#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/57/2205793.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_2205793
loop_
_publ_author_name
'K. Ravikumar'
'B. Sridhar'
'M. Mahesh'
'V. V. Narayana Reddy'
_publ_section_title
;
 4-(4-Nitrophenyl)-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1419
_journal_page_last               o1421
_journal_paper_doi               10.1107/S160053680501175X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C17 H16 N2 O3'
_chemical_formula_moiety         'C17 H16 N2 O3'
_chemical_formula_sum            'C17 H16 N2 O3'
_chemical_formula_weight         296.32
_chemical_name_systematic
;
4-(4-nitrophenyl)-2,3,3a,4,5,9b-hexahydro furo[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                103.411(2)
_cell_angle_beta                 102.791(2)
_cell_angle_gamma                107.081(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1090(10)
_cell_length_b                   9.2626(10)
_cell_length_c                   9.7553(11)
_cell_measurement_reflns_used    2986
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.77
_cell_measurement_theta_min      2.43
_cell_volume                     727.28(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
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'ω scans'
_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  0.0169
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8354
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.98
_diffrn_reflns_theta_min         2.26
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0819P)²+0.1431P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1514
_refine_ls_wR_factor_ref         0.1633
_reflns_number_gt                2549
_reflns_number_total             3308
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz6066.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2205793
_cod_database_fobs_code          2205793
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
O1 0.79382(18) 0.13712(16) 1.02054(14) 0.0749(4) Uani d . 1 O
O2 -0.04776(18) 0.2998(2) 0.43917(18) 0.0861(5) Uani d . 1 O
O3 -0.0843(2) 0.3557(2) 0.6527(2) 0.0902(5) Uani d . 1 O
N1 0.4235(2) -0.10150(18) 0.69462(19) 0.0649(4) Uani d . 1 N
H1N 0.325(3) -0.156(3) 0.669(2) 0.076(6) Uiso d . 1 H
N2 -0.01463(18) 0.30655(18) 0.56938(19) 0.0636(4) Uani d . 1 N
C1 0.7428(3) -0.3391(3) 0.7726(2) 0.0715(5) Uani d . 1 C
H1 0.8144 -0.3920 0.7871 0.086 Uiso calc R 1 H
C2 0.7970(2) -0.1759(2) 0.82518(19) 0.0610(4) Uani d . 1 C
H2 0.9062 -0.1187 0.8756 0.073 Uiso calc R 1 H
C3 0.6920(2) -0.0941(2) 0.80481(17) 0.0526(4) Uani d . 1 C
C4 0.7526(2) 0.0834(2) 0.8606(2) 0.0589(4) Uani d . 1 C
H4 0.8500 0.1255 0.8332 0.071 Uiso calc R 1 H
C5 0.8002(3) 0.2959(3) 1.0618(3) 0.0904(7) Uani d . 1 C
H5A 0.9110 0.3690 1.0903 0.108 Uiso calc R 1 H
H5B 0.7603 0.3165 1.1458 0.108 Uiso calc R 1 H
C6 0.6990(3) 0.3204(2) 0.9338(3) 0.0807(6) Uani d . 1 C
H6A 0.7632 0.4050 0.9050 0.097 Uiso calc R 1 H
H6B 0.6109 0.3477 0.9582 0.097 Uiso calc R 1 H
C7 0.6340(2) 0.1611(2) 0.80886(19) 0.0570(4) Uani d . 1 C
H7 0.6399 0.1787 0.7146 0.068 Uiso calc R 1 H
C8 0.4617(2) 0.0576(2) 0.79315(18) 0.0535(4) Uani d . 1 C
H8 0.4572 0.0505 0.8909 0.064 Uiso calc R 1 H
C9 0.5283(2) -0.1806(2) 0.72604(18) 0.0558(4) Uani d . 1 C
C10 0.4746(3) -0.3465(2) 0.6739(2) 0.0718(5) Uani d . 1 C
H10 0.3659 -0.4051 0.6225 0.086 Uiso calc R 1 H
C11 0.5801(3) -0.4241(2) 0.6976(2) 0.0771(6) Uani d . 1 C
H11 0.5422 -0.5349 0.6630 0.093 Uiso calc R 1 H
C12 0.3386(2) 0.12581(19) 0.73454(17) 0.0514(4) Uani d . 1 C
C13 0.2921(2) 0.1153(2) 0.58588(18) 0.0600(4) Uani d . 1 C
H13 0.3383 0.0667 0.5220 0.072 Uiso calc R 1 H
C14 0.1780(2) 0.1761(2) 0.53161(19) 0.0599(4) Uani d . 1 C
H14 0.1466 0.1682 0.4319 0.072 Uiso calc R 1 H
C15 0.11203(19) 0.24836(18) 0.62823(18) 0.0522(4) Uani d . 1 C
C16 0.1573(2) 0.2634(2) 0.77661(19) 0.0600(4) Uani d . 1 C
H16 0.1125 0.3143 0.8404 0.072 Uiso calc R 1 H
C17 0.2705(2) 0.2015(2) 0.82872(18) 0.0612(5) Uani d . 1 C
H17 0.3018 0.2105 0.9287 0.073 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
C5 O1 C4 106.44(15) ?
