# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mvt_zasiceni_1563

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_database_code_depnum_ccdc_archive 'CCDC 1411164'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-11-13 downloaded from the CCDC.
;

_audit_creation_date             2013-10-30T11:24:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_chemical_name_systematic        
;
8-cyclopentyl-10-methyl-6,7-dioxaspiro[4.5]decane-8,10-diol
;
_chemical_formula_moiety         'C14 H24 O4'
_chemical_formula_sum            'C14 H24 O4'
_chemical_formula_weight         256.33
_chemical_melting_point          384(1)
_chemical_compound_source        synthetic

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.0638(4)
_cell_length_b                   10.8218(4)
_cell_length_c                   11.7331(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.810(3)
_cell_angle_gamma                90
_cell_volume                     1379.89(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5463
_cell_measurement_theta_min      3.89
_cell_measurement_theta_max      30.293

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.94
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_F_000             560
_exptl_special_details           
; Recrystallized from petrol-ether
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm using CrysAlisPro 
 (Agilent Technologies,2013).
;
_exptl_absorpt_correction_T_min  0.9042
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.921
_shelx_estimated_absorpt_T_max   0.992

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) (Agilent Technologies)'
_diffrn_source_current           40
_diffrn_source_voltage           40
_diffrn_source_power             1.6
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Sapphire3 (Agilent Technologies)'
_diffrn_detector_area_resol_mean 16.328
_diffrn_measurement_specimen_support 'glass fiber'
_diffrn_radiation_collimation    '0.8 mm'
_diffrn_orient_matrix_ub_11      0.0613493
_diffrn_orient_matrix_ub_12      0.0166207
_diffrn_orient_matrix_ub_13      -0.0029594
_diffrn_orient_matrix_ub_21      -0.0216199
_diffrn_orient_matrix_ub_22      0.0340206
_diffrn_orient_matrix_ub_23      -0.0514745
_diffrn_orient_matrix_ub_31      -0.0053673
_diffrn_orient_matrix_ub_32      0.0535273
_diffrn_orient_matrix_ub_33      0.0336048
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Gemini S (Agilent Technologies)'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_number            18416
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.38
_diffrn_reflns_theta_max         30.515
_diffrn_reflns_theta_full        27
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.93
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.93
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.93
_reflns_number_total             3924
_reflns_number_gt                3108
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2013)'
_computing_structure_solution    
; SUPERFLIP (Palatinus L. and Chapuis G., 2007) and 
  EDMA (Van Smaalen et al, 2003)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   iterative
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0692P)²+0.2002P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3924
_refine_ls_number_parameters     210
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.136
_refine_ls_wR_factor_gt          0.1257
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1' C 0.09360(11) 0.89631(11) 0.85784(10) 0.0418(3) Uani 1 d . .
H1' H 0.0698 0.9818 0.8704 0.05 Uiso 1 calc . .
C1 C -0.39309(12) 0.79569(14) 0.62322(12) 0.0534(3) Uani 1 d . .
H1A H -0.4049 0.7855 0.5397 0.064 Uiso 0.669(12) calc A 1
H1B H -0.3939 0.7147 0.6585 0.064 Uiso 0.669(12) calc A 1
H1C H -0.4184 0.8068 0.5401 0.064 Uiso 0.331(12) calc A 2
H1D H -0.3878 0.708 0.6407 0.064 Uiso 0.331(12) calc A 2
C2' C 0.13302(13) 0.83524(15) 0.97726(11) 0.0567(3) Uani 1 d . .
H2'A H 0.1088 0.8865 1.037 0.068 Uiso 0.538(9) calc B 1
H2'B H 0.0937 0.7552 0.9782 0.068 Uiso 0.538(9) calc B 1
H2'C H 0.083 0.8631 1.0319 0.068 Uiso 0.462(9) calc B 2
H2'D H 0.1296 0.7458 0.9719 0.068 Uiso 0.462(9) calc B 2
C2A C -0.4938(6) 0.8753(8) 0.6546(8) 0.101(2) Uani 0.669(12) d A 1
H2AA H -0.5489 0.8263 0.6916 0.121 Uiso 0.669(12) calc A 1
H2AB H -0.5412 0.9139 0.5858 0.121 Uiso 0.669(12) calc A 1
C3A C -0.4289(3) 0.9727(5) 0.7379(4) 0.0721(12) Uani 0.669(12) d A 1
H3AA H -0.4155 0.9434 0.8174 0.087 Uiso 0.669(12) calc A 1
H3AB H -0.4763 1.0487 0.7322 0.087 Uiso 0.669(12) calc A 1
C2B C -0.4814(10) 0.8606(11) 0.6893(12) 0.073(3) Uani 0.331(12) d A 2
H2BA H -0.4728 0.8296 0.768 0.088 Uiso 0.331(12) calc A 2
H2BB H -0.5662 0.8513 0.65 0.088 Uiso 0.331(12) calc A 2
C3B C -0.4383(8) 0.9974(11) 0.6878(15) 0.103(4) Uani 0.331(12) d A 2
H3BA H -0.4764 1.0376 0.6161 0.123 Uiso 0.331(12) calc A 2
H3BB H -0.4597 1.0428 0.7525 0.123 Uiso 0.331(12) calc A 2
C4'A C 0.3094(5) 0.9168(5) 0.9191(5) 0.0618(12) Uani 0.538(9) d B 1
H4'A H 0.3916 0.9001 0.9053 0.074 Uiso 0.538(9) calc B 1
H4'B H 0.3068 0.9995 0.9503 0.074 Uiso 0.538(9) calc B 1
C3'A C 0.2696(3) 0.8204(5) 0.9994(3) 0.0578(9) Uani 0.538(9) d B 1
H3'A H 0.2928 0.7378 0.9797 0.069 Uiso 0.538(9) calc B 1
H3'B H 0.3052 0.8372 1.0799 0.069 Uiso 0.538(9) calc B 1
C4'B C 0.3209(6) 0.8695(9) 0.9018(5) 0.0670(16) Uani 0.462(9) d B 2
H4'C H 0.3876 0.9279 0.9024 0.08 Uiso 0.462(9) calc B 2
H4'D H 0.3509 0.7864 0.8934 0.08 Uiso 0.462(9) calc B 2
C3'B C 0.2649(4) 0.8816(7) 1.0100(3) 0.0567(12) Uani 0.462(9) d B 2
H3'C H 0.2661 0.9671 1.0349 0.068 Uiso 0.462(9) calc B 2
H3'D H 0.3106 0.8324 1.0727 0.068 Uiso 0.462(9) calc B 2
C4 C -0.30600(12) 0.99235(12) 0.69708(12) 0.0509(3) Uani 1 d . .
H4A H -0.3164 1.045 0.629 0.061 Uiso 0.669(12) calc A 1
H4B H -0.2448 1.0285 0.758 0.061 Uiso 0.669(12) calc A 1
H4C H -0.2656 1.0144 0.7751 0.061 Uiso 0.331(12) calc A 2
H4D H -0.2803 1.0504 0.6433 0.061 Uiso 0.331(12) calc A 2
C5 C -0.27031(10) 0.86099(10) 0.66873(9) 0.0368(2) Uani 1 d . .
C5' C 0.21140(13) 0.89973(18) 0.80691(12) 0.0669(4) Uani 1 d . .
H5'A H 0.2113 0.9685 0.7539 0.08 Uiso 0.538(9) calc B 1
H5'B H 0.2235 0.8232 0.7674 0.08 Uiso 0.538(9) calc B 1
H5'C H 0.2058 0.84 0.7445 0.08 Uiso 0.462(9) calc B 2
H5'D H 0.2217 0.9811 0.7755 0.08 Uiso 0.462(9) calc B 2
C8 C -0.01422(10) 0.83398(9) 0.77948(8) 0.0341(2) Uani 1 d . .
H8 H -0.0397(17) 0.6812(18) 0.7124(17) 0.078(6) Uiso 1 d . .
O8 O 0.00884(9) 0.70811(8) 0.77131(8) 0.0487(2) Uani 1 d . .
O7 O -0.11546(7) 0.85383(8) 0.84015(6) 0.0407(2) Uani 1 d . .
O6 O -0.22510(8) 0.79253(8) 0.77439(6) 0.0430(2) Uani 1 d . .
C11 C -0.20518(13) 0.91958(12) 0.47751(9) 0.0467(3) Uani 1 d . .
H11A H -0.1444 0.9029 0.4309 0.07 Uiso 1 calc . .
H11B H -0.2071 1.0067 0.4927 0.07 Uiso 1 calc . .
H11C H -0.2845 0.8933 0.4369 0.07 Uiso 1 calc . .
C10 C -0.17266(10) 0.84970(9) 0.59180(8) 0.0340(2) Uani 1 d . .
C9 C -0.04932(10) 0.89479(9) 0.66034(8) 0.0338(2) Uani 1 d . .
H9A H 0.0145 0.8779 0.6159 0.041 Uiso 1 calc . .
H9B H -0.0532 0.9836 0.6704 0.041 Uiso 1 calc . .
H9 H -0.1508(17) 0.7075(17) 0.5039(17) 0.072(5) Uiso 1 d . .
O9 O -0.16364(9) 0.71917(7) 0.56900(7) 0.0439(2) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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' C8 1.5205(15) . ?
C1' C5' 1.5327(19) . ?
C1' C2' 1.5365(16) . ?
C1' H1' 0.98 . ?
C1 C2A 1.508(6) . ?
C1 C2B 1.528(9) . ?
C1 C5 1.5355(16) . ?
C1 H1A 0.97 . ?
C1 H1B 0.97 . ?
C1 H1C 0.97 . ?
C1 H1D 0.97 . ?
C2' C3'A 1.493(4) . ?
C2' C3'B 1.522(4) . ?
C2' H2'A 0.97 . ?
C2' H2'B 0.97 . ?
C2' H2'C 0.97 . ?
C2' H2'D 0.97 . ?
C2A C3A 1.523(7) . ?
C2A H2AA 0.97 . ?
C2A H2AB 0.97 . ?
C3A C4 1.539(4) . ?
C3A H3AA 0.97 . ?
C3A H3AB 0.97 . ?
C2B C3B 1.556(12) . ?
C2B H2BA 0.97 . ?
C2B H2BB 0.97 . ?
C3B C4 1.448(9) . ?
C3B H3BA 0.97 . ?
C3B H3BB 0.97 . ?
C4'A C3'A 1.525(7) . ?
C4'A C5' 1.551(6) . ?
C4'A H4'A 0.97 . ?
C4'A H4'B 0.97 . ?
C3'A H3'A 0.97 . ?
C3'A H3'B 0.97 . ?
C4'B C5' 1.520(6) . ?
C4'B C3'B 1.520(7) . ?
C4'B H4'C 0.97 . ?
C4'B H4'D 0.97 . ?
C3'B H3'C 0.97 . ?
C3'B H3'D 0.97 . ?
C4 C5 1.5286(16) . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C4 H4C 0.97 . ?
C4 H4D 0.97 . ?
C5 O6 1.4503(13) . ?
C5 C10 1.5371(14) . ?
C5' H5'A 0.97 . ?
C5' H5'B 0.97 . ?
C5' H5'C 0.97 . ?
C5' H5'D 0.97 . ?
C8 O8 1.3924(13) . ?
C8 O7 1.4515(12) . ?
C8 C9 1.5278(13) . ?
O8 H8 0.844(19) . ?
O7 O6 1.4682(11) . ?
C11 C10 1.5227(14) . ?
C11 H11A 0.96 . ?
C11 H11B 0.96 . ?
C11 H11C 0.96 . ?
C10 O9 1.4446(13) . ?
C10 C9 1.5281(15) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
O9 H9 0.81(2) . ?

