# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_zn-240130-1r-296k_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2kfxvs
_database_code_depnum_ccdc_archive 'CCDC 2366876'
loop_
_audit_author_name
_audit_author_address
MaoWeiXin
;NanChang University
China
;
_audit_update_record             
;
2024-07-01 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;
_audit_creation_date             2024-07-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H4 F O2, C9 H14 N O'
_chemical_formula_sum            'C16 H18 F N O3'
_chemical_formula_weight         291.31
_chemical_absolute_configuration syn
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.2717(9)
_cell_length_b                   6.1735(9)
_cell_length_c                   17.314(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.127(12)
_cell_angle_gamma                90
_cell_volume                     765.17(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3839
_cell_measurement_temperature    289(13)
_cell_measurement_theta_max      75.9000
_cell_measurement_theta_min      2.5910
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.793
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8494
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         88.491
_diffrn_reflns_theta_min         2.592
_diffrn_ambient_temperature      289.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     60.00 103.00   0.50    1.08    --  108.36-125.00-180.00   86
  2  ω     37.00 105.00   0.50    1.08    --  108.36 -94.00 -60.00  136
  3  ω     74.00 102.00   0.50    1.08    --  108.36 -77.00  30.00   56
  4  ω     38.00  69.00   0.50    1.08    --  108.36 -77.00  30.00   62
  5  ω     41.00  85.00   0.50    1.08    --  108.36 -94.00  30.00   88
  6  ω    -12.00  19.00   0.50    0.27    --   45.08 -29.00-122.00   62
  7  ω     47.00  72.00   0.50    1.08    --  108.36 -61.00-180.00   50
  8  ω     42.00  67.00   0.50    1.08    --  108.36 -61.00 -60.00   50
  9  ω     35.00  66.00   0.50    1.08    --  108.36 -61.00 -30.00   62
 10  ω    -30.00  27.00   0.50    0.27    --   45.08 -19.00  60.00  114
 11  ω     27.00 123.00   0.50    0.27    --   45.08  29.00  38.00  192
 12  ω     54.00  90.00   0.50    0.27    --   45.08  37.00  90.00   72
 13  ω     21.00  89.00   0.50    0.27    --   45.08  77.00  90.00  136
 14  ω     92.00 153.00   0.50    1.08    --  108.36  29.00  38.00  122
 15  ω     27.00  78.00   0.50    0.27    --   45.08  57.00-180.00  102
 16  ω    -16.00  12.00   0.50    0.27    --  -45.08  19.00 -60.00   56
 17  ω    -23.00  26.00   0.50    0.27    --  -45.08  19.00-180.00   98
 18  ω    -66.00 -40.00   0.50    1.08    -- -102.00  61.00-180.00   52
 19  ω    -64.00 -38.00   0.50    1.08    -- -102.00  61.00-150.00   52
 20  ω   -104.00 -41.00   0.50    1.08    -- -102.00  77.00 -60.00  126
 21  ω    -63.00 -37.00   0.50    1.08    -- -102.00  61.00 150.00   52
 22  ω      0.00  25.00   0.50    0.27    --  -45.08  29.00  38.00   50
 23  ω    -74.00 -49.00   0.50    0.27    --  -45.08 -29.00-122.00   50
 24  ω   -101.00 -76.00   0.50    1.08    -- -102.00 -77.00-150.00   50
 25  ω   -104.00 -78.00   0.50    1.08    -- -102.00 -77.00 120.00   52
 26  ω   -101.00 -76.00   0.50    1.08    -- -102.00 -76.00 125.56   50
 27  ω   -102.00 -77.00   0.50    1.08    -- -102.00 -74.00 152.03   50
 28  ω   -104.00 -79.00   0.50    1.08    -- -102.00 -69.00 156.40   50
 29  ω   -103.00 -78.00   0.50    1.08    -- -102.00 -73.00 140.67   50
 30  ω   -108.00 -82.00   0.50    1.08    -- -102.00 -64.00 134.87   52
 31  ω   -175.00-111.00   0.50    1.08    -- -102.00 -76.00 125.56  128
 32  ω   -116.00 -87.00   0.50    1.08    -- -102.00 -61.00 120.00   58
 33  ω   -107.00 -81.00   0.50    1.08    -- -102.00 -64.00-165.15   52
 34  ω   -107.00 -82.00   0.50    1.08    -- -102.00 -61.00-180.00   50
 35  ω   -127.00 -84.00   0.50    1.08    -- -102.00 -61.00-150.00   86
 36  ω   -170.00-122.00   0.50    1.08    -- -102.00 -61.00-180.00   96
 37  ω   -169.00-143.00   0.50    1.08    -- -102.00 -61.00-150.00   52
 38  ω   -155.00-129.00   0.50    1.08    -- -102.00 -58.00  77.92   52
 39  ω   -114.00 -83.00   0.50    1.08    -- -102.00 -58.00  77.92   62
 40  ω   -108.00 -83.00   0.50    1.08    -- -102.00 -61.00  90.00   50
 41  ω   -113.00 -86.00   0.50    1.08    -- -102.00 -52.00 102.95   54
 42  ω   -167.00 -83.00   0.50    1.08    -- -102.00 -50.00  71.84  168
 43  ω   -175.00-134.00   0.50    1.08    -- -102.00 -60.00 172.10   82
 44  ω   -120.00 -84.00   0.50    1.08    -- -102.00 -52.00 153.77   72
 45  ω   -108.00 -83.00   0.50    1.08    -- -102.00 -60.00 172.10   50
 46  ω   -112.00 -84.00   0.50    1.08    -- -102.00 -51.00 141.35   56
 47  ω   -113.00 -87.00   0.50    1.08    -- -102.00 -30.00 150.00   52
 48  ω   -165.00-139.00   0.50    1.08    -- -102.00 -30.00 150.00   52
 49  ω   -126.00 -86.00   0.50    1.08    -- -102.00 -47.00  76.13   80
 50  ω   -129.00 -84.00   0.50    1.08    -- -102.00 -29.00-122.00   90
 51  ω   -130.00 -86.00   0.50    1.08    -- -102.00 -45.00-180.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.885
_reflns_Friedel_fraction_max     0.741
_reflns_number_gt                2191
_reflns_number_total             2874
_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       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 
;
 Flack x determined using 683 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.22(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2874
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0780
_refine_ls_restrained_S_all      1.142
_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)+(0.1461P)²+0.0859P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2212
_refine_ls_wR_factor_ref         0.2520
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C11(H11), C14(H14), C3(H3), C12(H12), C15(H15)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C1(H1D,H1E,H1F)
;
_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
O3 O 0.3633(6) 0.9756(8) 0.1059(2) 0.0877(12) Uani 1 1 d . . . . .
F1 F 0.4917(7) 0.7788(10) 0.46771(18) 0.1284(18) Uani 1 1 d . . . . .
N1 N 0.6131(5) 0.2654(8) 0.0575(2) 0.0698(10) Uani 1 1 d . . . . .
H1A H 0.581134 0.256081 0.005620 0.084 Uiso 1 1 calc R U . . .
H1B H 0.581938 0.395437 0.073331 0.084 Uiso 1 1 calc R U . . .
H1C H 0.553568 0.163606 0.079930 0.084 Uiso 1 1 calc R U . . .
O1 O 0.9973(7) 0.3208(9) 0.4099(2) 0.1017(15) Uani 1 1 d . . . . .
O2 O 0.4917(7) 0.6588(9) 0.1062(2) 0.1055(15) Uani 1 1 d . . . . .
C5 C 0.8757(6) 0.2565(9) 0.1684(3) 0.0665(12) Uani 1 1 d . . . . .
C16 C 0.4254(6) 0.8060(10) 0.1406(3) 0.0708(12) Uani 1 1 d . . . . .
C4 C 0.9686(7) 0.4384(10) 0.2008(3) 0.0781(15) Uani 1 1 d . . . . .
H4 H 1.001491 0.545117 0.167796 0.094 Uiso 1 1 calc R U . . .
C2 C 0.9659(7) 0.3102(10) 0.3306(3) 0.0750(14) Uani 1 1 d . . . . .
C13 C 0.4341(6) 0.7911(9) 0.2278(3) 0.0654(11) Uani 1 1 d . . . . .
C6 C 0.8348(7) 0.0950(10) 0.2189(3) 0.0749(14) Uani 1 1 d . . . . .
H6 H 0.778098 -0.032402 0.198178 0.090 Uiso 1 1 calc R U . . .
C7 C 0.8764(8) 0.1207(10) 0.2981(3) 0.0782(15) Uani 1 1 d . . . . .
H7 H 0.845611 0.012411 0.330938 0.094 Uiso 1 1 calc R U . . .
C8 C 0.8207(7) 0.2336(11) 0.0808(3) 0.0759(14) Uani 1 1 d . . . . .
H8 H 0.883105 0.348817 0.056210 0.091 Uiso 1 1 calc R U . . .
C11 C 0.5366(9) 0.6134(12) 0.3511(3) 0.0874(17) Uani 1 1 d . . . . .
H11 H 0.594440 0.496604 0.379435 0.105 Uiso 1 1 calc R U . . .
C10 C 0.4711(9) 0.7811(13) 0.3884(3) 0.0873(17) Uani 1 1 d . . . . .
C14 C 0.3668(8) 0.9609(10) 0.2678(3) 0.0774(13) Uani 1 1 d . . . . .
H14 H 0.308095 1.077861 0.239865 0.093 Uiso 1 1 calc R U . . .
C3 C 1.0141(8) 0.4662(11) 0.2811(3) 0.0810(15) Uani 1 1 d . . . . .
H3 H 1.077143 0.590122 0.301569 0.097 Uiso 1 1 calc R U . . .
C12 C 0.5167(8) 0.6174(10) 0.2700(3) 0.0772(14) Uani 1 1 d . . . . .
H12 H 0.559553 0.501339 0.243902 0.093 Uiso 1 1 calc R U . . .
C15 C 0.3863(9) 0.9575(12) 0.3484(4) 0.0906(18) Uani 1 1 d . . . . .
H15 H 0.343004 1.071931 0.375195 0.109 Uiso 1 1 calc R U . . .
C9 C 0.8705(10) 0.0203(16) 0.0475(4) 0.109(2) Uani 1 1 d . . . . .
H9A H 0.817928 -0.095984 0.073396 0.163 Uiso 1 1 calc R U . . .
H9B H 1.003875 0.005093 0.055681 0.163 Uiso 1 1 calc R U . . .
H9C H 0.821291 0.015734 -0.007652 0.163 Uiso 1 1 calc R U . . .
C1 C 1.0751(15) 0.5117(18) 0.4464(4) 0.128(3) Uani 1 1 d . . . . .
H1D H 1.184073 0.550894 0.425311 0.192 Uiso 1 1 calc R U . . .
H1E H 1.109358 0.487810 0.501876 0.192 Uiso 1 1 calc R U . . .
H1F H 0.984976 0.626555 0.436960 0.192 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
O3 C16 1.252(7) . ?
F1 C10 1.354(6) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C8 1.505(6) . ?
O1 C2 1.354(6) . ?
O1 C1 1.408(11) . ?
O2 C16 1.230(7) . ?
C5 C4 1.378(8) . ?
C5 C6 1.393(7) . ?
C5 C8 1.506(7) . ?
C16 C13 1.503(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.382(8) . ?
C2 C7 1.407(8) . ?
C2 C3 1.375(8) . ?
C13 C14 1.392(8) . ?
C13 C12 1.375(8) . ?
C6 H6 0.9300 . ?
C6 C7 1.361(7) . ?
C7 H7 0.9300 . ?
C8 H8 0.9800 . ?
C8 C9 1.507(10) . ?
C11 H11 0.9300 . ?
C11 C10 1.352(10) . ?
C11 C12 1.385(8) . ?
C10 C15 1.377(10) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(8) . ?
C3 H3 0.9300 . ?
C12 H12 0.9300 . ?
C15 H15 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C1 H1F 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
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C8 N1 H1A 109.5 . . ?
C8 N1 H1B 109.5 . . ?
C8 N1 H1C 109.5 . . ?
C2 O1 C1 118.6(6) . . ?
C4 C5 C6 118.2(4) . . ?
C4 C5 C8 120.7(5) . . ?
C6 C5 C8 121.1(5) . . ?
O3 C16 C13 118.8(5) . . ?
O2 C16 O3 121.7(5) . . ?
O2 C16 C13 119.3(5) . . ?
C5 C4 H4 119.2 . . ?
C5 C4 C3 121.6(5) . . ?
C3 C4 H4 119.2 . . ?
O1 C2 C7 115.4(5) . . ?
O1 C2 C3 125.6(5) . . ?
C3 C2 C7 118.9(5) . . ?
C14 C13 C16 119.9(5) . . ?
C12 C13 C16 121.2(5) . . ?
C12 C13 C14 118.8(5) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 121.0(5) . . ?
C7 C6 H6 119.5 . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.3(5) . . ?
C6 C7 H7 119.8 . . ?
N1 C8 C5 109.5(3) . . ?
N1 C8 H8 107.9 . . ?
N1 C8 C9 108.0(5) . . ?
C5 C8 H8 107.9 . . ?
C5 C8 C9 115.3(5) . . ?
C9 C8 H8 107.9 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.2(6) . . ?
C12 C11 H11 120.4 . . ?
F1 C10 C15 118.6(6) . . ?
C11 C10 F1 119.4(6) . . ?
C11 C10 C15 122.0(5) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.7(6) . . ?
C15 C14 H14 119.7 . . ?
C4 C3 H3 120.1 . . ?
C2 C3 C4 119.9(5) . . ?
C2 C3 H3 120.1 . . ?
