# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_exp_7324
_database_code_depnum_ccdc_archive 'CCDC 1948643'
loop_
_audit_author_name
_audit_author_address
cc
;quanzhou nnormal university
China
;
_audit_update_record             
;
2019-10-09 deposited with the CCDC.	2019-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H29 Cl N2 O6'
_chemical_formula_weight         440.91

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   10.3139(9)
_cell_length_b                   11.3380(10)
_cell_length_c                   12.3840(10)
_cell_angle_alpha                63.811(8)
_cell_angle_beta                 72.144(8)
_cell_angle_gamma                69.542(8)
_cell_volume                     1197.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1819
_cell_measurement_theta_min      3.6050
_cell_measurement_theta_max      21.8970

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.196
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_T_min  0.76036
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8370
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.331
_diffrn_reflns_theta_max         25.017
_diffrn_reflns_theta_full        25.017
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4219
_reflns_number_gt                2561
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0527P)²+0.1809P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.078(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4219
_refine_ls_number_parameters     321
_refine_ls_number_restraints     948
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.005
_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
Cl1 Cl 0.39895(11) -0.15433(8) 0.21601(9) 0.1057(4) Uani 1 1 d . U . . .
N1 N 0.2911(2) 0.4944(2) 0.14344(17) 0.0474(5) Uani 1 1 d . U . . .
N2 N 0.2916(2) 0.5968(2) 0.02898(18) 0.0527(6) Uani 1 1 d . U . . .
H2A H 0.333040 0.578840 -0.035730 0.063 Uiso 1 1 calc R U . . .
O1 O -0.1614(2) 0.2670(2) 0.43106(19) 0.0916(7) Uani 1 1 d . U . . .
O2 O -0.0869(2) 0.4166(2) 0.44941(18) 0.0787(6) Uani 1 1 d . U . . .
O3 O 0.37520(17) 0.37255(18) 0.31404(15) 0.0575(5) Uani 1 1 d . U . . .
O4 O 0.50100(17) 0.50851(18) 0.15460(16) 0.0589(5) Uani 1 1 d . U . . .
O5 O 0.2481(2) 0.80763(19) -0.0979(2) 0.0860(7) Uani 1 1 d . U . . .
O6 O 0.1565(2) 0.7600(2) 0.1046(2) 0.0892(7) Uani 1 1 d . U . . .
C1 C 0.3372(3) 0.0112(3) 0.2114(3) 0.0670(8) Uani 1 1 d . U . . .
C2 C 0.3786(3) 0.1145(3) 0.1078(3) 0.0784(9) Uani 1 1 d . U . . .
H2 H 0.438866 0.095742 0.040914 0.094 Uiso 1 1 calc R U . . .
C3 C 0.3306(3) 0.2456(3) 0.1033(3) 0.0640(8) Uani 1 1 d . U . . .
H3 H 0.360047 0.314964 0.033411 0.077 Uiso 1 1 calc R U . . .
C4 C 0.2393(2) 0.2762(3) 0.2008(2) 0.0486(6) Uani 1 1 d . U . . .
C5 C 0.2012(3) 0.1695(3) 0.3047(2) 0.0577(7) Uani 1 1 d . U . . .
H5 H 0.141667 0.187279 0.372245 0.069 Uiso 1 1 calc R U . . .
C6 C 0.2496(3) 0.0372(3) 0.3102(3) 0.0628(8) Uani 1 1 d . U . . .
H6 H 0.222618 -0.033217 0.380464 0.075 Uiso 1 1 calc R U . . .
C7 C 0.1845(3) 0.4188(2) 0.1915(2) 0.0456(6) Uani 1 1 d . U . . .
C8 C 0.0525(3) 0.4864(3) 0.2154(2) 0.0486(6) Uani 1 1 d . U . . .
H8 H 0.041690 0.573365 0.210720 0.058 Uiso 1 1 calc R U . . .
C9 C -0.0844(2) 0.4453(3) 0.2493(2) 0.0532(7) Uani 1 1 d . U . . .
C10 C -0.1149(3) 0.3639(3) 0.3856(3) 0.0573(7) Uani 1 1 d . U . . .
C11 C -0.0873(3) 0.3674(3) 0.1766(3) 0.0762(9) Uani 1 1 d . U . . .
H11A H -0.065735 0.419245 0.090696 0.114 Uiso 1 1 calc R U . . .
H11B H -0.179192 0.352454 0.196147 0.114 Uiso 1 1 calc R U . . .
