# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_audit_block_doi                 10.5517/cc1kpyry
_database_code_depnum_ccdc_archive 'CCDC 1451071'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        3ca'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_absolute_configuration ' unk '
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 Cl N2 O2'
_chemical_formula_weight         350.79

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   7.1740(7)
_cell_length_b                   14.3271(14)
_cell_length_c                   17.4194(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1790.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3659
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      25.77

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9347
_exptl_absorpt_correction_T_max  0.9558
_exptl_absorpt_process_details   SADABS

_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 APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9147
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3155
_reflns_number_gt                2865
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0240P)²+0.3449P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_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   -0.01(5)
_refine_ls_number_reflns         3155
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0661
_refine_ls_wR_factor_gt          0.0632
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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 0.34495(7) 0.30425(4) 0.13896(3) 0.05440(14) Uani 1 1 d . . .
O1 O 0.57443(17) 0.15110(8) 0.41157(6) 0.0407(3) Uani 1 1 d . . .
O2 O 0.09517(19) 0.18086(12) 0.39283(8) 0.0702(4) Uani 1 1 d . . .
N1 N 0.3079(2) 0.08313(12) 0.45329(9) 0.0497(4) Uani 1 1 d . . .
N2 N 0.7489(4) 0.01747(17) 0.26006(15) 0.1015(8) Uani 1 1 d . . .
C1 C 0.5600(2) 0.31097(12) 0.18511(9) 0.0401(4) Uani 1 1 d . . .
C2 C 0.6979(3) 0.36346(13) 0.15025(12) 0.0530(5) Uani 1 1 d . . .
H2 H 0.6740 0.3942 0.1043 0.064 Uiso 1 1 calc R . .
C3 C 0.8706(3) 0.36982(15) 0.18413(13) 0.0592(6) Uani 1 1 d . . .
H3 H 0.9639 0.4055 0.1614 0.071 Uiso 1 1 calc R . .
C4 C 0.9047(3) 0.32343(14) 0.25146(13) 0.0576(5) Uani 1 1 d . . .
H4 H 1.0215 0.3276 0.2743 0.069 Uiso 1 1 calc R . .
C5 C 0.7667(3) 0.27051(14) 0.28565(11) 0.0489(5) Uani 1 1 d . . .
H5 H 0.7930 0.2385 0.3308 0.059 Uiso 1 1 calc R . .
C6 C 0.5897(2) 0.26414(11) 0.25386(10) 0.0388(4) Uani 1 1 d . . .
C7 C 0.4360(2) 0.20640(12) 0.29003(9) 0.0387(4) Uani 1 1 d . . .
H7 H 0.3188 0.2343 0.2724 0.046 Uiso 1 1 calc R . .
C8 C 0.4376(3) 0.10726(14) 0.25814(11) 0.0497(5) Uani 1 1 d . . .
C9 C 0.6109(4) 0.05687(15) 0.25930(12) 0.0633(6) Uani 1 1 d . . .
C10 C 0.2889(4) 0.06712(18) 0.22790(14) 0.0798(8) Uani 1 1 d . . .
H10A H 0.2973 0.0071 0.2078 0.096 Uiso 1 1 calc R . .
H10B H 0.1758 0.0989 0.2267 0.096 Uiso 1 1 calc R . .
C11 C 0.4273(2) 0.20841(12) 0.37836(9) 0.0414(4) Uani 1 1 d . . .
C12 C 0.4368(3) 0.30596(14) 0.41224(12) 0.0597(5) Uani 1 1 d . . .
H12A H 0.4208 0.3026 0.4669 0.090 Uiso 1 1 calc R . .
H12B H 0.3397 0.3438 0.3905 0.090 Uiso 1 1 calc R . .
H12C H 0.5558 0.3332 0.4007 0.090 Uiso 1 1 calc R . .
C13 C 0.2535(3) 0.15807(15) 0.40744(11) 0.0493(5) Uani 1 1 d . . .
C14 C 0.4884(3) 0.08358(13) 0.45213(10) 0.0397(4) Uani 1 1 d . . .
