# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_pher1_0m
_audit_block_doi                 10.5517/ccdc.csd.cc24bdxt
_database_code_depnum_ccdc_archive 'CCDC 1976216'
loop_
_audit_author_name
_audit_author_address
'Jianping yang'
;stockholm university
Sweden
;
_audit_update_record             
;
2020-01-08 deposited with the CCDC.	2020-08-25 downloaded from the CCDC.
;
_audit_creation_date             2019-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H9 F3 O'
_chemical_formula_sum            'C9 H9 F3 O'
_chemical_formula_weight         190.16
_chemical_absolute_configuration ad
_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'
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'

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

_cell_length_a                   4.71210(10)
_cell_length_b                   9.8742(2)
_cell_length_c                   17.9278(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     834.15(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9955
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.952
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_unetI/netI     0.0073
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16665
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.329
_diffrn_reflns_theta_min         2.272
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'sealed X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2027
_reflns_number_total             2057
_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       'COSMO (Bruker, V1.61, 2009)'
_computing_data_collection       'COSMO (Bruker, V1.61, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 823 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2057
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0244
_refine_ls_restrained_S_all      1.068
_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)+(0.0388P)²+0.1785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0674
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.5847(2) 0.69904(11) 0.02009(6) 0.0216(2) Uani 1 1 d . . . . .
F2 F -0.06514(19) 0.05946(9) 0.25021(5) 0.0237(2) Uani 1 1 d . . . . .
F1 F 0.22049(18) 0.47835(9) 0.06716(5) 0.0223(2) Uani 1 1 d . . . . .
F3 F 0.1255(2) -0.12849(9) 0.15434(5) 0.0266(2) Uani 1 1 d . . . . .
C9 C 0.2484(3) 0.22363(13) 0.20094(7) 0.0159(3) Uani 1 1 d . . . . .
H9 H 0.181058 0.288680 0.235751 0.019 Uiso 1 1 calc R . . . .
C8 C 0.1390(3) 0.09408(14) 0.20071(7) 0.0170(3) Uani 1 1 d . . . . .
C5 C 0.5536(3) 0.16047(13) 0.09926(7) 0.0174(3) Uani 1 1 d . . . . .
H5 H 0.695159 0.183779 0.063776 0.021 Uiso 1 1 calc R . . . .
C6 C 0.4447(3) 0.02933(14) 0.10004(7) 0.0191(3) Uani 1 1 d . . . . .
H6 H 0.512520 -0.036986 0.066045 0.023 Uiso 1 1 calc R . . . .
C4 C 0.4586(3) 0.25831(13) 0.14964(7) 0.0149(2) Uani 1 1 d . . . . .
C2 C 0.5163(3) 0.48086(13) 0.08047(7) 0.0153(2) Uani 1 1 d . . . . .
H2 H 0.617833 0.439771 0.037036 0.018 Uiso 1 1 calc R . . . .
C3 C 0.5800(3) 0.39975(13) 0.15017(7) 0.0156(2) Uani 1 1 d . . . . .
H3A H 0.788374 0.393713 0.156353 0.019 Uiso 1 1 calc R . . . .
H3B H 0.503322 0.448960 0.193857 0.019 Uiso 1 1 calc R . . . .
C7 C 0.2364(3) -0.00223(14) 0.15114(7) 0.0180(3) Uani 1 1 d . . . . .
C1 C 0.6038(3) 0.62739(13) 0.08861(7) 0.0176(3) Uani 1 1 d . . . . .
H1A H 0.480358 0.671741 0.126038 0.021 Uiso 1 1 calc R . . . .
H1B H 0.801502 0.631542 0.107126 0.021 Uiso 1 1 calc R . . . .
H1 H 0.423(5) 0.718(3) 0.0110(13) 0.037(6) Uiso 1 1 d . . . A 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0170(5) 0.0215(5) 0.0262(5) 0.0116(4) 0.0010(4) 0.0008(4)
F2 0.0226(4) 0.0242(4) 0.0243(4) 0.0063(3) 0.0078(3) -0.0009(3)
F1 0.0158(4) 0.0239(4) 0.0271(4) 0.0059(3) -0.0064(3) -0.0016(3)
F3 0.0354(5) 0.0145(4) 0.0297(4) 0.0013(3) 0.0046(4) -0.0072(4)
C9 0.0170(6) 0.0159(6) 0.0149(5) 0.0007(4) 0.0001(5) 0.0033(5)
C8 0.0159(6) 0.0190(6) 0.0160(6) 0.0049(5) 0.0013(5) 0.0012(5)
C5 0.0183(6) 0.0178(6) 0.0162(6) 0.0013(4) 0.0023(5) 0.0003(5)
C6 0.0235(7) 0.0163(6) 0.0176(6) -0.0018(5) 0.0012(5) 0.0019(5)
C4 0.0157(5) 0.0140(5) 0.0150(5) 0.0015(5) -0.0026(5) 0.0010(4)
C2 0.0137(6) 0.0155(6) 0.0167(5) 0.0020(5) 0.0000(4) 0.0003(4)
C3 0.0164(6) 0.0143(5) 0.0161(5) 0.0018(4) -0.0020(5) -0.0003(4)
C7 0.0219(6) 0.0131(6) 0.0191(6) 0.0025(5) -0.0021(5) -0.0020(5)
C1 0.0188(6) 0.0144(6) 0.0197(6) 0.0041(5) -0.0010(5) 0.0007(5)

