# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_GP24A
_audit_block_doi                 10.5517/cc1321lt
_database_code_depnum_ccdc_archive 'CCDC 1014865'
_audit_update_record             
;
2015-09-09 deposited with the CCDC.
2015-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
(5S,11bR)-5-(hydroxymethyl)-11b-methyl-5,6,11,11b-tetrahydro-1H-indolizino[8,7-b]indol-3(2H)-one
_chemical_name_common            Indozolidinoindolones
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N2 O2'
_chemical_formula_sum            'C16 H18 N2 O2'
_chemical_formula_weight         270.32

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.735(3)
_cell_length_b                   11.144(3)
_cell_length_c                   12.745(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1382.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    11819
_cell_measurement_theta_min      2.428
_cell_measurement_theta_max      27.569

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '/f and /w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11819
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.428
_diffrn_reflns_theta_max         27.569
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3138
_reflns_number_gt                2642
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_max     0.958
_reflns_Friedel_fraction_full    0.996

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SAINT v7.68A (Bruker, 2009)'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0358P)²+0.1214P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
?
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration Unk
_refine_ls_number_reflns         3138
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.030

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0843(3) 0.0511(2) 1.04214(16) 0.0567(6) Uani 1 1 d . . . . .
H1 H -0.0152 0.0182 1.0835 0.068 Uiso 1 1 calc R U . . .
C2 C -0.2173(3) 0.0547(2) 1.0772(2) 0.0697(8) Uani 1 1 d . . . . .
H2 H -0.2385 0.0223 1.1424 0.084 Uiso 1 1 calc R U . . .
C3 C -0.3212(3) 0.1059(2) 1.0169(2) 0.0659(8) Uani 1 1 d . . . . .
H3 H -0.4097 0.1102 1.0442 0.079 Uiso 1 1 calc R U . . .
C4 C -0.2964(2) 0.14960(19) 0.91934(19) 0.0511(6) Uani 1 1 d . . . . .
H4 H -0.3665 0.1821 0.8787 0.061 Uiso 1 1 calc R U . . .
C5 C -0.1622(2) 0.14393(18) 0.88247(16) 0.0395(5) Uani 1 1 d . . . . .
C6 C -0.0543(2) 0.09795(18) 0.94302(15) 0.0412(5) Uani 1 1 d . . . . .
C7 C 0.0679(2) 0.10819(17) 0.88148(14) 0.0360(4) Uani 1 1 d . . . . .
C8 C 0.03049(18) 0.15700(16) 0.78857(14) 0.0334(4) Uani 1 1 d . . . . .
C9 C 0.12215(19) 0.18188(17) 0.69785(15) 0.0352(4) Uani 1 1 d . . . . .
C10 C 0.2927(2) 0.05175(16) 0.80594(16) 0.0383(4) Uani 1 1 d . . . . .
H10 H 0.3909 0.0538 0.8226 0.046 Uiso 1 1 calc R U . . .
C11 C 0.2128(2) 0.07475(18) 0.90642(16) 0.0438(5) Uani 1 1 d . . . . .
H11A H 0.2137 0.0032 0.9497 0.053 Uiso 1 1 calc R U . . .
H11B H 0.2561 0.1391 0.9456 0.053 Uiso 1 1 calc R U . . .
C12 C 0.1406(2) 0.31650(19) 0.67190(18) 0.0497(5) Uani 1 1 d . . . . .
H12A H 0.0789 0.3413 0.6162 0.060 Uiso 1 1 calc R U . . .
H12B H 0.1244 0.3660 0.7333 0.060 Uiso 1 1 calc R U . . .
C13 C 0.2893(3) 0.3243(2) 0.6369(2) 0.0620(7) Uani 1 1 d . . . . .
H13A H 0.2972 0.3120 0.5618 0.074 Uiso 1 1 calc R U . . .
H13B H 0.3285 0.4017 0.6547 0.074 Uiso 1 1 calc R U . . .
C14 C 0.3591(2) 0.22537(18) 0.69630(19) 0.0484(5) Uani 1 1 d . . . . .
C15 C 0.2592(2) -0.07115(16) 0.75953(16) 0.0395(5) Uani 1 1 d . . . . .
H15A H 0.1633 -0.0731 0.7390 0.047 Uiso 1 1 calc R U . . .
H15B H 0.3143 -0.0838 0.6971 0.047 Uiso 1 1 calc R U . . .
C16 C 0.0767(2) 0.1145(2) 0.59965(16) 0.0493(5) Uani 1 1 d . . . . .
H16A H 0.1379 0.1329 0.5428 0.074 Uiso 1 1 calc R U . . .
H16B H -0.0150 0.1383 0.5813 0.074 Uiso 1 1 calc R U . . .
H16C H 0.0786 0.0297 0.6130 0.074 Uiso 1 1 calc R U . . .
N1 N 0.26378(15) 0.14754(13) 0.72998(13) 0.0379(4) Uani 1 1 d . . . . .
N2 N -0.10915(16) 0.17757(15) 0.78722(13) 0.0390(4) Uani 1 1 d . . . . .
O1 O 0.48329(16) 0.21433(15) 0.71203(16) 0.0664(5) Uani 1 1 d . . . . .
O2 O 0.28512(15) -0.16494(12) 0.83205(11) 0.0430(4) Uani 1 1 d . . . . .
H2N H -0.156(2) 0.213(2) 0.7377(18) 0.043(6) Uiso 1 1 d . . . . .
H2O H 0.370(3) -0.193(3) 0.824(2) 0.076(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C2 1.370(4) . ?
C1 C6 1.398(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.392(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.358(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9300 . ?
C5 N2 1.372(3) . ?
C5 C6 1.401(3) . ?
C6 C7 1.430(3) . ?
C7 C8 1.353(3) . ?
C7 C11 1.493(3) . ?
C8 N2 1.379(2) . ?
C8 C9 1.487(3) . ?
C9 N1 1.488(2) . ?
C9 C16 1.525(3) . ?
C9 C12 1.547(3) . ?
C10 N1 1.468(2) . ?
C10 C11 1.520(3) . ?
C10 C15 1.527(3) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.517(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.500(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O1 1.231(3) . ?
C14 N1 1.341(2) . ?
C15 O2 1.418(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N2 H2N 0.87(2) . ?
O2 H2O 0.89(3) . ?

