#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/81/4108186.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_4108186
loop_
_publ_author_name
'Koji Fukamizu'
'Yoshihiro Miyake'
'Yoshiaki Nishibayashi'
_publ_section_title
;
 Ruthenium-Catalyzed Enantioselective Carbon-Carbon Bond Forming Reaction
 via Allenylidene-Ene Process: Synthetic Approach to Chiral Heterocycles
 Such As Chromane, Thiochromane, and 1,2,3,4-Tetrahydroquinoline
 Derivatives
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10498
_journal_page_last               10499
_journal_paper_doi               10.1021/ja8038745
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C23 H17 Cl O '
_chemical_formula_sum            'C23 H17 Cl O'
_chemical_formula_weight         344.84
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            12
_cell_length_a                   9.9845(9)
_cell_length_b                   20.7418(15)
_cell_length_c                   25.4506(19)
_cell_measurement_reflns_used    22530
_cell_measurement_temperature    173.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     5270.7(7)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SHELXS97
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.306
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            82121
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       needle
_exptl_crystal_F_000             2160.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.46
_refine_diff_density_min         -1.50
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  5368 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.03(9)
_refine_ls_extinction_coef       201(104)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     729
_refine_ls_number_reflns         12013
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0011Fo² + 0.1465σ(Fo²)]/(4Fo²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2058
_reflns_number_gt                2623
_reflns_number_total             12013
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja8038745-file004_3.cif
_cod_data_source_block           '_3k'
_cod_original_formula_sum        'C23 H17 Cl O '
_cod_database_code               4108186
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+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
Cl(1) Cl 0.9446(2) 0.60915(9) 0.16828(6) 0.0875(7) Uani 1.00 1 d .
Cl(2) Cl 0.6478(2) 0.67342(8) 0.59311(7) 0.0780(6) Uani 1.00 1 d .
Cl(3) Cl 0.3307(2) 0.19481(8) 0.40818(7) 0.0726(5) Uani 1.00 1 d .
O(1) O 0.9885(4) 0.6835(2) 0.51843(15) 0.0653(15) Uani 1.00 1 d .
O(2) O 0.6710(5) 0.2747(2) 0.4465(2) 0.0773(17) Uani 1.00 1 d .
O(3) O 0.3042(4) 0.53532(18) 0.18121(15) 0.0557(13) Uani 1.00 1 d .
C(1) C 0.9988(6) 0.6169(3) 0.5174(2) 0.056(2) Uani 1.00 1 d .
C(2) C 1.0588(7) 0.5900(3) 0.5631(2) 0.065(2) Uani 1.00 1 d .
C(3) C 1.0725(7) 0.5249(3) 0.5665(2) 0.067(2) Uani 1.00 1 d .
C(4) C 1.0304(6) 0.4840(3) 0.5263(2) 0.058(2) Uani 1.00 1 d .
C(5) C 1.0454(7) 0.4159(3) 0.5297(3) 0.072(2) Uani 1.00 1 d .
C(6) C 1.0041(7) 0.3775(3) 0.4903(3) 0.072(2) Uani 1.00 1 d .
C(7) C 0.9502(7) 0.4029(3) 0.4437(2) 0.062(2) Uani 1.00 1 d .
C(8) C 0.9331(6) 0.4688(2) 0.4396(2) 0.054(2) Uani 1.00 1 d .
C(9) C 0.9728(6) 0.5107(2) 0.4803(2) 0.0492(19) Uani 1.00 1 d .
C(10) C 0.9580(6) 0.5793(2) 0.4768(2) 0.0483(19) Uani 1.00 1 d .
C(11) C 0.8941(6) 0.6093(2) 0.4289(2) 0.0453(18) Uani 1.00 1 d .
C(12) C 0.7507(8) 0.5962(3) 0.4272(2) 0.055(2) Uani 1.00 1 d .
C(13) C 0.6329(9) 0.5865(2) 0.4268(2) 0.065(2) Uani 1.00 1 d .
C(14) C 0.8974(7) 0.7102(2) 0.4804(2) 0.060(2) Uani 1.00 1 d .
C(15) C 0.9234(6) 0.6822(2) 0.4266(2) 0.0497(19) Uani 1.00 1 d .