C9 N1 C8 118.39(14) y
C9 N1 H1N 115.8(15) ?
C8 N1 H1N 111.9(15) ?
O2 N2 O3 123.25(17) y
O2 N2 C15 118.52(16) y
O3 N2 C15 118.21(16) y
C2 C1 C11 119.19(18) ?
C2 C1 H1 120.4 ?
C11 C1 H1 120.4 ?
C1 C2 C3 121.43(18) ?
C1 C2 H2 119.3 ?
C3 C2 H2 119.3 ?
C2 C3 C9 119.10(16) ?
C2 C3 C4 120.96(16) ?
C9 C3 C4 119.90(15) ?
O1 C4 C3 109.45(14) ?
O1 C4 C7 104.28(14) ?
C3 C4 C7 116.38(14) ?
O1 C4 H4 108.8 ?
C3 C4 H4 108.8 ?
C7 C4 H4 108.8 ?
O1 C5 C6 108.76(18) ?
O1 C5 H5A 109.9 ?
C6 C5 H5A 109.9 ?
O1 C5 H5B 109.9 ?
C6 C5 H5B 109.9 ?
H5A C5 H5B 108.3 ?
C5 C6 C7 105.25(17) ?
C5 C6 H6A 110.7 ?
C7 C6 H6A 110.7 ?
C5 C6 H6B 110.7 ?
C7 C6 H6B 110.7 ?
H6A C6 H6B 108.8 ?
C4 C7 C6 101.77(14) ?
C4 C7 C8 110.36(13) ?
C6 C7 C8 112.98(17) ?
C4 C7 H7 110.5 ?
C6 C7 H7 110.5 ?
C8 C7 H7 110.5 ?
N1 C8 C12 109.96(13) ?
N1 C8 C7 108.79(14) ?
C12 C8 C7 112.23(13) ?
N1 C8 H8 108.6 ?
C12 C8 H8 108.6 ?
C7 C8 H8 108.6 ?
N1 C9 C10 120.81(16) ?
N1 C9 C3 120.22(15) ?
C10 C9 C3 118.90(17) ?
C11 C10 C9 120.79(19) ?
C11 C10 H10 119.6 ?
C9 C10 H10 119.6 ?
C10 C11 C1 120.57(19) ?
C10 C11 H11 119.7 ?
C1 C11 H11 119.7 ?
C17 C12 C13 118.65(15) ?
C17 C12 C8 120.56(14) ?
C13 C12 C8 120.79(15) ?
C14 C13 C12 120.87(16) ?
C14 C13 H13 119.6 ?
C12 C13 H13 119.6 ?
C15 C14 C13 118.62(15) ?
C15 C14 H14 120.7 ?
C13 C14 H14 120.7 ?
C14 C15 C16 122.07(16) ?
C14 C15 N2 118.65(15) ?
C16 C15 N2 119.26(16) ?
C15 C16 C17 118.58(16) ?
C15 C16 H16 120.7 ?
C17 C16 H16 120.7 ?
C16 C17 C12 121.19(15) ?