C13 C12 C11 120.7(6) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C10 C15 C14 118.6(6) . . ?
C10 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
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 . . ?
O1 C1 H1D 109.5 . . ?
O1 C1 H1E 109.5 . . ?
O1 C1 H1F 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?

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
_geom_hbond_publ_flag
N1 H1A O3 0.89 2.45 3.145(6) 135.2 2_645 yes
N1 H1A O2 0.89 2.01 2.880(6) 166.3 2_645 yes
N1 H1B O2 0.89 1.88 2.766(7) 174.2 . yes
N1 H1C O3 0.89 1.92 2.781(6) 162.8 1_545 yes
C8 H8 O3 0.98 3.15 3.598(7) 109.4 2_645 yes
C14 H14 O3 0.93 2.50 2.801(6) 98.8 . yes
C12 H12 O2 0.93 2.54 2.822(6) 97.8 . yes
C9 H9B O3 0.96 2.61 3.559(8) 169.1 1_645 yes
C9 H9C O2 0.96 2.74 3.506(9) 137.2 2_645 yes
C1 H1D F1 0.96 2.64 3.412(12) 138.2 1_655 yes
C1 H1E F1 0.96 3.13 3.543(12) 107.5 2_746 yes
C1 H1E O1 0.96 2.75 3.251(10) 113.0 2_756 yes

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
O3 C16 C13 C14 2.5(7) . . . . ?
O3 C16 C13 C12 -173.9(5) . . . . ?
F1 C10 C15 C14 179.4(5) . . . . ?
O1 C2 C7 C6 178.7(5) . . . . ?
O1 C2 C3 C4 -178.0(5) . . . . ?
O2 C16 C13 C14 177.3(5) . . . . ?
O2 C16 C13 C12 0.8(7) . . . . ?
C5 C4 C3 C2 -0.2(9) . . . . ?
C5 C6 C7 C2 -1.4(8) . . . . ?
C16 C13 C14 C15 -175.1(5) . . . . ?
C16 C13 C12 C11 175.0(5) . . . . ?
C4 C5 C6 C7 3.4(8) . . . . ?
C4 C5 C8 N1 -106.4(5) . . . . ?
C4 C5 C8 C9 131.6(6) . . . . ?
C13 C14 C15 C10 -1.0(9) . . . . ?
C6 C5 C4 C3 -2.6(8) . . . . ?
C6 C5 C8 N1 73.7(6) . . . . ?
C6 C5 C8 C9 -48.3(6) . . . . ?
C7 C2 C3 C4 2.2(9) . . . . ?
C8 C5 C4 C3 177.5(5) . . . . ?
C8 C5 C6 C7 -176.7(5) . . . . ?
C11 C10 C15 C14 0.6(10) . . . . ?
C10 C11 C12 C13 1.1(9) . . . . ?
C14 C13 C12 C11 -1.5(8) . . . . ?
C3 C2 C7 C6 -1.5(9) . . . . ?
C12 C13 C14 C15 1.5(8) . . . . ?
C12 C11 C10 F1 -179.4(5) . . . . ?
C12 C11 C10 C15 -0.6(9) . . . . ?
C1 O1 C2 C7 -175.9(7) . . . . ?
C1 O1 C2 C3 4.3(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_zn-240130-6hs_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2kfxyw
_database_code_depnum_ccdc_archive 'CCDC 2366879'
loop_
_audit_author_name
_audit_author_address
MaoWeiXin
;NanChang University
China
;
_audit_update_record             
;
2024-07-01 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;
_audit_creation_date             2024-07-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H14 N O, C7 H5 O2'
_chemical_formula_sum            'C16 H19 N O3'
_chemical_formula_weight         273.32
_chemical_absolute_configuration syn
_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'
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      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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.1046(2)
_cell_length_b                   7.3469(2)
_cell_length_c                   33.6375(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1508.64(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2632
_cell_measurement_temperature    298.7(9)
_cell_measurement_theta_max      73.4180
_cell_measurement_theta_min      2.6110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            4665
_diffrn_reflns_point_group_measured_fraction_full 0.908
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.359
_diffrn_reflns_theta_min         2.627
_diffrn_ambient_temperature      299.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00 -31.00   0.50    0.45    -- -102.00 107.00-133.00  106
  2  ω    -69.00 -28.00   0.50    0.45    -- -102.00  61.00  30.00   82
  3  ω   -120.00 -32.00   0.50    0.20    --  -45.08 -18.00 -96.00  176
  4  ω     47.00  88.00   0.50    0.20    --   45.08-125.00 -30.00   82
  5  ω     76.00 102.00   0.50    0.45    --  108.36-129.00  50.00   52
  6  ω     76.00 103.00   0.50    0.45    --  108.36 -94.00 120.00   54
  7  ω     92.00 162.00   0.50    0.45    --  108.36  18.00  71.00  140
  8  ω     92.00 142.00   0.50    0.45    --  108.36  30.00 150.00  100
  9  ω    -18.00  27.00   0.50    0.20    --   45.08 -19.00 120.00   90
 10  ω     39.00  64.00   0.50    0.45    --  108.36 -61.00-150.00   50
 11  ω     43.00  70.00   0.50    0.45    --  108.36 -61.00-180.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.499
_reflns_Friedel_fraction_full    0.778
_reflns_Friedel_fraction_max     0.697
_reflns_number_gt                2359
_reflns_number_total             2684
_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       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 728 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2684
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      1.050
_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)+(0.0873P)²+0.1292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1471
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C4(H4), C5(H5), C7(H7), C16(H16), C12(H12), C15(H15), C13(H13),
 C14(H14)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C1(H1D,H1E,H1F), C9(H9A,H9B,H9C)
;
_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
O3 O 0.4377(4) 0.5609(4) 0.71034(6) 0.0944(7) Uani 1 1 d . . . . .
O2 O 1.1003(4) 0.0631(4) 0.55262(6) 0.0925(7) Uani 1 1 d . . . . .
N1 N 0.3842(4) 0.3428(3) 0.53048(5) 0.0691(6) Uani 1 1 d . . . . .
H1A H 0.383490 0.335622 0.504066 0.083 Uiso 1 1 calc R U . . .
H1B H 0.277658 0.273458 0.540309 0.083 Uiso 1 1 calc R U . . .
H1C H 0.512800 0.304293 0.539693 0.083 Uiso 1 1 calc R U . . .
O1 O 0.7842(4) 0.1940(4) 0.55164(6) 0.1075(9) Uani 1 1 d . . . . .
C10 C 0.9305(5) 0.1104(4) 0.56939(8) 0.0688(7) Uani 1 1 d . . . . .
C11 C 0.9076(4) 0.0806(3) 0.61371(7) 0.0612(6) Uani 1 1 d . . . . .
C6 C 0.4253(5) 0.5654(4) 0.66949(7) 0.0685(7) Uani 1 1 d . . . . .
C8 C 0.5545(5) 0.6306(4) 0.60426(8) 0.0707(7) Uani 1 1 d . . . . .
H8 H 0.661959 0.678595 0.587697 0.085 Uiso 1 1 calc R U . . .
C3 C 0.3713(4) 0.5521(3) 0.58763(7) 0.0628(6) Uani 1 1 d . . . . .
C4 C 0.2122(5) 0.4836(4) 0.61285(8) 0.0710(7) Uani 1 1 d . . . . .
H4 H 0.085301 0.433265 0.602202 0.085 Uiso 1 1 calc R U . . .
C5 C 0.2391(5) 0.4887(4) 0.65330(8) 0.0736(8) Uani 1 1 d . . . . .
H5 H 0.131753 0.440546 0.669851 0.088 Uiso 1 1 calc R U . . .
C7 C 0.5827(5) 0.6398(4) 0.64516(8) 0.0746(7) Uani 1 1 d . . . . .
H7 H 0.706063 0.695319 0.655935 0.090 Uiso 1 1 calc R U . . .
C2 C 0.3485(5) 0.5363(4) 0.54287(8) 0.0726(8) Uani 1 1 d . . . . .
H2 H 0.463359 0.610722 0.530633 0.087 Uiso 1 1 calc R U . . .
C16 C 1.0696(5) -0.0089(4) 0.63407(8) 0.0730(7) Uani 1 1 d . . . . .
H16 H 1.187061 -0.059422 0.620354 0.088 Uiso 1 1 calc R U . . .
C12 C 0.7314(5) 0.1505(5) 0.63424(8) 0.0780(8) Uani 1 1 d . . . . .
H12 H 0.618041 0.207356 0.620566 0.094 Uiso 1 1 calc R U . . .
C15 C 1.0583(7) -0.0241(5) 0.67503(9) 0.0895(10) Uani 1 1 d . . . . .
H15 H 1.168308 -0.084550 0.688869 0.107 Uiso 1 1 calc R U . . .
C13 C 0.7233(7) 0.1361(5) 0.67511(10) 0.0959(11) Uani 1 1 d . . . . .
H13 H 0.605845 0.186082 0.688923 0.115 Uiso 1 1 calc R U . . .
C14 C 0.8843(8) 0.0503(5) 0.69521(9) 0.0984(11) Uani 1 1 d . . . . .
H14 H 0.877440 0.041506 0.722764 0.118 Uiso 1 1 calc R U . . .
C1 C 0.1304(7) 0.5994(6) 0.52671(10) 0.1047(13) Uani 1 1 d . . . . .
H1D H 0.131816 0.591748 0.498220 0.157 Uiso 1 1 calc R U . . .
H1E H 0.104939 0.723115 0.534620 0.157 Uiso 1 1 calc R U . . .
H1F H 0.015840 0.523293 0.537021 0.157 Uiso 1 1 calc R U . . .
C9 C 0.6369(7) 0.6134(8) 0.72787(10) 0.1204(16) Uani 1 1 d . . . . .
H9A H 0.666760 0.738343 0.721497 0.181 Uiso 1 1 calc R U . . .
H9B H 0.752912 0.538013 0.717883 0.181 Uiso 1 1 calc R U . . .
H9C H 0.626968 0.599768 0.756193 0.181 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
O3 C6 1.377(3) . ?
O3 C9 1.405(5) . ?
O2 C10 1.230(4) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C2 1.498(4) . ?
O1 C10 1.237(4) . ?
C10 C11 1.513(3) . ?
C11 C16 1.371(4) . ?
C11 C12 1.377(4) . ?
C6 C5 1.380(4) . ?
C6 C7 1.376(4) . ?
C8 H8 0.9300 . ?
C8 C3 1.377(4) . ?
C8 C7 1.388(4) . ?
C3 C4 1.385(4) . ?
C3 C2 1.516(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.371(4) . ?
C5 H5 0.9300 . ?
C7 H7 0.9300 . ?
C2 H2 0.9800 . ?
C2 C1 1.511(5) . ?
C16 H16 0.9300 . ?
C16 C15 1.384(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.374(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.349(5) . ?
C14 H14 0.9300 . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C1 H1F 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
C6 O3 C9 117.4(3) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
O2 C10 O1 121.8(3) . . ?
O2 C10 C11 119.3(3) . . ?
O1 C10 C11 118.7(3) . . ?
C16 C11 C10 119.7(2) . . ?
C16 C11 C12 119.5(2) . . ?
C12 C11 C10 120.8(2) . . ?
O3 C6 C5 115.4(3) . . ?
C7 C6 O3 124.4(3) . . ?
C7 C6 C5 120.2(2) . . ?
C3 C8 H8 119.2 . . ?
C3 C8 C7 121.6(2) . . ?
C7 C8 H8 119.2 . . ?
C8 C3 C4 118.2(2) . . ?
C8 C3 C2 120.7(2) . . ?
C4 C3 C2 121.1(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 120.9(3) . . ?
C5 C4 H4 119.5 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C7 C8 118.9(3) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
N1 C2 C3 109.6(2) . . ?
N1 C2 H2 108.0 . . ?
N1 C2 C1 108.6(3) . . ?
C3 C2 H2 108.0 . . ?
C1 C2 C3 114.5(3) . . ?
C1 C2 H2 108.0 . . ?
C11 C16 H16 120.0 . . ?
C11 C16 C15 120.0(3) . . ?
C15 C16 H16 120.0 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 119.9(3) . . ?
C13 C12 H12 120.0 . . ?
C16 C15 H15 120.1 . . ?
C14 C15 C16 119.9(3) . . ?
C14 C15 H15 120.1 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.1(3) . . ?
C13 C14 H14 120.0 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
_geom_hbond_publ_flag
N1 H1A O1 0.89 1.98 2.842(3) 162.2 4_456 yes
N1 H1B O2 0.89 1.93 2.789(4) 161.3 1_455 yes
N1 H1C O1 0.89 1.89 2.768(3) 169.9 . yes

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
O3 C6 C5 C4 -179.0(3) . . . . ?
O3 C6 C7 C8 177.9(3) . . . . ?
O2 C10 C11 C16 -4.2(4) . . . . ?
O2 C10 C11 C12 172.4(3) . . . . ?
O1 C10 C11 C16 -178.9(3) . . . . ?
O1 C10 C11 C12 -2.3(4) . . . . ?
C10 C11 C16 C15 174.9(3) . . . . ?
C10 C11 C12 C13 -174.1(3) . . . . ?
C11 C16 C15 C14 0.1(5) . . . . ?
C11 C12 C13 C14 -1.5(6) . . . . ?
C8 C3 C4 C5 -1.9(4) . . . . ?
C8 C3 C2 N1 105.8(3) . . . . ?
C8 C3 C2 C1 -131.8(3) . . . . ?
C3 C8 C7 C6 1.2(5) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C4 C3 C2 N1 -72.3(4) . . . . ?
C4 C3 C2 C1 50.1(4) . . . . ?
