# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_cd213616
_database_code_depnum_ccdc_archive 'CCDC 1412716'
_audit_update_record             
;
2015-07-14 deposited with the CCDC.
2015-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H32 N2 O4'
_chemical_formula_weight         388.50

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'

_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                   10.016(5)
_cell_length_b                   10.025(4)
_cell_length_c                   21.596(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2168.3(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5419
_cell_measurement_theta_min      4.480
_cell_measurement_theta_max      51.461

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.112
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.28969
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13090
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4271
_reflns_number_gt                3854
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0570P)²+0.1179P] 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   0.0(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4271
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0954
_refine_ls_wR_factor_gt          0.0918
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_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
N1 N 0.47237(13) 0.25144(13) 0.79354(5) 0.0448(3) Uani 1 1 d . . .
N2 N 0.33474(15) 0.40439(13) 0.99447(6) 0.0442(3) Uani 1 1 d . . .
O1 O 0.10032(11) 0.21409(11) 0.98705(5) 0.0505(3) Uani 1 1 d . . .
H1 H 0.1071 0.2782 1.0104 0.076 Uiso 1 1 calc R . .
O2 O 0.65962(13) 0.34438(13) 0.74801(5) 0.0665(3) Uani 1 1 d . . .
O3 O 0.14867(12) 0.45066(13) 1.05172(5) 0.0646(3) Uani 1 1 d . . .
O4 O 0.35531(11) 0.51354(11) 1.08241(5) 0.0518(3) Uani 1 1 d . . .
C1 C 0.27331(15) 0.35072(14) 0.93699(6) 0.0392(3) Uani 1 1 d . . .
C2 C 0.21464(15) 0.20901(14) 0.94695(6) 0.0414(3) Uani 1 1 d . . .
C3 C 0.16394(15) 0.16029(15) 0.88376(6) 0.0447(3) Uani 1 1 d . . .
H3 H 0.1230 0.0725 0.8900 0.054 Uiso 1 1 calc R . .
C4 C 0.05551(17) 0.25360(19) 0.85876(7) 0.0537(4) Uani 1 1 d . . .
H4A H 0.0272 0.2216 0.8185 0.064 Uiso 1 1 calc R . .
H4B H -0.0211 0.2498 0.8862 0.064 Uiso 1 1 calc R . .
C5 C 0.09985(17) 0.39864(17) 0.85256(7) 0.0514(4) Uani 1 1 d . . .
H5 H 0.1669 0.4040 0.8196 0.062 Uiso 1 1 calc R . .
C6 C 0.16401(17) 0.44644(16) 0.91312(7) 0.0474(3) Uani 1 1 d . . .
H6A H 0.0952 0.4551 0.9445 0.057 Uiso 1 1 calc R . .
H6B H 0.2029 0.5339 0.9066 0.057 Uiso 1 1 calc R . .
C7 C -0.0172(2) 0.4879(2) 0.83501(9) 0.0757(6) Uani 1 1 d . . .
H7A H 0.0143 0.5772 0.8282 0.114 Uiso 1 1 calc R . .
H7B H -0.0816 0.4880 0.8679 0.114 Uiso 1 1 calc R . .
H7C H -0.0581 0.4548 0.7979 0.114 Uiso 1 1 calc R . .
C8 C 0.28085(17) 0.14218(16) 0.83871(7) 0.0492(4) Uani 1 1 d . . .
H8A H 0.3250 0.0584 0.8480 0.059 Uiso 1 1 calc R . .
H8B H 0.2457 0.1360 0.7970 0.059 Uiso 1 1 calc R . .
C9 C 0.38217(15) 0.25172(14) 0.84067(6) 0.0407(3) Uani 1 1 d . . .
C10 C 0.38426(14) 0.34647(14) 0.88761(6) 0.0393(3) Uani 1 1 d . . .
C11 C 0.48284(17) 0.44413(15) 0.88486(7) 0.0484(4) Uani 1 1 d . . .
H11 H 0.4858 0.5106 0.9149 0.058 Uiso 1 1 calc R . .
C12 C 0.57560(18) 0.44279(17) 0.83813(8) 0.0558(4) Uani 1 1 d . . .
H12 H 0.6430 0.5065 0.8363 0.067 Uiso 1 1 calc R . .
