# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_C5
_database_code_depnum_ccdc_archive 'CCDC 1590402'
_audit_update_record             
;
2018-09-24 deposited with the CCDC.
2018-11-05 downloaded from the CCDC.
;

_audit_creation_date             2018-09-06T11:38:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C6  H12  O2'
_chemical_formula_sum            'C6 H12 O2'
_chemical_formula_weight         116.16

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.309(11)
_cell_length_b                   16.54(2)
_cell_length_c                   6.169(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.823(15)
_cell_angle_gamma                90
_cell_volume                     705.9(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    159(2)
_cell_measurement_reflns_used    1467
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      26.06
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_diffrn    1.093
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS
        (Sheldrick, 1996)
;

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

_exptl_absorpt_coefficient_mu    0.08
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.6072
_exptl_absorpt_correction_T_max  0.7457
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.976

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

_diffrn_ambient_temperature      159(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0944
_diffrn_reflns_av_unetI/netI     0.0795
_diffrn_reflns_number            5847
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.192
_diffrn_reflns_theta_max         25.972
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.701
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.701
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.701
_reflns_Friedel_coverage         0
_reflns_number_total             1400
_reflns_number_gt                850
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'Ortep for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0726P)²+1.4143P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1400
_refine_ls_number_parameters     74
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1615
_refine_ls_R_factor_gt           0.1024
_refine_ls_wR_factor_ref         0.2717
_refine_ls_wR_factor_gt          0.2479
_refine_ls_goodness_of_fit_ref   1.232
_refine_ls_restrained_S_all      1.232
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.118

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2539(6) 0.5821(3) 0.5907(7) 0.0282(10) Uani 1 1 d . . . . .
C2 C 0.2682(7) 0.4932(3) 0.6418(7) 0.0318(11) Uani 1 1 d . . . . .
H2A H 0.399153 0.474706 0.650103 0.038 Uiso 1 1 calc R U . . .
H2B H 0.174535 0.464622 0.511945 0.038 Uiso 1 1 calc R U . . .
C3 C 0.2316(7) 0.4679(3) 0.8608(8) 0.0312(11) Uani 1 1 d . . . . .
H3A H 0.319643 0.498286 0.991364 0.037 Uiso 1 1 calc R U . . .
H3B H 0.097201 0.481982 0.849626 0.037 Uiso 1 1 calc R U . . .
C4 C 0.2623(8) 0.3789(3) 0.9050(8) 0.0390(13) Uani 1 1 d . . . . .
H4A H 0.39683 0.365401 0.915286 0.047 Uiso 1 1 calc R U . . .
H4B H 0.175143 0.349083 0.772654 0.047 Uiso 1 1 calc R U . . .
C5 C 0.2268(8) 0.3496(3) 1.1221(9) 0.0500(14) Uani 1 1 d . . . . .
H5A H 0.249715 0.291204 1.138721 0.075 Uiso 1 1 calc R U . . .
H5B H 0.314893 0.377549 1.255083 0.075 Uiso 1 1 calc R U . . .
H5C H 0.092841 0.361205 1.112217 0.075 Uiso 1 1 calc R U . . .
C6 C 0.2765(8) 0.6807(3) 0.3221(8) 0.0427(13) Uani 1 1 d . . . . .
H6A H 0.299567 0.684115 0.174451 0.064 Uiso 1 1 calc R U . . .
H6B H 0.149167 0.703411 0.307146 0.064 Uiso 1 1 calc R U . . .
H6C H 0.376444 0.711268 0.437445 0.064 Uiso 1 1 calc R U . . .
O1 O 0.2828(5) 0.59667(18) 0.3921(5) 0.0390(9) Uani 1 1 d . . . . .
O2 O 0.2227(6) 0.63341(18) 0.7097(6) 0.0485(11) Uani 1 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 O2 1.191(5) . ?
C1 O1 1.330(5) . ?
C1 C2 1.501(6) . ?
C2 C3 1.518(6) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C4 1.502(6) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 C5 1.523(7) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 O1 1.452(6) . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?

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
O2 C1 O1 123.9(4) . . ?
O2 C1 C2 125.6(4) . . ?
O1 C1 C2 110.5(3) . . ?
C1 C2 C3 115.9(3) . . ?
C1 C2 H2A 108.3 . . ?
C3 C2 H2A 108.3 . . ?
C1 C2 H2B 108.3 . . ?
C3 C2 H2B 108.3 . . ?
H2A C2 H2B 107.4 . . ?
C4 C3 C2 111.9(4) . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C3 C4 C5 114.4(4) . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O1 C6 H6A 109.5 . . ?
O1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 O1 C6 116.6(3) . . ?

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 C1 C2 C3 2.5(7) . . . . ?
O1 C1 C2 C3 -178.1(4) . . . . ?
C1 C2 C3 C4 -176.2(4) . . . . ?
C2 C3 C4 C5 -179.7(4) . . . . ?
O2 C1 O1 C6 0.5(7) . . . . ?
C2 C1 O1 C6 -179.0(4) . . . . ?

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
_geom_hbond_publ_flag
C2 H2A O1 0.99 2.69 3.669(7) 169 3_666 yes

####################################################################### 
# 
# 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_C11
_database_code_depnum_ccdc_archive 'CCDC 1590408'
_audit_update_record             
;
2018-09-24 deposited with the CCDC.
2018-11-05 downloaded from the CCDC.
;

_audit_creation_date             2018-09-10T14:45:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C12  H24  O2'
_chemical_formula_sum            'C12 H24 O2'
_chemical_formula_weight         200.31

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.5680(16)
_cell_length_b                   7.214(2)
_cell_length_c                   31.782(9)
_cell_angle_alpha                89.956(6)
_cell_angle_beta                 85.324(4)
_cell_angle_gamma                89.866(4)
_cell_volume                     1272.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5540
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      28.31
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_diffrn    1.046
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS
        (Sheldrick, 1996)
;

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

_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.98
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.98

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_number            14693
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         3.102
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_reflns_Friedel_coverage         0
_reflns_number_total             4662
_reflns_number_gt                3454
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2016)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'Ortep for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0615P)²+0.7581P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4662
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.159
_refine_ls_wR_factor_gt          0.1456
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.22
_refine_diff_density_rms         0.041

