#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/39/4023981.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_4023981
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_formula_sum            'C19 H25 N O6'
_chemical_formula_weight         363.40
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.4330(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.2845(7)
_cell_length_b                   5.9240(5)
_cell_length_c                   16.6375(13)
_cell_measurement_reflns_used    3848
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.79
_cell_measurement_theta_min      2.20
_cell_volume                     914.80(13)
_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      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7877
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.78
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.932327
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2344
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0328
_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)+(0.0426P)²+0.1155P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0838
_reflns_number_gt                2082
_reflns_number_total             2344
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070539grom20070315_094404.cif
_cod_data_source_block           sma47
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023981
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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 0.15115(18) 0.4405(3) 0.58374(9) 0.0455(4) Uani 1 1 d . . .
C1 C 0.2075(3) 0.4829(4) 0.66216(13) 0.0432(5) Uani 1 1 d . . .
H1A H 0.2981 0.3975 0.6715 0.052 Uiso 1 1 calc R . .
H1B H 0.1376 0.4359 0.7029 0.052 Uiso 1 1 calc R . .
C2 C 0.2362(2) 0.7372(4) 0.66835(11) 0.0295(4) Uani 1 1 d . . .
H2 H 0.3319 0.7643 0.6955 0.035 Uiso 1 1 calc R . .
C21 C 0.1196(2) 0.8705(4) 0.71097(10) 0.0303(4) Uani 1 1 d . . .
H21A H 0.1235 1.0302 0.6937 0.036 Uiso 1 1 calc R . .
H21B H 0.0239 0.8099 0.6948 0.036 Uiso 1 1 calc R . .
C22 C 0.13705(19) 0.8589(4) 0.80156(11) 0.0284(4) Uani 1 1 d . . .
C23 C 0.23036(19) 1.0105(4) 0.84104(11) 0.0286(4) Uani 1 1 d . . .
H23 H 0.2791 1.1209 0.8105 0.034 Uiso 1 1 calc R . .
C24 C 0.25318(19) 1.0030(4) 0.92364(11) 0.0282(4) Uani 1 1 d . . .
O21 O 0.33988(15) 1.1468(3) 0.96715(8) 0.0366(4) Uani 1 1 d . . .
C28 C 0.4150(2) 1.3138(4) 0.92331(13) 0.0411(5) Uani 1 1 d . . .
H28A H 0.4731 1.4062 0.9606 0.062 Uiso 1 1 calc R . .
H28B H 0.3455 1.4100 0.8942 0.062 Uiso 1 1 calc R . .
H28C H 0.4780 1.2401 0.8849 0.062 Uiso 1 1 calc R . .
C25 C 0.18308(19) 0.8362(4) 0.96893(10) 0.0281(4) Uani 1 1 d . . .
O22 O 0.21366(14) 0.8396(3) 1.04997(7) 0.0345(3) Uani 1 1 d . . .
C29 C 0.1554(2) 0.6588(4) 1.09575(12) 0.0410(5) Uani 1 1 d . . .
H29A H 0.1833 0.6779 1.1525 0.061 Uiso 1 1 calc R . .
H29B H 0.1927 0.5148 1.0762 0.061 Uiso 1 1 calc R . .
H29C H 0.0501 0.6598 1.0900 0.061 Uiso 1 1 calc R . .
C26 C 0.0903(2) 0.6867(4) 0.93067(11) 0.0318(4) Uani 1 1 d . . .
H26 H 0.0423 0.5748 0.9609 0.038 Uiso 1 1 calc R . .
C27 C 0.0666(2) 0.6997(4) 0.84688(11) 0.0310(4) Uani 1 1 d . . .
H27 H 0.0013 0.5977 0.8211 0.037 Uiso 1 1 calc R . .
N1 N 0.24318(16) 0.7962(3) 0.58328(9) 0.0281(4) Uani 1 1 d . . .
C3 C 0.3432(2) 0.9392(3) 0.55479(11) 0.0274(4) Uani 1 1 d . . .
O32 O 0.42399(14) 1.0460(3) 0.60058(8) 0.0371(4) Uani 1 1 d . . .
C4 C 0.35397(19) 0.9571(3) 0.46458(10) 0.0279(4) Uani 1 1 d . . .
