#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:57:32 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180162 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/58/7105875.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_7105875
loop_
_publ_author_name
'Haruo Aikawa'
'Yusuke Takahira'
'Masahiko Yamaguchi'
_publ_section_title
;
 Synthesis of Chiral 1,8-di(1-adamantyl)naphthalenes Stable at Ambient
 Temperatures
;
_journal_name_full               Chem.Commun.
_journal_page_first              1479
_journal_paper_doi               10.1039/c0cc03025b
_journal_volume                  47
_journal_year                    2011
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C42 H52 Cl2 O4'
_chemical_formula_weight         691.74
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.547(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.664(4)
_cell_length_b                   12.144(4)
_cell_length_c                   14.023(5)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      2.25
_cell_volume                     1765.5(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material
'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SHELXD
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19483
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.9777
_exptl_absorpt_correction_T_min  0.9561
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS (Sheldrick, 1997)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             740
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.778
_refine_diff_density_min         -0.757
_refine_diff_density_rms         0.113
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(9)
_refine_ls_extinction_coef       0.039(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         7942
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0587
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0990P)²+0.7158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1578
_refine_ls_wR_factor_ref         0.1598
_reflns_number_gt                7694
_reflns_number_total             7942
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC03025B.TXT
_cod_data_source_block           100127
_cod_original_cell_volume        1765.6(11)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7105875
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7529(2) 0.06351(16) 0.17240(15) 0.0170(4) Uani 1 1 d . . .
C2 C 0.8827(2) 0.04754(18) 0.18086(17) 0.0213(4) Uani 1 1 d . . .
H1 H 0.9082 -0.0095 0.1431 0.026 Uiso 1 1 calc R . .
C3 C 0.9798(2) 0.11008(19) 0.24167(17) 0.0226(4) Uani 1 1 d . . .
H2 H 1.0675 0.0879 0.2532 0.027 Uiso 1 1 calc R . .
C4 C 0.9464(2) 0.20326(18) 0.28399(16) 0.0190(4) Uani 1 1 d . . .
C5 C 0.7679(2) 0.31727(17) 0.32506(14) 0.0161(4) Uani 1 1 d . . .
C6 C 0.6431(2) 0.32760(17) 0.33115(15) 0.0184(4) Uani 1 1 d . . .
H3 H 0.6110 0.3962 0.3478 0.022 Uiso 1 1 calc R . .
C7 C 0.5627(2) 0.23475(18) 0.31240(16) 0.0195(4) Uani 1 1 d . . .
H4 H 0.4786 0.2394 0.3240 0.023 Uiso 1 1 calc R . .
C8 C 0.60096(19) 0.13732(17) 0.27789(15) 0.0161(4) Uani 1 1 d . . .
C9 C 0.71912(19) 0.13835(16) 0.24363(14) 0.0151(4) Uani 1 1 d . . .
C10 C 0.81277(19) 0.22191(16) 0.28453(14) 0.0153(4) Uani 1 1 d . . .
C11 C 0.66274(19) 0.02904(17) 0.07281(15) 0.0161(4) Uani 1 1 d . . .
C12 C 0.7068(2) 0.10025(18) -0.00666(17) 0.0222(4) Uani 1 1 d . . .
H5 H 0.6966 0.1793 0.0072 0.027 Uiso 1 1 calc R . .
H6 H 0.7993 0.0864 -0.0030 0.027 Uiso 1 1 calc R . .
C13 C 0.6787(2) -0.09300(17) 0.04646(15) 0.0180(4) Uani 1 1 d . . .
H7 H 0.7707 -0.1085 0.0497 0.022 Uiso 1 1 calc R . .
H8 H 0.6508 -0.1410 0.0947 0.022 Uiso 1 1 calc R . .
C14 C 0.5192(2) 0.05592(19) 0.06164(16) 0.0204(4) Uani 1 1 d . . .
H9 H 0.4858 0.0137 0.1108 0.025 Uiso 1 1 calc R . .
H10 H 0.5096 0.1353 0.0745 0.025 Uiso 1 1 calc R . .
C15 C 0.6281(2) 0.0734(2) -0.11049(17) 0.0261(5) Uani 1 1 d . . .
H11 H 0.6596 0.1196 -0.1592 0.031 Uiso 1 1 calc R . .
C16 C 0.6448(2) -0.0484(2) -0.13239(17) 0.0272(5) Uani 1 1 d . . .
H12 H 0.7368 -0.0642 -0.1292 0.033 Uiso 1 1 calc R . .
