# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_a_a
_database_code_depnum_ccdc_archive 'CCDC 1476215'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 Cl N2 O3'
_chemical_formula_weight         372.84

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'

_symmetry_cell_setting           Monoclinic'
_symmetry_space_group_name_H-M   P2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.114(4)
_cell_length_b                   8.760(3)
_cell_length_c                   11.937(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.233(6)
_cell_angle_gamma                90.00
_cell_volume                     943.1(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1333
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      23.71

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9481
_exptl_absorpt_correction_T_max  0.9607
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX2 CCD area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5089
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0710
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         24.68
_reflns_number_total             3191
_reflns_number_gt                2186
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Altomare,1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL(Sheldrick, 2008)'
_computing_publication_material  'WINGX (Farrugia,1999)'


_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 > 2sigma(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)+(0.0379P)²+0.0476P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.58(10)
_refine_ls_number_reflns         3191
_refine_ls_number_parameters     235
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.025
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.12858(14) 0.50672(14) 0.05826(10) 0.0756(4) Uani 1 1 d U . .
O1 O 0.1859(3) 0.8174(3) 0.5509(2) 0.0564(8) Uani 1 1 d U . .
N1 N 0.2267(3) 0.9201(3) 0.2209(2) 0.0401(8) Uani 1 1 d U . .
N2 N 0.2708(3) 0.9667(3) 0.4181(2) 0.0407(8) Uani 1 1 d U . .
C5 C 0.1420(4) 0.7952(4) 0.2452(3) 0.0357(8) Uani 1 1 d U . .
O3 O 0.6718(4) 1.1146(5) 0.0513(3) 0.0879(11) Uani 1 1 d U . .
C7 C 0.1930(4) 0.8421(4) 0.4506(3) 0.0404(9) Uani 1 1 d U . .
C8 C 0.2847(4) 0.9981(5) 0.3072(3) 0.0377(8) Uani 1 1 d U . .
C3 C -0.0273(4) 0.5989(4) 0.1734(3) 0.0478(10) Uani 1 1 d U . .
C9 C 0.3678(4) 1.1476(4) 0.3028(3) 0.0403(9) Uani 1 1 d U . .
C6 C 0.1236(4) 0.7539(4) 0.3557(3) 0.0383(9) Uani 1 1 d U . .
C2 C -0.0468(5) 0.5558(4) 0.2818(3) 0.0564(12) Uani 1 1 d U . .
H2 H -0.1106 0.4763 0.2933 0.068 Uiso 1 1 calc R . .
C4 C 0.0664(4) 0.7144(4) 0.1530(3) 0.0456(10) Uani 1 1 d U . .
H4 H 0.0797 0.7390 0.0794 0.055 Uiso 1 1 calc R . .
C15 C 0.4736(4) 1.1573(4) 0.2136(3) 0.0397(9) Uani 1 1 d U . .
H15 H 0.4205 1.1203 0.1415 0.048 Uiso 1 1 calc R . .
O2 O 0.6020(5) 0.8458(4) 0.3448(3) 0.1079(14) Uani 1 1 d U . .
C1 C 0.0297(5) 0.6326(4) 0.3717(3) 0.0499(10) Uani 1 1 d U . .
H1 H 0.0187 0.6032 0.4449 0.060 Uiso 1 1 calc R . .
C17 C 0.5935(5) 0.8971(5) 0.2510(4) 0.0581(12) Uani 1 1 d U . .
C19 C 0.7198(5) 1.0943(5) 0.1485(4) 0.0513(10) Uani 1 1 d U . .
C16 C 0.6187(4) 1.0693(4) 0.2385(3) 0.0457(10) Uani 1 1 d U . .
H16 H 0.6711 1.1066 0.3107 0.055 Uiso 1 1 calc R . .
C14 C 0.4968(5) 1.3308(4) 0.2030(4) 0.0530(11) Uani 1 1 d U . .
H14A H 0.5787 1.3651 0.2582 0.064 Uiso 1 1 calc R . .
H14B H 0.5180 1.3564 0.1279 0.064 Uiso 1 1 calc R . .
C10 C 0.4397(5) 1.1694(5) 0.4274(3) 0.0570(11) Uani 1 1 d U . .
H10A H 0.5401 1.1296 0.4389 0.068 Uiso 1 1 calc R . .
H10B H 0.4426 1.2767 0.4477 0.068 Uiso 1 1 calc R . .
C11 C 0.3424(5) 1.0810(5) 0.4977(3) 0.0551(11) Uani 1 1 d U . .
H11A H 0.4014 1.0327 0.5621 0.066 Uiso 1 1 calc R . .
H11B H 0.2696 1.1472 0.5245 0.066 Uiso 1 1 calc R . .
C12 C 0.2591(4) 1.2772(4) 0.2642(4) 0.0641(12) Uani 1 1 d U . .
H12A H 0.1850 1.2434 0.2027 0.077 Uiso 1 1 calc R . .
H12B H 0.2094 1.3115 0.3262 0.077 Uiso 1 1 calc R . .