H4A H 0.4491 0.8981 0.4492 0.033 Uiso 1 1 calc R . .
H4B H 0.3506 1.1188 0.4497 0.033 Uiso 1 1 calc R . .
C5 C 0.2375(2) 0.8325(4) 0.41529(11) 0.0290(4) Uani 1 1 d . . .
H5 H 0.1466 0.9231 0.4158 0.035 Uiso 1 1 calc R . .
C51 C 0.2839(2) 0.8056(4) 0.32825(11) 0.0348(5) Uani 1 1 d . . .
H51A H 0.3782 0.7274 0.3278 0.042 Uiso 1 1 calc R . .
H51B H 0.2129 0.7097 0.2989 0.042 Uiso 1 1 calc R . .
C52 C 0.2966(2) 1.0272(4) 0.28536(11) 0.0332(4) Uani 1 1 d . . .
O51 O 0.22392(18) 1.1919(3) 0.29701(10) 0.0534(5) Uani 1 1 d . . .
O52 O 0.39923(16) 1.0232(3) 0.23064(9) 0.0439(4) Uani 1 1 d . . .
C53 C 0.4106(3) 1.2251(5) 0.18200(15) 0.0529(7) Uani 1 1 d . . .
H53A H 0.4886 1.2065 0.1439 0.079 Uiso 1 1 calc R . .
H53B H 0.4314 1.3550 0.2169 0.079 Uiso 1 1 calc R . .
H53C H 0.3196 1.2503 0.1523 0.079 Uiso 1 1 calc R . .
C6 C 0.2097(2) 0.6037(4) 0.45379(11) 0.0324(4) Uani 1 1 d . . .
H6A H 0.1388 0.5176 0.4206 0.039 Uiso 1 1 calc R . .
H6B H 0.3003 0.5158 0.4574 0.039 Uiso 1 1 calc R . .
C7 C 0.1523(2) 0.6413(4) 0.53678(11) 0.0304(4) Uani 1 1 d . . .
H7 H 0.0523 0.7038 0.5321 0.037 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C1 O1 C7 110.48(17) . . ?
O1 C1 C2 107.21(18) . . ?
N1 C2 C21 112.03(16) . . ?
N1 C2 C1 100.47(17) . . ?
C21 C2 C1 114.52(18) . . ?
C22 C21 C2 112.29(16) . . ?
C27 C22 C23 118.53(17) . . ?
C27 C22 C21 122.25(18) . . ?
C23 C22 C21 119.20(17) . . ?
C24 C23 C22 121.49(18) . . ?
O21 C24 C23 125.36(18) . . ?
O21 C24 C25 115.26(15) . . ?
C23 C24 C25 119.38(18) . . ?
C24 O21 C28 116.85(15) . . ?
O22 C25 C26 125.06(18) . . ?
O22 C25 C24 115.34(17) . . ?
C26 C25 C24 119.60(16) . . ?
C25 O22 C29 116.20(16) . . ?
C25 C26 C27 120.12(19) . . ?
C22 C27 C26 120.86(18) . . ?
C3 N1 C7 127.08(15) . . ?
C3 N1 C2 122.49(15) . . ?
C7 N1 C2 108.97(15) . . ?
O32 C3 N1 121.24(17) . . ?
O32 C3 C4 121.64(17) . . ?
N1 C3 C4 117.10(16) . . ?
C3 C4 C5 115.80(15) . . ?
C6 C5 C51 111.08(17) . . ?
C6 C5 C4 109.16(15) . . ?
C51 C5 C4 110.19(16) . . ?
C52 C51 C5 112.71(18) . . ?
O51 C52 O52 122.5(2) . . ?
O51 C52 C51 125.55(18) . . ?
O52 C52 C51 111.99(18) . . ?
C52 O52 C53 115.44(18) . . ?
C7 C6 C5 108.71(16) . . ?
O1 C7 N1 104.29(14) . . ?
O1 C7 C6 112.74(18) . . ?
N1 C7 C6 111.45(16) . . ?
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
O1 C1 1.416(3) . ?
O1 C7 1.423(3) . ?
C1 C2 1.533(3) . ?
C2 N1 1.461(2) . ?
C2 C21 1.528(3) . ?
C21 C22 1.513(2) . ?
