# 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_st180
_database_code_depnum_ccdc_archive 'CCDC 1819144'
_audit_update_record             
;
2018-01-24 deposited with the CCDC.
2018-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H21 Cl N2 O'
_chemical_formula_weight         232.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.1121(7)
_cell_length_b                   10.4420(6)
_cell_length_c                   12.0205(14)
_cell_angle_alpha                95.695(8)
_cell_angle_beta                 91.086(8)
_cell_angle_gamma                97.671(5)
_cell_volume                     1251.02(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.0(1)
_cell_measurement_reflns_used    2814
_cell_measurement_theta_min      3.8770
_cell_measurement_theta_max      28.9130

_exptl_crystal_description       Parallelepiped
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.284
_shelx_estimated_absorpt_T_min   0.871
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.64862
_exptl_absorpt_correction_T_max  1.00000
_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) 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'enhance (mo) x-ray source'
_diffrn_measurement_device_type  'xcalibur, sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1048
_diffrn_reflns_number            7456
_diffrn_reflns_av_unetI/netI     0.0882
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.602
_diffrn_reflns_theta_max         28.887
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.681
_diffrn_measured_fraction_theta_full 0.810
_diffrn_reflns_Laue_measured_fraction_max 0.681
_diffrn_reflns_Laue_measured_fraction_full 0.810
_diffrn_reflns_point_group_measured_fraction_max 0.681
_diffrn_reflns_point_group_measured_fraction_full 0.810
_reflns_number_total             4487
_reflns_number_gt                2904
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       
; 
crysalispro, agilent technologies, 
version 1.171.37.35 (release 13-08-2014 crysalis171 .net) 
(compiled aug 13 2014,18:06:01) 
;
_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_reduction        
; 
crysalispro, agilent technologies, 
version 1.171.37.35 (release 13-08-2014 crysalis171 .net) 
(compiled aug 13 2014,18:06:01) 
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
'ORTEX - P. McArdle, J.Appl.Cryst.,1995,28,65-65.'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1410P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4487
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1018
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.2128
_refine_ls_wR_factor_gt          0.1965
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.26313(9) 0.54409(9) 0.82892(8) 0.0199(3) Uani 1 1 d . . . . .
Cl2 Cl 0.25116(11) 0.99471(9) 0.45630(9) 0.0288(3) Uani 1 1 d . . . . .
O3 O -0.0296(3) 0.3660(2) 0.4013(2) 0.0203(6) Uani 1 1 d . . . . .
O4 O 0.5231(3) 0.6033(2) 0.4001(2) 0.0195(6) Uani 1 1 d . . . . .
N4 N 0.3887(3) 0.7412(3) 0.4813(2) 0.0138(6) Uani 1 1 d . . . . .
H4 H 0.359221 0.814470 0.479594 0.018 Uiso 1 1 calc R U . . .
N1 N 0.0804(3) 0.3276(3) 0.6815(3) 0.0146(6) Uani 1 1 d . . . . .
H1 H 0.114637 0.399220 0.737963 0.019 Uiso 1 1 calc R U . . .
N3 N 0.4348(3) 0.7206(3) 0.6788(2) 0.0127(6) Uani 1 1 d . . . . .
H3 H 0.401419 0.667081 0.737460 0.016 Uiso 1 1 calc R U . . .
N2 N 0.1125(3) 0.2535(3) 0.4856(3) 0.0163(7) Uani 1 1 d . . . . .
H2 H 0.143426 0.180760 0.486084 0.021 Uiso 1 1 calc R U . . .
C1 C -0.0687(3) 0.3287(4) 0.6694(3) 0.0165(8) Uani 1 1 d . . . . .
H1A H -0.088794 0.357087 0.597238 0.021 Uiso 1 1 calc R U . . .
H1B H -0.113778 0.240915 0.670739 0.021 Uiso 1 1 calc R U . . .
C2 C -0.1224(4) 0.4157(4) 0.7594(3) 0.0211(8) Uani 1 1 d . . . . .
H2A H -0.218879 0.403839 0.749815 0.027 Uiso 1 1 calc R U . . .
H2B H -0.090773 0.504850 0.747018 0.027 Uiso 1 1 calc R U . . .
C3 C -0.0892(5) 0.3993(4) 0.8801(3) 0.0276(10) Uani 1 1 d . . . . .
