#------------------------------------------------------------------------------
#$Date: 2016-06-10 18:49:03 +0300 (Fri, 10 Jun 2016) $
#$Revision: 183312 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/90/7119024.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_7119024
loop_
_publ_author_name
'Midori Nagamoto'
'Daisuke Yamauchi'
'Takahiro Nishimura'
_publ_section_title
;
 Iridium-catalyzed asymmetric [3+2] annulation of aromatic ketimines with
 alkynes via C-H activation: unexpected inversion of the
 enantioselectivity induced by protic acids
;
_journal_name_full               Chem.Commun.
_journal_page_first              5876
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H21 Cl2 N O3, 0.1(C7 H8), 0.1(O) '
_chemical_formula_sum            'C61.4 H43.6 Cl4 N2 O6.2'
_chemical_formula_weight         1050.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           173
_symmetry_cell_setting           trigonal
_symmetry_Int_Tables_number      173
_symmetry_space_group_name_Hall  'P 6c'
_symmetry_space_group_name_H-M   'P 63'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-01-26 deposited with the CCDC.
2016-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   29.440(5)
_cell_length_b                   29.440(5)
_cell_length_c                   11.679(2)
_cell_measurement_reflns_used    4946
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      31.5
_cell_volume                     8766(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0881
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            109145
_diffrn_reflns_theta_full        64.95
_diffrn_reflns_theta_max         64.95
_diffrn_reflns_theta_min         6.95
_exptl_absorpt_coefficient_mu    2.241
_exptl_absorpt_correction_T_max  0.9566
_exptl_absorpt_correction_T_min  0.5529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             3262
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.078(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     708
_refine_ls_number_reflns         9945
_refine_ls_number_restraints     447
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0962P)²+8.5270P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1842
_refine_ls_wR_factor_ref         0.1890
_reflns_number_gt                8542
_reflns_number_total             9945
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc01398h2.cif
_cod_data_source_block           50507ya
_cod_original_formula_sum        'C61.40 H43.60 Cl4 N2 O6.20'
_cod_database_code               7119024
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, x, z+1/2'
'y, -x+y, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6458(2) 1.21496(18) 0.2756(4) 0.0414(11) Uani 1 1 d . . .
C2 C 0.6315(2) 1.19856(19) 0.3880(4) 0.0410(11) Uani 1 1 d . . .
C3 C 0.5840(2) 1.1872(2) 0.4294(4) 0.0491(12) Uani 1 1 d . . .
H1 H 0.5741 1.1761 0.5062 0.059 Uiso 1 1 calc R . .
C4 C 0.5504(2) 1.1925(2) 0.3550(4) 0.0508(13) Uani 1 1 d . . .
H2 H 0.5171 1.1855 0.3822 0.061 Uiso 1 1 calc R . .
C5 C 0.5640(2) 1.2079(2) 0.2414(5) 0.0526(13) Uani 1 1 d . . .
H3 H 0.5398 1.2104 0.1919 0.063 Uiso 1 1 calc R . .
C6 C 0.6124(2) 1.2193(2) 0.2013(4) 0.0512(13) Uani 1 1 d . . .
H4 H 0.6223 1.2299 0.1242 0.061 Uiso 1 1 calc R . .
C7 C 0.6988(2) 1.22439(19) 0.2562(4) 0.0434(11) Uani 1 1 d . . .
C8 C 0.6759(2) 1.1951(2) 0.4469(4) 0.0435(11) Uani 1 1 d . . .
C9 C 0.6568(2) 1.1371(2) 0.4748(4) 0.0415(11) Uani 1 1 d U . .
C10 C 0.6346(2) 1.0967(2) 0.3848(4) 0.0417(11) Uani 1 1 d U . .
C11 C 0.6651(3) 1.0984(2) 0.2923(4) 0.0561(14) Uani 1 1 d U . .
H5 H 0.7013 1.1242 0.2897 0.067 Uiso 1 1 calc R . .
C12 C 0.6429(4) 1.0623(3) 0.2035(5) 0.0720(19) Uani 1 1 d U . .
H6 H 0.6639 1.0625 0.1415 0.086 Uiso 1 1 calc R . .
C13 C 0.5907(3) 1.0266(3) 0.2066(5) 0.0646(17) Uani 1 1 d U . .
C14 C 0.5599(3) 1.0231(3) 0.2972(5) 0.0650(16) Uani 1 1 d U . .
H7 H 0.5241 0.9965 0.2996 0.078 Uiso 1 1 calc R . .
C15 C 0.5818(2) 1.0588(2) 0.3859(5) 0.0551(13) Uani 1 1 d U . .
H8 H 0.5604 1.0574 0.4482 0.066 Uiso 1 1 calc R . .
C16 C 0.65803(18) 1.13105(19) 0.5894(4) 0.0406(10) Uani 1 1 d U . .
C17 C 0.63796(19) 1.0805(2) 0.6492(4) 0.0436(11) Uani 1 1 d U . .
C18 C 0.6543(2) 1.04578(19) 0.6176(4) 0.0445(11) Uani 1 1 d U . .
H9 H 0.6791 1.0547 0.5575 0.053 Uiso 1 1 calc R . .
C19 C 0.6345(2) 0.9975(2) 0.6737(4) 0.0542(13) Uani 1 1 d U . .
H10 H 0.6456 0.9734 0.6529 0.065 Uiso 1 1 calc R . .
