#------------------------------------------------------------------------------
#$Date: 2015-12-09 17:24:26 +0200 (Wed, 09 Dec 2015) $
#$Revision: 171298 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/51/7055109.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_7055109
loop_
_publ_author_name
'Bathula, Chandramohan'
'Dangi, Poonam'
'Hati, Santanu'
'Agarwal, Rahul'
'Munshi, Parthapratim'
'Singh, Ashutosh'
'Singh, Shailja'
'Sen, Subhabrata'
_publ_section_title
;
 Diverse synthesis of natural product inspired fused and
 spiro-heterocyclic scaffolds via ring distortion and ring construction
 strategies
;
_journal_issue                   12
_journal_name_full               'New J. Chem.'
_journal_page_first              9281
_journal_paper_doi               10.1039/C5NJ01858G
_journal_volume                  39
_journal_year                    2015
_chemical_formula_moiety         'C15 H16 N2 O2'
_chemical_formula_sum            'C15 H16 N2 O2'
_chemical_formula_weight         256.30
_chemical_name_common            spiroindolopyrrolizinones
_chemical_name_systematic
(1'R,7a'S)-7a'-methyl-2',3',7',7a'-tetrahydrospiro[indoline-3,1'-pyrrolizine]-2,5'(6'H)-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-08-27 deposited with the CCDC.
2015-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.587(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.289(3)
_cell_length_b                   11.525(4)
_cell_length_c                   14.616(5)
_cell_measurement_reflns_used    8401
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.472
_cell_measurement_theta_min      3.302
_cell_volume                     1227.4(8)
_computing_data_collection
'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'XtaLABmini: Fixed Chi 2 circle'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1389
_diffrn_reflns_av_unetI/netI     0.1312
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8401
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.472
_diffrn_reflns_theta_min         3.302
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         1.391
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.114
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2811
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.2204
_refine_ls_R_factor_gt           0.1267
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3225
_refine_ls_wR_factor_ref         0.4145
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1189
_reflns_number_total             2811
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5nj01858g3.cif
_cod_data_source_block           spiro_150K
_cod_depositor_comments
'Adding full bibliography for 7055107--7055109.cif.'
_cod_original_cell_volume        1227.3(8)
_cod_database_code               7055109
_audit_block_doi                 10.5517/cc14g2sg
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.982
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O2 O 0.2039(6) 0.7274(4) 0.7614(3) 0.0530(13) Uani 1 1 d . .
O1 O 0.2755(7) 0.6502(4) 1.0007(3) 0.0619(14) Uani 1 1 d . .
N1 N 0.2302(7) 0.5190(4) 0.8863(3) 0.0391(12) Uani 1 1 d . .
N2 N 0.2625(7) 0.6550(4) 0.6166(3) 0.0451(13) Uani 1 1 d . .
H2N H 0.2985 0.7176 0.5907 0.054 Uiso 1 1 calc R U
C6 C 0.1893(7) 0.4633(5) 0.6336(4) 0.0380(14) Uani 1 1 d . .
C7 C 0.1726(8) 0.5196(5) 0.7255(4) 0.0403(14) Uani 1 1 d . .
C5 C 0.2466(7) 0.5486(5) 0.5720(4) 0.0412(14) Uani 1 1 d . .
C8 C 0.2150(8) 0.6487(6) 0.7054(4) 0.0462(15) Uani 1 1 d . .
C1 C 0.1478(9) 0.3556(5) 0.6027(4) 0.0464(15) Uani 1 1 d . .
H1 H 0.1023 0.2997 0.6419 0.056 Uiso 1 1 calc R U
C15 C 0.3221(9) 0.3443(5) 0.8060(4) 0.0465(15) Uani 1 1 d . .
H15A H 0.3835 0.3201 0.8617 0.070 Uiso 1 1 calc R U
H15B H 0.3889 0.3168 0.7546 0.070 Uiso 1 1 calc R U
H15C H 0.2001 0.3127 0.8034 0.070 Uiso 1 1 calc R U
C9 C 0.3121(8) 0.4754(5) 0.8032(4) 0.0415(15) Uani 1 1 d . .
C11 C -0.0109(9) 0.5093(6) 0.7752(4) 0.0472(16) Uani 1 1 d . .
H11A H -0.0943 0.5701 0.7547 0.057 Uiso 1 1 calc R U
H11B H -0.0677 0.4349 0.7617 0.057 Uiso 1 1 calc R U
C3 C 0.2375(8) 0.4122(6) 0.4514(4) 0.0468(15) Uani 1 1 d . .
H3 H 0.2558 0.3926 0.3906 0.056 Uiso 1 1 calc R U
C2 C 0.1746(8) 0.3299(6) 0.5103(4) 0.0464(16) Uani 1 1 d . .
H2 H 0.1493 0.2555 0.4886 0.056 Uiso 1 1 calc R U
C10 C 0.0284(8) 0.5204(6) 0.8780(4) 0.0498(17) Uani 1 1 d . .
