# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_200708_s2_lgg_zif1
_database_code_depnum_ccdc_archive 'CCDC 2015560'
loop_
_audit_author_name
_audit_author_address
Luo
;Southwest Jiaotong University
China
;
_audit_update_record             
;
2020-07-10 deposited with the CCDC.	2021-09-29 downloaded from the CCDC.
;
_audit_creation_date             2020-07-10
_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         'C25 H25 N3 O4'
_chemical_formula_sum            'C25 H25 N3 O4'
_chemical_formula_weight         431.48
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   11.3360(4)
_cell_length_b                   11.9463(3)
_cell_length_c                   16.0968(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2179.89(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2098
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3930
_cell_measurement_theta_min      3.5360
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6852
_diffrn_reflns_point_group_measured_fraction_full 0.913
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         3.052
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -82.00    3.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -38.0000 -150.0000 85

#__ type_ start__ end____ width___ exp.time_
  2 omega  -19.00    8.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -99.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -21.00   17.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773    0.0000   30.0000 38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0474002000
_diffrn_orient_matrix_UB_12      -0.0057745000
_diffrn_orient_matrix_UB_13      0.0283319000
_diffrn_orient_matrix_UB_21      0.0407003000
_diffrn_orient_matrix_UB_22      -0.0052912000
_diffrn_orient_matrix_UB_23      0.0332562000
_diffrn_orient_matrix_UB_31      -0.0011669000
_diffrn_orient_matrix_UB_32      0.0589149000
_diffrn_orient_matrix_UB_33      0.0058618000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.584
_reflns_Friedel_fraction_full    0.800
_reflns_Friedel_fraction_max     0.764
_reflns_number_gt                2910
_reflns_number_total             3988
_reflns_odcompleteness_completeness 99.65
_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, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 876 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         3988
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0567
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0612P)²+0.4900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1399
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C18-C19
 1.55 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B), C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C21(H21), C22(H22), C23(H23), C24(H24),
 C25(H25)
3.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.8159(4) 0.7817(3) 0.4156(3) 0.0985(15) Uani 1 1 d . . . . .
O2 O 0.6984(3) 0.8003(2) 0.5256(2) 0.0663(10) Uani 1 1 d . . . . .
O3 O 0.8825(3) 0.6410(3) 0.5916(2) 0.0765(11) Uani 1 1 d . . . . .
O4 O 0.7521(3) 0.5031(2) 0.60450(17) 0.0516(7) Uani 1 1 d . . . . .
N1 N 0.5457(3) 0.6606(3) 0.4189(2) 0.0464(9) Uani 1 1 d . . . . .
H1 H 0.507(4) 0.721(3) 0.435(3) 0.060(13) Uiso 1 1 d . . . . .
N2 N 0.8039(3) 0.5541(2) 0.4208(2) 0.0442(8) Uani 1 1 d . . . . .
N3 N 0.6761(3) 0.2988(2) 0.4806(2) 0.0483(9) Uani 1 1 d . . . . .
C1 C 0.5703(3) 0.4692(3) 0.4638(3) 0.0397(9) Uani 1 1 d . . . . .
C2 C 0.5033(3) 0.4795(3) 0.3826(3) 0.0409(9) Uani 1 1 d . . . . .
C3 C 0.4574(4) 0.3974(4) 0.3326(3) 0.0529(11) Uani 1 1 d . . . . .
H3 H 0.4692 0.3223 0.3453 0.063 Uiso 1 1 calc R . . . .
C4 C 0.3931(4) 0.4278(4) 0.2627(3) 0.0639(13) Uani 1 1 d . . . . .
H4 H 0.3618 0.3729 0.2282 0.077 Uiso 1 1 calc R . . . .
C5 C 0.3755(4) 0.5399(4) 0.2441(3) 0.0603(13) Uani 1 1 d . . . . .
H5 H 0.3316 0.5596 0.1976 0.072 Uiso 1 1 calc R . . . .
C6 C 0.4229(4) 0.6232(4) 0.2944(3) 0.0537(11) Uani 1 1 d . . . . .
H6 H 0.4113 0.6984 0.2821 0.064 Uiso 1 1 calc R . . . .
C7 C 0.4880(3) 0.5912(3) 0.3635(3) 0.0413(9) Uani 1 1 d . . . . .
