# 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. 
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data_BA73M
_database_code_depnum_ccdc_archive 'CCDC 1430980'
_audit_update_record             
;
2015-10-13 deposited with the CCDC.
2016-01-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT420_BA73M               
;
PROBLEM:
PLAT420_ALERT_2_B D-H Without Acceptor >O4 - >H4O .. Please Check
RESPONSE:The hydroxyl acts as donor and participates in a weak intermolecualar
hydrogen bonding with water oxygen acceptor [O4-H4O...O6W:  
D-H, 0.82; H...A, 2.77; D...A, 3.596(9) Ang; D-H...A, 172 Deg]. 
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1:1 cocrystal of Aripiprazole Phloroglucinol Hydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H27 Cl2 N3 O2, C6 H6 O3, O'
_chemical_formula_sum            'C29 H33 Cl2 N3 O6'
_chemical_formula_weight         590.48

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                   14.8405(6)
_cell_length_b                   10.2671(4)
_cell_length_c                   20.6587(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.2190(10)
_cell_angle_gamma                90
_cell_volume                     2953.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8444
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      26.61

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             1240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.266
_shelx_estimated_absorpt_T_min   0.896
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27780
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.101
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5225
_reflns_number_gt                4443
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_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)+(0.1231P)²+2.0698P] 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         5225
_refine_ls_number_parameters     402
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0730
_refine_ls_wR_factor_ref         0.2151
_refine_ls_wR_factor_gt          0.2054
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C -0.0037(2) -0.1672(3) 0.44210(16) 0.0492(7) Uani 1 1 d . . . . .
C2 C -0.0031(3) -0.2906(4) 0.4032(2) 0.0676(10) Uani 1 1 d . . . . .
H2A H -0.0452 -0.3534 0.4132 0.081 Uiso 1 1 calc R U . . .
H2B H -0.0287 -0.2722 0.3541 0.081 Uiso 1 1 calc R U . . .
C3 C 0.0948(3) -0.3500(4) 0.4202(3) 0.0818(13) Uani 1 1 d . . . . .
H3A H 0.0928 -0.4173 0.3868 0.098 Uiso 1 1 calc R U . . .
H3B H 0.1139 -0.3900 0.4654 0.098 Uiso 1 1 calc R U . . .
C4 C 0.1673(3) -0.2479(3) 0.4193(2) 0.0596(9) Uani 1 1 d . . . . .
C5 C 0.15872(19) -0.1249(3) 0.44429(15) 0.0434(7) Uani 1 1 d . . . . .
C6 C 0.22479(19) -0.0281(3) 0.44914(14) 0.0424(6) Uani 1 1 d . . . . .
H6 H 0.2178 0.0534 0.4665 0.051 Uiso 1 1 calc R U . . .
C7 C 0.3020(2) -0.0535(3) 0.42772(16) 0.0486(7) Uani 1 1 d . . . . .
C8 C 0.3112(3) -0.1746(4) 0.4013(2) 0.0634(9) Uani 1 1 d . . . . .
H8 H 0.3622 -0.1916 0.3862 0.076 Uiso 1 1 calc R U . . .
C9 C 0.2444(3) -0.2696(4) 0.3977(2) 0.0720(11) Uani 1 1 d . . . . .
H9 H 0.2512 -0.3509 0.3801 0.086 Uiso 1 1 calc R U . . .
C10 C 0.4381(2) 0.0351(4) 0.40542(18) 0.0569(8) Uani 1 1 d . . . . .
H10A H 0.4112 0.0103 0.3572 0.068 Uiso 1 1 calc R U . . .
H10B H 0.4835 -0.0315 0.4300 0.068 Uiso 1 1 calc R U . . .
C11 C 0.4874(2) 0.1650(4) 0.4126(2) 0.0607(9) Uani 1 1 d . . . . .
H11A H 0.5151 0.1874 0.4611 0.073 Uiso 1 1 calc R U . . .
H11B H 0.4405 0.2312 0.3900 0.073 Uiso 1 1 calc R U . . .
C12 C 0.5660(2) 0.1630(4) 0.3811(2) 0.0588(9) Uani 1 1 d . . . . .
H12A H 0.5378 0.1449 0.3321 0.071 Uiso 1 1 calc R U . . .
H12B H 0.6113 0.0940 0.4021 0.071 Uiso 1 1 calc R U . . .
C13 C 0.6186(3) 0.2927(4) 0.3917(2) 0.0723(11) Uani 1 1 d . . . . .
H13A H 0.5721 0.3629 0.3836 0.087 Uiso 1 1 calc R U . . .
H13B H 0.6614 0.2988 0.4393 0.087 Uiso 1 1 calc R U . . .
C14 C 0.7121(3) 0.4450(3) 0.3510(3) 0.0768(12) Uani 1 1 d . . . . .
H14A H 0.7513 0.4629 0.3985 0.092 Uiso 1 1 calc R U . . .
H14B H 0.6586 0.5056 0.3378 0.092 Uiso 1 1 calc R U . . .
C15 C 0.7715(2) 0.4645(3) 0.3047(2) 0.0624(9) Uani 1 1 d . . . . .
H15A H 0.7327 0.4465 0.2571 0.075 Uiso 1 1 calc R U . . .
H15B H 0.7937 0.5539 0.3077 0.075 Uiso 1 1 calc R U . . .
C16 C 0.7575(2) 0.2208(3) 0.36484(17) 0.0486(7) Uani 1 1 d . . . . .
H16A H 0.7348 0.1315 0.3601 0.058 Uiso 1 1 calc R U . . .
H16B H 0.7964 0.2350 0.4128 0.058 Uiso 1 1 calc R U . . .
C17 C 0.8180(2) 0.2419(3) 0.32028(17) 0.0457(7) Uani 1 1 d . . . . .
H17A H 0.8721 0.1824 0.3341 0.055 Uiso 1 1 calc R U . . .
H17B H 0.7801 0.2241 0.2725 0.055 Uiso 1 1 calc R U . . .
C18 C 0.9270(2) 0.3985(3) 0.29985(15) 0.0432(7) Uani 1 1 d . . . . .
C19 C 1.0182(2) 0.3453(3) 0.33379(15) 0.0438(7) Uani 1 1 d . . . . .
C20 C 1.0914(2) 0.3606(3) 0.30726(17) 0.0507(7) Uani 1 1 d . . . . .
C21 C 1.0786(2) 0.4363(4) 0.25025(19) 0.0621(9) Uani 1 1 d . . . . .
H21 H 1.1286 0.4488 0.2335 0.074 Uiso 1 1 calc R U . . .
C22 C 0.9909(3) 0.4936(4) 0.2182(2) 0.0679(10) Uani 1 1 d . . . . .
H22 H 0.9820 0.5467 0.1800 0.081 Uiso 1 1 calc R U . . .
C23 C 0.9156(2) 0.4734(4) 0.24182(18) 0.0580(8) Uani 1 1 d . . . . .
H23 H 0.8561 0.5109 0.2183 0.070 Uiso 1 1 calc R U . . .
C24 C 0.4744(4) 0.3059(5) 0.2042(3) 0.0492(10) Uani 0.564(2) 1 d D . P A 1
C25 C 0.4461(4) 0.3904(6) 0.2456(3) 0.0563(14) Uani 0.564(2) 1 d D . P A 1
H25 H 0.4915 0.4260 0.2848 0.068 Uiso 0.564(2) 1 calc R U P A 1
C26 C 0.3503(4) 0.4221(6) 0.2288(3) 0.0625(12) Uani 0.564(2) 1 d D . P A 1
C27 C 0.2829(11) 0.364(3) 0.1726(11) 0.076(3) Uani 0.564(2) 1 d D . P A 1
H27 H 0.2178 0.3750 0.1651 0.091 Uiso 0.564(2) 1 calc R U P A 1
C28 C 0.3114(8) 0.289(4) 0.1268(13) 0.0594(16) Uani 0.564(2) 1 d D . P A 1
C29 C 0.4084(4) 0.2561(7) 0.1437(4) 0.0609(15) Uani 0.564(2) 1 d D . P A 1
H29 H 0.4283 0.2022 0.1151 0.073 Uiso 0.564(2) 1 calc R U P A 1
C24D C 0.4901(4) 0.2238(7) 0.1664(3) 0.0492(10) Uani 0.436(2) 1 d D . P A 2
C25D C 0.4611(5) 0.1601(9) 0.1038(3) 0.062(2) Uani 0.436(2) 1 d D . P A 2
H25D H 0.5063 0.1116 0.0922 0.075 Uiso 0.436(2) 1 calc R U P A 2
C26D C 0.3679(5) 0.1647(8) 0.0572(3) 0.0625(12) Uani 0.436(2) 1 d D . P A 2
C27D C 0.3048(7) 0.2397(10) 0.0766(5) 0.0733(12) Uani 0.436(2) 1 d D . P A 2
H27D H 0.2427 0.2496 0.0453 0.088 Uiso 0.436(2) 1 calc R U P A 2
C28D C 0.3279(12) 0.301(5) 0.1395(16) 0.0594(16) Uani 0.436(2) 1 d D . P A 2
C29D C 0.4237(6) 0.2938(9) 0.1851(5) 0.0609(15) Uani 0.436(2) 1 d D . P A 2
H29D H 0.4419 0.3359 0.2275 0.073 Uiso 0.436(2) 1 calc R U P A 2
Cl1 Cl 1.04186(6) 0.26770(9) 0.41244(4) 0.0588(3) Uani 1 1 d . . . . .
Cl2 Cl 1.20217(6) 0.28727(11) 0.34745(6) 0.0814(4) Uani 1 1 d . . . . .
H1N H 0.079(2) -0.028(2) 0.4836(15) 0.048(9) Uiso 1 1 d D . . . .
N1 N 0.07716(17) -0.0980(3) 0.46272(13) 0.0446(6) Uani 1 1 d D . . . .
N2 N 0.67506(19) 0.3095(3) 0.34533(16) 0.0546(7) Uani 1 1 d . . . . .
N3 N 0.85294(17) 0.3765(2) 0.32707(14) 0.0467(6) Uani 1 1 d . . . . .
O1 O -0.07556(15) -0.1305(2) 0.45375(13) 0.0614(6) Uani 1 1 d . . . . .
O2 O 0.36353(15) 0.0488(2) 0.43410(13) 0.0610(6) Uani 1 1 d . . . . .
O3 O 0.5687(4) 0.2707(6) 0.2206(3) 0.0605(12) Uani 0.564(2) 1 d D . P A 1
H3O H 0.6017 0.3066 0.2564 0.091 Uiso 0.564(2) 1 d DR U P A 1
H4O H 0.3527 0.5005 0.3077 0.091 Uiso 0.564(2) 1 d DR U P A 1
H5O H 0.1864 0.2800 0.0580 0.091 Uiso 0.564(2) 1 d DR U P A 1
O4 O 0.3173(4) 0.5041(6) 0.2667(3) 0.0817(12) Uani 0.564(2) 1 d D . P A 1
O5 O 0.2483(3) 0.2363(5) 0.0693(3) 0.0733(12) Uani 0.564(2) 1 d D . P A 1
O3D O 0.5826(5) 0.2125(8) 0.2065(4) 0.0605(12) Uani 0.436(2) 1 d D . P A 2
H3D H 0.5942 0.2519 0.2430 0.091 Uiso 0.436(2) 1 d DR U P A 2
H4D H 0.3893 0.0548 -0.0059 0.091 Uiso 0.436(2) 1 d DR U P A 2
H5D H 0.2148 0.3966 0.1196 0.091 Uiso 0.436(2) 1 d DR U P A 2
O4D O 0.3405(4) 0.0980(7) -0.0037(3) 0.0817(12) Uani 0.436(2) 1 d D . P A 2
O5D O 0.2683(10) 0.378(2) 0.1597(9) 0.076(3) Uani 0.436(2) 1 d D . P A 2
O6D O 0.3807(11) 0.5210(14) 0.3102(9) 0.184(3) Uani 0.436(2) 1 d . . P A 2
O6W O 0.4609(7) 0.5234(11) 0.4467(4) 0.184(3) Uani 0.564(2) 1 d . . P A 1