H10A H -0.0207 0.5924 0.9015 0.060 Uiso 1 1 calc R U
H10B H -0.0241 0.4559 0.9110 0.060 Uiso 1 1 calc R U
C13 C 0.5147(9) 0.6051(6) 0.8917(4) 0.0501(16) Uani 1 1 d . .
H13A H 0.6093 0.5787 0.9348 0.060 Uiso 1 1 calc R U
H13B H 0.5408 0.6846 0.8748 0.060 Uiso 1 1 calc R U
C4 C 0.2744(9) 0.5241(6) 0.4808(4) 0.0517(17) Uani 1 1 d . .
H4 H 0.3161 0.5804 0.4409 0.062 Uiso 1 1 calc R U
C14 C 0.3275(9) 0.5967(5) 0.9338(4) 0.0485(16) Uani 1 1 d . .
C12 C 0.5083(8) 0.5279(6) 0.8074(4) 0.0478(16) Uani 1 1 d . .
H12A H 0.5999 0.4671 0.8127 0.057 Uiso 1 1 calc R U
H12B H 0.5306 0.5729 0.7527 0.057 Uiso 1 1 calc R U
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
C14 N1 C9 116.4(5)
C14 N1 C10 123.6(5)
C9 N1 C10 111.5(5)
C8 N2 C5 112.4(5)
C8 N2 H2N 123.8
C5 N2 H2N 123.8
C1 C6 C5 119.7(5)
C1 C6 C7 132.4(5)
C5 C6 C7 107.7(5)
C6 C7 C11 118.8(5)
C6 C7 C8 103.0(4)
C11 C7 C8 110.1(4)
C6 C7 C9 115.8(5)
C11 C7 C9 100.6(4)
C8 C7 C9 108.5(5)
C4 C5 N2 128.2(6)
C4 C5 C6 121.9(6)
N2 C5 C6 109.8(5)
O2 C8 N2 128.6(6)
O2 C8 C7 124.6(5)
N2 C8 C7 106.9(5)
C6 C1 C2 118.8(6)
C6 C1 H1 120.6
C2 C1 H1 120.6
C9 C15 H15A 109.5
C9 C15 H15B 109.5
H15A C15 H15B 109.5
C9 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
N1 C9 C15 110.1(5)
N1 C9 C12 103.3(5)
C15 C9 C12 110.2(5)
N1 C9 C7 102.5(5)
C15 C9 C7 111.7(5)
C12 C9 C7 118.3(5)
C10 C11 C7 108.4(5)
C10 C11 H11A 110.0
C7 C11 H11A 110.0
C10 C11 H11B 110.0
C7 C11 H11B 110.0
H11A C11 H11B 108.4
C2 C3 C4 121.1(5)
C2 C3 H3 119.4
C4 C3 H3 119.4
C3 C2 C1 121.1(6)
C3 C2 H2 119.4
C1 C2 H2 119.4
N1 C10 C11 103.9(4)
N1 C10 H10A 111.0
C11 C10 H10A 111.0
N1 C10 H10B 111.0
C11 C10 H10B 111.0
H10A C10 H10B 109.0
C14 C13 C12 106.5(5)
C14 C13 H13A 110.4
C12 C13 H13A 110.4
C14 C13 H13B 110.4
C12 C13 H13B 110.4
H13A C13 H13B 108.6
C3 C4 C5 117.2(6)
C3 C4 H4 121.4
C5 C4 H4 121.4
O1 C14 N1 125.8(6)
O1 C14 C13 126.4(6)
N1 C14 C13 107.7(5)
C13 C12 C9 105.5(5)
C13 C12 H12A 110.6
C9 C12 H12A 110.6
C13 C12 H12B 110.6
C9 C12 H12B 110.6
H12A C12 H12B 108.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C8 1.226(7)
O1 C14 1.225(7)
N1 C14 1.326(8)
N1 C9 1.457(7)
N1 C10 1.473(8)
N2 C8 1.355(7)
N2 C5 1.391(7)
N2 H2N 0.8600
C6 C1 1.352(8)
C6 C5 1.405(8)
C6 C7 1.500(8)
C7 C11 1.545(7)
C7 C8 1.549(9)
C7 C9 1.588(9)
C5 C4 1.384(8)
C1 C2 1.402(8)
C1 H1 0.9300
C15 C9 1.513(8)
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C9 C12 1.553(8)
C11 C10 1.527(9)
C11 H11A 0.9700
C11 H11B 0.9700
C3 C2 1.368(9)
C3 C4 1.383(9)
C3 H3 0.9300
C2 H2 0.9300
C10 H10A 0.9700
C10 H10B 0.9700
C13 C14 1.515(8)
C13 C12 1.520(9)
C13 H13A 0.9700
C13 H13B 0.9700
C4 H4 0.9300
C12 H12A 0.9700
C12 H12B 0.9700
