#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/73/7117327.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_7117327
loop_
_publ_author_name
'Min Tang'
'Dong Xing'
'Haoxi Huang'
'Wenhao Hu'
_publ_section_title
;
 Divergent synthesis of chiral heterocycles via sequencing of
 enantioselective three-component reactions and one-pot subsequent
 cyclization reactions
;
_journal_name_full               Chem.Commun.
_journal_page_first              10612
_journal_paper_doi               10.1039/C5cc01979F
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C24 H23 N O4'
_chemical_formula_weight         389.43
_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
_audit_update_record
;
2013-12-07 deposited with the CCDC.
2015-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                96.918(2)
_cell_angle_beta                 104.753(2)
_cell_angle_gamma                99.920(2)
_cell_formula_units_Z            2
_cell_length_a                   9.9379(6)
_cell_length_b                   10.0008(6)
_cell_length_c                   10.8276(6)
_cell_measurement_temperature    296(2)
_cell_volume                     1009.72(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11829
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9811
_exptl_absorpt_correction_T_min  0.9643
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3528
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0450
_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)+(0.0507P)²+0.1786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1226
_reflns_number_gt                2240
_reflns_number_total             3528
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc01979f21_2.cif
_cod_data_source_block           z
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7117327
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
O1 O -0.02977(14) 0.22674(15) 0.87052(17) 0.0572(5) Uani 1 1 d . . .
O2 O 0.14243(15) 0.41280(15) 0.90514(16) 0.0566(5) Uani 1 1 d . . .
O3 O 0.62687(15) 0.38055(16) 1.07838(16) 0.0609(5) Uani 1 1 d . . .
H3A H 0.6971 0.4413 1.0866 0.091 Uiso 1 1 calc R . .
O4 O 0.13492(14) 0.06078(13) 0.91782(14) 0.0445(4) Uani 1 1 d . . .
N1 N 0.42035(17) 0.15574(17) 1.07539(17) 0.0407(4) Uani 1 1 d . . .
C1 C 0.2651(2) 0.2959(2) 1.1570(2) 0.0415(5) Uani 1 1 d . . .
C2 C 0.1426(2) 0.2220(2) 1.1763(2) 0.0483(6) Uani 1 1 d . . .
H2A H 0.0912 0.1429 1.1176 0.058 Uiso 1 1 calc R . .
C3 C 0.0960(2) 0.2643(3) 1.2813(2) 0.0579(7) Uani 1 1 d . . .
H3B H 0.0126 0.2148 1.2917 0.069 Uiso 1 1 calc R . .
C4 C 0.1722(3) 0.3789(3) 1.3704(3) 0.0613(7) Uani 1 1 d . . .
H4A H 0.1408 0.4067 1.4414 0.074 Uiso 1 1 calc R . .
C5 C 0.2945(3) 0.4526(3) 1.3547(3) 0.0582(7) Uani 1 1 d . . .
H5A H 0.3469 0.5298 1.4155 0.070 Uiso 1 1 calc R . .
C6 C 0.3402(2) 0.4122(2) 1.2485(2) 0.0511(6) Uani 1 1 d . . .
H6A H 0.4226 0.4636 1.2379 0.061 Uiso 1 1 calc R . .
C7 C 0.2629(2) 0.1903(2) 0.7939(2) 0.0446(6) Uani 1 1 d . . .
C8 C 0.4004(2) 0.2443(2) 0.7934(2) 0.0487(6) Uani 1 1 d . . .
H8A H 0.4687 0.2865 0.8706 0.058 Uiso 1 1 calc R . .
C9 C 0.4364(3) 0.2356(2) 0.6777(3) 0.0587(7) Uani 1 1 d . . .
H9A H 0.5293 0.2716 0.6781 0.070 Uiso 1 1 calc R . .
C10 C 0.3377(3) 0.1748(3) 0.5626(3) 0.0647(7) Uani 1 1 d . . .
H10A H 0.3626 0.1708 0.4853 0.078 Uiso 1 1 calc R . .
C11 C 0.2016(3) 0.1199(3) 0.5631(3) 0.0745(8) Uani 1 1 d . . .