C22 C27 1.382(3) . ?
C22 C23 1.400(3) . ?
C23 C24 1.386(2) . ?
C24 O21 1.367(2) . ?
C24 C25 1.411(3) . ?
O21 C28 1.422(3) . ?
C25 O22 1.371(2) . ?
C25 C26 1.380(3) . ?
O22 C29 1.428(3) . ?
C26 C27 1.408(3) . ?
N1 C3 1.352(2) . ?
N1 C7 1.456(2) . ?
C3 O32 1.231(2) . ?
C3 C4 1.510(2) . ?
C4 C5 1.531(3) . ?
C5 C6 1.524(3) . ?
C5 C51 1.530(2) . ?
C51 C52 1.501(3) . ?
C52 O51 1.204(3) . ?
C52 O52 1.335(2) . ?
O52 C53 1.449(3) . ?
C6 C7 1.509(3) . ?
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
C7 O1 C1 C2 4.9(2) . . . . ?
O1 C1 C2 N1 -20.5(2) . . . . ?
O1 C1 C2 C21 99.7(2) . . . . ?
N1 C2 C21 C22 -164.68(16) . . . . ?
C1 C2 C21 C22 81.7(2) . . . . ?
C2 C21 C22 C27 -93.6(2) . . . . ?
C2 C21 C22 C23 84.8(2) . . . . ?
C27 C22 C23 C24 0.2(3) . . . . ?
C21 C22 C23 C24 -178.21(18) . . . . ?
C22 C23 C24 O21 -178.62(18) . . . . ?
C22 C23 C24 C25 1.2(3) . . . . ?
C23 C24 O21 C28 -1.6(3) . . . . ?
C25 C24 O21 C28 178.56(18) . . . . ?
O21 C24 C25 O22 -1.0(2) . . . . ?
C23 C24 C25 O22 179.08(17) . . . . ?
O21 C24 C25 C26 178.32(18) . . . . ?
C23 C24 C25 C26 -1.6(3) . . . . ?
C26 C25 O22 C29 6.7(3) . . . . ?
C24 C25 O22 C29 -173.96(18) . . . . ?
O22 C25 C26 C27 179.73(18) . . . . ?
C24 C25 C26 C27 0.4(3) . . . . ?
C23 C22 C27 C26 -1.4(3) . . . . ?
C21 C22 C27 C26 177.01(19) . . . . ?
C25 C26 C27 C22 1.0(3) . . . . ?
C21 C2 N1 C3 100.2(2) . . . . ?
C1 C2 N1 C3 -137.8(2) . . . . ?
C21 C2 N1 C7 -92.8(2) . . . . ?
C1 C2 N1 C7 29.3(2) . . . . ?
C7 N1 C3 O32 -172.54(19) . . . . ?
C2 N1 C3 O32 -7.9(3) . . . . ?
C7 N1 C3 C4 5.8(3) . . . . ?
C2 N1 C3 C4 170.43(17) . . . . ?
O32 C3 C4 C5 -174.38(18) . . . . ?
N1 C3 C4 C5 7.3(3) . . . . ?
C3 C4 C5 C6 -41.3(2) . . . . ?
C3 C4 C5 C51 -163.56(17) . . . . ?
C6 C5 C51 C52 173.67(17) . . . . ?
C4 C5 C51 C52 -65.2(2) . . . . ?
C5 C51 C52 O51 -32.4(3) . . . . ?
C5 C51 C52 O52 148.11(17) . . . . ?
O51 C52 O52 C53 -4.3(3) . . . . ?
C51 C52 O52 C53 175.26(19) . . . . ?
C51 C5 C6 C7 -175.24(16) . . . . ?
C4 C5 C6 C7 63.0(2) . . . . ?
C1 O1 C7 N1 13.2(2) . . . . ?
C1 O1 C7 C6 134.26(19) . . . . ?
C3 N1 C7 O1 138.86(19) . . . . ?
C2 N1 C7 O1 -27.5(2) . . . . ?
C3 N1 C7 C6 16.9(3) . . . . ?
C2 N1 C7 C6 -149.40(17) . . . . ?
C5 C6 C7 O1 -167.77(15) . . . . ?
C5 C6 C7 N1 -50.9(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10033246
