# 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. 
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data_191219ysjd1_0m
_database_code_depnum_ccdc_archive 'CCDC 2013513'
loop_
_audit_author_name
_audit_author_address
'Sheng-Jiao Yan'
;School of Chemical Science and Technology, Yunnan University
China
;
_audit_update_record             
;
2020-07-02 deposited with the CCDC.	2020-09-04 downloaded from the CCDC.
;
_audit_creation_date             2019-12-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl O4, C19 H15 F N O4'
_chemical_formula_sum            'C19 H15 Cl F N O8'
_chemical_formula_weight         439.77
_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'
F F 0.0171 0.0103 '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           14
_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                   8.1097(12)
_cell_length_b                   14.3670(19)
_cell_length_c                   16.622(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.194(2)
_cell_angle_gamma                90
_cell_volume                     1916.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4083
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.093
_cell_measurement_theta_min      2.660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0906 before and 0.0323 after correction. The Ratio of minimum to maximum transmission is 0.9218. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11596
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.867
_diffrn_reflns_theta_min         2.660
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3315
_reflns_number_total             4491
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4491
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.034
_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)+(0.0532P)²+0.7741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1193
_refine_special_details          ?
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18),
 C19(H19)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
2.d Idealised tetrahedral OH refined as rotating group:
 O8(H8)
;
_atom_sites_solution_hydrogens   geom
_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 0.10002(6) 0.18853(3) 0.54916(3) 0.04311(15) Uani 1 1 d . . . . .
O1 O 0.0360(2) 0.14959(13) 0.61714(10) 0.0717(5) Uani 1 1 d . . . . .
O2 O -0.0125(2) 0.25742(12) 0.51287(12) 0.0716(5) Uani 1 1 d . . . . .
O3 O 0.1133(3) 0.11725(13) 0.49119(10) 0.0837(6) Uani 1 1 d . . . . .
O4 O 0.2568(2) 0.2270(2) 0.57525(17) 0.1134(9) Uani 1 1 d . . . . .
F1 F 0.86516(18) 0.40170(9) 0.73466(8) 0.0631(4) Uani 1 1 d . . . . .
O5 O 0.5510(2) 0.04404(10) 0.62086(8) 0.0535(4) Uani 1 1 d . . . . .
O6 O 0.41507(18) 0.39280(9) 0.43502(9) 0.0466(3) Uani 1 1 d . . . . .
O7 O 0.5449(3) 0.39474(12) 0.32613(11) 0.0741(6) Uani 1 1 d . . . . .
O8 O 0.4887(2) 0.09350(11) 0.76646(9) 0.0587(4) Uani 1 1 d . . . . .
H8 H 0.480080 0.060474 0.725837 0.088 Uiso 1 1 calc GR . . . .
N1 N 0.71715(18) 0.11895(10) 0.40262(9) 0.0327(3) Uani 1 1 d . . . . .
C1 C 0.7678(3) 0.32544(13) 0.74042(13) 0.0441(5) Uani 1 1 d . . . . .
C2 C 0.7365(2) 0.26772(13) 0.67507(11) 0.0379(4) Uani 1 1 d . . . . .
H2 H 0.779149 0.280910 0.627287 0.045 Uiso 1 1 calc R . . . .
C3 C 0.6387(2) 0.18792(12) 0.68087(10) 0.0341(4) Uani 1 1 d . . . . .
C4 C 0.6021(2) 0.12342(13) 0.61243(11) 0.0361(4) Uani 1 1 d . . . . .
C5 C 0.6247(2) 0.15439(12) 0.52844(10) 0.0316(4) Uani 1 1 d . . . . .
C6 C 0.6962(2) 0.09481(12) 0.48080(11) 0.0346(4) Uani 1 1 d . . . . .
H6 H 0.731802 0.036735 0.501043 0.042 Uiso 1 1 calc R . . . .
C7 C 0.6627(2) 0.20362(12) 0.36855(10) 0.0316(4) Uani 1 1 d . . . . .
C8 C 0.5832(2) 0.26524(12) 0.41847(11) 0.0319(4) Uani 1 1 d . . . . .
C9 C 0.5144(2) 0.35734(13) 0.38666(12) 0.0399(4) Uani 1 1 d . . . . .
C10 C 0.3340(3) 0.48069(15) 0.41034(15) 0.0564(6) Uani 1 1 d . . . . .
H10A H 0.282895 0.477649 0.353962 0.068 Uiso 1 1 calc R . . . .
H10B H 0.414638 0.530958 0.416100 0.068 Uiso 1 1 calc R . . . .
C11 C 0.2049(3) 0.49686(19) 0.4641(2) 0.0753(8) Uani 1 1 d . . . . .
