#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:18:17 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179659 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/12/4511235.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_4511235
loop_
_publ_author_name
'Aitipamula, Srinivasulu'
'Wong, Annie B. H.'
'Chow, Pui Shan'
'Tan, Reginald B. H.'
_publ_section_title
;
 Pharmaceutical Salts of Haloperidol with Some Carboxylic Acids and
 Artificial Sweeteners: Hydrate Formation, Polymorphism, and
 Physicochemical Properties
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2542
_journal_paper_doi               10.1021/cg500245e
_journal_volume                  14
_journal_year                    2014
_chemical_formula_sum            'C44 H52 Cl2 F2 N2 O10'
_chemical_formula_weight         877.78
_chemical_name_common            'Haloperidol-oxalic acid dihydrate'
_chemical_name_systematic        'Haloperidol-oxalic acid hydrate'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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                114.00(3)
_cell_angle_beta                 99.25(3)
_cell_angle_gamma                90.72(3)
_cell_formula_units_Z            2
_cell_length_a                   11.961(2)
_cell_length_b                   12.954(3)
_cell_length_c                   14.825(3)
_cell_measurement_reflns_used    5904
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      31.1172
_cell_measurement_theta_min      2.3379
_cell_volume                     2063.4(9)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29670
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.9556
_exptl_absorpt_correction_T_min  0.9242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'R. H. Blessing, Acta Cryst. 1995 A51, 33-38'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             924
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     573
_refine_ls_number_reflns         10070
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0383
_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)+(0.0461P)²+0.9120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.0972
_reflns_number_gt                9789
_reflns_number_total             10070
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg500245e_si_003.cif
_cod_data_source_block           Hal-OA
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4511235
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
Cl1 Cl 0.26162(3) 1.10425(3) 1.01255(2) 0.02864(8) Uani 1 1 d .
Cl2 Cl 0.44315(3) 0.64719(3) 0.05971(2) 0.03576(9) Uani 1 1 d .
O1 O 0.02188(7) 0.84887(7) 0.52450(6) 0.01833(16) Uani 1 1 d .
F2 F 1.55885(7) 0.75271(8) 0.79242(6) 0.03353(19) Uani 1 1 d .
O6 O -0.03511(7) 0.64085(7) 0.53316(6) 0.01906(16) Uani 1 1 d .
O5 O 0.06675(8) 0.53590(7) 0.41880(6) 0.02147(17) Uani 1 1 d .
O3 O 0.52008(7) 0.68809(7) 0.52528(6) 0.01927(17) Uani 1 1 d .
F1 F 0.15668(7) 0.25130(7) -0.34003(6) 0.03032(18) Uani 1 1 d .
O7 O 0.44260(7) 0.88734(7) 0.51964(7) 0.02158(17) Uani 1 1 d .
O4 O 1.09746(8) 0.82936(8) 0.95355(6) 0.02472(18) Uani 1 1 d .
N1 N 0.23104(8) 0.82332(8) 0.37173(7) 0.01585(18) Uani 1 1 d .
O2 O 0.17932(10) 0.51169(8) 0.12543(7) 0.0319(2) Uani 1 1 d .
N2 N 0.78456(8) 0.64274(8) 0.63647(7) 0.01560(18) Uani 1 1 d .
O8 O 0.59713(8) 1.00792(8) 0.60474(7) 0.02408(18) Uani 1 1 d .
C28 C 0.61563(9) 0.66379(9) 0.47378(8) 0.0159(2) Uani 1 1 d .
C43 C 0.00956(9) 0.55106(9) 0.48549(8) 0.01489(19) Uani 1 1 d .
C14 C 0.11213(10) 1.01534(10) 0.83701(9) 0.0200(2) Uani 1 1 d .
H14 H 0.0541 1.0304 0.8765 0.024 Uiso 1 1 calc R
C31 C 0.57796(9) 0.65799(10) 0.36782(8) 0.0177(2) Uani 1 1 d .
C10 C 0.16913(9) 0.94182(9) 0.67349(8) 0.0153(2) Uani 1 1 d .
C26 C 0.75387(10) 0.75591(9) 0.63967(8) 0.0174(2) Uani 1 1 d .
