# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc1np6g0
_database_code_depnum_ccdc_archive 'CCDC 1539722'
_audit_update_record             
;
2017-03-23 deposited with the CCDC.
2017-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 Cl N O'
_chemical_formula_weight         261.74

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                   8.6226(12)
_cell_length_b                   13.6329(18)
_cell_length_c                   22.798(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2680.0(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    8686
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9475
_exptl_absorpt_correction_T_max  0.9680
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 5.814
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            29367
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         27.51
_reflns_number_total             6127
_reflns_number_gt                5762
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'

_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)+(0.0485P)²+0.0402P] 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   0.01(3)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         6127
_refine_ls_number_parameters     331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0248
_refine_ls_wR_factor_ref         0.0696
_refine_ls_wR_factor_gt          0.0685
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.002
_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 0.50832(3) 0.04524(2) 0.822510(12) 0.02931(7) Uani 1 1 d . . .
Cl2 Cl 0.56506(5) -0.16162(3) 0.594109(15) 0.04461(10) Uani 1 1 d . . .
O1 O -0.02283(11) 0.21420(6) 0.51750(4) 0.0317(2) Uani 1 1 d . . .
O2 O 0.95810(14) 0.35795(6) 0.75187(4) 0.0411(3) Uani 1 1 d . . .
N1 N 0.20158(12) 0.25129(7) 0.62912(5) 0.0243(2) Uani 1 1 d . . .
N2 N 0.75185(13) 0.23572(8) 0.65947(5) 0.0286(2) Uani 1 1 d . . .
C1 C 0.28319(14) 0.21544(8) 0.67646(5) 0.0221(2) Uani 1 1 d . . .
C2 C 0.37593(14) 0.26528(9) 0.71714(5) 0.0254(2) Uani 1 1 d . . .
H2 H 0.3911 0.3341 0.7144 0.030 Uiso 1 1 calc R . .
C3 C 0.44451(14) 0.21144(9) 0.76123(5) 0.0254(2) Uani 1 1 d . . .
H3 H 0.5082 0.2434 0.7894 0.031 Uiso 1 1 calc R . .
C4 C 0.42072(13) 0.10917(9) 0.76490(5) 0.0220(2) Uani 1 1 d . . .
C5 C 0.33050(13) 0.05827(8) 0.72542(5) 0.0204(2) Uani 1 1 d . . .
H5 H 0.3163 -0.0106 0.7287 0.024 Uiso 1 1 calc R . .
C6 C 0.26038(13) 0.11199(8) 0.68014(5) 0.0191(2) Uani 1 1 d . . .
C7 C 0.16118(13) 0.08704(8) 0.63251(5) 0.0198(2) Uani 1 1 d . . .
C8 C 0.08521(13) -0.00023(8) 0.60554(5) 0.0205(2) Uani 1 1 d . . .
H8A H 0.0161 -0.0335 0.6339 0.025 Uiso 1 1 calc R . .
H8B H 0.1632 -0.0477 0.5911 0.025 Uiso 1 1 calc R . .
C9 C -0.00904(13) 0.04473(8) 0.55399(5) 0.0208(2) Uani 1 1 d . . .
H9 H -0.1216 0.0367 0.5633 0.025 Uiso 1 1 calc R . .
C10 C 0.02679(13) 0.15562(9) 0.55333(5) 0.0227(2) Uani 1 1 d . . .
C11 C 0.12843(13) 0.17216(8) 0.60327(5) 0.0215(2) Uani 1 1 d . . .
C12 C 0.19261(18) 0.35328(9) 0.61098(7) 0.0353(3) Uani 1 1 d . . .
H12A H 0.1339 0.3908 0.6402 0.053 Uiso 1 1 calc R . .
H12B H 0.1404 0.3575 0.5729 0.053 Uiso 1 1 calc R . .
H12C H 0.2975 0.3803 0.6076 0.053 Uiso 1 1 calc R . .
C13 C 0.01974(14) -0.00162(9) 0.49350(5) 0.0245(2) Uani 1 1 d . . .
