# Electronic Supplementary Material (ESI) for ChemComm.
# 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_zzl_200521
_database_code_depnum_ccdc_archive 'CCDC 2007033'
loop_
_audit_author_name
_audit_author_address
'Zhi-Peng Wang'
;CHONGQING UNIVERSITY
China
;
_audit_update_record             
;
2020-06-02 deposited with the CCDC.	2020-10-13 downloaded from the CCDC.
;
_audit_creation_date             2020-05-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H23 Cl2 N O6'
_chemical_formula_sum            'C23 H23 Cl2 N O6'
_chemical_formula_weight         480.32
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H22 Cl2 N O6'
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 0.0000 0.0000 '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'
N N 0.0311 0.0180 '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'

_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      trigonal
_space_group_IT_number           144
_space_group_name_H-M_alt        'P 31'
_space_group_name_Hall           'P 31'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'

_cell_length_a                   12.39590(15)
_cell_length_b                   12.39590(15)
_cell_length_c                   13.34104(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1775.32(5)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    4956
_cell_measurement_temperature    293.07(10)
_cell_measurement_theta_max      71.6830
_cell_measurement_theta_min      4.1090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.798
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             750
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6370
_diffrn_reflns_point_group_measured_fraction_full 0.789
_diffrn_reflns_point_group_measured_fraction_max 0.757
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.759
_diffrn_reflns_theta_min         4.118
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.07(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -106.00  -7.00   1.00    1.00    --  -35.97 -19.00 -60.00   99
  2  ω     24.00  90.00   1.00    1.00    --   35.97-126.00  90.00   66
  3  ω    -31.00  53.00   1.00    1.00    --   35.97 -57.00-120.00   84
  4  ω     91.00 176.00   1.00    3.00    --  107.97  45.00  90.00   85
  5  ω     38.00 112.00   1.00    3.00    --  107.97-112.00-180.00   74
  6  ω     41.00 126.00   1.00    3.00    --  107.97 -61.00-120.00   85
  7  ω     38.00 129.00   1.00    3.00    --  107.97 -30.00 -60.00   91
  8  ω   -105.00 -17.00   1.00    1.00    --  -35.97 -38.00-180.00   88
  9  ω   -103.00 -19.00   1.00    1.00    --  -35.97 -57.00 -90.00   84
 10  ω   -103.00 -19.00   1.00    1.00    --  -35.97 -57.00  90.00   84
 11  ω     87.00 112.00   1.00    3.00    --  107.97  30.00   0.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1239942000
_diffrn_orient_matrix_UB_12      0.0362170000
_diffrn_orient_matrix_UB_13      -0.0529742000
_diffrn_orient_matrix_UB_21      0.0490297000
_diffrn_orient_matrix_UB_22      -0.0286446000
_diffrn_orient_matrix_UB_23      0.0966268000
_diffrn_orient_matrix_UB_31      -0.0530948000
_diffrn_orient_matrix_UB_32      -0.1358749000
_diffrn_orient_matrix_UB_33      -0.0345169000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.555
_reflns_Friedel_fraction_full    0.578
_reflns_Friedel_fraction_max     0.541
_reflns_number_gt                3413
_reflns_number_total             3530
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3530
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      1.038
_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)+(0.1089P)²+0.0371P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1472
_refine_ls_wR_factor_ref         0.1506
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C16(H16), C20(H20), C19(H19), C13(H13), C23(H23), C15(H15), C22(H22),
