#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:42:58 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180481 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/50/7215035.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7215035
loop_
_publ_author_name
'Nanubolu, Jagadeesh Babu'
'Sridhar, Balasubramanian'
'Babu, V. S. Phani'
'Jagadeesh, Bharatham'
'Ravikumar, Krishnan'
_publ_section_title
;
 Sixth polymorph of aripiprazole - an antipsychotic drug
;
_journal_issue                   14
_journal_name_full               CrystEngComm
_journal_page_first              4677
_journal_paper_doi               10.1039/c2ce25306b
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C23 H27 Cl2 N3 O2'
_chemical_formula_sum            'C23 H27 Cl2 N3 O2'
_chemical_formula_weight         448.38
_chemical_name_common
;7-(4-(4-(2,3-dichlorophenyl)-1-piperazinyl)butoxy)-3,4-
dihydrocarbostyril)
;
_chemical_name_systematic
;7-[4-[4-(2,3-dichlorophenyl)-1-piperazinyl]butoxy]-
3,4-dihydrocarbostyril]
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.396(1)
_cell_angle_beta                 108.921(1)
_cell_angle_gamma                98.847(1)
_cell_formula_units_Z            4
_cell_length_a                   12.2626(7)
_cell_length_b                   13.7872(8)
_cell_length_c                   14.7405(9)
_cell_measurement_reflns_used    8719
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      2.43
_cell_volume                     2246.3(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21716
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.81
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.314
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         7899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0615P)²+0.7519P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1277
_reflns_number_gt                6412
_reflns_number_total             7899
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c2ce25306b.txt
_cod_data_source_block           ab91m
_cod_database_code               7215035
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.36340(19) 0.37796(17) -0.13277(16) 0.0586(5) Uani 1 1 d .
C2 C 0.36797(18) 0.35542(17) -0.04405(16) 0.0548(5) Uani 1 1 d .
C3 C 0.46838(18) 0.32862(16) 0.01444(15) 0.0534(5) Uani 1 1 d .
C4 C 0.5587(2) 0.3239(2) -0.02271(18) 0.0675(6) Uani 1 1 d .
H4 H 0.6273 0.3079 0.0148 0.081 Uiso 1 1 calc R
C5 C 0.5502(2) 0.3419(2) -0.11269(19) 0.0719(7) Uani 1 1 d .
H5 H 0.6114 0.3353 -0.1360 0.086 Uiso 1 1 calc R
C6 C 0.4532(2) 0.36950(19) -0.16871(18) 0.0662(6) Uani 1 1 d .
H6 H 0.4479 0.3822 -0.2295 0.079 Uiso 1 1 calc R
C7 C 0.5662(2) 0.25217(19) 0.14622(17) 0.0607(5) Uani 1 1 d .
H7A H 0.6422 0.3011 0.1768 0.073 Uiso 1 1 calc R
H7B H 0.5709 0.1993 0.0944 0.073 Uiso 1 1 calc R
C8 C 0.5386(2) 0.20594(17) 0.22353(16) 0.0594(5) Uani 1 1 d .
H8A H 0.4660 0.1529 0.1912 0.071 Uiso 1 1 calc R
H8B H 0.6020 0.1746 0.2533 0.071 Uiso 1 1 calc R
C9 C 0.4339(2) 0.33113(17) 0.25554(16) 0.0586(5) Uani 1 1 d .
H9A H 0.4248 0.3819 0.3067 0.070 Uiso 1 1 calc R
H9B H 0.3587 0.2816 0.2209 0.070 Uiso 1 1 calc R
C10 C 0.4672(2) 0.38135(17) 0.18334(16) 0.0597(5) Uani 1 1 d .
H10A H 0.4086 0.4181 0.1561 0.072 Uiso 1 1 calc R
H10B H 0.5436 0.4295 0.2172 0.072 Uiso 1 1 calc R
C11 C 0.4927(2) 0.23375(18) 0.37239(16) 0.0617(6) Uani 1 1 d .
H11A H 0.4248 0.1768 0.3359 0.074 Uiso 1 1 calc R
H11B H 0.4685 0.2829 0.4141 0.074 Uiso 1 1 calc R
C12 C 0.5902(2) 0.19619(19) 0.43849(16) 0.0616(6) Uani 1 1 d .