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1827(4) 0.2994(4) 0.38660(7) 0.0291(5) Uani 1 1 d . . . . .
C2 C -0.1230(4) 0.3603(3) 0.34178(7) 0.0269(5) Uani 1 1 d . . . . .
H2A H -0.104119 0.496682 0.341503 0.032 Uiso 1 1 calc R U . . .
H2B H -0.261642 0.330619 0.325374 0.032 Uiso 1 1 calc R U . . .
C3 C 0.1018(4) 0.2752(3) 0.31937(7) 0.0269(5) Uani 1 1 d . . . . .
H3A H 0.083296 0.138853 0.318161 0.032 Uiso 1 1 calc R U . . .
H3B H 0.242597 0.302633 0.335417 0.032 Uiso 1 1 calc R U . . .
C4 C 0.1453(4) 0.3523(3) 0.27455(7) 0.0262(5) Uani 1 1 d . . . . .
H4A H -0.001332 0.331476 0.259558 0.031 Uiso 1 1 calc R U . . .
H4B H 0.169395 0.487939 0.276338 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3603(4) 0.2684(3) 0.24839(7) 0.0266(5) Uani 1 1 d . . . . .
H5A H 0.33783 0.132698 0.246512 0.032 Uiso 1 1 calc R U . . .
H5B H 0.508259 0.290891 0.262889 0.032 Uiso 1 1 calc R U . . .
C6 C 0.3932(4) 0.3490(3) 0.20389(7) 0.0260(5) Uani 1 1 d . . . . .
H6A H 0.243979 0.327539 0.189681 0.031 Uiso 1 1 calc R U . . .
H6B H 0.415705 0.484663 0.205968 0.031 Uiso 1 1 calc R U . . .
C7 C 0.6056(4) 0.2676(4) 0.17663(7) 0.0276(5) Uani 1 1 d . . . . .
H7A H 0.755217 0.289734 0.19067 0.033 Uiso 1 1 calc R U . . .
H7B H 0.583712 0.131857 0.174568 0.033 Uiso 1 1 calc R U . . .
C8 C 0.6350(4) 0.3489(4) 0.13224(7) 0.0292(6) Uani 1 1 d . . . . .
H8A H 0.658475 0.484455 0.134319 0.035 Uiso 1 1 calc R U . . .
H8B H 0.484646 0.32795 0.118333 0.035 Uiso 1 1 calc R U . . .
C9 C 0.8456(4) 0.2665(4) 0.10471(7) 0.0305(6) Uani 1 1 d . . . . .
H9A H 0.995898 0.28688 0.118682 0.037 Uiso 1 1 calc R U . . .
H9B H 0.821743 0.131037 0.102501 0.037 Uiso 1 1 calc R U . . .
C10 C 0.8756(5) 0.3484(4) 0.06048(8) 0.0381(6) Uani 1 1 d . . . . .
H10A H 0.898447 0.484042 0.062653 0.046 Uiso 1 1 calc R U . . .
H10B H 0.72595 0.327175 0.046385 0.046 Uiso 1 1 calc R U . . .
C11 C 1.0874(5) 0.2665(5) 0.03331(8) 0.0510(8) Uani 1 1 d . . . . .
H11A H 1.098432 0.325567 0.005442 0.077 Uiso 1 1 calc R U . . .
H11B H 1.063355 0.132861 0.030131 0.077 Uiso 1 1 calc R U . . .
H11C H 1.236684 0.288303 0.046857 0.077 Uiso 1 1 calc R U . . .
C12 C -0.4851(5) 0.3172(5) 0.44347(8) 0.0523(8) Uani 1 1 d . . . . .
H12A H -0.656052 0.349435 0.448645 0.078 Uiso 1 1 calc R U . . .
H12B H -0.390504 0.391043 0.462002 0.078 Uiso 1 1 calc R U . . .
H12C H -0.462708 0.185172 0.449278 0.078 Uiso 1 1 calc R U . . .
C13 C 0.1640(5) 0.7891(4) 0.41325(7) 0.0310(6) Uani 1 1 d . . . . .
C14 C 0.3822(4) 0.8558(4) 0.38724(7) 0.0316(6) Uani 1 1 d . . . . .
H14A H 0.527411 0.821732 0.40156 0.038 Uiso 1 1 calc R U . . .
H14B H 0.376055 0.992725 0.385492 0.038 Uiso 1 1 calc R U . . .
C15 C 0.4057(4) 0.7764(4) 0.34260(7) 0.0287(5) Uani 1 1 d . . . . .
H15A H 0.423035 0.639993 0.34418 0.034 Uiso 1 1 calc R U . . .
H15B H 0.256561 0.803652 0.328765 0.034 Uiso 1 1 calc R U . . .
C16 C 0.6206(4) 0.8556(3) 0.31586(7) 0.0272(5) Uani 1 1 d . . . . .
H16A H 0.768746 0.831699 0.330234 0.033 Uiso 1 1 calc R U . . .
H16B H 0.600573 0.991633 0.313727 0.033 Uiso 1 1 calc R U . . .
C17 C 0.6517(4) 0.7742(4) 0.27150(7) 0.0270(5) Uani 1 1 d . . . . .
H17A H 0.670283 0.638061 0.273682 0.032 Uiso 1 1 calc R U . . .
H17B H 0.50375 0.798804 0.257109 0.032 Uiso 1 1 calc R U . . .
C18 C 0.8675(4) 0.8517(3) 0.24454(7) 0.0264(5) Uani 1 1 d . . . . .
H18A H 1.015204 0.827573 0.259036 0.032 Uiso 1 1 calc R U . . .
H18B H 0.84844 0.98772 0.242303 0.032 Uiso 1 1 calc R U . . .
C19 C 0.9004(4) 0.7702(4) 0.20019(7) 0.0276(5) Uani 1 1 d . . . . .
H19A H 0.922165 0.634411 0.202362 0.033 Uiso 1 1 calc R U . . .
H19B H 0.752032 0.792793 0.18577 0.033 Uiso 1 1 calc R U . . .
C20 C 1.1144(4) 0.8507(4) 0.17337(7) 0.0291(6) Uani 1 1 d . . . . .
H20A H 1.262636 0.826943 0.187742 0.035 Uiso 1 1 calc R U . . .
H20B H 1.093351 0.986761 0.171622 0.035 Uiso 1 1 calc R U . . .
C21 C 1.1488(4) 0.7728(4) 0.12870(7) 0.0303(6) Uani 1 1 d . . . . .
H21A H 1.171469 0.636862 0.130318 0.036 Uiso 1 1 calc R U . . .
H21B H 1.000753 0.796094 0.114238 0.036 Uiso 1 1 calc R U . . .
C22 C 1.3622(5) 0.8560(4) 0.10261(8) 0.0363(6) Uani 1 1 d . . . . .
H22A H 1.510488 0.830537 0.116833 0.044 Uiso 1 1 calc R U . . .
H22B H 1.340998 0.992188 0.101535 0.044 Uiso 1 1 calc R U . . .
C23 C 1.3952(6) 0.7818(5) 0.05768(9) 0.0539(8) Uani 1 1 d . . . . .
H23A H 1.529683 0.846139 0.042172 0.081 Uiso 1 1 calc R U . . .
H23B H 1.247359 0.802928 0.043587 0.081 Uiso 1 1 calc R U . . .
H23C H 1.429632 0.648624 0.058357 0.081 Uiso 1 1 calc R U . . .
C24 C -0.0363(5) 0.7759(5) 0.48134(8) 0.0513(8) Uani 1 1 d . . . . .
H24A H -0.010559 0.803519 0.510818 0.077 Uiso 1 1 calc R U . . .
H24B H -0.068046 0.643234 0.47836 0.077 Uiso 1 1 calc R U . . .
H24C H -0.174623 0.847292 0.472937 0.077 Uiso 1 1 calc R U . . .
O1 O -0.4058(3) 0.3556(3) 0.40002(5) 0.0395(5) Uani 1 1 d . . . . .
O2 O -0.0538(3) 0.2140(3) 0.40835(5) 0.0478(5) Uani 1 1 d . . . . .
O3 O 0.1763(3) 0.8258(3) 0.45464(5) 0.0403(5) Uani 1 1 d . . . . .
O4 O -0.0069(3) 0.7138(3) 0.40022(6) 0.0493(6) Uani 1 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 O2 1.205(3) . ?
C1 O1 1.342(3) . ?
C1 C2 1.502(3) . ?
C2 C3 1.517(3) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C4 1.530(3) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 C5 1.525(3) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 C6 1.526(3) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 C7 1.525(3) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 C8 1.524(3) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 C9 1.524(3) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C10 1.521(3) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C11 1.522(4) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 O1 1.442(3) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 O4 1.199(3) . ?
C13 O3 1.349(3) . ?
C13 C14 1.493(4) . ?
C14 C15 1.526(3) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C15 C16 1.522(3) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 C17 1.525(3) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 C18 1.525(3) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 C19 1.525(3) . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
C19 C20 1.523(3) . ?
C19 H19A 0.99 . ?
C19 H19B 0.99 . ?
C20 C21 1.525(3) . ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?
C21 C22 1.517(4) . ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?
C22 C23 1.522(4) . ?
C22 H22A 0.99 . ?
C22 H22B 0.99 . ?
C23 H23A 0.98 . ?
C23 H23B 0.98 . ?
C23 H23C 0.98 . ?
C24 O3 1.446(3) . ?
C24 H24A 0.98 . ?
C24 H24B 0.98 . ?
C24 H24C 0.98 . ?

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
O2 C1 O1 123.4(2) . . ?
O2 C1 C2 126.7(2) . . ?
O1 C1 C2 110.0(2) . . ?
C1 C2 C3 116.0(2) . . ?
C1 C2 H2A 108.3 . . ?
C3 C2 H2A 108.3 . . ?
C1 C2 H2B 108.3 . . ?
C3 C2 H2B 108.3 . . ?
H2A C2 H2B 107.4 . . ?
C2 C3 C4 110.62(19) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 114.92(19) . . ?
C5 C4 H4A 108.5 . . ?
C3 C4 H4A 108.5 . . ?
C5 C4 H4B 108.5 . . ?
C3 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
C4 C5 C6 112.61(19) . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C5 114.19(19) . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C8 C7 C6 113.49(19) . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 C9 113.7(2) . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C8 113.6(2) . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 C11 113.3(2) . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
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 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 C13 O3 122.1(2) . . ?
O4 C13 C14 126.1(2) . . ?
O3 C13 C14 111.8(2) . . ?
C13 C14 C15 113.4(2) . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C14 112.4(2) . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 C17 113.31(19) . . ?
C15 C16 H16A 108.9 . . ?
C17 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
C17 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C16 113.74(19) . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 C19 114.04(19) . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C19 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 C18 113.5(2) . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 C21 114.4(2) . . ?
C19 C20 H20A 108.7 . . ?
C21 C20 H20A 108.7 . . ?
C19 C20 H20B 108.7 . . ?
C21 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C22 C21 C20 113.3(2) . . ?
C22 C21 H21A 108.9 . . ?
C20 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
C20 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C21 C22 C23 113.7(2) . . ?
C21 C22 H22A 108.8 . . ?
C23 C22 H22A 108.8 . . ?
C21 C22 H22B 108.8 . . ?
C23 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 O1 C12 116.7(2) . . ?
C13 O3 C24 114.7(2) . . ?

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 C1 C2 C3 12.2(4) . . . . ?
O1 C1 C2 C3 -168.3(2) . . . . ?
C1 C2 C3 C4 -178.5(2) . . . . ?
C2 C3 C4 C5 -177.0(2) . . . . ?
C3 C4 C5 C6 179.4(2) . . . . ?
C4 C5 C6 C7 -179.6(2) . . . . ?
C5 C6 C7 C8 179.7(2) . . . . ?
C6 C7 C8 C9 -179.4(2) . . . . ?
C7 C8 C9 C10 -179.7(2) . . . . ?
C8 C9 C10 C11 179.6(2) . . . . ?
O4 C13 C14 C15 -15.3(4) . . . . ?
O3 C13 C14 C15 165.7(2) . . . . ?
C13 C14 C15 C16 176.4(2) . . . . ?
C14 C15 C16 C17 178.4(2) . . . . ?
C15 C16 C17 C18 -179.61(19) . . . . ?
C16 C17 C18 C19 179.75(19) . . . . ?
C17 C18 C19 C20 179.18(19) . . . . ?
C18 C19 C20 C21 -179.31(19) . . . . ?
C19 C20 C21 C22 179.7(2) . . . . ?
C20 C21 C22 C23 -178.9(2) . . . . ?
O2 C1 O1 C12 3.0(4) . . . . ?
C2 C1 O1 C12 -176.5(2) . . . . ?
O4 C13 O3 C24 -2.9(4) . . . . ?
C14 C13 O3 C24 176.1(2) . . . . ?