H13 H 0.5944 -0.0663 -0.1993 0.033 Uiso 1 1 calc R . .
C17 C 0.5981(2) -0.11900(18) -0.05707(16) 0.0222(4) Uani 1 1 d . . .
H14 H 0.6085 -0.1986 -0.0718 0.027 Uiso 1 1 calc R . .
C18 C 0.4558(2) -0.0952(2) -0.06226(16) 0.0243(4) Uani 1 1 d . . .
H15 H 0.4259 -0.1405 -0.0132 0.029 Uiso 1 1 calc R . .
H16 H 0.4031 -0.1144 -0.1281 0.029 Uiso 1 1 calc R . .
C19 C 0.4397(2) 0.0276(2) -0.04167(16) 0.0228(4) Uani 1 1 d . . .
H17 H 0.3467 0.0435 -0.0455 0.027 Uiso 1 1 calc R . .
C20 C 0.4855(3) 0.0975(2) -0.11814(18) 0.0280(5) Uani 1 1 d . . .
H18 H 0.4345 0.0793 -0.1848 0.034 Uiso 1 1 calc R . .
H19 H 0.4734 0.1767 -0.1060 0.034 Uiso 1 1 calc R . .
C21 C 0.5351(2) 0.03184(17) 0.30652(15) 0.0164(4) Uani 1 1 d . . .
C22 C 0.5931(2) -0.07782(17) 0.28166(15) 0.0180(4) Uani 1 1 d . . .
H20 H 0.5792 -0.0847 0.2096 0.022 Uiso 1 1 calc R . .
H21 H 0.6872 -0.0779 0.3103 0.022 Uiso 1 1 calc R . .
C23 C 0.3871(2) 0.03080(18) 0.26870(16) 0.0204(4) Uani 1 1 d . . .
H22 H 0.3506 0.0994 0.2892 0.024 Uiso 1 1 calc R . .
H23 H 0.3648 0.0281 0.1961 0.024 Uiso 1 1 calc R . .
C24 C 0.5634(2) 0.03459(19) 0.42112(16) 0.0224(4) Uani 1 1 d . . .
H24 H 0.6578 0.0342 0.4483 0.027 Uiso 1 1 calc R . .
H25 H 0.5286 0.1036 0.4422 0.027 Uiso 1 1 calc R . .
C25 C 0.5316(2) -0.17659(18) 0.32142(17) 0.0222(4) Uani 1 1 d . . .
H26 H 0.5684 -0.2463 0.3014 0.027 Uiso 1 1 calc R . .
C26 C 0.3849(2) -0.1749(2) 0.27868(18) 0.0258(5) Uani 1 1 d . . .
H27 H 0.3665 -0.1794 0.2062 0.031 Uiso 1 1 calc R . .
H28 H 0.3448 -0.2394 0.3030 0.031 Uiso 1 1 calc R . .
C27 C 0.3281(2) -0.0690(2) 0.30923(17) 0.0242(4) Uani 1 1 d . . .
H29 H 0.2326 -0.0691 0.2821 0.029 Uiso 1 1 calc R . .
C28 C 0.3564(2) -0.0631(2) 0.42172(18) 0.0279(5) Uani 1 1 d . . .
H30 H 0.3195 0.0054 0.4422 0.033 Uiso 1 1 calc R . .
H31 H 0.3166 -0.1266 0.4476 0.033 Uiso 1 1 calc R . .
C29 C 0.5028(2) -0.0645(2) 0.46223(16) 0.0256(5) Uani 1 1 d . . .
H32 H 0.5223 -0.0592 0.5354 0.031 Uiso 1 1 calc R . .
C30 C 0.5589(3) -0.1711(2) 0.43330(18) 0.0277(5) Uani 1 1 d . . .
H33 H 0.5191 -0.2350 0.4588 0.033 Uiso 1 1 calc R . .
H34 H 0.6531 -0.1733 0.4616 0.033 Uiso 1 1 calc R . .
C31 C 1.1648(2) 0.2624(2) 0.3301(2) 0.0337(6) Uani 1 1 d . . .
H35 H 1.1948 0.1972 0.3701 0.051 Uiso 1 1 calc R . .
H36 H 1.2161 0.3265 0.3584 0.051 Uiso 1 1 calc R . .
H37 H 1.1745 0.2502 0.2631 0.051 Uiso 1 1 calc R . .
C32 C 0.87269(19) 0.47936(17) 0.29859(15) 0.0167(4) Uani 1 1 d . . .
