#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/02/2210228.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2210228
loop_
_publ_author_name
'Ya-Wen Wang'
'Yu Peng'
_publ_section_title
;Ethyl
 12b-allyl-1-hydroxy-3,6,7,12b-tetrahydro-4H-1,3-dioxolo[4,5-g]pyrido[2,1-a]isoquinoline-2-carboxylate
;
_journal_coeditor_code           FL2046
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3966
_journal_page_last               o3967
_journal_paper_doi               10.1107/S1600536806031977
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C20 H23 N O5'
_chemical_formula_moiety         'C20 H23 N O5'
_chemical_formula_sum            'C20 H23 N O5'
_chemical_formula_weight         357.39
_chemical_name_systematic
;Ethyl
 12b-allyl-1-hydroxy-3,6,7,12b-tetrahydro-4H-1,3-dioxolo[4,5-g]pyrido[2,1-
a]isoquinoline-2-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 99.854(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5365(7)
_cell_length_b                   20.0523(18)
_cell_length_c                   10.6574(9)
_cell_measurement_reflns_used    1800
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.19
_cell_volume                     1797.4(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0535
_diffrn_reflns_av_sigmaI/netI    0.0692
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9495
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.402
_refine_ls_extinction_coef       0.0022(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3350
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.188
_refine_ls_R_factor_all          0.1525
_refine_ls_R_factor_gt           0.0837
_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)+(0.0336P)²+2.3489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.1799
_reflns_number_gt                1915
_reflns_number_total             3350
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2046.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2210228
_cod_database_fobs_code          2210228
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O5 0.3644(3) 0.72684(13) 0.6686(3) 0.0517(8) Uani d . 1
H H5 0.4297 0.7171 0.6235 0.078 Uiso calc R 1
N N1 0.0345(4) 0.62860(15) 0.7403(3) 0.0423(8) Uani d . 1
O O3 0.4766(4) 0.66506(14) 0.4938(3) 0.0602(9) Uani d . 1
O O4 0.3496(4) 0.57247(14) 0.4151(3) 0.0600(9) Uani d . 1
O O2 -0.2179(4) 0.93117(15) 0.6902(4) 0.0810(11) Uani d . 1
O O1 0.0411(4) 0.93451(13) 0.6546(3) 0.0616(9) Uani d . 1
C C4 0.0957(5) 0.81455(18) 0.6949(4) 0.0399(10) Uani d . 1
H H4 0.2013 0.8170 0.6840 0.048 Uiso calc R 1
C C14 0.1324(5) 0.68983(18) 0.7464(4) 0.0387(10) Uani d . 1
C C3 0.0006(5) 0.86979(19) 0.6826(4) 0.0452(10) Uani d . 1
C C5 0.0280(5) 0.75370(18) 0.7247(4) 0.0409(10) Uani d . 1
C C13 0.2449(4) 0.68203(18) 0.6510(4) 0.0396(10) Uani d . 1
C C18 0.3633(5) 0.6268(2) 0.4889(4) 0.0484(11) Uani d . 1
C C15 0.2356(5) 0.6956(2) 0.8804(4) 0.0506(11) Uani d . 1
H H15A 0.3038 0.7344 0.8817 0.061 Uiso calc R 1
