# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_20180525WLY_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc200tzv
_database_code_depnum_ccdc_archive 'CCDC 1847847'
_audit_update_record             
;
2018-06-07 deposited with the CCDC.
2019-02-12 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 H23 Cl3 N4 O4'
_chemical_formula_weight         501.78

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                   7.3086(4)
_cell_length_b                   11.3812(8)
_cell_length_c                   14.9481(9)
_cell_angle_alpha                68.663(2)
_cell_angle_beta                 88.391(2)
_cell_angle_gamma                88.415(2)
_cell_volume                     1157.51(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    6269
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      27.59

_exptl_crystal_description       block
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.432
_shelx_estimated_absorpt_T_min   0.896
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8141
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.858
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_full        25.010
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             4009
_reflns_number_gt                3565
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0561P)²+1.2625P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4009
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1293
_refine_ls_wR_factor_gt          0.1237
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_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
C1 C 0.9410(3) 0.3263(2) 0.54811(17) 0.0333(5) Uani 1 1 d . . . . .
H1 H 0.976033 0.398831 0.560201 0.040 Uiso 1 1 calc R U . . .
C2 C 0.8941(4) 0.3379(3) 0.45749(18) 0.0407(6) Uani 1 1 d . . . . .
H2 H 0.897182 0.418109 0.407038 0.049 Uiso 1 1 calc R U . . .
C3 C 0.8413(3) 0.2315(3) 0.43850(18) 0.0390(6) Uani 1 1 d . . . . .
H3 H 0.807745 0.240378 0.375393 0.047 Uiso 1 1 calc R U . . .
C4 C 0.8381(3) 0.1159(2) 0.51000(18) 0.0348(5) Uani 1 1 d . . . . .
H4 H 0.803092 0.044825 0.495962 0.042 Uiso 1 1 calc R U . . .
C5 C 0.8860(3) 0.0996(2) 0.60516(17) 0.0298(5) Uani 1 1 d . . . . .
C6 C 0.8812(3) -0.0195(2) 0.68096(19) 0.0348(5) Uani 1 1 d . . . . .
H6 H 0.847090 -0.092026 0.668602 0.042 Uiso 1 1 calc R U . . .
C7 C 0.9255(3) -0.0303(2) 0.77146(19) 0.0369(6) Uani 1 1 d . . . . .
H7 H 0.920161 -0.110411 0.821940 0.044 Uiso 1 1 calc R U . . .
C8 C 0.9792(3) 0.0758(2) 0.79174(17) 0.0326(5) Uani 1 1 d . . . . .
H8 H 1.011582 0.066193 0.855152 0.039 Uiso 1 1 calc R U . . .
C9 C 0.9846(3) 0.1921(2) 0.71999(16) 0.0275(5) Uani 1 1 d . . . . .
