# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_17013_lc1940ef1
_audit_block_doi                 10.5517/ccdc.csd.cc1p160y
_database_code_depnum_ccdc_archive 'CCDC 1550279'
_audit_update_record             
;
2017-05-16 deposited with the CCDC.	2020-08-19 downloaded from the CCDC.
;

_audit_creation_date             2017-02-20T13:36:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H24 Cl1 N3 O6'
_chemical_formula_sum            'C23 H24 Cl N3 O6'
_chemical_formula_weight         473.9
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.46480(10)
_cell_length_b                   15.9282(2)
_cell_length_c                   16.6678(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2247.30(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    11023
_cell_measurement_theta_min      5.239
_cell_measurement_theta_max      69.639
_cell_measurement_wavelength     1.5418

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.29
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.84612
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.264
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0704075
_diffrn_orient_matrix_ub_12      0.014925
_diffrn_orient_matrix_ub_13      0.0840178
_diffrn_orient_matrix_ub_21      -0.1643725
_diffrn_orient_matrix_ub_22      0.0129091
_diffrn_orient_matrix_ub_23      -0.0376597
_diffrn_orient_matrix_ub_31      -0.0337639
_diffrn_orient_matrix_ub_32      -0.0947008
_diffrn_orient_matrix_ub_33      0.0080565
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_number            13091
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.31
_diffrn_reflns_theta_max         69.67
_diffrn_reflns_theta_full        69.67
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             4087
_reflns_number_gt                4006
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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)+(0.0374P)²+0.2981P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4087
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0683
_refine_ls_wR_factor_gt          0.0678
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.002(11)
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.034

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Cl01 Cl 0.77625(7) 0.17650(3) -0.00778(2) 0.05620(14) Uani 1 1 d . . .
O002 O 0.74057(11) 0.23898(5) 0.38551(5) 0.0248(2) Uani 1 1 d . . .
O003 O 0.26530(13) 0.17043(7) 0.36059(7) 0.0417(3) Uani 1 1 d . . .
O004 O 0.44837(12) 0.25855(6) 0.30608(6) 0.0290(2) Uani 1 1 d . . .
O005 O 0.93567(14) 0.28570(6) 0.46288(7) 0.0398(3) Uani 1 1 d . . .
N006 N 0.52698(14) 0.14352(7) 0.37088(7) 0.0248(2) Uani 1 1 d . . .
N007 N 0.99000(15) 0.11948(8) 0.50509(7) 0.0304(3) Uani 1 1 d . . .
O008 O 1.32823(18) 0.05535(9) 0.73779(8) 0.0582(4) Uani 1 1 d . . .
C009 C 0.71642(16) 0.16356(8) 0.26020(8) 0.0237(3) Uani 1 1 d . . .
O010 O 1.46664(17) -0.05217(8) 0.70526(9) 0.0594(4) Uani 1 1 d . . .
C011 C 0.78234(17) 0.09121(8) 0.39730(8) 0.0243(3) Uani 1 1 d . . .
H011 H 0.8109 0.0428 0.3619 0.029 Uiso 1 1 calc R . .
C012 C 1.09664(17) 0.05557(8) 0.52073(8) 0.0276(3) Uani 1 1 d . . .
C013 C 0.2451(2) 0.24940(11) 0.20197(9) 0.0422(4) Uani 1 1 d . . .
H01A H 0.177 0.2122 0.2335 0.063 Uiso 1 1 calc R . .
H01B H 0.3201 0.2157 0.1709 0.063 Uiso 1 1 calc R . .
H01C H 0.18 0.2829 0.1654 0.063 Uiso 1 1 calc R . .
C014 C 0.68884(16) 0.15930(8) 0.35020(7) 0.0227(3) Uani 1 1 d . . .
C015 C 0.66771(17) 0.06448(8) 0.46332(9) 0.0283(3) Uani 1 1 d . . .