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
C2 C1 C6 118.8(3) . . ?
C2 C1 H1 120.6 . . ?
C6 C1 H1 120.6 . . ?
C1 C2 C3 121.3(2) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 117.5(2) . . ?
C3 C4 H4 121.3 . . ?
C5 C4 H4 121.3 . . ?
N2 C5 C4 129.9(2) . . ?
N2 C5 C6 107.75(17) . . ?
C4 C5 C6 122.4(2) . . ?
C1 C6 C5 118.5(2) . . ?
C1 C6 C7 134.4(2) . . ?
C5 C6 C7 107.03(17) . . ?
C8 C7 C6 106.74(17) . . ?
C8 C7 C11 122.76(18) . . ?
C6 C7 C11 130.50(17) . . ?
C7 C8 N2 110.08(17) . . ?
C7 C8 C9 126.44(17) . . ?
N2 C8 C9 123.44(16) . . ?
C8 C9 N1 107.10(15) . . ?
C8 C9 C16 111.84(16) . . ?
N1 C9 C16 111.59(16) . . ?
C8 C9 C12 114.65(16) . . ?
N1 C9 C12 101.56(15) . . ?
C16 C9 C12 109.64(17) . . ?
N1 C10 C11 109.56(15) . . ?
N1 C10 C15 110.85(16) . . ?
C11 C10 C15 111.62(16) . . ?
N1 C10 H10 108.2 . . ?
C11 C10 H10 108.2 . . ?
C15 C10 H10 108.2 . . ?
C7 C11 C10 110.25(16) . . ?
C7 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C7 C11 H11B 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C13 C12 C9 103.28(18) . . ?
C13 C12 H12A 111.1 . . ?
C9 C12 H12A 111.1 . . ?
C13 C12 H12B 111.1 . . ?
C9 C12 H12B 111.1 . . ?
H12A C12 H12B 109.1 . . ?
C14 C13 C12 103.98(18) . . ?
C14 C13 H13A 111.0 . . ?
C12 C13 H13A 111.0 . . ?
C14 C13 H13B 111.0 . . ?
C12 C13 H13B 111.0 . . ?
H13A C13 H13B 109.0 . . ?
O1 C14 N1 124.3(2) . . ?
O1 C14 C13 126.88(19) . . ?
N1 C14 C13 108.86(18) . . ?
O2 C15 C10 111.77(16) . . ?
O2 C15 H15A 109.3 . . ?
C10 C15 H15A 109.3 . . ?
O2 C15 H15B 109.3 . . ?
C10 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 N1 C10 123.28(17) . . ?
C14 N1 C9 112.77(16) . . ?
C10 N1 C9 123.08(14) . . ?
C5 N2 C8 108.36(17) . . ?
C5 N2 H2N 124.4(14) . . ?
C8 N2 H2N 127.0(14) . . ?
C15 O2 H2O 110.5(17) . . ?