 C12(H12)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 -0.18988(17) -0.68150(16) -0.43081(14) 0.0958(5) Uani 1 1 d . . . . .
Cl2 Cl 0.28172(17) 0.0492(2) -1.00654(13) 0.1100(7) Uani 1 1 d . . . . .
O6 O -0.4967(2) -0.2236(3) -0.93982(17) 0.0490(6) Uani 1 1 d . . . . .
O5 O -0.2848(3) -0.1077(3) -0.9409(2) 0.0528(6) Uani 1 1 d . . . . .
C4 C -0.3829(3) -0.1717(3) -0.8990(2) 0.0390(7) Uani 1 1 d . . . . .
O1 O -0.2759(3) -0.3792(3) -0.8363(3) 0.0663(8) Uani 1 1 d . . . . .
O4 O -0.4018(4) -0.0652(4) -0.6511(3) 0.0704(10) Uani 1 1 d . . . . .
N1 N -0.3947(3) -0.2031(3) -0.8009(2) 0.0461(7) Uani 1 1 d . . . . .
H1 H -0.466806 -0.257003 -0.778335 0.055 Uiso 1 1 calc R . . . .
O2 O -0.4455(3) -0.3755(4) -0.6440(3) 0.0695(10) Uani 1 1 d . . . . .
O3 O -0.2672(4) -0.0917(4) -0.5597(2) 0.0784(12) Uani 1 1 d . . . . .
C18 C -0.0802(4) -0.1948(3) -0.8470(2) 0.0407(7) Uani 1 1 d . . . . .
C17 C -0.2035(4) -0.2789(4) -0.7993(3) 0.0440(7) Uani 1 1 d . . . . .
C14 C -0.2332(5) -0.5870(4) -0.4962(4) 0.0598(10) Uani 1 1 d . . . . .
C2 C -0.3186(4) -0.1004(4) -0.6374(3) 0.0480(8) Uani 1 1 d . . . . .
C3 C -0.2898(4) -0.1489(3) -0.7327(2) 0.0428(7) Uani 1 1 d . . . . .
H3 H -0.221661 -0.077141 -0.766848 0.051 Uiso 1 1 calc R . . . .
C9 C -0.2412(3) -0.2375(3) -0.7044(2) 0.0416(7) Uani 1 1 d . . . . .
H9 H -0.167451 -0.192260 -0.661726 0.050 Uiso 1 1 calc R . . . .
C10 C -0.3382(3) -0.3524(4) -0.6475(3) 0.0464(8) Uani 1 1 d . . . . .
C11 C -0.2981(3) -0.4336(4) -0.5977(3) 0.0449(8) Uani 1 1 d . . . . .
C16 C -0.1738(4) -0.3956(4) -0.5794(4) 0.0590(10) Uani 1 1 d . . . . .
H16 H -0.111873 -0.317929 -0.601503 0.071 Uiso 1 1 calc R . . . .
C20 C 0.1209(5) -0.0082(5) -0.8529(4) 0.0620(11) Uani 1 1 d . . . . .
H20 H 0.180280 0.066627 -0.824328 0.074 Uiso 1 1 calc R . . . .
C19 C 0.0094(4) -0.0834(4) -0.8048(3) 0.0495(8) Uani 1 1 d . . . . .
H19 H -0.006077 -0.058853 -0.743120 0.059 Uiso 1 1 calc R . . . .
C5 C -0.5159(4) -0.2194(4) -1.0487(3) 0.0519(9) Uani 1 1 d . . . . .
C13 C -0.3570(5) -0.6285(5) -0.5141(5) 0.0705(13) Uani 1 1 d . . . . .
H13 H -0.418043 -0.707112 -0.492801 0.085 Uiso 1 1 calc R . . . .
C23 C -0.0545(4) -0.2314(5) -0.9387(3) 0.0559(10) Uani 1 1 d . . . . .
H23 H -0.113264 -0.306490 -0.967360 0.067 Uiso 1 1 calc R . . . .
C15 C -0.1415(5) -0.4728(5) -0.5284(5) 0.0697(13) Uani 1 1 d . . . . .
H15 H -0.058261 -0.447162 -0.516125 0.084 Uiso 1 1 calc R . . . .
C22 C 0.0567(5) -0.1580(5) -0.9873(3) 0.0645(12) Uani 1 1 d . . . . .
H22 H 0.073562 -0.182984 -1.048139 0.077 Uiso 1 1 calc R . . . .
C21 C 0.1429(4) -0.0461(5) -0.9440(3) 0.0613(11) Uani 1 1 d . . . . .
C12 C -0.3890(4) -0.5509(4) -0.5645(4) 0.0616(11) Uani 1 1 d . . . . .
H12 H -0.472550 -0.577487 -0.576419 0.074 Uiso 1 1 calc R . . . .
C7 C -0.4540(6) -0.0888(6) -1.0874(4) 0.0840(18) Uani 1 1 d . . . . .
H7A H -0.473070 -0.038770 -1.044068 0.126 Uiso 1 1 calc GR . . . .
H7B H -0.483725 -0.088485 -1.153765 0.126 Uiso 1 1 calc GR . . . .
H7C H -0.365494 -0.055395 -1.089173 0.126 Uiso 1 1 calc GR . . . .
C6 C -0.6570(5) -0.2808(6) -1.0558(4) 0.0710(13) Uani 1 1 d . . . . .
H6A H -0.694760 -0.358825 -1.020667 0.107 Uiso 1 1 calc GR . . . .
H6B H -0.681671 -0.295087 -1.124941 0.107 Uiso 1 1 calc GR . . . .
H6C H -0.683422 -0.227218 -1.026320 0.107 Uiso 1 1 calc GR . . . .
C8 C -0.4681(6) -0.2971(6) -1.0998(4) 0.0778(16) Uani 1 1 d . . . . .
H8A H -0.383295 -0.267336 -1.080234 0.117 Uiso 1 1 calc GR . . . .
H8B H -0.472277 -0.290187 -1.171213 0.117 Uiso 1 1 calc GR . . . .
H8C H -0.518525 -0.382686 -1.080284 0.117 Uiso 1 1 calc GR . . . .
C1 C -0.4290(8) -0.0110(8) -0.5642(6) 0.096(2) Uani 1 1 d . . . . .
H1A H -0.493711 0.006898 -0.581036 0.144 Uiso 1 1 calc GR . . . .
H1B H -0.355296 0.064565 -0.545150 0.144 Uiso 1 1 calc GR . . . .
H1C H -0.455877 -0.068977 -0.509456 0.144 Uiso 1 1 calc GR . . . .


