# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_BB98M
_database_code_depnum_ccdc_archive 'CCDC 1493300'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2017-03-09 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(4S)-4-(4-chlorobenzoyl)-2-methylhexahydropyrrolo[3,4-a]pyrrolizine-1,3(2H,4H)-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 Cl N2 O3'
_chemical_formula_sum            'C17 H17 Cl N2 O3'
_chemical_formula_weight         332.77

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'
Cl Cl 0.1484 0.1585 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.4653(16)
_cell_length_b                   8.3351(11)
_cell_length_c                   16.192(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.902(2)
_cell_angle_gamma                90
_cell_volume                     1571.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6242
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      26.88

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.260
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16635
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.786
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3595
_reflns_number_gt                2940
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0707P)²+0.4904P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3595
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1368
_refine_ls_wR_factor_gt          0.1279
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.62255(16) 0.0960(2) 0.16003(11) 0.0482(4) Uani 1 1 d . . . . .
C2 C 0.54050(15) 0.0001(2) 0.17357(12) 0.0486(4) Uani 1 1 d . . . . .
H2 H 0.4743 -0.0276 0.1266 0.058 Uiso 1 1 calc R U . . .
C3 C 0.55777(14) -0.0545(2) 0.25771(12) 0.0454(4) Uani 1 1 d . . . . .
H3 H 0.5027 -0.1193 0.2674 0.055 Uiso 1 1 calc R U . . .
C4 C 0.65647(13) -0.01372(19) 0.32825(11) 0.0410(3) Uani 1 1 d . . . . .
C5 C 0.73959(15) 0.0786(2) 0.31167(12) 0.0524(4) Uani 1 1 d . . . . .
H5 H 0.8072 0.1038 0.3580 0.063 Uiso 1 1 calc R U . . .
C6 C 0.72348(17) 0.1330(3) 0.22818(13) 0.0565(5) Uani 1 1 d . . . . .
H6 H 0.7797 0.1940 0.2176 0.068 Uiso 1 1 calc R U . . .
C7 C 0.67126(13) -0.07505(19) 0.41819(11) 0.0420(4) Uani 1 1 d . . . . .
C8 C 0.75387(14) 0.01638(19) 0.49646(10) 0.0408(3) Uani 1 1 d . . . . .
H8 H 0.8290 0.0265 0.4903 0.049 Uiso 1 1 calc R U . . .
C9 C 0.76725(15) -0.0600(2) 0.58649(11) 0.0447(4) Uani 1 1 d . . . . .
H9 H 0.7422 -0.1723 0.5798 0.054 Uiso 1 1 calc R U . . .
C10 C 0.88846(17) -0.0434(2) 0.65069(12) 0.0544(4) Uani 1 1 d . . . . .
C11 C 0.9921(2) 0.1004(3) 0.79143(16) 0.0873(8) Uani 1 1 d . . . . .
H11A H 1.0268 0.0061 0.8241 0.131 Uiso 1 1 calc R U . . .
H11B H 0.9733 0.1741 0.8298 0.131 Uiso 1 1 calc R U . . .
H11C H 1.0449 0.1505 0.7684 0.131 Uiso 1 1 calc R U . . .
C12 C 0.7790(2) 0.1087(2) 0.70965(13) 0.0596(5) Uani 1 1 d . . . . .
C13 C 0.69426(16) 0.0428(2) 0.62474(12) 0.0484(4) Uani 1 1 d . . . . .
H13 H 0.6368 -0.0238 0.6370 0.058 Uiso 1 1 calc R U . . .
C14 C 0.63420(15) 0.1680(2) 0.55122(13) 0.0487(4) Uani 1 1 d . . . . .
H14 H 0.5570 0.1292 0.5165 0.058 Uiso 1 1 calc R U . . .
C15 C 0.6259(2) 0.3417(2) 0.57720(17) 0.0651(5) Uani 1 1 d . . . . .
H15A H 0.5521 0.3871 0.5420 0.078 Uiso 1 1 calc R U . . .
H15B H 0.6352 0.3492 0.6392 0.078 Uiso 1 1 calc R U . . .
C16 C 0.7212(3) 0.4280(3) 0.5600(2) 0.0962(10) Uani 1 1 d . . . . .
H16A H 0.6903 0.5148 0.5184 0.115 Uiso 1 1 calc R U . . .
H16B H 0.7742 0.4730 0.6145 0.115 Uiso 1 1 calc R U . . .