H26A H 0.8204 0.8122 0.6751 0.021 Uiso 1 1 calc R
H26B H 0.6915 0.7811 0.6782 0.021 Uiso 1 1 calc R
C22 C 1.11436(10) 0.77820(9) 0.86790(8) 0.0179(2) Uani 1 1 d .
C44 C 0.51139(9) 0.96991(9) 0.53634(9) 0.0180(2) Uani 1 1 d .
C7 C 0.13991(9) 0.88410(9) 0.55886(8) 0.0152(2) Uani 1 1 d .
C8 C 0.21075(9) 0.78200(9) 0.51871(8) 0.0158(2) Uani 1 1 d .
H8A H 0.2915 0.8059 0.5507 0.019 Uiso 1 1 calc R
H8B H 0.1850 0.7220 0.5379 0.019 Uiso 1 1 calc R
C9 C 0.20131(10) 0.73316(9) 0.40534(8) 0.0180(2) Uani 1 1 d .
H9A H 0.2532 0.6722 0.3842 0.022 Uiso 1 1 calc R
H9B H 0.1227 0.6994 0.3728 0.022 Uiso 1 1 calc R
C15 C 0.08475(10) 0.96429(10) 0.73219(9) 0.0181(2) Uani 1 1 d .
H15 H 0.0072 0.9445 0.7004 0.022 Uiso 1 1 calc R
C27 C 0.71654(9) 0.75228(9) 0.53514(8) 0.0170(2) Uani 1 1 d .
H27A H 0.7813 0.7343 0.4989 0.020 Uiso 1 1 calc R
H27B H 0.6948 0.8281 0.5414 0.020 Uiso 1 1 calc R
C5 C 0.15249(10) 0.91628(9) 0.40292(8) 0.0170(2) Uani 1 1 d .
H5A H 0.0728 0.8846 0.3728 0.020 Uiso 1 1 calc R
H5B H 0.1706 0.9742 0.3786 0.020 Uiso 1 1 calc R
C13 C 0.22570(10) 1.04352(10) 0.88217(8) 0.0194(2) Uani 1 1 d .
C6 C 0.16616(9) 0.97050(9) 0.51658(8) 0.0164(2) Uani 1 1 d .
H6A H 0.1144 1.0317 0.5367 0.020 Uiso 1 1 calc R
H6B H 0.2451 1.0051 0.5459 0.020 Uiso 1 1 calc R
C25 C 0.81008(10) 0.64224(10) 0.73926(8) 0.0188(2) Uani 1 1 d .
H25A H 0.8329 0.5664 0.7317 0.023 Uiso 1 1 calc R
H25B H 0.7392 0.6536 0.7673 0.023 Uiso 1 1 calc R
C11 C 0.28277(9) 0.97476(9) 0.72196(8) 0.0167(2) Uani 1 1 d .
H11 H 0.3410 0.9626 0.6830 0.020 Uiso 1 1 calc R
C29 C 0.65154(10) 0.54968(9) 0.47093(9) 0.0181(2) Uani 1 1 d .
H29A H 0.5870 0.4912 0.4347 0.022 Uiso 1 1 calc R
H29B H 0.7150 0.5273 0.4333 0.022 Uiso 1 1 calc R
C23 C 1.01715(10) 0.71825(10) 0.78138(8) 0.0181(2) Uani 1 1 d .
H23A H 1.0291 0.6367 0.7493 0.022 Uiso 1 1 calc R
H23B H 1.0172 0.7496 0.7306 0.022 Uiso 1 1 calc R
C32 C 0.59040(11) 0.75313(10) 0.34748(9) 0.0219(2) Uani 1 1 d .
H32 H 0.6283 0.8215 0.3992 0.026 Uiso 1 1 calc R
C24 C 0.90205(10) 0.73068(10) 0.81425(8) 0.0197(2) Uani 1 1 d .
H24A H 0.9098 0.7249 0.8795 0.024 Uiso 1 1 calc R
H24B H 0.8784 0.8070 0.8244 0.024 Uiso 1 1 calc R
C4 C 0.23447(10) 0.77465(10) 0.26114(8) 0.0191(2) Uani 1 1 d .
H4A H 0.2825 0.7101 0.2450 0.023 Uiso 1 1 calc R
H4B H 0.2706 0.8332 0.2456 0.023 Uiso 1 1 calc R
C12 C 0.31158(10) 1.02491(9) 0.82613(8) 0.0181(2) Uani 1 1 d .