H11A H 0.1339 0.0773 0.4856 0.089 Uiso 1 1 calc R . .
C12 C 0.1646(3) 0.1274(3) 0.6766(3) 0.0629(7) Uani 1 1 d . . .
H12A H 0.0718 0.0897 0.6752 0.075 Uiso 1 1 calc R . .
C13 C 0.5394(2) 0.2077(2) 1.1865(2) 0.0417(5) Uani 1 1 d . . .
C14 C 0.5603(2) 0.1457(2) 1.2965(2) 0.0534(6) Uani 1 1 d . . .
H14A H 0.4923 0.0706 1.2996 0.064 Uiso 1 1 calc R . .
C15 C 0.6801(3) 0.1935(3) 1.4013(3) 0.0637(7) Uani 1 1 d . . .
H15A H 0.6923 0.1497 1.4732 0.076 Uiso 1 1 calc R . .
C16 C 0.7806(3) 0.3048(3) 1.3996(3) 0.0619(7) Uani 1 1 d . . .
H16A H 0.8609 0.3369 1.4701 0.074 Uiso 1 1 calc R . .
C17 C 0.7621(2) 0.3691(3) 1.2926(3) 0.0563(7) Uani 1 1 d . . .
H17A H 0.8295 0.4457 1.2916 0.068 Uiso 1 1 calc R . .
C18 C 0.6446(2) 0.3208(2) 1.1875(2) 0.0453(6) Uani 1 1 d . . .
C19 C 0.2102(2) 0.1946(2) 0.9154(2) 0.0410(5) Uani 1 1 d . . .
C20 C 0.3252(2) 0.2545(2) 1.0458(2) 0.0397(5) Uani 1 1 d . . .
H20A H 0.3835 0.3384 1.0330 0.048 Uiso 1 1 calc R . .
C21 C 0.3400(2) 0.0171(2) 1.0712(2) 0.0469(6) Uani 1 1 d . . .
H21A H 0.2933 0.0183 1.1397 0.056 Uiso 1 1 calc R . .
H21B H 0.4045 -0.0458 1.0849 0.056 Uiso 1 1 calc R . .
C22 C 0.2314(2) -0.0309(2) 0.9426(2) 0.0486(6) Uani 1 1 d . . .
H22A H 0.2791 -0.0366 0.8749 0.058 Uiso 1 1 calc R . .
H22B H 0.1781 -0.1224 0.9405 0.058 Uiso 1 1 calc R . .
C23 C 0.1045(2) 0.2897(2) 0.8977(2) 0.0442(6) Uani 1 1 d . . .
C24 C -0.1324(2) 0.3148(3) 0.8498(3) 0.0890(10) Uani 1 1 d . . .
H24A H -0.2268 0.2598 0.8310 0.133 Uiso 1 1 calc R . .
H24B H -0.1245 0.3606 0.7782 0.133 Uiso 1 1 calc R . .
H24C H -0.1138 0.3821 0.9265 0.133 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 0.0000 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
C23 O1 C24 115.66(18) . .
C18 O3 H3A 109.5 . .
C19 O4 C22 110.32(14) . .
C13 N1 C21 115.63(17) . .
C13 N1 C20 113.46(16) . .
C21 N1 C20 111.94(15) . .
C2 C1 C6 117.6(2) . .
C2 C1 C20 124.18(19) . .
C6 C1 C20 118.15(18) . .
C3 C2 C1 120.9(2) . .
C3 C2 H2A 119.5 . .
C1 C2 H2A 119.5 . .
C4 C3 C2 120.3(2) . .
C4 C3 H3B 119.8 . .
C2 C3 H3B 119.8 . .
C5 C4 C3 119.9(2) . .
C5 C4 H4A 120.1 . .
C3 C4 H4A 120.1 . .
C4 C5 C6 120.0(2) . .
C4 C5 H5A 120.0 . .
C6 C5 H5A 120.0 . .
C5 C6 C1 121.2(2) . .
C5 C6 H6A 119.4 . .
C1 C6 H6A 119.4 . .
C8 C7 C12 118.2(2) . .
C8 C7 C19 124.7(2) . .
C12 C7 C19 117.15(19) . .
