# 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_1_C6H6
_database_code_depnum_ccdc_archive 'CCDC 1855335'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 O2'
_chemical_formula_weight         218.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_H-M_alt        'P 32 2 1'
_space_group_name_Hall           'P 32 2"'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'
'y, x, -z'

_cell_length_a                   14.014(3)
_cell_length_b                   14.014(3)
_cell_length_c                   6.5964(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1121.9(5)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2096
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      17.50

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.969
_exptl_crystal_F_000             354
_exptl_transmission_factor_min   0.989
_exptl_transmission_factor_max   0.993
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.063
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            3435
_diffrn_reflns_av_unetI/netI     0.1296
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         1.678
_diffrn_reflns_theta_max         23.728
_diffrn_reflns_theta_full        23.728
_diffrn_measured_fraction_theta_max 0.789
_diffrn_measured_fraction_theta_full 0.790
_diffrn_reflns_Laue_measured_fraction_max 0.789
_diffrn_reflns_Laue_measured_fraction_full 0.790
_diffrn_reflns_point_group_measured_fraction_max 0.701
_diffrn_reflns_point_group_measured_fraction_full 0.703
_reflns_number_total             813
_reflns_number_gt                433
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.566
_reflns_Friedel_fraction_max     0.587
_reflns_Friedel_fraction_full    0.589

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.000 0.000 -0.033 284.7 88.7
_platon_squeeze_details          
; ?
;
_computing_data_collection       'Bruker SMART APEX-II'
_computing_cell_refinement       'Bruker SMART APEX-II'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1520P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 139 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   2.2(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         813
_refine_ls_number_parameters     73
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1308
_refine_ls_R_factor_gt           0.0839
_refine_ls_wR_factor_ref         0.2382
_refine_ls_wR_factor_gt          0.2217
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.6801(4) 0.4045(5) 0.1674(9) 0.058(2) Uani 1 1 d . . . . .
H1 H 0.683615 0.379185 0.280802 0.070 Uiso 1 1 calc R U . . .
C1 C 0.7359(9) 0.5211(8) 0.1767(17) 0.059(3) Uani 1 1 d . . . . .
C2 C 0.8557(10) 0.5715(9) 0.220(2) 0.071(3) Uani 1 1 d . . . . .
H2A H 0.888009 0.650295 0.255737 0.085 Uiso 1 1 calc R U . . .
H2B H 0.868298 0.532959 0.333801 0.085 Uiso 1 1 calc R U . . .
C3 C 0.9042(12) 0.5592(10) 0.035(4) 0.118(6) Uani 1 1 d . . . . .
H3B H 0.904909 0.488909 0.034776 0.141 Uiso 1 1 calc R U . . .
H3A H 0.980707 0.620826 0.018313 0.141 Uiso 1 1 calc R U . . .
C4 C 0.8236(13) 0.5605(11) -0.150(3) 0.119(5) Uani 1 1 d . . . . .
H4A H 0.864061 0.626509 -0.236921 0.143 Uiso 1 1 calc R U . . .
H4B H 0.795560 0.493762 -0.235791 0.143 Uiso 1 1 calc R U . . .
C5 C 0.7289(8) 0.5628(8) -0.0379(18) 0.068(3) Uani 1 1 d . . . . .
H5B H 0.657064 0.513250 -0.102822 0.082 Uiso 1 1 calc R U . . .
H5A H 0.740182 0.638374 -0.032450 0.082 Uiso 1 1 calc R U . . .
C6 C 0.6807(8) 0.5615(8) 0.3178(19) 0.055(3) Uani 1 1 d . . . . .
C7 C 0.6423(8) 0.5988(9) 0.433(2) 0.060(3) Uani 1 1 d . . . . .


_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 1.416(11) . ?
O1 H1 0.8400 . ?
C1 C2 1.489(15) . ?
C1 C6 1.491(17) . ?
C1 C5 1.554(14) . ?
C2 C3 1.45(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.67(3) . ?
C3 H3B 0.9900 . ?
C3 H3A 0.9900 . ?
C4 C5 1.534(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5B 0.9900 . ?
C5 H5A 0.9900 . ?
C6 C7 1.192(12) . ?
C7 C7 1.38(3) 6_556 ?

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 H1 109.5 . . ?
O1 C1 C2 113.4(9) . . ?
O1 C1 C6 111.9(8) . . ?
C2 C1 C6 112.1(9) . . ?
O1 C1 C5 107.0(8) . . ?
C2 C1 C5 105.4(9) . . ?
C6 C1 C5 106.5(9) . . ?
C3 C2 C1 105.4(12) . . ?
C3 C2 H2A 110.7 . . ?
C1 C2 H2A 110.7 . . ?
C3 C2 H2B 110.7 . . ?
C1 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?
C2 C3 C4 104.8(12) . . ?
C2 C3 H3B 110.8 . . ?
C4 C3 H3B 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3A 110.8 . . ?
H3B C3 H3A 108.9 . . ?
C5 C4 C3 104.2(13) . . ?
C5 C4 H4A 110.9 . . ?
C3 C4 H4A 110.9 . . ?
C5 C4 H4B 110.9 . . ?
C3 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
C4 C5 C1 102.4(10) . . ?
C4 C5 H5B 111.3 . . ?
C1 C5 H5B 111.3 . . ?
C4 C5 H5A 111.3 . . ?
C1 C5 H5A 111.3 . . ?
H5B C5 H5A 109.2 . . ?
C7 C6 C1 176.3(11) . . ?
C6 C7 C7 179.4(12) . 6_556 ?

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_1_140K
_database_code_depnum_ccdc_archive 'CCDC 1855341'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
; 
1,4-Bis(1-hydroxycyclopentyl)buta-1,3-diyne 
;
_chemical_name_common            ?
_chemical_melting_point          406K
_chemical_formula_moiety         'C14 H18 O2'
_chemical_formula_sum            'C14 H18 O2'
_chemical_formula_weight         218.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   7.1163(6)
_cell_length_b                   11.9960(11)
_cell_length_c                   14.4685(13)
_cell_angle_alpha                90
_cell_angle_beta                 97.4920(10)
_cell_angle_gamma                90
_cell_volume                     1224.59(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    2400
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      27.22

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9712
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            6954
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.213
_diffrn_reflns_theta_max         27.451
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2650
_reflns_number_gt                2102
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART APEX-II'
_computing_cell_refinement       'Bruker SMART APEX-II'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0662P)²+0.6874P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2650
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1566
_refine_ls_wR_factor_gt          0.1449
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.06834(19) 0.83219(10) 0.50953(9) 0.0368(3) Uani 1 1 d . . . . .
H1 H 0.076631 0.864229 0.458593 0.044 Uiso 1 1 calc R U . . .
C7 C -0.2489(3) 0.65747(15) 0.37428(13) 0.0334(4) Uani 1 1 d . . . . .
C9 C -0.5236(3) 0.58355(15) 0.25619(13) 0.0311(4) Uani 1 1 d . . . . .
C8 C -0.3979(3) 0.62054(15) 0.31095(13) 0.0327(4) Uani 1 1 d . . . . .
C2 C 0.0553(3) 0.66169(15) 0.59114(13) 0.0330(4) Uani 1 1 d . . . . .
H2A H -0.026687 0.703598 0.629176 0.040 Uiso 1 1 calc R U . . .
H2B H 0.012648 0.583126 0.586185 0.040 Uiso 1 1 calc R U . . .
C10 C -0.6754(3) 0.53517(14) 0.18951(12) 0.0298(4) Uani 1 1 d . . . . .
C1 C 0.0525(2) 0.71428(14) 0.49469(12) 0.0282(4) Uani 1 1 d . . . . .
C6 C -0.1166(3) 0.68617(15) 0.42919(13) 0.0333(4) Uani 1 1 d . . . . .
C5 C 0.2344(3) 0.66713(16) 0.46202(13) 0.0352(4) Uani 1 1 d . . . . .
H5A H 0.207805 0.595604 0.428748 0.042 Uiso 1 1 calc R U . . .
H5B H 0.286696 0.720306 0.419663 0.042 Uiso 1 1 calc R U . . .
O2 O -0.5994(3) 0.50536(14) 0.10661(11) 0.0619(5) Uani 1 1 d . . . . .
H2 H -0.556002 0.562455 0.083297 0.074 Uiso 1 1 calc R U . . .
C11 C -0.7593(3) 0.42823(16) 0.22476(14) 0.0368(4) Uani 1 1 d . . . . .
H11A H -0.679609 0.362904 0.214490 0.044 Uiso 1 1 calc R U . . .
H11B H -0.771057 0.433839 0.292032 0.044 Uiso 1 1 calc R U . . .
C3 C 0.2633(3) 0.66946(16) 0.63308(13) 0.0369(5) Uani 1 1 d . . . . .
H3A H 0.294536 0.611921 0.681711 0.044 Uiso 1 1 calc R U . . .
H3B H 0.292218 0.743879 0.660940 0.044 Uiso 1 1 calc R U . . .
C4 C 0.3738(3) 0.6498(2) 0.55057(15) 0.0455(5) Uani 1 1 d . . . . .
H4A H 0.480575 0.703011 0.552554 0.055 Uiso 1 1 calc R U . . .
H4B H 0.425427 0.573033 0.552484 0.055 Uiso 1 1 calc R U . . .
C12 C -0.9544(3) 0.41896(19) 0.16682(17) 0.0489(6) Uani 1 1 d . . . . .
H12A H -0.945708 0.376668 0.108768 0.059 Uiso 1 1 calc R U . . .
H12B H -1.044340 0.380276 0.202630 0.059 Uiso 1 1 calc R U . . .
C14 C -0.8473(3) 0.61173(18) 0.16837(18) 0.0515(6) Uani 1 1 d . . . . .
H14A H -0.832266 0.661128 0.115010 0.062 Uiso 1 1 calc R U . . .
H14B H -0.862879 0.658532 0.223215 0.062 Uiso 1 1 calc R U . . .
C13 C -1.0184(4) 0.5350(2) 0.1448(3) 0.0759(9) Uani 1 1 d . . . . .
H13A H -1.120188 0.555815 0.182162 0.091 Uiso 1 1 calc R U . . .
H13B H -1.068594 0.541588 0.077956 0.091 Uiso 1 1 calc R U . . .


_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 1.433(2) . ?
O1 H1 0.8400 . ?
C7 C6 1.200(3) . ?
C7 C8 1.381(3) . ?
C9 C8 1.200(3) . ?
C9 C10 1.471(3) . ?
C2 C3 1.527(3) . ?
C2 C1 1.529(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C10 O2 1.424(2) . ?
C10 C14 1.529(3) . ?
C10 C11 1.530(2) . ?
C1 C6 1.470(3) . ?
C1 C5 1.543(2) . ?
C5 C4 1.529(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
O2 H2 0.8400 . ?
C11 C12 1.529(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C3 C4 1.531(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C12 C13 1.486(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 C13 1.529(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

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 H1 109.5 . . ?
C6 C7 C8 177.8(2) . . ?
C8 C9 C10 178.44(19) . . ?
C9 C8 C7 176.9(2) . . ?
C3 C2 C1 103.56(15) . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
O2 C10 C9 108.94(15) . . ?
O2 C10 C14 111.35(17) . . ?
C9 C10 C14 113.23(15) . . ?
O2 C10 C11 106.12(14) . . ?
C9 C10 C11 113.43(15) . . ?
C14 C10 C11 103.49(16) . . ?
O1 C1 C6 111.40(14) . . ?
O1 C1 C2 106.20(14) . . ?
C6 C1 C2 113.96(15) . . ?
O1 C1 C5 110.78(14) . . ?
C6 C1 C5 111.56(15) . . ?
C2 C1 C5 102.50(14) . . ?
C7 C6 C1 175.98(19) . . ?
C4 C5 C1 105.79(15) . . ?
C4 C5 H5A 110.6 . . ?
C1 C5 H5A 110.6 . . ?
C4 C5 H5B 110.6 . . ?
C1 C5 H5B 110.6 . . ?
H5A C5 H5B 108.7 . . ?
C10 O2 H2 109.5 . . ?
C12 C11 C10 104.14(15) . . ?
C12 C11 H11A 110.9 . . ?
C10 C11 H11A 110.9 . . ?
C12 C11 H11B 110.9 . . ?
C10 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
C2 C3 C4 104.50(15) . . ?
C2 C3 H3A 110.9 . . ?
C4 C3 H3A 110.9 . . ?
C2 C3 H3B 110.9 . . ?
C4 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
C5 C4 C3 106.81(16) . . ?
C5 C4 H4A 110.4 . . ?
C3 C4 H4A 110.4 . . ?
C5 C4 H4B 110.4 . . ?
C3 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
C13 C12 C11 106.27(18) . . ?
C13 C12 H12A 110.5 . . ?
C11 C12 H12A 110.5 . . ?
C13 C12 H12B 110.5 . . ?
C11 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C10 C14 C13 106.05(18) . . ?
C10 C14 H14A 110.5 . . ?
C13 C14 H14A 110.5 . . ?
C10 C14 H14B 110.5 . . ?
C13 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
C12 C13 C14 107.6(2) . . ?
C12 C13 H13A 110.2 . . ?
C14 C13 H13A 110.2 . . ?
C12 C13 H13B 110.2 . . ?
C14 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?

_refine_diff_density_max         0.504
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_1_EtOAc
_database_code_depnum_ccdc_archive 'CCDC 1855338'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 O2'
_chemical_formula_weight         218.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_H-M_alt        'P 32 2 1'
_space_group_name_Hall           'P 32 2"'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'
'y, x, -z'

_cell_length_a                   14.3565(5)
_cell_length_b                   14.3565(5)
_cell_length_c                   6.5749(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1173.59(9)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2884
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      22.92

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.927
_exptl_crystal_F_000             354
_exptl_transmission_factor_min   0.986
_exptl_transmission_factor_max   0.993
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.061
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            8288
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.638
_diffrn_reflns_theta_max         23.378
_diffrn_reflns_theta_full        23.378
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1148
_reflns_number_gt                1071
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.996

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.000 0.000 -0.032 310.0 90.7
_platon_squeeze_details          
; ?
;
_computing_data_collection       'Bruker SMART APEX-II'
_computing_cell_refinement       'Bruker SMART APEX-II'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0825P)²+0.3376P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 441 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1148
_refine_ls_number_parameters     77
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1365
_refine_ls_wR_factor_gt          0.1347
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.6797(2) 0.27572(19) -0.0084(4) 0.0320(7) Uani 1 1 d . . . . .
H1 H 0.682(4) 0.308(4) -0.111(9) 0.064(15) Uiso 1 1 d . . . . .
C1 C 0.7299(3) 0.2113(3) -0.0187(5) 0.0309(9) Uani 1 1 d . . . . .
C2 C 0.8492(3) 0.2800(3) -0.0687(5) 0.0390(9) Uani 1 1 d . . . . .
H2A H 0.878261 0.234733 -0.119690 0.047 Uiso 1 1 calc R U . . .
H2B H 0.861038 0.334567 -0.173074 0.047 Uiso 1 1 calc R U . . .
C3 C 0.9024(4) 0.3336(4) 0.1312(6) 0.0578(13) Uani 1 1 d . . . . .
H3A H 0.971568 0.334800 0.147338 0.069 Uiso 1 1 calc R U . . .
H3B H 0.916680 0.408557 0.134470 0.069 Uiso 1 1 calc R U . . .
C4 C 0.8252(4) 0.2681(4) 0.3009(6) 0.0505(11) Uani 1 1 d . . . . .
H4B H 0.800348 0.311797 0.374725 0.061 Uiso 1 1 calc R U . . .
H4A H 0.860860 0.243645 0.398857 0.061 Uiso 1 1 calc R U . . .
C5 C 0.7307(3) 0.1720(3) 0.1990(5) 0.0365(10) Uani 1 1 d . . . . .
H5B H 0.662498 0.152197 0.270225 0.044 Uiso 1 1 calc R U . . .
H5A H 0.741361 0.109031 0.197403 0.044 Uiso 1 1 calc R U . . .
C6 C 0.6727(3) 0.1216(3) -0.1586(5) 0.0330(9) Uani 1 1 d . . . . .
C7 C 0.6308(3) 0.0444(3) -0.2710(5) 0.0351(9) Uani 1 1 d . . . . .


