# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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 1979517'
loop_
_audit_author_name
_audit_author_address
'Dr Sunil Varughese '
;Senior Scientist CSIR NIIST
India
;
_audit_update_record             
;
2020-01-23 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H28 N2 O6'
_chemical_formula_weight         476.51

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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   31.063(16)
_cell_length_b                   11.549(6)
_cell_length_c                   14.001(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.663(9)
_cell_angle_gamma                90
_cell_volume                     4989(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    4403
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_F_000             2016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.524
_exptl_absorpt_process_details   
;
R. H. Blessing Acta Crystallogr., Sect. A, 1995, 51, 33-58
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      301(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22026
_diffrn_reflns_av_unetI/netI     0.0846
_diffrn_reflns_av_R_equivalents  0.1024
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.071
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             5637
_reflns_number_gt                3141
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0593P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5637
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1346
_refine_ls_wR_factor_gt          0.1281
_refine_ls_goodness_of_fit_ref   0.804
_refine_ls_restrained_S_all      0.804
_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_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
O1 O 0.40834(4) 0.34913(10) 0.09402(9) 0.0387(3) Uani 1 1 d . . . . .
O8 O 0.41165(5) 0.11276(11) 0.16453(9) 0.0505(4) Uani 1 1 d . . . . .
H8 H 0.4199 0.1702 0.1958 0.076 Uiso 1 1 calc R U . . .
O11 O 0.33752(5) 0.01543(12) 0.04398(12) 0.0637(5) Uani 1 1 d . . . . .
O20 O 0.44214(5) 0.29655(12) 0.29344(11) 0.0564(4) Uani 1 1 d . . . . .
O29 O 0.34279(5) 0.43989(15) 0.33501(11) 0.0690(5) Uani 1 1 d . . . . .
O30 O 0.28453(4) 0.36681(12) 0.24370(10) 0.0515(4) Uani 1 1 d . . . . .
N10 N 0.39070(5) 0.00507(13) -0.05593(12) 0.0445(4) Uani 1 1 d . . . . .
N21 N 0.44197(5) 0.49571(13) 0.29619(12) 0.0457(4) Uani 1 1 d . . . . .
C2 C 0.39457(5) 0.40825(15) 0.17426(13) 0.0356(4) Uani 1 1 d . . . . .
C3 C 0.35153(5) 0.35338(14) 0.18705(13) 0.0367(4) Uani 1 1 d . . . . .
C4 C 0.34240(6) 0.27172(15) 0.12196(14) 0.0395(4) Uani 1 1 d . . . . .
H4 H 0.3175 0.2262 0.1171 0.047 Uiso 1 1 calc R U . . .
C5 C 0.37708(6) 0.26183(14) 0.05723(13) 0.0358(4) Uani 1 1 d . . . . .
C6 C 0.36054(7) 0.29095(17) -0.04604(14) 0.0498(5) Uani 1 1 d . . . . .
H6A H 0.3460 0.3644 -0.0483 0.075 Uiso 1 1 calc R U . . .
H6B H 0.3406 0.2321 -0.0718 0.075 Uiso 1 1 calc R U . . .