C13 C 0.3528(5) 1.4051(5) 0.2248(4) 0.0714(14) Uani 1 1 d U . .
H13A H 0.3720 1.4832 0.2826 0.086 Uiso 1 1 calc R . .
H13B H 0.3024 1.4516 0.1561 0.086 Uiso 1 1 calc R . .
C18 C 0.5548(6) 0.8018(5) 0.1497(4) 0.0880(16) Uani 1 1 d U . .
H18A H 0.5422 0.6979 0.1721 0.132 Uiso 1 1 calc R . .
H18B H 0.6328 0.8072 0.1037 0.132 Uiso 1 1 calc R . .
H18C H 0.4641 0.8382 0.1072 0.132 Uiso 1 1 calc R . .
C20 C 0.8803(5) 1.0926(7) 0.1888(5) 0.0930(18) Uani 1 1 d U . .
H20A H 0.9336 1.1092 0.1261 0.139 Uiso 1 1 calc R . .
H20B H 0.9077 0.9954 0.2228 0.139 Uiso 1 1 calc R . .
H20C H 0.9041 1.1719 0.2439 0.139 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 C3 1.740(4) . ?
O1 C7 1.228(4) . ?
N1 C8 1.285(4) . ?
N1 C5 1.393(4) . ?
N2 C8 1.376(4) . ?
N2 C7 1.387(5) . ?
N2 C11 1.467(4) . ?
C5 C6 1.401(5) . ?
C5 C4 1.403(5) . ?
O3 C19 1.194(5) . ?
C7 C6 1.440(5) . ?
C8 C9 1.518(5) . ?
C3 C2 1.384(5) . ?
C3 C4 1.368(5) . ?
C9 C15 1.538(5) . ?
C9 C12 1.534(5) . ?
C9 C10 1.548(5) . ?
C6 C1 1.395(5) . ?
C2 C1 1.370(5) . ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?
C15 C16 1.523(5) . ?
C15 C14 1.543(5) . ?
C15 H15 0.9800 . ?
O2 C17 1.199(5) . ?
C1 H1 0.9300 . ?
C17 C18 1.470(6) . ?
C17 C16 1.536(6) . ?
C19 C20 1.472(6) . ?
C19 C16 1.528(5) . ?
C16 H16 0.9800 . ?
C14 C13 1.520(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C10 C11 1.517(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.523(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C8 N1 C5 115.3(3) . . ?
C8 N2 C7 123.2(3) . . ?
C8 N2 C11 113.1(3) . . ?
C7 N2 C11 123.7(3) . . ?
N1 C5 C6 122.9(3) . . ?
N1 C5 C4 117.2(3) . . ?
C6 C5 C4 119.7(3) . . ?
O1 C7 N2 120.7(3) . . ?
O1 C7 C6 126.5(3) . . ?
N2 C7 C6 112.7(3) . . ?
N1 C8 N2 125.6(3) . . ?
N1 C8 C9 125.5(3) . . ?
N2 C8 C9 108.7(3) . . ?
C2 C3 C4 122.3(4) . . ?
C2 C3 Cl1 119.2(3) . . ?
C4 C3 Cl1 118.5(3) . . ?
C8 C9 C15 115.9(3) . . ?
C8 C9 C12 110.2(3) . . ?
C15 C9 C12 101.1(3) . . ?
C8 C9 C10 102.6(3) . . ?
C15 C9 C10 115.9(3) . . ?
C12 C9 C10 111.4(3) . . ?
C1 C6 C5 119.0(3) . . ?
C1 C6 C7 120.6(3) . . ?
C5 C6 C7 120.2(3) . . ?
C3 C2 C1 118.7(4) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C16 C15 C9 116.7(3) . . ?
C16 C15 C14 112.9(3) . . ?
C9 C15 C14 102.6(3) . . ?
C16 C15 H15 108.1 . . ?
C9 C15 H15 108.1 . . ?
C14 C15 H15 108.1 . . ?
C2 C1 C6 121.3(4) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
O2 C17 C18 122.1(5) . . ?
O2 C17 C16 117.9(5) . . ?
C18 C17 C16 119.9(4) . . ?
O3 C19 C20 121.9(4) . . ?
O3 C19 C16 122.0(4) . . ?
C20 C19 C16 116.1(4) . . ?
C15 C16 C19 112.6(3) . . ?
C15 C16 C17 112.2(3) . . ?
C19 C16 C17 108.9(3) . . ?
C15 C16 H16 107.6 . . ?
C19 C16 H16 107.6 . . ?
C17 C16 H16 107.6 . . ?
C13 C14 C15 106.0(3) . . ?
C13 C14 H14A 110.5 . . ?
C15 C14 H14A 110.5 . . ?
C13 C14 H14B 110.5 . . ?
C15 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
C11 C10 C9 105.5(3) . . ?
C11 C10 H10A 110.6 . . ?
C9 C10 H10A 110.6 . . ?
C11 C10 H10B 110.6 . . ?
C9 C10 H10B 110.6 . . ?
H10A C10 H10B 108.8 . . ?
N2 C11 C10 103.4(3) . . ?
