# 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 2017

####################################################################### 
# 
# 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_vnat
_database_code_depnum_ccdc_archive 'CCDC 1532099'
_audit_update_record             
;
2017-02-10 deposited with the CCDC.
2017-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1'-Methyldispiro[cyclooctane-1,3'-pyrrolidine-2',2''-indene]-1'',2,3''-trione
_chemical_name_common            ?
_chemical_melting_point          446
_chemical_formula_moiety         'C20 H23 N O3'
_chemical_formula_sum            'C20 H23 N O3'
_chemical_formula_weight         325.39

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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'

_cell_length_a                   7.798(4)
_cell_length_b                   23.059(3)
_cell_length_c                   9.942(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.31(3)
_cell_angle_gamma                90.00
_cell_volume                     1665.4(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      2
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9840
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_process_details   '(North et al., 1968)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  MACH3-Nonius
_diffrn_measurement_method       ω-2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3347
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_sigmaI/netI    0.0565
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2611
_reflns_number_gt                1930
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CAD4 Express (Enraf Nonius, (1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, (1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1996)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-97


_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0618P)²+0.2249P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2611
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0921
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C7 C 0.4290(14) 0.6580(5) 0.1361(12) 0.037(3) Uani 1 1 d . . .
O1 O 0.1506(12) 0.7327(4) -0.1723(9) 0.054(2) Uani 1 1 d . . .
N1 N -0.0455(12) 0.6389(4) -0.0886(11) 0.040(2) Uani 1 1 d . . .
O3 O -0.0904(11) 0.6195(4) -0.4069(10) 0.060(3) Uani 1 1 d . . .
O2 O 0.2487(12) 0.5754(4) 0.1468(9) 0.052(2) Uani 1 1 d . . .
C1 C 0.2247(14) 0.6969(5) -0.0823(12) 0.037(3) Uani 1 1 d . . .
C2 C 0.4014(14) 0.7039(5) 0.0407(12) 0.037(3) Uani 1 1 d . . .
C9 C 0.1481(14) 0.6366(5) -0.0706(12) 0.034(3) Uani 1 1 d . . .
C13 C 0.1510(15) 0.5919(5) -0.1894(12) 0.037(3) Uani 1 1 d . . .
C3 C 0.5252(15) 0.7502(5) 0.0685(14) 0.047(3) Uani 1 1 d . . .
H3 H 0.5054 0.7813 0.0053 0.056 Uiso 1 1 calc R . .
C11 C -0.1244(18) 0.5814(6) -0.1294(16) 0.056(4) Uani 1 1 d . . .
H11A H -0.2424 0.5841 -0.2082 0.067 Uiso 1 1 calc R . .
H11B H -0.1423 0.5627 -0.0481 0.067 Uiso 1 1 calc R . .
C6 C 0.5844(16) 0.6560(5) 0.2618(13) 0.047(3) Uani 1 1 d . . .
H6 H 0.6049 0.6249 0.3252 0.056 Uiso 1 1 calc R . .
C8 C 0.2764(15) 0.6164(5) 0.0814(12) 0.039(3) Uani 1 1 d . . .
C5 C 0.7062(17) 0.7011(7) 0.2896(15) 0.059(4) Uani 1 1 d . . .
H5 H 0.8097 0.7006 0.3741 0.071 Uiso 1 1 calc R . .
C4 C 0.6800(16) 0.7475(6) 0.1955(15) 0.055(4) Uani 1 1 d . . .
H4 H 0.7666 0.7772 0.2172 0.066 Uiso 1 1 calc R . .
C14 C 0.3437(16) 0.5663(5) -0.1590(13) 0.045(3) Uani 1 1 d . . .
H14A H 0.3969 0.5559 -0.0576 0.054 Uiso 1 1 calc R . .
H14B H 0.4209 0.5961 -0.1762 0.054 Uiso 1 1 calc R . .
C16 C 0.266(2) 0.5178(6) -0.4126(15) 0.061(4) Uani 1 1 d . . .
H16A H 0.1347 0.5237 -0.4403 0.073 Uiso 1 1 calc R . .
H16B H 0.2833 0.4810 -0.4534 0.073 Uiso 1 1 calc R . .
C19 C 0.1951(17) 0.6530(5) -0.4013(13) 0.049(3) Uani 1 1 d . . .
H19A H 0.3145 0.6594 -0.3262 0.058 Uiso 1 1 calc R . .
H19B H 0.1422 0.6906 -0.4369 0.058 Uiso 1 1 calc R . .
C20 C 0.0716(15) 0.6218(5) -0.3374(12) 0.038(3) Uani 1 1 d . . .
C17 C 0.341(2) 0.5656(6) -0.4823(16) 0.062(4) Uani 1 1 d . . .
H17A H 0.4611 0.5771 -0.4152 0.074 Uiso 1 1 calc R . .
H17B H 0.3573 0.5498 -0.5674 0.074 Uiso 1 1 calc R . .
C12 C 0.0110(17) 0.5473(5) -0.1757(14) 0.049(3) Uani 1 1 d . . .
H12A H -0.0519 0.5283 -0.2675 0.058 Uiso 1 1 calc R . .
H12B H 0.0724 0.5181 -0.1043 0.058 Uiso 1 1 calc R . .
C18 C 0.2207(19) 0.6186(6) -0.5258(14) 0.056(4) Uani 1 1 d . . .
H18A H 0.1003 0.6068 -0.5921 0.068 Uiso 1 1 calc R . .
H18B H 0.2729 0.6445 -0.5778 0.068 Uiso 1 1 calc R . .
C10 C -0.0909(19) 0.6671(7) 0.0244(16) 0.064(4) Uani 1 1 d . . .
H10A H -0.0486 0.6436 0.1101 0.077 Uiso 1 1 calc R . .
H10B H -0.2219 0.6719 -0.0067 0.077 Uiso 1 1 calc R . .
H10C H -0.0323 0.7044 0.0447 0.077 Uiso 1 1 calc R . .
C15 C 0.3488(19) 0.5126(6) -0.2496(14) 0.054(3) Uani 1 1 d . . .
H15A H 0.4764 0.5010 -0.2233 0.064 Uiso 1 1 calc R . .
H15B H 0.2859 0.4813 -0.2214 0.064 Uiso 1 1 calc R . .


