#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/39/4023983.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_4023983
loop_
_publ_author_name
'Mercedes Amat'
'María M. M. Santos'
'Oriol Bassas'
'Núria Llor'
'Carmen Escolano'
'Arantxa Gómez-Esqué'
'Elies Molins'
'Steven M. Allin'
'Vickie McKee'
'Joan Bosch'
_publ_section_title
;
 Straightforward Methodology for the Enantioselective Synthesis of
 Benzo[a]- and Indolo[2,3-a]quinolizidines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5193
_journal_page_last               5201
_journal_paper_doi               10.1021/jo070539g
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C21 H31 N1 O6'
_chemical_formula_sum            'C21 H29 N O6'
_chemical_formula_weight         391.45
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2005-03-10T12:51:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8750(10)
_cell_length_b                   9.8410(10)
_cell_length_c                   23.762(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.4
_cell_measurement_theta_min      12.6
_cell_measurement_wavelength     0.71073
_cell_volume                     2075.3(4)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.839
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_orient_matrix_type
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      0.025698
_diffrn_orient_matrix_UB_12      -0.095541
_diffrn_orient_matrix_UB_13      0.010546
_diffrn_orient_matrix_UB_21      0.108753
_diffrn_orient_matrix_UB_22      0.018549
_diffrn_orient_matrix_UB_23      -0.008146
_diffrn_orient_matrix_UB_31      0.015454
_diffrn_orient_matrix_UB_32      0.029175
_diffrn_orient_matrix_UB_33      0.039887
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.1019
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3689
_diffrn_reflns_theta_full        33.02
_diffrn_reflns_theta_max         33.02
_diffrn_reflns_theta_min         2.24
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9676
_exptl_absorpt_correction_T_min  0.9304
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
        Number of psi-scan sets used was   7
        Theta correction was applied.
        Averaged transmission function was used.
        Fourier smoothing - Window value   3
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.8(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1836
_refine_ls_R_factor_gt           0.056
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1077P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1889
_reflns_number_gt                1952
_reflns_number_total             3689
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070539grom20070315_094441.cif
_cod_data_source_block           jb47
_cod_database_code               4023983
_exptl_absorpt_factor_mur        0.029
_exptl_absorpt_correction_t_ave  0.9539
_diffrn_standards_decay_corr_max 1
_diffrn_standards_decay_corr_min 1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
C1 C 0.1959(4) 0.5937(2) 0.37698(11) 0.0415(6) Uani 1 1 d . . .
H1 H 0.1112 0.6364 0.3573 0.05 Uiso 1 1 calc R . .
C2 C 0.2783(5) 0.4970(2) 0.33447(13) 0.0473(7) Uani 1 1 d . . .
H2 H 0.2991 0.4126 0.3549 0.057 Uiso 1 1 calc R . .
C3 C 0.4314(4) 0.5524(2) 0.31489(11) 0.0427(6) Uani 1 1 d . . .
H3A H 0.5059 0.5355 0.3439 0.051 Uiso 1 1 calc R . .
H3B H 0.4626 0.5038 0.2813 0.051 Uiso 1 1 calc R . .
C4 C 0.4267(4) 0.7025(2) 0.30231(10) 0.0394(5) Uani 1 1 d . . .
C6 C 0.3150(4) 0.9192(2) 0.33002(9) 0.0357(5) Uani 1 1 d . . .
H6 H 0.3054 0.9287 0.2891 0.043 Uiso 1 1 calc R . .
C7 C 0.1623(4) 0.9512(2) 0.35599(10) 0.0406(6) Uani 1 1 d . . .
H7A H 0.1372 1.0459 0.3497 0.049 Uiso 1 1 calc R . .
H7B H 0.085 0.8955 0.3386 0.049 Uiso 1 1 calc R . .
C7A C 0.1691(4) 0.9225(2) 0.41853(10) 0.0375(5) Uani 1 1 d . . .
C8 C 0.1106(4) 1.0123(3) 0.45888(11) 0.0428(6) Uani 1 1 d . . .