C20 C 0.5989(2) 0.98623(19) 0.7589(4) 0.0524(13) Uani 1 1 d U . .
C21 C 0.5816(2) 1.0190(2) 0.7916(4) 0.0516(13) Uani 1 1 d U . .
H11 H 0.5563 1.0092 0.8510 0.062 Uiso 1 1 calc R . .
C22 C 0.6011(2) 1.0671(2) 0.7372(4) 0.0501(12) Uani 1 1 d U . .
H12 H 0.5896 1.0907 0.7594 0.060 Uiso 1 1 calc R . .
C23 C 0.68149(19) 1.18346(19) 0.6457(4) 0.0418(11) Uani 1 1 d . . .
C24 C 0.6959(2) 1.1992(2) 0.7577(4) 0.0479(12) Uani 1 1 d . . .
C25 C 0.7205(2) 1.2524(2) 0.7852(4) 0.0462(11) Uani 1 1 d . . .
H13 H 0.7301 1.2634 0.8622 0.055 Uiso 1 1 calc R . .
C26 C 0.7308(2) 1.2886(2) 0.7015(4) 0.0491(12) Uani 1 1 d . . .
C27 C 0.71703(19) 1.2737(2) 0.5860(4) 0.0454(11) Uani 1 1 d . . .
H14 H 0.7241 1.2989 0.5277 0.054 Uiso 1 1 calc R . .
C28 C 0.69281(19) 1.2207(2) 0.5620(4) 0.0415(11) Uani 1 1 d . . .
C29 C 0.6959(3) 1.1766(2) 0.9547(4) 0.0578(14) Uani 1 1 d . . .
H31 H 0.6753 1.1930 0.9765 0.087 Uiso 1 1 calc R . .
H32 H 0.7332 1.2016 0.9659 0.087 Uiso 1 1 calc R . .
H33 H 0.6855 1.1455 1.0025 0.087 Uiso 1 1 calc R . .
C30 C 0.7669(2) 1.3590(2) 0.8345(5) 0.0613(15) Uani 1 1 d . . .
H34 H 0.7922 1.3500 0.8658 0.092 Uiso 1 1 calc R . .
H35 H 0.7345 1.3418 0.8796 0.092 Uiso 1 1 calc R . .
H36 H 0.7817 1.3971 0.8377 0.092 Uiso 1 1 calc R . .
C31 C 0.6614(2) 0.88268(19) 0.7295(4) 0.0472(12) Uani 1 1 d . . .
C32 C 0.6652(2) 0.8868(2) 0.6112(4) 0.0469(12) Uani 1 1 d . . .
C33 C 0.7071(2) 0.9307(2) 0.5614(4) 0.0552(14) Uani 1 1 d . . .
H15 H 0.7106 0.9341 0.4805 0.066 Uiso 1 1 calc R . .
C34 C 0.7435(3) 0.9689(2) 0.6325(5) 0.0631(16) Uani 1 1 d . . .
H16 H 0.7719 0.9995 0.6000 0.076 Uiso 1 1 calc R . .
C35 C 0.7393(2) 0.9637(2) 0.7514(5) 0.0618(15) Uani 1 1 d . . .
H17 H 0.7656 0.9901 0.7984 0.074 Uiso 1 1 calc R . .
C36 C 0.6972(3) 0.9202(2) 0.8016(5) 0.0612(15) Uani 1 1 d . . .
H18 H 0.6935 0.9166 0.8825 0.073 Uiso 1 1 calc R . .
C37 C 0.6134(2) 0.83188(19) 0.7560(4) 0.0455(12) Uani 1 1 d . . .
C38 C 0.6212(2) 0.83974(19) 0.5545(4) 0.0449(12) Uani 1 1 d . . .
C39 C 0.6420(2) 0.81436(19) 0.4699(4) 0.0456(12) Uani 1 1 d U . .
C40 C 0.6678(2) 0.78489(19) 0.5068(4) 0.0433(11) Uani 1 1 d U . .
C41 C 0.6983(2) 0.7966(2) 0.6067(4) 0.0559(14) Uani 1 1 d U . .
H19 H 0.7042 0.8259 0.6517 0.067 Uiso 1 1 calc R . .
C42 C 0.7198(3) 0.7669(3) 0.6411(5) 0.0632(15) Uani 1 1 d U . .
H20 H 0.7396 0.7749 0.7098 0.076 Uiso 1 1 calc R . .
C43 C 0.7122(2) 0.7251(2) 0.5741(4) 0.0529(13) Uani 1 1 d U . .
C44 C 0.6832(2) 0.7126(2) 0.4758(4) 0.0449(11) Uani 1 1 d U . .
H21 H 0.6785 0.6837 0.4307 0.054 Uiso 1 1 calc R . .
C45 C 0.6609(2) 0.74168(19) 0.4422(4) 0.0424(11) Uani 1 1 d U . .
H22 H 0.6405 0.7325 0.3742 0.051 Uiso 1 1 calc R . .
C46 C 0.6319(2) 0.82325(18) 0.3623(4) 0.0428(11) Uani 1 1 d U . .
C47 C 0.6590(2) 0.81944(19) 0.2571(4) 0.0442(11) Uani 1 1 d U . .
C48 C 0.7127(2) 0.8476(2) 0.2521(4) 0.0465(11) Uani 1 1 d U . .
H23 H 0.7321 0.8663 0.3177 0.056 Uiso 1 1 calc R . .
C49 C 0.7388(2) 0.8492(2) 0.1523(5) 0.0556(13) Uani 1 1 d U . .