_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
C7 C2 1.385(15) . ?
C7 C6 1.390(15) . ?
C7 C8 1.469(15) . ?
O1 C1 1.200(13) . ?
N1 C10 1.449(15) . ?
N1 C11 1.454(16) . ?
N1 C9 1.455(13) . ?
O3 C20 1.201(13) . ?
O2 C8 1.212(13) . ?
C1 C2 1.482(15) . ?
C1 C9 1.534(15) . ?
C2 C3 1.397(16) . ?
C9 C8 1.550(14) . ?
C9 C13 1.574(15) . ?
C13 C20 1.536(15) . ?
C13 C14 1.539(15) . ?
C13 C12 1.542(15) . ?
C3 C4 1.395(17) . ?
C3 H3 0.9300 . ?
C11 C12 1.516(17) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C6 C5 1.366(18) . ?
C6 H6 0.9300 . ?
C5 C4 1.387(19) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C14 C15 1.540(16) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 C15 1.516(18) . ?
C16 C17 1.525(19) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C19 C20 1.514(16) . ?
C19 C18 1.542(17) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C17 C18 1.506(19) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 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
C2 C7 C6 120.5(11) . . ?
C2 C7 C8 110.0(9) . . ?
C6 C7 C8 129.5(11) . . ?
C10 N1 C11 115.3(10) . . ?
C10 N1 C9 117.1(10) . . ?
C11 N1 C9 108.4(9) . . ?
O1 C1 C2 126.3(11) . . ?
O1 C1 C9 125.7(10) . . ?
C2 C1 C9 107.9(9) . . ?
C7 C2 C3 121.6(11) . . ?
C7 C2 C1 110.3(10) . . ?
C3 C2 C1 128.0(11) . . ?
N1 C9 C1 111.9(9) . . ?
N1 C9 C8 113.8(9) . . ?
C1 C9 C8 102.4(9) . . ?
N1 C9 C13 103.2(9) . . ?
C1 C9 C13 115.1(9) . . ?
C8 C9 C13 110.8(9) . . ?
C20 C13 C14 112.6(10) . . ?
C20 C13 C12 109.4(9) . . ?
C14 C13 C12 113.5(10) . . ?
C20 C13 C9 108.3(9) . . ?
C14 C13 C9 112.5(9) . . ?
C12 C13 C9 99.6(9) . . ?
C4 C3 C2 117.0(12) . . ?
C4 C3 H3 121.5 . . ?
C2 C3 H3 121.5 . . ?
N1 C11 C12 106.7(10) . . ?
N1 C11 H11A 110.4 . . ?
C12 C11 H11A 110.4 . . ?
N1 C11 H11B 110.4 . . ?
C12 C11 H11B 110.4 . . ?
H11A C11 H11B 108.6 . . ?
C5 C6 C7 118.2(12) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
O2 C8 C7 126.1(11) . . ?
O2 C8 C9 125.4(11) . . ?
C7 C8 C9 108.3(9) . . ?
C6 C5 C4 121.9(12) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C4 C3 120.7(12) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C13 C14 C15 115.1(10) . . ?
C13 C14 H14A 108.5 . . ?
C15 C14 H14A 108.5 . . ?
C13 C14 H14B 108.5 . . ?
C15 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C15 C16 C17 117.3(12) . . ?
C15 C16 H16A 108.0 . . ?
C17 C16 H16A 108.0 . . ?
C15 C16 H16B 108.0 . . ?
C17 C16 H16B 108.0 . . ?
H16A C16 H16B 107.2 . . ?
C20 C19 C18 112.4(10) . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
O3 C20 C19 118.4(11) . . ?
O3 C20 C13 120.3(11) . . ?
C19 C20 C13 121.3(9) . . ?
C18 C17 C16 114.6(12) . . ?
C18 C17 H17A 108.6 . . ?
C16 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C11 C12 C13 105.9(10) . . ?
C11 C12 H12A 110.6 . . ?
C13 C12 H12A 110.6 . . ?
C11 C12 H12B 110.6 . . ?
C13 C12 H12B 110.6 . . ?
H12A C12 H12B 108.7 . . ?
C17 C18 C19 115.8(11) . . ?
C17 C18 H18A 108.3 . . ?
C19 C18 H18A 108.3 . . ?
C17 C18 H18B 108.3 . . ?
C19 C18 H18B 108.3 . . ?
H18A C18 H18B 107.4 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C15 C14 118.1(11) . . ?
C16 C15 H15A 107.8 . . ?
C14 C15 H15A 107.8 . . ?
C16 C15 H15B 107.8 . . ?
C14 C15 H15B 107.8 . . ?
H15A C15 H15B 107.1 . . ?

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 C7 C2 C3 -1.4(17) . . . . ?
C8 C7 C2 C3 178.9(10) . . . . ?
C6 C7 C2 C1 -178.5(10) . . . . ?
C8 C7 C2 C1 1.7(13) . . . . ?
O1 C1 C2 C7 169.6(12) . . . . ?
C9 C1 C2 C7 -7.8(13) . . . . ?
O1 C1 C2 C3 -7(2) . . . . ?
C9 C1 C2 C3 175.3(11) . . . . ?
C10 N1 C9 C1 -68.2(13) . . . . ?
C11 N1 C9 C1 159.2(10) . . . . ?
C10 N1 C9 C8 47.3(14) . . . . ?
C11 N1 C9 C8 -85.3(12) . . . . ?
C10 N1 C9 C13 167.4(10) . . . . ?
C11 N1 C9 C13 34.9(12) . . . . ?
O1 C1 C9 N1 -45.1(16) . . . . ?
C2 C1 C9 N1 132.3(10) . . . . ?
O1 C1 C9 C8 -167.4(12) . . . . ?
C2 C1 C9 C8 10.0(11) . . . . ?
O1 C1 C9 C13 72.4(14) . . . . ?
C2 C1 C9 C13 -110.2(10) . . . . ?
N1 C9 C13 C20 74.7(10) . . . . ?
C1 C9 C13 C20 -47.6(12) . . . . ?
C8 C9 C13 C20 -163.1(9) . . . . ?
N1 C9 C13 C14 -160.1(9) . . . . ?
C1 C9 C13 C14 77.6(12) . . . . ?
C8 C9 C13 C14 -37.9(12) . . . . ?
N1 C9 C13 C12 -39.6(10) . . . . ?
C1 C9 C13 C12 -161.8(9) . . . . ?
C8 C9 C13 C12 82.6(10) . . . . ?
C7 C2 C3 C4 1.1(17) . . . . ?
C1 C2 C3 C4 177.7(11) . . . . ?
C10 N1 C11 C12 -148.6(11) . . . . ?
C9 N1 C11 C12 -15.1(13) . . . . ?
C2 C7 C6 C5 1.3(18) . . . . ?
C8 C7 C6 C5 -179.0(12) . . . . ?
C2 C7 C8 O2 -170.9(11) . . . . ?
C6 C7 C8 O2 9(2) . . . . ?
C2 C7 C8 C9 5.0(12) . . . . ?
C6 C7 C8 C9 -174.7(11) . . . . ?
N1 C9 C8 O2 45.8(16) . . . . ?
C1 C9 C8 O2 166.8(11) . . . . ?
C13 C9 C8 O2 -70.0(14) . . . . ?
N1 C9 C8 C7 -130.1(10) . . . . ?
C1 C9 C8 C7 -9.1(11) . . . . ?
C13 C9 C8 C7 114.1(10) . . . . ?
C7 C6 C5 C4 -1(2) . . . . ?
C6 C5 C4 C3 1(2) . . . . ?
C2 C3 C4 C5 -0.9(19) . . . . ?
C20 C13 C14 C15 -70.7(13) . . . . ?
C12 C13 C14 C15 54.3(14) . . . . ?
C9 C13 C14 C15 166.5(10) . . . . ?
C18 C19 C20 O3 -72.1(15) . . . . ?
C18 C19 C20 C13 105.9(12) . . . . ?
C14 C13 C20 O3 144.6(11) . . . . ?
C12 C13 C20 O3 17.4(15) . . . . ?
C9 C13 C20 O3 -90.2(13) . . . . ?
C14 C13 C20 C19 -33.4(14) . . . . ?
C12 C13 C20 C19 -160.6(10) . . . . ?
C9 C13 C20 C19 91.8(12) . . . . ?
C15 C16 C17 C18 -101.3(15) . . . . ?
N1 C11 C12 C13 -11.5(14) . . . . ?
C20 C13 C12 C11 -82.7(12) . . . . ?
C14 C13 C12 C11 150.6(10) . . . . ?
C9 C13 C12 C11 30.7(12) . . . . ?
C16 C17 C18 C19 64.1(16) . . . . ?
C20 C19 C18 C17 -72.6(14) . . . . ?
C17 C16 C15 C14 56.2(17) . . . . ?
C13 C14 C15 C16 56.1(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.118
####################################################################### 
# 
# 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_nm4p2
_database_code_depnum_ccdc_archive 'CCDC 1532101'
_audit_update_record             
;
2017-02-10 deposited with the CCDC.
2017-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'5a,10a-Dihydroxy-3-methyl-2,3,4,5,5a,10a-hexahydro-1,5-methanoindeno [1,2-d] azepine-10,11(1H)-dione'
_chemical_name_common            ?
_chemical_melting_point          446
_chemical_formula_moiety         'C15 H15 N O4'
_chemical_formula_sum            'C15 H15 N O4'
_chemical_formula_weight         273.28