_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
C1 O1 1.231(4) . ?
C1 N1 1.331(4) . ?
C1 C2 1.502(5) . ?
C2 C3 1.500(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.507(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C9 1.383(5) . ?
C4 C5 1.386(5) . ?
C5 C6 1.375(4) . ?
C5 N1 1.416(3) . ?
C6 C7 1.388(4) . ?
C6 H6 0.9300 . ?
C7 O2 1.368(4) . ?
C7 C8 1.383(5) . ?
C8 C9 1.374(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 O2 1.432(3) . ?
C10 C11 1.503(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.520(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.521(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N2 1.486(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N2 1.485(4) . ?
C14 C15 1.522(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N3 1.451(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N2 1.466(4) . ?
C16 C17 1.507(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N3 1.466(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C23 1.385(4) . ?
C18 C19 1.403(4) . ?
C18 N3 1.415(4) . ?
C19 C20 1.384(4) . ?
C19 Cl1 1.733(3) . ?
C20 C21 1.369(5) . ?
C20 Cl2 1.737(3) . ?
C21 C22 1.372(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.381(5) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 O3 1.370(7) . ?
C24 C25 1.383(7) . ?
C24 C29 1.392(7) . ?
C25 C26 1.381(6) . ?
C25 H25 0.9300 . ?
C26 O4 1.350(4) . ?
C26 C27 1.380(10) . ?
C27 C28 1.397(9) . ?
C27 H27 0.9300 . ?
C28 O5 1.345(5) . ?
C28 C29 1.399(8) . ?
C29 H29 0.9300 . ?
C24D O3D 1.340(9) . ?
C24D C29D 1.379(8) . ?
C24D C25D 1.379(8) . ?
C25D C26D 1.387(7) . ?
C25D H25D 0.9300 . ?
C26D O4D 1.365(5) . ?
C26D C27D 1.374(8) . ?
C27D C28D 1.377(9) . ?
C27D H27D 0.9300 . ?
C28D O5D 1.354(5) . ?
C28D C29D 1.409(9) . ?
C29D H29D 0.9300 . ?
N1 H1N 0.833(18) . ?
O3 H3O 0.8195 . ?
O4 H4O 0.8299 . ?
O5 H5O 0.9762 . ?
O3D H3D 0.8200 . ?
O4D H4D 0.8635 . ?
O5D H5D 0.9475 . ?

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
O1 C1 N1 121.3(3) . . ?
O1 C1 C2 122.0(3) . . ?
N1 C1 C2 116.7(3) . . ?
C3 C2 C1 113.7(3) . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C2 C3 C4 110.6(3) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C9 C4 C5 117.4(3) . . ?
C9 C4 C3 124.5(3) . . ?
C5 C4 C3 118.1(3) . . ?
C6 C5 C4 122.1(3) . . ?
C6 C5 N1 119.6(3) . . ?
C4 C5 N1 118.3(3) . . ?
C5 C6 C7 119.1(3) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
O2 C7 C8 125.1(3) . . ?
O2 C7 C6 114.9(3) . . ?
C8 C7 C6 120.0(3) . . ?
C9 C8 C7 119.5(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C4 122.0(3) . . ?
C8 C9 H9 119.0 . . ?
C4 C9 H9 119.0 . . ?
O2 C10 C11 106.9(3) . . ?
O2 C10 H10A 110.3 . . ?
C11 C10 H10A 110.3 . . ?
O2 C10 H10B 110.3 . . ?
C11 C10 H10B 110.3 . . ?
H10A C10 H10B 108.6 . . ?
C10 C11 C12 111.4(3) . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 111.0(3) . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
N2 C13 C12 112.6(3) . . ?
N2 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
N2 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
N2 C14 C15 110.6(3) . . ?
N2 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N3 C15 C14 108.6(3) . . ?
N3 C15 H15A 110.0 . . ?
C14 C15 H15A 110.0 . . ?
N3 C15 H15B 110.0 . . ?
C14 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?
N2 C16 C17 111.1(3) . . ?
N2 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
N2 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
N3 C17 C16 110.0(2) . . ?
N3 C17 H17A 109.7 . . ?
C16 C17 H17A 109.7 . . ?
N3 C17 H17B 109.7 . . ?
C16 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C23 C18 C19 117.2(3) . . ?
C23 C18 N3 123.6(3) . . ?
C19 C18 N3 119.2(3) . . ?
C20 C19 C18 120.8(3) . . ?
C20 C19 Cl1 119.4(2) . . ?
C18 C19 Cl1 119.7(2) . . ?
C21 C20 C19 120.7(3) . . ?
C21 C20 Cl2 118.9(2) . . ?
C19 C20 Cl2 120.3(3) . . ?
C20 C21 C22 119.0(3) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C21 C22 C23 120.9(3) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C22 C23 C18 121.1(3) . . ?
C22 C23 H23 119.4 . . ?
C18 C23 H23 119.4 . . ?
O3 C24 C25 121.1(5) . . ?
O3 C24 C29 117.9(5) . . ?
C25 C24 C29 121.0(6) . . ?
C26 C25 C24 120.0(5) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
O4 C26 C27 117.1(8) . . ?
O4 C26 C25 123.3(5) . . ?
C27 C26 C25 119.6(8) . . ?
C26 C27 C28 120.6(12) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
O5 C28 C27 122.6(8) . . ?
O5 C28 C29 117.9(7) . . ?
C27 C28 C29 119.3(8) . . ?
C24 C29 C28 118.8(6) . . ?
C24 C29 H29 120.6 . . ?
C28 C29 H29 120.6 . . ?
O3D C24D C29D 123.4(7) . . ?
O3D C24D C25D 117.4(6) . . ?
C29D C24D C25D 119.2(7) . . ?
C24D C25D C26D 123.2(7) . . ?
C24D C25D H25D 118.4 . . ?
C26D C25D H25D 118.4 . . ?
O4D C26D C27D 122.3(7) . . ?
O4D C26D C25D 122.0(6) . . ?
C27D C26D C25D 115.8(7) . . ?
C26D C27D C28D 124.0(9) . . ?
C26D C27D H27D 118.0 . . ?
C28D C27D H27D 118.0 . . ?
O5D C28D C27D 125.5(11) . . ?
O5D C28D C29D 116.2(9) . . ?
C27D C28D C29D 118.1(11) . . ?
C24D C29D C28D 119.7(10) . . ?
C24D C29D H29D 120.2 . . ?
C28D C29D H29D 120.2 . . ?
C1 N1 C5 124.7(3) . . ?
C1 N1 H1N 119(2) . . ?
C5 N1 H1N 116(2) . . ?
C16 N2 C14 108.0(3) . . ?
C16 N2 C13 110.7(3) . . ?
C14 N2 C13 109.5(3) . . ?
C18 N3 C15 116.8(2) . . ?
C18 N3 C17 114.2(2) . . ?
C15 N3 C17 109.2(2) . . ?
C7 O2 C10 118.1(3) . . ?
C24 O3 H3O 110.1 . . ?
C26 O4 H4O 109.6 . . ?
C28 O5 H5O 109.7 . . ?
C24D O3D H3D 111.8 . . ?
C26D O4D H4D 108.6 . . ?
C28D O5D H5D 106.8 . . ?

_refine_diff_density_max         0.851
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_AS51M
_database_code_depnum_ccdc_archive 'CCDC 1430981'
_audit_update_record             
;
2015-10-13 deposited with the CCDC.
2016-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '1:1 cocrystal of Aripiprazole Resorcinol'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H27 Cl2 N3 O2, C6 H6 O2'
_chemical_formula_sum            'C29 H33 Cl2 N3 O4'
_chemical_formula_weight         558.48

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      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                   14.7282(12)
_cell_length_b                   9.8820(8)
_cell_length_c                   20.8815(14)
_cell_angle_alpha                90
_cell_angle_beta                 111.174(5)
_cell_angle_gamma                90
_cell_volume                     2834.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6098
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      28.21