C13 C 0.56575(16) 0.34341(16) 0.79356(7) 0.0489(4) Uani 1 1 d . . .
C14 C 0.6463(2) 0.2505(2) 0.69892(7) 0.0695(5) Uani 1 1 d . . .
H14A H 0.5661 0.2688 0.6761 0.104 Uiso 1 1 calc R . .
H14B H 0.6419 0.1620 0.7158 0.104 Uiso 1 1 calc R . .
H14C H 0.7219 0.2573 0.6718 0.104 Uiso 1 1 calc R . .
C15 C 0.31612(16) 0.11393(16) 0.97632(7) 0.0483(4) Uani 1 1 d . . .
H15A H 0.3964 0.1133 0.9512 0.058 Uiso 1 1 calc R . .
H15B H 0.3401 0.1476 1.0169 0.058 Uiso 1 1 calc R . .
C16 C 0.2667(2) -0.02588(17) 0.98293(8) 0.0609(4) Uani 1 1 d . . .
H16 H 0.1815 -0.0377 0.9991 0.073 Uiso 1 1 calc R . .
C17 C 0.3330(3) -0.1321(2) 0.96793(10) 0.0863(7) Uani 1 1 d . . .
H17A H 0.4186 -0.1245 0.9516 0.104 Uiso 1 1 calc R . .
H17B H 0.2951 -0.2159 0.9735 0.104 Uiso 1 1 calc R . .
C18 C 0.26913(16) 0.45533(15) 1.04355(6) 0.0462(3) Uani 1 1 d . . .
C19 C 0.30859(18) 0.58116(16) 1.13944(7) 0.0523(4) Uani 1 1 d . . .
C20 C 0.2242(3) 0.6997(2) 1.12244(10) 0.0791(6) Uani 1 1 d . . .
H20A H 0.1431 0.6698 1.1033 0.119 Uiso 1 1 calc R . .
H20B H 0.2725 0.7556 1.0941 0.119 Uiso 1 1 calc R . .
H20C H 0.2032 0.7496 1.1591 0.119 Uiso 1 1 calc R . .
C21 C 0.4387(2) 0.6250(2) 1.16865(9) 0.0730(6) Uani 1 1 d . . .
H21A H 0.4881 0.6783 1.1397 0.110 Uiso 1 1 calc R . .
H21B H 0.4903 0.5479 1.1797 0.110 Uiso 1 1 calc R . .
H21C H 0.4203 0.6767 1.2051 0.110 Uiso 1 1 calc R . .
C22 C 0.2359(3) 0.4847(2) 1.18122(8) 0.0771(6) Uani 1 1 d . . .
H22A H 0.2877 0.4047 1.1855 0.116 Uiso 1 1 calc R . .
H22B H 0.1507 0.4634 1.1635 0.116 Uiso 1 1 calc R . .
H22C H 0.2233 0.5247 1.2212 0.116 Uiso 1 1 calc R . .
H2 H 0.416(2) 0.3910(17) 0.9999(8) 0.048(5) Uiso 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
N1 C13 1.313(2) . ?
N1 C9 1.3609(18) . ?
N2 C18 1.347(2) . ?
N2 C1 1.4862(19) . ?
N2 H2 0.828(19) . ?
O1 C2 1.4365(17) . ?
O1 H1 0.8200 . ?
O2 C13 1.3608(19) . ?
O2 C14 1.424(2) . ?
O3 C18 1.220(2) . ?
O4 C18 1.3379(18) . ?
O4 C19 1.4816(18) . ?
C1 C10 1.541(2) . ?
C1 C6 1.544(2) . ?
C1 C2 1.552(2) . ?
C2 C15 1.531(2) . ?
C2 C3 1.536(2) . ?
C3 C4 1.532(2) . ?
C3 C8 1.533(2) . ?
C3 H3 0.9800 . ?
C4 C5 1.526(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C7 1.523(3) . ?
C5 C6 1.534(2) . ?
C5 H5 0.9800 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.496(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.3893(19) . ?
C10 C11 1.392(2) . ?
C11 C12 1.372(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(2) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.493(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.296(3) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9300 . ?
C17 H17B 0.9300 . ?
C19 C20 1.504(3) . ?
C19 C22 1.509(3) . ?
