# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_ww
_database_code_depnum_ccdc_archive 'CCDC 2044497'
loop_
_audit_author_name
_audit_author_address
hjw
;Department of Applied Chemistry, Jiang Xi Academic of Sciences
China
;
_audit_update_record             
;
2020-11-16 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;
_audit_creation_date             2020-10-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 N2 O2'
_chemical_formula_sum            'C18 H20 N2 O2'
_chemical_formula_weight         296.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.7762(7)
_cell_length_b                   8.0291(2)
_cell_length_c                   23.0370(8)
_cell_angle_alpha                90
_cell_angle_beta                 112.850(4)
_cell_angle_gamma                90
_cell_volume                     3200.4(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2342
_cell_measurement_temperature    240.00(10)
_cell_measurement_theta_max      72.6230
_cell_measurement_theta_min      4.1480
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.932
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4679
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.571
_diffrn_reflns_theta_max         66.571
_diffrn_reflns_theta_min         4.165
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      240.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6525
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -107.00 -16.00   1.00    2.14    --  -40.20 -38.00 120.00   91
  2  ω    -65.00  24.00   1.00    2.14    --  -40.20  38.00 120.00   89
  3  ω     87.00 171.00   1.00    7.00    --  103.61  30.00 120.00   84
  4  ω     46.00 113.00   1.00    7.00    --  103.61-125.00-150.00   67
  5  ω     29.00 127.00   1.00    7.00    --  103.61 -30.00 -60.00   98
  6  ω     32.00 127.00   1.00    7.00    --  103.61 -77.00-150.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0367524000
_diffrn_orient_matrix_UB_12      -0.0237922000
_diffrn_orient_matrix_UB_13      0.0719127000
_diffrn_orient_matrix_UB_21      0.0811578000
_diffrn_orient_matrix_UB_22      0.0104839000
_diffrn_orient_matrix_UB_23      -0.0017966000
_diffrn_orient_matrix_UB_31      0.0001800000
_diffrn_orient_matrix_UB_32      0.1900091000
_diffrn_orient_matrix_UB_33      0.0090876000
_diffrn_oxdiff_digest_frames     
;
013caf40af379dcc88e4954de8894aace100548ab7e
;
_diffrn_oxdiff_digest_hkl        
;
01430bc1c4721968a2401cb7ffcafcbc0ccc76
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2476
_reflns_number_total             2806
_reflns_odcompleteness_completeness 99.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.00148(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2806
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.041
_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)+(0.0558P)²+1.1136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1067
_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:
 C14(H14), C4(H4), C15(H15), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C12(H12A,H12B), C16(H16A,H16B), C6(H6A,H6B), C13(H13A,H13B),
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
O2 O 0.69861(6) 0.56125(12) 0.39900(5) 0.0444(3) Uani 1 1 d . . . . .
O1 O 0.66634(7) 0.50639(12) 0.29654(5) 0.0477(3) Uani 1 1 d . . . . .
N2 N 0.64026(8) 0.10459(17) 0.26156(6) 0.0494(3) Uani 1 1 d . . . . .
C14 C 0.61040(7) 0.24667(14) 0.39124(6) 0.0302(3) Uani 1 1 d . . . . .
H14 H 0.6256 0.3061 0.4314 0.036 Uiso 1 1 calc R . . . .
C3 C 0.67481(7) 0.27736(14) 0.36513(6) 0.0288(3) Uani 1 1 d . . . . .
C9 C 0.74910(7) 0.04416(16) 0.43501(6) 0.0327(3) Uani 1 1 d . . . . .
C4 C 0.75553(7) 0.21962(15) 0.41281(6) 0.0304(3) Uani 1 1 d . . . . .
H4 H 0.7707 0.2935 0.4495 0.036 Uiso 1 1 calc R . . . .
C10 C 0.68259(8) -0.02427(16) 0.43099(6) 0.0357(3) Uani 1 1 d . . . . .
H10 H 0.6838 -0.1326 0.4456 0.043 Uiso 1 1 calc R . . . .
C18 C 0.65523(8) 0.18428(16) 0.30571(6) 0.0343(3) Uani 1 1 d . . . . .
C2 C 0.68110(8) 0.46564(15) 0.35588(6) 0.0337(3) Uani 1 1 d . . . . .
C11 C 0.60772(7) 0.06116(15) 0.40489(6) 0.0342(3) Uani 1 1 d . . . . .
C15 C 0.53383(8) 0.31680(16) 0.34759(7) 0.0361(3) Uani 1 1 d . . . . .
H15 H 0.5139 0.2686 0.3052 0.043 Uiso 1 1 calc R . . . .
N1 N 0.87383(8) -0.1313(2) 0.48188(8) 0.0627(4) Uani 1 1 d . . . . .
C5 C 0.81657(8) 0.23229(18) 0.38547(7) 0.0386(3) Uani 1 1 d . . . . .