C5 C6 C7 C8 -2.2(5) . . . . ?
C7 C6 C5 C4 1.2(4) . . . . ?
C7 C8 C3 C4 0.8(4) . . . . ?
C7 C8 C3 C2 -177.4(3) . . . . ?
C2 C3 C4 C5 176.2(3) . . . . ?
C16 C11 C12 C13 2.5(5) . . . . ?
C16 C15 C14 C13 0.8(6) . . . . ?
C12 C11 C16 C15 -1.8(4) . . . . ?
C12 C13 C14 C15 -0.1(6) . . . . ?
C9 O3 C6 C5 171.2(3) . . . . ?
C9 O3 C6 C7 -9.0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_zn-240130-1-2_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2kfxwt
_database_code_depnum_ccdc_archive 'CCDC 2366877'
loop_
_audit_author_name
_audit_author_address
MaoWeiXin
;NanChang University
China
;
_audit_update_record             
;
2024-07-01 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;
_audit_creation_date             2024-06-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H4 F O2, C9 H14 N O'
_chemical_formula_sum            'C16 H18 F N O3'
_chemical_formula_weight         291.31
_chemical_absolute_configuration syn
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.2820(2)
_cell_length_b                   6.1726(2)
_cell_length_c                   17.3070(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.162(2)
_cell_angle_gamma                90
_cell_volume                     765.73(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2441
_cell_measurement_temperature    296.23(10)
_cell_measurement_theta_max      72.7430
_cell_measurement_theta_min      2.5890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4316
_diffrn_reflns_point_group_measured_fraction_full 0.820
_diffrn_reflns_point_group_measured_fraction_max 0.754
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.673
_diffrn_reflns_theta_min         2.594
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     46.00  75.00   0.50    1.60    --  108.36 -94.00-180.00   58
  2  ω     20.00  93.00   0.50    0.50    --   45.20-125.00-180.00  146
  3  ω    -31.00  -6.00   0.50    0.50    --  -45.20  54.00  49.00   50
  4  ω    -66.00 -29.00   0.50    1.60    -- -102.00  61.00   0.00   74
  5  ω    -56.00 -28.00   0.50    1.60    -- -102.00  54.00  49.00   56
  6  ω   -171.00-119.00   0.50    1.60    -- -102.00 -15.00 150.00  104
  7  ω   -115.00 -89.00   0.50    1.60    -- -102.00 -15.00 150.00   52
  8  ω   -117.00 -84.00   0.50    1.60    -- -102.00 -45.00 -30.00   66
  9  ω   -174.00-127.00   0.50    1.60    -- -102.00 -45.00 -30.00   94
 10  ω   -175.00 -84.00   0.50    1.60    -- -102.00 -54.00 -93.00  182
 11  ω    -95.00 -70.00   0.50    0.50    --  -45.20 -54.00 -93.00   50
 12  ω    -26.00  61.00   0.50    0.50    --   45.20 -54.00 -93.00  174
 13  ω     35.00  89.00   0.50    1.60    --  108.36 -77.00  60.00  108
 14  ω     43.00  68.00   0.50    1.60    --  108.36 -61.00 120.00   50
 15  ω     36.00  63.00   0.50    1.60    --  108.36 -61.00  60.00   54
 16  ω     35.00  60.00   0.50    1.60    --  108.36 -61.00 -60.00   50
 17  ω     38.00  63.00   0.50    1.60    --  108.36 -54.00 -93.00   50
 18  ω     35.00  60.00   0.50    1.60    --  108.36 -61.00-150.00   50
 19  ω     27.00 116.00   0.50    0.50    --   45.20  54.00  49.00  178
 20  ω     97.00 126.00   0.50    1.60    --  108.36  30.00 150.00   58
 21  ω    142.00 178.00   0.50    1.60    --  108.36  30.00 150.00   72
 22  ω    153.00 178.00   0.50    1.60    --  108.36  54.00  49.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.484
_reflns_Friedel_fraction_full    0.614
_reflns_Friedel_fraction_max     0.545
_reflns_number_gt                2048
_reflns_number_total             2422
_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       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 622 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.13(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2422
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0600
_refine_ls_restrained_S_all      1.081
_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)+(0.1376P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1807
_refine_ls_wR_factor_ref         0.1902
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C2(H2)
1.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C4(H4), C7(H7), C14(H14), C11(H11), C12(H12), C15(H15)
1.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C1(H1D,H1E,H1F), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O3 O 0.3632(4) 0.0198(6) 0.10555(16) 0.0813(9) Uani 1 1 d . . . . .
F1 F 0.4910(5) 0.2142(8) 0.46763(13) 0.1223(14) Uani 1 1 d . . . . .
N1 N 0.6139(4) 0.7296(6) 0.05740(14) 0.0625(8) Uani 1 1 d . . . . .
H1A H 0.582692 0.734353 0.005341 0.075 Uiso 1 1 calc R U . . .
H1B H 0.554382 0.834203 0.078381 0.075 Uiso 1 1 calc R U . . .
H1C H 0.582085 0.601526 0.074633 0.075 Uiso 1 1 calc R U . . .
O1 O 0.9959(5) 0.6731(8) 0.41009(15) 0.0993(12) Uani 1 1 d . . . . .
O2 O 0.4912(5) 0.3365(7) 0.10608(18) 0.0998(12) Uani 1 1 d . . . . .
C16 C 0.4252(4) 0.1872(7) 0.1406(2) 0.0650(9) Uani 1 1 d . . . . .
C8 C 0.9693(5) 0.5568(7) 0.2010(2) 0.0694(10) Uani 1 1 d . . . . .
H8 H 1.002429 0.450294 0.167978 0.083 Uiso 1 1 calc R U . . .
C13 C 0.4329(4) 0.2013(7) 0.22772(19) 0.0582(8) Uani 1 1 d . . . . .
C3 C 0.8761(4) 0.7377(7) 0.16851(18) 0.0611(9) Uani 1 1 d . . . . .
C5 C 0.8752(5) 0.8709(9) 0.2982(2) 0.0743(11) Uani 1 1 d . . . . .
H5 H 0.843146 0.977608 0.331326 0.089 Uiso 1 1 calc R U . . .
C4 C 0.8340(5) 0.8991(8) 0.2188(2) 0.0688(10) Uani 1 1 d . . . . .
H4 H 0.777645 1.026802 0.198208 0.083 Uiso 1 1 calc R U . . .
C2 C 0.8203(5) 0.7612(8) 0.0807(2) 0.0701(11) Uani 1 1 d . . . . .
H2 H 0.882494 0.646132 0.056020 0.084 Uiso 1 1 calc R U . . .
C6 C 0.9648(4) 0.6834(8) 0.3299(2) 0.0686(10) Uani 1 1 d . . . . .
C7 C 1.0149(5) 0.5291(8) 0.2810(2) 0.0720(10) Uani 1 1 d . . . . .
H7 H 1.079375 0.406073 0.301601 0.086 Uiso 1 1 calc R U . . .
C14 C 0.3663(5) 0.0332(8) 0.2679(2) 0.0683(9) Uani 1 1 d . . . . .
H14 H 0.308192 -0.084127 0.239981 0.082 Uiso 1 1 calc R U . . .
C10 C 0.4715(6) 0.2120(10) 0.3884(2) 0.0822(13) Uani 1 1 d . . . . .
C11 C 0.5364(6) 0.3822(9) 0.3514(2) 0.0816(13) Uani 1 1 d . . . . .
H11 H 0.592626 0.499654 0.379841 0.098 Uiso 1 1 calc R U . . .
C12 C 0.5171(5) 0.3771(8) 0.2701(2) 0.0707(10) Uani 1 1 d . . . . .
H12 H 0.560781 0.492296 0.243829 0.085 Uiso 1 1 calc R U . . .
C15 C 0.3846(6) 0.0362(10) 0.3485(3) 0.0844(13) Uani 1 1 d . . . . .
H15 H 0.339466 -0.077137 0.375257 0.101 Uiso 1 1 calc R U . . .
C1 C 0.8712(7) 0.9755(13) 0.0478(3) 0.1030(19) Uani 1 1 d . . . . .
H1D H 0.824267 0.979821 -0.007628 0.155 Uiso 1 1 calc R U . . .
H1E H 1.004411 0.991161 0.056952 0.155 Uiso 1 1 calc R U . . .
H1F H 0.817109 1.091582 0.073125 0.155 Uiso 1 1 calc R U . . .
C9 C 1.0740(12) 0.4849(15) 0.4470(3) 0.128(3) Uani 1 1 d . . . . .
H9A H 1.184351 0.447324 0.426746 0.191 Uiso 1 1 calc R U . . .
H9B H 0.985452 0.368655 0.437119 0.191 Uiso 1 1 calc R U . . .
H9C H 1.105985 0.509534 0.502532 0.191 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
O3 C16 1.242(5) . ?
F1 C10 1.353(4) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C2 1.499(4) . ?
O1 C6 1.368(4) . ?
O1 C9 1.398(9) . ?
O2 C16 1.240(5) . ?
C16 C13 1.501(4) . ?
C8 H8 0.9300 . ?
C8 C3 1.374(6) . ?
C8 C7 1.377(5) . ?
C13 C14 1.384(6) . ?
C13 C12 1.390(6) . ?
C3 C4 1.392(6) . ?
C3 C2 1.509(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.364(5) . ?
C5 C6 1.393(6) . ?
C4 H4 0.9300 . ?
C2 H2 0.9800 . ?
C2 C1 1.512(8) . ?
C6 C7 1.366(6) . ?
C7 H7 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.378(6) . ?
C10 C11 1.358(8) . ?
C10 C15 1.379(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(5) . ?
C12 H12 0.9300 . ?
C15 H15 0.9300 . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C1 H1F 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
C6 O1 C9 118.9(4) . . ?
O3 C16 C13 119.0(3) . . ?
O2 C16 O3 121.4(3) . . ?
O2 C16 C13 119.5(4) . . ?
C3 C8 H8 119.1 . . ?
C3 C8 C7 121.8(4) . . ?
C7 C8 H8 119.1 . . ?
C14 C13 C16 120.4(3) . . ?
C14 C13 C12 118.8(3) . . ?
C12 C13 C16 120.7(3) . . ?
C8 C3 C4 118.3(3) . . ?
C8 C3 C2 121.0(4) . . ?
C4 C3 C2 120.7(4) . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.5(4) . . ?
C6 C5 H5 119.8 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4 119.9 . . ?
N1 C2 C3 109.7(3) . . ?
N1 C2 H2 107.9 . . ?
N1 C2 C1 108.2(3) . . ?
C3 C2 H2 107.9 . . ?
C3 C2 C1 115.0(4) . . ?
C1 C2 H2 107.9 . . ?
O1 C6 C5 114.9(4) . . ?
C7 C6 O1 125.6(4) . . ?
C7 C6 C5 119.5(3) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 C8 119.5(4) . . ?
C6 C7 H7 120.2 . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.3(4) . . ?
C15 C14 H14 119.4 . . ?
F1 C10 C11 119.1(5) . . ?
F1 C10 C15 118.2(5) . . ?
C11 C10 C15 122.7(4) . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.6(4) . . ?
C12 C11 H11 120.7 . . ?
C13 C12 H12 119.7 . . ?
C11 C12 C13 120.6(4) . . ?
C11 C12 H12 119.7 . . ?
C14 C15 C10 118.1(4) . . ?
C14 C15 H15 120.9 . . ?
C10 C15 H15 120.9 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
_geom_hbond_publ_flag
N1 H1A O3 0.89 2.42 3.134(4) 137.4 2_655 yes
N1 H1A O2 0.89 2.01 2.874(4) 163.5 2_655 yes
N1 H1B O3 0.89 1.92 2.788(5) 163.1 1_565 yes
N1 H1C O2 0.89 1.88 2.768(5) 174.5 . yes
C2 H2 O3 0.98 3.14 3.589(5) 109.5 2_655 yes
C14 H14 O3 0.93 2.51 2.807(5) 98.6 . yes
C12 H12 O2 0.93 2.54 2.823(5) 98.1 . yes
C1 H1D O2 0.96 2.75 3.509(6) 136.1 2_655 yes
C1 H1E O3 0.96 2.61 3.556(5) 170.7 1_665 yes
C9 H9A F1 0.96 2.65 3.429(9) 139.0 1_655 yes
C9 H9C F1 0.96 3.15 3.545(9) 106.4 2_756 yes
C9 H9C O1 0.96 2.75 3.244(8) 113.0 2_746 yes

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
O3 C16 C13 C14 -2.1(5) . . . . ?
O3 C16 C13 C12 174.0(3) . . . . ?
F1 C10 C11 C12 179.4(4) . . . . ?
F1 C10 C15 C14 -179.4(4) . . . . ?
O1 C6 C7 C8 177.8(4) . . . . ?
O2 C16 C13 C14 -177.6(4) . . . . ?
O2 C16 C13 C12 -1.6(5) . . . . ?
C16 C13 C14 C15 175.2(3) . . . . ?
C16 C13 C12 C11 -175.2(3) . . . . ?
C8 C3 C4 C5 -3.8(5) . . . . ?
C8 C3 C2 N1 106.6(4) . . . . ?
C8 C3 C2 C1 -131.1(4) . . . . ?
C13 C14 C15 C10 -0.1(6) . . . . ?
C3 C8 C7 C6 0.8(6) . . . . ?
C5 C6 C7 C8 -2.6(6) . . . . ?
C4 C3 C2 N1 -73.4(5) . . . . ?
C4 C3 C2 C1 49.0(4) . . . . ?
C4 C5 C6 O1 -179.1(4) . . . . ?
C4 C5 C6 C7 1.3(6) . . . . ?