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.268
_shelx_estimated_absorpt_T_min   0.919
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28020
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.082
_diffrn_reflns_theta_max         25.680
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5359
_reflns_number_gt                4616
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_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)+(0.0657P)²+0.4662P] 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         5359
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.1075
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 1.00656(11) -0.17888(17) 0.55526(7) 0.0481(4) Uani 1 1 d . . . . .
C2 C 1.00548(14) -0.31261(19) 0.58899(10) 0.0656(5) Uani 1 1 d . . . . .
H2A H 1.0264 -0.2995 0.6383 0.079 Uiso 1 1 calc R U . . .
H2B H 1.0516 -0.3731 0.5802 0.079 Uiso 1 1 calc R U . . .
C3 C 0.90515(15) -0.37801(18) 0.56319(12) 0.0731(5) Uani 1 1 d . . . . .
H3A H 0.8896 -0.4088 0.5163 0.088 Uiso 1 1 calc R U . . .
H3B H 0.9051 -0.4560 0.5914 0.088 Uiso 1 1 calc R U . . .
C4 C 0.82961(13) -0.27831(16) 0.56587(9) 0.0549(4) Uani 1 1 d . . . . .
C5 C 0.83882(10) -0.14601(14) 0.54685(7) 0.0417(3) Uani 1 1 d . . . . .
C6 C 0.77171(10) -0.04720(15) 0.54508(7) 0.0429(3) Uani 1 1 d . . . . .
H6 H 0.7783 0.0402 0.5308 0.051 Uiso 1 1 calc R U . . .
C7 C 0.69410(10) -0.08034(16) 0.56501(7) 0.0464(3) Uani 1 1 d . . . . .
C8 C 0.68403(13) -0.21090(18) 0.58533(9) 0.0584(4) Uani 1 1 d . . . . .
H8 H 0.6323 -0.2331 0.5989 0.070 Uiso 1 1 calc R U . . .
C9 C 0.75159(14) -0.30819(18) 0.58528(10) 0.0631(5) Uani 1 1 d . . . . .
H9 H 0.7443 -0.3960 0.5987 0.076 Uiso 1 1 calc R U . . .
C10 C 0.56058(11) 0.00432(18) 0.59392(8) 0.0534(4) Uani 1 1 d . . . . .
H10A H 0.5893 -0.0364 0.6390 0.064 Uiso 1 1 calc R U . . .
H10B H 0.5099 -0.0552 0.5651 0.064 Uiso 1 1 calc R U . . .
C11 C 0.51923(11) 0.14016(18) 0.59919(9) 0.0575(4) Uani 1 1 d . . . . .
H11A H 0.4899 0.1786 0.5536 0.069 Uiso 1 1 calc R U . . .
H11B H 0.5715 0.1998 0.6259 0.069 Uiso 1 1 calc R U . . .
C12 C 0.44293(11) 0.13309(17) 0.63265(9) 0.0541(4) Uani 1 1 d . . . . .
H12A H 0.3919 0.0705 0.6073 0.065 Uiso 1 1 calc R U . . .
H12B H 0.4728 0.0996 0.6793 0.065 Uiso 1 1 calc R U . . .
C13 C 0.39921(12) 0.27125(17) 0.63374(9) 0.0553(4) Uani 1 1 d . . . . .
H13A H 0.4516 0.3363 0.6517 0.066 Uiso 1 1 calc R U . . .
H13B H 0.3611 0.2975 0.5869 0.066 Uiso 1 1 calc R U . . .
C14 C 0.30476(12) 0.41902(16) 0.67650(10) 0.0565(4) Uani 1 1 d . . . . .
H14A H 0.2715 0.4501 0.6298 0.068 Uiso 1 1 calc R U . . .
H14B H 0.3615 0.4760 0.6973 0.068 Uiso 1 1 calc R U . . .
C15 C 0.23751(11) 0.43359(16) 0.71610(9) 0.0527(4) Uani 1 1 d . . . . .
H15A H 0.2711 0.4065 0.7635 0.063 Uiso 1 1 calc R U . . .
H15B H 0.2180 0.5274 0.7157 0.063 Uiso 1 1 calc R U . . .
C16 C 0.24967(10) 0.19283(15) 0.64595(8) 0.0452(3) Uani 1 1 d . . . . .
H16A H 0.2694 0.0990 0.6467 0.054 Uiso 1 1 calc R U . . .
H16B H 0.2149 0.2184 0.5985 0.054 Uiso 1 1 calc R U . . .
C17 C 0.18342(10) 0.20732(14) 0.68591(8) 0.0436(3) Uani 1 1 d . . . . .
H17A H 0.1270 0.1494 0.6661 0.052 Uiso 1 1 calc R U . . .
H17B H 0.2174 0.1789 0.7330 0.052 Uiso 1 1 calc R U . . .
C18 C 0.07371(10) 0.36868(14) 0.70802(7) 0.0409(3) Uani 1 1 d . . . . .
C19 C -0.01983(10) 0.32103(14) 0.66845(7) 0.0404(3) Uani 1 1 d . . . . .
C20 C -0.09725(10) 0.33700(16) 0.69057(8) 0.0469(3) Uani 1 1 d . . . . .
C21 C -0.08575(12) 0.40579(18) 0.75039(8) 0.0566(4) Uani 1 1 d . . . . .
H21 H -0.1379 0.4168 0.7651 0.068 Uiso 1 1 calc R U . . .
C22 C 0.00429(13) 0.45774(19) 0.78785(8) 0.0612(4) Uani 1 1 d . . . . .
H22 H 0.0124 0.5068 0.8275 0.073 Uiso 1 1 calc R U . . .
C23 C 0.08294(11) 0.43868(17) 0.76791(8) 0.0530(4) Uani 1 1 d . . . . .
H23 H 0.1434 0.4733 0.7950 0.064 Uiso 1 1 calc R U . . .
C24 C 0.50945(12) 0.17480(18) 0.84492(8) 0.0565(4) Uani 1 1 d . . . . .
C25 C 0.57612(13) 0.24926(17) 0.82733(9) 0.0576(4) Uani 1 1 d . . . . .
H25 H 0.5578 0.2902 0.7844 0.069 Uiso 1 1 calc R U . . .
C26 C 0.67141(13) 0.26302(17) 0.87431(10) 0.0610(4) Uani 1 1 d . . . . .
C27 C 0.69822(15) 0.2054(2) 0.93835(10) 0.0703(5) Uani 1 1 d . . . . .
H27 H 0.7614 0.2154 0.9698 0.084 Uiso 1 1 calc R U . . .
C28 C 0.63081(16) 0.1329(2) 0.95536(10) 0.0749(6) Uani 1 1 d . . . . .
H28 H 0.6488 0.0944 0.9988 0.090 Uiso 1 1 calc R U . . .
C29 C 0.53646(14) 0.1158(2) 0.90933(9) 0.0665(5) Uani 1 1 d . . . . .
H29 H 0.4919 0.0653 0.9215 0.080 Uiso 1 1 calc R U . . .
Cl1 Cl -0.04045(3) 0.25104(4) 0.58841(2) 0.05008(12) Uani 1 1 d . . . . .
Cl2 Cl -0.21130(3) 0.27333(5) 0.64233(3) 0.06826(15) Uani 1 1 d . . . . .
H3O H 0.4042(19) 0.199(3) 0.7664(13) 0.094(8) Uiso 1 1 d . . . . .
H4O H 0.7920(19) 0.341(2) 0.8871(13) 0.097(8) Uiso 1 1 d . . . . .
N1 N 0.92209(9) -0.11123(14) 0.53154(6) 0.0444(3) Uani 1 1 d . . . . .
N2 N 0.33656(9) 0.27845(12) 0.67510(7) 0.0445(3) Uani 1 1 d . . . . .
N3 N 0.15164(8) 0.34888(11) 0.68486(6) 0.0418(3) Uani 1 1 d . . . . .
O1 O 1.08094(7) -0.13157(12) 0.54923(6) 0.0561(3) Uani 1 1 d . . . . .
O2 O 0.63347(8) 0.02503(12) 0.56423(6) 0.0571(3) Uani 1 1 d . . . . .
O3 O 0.41592(9) 0.15641(17) 0.80197(7) 0.0715(4) Uani 1 1 d . . . . .
O4 O 0.73463(11) 0.33454(16) 0.85316(9) 0.0868(5) Uani 1 1 d . . . . .
H1N H 0.9231(11) -0.0416(18) 0.5129(8) 0.047(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.2386(19) . ?
C1 N1 1.3397(19) . ?
C1 C2 1.500(2) . ?
C2 C3 1.522(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.502(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C9 1.381(2) . ?
C4 C5 1.387(2) . ?
C5 C6 1.380(2) . ?
C5 N1 1.4169(18) . ?
C6 C7 1.3894(19) . ?
C6 H6 0.9300 . ?
C7 O2 1.3680(18) . ?
C7 C8 1.383(2) . ?
C8 C9 1.384(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 O2 1.4351(17) . ?
C10 C11 1.494(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.524(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.513(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N2 1.4759(19) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N2 1.470(2) . ?
C14 C15 1.509(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N3 1.4594(18) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N2 1.4702(18) . ?
C16 C17 1.502(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N3 1.4728(18) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C23 1.392(2) . ?
C18 C19 1.407(2) . ?
C18 N3 1.4109(17) . ?
C19 C20 1.385(2) . ?
C19 Cl1 1.7312(14) . ?
C20 C21 1.378(2) . ?
C20 Cl2 1.7349(15) . ?
C21 C22 1.373(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(2) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 O3 1.357(2) . ?
C24 C25 1.379(3) . ?
C24 C29 1.386(3) . ?
C25 C26 1.399(2) . ?
C25 H25 0.9300 . ?
C26 O4 1.363(3) . ?
C26 C27 1.374(3) . ?
C27 C28 1.371(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.385(3) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
N1 H1N 0.794(17) . ?
O3 H3O 0.82(2) . ?
O4 H4O 0.89(3) . ?

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
O1 C1 N1 120.76(15) . . ?
O1 C1 C2 122.68(14) . . ?
N1 C1 C2 116.56(14) . . ?
C1 C2 C3 112.42(14) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C2 110.23(15) . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C9 C4 C5 117.59(15) . . ?
C9 C4 C3 125.21(16) . . ?
C5 C4 C3 117.20(15) . . ?
C6 C5 C4 122.09(13) . . ?
C6 C5 N1 119.49(13) . . ?
C4 C5 N1 118.38(13) . . ?
C5 C6 C7 118.94(14) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
O2 C7 C8 124.89(13) . . ?
O2 C7 C6 114.91(13) . . ?
C8 C7 C6 120.19(14) . . ?
C7 C8 C9 119.42(15) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C4 C9 C8 121.75(16) . . ?
C4 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
O2 C10 C11 106.98(13) . . ?
O2 C10 H10A 110.3 . . ?
C11 C10 H10A 110.3 . . ?
O2 C10 H10B 110.3 . . ?
C11 C10 H10B 110.3 . . ?
H10A C10 H10B 108.6 . . ?
C10 C11 C12 112.34(14) . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 110.72(14) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
N2 C13 C12 114.31(13) . . ?
N2 C13 H13A 108.7 . . ?
C12 C13 H13A 108.7 . . ?
N2 C13 H13B 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
N2 C14 C15 112.21(13) . . ?
N2 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
N2 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
N3 C15 C14 109.55(13) . . ?
N3 C15 H15A 109.8 . . ?
C14 C15 H15A 109.8 . . ?
N3 C15 H15B 109.8 . . ?
C14 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
N2 C16 C17 110.98(12) . . ?
N2 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
N2 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
N3 C17 C16 110.42(12) . . ?
N3 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
N3 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C23 C18 C19 116.81(13) . . ?
C23 C18 N3 123.32(13) . . ?
C19 C18 N3 119.82(12) . . ?
C20 C19 C18 121.01(13) . . ?
C20 C19 Cl1 119.27(11) . . ?
C18 C19 Cl1 119.59(10) . . ?
C21 C20 C19 120.80(14) . . ?
C21 C20 Cl2 118.79(12) . . ?
C19 C20 Cl2 120.40(11) . . ?
C22 C21 C20 118.57(14) . . ?
C22 C21 H21 120.7 . . ?
C20 C21 H21 120.7 . . ?
C21 C22 C23 121.41(15) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C22 C23 C18 121.29(15) . . ?
C22 C23 H23 119.4 . . ?
C18 C23 H23 119.4 . . ?
O3 C24 C25 123.09(16) . . ?
O3 C24 C29 116.86(17) . . ?
C25 C24 C29 120.04(16) . . ?
C24 C25 C26 119.73(17) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
O4 C26 C27 122.72(17) . . ?
O4 C26 C25 116.93(18) . . ?
C27 C26 C25 120.35(19) . . ?
C28 C27 C26 119.23(18) . . ?
C28 C27 H27 120.4 . . ?
C26 C27 H27 120.4 . . ?
C27 C28 C29 121.54(19) . . ?
C27 C28 H28 119.2 . . ?
C29 C28 H28 119.2 . . ?
C28 C29 C24 119.10(19) . . ?
C28 C29 H29 120.5 . . ?
C24 C29 H29 120.5 . . ?
C1 N1 C5 124.02(14) . . ?
C1 N1 H1N 115.7(12) . . ?
C5 N1 H1N 119.5(12) . . ?
C14 N2 C16 108.44(11) . . ?
C14 N2 C13 109.16(12) . . ?
C16 N2 C13 111.39(12) . . ?
C18 N3 C15 116.62(11) . . ?
C18 N3 C17 114.84(11) . . ?
C15 N3 C17 108.58(11) . . ?
C7 O2 C10 118.24(12) . . ?
C24 O3 H3O 111.3(18) . . ?
C26 O4 H4O 110.0(16) . . ?