C7 C8 C9 119.9(2) . .
C7 C8 H8A 120.1 . .
C9 C8 H8A 120.1 . .
C10 C9 C8 121.2(2) . .
C10 C9 H9A 119.4 . .
C8 C9 H9A 119.4 . .
C9 C10 C11 119.0(3) . .
C9 C10 H10A 120.5 . .
C11 C10 H10A 120.5 . .
C12 C11 C10 120.5(3) . .
C12 C11 H11A 119.8 . .
C10 C11 H11A 119.8 . .
C11 C12 C7 121.3(2) . .
C11 C12 H12A 119.4 . .
C7 C12 H12A 119.4 . .
C14 C13 C18 116.8(2) . .
C14 C13 N1 122.2(2) . .
C18 C13 N1 120.9(2) . .
C15 C14 C13 121.5(2) . .
C15 C14 H14A 119.3 . .
C13 C14 H14A 119.3 . .
C16 C15 C14 120.3(2) . .
C16 C15 H15A 119.9 . .
C14 C15 H15A 119.9 . .
C15 C16 C17 119.6(2) . .
C15 C16 H16A 120.2 . .
C17 C16 H16A 120.2 . .
C18 C17 C16 120.4(2) . .
C18 C17 H17A 119.8 . .
C16 C17 H17A 119.8 . .
O3 C18 C17 121.2(2) . .
O3 C18 C13 117.32(19) . .
C17 C18 C13 121.5(2) . .
O4 C19 C23 108.08(15) . .
O4 C19 C7 109.27(17) . .
C23 C19 C7 105.09(17) . .
O4 C19 C20 111.07(17) . .
C23 C19 C20 107.06(17) . .
C7 C19 C20 115.82(16) . .
N1 C20 C1 112.63(17) . .
N1 C20 C19 108.94(16) . .
C1 C20 C19 113.91(16) . .
N1 C20 H20A 107.0 . .
C1 C20 H20A 107.0 . .
C19 C20 H20A 107.0 . .
N1 C21 C22 109.67(18) . .
N1 C21 H21A 109.7 . .
C22 C21 H21A 109.7 . .
N1 C21 H21B 109.7 . .
C22 C21 H21B 109.7 . .
H21A C21 H21B 108.2 . .
O4 C22 C21 111.43(17) . .
O4 C22 H22A 109.3 . .
C21 C22 H22A 109.3 . .
O4 C22 H22B 109.3 . .
C21 C22 H22B 109.3 . .
H22A C22 H22B 108.0 . .
O2 C23 O1 123.2(2) . .
O2 C23 C19 122.01(18) . .
O1 C23 C19 114.74(18) . .
O1 C24 H24A 109.5 . .
O1 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
O1 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C23 1.315(2) .
O1 C24 1.451(3) .
O2 C23 1.211(2) .
O3 C18 1.373(3) .
O3 H3A 0.8200 .
O4 C19 1.423(2) .
O4 C22 1.437(2) .
N1 C13 1.425(3) .
N1 C21 1.465(2) .
N1 C20 1.489(2) .
C1 C2 1.389(3) .
C1 C6 1.392(3) .
C1 C20 1.519(3) .
C2 C3 1.380(3) .
C2 H2A 0.9300 .
C3 C4 1.371(3) .
C3 H3B 0.9300 .
C4 C5 1.370(3) .
C4 H4A 0.9300 .
C5 C6 1.381(3) .
C5 H5A 0.9300 .
C6 H6A 0.9300 .
C7 C8 1.382(3) .
C7 C12 1.388(3) .
C7 C19 1.534(3) .
C8 C9 1.385(3) .
C8 H8A 0.9300 .
C9 C10 1.368(3) .
C9 H9A 0.9300 .
C10 C11 1.371(4) .
C10 H10A 0.9300 .
C11 C12 1.367(4) .
C11 H11A 0.9300 .
C12 H12A 0.9300 .
C13 C14 1.393(3) .
C13 C18 1.399(3) .
C14 C15 1.386(3) .
C14 H14A 0.9300 .
C15 C16 1.366(3) .
C15 H15A 0.9300 .
C16 C17 1.379(3) .