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
_geom_hbond_publ_flag
C2 H2A O4 0.99 2.53 3.254(3) 130 . yes
C14 H14A O4 0.99 2.7 3.606(3) 152 1_655 yes
C24 H24A O2 0.98 2.63 3.583(3) 166 2_566 yes

####################################################################### 
# 
# 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_C8
_database_code_depnum_ccdc_archive 'CCDC 1590405'
_audit_update_record             
;
2018-09-24 deposited with the CCDC.
2018-11-05 downloaded from the CCDC.
;

_audit_creation_date             2018-09-06T12:17:38-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C9  H18  O2'
_chemical_formula_sum            'C9 H18 O2'
_chemical_formula_weight         158.23

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_Int_Tables_number      60
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   50.25(3)
_cell_length_b                   7.055(4)
_cell_length_c                   5.609(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1988(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9582
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      28.35
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_diffrn    1.057
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS
        (Sheldrick, 1996)
;

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

_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.5892
_exptl_absorpt_correction_T_max  0.7457
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.979

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_number            18160
_diffrn_reflns_limit_h_min       -60
_diffrn_reflns_limit_h_max       60
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.916
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.984
_reflns_Friedel_coverage         0
_reflns_number_total             1824
_reflns_number_gt                1558
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2016)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'Ortep for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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)+(0.0493P)²+8.6090P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.021(4)
_refine_ls_number_reflns         1824
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0948
_refine_ls_wR_factor_ref         0.2505
_refine_ls_wR_factor_gt          0.2464
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.072

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.56568(7) 0.2612(5) 0.8602(7) 0.0238(9) Uani 1 1 d . . . . .
C2 C 0.58305(7) 0.2075(5) 0.6519(7) 0.0255(9) Uani 1 1 d . . . . .
H2A H 0.574552 0.253705 0.503647 0.031 Uiso 1 1 calc R U . . .
H2B H 0.58391 0.067499 0.642303 0.031 Uiso 1 1 calc R U . . .
C3 C 0.61152(7) 0.2854(5) 0.6632(7) 0.0241(9) Uani 1 1 d . . . . .
H3A H 0.61093 0.425386 0.65218 0.029 Uiso 1 1 calc R U . . .
H3B H 0.619471 0.251762 0.819046 0.029 Uiso 1 1 calc R U . . .
C4 C 0.62920(7) 0.2082(5) 0.4636(7) 0.0234(9) Uani 1 1 d . . . . .
H4A H 0.620666 0.235906 0.308331 0.028 Uiso 1 1 calc R U . . .
H4B H 0.630413 0.06877 0.479804 0.028 Uiso 1 1 calc R U . . .
C5 C 0.65748(7) 0.2912(5) 0.4625(7) 0.0241(9) Uani 1 1 d . . . . .
H5A H 0.656245 0.430158 0.440553 0.029 Uiso 1 1 calc R U . . .
H5B H 0.66572 0.267779 0.620065 0.029 Uiso 1 1 calc R U . . .
C6 C 0.67573(7) 0.2100(5) 0.2689(7) 0.0254(9) Uani 1 1 d . . . . .
H6A H 0.677282 0.071343 0.292662 0.031 Uiso 1 1 calc R U . . .
H6B H 0.667354 0.231204 0.111396 0.031 Uiso 1 1 calc R U . . .
C7 C 0.70368(8) 0.2962(6) 0.2664(7) 0.0301(10) Uani 1 1 d . . . . .
H7A H 0.702165 0.434474 0.239582 0.036 Uiso 1 1 calc R U . . .
H7B H 0.711959 0.27689 0.424664 0.036 Uiso 1 1 calc R U . . .
C8 C 0.72188(8) 0.2122(6) 0.0759(8) 0.0351(11) Uani 1 1 d . . . . .
H8A H 0.739366 0.273361 0.084043 0.053 Uiso 1 1 calc R U . . .
H8B H 0.723885 0.075701 0.103252 0.053 Uiso 1 1 calc R U . . .
H8C H 0.71408 0.233452 -0.082024 0.053 Uiso 1 1 calc R U . . .
C9 C 0.52228(9) 0.2544(8) 1.0249(9) 0.0486(13) Uani 1 1 d . . . . .
H9A H 0.503923 0.221883 0.982485 0.073 Uiso 1 1 calc R U . . .
H9B H 0.528074 0.175792 1.15923 0.073 Uiso 1 1 calc R U . . .
H9C H 0.523202 0.388475 1.070089 0.073 Uiso 1 1 calc R U . . .
O1 O 0.53961(5) 0.2205(5) 0.8209(5) 0.0389(9) Uani 1 1 d . . . . .
O2 O 0.57342(6) 0.3288(4) 1.0452(5) 0.0344(8) Uani 1 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 O2 1.206(5) . ?
C1 O1 1.359(5) . ?
C1 C2 1.507(5) . ?
C2 C3 1.534(5) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C4 1.529(5) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 C5 1.537(5) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 C6 1.532(5) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 C7 1.531(5) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 C8 1.526(5) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 O1 1.457(5) . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?

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
O2 C1 O1 122.3(3) . . ?
O2 C1 C2 125.4(3) . . ?
O1 C1 C2 112.3(3) . . ?
C1 C2 C3 114.7(3) . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
C3 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
C4 C3 C2 112.6(3) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C3 C4 C5 113.9(3) . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 114.4(3) . . ?
C6 C5 H5A 108.7 . . ?
C4 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C7 C6 C5 114.0(3) . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C8 C7 C6 113.7(3) . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 O1 C9 114.4(3) . . ?

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 C1 C2 C3 -13.4(6) . . . . ?
O1 C1 C2 C3 168.2(3) . . . . ?
C1 C2 C3 C4 173.3(3) . . . . ?
C2 C3 C4 C5 177.1(3) . . . . ?
C3 C4 C5 C6 177.9(3) . . . . ?
C4 C5 C6 C7 178.9(3) . . . . ?
C5 C6 C7 C8 179.0(3) . . . . ?
O2 C1 O1 C9 -3.5(6) . . . . ?
C2 C1 O1 C9 174.9(4) . . . . ?

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
_geom_hbond_publ_flag
C2 H2A O2 0.99 2.63 3.542(5) 154 1_554 yes
C3 H3A O2 0.99 2.63 3.393(5) 134 7_565 yes

####################################################################### 
# 
# 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_C9
_database_code_depnum_ccdc_archive 'CCDC 1590406'
_audit_update_record             
;
2018-09-24 deposited with the CCDC.
2018-11-05 downloaded from the CCDC.
;

_audit_creation_date             2018-09-06T14:04:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C10  H20  O2'
_chemical_formula_sum            'C10 H20 O2'
_chemical_formula_weight         172.26

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.565(3)
_cell_length_b                   7.183(4)
_cell_length_c                   27.043(14)
_cell_angle_alpha                90.145(7)
_cell_angle_beta                 91.445(7)
_cell_angle_gamma                90.099(7)
_cell_volume                     1080.7(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2624
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      25.13
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_diffrn    1.059
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS
        (Sheldrick, 1996)
;

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

_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.5433
_exptl_absorpt_correction_T_max  0.7457
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.979

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_av_unetI/netI     0.128
_diffrn_reflns_number            11894
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.932
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_reflns_Friedel_coverage         0
_reflns_number_total             3713
_reflns_number_gt                1773
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2016)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'Ortep for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0792P)²+0.1569P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3713
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1693
_refine_ls_R_factor_gt           0.0725
_refine_ls_wR_factor_ref         0.2063
_refine_ls_wR_factor_gt          0.1684
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.046

