# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_syn-3a
_database_code_depnum_ccdc_archive 'CCDC 1942738'
loop_
_audit_author_name
_audit_author_address
Fu
;HuaQiao University
China
;
_audit_update_record             
;
2019-11-04 deposited with the CCDC.	2019-12-06 downloaded from the CCDC.
;
_audit_creation_date             2019-11-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 N2 O4'
_chemical_formula_sum            'C22 H22 N2 O4'
_chemical_formula_weight         378.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.7113(9)
_cell_length_b                   9.7397(5)
_cell_length_c                   14.7226(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.505(6)
_cell_angle_gamma                90
_cell_volume                     1919.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1701
_cell_measurement_temperature    293.1(2)
_cell_measurement_theta_max      25.8460
_cell_measurement_theta_min      4.4520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8543
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.326
_diffrn_reflns_theta_min         3.523
_diffrn_ambient_temperature      293.1(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.833
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -38.00  25.00   1.00    7.50    --   15.49 -38.00  30.00   63
  2  ω    -14.00  59.00   1.00    7.50    --   15.49  19.00 -90.00   73
  3  ω    -36.00  -9.00   1.00    7.50    --   15.49 -57.00 -90.00   27
  4  ω     37.00  82.00   1.00    7.50    --   15.49 178.00-150.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0206557000
_diffrn_orient_matrix_UB_12      -0.0516707000
_diffrn_orient_matrix_UB_13      -0.0324728000
_diffrn_orient_matrix_UB_21      0.0479229000
_diffrn_orient_matrix_UB_22      -0.0127100000
_diffrn_orient_matrix_UB_23      -0.0090568000
_diffrn_orient_matrix_UB_31      0.0092259000
_diffrn_orient_matrix_UB_32      -0.0497067000
_diffrn_orient_matrix_UB_33      0.0360569000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2512
_reflns_number_total             4391
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         4391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1199
_refine_ls_R_factor_gt           0.0629
_refine_ls_restrained_S_all      1.026
_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)+(0.0580P)²+0.1125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1471
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C21(H21), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C5(H5), C13(H13), C16(H16), C4(H4), C9(H9), C19(H19),
 C14(H14), C15(H15)
2.d X=CH2 refined with riding coordinates:
 C20(H20A,H20B), C10(H10A,H10B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.72107(12) 0.78112(15) 0.39023(9) 0.0488(4) Uani 1 1 d . . . . .
O3 O 0.79266(11) 0.29674(15) 0.58276(10) 0.0504(4) Uani 1 1 d . . . . .
O2 O 0.85948(12) 0.65112(16) 0.42545(10) 0.0530(4) Uani 1 1 d . . . . .
O4 O 0.81886(12) 0.35439(16) 0.44234(10) 0.0537(4) Uani 1 1 d . . . . .
N1 N 0.88561(15) 0.55991(19) 0.60411(14) 0.0479(5) Uani 1 1 d . . . . .
N2 N 0.65993(16) 0.4983(2) 0.34009(13) 0.0477(5) Uani 1 1 d . . . . .
C12 C 0.65189(16) 0.3346(2) 0.46305(13) 0.0409(5) Uani 1 1 d . . . . .
C1 C 0.85013(15) 0.6866(2) 0.62026(14) 0.0387(5) Uani 1 1 d . . . . .
C2 C 0.80815(15) 0.7750(2) 0.54600(13) 0.0390(5) Uani 1 1 d . . . . .
C21 C 0.91417(16) 0.4523(2) 0.67240(14) 0.0436(5) Uani 1 1 d . . . . .
H21 H 0.870583 0.458165 0.716955 0.052 Uiso 1 1 calc R . . . .
C11 C 0.60537(16) 0.4192(2) 0.38775(14) 0.0419(5) Uani 1 1 d . . . . .
C6 C 0.85065(16) 0.7313(2) 0.71071(14) 0.0426(5) Uani 1 1 d . . . . .
H6 H 0.876865 0.674642 0.760926 0.051 Uiso 1 1 calc R . . . .
C17 C 0.76145(17) 0.3296(2) 0.49172(14) 0.0411(5) Uani 1 1 d . . . . .
C7 C 0.80121(17) 0.7296(2) 0.44970(14) 0.0421(5) Uani 1 1 d . . . . .
C3 C 0.77136(17) 0.9029(2) 0.56463(15) 0.0483(6) Uani 1 1 d . . . . .
H3 H 0.743985 0.960676 0.515394 0.058 Uiso 1 1 calc R . . . .
C5 C 0.81297(17) 0.8575(2) 0.72625(15) 0.0488(6) Uani 1 1 d . . . . .
H5 H 0.813238 0.884479 0.786900 0.059 Uiso 1 1 calc R . . . .
C18 C 0.62095(17) 0.6177(2) 0.28470(14) 0.0468(6) Uani 1 1 d . . . . .
H18 H 0.565215 0.653805 0.309407 0.056 Uiso 1 1 calc R . . . .
C00I C 0.89756(17) 0.3138(2) 0.62449(16) 0.0507(6) Uani 1 1 d . . . . .
H00A H 0.936446 0.307880 0.576876 0.061 Uiso 1 1 calc R . . . .
H00B H 0.919406 0.241212 0.669415 0.061 Uiso 1 1 calc R . . . .
C13 C 0.59295(19) 0.2600(2) 0.51177(15) 0.0501(6) Uani 1 1 d . . . . .
H13 H 0.623788 0.205331 0.561526 0.060 Uiso 1 1 calc R . . . .
C16 C 0.50069(18) 0.4209(2) 0.36504(16) 0.0530(6) Uani 1 1 d . . . . .
H16 H 0.468243 0.473970 0.315058 0.064 Uiso 1 1 calc R . . . .
C22 C 0.69990(19) 0.7291(2) 0.29562(13) 0.0518(6) Uani 1 1 d . . . . .
H22A H 0.760483 0.692049 0.281239 0.062 Uiso 1 1 calc R . . . .
H22B H 0.676496 0.803320 0.252508 0.062 Uiso 1 1 calc R . . . .
C4 C 0.77470(18) 0.9453(2) 0.65372(16) 0.0524(6) Uani 1 1 d . . . . .
H4 H 0.751530 1.031867 0.665289 0.063 Uiso 1 1 calc R . . . .
C9 C 1.02038(19) 0.4661(2) 0.72534(16) 0.0554(6) Uani 1 1 d . . . . .
H9 H 1.069035 0.479173 0.690901 0.066 Uiso 1 1 calc R . . . .
C19 C 0.58225(19) 0.5891(3) 0.18327(16) 0.0605(7) Uani 1 1 d . . . . .
H19 H 0.558867 0.663544 0.145228 0.073 Uiso 1 1 calc R . . . .
C14 C 0.4903(2) 0.2655(3) 0.48801(17) 0.0601(7) Uani 1 1 d . . . . .
H14 H 0.452028 0.215133 0.521147 0.072 Uiso 1 1 calc R . . . .
C15 C 0.44507(19) 0.3471(3) 0.41396(17) 0.0612(7) Uani 1 1 d . . . . .
H15 H 0.375734 0.351672 0.397351 0.073 Uiso 1 1 calc R . . . .
C20 C 0.5786(2) 0.4715(3) 0.14456(19) 0.0803(9) Uani 1 1 d . . . . .
H20A H 0.601187 0.394201 0.180005 0.096 Uiso 1 1 calc R . . . .
H20B H 0.553295 0.463019 0.080894 0.096 Uiso 1 1 calc R . . . .
C10 C 1.0497(2) 0.4613(3) 0.81478(19) 0.0837(10) Uani 1 1 d . . . . .
H10A H 1.003429 0.448365 0.851751 0.100 Uiso 1 1 calc R . . . .
H10B H 1.117177 0.470744 0.842200 0.100 Uiso 1 1 calc R . . . .
H1 H 0.8938(15) 0.546(2) 0.5530(14) 0.035(6) Uiso 1 1 d . . . . .
H2 H 0.726(2) 0.489(3) 0.3550(16) 0.064(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.345(2) . ?
O1 C22 1.451(2) . ?
O3 C17 1.354(2) . ?
O3 C00I 1.446(2) . ?
O2 C7 1.214(2) . ?
O4 C17 1.206(2) . ?
N1 C1 1.366(3) . ?
N1 C21 1.446(3) . ?
N1 H1 0.80(2) . ?
N2 C11 1.368(3) . ?
N2 C18 1.454(3) . ?
N2 H2 0.90(3) . ?
C12 C11 1.418(3) . ?
C12 C17 1.471(3) . ?
C12 C13 1.395(3) . ?
C1 C2 1.413(3) . ?
C1 C6 1.399(3) . ?
C2 C7 1.468(3) . ?
C2 C3 1.394(3) . ?
C21 H21 0.9800 . ?
C21 C00I 1.517(3) . ?
C21 C9 1.502(3) . ?
C11 C16 1.401(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.372(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.366(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.380(3) . ?
C18 H18 0.9800 . ?
C18 C22 1.516(3) . ?
C18 C19 1.499(3) . ?
C00I H00A 0.9700 . ?
C00I H00B 0.9700 . ?
C13 H13 0.9300 . ?
C13 C14 1.376(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.362(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C4 H4 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.292(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.275(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(3) . ?
C15 H15 0.9300 . ?
C20 H20A 0.9300 . ?
C20 H20B 0.9300 . ?
C10 H10A 0.9300 . ?
C10 H10B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C22 117.38(17) . . ?
C17 O3 C00I 117.74(17) . . ?
C1 N1 C21 125.90(19) . . ?
C1 N1 H1 116.4(15) . . ?
C21 N1 H1 117.6(15) . . ?
C11 N2 C18 124.2(2) . . ?
C11 N2 H2 117.1(16) . . ?
C18 N2 H2 116.9(16) . . ?
C11 C12 C17 120.1(2) . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 C17 120.3(2) . . ?
N1 C1 C2 121.10(18) . . ?
N1 C1 C6 121.20(19) . . ?
C6 C1 C2 117.66(19) . . ?
C1 C2 C7 119.63(19) . . ?
C3 C2 C1 119.79(18) . . ?
C3 C2 C7 120.56(19) . . ?
N1 C21 H21 108.1 . . ?
N1 C21 C00I 109.29(17) . . ?
N1 C21 C9 112.48(19) . . ?
C00I C21 H21 108.1 . . ?
C9 C21 H21 108.1 . . ?
C9 C21 C00I 110.61(18) . . ?
N2 C11 C12 121.7(2) . . ?
N2 C11 C16 121.1(2) . . ?
C16 C11 C12 117.2(2) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.9(2) . . ?
C5 C6 H6 119.6 . . ?
O3 C17 C12 112.09(19) . . ?
O4 C17 O3 122.4(2) . . ?
O4 C17 C12 125.46(19) . . ?
O1 C7 C2 112.92(19) . . ?
O2 C7 O1 122.70(19) . . ?
O2 C7 C2 124.4(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C6 C5 H5 119.3 . . ?
C6 C5 C4 121.33(19) . . ?
C4 C5 H5 119.3 . . ?
N2 C18 H18 107.5 . . ?
N2 C18 C22 110.21(18) . . ?
N2 C18 C19 114.69(19) . . ?
C22 C18 H18 107.5 . . ?
C19 C18 H18 107.5 . . ?
C19 C18 C22 109.24(19) . . ?
O3 C00I C21 109.57(18) . . ?
O3 C00I H00A 109.8 . . ?
O3 C00I H00B 109.8 . . ?
C21 C00I H00A 109.8 . . ?
C21 C00I H00B 109.8 . . ?
H00A C00I H00B 108.2 . . ?
C12 C13 H13 119.2 . . ?
C14 C13 C12 121.6(2) . . ?
C14 C13 H13 119.2 . . ?
C11 C16 H16 119.0 . . ?
C15 C16 C11 122.0(2) . . ?
C15 C16 H16 119.0 . . ?
O1 C22 C18 109.97(17) . . ?
O1 C22 H22A 109.7 . . ?
O1 C22 H22B 109.7 . . ?
C18 C22 H22A 109.7 . . ?
C18 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C3 C4 C5 119.0(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C21 C9 H9 117.3 . . ?
C10 C9 C21 125.4(3) . . ?
C10 C9 H9 117.3 . . ?
C18 C19 H19 117.1 . . ?
C20 C19 C18 125.7(2) . . ?
C20 C19 H19 117.1 . . ?
C13 C14 H14 120.6 . . ?
C13 C14 C15 118.8(2) . . ?
C15 C14 H14 120.6 . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C19 C20 H20A 120.0 . . ?
C19 C20 H20B 120.0 . . ?
H20A C20 H20B 120.0 . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?