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-p 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5616(7)
_cell_length_b                   8.9033(8)
_cell_length_c                   10.8091(11)
_cell_angle_alpha                72.764(11)
_cell_angle_beta                 80.486(12)
_cell_angle_gamma                72.369(11)
_cell_volume                     660.09(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      2
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9821
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_process_details   '(North et al., 1968)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  MACH3-Nonius
_diffrn_measurement_method       ω-2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2890
_diffrn_reflns_av_R_equivalents  0.0099
_diffrn_reflns_av_sigmaI/netI    0.0108
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         24.97
_reflns_number_total             2316
_reflns_number_gt                2025
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0454P)²+0.1839P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2316
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0927
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.29809(15) 0.41843(13) 0.00498(10) 0.0446(3) Uani 1 1 d . . .
O2 O -0.04087(14) 0.29519(13) 0.08496(10) 0.0421(3) Uani 1 1 d . . .
H2 H -0.1139 0.3846 0.0581 0.063 Uiso 1 1 calc R . .
O3 O -0.02584(16) 0.06248(14) 0.30007(11) 0.0499(3) Uani 1 1 d . . .
H3 H -0.0724 0.0852 0.2313 0.075 Uiso 1 1 calc R . .
N1 N 0.29935(17) 0.38335(15) 0.28995(12) 0.0388(3) Uani 1 1 d . . .
O4 O -0.19177(16) 0.40313(16) 0.45054(11) 0.0538(3) Uani 1 1 d . . .
C8 C 0.2679(2) 0.30815(17) 0.09849(13) 0.0353(3) Uani 1 1 d . . .
C4 C 0.2670(2) 0.26334(19) 0.41090(14) 0.0403(3) Uani 1 1 d . . .
H4A H 0.2445 0.3121 0.4832 0.048 Uiso 1 1 calc R . .
H4B H 0.3768 0.1712 0.4252 0.048 Uiso 1 1 calc R . .
C10 C 0.3067(2) 0.04870(17) 0.24458(14) 0.0372(3) Uani 1 1 d . . .
C7 C 0.07412(19) 0.30768(16) 0.17048(13) 0.0322(3) Uani 1 1 d . . .
C5 C 0.0984(2) 0.20371(18) 0.40485(13) 0.0375(3) Uani 1 1 d . . .
H5 H 0.0730 0.1229 0.4847 0.045 Uiso 1 1 calc R . .
C6 C 0.1144(2) 0.14491(16) 0.28236(13) 0.0348(3) Uani 1 1 d . . .
C9 C 0.3957(2) 0.14516(17) 0.14346(14) 0.0372(3) Uani 1 1 d . . .
C1 C -0.0622(2) 0.35556(19) 0.37706(14) 0.0383(3) Uani 1 1 d . . .
C3 C 0.1375(2) 0.52059(18) 0.25385(15) 0.0406(3) Uani 1 1 d . . .
H3A H 0.1661 0.5959 0.1728 0.049 Uiso 1 1 calc R . .
H3B H 0.0969 0.5788 0.3209 0.049 Uiso 1 1 calc R . .
C2 C -0.0144(2) 0.44610(17) 0.23864(13) 0.0362(3) Uani 1 1 d . . .
H2A H -0.1220 0.5275 0.1970 0.043 Uiso 1 1 calc R . .
C14 C 0.5784(2) 0.0851(2) 0.09741(16) 0.0486(4) Uani 1 1 d . . .
H14 H 0.6375 0.1503 0.0301 0.058 Uiso 1 1 calc R . .
C11 C 0.3986(2) -0.11196(19) 0.30063(17) 0.0496(4) Uani 1 1 d . . .
H11 H 0.3394 -0.1777 0.3674 0.059 Uiso 1 1 calc R . .
C12 C 0.5804(3) -0.1720(2) 0.25488(18) 0.0565(5) Uani 1 1 d . . .
H12 H 0.6442 -0.2794 0.2917 0.068 Uiso 1 1 calc R . .
C13 C 0.6699(2) -0.0751(2) 0.15496(19) 0.0572(5) Uani 1 1 d . . .
H13 H 0.7927 -0.1183 0.1263 0.069 Uiso 1 1 calc R . .
C18 C 0.4702(3) 0.4293(3) 0.2839(2) 0.0624(5) Uani 1 1 d . . .
H18A H 0.4881 0.5036 0.2010 0.094 Uiso 1 1 calc R . .
H18B H 0.5737 0.3334 0.2949 0.094 Uiso 1 1 calc R . .
H18C H 0.4615 0.4811 0.3517 0.094 Uiso 1 1 calc R . .


_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
O1 C8 1.2285(17) . ?
O2 C7 1.4171(16) . ?
O2 H2 0.8200 . ?
O3 C6 1.4219(17) . ?
O3 H3 0.8200 . ?
N1 C3 1.453(2) . ?
N1 C18 1.455(2) . ?
N1 C4 1.4613(19) . ?
O4 C1 1.2088(18) . ?
C8 C9 1.471(2) . ?
C8 C7 1.5419(19) . ?
C4 C5 1.539(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C10 C11 1.386(2) . ?
C10 C9 1.391(2) . ?
C10 C6 1.507(2) . ?
C7 C2 1.5443(19) . ?
C7 C6 1.5720(18) . ?
C5 C1 1.509(2) . ?
C5 C6 1.537(2) . ?
C5 H5 0.9800 . ?
C9 C14 1.387(2) . ?
C1 C2 1.517(2) . ?
C3 C2 1.541(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C2 H2A 0.9800 . ?
C14 C13 1.385(3) . ?
C14 H14 0.9300 . ?
C11 C12 1.381(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
C7 O2 H2 109.5 . . ?
C6 O3 H3 109.5 . . ?
C3 N1 C18 114.32(13) . . ?
C3 N1 C4 113.97(12) . . ?
C18 N1 C4 112.86(13) . . ?
O1 C8 C9 126.53(13) . . ?
O1 C8 C7 124.00(12) . . ?
C9 C8 C7 108.44(12) . . ?
N1 C4 C5 110.50(11) . . ?
N1 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
N1 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C11 C10 C9 120.35(15) . . ?
C11 C10 C6 128.39(14) . . ?
C9 C10 C6 111.20(12) . . ?
O2 C7 C8 108.50(11) . . ?
O2 C7 C2 114.39(11) . . ?
C8 C7 C2 115.40(12) . . ?
O2 C7 C6 108.69(11) . . ?
C8 C7 C6 103.21(11) . . ?
C2 C7 C6 105.84(11) . . ?
C1 C5 C6 100.91(11) . . ?
C1 C5 C4 105.49(12) . . ?
C6 C5 C4 112.08(11) . . ?
C1 C5 H5 112.5 . . ?
C6 C5 H5 112.5 . . ?
C4 C5 H5 112.5 . . ?
O3 C6 C10 114.30(12) . . ?
O3 C6 C5 106.98(11) . . ?
C10 C6 C5 114.94(12) . . ?
O3 C6 C7 111.58(11) . . ?
C10 C6 C7 104.97(11) . . ?
C5 C6 C7 103.62(11) . . ?
C14 C9 C10 121.43(14) . . ?
C14 C9 C8 128.62(14) . . ?
C10 C9 C8 109.95(13) . . ?
O4 C1 C5 128.54(14) . . ?
O4 C1 C2 126.94(14) . . ?
C5 C1 C2 104.23(11) . . ?
N1 C3 C2 105.67(11) . . ?
N1 C3 H3A 110.6 . . ?
C2 C3 H3A 110.6 . . ?
N1 C3 H3B 110.6 . . ?
C2 C3 H3B 110.6 . . ?
H3A C3 H3B 108.7 . . ?
C1 C2 C3 103.05(11) . . ?
C1 C2 C7 103.33(11) . . ?
C3 C2 C7 109.41(11) . . ?
C1 C2 H2A 113.4 . . ?
C3 C2 H2A 113.4 . . ?
C7 C2 H2A 113.4 . . ?
C13 C14 C9 117.82(16) . . ?
C13 C14 H14 121.1 . . ?
C9 C14 H14 121.1 . . ?
C12 C11 C10 118.30(16) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C11 C12 C13 121.32(15) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 120.77(16) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
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 . . ?