C19 C21 1.513(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C13 N1 C9 118.11(13) . . ?
C18 N2 C1 126.32(14) . . ?
C18 N2 H2 115.3(12) . . ?
C1 N2 H2 117.6(12) . . ?
C2 O1 H1 109.5 . . ?
C13 O2 C14 117.95(14) . . ?
C18 O4 C19 121.14(13) . . ?
N2 C1 C10 106.83(12) . . ?
N2 C1 C6 110.32(12) . . ?
C10 C1 C6 107.30(11) . . ?
N2 C1 C2 111.86(11) . . ?
C10 C1 C2 110.10(11) . . ?
C6 C1 C2 110.27(12) . . ?
O1 C2 C15 107.55(11) . . ?
O1 C2 C3 106.46(12) . . ?
C15 C2 C3 112.93(12) . . ?
O1 C2 C1 110.66(11) . . ?
C15 C2 C1 112.07(12) . . ?
C3 C2 C1 107.05(11) . . ?
C4 C3 C8 112.96(13) . . ?
C4 C3 C2 110.69(13) . . ?
C8 C3 C2 110.43(13) . . ?
C4 C3 H3 107.5 . . ?
C8 C3 H3 107.5 . . ?
C2 C3 H3 107.5 . . ?
C5 C4 C3 113.98(14) . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C7 C5 C4 110.96(16) . . ?
C7 C5 C6 110.55(15) . . ?
C4 C5 C6 110.16(13) . . ?
C7 C5 H5 108.4 . . ?
C4 C5 H5 108.4 . . ?
C6 C5 H5 108.4 . . ?
C5 C6 C1 112.80(13) . . ?
C5 C6 H6A 109.0 . . ?
C1 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C1 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C3 114.41(12) . . ?
C9 C8 H8A 108.7 . . ?
C3 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C3 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N1 C9 C10 122.49(14) . . ?
N1 C9 C8 115.32(12) . . ?
C10 C9 C8 122.19(12) . . ?
C9 C10 C11 117.42(13) . . ?
C9 C10 C1 120.87(13) . . ?
C11 C10 C1 121.45(12) . . ?
C12 C11 C10 120.33(14) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 117.96(15) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
N1 C13 O2 119.79(14) . . ?
N1 C13 C12 123.67(14) . . ?
O2 C13 C12 116.54(14) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C2 113.84(14) . . ?
C16 C15 H15A 108.8 . . ?
C2 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C2 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C15 125.28(19) . . ?
C17 C16 H16 117.4 . . ?
C15 C16 H16 117.4 . . ?
C16 C17 H17A 120.0 . . ?
C16 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?
O3 C18 O4 124.32(14) . . ?
O3 C18 N2 125.55(14) . . ?
O4 C18 N2 110.12(14) . . ?
O4 C19 C20 109.65(14) . . ?
O4 C19 C22 110.86(14) . . ?
C20 C19 C22 112.41(18) . . ?
O4 C19 C21 101.97(14) . . ?
C20 C19 C21 110.85(16) . . ?
C22 C19 C21 110.62(16) . . ?
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 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C18 N2 C1 C10 162.38(14) . . . . ?
C18 N2 C1 C6 46.1(2) . . . . ?
C18 N2 C1 C2 -77.07(18) . . . . ?
N2 C1 C2 O1 68.53(15) . . . . ?
C10 C1 C2 O1 -172.84(11) . . . . ?
C6 C1 C2 O1 -54.63(14) . . . . ?
N2 C1 C2 C15 -51.50(15) . . . . ?
C10 C1 C2 C15 67.12(15) . . . . ?
C6 C1 C2 C15 -174.67(11) . . . . ?
N2 C1 C2 C3 -175.84(12) . . . . ?
C10 C1 C2 C3 -57.22(14) . . . . ?
C6 C1 C2 C3 60.99(14) . . . . ?
O1 C2 C3 C4 58.07(15) . . . . ?
C15 C2 C3 C4 175.87(13) . . . . ?
C1 C2 C3 C4 -60.32(15) . . . . ?
O1 C2 C3 C8 -176.07(12) . . . . ?
C15 C2 C3 C8 -58.28(16) . . . . ?
C1 C2 C3 C8 65.54(15) . . . . ?