C(16) C 0.8427(6) 0.7148(2) 0.3836(2) 0.0473(18) Uani 1.00 1 d .
C(17) C 0.7497(7) 0.7595(2) 0.3926(2) 0.067(2) Uani 1.00 1 d .
C(18) C 0.8692(6) 0.6901(2) 0.3296(2) 0.0478(19) Uani 1.00 1 d .
C(19) C 0.7631(6) 0.6705(2) 0.2982(2) 0.056(2) Uani 1.00 1 d .
C(20) C 0.7843(7) 0.6461(2) 0.2483(2) 0.061(2) Uani 1.00 1 d .
C(21) C 0.9151(8) 0.6413(2) 0.2307(2) 0.059(2) Uani 1.00 1 d .
C(22) C 1.0220(7) 0.6616(2) 0.2606(2) 0.057(2) Uani 1.00 1 d .
C(23) C 0.9983(7) 0.6859(2) 0.3097(2) 0.055(2) Uani 1.00 1 d .
C(24) C 0.6798(6) 0.3055(3) 0.3991(3) 0.062(2) Uani 1.00 1 d .
C(25) C 0.7483(7) 0.2696(3) 0.3610(4) 0.079(2) Uani 1.00 1 d .
C(26) C 0.7608(7) 0.2933(3) 0.3116(3) 0.076(2) Uani 1.00 1 d .
C(27) C 0.7096(7) 0.3540(3) 0.2976(2) 0.068(2) Uani 1.00 1 d .
C(28) C 0.7172(7) 0.3791(4) 0.2460(3) 0.083(3) Uani 1.00 1 d .
C(29) C 0.6689(8) 0.4383(4) 0.2335(2) 0.087(2) Uani 1.00 1 d .
C(30) C 0.6079(6) 0.4768(3) 0.2732(2) 0.065(2) Uani 1.00 1 d .
C(31) C 0.5964(6) 0.4539(3) 0.3230(2) 0.056(2) Uani 1.00 1 d .
C(32) C 0.6466(6) 0.3919(3) 0.3371(2) 0.053(2) Uani 1.00 1 d .
C(33) C 0.6317(6) 0.3668(2) 0.3886(2) 0.056(2) Uani 1.00 1 d .
C(34) C 0.5628(6) 0.4048(2) 0.4318(2) 0.0492(18) Uani 1.00 1 d .
C(35) C 0.4183(8) 0.4099(2) 0.4219(2) 0.054(2) Uani 1.00 1 d .
C(36) C 0.3019(8) 0.4129(3) 0.4162(2) 0.063(2) Uani 1.00 1 d .
C(37) C 0.5727(8) 0.3020(3) 0.4814(2) 0.072(2) Uani 1.00 1 d .
C(38) C 0.5894(7) 0.3740(2) 0.4863(2) 0.056(2) Uani 1.00 1 d .
C(39) C 0.5045(7) 0.4043(3) 0.5286(2) 0.059(2) Uani 1.00 1 d .
C(40) C 0.4021(8) 0.3742(3) 0.5501(2) 0.074(2) Uani 1.00 1 d .
C(41) C 0.5410(7) 0.4710(3) 0.5444(2) 0.053(2) Uani 1.00 1 d .
C(42) C 0.4442(7) 0.5191(3) 0.5452(2) 0.064(2) Uani 1.00 1 d .
C(43) C 0.4753(8) 0.5807(3) 0.5601(2) 0.072(2) Uani 1.00 1 d .
C(44) C 0.6053(8) 0.5948(3) 0.5744(2) 0.061(2) Uani 1.00 1 d .
C(45) C 0.7038(7) 0.5480(3) 0.5745(2) 0.062(2) Uani 1.00 1 d .
C(46) C 0.6721(7) 0.4866(3) 0.5587(2) 0.059(2) Uani 1.00 1 d .
C(47) C 0.3235(6) 0.5706(2) 0.2265(2) 0.0489(19) Uani 1.00 1 d .
C(48) C 0.3888(6) 0.6293(2) 0.2178(2) 0.054(2) Uani 1.00 1 d .
C(49) C 0.4099(6) 0.6699(2) 0.2587(2) 0.058(2) Uani 1.00 1 d .
