# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_qrh008_0m
_database_code_depnum_ccdc_archive 'CCDC 1854579'
_audit_update_record             
;
2018-07-09 deposited with the CCDC.	2019-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 O2'
_chemical_formula_weight         224.25

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.6376(9)
_cell_length_b                   8.3094(8)
_cell_length_c                   14.8885(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.0420(10)
_cell_angle_gamma                90.00
_cell_volume                     1191.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2524
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      27.22

_exptl_crystal_description       lump
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      1.250
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9813
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_process_details   SADDAB

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5269
_diffrn_reflns_av_R_equivalents  0.0140
_diffrn_reflns_av_sigmaI/netI    0.0150
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2065
_reflns_number_gt                1731
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0568P)²+0.1809P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2065
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1111
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.36512(13) 0.19294(16) 0.82895(8) 0.0798(4) Uani 1 1 d . . .
O2 O 0.49307(11) 0.16898(12) 0.95545(6) 0.0587(3) Uani 1 1 d . . .
C15 C 0.91316(19) 0.5673(3) 1.10703(14) 0.0962(7) Uani 1 1 d . . .
H15A H 0.8732 0.6327 1.1526 0.144 Uiso 1 1 calc R . .
H15B H 0.9482 0.6352 1.0609 0.144 Uiso 1 1 calc R . .
H15C H 0.9878 0.5045 1.1333 0.144 Uiso 1 1 calc R . .
C5 C 0.80320(15) 0.4561(2) 1.06664(10) 0.0618(4) Uani 1 1 d . . .
C4 C 0.73417(14) 0.49502(18) 0.98547(9) 0.0533(4) Uani 1 1 d . . .
H4 H 0.7571 0.5883 0.9548 0.064 Uiso 1 1 calc R . .
C3 C 0.63175(13) 0.39431(16) 0.95097(8) 0.0433(3) Uani 1 1 d . . .
C2 C 0.53680(13) 0.40289(16) 0.86919(8) 0.0442(3) Uani 1 1 d . . .
H2 H 0.4733 0.4937 0.8767 0.053 Uiso 1 1 calc R . .
C9 C 0.59966(14) 0.41810(15) 0.77772(8) 0.0462(3) Uani 1 1 d . . .
C10 C 0.52544(18) 0.49217(19) 0.70833(10) 0.0623(4) Uani 1 1 d . . .
H10 H 0.4383 0.5353 0.7182 0.075 Uiso 1 1 calc R . .
C11 C 0.5811(2) 0.5022(2) 0.62373(11) 0.0815(6) Uani 1 1 d . . .
H11 H 0.5308 0.5521 0.5771 0.098 Uiso 1 1 calc R . .
C12 C 0.7091(2) 0.4393(2) 0.60830(11) 0.0827(6) Uani 1 1 d . . .
H12 H 0.7457 0.4461 0.5515 0.099 Uiso 1 1 calc R . .
C14 C 0.72905(17) 0.3554(2) 0.76152(11) 0.0655(4) Uani 1 1 d . . .
H14 H 0.7803 0.3055 0.8077 0.079 Uiso 1 1 calc R . .
C13 C 0.7829(2) 0.3664(2) 0.67681(13) 0.0829(6) Uani 1 1 d . . .
H13 H 0.8701 0.3238 0.6665 0.100 Uiso 1 1 calc R . .
C1 C 0.45379(15) 0.24773(19) 0.87781(9) 0.0542(4) Uani 1 1 d . . .
C8 C 0.59970(14) 0.25725(17) 0.99793(9) 0.0486(3) Uani 1 1 d . . .
C7 C 0.66578(17) 0.21294(19) 1.07723(10) 0.0618(4) Uani 1 1 d . . .
H7 H 0.6429 0.1188 1.1071 0.074 Uiso 1 1 calc R . .
C6 C 0.76784(17) 0.3152(2) 1.11032(10) 0.0665(5) Uani 1 1 d . . .
H6 H 0.8148 0.2888 1.1640 0.080 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 1.1926(17) . ?
O2 C1 1.3698(17) . ?
O2 C8 1.3956(17) . ?
C15 C5 1.514(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C5 C6 1.388(2) . ?
C5 C4 1.397(2) . ?
C4 C3 1.3792(19) . ?
C4 H4 0.9300 . ?
C3 C8 1.3772(19) . ?
C3 C2 1.4985(18) . ?
C2 C9 1.5154(17) . ?
C2 C1 1.525(2) . ?
C2 H2 0.9800 . ?
C9 C10 1.380(2) . ?
C9 C14 1.381(2) . ?
C10 C11 1.389(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(3) . ?
C12 H12 0.9300 . ?
C14 C13 1.384(2) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C8 C7 1.3716(19) . ?
C7 C6 1.378(2) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?