_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 1.217
_oxdiff_exptl_absorpt_empirical_full_min 0.906
####################################################################### 
# 
# 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_anti-3m
_database_code_depnum_ccdc_archive 'CCDC 1942742'
loop_
_audit_author_name
_audit_author_address
Fu
;HuaQiao University
China
;
_audit_update_record             
;
2019-11-04 deposited with the CCDC.	2019-12-06 downloaded from the CCDC.
;
_audit_creation_date             2019-11-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 F6 N2 O4'
_chemical_formula_sum            'C24 H20 F6 N2 O4'
_chemical_formula_weight         514.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H22N3O3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.1630(3)
_cell_length_b                   10.7505(3)
_cell_length_c                   10.3964(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.940(3)
_cell_angle_gamma                90
_cell_volume                     1135.22(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1608
_cell_measurement_temperature    293.1(2)
_cell_measurement_theta_max      70.7180
_cell_measurement_theta_min      4.3360
_shelx_estimated_absorpt_T_max   0.891
_shelx_estimated_absorpt_T_min   0.833
_exptl_absorpt_coefficient_mu    1.184
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4348
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.068
_diffrn_reflns_theta_max         67.068
_diffrn_reflns_theta_min         4.353
_diffrn_ambient_temperature      293.1(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -108.00  -38.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -30.0000 140

#__ type_ start__ end____ width___ exp.time_
  2 omega  -48.00   29.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000  150.0000 154

#__ type_ start__ end____ width___ exp.time_
  3 omega   66.00  106.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -30.0000 80

#__ type_ start__ end____ width___ exp.time_
  4 omega   58.00   95.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  150.0000 74

#__ type_ start__ end____ width___ exp.time_
  5 omega   44.00   75.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  120.0000 62

#__ type_ start__ end____ width___ exp.time_
  6 omega  -32.00   31.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000  -30.0000 126

#__ type_ start__ end____ width___ exp.time_
  7 omega   35.00   96.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -60.0000 122

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00   72.00   0.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 68

#__ type_ start__ end____ width___ exp.time_
  9 omega   65.00   91.00   0.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 52

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   63.00   0.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 50

#__ type_ start__ end____ width___ exp.time_
 11 omega  102.00  161.00   0.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 118

#__ type_ start__ end____ width___ exp.time_
 12 omega   91.00  160.00   0.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 138

#__ type_ start__ end____ width___ exp.time_
 13 omega   70.00  107.00   0.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 74

#__ type_ start__ end____ width___ exp.time_
 14 omega   56.00  126.00   0.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -150.0000 140

#__ type_ start__ end____ width___ exp.time_
 15 omega   99.00  173.00   0.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 148

#__ type_ start__ end____ width___ exp.time_
 16 omega   39.00  101.00   0.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 124

