# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_0320-6chenjing_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2db89b
_database_code_depnum_ccdc_archive 'CCDC 2214401'
loop_
_audit_author_name
_audit_author_address
'Xi Chen'
;Tianjin Institute of Industrial Biotechnology Chinese Academy of Sciences
China
;
_audit_update_record             
;
2025-02-13 deposited with the CCDC.	2025-06-25 downloaded from the CCDC.
;
_audit_creation_date             2024-03-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        0320-6
_chemical_formula_moiety         'C16 H23 N O3'
_chemical_formula_sum            'C16 H23 N O3'
_chemical_formula_weight         277.35
_chemical_absolute_configuration ?
_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           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                   5.7962(3)
_cell_length_b                   9.4231(4)
_cell_length_c                   13.7625(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.430(5)
_cell_angle_gamma                90
_cell_volume                     736.79(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11291
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.5110
_cell_measurement_theta_min      3.1870
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.934
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14295
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.542
_diffrn_reflns_theta_min         3.276
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     61.00 107.00   0.50    0.10    --   54.36  30.00 -30.00   92
  2  ω     85.00 131.00   0.50    0.10    --   78.20  30.00-180.00   92
  3  ω     61.00 107.00   0.50    0.10    --   54.36  30.00-120.00   92
  4  ω     85.00 131.00   0.50    0.10    --   78.20  30.00 -90.00   92
  5  ω     92.00 138.00   0.50    0.10    --   85.54  30.00   0.00   92
  6  ω     61.00 107.00   0.50    0.10    --   54.36  30.00   0.00   92
  7  ω     61.00  93.00   0.50    0.10    --   54.36  30.00  30.00   64
  8  ω     72.00 118.00   0.50    0.10    --   65.53  30.00  90.00   92
  9  ω     92.00 138.00   0.50    0.10    --   85.54  30.00 120.00   92
 10  ω     48.00 133.00   0.50    0.10    --   85.54  15.00  90.00  170
 11  ω     29.00  97.00   0.50    0.10    --   78.20-111.00 150.00  136
 12  ω     22.00  74.00   0.50    0.10    --   65.53 -95.00 150.00  104
 13  ω     29.00  97.00   0.50    0.10    --   78.20-111.00 120.00  136
 14  ω     42.00  93.00   0.50    0.10    --   85.54 -95.00  30.00  102
 15  ω     42.00  93.00   0.50    0.10    --   85.54 -95.00 -90.00  102
 16  ω     42.00  93.00   0.50    0.10    --   85.54 -95.00-135.00  102
 17  ω     42.00  93.00   0.50    0.10    --   85.54 -95.00-180.00  102
 18  ω     11.00  62.00   0.50    0.10    --   54.36 -95.00-135.00  102
 19  ω     22.00  74.00   0.50    0.10    --   65.53 -95.00-135.00  104
 20  ω     35.00  86.00   0.50    0.10    --   78.20 -95.00-135.00  102
 21  ω     11.00  62.00   0.50    0.10    --   54.36 -95.00 -60.00  102
 22  ω     11.00  62.00   0.50    0.10    --   54.36 -95.00 120.00  102
 23  ω     11.00  62.00   0.50    0.10    --   54.36 -95.00  90.00  102
 24  ω    -85.00 -34.00   0.50    0.10    --  -77.27  95.00 -25.00  102
 25  ω    -96.00 -33.00   0.50    0.10    --  -82.00 111.00-120.00  126
 26  ω    -97.00 -28.00   0.50    0.10    --  -77.27 111.00 -90.00  138
 27  ω    -97.00 -28.00   0.50    0.10    --  -77.27 111.00-150.00  138
 28  ω    -97.00 -28.00   0.50    0.10    --  -77.27 111.00 -60.00  138
 29  ω    -90.00 -38.00   0.50    0.10    --  -82.00  95.00 -25.00  104
 30  ω    -66.00 -14.00   0.50    0.10    --  -57.83  95.00 -25.00  104
 31  ω    -77.00 -25.00   0.50    0.10    --  -69.06  95.00 -25.00  104
 32  ω    -96.00 -33.00   0.50    0.10    --  -82.00 111.00   0.00  126
 33  ω    -98.00 -20.00   0.50    0.10    --  -69.06 125.00   0.00  156
 34  ω    -97.00 -28.00   0.50    0.10    --  -77.27 111.00 120.00  138
 35  ω   -109.00 -38.00   0.50    0.10    --  -57.83 -15.00 -90.00  142
 36  ω   -130.00 -85.00   0.50    0.10    --  -77.27 -30.00-120.00   90
 37  ω   -130.00 -85.00   0.50    0.10    --  -77.27 -30.00 -90.00   90
 38  ω   -134.00 -89.00   0.50    0.10    --  -82.00 -30.00-150.00   90
 39  ω   -134.00 -89.00   0.50    0.10    --  -82.00 -30.00 -60.00   90
 40  ω   -130.00 -85.00   0.50    0.10    --  -77.27 -30.00   0.00   90
 41  ω   -110.00 -65.00   0.50    0.10    --  -57.83 -30.00  30.00   90
 42  ω   -130.00 -85.00   0.50    0.10    --  -77.27 -30.00 -30.00   90
 43  ω   -130.00 -85.00   0.50    0.10    --  -77.27 -30.00  90.00   90
 44  ω   -130.00 -85.00   0.50    0.10    --  -77.27 -30.00 120.00   90
 45  ω   -130.00 -85.00   0.50    0.10    --  -77.27 -30.00 150.00   90
 46  ω   -110.00 -65.00   0.50    0.10    --  -57.83 -30.00 120.00   90
 47  ω   -110.00 -65.00   0.50    0.10    --  -57.83 -30.00  60.00   90
 48  ω   -134.00 -89.00   0.50    0.10    --  -82.00 -30.00  60.00   90
 49  ω   -134.00 -89.00   0.50    0.10    --  -82.00 -30.00  30.00   90
 50  ω   -110.00 -65.00   0.50    0.10    --  -57.83 -30.00-150.00   90
 51  ω   -130.00 -85.00   0.50    0.10    --  -77.27 -30.00-180.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0620357000
_diffrn_orient_matrix_UB_12      0.0261818000
_diffrn_orient_matrix_UB_13      0.1023310000
_diffrn_orient_matrix_UB_21      -0.1062352000
_diffrn_orient_matrix_UB_22      -0.1500995000
_diffrn_orient_matrix_UB_23      -0.0022029000
_diffrn_orient_matrix_UB_31      0.2415441000
_diffrn_orient_matrix_UB_32      -0.0592998000
_diffrn_orient_matrix_UB_33      0.0507355000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_full    0.952
_reflns_Friedel_fraction_max     0.872
_reflns_number_gt                2639
_reflns_number_total             2747
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 1126 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(17)
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2747
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.133
_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)+(0.0729P)²+0.0061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1054
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1(H1A,H1B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C8(H8), C12(H12), C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O20(H20)
;
_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
O19 O 0.1011(3) 0.59615(18) 0.57147(11) 0.0236(4) Uani 1 1 d . . . . .
O14 O 0.2965(3) 0.56981(17) 0.73138(11) 0.0229(4) Uani 1 1 d . . . . .
C2 C 0.4314(4) 0.9762(3) 0.55770(16) 0.0217(5) Uani 1 1 d . . . . .
H2A H 0.290552 1.016887 0.577828 0.026 Uiso 1 1 calc R U . . .
H2B H 0.446009 1.020060 0.493819 0.026 Uiso 1 1 calc R U . . .
C11 C 1.2268(4) 0.9471(3) 0.91412(17) 0.0261(5) Uani 1 1 d . . . . .
H11 H 1.374759 0.900294 0.924294 0.031 Uiso 1 1 calc R U . . .
N6 N 0.4007(3) 0.7453(2) 0.63869(14) 0.0218(4) Uani 1 1 d . . . . .
O20 O 0.8616(3) 0.96578(19) 0.60846(11) 0.0242(4) Uani 1 1 d . . . . .
H20 H 0.872820 1.002570 0.553992 0.036 Uiso 1 1 calc R U . . .
C4 C 0.6298(4) 0.9384(2) 0.73349(15) 0.0198(5) Uani 1 1 d . . . . .
H4 H 0.480522 0.972068 0.751875 0.024 Uiso 1 1 calc R U . . .
C15 C 0.1888(4) 0.4309(2) 0.74556(16) 0.0207(5) Uani 1 1 d . . . . .
C1 C 0.3986(4) 0.8169(2) 0.54353(16) 0.0233(5) Uani 1 1 d . . . . .
H1A H 0.246997 0.797899 0.497850 0.028 Uiso 1 1 calc R U . . .
H1B H 0.526413 0.778176 0.513129 0.028 Uiso 1 1 calc R U . . .
C8 C 0.7948(4) 1.0823(3) 0.88543(17) 0.0235(5) Uani 1 1 d . . . . .
H8 H 0.646845 1.129056 0.876128 0.028 Uiso 1 1 calc R U . . .
C12 C 1.0501(4) 0.9092(3) 0.83407(16) 0.0239(5) Uani 1 1 d . . . . .
H12 H 1.079095 0.837573 0.789412 0.029 Uiso 1 1 calc R U . . .
C5 C 0.6062(4) 0.7774(2) 0.71695(16) 0.0218(5) Uani 1 1 d . . . . .
H5A H 0.750407 0.740135 0.697714 0.026 Uiso 1 1 calc R U . . .
H5B H 0.588510 0.730384 0.779373 0.026 Uiso 1 1 calc R U . . .
C16 C 0.3099(4) 0.3926(3) 0.85083(17) 0.0267(5) Uani 1 1 d . . . . .
H16A H 0.276424 0.465777 0.896704 0.040 Uiso 1 1 calc R U . . .
H16B H 0.480236 0.386556 0.854549 0.040 Uiso 1 1 calc R U . . .
H16C H 0.251058 0.300826 0.868971 0.040 Uiso 1 1 calc R U . . .
C18 C -0.0755(4) 0.4463(3) 0.73899(18) 0.0265(5) Uani 1 1 d . . . . .
H18A H -0.149833 0.476967 0.672055 0.040 Uiso 1 1 calc R U . . .
H18B H -0.105041 0.517094 0.787260 0.040 Uiso 1 1 calc R U . . .