C(50) C 0.3669(6) 0.6545(2) 0.3103(2) 0.0490(19) Uani 1.00 1 d .
C(51) C 0.3820(7) 0.6975(3) 0.3527(2) 0.064(2) Uani 1.00 1 d .
C(52) C 0.3382(7) 0.6815(3) 0.4013(2) 0.063(2) Uani 1.00 1 d .
C(53) C 0.2771(6) 0.6217(3) 0.4108(2) 0.058(2) Uani 1.00 1 d .
C(54) C 0.2604(6) 0.5787(2) 0.3705(2) 0.0498(19) Uani 1.00 1 d .
C(55) C 0.3039(5) 0.5940(2) 0.3192(2) 0.0422(17) Uani 1.00 1 d .
C(56) C 0.2848(5) 0.5509(2) 0.2754(2) 0.0433(17) Uani 1.00 1 d .
C(57) C 0.2209(6) 0.4846(2) 0.2836(2) 0.0440(18) Uani 1.00 1 d .
C(58) C 0.0778(8) 0.4908(2) 0.2944(2) 0.050(2) Uani 1.00 1 d .
C(59) C -0.0379(9) 0.4953(3) 0.3014(2) 0.062(2) Uani 1.00 1 d .
C(60) C 0.2136(6) 0.4824(2) 0.1862(2) 0.055(2) Uani 1.00 1 d .
C(61) C 0.2471(6) 0.4424(2) 0.2347(2) 0.0449(18) Uani 1.00 1 d .
C(62) C 0.1723(6) 0.3796(2) 0.2383(2) 0.0475(18) Uani 1.00 1 d .
C(63) C 0.0730(7) 0.3643(2) 0.2064(2) 0.061(2) Uani 1.00 1 d .
C(64) C 0.2132(6) 0.3357(2) 0.2808(2) 0.0464(18) Uani 1.00 1 d .
C(65) C 0.1179(6) 0.3103(2) 0.3154(2) 0.055(2) Uani 1.00 1 d .
C(66) C 0.1524(7) 0.2684(2) 0.3553(2) 0.059(2) Uani 1.00 1 d .
C(67) C 0.2846(8) 0.2500(2) 0.3595(2) 0.056(2) Uani 1.00 1 d .
C(68) C 0.3819(7) 0.2745(2) 0.3272(2) 0.053(2) Uani 1.00 1 d .
C(69) C 0.3462(7) 0.3174(2) 0.2874(2) 0.0493(19) Uani 1.00 1 d .
H(1) H 1.0888 0.6171 0.5908 0.078 Uiso 1.00 1 c R
H(2) H 1.1119 0.5068 0.5971 0.081 Uiso 1.00 1 c R
H(3) H 1.0849 0.3974 0.5601 0.086 Uiso 1.00 1 c R
H(4) H 1.0115 0.3320 0.4941 0.087 Uiso 1.00 1 c R
H(5) H 0.9259 0.3753 0.4155 0.074 Uiso 1.00 1 c R
H(6) H 0.8938 0.4862 0.4087 0.065 Uiso 1.00 1 c R
H(7) H 0.9334 0.5901 0.3987 0.054 Uiso 1.00 1 c R
H(8) H 0.5391 0.5788 0.4266 0.078 Uiso 1.00 1 c R
H(9) H 0.8081 0.7005 0.4906 0.071 Uiso 1.00 1 c R
H(10) H 0.9090 0.7556 0.4790 0.071 Uiso 1.00 1 c R
H(11) H 1.0157 0.6877 0.4188 0.060 Uiso 1.00 1 c R
H(12) H 0.7308 0.7728 0.4276 0.080 Uiso 1.00 1 c R
H(13) H 0.7023 0.7782 0.3640 0.080 Uiso 1.00 1 c R
H(14) H 0.6743 0.6739 0.3113 0.067 Uiso 1.00 1 c R
H(15) H 0.7114 0.6331 0.2268 0.074 Uiso 1.00 1 c R
H(16) H 1.1107 0.6588 0.2473 0.068 Uiso 1.00 1 c R
H(17) H 1.0715 0.7001 0.3306 0.066 Uiso 1.00 1 c R
H(18) H 0.7856 0.2288 0.3698 0.095 Uiso 1.00 1 c R
H(19) H 0.8054 0.2681 0.2858 0.091 Uiso 1.00 1 c R
H(20) H 0.7574 0.3537 0.2193 0.099 Uiso 1.00 1 c R