H12 H 0.3888 1.0461 0.8584 0.022 Uiso 1 1 calc R
C37 C 1.23225(10) 0.76964(10) 0.84616(8) 0.0181(2) Uani 1 1 d .
C30 C 0.68883(10) 0.55402(9) 0.57532(9) 0.0185(2) Uani 1 1 d .
H30A H 0.6233 0.5696 0.6107 0.022 Uiso 1 1 calc R
H30B H 0.7129 0.4790 0.5694 0.022 Uiso 1 1 calc R
C1 C 0.15864(11) 0.54693(10) 0.06040(9) 0.0224(2) Uani 1 1 d .
C16 C 0.16113(11) 0.47114(10) -0.04701(9) 0.0212(2) Uani 1 1 d .
C34 C 0.49532(11) 0.65061(12) 0.17773(9) 0.0248(2) Uani 1 1 d .
C39 C 1.36325(11) 0.72250(10) 0.72933(9) 0.0210(2) Uani 1 1 d .
H39 H 1.3779 0.6957 0.6628 0.025 Uiso 1 1 calc R
C2 C 0.12730(11) 0.66741(10) 0.08478(9) 0.0219(2) Uani 1 1 d .
H2A H 0.0538 0.6648 0.0419 0.026 Uiso 1 1 calc R
H2B H 0.1856 0.7081 0.0679 0.026 Uiso 1 1 calc R
C33 C 0.54875(11) 0.75045(11) 0.25332(10) 0.0253(2) Uani 1 1 d .
H33 H 0.5570 0.8165 0.2412 0.030 Uiso 1 1 calc R
C3 C 0.11759(10) 0.73413(10) 0.19467(9) 0.0209(2) Uani 1 1 d .
H3A H 0.0739 0.8004 0.2011 0.025 Uiso 1 1 calc R
H3B H 0.0757 0.6854 0.2173 0.025 Uiso 1 1 calc R
C38 C 1.25263(10) 0.72679(10) 0.74780(9) 0.0193(2) Uani 1 1 d .
H38 H 1.1904 0.7004 0.6931 0.023 Uiso 1 1 calc R
C19 C 0.16037(10) 0.32468(10) -0.24347(9) 0.0224(2) Uani 1 1 d .
C42 C 1.32401(11) 0.80650(11) 0.92655(9) 0.0226(2) Uani 1 1 d .
H42 H 1.3104 0.8361 0.9935 0.027 Uiso 1 1 calc R
C35 C 0.48119(13) 0.55453(12) 0.19467(10) 0.0311(3) Uani 1 1 d .
H35 H 0.4440 0.4863 0.1423 0.037 Uiso 1 1 calc R
C40 C 1.45046(10) 0.75836(11) 0.81070(10) 0.0229(2) Uani 1 1 d .
C20 C 0.19511(12) 0.28774(11) -0.16927(10) 0.0265(3) Uani 1 1 d .
H20 H 0.2183 0.2134 -0.1854 0.032 Uiso 1 1 calc R
C18 C 0.12615(13) 0.43133(11) -0.22437(9) 0.0279(3) Uani 1 1 d .
H18 H 0.1028 0.4542 -0.2773 0.034 Uiso 1 1 calc R
C21 C 0.19541(12) 0.36185(11) -0.07038(10) 0.0256(3) Uani 1 1 d .
H21 H 0.2191 0.3381 -0.0180 0.031 Uiso 1 1 calc R
C36 C 0.52232(12) 0.55913(11) 0.28969(10) 0.0275(3) Uani 1 1 d .
H36 H 0.5122 0.4932 0.3017 0.033 Uiso 1 1 calc R
C17 C 0.12682(13) 0.50474(11) -0.12474(10) 0.0276(3) Uani 1 1 d .
H17 H 0.1035 0.5789 -0.1094 0.033 Uiso 1 1 calc R
C41 C 1.43461(11) 0.80012(12) 0.90927(10) 0.0259(3) Uani 1 1 d .
H41 H 1.4975 0.8236 0.9633 0.031 Uiso 1 1 calc R
O10 O 0.16861(9) 0.98087(9) 0.16805(8) 0.0303(2) Uani 1 1 d .
