# 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_4,
_database_code_depnum_ccdc_archive 'CCDC 1060373'
_audit_update_record             
;
2015-04-18 deposited with the CCDC.
2015-05-14 downloaded from the CCDC.
;
_audit_creation_date             2015-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            '4, 5-seco-probotryenol A'
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H26 O2, H2 O'
_chemical_formula_sum            'C15 H28 O3'
_chemical_formula_weight         256.37
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.30805(13)
_cell_length_b                   14.8331(3)
_cell_length_c                   16.7092(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1563.44(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6716
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      62.8680
_cell_measurement_theta_min      3.9680
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.089
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12848
_diffrn_reflns_theta_full        62.77
_diffrn_reflns_theta_max         62.77
_diffrn_reflns_theta_min         3.99
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector_area_resol_mean 16.0288
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -102.00  -27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184  -37.0000 -120.0000 75

#__ type_ start__ end____ width___ exp.time_
  2 omega   35.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184 -178.0000   90.0000 46

#__ type_ start__ end____ width___ exp.time_
  3 omega   30.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000 -150.0000 72

#__ type_ start__ end____ width___ exp.time_
  4 omega   28.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   83.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -77.0000  150.0000 33

#__ type_ start__ end____ width___ exp.time_
  6 omega   23.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000 -180.0000 46

#__ type_ start__ end____ width___ exp.time_
  7 omega   28.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000  -30.0000 43

#__ type_ start__ end____ width___ exp.time_
  8 omega   67.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000   30.0000 32

#__ type_ start__ end____ width___ exp.time_
  9 omega  102.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000   30.0000 49

#__ type_ start__ end____ width___ exp.time_
 10 omega   21.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -77.0000  150.0000 28

#__ type_ start__ end____ width___ exp.time_
 11 omega   55.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 12 omega   60.00  124.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  -30.0000 64

#__ type_ start__ end____ width___ exp.time_
 13 omega  128.00  160.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
 14 omega   62.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  -60.0000 33

#__ type_ start__ end____ width___ exp.time_
 15 omega  123.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   35.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  178.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
 17 omega   25.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000   30.0000 31

#__ type_ start__ end____ width___ exp.time_
 18 omega   22.00   48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega  105.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000    0.0000 46

#__ type_ start__ end____ width___ exp.time_
 20 omega -110.00  -53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184  178.0000    0.0000 57

#__ type_ start__ end____ width___ exp.time_
 21 omega -109.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184 -178.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
 22 omega   12.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   53.0000   94.0000 91

#__ type_ start__ end____ width___ exp.time_
 23 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000    0.0000 89

#__ type_ start__ end____ width___ exp.time_
 24 omega -134.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  -77.0000 -180.0000 100

#__ type_ start__ end____ width___ exp.time_
 25 omega   69.00  160.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   53.0000   94.0000 91

#__ type_ start__ end____ width___ exp.time_
 26 omega   19.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 27 omega   19.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000   90.0000 64

#__ type_ start__ end____ width___ exp.time_
 28 omega   60.00  161.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  120.0000 101

#__ type_ start__ end____ width___ exp.time_
 29 omega   61.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000 -150.0000 102

#__ type_ start__ end____ width___ exp.time_
 30 omega   18.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000   30.0000 72