H18C H -0.141675 0.354808 0.753447 0.040 Uiso 1 1 calc R U . . .
C13 C 0.2555(4) 0.6336(2) 0.64144(16) 0.0207(5) Uani 1 1 d . . . . .
C9 C 0.9713(4) 1.1210(3) 0.96474(18) 0.0286(5) Uani 1 1 d . . . . .
H9 H 0.943757 1.193704 1.008866 0.034 Uiso 1 1 calc R U . . .
C3 C 0.6497(4) 1.0125(2) 0.63608(16) 0.0197(5) Uani 1 1 d . . . . .
H3 H 0.657106 1.117538 0.646741 0.024 Uiso 1 1 calc R U . . .
C10 C 1.1872(4) 1.0535(3) 0.97934(17) 0.0276(5) Uani 1 1 d . . . . .
H10 H 1.308168 1.079507 1.033630 0.033 Uiso 1 1 calc R U . . .
C7 C 0.8298(4) 0.9761(2) 0.81904(15) 0.0197(5) Uani 1 1 d . . . . .
C17 C 0.2459(4) 0.3217(3) 0.67235(18) 0.0275(5) Uani 1 1 d . . . . .
H17A H 0.415366 0.322656 0.673327 0.041 Uiso 1 1 calc R U . . .
H17B H 0.159777 0.344838 0.605535 0.041 Uiso 1 1 calc R U . . .
H17C H 0.199182 0.227132 0.691053 0.041 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
O19 C13 1.229(3) . ?
O14 C15 1.480(3) . ?
O14 C13 1.354(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.521(3) . ?
C2 C3 1.530(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.394(3) . ?
C11 C10 1.395(4) . ?
N6 C1 1.471(3) . ?
N6 C5 1.470(3) . ?
N6 C13 1.354(3) . ?
O20 H20 0.8400 . ?
O20 C3 1.426(3) . ?
C4 H4 1.0000 . ?
C4 C5 1.536(3) . ?
C4 C3 1.536(3) . ?
C4 C7 1.521(3) . ?
C15 C16 1.523(3) . ?
C15 C18 1.523(3) . ?
C15 C17 1.522(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C8 H8 0.9500 . ?
C8 C9 1.389(3) . ?
C8 C7 1.397(3) . ?
C12 H12 0.9500 . ?
C12 C7 1.402(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C9 H9 0.9500 . ?
C9 C10 1.382(4) . ?
C3 H3 1.0000 . ?
C10 H10 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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 O14 C15 120.72(17) . . ?
H2A C2 H2B 107.9 . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C1 C2 C3 112.1(2) . . ?
C3 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C12 C11 H11 119.9 . . ?
C12 C11 C10 120.3(2) . . ?
C10 C11 H11 119.9 . . ?
C5 N6 C1 114.88(18) . . ?
C13 N6 C1 119.07(18) . . ?
C13 N6 C5 123.90(18) . . ?
C3 O20 H20 109.5 . . ?
C5 C4 H4 107.1 . . ?
C5 C4 C3 109.86(18) . . ?
C3 C4 H4 107.1 . . ?
C7 C4 H4 107.1 . . ?
C7 C4 C5 112.14(18) . . ?
C7 C4 C3 113.07(18) . . ?
O14 C15 C16 102.00(17) . . ?
O14 C15 C18 110.70(19) . . ?
O14 C15 C17 110.99(18) . . ?
C16 C15 C18 110.35(19) . . ?
C17 C15 C16 110.5(2) . . ?
C17 C15 C18 111.9(2) . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
N6 C1 C2 111.07(18) . . ?
N6 C1 H1A 109.4 . . ?
N6 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C9 C8 H8 119.3 . . ?
C9 C8 C7 121.5(2) . . ?
C7 C8 H8 119.3 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C7 120.4(2) . . ?
C7 C12 H12 119.8 . . ?
N6 C5 C4 110.31(18) . . ?
N6 C5 H5A 109.6 . . ?
N6 C5 H5B 109.6 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O19 C13 O14 123.9(2) . . ?
O19 C13 N6 124.2(2) . . ?
N6 C13 O14 111.92(18) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 H9 120.1 . . ?
C2 C3 C4 108.61(18) . . ?
C2 C3 H3 109.3 . . ?
O20 C3 C2 112.25(17) . . ?
O20 C3 C4 108.04(17) . . ?
O20 C3 H3 109.3 . . ?
C4 C3 H3 109.3 . . ?
C11 C10 H10 120.1 . . ?
C9 C10 C11 119.8(2) . . ?
C9 C10 H10 120.1 . . ?
C8 C7 C4 119.10(19) . . ?
C8 C7 C12 118.1(2) . . ?
C12 C7 C4 122.8(2) . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C12 C7 C4 -179.5(2) . . . . ?
C11 C12 C7 C8 0.9(3) . . . . ?
C15 O14 C13 O19 12.7(3) . . . . ?
C15 O14 C13 N6 -168.82(18) . . . . ?
C1 C2 C3 O20 63.0(2) . . . . ?
C1 C2 C3 C4 -56.4(2) . . . . ?
C1 N6 C5 C4 55.5(3) . . . . ?
C1 N6 C13 O19 -8.4(3) . . . . ?
C1 N6 C13 O14 173.14(19) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C12 C11 C10 C9 0.3(4) . . . . ?
C5 N6 C1 C2 -52.9(3) . . . . ?
C5 N6 C13 O19 -170.8(2) . . . . ?
C5 N6 C13 O14 10.7(3) . . . . ?
C5 C4 C3 C2 58.1(2) . . . . ?
C5 C4 C3 O20 -63.9(2) . . . . ?
C5 C4 C7 C8 -138.0(2) . . . . ?
C5 C4 C7 C12 42.5(3) . . . . ?
C13 O14 C15 C16 172.18(19) . . . . ?
C13 O14 C15 C18 -70.4(2) . . . . ?
C13 O14 C15 C17 54.5(3) . . . . ?
C13 N6 C1 C2 143.1(2) . . . . ?
C13 N6 C5 C4 -141.4(2) . . . . ?
C9 C8 C7 C4 -179.9(2) . . . . ?
C9 C8 C7 C12 -0.4(3) . . . . ?
C3 C2 C1 N6 53.0(3) . . . . ?
C3 C4 C5 N6 -57.5(2) . . . . ?
C3 C4 C7 C8 97.2(2) . . . . ?
C3 C4 C7 C12 -82.4(3) . . . . ?
C10 C11 C12 C7 -0.9(3) . . . . ?
C7 C4 C5 N6 175.84(17) . . . . ?
C7 C4 C3 C2 -175.77(18) . . . . ?
C7 C4 C3 O20 62.2(2) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?

_olex2_submission_original_sample_id 0320-6
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.067
_oxdiff_exptl_absorpt_empirical_full_min 0.603
####################################################################### 
# 
# 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_15shang
_audit_block_doi                 10.5517/ccdc.csd.cc2mnr13
_database_code_depnum_ccdc_archive 'CCDC 2433005'
loop_
_audit_author_name
_audit_author_address
'Xi Chen'
;Tianjin Institute of Industrial Biotechnology Chinese Academy of Sciences
China
;
_audit_update_record             
;
2025-03-21 deposited with the CCDC.	2025-06-25 downloaded from the CCDC.
;
_audit_creation_date             2025-02-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_chemical_name_systematic        1
_chemical_formula_moiety         'C16 H22 F N O3'
_chemical_formula_sum            'C16 H22 F N O3'
_chemical_formula_weight         295.356
_chemical_absolute_configuration ad
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01788 0.00908 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
F 0.07327 0.05351 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.03110 0.01806 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03234 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   5.5276(2)
_cell_length_b                   22.2991(8)
_cell_length_c                   12.7260(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1568.61(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10473
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      73.9460
_cell_measurement_theta_min      3.8710
_exptl_absorpt_coefficient_mu    0.774
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       block
_exptl_crystal_F_000             634.290
_exptl_crystal_preparation       'single crystal'
_exptl_crystal_recrystallization_method 'vapor diffusion'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.9964
_diffrn_reflns_Laue_measured_fraction_max 0.9727
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16020
_diffrn_reflns_point_group_measured_fraction_full 0.9772
_diffrn_reflns_point_group_measured_fraction_max 0.9356
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         74.23
_diffrn_reflns_theta_min         3.96
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      103(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.9727
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -92.00 -31.00   0.50    0.05    --  -77.31 111.00 120.00  122
  2  ω    -92.00 -67.00   0.50    0.05    --  -77.31 111.00  90.00   50
  3  ω    -92.00 -31.00   0.50    0.05    --  -77.31 111.00 -60.00  122
  4  ω    -80.00 -24.00   0.50    0.05    --  -68.04 100.00-153.00  112
  5  ω    -89.00 -33.00   0.50    0.05    --  -77.31 100.00-153.00  112
  6  ω    -69.00 -13.00   0.50    0.05    --  -57.13 100.00-153.00  112
  7  ω   -109.00 -38.00   0.50    0.05    --  -57.13 -15.00-120.00  142
  8  ω   -130.00 -85.00   0.50    0.05    --  -77.31 -30.00-180.00   90
  9  ω   -130.00 -85.00   0.50    0.05    --  -77.31 -30.00-120.00   90
 10  ω   -130.00 -85.00   0.50    0.05    --  -77.31 -30.00  60.00   90
 11  ω     85.00 131.00   0.50    0.05    --   78.29  30.00 150.00   92
 12  ω     92.00 138.00   0.50    0.05    --   85.54  30.00 120.00   92
 13  ω     60.00 106.00   0.50    0.05    --   53.69  30.00 120.00   92
 14  ω     71.00 117.00   0.50    0.05    --   64.60  30.00  60.00   92
 15  ω     92.00 138.00   0.50    0.05    --   85.54  30.00   0.00   92
 16  ω     85.00 131.00   0.50    0.05    --   78.29  30.00  30.00   92
 17  ω     85.00 131.00   0.50    0.05    --   78.29  30.00 -30.00   92
 18  ω     85.00 131.00   0.50    0.05    --   78.29  30.00 -60.00   92
 19  ω     71.00 117.00   0.50    0.05    --   64.60  30.00 -90.00   92
 20  ω     92.00 138.00   0.50    0.05    --   85.54  30.00-150.00   92
 21  ω     92.00 138.00   0.50    0.05    --   85.54  30.00-180.00   92
 22  ω     92.00 138.00   0.50    0.05    --   85.54  30.00  90.00   92
 23  ω      9.00  65.00   0.50    0.05    --   53.69-100.00 101.00  112
 24  ω     20.00  76.00   0.50    0.05    --   64.60-100.00 101.00  112
 25  ω     34.00  90.00   0.50    0.05    --   78.29-100.00 101.00  112
 26  ω     41.00  92.00   0.50    0.05    --   85.54-100.00 101.00  102
 27  ω     35.00  86.00   0.50    0.05    --   78.29 -95.00  30.00  102
 28  ω     42.00  92.00   0.50    0.05    --   85.54 -95.00   0.00  100
 29  ω     21.00  73.00   0.50    0.05    --   64.60 -95.00 -30.00  104
 30  ω     35.00  86.00   0.50    0.05    --   78.29 -95.00 -90.00  102
 31  ω     42.00  92.00   0.50    0.05    --   85.54 -95.00-180.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2386456000
_diffrn_orient_matrix_UB_12      -0.0354438000
_diffrn_orient_matrix_UB_13      0.0069801000
_diffrn_orient_matrix_UB_21      0.1148854000
_diffrn_orient_matrix_UB_22      -0.0421692000
_diffrn_orient_matrix_UB_23      0.0818901000
_diffrn_orient_matrix_UB_31      -0.0867064000
_diffrn_orient_matrix_UB_32      0.0416970000
_diffrn_orient_matrix_UB_33      0.0888847000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.883
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              26
_reflns_limit_k_min              -26
_reflns_limit_l_max              15
_reflns_limit_l_min              -15
_reflns_number_gt                2593
_reflns_number_total             2978
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.4476
_refine_diff_density_min         -0.4465
_refine_diff_density_rms         0.0955
_refine_ls_abs_structure_details 
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.14(9)
_refine_ls_d_res_high            0.8011
_refine_ls_d_res_low             11.1496
_refine_ls_goodness_of_fit_ref   1.0474
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2978
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0655
_refine_ls_restrained_S_all      1.0474
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²+1.1509P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1707
_refine_ls_wR_factor_ref         0.1783
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C007(H007), C008(H008)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00b,H00c), C00E(H00e,H00f), C00F(H00g,H00h)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00D(H00D), C00H(H00i), C00I(H00j)
2.d Idealised Me refined as rotating group:
 C00J(H00k,H00l,H00m), C00K(H00n,H00o,H00p), C00L(H00q,H00r,H00s)
2.e Idealised tetrahedral OH refined as rotating group:
 O004(H004)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O001 O -0.6429(4) -0.64003(10) -0.57590(17) 0.0333(5) Uani 1.000000 .
