# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

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

data_majr_Pna21
_database_code_depnum_ccdc_archive 'CCDC 1061074'
_audit_update_record             
;
2015-04-21 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'Rac-2-methyl-1-phenyl-2,3,4,5,6,10b-hexahydro-1H-pyrrolo[2,1-a]isoquinolin-4-ium chloride'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H22 Cl N'
_chemical_formula_weight         299.82

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   7.4474(3)
_cell_length_b                   16.4971(8)
_cell_length_c                   12.9089(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1585.99(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8192
_cell_measurement_theta_min      0.00
_cell_measurement_theta_max      0.00

_exptl_crystal_description       lathe
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.235
_shelx_estimated_absorpt_T_min   0.906
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6619
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   'Bruker SAINT (SADABS)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15505
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.003
_diffrn_reflns_theta_max         33.163
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5870
_reflns_number_gt                5410
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_max     0.930
_reflns_Friedel_fraction_full    0.991

_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 SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0418P)²+0.6000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2354 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.08(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5870
_refine_ls_number_parameters     195
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.0951
_refine_ls_wR_factor_gt          0.0927
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
Cl1 Cl -0.26076(6) 0.35188(3) 0.38809(5) 0.02250(10) Uani 1 1 d . . . . .
N1 N 0.1272(2) 0.39413(9) 0.41509(12) 0.0156(3) Uani 1 1 d . . . . .
H1N H 0.018(4) 0.3764(15) 0.399(2) 0.020(6) Uiso 1 1 d . . . . .
C1 C 0.1093(2) 0.48201(10) 0.44780(14) 0.0138(3) Uani 1 1 d . . . . .
H1 H -0.0163 0.4888 0.4737 0.017 Uiso 1 1 calc R U . . .
C2 C 0.2359(3) 0.49208(11) 0.54457(14) 0.0153(3) Uani 1 1 d . . . . .
H2 H 0.1573 0.5046 0.6053 0.018 Uiso 1 1 calc R U . . .
C3 C 0.3168(3) 0.40686(11) 0.56343(15) 0.0176(3) Uani 1 1 d . . . . .
H3 H 0.4360 0.4030 0.5280 0.021 Uiso 1 1 calc R U . . .
C4 C 0.1843(3) 0.34965(11) 0.51078(16) 0.0190(3) Uani 1 1 d . . . . .
H4A H 0.2427 0.2976 0.4928 0.023 Uiso 1 1 calc R U . . .
H4B H 0.0800 0.3386 0.5563 0.023 Uiso 1 1 calc R U . . .
C5 C 0.1317(2) 0.54139(11) 0.35941(13) 0.0140(3) Uani 1 1 d . . . . .
C6 C 0.1103(2) 0.62391(10) 0.38084(16) 0.0175(3) Uani 1 1 d . . . . .
H6 H 0.0778 0.6407 0.4487 0.021 Uiso 1 1 calc R U . . .
C7 C 0.1358(3) 0.68144(12) 0.30402(16) 0.0217(4) Uani 1 1 d . . . . .
H7 H 0.1210 0.7374 0.3192 0.026 Uiso 1 1 calc R U . . .
C8 C 0.1833(3) 0.65705(13) 0.20451(17) 0.0227(4) Uani 1 1 d . . . . .
H8 H 0.2043 0.6963 0.1521 0.027 Uiso 1 1 calc R U . . .
C9 C 0.1997(3) 0.57532(13) 0.18220(15) 0.0199(4) Uani 1 1 d . . . . .
H9 H 0.2301 0.5589 0.1139 0.024 Uiso 1 1 calc R U . . .
C10 C 0.1720(3) 0.51657(11) 0.25876(14) 0.0158(3) Uani 1 1 d . . . . .
C11 C 0.1860(3) 0.42787(12) 0.23337(15) 0.0189(3) Uani 1 1 d . . . . .
H11A H 0.2707 0.4204 0.1750 0.023 Uiso 1 1 calc R U . . .
H11B H 0.0670 0.4075 0.2112 0.023 Uiso 1 1 calc R U . . .
C12 C 0.2506(3) 0.37908(12) 0.32575(16) 0.0183(3) Uani 1 1 d . . . . .
H12A H 0.2514 0.3206 0.3084 0.022 Uiso 1 1 calc R U . . .
H12B H 0.3744 0.3954 0.3443 0.022 Uiso 1 1 calc R U . . .
C13 C 0.3764(2) 0.55800(10) 0.53913(14) 0.0153(3) Uani 1 1 d . . . . .
C14 C 0.5137(3) 0.55577(12) 0.46554(15) 0.0188(3) Uani 1 1 d . . . . .
H14 H 0.5223 0.5111 0.4194 0.023 Uiso 1 1 calc R U . . .
C15 C 0.6382(3) 0.61861(14) 0.45925(17) 0.0249(4) Uani 1 1 d . . . . .
H15 H 0.7307 0.6168 0.4087 0.030 Uiso 1 1 calc R U . . .
C16 C 0.6270(3) 0.68400(13) 0.5270(2) 0.0291(5) Uani 1 1 d . . . . .
H16 H 0.7102 0.7275 0.5215 0.035 Uiso 1 1 calc R U . . .
C17 C 0.4957(3) 0.68570(12) 0.60174(19) 0.0273(5) Uani 1 1 d . . . . .
H17 H 0.4902 0.7297 0.6491 0.033 Uiso 1 1 calc R U . . .
C18 C 0.3701(3) 0.62275(12) 0.60839(16) 0.0211(4) Uani 1 1 d . . . . .
H18 H 0.2801 0.6242 0.6605 0.025 Uiso 1 1 calc R U . . .
C19 C 0.3405(3) 0.38936(14) 0.67877(17) 0.0253(4) Uani 1 1 d . . . . .
H19A H 0.2225 0.3871 0.7122 0.038 Uiso 1 1 calc R U . . .
H19B H 0.4123 0.4325 0.7105 0.038 Uiso 1 1 calc R U . . .
H19C H 0.4019 0.3373 0.6876 0.038 Uiso 1 1 calc R U . . .