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_audit_block_doi                 10.5517/cc14g2pc
_database_code_depnum_ccdc_archive 'CCDC 1056222'
_audit_update_record             
;
2015-09-09 deposited with the CCDC.
2015-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
(5R,11bS)-5-(hydroxymethyl)-11b-methyl-5,6,11,11b-tetrahydro-1H-indolizino[8,7-b]indol-3(2H)-one
_chemical_name_common            indozolidinoindolones
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N2 O2'
_chemical_formula_sum            'C16 H18 N2 O2'
_chemical_formula_weight         270.32

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.821(8)
_cell_length_b                   11.174(8)
_cell_length_c                   12.954(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1421.5(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    12024
_cell_measurement_theta_min      2.407
_cell_measurement_theta_max      27.387

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '/f and /w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12024
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.407
_diffrn_reflns_theta_max         27.387
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3079
_reflns_number_gt                2375
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_max     0.911
_reflns_Friedel_fraction_full    0.994

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'SAINT v7.68A (Bruker, 2009)'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0484P)²+0.0216P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 835 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   1.7(9)
_chemical_absolute_configuration Unk
_refine_ls_number_reflns         3079
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1024
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5846(4) 0.4488(2) -0.04204(19) 0.0606(8) Uani 1 1 d . . . . .
H1 H 0.5160 0.4813 -0.0829 0.073 Uiso 1 1 calc R U . . .
C2 C 0.7168(4) 0.4456(3) -0.0772(2) 0.0744(10) Uani 1 1 d . . . . .
H2 H 0.7376 0.4776 -0.1416 0.089 Uiso 1 1 calc R U . . .
C3 C 0.8209(4) 0.3942(3) -0.0167(3) 0.0718(9) Uani 1 1 d . . . . .
H3 H 0.9087 0.3898 -0.0435 0.086 Uiso 1 1 calc R U . . .
C4 C 0.7964(3) 0.3504(2) 0.0810(2) 0.0556(7) Uani 1 1 d . . . . .
H4 H 0.8660 0.3184 0.1210 0.067 Uiso 1 1 calc R U . . .
C5 C 0.6622(2) 0.3560(2) 0.11768(19) 0.0426(6) Uani 1 1 d . . . . .
C6 C 0.5542(3) 0.4022(2) 0.05699(18) 0.0438(6) Uani 1 1 d . . . . .
C7 C 0.4317(3) 0.3918(2) 0.11852(17) 0.0389(5) Uani 1 1 d . . . . .
