# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1469407'
_audit_update_record             
;
2016-03-18 deposited with the CCDC.
2016-05-06 downloaded from the CCDC.
;
#data_ap6 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'[(+)-(1S,2R)-Z-diethylaminocarbonyl-2-aminomethyl-1-phenyl-cyclopropane]'
_chemical_formula_moiety         'C19 H28 N2 O2'
_chemical_formula_sum            'C19 H28 N2 O2'
_chemical_formula_weight         316.43

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   10.3704(6)
_cell_length_b                   11.6346(6)
_cell_length_c                   15.6401(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1887.06(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9967
_cell_measurement_theta_min      2.181
_cell_measurement_theta_max      26.896

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_T_max  0.744
_exptl_absorpt_process_details   'SADABS, Bruker, 1997'

_exptl_special_details           
; 
 The racemic mixture of the two enantiomers of the examined compound
 crystallizes by forming separately monocrystals of one enantiomer and
 monocrystals of the other enantiomer. The crystal used for data 
 collection was cut from a relatively large crystal (2.00x1.18x0.90mm)
 whose absolute configuration has been determined by HPLC analysis
 on chiral column, allowing to assign the stereochemistry to the
 two asymmetric carbons (1S, 2R) present in the structure.
;

_diffrn_ambient_temperature      296(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  'Bruker SMART APEX'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            31195
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0095
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.182
_diffrn_reflns_theta_max         28.428
_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 0.566
_diffrn_reflns_point_group_measured_fraction_full 0.573
_reflns_number_total             2687
_reflns_number_gt                2469
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP III ( Burnett&Johnson, 1996)'
_computing_publication_material  'SHELXL-97,PARST (Nardelli, 1995)'

