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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_alxs101
_database_code_depnum_ccdc_archive 'CCDC 1422248'
_audit_update_record             
;
2015-09-03 deposited with the CCDC.
2016-01-13 downloaded from the CCDC.
;

#  The final refinement of this structure was carried out at 
#  Brandeis University.  The structure was refined (full-matrix-
#  least squares) using the Oxford University Crystals for Windows 
#  program. All non-hydrogen atoms were refined using anisotropic 
#  displacement parameters.  After location of H atoms on electron-
#  density difference maps, the H atoms attached to ordered atoms 
#  were initially refined with soft restraints on the bond lengths 
#  and angles to regularize their geometry (C---H in the range 
#  0.93--0.98 \%A and Uiso (H) in the range 1.2-1.5 times Ueq of 
#  the parent atom), after which the positions were refined with 
#  riding constraints.2  Inspection of the ADPs for atoms C(26) 
#  and C(27) strongly indicated disorder; accordingly, these were 
#  split and refined, using ADPs for the C(270)/C(271) pair and 
#  isotropic displacement parameters for the C(260)/C(261) pair.  
#  The occupancies of the two ring orientations [C(260)/C(270) and 
#  C(261)/C(271)] were constrained to sum to 1.0.  Populations 
#  of the two components are equal within experimental error 
#  [0.500(11)].  The final least-squares refinement converged 
#  to R1 = 0.0345 (I > 2?(I), 3118 data) and wR2 = 0.0824 
#  (F2, 3931 data, 280 parameters).

_audit_creation_date             2013-09-20
_audit_creation_method           CRYSTALS_ver_14.52

_oxford_structure_analysis_title 'alxs0101 P 21/n R = 0.04'
_chemical_name_systematic        
7-(4-(4-(2,3-Dichlorophenyl)-1-piperazinyl)butoxy)-3,4-dihydro-2(1H)-quinolinone
_chemical_melting_point          400

_cell_length_a                   16.6133(10)
_cell_length_b                   6.9533(4)
_cell_length_c                   19.4632(11)
_cell_angle_alpha                90
_cell_angle_beta                 106.9900(10)
_cell_angle_gamma                90
_cell_volume                     2150.2(2)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C23 H27 Cl2 N3 O2 
# Dc =      1.39 Fooo =    944.00 Mu =      3.28 M =    448.39
# Found Formula = C23 H27 Cl2 N3 O2 
# Dc =      1.39 FOOO =    944.00 Mu =      3.28 M =    448.39

_chemical_formula_sum            'C23 H27 Cl2 N3 O2'
_chemical_formula_moiety         'C23 H27 Cl2 N3 O2'
_chemical_compound_source        ?
_chemical_formula_weight         448.39


_cell_measurement_reflns_used    7392
_cell_measurement_theta_min      2
_cell_measurement_theta_max      25
_cell_measurement_temperature    173

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.070
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_max          0.280

_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.328

# Sheldrick geometric approximatio 0.93 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'Bruker SMART'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SMART (Siemens, 1993)'
_computing_cell_refinement       'SAINT (Siemens ,1995)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      173
_diffrn_reflns_number            17022
_reflns_number_total             3931
_diffrn_reflns_av_R_equivalents  0.036
# Number of reflections without Friedels Law is 3931 
# Number of reflections with Friedels Law is 0 
# Theoretical number of reflections is about 3954 


_diffrn_reflns_theta_min         1.913
_diffrn_reflns_theta_max         25.387
_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        25.387
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       23
_reflns_limit_h_min              -19
_reflns_limit_h_max              18
_reflns_limit_k_min              0
_reflns_limit_k_max              8
_reflns_limit_l_min              0
_reflns_limit_l_max              23

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.38
_refine_diff_density_max         0.30


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         3931
_refine_ls_number_restraints     0
_refine_ls_number_parameters     280
_oxford_refine_ls_R_factor_ref   0.0462
_refine_ls_wR_factor_ref         0.0824
_refine_ls_goodness_of_fit_ref   0.9636
_refine_ls_shift/su_max          0.0006796
_refine_ls_shift/su_mean         0.0000401


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3931
_refine_ls_R_factor_all          0.0462
_refine_ls_wR_factor_all         0.0824

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3118
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_gt          0.0767