C8 C 0.4695(2) 0.34296(19) 0.21139(17) 0.0358(5) Uani 1 1 d . . . . .
C9 C 0.3779(2) 0.3183(2) 0.30200(17) 0.0381(5) Uani 1 1 d . . . . .
C10 C 0.2074(2) 0.44844(19) 0.19397(19) 0.0422(6) Uani 1 1 d . . . . .
H10 H 0.1100 0.4464 0.1777 0.051 Uiso 1 1 calc R U . . .
C11 C 0.2875(3) 0.4254(2) 0.09353(18) 0.0473(6) Uani 1 1 d . . . . .
H11A H 0.2447 0.3613 0.0549 0.057 Uiso 1 1 calc R U . . .
H11B H 0.2867 0.4969 0.0510 0.057 Uiso 1 1 calc R U . . .
C12 C 0.3593(3) 0.1838(2) 0.3280(2) 0.0534(7) Uani 1 1 d . . . . .
H12A H 0.3755 0.1342 0.2677 0.064 Uiso 1 1 calc R U . . .
H12B H 0.4206 0.1593 0.3828 0.064 Uiso 1 1 calc R U . . .
C13 C 0.2106(3) 0.1756(2) 0.3629(3) 0.0659(8) Uani 1 1 d . . . . .
H13A H 0.1719 0.0983 0.3456 0.079 Uiso 1 1 calc R U . . .
H13B H 0.2026 0.1883 0.4367 0.079 Uiso 1 1 calc R U . . .
C14 C 0.1409(3) 0.2749(2) 0.3035(2) 0.0521(7) Uani 1 1 d . . . . .
C15 C 0.2405(2) 0.57109(18) 0.24046(19) 0.0426(6) Uani 1 1 d . . . . .
H15A H 0.1854 0.5836 0.3017 0.051 Uiso 1 1 calc R U . . .
H15B H 0.3355 0.5731 0.2609 0.051 Uiso 1 1 calc R U . . .
C16 C 0.4234(3) 0.3857(3) 0.40025(19) 0.0544(7) Uani 1 1 d . . . . .
H16A H 0.3625 0.3670 0.4559 0.082 Uiso 1 1 calc R U . . .
H16B H 0.4218 0.4703 0.3875 0.082 Uiso 1 1 calc R U . . .
H16C H 0.5141 0.3616 0.4184 0.082 Uiso 1 1 calc R U . . .
N1 N 0.23622(18) 0.35256(15) 0.27007(15) 0.0412(5) Uani 1 1 d . . . . .
N2 N 0.60911(19) 0.32255(17) 0.21283(15) 0.0415(5) Uani 1 1 d . . . . .
O1 O 0.01676(19) 0.28604(18) 0.28806(19) 0.0722(6) Uani 1 1 d . . . . .
O2 O 0.21485(19) 0.66508(14) 0.16799(13) 0.0473(4) Uani 1 1 d . . . . .
H2N H 0.656(3) 0.288(2) 0.266(2) 0.049(7) Uiso 1 1 d . . . . .
H1O H 0.134(3) 0.692(3) 0.174(2) 0.067(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C2 1.376(5) . ?
C1 C6 1.417(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.411(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.402(4) . ?
C4 H4 0.9300 . ?
C5 N2 1.390(3) . ?
C5 C6 1.418(4) . ?
C6 C7 1.447(4) . ?
C7 C8 1.372(3) . ?
C7 C11 1.500(4) . ?
C8 N2 1.390(3) . ?
C8 C9 1.504(3) . ?
C9 N1 1.501(3) . ?
C9 C16 1.545(3) . ?
C9 C12 1.551(4) . ?
C10 N1 1.483(3) . ?
C10 C15 1.532(3) . ?
C10 C11 1.543(4) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.532(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.513(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O1 1.242(3) . ?
C14 N1 1.348(3) . ?
C15 O2 1.431(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N2 H2N 0.92(3) . ?
O2 H1O 0.86(3) . ?

