# Electronic Supplementary Material (ESI) for MedChemComm.
# 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_VC1400
_database_code_depnum_ccdc_archive 'CCDC 1841095'
_audit_update_record             
;
2018-05-02 deposited with the CCDC.
2018-06-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT026_VC1400              
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        22% Check
RESPONSE: the crystal diffracts very poorly
;
# Added during the CSD deposition process: Wednesday 02 May 2018 10:27 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/1


_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
;
4-chloro-N-(3-(piperidin-1-yl)propyl)quinoline-2-carboxamide
;
_chemical_formula_moiety         'C18 H22 Cl N3 O'
_chemical_formula_sum            'C18 H22 Cl N3 O'
_chemical_formula_weight         331.83

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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   37.512(5)
_cell_length_b                   7.280(5)
_cell_length_c                   12.978(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3544(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    22101
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      27.2

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98342
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_special_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_reflns_number            15689
_diffrn_reflns_av_unetI/netI     0.3501
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.679
_diffrn_reflns_theta_max         29.143
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.744
_diffrn_reflns_point_group_measured_fraction_full 0.862
_reflns_number_total             7097
_reflns_number_gt                1553
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.594
_reflns_Friedel_fraction_max     0.579
_reflns_Friedel_fraction_full    0.711

_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       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction

_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'

