# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_barbas34
_database_code_depnum_ccdc_archive 'CCDC 1475321'
_audit_update_record             
;
2016-04-20 deposited with the CCDC.
2018-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H23 Cl N2 O5'
_chemical_formula_weight         406.85

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   29.349(2)
_cell_length_b                   11.9764(9)
_cell_length_c                   11.5790(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4070.0(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4340
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      17.22

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1712
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9287
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            11636
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         17.24
_reflns_number_total             1231
_reflns_number_gt                1099
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.1000P)²+16.4000P] 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_number_reflns         1231
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1755
_refine_ls_wR_factor_gt          0.1718
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0.200
_refine_ls_shift/su_mean         0.021

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 0.54060(6) 0.97854(17) 0.63983(16) 0.0385(9) Uani 1 1 d . . .
O1 O 0.8831(2) 0.8067(7) 0.4049(6) 0.053(2) Uani 1 1 d . . .
O2 O 0.70233(19) 0.6179(5) 0.0949(4) 0.0311(15) Uani 1 1 d . . .
O3 O 0.75491(18) 0.7442(5) 0.1366(4) 0.0236(15) Uani 1 1 d . . .
O4 O 0.8931(2) 0.7217(5) 0.5800(7) 0.074(3) Uani 1 1 d . . .
O5 O 0.8297(2) 0.5567(5) 0.6173(6) 0.056(2) Uani 1 1 d . . .
N1 N 0.7002(2) 0.6700(6) 0.3665(5) 0.0223(18) Uani 1 1 d . . .
N2 N 0.8339(3) 0.6777(7) 0.4586(6) 0.0296(19) Uani 1 1 d . . .
C1 C 0.6404(3) 0.7811(6) 0.5280(9) 0.024(2) Uani 1 1 d . . .
H1A H 0.6603 0.7266 0.5599 0.029 Uiso 1 1 calc R . .
C2 C 0.6090(3) 0.8336(8) 0.5978(7) 0.027(2) Uani 1 1 d . . .
H2A H 0.6070 0.8155 0.6775 0.033 Uiso 1 1 calc R . .
C3 C 0.5803(3) 0.9133(7) 0.5499(9) 0.023(2) Uani 1 1 d . . .
C4 C 0.5832(3) 0.9413(6) 0.4363(9) 0.025(2) Uani 1 1 d . . .
H4A H 0.5635 0.9968 0.4053 0.031 Uiso 1 1 calc R . .
C5 C 0.6148(3) 0.8888(8) 0.3658(7) 0.026(2) Uani 1 1 d . . .
H5A H 0.6169 0.9085 0.2864 0.031 Uiso 1 1 calc R . .
C6 C 0.6434(3) 0.8072(7) 0.4115(9) 0.021(2) Uani 1 1 d . . .
C7 C 0.6755(3) 0.7507(8) 0.3326(7) 0.023(2) Uani 1 1 d . . .
H7A H 0.6777 0.7751 0.2548 0.028 Uiso 1 1 calc R . .
C8 C 0.6784(3) 0.5293(7) 0.1532(7) 0.037(2) Uani 1 1 d . . .
H8A H 0.6744 0.4642 0.1015 0.044 Uiso 1 1 calc R . .
H8B H 0.6480 0.5549 0.1791 0.044 Uiso 1 1 calc R . .
C9 C 0.7081(2) 0.4993(6) 0.2560(7) 0.030(2) Uani 1 1 d . . .
H9A H 0.7313 0.4428 0.2348 0.036 Uiso 1 1 calc R . .
H9B H 0.6896 0.4706 0.3210 0.036 Uiso 1 1 calc R . .
C10 C 0.7302(3) 0.6106(6) 0.2861(7) 0.019(2) Uani 1 1 d . . .
C11 C 0.7327(3) 0.6668(8) 0.1680(7) 0.019(2) Uani 1 1 d . . .
C12 C 0.8042(3) 0.7057(6) 0.3588(7) 0.025(2) Uani 1 1 d . . .
H12A H 0.8225 0.7255 0.2900 0.030 Uiso 1 1 calc R . .
H12B H 0.7834 0.7683 0.3775 0.030 Uiso 1 1 calc R . .
C13 C 0.7776(3) 0.5971(6) 0.3395(6) 0.019(2) Uani 1 1 d . . .
H13A H 0.7961 0.5475 0.2881 0.023 Uiso 1 1 calc R . .
C14 C 0.7759(3) 0.5445(6) 0.4598(7) 0.031(2) Uani 1 1 d . . .
H14A H 0.7471 0.5644 0.4994 0.037 Uiso 1 1 calc R . .
H14B H 0.7779 0.4621 0.4544 0.037 Uiso 1 1 calc R . .
C15 C 0.8153(3) 0.5897(9) 0.5234(10) 0.040(3) Uani 1 1 d . . .
C16 C 0.8705(4) 0.7359(11) 0.4872(14) 0.067(4) Uani 1 1 d . . .
C17 C 0.9288(4) 0.8566(9) 0.4149(8) 0.070(3) Uani 1 1 d . . .
C18 C 0.9324(3) 0.9379(7) 0.5200(8) 0.060(3) Uani 1 1 d . . .
H18A H 0.9328 0.8946 0.5918 0.090 Uiso 1 1 calc R . .
H18B H 0.9061 0.9883 0.5202 0.090 Uiso 1 1 calc R . .
H18C H 0.9605 0.9817 0.5139 0.090 Uiso 1 1 calc R . .
C19 C 0.9679(3) 0.7740(7) 0.4150(8) 0.061(3) Uani 1 1 d . . .
H19A H 0.9650 0.7239 0.3486 0.092 Uiso 1 1 calc R . .
H19B H 0.9672 0.7302 0.4865 0.092 Uiso 1 1 calc R . .
H19C H 0.9969 0.8145 0.4101 0.092 Uiso 1 1 calc R . .
C20 C 0.9290(3) 0.9209(9) 0.2992(9) 0.092(4) Uiso 1 1 d . . .
H20A H 0.9278 0.8676 0.2350 0.138 Uiso 1 1 calc R . .
H20B H 0.9570 0.9654 0.2933 0.138 Uiso 1 1 calc R . .
H20C H 0.9025 0.9704 0.2957 0.138 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
Cl1 C3 1.747(8) . ?
O1 C16 1.327(14) . ?
O1 C17 1.474(11) . ?
O2 C11 1.361(9) . ?
O2 C8 1.441(9) . ?
O3 C11 1.190(9) . ?
O4 C16 1.273(14) . ?
O5 C15 1.231(10) . ?
N1 C7 1.270(8) . ?
N1 C10 1.466(9) . ?
N2 C16 1.325(12) . ?
N2 C15 1.404(11) . ?
N2 C12 1.485(9) . ?
C1 C2 1.379(10) . ?
C1 C6 1.387(10) . ?
C2 C3 1.389(10) . ?
C3 C4 1.360(10) . ?
C4 C5 1.387(9) . ?
C5 C6 1.394(10) . ?
C6 C7 1.477(10) . ?
C8 C9 1.519(10) . ?
C9 C10 1.522(10) . ?
C10 C11 1.526(11) . ?
C10 C13 1.532(9) . ?
C12 C13 1.532(10) . ?
C13 C14 1.530(10) . ?
C14 C15 1.474(11) . ?
C17 C19 1.516(12) . ?
C17 C20 1.546(13) . ?
C17 C18 1.561(12) . ?