#__ type_ start__ end____ width___ exp.time_
 31 omega   60.00  161.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000 -120.0000 101
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1452575000
_diffrn_orient_matrix_UB_12      0.0729032000
_diffrn_orient_matrix_UB_13      -0.0361534000
_diffrn_orient_matrix_UB_21      -0.0571118000
_diffrn_orient_matrix_UB_22      0.0327768000
_diffrn_orient_matrix_UB_23      0.0847972000
_diffrn_orient_matrix_UB_31      0.1877767000
_diffrn_orient_matrix_UB_32      0.0663293000
_diffrn_orient_matrix_UB_33      -0.0021655000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2417
_reflns_number_total             2512
_reflns_odcompleteness_completeness 91.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.105
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(18)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2512
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0281
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0360P)²+0.1930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0708
_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. 
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H2(0.041) H3C(0.055) H3D(0.055) H1(0.051) H2A(0.033) H7A(0.033)
 H7B(0.033) H3A(0.033) H3B(0.033) H14A(0.042) H14B(0.042) H14C(0.042) H15(0.03)
 H1A(0.031) H10A(0.036) H10B(0.036) H12A(0.053) H12B(0.053) H12C(0.053)
 H5(0.031) H4A(0.035) H4B(0.035) H13A(0.055) H13B(0.055) H13C(0.055)
 H11A(0.079) H11B(0.079) H11C(0.079)
 Fixed X: H2(-0.2967) H3C(-0.4509) H3D(-0.3072) H1(0.6091) H2A(0.297) H7A(-
 0.4278) H7B(-0.2467) H3A(0.1987) H3B(0.1482) H14A(0.0489) H14B(0.1767)
 H14C(0.1372) H15(-0.3615) H1A(-0.1237) H10A(0.055) H10B(-0.1494) H12A(-0.555)
 H12B(-0.4769) H12C(-0.5748) H5(-0.1582) H4A(0.4991) H4B(0.5595) H13A(0.0031)
 H13B(-0.1155) H13C(-0.2021) H11A(0.4013) H11B(0.2296) H11C(0.1671)
 Fixed Y: H2(-0.2558) H3C(-0.2157) H3D(-0.1939) H1(0.1778) H2A(-0.0517) H7A(-
 0.022) H7B(-0.0016) H3A(0.0981) H3B(0.0695) H14A(-0.1148) H14B(-0.1041) H14C(-
 0.0201) H15(-0.1291) H1A(-0.0396) H10A(-0.1826) H10B(-0.1851) H12A(0.1454)
 H12B(0.2004) H12C(0.1041) H5(0.1304) H4A(0.043) H4B(0.0528) H13A(0.1319)
 H13B(0.2174) H13C(0.1665) H11A(-0.1009) H11B(-0.1673) H11C(-0.0955)
 Fixed Z: H2(-0.886) H3C(-1.0752) H3D(-1.0153) H1(-0.6328) H2A(-0.7645) H7A(-
 0.937) H7B(-0.9994) H3A(-0.7341) H3B(-0.6458) H14A(-0.9825) H14B(-0.9026)
 H14C(-0.9575) H15(-0.835) H1A(-0.7037) H10A(-0.7905) H10B(-0.7362) H12A(-
 0.9545) H12B(-0.8801) H12C(-0.8685) H5(-0.7914) H4A(-0.6193) H4B(-0.7101)
 H13A(-0.9733) H13B(-0.941) H13C(-1.0164) H11A(-0.6382) H11B(-0.6718) H11C(-
 0.6072)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
_atom_site_refinement_flags_posn
O2 O -0.21329(16) -0.21809(6) -0.90316(6) 0.0273(2) Uani 1 d . . .
H2 H -0.2967 -0.2558 -0.8860 0.041 Uiso 1 calc . . GR
O3 O -0.34124(17) -0.18495(7) -1.06391(6) 0.0366(3) Uani 1 d . . .
H3C H -0.4509 -0.2157 -1.0752 0.055 Uiso 1 d . . G
H3D H -0.3072 -0.1939 -1.0153 0.055 Uiso 1 d . . G
O1 O 0.49828(17) 0.16952(6) -0.65733(6) 0.0339(3) Uani 1 d . . .
H1 H 0.6091 0.1778 -0.6328 0.051 Uiso 1 calc . . GR
C2 C 0.2020(2) -0.03991(9) -0.71924(8) 0.0279(3) Uani 1 d . . .
H2A H 0.2970 -0.0517 -0.7645 0.033 Uiso 1 calc . . R
C7 C -0.2845(2) 0.00075(9) -0.94312(8) 0.0274(3) Uani 1 d . . .
H7A H -0.4278 -0.0220 -0.9370 0.033 Uiso 1 calc . . R
H7B H -0.2467 -0.0016 -0.9994 0.033 Uiso 1 calc . . R
C9 C -0.0944(2) 0.00253(9) -0.81991(8) 0.0231(3) Uani 1 d . . .
C3 C 0.2388(2) 0.05719(9) -0.69146(8) 0.0277(3) Uani 1 d . . .
H3A H 0.1987 0.0981 -0.7341 0.033 Uiso 1 calc . . R
H3B H 0.1482 0.0695 -0.6458 0.033 Uiso 1 calc . . R
C14 C 0.0778(2) -0.07555(9) -0.93814(8) 0.0277(3) Uani 1 d . . .
H14A H 0.0489 -0.1148 -0.9825 0.042 Uiso 1 calc . . GR
H14B H 0.1767 -0.1041 -0.9026 0.042 Uiso 1 calc . . GR
H14C H 0.1372 -0.0201 -0.9575 0.042 Uiso 1 calc . . GR
C15 C -0.2153(2) -0.14061(9) -0.85201(8) 0.0250(3) Uani 1 d . . .
H15 H -0.3615 -0.1291 -0.8350 0.030 Uiso 1 calc . . R
C1 C -0.0279(2) -0.05347(9) -0.74825(8) 0.0258(3) Uani 1 d . . .
H1A H -0.1237 -0.0396 -0.7037 0.031 Uiso 1 calc . . R
C10 C -0.0754(3) -0.15135(9) -0.77733(9) 0.0301(3) Uani 1 d . . .
H10A H 0.0550 -0.1826 -0.7905 0.036 Uiso 1 calc . . R
H10B H -0.1494 -0.1851 -0.7362 0.036 Uiso 1 calc . . R
C12 C -0.4895(3) 0.14119(9) -0.90282(9) 0.0356(4) Uani 1 d . . .
H12A H -0.5550 0.1454 -0.9545 0.053 Uiso 1 calc . . GR
H12B H -0.4769 0.2004 -0.8801 0.053 Uiso 1 calc . . GR
H12C H -0.5748 0.1041 -0.8685 0.053 Uiso 1 calc . . GR
C5 C -0.1678(2) 0.08549(9) -0.83006(8) 0.0262(3) Uani 1 d . . .
H5 H -0.1582 0.1304 -0.7914 0.031 Uiso 1 calc . . R
C4 C 0.4659(2) 0.07481(9) -0.66844(8) 0.0293(3) Uani 1 d . . .
H4A H 0.4991 0.0430 -0.6193 0.035 Uiso 1 calc . . R
H4B H 0.5595 0.0528 -0.7101 0.035 Uiso 1 calc . . R
C6 C -0.2689(2) 0.09933(9) -0.91136(8) 0.0262(3) Uani 1 d . . .
C8 C -0.1286(2) -0.05582(9) -0.89315(8) 0.0231(3) Uani 1 d . . .
C13 C -0.1332(3) 0.15939(10) -0.96556(9) 0.0368(4) Uani 1 d . . .
H13A H 0.0031 0.1319 -0.9733 0.055 Uiso 1 calc . . GR
H13B H -0.1155 0.2174 -0.9410 0.055 Uiso 1 calc . . GR
H13C H -0.2021 0.1665 -1.0164 0.055 Uiso 1 calc . . GR
C11 C 0.2549(3) -0.10715(11) -0.65299(11) 0.0528(5) Uani 1 d . . .
H11A H 0.4013 -0.1009 -0.6382 0.079 Uiso 1 calc . . GR
H11B H 0.2296 -0.1673 -0.6718 0.079 Uiso 1 calc . . GR
H11C H 0.1671 -0.0955 -0.6072 0.079 Uiso 1 calc . . GR