_computing_structure_solution    'SHELXS (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0095P)²] where P=(Fo²+2Fc²)/3'
_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 x determined using 399 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7097
_refine_ls_number_parameters     415
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.2630
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.0560
_refine_ls_wR_factor_gt          0.0396
_refine_ls_goodness_of_fit_ref   0.586
_refine_ls_restrained_S_all      0.586
_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
N1A N 0.61359(14) 0.3029(6) 0.9348(4) 0.0442(15) Uani 1 1 d . . . . .
C2A C 0.62731(16) 0.2874(7) 0.8413(6) 0.0376(17) Uani 1 1 d . . . . .
C3A C 0.60685(17) 0.2952(8) 0.7517(5) 0.052(2) Uani 1 1 d . . . . .
H3A H 0.617506 0.283228 0.687378 0.062 Uiso 1 1 calc R U . . .
C4A C 0.5713(2) 0.3206(8) 0.7600(6) 0.058(2) Uani 1 1 d . . . . .
C5A C 0.5550(2) 0.3396(8) 0.8585(7) 0.054(2) Uani 1 1 d . . . . .
C6A C 0.5177(2) 0.3691(8) 0.8755(7) 0.069(2) Uani 1 1 d . . . . .
H6A H 0.501829 0.375566 0.820570 0.083 Uiso 1 1 calc R U . . .
Cl1A Cl 0.54449(4) 0.3248(2) 0.6492(2) 0.0956(7) Uani 1 1 d . . . . .
C7A C 0.5060(2) 0.3874(9) 0.9749(9) 0.096(4) Uani 1 1 d . . . . .
H7A H 0.481833 0.405617 0.986386 0.115 Uiso 1 1 calc R U . . .
C8A C 0.5281(3) 0.3804(10) 1.0571(7) 0.089(3) Uani 1 1 d . . . . .
H8A H 0.519287 0.395411 1.123447 0.107 Uiso 1 1 calc R U . . .
C9A C 0.5640(2) 0.3506(8) 1.0410(7) 0.074(3) Uani 1 1 d . . . . .
H9A H 0.579132 0.344957 1.097586 0.089 Uiso 1 1 calc R U . . .
C10A C 0.5780(2) 0.3287(8) 0.9434(6) 0.050(2) Uani 1 1 d . . . . .
C11A C 0.66674(16) 0.2616(8) 0.8271(6) 0.051(2) Uani 1 1 d . . . . .
O12A O 0.67951(11) 0.2511(5) 0.7407(3) 0.0685(15) Uani 1 1 d . . . . .
N13A N 0.68492(12) 0.2480(6) 0.9142(4) 0.0553(17) Uani 1 1 d . . . . .
H13A H 0.673948 0.257009 0.972163 0.066 Uiso 1 1 calc R U . . .
C14A C 0.72241(16) 0.2189(9) 0.9130(6) 0.091(3) Uani 1 1 d . . . . .
H14A H 0.726748 0.092562 0.892736 0.109 Uiso 1 1 calc R U . . .
H14B H 0.732612 0.296902 0.860060 0.109 Uiso 1 1 calc R U . . .
C15A C 0.7403(2) 0.2508(17) 1.0025(5) 0.194(6) Uani 1 1 d D . . . .
H15A H 0.747914 0.377552 0.996383 0.233 Uiso 1 1 calc R U . . .
H15B H 0.761786 0.178028 0.995660 0.233 Uiso 1 1 calc R U . . .
C16A C 0.73110(19) 0.2327(14) 1.1088(5) 0.130(4) Uani 1 1 d D . . . .
H16A H 0.745727 0.318139 1.147504 0.156 Uiso 1 1 calc R U . . .
H16B H 0.737742 0.109893 1.130594 0.156 Uiso 1 1 calc R U . . .
N17A N 0.69443(17) 0.2624(10) 1.1382(4) 0.0831(18) Uani 1 1 d . . . . .
C18A C 0.6826(2) 0.1083(9) 1.2020(6) 0.099(3) Uani 1 1 d . . . . .
H18A H 0.696596 0.104567 1.264719 0.119 Uiso 1 1 calc R U . . .
H18B H 0.686493 -0.005789 1.165053 0.119 Uiso 1 1 calc R U . . .
C19A C 0.6436(2) 0.1245(10) 1.2293(6) 0.097(3) Uani 1 1 d . . . . .
H19A H 0.636704 0.021278 1.272138 0.117 Uiso 1 1 calc R U . . .
H19B H 0.629423 0.120648 1.166864 0.117 Uiso 1 1 calc R U . . .
C20A C 0.6363(2) 0.3014(11) 1.2861(5) 0.104(3) Uani 1 1 d . . . . .
H20A H 0.648141 0.300031 1.352528 0.125 Uiso 1 1 calc R U . . .
H20B H 0.610893 0.315296 1.297497 0.125 Uiso 1 1 calc R U . . .
C21A C 0.6504(3) 0.4623(10) 1.2205(6) 0.115(3) Uani 1 1 d . . . . .
H21A H 0.636591 0.471303 1.157504 0.139 Uiso 1 1 calc R U . . .
H21B H 0.647571 0.576341 1.258313 0.139 Uiso 1 1 calc R U . . .
C22A C 0.6886(2) 0.4347(10) 1.1948(7) 0.113(3) Uani 1 1 d . . . . .
H22A H 0.696848 0.536965 1.153309 0.135 Uiso 1 1 calc R U . . .
H22B H 0.702441 0.432846 1.257900 0.135 Uiso 1 1 calc R U . . .
N1B N 0.60628(19) 0.7991(7) 0.8472(5) 0.0590(17) Uani 1 1 d . . . . .
C2B C 0.6266(2) 0.7882(8) 0.9266(6) 0.052(2) Uani 1 1 d . . . . .
C3B C 0.61436(18) 0.7994(8) 1.0296(6) 0.062(2) Uani 1 1 d . . . . .
H3B H 0.629734 0.786776 1.085374 0.074 Uiso 1 1 calc R U . . .
C4B C 0.5794(2) 0.8291(8) 1.0423(5) 0.061(2) Uani 1 1 d . . . . .
C5B C 0.5550(2) 0.8436(9) 0.9609(7) 0.052(2) Uani 1 1 d . . . . .
C6B C 0.5182(2) 0.8786(9) 0.9676(7) 0.076(3) Uani 1 1 d . . . . .
H6B H 0.507805 0.891185 1.032245 0.091 Uiso 1 1 calc R U . . .
Cl1B Cl 0.56156(4) 0.8391(2) 1.1675(2) 0.0978(6) Uani 1 1 d . . . . .
C7B C 0.4972(2) 0.8947(9) 0.8819(8) 0.092(3) Uani 1 1 d . . . . .
H7B H 0.472911 0.916499 0.888094 0.111 Uiso 1 1 calc R U . . .
C8B C 0.5130(3) 0.8777(9) 0.7851(8) 0.091(3) Uani 1 1 d . . . . .
H8B H 0.498691 0.890049 0.727062 0.109 Uiso 1 1 calc R U . . .
C9B C 0.5490(2) 0.8434(8) 0.7713(6) 0.071(2) Uani 1 1 d . . . . .