C16 H16A 0.9300 .
C17 C18 1.374(3) .
C17 H17A 0.9300 .
C19 C23 1.527(3) .
C19 C20 1.549(3) .
C20 H20A 0.9800 .
C21 C22 1.493(3) .
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
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
C6 C1 C2 C3 1.2(3) . . . .
C20 C1 C2 C3 178.6(2) . . . .
C1 C2 C3 C4 -1.5(4) . . . .
C2 C3 C4 C5 0.5(4) . . . .
C3 C4 C5 C6 0.7(4) . . . .
C4 C5 C6 C1 -1.0(4) . . . .
C2 C1 C6 C5 0.1(3) . . . .
C20 C1 C6 C5 -177.5(2) . . . .
C12 C7 C8 C9 0.4(3) . . . .
C19 C7 C8 C9 -179.6(2) . . . .
C7 C8 C9 C10 0.4(4) . . . .
C8 C9 C10 C11 -1.0(4) . . . .
C9 C10 C11 C12 0.8(4) . . . .
C10 C11 C12 C7 0.0(4) . . . .
C8 C7 C12 C11 -0.6(4) . . . .
C19 C7 C12 C11 179.4(2) . . . .
C21 N1 C13 C14 -13.6(3) . . . .
C20 N1 C13 C14 117.7(2) . . . .
C21 N1 C13 C18 163.55(18) . . . .
C20 N1 C13 C18 -65.2(2) . . . .
C18 C13 C14 C15 -0.4(3) . . . .
N1 C13 C14 C15 176.9(2) . . . .
C13 C14 C15 C16 0.8(4) . . . .
C14 C15 C16 C17 -0.1(4) . . . .
C15 C16 C17 C18 -0.9(4) . . . .
C16 C17 C18 O3 -177.7(2) . . . .
C16 C17 C18 C13 1.4(3) . . . .
C14 C13 C18 O3 178.4(2) . . . .
N1 C13 C18 O3 1.1(3) . . . .
C14 C13 C18 C17 -0.7(3) . . . .
N1 C13 C18 C17 -178.0(2) . . . .
C22 O4 C19 C23 -176.34(17) . . . .
C22 O4 C19 C7 69.8(2) . . . .
C22 O4 C19 C20 -59.2(2) . . . .
C8 C7 C19 O4 -131.2(2) . . . .
C12 C7 C19 O4 48.9(3) . . . .
C8 C7 C19 C23 113.1(2) . . . .
C12 C7 C19 C23 -66.9(2) . . . .
C8 C7 C19 C20 -4.8(3) . . . .
C12 C7 C19 C20 175.2(2) . . . .
C13 N1 C20 C1 -59.0(2) . . . .
C21 N1 C20 C1 74.1(2) . . . .
C13 N1 C20 C19 173.57(16) . . . .
C21 N1 C20 C19 -53.3(2) . . . .
C2 C1 C20 N1 -86.1(2) . . . .
C6 C1 C20 N1 91.3(2) . . . .
C2 C1 C20 C19 38.6(3) . . . .
C6 C1 C20 C19 -143.94(19) . . . .
O4 C19 C20 N1 55.1(2) . . . .
C23 C19 C20 N1 172.86(15) . . . .
C7 C19 C20 N1 -70.3(2) . . . .
O4 C19 C20 C1 -71.6(2) . . . .
C23 C19 C20 C1 46.2(2) . . . .
C7 C19 C20 C1 163.00(17) . . . .
C13 N1 C21 C22 -172.53(17) . . . .
C20 N1 C21 C22 55.5(2) . . . .
C19 O4 C22 C21 61.3(2) . . . .
N1 C21 C22 O4 -58.6(2) . . . .
C24 O1 C23 O2 -0.2(3) . . . .
C24 O1 C23 C19 -178.4(2) . . . .
O4 C19 C23 O2 172.5(2) . . . .
C7 C19 C23 O2 -70.9(3) . . . .
C20 C19 C23 O2 52.8(3) . . . .
O4 C19 C23 O1 -9.3(3) . . . .
C7 C19 C23 O1 107.3(2) . . . .
C20 C19 C23 O1 -129.00(19) . . . .