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
C8 C1' C5' 113.77(10) . . ?
C8 C1' C2' 114.64(10) . . ?
C5' C1' C2' 104.43(10) . . ?
C8 C1' H1' 107.9 . . ?
C5' C1' H1' 107.9 . . ?
C2' C1' H1' 107.9 . . ?
C2A C1 C5 107.4(3) . . ?
C2B C1 C5 102.7(5) . . ?
C2A C1 H1A 110.2 . . ?
C5 C1 H1A 110.2 . . ?
C2A C1 H1B 110.2 . . ?
C5 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
C2B C1 H1C 111.2 . . ?
C5 C1 H1C 111.2 . . ?
C2B C1 H1D 111.2 . . ?
C5 C1 H1D 111.2 . . ?
H1C C1 H1D 109.1 . . ?
C3'A C2' C1' 108.05(17) . . ?
C3'B C2' C1' 100.6(2) . . ?
C3'A C2' H2'A 110.1 . . ?
C1' C2' H2'A 110.1 . . ?
C3'A C2' H2'B 110.1 . . ?
C1' C2' H2'B 110.1 . . ?
H2'A C2' H2'B 108.4 . . ?
C3'B C2' H2'C 111.7 . . ?
C1' C2' H2'C 111.7 . . ?
C3'B C2' H2'D 111.7 . . ?
C1' C2' H2'D 111.7 . . ?
H2'C C2' H2'D 109.4 . . ?
C1 C2A C3A 105.7(5) . . ?
C1 C2A H2AA 110.6 . . ?
C3A C2A H2AA 110.6 . . ?
C1 C2A H2AB 110.6 . . ?
C3A C2A H2AB 110.6 . . ?
H2AA C2A H2AB 108.7 . . ?
C2A C3A C4 103.5(4) . . ?
C2A C3A H3AA 111.1 . . ?
C4 C3A H3AA 111.1 . . ?
C2A C3A H3AB 111.1 . . ?
C4 C3A H3AB 111.1 . . ?
H3AA C3A H3AB 109 . . ?
C1 C2B C3B 101.8(7) . . ?
C1 C2B H2BA 111.4 . . ?
C3B C2B H2BA 111.4 . . ?
C1 C2B H2BB 111.4 . . ?
C3B C2B H2BB 111.4 . . ?
H2BA C2B H2BB 109.3 . . ?
C4 C3B C2B 105.7(8) . . ?
C4 C3B H3BA 110.6 . . ?
C2B C3B H3BA 110.6 . . ?
C4 C3B H3BB 110.6 . . ?
C2B C3B H3BB 110.6 . . ?
H3BA C3B H3BB 108.7 . . ?
C3'A C4'A C5' 101.9(4) . . ?
C3'A C4'A H4'A 111.4 . . ?
C5' C4'A H4'A 111.4 . . ?
C3'A C4'A H4'B 111.4 . . ?
C5' C4'A H4'B 111.4 . . ?
H4'A C4'A H4'B 109.3 . . ?
C2' C3'A C4'A 102.7(3) . . ?
C2' C3'A H3'A 111.2 . . ?
C4'A C3'A H3'A 111.2 . . ?
C2' C3'A H3'B 111.2 . . ?
C4'A C3'A H3'B 111.2 . . ?
H3'A C3'A H3'B 109.1 . . ?
C5' C4'B C3'B 101.5(4) . . ?
C5' C4'B H4'C 111.5 . . ?
C3'B C4'B H4'C 111.5 . . ?
C5' C4'B H4'D 111.5 . . ?
C3'B C4'B H4'D 111.5 . . ?
H4'C C4'B H4'D 109.3 . . ?
C4'B C3'B C2' 106.4(4) . . ?
C4'B C3'B H3'C 110.4 . . ?
C2' C3'B H3'C 110.4 . . ?
C4'B C3'B H3'D 110.4 . . ?
C2' C3'B H3'D 110.4 . . ?
H3'C C3'B H3'D 108.6 . . ?
C3B C4 C5 108.5(5) . . ?
C5 C4 C3A 102.7(2) . . ?
C5 C4 H4A 111.2 . . ?
C3A C4 H4A 111.2 . . ?
C5 C4 H4B 111.2 . . ?
C3A C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
C3B C4 H4C 110 . . ?
C5 C4 H4C 110 . . ?
C3B C4 H4D 110 . . ?
C5 C4 H4D 110 . . ?
H4C C4 H4D 108.4 . . ?
O6 C5 C4 110.53(9) . . ?
O6 C5 C1 101.71(9) . . ?
C4 C5 C1 104.82(10) . . ?
O6 C5 C10 107.08(9) . . ?
C4 C5 C10 116.14(9) . . ?
C1 C5 C10 115.63(9) . . ?
C4'B C5' C1' 109.2(3) . . ?
C1' C5' C4'A 100.5(2) . . ?
C1' C5' H5'A 111.7 . . ?
C4'A C5' H5'A 111.7 . . ?
C1' C5' H5'B 111.7 . . ?
C4'A C5' H5'B 111.7 . . ?
H5'A C5' H5'B 109.4 . . ?
C4'B C5' H5'C 109.8 . . ?
C1' C5' H5'C 109.8 . . ?
C4'B C5' H5'D 109.8 . . ?
C1' C5' H5'D 109.8 . . ?
H5'C C5' H5'D 108.3 . . ?
O8 C8 O7 110.28(8) . . ?
O8 C8 C1' 110.03(9) . . ?
O7 C8 C1' 103.17(8) . . ?
O8 C8 C9 112.14(9) . . ?
O7 C8 C9 107.33(8) . . ?
C1' C8 C9 113.46(9) . . ?
C8 O8 H8 107.3(13) . . ?
C8 O7 O6 108.24(7) . . ?
C5 O6 O7 109.69(7) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O9 C10 C11 109.62(8) . . ?
O9 C10 C9 108.89(9) . . ?
C11 C10 C9 110.18(9) . . ?
O9 C10 C5 105.49(8) . . ?
C11 C10 C5 113.68(9) . . ?
C9 C10 C5 108.79(8) . . ?
C8 C9 C10 113.12(8) . . ?
C8 C9 H9A 109 . . ?
C10 C9 H9A 109 . . ?
C8 C9 H9B 109 . . ?
C10 C9 H9B 109 . . ?
H9A C9 H9B 107.8 . . ?
C10 O9 H9 110.9(13) . . ?