F002 F -0.2256(5) -0.70690(11) 0.04953(18) 0.0550(6) Uani 1.000000 .
O003 O -0.6671(4) -0.54893(10) -0.65545(19) 0.0382(5) Uani 1.000000 .
O004 O -0.0712(5) -0.51314(11) -0.3121(2) 0.0406(6) Uani 1.000000 .
H004 H -0.0052(6) -0.4927(17) -0.265(2) 0.0609(9) Uiso 1.000000 GR
N005 N -0.4628(6) -0.56123(12) -0.5017(2) 0.0358(6) Uani 1.000000 .
C006 C -0.5982(5) -0.58120(15) -0.5829(2) 0.0309(7) Uani 1.000000 .
C007 C -0.3271(6) -0.50652(15) -0.3056(3) 0.0347(7) Uani 1.000000 .
H007 H -0.3704(6) -0.48616(15) -0.2381(3) 0.0416(9) Uiso 1.000000 R
C008 C -0.4448(6) -0.56861(14) -0.3091(2) 0.0318(7) Uani 1.000000 .
H008 H -0.6239(6) -0.56238(14) -0.3079(2) 0.0381(8) Uiso 1.000000 R
C009 C -0.3816(6) -0.60657(14) -0.2149(2) 0.0316(7) Uani 1.000000 .
C00A C -0.1678(6) -0.63907(15) -0.2078(3) 0.0360(7) Uani 1.000000 .
H00A H -0.0550(6) -0.63774(15) -0.2641(3) 0.0432(9) Uiso 1.000000 R
C00B C -0.3831(6) -0.59857(14) -0.4139(2) 0.0348(7) Uani 1.000000 .
H00b H -0.4632(6) -0.63821(14) -0.4178(2) 0.0417(9) Uiso 1.000000 R
H00c H -0.2062(6) -0.60496(14) -0.4185(2) 0.0417(9) Uiso 1.000000 R
C00C C -0.2775(7) -0.67367(16) -0.0376(3) 0.0397(8) Uani 1.000000 .
C00D C -0.5400(7) -0.60805(17) -0.1297(3) 0.0397(8) Uani 1.000000 .
H00D H -0.6852(7) -0.58533(17) -0.1327(3) 0.0477(9) Uiso 1.000000 R
C00E C -0.4191(7) -0.46914(14) -0.3983(3) 0.0384(8) Uani 1.000000 .
H00e H -0.5957(7) -0.46297(14) -0.3912(3) 0.0461(10) Uiso 1.000000 R
H00f H -0.3400(7) -0.42930(14) -0.3974(3) 0.0461(10) Uiso 1.000000 R
C00F C -0.3660(7) -0.50007(15) -0.5022(3) 0.0373(8) Uani 1.000000 .
H00g H -0.1890(7) -0.50134(15) -0.5139(3) 0.0448(9) Uiso 1.000000 R
H00h H -0.4401(7) -0.47703(15) -0.5603(3) 0.0448(9) Uiso 1.000000 R
C00G C -0.7951(6) -0.67115(15) -0.6542(3) 0.0331(7) Uani 1.000000 .
C00H C -0.1168(7) -0.67354(16) -0.1194(3) 0.0403(8) Uani 1.000000 .
H00i H 0.0274(7) -0.69663(16) -0.1159(3) 0.0484(10) Uiso 1.000000 R
C00I C -0.4906(7) -0.64197(18) -0.0405(3) 0.0453(9) Uani 1.000000 .
H00j H -0.6009(7) -0.64318(18) 0.0167(3) 0.0544(11) Uiso 1.000000 R
C00J C -0.7794(7) -0.73576(16) -0.6195(3) 0.0425(9) Uani 1.000000 .
H00k H -0.6108(11) -0.7492(4) -0.623(2) 0.0638(13) Uiso 1.000000 GR
H00l H -0.838(5) -0.7393(3) -0.5472(9) 0.0638(13) Uiso 1.000000 GR
H00m H -0.879(4) -0.7607(2) -0.6660(15) 0.0638(13) Uiso 1.000000 GR
C00K C -0.6920(7) -0.66449(18) -0.7650(3) 0.0426(8) Uani 1.000000 .
H00n H -0.704(5) -0.6225(3) -0.7872(9) 0.0639(13) Uiso 1.000000 GR
H00o H -0.5219(15) -0.6769(12) -0.7653(5) 0.0639(13) Uiso 1.000000 GR
H00p H -0.784(3) -0.6898(10) -0.8137(5) 0.0639(13) Uiso 1.000000 GR
C00L C -1.0517(7) -0.64858(18) -0.6480(3) 0.0449(9) Uani 1.000000 .
H00q H -1.1180(18) -0.6571(11) -0.5782(8) 0.0673(13) Uiso 1.000000 GR
H00r H -1.0540(9) -0.6052(3) -0.660(2) 0.0673(13) Uiso 1.000000 GR
H00s H -1.1501(13) -0.6687(9) -0.7015(15) 0.0673(13) Uiso 1.000000 GR


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
O001 C006 1.338(4) . ?
O001 C00G 1.477(4) . ?
F002 C00C 1.364(4) . ?
O003 C006 1.231(4) . ?
O004 H004 0.8400 . ?
O004 C007 1.425(4) . ?
N005 C006 1.352(4) . ?
N005 C00B 1.461(4) . ?
N005 C00F 1.465(4) . ?
C007 H007 1.0000 . ?
C007 C008 1.530(5) . ?
C007 C00E 1.532(5) . ?
C008 H008 1.0000 . ?
C008 C009 1.509(4) . ?
C008 C00B 1.530(4) . ?
C009 C00A 1.389(5) . ?
C009 C00D 1.393(5) . ?
C00A H00A 0.9500 . ?
C00A C00H 1.392(5) . ?
C00B H00b 0.9900 . ?
C00B H00c 0.9900 . ?
C00C C00H 1.368(5) . ?
C00C C00I 1.375(6) . ?
C00D H00D 0.9500 . ?
C00D C00I 1.391(5) . ?
C00E H00e 0.9900 . ?
C00E H00f 0.9900 . ?
C00E C00F 1.519(5) . ?
C00F H00g 0.9900 . ?
C00F H00h 0.9900 . ?
C00G C00J 1.509(5) . ?
C00G C00K 1.529(5) . ?
C00G C00L 1.507(5) . ?
C00H H00i 0.9500 . ?
C00I H00j 0.9500 . ?
C00J H00k 0.9800 . ?
C00J H00l 0.9800 . ?
C00J H00m 0.9800 . ?
C00K H00n 0.9800 . ?
C00K H00o 0.9800 . ?
C00K H00p 0.9800 . ?
C00L H00q 0.9800 . ?
C00L H00r 0.9800 . ?
C00L H00s 0.9800 . ?

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
C00G O001 C006 121.4(2) . . ?
C007 O004 H004 109.5 . . ?
C00B N005 C006 124.3(3) . . ?
C00F N005 C006 120.4(3) . . ?
C00F N005 C00B 115.1(3) . . ?
O003 C006 O001 124.5(3) . . ?
N005 C006 O001 112.0(3) . . ?
N005 C006 O003 123.5(3) . . ?
H007 C007 O004 109.56(17) . . ?
C008 C007 O004 109.1(3) . . ?
C008 C007 H007 109.56(17) . . ?
C00E C007 O004 109.9(3) . . ?
C00E C007 H007 109.56(17) . . ?
C00E C007 C008 109.2(3) . . ?
H008 C008 C007 107.14(18) . . ?
C009 C008 C007 112.7(3) . . ?
C009 C008 H008 107.14(18) . . ?
C00B C008 C007 109.1(3) . . ?