H6C H 0.3845 0.2947 -0.0835 0.075 Uiso 1 1 calc R U . . .
C7 C 0.40111(6) 0.14393(14) 0.06713(13) 0.0381(4) Uani 1 1 d . . . . .
C9 C 0.37188(7) 0.04737(15) 0.01904(15) 0.0442(5) Uani 1 1 d . . . . .
C12 C 0.37238(8) -0.08648(18) -0.11950(16) 0.0586(6) Uani 1 1 d . . . . .
H12A H 0.3440 -0.1059 -0.1037 0.088 Uiso 1 1 calc R U . . .
H12B H 0.3907 -0.1536 -0.1118 0.088 Uiso 1 1 calc R U . . .
H12C H 0.3704 -0.0604 -0.1850 0.088 Uiso 1 1 calc R U . . .
C13 C 0.43121(6) 0.05751(15) -0.06252(14) 0.0390(4) Uani 1 1 d . . . . .
C14 C 0.43953(6) 0.13988(14) 0.00980(13) 0.0379(4) Uani 1 1 d . . . . .
C15 C 0.47826(6) 0.19830(16) 0.02050(15) 0.0451(5) Uani 1 1 d . . . . .
H15 H 0.4842 0.2529 0.0691 0.054 Uiso 1 1 calc R U . . .
C16 C 0.50847(6) 0.17442(18) -0.04244(16) 0.0525(5) Uani 1 1 d . . . . .
H16 H 0.5348 0.2138 -0.0365 0.063 Uiso 1 1 calc R U . . .
C17 C 0.49964(7) 0.09248(18) -0.11378(16) 0.0525(5) Uani 1 1 d . . . . .
H17 H 0.5202 0.0774 -0.1555 0.063 Uiso 1 1 calc R U . . .
C18 C 0.46083(7) 0.03231(17) -0.12460(15) 0.0475(5) Uani 1 1 d . . . . .
H18 H 0.4551 -0.0233 -0.1724 0.057 Uiso 1 1 calc R U . . .
C19 C 0.42909(6) 0.39029(16) 0.26226(14) 0.0411(4) Uani 1 1 d . . . . .
C22 C 0.47215(8) 0.5139(2) 0.38240(18) 0.0718(7) Uani 1 1 d . . . . .
H22A H 0.4815 0.4403 0.4092 0.108 Uiso 1 1 calc R U . . .
H22B H 0.4580 0.5568 0.4286 0.108 Uiso 1 1 calc R U . . .
H22C H 0.4968 0.5566 0.3662 0.108 Uiso 1 1 calc R U . . .
C23 C 0.42165(6) 0.58517(15) 0.23942(14) 0.0390(4) Uani 1 1 d . . . . .
C24 C 0.42630(6) 0.70279(16) 0.25093(16) 0.0485(5) Uani 1 1 d . . . . .
H24 H 0.4451 0.7339 0.3009 0.058 Uiso 1 1 calc R U . . .
C25 C 0.40191(7) 0.77338(17) 0.18511(17) 0.0528(6) Uani 1 1 d . . . . .
H25 H 0.4039 0.8534 0.1920 0.063 Uiso 1 1 calc R U . . .
C26 C 0.37484(7) 0.72754(17) 0.11002(17) 0.0559(6) Uani 1 1 d . . . . .
H26 H 0.3591 0.7767 0.0664 0.067 Uiso 1 1 calc R U . . .
C27 C 0.37077(6) 0.60865(16) 0.09878(15) 0.0490(5) Uani 1 1 d . . . . .
H27 H 0.3526 0.5776 0.0477 0.059 Uiso 1 1 calc R U . . .
C28 C 0.32645(6) 0.39168(16) 0.26406(15) 0.0439(5) Uani 1 1 d . . . . .
C31 C 0.25153(6) 0.40504(19) 0.30586(17) 0.0538(6) Uani 1 1 d . . . . .
C32 C 0.25213(9) 0.5345(2) 0.3134(3) 0.1026(11) Uani 1 1 d . . . . .
H32A H 0.2787 0.5589 0.3498 0.154 Uiso 1 1 calc R U . . .
H32B H 0.2280 0.5599 0.3452 0.154 Uiso 1 1 calc R U . . .
H32C H 0.2501 0.5677 0.2502 0.154 Uiso 1 1 calc R U . . .
C33 C 0.25911(9) 0.3440(3) 0.4003(2) 0.1004(11) Uani 1 1 d . . . . .
H33A H 0.2857 0.3710 0.4350 0.151 Uiso 1 1 calc R U . . .
H33B H 0.2610 0.2621 0.3896 0.151 Uiso 1 1 calc R U . . .
H33C H 0.2355 0.3596 0.4370 0.151 Uiso 1 1 calc R U . . .
C34 C 0.20967(7) 0.3651(3) 0.2493(2) 0.0830(9) Uani 1 1 d . . . . .
H34A H 0.2095 0.2821 0.2454 0.125 Uiso 1 1 calc R U . . .
H34B H 0.2074 0.3971 0.1856 0.125 Uiso 1 1 calc R U . . .
H34C H 0.1856 0.3907 0.2809 0.125 Uiso 1 1 calc R U . . .
C35 C 0.39388(6) 0.53767(15) 0.16401(14) 0.0370(4) Uani 1 1 d . . . . .