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.03P)² + 1.20P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Cl1 Cl 0.56619(3) 1.10860(7) 0.35826(3) 0.0395 1.0000 Uani . . . . . .
Cl2 Cl 0.76021(3) 1.04959(8) 0.43200(3) 0.0411 1.0000 Uani . . . . . .
O17 O 0.06477(8) 0.24067(18) 0.37702(6) 0.0314 1.0000 Uani . . . . . .
O28 O -0.09803(8) -0.62774(19) 0.45713(7) 0.0368 1.0000 Uani . . . . . .
N1 N 0.28234(9) 0.7976(2) 0.37052(7) 0.0254 1.0000 Uani . . . . . .
N4 N 0.45749(9) 0.7880(2) 0.37747(7) 0.0259 1.0000 Uani . . . . . .
N24 N -0.05415(10) -0.3426(2) 0.42705(8) 0.0358 1.0000 Uani . . . . . .
H241 H -0.0154 -0.3400 0.4677 0.0441 1.0000 Uiso R . . . . .
C2 C 0.31348(11) 0.6830(3) 0.32085(9) 0.0287 1.0000 Uani . . . . . .
H22 H 0.3092 0.7546 0.2764 0.0351 1.0000 Uiso R . . . . .
H21 H 0.2783 0.5684 0.3066 0.0340 1.0000 Uiso R . . . . .
C3 C 0.40322(11) 0.6197(3) 0.35643(10) 0.0292 1.0000 Uani . . . . . .
H32 H 0.4036 0.5355 0.3978 0.0341 1.0000 Uiso R . . . . .
H31 H 0.4240 0.5435 0.3244 0.0344 1.0000 Uiso R . . . . .
C5 C 0.42570(11) 0.9100(3) 0.42560(9) 0.0288 1.0000 Uani . . . . . .
H52 H 0.4594 1.0246 0.4371 0.0343 1.0000 Uiso R . . . . .
H51 H 0.4291 0.8371 0.4705 0.0346 1.0000 Uiso R . . . . .
C6 C 0.33557(11) 0.9668(3) 0.39093(10) 0.0285 1.0000 Uani . . . . . .
H62 H 0.3146 1.0441 0.4243 0.0347 1.0000 Uiso R . . . . .
H61 H 0.3320 1.0496 0.3480 0.0346 1.0000 Uiso R . . . . .
C7 C 0.54510(11) 0.7514(3) 0.40601(9) 0.0259 1.0000 Uani . . . . . .
C8 C 0.60281(11) 0.8965(3) 0.40273(9) 0.0267 1.0000 Uani . . . . . .
C9 C 0.68878(11) 0.8692(3) 0.43331(9) 0.0294 1.0000 Uani . . . . . .
C10 C 0.71928(12) 0.6968(3) 0.46654(10) 0.0345 1.0000 Uani . . . . . .
H101 H 0.7771 0.6832 0.4879 0.0409 1.0000 Uiso R . . . . .
C11 C 0.66363(12) 0.5514(3) 0.46779(11) 0.0385 1.0000 Uani . . . . . .
H111 H 0.6837 0.4341 0.4882 0.0457 1.0000 Uiso R . . . . .
C12 C 0.57782(12) 0.5786(3) 0.43822(10) 0.0333 1.0000 Uani . . . . . .
H121 H 0.5408 0.4790 0.4398 0.0383 1.0000 Uiso R . . . . .
C13 C 0.19492(11) 0.8590(3) 0.34132(10) 0.0288 1.0000 Uani . . . . . .
H131 H 0.1899 0.9529 0.3027 0.0347 1.0000 Uiso R . . . . .
H132 H 0.1779 0.9255 0.3793 0.0343 1.0000 Uiso R . . . . .
C14 C 0.13303(11) 0.6985(3) 0.31136(9) 0.0281 1.0000 Uani . . . . . .
H141 H 0.1446 0.6473 0.2677 0.0342 1.0000 Uiso R . . . . .
H142 H 0.0762 0.7540 0.2954 0.0329 1.0000 Uiso R . . . . .
C15 C 0.13412(11) 0.5353(3) 0.36396(9) 0.0283 1.0000 Uani . . . . . .
H151 H 0.1896 0.4738 0.3771 0.0342 1.0000 Uiso R . . . . .
H152 H 0.1224 0.5864 0.4063 0.0361 1.0000 Uiso R . . . . .
C16 C 0.06773(11) 0.3915(3) 0.32777(10) 0.0277 1.0000 Uani . . . . . .
H162 H 0.0139 0.4569 0.3129 0.0335 1.0000 Uiso R . . . . .
H161 H 0.0797 0.3391 0.2854 0.0334 1.0000 Uiso R . . . . .
C18 C 0.00620(11) 0.0996(2) 0.35131(9) 0.0247 1.0000 Uani . . . . . .
C19 C 0.00309(11) -0.0451(3) 0.39950(9) 0.0251 1.0000 Uani . . . . . .
H191 H 0.0403 -0.0443 0.4463 0.0303 1.0000 Uiso R . . . . .
C20 C -0.05395(11) -0.1930(3) 0.37843(9) 0.0268 1.0000 Uani . . . . . .
C21 C -0.11046(12) -0.1994(3) 0.30924(10) 0.0353 1.0000 Uani . . . . . .
C22 C -0.10506(11) -0.0552(3) 0.26203(10) 0.0305 1.0000 Uani . . . . . .
H221 H -0.1406 -0.0590 0.2149 0.0377 1.0000 Uiso R . . . . .
C23 C -0.04754(11) 0.0940(3) 0.28166(9) 0.0270 1.0000 Uani . . . . . .
H231 H -0.0452 0.1909 0.2484 0.0325 1.0000 Uiso R . . . . .
C25 C -0.10500(11) -0.4968(3) 0.41347(9) 0.0273 1.0000 Uani . . . . . .
C270 C -0.1588(4) -0.3901(9) 0.2828(3) 0.0279 0.500(11) Uani . . P 1 1 .
C271 C -0.1874(4) -0.3281(9) 0.2988(3) 0.0295 0.500(11) Uani . . P 1 2 .
H2711 H -0.2303 -0.2619 0.3136 0.0340 0.500(11) Uiso R . P 1 2 .
H2712 H -0.2079 -0.3596 0.2479 0.0336 0.500(11) Uiso R . P 1 2 .
H2701 H -0.2122 -0.3564 0.2489 0.0346 0.500(11) Uiso R . P 1 1 .
H2702 H -0.1273 -0.4729 0.2602 0.0355 0.500(11) Uiso R . P 1 1 .
C260 C -0.1790(3) -0.4819(8) 0.3477(3) 0.0276(12) 0.500(11) Uiso . . P 1 1 .
C261 C -0.1614(4) -0.5165(8) 0.3381(3) 0.0282(12) 0.500(11) Uiso . . P 1 2 .
H2611 H -0.2117 -0.5834 0.3400 0.0340 0.500(11) Uiso . . P 1 2 .
H2612 H -0.1337 -0.5944 0.3116 0.0340 0.500(11) Uiso . . P 1 2 .
H2601 H -0.2221 -0.4082 0.3587 0.0332 0.500(11) Uiso . . P 1 1 .
H2602 H -0.2009 -0.6096 0.3344 0.0332 0.500(11) Uiso . . P 1 1 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.001(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 . C8 . 1.7282(18) yes
Cl2 . C9 . 1.7321(18) yes
O17 . C16 . 1.431(2) yes
O17 . C18 . 1.369(2) yes
O28 . C25 . 1.227(2) yes
N1 . C2 . 1.459(2) yes
N1 . C6 . 1.455(2) yes
N1 . C13 . 1.460(2) yes
N4 . C3 . 1.461(2) yes
N4 . C5 . 1.471(2) yes
N4 . C7 . 1.421(2) yes
N24 . H241 . 0.862 no
N24 . C20 . 1.407(2) yes
N24 . C25 . 1.343(2) yes
C2 . H22 . 0.983 no
C2 . H21 . 0.979 no
C2 . C3 . 1.514(3) yes
C3 . H32 . 0.994 no
C3 . H31 . 0.956 no
C5 . H52 . 0.962 no
C5 . H51 . 0.997 no
C5 . C6 . 1.504(2) yes
C6 . H62 . 0.982 no
