#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/51/2205146.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_2205146
loop_
_publ_author_name
K.Ravikumar
B.Sridhar
'M. Mahesh'
'V. V. Narayana Reddy'
_publ_section_title
;
 A diastereoisomer of pyrano[3,2-c]quinoline
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o461
_journal_page_last               o463
_journal_paper_doi               10.1107/S1600536805002448
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C18 H18 N2 O3'
_chemical_formula_moiety         'C18 H18 N2 O3'
_chemical_formula_sum            'C18 H18 N2 O3'
_chemical_formula_weight         310.34
_chemical_name_systematic
;
5-(4-nitrophenyl)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline
;
_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
_cell_angle_alpha                98.039(2)
_cell_angle_beta                 115.157(2)
_cell_angle_gamma                104.092(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5001(10)
_cell_length_b                   9.8823(10)
_cell_length_c                   9.9403(10)
_cell_measurement_reflns_used    2569
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.68
_cell_measurement_theta_min      2.21
_cell_volume                     787.18(14)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       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  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0244
_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       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7650
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.21
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.159
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0610
_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)+(0.0514P)²+0.2373P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1386
_reflns_number_gt                2344
_reflns_number_total             2770
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz6039.cif
_cod_data_source_block           I
_cod_database_code               2205146
_cod_database_fobs_code          2205146
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
N1 0.5979(3) 0.8189(2) 1.1103(2) 0.0633(6) Uani d . 1 N
H1N 0.700(3) 0.845(3) 1.171(3) 0.068(8) Uiso d . 1 H
N2 0.9753(2) 0.9282(2) 0.7131(2) 0.0614(5) Uani d . 1 N
O1 0.2223(2) 0.49447(16) 0.88797(18) 0.0605(4) Uani d . 1 O
O2 1.0328(3) 0.8449(2) 0.6707(3) 0.0950(7) Uani d . 1 O
O3 1.0069(2) 1.0536(2) 0.7075(2) 0.0857(6) Uani d . 1 O
C1 0.1396(4) 0.4255(3) 0.7255(3) 0.0763(8) Uani d . 1 C
H1A 0.0376 0.4462 0.6764 0.092 Uiso calc R 1 H
H1B 0.1117 0.3212 0.7080 0.092 Uiso calc R 1 H
C2 0.2467(4) 0.4781(3) 0.6543(3) 0.0767(8) Uani d . 1 C
H2A 0.1876 0.4319 0.5438 0.092 Uiso calc R 1 H
H2B 0.3460 0.4525 0.6988 0.092 Uiso calc R 1 H
C3 0.2927(3) 0.6409(3) 0.6840(3) 0.0616(6) Uani d . 1 C
H3A 0.1952 0.6643 0.6241 0.074 Uiso calc R 1 H
H3B 0.3727 0.6757 0.6495 0.074 Uiso calc R 1 H
C4 0.3654(3) 0.7188(2) 0.8548(2) 0.0474(5) Uani d . 1 C
H4 0.3664 0.8190 0.8623 0.057 Uiso calc R 1 H
C5 0.5427(3) 0.7245(2) 0.9584(2) 0.0498(5) Uani d . 1 C
H5 0.5411 0.6267 0.9675 0.060 Uiso calc R 1 H
C6 0.4998(3) 0.7882(3) 1.1804(3) 0.0539(6) Uani d . 1 C
C7 0.5660(3) 0.8426(3) 1.3395(3) 0.0720(7) Uani d . 1 C
H7 0.6772 0.8989 1.3992 0.086 Uiso calc R 1 H
C8 0.4692(4) 0.8142(3) 1.4090(3) 0.0752(8) Uani d . 1 C
H8 0.5155 0.8502 1.5156 0.090 Uiso calc R 1 H
C9 0.3040(3) 0.7331(3) 1.3229(3) 0.0682(7) Uani d . 1 C
H9 0.2387 0.7136 1.3706 0.082 Uiso calc R 1 H
C10 0.2373(3) 0.6814(2) 1.1663(3) 0.0563(6) Uani d . 1 C
H10 0.1252 0.6279 1.1079 0.068 Uiso calc R 1 H
C11 0.3321(3) 0.7064(2) 1.0918(2) 0.0478(5) Uani d . 1 C
C12 0.2562(3) 0.6479(2) 0.9197(2) 0.0486(5) Uani d . 1 C
H12 0.1511 0.6656 0.8710 0.058 Uiso calc R 1 H
C13 0.6592(3) 0.7803(2) 0.8970(2) 0.0478(5) Uani d . 1 C
C14 0.7181(3) 0.6864(2) 0.8361(3) 0.0577(6) Uani d . 1 C
H14 0.6877 0.5897 0.8367 0.069 Uiso calc R 1 H
C15 0.8203(3) 0.7333(2) 0.7749(3) 0.0580(6) Uani d . 1 C
H15 0.8588 0.6695 0.7340 0.070 Uiso calc R 1 H
C16 0.8640(2) 0.8762(2) 0.7756(2) 0.0488(5) Uani d . 1 C
C17 0.8087(3) 0.9725(2) 0.8354(3) 0.0570(6) Uani d . 1 C
H17 0.8401 1.0693 0.8352 0.068 Uiso calc R 1 H
C18 0.7064(3) 0.9235(2) 0.8953(3) 0.0564(6) Uani d . 1 C
H18 0.6680 0.9880 0.9355 0.068 Uiso calc R 1 H
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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_publ_flag
C6 N1 C5 118.0(2) y
C6 N1 H1N 114.3(17) ?