H(21) H 0.6759 0.4540 0.1985 0.104 Uiso 1.00 1 c R
H(22) H 0.5750 0.5185 0.2648 0.078 Uiso 1.00 1 c R
H(23) H 0.5541 0.4797 0.3490 0.067 Uiso 1.00 1 c R
H(24) H 0.5992 0.4471 0.4320 0.059 Uiso 1.00 1 c R
H(25) H 0.2076 0.4153 0.4115 0.075 Uiso 1.00 1 c R
H(26) H 0.4858 0.2929 0.4682 0.087 Uiso 1.00 1 c R
H(27) H 0.5825 0.2830 0.5152 0.087 Uiso 1.00 1 c R
H(28) H 0.6804 0.3821 0.4950 0.067 Uiso 1.00 1 c R
H(29) H 0.3509 0.3949 0.5767 0.089 Uiso 1.00 1 c R
H(30) H 0.3795 0.3318 0.5391 0.089 Uiso 1.00 1 c R
H(31) H 0.3548 0.5090 0.5354 0.076 Uiso 1.00 1 c R
H(32) H 0.4084 0.6132 0.5605 0.086 Uiso 1.00 1 c R
H(33) H 0.7924 0.5581 0.5853 0.074 Uiso 1.00 1 c R
H(34) H 0.7399 0.4545 0.5575 0.071 Uiso 1.00 1 c R
H(35) H 0.4181 0.6406 0.1835 0.065 Uiso 1.00 1 c R
H(36) H 0.4546 0.7096 0.2526 0.069 Uiso 1.00 1 c R
H(37) H 0.4234 0.7382 0.3472 0.077 Uiso 1.00 1 c R
H(38) H 0.3489 0.7112 0.4294 0.075 Uiso 1.00 1 c R
H(39) H 0.2473 0.6110 0.4452 0.070 Uiso 1.00 1 c R
H(40) H 0.2191 0.5383 0.3771 0.060 Uiso 1.00 1 c R
H(41) H 0.2624 0.4648 0.3131 0.053 Uiso 1.00 1 c R
H(42) H -0.1317 0.4990 0.3070 0.074 Uiso 1.00 1 c R
H(43) H 0.1249 0.4985 0.1893 0.066 Uiso 1.00 1 c R
H(44) H 0.2201 0.4560 0.1559 0.066 Uiso 1.00 1 c R
H(45) H 0.3401 0.4329 0.2337 0.054 Uiso 1.00 1 c R
H(46) H 0.0286 0.3240 0.2101 0.073 Uiso 1.00 1 c R
H(47) H 0.0459 0.3935 0.1797 0.073 Uiso 1.00 1 c R
H(48) H 0.0267 0.3223 0.3114 0.066 Uiso 1.00 1 c R
H(49) H 0.0868 0.2526 0.3791 0.071 Uiso 1.00 1 c R
H(50) H 0.4728 0.2622 0.3318 0.063 Uiso 1.00 1 c R
H(51) H 0.4131 0.3343 0.2648 0.059 Uiso 1.00 1 c R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.148 0.159
;
International Tables for Crystallography
(1992, 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
C(1) O(1) C(14) 114.7(4) yes
C(24) O(2) C(37) 113.9(5) yes
C(47) O(3) C(60) 114.9(4) yes
O(1) C(1) C(2) 114.1(5) yes
O(1) C(1) C(10) 124.4(5) yes
C(2) C(1) C(10) 121.5(5) yes
C(1) C(2) C(3) 119.0(6) yes
C(2) C(3) C(4) 121.8(6) yes
C(3) C(4) C(5) 121.8(6) yes
C(3) C(4) C(9) 119.4(6) yes
C(5) C(4) C(9) 118.8(6) yes
C(4) C(5) C(6) 120.7(6) yes
C(5) C(6) C(7) 121.5(6) yes
C(6) C(7) C(8) 118.9(6) yes
C(7) C(8) C(9) 121.2(5) yes
C(4) C(9) C(8) 118.8(5) yes
C(4) C(9) C(10) 118.7(5) yes
C(8) C(9) C(10) 122.5(5) yes