H H15B 0.1661 0.7031 0.9421 0.061 Uiso calc R 1
C C12 0.2358(5) 0.63344(19) 0.5618(4) 0.0434(10) Uani d . 1
C C10 -0.0322(5) 0.6102(2) 0.6089(4) 0.0513(11) Uani d . 1
H H10A -0.0831 0.6486 0.5641 0.062 Uiso calc R 1
H H10B -0.1118 0.5756 0.6089 0.062 Uiso calc R 1
C C9 -0.0881(5) 0.6339(2) 0.8199(4) 0.0561(12) Uani d . 1
H H9A -0.0376 0.6424 0.9071 0.067 Uiso calc R 1
H H9B -0.1436 0.5916 0.8184 0.067 Uiso calc R 1
C C2 -0.1523(5) 0.8677(2) 0.7027(5) 0.0561(12) Uani d . 1
C C8 -0.2074(6) 0.6883(2) 0.7777(6) 0.0746(16) Uani d . 1
H H8A -0.2677 0.6973 0.8452 0.090 Uiso calc R 1
H H8B -0.2813 0.6733 0.7036 0.090 Uiso calc R 1
C C7 -0.2206(5) 0.8102(2) 0.7342(5) 0.0692(15) Uani d . 1
H H7 -0.3252 0.8095 0.7480 0.083 Uiso calc R 1
C C11 0.0984(5) 0.5853(2) 0.5430(4) 0.0523(12) Uani d . 1
H H11A 0.0582 0.5802 0.4527 0.063 Uiso calc R 1
H H11B 0.1343 0.5420 0.5769 0.063 Uiso calc R 1
C C1 -0.1059(6) 0.9698(2) 0.6392(5) 0.0648(14) Uani d . 1
H H1A -0.0909 1.0123 0.6828 0.078 Uiso calc R 1
H H1B -0.1440 0.9782 0.5495 0.078 Uiso calc R 1
C C6 -0.1276(5) 0.7521(2) 0.7451(4) 0.0541(12) Uani d . 1
C C20 0.4405(7) 0.4979(3) 0.2711(5) 0.0840(18) Uani d . 1
H H20A 0.4252 0.4631 0.3296 0.126 Uiso calc R 1
H H20B 0.5274 0.4865 0.2287 0.126 Uiso calc R 1
H H20C 0.3455 0.5033 0.2093 0.126 Uiso calc R 1
C C19 0.4770(6) 0.5614(2) 0.3421(5) 0.0728(15) Uani d . 1
H H19A 0.5786 0.5582 0.3988 0.087 Uiso calc R 1
H H19B 0.4819 0.5980 0.2834 0.087 Uiso calc R 1
C C16 0.3354(8) 0.6371(3) 0.9202(6) 0.102(2) Uani d . 1
H H16 0.2845 0.5978 0.8904 0.122 Uiso calc R 1
C C17 0.4534(11) 0.6274(4) 0.9753(7) 0.157(3) Uani d U 1
H H17A 0.5168 0.6627 1.0105 0.189 Uiso calc R 1
H H17B 0.4903 0.5838 0.9871 0.189 Uiso calc R 1
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
C13 O5 H5 109.5
C9 N1 C10 111.9(3)
C9 N1 C14 111.7(3)
C10 N1 C14 112.0(3)
C18 O4 C19 116.1(3)
C2 O2 C1 104.6(3)
C3 O1 C1 104.0(3)
C3 C4 C5 117.6(4)
C3 C4 H4 121.2
C5 C4 H4 121.2
N1 C14 C13 107.6(3)
N1 C14 C15 109.3(3)
C13 C14 C15 107.4(3)
N1 C14 C5 111.8(3)
C13 C14 C5 113.4(3)
C15 C14 C5 107.2(3)
C2 C3 C4 122.1(4)
C2 C3 O1 110.1(4)
C4 C3 O1 127.8(4)
C6 C5 C4 119.9(4)
C6 C5 C14 119.9(3)
C4 C5 C14 120.0(4)
O5 C13 C12 121.9(3)
O5 C13 C14 112.8(3)
C12 C13 C14 125.2(3)
O3 C18 O4 121.5(4)
O3 C18 C12 125.4(4)
O4 C18 C12 113.1(4)
C16 C15 C14 114.6(4)
C16 C15 H15A 108.6
C14 C15 H15A 108.6
C16 C15 H15B 108.6
C14 C15 H15B 108.6
H15A C15 H15B 107.6
C13 C12 C18 119.0(4)
C13 C12 C11 120.3(4)
C18 C12 C11 120.7(4)
N1 C10 C11 109.4(3)
N1 C10 H10A 109.8
C11 C10 H10A 109.8
N1 C10 H10B 109.8
C11 C10 H10B 109.8
H10A C10 H10B 108.2
N1 C9 C8 113.2(4)
N1 C9 H9A 108.9
C8 C9 H9A 108.9
N1 C9 H9B 108.9
C8 C9 H9B 108.9
H9A C9 H9B 107.7
C3 C2 C7 121.9(4)
C3 C2 O2 109.8(4)
C7 C2 O2 128.2(4)
C9 C8 C6 111.8(4)
C9 C8 H8A 109.3
C6 C8 H8A 109.3
C9 C8 H8B 109.3
C6 C8 H8B 109.3
H8A C8 H8B 107.9
C2 C7 C6 117.7(4)
C2 C7 H7 121.2
C6 C7 H7 121.2
C10 C11 C12 110.5(3)
C10 C11 H11A 109.6
C12 C11 H11A 109.6
C10 C11 H11B 109.6
C12 C11 H11B 109.6