C15 C 0.6084(3) 0.01565(12) 0.48970(9) 0.0406(4) Uani 1 1 d . . .
C16 C 0.7975(3) 0.01244(13) 0.47376(11) 0.0461(5) Uani 1 1 d . . .
H16 H 0.8502 0.0553 0.4400 0.055 Uiso 1 1 calc R . .
C17 C 0.9066(3) -0.05428(15) 0.50800(12) 0.0579(5) Uani 1 1 d . . .
H17 H 1.0338 -0.0562 0.4980 0.069 Uiso 1 1 calc R . .
C18 C 0.8283(4) -0.11817(17) 0.55704(13) 0.0718(7) Uani 1 1 d . . .
H18 H 0.9029 -0.1637 0.5795 0.086 Uiso 1 1 calc R . .
C19 C 0.6421(4) -0.11564(17) 0.57329(13) 0.0744(7) Uani 1 1 d . . .
H19 H 0.5909 -0.1590 0.6070 0.089 Uiso 1 1 calc R . .
C20 C 0.5300(3) -0.04897(15) 0.53991(11) 0.0577(6) Uani 1 1 d . . .
H20 H 0.4031 -0.0471 0.5508 0.069 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 C1 1.7423(18) . ?
O1 C14 1.348(2) . ?
O1 C11 1.457(2) . ?
O2 C13 1.209(2) . ?
N1 C14 1.295(2) . ?
N1 C13 1.394(2) . ?
N2 C9 1.140(3) . ?
C1 C2 1.383(3) . ?
C1 C6 1.389(2) . ?
C2 C3 1.376(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.516(2) . ?
C7 C8 1.525(3) . ?
C7 C11 1.540(2) . ?
C7 H7 0.9800 . ?
C8 C10 1.322(3) . ?
C8 C9 1.437(3) . ?
C10 H10A 0.9300 . ?
C10 H10B 0.9300 . ?
C11 C12 1.519(3) . ?
C11 C13 1.527(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 C15 1.455(3) . ?
C15 C16 1.386(3) . ?
C15 C20 1.392(3) . ?
C16 C17 1.372(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.366(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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 O1 C11 106.30(13) . . ?
C14 N1 C13 105.49(16) . . ?
C2 C1 C6 122.10(17) . . ?
C2 C1 Cl1 117.44(14) . . ?
C6 C1 Cl1 120.47(14) . . ?
C3 C2 C1 119.47(18) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 119.72(19) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 121.27(18) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 116.91(16) . . ?
C5 C6 C7 122.38(16) . . ?
C1 C6 C7 120.68(16) . . ?
C6 C7 C8 110.57(15) . . ?
C6 C7 C11 115.76(15) . . ?
C8 C7 C11 112.43(14) . . ?
C6 C7 H7 105.7 . . ?
C8 C7 H7 105.7 . . ?
C11 C7 H7 105.7 . . ?
C10 C8 C9 119.0(2) . . ?
C10 C8 C7 123.0(2) . . ?
C9 C8 C7 117.99(19) . . ?
N2 C9 C8 179.5(3) . . ?
C8 C10 H10A 120.0 . . ?
C8 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
O1 C11 C12 109.39(15) . . ?
O1 C11 C13 101.17(13) . . ?
C12 C11 C13 110.01(16) . . ?
O1 C11 C7 110.90(14) . . ?
C12 C11 C7 113.80(15) . . ?
C13 C11 C7 110.83(15) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 N1 126.28(19) . . ?
O2 C13 C11 124.75(18) . . ?
N1 C13 C11 108.98(15) . . ?
N1 C14 O1 118.03(17) . . ?
N1 C14 C15 125.55(18) . . ?
O1 C14 C15 116.41(15) . . ?
C16 C15 C20 119.95(18) . . ?
C16 C15 C14 120.77(17) . . ?
C20 C15 C14 119.23(18) . . ?
C17 C16 C15 119.64(19) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 120.7(2) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 120.1(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 119.4(2) . . ?
C19 C20 H20 120.3 . . ?