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

 Least-squares planes (x,y,z in crystal coordinates) and deviations from 
 them (* indicates atom used to define plane)

  7.2303(0.0015) x + 0.7898(0.0138) y + 3.0321(0.0101) z = 2.4513(0.0086) 

 *    0.0186(0.0013)  C5
 *   -0.0066(0.0013)  C6
 *   -0.0091(0.0015)  C7
 *    0.0129(0.0015)  C8
 *   -0.0009(0.0014)  C9
 *   -0.0148(0.0013)  C10

 Rms deviation of fitted atoms =   0.0120


  4.4466(0.0048) x - 8.0311(0.0115) y + 8.2306(0.0081) z = 1.6444(0.0102) 

 Angle to previous plane(with approximate esd) = 45.081( 0.069 )

 *   -0.0145(0.0013)  C13
 *    0.0082(0.0014)  C14
 *    0.0051(0.0014)  C15
 *   -0.0123(0.0014)  C16
 *    0.0058(0.0015)  C17
 *    0.0076(0.0014)  C18

 Rms deviation of fitted atoms =   0.0095

;

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
N1 C12 1.495(3) . ?
N1 C4 1.498(3) . ?
N1 C1 1.516(2) . ?
N1 H1N 0.89(3) . ?
C1 C5 1.513(2) . ?
C1 C2 1.574(3) . ?
C1 H1 1.0000 . ?
C2 C13 1.511(3) . ?
C2 C3 1.549(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.526(3) . ?
C3 C19 1.527(3) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.395(3) . ?
C5 C6 1.398(2) . ?
C6 C7 1.386(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.399(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.503(3) . ?
C11 C12 1.517(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.394(3) . ?
C13 C14 1.396(3) . ?
C14 C15 1.393(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.374(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.400(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C12 N1 C4 112.36(15) . . ?
C12 N1 C1 115.32(14) . . ?
C4 N1 C1 105.29(14) . . ?
C12 N1 H1N 109.0(17) . . ?
C4 N1 H1N 107.0(18) . . ?
C1 N1 H1N 107.4(16) . . ?
C5 C1 N1 113.54(14) . . ?
C5 C1 C2 117.65(14) . . ?
N1 C1 C2 105.63(14) . . ?
C5 C1 H1 106.4 . . ?
N1 C1 H1 106.4 . . ?
C2 C1 H1 106.4 . . ?
C13 C2 C3 113.02(16) . . ?
C13 C2 C1 117.00(15) . . ?
C3 C2 C1 105.19(14) . . ?
C13 C2 H2 107.0 . . ?
C3 C2 H2 107.0 . . ?
C1 C2 H2 107.0 . . ?
C4 C3 C19 113.09(16) . . ?
C4 C3 C2 103.87(15) . . ?
C19 C3 C2 111.70(17) . . ?
C4 C3 H3 109.3 . . ?
C19 C3 H3 109.3 . . ?
C2 C3 H3 109.3 . . ?
N1 C4 C3 104.34(14) . . ?
N1 C4 H4A 110.9 . . ?
C3 C4 H4A 110.9 . . ?
N1 C4 H4B 110.9 . . ?
C3 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
C10 C5 C6 119.65(16) . . ?
C10 C5 C1 122.42(16) . . ?
C6 C5 C1 117.94(16) . . ?