C6 . H61 . 1.002 no
C7 . C8 . 1.406(2) yes
C7 . C12 . 1.390(3) yes
C8 . C9 . 1.391(3) yes
C9 . C10 . 1.386(3) yes
C10 . H101 . 0.933 no
C10 . C11 . 1.375(3) yes
C11 . H111 . 0.926 no
C11 . C12 . 1.385(3) yes
C12 . H121 . 0.933 no
C13 . H131 . 0.981 no
C13 . H132 . 0.980 no
C13 . C14 . 1.514(2) yes
C14 . H141 . 0.991 no
C14 . H142 . 0.982 no
C14 . C15 . 1.525(2) yes
C15 . H151 . 0.980 no
C15 . H152 . 0.969 no
C15 . C16 . 1.503(2) yes
C16 . H162 . 0.968 no
C16 . H161 . 0.974 no
C18 . C19 . 1.387(2) yes
C18 . C23 . 1.389(2) yes
C19 . H191 . 0.940 no
C19 . C20 . 1.377(2) yes
C20 . C21 . 1.399(2) yes
C21 . C22 . 1.381(3) yes
C21 . C270 . 1.558(5) yes
C21 . C22 . 1.381(3) yes
C21 . C271 . 1.525(5) yes
C22 . H221 . 0.935 no
C22 . C23 . 1.386(2) yes
C23 . H231 . 0.943 no
C25 . C260 . 1.498(5) yes
C25 . C261 . 1.499(5) yes
C270 . H2701 . 0.966 no
C270 . H2702 . 0.966 no
C270 . C260 . 1.537(8) yes
C271 . H2711 . 0.961 no
C271 . H2712 . 0.973 no
C271 . C261 . 1.515(8) yes
C260 . H2601 . 0.954 no
C260 . H2602 . 0.966 no
C261 . H2611 . 0.966 no
C261 . H2612 . 0.954 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C16 . O17 . C18 . 116.10(13) yes
C2 . N1 . C6 . 108.51(13) yes
C2 . N1 . C13 . 114.00(14) yes
C6 . N1 . C13 . 109.00(14) yes
C3 . N4 . C5 . 109.48(13) yes
C3 . N4 . C7 . 116.33(14) yes
C5 . N4 . C7 . 111.82(13) yes
H241 . N24 . C20 . 117.0 no
H241 . N24 . C25 . 117.1 no
C20 . N24 . C25 . 125.67(15) yes
N1 . C2 . H22 . 111.0 no
N1 . C2 . H21 . 109.5 no
H22 . C2 . H21 . 106.2 no
N1 . C2 . C3 . 110.36(14) yes
H22 . C2 . C3 . 110.9 no
H21 . C2 . C3 . 108.7 no
C2 . C3 . N4 . 109.88(15) yes
C2 . C3 . H32 . 108.3 no
N4 . C3 . H32 . 112.8 no
C2 . C3 . H31 . 110.9 no
N4 . C3 . H31 . 108.4 no
H32 . C3 . H31 . 106.5 no
N4 . C5 . H52 . 109.4 no
N4 . C5 . H51 . 109.0 no
H52 . C5 . H51 . 109.8 no
N4 . C5 . C6 . 111.16(14) yes
H52 . C5 . C6 . 108.8 no
H51 . C5 . C6 . 108.7 no
C5 . C6 . N1 . 110.87(15) yes
C5 . C6 . H62 . 110.2 no
N1 . C6 . H62 . 108.6 no
C5 . C6 . H61 . 109.5 no
N1 . C6 . H61 . 110.7 no
H62 . C6 . H61 . 106.9 no
N4 . C7 . C8 . 119.19(16) yes
N4 . C7 . C12 . 123.52(16) yes
C8 . C7 . C12 . 117.29(16) yes
Cl1 . C8 . C7 . 119.35(14) yes
Cl1 . C8 . C9 . 119.88(14) yes
C7 . C8 . C9 . 120.75(16) yes
Cl2 . C9 . C8 . 121.15(14) yes
Cl2 . C9 . C10 . 118.34(14) yes
C8 . C9 . C10 . 120.50(17) yes
C9 . C10 . H101 . 118.9 no
C9 . C10 . C11 . 119.22(18) yes
H101 . C10 . C11 . 121.8 no
C10 . C11 . H111 . 119.7 no
C10 . C11 . C12 . 120.52(18) yes
H111 . C11 . C12 . 119.8 no
C7 . C12 . C11 . 121.64(18) yes
C7 . C12 . H121 . 118.8 no
C11 . C12 . H121 . 119.6 no
N1 . C13 . H131 . 110.2 no
N1 . C13 . H132 . 108.5 no
H131 . C13 . H132 . 106.6 no
N1 . C13 . C14 . 114.85(15) yes
H131 . C13 . C14 . 107.4 no
H132 . C13 . C14 . 108.9 no
C13 . C14 . H141 . 108.4 no
C13 . C14 . H142 . 108.3 no
H141 . C14 . H142 . 106.2 no
C13 . C14 . C15 . 114.62(15) yes
H141 . C14 . C15 . 110.0 no
H142 . C14 . C15 . 109.0 no
C14 . C15 . H151 . 109.0 no
C14 . C15 . H152 . 109.4 no
H151 . C15 . H152 . 110.2 no
C14 . C15 . C16 . 108.50(14) yes
H151 . C15 . C16 . 109.8 no
H152 . C15 . C16 . 109.9 no
C15 . C16 . O17 . 109.73(14) yes
C15 . C16 . H162 . 108.4 no
O17 . C16 . H162 . 109.5 no
C15 . C16 . H161 . 110.0 no
O17 . C16 . H161 . 110.4 no
H162 . C16 . H161 . 108.8 no
O17 . C18 . C19 . 115.82(15) yes
O17 . C18 . C23 . 124.23(16) yes
C19 . C18 . C23 . 119.95(16) yes
C18 . C19 . H191 . 120.5 no
C18 . C19 . C20 . 119.92(16) yes
H191 . C19 . C20 . 119.6 no
N24 . C20 . C19 . 119.23(15) yes
N24 . C20 . C21 . 119.41(16) yes
C19 . C20 . C21 . 121.35(16) yes
C20 . C21 . C22 . 117.49(17) yes
C20 . C21 . C270 . 118.8(2) yes
C22 . C21 . C270 . 121.7(2) yes
C20 . C21 . C22 . 117.49(17) yes
C20 . C21 . C271 . 116.6(2) yes
C22 . C21 . C271 . 123.5(2) yes
C21 . C22 . H221 . 119.2 no
C21 . C22 . C23 . 122.26(17) yes
H221 . C22 . C23 . 118.5 no
C18 . C23 . C22 . 119.00(16) yes
C18 . C23 . H231 . 120.4 no
C22 . C23 . H231 . 120.6 no
N24 . C25 . O28 . 121.97(16) yes
N24 . C25 . C260 . 115.1(2) yes
O28 . C25 . C260 . 122.1(2) yes
N24 . C25 . O28 . 121.97(16) yes
N24 . C25 . C261 . 116.3(2) yes
O28 . C25 . C261 . 121.0(2) yes
C21 . C270 . H2701 . 107.5 no
C21 . C270 . H2702 . 111.2 no
H2701 . C270 . H2702 . 110.2 no
C21 . C270 . C260 . 107.3(4) yes
H2701 . C270 . C260 . 106.6 no
H2702 . C270 . C260 . 113.8 no
C21 . C271 . H2711 . 110.2 no
C21 . C271 . H2712 . 107.4 no
H2711 . C271 . H2712 . 110.0 no
C21 . C271 . C261 . 109.6(4) yes
H2711 . C271 . C261 . 112.9 no
H2712 . C271 . C261 . 106.4 no
C270 . C260 . C25 . 114.2(4) yes
C270 . C260 . H2601 . 108.6 no
C25 . C260 . H2601 . 109.1 no
C270 . C260 . H2602 . 108.5 no
C25 . C260 . H2602 . 108.4 no
H2601 . C260 . H2602 . 107.8 no
C271 . C261 . C25 . 114.9(4) yes
C271 . C261 . H2611 . 108.3 no
C25 . C261 . H2611 . 107.9 no
C271 . C261 . H2612 . 109.2 no
C25 . C261 . H2612 . 108.6 no
H2611 . C261 . H2612 . 107.8 no


