# Electronic Supplementary Material (ESI) for Green 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_6_2
_database_code_depnum_ccdc_archive 'CCDC 2012568'
_audit_update_record             
;
2020-06-27 deposited with the CCDC.	2020-10-20 downloaded from the CCDC.
;
_audit_creation_date             2020-06-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C16 H14 Cl N O2), 0.5(H4 O2)'
_chemical_formula_sum            'C32 H30 Cl2 N2 O5'
_chemical_formula_weight         593.48
_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'
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'

_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   16.8614(16)
_cell_length_b                   19.0598(14)
_cell_length_c                   8.8881(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.357(8)
_cell_angle_gamma                90
_cell_volume                     2779.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2104
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      27.1000
_cell_measurement_theta_min      2.4920
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1124
_diffrn_reflns_av_unetI/netI     0.1305
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7169
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.613
_diffrn_reflns_theta_min         2.137
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  29.00   1.00    5.00    --  -11.59 -99.00-180.00   43
  2  ω    -46.00  58.00   1.00    5.00    --  -11.59  19.00-150.00  104
  3  ω     -1.00  51.00   1.00    5.00    --   11.74 -99.00   0.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0350772000
_diffrn_orient_matrix_UB_12      0.0186173000
_diffrn_orient_matrix_UB_13      -0.0395692000
_diffrn_orient_matrix_UB_21      -0.0194422000
_diffrn_orient_matrix_UB_22      -0.0321549000
_diffrn_orient_matrix_UB_23      -0.0263819000
_diffrn_orient_matrix_UB_31      -0.0161863000
_diffrn_orient_matrix_UB_32      -0.0016745000
_diffrn_orient_matrix_UB_33      0.0668521000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2140
_reflns_number_total             3264
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0873
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1152P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2041
_refine_ls_wR_factor_ref         0.2387
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Others
 Fixed Sof: H3A(0.5) H3B(0.5)
3.a Free rotating group:
 O3(H3A,H3B)
3.b Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C15(H15), C14(H14), C12(H12), C2(H2), C5(H5), C13(H13), C4(H4)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Cl1 Cl 0.62383(6) 1.00248(4) 0.30487(10) 0.0366(3) Uani 1 1 d . . . . .
O1 O 0.59398(14) 0.66740(12) 0.4669(2) 0.0217(5) Uani 1 1 d . . . . .
H1 H 0.563196 0.634851 0.433159 0.033 Uiso 1 1 calc R U . . .
O2 O 0.58981(15) 0.55883(11) 0.6588(2) 0.0262(6) Uani 1 1 d . . . . .
O3 O 0.500000 0.44070(16) 0.750000 0.0262(8) Uani 1 2 d GS T P . .
H3A H 0.529064 0.472207 0.721422 0.039 Uiso 0.5 1 d G U P . .
H3B H 0.462207 0.463281 0.777468 0.039 Uiso 0.5 1 d G U P . .
N1 N 0.62286(16) 0.62669(13) 0.8749(3) 0.0194(6) Uani 1 1 d . . . . .
C1 C 0.7137(2) 0.83486(16) 0.5563(3) 0.0188(7) Uani 1 1 d . . . . .
H1A H 0.764283 0.813597 0.590636 0.023 Uiso 1 1 calc R U . . .
C7 C 0.65294(18) 0.73819(15) 0.6883(3) 0.0157(6) Uani 1 1 d . . . . .
H7 H 0.706838 0.718046 0.692011 0.019 Uiso 1 1 calc R U . . .
C15 C 0.65588(19) 0.81739(17) 0.9222(3) 0.0201(7) Uani 1 1 d . . . . .
H15 H 0.668243 0.855485 0.866317 0.024 Uiso 1 1 calc R U . . .
C11 C 0.62977(18) 0.69485(16) 0.9410(3) 0.0171(6) Uani 1 1 d . . . . .
C16 C 0.64630(17) 0.75156(16) 0.8536(3) 0.0166(6) Uani 1 1 d . . . . .
C6 C 0.64495(19) 0.80444(15) 0.5924(3) 0.0161(6) Uani 1 1 d . . . . .
C8 C 0.58872(18) 0.68276(16) 0.6198(3) 0.0168(6) Uani 1 1 d . . . . .
H8 H 0.534496 0.701895 0.617341 0.020 Uiso 1 1 calc R U . . .