C10 C 0.9382(3) 0.2079(2) 0.62404(16) 0.0264(5) Uani 1 1 d . . . . .
C11 C 1.0749(3) 0.2954(2) 0.82552(16) 0.0315(5) Uani 1 1 d . . . . .
H11A H 1.196864 0.255661 0.844784 0.038 Uiso 1 1 calc R U . . .
H11B H 0.982218 0.244866 0.872241 0.038 Uiso 1 1 calc R U . . .
C12 C 1.0717(3) 0.4288(2) 0.82345(17) 0.0328(5) Uani 1 1 d . . . . .
H12A H 1.122996 0.431390 0.883289 0.039 Uiso 1 1 calc R U . . .
H12B H 1.145718 0.483449 0.768250 0.039 Uiso 1 1 calc R U . . .
C13 C 0.8599(3) 0.6005(2) 0.79988(16) 0.0317(5) Uani 1 1 d . . . . .
H13A H 0.935454 0.653121 0.744552 0.038 Uiso 1 1 calc R U . . .
H13B H 0.895028 0.617086 0.857596 0.038 Uiso 1 1 calc R U . . .
C14 C 0.6591(3) 0.6305(2) 0.78033(15) 0.0296(5) Uani 1 1 d . . . . .
H14A H 0.586025 0.581991 0.838163 0.036 Uiso 1 1 calc R U . . .
H14B H 0.635653 0.721364 0.766762 0.036 Uiso 1 1 calc R U . . .
C15 C 0.6144(3) 0.6827(2) 0.60993(15) 0.0240(4) Uani 1 1 d . . . . .
C16 C 0.5611(3) 0.69955(19) 0.44391(14) 0.0204(4) Uani 1 1 d . . . . .
C17 C 0.5682(3) 0.89927(19) 0.31816(14) 0.0219(4) Uani 1 1 d . . . . .
C18 C 0.5217(3) 0.8433(2) 0.25691(15) 0.0245(4) Uani 1 1 d . . . . .
H18 H 0.502460 0.892895 0.191222 0.029 Uiso 1 1 calc R U . . .
C19 C 0.5010(3) 0.7087(2) 0.29060(14) 0.0233(4) Uani 1 1 d . . . . .
C20 C 0.5998(3) 1.0366(2) 0.29357(16) 0.0291(5) Uani 1 1 d . . . . .
H20A H 0.570348 1.082788 0.226077 0.044 Uiso 1 1 calc R U . . .
H20B H 0.728446 1.049356 0.303863 0.044 Uiso 1 1 calc R U . . .
H20C H 0.521356 1.067935 0.334633 0.044 Uiso 1 1 calc R U . . .
C21 C 0.3732(4) 0.7398(3) 1.01679(18) 0.0437(6) Uani 1 1 d . . . . .
H21 H 0.359808 0.690204 1.087164 0.052 Uiso 1 1 calc R U . . .
Cl1 Cl 0.30564(14) 0.89724(8) 0.99372(6) 0.0683(3) Uani 1 1 d . . . . .
Cl2 Cl 0.23565(14) 0.67452(10) 0.95332(6) 0.0767(3) Uani 1 1 d . . . . .
Cl3 Cl 0.60341(12) 0.73625(14) 0.98144(7) 0.0953(4) Uani 1 1 d . . . . .
N1 N 0.6013(3) 0.59975(17) 0.69929(13) 0.0287(4) Uani 1 1 d . . . . .
H1A H 0.556739 0.524777 0.709629 0.034 Uiso 1 1 calc R U . . .
N2 N 0.5766(2) 0.63201(16) 0.54021(12) 0.0236(4) Uani 1 1 d . . . . .
H2A H 0.561456 0.549978 0.559859 0.028 Uiso 1 1 calc R U . . .
N3 N 0.5908(2) 0.82457(16) 0.41272(12) 0.0228(4) Uani 1 1 d . . . . .
H3A H 0.625124 0.858680 0.453625 0.027 Uiso 1 1 calc R U . . .
N4 N 0.5188(2) 0.63895(16) 0.38748(12) 0.0222(4) Uani 1 1 d . . . . .
O1 O 1.0350(2) 0.30105(15) 0.73116(11) 0.0319(4) Uani 1 1 d . . . . .
O2 O 0.8864(2) 0.47089(15) 0.81473(12) 0.0323(4) Uani 1 1 d . . . . .
O3 O 0.6537(2) 0.79467(14) 0.58884(11) 0.0293(4) Uani 1 1 d . . . . .
O4 O 0.4694(2) 0.65344(15) 0.23425(11) 0.0322(4) Uani 1 1 d . . . . .