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 20/09/13 at 10:47:50
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT CL   (    1 ,X'S,U'S)  UNTIL N    (   24 ) 
CONT C    (    2 ,X'S,U'S) 
CONT C    (    3 ,X'S,U'S) 
CONT C    (    5 ,X'S,U'S) 
CONT C    (    6 ,X'S,U'S) 
CONT C    (    7 ,X'S,U'S)  UNTIL C    (   10 ) 
CONT C    (   11 ,X'S,U'S) 
CONT C    (   12 ,X'S,U'S) 
CONT C    (   13 ,X'S,U'S) 
CONT C    (   14 ,X'S,U'S) 
CONT C    (   15 ,X'S,U'S) 
CONT C    (   16 ,X'S,U'S) 
CONT C    (   18 ,X'S,U'S)  UNTIL C    (   19 ) 
CONT C    (   20 ,X'S,U'S)  UNTIL C    (   22 ) 
CONT C    (   23 ,X'S,U'S) 
CONT C    (   25 ,X'S,U'S)  UNTIL C    (  271 ) 
CONT C    (  260 ,X'S,U[ISO])  UNTIL C    (  261 ) 
EQUIVALENCE PART(1001, OCC) 
CONTINUE    PART(1002, OCC) 
WEIGHT -1   PART(1002, OCC) 
RIDE N   (  24,X'S) H   ( 241,X'S) 
RIDE C   (   2,X'S) H   (  22,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  32,X'S) H   (  31,X'S) 
RIDE C   (   5,X'S) H   (  52,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  62,X'S) H   (  61,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) H   ( 142,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) 
RIDE C   (  16,X'S) H   ( 162,X'S) H   ( 161,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   ( 270,X'S) H   (2701,X'S) H   (2702,X'S) 
RIDE C   ( 271,X'S) H   (2711,X'S) H   (2712,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 20/09/13 at 10:47:50
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_chemical_name_common            
'aripiprazole; 7-(4-(4-(2,3-dichlorophenyl)-1-piperazinyl)butoxy)-3,4-dihydrocarbostyril'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1-propanol'
####################################################################### 
# 
# 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_alxs0102
_database_code_depnum_ccdc_archive 'CCDC 1422249'
_audit_update_record             
;
2015-09-03 deposited with the CCDC.
2016-01-13 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
'7-(4-(4-(2,3-dichlorophenyl)-1-piperazinyl)butoxy)-3,4-dihydroquinolin-2(1H)-one 1-propanol solvate'