C7 C6 C5 120.63(18) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 119.83(18) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 119.74(19) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.98(19) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C5 C10 C9 119.09(17) . . ?
C5 C10 C11 120.25(17) . . ?
C9 C10 C11 120.66(17) . . ?
C10 C11 C12 111.54(16) . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
N1 C12 C11 108.88(15) . . ?
N1 C12 H12A 109.9 . . ?
C11 C12 H12A 109.9 . . ?
N1 C12 H12B 109.9 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C18 C13 C14 118.77(18) . . ?
C18 C13 C2 119.90(18) . . ?
C14 C13 C2 121.33(16) . . ?
C15 C14 C13 120.49(19) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 119.98(19) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 120.4(2) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C3 C19 H19A 109.5 . . ?
C3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C12 N1 C1 C5 30.7(2) . . . . ?
C4 N1 C1 C5 155.12(15) . . . . ?
C12 N1 C1 C2 -99.69(17) . . . . ?
C4 N1 C1 C2 24.75(18) . . . . ?
C5 C1 C2 C13 -2.9(2) . . . . ?
N1 C1 C2 C13 125.00(16) . . . . ?
C5 C1 C2 C3 -129.32(16) . . . . ?
N1 C1 C2 C3 -1.38(18) . . . . ?
C13 C2 C3 C4 -150.68(16) . . . . ?
C1 C2 C3 C4 -21.89(18) . . . . ?
C13 C2 C3 C19 87.1(2) . . . . ?
C1 C2 C3 C19 -144.10(16) . . . . ?
C12 N1 C4 C3 87.09(18) . . . . ?
C1 N1 C4 C3 -39.20(18) . . . . ?
C19 C3 C4 N1 159.03(17) . . . . ?
C2 C3 C4 N1 37.74(18) . . . . ?
N1 C1 C5 C10 -2.4(2) . . . . ?
C2 C1 C5 C10 121.68(19) . . . . ?
N1 C1 C5 C6 177.43(16) . . . . ?
C2 C1 C5 C6 -58.5(2) . . . . ?
C10 C5 C6 C7 -2.7(3) . . . . ?
C1 C5 C6 C7 177.53(17) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C6 C7 C8 C9 1.8(3) . . . . ?
C7 C8 C9 C10 -1.0(3) . . . . ?
C6 C5 C10 C9 3.4(3) . . . . ?
C1 C5 C10 C9 -176.80(17) . . . . ?
C6 C5 C10 C11 -176.81(18) . . . . ?
C1 C5 C10 C11 3.0(3) . . . . ?
C8 C9 C10 C5 -1.6(3) . . . . ?
C8 C9 C10 C11 178.62(19) . . . . ?
C5 C10 C11 C12 -30.4(3) . . . . ?
C9 C10 C11 C12 149.43(18) . . . . ?
C4 N1 C12 C11 -178.55(15) . . . . ?
C1 N1 C12 C11 -57.9(2) . . . . ?
C10 C11 C12 N1 56.1(2) . . . . ?
C3 C2 C13 C18 -121.17(19) . . . . ?
C1 C2 C13 C18 116.42(19) . . . . ?
C3 C2 C13 C14 59.0(2) . . . . ?
C1 C2 C13 C14 -63.4(2) . . . . ?
C18 C13 C14 C15 -2.2(3) . . . . ?
C2 C13 C14 C15 177.62(18) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C14 C15 C16 C17 1.6(3) . . . . ?
C15 C16 C17 C18 -1.6(3) . . . . ?
C14 C13 C18 C17 2.2(3) . . . . ?
C2 C13 C18 C17 -177.69(18) . . . . ?
C16 C17 C18 C13 -0.3(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
N1 H1N Cl1 0.89(3) 2.12(3) 2.9927(17) 167(2) .