H12A H 0.6632 0.2489 0.4665 0.074 Uiso 1 1 calc R
H12B H 0.6038 0.1370 0.3996 0.074 Uiso 1 1 calc R
C13 C 0.5556(2) 0.1684(2) 0.52177(17) 0.0684(6) Uani 1 1 d .
H13A H 0.5357 0.2265 0.5564 0.082 Uiso 1 1 calc R
H13B H 0.4852 0.1130 0.4929 0.082 Uiso 1 1 calc R
C14 C 0.6501(2) 0.1373(2) 0.59540(17) 0.0670(6) Uani 1 1 d .
H14A H 0.6688 0.0770 0.5634 0.080 Uiso 1 1 calc R
H14B H 0.7217 0.1915 0.6258 0.080 Uiso 1 1 calc R
C15 C 0.67050(19) 0.08410(18) 0.74452(16) 0.0587(5) Uani 1 1 d .
C16 C 0.7784(2) 0.0614(2) 0.75357(17) 0.0675(6) Uani 1 1 d .
H16 H 0.8125 0.0702 0.7070 0.081 Uiso 1 1 calc R
C17 C 0.8350(2) 0.0255(2) 0.83238(17) 0.0693(6) Uani 1 1 d .
H17 H 0.9079 0.0103 0.8381 0.083 Uiso 1 1 calc R
C18 C 0.78826(18) 0.01100(18) 0.90354(16) 0.0591(5) Uani 1 1 d .
C19 C 0.67970(17) 0.03542(15) 0.89309(14) 0.0483(5) Uani 1 1 d .
C20 C 0.62103(19) 0.07185(16) 0.81526(15) 0.0547(5) Uani 1 1 d .
H20 H 0.5488 0.0882 0.8100 0.066 Uiso 1 1 calc R
C21 C 0.8482(2) -0.0232(3) 0.9931(2) 0.0862(8) Uani 1 1 d .
H21A H 0.8947 -0.0697 0.9762 0.103 Uiso 1 1 calc R
H21B H 0.9025 0.0354 1.0449 0.103 Uiso 1 1 calc R
C22 C 0.7675(2) -0.0731(2) 1.0319(2) 0.0795(7) Uani 1 1 d .
H22A H 0.8124 -0.0726 1.0997 0.095 Uiso 1 1 calc R
H22B H 0.7379 -0.1437 0.9934 0.095 Uiso 1 1 calc R
C23 C 0.66471(19) -0.02968(18) 1.03223(15) 0.0586(5) Uani 1 1 d .
Cl1 Cl 0.24325(6) 0.41769(6) -0.20122(5) 0.0872(2) Uani 1 1 d .
Cl2 Cl 0.24468(5) 0.35402(6) -0.01098(5) 0.0762(2) Uani 1 1 d .
N1 N 0.47308(15) 0.30280(13) 0.10299(12) 0.0537(4) Uani 1 1 d .
N2 N 0.52515(15) 0.28076(13) 0.30136(12) 0.0542(4) Uani 1 1 d .
N3 N 0.62805(16) 0.02223(14) 0.96379(13) 0.0545(4) Uani 1 1 d .
H3N H 0.560(2) 0.0377(17) 0.9532(16) 0.059(6) Uiso 1 1 d .
O1 O 0.60308(15) 0.11674(16) 0.66837(13) 0.0815(5) Uani 1 1 d .
O2 O 0.61067(15) -0.04405(15) 1.08725(12) 0.0777(5) Uani 1 1 d .
C1' C 1.1272(2) 0.14487(18) 0.64511(18) 0.0632(6) Uani 1 1 d .
C2' C 1.0702(2) 0.16285(16) 0.55445(17) 0.0593(5) Uani 1 1 d .
C3' C 1.1255(2) 0.16269(17) 0.48457(17) 0.0589(5) Uani 1 1 d .
C4' C 1.2370(2) 0.1423(2) 0.5106(2) 0.0814(8) Uani 1 1 d .
H4' H 1.2757 0.1409 0.4657 0.098 Uiso 1 1 calc R
C5' C 1.2922(3) 0.1241(3) 0.6009(2) 0.0946(9) Uani 1 1 d .