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
_geom_torsion_publ_flag
C8 C1' C2' C3'A 132.3(3) . . . . ?
C5' C1' C2' C3'A 7.2(3) . . . . ?
C8 C1' C2' C3'B 158.0(3) . . . . ?
C5' C1' C2' C3'B 32.8(3) . . . . ?
C2B C1 C2A C3A 65(2) . . . . ?
C5 C1 C2A C3A -10.8(8) . . . . ?
C1 C2A C3A C4 31.6(8) . . . . ?
C2A C1 C2B C3B -68(2) . . . . ?
C5 C1 C2B C3B 39.9(11) . . . . ?
C1 C2B C3B C4 -35.4(15) . . . . ?
C3'B C2' C3'A C4'A -54.8(5) . . . . ?
C1' C2' C3'A C4'A 22.0(5) . . . . ?
C5' C4'A C3'A C2' -42.5(6) . . . . ?
C5' C4'B C3'B C2' 35.5(8) . . . . ?
C3'A C2' C3'B C4'B 66.4(7) . . . . ?
C1' C2' C3'B C4'B -43.3(6) . . . . ?
C2B C3B C4 C5 16.4(13) . . . . ?
C2B C3B C4 C3A -63.2(14) . . . . ?
C2A C3A C4 C3B 66.9(14) . . . . ?
C2A C3A C4 C5 -40.2(6) . . . . ?
C3B C4 C5 O6 -100.0(7) . . . . ?
C3A C4 C5 O6 -75.4(2) . . . . ?
C3B C4 C5 C1 8.9(7) . . . . ?
C3A C4 C5 C1 33.4(2) . . . . ?
C3B C4 C5 C10 137.8(7) . . . . ?
C3A C4 C5 C10 162.4(2) . . . . ?
C2A C1 C5 O6 100.8(4) . . . . ?
C2B C1 C5 O6 84.4(6) . . . . ?
C2A C1 C5 C4 -14.4(4) . . . . ?
C2B C1 C5 C4 -30.7(6) . . . . ?
C2A C1 C5 C10 -143.6(4) . . . . ?
C2B C1 C5 C10 -160.0(6) . . . . ?
C3'B C4'B C5' C1' -13.7(8) . . . . ?
C3'B C4'B C5' C4'A 55.4(10) . . . . ?
C8 C1' C5' C4'B -138.0(4) . . . . ?
C2' C1' C5' C4'B -12.3(4) . . . . ?
C8 C1' C5' C4'A -158.4(2) . . . . ?
C2' C1' C5' C4'A -32.7(3) . . . . ?
C3'A C4'A C5' C4'B -69.6(12) . . . . ?
C3'A C4'A C5' C1' 46.6(5) . . . . ?
C5' C1' C8 O8 68.05(13) . . . . ?
C2' C1' C8 O8 -52.06(13) . . . . ?
C5' C1' C8 O7 -174.28(10) . . . . ?
C2' C1' C8 O7 65.61(12) . . . . ?
C5' C1' C8 C9 -58.49(14) . . . . ?
C2' C1' C8 C9 -178.60(10) . . . . ?
O8 C8 O7 O6 -60.21(10) . . . . ?
C1' C8 O7 O6 -177.69(7) . . . . ?
C9 C8 O7 O6 62.21(9) . . . . ?
C4 C5 O6 O7 -60.74(11) . . . . ?
C1 C5 O6 O7 -171.63(8) . . . . ?
C10 C5 O6 O7 66.64(10) . . . . ?
C8 O7 O6 C5 -72.09(10) . . . . ?
O6 C5 C10 O9 61.16(10) . . . . ?
C4 C5 C10 O9 -174.82(9) . . . . ?
C1 C5 C10 O9 -51.35(12) . . . . ?
O6 C5 C10 C11 -178.71(9) . . . . ?
C4 C5 C10 C11 -54.69(13) . . . . ?
C1 C5 C10 C11 68.78(13) . . . . ?
O6 C5 C10 C9 -55.54(10) . . . . ?
C4 C5 C10 C9 68.48(12) . . . . ?
C1 C5 C10 C9 -168.05(10) . . . . ?
O8 C8 C9 C10 66.51(12) . . . . ?
O7 C8 C9 C10 -54.75(11) . . . . ?
C1' C8 C9 C10 -168.06(9) . . . . ?
O9 C10 C9 C8 -63.12(11) . . . . ?
C11 C10 C9 C8 176.62(9) . . . . ?
C5 C10 C9 C8 51.38(11) . . . . ?

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
O8 H8 O9 0.844(19) 2.004(19) 2.7552(13) 148.0(18) .
O9 H9 O7 0.81(2) 2.14(2) 2.9419(11) 170.8(17) 4_575
#----------------------------------------------------------------------------#
#                        END OF CIF                                          #
#----------------------------------------------------------------------------#
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_new

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_database_code_depnum_ccdc_archive 'CCDC 1411165'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-11-13 downloaded from the CCDC.
;

_audit_creation_date             2013-10-30T12:53:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_chemical_name_systematic        
;
8-isobutyl-10-methyl-6,7-dioxaspiro[4.5]decane-8,10-diol
;
_chemical_formula_moiety         'C13 H24 O4'
_chemical_formula_structural     'C13 H24 O4'
_chemical_formula_sum            'C13 H24 O4'
_chemical_formula_weight         244.32
_chemical_melting_point          337(1)
_chemical_compound_source        synthetic
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.8267(3)
_cell_length_b                   11.0347(5)
_cell_length_c                   21.6517(14)
_cell_angle_alpha                90
_cell_angle_beta                 97.322(5)
_cell_angle_gamma                90
_cell_volume                     1380.76(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6457
_cell_measurement_theta_min      3.529
_cell_measurement_theta_max      28.938

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_F_000             536
_exptl_special_details           
; Recrystallized from petrol-ether
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm using CrysAlisPro 
 (Agilent Technologies,2013).
;
_exptl_absorpt_correction_T_min  0.79183
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) (Agilent Technologies)'
_diffrn_source_current           50
_diffrn_source_voltage           40
_diffrn_source_power             2
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Sapphire3 (Agilent Technologies)'
_diffrn_detector_area_resol_mean 16.328
_diffrn_measurement_specimen_support 'glass fiber'
_diffrn_radiation_collimation    '0.8 mm'
_diffrn_orient_matrix_ub_11      -0.0128104
_diffrn_orient_matrix_ub_12      0.0321675
_diffrn_orient_matrix_ub_13      -0.0141818
_diffrn_orient_matrix_ub_21      0.1167072
_diffrn_orient_matrix_ub_22      0.018114
_diffrn_orient_matrix_ub_23      0.0008734
_diffrn_orient_matrix_ub_31      0.0323108
_diffrn_orient_matrix_ub_32      -0.0526216
_diffrn_orient_matrix_ub_33      -0.0083959
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Gemini S (Agilent Technologies)'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.05
_diffrn_reflns_number            17130
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.392
_diffrn_reflns_theta_max         29.623
_diffrn_reflns_theta_full        26.32
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.903
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.865
_reflns_number_total             6726
_reflns_number_gt                5378
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2013)'
_computing_structure_solution    
; SUPERFLIP (Palatinus L. and Chapuis G., 2007) and 
  EDMA (Van Smaalen et al, 2003)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   iterative
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0584P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6726
_refine_ls_number_parameters     358
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1229
_refine_ls_wR_factor_gt          0.1111
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.028