H24 H 0.7760 0.8690 0.1488 0.067 Uiso 1 1 calc R . .
C50 C 0.7105(3) 0.8220(2) 0.0600(4) 0.0585(15) Uani 1 1 d U . .
C51 C 0.6582(3) 0.7928(2) 0.0611(4) 0.0565(14) Uani 1 1 d U . .
H25 H 0.6396 0.7735 -0.0047 0.068 Uiso 1 1 calc R . .
C52 C 0.6319(2) 0.7913(2) 0.1604(4) 0.0496(12) Uani 1 1 d U . .
H26 H 0.5948 0.7707 0.1627 0.059 Uiso 1 1 calc R . .
C53 C 0.5974(2) 0.84574(19) 0.3645(4) 0.0424(11) Uani 1 1 d . . .
C54 C 0.5720(2) 0.85772(19) 0.2779(4) 0.0439(11) Uani 1 1 d . . .
C55 C 0.5402(2) 0.8772(2) 0.3081(4) 0.0456(12) Uani 1 1 d . . .
H27 H 0.5230 0.8856 0.2500 0.055 Uiso 1 1 calc R . .
C56 C 0.5325(2) 0.8851(2) 0.4224(4) 0.0467(12) Uani 1 1 d . . .
C57 C 0.5562(2) 0.87356(19) 0.5098(4) 0.0470(12) Uani 1 1 d . . .
H28 H 0.5507 0.8787 0.5878 0.056 Uiso 1 1 calc R . .
C58 C 0.5886(2) 0.85381(19) 0.4783(4) 0.0435(11) Uani 1 1 d . . .
C59 C 0.5521(2) 0.8551(2) 0.0795(4) 0.0508(13) Uani 1 1 d . . .
H37 H 0.5580 0.8910 0.0809 0.076 Uiso 1 1 calc R . .
H38 H 0.5146 0.8301 0.0895 0.076 Uiso 1 1 calc R . .
H39 H 0.5638 0.8487 0.0059 0.076 Uiso 1 1 calc R . .
C60 C 0.4925(3) 0.9187(3) 0.5506(5) 0.0634(16) Uani 1 1 d . . .
H40 H 0.5265 0.9476 0.5759 0.095 Uiso 1 1 calc R . .
H41 H 0.4811 0.8889 0.6030 0.095 Uiso 1 1 calc R . .
H42 H 0.4665 0.9302 0.5504 0.095 Uiso 1 1 calc R . .
N1 N 0.71651(16) 1.21649(16) 0.3580(3) 0.0434(9) Uani 1 1 d . . .
H29 H 0.7490 1.2235 0.3693 0.052 Uiso 1 1 calc R . .
N2 N 0.59241(18) 0.80777(16) 0.6551(3) 0.0465(10) Uani 1 1 d . . .
H30 H 0.5645 0.7763 0.6500 0.056 Uiso 1 1 calc R . .
O1 O 0.72426(13) 1.23637(13) 0.1661(3) 0.0463(8) Uani 1 1 d . . .
O2 O 0.68630(16) 1.16115(14) 0.8360(3) 0.0553(9) Uani 1 1 d . . .
O3 O 0.75572(16) 1.34212(15) 0.7200(3) 0.0591(10) Uani 1 1 d . . .
O4 O 0.59496(14) 0.81404(13) 0.8513(2) 0.0482(8) Uani 1 1 d . . .
O5 O 0.58060(14) 0.84870(14) 0.1692(3) 0.0466(8) Uani 1 1 d . . .
O6 O 0.49758(16) 0.90305(15) 0.4373(3) 0.0565(9) Uani 1 1 d . . .
Cl1 Cl 0.57326(7) 0.92494(5) 0.82728(11) 0.0717(5) Uani 1 1 d U . .
Cl2 Cl 0.56286(11) 0.98442(7) 0.09089(13) 0.1024(8) Uani 1 1 d U . .
Cl3 Cl 0.73872(7) 0.68671(6) 0.61970(11) 0.0647(4) Uani 1 1 d U . .
Cl4 Cl 0.74434(9) 0.82645(9) -0.06874(12) 0.0858(6) Uani 1 1 d U . .
C61 C 0.1673(11) 0.0805(11) 0.957(2) 0.103(7) Uani 0.20 1 d PGDU . .
H43 H 0.1825 0.0629 0.9960 0.123 Uiso 0.20 1 calc PR . .
C62 C 0.1676(11) 0.1234(11) 1.008(2) 0.109(7) Uani 0.20 1 d PGU . .
H44 H 0.1831 0.1351 1.0815 0.131 Uiso 0.20 1 calc PR . .
C64 C 0.1454(12) 0.1491(10) 0.952(3) 0.107(7) Uani 0.20 1 d PGU . .
H45 H 0.1456 0.1784 0.9863 0.128 Uiso 0.20 1 calc PR . .
C65 C 0.1229(12) 0.1319(11) 0.844(3) 0.112(7) Uani 0.20 1 d PGU . .
H46 H 0.1077 0.1495 0.8056 0.135 Uiso 0.20 1 calc PR . .
C66 C 0.1225(11) 0.0890(11) 0.793(2) 0.108(7) Uani 0.20 1 d PGDU . .
H47 H 0.1071 0.0773 0.7201 0.130 Uiso 0.20 1 calc PR . .
C67 C 0.1448(12) 0.0633(10) 0.850(2) 0.102(7) Uani 0.20 1 d PGDU . .