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2494(7) 0.6978(6) 0.36799(14) 0.0340(10) Uani 1 1 d . . . . .
C2 C 0.2791(7) 0.6379(6) 0.31610(12) 0.0318(9) Uani 1 1 d . . . . .
H2A H 0.130879 0.669843 0.297006 0.038 Uiso 1 1 calc R U . . .
H2B H 0.295219 0.500645 0.315508 0.038 Uiso 1 1 calc R U . . .
C3 C 0.4933(7) 0.7221(6) 0.28992(12) 0.0342(10) Uani 1 1 d . . . . .
H3A H 0.475597 0.859135 0.288547 0.041 Uiso 1 1 calc R U . . .
H3B H 0.643107 0.693548 0.308899 0.041 Uiso 1 1 calc R U . . .
C4 C 0.5105(7) 0.6448(5) 0.23758(12) 0.0305(9) Uani 1 1 d . . . . .
H4A H 0.535751 0.508658 0.239728 0.037 Uiso 1 1 calc R U . . .
H4B H 0.354522 0.665372 0.220031 0.037 Uiso 1 1 calc R U . . .
C5 C 0.7067(6) 0.7270(6) 0.20693(12) 0.0303(9) Uani 1 1 d . . . . .
H5A H 0.863854 0.703981 0.223766 0.036 Uiso 1 1 calc R U . . .
H5B H 0.683784 0.863406 0.204874 0.036 Uiso 1 1 calc R U . . .
C6 C 0.7122(7) 0.6474(6) 0.15494(12) 0.0339(10) Uani 1 1 d . . . . .
H6A H 0.553818 0.668424 0.13842 0.041 Uiso 1 1 calc R U . . .
H6B H 0.737247 0.511174 0.157112 0.041 Uiso 1 1 calc R U . . .
C7 C 0.9074(7) 0.7309(6) 0.12299(13) 0.0359(10) Uani 1 1 d . . . . .
H7A H 0.883004 0.867195 0.120788 0.043 Uiso 1 1 calc R U . . .
H7B H 1.066136 0.709179 0.139268 0.043 Uiso 1 1 calc R U . . .
C8 C 0.9088(8) 0.6505(7) 0.07136(13) 0.0446(11) Uani 1 1 d . . . . .
H8A H 0.750416 0.673037 0.055013 0.054 Uiso 1 1 calc R U . . .
H8B H 0.932025 0.514139 0.073579 0.054 Uiso 1 1 calc R U . . .
C9 C 1.1036(8) 0.7324(7) 0.03970(14) 0.0584(14) Uani 1 1 d . . . . .
H9A H 1.095465 0.674989 0.006785 0.088 Uiso 1 1 calc R U . . .
H9B H 1.079645 0.867041 0.036641 0.088 Uiso 1 1 calc R U . . .
H9C H 1.26138 0.708034 0.055219 0.088 Uiso 1 1 calc R U . . .
C10 C -0.0176(8) 0.6804(8) 0.43462(14) 0.0536(13) Uani 1 1 d . . . . .
H10A H -0.179467 0.636209 0.441993 0.08 Uiso 1 1 calc R U . . .
H10B H 0.100563 0.615196 0.455724 0.08 Uiso 1 1 calc R U . . .
H10C H -0.006915 0.814545 0.440977 0.08 Uiso 1 1 calc R U . . .
C11 C 0.6159(8) 0.2092(6) 0.39800(14) 0.0355(10) Uani 1 1 d . . . . .
C12 C 0.8142(7) 0.1424(6) 0.36758(12) 0.0347(10) Uani 1 1 d . . . . .
H12A H 0.805558 0.004908 0.365542 0.042 Uiso 1 1 calc R U . . .
H12B H 0.968518 0.175415 0.384409 0.042 Uiso 1 1 calc R U . . .
C13 C 0.8139(7) 0.2196(6) 0.31594(13) 0.0325(10) Uani 1 1 d . . . . .
H13A H 0.832135 0.356594 0.317828 0.039 Uiso 1 1 calc R U . . .
H13B H 0.656456 0.192561 0.299587 0.039 Uiso 1 1 calc R U . . .
C14 C 1.0108(7) 0.1414(6) 0.28452(13) 0.0328(9) Uani 1 1 d . . . . .
H14A H 0.98941 0.004894 0.281889 0.039 Uiso 1 1 calc R U . . .
H14B H 1.167688 0.164941 0.301492 0.039 Uiso 1 1 calc R U . . .
C15 C 1.0177(7) 0.2230(6) 0.23232(13) 0.0326(9) Uani 1 1 d . . . . .
H15A H 0.861665 0.198604 0.215115 0.039 Uiso 1 1 calc R U . . .
H15B H 1.038685 0.359575 0.234807 0.039 Uiso 1 1 calc R U . . .
C16 C 1.2166(7) 0.1437(6) 0.20179(13) 0.0337(10) Uani 1 1 d . . . . .
H16A H 1.196927 0.00686 0.199751 0.04 Uiso 1 1 calc R U . . .
H16B H 1.372754 0.169523 0.218818 0.04 Uiso 1 1 calc R U . . .
C17 C 1.2227(7) 0.2224(6) 0.14939(13) 0.0353(10) Uani 1 1 d . . . . .
H17A H 1.066918 0.196341 0.132268 0.042 Uiso 1 1 calc R U . . .
H17B H 1.242556 0.359211 0.151355 0.042 Uiso 1 1 calc R U . . .
C18 C 1.4232(7) 0.1420(6) 0.11912(14) 0.0423(11) Uani 1 1 d . . . . .
H18A H 1.578821 0.169112 0.13621 0.051 Uiso 1 1 calc R U . . .
H18B H 1.40422 0.005018 0.117633 0.051 Uiso 1 1 calc R U . . .
C19 C 1.4310(9) 0.2165(7) 0.06692(15) 0.0598(14) Uani 1 1 d . . . . .
H19A H 1.564509 0.15853 0.049659 0.09 Uiso 1 1 calc R U . . .
H19B H 1.279389 0.187383 0.049337 0.09 Uiso 1 1 calc R U . . .
H19C H 1.454222 0.351695 0.06794 0.09 Uiso 1 1 calc R U . . .
C20 C 0.4555(8) 0.2257(7) 0.47775(14) 0.0525(13) Uani 1 1 d . . . . .
H20A H 0.497751 0.19456 0.512137 0.079 Uiso 1 1 calc R U . . .
H20B H 0.426781 0.359896 0.475029 0.079 Uiso 1 1 calc R U . . .
H20C H 0.309773 0.157863 0.467399 0.079 Uiso 1 1 calc R U . . .
O1 O 0.0309(5) 0.6440(4) 0.38364(9) 0.0415(8) Uani 1 1 d . . . . .
O2 O 0.3894(5) 0.7839(5) 0.39343(10) 0.0521(9) Uani 1 1 d . . . . .
O3 O 0.6505(5) 0.1739(4) 0.44633(9) 0.0458(8) Uani 1 1 d . . . . .
O4 O 0.4348(5) 0.2840(5) 0.38264(10) 0.0528(9) Uani 1 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 O2 1.197(4) . ?
C1 O1 1.354(4) . ?
C1 C2 1.480(5) . ?
C2 C3 1.526(5) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C4 1.525(5) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 C5 1.508(5) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 C6 1.518(5) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 C7 1.528(5) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 C8 1.510(5) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 C9 1.517(6) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 O1 1.435(4) . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 O4 1.208(5) . ?
C11 O3 1.341(4) . ?
C11 C12 1.473(5) . ?
C12 C13 1.504(5) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 C14 1.512(5) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 C15 1.531(5) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C15 C16 1.509(5) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 C17 1.528(5) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 C18 1.515(5) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 C19 1.512(5) . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C20 O3 1.443(5) . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?

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
O2 C1 O1 122.9(3) . . ?
O2 C1 C2 127.3(4) . . ?
O1 C1 C2 109.7(3) . . ?
C1 C2 C3 115.6(3) . . ?
C1 C2 H2A 108.4 . . ?
C3 C2 H2A 108.4 . . ?
C1 C2 H2B 108.4 . . ?
C3 C2 H2B 108.4 . . ?
H2A C2 H2B 107.4 . . ?
C4 C3 C2 110.8(3) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 115.6(3) . . ?
C5 C4 H4A 108.4 . . ?
C3 C4 H4A 108.4 . . ?
C5 C4 H4B 108.4 . . ?
C3 C4 H4B 108.4 . . ?
H4A C4 H4B 107.4 . . ?
C4 C5 C6 113.2(3) . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C6 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C5 C6 C7 114.1(3) . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
C7 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C8 C7 C6 113.2(3) . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 C9 113.3(3) . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C11 O3 121.3(4) . . ?
O4 C11 C12 125.7(4) . . ?
O3 C11 C12 113.0(4) . . ?
C11 C12 C13 114.5(3) . . ?
C11 C12 H12A 108.6 . . ?
C13 C12 H12A 108.6 . . ?
C11 C12 H12B 108.6 . . ?
C13 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 C14 113.6(3) . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 C15 114.3(3) . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C16 C15 C14 113.3(3) . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 C17 113.6(3) . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
C17 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C16 113.2(3) . . ?
C18 C17 H17A 108.9 . . ?
C16 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.8 . . ?
C19 C18 C17 114.1(4) . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 O1 C10 116.2(3) . . ?
C11 O3 C20 115.6(3) . . ?

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 C1 C2 C3 -10.7(6) . . . . ?
O1 C1 C2 C3 167.9(3) . . . . ?
C1 C2 C3 C4 177.9(3) . . . . ?
C2 C3 C4 C5 176.4(3) . . . . ?
C3 C4 C5 C6 -178.9(3) . . . . ?
C4 C5 C6 C7 179.1(3) . . . . ?
C5 C6 C7 C8 -179.7(3) . . . . ?
C6 C7 C8 C9 -179.6(4) . . . . ?
O4 C11 C12 C13 16.4(6) . . . . ?
O3 C11 C12 C13 -165.5(3) . . . . ?
C11 C12 C13 C14 -176.9(3) . . . . ?
C12 C13 C14 C15 -178.3(3) . . . . ?
C13 C14 C15 C16 179.6(3) . . . . ?
C14 C15 C16 C17 179.2(3) . . . . ?
C15 C16 C17 C18 179.9(3) . . . . ?
C16 C17 C18 C19 179.4(3) . . . . ?
O2 C1 O1 C10 -5.7(6) . . . . ?
C2 C1 O1 C10 175.6(4) . . . . ?
O4 C11 O3 C20 1.9(6) . . . . ?
C12 C11 O3 C20 -176.3(4) . . . . ?

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
_geom_hbond_publ_flag
C2 H2B O4 0.99 2.5 3.225(5) 130 . yes
C20 H20A O2 0.98 2.62 3.569(5) 163 2_666 yes

####################################################################### 
# 
# 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_C7
_database_code_depnum_ccdc_archive 'CCDC 1590403'
_audit_update_record             
;
2018-09-24 deposited with the CCDC.
2018-11-05 downloaded from the CCDC.
;

_audit_creation_date             2018-09-06T12:02:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C8  H16  O2'
_chemical_formula_sum            'C8 H16 O2'
_chemical_formula_weight         144.21

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.173(3)
_cell_length_b                   5.6554(17)
_cell_length_c                   17.357(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.928(3)
_cell_angle_gamma                90
_cell_volume                     870.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5597
_cell_measurement_theta_min      3.78
_cell_measurement_theta_max      27.92
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_diffrn    1.101
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS
        (Sheldrick, 1996)
;

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

_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.6217
_exptl_absorpt_correction_T_max  0.7457
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.977

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_number            10012
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.775
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             1601
_reflns_number_gt                1355
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2016)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'Ortep for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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)+(0.0570P)²+0.3122P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1601
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1114
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.037

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.14347(15) 0.2838(3) 0.59048(8) 0.0270(3) Uani 1 1 d . . . . .
C2 C 0.17966(16) 0.3069(3) 0.51169(8) 0.0307(4) Uani 1 1 d . . . . .
H2A H 0.085841 0.283297 0.468936 0.037 Uiso 1 1 calc R U . . .
H2B H 0.250635 0.179277 0.506892 0.037 Uiso 1 1 calc R U . . .
C3 C 0.24791(16) 0.5408(3) 0.49840(8) 0.0293(4) Uani 1 1 d . . . . .
H3A H 0.338125 0.570954 0.542845 0.035 Uiso 1 1 calc R U . . .
H3B H 0.17414 0.668492 0.498512 0.035 Uiso 1 1 calc R U . . .
C4 C 0.29275(17) 0.5467(3) 0.42015(8) 0.0318(4) Uani 1 1 d . . . . .
H4A H 0.364402 0.415953 0.419856 0.038 Uiso 1 1 calc R U . . .
H4B H 0.20183 0.518382 0.375948 0.038 Uiso 1 1 calc R U . . .
C5 C 0.36460(16) 0.7766(3) 0.40491(8) 0.0315(4) Uani 1 1 d . . . . .
H5A H 0.450468 0.81153 0.451261 0.038 Uiso 1 1 calc R U . . .
H5B H 0.289897 0.905438 0.400806 0.038 Uiso 1 1 calc R U . . .
C6 C 0.42084(18) 0.7765(3) 0.33017(9) 0.0357(4) Uani 1 1 d . . . . .
H6A H 0.49643 0.648941 0.334414 0.043 Uiso 1 1 calc R U . . .
H6B H 0.335282 0.740545 0.283779 0.043 Uiso 1 1 calc R U . . .
C7 C 0.49069(19) 1.0069(3) 0.31549(10) 0.0404(4) Uani 1 1 d . . . . .
H7A H 0.524603 0.995206 0.266498 0.061 Uiso 1 1 calc R U . . .
H7B H 0.415873 1.133703 0.309849 0.061 Uiso 1 1 calc R U . . .
H7C H 0.577165 1.042016 0.36053 0.061 Uiso 1 1 calc R U . . .
C8 C 0.0771(2) 0.0138(3) 0.67895(9) 0.0390(4) Uani 1 1 d . . . . .
H8A H 0.05402 -0.154568 0.682218 0.058 Uiso 1 1 calc R U . . .
H8B H 0.164866 0.054996 0.722503 0.058 Uiso 1 1 calc R U . . .
H8C H -0.009897 0.108345 0.683382 0.058 Uiso 1 1 calc R U . . .
O1 O 0.10986(12) 0.06151(18) 0.60366(6) 0.0366(3) Uani 1 1 d . . . . .
O2 O 0.14355(14) 0.4402(2) 0.63660(6) 0.0455(4) Uani 1 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 O2 1.1926(17) . ?
C1 O1 1.3283(18) . ?
C1 C2 1.4938(19) . ?
C2 C3 1.506(2) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C4 1.5175(19) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 C5 1.512(2) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 C6 1.515(2) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 C7 1.503(2) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 O1 1.4400(18) . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?