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
C2 C1 C6 119.3(3) . . ?
C2 C1 H1 120.3 . . ?
C6 C1 H1 120.3 . . ?
C1 C2 C3 120.7(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 121.9(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 117.4(3) . . ?
C3 C4 H4 121.3 . . ?
C5 C4 H4 121.3 . . ?
N2 C5 C4 129.9(2) . . ?
N2 C5 C6 108.0(2) . . ?
C4 C5 C6 122.1(2) . . ?
C1 C6 C5 118.5(3) . . ?
C1 C6 C7 134.7(3) . . ?
C5 C6 C7 106.7(2) . . ?
C8 C7 C6 106.8(2) . . ?
C8 C7 C11 123.0(2) . . ?
C6 C7 C11 130.2(2) . . ?
C7 C8 N2 110.1(2) . . ?
C7 C8 C9 126.5(2) . . ?
N2 C8 C9 123.3(2) . . ?
N1 C9 C8 107.03(18) . . ?
N1 C9 C16 111.77(19) . . ?
C8 C9 C16 112.4(2) . . ?
N1 C9 C12 101.40(18) . . ?
C8 C9 C12 114.64(19) . . ?
C16 C9 C12 109.1(2) . . ?
N1 C10 C15 110.14(19) . . ?
N1 C10 C11 110.03(19) . . ?
C15 C10 C11 111.9(2) . . ?
N1 C10 H10 108.2 . . ?
C15 C10 H10 108.2 . . ?
C11 C10 H10 108.2 . . ?
C7 C11 C10 109.97(19) . . ?
C7 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
C7 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C13 C12 C9 103.5(2) . . ?
C13 C12 H12A 111.1 . . ?
C9 C12 H12A 111.1 . . ?
C13 C12 H12B 111.1 . . ?
C9 C12 H12B 111.1 . . ?
H12A C12 H12B 109.0 . . ?
C14 C13 C12 103.7(2) . . ?
C14 C13 H13A 111.0 . . ?
C12 C13 H13A 111.0 . . ?
C14 C13 H13B 111.0 . . ?
C12 C13 H13B 111.0 . . ?
H13A C13 H13B 109.0 . . ?
O1 C14 N1 124.5(2) . . ?
O1 C14 C13 126.8(2) . . ?
N1 C14 C13 108.8(2) . . ?
O2 C15 C10 111.17(19) . . ?
O2 C15 H15A 109.4 . . ?
C10 C15 H15A 109.4 . . ?
O2 C15 H15B 109.4 . . ?
C10 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 N1 C10 123.1(2) . . ?
C14 N1 C9 113.03(19) . . ?
C10 N1 C9 122.98(17) . . ?
C5 N2 C8 108.3(2) . . ?
C5 N2 H2N 126.4(16) . . ?
C8 N2 H2N 125.2(16) . . ?
C15 O2 H1O 111.5(19) . . ?