H3A H 0.006719 0.420189 0.892071 0.036 Uiso 1 1 calc R U . . .
H3B H -0.129989 0.462922 0.927309 0.036 Uiso 1 1 calc R U . . .
C4 C -0.1313(5) 0.2674(4) 0.9199(4) 0.0324(10) Uani 1 1 d . . . . .
H4A H -0.226792 0.245384 0.906047 0.042 Uiso 1 1 calc R U . . .
H4B H -0.115147 0.274912 1.000203 0.042 Uiso 1 1 calc R U . . .
C5 C -0.0625(5) 0.1524(4) 0.8670(4) 0.0338(11) Uani 1 1 d . . . . .
H5A H -0.071369 0.084632 0.917020 0.044 Uiso 1 1 calc R U . . .
H5B H -0.110255 0.117314 0.797530 0.044 Uiso 1 1 calc R U . . .
C6 C 0.0862(5) 0.1856(4) 0.8423(4) 0.0302(10) Uani 1 1 d . . . . .
H6A H 0.121709 0.264143 0.889179 0.039 Uiso 1 1 calc R U . . .
H6B H 0.132715 0.116199 0.864320 0.039 Uiso 1 1 calc R U . . .
C7 C 0.1182(4) 0.2055(4) 0.7219(3) 0.0211(8) Uani 1 1 d . . . . .
H7A H 0.213378 0.205634 0.713271 0.027 Uiso 1 1 calc R U . . .
H7B H 0.072838 0.131919 0.673945 0.027 Uiso 1 1 calc R U . . .
C8 C 0.1505(4) 0.3535(4) 0.5746(3) 0.0170(8) Uani 1 1 d . . . . .
H8A H 0.130211 0.435499 0.551922 0.022 Uiso 1 1 calc R U . . .
H8B H 0.246174 0.361429 0.588549 0.022 Uiso 1 1 calc R U . . .
C9 C 0.0293(4) 0.2703(3) 0.4008(3) 0.0146(7) Uani 1 1 d . . . . .
C10 C 0.0170(4) 0.1678(4) 0.3055(3) 0.0216(9) Uani 1 1 d . . . . .
H10 H 0.054842 0.092214 0.311131 0.028 Uiso 1 1 calc R U . . .
C11 C -0.0467(5) 0.1834(4) 0.2138(4) 0.0298(10) Uani 1 1 d . . . . .
H11A H -0.084570 0.259021 0.208116 0.039 Uiso 1 1 calc R U . . .
H11B H -0.054397 0.118933 0.153931 0.039 Uiso 1 1 calc R U . . .
C12 C 0.4041(4) 0.8564(4) 0.7128(3) 0.0195(8) Uani 1 1 d . . . . .
H12A H 0.308704 0.856750 0.703291 0.025 Uiso 1 1 calc R U . . .
H12B H 0.447962 0.914047 0.662117 0.025 Uiso 1 1 calc R U . . .
C13 C 0.4461(4) 0.9112(4) 0.8317(3) 0.0237(9) Uani 1 1 d . . . . .
H13A H 0.411807 0.847861 0.881429 0.031 Uiso 1 1 calc R U . . .
H13B H 0.403400 0.988178 0.849725 0.031 Uiso 1 1 calc R U . . .
C14 C 0.5951(4) 0.9472(4) 0.8565(4) 0.0268(9) Uani 1 1 d . . . . .
H14A H 0.609344 1.030245 0.901952 0.035 Uiso 1 1 calc R U . . .
H14B H 0.638775 0.958829 0.786379 0.035 Uiso 1 1 calc R U . . .
C15 C 0.6639(4) 0.8493(4) 0.9168(3) 0.0257(9) Uani 1 1 d . . . . .
H15A H 0.758465 0.863504 0.902279 0.033 Uiso 1 1 calc R U . . .
H15B H 0.654520 0.868461 0.996628 0.033 Uiso 1 1 calc R U . . .
C16 C 0.6133(4) 0.7059(4) 0.8854(3) 0.0254(9) Uani 1 1 d . . . . .
H16A H 0.653616 0.656201 0.937636 0.033 Uiso 1 1 calc R U . . .
H16B H 0.517677 0.692620 0.895468 0.033 Uiso 1 1 calc R U . . .