_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 1.430(4) . ?
O1 H1 0.81(6) . ?
C1 C6 1.456(5) . ?
C1 C2 1.525(5) . ?
C1 C5 1.541(5) . ?
C2 C3 1.522(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.522(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.523(6) . ?
C4 H4B 0.9900 . ?
C4 H4A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 H5A 0.9900 . ?
C6 C7 1.213(5) . ?
C7 C7 1.374(7) 4_554 ?

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 H1 117(3) . . ?
O1 C1 C6 111.0(3) . . ?
O1 C1 C2 111.0(3) . . ?
C6 C1 C2 113.0(3) . . ?
O1 C1 C5 106.9(3) . . ?
C6 C1 C5 111.6(3) . . ?
C2 C1 C5 103.0(3) . . ?
C3 C2 C1 105.0(3) . . ?
C3 C2 H2A 110.8 . . ?
C1 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.8 . . ?
C4 C3 C2 107.1(3) . . ?
C4 C3 H3A 110.3 . . ?
C2 C3 H3A 110.3 . . ?
C4 C3 H3B 110.3 . . ?
C2 C3 H3B 110.3 . . ?
H3A C3 H3B 108.5 . . ?
C3 C4 C5 106.3(3) . . ?
C3 C4 H4B 110.5 . . ?
C5 C4 H4B 110.5 . . ?
C3 C4 H4A 110.5 . . ?
C5 C4 H4A 110.5 . . ?
H4B C4 H4A 108.7 . . ?
C4 C5 C1 104.1(3) . . ?
C4 C5 H5B 110.9 . . ?
C1 C5 H5B 110.9 . . ?
C4 C5 H5A 110.9 . . ?
C1 C5 H5A 110.9 . . ?
H5B C5 H5A 109.0 . . ?
C7 C6 C1 174.8(4) . . ?
C6 C7 C7 177.6(3) . 4_554 ?

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_1_CCl4
_database_code_depnum_ccdc_archive 'CCDC 1855336'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 O2'
_chemical_formula_weight         218.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_H-M_alt        'P 32 2 1'
_space_group_name_Hall           'P 32 2"'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'
'y, x, -z'

_cell_length_a                   14.205(4)
_cell_length_b                   14.205(4)
_cell_length_c                   6.6233(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1157.4(7)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    732
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      16.98

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.940
_exptl_crystal_F_000             354
_exptl_transmission_factor_min   0.991
_exptl_transmission_factor_max   0.995
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.061
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            5148
_diffrn_reflns_av_unetI/netI     0.0819
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.312
_diffrn_reflns_theta_max         24.951
_diffrn_reflns_theta_full        24.951
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measured_fraction_theta_full 0.911
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_Laue_measured_fraction_full 0.911
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_point_group_measured_fraction_full 0.928
_reflns_number_total             1262
_reflns_number_gt                718
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_max     0.949
_reflns_Friedel_fraction_full    0.949

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.032 301 94 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?
_computing_data_collection       'Bruker SMART APEX-II'
_computing_cell_refinement       'Bruker SMART APEX-II'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0876P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 221 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1262
_refine_ls_number_parameters     77
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1262
_refine_ls_R_factor_gt           0.0718
_refine_ls_wR_factor_ref         0.1868
_refine_ls_wR_factor_gt          0.1622
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_restrained_S_all      0.943
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.2731(3) 0.6788(3) 0.0093(6) 0.0673(12) Uani 1 1 d . . . . .
H1 H 0.305(4) 0.680(4) 0.104(8) 0.042(15) Uiso 1 1 d . . . . .
C1 C 0.2105(5) 0.7311(5) 0.0146(8) 0.0678(16) Uani 1 1 d . . . . .
C2 C 0.2800(6) 0.8511(5) 0.0665(9) 0.0788(19) Uani 1 1 d . . . . .
H2A H 0.234663 0.880515 0.119187 0.095 Uiso 1 1 calc R U . . .
H2B H 0.335745 0.862667 0.168434 0.095 Uiso 1 1 calc R U . . .
C3 C 0.3303(9) 0.9022(8) -0.1241(13) 0.134(4) Uani 1 1 d . . . . .
H3B H 0.404064 0.911554 -0.133661 0.161 Uiso 1 1 calc R U . . .
H3A H 0.336556 0.974650 -0.134510 0.161 Uiso 1 1 calc R U . . .
C4 C 0.2601(10) 0.8301(9) -0.2886(17) 0.134(4) Uani 1 1 d . . . . .
H4A H 0.228801 0.867252 -0.366944 0.161 Uiso 1 1 calc R U . . .
H4B H 0.303596 0.812285 -0.381470 0.161 Uiso 1 1 calc R U . . .
C5 C 0.1720(5) 0.7294(5) -0.1975(9) 0.0761(18) Uani 1 1 d . . . . .
H5B H 0.161982 0.664403 -0.271208 0.091 Uiso 1 1 calc R U . . .
H5A H 0.102481 0.729772 -0.197847 0.091 Uiso 1 1 calc R U . . .
C6 C 0.1215(6) 0.6763(5) 0.1587(10) 0.0746(18) Uani 1 1 d . . . . .
C7 C 0.0424(5) 0.6367(6) 0.2709(10) 0.0768(18) Uani 1 1 d . . . . .


_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 1.417(8) . ?
O1 H1 0.77(5) . ?
C1 C6 1.460(10) . ?
C1 C5 1.503(8) . ?
C1 C2 1.522(10) . ?
C2 C3 1.453(11) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.487(14) . ?
C3 H3B 0.9900 . ?
C3 H3A 0.9900 . ?
C4 C5 1.478(12) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5B 0.9900 . ?
C5 H5A 0.9900 . ?
C6 C7 1.225(9) . ?
C7 C7 1.331(14) 5 ?

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 H1 119(3) . . ?
O1 C1 C6 109.8(5) . . ?
O1 C1 C5 106.7(5) . . ?
C6 C1 C5 113.1(5) . . ?
O1 C1 C2 111.6(5) . . ?
C6 C1 C2 110.7(5) . . ?
C5 C1 C2 104.9(5) . . ?
C3 C2 C1 104.2(6) . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C2 C3 C4 107.4(8) . . ?
C2 C3 H3B 110.2 . . ?
C4 C3 H3B 110.2 . . ?
C2 C3 H3A 110.2 . . ?
C4 C3 H3A 110.2 . . ?
H3B C3 H3A 108.5 . . ?
C5 C4 C3 108.6(8) . . ?
C5 C4 H4A 110.0 . . ?
C3 C4 H4A 110.0 . . ?
C5 C4 H4B 110.0 . . ?
C3 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
C4 C5 C1 103.9(7) . . ?
C4 C5 H5B 111.0 . . ?
C1 C5 H5B 111.0 . . ?
C4 C5 H5A 111.0 . . ?
C1 C5 H5A 111.0 . . ?
H5B C5 H5A 109.0 . . ?
C7 C6 C1 173.1(7) . . ?
C6 C7 C7 179.0(9) . 5 ?

_refine_diff_density_max         0.156
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_1_340K
_database_code_depnum_ccdc_archive 'CCDC 1855351'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
1,4-Bis(1-hydroxycyclopentyl)buta-1,3-diyne 
;
_chemical_name_common            ?
_chemical_melting_point          406K
_chemical_formula_moiety         'C14 H18 O2'
_chemical_formula_sum            'C14 H18 O2'
_chemical_formula_weight         218.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   6.9574(10)
_cell_length_b                   12.3167(17)
_cell_length_c                   14.993(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.665(2)
_cell_angle_gamma                90
_cell_volume                     1273.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    340(2)
_cell_measurement_reflns_used    1338
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      19.69

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9722
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      340(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7272
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.148
_diffrn_reflns_theta_max         27.469
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2768
_reflns_number_gt                1443
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART APEX-II'
_computing_cell_refinement       'Bruker SMART APEX-II'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1229P)²+0.1149P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2768
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1157
_refine_ls_R_factor_gt           0.0646
_refine_ls_wR_factor_ref         0.2429
_refine_ls_wR_factor_gt          0.1974
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.0420(3) 0.83394(14) 0.50413(11) 0.0914(7) Uani 1 1 d . . . . .
H1 H 0.050578 0.866032 0.456898 0.110 Uiso 1 1 calc R U . . .
C7 C -0.2530(4) 0.6593(2) 0.36782(18) 0.0803(8) Uani 1 1 d . . . . .
C9 C -0.5260(4) 0.5831(2) 0.25215(17) 0.0731(7) Uani 1 1 d . . . . .
C8 C -0.4025(4) 0.6208(2) 0.30509(18) 0.0762(7) Uani 1 1 d . . . . .
C2 C 0.0378(4) 0.6661(2) 0.57942(17) 0.0828(8) Uani 1 1 d . . . . .
H2A H -0.013673 0.592939 0.572269 0.099 Uiso 1 1 calc R U . . .
H2B H -0.040432 0.707474 0.616222 0.099 Uiso 1 1 calc R U . . .
C10 C -0.6806(4) 0.53445(19) 0.18799(15) 0.0684(7) Uani 1 1 d . . . . .
C1 C 0.0409(4) 0.72002(19) 0.48855(15) 0.0698(7) Uani 1 1 d . . . . .
C6 C -0.1238(4) 0.6895(2) 0.42206(18) 0.0766(7) Uani 1 1 d . . . . .
C5 C 0.2325(4) 0.6810(3) 0.4607(2) 0.0952(9) Uani 1 1 d . . . . .
H5A H 0.210674 0.619151 0.420539 0.114 Uiso 1 1 calc R U . . .
H5B H 0.292387 0.738460 0.429814 0.114 Uiso 1 1 calc R U . . .
O2 O -0.6026(3) 0.50386(15) 0.10877(12) 0.0957(7) Uani 1 1 d . . . . .
H2 H -0.559011 0.557660 0.086264 0.115 Uiso 1 1 calc R U . . .
C11 C -0.7663(5) 0.4322(2) 0.2238(2) 0.0917(9) Uani 1 1 d . . . . .
H11A H -0.689596 0.368922 0.212912 0.110 Uiso 1 1 calc R U . . .
H11B H -0.771985 0.438181 0.287860 0.110 Uiso 1 1 calc R U . . .
C3 C 0.2493(5) 0.6645(3) 0.6215(2) 0.1067(11) Uani 1 1 d . . . . .
H3A H 0.284581 0.732136 0.652520 0.128 Uiso 1 1 calc R U . . .
H3B H 0.273774 0.604949 0.663822 0.128 Uiso 1 1 calc R U . . .
C4 C 0.3591(6) 0.6498(4) 0.5442(3) 0.1307(14) Uani 1 1 d . . . . .
H4A H 0.398957 0.574679 0.540586 0.157 Uiso 1 1 calc R U . . .
H4B H 0.474398 0.694928 0.551953 0.157 Uiso 1 1 calc R U . . .
C12 C -0.9671(5) 0.4243(3) 0.1722(3) 0.1239(12) Uani 1 1 d . . . . .
H12A H -0.966983 0.375703 0.121290 0.149 Uiso 1 1 calc R U . . .
H12B H -1.057057 0.396218 0.210713 0.149 Uiso 1 1 calc R U . . .
C14 C -0.8553(4) 0.6080(2) 0.1655(2) 0.0940(9) Uani 1 1 d . . . . .
H14A H -0.874540 0.652454 0.217001 0.113 Uiso 1 1 calc R U . . .
H14B H -0.838093 0.655238 0.115454 0.113 Uiso 1 1 calc R U . . .
C13 C -1.0253(5) 0.5334(3) 0.1410(3) 0.1280(13) Uani 1 1 d . . . . .
H13A H -1.135043 0.557659 0.169441 0.154 Uiso 1 1 calc R U . . .
H13B H -1.062873 0.533204 0.076372 0.154 Uiso 1 1 calc R U . . .


_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 1.422(3) . ?
O1 H1 0.8200 . ?
C7 C6 1.189(4) . ?
C7 C8 1.389(4) . ?
C9 C8 1.184(3) . ?
C9 C10 1.471(4) . ?
C2 C1 1.519(3) . ?
C2 C3 1.522(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C10 O2 1.421(3) . ?
C10 C14 1.517(4) . ?
C10 C11 1.522(4) . ?
C1 C6 1.464(4) . ?
C1 C5 1.527(4) . ?
C5 C4 1.482(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
O2 H2 0.8200 . ?
C11 C12 1.507(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C3 C4 1.481(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C12 C13 1.462(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 C13 1.504(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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 H1 109.5 . . ?
C6 C7 C8 178.3(3) . . ?
C8 C9 C10 178.7(3) . . ?
C9 C8 C7 176.8(3) . . ?
C1 C2 C3 104.4(2) . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
O2 C10 C9 109.1(2) . . ?
O2 C10 C14 110.9(2) . . ?
C9 C10 C14 113.3(2) . . ?
O2 C10 C11 106.6(2) . . ?
C9 C10 C11 113.2(2) . . ?
C14 C10 C11 103.4(2) . . ?
O1 C1 C6 110.6(2) . . ?
O1 C1 C2 106.55(19) . . ?
C6 C1 C2 113.3(2) . . ?
O1 C1 C5 111.7(2) . . ?
C6 C1 C5 111.4(2) . . ?
C2 C1 C5 103.0(2) . . ?
C7 C6 C1 176.4(3) . . ?
C4 C5 C1 107.0(3) . . ?
C4 C5 H5A 110.3 . . ?
C1 C5 H5A 110.3 . . ?
C4 C5 H5B 110.3 . . ?
C1 C5 H5B 110.3 . . ?
H5A C5 H5B 108.6 . . ?
C10 O2 H2 109.5 . . ?
C12 C11 C10 104.6(2) . . ?
C12 C11 H11A 110.8 . . ?
C10 C11 H11A 110.8 . . ?
C12 C11 H11B 110.8 . . ?
C10 C11 H11B 110.8 . . ?
H11A C11 H11B 108.9 . . ?
C4 C3 C2 104.4(3) . . ?
C4 C3 H3A 110.9 . . ?
C2 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
C2 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
C3 C4 C5 108.6(3) . . ?
C3 C4 H4A 110.0 . . ?
C5 C4 H4A 110.0 . . ?
C3 C4 H4B 110.0 . . ?
C5 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
C13 C12 C11 107.6(3) . . ?
C13 C12 H12A 110.2 . . ?
C11 C12 H12A 110.2 . . ?
C13 C12 H12B 110.2 . . ?
C11 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C13 C14 C10 105.7(3) . . ?
C13 C14 H14A 110.6 . . ?
C10 C14 H14A 110.6 . . ?
C13 C14 H14B 110.6 . . ?
C10 C14 H14B 110.6 . . ?
H14A C14 H14B 108.7 . . ?
C12 C13 C14 108.0(3) . . ?
C12 C13 H13A 110.1 . . ?
C14 C13 H13A 110.1 . . ?
C12 C13 H13B 110.1 . . ?
C14 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_1_120K
_database_code_depnum_ccdc_archive 'CCDC 1855340'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
; 
1,4-Bis(1-hydroxycyclopentyl)buta-1,3-diyne 
;
_chemical_name_common            ?
_chemical_melting_point          406K
_chemical_formula_moiety         'C14 H18 O2'
_chemical_formula_sum            'C14 H18 O2'
_chemical_formula_weight         218.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   7.1268(7)
_cell_length_b                   11.9819(11)
_cell_length_c                   14.4375(13)
_cell_angle_alpha                90
_cell_angle_beta                 97.4320(10)
_cell_angle_gamma                90
_cell_volume                     1222.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2460
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      27.26