O9 O 0.40978(9) 0.00876(11) 0.21979(9) 0.0365(2) Uani 1 1 d .
H4 H 0.8464(14) 0.6228(14) 0.6066(12) 0.025(4) Uiso 1 1 d .
H2 H 0.3020(15) 0.8551(14) 0.4043(12) 0.026(4) Uiso 1 1 d .
H1A H 0.0093(16) 0.7876(17) 0.5245(14) 0.035(5) Uiso 1 1 d .
H3 H 0.4997(17) 0.7484(18) 0.5271(15) 0.042(5) Uiso 1 1 d .
H7 H 0.1470(19) 0.9438(19) 0.0997(17) 0.054(6) Uiso 1 1 d .
H6 H 0.408(2) 0.012(2) 0.2829(18) 0.061(7) Uiso 1 1 d .
H8 H 0.251(2) 0.992(2) 0.1779(19) 0.074(8) Uiso 1 1 d .
H5 H 0.439(2) 0.076(3) 0.227(2) 0.086(9) Uiso 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'
F F 0.0171 0.0103 '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_site_symmetry_3
C7 O1 H1A 109.5(14) .
C28 O3 H3 107.2(14) .
C9 N1 C5 110.00(9) .
C9 N1 C4 111.93(9) .
C5 N1 C4 113.21(9) .
C9 N1 H2 108.1(10) .
C5 N1 H2 106.6(10) .
C4 N1 H2 106.7(10) .
C30 N2 C26 110.16(9) .
C30 N2 C25 107.65(9) .
C26 N2 C25 112.79(9) .
C30 N2 H4 107.8(10) .
C26 N2 H4 109.2(10) .
C25 N2 H4 109.0(10) .
O3 C28 C29 105.96(9) .
O3 C28 C31 108.88(9) .
C29 C28 C31 111.62(10) .
O3 C28 C27 110.20(9) .
C29 C28 C27 106.96(9) .
C31 C28 C27 112.98(10) .
O5 C43 O6 126.72(11) .
O5 C43 C43 117.14(12) 2_566
O6 C43 C43 116.14(12) 2_566
C13 C14 C15 118.62(11) .
C13 C14 H14 120.7 .
C15 C14 H14 120.7 .
C32 C31 C36 117.43(11) .
C32 C31 C28 121.44(11) .
C36 C31 C28 120.98(11) .
C15 C10 C11 118.44(10) .
C15 C10 C7 121.47(10) .
C11 C10 C7 120.08(10) .
N2 C26 C27 112.29(9) .
N2 C26 H26A 109.1 .
C27 C26 H26A 109.1 .
N2 C26 H26B 109.1 .
C27 C26 H26B 109.1 .
H26A C26 H26B 107.9 .
O4 C22 C37 120.82(11) .
O4 C22 C23 121.22(11) .
C37 C22 C23 117.93(10) .
O8 C44 O7 126.52(11) .
O8 C44 C44 116.75(13) 2_676
O7 C44 C44 116.72(13) 2_676
O1 C7 C10 111.58(9) .
O1 C7 C6 106.29(9) .
C10 C7 C6 108.85(9) .
O1 C7 C8 110.25(9) .
C10 C7 C8 110.10(9) .
C6 C7 C8 109.69(9) .
C9 C8 C7 112.80(9) .
C9 C8 H8A 109.0 .
C7 C8 H8A 109.0 .
C9 C8 H8B 109.0 .
C7 C8 H8B 109.0 .
H8A C8 H8B 107.8 .
N1 C9 C8 111.04(9) .
N1 C9 H9A 109.4 .
C8 C9 H9A 109.4 .
N1 C9 H9B 109.4 .
C8 C9 H9B 109.4 .
H9A C9 H9B 108.0 .
C10 C15 C14 121.20(11) .
C10 C15 H15 119.4 .
C14 C15 H15 119.4 .
C26 C27 C28 112.32(10) .
C26 C27 H27A 109.1 .
C28 C27 H27A 109.1 .
C26 C27 H27B 109.1 .
C28 C27 H27B 109.1 .
H27A C27 H27B 107.9 .
N1 C5 C6 109.49(9) .
N1 C5 H5A 109.8 .
C6 C5 H5A 109.8 .