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0560(3) 0.36693(14) 0.52676(8) 0.0496(4) Uani 1 d . .
C1 C 0.2139(4) 0.2948(2) 0.56886(11) 0.0444(5) Uani 1 d . .
O2 O 0.1386(3) 0.37023(14) 0.46547(8) 0.0531(4) Uani 1 d . .
C2 C 0.1256(5) 0.3168(2) 0.63151(12) 0.0561(6) Uani 1 d . .
H2A H -0.0221 0.3586 0.6256 0.067 Uiso 0.428(16) calc A 1
H2B H 0.1067 0.2407 0.6527 0.067 Uiso 0.428(16) calc A 1
H2C H -0.04 0.3312 0.6258 0.067 Uiso 0.572(16) calc A 2
H2D H 0.1585 0.2477 0.6589 0.067 Uiso 0.572(16) calc A 2
O3 O -0.0437(3) 0.12915(17) 0.54949(10) 0.0537(5) Uani 1 d . .
H3 H -0.054(6) 0.062(4) 0.5427(15) 0.080(12) Uiso 1 d . .
C3A C 0.308(4) 0.3946(17) 0.6689(8) 0.084(6) Uani 0.428(16) d A 1
H3AA H 0.2373 0.4571 0.6916 0.101 Uiso 0.428(16) calc A 1
H3AB H 0.4083 0.3456 0.6983 0.101 Uiso 0.428(16) calc A 1
C3B C 0.256(2) 0.4290(9) 0.6585(6) 0.068(3) Uani 0.572(16) d A 2
H3BA H 0.2571 0.4336 0.7033 0.082 Uiso 0.572(16) calc A 2
H3BB H 0.1893 0.5028 0.6395 0.082 Uiso 0.572(16) calc A 2
C4A C 0.444(2) 0.4503(9) 0.6206(6) 0.068(3) Uani 0.428(16) d A 1
H4AA H 0.3639 0.5197 0.6006 0.081 Uiso 0.428(16) calc A 1
H4AB H 0.5973 0.4752 0.6392 0.081 Uiso 0.428(16) calc A 1
C4B C 0.5005(15) 0.4055(13) 0.6408(5) 0.080(3) Uani 0.572(16) d A 2
H4BA H 0.5869 0.4806 0.6404 0.096 Uiso 0.572(16) calc A 2
H4BB H 0.5856 0.3499 0.6699 0.096 Uiso 0.572(16) calc A 2
O4 O -0.1420(3) 0.22756(19) 0.43039(10) 0.0616(5) Uani 1 d . .
H4 H -0.177(6) 0.198(4) 0.4641(16) 0.084(12) Uiso 1 d . .
C5 C 0.4580(5) 0.3501(3) 0.57564(14) 0.0601(7) Uani 1 d . .
H5A H 0.5737 0.291 0.5917 0.072 Uiso 0.428(16) calc A 1
H5B H 0.495 0.3804 0.536 0.072 Uiso 0.428(16) calc A 1
H5C H 0.5722 0.288 0.5709 0.072 Uiso 0.572(16) calc A 2
H5D H 0.4678 0.4119 0.5442 0.072 Uiso 0.572(16) calc A 2
O5 O 0.0611(3) 0.02150(14) 0.04253(8) 0.0525(4) Uani 1 d . .
O6 O 0.1590(3) 0.00515(14) -0.01586(8) 0.0564(5) Uani 1 d . .
C6 C 0.1950(4) 0.16333(19) 0.54529(11) 0.0437(5) Uani 1 d . .
C7 C 0.3580(5) 0.0760(3) 0.58387(14) 0.0644(7) Uani 1 d . .
H7A H 0.324 -0.0055 0.5702 0.097 Uiso 1 calc . .
H7B H 0.3374 0.0833 0.627 0.097 Uiso 1 calc . .
H7C H 0.5151 0.0952 0.5787 0.097 Uiso 1 calc . .
H7 H -0.076(5) 0.328(3) 0.0390(14) 0.069(10) Uiso 1 d . .
O7 O -0.0583(3) 0.26023(16) 0.04548(9) 0.0519(5) Uani 1 d . .
O8 O -0.1207(4) 0.13671(18) -0.06563(11) 0.0619(5) Uani 1 d . .
H8 H -0.166(9) 0.168(5) -0.035(2) 0.14(2) Uiso 1 d . .
C8 C 0.2360(4) 0.1602(2) 0.47760(11) 0.0474(6) Uani 1 d . .
H8A H 0.1993 0.0797 0.4612 0.057 Uiso 1 calc . .
H8B H 0.3989 0.1746 0.4753 0.057 Uiso 1 calc . .
C24 C 0.2601(6) 0.1767(3) -0.15751(15) 0.0704(8) Uani 1 d . .
H24 H 0.3579 0.2374 -0.1339 0.085 Uiso 1 calc . .
C25 C 0.0430(7) 0.2399(4) -0.18759(19) 0.0999(12) Uani 1 d . .
H25A H -0.0379 0.2743 -0.1558 0.15 Uiso 1 calc . .
H25B H -0.0552 0.1823 -0.2114 0.15 Uiso 1 calc . .
H25C H 0.0846 0.303 -0.2146 0.15 Uiso 1 calc . .
C26 C 0.3930(7) 0.1261(5) -0.20709(17) 0.0994(12) Uani 1 d . .
H26A H 0.5246 0.0817 -0.1878 0.149 Uiso 1 calc . .
H26B H 0.4444 0.1915 -0.2312 0.149 Uiso 1 calc . .
H26C H 0.2946 0.0731 -0.2338 0.149 Uiso 1 calc . .
C23 C 0.2111(6) 0.0761(3) -0.11252(13) 0.0648(7) Uani 1 d . .
H23A H 0.102 0.0201 -0.1348 0.078 Uiso 1 calc . .
H23B H 0.3539 0.032 -0.1007 0.078 Uiso 1 calc . .
C22 C 0.1156(4) 0.1146(2) -0.05330(12) 0.0494(6) Uani 1 d . .
C21 C 0.2458(4) 0.2174(2) -0.01721(12) 0.0480(6) Uani 1 d . .
H21A H 0.2108 0.2929 -0.0393 0.058 Uiso 1 calc . .
H21B H 0.4108 0.2031 -0.0152 0.058 Uiso 1 calc . .
C20 C 0.3293(5) 0.3279(2) 0.08399(16) 0.0649(8) Uani 1 d . .
H20A H 0.4903 0.3088 0.0846 0.097 Uiso 1 calc . .
H20B H 0.2928 0.3325 0.1259 0.097 Uiso 1 calc . .
H20C H 0.297 0.4044 0.0636 0.097 Uiso 1 calc . .
C19 C 0.1833(4) 0.22970(19) 0.04891(12) 0.0456(5) Uani 1 d . .
C18 C 0.4556(4) 0.0564(2) 0.09619(14) 0.0609(7) Uani 1 d . .
H18A H 0.467 -0.0238 0.0785 0.073 Uiso 0.339(16) calc B 1
H18B H 0.5638 0.1095 0.079 0.073 Uiso 0.339(16) calc B 1
H18C H 0.498 0.0083 0.0619 0.073 Uiso 0.661(16) calc B 2
H18D H 0.5658 0.122 0.1047 0.073 Uiso 0.661(16) calc B 2
C9 C 0.0949(5) 0.2522(2) 0.43668(12) 0.0490(6) Uani 1 d . .
C10 C 0.1790(5) 0.2665(3) 0.37329(12) 0.0630(7) Uani 1 d . .
H10A H 0.3341 0.3 0.3799 0.076 Uiso 1 calc . .
H10B H 0.1909 0.1862 0.3557 0.076 Uiso 1 calc . .
C11 C 0.0367(6) 0.3438(3) 0.32528(13) 0.0719(8) Uani 1 d . .
H11 H -0.0303 0.4114 0.3462 0.086 Uiso 1 calc . .
C12 C 0.1918(8) 0.3941(5) 0.2796(2) 0.1129(15) Uani 1 d . .
H12A H 0.0981 0.433 0.2456 0.169 Uiso 1 calc . .
H12B H 0.2771 0.329 0.2638 0.169 Uiso 1 calc . .
H12C H 0.2978 0.4519 0.3005 0.169 Uiso 1 calc . .
C13 C -0.1546(7) 0.2727(5) 0.28887(19) 0.1124(14) Uani 1 d . .
H13A H -0.2401 0.3244 0.2586 0.169 Uiso 1 calc . .
H13B H -0.2563 0.2416 0.3167 0.169 Uiso 1 calc . .
H13C H -0.0898 0.2065 0.2681 0.169 Uiso 1 calc . .
C15 C 0.1047(5) 0.1001(3) 0.14313(13) 0.0610(7) Uani 1 d . .
H15A H 0.0612 0.1805 0.1555 0.073 Uiso 1 calc . .
H15B H -0.0314 0.0487 0.1392 0.073 Uiso 1 calc . .
C14 C 0.2066(4) 0.1055(2) 0.08154(12) 0.0467(5) Uani 1 d . .
C16 C 0.2922(6) 0.0481(4) 0.19065(16) 0.0875(10) Uani 1 d . .
H16A H 0.3021 0.0948 0.2288 0.105 Uiso 0.428(16) calc A 1
H16B H 0.2544 -0.0349 0.2001 0.105 Uiso 0.428(16) calc A 1
H16C H 0.377 0.1122 0.2142 0.105 Uiso 0.572(16) calc A 2
H16D H 0.2266 -0.0055 0.2193 0.105 Uiso 0.572(16) calc A 2
C17A C 0.5085(18) 0.051(3) 0.1667(5) 0.094(7) Uani 0.339(16) d B 1
H17A H 0.5986 -0.0202 0.1794 0.113 Uiso 0.339(16) calc B 1
H17B H 0.5961 0.1224 0.1821 0.113 Uiso 0.339(16) calc B 1
C17B C 0.4455(13) -0.0201(6) 0.1529(3) 0.075(2) Uani 0.661(16) d B 2
H17C H 0.3813 -0.0993 0.1415 0.091 Uiso 0.661(16) calc B 2
H17D H 0.5985 -0.0304 0.1757 0.091 Uiso 0.661(16) calc B 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O1 C1 1.448(3) . ?
O1 O2 1.469(2) . ?
C1 C2 1.530(3) . ?
C1 C5 1.537(3) . ?
C1 C6 1.537(3) . ?
O2 C9 1.453(3) . ?
C2 C3B 1.528(10) . ?
C2 C3A 1.519(15) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C2 H2C 0.97 . ?
C2 H2D 0.97 . ?
O3 C6 1.455(3) . ?
O3 H3 0.76(4) . ?
C3A C4A 1.520(15) . ?
C3A H3AA 0.97 . ?
C3A H3AB 0.97 . ?
C3B C4B 1.546(12) . ?
C3B H3BA 0.97 . ?
C3B H3BB 0.97 . ?
C4A C5 1.482(10) . ?
C4A H4AA 0.97 . ?
C4A H4AB 0.97 . ?
C4B C5 1.529(8) . ?
C4B H4BA 0.97 . ?
C4B H4BB 0.97 . ?
O4 C9 1.396(3) . ?
O4 H4 0.85(3) . ?
C5 H5A 0.97 . ?
C5 H5B 0.97 . ?
C5 H5C 0.97 . ?
C5 H5D 0.97 . ?
O5 C14 1.452(3) . ?
O5 O6 1.463(2) . ?
O6 C22 1.458(3) . ?
C6 C8 1.515(3) . ?
C6 C7 1.525(3) . ?
C7 H7A 0.96 . ?
C7 H7B 0.96 . ?
C7 H7C 0.96 . ?
O7 C19 1.440(3) . ?
O7 H7 0.76(4) . ?
O8 C22 1.390(3) . ?
O8 H8 0.82(5) . ?
C8 C9 1.519(3) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C24 C26 1.508(5) . ?
C24 C25 1.517(4) . ?
C24 C23 1.527(4) . ?
C24 H24 0.98 . ?
C25 H25A 0.96 . ?
C25 H25B 0.96 . ?
C25 H25C 0.96 . ?
C26 H26A 0.96 . ?
C26 H26B 0.96 . ?
C26 H26C 0.96 . ?
C23 C22 1.522(4) . ?
C23 H23A 0.97 . ?
C23 H23B 0.97 . ?
C22 C21 1.524(3) . ?
C21 C19 1.528(3) . ?
C21 H21A 0.97 . ?
C21 H21B 0.97 . ?
C20 C19 1.520(3) . ?
C20 H20A 0.96 . ?
C20 H20B 0.96 . ?
C20 H20C 0.96 . ?
C19 C14 1.540(3) . ?
C18 C17B 1.496(6) . ?
C18 C17A 1.520(11) . ?
C18 C14 1.543(3) . ?
C18 H18A 0.97 . ?
C18 H18B 0.97 . ?
C18 H18C 0.97 . ?
C18 H18D 0.97 . ?
C9 C10 1.523(3) . ?
C10 C11 1.509(4) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 C13 1.502(5) . ?
C11 C12 1.527(5) . ?
C11 H11 0.98 . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C15 C16 1.515(4) . ?
C15 C14 1.528(4) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 C17A 1.423(10) . ?
C16 C17B 1.490(7) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C16 H16C 0.97 . ?
C16 H16D 0.97 . ?
C17A H17A 0.97 . ?
C17A H17B 0.97 . ?
C17B H17C 0.97 . ?
C17B H17D 0.97 . ?

