#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/76/7217673.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_7217673
loop_
_publ_author_name
'Huang, Hong-Li'
'Qi, Feng-Ming'
'Yuan, Ji-Cheng'
'Zhao, Cai-Gui'
'Yang, Jing-Wei'
'Fang, Fu-Hu'
'Wu, Quan-xiang'
'Gao, Kun'
'Yuan, Cheng-Shan'
_publ_section_title
;
 Labdane-Type Diterpenoids from Croton laevigatus
;
_journal_name_full               'RSC Advances'
_journal_paper_doi               10.1039/C4RA04863F
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C22 H36 O5,0.5(C H2 Cl2)'
_chemical_formula_sum            'C22.5 H37 Cl O5'
_chemical_formula_weight         422.97
_chemical_melting_point          415.7
_chemical_name_systematic
;
 ?
;
_chemical_optical_rotation       '[\a]^26^~D~=+9.09 (c 0.11, in CHCl3)'
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-07-28
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 129.100(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.328(15)
_cell_length_b                   11.042(7)
_cell_length_c                   19.217(19)
_cell_measurement_reflns_used    2123
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.47
_cell_measurement_theta_min      2.73
_cell_volume                     4335(6)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.1320
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14626
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         2.131
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             1832
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1256 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.30(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     538
_refine_ls_number_reflns         7875
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1511
_refine_ls_R_factor_gt           0.0782
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0440P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1362
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_full    0.951
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                4290
_reflns_number_total             7875
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ra04863f2.cif
_cod_data_source_block           compound_8
_cod_original_cell_volume        4336(6)
_cod_original_formula_sum        'C22.50 H37 Cl O5'
_cod_database_code               7217673
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2014-3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.954
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C37-C36A \\sim C36B-C37B
 with sigma of 0.02
 C36A-C35 \\sim C36B-C35
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uiso(C36A) = Uiso(C36B)
4. Others
 Fixed Sof: C36A(0.83) H36A(0.83) C37(0.83) H37A(0.83) H37B(0.83) C36B(0.17)
 H36B(0.17) C37B(0.17) H37C(0.17) H37D(0.17) Cl1(0.5) C45(0.25) H45(0.5)
 Cl2(0.125) Cl3(0.25) Cl4(0.125)
5.a Riding coordinates:
 C45(H45)
5.b Ternary CH refined with riding coordinates:
 C27(H27), C31(H31), C34(H34), C5(H5), C9(H9), C12(H12)
5.c Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C28(H28A,H28B), C29(H29A,
 H29B), C33(H33A,H33B), C39(H39A,H39B), C40(H40A,H40B), C1(H1A,H1B), C2(H2A,
 H2B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C17(H17A,H17B),
 C18(H18A,H18B)
5.d Aromatic/amide H refined with riding coordinates:
 C36A(H36A), C36B(H36B), C14(H14)
5.e X=CH2 refined with riding coordinates:
 C37(H37A,H37B), C37B(H37C,H37D), C15(H15A,H15B)
5.f Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C44(H44A,H44B,
 H44C), C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,
 H22B,H22C)
5.g Idealised tetrahedral OH refined as rotating group:
 O6(H6), O7(H7), O1(H1), O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O 0.1981(3) 0.9616(4) 0.2185(3) 0.0608(14) Uani 1 1 d . . . . .
H6 H 0.1919 1.0033 0.2477 0.091 Uiso 1 1 calc GR . . . .
O7 O 0.2088(2) 0.0937(4) 0.3476(4) 0.0530(13) Uani 1 1 d . . . . .
H7 H 0.1736 0.0915 0.3376 0.079 Uiso 1 1 calc GR . . . .
O8 O 0.3328(2) 0.3300(4) 0.4375(3) 0.0420(11) Uani 1 1 d . . . . .
O9 O 0.3957(2) 0.3251(4) 0.3625(3) 0.0465(12) Uani 1 1 d . . . . .
O10 O 0.4032(3) 0.4436(6) 0.2761(4) 0.0791(19) Uani 1 1 d . . . . .
C23 C 0.1256(3) 0.5190(6) 0.1903(4) 0.0471(19) Uani 1 1 d . . . . .
H23A H 0.1017 0.4453 0.1592 0.057 Uiso 1 1 calc R . . . .
H23B H 0.1262 0.5287 0.2410 0.057 Uiso 1 1 calc R . . . .
C24 C 0.0902(3) 0.6253(7) 0.1276(5) 0.055(2) Uani 1 1 d . . . . .
H24A H 0.0467 0.6314 0.1100 0.066 Uiso 1 1 calc R . . . .
H24B H 0.0854 0.6120 0.0739 0.066 Uiso 1 1 calc R . . . .
C25 C 0.1269(4) 0.7436(7) 0.1716(5) 0.052(2) Uani 1 1 d . . . . .
H25A H 0.1263 0.7618 0.2205 0.063 Uiso 1 1 calc R . . . .
H25B H 0.1040 0.8085 0.1279 0.063 Uiso 1 1 calc R . . . .