H13 H -0.0351 0.0398 0.4638 0.029 Uiso 1 1 calc R . .
C14 C 0.19090(15) -0.00241(10) 0.47728(5) 0.0305(3) Uani 1 1 d . . .
H14A H 0.2447 -0.0526 0.5003 0.046 Uiso 1 1 calc R . .
H14B H 0.2362 0.0620 0.4856 0.046 Uiso 1 1 calc R . .
H14C H 0.2021 -0.0171 0.4354 0.046 Uiso 1 1 calc R . .
C15 C -0.04976(19) -0.10415(10) 0.49015(6) 0.0378(3) Uani 1 1 d . . .
H15A H -0.0311 -0.1317 0.4511 0.057 Uiso 1 1 calc R . .
H15B H -0.1616 -0.1006 0.4974 0.057 Uiso 1 1 calc R . .
H15C H -0.0012 -0.1461 0.5198 0.057 Uiso 1 1 calc R . .
C16 C 0.69196(14) 0.14840(9) 0.63973(5) 0.0265(3) Uani 1 1 d . . .
C17 C 0.59958(15) 0.13088(11) 0.59036(6) 0.0329(3) Uani 1 1 d . . .
H17 H 0.5651 0.1831 0.5661 0.039 Uiso 1 1 calc R . .
C18 C 0.56063(15) 0.03519(11) 0.57836(6) 0.0348(3) Uani 1 1 d . . .
H18 H 0.4983 0.0207 0.5451 0.042 Uiso 1 1 calc R . .
C19 C 0.61212(15) -0.04152(10) 0.61481(6) 0.0310(3) Uani 1 1 d . . .
C20 C 0.69983(14) -0.02623(9) 0.66435(5) 0.0249(2) Uani 1 1 d . . .
H20 H 0.7310 -0.0793 0.6887 0.030 Uiso 1 1 calc R . .
C21 C 0.74173(13) 0.07144(9) 0.67764(5) 0.0228(2) Uani 1 1 d . . .
C22 C 0.83410(14) 0.11690(8) 0.72174(5) 0.0206(2) Uani 1 1 d . . .
C23 C 0.92606(13) 0.09300(8) 0.77565(5) 0.0206(2) Uani 1 1 d . . .
H23A H 1.0070 0.0435 0.7672 0.025 Uiso 1 1 calc R . .
H23B H 0.8582 0.0683 0.8074 0.025 Uiso 1 1 calc R . .
C24 C 0.99936(14) 0.19344(8) 0.79234(5) 0.0219(2) Uani 1 1 d . . .
H24 H 1.1129 0.1885 0.7840 0.026 Uiso 1 1 calc R . .
C25 C 0.93292(16) 0.26974(9) 0.74989(5) 0.0265(3) Uani 1 1 d . . .
C26 C 0.83798(14) 0.21551(8) 0.70873(5) 0.0240(2) Uani 1 1 d . . .
C27 C 0.73864(18) 0.32978(10) 0.62975(6) 0.0388(3) Uani 1 1 d . . .
H27A H 0.7931 0.3267 0.5921 0.058 Uiso 1 1 calc R . .
H27B H 0.7849 0.3812 0.6542 0.058 Uiso 1 1 calc R . .
H27C H 0.6290 0.3448 0.6230 0.058 Uiso 1 1 calc R . .
C28 C 0.98278(14) 0.22545(8) 0.85676(5) 0.0232(2) Uani 1 1 d . . .
H28 H 1.0351 0.2906 0.8608 0.028 Uiso 1 1 calc R . .
C29 C 1.06647(18) 0.15412(10) 0.89716(6) 0.0378(3) Uani 1 1 d . . .
H29A H 1.0635 0.1791 0.9375 0.057 Uiso 1 1 calc R . .
H29B H 1.1746 0.1473 0.8845 0.057 Uiso 1 1 calc R . .
H29C H 1.0153 0.0900 0.8955 0.057 Uiso 1 1 calc R . .