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
C1 O1 O2 109.10(16) . . ?
O1 C1 C2 102.25(19) . . ?
O1 C1 C5 110.4(2) . . ?
C2 C1 C5 105.3(2) . . ?
O1 C1 C6 107.27(18) . . ?
C2 C1 C6 115.23(19) . . ?
C5 C1 C6 115.6(2) . . ?
C9 O2 O1 107.81(15) . . ?
C3B C2 C1 105.2(5) . . ?
C3A C2 C1 105.6(7) . . ?
C3A C2 H2A 110.6 . . ?
C1 C2 H2A 110.6 . . ?
C3A C2 H2B 110.6 . . ?
C1 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?
C3B C2 H2C 110.7 . . ?
C1 C2 H2C 110.7 . . ?
C3B C2 H2D 110.7 . . ?
C1 C2 H2D 110.7 . . ?
H2C C2 H2D 108.8 . . ?
C6 O3 H3 107(3) . . ?
C4A C3A C2 104.7(10) . . ?
C4A C3A H3AA 110.8 . . ?
C2 C3A H3AA 110.8 . . ?
C4A C3A H3AB 110.8 . . ?
C2 C3A H3AB 110.8 . . ?
H3AA C3A H3AB 108.9 . . ?
C2 C3B C4B 101.4(7) . . ?
C2 C3B H3BA 111.5 . . ?
C4B C3B H3BA 111.5 . . ?
C2 C3B H3BB 111.5 . . ?
C4B C3B H3BB 111.5 . . ?
H3BA C3B H3BB 109.3 . . ?
C5 C4A C3A 103.1(10) . . ?
C5 C4A H4AA 111.1 . . ?
C3A C4A H4AA 111.1 . . ?
C5 C4A H4AB 111.1 . . ?
C3A C4A H4AB 111.2 . . ?
H4AA C4A H4AB 109.1 . . ?
C5 C4B C3B 104.5(7) . . ?
C5 C4B H4BA 110.9 . . ?
C3B C4B H4BA 110.9 . . ?
C5 C4B H4BB 110.9 . . ?
C3B C4B H4BB 110.9 . . ?
H4BA C4B H4BB 108.9 . . ?
C9 O4 H4 109(2) . . ?
C4A C5 C1 103.4(5) . . ?
C4B C5 C1 106.6(4) . . ?
C4A C5 H5A 111.1 . . ?
C1 C5 H5A 111.1 . . ?
C4A C5 H5B 111.1 . . ?
C1 C5 H5B 111.1 . . ?
H5A C5 H5B 109 . . ?
C4B C5 H5C 110.4 . . ?
C1 C5 H5C 110.4 . . ?
C4B C5 H5D 110.4 . . ?
C1 C5 H5D 110.4 . . ?
H5C C5 H5D 108.6 . . ?
C14 O5 O6 108.57(16) . . ?
C22 O6 O5 108.62(16) . . ?
O3 C6 C8 108.92(19) . . ?
O3 C6 C7 109.6(2) . . ?
C8 C6 C7 110.6(2) . . ?
O3 C6 C1 104.62(18) . . ?
C8 C6 C1 109.24(18) . . ?
C7 C6 C1 113.7(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C19 O7 H7 110(2) . . ?
C22 O8 H8 109(4) . . ?
C6 C8 C9 114.13(19) . . ?
C6 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C6 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C26 C24 C25 109.9(3) . . ?
C26 C24 C23 109.9(3) . . ?
C25 C24 C23 113.2(3) . . ?
C26 C24 H24 107.9 . . ?
C25 C24 H24 107.9 . . ?
C23 C24 H24 107.9 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C22 C23 C24 116.9(2) . . ?
C22 C23 H23A 108.1 . . ?
C24 C23 H23A 108.1 . . ?
C22 C23 H23B 108.1 . . ?
C24 C23 H23B 108.1 . . ?
H23A C23 H23B 107.3 . . ?
O8 C22 O6 110.4(2) . . ?
O8 C22 C23 110.3(2) . . ?
O6 C22 C23 100.44(19) . . ?
O8 C22 C21 112.6(2) . . ?
O6 C22 C21 106.98(19) . . ?
C23 C22 C21 115.4(2) . . ?
C22 C21 C19 112.60(19) . . ?
C22 C21 H21A 109.1 . . ?
C19 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
C19 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O7 C19 C20 109.9(2) . . ?
O7 C19 C21 108.7(2) . . ?
C20 C19 C21 110.3(2) . . ?
O7 C19 C14 105.10(19) . . ?
C20 C19 C14 113.2(2) . . ?
C21 C19 C14 109.46(18) . . ?
C17B C18 C14 103.4(3) . . ?
C17A C18 C14 106.5(5) . . ?
C17A C18 H18A 110.4 . . ?
C14 C18 H18A 110.4 . . ?
C17A C18 H18B 110.4 . . ?
C14 C18 H18B 110.4 . . ?
H18A C18 H18B 108.6 . . ?
C17B C18 H18C 111.1 . . ?
C14 C18 H18C 111.1 . . ?
C17B C18 H18D 111.1 . . ?
C14 C18 H18D 111.1 . . ?
H18C C18 H18D 109 . . ?
O4 C9 O2 109.47(19) . . ?
O4 C9 C8 112.4(2) . . ?
O2 C9 C8 107.28(19) . . ?
O4 C9 C10 111.1(2) . . ?
O2 C9 C10 103.6(2) . . ?
C8 C9 C10 112.5(2) . . ?
C11 C10 C9 117.9(2) . . ?
C11 C10 H10A 107.8 . . ?
C9 C10 H10A 107.8 . . ?
C11 C10 H10B 107.8 . . ?
C9 C10 H10B 107.8 . . ?
H10A C10 H10B 107.2 . . ?
C13 C11 C10 111.8(3) . . ?
C13 C11 C12 108.1(3) . . ?
C10 C11 C12 109.5(3) . . ?
C13 C11 H11 109.1 . . ?
C10 C11 H11 109.1 . . ?
C12 C11 H11 109.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16 C15 C14 106.3(2) . . ?
C16 C15 H15A 110.5 . . ?
C14 C15 H15A 110.5 . . ?
C16 C15 H15B 110.5 . . ?
C14 C15 H15B 110.5 . . ?
H15A C15 H15B 108.7 . . ?
O5 C14 C15 102.69(19) . . ?
O5 C14 C19 106.87(18) . . ?
C15 C14 C19 114.4(2) . . ?
O5 C14 C18 111.1(2) . . ?
C15 C14 C18 105.5(2) . . ?
C19 C14 C18 115.6(2) . . ?
C17A C16 C15 109.8(5) . . ?
C17B C16 C15 104.4(3) . . ?
C17A C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
C17A C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C17B C16 H16C 110.9 . . ?
C15 C16 H16C 110.9 . . ?
C17B C16 H16D 110.9 . . ?
C15 C16 H16D 110.9 . . ?
H16C C16 H16D 108.9 . . ?
C16 C17A C18 106.9(7) . . ?
C16 C17A H17A 110.3 . . ?
C18 C17A H17A 110.3 . . ?
C16 C17A H17B 110.3 . . ?
C18 C17A H17B 110.3 . . ?
H17A C17A H17B 108.6 . . ?
C16 C17B C18 104.7(4) . . ?
C16 C17B H17C 110.8 . . ?
C18 C17B H17C 110.8 . . ?
C16 C17B H17D 110.8 . . ?
C18 C17B H17D 110.8 . . ?
H17C C17B H17D 108.9 . . ?

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
_geom_torsion_publ_flag
O2 O1 C1 C2 171.60(16) . . . . ?
O2 O1 C1 C5 60.0(2) . . . . ?
O2 O1 C1 C6 -66.8(2) . . . . ?
C1 O1 O2 C9 73.2(2) . . . . ?
O1 C1 C2 C3B -89.1(5) . . . . ?
C5 C1 C2 C3B 26.3(5) . . . . ?
C6 C1 C2 C3B 154.9(5) . . . . ?
O1 C1 C2 C3A -109.5(9) . . . . ?
C5 C1 C2 C3A 5.9(9) . . . . ?
C6 C1 C2 C3A 134.5(9) . . . . ?
C3B C2 C3A C4A -72(3) . . . . ?
C1 C2 C3A C4A 19.6(16) . . . . ?
C3A C2 C3B C4B 54(3) . . . . ?
C1 C2 C3B C4B -40.1(11) . . . . ?
C2 C3A C4A C5 -38.6(18) . . . . ?
C2 C3B C4B C5 38.7(13) . . . . ?
C3A C4A C5 C4B -58.3(15) . . . . ?
C3A C4A C5 C1 42.0(13) . . . . ?
C3B C4B C5 C4A 64.0(14) . . . . ?
C3B C4B C5 C1 -23.1(12) . . . . ?
O1 C1 C5 C4A 79.8(6) . . . . ?
C2 C1 C5 C4A -29.8(6) . . . . ?
C6 C1 C5 C4A -158.2(5) . . . . ?
O1 C1 C5 C4B 107.9(7) . . . . ?
C2 C1 C5 C4B -1.7(7) . . . . ?
C6 C1 C5 C4B -130.1(7) . . . . ?
C14 O5 O6 C22 -73.2(2) . . . . ?
O1 C1 C6 O3 -62.3(2) . . . . ?
C2 C1 C6 O3 50.7(3) . . . . ?
C5 C1 C6 O3 174.1(2) . . . . ?
O1 C1 C6 C8 54.1(2) . . . . ?
C2 C1 C6 C8 167.2(2) . . . . ?
C5 C1 C6 C8 -69.4(3) . . . . ?
O1 C1 C6 C7 178.14(19) . . . . ?
C2 C1 C6 C7 -68.8(3) . . . . ?
C5 C1 C6 C7 54.6(3) . . . . ?
O3 C6 C8 C9 64.4(2) . . . . ?
C7 C6 C8 C9 -175.1(2) . . . . ?
C1 C6 C8 C9 -49.3(3) . . . . ?
C26 C24 C23 C22 169.7(3) . . . . ?
C25 C24 C23 C22 -67.0(4) . . . . ?
O5 O6 C22 O8 -59.4(2) . . . . ?
O5 O6 C22 C23 -175.76(18) . . . . ?
O5 O6 C22 C21 63.5(2) . . . . ?
C24 C23 C22 O8 80.0(3) . . . . ?
C24 C23 C22 O6 -163.5(3) . . . . ?
C24 C23 C22 C21 -48.9(4) . . . . ?
O8 C22 C21 C19 67.1(3) . . . . ?
O6 C22 C21 C19 -54.4(3) . . . . ?
C23 C22 C21 C19 -165.1(2) . . . . ?
C22 C21 C19 O7 -63.2(2) . . . . ?
C22 C21 C19 C20 176.3(2) . . . . ?
C22 C21 C19 C14 51.1(3) . . . . ?
O1 O2 C9 O4 59.7(2) . . . . ?
O1 O2 C9 C8 -62.5(2) . . . . ?
O1 O2 C9 C10 178.28(17) . . . . ?
C6 C8 C9 O4 -66.8(3) . . . . ?
C6 C8 C9 O2 53.6(3) . . . . ?
C6 C8 C9 C10 166.9(2) . . . . ?
O4 C9 C10 C11 45.8(3) . . . . ?
O2 C9 C10 C11 -71.7(3) . . . . ?
C8 C9 C10 C11 172.8(2) . . . . ?
C9 C10 C11 C13 -86.0(3) . . . . ?
C9 C10 C11 C12 154.3(3) . . . . ?
O6 O5 C14 C15 -172.48(16) . . . . ?
O6 O5 C14 C19 66.8(2) . . . . ?
O6 O5 C14 C18 -60.2(2) . . . . ?
C16 C15 C14 O5 115.9(3) . . . . ?
C16 C15 C14 C19 -128.7(3) . . . . ?
C16 C15 C14 C18 -0.5(3) . . . . ?
O7 C19 C14 O5 60.8(2) . . . . ?
C20 C19 C14 O5 -179.3(2) . . . . ?
C21 C19 C14 O5 -55.8(2) . . . . ?
O7 C19 C14 C15 -52.2(3) . . . . ?
C20 C19 C14 C15 67.8(3) . . . . ?
C21 C19 C14 C15 -168.7(2) . . . . ?
O7 C19 C14 C18 -175.0(2) . . . . ?
C20 C19 C14 C18 -55.1(3) . . . . ?
C21 C19 C14 C18 68.4(3) . . . . ?
C17B C18 C14 O5 -87.0(4) . . . . ?
C17A C18 C14 O5 -123.1(11) . . . . ?
C17B C18 C14 C15 23.5(4) . . . . ?
C17A C18 C14 C15 -12.6(11) . . . . ?
C17B C18 C14 C19 151.0(4) . . . . ?
C17A C18 C14 C19 114.9(11) . . . . ?
C14 C15 C16 C17A 14.5(13) . . . . ?
C14 C15 C16 C17B -22.9(4) . . . . ?
C17B C16 C17A C18 64.9(12) . . . . ?
C15 C16 C17A C18 -22.6(19) . . . . ?
C17B C18 C17A C16 -68.1(11) . . . . ?
C14 C18 C17A C16 21.8(19) . . . . ?
C17A C16 C17B C18 -65.4(8) . . . . ?
C15 C16 C17B C18 38.5(6) . . . . ?
C17A C18 C17B C16 61.3(8) . . . . ?
C14 C18 C17B C16 -38.4(6) . . . . ?
#----------------------------------------------------------------------------#
#                        END OF CIF                                          #
#----------------------------------------------------------------------------#
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mvt_434-3_2_1568