_chemical_name_common            
'aripiprazole 1-propanol solvate; 7-(4-(4-(2,3-dichlorophenyl)-1-piperazinyl)butoxy)-3,4-dihydrocarbostyril 1-propanol solvate'

_chemical_formula_moiety         'C23 H27 Cl N3 O2 0.5(C3 H8 O)'

_chemical_formula_sum            'C24.50 H30.50 Cl2 N3 O2.50'

_chemical_melting_point          ?



_exptl_crystal_description       plate

_exptl_crystal_colour            colourless



_diffrn_ambient_temperature      173(2)

_chemical_formula_weight         477.92



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           triclinic

_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?


loop_

_symmetry_equiv_pos_as_xyz


'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7282(6)

_cell_length_b                   10.7005(8)

_cell_length_c                   15.4954(12)

_cell_angle_alpha                83.8630(10)

_cell_angle_beta                 78.1910(10)

_cell_angle_gamma                73.5760(10)

_cell_volume                     1201.46(16)

_cell_formula_units_Z            2

_cell_measurement_temperature    173(2)

_cell_measurement_reflns_used    6292

_cell_measurement_theta_min      2.34

_cell_measurement_theta_max      25.14

_exptl_crystal_size_max          0.36

_exptl_crystal_size_mid          0.22

_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.321

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             505

_exptl_absorpt_coefficient_mu    0.299

_exptl_absorpt_correction_type   Multi-scan

_exptl_absorpt_correction_T_min  0.9000

_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_process_details   SADABS
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a glass fiber or nylon loop
using Paratone oil for Mo radiation and Mineral oil for Copper radiation.  Data 
were measured using omega and Phi scans of 0.5° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83 to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections. Data reduction was performed using the SAINT software which
corrects for Lp and decay. Scaling and absorption corrections were performed 
by the SADABS program.  The structures are solved by the direct method
using the SHELX-90 program and refined by least squares method on F2 SHELXL-93,
incorporated in SHELXTL V6.1.
 
All H atoms were placed in calculated positions and refined using a riding
model.
C-H(aromatic) = 0.94  Å and Uiso(H) = 1.2Ueq(C)
C-H (alaphatic) = 0.99 Å and Uiso(H) = 1.2Ueq(C)
CH2 = 0.98 Å and Uiso(H) = 1.2Ueq(C)
CH3 = 0.97Å and Uiso(H) = 1.5Ueq(C)
N-H = 0.86 (0.92)Å and Uiso(H) = 1.2 Ueq(N)
O-H(alcohol) = 0.85Åand Uiso(H) = 1.2Ueq(O)
O-H(acid) = 0.82Å and Uiso(H) = 1.5Ueq(O)
;
_diffrn_radiation_probe          x-ray

_diffrn_radiation_type           MoK\a

_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω,and/f 0.5 deg'
_diffrn_detector_area_resol_mean 836.6

_diffrn_standards_number         0

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            15967

_diffrn_reflns_av_R_equivalents  0.0359

_diffrn_reflns_av_sigmaI/netI    0.0348

_diffrn_reflns_limit_h_min       -9

_diffrn_reflns_limit_h_max       9

_diffrn_reflns_limit_k_min       -12

_diffrn_reflns_limit_k_max       12

_diffrn_reflns_limit_l_min       -18

_diffrn_reflns_limit_l_max       18

_diffrn_reflns_theta_min         1.99

_diffrn_reflns_theta_max         25.18

_reflns_number_total             4306

_reflns_number_gt                3185

_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_cell_refinement       'APEX2 (BRUKER, V2010.11-3, 2010)'
_computing_data_reduction        'SAINT (BRUKER, V7.68A, 2010)'
_computing_structure_solution    
'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_refinement  
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'



_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)+(0.0474P)²+0.4800P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         4306