H9B H 0.558750 0.830382 0.705803 0.085 Uiso 1 1 calc R U . . .
C10B C 0.5702(2) 0.8291(8) 0.8601(7) 0.054(2) Uani 1 1 d . . . . .
C11B C 0.6661(2) 0.7571(9) 0.9157(6) 0.062(2) Uani 1 1 d . . . . .
O12B O 0.68589(13) 0.7493(6) 0.9901(4) 0.0848(17) Uani 1 1 d . . . . .
N13B N 0.67676(14) 0.7445(7) 0.8194(5) 0.0730(19) Uani 1 1 d . . . . .
H13B H 0.661030 0.754441 0.771543 0.088 Uiso 1 1 calc R U . . .
C14B C 0.71418(19) 0.7142(10) 0.7891(6) 0.095(3) Uani 1 1 d . . . . .
H14C H 0.729405 0.766655 0.841906 0.114 Uiso 1 1 calc R U . . .
H14D H 0.718578 0.582951 0.787938 0.114 Uiso 1 1 calc R U . . .
C15B C 0.7245(2) 0.7881(12) 0.6927(7) 0.122(3) Uani 1 1 d . . . . .
H15C H 0.750031 0.770377 0.685481 0.146 Uiso 1 1 calc R U . . .
H15D H 0.720328 0.919534 0.694820 0.146 Uiso 1 1 calc R U . . .
C16B C 0.7076(2) 0.7171(14) 0.6004(7) 0.147(4) Uani 1 1 d . . . . .
H16C H 0.711308 0.585298 0.598137 0.177 Uiso 1 1 calc R U . . .
H16D H 0.719513 0.769617 0.540938 0.177 Uiso 1 1 calc R U . . .
N17B N 0.6690(2) 0.7538(10) 0.5913(4) 0.0813(19) Uani 1 1 d . . . . .
C18B C 0.6609(2) 0.9307(11) 0.5432(7) 0.110(3) Uani 1 1 d . . . . .
H18C H 0.670565 0.932883 0.473943 0.132 Uiso 1 1 calc R U . . .
H18D H 0.672136 1.028306 0.582293 0.132 Uiso 1 1 calc R U . . .
C19B C 0.6221(3) 0.9632(10) 0.5389(6) 0.109(3) Uani 1 1 d . . . . .
H19C H 0.617815 1.080405 0.505591 0.131 Uiso 1 1 calc R U . . .
H19D H 0.612986 0.971256 0.608667 0.131 Uiso 1 1 calc R U . . .
C20B C 0.60189(19) 0.8160(12) 0.4819(6) 0.111(3) Uani 1 1 d . . . . .
H20C H 0.607767 0.819956 0.409165 0.133 Uiso 1 1 calc R U . . .
H20D H 0.576442 0.835786 0.489256 0.133 Uiso 1 1 calc R U . . .
C21B C 0.6120(2) 0.6312(10) 0.5265(6) 0.099(3) Uani 1 1 d . . . . .
H21C H 0.601469 0.534285 0.485246 0.119 Uiso 1 1 calc R U . . .
H21D H 0.602679 0.620950 0.595966 0.119 Uiso 1 1 calc R U . . .
C22B C 0.6523(2) 0.6077(11) 0.5286(6) 0.095(3) Uani 1 1 d . . . . .
H22C H 0.658189 0.488542 0.557410 0.114 Uiso 1 1 calc R U . . .
H22D H 0.661540 0.612624 0.458891 0.114 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
N1A C2A 1.322(6) . ?
N1A C10A 1.352(7) . ?
C2A C3A 1.394(8) . ?
C2A C11A 1.503(8) . ?
C3A C4A 1.350(7) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.423(8) . ?
C4A Cl1A 1.756(6) . ?
C5A C10A 1.402(9) . ?
C5A C6A 1.435(8) . ?
C6A C7A 1.368(10) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.352(9) . ?
C7A H7A 0.9300 . ?
C8A C9A 1.376(9) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.381(8) . ?
C9A H9A 0.9300 . ?
C11A O12A 1.222(6) . ?
C11A N13A 1.323(7) . ?
N13A C14A 1.422(6) . ?
N13A H13A 0.8600 . ?
C14A C15A 1.361(9) . ?
C14A H14A 0.9700 . ?
C14A H14B 0.9700 . ?
C15A C16A 1.4274(14) . ?
C15A H15A 0.9700 . ?
C15A H15B 0.9700 . ?
C16A N17A 1.444(8) . ?
C16A H16A 0.9700 . ?
C16A H16B 0.9700 . ?
N17A C18A 1.463(7) . ?
N17A C22A 1.470(8) . ?
C18A C19A 1.508(8) . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C19A C20A 1.509(8) . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C20A C21A 1.541(9) . ?
C20A H20A 0.9700 . ?
C20A H20B 0.9700 . ?
C21A C22A 1.485(8) . ?
C21A H21A 0.9700 . ?
C21A H21B 0.9700 . ?
C22A H22A 0.9700 . ?
C22A H22B 0.9700 . ?
N1B C2B 1.286(7) . ?
N1B C10B 1.379(7) . ?
C2B C3B 1.416(8) . ?
C2B C11B 1.506(9) . ?
C3B C4B 1.338(8) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.404(8) . ?
C4B Cl1B 1.759(6) . ?
C5B C6B 1.405(8) . ?
C5B C10B 1.432(8) . ?
C6B C7B 1.366(9) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.394(9) . ?
C7B H7B 0.9300 . ?
C8B C9B 1.385(8) . ?
C8B H8B 0.9300 . ?
C9B C10B 1.405(8) . ?
C9B H9B 0.9300 . ?
C11B O12B 1.218(7) . ?
C11B N13B 1.314(7) . ?
N13B C14B 1.474(8) . ?
N13B H13B 0.8600 . ?
C14B C15B 1.417(8) . ?
C14B H14C 0.9700 . ?
C14B H14D 0.9700 . ?
C15B C16B 1.450(10) . ?
C15B H15C 0.9700 . ?
C15B H15D 0.9700 . ?
C16B N17B 1.479(9) . ?
C16B H16C 0.9700 . ?
C16B H16D 0.9700 . ?
N17B C18B 1.463(8) . ?
N17B C22B 1.478(8) . ?
C18B C19B 1.474(8) . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?
C19B C20B 1.507(8) . ?
C19B H19C 0.9700 . ?
C19B H19D 0.9700 . ?
C20B C21B 1.513(8) . ?
C20B H20C 0.9700 . ?
C20B H20D 0.9700 . ?
C21B C22B 1.520(8) . ?
C21B H21C 0.9700 . ?
C21B H21D 0.9700 . ?
C22B H22C 0.9700 . ?
C22B H22D 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
C2A N1A C10A 118.2(6) . . ?
N1A C2A C3A 123.2(6) . . ?
N1A C2A C11A 120.4(6) . . ?
C3A C2A C11A 116.4(7) . . ?
C4A C3A C2A 118.8(7) . . ?
C4A C3A H3A 120.6 . . ?
C2A C3A H3A 120.6 . . ?