C33 C 0.9444(2) 0.57668(17) 0.34878(15) 0.0171(4) Uani 1 1 d . . .
C34 C 1.0683(2) 0.55144(18) 0.42970(17) 0.0239(5) Uani 1 1 d . . .
H38 H 1.1190 0.4915 0.4090 0.029 Uiso 1 1 calc R . .
H39 H 1.0464 0.5304 0.4921 0.029 Uiso 1 1 calc R . .
C35 C 1.1439(2) 0.66238(19) 0.44064(18) 0.0270(5) Uani 1 1 d . . .
H40 H 1.1627 0.6892 0.5092 0.032 Uiso 1 1 calc R . .
H41 H 1.2258 0.6548 0.4196 0.032 Uiso 1 1 calc R . .
C36 C 1.0498(2) 0.73959(18) 0.37198(18) 0.0244(5) Uani 1 1 d . . .
H42 H 1.0901 0.8085 0.3540 0.029 Uiso 1 1 calc R . .
C37 C 0.9366(3) 0.75898(19) 0.4203(2) 0.0303(5) Uani 1 1 d . . .
H43 H 0.9673 0.7751 0.4911 0.036 Uiso 1 1 calc R . .
H44 H 0.8811 0.8203 0.3883 0.036 Uiso 1 1 calc R . .
C38 C 0.8650(2) 0.64915(18) 0.40352(17) 0.0232(4) Uani 1 1 d . . .
C39 C 0.9898(2) 0.66434(18) 0.28358(16) 0.0212(4) Uani 1 1 d . . .
C40 C 0.8786(3) 0.7194(2) 0.20947(19) 0.0321(5) Uani 1 1 d . . .
H45 H 0.9057 0.7925 0.1925 0.048 Uiso 1 1 calc R . .
H46 H 0.8038 0.7267 0.2385 0.048 Uiso 1 1 calc R . .
H47 H 0.8552 0.6741 0.1501 0.048 Uiso 1 1 calc R . .
C41 C 1.0879(3) 0.6209(2) 0.2288(2) 0.0316(5) Uani 1 1 d . . .
H48 H 1.0444 0.5719 0.1757 0.047 Uiso 1 1 calc R . .
H49 H 1.1556 0.5800 0.2744 0.047 Uiso 1 1 calc R . .
H50 H 1.1264 0.6829 0.2011 0.047 Uiso 1 1 calc R . .
O1 O 1.03213(15) 0.28178(15) 0.32819(14) 0.0268(4) Uani 1 1 d . . .
O2 O 0.85005(14) 0.40484(12) 0.36455(10) 0.0180(3) Uani 1 1 d . . .
O3 O 0.83752(18) 0.46706(15) 0.21130(12) 0.0294(4) Uani 1 1 d . . .
O4 O 0.7682(2) 0.62509(17) 0.42752(17) 0.0399(5) Uani 1 1 d . . .
C42 C 0.9519(5) 0.3312(5) 0.0615(3) 0.0756(14) Uani 1 1 d . . .
H51 H 0.9962 0.3828 0.1131 0.091 Uiso 1 1 calc R . .
H52 H 0.8857 0.2913 0.0871 0.091 Uiso 1 1 calc R . .
Cl1 Cl 1.06052(13) 0.23941(13) 0.03928(9) 0.0780(4) Uani 1 1 d . . .
Cl2 Cl 0.87486(18) 0.4073(2) -0.04181(14) 0.1211(7) 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9 115.75(18) . . ?
C2 C1 C11 115.94(18) . . ?
C9 C1 C11 125.68(17) . . ?
C1 C2 C3 124.1(2) . . ?
C1 C2 H1 117.9 . . ?
C3 C2 H1 117.9 . . ?
C4 C3 C2 118.97(19) . . ?
C4 C3 H2 120.5 . . ?
C2 C3 H2 120.5 . . ?
C3 C4 O1 124.19(19) . . ?
C3 C4 C10 119.40(19) . . ?
O1 C4 C10 116.40(18) . . ?
C6 C5 O2 115.75(18) . . ?
C6 C5 C10 121.79(18) . . ?
O2 C5 C10 122.42(18) . . ?
C5 C6 C7 118.57(19) . . ?
C5 C6 H3 120.7 . . ?
C7 C6 H3 120.7 . . ?
C8 C7 C6 122.56(19) . . ?
C8 C7 H4 118.7 . . ?
C6 C7 H4 118.7 . . ?
C7 C8 C9 117.48(18) . . ?