H01D H 0.689 0.0061 0.4807 0.034 Uiso 1 1 calc R . .
H01E H 0.6758 0.1022 0.5104 0.034 Uiso 1 1 calc R . .
C016 C 1.17578(17) 0.05774(9) 0.59471(9) 0.0290(3) Uani 1 1 d . . .
H016 H 1.1576 0.1023 0.6314 0.035 Uiso 1 1 calc R . .
N017 N 1.36347(17) -0.00084(8) 0.69099(9) 0.0401(3) Uani 1 1 d . . .
C018 C 0.83229(18) 0.22727(9) 0.14324(9) 0.0323(3) Uani 1 1 d . . .
H018 H 0.8987 0.2685 0.1196 0.039 Uiso 1 1 calc R . .
C019 C 0.40039(17) 0.18972(9) 0.34623(8) 0.0277(3) Uani 1 1 d . . .
C020 C 0.81241(17) 0.22430(8) 0.22611(8) 0.0284(3) Uani 1 1 d . . .
H020 H 0.8648 0.264 0.2593 0.034 Uiso 1 1 calc R . .
C021 C 0.87424(17) 0.22894(8) 0.42809(8) 0.0267(3) Uani 1 1 d . . .
C022 C 0.64180(19) 0.10534(9) 0.21121(9) 0.0323(3) Uani 1 1 d . . .
H022 H 0.5778 0.0629 0.2346 0.039 Uiso 1 1 calc R . .
C023 C 0.92995(17) 0.13833(8) 0.42577(8) 0.0273(3) Uani 1 1 d . . .
H023 H 1.0164 0.1321 0.3853 0.033 Uiso 1 1 calc R . .
C024 C 0.50623(17) 0.07139(8) 0.42442(8) 0.0273(3) Uani 1 1 d . . .
H02A H 0.4796 0.0199 0.394 0.033 Uiso 1 1 calc R . .
H02B H 0.4229 0.0821 0.4648 0.033 Uiso 1 1 calc R . .
C025 C 1.12498(18) -0.01144(9) 0.46855(9) 0.0323(3) Uani 1 1 d . . .
H025 H 1.0718 -0.0143 0.4184 0.039 Uiso 1 1 calc R . .
C026 C 0.4413(2) 0.36490(10) 0.20971(10) 0.0378(4) Uani 1 1 d . . .
H02C H 0.4988 0.4021 0.2463 0.057 Uiso 1 1 calc R . .
H02D H 0.3771 0.3987 0.173 0.057 Uiso 1 1 calc R . .
H02E H 0.5167 0.3313 0.1788 0.057 Uiso 1 1 calc R . .
C027 C 1.28041(18) -0.00583(9) 0.61341(9) 0.0321(3) Uani 1 1 d . . .
C028 C 0.33462(18) 0.30715(9) 0.25774(8) 0.0305(3) Uani 1 1 d . . .
C029 C 0.2270(2) 0.35683(11) 0.31291(10) 0.0459(4) Uani 1 1 d . . .
H02F H 0.291 0.3929 0.3477 0.069 Uiso 1 1 calc R . .
H02G H 0.165 0.318 0.3459 0.069 Uiso 1 1 calc R . .
H02H H 0.1556 0.3916 0.2807 0.069 Uiso 1 1 calc R . .
C030 C 1.2314(2) -0.07409(9) 0.49030(10) 0.0377(3) Uani 1 1 d . . .
H030 H 1.2499 -0.1192 0.4543 0.045 Uiso 1 1 calc R . .
C031 C 1.3110(2) -0.07266(9) 0.56252(10) 0.0373(4) Uani 1 1 d . . .
H031 H 1.3836 -0.1156 0.5767 0.045 Uiso 1 1 calc R . .
C032 C 0.6596(2) 0.10846(10) 0.12848(9) 0.0376(4) Uani 1 1 d . . .
H032 H 0.6072 0.0691 0.0949 0.045 Uiso 1 1 calc R . .