H11A C11 H11B 108.1
O2 C1 O1 108.9(3)
O2 C1 H1A 109.9
O1 C1 H1A 109.9
O2 C1 H1B 109.9
O1 C1 H1B 109.9
H1A C1 H1B 108.3
C5 C6 C7 120.8(4)
C5 C6 C8 122.5(4)
C7 C6 C8 116.7(4)
C19 C20 H20A 109.5
C19 C20 H20B 109.5
H20A C20 H20B 109.5
C19 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
O4 C19 C20 106.9(4)
O4 C19 H19A 110.3
C20 C19 H19A 110.3
O4 C19 H19B 110.3
C20 C19 H19B 110.3
H19A C19 H19B 108.6
C17 C16 C15 137.1(7)
C17 C16 H16 111.4
C15 C16 H16 111.4
C16 C17 H17A 120.0
C16 C17 H17B 120.0
H17A C17 H17B 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O5 C13 1.348(4)
O5 H5 0.8200
N1 C9 1.459(5)
N1 C10 1.466(5)
N1 C14 1.480(5)
O3 C18 1.229(5)
O4 C18 1.338(5)
O4 C19 1.458(5)
O2 C2 1.387(5)
O2 C1 1.410(5)
O1 C3 1.389(4)
O1 C1 1.425(5)
C4 C3 1.366(5)
C4 C5 1.409(5)
C4 H4 0.9300
C14 C13 1.521(5)
C14 C15 1.549(5)
C14 C5 1.555(5)
C3 C2 1.359(6)
C5 C6 1.382(6)
C13 C12 1.354(5)
C18 C12 1.447(6)
C15 C16 1.469(6)
C15 H15A 0.9700
C15 H15B 0.9700
C12 C11 1.505(5)
C10 C11 1.501(6)
C10 H10A 0.9700
C10 H10B 0.9700
C9 C8 1.509(6)
C9 H9A 0.9700
C9 H9B 0.9700
C2 C7 1.359(6)
C8 C6 1.517(6)
C8 H8A 0.9700
C8 H8B 0.9700
C7 C6 1.405(6)
C7 H7 0.9300
C11 H11A 0.9700
C11 H11B 0.9700
C1 H1A 0.9700
C1 H1B 0.9700
C20 C19 1.486(6)
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
C19 H19A 0.9700
C19 H19B 0.9700
C16 C17 1.093(8)
C16 H16 0.9300
C17 H17A 0.9300
C17 H17B 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O5 H5 O3 0.82 1.83 2.556(4) 146.9
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
C9 N1 C14 C13 -174.5(3)
C10 N1 C14 C13 -48.0(4)
C9 N1 C14 C15 69.1(4)
C10 N1 C14 C15 -164.4(3)
C9 N1 C14 C5 -49.4(4)
C10 N1 C14 C5 77.1(4)
C5 C4 C3 C2 2.5(6)
C5 C4 C3 O1 179.6(4)
C1 O1 C3 C2 -8.9(5)
C1 O1 C3 C4 173.6(4)
C3 C4 C5 C6 -2.5(6)
C3 C4 C5 C14 -177.0(3)
N1 C14 C5 C6 21.5(5)
C13 C14 C5 C6 143.4(4)
C15 C14 C5 C6 -98.2(4)
N1 C14 C5 C4 -163.9(3)
C13 C14 C5 C4 -42.1(5)
C15 C14 C5 C4 76.3(4)
N1 C14 C13 O5 -165.2(3)
C15 C14 C13 O5 -47.7(4)
C5 C14 C13 O5 70.6(4)
N1 C14 C13 C12 10.8(5)
C15 C14 C13 C12 128.3(4)
C5 C14 C13 C12 -113.4(4)
C19 O4 C18 O3 0.4(6)
C19 O4 C18 C12 -178.0(4)
N1 C14 C15 C16 55.0(5)
C13 C14 C15 C16 -61.4(5)
C5 C14 C15 C16 176.4(4)
O5 C13 C12 C18 4.0(6)
C14 C13 C12 C18 -171.7(4)
O5 C13 C12 C11 -178.6(4)
C14 C13 C12 C11 5.7(6)
O3 C18 C12 C13 -5.7(7)
O4 C18 C12 C13 172.6(4)
O3 C18 C12 C11 176.9(4)
O4 C18 C12 C11 -4.8(6)
C9 N1 C10 C11 -162.8(3)
C14 N1 C10 C11 70.8(4)
C10 N1 C9 C8 -63.4(5)
C14 N1 C9 C8 63.1(5)
C4 C3 C2 C7 -1.1(7)
O1 C3 C2 C7 -178.8(4)
C4 C3 C2 O2 176.9(4)
O1 C3 C2 O2 -0.7(5)
C1 O2 C2 C3 10.2(5)
C1 O2 C2 C7 -171.9(5)
N1 C9 C8 C6 -44.0(6)
C3 C2 C7 C6 -0.2(8)
O2 C2 C7 C6 -177.9(5)
N1 C10 C11 C12 -49.7(5)
C13 C12 C11 C10 13.8(5)
C18 C12 C11 C10 -168.8(4)
C2 O2 C1 O1 -15.8(5)
C3 O1 C1 O2 15.3(5)
C4 C5 C6 C7 1.2(7)
C14 C5 C6 C7 175.8(4)
C4 C5 C6 C8 -179.9(4)
C14 C5 C6 C8 -5.4(7)
C2 C7 C6 C5 0.1(8)
C2 C7 C6 C8 -178.8(5)
C9 C8 C6 C5 15.8(7)
C9 C8 C6 C7 -165.3(5)
C18 O4 C19 C20 178.2(4)
C14 C15 C16 C17 144.5(11)