C8 C3 C4 C5 -67.37(17) . . . . ?
C2 C3 C4 C5 57.05(17) . . . . ?
C3 C4 C5 C7 -173.15(14) . . . . ?
C3 C4 C5 C6 -50.39(18) . . . . ?
C7 C5 C6 C1 173.67(15) . . . . ?
C4 C5 C6 C1 50.67(19) . . . . ?
N2 C1 C6 C5 178.13(13) . . . . ?
C10 C1 C6 C5 62.10(16) . . . . ?
C2 C1 C6 C5 -57.82(16) . . . . ?
C4 C3 C8 C9 81.87(17) . . . . ?
C2 C3 C8 C9 -42.70(18) . . . . ?
C13 N1 C9 C10 1.2(2) . . . . ?
C13 N1 C9 C8 -178.44(14) . . . . ?
C3 C8 C9 N1 -167.98(13) . . . . ?
C3 C8 C9 C10 12.4(2) . . . . ?
N1 C9 C10 C11 0.5(2) . . . . ?
C8 C9 C10 C11 -179.92(14) . . . . ?
N1 C9 C10 C1 174.68(13) . . . . ?
C8 C9 C10 C1 -5.7(2) . . . . ?
N2 C1 C10 C9 150.44(13) . . . . ?
C6 C1 C10 C9 -91.25(15) . . . . ?
C2 C1 C10 C9 28.77(17) . . . . ?
N2 C1 C10 C11 -35.62(17) . . . . ?
C6 C1 C10 C11 82.69(16) . . . . ?
C2 C1 C10 C11 -157.28(13) . . . . ?
C9 C10 C11 C12 -1.8(2) . . . . ?
C1 C10 C11 C12 -175.90(14) . . . . ?
C10 C11 C12 C13 1.4(2) . . . . ?
C9 N1 C13 O2 178.43(13) . . . . ?
C9 N1 C13 C12 -1.6(2) . . . . ?
C14 O2 C13 N1 4.8(2) . . . . ?
C14 O2 C13 C12 -175.13(15) . . . . ?
C11 C12 C13 N1 0.4(3) . . . . ?
C11 C12 C13 O2 -179.67(15) . . . . ?
O1 C2 C15 C16 61.94(16) . . . . ?
C3 C2 C15 C16 -55.22(17) . . . . ?
C1 C2 C15 C16 -176.22(12) . . . . ?
C2 C15 C16 C17 133.6(2) . . . . ?
C19 O4 C18 O3 -1.3(2) . . . . ?
C19 O4 C18 N2 178.19(13) . . . . ?
C1 N2 C18 O3 9.5(3) . . . . ?
C1 N2 C18 O4 -170.03(13) . . . . ?
C18 O4 C19 C20 -64.7(2) . . . . ?
C18 O4 C19 C22 60.0(2) . . . . ?
C18 O4 C19 C21 177.81(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.828(19) 2.148(19) 2.940(2) 159.9(16) 4_557
O1 H1 N2 0.82 2.63 3.029(2) 111.6 .
O1 H1 O3 0.82 1.99 2.7946(18) 166.9 .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.028
####################################################################### 
# 
# 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_cd212638
_database_code_depnum_ccdc_archive 'CCDC 1412717'
_audit_update_record             
;
2015-07-14 deposited with the CCDC.
2015-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H25 Cl N2 O2'
_chemical_formula_weight         324.84

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           Orthorhombic
_symmetry_space_group_name_H-M   C222(1)

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

_cell_length_a                   10.351(3)
_cell_length_b                   11.942(3)
_cell_length_c                   26.963(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3333.0(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1513
_cell_measurement_theta_min      5.201
_cell_measurement_theta_max      40.079

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.121
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.056
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.52853
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9747
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_sigmaI/netI    0.0566
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3121
_reflns_number_gt                2455
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0556P)²+0.0000P] 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   -0.08(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3121
_refine_ls_number_parameters     213
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1165
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.047
_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 0.84872(8) 0.24984(8) 0.30999(3) 0.0472(2) Uani 1 1 d . . .
N1 N 0.8543(3) 0.1988(2) 0.19579(10) 0.0413(7) Uani 1 1 d D . .
N2 N 0.6891(3) 0.1884(3) 0.02910(9) 0.0443(7) Uani 1 1 d . . .
