# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_20221019s_0m
_database_code_depnum_ccdc_archive 'CCDC 2215372'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D2CC06068J 2023
loop_
_audit_author_name
_audit_author_address
'Wang L.'
;Zhejiang Normal University
China
;
_audit_update_record             
;
2022-10-26 deposited with the CCDC.	2023-01-18 downloaded from the CCDC.
;
_audit_creation_date             2022-10-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
lywang@zjnu.edu.cn
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H24 F N O2'
_chemical_formula_sum            'C19 H24 F N O2'
_chemical_formula_weight         317.39
_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 0.0181 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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2396(2)
_cell_length_b                   9.9099(4)
_cell_length_c                   14.5635(6)
_cell_angle_alpha                98.240(2)
_cell_angle_beta                 98.468(2)
_cell_angle_gamma                91.823(2)
_cell_volume                     880.22(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3546
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      68.028
_cell_measurement_theta_min      5.854
_shelx_estimated_absorpt_T_max   0.843
_shelx_estimated_absorpt_T_min   0.811
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1314
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10704
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.196
_diffrn_reflns_theta_min         5.854
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2453
_reflns_number_total             3199
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.057(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0682
_refine_ls_restrained_S_all      1.048
_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)+(0.0974P)²+0.2087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1828
_refine_ls_wR_factor_ref         0.2032
_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:
 C005(H005)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00C), C00G(H00F,H00G), C00K(H00M,H00N)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00D(H00D), C00E(H00E), C00I(H00K), C00J(H00L)
2.d Idealised Me refined as rotating group:
 C00H(H00H,H00I,H00J), C00L(H00O,H00P,H00Q), C00M(H00R,H00S,H00T), C00N(H00U,
 H00V,H00W)
;
_atom_sites_solution_hydrogens   geom
_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
F001 F 0.2560(3) 0.65240(14) 0.38811(10) 0.0726(5) Uani 1 1 d . . . . .
O002 O 0.2644(3) 0.50537(19) 0.54035(12) 0.0679(5) Uani 1 1 d . . . . .
O003 O -0.0028(3) 0.4850(2) 0.18837(13) 0.0703(6) Uani 1 1 d . . . . .
N004 N 0.3173(3) 0.6009(2) 0.19268(14) 0.0626(6) Uani 1 1 d . . . . .
C005 C 0.1662(3) 0.2710(2) 0.32146(15) 0.0519(6) Uani 1 1 d . . . . .
H005 H 0.009206 0.258193 0.300742 0.062 Uiso 1 1 calc R U . . .
C006 C 0.2111(3) 0.4159(2) 0.37403(15) 0.0515(6) Uani 1 1 d . . . . .
C007 C 0.2751(3) 0.2351(2) 0.23565(15) 0.0519(6) Uani 1 1 d . . . . .
C008 C 0.2193(4) 0.5272(2) 0.33505(16) 0.0543(6) Uani 1 1 d . . . . .
C009 C 0.2217(4) 0.4110(2) 0.47674(16) 0.0567(6) Uani 1 1 d . . . . .
C00A C 0.1706(4) 0.5361(2) 0.23182(16) 0.0546(6) Uani 1 1 d . . . . .
C00B C 0.4810(4) 0.2879(2) 0.23030(18) 0.0569(6) Uani 1 1 d . . . . .
H00B H 0.555775 0.347409 0.280912 0.068 Uiso 1 1 calc R U . . .
C00C C 0.2256(4) 0.1790(2) 0.39986(17) 0.0588(6) Uani 1 1 d . . . . .
C00D C 0.1686(4) 0.1448(3) 0.15953(18) 0.0626(6) Uani 1 1 d . . . . .
H00D H 0.030751 0.107932 0.161596 0.075 Uiso 1 1 calc R U . . .
C00E C 0.5765(4) 0.2535(3) 0.15092(19) 0.0661(7) Uani 1 1 d . . . . .
H00E H 0.713561 0.290891 0.148093 0.079 Uiso 1 1 calc R U . . .
C00F C 0.5386(4) 0.6418(3) 0.2384(2) 0.0693(7) Uani 1 1 d . . . . .
H00A H 0.639329 0.595431 0.201611 0.083 Uiso 1 1 calc R U . . .
H00C H 0.560628 0.612593 0.299747 0.083 Uiso 1 1 calc R U . . .