C17 C 0.6399(4) 0.6507(4) 0.7676(3) 0.0220(9) Uani 1 1 d . . . . .
H17A H 0.605523 0.558829 0.759784 0.029 Uiso 1 1 calc R U . . .
H17B H 0.735817 0.657664 0.759988 0.029 Uiso 1 1 calc R U . . .
C18 C 0.5823(4) 0.7112(4) 0.6704(3) 0.0164(8) Uani 1 1 d . . . . .
H18A H 0.630225 0.797567 0.667355 0.021 Uiso 1 1 calc R U . . .
H18B H 0.596761 0.659643 0.601152 0.021 Uiso 1 1 calc R U . . .
C19 C 0.3571(4) 0.6661(3) 0.5728(3) 0.0151(7) Uani 1 1 d . . . . .
H19A H 0.375420 0.578097 0.552617 0.020 Uiso 1 1 calc R U . . .
H19B H 0.262436 0.662302 0.586183 0.020 Uiso 1 1 calc R U . . .
C20 C 0.4645(4) 0.6986(3) 0.3973(3) 0.0150(8) Uani 1 1 d . . . . .
C21 C 0.4657(4) 0.7731(4) 0.2979(3) 0.0206(8) Uani 1 1 d . . . . .
H21 H 0.430639 0.851255 0.302123 0.027 Uiso 1 1 calc R U . . .
C22 C 0.5160(4) 0.7290(4) 0.2045(3) 0.0257(9) Uani 1 1 d . . . . .
H22A H 0.551128 0.650874 0.200092 0.033 Uiso 1 1 calc R U . . .
H22B H 0.516532 0.775866 0.142624 0.033 Uiso 1 1 calc R U . . .


_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
O3 C9 1.229(4) . ?
O4 C20 1.227(4) . ?
N4 C20 1.355(5) . ?
N4 C19 1.429(4) . ?
N4 H4 0.8600 . ?
N1 C7 1.501(5) . ?
N1 C8 1.510(5) . ?
N1 C1 1.513(4) . ?
N1 H1 0.9800 . ?
N3 C19 1.505(5) . ?
N3 C12 1.510(4) . ?
N3 C18 1.513(4) . ?
N3 H3 0.9800 . ?
N2 C9 1.349(5) . ?
N2 C8 1.427(5) . ?
N2 H2 0.8600 . ?
C1 C2 1.500(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.514(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.512(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.555(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.539(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.518(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.479(5) . ?
C10 C11 1.301(6) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9300 . ?
C11 H11B 0.9300 . ?
C12 C13 1.516(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.520(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.540(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.523(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.518(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.523(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.489(5) . ?
C21 C22 1.307(6) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9300 . ?
C22 H22B 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
C20 N4 C19 121.0(3) . . ?
C20 N4 H4 119.5 . . ?
C19 N4 H4 119.5 . . ?
C7 N1 C8 109.7(3) . . ?
C7 N1 C1 114.0(3) . . ?
C8 N1 C1 111.9(3) . . ?
C7 N1 H1 107.0 . . ?
C8 N1 H1 107.0 . . ?
C1 N1 H1 107.0 . . ?
C19 N3 C12 109.5(3) . . ?
C19 N3 C18 112.4(3) . . ?
C12 N3 C18 113.9(3) . . ?
C19 N3 H3 106.9 . . ?
C12 N3 H3 106.9 . . ?
C18 N3 H3 106.9 . . ?
C9 N2 C8 121.7(3) . . ?
C9 N2 H2 119.2 . . ?
C8 N2 H2 119.2 . . ?
C2 C1 N1 113.2(3) . . ?
C2 C1 H1A 108.9 . . ?
N1 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
N1 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C1 C2 C3 118.2(3) . . ?
C1 C2 H2A 107.8 . . ?
C3 C2 H2A 107.8 . . ?
C1 C2 H2B 107.8 . . ?
C3 C2 H2B 107.7 . . ?
H2A C2 H2B 107.1 . . ?
C4 C3 C2 117.4(4) . . ?
C4 C3 H3A 108.0 . . ?
C2 C3 H3A 108.0 . . ?
C4 C3 H3B 108.0 . . ?
C2 C3 H3B 108.0 . . ?
H3A C3 H3B 107.2 . . ?
C3 C4 C5 117.1(4) . . ?