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
O2 C1 O1 123.10(13) . . ?
O2 C1 C2 125.99(14) . . ?
O1 C1 C2 110.91(11) . . ?
C1 C2 C3 114.60(12) . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
C3 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
C2 C3 C4 112.05(11) . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C3 113.97(12) . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C4 C5 C6 114.16(12) . . ?
C4 C5 H5A 108.7 . . ?
C6 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
C6 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C7 C6 C5 113.52(13) . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
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 . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 O1 C8 116.48(11) . . ?

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 C1 C2 C3 11.4(2) . . . . ?
O1 C1 C2 C3 -168.72(12) . . . . ?
C1 C2 C3 C4 175.75(12) . . . . ?
C2 C3 C4 C5 -178.91(12) . . . . ?
C3 C4 C5 C6 175.37(12) . . . . ?
C4 C5 C6 C7 179.50(13) . . . . ?
O2 C1 O1 C8 -1.9(2) . . . . ?
C2 C1 O1 C8 178.19(12) . . . . ?

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
_geom_hbond_publ_flag
C8 H8A O2 0.98 2.62 3.416(2) 138 1_545 yes
C8 H8B O2 0.98 2.7 3.573(2) 149 2_546 yes

####################################################################### 
# 
# 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_C12
_database_code_depnum_ccdc_archive 'CCDC 1590409'
_audit_update_record             
;
2018-09-24 deposited with the CCDC.
2018-11-05 downloaded from the CCDC.
;

_audit_creation_date             2018-09-06T15:11:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C13  H26  O2'
_chemical_formula_sum            'C13 H26 O2'
_chemical_formula_weight         214.34

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_Int_Tables_number      60
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   67.940(6)
_cell_length_b                   7.1161(6)
_cell_length_c                   5.5638(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2689.9(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6557
_cell_measurement_theta_min      3
_cell_measurement_theta_max      28.11
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_diffrn    1.059
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS
        (Sheldrick, 1996)
;

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

_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.602
_exptl_absorpt_correction_T_max  0.7457
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.98

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_number            21984
_diffrn_reflns_limit_h_min       -80
_diffrn_reflns_limit_h_max       80
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.998
_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.963
_reflns_Friedel_coverage         0
_reflns_number_total             2419
_reflns_number_gt                1538
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2016)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'Ortep for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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)+(0.1181P)²+5.7640P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2419
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1383
_refine_ls_R_factor_gt           0.0973
_refine_ls_wR_factor_ref         0.2967
_refine_ls_wR_factor_gt          0.2764
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_restrained_S_all      1.09
_refine_ls_shift/su_max          0.034
_refine_ls_shift/su_mean         0.005
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.071

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.45118(6) 0.7375(5) 0.1448(6) 0.0289(9) Uani 1 1 d . . . . .
C2 C 0.43858(5) 0.7934(5) 0.3517(6) 0.0285(9) Uani 1 1 d . . . . .
H2A H 0.437846 0.932295 0.357517 0.034 Uiso 1 1 calc R U . . .
H2B H 0.444923 0.750441 0.502224 0.034 Uiso 1 1 calc R U . . .
C3 C 0.41795(5) 0.7155(5) 0.3420(6) 0.0257(9) Uani 1 1 d . . . . .
H3A H 0.418517 0.576754 0.352597 0.031 Uiso 1 1 calc R U . . .
H3B H 0.411914 0.748854 0.185815 0.031 Uiso 1 1 calc R U . . .
C4 C 0.40506(5) 0.7909(5) 0.5455(6) 0.0260(9) Uani 1 1 d . . . . .
H4A H 0.411444 0.761837 0.700993 0.031 Uiso 1 1 calc R U . . .
H4B H 0.404219 0.929364 0.531106 0.031 Uiso 1 1 calc R U . . .
C5 C 0.38435(5) 0.7105(5) 0.5469(6) 0.0264(9) Uani 1 1 d . . . . .
H5A H 0.385168 0.572339 0.565823 0.032 Uiso 1 1 calc R U . . .
H5B H 0.37808 0.736567 0.389839 0.032 Uiso 1 1 calc R U . . .
C6 C 0.37141(5) 0.7897(5) 0.7456(6) 0.0267(9) Uani 1 1 d . . . . .
H6A H 0.377775 0.764554 0.902395 0.032 Uiso 1 1 calc R U . . .
H6B H 0.370549 0.927686 0.725774 0.032 Uiso 1 1 calc R U . . .
C7 C 0.35075(5) 0.7092(5) 0.7501(6) 0.0285(9) Uani 1 1 d . . . . .
H7A H 0.351603 0.571343 0.771408 0.034 Uiso 1 1 calc R U . . .
H7B H 0.344421 0.733364 0.592801 0.034 Uiso 1 1 calc R U . . .
C8 C 0.33777(5) 0.7902(5) 0.9480(6) 0.0286(9) Uani 1 1 d . . . . .
H8A H 0.344067 0.766208 1.105518 0.034 Uiso 1 1 calc R U . . .
H8B H 0.336836 0.927978 0.926594 0.034 Uiso 1 1 calc R U . . .
C9 C 0.31720(5) 0.7081(5) 0.9505(6) 0.0296(9) Uani 1 1 d . . . . .
H9A H 0.318152 0.570258 0.972073 0.036 Uiso 1 1 calc R U . . .
H9B H 0.310932 0.731763 0.7928 0.036 Uiso 1 1 calc R U . . .
C10 C 0.30407(6) 0.7889(5) 1.1485(7) 0.0314(9) Uani 1 1 d . . . . .
H10A H 0.310298 0.765131 1.306522 0.038 Uiso 1 1 calc R U . . .
H10B H 0.303068 0.926691 1.127113 0.038 Uiso 1 1 calc R U . . .
C11 C 0.28371(5) 0.7057(6) 1.1484(7) 0.0362(10) Uani 1 1 d . . . . .
H11A H 0.284721 0.568246 1.172594 0.043 Uiso 1 1 calc R U . . .
H11B H 0.277597 0.727442 0.98925 0.043 Uiso 1 1 calc R U . . .
C12 C 0.27048(6) 0.7878(7) 1.3416(7) 0.0465(12) Uani 1 1 d . . . . .
H12A H 0.257476 0.728642 1.332904 0.07 Uiso 1 1 calc R U . . .
H12B H 0.276278 0.764269 1.500067 0.07 Uiso 1 1 calc R U . . .
H12C H 0.26915 0.923554 1.316621 0.07 Uiso 1 1 calc R U . . .
C13 C 0.48325(6) 0.7424(8) -0.0223(9) 0.0654(16) Uani 1 1 d . . . . .
H13A H 0.496764 0.778799 0.018033 0.098 Uiso 1 1 calc R U . . .
H13B H 0.482828 0.607676 -0.058576 0.098 Uiso 1 1 calc R U . . .
H13C H 0.47883 0.813711 -0.163016 0.098 Uiso 1 1 calc R U . . .
O1 O 0.47045(4) 0.7822(5) 0.1793(5) 0.0503(9) Uani 1 1 d . . . . .
O2 O 0.44593(4) 0.6711(5) -0.0402(5) 0.0495(9) Uani 1 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 O2 1.188(4) . ?
C1 O1 1.361(5) . ?
C1 C2 1.489(5) . ?
C2 C3 1.508(5) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C4 1.529(5) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 C5 1.519(5) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 C6 1.521(5) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 C7 1.516(5) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 C8 1.524(5) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 C9 1.514(5) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C10 1.530(5) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C11 1.505(5) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 C12 1.518(5) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 O1 1.448(5) . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?

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
O2 C1 O1 120.3(3) . . ?
O2 C1 C2 127.2(4) . . ?
O1 C1 C2 112.4(3) . . ?
C1 C2 C3 114.1(3) . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C2 C3 C4 112.2(3) . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C3 113.7(3) . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C4 C5 C6 113.6(3) . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C6 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C7 C6 C5 114.0(3) . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C6 C7 C8 113.9(3) . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C7 113.2(3) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 C10 113.5(3) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 112.8(3) . . ?
C11 C10 H10A 109 . . ?
C9 C10 H10A 109 . . ?
C11 C10 H10B 109 . . ?
C9 C10 H10B 109 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C12 113.1(3) . . ?
C10 C11 H11A 109 . . ?
C12 C11 H11A 109 . . ?
C10 C11 H11B 109 . . ?
C12 C11 H11B 109 . . ?
H11A C11 H11B 107.8 . . ?
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 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 O1 C13 115.0(3) . . ?

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 C1 C2 C3 14.9(6) . . . . ?
O1 C1 C2 C3 -169.3(3) . . . . ?
C1 C2 C3 C4 -174.8(3) . . . . ?
C2 C3 C4 C5 -178.0(3) . . . . ?
C3 C4 C5 C6 -178.5(3) . . . . ?
C4 C5 C6 C7 -179.5(3) . . . . ?
C5 C6 C7 C8 -179.5(3) . . . . ?
C6 C7 C8 C9 -179.9(3) . . . . ?
C7 C8 C9 C10 -179.9(3) . . . . ?
C8 C9 C10 C11 -180.0(3) . . . . ?
C9 C10 C11 C12 -179.0(3) . . . . ?
O2 C1 O1 C13 -0.1(6) . . . . ?
C2 C1 O1 C13 -176.2(4) . . . . ?