C5 N1 H1N 114.8(17) ?
O2 N2 O3 122.9(2) y
O2 N2 C16 118.6(2) y
O3 N2 C16 118.5(2) y
C1 O1 C12 111.62(17) ?
O1 C1 C2 111.0(2) ?
O1 C1 H1A 109.4 ?
C2 C1 H1A 109.4 ?
O1 C1 H1B 109.4 ?
C2 C1 H1B 109.4 ?
H1A C1 H1B 108.0 ?
C1 C2 C3 109.5(2) ?
C1 C2 H2A 109.8 ?
C3 C2 H2A 109.8 ?
C1 C2 H2B 109.8 ?
C3 C2 H2B 109.8 ?
H2A C2 H2B 108.2 ?
C2 C3 C4 112.26(19) ?
C2 C3 H3A 109.2 ?
C4 C3 H3A 109.2 ?
C2 C3 H3B 109.2 ?
C4 C3 H3B 109.2 ?
H3A C3 H3B 107.9 ?
C12 C4 C3 110.30(18) ?
C12 C4 C5 108.21(16) ?
C3 C4 C5 114.84(18) ?
C12 C4 H4 107.7 ?
C3 C4 H4 107.7 ?
C5 C4 H4 107.7 ?
N1 C5 C13 110.25(18) ?
N1 C5 C4 106.65(17) ?
C13 C5 C4 112.94(17) ?
N1 C5 H5 109.0 ?
C13 C5 H5 109.0 ?
C4 C5 H5 109.0 ?
N1 C6 C7 120.4(2) ?
N1 C6 C11 120.5(2) ?
C7 C6 C11 119.1(2) ?
C8 C7 C6 120.6(2) ?
C8 C7 H7 119.7 ?
C6 C7 H7 119.7 ?
C7 C8 C9 120.7(2) ?
C7 C8 H8 119.6 ?
C9 C8 H8 119.6 ?
C10 C9 C8 119.1(2) ?
C10 C9 H9 120.5 ?
C8 C9 H9 120.5 ?
C9 C10 C11 121.9(2) ?
C9 C10 H10 119.0 ?
C11 C10 H10 119.0 ?
C10 C11 C6 118.6(2) ?
C10 C11 C12 120.9(2) ?
C6 C11 C12 120.50(19) ?
O1 C12 C11 106.74(16) ?
O1 C12 C4 111.84(17) ?
C11 C12 C4 112.93(17) ?
O1 C12 H12 108.4 ?
C11 C12 H12 108.4 ?
C4 C12 H12 108.4 ?
C18 C13 C14 118.2(2) ?
C18 C13 C5 121.70(19) ?
C14 C13 C5 120.08(19) ?
C15 C14 C13 121.4(2) ?
C15 C14 H14 119.3 ?
C13 C14 H14 119.3 ?
C16 C15 C14 118.5(2) ?
C16 C15 H15 120.8 ?
C14 C15 H15 120.8 ?
C15 C16 C17 121.8(2) ?
C15 C16 N2 119.1(2) ?
C17 C16 N2 119.1(2) ?
C18 C17 C16 118.8(2) ?
C18 C17 H17 120.6 ?
C16 C17 H17 120.6 ?
C17 C18 C13 121.3(2) ?
