#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:51:55 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180158 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/54/7105419.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_7105419
loop_
_publ_author_name
'Selvakumar, Kodirajan'
'Vaithiyanathan, Vadivel'
'Shanmugam, Ponnusamy'
_publ_section_title
;
 An efficient stereoselective synthesis of 3-spirocyclopentene- and
 3-spiropyrazole-2-oxindoles via 1,3-dipolar cycloaddition reaction.
;
_journal_issue                   16
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2826
_journal_page_last               2828
_journal_paper_doi               10.1039/b924066g
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C16 H13 N2 O3'
_chemical_formula_weight         281.28
_chemical_name_systematic
;
?
;
_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                 97.935(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4197(7)
_cell_length_b                   8.7349(5)
_cell_length_c                   14.6663(8)
_cell_measurement_reflns_used    3509
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.72
_cell_volume                     1448.96(15)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_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  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17470
_diffrn_reflns_theta_full        29.35
_diffrn_reflns_theta_max         29.35
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9821
_exptl_absorpt_correction_T_min  0.8921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0564
_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)+(0.0925P)²+0.2901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1577
_refine_ls_wR_factor_ref         0.1792
_reflns_number_gt                2686
_reflns_number_total             3976
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b924066g.txt
_cod_data_source_block           shelxl02
_cod_original_cell_volume        1448.95(14)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7105419
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.81316(15) 0.3301(2) 0.78085(12) 0.0405(4) Uani 1 1 d . . .
C2 C 0.93971(17) 0.2791(2) 0.81564(14) 0.0555(5) Uani 1 1 d . . .
H2 H 0.9995 0.2533 0.7813 0.067 Uiso 1 1 calc R . .
C3 C 0.94419(17) 0.2809(2) 0.91698(14) 0.0531(5) Uani 1 1 d . . .
H3 H 1.0045 0.2365 0.9575 0.064 Uiso 1 1 calc R . .
C4 C 0.85215(15) 0.3532(2) 0.94332(12) 0.0418(4) Uani 1 1 d . . .
C5 C 0.76786(13) 0.41581(18) 0.86284(11) 0.0353(3) Uani 1 1 d . . .
C7 C 0.63751(14) 0.3781(2) 0.86865(12) 0.0420(4) Uani 1 1 d . . .
N1 N 0.57701(12) 0.51221(18) 0.86759(11) 0.0442(4) Uani 1 1 d . . .
C9 C 0.65158(15) 0.63806(19) 0.86202(11) 0.0400(4) Uani 1 1 d . . .
C10 C 0.6230(2) 0.7921(2) 0.85917(14) 0.0559(5) Uani 1 1 d . . .
H10 H 0.5456 0.8249 0.8595 0.067 Uiso 1 1 calc R . .
C11 C 0.7143(2) 0.8956(2) 0.85576(15) 0.0634(6) Uani 1 1 d . . .
H11 H 0.6977 0.9999 0.8546 0.076 Uiso 1 1 calc R . .
C12 C 0.8289(2) 0.8481(2) 0.85398(15) 0.0590(5) Uani 1 1 d . . .
H12 H 0.8886 0.9200 0.8518 0.071 Uiso 1 1 calc R . .
C13 C 0.85565(17) 0.6923(2) 0.85551(12) 0.0459(4) Uani 1 1 d . . .
H13 H 0.9328 0.6592 0.8540 0.055 Uiso 1 1 calc R . .
C14 C 0.76624(14) 0.58850(18) 0.85933(10) 0.0356(3) Uani 1 1 d . . .
C15 C 0.80046(15) 0.4246(2) 0.69429(12) 0.0428(4) Uani 1 1 d . . .
C16 C 0.6619(3) 0.5482(4) 0.58526(19) 0.0954(10) Uani 1 1 d . . .
H16A H 0.7142 0.6348 0.5913 0.143 Uiso 1 1 calc R . .
H16B H 0.5815 0.5832 0.5795 0.143 Uiso 1 1 calc R . .
H16C H 0.6735 0.4907 0.5315 0.143 Uiso 1 1 calc R . .
C17 C 0.83496(16) 0.3869(2) 1.03580(13) 0.0485(4) Uani 1 1 d . . .
C18 C 0.45083(17) 0.5229(3) 0.87038(18) 0.0677(6) Uani 1 1 d . . .
H18A H 0.4181 0.4218 0.8717 0.102 Uiso 1 1 calc R . .
H18B H 0.4139 0.5760 0.8167 0.102 Uiso 1 1 calc R . .
H18C H 0.4370 0.5778 0.9246 0.102 Uiso 1 1 calc R . .
N2 N 0.82009(17) 0.4176(3) 1.10881(13) 0.0708(6) Uani 1 1 d . . .
O1 O 0.59682(13) 0.25087(16) 0.87354(13) 0.0676(4) Uani 1 1 d . . .
O2 O 0.87978(13) 0.46984(19) 0.65651(11) 0.0642(4) Uani 1 1 d . . .
O3 O 0.68660(12) 0.45182(19) 0.66597(9) 0.0582(4) Uani 1 1 d . . .
H1 H 0.7576(18) 0.239(2) 0.7685(14) 0.050(5) Uiso 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 C1 C2 114.68(15) . . ?
C15 C1 C5 112.50(13) . . ?
C2 C1 C5 106.27(14) . . ?
C15 C1 H1 107.0(11) . . ?
C2 C1 H1 111.8(11) . . ?
C5 C1 H1 104.2(12) . . ?
C3 C2 C1 103.41(15) . . ?
C3 C2 H2 128.3 . . ?
C1 C2 H2 128.3 . . ?
C4 C3 C2 112.20(16) . . ?