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
_geom_hbond_publ_flag
C2 H2B O2 0.99 2.61 3.529(4) 155 1_556 yes
C3 H3A O2 0.99 2.63 3.408(5) 135 7_566 yes

####################################################################### 
# 
# 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_C6
_database_code_depnum_ccdc_archive 'CCDC 1590404'
_audit_update_record             
;
2018-09-24 deposited with the CCDC.
2018-11-05 downloaded from the CCDC.
;

_audit_creation_date             2018-09-06T09:56:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C7  H14  O2'
_chemical_formula_sum            'C7 H14 O2'
_chemical_formula_weight         130.18

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   38.19(2)
_cell_length_b                   4.088(2)
_cell_length_c                   9.951(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.206(10)
_cell_angle_gamma                90
_cell_volume                     1553.5(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6081
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.76
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS
        (Sheldrick, 1996)
;

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

_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.6337
_exptl_absorpt_correction_T_max  0.7457

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.114
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_number            16225
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.201
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             1431
_reflns_number_gt                1244
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2016)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'Ortep for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1498P)²+4.4262P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1431
_refine_ls_number_parameters     85
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0841
_refine_ls_wR_factor_ref         0.2534
_refine_ls_wR_factor_gt          0.2448
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.054
_refine_ls_shift/su_mean         0.011
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.088

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.20407(7) 0.9282(8) 0.2453(4) 0.0392(9) Uani 1 1 d . . . . .
O2 O 0.16297(9) 0.6418(10) 0.1458(4) 0.0510(11) Uani 1 1 d . . . . .
C1 C 0.17218(10) 0.7909(10) 0.2416(4) 0.0279(10) Uani 1 1 d . . . . .
C2 C 0.15162(11) 0.8414(10) 0.3650(5) 0.0327(11) Uani 1 1 d . . . . .
H2A H 0.153698 1.074067 0.391424 0.039 Uiso 1 1 calc R U . . .
H2B H 0.162278 0.709001 0.437717 0.039 Uiso 1 1 calc R U . . .
C3 C 0.11317(10) 0.7564(10) 0.3563(5) 0.0311(10) Uani 1 1 d . . . . .
H3A H 0.110851 0.524896 0.328396 0.037 Uiso 1 1 calc R U . . .
H3B H 0.102139 0.893034 0.285741 0.037 Uiso 1 1 calc R U . . .
C4 C 0.09334(11) 0.8054(10) 0.4875(5) 0.0299(10) Uani 1 1 d . . . . .
H4A H 0.104488 0.669572 0.558024 0.036 Uiso 1 1 calc R U . . .
H4B H 0.095656 1.037108 0.515136 0.036 Uiso 1 1 calc R U . . .
C5 C 0.05470(11) 0.7199(11) 0.4803(5) 0.0339(11) Uani 1 1 d . . . . .
H5A H 0.043545 0.855669 0.409827 0.041 Uiso 1 1 calc R U . . .
H5B H 0.052376 0.488144 0.45279 0.041 Uiso 1 1 calc R U . . .
C6 C 0.03510(12) 0.7689(14) 0.6106(6) 0.0444(13) Uani 1 1 d . . . . .
H6A H 0.010609 0.7034 0.598511 0.067 Uiso 1 1 calc R U . . .
H6B H 0.036134 1.000039 0.636496 0.067 Uiso 1 1 calc R U . . .
H6C H 0.045862 0.635109 0.681289 0.067 Uiso 1 1 calc R U . . .
C7 C 0.22545(12) 0.8900(14) 0.1285(5) 0.0440(13) Uani 1 1 d . . . . .
H7A H 0.247328 1.012025 0.140584 0.066 Uiso 1 1 calc R U . . .
H7B H 0.212919 0.974159 0.049646 0.066 Uiso 1 1 calc R U . . .
H7C H 0.230755 0.657688 0.115277 0.066 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   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 1.342(5) . ?
O1 C7 1.431(6) . ?
O2 C1 1.184(6) . ?
C1 C2 1.474(7) . ?
C2 C3 1.511(6) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C4 1.525(7) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 C5 1.518(5) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 C6 1.513(7) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?

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 C7 116.9(4) . . ?
O2 C1 O1 120.3(4) . . ?
O2 C1 C2 125.8(4) . . ?
O1 C1 C2 113.9(4) . . ?
C1 C2 C3 116.1(4) . . ?
C1 C2 H2A 108.3 . . ?
C3 C2 H2A 108.3 . . ?
C1 C2 H2B 108.3 . . ?
C3 C2 H2B 108.3 . . ?
H2A C2 H2B 107.4 . . ?
C2 C3 C4 114.0(4) . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C3 114.5(4) . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
C3 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C6 C5 C4 114.4(4) . . ?
C6 C5 H5A 108.7 . . ?
C4 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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
C7 O1 C1 O2 1.2(6) . . . . ?
C7 O1 C1 C2 -179.8(4) . . . . ?
O2 C1 C2 C3 -13.5(7) . . . . ?
O1 C1 C2 C3 167.5(3) . . . . ?
C1 C2 C3 C4 178.6(4) . . . . ?
C2 C3 C4 C5 -179.8(4) . . . . ?
C3 C4 C5 C6 -180.0(4) . . . . ?

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
_geom_hbond_publ_flag
C2 H2B O2 0.99 2.52 3.448(6) 156 6_566 yes

####################################################################### 
# 
# 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_C13
_database_code_depnum_ccdc_archive 'CCDC 1590410'
_audit_update_record             
;
2018-09-24 deposited with the CCDC.
2018-11-05 downloaded from the CCDC.
;

_audit_creation_date             2018-09-10T15:57:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C14  H28  O2'
_chemical_formula_sum            'C14 H28 O2'
_chemical_formula_weight         228.36

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.5474(7)
_cell_length_b                   7.1923(9)
_cell_length_c                   36.076(5)
_cell_angle_alpha                89.983(3)
_cell_angle_beta                 89.626(4)
_cell_angle_gamma                89.903(3)
_cell_volume                     1439.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5618
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      28.08
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_diffrn    1.054
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS
        (Sheldrick, 1996)
;

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

_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_T_max  0.98
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.98

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.102
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_number            38217
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.888
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_reflns_Friedel_coverage         0
_reflns_number_total             5328
_reflns_number_gt                3260
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2016)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'Ortep for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1040P)²+2.2193P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5328
_refine_ls_number_parameters     294
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1574
_refine_ls_R_factor_gt           0.1012
_refine_ls_wR_factor_ref         0.2778
_refine_ls_wR_factor_gt          0.2479
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.063