C3A C4A C5A 120.6(7) . . ?
C3A C4A Cl1A 120.2(7) . . ?
C5A C4A Cl1A 119.2(6) . . ?
C10A C5A C4A 115.9(7) . . ?
C10A C5A C6A 119.2(8) . . ?
C4A C5A C6A 124.9(9) . . ?
C7A C6A C5A 118.2(8) . . ?
C7A C6A H6A 120.9 . . ?
C5A C6A H6A 120.9 . . ?
C8A C7A C6A 123.0(9) . . ?
C8A C7A H7A 118.5 . . ?
C6A C7A H7A 118.5 . . ?
C7A C8A C9A 119.0(9) . . ?
C7A C8A H8A 120.5 . . ?
C9A C8A H8A 120.5 . . ?
C8A C9A C10A 122.0(8) . . ?
C8A C9A H9A 119.0 . . ?
C10A C9A H9A 119.0 . . ?
N1A C10A C9A 118.0(8) . . ?
N1A C10A C5A 123.3(7) . . ?
C9A C10A C5A 118.7(8) . . ?
O12A C11A N13A 125.3(6) . . ?
O12A C11A C2A 120.4(7) . . ?
N13A C11A C2A 114.3(6) . . ?
C11A N13A C14A 120.7(6) . . ?
C11A N13A H13A 119.6 . . ?
C14A N13A H13A 119.6 . . ?
C15A C14A N13A 116.8(7) . . ?
C15A C14A H14A 108.1 . . ?
N13A C14A H14A 108.1 . . ?
C15A C14A H14B 108.1 . . ?
N13A C14A H14B 108.1 . . ?
H14A C14A H14B 107.3 . . ?
C14A C15A C16A 133.7(9) . . ?
C14A C15A H15A 103.8 . . ?
C16A C15A H15A 103.8 . . ?
C14A C15A H15B 103.8 . . ?
C16A C15A H15B 103.8 . . ?
H15A C15A H15B 105.4 . . ?
C15A C16A N17A 118.1(7) . . ?
C15A C16A H16A 107.8 . . ?
N17A C16A H16A 107.8 . . ?
C15A C16A H16B 107.8 . . ?
N17A C16A H16B 107.8 . . ?
H16A C16A H16B 107.1 . . ?
C16A N17A C18A 108.9(7) . . ?
C16A N17A C22A 113.7(8) . . ?
C18A N17A C22A 109.0(6) . . ?
N17A C18A C19A 111.6(6) . . ?
N17A C18A H18A 109.3 . . ?
C19A C18A H18A 109.3 . . ?
N17A C18A H18B 109.3 . . ?
C19A C18A H18B 109.3 . . ?
H18A C18A H18B 108.0 . . ?
C18A C19A C20A 111.0(6) . . ?
C18A C19A H19A 109.4 . . ?
C20A C19A H19A 109.4 . . ?
C18A C19A H19B 109.4 . . ?
C20A C19A H19B 109.4 . . ?
H19A C19A H19B 108.0 . . ?
C19A C20A C21A 108.5(6) . . ?
C19A C20A H20A 110.0 . . ?
C21A C20A H20A 110.0 . . ?
C19A C20A H20B 110.0 . . ?
C21A C20A H20B 110.0 . . ?
H20A C20A H20B 108.4 . . ?
C22A C21A C20A 110.6(7) . . ?
C22A C21A H21A 109.5 . . ?
C20A C21A H21A 109.5 . . ?
C22A C21A H21B 109.5 . . ?
C20A C21A H21B 109.5 . . ?
H21A C21A H21B 108.1 . . ?
N17A C22A C21A 111.8(7) . . ?
N17A C22A H22A 109.3 . . ?
C21A C22A H22A 109.3 . . ?
N17A C22A H22B 109.3 . . ?
C21A C22A H22B 109.3 . . ?
H22A C22A H22B 107.9 . . ?
C2B N1B C10B 119.6(7) . . ?
N1B C2B C3B 124.1(7) . . ?
N1B C2B C11B 121.2(7) . . ?
C3B C2B C11B 114.7(7) . . ?
C4B C3B C2B 116.3(7) . . ?
C4B C3B H3B 121.8 . . ?
C2B C3B H3B 121.8 . . ?
C3B C4B C5B 124.0(7) . . ?
C3B C4B Cl1B 119.5(7) . . ?
C5B C4B Cl1B 116.3(7) . . ?
C4B C5B C6B 127.5(9) . . ?
C4B C5B C10B 114.8(7) . . ?
C6B C5B C10B 117.6(8) . . ?
C7B C6B C5B 122.0(9) . . ?
C7B C6B H6B 119.0 . . ?
C5B C6B H6B 119.0 . . ?
C6B C7B C8B 118.8(9) . . ?
C6B C7B H7B 120.6 . . ?
C8B C7B H7B 120.6 . . ?
C9B C8B C7B 123.1(9) . . ?
C9B C8B H8B 118.4 . . ?
C7B C8B H8B 118.4 . . ?
C8B C9B C10B 117.4(8) . . ?
C8B C9B H9B 121.3 . . ?
C10B C9B H9B 121.3 . . ?
N1B C10B C9B 117.9(9) . . ?
N1B C10B C5B 121.0(8) . . ?
C9B C10B C5B 121.1(8) . . ?
O12B C11B N13B 124.5(8) . . ?
O12B C11B C2B 122.1(7) . . ?
N13B C11B C2B 113.5(7) . . ?
C11B N13B C14B 123.5(7) . . ?
C11B N13B H13B 118.2 . . ?
C14B N13B H13B 118.2 . . ?
C15B C14B N13B 116.1(7) . . ?
C15B C14B H14C 108.3 . . ?
N13B C14B H14C 108.3 . . ?
C15B C14B H14D 108.3 . . ?
N13B C14B H14D 108.3 . . ?
H14C C14B H14D 107.4 . . ?
C14B C15B C16B 118.3(8) . . ?
C14B C15B H15C 107.7 . . ?
C16B C15B H15C 107.7 . . ?
C14B C15B H15D 107.7 . . ?
C16B C15B H15D 107.7 . . ?
H15C C15B H15D 107.1 . . ?
C15B C16B N17B 115.5(8) . . ?
C15B C16B H16C 108.4 . . ?
N17B C16B H16C 108.4 . . ?
C15B C16B H16D 108.4 . . ?
N17B C16B H16D 108.4 . . ?
H16C C16B H16D 107.5 . . ?
C18B N17B C22B 108.1(6) . . ?
C18B N17B C16B 113.4(7) . . ?
C22B N17B C16B 109.2(7) . . ?
N17B C18B C19B 111.3(7) . . ?
N17B C18B H18C 109.4 . . ?
C19B C18B H18C 109.4 . . ?
N17B C18B H18D 109.4 . . ?
C19B C18B H18D 109.4 . . ?
H18C C18B H18D 108.0 . . ?
C18B C19B C20B 113.7(7) . . ?
C18B C19B H19C 108.8 . . ?
C20B C19B H19C 108.8 . . ?
C18B C19B H19D 108.8 . . ?
C20B C19B H19D 108.8 . . ?
H19C C19B H19D 107.7 . . ?
C19B C20B C21B 108.5(6) . . ?
C19B C20B H20C 110.0 . . ?
C21B C20B H20C 110.0 . . ?
C19B C20B H20D 110.0 . . ?
C21B C20B H20D 110.0 . . ?
H20C C20B H20D 108.4 . . ?
C20B C21B C22B 110.9(6) . . ?
C20B C21B H21C 109.5 . . ?
C22B C21B H21C 109.5 . . ?
C20B C21B H21D 109.5 . . ?
C22B C21B H21D 109.5 . . ?
H21C C21B H21D 108.0 . . ?
N17B C22B C21B 110.5(6) . . ?
N17B C22B H22C 109.6 . . ?
C21B C22B H22C 109.6 . . ?
N17B C22B H22D 109.6 . . ?
C21B C22B H22D 109.6 . . ?
H22C C22B H22D 108.1 . . ?