C2 C3 C4 C5 176.1(4) . . . . ?
C6 C5 C4 C3 2.0(6) . . . . ?
C7 C8 C3 C4 2.4(6) . . . . ?
C7 C8 C3 C2 -177.5(3) . . . . ?
C14 C13 C12 C11 1.0(5) . . . . ?
C10 C11 C12 C13 0.0(6) . . . . ?
C11 C10 C15 C14 1.1(7) . . . . ?
C12 C13 C14 C15 -0.9(5) . . . . ?
C15 C10 C11 C12 -1.1(7) . . . . ?
C9 O1 C6 C5 175.9(5) . . . . ?
C9 O1 C6 C7 -4.6(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_zn-240130-1-340k_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2kfy21
_database_code_depnum_ccdc_archive 'CCDC 2366883'
loop_
_audit_author_name
_audit_author_address
MaoWeiXin
;NanChang University
China
;
_audit_update_record             
;
2024-07-01 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;
_audit_creation_date             2024-07-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H4 F O2, C9 H14 N O'
_chemical_formula_sum            'C16 H18 F N O3'
_chemical_formula_weight         291.31
_chemical_absolute_configuration syn
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.2717(9)
_cell_length_b                   6.3005(13)
_cell_length_c                   17.295(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.245(12)
_cell_angle_gamma                90
_cell_volume                     782.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2179
_cell_measurement_temperature    339.97(11)
_cell_measurement_theta_max      74.2770
_cell_measurement_theta_min      2.5690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3788
_diffrn_reflns_point_group_measured_fraction_full 0.700
_diffrn_reflns_point_group_measured_fraction_max 0.599
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         85.012
_diffrn_reflns_theta_min         2.588
_diffrn_ambient_temperature      340.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 -28.00   0.50    1.20    -- -102.00  61.00 -60.00   82
  2  ω    -66.00 -28.00   0.50    1.20    -- -102.00  61.00   0.00   76
  3  ω   -104.00 -52.00   0.50    1.20    -- -102.00  77.00  60.00  104
  4  ω    -60.00 -28.00   0.50    1.20    -- -102.00  61.00 120.00   64
  5  ω    -64.00 -37.00   0.50    1.20    -- -102.00  61.00 150.00   54
  6  ω    -23.00  33.00   0.50    0.40    --  -44.95  19.00 150.00  112
  7  ω    -26.00  31.00   0.50    0.40    --  -44.95  40.00   2.00  114
  8  ω    -66.00 -41.00   0.50    1.20    -- -102.00  61.00 -30.00   50
  9  ω   -120.00 -31.00   0.50    0.40    --  -44.95 -40.00-151.00  178
 10  ω   -169.00 -84.00   0.50    1.20    -- -102.00 -40.00-151.00  170
 11  ω     57.00  96.00   0.50    0.40    --   44.95  40.00   2.00   78
 12  ω    102.00 127.00   0.50    1.20    --  108.36  40.00   2.00   50
 13  ω    142.00 178.00   0.50    1.20    --  108.36  30.00  90.00   72
 14  ω    100.00 136.00   0.50    1.20    --  108.36  30.00  90.00   72
 15  ω     51.00 108.00   0.50    1.20    --  108.36 -77.00  90.00  114
 16  ω     37.00  63.00   0.50    1.20    --  108.36 -61.00 150.00   52
 17  ω     35.00  70.00   0.50    1.20    --  108.36 -61.00 -30.00   70
 18  ω      8.00  47.00   0.50    0.40    --   44.95 -40.00-151.00   78
 19  ω     36.00  73.00   0.50    1.20    --  108.36 -61.00-150.00   74
 20  ω     38.00  74.00   0.50    1.20    --  108.36 -94.00-150.00   72
 21  ω     39.00  65.00   0.50    1.20    --  108.36-125.00-180.00   52
 22  ω     81.00 107.00   0.50    1.20    --  108.36-125.00-180.00   52
 23  ω     78.00 105.00   0.50    1.20    --  108.36 -94.00-150.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.306
_reflns_Friedel_fraction_full    0.383
_reflns_Friedel_fraction_max     0.309
_reflns_number_gt                1573
_reflns_number_total             2123
_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       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 399 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2123
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0878
_refine_ls_restrained_S_all      1.190
_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)+(0.1318P)²+0.3701P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2715
_refine_ls_wR_factor_ref         0.2987
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C15-C10
 1.39 with sigma of 0.001
 C14-C13
 1.39 with sigma of 0.001
 C15-C14
 1.39 with sigma of 0.001
 C13-C12
 1.39 with sigma of 0.001
 C11-C12
 1.39 with sigma of 0.001
 C2-C1
 1.47 with sigma of 0.001
 C6-C7
 1.39 with sigma of 0.001
 C5-C4
 1.39 with sigma of 0.001
 C3-C4
 1.39 with sigma of 0.001
 C7-C8
 1.39 with sigma of 0.001
 C5-C6
 1.39 with sigma of 0.001
 C8-C3
 1.39 with sigma of 0.001
 C13-C16
 1.47 with sigma of 0.001
 C2-C3
 1.47 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C2(H2)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C14(H14), C7(H7), C8(H8), C15(H15), C11(H11), C12(H12)
4.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C1(H1D,H1E,H1F), C9(H9A,H9B,H9C)
;
_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
O3 O 0.3781(9) 0.0556(16) 0.1000(3) 0.124(3) Uani 1 1 d . . . . .
N1 N 0.6149(8) 0.7358(16) 0.0590(3) 0.098(2) Uani 1 1 d . . . . .
H1A H 0.587733 0.742875 0.007004 0.118 Uiso 1 1 calc R U . . .
H1B H 0.557565 0.840696 0.080034 0.118 Uiso 1 1 calc R U . . .
H1C H 0.576819 0.611677 0.075237 0.118 Uiso 1 1 calc R U . . .
C16 C 0.4239(9) 0.211(2) 0.1405(3) 0.107(3) Uani 1 1 d D . . . .
O1 O 0.9808(11) 0.6500(17) 0.4111(3) 0.142(3) Uani 1 1 d . . . . .
F1 F 0.4676(10) 0.165(2) 0.4637(3) 0.194(4) Uani 1 1 d . U . . .
O2 O 0.4690(13) 0.374(2) 0.1098(4) 0.177(4) Uani 1 1 d . . . . .
C13 C 0.4269(8) 0.2034(10) 0.2257(3) 0.087(2) Uani 1 1 d D . . . .
C4 C 0.8281(11) 0.8841(12) 0.2209(3) 0.100(3) Uani 1 1 d D . . . .
H4 H 0.772843 1.010407 0.201463 0.120 Uiso 1 1 calc R U . . .
C5 C 0.8663(12) 0.8519(13) 0.3014(3) 0.115(3) Uani 1 1 d D . . . .
H5 H 0.832586 0.954122 0.335274 0.137 Uiso 1 1 calc R U . . .
C6 C 0.9548(10) 0.6669(12) 0.3312(4) 0.111(4) Uani 1 1 d D . . . .
C14 C 0.5043(11) 0.3681(12) 0.2736(3) 0.110(3) Uani 1 1 d D . . . .
H14 H 0.546797 0.489302 0.251382 0.132 Uiso 1 1 calc R U . . .
C3 C 0.8712(9) 0.7303(11) 0.1691(3) 0.099(3) Uani 1 1 d D . . . .
C7 C 1.0058(12) 0.5133(14) 0.2811(3) 0.113(3) Uani 1 1 d D . . . .
H7 H 1.066533 0.389923 0.300522 0.136 Uiso 1 1 calc R U . . .
C8 C 0.9632(11) 0.5495(12) 0.2009(4) 0.119(4) Uani 1 1 d D . . . .
H8 H 0.997987 0.447937 0.167007 0.143 Uiso 1 1 calc R U . . .
C15 C 0.5186(13) 0.3531(17) 0.3545(3) 0.133(4) Uani 1 1 d D . . . .
H15 H 0.570158 0.462826 0.386919 0.159 Uiso 1 1 calc R U . . .
C2 C 0.8218(10) 0.7562(15) 0.0838(3) 0.098(3) Uani 1 1 d D . . . .
H2 H 0.881367 0.640814 0.058897 0.117 Uiso 1 1 calc R U . . .
C10 C 0.4537(13) 0.1696(17) 0.3857(5) 0.136(6) Uani 1 1 d D . . . .
C11 C 0.3725(13) 0.016(2) 0.3410(4) 0.127(4) Uani 1 1 d D . . . .
H11 H 0.321970 -0.099554 0.363787 0.153 Uiso 1 1 calc R U . . .
C12 C 0.3620(10) 0.0251(11) 0.2602(4) 0.104(3) Uani 1 1 d D . . . .
H12 H 0.311566 -0.087898 0.229166 0.125 Uiso 1 1 calc R U . . .
C1 C 0.8785(14) 0.9576(17) 0.0516(6) 0.147(5) Uani 1 1 d D . . . .
H1D H 0.833062 0.962794 -0.003616 0.220 Uiso 1 1 calc R U . . .
H1E H 1.011931 0.967479 0.060461 0.220 Uiso 1 1 calc R U . . .
H1F H 0.827352 1.073925 0.077064 0.220 Uiso 1 1 calc R U . . .
C9 C 1.063(2) 0.463(3) 0.4468(7) 0.188(7) Uani 1 1 d . . . . .
H9A H 1.194355 0.462688 0.444395 0.282 Uiso 1 1 calc R U . . .
H9B H 1.006295 0.340524 0.419655 0.282 Uiso 1 1 calc R U . . .
H9C H 1.045341 0.457793 0.500578 0.282 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
O3 C16 1.218(14) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C2 1.502(9) . ?
C16 O2 1.226(15) . ?
C16 C13 1.4701(12) . ?
O1 C6 1.368(10) . ?
O1 C9 1.421(18) . ?
F1 C10 1.336(10) . ?
C13 C14 1.3898(12) . ?
C13 C12 1.3895(12) . ?
C4 H4 0.9300 . ?
C4 C5 1.3895(12) . ?
C4 C3 1.3896(12) . ?
C5 H5 0.9300 . ?
C5 C6 1.3898(12) . ?
C6 C7 1.3896(12) . ?
C14 H14 0.9300 . ?
C14 C15 1.3897(12) . ?
C3 C8 1.3896(12) . ?
C3 C2 1.4703(12) . ?
C7 H7 0.9300 . ?
C7 C8 1.3896(12) . ?
C8 H8 0.9300 . ?
C15 H15 0.9300 . ?
C15 C10 1.3899(12) . ?
C2 H2 0.9800 . ?
C2 C1 1.4702(12) . ?
C10 C11 1.318(15) . ?
C11 H11 0.9300 . ?
C11 C12 1.3899(12) . ?
C12 H12 0.9300 . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C1 H1F 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
O3 C16 C13 120.7(11) . . ?
O2 C16 O3 119.4(6) . . ?
O2 C16 C13 119.9(11) . . ?
C6 O1 C9 119.0(9) . . ?
C14 C13 C16 120.9(7) . . ?
C12 C13 C16 120.3(8) . . ?
C12 C13 C14 118.7(6) . . ?
C5 C4 H4 119.5 . . ?
C5 C4 C3 121.0(6) . . ?
C3 C4 H4 119.5 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(7) . . ?
C6 C5 H5 120.0 . . ?
O1 C6 C5 114.9(7) . . ?
O1 C6 C7 124.7(7) . . ?
C7 C6 C5 120.4(7) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.5(7) . . ?
C15 C14 H14 119.8 . . ?
C4 C3 C2 121.8(6) . . ?
C8 C3 C4 117.4(5) . . ?
C8 C3 C2 120.9(6) . . ?
C6 C7 H7 121.0 . . ?
C8 C7 C6 118.0(8) . . ?
C8 C7 H7 121.0 . . ?
C3 C8 C7 123.1(7) . . ?
C3 C8 H8 118.5 . . ?
C7 C8 H8 118.5 . . ?
C14 C15 H15 120.9 . . ?
C14 C15 C10 118.2(8) . . ?
C10 C15 H15 120.9 . . ?
N1 C2 H2 107.7 . . ?
C3 C2 N1 110.4(5) . . ?
C3 C2 H2 107.7 . . ?
C3 C2 C1 115.9(7) . . ?
C1 C2 N1 107.1(7) . . ?
C1 C2 H2 107.7 . . ?
F1 C10 C15 115.7(9) . . ?
C11 C10 F1 122.0(11) . . ?
C11 C10 C15 122.1(9) . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(10) . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 119.9(7) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
_geom_hbond_publ_flag
N1 H1A O3 0.89 2.24 2.983(9) 140.5 2_655 yes
N1 H1A O2 0.89 2.16 3.013(10) 160.4 2_655 yes
N1 H1B O3 0.89 1.95 2.814(11) 163.6 1_565 yes
N1 H1C O2 0.89 1.83 2.720(13) 172.3 . yes
C14 H14 O2 0.93 2.53 2.803(9) 97.3 . yes
C2 H2 O3 0.98 3.12 3.511(9) 105.5 2_655 yes
C12 H12 O3 0.93 2.53 2.798(8) 97.0 . yes
C1 H1D O2 0.96 2.69 3.491(13) 141.8 2_655 yes
C9 H9A F1 0.96 2.71 3.458(19) 134.9 1_655 yes
C9 H9C O1 0.96 2.49 3.205(16) 130.8 2_746 yes

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
O3 C16 C13 C14 170.5(8) . . . . ?
O3 C16 C13 C12 -5.6(11) . . . . ?
C16 C13 C14 C15 -175.4(7) . . . . ?
C16 C13 C12 C11 177.3(7) . . . . ?