N1 C5 H5B 109.8 .
C6 C5 H5B 109.8 .
H5A C5 H5B 108.2 .
C12 C13 C14 121.71(11) .
C12 C13 Cl1 119.01(9) .
C14 C13 Cl1 119.28(10) .
C5 C6 C7 112.14(9) .
C5 C6 H6A 109.2 .
C7 C6 H6A 109.2 .
C5 C6 H6B 109.2 .
C7 C6 H6B 109.2 .
H6A C6 H6B 107.9 .
N2 C25 C24 115.58(10) .
N2 C25 H25A 108.4 .
C24 C25 H25A 108.4 .
N2 C25 H25B 108.4 .
C24 C25 H25B 108.4 .
H25A C25 H25B 107.4 .
C12 C11 C10 121.08(11) .
C12 C11 H11 119.5 .
C10 C11 H11 119.5 .
C30 C29 C28 112.23(10) .
C30 C29 H29A 109.2 .
C28 C29 H29A 109.2 .
C30 C29 H29B 109.2 .
C28 C29 H29B 109.2 .
H29A C29 H29B 107.9 .
C22 C23 C24 112.60(10) .
C22 C23 H23A 109.1 .
C24 C23 H23A 109.1 .
C22 C23 H23B 109.1 .
C24 C23 H23B 109.1 .
H23A C23 H23B 107.8 .
C33 C32 C31 121.62(12) .
C33 C32 H32 119.2 .
C31 C32 H32 119.2 .
C25 C24 C23 113.25(10) .
C25 C24 H24A 108.9 .
C23 C24 H24A 108.9 .
C25 C24 H24B 108.9 .
C23 C24 H24B 108.9 .
H24A C24 H24B 107.7 .
N1 C4 C3 113.48(10) .
N1 C4 H4A 108.9 .
C3 C4 H4A 108.9 .
N1 C4 H4B 108.9 .
C3 C4 H4B 108.9 .
H4A C4 H4B 107.7 .
C13 C12 C11 118.90(11) .
C13 C12 H12 120.6 .
C11 C12 H12 120.6 .
C38 C37 C42 119.63(11) .
C38 C37 C22 121.53(11) .
C42 C37 C22 118.85(11) .
N2 C30 C29 112.71(10) .
N2 C30 H30A 109.1 .
C29 C30 H30A 109.1 .
N2 C30 H30B 109.1 .
C29 C30 H30B 109.1 .
H30A C30 H30B 107.8 .
O2 C1 C16 120.58(11) .
O2 C1 C2 121.44(11) .
C16 C1 C2 117.96(10) .
C17 C16 C21 118.95(12) .
C17 C16 C1 122.15(11) .
C21 C16 C1 118.86(11) .
C35 C34 C33 121.08(12) .
C35 C34 Cl2 119.73(11) .
C33 C34 Cl2 119.18(11) .
C40 C39 C38 117.61(11) .
C40 C39 H39 121.2 .
C38 C39 H39 121.2 .
C1 C2 C3 113.67(10) .
C1 C2 H2A 108.8 .
C3 C2 H2A 108.8 .
C1 C2 H2B 108.8 .
C3 C2 H2B 108.8 .
H2A C2 H2B 107.7 .
C34 C33 C32 119.16(12) .
C34 C33 H33 120.4 .
C32 C33 H33 120.4 .
C4 C3 C2 111.18(10) .
C4 C3 H3A 109.4 .
C2 C3 H3A 109.4 .
C4 C3 H3B 109.4 .
C2 C3 H3B 109.4 .
H3A C3 H3B 108.0 .
C39 C38 C37 120.56(11) .
C39 C38 H38 119.7 .
C37 C38 H38 119.7 .
F1 C19 C18 118.37(12) .
F1 C19 C20 118.33(11) .
C18 C19 C20 123.27(12) .
C41 C42 C37 120.47(11) .
C41 C42 H42 119.8 .
C37 C42 H42 119.8 .
C34 C35 C36 118.96(13) .
C34 C35 H35 120.5 .
C36 C35 H35 120.5 .
F2 C40 C39 117.55(11) .
F2 C40 C41 118.51(11) .
C39 C40 C41 123.94(12) .
C19 C20 C21 118.33(12) .
C19 C20 H20 120.8 .