H5 H 0.8079 0.1615 0.3487 0.046 Uiso 1 1 calc R . . . .
C8 C 0.81875(8) -0.05337(18) 0.46102(7) 0.0418(3) Uani 1 1 d . . . . .
C7 C 0.89965(9) 0.2572(2) 0.42803(8) 0.0495(4) Uani 1 1 d . . . . .
H7A H 0.9119 0.2690 0.4728 0.059 Uiso 1 1 calc R . . . .
H7B H 0.9385 0.1997 0.4175 0.059 Uiso 1 1 calc R . . . .
C12 C 0.54677(9) -0.00593(19) 0.42700(8) 0.0480(4) Uani 1 1 d . . . . .
H12A H 0.5621 -0.0935 0.4585 0.058 Uiso 1 1 calc R . . . .
H12B H 0.5094 0.0723 0.4306 0.058 Uiso 1 1 calc R . . . .
C16 C 0.47248(9) 0.36731(19) 0.37073(8) 0.0496(4) Uani 1 1 d . . . . .
H16A H 0.4191 0.3446 0.3437 0.059 Uiso 1 1 calc R . . . .
H16B H 0.4843 0.3575 0.4155 0.059 Uiso 1 1 calc R . . . .
C6 C 0.85613(9) 0.3953(2) 0.38575(8) 0.0524(4) Uani 1 1 d . . . . .
H6A H 0.8686 0.4212 0.3496 0.063 Uiso 1 1 calc R . . . .
H6B H 0.8420 0.4906 0.4049 0.063 Uiso 1 1 calc R . . . .
C13 C 0.54135(9) -0.04838(18) 0.36299(8) 0.0497(4) Uani 1 1 d . . . . .
H13A H 0.5007 0.0041 0.3276 0.060 Uiso 1 1 calc R . . . .
H13B H 0.5534 -0.1618 0.3555 0.060 Uiso 1 1 calc R . . . .
C17 C 0.51410(9) 0.49806(19) 0.34996(8) 0.0502(4) Uani 1 1 d . . . . .
H17A H 0.5512 0.5671 0.3822 0.060 Uiso 1 1 calc R . . . .
H17B H 0.4859 0.5542 0.3103 0.060 Uiso 1 1 calc R . . . .
C1 C 0.67546(15) 0.6825(2) 0.28565(10) 0.0722(6) Uani 1 1 d . . . . .
H1A H 0.6615 0.7013 0.2414 0.108 Uiso 1 1 calc GR . . . .
H1B H 0.7283 0.7147 0.3083 0.108 Uiso 1 1 calc GR . . . .
H1C H 0.6426 0.7474 0.3000 0.108 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.1962(16) . ?
O1 C2 1.3260(16) . ?
O1 C1 1.4574(18) . ?
N2 C18 1.1406(18) . ?
C14 H14 0.9800 . ?
C14 C3 1.5652(16) . ?
C14 C11 1.5272(16) . ?
C14 C15 1.5075(18) . ?
C3 C4 1.5575(17) . ?
C3 C18 1.4754(17) . ?
C3 C2 1.5376(16) . ?
C9 C4 1.5194(17) . ?
C9 C10 1.3342(19) . ?
C9 C8 1.4402(19) . ?
C4 H4 0.9800 . ?
C4 C5 1.5105(17) . ?
C10 H10 0.9300 . ?
C10 C11 1.4669(19) . ?
C11 C12 1.5203(18) . ?
C11 C13 1.5245(19) . ?
C15 H15 0.9800 . ?
C15 C16 1.501(2) . ?
C15 C17 1.5080(19) . ?
N1 C8 1.143(2) . ?
C5 H5 0.9800 . ?
C5 C7 1.499(2) . ?
C5 C6 1.504(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C6 1.492(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.478(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.494(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 115.17(12) . . ?
C3 C14 H14 107.5 . . ?
C11 C14 H14 107.5 . . ?
C11 C14 C3 108.96(10) . . ?
C15 C14 H14 107.5 . . ?
C15 C14 C3 111.35(10) . . ?
C15 C14 C11 113.73(10) . . ?
C4 C3 C14 111.57(10) . . ?
C18 C3 C14 108.99(10) . . ?
C18 C3 C4 109.10(10) . . ?
C18 C3 C2 111.98(10) . . ?
C2 C3 C14 108.69(10) . . ?
C2 C3 C4 106.52(10) . . ?
C10 C9 C4 123.58(12) . . ?
C10 C9 C8 118.64(12) . . ?
C8 C9 C4 117.78(11) . . ?
C3 C4 H4 107.8 . . ?
C9 C4 C3 109.30(10) . . ?
C9 C4 H4 107.8 . . ?
C5 C4 C3 111.96(10) . . ?
C5 C4 C9 112.04(11) . . ?
C5 C4 H4 107.8 . . ?