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
C10A N1A C2A C3A -0.4(9) . . . . ?
C10A N1A C2A C11A 179.0(5) . . . . ?
N1A C2A C3A C4A 0.3(10) . . . . ?
C11A C2A C3A C4A -179.2(6) . . . . ?
C2A C3A C4A C5A 0.2(10) . . . . ?
C2A C3A C4A Cl1A -178.2(4) . . . . ?
C3A C4A C5A C10A -0.5(9) . . . . ?
Cl1A C4A C5A C10A 177.9(5) . . . . ?
C3A C4A C5A C6A 179.2(6) . . . . ?
Cl1A C4A C5A C6A -2.4(8) . . . . ?
C10A C5A C6A C7A 0.7(9) . . . . ?
C4A C5A C6A C7A -179.0(6) . . . . ?
C5A C6A C7A C8A 0.5(11) . . . . ?
C6A C7A C8A C9A -1.0(13) . . . . ?
C7A C8A C9A C10A 0.4(12) . . . . ?
C2A N1A C10A C9A -178.0(6) . . . . ?
C2A N1A C10A C5A 0.0(9) . . . . ?
C8A C9A C10A N1A 178.9(7) . . . . ?
C8A C9A C10A C5A 0.8(10) . . . . ?
C4A C5A C10A N1A 0.4(9) . . . . ?
C6A C5A C10A N1A -179.4(6) . . . . ?
C4A C5A C10A C9A 178.4(6) . . . . ?
C6A C5A C10A C9A -1.3(9) . . . . ?
N1A C2A C11A O12A -178.4(5) . . . . ?
C3A C2A C11A O12A 1.0(9) . . . . ?
N1A C2A C11A N13A 2.9(9) . . . . ?
C3A C2A C11A N13A -177.6(5) . . . . ?
O12A C11A N13A C14A -0.1(10) . . . . ?
C2A C11A N13A C14A 178.5(5) . . . . ?
C11A N13A C14A C15A 164.5(8) . . . . ?
N13A C14A C15A C16A 32.1(18) . . . . ?
C14A C15A C16A N17A -32(2) . . . . ?
C15A C16A N17A C18A 130.1(10) . . . . ?
C15A C16A N17A C22A -108.1(11) . . . . ?
C16A N17A C18A C19A -176.1(7) . . . . ?
C22A N17A C18A C19A 59.3(8) . . . . ?
N17A C18A C19A C20A -58.4(9) . . . . ?
C18A C19A C20A C21A 54.4(8) . . . . ?
C19A C20A C21A C22A -54.8(9) . . . . ?
C16A N17A C22A C21A 178.2(7) . . . . ?
C18A N17A C22A C21A -60.0(8) . . . . ?
C20A C21A C22A N17A 58.6(9) . . . . ?
C10B N1B C2B C3B 2.1(10) . . . . ?
C10B N1B C2B C11B -179.5(6) . . . . ?
N1B C2B C3B C4B -2.2(10) . . . . ?
C11B C2B C3B C4B 179.2(6) . . . . ?
C2B C3B C4B C5B 2.0(10) . . . . ?
C2B C3B C4B Cl1B 178.4(4) . . . . ?
C3B C4B C5B C6B -178.4(7) . . . . ?
Cl1B C4B C5B C6B 5.0(10) . . . . ?
C3B C4B C5B C10B -1.6(10) . . . . ?
Cl1B C4B C5B C10B -178.1(4) . . . . ?
C4B C5B C6B C7B 178.1(7) . . . . ?
C10B C5B C6B C7B 1.4(11) . . . . ?
C5B C6B C7B C8B -0.7(12) . . . . ?
C6B C7B C8B C9B 0.7(12) . . . . ?
C7B C8B C9B C10B -1.3(11) . . . . ?
C2B N1B C10B C9B 178.9(6) . . . . ?
C2B N1B C10B C5B -1.7(10) . . . . ?
C8B C9B C10B N1B -178.6(6) . . . . ?
C8B C9B C10B C5B 2.0(9) . . . . ?
C4B C5B C10B N1B 1.4(9) . . . . ?
C6B C5B C10B N1B 178.5(6) . . . . ?
C4B C5B C10B C9B -179.2(6) . . . . ?
C6B C5B C10B C9B -2.0(9) . . . . ?
N1B C2B C11B O12B 178.8(6) . . . . ?
C3B C2B C11B O12B -2.6(10) . . . . ?
N1B C2B C11B N13B 0.4(10) . . . . ?
C3B C2B C11B N13B 179.0(5) . . . . ?
O12B C11B N13B C14B 1.6(11) . . . . ?
C2B C11B N13B C14B 180.0(6) . . . . ?
C11B N13B C14B C15B -150.8(7) . . . . ?
N13B C14B C15B C16B -63.6(11) . . . . ?
C14B C15B C16B N17B 65.2(12) . . . . ?
C15B C16B N17B C18B 87.1(10) . . . . ?
C15B C16B N17B C22B -152.2(8) . . . . ?
C22B N17B C18B C19B 60.5(8) . . . . ?
C16B N17B C18B C19B -178.2(7) . . . . ?
N17B C18B C19B C20B -57.6(10) . . . . ?
C18B C19B C20B C21B 52.2(9) . . . . ?
C19B C20B C21B C22B -52.2(9) . . . . ?
C18B N17B C22B C21B -61.7(7) . . . . ?
C16B N17B C22B C21B 174.5(7) . . . . ?
C20B C21B C22B N17B 59.2(8) . . . . ?