C(1) C(10) C(9) 119.5(5) yes
C(1) C(10) C(11) 120.3(5) yes
C(9) C(10) C(11) 120.2(4) yes
C(10) C(11) C(12) 111.2(4) yes
C(10) C(11) C(15) 110.7(4) yes
C(12) C(11) C(15) 111.6(5) yes
C(11) C(12) C(13) 178.3(6) yes
O(1) C(14) C(15) 110.7(5) yes
C(11) C(15) C(14) 108.2(4) yes
C(11) C(15) C(16) 111.2(4) yes
C(14) C(15) C(16) 113.0(4) yes
C(15) C(16) C(17) 123.8(5) yes
C(15) C(16) C(18) 114.7(4) yes
C(17) C(16) C(18) 121.4(5) yes
C(16) C(18) C(19) 119.7(5) yes
C(16) C(18) C(23) 121.5(5) yes
C(19) C(18) C(23) 118.9(5) yes
C(18) C(19) C(20) 121.2(6) yes
C(19) C(20) C(21) 117.9(6) yes
Cl(1) C(21) C(20) 118.8(5) yes
Cl(1) C(21) C(22) 119.2(5) yes
C(20) C(21) C(22) 122.1(5) yes
C(21) C(22) C(23) 118.9(6) yes
C(18) C(23) C(22) 121.0(6) yes
O(2) C(24) C(25) 113.1(6) yes
O(2) C(24) C(33) 125.2(6) yes
C(25) C(24) C(33) 121.7(7) yes
C(24) C(25) C(26) 119.5(7) yes
C(25) C(26) C(27) 121.8(7) yes
C(26) C(27) C(28) 123.1(7) yes
C(26) C(27) C(32) 118.4(6) yes
C(28) C(27) C(32) 118.4(7) yes
C(27) C(28) C(29) 122.2(7) yes
C(28) C(29) C(30) 119.5(7) yes
C(29) C(30) C(31) 120.2(6) yes
C(30) C(31) C(32) 121.3(5) yes
C(27) C(32) C(31) 118.4(5) yes
C(27) C(32) C(33) 119.8(5) yes
C(31) C(32) C(33) 121.8(5) yes
C(24) C(33) C(32) 118.6(6) yes
C(24) C(33) C(34) 119.6(5) yes
C(32) C(33) C(34) 121.8(5) yes
C(33) C(34) C(35) 111.0(5) yes
C(33) C(34) C(38) 111.0(4) yes
C(35) C(34) C(38) 110.7(5) yes
C(34) C(35) C(36) 176.9(6) yes
O(2) C(37) C(38) 111.4(5) yes
C(34) C(38) C(37) 108.3(4) yes
C(34) C(38) C(39) 111.8(5) yes
C(37) C(38) C(39) 114.2(5) yes
C(38) C(39) C(40) 122.4(6) yes
C(38) C(39) C(41) 116.3(5) yes
C(40) C(39) C(41) 121.2(6) yes
C(39) C(41) C(42) 120.1(6) yes
C(39) C(41) C(46) 121.1(6) yes
C(42) C(41) C(46) 118.8(6) yes
C(41) C(42) C(43) 121.1(7) yes
C(42) C(43) C(44) 119.0(7) yes
Cl(2) C(44) C(43) 119.8(5) yes
Cl(2) C(44) C(45) 118.8(6) yes
C(43) C(44) C(45) 121.4(6) yes
C(44) C(45) C(46) 119.2(6) yes
C(41) C(46) C(45) 120.5(6) yes
O(3) C(47) C(48) 113.2(5) yes
O(3) C(47) C(56) 124.4(4) yes
C(48) C(47) C(56) 122.4(5) yes
C(47) C(48) C(49) 119.5(5) yes
C(48) C(49) C(50) 121.6(5) yes
C(49) C(50) C(51) 122.3(5) yes
C(49) C(50) C(55) 118.7(5) yes
C(51) C(50) C(55) 119.0(5) yes
C(50) C(51) C(52) 120.7(5) yes
C(51) C(52) C(53) 121.0(6) yes
C(52) C(53) C(54) 120.0(5) yes
