#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/89/2228993.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_2228993
loop_
_publ_author_name
'Chitra Devi, G.'
'Bhaskaran, Sundari'
'Usha, G.'
'Murugan, G.'
'Bakthadoss, M.'
_publ_section_title
;
 Methyl
 3-(4-fluorophenyl)-1-methyl-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b]pyrrole-3a-carboxylate
;
_journal_coeditor_code           BX2338
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o349
_journal_paper_doi               10.1107/S1600536810054036
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H20 F N O3'
_chemical_formula_moiety         'C20 H20 F N O3'
_chemical_formula_sum            'C20 H20 F N O3'
_chemical_formula_weight         341.37
_chemical_name_systematic
;
Methyl 3-(4-fluorophenyl)-1-methyl-1,2,3,3a,4,9b-
hexahydrochromeno[4,3-b]pyrrole-3a-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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.535(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4519(4)
_cell_length_b                   20.6778(8)
_cell_length_c                   7.8508(3)
_cell_measurement_reflns_used    4237
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      2
_cell_volume                     1696.12(11)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT and XPREP (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97(Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ scan'
_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  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16737
_diffrn_reflns_theta_full        28.37
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.175
_refine_ls_extinction_coef       0.013(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.806
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4237
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.806
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0447
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.2189
_reflns_number_gt                2844
_reflns_number_total             4237
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bx2338.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228993
_cod_database_fobs_code          2228993
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C20 0.1861(2) 0.22098(11) 0.9717(3) 0.0645(6) Uani d . 1 . .
H H20A 0.1703 0.2651 0.9389 0.097 Uiso calc R 1 . .
H H20B 0.2338 0.2201 1.0780 0.097 Uiso calc R 1 . .
H H20C 0.1060 0.1990 0.9845 0.097 Uiso calc R 1 . .
O O1 0.53935(13) 0.05675(7) 0.87998(17) 0.0559(4) Uani d . 1 . .
F F -0.01102(13) -0.15643(6) 0.7317(2) 0.0775(5) Uani d . 1 . .
C C1 0.63732(18) 0.20543(10) 0.6667(2) 0.0505(5) Uani d . 1 . .
H H1 0.6080 0.2352 0.5858 0.061 Uiso calc R 1 . .
C C2 0.7536(2) 0.21569(12) 0.7493(3) 0.0655(6) Uani d . 1 . .
H H2 0.8025 0.2518 0.7236 0.079 Uiso calc R 1 . .
C C3 0.7969(2) 0.17199(14) 0.8701(3) 0.0737(7) Uani d . 1 . .
H H3 0.8757 0.1785 0.9253 0.088 Uiso calc R 1 . .
C C4 0.7248(2) 0.11893(12) 0.9099(3) 0.0640(6) Uani d . 1 . .
H H4 0.7545 0.0898 0.9922 0.077 Uiso calc R 1 . .
C C5 0.60721(17) 0.10867(9) 0.8271(2) 0.0458(4) Uani d . 1 . .
C C6 0.42920(17) 0.03806(8) 0.7786(2) 0.0422(4) Uani d . 1 . .
H H6A 0.3763 0.0094 0.8447 0.051 Uiso calc R 1 . .
H H6B 0.4569 0.0143 0.6796 0.051 Uiso calc R 1 . .
C C7 0.35015(15) 0.09573(8) 0.72016(18) 0.0357(4) Uani d . 1 . .
C C8 0.43498(15) 0.14033(8) 0.61491(19) 0.0359(4) Uani d . 1 . .
H H8 0.3916 0.1818 0.5955 0.043 Uiso calc R 1 . .
C C9 0.56300(16) 0.15160(8) 0.7018(2) 0.0398(4) Uani d . 1 . .
C C10 0.24295(16) 0.07657(8) 0.58563(19) 0.0383(4) Uani d . 1 . .
H H10 0.1776 0.1105 0.5884 0.046 Uiso calc R 1 . .
C C11 0.30986(18) 0.08318(10) 0.4144(2) 0.0485(5) Uani d . 1 . .
H H11A 0.3104 0.0420 0.3554 0.058 Uiso calc R 1 . .
H H11B 0.2657 0.1146 0.3425 0.058 Uiso calc R 1 . .
C C12 0.17597(15) 0.01306(8) 0.62225(18) 0.0373(4) Uani d . 1 . .
C C13 0.06850(16) 0.01298(9) 0.7231(2) 0.0440(4) Uani d . 1 . .
H H13 0.0382 0.0520 0.7649 0.053 Uiso calc R 1 . .
C C14 0.00570(18) -0.04361(10) 0.7628(2) 0.0515(5) Uani d . 1 . .
H H14 -0.0650 -0.0433 0.8323 0.062 Uiso calc R 1 . .
C C15 0.05039(18) -0.09990(9) 0.6970(2) 0.0503(5) Uani d . 1 . .
C C16 0.1548(2) -0.10261(9) 0.5965(3) 0.0540(5) Uani d . 1 . .
H H16 0.1828 -0.1418 0.5532 0.065 Uiso calc R 1 . .