H5' H 1.3674 0.1111 0.6161 0.113 Uiso 1 1 calc R
C6' C 1.2375(2) 0.1250(2) 0.6690(2) 0.0814(8) Uani 1 1 d .
H6' H 1.2746 0.1123 0.7299 0.098 Uiso 1 1 calc R
C7' C 1.1468(2) 0.2233(2) 0.34345(18) 0.0668(6) Uani 1 1 d .
H7C H 1.1648 0.1648 0.3075 0.080 Uiso 1 1 calc R
H7D H 1.2209 0.2684 0.3906 0.080 Uiso 1 1 calc R
C8' C 1.0822(2) 0.27838(19) 0.27143(17) 0.0664(6) Uani 1 1 d .
H8C H 1.0689 0.3390 0.3084 0.080 Uiso 1 1 calc R
H8D H 1.1313 0.2997 0.2357 0.080 Uiso 1 1 calc R
C9' C 0.8971(2) 0.17840(19) 0.25462(18) 0.0675(6) Uani 1 1 d .
H9C H 0.8223 0.1341 0.2078 0.081 Uiso 1 1 calc R
H9D H 0.8800 0.2360 0.2927 0.081 Uiso 1 1 calc R
C10' C 0.9615(2) 0.12139(18) 0.32367(18) 0.0671(6) Uani 1 1 d .
H10C H 0.9120 0.0959 0.3575 0.081 Uiso 1 1 calc R
H10D H 0.9790 0.0638 0.2860 0.081 Uiso 1 1 calc R
C11' C 0.9041(2) 0.2686(2) 0.13335(18) 0.0669(6) Uani 1 1 d .
H11C H 0.8974 0.3308 0.1731 0.080 Uiso 1 1 calc R
H11D H 0.8245 0.2270 0.0958 0.080 Uiso 1 1 calc R
C12' C 0.9594(2) 0.2956(2) 0.06079(18) 0.0684(6) Uani 1 1 d .
H12C H 0.9770 0.2358 0.0267 0.082 Uiso 1 1 calc R
H12D H 1.0332 0.3468 0.0965 0.082 Uiso 1 1 calc R
C13' C 0.8743(2) 0.3362(2) -0.01453(18) 0.0687(6) Uani 1 1 d .
H13C H 0.7998 0.2856 -0.0473 0.082 Uiso 1 1 calc R
H13D H 0.8587 0.3966 0.0205 0.082 Uiso 1 1 calc R
C14' C 0.9190(2) 0.3623(2) -0.09208(18) 0.0678(6) Uani 1 1 d .
H14C H 0.9936 0.4129 -0.0612 0.081 Uiso 1 1 calc R
H14D H 0.9312 0.3021 -0.1307 0.081 Uiso 1 1 calc R
C15' C 0.84084(19) 0.41727(18) -0.23978(17) 0.0600(5) Uani 1 1 d .
C16' C 0.9387(2) 0.4099(2) -0.26541(19) 0.0694(6) Uani 1 1 d .
H16' H 1.0048 0.3957 -0.2221 0.083 Uiso 1 1 calc R
C17' C 0.9374(2) 0.4238(2) -0.35582(19) 0.0696(6) Uani 1 1 d .
H17' H 1.0035 0.4184 -0.3726 0.084 Uiso 1 1 calc R
C18' C 0.84159(19) 0.44532(18) -0.42228(17) 0.0601(5) Uani 1 1 d .
C19' C 0.74611(18) 0.45701(16) -0.39261(15) 0.0522(5) Uani 1 1 d .
C20' C 0.74507(19) 0.44243(17) -0.30303(16) 0.0566(5) Uani 1 1 d .
H20' H 0.6800 0.4495 -0.2851 0.068 Uiso 1 1 calc R
C21' C 0.8284(2) 0.4516(2) -0.52582(19) 0.0738(7) Uani 1 1 d .
H21C H 0.7840 0.3866 -0.5728 0.089 Uiso 1 1 calc R
H21D H 0.9062 0.4667 -0.5302 0.089 Uiso 1 1 calc R
C22' C 0.7650(2) 0.5333(2) -0.55235(19) 0.0757(7) Uani 1 1 d .
H22C H 0.8171 0.5995 -0.5145 0.091 Uiso 1 1 calc R
H22D H 0.7468 0.5291 -0.6224 0.091 Uiso 1 1 calc R
C23' C 0.6518(2) 0.52409(18) -0.53174(16) 0.0625(6) Uani 1 1 d .