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.2325(9) 0.6998(9) 0.40087(15) 0.0366(13) Uani 1 1 d . . . . .
C2 C -0.1926(10) 0.6392(8) 0.36142(14) 0.0346(13) Uani 1 1 d . . . . .
H2A H -0.338724 0.669863 0.347019 0.042 Uiso 1 1 calc R U . . .
H2B H -0.173463 0.502339 0.361023 0.042 Uiso 1 1 calc R U . . .
C3 C 0.0254(9) 0.7261(8) 0.34199(13) 0.0350(13) Uani 1 1 d . . . . .
H3A H 0.005251 0.862845 0.341128 0.042 Uiso 1 1 calc R U . . .
H3B H 0.172832 0.698251 0.356281 0.042 Uiso 1 1 calc R U . . .
C4 C 0.0539(10) 0.6511(8) 0.30258(13) 0.0329(13) Uani 1 1 d . . . . .
H4A H 0.07977 0.515061 0.30403 0.039 Uiso 1 1 calc R U . . .
H4B H -0.099277 0.671993 0.289273 0.039 Uiso 1 1 calc R U . . .
C5 C 0.2580(9) 0.7351(8) 0.27966(13) 0.0324(13) Uani 1 1 d . . . . .
H5A H 0.234582 0.871397 0.278203 0.039 Uiso 1 1 calc R U . . .
H5B H 0.412741 0.711764 0.292374 0.039 Uiso 1 1 calc R U . . .
C6 C 0.2727(9) 0.6565(7) 0.24061(14) 0.0321(13) Uani 1 1 d . . . . .
H6A H 0.294228 0.520113 0.242286 0.038 Uiso 1 1 calc R U . . .
H6B H 0.117314 0.680051 0.228101 0.038 Uiso 1 1 calc R U . . .
C7 C 0.4739(8) 0.7354(7) 0.21677(13) 0.0288(12) Uani 1 1 d . . . . .
H7A H 0.453006 0.871847 0.215038 0.035 Uiso 1 1 calc R U . . .
H7B H 0.629763 0.711304 0.229111 0.035 Uiso 1 1 calc R U . . .
C8 C 0.4842(9) 0.6560(8) 0.17823(14) 0.0306(13) Uani 1 1 d . . . . .
H8A H 0.328041 0.679973 0.165979 0.037 Uiso 1 1 calc R U . . .
H8B H 0.504781 0.519566 0.180041 0.037 Uiso 1 1 calc R U . . .
C9 C 0.6843(8) 0.7334(8) 0.15402(14) 0.0317(13) Uani 1 1 d . . . . .
H9A H 0.664188 0.869958 0.152321 0.038 Uiso 1 1 calc R U . . .
H9B H 0.840506 0.708929 0.166221 0.038 Uiso 1 1 calc R U . . .
C10 C 0.6941(8) 0.6549(8) 0.11544(15) 0.0336(13) Uani 1 1 d . . . . .
H10A H 0.536599 0.67672 0.103435 0.04 Uiso 1 1 calc R U . . .
H10B H 0.718323 0.518772 0.117111 0.04 Uiso 1 1 calc R U . . .
C11 C 0.8912(9) 0.7362(8) 0.09100(14) 0.0340(13) Uani 1 1 d . . . . .
H11A H 0.864999 0.871963 0.088845 0.041 Uiso 1 1 calc R U . . .
H11B H 1.048495 0.716806 0.103234 0.041 Uiso 1 1 calc R U . . .
C12 C 0.9034(10) 0.6537(10) 0.05248(16) 0.0443(15) Uani 1 1 d . . . . .
H12A H 0.74709 0.674618 0.040058 0.053 Uiso 1 1 calc R U . . .
H12B H 0.927846 0.51773 0.054577 0.053 Uiso 1 1 calc R U . . .
C13 C 1.1032(11) 0.7344(10) 0.02847(16) 0.0547(18) Uani 1 1 d . . . . .
H13A H 1.084114 0.869677 0.026965 0.082 Uiso 1 1 calc R U . . .
H13B H 1.094614 0.680915 0.003531 0.082 Uiso 1 1 calc R U . . .
H13C H 1.259873 0.704726 0.039407 0.082 Uiso 1 1 calc R U . . .
C14 C -0.5065(10) 0.6787(11) 0.45036(16) 0.0488(17) Uani 1 1 d . . . . .
H14A H -0.390654 0.612254 0.465937 0.073 Uiso 1 1 calc R U . . .
H14B H -0.669748 0.634253 0.455848 0.073 Uiso 1 1 calc R U . . .
H14C H -0.497097 0.812285 0.45546 0.073 Uiso 1 1 calc R U . . .
O1 O -0.4510(6) 0.6456(6) 0.41226(10) 0.0427(11) Uani 1 1 d . . . . .
O2 O -0.0915(7) 0.7853(7) 0.41923(10) 0.0523(12) Uani 1 1 d . . . . .
C15 C 0.1301(9) 0.2106(8) 0.42421(14) 0.0323(13) Uani 1 1 d . . . . .
C16 C 0.3321(9) 0.1460(8) 0.40168(14) 0.0345(13) Uani 1 1 d . . . . .
H16A H 0.326014 0.008716 0.40011 0.041 Uiso 1 1 calc R U . . .
H16B H 0.484242 0.180078 0.414147 0.041 Uiso 1 1 calc R U . . .
C17 C 0.3353(9) 0.2255(8) 0.36270(13) 0.0331(13) Uani 1 1 d . . . . .
H17A H 0.352655 0.362295 0.364042 0.04 Uiso 1 1 calc R U . . .
H17B H 0.179845 0.197948 0.350558 0.04 Uiso 1 1 calc R U . . .
C18 C 0.5404(9) 0.1454(8) 0.33939(14) 0.0341(13) Uani 1 1 d . . . . .
H18A H 0.518302 0.009344 0.337037 0.041 Uiso 1 1 calc R U . . .
H18B H 0.694997 0.167221 0.352221 0.041 Uiso 1 1 calc R U . . .
C19 C 0.5529(9) 0.2318(8) 0.30064(13) 0.0312(13) Uani 1 1 d . . . . .
H19A H 0.574155 0.367874 0.30304 0.037 Uiso 1 1 calc R U . . .
H19B H 0.398354 0.209574 0.287825 0.037 Uiso 1 1 calc R U . . .
C20 C 0.7594(9) 0.1525(8) 0.27703(14) 0.0330(13) Uani 1 1 d . . . . .
H20A H 0.913758 0.176116 0.289793 0.04 Uiso 1 1 calc R U . . .
H20B H 0.739109 0.016179 0.275037 0.04 Uiso 1 1 calc R U . . .
C21 C 0.7729(9) 0.2343(8) 0.23842(14) 0.0313(13) Uani 1 1 d . . . . .
H21A H 0.793076 0.370626 0.240482 0.038 Uiso 1 1 calc R U . . .
H21B H 0.618137 0.210993 0.225748 0.038 Uiso 1 1 calc R U . . .
C22 C 0.9762(9) 0.1571(8) 0.21464(14) 0.0316(13) Uani 1 1 d . . . . .
H22A H 1.13131 0.182244 0.22708 0.038 Uiso 1 1 calc R U . . .
H22B H 0.957681 0.020467 0.212891 0.038 Uiso 1 1 calc R U . . .
C23 C 0.9866(8) 0.2367(8) 0.17598(14) 0.0300(12) Uani 1 1 d . . . . .
H23A H 1.007867 0.373085 0.177645 0.036 Uiso 1 1 calc R U . . .
H23B H 0.830934 0.213012 0.163577 0.036 Uiso 1 1 calc R U . . .
C24 C 1.1895(9) 0.1557(8) 0.15231(14) 0.0317(12) Uani 1 1 d . . . . .
H24A H 1.345002 0.181351 0.164606 0.038 Uiso 1 1 calc R U . . .
H24B H 1.169752 0.019022 0.15119 0.038 Uiso 1 1 calc R U . . .
C25 C 1.2008(9) 0.2304(8) 0.11335(14) 0.0345(13) Uani 1 1 d . . . . .
H25A H 1.221624 0.366974 0.114417 0.041 Uiso 1 1 calc R U . . .
H25B H 1.045377 0.205103 0.10103 0.041 Uiso 1 1 calc R U . . .
C26 C 1.4029(9) 0.1481(9) 0.09005(15) 0.0419(15) Uani 1 1 d . . . . .
H26A H 1.558099 0.173574 0.102436 0.05 Uiso 1 1 calc R U . . .
H26B H 1.382133 0.011531 0.089131 0.05 Uiso 1 1 calc R U . . .
C27 C 1.4167(12) 0.2213(10) 0.05081(16) 0.0572(19) Uani 1 1 d . . . . .
H27A H 1.267734 0.190331 0.037739 0.086 Uiso 1 1 calc R U . . .
H27B H 1.554282 0.164293 0.037936 0.086 Uiso 1 1 calc R U . . .
H27C H 1.437038 0.356556 0.051305 0.086 Uiso 1 1 calc R U . . .
C28 C -0.0412(11) 0.2252(10) 0.48377(15) 0.0532(18) Uani 1 1 d . . . . .
H28A H -0.082004 0.356304 0.479856 0.08 Uiso 1 1 calc R U . . .
H28B H 0.003273 0.205818 0.509731 0.08 Uiso 1 1 calc R U . . .
H28C H -0.180855 0.147675 0.477814 0.08 Uiso 1 1 calc R U . . .
O3 O 0.1555(7) 0.1755(6) 0.46047(10) 0.0426(10) Uani 1 1 d . . . . .
O4 O -0.0506(7) 0.2870(6) 0.41328(11) 0.0511(12) Uani 1 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 O2 1.199(6) . ?
C1 O1 1.336(6) . ?
C1 C2 1.504(7) . ?
C2 C3 1.528(7) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C4 1.528(7) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 C5 1.523(7) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 C6 1.520(7) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 C7 1.515(7) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 C8 1.504(7) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 C9 1.515(7) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C10 1.503(7) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C11 1.518(7) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 C12 1.512(8) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 C13 1.518(8) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 O1 1.426(6) . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 O4 1.210(6) . ?
C15 O3 1.341(6) . ?
C15 C16 1.456(7) . ?
C16 C17 1.518(7) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 C18 1.523(7) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 C19 1.531(7) . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
C19 C20 1.532(7) . ?
C19 H19A 0.99 . ?
C19 H19B 0.99 . ?
C20 C21 1.513(7) . ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?
C21 C22 1.517(7) . ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?
C22 C23 1.508(7) . ?
C22 H22A 0.99 . ?
C22 H22B 0.99 . ?
C23 C24 1.524(7) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C24 C25 1.506(7) . ?
C24 H24A 0.99 . ?
C24 H24B 0.99 . ?
C25 C26 1.516(7) . ?
C25 H25A 0.99 . ?
C25 H25B 0.99 . ?
C26 C27 1.512(8) . ?
C26 H26A 0.99 . ?
C26 H26B 0.99 . ?
C27 H27A 0.98 . ?
C27 H27B 0.98 . ?
C27 H27C 0.98 . ?
C28 O3 1.418(6) . ?
C28 H28A 0.98 . ?
C28 H28B 0.98 . ?
C28 H28C 0.98 . ?

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
O2 C1 O1 125.1(5) . . ?
O2 C1 C2 125.4(5) . . ?
O1 C1 C2 109.5(4) . . ?
C1 C2 C3 115.2(5) . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
C3 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C4 C3 C2 111.0(4) . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108 . . ?
C5 C4 C3 115.9(4) . . ?
C5 C4 H4A 108.3 . . ?
C3 C4 H4A 108.3 . . ?
C5 C4 H4B 108.3 . . ?
C3 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?
C6 C5 C4 113.0(4) . . ?
C6 C5 H5A 109 . . ?
C4 C5 H5A 109 . . ?
C6 C5 H5B 109 . . ?
C4 C5 H5B 109 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C5 114.9(4) . . ?
C7 C6 H6A 108.5 . . ?
C5 C6 H6A 108.5 . . ?
C7 C6 H6B 108.5 . . ?
C5 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
C8 C7 C6 113.9(4) . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 C9 114.6(4) . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C8 114.7(4) . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C8 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 C11 114.5(4) . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C10 114.2(4) . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 C13 113.7(5) . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 O1 C14 115.9(4) . . ?
O4 C15 O3 119.7(5) . . ?
O4 C15 C16 126.7(5) . . ?
O3 C15 C16 113.6(4) . . ?
C15 C16 C17 113.7(5) . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
C17 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 C18 111.9(4) . . ?
C16 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
C16 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 C19 112.4(4) . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 C20 112.7(4) . . ?
C18 C19 H19A 109 . . ?
C20 C19 H19A 109 . . ?
C18 C19 H19B 109 . . ?
C20 C19 H19B 109 . . ?
H19A C19 H19B 107.8 . . ?
C21 C20 C19 113.6(4) . . ?
C21 C20 H20A 108.8 . . ?
C19 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
C19 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C20 C21 C22 114.3(4) . . ?
C20 C21 H21A 108.7 . . ?
C22 C21 H21A 108.7 . . ?
C20 C21 H21B 108.7 . . ?
C22 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C23 C22 C21 114.1(4) . . ?
C23 C22 H22A 108.7 . . ?
C21 C22 H22A 108.7 . . ?
C23 C22 H22B 108.7 . . ?
C21 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C22 C23 C24 113.4(4) . . ?
C22 C23 H23A 108.9 . . ?
C24 C23 H23A 108.9 . . ?
C22 C23 H23B 108.9 . . ?
C24 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C25 C24 C23 114.4(4) . . ?
C25 C24 H24A 108.7 . . ?
C23 C24 H24A 108.7 . . ?
C25 C24 H24B 108.7 . . ?
C23 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C24 C25 C26 113.9(5) . . ?
C24 C25 H25A 108.8 . . ?
C26 C25 H25A 108.8 . . ?
C24 C25 H25B 108.8 . . ?
C26 C25 H25B 108.8 . . ?
H25A C25 H25B 107.7 . . ?
C27 C26 C25 114.6(5) . . ?
C27 C26 H26A 108.6 . . ?
C25 C26 H26A 108.6 . . ?
C27 C26 H26B 108.6 . . ?
C25 C26 H26B 108.6 . . ?
H26A C26 H26B 107.6 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O3 C28 H28A 109.5 . . ?
O3 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O3 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C15 O3 C28 116.5(4) . . ?