O1 O 0.6229(2) 0.3128(2) 0.22611(9) 0.0512(7) Uani 1 1 d D . .
O2 O 0.8114(2) 0.1130(2) -0.03383(8) 0.0556(7) Uani 1 1 d . . .
C1 C 0.6310(3) 0.2588(3) 0.17857(11) 0.0439(8) Uani 1 1 d . . .
C2 C 0.5892(3) 0.1375(3) 0.18328(13) 0.0508(9) Uani 1 1 d . . .
H2A H 0.5886 0.1033 0.1506 0.061 Uiso 1 1 calc R . .
H2B H 0.5017 0.1348 0.1962 0.061 Uiso 1 1 calc R . .
C3 C 0.6772(4) 0.0703(3) 0.21714(13) 0.0538(10) Uani 1 1 d . . .
H3A H 0.6704 0.0986 0.2508 0.065 Uiso 1 1 calc R . .
H3B H 0.6502 -0.0075 0.2172 0.065 Uiso 1 1 calc R . .
C4 C 0.8163(4) 0.0781(3) 0.19999(12) 0.0500(9) Uani 1 1 d . . .
H4A H 0.8722 0.0404 0.2235 0.060 Uiso 1 1 calc R . .
H4B H 0.8257 0.0416 0.1681 0.060 Uiso 1 1 calc R . .
C5 C 0.7728(3) 0.2675(3) 0.16065(10) 0.0332(7) Uani 1 1 d . . .
C6 C 0.8226(3) 0.3875(3) 0.16315(13) 0.0477(9) Uani 1 1 d . . .
H6A H 0.9108 0.3891 0.1510 0.057 Uiso 1 1 calc R . .
H6B H 0.8240 0.4112 0.1975 0.057 Uiso 1 1 calc R . .
C7 C 0.7419(4) 0.4709(3) 0.13324(16) 0.0644(12) Uani 1 1 d . . .
H7 H 0.7583 0.5442 0.1483 0.077 Uiso 1 1 calc R . .
C8 C 0.5967(4) 0.4480(4) 0.14121(17) 0.0712(13) Uani 1 1 d . . .
H8A H 0.5718 0.4825 0.1723 0.085 Uiso 1 1 calc R . .
H8B H 0.5497 0.4864 0.1151 0.085 Uiso 1 1 calc R . .
C9 C 0.5508(4) 0.3270(3) 0.14223(13) 0.0535(10) Uani 1 1 d . . .
H9 H 0.4614 0.3269 0.1542 0.064 Uiso 1 1 calc R . .
C10 C 0.5522(3) 0.2690(4) 0.09125(13) 0.0550(10) Uani 1 1 d . . .
H10A H 0.4903 0.2080 0.0917 0.066 Uiso 1 1 calc R . .
H10B H 0.5242 0.3223 0.0663 0.066 Uiso 1 1 calc R . .
C11 C 0.6817(3) 0.2234(3) 0.07652(11) 0.0395(8) Uani 1 1 d . . .
C12 C 0.7854(3) 0.2217(2) 0.10821(10) 0.0309(7) Uani 1 1 d . . .
C13 C 0.9044(3) 0.1879(3) 0.08909(11) 0.0350(7) Uani 1 1 d . . .
H13 H 0.9775 0.1891 0.1091 0.042 Uiso 1 1 calc R . .
C14 C 0.9135(3) 0.1532(3) 0.04115(11) 0.0431(8) Uani 1 1 d . . .
H14 H 0.9921 0.1309 0.0277 0.052 Uiso 1 1 calc R . .
C15 C 0.8004(4) 0.1522(3) 0.01300(11) 0.0424(8) Uani 1 1 d . . .
C16 C 0.6989(5) 0.1153(4) -0.06434(13) 0.0776(14) Uani 1 1 d . . .
H16A H 0.6305 0.0749 -0.0483 0.116 Uiso 1 1 calc R . .
H16B H 0.7179 0.0811 -0.0957 0.116 Uiso 1 1 calc R . .
H16C H 0.6727 0.1916 -0.0695 0.116 Uiso 1 1 calc R . .
C17 C 0.7819(5) 0.4825(4) 0.07917(18) 0.0807(14) Uani 1 1 d . . .