#__ type_ start__ end____ width___ exp.time_
 17 omega   38.00   85.00   0.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
 18 omega   39.00   80.00   0.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1420934000
_diffrn_orient_matrix_UB_12      -0.0030533000
_diffrn_orient_matrix_UB_13      0.0566327000
_diffrn_orient_matrix_UB_21      -0.0352486000
_diffrn_orient_matrix_UB_22      -0.1128473000
_diffrn_orient_matrix_UB_23      0.0833889000
_diffrn_orient_matrix_UB_31      0.0399403000
_diffrn_orient_matrix_UB_32      -0.0882739000
_diffrn_orient_matrix_UB_33      -0.1086255000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1663
_reflns_number_total             2029
_reflns_odcompleteness_completeness 99.95
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2029
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.088
_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)+(0.0792P)²+0.2074P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1455
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 F3A-C11
 1.37 with sigma of 0.02
 C11-F2A
 1.37 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F2A)
\\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F3A) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C8(H8)
5.b Secondary CH2 refined with riding coordinates:
 C0AA(H0AA,H0AB)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C3(H3), C9(H9)
5.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.75085(18) 0.44577(17) -0.04271(17) 0.0424(4) Uani 1 1 d . . . . .
C6 C 0.65078(19) 0.35582(19) -0.03767(19) 0.0479(4) Uani 1 1 d . . . . .
H6 H 0.632116 0.306166 -0.109233 0.057 Uiso 1 1 calc R . . . .
C5 C 0.58010(19) 0.34026(19) 0.0717(2) 0.0495(5) Uani 1 1 d . . . . .
C4 C 0.6057(2) 0.4108(2) 0.18141(19) 0.0534(5) Uani 1 1 d . . . . .
H4 H 0.555766 0.400846 0.254048 0.064 Uiso 1 1 calc R . . . .
C3 C 0.7066(2) 0.49580(19) 0.18008(19) 0.0502(5) Uani 1 1 d . . . . .
H3 H 0.726108 0.542226 0.253766 0.060 Uiso 1 1 calc R . . . .
C2 C 0.78070(18) 0.51430(16) 0.07085(17) 0.0429(4) Uani 1 1 d . . . . .
C7 C 0.89110(19) 0.60414(17) 0.07564(17) 0.0445(4) Uani 1 1 d . . . . .
C0AA C 1.0469(2) 0.70825(19) 0.2145(2) 0.0546(5) Uani 1 1 d . . . . .
H0AA H 1.033942 0.769888 0.281044 0.065 Uiso 1 1 calc R . . . .
H0AB H 1.065394 0.751520 0.135277 0.065 Uiso 1 1 calc R . . . .
C8 C 0.8380(2) 0.37537(19) -0.25307(18) 0.0503(5) Uani 1 1 d . . . . .
H8 H 0.759244 0.323023 -0.262029 0.060 Uiso 1 1 calc R . . . .
C9 C 0.8586(2) 0.4365(2) -0.3811(2) 0.0626(6) Uani 1 1 d . . . . .
H9 H 0.896203 0.387565 -0.443857 0.075 Uiso 1 1 calc R . . . .
C10 C 0.8296(3) 0.5499(3) -0.4131(3) 0.0764(7) Uani 1 1 d . . . . .
H10A H 0.791814 0.602739 -0.353902 0.092 Uiso 1 1 calc R . . . .
H10B H 0.846561 0.578545 -0.495337 0.092 Uiso 1 1 calc R . . . .
C11 C 0.4752(2) 0.2425(2) 0.0722(2) 0.0610(6) Uani 1 1 d D . . . .
F1 F 0.4379(10) 0.2019(12) -0.0428(5) 0.132(3) Uani 0.610(19) 1 d . U P A 1
F1A F 0.5144(14) 0.1333(11) 0.083(2) 0.123(5) Uani 0.390(19) 1 d . U P A 2
F2 F 0.5157(8) 0.1441(8) 0.1411(10) 0.099(2) Uani 0.610(19) 1 d . U P A 1
F2A F 0.3893(17) 0.2591(17) 0.1601(19) 0.149(5) Uani 0.390(19) 1 d D U P A 2
F3 F 0.3675(4) 0.2784(6) 0.1284(7) 0.0873(17) Uani 0.610(19) 1 d . U P A 1
F3A F 0.4066(10) 0.2407(11) -0.0339(11) 0.107(4) Uani 0.390(19) 1 d D U P A 2
N1 N 0.81369(17) 0.46846(16) -0.15508(15) 0.0481(4) Uani 1 1 d . . . . .
O2 O 0.94414(15) 0.64567(13) -0.01820(13) 0.0538(4) Uani 1 1 d . . . . .
O1 O 0.92928(14) 0.63398(14) 0.19651(13) 0.0523(4) Uani 1 1 d . . . . .
H1 H 0.877(3) 0.529(3) -0.148(2) 0.058(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.406(3) . ?
C1 C2 1.416(3) . ?
C1 N1 1.372(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.376(3) . ?
C5 C4 1.387(3) . ?
C5 C11 1.497(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.374(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.398(3) . ?
C2 C7 1.480(3) . ?
C7 O2 1.215(2) . ?
C7 O1 1.342(2) . ?
C0AA H0AA 0.9700 . ?
C0AA H0AB 0.9700 . ?
C0AA C8 1.519(3) 3_765 ?
C0AA O1 1.444(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.505(3) . ?
C8 N1 1.455(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.296(4) . ?
C10 H10A 0.9300 . ?
C10 H10B 0.9300 . ?
C11 F1 1.317(6) . ?
C11 F1A 1.244(12) . ?
C11 F2 1.336(8) . ?
C11 F2A 1.298(11) . ?
C11 F3 1.316(5) . ?
C11 F3A 1.284(9) . ?
N1 H1 0.92(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 117.50(16) . . ?
N1 C1 C6 120.81(17) . . ?
N1 C1 C2 121.65(17) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.88(19) . . ?
C5 C6 H6 119.6 . . ?
C6 C5 C4 121.65(19) . . ?
C6 C5 C11 118.7(2) . . ?
C4 C5 C11 119.66(19) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 C5 118.33(17) . . ?
C3 C4 H4 120.8 . . ?
C4 C3 H3 119.1 . . ?
C4 C3 C2 121.71(19) . . ?
C2 C3 H3 119.1 . . ?
C1 C2 C7 120.56(16) . . ?
C3 C2 C1 119.82(18) . . ?
C3 C2 C7 119.62(17) . . ?
O2 C7 C2 124.68(17) . . ?
O2 C7 O1 122.82(18) . . ?
O1 C7 C2 112.49(16) . . ?
H0AA C0AA H0AB 108.2 . . ?
C8 C0AA H0AA 109.8 3_765 . ?
C8 C0AA H0AB 109.8 3_765 . ?
O1 C0AA H0AA 109.8 . . ?
O1 C0AA H0AB 109.8 . . ?
O1 C0AA C8 109.50(16) . 3_765 ?
C0AA C8 H8 107.7 3_765 . ?
C9 C8 C0AA 111.24(18) . 3_765 ?
C9 C8 H8 107.7 . . ?
N1 C8 C0AA 111.70(16) . 3_765 ?
N1 C8 H8 107.7 . . ?
N1 C8 C9 110.55(18) . . ?
C8 C9 H9 116.5 . . ?
C10 C9 C8 126.9(2) . . ?
C10 C9 H9 116.5 . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
F1 C11 C5 114.4(3) . . ?
F1 C11 F2 107.4(5) . . ?
F1A C11 C5 115.9(7) . . ?
F1A C11 F2A 106.6(9) . . ?
F1A C11 F3A 103.2(9) . . ?
F2 C11 C5 110.6(4) . . ?
F2A C11 C5 113.7(7) . . ?
F3 C11 C5 113.5(4) . . ?
F3 C11 F1 106.4(5) . . ?
F3 C11 F2 103.9(5) . . ?
F3A C11 C5 112.0(5) . . ?
F3A C11 F2A 104.4(9) . . ?
C1 N1 C8 124.66(16) . . ?
C1 N1 H1 114.0(16) . . ?
C8 N1 H1 114.0(16) . . ?
C7 O1 C0AA 117.74(15) . . ?