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 C1 C2 C3 -11.7(9) . . . . ?
O1 C1 C2 C3 167.5(5) . . . . ?
C1 C2 C3 C4 178.3(5) . . . . ?
C2 C3 C4 C5 176.9(4) . . . . ?
C3 C4 C5 C6 -179.0(5) . . . . ?
C4 C5 C6 C7 -179.8(4) . . . . ?
C5 C6 C7 C8 -179.8(4) . . . . ?
C6 C7 C8 C9 180.0(4) . . . . ?
C7 C8 C9 C10 -179.7(4) . . . . ?
C8 C9 C10 C11 178.6(4) . . . . ?
C9 C10 C11 C12 178.8(5) . . . . ?
C10 C11 C12 C13 -179.3(5) . . . . ?
O2 C1 O1 C14 -6.2(9) . . . . ?
C2 C1 O1 C14 174.6(5) . . . . ?
O4 C15 C16 C17 15.3(9) . . . . ?
O3 C15 C16 C17 -165.8(5) . . . . ?
C15 C16 C17 C18 -176.5(5) . . . . ?
C16 C17 C18 C19 -177.1(4) . . . . ?
C17 C18 C19 C20 179.8(4) . . . . ?
C18 C19 C20 C21 179.2(4) . . . . ?
C19 C20 C21 C22 -179.9(4) . . . . ?
C20 C21 C22 C23 179.1(4) . . . . ?
C21 C22 C23 C24 -179.2(4) . . . . ?
C22 C23 C24 C25 178.9(4) . . . . ?
C23 C24 C25 C26 -179.8(4) . . . . ?
C24 C25 C26 C27 179.9(5) . . . . ?
O4 C15 O3 C28 2.5(8) . . . . ?
C16 C15 O3 C28 -176.5(5) . . . . ?

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
_geom_hbond_publ_flag
C2 H2B O4 0.99 2.54 3.248(7) 129 . yes
C16 H16B O4 0.99 2.69 3.600(7) 152 1_655 yes
C28 H28B O2 0.98 2.61 3.582(7) 170 2_566 yes

####################################################################### 
# 
# 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_C10
_database_code_depnum_ccdc_archive 'CCDC 1590407'
_audit_update_record             
;
2018-09-24 deposited with the CCDC.
2018-11-05 downloaded from the CCDC.
;

_audit_creation_date             2018-09-06T14:41:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C11  H22  O2'
_chemical_formula_sum            'C11 H22 O2'
_chemical_formula_weight         186.28

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_Int_Tables_number      60
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   58.86(2)
_cell_length_b                   7.100(3)
_cell_length_c                   5.574(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2329.4(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5478
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      28.09
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_diffrn    1.062
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS
        (Sheldrick, 1996)
;

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

_exptl_absorpt_coefficient_mu    0.07
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.5607
_exptl_absorpt_correction_T_max  0.7457
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.979

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_number            18016
_diffrn_reflns_limit_h_min       -71
_diffrn_reflns_limit_h_max       71
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_reflns_Friedel_coverage         0
_reflns_number_total             2150
_reflns_number_gt                1462
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2016)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'Ortep for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2150
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1867
_refine_ls_R_factor_gt           0.1548
_refine_ls_wR_factor_ref         0.4772
_refine_ls_wR_factor_gt          0.4634
_refine_ls_goodness_of_fit_ref   1.861
_refine_ls_restrained_S_all      1.861
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.638
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.113

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.05588(8) 0.2395(7) 0.8571(10) 0.0275(13) Uani 1 1 d . . . . .
C2 C 0.07028(8) 0.2929(7) 0.6490(9) 0.0273(13) Uani 1 1 d . . . . .
H2A H 0.07108 0.432034 0.639868 0.033 Uiso 1 1 calc R U . . .
H2B H 0.062931 0.24741 0.500127 0.033 Uiso 1 1 calc R U . . .
C3 C 0.09429(7) 0.2148(6) 0.6604(9) 0.0245(13) Uani 1 1 d . . . . .
H3A H 0.101141 0.247873 0.816993 0.029 Uiso 1 1 calc R U . . .
H3B H 0.093706 0.075756 0.648883 0.029 Uiso 1 1 calc R U . . .
C4 C 0.10915(8) 0.2913(7) 0.4600(9) 0.0243(13) Uani 1 1 d . . . . .
H4A H 0.110142 0.429962 0.476037 0.029 Uiso 1 1 calc R U . . .
H4B H 0.101819 0.263464 0.304071 0.029 Uiso 1 1 calc R U . . .
C5 C 0.13310(8) 0.2098(7) 0.4587(9) 0.0250(13) Uani 1 1 d . . . . .
H5A H 0.132107 0.071623 0.437673 0.03 Uiso 1 1 calc R U . . .
H5B H 0.140242 0.23424 0.616488 0.03 Uiso 1 1 calc R U . . .
C6 C 0.14832(7) 0.2910(7) 0.2618(9) 0.0256(13) Uani 1 1 d . . . . .
H6A H 0.141069 0.268314 0.104134 0.031 Uiso 1 1 calc R U . . .
H6B H 0.149518 0.428936 0.284324 0.031 Uiso 1 1 calc R U . . .
C7 C 0.17197(8) 0.2074(7) 0.2590(9) 0.0280(13) Uani 1 1 d . . . . .
H7A H 0.170766 0.069526 0.235923 0.034 Uiso 1 1 calc R U . . .
H7B H 0.179192 0.2297 0.41685 0.034 Uiso 1 1 calc R U . . .
C8 C 0.18722(8) 0.2888(7) 0.0629(9) 0.0265(13) Uani 1 1 d . . . . .
H8A H 0.180015 0.266214 -0.095003 0.032 Uiso 1 1 calc R U . . .
H8B H 0.188384 0.426751 0.085674 0.032 Uiso 1 1 calc R U . . .
C9 C 0.21095(8) 0.2056(8) 0.0603(10) 0.0332(14) Uani 1 1 d . . . . .
H9A H 0.209775 0.067649 0.037311 0.04 Uiso 1 1 calc R U . . .
H9B H 0.21813 0.227897 0.218386 0.04 Uiso 1 1 calc R U . . .
C10 C 0.22624(9) 0.2863(8) -0.1343(11) 0.0433(16) Uani 1 1 d . . . . .
H10A H 0.240434 0.214382 -0.140535 0.065 Uiso 1 1 calc R U . . .
H10B H 0.229609 0.418428 -0.097953 0.065 Uiso 1 1 calc R U . . .
H10C H 0.218508 0.278119 -0.289651 0.065 Uiso 1 1 calc R U . . .
C11 C 0.01903(9) 0.2433(11) 1.0247(13) 0.060(2) Uani 1 1 d . . . . .
H11A H 0.003258 0.271071 0.980948 0.09 Uiso 1 1 calc R U . . .
H11B H 0.02358 0.32334 1.159689 0.09 Uiso 1 1 calc R U . . .
H11C H 0.020339 0.110626 1.071112 0.09 Uiso 1 1 calc R U . . .
O1 O 0.03371(6) 0.2802(6) 0.8211(7) 0.0465(13) Uani 1 1 d . . . . .
O2 O 0.06213(6) 0.1715(6) 1.0415(7) 0.0401(12) Uani 1 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 O2 1.194(6) . ?
C1 O1 1.351(5) . ?
C1 C2 1.486(7) . ?
C2 C3 1.520(6) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C4 1.519(7) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 C5 1.524(6) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 C6 1.530(7) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 C7 1.513(6) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 C8 1.528(7) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 C9 1.517(6) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C10 1.521(7) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 O1 1.450(7) . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?

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
O2 C1 O1 120.8(5) . . ?
O2 C1 C2 126.9(4) . . ?
O1 C1 C2 112.3(4) . . ?
C1 C2 C3 113.9(4) . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 C2 112.0(4) . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C3 C4 C5 113.6(4) . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C4 C5 C6 113.7(4) . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C7 C6 C5 113.5(4) . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 C8 113.6(4) . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C7 113.6(4) . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 C10 113.9(5) . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 O1 C11 114.9(4) . . ?

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 C1 C2 C3 13.0(8) . . . . ?
O1 C1 C2 C3 -168.3(4) . . . . ?
C1 C2 C3 C4 -173.3(4) . . . . ?
C2 C3 C4 C5 -177.5(4) . . . . ?
C3 C4 C5 C6 -178.3(4) . . . . ?
C4 C5 C6 C7 -179.1(4) . . . . ?
C5 C6 C7 C8 -179.8(4) . . . . ?
C6 C7 C8 C9 179.8(4) . . . . ?
C7 C8 C9 C10 -179.9(4) . . . . ?
O2 C1 O1 C11 2.8(8) . . . . ?
C2 C1 O1 C11 -175.9(5) . . . . ?

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
_geom_hbond_publ_flag
C2 H2B O2 0.99 2.61 3.527(7) 154 1_554 yes
C3 H3B O2 0.99 2.63 3.398(6) 135 8 yes