C15 C20 H20 120.3 . . ?

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
C6 C1 C2 C3 0.1(3) . . . . ?
Cl1 C1 C2 C3 -179.21(16) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C1 1.9(3) . . . . ?
C4 C5 C6 C7 179.83(18) . . . . ?
C2 C1 C6 C5 -1.4(3) . . . . ?
Cl1 C1 C6 C5 177.91(13) . . . . ?
C2 C1 C6 C7 -179.35(16) . . . . ?
Cl1 C1 C6 C7 0.0(2) . . . . ?
C5 C6 C7 C8 -90.8(2) . . . . ?
C1 C6 C7 C8 86.99(19) . . . . ?
C5 C6 C7 C11 38.5(2) . . . . ?
C1 C6 C7 C11 -143.70(16) . . . . ?
C6 C7 C8 C10 -126.6(2) . . . . ?
C11 C7 C8 C10 102.4(2) . . . . ?
C6 C7 C8 C9 51.6(2) . . . . ?
C11 C7 C8 C9 -79.5(2) . . . . ?
C10 C8 C9 N2 137(100) . . . . ?
C7 C8 C9 N2 -41(34) . . . . ?
C14 O1 C11 C12 115.11(16) . . . . ?
C14 O1 C11 C13 -0.95(16) . . . . ?
C14 O1 C11 C7 -118.57(15) . . . . ?
C6 C7 C11 O1 -75.58(18) . . . . ?
C8 C7 C11 O1 52.8(2) . . . . ?
C6 C7 C11 C12 48.3(2) . . . . ?
C8 C7 C11 C12 176.66(16) . . . . ?
C6 C7 C11 C13 172.87(14) . . . . ?
C8 C7 C11 C13 -58.7(2) . . . . ?
C14 N1 C13 O2 178.9(2) . . . . ?
C14 N1 C13 C11 -1.5(2) . . . . ?
O1 C11 C13 O2 -178.9(2) . . . . ?
C12 C11 C13 O2 65.5(3) . . . . ?
C7 C11 C13 O2 -61.2(3) . . . . ?
O1 C11 C13 N1 1.52(18) . . . . ?
C12 C11 C13 N1 -114.08(17) . . . . ?
C7 C11 C13 N1 119.19(17) . . . . ?
C13 N1 C14 O1 0.9(2) . . . . ?
C13 N1 C14 C15 -177.54(17) . . . . ?
C11 O1 C14 N1 0.1(2) . . . . ?
C11 O1 C14 C15 178.70(14) . . . . ?
N1 C14 C15 C16 168.30(19) . . . . ?
O1 C14 C15 C16 -10.2(2) . . . . ?
N1 C14 C15 C20 -9.2(3) . . . . ?
O1 C14 C15 C20 172.29(16) . . . . ?
C20 C15 C16 C17 -0.3(3) . . . . ?
C14 C15 C16 C17 -177.83(17) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C16 C17 C18 C19 -0.9(4) . . . . ?
C17 C18 C19 C20 0.5(4) . . . . ?
C18 C19 C20 C15 -0.1(4) . . . . ?
C16 C15 C20 C19 0.0(3) . . . . ?
C14 C15 C20 C19 177.52(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_zhugm_1217_2
_database_code_depnum_ccdc_archive 'CCDC 1451084'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-05-19 downloaded from the CCDC.