C C17 0.21785(17) -0.04557(9) 0.5604(2) 0.0475(4) Uani d . 1 . .
H H17 0.2898 -0.0467 0.4932 0.057 Uiso calc R 1 . .
C C18 0.49406(18) 0.14114(10) 0.3144(2) 0.0501(5) Uani d . 1 . .
H H18A 0.4949 0.1146 0.2141 0.075 Uiso calc R 1 . .
H H18B 0.5799 0.1542 0.3444 0.075 Uiso calc R 1 . .
H H18C 0.4424 0.1788 0.2925 0.075 Uiso calc R 1 . .
C C19 0.28728(16) 0.12722(8) 0.87041(19) 0.0397(4) Uani d . 1 . .
N N 0.44108(14) 0.10458(7) 0.45389(16) 0.0395(4) Uani d . 1 . .
O O2 0.25895(16) 0.09942(7) 0.99746(16) 0.0637(5) Uani d . 1 . .
O O3 0.25839(14) 0.18923(6) 0.84246(17) 0.0556(4) Uani d . 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'
F F 0.0171 0.0103 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 C20 H20A . . 109.5 ?
O3 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
O3 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C5 O1 C6 . . 117.45(13) ?
C2 C1 C9 . . 121.4(2) ?
C2 C1 H1 . . 119.3 ?
C9 C1 H1 . . 119.3 ?
C3 C2 C1 . . 119.4(2) ?
C3 C2 H2 . . 120.3 ?
C1 C2 H2 . . 120.3 ?
C2 C3 C4 . . 120.6(2) ?
C2 C3 H3 . . 119.7 ?
C4 C3 H3 . . 119.7 ?
C3 C4 C5 . . 119.9(2) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
O1 C5 C4 . . 116.08(17) ?
O1 C5 C9 . . 123.58(16) ?
C4 C5 C9 . . 120.30(18) ?
O1 C6 C7 . . 112.27(14) ?
O1 C6 H6A . . 109.1 ?
C7 C6 H6A . . 109.1 ?
O1 C6 H6B . . 109.1 ?
C7 C6 H6B . . 109.1 ?
H6A C6 H6B . . 107.9 ?
C19 C7 C6 . . 110.33(13) ?
C19 C7 C8 . . 115.48(13) ?
C6 C7 C8 . . 108.52(13) ?
C19 C7 C10 . . 108.43(13) ?
C6 C7 C10 . . 112.26(13) ?
C8 C7 C10 . . 101.62(12) ?
N C8 C9 . . 114.21(13) ?
N C8 C7 . . 101.54(12) ?
C9 C8 C7 . . 111.63(13) ?
N C8 H8 . . 109.7 ?
C9 C8 H8 . . 109.7 ?
C7 C8 H8 . . 109.7 ?
C1 C9 C5 . . 118.24(16) ?
C1 C9 C8 . . 122.01(16) ?
C5 C9 C8 . . 119.69(15) ?
C12 C10 C11 . . 117.71(14) ?
C12 C10 C7 . . 114.52(12) ?
C11 C10 C7 . . 103.45(12) ?
C12 C10 H10 . . 106.8 ?
C11 C10 H10 . . 106.8 ?
C7 C10 H10 . . 106.8 ?
N C11 C10 . . 106.67(12) ?
N C11 H11A . . 110.4 ?
C10 C11 H11A . . 110.4 ?
N C11 H11B . . 110.4 ?
C10 C11 H11B . . 110.4 ?
H11A C11 H11B . . 108.6 ?
C17 C12 C13 . . 117.85(16) ?
C17 C12 C10 . . 122.69(15) ?
C13 C12 C10 . . 119.46(15) ?
C14 C13 C12 . . 121.66(17) ?
C14 C13 H13 . . 119.2 ?
C12 C13 H13 . . 119.2 ?
C15 C14 C13 . . 117.96(16) ?
C15 C14 H14 . . 121.0 ?
C13 C14 H14 . . 121.0 ?
C14 C15 C16 . . 122.85(17) ?
C14 C15 F . . 119.26(17) ?
C16 C15 F . . 117.89(17) ?
C15 C16 C17 . . 118.42(17) ?
C15 C16 H16 . . 120.8 ?
C17 C16 H16 . . 120.8 ?
C12 C17 C16 . . 121.23(17) ?
C12 C17 H17 . . 119.4 ?
C16 C17 H17 . . 119.4 ?
N C18 H18A . . 109.5 ?
N C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
N C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
O2 C19 O3 . . 122.65(16) ?
O2 C19 C7 . . 124.48(17) ?
O3 C19 C7 . . 112.74(13) ?
C18 N C8 . . 114.43(14) ?
C18 N C11 . . 111.78(13) ?
C8 N C11 . . 105.79(13) ?
C19 O3 C20 . . 116.29(15) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C20 O3 . 1.440(2) ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
O1 C5 . 1.358(2) ?
O1 C6 . 1.435(2) ?
F C15 . 1.364(2) ?
C1 C2 . 1.379(3) ?