C16 C17 H17 119.4 ?
C12 C17 H17 119.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C5 1.412(3) ?
O1 C4 1.447(2) ?
O2 N2 1.221(2) y
O3 N2 1.224(2) y
N1 C9 1.389(2) y
N1 C8 1.453(2) y
N1 H1N 0.84(2) ?
N2 C15 1.472(2) y
C1 C2 1.371(3) ?
C1 C11 1.385(3) ?
C1 H1 0.9300 ?
C2 C3 1.393(2) ?
C2 H2 0.9300 ?
C3 C9 1.400(2) ?
C3 C4 1.491(2) ?
C4 C7 1.524(2) ?
C4 H4 0.9800 ?
C5 C6 1.484(3) ?
C5 H5A 0.9700 ?
C5 H5B 0.9700 ?
C6 C7 1.532(3) ?
C6 H6A 0.9700 ?
C6 H6B 0.9700 ?
C7 C8 1.532(2) ?
C7 H7 0.9800 ?
C8 C12 1.511(2) ?
C8 H8 0.9800 ?
C9 C10 1.394(2) ?
C10 C11 1.371(3) ?
C10 H10 0.9300 ?
C11 H11 0.9300 ?
C12 C17 1.389(2) ?
C12 C13 1.389(2) ?
C13 C14 1.385(2) ?
C13 H13 0.9300 ?
C14 C15 1.375(2) ?
C14 H14 0.9300 ?
C15 C16 1.376(2) ?
C16 C17 1.379(2) ?
C16 H16 0.9300 ?
C17 H17 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 O2 2_556 0.84(2) 2.34(2) 3.164(2) 171(2)
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
C11 C1 C2 C3 0.0(3)
C1 C2 C3 C9 -1.4(3)
C1 C2 C3 C4 -179.12(16)
C5 O1 C4 C3 -161.85(17)
C5 O1 C4 C7 -36.7(2)
C2 C3 C4 O1 -72.65(19)
C9 C3 C4 O1 109.66(17)
C2 C3 C4 C7 169.49(15)
C9 C3 C4 C7 -8.2(2)
C4 O1 C5 C6 23.9(3)
O1 C5 C6 C7 -1.5(3)
O1 C4 C7 C6 34.17(18)
C3 C4 C7 C6 154.83(16)
O1 C4 C7 C8 -86.02(16)
C3 C4 C7 C8 34.6(2)
C5 C6 C7 C4 -19.9(2)
C5 C6 C7 C8 98.5(2)
C9 N1 C8 C12 176.64(15)
C9 N1 C8 C7 53.4(2)
C4 C7 C8 N1 -55.20(18)
C6 C7 C8 N1 -168.39(14)
C4 C7 C8 C12 -177.11(14)
C6 C7 C8 C12 69.70(19)
C8 N1 C9 C10 156.30(17)
C8 N1 C9 C3 -26.8(2)
C2 C3 C9 N1 -175.18(15)
C4 C3 C9 N1 2.5(3)
C2 C3 C9 C10 1.8(3)
C4 C3 C9 C10 179.50(16)
N1 C9 C10 C11 176.17(19)
C3 C9 C10 C11 -0.8(3)
C9 C10 C11 C1 -0.7(3)
C2 C1 C11 C10 1.0(3)
N1 C8 C12 C17 134.16(17)
C7 C8 C12 C17 -104.61(18)
N1 C8 C12 C13 -46.3(2)
C7 C8 C12 C13 74.9(2)
C17 C12 C13 C14 -1.2(3)
C8 C12 C13 C14 179.25(16)
C12 C13 C14 C15 0.4(3)
C13 C14 C15 C16 0.7(3)
C13 C14 C15 N2 -177.27(15)
O2 N2 C15 C14 -5.6(2)
O3 N2 C15 C14 172.60(17)
O2 N2 C15 C16 176.31(16)
O3 N2 C15 C16 -5.5(2)
C14 C15 C16 C17 -1.1(3)
N2 C15 C16 C17 176.92(15)
C15 C16 C17 C12 0.2(3)
C13 C12 C17 C16 0.9(3)
C8 C12 C17 C16 -179.59(16)