C8 C 0.6015(3) 0.5942(3) 0.4848(2) 0.0381(9) Uani 1 1 d . . . . .
H8 H 0.5683 0.6147 0.5389 0.046 Uiso 1 1 calc R . . . .
C9 C 0.7370(3) 0.6161(3) 0.4842(3) 0.0412(9) Uani 1 1 d . . . . .
C10 C 0.7800(3) 0.4513(3) 0.4077(2) 0.0381(9) Uani 1 1 d . . . . .
C11 C 0.6797(3) 0.3981(3) 0.4518(2) 0.0380(9) Uani 1 1 d . . . . .
C12 C 0.5621(4) 0.2843(3) 0.5239(3) 0.0537(11) Uani 1 1 d . . . . .
H12A H 0.5745 0.2522 0.5785 0.064 Uiso 1 1 calc R . . . .
H12B H 0.5110 0.2349 0.4924 0.064 Uiso 1 1 calc R . . . .
C13 C 0.5066(4) 0.4008(3) 0.5313(3) 0.0482(10) Uani 1 1 d . . . . .
H13A H 0.5202 0.4324 0.5860 0.058 Uiso 1 1 calc R . . . .
H13B H 0.4224 0.3980 0.5209 0.058 Uiso 1 1 calc R . . . .
C14 C 0.7981(4) 0.5906(3) 0.5672(3) 0.0458(10) Uani 1 1 d . . . . .
C15 C 0.8139(5) 0.4637(4) 0.6786(3) 0.0644(13) Uani 1 1 d . . . . .
H15A H 0.8105 0.5201 0.7219 0.077 Uiso 1 1 calc R . . . .
H15B H 0.8961 0.4492 0.6658 0.077 Uiso 1 1 calc R . . . .
C16 C 0.7560(6) 0.3598(4) 0.7071(3) 0.0783(16) Uani 1 1 d . . . . .
H16A H 0.7885 0.3378 0.7597 0.117 Uiso 1 1 calc GR . . . .
H16B H 0.7690 0.3015 0.6671 0.117 Uiso 1 1 calc GR . . . .
H16C H 0.6728 0.3727 0.7130 0.117 Uiso 1 1 calc GR . . . .
C17 C 0.7578(4) 0.7415(3) 0.4686(3) 0.0540(12) Uani 1 1 d . . . . .
C18 C 0.7149(5) 0.9216(4) 0.5274(5) 0.102(2) Uani 1 1 d D . . . .
H18A H 0.7241 0.9456 0.5846 0.122 Uiso 1 1 calc R . . . .
H18B H 0.7869 0.9402 0.4979 0.122 Uiso 1 1 calc R . . . .
C19 C 0.6288(9) 0.9749(6) 0.4945(8) 0.210(6) Uani 1 1 d D . . . .
H19A H 0.5847 0.9253 0.4593 0.315 Uiso 1 1 calc GR . . . .
H19B H 0.6587 1.0360 0.4621 0.315 Uiso 1 1 calc GR . . . .
H19C H 0.5783 1.0033 0.5375 0.315 Uiso 1 1 calc GR . . . .
C20 C 0.8501(3) 0.3885(3) 0.3454(3) 0.0422(9) Uani 1 1 d . . . . .
C21 C 0.9495(4) 0.4387(4) 0.3098(3) 0.0622(13) Uani 1 1 d . . . . .
H21 H 0.9725 0.5097 0.3269 0.075 Uiso 1 1 calc R . . . .
C22 C 1.0137(5) 0.3838(4) 0.2496(3) 0.0674(13) Uani 1 1 d . . . . .
H22 H 1.0807 0.4172 0.2273 0.081 Uiso 1 1 calc R . . . .
C23 C 0.9790(4) 0.2797(4) 0.2223(3) 0.0653(14) Uani 1 1 d . . . . .
H23 H 1.0207 0.2436 0.1804 0.078 Uiso 1 1 calc R . . . .
C24 C 0.8825(5) 0.2297(5) 0.2576(4) 0.0743(15) Uani 1 1 d . . . . .
H24 H 0.8595 0.1586 0.2403 0.089 Uiso 1 1 calc R . . . .
C25 C 0.8196(4) 0.2836(4) 0.3182(3) 0.0609(13) Uani 1 1 d . . . . .