C033 C 0.7549(2) 0.16999(9) 0.09611(8) 0.0354(3) Uani 1 1 d . . .
H100 H 1.007(2) 0.1655(12) 0.5317(11) 0.037(5) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Cl01 C033 1.7441(14) . ?
O002 C021 1.3452(17) . ?
O002 C014 1.4659(15) . ?
O003 C019 1.2080(18) . ?
O004 C019 1.3472(17) . ?
O004 C028 1.4749(17) . ?
O005 C021 1.1932(17) . ?
N006 C019 1.3633(18) . ?
N006 C014 1.4350(17) . ?
N006 C024 1.4653(16) . ?
N007 C012 1.3853(18) . ?
N007 C023 1.4480(18) . ?
N007 H100 0.87(2) . ?
O008 N017 1.2241(19) . ?
C009 C020 1.3853(19) . ?
C009 C022 1.388(2) . ?
C009 C014 1.5196(17) . ?
O010 N017 1.2197(18) . ?
C011 C015 1.5277(19) . ?
C011 C023 1.5328(19) . ?
C011 C014 1.5553(18) . ?
C011 H011 1 . ?
C012 C025 1.398(2) . ?
C012 C016 1.404(2) . ?
C013 C028 1.512(2) . ?
C013 H01A 0.98 . ?
C013 H01B 0.98 . ?
C013 H01C 0.98 . ?
C015 C024 1.517(2) . ?
C015 H01D 0.99 . ?
C015 H01E 0.99 . ?
C016 C027 1.381(2) . ?
C016 H016 0.95 . ?
N017 C027 1.474(2) . ?
C018 C033 1.371(2) . ?
C018 C020 1.392(2) . ?
C018 H018 0.95 . ?
C020 H020 0.95 . ?
C021 C023 1.5190(19) . ?
C022 C032 1.388(2) . ?
C022 H022 0.95 . ?
C023 H023 1 . ?
C024 H02A 0.99 . ?
C024 H02B 0.99 . ?
C025 C030 1.393(2) . ?
C025 H025 0.95 . ?
C026 C028 1.517(2) . ?
C026 H02C 0.98 . ?
C026 H02D 0.98 . ?
C026 H02E 0.98 . ?
C027 C031 1.385(2) . ?
C028 C029 1.517(2) . ?
C029 H02F 0.98 . ?
C029 H02G 0.98 . ?
C029 H02H 0.98 . ?
C030 C031 1.379(2) . ?
C030 H030 0.95 . ?
C031 H031 0.95 . ?
C032 C033 1.379(2) . ?
C032 H032 0.95 . ?

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
C021 O002 C014 111.12(10) . . ?
C019 O004 C028 120.11(11) . . ?
C019 N006 C014 125.70(11) . . ?
C019 N006 C024 120.83(11) . . ?
C014 N006 C024 113.46(11) . . ?
C012 N007 C023 123.56(12) . . ?
C012 N007 H100 114.5(12) . . ?
C023 N007 H100 110.5(12) . . ?
C020 C009 C022 119.49(12) . . ?
C020 C009 C014 121.75(12) . . ?
C022 C009 C014 118.76(12) . . ?
C015 C011 C023 115.55(11) . . ?
C015 C011 C014 103.58(11) . . ?
C023 C011 C014 103.28(10) . . ?
C015 C011 H011 111.3 . . ?
C023 C011 H011 111.3 . . ?
C014 C011 H011 111.3 . . ?
N007 C012 C025 123.78(13) . . ?
N007 C012 C016 117.26(13) . . ?
C025 C012 C016 118.92(13) . . ?
C028 C013 H01A 109.5 . . ?
C028 C013 H01B 109.5 . . ?
H01A C013 H01B 109.5 . . ?
C028 C013 H01C 109.5 . . ?
H01A C013 H01C 109.5 . . ?
H01B C013 H01C 109.5 . . ?