C3 C4 H4A 108.0 . . ?
C5 C4 H4A 108.0 . . ?
C3 C4 H4B 108.0 . . ?
C5 C4 H4B 108.0 . . ?
H4A C4 H4B 107.3 . . ?
C6 C5 C4 115.6(4) . . ?
C6 C5 H5A 108.4 . . ?
C4 C5 H5A 108.4 . . ?
C6 C5 H5B 108.4 . . ?
C4 C5 H5B 108.4 . . ?
H5A C5 H5B 107.4 . . ?
C7 C6 C5 116.2(4) . . ?
C7 C6 H6A 108.2 . . ?
C5 C6 H6A 108.2 . . ?
C7 C6 H6B 108.2 . . ?
C5 C6 H6B 108.2 . . ?
H6A C6 H6B 107.4 . . ?
N1 C7 C6 115.6(3) . . ?
N1 C7 H7A 108.4 . . ?
C6 C7 H7A 108.4 . . ?
N1 C7 H7B 108.4 . . ?
C6 C7 H7B 108.4 . . ?
H7A C7 H7B 107.4 . . ?
N2 C8 N1 112.8(3) . . ?
N2 C8 H8A 109.0 . . ?
N1 C8 H8A 109.0 . . ?
N2 C8 H8B 109.0 . . ?
N1 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
O3 C9 N2 122.3(3) . . ?
O3 C9 C10 122.2(3) . . ?
N2 C9 C10 115.5(3) . . ?
C11 C10 C9 120.1(4) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
N3 C12 C13 115.5(3) . . ?
N3 C12 H12A 108.4 . . ?
C13 C12 H12A 108.4 . . ?
N3 C12 H12B 108.4 . . ?
C13 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
C12 C13 C14 116.6(3) . . ?
C12 C13 H13A 108.1 . . ?
C14 C13 H13A 108.1 . . ?
C12 C13 H13B 108.1 . . ?
C14 C13 H13B 108.1 . . ?
H13A C13 H13B 107.3 . . ?
C13 C14 C15 116.1(3) . . ?
C13 C14 H14A 108.3 . . ?
C15 C14 H14A 108.3 . . ?
C13 C14 H14B 108.3 . . ?
C15 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C16 C15 C14 116.7(3) . . ?
C16 C15 H15A 108.1 . . ?
C14 C15 H15A 108.1 . . ?
C16 C15 H15B 108.1 . . ?
C14 C15 H15B 108.1 . . ?
H15A C15 H15B 107.3 . . ?
C17 C16 C15 116.5(4) . . ?
C17 C16 H16A 108.2 . . ?
C15 C16 H16A 108.2 . . ?
C17 C16 H16B 108.2 . . ?
C15 C16 H16B 108.2 . . ?
H16A C16 H16B 107.3 . . ?
C16 C17 C18 117.8(3) . . ?
C16 C17 H17A 107.9 . . ?
C18 C17 H17A 107.9 . . ?
C16 C17 H17B 107.9 . . ?
C18 C17 H17B 107.9 . . ?
H17A C17 H17B 107.2 . . ?
N3 C18 C17 113.5(3) . . ?
N3 C18 H18A 108.9 . . ?
C17 C18 H18A 108.9 . . ?
N3 C18 H18B 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
N4 C19 N3 113.0(3) . . ?
N4 C19 H19A 109.0 . . ?
N3 C19 H19A 109.0 . . ?
N4 C19 H19B 109.0 . . ?
N3 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
O4 C20 N4 123.3(3) . . ?
O4 C20 C21 122.2(3) . . ?
N4 C20 C21 114.5(3) . . ?
C22 C21 C20 120.3(4) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 H22A 120.0 . . ?
C21 C22 H22B 120.0 . . ?
H22A C22 H22B 120.0 . . ?

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
C7 N1 C1 C2 106.2(4) . . . . ?
C8 N1 C1 C2 -128.6(3) . . . . ?
N1 C1 C2 C3 -51.9(5) . . . . ?
C1 C2 C3 C4 -58.6(5) . . . . ?
C2 C3 C4 C5 65.9(6) . . . . ?
C3 C4 C5 C6 36.9(6) . . . . ?
C4 C5 C6 C7 -100.3(5) . . . . ?
C8 N1 C7 C6 164.4(3) . . . . ?