C17 C 0.7816(2) 0.3107(2) 0.52296(17) 0.0665(6) Uani 1 1 d . . . . .
H17A H 0.7974 0.3568 0.4735 0.080 Uiso 1 1 calc R U . . .
H17B H 0.8535 0.2774 0.5676 0.080 Uiso 1 1 calc R U . . .
Cl1 Cl 0.59816(5) 0.17599(7) 0.05549(3) 0.06544(19) Uani 1 1 d . . . . .
N1 N 0.88777(15) 0.0558(2) 0.71858(10) 0.0590(4) Uani 1 1 d . . . . .
N2 N 0.70250(12) 0.17432(15) 0.49393(9) 0.0438(3) Uani 1 1 d . . . . .
O1 O 0.61502(12) -0.18705(16) 0.42796(9) 0.0605(4) Uani 1 1 d . . . . .
O2 O 0.97370(13) -0.1029(2) 0.64482(11) 0.0818(5) Uani 1 1 d . . . . .
O3 O 0.7583(2) 0.1928(2) 0.76297(11) 0.0921(6) Uani 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(3) . ?
C1 C6 1.380(3) . ?
C1 Cl1 1.7421(18) . ?
C2 C3 1.378(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(2) . ?
C4 C7 1.491(2) . ?
C5 C6 1.371(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.211(2) . ?
C7 C8 1.522(2) . ?
C8 N2 1.458(2) . ?
C8 C9 1.545(2) . ?
C8 H8 0.9800 . ?
C9 C10 1.504(3) . ?
C9 C13 1.532(2) . ?
C9 H9 0.9800 . ?
C10 O2 1.207(2) . ?
C10 N1 1.378(3) . ?
C11 N1 1.458(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O3 1.209(2) . ?
C12 N1 1.383(3) . ?
C12 C13 1.508(3) . ?
C13 C14 1.559(3) . ?
C13 H13 0.9800 . ?
C14 N2 1.467(2) . ?
C14 C15 1.522(3) . ?
C14 H14 0.9800 . ?
C15 C16 1.497(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.484(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N2 1.467(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 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 C1 C6 121.32(16) . . ?
C2 C1 Cl1 119.69(14) . . ?
C6 C1 Cl1 118.97(14) . . ?
C1 C2 C3 119.10(16) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 120.81(16) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 118.58(16) . . ?
C3 C4 C7 118.92(15) . . ?
C5 C4 C7 122.46(15) . . ?
C6 C5 C4 121.06(17) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 119.03(17) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
O1 C7 C4 121.06(15) . . ?
O1 C7 C8 121.90(15) . . ?
C4 C7 C8 116.91(14) . . ?
N2 C8 C7 105.60(13) . . ?
N2 C8 C9 107.30(13) . . ?
C7 C8 C9 113.11(13) . . ?
N2 C8 H8 110.2 . . ?
C7 C8 H8 110.2 . . ?
C9 C8 H8 110.2 . . ?
C10 C9 C13 105.30(15) . . ?
C10 C9 C8 110.96(14) . . ?
C13 C9 C8 105.73(13) . . ?
C10 C9 H9 111.5 . . ?
C13 C9 H9 111.5 . . ?
C8 C9 H9 111.5 . . ?
O2 C10 N1 124.5(2) . . ?
O2 C10 C9 127.10(19) . . ?
N1 C10 C9 108.43(16) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 N1 124.1(2) . . ?
O3 C12 C13 127.1(2) . . ?
N1 C12 C13 108.73(16) . . ?
C12 C13 C9 104.39(15) . . ?
C12 C13 C14 116.20(15) . . ?
C9 C13 C14 104.97(14) . . ?
C12 C13 H13 110.3 . . ?
C9 C13 H13 110.3 . . ?
C14 C13 H13 110.3 . . ?
N2 C14 C15 104.62(15) . . ?
N2 C14 C13 106.15(13) . . ?
C15 C14 C13 119.16(17) . . ?
N2 C14 H14 108.8 . . ?
C15 C14 H14 108.8 . . ?
C13 C14 H14 108.8 . . ?
C16 C15 C14 105.60(17) . . ?
C16 C15 H15A 110.6 . . ?
C14 C15 H15A 110.6 . . ?
C16 C15 H15B 110.6 . . ?
C14 C15 H15B 110.6 . . ?
H15A C15 H15B 108.8 . . ?
C17 C16 C15 108.00(17) . . ?
C17 C16 H16A 110.1 . . ?