_refine_diff_density_max         0.399
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_BA44M
_database_code_depnum_ccdc_archive 'CCDC 1430982'
_audit_update_record             
;
2015-10-13 deposited with the CCDC.
2016-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1:1 cocrystal of Aripiprazole Catechol Hydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H27 Cl2 N3 O2, C6 H6 O2, 0.293(O)'
_chemical_formula_sum            'C29 H33 Cl2 N3 O4.29'
_chemical_formula_weight         563.17

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      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                   14.7513(16)
_cell_length_b                   9.9206(11)
_cell_length_c                   20.9131(17)
_cell_angle_alpha                90
_cell_angle_beta                 111.104(6)
_cell_angle_gamma                90
_cell_volume                     2855.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6927
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      23.14

_exptl_crystal_description       Needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             1185
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.267
_shelx_estimated_absorpt_T_min   0.896
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26716
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.079
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_full        25.025
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5044
_reflns_number_gt                4124
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_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)+(0.0787P)²+1.3465P] 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         5044
_refine_ls_number_parameters     369
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0648
_refine_ls_wR_factor_ref         0.1647
_refine_ls_wR_factor_gt          0.1560
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.214
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C -0.0084(2) -0.1760(3) 0.44470(15) 0.0555(7) Uani 1 1 d . . . . .
C2 C -0.0067(3) -0.3097(4) 0.4114(2) 0.0772(10) Uani 1 1 d . . . . .
H2A H -0.0287 -0.2973 0.3622 0.093 Uiso 1 1 calc R U . . .
H2B H -0.0519 -0.3703 0.4209 0.093 Uiso 1 1 calc R U . . .
C3 C 0.0929(3) -0.3741(3) 0.4359(2) 0.0825(11) Uani 1 1 d . . . . .
H3A H 0.1092 -0.4054 0.4826 0.099 Uiso 1 1 calc R U . . .
H3B H 0.0925 -0.4513 0.4073 0.099 Uiso 1 1 calc R U . . .
C4 C 0.1681(2) -0.2739(3) 0.43276(18) 0.0625(8) Uani 1 1 d . . . . .
C5 C 0.15869(19) -0.1425(3) 0.45156(14) 0.0468(6) Uani 1 1 d . . . . .
C6 C 0.22619(18) -0.0450(3) 0.45290(13) 0.0452(6) Uani 1 1 d . . . . .
H6 H 0.2195 0.0424 0.4667 0.054 Uiso 1 1 calc R U . . .
C7 C 0.30386(19) -0.0783(3) 0.43359(14) 0.0492(7) Uani 1 1 d . . . . .
C8 C 0.3137(2) -0.2077(3) 0.41375(18) 0.0640(8) Uani 1 1 d . . . . .
H8 H 0.3655 -0.2303 0.4004 0.077 Uiso 1 1 calc R U . . .
C9 C 0.2462(3) -0.3036(3) 0.4137(2) 0.0718(10) Uani 1 1 d . . . . .
H9 H 0.2536 -0.3912 0.4005 0.086 Uiso 1 1 calc R U . . .
C10 C 0.4391(2) 0.0050(3) 0.40654(16) 0.0570(7) Uani 1 1 d . . . . .
H10A H 0.4112 -0.0334 0.3610 0.068 Uiso 1 1 calc R U . . .
H10B H 0.4880 -0.0565 0.4352 0.068 Uiso 1 1 calc R U . . .
C11 C 0.4833(2) 0.1393(3) 0.40362(17) 0.0610(8) Uani 1 1 d . . . . .
H11A H 0.5110 0.1759 0.4496 0.073 Uiso 1 1 calc R U . . .
H11B H 0.4328 0.2005 0.3765 0.073 Uiso 1 1 calc R U . . .
C12 C 0.5619(2) 0.1310(3) 0.37267(17) 0.0597(8) Uani 1 1 d . . . . .
H12A H 0.6117 0.0681 0.3989 0.072 Uiso 1 1 calc R U . . .
H12B H 0.5340 0.0976 0.3261 0.072 Uiso 1 1 calc R U . . .
C13 C 0.6071(2) 0.2680(3) 0.37259(18) 0.0629(8) Uani 1 1 d . . . . .
H13A H 0.5556 0.3343 0.3560 0.075 Uiso 1 1 calc R U . . .
H13B H 0.6464 0.2917 0.4194 0.075 Uiso 1 1 calc R U . . .
C14 C 0.6987(2) 0.4158(3) 0.32829(19) 0.0646(8) Uani 1 1 d . . . . .
H14A H 0.7327 0.4472 0.3747 0.077 Uiso 1 1 calc R U . . .
H14B H 0.6416 0.4718 0.3080 0.077 Uiso 1 1 calc R U . . .
C15 C 0.7643(2) 0.4309(3) 0.28748(17) 0.0596(8) Uani 1 1 d . . . . .
H15A H 0.7300 0.4028 0.2405 0.071 Uiso 1 1 calc R U . . .
H15B H 0.7828 0.5246 0.2871 0.071 Uiso 1 1 calc R U . . .
C16 C 0.7563(2) 0.1921(3) 0.35913(16) 0.0533(7) Uani 1 1 d . . . . .
H16A H 0.7378 0.0983 0.3593 0.064 Uiso 1 1 calc R U . . .
H16B H 0.7916 0.2191 0.4062 0.064 Uiso 1 1 calc R U . . .
C17 C 0.8209(2) 0.2070(3) 0.31810(16) 0.0499(7) Uani 1 1 d . . . . .
H17A H 0.8779 0.1506 0.3376 0.060 Uiso 1 1 calc R U . . .
H17B H 0.7864 0.1776 0.2714 0.060 Uiso 1 1 calc R U . . .
C18 C 0.92779(19) 0.3696(3) 0.29377(13) 0.0448(6) Uani 1 1 d . . . . .
C19 C 1.02155(19) 0.3242(3) 0.33219(13) 0.0448(6) Uani 1 1 d . . . . .
C20 C 1.0970(2) 0.3408(3) 0.30887(15) 0.0518(7) Uani 1 1 d . . . . .
C21 C 1.0835(2) 0.4098(3) 0.24902(16) 0.0629(8) Uani 1 1 d . . . . .
H21 H 1.1347 0.4220 0.2335 0.075 Uiso 1 1 calc R U . . .
C22 C 0.9929(2) 0.4601(4) 0.21272(16) 0.0680(9) Uani 1 1 d . . . . .
H22 H 0.9834 0.5095 0.1730 0.082 Uiso 1 1 calc R U . . .
C23 C 0.9159(2) 0.4390(3) 0.23373(15) 0.0594(8) Uani 1 1 d . . . . .
H23 H 0.8548 0.4718 0.2073 0.071 Uiso 1 1 calc R U . . .
C24 C 0.4931(3) 0.1743(5) 0.1599(2) 0.0816(11) Uani 1 1 d . . . . .
C25 C 0.4665(4) 0.1131(5) 0.0963(3) 0.1001(14) Uani 0.624(8) 1 d D . P A 1
C26 C 0.3741(5) 0.1315(6) 0.0483(3) 0.125(2) Uani 1 1 d . . . . .
H26 H 0.3560 0.0919 0.0052 0.151 Uiso 1 1 d R U . A .
C27 C 0.3086(5) 0.2110(7) 0.0662(4) 0.137(3) Uani 1 1 d . . . . .
H27 H 0.2459 0.2220 0.0345 0.164 Uiso 1 1 calc R U . . .
C28 C 0.3329(4) 0.2714(5) 0.1270(3) 0.1177(18) Uani 1 1 d . . . . .
H28 H 0.2888 0.3243 0.1383 0.141 Uiso 1 1 d R U . A .
C29 C 0.4285(3) 0.2512(5) 0.1732(3) 0.0928(13) Uani 0.624(8) 1 d . . P A 1
H29 H 0.4474 0.2942 0.2156 0.111 Uiso 0.624(8) 1 calc R U P A 1
C25D C 0.4665(4) 0.1131(5) 0.0963(3) 0.1001(14) Uani 0.376(8) 1 d . . P A 2
H25D H 0.5109 0.0595 0.0857 0.120 Uiso 0.376(8) 1 calc R U P A 2
C29D C 0.4285(3) 0.2512(5) 0.1732(3) 0.0928(13) Uani 0.376(8) 1 d D . P A 2
Cl1 Cl 1.04460(5) 0.25399(8) 0.41256(4) 0.0565(2) Uani 1 1 d . . . . .
Cl2 Cl 1.21202(6) 0.27941(10) 0.35580(5) 0.0784(3) Uani 1 1 d . . . . .
N1 N 0.07615(17) -0.1076(3) 0.46708(12) 0.0503(6) Uani 1 1 d D . . . .
H1N H 0.075(2) -0.036(2) 0.4870(13) 0.049(8) Uiso 1 1 d D . . . .
N2 N 0.66835(16) 0.2754(2) 0.33025(13) 0.0514(6) Uani 1 1 d . . . . .
N3 N 0.85085(15) 0.3482(2) 0.31808(12) 0.0464(5) Uani 1 1 d . . . . .
O1 O -0.08168(15) -0.1315(2) 0.45174(11) 0.0670(6) Uani 1 1 d . . . . .
O2 O 0.36497(14) 0.0264(2) 0.43476(11) 0.0602(5) Uani 1 1 d . . . . .
O3 O 0.5863(2) 0.1514(4) 0.20458(16) 0.1098(10) Uani 1 1 d D . . . .
H3O H 0.5975 0.1993 0.2385 0.165 Uiso 1 1 calc DR U . . .
O4 O 0.5299(4) 0.0307(6) 0.0819(3) 0.122(2) Uani 0.624(8) 1 d D . P A 1
H4O H 0.5725 0.0070 0.1177 0.183 Uiso 0.624(8) 1 calc DR U P A 1
O4D O 0.4570(7) 0.3179(11) 0.2342(5) 0.131(4) Uani 0.376(8) 1 d D . P A 2
H4D H 0.4113 0.3618 0.2366 0.196 Uiso 0.376(8) 1 calc DR U P A 2
O5W O 0.6701(8) -0.0624(13) 0.2273(7) 0.124(6) Uani 0.293(9) 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
C1 O1 1.224(4) . ?
C1 N1 1.348(4) . ?
C1 C2 1.503(5) . ?
C2 C3 1.512(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.508(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C9 1.381(4) . ?
C4 C5 1.383(4) . ?
C5 C6 1.381(4) . ?
C5 N1 1.411(3) . ?
C6 C7 1.385(4) . ?
C6 H6 0.9300 . ?
C7 O2 1.370(3) . ?
C7 C8 1.373(4) . ?
C8 C9 1.377(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 O2 1.433(3) . ?
C10 C11 1.494(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.520(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.514(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N2 1.477(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N2 1.469(4) . ?
C14 C15 1.510(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N3 1.458(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N2 1.472(4) . ?
C16 C17 1.502(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N3 1.469(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C23 1.387(4) . ?
C18 C19 1.400(4) . ?
C18 N3 1.417(3) . ?
C19 C20 1.377(4) . ?
C19 Cl1 1.736(3) . ?
C20 C21 1.376(4) . ?
C20 Cl2 1.736(3) . ?
C21 C22 1.371(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.374(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C29D 1.326(6) . ?
C24 C29 1.326(6) . ?
C24 O3 1.374(5) . ?
C24 C25D 1.385(6) . ?
C24 C25 1.385(6) . ?
C25 O4 1.355(6) . ?
C25 C26 1.383(7) . ?
C26 C25D 1.383(7) . ?
C26 C27 1.398(9) . ?
C26 H26 0.9299 . ?
C27 C28 1.334(9) . ?
C27 H27 0.9300 . ?
C28 C29D 1.407(7) . ?
C28 C29 1.407(7) . ?
C28 H28 0.9301 . ?
C29 H29 0.9300 . ?
C25D H25D 0.9300 . ?
C29D O4D 1.361(8) . ?
N1 H1N 0.826(17) . ?
O3 H3O 0.8200 . ?
O4 H4O 0.8200 . ?
O4D H4D 0.8200 . ?