_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
O2 C15 1.4323(16) . ?
O1 C4 1.4318(16) . ?
C2 C3 1.5310(19) . ?
C2 C1 1.542(2) . ?
C2 C11 1.527(2) . ?
C7 C6 1.5586(18) . ?
C7 C8 1.5390(19) . ?
C9 C1 1.5166(18) . ?
C9 C5 1.3256(19) . ?
C9 C8 1.5144(18) . ?
C3 C4 1.506(2) . ?
C14 C8 1.5317(19) . ?
C15 C10 1.5367(19) . ?
C15 C8 1.5342(18) . ?
C1 C10 1.5600(18) . ?
C12 C6 1.530(2) . ?
C5 C6 1.5147(19) . ?
C6 C13 1.532(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
C3 C2 C1 111.13(11) . . ?
C11 C2 C3 111.20(12) . . ?
C11 C2 C1 110.37(13) . . ?
C8 C7 C6 106.64(10) . . ?
C5 C9 C1 134.92(13) . . ?
C5 C9 C8 112.17(11) . . ?
C8 C9 C1 111.37(11) . . ?
C4 C3 C2 112.63(12) . . ?
O2 C15 C10 113.35(11) . . ?
O2 C15 C8 112.78(10) . . ?
C8 C15 C10 104.12(11) . . ?
C2 C1 C10 113.58(12) . . ?
C9 C1 C2 115.89(11) . . ?
C9 C1 C10 102.16(11) . . ?
C15 C10 C1 105.48(10) . . ?
C9 C5 C6 112.80(12) . . ?
O1 C4 C3 109.83(11) . . ?
C12 C6 C7 110.80(12) . . ?
C12 C6 C13 109.11(12) . . ?
C5 C6 C7 101.82(10) . . ?
C5 C6 C12 110.74(12) . . ?
C5 C6 C13 111.93(12) . . ?
C13 C6 C7 112.31(11) . . ?
C9 C8 C7 102.58(10) . . ?
C9 C8 C14 112.62(11) . . ?
C9 C8 C15 99.05(10) . . ?
C14 C8 C7 112.41(11) . . ?
C14 C8 C15 111.49(11) . . ?
C15 C8 C7 117.53(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_12-hydroxydehydrobotrydienol
_database_code_depnum_ccdc_archive 'CCDC 1060374'
_audit_update_record             
;
2015-04-18 deposited with the CCDC.
2015-05-14 downloaded from the CCDC.
;
_audit_creation_date             2015-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            12-hydroxydehydrobotrydienol
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H22 O3'
_chemical_formula_sum            'C15 H22 O3'
_chemical_formula_weight         250.33
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.13361(13)
_cell_length_b                   10.68806(14)
_cell_length_c                   13.75024(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1342.31(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9548
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      62.8610
_cell_measurement_theta_min      4.8610
_exptl_absorpt_coefficient_mu    0.678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21683
_diffrn_reflns_theta_full        62.73
_diffrn_reflns_theta_max         62.73
_diffrn_reflns_theta_min         5.24
_diffrn_ambient_temperature      173.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0288
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -109.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184 -178.0000   90.0000 52