C7 C8 C21 115.32(17) . . ?
C9 C8 C21 124.86(17) . . ?
C10 C9 C8 116.62(17) . . ?
C10 C9 C1 116.83(17) . . ?
C8 C9 C1 126.54(18) . . ?
C5 C10 C4 123.70(18) . . ?
C5 C10 C9 117.68(17) . . ?
C4 C10 C9 118.60(18) . . ?
C14 C11 C13 109.98(17) . . ?
C14 C11 C1 115.19(17) . . ?
C13 C11 C1 113.14(16) . . ?
C14 C11 C12 105.54(17) . . ?
C13 C11 C12 106.91(16) . . ?
C1 C11 C12 105.34(16) . . ?
C15 C12 C11 111.65(18) . . ?
C15 C12 H5 109.3 . . ?
C11 C12 H5 109.3 . . ?
C15 C12 H6 109.3 . . ?
C11 C12 H6 109.3 . . ?
H5 C12 H6 108.0 . . ?
C17 C13 C11 110.76(17) . . ?
C17 C13 H7 109.5 . . ?
C11 C13 H7 109.5 . . ?
C17 C13 H8 109.5 . . ?
C11 C13 H8 109.5 . . ?
H7 C13 H8 108.1 . . ?
C19 C14 C11 111.39(18) . . ?
C19 C14 H9 109.3 . . ?
C11 C14 H9 109.3 . . ?
C19 C14 H10 109.3 . . ?
C11 C14 H10 109.3 . . ?
H9 C14 H10 108.0 . . ?
C20 C15 C16 109.4(2) . . ?
C20 C15 C12 109.9(2) . . ?
C16 C15 C12 109.38(19) . . ?
C20 C15 H11 109.4 . . ?
C16 C15 H11 109.4 . . ?
C12 C15 H11 109.4 . . ?
C15 C16 C17 109.32(19) . . ?
C15 C16 H12 109.8 . . ?
C17 C16 H12 109.8 . . ?
C15 C16 H13 109.8 . . ?
C17 C16 H13 109.8 . . ?
H12 C16 H13 108.3 . . ?
C18 C17 C16 109.93(19) . . ?
C18 C17 C13 109.57(18) . . ?
C16 C17 C13 109.68(18) . . ?
C18 C17 H14 109.2 . . ?
C16 C17 H14 109.2 . . ?
C13 C17 H14 109.2 . . ?
C17 C18 C19 109.08(18) . . ?
C17 C18 H15 109.9 . . ?
C19 C18 H15 109.9 . . ?
C17 C18 H16 109.9 . . ?
C19 C18 H16 109.9 . . ?
H15 C18 H16 108.3 . . ?
C20 C19 C14 109.86(19) . . ?
C20 C19 C18 109.78(19) . . ?
C14 C19 C18 109.48(18) . . ?
C20 C19 H17 109.2 . . ?
C14 C19 H17 109.2 . . ?
C18 C19 H17 109.2 . . ?
C15 C20 C19 108.62(19) . . ?
C15 C20 H18 110.0 . . ?
C19 C20 H18 110.0 . . ?
C15 C20 H19 110.0 . . ?
C19 C20 H19 110.0 . . ?
H18 C20 H19 108.3 . . ?
C22 C21 C23 110.33(16) . . ?
C22 C21 C8 115.01(16) . . ?
C23 C21 C8 113.87(17) . . ?
C22 C21 C24 105.05(17) . . ?
C23 C21 C24 106.78(17) . . ?
C8 C21 C24 104.90(16) . . ?
C25 C22 C21 111.41(17) . . ?
C25 C22 H20 109.3 . . ?
C21 C22 H20 109.3 . . ?
C25 C22 H21 109.3 . . ?
C21 C22 H21 109.3 . . ?
H20 C22 H21 108.0 . . ?
C27 C23 C21 110.75(18) . . ?
C27 C23 H22 109.5 . . ?
C21 C23 H22 109.5 . . ?
C27 C23 H23 109.5 . . ?
C21 C23 H23 109.5 . . ?
H22 C23 H23 108.1 . . ?
C29 C24 C21 111.77(17) . . ?
C29 C24 H24 109.3 . . ?
C21 C24 H24 109.3 . . ?
C29 C24 H25 109.3 . . ?
C21 C24 H25 109.3 . . ?
H24 C24 H25 107.9 . . ?
C30 C25 C22 110.16(18) . . ?
C30 C25 C26 109.32(19) . . ?
C22 C25 C26 109.30(18) . . ?