_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 1.4205(16) . ?
F2 C8 1.3524(15) . ?
F1 C2 1.4143(15) . ?
F3 C7 1.3530(15) . ?
C9 C8 1.3791(18) . ?
C9 C4 1.3945(18) . ?
C8 C7 1.3802(19) . ?
C5 C6 1.3930(19) . ?
C5 C4 1.3962(18) . ?
C6 C7 1.3782(19) . ?
C4 C3 1.5092(17) . ?
C2 C3 1.5142(17) . ?
C2 C1 1.5115(18) . ?

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
C8 C9 C4 119.42(12) . . ?
F2 C8 C9 119.88(12) . . ?
F2 C8 C7 119.00(12) . . ?
C9 C8 C7 121.11(12) . . ?
C6 C5 C4 121.23(12) . . ?
C7 C6 C5 118.64(12) . . ?
C9 C4 C5 118.99(12) . . ?
C9 C4 C3 119.49(11) . . ?
C5 C4 C3 121.52(11) . . ?
F1 C2 C3 108.99(10) . . ?
F1 C2 C1 107.57(11) . . ?
C1 C2 C3 111.87(11) . . ?
C4 C3 C2 114.15(10) . . ?
F3 C7 C8 118.63(12) . . ?
F3 C7 C6 120.76(12) . . ?
C6 C7 C8 120.60(12) . . ?
O1 C1 C2 112.09(11) . . ?

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
C1 H1A F3 0.99 2.64 3.5039(17) 146.5 1_565
C1 H1B F1 0.99 2.59 3.2801(17) 126.9 1_655
O1 H1 O1 0.80(3) 1.88(3) 2.6613(9) 166(3) 3_465

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
F2 C8 C7 F3 -0.57(19) . . . . ?
F2 C8 C7 C6 -179.85(12) . . . . ?
F1 C2 C3 C4 52.61(15) . . . . ?
F1 C2 C1 O1 -69.25(14) . . . . ?
C9 C8 C7 F3 178.72(12) . . . . ?
C9 C8 C7 C6 -0.6(2) . . . . ?
C9 C4 C3 C2 -114.70(13) . . . . ?
C8 C9 C4 C5 -0.11(19) . . . . ?
C8 C9 C4 C3 -179.58(11) . . . . ?
C5 C6 C7 F3 -179.56(12) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C5 C4 C3 C2 65.85(16) . . . . ?
C6 C5 C4 C9 -0.7(2) . . . . ?
C6 C5 C4 C3 178.71(12) . . . . ?
C4 C9 C8 F2 -179.95(12) . . . . ?
C4 C9 C8 C7 0.8(2) . . . . ?
C4 C5 C6 C7 0.9(2) . . . . ?
C3 C2 C1 O1 171.09(11) . . . . ?
C1 C2 C3 C4 171.44(11) . . . . ?

_shelx_res_file                  
;
TITL Pher1_0m in P212121 #19
    pher1_0m.res
    created by SHELXL-2016/6 at 13:45:36 on 10-May-2019
CELL 0.71073 4.7121 9.8742 17.9278 90 90 90
ZERR 4 0.0001 0.0002 0.0003 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,-Z
SYMM -X,0.5+Y,0.5-Z
SFAC C H F O
UNIT 36 36 12 4
EQIV $1 +X,1+Y,+Z
EQIV $2 1+X,+Y,+Z
EQIV $3 -0.5+X,1.5-Y,-Z

L.S. 12
PLAN  10
SIZE 0.14 0.21 0.35
TEMP -173.14
HTAB C1 F3_$1
HTAB C1 F1_$2
HTAB O1 O1_$3
HTAB 2.00000
BOND
CONF
fmap 2
acta
MERG 2
REM <olex2.extras>
REM <HklSrc "%.\\Pher1_0m.hkl">
REM </olex2.extras>