_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 C2 1.422(2) . ?
O1 C5 1.452(2) . ?
O8 C7 1.412(2) . ?
O11 C9 1.218(2) . ?
O20 C19 1.219(2) . ?
O29 C28 1.199(2) . ?
O30 C28 1.332(2) . ?
O30 C31 1.487(2) . ?
N10 C9 1.351(2) . ?
N10 C13 1.409(2) . ?
N10 C12 1.455(2) . ?
N21 C19 1.351(2) . ?
N21 C23 1.408(2) . ?
N21 C22 1.455(3) . ?
C2 C35 1.501(2) . ?
C2 C3 1.509(2) . ?
C2 C19 1.551(3) . ?
C3 C4 1.319(2) . ?
C3 C28 1.470(3) . ?
C4 C5 1.491(2) . ?
C5 C6 1.515(3) . ?
C5 C7 1.551(2) . ?
C7 C14 1.514(3) . ?
C7 C9 1.543(3) . ?
C13 C18 1.368(3) . ?
C13 C14 1.391(3) . ?
C14 C15 1.372(3) . ?
C15 C16 1.388(3) . ?
C16 C17 1.380(3) . ?
C17 C18 1.385(3) . ?
C23 C24 1.374(3) . ?
C23 C35 1.396(3) . ?
C24 C25 1.388(3) . ?
C25 C26 1.374(3) . ?
C26 C27 1.386(3) . ?
C27 C35 1.367(3) . ?
C31 C33 1.493(3) . ?
C31 C32 1.499(3) . ?
C31 C34 1.514(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
C2 O1 C5 111.31(12) . . ?
C28 O30 C31 122.29(16) . . ?
C9 N10 C13 111.46(16) . . ?
C9 N10 C12 124.36(17) . . ?
C13 N10 C12 124.14(15) . . ?
C19 N21 C23 111.59(16) . . ?
C19 N21 C22 123.92(18) . . ?
C23 N21 C22 124.47(17) . . ?
O1 C2 C35 113.86(14) . . ?
O1 C2 C3 104.12(14) . . ?
C35 C2 C3 115.25(14) . . ?
O1 C2 C19 108.64(14) . . ?
C35 C2 C19 102.12(14) . . ?
C3 C2 C19 112.96(15) . . ?
C4 C3 C28 129.20(17) . . ?
C4 C3 C2 109.93(15) . . ?
C28 C3 C2 120.87(16) . . ?
C3 C4 C5 111.23(16) . . ?
O1 C5 C4 103.41(14) . . ?
O1 C5 C6 108.86(15) . . ?
C4 C5 C6 111.97(16) . . ?
O1 C5 C7 106.42(14) . . ?
C4 C5 C7 112.78(14) . . ?
C6 C5 C7 112.74(15) . . ?
O8 C7 C14 113.30(16) . . ?
O8 C7 C9 107.22(14) . . ?
C14 C7 C9 101.92(14) . . ?
O8 C7 C5 111.43(14) . . ?
C14 C7 C5 112.36(14) . . ?
C9 C7 C5 110.04(16) . . ?
O11 C9 N10 125.87(19) . . ?
O11 C9 C7 125.79(17) . . ?
N10 C9 C7 108.34(15) . . ?
C18 C13 C14 121.73(18) . . ?
C18 C13 N10 128.43(18) . . ?
C14 C13 N10 109.75(15) . . ?
C15 C14 C13 120.13(17) . . ?
C15 C14 C7 131.43(18) . . ?
C13 C14 C7 108.40(16) . . ?
C14 C15 C16 118.81(19) . . ?
C17 C16 C15 120.24(19) . . ?
C16 C17 C18 121.39(19) . . ?
C13 C18 C17 117.7(2) . . ?
O20 C19 N21 127.01(19) . . ?
O20 C19 C2 125.03(17) . . ?
N21 C19 C2 107.95(16) . . ?
C24 C23 C35 121.65(18) . . ?
C24 C23 N21 128.72(19) . . ?
C35 C23 N21 109.63(16) . . ?
C23 C24 C25 117.5(2) . . ?
C26 C25 C24 121.36(19) . . ?
C25 C26 C27 120.5(2) . . ?
C35 C27 C26 119.0(2) . . ?
O29 C28 O30 125.94(18) . . ?
O29 C28 C3 122.55(18) . . ?
O30 C28 C3 111.51(17) . . ?
O30 C31 C33 109.24(19) . . ?
O30 C31 C32 109.52(18) . . ?
C33 C31 C32 114.1(3) . . ?
O30 C31 C34 102.23(18) . . ?
C33 C31 C34 110.9(2) . . ?
C32 C31 C34 110.1(2) . . ?
C27 C35 C23 120.01(18) . . ?
C27 C35 C2 131.39(18) . . ?
C23 C35 C2 108.56(16) . . ?