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_database_code_depnum_ccdc_archive 'CCDC 1411166'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-11-13 downloaded from the CCDC.
;

_audit_creation_date             2013-10-30T13:21:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_chemical_name_systematic        
;
8-cyclopropyl-10-methyl-6,7-dioxaspiro[4.5]decane-8,10-diol
;
_chemical_formula_moiety         'C12 H20 O4'
_chemical_formula_sum            'C12 H20 O4'
_chemical_formula_weight         228.28
_chemical_melting_point          379.0(10)
_chemical_compound_source        synthetic
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.8134(4)
_cell_length_b                   10.7208(7)
_cell_length_c                   19.8086(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1234.56(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    1348
_cell_measurement_theta_min      3.614
_cell_measurement_theta_max      26.484

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.015
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_F_000             496
_exptl_special_details           
;
Recrystallized from petrol-ether
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm using CrysAlisPro 
 (Agilent Technologies,2013).
;
_exptl_absorpt_correction_T_min  0.55655
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.999

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) (Agilent Technologies)'
_diffrn_source_current           50
_diffrn_source_voltage           40
_diffrn_source_power             1.6
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Sapphire3 (Agilent Technologies)'
_diffrn_detector_area_resol_mean 16.328
_diffrn_measurement_specimen_support 'glass fiber'
_diffrn_radiation_collimation    '0.8 mm'
_diffrn_orient_matrix_ub_11      0.0957969
_diffrn_orient_matrix_ub_12      -0.0330383
_diffrn_orient_matrix_ub_13      0.013108
_diffrn_orient_matrix_ub_21      -0.0351241
_diffrn_orient_matrix_ub_22      0.015087
_diffrn_orient_matrix_ub_23      0.0333079
_diffrn_orient_matrix_ub_31      -0.0669055
_diffrn_orient_matrix_ub_32      -0.0552568
_diffrn_orient_matrix_ub_33      0.0012801
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Gemini S (Agilent Technologies)'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_number            5900
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.624
_diffrn_reflns_theta_max         28.818
_diffrn_reflns_theta_full        26.32
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.923
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.857
_reflns_number_total             2770
_reflns_number_gt                2017
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2013)'
_computing_structure_solution    
; SUPERFLIP (Palatinus L. and Chapuis G., 2007) and 
  EDMA (Van Smaalen et al, 2003)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   iterative
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0471P)²+0.0841P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2770
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1115
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.15
_refine_diff_density_rms         0.029

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1' C 0.7473(6) 0.3203(3) 0.11798(15) 0.0680(9) Uani 1 d . .
H1' H 0.9131 0.304 0.1188 0.082 Uiso 1 calc . .
C1 C 0.5910(5) 0.2893(3) 0.39891(13) 0.0554(7) Uani 1 d . .
H1A H 0.5633 0.3689 0.4207 0.067 Uiso 1 calc . .
H1B H 0.4453 0.2462 0.3939 0.067 Uiso 1 calc . .
H9 H 0.427(6) 0.543(3) 0.3014(17) 0.087(12) Uiso 1 d . .
C2' C 0.6175(9) 0.2547(4) 0.06364(18) 0.1065(15) Uani 1 d . .
H2'A H 0.7027 0.1993 0.0341 0.128 Uiso 1 calc . .
H2'B H 0.4612 0.2288 0.0733 0.128 Uiso 1 calc . .
C2 C 0.7550(7) 0.2124(4) 0.43975(19) 0.0883(11) Uani 1 d . .
H2A H 0.8318 0.2639 0.4731 0.106 Uiso 1 calc . .
H2B H 0.6733 0.1463 0.463 0.106 Uiso 1 calc . .
H8 H 0.355(7) 0.388(4) 0.215(2) 0.091(15) Uiso 1 d . .
C3' C 0.6645(9) 0.3905(4) 0.05869(17) 0.0981(13) Uani 1 d . .
H3'A H 0.7777 0.4178 0.0259 0.118 Uiso 1 calc . .
H3'B H 0.5363 0.4472 0.0652 0.118 Uiso 1 calc . .
C3 C 0.9258(6) 0.1588(3) 0.39189(16) 0.0719(9) Uani 1 d . .
H3A H 0.8705 0.0809 0.373 0.086 Uiso 1 calc . .
H3B H 1.0718 0.1441 0.4142 0.086 Uiso 1 calc . .
C4 C 0.9495(5) 0.2575(3) 0.33756(14) 0.0567(7) Uani 1 d . .
H4A H 1.0035 0.2213 0.2956 0.068 Uiso 1 calc . .
H4B H 1.0554 0.3226 0.3514 0.068 Uiso 1 calc . .
C5 C 0.7048(4) 0.3089(2) 0.32982(13) 0.0439(6) Uani 1 d . .
C8 C 0.6378(5) 0.3393(2) 0.18604(13) 0.0499(6) Uani 1 d . .
O8 O 0.4026(4) 0.3605(2) 0.17917(12) 0.0644(6) Uani 1 d . .
O7 O 0.6776(3) 0.22139(15) 0.21952(9) 0.0539(5) Uani 1 d . .
O6 O 0.5704(3) 0.22704(14) 0.28665(8) 0.0494(4) Uani 1 d . .
C9 C 0.7570(4) 0.4404(2) 0.22715(14) 0.0464(6) Uani 1 d . .
H9A H 0.7222 0.5211 0.2075 0.056 Uiso 1 calc . .
H9B H 0.9221 0.4282 0.2245 0.056 Uiso 1 calc . .
O9 O 0.4411(3) 0.46989(18) 0.30483(10) 0.0534(5) Uani 1 d . .
C11 C 0.8219(5) 0.5370(3) 0.34043(16) 0.0609(8) Uani 1 d . .
H11A H 0.9832 0.5202 0.3353 0.091 Uiso 1 calc . .
H11B H 0.7813 0.5328 0.3873 0.091 Uiso 1 calc . .
H11C H 0.7883 0.6188 0.3234 0.091 Uiso 1 calc . .
C10 C 0.6847(4) 0.4411(2) 0.30140(13) 0.0442(6) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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' C3' 1.476(5) . ?
C1' C2' 1.491(5) . ?
C1' C8 1.504(4) . ?
C1' H1' 0.98 . ?
C1 C2 1.498(4) . ?
C1 C5 1.534(4) . ?
C1 H1A 0.97 . ?
C1 H1B 0.97 . ?
C2' C3' 1.484(6) . ?
C2' H2'A 0.97 . ?
C2' H2'B 0.97 . ?
C2 C3 1.488(5) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3' H3'A 0.97 . ?
C3' H3'B 0.97 . ?
C3 C4 1.515(4) . ?
C3 H3A 0.97 . ?
C3 H3B 0.97 . ?
C4 C5 1.533(3) . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C5 O6 1.453(3) . ?
C5 C10 1.529(3) . ?
C8 O8 1.393(3) . ?
C8 O7 1.446(3) . ?
C8 C9 1.523(4) . ?
O8 H8 0.81(4) . ?
O7 O6 1.470(2) . ?
C9 C10 1.530(4) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
O9 C10 1.451(3) . ?
O9 H9 0.79(3) . ?
C11 C10 1.514(4) . ?
C11 H11A 0.96 . ?
C11 H11B 0.96 . ?
C11 H11C 0.96 . ?