_refine_diff_density_max         0.128
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.027


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_VC1439
_database_code_depnum_ccdc_archive 'CCDC 1841096'
_audit_update_record             
;
2018-05-02 deposited with the CCDC.
2018-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1


_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
;
N-((1-butylpiperidin-4-yl)methyl)-8-hydroxyquinoline-2-carboxamide hydrate
;

_chemical_formula_moiety         'C20 H27 N3 O2, H2 O'
_chemical_formula_sum            'C20 H29 N3 O3'
_chemical_formula_weight         359.46

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'
O O 0.0106 0.0060 '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'

_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                   11.3833(6)
_cell_length_b                   11.7128(6)
_cell_length_c                   15.0977(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.830(6)
_cell_angle_gamma                90
_cell_volume                     1954.62(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2341
_cell_measurement_theta_min      2.5285
_cell_measurement_theta_max      29.0072

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_min  0.98515
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0827
_diffrn_reflns_number            8583
_diffrn_reflns_av_unetI/netI     0.0856
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.534
_diffrn_reflns_theta_max         29.071
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4463
_reflns_number_gt                1828
_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, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0444P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4463
_refine_ls_number_parameters     268
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0853
_refine_ls_goodness_of_fit_ref   0.766
_refine_ls_restrained_S_all      0.791
_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
N1 N 0.71875(11) 0.19173(11) 0.69008(9) 0.0444(4) Uani 1 1 d . . . . .
C2 C 0.75573(15) 0.10987(15) 0.75042(11) 0.0466(4) Uani 1 1 d . . . . .
C3 C 0.87606(17) 0.07156(16) 0.77490(12) 0.0602(5) Uani 1 1 d . . . . .
H3 H 0.898558 0.012905 0.817071 0.072 Uiso 1 1 calc R U . . .
C4 C 0.95919(16) 0.12156(17) 0.73598(13) 0.0647(5) Uani 1 1 d . . . . .
H4 H 1.039233 0.097187 0.751970 0.078 Uiso 1 1 calc R U . . .
C5 C 0.92526(16) 0.20973(16) 0.67181(12) 0.0529(5) Uani 1 1 d . . . . .
C6 C 1.00519(17) 0.26603(18) 0.62835(14) 0.0659(5) Uani 1 1 d . . . . .
H6 H 1.086882 0.247090 0.642064 0.079 Uiso 1 1 calc R U . . .
C7 C 0.96109(19) 0.34856(18) 0.56598(14) 0.0677(6) Uani 1 1 d . . . . .
H7 H 1.014012 0.385139 0.536948 0.081 Uiso 1 1 calc R U . . .
C8 C 0.83934(18) 0.38059(15) 0.54380(12) 0.0593(5) Uani 1 1 d . . . . .
H8 H 0.812422 0.437499 0.500782 0.071 Uiso 1 1 calc R U . . .
C9 C 0.76039(17) 0.32820(15) 0.58538(12) 0.0491(4) Uani 1 1 d . . . . .
O1 O 0.64281(10) 0.35979(10) 0.56473(8) 0.0613(4) Uani 1 1 d . . . . .
H1 H 0.606313 0.322957 0.595829 0.092 Uiso 1 1 calc R U . . .
C10 C 0.80179(15) 0.24106(14) 0.65053(11) 0.0449(4) Uani 1 1 d . . . . .
C11 C 0.66402(16) 0.05828(15) 0.79516(11) 0.0475(4) Uani 1 1 d . . . . .
O2 O 0.69152(11) -0.02435(10) 0.84703(8) 0.0640(4) Uani 1 1 d . . . . .
N12 N 0.55623(13) 0.10797(12) 0.77664(9) 0.0520(4) Uani 1 1 d . . . . .
H12 H 0.540679 0.160091 0.735368 0.062 Uiso 1 1 calc R U . . .
C13 C 0.46335(16) 0.07707(15) 0.82399(12) 0.0563(5) Uani 1 1 d . . . . .
H13A H 0.502059 0.048234 0.884106 0.068 Uiso 1 1 calc R U . . .
H13B H 0.414207 0.016109 0.790702 0.068 Uiso 1 1 calc R U . . .
C14 C 0.38164(14) 0.17655(14) 0.83406(11) 0.0490(4) Uani 1 1 d . . . . .
H14 H 0.333728 0.198348 0.773495 0.059 Uiso 1 1 calc R U . . .
C15 C 0.29595(14) 0.13765(15) 0.89209(12) 0.0569(5) Uani 1 1 d . . . . .
H15A H 0.242811 0.078701 0.859651 0.068 Uiso 1 1 calc R U . . .
H15B H 0.342818 0.104885 0.948538 0.068 Uiso 1 1 calc R U . . .
C16 C 0.22016(16) 0.23553(17) 0.91399(13) 0.0662(6) Uani 1 1 d . . . . .
H16A H 0.169364 0.265299 0.857813 0.079 Uiso 1 1 calc R U . . .
H16B H 0.167824 0.207595 0.951358 0.079 Uiso 1 1 calc R U . . .
N17 N 0.29649(13) 0.32700(12) 0.96228(9) 0.0549(4) Uani 1 1 d . . . . .
C18 C 0.36994(16) 0.37099(15) 0.90189(12) 0.0588(5) Uani 1 1 d . . . . .
H18A H 0.418691 0.434393 0.931516 0.071 Uiso 1 1 calc R U . . .
H18B H 0.316868 0.399265 0.846097 0.071 Uiso 1 1 calc R U . . .
C19 C 0.45209(15) 0.27977(14) 0.87860(11) 0.0525(5) Uani 1 1 d . . . . .
H19A H 0.509535 0.256002 0.933887 0.063 Uiso 1 1 calc R U . . .
H19B H 0.497420 0.311591 0.837601 0.063 Uiso 1 1 calc R U . . .
C20 C 0.21975(18) 0.41785(18) 0.98744(15) 0.0790(7) Uani 1 1 d D . . . .
H20A H 0.163197 0.383884 1.018717 0.095 Uiso 0.725(6) 1 calc R U P A 1
H20B H 0.173354 0.454337 0.932465 0.095 Uiso 0.725(6) 1 calc R U P A 1
H20C H 0.197440 0.467753 0.934818 0.095 Uiso 0.275(6) 1 calc R U P A 2
H20D H 0.145803 0.380642 0.993193 0.095 Uiso 0.275(6) 1 calc R U P A 2
C21A C 0.2963(4) 0.5085(3) 1.0496(3) 0.0858(11) Uani 0.725(6) 1 d D . P A 1
H21A H 0.346979 0.547056 1.015633 0.103 Uiso 0.725(6) 1 calc R U P A 1
H21B H 0.349355 0.470112 1.100826 0.103 Uiso 0.725(6) 1 calc R U P A 1
C22A C 0.2212(4) 0.5996(4) 1.0870(3) 0.1038(16) Uani 0.725(6) 1 d D . P A 1
H22A H 0.277648 0.655136 1.120896 0.125 Uiso 0.725(6) 1 calc R U P A 1
H22B H 0.171517 0.639257 1.034901 0.125 Uiso 0.725(6) 1 calc R U P A 1
C23A C 0.1455(4) 0.5659(5) 1.1426(3) 0.1227(19) Uani 0.725(6) 1 d D . P A 1
H23A H 0.192130 0.526689 1.195118 0.184 Uiso 0.725(6) 1 calc R U P A 1
H23B H 0.083928 0.515860 1.109014 0.184 Uiso 0.725(6) 1 calc R U P A 1
H23C H 0.108311 0.632059 1.161747 0.184 Uiso 0.725(6) 1 calc R U P A 1
C21B C 0.2545(9) 0.4893(10) 1.0633(8) 0.0858(11) Uani 0.275(6) 1 d D . P A 2
H21C H 0.320463 0.538897 1.057391 0.103 Uiso 0.275(6) 1 calc R U P A 2
H21D H 0.279589 0.445131 1.118939 0.103 Uiso 0.275(6) 1 calc R U P A 2
C22B C 0.1420(9) 0.5578(7) 1.0633(5) 0.064(3) Uani 0.275(6) 1 d D . P A 2
H22C H 0.109117 0.592095 1.004101 0.077 Uiso 0.275(6) 1 calc R U P A 2
H22D H 0.080463 0.510442 1.079566 0.077 Uiso 0.275(6) 1 calc R U P A 2
C23B C 0.1853(11) 0.6443(8) 1.1321(8) 0.115(5) Uani 0.275(6) 1 d D . P A 2
H23D H 0.247520 0.612503 1.180158 0.173 Uiso 0.275(6) 1 calc R U P A 2
H23E H 0.119496 0.670097 1.156582 0.173 Uiso 0.275(6) 1 calc R U P A 2
H23F H 0.217475 0.707533 1.105011 0.173 Uiso 0.275(6) 1 calc R U P A 2
OW1 O 0.44286(12) 0.27704(14) 0.62556(10) 0.0596(4) Uani 1 1 d . . . . .
HW1 H 0.4106(19) 0.336(2) 0.6350(15) 0.104(9) Uiso 1 1 d . . . . .
HW2 H 0.401(2) 0.242(2) 0.5741(15) 0.114(10) 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 C2 1.3203(19) . ?
N1 C10 1.3615(18) . ?
C2 C3 1.404(2) . ?
C2 C11 1.499(2) . ?
C3 C4 1.360(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.405(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.407(2) . ?
C5 C10 1.413(2) . ?
C6 C7 1.359(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.397(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.359(2) . ?
C8 H8 0.9300 . ?
C9 O1 1.3512(19) . ?
C9 C10 1.418(2) . ?
O1 H1 0.8200 . ?
C11 O2 1.2373(18) . ?
C11 N12 1.326(2) . ?
N12 C13 1.4564(18) . ?
N12 H12 0.8600 . ?
C13 C14 1.521(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C19 1.516(2) . ?
C14 C15 1.528(2) . ?
C14 H14 0.9800 . ?
C15 C16 1.518(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N17 1.460(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
N17 C18 1.4697(18) . ?
N17 C20 1.483(2) . ?
C18 C19 1.516(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21B 1.397(9) . ?
C20 C21A 1.542(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C20 H20D 0.9700 . ?
C21A C22A 1.556(4) . ?
C21A H21A 0.9700 . ?
C21A H21B 0.9700 . ?
C22A C23A 1.396(5) . ?
C22A H22A 0.9700 . ?
C22A H22B 0.9700 . ?
C23A H23A 0.9600 . ?
C23A H23B 0.9600 . ?
C23A H23C 0.9600 . ?
C21B C22B 1.511(9) . ?
C21B H21C 0.9700 . ?
C21B H21D 0.9700 . ?
C22B C23B 1.450(9) . ?
C22B H22C 0.9700 . ?
C22B H22D 0.9700 . ?
C23B H23D 0.9600 . ?
C23B H23E 0.9600 . ?
C23B H23F 0.9600 . ?
OW1 HW1 0.82(2) . ?
OW1 HW2 0.91(2) . ?

