# 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_x1208002
_database_code_depnum_ccdc_archive 'CCDC 1529498'
_audit_update_record             
;
2017-01-24 deposited with the CCDC.
2017-02-15 downloaded from the CCDC.
;
_audit_creation_date             2012-08-06
_audit_creation_method           
;
  Olex2 1.2-beta
  (compiled May  9 2012 12:37:22, GUI svn.r4230)
;
_chemical_name_common            ?
_chemical_name_systematic        
'(7S,8aS)-octahydro-5,5-dimethylindolizin-7-ol 9, acetic acid salt monohydrate'
_chemical_formula_moiety         'C10 H20 N O, C2 H3 O2, H2 O'
_chemical_formula_sum            'C12 H25 N O4'
_chemical_formula_weight         247.33
_chemical_absolute_configuration ad
_chemical_melting_point          352-354
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   8.20560(10)
_cell_length_b                   11.9665(2)
_cell_length_c                   13.8857(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1363.47(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9253
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.07
_cell_measurement_theta_min      3.69
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9095
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0954 before and 0.0539 after correction.
The Ratio of minimum to maximum transmission is 0.9095.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.408
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.128
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11121
_diffrn_reflns_theta_full        70.07
_diffrn_reflns_theta_max         70.07
_diffrn_reflns_theta_min         4.88
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_number_gt                2489
_reflns_number_total             2542
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.08(18)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2542
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0717P)²+0.2001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1031
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.66919(15) 0.14777(9) 0.51343(7) 0.0249(3) Uani 1 1 d . . .
H1 H 0.7161 0.0916 0.4900 0.037 Uiso 1 1 calc R . .
N1 N 0.85470(14) 0.31135(10) 0.69981(8) 0.0171(3) Uani 1 1 d . . .
H1A H 0.8336 0.2908 0.7632 0.020 Uiso 1 1 calc R . .
C1 C 0.93295(18) 0.21168(12) 0.65261(10) 0.0186(3) Uani 1 1 d . . .
H1B H 0.9517 0.2284 0.5829 0.022 Uiso 1 1 calc R . .
C2 C 1.09700(19) 0.20735(13) 0.70454(10) 0.0223(3) Uani 1 1 d . . .
H2A H 1.1800 0.1696 0.6643 0.027 Uiso 1 1 calc R . .
H2B H 1.0872 0.1669 0.7664 0.027 Uiso 1 1 calc R . .
C3 C 1.14305(19) 0.33088(14) 0.72163(11) 0.0232(3) Uani 1 1 d . . .
H3A H 1.1820 0.3420 0.7884 0.028 Uiso 1 1 calc R . .
H3B H 1.2300 0.3545 0.6766 0.028 Uiso 1 1 calc R . .
C4 C 0.98654(18) 0.39772(13) 0.70372(10) 0.0199(3) Uani 1 1 d . . .
H4A H 0.9667 0.4514 0.7567 0.024 Uiso 1 1 calc R . .
H4B H 0.9932 0.4393 0.6422 0.024 Uiso 1 1 calc R . .
C5 C 0.69199(18) 0.34647(12) 0.65668(10) 0.0196(3) Uani 1 1 d . . .
C6 C 0.58293(19) 0.24165(13) 0.65790(11) 0.0230(3) Uani 1 1 d . . .
H6A H 0.5518 0.2262 0.7255 0.028 Uiso 1 1 calc R . .
H6B H 0.4816 0.2589 0.6221 0.028 Uiso 1 1 calc R . .
C7 C 0.65638(19) 0.13525(13) 0.61547(10) 0.0218(3) Uani 1 1 d . . .
H7 H 0.5816 0.0713 0.6296 0.026 Uiso 1 1 calc R . .
C8 C 0.82197(19) 0.11119(12) 0.66123(10) 0.0207(3) Uani 1 1 d . . .
H8A H 0.8069 0.0922 0.7300 0.025 Uiso 1 1 calc R . .
H8B H 0.8728 0.0463 0.6289 0.025 Uiso 1 1 calc R . .
C9 C 0.71418(19) 0.39429(13) 0.55546(10) 0.0236(3) Uani 1 1 d . . .
H9A H 0.7739 0.4651 0.5593 0.035 Uiso 1 1 calc R . .
H9B H 0.6071 0.4073 0.5263 0.035 Uiso 1 1 calc R . .