C68 C 0.1464(17) 0.0183(14) 0.792(3) 0.100(9) Uani 0.20 1 d PDU . .
H48 H 0.1648 0.0056 0.8407 0.150 Uiso 0.20 1 calc PR . .
H49 H 0.1650 0.0303 0.7184 0.150 Uiso 0.20 1 calc PR . .
H50 H 0.1105 -0.0103 0.7777 0.150 Uiso 0.20 1 calc PR . .
O7 O 0.3333 0.6667 1.003(8) 0.27(4) Uiso 0.30 3 d SP . .
O8 O 0.0000 0.0000 0.632(16) 0.46(8) Uiso 0.30 3 d SP . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_1
_geom_angle_site_symmetry_3
C6 C1 C2 121.8(5) . .
C6 C1 C7 129.5(5) . .
C2 C1 C7 108.7(4) . .
C3 C2 C1 121.1(5) . .
C3 C2 C8 129.6(4) . .
C1 C2 C8 109.3(4) . .
C2 C3 C4 117.2(5) . .
C2 C3 H1 121.4 . .
C4 C3 H1 121.4 . .
C3 C4 C5 122.0(5) . .
C3 C4 H2 119.0 . .
C5 C4 H2 119.0 . .
C6 C5 C4 119.9(5) . .
C6 C5 H3 120.1 . .
C4 C5 H3 120.1 . .
C1 C6 C5 118.0(5) . .
C1 C6 H4 121.0 . .
C5 C6 H4 121.0 . .
O1 C7 N1 124.3(5) . .
O1 C7 C1 128.6(5) . .
N1 C7 C1 107.1(4) . .
N1 C8 C28 115.1(4) . .
N1 C8 C2 101.2(4) . .
C28 C8 C2 116.8(4) . .
N1 C8 C9 113.2(4) . .
C28 C8 C9 102.4(4) . .
C2 C8 C9 108.5(4) . .
C16 C9 C10 129.1(5) . .
C16 C9 C8 109.6(4) . .
C10 C9 C8 120.9(4) . .
C15 C10 C11 118.7(5) . .
C15 C10 C9 120.6(4) . .
C11 C10 C9 120.6(5) . .
C10 C11 C12 120.2(6) . .
C10 C11 H5 119.9 . .
C12 C11 H5 119.9 . .
C13 C12 C11 119.2(6) . .
C13 C12 H6 120.4 . .
C11 C12 H6 120.4 . .
C12 C13 C14 122.0(5) . .
C12 C13 Cl2 118.5(5) . .
C14 C13 Cl2 119.5(6) . .
C13 C14 C15 119.0(6) . .
C13 C14 H7 120.5 . .
C15 C14 H7 120.5 . .
C14 C15 C10 120.8(5) . .
C14 C15 H8 119.6 . .
C10 C15 H8 119.6 . .
C9 C16 C17 125.3(5) . .
C9 C16 C23 109.2(4) . .
C17 C16 C23 125.5(4) . .
C18 C17 C22 119.7(5) . .
C18 C17 C16 120.6(4) . .
C22 C17 C16 119.6(5) . .
C17 C18 C19 120.3(5) . .
C17 C18 H9 119.9 . .
C19 C18 H9 119.9 . .
C20 C19 C18 118.0(5) . .
C20 C19 H10 121.0 . .
C18 C19 H10 121.0 . .
C21 C20 C19 123.5(5) . .
C21 C20 Cl1 118.7(4) . .
C19 C20 Cl1 117.7(5) . .
C20 C21 C22 119.1(5) . .
C20 C21 H11 120.5 . .
C22 C21 H11 120.5 . .
C21 C22 C17 119.4(5) . .
C21 C22 H12 120.3 . .
C17 C22 H12 120.3 . .
C28 C23 C24 119.5(5) . .
C28 C23 C16 108.2(4) . .
C24 C23 C16 132.0(4) . .
O2 C24 C23 117.3(4) . .
O2 C24 C25 123.1(4) . .
C23 C24 C25 119.6(5) . .
C26 C25 C24 120.0(5) . .
C26 C25 H13 120.0 . .
C24 C25 H13 120.0 . .
C25 C26 O3 124.2(5) . .
C25 C26 C27 121.6(5) . .
O3 C26 C27 114.2(5) . .
C28 C27 C26 116.8(5) . .
C28 C27 H14 121.6 . .
C26 C27 H14 121.6 . .
C27 C28 C23 122.5(4) . .
C27 C28 C8 127.2(4) . .
C23 C28 C8 110.3(4) . .
O2 C29 H31 109.5 . .
O2 C29 H32 109.5 . .
H31 C29 H32 109.5 . .
O2 C29 H33 109.5 . .
H31 C29 H33 109.5 . .
H32 C29 H33 109.5 . .
O3 C30 H34 109.5 . .
O3 C30 H35 109.5 . .
H34 C30 H35 109.5 . .
O3 C30 H36 109.5 . .
H34 C30 H36 109.5 . .
H35 C30 H36 109.5 . .
C36 C31 C32 123.1(5) . .
C36 C31 C37 130.0(5) . .
C32 C31 C37 106.9(4) . .
C31 C32 C33 119.6(5) . .
C31 C32 C38 111.3(4) . .
C33 C32 C38 129.1(4) . .
C34 C33 C32 118.2(5) . .
C34 C33 H15 120.9 . .