#__ type_ start__ end____ width___ exp.time_
  2 omega  -40.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184    0.0000   90.0000 146

#__ type_ start__ end____ width___ exp.time_
  3 omega   19.00   83.00   1.0000    1.0350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000  -60.0000 64

#__ type_ start__ end____ width___ exp.time_
  4 omega   61.00  163.00   1.0000    1.0350
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000   30.0000 102

#__ type_ start__ end____ width___ exp.time_
  5 omega   18.00   90.00   1.0000    1.0350
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000 -150.0000 72

#__ type_ start__ end____ width___ exp.time_
  6 omega   18.00   69.00   1.0000    1.0350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000   60.0000 51

#__ type_ start__ end____ width___ exp.time_
  7 omega   79.00  163.00   1.0000    1.0350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
  8 omega   19.00   77.00   1.0000    1.0350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000   90.0000 58

#__ type_ start__ end____ width___ exp.time_
  9 omega   18.00   69.00   1.0000    1.0350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000 -150.0000 51

#__ type_ start__ end____ width___ exp.time_
 10 omega   20.00   83.00   1.0000    1.0350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -50.0000 -105.0000 63

#__ type_ start__ end____ width___ exp.time_
 11 omega   35.00  134.00   1.0000    1.0350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  178.0000 -120.0000 99

#__ type_ start__ end____ width___ exp.time_
 12 omega   19.00   77.00   1.0000    1.0350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  150.0000 58

#__ type_ start__ end____ width___ exp.time_
 13 omega   60.00  161.00   1.0000    1.0350
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000 -180.0000 101

#__ type_ start__ end____ width___ exp.time_
 14 omega   19.00   83.00   1.0000    1.0350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000  -90.0000 64

#__ type_ start__ end____ width___ exp.time_
 15 omega   18.00   69.00   1.0000    1.0350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000   90.0000 51

#__ type_ start__ end____ width___ exp.time_
 16 omega   19.00   77.00   1.0000    1.0350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000 -180.0000 58

#__ type_ start__ end____ width___ exp.time_
 17 omega   19.00   77.00   1.0000    1.0350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
 18 omega   18.00   90.00   1.0000    1.0350
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000  -90.0000 72

#__ type_ start__ end____ width___ exp.time_
 19 omega   22.00   96.00   1.0000    1.0350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -57.0000   -8.7169 74

#__ type_ start__ end____ width___ exp.time_
 20 omega   69.00  159.00   1.0000    1.0350
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
 21 omega   19.00   77.00   1.0000    1.0350
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000   30.0000 58

#__ type_ start__ end____ width___ exp.time_
 22 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000  150.0000 89

#__ type_ start__ end____ width___ exp.time_
 23 omega   25.00   51.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega  108.00  144.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000   60.0000 36

#__ type_ start__ end____ width___ exp.time_
 25 omega -109.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.3684 -178.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
 26 omega -109.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.3684 -178.0000  -60.0000 52

#__ type_ start__ end____ width___ exp.time_
 27 omega    3.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.3684   77.0000 -120.0000 101

#__ type_ start__ end____ width___ exp.time_
 28 omega   60.00  161.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000   60.0000 101

#__ type_ start__ end____ width___ exp.time_
 29 omega   60.00  161.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000   90.0000 101

#__ type_ start__ end____ width___ exp.time_
 30 omega   18.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000   30.0000 72

#__ type_ start__ end____ width___ exp.time_
 31 omega   67.00  162.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000  -90.0000 95

#__ type_ start__ end____ width___ exp.time_
 32 omega   60.00  161.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000 -150.0000 101

#__ type_ start__ end____ width___ exp.time_
 33 omega   60.00  161.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  -90.0000 101

#__ type_ start__ end____ width___ exp.time_
 34 omega   60.00  161.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000   30.0000 101

#__ type_ start__ end____ width___ exp.time_
 35 omega   60.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 36 omega   60.00  161.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  -60.0000 101