H9C H 0.7757 0.3412 0.5160 0.035 Uiso 1 1 calc R . .
C10 C 0.6190(2) 0.43523(14) 0.72328(11) 0.0255(3) Uani 1 1 d . . .
H10A H 0.6109 0.4052 0.7888 0.038 Uiso 1 1 calc R . .
H10B H 0.5102 0.4558 0.7002 0.038 Uiso 1 1 calc R . .
H10C H 0.6892 0.5015 0.7235 0.038 Uiso 1 1 calc R . .
O2 O 0.54318(15) 0.61349(9) 0.43143(8) 0.0274(3) Uani 1 1 d . . .
O3 O 0.68481(15) 0.76215(10) 0.38262(7) 0.0263(3) Uani 1 1 d . . .
C11 C 0.6267(3) 0.74426(18) 0.55014(11) 0.0429(5) Uani 1 1 d . . .
H11A H 0.5698 0.8160 0.5553 0.064 Uiso 1 1 calc R . .
H11B H 0.7413 0.7541 0.5681 0.064 Uiso 1 1 calc R . .
H11C H 0.5756 0.6899 0.5934 0.064 Uiso 1 1 calc R . .
C12 C 0.6163(2) 0.70220(14) 0.44735(10) 0.0232(3) Uani 1 1 d . . .
O4 O 0.31887(15) 0.53635(9) 0.56338(8) 0.0243(3) Uani 1 1 d . . .
H4C H 0.266(3) 0.593(2) 0.5804(18) 0.052(7) Uiso 1 1 d . . .
H4D H 0.388(3) 0.5584(19) 0.5215(16) 0.043(6) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0309(6) 0.0237(5) 0.0202(5) -0.0048(4) -0.0068(4) 0.0048(5)
N1 0.0177(6) 0.0183(6) 0.0152(5) 0.0003(4) -0.0010(4) 0.0017(5)
C1 0.0193(7) 0.0206(7) 0.0161(6) -0.0002(5) 0.0001(5) 0.0046(6)
C2 0.0198(7) 0.0259(7) 0.0213(7) -0.0003(6) -0.0017(5) 0.0057(6)
C3 0.0193(7) 0.0285(8) 0.0219(7) 0.0022(6) -0.0019(5) 0.0002(6)
C4 0.0203(7) 0.0206(7) 0.0188(7) 0.0019(5) -0.0011(5) -0.0024(6)
C5 0.0168(7) 0.0216(7) 0.0205(7) -0.0019(6) -0.0027(6) 0.0032(6)
C6 0.0187(7) 0.0275(8) 0.0228(7) -0.0023(6) -0.0005(6) -0.0004(6)
C7 0.0246(8) 0.0201(7) 0.0207(7) -0.0010(5) -0.0024(6) -0.0028(6)
C8 0.0264(8) 0.0182(6) 0.0175(6) 0.0001(5) -0.0017(6) 0.0032(6)
C9 0.0256(8) 0.0239(7) 0.0213(7) 0.0010(6) -0.0057(6) 0.0041(6)
C10 0.0231(8) 0.0259(8) 0.0276(8) -0.0061(6) -0.0030(6) 0.0062(7)
O2 0.0339(6) 0.0258(5) 0.0224(5) -0.0006(4) -0.0003(4) -0.0061(5)
O3 0.0327(6) 0.0285(6) 0.0178(5) -0.0015(4) 0.0001(4) -0.0083(5)
C11 0.0569(13) 0.0503(11) 0.0213(8) -0.0046(8) 0.0040(8) -0.0294(10)
C12 0.0244(7) 0.0271(8) 0.0180(7) 0.0007(6) -0.0023(6) -0.0019(6)
O4 0.0278(6) 0.0204(5) 0.0249(5) -0.0014(4) 0.0032(5) 0.0006(5)

_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 H1 0.8400 . ?
O1 C7 1.4287(18) . ?
N1 H1A 0.9300 . ?
N1 C1 1.5047(18) . ?
N1 C4 1.4973(19) . ?
N1 C5 1.5224(17) . ?
C1 H1B 1.0000 . ?
C1 C2 1.5279(19) . ?
C1 C8 1.513(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.544(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.533(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.541(2) . ?
C5 C9 1.5284(19) . ?
C5 C10 1.530(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.527(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.527(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O2 C12 1.239(2) . ?
O3 C12 1.2800(19) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 C12 1.5158(19) . ?
