# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_MB-MM-444-S
_database_code_depnum_ccdc_archive 'CCDC 2016633'
loop_
_audit_author_name
_audit_author_address
'sharada d'
;PONDICHERRY UNIVERSITY
India
;
_audit_update_record             
;
2020-07-15 deposited with the CCDC.	2020-11-17 downloaded from the CCDC.
;
_audit_creation_date             2020-07-15
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_chemical_formula_moiety         'C16 H18 Cl N O6'
_chemical_formula_sum            'C16 H18 Cl N O6'
_chemical_formula_weight         355.78
_chemical_oxdiff_formula         'C34 H26 N2 O11'
_chemical_oxdiff_usercomment     'COLOURLESS BLOCK, 295K, 0.48 0.3 0.13'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/a 1'
_space_group_name_Hall           '-P 2ybc (z,y,-x)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z
3 -x,-y,-z
4 x-1/2,-y-1/2,z

_symmetry_Int_Tables_number      14
_cell_length_a                   11.0420(5)
_cell_length_b                   8.8933(5)
_cell_length_c                   16.9598(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.377(5)
_cell_angle_gamma                90
_cell_volume                     1658.10(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2833
_cell_measurement_temperature    295
_cell_measurement_theta_max      29.1464
_cell_measurement_theta_min      3.6127
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.4251
_exptl_crystal_description       block
_exptl_crystal_F_000             745.0328
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.13
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11912
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         29.21
_diffrn_reflns_theta_min         3.62
_diffrn_ambient_temperature      295
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9935
_diffrn_measured_fraction_theta_max 0.8706
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -75.00  -46.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  127.0000 -119.0000 29

#__ type_ start__ end____ width___ exp.time_
  2 omega  -87.00  -58.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -178.0000  120.0000 29

#__ type_ start__ end____ width___ exp.time_
  3 omega   -7.00   21.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   57.0000  150.0000 28

#__ type_ start__ end____ width___ exp.time_
  4 omega  -16.00   14.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   57.0000    0.0000 30

#__ type_ start__ end____ width___ exp.time_
  5 omega  -13.00   24.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000 -150.0000 37

#__ type_ start__ end____ width___ exp.time_
  6 omega  -64.00  -35.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -178.0000  -90.0000 29

#__ type_ start__ end____ width___ exp.time_
  7 omega  -80.00  -54.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  147.0000  -88.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega  -15.00   41.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   57.0000 -150.0000 56

#__ type_ start__ end____ width___ exp.time_
  9 omega  -71.00    9.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -77.0000  150.0000 80