_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
C1 C2 1.365(4) . ?
C1 C10 1.411(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.406(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.360(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.419(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.417(4) . ?
C5 C10 1.424(3) . ?
C6 C7 1.361(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.415(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.368(3) . ?
C8 H8 0.9500 . ?
C9 O1 1.372(3) . ?
C9 C10 1.428(3) . ?
C11 O1 1.426(3) . ?
C11 C12 1.506(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O2 1.418(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O2 1.418(3) . ?
C13 C14 1.510(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N1 1.454(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O3 1.237(3) . ?
C15 N1 1.328(3) . ?
C15 N2 1.399(3) . ?
C16 N4 1.316(3) . ?
C16 N3 1.348(3) . ?
C16 N2 1.369(3) . ?
C17 C18 1.346(3) . ?
C17 N3 1.371(3) . ?
C17 C20 1.493(3) . ?
C18 C19 1.439(3) . ?
C18 H18 0.9500 . ?
C19 O4 1.250(3) . ?
C19 N4 1.383(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 Cl2 1.752(3) . ?
C21 Cl3 1.753(3) . ?
C21 Cl1 1.756(3) . ?
C21 H21 1.0000 . ?
N1 H1A 0.8800 . ?
N2 H2A 0.8800 . ?
N3 H3A 0.8800 . ?

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
C2 C1 C10 120.8(2) . . ?
C2 C1 H1 119.6 . . ?
C10 C1 H1 119.6 . . ?
C1 C2 C3 120.3(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 121.2(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 122.2(2) . . ?
C6 C5 C10 119.7(2) . . ?
C4 C5 C10 118.2(2) . . ?
C7 C6 C5 120.1(2) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 121.2(2) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 120.0(2) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 O1 125.0(2) . . ?
C8 C9 C10 120.7(2) . . ?
O1 C9 C10 114.2(2) . . ?
C1 C10 C5 119.2(2) . . ?
C1 C10 C9 122.5(2) . . ?
C5 C10 C9 118.3(2) . . ?
O1 C11 C12 107.43(18) . . ?
O1 C11 H11A 110.2 . . ?
C12 C11 H11A 110.2 . . ?
O1 C11 H11B 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
O2 C12 C11 107.13(18) . . ?
O2 C12 H12A 110.3 . . ?
C11 C12 H12A 110.3 . . ?
O2 C12 H12B 110.3 . . ?
C11 C12 H12B 110.3 . . ?
H12A C12 H12B 108.5 . . ?
O2 C13 C14 106.77(18) . . ?
O2 C13 H13A 110.4 . . ?
C14 C13 H13A 110.4 . . ?
O2 C13 H13B 110.4 . . ?
C14 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
N1 C14 C13 111.51(18) . . ?
N1 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
N1 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
O3 C15 N1 124.18(19) . . ?
O3 C15 N2 122.25(19) . . ?
N1 C15 N2 113.56(18) . . ?
N4 C16 N3 123.99(18) . . ?
N4 C16 N2 118.33(18) . . ?
N3 C16 N2 117.68(17) . . ?
C18 C17 N3 117.97(19) . . ?
C18 C17 C20 126.45(19) . . ?
N3 C17 C20 115.58(18) . . ?
C17 C18 C19 120.24(19) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
O4 C19 N4 119.39(19) . . ?
O4 C19 C18 121.55(19) . . ?
N4 C19 C18 119.05(18) . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Cl2 C21 Cl3 110.31(15) . . ?
Cl2 C21 Cl1 109.95(15) . . ?
Cl3 C21 Cl1 108.67(17) . . ?
Cl2 C21 H21 109.3 . . ?
Cl3 C21 H21 109.3 . . ?
Cl1 C21 H21 109.3 . . ?
C15 N1 C14 121.27(19) . . ?
C15 N1 H1A 119.4 . . ?
C14 N1 H1A 119.4 . . ?
C16 N2 C15 125.39(18) . . ?
C16 N2 H2A 117.3 . . ?
C15 N2 H2A 117.3 . . ?
C16 N3 C17 120.90(17) . . ?
C16 N3 H3A 119.5 . . ?
C17 N3 H3A 119.5 . . ?
C16 N4 C19 117.68(18) . . ?
C9 O1 C11 118.10(18) . . ?
C12 O2 C13 114.73(18) . . ?

_refine_diff_density_max         0.710
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.055