O1 C6 C7 C8 177.4(9) . . . . ?
F1 C10 C11 C12 -179.5(8) . . . . ?
O2 C16 C13 C14 -9.0(12) . . . . ?
O2 C16 C13 C12 174.9(9) . . . . ?
C13 C14 C15 C10 0.0(12) . . . . ?
C4 C5 C6 O1 -178.3(8) . . . . ?
C4 C5 C6 C7 0.0(13) . . . . ?
C4 C3 C8 C7 2.8(12) . . . . ?
C4 C3 C2 N1 -71.0(10) . . . . ?
C4 C3 C2 C1 51.0(10) . . . . ?
C5 C4 C3 C8 -3.6(11) . . . . ?
C5 C4 C3 C2 176.3(7) . . . . ?
C5 C6 C7 C8 -0.9(13) . . . . ?
C6 C7 C8 C3 -0.6(13) . . . . ?
C14 C13 C12 C11 1.1(11) . . . . ?
C14 C15 C10 F1 -178.8(8) . . . . ?
C14 C15 C10 C11 -3.1(15) . . . . ?
C3 C4 C5 C6 2.3(12) . . . . ?
C8 C3 C2 N1 108.9(8) . . . . ?
C8 C3 C2 C1 -129.1(8) . . . . ?
C15 C10 C11 C12 5.1(16) . . . . ?
C2 C3 C8 C7 -177.1(8) . . . . ?
C10 C11 C12 C13 -4.0(14) . . . . ?
C12 C13 C14 C15 0.9(11) . . . . ?
C9 O1 C6 C5 177.5(11) . . . . ?
C9 O1 C6 C7 -0.8(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_zn-240312-h-300k_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2kfy0z
_database_code_depnum_ccdc_archive 'CCDC 2366881'
loop_
_audit_author_name
_audit_author_address
MaoWeiXin
;NanChang University
China
;
_audit_update_record             
;
2024-07-01 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;
_audit_creation_date             2024-07-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H5 O2, C9 H14 N O'
_chemical_formula_sum            'C16 H19 N O3'
_chemical_formula_weight         273.32
_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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.0189(3)
_cell_length_b                   6.0835(2)
_cell_length_c                   20.7340(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.471(3)
_cell_angle_gamma                90
_cell_volume                     1515.96(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4690
_cell_measurement_temperature    299.98(10)
_cell_measurement_theta_max      76.3130
_cell_measurement_theta_min      3.6680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8593
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.689
_diffrn_reflns_theta_min         3.678
_diffrn_ambient_temperature      299.98(10)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     39.00  65.00   0.50    0.56    --  108.36 -61.00-150.00   52
  2  ω     40.00  73.00   0.50    0.56    --  108.36 -61.00-120.00   66
  3  ω     36.00  73.00   0.50    0.56    --  108.36 -61.00 -60.00   74
  4  ω     41.00  67.00   0.50    0.56    --  108.36 -61.00 -90.00   52
  5  ω     36.00  71.00   0.50    0.56    --  108.36 -61.00  30.00   70
  6  ω     36.00 107.00   0.50    0.56    --  108.36 -77.00  90.00  142
  7  ω    -30.00  43.00   0.50    0.14    --   45.20 -37.00 120.00  146
  8  ω    107.00 154.00   0.50    0.56    --  108.36  30.00 -60.00   94
  9  ω     85.00 164.00   0.50    0.56    --  108.36  85.00  -9.00  158
 10  ω    122.00 159.00   0.50    0.56    --  108.36  30.00 -30.00   74
 11  ω     61.00 127.00   0.50    0.56    --  108.36 -85.00-129.00  132
 12  ω    -21.00  75.00   0.50    0.14    --   45.20 -85.00-129.00  192
 13  ω     -3.00  33.00   0.50    0.14    --  -45.20  19.00-180.00   72
 14  ω    -17.00  19.00   0.50    0.14    --  -45.20  19.00-120.00   72
 15  ω    -68.00 -39.00   0.50    0.56    -- -102.00  61.00-180.00   58
 16  ω    -69.00 -32.00   0.50    0.56    -- -102.00  61.00-150.00   74
 17  ω    -22.00  27.00   0.50    0.14    --  -45.20  19.00   0.00   98
 18  ω    -24.00   1.00   0.50    0.14    --  -45.20  85.00  -9.00   50
 19  ω   -104.00 -79.00   0.50    0.56    -- -102.00  85.00  -9.00   50
 20  ω   -124.00 -99.00   0.50    0.56    -- -102.00 -61.00 -90.00   50
 21  ω   -171.00-133.00   0.50    0.56    -- -102.00 -61.00 -90.00   76
 22  ω   -172.00-126.00   0.50    0.56    -- -102.00 -85.00-129.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2440
_reflns_number_total             3036
_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       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3036
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      1.050
_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)+(0.0663P)²+0.1546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1275
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14), C15(H15), C12(H12), C3(H3), C5(H5), C2(H2), C1(H1), C6(H6)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C16(H16A,H16B,H16C)
;
_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 0.60807(9) 1.16777(18) 0.69513(5) 0.0635(3) Uani 1 1 d . . . . .
O3 O 0.95589(8) 1.12162(19) 0.29840(6) 0.0721(3) Uani 1 1 d . . . . .
N1 N 0.53608(10) 0.47132(19) 0.31475(5) 0.0542(3) Uani 1 1 d . . . . .
H1A H 0.565874 0.448127 0.276193 0.065 Uiso 1 1 calc R U . . .
H1B H 0.495358 0.593476 0.313592 0.065 Uiso 1 1 calc R U . . .
H1C H 0.493026 0.357886 0.325134 0.065 Uiso 1 1 calc R U . . .
O2 O 0.59603(14) 0.8540(2) 0.64233(8) 0.1021(5) Uani 1 1 d . . . . .
C4 C 0.70815(11) 1.1286(2) 0.59763(6) 0.0508(3) Uani 1 1 d . . . . .
C10 C 0.71415(11) 0.6572(2) 0.34297(6) 0.0511(3) Uani 1 1 d . . . . .
C7 C 0.63129(11) 1.0426(2) 0.64891(7) 0.0549(3) Uani 1 1 d . . . . .
C13 C 0.88100(11) 0.9615(2) 0.31377(7) 0.0538(3) Uani 1 1 d . . . . .
C9 C 0.62662(12) 0.4956(2) 0.36398(7) 0.0561(3) Uani 1 1 d . . . . .
H9 H 0.662627 0.352042 0.369024 0.067 Uiso 1 1 calc R U . . .
C11 C 0.68880(11) 0.8573(2) 0.31386(7) 0.0570(3) Uani 1 1 d . . . . .
H11 H 0.614952 0.891540 0.304612 0.068 Uiso 1 1 calc R U . . .
C14 C 0.90840(12) 0.7626(3) 0.34195(7) 0.0616(4) Uani 1 1 d . . . . .
H14 H 0.982183 0.729551 0.351737 0.074 Uiso 1 1 calc R U . . .
C15 C 0.82501(12) 0.6130(2) 0.35545(7) 0.0601(4) Uani 1 1 d . . . . .
H15 H 0.844243 0.478169 0.373526 0.072 Uiso 1 1 calc R U . . .
C12 C 0.77070(12) 1.0054(2) 0.29852(8) 0.0582(3) Uani 1 1 d . . . . .
H12 H 0.752043 1.135923 0.277758 0.070 Uiso 1 1 calc R U . . .
C3 C 0.75767(12) 1.3322(2) 0.60361(8) 0.0626(4) Uani 1 1 d . . . . .
H3 H 0.739928 1.422383 0.638246 0.075 Uiso 1 1 calc R U . . .
C8 C 0.57469(16) 0.5548(4) 0.42794(8) 0.0789(5) Uani 1 1 d . . . . .
H8A H 0.544149 0.700417 0.425491 0.118 Uiso 1 1 calc R U . . .
H8B H 0.630438 0.549530 0.461327 0.118 Uiso 1 1 calc R U . . .
H8C H 0.516535 0.452026 0.437567 0.118 Uiso 1 1 calc R U . . .
C5 C 0.73300(16) 1.0004(3) 0.54508(8) 0.0759(5) Uani 1 1 d . . . . .
H5 H 0.698740 0.864402 0.539943 0.091 Uiso 1 1 calc R U . . .
C16 C 1.06847(13) 1.0874(4) 0.31747(10) 0.0828(5) Uani 1 1 d . . . . .
H16A H 1.097339 0.960723 0.295644 0.124 Uiso 1 1 calc R U . . .
H16B H 1.072233 1.064164 0.363228 0.124 Uiso 1 1 calc R U . . .
H16C H 1.111847 1.214214 0.306398 0.124 Uiso 1 1 calc R U . . .
C2 C 0.83369(15) 1.4027(4) 0.55827(11) 0.0866(6) Uani 1 1 d . . . . .
H2 H 0.866968 1.540004 0.562642 0.104 Uiso 1 1 calc R U . . .
C1 C 0.85994(18) 1.2720(5) 0.50730(11) 0.1034(8) Uani 1 1 d . . . . .
H1 H 0.912631 1.318136 0.477624 0.124 Uiso 1 1 calc R U . . .
C6 C 0.8086(2) 1.0724(5) 0.49977(9) 0.1045(7) Uani 1 1 d . . . . .
H6 H 0.824685 0.985207 0.464193 0.125 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
O1 C7 1.2572(17) . ?
O3 C13 1.3658(17) . ?
O3 C16 1.422(2) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C9 1.4932(19) . ?
O2 C7 1.2303(18) . ?
C4 C7 1.5079(18) . ?
C4 C3 1.379(2) . ?
C4 C5 1.374(2) . ?
C10 C9 1.5066(19) . ?
C10 C11 1.3919(19) . ?
C10 C15 1.382(2) . ?
C13 C14 1.382(2) . ?
C13 C12 1.386(2) . ?
C9 H9 0.9800 . ?
C9 C8 1.514(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.384(2) . ?
C15 H15 0.9300 . ?
C12 H12 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.385(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C5 H5 0.9300 . ?
C5 C6 1.384(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C2 H2 0.9300 . ?
C2 C1 1.362(3) . ?
C1 H1 0.9300 . ?
C1 C6 1.370(4) . ?
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
C13 O3 C16 117.27(13) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C9 N1 H1A 109.5 . . ?
C9 N1 H1B 109.5 . . ?
C9 N1 H1C 109.5 . . ?
C3 C4 C7 120.95(13) . . ?
C5 C4 C7 120.05(13) . . ?
C5 C4 C3 118.96(14) . . ?
C11 C10 C9 123.04(12) . . ?
C15 C10 C9 119.57(12) . . ?
C15 C10 C11 117.32(13) . . ?
O1 C7 C4 117.95(12) . . ?
O2 C7 O1 124.82(14) . . ?
O2 C7 C4 117.24(13) . . ?
O3 C13 C14 124.60(13) . . ?
O3 C13 C12 116.12(12) . . ?
C14 C13 C12 119.27(13) . . ?
N1 C9 C10 111.94(11) . . ?
N1 C9 H9 107.7 . . ?
N1 C9 C8 108.60(13) . . ?
C10 C9 H9 107.7 . . ?
C10 C9 C8 113.09(12) . . ?
C8 C9 H9 107.7 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.28(13) . . ?
C12 C11 H11 119.4 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.39(13) . . ?
C15 C14 H14 120.3 . . ?
C10 C15 C14 122.21(13) . . ?
C10 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C13 C12 H12 119.8 . . ?
C11 C12 C13 120.46(13) . . ?
C11 C12 H12 119.8 . . ?
C4 C3 H3 119.9 . . ?
C4 C3 C2 120.26(17) . . ?
C2 C3 H3 119.9 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.46(19) . . ?
C6 C5 H5 119.8 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C3 C2 H2 119.9 . . ?
C1 C2 C3 120.3(2) . . ?
C1 C2 H2 119.9 . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C6 119.95(18) . . ?
C6 C1 H1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 C5 120.0(2) . . ?
C1 C6 H6 120.0 . . ?

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
_geom_hbond_publ_flag
N1 H1A O1 0.89 1.90 2.7662(14) 165.5 4_575 yes
N1 H1B O1 0.89 1.92 2.8033(16) 171.9 3_676 yes
N1 H1C O2 0.89 1.81 2.6931(16) 171.6 3_666 yes
C11 H11 O1 0.93 2.70 3.5746(17) 156.0 3_676 yes
C11 H11 N1 0.93 2.74 2.9807(18) 96.1 . yes
C14 H14 O3 0.93 3.27 3.456(2) 93.4 2_745 yes
C15 H15 O3 0.93 2.99 3.5831(19) 122.7 1_545 yes
C12 H12 O1 0.93 2.70 3.5073(18) 145.2 4_585 yes
C3 H3 O1 0.93 2.52 2.8088(18) 98.5 . yes
C8 H8C O2 0.96 2.83 3.531(2) 130.7 3_666 yes
C5 H5 O2 0.93 2.47 2.761(2) 98.5 . yes

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
O3 C13 C14 C15 179.87(14) . . . . ?
O3 C13 C12 C11 -178.01(13) . . . . ?
C4 C3 C2 C1 0.2(3) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C10 C11 C12 C13 -2.2(2) . . . . ?
C7 C4 C3 C2 175.74(14) . . . . ?
C7 C4 C5 C6 -176.07(17) . . . . ?
C13 C14 C15 C10 -1.4(2) . . . . ?
C9 C10 C11 C12 176.47(13) . . . . ?
C9 C10 C15 C14 -174.78(14) . . . . ?
C11 C10 C9 N1 42.94(18) . . . . ?
C11 C10 C9 C8 -80.11(18) . . . . ?