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9711
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            6953
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.216
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2646
_reflns_number_gt                2122
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART APEX-II'
_computing_cell_refinement       'Bruker SMART APEX-II'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0591P)²+1.0722P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2646
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1564
_refine_ls_wR_factor_gt          0.1452
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.0709(2) 0.83244(11) 0.51043(10) 0.0327(4) Uani 1 1 d . . . . .
H1 H 0.078639 0.864446 0.459298 0.039 Uiso 1 1 calc R U . . .
C7 C -0.2478(3) 0.65755(16) 0.37570(14) 0.0301(4) Uani 1 1 d . . . . .
C9 C -0.5219(3) 0.58364(15) 0.25747(13) 0.0282(4) Uani 1 1 d . . . . .
C8 C -0.3967(3) 0.62056(16) 0.31217(13) 0.0293(4) Uani 1 1 d . . . . .
C2 C 0.0579(3) 0.66169(16) 0.59265(13) 0.0295(4) Uani 1 1 d . . . . .
H2A H -0.024288 0.703506 0.630763 0.035 Uiso 1 1 calc R U . . .
H2B H 0.015981 0.582886 0.587918 0.035 Uiso 1 1 calc R U . . .
C10 C -0.6730(3) 0.53497(15) 0.19024(12) 0.0270(4) Uani 1 1 d . . . . .
C1 C 0.0544(3) 0.71420(15) 0.49564(13) 0.0254(4) Uani 1 1 d . . . . .
C6 C -0.1153(3) 0.68628(16) 0.43051(14) 0.0300(4) Uani 1 1 d . . . . .
C5 C 0.2351(3) 0.66648(17) 0.46256(14) 0.0310(4) Uani 1 1 d . . . . .
H5A H 0.208126 0.594397 0.430037 0.037 Uiso 1 1 calc R U . . .
H5B H 0.286552 0.719062 0.419319 0.037 Uiso 1 1 calc R U . . .
O2 O -0.5948(3) 0.50416(14) 0.10773(11) 0.0577(6) Uani 1 1 d . . . . .
H2 H -0.550415 0.561028 0.084360 0.069 Uiso 1 1 calc R U . . .
C11 C -0.7574(3) 0.42784(16) 0.22563(14) 0.0329(5) Uani 1 1 d . . . . .
H11A H -0.677949 0.362332 0.215357 0.040 Uiso 1 1 calc R U . . .
H11B H -0.769326 0.433490 0.293025 0.040 Uiso 1 1 calc R U . . .
C3 C 0.2658(3) 0.67028(17) 0.63440(14) 0.0329(5) Uani 1 1 d . . . . .
H3A H 0.297768 0.613028 0.683348 0.039 Uiso 1 1 calc R U . . .
H3B H 0.294223 0.745021 0.661922 0.039 Uiso 1 1 calc R U . . .
C4 C 0.3759(3) 0.6503(2) 0.55133(15) 0.0396(5) Uani 1 1 d . . . . .
H4A H 0.481673 0.704057 0.552681 0.048 Uiso 1 1 calc R U . . .
H4B H 0.428368 0.573702 0.553591 0.048 Uiso 1 1 calc R U . . .
C12 C -0.9522(3) 0.4189(2) 0.16735(17) 0.0452(6) Uani 1 1 d . . . . .
H12A H -0.943350 0.376577 0.109190 0.054 Uiso 1 1 calc R U . . .
H12B H -1.042330 0.380307 0.203137 0.054 Uiso 1 1 calc R U . . .
C14 C -0.8443(3) 0.61163(18) 0.16817(19) 0.0483(6) Uani 1 1 d . . . . .
H14A H -0.828830 0.660226 0.114219 0.058 Uiso 1 1 calc R U . . .
H14B H -0.859864 0.659387 0.222617 0.058 Uiso 1 1 calc R U . . .
C13 C -1.0157(4) 0.5351(2) 0.1453(3) 0.0760(10) Uani 1 1 d . . . . .
H13A H -1.116736 0.556209 0.182982 0.091 Uiso 1 1 calc R U . . .
H13B H -1.066471 0.541499 0.078346 0.091 Uiso 1 1 calc R U . . .


_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 1.435(2) . ?
O1 H1 0.8400 . ?
C7 C6 1.201(3) . ?
C7 C8 1.383(3) . ?
C9 C8 1.197(3) . ?
C9 C10 1.474(3) . ?
C2 C3 1.530(3) . ?
C2 C1 1.533(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C10 O2 1.428(2) . ?
C10 C14 1.528(3) . ?
C10 C11 1.533(3) . ?
C1 C6 1.471(3) . ?
C1 C5 1.540(2) . ?
C5 C4 1.534(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
O2 H2 0.8400 . ?
C11 C12 1.531(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C3 C4 1.534(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C12 C13 1.485(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 C13 1.529(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

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 H1 109.5 . . ?
C6 C7 C8 177.8(2) . . ?
C8 C9 C10 178.3(2) . . ?
C9 C8 C7 176.9(2) . . ?
C3 C2 C1 103.46(15) . . ?
C3 C2 H2A 111.1 . . ?
C1 C2 H2A 111.1 . . ?
C3 C2 H2B 111.1 . . ?
C1 C2 H2B 111.1 . . ?
H2A C2 H2B 109.0 . . ?
O2 C10 C9 108.72(16) . . ?
O2 C10 C14 111.67(18) . . ?
C9 C10 C14 113.30(16) . . ?
O2 C10 C11 105.90(15) . . ?
C9 C10 C11 113.36(16) . . ?
C14 C10 C11 103.64(17) . . ?
O1 C1 C6 111.35(15) . . ?
O1 C1 C2 106.14(14) . . ?
C6 C1 C2 113.92(16) . . ?
O1 C1 C5 110.92(15) . . ?
C6 C1 C5 111.62(15) . . ?
C2 C1 C5 102.46(15) . . ?
C7 C6 C1 175.8(2) . . ?
C4 C5 C1 105.68(15) . . ?
C4 C5 H5A 110.6 . . ?
C1 C5 H5A 110.6 . . ?
C4 C5 H5B 110.6 . . ?
C1 C5 H5B 110.6 . . ?
H5A C5 H5B 108.7 . . ?
C10 O2 H2 109.5 . . ?
C12 C11 C10 104.00(16) . . ?
C12 C11 H11A 111.0 . . ?
C10 C11 H11A 111.0 . . ?
C12 C11 H11B 111.0 . . ?
C10 C11 H11B 111.0 . . ?
H11A C11 H11B 109.0 . . ?
C2 C3 C4 104.40(16) . . ?
C2 C3 H3A 110.9 . . ?
C4 C3 H3A 110.9 . . ?
C2 C3 H3B 110.9 . . ?
C4 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
C5 C4 C3 106.75(16) . . ?
C5 C4 H4A 110.4 . . ?
C3 C4 H4A 110.4 . . ?
C5 C4 H4B 110.4 . . ?
C3 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
C13 C12 C11 106.40(19) . . ?
C13 C12 H12A 110.4 . . ?
C11 C12 H12A 110.4 . . ?
C13 C12 H12B 110.4 . . ?
C11 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
C10 C14 C13 106.18(19) . . ?
C10 C14 H14A 110.5 . . ?
C13 C14 H14A 110.5 . . ?
C10 C14 H14B 110.5 . . ?
C13 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
C12 C13 C14 107.6(2) . . ?
C12 C13 H13A 110.2 . . ?
C14 C13 H13A 110.2 . . ?
C12 C13 H13B 110.2 . . ?
C14 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?

_refine_diff_density_max         0.668
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_1_300K
_database_code_depnum_ccdc_archive 'CCDC 1855349'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
1,4-Bis(1-hydroxycyclopentyl)buta-1,3-diyne 
;
_chemical_name_common            ?
_chemical_melting_point          406K
_chemical_formula_moiety         'C14 H18 O2'
_chemical_formula_sum            'C14 H18 O2'
_chemical_formula_weight         218.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   6.9814(12)
_cell_length_b                   12.218(2)
_cell_length_c                   14.914(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.532(3)
_cell_angle_gamma                90
_cell_volume                     1261.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    1533
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      21.92

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9720
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            7189
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.162
_diffrn_reflns_theta_max         27.438
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2733
_reflns_number_gt                1623
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART APEX-II'
_computing_cell_refinement       'Bruker SMART APEX-II'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_refine_special_details          ?
_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+0.1550P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2733
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_ref         0.2077
_refine_ls_wR_factor_gt          0.1767
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.0467(3) 0.83312(12) 0.50526(10) 0.0761(5) Uani 1 1 d . . . . .
H1 H 0.055212 0.865482 0.457779 0.091 Uiso 1 1 calc R U . . .
C7 C -0.2531(4) 0.65859(18) 0.36838(16) 0.0678(6) Uani 1 1 d . . . . .
C9 C -0.5267(3) 0.58344(18) 0.25201(15) 0.0629(6) Uani 1 1 d . . . . .
C8 C -0.4013(4) 0.62072(18) 0.30552(16) 0.0650(6) Uani 1 1 d . . . . .
C2 C 0.0406(4) 0.66382(19) 0.58120(15) 0.0681(6) Uani 1 1 d . . . . .
H2A H -0.039146 0.704932 0.617872 0.082 Uiso 1 1 calc R U . . .
H2B H -0.007902 0.589475 0.574457 0.082 Uiso 1 1 calc R U . . .
C10 C -0.6807(3) 0.53487(16) 0.18785(14) 0.0583(6) Uani 1 1 d . . . . .
C1 C 0.0432(3) 0.71790(16) 0.48932(14) 0.0587(6) Uani 1 1 d . . . . .
C6 C -0.1226(4) 0.68823(18) 0.42284(16) 0.0652(6) Uani 1 1 d . . . . .
C5 C 0.2333(4) 0.6775(2) 0.46049(17) 0.0783(7) Uani 1 1 d . . . . .
H5A H 0.210906 0.613763 0.421763 0.094 Uiso 1 1 calc R U . . .
H5B H 0.291645 0.734331 0.427619 0.094 Uiso 1 1 calc R U . . .
O2 O -0.6031(3) 0.50386(14) 0.10786(11) 0.0848(6) Uani 1 1 d . . . . .
H2 H -0.559417 0.558034 0.085198 0.102 Uiso 1 1 calc R U . . .
C11 C -0.7662(4) 0.4316(2) 0.22329(17) 0.0766(7) Uani 1 1 d . . . . .
H11A H -0.688780 0.368086 0.212805 0.092 Uiso 1 1 calc R U . . .
H11B H -0.773735 0.437619 0.287585 0.092 Uiso 1 1 calc R U . . .
C3 C 0.2511(4) 0.6651(2) 0.62312(18) 0.0851(8) Uani 1 1 d . . . . .
H3A H 0.283950 0.734518 0.652831 0.102 Uiso 1 1 calc R U . . .
H3B H 0.277112 0.606647 0.666997 0.102 Uiso 1 1 calc R U . . .
C4 C 0.3625(5) 0.6489(3) 0.5455(2) 0.1068(10) Uani 1 1 d . . . . .
H4A H 0.404362 0.573327 0.543249 0.128 Uiso 1 1 calc R U . . .
H4B H 0.476016 0.695449 0.552217 0.128 Uiso 1 1 calc R U . . .
C12 C -0.9659(4) 0.4231(3) 0.1703(2) 0.1028(10) Uani 1 1 d . . . . .
H12A H -0.963430 0.375707 0.118310 0.123 Uiso 1 1 calc R U . . .
H12B H -1.056039 0.392944 0.208045 0.123 Uiso 1 1 calc R U . . .
C14 C -0.8544(4) 0.6097(2) 0.1660(2) 0.0804(7) Uani 1 1 d . . . . .
H14A H -0.873377 0.654074 0.218008 0.096 Uiso 1 1 calc R U . . .
H14B H -0.837119 0.657747 0.115869 0.096 Uiso 1 1 calc R U . . .
C13 C -1.0246(5) 0.5341(3) 0.1410(3) 0.1137(11) Uani 1 1 d . . . . .
H13A H -1.133275 0.557668 0.170579 0.136 Uiso 1 1 calc R U . . .
H13B H -1.063388 0.535433 0.076136 0.136 Uiso 1 1 calc R U . . .