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
C1 C6 C5 C4 -1.0(3) . . . . ?
C1 C6 C5 C11 -179.62(18) . . . . ?
C1 C2 C7 O2 16.4(3) . . . . ?
C1 C2 C7 O1 -162.35(16) . . . . ?
C6 C1 C2 C3 -3.5(3) . . . . ?
C6 C1 C2 C7 175.62(16) . . . . ?
C6 C1 N1 C8 -32.1(3) . . . . ?
C6 C5 C4 C3 -1.6(3) . . . . ?
C6 C5 C11 F1 -16.4(8) . . . . ?
C6 C5 C11 F1A 75.9(13) . . . . ?
C6 C5 C11 F2 104.9(5) . . . . ?
C6 C5 C11 F2A -160.1(13) . . . . ?
C6 C5 C11 F3 -138.8(4) . . . . ?
C6 C5 C11 F3A -42.1(7) . . . . ?
C5 C4 C3 C2 1.6(3) . . . . ?
C4 C5 C11 F1 164.9(7) . . . . ?
C4 C5 C11 F1A -102.8(13) . . . . ?
C4 C5 C11 F2 -73.7(6) . . . . ?
C4 C5 C11 F2A 21.2(13) . . . . ?
C4 C5 C11 F3 42.5(4) . . . . ?
C4 C5 C11 F3A 139.2(7) . . . . ?
C4 C3 C2 C1 1.0(3) . . . . ?
C4 C3 C2 C7 -178.09(18) . . . . ?
C3 C2 C7 O2 -164.49(19) . . . . ?
C3 C2 C7 O1 16.7(2) . . . . ?
C2 C1 C6 C5 3.5(3) . . . . ?
C2 C1 N1 C8 150.04(19) . . . . ?
C2 C7 O1 C0AA 172.20(16) . . . . ?
C0AA C8 C9 C10 -140.4(3) 3_765 . . . ?
C0AA C8 N1 C1 -77.6(2) 3_765 . . . ?
C8 C0AA O1 C7 -100.08(19) 3_765 . . . ?
C9 C8 N1 C1 157.91(18) . . . . ?
C11 C5 C4 C3 177.03(19) . . . . ?
N1 C1 C6 C5 -174.46(18) . . . . ?
N1 C1 C2 C3 174.44(18) . . . . ?
N1 C1 C2 C7 -6.5(3) . . . . ?
N1 C8 C9 C10 -15.7(3) . . . . ?
O2 C7 O1 C0AA -6.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_syn-3l
_database_code_depnum_ccdc_archive 'CCDC 1942741'
loop_
_audit_author_name
_audit_author_address
Fu
;HuaQiao University
China
;
_audit_update_record             
;
2019-11-04 deposited with the CCDC.	2019-12-06 downloaded from the CCDC.
;
_audit_creation_date             2019-11-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 F2 N2 O4'
_chemical_formula_sum            'C22 H20 F2 N2 O4'
_chemical_formula_weight         414.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.6617(14)
_cell_length_b                   9.8335(5)
_cell_length_c                   12.6100(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.347(7)
_cell_angle_gamma                90
_cell_volume                     1992.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1967
_cell_measurement_temperature    293.1(2)
_cell_measurement_theta_max      24.9560
_cell_measurement_theta_min      4.1910
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9755
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.262
_diffrn_reflns_theta_min         3.628
_diffrn_ambient_temperature      293.1(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  83.00   1.00    7.50    --   15.49  57.00  30.00   82
  2  ω     35.00  60.00   1.00    7.50    --   15.49 178.00-180.00   25
  3  ω    -49.00  42.00   1.00    7.50    --   15.49 -77.00-120.00   91
  4  ω    -19.00   8.00   1.00    7.50    --  -16.12 -99.00  30.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0406586000
_diffrn_orient_matrix_UB_12      -0.0037742000
_diffrn_orient_matrix_UB_13      -0.0360731000
_diffrn_orient_matrix_UB_21      0.0068030000
_diffrn_orient_matrix_UB_22      -0.0692290000
_diffrn_orient_matrix_UB_23      -0.0108836000
_diffrn_orient_matrix_UB_31      -0.0158879000
_diffrn_orient_matrix_UB_32      -0.0199847000
_diffrn_orient_matrix_UB_33      0.0444779000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2577
_reflns_number_total             4601
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4601
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.1145
_refine_ls_R_factor_gt           0.0609
_refine_ls_restrained_S_all      1.050
_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)+(0.0670P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1623
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C9-C8 \\sim C9B-C8
 with sigma of 0.01
 C9B-C10B \\sim C9-C10
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C9) \\sim Ueq, Uanis(C9B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C10) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(H8B)=Sof(C10B)=Sof(H10C)=Sof(H10D)=Sof(C9B)=Sof(H9B)=1-FVAR(1)
 Sof(H8A)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10A)=Sof(H10B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C8(H8A), C8(H8B), C18(H18)
5.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C3(H3), C9(H9), C16(H16), C14(H14), C13(H13), C19(H19),
 C9B(H9B)
5.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B), C20(H20A,H20B), C10B(H10C,H10D)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.49630(10) 0.90246(15) 0.60415(13) 0.0765(5) Uani 1 1 d . . . . .
F2 F 0.05091(10) 0.33548(14) 0.14034(11) 0.0715(5) Uani 1 1 d . . . . .
O2 O 0.32640(11) 0.36684(15) 0.73266(13) 0.0545(5) Uani 1 1 d . . . . .
O1 O 0.38474(11) 0.30960(15) 0.59671(13) 0.0558(5) Uani 1 1 d . . . . .
O4 O 0.15646(10) 0.44289(15) 0.65468(12) 0.0503(4) Uani 1 1 d . . . . .
O3 O 0.12218(10) 0.64884(14) 0.57969(12) 0.0520(4) Uani 1 1 d . . . . .
N1 N 0.29464(14) 0.6463(2) 0.71990(16) 0.0492(5) Uani 1 1 d . . . . .
N2 N 0.20674(13) 0.27563(19) 0.51038(17) 0.0484(5) Uani 1 1 d . . . . .
C1 C 0.36569(15) 0.6510(2) 0.68545(17) 0.0444(6) Uani 1 1 d . . . . .
C6 C 0.39915(16) 0.7759(2) 0.66508(18) 0.0497(6) Uani 1 1 d . . . . .
H6 H 0.374142 0.856738 0.677561 0.060 Uiso 1 1 calc R . . . .
C5 C 0.46814(17) 0.7788(2) 0.6271(2) 0.0551(7) Uani 1 1 d . . . . .
C4 C 0.51066(17) 0.6651(3) 0.6098(2) 0.0627(7) Uani 1 1 d . . . . .
H4 H 0.559190 0.671082 0.586867 0.075 Uiso 1 1 calc R . . . .
C3 C 0.47779(16) 0.5418(3) 0.62819(19) 0.0562(6) Uani 1 1 d . . . . .
H3 H 0.504587 0.462543 0.616290 0.067 Uiso 1 1 calc R . . . .
C2 C 0.40607(14) 0.5314(2) 0.66386(16) 0.0438(5) Uani 1 1 d . . . . .
C7 C 0.36847(15) 0.3973(2) 0.67171(18) 0.0471(6) Uani 1 1 d . . . . .
C8 C 0.23733(16) 0.7598(2) 0.7103(2) 0.0502(6) Uani 1 1 d D . . . .
H8A H 0.240932 0.811631 0.645325 0.060 Uiso 0.725(8) 1 calc R . P A 1
H8B H 0.243223 0.822202 0.652215 0.060 Uiso 0.275(8) 1 calc R . P A 2
C21 C 0.14845(17) 0.7093(2) 0.6875(2) 0.0573(7) Uani 1 1 d . . . . .