C00B C008 H008 107.14(18) . . ?
C00B C008 C009 113.3(3) . . ?
C00A C009 C008 122.7(3) . . ?
C00D C009 C008 119.1(3) . . ?
C00D C009 C00A 118.1(3) . . ?
H00A C00A C009 119.57(19) . . ?
C00H C00A C009 120.9(3) . . ?
C00H C00A H00A 119.6(2) . . ?
C008 C00B N005 110.5(3) . . ?
H00b C00B N005 109.55(17) . . ?
H00b C00B C008 109.55(17) . . ?
H00c C00B N005 109.55(19) . . ?
H00c C00B C008 109.55(18) . . ?
H00c C00B H00b 108.1 . . ?
C00H C00C F002 118.9(3) . . ?
C00I C00C F002 118.8(3) . . ?
C00I C00C C00H 122.3(3) . . ?
H00D C00D C009 119.2(2) . . ?
C00I C00D C009 121.6(3) . . ?
C00I C00D H00D 119.2(2) . . ?
H00e C00E C007 109.43(19) . . ?
H00f C00E C007 109.43(18) . . ?
H00f C00E H00e 108.0 . . ?
C00F C00E C007 111.0(3) . . ?
C00F C00E H00e 109.4(2) . . ?
C00F C00E H00f 109.43(18) . . ?
C00E C00F N005 110.4(3) . . ?
H00g C00F N005 109.6(2) . . ?
H00g C00F C00E 109.6(2) . . ?
H00h C00F N005 109.58(19) . . ?
H00h C00F C00E 109.58(19) . . ?
H00h C00F H00g 108.1 . . ?
C00J C00G O001 102.6(3) . . ?
C00K C00G O001 111.4(3) . . ?
C00K C00G C00J 109.9(3) . . ?
C00L C00G O001 110.1(3) . . ?
C00L C00G C00J 111.0(3) . . ?
C00L C00G C00K 111.5(3) . . ?
C00C C00H C00A 119.0(3) . . ?
H00i C00H C00A 120.5(2) . . ?
H00i C00H C00C 120.5(2) . . ?
C00D C00I C00C 118.0(3) . . ?
H00j C00I C00C 121.0(2) . . ?
H00j C00I C00D 121.0(2) . . ?
H00k C00J C00G 109.5 . . ?
H00l C00J C00G 109.5 . . ?
H00l C00J H00k 109.5 . . ?
H00m C00J C00G 109.5 . . ?
H00m C00J H00k 109.5 . . ?
H00m C00J H00l 109.5 . . ?
H00n C00K C00G 109.5 . . ?
H00o C00K C00G 109.5 . . ?
H00o C00K H00n 109.5 . . ?
H00p C00K C00G 109.5 . . ?
H00p C00K H00n 109.5 . . ?
H00p C00K H00o 109.5 . . ?
H00q C00L C00G 109.5 . . ?
H00r C00L C00G 109.5 . . ?
H00r C00L H00q 109.5 . . ?
H00s C00L C00G 109.5 . . ?
H00s C00L H00q 109.5 . . ?
H00s C00L H00r 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C006 N005 C00B -2.5(3) . . . . ?
O001 C006 N005 C00F 171.5(3) . . . . ?
F002 C00C C00H C00A -179.2(3) . . . . ?
F002 C00C C00I C00D 179.6(3) . . . . ?
O003 C006 N005 C00B 178.8(3) . . . . ?
O003 C006 N005 C00F -7.2(4) . . . . ?
O004 C007 C008 C009 65.1(3) . . . . ?
O004 C007 C008 C00B -61.6(3) . . . . ?
O004 C007 C00E C00F 62.0(3) . . . . ?
N005 C00B C008 C007 -57.3(3) . . . . ?
N005 C00B C008 C009 176.3(3) . . . . ?
N005 C00F C00E C007 54.0(3) . . . . ?
C007 C008 C009 C00A -82.6(3) . . . . ?
C007 C008 C009 C00D 95.5(3) . . . . ?
C008 C009 C00A C00H -180.0(3) . . . . ?
C008 C009 C00D C00I -179.6(3) . . . . ?
C009 C00A C00H C00C -1.9(4) . . . . ?
C009 C00D C00I C00C 1.0(4) . . . . ?
C00A C00H C00C C00I 1.5(4) . . . . ?


_olex2_exptl_crystal_mounting_method loop
_olex2_submission_original_sample_id 1
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.452
_oxdiff_exptl_absorpt_empirical_full_min 0.491
####################################################################### 
# 
# 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_15-xia_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2mnr68
_database_code_depnum_ccdc_archive 'CCDC 2433010'
loop_
_audit_author_name
_audit_author_address
'Xi Chen'
;Tianjin Institute of Industrial Biotechnology Chinese Academy of Sciences
China
;
_audit_update_record             
;
2025-03-21 deposited with the CCDC.	2025-06-25 downloaded from the CCDC.
;
_audit_creation_date             2025-02-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_chemical_name_systematic        15xia
_chemical_formula_moiety         'C16 H22 F N O3'
_chemical_formula_sum            'C16 H22 F N O3'
_chemical_formula_weight         295.356
_chemical_absolute_configuration ad
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01788 0.00908 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
F 0.07327 0.05351 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.03110 0.01806 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03234 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   6.08342(6)
_cell_length_b                   12.36031(13)
_cell_length_c                   21.0393(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1582.01(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13255
_cell_measurement_temperature    99.9(4)
_cell_measurement_theta_max      74.0150
_cell_measurement_theta_min      3.5670
_exptl_absorpt_coefficient_mu    0.768
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       block
_exptl_crystal_F_000             634.290
_exptl_crystal_preparation       single
_exptl_crystal_recrystallization_method 'vapor diffusion'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9631
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17784
_diffrn_reflns_point_group_measured_fraction_full 0.9979
_diffrn_reflns_point_group_measured_fraction_max 0.9387
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         74.39
_diffrn_reflns_theta_min         4.15
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9631
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -92.00 -31.00   0.50    0.05    --  -77.31 111.00  90.00  122
  2  ω    -85.00 -16.00   0.50    0.05    --  -57.80 125.00  30.00  138
  3  ω    -98.00 -31.00   0.50    0.05    --  -77.31 119.00  15.00  134
  4  ω    -92.00 -31.00   0.50    0.05    --  -77.31 111.00 -30.00  122
  5  ω    -91.00 -32.00   0.50    0.05    --  -77.31 103.00 -68.00  118
  6  ω    -72.00 -12.00   0.50    0.05    --  -57.80 103.00 -68.00  120
  7  ω    -92.00 -31.00   0.50    0.05    --  -77.31 111.00-120.00  122
  8  ω    -92.00 -31.00   0.50    0.05    --  -77.31 111.00-180.00  122
  9  ω   -131.00 -67.00   0.50    0.05    --  -77.31 -24.00   4.00  128
 10  ω   -110.00 -65.00   0.50    0.05    --  -57.80 -30.00  60.00   90
 11  ω   -130.00 -85.00   0.50    0.05    --  -77.31 -30.00 -30.00   90
 12  ω   -121.00 -76.00   0.50    0.05    --  -68.99 -30.00-120.00   90
 13  ω   -121.00 -76.00   0.50    0.05    --  -68.99 -30.00-180.00   90
 14  ω   -130.00 -85.00   0.50    0.05    --  -77.31 -30.00-150.00   90
 15  ω   -110.00 -65.00   0.50    0.05    --  -57.80 -30.00-120.00   90
 16  ω   -130.00 -85.00   0.50    0.05    --  -77.31 -30.00 -60.00   90
 17  ω   -110.00 -72.00   0.50    0.05    --  -57.80 -30.00 -30.00   76
 18  ω   -111.00 -47.00   0.50    0.05    --  -57.80 -24.00   4.00  128
 19  ω   -121.00 -76.00   0.50    0.05    --  -68.99 -30.00 120.00   90
 20  ω   -130.00 -85.00   0.50    0.05    --  -77.31 -30.00 150.00   90
 21  ω     74.00 139.00   0.50    0.05    --   85.54  24.00 169.00  130
 22  ω     92.00 138.00   0.50    0.05    --   85.54  30.00  90.00   92
 23  ω     92.00 138.00   0.50    0.05    --   85.54  30.00 -30.00   92
 24  ω     92.00 138.00   0.50    0.05    --   85.54  30.00 -60.00   92
 25  ω      8.00  78.00   0.50    0.05    --   54.52-119.00 -69.00  140
 26  ω     11.00  63.00   0.50    0.05    --   54.52 -95.00-180.00  104
 27  ω     42.00  92.00   0.50    0.05    --   85.54 -95.00-120.00  100
 28  ω     42.00  92.00   0.50    0.05    --   85.54 -95.00  90.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2237472000
_diffrn_orient_matrix_UB_12      -0.0018801000
_diffrn_orient_matrix_UB_13      -0.0342593000
_diffrn_orient_matrix_UB_21      -0.1138642000
_diffrn_orient_matrix_UB_22      -0.0383495000
_diffrn_orient_matrix_UB_23      -0.0614166000
_diffrn_orient_matrix_UB_31      -0.0331797000
_diffrn_orient_matrix_UB_32      0.1185747000
_diffrn_orient_matrix_UB_33      -0.0203998000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.904
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              26
_reflns_limit_l_min              -25
_reflns_number_gt                2920
_reflns_number_total             3045
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.1579
_refine_diff_density_min         -0.1715
_refine_diff_density_rms         0.0350
_refine_ls_abs_structure_details 
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   -0.08(4)
_refine_ls_d_res_high            0.8005
_refine_ls_d_res_low             10.6573
_refine_ls_goodness_of_fit_ref   0.7816
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3045
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0278
_refine_ls_restrained_S_all      0.7816
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0877
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C008(H008), C00A(H00A)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00b,H00c), C00F(H00g,H00h), C00G(H00i,H00j)
2.c Aromatic/amide H refined with riding coordinates:
 C00H(H00k), C00E(H00f), C00C(H00d), C00D(H00e)
2.d Idealised Me refined as rotating group:
 C00J(H00l,H00m,H00n), C00K(H00o,H00p,H00q), C00L(H00r,H00s,H00t)
2.e Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
F001 F -0.00589(13) 0.61665(6) 0.03015(3) 0.0355(2) Uani 1.000000 .