H11C H -0.018793 0.281659 0.197331 0.114 Uiso 1 1 calc R U . . .
C12 C -0.2038(3) 0.5769(3) 0.2223(3) 0.0794(9) Uani 1 1 d . U . . .
H12A H -0.207622 0.624552 0.271329 0.119 Uiso 1 1 calc R U . . .
H12B H -0.291898 0.554570 0.241569 0.119 Uiso 1 1 calc R U . . .
H12C H -0.186075 0.633445 0.137265 0.119 Uiso 1 1 calc R U . . .
C13 C -0.1112(4) 0.3503(4) 0.5811(3) 0.1062(12) Uani 1 1 d . U . . .
H13A H -0.209609 0.354479 0.611140 0.159 Uiso 1 1 calc R U . . .
H13B H -0.081721 0.395384 0.615885 0.159 Uiso 1 1 calc R U . . .
H13C H -0.058363 0.257156 0.603802 0.159 Uiso 1 1 calc R U . . .
C14 C 0.3993(3) 0.4616(2) 0.2009(2) 0.0463(6) Uani 1 1 d . U . . .
C15 C 0.4874(3) 0.3142(3) 0.3853(3) 0.0690(8) Uani 1 1 d . U . . .
H15 H 0.579332 0.306566 0.331198 0.083 Uiso 0.621(7) 1 d R U P A 1
H15A H 0.550485 0.373715 0.357033 0.083 Uiso 0.379(7) 1 d R U P A 2
C16 C 0.4718(6) 0.4052(7) 0.4465(6) 0.093(2) Uani 0.621(7) 1 d . U P A 1
H16A H 0.480422 0.492938 0.386064 0.139 Uiso 0.621(7) 1 calc R U P A 1
H16B H 0.543851 0.368199 0.494959 0.139 Uiso 0.621(7) 1 calc R U P A 1
H16C H 0.381042 0.413789 0.498386 0.139 Uiso 0.621(7) 1 calc R U P A 1
C17 C 0.4699(10) 0.1765(8) 0.4696(8) 0.132(4) Uani 0.621(7) 1 d . U P A 1
H17A H 0.381575 0.184051 0.524935 0.199 Uiso 0.621(7) 1 calc R U P A 1
H17B H 0.545220 0.129523 0.515369 0.199 Uiso 0.621(7) 1 calc R U P A 1
H17C H 0.471791 0.126798 0.423124 0.199 Uiso 0.621(7) 1 calc R U P A 1
C16' C 0.4108(14) 0.2922(17) 0.5208(10) 0.136(5) Uani 0.379(7) 1 d . U P A 2
H16D H 0.365097 0.378719 0.528094 0.204 Uiso 0.379(7) 1 calc R U P A 2
H16E H 0.478516 0.242022 0.574186 0.204 Uiso 0.379(7) 1 calc R U P A 2
H16F H 0.342012 0.242376 0.543092 0.204 Uiso 0.379(7) 1 calc R U P A 2
C17' C 0.5679(13) 0.1806(12) 0.3744(13) 0.111(4) Uani 0.379(7) 1 d . U P A 2
H17D H 0.503392 0.128926 0.389195 0.167 Uiso 0.379(7) 1 calc R U P A 2
H17E H 0.629190 0.131408 0.433357 0.167 Uiso 0.379(7) 1 calc R U P A 2
H17F H 0.622811 0.195580 0.293500 0.167 Uiso 0.379(7) 1 calc R U P A 2
C18 C 0.2256(3) 0.7263(3) 0.0205(3) 0.0627(8) Uani 1 1 d . U . . .
C19 C 0.1655(5) 0.9480(3) -0.1268(4) 0.1157(14) Uani 1 1 d . U . . .
H19 H 0.072242 0.954546 -0.074507 0.139 Uiso 0.625(9) 1 d R U P B 1
H19A H 0.137392 0.968408 -0.052566 0.139 Uiso 0.375(9) 1 d R U P B 2
C20 C 0.1552(14) 0.9941(8) -0.2686(11) 0.190(5) Uani 0.625(9) 1 d . U P B 1
H20A H 0.109239 1.089001 -0.300279 0.285 Uiso 0.625(9) 1 calc R U P B 1
H20B H 0.102046 0.942575 -0.273584 0.285 Uiso 0.625(9) 1 calc R U P B 1
H20C H 0.248105 0.977916 -0.315688 0.285 Uiso 0.625(9) 1 calc R U P B 1
C21 C 0.2376(10) 1.0270(8) -0.1142(12) 0.147(4) Uani 0.625(9) 1 d . U P B 1
H21A H 0.235038 1.002804 -0.028978 0.220 Uiso 0.625(9) 1 calc R U P B 1
H21B H 0.192519 1.121705 -0.149816 0.220 Uiso 0.625(9) 1 calc R U P B 1
H21C H 0.333614 1.009749 -0.155255 0.220 Uiso 0.625(9) 1 calc R U P B 1
C20' C 0.0439(14) 0.9649(11) -0.1655(14) 0.112(4) Uani 0.375(9) 1 d . U P B 2
H20D H 0.069038 0.929607 -0.228779 0.169 Uiso 0.375(9) 1 calc R U P B 2
H20E H -0.002573 1.059775 -0.196674 0.169 Uiso 0.375(9) 1 calc R U P B 2
H20F H -0.018210 0.917081 -0.097619 0.169 Uiso 0.375(9) 1 calc R U P B 2
C21' C 0.256(2) 1.0382(15) -0.216(2) 0.187(8) Uani 0.375(9) 1 d . U P B 2
H21D H 0.285641 1.021486 -0.290989 0.281 Uiso 0.375(9) 1 calc R U P B 2
H21E H 0.337041 1.020573 -0.183833 0.281 Uiso 0.375(9) 1 calc R U P B 2
H21F H 0.204103 1.131127 -0.232899 0.281 Uiso 0.375(9) 1 calc R U P B 2