C11 C10 C15 C14 2.2(2) . . . . ?
C14 C13 C12 C11 3.0(2) . . . . ?
C15 C10 C9 N1 -140.30(13) . . . . ?
C15 C10 C9 C8 96.65(17) . . . . ?
C15 C10 C11 C12 -0.4(2) . . . . ?
C12 C13 C14 C15 -1.2(2) . . . . ?
C3 C4 C7 O1 4.5(2) . . . . ?
C3 C4 C7 O2 -175.34(16) . . . . ?
C3 C4 C5 C6 1.6(3) . . . . ?
C3 C2 C1 C6 1.9(3) . . . . ?
C5 C4 C7 O1 -177.84(14) . . . . ?
C5 C4 C7 O2 2.3(2) . . . . ?
C5 C4 C3 C2 -1.9(2) . . . . ?
C16 O3 C13 C14 -5.2(2) . . . . ?
C16 O3 C13 C12 175.83(15) . . . . ?
C2 C1 C6 C5 -2.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_zn_240222-4-r-300k_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2kfxxv
_database_code_depnum_ccdc_archive 'CCDC 2366878'
loop_
_audit_author_name
_audit_author_address
MaoWeiXin
;NanChang University
China
;
_audit_update_record             
;
2024-07-01 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;
_audit_creation_date             2024-07-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H14 N O, C7 H5 O2'
_chemical_formula_sum            'C16 H19 N O3'
_chemical_formula_weight         273.32
_chemical_absolute_configuration syn
_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'
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      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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.1092(2)
_cell_length_b                   7.3483(3)
_cell_length_c                   33.6266(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1509.57(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3000
_cell_measurement_temperature    299.98(11)
_cell_measurement_theta_max      74.6180
_cell_measurement_theta_min      2.6190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            6934
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.321
_diffrn_reflns_theta_min         2.628
_diffrn_ambient_temperature      300.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     49.00  74.00   0.50    1.10    --  108.36 -94.00-180.00   50
  2  ω     56.00 110.00   0.50    1.10    --  108.36-125.00 -90.00  108
  3  ω     56.00 102.00   0.50    1.10    --  108.36 -94.00  60.00   92
  4  ω     44.00  71.00   0.50    1.10    --  108.36 -61.00   0.00   54
  5  ω     37.00  72.00   0.50    1.10    --  108.36 -61.00 -90.00   70
  6  ω    -31.00  19.00   0.50    0.28    --   45.45 -20.00  -4.00  100
  7  ω     93.00 176.00   0.50    1.10    --  108.36  20.00 162.00  166
  8  ω     88.00 113.00   0.50    0.28    --   45.45 152.00  33.00   50
  9  ω    -14.00  31.00   0.50    0.28    --  -45.45  20.00 162.00   90
 10  ω    -31.00  28.00   0.50    0.28    --  -45.45  37.00-120.00  118
 11  ω    -62.00 -33.00   0.50    1.10    -- -102.00  77.00-180.00   58
 12  ω    -69.00 -30.00   0.50    1.10    -- -102.00  61.00-180.00   78
 13  ω   -104.00 -74.00   0.50    1.10    -- -102.00  77.00-180.00   60
 14  ω    -68.00 -42.00   0.50    1.10    -- -102.00  61.00 -90.00   52
 15  ω   -106.00 -76.00   0.50    1.10    -- -102.00 106.00 -26.00   60
 16  ω    -86.00 -28.00   0.50    1.10    -- -102.00 152.00  33.00  116
 17  ω    -72.00 -32.00   0.50    1.10    -- -102.00 106.00 -26.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.651
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                2459
_reflns_number_total             3002
_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       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 816 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.22(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3002
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.054
_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)+(0.0785P)²+0.0678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1413
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C3(H3), C7(H7), C16(H16), C12(H12), C15(H15), C13(H13),
 C14(H14)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C1(H1D,H1E,H1F)
;
_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 0.5627(4) 0.5607(4) 0.71033(6) 0.0952(7) Uani 1 1 d . . . . .
O3 O -0.0993(4) 0.0631(3) 0.55254(6) 0.0930(7) Uani 1 1 d . . . . .
N1 N 0.6160(4) 0.3427(3) 0.53051(5) 0.0696(6) Uani 1 1 d . . . . .
H1A H 0.615999 0.335660 0.504088 0.083 Uiso 1 1 calc R U . . .
H1B H 0.487668 0.304305 0.539830 0.083 Uiso 1 1 calc R U . . .
H1C H 0.722597 0.273213 0.540237 0.083 Uiso 1 1 calc R U . . .
O2 O 0.2166(4) 0.1942(4) 0.55166(6) 0.1098(9) Uani 1 1 d . . . . .
C10 C 0.0703(5) 0.1112(4) 0.56938(8) 0.0709(6) Uani 1 1 d . . . . .
C11 C 0.0934(4) 0.0804(3) 0.61366(7) 0.0628(6) Uani 1 1 d . . . . .
C2 C 0.5744(5) 0.5652(4) 0.66962(7) 0.0698(6) Uani 1 1 d . . . . .
C5 C 0.6289(4) 0.5519(3) 0.58755(7) 0.0645(6) Uani 1 1 d . . . . .
C6 C 0.4459(5) 0.6307(4) 0.60439(8) 0.0721(7) Uani 1 1 d . . . . .
H6 H 0.338531 0.678876 0.587847 0.086 Uiso 1 1 calc R U . . .
C4 C 0.7882(5) 0.4839(4) 0.61308(8) 0.0728(7) Uani 1 1 d . . . . .
H4 H 0.915294 0.433927 0.602474 0.087 Uiso 1 1 calc R U . . .
C3 C 0.7620(5) 0.4888(4) 0.65330(8) 0.0760(7) Uani 1 1 d . . . . .
H3 H 0.869636 0.440941 0.669825 0.091 Uiso 1 1 calc R U . . .
C7 C 0.4177(5) 0.6400(4) 0.64517(8) 0.0764(7) Uani 1 1 d . . . . .
H7 H 0.294557 0.695964 0.655900 0.092 Uiso 1 1 calc R U . . .
C8 C 0.6524(5) 0.5366(4) 0.54295(8) 0.0744(7) Uani 1 1 d . . . . .
H8 H 0.537535 0.610995 0.530742 0.089 Uiso 1 1 calc R U . . .
C16 C -0.0691(5) -0.0087(4) 0.63408(8) 0.0733(7) Uani 1 1 d . . . . .
H16 H -0.186558 -0.058546 0.620269 0.088 Uiso 1 1 calc R U . . .
C12 C 0.2690(5) 0.1502(5) 0.63432(9) 0.0806(8) Uani 1 1 d . . . . .
H12 H 0.382412 0.207010 0.620676 0.097 Uiso 1 1 calc R U . . .
C15 C -0.0594(6) -0.0250(5) 0.67493(9) 0.0914(9) Uani 1 1 d . . . . .
H15 H -0.169467 -0.085997 0.688626 0.110 Uiso 1 1 calc R U . . .
C13 C 0.2770(7) 0.1363(5) 0.67503(10) 0.0970(10) Uani 1 1 d . . . . .
H13 H 0.394364 0.186266 0.688843 0.116 Uiso 1 1 calc R U . . .
C9 C 0.8694(7) 0.5996(6) 0.52669(10) 0.1063(12) Uani 1 1 d . . . . .
H9A H 0.983900 0.522568 0.536631 0.160 Uiso 1 1 calc R U . . .
H9B H 0.895821 0.722791 0.534914 0.160 Uiso 1 1 calc R U . . .
H9C H 0.866695 0.593682 0.498179 0.160 Uiso 1 1 calc R U . . .
C14 C 0.1147(7) 0.0500(5) 0.69529(9) 0.0997(11) Uani 1 1 d . . . . .
H14 H 0.121120 0.041466 0.722862 0.120 Uiso 1 1 calc R U . . .
C1 C 0.3627(7) 0.6134(8) 0.72795(10) 0.1193(15) Uani 1 1 d . . . . .
H1D H 0.246531 0.538788 0.717747 0.179 Uiso 1 1 calc R U . . .
H1E H 0.333499 0.738631 0.721825 0.179 Uiso 1 1 calc R U . . .
H1F H 0.372067 0.598442 0.756261 0.179 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
O1 C2 1.371(3) . ?
O1 C1 1.412(4) . ?
O3 C10 1.233(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C8 1.501(4) . ?
O2 C10 1.235(4) . ?
C10 C11 1.513(3) . ?
C11 C16 1.373(4) . ?
C11 C12 1.377(4) . ?
C2 C3 1.390(4) . ?
C2 C7 1.376(4) . ?
C5 C6 1.381(4) . ?
C5 C4 1.390(4) . ?
C5 C8 1.511(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.384(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.362(4) . ?
C3 H3 0.9300 . ?
C7 H7 0.9300 . ?
C8 H8 0.9800 . ?
C8 C9 1.507(5) . ?
C16 H16 0.9300 . ?
C16 C15 1.380(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.373(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.380(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.360(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C14 H14 0.9300 . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C1 H1F 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
C2 O1 C1 117.2(2) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C8 N1 H1A 109.5 . . ?
C8 N1 H1B 109.5 . . ?
C8 N1 H1C 109.5 . . ?
O3 C10 O2 121.9(3) . . ?
O3 C10 C11 119.2(3) . . ?
O2 C10 C11 118.8(2) . . ?
C16 C11 C10 119.7(2) . . ?
C16 C11 C12 119.2(2) . . ?
C12 C11 C10 120.9(2) . . ?
O1 C2 C3 115.3(2) . . ?
O1 C2 C7 124.7(3) . . ?
C7 C2 C3 119.9(2) . . ?
C6 C5 C4 117.7(2) . . ?
C6 C5 C8 121.0(2) . . ?
C4 C5 C8 121.3(2) . . ?
C5 C6 H6 119.1 . . ?
C5 C6 C7 121.9(2) . . ?
C7 C6 H6 119.1 . . ?
C5 C4 H4 119.3 . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 H4 119.3 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C7 C6 119.1(3) . . ?
C2 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
N1 C8 C5 109.5(2) . . ?
N1 C8 H8 107.8 . . ?
N1 C8 C9 108.7(3) . . ?
C5 C8 H8 107.8 . . ?
C9 C8 C5 114.9(3) . . ?
C9 C8 H8 107.8 . . ?
C11 C16 H16 119.7 . . ?
C11 C16 C15 120.5(3) . . ?
C15 C16 H16 119.7 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C16 C15 H15 120.3 . . ?
C16 C15 C14 119.5(3) . . ?
C14 C15 H15 120.3 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 119.7 . . ?
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 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
O1 C1 H1D 109.5 . . ?
O1 C1 H1E 109.5 . . ?
O1 C1 H1F 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?

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
_geom_hbond_publ_flag
N1 H1A O3 0.89 2.43 3.163(3) 139.8 4_556 yes
N1 H1A O2 0.89 1.98 2.844(3) 161.7 4_556 yes
N1 H1B O2 0.89 1.89 2.766(3) 169.7 . yes
N1 H1C O3 0.89 1.93 2.792(3) 161.6 1_655 yes
C16 H16 O3 0.93 2.50 2.798(3) 98.6 . yes
C12 H12 O2 0.93 2.53 2.817(4) 97.9 . yes
C9 H9B O3 0.96 2.57 3.520(5) 170.3 1_665 yes
C9 H9C O2 0.96 2.85 3.532(4) 128.8 4_556 yes

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 C2 C3 C4 179.0(3) . . . . ?
O1 C2 C7 C6 -178.0(3) . . . . ?
O3 C10 C11 C16 3.4(4) . . . . ?
O3 C10 C11 C12 -172.6(3) . . . . ?
O2 C10 C11 C16 178.8(3) . . . . ?
O2 C10 C11 C12 2.9(4) . . . . ?
C10 C11 C16 C15 -174.7(3) . . . . ?
C10 C11 C12 C13 173.7(3) . . . . ?
C11 C16 C15 C14 0.3(5) . . . . ?
C11 C12 C13 C14 1.5(6) . . . . ?
C5 C6 C7 C2 -1.4(5) . . . . ?
C5 C4 C3 C2 -0.9(4) . . . . ?
C6 C5 C4 C3 2.2(4) . . . . ?
C6 C5 C8 N1 -105.8(3) . . . . ?
C6 C5 C8 C9 131.5(3) . . . . ?
C4 C5 C6 C7 -1.1(4) . . . . ?
C4 C5 C8 N1 72.8(3) . . . . ?
C4 C5 C8 C9 -49.9(4) . . . . ?
C3 C2 C7 C6 2.7(4) . . . . ?
C7 C2 C3 C4 -1.6(4) . . . . ?
C8 C5 C6 C7 177.6(3) . . . . ?
C8 C5 C4 C3 -176.5(3) . . . . ?
C16 C11 C12 C13 -2.3(5) . . . . ?
C16 C15 C14 C13 -1.1(5) . . . . ?
C12 C11 C16 C15 1.4(4) . . . . ?
C12 C13 C14 C15 0.2(6) . . . . ?
C1 O1 C2 C3 -171.4(3) . . . . ?