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
O1 C1 N1 121.6(3) . . ?
O1 C1 C2 122.5(3) . . ?
N1 C1 C2 115.9(3) . . ?
C1 C2 C3 113.1(3) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C2 110.3(3) . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C9 C4 C5 117.5(3) . . ?
C9 C4 C3 125.2(3) . . ?
C5 C4 C3 117.3(3) . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 N1 119.9(2) . . ?
C4 C5 N1 118.6(3) . . ?
C5 C6 C7 119.5(3) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
O2 C7 C8 125.0(2) . . ?
O2 C7 C6 115.0(2) . . ?
C8 C7 C6 120.0(3) . . ?
C7 C8 C9 119.4(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C8 C9 C4 122.1(3) . . ?
C8 C9 H9 119.0 . . ?
C4 C9 H9 119.0 . . ?
O2 C10 C11 107.1(2) . . ?
O2 C10 H10A 110.3 . . ?
C11 C10 H10A 110.3 . . ?
O2 C10 H10B 110.3 . . ?
C11 C10 H10B 110.3 . . ?
H10A C10 H10B 108.6 . . ?
C10 C11 C12 112.3(3) . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 110.8(3) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
N2 C13 C12 114.2(2) . . ?
N2 C13 H13A 108.7 . . ?
C12 C13 H13A 108.7 . . ?
N2 C13 H13B 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
N2 C14 C15 111.9(2) . . ?
N2 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
N2 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
N3 C15 C14 109.5(2) . . ?
N3 C15 H15A 109.8 . . ?
C14 C15 H15A 109.8 . . ?
N3 C15 H15B 109.8 . . ?
C14 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
N2 C16 C17 110.9(2) . . ?
N2 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 108.0 . . ?
N3 C17 C16 110.3(2) . . ?
N3 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
N3 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C23 C18 C19 117.1(2) . . ?
C23 C18 N3 122.9(2) . . ?
C19 C18 N3 120.0(2) . . ?
C20 C19 C18 121.1(2) . . ?
C20 C19 Cl1 119.3(2) . . ?
C18 C19 Cl1 119.5(2) . . ?
C21 C20 C19 120.7(3) . . ?
C21 C20 Cl2 118.7(2) . . ?
C19 C20 Cl2 120.5(2) . . ?
C22 C21 C20 118.5(3) . . ?
C22 C21 H21 120.8 . . ?
C20 C21 H21 120.8 . . ?
C21 C22 C23 121.4(3) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C22 C23 C18 121.0(3) . . ?
C22 C23 H23 119.5 . . ?
C18 C23 H23 119.5 . . ?
C29D C24 O3 124.8(4) . . ?
C29 C24 O3 124.8(4) . . ?
C29D C24 C25D 118.5(5) . . ?
O3 C24 C25D 116.6(4) . . ?
C29 C24 C25 118.5(5) . . ?
O3 C24 C25 116.6(4) . . ?
O4 C25 C26 119.9(6) . . ?
O4 C25 C24 119.9(5) . . ?
C26 C25 C24 120.2(6) . . ?
C25D C26 C27 118.5(6) . . ?
C25 C26 C27 118.5(6) . . ?
C25D C26 H26 120.7 . . ?
C25 C26 H26 120.7 . . ?
C27 C26 H26 120.8 . . ?
C28 C27 C26 122.3(6) . . ?
C28 C27 H27 118.9 . . ?
C26 C27 H27 118.9 . . ?
C27 C28 C29D 116.7(7) . . ?
C27 C28 C29 116.7(7) . . ?
C27 C28 H28 121.6 . . ?
C29D C28 H28 121.7 . . ?
C29 C28 H28 121.7 . . ?
C24 C29 C28 123.8(6) . . ?
C24 C29 H29 118.1 . . ?
C28 C29 H29 118.1 . . ?
C26 C25D C24 120.2(6) . . ?
C26 C25D H25D 119.9 . . ?
C24 C25D H25D 119.9 . . ?
C24 C29D O4D 118.2(6) . . ?
C24 C29D C28 123.8(6) . . ?
O4D C29D C28 118.0(6) . . ?
C1 N1 C5 124.4(3) . . ?
C1 N1 H1N 115(2) . . ?
C5 N1 H1N 120(2) . . ?
C14 N2 C16 108.2(2) . . ?
C14 N2 C13 108.8(2) . . ?
C16 N2 C13 111.4(2) . . ?
C18 N3 C15 116.6(2) . . ?
C18 N3 C17 115.0(2) . . ?
C15 N3 C17 108.7(2) . . ?
C7 O2 C10 118.4(2) . . ?
C24 O3 H3O 109.5 . . ?
C25 O4 H4O 109.5 . . ?
C29D O4D H4D 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -153.3(3) . . . . ?
N1 C1 C2 C3 26.2(4) . . . . ?
C1 C2 C3 C4 -49.3(4) . . . . ?
C2 C3 C4 C9 -141.9(4) . . . . ?
C2 C3 C4 C5 39.2(5) . . . . ?
C9 C4 C5 C6 -1.5(5) . . . . ?
C3 C4 C5 C6 177.4(3) . . . . ?
C9 C4 C5 N1 176.1(3) . . . . ?
C3 C4 C5 N1 -5.0(5) . . . . ?
C4 C5 C6 C7 1.5(4) . . . . ?
N1 C5 C6 C7 -176.1(2) . . . . ?
C5 C6 C7 O2 178.1(2) . . . . ?
C5 C6 C7 C8 -0.4(4) . . . . ?
O2 C7 C8 C9 -178.9(3) . . . . ?
C6 C7 C8 C9 -0.4(5) . . . . ?
C7 C8 C9 C4 0.3(6) . . . . ?
C5 C4 C9 C8 0.6(6) . . . . ?
C3 C4 C9 C8 -178.2(4) . . . . ?
O2 C10 C11 C12 -178.5(2) . . . . ?
C10 C11 C12 C13 -178.2(3) . . . . ?
C11 C12 C13 N2 -167.3(3) . . . . ?
N2 C14 C15 N3 -59.6(3) . . . . ?
N2 C16 C17 N3 60.0(3) . . . . ?
C23 C18 C19 C20 -4.0(4) . . . . ?
N3 C18 C19 C20 178.4(2) . . . . ?
C23 C18 C19 Cl1 172.6(2) . . . . ?
N3 C18 C19 Cl1 -5.0(3) . . . . ?
C18 C19 C20 C21 3.9(4) . . . . ?
Cl1 C19 C20 C21 -172.6(2) . . . . ?
C18 C19 C20 Cl2 -178.0(2) . . . . ?
Cl1 C19 C20 Cl2 5.5(3) . . . . ?
C19 C20 C21 C22 -0.8(5) . . . . ?
Cl2 C20 C21 C22 -178.9(3) . . . . ?
C20 C21 C22 C23 -2.2(5) . . . . ?
C21 C22 C23 C18 2.1(5) . . . . ?
C19 C18 C23 C22 1.0(4) . . . . ?
N3 C18 C23 C22 178.5(3) . . . . ?
C29 C24 C25 O4 -178.0(4) . . . . ?
O3 C24 C25 O4 2.8(6) . . . . ?
C29 C24 C25 C26 -0.6(6) . . . . ?
O3 C24 C25 C26 -179.8(4) . . . . ?
O4 C25 C26 C27 176.4(5) . . . . ?
C24 C25 C26 C27 -1.0(7) . . . . ?
C25D C26 C27 C28 1.4(8) . . . . ?
C25 C26 C27 C28 1.4(8) . . . . ?
C26 C27 C28 C29D -0.3(8) . . . . ?
C26 C27 C28 C29 -0.3(8) . . . . ?
O3 C24 C29 C28 -179.0(4) . . . . ?
C25 C24 C29 C28 1.9(6) . . . . ?
C27 C28 C29 C24 -1.5(7) . . . . ?
C27 C26 C25D C24 -1.0(7) . . . . ?
C29D C24 C25D C26 -0.6(6) . . . . ?
O3 C24 C25D C26 -179.8(4) . . . . ?
O3 C24 C29D O4D 3.3(8) . . . . ?
C25D C24 C29D O4D -175.8(6) . . . . ?
O3 C24 C29D C28 -179.0(4) . . . . ?
C25D C24 C29D C28 1.9(6) . . . . ?
C27 C28 C29D C24 -1.5(7) . . . . ?
C27 C28 C29D O4D 176.3(7) . . . . ?
O1 C1 N1 C5 -169.9(3) . . . . ?
C2 C1 N1 C5 10.6(4) . . . . ?
C6 C5 N1 C1 155.0(3) . . . . ?
C4 C5 N1 C1 -22.6(4) . . . . ?
C15 C14 N2 C16 57.2(3) . . . . ?
C15 C14 N2 C13 178.3(3) . . . . ?
C17 C16 N2 C14 -57.0(3) . . . . ?
C17 C16 N2 C13 -176.6(2) . . . . ?
C12 C13 N2 C14 173.8(3) . . . . ?
C12 C13 N2 C16 -67.1(3) . . . . ?
C23 C18 N3 C15 -15.3(4) . . . . ?
C19 C18 N3 C15 162.2(3) . . . . ?
C23 C18 N3 C17 113.6(3) . . . . ?
C19 C18 N3 C17 -68.9(3) . . . . ?
C14 C15 N3 C18 -168.8(2) . . . . ?
C14 C15 N3 C17 59.3(3) . . . . ?
C16 C17 N3 C18 167.0(2) . . . . ?
C16 C17 N3 C15 -60.2(3) . . . . ?
C8 C7 O2 C10 7.0(4) . . . . ?
C6 C7 O2 C10 -171.5(2) . . . . ?
C11 C10 O2 C7 170.7(2) . . . . ?

_refine_diff_density_max         0.506
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_AZ62M
_database_code_depnum_ccdc_archive 'CCDC 1430983'
_audit_update_record             
;
2015-10-13 deposited with the CCDC.
2016-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1:1 cocrystal of Aripiprazole and Hydroquinone'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H27 Cl2 N3 O2, C6 H6 O2'
_chemical_formula_sum            'C29 H33 Cl2 N3 O4'
_chemical_formula_weight         558.48

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                   6.9061(8)
_cell_length_b                   9.4544(11)
_cell_length_c                   22.484(3)
_cell_angle_alpha                96.056(2)
_cell_angle_beta                 95.355(2)
_cell_angle_gamma                100.696(2)
_cell_volume                     1424.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4076
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      22.85