_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 1.427(2) . ?
O1 H1 0.8200 . ?
C7 C6 1.194(3) . ?
C7 C8 1.382(4) . ?
C9 C8 1.195(3) . ?
C9 C10 1.468(3) . ?
C2 C3 1.520(4) . ?
C2 C1 1.524(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C10 O2 1.425(3) . ?
C10 C14 1.520(3) . ?
C10 C11 1.520(3) . ?
C1 C6 1.467(3) . ?
C1 C5 1.529(3) . ?
C5 C4 1.498(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
O2 H2 0.8200 . ?
C11 C12 1.513(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C3 C4 1.490(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C12 C13 1.467(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 C13 1.512(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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 H1 109.5 . . ?
C6 C7 C8 178.0(2) . . ?
C8 C9 C10 178.4(2) . . ?
C9 C8 C7 177.1(2) . . ?
C3 C2 C1 103.9(2) . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
O2 C10 C9 109.09(18) . . ?
O2 C10 C14 111.13(19) . . ?
C9 C10 C14 113.11(18) . . ?
O2 C10 C11 106.27(17) . . ?
C9 C10 C11 113.34(18) . . ?
C14 C10 C11 103.6(2) . . ?
O1 C1 C6 110.54(17) . . ?
O1 C1 C2 106.25(17) . . ?
C6 C1 C2 113.53(18) . . ?
O1 C1 C5 111.63(19) . . ?
C6 C1 C5 111.52(18) . . ?
C2 C1 C5 103.06(19) . . ?
C7 C6 C1 176.4(2) . . ?
C4 C5 C1 106.6(2) . . ?
C4 C5 H5A 110.4 . . ?
C1 C5 H5A 110.4 . . ?
C4 C5 H5B 110.4 . . ?
C1 C5 H5B 110.4 . . ?
H5A C5 H5B 108.6 . . ?
C10 O2 H2 109.5 . . ?
C12 C11 C10 104.6(2) . . ?
C12 C11 H11A 110.8 . . ?
C10 C11 H11A 110.8 . . ?
C12 C11 H11B 110.8 . . ?
C10 C11 H11B 110.8 . . ?
H11A C11 H11B 108.9 . . ?
C4 C3 C2 104.7(2) . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C3 C4 C5 108.0(2) . . ?
C3 C4 H4A 110.1 . . ?
C5 C4 H4A 110.1 . . ?
C3 C4 H4B 110.1 . . ?
C5 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
C13 C12 C11 107.1(2) . . ?
C13 C12 H12A 110.3 . . ?
C11 C12 H12A 110.3 . . ?
C13 C12 H12B 110.3 . . ?
C11 C12 H12B 110.3 . . ?
H12A C12 H12B 108.5 . . ?
C13 C14 C10 105.3(2) . . ?
C13 C14 H14A 110.7 . . ?
C10 C14 H14A 110.7 . . ?
C13 C14 H14B 110.7 . . ?
C10 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
C12 C13 C14 108.2(3) . . ?
C12 C13 H13A 110.1 . . ?
C14 C13 H13A 110.1 . . ?
C12 C13 H13B 110.1 . . ?
C14 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_1_100K
_database_code_depnum_ccdc_archive 'CCDC 1855339'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
; 
1,4-Bis(1-hydroxycyclopentyl)buta-1,3-diyne 
;
_chemical_name_common            ?
_chemical_melting_point          406K
_chemical_formula_moiety         'C14 H18 O2'
_chemical_formula_sum            'C14 H18 O2'
_chemical_formula_weight         218.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   7.1352(6)
_cell_length_b                   11.9641(10)
_cell_length_c                   14.4049(12)
_cell_angle_alpha                90
_cell_angle_beta                 97.3660(10)
_cell_angle_gamma                90
_cell_volume                     1219.54(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2810
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      26.84

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9710
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            6909
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.220
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2641
_reflns_number_gt                2207
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART APEX-II'
_computing_cell_refinement       'Bruker SMART APEX-II'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0656P)²+1.3546P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2641
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0666
_refine_ls_wR_factor_ref         0.1682
_refine_ls_wR_factor_gt          0.1593
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.0737(2) 0.83263(11) 0.51097(10) 0.0296(4) Uani 1 1 d . . . . .
H1 H 0.081402 0.864290 0.459548 0.036 Uiso 1 1 calc R U . . .
C7 C -0.2465(3) 0.65746(17) 0.37716(14) 0.0272(4) Uani 1 1 d . . . . .
C9 C -0.5207(3) 0.58353(16) 0.25847(14) 0.0255(4) Uani 1 1 d . . . . .
C8 C -0.3952(3) 0.62059(16) 0.31358(14) 0.0264(4) Uani 1 1 d . . . . .
C2 C 0.0601(3) 0.66210(16) 0.59426(14) 0.0265(4) Uani 1 1 d . . . . .
H2A H -0.021818 0.704144 0.632466 0.032 Uiso 1 1 calc R U . . .
H2B H 0.018602 0.583108 0.589963 0.032 Uiso 1 1 calc R U . . .
C10 C -0.6706(3) 0.53463(16) 0.19086(13) 0.0244(4) Uani 1 1 d . . . . .
C1 C 0.0561(3) 0.71417(15) 0.49669(13) 0.0230(4) Uani 1 1 d . . . . .
C6 C -0.1143(3) 0.68635(17) 0.43189(14) 0.0264(4) Uani 1 1 d . . . . .
C5 C 0.2365(3) 0.66604(17) 0.46317(14) 0.0278(5) Uani 1 1 d . . . . .
H5A H 0.209414 0.593431 0.431283 0.033 Uiso 1 1 calc R U . . .
H5B H 0.286975 0.718205 0.419157 0.033 Uiso 1 1 calc R U . . .
O2 O -0.5903(3) 0.50335(15) 0.10883(12) 0.0553(6) Uani 1 1 d . . . . .
H2 H -0.545309 0.560168 0.085511 0.066 Uiso 1 1 calc R U . . .
C11 C -0.7557(3) 0.42743(17) 0.22623(15) 0.0294(5) Uani 1 1 d . . . . .
H11A H -0.767886 0.433107 0.293763 0.035 Uiso 1 1 calc R U . . .
H11B H -0.676643 0.361688 0.215965 0.035 Uiso 1 1 calc R U . . .
C3 C 0.2682(3) 0.67124(17) 0.63560(14) 0.0287(5) Uani 1 1 d . . . . .
H3A H 0.300777 0.614185 0.684811 0.034 Uiso 1 1 calc R U . . .
H3B H 0.296320 0.746260 0.662890 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3782(3) 0.6510(2) 0.55194(15) 0.0345(5) Uani 1 1 d . . . . .
H4A H 0.483101 0.705316 0.552707 0.041 Uiso 1 1 calc R U . . .
H4B H 0.431657 0.574540 0.554509 0.041 Uiso 1 1 calc R U . . .
C12 C -0.9506(3) 0.4187(2) 0.16766(18) 0.0414(6) Uani 1 1 d . . . . .
H12A H -0.941838 0.376224 0.109403 0.050 Uiso 1 1 calc R U . . .
H12B H -1.041015 0.380308 0.203527 0.050 Uiso 1 1 calc R U . . .
C14 C -0.8412(4) 0.61161(19) 0.1680(2) 0.0471(7) Uani 1 1 d . . . . .
H14A H -0.825345 0.659569 0.113599 0.057 Uiso 1 1 calc R U . . .
H14B H -0.856814 0.660116 0.222213 0.057 Uiso 1 1 calc R U . . .
C13 C -1.0127(4) 0.5347(2) 0.1456(3) 0.0757(12) Uani 1 1 d . . . . .
H13A H -1.113268 0.556206 0.183596 0.091 Uiso 1 1 calc R U . . .
H13B H -1.063804 0.541071 0.078641 0.091 Uiso 1 1 calc R U . . .


_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 1.435(2) . ?
O1 H1 0.8400 . ?
C7 C6 1.200(3) . ?
C7 C8 1.382(3) . ?
C9 C8 1.203(3) . ?
C9 C10 1.472(3) . ?
C2 C3 1.531(3) . ?
C2 C1 1.534(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C10 O2 1.428(2) . ?
C10 C14 1.528(3) . ?
C10 C11 1.534(3) . ?
C1 C6 1.473(3) . ?
C1 C5 1.543(3) . ?
C5 C4 1.536(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
O2 H2 0.8400 . ?
C11 C12 1.535(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C3 C4 1.539(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C12 C13 1.479(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 C13 1.532(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

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 H1 109.5 . . ?
C6 C7 C8 177.9(2) . . ?
C8 C9 C10 178.0(2) . . ?
C9 C8 C7 176.9(2) . . ?
C3 C2 C1 103.33(16) . . ?
C3 C2 H2A 111.1 . . ?
C1 C2 H2A 111.1 . . ?
C3 C2 H2B 111.1 . . ?
C1 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
O2 C10 C9 108.47(17) . . ?
O2 C10 C14 111.92(19) . . ?
C9 C10 C14 113.19(17) . . ?
O2 C10 C11 105.89(16) . . ?
C9 C10 C11 113.41(16) . . ?
C14 C10 C11 103.72(18) . . ?
O1 C1 C6 111.35(16) . . ?
O1 C1 C2 106.17(15) . . ?
C6 C1 C2 113.94(16) . . ?
O1 C1 C5 110.62(16) . . ?
C6 C1 C5 111.79(16) . . ?
C2 C1 C5 102.52(16) . . ?
C7 C6 C1 175.5(2) . . ?
C4 C5 C1 105.66(16) . . ?
C4 C5 H5A 110.6 . . ?
C1 C5 H5A 110.6 . . ?
C4 C5 H5B 110.6 . . ?
C1 C5 H5B 110.6 . . ?
H5A C5 H5B 108.7 . . ?
C10 O2 H2 109.5 . . ?
C10 C11 C12 104.08(17) . . ?
C10 C11 H11A 110.9 . . ?
C12 C11 H11A 110.9 . . ?
C10 C11 H11B 110.9 . . ?
C12 C11 H11B 110.9 . . ?
H11A C11 H11B 109.0 . . ?
C2 C3 C4 104.52(16) . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
C4 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C5 C4 C3 106.61(17) . . ?
C5 C4 H4A 110.4 . . ?
C3 C4 H4A 110.4 . . ?
C5 C4 H4B 110.4 . . ?
C3 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
C13 C12 C11 106.2(2) . . ?
C13 C12 H12A 110.5 . . ?
C11 C12 H12A 110.5 . . ?
C13 C12 H12B 110.5 . . ?
C11 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C10 C14 C13 106.03(19) . . ?
C10 C14 H14A 110.5 . . ?
C13 C14 H14A 110.5 . . ?
C10 C14 H14B 110.5 . . ?
C13 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
C12 C13 C14 108.0(2) . . ?
C12 C13 H13A 110.1 . . ?
C14 C13 H13A 110.1 . . ?
C12 C13 H13B 110.1 . . ?
C14 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?

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
O1 H1 O2 0.84 1.94 2.686(2) 147.7 2_455 yes
O2 H2 O1 0.84 1.94 2.762(2) 167.0 4_575 yes

_refine_diff_density_max         0.789
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_1_320K
_database_code_depnum_ccdc_archive 'CCDC 1855350'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
1,4-Bis(1-hydroxycyclopentyl)buta-1,3-diyne 
;
_chemical_name_common            ?
_chemical_melting_point          406K
_chemical_formula_moiety         'C14 H18 O2'
_chemical_formula_sum            'C14 H18 O2'
_chemical_formula_weight         218.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   6.9670(14)
_cell_length_b                   12.261(2)
_cell_length_c                   14.960(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.580(3)
_cell_angle_gamma                90
_cell_volume                     1266.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    320(2)
_cell_measurement_reflns_used    1421
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      21.84

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9721
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      320(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            7217
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.155
_diffrn_reflns_theta_max         27.474
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2746
_reflns_number_gt                1502
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART APEX-II'
_computing_cell_refinement       'Bruker SMART APEX-II'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1194P)²+0.0549P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2746
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.2282
_refine_ls_wR_factor_gt          0.1915
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.0448(3) 0.83340(13) 0.50466(10) 0.0839(6) Uani 1 1 d . . . . .
H1 H 0.053468 0.865690 0.457363 0.101 Uiso 1 1 calc R U . . .
C7 C -0.2533(4) 0.65871(19) 0.36809(17) 0.0744(7) Uani 1 1 d . . . . .
C9 C -0.5267(4) 0.58344(19) 0.25216(15) 0.0685(6) Uani 1 1 d . . . . .
C8 C -0.4022(4) 0.62061(19) 0.30546(17) 0.0713(7) Uani 1 1 d . . . . .
C2 C 0.0391(4) 0.6649(2) 0.58028(16) 0.0752(7) Uani 1 1 d . . . . .
H2A H -0.039961 0.706259 0.616911 0.090 Uiso 1 1 calc R U . . .
H2B H -0.010873 0.591098 0.573418 0.090 Uiso 1 1 calc R U . . .
C10 C -0.6811(3) 0.53451(17) 0.18776(14) 0.0636(6) Uani 1 1 d . . . . .
C1 C 0.0422(3) 0.71879(17) 0.48881(14) 0.0642(6) Uani 1 1 d . . . . .
C6 C -0.1231(4) 0.68878(19) 0.42237(16) 0.0712(6) Uani 1 1 d . . . . .
C5 C 0.2330(4) 0.6792(3) 0.46067(18) 0.0868(8) Uani 1 1 d . . . . .
H5A H 0.211102 0.616232 0.421380 0.104 Uiso 1 1 calc R U . . .
H5B H 0.291982 0.736329 0.428682 0.104 Uiso 1 1 calc R U . . .
O2 O -0.6029(3) 0.50395(14) 0.10831(12) 0.0900(6) Uani 1 1 d . . . . .
H2 H -0.559422 0.558063 0.085793 0.108 Uiso 1 1 calc R U . . .
C11 C -0.7657(4) 0.4321(2) 0.22377(18) 0.0838(8) Uani 1 1 d . . . . .
H11A H -0.688394 0.368715 0.213326 0.101 Uiso 1 1 calc R U . . .
H11B H -0.772430 0.438500 0.287907 0.101 Uiso 1 1 calc R U . . .
C3 C 0.2500(4) 0.6648(2) 0.62222(19) 0.0956(9) Uani 1 1 d . . . . .
H3A H 0.283886 0.733341 0.652694 0.115 Uiso 1 1 calc R U . . .
H3B H 0.275313 0.605714 0.665264 0.115 Uiso 1 1 calc R U . . .
C4 C 0.3610(5) 0.6496(3) 0.5450(2) 0.1210(12) Uani 1 1 d . . . . .
H4A H 0.402529 0.574323 0.542123 0.145 Uiso 1 1 calc R U . . .
H4B H 0.475088 0.695773 0.552236 0.145 Uiso 1 1 calc R U . . .
C12 C -0.9663(5) 0.4238(3) 0.1713(3) 0.1142(11) Uani 1 1 d . . . . .
H12A H -0.964757 0.375713 0.119893 0.137 Uiso 1 1 calc R U . . .
H12B H -1.056563 0.394722 0.209324 0.137 Uiso 1 1 calc R U . . .
C14 C -0.8546(4) 0.6091(2) 0.1656(2) 0.0874(8) Uani 1 1 d . . . . .
H14A H -0.873648 0.653573 0.217281 0.105 Uiso 1 1 calc R U . . .
H14B H -0.837029 0.656644 0.115489 0.105 Uiso 1 1 calc R U . . .
C13 C -1.0248(5) 0.5339(3) 0.1409(3) 0.1202(12) Uani 1 1 d . . . . .
H13A H -1.134118 0.557931 0.169771 0.144 Uiso 1 1 calc R U . . .
H13B H -1.062827 0.534395 0.076119 0.144 Uiso 1 1 calc R U . . .