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_BRJ209
_database_code_depnum_ccdc_archive 'CCDC 1979628'
loop_
_audit_author_name
_audit_author_address
'Dr. Eringathodi Suresh'
;Senior Principal Scientist, CSIR CSMCRI
India
;
_audit_update_record             
;
2020-01-23 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ORGANIC
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H32 Cl2 N2 O8'
_chemical_formula_iupac          ?
_chemical_formula_weight         643.49

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.1365(3)
_cell_length_b                   7.2858(2)
_cell_length_c                   19.8596(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.7080(10)
_cell_angle_gamma                90
_cell_volume                     1605.94(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9981
_cell_measurement_theta_min      2.1762
_cell_measurement_theta_max      30.6475
_cell_measurement_temperature    177.(2)

_exptl_crystal_description       BLOCKS
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.227
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.096
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672

_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_type   'MULTI SCAN'
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_absorpt_correction_T_min  0.9440
_exptl_absorpt_correction_T_max  0.9760

_exptl_special_details           
;
;

_diffrn_ambient_temperature      177.(2)

_diffrn_source                   ?
_diffrn_source_type              'MICRO FOCUS TUBE'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            48722
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         33.16
_diffrn_reflns_theta_full        33.16
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30

_refine_special_details          
;
;

_reflns_number_total             6124
_reflns_number_gt                4319
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1404
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_number_reflns         6124
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0597P)²+0.4124P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.283
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Cl Cl 0.1484 0.1585 '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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.33488(12) 0.31173(18) 0.66728(6) 0.0329(3) Uani d . . . 1 . .
H H1 0.3908(15) 0.331(2) 0.6343(8) 0.039(4) Uiso d . . . 1 . .
O O1 -0.08031(8) 0.36671(14) 0.56738(5) 0.0360(2) Uani d . . . 1 . .
