#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:47:55 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180316 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/30/7153046.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_7153046
loop_
_publ_author_name
'Nakhi, Ali'
'Rahman, Md Shafiqur'
'Seerapu, Guru Pavan Kumar'
'Banote, Rakesh Kumar'
'Kumar, Kummari Lalith'
'Kulkarni, Pushkar'
'Haldar, Devyani'
'Pal, Manojit'
_publ_section_title
;
 Transition metal free hydrolysis/cyclization strategy in a single pot:
 synthesis of fused furo N-heterocycles of pharmacological interest.
;
_journal_issue                   30
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4930
_journal_page_last               4934
_journal_paper_doi               10.1039/c3ob41069b
_journal_volume                  11
_journal_year                    2013
_chemical_formula_sum            'C16 H9 N2 O'
_chemical_formula_weight         245.25
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 120.647(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.558(3)
_cell_length_b                   4.5239(5)
_cell_length_c                   23.971(3)
_cell_measurement_temperature    298(2)
_cell_volume                     2384.4(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9084
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9827
_exptl_absorpt_correction_T_min  0.9776
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0919P)²+0.5844P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1561
_reflns_number_gt                1612
_reflns_number_total             2122
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob41069b.txt
_cod_data_source_block           mono
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7153046
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
O1 O 0.16522(6) 0.2432(3) 0.03087(7) 0.0531(4) Uani 1 1 d .
N1 N 0.18098(7) -0.0775(4) 0.11409(8) 0.0526(5) Uani 1 1 d .
C8 C 0.14724(9) 0.1037(4) 0.06860(10) 0.0455(5) Uani 1 1 d .
C5 C 0.09227(9) -0.1076(4) 0.12750(9) 0.0466(5) Uani 1 1 d .
N2 N 0.05880(7) 0.0886(4) 0.07831(8) 0.0500(5) Uani 1 1 d .
C7 C 0.08665(8) 0.1921(4) 0.04931(9) 0.0451(5) Uani 1 1 d .
C4 C 0.06684(10) -0.2341(4) 0.16179(10) 0.0551(6) Uani 1 1 d .
H4 H 0.0272 -0.1856 0.1502 0.066 Uiso 1 1 calc R
C3 C 0.09871(11) -0.4254(5) 0.21137(11) 0.0602(6) Uani 1 1 d .
H3 H 0.0811 -0.5048 0.2337 0.072 Uiso 1 1 calc R
C10 C 0.11648(9) 0.4178(4) -0.01233(10) 0.0483(5) Uani 1 1 d .
C11 C 0.12509(9) 0.5866(4) -0.05866(9) 0.0476(5) Uani 1 1 d .
C6 C 0.15271(9) -0.1904(4) 0.14539(10) 0.0467(5) Uani 1 1 d .
C16 C 0.18043(10) 0.5817(5) -0.05688(11) 0.0598(6) Uani 1 1 d .
C9 C 0.06949(9) 0.3935(4) -0.00240(10) 0.0490(5) Uani 1 1 d .
H9 H 0.0324 0.4912 -0.0253 0.059 Uiso 1 1 calc R
C12 C 0.07764(10) 0.7537(5) -0.10528(11) 0.0620(6) Uani 1 1 d .
H12 H 0.0406 0.7573 -0.1067 0.074 Uiso 1 1 calc R
C13 C 0.08489(12) 0.9145(5) -0.14946(12) 0.0713(7) Uani 1 1 d .
H13 H 0.0526 1.0249 -0.1809 0.086 Uiso 1 1 calc R
C14 C 0.13957(12) 0.9136(5) -0.14758(12) 0.0693(7) Uani 1 1 d .
H14 H 0.1446 1.0248 -0.1772 0.083 Uiso 1 1 calc R
C1 C 0.18418(9) -0.3908(5) 0.19668(11) 0.0575(6) Uani 1 1 d .
H1 H 0.2235 -0.4469 0.2086 0.069 Uiso 1 1 calc R
C2 C 0.15816(10) -0.5032(5) 0.22886(11) 0.0626(6) Uani 1 1 d .
H2 H 0.1799 -0.6337 0.2630 0.075 Uiso 1 1 calc R
C15 C 0.18633(11) 0.7481(6) -0.10189(12) 0.0706(7) Uani 1 1 d .
H15 H 0.2232 0.7467 -0.1009 0.085 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 0.0016 '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
C8 O1 C10 106.31(14)
C8 N1 C6 112.82(17)
N1 C8 O1 123.58(17)
N1 C8 C7 126.99(19)
O1 C8 C7 109.43(16)
N2 C5 C4 119.68(18)
N2 C5 C6 122.26(18)
C4 C5 C6 118.07(18)
C7 N2 C5 114.71(16)
N2 C7 C9 133.26(18)
N2 C7 C8 121.41(18)
C9 C7 C8 105.32(17)
C3 C4 C5 121.5(2)
C4 C3 C2 119.9(2)
C9 C10 O1 111.36(18)
C9 C10 C11 132.51(19)
O1 C10 C11 116.13(17)
C12 C11 C16 119.5(2)
C12 C11 C10 119.52(18)
C16 C11 C10 120.97(19)
N1 C6 C1 119.38(18)
N1 C6 C5 121.81(18)
C1 C6 C5 118.81(18)
C15 C16 C11 118.6(2)
C10 C9 C7 107.58(17)
C13 C12 C11 120.4(2)
C12 C13 C14 120.5(2)
C15 C14 C13 119.2(2)
C2 C1 C6 120.97(19)
C1 C2 C3 120.7(2)
C14 C15 C16 121.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.360(2)
O1 C10 1.390(2)
N1 C8 1.283(2)
N1 C6 1.378(2)
C8 C7 1.429(3)
C5 N2 1.372(2)
C5 C4 1.404(3)
C5 C6 1.426(3)
N2 C7 1.309(2)
C7 C9 1.416(3)
C4 C3 1.356(3)
C3 C2 1.399(3)
C10 C9 1.343(3)
C10 C11 1.454(3)
C11 C12 1.382(3)
C11 C16 1.393(3)
C6 C1 1.404(3)
C16 C15 1.385(3)
C12 C13 1.373(3)
C13 C14 1.375(3)
C14 C15 1.362(3)
C1 C2 1.349(3)