C26 C 0.1984(3) 0.7415(6) 0.2082(4) 0.0409(17) Uani 1 1 d . . . . .
C27 C 0.2317(3) 0.6291(6) 0.2686(4) 0.0351(16) Uani 1 1 d . . . . .
H27 H 0.2284 0.6412 0.3162 0.042 Uiso 1 1 calc R . . . .
C28 C 0.3055(3) 0.6186(6) 0.3183(4) 0.0418(17) Uani 1 1 d . . . . .
H28A H 0.3125 0.5965 0.2761 0.050 Uiso 1 1 calc R . . . .
H28B H 0.3261 0.6965 0.3440 0.050 Uiso 1 1 calc R . . . .
C29 C 0.3370(3) 0.5244(6) 0.3922(4) 0.0447(18) Uani 1 1 d . . . . .
H29A H 0.3329 0.5501 0.4368 0.054 Uiso 1 1 calc R . . . .
H29B H 0.3833 0.5194 0.4213 0.054 Uiso 1 1 calc R . . . .
C30 C 0.3066(3) 0.3994(6) 0.3580(4) 0.0359(17) Uani 1 1 d . . . . .
C31 C 0.2329(3) 0.4106(5) 0.3035(4) 0.0333(16) Uani 1 1 d . . . . .
H31 H 0.2272 0.4413 0.3461 0.040 Uiso 1 1 calc R . . . .
C32 C 0.1973(3) 0.5054(6) 0.2256(4) 0.0360(17) Uani 1 1 d . . . . .
C33 C 0.2037(3) 0.2835(5) 0.2801(4) 0.0378(17) Uani 1 1 d . . . . .
H33A H 0.1565 0.2882 0.2438 0.045 Uiso 1 1 calc R . . . .
H33B H 0.2139 0.2412 0.2460 0.045 Uiso 1 1 calc R . . . .
C34 C 0.2322(3) 0.2159(6) 0.3658(5) 0.0410(18) Uani 1 1 d . . . . .
H34 H 0.2174 0.2564 0.3956 0.049 Uiso 1 1 calc R . . . .
C35 C 0.3069(4) 0.2124(6) 0.4317(4) 0.0431(18) Uani 1 1 d . . . . .
C38 C 0.3350(3) 0.1162(6) 0.4089(4) 0.0490(19) Uani 1 1 d . . . . .
H38A H 0.3127 0.1179 0.3457 0.073 Uiso 1 1 calc GR . . . .
H38B H 0.3293 0.0381 0.4252 0.073 Uiso 1 1 calc GR . . . .
H38C H 0.3808 0.1313 0.4414 0.073 Uiso 1 1 calc GR . . . .
C39 C 0.3257(3) 0.3470(6) 0.3040(4) 0.0385(16) Uani 1 1 d . . . . .
H39A H 0.3024 0.2717 0.2761 0.046 Uiso 1 1 calc R . . . .
H39B H 0.3136 0.4032 0.2570 0.046 Uiso 1 1 calc R . . . .
C40 C 0.2315(4) 0.8523(7) 0.2669(5) 0.058(2) Uani 1 1 d . . . . .
H40A H 0.2323 0.8459 0.3180 0.070 Uiso 1 1 calc R . . . .
H40B H 0.2764 0.8557 0.2894 0.070 Uiso 1 1 calc R . . . .
C41 C 0.2020(3) 0.7497(6) 0.1319(4) 0.050(2) Uani 1 1 d . . . . .
H41A H 0.1751 0.6877 0.0884 0.076 Uiso 1 1 calc GR . . . .
H41B H 0.2465 0.7387 0.1556 0.076 Uiso 1 1 calc GR . . . .
H41C H 0.1868 0.8277 0.1038 0.076 Uiso 1 1 calc GR . . . .
C42 C 0.1947(3) 0.4655(6) 0.1471(4) 0.0449(18) Uani 1 1 d . . . . .
H42A H 0.1887 0.3794 0.1397 0.067 Uiso 1 1 calc GR . . . .
H42B H 0.2349 0.4871 0.1592 0.067 Uiso 1 1 calc GR . . . .
H42C H 0.1588 0.5051 0.0932 0.067 Uiso 1 1 calc GR . . . .
C43 C 0.4291(4) 0.3809(6) 0.3409(5) 0.0430(19) Uani 1 1 d . . . . .
C44 C 0.4999(3) 0.3516(8) 0.4040(4) 0.055(2) Uani 1 1 d . . . . .
H44A H 0.5172 0.3529 0.3725 0.082 Uiso 1 1 calc GR . . . .
H44B H 0.5059 0.2725 0.4289 0.082 Uiso 1 1 calc GR . . . .
H44C H 0.5224 0.4105 0.4514 0.082 Uiso 1 1 calc GR . . . .