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
C6 C1 C2 C3 1.3(4) . . . . ?
C1 C2 C3 C4 -2.9(4) . . . . ?
C2 C3 C4 C5 1.5(4) . . . . ?
C3 C4 C5 N2 -177.8(2) . . . . ?
C3 C4 C5 C6 1.4(4) . . . . ?
C2 C1 C6 C5 1.4(4) . . . . ?
C2 C1 C6 C7 179.0(3) . . . . ?
N2 C5 C6 C1 176.5(2) . . . . ?
C4 C5 C6 C1 -2.9(3) . . . . ?
N2 C5 C6 C7 -1.7(2) . . . . ?
C4 C5 C6 C7 178.9(2) . . . . ?
C1 C6 C7 C8 -177.0(3) . . . . ?
C5 C6 C7 C8 0.8(2) . . . . ?
C1 C6 C7 C11 2.8(4) . . . . ?
C5 C6 C7 C11 -179.4(2) . . . . ?
C6 C7 C8 N2 0.5(2) . . . . ?
C11 C7 C8 N2 -179.3(2) . . . . ?
C6 C7 C8 C9 178.1(2) . . . . ?
C11 C7 C8 C9 -1.7(3) . . . . ?
C7 C8 C9 N1 2.3(3) . . . . ?
N2 C8 C9 N1 179.65(19) . . . . ?
C7 C8 C9 C16 -120.8(2) . . . . ?
N2 C8 C9 C16 56.6(3) . . . . ?
C7 C8 C9 C12 113.9(3) . . . . ?
N2 C8 C9 C12 -68.8(3) . . . . ?
C8 C7 C11 C10 23.9(3) . . . . ?
C6 C7 C11 C10 -155.8(2) . . . . ?
N1 C10 C11 C7 -45.3(2) . . . . ?
C15 C10 C11 C7 77.5(2) . . . . ?
N1 C9 C12 C13 -29.0(3) . . . . ?
C8 C9 C12 C13 -143.9(2) . . . . ?
C16 C9 C12 C13 89.1(3) . . . . ?
C9 C12 C13 C14 29.4(3) . . . . ?
C12 C13 C14 O1 162.3(3) . . . . ?
C12 C13 C14 N1 -18.7(3) . . . . ?
N1 C10 C15 O2 179.37(18) . . . . ?
C11 C10 C15 O2 56.7(3) . . . . ?
O1 C14 N1 C10 -12.1(4) . . . . ?
C13 C14 N1 C10 168.8(2) . . . . ?
O1 C14 N1 C9 178.6(3) . . . . ?
C13 C14 N1 C9 -0.5(3) . . . . ?
C15 C10 N1 C14 121.4(2) . . . . ?
C11 C10 N1 C14 -114.8(2) . . . . ?
C15 C10 N1 C9 -70.4(3) . . . . ?
C11 C10 N1 C9 53.4(3) . . . . ?
C8 C9 N1 C14 139.5(2) . . . . ?
C16 C9 N1 C14 -97.1(2) . . . . ?
C12 C9 N1 C14 19.1(3) . . . . ?
C8 C9 N1 C10 -29.8(3) . . . . ?
C16 C9 N1 C10 93.6(3) . . . . ?
C12 C9 N1 C10 -150.3(2) . . . . ?
C4 C5 N2 C8 -178.7(2) . . . . ?
C6 C5 N2 C8 2.0(2) . . . . ?
C7 C8 N2 C5 -1.6(2) . . . . ?
C9 C8 N2 C5 -179.3(2) . . . . ?

_refine_diff_density_max         0.160
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.053

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_spiro_150K
_audit_block_doi                 10.5517/cc14g2sg
_database_code_depnum_ccdc_archive 'CCDC 1056225'
_audit_update_record             
;
2015-08-27 deposited with the CCDC.
2015-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(1'R,7a'S)-7a'-methyl-2',3',7',7a'-tetrahydrospiro[indoline-3,1'-pyrrolizine]-2,5'(6'H)-dione
_chemical_name_common            spiroindolopyrrolizinones
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 N2 O2'
_chemical_formula_sum            'C15 H16 N2 O2'
_chemical_formula_weight         256.30

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   7.289(3)
_cell_length_b                   11.525(4)
_cell_length_c                   14.616(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.587(19)
_cell_angle_gamma                90
_cell_volume                     1227.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8401
_cell_measurement_theta_min      3.302
_cell_measurement_theta_max      27.472

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'XtaLABmini: Fixed Chi 2 circle'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8401
_diffrn_reflns_av_unetI/netI     0.1312
_diffrn_reflns_av_R_equivalents  0.1389
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.302
_diffrn_reflns_theta_max         27.472
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2811
_reflns_number_gt                1189
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     ?
_reflns_Friedel_fraction_full    ?

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     ?
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2811
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2204
_refine_ls_R_factor_gt           0.1267
_refine_ls_wR_factor_ref         0.4145
_refine_ls_wR_factor_gt          0.3225
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
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 . ?

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
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 . . ?

_refine_diff_density_max         1.391
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.114