C9 C10 H10 118.0 . . ?
C9 C10 C11 123.93(12) . . ?
C11 C10 H10 118.0 . . ?
N2 C18 C3 176.29(14) . . ?
O2 C2 O1 125.30(12) . . ?
O2 C2 C3 121.80(12) . . ?
O1 C2 C3 112.90(11) . . ?
C10 C11 C14 115.94(11) . . ?
C10 C11 C12 115.04(11) . . ?
C10 C11 C13 114.04(12) . . ?
C12 C11 C14 120.26(12) . . ?
C12 C11 C13 58.07(10) . . ?
C13 C11 C14 121.09(12) . . ?
C14 C15 H15 114.4 . . ?
C14 C15 C17 121.36(12) . . ?
C16 C15 C14 121.93(12) . . ?
C16 C15 H15 114.4 . . ?
C16 C15 C17 59.54(10) . . ?
C17 C15 H15 114.4 . . ?
C4 C5 H5 115.1 . . ?
C7 C5 C4 120.11(12) . . ?
C7 C5 H5 115.1 . . ?
C7 C5 C6 59.61(10) . . ?
C6 C5 C4 120.69(12) . . ?
C6 C5 H5 115.1 . . ?
N1 C8 C9 179.57(17) . . ?
C5 C7 H7A 117.7 . . ?
C5 C7 H7B 117.7 . . ?
H7A C7 H7B 114.9 . . ?
C6 C7 C5 60.36(10) . . ?
C6 C7 H7A 117.7 . . ?
C6 C7 H7B 117.7 . . ?
C11 C12 H12A 117.7 . . ?
C11 C12 H12B 117.7 . . ?
H12A C12 H12B 114.8 . . ?
C13 C12 C11 61.11(10) . . ?
C13 C12 H12A 117.7 . . ?
C13 C12 H12B 117.7 . . ?
C15 C16 H16A 117.7 . . ?
C15 C16 H16B 117.7 . . ?
H16A C16 H16B 114.8 . . ?
C17 C16 C15 60.47(10) . . ?
C17 C16 H16A 117.7 . . ?
C17 C16 H16B 117.7 . . ?
C5 C6 H6A 117.8 . . ?
C5 C6 H6B 117.8 . . ?
C7 C6 C5 60.03(10) . . ?
C7 C6 H6A 117.8 . . ?
C7 C6 H6B 117.8 . . ?
H6A C6 H6B 114.9 . . ?
C11 C13 H13A 117.7 . . ?
C11 C13 H13B 117.7 . . ?
C12 C13 C11 60.82(9) . . ?
C12 C13 H13A 117.7 . . ?
C12 C13 H13B 117.7 . . ?
H13A C13 H13B 114.8 . . ?
C15 C17 H17A 117.8 . . ?
C15 C17 H17B 117.8 . . ?
C16 C17 C15 59.98(10) . . ?
C16 C17 H17A 117.8 . . ?
C16 C17 H17B 117.8 . . ?
H17A C17 H17B 114.9 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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 1.354
_oxdiff_exptl_absorpt_empirical_full_min 0.483
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2092194'
loop_
_audit_author_name
_audit_author_address
hjw
;Department of Applied Chemistry, Jiang Xi Academic of Sciences
China
;
_audit_update_record             
;
2021-06-25 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;
_audit_creation_date             2021-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 Cl2 N2 O3'
_chemical_formula_sum            'C16 H14 Cl2 N2 O3'
_chemical_formula_weight         353.19
_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'
Cl Cl 0.1484 0.1585 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   33.761(16)
_cell_length_b                   6.7432(19)
_cell_length_c                   14.595(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.90(3)
_cell_angle_gamma                90
_cell_volume                     3251(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7665
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.944
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5900
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1033 before and 0.0696 after correction.