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
C3 N1 C4 C5 54.45(16) . . . . ?
C18 N1 C4 C5 -172.98(13) . . . . ?
O1 C8 C7 O2 66.57(17) . . . . ?
C9 C8 C7 O2 -102.49(12) . . . . ?
O1 C8 C7 C2 -63.28(18) . . . . ?
C9 C8 C7 C2 127.66(12) . . . . ?
O1 C8 C7 C6 -178.24(13) . . . . ?
C9 C8 C7 C6 12.70(14) . . . . ?
N1 C4 C5 C1 -56.97(15) . . . . ?
N1 C4 C5 C6 51.96(16) . . . . ?
C11 C10 C6 O3 -48.1(2) . . . . ?
C9 C10 C6 O3 134.84(13) . . . . ?
C11 C10 C6 C5 76.15(19) . . . . ?
C9 C10 C6 C5 -100.88(14) . . . . ?
C11 C10 C6 C7 -170.70(15) . . . . ?
C9 C10 C6 C7 12.27(15) . . . . ?
C1 C5 C6 O3 -80.03(13) . . . . ?
C4 C5 C6 O3 168.14(11) . . . . ?
C1 C5 C6 C10 151.91(12) . . . . ?
C4 C5 C6 C10 40.09(16) . . . . ?
C1 C5 C6 C7 37.97(13) . . . . ?
C4 C5 C6 C7 -73.85(14) . . . . ?
O2 C7 C6 O3 -23.90(15) . . . . ?
C8 C7 C6 O3 -138.96(12) . . . . ?
C2 C7 C6 O3 99.41(13) . . . . ?
O2 C7 C6 C10 100.42(12) . . . . ?
C8 C7 C6 C10 -14.64(14) . . . . ?
C2 C7 C6 C10 -136.28(11) . . . . ?
O2 C7 C6 C5 -138.66(11) . . . . ?
C8 C7 C6 C5 106.28(12) . . . . ?
C2 C7 C6 C5 -15.36(14) . . . . ?
C11 C10 C9 C14 -1.1(2) . . . . ?
C6 C10 C9 C14 176.26(14) . . . . ?
C11 C10 C9 C8 178.38(14) . . . . ?
C6 C10 C9 C8 -4.31(17) . . . . ?
O1 C8 C9 C14 4.9(3) . . . . ?
C7 C8 C9 C14 173.60(15) . . . . ?
O1 C8 C9 C10 -174.49(14) . . . . ?
C7 C8 C9 C10 -5.78(16) . . . . ?
C6 C5 C1 O4 138.05(16) . . . . ?
C4 C5 C1 O4 -105.16(17) . . . . ?
C6 C5 C1 C2 -47.81(13) . . . . ?
C4 C5 C1 C2 68.98(13) . . . . ?
C18 N1 C3 C2 168.31(13) . . . . ?
C4 N1 C3 C2 -59.82(15) . . . . ?
O4 C1 C2 C3 98.33(17) . . . . ?
C5 C1 C2 C3 -75.95(13) . . . . ?
O4 C1 C2 C7 -147.76(15) . . . . ?
C5 C1 C2 C7 37.97(14) . . . . ?
N1 C3 C2 C1 69.03(14) . . . . ?
N1 C3 C2 C7 -40.39(14) . . . . ?
O2 C7 C2 C1 106.41(13) . . . . ?
C8 C7 C2 C1 -126.65(12) . . . . ?
C6 C7 C2 C1 -13.22(14) . . . . ?
O2 C7 C2 C3 -144.35(12) . . . . ?
C8 C7 C2 C3 -17.42(15) . . . . ?
C6 C7 C2 C3 96.02(13) . . . . ?
C10 C9 C14 C13 0.3(2) . . . . ?
C8 C9 C14 C13 -178.97(15) . . . . ?
C9 C10 C11 C12 1.0(2) . . . . ?
C6 C10 C11 C12 -175.81(15) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C9 C14 C13 C12 0.4(3) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.82 1.90 2.7168(15) 175.0 2_565
C2 H2A O1 0.98 2.59 3.3778(18) 137.2 2_565
C18 H18A O1 0.96 2.57 3.432(2) 148.9 2_665
C5 H5 O3 0.98 2.46 3.4381(18) 172.7 2_556
O3 H3 O2 0.82 2.11 2.6080(15) 119.1 .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_ax79m
_database_code_depnum_ccdc_archive 'CCDC 1532100'
_audit_update_record             
;
2017-02-10 deposited with the CCDC.
2017-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
5-Benzyl-7a-hydroxy-1-methyl-2,3,5,6,7,7a-hexahydro-1H-3a,7-methano-indeno[2,1-d]pyrrolo[3,2-c]azepine-12,13(4H)-dione
_chemical_name_common            ?
_chemical_melting_point          165
_chemical_formula_moiety         'C24 H24 N2 O3'
_chemical_formula_sum            'C24 H24 N2 O3'
_chemical_formula_weight         388.45