Cl1' Cl 1.06158(7) 0.15258(6) 0.73352(5) 0.0840(2) Uani 1 1 d .
Cl2' Cl 0.93312(7) 0.19071(7) 0.53007(6) 0.0964(3) Uani 1 1 d .
N1' N 1.07163(16) 0.18992(14) 0.39643(13) 0.0589(4) Uani 1 1 d .
N2' N 0.96860(16) 0.21431(14) 0.20033(13) 0.0601(5) Uani 1 1 d .
N3' N 0.64901(17) 0.48355(15) -0.45658(13) 0.0591(5) Uani 1 1 d .
H3' H 0.580(2) 0.4743(18) -0.4452(18) 0.073(7) Uiso 1 1 d .
O1' O 0.83034(15) 0.40137(15) -0.15429(13) 0.0774(5) Uani 1 1 d .
O2' O 0.56689(15) 0.55318(14) -0.57969(12) 0.0737(5) Uani 1 1 d .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 121.5(2) ?
C6 C1 Cl1 118.28(17) ?
C2 C1 Cl1 120.19(17) ?
C1 C2 C3 120.29(19) ?
C1 C2 Cl2 118.69(16) ?
C3 C2 Cl2 120.92(16) ?
C4 C3 C2 116.51(19) ?
C4 C3 N1 122.38(19) ?
C2 C3 N1 121.02(18) ?
C5 C4 C3 122.3(2) ?
C5 C4 H4 118.9 ?
C3 C4 H4 118.9 ?
C6 C5 C4 121.0(2) ?
C6 C5 H5 119.5 ?
C4 C5 H5 119.5 ?
C5 C6 C1 118.2(2) ?
C5 C6 H6 120.9 ?
C1 C6 H6 120.9 ?
N1 C7 C8 109.69(17) ?
N1 C7 H7A 109.7 ?
C8 C7 H7A 109.7 ?
N1 C7 H7B 109.7 ?
C8 C7 H7B 109.7 ?
H7A C7 H7B 108.2 ?
N2 C8 C7 112.50(18) ?
N2 C8 H8A 109.1 ?
C7 C8 H8A 109.1 ?
N2 C8 H8B 109.1 ?
C7 C8 H8B 109.1 ?
H8A C8 H8B 107.8 ?
N2 C9 C10 110.28(18) ?
N2 C9 H9A 109.6 ?
C10 C9 H9A 109.6 ?
N2 C9 H9B 109.6 ?
C10 C9 H9B 109.6 ?
H9A C9 H9B 108.1 ?
N1 C10 C9 108.93(17) ?
N1 C10 H10A 109.9 ?
C9 C10 H10A 109.9 ?
N1 C10 H10B 109.9 ?
C9 C10 H10B 109.9 ?
H10A C10 H10B 108.3 ?
N2 C11 C12 114.59(18) ?
N2 C11 H11A 108.6 ?
C12 C11 H11A 108.6 ?
N2 C11 H11B 108.6 ?
C12 C11 H11B 108.6 ?
H11A C11 H11B 107.6 ?
C11 C12 C13 109.89(19) ?
C11 C12 H12A 109.7 ?
C13 C12 H12A 109.7 ?
C11 C12 H12B 109.7 ?
C13 C12 H12B 109.7 ?
H12A C12 H12B 108.2 ?
C14 C13 C12 114.0(2) ?
C14 C13 H13A 108.8 ?
C12 C13 H13A 108.8 ?
C14 C13 H13B 108.8 ?
C12 C13 H13B 108.8 ?
H13A C13 H13B 107.7 ?
O1 C14 C13 105.91(18) ?
O1 C14 H14A 110.6 ?
C13 C14 H14A 110.6 ?
O1 C14 H14B 110.6 ?
C13 C14 H14B 110.6 ?
H14A C14 H14B 108.7 ?
O1 C15 C16 125.13(19) ?
O1 C15 C20 114.84(19) ?
C16 C15 C20 120.02(19) ?
C17 C16 C15 119.1(2) ?
C17 C16 H16 120.5 ?
C15 C16 H16 120.5 ?
C16 C17 C18 122.7(2) ?
