# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1405639'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-07-16 downloaded from the CCDC.
;

_audit_creation_date             2015-04-06T17:43:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
'N-(tert-butyl)-1-(4-chlorophenethyl)-5-oxo-2-(pyridin-3-yl)pyrrolidine-2-carboxamide '
_chemical_formula_moiety         'C22 H26 Cl N3 O2'
_chemical_formula_sum            'C22 H26 Cl N3 O2'
_chemical_formula_weight         399.913

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.6870(4)
_cell_length_b                   9.1043(3)
_cell_length_c                   21.0968(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.623(3)
_cell_angle_gamma                90
_cell_volume                     2029.47(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     1.54184

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.845
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_number            8247
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.184
_diffrn_reflns_theta_max         73.417
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.97
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.97
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.97
_reflns_number_total             3967
_reflns_number_gt                3277
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#
_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11) 
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0655P)²+0.7462P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3967
_refine_ls_number_parameters     357
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1276
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.062

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.13179(5) 0.19103(6) 0.20938(2) 0.03244(17) Uani 1 d . .
O1 O -0.61462(14) 0.36312(16) -0.19299(6) 0.0237(3) Uani 1 d . .
O2 O -0.43598(15) -0.13471(17) -0.04516(7) 0.0306(4) Uani 1 d . .
N2 N -0.43185(15) 0.09056(17) -0.09179(7) 0.0171(3) Uani 1 d . .
N3 N -0.61553(15) 0.30986(18) -0.08780(8) 0.0178(3) Uani 1 d . .
N1 N -0.21906(17) 0.4429(2) -0.16952(9) 0.0299(4) Uani 1 d . .
C2 C -0.36570(17) 0.2388(2) -0.17727(8) 0.0174(4) Uani 1 d . .
C10 C -0.57590(17) 0.2911(2) -0.14490(9) 0.0178(4) Uani 1 d . .
C6 C -0.47750(17) 0.1692(2) -0.15154(8) 0.0165(4) Uani 1 d . .
C11 C -0.71080(17) 0.4215(2) -0.07585(9) 0.0183(4) Uani 1 d . .
C20 C 0.03231(18) 0.1691(2) 0.13654(9) 0.0220(4) Uani 1 d . .
C19 C 0.04323(19) 0.2655(2) 0.08710(10) 0.0223(4) Uani 1 d . .
C1 C -0.32464(19) 0.3787(2) -0.15676(9) 0.0224(4) Uani 1 d . .
C15 C -0.33936(19) 0.1492(2) -0.03975(9) 0.0204(4) Uani 1 d . .
C17 C -0.11821(18) 0.1281(2) 0.01869(9) 0.0212(4) Uani 1 d . .
C18 C -0.03285(18) 0.2433(2) 0.02821(9) 0.0222(4) Uani 1 d . .
C21 C -0.0528(2) 0.0533(2) 0.12911(10) 0.0254(4) Uani 1 d . .
C9 C -0.46744(19) -0.0514(2) -0.09036(10) 0.0230(4) Uani 1 d . .
C7 C -0.5488(2) 0.0465(2) -0.19442(10) 0.0243(4) Uani 1 d . .
C22 C -0.1278(2) 0.0342(2) 0.07029(10) 0.0254(4) Uani 1 d . .
C3 C -0.2919(2) 0.1627(2) -0.21568(9) 0.0250(4) Uani 1 d . .
C16 C -0.20254(19) 0.1033(2) -0.04447(9) 0.0239(4) Uani 1 d . .
C13 C -0.6665(2) 0.5748(2) -0.09232(11) 0.0266(4) Uani 1 d . .
C12 C -0.83887(19) 0.3870(2) -0.11580(10) 0.0247(4) Uani 1 d . .
C14 C -0.7218(2) 0.4142(3) -0.00473(10) 0.0271(5) Uani 1 d . .
C4 C -0.1844(2) 0.2297(3) -0.23096(10) 0.0317(5) Uani 1 d . .
C5 C -0.1517(2) 0.3674(3) -0.20669(11) 0.0337(5) Uani 1 d . .
C8 C -0.5510(4) -0.0855(3) -0.15239(15) 0.0497(8) Uani 1 d . .
H15B H -0.347(2) 0.257(3) -0.0382(11) 0.020(6) Uiso 1 d . .
H15A H -0.363(2) 0.111(3) -0.0014(13) 0.027(6) Uiso 1 d . .
H16A H -0.204(2) -0.002(3) -0.0546(11) 0.024(6) Uiso 1 d . .
H16B H -0.168(2) 0.154(3) -0.0785(12) 0.024(6) Uiso 1 d . .
H3 H -0.311(2) 0.068(3) -0.2297(12) 0.030(7) Uiso 1 d . .
H1 H -0.372(2) 0.438(3) -0.1311(12) 0.023(6) Uiso 1 d . .
H5 H -0.081(3) 0.412(3) -0.2146(12) 0.030(7) Uiso 1 d . .
H4 H -0.137(3) 0.186(3) -0.2564(13) 0.032(7) Uiso 1 d . .
H7A H -0.628(3) 0.077(4) -0.2132(16) 0.057(10) Uiso 1 d . .
H8A H -0.502(5) -0.157(6) -0.173(2) 0.099(16) Uiso 1 d . .
H7B H -0.513(3) 0.021(4) -0.2303(16) 0.050(9) Uiso 1 d . .
H8B H -0.608(5) -0.139(6) -0.154(2) 0.095(16) Uiso 1 d . .
H18 H -0.024(2) 0.311(3) -0.0074(12) 0.023(6) Uiso 1 d . .
H19 H 0.098(2) 0.344(3) 0.0949(12) 0.026(6) Uiso 1 d . .
H22 H -0.187(2) -0.045(3) 0.0640(12) 0.030(7) Uiso 1 d . .
H21 H -0.056(3) -0.013(3) 0.1640(14) 0.038(7) Uiso 1 d . .
H0 H -0.588(2) 0.252(3) -0.0572(11) 0.013(5) Uiso 1 d . .
H12C H -0.904(2) 0.454(3) -0.1073(12) 0.026(6) Uiso 1 d . .
H13C H -0.729(2) 0.640(3) -0.0861(12) 0.023(6) Uiso 1 d . .
H14B H -0.746(3) 0.325(3) 0.0068(13) 0.033(7) Uiso 1 d . .
H14A H -0.783(2) 0.484(3) 0.0059(12) 0.027(6) Uiso 1 d . .
H12B H -0.833(3) 0.394(3) -0.1608(14) 0.035(7) Uiso 1 d . .
H14C H -0.641(3) 0.433(3) 0.0218(13) 0.035(7) Uiso 1 d . .
H12A H -0.867(3) 0.287(4) -0.1060(14) 0.043(8) Uiso 1 d . .
H13A H -0.585(3) 0.598(4) -0.0674(15) 0.050(9) Uiso 1 d . .
H13B H -0.655(3) 0.585(3) -0.1398(14) 0.041(8) Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C20 1.7440(19) . ?
O1 C10 1.226(2) . ?
O2 C9 1.225(3) . ?
N2 C9 1.349(3) . ?
N2 C15 1.464(2) . ?
N2 C6 1.468(2) . ?
N3 C10 1.346(2) . ?
N3 C11 1.487(2) . ?
N1 C5 1.333(3) . ?
N1 C1 1.334(3) . ?
C2 C1 1.395(3) . ?
C2 C3 1.396(3) . ?
C2 C6 1.523(3) . ?
C10 C6 1.550(3) . ?
C6 C7 1.562(3) . ?
C11 C14 1.524(3) . ?
C11 C12 1.528(3) . ?
C11 C13 1.531(3) . ?
C20 C19 1.381(3) . ?
C20 C21 1.386(3) . ?
C19 C18 1.394(3) . ?
C15 C16 1.538(3) . ?
C17 C18 1.385(3) . ?
C17 C22 1.400(3) . ?
C17 C16 1.510(3) . ?
C21 C22 1.383(3) . ?
C9 C8 1.502(3) . ?
C7 C8 1.496(3) . ?
C3 C4 1.380(3) . ?
C4 C5 1.380(4) . ?