H25 H 0.7545 0.2482 0.3415 0.073 Uiso 1 1 calc R . . . .


_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 C17 1.179(5) . ?
O2 C17 1.338(5) . ?
O2 C18 1.460(5) . ?
O3 C14 1.197(5) . ?
O4 C14 1.313(5) . ?
O4 C15 1.462(5) . ?
N1 H1 0.89(4) . ?
N1 C7 1.384(5) . ?
N1 C8 1.468(5) . ?
N2 C9 1.470(5) . ?
N2 C10 1.275(5) . ?
N3 C11 1.276(4) . ?
N3 C12 1.477(5) . ?
C1 C2 1.517(5) . ?
C1 C8 1.571(5) . ?
C1 C11 1.515(5) . ?
C1 C13 1.539(5) . ?
C2 C3 1.372(5) . ?
C2 C7 1.380(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.391(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.388(6) . ?
C8 H8 0.9800 . ?
C8 C9 1.559(5) . ?
C9 C14 1.536(6) . ?
C9 C17 1.538(5) . ?
C10 C11 1.482(5) . ?
C10 C20 1.484(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.533(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.477(7) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.280(9) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.399(6) . ?
C20 C25 1.372(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.378(7) . ?
C22 H22 0.9300 . ?
C22 C23 1.376(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.370(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.369(6) . ?
C25 H25 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
C17 O2 C18 118.0(4) . . ?
C14 O4 C15 116.0(3) . . ?
C7 N1 H1 116(3) . . ?
C7 N1 C8 110.2(3) . . ?
C8 N1 H1 117(3) . . ?
C10 N2 C9 119.3(3) . . ?
C11 N3 C12 108.0(3) . . ?
C2 C1 C8 102.7(3) . . ?
C2 C1 C13 114.6(3) . . ?
C11 C1 C2 110.2(3) . . ?
C11 C1 C8 112.1(3) . . ?
C11 C1 C13 100.2(3) . . ?
C13 C1 C8 117.3(3) . . ?
C3 C2 C1 129.7(3) . . ?
C3 C2 C7 120.8(4) . . ?
C7 C2 C1 109.5(3) . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(4) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(5) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.7(5) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 120.9 . . ?
C7 C6 C5 118.3(4) . . ?
C7 C6 H6 120.9 . . ?
N1 C7 C6 127.1(4) . . ?
C2 C7 N1 112.1(3) . . ?
C2 C7 C6 120.8(4) . . ?
N1 C8 C1 105.2(3) . . ?
N1 C8 H8 110.0 . . ?
N1 C8 C9 109.2(3) . . ?
C1 C8 H8 110.0 . . ?
C9 C8 C1 112.3(3) . . ?
C9 C8 H8 110.0 . . ?
N2 C9 C8 115.3(3) . . ?
N2 C9 C14 105.8(3) . . ?
N2 C9 C17 107.4(3) . . ?
C14 C9 C8 113.9(3) . . ?
C14 C9 C17 105.5(3) . . ?
C17 C9 C8 108.4(3) . . ?
N2 C10 C11 119.8(3) . . ?
N2 C10 C20 119.0(4) . . ?
C11 C10 C20 121.2(3) . . ?
N3 C11 C1 116.6(3) . . ?
N3 C11 C10 126.7(3) . . ?
C10 C11 C1 116.7(3) . . ?
N3 C12 H12A 110.4 . . ?
N3 C12 H12B 110.4 . . ?
N3 C12 C13 106.9(3) . . ?
H12A C12 H12B 108.6 . . ?
C13 C12 H12A 110.4 . . ?
C13 C12 H12B 110.4 . . ?
C1 C13 H13A 111.1 . . ?
C1 C13 H13B 111.1 . . ?
C12 C13 C1 103.5(3) . . ?
C12 C13 H13A 111.1 . . ?
C12 C13 H13B 111.1 . . ?
H13A C13 H13B 109.0 . . ?
O3 C14 O4 124.6(4) . . ?
O3 C14 C9 123.1(4) . . ?
O4 C14 C9 112.1(3) . . ?
O4 C15 H15A 110.1 . . ?
O4 C15 H15B 110.1 . . ?
O4 C15 C16 108.1(4) . . ?
H15A C15 H15B 108.4 . . ?
C16 C15 H15A 110.1 . . ?