C16 C17 H17 118.6 ?
C18 C17 H17 118.6 ?
C17 C18 C19 117.0(2) ?
C17 C18 C21 125.1(2) ?
C19 C18 C21 117.86(19) ?
C20 C19 C18 121.67(18) ?
C20 C19 N3 119.00(18) ?
C18 C19 N3 119.33(18) ?
C19 C20 C15 119.50(19) ?
C19 C20 H20 120.3 ?
C15 C20 H20 120.3 ?
C22 C21 C18 114.0(2) ?
C22 C21 H21A 108.7 ?
C18 C21 H21A 108.7 ?
C22 C21 H21B 108.7 ?
C18 C21 H21B 108.7 ?
H21A C21 H21B 107.6 ?
C21 C22 C23 116.8(2) ?
C21 C22 H22A 108.1 ?
C23 C22 H22A 108.1 ?
C21 C22 H22B 108.1 ?
C23 C22 H22B 108.1 ?
H22A C22 H22B 107.3 ?
O2 C23 N3 121.1(2) ?
O2 C23 C22 122.7(2) ?
N3 C23 C22 116.11(19) ?
C3 N1 C7 117.32(17) y
C3 N1 C10 117.59(17) ?
C7 N1 C10 108.38(17) ?
C8 N2 C9 108.76(16) ?
C8 N2 C11 111.62(17) ?
C9 N2 C11 109.72(17) y
C23 N3 C19 124.52(19) y
C23 N3 H3N 118.6(15) ?
C19 N3 H3N 115.5(15) ?
C15 O1 C14 118.66(17) ?
C6' C1' C2' 121.5(2) ?
C6' C1' Cl1' 118.47(19) ?
C2' C1' Cl1' 119.96(19) ?
C1' C2' C3' 120.5(2) ?
C1' C2' Cl2' 119.30(18) ?
C3' C2' Cl2' 120.16(17) ?
C4' C3' C2' 116.8(2) ?
C4' C3' N1' 122.9(2) ?
C2' C3' N1' 120.1(2) ?
C5' C4' C3' 121.9(2) ?
C5' C4' H4' 119.0 ?
C3' C4' H4' 119.0 ?
C6' C5' C4' 120.8(3) ?
C6' C5' H5' 119.6 ?
C4' C5' H5' 119.6 ?
C1' C6' C5' 118.5(2) ?
C1' C6' H6' 120.8 ?
C5' C6' H6' 120.8 ?
N1' C7' C8' 109.12(19) ?
N1' C7' H7C 109.9 ?
C8' C7' H7C 109.9 ?
N1' C7' H7D 109.9 ?
C8' C7' H7D 109.9 ?
H7C C7' H7D 108.3 ?
N2' C8' C7' 111.91(19) ?
N2' C8' H8C 109.2 ?
C7' C8' H8C 109.2 ?
N2' C8' H8D 109.2 ?
C7' C8' H8D 109.2 ?
H8C C8' H8D 107.9 ?
N2' C9' C10' 110.6(2) ?
N2' C9' H9C 109.5 ?
C10' C9' H9C 109.5 ?
N2' C9' H9D 109.5 ?
C10' C9' H9D 109.5 ?
H9C C9' H9D 108.1 ?
N1' C10' C9' 109.13(18) ?
N1' C10' H10C 109.9 ?
C9' C10' H10C 109.9 ?
N1' C10' H10D 109.9 ?
C9' C10' H10D 109.9 ?
H10C C10' H10D 108.3 ?
N2' C11' C12' 115.2(2) ?
N2' C11' H11C 108.5 ?
C12' C11' H11C 108.5 ?
N2' C11' H11D 108.5 ?
C12' C11' H11D 108.5 ?
H11C C11' H11D 107.5 ?
C11' C12' C13' 109.6(2) ?
C11' C12' H12C 109.7 ?
C13' C12' H12C 109.7 ?
C11' C12' H12D 109.7 ?
C13' C12' H12D 109.7 ?
H12C C12' H12D 108.2 ?
C14' C13' C12' 114.0(2) ?
C14' C13' H13C 108.8 ?
C12' C13' H13C 108.8 ?
C14' C13' H13D 108.8 ?
C12' C13' H13D 108.8 ?
H13C C13' H13D 107.6 ?
