# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_tpe_10_hp1
_database_code_depnum_ccdc_archive 'CCDC 2202722'
loop_
_audit_author_name
_audit_author_address
'Stephen Moggach'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2022-08-22 deposited with the CCDC.	2022-09-27 downloaded from the CCDC.
;
_audit_creation_date             2022-08-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_THETM01_tpe_10_hp1          
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The crystal was grown in-situ within a diamond anvil cell
which causes shading of large regions of reciprocal space
and a reduction in resolution.
;
_vrf_PLAT029_tpe_10_hp1          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.609 Why?
RESPONSE: The crystal was grown in-situ within a diamond anvil cell
which causes shading of large regions of reciprocal space
and a reduction in resolution.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H4 O'
_chemical_formula_sum            'C H4 O'
_chemical_formula_weight         32.04
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H20'
_chemical_oxdiff_usercomment     'TPE_as_10 @ 5.094 GPa'
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'

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

_cell_length_a                   4.3989(19)
_cell_length_b                   11.809(16)
_cell_length_c                   10.981(5)
_cell_angle_alpha                90
_cell_angle_beta                 126.69(7)
_cell_angle_gamma                90
_cell_volume                     457.4(8)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    787
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.2140
_cell_measurement_theta_min      4.5890
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             216
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0989
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_Laue_measured_fraction_full 0.609
_diffrn_reflns_Laue_measured_fraction_max 0.609
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1821
_diffrn_reflns_point_group_measured_fraction_full 0.609
_diffrn_reflns_point_group_measured_fraction_max 0.609
_diffrn_reflns_theta_full        19.330
_diffrn_reflns_theta_max         19.330
_diffrn_reflns_theta_min         4.630
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.609
_diffrn_measured_fraction_theta_max 0.609
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      4.00  70.00   0.50   30.00    --   27.00   0.00 150.00  132
  2  ω     -5.00  57.00   0.50   30.00    --   27.00 -53.00  17.00  124
  3  ω    -51.00 -18.00   0.50   30.00    --   27.00 134.00 123.00   66
  4  ω    -30.00  27.00   0.50   30.00    --   27.00  39.00 -12.00  114
  5  ω    -25.00  33.00   0.50   30.00    --   27.00  13.00  -3.00  116
  6  ω      8.00  74.00   0.50   30.00    --   27.00 -97.00-143.00  132
  7  ω    -28.00   4.00   0.50   30.00    --   27.00  97.00 -35.00   64
  8  ω    -57.00   5.00   0.50   30.00    --  -27.00  53.00 -17.00  124
  9  ω    -14.00  15.00   0.50   30.00    --  -27.00 -81.00  29.00   58
 10  ω     -6.00  26.00   0.50   30.00    --  -27.00 -97.00  35.00   64
 11  ω    -22.00  13.00   0.50   30.00    --  -27.00 -53.00  17.00   70
 12  ω     -6.00  27.00   0.50   30.00    --  -27.00 -97.00-143.00   66
 13  ω    -20.00  11.00   0.50   30.00    --   27.00  81.00 151.00   62
 14  ω    -29.00   3.00   0.50   30.00    --   27.00  97.00 -35.00   64
 15  ω     16.00  46.00   0.50   30.00    --   27.00-114.00  44.00   60
 16  ω    -52.00  17.00   0.50   30.00    --  -27.00  39.00 167.00  138
 17  ω    -25.00  29.00   0.50   30.00    --  -27.00 -39.00  12.00  108
 18  ω    -28.00  28.00   0.50   30.00    --  -27.00 -39.00-167.00  112