H17A H 0.7679 0.4127 0.0623 0.121 Uiso 1 1 calc R . .
H17B H 0.8717 0.5020 0.0774 0.121 Uiso 1 1 calc R . .
H17C H 0.7312 0.5401 0.0637 0.121 Uiso 1 1 calc R . .
H1A H 0.848(4) 0.227(3) 0.2250(8) 0.054(10) Uiso 1 1 d D . .
H2 H 0.934(2) 0.205(3) 0.1910(16) 0.076(14) Uiso 1 1 d D . .
H1 H 0.659(6) 0.300(5) 0.2515(14) 0.16(3) Uiso 1 1 d 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
N1 C4 1.499(5) . ?
N1 C5 1.511(4) . ?
N1 H1A 0.857(18) . ?
N1 H2 0.842(19) . ?
N2 C15 1.306(4) . ?
N2 C11 1.348(4) . ?
O1 C1 1.437(4) . ?
O1 H1 0.80(2) . ?
O2 C15 1.352(4) . ?
O2 C16 1.425(5) . ?
C1 C2 1.518(5) . ?
C1 C9 1.521(5) . ?
C1 C5 1.549(4) . ?
C2 C3 1.519(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.515(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C12 1.522(4) . ?
C5 C6 1.524(5) . ?
C6 C7 1.530(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C17 1.522(6) . ?
C7 C8 1.543(6) . ?
C7 H7 0.9800 . ?
C8 C9 1.521(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.540(5) . ?
C9 H9 0.9800 . ?
C10 C11 1.500(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.373(4) . ?
C12 C13 1.394(4) . ?
C13 C14 1.361(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.395(5) . ?
C14 H14 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C4 N1 C5 115.1(3) . . ?
C4 N1 H1A 106(2) . . ?
C5 N1 H1A 109(2) . . ?
C4 N1 H2 111(3) . . ?
C5 N1 H2 114(3) . . ?
H1A N1 H2 101(4) . . ?
C15 N2 C11 117.9(3) . . ?
C1 O1 H1 131(5) . . ?
C15 O2 C16 117.6(3) . . ?
O1 C1 C2 109.7(3) . . ?
O1 C1 C9 107.6(3) . . ?
C2 C1 C9 114.2(3) . . ?
O1 C1 C5 107.7(2) . . ?
C2 C1 C5 111.1(3) . . ?
C9 C1 C5 106.3(3) . . ?
C1 C2 C3 112.5(3) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C2 110.8(3) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
N1 C4 C3 109.4(3) . . ?
N1 C4 H4A 109.8 . . ?
C3 C4 H4A 109.8 . . ?
N1 C4 H4B 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
N1 C5 C12 109.8(2) . . ?
N1 C5 C6 107.1(3) . . ?
C12 C5 C6 110.5(2) . . ?
N1 C5 C1 107.3(2) . . ?
C12 C5 C1 110.3(2) . . ?
C6 C5 C1 111.7(3) . . ?
C5 C6 C7 113.8(3) . . ?
C5 C6 H6A 108.8 . . ?
C7 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
C7 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C17 C7 C6 114.6(3) . . ?
C17 C7 C8 114.5(4) . . ?
C6 C7 C8 110.1(3) . . ?
C17 C7 H7 105.6 . . ?
C6 C7 H7 105.6 . . ?
C8 C7 H7 105.6 . . ?
C9 C8 C7 118.4(3) . . ?
C9 C8 H8A 107.7 . . ?
C7 C8 H8A 107.7 . . ?
C9 C8 H8B 107.7 . . ?
C7 C8 H8B 107.7 . . ?
H8A C8 H8B 107.1 . . ?
C1 C9 C8 110.5(3) . . ?
C1 C9 C10 109.2(3) . . ?
C8 C9 C10 114.1(3) . . ?
C1 C9 H9 107.6 . . ?
C8 C9 H9 107.6 . . ?
C10 C9 H9 107.6 . . ?
C11 C10 C9 114.1(3) . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
N2 C11 C12 122.8(3) . . ?
N2 C11 C10 114.5(3) . . ?
C12 C11 C10 122.7(3) . . ?
C11 C12 C13 117.7(3) . . ?
C11 C12 C5 120.4(3) . . ?
