# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_p167
_audit_block_doi                 10.5517/ccdc.csd.cc27j6cc
_database_code_depnum_ccdc_archive 'CCDC 2071152'
loop_
_audit_author_name
_audit_author_address
'Vincent Lynch'
;University of Texas at Austin
United States of America
;
_audit_update_record             
;
2021-03-17 deposited with the CCDC.	2021-08-05 downloaded from the CCDC.
;
_audit_creation_date             2021-02-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H14 O3'
_chemical_formula_sum            'C9 H14 O3'
_chemical_formula_weight         170.20
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C9H14O3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.60780(15)
_cell_length_b                   9.1979(2)
_cell_length_c                   13.39653(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     937.43(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6284
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      73.1310
_cell_measurement_theta_min      5.8170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.269
_exptl_absorpt_correction_type   'gaussian and multi-scan'
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.2795
0 0 1 0.2795
1 1 0 0.0439
-1 -1 0 0.0669
-3 4 -1 0.0880
3 -4 1 0.0300
3 5 0 0.0589
-3 -5 0 0.0699

_exptl_crystal_size_max          0.574
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.111
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0008 0.0012 -0.9999 -0.0197 0.1132 0.0034
0.0008 -0.0012 0.9999 0.0197 -0.1132 -0.0034
1.0012 0.9962 0.0026 0.0788 0.0060 0.2503
-1.0012 -0.9962 -0.0026 -0.0788 -0.0060 -0.2503
-3.4021 4.2895 -0.8209 -0.9705 -0.0771 0.2286
3.4021 -4.2895 0.8209 0.9705 0.0771 -0.2286
3.0085 4.9865 0.0160 0.0587 -0.0213 1.0318
-3.0085 -4.9865 -0.0160 -0.0587 0.0213 -1.0318

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8913
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.267
_diffrn_reflns_theta_min         5.835
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2940
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -129.00  47.00   1.00    4.00    --  -41.34   0.00-120.00  176
  2  ω     27.00  97.00   1.00    4.00    --   41.34-125.00-180.00   70
  3  ω     97.00 178.00   1.00   13.00    --  107.09 125.00  60.00   81
  4  ω     34.00 133.00   1.00   13.00    --  107.09 -45.00 150.00   99
  5  ω    103.00 178.00   1.00   13.00    --  107.09  77.00  90.00   75
  6  ω     97.00 178.00   1.00   13.00    --  107.09 125.00 -60.00   81
  7  ω    103.00 178.00   1.00   13.00    --  107.09  77.00 150.00   75
  8  ω    103.00 178.00   1.00   13.00    --  107.09  77.00-180.00   75
  9  ω     24.00 107.00   1.00   13.00    --  107.09 -94.00  90.00   83
 10  ω   -113.00 -13.00   1.00    4.00    --  -41.34 -57.00 150.00  100
 11  ω   -113.00 -13.00   1.00    4.00    --  -41.34 -57.00  60.00  100
 12  ω     81.00 178.00   1.00   13.00    --  107.09  45.00 -90.00   97
 13  ω     54.00 178.00   1.00   13.00    --  107.09  15.00 150.00  124
 14  ω     78.00 178.00   1.00   13.00    --  107.09  61.00 -60.00  100
 15  ω     79.00 178.00   1.00   13.00    --  107.09  30.00  30.00   99
 16  ω   -113.00 -13.00   1.00    4.00    --  -41.34 -57.00-120.00  100
 17  ω    -87.00  -6.00   1.00    4.00    --  -41.34 125.00 -90.00   81
 18  ω     78.00 109.00   1.00   13.00    --  107.09  61.00-150.00   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1677343000
_diffrn_orient_matrix_UB_12      -0.0894838000
_diffrn_orient_matrix_UB_13      0.0194619000
_diffrn_orient_matrix_UB_21      0.0255875000
_diffrn_orient_matrix_UB_22      -0.0193517000
_diffrn_orient_matrix_UB_23      -0.1132875000
_diffrn_orient_matrix_UB_31      0.1104783000
_diffrn_orient_matrix_UB_32      0.1402848000
_diffrn_orient_matrix_UB_33      -0.0032849000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                1831
_reflns_number_total             1862
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.70a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.70a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Shelxtl-Plus/XP, Bruker AXS, Inc. 2009'
_computing_publication_material  'Shlelxtl-Plus, Bruker AXS, Inc. 2009'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 735 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         1862
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      1.127
_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)+(0.0416P)²+0.1297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0738
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
O1 O 0.28350(14) 0.61962(11) 0.46678(7) 0.0198(2) Uani 1 1 d . . . . .