C30 C 0.81330(14) 0.23932(9) 0.87438(6) 0.0282(3) Uani 1 1 d . . .
H30A H 0.7584 0.1766 0.8710 0.042 Uiso 1 1 calc R . .
H30B H 0.7647 0.2877 0.8484 0.042 Uiso 1 1 calc R . .
H30C H 0.8080 0.2626 0.9150 0.042 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 C4 1.7478(12) . ?
Cl2 C19 1.7516(14) . ?
O1 C10 1.2198(14) . ?
O2 C25 1.2228(15) . ?
N1 C1 1.3780(16) . ?
N1 C11 1.3816(15) . ?
N1 C12 1.4527(15) . ?
N2 C16 1.3734(17) . ?
N2 C26 1.3742(16) . ?
N2 C27 1.4548(15) . ?
C1 C2 1.4004(17) . ?
C1 C6 1.4264(15) . ?
C2 C3 1.3780(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.4118(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.3772(16) . ?
C5 C6 1.4026(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.4236(16) . ?
C7 C11 1.3679(16) . ?
C7 C8 1.4909(15) . ?
C8 C9 1.5546(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C13 1.5372(15) . ?
C9 C10 1.5431(16) . ?
C9 H9 1.0000 . ?
C10 C11 1.4544(16) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.5215(18) . ?
C13 C15 1.5227(19) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.3994(18) . ?
C16 C21 1.4255(17) . ?
C17 C18 1.375(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.408(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.3752(18) . ?
C20 C21 1.4125(17) . ?
C20 H20 0.9500 . ?
C21 C22 1.4246(17) . ?
C22 C26 1.3771(15) . ?
C22 C23 1.4985(16) . ?
C23 C24 1.5553(15) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.5319(16) . ?
C24 C28 1.5388(16) . ?
C24 H24 1.0000 . ?
C25 C26 1.4482(19) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.5214(17) . ?
C28 C30 1.5272(17) . ?
C28 H28 1.0000 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?

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
C1 N1 C11 106.88(9) . . ?
C1 N1 C12 126.13(11) . . ?
C11 N1 C12 126.98(11) . . ?
C16 N2 C26 107.29(10) . . ?
C16 N2 C27 125.58(11) . . ?
C26 N2 C27 126.85(12) . . ?
N1 C1 C2 129.66(11) . . ?
N1 C1 C6 109.05(10) . . ?
C2 C1 C6 121.30(11) . . ?
C3 C2 C1 118.02(11) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 120.45(11) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 122.75(11) . . ?
C5 C4 Cl1 118.95(9) . . ?
C3 C4 Cl1 118.30(9) . . ?
C4 C5 C6 117.48(10) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 H5 121.3 . . ?
C5 C6 C7 134.07(10) . . ?
C5 C6 C1 120.01(11) . . ?
C7 C6 C1 105.92(10) . . ?
C11 C7 C6 107.04(10) . . ?
C11 C7 C8 112.66(10) . . ?
C6 C7 C8 140.30(10) . . ?
C7 C8 C9 103.12(9) . . ?
C7 C8 H8A 111.1 . . ?
C9 C8 H8A 111.1 . . ?
C7 C8 H8B 111.1 . . ?
C9 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
C13 C9 C10 111.20(9) . . ?
C13 C9 C8 115.58(9) . . ?
C10 C9 C8 106.80(9) . . ?
C13 C9 H9 107.7 . . ?
C10 C9 H9 107.7 . . ?
C8 C9 H9 107.7 . . ?
O1 C10 C11 129.35(11) . . ?
O1 C10 C9 125.29(11) . . ?
C11 C10 C9 105.36(9) . . ?
C7 C11 N1 111.12(10) . . ?
C7 C11 C10 111.99(10) . . ?
N1 C11 C10 136.89(11) . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C15 111.29(11) . . ?
C14 C13 C9 112.18(10) . . ?
C15 C13 C9 111.02(10) . . ?
C14 C13 H13 107.4 . . ?