C(53) C(54) C(55) 120.6(5) yes
C(50) C(55) C(54) 118.8(5) yes
C(50) C(55) C(56) 118.9(5) yes
C(54) C(55) C(56) 122.3(5) yes
C(47) C(56) C(55) 118.8(4) yes
C(47) C(56) C(57) 120.8(4) yes
C(55) C(56) C(57) 120.4(4) yes
C(56) C(57) C(58) 110.8(4) yes
C(56) C(57) C(61) 109.2(4) yes
C(58) C(57) C(61) 111.5(4) yes
C(57) C(58) C(59) 177.8(6) yes
O(3) C(60) C(61) 110.6(4) yes
C(57) C(61) C(60) 107.9(4) yes
C(57) C(61) C(62) 111.0(4) yes
C(60) C(61) C(62) 114.3(4) yes
C(61) C(62) C(63) 122.9(5) yes
C(61) C(62) C(64) 116.3(5) yes
C(63) C(62) C(64) 120.8(5) yes
C(62) C(64) C(65) 120.4(5) yes
C(62) C(64) C(69) 121.5(5) yes
C(65) C(64) C(69) 118.0(5) yes
C(64) C(65) C(66) 122.0(6) yes
C(65) C(66) C(67) 118.1(6) yes
Cl(3) C(67) C(66) 119.3(5) yes
Cl(3) C(67) C(68) 118.8(5) yes
C(66) C(67) C(68) 121.9(5) yes
C(67) C(68) C(69) 119.4(6) yes
C(64) C(69) C(68) 120.4(5) yes
C(1) C(2) H(1) 120.5 no
C(3) C(2) H(1) 120.5 no
C(2) C(3) H(2) 119.1 no
C(4) C(3) H(2) 119.1 no
C(4) C(5) H(3) 119.7 no
C(6) C(5) H(3) 119.7 no
C(5) C(6) H(4) 119.2 no
C(7) C(6) H(4) 119.2 no
C(6) C(7) H(5) 120.5 no
C(8) C(7) H(5) 120.5 no
C(7) C(8) H(6) 119.4 no
C(9) C(8) H(6) 119.4 no
C(10) C(11) H(7) 107.7 no
C(12) C(11) H(7) 107.7 no
C(15) C(11) H(7) 107.7 no
C(12) C(13) H(8) 180.0 no
O(1) C(14) H(9) 109.2 no
O(1) C(14) H(10) 109.2 no
C(15) C(14) H(9) 109.2 no
C(15) C(14) H(10) 109.2 no
H(9) C(14) H(10) 109.5 no
C(11) C(15) H(11) 108.1 no
C(14) C(15) H(11) 108.1 no
C(16) C(15) H(11) 108.1 no
C(16) C(17) H(12) 120.0 no
C(16) C(17) H(13) 120.0 no
H(12) C(17) H(13) 120.0 no
C(18) C(19) H(14) 119.4 no
C(20) C(19) H(14) 119.4 no
C(19) C(20) H(15) 121.0 no
C(21) C(20) H(15) 121.0 no
C(21) C(22) H(16) 120.5 no
C(23) C(22) H(16) 120.5 no
C(18) C(23) H(17) 119.5 no
C(22) C(23) H(17) 119.5 no
C(24) C(25) H(18) 120.2 no
C(26) C(25) H(18) 120.2 no
C(25) C(26) H(19) 119.1 no
C(27) C(26) H(19) 119.1 no
C(27) C(28) H(20) 118.9 no
C(29) C(28) H(20) 118.9 no
C(28) C(29) H(21) 120.3 no
C(30) C(29) H(21) 120.3 no
C(29) C(30) H(22) 119.9 no
C(31) C(30) H(22) 119.9 no
C(30) C(31) H(23) 119.4 no
C(32) C(31) H(23) 119.4 no
C(33) C(34) H(24) 108.0 no
C(35) C(34) H(24) 108.0 no
C(38) C(34) H(24) 108.0 no
C(35) C(36) H(25) 180.0 no
O(2) C(37) H(26) 109.0 no
O(2) C(37) H(27) 109.0 no
C(38) C(37) H(26) 109.0 no
C(38) C(37) H(27) 109.0 no