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
C3' C1' C2' 60.0(2) . . ?
C3' C1' C8 120.4(3) . . ?
C2' C1' C8 119.8(3) . . ?
C3' C1' H1' 115.2 . . ?
C2' C1' H1' 115.2 . . ?
C8 C1' H1' 115.2 . . ?
C2 C1 C5 106.4(2) . . ?
C2 C1 H1A 110.4 . . ?
C5 C1 H1A 110.4 . . ?
C2 C1 H1B 110.4 . . ?
C5 C1 H1B 110.4 . . ?
H1A C1 H1B 108.6 . . ?
C3' C2' C1' 59.5(2) . . ?
C3' C2' H2'A 117.8 . . ?
C1' C2' H2'A 117.8 . . ?
C3' C2' H2'B 117.8 . . ?
C1' C2' H2'B 117.8 . . ?
H2'A C2' H2'B 115 . . ?
C3 C2 C1 107.0(3) . . ?
C3 C2 H2A 110.3 . . ?
C1 C2 H2A 110.3 . . ?
C3 C2 H2B 110.3 . . ?
C1 C2 H2B 110.3 . . ?
H2A C2 H2B 108.6 . . ?
C1' C3' C2' 60.5(2) . . ?
C1' C3' H3'A 117.7 . . ?
C2' C3' H3'A 117.7 . . ?
C1' C3' H3'B 117.7 . . ?
C2' C3' H3'B 117.7 . . ?
H3'A C3' H3'B 114.8 . . ?
C2 C3 C4 104.1(3) . . ?
C2 C3 H3A 110.9 . . ?
C4 C3 H3A 110.9 . . ?
C2 C3 H3B 110.9 . . ?
C4 C3 H3B 110.9 . . ?
H3A C3 H3B 109 . . ?
C3 C4 C5 103.7(2) . . ?
C3 C4 H4A 111 . . ?
C5 C4 H4A 111 . . ?
C3 C4 H4B 111 . . ?
C5 C4 H4B 111 . . ?
H4A C4 H4B 109 . . ?
O6 C5 C10 107.6(2) . . ?
O6 C5 C4 109.9(2) . . ?
C10 C5 C4 116.1(2) . . ?
O6 C5 C1 102.17(19) . . ?
C10 C5 C1 115.0(2) . . ?
C4 C5 C1 105.2(2) . . ?
O8 C8 O7 110.2(2) . . ?
O8 C8 C1' 110.5(3) . . ?
O7 C8 C1' 103.0(2) . . ?
O8 C8 C9 112.5(2) . . ?
O7 C8 C9 107.7(2) . . ?
C1' C8 C9 112.5(2) . . ?
C8 O8 H8 108(3) . . ?
C8 O7 O6 108.13(16) . . ?
C5 O6 O7 109.23(16) . . ?
C8 C9 C10 113.1(2) . . ?
C8 C9 H9A 109 . . ?
C10 C9 H9A 109 . . ?
C8 C9 H9B 109 . . ?
C10 C9 H9B 109 . . ?
H9A C9 H9B 107.8 . . ?
C10 O9 H9 108(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O9 C10 C11 110.2(2) . . ?
O9 C10 C5 104.76(19) . . ?
C11 C10 C5 113.7(2) . . ?
O9 C10 C9 108.3(2) . . ?
C11 C10 C9 110.4(2) . . ?
C5 C10 C9 109.19(19) . . ?

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
_geom_torsion_publ_flag
C8 C1' C2' C3' 110.1(4) . . . . ?
C5 C1 C2 C3 -15.0(4) . . . . ?
C8 C1' C3' C2' -109.1(4) . . . . ?
C1 C2 C3 C4 32.6(4) . . . . ?
C2 C3 C4 C5 -37.1(3) . . . . ?
C3 C4 C5 O6 -81.6(3) . . . . ?
C3 C4 C5 C10 156.0(2) . . . . ?
C3 C4 C5 C1 27.7(3) . . . . ?
C2 C1 C5 O6 106.6(3) . . . . ?
C2 C1 C5 C10 -137.2(3) . . . . ?
C2 C1 C5 C4 -8.2(3) . . . . ?
C3' C1' C8 O8 35.4(4) . . . . ?
C2' C1' C8 O8 -35.3(4) . . . . ?
C3' C1' C8 O7 153.0(3) . . . . ?
C2' C1' C8 O7 82.4(4) . . . . ?
C3' C1' C8 C9 -91.2(4) . . . . ?
C2' C1' C8 C9 -161.9(3) . . . . ?
O8 C8 O7 O6 -60.3(2) . . . . ?
C1' C8 O7 O6 -178.2(2) . . . . ?
C9 C8 O7 O6 62.7(2) . . . . ?
C10 C5 O6 O7 66.3(2) . . . . ?
C4 C5 O6 O7 -61.0(2) . . . . ?
C1 C5 O6 O7 -172.29(17) . . . . ?
C8 O7 O6 C5 -72.2(2) . . . . ?
O8 C8 C9 C10 67.4(3) . . . . ?
O7 C8 C9 C10 -54.2(3) . . . . ?
C1' C8 C9 C10 -167.1(2) . . . . ?
O6 C5 C10 O9 61.1(2) . . . . ?
C4 C5 C10 O9 -175.3(2) . . . . ?
C1 C5 C10 O9 -51.9(3) . . . . ?
O6 C5 C10 C11 -178.5(2) . . . . ?
C4 C5 C10 C11 -54.9(3) . . . . ?
C1 C5 C10 C11 68.5(3) . . . . ?
O6 C5 C10 C9 -54.7(2) . . . . ?
C4 C5 C10 C9 68.9(3) . . . . ?
C1 C5 C10 C9 -167.8(2) . . . . ?
C8 C9 C10 O9 -63.4(3) . . . . ?
C8 C9 C10 C11 175.8(2) . . . . ?
C8 C9 C10 C5 50.1(3) . . . . ?

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
O9 H9 O7 0.79(3) 2.05(4) 2.825(2) 167(4) 3_655
O8 H8 O9 0.81(4) 2.05(4) 2.760(3) 146(4) .


#----------------------------------------------------------------------------#
#                        END OF CIF                                          #
#----------------------------------------------------------------------------#
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mvt_435_k_1566

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_database_code_depnum_ccdc_archive 'CCDC 1411167'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-11-13 downloaded from the CCDC.
;

_audit_creation_date             2013-10-27T18:04:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_chemical_name_systematic        
;
10-methyl-8-phenyl-6,7-dioxaspiro[4.5]decane-8,10-diol
;
_chemical_formula_moiety         'C15 H20 O4'
_chemical_formula_sum            'C15 H20 O4'
_chemical_formula_weight         264.31
_chemical_melting_point          398(1)
_chemical_compound_source        synthetic

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.1244(3)
_cell_length_b                   14.5321(5)
_cell_length_c                   21.2515(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2817.89(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4170
_cell_measurement_theta_min      3.893
_cell_measurement_theta_max      29.063

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_F_000             1136
_exptl_special_details           
; Recrystallized from petrol-ether
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm using CrysAlisPro 
 (Agilent Technologies, 2013).
;
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.993

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) (Agilent Technologies)'
_diffrn_source_current           50
_diffrn_source_voltage           40
_diffrn_source_power             2
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 16.328
_diffrn_measurement_specimen_support 'glass fiber'
_diffrn_radiation_collimation    '0.8 mm'
_diffrn_orient_matrix_ub_11      -0.0024693
_diffrn_orient_matrix_ub_12      -0.0092365
_diffrn_orient_matrix_ub_13      0.0327583
_diffrn_orient_matrix_ub_21      0.0320886
_diffrn_orient_matrix_ub_22      0.0435489
_diffrn_orient_matrix_ub_23      0.0061841
_diffrn_orient_matrix_ub_31      -0.0707843
_diffrn_orient_matrix_ub_32      0.0199947
_diffrn_orient_matrix_ub_33      0.0016548
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Gemini S (Agilent Technologies)'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.03
_diffrn_reflns_number            16276
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         28.937
_diffrn_reflns_theta_full        26.32
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.903
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.903
_reflns_number_total             3363
_reflns_number_gt                2562
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2013)'
_computing_structure_solution    
; SUPERFLIP (Palatinus and Chapuis, 2007) and 
  EDMA (Van Smaalen et al, 2003)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   iterative
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0486P)²+0.7662P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3363
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1159
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.031

