# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_m20170616a1
_database_code_depnum_ccdc_archive 'CCDC 1571756'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2018-01-18 downloaded from the CCDC.
;
_audit_creation_date             2017-08-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C9 H12 O2'
_chemical_formula_sum            'C9 H12 O2'
_chemical_formula_weight         152.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   20.7040(19)
_cell_length_b                   20.7040(19)
_cell_length_c                   7.2027(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3087.5(6)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    3865
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.6
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.9820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15061
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.527
_diffrn_reflns_theta_min         3.584
_diffrn_ambient_temperature      133.15
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1494
_reflns_number_total             1755
_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       'CrystalClear-SM Expert 2.1 b42'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1755
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0423P)²+1.9603P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0892
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O1 O 0.63009(4) 0.63352(4) 0.11284(12) 0.0245(2) Uani 1 1 d . . . . .
O2 O 0.75896(4) 0.56812(4) 0.03860(11) 0.02319(19) Uani 1 1 d . . . . .
H2 H 0.7765 0.5460 0.1225 0.035 Uiso 1 1 calc GR . . . .
C1 C 0.68842(5) 0.63869(5) 0.22389(15) 0.0187(2) Uani 1 1 d . . . . .
C2 C 0.68421(6) 0.61187(5) 0.41606(16) 0.0252(2) Uani 1 1 d . . . . .
H2A H 0.7266 0.6168 0.4779 0.030 Uiso 1 1 calc R . . . .
H2B H 0.6744 0.5651 0.4088 0.030 Uiso 1 1 calc R . . . .
C3 C 0.63341(6) 0.64454(6) 0.53109(18) 0.0293(3) Uani 1 1 d . . . . .
H3 H 0.6234 0.6262 0.6485 0.035 Uiso 1 1 calc R . . . .
C4 C 0.60158(6) 0.69713(6) 0.48063(19) 0.0308(3) Uani 1 1 d . . . . .
H4 H 0.5707 0.7139 0.5655 0.037 Uiso 1 1 calc R . . . .
C5 C 0.61019(5) 0.73239(5) 0.30061(18) 0.0280(3) Uani 1 1 d . . . . .
H5A H 0.5674 0.7387 0.2421 0.034 Uiso 1 1 calc R . . . .
H5B H 0.6287 0.7756 0.3260 0.034 Uiso 1 1 calc R . . . .
C6 C 0.65336(5) 0.69716(5) 0.16793(16) 0.0221(2) Uani 1 1 d . . . . .
C7 C 0.68938(6) 0.73014(5) 0.01245(17) 0.0295(3) Uani 1 1 d . . . . .
H7A H 0.7133 0.7683 0.0588 0.035 Uiso 1 1 calc R . . . .
H7B H 0.6594 0.7441 -0.0868 0.035 Uiso 1 1 calc R . . . .
C8 C 0.73616(6) 0.67802(6) -0.05907(17) 0.0288(3) Uani 1 1 d . . . . .
H8A H 0.7168 0.6543 -0.1646 0.035 Uiso 1 1 calc R . . . .
H8B H 0.7772 0.6979 -0.1007 0.035 Uiso 1 1 calc R . . . .
C9 C 0.74814(5) 0.63227(5) 0.10493(15) 0.0207(2) Uani 1 1 d . . . . .
H9 H 0.7867 0.6472 0.1765 0.025 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4523(12) . ?
O1 C6 1.4580(12) . ?
O2 H2 0.8400 . ?
O2 C9 1.4292(12) . ?
C1 C2 1.4939(15) . ?
C1 C6 1.4678(14) . ?
C1 C9 1.5103(14) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5000(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3235(17) . ?
C4 H4 0.9500 . ?
C4 C5 1.4986(18) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.4980(16) . ?
C6 C7 1.5088(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5387(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5342(15) . ?
C9 H9 1.0000 . ?