C1 N1 C7 C6 -69.2(4) . . . . ?
C5 C6 C7 N1 71.2(5) . . . . ?
C9 N2 C8 N1 104.6(4) . . . . ?
C7 N1 C8 N2 62.5(4) . . . . ?
C1 N1 C8 N2 -65.0(4) . . . . ?
C8 N2 C9 O3 -8.1(6) . . . . ?
C8 N2 C9 C10 170.1(3) . . . . ?
O3 C9 C10 C11 7.1(6) . . . . ?
N2 C9 C10 C11 -171.1(4) . . . . ?
C19 N3 C12 C13 165.1(3) . . . . ?
C18 N3 C12 C13 -68.2(4) . . . . ?
N3 C12 C13 C14 71.4(5) . . . . ?
C12 C13 C14 C15 -101.4(4) . . . . ?
C13 C14 C15 C16 36.0(5) . . . . ?
C14 C15 C16 C17 67.6(5) . . . . ?
C15 C16 C17 C18 -59.6(5) . . . . ?
C19 N3 C18 C17 -129.7(3) . . . . ?
C12 N3 C18 C17 105.0(4) . . . . ?
C16 C17 C18 N3 -51.2(4) . . . . ?
C20 N4 C19 N3 105.5(4) . . . . ?
C12 N3 C19 N4 60.2(4) . . . . ?
C18 N3 C19 N4 -67.4(4) . . . . ?
C19 N4 C20 O4 -8.9(5) . . . . ?
C19 N4 C20 C21 168.2(3) . . . . ?
O4 C20 C21 C22 8.6(6) . . . . ?
N4 C20 C21 C22 -168.4(4) . . . . ?

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
N4 H4 Cl2 0.86 2.34 3.188(3) 170.7 .
N1 H1 Cl1 0.98 2.18 3.103(3) 156.9 .
N3 H3 Cl1 0.98 2.16 3.097(3) 159.1 .
N2 H2 Cl2 0.86 2.35 3.199(3) 168.6 1_545
C1 H1A O3 0.97 2.45 3.309(4) 147.6 .
C1 H1B Cl2 0.97 2.93 3.783(4) 147.5 2_566
C2 H2B O3 0.97 2.57 3.368(5) 139.7 2_566
C8 H8A O3 0.97 2.45 3.311(4) 147.7 2_566
C8 H8B O4 0.97 2.31 3.276(5) 171.9 2_666
C10 H10 Cl2 0.93 2.96 3.714(4) 138.7 1_545
C17 H17A O4 0.97 2.63 3.385(5) 134.8 2_666
C18 H18A Cl2 0.97 2.89 3.773(4) 151.4 2_676
C18 H18B O4 0.97 2.51 3.348(5) 145.2 .
C19 H19A O4 0.97 2.38 3.251(4) 148.8 2_666
C19 H19B O3 0.97 2.34 3.307(5) 172.8 2_566

_refine_diff_density_max         0.852
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.099

####################################################################### 
# 
# 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_azosm
_database_code_depnum_ccdc_archive 'CCDC 1819145'
_audit_update_record             
;
2018-01-24 deposited with the CCDC.
2018-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 Cl N O'
_chemical_formula_weight         179.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   11.3190(18)
_cell_length_b                   10.9194(16)
_cell_length_c                   7.7658(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.269(13)
_cell_angle_gamma                90
_cell_volume                     959.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.0(1)
_cell_measurement_reflns_used    2163
_cell_measurement_theta_min      4.1450
_cell_measurement_theta_max      28.0840

_exptl_crystal_description       Parallelepiped
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.347
_shelx_estimated_absorpt_T_min   0.846
_shelx_estimated_absorpt_T_max   0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92227
_exptl_absorpt_correction_T_max  1.00000
_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) 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'enhance (mo) x-ray source'
_diffrn_measurement_device_type  'xcalibur, sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1048
_diffrn_reflns_number            7528
_diffrn_reflns_av_unetI/netI     0.0725
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.600
_diffrn_reflns_theta_max         29.273
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2345
_reflns_number_gt                1949
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       
; 
crysalispro, agilent technologies, 
version 1.171.37.35 (release 13-08-2014 crysalis171 .net) 
(compiled aug 13 2014,18:06:01) 
;
_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_reduction        
; 
crysalispro, agilent technologies, 
version 1.171.37.35 (release 13-08-2014 crysalis171 .net) 
(compiled aug 13 2014,18:06:01) 
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'ORTEX - P. McArdle, J.Appl.Cryst.,1995,28,65-65.'