_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 C1 1.739(3) . ?
N1 C14 1.361(3) . ?
N1 N2 1.380(3) . ?
N1 C7 1.451(3) . ?
N2 C18 1.356(3) . ?
O1 C10 1.188(3) . ?
O2 C10 1.319(3) . ?
O2 C13 1.444(3) . ?
O3 C14 1.326(3) . ?
O3 C15 1.460(3) . ?
O4 C14 1.210(3) . ?
O5 C18 1.342(3) . ?
O5 C19 1.457(4) . ?
O6 C18 1.202(3) . ?
C1 C6 1.362(4) . ?
C1 C2 1.374(4) . ?
C2 C3 1.374(4) . ?
C3 C4 1.382(3) . ?
C4 C5 1.387(3) . ?
C4 C7 1.477(3) . ?
C5 C6 1.383(4) . ?
C7 C8 1.324(3) . ?
C8 C9 1.520(3) . ?
C9 C10 1.517(4) . ?
C9 C11 1.525(4) . ?
C9 C12 1.544(4) . ?
C15 C16 1.471(6) . ?
C15 C17 1.484(7) . ?
C15 C17' 1.496(11) . ?
C15 C16' 1.567(12) . ?
C19 C20' 1.399(11) . ?
C19 C21 1.429(9) . ?
C19 C21' 1.476(15) . ?
C19 C20 1.622(12) . ?

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
C14 N1 N2 117.57(18) . . ?
C14 N1 C7 123.08(19) . . ?
N2 N1 C7 119.07(19) . . ?
C18 N2 N1 118.7(2) . . ?
C10 O2 C13 117.9(2) . . ?
C14 O3 C15 117.53(19) . . ?
C18 O5 C19 115.2(3) . . ?
C6 C1 C2 120.7(3) . . ?
C6 C1 Cl1 119.9(2) . . ?
C2 C1 Cl1 119.3(2) . . ?
C1 C2 C3 119.8(3) . . ?
C2 C3 C4 121.2(3) . . ?
C3 C4 C5 117.6(2) . . ?
C3 C4 C7 120.0(2) . . ?
C5 C4 C7 122.3(2) . . ?
C6 C5 C4 121.5(3) . . ?
C1 C6 C5 119.1(3) . . ?
C8 C7 N1 116.9(2) . . ?
C8 C7 C4 128.7(2) . . ?
N1 C7 C4 114.3(2) . . ?
C7 C8 C9 130.6(2) . . ?
C10 C9 C8 110.3(2) . . ?
C10 C9 C11 110.5(2) . . ?
C8 C9 C11 113.5(2) . . ?
C10 C9 C12 106.8(2) . . ?
C8 C9 C12 107.3(2) . . ?
C11 C9 C12 108.2(2) . . ?
O1 C10 O2 123.4(3) . . ?
O1 C10 C9 125.2(3) . . ?
O2 C10 C9 111.4(2) . . ?
O4 C14 O3 125.8(2) . . ?
O4 C14 N1 124.4(2) . . ?
O3 C14 N1 109.86(19) . . ?
O3 C15 C16 107.9(3) . . ?
O3 C15 C17 105.1(3) . . ?
C16 C15 C17 114.6(5) . . ?
O3 C15 C17' 107.7(5) . . ?
O3 C15 C16' 105.4(5) . . ?
C17' C15 C16' 110.1(8) . . ?
O6 C18 O5 126.8(3) . . ?
O6 C18 N2 125.3(3) . . ?
O5 C18 N2 107.8(3) . . ?
C20' C19 O5 109.7(5) . . ?
C21 C19 O5 110.5(5) . . ?
C20' C19 C21' 114.2(11) . . ?
O5 C19 C21' 108.7(8) . . ?
C21 C19 C20 111.4(6) . . ?
O5 C19 C20 102.0(5) . . ?

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.035