C00G C 0.1611(5) 0.2661(3) 0.48598(18) 0.0678(7) Uani 1 1 d . . . . .
H00F H 0.006455 0.254200 0.486724 0.081 Uiso 1 1 calc R U . . .
H00G H 0.238795 0.241270 0.543339 0.081 Uiso 1 1 calc R U . . .
C00H C 0.4674(4) 0.1575(3) 0.4180(2) 0.0693(7) Uani 1 1 d . . . . .
H00H H 0.509464 0.104773 0.363529 0.104 Uiso 1 1 calc R U . . .
H00I H 0.498744 0.109584 0.470814 0.104 Uiso 1 1 calc R U . . .
H00J H 0.546682 0.244405 0.431036 0.104 Uiso 1 1 calc R U . . .
C00I C 0.4689(5) 0.1637(3) 0.0758(2) 0.0722(7) Uani 1 1 d . . . . .
H00K H 0.533159 0.140309 0.022464 0.087 Uiso 1 1 calc R U . . .
C00J C 0.2663(5) 0.1091(3) 0.0805(2) 0.0724(7) Uani 1 1 d . . . . .
H00L H 0.194084 0.047868 0.030263 0.087 Uiso 1 1 calc R U . . .
C00K C 0.2637(5) 0.6090(4) 0.0914(2) 0.0840(9) Uani 1 1 d . . . . .
H00M H 0.396269 0.630359 0.067787 0.101 Uiso 1 1 calc R U . . .
H00N H 0.205902 0.520129 0.058787 0.101 Uiso 1 1 calc R U . . .
C00L C 0.0978(5) 0.0411(3) 0.3752(2) 0.0780(8) Uani 1 1 d . . . . .
H00O H -0.054828 0.055515 0.366508 0.117 Uiso 1 1 calc R U . . .
H00P H 0.132254 -0.011582 0.425367 0.117 Uiso 1 1 calc R U . . .
H00Q H 0.135659 -0.007249 0.318408 0.117 Uiso 1 1 calc R U . . .
C00M C 0.5893(7) 0.7937(4) 0.2502(3) 0.1092(13) Uani 1 1 d . . . . .
H00R H 0.567494 0.823537 0.189769 0.164 Uiso 1 1 calc R U . . .
H00S H 0.737519 0.813965 0.278961 0.164 Uiso 1 1 calc R U . . .
H00T H 0.495123 0.840159 0.289217 0.164 Uiso 1 1 calc R U . . .
C00N C 0.1068(7) 0.7109(5) 0.0694(3) 0.1181(14) Uani 1 1 d . . . . .
H00U H 0.077999 0.709248 0.002627 0.177 Uiso 1 1 calc R U . . .
H00V H 0.165178 0.799884 0.099068 0.177 Uiso 1 1 calc R U . . .
H00W H -0.025612 0.690255 0.091995 0.177 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
F001 C008 1.358(3) . ?
O002 C009 1.211(3) . ?
O003 C00A 1.225(3) . ?
N004 C00A 1.340(3) . ?
N004 C00F 1.460(3) . ?
N004 C00K 1.477(3) . ?
C005 H005 0.9800 . ?
C005 C006 1.524(3) . ?
C005 C007 1.513(3) . ?
C005 C00C 1.571(3) . ?
C006 C008 1.313(3) . ?
C006 C009 1.495(3) . ?
C007 C00B 1.389(3) . ?
C007 C00D 1.390(3) . ?
C008 C00A 1.505(3) . ?
C009 C00G 1.503(4) . ?
C00B H00B 0.9300 . ?
C00B C00E 1.382(3) . ?
C00C C00G 1.530(4) . ?
C00C C00H 1.520(4) . ?
C00C C00L 1.529(3) . ?
C00D H00D 0.9300 . ?
C00D C00J 1.388(4) . ?
C00E H00E 0.9300 . ?
C00E C00I 1.380(4) . ?
C00F H00A 0.9700 . ?
C00F H00C 0.9700 . ?
C00F C00M 1.508(4) . ?
C00G H00F 0.9700 . ?
C00G H00G 0.9700 . ?
C00H H00H 0.9600 . ?
C00H H00I 0.9600 . ?
C00H H00J 0.9600 . ?
C00I H00K 0.9300 . ?
C00I C00J 1.374(4) . ?
C00J H00L 0.9300 . ?
C00K H00M 0.9700 . ?