O002 O 0.22823(13) 0.91496(7) 0.27441(4) 0.02544(19) Uani 1.000000 .
O003 O 0.97827(13) 0.64963(7) 0.39784(4) 0.02534(19) Uani 1.000000 .
O004 O 0.80832(13) 0.51834(6) 0.34050(4) 0.0280(2) Uani 1.000000 .
N005 N 0.72434(17) 0.69618(8) 0.32567(5) 0.0248(2) Uani 1.000000 .
C006 C 0.27940(18) 0.70824(9) 0.19981(5) 0.0215(2) Uani 1.000000 .
C007 C 0.83552(17) 0.61408(9) 0.35370(5) 0.0230(2) Uani 1.000000 .
C008 C 0.42969(18) 0.85662(9) 0.27354(5) 0.0208(2) Uani 1.000000 .
C009 C 0.08838(19) 0.64654(10) 0.08651(5) 0.0258(3) Uani 1.000000 .
C00A C 0.38925(18) 0.73580(9) 0.26249(5) 0.0207(2) Uani 1.000000 .
C00B C 0.54528(19) 0.87234(10) 0.33724(5) 0.0238(2) Uani 1.000000 .
C00C C 0.12184(18) 0.62632(10) 0.19766(5) 0.0233(2) Uani 1.000000 .
C00D C 0.02413(19) 0.59465(10) 0.14102(6) 0.0264(2) Uani 1.000000 .
C00E C 0.3391(2) 0.75764(10) 0.14287(6) 0.0293(3) Uani 1.000000 .
C00F C 0.7629(2) 0.81115(9) 0.33936(6) 0.0261(2) Uani 1.000000 .
C00G C 0.6076(2) 0.67496(9) 0.26634(6) 0.0249(2) Uani 1.000000 .
C00H C 0.2446(2) 0.72709(10) 0.08571(5) 0.0305(3) Uani 1.000000 .
C00I C 1.10079(19) 0.57153(9) 0.43780(5) 0.0251(2) Uani 1.000000 .
C00J C 1.2373(2) 0.49451(11) 0.39758(6) 0.0327(3) Uani 1.000000 .
C00K C 1.2510(2) 0.64589(11) 0.47556(6) 0.0343(3) Uani 1.000000 .
C00L C 0.9397(2) 0.51327(12) 0.48090(6) 0.0337(3) Uani 1.000000 .
H00k H 0.2864(2) 0.76084(10) 0.04699(5) 0.0366(3) Uiso 1.000000 R
H00f H 0.4467(2) 0.81333(10) 0.14323(6) 0.0351(3) Uiso 1.000000 R
H00d H 0.08029(18) 0.59125(10) 0.23601(5) 0.0280(3) Uiso 1.000000 R
H00e H -0.08349(19) 0.53898(10) 0.14006(6) 0.0317(3) Uiso 1.000000 R
H008 H 0.52520(18) 0.88544(9) 0.23876(5) 0.0249(3) Uiso 1.000000 R
H00A H 0.29268(18) 0.70884(9) 0.29754(5) 0.0249(3) Uiso 1.000000 R
H00b H 0.57286(19) 0.95039(10) 0.34419(5) 0.0286(3) Uiso 1.000000 R
H00c H 0.44874(19) 0.84627(10) 0.37188(5) 0.0286(3) Uiso 1.000000 R
H00g H 0.8303(2) 0.81895(9) 0.38193(6) 0.0314(3) Uiso 1.000000 R
H00h H 0.8655(2) 0.84176(9) 0.30757(6) 0.0314(3) Uiso 1.000000 R
H00i H 0.7016(2) 0.69670(9) 0.23013(6) 0.0299(3) Uiso 1.000000 R
H00j H 0.5793(2) 0.59633(9) 0.26266(6) 0.0299(3) Uiso 1.000000 R
H00l H 1.1398(2) 0.4439(5) 0.3755(4) 0.0491(4) Uiso 1.000000 GR
H00m H 1.3220(13) 0.53596(12) 0.3663(3) 0.0491(4) Uiso 1.000000 GR
H00n H 1.3382(12) 0.4541(6) 0.42504(9) 0.0491(4) Uiso 1.000000 GR
H00o H 1.3519(11) 0.6830(6) 0.44652(8) 0.0515(4) Uiso 1.000000 GR
H00p H 1.1622(3) 0.6996(5) 0.4983(4) 0.0515(4) Uiso 1.000000 GR
H00q H 1.3356(13) 0.60311(15) 0.5062(3) 0.0515(4) Uiso 1.000000 GR
H00r H 0.8543(12) 0.56650(12) 0.5050(4) 0.0506(4) Uiso 1.000000 GR
H00s H 0.8401(12) 0.4690(7) 0.45512(7) 0.0506(4) Uiso 1.000000 GR
H00t H 1.0207(3) 0.4667(7) 0.5104(3) 0.0506(4) Uiso 1.000000 GR
H002 H 0.2050(12) 0.9417(10) 0.2383(2) 0.0382(3) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C009 1.3681(13) . ?
O002 C008 1.4220(13) . ?
O002 H002 0.8400 . ?
O003 C007 1.3453(14) . ?
O003 C00I 1.4813(14) . ?
O004 C007 1.2267(15) . ?
N005 C007 1.3547(15) . ?
N005 C00F 1.4687(14) . ?
N005 C00G 1.4599(14) . ?
C006 C00A 1.5172(15) . ?
C006 C00C 1.3950(16) . ?
C006 C00E 1.3929(16) . ?
C008 C00A 1.5313(15) . ?
C008 C00B 1.5259(14) . ?
C008 H008 1.0000 . ?
C009 C00D 1.3707(17) . ?
C009 C00H 1.3764(18) . ?
C00A C00G 1.5284(15) . ?
C00A H00A 1.0000 . ?
C00B C00F 1.5253(16) . ?
C00B H00b 0.9900 . ?
C00B H00c 0.9900 . ?
C00C C00D 1.3881(16) . ?
C00C H00d 0.9500 . ?
C00D H00e 0.9500 . ?
C00E C00H 1.3856(17) . ?
C00E H00f 0.9500 . ?
C00F H00g 0.9900 . ?
C00F H00h 0.9900 . ?
C00G H00i 0.9900 . ?
C00G H00j 0.9900 . ?
C00H H00k 0.9500 . ?
C00I C00J 1.5205(17) . ?
C00I C00K 1.5202(17) . ?
C00I C00L 1.5170(18) . ?
C00J H00l 0.9800 . ?
C00J H00m 0.9800 . ?
C00J H00n 0.9800 . ?
C00K H00o 0.9800 . ?
C00K H00p 0.9800 . ?
C00K H00q 0.9800 . ?
C00L H00r 0.9800 . ?
C00L H00s 0.9800 . ?
C00L H00t 0.9800 . ?

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
H002 O002 C008 109.5 . . ?
C00I O003 C007 120.24(9) . . ?
C00F N005 C007 124.04(10) . . ?
C00G N005 C007 118.72(9) . . ?
C00G N005 C00F 114.79(9) . . ?
C00C C006 C00A 119.59(9) . . ?
C00E C006 C00A 122.29(10) . . ?
C00E C006 C00C 118.01(10) . . ?
O004 C007 O003 123.95(10) . . ?
N005 C007 O003 112.22(10) . . ?
N005 C007 O004 123.83(11) . . ?
C00A C008 O002 110.98(9) . . ?
C00B C008 O002 108.74(9) . . ?
C00B C008 C00A 109.36(9) . . ?
H008 C008 O002 109.25(5) . . ?
H008 C008 C00A 109.25(6) . . ?
H008 C008 C00B 109.25(6) . . ?
C00D C009 F001 118.64(10) . . ?
C00H C009 F001 118.30(10) . . ?
C00H C009 C00D 123.07(11) . . ?
C008 C00A C006 114.94(9) . . ?
C00G C00A C006 108.56(9) . . ?
C00G C00A C008 109.41(9) . . ?
H00A C00A C006 107.90(6) . . ?
H00A C00A C008 107.90(6) . . ?
H00A C00A C00G 107.90(6) . . ?
C00F C00B C008 111.25(9) . . ?
H00b C00B C008 109.38(6) . . ?
H00b C00B C00F 109.38(6) . . ?
H00c C00B C008 109.38(6) . . ?
H00c C00B C00F 109.38(6) . . ?
H00c C00B H00b 108.0 . . ?
C00D C00C C006 121.78(10) . . ?
H00d C00C C006 119.11(6) . . ?
H00d C00C C00D 119.11(7) . . ?
C00C C00D C009 117.66(11) . . ?
H00e C00D C009 121.17(7) . . ?
H00e C00D C00C 121.17(7) . . ?
C00H C00E C006 121.25(11) . . ?
H00f C00E C006 119.38(7) . . ?
H00f C00E C00H 119.38(7) . . ?
C00B C00F N005 109.60(10) . . ?
H00g C00F N005 109.75(6) . . ?
H00g C00F C00B 109.75(6) . . ?
H00h C00F N005 109.75(7) . . ?
H00h C00F C00B 109.75(6) . . ?
H00h C00F H00g 108.2 . . ?
C00A C00G N005 112.32(9) . . ?
H00i C00G N005 109.14(6) . . ?
H00i C00G C00A 109.14(6) . . ?
H00j C00G N005 109.14(6) . . ?
H00j C00G C00A 109.14(6) . . ?
H00j C00G H00i 107.9 . . ?
C00E C00H C009 118.23(10) . . ?
H00k C00H C009 120.89(6) . . ?
H00k C00H C00E 120.89(7) . . ?
C00J C00I O003 111.54(9) . . ?
C00K C00I O003 101.83(9) . . ?
C00K C00I C00J 109.95(11) . . ?
C00L C00I O003 108.88(9) . . ?
C00L C00I C00J 112.85(10) . . ?
C00L C00I C00K 111.27(11) . . ?
H00l C00J C00I 109.5 . . ?
H00m C00J C00I 109.5 . . ?
H00m C00J H00l 109.5 . . ?
H00n C00J C00I 109.5 . . ?
H00n C00J H00l 109.5 . . ?
H00n C00J H00m 109.5 . . ?
H00o C00K C00I 109.5 . . ?
H00p C00K C00I 109.5 . . ?
H00p C00K H00o 109.5 . . ?
H00q C00K C00I 109.5 . . ?