_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 C14 1.746(5) . ?
Cl2 C21 1.738(5) . ?
O6 C4 1.339(4) . ?
O6 C5 1.477(4) . ?
O5 C4 1.207(5) . ?
C4 N1 1.351(4) . ?
O1 C17 1.216(5) . ?
O4 C2 1.318(5) . ?
O4 C1 1.461(6) . ?
N1 C3 1.448(5) . ?
O2 C10 1.213(5) . ?
O3 C2 1.193(5) . ?
C18 C17 1.495(5) . ?
C18 C19 1.387(5) . ?
C18 C23 1.396(5) . ?
C17 C9 1.525(5) . ?
C14 C13 1.373(7) . ?
C14 C15 1.368(7) . ?
C2 C3 1.523(5) . ?
C3 C9 1.541(5) . ?
C9 C10 1.529(5) . ?
C10 C11 1.484(5) . ?
C11 C16 1.389(6) . ?
C11 C12 1.393(6) . ?
C16 C15 1.386(7) . ?
C20 C19 1.380(6) . ?
C20 C21 1.378(7) . ?
C5 C7 1.495(7) . ?
C5 C6 1.521(6) . ?
C5 C8 1.521(7) . ?
C13 C12 1.385(7) . ?
C23 C22 1.375(7) . ?
C22 C21 1.384(8) . ?

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
C4 O6 C5 122.2(3) . . ?
O6 C4 N1 108.6(3) . . ?
O5 C4 O6 126.9(3) . . ?
O5 C4 N1 124.5(3) . . ?
C2 O4 C1 116.2(4) . . ?
C4 N1 C3 122.1(3) . . ?
C19 C18 C17 123.5(3) . . ?
C19 C18 C23 118.7(4) . . ?
C23 C18 C17 117.8(4) . . ?
O1 C17 C18 121.0(3) . . ?
O1 C17 C9 119.2(4) . . ?
C18 C17 C9 119.8(3) . . ?
C13 C14 Cl1 119.8(4) . . ?
C15 C14 Cl1 118.4(4) . . ?
C15 C14 C13 121.8(4) . . ?
O4 C2 C3 113.1(3) . . ?
O3 C2 O4 124.1(4) . . ?
O3 C2 C3 122.7(4) . . ?
N1 C3 C2 112.0(3) . . ?
N1 C3 C9 113.8(3) . . ?
C2 C3 C9 109.2(3) . . ?
C17 C9 C3 109.3(3) . . ?
C17 C9 C10 109.2(3) . . ?
C10 C9 C3 112.3(3) . . ?
O2 C10 C9 119.8(4) . . ?
O2 C10 C11 121.5(4) . . ?
C11 C10 C9 118.7(3) . . ?
C16 C11 C10 122.7(3) . . ?
C16 C11 C12 118.7(4) . . ?
C12 C11 C10 118.6(4) . . ?
C15 C16 C11 120.4(4) . . ?
C21 C20 C19 118.8(4) . . ?
C20 C19 C18 121.1(4) . . ?
O6 C5 C7 111.9(4) . . ?
O6 C5 C6 102.1(3) . . ?
O6 C5 C8 107.4(4) . . ?
C7 C5 C6 111.1(5) . . ?
C7 C5 C8 112.3(5) . . ?
C8 C5 C6 111.7(4) . . ?
C14 C13 C12 118.6(4) . . ?
C22 C23 C18 120.9(4) . . ?
C14 C15 C16 119.4(5) . . ?
C23 C22 C21 118.9(4) . . ?
C20 C21 Cl2 119.3(4) . . ?
C20 C21 C22 121.6(4) . . ?
C22 C21 Cl2 119.1(4) . . ?
C13 C12 C11 121.1(4) . . ?

_shelx_SHELXL_version_number     2017/1

_olex2_date_sample_data_collection 2020-05-21
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.460
_oxdiff_exptl_absorpt_empirical_full_min 0.657