C00K H00N 0.9700 . ?
C00K C00N 1.464(5) . ?
C00L H00O 0.9600 . ?
C00L H00P 0.9600 . ?
C00L H00Q 0.9600 . ?
C00M H00R 0.9600 . ?
C00M H00S 0.9600 . ?
C00M H00T 0.9600 . ?
C00N H00U 0.9600 . ?
C00N H00V 0.9600 . ?
C00N H00W 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
C00A N004 C00F 124.3(2) . . ?
C00A N004 C00K 117.2(2) . . ?
C00F N004 C00K 117.6(2) . . ?
C006 C005 H005 107.3 . . ?
C006 C005 C00C 103.63(17) . . ?
C007 C005 H005 107.3 . . ?
C007 C005 C006 116.64(18) . . ?
C007 C005 C00C 114.29(18) . . ?
C00C C005 H005 107.3 . . ?
C008 C006 C005 125.6(2) . . ?
C008 C006 C009 125.8(2) . . ?
C009 C006 C005 108.37(19) . . ?
C00B C007 C005 122.25(19) . . ?
C00B C007 C00D 118.2(2) . . ?
C00D C007 C005 119.5(2) . . ?
F001 C008 C00A 112.04(19) . . ?
C006 C008 F001 121.2(2) . . ?
C006 C008 C00A 126.5(2) . . ?
O002 C009 C006 127.1(2) . . ?
O002 C009 C00G 126.3(2) . . ?
C006 C009 C00G 106.55(19) . . ?
O003 C00A N004 123.5(2) . . ?
O003 C00A C008 117.9(2) . . ?
N004 C00A C008 118.51(19) . . ?
C007 C00B H00B 119.5 . . ?
C00E C00B C007 121.0(2) . . ?
C00E C00B H00B 119.5 . . ?
C00G C00C C005 101.88(19) . . ?
C00H C00C C005 112.2(2) . . ?
C00H C00C C00G 109.1(2) . . ?
C00H C00C C00L 110.0(2) . . ?
C00L C00C C005 111.1(2) . . ?
C00L C00C C00G 112.3(2) . . ?
C007 C00D H00D 119.7 . . ?
C00J C00D C007 120.5(2) . . ?
C00J C00D H00D 119.7 . . ?
C00B C00E H00E 119.9 . . ?
C00I C00E C00B 120.1(2) . . ?
C00I C00E H00E 119.9 . . ?
N004 C00F H00A 108.9 . . ?
N004 C00F H00C 108.9 . . ?
N004 C00F C00M 113.3(3) . . ?
H00A C00F H00C 107.7 . . ?
C00M C00F H00A 108.9 . . ?
C00M C00F H00C 108.9 . . ?
C009 C00G C00C 105.3(2) . . ?
C009 C00G H00F 110.7 . . ?
C009 C00G H00G 110.7 . . ?
C00C C00G H00F 110.7 . . ?
C00C C00G H00G 110.7 . . ?
H00F C00G H00G 108.8 . . ?
C00C C00H H00H 109.5 . . ?
C00C C00H H00I 109.5 . . ?
C00C C00H H00J 109.5 . . ?
H00H C00H H00I 109.5 . . ?
H00H C00H H00J 109.5 . . ?
H00I C00H H00J 109.5 . . ?
C00E C00I H00K 120.2 . . ?
C00J C00I C00E 119.6(2) . . ?
C00J C00I H00K 120.2 . . ?
C00D C00J H00L 119.8 . . ?
C00I C00J C00D 120.5(2) . . ?
C00I C00J H00L 119.8 . . ?
N004 C00K H00M 108.7 . . ?
N004 C00K H00N 108.7 . . ?
H00M C00K H00N 107.6 . . ?
C00N C00K N004 114.1(3) . . ?
C00N C00K H00M 108.7 . . ?
C00N C00K H00N 108.7 . . ?
C00C C00L H00O 109.5 . . ?
C00C C00L H00P 109.5 . . ?
C00C C00L H00Q 109.5 . . ?
H00O C00L H00P 109.5 . . ?
H00O C00L H00Q 109.5 . . ?
H00P C00L H00Q 109.5 . . ?
C00F C00M H00R 109.5 . . ?
C00F C00M H00S 109.5 . . ?
C00F C00M H00T 109.5 . . ?
H00R C00M H00S 109.5 . . ?