_computing_publication_material  
'Oscail - P. McArdle, J.Appl.Cryst.,2017,50,320-326.'
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²+2.5766P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2345
_refine_ls_number_parameters     147
_refine_ls_number_restraints     102
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0857
_refine_ls_wR_factor_ref         0.2182
_refine_ls_wR_factor_gt          0.2083
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.81004(11) 0.98048(10) 0.83094(15) 0.0335(3) Uani 1 1 d . . . . .
O1 O 0.8932(4) 0.7716(3) 0.6155(4) 0.0475(10) Uani 1 1 d . . . . .
H1O1 H 0.873106 0.826814 0.680598 0.062 Uiso 1 1 calc R U . . .
N1 N 0.8218(3) 0.5815(3) 0.7268(5) 0.0297(8) Uani 1 1 d . . . . .
H1 H 0.798782 0.556532 0.610174 0.039 Uiso 1 1 calc R U . . .
C1 C 0.8646(4) 0.4692(5) 0.8200(8) 0.0431(12) Uani 1 1 d . . . . .
H1A H 0.904101 0.497765 0.923571 0.056 Uiso 1 1 calc R U . A 1
H1B H 0.925130 0.432933 0.748190 0.056 Uiso 1 1 calc R U . A 1
C2 C 0.7826(13) 0.3636(14) 0.876(2) 0.046(3) Uani 0.4 1 d . . P B 1
H2A H 0.823695 0.289556 0.841561 0.060 Uiso 0.4 1 calc R U P B 1
H2B H 0.785053 0.364692 1.000562 0.060 Uiso 0.4 1 calc R U P B 1
C2A C 0.8061(10) 0.3587(8) 0.7688(14) 0.047(2) Uani 0.6 1 d . . P B 2
H2A1 H 0.830352 0.351614 0.649607 0.061 Uiso 0.6 1 calc R U P B 2
H2A2 H 0.852323 0.297379 0.829278 0.061 Uiso 0.6 1 calc R U P B 2
C3 C 0.6710(16) 0.3433(14) 0.836(3) 0.055(4) Uani 0.4 1 d . . P B 1
H3A H 0.624636 0.380762 0.926903 0.071 Uiso 0.4 1 calc R U P B 1
H3B H 0.659002 0.255597 0.846157 0.071 Uiso 0.4 1 calc R U P B 1
C3A C 0.6999(11) 0.3059(12) 0.7641(15) 0.055(3) Uani 0.6 1 d . . P B 2
H3A1 H 0.690769 0.260890 0.870912 0.071 Uiso 0.6 1 calc R U P B 2
H3A2 H 0.701158 0.245945 0.672037 0.071 Uiso 0.6 1 calc R U P B 2
C4 C 0.6119(8) 0.3832(9) 0.6606(12) 0.048(2) Uani 0.7 1 d . . P B 1
H4A H 0.666763 0.417468 0.578047 0.062 Uiso 0.7 1 calc R U P B 1
H4B H 0.562718 0.320569 0.608211 0.062 Uiso 0.7 1 calc R U P B 1
C4A C 0.568(3) 0.398(3) 0.735(5) 0.074(9) Uani 0.3 1 d . . P B 2
H4A1 H 0.544857 0.380968 0.616785 0.097 Uiso 0.3 1 calc R U P B 2
H4A2 H 0.509707 0.356080 0.805005 0.097 Uiso 0.3 1 calc R U P B 2
C5 C 0.5509(14) 0.4682(19) 0.751(3) 0.056(4) Uani 0.5 1 d . . P B 1
H5A H 0.504713 0.424144 0.835784 0.073 Uiso 0.5 1 calc R U P B 1
H5B H 0.495008 0.505345 0.671674 0.073 Uiso 0.5 1 calc R U P B 1
C5A C 0.5386(15) 0.5200(17) 0.755(2) 0.052(3) Uani 0.5 1 d . . P B 2
H5A1 H 0.465755 0.531270 0.690559 0.067 Uiso 0.5 1 calc R U P B 2
H5A2 H 0.518003 0.529191 0.875402 0.067 Uiso 0.5 1 calc R U P B 2
C6 C 0.6197(15) 0.5851(15) 0.857(3) 0.065(4) Uani 0.4 1 d . . P B 1
H6A H 0.560447 0.648565 0.870812 0.084 Uiso 0.4 1 calc R U P B 1
H6B H 0.636375 0.554461 0.972092 0.084 Uiso 0.4 1 calc R U P B 1
C6A C 0.6021(8) 0.6120(11) 0.7193(19) 0.063(3) Uani 0.6 1 d . . P B 2
H6A1 H 0.551931 0.683300 0.733165 0.082 Uiso 0.6 1 calc R U P B 2
H6A2 H 0.619368 0.606188 0.597300 0.082 Uiso 0.6 1 calc R U P B 2
C7 C 0.7172(4) 0.6422(6) 0.8072(9) 0.0534(16) Uani 1 1 d . . . . .