C15 C13 H13 107.4 . . ?
C9 C13 H13 107.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 C17 128.72(11) . . ?
N2 C16 C21 109.03(11) . . ?
C17 C16 C21 122.23(12) . . ?
C18 C17 C16 117.46(12) . . ?
C18 C17 H17 121.3 . . ?
C16 C17 H17 121.3 . . ?
C17 C18 C19 120.70(12) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C20 C19 C18 123.07(13) . . ?
C20 C19 Cl2 119.36(11) . . ?
C18 C19 Cl2 117.54(11) . . ?
C19 C20 C21 117.37(12) . . ?
C19 C20 H20 121.3 . . ?
C21 C20 H20 121.3 . . ?
C20 C21 C22 134.79(11) . . ?
C20 C21 C16 119.13(11) . . ?
C22 C21 C16 106.02(10) . . ?
C26 C22 C21 106.63(11) . . ?
C26 C22 C23 112.09(11) . . ?
C21 C22 C23 141.27(10) . . ?
C22 C23 C24 102.96(9) . . ?
C22 C23 H23A 111.2 . . ?
C24 C23 H23A 111.2 . . ?
C22 C23 H23B 111.2 . . ?
C24 C23 H23B 111.2 . . ?
H23A C23 H23B 109.1 . . ?
C25 C24 C28 112.06(9) . . ?
C25 C24 C23 106.93(10) . . ?
C28 C24 C23 116.45(9) . . ?
C25 C24 H24 107.0 . . ?
C28 C24 H24 107.0 . . ?
C23 C24 H24 107.0 . . ?
O2 C25 C26 128.78(12) . . ?
O2 C25 C24 125.31(13) . . ?
C26 C25 C24 105.91(9) . . ?
N2 C26 C22 111.02(11) . . ?
N2 C26 C25 137.11(11) . . ?
C22 C26 C25 111.87(11) . . ?
N2 C27 H27A 109.5 . . ?
N2 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N2 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C30 111.95(11) . . ?
C29 C28 C24 110.63(10) . . ?
C30 C28 C24 112.03(10) . . ?
C29 C28 H28 107.3 . . ?
C30 C28 H28 107.3 . . ?
C24 C28 H28 107.3 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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
C11 N1 C1 C2 -179.73(12) . . . . ?
C12 N1 C1 C2 -0.8(2) . . . . ?
C11 N1 C1 C6 0.00(13) . . . . ?
C12 N1 C1 C6 178.91(12) . . . . ?
N1 C1 C2 C3 179.45(11) . . . . ?
C6 C1 C2 C3 -0.25(17) . . . . ?
C1 C2 C3 C4 -0.17(17) . . . . ?
C2 C3 C4 C5 0.37(18) . . . . ?
C2 C3 C4 Cl1 -178.99(9) . . . . ?
C3 C4 C5 C6 -0.11(17) . . . . ?
Cl1 C4 C5 C6 179.24(8) . . . . ?
C4 C5 C6 C7 -179.54(12) . . . . ?
C4 C5 C6 C1 -0.31(16) . . . . ?
N1 C1 C6 C5 -179.26(10) . . . . ?
C2 C1 C6 C5 0.51(17) . . . . ?
N1 C1 C6 C7 0.16(13) . . . . ?
C2 C1 C6 C7 179.93(10) . . . . ?
C5 C6 C7 C11 179.03(12) . . . . ?
C1 C6 C7 C11 -0.27(12) . . . . ?
C5 C6 C7 C8 -1.3(2) . . . . ?
C1 C6 C7 C8 179.44(13) . . . . ?
C11 C7 C8 C9 -1.96(12) . . . . ?
C6 C7 C8 C9 178.34(13) . . . . ?
C7 C8 C9 C13 127.04(10) . . . . ?
C7 C8 C9 C10 2.76(11) . . . . ?
C13 C9 C10 O1 50.51(15) . . . . ?
C8 C9 C10 O1 177.44(11) . . . . ?
C13 C9 C10 C11 -129.60(10) . . . . ?