H8 H 0.0616 1.091 0.4472 0.051 Uiso 1 1 calc R . .
C9 C 0.1245(5) 0.9857(3) 0.51575(11) 0.0460(7) Uani 1 1 d . . .
C10 C 0.2004(4) 0.8681(3) 0.53385(10) 0.0438(6) Uani 1 1 d . . .
C11 C 0.2628(4) 0.7811(2) 0.49420(11) 0.0405(6) Uani 1 1 d . . .
H11 H 0.317 0.7053 0.506 0.049 Uiso 1 1 calc R . .
C11A C 0.2447(4) 0.8067(2) 0.43640(10) 0.0361(5) Uani 1 1 d . . .
C11B C 0.3086(3) 0.7074(2) 0.39411(9) 0.0349(5) Uani 1 1 d . . .
H11B H 0.3973 0.6642 0.4109 0.042 Uiso 1 1 calc R . .
C12 C 0.1333(6) 0.5187(3) 0.42888(14) 0.0569(9) Uani 1 1 d . . .
H12A H 0.2157 0.4746 0.4485 0.068 Uiso 1 1 calc R . .
H12B H 0.0888 0.5845 0.4543 0.068 Uiso 1 1 calc R . .
C13 C 0.0150(8) 0.4123(4) 0.4135(2) 0.0740(13) Uani 1 1 d . . .
H13A H 0.0626 0.3379 0.3944 0.111 Uiso 1 1 calc R . .
H13B H -0.0594 0.4525 0.3894 0.111 Uiso 1 1 calc R . .
H13C H -0.0327 0.3797 0.4472 0.111 Uiso 1 1 calc R . .
C21 C 0.1758(7) 0.4583(3) 0.28435(15) 0.0633(10) Uani 1 1 d . . .
H21A H 0.2261 0.3895 0.2619 0.076 Uiso 1 1 calc R . .
H21B H 0.0833 0.419 0.2987 0.076 Uiso 1 1 calc R . .
C22 C 0.1375(6) 0.5774(4) 0.24723(16) 0.0628(9) Uani 1 1 d . . .
C23 C 0.2000(13) 0.6887(10) 0.1636(4) 0.115(3) Uani 1 1 d . . .
H23A H 0.2971 0.7147 0.1494 0.172 Uiso 1 1 calc R . .
H23B H 0.1568 0.763 0.1842 0.172 Uiso 1 1 calc R . .
H23C H 0.1352 0.6652 0.1328 0.172 Uiso 1 1 calc R . .
C61 C 0.4395(4) 1.0152(2) 0.34954(11) 0.0421(6) Uani 1 1 d . . .
H61A H 0.4556 1.0039 0.3896 0.05 Uiso 1 1 calc R . .
H61B H 0.5328 0.9927 0.3304 0.05 Uiso 1 1 calc R . .
C91 C 0.0110(8) 1.1944(3) 0.54237(15) 0.0749(15) Uani 1 1 d . . .
H91A H -0.0767 1.1819 0.5193 0.112 Uiso 1 1 calc R . .
H91B H 0.0858 1.2441 0.5217 0.112 Uiso 1 1 calc R . .
H91C H -0.0159 1.2443 0.5756 0.112 Uiso 1 1 calc R . .
C101 C 0.2786(7) 0.7314(4) 0.61102(14) 0.0658(10) Uani 1 1 d . . .
H10A H 0.3826 0.7309 0.5999 0.099 Uiso 1 1 calc R . .
H10B H 0.2288 0.6531 0.5957 0.099 Uiso 1 1 calc R . .
H10C H 0.2721 0.7292 0.6513 0.099 Uiso 1 1 calc R . .
N5 N 0.3567(3) 0.77746(18) 0.34206(8) 0.0365(5) Uani 1 1 d . . .
O4 O 0.4791(4) 0.7541(2) 0.25912(9) 0.0534(6) Uani 1 1 d . . .
O22 O 0.0516(9) 0.6699(5) 0.25719(17) 0.1060(19) Uani 1 1 d . . .