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_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                   9.2706(9)
_cell_length_b                   19.7818(18)
_cell_length_c                   10.5006(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.5720(10)
_cell_angle_gamma                90
_cell_volume                     1922.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      2
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9840
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_process_details   '(North et al., 1968)'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  MACH3-Nonius
_diffrn_measurement_method       ω-2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20063
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.059
_diffrn_reflns_theta_max         26.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3878
_reflns_number_gt                3524
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0556P)²+0.5188P] 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_number_reflns         3878
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1092
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_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 0.13803(13) 0.61090(6) 0.65257(11) 0.0322(3) Uani 1 1 d . . . . .
C2 C 0.10286(13) 0.65502(6) 0.76683(12) 0.0357(3) Uani 1 1 d . . . . .
C3 C 0.12101(12) 0.61314(6) 0.88283(11) 0.0347(3) Uani 1 1 d . . . . .
C4 C 0.08998(14) 0.62967(8) 1.00729(13) 0.0456(3) Uani 1 1 d . . . . .
H4 H 0.0504 0.6714 1.0260 0.055 Uiso 1 1 calc R U . . .
C5 C 0.11960(16) 0.58243(9) 1.10187(13) 0.0538(4) Uani 1 1 d . . . . .
H5 H 0.0979 0.5920 1.1853 0.065 Uiso 1 1 calc R U . . .
C6 C 0.18131(17) 0.52088(9) 1.07394(13) 0.0521(4) Uani 1 1 d . . . . .
H6 H 0.2026 0.4902 1.1396 0.063 Uiso 1 1 calc R U . . .
C7 C 0.21201(15) 0.50394(7) 0.95059(12) 0.0425(3) Uani 1 1 d . . . . .
H7 H 0.2532 0.4624 0.9326 0.051 Uiso 1 1 calc R U . . .
C8 C 0.17969(13) 0.55062(6) 0.85466(11) 0.0328(3) Uani 1 1 d . . . . .
C9 C 0.19690(13) 0.54241(6) 0.71343(11) 0.0323(3) Uani 1 1 d . . . . .
C10 C 0.35254(14) 0.53664(7) 0.66915(12) 0.0378(3) Uani 1 1 d . . . . .
H10 H 0.3828 0.4894 0.6621 0.045 Uiso 1 1 calc R U . . .
C11 C 0.46576(14) 0.57892(7) 0.74637(13) 0.0415(3) Uani 1 1 d . . . . .
H11A H 0.4839 0.5588 0.8301 0.050 Uiso 1 1 calc R U . . .
H11B H 0.5556 0.5784 0.7038 0.050 Uiso 1 1 calc R U . . .
C12 C 0.37071(15) 0.68036(7) 0.63922(13) 0.0427(3) Uani 1 1 d . . . . .
H12A H 0.4529 0.6861 0.5875 0.051 Uiso 1 1 calc R U . . .
H12B H 0.3307 0.7247 0.6548 0.051 Uiso 1 1 calc R U . . .
C13 C 0.25634(14) 0.63665(6) 0.56720(11) 0.0365(3) Uani 1 1 d . . . . .
C14 C 0.33226(14) 0.57007(7) 0.53975(12) 0.0411(3) Uani 1 1 d . . . . .
C15 C 0.17964(16) 0.66988(8) 0.45070(13) 0.0473(3) Uani 1 1 d . . . . .
H15A H 0.1977 0.7182 0.4504 0.057 Uiso 1 1 calc R U . . .
H15B H 0.2120 0.6505 0.3725 0.057 Uiso 1 1 calc R U . . .
C16 C 0.02049(16) 0.65534(7) 0.46388(13) 0.0461(3) Uani 1 1 d . . . . .
H16A H -0.0286 0.6954 0.4921 0.055 Uiso 1 1 calc R U . . .
H16B H -0.0253 0.6410 0.3828 0.055 Uiso 1 1 calc R U . . .
C17 C -0.12814(15) 0.59651(9) 0.61177(14) 0.0503(4) Uani 1 1 d . . . . .
H17A H -0.1272 0.5613 0.6748 0.075 Uiso 1 1 calc R U . . .
H17B H -0.1997 0.5864 0.5444 0.075 Uiso 1 1 calc R U . . .
H17C H -0.1509 0.6388 0.6505 0.075 Uiso 1 1 calc R U . . .
C18 C 0.53082(16) 0.69127(8) 0.82480(14) 0.0517(4) Uani 1 1 d . . . . .
H18A H 0.4979 0.7378 0.8216 0.062 Uiso 1 1 calc R U . . .
H18B H 0.6166 0.6887 0.7766 0.062 Uiso 1 1 calc R U . . .
C19 C 0.57308(14) 0.67374(7) 0.96199(13) 0.0418(3) Uani 1 1 d . . . . .
C20 C 0.47875(15) 0.64321(7) 1.04175(14) 0.0448(3) Uani 1 1 d . . . . .
H20 H 0.3872 0.6303 1.0092 0.054 Uiso 1 1 calc R U . . .
C21 C 0.51873(16) 0.63160(8) 1.16904(14) 0.0479(3) Uani 1 1 d . . . . .
H21 H 0.4548 0.6104 1.2210 0.057 Uiso 1 1 calc R U . . .
C22 C 0.65352(17) 0.65145(8) 1.21894(15) 0.0504(4) Uani 1 1 d . . . . .
H22 H 0.6802 0.6441 1.3047 0.061 Uiso 1 1 calc R U . . .
C23 C 0.74812(16) 0.68221(8) 1.14123(16) 0.0535(4) Uani 1 1 d . . . . .
H23 H 0.8387 0.6960 1.1747 0.064 Uiso 1 1 calc R U . . .
C24 C 0.70882(15) 0.69269(8) 1.01361(15) 0.0497(3) Uani 1 1 d . . . . .
H24 H 0.7742 0.7127 0.9615 0.060 Uiso 1 1 calc R U . . .
N1 N 0.01427(11) 0.60100(5) 0.55938(10) 0.0369(2) Uani 1 1 d . . . . .
N2 N 0.41852(11) 0.64898(6) 0.76106(10) 0.0383(3) Uani 1 1 d . . . . .
O1 O 0.11642(12) 0.48501(5) 0.66853(9) 0.0458(3) Uani 1 1 d . . . . .
O2 O 0.06088(12) 0.71311(5) 0.75878(10) 0.0524(3) Uani 1 1 d . . . . .
O3 O 0.36618(14) 0.55010(6) 0.43767(10) 0.0644(3) Uani 1 1 d . . . . .
H1O H 0.075(2) 0.4966(11) 0.600(2) 0.082(7) 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 N1 1.4740(15) . ?
C1 C2 1.5350(16) . ?
C1 C13 1.5456(17) . ?
C1 C9 1.5805(16) . ?
C2 O2 1.2145(16) . ?
C2 C3 1.4741(18) . ?
C3 C8 1.3903(18) . ?
C3 C4 1.3945(17) . ?
C4 C5 1.379(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.3855(18) . ?
C7 H7 0.9300 . ?
C8 C9 1.5101(16) . ?
C9 O1 1.4229(15) . ?
C9 C10 1.5475(17) . ?
C10 C14 1.5123(17) . ?
C10 C11 1.5339(19) . ?
C10 H10 0.9800 . ?
C11 N2 1.4646(18) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N2 1.4656(16) . ?
C12 C13 1.5310(19) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C15 1.5251(17) . ?
C13 C14 1.5291(18) . ?
C14 O3 1.2024(16) . ?
C15 C16 1.518(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N1 1.4736(17) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N1 1.4642(18) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 N2 1.4645(17) . ?
C18 C19 1.509(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.386(2) . ?
C19 C24 1.3902(19) . ?
C20 C21 1.384(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.382(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.376(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.382(2) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
O1 H1O 0.83(2) . ?

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
N1 C1 C2 113.58(10) . . ?
N1 C1 C13 102.12(9) . . ?
C2 C1 C13 117.32(10) . . ?
N1 C1 C9 112.92(10) . . ?
C2 C1 C9 104.84(9) . . ?
C13 C1 C9 106.11(9) . . ?
O2 C2 C3 127.51(12) . . ?
O2 C2 C1 124.49(12) . . ?
C3 C2 C1 107.90(10) . . ?
C8 C3 C4 120.95(12) . . ?
C8 C3 C2 110.50(10) . . ?
C4 C3 C2 128.53(12) . . ?
C5 C4 C3 118.20(14) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C4 C5 C6 120.66(13) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 121.53(14) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C8 118.10(14) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
C7 C8 C3 120.53(12) . . ?
C7 C8 C9 127.67(12) . . ?
C3 C8 C9 111.79(10) . . ?
O1 C9 C8 109.02(10) . . ?
O1 C9 C10 108.72(10) . . ?
C8 C9 C10 117.43(10) . . ?
O1 C9 C1 112.91(10) . . ?
C8 C9 C1 104.48(9) . . ?
C10 C9 C1 104.28(9) . . ?
C14 C10 C11 106.21(11) . . ?
C14 C10 C9 99.89(10) . . ?
C11 C10 C9 114.90(10) . . ?
C14 C10 H10 111.7 . . ?
C11 C10 H10 111.7 . . ?
C9 C10 H10 111.7 . . ?
N2 C11 C10 111.86(10) . . ?
N2 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
N2 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N2 C12 C13 110.76(10) . . ?
N2 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C15 C13 C14 114.65(11) . . ?
C15 C13 C12 115.26(11) . . ?
C14 C13 C12 105.48(11) . . ?
C15 C13 C1 107.16(10) . . ?
C14 C13 C1 100.20(10) . . ?
C12 C13 C1 113.22(10) . . ?
O3 C14 C10 129.23(13) . . ?
O3 C14 C13 126.87(12) . . ?
C10 C14 C13 103.90(10) . . ?
C16 C15 C13 104.62(11) . . ?
C16 C15 H15A 110.8 . . ?
C13 C15 H15A 110.8 . . ?
C16 C15 H15B 110.8 . . ?
C13 C15 H15B 110.8 . . ?
H15A C15 H15B 108.9 . . ?
N1 C16 C15 106.25(10) . . ?
N1 C16 H16A 110.5 . . ?
C15 C16 H16A 110.5 . . ?
N1 C16 H16B 110.5 . . ?
C15 C16 H16B 110.5 . . ?
H16A C16 H16B 108.7 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 C19 116.09(11) . . ?
N2 C18 H18A 108.3 . . ?
C19 C18 H18A 108.3 . . ?
N2 C18 H18B 108.3 . . ?
C19 C18 H18B 108.3 . . ?
H18A C18 H18B 107.4 . . ?
C20 C19 C24 118.14(13) . . ?
C20 C19 C18 122.72(12) . . ?
C24 C19 C18 119.01(13) . . ?
C21 C20 C19 120.98(13) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C20 120.04(14) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 119.70(14) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 120.12(14) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C19 121.00(14) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?
C17 N1 C16 111.98(11) . . ?
C17 N1 C1 116.20(10) . . ?
C16 N1 C1 107.04(10) . . ?
C18 N2 C11 112.33(11) . . ?
C18 N2 C12 108.95(10) . . ?
C11 N2 C12 112.65(11) . . ?
C9 O1 H1O 105.9(15) . . ?