H00R C00M H00T 109.5 . . ?
H00S C00M H00T 109.5 . . ?
C00K C00N H00U 109.5 . . ?
C00K C00N H00V 109.5 . . ?
C00K C00N H00W 109.5 . . ?
H00U C00N H00V 109.5 . . ?
H00U C00N H00W 109.5 . . ?
H00V C00N H00W 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
F001 C008 C00A O003 -121.6(2) . . . . ?
F001 C008 C00A N004 57.5(3) . . . . ?
O002 C009 C00G C00C -154.5(2) . . . . ?
C005 C006 C008 F001 178.60(19) . . . . ?
C005 C006 C008 C00A 4.7(4) . . . . ?
C005 C006 C009 O002 176.3(2) . . . . ?
C005 C006 C009 C00G -5.6(2) . . . . ?
C005 C007 C00B C00E -179.9(2) . . . . ?
C005 C007 C00D C00J -179.3(2) . . . . ?
C005 C00C C00G C009 -37.6(2) . . . . ?
C006 C005 C007 C00B 34.9(3) . . . . ?
C006 C005 C007 C00D -146.0(2) . . . . ?
C006 C005 C00C C00G 33.4(2) . . . . ?
C006 C005 C00C C00H -83.2(2) . . . . ?
C006 C005 C00C C00L 153.2(2) . . . . ?
C006 C008 C00A O003 52.7(3) . . . . ?
C006 C008 C00A N004 -128.2(3) . . . . ?
C006 C009 C00G C00C 27.5(3) . . . . ?
C007 C005 C006 C008 41.5(3) . . . . ?
C007 C005 C006 C009 -144.14(19) . . . . ?
C007 C005 C00C C00G 161.39(19) . . . . ?
C007 C005 C00C C00H 44.8(3) . . . . ?
C007 C005 C00C C00L -78.8(3) . . . . ?
C007 C00B C00E C00I -1.0(4) . . . . ?
C007 C00D C00J C00I -0.7(4) . . . . ?
C008 C006 C009 O002 -9.3(4) . . . . ?
C008 C006 C009 C00G 168.7(2) . . . . ?
C009 C006 C008 F001 5.2(4) . . . . ?
C009 C006 C008 C00A -168.7(2) . . . . ?
C00A N004 C00F C00M -120.1(3) . . . . ?
C00A N004 C00K C00N 76.7(4) . . . . ?
C00B C007 C00D C00J -0.2(4) . . . . ?
C00B C00E C00I C00J 0.1(4) . . . . ?
C00C C005 C006 C008 168.0(2) . . . . ?
C00C C005 C006 C009 -17.6(2) . . . . ?
C00C C005 C007 C00B -86.1(3) . . . . ?
C00C C005 C007 C00D 92.9(3) . . . . ?
C00D C007 C00B C00E 1.0(4) . . . . ?
C00E C00I C00J C00D 0.7(5) . . . . ?
C00F N004 C00A O003 -169.1(2) . . . . ?
C00F N004 C00A C008 11.9(4) . . . . ?
C00F N004 C00K C00N -113.9(3) . . . . ?
C00H C00C C00G C009 81.2(2) . . . . ?
C00K N004 C00A O003 -0.4(4) . . . . ?
C00K N004 C00A C008 -179.4(2) . . . . ?
C00K N004 C00F C00M 71.3(3) . . . . ?
C00L C00C C00G C009 -156.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2022042705_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2215733'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D2CC06068J 2023
loop_
_audit_author_name
_audit_author_address
'Wang. L.'
;Zhejiang Normal University
China
;
_audit_update_record             
;
2022-10-27 deposited with the CCDC.	2023-01-18 downloaded from the CCDC.
;
_audit_creation_date             2022-04-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H19 F O5'
_chemical_formula_sum            'C18 H19 F O5'
_chemical_formula_weight         334.33
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0823(8)
_cell_length_b                   8.7728(10)
_cell_length_c                   13.8942(15)
_cell_angle_alpha                92.044(4)
_cell_angle_beta                 102.990(4)
_cell_angle_gamma                94.510(4)
_cell_volume                     837.31(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2605
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.855
_cell_measurement_theta_min      2.707
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0941 before and 0.0648 after correction.