_refine_diff_density_max         0.456
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.064

_shelxl_version_number           2013-4

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

data_yk944_P21c
_database_code_depnum_ccdc_archive 'CCDC 1061075'
_audit_update_record             
;
2015-04-21 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
Rac-1-(4-bromophenyl)-3-phenyloctahydropyrrolizin-4-ium-4-yl)trihydroborate
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H23 Br N'
_chemical_formula_weight         357.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   13.9903(5)
_cell_length_b                   6.5457(3)
_cell_length_c                   19.1580(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.3551(8)
_cell_angle_gamma                90
_cell_volume                     1706.97(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9824
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      32.60

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             740
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    2.405
_shelx_estimated_absorpt_T_min   0.523
_shelx_estimated_absorpt_T_max   0.778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5868
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   'Bruker SAINT (SADABS)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23857
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.496
_diffrn_reflns_theta_max         32.679
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6256
_reflns_number_gt                5107
_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 SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0400P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6256
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.007
_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
Br1 Br 0.48304(2) 0.47029(3) 1.18821(2) 0.03121(6) Uani 1 1 d . . . . .
N1 N 0.17698(8) -0.17888(18) 0.83090(6) 0.0164(2) Uani 1 1 d . . . . .
C1 C 0.21498(10) -0.1192(2) 0.91003(7) 0.0171(2) Uani 1 1 d . . . . .
H1 H 0.2086(13) -0.234(3) 0.9356(10) 0.021 Uiso 1 1 d . U . . .
C2 C 0.32282(10) -0.0556(2) 0.91731(7) 0.0181(2) Uani 1 1 d . . . . .
H2 H 0.3626(13) -0.180(3) 0.9227(10) 0.022 Uiso 1 1 d . U . . .
C3 C 0.32049(10) 0.0355(2) 0.84340(7) 0.0190(2) Uani 1 1 d . . . . .
H3A H 0.2876(14) 0.165(3) 0.8392(10) 0.023 Uiso 1 1 d . U . . .
H3B H 0.3841(15) 0.056(3) 0.8334(11) 0.023 Uiso 1 1 d . U . . .
C4 C 0.26015(10) -0.1225(2) 0.79364(7) 0.0176(2) Uani 1 1 d . . . . .
H4 H 0.3007(13) -0.241(3) 0.7985(10) 0.021 Uiso 1 1 d . U . . .
C5 C 0.14560(11) 0.0483(2) 0.92394(8) 0.0195(3) Uani 1 1 d . . . . .
H5A H 0.1697(14) 0.178(3) 0.9138(10) 0.023 Uiso 1 1 d . U . . .
H5B H 0.1474(15) 0.053(3) 0.9733(11) 0.023 Uiso 1 1 d . U . . .