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
N1 C1 C2 O2 -59.81(16) . . . . ?
C13 C1 C2 O2 59.08(17) . . . . ?
C9 C1 C2 O2 176.46(12) . . . . ?
N1 C1 C2 C3 116.93(11) . . . . ?
C13 C1 C2 C3 -124.17(11) . . . . ?
C9 C1 C2 C3 -6.79(12) . . . . ?
O2 C2 C3 C8 -176.40(13) . . . . ?
C1 C2 C3 C8 6.98(13) . . . . ?
O2 C2 C3 C4 2.3(2) . . . . ?
C1 C2 C3 C4 -174.28(12) . . . . ?
C8 C3 C4 C5 0.25(19) . . . . ?
C2 C3 C4 C5 -178.37(13) . . . . ?
C3 C4 C5 C6 1.3(2) . . . . ?
C4 C5 C6 C7 -1.6(2) . . . . ?
C5 C6 C7 C8 0.2(2) . . . . ?
C6 C7 C8 C3 1.37(19) . . . . ?
C6 C7 C8 C9 -177.02(12) . . . . ?
C4 C3 C8 C7 -1.63(18) . . . . ?
C2 C3 C8 C7 177.22(11) . . . . ?
C4 C3 C8 C9 176.99(11) . . . . ?
C2 C3 C8 C9 -4.16(14) . . . . ?
C7 C8 C9 O1 57.25(16) . . . . ?
C3 C8 C9 O1 -121.25(11) . . . . ?
C7 C8 C9 C10 -66.90(16) . . . . ?
C3 C8 C9 C10 114.60(12) . . . . ?
C7 C8 C9 C1 178.20(12) . . . . ?
C3 C8 C9 C1 -0.30(13) . . . . ?
N1 C1 C9 O1 -1.48(14) . . . . ?
C2 C1 C9 O1 122.66(10) . . . . ?
C13 C1 C9 O1 -112.54(11) . . . . ?
N1 C1 C9 C8 -119.81(10) . . . . ?
C2 C1 C9 C8 4.33(12) . . . . ?
C13 C1 C9 C8 129.13(10) . . . . ?
N1 C1 C9 C10 116.37(11) . . . . ?
C2 C1 C9 C10 -119.49(10) . . . . ?
C13 C1 C9 C10 5.31(12) . . . . ?
O1 C9 C10 C14 87.72(11) . . . . ?
C8 C9 C10 C14 -147.98(11) . . . . ?
C1 C9 C10 C14 -32.97(12) . . . . ?
O1 C9 C10 C11 -159.12(10) . . . . ?
C8 C9 C10 C11 -34.82(15) . . . . ?
C1 C9 C10 C11 80.19(12) . . . . ?
C14 C10 C11 N2 60.08(13) . . . . ?
C9 C10 C11 N2 -49.31(14) . . . . ?
N2 C12 C13 C15 169.71(11) . . . . ?
N2 C12 C13 C14 -62.75(13) . . . . ?
N2 C12 C13 C1 45.83(15) . . . . ?
N1 C1 C13 C15 25.67(13) . . . . ?
C2 C1 C13 C15 -99.17(13) . . . . ?
C9 C1 C13 C15 144.14(11) . . . . ?
N1 C1 C13 C14 -94.27(10) . . . . ?
C2 C1 C13 C14 140.89(11) . . . . ?
C9 C1 C13 C14 24.19(11) . . . . ?
N1 C1 C13 C12 153.88(10) . . . . ?
C2 C1 C13 C12 29.03(15) . . . . ?
C9 C1 C13 C12 -87.66(12) . . . . ?
C11 C10 C14 O3 110.92(17) . . . . ?
C9 C10 C14 O3 -129.37(16) . . . . ?
C11 C10 C14 C13 -69.37(12) . . . . ?
C9 C10 C14 C13 50.35(12) . . . . ?
C15 C13 C14 O3 18.6(2) . . . . ?
C12 C13 C14 O3 -109.26(16) . . . . ?
C1 C13 C14 O3 133.00(15) . . . . ?
C15 C13 C14 C10 -161.09(11) . . . . ?
C12 C13 C14 C10 71.01(12) . . . . ?
C1 C13 C14 C10 -46.73(12) . . . . ?
C14 C13 C15 C16 103.82(13) . . . . ?
C12 C13 C15 C16 -133.41(13) . . . . ?
C1 C13 C15 C16 -6.40(15) . . . . ?
C13 C15 C16 N1 -15.59(15) . . . . ?
N2 C18 C19 C20 -27.9(2) . . . . ?
N2 C18 C19 C24 156.33(14) . . . . ?
C24 C19 C20 C21 -0.3(2) . . . . ?
C18 C19 C20 C21 -176.11(14) . . . . ?
C19 C20 C21 C22 1.0(2) . . . . ?
C20 C21 C22 C23 -0.6(2) . . . . ?
C21 C22 C23 C24 -0.5(2) . . . . ?
C22 C23 C24 C19 1.2(2) . . . . ?
C20 C19 C24 C23 -0.8(2) . . . . ?
C18 C19 C24 C23 175.14(15) . . . . ?
C15 C16 N1 C17 161.71(12) . . . . ?
C15 C16 N1 C1 33.27(14) . . . . ?
C2 C1 N1 C17 -34.69(15) . . . . ?
C13 C1 N1 C17 -161.98(11) . . . . ?
C9 C1 N1 C17 84.51(13) . . . . ?
C2 C1 N1 C16 91.25(12) . . . . ?
C13 C1 N1 C16 -36.04(12) . . . . ?
C9 C1 N1 C16 -149.54(10) . . . . ?
C19 C18 N2 C11 -65.42(17) . . . . ?
C19 C18 N2 C12 169.04(13) . . . . ?
C10 C11 N2 C18 -174.94(11) . . . . ?
C10 C11 N2 C12 -51.45(14) . . . . ?
C13 C12 N2 C18 178.24(12) . . . . ?
C13 C12 N2 C11 52.89(14) . . . . ?