C30 C25 H26 109.4 . . ?
C22 C25 H26 109.4 . . ?
C26 C25 H26 109.4 . . ?
C27 C26 C25 109.65(18) . . ?
C27 C26 H27 109.7 . . ?
C25 C26 H27 109.7 . . ?
C27 C26 H28 109.7 . . ?
C25 C26 H28 109.7 . . ?
H27 C26 H28 108.2 . . ?
C26 C27 C23 109.73(18) . . ?
C26 C27 C28 109.4(2) . . ?
C23 C27 C28 110.11(18) . . ?
C26 C27 H29 109.2 . . ?
C23 C27 H29 109.2 . . ?
C28 C27 H29 109.2 . . ?
C29 C28 C27 108.55(18) . . ?
C29 C28 H30 110.0 . . ?
C27 C28 H30 110.0 . . ?
C29 C28 H31 110.0 . . ?
C27 C28 H31 110.0 . . ?
H30 C28 H31 108.4 . . ?
C30 C29 C28 110.0(2) . . ?
C30 C29 C24 109.83(19) . . ?
C28 C29 C24 109.4(2) . . ?
C30 C29 H32 109.2 . . ?
C28 C29 H32 109.2 . . ?
C24 C29 H32 109.2 . . ?
C29 C30 C25 108.57(19) . . ?
C29 C30 H33 110.0 . . ?
C25 C30 H33 110.0 . . ?
C29 C30 H34 110.0 . . ?
C25 C30 H34 110.0 . . ?
H33 C30 H34 108.4 . . ?
O1 C31 H35 109.5 . . ?
O1 C31 H36 109.5 . . ?
H35 C31 H36 109.5 . . ?
O1 C31 H37 109.5 . . ?
H35 C31 H37 109.5 . . ?
H36 C31 H37 109.5 . . ?
O3 C32 O2 123.28(19) . . ?
O3 C32 C33 125.58(19) . . ?
O2 C32 C33 111.14(17) . . ?
C32 C33 C38 113.97(18) . . ?
C32 C33 C39 117.48(17) . . ?
C38 C33 C39 100.65(17) . . ?
C32 C33 C34 116.19(17) . . ?
C38 C33 C34 102.73(17) . . ?
C39 C33 C34 103.62(17) . . ?
C33 C34 C35 103.44(17) . . ?
C33 C34 H38 111.1 . . ?
C35 C34 H38 111.1 . . ?
C33 C34 H39 111.1 . . ?
C35 C34 H39 111.1 . . ?
H38 C34 H39 109.0 . . ?
C36 C35 C34 102.66(17) . . ?
C36 C35 H40 111.2 . . ?
C34 C35 H40 111.2 . . ?
C36 C35 H41 111.2 . . ?
C34 C35 H41 111.2 . . ?
H40 C35 H41 109.1 . . ?
C37 C36 C35 106.4(2) . . ?
C37 C36 C39 102.88(18) . . ?
C35 C36 C39 103.16(18) . . ?
C37 C36 H42 114.4 . . ?
C35 C36 H42 114.4 . . ?
C39 C36 H42 114.4 . . ?
C38 C37 C36 102.39(19) . . ?
C38 C37 H43 111.3 . . ?
C36 C37 H43 111.3 . . ?
C38 C37 H44 111.3 . . ?
C36 C37 H44 111.3 . . ?
H43 C37 H44 109.2 . . ?
O4 C38 C37 127.2(2) . . ?
O4 C38 C33 127.7(2) . . ?
C37 C38 C33 105.18(19) . . ?
C41 C39 C40 108.7(2) . . ?
C41 C39 C36 113.70(19) . . ?
C40 C39 C36 113.1(2) . . ?
C41 C39 C33 113.80(19) . . ?
C40 C39 C33 113.53(18) . . ?
C36 C39 C33 93.47(17) . . ?
C39 C40 H45 109.5 . . ?
C39 C40 H46 109.5 . . ?
H45 C40 H46 109.5 . . ?
C39 C40 H47 109.5 . . ?
H45 C40 H47 109.5 . . ?
H46 C40 H47 109.5 . . ?
C39 C41 H48 109.5 . . ?
C39 C41 H49 109.5 . . ?
H48 C41 H49 109.5 . . ?
C39 C41 H50 109.5 . . ?
H48 C41 H50 109.5 . . ?
H49 C41 H50 109.5 . . ?
C4 O1 C31 116.66(18) . . ?
C32 O2 C5 115.49(15) . . ?