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1' C -0.05041(15) 0.24260(9) 0.17490(6) 0.0407(3) Uani 1 d . .
C1 C 0.30177(19) -0.06006(10) 0.09967(8) 0.0540(4) Uani 1 d . .
H1A H 0.4072 -0.0532 0.1032 0.065 Uiso 1 calc . .
H1B H 0.2676 -0.0999 0.1332 0.065 Uiso 1 calc . .
C2' C -0.03978(18) 0.31025(10) 0.22100(8) 0.0519(4) Uani 1 d . .
H2' H 0.0291 0.3042 0.253 0.062 Uiso 1 calc . .
C2 C 0.2597(3) -0.09866(12) 0.03554(9) 0.0714(5) Uani 1 d . .
H2A H 0.3331 -0.1417 0.0206 0.086 Uiso 1 calc . .
H2B H 0.1657 -0.1298 0.0375 0.086 Uiso 1 calc . .
C3' C -0.1305(2) 0.38613(12) 0.21973(9) 0.0644(5) Uani 1 d . .
H3' H -0.122 0.431 0.2507 0.077 Uiso 1 calc . .
C3 C 0.2516(2) -0.01642(13) -0.00639(8) 0.0681(5) Uani 1 d . .
H3A H 0.1892 -0.0286 -0.0424 0.082 Uiso 1 calc . .
H3B H 0.3484 0.0004 -0.0214 0.082 Uiso 1 calc . .
C4' C -0.2328(2) 0.39578(12) 0.17319(10) 0.0675(5) Uani 1 d . .
H4' H -0.2938 0.447 0.1725 0.081 Uiso 1 calc . .
C4 C 0.18792(19) 0.05920(11) 0.03383(7) 0.0516(4) Uani 1 d . .
H4A H 0.0826 0.0628 0.0281 0.062 Uiso 1 calc . .
H4B H 0.2307 0.1181 0.0227 0.062 Uiso 1 calc . .
C5 C 0.22508(15) 0.03429(9) 0.10259(6) 0.0400(3) Uani 1 d . .
C5' C -0.2451(2) 0.32986(13) 0.12762(9) 0.0688(5) Uani 1 d . .
H5' H -0.3159 0.336 0.0964 0.083 Uiso 1 calc . .
C9 C 0.20695(14) 0.19064(9) 0.14974(6) 0.0379(3) Uani 1 d . .
H9A H 0.2538 0.234 0.178 0.046 Uiso 1 calc . .
H9B H 0.1923 0.2212 0.1097 0.046 Uiso 1 calc . .
H9 H 0.268(2) 0.0722(14) 0.2230(9) 0.075(6) Uiso 1 d . .
O9 O 0.34679(11) 0.06939(7) 0.20044(5) 0.0455(3) Uani 1 d . .
C8 C 0.05824(14) 0.16352(9) 0.17681(6) 0.0365(3) Uani 1 d . .
H8 H 0.003(2) 0.1133(12) 0.2540(9) 0.063(5) Uiso 1 d . .
O8 O 0.08382(11) 0.13129(7) 0.23789(4) 0.0433(3) Uani 1 d . .
O7 O -0.00599(10) 0.09313(6) 0.13807(5) 0.0418(2) Uani 1 d . .
C6' C -0.15274(19) 0.25358(11) 0.12746(8) 0.0563(4) Uani 1 d . .
H6' H -0.1598 0.2101 0.0955 0.068 Uiso 1 calc . .
O6 O 0.09257(11) 0.01300(6) 0.13768(5) 0.0432(2) Uani 1 d . .
C10 C 0.30799(15) 0.10810(9) 0.14020(6) 0.0392(3) Uani 1 d . .
C11 C 0.45203(18) 0.13727(12) 0.10992(9) 0.0599(4) Uani 1 d . .
H11A H 0.4965 0.1849 0.1347 0.09 Uiso 1 calc . .
H11B H 0.4335 0.1599 0.0682 0.09 Uiso 1 calc . .
H11C H 0.5169 0.0854 0.1077 0.09 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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' C6' 1.383(2) . ?
C1' C2' 1.391(2) . ?
C1' C8 1.5182(19) . ?
C1 C2 1.523(2) . ?
C1 C5 1.5406(19) . ?
C1 H1A 0.97 . ?
C1 H1B 0.97 . ?
C2' C3' 1.379(2) . ?
C2' H2' 0.93 . ?
C2 C3 1.492(3) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3' C4' 1.367(3) . ?
C3' H3' 0.93 . ?
C3 C4 1.509(2) . ?
C3 H3A 0.97 . ?
C3 H3B 0.97 . ?
C4' C5' 1.367(3) . ?
C4' H4' 0.93 . ?
C4 C5 1.5432(19) . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C5 O6 1.4539(17) . ?
C5 C10 1.5367(19) . ?
C5' C6' 1.393(2) . ?
C5' H5' 0.93 . ?
C9 C8 1.5255(18) . ?
C9 C10 1.5264(19) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
O9 C10 1.4425(16) . ?
O9 H9 0.87(2) . ?
C8 O8 1.3997(15) . ?
C8 O7 1.4380(15) . ?
O8 H8 0.85(2) . ?
O7 O6 1.4713(13) . ?
C6' H6' 0.93 . ?
C10 C11 1.524(2) . ?
C11 H11A 0.96 . ?
C11 H11B 0.96 . ?
C11 H11C 0.96 . ?

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
C6' C1' C2' 118.60(14) . . ?
C6' C1' C8 123.19(13) . . ?
C2' C1' C8 118.07(13) . . ?
C2 C1 C5 104.44(13) . . ?
C2 C1 H1A 110.9 . . ?
C5 C1 H1A 110.9 . . ?
C2 C1 H1B 110.9 . . ?
C5 C1 H1B 110.9 . . ?
H1A C1 H1B 108.9 . . ?
C3' C2' C1' 120.64(16) . . ?
C3' C2' H2' 119.7 . . ?
C1' C2' H2' 119.7 . . ?
C3 C2 C1 104.58(14) . . ?
C3 C2 H2A 110.8 . . ?
C1 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C4' C3' C2' 120.39(17) . . ?
C4' C3' H3' 119.8 . . ?
C2' C3' H3' 119.8 . . ?
C2 C3 C4 105.31(14) . . ?
C2 C3 H3A 110.7 . . ?
C4 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
C4 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
C5' C4' C3' 119.79(16) . . ?
C5' C4' H4' 120.1 . . ?
C3' C4' H4' 120.1 . . ?
C3 C4 C5 106.31(13) . . ?
C3 C4 H4A 110.5 . . ?
C5 C4 H4A 110.5 . . ?
C3 C4 H4B 110.5 . . ?
C5 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
O6 C5 C10 106.93(10) . . ?
O6 C5 C1 102.07(11) . . ?
C10 C5 C1 114.75(12) . . ?
O6 C5 C4 110.66(12) . . ?
C10 C5 C4 115.90(12) . . ?
C1 C5 C4 105.69(12) . . ?
C4' C5' C6' 120.65(17) . . ?
C4' C5' H5' 119.7 . . ?
C6' C5' H5' 119.7 . . ?
C8 C9 C10 112.61(10) . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C10 O9 H9 105.5(13) . . ?
O8 C8 O7 111.15(10) . . ?
O8 C8 C1' 112.76(11) . . ?
O7 C8 C1' 104.89(10) . . ?
O8 C8 C9 106.73(11) . . ?
O7 C8 C9 109.30(10) . . ?
C1' C8 C9 112.04(11) . . ?
C8 O8 H8 109.4(13) . . ?
C8 O7 O6 108.49(9) . . ?
C1' C6' C5' 119.91(16) . . ?
C1' C6' H6' 120 . . ?
C5' C6' H6' 120 . . ?
C5 O6 O7 110.05(9) . . ?
O9 C10 C11 105.76(12) . . ?
O9 C10 C9 109.67(11) . . ?
C11 C10 C9 111.01(12) . . ?
O9 C10 C5 108.07(10) . . ?
C11 C10 C5 113.54(12) . . ?
C9 C10 C5 108.68(11) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
_geom_torsion_publ_flag
C6' C1' C2' C3' 0.7(2) . . . . ?
C8 C1' C2' C3' 176.59(14) . . . . ?
C5 C1 C2 C3 34.4(2) . . . . ?
C1' C2' C3' C4' 0.3(3) . . . . ?
C1 C2 C3 C4 -37.1(2) . . . . ?
C2' C3' C4' C5' -0.1(3) . . . . ?
C2 C3 C4 C5 25.1(2) . . . . ?
C2 C1 C5 O6 97.21(15) . . . . ?
C2 C1 C5 C10 -147.55(14) . . . . ?
C2 C1 C5 C4 -18.57(17) . . . . ?
C3 C4 C5 O6 -113.42(14) . . . . ?
C3 C4 C5 C10 124.63(15) . . . . ?
C3 C4 C5 C1 -3.67(17) . . . . ?
C3' C4' C5' C6' -1.1(3) . . . . ?
C6' C1' C8 O8 -142.88(14) . . . . ?
C2' C1' C8 O8 41.41(17) . . . . ?
C6' C1' C8 O7 -21.78(18) . . . . ?
C2' C1' C8 O7 162.51(12) . . . . ?
C6' C1' C8 C9 96.69(16) . . . . ?
C2' C1' C8 C9 -79.03(15) . . . . ?
C10 C9 C8 O8 66.61(13) . . . . ?
C10 C9 C8 O7 -53.69(14) . . . . ?
C10 C9 C8 C1' -169.51(11) . . . . ?
O8 C8 O7 O6 -57.44(12) . . . . ?
C1' C8 O7 O6 -179.59(9) . . . . ?
C9 C8 O7 O6 60.10(12) . . . . ?
C2' C1' C6' C5' -1.8(2) . . . . ?
C8 C1' C6' C5' -177.52(15) . . . . ?
C4' C5' C6' C1' 2.1(3) . . . . ?
C10 C5 O6 O7 66.79(12) . . . . ?
C1 C5 O6 O7 -172.38(10) . . . . ?
C4 C5 O6 O7 -60.29(13) . . . . ?
C8 O7 O6 C5 -69.95(12) . . . . ?
C8 C9 C10 O9 -66.51(14) . . . . ?
C8 C9 C10 C11 176.98(12) . . . . ?
C8 C9 C10 C5 51.43(14) . . . . ?
O6 C5 C10 O9 62.18(13) . . . . ?
C1 C5 C10 O9 -50.21(15) . . . . ?
C4 C5 C10 O9 -173.91(12) . . . . ?
O6 C5 C10 C11 179.16(12) . . . . ?
C1 C5 C10 C11 66.77(17) . . . . ?
C4 C5 C10 C11 -56.92(17) . . . . ?
O6 C5 C10 C9 -56.78(13) . . . . ?
C1 C5 C10 C9 -169.17(12) . . . . ?
C4 C5 C10 C9 67.14(15) . . . . ?

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
O9 H9 O8 0.87(2) 1.91(2) 2.6832(15) 147.5(19) .
O8 H8 O9 0.85(2) 1.84(2) 2.6841(14) 171.0(18) 6_556
#----------------------------------------------------------------------------#
#                        END OF CIF                                          #
#----------------------------------------------------------------------------#
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_chemical_properties_physical    Heat-sensitive