H11A H 0.120588 0.449663 0.454329 0.113 Uiso 1 1 calc GR . . . .
H11B H 0.155193 0.556950 0.452678 0.113 Uiso 1 1 calc GR . . . .
H11C H 0.255516 0.494409 0.519868 0.113 Uiso 1 1 calc GR . . . .
C12 C 0.5664(2) 0.24079(12) 0.49624(10) 0.0326(4) Uani 1 1 d . . . . .
H12 H 0.515754 0.281832 0.528392 0.039 Uiso 1 1 calc R . . . .
C13 C 0.6867(2) 0.21996(14) 0.28787(12) 0.0421(4) Uani 1 1 d . . . . .
H13 H 0.652408 0.276270 0.263425 0.051 Uiso 1 1 calc R . . . .
C14 C 0.7592(3) 0.15517(16) 0.24466(13) 0.0502(5) Uani 1 1 d . . . . .
H14 H 0.772035 0.166799 0.190856 0.060 Uiso 1 1 calc R . . . .
C15 C 0.8143(3) 0.07135(15) 0.28111(13) 0.0498(5) Uani 1 1 d . . . . .
H15 H 0.864798 0.027060 0.251919 0.060 Uiso 1 1 calc R . . . .
C16 C 0.7940(3) 0.05478(13) 0.35858(12) 0.0425(4) Uani 1 1 d . . . . .
H16 H 0.832478 -0.000868 0.382990 0.051 Uiso 1 1 calc R . . . .
C17 C 0.5798(2) 0.16928(14) 0.75476(11) 0.0408(4) Uani 1 1 d . . . . .
C18 C 0.6132(3) 0.23118(16) 0.81943(12) 0.0494(5) Uani 1 1 d . . . . .
H18 H 0.571562 0.219421 0.867736 0.059 Uiso 1 1 calc R . . . .
C19 C 0.7071(3) 0.30931(15) 0.81247(13) 0.0496(5) Uani 1 1 d . . . . .
H19 H 0.729380 0.350741 0.855639 0.060 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 O1 1.4236(16) . ?
Cl1 O2 1.4209(17) . ?
Cl1 O3 1.4207(17) . ?
Cl1 O4 1.398(2) . ?
F1 C1 1.362(2) . ?
O5 C4 1.228(2) . ?
O6 C9 1.319(2) . ?
O6 C10 1.455(2) . ?
O7 C9 1.197(2) . ?
O8 H8 0.8200 . ?
O8 C17 1.345(3) . ?
N1 C6 1.379(2) . ?
N1 C7 1.387(2) . ?
N1 C16 1.380(2) . ?
C1 C2 1.361(3) . ?
C1 C19 1.378(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.405(3) . ?
C3 C4 1.464(3) . ?
C3 C17 1.405(2) . ?
C4 C5 1.501(2) . ?
C5 C6 1.352(2) . ?
C5 C12 1.407(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.428(2) . ?
C7 C13 1.402(3) . ?
C8 C9 1.503(2) . ?
C8 C12 1.365(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.488(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.360(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.393(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.342(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.392(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.370(3) . ?
C19 H19 0.9300 . ?

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
O2 Cl1 O1 109.03(10) . . ?
O3 Cl1 O1 109.07(12) . . ?
O3 Cl1 O2 108.68(12) . . ?
O4 Cl1 O1 109.14(15) . . ?
O4 Cl1 O2 110.89(16) . . ?
O4 Cl1 O3 110.00(15) . . ?
C9 O6 C10 117.01(16) . . ?
C17 O8 H8 109.5 . . ?
C6 N1 C7 122.04(15) . . ?
C6 N1 C16 117.23(15) . . ?
C16 N1 C7 120.73(15) . . ?
F1 C1 C19 118.62(18) . . ?
C2 C1 F1 118.56(19) . . ?
C2 C1 C19 122.8(2) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.03(18) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 121.13(16) . . ?
C2 C3 C17 118.73(17) . . ?
C17 C3 C4 120.12(17) . . ?
O5 C4 C3 122.24(17) . . ?
O5 C4 C5 117.98(16) . . ?
C3 C4 C5 119.78(16) . . ?
C6 C5 C4 118.47(16) . . ?
C6 C5 C12 119.01(16) . . ?
C12 C5 C4 122.43(15) . . ?
N1 C6 H6 119.5 . . ?
C5 C6 N1 120.91(16) . . ?
C5 C6 H6 119.5 . . ?
N1 C7 C8 116.75(15) . . ?
N1 C7 C13 117.23(16) . . ?
C13 C7 C8 125.99(16) . . ?