H00q C00K H00o 109.5 . . ?
H00q C00K H00p 109.5 . . ?
H00r C00L C00I 109.5 . . ?
H00s C00L C00I 109.5 . . ?
H00s C00L H00r 109.5 . . ?
H00t C00L C00I 109.5 . . ?
H00t C00L H00r 109.5 . . ?
H00t C00L H00s 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F001 C009 C00D C00C -179.97(10) . . . . ?
F001 C009 C00H C00E 179.69(11) . . . . ?
O002 C008 C00A C006 61.38(9) . . . . ?
O002 C008 C00A C00G -176.20(9) . . . . ?
O002 C008 C00B C00F 179.79(8) . . . . ?
O003 C007 N005 C00F 2.99(12) . . . . ?
O003 C007 N005 C00G 164.23(9) . . . . ?
O004 C007 N005 C00F -177.31(11) . . . . ?
O004 C007 N005 C00G -16.06(14) . . . . ?
N005 C00F C00B C008 -56.02(11) . . . . ?
N005 C00G C00A C006 -179.56(9) . . . . ?
N005 C00G C00A C008 54.28(10) . . . . ?
C006 C00A C008 C00B -178.66(9) . . . . ?
C006 C00C C00D C009 0.27(13) . . . . ?
C006 C00E C00H C009 0.28(15) . . . . ?


_olex2_exptl_crystal_mounting_method loop
_olex2_submission_original_sample_id 15xia
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.697
_oxdiff_exptl_absorpt_empirical_full_min 0.551
####################################################################### 
# 
# 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_17xia_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2mp04h
_database_code_depnum_ccdc_archive 'CCDC 2433256'
loop_
_audit_author_name
_audit_author_address
'Xi Chen'
;Tianjin Institute of Industrial Biotechnology Chinese Academy of Sciences
China
;
_audit_update_record             
;
2025-03-22 deposited with the CCDC.	2025-06-25 downloaded from the CCDC.
;
_audit_creation_date             2025-02-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_chemical_name_systematic        17
_chemical_formula_moiety         'C16 H22 F N O3'
_chemical_formula_sum            'C16 H22 F N O3'
_chemical_formula_weight         295.356
_chemical_absolute_configuration ad
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01788 0.00908 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
F 0.07327 0.05351 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.03110 0.01806 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03234 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   6.0869(1)
_cell_length_b                   12.3980(1)
_cell_length_c                   20.9757(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1582.94(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13369
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1980
_cell_measurement_theta_min      4.1150
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       block
_exptl_crystal_F_000             634.290
_exptl_crystal_preparation       'single crystal'
_exptl_crystal_recrystallization_method 'vapor diffusion'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9752
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17980
_diffrn_reflns_point_group_measured_fraction_full 0.9972
_diffrn_reflns_point_group_measured_fraction_max 0.9507
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         74.50
_diffrn_reflns_theta_min         4.14
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9752
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     61.00 107.00   0.50    0.05    --   54.52  30.00 120.00   92
  2  ω     85.00 131.00   0.50    0.05    --   78.29  30.00  30.00   92
  3  ω     72.00 118.00   0.50    0.05    --   65.77  30.00   0.00   92
  4  ω     92.00 138.00   0.50    0.05    --   85.54  30.00 -90.00   92
  5  ω     85.00 131.00   0.50    0.05    --   78.29  30.00-150.00   92
  6  ω     85.00 131.00   0.50    0.05    --   78.29  30.00-120.00   92
  7  ω     55.00 107.00   0.50    0.05    --   54.52  27.00 -35.00  104
  8  ω     86.00 138.00   0.50    0.05    --   85.54  27.00 -35.00  104
  9  ω     92.00 138.00   0.50    0.05    --   85.54  30.00   0.00   92
 10  ω     92.00 138.00   0.50    0.05    --   85.54  30.00 150.00   92
 11  ω     39.00  93.00   0.50    0.05    --   85.54-110.00  69.00  108
 12  ω     42.00  92.00   0.50    0.05    --   85.54 -95.00  90.00  100
 13  ω      9.00  69.00   0.50    0.05    --   54.52-104.00 -27.00  120
 14  ω     11.00  63.00   0.50    0.05    --   54.52 -95.00 -90.00  104
 15  ω     42.00  92.00   0.50    0.05    --   85.54 -95.00-150.00  100
 16  ω     33.00  92.00   0.50    0.05    --   78.29-104.00 -27.00  118
 17  ω     35.00  86.00   0.50    0.05    --   78.29 -95.00   0.00  102
 18  ω     11.00  63.00   0.50    0.05    --   54.52 -95.00  30.00  104
 19  ω     11.00  36.00   0.50    0.05    --   54.52 -95.00  90.00   50
 20  ω   -110.00 -65.00   0.50    0.05    --  -57.80 -30.00-150.00   90
 21  ω   -130.00 -85.00   0.50    0.05    --  -77.31 -30.00  30.00   90
 22  ω   -130.00 -85.00   0.50    0.05    --  -77.31 -30.00  60.00   90
 23  ω   -121.00 -76.00   0.50    0.05    --  -68.99 -30.00  90.00   90
 24  ω   -121.00 -76.00   0.50    0.05    --  -68.99 -30.00 120.00   90
 25  ω   -130.00 -80.00   0.50    0.05    --  -77.31 -27.00 161.00  100
 26  ω   -110.00 -61.00   0.50    0.05    --  -57.80 -27.00 161.00   98
 27  ω    -92.00 -31.00   0.50    0.05    --  -77.31 111.00 120.00  122
 28  ω    -87.00 -22.00   0.50    0.05    --  -68.99 110.00 164.00  130
 29  ω    -92.00 -31.00   0.50    0.05    --  -77.31 111.00  60.00  122
 30  ω    -92.00 -31.00   0.50    0.05    --  -77.31 111.00-120.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0429747000
_diffrn_orient_matrix_UB_12      -0.1092026000
_diffrn_orient_matrix_UB_13      -0.0327586000
_diffrn_orient_matrix_UB_21      -0.0781502000
_diffrn_orient_matrix_UB_22      -0.0475287000
_diffrn_orient_matrix_UB_23      0.0639525000
_diffrn_orient_matrix_UB_31      -0.2368863000
_diffrn_orient_matrix_UB_32      0.0354438000
_diffrn_orient_matrix_UB_33      -0.0151638000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.916
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              26
_reflns_limit_l_min              -25
_reflns_number_gt                2959
_reflns_number_total             3083
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.1224
_refine_diff_density_min         -0.1718
_refine_diff_density_rms         0.0339
_refine_ls_abs_structure_details 
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             10.6730
_refine_ls_goodness_of_fit_ref   1.0381
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3083
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0293
_refine_ls_restrained_S_all      1.0381
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0511P)²+0.1634P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0787
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009), C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00C(H00a,H00c), C00F(H00f,H00g), C00G(H00h,H00i)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C00D(H00D), C00E(H00E), C00H(H00j)
2.d Idealised Me refined as rotating group:
 C00J(H00k,H00l,H00m), C00K(H00n,H00o,H00p), C00L(H00q,H00r,H00s)
2.e Idealised tetrahedral OH refined as rotating group:
 O004(H004)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
F001 F 1.00845(14) 0.61636(7) 0.03000(3) 0.0364(2) Uani 1.000000 .
O002 O 0.02119(14) 0.64971(7) 0.39773(4) 0.0261(2) Uani 1.000000 .
O003 O 0.19239(15) 0.51877(7) 0.34055(4) 0.0288(2) Uani 1.000000 .
O004 O 0.77016(15) 0.91490(7) 0.27453(4) 0.0266(2) Uani 1.000000 .
H004 H 0.7916(14) 0.9435(11) 0.2387(2) 0.0398(3) Uiso 1.000000 GR
N005 N 0.27470(18) 0.69611(8) 0.32552(5) 0.0259(2) Uani 1.000000 .
C006 C 0.7214(2) 0.70849(10) 0.19976(5) 0.0223(2) Uani 1.000000 .
C007 C 0.16458(19) 0.61431(10) 0.35345(6) 0.0240(3) Uani 1.000000 .
C008 C 0.8776(2) 0.62635(10) 0.19776(6) 0.0241(3) Uani 1.000000 .
H008 H 0.9178(2) 0.59121(10) 0.23627(6) 0.0289(3) Uiso 1.000000 R
C009 C 0.6110(2) 0.73620(10) 0.26243(6) 0.0216(3) Uani 1.000000 .
H009 H 0.7074(2) 0.70963(10) 0.29771(6) 0.0259(3) Uiso 1.000000 R
C00A C 0.9133(2) 0.64639(10) 0.08638(6) 0.0266(3) Uani 1.000000 .
C00B C 0.5692(2) 0.85647(10) 0.27340(6) 0.0220(3) Uani 1.000000 .
H00B H 0.4742(2) 0.88496(10) 0.23835(6) 0.0264(3) Uiso 1.000000 R
C00C C 0.4528(2) 0.87212(10) 0.33700(6) 0.0251(3) Uani 1.000000 .
H00a H 0.5490(2) 0.84639(10) 0.37190(6) 0.0301(3) Uiso 1.000000 R
H00c H 0.4247(2) 0.94991(10) 0.34385(6) 0.0301(3) Uiso 1.000000 R
C00D C 0.9760(2) 0.59440(11) 0.14121(6) 0.0273(3) Uani 1.000000 .
H00D H 1.0829(2) 0.53858(11) 0.14046(6) 0.0328(3) Uiso 1.000000 R
C00E C 0.6640(2) 0.75801(11) 0.14269(6) 0.0303(3) Uani 1.000000 .
H00E H 0.5574(2) 0.81399(11) 0.14294(6) 0.0364(4) Uiso 1.000000 R
C00F C 0.2358(2) 0.81086(10) 0.33898(6) 0.0272(3) Uani 1.000000 .
H00f H 0.1336(2) 0.84110(10) 0.30692(6) 0.0326(3) Uiso 1.000000 R
H00g H 0.1677(2) 0.81883(10) 0.38159(6) 0.0326(3) Uiso 1.000000 R
C00G C 0.3929(2) 0.67480(10) 0.26611(6) 0.0259(3) Uani 1.000000 .