_exptl_crystal_description       Needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.267
_shelx_estimated_absorpt_T_min   0.889
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14353
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.834
_diffrn_reflns_theta_max         25.680
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5395
_reflns_number_gt                3513
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_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)+(0.0659P)²+0.2349P] 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         5395
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1348
_refine_ls_wR_factor_gt          0.1177
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
C1 C 1.6630(4) 0.7005(3) 0.99305(12) 0.0568(6) Uani 1 1 d . . . . .
C2 C 1.8082(4) 0.8117(4) 0.97045(15) 0.0890(10) Uani 1 1 d . . . . .
H2A H 1.8513 0.7685 0.9342 0.107 Uiso 1 1 calc R U . . .
H2B H 1.9235 0.8414 1.0003 0.107 Uiso 1 1 calc R U . . .
C3 C 1.7302(4) 0.9434(3) 0.95670(14) 0.0757(8) Uani 1 1 d . . . . .
H3A H 1.8210 1.0005 0.9339 0.091 Uiso 1 1 calc R U . . .
H3B H 1.7229 1.0025 0.9941 0.091 Uiso 1 1 calc R U . . .
C4 C 1.5285(4) 0.9034(3) 0.92134(12) 0.0573(6) Uani 1 1 d . . . . .
C5 C 1.4064(3) 0.7725(2) 0.92817(11) 0.0503(6) Uani 1 1 d . . . . .
C6 C 1.2210(3) 0.7303(2) 0.89694(11) 0.0543(6) Uani 1 1 d . . . . .
H6 H 1.1428 0.6417 0.9015 0.065 Uiso 1 1 calc R U . . .
C7 C 1.1496(4) 0.8191(2) 0.85870(11) 0.0551(6) Uani 1 1 d . . . . .
C8 C 1.2669(4) 0.9501(3) 0.85186(13) 0.0695(7) Uani 1 1 d . . . . .
H8 H 1.2202 1.0113 0.8267 0.083 Uiso 1 1 calc R U . . .
C9 C 1.4540(4) 0.9885(3) 0.88293(14) 0.0743(8) Uani 1 1 d . . . . .
H9 H 1.5334 1.0761 0.8776 0.089 Uiso 1 1 calc R U . . .
C10 C 0.8687(4) 0.8619(3) 0.79681(12) 0.0679(7) Uani 1 1 d . . . . .
H10A H 0.9458 0.8906 0.7646 0.081 Uiso 1 1 calc R U . . .
H10B H 0.8598 0.9486 0.8227 0.081 Uiso 1 1 calc R U . . .
C11 C 0.6653(4) 0.7814(3) 0.77117(12) 0.0707(8) Uani 1 1 d . . . . .
H11A H 0.5933 0.8483 0.7534 0.085 Uiso 1 1 calc R U . . .
H11B H 0.5950 0.7456 0.8036 0.085 Uiso 1 1 calc R U . . .
C12 C 0.6658(4) 0.6556(3) 0.72419(11) 0.0632(7) Uani 1 1 d . . . . .
H12A H 0.7300 0.5850 0.7424 0.076 Uiso 1 1 calc R U . . .
H12B H 0.7420 0.6898 0.6926 0.076 Uiso 1 1 calc R U . . .
C13 C 0.4578(4) 0.5829(3) 0.69687(11) 0.0628(7) Uani 1 1 d . . . . .
H13A H 0.3802 0.5557 0.7291 0.075 Uiso 1 1 calc R U . . .
H13B H 0.3977 0.6529 0.6770 0.075 Uiso 1 1 calc R U . . .
C14 C 0.2372(4) 0.3927(3) 0.63149(11) 0.0626(7) Uani 1 1 d . . . . .
H14A H 0.1765 0.4674 0.6154 0.075 Uiso 1 1 calc R U . . .
H14B H 0.1679 0.3622 0.6650 0.075 Uiso 1 1 calc R U . . .
C15 C 0.2145(4) 0.2656(3) 0.58357(11) 0.0630(7) Uani 1 1 d . . . . .
H15A H 0.2675 0.1880 0.6000 0.076 Uiso 1 1 calc R U . . .
H15B H 0.0749 0.2296 0.5697 0.076 Uiso 1 1 calc R U . . .
C16 C 0.5527(4) 0.4900(3) 0.60211(11) 0.0577(6) Uani 1 1 d . . . . .
H16A H 0.6924 0.5246 0.6161 0.069 Uiso 1 1 calc R U . . .
H16B H 0.5031 0.5679 0.5848 0.069 Uiso 1 1 calc R U . . .
C17 C 0.5300(3) 0.3619(3) 0.55424(11) 0.0571(6) Uani 1 1 d . . . . .
H17A H 0.6022 0.3903 0.5210 0.069 Uiso 1 1 calc R U . . .
H17B H 0.5846 0.2850 0.5707 0.069 Uiso 1 1 calc R U . . .
C18 C 0.2759(3) 0.2107(2) 0.47987(10) 0.0480(5) Uani 1 1 d . . . . .
C19 C 0.0970(3) 0.2004(2) 0.44335(11) 0.0494(6) Uani 1 1 d . . . . .
C20 C 0.0501(3) 0.1066(3) 0.39029(11) 0.0543(6) Uani 1 1 d . . . . .
C21 C 0.1803(4) 0.0222(3) 0.37152(12) 0.0611(7) Uani 1 1 d . . . . .
H21 H 0.1483 -0.0416 0.3360 0.073 Uiso 1 1 calc R U . . .
C22 C 0.3572(4) 0.0338(3) 0.40594(13) 0.0658(7) Uani 1 1 d . . . . .
H22 H 0.4474 -0.0215 0.3932 0.079 Uiso 1 1 calc R U . . .
C23 C 0.4049(4) 0.1252(3) 0.45883(12) 0.0602(7) Uani 1 1 d . . . . .
H23 H 0.5267 0.1304 0.4813 0.072 Uiso 1 1 calc R U . . .
C24 C 0.7134(5) 0.2898(3) 0.76203(12) 0.0701(8) Uani 1 1 d . . . . .
C25 C 0.5903(4) 0.3360(3) 0.80106(12) 0.0669(7) Uani 1 1 d . . . . .
H25 H 0.4635 0.3452 0.7862 0.080 Uiso 1 1 calc R U . . .
C26 C 0.6512(4) 0.3692(3) 0.86205(11) 0.0608(6) Uani 1 1 d . . . . .
H26 H 0.5664 0.4018 0.8878 0.073 Uiso 1 1 calc R U . . .
C27 C 0.8368(4) 0.3540(2) 0.88462(11) 0.0542(6) Uani 1 1 d . . . . .
C28 C 0.9587(4) 0.3043(3) 0.84575(12) 0.0664(7) Uani 1 1 d . . . . .
H28 H 1.0838 0.2918 0.8607 0.080 Uiso 1 1 calc R U . . .
C29 C 0.8979(5) 0.2731(3) 0.78525(12) 0.0752(8) Uani 1 1 d . . . . .
H29 H 0.9825 0.2401 0.7596 0.090 Uiso 1 1 calc R U . . .
Cl1 Cl -0.06122(10) 0.31458(8) 0.46317(3) 0.0783(3) Uani 1 1 d . . . . .
Cl2 Cl -0.16940(10) 0.09638(9) 0.34473(3) 0.0823(3) Uani 1 1 d . . . . .
H1N H 1.400(4) 0.617(3) 0.9779(13) 0.085(10) Uiso 1 1 d . . . . .
H3O H 0.582(5) 0.311(4) 0.6907(15) 0.106(12) Uiso 1 1 d . . . . .
H4O H 1.005(4) 0.382(3) 0.9508(13) 0.082(10) Uiso 1 1 d . . . . .
N1 N 1.4761(3) 0.6854(2) 0.96909(11) 0.0637(6) Uani 1 1 d . . . . .
N2 N 0.4459(3) 0.4533(2) 0.65331(8) 0.0543(5) Uani 1 1 d . . . . .
N3 N 0.3207(3) 0.3099(2) 0.53273(8) 0.0510(5) Uani 1 1 d . . . . .
O1 O 1.7152(2) 0.6202(2) 1.02891(9) 0.0723(5) Uani 1 1 d . . . . .
O2 O 0.9615(3) 0.76787(17) 0.83047(8) 0.0662(5) Uani 1 1 d . . . . .
O3 O 0.6592(4) 0.2583(3) 0.70113(9) 0.1095(10) Uani 1 1 d . . . . .
O4 O 0.8898(3) 0.3886(2) 0.94510(9) 0.0790(6) Uani 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
C1 O1 1.238(3) . ?
C1 N1 1.328(3) . ?
C1 C2 1.478(4) . ?
C2 C3 1.494(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.501(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C9 1.369(4) . ?
C4 C5 1.394(3) . ?
C5 C6 1.369(3) . ?
C5 N1 1.407(3) . ?
C6 C7 1.383(3) . ?
C6 H6 0.9300 . ?
C7 O2 1.368(3) . ?
C7 C8 1.380(3) . ?
C8 C9 1.376(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 O2 1.427(3) . ?
C10 C11 1.498(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.506(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.514(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N2 1.470(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N2 1.466(3) . ?
C14 C15 1.502(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N3 1.471(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N2 1.462(3) . ?
C16 C17 1.508(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N3 1.456(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C23 1.391(3) . ?
C18 C19 1.400(3) . ?
C18 N3 1.406(3) . ?
C19 C20 1.383(3) . ?
C19 Cl1 1.728(2) . ?
C20 C21 1.374(3) . ?
C20 Cl2 1.730(2) . ?
C21 C22 1.364(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.369(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 O3 1.371(3) . ?
C24 C25 1.371(4) . ?
C24 C29 1.374(4) . ?
C25 C26 1.381(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.373(3) . ?
C26 H26 0.9300 . ?
C27 O4 1.363(3) . ?
C27 C28 1.375(4) . ?
C28 C29 1.370(4) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
N1 H1N 0.81(3) . ?
O3 H3O 0.83(3) . ?
O4 H4O 0.81(3) . ?

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
O1 C1 N1 122.3(2) . . ?
O1 C1 C2 121.8(2) . . ?
N1 C1 C2 115.7(3) . . ?
C1 C2 C3 114.2(2) . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C2 C3 C4 111.5(2) . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C9 C4 C5 117.3(2) . . ?
C9 C4 C3 124.1(2) . . ?
C5 C4 C3 118.6(2) . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 N1 120.4(2) . . ?
C4 C5 N1 118.5(2) . . ?
C5 C6 C7 120.3(2) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
O2 C7 C8 124.8(2) . . ?
O2 C7 C6 115.6(2) . . ?
C8 C7 C6 119.6(2) . . ?
C9 C8 C7 118.9(2) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C4 C9 C8 122.8(2) . . ?
C4 C9 H9 118.6 . . ?
C8 C9 H9 118.6 . . ?
O2 C10 C11 108.0(2) . . ?
O2 C10 H10A 110.1 . . ?
C11 C10 H10A 110.1 . . ?
O2 C10 H10B 110.1 . . ?
C11 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
C10 C11 C12 113.6(2) . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 111.9(2) . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
N2 C13 C12 114.9(2) . . ?
N2 C13 H13A 108.5 . . ?
C12 C13 H13A 108.5 . . ?
N2 C13 H13B 108.5 . . ?
C12 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
N2 C14 C15 112.1(2) . . ?
N2 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
N2 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
N3 C15 C14 109.8(2) . . ?
N3 C15 H15A 109.7 . . ?
C14 C15 H15A 109.7 . . ?
N3 C15 H15B 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
N2 C16 C17 112.1(2) . . ?
N2 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
N2 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
N3 C17 C16 109.53(19) . . ?
N3 C17 H17A 109.8 . . ?
C16 C17 H17A 109.8 . . ?
N3 C17 H17B 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
C23 C18 C19 116.3(2) . . ?
C23 C18 N3 123.9(2) . . ?
C19 C18 N3 119.71(19) . . ?
C20 C19 C18 121.3(2) . . ?
C20 C19 Cl1 119.61(17) . . ?
C18 C19 Cl1 118.99(18) . . ?
C21 C20 C19 120.6(2) . . ?
C21 C20 Cl2 118.3(2) . . ?
C19 C20 Cl2 121.10(18) . . ?
C22 C21 C20 118.7(2) . . ?
C22 C21 H21 120.7 . . ?
C20 C21 H21 120.7 . . ?
C21 C22 C23 121.3(2) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C22 C23 C18 121.7(2) . . ?
C22 C23 H23 119.2 . . ?
C18 C23 H23 119.2 . . ?
O3 C24 C25 122.7(3) . . ?
O3 C24 C29 118.9(3) . . ?
C25 C24 C29 118.4(2) . . ?
C24 C25 C26 121.2(3) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C27 C26 C25 119.9(3) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
O4 C27 C26 117.6(2) . . ?
O4 C27 C28 123.4(2) . . ?
C26 C27 C28 119.0(2) . . ?
C29 C28 C27 120.7(3) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C28 C29 C24 120.8(3) . . ?
C28 C29 H29 119.6 . . ?
C24 C29 H29 119.6 . . ?
C1 N1 C5 125.3(2) . . ?
C1 N1 H1N 115(2) . . ?
C5 N1 H1N 119(2) . . ?
C16 N2 C14 109.02(18) . . ?
C16 N2 C13 110.7(2) . . ?
C14 N2 C13 109.13(19) . . ?
C18 N3 C17 116.71(18) . . ?
C18 N3 C15 115.14(19) . . ?
C17 N3 C15 108.89(18) . . ?
C7 O2 C10 118.44(19) . . ?
C24 O3 H3O 109(2) . . ?
C27 O4 H4O 106(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
O1 C1 C2 C3 -148.9(3) . . . . ?
N1 C1 C2 C3 35.9(4) . . . . ?
C1 C2 C3 C4 -46.2(4) . . . . ?
C2 C3 C4 C9 -153.1(3) . . . . ?
C2 C3 C4 C5 27.8(3) . . . . ?
C9 C4 C5 C6 1.0(4) . . . . ?
C3 C4 C5 C6 -179.9(2) . . . . ?
C9 C4 C5 N1 -177.6(2) . . . . ?
C3 C4 C5 N1 1.6(3) . . . . ?
C4 C5 C6 C7 -1.3(4) . . . . ?
N1 C5 C6 C7 177.2(2) . . . . ?
C5 C6 C7 O2 -178.9(2) . . . . ?
C5 C6 C7 C8 0.5(4) . . . . ?
O2 C7 C8 C9 -179.9(2) . . . . ?
C6 C7 C8 C9 0.7(4) . . . . ?
C5 C4 C9 C8 0.3(4) . . . . ?
C3 C4 C9 C8 -178.8(3) . . . . ?
C7 C8 C9 C4 -1.1(4) . . . . ?
O2 C10 C11 C12 -67.1(3) . . . . ?
C10 C11 C12 C13 -176.6(2) . . . . ?
C11 C12 C13 N2 -176.3(2) . . . . ?
N2 C14 C15 N3 -58.3(3) . . . . ?
N2 C16 C17 N3 59.2(2) . . . . ?
C23 C18 C19 C20 1.9(3) . . . . ?
N3 C18 C19 C20 178.4(2) . . . . ?
C23 C18 C19 Cl1 -174.44(18) . . . . ?
N3 C18 C19 Cl1 2.0(3) . . . . ?
C18 C19 C20 C21 -1.0(4) . . . . ?
Cl1 C19 C20 C21 175.38(19) . . . . ?
C18 C19 C20 Cl2 -178.97(17) . . . . ?
Cl1 C19 C20 Cl2 -2.6(3) . . . . ?
C19 C20 C21 C22 -0.7(4) . . . . ?
Cl2 C20 C21 C22 177.40(19) . . . . ?
C20 C21 C22 C23 1.2(4) . . . . ?
C21 C22 C23 C18 -0.2(4) . . . . ?
C19 C18 C23 C22 -1.4(3) . . . . ?
N3 C18 C23 C22 -177.7(2) . . . . ?
O3 C24 C25 C26 -178.9(3) . . . . ?
C29 C24 C25 C26 1.9(4) . . . . ?
C24 C25 C26 C27 -1.0(4) . . . . ?
C25 C26 C27 O4 179.8(2) . . . . ?
C25 C26 C27 C28 -0.6(4) . . . . ?
O4 C27 C28 C29 -179.1(3) . . . . ?
C26 C27 C28 C29 1.3(4) . . . . ?
C27 C28 C29 C24 -0.3(4) . . . . ?
O3 C24 C29 C28 179.5(3) . . . . ?
C25 C24 C29 C28 -1.2(4) . . . . ?
O1 C1 N1 C5 180.0(2) . . . . ?
C2 C1 N1 C5 -4.8(4) . . . . ?
C6 C5 N1 C1 166.6(2) . . . . ?
C4 C5 N1 C1 -14.8(4) . . . . ?
C17 C16 N2 C14 -55.4(3) . . . . ?
C17 C16 N2 C13 -175.50(18) . . . . ?
C15 C14 N2 C16 55.1(3) . . . . ?
C15 C14 N2 C13 176.1(2) . . . . ?
C12 C13 N2 C16 -61.1(3) . . . . ?
C12 C13 N2 C14 178.9(2) . . . . ?
C23 C18 N3 C17 22.0(3) . . . . ?
C19 C18 N3 C17 -154.2(2) . . . . ?
C23 C18 N3 C15 -107.6(3) . . . . ?
C19 C18 N3 C15 76.3(3) . . . . ?
C16 C17 N3 C18 167.39(19) . . . . ?
C16 C17 N3 C15 -60.2(2) . . . . ?
C14 C15 N3 C18 -166.74(19) . . . . ?
C14 C15 N3 C17 60.0(3) . . . . ?
C8 C7 O2 C10 -7.6(4) . . . . ?
C6 C7 O2 C10 171.8(2) . . . . ?
C11 C10 O2 C7 -179.5(2) . . . . ?