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 C6 60.57(6) . . ?
C9 O2 H2 109.5 . . ?
O1 C1 C2 115.74(9) . . ?
O1 C1 C6 59.90(6) . . ?
O1 C1 C9 111.21(9) . . ?
C2 C1 C9 122.73(9) . . ?
C6 C1 C2 122.15(10) . . ?
C6 C1 C9 108.76(9) . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C1 C2 C3 112.64(9) . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C2 C3 H3 117.7 . . ?
C4 C3 C2 124.63(11) . . ?
C4 C3 H3 117.7 . . ?
C3 C4 H4 117.3 . . ?
C3 C4 C5 125.39(11) . . ?
C5 C4 H4 117.3 . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 C4 112.69(9) . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
O1 C6 C1 59.52(6) . . ?
O1 C6 C5 114.62(9) . . ?
O1 C6 C7 111.73(9) . . ?
C1 C6 C5 121.42(10) . . ?
C1 C6 C7 109.43(9) . . ?
C5 C6 C7 123.23(9) . . ?
C6 C7 H7A 111.0 . . ?
C6 C7 H7B 111.0 . . ?
C6 C7 C8 104.02(9) . . ?
H7A C7 H7B 109.0 . . ?
C8 C7 H7A 111.0 . . ?
C8 C7 H7B 111.0 . . ?
C7 C8 H8A 110.5 . . ?
C7 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
C9 C8 C7 106.08(9) . . ?
C9 C8 H8A 110.5 . . ?
C9 C8 H8B 110.5 . . ?
O2 C9 C1 113.57(8) . . ?
O2 C9 C8 109.98(9) . . ?
O2 C9 H9 109.6 . . ?
C1 C9 C8 104.48(8) . . ?
C1 C9 H9 109.6 . . ?
C8 C9 H9 109.6 . . ?

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
O2 H2 O2 0.84 1.86 2.6999(8) 173.9 8_454

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 -60.23(12) . . . . ?
O1 C1 C6 C5 101.93(11) . . . . ?
O1 C1 C6 C7 -104.36(10) . . . . ?
O1 C1 C9 O2 -71.79(10) . . . . ?
O1 C1 C9 C8 48.05(10) . . . . ?
O1 C6 C7 C8 -47.69(12) . . . . ?
C1 O1 C6 C5 -113.32(11) . . . . ?
C1 O1 C6 C7 100.42(10) . . . . ?
C1 C2 C3 C4 -9.01(17) . . . . ?
C1 C6 C7 C8 16.31(12) . . . . ?
C2 C1 C6 O1 -103.22(11) . . . . ?
C2 C1 C6 C5 -1.28(15) . . . . ?
C2 C1 C6 C7 152.42(10) . . . . ?
C2 C1 C9 O2 71.65(12) . . . . ?
C2 C1 C9 C8 -168.51(10) . . . . ?
C2 C3 C4 C5 0.7(2) . . . . ?
C3 C4 C5 C6 7.47(17) . . . . ?
C4 C5 C6 O1 61.15(13) . . . . ?
C4 C5 C6 C1 -6.89(15) . . . . ?
C4 C5 C6 C7 -156.93(11) . . . . ?
C5 C6 C7 C8 169.44(10) . . . . ?
C6 O1 C1 C2 113.79(11) . . . . ?
C6 O1 C1 C9 -100.01(9) . . . . ?
C6 C1 C2 C3 9.00(14) . . . . ?
C6 C1 C9 O2 -135.92(9) . . . . ?
C6 C1 C9 C8 -16.08(11) . . . . ?
C6 C7 C8 C9 -25.99(12) . . . . ?
C7 C8 C9 O2 148.22(9) . . . . ?
C7 C8 C9 C1 25.99(11) . . . . ?
C9 C1 C2 C3 157.83(10) . . . . ?
C9 C1 C6 O1 104.17(9) . . . . ?
C9 C1 C6 C5 -153.90(10) . . . . ?
C9 C1 C6 C7 -0.20(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