H7A H 0.747080 0.684933 0.907948 0.069 Uiso 1 1 calc R U . B 1
H7B H 0.691879 0.704993 0.726757 0.069 Uiso 1 1 calc R U . B 1
C8 C 0.9239(4) 0.6696(5) 0.7108(6) 0.0365(10) Uani 1 1 d . . . . .
H8A H 0.949275 0.695009 0.824749 0.047 Uiso 1 1 calc R U . . .
H8B H 0.989703 0.628399 0.655967 0.047 Uiso 1 1 calc R U . . .


_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
O1 C8 1.380(6) . ?
O1 H1O1 0.8200 . ?
N1 C7 1.496(6) . ?
N1 C1 1.503(6) . ?
N1 C8 1.509(6) . ?
N1 H1 0.9800 . ?
C1 C2A 1.432(12) . ?
C1 C2 1.543(15) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.32(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2A C3A 1.332(16) . ?
C2A H2A1 0.9700 . ?
C2A H2A2 0.9700 . ?
C3 C4 1.58(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3A C4A 1.82(3) . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
C4 C5 1.35(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4A C5A 1.38(3) . ?
C4A H4A1 0.9700 . ?
C4A H4A2 0.9700 . ?
C5 C6 1.71(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5A C6A 1.27(2) . ?
C5A H5A1 0.9700 . ?
C5A H5A2 0.9700 . ?
C6 C7 1.328(17) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6A C7 1.505(10) . ?
C6A H6A1 0.9700 . ?
C6A H6A2 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?

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 O1 H1O1 109.5 . . ?
C7 N1 C1 114.5(4) . . ?
C7 N1 C8 111.1(4) . . ?
C1 N1 C8 108.3(4) . . ?
C7 N1 H1 107.6 . . ?
C1 N1 H1 107.6 . . ?
C8 N1 H1 107.6 . . ?
C2A C1 N1 114.0(6) . . ?
N1 C1 C2 123.5(7) . . ?
N1 C1 H1A 106.5 . . ?
C2 C1 H1A 106.5 . . ?
N1 C1 H1B 106.5 . . ?
C2 C1 H1B 106.5 . . ?
H1A C1 H1B 106.5 . . ?
C3 C2 C1 129.6(14) . . ?
C3 C2 H2A 104.9 . . ?
C1 C2 H2A 104.9 . . ?
C3 C2 H2B 104.9 . . ?
C1 C2 H2B 104.9 . . ?
H2A C2 H2B 105.8 . . ?
C3A C2A C1 142.0(10) . . ?
C3A C2A H2A1 101.5 . . ?
C1 C2A H2A1 101.5 . . ?
C3A C2A H2A2 101.5 . . ?
C1 C2A H2A2 101.5 . . ?
H2A1 C2A H2A2 104.6 . . ?
C2 C3 C4 123.8(16) . . ?
C2 C3 H3A 106.4 . . ?
C4 C3 H3A 106.4 . . ?
C2 C3 H3B 106.4 . . ?
C4 C3 H3B 106.4 . . ?
H3A C3 H3B 106.5 . . ?
C2A C3A C4A 120.4(14) . . ?
C2A C3A H3A1 107.2 . . ?
C4A C3A H3A1 107.2 . . ?
C2A C3A H3A2 107.2 . . ?
C4A C3A H3A2 107.2 . . ?
H3A1 C3A H3A2 106.9 . . ?