_refine_diff_density_max         0.399
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_AS36M
_database_code_depnum_ccdc_archive 'CCDC 1430984'
_audit_update_record             
;
2015-10-13 deposited with the CCDC.
2016-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1:1 cocrystal of Aripiprazole Pyrograllol Hydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H27 Cl2 N3 O2, C6 H6 O3, 0.256(O)'
_chemical_formula_sum            'C29 H33 Cl2 N3 O5.26'
_chemical_formula_weight         578.58

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      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                   14.7016(11)
_cell_length_b                   9.9378(7)
_cell_length_c                   20.9827(12)
_cell_angle_alpha                90
_cell_angle_beta                 111.121(4)
_cell_angle_gamma                90
_cell_volume                     2859.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7629
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      28.11

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.271
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26964
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.076
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5420
_reflns_number_gt                4820
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_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)+(0.0561P)²+0.5696P] 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         5420
_refine_ls_number_parameters     378
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0977
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
H3O H 0.097(2) 0.706(3) 0.2430(16) 0.132(11) Uiso 1 1 d . . . . .
O6W O -0.1647(4) 0.9444(6) 0.2802(3) 0.091(2) Uani 0.256(5) 1 d . . . . .
H4O H -0.103(2) 0.868(3) 0.2326(14) 0.118(9) Uiso 1 1 d . . . . .
C1 C -0.50913(10) 0.32362(15) 0.44370(7) 0.0446(3) Uani 1 1 d . . . . .
C2 C -0.50984(12) 0.19160(18) 0.40875(9) 0.0624(4) Uani 1 1 d . . . . .
H2A H -0.5320 0.2062 0.3598 0.075 Uiso 1 1 calc R U . . .
H2B H -0.5557 0.1313 0.4178 0.075 Uiso 1 1 calc R U . . .
C3 C -0.40960(14) 0.12550(17) 0.43255(11) 0.0704(5) Uani 1 1 d . . . . .
H3A H -0.3931 0.0929 0.4789 0.084 Uiso 1 1 calc R U . . .
H3B H -0.4108 0.0492 0.4035 0.084 Uiso 1 1 calc R U . . .
C4 C -0.33389(12) 0.22477(15) 0.42991(8) 0.0524(4) Uani 1 1 d . . . . .
C5 C -0.34226(9) 0.35620(13) 0.44982(6) 0.0395(3) Uani 1 1 d . . . . .
C6 C -0.27418(9) 0.45364(13) 0.45222(6) 0.0400(3) Uani 1 1 d . . . . .
H6 H -0.2802 0.5402 0.4671 0.048 Uiso 1 1 calc R U . . .
C7 C -0.19661(9) 0.42081(14) 0.43213(7) 0.0436(3) Uani 1 1 d . . . . .
C8 C -0.18765(12) 0.29155(17) 0.41051(8) 0.0555(4) Uani 1 1 d . . . . .
H8 H -0.1363 0.2695 0.3965 0.067 Uiso 1 1 calc R U . . .
C9 C -0.25612(13) 0.19542(16) 0.41007(9) 0.0611(4) Uani 1 1 d . . . . .
H9 H -0.2495 0.1084 0.3960 0.073 Uiso 1 1 calc R U . . .
C10 C -0.06012(10) 0.50428(16) 0.40641(7) 0.0502(3) Uani 1 1 d . . . . .
H10A H -0.0880 0.4679 0.3605 0.060 Uiso 1 1 calc R U . . .
H10B H -0.0115 0.4417 0.4344 0.060 Uiso 1 1 calc R U . . .
C11 C -0.01470(10) 0.63900(16) 0.40523(8) 0.0528(4) Uani 1 1 d . . . . .
H11A H 0.0139 0.6729 0.4516 0.063 Uiso 1 1 calc R U . . .
H11B H -0.0650 0.7016 0.3793 0.063 Uiso 1 1 calc R U . . .
C12 C 0.06362(10) 0.63213(16) 0.37378(8) 0.0504(3) Uani 1 1 d . . . . .
H12A H 0.1132 0.5678 0.3988 0.060 Uiso 1 1 calc R U . . .
H12B H 0.0349 0.6015 0.3268 0.060 Uiso 1 1 calc R U . . .
C13 C 0.11004(11) 0.76879(15) 0.37558(8) 0.0481(3) Uani 1 1 d . . . . .
H13A H 0.0590 0.8363 0.3609 0.058 Uiso 1 1 calc R U . . .
H13B H 0.1509 0.7892 0.4224 0.058 Uiso 1 1 calc R U . . .
C14 C 0.19973(11) 0.91855(14) 0.33007(9) 0.0510(3) Uani 1 1 d . . . . .
H14A H 0.2345 0.9497 0.3763 0.061 Uiso 1 1 calc R U . . .
H14B H 0.1422 0.9743 0.3104 0.061 Uiso 1 1 calc R U . . .
C15 C 0.26464(10) 0.93410(14) 0.28852(8) 0.0491(3) Uani 1 1 d . . . . .
H15A H 0.2294 0.9072 0.2416 0.059 Uiso 1 1 calc R U . . .
H15B H 0.2837 1.0276 0.2886 0.059 Uiso 1 1 calc R U . . .
C16 C 0.25698(9) 0.69386(14) 0.35937(8) 0.0447(3) Uani 1 1 d . . . . .
H16A H 0.2379 0.6004 0.3591 0.054 Uiso 1 1 calc R U . . .
H16B H 0.2936 0.7194 0.4063 0.054 Uiso 1 1 calc R U . . .
C17 C 0.32052(9) 0.70923(13) 0.31723(8) 0.0430(3) Uani 1 1 d . . . . .
H17A H 0.3775 0.6520 0.3356 0.052 Uiso 1 1 calc R U . . .
H17B H 0.2846 0.6815 0.2706 0.052 Uiso 1 1 calc R U . . .
C18 C 0.42814(9) 0.87147(13) 0.29400(7) 0.0393(3) Uani 1 1 d . . . . .
C19 C 0.52203(9) 0.82393(13) 0.33250(6) 0.0394(3) Uani 1 1 d . . . . .
C20 C 0.59846(10) 0.84050(14) 0.30939(7) 0.0458(3) Uani 1 1 d . . . . .
C21 C 0.58575(11) 0.91054(17) 0.24992(8) 0.0561(4) Uani 1 1 d . . . . .
H21 H 0.6374 0.9222 0.2347 0.067 Uiso 1 1 calc R U . . .
C22 C 0.49512(12) 0.96259(18) 0.21367(8) 0.0589(4) Uani 1 1 d . . . . .
H22 H 0.4862 1.0126 0.1744 0.071 Uiso 1 1 calc R U . . .
C23 C 0.41733(10) 0.94205(16) 0.23443(7) 0.0506(3) Uani 1 1 d . . . . .
H23 H 0.3564 0.9760 0.2081 0.061 Uiso 1 1 calc R U . . .
C24 C -0.00640(11) 0.67858(19) 0.15911(8) 0.0611(4) Uani 1 1 d . . . . .
C25 C -0.07589(12) 0.75615(18) 0.17131(9) 0.0612(4) Uani 1 1 d . . . . .
C26 C -0.16941(14) 0.76668(18) 0.12225(10) 0.0697(5) Uani 1 1 d . . . . .
C27 C -0.19236(16) 0.7038(2) 0.06009(11) 0.0834(6) Uani 1 1 d . . . . .
H27 H -0.2544 0.7121 0.0270 0.100 Uiso 1 1 calc R U . . .
C28 C -0.12225(17) 0.6287(2) 0.04753(10) 0.0850(6) Uani 1 1 d . . . . .
H28 H -0.1373 0.5868 0.0053 0.102 Uiso 1 1 calc R U . . .
C29 C -0.02916(14) 0.6139(2) 0.09660(9) 0.0736(5) Uani 1 1 d . . . . .
H29 H 0.0172 0.5614 0.0876 0.088 Uiso 1 1 calc R U . . .
Cl1 Cl 0.54440(3) 0.75321(4) 0.41213(2) 0.04928(11) Uani 1 1 d . . . . .
Cl2 Cl 0.71309(3) 0.77689(5) 0.35626(3) 0.06912(14) Uani 1 1 d . . . . .
H5O H -0.2928(18) 0.844(2) 0.1106(12) 0.092(7) Uiso 1 1 d . . . . .
N1 N -0.42459(8) 0.39089(13) 0.46607(6) 0.0416(2) Uani 1 1 d . . . . .
H1N H -0.4234(11) 0.4621(17) 0.4860(8) 0.046(4) Uiso 1 1 d . . . . .
N2 N 0.16953(8) 0.77817(11) 0.33216(6) 0.0410(2) Uani 1 1 d . . . . .
N3 N 0.35125(8) 0.85023(11) 0.31808(6) 0.0401(2) Uani 1 1 d . . . . .
O1 O -0.58241(7) 0.36969(11) 0.45195(5) 0.0526(3) Uani 1 1 d . . . . .
O2 O -0.13472(7) 0.52465(11) 0.43443(6) 0.0542(3) Uani 1 1 d . . . . .
O3 O 0.08508(8) 0.66273(18) 0.20593(7) 0.0793(4) Uani 1 1 d . . . . .
O4 O -0.05144(10) 0.82171(18) 0.23271(7) 0.0827(4) Uani 1 1 d . . . . .
O5 O -0.23351(11) 0.84273(16) 0.14103(9) 0.0947(5) Uani 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
C1 O1 1.2389(17) . ?
C1 N1 1.3384(17) . ?
C1 C2 1.501(2) . ?
C2 C3 1.524(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.503(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C9 1.381(2) . ?
C4 C5 1.390(2) . ?
C5 C6 1.3804(18) . ?
C5 N1 1.4135(16) . ?
C6 C7 1.3897(17) . ?
C6 H6 0.9300 . ?
C7 O2 1.3651(17) . ?
C7 C8 1.384(2) . ?