C32 C33 H15 120.9 . .
C33 C34 C35 121.4(5) . .
C33 C34 H16 119.3 . .
C35 C34 H16 119.3 . .
C36 C35 C34 120.7(5) . .
C36 C35 H17 119.7 . .
C34 C35 H17 119.7 . .
C31 C36 C35 117.1(5) . .
C31 C36 H18 121.5 . .
C35 C36 H18 121.5 . .
O4 C37 N2 124.9(5) . .
O4 C37 C31 127.6(4) . .
N2 C37 C31 107.5(4) . .
N2 C38 C32 101.2(3) . .
N2 C38 C58 113.8(4) . .
C32 C38 C58 112.4(4) . .
N2 C38 C39 116.2(4) . .
C32 C38 C39 111.3(4) . .
C58 C38 C39 102.5(4) . .
C46 C39 C40 128.0(5) . .
C46 C39 C38 109.0(4) . .
C40 C39 C38 123.0(4) . .
C45 C40 C41 116.9(5) . .
C45 C40 C39 119.5(4) . .
C41 C40 C39 123.5(5) . .
C42 C41 C40 121.9(5) . .
C42 C41 H19 119.1 . .
C40 C41 H19 119.1 . .
C41 C42 C43 118.8(5) . .
C41 C42 H20 120.6 . .
C43 C42 H20 120.6 . .
C44 C43 C42 121.3(5) . .
C44 C43 Cl3 120.1(4) . .
C42 C43 Cl3 118.6(4) . .
C43 C44 C45 120.1(5) . .
C43 C44 H21 120.0 . .
C45 C44 H21 120.0 . .
C44 C45 C40 121.0(5) . .
C44 C45 H22 119.5 . .
C40 C45 H22 119.5 . .
C39 C46 C53 110.0(4) . .
C39 C46 C47 124.9(5) . .
C53 C46 C47 124.4(4) . .
C48 C47 C52 118.0(5) . .
C48 C47 C46 119.1(4) . .
C52 C47 C46 122.7(5) . .
C47 C48 C49 120.6(5) . .
C47 C48 H23 119.7 . .
C49 C48 H23 119.7 . .
C50 C49 C48 119.0(6) . .
C50 C49 H24 120.5 . .
C48 C49 H24 120.5 . .
C51 C50 C49 122.9(5) . .
C51 C50 Cl4 118.7(5) . .
C49 C50 Cl4 118.4(5) . .
C50 C51 C52 118.4(5) . .
C50 C51 H25 120.8 . .
C52 C51 H25 120.8 . .
C51 C52 C47 121.1(5) . .
C51 C52 H26 119.5 . .
C47 C52 H26 119.5 . .
C58 C53 C54 118.5(5) . .
C58 C53 C46 108.8(4) . .
C54 C53 C46 132.7(4) . .
O5 C54 C55 124.2(5) . .
O5 C54 C53 117.0(4) . .
C55 C54 C53 118.8(4) . .
C54 C55 C56 121.5(5) . .
C54 C55 H27 119.3 . .
C56 C55 H27 119.3 . .
C57 C56 O6 124.6(4) . .
C57 C56 C55 121.7(5) . .
O6 C56 C55 113.6(4) . .
C56 C57 C58 116.5(4) . .
C56 C57 H28 121.7 . .
C58 C57 H28 121.7 . .
C57 C58 C53 123.1(5) . .
C57 C58 C38 128.3(4) . .
C53 C58 C38 108.6(4) . .
O5 C59 H37 109.5 . .
O5 C59 H38 109.5 . .
H37 C59 H38 109.5 . .
O5 C59 H39 109.5 . .
H37 C59 H39 109.5 . .
H38 C59 H39 109.5 . .
O6 C60 H40 109.5 . .
O6 C60 H41 109.5 . .
H40 C60 H41 109.5 . .
O6 C60 H42 109.5 . .
H40 C60 H42 109.5 . .
H41 C60 H42 109.5 . .
C7 N1 C8 113.1(4) . .
C7 N1 H29 123.4 . .
C8 N1 H29 123.4 . .
C37 N2 C38 113.1(4) . .
C37 N2 H30 123.5 . .
C38 N2 H30 123.5 . .
C24 O2 C29 117.4(4) . .
C26 O3 C30 116.7(4) . .
C54 O5 C59 119.3(4) . .
C56 O6 C60 117.1(4) . .
C62 C61 C67 120.0 . .
C62 C61 H43 120.0 . .
C67 C61 H43 120.0 . .
C64 C62 C61 120.0 . .
C64 C62 H44 120.0 . .
C61 C62 H44 120.0 . .
C65 C64 C62 120.0 . .
C65 C64 H45 120.0 . .
C62 C64 H45 120.0 . .
C66 C65 C64 120.0 . .
C66 C65 H46 120.0 . .
C64 C65 H46 120.0 . .
C65 C66 C67 120.0 . .
C65 C66 H47 120.0 . .
C67 C66 H47 120.0 . .
C66 C67 C61 120.0 . .
C66 C67 C68 119.5(11) . .
C61 C67 C68 120.4(11) . .
C67 C68 H48 109.5 . .
C67 C68 H49 109.5 . .
H48 C68 H49 109.5 . .
C67 C68 H50 109.5 . .
H48 C68 H50 109.5 . .
H49 C68 H50 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.364(7) .
C1 C2 1.389(7) .
C1 C7 1.461(7) .
C2 C3 1.356(7) .
