# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_mo_dd19317_0m
_database_code_depnum_ccdc_archive 'CCDC 1975819'
loop_
_audit_author_name
_audit_author_address
'Zhipeng Zhang'
;South China University of Technology
China
;
_audit_update_record             
;
2020-01-07 deposited with the CCDC.	2020-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H9 F O2'
_chemical_formula_weight         192.18

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'
F F 0.0171 0.0103 '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/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.2958(8)
_cell_length_b                   7.8128(7)
_cell_length_c                   14.5059(16)
_cell_angle_alpha                90
_cell_angle_beta                 98.757(3)
_cell_angle_gamma                90
_cell_volume                     929.22(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4137
_cell_measurement_theta_min      6.958
_cell_measurement_theta_max      54.630

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6198
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9686
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.479
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_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 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1716
_reflns_number_gt                1377
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0751P)²+0.1610P] 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         1716
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1458
_refine_ls_wR_factor_gt          0.1343
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
F1 F 0.52464(17) 0.61934(18) 0.74798(9) 0.1042(5) Uani 1 1 d . . . . .
O1 O 0.76025(18) 0.15895(15) 0.56253(9) 0.0800(5) Uani 1 1 d . . . . .
O2 O 0.78516(15) 0.60855(16) 0.42651(9) 0.0716(4) Uani 1 1 d . . . . .
C1 C 0.72190(19) 0.6055(2) 0.50826(13) 0.0598(4) Uani 1 1 d . . . . .
C2 C 0.6702(2) 0.7603(2) 0.54043(16) 0.0785(6) Uani 1 1 d . . . . .
H2 H 0.6802 0.8608 0.5074 0.094 Uiso 1 1 calc R U . . .
C3 C 0.6047(2) 0.7634(3) 0.62095(17) 0.0826(6) Uani 1 1 d . . . . .
H3 H 0.5694 0.8658 0.6437 0.099 Uiso 1 1 calc R U . . .
C4 C 0.5915(2) 0.6127(2) 0.66814(14) 0.0716(5) Uani 1 1 d . . . . .
C5 C 0.64078(19) 0.4594(2) 0.63846(12) 0.0611(4) Uani 1 1 d . . . . .
H5 H 0.6294 0.3599 0.6720 0.073 Uiso 1 1 calc R U . . .
C6 C 0.70902(17) 0.45491(18) 0.55628(11) 0.0514(4) Uani 1 1 d . . . . .
C7 C 0.76601(19) 0.29440(19) 0.52042(11) 0.0559(4) Uani 1 1 d . . . . .
C8 C 0.82832(19) 0.3070(2) 0.43283(11) 0.0612(4) Uani 1 1 d . . . . .
C9 C 0.83539(19) 0.4592(3) 0.39105(12) 0.0657(5) Uani 1 1 d . . . . .
C10 C 0.8964(3) 0.4937(4) 0.30132(14) 0.0972(8) Uani 1 1 d . . . . .
H10A H 0.8184 0.4528 0.2504 0.146 Uiso 1 1 calc R U . . .
H10B H 0.9985 0.4359 0.3012 0.146 Uiso 1 1 calc R U . . .
H10C H 0.9115 0.6146 0.2946 0.146 Uiso 1 1 calc R U . . .
C11 C 0.8818(3) 0.1454(3) 0.39116(16) 0.0879(6) Uani 1 1 d . . . . .
H11A H 0.9848 0.1097 0.4251 0.132 Uiso 1 1 calc R U . . .
H11B H 0.8930 0.1652 0.3271 0.132 Uiso 1 1 calc R U . . .
H11C H 0.8020 0.0576 0.3945 0.132 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
F1 C4 1.359(2) . ?
O1 C7 1.2265(19) . ?
O2 C9 1.366(2) . ?
O2 C1 1.368(2) . ?
C1 C6 1.380(2) . ?
C1 C2 1.388(3) . ?
C2 C3 1.361(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.356(2) . ?
C5 C6 1.396(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.463(2) . ?
C7 C8 1.446(2) . ?
C8 C9 1.340(3) . ?
C8 C11 1.496(3) . ?
C9 C10 1.491(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
C9 O2 C1 119.40(13) . . ?
O2 C1 C6 121.46(15) . . ?
O2 C1 C2 117.08(16) . . ?
C6 C1 C2 121.46(18) . . ?
C3 C2 C1 119.19(18) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.00(18) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 F1 119.09(18) . . ?
C5 C4 C3 123.18(19) . . ?
F1 C4 C3 117.73(17) . . ?
C4 C5 C6 118.33(17) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C5 118.83(15) . . ?
C1 C6 C7 119.82(15) . . ?
C5 C6 C7 121.35(14) . . ?
O1 C7 C8 122.85(15) . . ?
O1 C7 C6 121.55(14) . . ?
C8 C7 C6 115.60(14) . . ?
C9 C8 C7 120.25(17) . . ?
C9 C8 C11 122.01(17) . . ?
C7 C8 C11 117.74(17) . . ?
C8 C9 O2 123.44(15) . . ?
C8 C9 C10 126.8(2) . . ?
O2 C9 C10 109.74(18) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
C9 O2 C1 C6 0.6(2) . . . . ?
C9 O2 C1 C2 -178.96(15) . . . . ?
O2 C1 C2 C3 179.26(15) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C2 C3 C4 F1 -179.57(16) . . . . ?
F1 C4 C5 C6 179.93(14) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
O2 C1 C6 C5 -178.87(13) . . . . ?
C2 C1 C6 C5 0.7(2) . . . . ?
O2 C1 C6 C7 0.9(2) . . . . ?
C2 C1 C6 C7 -179.55(15) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C4 C5 C6 C7 179.53(14) . . . . ?
C1 C6 C7 O1 178.12(16) . . . . ?
C5 C6 C7 O1 -2.1(2) . . . . ?
C1 C6 C7 C8 -2.0(2) . . . . ?
C5 C6 C7 C8 177.73(13) . . . . ?
O1 C7 C8 C9 -178.36(16) . . . . ?
C6 C7 C8 C9 1.8(2) . . . . ?
O1 C7 C8 C11 2.3(3) . . . . ?
C6 C7 C8 C11 -177.56(14) . . . . ?
C7 C8 C9 O2 -0.4(3) . . . . ?
C11 C8 C9 O2 178.94(16) . . . . ?
C7 C8 C9 C10 179.83(16) . . . . ?
C11 C8 C9 C10 -0.9(3) . . . . ?
C1 O2 C9 C8 -0.9(2) . . . . ?
C1 O2 C9 C10 178.93(14) . . . . ?

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
C5 H5 F1 0.93 2.64 3.514(2) 157.0 2_646
C2 H2 O1 0.93 2.52 3.207(2) 131.1 1_565
C5 H5 F1 0.93 2.64 3.514(2) 157.0 2_646
C2 H2 O1 0.93 2.52 3.207(2) 131.1 1_565
C5 H5 F1 0.93 2.64 3.514(2) 157.0 2_646
C2 H2 O1 0.93 2.52 3.207(2) 131.1 1_565
C2 H2 O1 0.93 2.52 3.207(2) 131.1 1_565
C5 H5 F1 0.93 2.64 3.514(2) 157.0 2_646

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.028

_shelxl_version_number           2013-4

