# Electronic Supplementary Material (ESI) for RSC Advances.
# 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).
# 
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# 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 
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data_KLHN53
_database_code_depnum_ccdc_archive 'CCDC 1038709'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;
_audit_creation_date             2014-12-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H25 N O4'
_chemical_formula_sum            'C19 H25 N O4'
_chemical_formula_weight         331.40
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   14.778(3)
_cell_length_b                   6.9181(14)
_cell_length_c                   17.853(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1825.2(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2457
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      0.41
_cell_measurement_wavelength     0.71073
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3465
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.666
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            '95mm CCD camera on \k-goniostat'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_UB_11      0.049678
_diffrn_orient_matrix_UB_12      -0.059198
_diffrn_orient_matrix_UB_13      0.019029
_diffrn_orient_matrix_UB_21      -0.075075
_diffrn_orient_matrix_UB_22      -0.032407
_diffrn_orient_matrix_UB_23      -0.039584
_diffrn_orient_matrix_UB_31      0.112816
_diffrn_orient_matrix_UB_32      0.004502
_diffrn_orient_matrix_UB_33      -0.034721
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_source_target            Mo
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1585
_reflns_number_total             1951
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         1951
_refine_ls_number_restraints     97
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      14.476
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0646P)²+0.8478P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1478
_refine_special_details          
'Methine carbon (C1) and the phenyl group connected to this atom are disordered over two positions. The occupation factors of both components were fixed to 0.5. In addition, ethyl group connected to carboxylate functionalty (C6, O7 and O10) is disordered by symmetry operation (mirror plane). The occupation factors of 0.5 indicate that both components contribute equally to the molecular formula of the structure. Also, certain bond lengths, angles and thermal displacement parameters in the disordered groups were restrained using "DFIX, DANG and ISOR/SIMU" commands.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H4 of C4, H19A of C19A, H20A of C20A, H21 of C21, H20B
  of C20B, {H19B,H8A,H8B} of C19B
 At 1.5 times of:
  {H16A,H16B,H16C} of C16, {H15A,H15B,H15C} of C15, {H9A,H9B,H9C} of C9, H11
  of C19B
2. Restrained distances
 N11-H11
 0.87 with sigma of 0.005
 C9-C8
 1.54 with sigma of 0.01
 H8B-C8 = H8B-H8A
 0.99 with sigma of 0.001
 C18-C19A = C19A-C20A = C20A-C21 = C21-C20B_$1 = C20B_$1-C19B_$1 = C19B_$1-C18
 = C18-C19B = C19B-C20B
 1.39 with sigma of 0.005
 H8A-H8B
 1.615 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
C18 \\sim C19A \\sim C20A \\sim C21 \\sim C20B \\sim C19B: within 2A with sigma
of 0.005 and sigma for terminal atoms of 0.01
Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C20B) \\sim Ueq, Uanis(C21) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4. Others
 Fixed Sof: H5B(0.5) H5A(0.5) H3A(0.5) H3B(0.5) H16A(0.5) H16B(0.5) H16C(0.5)
 C8(0.5) C19A(0.5) H19A(0.5) C4(0.5) H4(0.5) C20A(0.5) H20A(0.5) C9(0.5)
 H9A(0.5) H9B(0.5) H9C(0.5) C21(0.5) H21(0.5) C20B(0.5) H20B(0.5) C19B(0.5)
 H19B(0.5) H8B(0.5)
5.a Ternary CH refined with riding coordinates:
 C4(H4)
5.b Secondary CH2 refined with riding coordinates:
 C5(H5B,H5A), C3(H3A,H3B)
5.c Aromatic/amide H refined with riding coordinates:
 C19A(H19A), C20A(H20A), C21(H21), C20B(H20B), C19B(H19B)
5.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O13 O 0.32623(10) 0.2500 0.63618(9) 0.0415(5) Uani 1 2 d S T P . .
O17 O 0.46680(11) 0.2500 0.68910(10) 0.0503(5) Uani 1 2 d S T P . .
N11 N 0.44310(13) 0.2500 0.56186(11) 0.0381(5) Uani 1 2 d DS T P . .
O10 O 0.39586(12) 0.2500 0.41496(11) 0.0673(7) Uani 1 2 d S T P . .
C5 C 0.64706(16) 0.2500 0.44397(13) 0.0415(6) Uani 1 2 d S T P . .
H5B H 0.6697 0.3821 0.4337 0.050 Uiso 0.5 1 calc R . . . .
H5A H 0.6628 0.1645 0.4014 0.050 Uiso 0.5 1 calc R . . . .
O7 O 0.51074(12) 0.2500 0.33277(9) 0.0553(6) Uani 1 2 d S T P . .
C12 C 0.41721(16) 0.2500 0.63577(13) 0.0365(5) Uani 1 2 d S T P . .
C1 C 0.54684(15) 0.2500 0.45865(13) 0.0357(5) Uani 1 2 d S T P . .