The Ratio of minimum to maximum transmission is 0.7913.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18429
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.008
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_min         2.069
_diffrn_ambient_temperature      250.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3245
_reflns_number_total             3832
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3832
_refine_ls_number_restraints     149
_refine_ls_R_factor_all          0.1233
_refine_ls_R_factor_gt           0.1106
_refine_ls_restrained_S_all      1.075
_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)+(0.0020P)²+20.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2234
_refine_ls_wR_factor_ref         0.2298
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.586(2)
 0.414(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C14A-O2A
 1.3 with sigma of 0.02
 C14A-C13
 1.45 with sigma of 0.02
 C13-C14
 1.5 with sigma of 0.02
 C14-O3
 1.28 with sigma of 0.02
 C14-O2
 1.3 with sigma of 0.02
 C14A-O3A
 1.3 with sigma of 0.02
 O2A-C15A
 1.55 with sigma of 0.02
 C15-O2
 1.5 with sigma of 0.02
 C15A-O2A
 1.43 with sigma of 0.02
 C15A-C16A
 1.5 with sigma of 0.02
 C15-C16
 1.5 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
O3A \\sim C14A \\sim C14 \\sim O3 \\sim O2A \\sim O2 \\sim C15A \\sim C15:
within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(O3) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(O3A) \\sim Ueq, Uanis(C14)
\\sim Ueq, Uanis(C14A) \\sim Ueq, Uanis(O2A) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C12) \\sim Ueq, Uanis(C12A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C12) = Uanis(C12A)
5. Others
 Sof(H11C)=Sof(H11D)=Sof(C12A)=Sof(H12C)=Sof(H12D)=1-FVAR(1)
 Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=FVAR(1)
 Fixed Sof: O3(0.5) O2(0.5) O3A(0.5) C14(0.5) C14A(0.5) O2A(0.5) C15(0.5)
 H15A(0.5) H15B(0.5) C15A(0.5) H15C(0.5) H15D(0.5) Cl2(0.5) Cl2A(0.5) C16A(0.5)
 H16A(0.5) H16B(0.5) H16C(0.5) C16(0.5) H16D(0.5) H16E(0.5) H16F(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C11(H11C,H11D), C12(H12A,H12B), C12A(H12C,H12D), C15(H15A,
 H15B), C15A(H15C,H15D)
6.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C1(H1), C10(H10), C2(H2)
6.c Idealised Me refined as rotating group:
 C16A(H16A,H16B,H16C), C16(H16D,H16E,H16F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.17058(5) 0.0672(3) 0.68228(12) 0.0785(5) Uani 1 1 d . . . . .
C4 C 0.25225(16) 0.0776(7) 0.7309(4) 0.0594(14) Uani 1 1 d . . . . .
H4 H 0.2523 0.0923 0.6669 0.071 Uiso 1 1 calc R . . . .
O1 O 0.18012(10) -0.2959(4) 0.9010(3) 0.0644(10) Uani 1 1 d . . . . .
N1 N 0.17773(11) 0.0419(5) 0.8870(3) 0.0441(9) Uani 1 1 d . . . . .
C6 C 0.21573(14) 0.0461(6) 0.8534(4) 0.0453(12) Uani 1 1 d . . . . .
C3 C 0.28780(15) 0.0683(7) 0.7976(4) 0.0611(15) Uani 1 1 d . . . . .
H3 H 0.3126 0.0787 0.7782 0.073 Uiso 1 1 calc R . . . .
C5 C 0.21560(14) 0.0639(6) 0.7637(4) 0.0470(12) Uani 1 1 d . . . . .
N2 N 0.12320(12) 0.2366(6) 0.9145(4) 0.0671(13) Uani 1 1 d . . . . .
C8 C 0.12412(13) -0.1193(7) 0.9369(4) 0.0483(12) Uani 1 1 d . . . . .
C7 C 0.16212(13) -0.1448(6) 0.9087(4) 0.0482(12) Uani 1 1 d . . . . .
C1 C 0.25178(15) 0.0325(7) 0.9205(5) 0.0623(16) Uani 1 1 d . . . . .
H1 H 0.2519 0.0157 0.9844 0.075 Uiso 1 1 calc R . . . .
C9 C 0.10735(14) 0.0608(7) 0.9382(4) 0.0544(13) Uani 1 1 d . . . . .
C10 C 0.15777(15) 0.2167(7) 0.8914(5) 0.0677(17) Uani 1 1 d . . . . .
H10 H 0.1704 0.3329 0.8762 0.081 Uiso 1 1 calc R . . . .
C2 C 0.28809(16) 0.0453(8) 0.8869(5) 0.0640(16) Uani 1 1 d . . . . .
H2 H 0.3130 0.0373 0.9296 0.077 Uiso 1 1 calc R . . . .
C11 C 0.09828(15) -0.2802(8) 0.9649(4) 0.0682(16) Uani 1 1 d . . . . .
H11A H 0.1142 -0.3677 1.0123 0.082 Uiso 0.567(11) 1 calc R . P A 1
H11B H 0.0853 -0.3596 0.9108 0.082 Uiso 0.567(11) 1 calc R . P A 1
H11C H 0.1086 -0.3224 1.0297 0.082 Uiso 0.433(11) 1 calc R . P A 2
H11D H 0.0968 -0.3955 0.9235 0.082 Uiso 0.433(11) 1 calc R . P A 2
C13 C 0.06636(16) 0.0466(9) 0.9645(5) 0.0728(18) Uani 1 1 d D . . . .