C6 C 0.04898(12) -0.0040(2) 0.87136(8) 0.0231(3) Uani 1 1 d . . . . .
H6A H 0.0179(14) -0.127(3) 0.8878(11) 0.028 Uiso 1 1 d . U . . .
H6B H 0.0032(15) 0.101(3) 0.8636(11) 0.028 Uiso 1 1 d . U . . .
C7 C 0.08420(11) -0.0556(2) 0.80423(8) 0.0215(3) Uani 1 1 d . . . . .
H7A H 0.0418(14) -0.136(3) 0.7682(10) 0.026 Uiso 1 1 d . U . . .
H7B H 0.1000(15) 0.074(3) 0.7821(11) 0.026 Uiso 1 1 d . U . . .
C8 C 0.36156(10) 0.0756(2) 0.98265(7) 0.0184(3) Uani 1 1 d . . . . .
C9 C 0.37523(12) -0.0106(2) 1.05094(8) 0.0233(3) Uani 1 1 d . . . . .
H9 H 0.3591(14) -0.150(3) 1.0545(10) 0.028 Uiso 1 1 d . U . . .
C10 C 0.41026(12) 0.1041(3) 1.11269(8) 0.0258(3) Uani 1 1 d . . . . .
H10 H 0.4214(16) 0.047(3) 1.1579(13) 0.031 Uiso 1 1 d . U . . .
C11 C 0.43197(10) 0.3080(3) 1.10559(8) 0.0222(3) Uani 1 1 d . . . . .
C12 C 0.41780(12) 0.3984(3) 1.03905(8) 0.0254(3) Uani 1 1 d . . . . .
H12 H 0.4306(16) 0.534(3) 1.0333(12) 0.030 Uiso 1 1 d . U . . .
C13 C 0.38273(12) 0.2815(2) 0.97774(8) 0.0240(3) Uani 1 1 d . . . . .
H13 H 0.3733(14) 0.345(3) 0.9316(11) 0.029 Uiso 1 1 d . U . . .
C14 C 0.22507(10) -0.0662(2) 0.71531(7) 0.0179(2) Uani 1 1 d . . . . .
C15 C 0.20838(13) -0.2213(2) 0.66412(8) 0.0248(3) Uani 1 1 d . . . . .
H15 H 0.2187(15) -0.360(3) 0.6790(11) 0.030 Uiso 1 1 d . U . . .
C16 C 0.17499(14) -0.1764(3) 0.59169(8) 0.0302(4) Uani 1 1 d . . . . .
H16 H 0.1623(16) -0.279(3) 0.5599(12) 0.036 Uiso 1 1 d . U . . .
C17 C 0.15954(13) 0.0242(3) 0.56853(8) 0.0267(3) Uani 1 1 d . . . . .
H17 H 0.1384(16) 0.057(3) 0.5194(12) 0.032 Uiso 1 1 d . U . . .
C18 C 0.17854(12) 0.1803(2) 0.61896(8) 0.0239(3) Uani 1 1 d . . . . .
H18 H 0.1672(14) 0.321(3) 0.6031(11) 0.029 Uiso 1 1 d . U . . .
C19 C 0.21089(11) 0.1359(2) 0.69169(8) 0.0212(3) Uani 1 1 d . . . . .
H19 H 0.2221(14) 0.249(3) 0.7240(10) 0.025 Uiso 1 1 d . U . . .
C20 C 0.15430(14) -0.4220(3) 0.82484(10) 0.0308(3) Uani 1 1 d . . . . .
H20A H 0.0835(19) -0.459(4) 0.8557(14) 0.046 Uiso 1 1 d . U . . .
H20B H 0.227(2) -0.511(3) 0.8548(15) 0.046 Uiso 1 1 d . U . . .
H20C H 0.1288(19) -0.463(3) 0.7599(14) 0.046 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C11 1.9030(15) . ?
N1 C7 1.5134(18) . ?
N1 C1 1.5365(17) . ?
N1 C4 1.5439(18) . ?
N1 C20 1.622(2) . ?
C1 C5 1.528(2) . ?
C1 C2 1.540(2) . ?
C1 H1 0.912(19) . ?
C2 C8 1.5114(19) . ?
C2 C3 1.530(2) . ?
C2 H2 0.978(19) . ?
C3 C4 1.523(2) . ?
C3 H3A 0.96(2) . ?
C3 H3B 0.96(2) . ?
C4 C14 1.5127(19) . ?
C4 H4 0.954(19) . ?
C5 C6 1.526(2) . ?
C5 H5A 0.95(2) . ?
C5 H5B 0.94(2) . ?
C6 C7 1.518(2) . ?
C6 H6A 1.00(2) . ?
C6 H6B 0.93(2) . ?
C7 H7A 0.96(2) . ?
C7 H7B 1.00(2) . ?
C8 C13 1.388(2) . ?
C8 C9 1.397(2) . ?
C9 C10 1.391(2) . ?
C9 H9 0.95(2) . ?
C10 C11 1.383(2) . ?
C10 H10 0.92(2) . ?
C11 C12 1.377(2) . ?
C12 C13 1.393(2) . ?
C12 H12 0.92(2) . ?