#__ type_ start__ end____ width___ exp.time_
 37 omega   60.00  161.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000    0.0000 101

#__ type_ start__ end____ width___ exp.time_
 38 omega   19.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000  -13.8993 110

#__ type_ start__ end____ width___ exp.time_
 39 omega   60.00  161.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  120.0000 101

#__ type_ start__ end____ width___ exp.time_
 40 omega   60.00  161.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  150.0000 101

#__ type_ start__ end____ width___ exp.time_
 41 omega   69.00  159.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  120.0000 90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0873364000
_diffrn_orient_matrix_UB_12      -0.0562663000
_diffrn_orient_matrix_UB_13      0.0853147000
_diffrn_orient_matrix_UB_21      0.0543497000
_diffrn_orient_matrix_UB_22      -0.1316730000
_diffrn_orient_matrix_UB_23      -0.0279120000
_diffrn_orient_matrix_UB_31      0.1335754000
_diffrn_orient_matrix_UB_32      0.0167330000
_diffrn_orient_matrix_UB_33      0.0670943000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2078
_reflns_number_total             2146
_reflns_odcompleteness_completeness 97.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     63.60
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(19)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0290
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0440P)²+0.1652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0738
_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. 
;
_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.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C10(H10A,H10B), C12(H12A,H12B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
_atom_site_refinement_flags_posn
O1 O 0.14132(11) 0.40367(9) 0.42292(8) 0.0316(2) Uani 1 d . . .
H1 H 0.0720 0.3704 0.3952 0.047 Uiso 1 calc . . GR
O2 O -0.21263(13) 0.28903(9) 0.49298(8) 0.0372(3) Uani 1 d . . .
H2 H -0.2549 0.2365 0.5262 0.056 Uiso 1 calc . . GR
O3 O 0.04958(11) 0.73959(11) 0.16156(8) 0.0368(3) Uani 1 d . . .
H3 H 0.1099 0.7512 0.1183 0.055 Uiso 1 calc . . GR
C1 C -0.24654(16) 0.49917(12) 0.43336(10) 0.0220(3) Uani 1 d . . .
C15 C 0.09043(16) 0.46609(13) 0.50833(10) 0.0269(3) Uani 1 d . . .
H15A H 0.1733 0.4827 0.5505 0.032 Uiso 1 calc . . R
H15B H 0.0241 0.4110 0.5430 0.032 Uiso 1 calc . . R
C5 C -0.11120(14) 0.65372(11) 0.33997(9) 0.0202(3) Uani 1 d . . .
C6 C 0.03058(15) 0.72809(12) 0.33858(10) 0.0233(3) Uani 1 d . . .
C9 C -0.12225(14) 0.57480(11) 0.42064(9) 0.0198(3) Uani 1 d . . .
C2 C -0.35976(16) 0.50451(13) 0.36419(10) 0.0259(3) Uani 1 d . . .
C3 C -0.34733(15) 0.58752(14) 0.28622(10) 0.0271(3) Uani 1 d . . .
H3A H -0.4234 0.5929 0.2415 0.033 Uiso 1 calc . . R
C10 C -0.26358(16) 0.41176(12) 0.51899(10) 0.0254(3) Uani 1 d . . .
H10A H -0.2076 0.4431 0.5738 0.031 Uiso 1 calc . . R
H10B H -0.3657 0.4077 0.5381 0.031 Uiso 1 calc . . R
C12 C 0.12292(16) 0.70238(14) 0.24835(10) 0.0286(3) Uani 1 d . . .
H12A H 0.2148 0.7473 0.2535 0.034 Uiso 1 calc . . R
H12B H 0.1450 0.6137 0.2450 0.034 Uiso 1 calc . . R
C7 C 0.11389(15) 0.67744(13) 0.42811(10) 0.0274(3) Uani 1 d . . .
H7A H 0.1455 0.7465 0.4688 0.033 Uiso 1 calc . . R
H7B H 0.2000 0.6317 0.4071 0.033 Uiso 1 calc . . R
C4 C -0.22499(15) 0.66194(13) 0.27378(10) 0.0246(3) Uani 1 d . . .
H4 H -0.2192 0.7169 0.2215 0.029 Uiso 1 calc . . R
C14 C -0.02759(17) 0.65165(14) 0.58475(11) 0.0305(3) Uani 1 d . . .
H14A H -0.0979 0.6009 0.6185 0.046 Uiso 1 calc . . GR
H14B H -0.0684 0.7331 0.5731 0.046 Uiso 1 calc . . GR
H14C H 0.0592 0.6596 0.6237 0.046 Uiso 1 calc . . GR
C8 C 0.01150(14) 0.58965(12) 0.48692(10) 0.0223(3) Uani 1 d . . .
C11 C -0.49581(18) 0.42526(17) 0.37257(13) 0.0413(4) Uani 1 d . . .
H11A H -0.4687 0.3386 0.3766 0.062 Uiso 1 calc . . GR
H11B H -0.5564 0.4381 0.3164 0.062 Uiso 1 calc . . GR
H11C H -0.5489 0.4486 0.4300 0.062 Uiso 1 calc . . GR
C13 C -0.00204(19) 0.86908(13) 0.34628(12) 0.0351(4) Uani 1 d . . .
H13A H -0.0636 0.8941 0.2931 0.053 Uiso 1 calc . . GR
H13B H 0.0881 0.9151 0.3439 0.053 Uiso 1 calc . . GR
H13C H -0.0510 0.8859 0.4066 0.053 Uiso 1 calc . . GR