_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 1.425(3) . ?
O1 H1 0.8200 . ?
C7 C6 1.193(3) . ?
C7 C8 1.384(4) . ?
C9 C8 1.189(3) . ?
C9 C10 1.474(3) . ?
C2 C3 1.520(4) . ?
C2 C1 1.522(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C10 O2 1.422(3) . ?
C10 C11 1.516(3) . ?
C10 C14 1.517(3) . ?
C1 C6 1.466(3) . ?
C1 C5 1.525(3) . ?
C5 C4 1.491(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
O2 H2 0.8200 . ?
C11 C12 1.514(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C3 C4 1.484(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C12 C13 1.465(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 C13 1.508(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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 H1 109.5 . . ?
C6 C7 C8 178.3(3) . . ?
C8 C9 C10 178.3(2) . . ?
C9 C8 C7 177.1(3) . . ?
C3 C2 C1 104.1(2) . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 109.0 . . ?
O2 C10 C9 109.04(19) . . ?
O2 C10 C11 106.78(18) . . ?
C9 C10 C11 112.91(19) . . ?
O2 C10 C14 110.99(19) . . ?
C9 C10 C14 112.94(19) . . ?
C11 C10 C14 104.0(2) . . ?
O1 C1 C6 110.61(18) . . ?
O1 C1 C2 106.25(18) . . ?
C6 C1 C2 113.4(2) . . ?
O1 C1 C5 111.6(2) . . ?
C6 C1 C5 111.6(2) . . ?
C2 C1 C5 103.1(2) . . ?
C7 C6 C1 176.4(2) . . ?
C4 C5 C1 106.9(2) . . ?
C4 C5 H5A 110.4 . . ?
C1 C5 H5A 110.4 . . ?
C4 C5 H5B 110.4 . . ?
C1 C5 H5B 110.4 . . ?
H5A C5 H5B 108.6 . . ?
C10 O2 H2 109.5 . . ?
C12 C11 C10 104.3(2) . . ?
C12 C11 H11A 110.9 . . ?
C10 C11 H11A 110.9 . . ?
C12 C11 H11B 110.9 . . ?
C10 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
C4 C3 C2 104.7(2) . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C3 C4 C5 108.2(3) . . ?
C3 C4 H4A 110.0 . . ?
C5 C4 H4A 110.0 . . ?
C3 C4 H4B 110.0 . . ?
C5 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
C13 C12 C11 107.4(3) . . ?
C13 C12 H12A 110.2 . . ?
C11 C12 H12A 110.2 . . ?
C13 C12 H12B 110.2 . . ?
C11 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C13 C14 C10 105.3(2) . . ?
C13 C14 H14A 110.7 . . ?
C10 C14 H14A 110.7 . . ?
C13 C14 H14B 110.7 . . ?
C10 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
C12 C13 C14 108.0(3) . . ?
C12 C13 H13A 110.1 . . ?
C14 C13 H13A 110.1 . . ?
C12 C13 H13B 110.1 . . ?
C14 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_1_160K
_database_code_depnum_ccdc_archive 'CCDC 1855342'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
; 
1,4-Bis(1-hydroxycyclopentyl)buta-1,3-diyne 
;
_chemical_name_common            ?
_chemical_melting_point          406K
_chemical_formula_moiety         'C14 H18 O2'
_chemical_formula_sum            'C14 H18 O2'
_chemical_formula_weight         218.28


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   7.1120(6)
_cell_length_b                   12.0123(11)
_cell_length_c                   14.5000(13)
_cell_angle_alpha                90
_cell_angle_beta                 97.5580(10)
_cell_angle_gamma                90
_cell_volume                     1227.99(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    2268
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      27.18

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9712
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            6977
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.210
_diffrn_reflns_theta_max         27.432
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2652
_reflns_number_gt                2061
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART APEX-II'
_computing_cell_refinement       'Bruker SMART APEX-II'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0722P)²+0.5934P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2652
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1608
_refine_ls_wR_factor_gt          0.1457
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.0658(2) 0.83196(10) 0.50793(9) 0.0418(4) Uani 1 1 d . . . . .
H1 H 0.074226 0.863799 0.457055 0.050 Uiso 1 1 calc R U . . .
C7 C -0.2503(3) 0.65693(15) 0.37295(13) 0.0374(4) Uani 1 1 d . . . . .
C9 C -0.5254(3) 0.58367(14) 0.25492(13) 0.0344(4) Uani 1 1 d . . . . .
C8 C -0.3995(3) 0.62029(15) 0.30955(13) 0.0360(4) Uani 1 1 d . . . . .
C2 C 0.0529(3) 0.66173(15) 0.58976(13) 0.0364(4) Uani 1 1 d . . . . .
H2A H -0.028984 0.703904 0.627548 0.044 Uiso 1 1 calc R U . . .
H2B H 0.009584 0.583376 0.584869 0.044 Uiso 1 1 calc R U . . .
C10 C -0.6785(3) 0.53537(14) 0.18875(12) 0.0325(4) Uani 1 1 d . . . . .
C1 C 0.0506(2) 0.71402(14) 0.49339(12) 0.0316(4) Uani 1 1 d . . . . .
C6 C -0.1182(3) 0.68586(15) 0.42759(13) 0.0368(4) Uani 1 1 d . . . . .
C5 C 0.2334(3) 0.66761(16) 0.46162(13) 0.0389(4) Uani 1 1 d . . . . .
H5A H 0.207284 0.596621 0.427644 0.047 Uiso 1 1 calc R U . . .
H5B H 0.286501 0.721299 0.420151 0.047 Uiso 1 1 calc R U . . .
O2 O -0.6057(3) 0.50746(14) 0.10485(11) 0.0683(6) Uani 1 1 d . . . . .
H2 H -0.562288 0.564926 0.082260 0.082 Uiso 1 1 calc R U . . .
C11 C -0.7607(3) 0.42816(16) 0.22353(14) 0.0409(5) Uani 1 1 d . . . . .
H11A H -0.771762 0.433170 0.290752 0.049 Uiso 1 1 calc R U . . .
H11B H -0.680391 0.363356 0.212791 0.049 Uiso 1 1 calc R U . . .
C3 C 0.2607(3) 0.66898(17) 0.63185(13) 0.0417(5) Uani 1 1 d . . . . .
H3A H 0.291429 0.611443 0.680377 0.050 Uiso 1 1 calc R U . . .
H3B H 0.290090 0.743224 0.659718 0.050 Uiso 1 1 calc R U . . .
C4 C 0.3713(3) 0.6491(2) 0.54998(15) 0.0515(6) Uani 1 1 d . . . . .
H4A H 0.479092 0.701657 0.552475 0.062 Uiso 1 1 calc R U . . .
H4B H 0.421576 0.572196 0.551699 0.062 Uiso 1 1 calc R U . . .
C12 C -0.9562(3) 0.41852(19) 0.16608(16) 0.0529(6) Uani 1 1 d . . . . .
H12A H -0.947834 0.376358 0.108091 0.064 Uiso 1 1 calc R U . . .
H12B H -1.045551 0.379668 0.201996 0.064 Uiso 1 1 calc R U . . .
C14 C -0.8509(3) 0.61156(17) 0.16922(18) 0.0542(6) Uani 1 1 d . . . . .
H14A H -0.836428 0.662540 0.116973 0.065 Uiso 1 1 calc R U . . .
H14B H -0.866790 0.656544 0.224878 0.065 Uiso 1 1 calc R U . . .
C13 C -1.0214(4) 0.5348(2) 0.1442(3) 0.0761(9) Uani 1 1 d . . . . .
H13A H -1.124459 0.554888 0.180822 0.091 Uiso 1 1 calc R U . . .
H13B H -1.069994 0.541707 0.077276 0.091 Uiso 1 1 calc R U . . .


_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 1.434(2) . ?
O1 H1 0.8400 . ?
C7 C6 1.198(3) . ?
C7 C8 1.381(3) . ?
C9 C8 1.198(3) . ?
C9 C10 1.472(3) . ?
C2 C3 1.526(3) . ?
C2 C1 1.530(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C10 O2 1.424(2) . ?
C10 C14 1.526(3) . ?
C10 C11 1.527(2) . ?
C1 C6 1.471(3) . ?
C1 C5 1.539(2) . ?
C5 C4 1.524(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
O2 H2 0.8400 . ?
C11 C12 1.528(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C3 C4 1.526(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C12 C13 1.492(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 C13 1.528(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

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 H1 109.5 . . ?
C6 C7 C8 178.1(2) . . ?
C8 C9 C10 178.32(19) . . ?
C9 C8 C7 177.0(2) . . ?
C3 C2 C1 103.60(15) . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
O2 C10 C9 109.19(15) . . ?
O2 C10 C14 110.88(17) . . ?
C9 C10 C14 113.06(15) . . ?
O2 C10 C11 106.36(14) . . ?
C9 C10 C11 113.55(15) . . ?
C14 C10 C11 103.52(16) . . ?
O1 C1 C6 111.20(14) . . ?
O1 C1 C2 106.24(14) . . ?
C6 C1 C2 114.05(15) . . ?
O1 C1 C5 110.58(14) . . ?
C6 C1 C5 111.82(15) . . ?
C2 C1 C5 102.51(14) . . ?
C7 C6 C1 176.00(19) . . ?
C4 C5 C1 106.05(15) . . ?
C4 C5 H5A 110.5 . . ?
C1 C5 H5A 110.5 . . ?
C4 C5 H5B 110.5 . . ?
C1 C5 H5B 110.5 . . ?
H5A C5 H5B 108.7 . . ?
C10 O2 H2 109.5 . . ?
C10 C11 C12 104.14(15) . . ?
C10 C11 H11A 110.9 . . ?
C12 C11 H11A 110.9 . . ?
C10 C11 H11B 110.9 . . ?
C12 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
C2 C3 C4 104.54(15) . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
C4 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C5 C4 C3 106.90(16) . . ?
C5 C4 H4A 110.3 . . ?
C3 C4 H4A 110.3 . . ?
C5 C4 H4B 110.3 . . ?
C3 C4 H4B 110.3 . . ?
H4A C4 H4B 108.6 . . ?
C13 C12 C11 106.25(18) . . ?
C13 C12 H12A 110.5 . . ?
C11 C12 H12A 110.5 . . ?
C13 C12 H12B 110.5 . . ?
C11 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C10 C14 C13 105.96(17) . . ?
C10 C14 H14A 110.5 . . ?
C13 C14 H14A 110.5 . . ?
C10 C14 H14B 110.5 . . ?
C13 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
C12 C13 C14 107.4(2) . . ?
C12 C13 H13A 110.2 . . ?
C14 C13 H13A 110.2 . . ?
C12 C13 H13B 110.2 . . ?
C14 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?

_refine_diff_density_max         0.409
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_1_CHCl3
_database_code_depnum_ccdc_archive 'CCDC 1855337'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10.50 H13.50 N0 O1.50'
_chemical_formula_weight         163.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_H-M_alt        'P 32 2 1'
_space_group_name_Hall           'P 32 2"'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'
'y, x, -z'

_cell_length_a                   14.250(7)
_cell_length_b                   14.250(7)
_cell_length_c                   6.620(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1164.2(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    365
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      13.20

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.934
_exptl_crystal_F_000             354
_exptl_transmission_factor_min   0.999
_exptl_transmission_factor_max   0.999
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.061
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            7074
_diffrn_reflns_av_unetI/netI     0.1471
_diffrn_reflns_av_R_equivalents  0.1239
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.650
_diffrn_reflns_theta_max         28.493
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1868
_reflns_number_gt                650
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_max     0.918
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.034 300 103 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?
_computing_data_collection       'Bruker SMART APEX-II'
_computing_cell_refinement       'Bruker SMART APEX-II'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1211P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 185 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1868
_refine_ls_number_parameters     74
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2045
_refine_ls_R_factor_gt           0.0835
_refine_ls_wR_factor_ref         0.2461
_refine_ls_wR_factor_gt          0.2036
_refine_ls_goodness_of_fit_ref   0.838
_refine_ls_restrained_S_all      0.838
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.2742(3) 0.5954(3) 0.1559(5) 0.0721(13) Uani 1 1 d . . . . .
H1 H 0.305290 0.618256 0.044170 0.087 Uiso 1 1 calc R U . . .
C1 C 0.2113(5) 0.4805(5) 0.1510(7) 0.0691(16) Uani 1 1 d . . . . .
C2 C 0.2824(7) 0.4309(6) 0.1000(9) 0.092(2) Uani 1 1 d . . . . .
H2A H 0.237761 0.357526 0.041965 0.111 Uiso 1 1 calc R U . . .
H2B H 0.338727 0.476629 0.000458 0.111 Uiso 1 1 calc R U . . .
C3 C 0.3325(9) 0.4252(11) 0.2884(12) 0.156(5) Uani 1 1 d . . . . .
H3B H 0.407975 0.486075 0.298830 0.187 Uiso 1 1 calc R U . . .
H3A H 0.332759 0.356002 0.298493 0.187 Uiso 1 1 calc R U . . .
C4 C 0.2595(11) 0.4331(10) 0.4557(13) 0.147(4) Uani 1 1 d . . . . .
H4A H 0.228873 0.367575 0.541798 0.176 Uiso 1 1 calc R U . . .
H4B H 0.303770 0.496935 0.542330 0.176 Uiso 1 1 calc R U . . .
C5 C 0.1706(5) 0.4431(6) 0.3631(8) 0.089(2) Uani 1 1 d . . . . .
H5B H 0.158791 0.497078 0.435645 0.107 Uiso 1 1 calc R U . . .
H5A H 0.102246 0.372617 0.362227 0.107 Uiso 1 1 calc R U . . .
C6 C 0.1194(5) 0.4446(5) 0.0077(8) 0.0693(16) Uani 1 1 d . . . . .
C7 C 0.0417(5) 0.4065(6) -0.1041(9) 0.0802(19) Uani 1 1 d . . . . .


_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 1.421(7) . ?
C1 C6 1.486(8) . ?
C1 C5 1.511(8) . ?
C1 C2 1.535(10) . ?
C2 C3 1.459(10) . ?
C3 C4 1.562(14) . ?
C4 C5 1.476(12) . ?
C6 C7 1.211(7) . ?
C7 C7 1.322(13) 5_554 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C6 110.5(5) . . ?
O1 C1 C5 107.1(5) . . ?
C6 C1 C5 110.8(5) . . ?
O1 C1 C2 110.8(5) . . ?
C6 C1 C2 111.9(5) . . ?
C5 C1 C2 105.5(5) . . ?
C3 C2 C1 107.0(5) . . ?
C2 C3 C4 103.9(8) . . ?
C5 C4 C3 110.3(7) . . ?
C4 C5 C1 102.9(6) . . ?
C7 C6 C1 174.5(7) . . ?
C6 C7 C7 178.8(8) . 5_554 ?