H(26) C(37) H(27) 109.5 no
C(34) C(38) H(28) 107.4 no
C(37) C(38) H(28) 107.4 no
C(39) C(38) H(28) 107.4 no
C(39) C(40) H(29) 120.0 no
C(39) C(40) H(30) 120.0 no
H(29) C(40) H(30) 120.0 no
C(41) C(42) H(31) 119.5 no
C(43) C(42) H(31) 119.5 no
C(42) C(43) H(32) 120.5 no
C(44) C(43) H(32) 120.5 no
C(44) C(45) H(33) 120.4 no
C(46) C(45) H(33) 120.4 no
C(41) C(46) H(34) 119.7 no
C(45) C(46) H(34) 119.7 no
C(47) C(48) H(35) 120.3 no
C(49) C(48) H(35) 120.3 no
C(48) C(49) H(36) 119.2 no
C(50) C(49) H(36) 119.2 no
C(50) C(51) H(37) 119.7 no
C(52) C(51) H(37) 119.7 no
C(51) C(52) H(38) 119.5 no
C(53) C(52) H(38) 119.5 no
C(52) C(53) H(39) 120.0 no
C(54) C(53) H(39) 120.0 no
C(53) C(54) H(40) 119.7 no
C(55) C(54) H(40) 119.7 no
C(56) C(57) H(41) 108.4 no
C(58) C(57) H(41) 108.4 no
C(61) C(57) H(41) 108.4 no
C(58) C(59) H(42) 180.0 no
O(3) C(60) H(43) 109.2 no
O(3) C(60) H(44) 109.2 no
C(61) C(60) H(43) 109.2 no
C(61) C(60) H(44) 109.2 no
H(43) C(60) H(44) 109.5 no
C(57) C(61) H(45) 107.8 no
C(60) C(61) H(45) 107.8 no
C(62) C(61) H(45) 107.8 no
C(62) C(63) H(46) 120.0 no
C(62) C(63) H(47) 120.0 no
H(46) C(63) H(47) 120.0 no
C(64) C(65) H(48) 119.0 no
C(66) C(65) H(48) 119.0 no
C(65) C(66) H(49) 120.9 no
C(67) C(66) H(49) 120.9 no
C(67) C(68) H(50) 120.3 no
C(69) C(68) H(50) 120.3 no
C(64) C(69) H(51) 119.8 no
C(68) C(69) H(51) 119.8 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl(1) C(21) 1.748(6) yes
Cl(2) C(44) 1.751(6) yes
Cl(3) C(67) 1.748(6) yes
O(1) C(1) 1.385(7) yes
O(1) C(14) 1.439(7) yes
O(2) C(24) 1.369(9) yes
O(2) C(37) 1.440(9) yes
O(3) C(47) 1.379(7) yes
O(3) C(60) 1.427(7) yes
C(1) C(2) 1.421(9) yes
C(1) C(10) 1.358(8) yes
C(2) C(3) 1.361(10) yes
C(3) C(4) 1.395(9) yes
C(4) C(5) 1.422(10) yes
C(4) C(9) 1.416(9) yes
C(5) C(6) 1.346(10) yes
C(6) C(7) 1.405(10) yes
C(7) C(8) 1.381(8) yes
C(8) C(9) 1.409(8) yes
C(9) C(10) 1.434(8) yes
C(10) C(11) 1.511(7) yes
C(11) C(12) 1.458(10) yes
C(11) C(15) 1.541(7) yes
C(12) C(13) 1.193(12) yes
C(14) C(15) 1.508(7) yes
C(15) C(16) 1.518(8) yes
C(16) C(17) 1.333(9) yes
C(16) C(18) 1.492(7) yes
C(18) C(19) 1.387(9) yes
C(18) C(23) 1.387(9) yes
C(19) C(20) 1.383(9) yes
C(20) C(21) 1.384(11) yes
C(21) C(22) 1.376(10) yes
C(22) C(23) 1.370(8) yes
C(24) C(25) 1.400(11) yes
C(24) C(33) 1.385(8) yes