C17 C18 H18 119.3 ?
C13 C18 H18 119.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C6 1.385(3) y
N1 C5 1.457(3) y
N1 H1N 0.84(3) ?
N2 O2 1.214(3) y
N2 O3 1.217(3) y
N2 C16 1.466(3) y
O1 C1 1.429(3) ?
O1 C12 1.429(2) ?
C1 C2 1.505(4) ?
C1 H1A 0.9700 ?
C1 H1B 0.9700 ?
C2 C3 1.511(4) ?
C2 H2A 0.9700 ?
C2 H2B 0.9700 ?
C3 C4 1.526(3) ?
C3 H3A 0.9700 ?
C3 H3B 0.9700 ?
C4 C12 1.525(3) ?
C4 C5 1.538(3) ?
C4 H4 0.9800 ?
C5 C13 1.506(3) ?
C5 H5 0.9800 ?
C6 C7 1.393(3) ?
C6 C11 1.396(3) ?
C7 C8 1.368(4) ?
C7 H7 0.9300 ?
C8 C9 1.375(4) ?
C8 H8 0.9300 ?
C9 C10 1.367(3) ?
C9 H9 0.9300 ?
C10 C11 1.389(3) ?
C10 H10 0.9300 ?
C11 C12 1.501(3) ?
C12 H12 0.9800 ?
C13 C18 1.382(3) ?
C13 C14 1.387(3) ?
C14 C15 1.375(3) ?
C14 H14 0.9300 ?
C15 C16 1.370(3) ?
C15 H15 0.9300 ?
C16 C17 1.374(3) ?
C17 C18 1.369(3) ?
C17 H17 0.9300 ?
C18 H18 0.9300 ?
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
N1 H1N O3 2_777 0.84(3) 2.38(3) 3.200(3) 165(2)
C1 H1B O3 1_445 0.97 2.59 3.535(3) 166
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
C12 O1 C1 C2 63.0(3)
O1 C1 C2 C3 -58.1(3)
C1 C2 C3 C4 51.7(3)
C2 C3 C4 C12 -48.7(3)
C2 C3 C4 C5 73.9(3)
C6 N1 C5 C13 176.45(19)
C6 N1 C5 C4 53.5(3)
C12 C4 C5 N1 -64.0(2)
C3 C4 C5 N1 172.33(18)
C12 C4 C5 C13 174.78(17)
C3 C4 C5 C13 51.1(3)
C5 N1 C6 C7 160.0(2)
C5 N1 C6 C11 -22.2(3)
N1 C6 C7 C8 179.1(2)
C11 C6 C7 C8 1.3(4)
C6 C7 C8 C9 -0.9(4)
C7 C8 C9 C10 -0.3(4)
C8 C9 C10 C11 1.1(4)
C9 C10 C11 C6 -0.7(3)
C9 C10 C11 C12 179.7(2)
N1 C6 C11 C10 -178.3(2)
C7 C6 C11 C10 -0.5(3)
N1 C6 C11 C12 1.3(3)
C7 C6 C11 C12 179.1(2)
C1 O1 C12 C11 176.27(19)
C1 O1 C12 C4 -59.8(2)
C10 C11 C12 O1 -72.1(2)
C6 C11 C12 O1 108.3(2)
C10 C11 C12 C4 164.56(19)
C6 C11 C12 C4 -15.0(3)
C3 C4 C12 O1 51.9(2)
C5 C4 C12 O1 -74.5(2)
C3 C4 C12 C11 172.32(17)
C5 C4 C12 C11 45.9(2)
N1 C5 C13 C18 -50.0(3)
C4 C5 C13 C18 69.1(3)
N1 C5 C13 C14 131.9(2)
C4 C5 C13 C14 -108.9(2)
C18 C13 C14 C15 -0.2(3)
C5 C13 C14 C15 177.9(2)
C13 C14 C15 C16 0.2(4)
C14 C15 C16 C17 0.0(4)
C14 C15 C16 N2 179.0(2)
O2 N2 C16 C15 -4.2(3)
O3 N2 C16 C15 176.5(2)
O2 N2 C16 C17 174.8(2)
O3 N2 C16 C17 -4.5(3)
C15 C16 C17 C18 -0.2(3)
N2 C16 C17 C18 -179.2(2)
C16 C17 C18 C13 0.3(3)
C14 C13 C18 C17 -0.1(3)
C5 C13 C18 C17 -178.2(2)