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
C16 O1 C17 117.1(9) . . ?
C11 O2 C8 110.2(6) . . ?
C7 N1 C10 121.1(7) . . ?
C16 N2 C15 125.2(10) . . ?
C16 N2 C12 123.5(10) . . ?
C15 N2 C12 111.0(8) . . ?
C2 C1 C6 120.6(7) . . ?
C1 C2 C3 119.0(7) . . ?
C4 C3 C2 121.2(7) . . ?
C4 C3 Cl1 120.5(9) . . ?
C2 C3 Cl1 118.3(8) . . ?
C3 C4 C5 120.0(7) . . ?
C4 C5 C6 119.8(7) . . ?
C1 C6 C5 119.3(7) . . ?
C1 C6 C7 122.5(9) . . ?
C5 C6 C7 118.1(9) . . ?
N1 C7 C6 121.5(7) . . ?
O2 C8 C9 105.1(6) . . ?
C8 C9 C10 102.5(6) . . ?
N1 C10 C9 108.4(6) . . ?
N1 C10 C11 112.5(6) . . ?
C9 C10 C11 101.6(6) . . ?
N1 C10 C13 109.9(6) . . ?
C9 C10 C13 112.8(6) . . ?
C11 C10 C13 111.4(6) . . ?
O3 C11 O2 120.3(8) . . ?
O3 C11 C10 130.0(8) . . ?
O2 C11 C10 109.6(8) . . ?
N2 C12 C13 102.8(6) . . ?
C14 C13 C10 112.4(6) . . ?
C14 C13 C12 103.5(6) . . ?
C10 C13 C12 115.6(6) . . ?
C15 C14 C13 106.1(7) . . ?
O5 C15 N2 125.5(9) . . ?
O5 C15 C14 126.3(11) . . ?
N2 C15 C14 108.2(9) . . ?
O4 C16 N2 124.3(14) . . ?
O4 C16 O1 123.1(12) . . ?
N2 C16 O1 112.5(13) . . ?
O1 C17 C19 115.1(8) . . ?
O1 C17 C20 97.9(8) . . ?
C19 C17 C20 108.9(8) . . ?
O1 C17 C18 112.0(7) . . ?
C19 C17 C18 110.8(8) . . ?
C20 C17 C18 111.4(8) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        17.24
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.791
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.064