C9 C 0.60121(18) 0.61687(17) 0.7198(3) 0.0190(7) Uani 1 1 d . . . . .
C14 C 0.6474(2) 0.82762(18) 1.0727(3) 0.0217(7) Uani 1 1 d . . . . .
H14 H 0.655233 0.871924 1.117485 0.026 Uiso 1 1 calc R U . . .
C12 C 0.61907(19) 0.70534(17) 1.0912(3) 0.0205(7) Uani 1 1 d . . . . .
H12 H 0.606447 0.667550 1.147604 0.025 Uiso 1 1 calc R U . . .
C2 C 0.7080(2) 0.89602(17) 0.4704(3) 0.0228(7) Uani 1 1 d . . . . .
H2 H 0.754189 0.915715 0.447179 0.027 Uiso 1 1 calc R U . . .
C5 C 0.5700(2) 0.83853(17) 0.5425(3) 0.0231(7) Uani 1 1 d . . . . .
H5 H 0.523827 0.819984 0.568122 0.028 Uiso 1 1 calc R U . . .
C13 C 0.62720(19) 0.77149(18) 1.1554(3) 0.0215(7) Uani 1 1 d . . . . .
H13 H 0.619125 0.778435 1.254304 0.026 Uiso 1 1 calc R U . . .
C4 C 0.5635(2) 0.89973(17) 0.4553(3) 0.0252(7) Uani 1 1 d . . . . .
H4 H 0.513314 0.921771 0.421536 0.030 Uiso 1 1 calc R U . . .
C3 C 0.6328(2) 0.92732(17) 0.4196(3) 0.0242(7) Uani 1 1 d . . . . .
C10 C 0.6336(2) 0.56469(18) 0.9742(4) 0.0302(8) Uani 1 1 d . . . . .
H10A H 0.672261 0.574835 1.069289 0.045 Uiso 1 1 calc R U . . .
H10B H 0.653394 0.526506 0.922616 0.045 Uiso 1 1 calc R U . . .
H10C H 0.582321 0.551999 0.995925 0.045 Uiso 1 1 calc R U . . .


_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 1.745(3) . ?
O1 H1 0.8200 . ?
O1 C8 1.413(3) . ?
O2 C9 1.228(4) . ?
O3 H3A 0.8501 . ?
O3 H3A 0.85(11) 2_656 ?
O3 H3B 0.85(9) 2_656 ?
O3 H3B 0.8501 . ?
N1 C11 1.419(4) . ?
N1 C9 1.355(4) . ?
N1 C10 1.461(4) . ?
C1 H1A 0.9300 . ?
C1 C6 1.398(4) . ?
C1 C2 1.384(4) . ?
C7 H7 0.9800 . ?
C7 C16 1.521(4) . ?
C7 C6 1.512(4) . ?
C7 C8 1.535(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.388(4) . ?
C15 C14 1.392(4) . ?
C11 C16 1.396(4) . ?
C11 C12 1.402(4) . ?
C6 C5 1.399(4) . ?
C8 H8 0.9800 . ?
C8 C9 1.525(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.384(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.391(4) . ?
C13 H13 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.384(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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
C8 O1 H1 109.5 . . ?
H3A O3 H3A 90.1 . 2_656 ?
H3A O3 H3B 15.1 . 2_656 ?
H3A O3 H3B 104.5 . . ?
H3A O3 H3B 104.5 2_656 2_656 ?
H3B O3 H3A 15.1 . 2_656 ?
H3B O3 H3B 119.2 . 2_656 ?
C11 N1 C10 120.2(2) . . ?
C9 N1 C11 121.6(2) . . ?
C9 N1 C10 118.0(3) . . ?
C6 C1 H1A 119.3 . . ?
C2 C1 H1A 119.3 . . ?
C2 C1 C6 121.3(3) . . ?
C16 C7 H7 107.9 . . ?
C16 C7 C8 107.2(2) . . ?
C6 C7 H7 107.9 . . ?
C6 C7 C16 112.8(2) . . ?
C6 C7 C8 112.9(2) . . ?
C8 C7 H7 107.9 . . ?
C16 C15 H15 119.3 . . ?
C16 C15 C14 121.4(3) . . ?
C14 C15 H15 119.3 . . ?