Cl Cl1 0.52911(4) 0.27160(7) 0.75703(2) 0.06377(16) Uani d . . . 1 . .
O O2 0.16714(8) 0.52763(12) 0.56084(4) 0.02880(18) Uani d . . . 1 . .
H H2C 0.1306(16) 0.538(3) 0.5219(9) 0.049(5) Uiso d . . . 1 . .
C C2 0.37463(14) 0.27670(18) 0.73452(7) 0.0389(3) Uani d . . . 1 . .
C C3 0.29616(16) 0.24689(18) 0.78336(7) 0.0408(3) Uani d . . . 1 . .
H H3 0.3294(16) 0.222(2) 0.8280(9) 0.040(4) Uiso d . . . 1 . .
O O3 0.44537(14) 0.2990(2) 0.37333(7) 0.0726(4) Uani d . . . 1 . .
O O4 0.44984(9) 0.24952(14) 0.48463(6) 0.0428(2) Uani d . . . 1 . .
C C4 0.17225(15) 0.25210(18) 0.76745(6) 0.0378(3) Uani d . . . 1 . .
H H4 0.1183(17) 0.233(2) 0.8005(9) 0.040(5) Uiso d . . . 1 . .
N N005 0.01293(10) 0.30264(16) 0.67201(5) 0.0329(2) Uani d . . . 1 . .
C C5 0.13233(12) 0.28802(16) 0.70082(6) 0.0300(2) Uani d . . . 1 . .
C C6 0.21238(11) 0.31728(16) 0.65181(5) 0.0269(2) Uani d . . . 1 . .
C C7 0.01041(11) 0.34190(16) 0.60519(6) 0.0277(2) Uani d . . . 1 . .
C C9 0.16210(10) 0.19718(16) 0.53499(6) 0.0260(2) Uani d . . . 1 . .
C C8 0.14175(10) 0.35139(15) 0.58483(5) 0.0243(2) Uani d . . . 1 . .
C C10 0.20778(12) 0.23579(17) 0.47876(6) 0.0310(2) Uani d . . . 1 . .
C C11 0.26111(15) 0.2742(2) 0.42432(7) 0.0394(3) Uani d . . . 1 . .
H H11 0.2156(19) 0.304(3) 0.3811(11) 0.063(6) Uiso d . . . 1 . .
C C12 0.39357(16) 0.2755(2) 0.42363(8) 0.0431(3) Uani d . . . 1 . .
C C13 0.58066(16) 0.2414(3) 0.48883(12) 0.0592(5) Uani d . . . 1 . .
H H13A 0.602(2) 0.137(4) 0.4555(13) 0.085(7) Uiso d . . . 1 . .
H H13B 0.607(2) 0.351(3) 0.4667(11) 0.070(6) Uiso d . . . 1 . .
C C14 0.62268(16) 0.2251(3) 0.56142(13) 0.0606(5) Uani d . . . 1 . .
H H14C 0.702(3) 0.222(3) 0.5660(13) 0.082(8) Uiso d . . . 1 . .
H H14B 0.5885(18) 0.113(3) 0.5841(10) 0.058(5) Uiso d . . . 1 . .
H H14A 0.6011(19) 0.329(3) 0.5884(11) 0.065(6) Uiso d . . . 1 . .
C C15 -0.09469(17) 0.2839(3) 0.70830(9) 0.0483(4) Uani d . . . 1 . .
H H15B -0.094(2) 0.171(4) 0.7251(14) 0.097(9) Uiso d . . . 1 . .
H H15A -0.166(3) 0.309(4) 0.6788(14) 0.103(9) Uiso d . . . 1 . .
H H15C -0.087(2) 0.364(3) 0.7458(13) 0.082(7) Uiso d . . . 1 . .
C C16 0.13298(14) 0.00459(19) 0.55602(7) 0.0366(3) Uani d . . . 1 . .
H H16C 0.1423(16) -0.084(3) 0.5192(9) 0.053(5) Uiso d . . . 1 . .
H H16A 0.1890(17) -0.030(3) 0.5955(10) 0.059(5) Uiso d . . . 1 . .
H H16B 0.0529(16) -0.004(3) 0.5687(9) 0.048(5) Uiso d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.3741(17) ?
C1 C2 . 1.3953(18) ?
C1 H1 . 0.951(17) ?
O1 C7 . 1.2218(15) ?
Cl1 C2 . 1.7420(16) ?
O2 C8 . 1.4063(14) ?
O2 H2C . 0.847(18) ?