;
_audit_creation_date             2015-12-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        'SN2 '
_chemical_formula_moiety         'C21 H18 Cl N O4'
_chemical_formula_sum            'C21 H18 Cl N O4'
_chemical_formula_weight         383.81
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   7.1668(4)
_cell_length_b                   12.4455(8)
_cell_length_c                   21.2096(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1891.78(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1258
_cell_measurement_temperature    273.77(10)
_cell_measurement_theta_max      22.6230
_cell_measurement_theta_min      4.0380
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5160
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.42
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      273.77(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -9.00   17.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5229  -99.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega   36.00   98.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.2104 -178.0000  150.0000 62

#__ type_ start__ end____ width___ exp.time_
  3 omega   27.00   91.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.2104   77.0000 -120.0000 64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0933594000
_diffrn_orient_matrix_UB_12      0.0147314000
_diffrn_orient_matrix_UB_13      0.0069771000
_diffrn_orient_matrix_UB_21      -0.0240816000
_diffrn_orient_matrix_UB_22      -0.0064023000
_diffrn_orient_matrix_UB_23      -0.0321996000
_diffrn_orient_matrix_UB_31      -0.0222963000
_diffrn_orient_matrix_UB_32      -0.0547189000
_diffrn_orient_matrix_UB_33      0.0056356000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2476
_reflns_number_total             3555
_reflns_odcompleteness_completeness 99.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(9)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3555
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0538
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0378P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1143
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.66797(14) 0.10948(7) 0.09796(4) 0.0684(3) Uani 1 d . . .
O1 O 0.2536(3) -0.08357(15) 0.19609(8) 0.0462(5) Uani 1 d . . .
O2 O 0.2458(4) 0.02756(19) 0.34645(11) 0.0802(8) Uani 1 d . . .
O3 O 0.7503(4) 0.09258(18) 0.31094(9) 0.0703(7) Uani 1 d . . .
O4 O 0.6783(4) -0.0439(2) 0.37458(10) 0.0822(8) Uani 1 d . . .
N1 N 0.2125(4) 0.07958(19) 0.24177(12) 0.0527(7) Uani 1 d . . .
C1 C 0.6668(4) -0.0300(2) 0.09317(14) 0.0495(8) Uani 1 d . . .
C2 C 0.6473(6) -0.0770(3) 0.03497(15) 0.0744(12) Uani 1 d . . .
H2 H 0.6330 -0.0349 -0.0009 0.089 Uiso 1 calc . . R
C3 C 0.6493(8) -0.1876(3) 0.03044(16) 0.0906(15) Uani 1 d . . .
H3 H 0.6346 -0.2204 -0.0086 0.109 Uiso 1 calc . . R
C4 C 0.6728(6) -0.2491(3) 0.08336(16) 0.0794(12) Uani 1 d . . .
H4 H 0.6772 -0.3236 0.0799 0.095 Uiso 1 calc . . R
C5 C 0.6898(5) -0.2017(3) 0.14121(14) 0.0589(9) Uani 1 d . . .
H5 H 0.7051 -0.2446 0.1767 0.071 Uiso 1 calc . . R
C6 C 0.6848(4) -0.0905(2) 0.14820(13) 0.0443(7) Uani 1 d . . .
C7 C 0.7061(4) -0.0381(2) 0.20981(13) 0.0443(7) Uani 1 d . . .
H7 H 0.7868 0.0204 0.2110 0.053 Uiso 1 calc . . R
C8 C 0.6249(4) -0.0635(2) 0.26420(13) 0.0432(8) Uani 1 d . . .
C9 C 0.6842(5) -0.0053(3) 0.32263(14) 0.0527(8) Uani 1 d . . .
C10 C 0.8192(6) 0.1513(3) 0.36504(15) 0.0835(13) Uani 1 d . . .
H10A H 0.8595 0.2214 0.3520 0.125 Uiso 1 calc . . GR
H10B H 0.9224 0.1132 0.3833 0.125 Uiso 1 calc . . GR
H10C H 0.7214 0.1582 0.3957 0.125 Uiso 1 calc . . GR
C11 C 0.4753(4) -0.1465(3) 0.27469(14) 0.0489(8) Uani 1 d . . .
H11A H 0.4844 -0.1727 0.3177 0.059 Uiso 1 calc . . R
H11B H 0.4979 -0.2068 0.2467 0.059 Uiso 1 calc . . R
C12 C 0.2774(4) -0.1050(2) 0.26351(12) 0.0444(7) Uani 1 d . . .
C13 C 0.1308(5) -0.1837(3) 0.28541(16) 0.0646(10) Uani 1 d . . .