C4 C3 H3 123.9 . . ?
C2 C3 H3 123.9 . . ?
C3 C4 C17 126.32(16) . . ?
C3 C4 C5 112.78(15) . . ?
C17 C4 C5 120.59(15) . . ?
C14 C5 C4 112.95(13) . . ?
C14 C5 C7 102.03(12) . . ?
C4 C5 C7 113.22(13) . . ?
C14 C5 C1 117.13(13) . . ?
C4 C5 C1 100.60(12) . . ?
C7 C5 C1 111.44(13) . . ?
O1 C7 N1 126.40(16) . . ?
O1 C7 C5 125.59(16) . . ?
N1 C7 C5 108.01(14) . . ?
C7 N1 C9 111.41(14) . . ?
C7 N1 C18 124.10(17) . . ?
C9 N1 C18 124.48(16) . . ?
C10 C9 C14 121.52(17) . . ?
C10 C9 N1 128.51(17) . . ?
C14 C9 N1 109.97(14) . . ?
C9 C10 C11 117.40(19) . . ?
C9 C10 H10 121.3 . . ?
C11 C10 H10 121.3 . . ?
C12 C11 C10 121.73(19) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 120.0(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 118.89(18) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C9 120.44(16) . . ?
C13 C14 C5 130.98(15) . . ?
C9 C14 C5 108.58(14) . . ?
O2 C15 O3 124.59(18) . . ?
O2 C15 C1 125.66(17) . . ?
O3 C15 C1 109.74(15) . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 C4 178.1(2) . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 O3 C16 115.54(17) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C15 1.504(2) . ?
C1 C2 1.531(2) . ?
C1 C5 1.564(2) . ?
C1 H1 1.02(2) . ?
C2 C3 1.480(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.329(2) . ?
C3 H3 0.9300 . ?
C4 C17 1.428(3) . ?
C4 C5 1.518(2) . ?
C5 C14 1.509(2) . ?
C5 C7 1.538(2) . ?
C7 O1 1.211(2) . ?
C7 N1 1.359(2) . ?
N1 C9 1.400(2) . ?
N1 C18 1.450(2) . ?
C9 C10 1.384(3) . ?
C9 C14 1.385(2) . ?
C10 C11 1.386(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.395(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(2) . ?
C13 H13 0.9300 . ?
C15 O2 1.193(2) . ?
C15 O3 1.331(2) . ?
C16 O3 1.448(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 N2 1.139(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 C1 C2 C3 145.77(17) . . . . ?
C5 C1 C2 C3 20.8(2) . . . . ?
C1 C2 C3 C4 -13.1(2) . . . . ?
C2 C3 C4 C17 -174.12(19) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C14 -112.19(18) . . . . ?
C17 C4 C5 C14 61.8(2) . . . . ?
C3 C4 C5 C7 132.48(18) . . . . ?
C17 C4 C5 C7 -53.5(2) . . . . ?
C3 C4 C5 C1 13.5(2) . . . . ?
C17 C4 C5 C1 -172.54(16) . . . . ?
C15 C1 C5 C14 -24.1(2) . . . . ?
C2 C1 C5 C14 102.22(16) . . . . ?
C15 C1 C5 C4 -146.85(14) . . . . ?
C2 C1 C5 C4 -20.57(18) . . . . ?
C15 C1 C5 C7 92.87(16) . . . . ?
C2 C1 C5 C7 -140.86(15) . . . . ?
C14 C5 C7 O1 -179.42(19) . . . . ?
C4 C5 C7 O1 -57.7(2) . . . . ?
C1 C5 C7 O1 54.8(2) . . . . ?
C14 C5 C7 N1 0.41(17) . . . . ?
C4 C5 C7 N1 122.08(16) . . . . ?
C1 C5 C7 N1 -125.37(15) . . . . ?
O1 C7 N1 C9 179.61(19) . . . . ?
C5 C7 N1 C9 -0.22(19) . . . . ?
O1 C7 N1 C18 -1.3(3) . . . . ?
C5 C7 N1 C18 178.85(17) . . . . ?
C7 N1 C9 C10 179.85(18) . . . . ?
C18 N1 C9 C10 0.8(3) . . . . ?
C7 N1 C9 C14 -0.1(2) . . . . ?
C18 N1 C9 C14 -179.16(17) . . . . ?
C14 C9 C10 C11 -1.5(3) . . . . ?
N1 C9 C10 C11 178.55(17) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C13 C14 C9 -0.3(3) . . . . ?
C12 C13 C14 C5 -179.22(17) . . . . ?
C10 C9 C14 C13 1.2(3) . . . . ?
N1 C9 C14 C13 -178.81(14) . . . . ?
C10 C9 C14 C5 -179.59(16) . . . . ?
N1 C9 C14 C5 0.36(18) . . . . ?
C4 C5 C14 C13 56.7(2) . . . . ?
C7 C5 C14 C13 178.59(17) . . . . ?
C1 C5 C14 C13 -59.5(2) . . . . ?
C4 C5 C14 C9 -122.32(15) . . . . ?
C7 C5 C14 C9 -0.46(16) . . . . ?
C1 C5 C14 C9 121.49(15) . . . . ?
C2 C1 C15 O2 -5.7(3) . . . . ?
C5 C1 C15 O2 115.9(2) . . . . ?
C2 C1 C15 O3 174.87(15) . . . . ?
C5 C1 C15 O3 -63.52(19) . . . . ?
C3 C4 C17 N2 139(7) . . . . ?
C5 C4 C17 N2 -34(7) . . . . ?
O2 C15 O3 C16 -2.3(3) . . . . ?
C1 C15 O3 C16 177.2(2) . . . . ?