C12 C 0.0662(3) -0.1598(16) 1.0061(8) 0.064(2) Uani 0.567(11) 1 d . U P A 1
H12A H 0.0394 -0.2204 0.9880 0.076 Uiso 0.567(11) 1 calc R . P A 1
H12B H 0.0738 -0.1546 1.0746 0.076 Uiso 0.567(11) 1 calc R . P A 1
O3 O 0.0326(3) 0.3466(15) 0.9984(9) 0.116(4) Uani 0.5 1 d D U P A 1
O2 O 0.0843(3) 0.2287(17) 1.0990(7) 0.109(3) Uani 0.5 1 d D U P A 1
O3A O 0.0779(5) 0.011(2) 1.1379(10) 0.158(6) Uani 0.5 1 d D U P A 2
C14 C 0.0569(4) 0.2140(18) 1.0226(9) 0.085(4) Uani 0.5 1 d D U P A 1
C14A C 0.0712(4) 0.1079(18) 1.0655(8) 0.082(4) Uani 0.5 1 d D U P A 2
O2A O 0.0601(4) 0.2788(19) 1.0840(8) 0.154(5) Uani 0.5 1 d D U P A 2
C12A C 0.0577(4) -0.180(2) 0.9543(11) 0.064(2) Uani 0.433(11) 1 d . U P A 2
H12C H 0.0436 -0.2255 1.0028 0.076 Uiso 0.433(11) 1 calc R . P A 2
H12D H 0.0407 -0.2093 0.8928 0.076 Uiso 0.433(11) 1 calc R . P A 2
C15 C 0.0831(5) 0.364(3) 1.1805(11) 0.137(7) Uani 0.5 1 d D U P A 1
H15A H 0.1001 0.2987 1.2346 0.164 Uiso 0.5 1 calc R . P A 1
H15B H 0.0980 0.4827 1.1687 0.164 Uiso 0.5 1 calc R . P A 1
C15A C 0.0530(5) 0.330(3) 1.1796(9) 0.159(8) Uani 0.5 1 d D U P A 2
H15C H 0.0279 0.4046 1.1773 0.190 Uiso 0.5 1 calc R . P A 2
H15D H 0.0538 0.2137 1.2202 0.190 Uiso 0.5 1 calc R . P A 2
Cl2 Cl 0.02859(11) 0.0725(7) 0.8502(4) 0.1078(15) Uani 0.5 1 d . . P A 1
Cl2A Cl 0.02981(9) 0.1770(8) 0.8976(3) 0.1058(14) Uani 0.5 1 d . . P A 2
C16A C 0.0895(6) 0.455(3) 1.2052(15) 0.176(8) Uani 0.5 1 d D . P A 2
H16A H 0.0938 0.5261 1.1504 0.263 Uiso 0.5 1 calc GR . P A 2
H16B H 0.1128 0.3716 1.2290 0.263 Uiso 0.5 1 calc GR . P A 2
H16C H 0.0859 0.5489 1.2531 0.263 Uiso 0.5 1 calc GR . P A 2
C16 C 0.0475(6) 0.441(4) 1.2158(19) 0.214(13) Uani 0.5 1 d D . P A 1
H16D H 0.0275 0.4918 1.1637 0.321 Uiso 0.5 1 calc GR . P A 1
H16E H 0.0563 0.5465 1.2605 0.321 Uiso 0.5 1 calc GR . P A 1
H16F H 0.0358 0.3344 1.2460 0.321 Uiso 0.5 1 calc GR . P A 1


_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
Cl1 C5 1.726(5) . ?
C4 C3 1.382(7) . ?
C4 C5 1.419(7) . ?
O1 C7 1.204(5) . ?
N1 C6 1.465(6) . ?
N1 C7 1.425(6) . ?
N1 C10 1.366(6) . ?
C6 C5 1.313(7) . ?
C6 C1 1.398(7) . ?
C3 C2 1.311(8) . ?
N2 C9 1.374(6) . ?
N2 C10 1.287(7) . ?
C8 C7 1.436(6) . ?
C8 C9 1.342(7) . ?
C8 C11 1.502(7) . ?
C1 C2 1.414(8) . ?
C9 C13 1.513(7) . ?
C11 C12 1.568(11) . ?
C11 C12A 1.508(13) . ?
C13 C12 1.519(12) . ?
C13 C14 1.485(12) . ?
C13 C14A 1.507(12) . ?
C13 C12A 1.556(15) . ?
C13 Cl2 1.887(8) . ?
C13 Cl2A 1.659(7) . ?
O3 C14 1.215(13) . ?
O2 C14 1.299(13) . ?
O2 C15 1.507(15) . ?
O3A C14A 1.224(15) . ?
C14A O2A 1.258(14) . ?
O2A C15A 1.504(13) . ?
C15 C16 1.493(18) . ?
C15A C16A 1.475(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C4 C5 116.8(5) . . ?
C7 N1 C6 118.8(4) . . ?
C10 N1 C6 118.3(4) . . ?
C10 N1 C7 122.9(4) . . ?
C5 C6 N1 120.8(4) . . ?
C5 C6 C1 121.8(5) . . ?
C1 C6 N1 117.4(5) . . ?
C2 C3 C4 122.2(5) . . ?
C4 C5 Cl1 118.2(4) . . ?