O2 O 0.25401(15) 0.40629(11) 0.53765(7) 0.0235(3) Uani 1 1 d . . . . .
O3 O 0.16168(16) 0.43639(12) 0.19449(8) 0.0258(3) Uani 1 1 d . . . . .
H3 H 0.191(4) 0.495(3) 0.143(2) 0.057(7) Uiso 1 1 d . . . . .
C1 C 0.2392(2) 0.47883(16) 0.46070(10) 0.0188(3) Uani 1 1 d . . . . .
C2 C 0.18304(19) 0.41658(16) 0.36672(11) 0.0194(3) Uani 1 1 d . . . . .
C3 C 0.20004(19) 0.49668(16) 0.28250(10) 0.0191(3) Uani 1 1 d . . . . .
C4 C 0.2707(2) 0.64989(16) 0.28458(10) 0.0192(3) Uani 1 1 d . . . . .
H4 H 0.206107 0.707148 0.232823 0.023 Uiso 1 1 calc R U . . .
C5 C 0.2281(2) 0.71612(15) 0.38621(10) 0.0184(3) Uani 1 1 d . . . . .
H5 H 0.097902 0.729301 0.390825 0.022 Uiso 1 1 calc R U . . .
C6 C 0.1270(2) 0.26014(17) 0.36768(11) 0.0242(3) Uani 1 1 d . . . . .
H6A H 0.218124 0.201168 0.399824 0.036 Uiso 1 1 calc R U . . .
H6B H 0.109567 0.226469 0.298987 0.036 Uiso 1 1 calc R U . . .
H6C H 0.016644 0.250629 0.404867 0.036 Uiso 1 1 calc R U . . .
C7 C 0.4665(2) 0.65030(18) 0.25624(11) 0.0247(3) Uani 1 1 d . . . . .
H7A H 0.533524 0.596345 0.306533 0.037 Uiso 1 1 calc R U . . .
H7B H 0.509119 0.750740 0.253231 0.037 Uiso 1 1 calc R U . . .
H7C H 0.481582 0.604076 0.190895 0.037 Uiso 1 1 calc R U . . .
C8 C 0.3150(2) 0.86101(17) 0.40749(11) 0.0221(3) Uani 1 1 d . . . . .
H8A H 0.285564 0.929885 0.353222 0.026 Uiso 1 1 calc R U . . .
H8B H 0.444151 0.847829 0.407782 0.026 Uiso 1 1 calc R U . . .
C9 C 0.2581(2) 0.92644(17) 0.50725(11) 0.0249(3) Uani 1 1 d . . . . .
H9A H 0.131300 0.945244 0.505987 0.037 Uiso 1 1 calc R U . . .
H9B H 0.321180 1.017876 0.518475 0.037 Uiso 1 1 calc R U . . .
H9C H 0.285238 0.858164 0.561245 0.037 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 1.3405(18) . ?
O1 C5 1.4596(16) . ?
O2 C1 1.2331(18) . ?
O3 H3 0.90(3) . ?
O3 C3 1.3353(17) . ?
C1 C2 1.4476(19) . ?
C2 C3 1.354(2) . ?
C2 C6 1.501(2) . ?
C3 C4 1.509(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.5263(18) . ?
C4 C7 1.537(2) . ?
C5 H5 1.0000 . ?
C5 C8 1.515(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5283(19) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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 C5 118.03(11) . . ?
C3 O3 H3 112.0(17) . . ?
O1 C1 C2 120.61(12) . . ?
O2 C1 O1 116.67(13) . . ?
O2 C1 C2 122.68(13) . . ?
C1 C2 C6 117.11(13) . . ?
C3 C2 C1 118.77(13) . . ?
C3 C2 C6 123.79(13) . . ?
O3 C3 C2 119.28(13) . . ?
O3 C3 C4 118.82(12) . . ?
C2 C3 C4 121.81(13) . . ?
C3 C4 H4 107.7 . . ?
C3 C4 C5 108.27(11) . . ?
C3 C4 C7 110.07(12) . . ?
C5 C4 H4 107.7 . . ?
C5 C4 C7 115.16(12) . . ?