C36A C 0.3269(6) 0.1844(12) 0.5223(6) 0.059(3) Uiso 0.83 1 d . . . A 1
H36A H 0.3179 0.1070 0.5309 0.071 Uiso 0.83 1 calc R . . A 1
C37 C 0.3547(6) 0.2556(11) 0.5872(7) 0.095(4) Uani 0.83 1 d . . . A 1
H37A H 0.3647 0.3339 0.5816 0.114 Uiso 0.83 1 calc R . . A 1
H37B H 0.3654 0.2303 0.6412 0.114 Uiso 0.83 1 calc R . . A 1
C36B C 0.340(3) 0.208(6) 0.532(2) 0.059(3) Uiso 0.17 1 d . . . A 2
H36B H 0.3746 0.2622 0.5695 0.071 Uiso 0.17 1 calc R . . A 2
C37B C 0.325(3) 0.137(5) 0.568(4) 0.099(19) Uiso 0.17 1 d . . . A 2
H37C H 0.2914 0.0815 0.5325 0.119 Uiso 0.17 1 calc R . . A 2
H37D H 0.3479 0.1396 0.6292 0.119 Uiso 0.17 1 calc R . . A 2
O1 O 0.5920(2) -0.4258(4) 0.3128(4) 0.0632(15) Uani 1 1 d . . . . .
H1 H 0.5707 -0.4887 0.2963 0.095 Uiso 1 1 calc GR . . . .
O2 O 0.2308(2) 0.1097(5) 0.1310(3) 0.0577(14) Uani 1 1 d . . . . .
H2 H 0.2236 0.0672 0.1589 0.087 Uiso 1 1 calc GR . . . .
O3 O 0.3324(2) 0.0753(4) 0.0625(3) 0.0389(11) Uani 1 1 d . . . . .
O4 O 0.4286(3) 0.2428(4) 0.1255(3) 0.0569(14) Uani 1 1 d . . . . .
O5 O 0.5070(3) 0.3634(5) 0.2327(4) 0.0691(16) Uani 1 1 d . . . . .
C1 C 0.4299(3) -0.1832(6) 0.3243(4) 0.0435(18) Uani 1 1 d . . . . .
H1A H 0.4135 -0.1417 0.3510 0.052 Uiso 1 1 calc R . . . .
H1B H 0.3943 -0.2313 0.2747 0.052 Uiso 1 1 calc R . . . .
C2 C 0.4852(4) -0.2675(7) 0.3938(5) 0.056(2) Uani 1 1 d . . . . .
H2A H 0.4686 -0.3270 0.4121 0.067 Uiso 1 1 calc R . . . .
H2B H 0.5190 -0.2210 0.4463 0.067 Uiso 1 1 calc R . . . .
C3 C 0.5146(3) -0.3322(7) 0.3563(5) 0.051(2) Uani 1 1 d . . . . .
H3A H 0.4821 -0.3866 0.3088 0.061 Uiso 1 1 calc R . . . .
H3B H 0.5514 -0.3810 0.4034 0.061 Uiso 1 1 calc R . . . .
C4 C 0.5380(3) -0.2462(6) 0.3190(5) 0.0439(18) Uani 1 1 d . . . . .
C5 C 0.4821(3) -0.1573(6) 0.2535(4) 0.0371(16) Uani 1 1 d . . . . .
H5 H 0.4468 -0.2101 0.2064 0.045 Uiso 1 1 calc R . . . .
C6 C 0.4954(3) -0.0731(6) 0.2028(5) 0.0455(19) Uani 1 1 d . . . . .
H6A H 0.5252 -0.0093 0.2426 0.055 Uiso 1 1 calc R . . . .
H6B H 0.5160 -0.1189 0.1835 0.055 Uiso 1 1 calc R . . . .
C7 C 0.4320(3) -0.0172(6) 0.1214(4) 0.0412(18) Uani 1 1 d . . . . .
H7A H 0.4419 0.0366 0.0915 0.049 Uiso 1 1 calc R . . . .
H7B H 0.4038 -0.0810 0.0795 0.049 Uiso 1 1 calc R . . . .
C8 C 0.3959(3) 0.0529(6) 0.1459(4) 0.0380(18) Uani 1 1 d . . . . .
C9 C 0.3878(3) -0.0284(6) 0.2037(4) 0.0346(16) Uani 1 1 d . . . . .
H9 H 0.3618 -0.0970 0.1644 0.042 Uiso 1 1 calc R . . . .
C10 C 0.4505(3) -0.0881(6) 0.2876(4) 0.0347(16) Uani 1 1 d . . . . .
C11 C 0.3428(3) 0.0352(6) 0.2164(4) 0.0416(18) Uani 1 1 d . . . . .
H11A H 0.3390 -0.0123 0.2553 0.050 Uiso 1 1 calc R . . . .
H11B H 0.3605 0.1140 0.2436 0.050 Uiso 1 1 calc R . . . .
C12 C 0.2768(3) 0.0492(6) 0.1256(4) 0.0409(18) Uani 1 1 d . . . . .
H12 H 0.2598 -0.0321 0.1013 0.049 Uiso 1 1 calc R . . . .
C13 C 0.2789(3) 0.1192(6) 0.0579(4) 0.0410(17) Uani 1 1 d . . . . .
C14 C 0.2197(4) 0.0859(7) -0.0366(5) 0.056(2) Uani 1 1 d . . . . .