_refine_ls_number_parameters     287

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0611

_refine_ls_R_factor_gt           0.0411

_refine_ls_wR_factor_ref         0.1099

_refine_ls_wR_factor_gt          0.0972

_refine_ls_goodness_of_fit_ref   1.034

_refine_ls_restrained_S_all      1.034

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group


Cl1 Cl -0.24693(8) -0.10727(6) 0.39535(5) 0.0524(2) Uani 1 1 d . . .
Cl2 Cl -0.23760(7) 0.17440(6) 0.32027(4) 0.04507(19) Uani 1 1 d . . .
O17 O 0.4904(2) 0.95341(14) 0.12205(10) 0.0400(4) Uani 1 1 d . . .
O28 O 0.6899(2) 1.55112(14) 0.02114(10) 0.0392(4) Uani 1 1 d . . .
N1 N 0.1882(2) 0.49004(16) 0.28705(11) 0.0303(4) Uani 1 1 d . . .
N4 N 0.1193(2) 0.23720(16) 0.31288(11) 0.0291(4) Uani 1 1 d . . .
N24 N 0.6582(2) 1.34650(16) 0.03346(11) 0.0295(4) Uani 1 1 d . . .
H24A H 0.5659 1.3722 0.0048 0.035 Uiso 1 1 calc R . .
C2 C 0.0045(3) 0.4740(2) 0.32116(15) 0.0347(5) Uani 1 1 d . . .
H2A H -0.0606 0.4802 0.2715 0.042 Uiso 1 1 calc R . .
H2B H -0.0658 0.5450 0.3608 0.042 Uiso 1 1 calc R . .
C3 C 0.0141(3) 0.3436(2) 0.37126(14) 0.0328(5) Uani 1 1 d . . .
H3A H 0.0740 0.3388 0.4227 0.039 Uiso 1 1 calc R . .
H3B H -0.1115 0.3344 0.3934 0.039 Uiso 1 1 calc R . .
C5 C 0.3031(3) 0.2529(2) 0.28104(15) 0.0325(5) Uani 1 1 d . . .
H5A H 0.3757 0.1814 0.2422 0.039 Uiso 1 1 calc R . .
H5B H 0.3651 0.2479 0.3317 0.039 Uiso 1 1 calc R . .
C6 C 0.2937(3) 0.3825(2) 0.23055(15) 0.0336(5) Uani 1 1 d . . .
H6A H 0.4194 0.3915 0.2087 0.040 Uiso 1 1 calc R . .
H6B H 0.2350 0.3862 0.1789 0.040 Uiso 1 1 calc R . .
C7 C 0.1130(3) 0.11087(19) 0.34836(13) 0.0287(5) Uani 1 1 d . . .
C8 C -0.0465(3) 0.0701(2) 0.35480(14) 0.0306(5) Uani 1 1 d . . .
C9 C -0.0513(3) -0.0555(2) 0.38798(14) 0.0338(5) Uani 1 1 d . . .
C10 C 0.1000(3) -0.1420(2) 0.41449(15) 0.0378(5) Uani 1 1 d . . .
H10 H 0.0958 -0.2273 0.4373 0.045 Uiso 1 1 calc R . .
C11 C 0.2569(3) -0.1028(2) 0.40739(15) 0.0385(5) Uani 1 1 d . . .
H11 H 0.3625 -0.1620 0.4249 0.046 Uiso 1 1 calc R . .
C12 C 0.2632(3) 0.0210(2) 0.37527(14) 0.0344(5) Uani 1 1 d . . .
H12 H 0.3735 0.0457 0.3714 0.041 Uiso 1 1 calc R . .
C13 C 0.1796(3) 0.6170(2) 0.23976(15) 0.0343(5) Uani 1 1 d . . .
H13A H 0.0851 0.6851 0.2748 0.041 Uiso 1 1 calc R . .
H13B H 0.1411 0.6162 0.1827 0.041 Uiso 1 1 calc R . .
C14 C 0.3614(3) 0.6523(2) 0.22224(16) 0.0380(5) Uani 1 1 d . . .
H14A H 0.4049 0.6468 0.2787 0.046 Uiso 1 1 calc R . .
H14B H 0.4537 0.5884 0.1831 0.046 Uiso 1 1 calc R . .
C15 C 0.3443(3) 0.7883(2) 0.17964(15) 0.0359(5) Uani 1 1 d . . .
H15A H 0.3024 0.7932 0.1228 0.043 Uiso 1 1 calc R . .
H15B H 0.2504 0.8518 0.2184 0.043 Uiso 1 1 calc R . .
C16 C 0.5230(3) 0.8250(2) 0.16326(15) 0.0383(6) Uani 1 1 d . . .
H16A H 0.5649 0.8237 0.2197 0.046 Uiso 1 1 calc R . .
H16B H 0.6187 0.7627 0.1243 0.046 Uiso 1 1 calc R . .
C18 C 0.6281(3) 1.0144(2) 0.10864(14) 0.0322(5) Uani 1 1 d . . .
C19 C 0.5819(3) 1.1421(2) 0.07583(13) 0.0293(5) Uani 1 1 d . . .
H19A H 0.4640 1.1800 0.0611 0.035 Uiso 1 1 calc R . .
C20 C 0.7079(3) 1.21477(19) 0.06448(13) 0.0276(5) Uani 1 1 d . . .
C21 C 0.8831(3) 1.1614(2) 0.08325(15) 0.0368(5) Uani 1 1 d . . .
C22 C 0.9263(3) 1.0331(2) 0.11417(17) 0.0473(6) Uani 1 1 d . . .
H22A H 1.0459 0.9941 0.1266 0.057 Uiso 1 1 calc R . .
C23 C 0.8014(3) 0.9582(2) 0.12794(16) 0.0430(6) Uani 1 1 d . . .
H23A H 0.8344 0.8701 0.1502 0.052 Uiso 1 1 calc R . .
C25 C 0.7438(3) 1.4354(2) 0.04521(14) 0.0303(5) Uani 1 1 d . . .
C26 C 0.9035(3) 1.3856(2) 0.09166(16) 0.0391(6) Uani 1 1 d . . .
H26A H 0.8584 1.3892 0.1562 0.047 Uiso 1 1 calc R . .
H26B H 0.9863 1.4434 0.0748 0.047 Uiso 1 1 calc R . .
C27 C 1.0112(3) 1.2469(2) 0.07017(18) 0.0476(6) Uani 1 1 d . . .
H27A H 1.0771 1.2453 0.0082 0.057 Uiso 1 1 calc R . .
H27B H 1.1031 1.2138 0.1090 0.057 Uiso 1 1 calc R . .
O1S O 0.2755(4) 0.5255(3) 0.4521(2) 0.0487(8) Uiso 0.50 1 d P . .
H1SA H 0.2181 0.4936 0.4226 0.073 Uiso 0.50 1 d PR . .
C3S C 0.5094(8) 0.4631(6) 0.5382(3) 0.0566(14) Uiso 0.50 1 d P . .
H3SA H 0.6137 0.4063 0.5598 0.068 Uiso 0.50 1 d PR . .
H3SB H 0.4616 0.5498 0.5589 0.068 Uiso 0.50 1 d PR . .
C2SA C 0.4150(10) 0.4176(7) 0.4934(5) 0.060(2) Uiso 0.50 1 d P . .
H2SA H 0.4992 0.3683 0.4466 0.071 Uiso 0.50 1 d PR . .
H2SB H 0.3530 0.3601 0.5308 0.071 Uiso 0.50 1 d PR . .
C2SB C 0.4336(8) 0.4271(6) 0.4639(4) 0.0426(16) Uiso 0.50 1 d P . .
H2SC H 0.5239 0.4233 0.4108 0.051 Uiso 0.50 1 d PR . .
H2SD H 0.4096 0.3432 0.4769 0.051 Uiso 0.50 1 d PR . .






_geom_special_details            
;

 All esds (except the esd in the dihedral angle between two l.s. planes)

 are estimated using the full covariance matrix.  The cell esds are taken

 into account individually in the estimation of esds in distances, angles

 and torsion angles; correlations between esds in cell parameters are only

 used when they are defined by crystal symmetry.  An approximate (isotropic)

 treatment of cell esds is used for estimating esds involving l.s. planes.