C2 C3 . 1.375(2) ?
C3 C4 . 1.391(2) ?
C3 H3 . 0.949(17) ?
O3 C12 . 1.2061(18) ?
O4 C12 . 1.331(2) ?
O4 C13 . 1.454(2) ?
C4 C5 . 1.3857(17) ?
C4 H4 . 0.935(19) ?
N005 C7 . 1.3555(15) ?
N005 C5 . 1.4078(17) ?
N005 C15 . 1.4547(18) ?
C5 C6 . 1.3894(17) ?
C6 C8 . 1.5093(15) ?
C7 C8 . 1.5507(16) ?
C9 C10 . 1.2954(17) ?
C9 C16 . 1.5069(18) ?
C9 C8 . 1.5265(16) ?
C10 C11 . 1.3060(19) ?
C11 C12 . 1.476(2) ?
C11 H11 . 0.98(2) ?
C13 C14 . 1.483(3) ?
C13 H13A . 1.05(3) ?
C13 H13B . 0.97(2) ?
C14 H14C . 0.88(3) ?
C14 H14B . 1.02(2) ?
C14 H14A . 0.97(2) ?
C15 H15B . 0.89(3) ?
C15 H15A . 0.97(3) ?
C15 H15C . 0.94(3) ?
C16 H16C . 0.986(19) ?
C16 H16A . 0.99(2) ?
C16 H16B . 0.948(18) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 116.79(13) ?
C6 C1 H1 . . 122.4(10) ?
C2 C1 H1 . . 120.8(10) ?
C8 O2 H2C . . 107.1(13) ?
C3 C2 C1 . . 122.26(14) ?
C3 C2 Cl1 . . 119.14(10) ?
C1 C2 Cl1 . . 118.59(13) ?
C2 C3 C4 . . 120.77(12) ?
C2 C3 H3 . . 117.8(11) ?
C4 C3 H3 . . 121.4(11) ?
C12 O4 C13 . . 116.92(14) ?
C5 C4 C3 . . 117.17(14) ?
C5 C4 H4 . . 121.6(11) ?
C3 C4 H4 . . 121.2(11) ?
C7 N005 C5 . . 110.91(10) ?
C7 N005 C15 . . 123.58(12) ?
C5 N005 C15 . . 125.49(12) ?
C4 C5 C6 . . 121.60(13) ?
C4 C5 N005 . . 128.36(13) ?
C6 C5 N005 . . 110.03(10) ?
C1 C6 C5 . . 121.40(11) ?
C1 C6 C8 . . 129.65(11) ?
C5 C6 C8 . . 108.95(10) ?
O1 C7 N005 . . 125.63(11) ?
O1 C7 C8 . . 125.68(10) ?
N005 C7 C8 . . 108.69(10) ?
C10 C9 C16 . . 123.35(11) ?
C10 C9 C8 . . 119.27(11) ?
C16 C9 C8 . . 117.31(10) ?
O2 C8 C6 . . 110.13(9) ?
O2 C8 C9 . . 114.06(9) ?
C6 C8 C9 . . 110.85(9) ?
O2 C8 C7 . . 110.44(9) ?
C6 C8 C7 . . 101.39(9) ?
C9 C8 C7 . . 109.25(9) ?
C9 C10 C11 . . 176.08(14) ?
C10 C11 C12 . . 122.12(14) ?
C10 C11 H11 . . 122.2(13) ?
C12 C11 H11 . . 115.7(13) ?
O3 C12 O4 . . 123.55(17) ?
O3 C12 C11 . . 123.69(17) ?
O4 C12 C11 . . 112.75(12) ?
O4 C13 C14 . . 107.09(15) ?
O4 C13 H13A . . 105.8(13) ?
C14 C13 H13A . . 119.0(14) ?
O4 C13 H13B . . 106.0(13) ?
C14 C13 H13B . . 115.1(14) ?
H13A C13 H13B . . 103.(2) ?
C13 C14 H14C . . 109.7(17) ?
C13 C14 H14B . . 113.2(11) ?
H14C C14 H14B . . 109.8(19) ?
C13 C14 H14A . . 113.6(13) ?
H14C C14 H14A . . 105.(2) ?
H14B C14 H14A . . 105.3(18) ?
N005 C15 H15B . . 106.7(18) ?
N005 C15 H15A . . 110.7(17) ?
H15B C15 H15A . . 113.(2) ?
N005 C15 H15C . . 108.0(15) ?
H15B C15 H15C . . 106.(2) ?
H15A C15 H15C . . 112.(2) ?
C9 C16 H16C . . 111.4(11) ?
C9 C16 H16A . . 108.6(12) ?
H16C C16 H16A . . 108.8(15) ?
C9 C16 H16B . . 111.1(11) ?
H16C C16 H16B . . 108.3(15) ?
H16A C16 H16B . . 108.5(15) ?