H14 H 0.2283 0.0339 -0.0661 0.068 Uiso 1 1 calc R . . . .
C15 C 0.1619(5) 0.1165(11) -0.0809(6) 0.121(4) Uani 1 1 d . . . . .
H15A H 0.1492 0.1684 -0.0562 0.145 Uiso 1 1 calc R . . . .
H15B H 0.1309 0.0876 -0.1391 0.145 Uiso 1 1 calc R . . . .
C16 C 0.2828(4) 0.2545(6) 0.0735(5) 0.057(2) Uani 1 1 d . . . . .
H16A H 0.3167 0.2715 0.1360 0.085 Uiso 1 1 calc GR . . . .
H16B H 0.2416 0.2830 0.0558 0.085 Uiso 1 1 calc GR . . . .
H16C H 0.2924 0.2948 0.0387 0.085 Uiso 1 1 calc GR . . . .
C17 C 0.4323(3) 0.1719(6) 0.1910(4) 0.0432(18) Uani 1 1 d . . . . .
H17A H 0.4122 0.2149 0.2120 0.052 Uiso 1 1 calc R . . . .
H17B H 0.4776 0.1557 0.2419 0.052 Uiso 1 1 calc R . . . .
C18 C 0.5490(3) -0.3264(6) 0.2636(5) 0.053(2) Uani 1 1 d . . . . .
H18A H 0.5070 -0.3573 0.2118 0.064 Uiso 1 1 calc R . . . .
H18B H 0.5668 -0.2767 0.2419 0.064 Uiso 1 1 calc R . . . .
C19 C 0.6031(3) -0.1878(7) 0.3939(5) 0.060(2) Uani 1 1 d . . . . .
H19A H 0.6001 -0.1520 0.4367 0.090 Uiso 1 1 calc GR . . . .
H19B H 0.6135 -0.1264 0.3692 0.090 Uiso 1 1 calc GR . . . .
H19C H 0.6369 -0.2483 0.4230 0.090 Uiso 1 1 calc GR . . . .
C20 C 0.4963(3) 0.0038(6) 0.3629(4) 0.052(2) Uani 1 1 d . . . . .
H20A H 0.5236 -0.0375 0.4195 0.078 Uiso 1 1 calc GR . . . .
H20B H 0.4706 0.0639 0.3643 0.078 Uiso 1 1 calc GR . . . .
H20C H 0.5233 0.0423 0.3518 0.078 Uiso 1 1 calc GR . . . .
C21 C 0.4685(4) 0.3358(7) 0.1552(6) 0.0514(19) Uani 1 1 d . . . . .
C22 C 0.4596(4) 0.4026(7) 0.0810(5) 0.078(3) Uani 1 1 d . . . . .
H22A H 0.4213 0.4528 0.0511 0.116 Uiso 1 1 calc GR . . . .
H22B H 0.4544 0.3459 0.0391 0.116 Uiso 1 1 calc GR . . . .
H22C H 0.4972 0.4524 0.1050 0.116 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.0664(3) 0.1246(6) 0.0736(4) 0.1085(19) Uani 0.5 1 d . . . B 1
C45 C 0.0000 0.200(3) 0.0000 0.086(8) Uani 0.5 2 d S T P B 1
H45 H -0.0085 0.2518 0.0322 0.103 Uiso 0.5 1 d R . . B 1
Cl2 Cl 0.0000 0.348(2) 0.0000 0.109(8) Uani 0.25 2 d S T P C 2
Cl3 Cl 0.0635(7) 0.2072(15) 0.0145(11) 0.116(4) Uani 0.25 1 d . . . C 2
Cl4 Cl 0.0283(15) 0.301(3) -0.019(2) 0.107(11) Uani 0.125 1 d . . . C 2
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
C40 O6 H6 109.5 . .
C34 O7 H7 109.5 . .
C35 O8 C30 120.8(5) . .
C43 O9 C39 116.5(5) . .
H23A C23 H23B 107.8 . .
C24 C23 H23A 109.0 . .
C24 C23 H23B 109.0 . .
C24 C23 C32 113.0(5) . .
C32 C23 H23A 109.0 . .
C32 C23 H23B 109.0 . .
C23 C24 H24A 109.3 . .
C23 C24 H24B 109.3 . .
C23 C24 C25 111.5(6) . .
H24A C24 H24B 108.0 . .
C25 C24 H24A 109.3 . .
C25 C24 H24B 109.3 . .
C24 C25 H25A 108.8 . .
C24 C25 H25B 108.8 . .
C24 C25 C26 113.9(6) . .
H25A C25 H25B 107.7 . .
C26 C25 H25A 108.8 . .
C26 C25 H25B 108.8 . .
C25 C26 C27 107.9(5) . .
C40 C26 C25 106.9(6) . .
C40 C26 C27 107.6(5) . .
C40 C26 C41 108.2(5) . .
C41 C26 C25 111.0(6) . .
C41 C26 C27 114.8(5) . .
C26 C27 H27 104.5 . .
C26 C27 C32 116.3(5) . .