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
C2 N1 C10 118.07(14) . . ?
N1 C2 C3 122.94(15) . . ?
N1 C2 C11 117.51(15) . . ?
C3 C2 C11 119.54(17) . . ?
C4 C3 C2 118.96(18) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 120.62(17) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 124.35(18) . . ?
C4 C5 C10 116.23(16) . . ?
C6 C5 C10 119.42(19) . . ?
C7 C6 C5 118.93(18) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C8 122.55(18) . . ?
C6 C7 H7 118.7 . . ?
C8 C7 H7 118.7 . . ?
C9 C8 C7 119.71(19) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
O1 C9 C8 119.84(17) . . ?
O1 C9 C10 120.26(15) . . ?
C8 C9 C10 119.90(17) . . ?
C9 O1 H1 109.5 . . ?
N1 C10 C5 123.17(17) . . ?
N1 C10 C9 117.34(15) . . ?
C5 C10 C9 119.49(16) . . ?
O2 C11 N12 123.93(16) . . ?
O2 C11 C2 120.15(16) . . ?
N12 C11 C2 115.91(16) . . ?
C11 N12 C13 122.09(14) . . ?
C11 N12 H12 119.0 . . ?
C13 N12 H12 119.0 . . ?
N12 C13 C14 113.06(13) . . ?
N12 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
N12 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C19 C14 C13 112.58(14) . . ?
C19 C14 C15 109.02(13) . . ?
C13 C14 C15 108.56(14) . . ?
C19 C14 H14 108.9 . . ?
C13 C14 H14 108.9 . . ?
C15 C14 H14 108.9 . . ?
C16 C15 C14 111.94(14) . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
N17 C16 C15 111.20(13) . . ?
N17 C16 H16A 109.4 . . ?
C15 C16 H16A 109.4 . . ?
N17 C16 H16B 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C16 N17 C18 107.84(13) . . ?
C16 N17 C20 109.74(15) . . ?
C18 N17 C20 111.39(13) . . ?
N17 C18 C19 111.77(13) . . ?
N17 C18 H18A 109.3 . . ?
C19 C18 H18A 109.3 . . ?
N17 C18 H18B 109.3 . . ?
C19 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 C14 112.00(14) . . ?
C18 C19 H19A 109.2 . . ?
C14 C19 H19A 109.2 . . ?
C18 C19 H19B 109.2 . . ?
C14 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C21B C20 N17 124.8(5) . . ?
N17 C20 C21A 111.6(2) . . ?
N17 C20 H20A 109.3 . . ?
C21A C20 H20A 109.3 . . ?
N17 C20 H20B 109.3 . . ?
C21A C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
C21B C20 H20C 106.1 . . ?
N17 C20 H20C 106.1 . . ?
C21B C20 H20D 106.1 . . ?
N17 C20 H20D 106.1 . . ?
H20C C20 H20D 106.3 . . ?
C20 C21A C22A 114.4(3) . . ?
C20 C21A H21A 108.7 . . ?
C22A C21A H21A 108.7 . . ?
C20 C21A H21B 108.7 . . ?
C22A C21A H21B 108.7 . . ?
H21A C21A H21B 107.6 . . ?
C23A C22A C21A 119.7(4) . . ?
C23A C22A H22A 107.4 . . ?
C21A C22A H22A 107.4 . . ?
C23A C22A H22B 107.4 . . ?
C21A C22A H22B 107.4 . . ?
H22A C22A H22B 106.9 . . ?
C22A C23A H23A 109.5 . . ?
C22A C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
C22A C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
C20 C21B C22B 104.1(7) . . ?
C20 C21B H21C 110.9 . . ?
C22B C21B H21C 110.9 . . ?
C20 C21B H21D 110.9 . . ?
C22B C21B H21D 110.9 . . ?
H21C C21B H21D 108.9 . . ?
C23B C22B C21B 103.2(8) . . ?
C23B C22B H22C 111.1 . . ?
C21B C22B H22C 111.1 . . ?
C23B C22B H22D 111.1 . . ?
C21B C22B H22D 111.1 . . ?
H22C C22B H22D 109.1 . . ?
C22B C23B H23D 109.5 . . ?
C22B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
C22B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
HW1 OW1 HW2 112(2) . . ?