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_ak58m
_database_code_depnum_ccdc_archive 'CCDC 1532098'
_audit_update_record             
;
2017-02-10 deposited with the CCDC.
2017-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
"6a-Hydroxy-1-methyl-4-phenyl-2,3,6,6a-tetrahydro-1H,4H,11H-3a,6-methanoindeno [2',1':4,5]thiopyrano[4,3-b]pyrrole-11,12-dione"
_chemical_name_common            ?
_chemical_melting_point          446
_chemical_formula_moiety         'C22 H19 N O3 S'
_chemical_formula_sum            'C22 H19 N O3 S'
_chemical_formula_weight         377.44

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab'


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

_cell_length_a                   11.7935(10)
_cell_length_b                   12.3784(10)
_cell_length_c                   24.810(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3621.9(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      2
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1584
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9840
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_process_details   '(North et al., 1968)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  MACH3-Nonius
_diffrn_measurement_method       ω-2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32676
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0101
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3188
_reflns_number_gt                2982
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0531P)²+1.0961P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3188
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0917
_refine_ls_wR_factor_gt          0.0897
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.18788(11) 0.77479(12) -0.05074(5) 0.0353(3) Uani 1 1 d . . .
C2 C 0.15098(13) 0.86428(13) -0.07949(6) 0.0433(4) Uani 1 1 d . . .
H2 H 0.1349 0.9283 -0.0614 0.052 Uiso 1 1 calc R . .
C3 C 0.13791(16) 0.85912(16) -0.13491(7) 0.0559(4) Uani 1 1 d . . .
H3 H 0.1129 0.9195 -0.1538 0.067 Uiso 1 1 calc R . .
C4 C 0.16185(17) 0.76502(17) -0.16218(7) 0.0613(5) Uani 1 1 d . . .
H4 H 0.1531 0.7617 -0.1994 0.074 Uiso 1 1 calc R . .
C5 C 0.19893(15) 0.67555(16) -0.13401(7) 0.0556(4) Uani 1 1 d . . .
H5 H 0.2150 0.6118 -0.1523 0.067 Uiso 1 1 calc R . .
C6 C 0.21234(13) 0.68024(13) -0.07873(6) 0.0442(4) Uani 1 1 d . . .
H6 H 0.2379 0.6198 -0.0601 0.053 Uiso 1 1 calc R . .
C7 C 0.19815(11) 0.77345(11) 0.01027(5) 0.0325(3) Uani 1 1 d . . .
H7 H 0.2550 0.7197 0.0208 0.039 Uiso 1 1 calc R . .
C8 C 0.09688(11) 0.92520(11) 0.07103(5) 0.0310(3) Uani 1 1 d . . .
H8 H 0.0726 1.0007 0.0741 0.037 Uiso 1 1 calc R . .
C9 C 0.02402(11) 0.85629(11) 0.03429(5) 0.0304(3) Uani 1 1 d . . .
C10 C 0.08509(11) 0.74692(10) 0.03848(5) 0.0303(3) Uani 1 1 d . . .
C11 C 0.01898(13) 0.64764(12) 0.02074(6) 0.0420(3) Uani 1 1 d . . .
H11A H -0.0470 0.6683 -0.0002 0.050 Uiso 1 1 calc R . .
H11B H 0.0662 0.6004 -0.0010 0.050 Uiso 1 1 calc R . .
C12 C -0.01624(15) 0.59195(13) 0.07246(7) 0.0473(4) Uani 1 1 d . . .
H12A H -0.0950 0.5697 0.0706 0.057 Uiso 1 1 calc R . .
H12B H 0.0304 0.5287 0.0789 0.057 Uiso 1 1 calc R . .
C13 C 0.09671(11) 0.73931(10) 0.10078(5) 0.0308(3) Uani 1 1 d . . .
C14 C 0.21260(12) 0.70270(12) 0.12277(6) 0.0368(3) Uani 1 1 d . . .
C15 C 0.24956(13) 0.78348(13) 0.16278(6) 0.0416(3) Uani 1 1 d . . .
C16 C 0.34443(16) 0.77994(16) 0.19631(7) 0.0582(5) Uani 1 1 d . . .
H16 H 0.3961 0.7234 0.1942 0.070 Uiso 1 1 calc R . .
C17 C 0.35907(19) 0.86268(18) 0.23253(7) 0.0699(6) Uani 1 1 d . . .
H17 H 0.4219 0.8625 0.2552 0.084 Uiso 1 1 calc R . .
C18 C 0.28176(19) 0.94589(17) 0.23571(6) 0.0663(6) Uani 1 1 d . . .
H18 H 0.2926 0.9999 0.2613 0.080 Uiso 1 1 calc R . .
C19 C 0.18859(17) 0.95138(14) 0.20200(6) 0.0524(4) Uani 1 1 d . . .
H19 H 0.1375 1.0084 0.2042 0.063 Uiso 1 1 calc R . .
C20 C 0.17400(13) 0.86887(12) 0.16485(5) 0.0380(3) Uani 1 1 d . . .
C21 C 0.08320(12) 0.85777(10) 0.12308(5) 0.0322(3) Uani 1 1 d . . .
C22 C 0.00121(18) 0.62384(15) 0.16926(7) 0.0585(5) Uani 1 1 d . . .
H22A H 0.0595 0.5698 0.1711 0.088 Uiso 1 1 calc R . .
H22B H -0.0711 0.5912 0.1765 0.088 Uiso 1 1 calc R . .
H22C H 0.0160 0.6790 0.1955 0.088 Uiso 1 1 calc R . .
N1 N -0.00006(10) 0.67179(9) 0.11552(5) 0.0383(3) Uani 1 1 d . . .
O1 O 0.26073(10) 0.62073(10) 0.11004(5) 0.0524(3) Uani 1 1 d . . .
O2 O -0.02636(9) 0.87780(9) 0.14390(4) 0.0432(3) Uani 1 1 d . . .
O3 O -0.05973(8) 0.87849(9) 0.00936(4) 0.0423(3) Uani 1 1 d . . .
S1 S 0.23630(3) 0.90616(3) 0.040379(14) 0.03508(13) Uani 1 1 d . . .
H2O H -0.0614(18) 0.8213(19) 0.1375(8) 0.068(7) 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 1.388(2) . ?
C1 C6 1.391(2) . ?
C1 C7 1.5186(18) . ?
C2 C3 1.385(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C10 1.5414(18) . ?
C7 S1 1.8599(13) . ?
C7 H7 0.9800 . ?
C8 C9 1.5155(18) . ?
C8 C21 1.5460(18) . ?
C8 S1 1.8267(13) . ?
C8 H8 0.9800 . ?
C9 O3 1.1974(16) . ?
C9 C10 1.5370(18) . ?
C10 C11 1.5205(18) . ?
C10 C13 1.5546(18) . ?
C11 C12 1.515(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N1 1.468(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N1 1.4610(17) . ?
C13 C14 1.5398(19) . ?
C13 C21 1.5753(17) . ?
C14 O1 1.2047(18) . ?
C14 C15 1.475(2) . ?
C15 C20 1.383(2) . ?
C15 C16 1.395(2) . ?
C16 C17 1.374(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.378(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.386(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.497(2) . ?
C21 O2 1.4134(17) . ?
C22 N1 1.459(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O2 H2O 0.83(2) . ?