H21A H 0.144484 0.642501 0.742499 0.069 Uiso 1 1 calc R . . . .
H21B H 0.111981 0.784609 0.692237 0.069 Uiso 1 1 calc R . . . .
C9 C 0.2512(4) 0.8594(7) 0.8035(5) 0.067(2) Uani 0.725(8) 1 d D U P A 1
H9 H 0.215009 0.932529 0.798602 0.080 Uiso 0.725(8) 1 calc R . P A 1
C10 C 0.3120(3) 0.8457(6) 0.8898(4) 0.0834(19) Uani 0.725(8) 1 d D U P A 1
H10A H 0.348490 0.772857 0.895499 0.100 Uiso 0.725(8) 1 calc R . P A 1
H10B H 0.319503 0.908497 0.946725 0.100 Uiso 0.725(8) 1 calc R . P A 1
C11 C 0.14922(14) 0.3454(2) 0.43247(17) 0.0408(5) Uani 1 1 d . . . . .
C16 C 0.12812(15) 0.3048(2) 0.32208(17) 0.0478(6) Uani 1 1 d . . . . .
H16 H 0.152700 0.228468 0.300400 0.057 Uiso 1 1 calc R . . . .
C15 C 0.07090(16) 0.3790(2) 0.24688(18) 0.0491(6) Uani 1 1 d . . . . .
C14 C 0.03138(15) 0.4918(2) 0.27065(19) 0.0522(6) Uani 1 1 d . . . . .
H14 H -0.008244 0.537709 0.216690 0.063 Uiso 1 1 calc R . . . .
C13 C 0.05300(14) 0.5343(2) 0.37828(19) 0.0477(6) Uani 1 1 d . . . . .
H13 H 0.028728 0.612714 0.397007 0.057 Uiso 1 1 calc R . . . .
C12 C 0.11002(13) 0.4635(2) 0.45995(17) 0.0403(5) Uani 1 1 d . . . . .
C18 C 0.26622(16) 0.1805(2) 0.48829(19) 0.0499(6) Uani 1 1 d . . . . .
H18 H 0.282077 0.211949 0.422915 0.060 Uiso 1 1 calc R . . . .
C22 C 0.34426(16) 0.1790(2) 0.5846(2) 0.0568(7) Uani 1 1 d . . . . .
H22A H 0.329244 0.156257 0.651694 0.068 Uiso 1 1 calc R . . . .
H22B H 0.382320 0.109861 0.572145 0.068 Uiso 1 1 calc R . . . .
C19 C 0.2340(2) 0.0375(2) 0.4672(2) 0.0620(8) Uani 1 1 d . . . . .
H19 H 0.268322 -0.025357 0.445706 0.074 Uiso 1 1 calc R . . . .
C20 C 0.1627(2) -0.0062(3) 0.4763(2) 0.0735(9) Uani 1 1 d . . . . .
H20A H 0.126321 0.053143 0.497648 0.088 Uiso 1 1 calc R . . . .
H20B H 0.147854 -0.096755 0.461580 0.088 Uiso 1 1 calc R . . . .
C17 C 0.13151(14) 0.5134(2) 0.57378(19) 0.0425(5) Uani 1 1 d . . . . .
C10B C 0.2847(7) 0.9521(11) 0.8481(11) 0.073(4) Uani 0.275(8) 1 d D . P A 2
H10C H 0.275171 1.017599 0.792895 0.087 Uiso 0.275(8) 1 calc R . P A 2
H10D H 0.304855 0.977825 0.921280 0.087 Uiso 0.275(8) 1 calc R . P A 2
H2 H 0.2126(13) 0.300(2) 0.5761(18) 0.039(6) Uiso 1 1 d . . . . .
H1 H 0.2776(15) 0.568(2) 0.7303(17) 0.049(7) Uiso 1 1 d . . . . .
C9B C 0.2700(14) 0.8255(14) 0.8230(10) 0.063(6) Uani 0.275(8) 1 d D U P A 2
H9B H 0.281001 0.765753 0.882244 0.075 Uiso 0.275(8) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C5 1.361(3) . ?
F2 C15 1.364(3) . ?
O2 C7 1.207(3) . ?
O1 C7 1.359(3) . ?
O1 C22 1.440(3) . ?
O4 C17 1.212(2) . ?
O3 C21 1.441(3) . ?
O3 C17 1.346(2) . ?
N1 C1 1.365(3) . ?
N1 C8 1.453(3) . ?
N1 H1 0.84(2) . ?
N2 C11 1.362(3) . ?
N2 C18 1.443(3) . ?
N2 H2 0.84(2) . ?
C1 C6 1.401(3) . ?
C1 C2 1.416(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.358(3) . ?
C5 C4 1.372(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.375(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.388(3) . ?
C2 C7 1.475(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 C21 1.516(4) . ?
C8 C9 1.500(5) . ?
C8 C9B 1.524(9) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C9 H9 0.9300 . ?
C9 C10 1.282(7) . ?
C10 H10A 0.9300 . ?
C10 H10B 0.9300 . ?
C11 C16 1.401(3) . ?
C11 C12 1.420(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.365(3) . ?
C15 C14 1.363(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.374(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.389(3) . ?
C12 C17 1.469(3) . ?
C18 H18 0.9800 . ?
C18 C22 1.526(4) . ?
C18 C19 1.504(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C19 H19 0.9300 . ?
C19 C20 1.297(4) . ?
C20 H20A 0.9300 . ?
C20 H20B 0.9300 . ?
C10B H10C 0.9300 . ?
C10B H10D 0.9300 . ?
C10B C9B 1.292(10) . ?
C9B H9B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C22 117.77(19) . . ?
C17 O3 C21 116.72(17) . . ?
C1 N1 C8 123.6(2) . . ?
C1 N1 H1 116.0(17) . . ?
C8 N1 H1 118.2(17) . . ?
C11 N2 C18 125.1(2) . . ?
C11 N2 H2 116.1(14) . . ?
C18 N2 H2 118.0(15) . . ?
N1 C1 C6 120.6(2) . . ?
N1 C1 C2 121.9(2) . . ?
C6 C1 C2 117.4(2) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 119.9(2) . . ?
C5 C6 H6 120.0 . . ?
F1 C5 C4 118.2(3) . . ?
C6 C5 F1 117.7(2) . . ?
C6 C5 C4 124.0(2) . . ?
C5 C4 H4 121.7 . . ?
C5 C4 C3 116.5(3) . . ?
C3 C4 H4 121.7 . . ?
C4 C3 H3 118.8 . . ?
C4 C3 C2 122.3(2) . . ?
C2 C3 H3 118.8 . . ?
C1 C2 C7 119.8(2) . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 C7 120.3(2) . . ?
O2 C7 O1 122.8(2) . . ?
O2 C7 C2 126.4(2) . . ?
O1 C7 C2 110.8(2) . . ?
N1 C8 H8A 106.6 . . ?
N1 C8 H8B 110.5 . . ?
N1 C8 C21 110.57(19) . . ?
N1 C8 C9 118.3(3) . . ?
N1 C8 C9B 100.5(7) . . ?
C21 C8 H8A 106.6 . . ?
C21 C8 H8B 110.5 . . ?
C21 C8 C9B 114.0(9) . . ?
C9 C8 H8A 106.6 . . ?
C9 C8 C21 107.6(4) . . ?
C9B C8 H8B 110.5 . . ?
O3 C21 C8 110.6(2) . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
C8 C21 H21A 109.5 . . ?
C8 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.3(6) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
N2 C11 C16 121.1(2) . . ?
N2 C11 C12 121.2(2) . . ?
C16 C11 C12 117.7(2) . . ?
C11 C16 H16 120.5 . . ?
C15 C16 C11 118.9(2) . . ?
C15 C16 H16 120.5 . . ?
F2 C15 C16 117.4(2) . . ?
C14 C15 F2 117.7(2) . . ?
C14 C15 C16 124.9(2) . . ?
C15 C14 H14 121.7 . . ?
C15 C14 C13 116.7(2) . . ?
C13 C14 H14 121.7 . . ?
C14 C13 H13 119.0 . . ?
C14 C13 C12 122.0(2) . . ?
C12 C13 H13 119.0 . . ?
C11 C12 C17 120.17(19) . . ?
C13 C12 C11 119.82(19) . . ?
C13 C12 C17 119.98(19) . . ?
N2 C18 H18 108.0 . . ?
N2 C18 C22 109.70(19) . . ?
N2 C18 C19 114.2(2) . . ?
C22 C18 H18 108.0 . . ?
C19 C18 H18 108.0 . . ?
C19 C18 C22 108.69(19) . . ?
O1 C22 C18 110.62(18) . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
C18 C19 H19 117.0 . . ?
C20 C19 C18 125.9(3) . . ?
C20 C19 H19 117.0 . . ?
C19 C20 H20A 120.0 . . ?
C19 C20 H20B 120.0 . . ?
H20A C20 H20B 120.0 . . ?
O4 C17 O3 122.57(19) . . ?
O4 C17 C12 124.93(19) . . ?
O3 C17 C12 112.49(19) . . ?
H10C C10B H10D 120.0 . . ?
C9B C10B H10C 120.0 . . ?
C9B C10B H10D 120.0 . . ?
C8 C9B H9B 115.3 . . ?
C10B C9B C8 129.4(13) . . ?
C10B C9B H9B 115.3 . . ?