_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 C15 1.4284(18) . ?
O2 C10 1.4371(16) . ?
O3 C12 1.4251(18) . ?
C1 C9 1.4046(19) . ?
C1 C2 1.406(2) . ?
C1 C10 1.5111(19) . ?
C15 C8 1.5331(19) . ?
C5 C6 1.5196(18) . ?
C5 C9 1.3971(18) . ?
C5 C4 1.3843(19) . ?
C6 C12 1.525(2) . ?
C6 C7 1.5451(19) . ?
C6 C13 1.5397(19) . ?
C9 C8 1.5324(18) . ?
C2 C3 1.396(2) . ?
C2 C11 1.508(2) . ?
C3 C4 1.382(2) . ?
C7 C8 1.5521(19) . ?
C14 C8 1.5415(19) . ?

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
C9 C1 C2 119.13(12) . . ?
C9 C1 C10 122.42(12) . . ?
C2 C1 C10 118.45(12) . . ?
O1 C15 C8 113.42(11) . . ?
C9 C5 C6 112.79(11) . . ?
C4 C5 C6 126.75(12) . . ?
C4 C5 C9 120.40(12) . . ?
C5 C6 C12 112.78(11) . . ?
C5 C6 C7 103.08(10) . . ?
C5 C6 C13 110.26(12) . . ?
C12 C6 C7 108.22(11) . . ?
C12 C6 C13 109.83(12) . . ?
C13 C6 C7 112.55(12) . . ?
C1 C9 C8 129.04(12) . . ?
C5 C9 C1 120.31(12) . . ?
C5 C9 C8 110.61(11) . . ?
C1 C2 C11 122.10(13) . . ?
C3 C2 C1 119.04(13) . . ?
C3 C2 C11 118.85(13) . . ?
C4 C3 C2 121.76(13) . . ?
O2 C10 C1 109.70(11) . . ?
O3 C12 C6 111.78(11) . . ?
C6 C7 C8 109.28(10) . . ?
C3 C4 C5 119.28(12) . . ?
C15 C8 C7 109.72(11) . . ?
C15 C8 C14 108.16(11) . . ?
C9 C8 C15 113.57(11) . . ?
C9 C8 C7 103.48(10) . . ?
C9 C8 C14 112.27(11) . . ?
C14 C8 C7 109.53(11) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dehydrobotrydienol
_database_code_depnum_ccdc_archive 'CCDC 1060375'
_audit_update_record             
;
2015-04-18 deposited with the CCDC.
2015-05-14 downloaded from the CCDC.
;
_audit_creation_date             2015-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            dehydrobotrydienol
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H22 O2'
_chemical_formula_sum            'C15 H22 O2'
_chemical_formula_weight         234.33
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.8587(3)
_cell_length_b                   10.9481(4)
_cell_length_c                   13.7817(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1336.63(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4035
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      62.6810
_cell_measurement_theta_min      3.2270
_exptl_absorpt_coefficient_mu    0.590
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0850
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12262
_diffrn_reflns_theta_full        62.86
_diffrn_reflns_theta_max         62.86
_diffrn_reflns_theta_min         5.16
_diffrn_ambient_temperature      173.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0288
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -109.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184 -178.0000   30.0000 52

#__ type_ start__ end____ width___ exp.time_
  2 omega    8.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   38.0000 -180.0000 98

#__ type_ start__ end____ width___ exp.time_
  3 omega    8.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   38.0000  -90.0000 98

#__ type_ start__ end____ width___ exp.time_
  4 omega   18.00   69.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000 -150.0000 51

#__ type_ start__ end____ width___ exp.time_
  5 omega   61.00  163.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000   60.0000 102

#__ type_ start__ end____ width___ exp.time_
  6 omega   19.00   77.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000 -180.0000 58