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
C9 N2 C15 119.58(16) . . ?
C9 N2 C6 115.34(16) . . ?
C15 N2 C6 124.50(15) . . ?
C10 N3 C11 123.61(16) . . ?
C5 N1 C1 116.2(2) . . ?
C1 C2 C3 116.99(19) . . ?
C1 C2 C6 119.77(17) . . ?
C3 C2 C6 122.86(18) . . ?
O1 C10 N3 124.07(18) . . ?
O1 C10 C6 117.22(16) . . ?
N3 C10 C6 118.70(16) . . ?
N2 C6 C2 109.36(14) . . ?
N2 C6 C10 114.48(15) . . ?
C2 C6 C10 108.27(15) . . ?
N2 C6 C7 102.66(15) . . ?
C2 C6 C7 115.58(16) . . ?
C10 C6 C7 106.61(15) . . ?
N3 C11 C14 107.05(15) . . ?
N3 C11 C12 110.22(15) . . ?
C14 C11 C12 109.83(17) . . ?
N3 C11 C13 109.98(16) . . ?
C14 C11 C13 109.58(17) . . ?
C12 C11 C13 110.13(17) . . ?
C19 C20 C21 121.76(18) . . ?
C19 C20 Cl1 118.89(16) . . ?
C21 C20 Cl1 119.33(16) . . ?
C20 C19 C18 118.48(19) . . ?
N1 C1 C2 125.0(2) . . ?
N2 C15 C16 113.20(16) . . ?
C18 C17 C22 118.25(18) . . ?
C18 C17 C16 122.32(18) . . ?
C22 C17 C16 119.42(19) . . ?
C17 C18 C19 121.51(19) . . ?
C22 C21 C20 118.61(19) . . ?
O2 C9 N2 124.42(19) . . ?
O2 C9 C8 127.4(2) . . ?
N2 C9 C8 108.16(18) . . ?
C8 C7 C6 106.32(17) . . ?
C21 C22 C17 121.4(2) . . ?
C4 C3 C2 118.6(2) . . ?
C17 C16 C15 110.46(16) . . ?
C5 C4 C3 119.2(2) . . ?
N1 C5 C4 123.9(2) . . ?
C7 C8 C9 106.84(19) . . ?


# END of CIF
_chemical_melting_point          432-434
_exptl_crystal_recrystallization_method 'Slow evaporation of CDCl3 solution'