C6 C5 Cl1 120.6(4) . . ?
C6 C5 C4 121.2(5) . . ?
C10 N2 C9 113.4(4) . . ?
C7 C8 C11 126.5(4) . . ?
C9 C8 C7 121.1(4) . . ?
C9 C8 C11 112.3(4) . . ?
O1 C7 N1 120.6(4) . . ?
O1 C7 C8 128.8(4) . . ?
N1 C7 C8 110.6(4) . . ?
C6 C1 C2 116.4(6) . . ?
N2 C9 C13 122.8(4) . . ?
C8 C9 N2 126.1(5) . . ?
C8 C9 C13 110.9(5) . . ?
N2 C10 N1 125.8(5) . . ?
C3 C2 C1 121.5(6) . . ?
C8 C11 C12 102.4(5) . . ?
C8 C11 C12A 102.4(6) . . ?
C9 C13 C12 103.7(5) . . ?
C9 C13 C12A 101.7(6) . . ?
C9 C13 Cl2 104.8(5) . . ?
C9 C13 Cl2A 115.2(5) . . ?
C12 C13 Cl2 112.4(5) . . ?
C14 C13 C9 114.4(7) . . ?
C14 C13 C12 116.7(8) . . ?
C14 C13 Cl2 104.4(6) . . ?
C14A C13 C9 108.2(7) . . ?
C14A C13 C12A 110.0(9) . . ?
C14A C13 Cl2A 110.3(6) . . ?
C12A C13 Cl2A 111.2(6) . . ?
C13 C12 C11 105.3(7) . . ?
C14 O2 C15 126.4(11) . . ?
O3 C14 C13 127.3(11) . . ?
O3 C14 O2 120.8(12) . . ?
O2 C14 C13 110.4(9) . . ?
O3A C14A C13 131.4(12) . . ?
O3A C14A O2A 108.4(13) . . ?
O2A C14A C13 118.9(10) . . ?
C14A O2A C15A 121.4(14) . . ?
C11 C12A C13 106.3(8) . . ?
C16 C15 O2 129.6(15) . . ?
C16A C15A O2A 94.7(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.586(2)
2 0.414(2)

####################################################################### 
# 
# 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_WW
_database_code_depnum_ccdc_archive 'CCDC 2044495'
loop_
_audit_author_name
_audit_author_address
hjw
;Department of Applied Chemistry, Jiang Xi Academic of Sciences
China
;
_audit_update_record             
;
2020-11-16 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 N2 O6'
_chemical_formula_weight         338.35

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

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                   12.2878(18)
_cell_length_b                   7.4046(10)
_cell_length_c                   19.762(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.091(2)
_cell_angle_gamma                90
_cell_volume                     1758.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2624
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      23.94

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10224
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.175
_diffrn_reflns_theta_max         27.549
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3996
_reflns_number_gt                2351
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1300P)²+0.8944P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3996
_refine_ls_number_parameters     221
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0778
_refine_ls_wR_factor_ref         0.2531
_refine_ls_wR_factor_gt          0.2173
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.180
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.03559(19) 0.3630(4) 0.69354(14) 0.0658(7) Uani 1 1 d . . . . .
O2 O 0.48463(18) 0.2053(3) 0.57376(12) 0.0549(6) Uani 1 1 d . . . . .
O3 O 0.66231(18) 0.5675(3) 0.65034(10) 0.0465(6) Uani 1 1 d . . . . .
H3 H 0.643381 0.652367 0.623849 0.070 Uiso 1 1 calc R U . . .
O4 O 0.8822(2) -0.0213(4) 0.69301(15) 0.0687(7) Uani 1 1 d . . . . .
O5 O 0.9026(3) -0.0311(5) 0.58375(18) 0.1128(13) Uani 1 1 d . U . . .
N1 N 0.4662(2) 0.4285(3) 0.64900(13) 0.0431(6) Uani 1 1 d . . . . .
H1 H 0.502213 0.516494 0.671781 0.052 Uiso 1 1 calc R U . . .
N2 N 0.7231(2) 0.2344(4) 0.71902(14) 0.0521(7) Uani 1 1 d . . . . .
H2A H 0.765507 0.152845 0.741687 0.062 Uiso 1 1 calc R U . . .
H2B H 0.681848 0.299438 0.739584 0.062 Uiso 1 1 calc R U . . .
C1 C 0.0050(3) 0.4505(7) 0.7504(3) 0.0851(14) Uani 1 1 d . . . . .
H1A H -0.071622 0.425168 0.750371 0.128 Uiso 1 1 calc R U . . .
H1B H 0.050938 0.407279 0.792702 0.128 Uiso 1 1 calc R U . . .
H1C H 0.014976 0.578479 0.746787 0.128 Uiso 1 1 calc R U . . .
C2 C 0.1431(2) 0.3837(4) 0.68495(17) 0.0483(8) Uani 1 1 d . . . . .