C28 C27 C26 115.2(5) . .
C28 C27 H27 104.5 . .
C28 C27 C32 110.4(5) . .
C32 C27 H27 104.5 . .
C27 C28 H28A 109.3 . .
C27 C28 H28B 109.3 . .
H28A C28 H28B 108.0 . .
C29 C28 C27 111.4(5) . .
C29 C28 H28A 109.3 . .
C29 C28 H28B 109.3 . .
C28 C29 H29A 109.0 . .
C28 C29 H29B 109.0 . .
C28 C29 C30 112.9(5) . .
H29A C29 H29B 107.8 . .
C30 C29 H29A 109.0 . .
C30 C29 H29B 109.0 . .
O8 C30 C29 104.8(5) . .
O8 C30 C31 109.0(5) . .
O8 C30 C39 112.1(5) . .
C29 C30 C31 108.7(5) . .
C29 C30 C39 109.2(5) . .
C31 C30 C39 112.8(5) . .
C30 C31 H31 104.6 . .
C30 C31 C32 116.6(5) . .
C30 C31 C33 108.4(5) . .
C32 C31 H31 104.6 . .
C33 C31 H31 104.6 . .
C33 C31 C32 116.6(5) . .
C23 C32 C31 108.1(5) . .
C27 C32 C23 106.6(5) . .
C27 C32 C31 106.4(5) . .
C42 C32 C23 108.0(5) . .
C42 C32 C27 115.1(5) . .
C42 C32 C31 112.2(5) . .
C31 C33 H33A 109.9 . .
C31 C33 H33B 109.9 . .
H33A C33 H33B 108.3 . .
C34 C33 C31 108.8(5) . .
C34 C33 H33A 109.9 . .
C34 C33 H33B 109.9 . .
O7 C34 C33 111.0(6) . .
O7 C34 H34 107.8 . .
O7 C34 C35 108.0(5) . .
C33 C34 H34 107.8 . .
C33 C34 C35 114.2(5) . .
C35 C34 H34 107.8 . .
O8 C35 C34 110.0(5) . .
O8 C35 C38 111.3(5) . .
O8 C35 C36A 107.1(7) . .
O8 C35 C36B 94(2) . .
C34 C35 C36B 117(3) . .
C38 C35 C34 112.8(6) . .
C38 C35 C36B 110(3) . .
C36A C35 C34 107.1(6) . .
C36A C35 C38 108.3(7) . .
C35 C38 H38A 109.5 . .
C35 C38 H38B 109.5 . .
C35 C38 H38C 109.5 . .
H38A C38 H38B 109.5 . .
H38A C38 H38C 109.5 . .
H38B C38 H38C 109.5 . .
O9 C39 C30 109.9(5) . .
O9 C39 H39A 109.7 . .
O9 C39 H39B 109.7 . .
C30 C39 H39A 109.7 . .
C30 C39 H39B 109.7 . .
H39A C39 H39B 108.2 . .
O6 C40 C26 111.5(6) . .
O6 C40 H40A 109.3 . .
O6 C40 H40B 109.3 . .
C26 C40 H40A 109.3 . .
C26 C40 H40B 109.3 . .
H40A C40 H40B 108.0 . .
C26 C41 H41A 109.5 . .
C26 C41 H41B 109.5 . .
C26 C41 H41C 109.5 . .
H41A C41 H41B 109.5 . .
H41A C41 H41C 109.5 . .
H41B C41 H41C 109.5 . .
C32 C42 H42A 109.5 . .
C32 C42 H42B 109.5 . .
C32 C42 H42C 109.5 . .
H42A C42 H42B 109.5 . .
H42A C42 H42C 109.5 . .
H42B C42 H42C 109.5 . .
O9 C43 C44 112.3(6) . .
O10 C43 O9 122.5(7) . .
O10 C43 C44 125.2(7) . .
C43 C44 H44A 109.5 . .
C43 C44 H44B 109.5 . .
C43 C44 H44C 109.5 . .
H44A C44 H44B 109.5 . .
H44A C44 H44C 109.5 . .
H44B C44 H44C 109.5 . .
C35 C36A H36A 117.1 . .
C37 C36A C35 125.9(11) . .
C37 C36A H36A 117.1 . .
C36A C37 H37A 120.0 . .
C36A C37 H37B 120.0 . .
H37A C37 H37B 120.0 . .
C35 C36B H36B 117.5 . .
C37B C36B C35 125(5) . .
C37B C36B H36B 117.5 . .
C36B C37B H37C 120.0 . .
C36B C37B H37D 120.0 . .
H37C C37B H37D 120.0 . .
C18 O1 H1 109.5 . .
C12 O2 H2 109.5 . .
C8 O3 C13 122.3(5) . .
C21 O4 C17 116.9(5) . .
H1A C1 H1B 107.7 . .
C2 C1 H1A 108.9 . .
C2 C1 H1B 108.9 . .
C2 C1 C10 113.5(5) . .
C10 C1 H1A 108.9 . .
C10 C1 H1B 108.9 . .
C1 C2 H2A 109.4 . .