C7 C4 H4 107.7 . . ?
O1 C5 C4 110.83(11) . . ?
O1 C5 H5 108.3 . . ?
O1 C5 C8 105.66(11) . . ?
C4 C5 H5 108.3 . . ?
C8 C5 C4 115.24(12) . . ?
C8 C5 H5 108.3 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.0 . . ?
C5 C8 H8B 109.0 . . ?
C5 C8 C9 112.80(13) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O2 0.90(3) 1.73(3) 2.6305(15) 175(3) 2_564 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 9.4(2) . . . . ?
O1 C1 C2 C6 -176.92(13) . . . . ?
O1 C5 C8 C9 -61.03(15) . . . . ?
O2 C1 C2 C3 -168.37(14) . . . . ?
O2 C1 C2 C6 5.3(2) . . . . ?
O3 C3 C4 C5 155.29(13) . . . . ?
O3 C3 C4 C7 -78.02(16) . . . . ?
C1 O1 C5 C4 -47.87(16) . . . . ?
C1 O1 C5 C8 -173.35(12) . . . . ?
C1 C2 C3 O3 174.77(13) . . . . ?
C1 C2 C3 C4 -1.8(2) . . . . ?
C2 C3 C4 C5 -28.11(18) . . . . ?
C2 C3 C4 C7 98.57(16) . . . . ?
C3 C4 C5 O1 50.63(15) . . . . ?
C3 C4 C5 C8 170.53(12) . . . . ?
C4 C5 C8 C9 176.26(13) . . . . ?
C5 O1 C1 O2 -165.22(12) . . . . ?
C5 O1 C1 C2 16.85(19) . . . . ?
C6 C2 C3 O3 1.6(2) . . . . ?
C6 C2 C3 C4 -175.00(13) . . . . ?
C7 C4 C5 O1 -73.04(15) . . . . ?
C7 C4 C5 C8 46.86(17) . . . . ?

_olex2_date_sample_data_collection 2021-02-09
_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 1.772
_oxdiff_exptl_absorpt_empirical_full_min 0.684
####################################################################### 
# 
# 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_p127
_audit_block_doi                 10.5517/ccdc.csd.cc27j6dd
_database_code_depnum_ccdc_archive 'CCDC 2071153'
loop_
_audit_author_name
_audit_author_address
'Vincent Lynch'
;University of Texas at Austin
United States of America
;
_audit_update_record             
;
2021-03-17 deposited with the CCDC.	2021-08-05 downloaded from the CCDC.
;
_audit_creation_date             2021-03-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H14 O3'
_chemical_formula_sum            'C9 H14 O3'
_chemical_formula_weight         170.20
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C9H14O3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.6080(2)
_cell_length_b                   9.2035(3)
_cell_length_c                   13.3936(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     937.83(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6196
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      73.2220
_cell_measurement_theta_min      4.8020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.515
_exptl_absorpt_correction_type   'gaussian and multi-scan'
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -4 0 0.0475
-4 4 0 0.0475
-3 -4 0 0.0831
3 4 0 0.0831
0 -1 9 0.2031
0 1 -9 0.2031
3 3 6 0.1239
3 4 -3 0.1277
-3 -4 3 0.1277
-2 5 3 0.0791

_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.095
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.7398 -3.9031 0.1138 -0.9996 0.0257 -0.0091
-3.7398 3.9031 -0.1138 0.9996 -0.0257 0.0091
-3.2647 -4.4827 -0.2615 0.0161 -0.1911 -0.9814
3.2647 4.4827 0.2615 -0.0161 0.1911 0.9814
0.2333 -0.5044 8.6466 -0.0773 0.9776 -0.1960
-0.2333 0.5044 -8.6466 0.0773 -0.9776 0.1960
2.7187 3.2232 5.5524 -0.0605 0.7551 0.6528
2.8488 4.2628 -3.4449 0.0184 -0.2436 0.9697
-2.8488 -4.2628 3.4449 -0.0184 0.2436 -0.9697
-1.7147 5.3276 2.5536 0.8464 0.3515 0.4001

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8913
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.337
_diffrn_reflns_theta_min         5.833
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2940
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00   1.00   1.00    3.00    --  -39.84 -19.00  90.00  121