C13 H13 0.96(2) . ?
C14 C15 1.393(2) . ?
C14 C19 1.398(2) . ?
C15 C16 1.389(2) . ?
C15 H15 0.95(2) . ?
C16 C17 1.387(2) . ?
C16 H16 0.90(2) . ?
C17 C18 1.389(2) . ?
C17 H17 0.94(2) . ?
C18 C19 1.393(2) . ?
C18 H18 0.97(2) . ?
C19 H19 0.96(2) . ?
C20 H20A 1.29(3) . ?
C20 H20B 1.20(3) . ?
C20 H20C 1.24(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 N1 C1 105.78(10) . . ?
C7 N1 C4 113.32(11) . . ?
C1 N1 C4 105.64(10) . . ?
C7 N1 C20 111.14(12) . . ?
C1 N1 C20 109.72(11) . . ?
C4 N1 C20 110.92(11) . . ?
C5 C1 N1 105.39(11) . . ?
C5 C1 C2 116.01(12) . . ?
N1 C1 C2 105.46(11) . . ?
C5 C1 H1 110.7(12) . . ?
N1 C1 H1 105.4(12) . . ?
C2 C1 H1 112.9(11) . . ?
C8 C2 C3 118.17(12) . . ?
C8 C2 C1 112.65(12) . . ?
C3 C2 C1 102.16(11) . . ?
C8 C2 H2 107.4(11) . . ?
C3 C2 H2 108.2(11) . . ?
C1 C2 H2 107.8(11) . . ?
C4 C3 C2 101.82(11) . . ?
C4 C3 H3A 111.2(11) . . ?
C2 C3 H3A 109.2(11) . . ?
C4 C3 H3B 112.2(12) . . ?
C2 C3 H3B 114.6(12) . . ?
H3A C3 H3B 107.8(16) . . ?
C14 C4 C3 117.47(12) . . ?
C14 C4 N1 114.23(11) . . ?
C3 C4 N1 103.93(10) . . ?
C14 C4 H4 110.1(11) . . ?
C3 C4 H4 105.1(11) . . ?
N1 C4 H4 104.8(11) . . ?
C6 C5 C1 103.02(12) . . ?
C6 C5 H5A 111.6(11) . . ?
C1 C5 H5A 109.7(12) . . ?
C6 C5 H5B 119.0(12) . . ?
C1 C5 H5B 109.3(12) . . ?
H5A C5 H5B 104.2(16) . . ?
C7 C6 C5 101.42(12) . . ?
C7 C6 H6A 109.8(12) . . ?
C5 C6 H6A 110.9(11) . . ?
C7 C6 H6B 112.1(13) . . ?
C5 C6 H6B 114.3(13) . . ?
H6A C6 H6B 108.2(18) . . ?
N1 C7 C6 104.68(11) . . ?
N1 C7 H7A 106.9(12) . . ?
C6 C7 H7A 117.7(12) . . ?
N1 C7 H7B 109.9(12) . . ?
C6 C7 H7B 108.6(12) . . ?
H7A C7 H7B 108.8(17) . . ?
C13 C8 C9 118.07(13) . . ?
C13 C8 C2 122.47(13) . . ?
C9 C8 C2 119.45(13) . . ?
C10 C9 C8 121.58(15) . . ?
C10 C9 H9 120.1(12) . . ?
C8 C9 H9 118.3(12) . . ?
C11 C10 C9 118.65(14) . . ?
C11 C10 H10 119.4(14) . . ?
C9 C10 H10 121.9(14) . . ?
C12 C11 C10 121.17(14) . . ?
C12 C11 Br1 118.44(12) . . ?
C10 C11 Br1 120.39(11) . . ?
C11 C12 C13 119.47(15) . . ?
C11 C12 H12 122.4(14) . . ?
C13 C12 H12 118.1(14) . . ?
C8 C13 C12 121.03(14) . . ?
C8 C13 H13 119.7(13) . . ?
C12 C13 H13 119.3(13) . . ?
C15 C14 C19 118.28(13) . . ?
C15 C14 C4 118.94(13) . . ?
C19 C14 C4 122.76(12) . . ?
C16 C15 C14 120.78(15) . . ?
C16 C15 H15 119.6(13) . . ?
C14 C15 H15 119.6(13) . . ?
C17 C16 C15 120.76(15) . . ?
C17 C16 H16 120.0(14) . . ?
C15 C16 H16 119.3(14) . . ?
C16 C17 C18 118.90(14) . . ?
C16 C17 H17 121.5(13) . . ?
C18 C17 H17 119.6(13) . . ?
C17 C18 C19 120.53(15) . . ?
C17 C18 H18 119.2(12) . . ?
C19 C18 H18 120.2(12) . . ?
C18 C19 C14 120.70(14) . . ?
C18 C19 H19 117.0(12) . . ?
C14 C19 H19 122.3(12) . . ?
N1 C20 H20A 108.0(11) . . ?
N1 C20 H20B 108.0(12) . . ?
H20A C20 H20B 110.5(17) . . ?
N1 C20 H20C 107.0(11) . . ?
H20A C20 H20C 110.2(17) . . ?
H20B C20 H20C 112.9(17) . . ?