C16 C15 H15B 110.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C17 O2 124.3(4) . . ?
O1 C17 C9 126.9(4) . . ?
O2 C17 C9 108.8(4) . . ?
O2 C18 H18A 109.0 . . ?
O2 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 O2 112.8(6) . . ?
C19 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C10 119.5(4) . . ?
C25 C20 C10 122.8(4) . . ?
C25 C20 C21 117.6(4) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.7(5) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.2(5) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 120.3 . . ?
C24 C23 C22 119.4(5) . . ?
C24 C23 H23 120.3 . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.4(5) . . ?
C25 C24 H24 119.8 . . ?
C20 C25 H25 119.1 . . ?
C24 C25 C20 121.7(5) . . ?
C24 C25 H25 119.1 . . ?

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
N1 C8 C9 N2 -80.0(4) . . . . ?
N1 C8 C9 C14 157.4(3) . . . . ?
N1 C8 C9 C17 40.3(4) . . . . ?
N2 C9 C14 O3 84.4(4) . . . . ?
N2 C9 C14 O4 -91.2(4) . . . . ?
N2 C9 C17 O1 0.3(7) . . . . ?
N2 C9 C17 O2 -179.8(3) . . . . ?
N2 C10 C11 N3 -141.7(4) . . . . ?
N2 C10 C11 C1 38.2(5) . . . . ?
N2 C10 C20 C21 7.8(6) . . . . ?
N2 C10 C20 C25 -169.8(4) . . . . ?
N3 C12 C13 C1 20.3(4) . . . . ?
C1 C2 C3 C4 176.4(4) . . . . ?
C1 C2 C7 N1 5.2(5) . . . . ?
C1 C2 C7 C6 -176.1(4) . . . . ?
C1 C8 C9 N2 36.3(4) . . . . ?
C1 C8 C9 C14 -86.3(4) . . . . ?
C1 C8 C9 C17 156.6(3) . . . . ?
C2 C1 C8 N1 3.1(4) . . . . ?
C2 C1 C8 C9 -115.6(3) . . . . ?
C2 C1 C11 N3 -105.1(4) . . . . ?
C2 C1 C11 C10 74.9(4) . . . . ?
C2 C1 C13 C12 97.4(4) . . . . ?
C2 C3 C4 C5 -0.2(7) . . . . ?
C3 C2 C7 N1 -176.9(4) . . . . ?
C3 C2 C7 C6 1.8(6) . . . . ?
C3 C4 C5 C6 0.8(7) . . . . ?
C4 C5 C6 C7 -0.1(7) . . . . ?
C5 C6 C7 N1 177.3(4) . . . . ?
C5 C6 C7 C2 -1.2(6) . . . . ?
C7 N1 C8 C1 -0.3(4) . . . . ?
C7 N1 C8 C9 120.5(3) . . . . ?
C7 C2 C3 C4 -1.1(6) . . . . ?
C8 N1 C7 C2 -3.0(5) . . . . ?
C8 N1 C7 C6 178.3(4) . . . . ?
C8 C1 C2 C3 177.4(4) . . . . ?
C8 C1 C2 C7 -4.9(4) . . . . ?
C8 C1 C11 N3 141.2(4) . . . . ?
C8 C1 C11 C10 -38.8(5) . . . . ?
C8 C1 C13 C12 -141.9(4) . . . . ?
C8 C9 C14 O3 -147.9(4) . . . . ?
C8 C9 C14 O4 36.5(4) . . . . ?
C8 C9 C17 O1 -124.9(5) . . . . ?
C8 C9 C17 O2 55.0(5) . . . . ?
C9 N2 C10 C11 4.6(5) . . . . ?
C9 N2 C10 C20 -178.3(3) . . . . ?
C10 N2 C9 C8 -42.6(5) . . . . ?
C10 N2 C9 C14 84.2(4) . . . . ?
C10 N2 C9 C17 -163.6(4) . . . . ?
C10 C20 C21 C22 -177.6(4) . . . . ?
C10 C20 C25 C24 176.7(5) . . . . ?
C11 N3 C12 C13 -11.2(5) . . . . ?
C11 C1 C2 C3 57.8(5) . . . . ?
C11 C1 C2 C7 -124.5(3) . . . . ?
C11 C1 C8 N1 121.3(3) . . . . ?
C11 C1 C8 C9 2.6(5) . . . . ?