N006 C014 O002 109.90(10) . . ?
N006 C014 C009 113.06(11) . . ?
O002 C014 C009 108.17(10) . . ?
N006 C014 C011 104.03(10) . . ?
O002 C014 C011 104.42(10) . . ?
C009 C014 C011 116.82(11) . . ?
C024 C015 C011 104.13(11) . . ?
C024 C015 H01D 110.9 . . ?
C011 C015 H01D 110.9 . . ?
C024 C015 H01E 110.9 . . ?
C011 C015 H01E 110.9 . . ?
H01D C015 H01E 108.9 . . ?
C027 C016 C012 119.10(13) . . ?
C027 C016 H016 120.5 . . ?
C012 C016 H016 120.5 . . ?
O010 N017 O008 122.70(15) . . ?
O010 N017 C027 118.46(14) . . ?
O008 N017 C027 118.83(13) . . ?
C033 C018 C020 119.22(14) . . ?
C033 C018 H018 120.4 . . ?
C020 C018 H018 120.4 . . ?
O003 C019 O004 126.21(13) . . ?
O003 C019 N006 123.17(13) . . ?
O004 C019 N006 110.61(12) . . ?
C009 C020 C018 120.10(13) . . ?
C009 C020 H020 119.9 . . ?
C018 C020 H020 119.9 . . ?
O005 C021 O002 122.20(13) . . ?
O005 C021 C023 126.66(13) . . ?
O002 C021 C023 111.13(11) . . ?
C009 C022 C032 120.75(14) . . ?
C009 C022 H022 119.6 . . ?
C032 C022 H022 119.6 . . ?
N007 C023 C021 106.42(11) . . ?
N007 C023 C011 117.86(12) . . ?
C021 C023 C011 102.71(11) . . ?
N007 C023 H023 109.8 . . ?
C021 C023 H023 109.8 . . ?
C011 C023 H023 109.8 . . ?
N006 C024 C015 102.07(11) . . ?
N006 C024 H02A 111.4 . . ?
C015 C024 H02A 111.4 . . ?
N006 C024 H02B 111.4 . . ?
C015 C024 H02B 111.4 . . ?
H02A C024 H02B 109.2 . . ?
C030 C025 C012 119.76(14) . . ?
C030 C025 H025 120.1 . . ?
C012 C025 H025 120.1 . . ?
C028 C026 H02C 109.5 . . ?
C028 C026 H02D 109.5 . . ?
H02C C026 H02D 109.5 . . ?
C028 C026 H02E 109.5 . . ?
H02C C026 H02E 109.5 . . ?
H02D C026 H02E 109.5 . . ?
C016 C027 C031 123.02(14) . . ?
C016 C027 N017 117.68(13) . . ?
C031 C027 N017 119.30(13) . . ?
O004 C028 C013 110.12(12) . . ?
O004 C028 C029 109.54(12) . . ?
C013 C028 C029 112.90(15) . . ?
O004 C028 C026 102.60(12) . . ?
C013 C028 C026 110.05(13) . . ?
C029 C028 C026 111.14(13) . . ?
C028 C029 H02F 109.5 . . ?
C028 C029 H02G 109.5 . . ?
H02F C029 H02G 109.5 . . ?
C028 C029 H02H 109.5 . . ?
H02F C029 H02H 109.5 . . ?
H02G C029 H02H 109.5 . . ?
C031 C030 C025 122.09(14) . . ?
C031 C030 H030 119 . . ?
C025 C030 H030 119 . . ?
C030 C031 C027 117.12(14) . . ?
C030 C031 H031 121.4 . . ?
C027 C031 H031 121.4 . . ?
C033 C032 C022 118.52(14) . . ?
C033 C032 H032 120.7 . . ?
C022 C032 H032 120.7 . . ?
C018 C033 C032 121.89(13) . . ?
C018 C033 Cl01 118.68(12) . . ?
C032 C033 Cl01 119.43(12) . . ?