C21 C20 H20 120.8 .
C19 C18 C17 117.73(12) .
C19 C18 H18 121.1 .
C17 C18 H18 121.1 .
C20 C21 C16 120.62(12) .
C20 C21 H21 119.7 .
C16 C21 H21 119.7 .
C35 C36 C31 121.75(12) .
C35 C36 H36 119.1 .
C31 C36 H36 119.1 .
C18 C17 C16 121.10(12) .
C18 C17 H17 119.5 .
C16 C17 H17 119.5 .
C40 C41 C42 117.77(12) .
C40 C41 H41 121.1 .
C42 C41 H41 121.1 .
H7 O10 H8 103.6(19) .
H6 O9 H5 108(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C13 1.7396(13) .
Cl2 C34 1.7427(13) .
O1 C7 1.4227(14) .
O1 H1A 0.81(2) .
F2 C40 1.3633(14) .
O6 C43 1.2674(14) .
O5 C43 1.2437(14) .
O3 C28 1.4430(14) .
O3 H3 0.81(2) .
F1 C19 1.3514(14) .
O7 C44 1.2566(15) .
O4 C22 1.2221(15) .
N1 C9 1.5029(15) .
N1 C5 1.5038(15) .
N1 C4 1.5061(15) .
N1 H2 0.906(17) .
O2 C1 1.2179(16) .
N2 C30 1.4963(16) .
N2 C26 1.4996(14) .
N2 C25 1.5079(14) .
N2 H4 0.909(17) .
O8 C44 1.2526(15) .
C28 C29 1.5305(15) .
C28 C31 1.5336(16) .
C28 C27 1.5368(17) .
C43 C43 1.573(2) 2_566
C14 C13 1.3867(17) .
C14 C15 1.3978(17) .
C14 H14 0.9500 .
C31 C32 1.3942(16) .
C31 C36 1.3958(18) .
C10 C15 1.3943(16) .
C10 C11 1.4028(16) .
C10 C7 1.5290(16) .
C26 C27 1.5232(16) .
C26 H26A 0.9900 .
C26 H26B 0.9900 .
C22 C37 1.4918(16) .
C22 C23 1.5125(17) .
C44 C44 1.561(2) 2_676
C7 C6 1.5391(15) .
C7 C8 1.5400(16) .
C8 C9 1.5197(15) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C15 H15 0.9500 .
C27 H27A 0.9900 .
C27 H27B 0.9900 .
C5 C6 1.5182(16) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C13 C12 1.3860(16) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C25 C24 1.5156(18) .
C25 H25A 0.9900 .
C25 H25B 0.9900 .
C11 C12 1.3902(16) .
C11 H11 0.9500 .
C29 C30 1.5177(16) .
C29 H29A 0.9900 .
C29 H29B 0.9900 .
C23 C24 1.5218(16) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C32 C33 1.3908(17) .
C32 H32 0.9500 .
C24 H24A 0.9900 .
C24 H24B 0.9900 .
C4 C3 1.5226(17) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C12 H12 0.9500 .
C37 C38 1.3974(16) .
C37 C42 1.3985(17) .
C30 H30A 0.9900 .
C30 H30B 0.9900 .
C1 C16 1.4980(17) .
C1 C2 1.5187(17) .
C16 C17 1.3951(17) .
C16 C21 1.3977(17) .
C34 C35 1.380(2) .
C34 C33 1.381(2) .
C39 C40 1.3734(18) .
C39 C38 1.3909(17) .
C39 H39 0.9500 .
C2 C3 1.5271(17) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C33 H33 0.9500 .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C38 H38 0.9500 .
C19 C18 1.3747(18) .
C19 C20 1.3776(19) .
C42 C41 1.3846(18) .
C42 H42 0.9500 .
C35 C36 1.3922(18) .
C35 H35 0.9500 .
C40 C41 1.3829(18) .
C20 C21 1.3870(19) .
C20 H20 0.9500 .
C18 C17 1.3925(18) .
C18 H18 0.9500 .
C21 H21 0.9500 .
C36 H36 0.9500 .
C17 H17 0.9500 .
C41 H41 0.9500 .
O10 H7 0.92(2) .
O10 H8 0.98(3) .
O9 H6 0.92(2) .
O9 H5 0.89(3) .