C2 C8 1.525(7) .
C3 C4 1.380(8) .
C3 H1 0.9500 .
C4 C5 1.394(8) .
C4 H2 0.9500 .
C5 C6 1.372(8) .
C5 H3 0.9500 .
C6 H4 0.9500 .
C7 O1 1.236(6) .
C7 N1 1.364(6) .
C8 N1 1.466(6) .
C8 C28 1.499(7) .
C8 C9 1.542(7) .
C9 C16 1.354(6) .
C9 C10 1.472(7) .
C10 C15 1.388(8) .
C10 C11 1.391(7) .
C11 C12 1.391(9) .
C11 H5 0.9500 .
C12 C13 1.361(10) .
C12 H6 0.9500 .
C13 C14 1.362(9) .
C13 Cl2 1.739(6) .
C14 C15 1.384(8) .
C14 H7 0.9500 .
C15 H8 0.9500 .
C16 C17 1.474(7) .
C16 C23 1.491(7) .
C17 C18 1.380(7) .
C17 C22 1.400(7) .
C18 C19 1.400(8) .
C18 H9 0.9500 .
C19 C20 1.360(8) .
C19 H10 0.9500 .
C20 C21 1.354(8) .
C20 Cl1 1.761(5) .
C21 C22 1.387(8) .
C21 H11 0.9500 .
C22 H12 0.9500 .
C23 C28 1.381(7) .
C23 C24 1.382(7) .
C24 O2 1.361(6) .
C24 C25 1.395(8) .
C25 C26 1.365(7) .
C25 H13 0.9500 .
C26 O3 1.383(7) .
C26 C27 1.413(7) .
C27 C28 1.380(7) .
C27 H14 0.9500 .
C29 O2 1.443(6) .
C29 H31 0.9800 .
C29 H32 0.9800 .
C29 H33 0.9800 .
C30 O3 1.407(7) .
C30 H34 0.9800 .
C30 H35 0.9800 .
C30 H36 0.9800 .
C31 C36 1.370(8) .
C31 C32 1.387(6) .
C31 C37 1.489(7) .
C32 C33 1.390(7) .
C32 C38 1.498(7) .
C33 C34 1.378(8) .
C33 H15 0.9500 .
C34 C35 1.395(8) .
C34 H16 0.9500 .
C35 C36 1.390(9) .
C35 H17 0.9500 .
C36 H18 0.9500 .
C37 O4 1.234(6) .
C37 N2 1.355(6) .
C38 N2 1.478(6) .
C38 C58 1.510(7) .
C38 C39 1.539(7) .
C39 C46 1.347(7) .
C39 C40 1.476(7) .
C40 C45 1.404(7) .
C40 C41 1.405(7) .
C41 C42 1.373(8) .
C41 H19 0.9500 .
C42 C43 1.377(8) .
C42 H20 0.9500 .
C43 C44 1.366(7) .
C43 Cl3 1.748(6) .
C44 C45 1.371(7) .
C44 H21 0.9500 .
C45 H22 0.9500 .
C46 C53 1.465(8) .
C46 C47 1.500(7) .
C47 C48 1.369(8) .
C47 C52 1.392(7) .
C48 C49 1.385(7) .
C48 H23 0.9500 .
C49 C50 1.353(9) .
C49 H24 0.9500 .
C50 C51 1.336(9) .
C50 Cl4 1.771(5) .
C51 C52 1.383(7) .
C51 H25 0.9500 .
C52 H26 0.9500 .
C53 C58 1.397(6) .
C53 C54 1.403(7) .
C54 O5 1.347(6) .
C54 C55 1.366(7) .
C55 C56 1.393(7) .
C55 H27 0.9500 .
C56 C57 1.373(7) .
C56 O6 1.380(6) .
C57 C58 1.394(7) .
C57 H28 0.9500 .
C59 O5 1.413(6) .
C59 H37 0.9800 .
C59 H38 0.9800 .
C59 H39 0.9800 .
C60 O6 1.432(6) .
C60 H40 0.9800 .
C60 H41 0.9800 .
C60 H42 0.9800 .
N1 H29 0.8800 .
N2 H30 0.8800 .
C61 C62 1.3900 .
C61 C67 1.3900 .
C61 H43 0.9500 .
C62 C64 1.3900 .
C62 H44 0.9500 .
C64 C65 1.3900 .
C64 H45 0.9500 .
C65 C66 1.3900 .
C65 H46 0.9500 .
C66 C67 1.3900 .
C66 H47 0.9500 .
C67 C68 1.51(3) .
C68 H48 0.9800 .
C68 H49 0.9800 .
C68 H50 0.9800 .
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
N1 H29 O4 0.88 2.00 2.835(5) 159.0 6_564
N2 H30 O1 0.88 2.00 2.822(6) 154.0 5_655
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
C6 C1 C2 C3 -1.5(7) . . . .
C7 C1 C2 C3 179.7(4) . . . .
C6 C1 C2 C8 177.1(4) . . . .
C7 C1 C2 C8 -1.7(5) . . . .
C1 C2 C3 C4 0.2(7) . . . .
C8 C2 C3 C4 -178.1(5) . . . .
C2 C3 C4 C5 1.2(8) . . . .
C3 C4 C5 C6 -1.4(8) . . . .
C2 C1 C6 C5 1.2(7) . . . .
C7 C1 C6 C5 179.8(5) . . . .
C4 C5 C6 C1 0.2(7) . . . .