C3 C 0.2223(3) 0.4864(5) 0.72725(19) 0.0547(9) Uani 1 1 d . . . . .
H3A H 0.204806 0.549504 0.764256 0.066 Uiso 1 1 calc R U . . .
C4 C 0.3286(3) 0.4950(4) 0.71413(18) 0.0515(8) Uani 1 1 d . . . . .
H4 H 0.382497 0.563441 0.743161 0.062 Uiso 1 1 calc R U . . .
C5 C 0.3565(2) 0.4051(4) 0.65933(15) 0.0406(7) Uani 1 1 d . . . . .
C6 C 0.2756(3) 0.3022(4) 0.61636(17) 0.0495(8) Uani 1 1 d . . . . .
H6 H 0.292616 0.240695 0.578884 0.059 Uiso 1 1 calc R U . . .
C7 C 0.1703(3) 0.2919(5) 0.62960(18) 0.0532(8) Uani 1 1 d . . . . .
H7 H 0.116511 0.222345 0.601013 0.064 Uiso 1 1 calc R U . . .
C8 C 0.5224(2) 0.3368(4) 0.60985(14) 0.0373(6) Uani 1 1 d . . . . .
C9 C 0.6423(2) 0.4020(4) 0.61298(15) 0.0403(7) Uani 1 1 d . . . . .
C10 C 0.7212(2) 0.2603(4) 0.65176(15) 0.0407(7) Uani 1 1 d . . . . .
C11 C 0.7775(3) 0.1762(5) 0.60977(18) 0.0521(8) Uani 1 1 d . . . . .
C12 C 0.7465(4) 0.2452(6) 0.5366(2) 0.0755(12) Uani 1 1 d . . . . .
H12A H 0.706843 0.153713 0.505913 0.091 Uiso 1 1 calc R U . . .
H12B H 0.812193 0.281128 0.520011 0.091 Uiso 1 1 calc R U . . .
C13 C 0.6717(3) 0.4077(5) 0.54113(17) 0.0529(8) Uani 1 1 d . . . . .
H13A H 0.604702 0.401178 0.505158 0.064 Uiso 1 1 calc R U . . .
H13B H 0.710426 0.519005 0.535391 0.064 Uiso 1 1 calc R U . . .
C14 C 0.8567(3) 0.0352(5) 0.6337(2) 0.0655(10) Uani 1 1 d . . . . .
C15 C 0.9896(6) -0.1703(10) 0.6049(4) 0.144(2) Uani 1 1 d D U . . .
H15A H 1.062842 -0.117502 0.608385 0.173 Uiso 1 1 calc R U . . .
H15B H 0.985097 -0.219851 0.649631 0.173 Uiso 1 1 calc R U . . .
C16 C 0.9739(10) -0.2918(14) 0.5600(5) 0.226(5) Uani 1 1 d D U . . .
H16A H 1.029379 -0.383990 0.572514 0.340 Uiso 1 1 calc R U . . .
H16B H 0.901343 -0.343382 0.557066 0.340 Uiso 1 1 calc R U . . .
H16C H 0.978774 -0.241446 0.515987 0.340 Uiso 1 1 calc R U . . .
O6 O 0.5706(4) -0.1619(4) 0.56978(15) 0.1040(13) Uani 1 1 d G U . . .
H6A H 0.550076 -0.054424 0.575618 0.156 Uiso 1 1 d G U . . .
H6B H 0.566747 -0.170420 0.526465 0.156 Uiso 1 1 d G U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.375(4) . ?
O1 C1 1.415(5) . ?
O2 C8 1.238(3) . ?
O3 C9 1.425(3) . ?
O3 H3 0.8200 . ?
O4 C14 1.221(4) . ?
O5 C14 1.330(5) . ?
O5 C15 1.481(7) . ?
N1 C8 1.327(4) . ?
N1 C5 1.416(4) . ?
N1 H1 0.8600 . ?
N2 C10 1.338(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.373(5) . ?
C2 C7 1.387(5) . ?
C3 C4 1.386(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(4) . ?
C6 C7 1.374(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.539(4) . ?
C9 C10 1.523(4) . ?
C9 C13 1.538(4) . ?
C10 C11 1.340(4) . ?
C11 C14 1.438(5) . ?
C11 C12 1.505(5) . ?
C12 C13 1.528(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 C16 1.250(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O6 H6A 0.8501 . ?
O6 H6B 0.8498 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 118.0(3) . . ?
C9 O3 H3 109.5 . . ?
C14 O5 C15 116.2(4) . . ?
C8 N1 C5 130.5(2) . . ?
C8 N1 H1 114.8 . . ?
C5 N1 H1 114.8 . . ?
C10 N2 H2A 120.0 . . ?
C10 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 O1 124.3(3) . . ?
C3 C2 C7 119.6(3) . . ?