N2 C11 H11A 111.1 . . ?
C10 C11 H11A 111.1 . . ?
N2 C11 H11B 111.1 . . ?
C10 C11 H11B 111.1 . . ?
H11A C11 H11B 109.1 . . ?
C13 C12 C9 105.7(3) . . ?
C13 C12 H12A 110.6 . . ?
C9 C12 H12A 110.6 . . ?
C13 C12 H12B 110.6 . . ?
C9 C12 H12B 110.6 . . ?
H12A C12 H12B 108.7 . . ?
C12 C13 C14 105.9(3) . . ?
C12 C13 H13A 110.6 . . ?
C14 C13 H13A 110.6 . . ?
C12 C13 H13B 110.6 . . ?
C14 C13 H13B 110.6 . . ?
H13A C13 H13B 108.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
C8 N1 C5 C6 -1.6(5) . . . . ?
C8 N1 C5 C4 174.7(3) . . . . ?
C8 N2 C7 O1 178.7(3) . . . . ?
C11 N2 C7 O1 -3.3(6) . . . . ?
C8 N2 C7 C6 -2.5(5) . . . . ?
C11 N2 C7 C6 175.4(3) . . . . ?
C5 N1 C8 N2 0.8(5) . . . . ?
C5 N1 C8 C9 -173.3(3) . . . . ?
C7 N2 C8 N1 1.4(6) . . . . ?
C11 N2 C8 N1 -176.7(4) . . . . ?
C7 N2 C8 C9 176.3(3) . . . . ?
C11 N2 C8 C9 -1.8(4) . . . . ?
N1 C8 C9 C15 -40.9(5) . . . . ?
N2 C8 C9 C15 144.2(3) . . . . ?
N1 C8 C9 C12 73.1(4) . . . . ?
N2 C8 C9 C12 -101.8(4) . . . . ?
N1 C8 C9 C10 -168.2(4) . . . . ?
N2 C8 C9 C10 16.8(4) . . . . ?
N1 C5 C6 C1 176.2(3) . . . . ?
C4 C5 C6 C1 -0.1(5) . . . . ?
N1 C5 C6 C7 0.4(5) . . . . ?
C4 C5 C6 C7 -175.9(3) . . . . ?
O1 C7 C6 C1 4.6(6) . . . . ?
N2 C7 C6 C1 -174.1(3) . . . . ?
O1 C7 C6 C5 -179.7(4) . . . . ?
N2 C7 C6 C5 1.7(5) . . . . ?
C4 C3 C2 C1 0.5(6) . . . . ?
Cl1 C3 C2 C1 -177.8(3) . . . . ?
C2 C3 C4 C5 -2.0(6) . . . . ?
Cl1 C3 C4 C5 176.4(3) . . . . ?
N1 C5 C4 C3 -174.8(3) . . . . ?
C6 C5 C4 C3 1.7(5) . . . . ?
C8 C9 C15 C16 -74.4(4) . . . . ?
C12 C9 C15 C16 166.5(3) . . . . ?
C10 C9 C15 C16 46.0(4) . . . . ?
C8 C9 C15 C14 161.6(3) . . . . ?
C12 C9 C15 C14 42.5(4) . . . . ?
C10 C9 C15 C14 -78.0(4) . . . . ?
C3 C2 C1 C6 1.2(6) . . . . ?
C5 C6 C1 C2 -1.4(6) . . . . ?
C7 C6 C1 C2 174.4(4) . . . . ?
C9 C15 C16 C19 -176.4(3) . . . . ?
C14 C15 C16 C19 -57.9(4) . . . . ?
C9 C15 C16 C17 60.4(5) . . . . ?
C14 C15 C16 C17 178.9(4) . . . . ?
O3 C19 C16 C15 -32.9(6) . . . . ?
C20 C19 C16 C15 146.8(4) . . . . ?
O3 C19 C16 C17 92.2(5) . . . . ?
C20 C19 C16 C17 -88.1(5) . . . . ?
O2 C17 C16 C15 -99.4(5) . . . . ?
C18 C17 C16 C15 78.4(5) . . . . ?
O2 C17 C16 C19 135.3(4) . . . . ?
C18 C17 C16 C19 -46.9(6) . . . . ?
C16 C15 C14 C13 -158.3(3) . . . . ?
C9 C15 C14 C13 -31.8(4) . . . . ?
C8 C9 C10 C11 -25.1(4) . . . . ?
C15 C9 C10 C11 -152.4(3) . . . . ?
C12 C9 C10 C11 92.8(4) . . . . ?
C8 N2 C11 C10 -14.4(4) . . . . ?
C7 N2 C11 C10 167.5(3) . . . . ?
C9 C10 C11 N2 24.2(4) . . . . ?
C8 C9 C12 C13 -161.4(3) . . . . ?
C15 C9 C12 C13 -38.3(4) . . . . ?
C10 C9 C12 C13 85.4(4) . . . . ?
C9 C12 C13 C14 19.0(5) . . . . ?
C15 C14 C13 C12 8.1(5) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.68
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.037