#__ type_ start__ end____ width___ exp.time_
 10 omega   19.00   88.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1366   57.0000   90.0000 69
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0003323000
_diffrn_orient_matrix_UB_12      -0.0726909000
_diffrn_orient_matrix_UB_13      -0.0172538000
_diffrn_orient_matrix_UB_21      -0.0142660000
_diffrn_orient_matrix_UB_22      0.0321036000
_diffrn_orient_matrix_UB_23      -0.0379848000
_diffrn_orient_matrix_UB_31      0.0629449000
_diffrn_orient_matrix_UB_32      0.0069272000
_diffrn_orient_matrix_UB_33      -0.0047099000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              0
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              -22
_reflns_number_gt                2609
_reflns_number_total             3917
_reflns_odcompleteness_completeness 99.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.3837
_refine_diff_density_min         -0.4095
_refine_diff_density_rms         0.0771
_refine_ls_d_res_high            0.7282
_refine_ls_d_res_low             5.6284
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0578
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3917
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0582
_refine_ls_restrained_S_all      1.0578
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0856P)²+0.5350P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1493
_refine_ls_wR_factor_ref         0.1771
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b), C14(H14a,H14b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C2(H2)
2.d Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C16(H16a,H16b,H16c), C15(H15a,H15b,H15c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
Cl1 Cl 0.52682(6) 0.32422(9) 0.41124(4) 0.0623(3) Uani 1.000000 .
C5 C 0.42071(19) 0.1705(3) 0.61574(14) 0.0389(5) Uani 1.000000 .
O1 O 0.26574(15) -0.0129(2) 0.63898(10) 0.0476(4) Uani 1.000000 .
C6 C 0.4819(2) 0.2497(3) 0.56091(14) 0.0408(5) Uani 1.000000 .
H6 H 0.5429(2) 0.3174(3) 0.57798(14) 0.0490(6) Uiso 1.000000 R
O5 O 0.13020(16) -0.0497(2) 0.79525(12) 0.0533(5) Uani 1.000000 .
C7 C 0.44720(19) 0.1861(3) 0.70436(14) 0.0396(5) Uani 1.000000 .
H7 H 0.52931(19) 0.2253(3) 0.71855(14) 0.0475(6) Uiso 1.000000 R
N1 N 0.35555(17) 0.2705(2) 0.74425(12) 0.0429(5) Uani 1.000000 .
O3 O 0.39896(19) -0.0116(3) 0.87831(11) 0.0689(6) Uani 1.000000 .
O6 O 0.25473(19) -0.2308(2) 0.75797(14) 0.0694(6) Uani 1.000000 .
C4 C 0.3302(2) 0.0693(3) 0.58766(14) 0.0414(5) Uani 1.000000 .
C1 C 0.4512(2) 0.2270(3) 0.48072(14) 0.0447(6) Uani 1.000000 .
C9 C 0.2914(2) 0.0224(3) 0.72047(14) 0.0408(5) Uani 1.000000 .
C13 C 0.4635(2) 0.0327(3) 0.83038(15) 0.0470(6) Uani 1.000000 .
C3 C 0.3012(2) 0.0468(3) 0.50788(16) 0.0506(6) Uani 1.000000 .
H3 H 0.2414(2) -0.0223(3) 0.49035(16) 0.0607(8) Uiso 1.000000 R
O4 O 0.57452(18) 0.0847(3) 0.84720(11) 0.0671(6) Uani 1.000000 .
C10 C 0.2252(2) -0.1014(3) 0.76138(15) 0.0455(6) Uani 1.000000 .
C2 C 0.3613(2) 0.1276(3) 0.45407(15) 0.0504(6) Uani 1.000000 .
H2 H 0.3411(2) 0.1147(3) 0.40001(15) 0.0604(7) Uiso 1.000000 R
C8 C 0.4297(2) 0.0329(3) 0.74197(14) 0.0415(5) Uani 1.000000 .
H8 H 0.4730(2) -0.0461(3) 0.71573(14) 0.0498(6) Uiso 1.000000 R
C12 C -0.0093(4) -0.0815(5) 0.8913(2) 0.0910(12) Uani 1.000000 .
H12a H -0.060(2) -0.006(2) 0.8649(4) 0.1366(18) Uiso 1.000000 GR
H12b H -0.059(2) -0.1523(8) 0.9165(13) 0.1366(18) Uiso 1.000000 GR
H12c H 0.0469(4) -0.035(3) 0.9305(10) 0.1366(18) Uiso 1.000000 GR
C11 C 0.0584(3) -0.1601(3) 0.8332(2) 0.0663(8) Uani 1.000000 .
H11a H 0.0024(3) -0.2096(3) 0.7940(2) 0.0796(10) Uiso 1.000000 R
H11b H 0.1112(3) -0.2357(3) 0.8594(2) 0.0796(10) Uiso 1.000000 R
C16 C 0.3110(3) 0.4084(3) 0.70519(18) 0.0536(7) Uani 1.000000 .
H16a H 0.3776(4) 0.4768(9) 0.7018(11) 0.0804(10) Uiso 1.000000 GR
H16b H 0.2751(16) 0.3853(4) 0.6529(5) 0.0804(10) Uiso 1.000000 GR
H16c H 0.2511(13) 0.4538(12) 0.7351(6) 0.0804(10) Uiso 1.000000 GR
C14 C 0.6174(4) 0.0990(6) 0.9310(2) 0.1003(15) Uani 1.000000 .
H14a H 0.5517(4) 0.1337(6) 0.9605(2) 0.1204(18) Uiso 1.000000 R
H14b H 0.6443(4) 0.0019(6) 0.9519(2) 0.1204(18) Uiso 1.000000 R
C15 C 0.7165(4) 0.2044(6) 0.9396(2) 0.1020(14) Uani 1.000000 .
H15a H 0.7794(14) 0.173(2) 0.9079(16) 0.153(2) Uiso 1.000000 GR
H15b H 0.6879(8) 0.3021(10) 0.9225(19) 0.153(2) Uiso 1.000000 GR
H15c H 0.748(2) 0.209(3) 0.9942(4) 0.153(2) Uiso 1.000000 GR
O2 O 0.24787(14) 0.16625(18) 0.73627(11) 0.0471(4) Uani 1.000000 .