O4 H4C 0.83(3) . ?
O4 H4D 0.85(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
C7 O1 H1 109.5 . . ?
C1 N1 H1A 106.4 . . ?
C1 N1 C5 114.94(11) . . ?
C4 N1 H1A 106.4 . . ?
C4 N1 C1 104.75(11) . . ?
C4 N1 C5 117.22(11) . . ?
C5 N1 H1A 106.4 . . ?
N1 C1 H1B 109.2 . . ?
N1 C1 C2 101.38(11) . . ?
N1 C1 C8 109.79(11) . . ?
C2 C1 H1B 109.2 . . ?
C8 C1 H1B 109.2 . . ?
C8 C1 C2 117.77(12) . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C1 C2 C3 104.81(12) . . ?
H2A C2 H2B 108.9 . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C2 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
H3A C3 H3B 108.7 . . ?
C4 C3 C2 105.63(12) . . ?
C4 C3 H3A 110.6 . . ?
C4 C3 H3B 110.6 . . ?
N1 C4 C3 104.53(11) . . ?
N1 C4 H4A 110.8 . . ?
N1 C4 H4B 110.8 . . ?
C3 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
N1 C5 C6 106.28(11) . . ?
N1 C5 C9 111.14(12) . . ?
N1 C5 C10 107.29(11) . . ?
C9 C5 C6 112.58(12) . . ?
C9 C5 C10 110.02(13) . . ?
C10 C5 C6 109.33(13) . . ?
C5 C6 H6A 108.2 . . ?
C5 C6 H6B 108.2 . . ?
H6A C6 H6B 107.3 . . ?
C7 C6 C5 116.44(13) . . ?
C7 C6 H6A 108.2 . . ?
C7 C6 H6B 108.2 . . ?
O1 C7 C6 108.92(12) . . ?
O1 C7 H7 108.7 . . ?
O1 C7 C8 111.52(13) . . ?
C6 C7 H7 108.7 . . ?
C6 C7 C8 110.35(12) . . ?
C8 C7 H7 108.7 . . ?
C1 C8 C7 110.65(12) . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
O2 C12 O3 124.57(14) . . ?
O2 C12 C11 118.65(14) . . ?
O3 C12 C11 116.78(15) . . ?
H4C O4 H4D 107(2) . . ?

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
O1 H1 O4 0.84 1.90 2.7387(16) 179.1 3_556
N1 H1A O3 0.93 1.78 2.7060(15) 172.1 2_665
O4 H4C O3 0.83(3) 1.93(3) 2.7544(17) 169(3) 3_466
O4 H4D O2 0.85(3) 1.90(3) 2.7563(16) 177(2) .

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
O1 C7 C8 C1 67.33(15) . . . . ?
N1 C1 C2 C3 -35.48(14) . . . . ?
N1 C1 C8 C7 57.95(14) . . . . ?
N1 C5 C6 C7 -50.27(15) . . . . ?
C1 N1 C4 C3 -35.28(13) . . . . ?
C1 N1 C5 C6 54.07(14) . . . . ?
C1 N1 C5 C9 -68.74(15) . . . . ?
C1 N1 C5 C10 170.94(12) . . . . ?
C1 C2 C3 C4 14.57(15) . . . . ?
C2 C1 C8 C7 173.19(12) . . . . ?
C2 C3 C4 N1 12.26(15) . . . . ?
C4 N1 C1 C2 44.12(13) . . . . ?
C4 N1 C1 C8 169.40(11) . . . . ?
C4 N1 C5 C6 177.78(11) . . . . ?
C4 N1 C5 C9 54.97(15) . . . . ?
C4 N1 C5 C10 -65.35(16) . . . . ?
C5 N1 C1 C2 174.22(11) . . . . ?
C5 N1 C1 C8 -60.50(15) . . . . ?
C5 N1 C4 C3 -164.02(11) . . . . ?
C5 C6 C7 O1 -70.45(16) . . . . ?
C5 C6 C7 C8 52.28(17) . . . . ?
C6 C7 C8 C1 -53.87(15) . . . . ?
C8 C1 C2 C3 -155.24(12) . . . . ?
C9 C5 C6 C7 71.63(17) . . . . ?
C10 C5 C6 C7 -165.77(13) . . . . ?

_exptl_crystal_recrystallization_method 
'Crystallized from diethyl ether (Et2O) solution'