The Ratio of minimum to maximum transmission is 0.8716.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_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       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16684
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.469
_diffrn_reflns_theta_min         2.332
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1889
_reflns_number_total             3827
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3827
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1586
_refine_ls_R_factor_gt           0.0758
_refine_ls_restrained_S_all      1.032
_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)+(0.0720P)²+0.3730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1666
_refine_ls_wR_factor_ref         0.2113
_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. Restrained distances
 C1-C2
 1.5 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C2(H2A,H2B)
3.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C13(H13), C14(H14)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C9(H9A,H9B,H9C), C1(H1A,H1B,H1C)
;
_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
O5 O 0.2890(4) 0.9162(2) 0.28102(19) 0.0814(7) Uani 1 1 d . . . . .
O4 O 0.0216(3) 0.7410(3) 0.2685(2) 0.0880(8) Uani 1 1 d . . . . .
F1 F 0.8037(3) 0.1332(3) 0.34096(19) 0.1246(9) Uani 1 1 d . . . . .
O3 O 0.8244(4) 0.1888(3) 0.1543(2) 0.1090(10) Uani 1 1 d . . . . .
C11 C 0.3615(4) 0.2956(3) 0.1915(2) 0.0530(7) Uani 1 1 d . . . . .
H11 H 0.2638 0.2374 0.2188 0.064 Uiso 1 1 calc R . . . .
C12 C 0.3566(4) 0.4643(3) 0.2167(2) 0.0540(7) Uani 1 1 d . . . . .
C5 C 0.5576(4) 0.2368(3) 0.2311(2) 0.0616(8) Uani 1 1 d . . . . .
O1 O 0.3894(5) 0.2525(3) 0.40094(19) 0.1067(10) Uani 1 1 d . . . . .
C18 C 0.1818(4) 0.5149(3) 0.2313(2) 0.0611(8) Uani 1 1 d . . . . .
H18 H 0.0728 0.4464 0.2272 0.073 Uiso 1 1 calc R . . . .
C13 C 0.5150(4) 0.5702(3) 0.2242(2) 0.0642(8) Uani 1 1 d . . . . .
H13 H 0.6316 0.5364 0.2155 0.077 Uiso 1 1 calc R . . . .
C17 C 0.1765(4) 0.6673(3) 0.2518(2) 0.0611(8) Uani 1 1 d . . . . .
C15 C 0.3349(5) 0.7705(3) 0.2583(2) 0.0621(8) Uani 1 1 d . . . . .
C8 C 0.3240(4) 0.2511(4) 0.0777(2) 0.0624(8) Uani 1 1 d . . . . .
C14 C 0.5059(5) 0.7269(4) 0.2445(2) 0.0686(9) Uani 1 1 d . . . . .
H14 H 0.6128 0.7975 0.2483 0.082 Uiso 1 1 calc R . . . .
C6 C 0.6612(5) 0.2273(4) 0.1486(3) 0.0741(9) Uani 1 1 d . . . . .
C4 C 0.6300(5) 0.1939(4) 0.3217(3) 0.0789(10) Uani 1 1 d . . . . .
C7 C 0.5271(5) 0.2759(4) 0.0577(3) 0.0759(10) Uani 1 1 d . . . . .
H7A H 0.5363 0.2142 -0.0001 0.091 Uiso 1 1 calc R . . . .
H7B H 0.5582 0.3827 0.0470 0.091 Uiso 1 1 calc R . . . .
C10 C 0.1774(5) 0.3449(5) 0.0139(3) 0.0869(11) Uani 1 1 d . . . . .
H10A H 0.0524 0.3242 0.0290 0.130 Uiso 1 1 calc GR . . . .
H10B H 0.1681 0.3178 -0.0547 0.130 Uiso 1 1 calc GR . . . .
H10C H 0.2191 0.4519 0.0271 0.130 Uiso 1 1 calc GR . . . .
C9 C 0.2549(5) 0.0804(4) 0.0609(3) 0.0824(10) Uani 1 1 d . . . . .
H9A H 0.3496 0.0220 0.1003 0.124 Uiso 1 1 calc GR . . . .
H9B H 0.2389 0.0500 -0.0078 0.124 Uiso 1 1 calc GR . . . .
H9C H 0.1328 0.0622 0.0795 0.124 Uiso 1 1 calc GR . . . .
C16 C 0.0968(6) 0.8971(4) 0.2952(4) 0.0859(11) Uani 1 1 d . . . . .