O1' C14' C13' 106.54(19) ?
O1' C14' H14C 110.4 ?
C13' C14' H14C 110.4 ?
O1' C14' H14D 110.4 ?
C13' C14' H14D 110.4 ?
H14C C14' H14D 108.6 ?
O1' C15' C16' 124.5(2) ?
O1' C15' C20' 115.73(19) ?
C16' C15' C20' 119.8(2) ?
C17' C16' C15' 119.3(2) ?
C17' C16' H16' 120.3 ?
C15' C16' H16' 120.3 ?
C16' C17' C18' 122.4(2) ?
C16' C17' H17' 118.8 ?
C18' C17' H17' 118.8 ?
C17' C18' C19' 117.1(2) ?
C17' C18' C21' 125.6(2) ?
C19' C18' C21' 117.2(2) ?
C20' C19' C18' 121.4(2) ?
C20' C19' N3' 119.88(19) ?
C18' C19' N3' 118.73(19) ?
C19' C20' C15' 119.9(2) ?
C19' C20' H20' 120.0 ?
C15' C20' H20' 120.0 ?
C18' C21' C22' 110.7(2) ?
C18' C21' H21C 109.5 ?
C22' C21' H21C 109.5 ?
C18' C21' H21D 109.5 ?
C22' C21' H21D 109.5 ?
H21C C21' H21D 108.1 ?
C23' C22' C21' 112.4(2) ?
C23' C22' H22C 109.1 ?
C21' C22' H22C 109.1 ?
C23' C22' H22D 109.1 ?
C21' C22' H22D 109.1 ?
H22C C22' H22D 107.9 ?
O2' C23' N3' 121.3(2) ?
O2' C23' C22' 122.3(2) ?
N3' C23' C22' 116.4(2) ?
C3' N1' C10' 117.57(18) ?
C3' N1' C7' 118.05(18) y
C10' N1' C7' 108.57(18) ?
C11' N2' C8' 111.98(18) ?
C11' N2' C9' 109.66(18) y
C8' N2' C9' 109.05(17) ?
C23' N3' C19' 124.6(2) y
C23' N3' H3' 117.6(16) ?
C19' N3' H3' 117.7(16) ?
C15' O1' C14' 118.46(18) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 1.378(3) ?
C1 C2 1.389(3) ?
C1 Cl1 1.730(2) ?
C2 C3 1.405(3) ?
C2 Cl2 1.731(2) ?
C3 C4 1.390(3) ?
C3 N1 1.405(3) y
C4 C5 1.371(3) ?
C4 H4 0.9300 ?
C5 C6 1.367(3) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 N1 1.465(3) y
C7 C8 1.513(3) ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 N2 1.454(3) y
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C9 N2 1.457(3) y
C9 C10 1.505(3) ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 N1 1.467(3) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C11 N2 1.461(3) ?
C11 C12 1.511(3) ?
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
C12 C13 1.519(3) ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C13 C14 1.492(3) ?
C13 H13A 0.9700 ?
C13 H13B 0.9700 ?
C14 O1 1.429(2) ?
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
C15 O1 1.363(3) ?
C15 C16 1.377(3) ?
C15 C20 1.390(3) ?
C16 C17 1.373(3) ?
C16 H16 0.9300 ?
C17 C18 1.381(3) ?
C17 H17 0.9300 ?
C18 C19 1.391(3) ?
C18 C21 1.493(3) ?
C19 C20 1.375(3) ?
C19 N3 1.410(2) ?
C20 H20 0.9300 ?
C21 C22 1.446(4) ?
C21 H21A 0.9700 ?
C21 H21B 0.9700 ?
C22 C23 1.478(3) ?
C22 H22A 0.9700 ?
C22 H22B 0.9700 ?
C23 O2 1.228(3) ?
C23 N3 1.350(3) ?
N3 H3N 0.87(2) ?
C1' C6' 1.368(4) ?
C1' C2' 1.384(3) ?
C1' Cl1' 1.735(2) ?
C2' C3' 1.405(3) ?
C2' Cl2' 1.722(2) ?
C3' C4' 1.384(3) ?
C3' N1' 1.406(3) y
C4' C5' 1.377(4) ?
C4' H4' 0.9300 ?
C5' C6' 1.375(4) ?
C5' H5' 0.9300 ?