Cl1 C42 Cl2 113.9(3) . . ?
Cl1 C42 H51 108.8 . . ?
Cl2 C42 H51 108.8 . . ?
Cl1 C42 H52 108.8 . . ?
Cl2 C42 H52 108.8 . . ?
H51 C42 H52 107.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.375(3) . ?
C1 C9 1.457(3) . ?
C1 C11 1.556(3) . ?
C2 C3 1.400(3) . ?
C2 H1 0.9500 . ?
C3 C4 1.363(3) . ?
C3 H2 0.9500 . ?
C4 O1 1.365(3) . ?
C4 C10 1.445(3) . ?
C5 C6 1.359(3) . ?
C5 O2 1.407(2) . ?
C5 C10 1.422(3) . ?
C6 C7 1.404(3) . ?
C6 H3 0.9500 . ?
C7 C8 1.376(3) . ?
C7 H4 0.9500 . ?
C8 C9 1.450(3) . ?
C8 C21 1.558(3) . ?
C9 C10 1.445(3) . ?
C11 C14 1.537(3) . ?
C11 C13 1.546(3) . ?
C11 C12 1.567(3) . ?
C12 C15 1.535(3) . ?
C12 H5 0.9900 . ?
C12 H6 0.9900 . ?
C13 C17 1.536(3) . ?
C13 H7 0.9900 . ?
C13 H8 0.9900 . ?
C14 C19 1.536(3) . ?
C14 H9 0.9900 . ?
C14 H10 0.9900 . ?
C15 C20 1.528(4) . ?
C15 C16 1.531(3) . ?
C15 H11 1.0000 . ?
C16 C17 1.531(3) . ?
C16 H12 0.9900 . ?
C16 H13 0.9900 . ?
C17 C18 1.530(3) . ?
C17 H14 1.0000 . ?
C18 C19 1.537(3) . ?
C18 H15 0.9900 . ?
C18 H16 0.9900 . ?
C19 C20 1.534(3) . ?
C19 H17 1.0000 . ?
C20 H18 0.9900 . ?
C20 H19 0.9900 . ?
C21 C22 1.542(3) . ?
C21 C23 1.543(3) . ?
C21 C24 1.564(3) . ?
C22 C25 1.533(3) . ?
C22 H20 0.9900 . ?
C22 H21 0.9900 . ?
C23 C27 1.535(3) . ?
C23 H22 0.9900 . ?
C23 H23 0.9900 . ?
C24 C29 1.541(3) . ?
C24 H24 0.9900 . ?
C24 H25 0.9900 . ?
C25 C30 1.529(3) . ?
C25 C26 1.539(3) . ?
C25 H26 1.0000 . ?
C26 C27 1.525(3) . ?
C26 H27 0.9900 . ?
C26 H28 0.9900 . ?
C27 C28 1.537(3) . ?
C27 H29 1.0000 . ?
C28 C29 1.531(3) . ?
C28 H30 0.9900 . ?
C28 H31 0.9900 . ?
C29 C30 1.521(4) . ?
C29 H32 1.0000 . ?
C30 H33 0.9900 . ?
C30 H34 0.9900 . ?
C31 O1 1.428(3) . ?
C31 H35 0.9800 . ?
C31 H36 0.9800 . ?
C31 H37 0.9800 . ?
C32 O3 1.203(3) . ?
C32 O2 1.355(2) . ?
C32 C33 1.491(3) . ?
C33 C38 1.544(3) . ?
C33 C39 1.553(3) . ?
C33 C34 1.557(3) . ?
C34 C35 1.559(3) . ?
C34 H38 0.9900 . ?
C34 H39 0.9900 . ?
C35 C36 1.536(3) . ?
C35 H40 0.9900 . ?
C35 H41 0.9900 . ?
C36 C37 1.534(4) . ?
C36 C39 1.552(3) . ?
C36 H42 1.0000 . ?
C37 C38 1.527(3) . ?
C37 H43 0.9900 . ?
C37 H44 0.9900 . ?
C38 O4 1.195(3) . ?
C39 C41 1.530(3) . ?
C39 C40 1.535(3) . ?
C40 H45 0.9800 . ?
C40 H46 0.9800 . ?
C40 H47 0.9800 . ?
C41 H48 0.9800 . ?
C41 H49 0.9800 . ?
C41 H50 0.9800 . ?
C42 Cl1 1.688(6) . ?
C42 Cl2 1.752(6) . ?
C42 H51 0.9900 . ?
C42 H52 0.9900 . ?