C6 C1 C7 O1 -3.3(9) . . . .
C2 C1 C7 O1 175.4(5) . . . .
C6 C1 C7 N1 177.9(5) . . . .
C2 C1 C7 N1 -3.4(5) . . . .
C3 C2 C8 N1 -175.9(5) . . . .
C1 C2 C8 N1 5.6(5) . . . .
C3 C2 C8 C28 -50.2(7) . . . .
C1 C2 C8 C28 131.4(4) . . . .
C3 C2 C8 C9 64.8(6) . . . .
C1 C2 C8 C9 -113.7(4) . . . .
N1 C8 C9 C16 129.8(4) . . . .
C28 C8 C9 C16 5.3(5) . . . .
C2 C8 C9 C16 -118.7(4) . . . .
N1 C8 C9 C10 -57.6(6) . . . .
C28 C8 C9 C10 177.9(4) . . . .
C2 C8 C9 C10 53.9(6) . . . .
C16 C9 C10 C15 59.3(8) . . . .
C8 C9 C10 C15 -111.7(6) . . . .
C16 C9 C10 C11 -126.0(6) . . . .
C8 C9 C10 C11 63.0(6) . . . .
C15 C10 C11 C12 -0.6(8) . . . .
C9 C10 C11 C12 -175.4(5) . . . .
C10 C11 C12 C13 2.2(8) . . . .
C11 C12 C13 C14 -3.9(9) . . . .
C11 C12 C13 Cl2 176.3(4) . . . .
C12 C13 C14 C15 3.9(9) . . . .
Cl2 C13 C14 C15 -176.3(5) . . . .
C13 C14 C15 C10 -2.2(9) . . . .
C11 C10 C15 C14 0.5(8) . . . .
C9 C10 C15 C14 175.3(5) . . . .
C10 C9 C16 C17 2.1(9) . . . .
C8 C9 C16 C17 173.9(4) . . . .
C10 C9 C16 C23 -176.2(5) . . . .
C8 C9 C16 C23 -4.4(6) . . . .
C9 C16 C17 C18 53.5(7) . . . .
C23 C16 C17 C18 -128.4(5) . . . .
C9 C16 C17 C22 -125.2(5) . . . .
C23 C16 C17 C22 52.9(7) . . . .
C22 C17 C18 C19 -0.5(7) . . . .
C16 C17 C18 C19 -179.1(4) . . . .
C17 C18 C19 C20 0.3(7) . . . .
C18 C19 C20 C21 0.4(8) . . . .
C18 C19 C20 Cl1 178.8(4) . . . .
C19 C20 C21 C22 -0.8(8) . . . .
Cl1 C20 C21 C22 -179.2(4) . . . .
C20 C21 C22 C17 0.6(8) . . . .
C18 C17 C22 C21 0.0(7) . . . .
C16 C17 C22 C21 178.7(5) . . . .
C9 C16 C23 C28 1.7(6) . . . .
C17 C16 C23 C28 -176.7(5) . . . .
C9 C16 C23 C24 -173.0(5) . . . .
C17 C16 C23 C24 8.6(9) . . . .
C28 C23 C24 O2 -176.7(5) . . . .
C16 C23 C24 O2 -2.5(9) . . . .
C28 C23 C24 C25 1.6(8) . . . .
C16 C23 C24 C25 175.8(5) . . . .
O2 C24 C25 C26 177.4(5) . . . .
C23 C24 C25 C26 -0.8(8) . . . .
C24 C25 C26 O3 -178.9(5) . . . .
C24 C25 C26 C27 0.1(8) . . . .
C25 C26 C27 C28 -0.1(8) . . . .
O3 C26 C27 C28 178.9(4) . . . .
C26 C27 C28 C23 1.0(7) . . . .
C26 C27 C28 C8 -178.0(5) . . . .
C24 C23 C28 C27 -1.8(8) . . . .
C16 C23 C28 C27 -177.2(4) . . . .
C24 C23 C28 C8 177.4(5) . . . .
C16 C23 C28 C8 1.9(6) . . . .
N1 C8 C28 C27 51.6(7) . . . .
C2 C8 C28 C27 -66.8(7) . . . .
C9 C8 C28 C27 174.8(5) . . . .
N1 C8 C28 C23 -127.5(4) . . . .
C2 C8 C28 C23 114.1(5) . . . .
C9 C8 C28 C23 -4.3(5) . . . .
C36 C31 C32 C33 0.2(9) . . . .
C37 C31 C32 C33 -179.4(5) . . . .
C36 C31 C32 C38 179.1(5) . . . .
C37 C31 C32 C38 -0.5(6) . . . .
C31 C32 C33 C34 -0.4(9) . . . .
C38 C32 C33 C34 -179.1(6) . . . .
C32 C33 C34 C35 1.4(10) . . . .
C33 C34 C35 C36 -2.0(10) . . . .
C32 C31 C36 C35 -0.8(9) . . . .
C37 C31 C36 C35 178.7(6) . . . .
C34 C35 C36 C31 1.7(9) . . . .
C36 C31 C37 O4 3.0(10) . . . .
C32 C31 C37 O4 -177.4(5) . . . .
C36 C31 C37 N2 -177.4(6) . . . .
C32 C31 C37 N2 2.2(6) . . . .
C31 C32 C38 N2 -1.1(6) . . . .
C33 C32 C38 N2 177.6(6) . . . .
C31 C32 C38 C58 120.6(5) . . . .