C1 C2 H2B 109.4 . .
C1 C2 C3 111.2(5) . .
H2A C2 H2B 108.0 . .
C3 C2 H2A 109.4 . .
C3 C2 H2B 109.4 . .
C2 C3 H3A 108.8 . .
C2 C3 H3B 108.8 . .
C2 C3 C4 113.7(6) . .
H3A C3 H3B 107.7 . .
C4 C3 H3A 108.8 . .
C4 C3 H3B 108.8 . .
C3 C4 C5 108.5(5) . .
C3 C4 C18 105.7(6) . .
C5 C4 C18 107.4(5) . .
C19 C4 C3 111.5(6) . .
C19 C4 C5 115.4(6) . .
C19 C4 C18 107.8(5) . .
C4 C5 H5 103.6 . .
C4 C5 C10 117.3(5) . .
C6 C5 C4 114.9(5) . .
C6 C5 H5 103.6 . .
C6 C5 C10 111.6(5) . .
C10 C5 H5 103.6 . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 108.0 . .
C7 C6 C5 110.9(5) . .
C7 C6 H6A 109.5 . .
C7 C6 H6B 109.5 . .
C6 C7 H7A 109.1 . .
C6 C7 H7B 109.1 . .
H7A C7 H7B 107.8 . .
C8 C7 C6 112.6(5) . .
C8 C7 H7A 109.1 . .
C8 C7 H7B 109.1 . .
O3 C8 C7 105.1(5) . .
O3 C8 C9 108.2(5) . .
O3 C8 C17 111.0(5) . .
C7 C8 C9 109.0(5) . .
C7 C8 C17 108.9(5) . .
C17 C8 C9 114.4(5) . .
C8 C9 H9 104.0 . .
C8 C9 C10 117.2(5) . .
C10 C9 H9 104.0 . .
C11 C9 C8 108.7(5) . .
C11 C9 H9 104.0 . .
C11 C9 C10 117.1(5) . .
C1 C10 C5 107.3(5) . .
C1 C10 C9 108.3(5) . .
C1 C10 C20 108.2(5) . .
C5 C10 C9 105.8(5) . .
C20 C10 C5 114.3(5) . .
C20 C10 C9 112.7(5) . .
C9 C11 H11A 110.1 . .
C9 C11 H11B 110.1 . .
H11A C11 H11B 108.4 . .
C12 C11 C9 108.0(5) . .
C12 C11 H11A 110.1 . .
C12 C11 H11B 110.1 . .
O2 C12 C11 111.8(5) . .
O2 C12 H12 107.8 . .
O2 C12 C13 107.8(5) . .
C11 C12 H12 107.8 . .
C11 C12 C13 113.6(5) . .
C13 C12 H12 107.8 . .
O3 C13 C12 109.5(5) . .
O3 C13 C14 102.7(5) . .
O3 C13 C16 112.3(5) . .
C14 C13 C12 109.4(5) . .
C14 C13 C16 111.5(6) . .
C16 C13 C12 111.1(6) . .
C13 C14 H14 114.7 . .
C15 C14 C13 130.6(8) . .
C15 C14 H14 114.7 . .
C14 C15 H15A 120.0 . .
C14 C15 H15B 120.0 . .
H15A C15 H15B 120.0 . .
C13 C16 H16A 109.5 . .
C13 C16 H16B 109.5 . .
C13 C16 H16C 109.5 . .
H16A C16 H16B 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
O4 C17 C8 107.5(5) . .
O4 C17 H17A 110.2 . .
O4 C17 H17B 110.2 . .
C8 C17 H17A 110.2 . .
C8 C17 H17B 110.2 . .
H17A C17 H17B 108.5 . .
O1 C18 C4 113.6(6) . .
O1 C18 H18A 108.9 . .
O1 C18 H18B 108.9 . .
C4 C18 H18A 108.9 . .
C4 C18 H18B 108.9 . .
H18A C18 H18B 107.7 . .
C4 C19 H19A 109.5 . .
C4 C19 H19B 109.5 . .
C4 C19 H19C 109.5 . .
H19A C19 H19B 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C10 C20 H20A 109.5 . .
C10 C20 H20B 109.5 . .
C10 C20 H20C 109.5 . .
H20A C20 H20B 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
O4 C21 C22 111.8(7) . .
O5 C21 O4 123.9(7) . .
O5 C21 C22 124.3(7) . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22B 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
Cl1 C45 Cl1 118.5(18) . 2
Cl1 C45 H45 107.7 2 .
Cl1 C45 H45 107.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O6 H6 0.8200 .
O6 C40 1.436(8) .
O7 H7 0.8200 .
O7 C34 1.431(8) .
O8 C30 1.438(7) .
O8 C35 1.438(8) .
O9 C39 1.452(6) .
O9 C43 1.336(7) .
O10 C43 1.193(8) .
C23 H23A 0.9700 .
C23 H23B 0.9700 .
C23 C24 1.511(9) .
C23 C32 1.558(9) .
C24 H24A 0.9700 .
C24 H24B 0.9700 .
C24 C25 1.525(10) .