C1 O1 C2 C7 9.3(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_zn-240222-1r-340k--2_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2kfy10
_database_code_depnum_ccdc_archive 'CCDC 2366882'
loop_
_audit_author_name
_audit_author_address
MaoWeiXin
;NanChang University
China
;
_audit_update_record             
;
2024-07-01 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;
_audit_creation_date             2024-07-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H14 N O, C7 H4 F O2'
_chemical_formula_sum            'C16 H18 F N O3'
_chemical_formula_weight         291.31
_chemical_absolute_configuration syn
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.2750(8)
_cell_length_b                   6.2945(7)
_cell_length_c                   17.3045(18)
_cell_angle_alpha                90
_cell_angle_beta                 99.161(10)
_cell_angle_gamma                90
_cell_volume                     782.31(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1292
_cell_measurement_temperature    339.99(12)
_cell_measurement_theta_max      67.5200
_cell_measurement_theta_min      2.6080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3984
_diffrn_reflns_point_group_measured_fraction_full 0.827
_diffrn_reflns_point_group_measured_fraction_max 0.758
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.923
_diffrn_reflns_theta_min         2.586
_diffrn_ambient_temperature      339.99(12)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  30.00   0.50    0.50    --  -44.83  19.00-180.00  108
  2  ω    -10.00  19.00   0.50    0.50    --  -44.83  19.00-120.00   58
  3  ω    -62.00 -29.00   0.50    1.20    -- -102.00  61.00 -30.00   66
  4  ω    -68.00 -41.00   0.50    1.20    -- -102.00  61.00 -60.00   54
  5  ω    -24.00   2.00   0.50    0.50    --  -44.83  19.00   0.00   52
  6  ω    -46.00 -19.00   0.50    0.50    --  -44.83 105.00 159.00   54
  7  ω   -101.00 -43.00   0.50    1.20    -- -102.00 105.00 159.00  116
  8  ω   -141.00 -85.00   0.50    1.20    -- -102.00-105.00  60.00  112
  9  ω      3.00  81.00   0.50    0.50    --   44.83-105.00  60.00  156
 10  ω     48.00  73.00   0.50    1.20    --  108.36-105.00  60.00   50
 11  ω     36.00  76.00   0.50    1.20    --  108.36 -94.00  60.00   80
 12  ω     77.00 105.00   0.50    1.20    --  108.36 -94.00  60.00   56
 13  ω     43.00  70.00   0.50    1.20    --  108.36 -61.00  90.00   54
 14  ω     39.00  66.00   0.50    1.20    --  108.36 -61.00 120.00   54
 15  ω     36.00  68.00   0.50    1.20    --  108.36 -61.00  60.00   64
 16  ω     37.00  70.00   0.50    1.20    --  108.36 -61.00  30.00   66
 17  ω     36.00  72.00   0.50    1.20    --  108.36 -61.00 -30.00   72
 18  ω    -28.00  44.00   0.50    0.50    --   44.83 -37.00 -60.00  144
 19  ω     35.00  73.00   0.50    1.20    --  108.36 -61.00-180.00   76
 20  ω     92.00 177.00   0.50    1.20    --  108.36  15.00 -90.00  170
 21  ω    138.00 171.00   0.50    1.20    --  108.36  61.00 120.00   66
 22  ω     90.00 136.00   0.50    1.20    --  108.36  61.00 120.00   92
 23  ω    117.00 143.00   0.50    1.20    --  108.36 105.00 159.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.519
_reflns_Friedel_fraction_full    0.649
_reflns_Friedel_fraction_max     0.573
_reflns_number_gt                1664
_reflns_number_total             2504
_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       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 
;
 Flack x determined using 484 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2504
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0764
_refine_ls_restrained_S_all      1.038
_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)+(0.1570P)²+0.0173P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2153
_refine_ls_wR_factor_ref         0.2433
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C16(H16), C7(H7), C12(H12), C3(H3), C15(H15), C4(H4), C13(H13)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C1(H1D,H1E,H1F)
;
_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
N1 N 0.6160(6) 0.2561(8) 0.0593(2) 0.0817(11) Uani 1 1 d . . . . .
H1A H 0.589454 0.262929 0.007381 0.098 Uiso 1 1 calc R U . . .
H1B H 0.576756 0.373942 0.079985 0.098 Uiso 1 1 calc R U . . .
H1C H 0.559399 0.144005 0.076270 0.098 Uiso 1 1 calc R U . . .
O3 O 0.3769(7) 0.9449(10) 0.1002(3) 0.1191(17) Uani 1 1 d . . . . .
O1 O 0.9826(8) 0.3390(10) 0.4102(3) 0.136(2) Uani 1 1 d . . . . .
C11 C 0.4283(6) 0.7926(8) 0.2259(3) 0.0734(12) Uani 1 1 d . . . . .
F1 F 0.4682(9) 0.8282(16) 0.4635(3) 0.192(4) Uani 1 1 d . . . . .
C10 C 0.4231(7) 0.7809(10) 0.1400(3) 0.0847(14) Uani 1 1 d . . . . .
C5 C 0.8712(6) 0.2630(10) 0.1700(3) 0.0795(13) Uani 1 1 d . . . . .
O2 O 0.4704(10) 0.6233(13) 0.1094(3) 0.167(3) Uani 1 1 d . . . . .
C6 C 0.8283(8) 0.1128(10) 0.2219(3) 0.0920(17) Uani 1 1 d . . . . .
H6 H 0.771155 -0.012437 0.202243 0.110 Uiso 1 1 calc R U . . .
C16 C 0.5054(8) 0.6264(11) 0.2740(4) 0.0946(17) Uani 1 1 d . . . . .
H16 H 0.546296 0.504781 0.251412 0.114 Uiso 1 1 calc R U . . .
C2 C 0.9537(8) 0.3263(11) 0.3307(3) 0.0947(18) Uani 1 1 d . . . . .
C8 C 0.8218(7) 0.2350(11) 0.0835(3) 0.0882(15) Uani 1 1 d . . . . .
H8 H 0.881419 0.349972 0.058337 0.106 Uiso 1 1 calc R U . . .
C7 C 0.8658(8) 0.1396(11) 0.3002(4) 0.0988(18) Uani 1 1 d . . . . .
H7 H 0.833565 0.035075 0.333626 0.119 Uiso 1 1 calc R U . . .
C12 C 0.3613(8) 0.9670(11) 0.2602(4) 0.0939(16) Uani 1 1 d . . . . .
H12 H 0.307200 1.078267 0.229327 0.113 Uiso 1 1 calc R U . . .
C3 C 1.0042(8) 0.4729(11) 0.2806(4) 0.0978(18) Uani 1 1 d . . . . .
H3 H 1.067308 0.594753 0.300163 0.117 Uiso 1 1 calc R U . . .
C15 C 0.5217(10) 0.6388(16) 0.3534(4) 0.116(2) Uani 1 1 d . . . . .
H15 H 0.577823 0.529780 0.385008 0.139 Uiso 1 1 calc R U . . .
C4 C 0.9633(8) 0.4429(11) 0.2016(4) 0.0940(17) Uani 1 1 d . . . . .
H4 H 0.998068 0.545928 0.168179 0.113 Uiso 1 1 calc R U . . .
C14 C 0.4546(11) 0.8134(18) 0.3856(4) 0.118(3) Uani 1 1 d . . . . .
C13 C 0.3744(10) 0.9771(16) 0.3411(5) 0.120(3) Uani 1 1 d . . . . .
H13 H 0.328826 1.094591 0.364576 0.144 Uiso 1 1 calc R U . . .
C9 C 0.8821(12) 0.027(2) 0.0518(5) 0.151(4) Uani 1 1 d . . . . .
H9A H 0.819056 -0.088134 0.072837 0.226 Uiso 1 1 calc R U . . .
H9B H 1.014162 0.010331 0.066744 0.226 Uiso 1 1 calc R U . . .
H9C H 0.851443 0.026807 -0.004232 0.226 Uiso 1 1 calc R U . . .
C1 C 1.063(2) 0.531(3) 0.4452(6) 0.195(6) Uani 1 1 d . . . . .
H1D H 0.978826 0.646931 0.430547 0.293 Uiso 1 1 calc R U . . .
H1E H 1.178689 0.557795 0.427351 0.293 Uiso 1 1 calc R U . . .
H1F H 1.083703 0.515847 0.501119 0.293 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
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C8 1.495(7) . ?
O3 C10 1.256(8) . ?
O1 C2 1.361(7) . ?
O1 C1 1.431(15) . ?
C11 C10 1.482(7) . ?
C11 C16 1.398(8) . ?
C11 C12 1.374(8) . ?
F1 C14 1.341(8) . ?
C10 O2 1.200(9) . ?
C5 C6 1.373(8) . ?
C5 C8 1.495(7) . ?
C5 C4 1.383(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.350(8) . ?
C16 H16 0.9300 . ?
C16 C15 1.362(9) . ?
C2 C7 1.400(9) . ?
C2 C3 1.357(9) . ?
C8 H8 0.9800 . ?
C8 C9 1.511(12) . ?
C7 H7 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.388(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.365(8) . ?
C15 H15 0.9300 . ?
C15 C14 1.357(14) . ?
C4 H4 0.9300 . ?
C14 C13 1.361(13) . ?
C13 H13 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C1 H1F 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
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C8 N1 H1A 109.5 . . ?
C8 N1 H1B 109.5 . . ?
C8 N1 H1C 109.5 . . ?
C2 O1 C1 117.6(7) . . ?
C16 C11 C10 120.3(5) . . ?
C12 C11 C10 121.3(5) . . ?
C12 C11 C16 118.4(5) . . ?
O3 C10 C11 118.1(6) . . ?
O2 C10 O3 120.5(6) . . ?
O2 C10 C11 121.3(6) . . ?
C6 C5 C8 122.0(6) . . ?
C6 C5 C4 116.9(5) . . ?
C4 C5 C8 121.1(5) . . ?
C5 C6 H6 118.7 . . ?
C7 C6 C5 122.6(6) . . ?
C7 C6 H6 118.7 . . ?
C11 C16 H16 119.3 . . ?
C15 C16 C11 121.4(6) . . ?
C15 C16 H16 119.3 . . ?
O1 C2 C7 114.7(6) . . ?
C3 C2 O1 126.4(6) . . ?
C3 C2 C7 118.9(5) . . ?
N1 C8 H8 107.7 . . ?
N1 C8 C9 108.1(6) . . ?
C5 C8 N1 109.9(4) . . ?
C5 C8 H8 107.7 . . ?
C5 C8 C9 115.4(6) . . ?
C9 C8 H8 107.7 . . ?
C6 C7 C2 119.4(6) . . ?
C6 C7 H7 120.3 . . ?
C2 C7 H7 120.3 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.1(7) . . ?
C13 C12 H12 120.0 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(6) . . ?
C4 C3 H3 119.7 . . ?
C16 C15 H15 120.7 . . ?
C14 C15 C16 118.7(7) . . ?
C14 C15 H15 120.7 . . ?
C5 C4 H4 119.2 . . ?
C3 C4 C5 121.5(5) . . ?
C3 C4 H4 119.2 . . ?
F1 C14 C15 119.7(9) . . ?
F1 C14 C13 118.2(9) . . ?
C15 C14 C13 122.1(6) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.3(7) . . ?
C14 C13 H13 120.3 . . ?
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 . . ?
O1 C1 H1D 109.5 . . ?
O1 C1 H1E 109.5 . . ?
O1 C1 H1F 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?

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
_geom_hbond_publ_flag
N1 H1A O3 0.89 2.23 3.013(7) 146.3 2_645 yes
N1 H1A O2 0.89 2.18 3.006(7) 153.5 2_645 yes
N1 H1B O2 0.89 1.86 2.740(7) 171.6 . yes
N1 H1C O3 0.89 1.92 2.785(7) 164.1 1_545 yes
C16 H16 O2 0.93 2.54 2.820(8) 97.5 . yes
C8 H8 O3 0.98 3.13 3.531(7) 106.5 2_645 yes
C12 H12 O3 0.93 2.51 2.793(8) 97.6 . yes
C9 H9C O2 0.96 2.79 3.529(11) 133.9 2_645 yes
C1 H1E F1 0.96 2.70 3.467(16) 137.0 1_655 yes
C1 H1F O1 0.96 2.64 3.224(13) 119.8 2_756 yes

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 C2 C7 C6 179.1(6) . . . . ?
O1 C2 C3 C4 -178.6(7) . . . . ?
C11 C16 C15 C14 2.6(9) . . . . ?
C11 C12 C13 C14 0.3(10) . . . . ?
F1 C14 C13 C12 179.0(6) . . . . ?
C10 C11 C16 C15 176.1(5) . . . . ?
C10 C11 C12 C13 -177.6(5) . . . . ?
C5 C6 C7 C2 -0.7(10) . . . . ?
C6 C5 C8 N1 71.1(7) . . . . ?
C6 C5 C8 C9 -51.4(8) . . . . ?
C6 C5 C4 C3 -2.0(8) . . . . ?
C16 C11 C10 O3 -170.2(5) . . . . ?
C16 C11 C10 O2 6.0(8) . . . . ?
C16 C11 C12 C13 1.3(8) . . . . ?
C16 C15 C14 F1 179.5(6) . . . . ?
C16 C15 C14 C13 -1.0(11) . . . . ?
C2 C3 C4 C5 -0.6(9) . . . . ?
C8 C5 C6 C7 -177.4(6) . . . . ?
C8 C5 C4 C3 178.1(5) . . . . ?
C7 C2 C3 C4 2.7(9) . . . . ?
C12 C11 C10 O3 8.6(7) . . . . ?
C12 C11 C10 O2 -175.2(7) . . . . ?
C12 C11 C16 C15 -2.8(8) . . . . ?
C3 C2 C7 C6 -2.0(10) . . . . ?
C15 C14 C13 C12 -0.4(12) . . . . ?
C4 C5 C6 C7 2.7(8) . . . . ?
C4 C5 C8 N1 -109.0(5) . . . . ?
C4 C5 C8 C9 128.5(7) . . . . ?
C1 O1 C2 C7 -176.6(9) . . . . ?