H13A H 0.0114 -0.1630 0.2688 0.097 Uiso 1 calc . . GR
H13B H 0.1257 -0.1836 0.3306 0.097 Uiso 1 calc . . GR
H13C H 0.1619 -0.2544 0.2707 0.097 Uiso 1 calc . . GR
C14 C 0.2448(5) 0.0067(3) 0.29069(16) 0.0563(9) Uani 1 d . . .
C15 C 0.2189(4) 0.0229(2) 0.19063(14) 0.0442(7) Uani 1 d . . .
C16 C 0.1896(4) 0.0621(2) 0.12658(15) 0.0476(8) Uani 1 d . . .
C17 C 0.1652(6) -0.0071(3) 0.07680(16) 0.0686(11) Uani 1 d . . .
H17 H 0.1679 -0.0810 0.0834 0.082 Uiso 1 calc . . R
C18 C 0.1365(7) 0.0337(3) 0.01662(17) 0.0895(14) Uani 1 d . . .
H18 H 0.1183 -0.0127 -0.0172 0.107 Uiso 1 calc . . R
C19 C 0.1353(7) 0.1435(4) 0.00714(19) 0.0877(13) Uani 1 d . . .
H19 H 0.1167 0.1706 -0.0332 0.105 Uiso 1 calc . . R
C20 C 0.1610(6) 0.2127(3) 0.05613(18) 0.0726(11) Uani 1 d . . .
H20 H 0.1616 0.2865 0.0491 0.087 Uiso 1 calc . . R
C21 C 0.1860(5) 0.1731(3) 0.11593(16) 0.0559(9) Uani 1 d . . .
H21 H 0.2007 0.2202 0.1496 0.067 Uiso 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 C1 1.739(3) . ?
O1 C12 1.464(3) . ?
O1 C15 1.353(3) . ?
O2 C14 1.211(4) . ?
O3 C9 1.330(4) . ?
O3 C10 1.447(3) . ?
O4 C9 1.203(3) . ?
N1 C14 1.397(4) . ?
N1 C15 1.295(3) . ?
C1 C2 1.373(4) . ?
C1 C6 1.395(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.369(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.367(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(4) . ?
C6 C7 1.468(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.330(4) . ?
C8 C9 1.497(4) . ?
C8 C11 1.505(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.528(4) . ?
C12 C13 1.510(4) . ?
C12 C14 1.523(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 C16 1.459(4) . ?
C16 C17 1.374(4) . ?
C16 C21 1.399(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.362(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.373(4) . ?
C21 H21 0.9300 . ?

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
C15 O1 C12 106.4(2) . . ?
C9 O3 C10 115.8(3) . . ?
C15 N1 C14 105.2(3) . . ?
C2 C1 Cl1 118.6(3) . . ?
C2 C1 C6 122.1(3) . . ?
C6 C1 Cl1 119.3(2) . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.1(3) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.5(3) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C7 121.0(3) . . ?
C5 C6 C1 116.7(3) . . ?
C5 C6 C7 122.2(3) . . ?
C6 C7 H7 115.8 . . ?
C8 C7 C6 128.4(3) . . ?
C8 C7 H7 115.8 . . ?
C7 C8 C9 118.6(3) . . ?
C7 C8 C11 127.1(3) . . ?
C9 C8 C11 114.3(3) . . ?
O3 C9 C8 112.9(3) . . ?
O4 C9 O3 123.3(3) . . ?
O4 C9 C8 123.7(3) . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 108.8 . . ?
C8 C11 H11B 108.8 . . ?
C8 C11 C12 113.9(2) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
O1 C12 C11 108.7(2) . . ?
O1 C12 C13 109.7(2) . . ?
O1 C12 C14 100.7(2) . . ?
C13 C12 C11 112.3(2) . . ?
C13 C12 C14 111.7(3) . . ?
C14 C12 C11 113.1(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 N1 126.0(3) . . ?
O2 C14 C12 124.4(3) . . ?
N1 C14 C12 109.7(3) . . ?
O1 C15 C16 115.7(3) . . ?
N1 C15 O1 117.9(3) . . ?