;



loop_

_geom_bond_atom_site_label_1

_geom_bond_atom_site_label_2

_geom_bond_distance

_geom_bond_site_symmetry_2

_geom_bond_publ_flag


Cl1 C9 1.731(2) . ?
Cl2 C8 1.725(2) . ?
O17 C18 1.369(2) . ?
O17 C16 1.429(2) . ?
O28 C25 1.232(2) . ?
N1 C2 1.461(2) . ?
N1 C13 1.464(3) . ?
N1 C6 1.466(3) . ?
N4 C7 1.414(3) . ?
N4 C5 1.456(2) . ?
N4 C3 1.474(3) . ?
N24 C25 1.349(3) . ?
N24 C20 1.411(3) . ?
N24 H24A 0.8800 . ?
C2 C3 1.512(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 C6 1.508(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.388(3) . ?
C7 C8 1.401(3) . ?
C8 C9 1.394(3) . ?
C9 C10 1.377(3) . ?
C10 C11 1.371(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.375(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.520(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.515(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.506(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C18 C19 1.380(3) . ?
C18 C23 1.384(3) . ?
C19 C20 1.383(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.390(3) . ?
C21 C22 1.376(3) . ?
C21 C27 1.500(3) . ?
C22 C23 1.391(3) . ?
C22 H22A 0.9500 . ?
C23 H23A 0.9500 . ?
C25 C26 1.495(3) . ?
C26 C27 1.517(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
O1S C2SB 1.399(7) . ?
O1S C2SA 1.524(8) . ?
O1S H1SA 0.8501 . ?
C3S C2SA 1.316(8) . ?
C3S C2SB 1.521(8) . ?
C3S H3SA 0.9599 . ?
C3S H3SB 0.9600 . ?
C2SA H2SA 0.9601 . ?
C2SA H2SB 0.9600 . ?
C2SA H2SD 0.8763 . ?
C2SB H2SA 0.7246 . ?
C2SB H2SC 0.9601 . ?
C2SB H2SD 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

C18 O17 C16 118.19(17) . . ?
C2 N1 C13 111.15(16) . . ?
C2 N1 C6 109.24(16) . . ?
C13 N1 C6 111.58(16) . . ?
C7 N4 C5 114.88(16) . . ?
C7 N4 C3 114.75(16) . . ?
C5 N4 C3 108.74(15) . . ?
C25 N24 C20 123.82(18) . . ?
C25 N24 H24A 118.1 . . ?
C20 N24 H24A 118.1 . . ?
N1 C2 C3 110.96(17) . . ?
N1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N4 C3 C2 109.88(17) . . ?
N4 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
N4 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
N4 C5 C6 110.29(17) . . ?
N4 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
N4 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
N1 C6 C5 110.61(17) . . ?
N1 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C12 C7 C8 117.18(19) . . ?
C12 C7 N4 122.42(18) . . ?
C8 C7 N4 120.37(18) . . ?
C9 C8 C7 120.35(19) . . ?
C9 C8 Cl2 119.49(16) . . ?
C7 C8 Cl2 120.15(16) . . ?
C10 C9 C8 120.96(19) . . ?
C10 C9 Cl1 118.31(17) . . ?
C8 C9 Cl1 120.72(17) . . ?
C11 C10 C9 118.8(2) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C12 120.9(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C7 121.8(2) . . ?
C11 C12 H12 119.1 . . ?
C7 C12 H12 119.1 . . ?
N1 C13 C14 113.13(17) . . ?
N1 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
N1 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C13 111.83(18) . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 112.26(18) . . ?
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 . . ?
O17 C16 C15 107.03(18) . . ?
O17 C16 H16A 110.3 . . ?
C15 C16 H16A 110.3 . . ?
O17 C16 H16B 110.3 . . ?
C15 C16 H16B 110.3 . . ?
H16A C16 H16B 108.6 . . ?
O17 C18 C19 115.12(19) . . ?
O17 C18 C23 124.74(19) . . ?
C19 C18 C23 120.1(2) . . ?
C18 C19 C20 119.7(2) . . ?
C18 C19 H19A 120.1 . . ?
C20 C19 H19A 120.1 . . ?
C19 C20 C21 121.61(19) . . ?
C19 C20 N24 119.53(18) . . ?
C21 C20 N24 118.86(18) . . ?
C22 C21 C20 117.3(2) . . ?
C22 C21 C27 124.2(2) . . ?
C20 C21 C27 118.44(19) . . ?
C21 C22 C23 122.4(2) . . ?
C21 C22 H22A 118.8 . . ?
C23 C22 H22A 118.8 . . ?
C18 C23 C22 118.8(2) . . ?
C18 C23 H23A 120.6 . . ?
C22 C23 H23A 120.6 . . ?
O28 C25 N24 121.71(19) . . ?
O28 C25 C26 122.40(18) . . ?
N24 C25 C26 115.86(18) . . ?
C25 C26 C27 112.80(19) . . ?
C25 C26 H26A 109.0 . . ?
C27 C26 H26A 109.0 . . ?
C25 C26 H26B 109.0 . . ?
C27 C26 H26B 109.0 . . ?
H26A C26 H26B 107.8 . . ?
C21 C27 C26 109.77(19) . . ?
C21 C27 H27A 109.7 . . ?
C26 C27 H27A 109.7 . . ?
C21 C27 H27B 109.7 . . ?
C26 C27 H27B 109.7 . . ?
H27A C27 H27B 108.2 . . ?
C2SB O1S H1SA 106.5 . . ?
C2SA O1S H1SA 110.8 . . ?
C2SB C3S C2SB 124.0(4) 2_666 . ?
C2SA C3S C2SA 123.8(5) . 2_666 ?
C2SB C3S C2SA 109.0(4) . 2_666 ?
C2SA C3S H3SA 120.8 . . ?
C3S C3S H3SA 132.8 2_666 . ?
C2SB C3S H3SA 94.8 2_666 . ?
C2SB C3S H3SA 122.2 . . ?
C2SA C3S H3SA 99.4 2_666 . ?
C2SA C3S H3SB 119.7 . . ?
C2SB C3S H3SB 118.7 . . ?
H3SA C3S H3SB 118.6 . . ?
C3S C2SA O1S 112.8(6) . . ?
C3S C2SA H2SA 108.3 . . ?
O1S C2SA H2SA 108.0 . . ?
C3S C2SA H2SB 110.2 . . ?
O1S C2SA H2SB 109.4 . . ?
H2SA C2SA H2SB 108.0 . . ?
O1S C2SA H2SD 107.3 . . ?
C3S C2SA H2SD 143.2 2_666 . ?
O1S C2SB C3S 108.3(5) . . ?
C3S C2SB H2SA 118.9 2_666 . ?
O1S C2SB H2SA 145.3 . . ?
C3S C2SB H2SA 106.1 . . ?
C3S C2SB H2SB 131.7 2_666 . ?
O1S C2SB H2SC 108.9 . . ?
C3S C2SB H2SC 108.3 . . ?
H2SA C2SB H2SC 54.6 . . ?
O1S C2SB H2SD 112.0 . . ?
C3S C2SB H2SD 110.6 . . ?
H2SC C2SB H2SD 108.7 . . ?