#__ type_ start__ end____ width___ exp.time_
  7 omega   19.00   77.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
  8 omega   19.00   83.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000   30.0000 64

#__ type_ start__ end____ width___ exp.time_
  9 omega   18.00   90.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000  -30.0000 72

#__ type_ start__ end____ width___ exp.time_
 10 omega   19.00   83.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000 -180.0000 64

#__ type_ start__ end____ width___ exp.time_
 11 omega   18.00   90.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000 -120.0000 72

#__ type_ start__ end____ width___ exp.time_
 12 omega   19.00   77.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  -90.0000 58

#__ type_ start__ end____ width___ exp.time_
 13 omega   19.00   83.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000  150.0000 64

#__ type_ start__ end____ width___ exp.time_
 14 omega   18.00   90.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000  150.0000 72

#__ type_ start__ end____ width___ exp.time_
 15 omega   19.00   83.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000    0.0000 64

#__ type_ start__ end____ width___ exp.time_
 16 omega   18.00   69.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000  -60.0000 51

#__ type_ start__ end____ width___ exp.time_
 17 omega -109.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184 -178.0000  -90.0000 52

#__ type_ start__ end____ width___ exp.time_
 18 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000    0.0000 89

#__ type_ start__ end____ width___ exp.time_
 19 omega  -36.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184  -57.0000 -150.0000 91

#__ type_ start__ end____ width___ exp.time_
 20 omega   69.00  159.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
 21 omega   37.00  164.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000   15.0000 -150.0000 127

#__ type_ start__ end____ width___ exp.time_
 22 omega   60.00  123.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000   90.0000 63

#__ type_ start__ end____ width___ exp.time_
 23 omega   61.00  163.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000  -60.0000 102

#__ type_ start__ end____ width___ exp.time_
 24 omega  137.00  162.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 25 omega   86.00  112.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega -110.00  -53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.3684  178.0000 -120.0000 57

#__ type_ start__ end____ width___ exp.time_
 27 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.3684   57.0000  -60.0000 89

#__ type_ start__ end____ width___ exp.time_
 28 omega    3.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.3684   77.0000 -180.0000 101

#__ type_ start__ end____ width___ exp.time_
 29 omega    3.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.3684   77.0000   60.0000 101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0715824000
_diffrn_orient_matrix_UB_12      -0.1218380000
_diffrn_orient_matrix_UB_13      0.0316859000
_diffrn_orient_matrix_UB_21      -0.1556357000
_diffrn_orient_matrix_UB_22      -0.0623860000
_diffrn_orient_matrix_UB_23      -0.0062314000
_diffrn_orient_matrix_UB_31      0.0300829000
_diffrn_orient_matrix_UB_32      -0.0327122000
_diffrn_orient_matrix_UB_33      -0.1069838000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1869
_reflns_number_total             2141
_reflns_odcompleteness_completeness 97.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     63.60
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(7)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0730
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1022P)²+1.5243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1899
_refine_ls_wR_factor_ref         0.2014
_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. 
;
_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.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C15(H15A,H15B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
_atom_site_refinement_flags_posn
O1 O 0.2029(3) 0.3010(2) -0.0043(2) 0.0446(7) Uani 1 d . . .
H1 H 0.1146 0.3037 0.0134 0.067 Uiso 1 calc . . GR
C10 C 0.2566(4) 0.4219(3) -0.0212(3) 0.0357(9) Uani 1 d . . .
H10A H 0.2009 0.4572 -0.0750 0.043 Uiso 1 calc . . R
H10B H 0.3621 0.4180 -0.0399 0.043 Uiso 1 calc . . R
C3 C 0.3448(5) 0.5847(4) 0.2140(3) 0.0409(10) Uani 1 d . . .
H3 H 0.4239 0.5895 0.2582 0.049 Uiso 1 calc . . R
C9 C 0.1122(4) 0.5747(3) 0.0811(3) 0.0290(8) Uani 1 d . . .
C1 C 0.2413(4) 0.5036(3) 0.0655(2) 0.0289(8) Uani 1 d . . .
O2 O -0.0922(4) 0.3719(3) 0.0506(3) 0.0622(10) Uani 1 d . . .
H2 H -0.1514 0.3176 0.0354 0.093 Uiso 1 calc . . GR
C5 C 0.1003(5) 0.6481(3) 0.1630(3) 0.0342(9) Uani 1 d . . .
C8 C -0.0308(4) 0.5862(3) 0.0183(3) 0.0332(8) Uani 1 d . . .
C2 C 0.3576(4) 0.5071(3) 0.1355(3) 0.0351(9) Uani 1 d . . .
C4 C 0.2179(5) 0.6556(4) 0.2287(3) 0.0397(10) Uani 1 d . . .
H4 H 0.2116 0.7074 0.2820 0.048 Uiso 1 calc . . R
C15 C -0.1009(5) 0.4653(4) -0.0158(4) 0.0586(13) Uani 1 d . . .
H15A H -0.2063 0.4794 -0.0313 0.070 Uiso 1 calc . . R
H15B H -0.0507 0.4398 -0.0750 0.070 Uiso 1 calc . . R
C11 C 0.4963(5) 0.4267(5) 0.1259(4) 0.0513(11) Uani 1 d . . .
H11A H 0.5525 0.4505 0.0694 0.077 Uiso 1 calc . . GR
H11B H 0.4658 0.3430 0.1198 0.077 Uiso 1 calc . . GR
H11C H 0.5585 0.4360 0.1825 0.077 Uiso 1 calc . . GR
C14 C -0.0039(6) 0.6582(5) -0.0744(3) 0.0595(13) Uani 1 d . . .
H14A H 0.0265 0.7399 -0.0583 0.089 Uiso 1 calc . . GR
H14B H -0.0954 0.6608 -0.1117 0.089 Uiso 1 calc . . GR
H14C H 0.0740 0.6194 -0.1117 0.089 Uiso 1 calc . . GR
C6 C -0.0498(5) 0.7145(4) 0.1693(3) 0.0473(11) Uani 1 d . . .
C12 C -0.1286(7) 0.6927(5) 0.2649(4) 0.0723(16) Uani 1 d . . .
H12A H -0.1424 0.6066 0.2745 0.108 Uiso 1 calc . . GR
H12B H -0.2252 0.7325 0.2644 0.108 Uiso 1 calc . . GR
H12C H -0.0683 0.7252 0.3167 0.108 Uiso 1 calc . . GR
C13 C -0.0270(7) 0.8514(4) 0.1566(5) 0.0828(19) Uani 1 d . . .
H13A H 0.0405 0.8810 0.2058 0.124 Uiso 1 calc . . GR
H13B H -0.1224 0.8924 0.1623 0.124 Uiso 1 calc . . GR
H13C H 0.0153 0.8673 0.0937 0.124 Uiso 1 calc . . GR
C7 C -0.1410(6) 0.6508(6) 0.0865(4) 0.0688(15) Uani 1 d . . .
H7A H -0.2108 0.5919 0.1141 0.083 Uiso 1 calc . . R
H7B H -0.1989 0.7111 0.0508 0.083 Uiso 1 calc . . R