  2  ω     61.00 129.00   1.00    3.00    --   39.84 178.00  90.00   68
  3  ω     61.00 129.00   1.00    3.00    --   39.84 178.00   0.00   68
  4  ω    103.00 178.00   1.00   11.00    --  107.09  77.00 -30.00   75
  5  ω    103.00 178.00   1.00   11.00    --  107.09  77.00-120.00   75
  6  ω    103.00 178.00   1.00   11.00    --  107.09  77.00 -60.00   75
  7  ω     81.00 178.00   1.00   11.00    --  107.09  45.00  30.00   97
  8  ω     34.00 112.00   1.00   11.00    --  107.09-125.00  30.00   78
  9  ω     35.00 136.00   1.00   11.00    --  107.09 -61.00-150.00  101
 10  ω    -64.00  34.00   1.00    3.00    --  -39.84  38.00  90.00   98
 11  ω   -114.00 -15.00   1.00    3.00    --  -39.84 -38.00   0.00   99
 12  ω   -113.00 -10.00   1.00    3.00    --  -39.84 -67.00 -75.00  103
 13  ω     24.00 107.00   1.00   11.00    --  107.09 -94.00  90.00   83
 14  ω     79.00 178.00   1.00   11.00    --  107.09  30.00 120.00   99
 15  ω     54.00 178.00   1.00   11.00    --  107.09  15.00 -60.00  124
 16  ω     78.00 178.00   1.00   11.00    --  107.09  61.00 150.00  100
 17  ω     78.00 178.00   1.00   11.00    --  107.09  61.00  60.00  100
 18  ω     78.00 178.00   1.00   11.00    --  107.09  61.00-180.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1540742000
_diffrn_orient_matrix_UB_12      0.1085300000
_diffrn_orient_matrix_UB_13      0.0015540000
_diffrn_orient_matrix_UB_21      0.0232893000
_diffrn_orient_matrix_UB_22      0.0190494000
_diffrn_orient_matrix_UB_23      0.1135403000
_diffrn_orient_matrix_UB_31      0.1294174000
_diffrn_orient_matrix_UB_32      0.1257819000
_diffrn_orient_matrix_UB_33      -0.0188201000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                1829
_reflns_number_total             1869
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.70a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.70a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Shelxtl-Plus/XP, Bruker AXS, Inc. 2009'
_computing_publication_material  'Shelxtl-Plus, Bruker AXS, Inc. 2009'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 736 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         1869
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0300
_refine_ls_restrained_S_all      1.112
_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)+(0.0471P)²+0.1267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0797
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.28352(15) 0.61954(12) 0.53317(7) 0.0209(3) Uani 1 1 d . . . . .
O2 O 0.25407(16) 0.40635(12) 0.46231(8) 0.0251(3) Uani 1 1 d . . . . .
O3 O 0.16161(18) 0.43641(13) 0.80552(8) 0.0273(3) Uani 1 1 d . . . . .
H3 H 0.193(4) 0.493(3) 0.858(2) 0.062(8) Uiso 1 1 d . . . . .
C1 C 0.2392(2) 0.47890(18) 0.53926(11) 0.0198(3) Uani 1 1 d . . . . .
C2 C 0.1829(2) 0.41648(17) 0.63321(11) 0.0206(3) Uani 1 1 d . . . . .
C3 C 0.2002(2) 0.49667(17) 0.71763(11) 0.0202(3) Uani 1 1 d . . . . .
C4 C 0.2709(2) 0.64963(17) 0.71543(10) 0.0205(3) Uani 1 1 d . . . . .
H4 H 0.206301 0.706786 0.767261 0.025 Uiso 1 1 calc R U . . .
C5 C 0.2279(2) 0.71619(16) 0.61380(10) 0.0197(3) Uani 1 1 d . . . . .
H5 H 0.097649 0.729394 0.609217 0.024 Uiso 1 1 calc R U . . .
C6 C 0.1271(2) 0.26019(18) 0.63221(12) 0.0256(4) Uani 1 1 d . . . . .
H6A H 0.016306 0.250741 0.595424 0.038 Uiso 1 1 calc R U . . .
H6B H 0.110493 0.226300 0.700933 0.038 Uiso 1 1 calc R U . . .
H6C H 0.217883 0.201431 0.599624 0.038 Uiso 1 1 calc R U . . .
C7 C 0.4665(2) 0.65031(19) 0.74376(12) 0.0263(4) Uani 1 1 d . . . . .