C8 C9 C10 C11 -2.67(11) . . . . ?
C6 C7 C11 N1 0.29(13) . . . . ?
C8 C7 C11 N1 -179.51(9) . . . . ?
C6 C7 C11 C10 -179.91(9) . . . . ?
C8 C7 C11 C10 0.29(14) . . . . ?
C1 N1 C11 C7 -0.18(13) . . . . ?
C12 N1 C11 C7 -179.07(12) . . . . ?
C1 N1 C11 C10 -179.92(13) . . . . ?
C12 N1 C11 C10 1.2(2) . . . . ?
O1 C10 C11 C7 -178.57(12) . . . . ?
C9 C10 C11 C7 1.54(12) . . . . ?
O1 C10 C11 N1 1.2(2) . . . . ?
C9 C10 C11 N1 -178.72(13) . . . . ?
C10 C9 C13 C14 67.81(13) . . . . ?
C8 C9 C13 C14 -54.15(14) . . . . ?
C10 C9 C13 C15 -166.98(10) . . . . ?
C8 C9 C13 C15 71.07(13) . . . . ?
C26 N2 C16 C17 -178.54(12) . . . . ?
C27 N2 C16 C17 -4.3(2) . . . . ?
C26 N2 C16 C21 0.05(13) . . . . ?
C27 N2 C16 C21 174.29(11) . . . . ?
N2 C16 C17 C18 176.79(12) . . . . ?
C21 C16 C17 C18 -1.63(18) . . . . ?
C16 C17 C18 C19 0.18(19) . . . . ?
C17 C18 C19 C20 1.4(2) . . . . ?
C17 C18 C19 Cl2 -176.87(10) . . . . ?
C18 C19 C20 C21 -1.48(18) . . . . ?
Cl2 C19 C20 C21 176.78(9) . . . . ?
C19 C20 C21 C22 -176.72(12) . . . . ?
C19 C20 C21 C16 0.02(16) . . . . ?
N2 C16 C21 C20 -177.15(10) . . . . ?
C17 C16 C21 C20 1.55(17) . . . . ?
N2 C16 C21 C22 0.45(12) . . . . ?
C17 C16 C21 C22 179.15(11) . . . . ?
C20 C21 C22 C26 176.27(12) . . . . ?
C16 C21 C22 C26 -0.77(12) . . . . ?
C20 C21 C22 C23 -3.2(2) . . . . ?
C16 C21 C22 C23 179.71(14) . . . . ?
C26 C22 C23 C24 -3.86(12) . . . . ?
C21 C22 C23 C24 175.64(14) . . . . ?
C22 C23 C24 C25 4.81(11) . . . . ?
C22 C23 C24 C28 130.97(10) . . . . ?
C28 C24 C25 O2 47.11(17) . . . . ?
C23 C24 C25 O2 175.84(12) . . . . ?
C28 C24 C25 C26 -132.99(10) . . . . ?
C23 C24 C25 C26 -4.25(12) . . . . ?
C16 N2 C26 C22 -0.57(13) . . . . ?
C27 N2 C26 C22 -174.71(11) . . . . ?
C16 N2 C26 C25 178.35(14) . . . . ?
C27 N2 C26 C25 4.2(2) . . . . ?
C21 C22 C26 N2 0.84(13) . . . . ?
C23 C22 C26 N2 -179.48(9) . . . . ?
C21 C22 C26 C25 -178.36(10) . . . . ?
C23 C22 C26 C25 1.31(14) . . . . ?
O2 C25 C26 N2 2.9(2) . . . . ?
C24 C25 C26 N2 -176.97(13) . . . . ?
O2 C25 C26 C22 -178.16(13) . . . . ?
C24 C25 C26 C22 1.94(13) . . . . ?
C25 C24 C28 C29 -173.33(11) . . . . ?
C23 C24 C28 C29 63.12(14) . . . . ?
C25 C24 C28 C30 60.99(13) . . . . ?
C23 C24 C28 C30 -62.56(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.033