O23 O 0.2161(6) 0.5745(4) 0.19990(16) 0.0870(11) Uani 1 1 d . . .
O61 O 0.4003(5) 1.15291(17) 0.33797(10) 0.0559(8) Uani 1 1 d . . .
H61 H 0.4097 1.1678 0.3042 0.084 Uiso 1 1 calc R . .
O91 O 0.0698(5) 1.0660(2) 0.55793(9) 0.0654(9) Uani 1 1 d . . .
O101 O 0.2083(5) 0.8508(2) 0.59067(9) 0.0583(7) Uani 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
5 2 6
2 3 -12
2 -5 -7
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
C12 C1 C11B 111.5(2) . . ?
C12 C1 C2 113.1(2) . . ?
C11B C1 C2 107.8(3) . . ?
C3 C2 C21 112.0(3) . . ?
C3 C2 C1 113.1(2) . . ?
C21 C2 C1 111.8(3) . . ?
C4 C3 C2 112.5(3) . . ?
O4 C4 N5 122.0(2) . . ?
O4 C4 C3 123.8(2) . . ?
N5 C4 C3 114.2(2) . . ?
N5 C6 C7 110.0(2) . . ?
N5 C6 C61 110.2(2) . . ?
C7 C6 C61 113.2(2) . . ?
C7A C7 C6 108.9(3) . . ?
C11A C7A C8 119.1(2) . . ?
C11A C7A C7 118.2(2) . . ?
C8 C7A C7 122.6(2) . . ?
C9 C8 C7A 121.0(2) . . ?
O91 C9 C8 125.2(3) . . ?
O91 C9 C10 115.0(2) . . ?
C8 C9 C10 119.8(2) . . ?
O101 C10 C11 125.1(3) . . ?
O101 C10 C9 115.5(3) . . ?
C11 C10 C9 119.4(2) . . ?
C10 C11 C11A 120.4(2) . . ?
C7A C11A C11 120.1(2) . . ?
C7A C11A C11B 120.5(2) . . ?
C11 C11A C11B 119.4(2) . . ?
N5 C11B C11A 111.30(18) . . ?
N5 C11B C1 107.6(2) . . ?
C11A C11B C1 113.4(2) . . ?
C13 C12 C1 112.7(3) . . ?
C22 C21 C2 113.1(3) . . ?
O22 C22 O23 121.0(5) . . ?
O22 C22 C21 127.8(5) . . ?
O23 C22 C21 111.2(4) . . ?
O61 C61 C6 110.7(3) . . ?
C4 N5 C6 119.86(19) . . ?
C4 N5 C11B 117.60(18) . . ?
C6 N5 C11B 122.1(2) . . ?
C22 O23 C23 116.4(6) . . ?
C9 O91 C91 117.1(2) . . ?
C10 O101 C101 117.7(3) . . ?
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
C1 C12 1.541(4) . ?
C1 C11B 1.555(4) . ?
C1 C2 1.569(4) . ?
C2 C3 1.536(5) . ?
C2 C21 1.546(5) . ?
C3 C4 1.508(4) . ?
C4 O4 1.236(4) . ?
C4 N5 1.350(3) . ?
C6 N5 1.471(3) . ?
C6 C7 1.522(4) . ?
C6 C61 1.526(4) . ?
C7 C7A 1.514(3) . ?
C7A C11A 1.389(4) . ?
C7A C8 1.404(3) . ?
C8 C9 1.382(4) . ?
C9 O91 1.365(3) . ?
C9 C10 1.407(4) . ?
C10 O101 1.363(3) . ?
C10 C11 1.388(4) . ?
C11 C11A 1.406(3) . ?
C11A C11B 1.512(3) . ?
C11B N5 1.479(3) . ?
C12 C13 1.527(6) . ?
C21 C22 1.506(6) . ?
C22 O22 1.210(7) . ?
C22 O23 1.324(6) . ?
C23 O23 1.423(7) . ?
C61 O61 1.426(3) . ?
C91 O91 1.417(5) . ?
C101 O101 1.415(5) . ?