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
C7 N1 C1 C5 -3.88(14) . . . . ?
C4 N1 C1 C5 116.53(11) . . . . ?
C20 N1 C1 C5 -123.85(13) . . . . ?
C7 N1 C1 C2 -127.12(12) . . . . ?
C4 N1 C1 C2 -6.70(13) . . . . ?
C20 N1 C1 C2 112.92(13) . . . . ?
C5 C1 C2 C8 43.64(16) . . . . ?
N1 C1 C2 C8 159.83(11) . . . . ?
C5 C1 C2 C3 -84.18(14) . . . . ?
N1 C1 C2 C3 32.01(13) . . . . ?
C8 C2 C3 C4 -169.48(12) . . . . ?
C1 C2 C3 C4 -45.28(13) . . . . ?
C2 C3 C4 C14 168.61(12) . . . . ?
C2 C3 C4 N1 41.34(13) . . . . ?
C7 N1 C4 C14 -35.26(16) . . . . ?
C1 N1 C4 C14 -150.62(11) . . . . ?
C20 N1 C4 C14 90.55(14) . . . . ?
C7 N1 C4 C3 94.00(13) . . . . ?
C1 N1 C4 C3 -21.36(13) . . . . ?
C20 N1 C4 C3 -140.19(12) . . . . ?
N1 C1 C5 C6 29.22(14) . . . . ?
C2 C1 C5 C6 145.45(12) . . . . ?
C1 C5 C6 C7 -43.24(14) . . . . ?
C1 N1 C7 C6 -23.22(15) . . . . ?
C4 N1 C7 C6 -138.49(12) . . . . ?
C20 N1 C7 C6 95.81(14) . . . . ?
C5 C6 C7 N1 41.23(15) . . . . ?
C3 C2 C8 C13 8.6(2) . . . . ?
C1 C2 C8 C13 -110.27(16) . . . . ?
C3 C2 C8 C9 -172.65(13) . . . . ?
C1 C2 C8 C9 68.52(17) . . . . ?
C13 C8 C9 C10 -0.9(2) . . . . ?
C2 C8 C9 C10 -179.69(14) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C9 C10 C11 C12 1.2(2) . . . . ?
C9 C10 C11 Br1 -178.51(12) . . . . ?
C10 C11 C12 C13 -1.2(2) . . . . ?
Br1 C11 C12 C13 178.47(12) . . . . ?
C9 C8 C13 C12 0.8(2) . . . . ?
C2 C8 C13 C12 179.61(14) . . . . ?
C11 C12 C13 C8 0.2(2) . . . . ?
C3 C4 C14 C15 152.83(14) . . . . ?
N1 C4 C14 C15 -85.05(16) . . . . ?
C3 C4 C14 C19 -25.5(2) . . . . ?
N1 C4 C14 C19 96.58(16) . . . . ?
C19 C14 C15 C16 -2.4(2) . . . . ?
C4 C14 C15 C16 179.21(15) . . . . ?
C14 C15 C16 C17 1.4(3) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C16 C17 C18 C19 -1.1(3) . . . . ?
C17 C18 C19 C14 0.2(2) . . . . ?
C15 C14 C19 C18 1.6(2) . . . . ?
C4 C14 C19 C18 179.95(14) . . . . ?

_refine_diff_density_max         0.702
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.083

_shelxl_version_number           2013-4