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

C13 N1 C2 C3 -179.05(18) . . . . ?
C6 N1 C2 C3 57.4(2) . . . . ?
C7 N4 C3 C2 -170.57(17) . . . . ?
C5 N4 C3 C2 59.2(2) . . . . ?
N1 C2 C3 N4 -58.9(2) . . . . ?
C7 N4 C5 C6 170.02(17) . . . . ?
C3 N4 C5 C6 -59.8(2) . . . . ?
C2 N1 C6 C5 -57.6(2) . . . . ?
C13 N1 C6 C5 179.14(17) . . . . ?
N4 C5 C6 N1 59.8(2) . . . . ?
C5 N4 C7 C12 18.4(3) . . . . ?
C3 N4 C7 C12 -108.8(2) . . . . ?
C5 N4 C7 C8 -159.38(19) . . . . ?
C3 N4 C7 C8 73.5(2) . . . . ?
C12 C7 C8 C9 0.7(3) . . . . ?
N4 C7 C8 C9 178.58(19) . . . . ?
C12 C7 C8 Cl2 -178.43(16) . . . . ?
N4 C7 C8 Cl2 -0.5(3) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
Cl2 C8 C9 C10 178.72(17) . . . . ?
C7 C8 C9 Cl1 -179.46(16) . . . . ?
Cl2 C8 C9 Cl1 -0.3(3) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
Cl1 C9 C10 C11 178.79(17) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C10 C11 C12 C7 -0.4(3) . . . . ?
C8 C7 C12 C11 -0.3(3) . . . . ?
N4 C7 C12 C11 -178.2(2) . . . . ?
C2 N1 C13 C14 166.17(18) . . . . ?
C6 N1 C13 C14 -71.6(2) . . . . ?
N1 C13 C14 C15 -175.59(18) . . . . ?
C13 C14 C15 C16 179.12(19) . . . . ?
C18 O17 C16 C15 173.36(18) . . . . ?
C14 C15 C16 O17 179.14(18) . . . . ?
C16 O17 C18 C19 -174.49(18) . . . . ?
C16 O17 C18 C23 3.5(3) . . . . ?
O17 C18 C19 C20 176.46(18) . . . . ?
C23 C18 C19 C20 -1.7(3) . . . . ?
C18 C19 C20 C21 1.6(3) . . . . ?
C18 C19 C20 N24 -178.09(18) . . . . ?
C25 N24 C20 C19 158.9(2) . . . . ?
C25 N24 C20 C21 -20.9(3) . . . . ?
C19 C20 C21 C22 -0.3(3) . . . . ?
N24 C20 C21 C22 179.4(2) . . . . ?
C19 C20 C21 C27 -179.3(2) . . . . ?
N24 C20 C21 C27 0.4(3) . . . . ?
C20 C21 C22 C23 -1.0(4) . . . . ?
C27 C21 C22 C23 178.0(2) . . . . ?
O17 C18 C23 C22 -177.5(2) . . . . ?
C19 C18 C23 C22 0.4(3) . . . . ?
C21 C22 C23 C18 0.9(4) . . . . ?
C20 N24 C25 O28 -176.09(19) . . . . ?
C20 N24 C25 C26 2.0(3) . . . . ?
O28 C25 C26 C27 -147.4(2) . . . . ?
N24 C25 C26 C27 34.5(3) . . . . ?
C22 C21 C27 C26 -144.9(2) . . . . ?
C20 C21 C27 C26 34.0(3) . . . . ?
C25 C26 C27 C21 -50.8(3) . . . . ?
C3S C3S C2SA O1S -41.6(7) 2_666 . . . ?
C2SB C3S C2SA O1S -28.4(12) 2_666 . . . ?
C2SB C3S C2SA O1S -70.5(16) . . . . ?
C2SA C3S C2SA O1S -41.6(7) 2_666 . . . ?
O1S C3S C2SA O1S -117.7(8) 2_666 . . . ?
C2SB C3S C2SA C3S 13.2(7) 2_666 . . 2_666 ?
C2SB C3S C2SA C3S -28.9(16) . . . 2_666 ?
C2SA C3S C2SA C3S 0.001(2) 2_666 . . 2_666 ?
O1S C3S C2SA C3S -76.1(9) 2_666 . . 2_666 ?
C2SB O1S C2SA C3S 100.1(17) . . . . ?
C3S O1S C2SA C3S 36.2(6) 2_666 . . . ?
C2SB O1S C2SA C3S 63.9(14) . . . 2_666 ?
C2SA O1S C2SB C3S -103.6(16) . . . 2_666 ?
C2SA O1S C2SB C3S -55.8(14) . . . . ?
C3S O1S C2SB C3S 47.8(5) 2_666 . . . ?
C2SA C3S C2SB C3S 146.7(19) . . . 2_666 ?
C2SB C3S C2SB C3S -0.001(2) 2_666 . . 2_666 ?
C2SA C3S C2SB C3S -8.2(5) 2_666 . . 2_666 ?
O1S C3S C2SB C3S -67.4(6) 2_666 . . 2_666 ?
C2SA C3S C2SB O1S 85.8(17) . . . . ?
C3S C3S C2SB O1S -60.9(6) 2_666 . . . ?
C2SB C3S C2SB O1S -60.9(6) 2_666 . . . ?
C2SA C3S C2SB O1S -69.1(6) 2_666 . . . ?
O1S C3S C2SB O1S -128.3(5) 2_666 . . . ?



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


N24 H24A O28 0.88 2.02 2.867(2) 161.1 2_685
O1S H1SA N1 0.85 2.17 2.863(4) 139.1 .



_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        25.18

_diffrn_measured_fraction_theta_full 0.996

_refine_diff_density_max         0.335

_refine_diff_density_min         -0.330

_refine_diff_density_rms         0.045

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1-propanol'