C6' H6' 0.9300 ?
C7' N1' 1.466(3) y
C7' C8' 1.513(3) ?
C7' H7C 0.9700 ?
C7' H7D 0.9700 ?
C8' N2' 1.459(3) y
C8' H8C 0.9700 ?
C8' H8D 0.9700 ?
C9' N2' 1.461(3) y
C9' C10' 1.505(3) ?
C9' H9C 0.9700 ?
C9' H9D 0.9700 ?
C10' N1' 1.461(3) ?
C10' H10C 0.9700 ?
C10' H10D 0.9700 ?
C11' N2' 1.458(3) ?
C11' C12' 1.514(3) ?
C11' H11C 0.9700 ?
C11' H11D 0.9700 ?
C12' C13' 1.519(3) ?
C12' H12C 0.9700 ?
C12' H12D 0.9700 ?
C13' C14' 1.497(3) ?
C13' H13C 0.9700 ?
C13' H13D 0.9700 ?
C14' O1' 1.429(3) ?
C14' H14C 0.9700 ?
C14' H14D 0.9700 ?
C15' O1' 1.363(3) ?
C15' C16' 1.382(3) ?
C15' C20' 1.383(3) ?
C16' C17' 1.379(3) ?
C16' H16' 0.9300 ?
C17' C18' 1.380(3) ?
C17' H17' 0.9300 ?
C18' C19' 1.397(3) ?
C18' C21' 1.503(3) ?
C19' C20' 1.378(3) ?
C19' N3' 1.408(3) ?
C20' H20' 0.9300 ?
C21' C22' 1.507(4) ?
C21' H21C 0.9700 ?
C21' H21D 0.9700 ?
C22' C23' 1.506(3) ?
C22' H22C 0.9700 ?
C22' H22D 0.9700 ?
C23' O2' 1.228(3) ?
C23' N3' 1.343(3) ?
N3' H3' 0.91(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3N O2 0.87(2) 2.00(2) 2.856(3) 168(2) 2_657
N3' H3' O2' 0.91(3) 1.95(3) 2.857(3) 177(2) 2_664
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_publ_flag
C6 C1 C2 C3 3.6(4) ?
Cl1 C1 C2 C3 -176.45(17) ?
C6 C1 C2 Cl2 -172.80(19) ?
Cl1 C1 C2 Cl2 7.2(3) ?
C1 C2 C3 C4 -1.5(3) ?
Cl2 C2 C3 C4 174.76(18) ?
C1 C2 C3 N1 -178.2(2) ?
Cl2 C2 C3 N1 -1.9(3) ?
C2 C3 C4 C5 -1.5(4) ?
N1 C3 C4 C5 175.1(2) ?
C3 C4 C5 C6 2.5(4) ?
C4 C5 C6 C1 -0.5(4) ?
C2 C1 C6 C5 -2.5(4) ?
Cl1 C1 C6 C5 177.5(2) ?
N1 C7 C8 N2 -56.9(3) ?
N2 C9 C10 N1 62.9(2) ?
N2 C11 C12 C13 168.87(19) y
C11 C12 C13 C14 -175.9(2) ?
C12 C13 C14 O1 178.6(2) y
O1 C15 C16 C17 -177.6(2) ?
C20 C15 C16 C17 0.8(4) ?
C15 C16 C17 C18 0.0(4) ?
C16 C17 C18 C19 -0.6(4) ?
C16 C17 C18 C21 -177.1(3) ?
C17 C18 C19 C20 0.3(3) ?
C21 C18 C19 C20 177.1(2) ?
C17 C18 C19 N3 -179.9(2) ?
C21 C18 C19 N3 -3.1(3) ?
C18 C19 C20 C15 0.5(3) ?
N3 C19 C20 C15 -179.3(2) ?
O1 C15 C20 C19 177.5(2) ?
C16 C15 C20 C19 -1.0(4) ?
C17 C18 C21 C22 -155.1(3) ?
C19 C18 C21 C22 28.4(4) ?
C18 C21 C22 C23 -39.7(4) ?
C21 C22 C23 O2 -158.2(3) ?
C21 C22 C23 N3 25.7(4) ?
C4 C3 N1 C7 -11.2(3) ?
C2 C3 N1 C7 165.3(2) ?