C1 C9 . 1.389(2) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.378(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.371(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.391(3) ?
C4 H4 . 0.9300 ?
C5 C9 . 1.395(3) ?
C6 C7 . 1.515(2) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C19 . 1.513(2) ?
C7 C8 . 1.536(2) ?
C7 C10 . 1.570(2) ?
C8 N . 1.467(2) ?
C8 C9 . 1.504(2) ?
C8 H8 . 0.9800 ?
C10 C12 . 1.519(2) ?
C10 C11 . 1.538(2) ?
C10 H10 . 0.9800 ?
C11 N . 1.466(2) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C17 . 1.382(3) ?
C12 C13 . 1.392(2) ?
C13 C14 . 1.381(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.361(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.365(3) ?
C16 C17 . 1.384(3) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
C18 N . 1.453(2) ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 O2 . 1.1953(19) ?
C19 O3 . 1.334(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C6 H6B N . 0.97 2.58 2.902(2) 100
C8 H8 O3 . 0.98 2.42 2.792(2) 102
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 C1 C2 C3 . . . . -0.5(3) ?
C1 C2 C3 C4 . . . . -0.6(4) ?
C2 C3 C4 C5 . . . . 0.4(4) ?
C6 O1 C5 C4 . . . . -169.32(16) ?
C6 O1 C5 C9 . . . . 12.9(3) ?
C3 C4 C5 O1 . . . . -176.91(19) ?
C3 C4 C5 C9 . . . . 1.0(3) ?
C5 O1 C6 C7 . . . . -42.6(2) ?
O1 C6 C7 C19 . . . . -68.27(17) ?
O1 C6 C7 C8 . . . . 59.16(17) ?
O1 C6 C7 C10 . . . . 170.67(13) ?
C19 C7 C8 N . . . . -160.23(13) ?
C6 C7 C8 N . . . . 75.34(14) ?
C10 C7 C8 N . . . . -43.13(15) ?
C19 C7 C8 C9 . . . . 77.68(16) ?
C6 C7 C8 C9 . . . . -46.75(17) ?
C10 C7 C8 C9 . . . . -165.22(13) ?
C2 C1 C9 C5 . . . . 1.8(3) ?
C2 C1 C9 C8 . . . . 178.95(16) ?
O1 C5 C9 C1 . . . . 175.64(16) ?
C4 C5 C9 C1 . . . . -2.1(3) ?
O1 C5 C9 C8 . . . . -1.5(3) ?
C4 C5 C9 C8 . . . . -179.23(16) ?
N C8 C9 C1 . . . . 88.40(19) ?
C7 C8 C9 C1 . . . . -157.13(15) ?
N C8 C9 C5 . . . . -94.54(18) ?
C7 C8 C9 C5 . . . . 19.9(2) ?
C19 C7 C10 C12 . . . . -82.09(17) ?
C6 C7 C10 C12 . . . . 40.05(19) ?
C8 C7 C10 C12 . . . . 155.80(13) ?
C19 C7 C10 C11 . . . . 148.52(14) ?
C6 C7 C10 C11 . . . . -89.33(16) ?
C8 C7 C10 C11 . . . . 26.42(16) ?
C12 C10 C11 N . . . . -127.87(15) ?
C7 C10 C11 N . . . . -0.45(18) ?
C11 C10 C12 C17 . . . . 31.4(2) ?
C7 C10 C12 C17 . . . . -90.51(19) ?
C11 C10 C12 C13 . . . . -149.15(15) ?
C7 C10 C12 C13 . . . . 88.96(18) ?
C17 C12 C13 C14 . . . . 0.8(2) ?
C10 C12 C13 C14 . . . . -178.74(15) ?
C12 C13 C14 C15 . . . . -1.4(3) ?
C13 C14 C15 C16 . . . . 0.9(3) ?
C13 C14 C15 F . . . . -178.91(17) ?
C14 C15 C16 C17 . . . . 0.1(3) ?
F C15 C16 C17 . . . . 179.98(17) ?
C13 C12 C17 C16 . . . . 0.4(3) ?
C10 C12 C17 C16 . . . . 179.85(16) ?
C15 C16 C17 C12 . . . . -0.8(3) ?
C6 C7 C19 O2 . . . . -28.0(2) ?
C8 C7 C19 O2 . . . . -151.46(17) ?
C10 C7 C19 O2 . . . . 95.34(19) ?
C6 C7 C19 O3 . . . . 156.20(14) ?
C8 C7 C19 O3 . . . . 32.72(18) ?
C10 C7 C19 O3 . . . . -80.49(16) ?
C9 C8 N C18 . . . . -71.69(18) ?
C7 C8 N C18 . . . . 168.03(13) ?
C9 C8 N C11 . . . . 164.82(14) ?
C7 C8 N C11 . . . . 44.53(15) ?
C10 C11 N C18 . . . . -152.67(15) ?
C10 C11 N C8 . . . . -27.52(18) ?
O2 C19 O3 C20 . . . . -2.3(3) ?
C7 C19 O3 C20 . . . . 173.64(16) ?
