# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_11209c
_database_code_depnum_ccdc_archive 'CCDC 999697'
_audit_update_record             
;
2014-04-26 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_IUPAC             Dibenzyl[(2R)-2-chloropropyl]amine
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H20 Cl N'
_chemical_formula_sum            'C17 H20 Cl N'
_chemical_formula_weight         273.79
_chemical_absolute_configuration rmad

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   9.547(3)
_cell_length_b                   7.1510(19)
_cell_length_c                   12.171(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.479(3)
_cell_angle_gamma                90.00
_cell_volume                     773.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2969
_cell_measurement_theta_min      3.37
_cell_measurement_theta_max      26.30

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9225
_exptl_absorpt_correction_T_max  0.9724
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008/1)'

_exptl_special_details           'Prof. J. Chong  - IIT'

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4374
_diffrn_reflns_av_R_equivalents  0.0094
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         26.32
_reflns_number_total             3064
_reflns_number_gt                2884
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0354P)²+0.1000P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_number_reflns         3064
_refine_ls_number_parameters     173
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0722
_refine_ls_wR_factor_gt          0.0702
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
Cl1 Cl 0.50048(5) 0.93906(6) 0.63625(4) 0.06224(15) Uani 1 1 d . . .
N1 N 0.82881(13) 0.55897(17) 0.77322(11) 0.0358(3) Uani 1 1 d . . .
C1 C 0.48861(19) 0.5614(3) 0.65139(17) 0.0562(5) Uani 1 1 d . . .
H1A H 0.5394 0.4403 0.6588 0.084 Uiso 1 1 calc R . .
H1B H 0.4013 0.5650 0.5771 0.084 Uiso 1 1 calc R . .
H1C H 0.4550 0.5783 0.7178 0.084 Uiso 1 1 calc R . .
C2 C 0.59619(17) 0.7157(2) 0.65207(14) 0.0392(3) Uani 1 1 d . . .
H2A H 0.6295 0.6978 0.5839 0.047 Uiso 1 1 calc R . .
C3 C 0.73422(16) 0.7238(2) 0.76563(14) 0.0389(3) Uani 1 1 d . . .
H3A H 0.7923 0.8389 0.7667 0.047 Uiso 1 1 calc R . .
H3B H 0.7025 0.7271 0.8345 0.047 Uiso 1 1 calc R . .
C4 C 0.93186(17) 0.5893(2) 0.71059(16) 0.0424(4) Uani 1 1 d . . .
H4A H 1.0169 0.6681 0.7598 0.051 Uiso 1 1 calc R . .
H4B H 0.8783 0.6576 0.6363 0.051 Uiso 1 1 calc R . .
C5 C 0.99250(16) 0.4085(2) 0.68232(13) 0.0365(3) Uani 1 1 d . . .
C6 C 1.14515(17) 0.3881(2) 0.70492(15) 0.0451(4) Uani 1 1 d . . .
H6A H 1.2126 0.4860 0.7433 0.054 Uiso 1 1 calc R . .
C7 C 1.20018(19) 0.2272(3) 0.67233(17) 0.0512(4) Uani 1 1 d . . .
H7A H 1.3049 0.2153 0.6883 0.061 Uiso 1 1 calc R . .
C8 C 1.1044(2) 0.0853(3) 0.61727(15) 0.0515(4) Uani 1 1 d . . .
H8A H 1.1422 -0.0248 0.5942 0.062 Uiso 1 1 calc R . .
C9 C 0.9517(2) 0.1025(2) 0.59512(15) 0.0499(4) Uani 1 1 d . . .
H9A H 0.8849 0.0036 0.5576 0.060 Uiso 1 1 calc R . .
C10 C 0.89668(17) 0.2632(2) 0.62751(15) 0.0436(4) Uani 1 1 d . . .
H10A H 0.7920 0.2742 0.6120 0.052 Uiso 1 1 calc R . .
C11 C 0.91028(16) 0.5028(2) 0.89617(14) 0.0416(4) Uani 1 1 d . . .
H11A H 0.9543 0.6150 0.9441 0.050 Uiso 1 1 calc R . .
H11B H 0.9938 0.4180 0.8998 0.050 Uiso 1 1 calc R . .
C12 C 0.80798(16) 0.4053(2) 0.94733(13) 0.0381(3) Uani 1 1 d . . .
C13 C 0.79217(18) 0.4639(3) 1.05074(14) 0.0480(4) Uani 1 1 d . . .
H13A H 0.8466 0.5700 1.0914 0.058 Uiso 1 1 calc R . .
C14 C 0.6977(2) 0.3693(3) 1.09562(16) 0.0554(5) Uani 1 1 d . . .
H14A H 0.6877 0.4113 1.1664 0.066 Uiso 1 1 calc R . .
C15 C 0.6187(2) 0.2153(3) 1.03809(15) 0.0540(4) Uani 1 1 d . . .
H15A H 0.5534 0.1512 1.0684 0.065 Uiso 1 1 calc R . .
C16 C 0.6349(2) 0.1545(3) 0.93596(16) 0.0511(4) Uani 1 1 d . . .
H16A H 0.5814 0.0472 0.8963 0.061 Uiso 1 1 calc R . .
C17 C 0.72803(17) 0.2481(2) 0.89099(14) 0.0429(3) Uani 1 1 d . . .
H17A H 0.7378 0.2046 0.8204 0.051 Uiso 1 1 calc R . .