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_1_280K
_database_code_depnum_ccdc_archive 'CCDC 1855348'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
1,4-Bis(1-hydroxycyclopentyl)buta-1,3-diyne 
;
_chemical_name_common            ?
_chemical_melting_point          406K
_chemical_formula_moiety         'C14 H18 O2'
_chemical_formula_sum            'C14 H18 O2'
_chemical_formula_weight         218.28


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   6.9930(8)
_cell_length_b                   12.1747(14)
_cell_length_c                   14.8694(18)
_cell_angle_alpha                90
_cell_angle_beta                 97.493(2)
_cell_angle_gamma                90
_cell_volume                     1255.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    280(2)
_cell_measurement_reflns_used    1639
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      22.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9718
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      280(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            7154
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.169
_diffrn_reflns_theta_max         27.439
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2719
_reflns_number_gt                1704
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART APEX-II'
_computing_cell_refinement       'Bruker SMART APEX-II'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0900P)²+0.2440P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2719
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1906
_refine_ls_wR_factor_gt          0.1624
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.0494(2) 0.83275(11) 0.50587(10) 0.0692(5) Uani 1 1 d . . . . .
H1 H 0.058352 0.865149 0.458254 0.083 Uiso 1 1 calc R U . . .
C7 C -0.2527(4) 0.65817(18) 0.36858(15) 0.0622(6) Uani 1 1 d . . . . .
C9 C -0.5264(3) 0.58350(17) 0.25244(14) 0.0575(5) Uani 1 1 d . . . . .
C8 C -0.4010(3) 0.62063(17) 0.30585(15) 0.0601(6) Uani 1 1 d . . . . .
C2 C 0.0425(3) 0.66279(18) 0.58204(14) 0.0615(6) Uani 1 1 d . . . . .
H2A H -0.038284 0.703429 0.618697 0.074 Uiso 1 1 calc R U . . .
H2B H -0.004323 0.587859 0.575253 0.074 Uiso 1 1 calc R U . . .
C10 C -0.6801(3) 0.53497(15) 0.18769(13) 0.0532(5) Uani 1 1 d . . . . .
C1 C 0.0444(3) 0.71721(16) 0.48986(13) 0.0536(5) Uani 1 1 d . . . . .
C6 C -0.1219(3) 0.68787(18) 0.42315(15) 0.0602(6) Uani 1 1 d . . . . .
C5 C 0.2337(3) 0.6760(2) 0.46071(16) 0.0705(7) Uani 1 1 d . . . . .
H5A H 0.210908 0.611435 0.422560 0.085 Uiso 1 1 calc R U . . .
H5B H 0.291626 0.732419 0.426973 0.085 Uiso 1 1 calc R U . . .
O2 O -0.6035(3) 0.50397(13) 0.10749(11) 0.0791(6) Uani 1 1 d . . . . .
H2 H -0.559741 0.558312 0.084759 0.095 Uiso 1 1 calc R U . . .
C11 C -0.7656(4) 0.43112(19) 0.22346(16) 0.0702(6) Uani 1 1 d . . . . .
H11A H -0.688123 0.367371 0.213209 0.084 Uiso 1 1 calc R U . . .
H11B H -0.773836 0.437359 0.287876 0.084 Uiso 1 1 calc R U . . .
C3 C 0.2522(4) 0.6655(2) 0.62434(17) 0.0765(7) Uani 1 1 d . . . . .
H3A H 0.283990 0.735646 0.653407 0.092 Uiso 1 1 calc R U . . .
H3B H 0.278845 0.607466 0.668917 0.092 Uiso 1 1 calc R U . . .
C4 C 0.3636(4) 0.6484(3) 0.5461(2) 0.0977(9) Uani 1 1 d . . . . .
H4A H 0.405934 0.572609 0.544438 0.117 Uiso 1 1 calc R U . . .
H4B H 0.476574 0.695388 0.552336 0.117 Uiso 1 1 calc R U . . .
C12 C -0.9647(4) 0.4225(2) 0.1699(2) 0.0947(9) Uani 1 1 d . . . . .
H12A H -0.961232 0.375647 0.117378 0.114 Uiso 1 1 calc R U . . .
H12B H -1.054765 0.391455 0.207284 0.114 Uiso 1 1 calc R U . . .
C14 C -0.8543(4) 0.61021(19) 0.16590(19) 0.0754(7) Uani 1 1 d . . . . .
H14A H -0.872884 0.654747 0.218145 0.090 Uiso 1 1 calc R U . . .
H14B H -0.837265 0.658430 0.115622 0.090 Uiso 1 1 calc R U . . .
C13 C -1.0245(4) 0.5345(3) 0.1411(3) 0.1064(11) Uani 1 1 d . . . . .
H13A H -1.132375 0.557784 0.171375 0.128 Uiso 1 1 calc R U . . .
H13B H -1.064298 0.536298 0.076123 0.128 Uiso 1 1 calc R U . . .


_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 1.426(2) . ?
O1 H1 0.8200 . ?
C7 C6 1.197(3) . ?
C7 C8 1.379(3) . ?
C9 C8 1.193(3) . ?
C9 C10 1.470(3) . ?
C2 C3 1.519(3) . ?
C2 C1 1.524(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C10 O2 1.421(2) . ?
C10 C11 1.524(3) . ?
C10 C14 1.525(3) . ?
C1 C6 1.470(3) . ?
C1 C5 1.531(3) . ?
C5 C4 1.500(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
O2 H2 0.8200 . ?
C11 C12 1.514(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C3 C4 1.496(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C12 C13 1.473(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 C13 1.512(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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 H1 109.5 . . ?
C6 C7 C8 178.2(2) . . ?
C8 C9 C10 178.5(2) . . ?
C9 C8 C7 177.1(2) . . ?
C3 C2 C1 103.99(19) . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
O2 C10 C9 109.46(17) . . ?
O2 C10 C11 106.31(16) . . ?
C9 C10 C11 113.06(17) . . ?
O2 C10 C14 111.06(18) . . ?
C9 C10 C14 113.16(17) . . ?
C11 C10 C14 103.49(19) . . ?
O1 C1 C6 110.64(16) . . ?
O1 C1 C2 106.35(16) . . ?
C6 C1 C2 113.72(18) . . ?
O1 C1 C5 111.54(18) . . ?
C6 C1 C5 111.49(17) . . ?
C2 C1 C5 102.79(18) . . ?
C7 C6 C1 176.3(2) . . ?
C4 C5 C1 106.52(19) . . ?
C4 C5 H5A 110.4 . . ?
C1 C5 H5A 110.4 . . ?
C4 C5 H5B 110.4 . . ?
C1 C5 H5B 110.4 . . ?
H5A C5 H5B 108.6 . . ?
C10 O2 H2 109.5 . . ?
C12 C11 C10 104.45(19) . . ?
C12 C11 H11A 110.9 . . ?
C10 C11 H11A 110.9 . . ?
C12 C11 H11B 110.9 . . ?
C10 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
C4 C3 C2 104.4(2) . . ?
C4 C3 H3A 110.9 . . ?
C2 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
C2 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
C3 C4 C5 107.9(2) . . ?
C3 C4 H4A 110.1 . . ?
C5 C4 H4A 110.1 . . ?
C3 C4 H4B 110.1 . . ?
C5 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
C13 C12 C11 107.2(2) . . ?
C13 C12 H12A 110.3 . . ?
C11 C12 H12A 110.3 . . ?
C13 C12 H12B 110.3 . . ?
C11 C12 H12B 110.3 . . ?
H12A C12 H12B 108.5 . . ?
C13 C14 C10 105.5(2) . . ?
C13 C14 H14A 110.6 . . ?
C10 C14 H14A 110.6 . . ?
C13 C14 H14B 110.6 . . ?
C10 C14 H14B 110.6 . . ?
H14A C14 H14B 108.8 . . ?
C12 C13 C14 108.0(2) . . ?
C12 C13 H13A 110.1 . . ?
C14 C13 H13A 110.1 . . ?
C12 C13 H13B 110.1 . . ?
C14 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_1_220K
_database_code_depnum_ccdc_archive 'CCDC 1855345'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
1,4-Bis(1-hydroxycyclopentyl)buta-1,3-diyne 
;
_chemical_name_common            ?
_chemical_melting_point          406K
_chemical_formula_moiety         'C14 H18 O2'
_chemical_formula_sum            'C14 H18 O2'
_chemical_formula_weight         218.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   7.0442(7)
_cell_length_b                   12.0864(11)
_cell_length_c                   14.7091(14)
_cell_angle_alpha                90
_cell_angle_beta                 97.5090(10)
_cell_angle_gamma                90
_cell_volume                     1241.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    1924
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      23.77

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9715
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            7063
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.189
_diffrn_reflns_theta_max         27.464
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2695
_reflns_number_gt                1929
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART APEX-II'
_computing_cell_refinement       'Bruker SMART APEX-II'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0719P)²+0.4093P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2695
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1647
_refine_ls_wR_factor_gt          0.1472
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.0568(2) 0.83217(10) 0.50742(9) 0.0534(4) Uani 1 1 d . . . . .
H1 H 0.065800 0.864842 0.458538 0.064 Uiso 1 1 calc R U . . .
C7 C -0.2513(3) 0.65764(16) 0.37037(13) 0.0487(5) Uani 1 1 d . . . . .
C9 C -0.5259(3) 0.58382(15) 0.25325(13) 0.0451(5) Uani 1 1 d . . . . .
C8 C -0.4002(3) 0.62091(15) 0.30732(13) 0.0471(5) Uani 1 1 d . . . . .
C2 C 0.0467(3) 0.66145(15) 0.58502(13) 0.0481(5) Uani 1 1 d . . . . .
H2A H -0.034982 0.702547 0.622280 0.058 Uiso 1 1 calc R U . . .
H2B H 0.001723 0.584757 0.578811 0.058 Uiso 1 1 calc R U . . .
C10 C -0.6799(3) 0.53554(14) 0.18779(12) 0.0422(4) Uani 1 1 d . . . . .
C1 C 0.0467(3) 0.71539(14) 0.49129(12) 0.0415(4) Uani 1 1 d . . . . .
C6 C -0.1200(3) 0.68710(16) 0.42496(13) 0.0472(5) Uani 1 1 d . . . . .
C5 C 0.2339(3) 0.67188(18) 0.46092(14) 0.0537(5) Uani 1 1 d . . . . .
H5A H 0.209581 0.604500 0.424184 0.064 Uiso 1 1 calc R U . . .
H5B H 0.290054 0.727583 0.424023 0.064 Uiso 1 1 calc R U . . .
O2 O -0.6042(3) 0.50482(12) 0.10631(10) 0.0690(5) Uani 1 1 d . . . . .
H2 H -0.560077 0.560371 0.083328 0.083 Uiso 1 1 calc R U . . .
C11 C -0.7645(3) 0.43017(17) 0.22350(14) 0.0548(5) Uani 1 1 d . . . . .
H11A H -0.685798 0.365624 0.213305 0.066 Uiso 1 1 calc R U . . .
H11B H -0.774261 0.436257 0.289169 0.066 Uiso 1 1 calc R U . . .
C3 C 0.2555(3) 0.66632(18) 0.62738(14) 0.0572(6) Uani 1 1 d . . . . .
H3A H 0.286011 0.738596 0.655785 0.069 Uiso 1 1 calc R U . . .
H3B H 0.283698 0.608575 0.673955 0.069 Uiso 1 1 calc R U . . .
C4 C 0.3676(4) 0.6476(2) 0.54791(17) 0.0730(7) Uani 1 1 d . . . . .
H4A H 0.412806 0.570940 0.547699 0.088 Uiso 1 1 calc R U . . .
H4B H 0.478908 0.696922 0.552752 0.088 Uiso 1 1 calc R U . . .
C12 C -0.9615(4) 0.4211(2) 0.16820(19) 0.0717(7) Uani 1 1 d . . . . .
H12A H -0.955672 0.375984 0.113300 0.086 Uiso 1 1 calc R U . . .
H12B H -1.051705 0.386658 0.205017 0.086 Uiso 1 1 calc R U . . .
C14 C -0.8528(3) 0.61150(18) 0.16677(17) 0.0621(6) Uani 1 1 d . . . . .
H14A H -0.869992 0.656651 0.220435 0.075 Uiso 1 1 calc R U . . .
H14B H -0.836516 0.660803 0.115468 0.075 Uiso 1 1 calc R U . . .
C13 C -1.0240(4) 0.5357(2) 0.1420(3) 0.0901(9) Uani 1 1 d . . . . .
H13A H -1.129734 0.558008 0.175155 0.108 Uiso 1 1 calc R U . . .
H13B H -1.067829 0.539612 0.076062 0.108 Uiso 1 1 calc R U . . .


_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 1.432(2) . ?
O1 H1 0.8300 . ?
C7 C6 1.197(3) . ?
C7 C8 1.380(3) . ?
C9 C8 1.197(3) . ?
C9 C10 1.474(3) . ?
C2 C3 1.522(3) . ?
C2 C1 1.525(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C10 O2 1.423(2) . ?
C10 C14 1.524(3) . ?
C10 C11 1.528(3) . ?
C1 C6 1.466(3) . ?
C1 C5 1.539(3) . ?
C5 C4 1.515(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
O2 H2 0.8300 . ?
C11 C12 1.518(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C3 C4 1.511(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C12 C13 1.488(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C14 C13 1.520(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?

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 H1 109.5 . . ?
C6 C7 C8 178.4(2) . . ?
C8 C9 C10 178.6(2) . . ?
C9 C8 C7 176.7(2) . . ?
C3 C2 C1 103.86(16) . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
O2 C10 C9 109.17(16) . . ?
O2 C10 C14 111.33(17) . . ?
C9 C10 C14 113.25(16) . . ?
O2 C10 C11 106.14(15) . . ?
C9 C10 C11 113.10(15) . . ?
C14 C10 C11 103.56(17) . . ?
O1 C1 C6 111.01(15) . . ?
O1 C1 C2 106.11(14) . . ?
C6 C1 C2 114.05(16) . . ?
O1 C1 C5 111.03(15) . . ?
C6 C1 C5 111.68(15) . . ?
C2 C1 C5 102.56(15) . . ?
C7 C6 C1 175.9(2) . . ?
C4 C5 C1 106.42(17) . . ?
C4 C5 H5A 110.4 . . ?
C1 C5 H5A 110.4 . . ?
C4 C5 H5B 110.4 . . ?
C1 C5 H5B 110.4 . . ?
H5A C5 H5B 108.6 . . ?
C10 O2 H2 109.5 . . ?
C12 C11 C10 104.24(17) . . ?
C12 C11 H11A 110.9 . . ?
C10 C11 H11A 110.9 . . ?
C12 C11 H11B 110.9 . . ?
C10 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
C4 C3 C2 104.62(17) . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C3 C4 C5 107.11(18) . . ?
C3 C4 H4A 110.3 . . ?
C5 C4 H4A 110.3 . . ?
C3 C4 H4B 110.3 . . ?
C5 C4 H4B 110.3 . . ?
H4A C4 H4B 108.5 . . ?
C13 C12 C11 106.9(2) . . ?
C13 C12 H12A 110.3 . . ?
C11 C12 H12A 110.3 . . ?
C13 C12 H12B 110.3 . . ?
C11 C12 H12B 110.3 . . ?
H12A C12 H12B 108.6 . . ?
C13 C14 C10 105.85(18) . . ?
C13 C14 H14A 110.6 . . ?
C10 C14 H14A 110.6 . . ?
C13 C14 H14B 110.6 . . ?
C10 C14 H14B 110.6 . . ?
H14A C14 H14B 108.7 . . ?
C12 C13 C14 107.5(2) . . ?
C12 C13 H13A 110.2 . . ?
C14 C13 H13A 110.2 . . ?
C12 C13 H13B 110.2 . . ?
C14 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?