_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 3.038
_oxdiff_exptl_absorpt_empirical_full_min 0.652
####################################################################### 
# 
# 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_syn-3g
_database_code_depnum_ccdc_archive 'CCDC 1942740'
loop_
_audit_author_name
_audit_author_address
Fu
;HuaQiao University
China
;
_audit_update_record             
;
2019-11-04 deposited with the CCDC.	2019-12-06 downloaded from the CCDC.
;
_audit_creation_date             2019-11-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H26 N2 O6'
_chemical_formula_sum            'C24 H26 N2 O6'
_chemical_formula_weight         438.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   11.5668(5)
_cell_length_b                   17.1785(9)
_cell_length_c                   23.0513(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4580.3(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4025
_cell_measurement_temperature    293.1(2)
_cell_measurement_theta_max      24.7610
_cell_measurement_theta_min      3.7180
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            25391
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.492
_diffrn_reflns_theta_min         3.443
_diffrn_ambient_temperature      293.1(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  83.00   0.80    5.00    --   15.49  57.00 -60.00  100
  2  ω     37.00  72.20   0.80    5.00    --   15.49 178.00   0.00   44
  3  ω    -21.00  22.20   0.80    5.00    --  -16.28 -99.00 120.00   54
  4  ω     56.00  80.80   0.80    5.00    --   15.49-147.00  71.00   31
  5  ω     -2.00  50.00   0.80    5.00    --   15.49-124.00-123.00   65
  6  ω    -21.00   9.40   0.80    5.00    --  -16.28 -99.00-120.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0224015000
_diffrn_orient_matrix_UB_12      -0.0382268000
_diffrn_orient_matrix_UB_13      0.0032334000
_diffrn_orient_matrix_UB_21      -0.0024509000
_diffrn_orient_matrix_UB_22      -0.0052846000
_diffrn_orient_matrix_UB_23      -0.0304831000
_diffrn_orient_matrix_UB_31      0.0569943000
_diffrn_orient_matrix_UB_32      0.0147763000
_diffrn_orient_matrix_UB_33      -0.0025919000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3156
_reflns_number_total             5572
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5572
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0608
_refine_ls_restrained_S_all      1.069
_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)+(0.0680P)²+0.9273P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1341
_refine_ls_wR_factor_ref         0.1672
_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. Uiso/Uaniso restraints and constraints
Uanis(C23) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C8(H8), C18(H18)
3.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C9(H9), C13(H13), C15(H15), C16(H16), C19(H19)
3.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B), C20(H20A,H20B)
3.e Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.79532(12) 0.68355(9) 0.56850(6) 0.0515(4) Uani 1 1 d . . . . .
O2 O 0.69039(14) 0.59392(10) 0.52070(6) 0.0576(4) Uani 1 1 d . . . . .
O3 O 0.37489(12) 0.57072(8) 0.62652(6) 0.0475(4) Uani 1 1 d . . . . .
O4 O 0.44398(12) 0.61575(9) 0.54163(6) 0.0492(4) Uani 1 1 d . . . . .
O5 O 0.99508(15) 0.52912(11) 0.72583(8) 0.0704(5) Uani 1 1 d . . . . .
O6 O 0.28853(19) 0.80512(12) 0.74637(8) 0.0874(7) Uani 1 1 d . . . . .
N1 N 0.58946(15) 0.49057(12) 0.59877(8) 0.0472(5) Uani 1 1 d . . . . .
N2 N 0.56561(16) 0.75333(13) 0.55295(8) 0.0505(5) Uani 1 1 d . . . . .
C1 C 0.69124(16) 0.50232(12) 0.62809(8) 0.0383(5) Uani 1 1 d . . . . .
C2 C 0.77136(17) 0.56080(12) 0.61261(8) 0.0394(5) Uani 1 1 d . . . . .
C3 C 0.87307(17) 0.57169(12) 0.64507(9) 0.0460(5) Uani 1 1 d . . . . .
H3 H 0.924933 0.610598 0.634597 0.055 Uiso 1 1 calc R . . . .
C4 C 0.89637(18) 0.52498(13) 0.69236(9) 0.0478(5) Uani 1 1 d . . . . .
C5 C 0.81828(19) 0.46788(13) 0.70765(9) 0.0502(6) Uani 1 1 d . . . . .
H5 H 0.833656 0.436458 0.739588 0.060 Uiso 1 1 calc R . . . .
C6 C 0.71891(18) 0.45654(13) 0.67687(9) 0.0470(5) Uani 1 1 d . . . . .
H6 H 0.668085 0.417554 0.688399 0.056 Uiso 1 1 calc R . . . .
C7 C 0.74820(17) 0.61211(13) 0.56250(9) 0.0430(5) Uani 1 1 d . . . . .
C8 C 0.48962(17) 0.45113(12) 0.62340(9) 0.0443(5) Uani 1 1 d . . . . .
H8 H 0.494860 0.453907 0.665780 0.053 Uiso 1 1 calc R . . . .
C9 C 0.4841(2) 0.36671(14) 0.60581(11) 0.0564(6) Uani 1 1 d . . . . .
H9 H 0.490788 0.355576 0.566471 0.068 Uiso 1 1 calc R . . . .
C10 C 0.4712(3) 0.30917(19) 0.64024(16) 0.1043(11) Uani 1 1 d . . . . .
H10A H 0.464203 0.317683 0.679927 0.125 Uiso 1 1 calc R . . . .
H10B H 0.468733 0.258730 0.625634 0.125 Uiso 1 1 calc R . . . .
C11 C 0.49212(17) 0.76378(13) 0.59949(9) 0.0430(5) Uani 1 1 d . . . . .
C12 C 0.41880(16) 0.70394(12) 0.62028(8) 0.0406(5) Uani 1 1 d . . . . .
C13 C 0.35087(18) 0.71676(13) 0.66987(9) 0.0496(5) Uani 1 1 d . . . . .
H13 H 0.304248 0.676924 0.683982 0.059 Uiso 1 1 calc R . . . .
C14 C 0.3524(2) 0.78753(14) 0.69784(10) 0.0577(6) Uani 1 1 d . . . . .
C15 C 0.4217(2) 0.84687(14) 0.67657(11) 0.0632(7) Uani 1 1 d . . . . .
H15 H 0.422001 0.895007 0.695031 0.076 Uiso 1 1 calc R . . . .
C16 C 0.4898(2) 0.83551(14) 0.62876(10) 0.0543(6) Uani 1 1 d . . . . .
H16 H 0.535510 0.876217 0.615321 0.065 Uiso 1 1 calc R . . . .
C17 C 0.41440(16) 0.62764(12) 0.59155(9) 0.0390(5) Uani 1 1 d . . . . .
C18 C 0.67378(18) 0.79597(13) 0.54700(10) 0.0497(6) Uani 1 1 d . . . . .
H18 H 0.696748 0.812513 0.586022 0.060 Uiso 1 1 calc R . . . .
C19 C 0.6673(2) 0.86826(16) 0.51013(12) 0.0705(8) Uani 1 1 d . . . . .
H19 H 0.734278 0.898032 0.507704 0.085 Uiso 1 1 calc R . . . .
C20 C 0.5815(3) 0.8926(2) 0.48239(16) 0.1085(12) Uani 1 1 d . . . . .
H20A H 0.512284 0.865038 0.483324 0.130 Uiso 1 1 calc R . . . .
H20B H 0.586913 0.938243 0.460861 0.130 Uiso 1 1 calc R . . . .
C21 C 0.37835(18) 0.49162(12) 0.60428(10) 0.0479(5) Uani 1 1 d . . . . .
H21A H 0.374420 0.492579 0.562250 0.057 Uiso 1 1 calc R . . . .
H21B H 0.312093 0.462824 0.618582 0.057 Uiso 1 1 calc R . . . .
C22 C 0.76817(19) 0.74184(14) 0.52472(10) 0.0550(6) Uani 1 1 d . . . . .
H22A H 0.742307 0.716368 0.489479 0.066 Uiso 1 1 calc R . . . .
H22B H 0.836949 0.771775 0.515669 0.066 Uiso 1 1 calc R . . . .
C23 C 1.0734(3) 0.5879(2) 0.7146(2) 0.1386(18) Uani 1 1 d . U . . .
H23A H 1.111009 0.578221 0.678238 0.208 Uiso 1 1 calc GR . . . .
H23B H 1.130052 0.589599 0.745035 0.208 Uiso 1 1 calc GR . . . .
H23C H 1.033456 0.636880 0.712876 0.208 Uiso 1 1 calc GR . . . .
C24 C 0.2329(3) 0.74595(19) 0.77609(13) 0.0905(10) Uani 1 1 d . . . . .
H24A H 0.171946 0.725159 0.752434 0.136 Uiso 1 1 calc GR . . . .
H24B H 0.200844 0.766184 0.811427 0.136 Uiso 1 1 calc GR . . . .
H24C H 0.287254 0.705462 0.785020 0.136 Uiso 1 1 calc GR . . . .
H2 H 0.560(2) 0.7097(15) 0.5364(10) 0.053(7) Uiso 1 1 d . . . . .
H1 H 0.5818(18) 0.5158(14) 0.5686(10) 0.051(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.350(3) . ?
O1 C22 1.456(2) . ?
O2 C7 1.214(2) . ?
O3 C17 1.347(2) . ?