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
Cl1 0.0652(3) 0.0624(3) 0.0517(2) 0.0014(2) 0.0127(2) 0.0336(2)
N1 0.0320(6) 0.0315(7) 0.0445(7) -0.0015(5) 0.0147(5) 0.0042(5)
C1 0.0378(9) 0.0691(13) 0.0585(11) 0.0019(9) 0.0137(8) -0.0060(8)
C2 0.0367(7) 0.0424(9) 0.0408(8) -0.0005(7) 0.0168(6) 0.0110(6)
C3 0.0361(7) 0.0345(8) 0.0446(8) -0.0055(7) 0.0131(6) 0.0050(6)
C4 0.0376(8) 0.0293(8) 0.0653(10) 0.0005(7) 0.0248(7) -0.0002(6)
C5 0.0379(7) 0.0310(8) 0.0444(8) 0.0027(6) 0.0196(6) 0.0026(6)
C6 0.0405(8) 0.0422(9) 0.0588(10) 0.0001(7) 0.0256(8) 0.0009(7)
C7 0.0469(9) 0.0519(10) 0.0631(11) 0.0050(9) 0.0299(8) 0.0126(8)
C8 0.0703(12) 0.0443(9) 0.0449(9) 0.0034(8) 0.0270(8) 0.0235(9)
C9 0.0622(11) 0.0369(9) 0.0441(9) -0.0050(7) 0.0119(8) 0.0016(8)
C10 0.0400(8) 0.0382(9) 0.0501(9) -0.0004(7) 0.0136(7) 0.0031(7)
C11 0.0314(7) 0.0401(9) 0.0467(9) -0.0047(6) 0.0063(6) 0.0027(6)
C12 0.0352(7) 0.0367(8) 0.0359(7) -0.0007(6) 0.0052(6) 0.0084(6)
C13 0.0441(8) 0.0488(10) 0.0418(8) -0.0111(8) 0.0048(7) 0.0065(7)
C14 0.0561(10) 0.0729(13) 0.0367(9) -0.0059(8) 0.0164(8) 0.0109(9)
C15 0.0537(9) 0.0664(12) 0.0424(9) 0.0064(9) 0.0182(8) 0.0017(9)
C16 0.0594(11) 0.0471(9) 0.0465(10) -0.0019(8) 0.0189(8) -0.0070(8)
C17 0.0507(8) 0.0408(8) 0.0375(8) -0.0044(7) 0.0166(7) 0.0013(7)

_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
Cl1 C2 1.8148(16) . ?
N1 C4 1.4646(19) . ?
N1 C11 1.467(2) . ?
N1 C3 1.4672(18) . ?
C1 C2 1.506(3) . ?
C2 C3 1.522(2) . ?
C4 C5 1.507(2) . ?
C5 C10 1.384(2) . ?
C5 C6 1.388(2) . ?
C6 C7 1.382(2) . ?
C7 C8 1.366(3) . ?
C8 C9 1.388(3) . ?
C9 C10 1.380(2) . ?
C11 C12 1.508(2) . ?
C12 C13 1.386(2) . ?
C12 C17 1.391(2) . ?
C13 C14 1.390(3) . ?
C14 C15 1.373(3) . ?
C15 C16 1.378(3) . ?
C16 C17 1.376(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
C4 N1 C11 111.41(12) . . ?
C4 N1 C3 111.32(12) . . ?
C11 N1 C3 111.61(12) . . ?
C1 C2 C3 113.26(14) . . ?
C1 C2 Cl1 109.19(11) . . ?
C3 C2 Cl1 107.33(11) . . ?
N1 C3 C2 109.57(12) . . ?
N1 C4 C5 112.29(12) . . ?
C10 C5 C6 118.51(14) . . ?
C10 C5 C4 120.85(13) . . ?
C6 C5 C4 120.55(14) . . ?
C7 C6 C5 120.83(16) . . ?
C8 C7 C6 120.20(15) . . ?
C7 C8 C9 119.74(15) . . ?
C10 C9 C8 120.08(17) . . ?
C9 C10 C5 120.64(15) . . ?
N1 C11 C12 111.48(12) . . ?
C13 C12 C17 118.01(15) . . ?
C13 C12 C11 122.51(15) . . ?
C17 C12 C11 119.47(14) . . ?
C12 C13 C14 120.79(16) . . ?
C15 C14 C13 120.32(16) . . ?
C14 C15 C16 119.37(18) . . ?
C15 C16 C17 120.53(17) . . ?
C16 C17 C12 120.99(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
C4 N1 C3 C2 85.72(15) . . . . ?
C11 N1 C3 C2 -149.11(13) . . . . ?
C1 C2 C3 N1 68.44(17) . . . . ?
Cl1 C2 C3 N1 -170.97(10) . . . . ?
C11 N1 C4 C5 73.49(17) . . . . ?
C3 N1 C4 C5 -161.23(13) . . . . ?
N1 C4 C5 C10 50.4(2) . . . . ?
N1 C4 C5 C6 -133.15(15) . . . . ?
C10 C5 C6 C7 0.7(2) . . . . ?
C4 C5 C6 C7 -175.84(15) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C8 C9 C10 C5 -0.1(3) . . . . ?
C6 C5 C10 C9 -0.6(2) . . . . ?
C4 C5 C10 C9 175.91(15) . . . . ?
C4 N1 C11 C12 -159.20(12) . . . . ?
C3 N1 C11 C12 75.68(16) . . . . ?
N1 C11 C12 C13 -125.28(15) . . . . ?
N1 C11 C12 C17 56.08(18) . . . . ?
C17 C12 C13 C14 -0.8(2) . . . . ?
C11 C12 C13 C14 -179.44(15) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C14 C15 C16 C17 -0.7(3) . . . . ?
C15 C16 C17 C12 0.1(3) . . . . ?
C13 C12 C17 C16 0.6(2) . . . . ?
C11 C12 C17 C16 179.31(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.32
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.024