_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 C10 1.426(5) . ?
C10 C1 1.499(5) . ?
C3 C2 1.381(6) . ?
C3 C4 1.381(6) . ?
C9 C1 1.400(5) . ?
C9 C5 1.390(5) . ?
C9 C8 1.539(5) . ?
C1 C2 1.412(5) . ?
O2 C15 1.374(5) . ?
C5 C4 1.383(6) . ?
C5 C6 1.517(6) . ?
C8 C15 1.536(6) . ?
C8 C14 1.519(6) . ?
C8 C7 1.528(6) . ?
C2 C11 1.517(6) . ?
C6 C12 1.511(7) . ?
C6 C13 1.523(6) . ?
C6 C7 1.562(7) . ?

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
O1 C10 C1 113.2(3) . . ?
C4 C3 C2 121.8(4) . . ?
C1 C9 C8 129.2(3) . . ?
C5 C9 C1 120.5(3) . . ?
C5 C9 C8 110.3(3) . . ?
C9 C1 C10 121.9(3) . . ?
C9 C1 C2 118.5(3) . . ?
C2 C1 C10 119.6(3) . . ?
C9 C5 C6 112.9(3) . . ?
C4 C5 C9 120.6(4) . . ?
C4 C5 C6 126.5(3) . . ?
C15 C8 C9 115.7(3) . . ?
C14 C8 C9 112.7(3) . . ?
C14 C8 C15 104.7(4) . . ?
C14 C8 C7 112.2(4) . . ?
C7 C8 C9 102.6(3) . . ?
C7 C8 C15 109.2(4) . . ?
C3 C2 C1 119.5(4) . . ?
C3 C2 C11 119.4(4) . . ?
C1 C2 C11 121.1(4) . . ?
C3 C4 C5 119.0(3) . . ?
O2 C15 C8 114.5(4) . . ?
C5 C6 C13 110.4(4) . . ?
C5 C6 C7 101.4(3) . . ?
C12 C6 C5 112.3(4) . . ?
C12 C6 C13 108.5(4) . . ?
C12 C6 C7 109.1(5) . . ?
C13 C6 C7 115.1(5) . . ?
C8 C7 C6 108.9(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
