
C5 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
C11 C12 C7 120.81(17) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C27 C26 C25 121.5(2) . . ?
C27 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?
C15 C14 C13 121.36(17) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C17 C18 C13 121.22(17) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
C10 C11 C12 121.43(19) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C25 C30 C29 119.9(2) . . ?
C25 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C11 C10 C9 118.41(17) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C10 C9 C8 121.28(18) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C19 C24 C23 118.9(2) . . ?
C19 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
C21 C20 C19 120.6(2) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C16 C15 C14 119.86(18) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C16 C17 C18 120.54(19) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C15 C16 C17 119.67(19) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C28 C27 C26 120.1(2) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C28 C29 C30 120.8(2) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C22 C23 C24 120.3(2) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C27 C28 C29 119.6(2) . . ?
C27 C28 H28 120.2 . . ?
C29 C28 H28 120.2 . . ?
C21 C22 C23 120.1(2) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C21 C20 120.3(2) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C3 N2 C19 124.95(14) . . ?
C3 N2 H1N 111.7(13) . . ?
C19 N2 H1N 123.3(13) . . ?
O1 C31 C32 107.89(16) . . ?
O1 C31 H31A 110.1 . . ?
C32 C31 H31A 110.1 . . ?
O1 C31 H31B 110.1 . . ?
C32 C31 H31B 110.1 . . ?
H31A C31 H31B 108.4 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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
O2 C6 1.2319(18) . ?
O1 C6 1.345(2) . ?
O1 C31 1.454(2) . ?
N1 C7 1.3935(19) . ?
N1 C5 1.457(2) . ?
N1 C1 1.4775(19) . ?
C2 C3 1.369(2) . ?
C2 C6 1.442(2) . ?
C2 C1 1.517(2) . ?
C1 C13 1.532(2) . ?
C1 H1 0.9800 . ?
C7 C8 1.397(2) . ?
C7 C12 1.401(2) . ?
C5 C25 1.521(2) . ?
C5 C4 1.542(2) . ?
C5 H5 0.9800 . ?
C3 N2 1.350(2) . ?
C3 C4 1.502(2) . ?
C25 C30 1.385(2) . ?
C25 C26 1.386(2) . ?
C19 C24 1.370(3) . ?
C19 C20 1.372(3) . ?
C19 N2 1.430(2) . ?
C13 C18 1.388(2) . ?
C13 C14 1.389(2) . ?
C8 C9 1.388(2) . ?
C8 H8 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C12 C11 1.386(2) . ?
C12 H12 0.9300 . ?
C26 C27 1.379(3) . ?
C26 H26 0.9300 . ?
C14 C15 1.386(3) . ?
C14 H14 0.9300 . ?
C18 C17 1.373(3) . ?
C18 H18 0.9300 . ?
C11 C10 1.373(3) . ?
C11 H11 0.9300 . ?
C30 C29 1.398(3) . ?
C30 H30 0.9300 . ?
C10 C9 1.375(3) . ?
C10 H10 0.9300 . ?
C9 H9 0.9300 . ?
C24 C23 1.398(3) . ?
C24 H24 0.9300 . ?
C20 C21 1.367(3) . ?
C20 H20 0.9300 . ?
C15 C16 1.369(3) . ?
C15 H15 0.9300 . ?
C17 C16 1.372(3) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C27 C28 1.366(3) . ?
C27 H27 0.9300 . ?
C29 C28 1.366(4) . ?
C29 H29 0.9300 . ?
C23 C22 1.366(4) . ?
C23 H23 0.9300 . ?
C28 H28 0.9300 . ?
C22 C21 1.352(4) . ?
C22 H22 0.9300 . ?
C21 H21 0.9300 . ?
N2 H1N 0.90(2) . ?
C31 C32 1.469(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 23335092