WGHT    0.038800    0.178500
FVAR       0.28978
O1    4    0.584730    0.699043    0.020088    11.00000    0.01703    0.02152 =
         0.02620    0.01163    0.00102    0.00079
F2    3   -0.065139    0.059465    0.250205    11.00000    0.02263    0.02424 =
         0.02426    0.00632    0.00785   -0.00088
F1    3    0.220487    0.478352    0.067158    11.00000    0.01578    0.02393 =
         0.02712    0.00592   -0.00635   -0.00155
F3    3    0.125518   -0.128486    0.154339    11.00000    0.03545    0.01448 =
         0.02974    0.00127    0.00457   -0.00715
C9    1    0.248353    0.223630    0.200945    11.00000    0.01704    0.01595 =
         0.01485    0.00068    0.00007    0.00327
AFIX  43
H9    2    0.181058    0.288680    0.235751    11.00000   -1.20000
AFIX   0
C8    1    0.138967    0.094080    0.200714    11.00000    0.01588    0.01898 =
         0.01605    0.00492    0.00127    0.00119
C5    1    0.553595    0.160474    0.099255    11.00000    0.01826    0.01776 =
         0.01618    0.00130    0.00227    0.00030
AFIX  43
H5    2    0.695159    0.183779    0.063776    11.00000   -1.20000
AFIX   0
C6    1    0.444657    0.029333    0.100040    11.00000    0.02350    0.01626 =
         0.01761   -0.00184    0.00116    0.00189
AFIX  43
H6    2    0.512520   -0.036986    0.066045    11.00000   -1.20000
AFIX   0
C4    1    0.458602    0.258305    0.149641    11.00000    0.01566    0.01400 =
         0.01501    0.00151   -0.00257    0.00101
C2    1    0.516278    0.480863    0.080471    11.00000    0.01369    0.01545 =
         0.01672    0.00200   -0.00005    0.00034
AFIX  13
H2    2    0.617833    0.439771    0.037036    11.00000   -1.20000
AFIX   0
C3    1    0.579982    0.399748    0.150168    11.00000    0.01643    0.01430 =
         0.01614    0.00180   -0.00202   -0.00030
AFIX  23
H3A   2    0.788374    0.393713    0.156353    11.00000   -1.20000
H3B   2    0.503322    0.448960    0.193857    11.00000   -1.20000
AFIX   0
C7    1    0.236410   -0.002230    0.151143    11.00000    0.02192    0.01307 =
         0.01912    0.00250   -0.00208   -0.00201
C1    1    0.603756    0.627388    0.088612    11.00000    0.01877    0.01442 =
         0.01967    0.00414   -0.00096    0.00073
AFIX  23
H1A   2    0.480358    0.671741    0.126038    11.00000   -1.20000
H1B   2    0.801502    0.631542    0.107126    11.00000   -1.20000
AFIX   0
PART 2
H1    2    0.423273    0.717872    0.011009    11.00000    0.03707
HKLF 4




REM  Pher1_0m in P212121 #19
REM R1 =  0.0244 for    2027 Fo > 4sig(Fo)  and  0.0247 for all    2057 data
REM    122 parameters refined using      0 restraints

END

WGHT      0.0388      0.1785

REM Instructions for potential hydrogen bonds
EQIV $4 -x, y+1/2, -z+1/2
HTAB C9 F3_$4
HTAB C3 F2_$4
HTAB C1 F3_$1
HTAB C1 F1_$2
HTAB O1 O1_$3

REM Highest difference peak  0.252,  deepest hole -0.188,  1-sigma level  0.039
Q1    1   0.5622  0.5573  0.0832  11.00000  0.05    0.25
Q2    1   0.5339  0.4448  0.1161  11.00000  0.05    0.25
Q3    1   0.1978  0.0414  0.1824  11.00000  0.05    0.23
Q4    1   0.3563  0.2377  0.1795  11.00000  0.05    0.22
Q5    1   0.2024  0.1543  0.1996  11.00000  0.05    0.22
Q6    1   0.1345  0.0560  0.1642  11.00000  0.05    0.21
Q7    1   0.4747  0.0993  0.0997  11.00000  0.05    0.20
Q8    1   0.5103  0.3316  0.1469  11.00000  0.05    0.20
Q9    1   0.3119  0.2531  0.1649  11.00000  0.05    0.19
Q10   1   0.4970  0.2128  0.1193  11.00000  0.05    0.19
;
_shelx_res_checksum              57056
_olex2_submission_special_instructions 'No special instructions were received'