C13 C12 C5 121.6(3) . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 117.5(3) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 H14 121.3 . . ?
N2 C15 O2 119.9(3) . . ?
N2 C15 C14 123.9(3) . . ?
O2 C15 C14 116.2(3) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 C17 H17A 109.5 . . ?
C7 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C7 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O1 C1 C2 C3 -63.1(3) . . . . ?
C9 C1 C2 C3 176.0(3) . . . . ?
C5 C1 C2 C3 55.8(4) . . . . ?
C1 C2 C3 C4 -55.4(4) . . . . ?
C5 N1 C4 C3 -58.5(3) . . . . ?
C2 C3 C4 N1 54.4(4) . . . . ?
C4 N1 C5 C12 -62.2(3) . . . . ?
C4 N1 C5 C6 177.7(3) . . . . ?
C4 N1 C5 C1 57.7(3) . . . . ?
O1 C1 C5 N1 65.8(3) . . . . ?
C2 C1 C5 N1 -54.4(3) . . . . ?
C9 C1 C5 N1 -179.1(3) . . . . ?
O1 C1 C5 C12 -174.6(3) . . . . ?
C2 C1 C5 C12 65.2(3) . . . . ?
C9 C1 C5 C12 -59.5(4) . . . . ?
O1 C1 C5 C6 -51.3(4) . . . . ?
C2 C1 C5 C6 -171.5(3) . . . . ?
C9 C1 C5 C6 63.8(3) . . . . ?
N1 C5 C6 C7 -174.5(3) . . . . ?
C12 C5 C6 C7 65.9(4) . . . . ?
C1 C5 C6 C7 -57.3(4) . . . . ?
C5 C6 C7 C17 -87.7(4) . . . . ?
C5 C6 C7 C8 43.0(4) . . . . ?
C17 C7 C8 C9 89.4(5) . . . . ?
C6 C7 C8 C9 -41.3(5) . . . . ?
O1 C1 C9 C8 56.2(4) . . . . ?
C2 C1 C9 C8 178.2(3) . . . . ?
C5 C1 C9 C8 -59.0(4) . . . . ?
O1 C1 C9 C10 -177.5(3) . . . . ?
C2 C1 C9 C10 -55.6(4) . . . . ?
C5 C1 C9 C10 67.3(4) . . . . ?
C7 C8 C9 C1 51.5(5) . . . . ?
C7 C8 C9 C10 -72.0(5) . . . . ?
C1 C9 C10 C11 -41.5(5) . . . . ?
C8 C9 C10 C11 82.7(4) . . . . ?
C15 N2 C11 C12 -0.5(5) . . . . ?
C15 N2 C11 C10 177.0(3) . . . . ?
C9 C10 C11 N2 -170.1(3) . . . . ?
C9 C10 C11 C12 7.5(5) . . . . ?
N2 C11 C12 C13 3.7(5) . . . . ?
C10 C11 C12 C13 -173.7(3) . . . . ?
N2 C11 C12 C5 177.1(3) . . . . ?
C10 C11 C12 C5 -0.3(5) . . . . ?
N1 C5 C12 C11 144.9(3) . . . . ?
C6 C5 C12 C11 -97.2(3) . . . . ?
C1 C5 C12 C11 26.8(4) . . . . ?
N1 C5 C12 C13 -42.0(4) . . . . ?
C6 C5 C12 C13 76.0(4) . . . . ?
C1 C5 C12 C13 -160.0(3) . . . . ?
C11 C12 C13 C14 -3.0(5) . . . . ?
C5 C12 C13 C14 -176.3(3) . . . . ?
C12 C13 C14 C15 -0.5(5) . . . . ?
C11 N2 C15 O2 177.9(3) . . . . ?
C11 N2 C15 C14 -3.5(5) . . . . ?
C16 O2 C15 N2 1.4(5) . . . . ?
C16 O2 C15 C14 -177.3(4) . . . . ?
C13 C14 C15 N2 4.0(5) . . . . ?
C13 C14 C15 O2 -177.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 Cl1 0.80(2) 2.59(3) 3.339(3) 158(6) .
N1 H1A Cl1 0.857(18) 2.31(2) 3.139(3) 163(3) .
N1 H2 Cl1 0.842(19) 2.31(2) 3.138(3) 169(4) 3_755

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.045