C16 C11 N1 119.1(2) . . ?
C16 C11 C12 120.3(3) . . ?
C12 C11 N1 120.5(3) . . ?
C15 C16 C7 123.3(3) . . ?
C15 C16 C11 118.3(3) . . ?
C11 C16 C7 118.4(3) . . ?
C1 C6 C7 120.3(3) . . ?
C1 C6 C5 118.1(3) . . ?
C5 C6 C7 121.5(3) . . ?
O1 C8 C7 109.2(2) . . ?
O1 C8 H8 108.8 . . ?
O1 C8 C9 111.1(2) . . ?
C7 C8 H8 108.8 . . ?
C9 C8 C7 110.2(2) . . ?
C9 C8 H8 108.8 . . ?
O2 C9 N1 123.5(3) . . ?
O2 C9 C8 119.9(3) . . ?
N1 C9 C8 116.6(3) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 C15 119.6(3) . . ?
C13 C14 H14 120.2 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2 120.5 . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 C14 120.1(3) . . ?
C12 C13 H13 120.0 . . ?
C5 C4 H4 120.5 . . ?
C3 C4 C5 119.0(3) . . ?
C3 C4 H4 120.5 . . ?
C2 C3 Cl1 119.7(3) . . ?
C2 C3 C4 121.5(3) . . ?
C4 C3 Cl1 118.8(3) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C8 C9 O2 -21.6(4) . . . . ?
O1 C8 C9 N1 160.0(3) . . . . ?
N1 C11 C16 C7 2.4(4) . . . . ?
N1 C11 C16 C15 -177.6(3) . . . . ?
N1 C11 C12 C13 178.9(3) . . . . ?
C1 C6 C5 C4 2.0(4) . . . . ?
C1 C2 C3 Cl1 -177.5(2) . . . . ?
C1 C2 C3 C4 1.3(4) . . . . ?
C7 C6 C5 C4 179.5(3) . . . . ?
C7 C8 C9 O2 -142.7(3) . . . . ?
C7 C8 C9 N1 38.9(3) . . . . ?
C15 C14 C13 C12 2.8(5) . . . . ?
C11 N1 C9 O2 -175.4(3) . . . . ?
C11 N1 C9 C8 2.9(4) . . . . ?
C11 C12 C13 C14 -1.1(5) . . . . ?
C16 C7 C6 C1 105.0(3) . . . . ?
C16 C7 C6 C5 -72.4(3) . . . . ?
C16 C7 C8 O1 -178.6(2) . . . . ?
C16 C7 C8 C9 -56.3(3) . . . . ?
C16 C15 C14 C13 -1.4(5) . . . . ?
C16 C11 C12 C13 -1.9(5) . . . . ?
C6 C1 C2 C3 0.0(4) . . . . ?
C6 C7 C16 C15 -17.7(4) . . . . ?
C6 C7 C16 C11 162.3(3) . . . . ?
C6 C7 C8 O1 56.5(3) . . . . ?
C6 C7 C8 C9 178.8(2) . . . . ?
C6 C5 C4 C3 -0.8(4) . . . . ?
C8 C7 C16 C15 -142.6(3) . . . . ?
C8 C7 C16 C11 37.5(4) . . . . ?
C8 C7 C6 C1 -133.2(3) . . . . ?
C8 C7 C6 C5 49.3(3) . . . . ?
C9 N1 C11 C16 -25.3(4) . . . . ?
C9 N1 C11 C12 153.8(3) . . . . ?
C14 C15 C16 C7 178.4(3) . . . . ?
C14 C15 C16 C11 -1.6(4) . . . . ?
C12 C11 C16 C7 -176.8(3) . . . . ?
C12 C11 C16 C15 3.2(4) . . . . ?
C2 C1 C6 C7 -179.1(3) . . . . ?
C2 C1 C6 C5 -1.6(4) . . . . ?
C5 C4 C3 Cl1 177.9(2) . . . . ?
C5 C4 C3 C2 -0.9(5) . . . . ?
C10 N1 C11 C16 158.9(3) . . . . ?
C10 N1 C11 C12 -21.9(4) . . . . ?
C10 N1 C9 O2 0.4(5) . . . . ?
C10 N1 C9 C8 178.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.809
_oxdiff_exptl_absorpt_empirical_full_min 0.569