C3 C 0.61395(17) 0.2500 0.57898(14) 0.0489(7) Uani 1 2 d S T P . .
H3A H 0.6084 0.1637 0.6230 0.059 Uiso 0.5 1 calc R . . . .
H3B H 0.6299 0.3819 0.5960 0.059 Uiso 0.5 1 calc R . . . .
C2 C 0.52933(15) 0.2500 0.53291(13) 0.0357(5) Uani 1 2 d S T P . .
C6 C 0.47707(17) 0.2500 0.40230(14) 0.0447(6) Uani 1 2 d S T P . .
C16 C 0.17741(18) 0.2500 0.67799(17) 0.0743(11) Uani 1 2 d S T P . .
H16A H 0.1354 0.2613 0.7202 0.111 Uiso 0.5 1 calc GR . . A -1
H16B H 0.1657 0.1291 0.6511 0.111 Uiso 0.5 1 calc GR . . A -1
H16C H 0.1688 0.3596 0.6440 0.111 Uiso 0.5 1 calc GR . . A -1
C15 C 0.29400(15) 0.0686(4) 0.75047(12) 0.0637(6) Uani 1 1 d . . . . .
H15A H 0.2527 0.0595 0.7933 0.096 Uiso 1 1 calc GR . . . .
H15B H 0.3566 0.0724 0.7685 0.096 Uiso 1 1 calc GR . . . .
H15C H 0.2858 -0.0442 0.7180 0.096 Uiso 1 1 calc GR . . . .
C14 C 0.27392(16) 0.2500 0.70693(13) 0.0434(6) Uani 1 2 d S T P . .
C18 C 0.78098(17) 0.2500 0.53658(14) 0.0538(7) Uani 1 2 d DS TU P . .
C8 C 0.4455(2) 0.2021(7) 0.2723(2) 0.0555(17) Uani 0.5 1 d D U . . .
C19A C 0.8024(3) 0.4428(6) 0.5360(3) 0.0660(10) Uani 0.5 1 d D U . B 1
H19A H 0.7552 0.5326 0.5264 0.079 Uiso 0.5 1 calc R . . B 1
C4 C 0.6856(2) 0.1693(6) 0.52007(18) 0.0446(9) Uani 0.5 1 d . . . B .
H4 H 0.6860 0.0247 0.5200 0.054 Uiso 0.5 1 calc R . . . .
C20A C 0.8878(3) 0.5145(8) 0.5483(3) 0.0765(11) Uani 0.5 1 d D U . B 1
H20A H 0.8997 0.6490 0.5442 0.092 Uiso 0.5 1 calc R . . B 1
C9 C 0.4850(3) 0.2929(11) 0.20337(18) 0.059(2) Uani 0.5 1 d D U . . .
H9A H 0.4944 0.4313 0.2121 0.089 Uiso 0.5 1 calc GR . . . .
H9B H 0.4433 0.2752 0.1612 0.089 Uiso 0.5 1 calc GR . . . .
H9C H 0.5430 0.2314 0.1917 0.089 Uiso 0.5 1 calc GR . . . .
C21 C 0.9546(3) 0.3893(7) 0.5665(4) 0.0709(13) Uani 0.5 1 d D U . B 1
H21 H 1.0099 0.4476 0.5816 0.085 Uiso 0.5 1 calc R . . B 1
C20B C 0.9386(3) 0.3059(6) 0.5687(3) 0.0621(12) Uani 0.5 1 d D U . B 2
H20B H 0.9903 0.3843 0.5775 0.074 Uiso 0.5 1 calc R . . B 2
C19B C 0.8515(2) 0.3762(7) 0.5539(3) 0.0703(10) Uani 0.5 1 d D U . B 2
H19B H 0.8404 0.5114 0.5557 0.084 Uiso 0.5 1 calc R . . B 2
H8A H 0.386(2) 0.2500 0.285(2) 0.084 Uiso 1 2 d DRS T P . .
H8B H 0.4433(19) 0.0595(9) 0.268(3) 0.084 Uiso 0.5 1 d DR . . . .
H11 H 0.402(2) 0.2500 0.5272(16) 0.106 Uiso 1 2 d DRS T P . .


_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
O13 C12 1.345(3) . ?
O13 C14 1.481(3) . ?
O17 C12 1.201(3) . ?
N11 C12 1.374(3) . ?
N11 C2 1.375(3) . ?
N11 H11 0.870(5) . ?
O10 C6 1.221(3) . ?
C5 H5B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 C1 1.504(3) . ?
C5 C4 1.575(4) . ?
O7 C6 1.337(3) . ?
O7 C8 1.485(4) . ?
O7 C8 1.485(4) 8_565 ?
C1 C2 1.351(3) . ?
C1 C6 1.440(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.497(3) . ?
C3 C4 1.594(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 C14 1.517(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 C14 1.506(3) . ?