_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     
'w=1/[σ²(Fo²)+(0.0588P)²+0.1551P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   4.6(15)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2687
_refine_ls_number_parameters     215
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.1003
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.40332(15) 0.80187(9) 0.29832(8) 0.0608(3) Uani 1 1 d . . .
O2 O 0.78439(19) 0.60333(12) 0.39470(10) 0.0804(5) Uani 1 1 d . . .
N1 N 0.38530(12) 0.64930(10) 0.38465(7) 0.0401(3) Uani 1 1 d . . .
N2 N 0.68038(12) 0.49875(11) 0.29636(8) 0.0428(3) Uani 1 1 d . . .
H1 H 0.6606(19) 0.4295(17) 0.2766(12) 0.051 Uiso 1 1 d . . .
C1 C 0.39250(14) 0.61878(12) 0.22870(8) 0.0375(3) Uani 1 1 d . . .
C2 C 0.52084(14) 0.57300(13) 0.19570(9) 0.0409(3) Uani 1 1 d . . .
H2 H 0.5162 0.4985 0.1665 0.049 Uiso 1 1 calc R . .
C3 C 0.45568(16) 0.67017(15) 0.15017(9) 0.0481(4) Uani 1 1 d . . .
H3A H 0.4168 0.6541 0.0950 0.058 Uiso 1 1 calc R . .
H3B H 0.4935 0.7461 0.1555 0.058 Uiso 1 1 calc R . .
C4 C 0.26925(15) 0.55292(13) 0.21588(9) 0.0411(3) Uani 1 1 d . . .
C5 C 0.26561(18) 0.43594(14) 0.19759(11) 0.0510(4) Uani 1 1 d . . .
H5 H 0.3422 0.3945 0.1945 0.061 Uiso 1 1 calc R . .
C6 C 0.1491(2) 0.38046(18) 0.18398(12) 0.0638(5) Uani 1 1 d . . .
H6 H 0.1482 0.3023 0.1717 0.077 Uiso 1 1 calc R . .
C7 C 0.0351(2) 0.4399(2) 0.18850(15) 0.0732(6) Uani 1 1 d . . .
H7 H -0.0428 0.4026 0.1786 0.088 Uiso 1 1 calc R . .
C8 C 0.0370(2) 0.5552(2) 0.20785(17) 0.0783(6) Uani 1 1 d . . .
H8 H -0.0401 0.5955 0.2122 0.094 Uiso 1 1 calc R . .
C9 C 0.15249(17) 0.61167(17) 0.22089(13) 0.0606(5) Uani 1 1 d . . .
H9 H 0.1523 0.6899 0.2332 0.073 Uiso 1 1 calc R . .
C10 C 0.39467(14) 0.69652(12) 0.30697(9) 0.0391(3) Uani 1 1 d . . .
C11 C 0.38376(18) 0.72608(16) 0.45978(10) 0.0527(4) Uani 1 1 d . . .
H11A H 0.3384 0.6883 0.5062 0.063 Uiso 1 1 calc R . .
H11B H 0.3367 0.7955 0.4455 0.063 Uiso 1 1 calc R . .
C12 C 0.5168(2) 0.7582(2) 0.48955(13) 0.0689(6) Uani 1 1 d . . .
H12A H 0.5593 0.8022 0.4459 0.103 Uiso 1 1 calc R . .
H12B H 0.5655 0.6897 0.5009 0.103 Uiso 1 1 calc R . .
H12C H 0.5106 0.8032 0.5408 0.103 Uiso 1 1 calc R . .
C13 C 0.38963(17) 0.52593(14) 0.40222(10) 0.0479(3) Uani 1 1 d . . .
H13A H 0.4557 0.5112 0.4447 0.058 Uiso 1 1 calc R . .
H13B H 0.4139 0.4857 0.3503 0.058 Uiso 1 1 calc R . .
C14 C 0.2622(3) 0.4782(2) 0.43415(17) 0.0819(7) Uani 1 1 d . . .
H14A H 0.1969 0.4901 0.3916 0.123 Uiso 1 1 calc R . .
H14B H 0.2381 0.5168 0.4860 0.123 Uiso 1 1 calc R . .
H14C H 0.2711 0.3974 0.4451 0.123 Uiso 1 1 calc R . .
C15 C 0.64536(15) 0.59585(14) 0.24281(10) 0.0445(3) Uani 1 1 d . . .
H15A H 0.7137 0.6103 0.2018 0.053 Uiso 1 1 calc R . .
H15B H 0.6357 0.6639 0.2781 0.053 Uiso 1 1 calc R . .
C16 C 0.74855(16) 0.51018(14) 0.36847(10) 0.0461(3) Uani 1 1 d . . .
C17 C 0.77845(18) 0.39884(16) 0.41652(11) 0.0537(4) Uani 1 1 d . . .
H17 H 0.7410 0.3342 0.3850 0.064 Uiso 1 1 calc R . .
C18 C 0.7202(3) 0.4024(3) 0.50482(16) 0.0977(9) Uani 1 1 d . . .
H18A H 0.7500 0.4697 0.5343 0.146 Uiso 1 1 calc R . .
H18B H 0.7455 0.3350 0.5360 0.146 Uiso 1 1 calc R . .
H18C H 0.6279 0.4047 0.5003 0.146 Uiso 1 1 calc R . .
C19 C 0.9237(2) 0.3822(3) 0.42177(17) 0.0832(7) Uani 1 1 d . . .
H19A H 0.9423 0.3127 0.4525 0.125 Uiso 1 1 calc R . .
H19B H 0.9617 0.4463 0.4511 0.125 Uiso 1 1 calc R . .
H19C H 0.9588 0.3771 0.3651 0.125 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 C10 1.2364(18) . ?
O2 C16 1.217(2) . ?
N1 C10 1.3369(18) . ?
N1 C13 1.4620(19) . ?
N1 C11 1.4761(18) . ?
N2 C16 1.3376(19) . ?
N2 C15 1.452(2) . ?
C1 C4 1.504(2) . ?
C1 C3 1.515(2) . ?
C1 C10 1.5223(18) . ?
C1 C2 1.5237(19) . ?
C2 C3 1.497(2) . ?
C2 C15 1.510(2) . ?
C4 C5 1.391(2) . ?
C4 C9 1.393(2) . ?
C5 C6 1.386(3) . ?
C6 C7 1.372(3) . ?
C7 C8 1.375(4) . ?
C8 C9 1.381(3) . ?
C11 C12 1.503(3) . ?
C13 C14 1.518(3) . ?
C16 C17 1.529(2) . ?
C17 C18 1.508(3) . ?
C17 C19 1.521(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
C10 N1 C13 124.89(12) . . ?
C10 N1 C11 118.39(13) . . ?
C13 N1 C11 116.41(13) . . ?
C16 N2 C15 122.75(13) . . ?
C4 C1 C3 117.42(12) . . ?
C4 C1 C10 115.00(12) . . ?
C3 C1 C10 114.28(12) . . ?
C4 C1 C2 121.28(12) . . ?
C3 C1 C2 59.04(10) . . ?
C10 C1 C2 117.86(12) . . ?
C3 C2 C15 119.01(14) . . ?
C3 C2 C1 60.19(9) . . ?
C15 C2 C1 121.33(12) . . ?
C2 C3 C1 60.77(9) . . ?
C5 C4 C9 117.91(16) . . ?
C5 C4 C1 123.30(14) . . ?
C9 C4 C1 118.78(14) . . ?
C6 C5 C4 120.71(17) . . ?
C7 C6 C5 120.56(18) . . ?
C6 C7 C8 119.37(19) . . ?
C7 C8 C9 120.6(2) . . ?
C8 C9 C4 120.81(18) . . ?
O1 C10 N1 120.81(13) . . ?
O1 C10 C1 120.14(13) . . ?
N1 C10 C1 119.05(12) . . ?
N1 C11 C12 112.77(14) . . ?
N1 C13 C14 113.23(17) . . ?
N2 C15 C2 110.99(12) . . ?
O2 C16 N2 122.28(16) . . ?
O2 C16 C17 121.79(14) . . ?
N2 C16 C17 115.92(14) . . ?
C18 C17 C19 110.54(19) . . ?
C18 C17 C16 110.22(18) . . ?
C19 C17 C16 109.57(17) . . ?

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.026

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'methyl tert-butyl ether '