H7A H 0.533614 0.596256 0.693549 0.039 Uiso 1 1 calc R U . . .
H7B H 0.481669 0.604366 0.809199 0.039 Uiso 1 1 calc R U . . .
H7C H 0.509026 0.750734 0.746594 0.039 Uiso 1 1 calc R U . . .
C8 C 0.3151(2) 0.86095(18) 0.59259(11) 0.0233(4) Uani 1 1 d . . . . .
H8A H 0.444235 0.847613 0.592237 0.028 Uiso 1 1 calc R U . . .
H8B H 0.285849 0.929807 0.646888 0.028 Uiso 1 1 calc R U . . .
C9 C 0.2580(2) 0.92629(18) 0.49279(12) 0.0262(4) Uani 1 1 d . . . . .
H9A H 0.286215 0.858452 0.438718 0.039 Uiso 1 1 calc R U . . .
H9B H 0.320191 1.018173 0.481826 0.039 Uiso 1 1 calc R U . . .
H9C H 0.131042 0.944141 0.493856 0.039 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 1.340(2) . ?
O1 C5 1.4618(17) . ?
O2 C1 1.2332(19) . ?
O3 H3 0.91(3) . ?
O3 C3 1.3339(18) . ?
C1 C2 1.448(2) . ?
C2 C3 1.357(2) . ?
C2 C6 1.500(2) . ?
C3 C4 1.507(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.5280(19) . ?
C4 C7 1.536(2) . ?
C5 H5 1.0000 . ?
C5 C8 1.515(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.529(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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 C5 118.03(11) . . ?
C3 O3 H3 112.6(19) . . ?
O1 C1 C2 120.69(13) . . ?
O2 C1 O1 116.68(13) . . ?
O2 C1 C2 122.59(14) . . ?
C1 C2 C6 117.16(14) . . ?
C3 C2 C1 118.68(14) . . ?
C3 C2 C6 123.82(14) . . ?
O3 C3 C2 119.21(14) . . ?
O3 C3 C4 118.96(13) . . ?
C2 C3 C4 121.75(13) . . ?
C3 C4 H4 107.6 . . ?
C3 C4 C5 108.39(12) . . ?
C3 C4 C7 110.16(13) . . ?
C5 C4 H4 107.6 . . ?
C5 C4 C7 115.21(13) . . ?
C7 C4 H4 107.6 . . ?
O1 C5 C4 110.62(12) . . ?
O1 C5 H5 108.4 . . ?
O1 C5 C8 105.64(12) . . ?
C4 C5 H5 108.4 . . ?
C8 C5 C4 115.19(13) . . ?
C8 C5 H5 108.4 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.1 . . ?
C5 C8 H8B 109.1 . . ?
C5 C8 C9 112.66(13) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O2 0.91(3) 1.72(3) 2.6298(16) 176(3) 2_565 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -9.5(2) . . . . ?
O1 C1 C2 C6 176.98(14) . . . . ?
O1 C5 C8 C9 61.19(16) . . . . ?
O2 C1 C2 C3 168.28(15) . . . . ?
O2 C1 C2 C6 -5.3(2) . . . . ?
O3 C3 C4 C5 -155.06(14) . . . . ?
O3 C3 C4 C7 78.05(17) . . . . ?
C1 O1 C5 C4 47.98(18) . . . . ?
C1 O1 C5 C8 173.26(13) . . . . ?
C1 C2 C3 O3 -174.85(14) . . . . ?
C1 C2 C3 C4 1.9(2) . . . . ?
C2 C3 C4 C5 28.2(2) . . . . ?
C2 C3 C4 C7 -98.67(17) . . . . ?
C3 C4 C5 O1 -50.78(16) . . . . ?
C3 C4 C5 C8 -170.47(13) . . . . ?
C4 C5 C8 C9 -176.41(14) . . . . ?
C5 O1 C1 O2 165.17(13) . . . . ?
C5 O1 C1 C2 -16.9(2) . . . . ?
C6 C2 C3 O3 -1.8(2) . . . . ?
C6 C2 C3 C4 174.93(14) . . . . ?
C7 C4 C5 O1 73.13(17) . . . . ?
C7 C4 C5 C8 -46.56(18) . . . . ?

_olex2_date_sample_data_collection 2021-03-10
_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 1.228
_oxdiff_exptl_absorpt_empirical_full_min 0.802