H00h H 0.4222(2) 0.59647(10) 0.26265(6) 0.0311(3) Uiso 1.000000 R
H00i H 0.2993(2) 0.69597(10) 0.22960(6) 0.0311(3) Uiso 1.000000 R
C00H C 0.7590(2) 0.72740(11) 0.08540(6) 0.0313(3) Uani 1.000000 .
H00j H 0.7187(2) 0.76144(11) 0.04655(6) 0.0376(4) Uiso 1.000000 R
C00I C -0.1013(2) 0.57173(11) 0.43782(6) 0.0263(3) Uani 1.000000 .
C00J C -0.2520(3) 0.64559(12) 0.47550(7) 0.0358(3) Uani 1.000000 .
H00k H -0.1639(3) 0.6993(6) 0.4983(4) 0.0537(5) Uiso 1.000000 GR
H00l H -0.3530(12) 0.6823(7) 0.44628(9) 0.0537(5) Uiso 1.000000 GR
H00m H -0.3364(13) 0.60285(16) 0.5062(4) 0.0537(5) Uiso 1.000000 GR
C00K C -0.2369(2) 0.49463(12) 0.39735(7) 0.0338(3) Uani 1.000000 .
H00n H -0.3188(14) 0.53564(14) 0.3653(3) 0.0506(5) Uiso 1.000000 GR
H00o H -0.1391(3) 0.4432(6) 0.3760(4) 0.0506(5) Uiso 1.000000 GR
H00p H -0.3401(13) 0.4554(7) 0.42468(10) 0.0506(5) Uiso 1.000000 GR
C00L C 0.0596(3) 0.51367(12) 0.48101(7) 0.0345(3) Uani 1.000000 .
H00q H 0.1592(12) 0.4696(7) 0.45513(8) 0.0517(5) Uiso 1.000000 GR
H00r H 0.1450(13) 0.56673(12) 0.5052(4) 0.0517(5) Uiso 1.000000 GR
H00s H -0.0213(3) 0.4672(7) 0.5106(4) 0.0517(5) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C00A 1.3683(14) . ?
O002 C007 1.3479(15) . ?
O002 C00I 1.4824(15) . ?
O003 C007 1.2267(16) . ?
O004 H004 0.8400 . ?
O004 C00B 1.4218(14) . ?
N005 C007 1.3495(16) . ?
N005 C00F 1.4696(16) . ?
N005 C00G 1.4631(16) . ?
C006 C008 1.3938(18) . ?
C006 C009 1.5155(16) . ?
C006 C00E 1.3900(17) . ?
C008 H008 0.9500 . ?
C008 C00D 1.3865(18) . ?
C009 H009 1.0000 . ?
C009 C00B 1.5301(17) . ?
C009 C00G 1.5323(17) . ?
C00A C00D 1.3726(19) . ?
C00A C00H 1.375(2) . ?
C00B H00B 1.0000 . ?
C00B C00C 1.5230(16) . ?
C00C H00a 0.9900 . ?
C00C H00c 0.9900 . ?
C00C C00F 1.5243(17) . ?
C00D H00D 0.9500 . ?
C00E H00E 0.9500 . ?
C00E C00H 1.3869(18) . ?
C00F H00f 0.9900 . ?
C00F H00g 0.9900 . ?
C00G H00h 0.9900 . ?
C00G H00i 0.9900 . ?
C00H H00j 0.9500 . ?
C00I C00J 1.5182(19) . ?
C00I C00K 1.5218(19) . ?
C00I C00L 1.5159(19) . ?
C00J H00k 0.9800 . ?
C00J H00l 0.9800 . ?
C00J H00m 0.9800 . ?
C00K H00n 0.9800 . ?
C00K H00o 0.9800 . ?
C00K H00p 0.9800 . ?
C00L H00q 0.9800 . ?
C00L H00r 0.9800 . ?
C00L H00s 0.9800 . ?

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
C00I O002 C007 120.27(10) . . ?
C00B O004 H004 109.5 . . ?
C00F N005 C007 124.34(11) . . ?
C00G N005 C007 118.58(10) . . ?
C00G N005 C00F 114.69(10) . . ?
C009 C006 C008 119.61(10) . . ?
C00E C006 C008 117.92(11) . . ?
C00E C006 C009 122.37(11) . . ?
O003 C007 O002 123.77(11) . . ?
N005 C007 O002 112.09(11) . . ?
N005 C007 O003 124.14(12) . . ?
H008 C008 C006 119.02(7) . . ?
C00D C008 C006 121.96(11) . . ?
C00D C008 H008 119.02(7) . . ?
H009 C009 C006 107.90(6) . . ?
C00B C009 C006 115.16(10) . . ?
C00B C009 H009 107.90(6) . . ?
C00G C009 C006 108.36(10) . . ?
C00G C009 H009 107.90(7) . . ?
C00G C009 C00B 109.41(10) . . ?
C00D C00A F001 118.61(11) . . ?
C00H C00A F001 118.34(11) . . ?
C00H C00A C00D 123.04(12) . . ?
C009 C00B O004 110.84(9) . . ?
H00B C00B O004 109.27(6) . . ?
H00B C00B C009 109.27(6) . . ?
C00C C00B O004 108.71(10) . . ?
C00C C00B C009 109.47(10) . . ?
C00C C00B H00B 109.27(6) . . ?
H00a C00C C00B 109.37(6) . . ?
H00c C00C C00B 109.37(7) . . ?
H00c C00C H00a 108.0 . . ?
C00F C00C C00B 111.31(10) . . ?
C00F C00C H00a 109.37(7) . . ?
C00F C00C H00c 109.37(7) . . ?
C00A C00D C008 117.56(12) . . ?
H00D C00D C008 121.22(7) . . ?
H00D C00D C00A 121.22(8) . . ?
H00E C00E C006 119.32(7) . . ?
C00H C00E C006 121.37(12) . . ?
C00H C00E H00E 119.32(8) . . ?
C00C C00F N005 109.72(11) . . ?
H00f C00F N005 109.72(7) . . ?
H00f C00F C00C 109.72(7) . . ?
H00g C00F N005 109.72(7) . . ?
H00g C00F C00C 109.72(7) . . ?
H00g C00F H00f 108.2 . . ?
C009 C00G N005 112.29(10) . . ?
H00h C00G N005 109.14(7) . . ?
H00h C00G C009 109.14(7) . . ?
H00i C00G N005 109.14(7) . . ?
H00i C00G C009 109.14(7) . . ?
H00i C00G H00h 107.9 . . ?
C00E C00H C00A 118.16(11) . . ?
H00j C00H C00A 120.92(7) . . ?
H00j C00H C00E 120.92(8) . . ?
C00J C00I O002 101.88(10) . . ?
C00K C00I O002 111.47(10) . . ?
C00K C00I C00J 109.97(12) . . ?
C00L C00I O002 108.90(11) . . ?
C00L C00I C00J 111.45(12) . . ?
C00L C00I C00K 112.68(12) . . ?
H00k C00J C00I 109.5 . . ?
H00l C00J C00I 109.5 . . ?
H00l C00J H00k 109.5 . . ?
H00m C00J C00I 109.5 . . ?
H00m C00J H00k 109.5 . . ?
H00m C00J H00l 109.5 . . ?
H00n C00K C00I 109.5 . . ?
H00o C00K C00I 109.5 . . ?
H00o C00K H00n 109.5 . . ?
H00p C00K C00I 109.5 . . ?
H00p C00K H00n 109.5 . . ?
H00p C00K H00o 109.5 . . ?
H00q C00L C00I 109.5 . . ?
H00r C00L C00I 109.5 . . ?
H00r C00L H00q 109.5 . . ?
H00s C00L C00I 109.5 . . ?
H00s C00L H00q 109.5 . . ?
H00s C00L H00r 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F001 C00A C00D C008 179.91(11) . . . . ?
F001 C00A C00H C00E -179.64(12) . . . . ?
O002 C007 N005 C00F -3.06(13) . . . . ?
O002 C007 N005 C00G -164.53(10) . . . . ?
O003 C007 N005 C00F 177.45(13) . . . . ?
O003 C007 N005 C00G 15.98(15) . . . . ?
O004 C00B C009 C006 -61.59(11) . . . . ?
O004 C00B C009 C00G 176.11(10) . . . . ?
O004 C00B C00C C00F -179.75(9) . . . . ?
N005 C00F C00C C00B 56.09(12) . . . . ?
N005 C00G C009 C006 179.64(10) . . . . ?
N005 C00G C009 C00B -54.08(11) . . . . ?
C006 C008 C00D C00A -0.35(15) . . . . ?
C006 C009 C00B C00C 178.50(10) . . . . ?
C006 C00E C00H C00A -0.20(16) . . . . ?
C008 C00D C00A C00H -0.13(16) . . . . ?
C009 C00B C00C C00F -58.54(11) . . . . ?


_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.926
_oxdiff_exptl_absorpt_empirical_full_min 0.649
####################################################################### 
# 
# 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_exp_604_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2mbsxp
_database_code_depnum_ccdc_archive 'CCDC 2423453'
loop_
_audit_author_name
_audit_author_address
'Xi Chen'
;Tianjin Institute of Industrial Biotechnology Chinese Academy of Sciences
China
;
_audit_update_record             
;
2025-02-13 deposited with the CCDC.	2025-06-25 downloaded from the CCDC.
;
_audit_creation_date             2024-01-26
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1
_chemical_formula_moiety         'C16 H22 N O3'
_chemical_formula_sum            'C16 H22 N O3'
_chemical_formula_weight         276.34
_chemical_absolute_configuration ?