C7 C8 C9 121.14(15) . . ?
C12 C8 C7 120.33(16) . . ?
C12 C8 C9 118.53(16) . . ?
O6 C9 C8 110.75(15) . . ?
O7 C9 O6 123.78(18) . . ?
O7 C9 C8 125.47(18) . . ?
O6 C10 H10A 110.3 . . ?
O6 C10 H10B 110.3 . . ?
O6 C10 C11 107.1(2) . . ?
H10A C10 H10B 108.5 . . ?
C11 C10 H10A 110.3 . . ?
C11 C10 H10B 110.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C12 H12 119.5 . . ?
C8 C12 C5 120.93(16) . . ?
C8 C12 H12 119.5 . . ?
C7 C13 H13 119.3 . . ?
C14 C13 C7 121.35(19) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.87(19) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.69(19) . . ?
C16 C15 H15 120.2 . . ?
N1 C16 H16 119.4 . . ?
C15 C16 N1 121.10(19) . . ?
C15 C16 H16 119.4 . . ?
O8 C17 C3 122.85(18) . . ?
O8 C17 C18 117.12(18) . . ?
C18 C17 C3 120.02(19) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.7 . . ?
C1 C19 H19 120.6 . . ?
C18 C19 C1 118.86(19) . . ?
C18 C19 H19 120.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O8 H8 O5 0.82 1.93 2.639(2) 144.5 . yes
C13 H13 O7 0.93 2.24 2.871(3) 124.8 . yes

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
F1 C1 C2 C3 178.84(16) . . . . ?
F1 C1 C19 C18 -178.03(18) . . . . ?
O5 C4 C5 C6 -43.3(3) . . . . ?
O5 C4 C5 C12 133.3(2) . . . . ?
O8 C17 C18 C19 179.16(19) . . . . ?
N1 C7 C8 C9 -177.93(15) . . . . ?
N1 C7 C8 C12 1.2(2) . . . . ?
N1 C7 C13 C14 0.5(3) . . . . ?
C1 C2 C3 C4 -179.71(17) . . . . ?
C1 C2 C3 C17 -1.5(3) . . . . ?
C2 C1 C19 C18 1.1(3) . . . . ?
C2 C3 C4 O5 163.01(19) . . . . ?
C2 C3 C4 C5 -17.8(3) . . . . ?
C2 C3 C17 O8 -178.44(18) . . . . ?
C2 C3 C17 C18 2.5(3) . . . . ?
C3 C4 C5 C6 137.51(18) . . . . ?
C3 C4 C5 C12 -46.0(3) . . . . ?
C3 C17 C18 C19 -1.7(3) . . . . ?
C4 C3 C17 O8 -0.2(3) . . . . ?
C4 C3 C17 C18 -179.30(18) . . . . ?
C4 C5 C6 N1 178.74(16) . . . . ?
C4 C5 C12 C8 -177.37(17) . . . . ?
C6 N1 C7 C8 0.0(2) . . . . ?
C6 N1 C7 C13 -178.46(16) . . . . ?
C6 N1 C16 C15 177.71(18) . . . . ?
C6 C5 C12 C8 -0.9(3) . . . . ?
C7 N1 C6 C5 -1.7(3) . . . . ?
C7 N1 C16 C15 -1.8(3) . . . . ?
C7 C8 C9 O6 165.73(16) . . . . ?
C7 C8 C9 O7 -14.7(3) . . . . ?
C7 C8 C12 C5 -0.8(3) . . . . ?
C7 C13 C14 C15 -1.3(3) . . . . ?
C8 C7 C13 C14 -177.77(19) . . . . ?
C9 O6 C10 C11 168.9(2) . . . . ?
C9 C8 C12 C5 178.36(16) . . . . ?
C10 O6 C9 O7 2.6(3) . . . . ?
C10 O6 C9 C8 -177.80(17) . . . . ?
C12 C5 C6 N1 2.1(3) . . . . ?
C12 C8 C9 O6 -13.4(2) . . . . ?
C12 C8 C9 O7 166.2(2) . . . . ?
C13 C7 C8 C9 0.4(3) . . . . ?
C13 C7 C8 C12 179.52(17) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C14 C15 C16 N1 1.0(3) . . . . ?
C16 N1 C6 C5 178.83(17) . . . . ?
C16 N1 C7 C8 179.47(16) . . . . ?
C16 N1 C7 C13 1.0(2) . . . . ?
C17 C3 C4 O5 -15.2(3) . . . . ?
C17 C3 C4 C5 164.03(17) . . . . ?
C17 C18 C19 C1 0.0(3) . . . . ?
C19 C1 C2 C3 -0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