N1 C15 C16 126.3(3) . . ?
C17 C16 C15 121.6(3) . . ?
C17 C16 C21 119.5(3) . . ?
C21 C16 C15 118.9(3) . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.7(3) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(4) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 120.9(4) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 120.2 . . ?
C19 C20 C21 119.7(3) . . ?
C21 C20 H20 120.2 . . ?
C16 C21 H21 119.8 . . ?
C20 C21 C16 120.4(3) . . ?
C20 C21 H21 119.8 . . ?

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
Cl1 C1 C2 C3 178.9(4) . . . . ?
Cl1 C1 C6 C5 -177.7(3) . . . . ?
Cl1 C1 C6 C7 -0.5(4) . . . . ?
O1 C12 C14 O2 177.9(3) . . . . ?
O1 C12 C14 N1 -1.5(3) . . . . ?
O1 C15 C16 C17 11.3(5) . . . . ?
O1 C15 C16 C21 -168.8(3) . . . . ?
N1 C15 C16 C17 -167.8(3) . . . . ?
N1 C15 C16 C21 12.2(5) . . . . ?
C1 C2 C3 C4 -0.8(8) . . . . ?
C1 C6 C7 C8 137.3(3) . . . . ?
C2 C1 C6 C5 2.5(5) . . . . ?
C2 C1 C6 C7 179.8(3) . . . . ?
C2 C3 C4 C5 1.6(8) . . . . ?
C3 C4 C5 C6 -0.3(7) . . . . ?
C4 C5 C6 C1 -1.7(6) . . . . ?
C4 C5 C6 C7 -178.9(3) . . . . ?
C5 C6 C7 C8 -45.6(5) . . . . ?
C6 C1 C2 C3 -1.3(7) . . . . ?
C6 C7 C8 C9 173.5(3) . . . . ?
C6 C7 C8 C11 -6.5(5) . . . . ?
C7 C8 C9 O3 26.8(4) . . . . ?
C7 C8 C9 O4 -151.0(3) . . . . ?
C7 C8 C11 C12 -85.8(4) . . . . ?
C8 C11 C12 O1 68.6(3) . . . . ?
C8 C11 C12 C13 -169.9(3) . . . . ?
C8 C11 C12 C14 -42.4(3) . . . . ?
C9 C8 C11 C12 94.2(3) . . . . ?
C10 O3 C9 O4 0.9(5) . . . . ?
C10 O3 C9 C8 -176.9(3) . . . . ?
C11 C8 C9 O3 -153.2(3) . . . . ?
C11 C8 C9 O4 29.0(5) . . . . ?
C11 C12 C14 O2 -66.3(4) . . . . ?
C11 C12 C14 N1 114.3(3) . . . . ?
C12 O1 C15 N1 -0.6(4) . . . . ?
C12 O1 C15 C16 -179.7(2) . . . . ?
C13 C12 C14 O2 61.5(5) . . . . ?
C13 C12 C14 N1 -117.9(3) . . . . ?
C14 N1 C15 O1 -0.4(4) . . . . ?
C14 N1 C15 C16 178.6(3) . . . . ?
C15 O1 C12 C11 -117.9(3) . . . . ?
C15 O1 C12 C13 119.0(3) . . . . ?
C15 O1 C12 C14 1.2(3) . . . . ?
C15 N1 C14 O2 -178.2(4) . . . . ?
C15 N1 C14 C12 1.2(4) . . . . ?
C15 C16 C17 C18 179.6(4) . . . . ?
C15 C16 C21 C20 179.2(3) . . . . ?
C16 C17 C18 C19 0.9(7) . . . . ?
C17 C16 C21 C20 -0.9(6) . . . . ?
C17 C18 C19 C20 -0.3(8) . . . . ?
C18 C19 C20 C21 -0.9(7) . . . . ?
C19 C20 C21 C16 1.5(6) . . . . ?
C21 C16 C17 C18 -0.3(6) . . . . ?

_olex2_date_sample_data_collection 2015-12-18
_olex2_submission_special_instructions 'No special instructions were received'