C1 O1 C2 C3 4.6(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_zn-240312-f_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2kfxzx
_database_code_depnum_ccdc_archive 'CCDC 2366880'
loop_
_audit_author_name
_audit_author_address
MaoWeiXin
;NanChang University
China
;
_audit_update_record             
;
2024-07-01 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;
_audit_creation_date             2024-07-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H4 F O2, C9 H14 N O'
_chemical_formula_sum            'C16 H18 F N O3'
_chemical_formula_weight         291.31
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.2351(3)
_cell_length_b                   6.07500(10)
_cell_length_c                   20.6390(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.293(2)
_cell_angle_gamma                90
_cell_volume                     1533.67(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5457
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      76.3930
_cell_measurement_theta_min      3.5890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9684
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.520
_diffrn_reflns_theta_min         3.613
_diffrn_ambient_temperature      300(2)
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  20.00   0.50    0.24    --   45.45 -15.00-100.00   50
  2  ω     36.00  70.00   0.50    0.98    --  108.36 -61.00  60.00   68
  3  ω     35.00  69.00   0.50    0.98    --  108.36 -61.00  90.00   68
  4  ω     22.00 123.00   0.50    0.24    --   45.45  15.00  70.00  202
  5  ω    104.00 178.00   0.50    0.98    --  108.36  30.00 150.00  148
  6  ω     85.00 134.00   0.50    0.98    --  108.36  15.00  70.00   98
  7  ω    107.00 137.00   0.50    0.98    --  108.36  61.00 -30.00   60
  8  ω    152.00 178.00   0.50    0.98    --  108.36  61.00 -30.00   52
  9  ω     72.00  97.00   0.50    0.98    --  108.36 -94.00-120.00   50
 10  ω     78.00 109.00   0.50    0.98    --  108.36-125.00-180.00   62
 11  ω     35.00  61.00   0.50    0.98    --  108.36 -94.00-120.00   52
 12  ω     30.00  92.00   0.50    0.24    --   45.45-125.00-150.00  124
 13  ω   -166.00 -79.00   0.50    0.98    -- -102.00 -15.00-100.00  174
 14  ω   -119.00 -21.00   0.50    0.24    --  -45.45 -15.00-100.00  196
 15  ω    -63.00 -38.00   0.50    0.98    -- -102.00 125.00  60.00   50
 16  ω   -111.00 -69.00   0.50    0.98    -- -102.00 125.00  60.00   84
 17  ω    -22.00   3.00   0.50    0.24    --  -45.45  15.00  70.00   50
 18  ω    -69.00 -44.00   0.50    0.98    -- -102.00  61.00  30.00   50
 19  ω   -103.00 -76.00   0.50    0.98    -- -102.00  77.00-150.00   54
 20  ω    -68.00 -30.00   0.50    0.98    -- -102.00  61.00-150.00   76
 21  ω    -66.00 -35.00   0.50    0.98    -- -102.00  61.00-180.00   62
 22  ω    -16.00  10.00   0.50    0.24    --  -45.45  19.00-180.00   52
 23  ω    -64.00 -34.00   0.50    0.98    -- -102.00  77.00-150.00   60
 24  ω    -69.00 -31.00   0.50    0.98    -- -102.00  61.00-120.00   76
 25  ω    -54.00 -28.00   0.50    0.98    -- -102.00  61.00  90.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2523
_reflns_number_total             3067
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.0035(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3067
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.067
_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)+(0.0518P)²+0.1867P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1130
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C13(H13), C5(H5), C4(H4), C8(H8), C12(H12), C15(H15), C10(H10)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C1(H1D,H1E,H1F)
;
_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
O2 O 0.39318(8) -0.16791(17) 0.30541(5) 0.0613(3) Uani 1 1 d . . . . .
O3 O 0.04947(8) -0.12247(19) 0.70308(6) 0.0681(3) Uani 1 1 d . . . . .
F1 F 0.06242(9) -0.2848(2) 0.53262(6) 0.1071(4) Uani 1 1 d . . . . .
N1 N 0.46189(9) 0.52463(18) 0.68569(5) 0.0523(3) Uani 1 1 d . . . . .
H1A H 0.504130 0.638124 0.675442 0.063 Uiso 1 1 calc R U . . .
H1B H 0.501756 0.402092 0.686810 0.063 Uiso 1 1 calc R U . . .
H1C H 0.433400 0.547593 0.724410 0.063 Uiso 1 1 calc R U . . .
O1 O 0.41109(13) 0.1485(2) 0.35712(7) 0.0988(5) Uani 1 1 d . . . . .
C14 C 0.29397(10) -0.1132(2) 0.40131(6) 0.0476(3) Uani 1 1 d . . . . .
C6 C 0.12298(11) 0.0359(2) 0.68690(6) 0.0517(3) Uani 1 1 d . . . . .
C3 C 0.28627(11) 0.3390(2) 0.65694(6) 0.0498(3) Uani 1 1 d . . . . .
C16 C 0.37220(11) -0.0376(2) 0.35086(7) 0.0538(3) Uani 1 1 d . . . . .
C2 C 0.37184(12) 0.5013(2) 0.63599(7) 0.0558(3) Uani 1 1 d . . . . .
H2 H 0.336429 0.645148 0.630967 0.067 Uiso 1 1 calc R U . . .
C7 C 0.23137(11) -0.0084(2) 0.70227(7) 0.0566(3) Uani 1 1 d . . . . .
H7 H 0.250041 -0.138870 0.723319 0.068 Uiso 1 1 calc R U . . .
C13 C 0.24202(11) -0.3148(2) 0.39673(7) 0.0560(3) Uani 1 1 d . . . . .
H13 H 0.259151 -0.411062 0.363433 0.067 Uiso 1 1 calc R U . . .
C5 C 0.09577(12) 0.2347(3) 0.65790(7) 0.0589(4) Uani 1 1 d . . . . .
H5 H 0.023123 0.267758 0.647865 0.071 Uiso 1 1 calc R U . . .
C4 C 0.17740(12) 0.3836(2) 0.64399(7) 0.0577(3) Uani 1 1 d . . . . .
H4 H 0.158339 0.518004 0.625331 0.069 Uiso 1 1 calc R U . . .
C8 C 0.31175(11) 0.1395(2) 0.68657(7) 0.0568(3) Uani 1 1 d . . . . .
H8 H 0.384485 0.105372 0.695982 0.068 Uiso 1 1 calc R U . . .
C12 C 0.16427(13) -0.3745(3) 0.44161(9) 0.0680(4) Uani 1 1 d . . . . .
H12 H 0.128984 -0.509890 0.438749 0.082 Uiso 1 1 calc R U . . .
C15 C 0.26939(14) 0.0251(3) 0.45226(8) 0.0662(4) Uani 1 1 d . . . . .
H15 H 0.305231 0.159552 0.456349 0.079 Uiso 1 1 calc R U . . .
C11 C 0.14104(13) -0.2300(3) 0.48986(8) 0.0705(5) Uani 1 1 d . . . . .
C9 C -0.06083(13) -0.0924(4) 0.68206(9) 0.0775(5) Uani 1 1 d . . . . .
H9A H -0.063783 -0.072771 0.635898 0.116 Uiso 1 1 calc R U . . .
H9B H -0.090345 0.035509 0.702669 0.116 Uiso 1 1 calc R U . . .
H9C H -0.102929 -0.219432 0.693406 0.116 Uiso 1 1 calc R U . . .
C1 C 0.42249(16) 0.4424(4) 0.57167(7) 0.0812(5) Uani 1 1 d . . . . .
H1D H 0.479901 0.544814 0.562549 0.122 Uiso 1 1 calc R U . . .
H1E H 0.367526 0.449140 0.537791 0.122 Uiso 1 1 calc R U . . .
H1F H 0.452036 0.296184 0.574048 0.122 Uiso 1 1 calc R U . . .
C10 C 0.19241(16) -0.0334(3) 0.49719(8) 0.0791(5) Uani 1 1 d . . . . .
H10 H 0.176294 0.059505 0.531487 0.095 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
O2 C16 1.2582(17) . ?
O3 C6 1.3638(17) . ?
O3 C9 1.4200(19) . ?
F1 C11 1.3613(17) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C2 1.4951(18) . ?
O1 C16 1.2326(18) . ?
C14 C16 1.5020(17) . ?
C14 C13 1.3818(19) . ?
C14 C15 1.385(2) . ?
C6 C7 1.3830(19) . ?
C6 C5 1.385(2) . ?
C3 C2 1.5084(19) . ?
C3 C4 1.380(2) . ?
C3 C8 1.3896(19) . ?
C2 H2 0.9800 . ?
C2 C1 1.520(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.376(2) . ?
C13 H13 0.9300 . ?
C13 C12 1.391(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.383(2) . ?
C4 H4 0.9300 . ?
C8 H8 0.9300 . ?
C12 H12 0.9300 . ?
C12 C11 1.362(3) . ?
C15 H15 0.9300 . ?
C15 C10 1.383(2) . ?
C11 C10 1.357(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C1 H1F 0.9600 . ?
C10 H10 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
C6 O3 C9 117.50(12) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
C13 C14 C16 121.53(12) . . ?
C13 C14 C15 118.83(13) . . ?
C15 C14 C16 119.59(12) . . ?
O3 C6 C7 116.16(12) . . ?
O3 C6 C5 124.58(12) . . ?
C7 C6 C5 119.26(13) . . ?
C4 C3 C2 119.30(12) . . ?
C4 C3 C8 117.57(13) . . ?
C8 C3 C2 123.08(12) . . ?
O2 C16 C14 117.93(12) . . ?
O1 C16 O2 124.79(13) . . ?
O1 C16 C14 117.28(13) . . ?
N1 C2 C3 111.78(11) . . ?
N1 C2 H2 107.8 . . ?
N1 C2 C1 108.23(12) . . ?
C3 C2 H2 107.8 . . ?
C3 C2 C1 113.31(12) . . ?
C1 C2 H2 107.8 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.37(13) . . ?
C8 C7 H7 119.8 . . ?
C14 C13 H13 119.8 . . ?
C14 C13 C12 120.41(14) . . ?
C12 C13 H13 119.8 . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.51(13) . . ?
C4 C5 H5 120.2 . . ?
C3 C4 C5 122.00(13) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C3 C8 H8 119.4 . . ?
C7 C8 C3 121.23(13) . . ?
C7 C8 H8 119.4 . . ?
C13 C12 H12 120.8 . . ?
C11 C12 C13 118.41(15) . . ?
C11 C12 H12 120.8 . . ?
C14 C15 H15 119.5 . . ?
C10 C15 C14 121.08(15) . . ?
C10 C15 H15 119.5 . . ?
F1 C11 C12 118.60(17) . . ?
C10 C11 F1 118.37(17) . . ?
C10 C11 C12 123.03(14) . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
C15 C10 H10 120.9 . . ?
C11 C10 C15 118.19(15) . . ?
C11 C10 H10 120.9 . . ?

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
_geom_hbond_publ_flag
N1 H1A O1 0.89 1.80 2.6834(15) 171.6 3_666 yes
N1 H1B O2 0.89 1.92 2.8035(16) 170.6 3_656 yes
N1 H1C O2 0.89 1.90 2.7682(14) 164.8 4_566 yes
C7 H7 O2 0.93 2.68 3.4825(18) 145.0 4_556 yes
C13 H13 O2 0.93 2.53 2.8153(16) 98.2 . yes
C5 H5 O3 0.93 3.29 3.5176(19) 96.4 2_556 yes
C4 H4 F1 0.93 2.52 3.3428(18) 147.0 1_565 yes
C8 H8 N1 0.93 2.73 2.9748(18) 96.2 . yes
C12 H12 F1 0.93 2.73 3.511(2) 142.1 3_546 yes
C15 H15 O1 0.93 2.45 2.7527(19) 99.1 . yes
C1 H1D O1 0.96 2.81 3.514(2) 130.8 3_666 yes

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
O3 C6 C7 C8 178.59(13) . . . . ?
O3 C6 C5 C4 179.66(13) . . . . ?
F1 C11 C10 C15 -177.68(16) . . . . ?
C14 C13 C12 C11 -0.1(2) . . . . ?
C14 C15 C10 C11 -0.3(3) . . . . ?
C6 C7 C8 C3 2.0(2) . . . . ?
C6 C5 C4 C3 1.3(2) . . . . ?
C16 C14 C13 C12 -175.52(13) . . . . ?
C16 C14 C15 C10 175.75(15) . . . . ?
C2 C3 C4 C5 175.44(13) . . . . ?
C2 C3 C8 C7 -177.00(13) . . . . ?
C7 C6 C5 C4 0.9(2) . . . . ?
C13 C14 C16 O2 -3.2(2) . . . . ?
C13 C14 C16 O1 176.76(15) . . . . ?
C13 C14 C15 C10 -1.6(2) . . . . ?
C13 C12 C11 F1 177.86(14) . . . . ?
C13 C12 C11 C10 -1.9(3) . . . . ?
C5 C6 C7 C8 -2.6(2) . . . . ?
C4 C3 C2 N1 140.63(13) . . . . ?
C4 C3 C2 C1 -96.75(17) . . . . ?
C4 C3 C8 C7 0.2(2) . . . . ?
C8 C3 C2 N1 -42.22(18) . . . . ?
C8 C3 C2 C1 80.39(18) . . . . ?
C8 C3 C4 C5 -1.9(2) . . . . ?
C12 C11 C10 C15 2.1(3) . . . . ?
C15 C14 C16 O2 179.61(14) . . . . ?
C15 C14 C16 O1 -0.5(2) . . . . ?
C15 C14 C13 C12 1.7(2) . . . . ?
C9 O3 C6 C7 -173.68(14) . . . . ?
C9 O3 C6 C5 7.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