O3 C21 1.453(2) . ?
O4 C17 1.218(2) . ?
O5 C4 1.380(2) . ?
O5 C23 1.381(4) . ?
O6 C14 1.374(3) . ?
O6 C24 1.385(3) . ?
N1 C1 1.373(3) . ?
N1 C8 1.454(3) . ?
N1 H1 0.82(2) . ?
N2 C11 1.380(3) . ?
N2 C18 1.456(3) . ?
N2 H2 0.84(2) . ?
C1 C2 1.413(3) . ?
C1 C6 1.409(3) . ?
C2 C3 1.407(3) . ?
C2 C7 1.477(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(3) . ?
C4 C5 1.379(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.365(3) . ?
C6 H6 0.9300 . ?
C8 H8 0.9800 . ?
C8 C9 1.507(3) . ?
C8 C21 1.528(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.276(4) . ?
C10 H10A 0.9300 . ?
C10 H10B 0.9300 . ?
C11 C12 1.416(3) . ?
C11 C16 1.405(3) . ?
C12 C13 1.404(3) . ?
C12 C17 1.470(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(3) . ?
C14 C15 1.387(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.368(3) . ?
C16 H16 0.9300 . ?
C18 H18 0.9800 . ?
C18 C19 1.507(3) . ?
C18 C22 1.523(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.253(4) . ?
C20 H20A 0.9300 . ?
C20 H20B 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C22 117.85(17) . . ?
C17 O3 C21 117.28(16) . . ?
C4 O5 C23 118.4(2) . . ?
C14 O6 C24 119.4(2) . . ?
C1 N1 C8 123.87(18) . . ?
C1 N1 H1 115.5(16) . . ?
C8 N1 H1 119.3(16) . . ?
C11 N2 C18 122.5(2) . . ?
C11 N2 H2 114.6(16) . . ?
C18 N2 H2 118.3(16) . . ?
N1 C1 C2 122.88(18) . . ?
N1 C1 C6 120.39(19) . . ?
C6 C1 C2 116.72(18) . . ?
C1 C2 C7 120.19(18) . . ?
C3 C2 C1 120.58(18) . . ?
C3 C2 C7 119.22(18) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
O5 C4 C3 125.0(2) . . ?
C5 C4 O5 115.82(19) . . ?
C5 C4 C3 119.2(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 119.1 . . ?
C5 C6 C1 121.8(2) . . ?
C5 C6 H6 119.1 . . ?
O1 C7 C2 112.90(17) . . ?
O2 C7 O1 122.53(19) . . ?
O2 C7 C2 124.5(2) . . ?
N1 C8 H8 108.5 . . ?
N1 C8 C9 112.12(18) . . ?
N1 C8 C21 110.13(18) . . ?
C9 C8 H8 108.5 . . ?
C9 C8 C21 108.97(18) . . ?
C21 C8 H8 108.5 . . ?
C8 C9 H9 117.2 . . ?
C10 C9 C8 125.7(3) . . ?
C10 C9 H9 117.2 . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
N2 C11 C12 122.5(2) . . ?
N2 C11 C16 119.9(2) . . ?
C16 C11 C12 117.54(19) . . ?
C11 C12 C17 121.04(18) . . ?
C13 C12 C11 119.78(19) . . ?
C13 C12 C17 119.16(19) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
O6 C14 C13 124.6(2) . . ?
O6 C14 C15 115.9(2) . . ?
C13 C14 C15 119.4(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.8(2) . . ?
C16 C15 H15 119.6 . . ?
C11 C16 H16 119.2 . . ?
C15 C16 C11 121.5(2) . . ?
C15 C16 H16 119.2 . . ?
O3 C17 C12 112.92(17) . . ?
O4 C17 O3 122.61(19) . . ?
O4 C17 C12 124.46(19) . . ?
N2 C18 H18 107.0 . . ?
N2 C18 C19 115.1(2) . . ?
N2 C18 C22 109.91(19) . . ?
C19 C18 H18 107.0 . . ?
C19 C18 C22 110.40(19) . . ?
C22 C18 H18 107.0 . . ?
C18 C19 H19 116.5 . . ?
C20 C19 C18 127.0(3) . . ?
C20 C19 H19 116.5 . . ?
C19 C20 H20A 120.0 . . ?
C19 C20 H20B 120.0 . . ?
H20A C20 H20B 120.0 . . ?
O3 C21 C8 110.32(16) . . ?
O3 C21 H21A 109.6 . . ?
O3 C21 H21B 109.6 . . ?
C8 C21 H21A 109.6 . . ?
C8 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
O1 C22 C18 109.92(17) . . ?
O1 C22 H22A 109.7 . . ?
O1 C22 H22B 109.7 . . ?
C18 C22 H22A 109.7 . . ?
C18 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
O5 C23 H23A 109.5 . . ?
O5 C23 H23B 109.5 . . ?
O5 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O6 C24 H24A 109.5 . . ?
O6 C24 H24B 109.5 . . ?
O6 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.169
_oxdiff_exptl_absorpt_empirical_full_min 0.646
####################################################################### 
# 
# 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_anti-3a
_database_code_depnum_ccdc_archive 'CCDC 1942739'
loop_
_audit_author_name
_audit_author_address
Fu
;HuaQiao University
China
;
_audit_update_record             
;
2019-11-04 deposited with the CCDC.	2019-12-06 downloaded from the CCDC.
;
_audit_creation_date             2019-11-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C11 H11 N O2)'
_chemical_formula_sum            'C22 H22 N2 O4'
_chemical_formula_weight         378.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.5996(10)
_cell_length_b                   8.1161(5)
_cell_length_c                   16.4481(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.915(7)
_cell_angle_gamma                90
_cell_volume                     1919.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2229
_cell_measurement_temperature    293.1(2)
_cell_measurement_theta_max      25.1780
_cell_measurement_theta_min      3.7760
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.32
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10170
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.332
_diffrn_reflns_theta_min         3.449
_diffrn_ambient_temperature      293.1(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00 -20.00   1.00    7.50    --  -16.12 -57.00 -30.00   31
  2  ω    -84.00  52.00   1.00    7.50    --  -16.12   0.00   0.00  136
  3  ω    -10.00  36.00   1.00    7.50    --   15.49 -77.00 150.00   46
  4  ω     11.00  51.00   1.00    7.50    --  -16.12  57.00-180.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0064892000
_diffrn_orient_matrix_UB_12      0.0143595000
_diffrn_orient_matrix_UB_13      0.0431566000
_diffrn_orient_matrix_UB_21      -0.0413373000
_diffrn_orient_matrix_UB_22      -0.0444118000
_diffrn_orient_matrix_UB_23      0.0022615000
_diffrn_orient_matrix_UB_31      0.0261086000
_diffrn_orient_matrix_UB_32      -0.0738517000
_diffrn_orient_matrix_UB_33      0.0070485000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2192
_reflns_number_total             4506
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4506
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1374
_refine_ls_R_factor_gt           0.0564
_refine_ls_restrained_S_all      0.992
_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)+(0.0508P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1421
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C21B-C20B \\sim C21-C20
 with sigma of 0.01
 C20-C19 \\sim C20B-C19
 with sigma of 0.01
3. Others
 Sof(H19A)=Sof(C20B)=Sof(H20B)=Sof(C21B)=Sof(H21C)=Sof(H21D)=1-FVAR(1)
 Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21A)=Sof(H21B)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C8(H8), C19(H19), C19(H19A)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C22(H22A,H22B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C20(H20), C20B(H20B)
4.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B), C21(H21A,H21B), C21B(H21C,H21D)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.66850(10) 0.55168(18) 0.47977(9) 0.0513(4) Uani 1 1 d . . . . .
O2 O 0.54636(10) 0.40914(19) 0.41461(10) 0.0616(5) Uani 1 1 d . . . . .
N1 N 0.38722(13) 0.5866(3) 0.37267(12) 0.0489(5) Uani 1 1 d . . . . .
H1 H 0.4151(14) 0.500(2) 0.3860(12) 0.041(7) Uiso 1 1 d . . . . .
C1 C 0.44555(15) 0.7219(3) 0.38662(12) 0.0438(5) Uani 1 1 d . . . . .
C2 C 0.54259(14) 0.7028(2) 0.41142(12) 0.0409(5) Uani 1 1 d . . . . .
C3 C 0.59995(16) 0.8422(3) 0.42016(13) 0.0532(6) Uani 1 1 d . . . . .