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 O2 C8 107.95(11) . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C6 C5 C4 118.92(14) . . ?
C6 C5 C15 120.58(16) . . ?
C4 C5 C15 120.49(17) . . ?
C3 C4 C5 119.62(14) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C8 C3 C4 118.89(13) . . ?
C8 C3 C2 108.08(11) . . ?
C4 C3 C2 133.00(12) . . ?
C3 C2 C9 118.82(11) . . ?
C3 C2 C1 101.44(10) . . ?
C9 C2 C1 111.95(11) . . ?
C3 C2 H2 108.0 . . ?
C9 C2 H2 108.0 . . ?
C1 C2 H2 108.0 . . ?
C10 C9 C14 118.99(13) . . ?
C10 C9 C2 119.79(13) . . ?
C14 C9 C2 121.20(12) . . ?
C9 C10 C11 119.91(17) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.66(17) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 119.57(16) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C9 C14 C13 120.31(16) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C12 C13 C14 120.56(18) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
O1 C1 O2 120.19(14) . . ?
O1 C1 C2 129.64(14) . . ?
O2 C1 C2 110.17(11) . . ?
C7 C8 C3 123.59(14) . . ?
C7 C8 O2 124.11(13) . . ?
C3 C8 O2 112.30(11) . . ?
C8 C7 C6 116.49(15) . . ?
C8 C7 H7 121.8 . . ?
C6 C7 H7 121.8 . . ?
C7 C6 C5 122.47(14) . . ?
C7 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?

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
C6 C5 C4 C3 0.7(2) . . . . ?
C15 C5 C4 C3 -178.28(14) . . . . ?
C5 C4 C3 C8 0.2(2) . . . . ?
C5 C4 C3 C2 177.77(13) . . . . ?
C8 C3 C2 C9 -125.17(12) . . . . ?
C4 C3 C2 C9 57.1(2) . . . . ?
C8 C3 C2 C1 -2.03(14) . . . . ?
C4 C3 C2 C1 -179.79(14) . . . . ?
C3 C2 C9 C10 -152.60(13) . . . . ?
C1 C2 C9 C10 89.63(15) . . . . ?
C3 C2 C9 C14 29.08(19) . . . . ?
C1 C2 C9 C14 -88.69(17) . . . . ?
C14 C9 C10 C11 0.2(2) . . . . ?
C2 C9 C10 C11 -178.15(14) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C10 C9 C14 C13 -0.2(2) . . . . ?
C2 C9 C14 C13 178.12(15) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C9 C14 C13 C12 0.0(3) . . . . ?
C8 O2 C1 O1 178.63(14) . . . . ?
C8 O2 C1 C2 -2.01(15) . . . . ?
C3 C2 C1 O1 -178.24(16) . . . . ?
C9 C2 C1 O1 -50.5(2) . . . . ?
C3 C2 C1 O2 2.48(14) . . . . ?
C9 C2 C1 O2 130.20(12) . . . . ?
C4 C3 C8 C7 -1.1(2) . . . . ?
C2 C3 C8 C7 -179.21(13) . . . . ?
C4 C3 C8 O2 179.14(11) . . . . ?
C2 C3 C8 O2 1.01(15) . . . . ?
C1 O2 C8 C7 -179.14(13) . . . . ?
C1 O2 C8 C3 0.64(16) . . . . ?
C3 C8 C7 C6 1.0(2) . . . . ?
O2 C8 C7 C6 -179.29(13) . . . . ?
C8 C7 C6 C5 0.0(2) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C15 C5 C6 C7 178.15(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.035