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
_geom_torsion_publ_flag
C12 C1 C2 C3 -133.0(3) . . . . ?
C11B C1 C2 C3 -9.2(3) . . . . ?
C12 C1 C2 C21 99.4(4) . . . . ?
C11B C1 C2 C21 -136.7(3) . . . . ?
C21 C2 C3 C4 85.3(3) . . . . ?
C1 C2 C3 C4 -42.2(3) . . . . ?
C2 C3 C4 O4 -132.3(4) . . . . ?
C2 C3 C4 N5 46.3(4) . . . . ?
N5 C6 C7 C7A 56.7(3) . . . . ?
C61 C6 C7 C7A -67.0(3) . . . . ?
C6 C7 C7A C11A -41.1(4) . . . . ?
C6 C7 C7A C8 134.9(3) . . . . ?
C11A C7A C8 C9 -1.3(5) . . . . ?
C7 C7A C8 C9 -177.1(3) . . . . ?
C7A C8 C9 O91 -179.2(4) . . . . ?
C7A C8 C9 C10 1.0(6) . . . . ?
O91 C9 C10 O101 0.1(6) . . . . ?
C8 C9 C10 O101 180.0(4) . . . . ?
O91 C9 C10 C11 -178.8(4) . . . . ?
C8 C9 C10 C11 1.1(6) . . . . ?
O101 C10 C11 C11A 178.3(4) . . . . ?
C9 C10 C11 C11A -2.9(5) . . . . ?
C8 C7A C11A C11 -0.5(5) . . . . ?
C7 C7A C11A C11 175.6(3) . . . . ?
C8 C7A C11A C11B 179.7(3) . . . . ?
C7 C7A C11A C11B -4.2(5) . . . . ?
C10 C11 C11A C7A 2.6(5) . . . . ?
C10 C11 C11A C11B -177.7(3) . . . . ?
C7A C11A C11B N5 31.6(4) . . . . ?
C11 C11A C11B N5 -148.1(3) . . . . ?
C7A C11A C11B C1 -89.9(3) . . . . ?
C11 C11A C11B C1 90.4(3) . . . . ?
C12 C1 C11B N5 -177.4(3) . . . . ?
C2 C1 C11B N5 57.9(3) . . . . ?
C12 C1 C11B C11A -53.8(3) . . . . ?
C2 C1 C11B C11A -178.6(2) . . . . ?
C11B C1 C12 C13 176.4(4) . . . . ?
C2 C1 C12 C13 -61.8(5) . . . . ?
C3 C2 C21 C22 -62.0(5) . . . . ?
C1 C2 C21 C22 66.1(5) . . . . ?
C2 C21 C22 O22 -73.5(8) . . . . ?
C2 C21 C22 O23 104.0(5) . . . . ?
N5 C6 C61 O61 179.9(2) . . . . ?
C7 C6 C61 O61 -56.5(3) . . . . ?
O4 C4 N5 C6 11.8(5) . . . . ?
C3 C4 N5 C6 -166.9(3) . . . . ?
O4 C4 N5 C11B -175.4(3) . . . . ?
C3 C4 N5 C11B 6.0(4) . . . . ?
C7 C6 N5 C4 141.4(3) . . . . ?
C61 C6 N5 C4 -93.2(3) . . . . ?
C7 C6 N5 C11B -31.1(3) . . . . ?
C61 C6 N5 C11B 94.3(3) . . . . ?
C11A C11B N5 C4 175.0(3) . . . . ?
C1 C11B N5 C4 -60.2(3) . . . . ?
C11A C11B N5 C6 -12.3(4) . . . . ?
C1 C11B N5 C6 112.5(3) . . . . ?
O22 C22 O23 C23 3.4(10) . . . . ?
C21 C22 O23 C23 -174.4(6) . . . . ?
C8 C9 O91 C91 -8.3(7) . . . . ?
C10 C9 O91 C91 171.5(5) . . . . ?
C11 C10 O101 C101 -3.5(7) . . . . ?
C9 C10 O101 C101 177.7(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 20572806