_refine_diff_density_max         0.289
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_1_200K
_database_code_depnum_ccdc_archive 'CCDC 1855344'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
1,4-Bis(1-hydroxycyclopentyl)buta-1,3-diyne 
;
_chemical_name_common            ?
_chemical_melting_point          406K
_chemical_formula_moiety         'C14 H18 O2'
_chemical_formula_sum            'C14 H18 O2'
_chemical_formula_weight         218.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   7.0671(7)
_cell_length_b                   12.0636(11)
_cell_length_c                   14.6451(13)
_cell_angle_alpha                90
_cell_angle_beta                 97.5340(10)
_cell_angle_gamma                90
_cell_volume                     1237.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2031
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      25.04

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9715
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            7058
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.195
_diffrn_reflns_theta_max         27.550
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2692
_reflns_number_gt                1989
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART APEX-II'
_computing_cell_refinement       'Bruker SMART APEX-II'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0730P)²+0.4356P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2692
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1622
_refine_ls_wR_factor_gt          0.1465
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.0600(2) 0.83214(10) 0.50789(9) 0.0493(4) Uani 1 1 d . . . . .
H1 H 0.068668 0.865036 0.458054 0.059 Uiso 1 1 calc R U . . .
C7 C -0.2510(3) 0.65760(15) 0.37104(13) 0.0450(5) Uani 1 1 d . . . . .
C9 C -0.5258(3) 0.58384(15) 0.25374(13) 0.0417(4) Uani 1 1 d . . . . .
C8 C -0.4001(3) 0.62084(15) 0.30798(13) 0.0431(4) Uani 1 1 d . . . . .
C2 C 0.0487(3) 0.66122(15) 0.58642(12) 0.0437(5) Uani 1 1 d . . . . .
H2A H -0.033923 0.702711 0.624101 0.052 Uiso 1 1 calc R U . . .
H2B H 0.004175 0.583428 0.580390 0.052 Uiso 1 1 calc R U . . .
C10 C -0.6793(3) 0.53537(14) 0.18816(11) 0.0392(4) Uani 1 1 d . . . . .
C1 C 0.0480(3) 0.71499(14) 0.49189(12) 0.0385(4) Uani 1 1 d . . . . .
C6 C -0.1195(3) 0.68677(15) 0.42585(13) 0.0433(4) Uani 1 1 d . . . . .
C5 C 0.2340(3) 0.67059(17) 0.46118(14) 0.0486(5) Uani 1 1 d . . . . .
H5A H 0.208793 0.601749 0.424808 0.058 Uiso 1 1 calc R U . . .
H5B H 0.289736 0.726193 0.422757 0.058 Uiso 1 1 calc R U . . .
O2 O -0.6044(2) 0.50530(12) 0.10602(10) 0.0672(5) Uani 1 1 d . . . . .
H2 H -0.560617 0.561904 0.082741 0.081 Uiso 1 1 calc R U . . .
C11 C -0.7632(3) 0.42962(16) 0.22354(14) 0.0491(5) Uani 1 1 d . . . . .
H11A H -0.683426 0.364505 0.213151 0.059 Uiso 1 1 calc R U . . .
H11B H -0.773431 0.435459 0.290134 0.059 Uiso 1 1 calc R U . . .
C3 C 0.2570(3) 0.66697(17) 0.62890(13) 0.0516(5) Uani 1 1 d . . . . .
H3A H 0.287268 0.740447 0.657218 0.062 Uiso 1 1 calc R U . . .
H3B H 0.286136 0.608992 0.676502 0.062 Uiso 1 1 calc R U . . .
C4 C 0.3690(3) 0.6476(2) 0.54842(16) 0.0655(6) Uani 1 1 d . . . . .
H4A H 0.480337 0.698060 0.552624 0.079 Uiso 1 1 calc R U . . .
H4B H 0.415509 0.570223 0.548695 0.079 Uiso 1 1 calc R U . . .
C12 C -0.9599(3) 0.4204(2) 0.16741(17) 0.0653(6) Uani 1 1 d . . . . .
H12A H -0.953173 0.375791 0.111212 0.078 Uiso 1 1 calc R U . . .
H12B H -1.050546 0.384426 0.204214 0.078 Uiso 1 1 calc R U . . .
C14 C -0.8519(3) 0.61151(17) 0.16704(17) 0.0588(6) Uani 1 1 d . . . . .
H14A H -0.868827 0.657368 0.221441 0.071 Uiso 1 1 calc R U . . .
H14B H -0.835677 0.661261 0.114871 0.071 Uiso 1 1 calc R U . . .
C13 C -1.0232(4) 0.5355(2) 0.1424(2) 0.0862(9) Uani 1 1 d . . . . .
H13A H -1.128642 0.557431 0.176906 0.103 Uiso 1 1 calc R U . . .
H13B H -1.069004 0.540223 0.075676 0.103 Uiso 1 1 calc R U . . .


_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 1.433(2) . ?
O1 H1 0.8400 . ?
C7 C6 1.198(3) . ?
C7 C8 1.380(3) . ?
C9 C8 1.197(3) . ?
C9 C10 1.472(3) . ?
C2 C3 1.523(3) . ?
C2 C1 1.528(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C10 O2 1.423(2) . ?
C10 C11 1.526(2) . ?
C10 C14 1.526(3) . ?
C1 C6 1.467(3) . ?
C1 C5 1.540(3) . ?
C5 C4 1.517(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
O2 H2 0.8400 . ?
C11 C12 1.524(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C3 C4 1.521(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C12 C13 1.489(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 C13 1.524(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

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 H1 109.5 . . ?
C6 C7 C8 178.3(2) . . ?
C8 C9 C10 178.45(19) . . ?
C9 C8 C7 176.8(2) . . ?
C3 C2 C1 103.81(15) . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
O2 C10 C9 109.18(15) . . ?
O2 C10 C11 106.14(14) . . ?
C9 C10 C11 113.36(15) . . ?
O2 C10 C14 110.98(16) . . ?
C9 C10 C14 113.22(15) . . ?
C11 C10 C14 103.66(16) . . ?
O1 C1 C6 111.22(14) . . ?
O1 C1 C2 106.10(14) . . ?
C6 C1 C2 113.89(15) . . ?
O1 C1 C5 110.88(15) . . ?
C6 C1 C5 111.87(15) . . ?
C2 C1 C5 102.45(15) . . ?
C7 C6 C1 175.95(19) . . ?
C4 C5 C1 106.51(16) . . ?
C4 C5 H5A 110.4 . . ?
C1 C5 H5A 110.4 . . ?
C4 C5 H5B 110.4 . . ?
C1 C5 H5B 110.4 . . ?
H5A C5 H5B 108.6 . . ?
C10 O2 H2 109.5 . . ?
C12 C11 C10 104.20(16) . . ?
C12 C11 H11A 110.9 . . ?
C10 C11 H11A 110.9 . . ?
C12 C11 H11B 110.9 . . ?
C10 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
C4 C3 C2 104.47(16) . . ?
C4 C3 H3A 110.9 . . ?
C2 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
C2 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
C5 C4 C3 106.91(17) . . ?
C5 C4 H4A 110.3 . . ?
C3 C4 H4A 110.3 . . ?
C5 C4 H4B 110.3 . . ?
C3 C4 H4B 110.3 . . ?
H4A C4 H4B 108.6 . . ?
C13 C12 C11 106.76(19) . . ?
C13 C12 H12A 110.4 . . ?
C11 C12 H12A 110.4 . . ?
C13 C12 H12B 110.4 . . ?
C11 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
C13 C14 C10 105.94(18) . . ?
C13 C14 H14A 110.5 . . ?
C10 C14 H14A 110.5 . . ?
C13 C14 H14B 110.5 . . ?
C10 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
C12 C13 C14 107.4(2) . . ?
C12 C13 H13A 110.2 . . ?
C14 C13 H13A 110.2 . . ?
C12 C13 H13B 110.2 . . ?
C14 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_1_240K
_database_code_depnum_ccdc_archive 'CCDC 1855346'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
1,4-Bis(1-hydroxycyclopentyl)buta-1,3-diyne 
;
_chemical_name_common            ?
_chemical_melting_point          406K
_chemical_formula_moiety         'C14 H18 O2'
_chemical_formula_sum            'C14 H18 O2'
_chemical_formula_weight         218.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   7.0251(8)
_cell_length_b                   12.1145(13)
_cell_length_c                   14.7700(16)
_cell_angle_alpha                90
_cell_angle_beta                 97.488(2)
_cell_angle_gamma                90
_cell_volume                     1246.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    1821
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      23.70

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9716
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_process_details   SADABAS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      240(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            7102
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.182
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2707
_reflns_number_gt                1850
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART APEX-II'
_computing_cell_refinement       'Bruker SMART APEX-II'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0755P)²+0.3185P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2707
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1680
_refine_ls_wR_factor_gt          0.1498
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.0541(2) 0.83240(10) 0.50688(9) 0.0578(4) Uani 1 1 d . . . . .
H1 H 0.063219 0.865206 0.458300 0.069 Uiso 1 1 calc R U . . .
C7 C -0.2516(3) 0.65790(16) 0.36958(13) 0.0523(5) Uani 1 1 d . . . . .
C9 C -0.5258(3) 0.58386(15) 0.25283(13) 0.0487(5) Uani 1 1 d . . . . .
C8 C -0.4005(3) 0.62078(16) 0.30693(14) 0.0512(5) Uani 1 1 d . . . . .
C2 C 0.0449(3) 0.66167(16) 0.58386(13) 0.0521(5) Uani 1 1 d . . . . .
H2A H -0.036980 0.702666 0.621006 0.063 Uiso 1 1 calc R U . . .
H2B H -0.000753 0.585273 0.577358 0.063 Uiso 1 1 calc R U . . .
C10 C -0.6800(3) 0.53524(14) 0.18776(12) 0.0458(5) Uani 1 1 d . . . . .
C1 C 0.0457(3) 0.71596(14) 0.49064(12) 0.0450(5) Uani 1 1 d . . . . .
C6 C -0.1211(3) 0.68727(16) 0.42411(14) 0.0510(5) Uani 1 1 d . . . . .
C5 C 0.2341(3) 0.67321(18) 0.46078(14) 0.0588(6) Uani 1 1 d . . . . .
H5A H 0.210332 0.606641 0.423310 0.071 Uiso 1 1 calc R U . . .
H5B H 0.291343 0.729463 0.425016 0.071 Uiso 1 1 calc R U . . .
O2 O -0.6042(2) 0.50445(12) 0.10670(10) 0.0718(5) Uani 1 1 d . . . . .
H2 H -0.560282 0.559845 0.083640 0.086 Uiso 1 1 calc R U . . .
C11 C -0.7648(3) 0.43052(17) 0.22348(14) 0.0595(5) Uani 1 1 d . . . . .
H11A H -0.686240 0.365990 0.213272 0.071 Uiso 1 1 calc R U . . .
H11B H -0.774246 0.436723 0.288900 0.071 Uiso 1 1 calc R U . . .
C3 C 0.2541(3) 0.66591(18) 0.62626(14) 0.0627(6) Uani 1 1 d . . . . .
H3A H 0.285065 0.737800 0.654868 0.075 Uiso 1 1 calc R U . . .
H3B H 0.281809 0.607975 0.672401 0.075 Uiso 1 1 calc R U . . .
C4 C 0.3662(4) 0.6476(2) 0.54738(18) 0.0802(7) Uani 1 1 d . . . . .
H4A H 0.410215 0.570829 0.546678 0.096 Uiso 1 1 calc R U . . .
H4B H 0.478753 0.696068 0.552817 0.096 Uiso 1 1 calc R U . . .
C12 C -0.9626(4) 0.4218(2) 0.16861(19) 0.0787(7) Uani 1 1 d . . . . .
H12A H -0.957403 0.375864 0.114360 0.094 Uiso 1 1 calc R U . . .
H12B H -1.053278 0.388321 0.205665 0.094 Uiso 1 1 calc R U . . .
C14 C -0.8534(3) 0.61108(18) 0.16627(17) 0.0665(6) Uani 1 1 d . . . . .
H14A H -0.871240 0.656285 0.219543 0.080 Uiso 1 1 calc R U . . .
H14B H -0.836539 0.660088 0.115135 0.080 Uiso 1 1 calc R U . . .
C13 C -1.0242(4) 0.5354(2) 0.1415(3) 0.0947(9) Uani 1 1 d . . . . .
H13A H -1.131136 0.558120 0.173748 0.114 Uiso 1 1 calc R U . . .
H13B H -1.066771 0.538548 0.075673 0.114 Uiso 1 1 calc R U . . .


_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 1.431(2) . ?
O1 H1 0.8300 . ?
C7 C6 1.193(3) . ?
C7 C8 1.379(3) . ?
C9 C8 1.196(3) . ?
C9 C10 1.474(3) . ?
C2 C3 1.522(3) . ?
C2 C1 1.527(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C10 O2 1.422(2) . ?
C10 C11 1.525(3) . ?
C10 C14 1.526(3) . ?
C1 C6 1.469(3) . ?
C1 C5 1.538(3) . ?
C5 C4 1.512(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
O2 H2 0.8300 . ?
C11 C12 1.518(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C3 C4 1.505(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C12 C13 1.482(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C14 C13 1.517(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?

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 H1 109.5 . . ?
C6 C7 C8 178.3(2) . . ?
C8 C9 C10 178.3(2) . . ?
C9 C8 C7 177.0(2) . . ?
C3 C2 C1 103.86(16) . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
O2 C10 C9 109.25(16) . . ?
O2 C10 C11 106.21(15) . . ?
C9 C10 C11 113.21(16) . . ?
O2 C10 C14 111.05(17) . . ?
C9 C10 C14 113.21(16) . . ?
C11 C10 C14 103.61(17) . . ?
O1 C1 C6 110.94(15) . . ?
O1 C1 C2 106.17(14) . . ?
C6 C1 C2 113.88(16) . . ?
O1 C1 C5 111.19(16) . . ?
C6 C1 C5 111.68(16) . . ?
C2 C1 C5 102.60(16) . . ?
C7 C6 C1 176.1(2) . . ?
C4 C5 C1 106.43(17) . . ?
C4 C5 H5A 110.4 . . ?
C1 C5 H5A 110.4 . . ?
C4 C5 H5B 110.4 . . ?
C1 C5 H5B 110.4 . . ?
H5A C5 H5B 108.6 . . ?
C10 O2 H2 109.5 . . ?
C12 C11 C10 104.19(17) . . ?
C12 C11 H11A 110.9 . . ?
C10 C11 H11A 110.9 . . ?
C12 C11 H11B 110.9 . . ?
C10 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
C4 C3 C2 104.55(17) . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C3 C4 C5 107.40(19) . . ?
C3 C4 H4A 110.2 . . ?
C5 C4 H4A 110.2 . . ?
C3 C4 H4B 110.2 . . ?
C5 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
C13 C12 C11 107.1(2) . . ?
C13 C12 H12A 110.3 . . ?
C11 C12 H12A 110.3 . . ?
C13 C12 H12B 110.3 . . ?
C11 C12 H12B 110.3 . . ?
H12A C12 H12B 108.5 . . ?
C13 C14 C10 105.74(18) . . ?
C13 C14 H14A 110.6 . . ?
C10 C14 H14A 110.6 . . ?
C13 C14 H14B 110.6 . . ?
C10 C14 H14B 110.6 . . ?
H14A C14 H14B 108.7 . . ?
C12 C13 C14 107.6(2) . . ?
C12 C13 H13A 110.2 . . ?
C14 C13 H13A 110.2 . . ?
C12 C13 H13B 110.2 . . ?
C14 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?