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
C10 N1 C2 C3 -0.3(2) . . . . ?
C10 N1 C2 C11 178.53(13) . . . . ?
N1 C2 C3 C4 0.9(3) . . . . ?
C11 C2 C3 C4 -177.91(15) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 179.99(18) . . . . ?
C3 C4 C5 C10 -0.6(2) . . . . ?
C4 C5 C6 C7 178.66(16) . . . . ?
C10 C5 C6 C7 -0.7(3) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C7 C8 C9 O1 179.34(15) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
C2 N1 C10 C5 -0.8(2) . . . . ?
C2 N1 C10 C9 179.53(13) . . . . ?
C4 C5 C10 N1 1.2(2) . . . . ?
C6 C5 C10 N1 -179.33(14) . . . . ?
C4 C5 C10 C9 -179.08(14) . . . . ?
C6 C5 C10 C9 0.4(2) . . . . ?
O1 C9 C10 N1 0.2(2) . . . . ?
C8 C9 C10 N1 179.90(15) . . . . ?
O1 C9 C10 C5 -179.50(15) . . . . ?
C8 C9 C10 C5 0.2(2) . . . . ?
N1 C2 C11 O2 174.60(14) . . . . ?
C3 C2 C11 O2 -6.5(2) . . . . ?
N1 C2 C11 N12 -6.6(2) . . . . ?
C3 C2 C11 N12 172.27(14) . . . . ?
O2 C11 N12 C13 6.9(2) . . . . ?
C2 C11 N12 C13 -171.86(13) . . . . ?
C11 N12 C13 C14 148.43(15) . . . . ?
N12 C13 C14 C19 -53.95(19) . . . . ?
N12 C13 C14 C15 -174.75(14) . . . . ?
C19 C14 C15 C16 50.93(19) . . . . ?
C13 C14 C15 C16 173.90(15) . . . . ?
C14 C15 C16 N17 -58.42(19) . . . . ?
C15 C16 N17 C18 61.87(17) . . . . ?
C15 C16 N17 C20 -176.62(14) . . . . ?
C16 N17 C18 C19 -61.62(18) . . . . ?
C20 N17 C18 C19 177.91(16) . . . . ?
N17 C18 C19 C14 57.52(19) . . . . ?
C13 C14 C19 C18 -170.92(13) . . . . ?
C15 C14 C19 C18 -50.39(18) . . . . ?
C16 N17 C20 C21B 150.8(7) . . . . ?
C18 N17 C20 C21B -89.9(7) . . . . ?
C16 N17 C20 C21A 172.4(2) . . . . ?
C18 N17 C20 C21A -68.3(3) . . . . ?
N17 C20 C21A C22A -173.9(3) . . . . ?
C20 C21A C22A C23A 61.7(7) . . . . ?
N17 C20 C21B C22B -174.8(5) . . . . ?
C20 C21B C22B C23B -170.4(10) . . . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.029