_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                   6.2527(6)
_cell_length_b                   13.3719(10)
_cell_length_c                   18.7005(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1563.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6915
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      68.9890
_cell_measurement_theta_min      3.9480
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.938
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0967
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17485
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.339
_diffrn_reflns_theta_min         5.774
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     85.00 131.00   0.50    0.50    --   78.20  30.00 150.00   92
  2  ω     92.00 138.00   0.50    0.50    --   85.54  30.00-120.00   92
  3  ω     73.00 118.00   0.50    0.50    --   65.83  30.00-150.00   90
  4  ω    -96.00 -33.00   0.50    0.50    --  -82.00 111.00-150.00  126
  5  ω    -98.00 -20.00   0.50    0.50    --  -69.06 125.00-120.00  156
  6  ω    -97.00 -28.00   0.50    0.50    --  -77.27 111.00   0.00  138
  7  ω    -67.00 -13.00   0.50    0.50    --  -57.83  97.00  98.00  108
  8  ω    -87.00 -33.00   0.50    0.50    --  -77.27  97.00  98.00  108
  9  ω    -91.00 -37.00   0.50    0.50    --  -82.00  97.00  98.00  108
 10  ω    -97.00 -55.00   0.50    0.50    --  -77.27 111.00 150.00   84
 11  ω    -78.00 -25.00   0.50    0.50    --  -69.06  97.00  98.00  106
 12  ω   -110.00 -65.00   0.50    0.50    --  -57.83 -30.00 -30.00   90
 13  ω   -130.00 -85.00   0.50    0.50    --  -77.27 -30.00 -30.00   90
 14  ω   -134.00 -89.00   0.50    0.50    --  -82.00 -30.00   0.00   90
 15  ω   -134.00 -89.00   0.50    0.50    --  -82.00 -30.00 -90.00   90
 16  ω   -130.00 -85.00   0.50    0.50    --  -77.27 -30.00  30.00   90
 17  ω   -130.00 -85.00   0.50    0.50    --  -77.27 -30.00  60.00   90
 18  ω   -130.00 -85.00   0.50    0.50    --  -77.27 -30.00 120.00   90
 19  ω   -110.00 -65.00   0.50    0.50    --  -57.83 -30.00 150.00   90
 20  ω   -110.00 -65.00   0.50    0.50    --  -57.83 -30.00  60.00   90
 21  ω   -130.00 -85.00   0.50    0.50    --  -77.27 -30.00 -60.00   90
 22  ω   -130.00 -85.00   0.50    0.50    --  -77.27 -30.00-120.00   90
 23  ω     22.00  74.00   0.50    0.50    --   65.83 -95.00-180.00  104
 24  ω     11.00  63.00   0.50    0.50    --   54.56 -95.00-120.00  104
 25  ω     10.00  65.00   0.50    0.50    --   54.56 -97.00  -9.00  110
 26  ω     22.00  76.00   0.50    0.50    --   65.83 -97.00  -9.00  108
 27  ω     34.00  89.00   0.50    0.50    --   78.20 -97.00  -9.00  110
 28  ω     41.00  93.00   0.50    0.50    --   85.54 -97.00  -9.00  104
 29  ω     11.00  63.00   0.50    0.50    --   54.56 -95.00  90.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1643441000
_diffrn_orient_matrix_UB_12      0.0766221000
_diffrn_orient_matrix_UB_13      0.0277174000
_diffrn_orient_matrix_UB_21      0.1634579000
_diffrn_orient_matrix_UB_22      -0.0372298000
_diffrn_orient_matrix_UB_23      -0.0555158000
_diffrn_orient_matrix_UB_31      -0.0841462000
_diffrn_orient_matrix_UB_32      0.0774751000
_diffrn_orient_matrix_UB_33      -0.0541458000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.897
_reflns_number_gt                2280
_reflns_number_total             2905
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 808 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(19)
_refine_ls_extinction_coef       0.0086(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2905
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.021
_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)+(0.0870P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1359
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C1(H1A,H1B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C8(H8), C11(H11), C10(H10), C9(H9)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O14 O 0.0209(4) 0.63912(14) 0.39139(11) 0.0613(6) Uani 1 1 d . . . . .
O20 O 0.7462(4) 0.89115(14) 0.27235(11) 0.0648(6) Uani 1 1 d . . . . .
O19 O 0.2271(4) 0.51938(14) 0.33990(11) 0.0681(6) Uani 1 1 d . . . . .
N6 N 0.2619(4) 0.68264(16) 0.30915(13) 0.0607(7) Uani 1 1 d . . . . .
C7 C 0.7451(5) 0.69733(18) 0.18816(14) 0.0501(6) Uani 1 1 d . . . . .
C13 C 0.1736(5) 0.6074(2) 0.34632(16) 0.0557(7) Uani 1 1 d . . . . .
C3 C 0.5551(5) 0.83464(18) 0.26112(16) 0.0517(7) Uani 1 1 d . . . . .
H3 H 0.483039 0.858984 0.216656 0.062 Uiso 1 1 calc R U . . .
C2 C 0.6095(5) 0.72430(18) 0.25237(14) 0.0486(7) Uani 1 1 d . . . . .
H2 H 0.689573 0.702996 0.296077 0.058 Uiso 1 1 calc R U . . .
C4 C 0.4068(5) 0.84968(19) 0.32388(16) 0.0598(8) Uani 1 1 d . . . . .
H4A H 0.369076 0.921411 0.327445 0.072 Uiso 1 1 calc R U . . .
H4B H 0.482062 0.830568 0.368410 0.072 Uiso 1 1 calc R U . . .
C12 C 0.8641(5) 0.60990(19) 0.18948(16) 0.0549(7) Uani 1 1 d . . . . .
H12 H 0.862948 0.569921 0.231474 0.066 Uiso 1 1 calc R U . . .
C8 C 0.7504(7) 0.7544(2) 0.12576(17) 0.0721(9) Uani 1 1 d . . . . .
H8 H 0.670341 0.814672 0.123033 0.087 Uiso 1 1 calc R U . . .
C15 C -0.0908(5) 0.5690(2) 0.43948(16) 0.0613(8) Uani 1 1 d . . . . .
C11 C 0.9852(6) 0.5790(2) 0.13109(16) 0.0631(8) Uani 1 1 d . . . . .
H11 H 1.065499 0.518736 0.133273 0.076 Uiso 1 1 calc R U . . .
C1 C 0.4033(5) 0.6622(2) 0.24899(17) 0.0608(8) Uani 1 1 d . . . . .
H1A H 0.327232 0.677281 0.203835 0.073 Uiso 1 1 calc R U . . .
H1B H 0.440577 0.590236 0.248745 0.073 Uiso 1 1 calc R U . . .
C5 C 0.2030(5) 0.7884(2) 0.31724(19) 0.0651(8) Uani 1 1 d . . . . .
H5A H 0.113521 0.797331 0.360450 0.078 Uiso 1 1 calc R U . . .
H5B H 0.119768 0.810856 0.275165 0.078 Uiso 1 1 calc R U . . .
C10 C 0.9873(6) 0.6369(2) 0.06995(17) 0.0679(8) Uani 1 1 d . . . . .
H10 H 1.068479 0.616443 0.029568 0.082 Uiso 1 1 calc R U . . .
C16 C -0.2085(7) 0.4896(3) 0.3963(2) 0.0805(10) Uani 1 1 d . . . . .
H16A H -0.294051 0.522022 0.358978 0.121 Uiso 1 1 calc R U . . .
H16B H -0.302676 0.451361 0.427986 0.121 Uiso 1 1 calc R U . . .
H16C H -0.104428 0.444468 0.374086 0.121 Uiso 1 1 calc R U . . .
C9 C 0.8716(8) 0.7239(3) 0.06777(18) 0.0823(11) Uani 1 1 d . . . . .
H9 H 0.874695 0.763929 0.025811 0.099 Uiso 1 1 calc R U . . .
C18 C -0.2486(7) 0.6375(3) 0.47673(19) 0.0804(10) Uani 1 1 d . . . . .
H18A H -0.171090 0.692375 0.499896 0.121 Uiso 1 1 calc R U . . .
H18B H -0.328033 0.599588 0.512848 0.121 Uiso 1 1 calc R U . . .
H18C H -0.348783 0.664968 0.441506 0.121 Uiso 1 1 calc R U . . .
C17 C 0.0671(7) 0.5244(3) 0.4917(2) 0.0844(11) Uani 1 1 d . . . . .
H17A H 0.164256 0.479323 0.466171 0.127 Uiso 1 1 calc R U . . .
H17B H -0.010296 0.486925 0.528521 0.127 Uiso 1 1 calc R U . . .
H17C H 0.149781 0.578137 0.514208 0.127 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
O14 C13 1.342(4) . ?
O14 C15 1.475(4) . ?
O20 C3 1.429(4) . ?
O19 C13 1.229(3) . ?
N6 C13 1.342(4) . ?
N6 C1 1.457(4) . ?
N6 C5 1.469(4) . ?
C7 C2 1.514(4) . ?
C7 C12 1.386(4) . ?
C7 C8 1.395(4) . ?
C3 C2 1.523(3) . ?
C3 C4 1.509(4) . ?
C2 C1 1.535(4) . ?
C4 C5 1.520(5) . ?
C12 C11 1.392(4) . ?
C8 C9 1.384(5) . ?
C15 C16 1.523(5) . ?
C15 C18 1.516(5) . ?
C15 C17 1.511(5) . ?
C11 C10 1.381(5) . ?
C10 C9 1.371(5) . ?

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 O14 C15 121.2(2) . . ?
C13 N6 C1 120.6(2) . . ?
C13 N6 C5 124.4(3) . . ?
C1 N6 C5 114.4(2) . . ?
C12 C7 C2 119.2(2) . . ?
C12 C7 C8 117.6(3) . . ?
C8 C7 C2 123.1(3) . . ?
O19 C13 O14 123.9(3) . . ?
O19 C13 N6 123.7(3) . . ?
N6 C13 O14 112.4(2) . . ?
O20 C3 C2 109.9(2) . . ?
O20 C3 C4 109.2(2) . . ?
C4 C3 C2 110.5(2) . . ?
C7 C2 C3 116.2(2) . . ?
C7 C2 C1 108.0(2) . . ?
C3 C2 C1 109.9(2) . . ?
C3 C4 C5 112.3(2) . . ?
C7 C12 C11 121.9(3) . . ?
C9 C8 C7 120.5(3) . . ?
O14 C15 C16 110.4(2) . . ?
O14 C15 C18 101.8(2) . . ?
O14 C15 C17 109.6(3) . . ?
C18 C15 C16 110.5(3) . . ?
C17 C15 C16 112.5(3) . . ?
C17 C15 C18 111.5(3) . . ?
C10 C11 C12 119.2(3) . . ?
N6 C1 C2 112.1(2) . . ?
N6 C5 C4 108.5(3) . . ?
C9 C10 C11 119.7(3) . . ?
C10 C9 C8 121.0(3) . . ?


_olex2_submission_original_sample_id chenjing20240126
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 3.069
_oxdiff_exptl_absorpt_empirical_full_min 0.281