_refine_diff_density_max         0.247
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_1_180K
_database_code_depnum_ccdc_archive 'CCDC 1855343'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
1,4-Bis(1-hydroxycyclopentyl)buta-1,3-diyne 
;
_chemical_name_common            ?
_chemical_melting_point          406K
_chemical_formula_moiety         'C14 H18 O2'
_chemical_formula_sum            'C14 H18 O2'
_chemical_formula_weight         218.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   7.0911(7)
_cell_length_b                   12.0408(11)
_cell_length_c                   14.5761(13)
_cell_angle_alpha                90
_cell_angle_beta                 97.5520(10)
_cell_angle_gamma                90
_cell_volume                     1233.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    2151
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      27.05

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9714
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            7017
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.202
_diffrn_reflns_theta_max         27.537
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2670
_reflns_number_gt                2022
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART APEX-II'
_computing_cell_refinement       'Bruker SMART APEX-II'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0712P)²+0.4979P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2670
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1605
_refine_ls_wR_factor_gt          0.1467
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.0630(2) 0.83203(10) 0.50815(9) 0.0449(4) Uani 1 1 d . . . . .
H1 H 0.071871 0.864469 0.457877 0.054 Uiso 1 1 calc R U . . .
C7 C -0.2506(3) 0.65743(15) 0.37204(13) 0.0407(4) Uani 1 1 d . . . . .
C9 C -0.5257(3) 0.58387(15) 0.25437(13) 0.0379(4) Uani 1 1 d . . . . .
C8 C -0.3998(3) 0.62077(15) 0.30885(13) 0.0392(4) Uani 1 1 d . . . . .
C2 C 0.0510(3) 0.66135(15) 0.58815(12) 0.0393(4) Uani 1 1 d . . . . .
H2A H -0.031162 0.703083 0.625971 0.047 Uiso 1 1 calc R U . . .
H2B H 0.007042 0.583306 0.582556 0.047 Uiso 1 1 calc R U . . .
C10 C -0.6787(3) 0.53540(14) 0.18854(11) 0.0350(4) Uani 1 1 d . . . . .
C1 C 0.0495(2) 0.71465(14) 0.49277(12) 0.0341(4) Uani 1 1 d . . . . .
C6 C -0.1186(3) 0.68650(15) 0.42656(13) 0.0395(4) Uani 1 1 d . . . . .
C5 C 0.2338(3) 0.66894(16) 0.46139(13) 0.0433(5) Uani 1 1 d . . . . .
H5A H 0.207813 0.599009 0.426270 0.052 Uiso 1 1 calc R U . . .
H5B H 0.288339 0.723470 0.421399 0.052 Uiso 1 1 calc R U . . .
O2 O -0.6040(3) 0.50588(13) 0.10561(10) 0.0664(5) Uani 1 1 d . . . . .
H2 H -0.560849 0.562827 0.082410 0.080 Uiso 1 1 calc R U . . .
C11 C -0.7622(3) 0.42910(16) 0.22374(14) 0.0447(5) Uani 1 1 d . . . . .
H11A H -0.773014 0.434716 0.290608 0.054 Uiso 1 1 calc R U . . .
H11B H -0.682287 0.364035 0.213351 0.054 Uiso 1 1 calc R U . . .
C3 C 0.2592(3) 0.66778(17) 0.63035(13) 0.0460(5) Uani 1 1 d . . . . .
H3A H 0.289143 0.741607 0.658443 0.055 Uiso 1 1 calc R U . . .
H3B H 0.289179 0.610010 0.678378 0.055 Uiso 1 1 calc R U . . .
C4 C 0.3701(3) 0.6482(2) 0.54915(16) 0.0588(6) Uani 1 1 d . . . . .
H4A H 0.479727 0.699616 0.552482 0.071 Uiso 1 1 calc R U . . .
H4B H 0.418426 0.571008 0.550126 0.071 Uiso 1 1 calc R U . . .
C12 C -0.9583(3) 0.41980(19) 0.16676(17) 0.0588(6) Uani 1 1 d . . . . .
H12A H -0.950731 0.376323 0.109715 0.071 Uiso 1 1 calc R U . . .
H12B H -1.048597 0.382507 0.203057 0.071 Uiso 1 1 calc R U . . .
C14 C -0.8513(3) 0.61172(17) 0.16795(17) 0.0559(6) Uani 1 1 d . . . . .
H14A H -0.867738 0.657316 0.222861 0.067 Uiso 1 1 calc R U . . .
H14B H -0.835784 0.661895 0.115662 0.067 Uiso 1 1 calc R U . . .
C13 C -1.0220(4) 0.5353(2) 0.1432(3) 0.0807(9) Uani 1 1 d . . . . .
H13A H -1.126300 0.556536 0.178737 0.097 Uiso 1 1 calc R U . . .
H13B H -1.069231 0.541113 0.076405 0.097 Uiso 1 1 calc R U . . .


_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 1.432(2) . ?
O1 H1 0.8400 . ?
C7 C6 1.198(3) . ?
C7 C8 1.381(3) . ?
C9 C8 1.199(3) . ?
C9 C10 1.472(3) . ?
C2 C3 1.525(3) . ?
C2 C1 1.530(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C10 O2 1.427(2) . ?
C10 C11 1.527(2) . ?
C10 C14 1.528(3) . ?
C1 C6 1.471(3) . ?
C1 C5 1.541(2) . ?
C5 C4 1.519(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
O2 H2 0.8400 . ?
C11 C12 1.528(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C3 C4 1.523(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C12 C13 1.489(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 C13 1.525(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

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 H1 109.5 . . ?
C6 C7 C8 178.2(2) . . ?
C8 C9 C10 178.37(19) . . ?
C9 C8 C7 176.8(2) . . ?
C3 C2 C1 103.63(15) . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
O2 C10 C9 109.09(15) . . ?
O2 C10 C11 106.21(14) . . ?
C9 C10 C11 113.48(15) . . ?
O2 C10 C14 111.11(17) . . ?
C9 C10 C14 113.11(15) . . ?
C11 C10 C14 103.56(16) . . ?
O1 C1 C6 111.22(14) . . ?
O1 C1 C2 106.22(14) . . ?
C6 C1 C2 114.05(15) . . ?
O1 C1 C5 110.92(15) . . ?
C6 C1 C5 111.60(15) . . ?
C2 C1 C5 102.42(15) . . ?
C7 C6 C1 176.06(19) . . ?
C4 C5 C1 106.22(15) . . ?
C4 C5 H5A 110.5 . . ?
C1 C5 H5A 110.5 . . ?
C4 C5 H5B 110.5 . . ?
C1 C5 H5B 110.5 . . ?
H5A C5 H5B 108.7 . . ?
C10 O2 H2 109.5 . . ?
C10 C11 C12 104.13(16) . . ?
C10 C11 H11A 110.9 . . ?
C12 C11 H11A 110.9 . . ?
C10 C11 H11B 110.9 . . ?
C12 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
C4 C3 C2 104.48(16) . . ?
C4 C3 H3A 110.9 . . ?
C2 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
C2 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
C5 C4 C3 107.00(17) . . ?
C5 C4 H4A 110.3 . . ?
C3 C4 H4A 110.3 . . ?
C5 C4 H4B 110.3 . . ?
C3 C4 H4B 110.3 . . ?
H4A C4 H4B 108.6 . . ?
C13 C12 C11 106.48(19) . . ?
C13 C12 H12A 110.4 . . ?
C11 C12 H12A 110.4 . . ?
C13 C12 H12B 110.4 . . ?
C11 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
C13 C14 C10 105.90(17) . . ?
C13 C14 H14A 110.6 . . ?
C10 C14 H14A 110.6 . . ?
C13 C14 H14B 110.6 . . ?
C10 C14 H14B 110.6 . . ?
H14A C14 H14B 108.7 . . ?
C12 C13 C14 107.6(2) . . ?
C12 C13 H13A 110.2 . . ?
C14 C13 H13A 110.2 . . ?
C12 C13 H13B 110.2 . . ?
C14 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?

_refine_diff_density_max         0.401
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_1_260K
_database_code_depnum_ccdc_archive 'CCDC 1855347'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
1,4-Bis(1-hydroxycyclopentyl)buta-1,3-diyne 
;
_chemical_name_common            ?
_chemical_melting_point          406K
_chemical_formula_moiety         'C14 H18 O2'
_chemical_formula_sum            'C14 H18 O2'
_chemical_formula_weight         218.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   7.0076(8)
_cell_length_b                   12.1420(15)
_cell_length_c                   14.8216(18)
_cell_angle_alpha                90
_cell_angle_beta                 97.481(2)
_cell_angle_gamma                90
_cell_volume                     1250.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    260(2)
_cell_measurement_reflns_used    1723
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      22.06

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9717
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      260(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            7111
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.176
_diffrn_reflns_theta_max         27.446
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2709
_reflns_number_gt                1778
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART APEX-II'
_computing_cell_refinement       'Bruker SMART APEX-II'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0790P)²+0.3127P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2709
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1754
_refine_ls_wR_factor_gt          0.1527
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.0517(2) 0.83253(11) 0.50643(9) 0.0630(5) Uani 1 1 d . . . . .
H1 H 0.061128 0.864981 0.458686 0.076 Uiso 1 1 calc R U . . .
C7 C -0.2519(3) 0.65806(17) 0.36912(14) 0.0570(5) Uani 1 1 d . . . . .
C9 C -0.5261(3) 0.58352(16) 0.25260(14) 0.0533(5) Uani 1 1 d . . . . .
C8 C -0.4006(3) 0.62064(16) 0.30626(14) 0.0556(5) Uani 1 1 d . . . . .
C2 C 0.0436(3) 0.66220(17) 0.58282(14) 0.0570(5) Uani 1 1 d . . . . .
H2A H -0.037160 0.702916 0.619525 0.068 Uiso 1 1 calc R U . . .
H2B H -0.002633 0.586951 0.576257 0.068 Uiso 1 1 calc R U . . .
C10 C -0.6802(3) 0.53515(15) 0.18769(12) 0.0490(5) Uani 1 1 d . . . . .
C1 C 0.0447(3) 0.71638(15) 0.49017(12) 0.0487(5) Uani 1 1 d . . . . .
C6 C -0.1212(3) 0.68749(16) 0.42374(14) 0.0551(5) Uani 1 1 d . . . . .
C5 C 0.2341(3) 0.6747(2) 0.46074(15) 0.0646(6) Uani 1 1 d . . . . .
H5A H 0.211172 0.609625 0.422863 0.078 Uiso 1 1 calc R U . . .
H5B H 0.291457 0.730978 0.426441 0.078 Uiso 1 1 calc R U . . .
O2 O -0.6040(3) 0.50409(13) 0.10704(10) 0.0750(5) Uani 1 1 d . . . . .
H2 H -0.560730 0.558626 0.084138 0.090 Uiso 1 1 calc R U . . .
C11 C -0.7654(3) 0.43087(18) 0.22333(15) 0.0643(6) Uani 1 1 d . . . . .
H11A H -0.687589 0.367081 0.213189 0.077 Uiso 1 1 calc R U . . .
H11B H -0.774294 0.437041 0.287896 0.077 Uiso 1 1 calc R U . . .
C3 C 0.2529(4) 0.6654(2) 0.62526(15) 0.0696(6) Uani 1 1 d . . . . .
H3A H 0.284419 0.735948 0.654071 0.084 Uiso 1 1 calc R U . . .
H3B H 0.279765 0.607531 0.670272 0.084 Uiso 1 1 calc R U . . .
C4 C 0.3647(4) 0.6477(3) 0.54654(19) 0.0883(8) Uani 1 1 d . . . . .
H4A H 0.407269 0.571736 0.545189 0.106 Uiso 1 1 calc R U . . .
H4B H 0.477125 0.695012 0.552421 0.106 Uiso 1 1 calc R U . . .
C12 C -0.9633(4) 0.4222(2) 0.1691(2) 0.0856(8) Uani 1 1 d . . . . .
H12A H -0.958827 0.376002 0.116035 0.103 Uiso 1 1 calc R U . . .
H12B H -1.053311 0.389960 0.206121 0.103 Uiso 1 1 calc R U . . .
C14 C -0.8538(3) 0.61055(19) 0.16615(18) 0.0706(7) Uani 1 1 d . . . . .
H14A H -0.872058 0.655034 0.218715 0.085 Uiso 1 1 calc R U . . .
H14B H -0.836810 0.659107 0.115851 0.085 Uiso 1 1 calc R U . . .
C13 C -1.0244(4) 0.5352(2) 0.1411(3) 0.0995(10) Uani 1 1 d . . . . .
H13A H -1.131388 0.558066 0.172163 0.119 Uiso 1 1 calc R U . . .
H13B H -1.065101 0.537746 0.076043 0.119 Uiso 1 1 calc R U . . .


_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 1.431(2) . ?
O1 H1 0.8200 . ?
C7 C6 1.195(3) . ?
C7 C8 1.381(3) . ?
C9 C8 1.195(3) . ?
C9 C10 1.472(3) . ?
C2 C3 1.520(3) . ?
C2 C1 1.523(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C10 O2 1.422(2) . ?
C10 C14 1.523(3) . ?
C10 C11 1.523(3) . ?
C1 C6 1.465(3) . ?
C1 C5 1.536(3) . ?
C5 C4 1.503(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
O2 H2 0.8200 . ?
C11 C12 1.514(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C3 C4 1.503(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C12 C13 1.481(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 C13 1.513(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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 H1 109.5 . . ?
C6 C7 C8 178.2(2) . . ?
C8 C9 C10 178.6(2) . . ?
C9 C8 C7 177.0(2) . . ?
C3 C2 C1 104.14(17) . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
O2 C10 C9 109.36(16) . . ?
O2 C10 C14 111.13(17) . . ?
C9 C10 C14 113.29(16) . . ?
O2 C10 C11 106.14(15) . . ?
C9 C10 C11 113.09(16) . . ?
C14 C10 C11 103.52(18) . . ?
O1 C1 C6 110.87(16) . . ?
O1 C1 C2 106.14(15) . . ?
C6 C1 C2 113.94(17) . . ?
O1 C1 C5 111.14(17) . . ?
C6 C1 C5 111.69(16) . . ?
C2 C1 C5 102.68(17) . . ?
C7 C6 C1 176.2(2) . . ?
C4 C5 C1 106.56(18) . . ?
C4 C5 H5A 110.4 . . ?
C1 C5 H5A 110.4 . . ?
C4 C5 H5B 110.4 . . ?
C1 C5 H5B 110.4 . . ?
H5A C5 H5B 108.6 . . ?
C10 O2 H2 109.5 . . ?
C12 C11 C10 104.33(18) . . ?
C12 C11 H11A 110.9 . . ?
C10 C11 H11A 110.9 . . ?
C12 C11 H11B 110.9 . . ?
C10 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
C4 C3 C2 104.33(18) . . ?
C4 C3 H3A 110.9 . . ?
C2 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
C2 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
C3 C4 C5 107.7(2) . . ?
C3 C4 H4A 110.2 . . ?
C5 C4 H4A 110.2 . . ?
C3 C4 H4B 110.2 . . ?
C5 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
C13 C12 C11 107.2(2) . . ?
C13 C12 H12A 110.3 . . ?
C11 C12 H12A 110.3 . . ?
C13 C12 H12B 110.3 . . ?
C11 C12 H12B 110.3 . . ?
H12A C12 H12B 108.5 . . ?
C13 C14 C10 105.79(19) . . ?
C13 C14 H14A 110.6 . . ?
C10 C14 H14A 110.6 . . ?
C13 C14 H14B 110.6 . . ?
C10 C14 H14B 110.6 . . ?
H14A C14 H14B 108.7 . . ?
C12 C13 C14 107.6(2) . . ?
C12 C13 H13A 110.2 . . ?
C14 C13 H13A 110.2 . . ?
C12 C13 H13B 110.2 . . ?
C14 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.038