O2 O 0.6520(6) 0.1606(5) 0.4893(3) 0.1710(17) Uani 1 1 d . . . . .
C3 C 0.5560(7) 0.2000(5) 0.4121(3) 0.0944(12) Uani 1 1 d . . . . .
C2 C 0.3044(11) 0.2623(7) 0.4885(4) 0.168(3) Uani 1 1 d D . . . .
H2A H 0.2232 0.1685 0.4902 0.201 Uiso 1 1 calc R . . . .
H2B H 0.4087 0.2705 0.5477 0.201 Uiso 1 1 calc R . . . .
C1 C 0.1980(11) 0.3812(8) 0.4895(5) 0.180(3) Uani 1 1 d D . . . .
H1A H 0.2799 0.4749 0.4937 0.269 Uiso 1 1 calc GR . . . .
H1B H 0.1400 0.3780 0.5456 0.269 Uiso 1 1 calc GR . . . .
H1C H 0.0976 0.3763 0.4299 0.269 Uiso 1 1 calc GR . . . .
H16A H 0.016(6) 0.965(4) 0.250(3) 0.110(13) Uiso 1 1 d . . . . .
H16B H 0.111(6) 0.926(5) 0.372(4) 0.126(15) Uiso 1 1 d . . . . .


_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
O5 C15 1.386(3) . ?
O5 C16 1.417(5) . ?
O4 C17 1.376(3) . ?
O4 C16 1.434(4) . ?
F1 C4 1.355(4) . ?
O3 C6 1.216(4) . ?
C11 H11 0.9800 . ?
C11 C12 1.513(4) . ?
C11 C5 1.512(4) . ?
C11 C8 1.574(4) . ?
C12 C18 1.401(4) . ?
C12 C13 1.382(4) . ?
C5 C6 1.497(5) . ?
C5 C4 1.327(5) . ?
O1 C3 1.280(5) . ?
O1 C2 1.476(5) . ?
C18 H18 0.9300 . ?
C18 C17 1.362(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.403(4) . ?
C17 C15 1.370(4) . ?
C15 C14 1.349(4) . ?
C8 C7 1.525(4) . ?
C8 C10 1.522(4) . ?
C8 C9 1.531(4) . ?
C14 H14 0.9300 . ?
C6 C7 1.498(5) . ?
C4 C3 1.466(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C16 H16A 0.99(4) . ?
C16 H16B 1.07(5) . ?
O2 C3 1.211(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.336(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
C15 O5 C16 105.6(3) . . ?
C17 O4 C16 105.4(3) . . ?
C12 C11 H11 108.8 . . ?
C12 C11 C8 114.7(2) . . ?
C5 C11 H11 108.8 . . ?
C5 C11 C12 113.4(2) . . ?
C5 C11 C8 102.1(2) . . ?
C8 C11 H11 108.8 . . ?
C18 C12 C11 118.1(3) . . ?
C13 C12 C11 123.0(2) . . ?
C13 C12 C18 118.9(3) . . ?
C6 C5 C11 108.5(3) . . ?
C4 C5 C11 128.0(3) . . ?
C4 C5 C6 123.5(3) . . ?
C3 O1 C2 117.5(4) . . ?
C12 C18 H18 121.0 . . ?
C17 C18 C12 118.0(3) . . ?
C17 C18 H18 121.0 . . ?
C12 C13 H13 118.9 . . ?
C12 C13 C14 122.2(3) . . ?
C14 C13 H13 118.9 . . ?
C18 C17 O4 127.6(3) . . ?
C18 C17 C15 122.2(3) . . ?
C15 C17 O4 110.1(3) . . ?
C17 C15 O5 109.8(3) . . ?
C14 C15 O5 128.4(3) . . ?
C14 C15 C17 121.8(3) . . ?
C7 C8 C11 102.6(2) . . ?
C7 C8 C9 108.9(3) . . ?
C10 C8 C11 113.5(2) . . ?
C10 C8 C7 113.0(3) . . ?
C10 C8 C9 110.1(3) . . ?
C9 C8 C11 108.5(2) . . ?
C13 C14 H14 121.5 . . ?
C15 C14 C13 116.9(3) . . ?
C15 C14 H14 121.5 . . ?
O3 C6 C5 126.5(4) . . ?
O3 C6 C7 126.2(3) . . ?
C5 C6 C7 107.2(3) . . ?
F1 C4 C3 109.3(3) . . ?