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 118.69(13) . . ?
C2 C1 C7 123.10(13) . . ?
C6 C1 C7 118.16(13) . . ?
C3 C2 C1 120.56(15) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 120.27(17) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.68(15) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.33(16) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 120.47(16) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C1 C7 C10 112.70(11) . . ?
C1 C7 S1 114.21(10) . . ?
C10 C7 S1 102.42(8) . . ?
C1 C7 H7 109.1 . . ?
C10 C7 H7 109.1 . . ?
S1 C7 H7 109.1 . . ?
C9 C8 C21 98.01(10) . . ?
C9 C8 S1 100.80(8) . . ?
C21 C8 S1 111.84(9) . . ?
C9 C8 H8 114.7 . . ?
C21 C8 H8 114.7 . . ?
S1 C8 H8 114.7 . . ?
O3 C9 C8 130.48(13) . . ?
O3 C9 C10 128.59(12) . . ?
C8 C9 C10 100.92(10) . . ?
C11 C10 C9 116.88(11) . . ?
C11 C10 C7 118.97(11) . . ?
C9 C10 C7 100.77(10) . . ?
C11 C10 C13 106.51(11) . . ?
C9 C10 C13 99.32(10) . . ?
C7 C10 C13 112.84(10) . . ?
C12 C11 C10 105.26(12) . . ?
C12 C11 H11A 110.7 . . ?
C10 C11 H11A 110.7 . . ?
C12 C11 H11B 110.7 . . ?
C10 C11 H11B 110.7 . . ?
H11A C11 H11B 108.8 . . ?
N1 C12 C11 105.94(12) . . ?
N1 C12 H12A 110.5 . . ?
C11 C12 H12A 110.5 . . ?
N1 C12 H12B 110.5 . . ?
C11 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
N1 C13 C14 115.87(11) . . ?
N1 C13 C10 102.40(10) . . ?
C14 C13 C10 116.63(11) . . ?
N1 C13 C21 111.44(10) . . ?
C14 C13 C21 103.84(10) . . ?
C10 C13 C21 106.49(10) . . ?
O1 C14 C15 127.45(14) . . ?
O1 C14 C13 124.98(13) . . ?
C15 C14 C13 107.53(12) . . ?
C20 C15 C16 121.24(15) . . ?
C20 C15 C14 110.64(13) . . ?
C16 C15 C14 128.11(16) . . ?
C17 C16 C15 117.88(19) . . ?
C17 C16 H16 121.1 . . ?
C15 C16 H16 121.1 . . ?
C16 C17 C18 120.77(17) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C19 121.88(17) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C20 117.68(18) . . ?
C18 C19 H19 121.2 . . ?
C20 C19 H19 121.2 . . ?
C15 C20 C19 120.50(15) . . ?
C15 C20 C21 111.42(12) . . ?
C19 C20 C21 128.08(15) . . ?
O2 C21 C20 112.64(11) . . ?
O2 C21 C8 107.82(11) . . ?
C20 C21 C8 117.01(11) . . ?
O2 C21 C13 112.59(11) . . ?
C20 C21 C13 104.85(11) . . ?
C8 C21 C13 101.46(10) . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C22 N1 C13 116.96(12) . . ?
C22 N1 C12 113.11(13) . . ?
C13 N1 C12 107.72(11) . . ?
C21 O2 H2O 103.8(15) . . ?
C8 S1 C7 93.64(6) . . ?

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 0.5(2) . . . . ?
C7 C1 C2 C3 -176.77(14) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C7 C1 C6 C5 176.79(14) . . . . ?
C2 C1 C7 C10 84.17(17) . . . . ?
C6 C1 C7 C10 -93.15(15) . . . . ?
C2 C1 C7 S1 -32.17(18) . . . . ?
C6 C1 C7 S1 150.51(11) . . . . ?
C21 C8 C9 O3 120.19(15) . . . . ?
S1 C8 C9 O3 -125.65(14) . . . . ?
C21 C8 C9 C10 -58.40(11) . . . . ?
S1 C8 C9 C10 55.76(10) . . . . ?
O3 C9 C10 C11 -16.4(2) . . . . ?
C8 C9 C10 C11 162.25(11) . . . . ?
O3 C9 C10 C7 114.10(15) . . . . ?
C8 C9 C10 C7 -67.27(11) . . . . ?
O3 C9 C10 C13 -130.33(14) . . . . ?
C8 C9 C10 C13 48.30(11) . . . . ?
C1 C7 C10 C11 51.03(16) . . . . ?
S1 C7 C10 C11 174.21(10) . . . . ?
C1 C7 C10 C9 -78.12(13) . . . . ?
S1 C7 C10 C9 45.06(10) . . . . ?
C1 C7 C10 C13 176.87(11) . . . . ?
S1 C7 C10 C13 -59.95(11) . . . . ?
C9 C10 C11 C12 -104.18(14) . . . . ?
C7 C10 C11 C12 134.48(13) . . . . ?
C13 C10 C11 C12 5.67(15) . . . . ?
C10 C11 C12 N1 15.53(16) . . . . ?
C11 C10 C13 N1 -24.61(13) . . . . ?
C9 C10 C13 N1 97.16(11) . . . . ?
C7 C10 C13 N1 -156.90(11) . . . . ?
C11 C10 C13 C14 102.98(13) . . . . ?
C9 C10 C13 C14 -135.25(11) . . . . ?
C7 C10 C13 C14 -29.31(15) . . . . ?
C11 C10 C13 C21 -141.70(11) . . . . ?
C9 C10 C13 C21 -19.94(12) . . . . ?
C7 C10 C13 C21 86.01(12) . . . . ?
N1 C13 C14 O1 66.14(19) . . . . ?
C10 C13 C14 O1 -54.54(19) . . . . ?
C21 C13 C14 O1 -171.32(14) . . . . ?
N1 C13 C14 C15 -111.80(13) . . . . ?
C10 C13 C14 C15 127.53(12) . . . . ?
C21 C13 C14 C15 10.74(14) . . . . ?
O1 C14 C15 C20 177.71(15) . . . . ?
C13 C14 C15 C20 -4.42(16) . . . . ?
O1 C14 C15 C16 -3.6(3) . . . . ?
C13 C14 C15 C16 174.29(15) . . . . ?
C20 C15 C16 C17 1.7(3) . . . . ?
C14 C15 C16 C17 -176.93(16) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C16 C17 C18 C19 -1.7(3) . . . . ?
C17 C18 C19 C20 0.9(3) . . . . ?
C16 C15 C20 C19 -2.5(2) . . . . ?
C14 C15 C20 C19 176.29(14) . . . . ?
C16 C15 C20 C21 176.71(14) . . . . ?
C14 C15 C20 C21 -4.47(17) . . . . ?
C18 C19 C20 C15 1.2(2) . . . . ?
C18 C19 C20 C21 -177.88(14) . . . . ?
C15 C20 C21 O2 133.91(13) . . . . ?
C19 C20 C21 O2 -46.9(2) . . . . ?
C15 C20 C21 C8 -100.31(14) . . . . ?
C19 C20 C21 C8 78.85(19) . . . . ?
C15 C20 C21 C13 11.15(15) . . . . ?
C19 C20 C21 C13 -169.68(14) . . . . ?
C9 C8 C21 O2 -75.10(12) . . . . ?
S1 C8 C21 O2 179.81(9) . . . . ?
C9 C8 C21 C20 156.75(12) . . . . ?
S1 C8 C21 C20 51.67(14) . . . . ?
C9 C8 C21 C13 43.37(11) . . . . ?
S1 C8 C21 C13 -61.71(11) . . . . ?
N1 C13 C21 O2 -10.29(15) . . . . ?
C14 C13 C21 O2 -135.71(11) . . . . ?
C10 C13 C21 O2 100.62(12) . . . . ?
N1 C13 C21 C20 112.50(12) . . . . ?
C14 C13 C21 C20 -12.92(13) . . . . ?
C10 C13 C21 C20 -136.59(11) . . . . ?
N1 C13 C21 C8 -125.28(11) . . . . ?
C14 C13 C21 C8 109.30(11) . . . . ?
C10 C13 C21 C8 -14.37(13) . . . . ?
C14 C13 N1 C22 35.84(18) . . . . ?
C10 C13 N1 C22 163.92(13) . . . . ?
C21 C13 N1 C22 -82.60(15) . . . . ?
C14 C13 N1 C12 -92.83(14) . . . . ?
C10 C13 N1 C12 35.25(14) . . . . ?
C21 C13 N1 C12 148.74(12) . . . . ?
C11 C12 N1 C22 -163.60(14) . . . . ?
C11 C12 N1 C13 -32.77(16) . . . . ?
C9 C8 S1 C7 -25.10(9) . . . . ?
C21 C8 S1 C7 78.15(10) . . . . ?
C1 C7 S1 C8 110.29(10) . . . . ?
C10 C7 S1 C8 -11.87(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.035