C14 C15 1.506(3) 8_565 ?
C18 C19A 1.371(4) . ?
C18 C19A 1.371(4) 8_565 ?
C18 C4 1.545(4) 8_565 ?
C18 C4 1.545(4) . ?
C18 C19B 1.395(3) . ?
C18 C19B 1.395(3) 8_565 ?
C8 C9 1.499(5) . ?
C8 H8A 0.97(3) . ?
C8 H8B 0.9900(11) . ?
C19A H19A 0.9500 . ?
C19A C4 1.914(5) 8_565 ?
C19A C20A 1.374(4) . ?
C4 H4 1.0000 . ?
C20A H20A 0.9500 . ?
C20A C21 1.352(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C21 C21 1.928(9) 8_565 ?
C21 H21 0.9500 . ?
C20B C20B 0.773(8) 8_565 ?
C20B H20B 0.9500 . ?
C20B C19B 1.401(3) . ?
C19B H19B 0.9500 . ?

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 O13 C14 121.78(18) . . ?
C12 N11 C2 128.2(2) . . ?
C12 N11 H11 119(3) . . ?
C2 N11 H11 113(3) . . ?
H5B C5 H5A 109.3 . . ?
C1 C5 H5B 111.4 . . ?
C1 C5 H5A 111.4 . . ?
C1 C5 C4 101.87(19) . . ?
C4 C5 H5B 111.4 . . ?
C4 C5 H5A 111.4 . . ?
C6 O7 C8 115.7(2) . . ?
C6 O7 C8 115.7(2) . 8_565 ?
O13 C12 N11 106.48(19) . . ?
O17 C12 O13 127.3(2) . . ?
O17 C12 N11 126.2(2) . . ?
C2 C1 C5 111.1(2) . . ?
C2 C1 C6 123.2(2) . . ?
C6 C1 C5 125.7(2) . . ?
H3A C3 H3B 109.4 . . ?
C2 C3 H3A 111.6 . . ?
C2 C3 H3B 111.6 . . ?
C2 C3 C4 101.1(2) . . ?
C4 C3 H3A 111.6 . . ?
C4 C3 H3B 111.6 . . ?
N11 C2 C3 124.6(2) . . ?
C1 C2 N11 123.1(2) . . ?
C1 C2 C3 112.3(2) . . ?
O10 C6 O7 122.5(2) . . ?
O10 C6 C1 125.0(2) . . ?
O7 C6 C1 112.4(2) . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
O13 C14 C16 101.56(19) . . ?
O13 C14 C15 109.72(13) . . ?
O13 C14 C15 109.72(13) . 8_565 ?
C15 C14 C16 111.17(15) 8_565 . ?
C15 C14 C16 111.17(15) . . ?
C15 C14 C15 112.9(2) . 8_565 ?
C19A C18 C19A 153.3(4) . 8_565 ?
C19A C18 C4 124.1(3) . . ?
C19A C18 C4 81.8(2) 8_565 . ?
C19A C18 C4 124.1(3) 8_565 8_565 ?
C19A C18 C4 81.8(2) . 8_565 ?
C19B C18 C4 162.0(3) 8_565 8_565 ?
C19B C18 C4 162.0(3) . . ?
C19B C18 C4 119.9(3) 8_565 . ?
C19B C18 C4 119.9(3) . 8_565 ?
C19B C18 C19B 77.5(5) . 8_565 ?
O7 C8 C9 104.5(3) . . ?
O7 C8 H8A 110(2) . . ?
O7 C8 H8B 107(3) . . ?
C9 C8 H8A 114.2(18) . . ?
C9 C8 H8B 112(3) . . ?
H8A C8 H8B 109(2) . . ?
C18 C19A H19A 117.9 . . ?
C18 C19A C4 53.0(2) . 8_565 ?
C18 C19A C20A 124.2(4) . . ?
C4 C19A H19A 64.9 8_565 . ?
C20A C19A H19A 117.9 . . ?
C20A C19A C4 177.2(4) . 8_565 ?
C5 C4 C3 101.8(2) . . ?
C5 C4 H4 110.8 . . ?
C3 C4 H4 110.8 . . ?
C18 C4 C5 111.5(2) . . ?
C18 C4 C3 110.7(3) . . ?
C18 C4 H4 110.8 . . ?
C19A C20A H20A 120.7 . . ?
C21 C20A C19A 118.5(5) . . ?
C21 C20A H20A 120.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C20A C21 C21 129.8(3) . 8_565 ?
C20A C21 H21 115.1 . . ?
C21 C21 H21 115.1 8_565 . ?
C20B C20B H20B 124.8 8_565 . ?
C20B C20B C19B 110.3(2) 8_565 . ?
C19B C20B H20B 124.8 . . ?
C18 C19B C20B 120.7(4) . . ?
C18 C19B H19B 119.6 . . ?
C20B C19B H19B 119.6 . . ?