C25 H25A 0.9700 .
C25 H25B 0.9700 .
C25 C26 1.538(9) .
C26 C27 1.540(8) .
C26 C40 1.513(9) .
C26 C41 1.532(8) .
C27 H27 0.9800 .
C27 C28 1.536(8) .
C27 C32 1.556(8) .
C28 H28A 0.9700 .
C28 H28B 0.9700 .
C28 C29 1.517(8) .
C29 H29A 0.9700 .
C29 H29B 0.9700 .
C29 C30 1.521(9) .
C30 C31 1.521(8) .
C30 C39 1.525(8) .
C31 H31 0.9800 .
C31 C32 1.565(8) .
C31 C33 1.525(8) .
C32 C42 1.531(8) .
C33 H33A 0.9700 .
C33 H33B 0.9700 .
C33 C34 1.508(8) .
C34 H34 0.9800 .
C34 C35 1.528(9) .
C35 C38 1.508(9) .
C35 C36A 1.499(10) .
C35 C36B 1.53(3) .
C38 H38A 0.9600 .
C38 H38B 0.9600 .
C38 H38C 0.9600 .
C39 H39A 0.9700 .
C39 H39B 0.9700 .
C40 H40A 0.9700 .
C40 H40B 0.9700 .
C41 H41A 0.9600 .
C41 H41B 0.9600 .
C41 H41C 0.9600 .
C42 H42A 0.9600 .
C42 H42B 0.9600 .
C42 H42C 0.9600 .
C43 C44 1.482(9) .
C44 H44A 0.9600 .
C44 H44B 0.9600 .
C44 H44C 0.9600 .
C36A H36A 0.9300 .
C36A C37 1.249(14) .
C37 H37A 0.9300 .
C37 H37B 0.9300 .
C36B H36B 0.9300 .
C36B C37B 1.26(3) .
C37B H37C 0.9300 .
C37B H37D 0.9300 .
O1 H1 0.8200 .
O1 C18 1.425(8) .
O2 H2 0.8200 .
O2 C12 1.444(7) .
O3 C8 1.430(7) .
O3 C13 1.439(7) .
O4 C17 1.432(7) .
O4 C21 1.314(8) .
O5 C21 1.198(8) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C1 C2 1.523(9) .
C1 C10 1.541(8) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C2 C3 1.528(9) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C3 C4 1.534(9) .
C4 C5 1.543(9) .
C4 C18 1.545(9) .
C4 C19 1.520(9) .
C5 H5 0.9800 .
C5 C6 1.538(8) .
C5 C10 1.547(8) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C6 C7 1.523(9) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C7 C8 1.513(8) .
C8 C9 1.545(8) .
C8 C17 1.532(9) .
C9 H9 0.9800 .
C9 C10 1.550(8) .
C9 C11 1.523(8) .
C10 C20 1.542(8) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C11 C12 1.504(8) .
C12 H12 0.9800 .
C12 C13 1.544(8) .
C13 C14 1.514(9) .
C13 C16 1.515(9) .
C14 H14 0.9300 .
C14 C15 1.233(10) .
C15 H15A 0.9300 .
C15 H15B 0.9300 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 C22 1.486(9) .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
Cl1 C45 1.619(15) .
C45 Cl1 1.619(15) 2
C45 H45 0.9701 .
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
O7 C34 C35 O8 167.9(5)
O7 C34 C35 C38 42.9(7)
O7 C34 C35 C36A -76.1(8)
O7 C34 C35 C36B -87(3)
O8 C30 C31 C32 167.2(5)
O8 C30 C31 C33 -58.8(6)
O8 C30 C39 O9 -49.7(7)
O8 C35 C36A C37 7.0(16)
O8 C35 C36B C37B 163(6)
C23 C24 C25 C26 55.0(8)
C24 C23 C32 C27 54.6(7)
C24 C23 C32 C31 168.7(5)
C24 C23 C32 C42 -69.6(7)
C24 C25 C26 C27 -51.9(7)
C24 C25 C26 C40 -167.4(5)
C24 C25 C26 C41 74.8(7)
C25 C26 C27 C28 -174.5(5)
C25 C26 C27 C32 54.1(7)
C25 C26 C40 O6 -56.8(7)
C26 C27 C28 C29 166.1(5)
C26 C27 C32 C23 -55.3(6)
C26 C27 C32 C31 -170.5(5)
C26 C27 C32 C42 64.6(7)