 19  ω      5.00  39.00   0.50   30.00    --  -27.00-114.00  44.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0325343000
_diffrn_orient_matrix_UB_12      0.0567113000
_diffrn_orient_matrix_UB_13      0.0271396000
_diffrn_orient_matrix_UB_21      0.0368828000
_diffrn_orient_matrix_UB_22      -0.0199844000
_diffrn_orient_matrix_UB_23      0.0684780000
_diffrn_orient_matrix_UB_31      0.1948301000
_diffrn_orient_matrix_UB_32      -0.0054304000
_diffrn_orient_matrix_UB_33      0.0321988000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                181
_reflns_number_total             234
_reflns_odcompleteness_completeness 37.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     23.21
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     31
_refine_ls_number_reflns         234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0858
_refine_ls_restrained_S_all      1.155
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1632P)²+0.2380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2219
_refine_ls_wR_factor_ref         0.2442
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O001) = Uanis(C006) = Uanis(O002) = Uanis(C004) = Uanis(O003) =
Uanis(C005)
3.a Idealised Me refined as rotating group:
 C004(H00D,H00E,H00F), C005(H00G,H00H,H00I), C006(H00A,H00B,H00C)
3.b Idealised tetrahedral OH refined as rotating group:
 O001(H001), O002(H002), O003(H003)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O001 O 0.0816(14) 0.5999(8) 0.4373(5) 0.066(3) Uani 1 1 d . . . . .
H001 H -0.111064 0.630551 0.365432 0.099 Uiso 1 1 calc R U . . .
O002 O 0.5196(12) 0.7985(11) 0.6816(6) 0.066(3) Uani 1 1 d . . . . .
H002 H 0.513932 0.738988 0.718709 0.099 Uiso 1 1 calc R U . . .
O003 O 0.4003(14) 0.5903(9) 0.7372(6) 0.066(3) Uani 1 1 d . . . . .
H003 H 0.273481 0.553627 0.658268 0.099 Uiso 1 1 calc R U . . .
C004 C 0.141(2) 0.8452(12) 0.5833(9) 0.066(3) Uani 1 1 d . . . . .
H00D H 0.013167 0.814475 0.482998 0.099 Uiso 1 1 calc R U . . .
H00E H 0.155424 0.926111 0.579346 0.099 Uiso 1 1 calc R U . . .
H00F H 0.001756 0.826106 0.622433 0.099 Uiso 1 1 calc R U . . .
C005 C 0.258(2) 0.5743(14) 0.8204(10) 0.066(3) Uani 1 1 d . . . . .
H00G H 0.019754 0.612704 0.770985 0.099 Uiso 1 1 calc R U . . .
H00H H 0.434502 0.604450 0.920798 0.099 Uiso 1 1 calc R U . . .
H00I H 0.223456 0.494888 0.826648 0.099 Uiso 1 1 calc R U . . .
C006 C 0.398(2) 0.6296(15) 0.4364(9) 0.066(3) Uani 1 1 d . . . . .
H00A H 0.346731 0.700046 0.383750 0.099 Uiso 1 1 calc R U . . .
H00B H 0.436186 0.571265 0.385764 0.099 Uiso 1 1 calc R U . . .
H00C H 0.622313 0.637078 0.538933 0.099 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
O001 H001 0.8200 . ?
O001 C006 1.442(11) . ?
O002 H002 0.8200 . ?
O002 C004 1.449(10) . ?
O003 H003 0.8200 . ?
O003 C005 1.393(9) . ?
C004 H00D 0.9600 . ?
C004 H00E 0.9600 . ?
C004 H00F 0.9600 . ?
C005 H00G 0.9600 . ?
C005 H00H 0.9600 . ?
C005 H00I 0.9600 . ?
C006 H00A 0.9600 . ?
C006 H00B 0.9600 . ?
C006 H00C 0.9600 . ?

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
C006 O001 H001 109.5 . . ?
C004 O002 H002 109.5 . . ?
C005 O003 H003 109.5 . . ?
O002 C004 H00D 109.5 . . ?
O002 C004 H00E 109.5 . . ?
O002 C004 H00F 109.5 . . ?
H00D C004 H00E 109.5 . . ?
H00D C004 H00F 109.5 . . ?
H00E C004 H00F 109.5 . . ?
O003 C005 H00G 109.5 . . ?
O003 C005 H00H 109.5 . . ?
O003 C005 H00I 109.5 . . ?
H00G C005 H00H 109.5 . . ?
H00G C005 H00I 109.5 . . ?
H00H C005 H00I 109.5 . . ?
O001 C006 H00A 109.5 . . ?
O001 C006 H00B 109.5 . . ?
O001 C006 H00C 109.5 . . ?
H00A C006 H00B 109.5 . . ?
H00A C006 H00C 109.5 . . ?
H00B C006 H00C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.529
_oxdiff_exptl_absorpt_empirical_full_min 0.476