C33 C32 C38 C58 -60.7(7) . . . .
C31 C32 C38 C39 -125.2(5) . . . .
C33 C32 C38 C39 53.5(7) . . . .
N2 C38 C39 C46 135.9(5) . . . .
C32 C38 C39 C46 -109.0(5) . . . .
C58 C38 C39 C46 11.3(5) . . . .
N2 C38 C39 C40 -43.3(7) . . . .
C32 C38 C39 C40 71.7(6) . . . .
C58 C38 C39 C40 -167.9(5) . . . .
C46 C39 C40 C45 -33.1(8) . . . .
C38 C39 C40 C45 146.0(5) . . . .
C46 C39 C40 C41 148.9(6) . . . .
C38 C39 C40 C41 -32.0(8) . . . .
C45 C40 C41 C42 -1.0(8) . . . .
C39 C40 C41 C42 177.0(6) . . . .
C40 C41 C42 C43 1.5(9) . . . .
C41 C42 C43 C44 -0.9(9) . . . .
C41 C42 C43 Cl3 -178.9(5) . . . .
C42 C43 C44 C45 -0.2(8) . . . .
Cl3 C43 C44 C45 177.8(4) . . . .
C43 C44 C45 C40 0.7(8) . . . .
C41 C40 C45 C44 -0.1(7) . . . .
C39 C40 C45 C44 -178.2(5) . . . .
C40 C39 C46 C53 169.7(5) . . . .
C38 C39 C46 C53 -9.5(6) . . . .
C40 C39 C46 C47 -20.0(9) . . . .
C38 C39 C46 C47 160.8(5) . . . .
C39 C46 C47 C48 -54.2(7) . . . .
C53 C46 C47 C48 114.8(6) . . . .
C39 C46 C47 C52 130.6(6) . . . .
C53 C46 C47 C52 -60.5(7) . . . .
C52 C47 C48 C49 1.9(7) . . . .
C46 C47 C48 C49 -173.6(5) . . . .
C47 C48 C49 C50 -0.6(8) . . . .
C48 C49 C50 C51 -1.1(9) . . . .
C48 C49 C50 Cl4 177.5(4) . . . .
C49 C50 C51 C52 1.3(9) . . . .
Cl4 C50 C51 C52 -177.2(4) . . . .
C50 C51 C52 C47 0.1(8) . . . .
C48 C47 C52 C51 -1.7(7) . . . .
C46 C47 C52 C51 173.7(5) . . . .
C39 C46 C53 C58 3.7(6) . . . .
C47 C46 C53 C58 -166.7(5) . . . .
C39 C46 C53 C54 -173.7(5) . . . .
C47 C46 C53 C54 15.9(9) . . . .
C58 C53 C54 O5 -179.0(4) . . . .
C46 C53 C54 O5 -1.8(8) . . . .
C58 C53 C54 C55 0.6(7) . . . .
C46 C53 C54 C55 177.7(5) . . . .
O5 C54 C55 C56 179.3(5) . . . .
C53 C54 C55 C56 -0.2(8) . . . .
C54 C55 C56 C57 -0.3(8) . . . .
C54 C55 C56 O6 -177.5(5) . . . .
O6 C56 C57 C58 177.3(5) . . . .
C55 C56 C57 C58 0.4(8) . . . .
C56 C57 C58 C53 0.0(8) . . . .
C56 C57 C58 C38 177.4(5) . . . .
C54 C53 C58 C57 -0.5(8) . . . .
C46 C53 C58 C57 -178.3(5) . . . .
C54 C53 C58 C38 -178.3(4) . . . .
C46 C53 C58 C38 3.9(6) . . . .
N2 C38 C58 C57 47.1(7) . . . .
C32 C38 C58 C57 -67.1(7) . . . .
C39 C38 C58 C57 173.4(5) . . . .
N2 C38 C58 C53 -135.2(4) . . . .
C32 C38 C58 C53 110.6(5) . . . .
C39 C38 C58 C53 -8.9(5) . . . .
O1 C7 N1 C8 -171.4(4) . . . .
C1 C7 N1 C8 7.5(5) . . . .
C28 C8 N1 C7 -134.9(4) . . . .
C2 C8 N1 C7 -8.1(5) . . . .
C9 C8 N1 C7 107.8(5) . . . .
O4 C37 N2 C38 176.6(5) . . . .
C31 C37 N2 C38 -3.1(6) . . . .
C32 C38 N2 C37 2.6(6) . . . .
C58 C38 N2 C37 -118.1(5) . . . .
C39 C38 N2 C37 123.2(5) . . . .
C23 C24 O2 C29 -173.2(5) . . . .
C25 C24 O2 C29 8.5(8) . . . .
C25 C26 O3 C30 -5.5(8) . . . .
C27 C26 O3 C30 175.4(5) . . . .
C55 C54 O5 C59 -5.8(7) . . . .
C53 C54 O5 C59 173.8(4) . . . .
C57 C56 O6 C60 10.7(8) . . . .
C55 C56 O6 C60 -172.1(5) . . . .
C67 C61 C62 C64 0.0 . . . .
C61 C62 C64 C65 0.0 . . . .
C62 C64 C65 C66 0.0 . . . .
C64 C65 C66 C67 0.0 . . . .
C65 C66 C67 C61 0.0 . . . .
C65 C66 C67 C68 -177(3) . . . .
C62 C61 C67 C66 0.0 . . . .
C62 C61 C67 C68 177(3) . . . .