C(25) C(26) 1.356(13) yes
C(26) C(27) 1.405(11) yes
C(27) C(28) 1.413(11) yes
C(27) C(32) 1.424(9) yes
C(28) C(29) 1.358(13) yes
C(29) C(30) 1.424(10) yes
C(30) C(31) 1.360(9) yes
C(31) C(32) 1.426(8) yes
C(32) C(33) 1.418(8) yes
C(33) C(34) 1.518(8) yes
C(34) C(35) 1.469(10) yes
C(34) C(38) 1.549(7) yes
C(35) C(36) 1.173(12) yes
C(37) C(38) 1.509(8) yes
C(38) C(39) 1.506(8) yes
C(39) C(40) 1.318(10) yes
C(39) C(41) 1.486(9) yes
C(41) C(42) 1.389(10) yes
C(41) C(46) 1.397(10) yes
C(42) C(43) 1.368(10) yes
C(43) C(44) 1.380(11) yes
C(44) C(45) 1.382(10) yes
C(45) C(46) 1.371(9) yes
C(47) C(48) 1.400(8) yes
C(47) C(56) 1.364(8) yes
C(48) C(49) 1.354(8) yes
C(49) C(50) 1.418(8) yes
C(50) C(51) 1.409(8) yes
C(50) C(55) 1.421(7) yes
C(51) C(52) 1.354(9) yes
C(52) C(53) 1.403(9) yes
C(53) C(54) 1.369(8) yes
C(54) C(55) 1.414(8) yes
C(55) C(56) 1.442(7) yes
C(56) C(57) 1.530(7) yes
C(57) C(58) 1.461(10) yes
C(57) C(61) 1.543(7) yes
C(58) C(59) 1.173(12) yes
C(60) C(61) 1.525(7) yes
C(61) C(62) 1.505(7) yes
C(62) C(63) 1.321(9) yes
C(62) C(64) 1.472(8) yes
C(64) C(65) 1.400(8) yes
C(64) C(69) 1.391(9) yes
C(65) C(66) 1.379(8) yes
C(66) C(67) 1.378(10) yes
C(67) C(68) 1.371(9) yes
C(68) C(69) 1.394(8) yes
C(2) H(1) 0.950 no
C(3) H(2) 0.950 no
C(5) H(3) 0.950 no
C(6) H(4) 0.950 no
C(7) H(5) 0.950 no
C(8) H(6) 0.950 no
C(11) H(7) 0.950 no
C(13) H(8) 0.950 no
C(14) H(9) 0.950 no
C(14) H(10) 0.950 no
C(15) H(11) 0.950 no
C(17) H(12) 0.950 no
C(17) H(13) 0.950 no
C(19) H(14) 0.950 no
C(20) H(15) 0.950 no
C(22) H(16) 0.950 no
C(23) H(17) 0.950 no
C(25) H(18) 0.950 no
C(26) H(19) 0.950 no
C(28) H(20) 0.950 no
C(29) H(21) 0.950 no
C(30) H(22) 0.950 no
C(31) H(23) 0.950 no
C(34) H(24) 0.950 no
C(36) H(25) 0.950 no
C(37) H(26) 0.950 no
C(37) H(27) 0.950 no
C(38) H(28) 0.950 no
C(40) H(29) 0.950 no
C(40) H(30) 0.950 no
C(42) H(31) 0.950 no
C(43) H(32) 0.950 no
C(45) H(33) 0.950 no
C(46) H(34) 0.950 no
C(48) H(35) 0.950 no
C(49) H(36) 0.950 no
C(51) H(37) 0.950 no
C(52) H(38) 0.950 no
C(53) H(39) 0.950 no
C(54) H(40) 0.950 no
C(57) H(41) 0.950 no
C(59) H(42) 0.950 no
C(60) H(43) 0.950 no
C(60) H(44) 0.950 no
C(61) H(45) 0.950 no
C(63) H(46) 0.950 no
C(63) H(47) 0.950 no
C(65) H(48) 0.950 no
C(66) H(49) 0.950 no
C(68) H(50) 0.950 no
C(69) H(51) 0.950 no