C4 C3 N1 C10 120.9(2) ?
C2 C3 N1 C10 -62.6(3) ?
C8 C7 N1 C3 -165.16(19) ?
C8 C7 N1 C10 58.7(2) ?
C9 C10 N1 C3 161.82(18) ?
C9 C10 N1 C7 -62.2(2) ?
C7 C8 N2 C9 55.9(2) ?
C7 C8 N2 C11 177.11(18) ?
C10 C9 N2 C8 -58.5(2) ?
C10 C9 N2 C11 179.10(18) ?
C12 C11 N2 C8 70.2(2) ?
C12 C11 N2 C9 -169.12(19) ?
O2 C23 N3 C19 -175.0(2) ?
C22 C23 N3 C19 1.1(3) ?
C20 C19 N3 C23 167.2(2) ?
C18 C19 N3 C23 -12.5(3) ?
C16 C15 O1 C14 -5.3(4) ?
C20 C15 O1 C14 176.3(2) ?
C13 C14 O1 C15 178.5(2) ?
C6' C1' C2' C3' -1.0(4) ?
Cl1' C1' C2' C3' 176.27(18) ?
C6' C1' C2' Cl2' -178.3(2) ?
Cl1' C1' C2' Cl2' -1.0(3) ?
C1' C2' C3' C4' 1.0(3) ?
Cl2' C2' C3' C4' 178.3(2) ?
C1' C2' C3' N1' -174.3(2) ?
Cl2' C2' C3' N1' 3.0(3) ?
C2' C3' C4' C5' -0.7(4) ?
N1' C3' C4' C5' 174.5(3) ?
C3' C4' C5' C6' 0.4(5) ?
C2' C1' C6' C5' 0.7(4) ?
Cl1' C1' C6' C5' -176.6(2) ?
C4' C5' C6' C1' -0.4(5) ?
N1' C7' C8' N2' -58.1(3) ?
N2' C9' C10' N1' 61.5(3) ?
N2' C11' C12' C13' 171.0(2) y
C11' C12' C13' C14' -178.1(2) ?
C12' C13' C14' O1' -178.5(2) y
O1' C15' C16' C17' 177.5(2) ?
C20' C15' C16' C17' -2.6(4) ?
C15' C16' C17' C18' 0.3(4) ?
C16' C17' C18' C19' 2.6(4) ?
C16' C17' C18' C21' -173.8(3) ?
C17' C18' C19' C20' -3.3(3) ?
C21' C18' C19' C20' 173.5(2) ?
C17' C18' C19' N3' 177.2(2) ?
C21' C18' C19' N3' -6.1(3) ?
C18' C19' C20' C15' 1.1(3) ?
N3' C19' C20' C15' -179.4(2) ?
O1' C15' C20' C19' -178.1(2) ?
C16' C15' C20' C19' 2.0(4) ?
C17' C18' C21' C22' -144.5(2) ?
C19' C18' C21' C22' 39.1(3) ?
C18' C21' C22' C23' -50.2(3) ?
C21' C22' C23' O2' -151.2(2) ?
C21' C22' C23' N3' 29.9(3) ?
C4' C3' N1' C10' 117.2(3) ?
C2' C3' N1' C10' -67.8(3) ?
C4' C3' N1' C7' -16.0(3) ?
C2' C3' N1' C7' 159.0(2) ?
C9' C10' N1' C3' 160.5(2) ?
C9' C10' N1' C7' -62.2(3) ?
C8' C7' N1' C3' -162.82(19) ?
C8' C7' N1' C10' 60.1(2) ?
C12' C11' N2' C8' 68.0(3) ?
C12' C11' N2' C9' -170.8(2) ?
C7' C8' N2' C11' 177.8(2) ?
C7' C8' N2' C9' 56.2(3) ?
C10' C9' N2' C11' 179.54(19) ?
C10' C9' N2' C8' -57.5(3) ?
O2' C23' N3' C19' -174.0(2) ?
C22' C23' N3' C19' 5.0(3) ?
C20' C19' N3' C23' 162.4(2) ?
C18' C19' N3' C23' -18.1(3) ?
C16' C15' O1' C14' -8.2(4) ?
C20' C15' O1' C14' 171.9(2) ?
C13' C14' O1' C15' -170.6(2) ?