C5 C4 C3 87.5(12) . . ?
C5 C4 H4A 114.1 . . ?
C3 C4 H4A 114.1 . . ?
C5 C4 H4B 114.1 . . ?
C3 C4 H4B 114.1 . . ?
H4A C4 H4B 111.3 . . ?
C5A C4A C3A 136(2) . . ?
C5A C4A H4A1 103.2 . . ?
C3A C4A H4A1 103.2 . . ?
C5A C4A H4A2 103.2 . . ?
C3A C4A H4A2 103.2 . . ?
H4A1 C4A H4A2 105.2 . . ?
C4 C5 C6 122.1(13) . . ?
C4 C5 H5A 106.8 . . ?
C6 C5 H5A 106.8 . . ?
C4 C5 H5B 106.8 . . ?
C6 C5 H5B 106.8 . . ?
H5A C5 H5B 106.7 . . ?
C6A C5A C4A 127(2) . . ?
C6A C5A H5A1 105.5 . . ?
C4A C5A H5A1 105.5 . . ?
C6A C5A H5A2 105.5 . . ?
C4A C5A H5A2 105.5 . . ?
H5A1 C5A H5A2 106.1 . . ?
C7 C6 C5 126.0(16) . . ?
C7 C6 H6A 105.8 . . ?
C5 C6 H6A 105.8 . . ?
C7 C6 H6B 105.8 . . ?
C5 C6 H6B 105.8 . . ?
H6A C6 H6B 106.2 . . ?
C5A C6A C7 124.4(13) . . ?
C5A C6A H6A1 106.2 . . ?
C7 C6A H6A1 106.2 . . ?
C5A C6A H6A2 106.2 . . ?
C7 C6A H6A2 106.2 . . ?
H6A1 C6A H6A2 106.4 . . ?
C6 C7 N1 125.1(9) . . ?
N1 C7 C6A 113.5(6) . . ?
C6 C7 H7A 106.0 . . ?
N1 C7 H7A 106.0 . . ?
C6 C7 H7B 106.0 . . ?
N1 C7 H7B 106.0 . . ?
H7A C7 H7B 106.3 . . ?
O1 C8 N1 111.6(4) . . ?
O1 C8 H8A 109.3 . . ?
N1 C8 H8A 109.3 . . ?
O1 C8 H8B 109.3 . . ?
N1 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?

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
C7 N1 C1 C2A 86.9(7) . . . . ?
C8 N1 C1 C2A -148.5(6) . . . . ?
C7 N1 C1 C2 49.5(10) . . . . ?
C8 N1 C1 C2 174.1(9) . . . . ?
N1 C1 C2 C3 10(2) . . . . ?
N1 C1 C2A C3A -61.5(17) . . . . ?
C1 C2 C3 C4 31(3) . . . . ?
C1 C2A C3A C4A 32(2) . . . . ?
C2 C3 C4 C5 -109.7(19) . . . . ?
C2A C3A C4A C5A -19(5) . . . . ?
C3 C4 C5 C6 63.4(19) . . . . ?
C3A C4A C5A C6A 39(6) . . . . ?
C4 C5 C6 C7 34(3) . . . . ?
C4A C5A C6A C7 -64(3) . . . . ?
C5 C6 C7 N1 -39(2) . . . . ?
C1 N1 C7 C6 -48.2(15) . . . . ?
C8 N1 C7 C6 -171.3(14) . . . . ?
C1 N1 C7 C6A -100.4(8) . . . . ?
C8 N1 C7 C6A 136.5(8) . . . . ?
C5A C6A C7 N1 87.4(15) . . . . ?
C7 N1 C8 O1 -57.7(5) . . . . ?
C1 N1 C8 O1 175.7(4) . . . . ?

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
_geom_hbond_publ_flag
O1 H1O1 Cl1 0.82 2.17 2.984(4) 174.2 . yes
N1 H1 Cl1 0.98 2.21 3.150(4) 160.3 2_564 yes
C7 H7A^a O1 0.97 2.35 3.247(7) 152.9 2_565 yes
C8 H8A O1 0.97 2.38 3.229(6) 146.3 2_565 yes
C8 H8B Cl1 0.97 2.78 3.667(5) 151.6 4_757 yes

_refine_diff_density_max         0.396
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.080