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 C1 1.737(2) . ?
C5 C6 1.391(3) . ?
C5 C7 1.511(3) . ?
C5 C4 1.395(3) . ?
O1 C4 1.384(3) . ?
O1 C9 1.420(3) . ?
C6 C1 1.385(3) . ?
O5 C10 1.324(3) . ?
O5 C11 1.449(3) . ?
C7 N1 1.474(3) . ?
C7 C8 1.525(3) . ?
N1 C16 1.457(3) . ?
N1 O2 1.504(2) . ?
O3 C13 1.197(3) . ?
O6 C10 1.199(3) . ?
C4 C3 1.375(3) . ?
C1 C2 1.374(4) . ?
C9 C10 1.524(3) . ?
C9 C8 1.539(3) . ?
C9 O2 1.402(3) . ?
C13 O4 1.316(3) . ?
C13 C8 1.511(3) . ?
C3 C2 1.380(4) . ?
O4 C14 1.460(4) . ?
C12 C11 1.469(5) . ?
C14 C15 1.438(5) . ?

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
C7 C5 C6 123.9(2) . . ?
C4 C5 C6 118.4(2) . . ?
C4 C5 C7 117.7(2) . . ?
C9 O1 C4 115.35(17) . . ?
C1 C6 C5 119.6(2) . . ?
C11 O5 C10 116.5(2) . . ?
N1 C7 C5 115.23(18) . . ?
C8 C7 C5 108.28(19) . . ?
C8 C7 N1 98.26(17) . . ?
C16 N1 C7 115.89(19) . . ?
O2 N1 C7 102.47(16) . . ?
O2 N1 C16 104.34(18) . . ?
O1 C4 C5 121.3(2) . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 O1 117.1(2) . . ?
C6 C1 Cl1 120.33(19) . . ?
C2 C1 Cl1 118.4(2) . . ?
C2 C1 C6 121.3(2) . . ?
C10 C9 O1 102.88(18) . . ?
C8 C9 O1 110.33(18) . . ?
C8 C9 C10 116.36(19) . . ?
O2 C9 O1 110.30(19) . . ?
O2 C9 C10 112.58(18) . . ?
O2 C9 C8 104.49(18) . . ?
O4 C13 O3 124.8(2) . . ?
C8 C13 O3 124.6(2) . . ?
C8 C13 O4 110.7(2) . . ?
C2 C3 C4 119.5(2) . . ?
C14 O4 C13 116.9(2) . . ?
O6 C10 O5 125.7(2) . . ?
C9 C10 O5 112.4(2) . . ?
C9 C10 O6 121.8(2) . . ?
C3 C2 C1 119.7(2) . . ?
C9 C8 C7 96.70(17) . . ?
C13 C8 C7 112.8(2) . . ?
C13 C8 C9 112.46(19) . . ?
C12 C11 O5 108.1(3) . . ?
C15 C14 O4 109.3(3) . . ?
C9 O2 N1 107.29(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