C8 C9 1.385(2) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 O2 1.4332(15) . ?
C10 C11 1.500(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.5210(18) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.514(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N2 1.4759(17) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N2 1.4694(18) . ?
C14 C15 1.515(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N3 1.4601(17) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N2 1.4670(17) . ?
C16 C17 1.5077(18) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N3 1.4704(17) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C23 1.3917(19) . ?
C18 C19 1.4062(18) . ?
C18 N3 1.4104(16) . ?
C19 C20 1.3847(18) . ?
C19 Cl1 1.7314(13) . ?
C20 C21 1.381(2) . ?
C20 Cl2 1.7356(14) . ?
C21 C22 1.375(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(2) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 O3 1.359(2) . ?
C24 C25 1.375(3) . ?
C24 C29 1.389(3) . ?
C25 O4 1.371(2) . ?
C25 C26 1.393(2) . ?
C26 O5 1.372(3) . ?
C26 C27 1.374(3) . ?
C27 C28 1.373(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.393(3) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
N1 H1N 0.819(16) . ?
O3 H3O 0.85(3) . ?
O4 H4O 0.89(3) . ?
O5 H5O 0.88(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
O1 C1 N1 120.72(13) . . ?
O1 C1 C2 122.54(12) . . ?
N1 C1 C2 116.74(13) . . ?
C1 C2 C3 112.39(13) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C2 110.27(14) . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C9 C4 C5 117.47(14) . . ?
C9 C4 C3 125.22(14) . . ?
C5 C4 C3 117.30(13) . . ?
C6 C5 C4 121.91(12) . . ?
C6 C5 N1 119.52(12) . . ?
C4 C5 N1 118.55(12) . . ?
C5 C6 C7 119.19(12) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
O2 C7 C8 124.90(12) . . ?
O2 C7 C6 114.91(12) . . ?
C8 C7 C6 120.17(13) . . ?
C7 C8 C9 119.17(13) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C4 C9 C8 122.05(14) . . ?
C4 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
O2 C10 C11 106.96(12) . . ?
O2 C10 H10A 110.3 . . ?
C11 C10 H10A 110.3 . . ?
O2 C10 H10B 110.3 . . ?
C11 C10 H10B 110.3 . . ?
H10A C10 H10B 108.6 . . ?
C10 C11 C12 112.22(13) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 110.72(12) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
N2 C13 C12 113.78(12) . . ?
N2 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
N2 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
N2 C14 C15 111.95(12) . . ?
N2 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
N2 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
N3 C15 C14 109.34(11) . . ?
N3 C15 H15A 109.8 . . ?
C14 C15 H15A 109.8 . . ?
N3 C15 H15B 109.8 . . ?
C14 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
N2 C16 C17 110.81(11) . . ?
N2 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
N3 C17 C16 110.00(11) . . ?
N3 C17 H17A 109.7 . . ?
C16 C17 H17A 109.7 . . ?
N3 C17 H17B 109.7 . . ?
C16 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C23 C18 C19 117.13(12) . . ?
C23 C18 N3 123.39(12) . . ?
C19 C18 N3 119.44(11) . . ?
C20 C19 C18 120.75(12) . . ?
C20 C19 Cl1 119.36(10) . . ?
C18 C19 Cl1 119.77(10) . . ?
C21 C20 C19 120.90(13) . . ?
C21 C20 Cl2 118.88(11) . . ?
C19 C20 Cl2 120.20(11) . . ?
C22 C21 C20 118.55(13) . . ?
C22 C21 H21 120.7 . . ?
C20 C21 H21 120.7 . . ?
C21 C22 C23 121.24(14) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C22 C23 C18 121.30(13) . . ?
C22 C23 H23 119.4 . . ?
C18 C23 H23 119.4 . . ?
O3 C24 C25 122.58(16) . . ?
O3 C24 C29 117.90(18) . . ?
C25 C24 C29 119.52(16) . . ?
O4 C25 C24 118.71(15) . . ?
O4 C25 C26 120.89(18) . . ?
C24 C25 C26 120.40(18) . . ?
O5 C26 C27 124.33(18) . . ?
O5 C26 C25 115.23(19) . . ?
C27 C26 C25 120.4(2) . . ?
C28 C27 C26 119.00(18) . . ?
C28 C27 H27 120.5 . . ?
C26 C27 H27 120.5 . . ?
C27 C28 C29 121.4(2) . . ?
C27 C28 H28 119.3 . . ?
C29 C28 H28 119.3 . . ?
C24 C29 C28 119.2(2) . . ?
C24 C29 H29 120.4 . . ?
C28 C29 H29 120.4 . . ?
C1 N1 C5 124.15(12) . . ?
C1 N1 H1N 117.2(11) . . ?
C5 N1 H1N 118.1(11) . . ?
C16 N2 C14 108.79(10) . . ?
C16 N2 C13 110.79(11) . . ?
C14 N2 C13 109.33(11) . . ?
C18 N3 C15 116.83(10) . . ?
C18 N3 C17 114.88(10) . . ?
C15 N3 C17 108.77(10) . . ?
C7 O2 C10 118.52(11) . . ?
C24 O3 H3O 115(2) . . ?
C25 O4 H4O 108.1(18) . . ?
C26 O5 H5O 113.7(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -153.19(15) . . . . ?
N1 C1 C2 C3 26.8(2) . . . . ?
C1 C2 C3 C4 -49.6(2) . . . . ?
C2 C3 C4 C9 -141.54(18) . . . . ?
C2 C3 C4 C5 39.3(2) . . . . ?
C9 C4 C5 C6 -2.2(2) . . . . ?
C3 C4 C5 C6 177.04(15) . . . . ?
C9 C4 C5 N1 175.94(14) . . . . ?
C3 C4 C5 N1 -4.8(2) . . . . ?
C4 C5 C6 C7 2.1(2) . . . . ?
N1 C5 C6 C7 -176.07(12) . . . . ?
C5 C6 C7 O2 178.22(12) . . . . ?
C5 C6 C7 C8 -0.5(2) . . . . ?
O2 C7 C8 C9 -179.42(15) . . . . ?
C6 C7 C8 C9 -0.8(2) . . . . ?
C5 C4 C9 C8 0.8(3) . . . . ?
C3 C4 C9 C8 -178.36(18) . . . . ?
C7 C8 C9 C4 0.7(3) . . . . ?
O2 C10 C11 C12 -177.77(12) . . . . ?
C10 C11 C12 C13 -178.13(13) . . . . ?
C11 C12 C13 N2 -166.43(12) . . . . ?
N2 C14 C15 N3 -58.91(16) . . . . ?
N2 C16 C17 N3 60.04(15) . . . . ?
C23 C18 C19 C20 -3.7(2) . . . . ?
N3 C18 C19 C20 178.48(12) . . . . ?
C23 C18 C19 Cl1 172.27(10) . . . . ?
N3 C18 C19 Cl1 -5.57(17) . . . . ?
C18 C19 C20 C21 3.6(2) . . . . ?
Cl1 C19 C20 C21 -172.37(12) . . . . ?
C18 C19 C20 Cl2 -178.10(10) . . . . ?
Cl1 C19 C20 Cl2 5.94(16) . . . . ?
C19 C20 C21 C22 -0.6(2) . . . . ?
Cl2 C20 C21 C22 -178.92(13) . . . . ?
C20 C21 C22 C23 -2.2(3) . . . . ?
C21 C22 C23 C18 2.0(3) . . . . ?
C19 C18 C23 C22 0.9(2) . . . . ?
N3 C18 C23 C22 178.66(14) . . . . ?
O3 C24 C25 O4 1.0(3) . . . . ?
C29 C24 C25 O4 -178.51(16) . . . . ?
O3 C24 C25 C26 -178.48(16) . . . . ?
C29 C24 C25 C26 2.0(2) . . . . ?
O4 C25 C26 O5 -1.8(2) . . . . ?
C24 C25 C26 O5 177.71(16) . . . . ?
O4 C25 C26 C27 178.05(17) . . . . ?
C24 C25 C26 C27 -2.4(3) . . . . ?
O5 C26 C27 C28 -179.08(18) . . . . ?
C25 C26 C27 C28 1.1(3) . . . . ?
C26 C27 C28 C29 0.7(3) . . . . ?
O3 C24 C29 C28 -179.79(17) . . . . ?
C25 C24 C29 C28 -0.2(3) . . . . ?
C27 C28 C29 C24 -1.1(3) . . . . ?
O1 C1 N1 C5 -169.97(12) . . . . ?
C2 C1 N1 C5 10.1(2) . . . . ?
C6 C5 N1 C1 155.63(13) . . . . ?
C4 C5 N1 C1 -22.6(2) . . . . ?
C17 C16 N2 C14 -56.71(15) . . . . ?
C17 C16 N2 C13 -176.92(11) . . . . ?
C15 C14 N2 C16 56.57(16) . . . . ?
C15 C14 N2 C13 177.68(12) . . . . ?
C12 C13 N2 C16 -67.90(15) . . . . ?
C12 C13 N2 C14 172.21(12) . . . . ?
C23 C18 N3 C15 -15.65(19) . . . . ?
C19 C18 N3 C15 162.05(12) . . . . ?
C23 C18 N3 C17 113.55(15) . . . . ?
C19 C18 N3 C17 -68.75(16) . . . . ?
C14 C15 N3 C18 -168.29(12) . . . . ?
C14 C15 N3 C17 59.65(15) . . . . ?
C16 C17 N3 C18 166.04(11) . . . . ?
C16 C17 N3 C15 -60.88(14) . . . . ?
C8 C7 O2 C10 6.5(2) . . . . ?
C6 C7 O2 C10 -172.14(12) . . . . ?
C11 C10 O2 C7 170.83(12) . . . . ?

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.034