C15 C16 H16A 110.1 . . ?
C17 C16 H16B 110.1 . . ?
C15 C16 H16B 110.1 . . ?
H16A C16 H16B 108.4 . . ?
N2 C17 C16 105.07(18) . . ?
N2 C17 H17A 110.7 . . ?
C16 C17 H17A 110.7 . . ?
N2 C17 H17B 110.7 . . ?
C16 C17 H17B 110.7 . . ?
H17A C17 H17B 108.8 . . ?
C10 N1 C12 113.13(16) . . ?
C10 N1 C11 122.7(2) . . ?
C12 N1 C11 124.1(2) . . ?
C8 N2 C14 107.33(12) . . ?
C8 N2 C17 116.88(15) . . ?
C14 N2 C17 107.49(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
C6 C1 C2 C3 2.7(3) . . . . ?
Cl1 C1 C2 C3 -176.08(14) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 -2.3(3) . . . . ?
C2 C3 C4 C7 179.78(15) . . . . ?
C3 C4 C5 C6 2.1(3) . . . . ?
C7 C4 C5 C6 179.92(17) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C2 C1 C6 C5 -2.9(3) . . . . ?
Cl1 C1 C6 C5 175.87(16) . . . . ?
C3 C4 C7 O1 17.6(2) . . . . ?
C5 C4 C7 O1 -160.18(17) . . . . ?
C3 C4 C7 C8 -158.38(15) . . . . ?
C5 C4 C7 C8 23.8(2) . . . . ?
O1 C7 C8 N2 -110.67(17) . . . . ?
C4 C7 C8 N2 65.32(17) . . . . ?
O1 C7 C8 C9 6.4(2) . . . . ?
C4 C7 C8 C9 -177.63(13) . . . . ?
N2 C8 C9 C10 -99.84(16) . . . . ?
C7 C8 C9 C10 144.11(15) . . . . ?
N2 C8 C9 C13 13.83(17) . . . . ?
C7 C8 C9 C13 -102.21(15) . . . . ?
C13 C9 C10 O2 -178.6(2) . . . . ?
C8 C9 C10 O2 -64.7(3) . . . . ?
C13 C9 C10 N1 0.25(19) . . . . ?
C8 C9 C10 N1 114.19(16) . . . . ?
O3 C12 C13 C9 -177.6(2) . . . . ?
N1 C12 C13 C9 1.67(19) . . . . ?
O3 C12 C13 C14 67.3(3) . . . . ?
N1 C12 C13 C14 -113.38(18) . . . . ?
C10 C9 C13 C12 -1.13(18) . . . . ?
C8 C9 C13 C12 -118.68(15) . . . . ?
C10 C9 C13 C14 121.58(15) . . . . ?
C8 C9 C13 C14 4.04(17) . . . . ?
C12 C13 C14 N2 94.29(18) . . . . ?
C9 C13 C14 N2 -20.43(17) . . . . ?
C12 C13 C14 C15 -23.3(3) . . . . ?
C9 C13 C14 C15 -137.99(18) . . . . ?
N2 C14 C15 C16 -19.0(3) . . . . ?
C13 C14 C15 C16 99.3(2) . . . . ?
C14 C15 C16 C17 1.4(3) . . . . ?
C15 C16 C17 N2 16.8(3) . . . . ?
O2 C10 N1 C12 179.8(2) . . . . ?
C9 C10 N1 C12 0.9(2) . . . . ?
O2 C10 N1 C11 0.3(3) . . . . ?
C9 C10 N1 C11 -178.56(18) . . . . ?
O3 C12 N1 C10 177.7(2) . . . . ?
C13 C12 N1 C10 -1.6(2) . . . . ?
O3 C12 N1 C11 -2.9(3) . . . . ?
C13 C12 N1 C11 177.78(18) . . . . ?
C7 C8 N2 C14 93.46(15) . . . . ?
C9 C8 N2 C14 -27.46(17) . . . . ?
C7 C8 N2 C17 -145.81(16) . . . . ?
C9 C8 N2 C17 93.28(18) . . . . ?
C15 C14 N2 C8 156.75(15) . . . . ?
C13 C14 N2 C8 29.89(17) . . . . ?
C15 C14 N2 C17 30.2(2) . . . . ?
C13 C14 N2 C17 -96.61(17) . . . . ?
C16 C17 N2 C8 -150.1(2) . . . . ?
C16 C17 N2 C14 -29.5(2) . . . . ?

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.044