C5 C4 F1 119.1(4) . . ?
C5 C4 C3 131.6(3) . . ?
C8 C7 H7A 110.8 . . ?
C8 C7 H7B 110.8 . . ?
C6 C7 C8 105.0(3) . . ?
C6 C7 H7A 110.8 . . ?
C6 C7 H7B 110.8 . . ?
H7A C7 H7B 108.8 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
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 . . ?
O5 C16 O4 108.5(3) . . ?
O5 C16 H16A 108(2) . . ?
O5 C16 H16B 105(2) . . ?
O4 C16 H16A 109(2) . . ?
O4 C16 H16B 112(2) . . ?
H16A C16 H16B 114(3) . . ?
O1 C3 C4 114.1(3) . . ?
O2 C3 O1 125.3(5) . . ?
O2 C3 C4 120.6(4) . . ?
O1 C2 H2A 108.9 . . ?
O1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C1 C2 O1 113.2(5) . . ?
C1 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
O5 C15 C14 C13 178.6(3) . . . . ?
O4 C17 C15 O5 0.9(4) . . . . ?
O4 C17 C15 C14 -179.8(3) . . . . ?
F1 C4 C3 O1 -178.4(3) . . . . ?
F1 C4 C3 O2 3.2(6) . . . . ?
O3 C6 C7 C8 158.4(3) . . . . ?
C11 C12 C18 C17 -178.6(3) . . . . ?
C11 C12 C13 C14 177.9(3) . . . . ?
C11 C5 C6 O3 177.8(3) . . . . ?
C11 C5 C6 C7 -1.6(3) . . . . ?
C11 C5 C4 F1 175.0(3) . . . . ?
C11 C5 C4 C3 -5.4(6) . . . . ?
C11 C8 C7 C6 36.3(3) . . . . ?
C12 C11 C5 C6 -100.3(3) . . . . ?
C12 C11 C5 C4 81.9(4) . . . . ?
C12 C11 C8 C7 86.7(3) . . . . ?
C12 C11 C8 C10 -35.5(4) . . . . ?
C12 C11 C8 C9 -158.1(2) . . . . ?
C12 C18 C17 O4 179.9(3) . . . . ?
C12 C18 C17 C15 0.0(5) . . . . ?
C12 C13 C14 C15 1.1(5) . . . . ?
C5 C11 C12 C18 -147.9(3) . . . . ?
C5 C11 C12 C13 33.2(4) . . . . ?
C5 C11 C8 C7 -36.4(3) . . . . ?
C5 C11 C8 C10 -158.6(3) . . . . ?
C5 C11 C8 C9 78.7(3) . . . . ?
C5 C6 C7 C8 -22.1(3) . . . . ?
C5 C4 C3 O1 2.0(6) . . . . ?
C5 C4 C3 O2 -176.4(4) . . . . ?
C18 C12 C13 C14 -1.0(5) . . . . ?
C18 C17 C15 O5 -179.2(3) . . . . ?
C18 C17 C15 C14 0.1(5) . . . . ?
C13 C12 C18 C17 0.4(4) . . . . ?
C17 O4 C16 O5 7.6(4) . . . . ?
C17 C15 C14 C13 -0.6(5) . . . . ?
C15 O5 C16 O4 -7.1(4) . . . . ?
C8 C11 C12 C18 95.3(3) . . . . ?
C8 C11 C12 C13 -83.7(3) . . . . ?
C8 C11 C5 C6 23.7(3) . . . . ?
C8 C11 C5 C4 -154.1(3) . . . . ?
C6 C5 C4 F1 -2.4(5) . . . . ?
C6 C5 C4 C3 177.2(4) . . . . ?
C4 C5 C6 O3 -4.3(5) . . . . ?
C4 C5 C6 C7 176.3(3) . . . . ?
C10 C8 C7 C6 158.8(3) . . . . ?
C9 C8 C7 C6 -78.5(3) . . . . ?
C16 O5 C15 C17 3.9(4) . . . . ?
C16 O5 C15 C14 -175.4(4) . . . . ?
C16 O4 C17 C18 174.9(3) . . . . ?
C16 O4 C17 C15 -5.2(4) . . . . ?
C3 O1 C2 C1 146.7(6) . . . . ?
C2 O1 C3 C4 180.0(4) . . . . ?
C2 O1 C3 O2 -1.7(7) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