C27 C26 C40 O6 -172.5(5)
C27 C28 C29 C30 57.8(7)
C28 C27 C32 C23 171.2(5)
C28 C27 C32 C31 55.9(6)
C28 C27 C32 C42 -69.0(6)
C28 C29 C30 O8 -168.8(5)
C28 C29 C30 C31 -52.4(7)
C28 C29 C30 C39 70.9(7)
C29 C30 C31 C32 53.6(7)
C29 C30 C31 C33 -172.5(5)
C29 C30 C39 O9 66.0(7)
C30 O8 C35 C34 -44.7(7)
C30 O8 C35 C38 81.1(7)
C30 O8 C35 C36A -160.7(7)
C30 O8 C35 C36B -166(3)
C30 C31 C32 C23 -169.9(5)
C30 C31 C32 C27 -55.7(7)
C30 C31 C32 C42 71.1(7)
C30 C31 C33 C34 61.2(6)
C31 C30 C39 O9 -173.1(5)
C31 C33 C34 O7 -177.0(5)
C31 C33 C34 C35 -54.7(7)
C32 C23 C24 C25 -56.5(8)
C32 C27 C28 C29 -59.7(6)
C32 C31 C33 C34 -164.9(5)
C33 C31 C32 C23 60.0(7)
C33 C31 C32 C27 174.2(5)
C33 C31 C32 C42 -59.1(7)
C33 C34 C35 O8 43.9(7)
C33 C34 C35 C38 -81.1(7)
C33 C34 C35 C36A 159.9(7)
C33 C34 C35 C36B 149(3)
C34 C35 C36A C37 -111.0(13)
C34 C35 C36B C37B 48(7)
C35 O8 C30 C29 169.6(5)
C35 O8 C30 C31 53.5(7)
C35 O8 C30 C39 -72.1(7)
C38 C35 C36A C37 127.1(13)
C38 C35 C36B C37B -83(6)
C39 O9 C43 O10 -1.7(10)
C39 O9 C43 C44 -179.4(5)
C39 C30 C31 C32 -67.6(7)
C39 C30 C31 C33 66.3(7)
C40 C26 C27 C28 -59.4(7)
C40 C26 C27 C32 169.2(5)
C41 C26 C27 C28 61.1(7)
C41 C26 C27 C32 -70.3(7)
C41 C26 C40 O6 62.9(7)
C43 O9 C39 C30 -122.2(6)
C36A C35 C36B C37B 2(8)
C36B C35 C36A C37 27(12)
O2 C12 C13 O3 169.7(5)
O2 C12 C13 C14 -78.5(7)
O2 C12 C13 C16 45.1(7)
O3 C8 C9 C10 166.6(5)
O3 C8 C9 C11 -57.9(6)
O3 C8 C17 O4 -50.2(7)
O3 C13 C14 C15 -168.5(10)
C1 C2 C3 C4 55.0(8)
C2 C1 C10 C5 53.5(7)
C2 C1 C10 C9 167.3(5)
C2 C1 C10 C20 -70.2(7)
C2 C3 C4 C5 -50.9(7)
C2 C3 C4 C18 -165.8(6)
C2 C3 C4 C19 77.3(7)
C3 C4 C5 C6 -173.9(6)
C3 C4 C5 C10 51.9(7)
C3 C4 C18 O1 -54.7(7)
C4 C5 C6 C7 162.9(5)
C4 C5 C10 C1 -52.9(7)
C4 C5 C10 C9 -168.3(5)
C4 C5 C10 C20 67.1(7)
C5 C4 C18 O1 -170.4(5)
C5 C6 C7 C8 57.6(7)
C6 C5 C10 C1 171.6(5)
C6 C5 C10 C9 56.1(6)
C6 C5 C10 C20 -68.5(7)
C6 C7 C8 O3 -167.5(5)
C6 C7 C8 C9 -51.7(7)
C6 C7 C8 C17 73.6(7)
C7 C8 C9 C10 52.9(7)
C7 C8 C9 C11 -171.6(5)
C7 C8 C17 O4 64.9(7)
C8 O3 C13 C12 -44.2(7)
C8 O3 C13 C14 -160.4(5)
C8 O3 C13 C16 79.7(7)
C8 C9 C10 C1 -169.2(5)
C8 C9 C10 C5 -54.4(7)
C8 C9 C10 C20 71.2(7)
C8 C9 C11 C12 62.9(7)
C9 C8 C17 O4 -172.9(5)
C9 C11 C12 O2 -179.6(5)
C9 C11 C12 C13 -57.3(7)
C10 C1 C2 C3 -56.6(8)
C10 C5 C6 C7 -60.4(7)
C10 C9 C11 C12 -161.5(5)
C11 C9 C10 C1 58.9(7)
C11 C9 C10 C5 173.7(5)
C11 C9 C10 C20 -60.7(7)
C11 C12 C13 O3 45.2(7)
C11 C12 C13 C14 157.0(6)
C11 C12 C13 C16 -79.4(7)
C12 C13 C14 C15 75.3(12)
C13 O3 C8 C7 167.7(5)
C13 O3 C8 C9 51.4(7)
C13 O3 C8 C17 -74.8(6)
C16 C13 C14 C15 -48.1(12)
C17 O4 C21 O5 0.1(11)
C17 O4 C21 C22 -179.5(6)
C17 C8 C9 C10 -69.2(7)
C17 C8 C9 C11 66.4(7)
C18 C4 C5 C6 -60.1(7)
C18 C4 C5 C10 165.8(5)
C19 C4 C5 C6 60.2(8)
C19 C4 C5 C10 -74.0(7)
C19 C4 C18 O1 64.7(7)
C21 O4 C17 C8 -165.4(6)