H3 H 0.663788 0.829128 0.436250 0.064 Uiso 1 1 calc R . . . .
C4 C 0.5641(2) 0.9969(3) 0.40556(15) 0.0670(7) Uani 1 1 d . . . . .
H4 H 0.603118 1.088252 0.409956 0.080 Uiso 1 1 calc R . . . .
C5 C 0.4695(2) 1.0153(3) 0.38428(15) 0.0709(8) Uani 1 1 d . . . . .
H5 H 0.444556 1.120634 0.376244 0.085 Uiso 1 1 calc R . . . .
C6 C 0.41099(18) 0.8820(3) 0.37461(14) 0.0601(7) Uani 1 1 d . . . . .
H6 H 0.347263 0.898490 0.359810 0.072 Uiso 1 1 calc R . . . .
C7 C 0.58342(15) 0.5407(3) 0.43349(13) 0.0436(5) Uani 1 1 d . . . . .
C8 C 0.29270(15) 0.5862(3) 0.38955(14) 0.0543(6) Uani 1 1 d . . . . .
H8 H 0.260993 0.683670 0.363119 0.065 Uiso 1 1 calc R . . . .
C9 C 0.24112(17) 0.4369(4) 0.35219(15) 0.0709(8) Uani 1 1 d . . . . .
H9 H 0.180448 0.425687 0.361681 0.085 Uiso 1 1 calc R . . . .
C10 C 0.2700(2) 0.3225(4) 0.30873(17) 0.0803(8) Uani 1 1 d . . . . .
H10A H 0.330048 0.326597 0.297048 0.096 Uiso 1 1 calc R . . . .
H10B H 0.230806 0.235724 0.288992 0.096 Uiso 1 1 calc R . . . .
C11 C 0.71126(15) 0.4047(3) 0.51876(15) 0.0570(6) Uani 1 1 d . . . . .
H11A H 0.775365 0.397331 0.510578 0.068 Uiso 1 1 calc R . . . .
H11B H 0.678339 0.307763 0.494726 0.068 Uiso 1 1 calc R . . . .
O3 O 0.42931(11) 0.1930(2) -0.11592(9) 0.0654(5) Uani 1 1 d . . . . .
O4 O 0.56726(11) 0.1154(2) -0.04376(9) 0.0598(5) Uani 1 1 d . . . . .
N2 N 0.58969(14) 0.1613(3) 0.12099(13) 0.0612(6) Uani 1 1 d . . . . .
H2 H 0.6087(14) 0.122(3) 0.0820(13) 0.046(7) Uiso 1 1 d . . . . .
C12 C 0.51259(15) 0.2579(3) 0.10342(14) 0.0518(6) Uani 1 1 d . . . . .
C13 C 0.46610(15) 0.2816(3) 0.02151(14) 0.0497(6) Uani 1 1 d . . . . .
C14 C 0.39161(16) 0.3932(3) 0.00579(16) 0.0593(7) Uani 1 1 d . . . . .
H14 H 0.361631 0.409355 -0.048257 0.071 Uiso 1 1 calc R . . . .
C15 C 0.36199(18) 0.4793(3) 0.06859(19) 0.0683(7) Uani 1 1 d . . . . .
H15 H 0.313217 0.554143 0.057219 0.082 Uiso 1 1 calc R . . . .
C16 C 0.4056(2) 0.4528(3) 0.1480(2) 0.0740(8) Uani 1 1 d . . . . .
H16 H 0.385596 0.509947 0.190724 0.089 Uiso 1 1 calc R . . . .
C17 C 0.47835(18) 0.3437(3) 0.16616(16) 0.0664(7) Uani 1 1 d . . . . .
H17 H 0.505385 0.326391 0.220942 0.080 Uiso 1 1 calc R . . . .
C18 C 0.49456(16) 0.1902(3) -0.04714(14) 0.0514(6) Uani 1 1 d . . . . .
C19 C 0.61181(19) 0.0576(4) 0.19410(16) 0.0727(8) Uani 1 1 d D . . . .
H19 H 0.599248 0.120065 0.241957 0.087 Uiso 0.649(10) 1 calc R . P A 1
H19A H 0.591082 0.120772 0.238347 0.087 Uiso 0.351(10) 1 calc R . P A 2
C22 C 0.44643(19) 0.0983(4) -0.18651(15) 0.0745(8) Uani 1 1 d . . . . .
H22A H 0.511828 0.069892 -0.179854 0.089 Uiso 1 1 calc R . . . .
H22B H 0.430574 0.163694 -0.236317 0.089 Uiso 1 1 calc R . . . .
C20 C 0.7164(4) 0.0301(13) 0.2034(5) 0.076(3) Uani 0.649(10) 1 d D . P A 1
H20 H 0.738044 0.003800 0.155013 0.091 Uiso 0.649(10) 1 calc R . P A 1
C21 C 0.7768(4) 0.0379(8) 0.2664(5) 0.114(3) Uani 0.649(10) 1 d D . P A 1
H21A H 0.760094 0.063604 0.316973 0.136 Uiso 0.649(10) 1 calc R . P A 1
H21B H 0.838791 0.017973 0.263053 0.136 Uiso 0.649(10) 1 calc R . P A 1
C20B C 0.7066(6) -0.0071(18) 0.2316(8) 0.081(5) Uani 0.351(10) 1 d D . P A 2
H20B H 0.716599 -0.089509 0.271407 0.097 Uiso 0.351(10) 1 calc R . P A 2
C21B C 0.7691(11) 0.062(2) 0.2033(9) 0.109(5) Uani 0.351(10) 1 d D . P A 2
H21C H 0.754742 0.143943 0.163519 0.131 Uiso 0.351(10) 1 calc R . P A 2
H21D H 0.830801 0.032887 0.221675 0.131 Uiso 0.351(10) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.343(2) . ?
O1 C11 1.444(2) . ?
O2 C7 1.213(2) . ?
N1 H1 0.820(19) . ?
N1 C1 1.384(3) . ?
N1 C8 1.454(3) . ?
C1 C2 1.414(3) . ?
C1 C6 1.396(3) . ?
C2 C3 1.400(3) . ?
C2 C7 1.464(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.366(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.371(3) . ?
C6 H6 0.9300 . ?
C8 H8 0.9800 . ?
C8 C9 1.501(4) . ?
C8 C11 1.521(3) 3_666 ?
C9 H9 0.9300 . ?
C9 C10 1.286(3) . ?
C10 H10A 0.9300 . ?
C10 H10B 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
O3 C18 1.348(3) . ?
O3 C22 1.449(3) . ?
O4 C18 1.216(2) . ?
N2 H2 0.81(2) . ?
N2 C12 1.361(3) . ?
N2 C19 1.458(3) . ?
C12 C13 1.414(3) . ?
C12 C17 1.406(3) . ?
C13 C14 1.405(3) . ?
C13 C18 1.470(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.368(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(3) . ?
C17 H17 0.9300 . ?
C19 H19 0.9800 . ?
C19 H19A 0.9800 . ?
C19 C22 1.517(4) 3_655 ?
C19 C20 1.525(6) . ?
C19 C20B 1.509(8) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C20 H20 0.9300 . ?
C20 C21 1.241(7) . ?
C21 H21A 0.9300 . ?
C21 H21B 0.9300 . ?
C20B H20B 0.9300 . ?
C20B C21B 1.230(9) . ?
C21B H21C 0.9300 . ?
C21B H21D 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C11 118.93(18) . . ?
C1 N1 H1 111.6(14) . . ?
C1 N1 C8 123.2(2) . . ?
C8 N1 H1 113.0(14) . . ?
N1 C1 C2 121.2(2) . . ?
N1 C1 C6 121.2(2) . . ?
C6 C1 C2 117.6(2) . . ?
C1 C2 C7 121.02(19) . . ?
C3 C2 C1 119.5(2) . . ?
C3 C2 C7 119.3(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.9(2) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.6(2) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.0(2) . . ?
C5 C6 H6 119.5 . . ?
O1 C7 C2 112.2(2) . . ?
O2 C7 O1 122.1(2) . . ?
O2 C7 C2 125.6(2) . . ?
N1 C8 H8 107.7 . . ?
N1 C8 C9 110.5(2) . . ?
N1 C8 C11 112.87(18) . 3_666 ?
C9 C8 H8 107.7 . . ?
C9 C8 C11 110.08(19) . 3_666 ?
C11 C8 H8 107.7 3_666 . ?
C8 C9 H9 115.8 . . ?
C10 C9 C8 128.4(2) . . ?
C10 C9 H9 115.8 . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
O1 C11 C8 108.22(17) . 3_666 ?
O1 C11 H11A 110.1 . . ?
O1 C11 H11B 110.1 . . ?
C8 C11 H11A 110.1 3_666 . ?
C8 C11 H11B 110.1 3_666 . ?
H11A C11 H11B 108.4 . . ?
C18 O3 C22 117.99(19) . . ?
C12 N2 H2 116.3(15) . . ?
C12 N2 C19 124.4(2) . . ?
C19 N2 H2 111.8(15) . . ?
N2 C12 C13 121.6(2) . . ?
N2 C12 C17 121.0(2) . . ?
C17 C12 C13 117.3(2) . . ?
C12 C13 C18 120.7(2) . . ?
C14 C13 C12 119.5(2) . . ?
C14 C13 C18 119.8(2) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.5(2) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 120.6 . . ?
C16 C15 C14 118.8(3) . . ?
C16 C15 H15 120.6 . . ?
C15 C16 H16 119.2 . . ?
C15 C16 C17 121.6(3) . . ?
C17 C16 H16 119.2 . . ?
C12 C17 H17 119.4 . . ?
C16 C17 C12 121.2(2) . . ?
C16 C17 H17 119.4 . . ?
O3 C18 C13 112.6(2) . . ?
O4 C18 O3 122.1(2) . . ?
O4 C18 C13 125.2(2) . . ?
N2 C19 H19 108.5 . . ?
N2 C19 H19A 104.9 . . ?
N2 C19 C22 111.9(2) . 3_655 ?
N2 C19 C20 104.1(4) . . ?
N2 C19 C20B 126.5(5) . . ?
C22 C19 H19 108.5 3_655 . ?
C22 C19 H19A 104.9 3_655 . ?
C22 C19 C20 115.1(4) 3_655 . ?
C20 C19 H19 108.5 . . ?
C20B C19 H19A 104.9 . . ?
C20B C19 C22 101.9(6) . 3_655 ?
O3 C22 C19 109.6(2) . 3_655 ?
O3 C22 H22A 109.7 . . ?
O3 C22 H22B 109.7 . . ?
C19 C22 H22A 109.7 3_655 . ?
C19 C22 H22B 109.7 3_655 . ?
H22A C22 H22B 108.2 . . ?
C19 C20 H20 115.4 . . ?
C21 C20 C19 129.2(9) . . ?
C21 C20 H20 115.4 . . ?
C20 C21 H21A 120.0 . . ?
C20 C21 H21B 120.0 . . ?
H21A C21 H21B 120.0 . . ?
C19 C20B H20B 124.0 . . ?
C21B C20B C19 112.0(11) . . ?
C21B C20B H20B 124.0 . . ?
C20B C21B H21C 120.0 . . ?
C20B C21B H21D 120.0 . . ?
H21C C21B H21D 120.0 . . ?

_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 2.216
_oxdiff_exptl_absorpt_empirical_full_min 0.562