O1 C2 C7 116.1(3) . . ?
C2 C3 C4 119.2(3) . . ?
C2 C3 H3A 120.4 . . ?
C4 C3 H3A 120.4 . . ?
C5 C4 C3 121.7(3) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 118.8(3) . . ?
C4 C5 N1 117.1(3) . . ?
C6 C5 N1 124.0(3) . . ?
C7 C6 C5 119.7(3) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C2 121.0(3) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
O2 C8 N1 124.1(3) . . ?
O2 C8 C9 120.7(2) . . ?
N1 C8 C9 115.3(2) . . ?
O3 C9 C10 108.0(2) . . ?
O3 C9 C13 114.0(2) . . ?
C10 C9 C13 103.6(2) . . ?
O3 C9 C8 110.5(2) . . ?
C10 C9 C8 107.9(2) . . ?
C13 C9 C8 112.3(2) . . ?
N2 C10 C11 130.2(3) . . ?
N2 C10 C9 118.4(3) . . ?
C11 C10 C9 111.5(3) . . ?
C10 C11 C14 122.3(3) . . ?
C10 C11 C12 112.2(3) . . ?
C14 C11 C12 125.5(3) . . ?
C11 C12 C13 104.2(3) . . ?
C11 C12 H12A 110.9 . . ?
C13 C12 H12A 110.9 . . ?
C11 C12 H12B 110.9 . . ?
C13 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
C12 C13 C9 107.0(3) . . ?
C12 C13 H13A 110.3 . . ?
C9 C13 H13A 110.3 . . ?
C12 C13 H13B 110.3 . . ?
C9 C13 H13B 110.3 . . ?
H13A C13 H13B 108.6 . . ?
O4 C14 O5 121.5(3) . . ?
O4 C14 C11 125.8(3) . . ?
O5 C14 C11 112.7(4) . . ?
C16 C15 O5 107.8(7) . . ?
C16 C15 H15A 110.1 . . ?
O5 C15 H15A 110.1 . . ?
C16 C15 H15B 110.1 . . ?
O5 C15 H15B 110.1 . . ?
H15A C15 H15B 108.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
H6A O6 H6B 104.5 . . ?

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
C1 O1 C2 C3 -1.2(5) . . . . ?
C1 O1 C2 C7 178.4(3) . . . . ?
O1 C2 C3 C4 179.0(3) . . . . ?
C7 C2 C3 C4 -0.6(5) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C3 C4 C5 N1 177.6(3) . . . . ?
C8 N1 C5 C4 166.2(3) . . . . ?
C8 N1 C5 C6 -16.0(5) . . . . ?
C4 C5 C6 C7 -0.3(5) . . . . ?
N1 C5 C6 C7 -178.1(3) . . . . ?
C5 C6 C7 C2 0.5(5) . . . . ?
C3 C2 C7 C6 0.0(5) . . . . ?
O1 C2 C7 C6 -179.7(3) . . . . ?
C5 N1 C8 O2 -0.5(5) . . . . ?
C5 N1 C8 C9 -179.1(3) . . . . ?
O2 C8 C9 O3 172.6(2) . . . . ?
N1 C8 C9 O3 -8.7(3) . . . . ?
O2 C8 C9 C10 -69.5(3) . . . . ?
N1 C8 C9 C10 109.2(3) . . . . ?
O2 C8 C9 C13 44.0(4) . . . . ?
N1 C8 C9 C13 -137.2(3) . . . . ?
O3 C9 C10 N2 53.0(3) . . . . ?
C13 C9 C10 N2 174.2(3) . . . . ?
C8 C9 C10 N2 -66.5(3) . . . . ?
O3 C9 C10 C11 -128.5(3) . . . . ?
C13 C9 C10 C11 -7.3(4) . . . . ?
C8 C9 C10 C11 111.9(3) . . . . ?
N2 C10 C11 C14 -1.2(6) . . . . ?
C9 C10 C11 C14 -179.4(3) . . . . ?
N2 C10 C11 C12 178.0(3) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C11 C12 C13 7.7(5) . . . . ?
C14 C11 C12 C13 -173.1(4) . . . . ?
C11 C12 C13 C9 -11.9(4) . . . . ?
O3 C9 C13 C12 128.8(3) . . . . ?
C10 C9 C13 C12 11.7(4) . . . . ?
C8 C9 C13 C12 -104.5(3) . . . . ?
C15 O5 C14 O4 -2.8(7) . . . . ?
C15 O5 C14 C11 176.8(5) . . . . ?
C10 C11 C14 O4 -0.9(6) . . . . ?
C12 C11 C14 O4 180.0(4) . . . . ?
C10 C11 C14 O5 179.5(4) . . . . ?
C12 C11 C14 O5 0.4(6) . . . . ?
C14 O5 C15 C16 137.6(9) . . . . ?

_refine_diff_density_max         0.887
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.059