C11 C1 C13 C12 -20.4(4) . . . . ?
C11 C10 C20 C21 -175.1(4) . . . . ?
C11 C10 C20 C25 7.3(6) . . . . ?
C12 N3 C11 C1 -3.4(5) . . . . ?
C12 N3 C11 C10 176.5(4) . . . . ?
C13 C1 C2 C3 -54.3(5) . . . . ?
C13 C1 C2 C7 123.4(4) . . . . ?
C13 C1 C8 N1 -123.6(3) . . . . ?
C13 C1 C8 C9 117.7(4) . . . . ?
C13 C1 C11 N3 16.0(4) . . . . ?
C13 C1 C11 C10 -163.9(3) . . . . ?
C14 O4 C15 C16 -174.9(4) . . . . ?
C14 C9 C17 O1 112.8(6) . . . . ?
C14 C9 C17 O2 -67.3(4) . . . . ?
C15 O4 C14 O3 -3.1(6) . . . . ?
C15 O4 C14 C9 172.5(3) . . . . ?
C17 O2 C18 C19 102.8(9) . . . . ?
C17 C9 C14 O3 -29.2(5) . . . . ?
C17 C9 C14 O4 155.2(3) . . . . ?
C18 O2 C17 O1 -5.9(7) . . . . ?
C18 O2 C17 C9 174.1(4) . . . . ?
C20 C10 C11 N3 41.2(6) . . . . ?
C20 C10 C11 C1 -138.9(4) . . . . ?
C20 C21 C22 C23 1.5(8) . . . . ?
C21 C20 C25 C24 -0.9(7) . . . . ?
C21 C22 C23 C24 -2.2(8) . . . . ?
C22 C23 C24 C25 1.3(8) . . . . ?
C23 C24 C25 C20 0.2(8) . . . . ?
C25 C20 C21 C22 0.0(7) . . . . ?

_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_210818_s1_lgg
_database_code_depnum_ccdc_archive 'CCDC 2104294'
loop_
_audit_author_name
_audit_author_address
'hai zhen Li'
;CCDC
China
;
_audit_update_record             
;
2021-09-17 deposited with the CCDC.	2021-09-29 downloaded from the CCDC.
;
_audit_creation_date             2021-09-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C29 H31 N3 O6'
_chemical_formula_sum            'C29 H31 N3 O6'
_chemical_formula_weight         517.57
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   15.8169(18)
_cell_length_b                   16.0922(13)
_cell_length_c                   23.146(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.329(13)
_cell_angle_gamma                90
_cell_volume                     5681.8(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2666
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.2980
_cell_measurement_theta_min      3.3320
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2192
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13458
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.016
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   21.20   0.7000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -99.0000 -120.0000 66

#__ type_ start__ end____ width___ exp.time_
  2 omega  -52.00   33.40   0.7000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       17.5086  -38.0000   90.0000 122

#__ type_ start__ end____ width___ exp.time_
  3 omega  -12.00   88.10   0.7000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       17.5086   19.0000   90.0000 143
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0444282000
_diffrn_orient_matrix_UB_12      -0.0039733000
_diffrn_orient_matrix_UB_13      -0.0005497000
_diffrn_orient_matrix_UB_21      0.0134660000
_diffrn_orient_matrix_UB_22      0.0057305000
_diffrn_orient_matrix_UB_23      0.0315051000
_diffrn_orient_matrix_UB_31      -0.0022501000
_diffrn_orient_matrix_UB_32      -0.0435164000
_diffrn_orient_matrix_UB_33      0.0042054000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3381
_reflns_number_total             5791
_reflns_odcompleteness_completeness 99.73
_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, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         5791
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0639
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0884P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1670
_refine_ls_wR_factor_ref         0.1906
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2. Restrained distances
 C28-O6 = C28-C29 = C28-C29A = C25-C26A
 1.55 with sigma of 0.02
 H29B-H29F
 1.37 with sigma of 0.02
 H29C-H29E
 1.2 with sigma of 0.02
 H26A-H26D
 1.64 with sigma of 0.02
 H25B-H26F
 1.38 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C29) = Uanis(C29A)
Uanis(C26) = Uanis(C26A)
Uanis(C26A) = Uanis(C26) = Uanis(C29A) = Uanis(C29)
4. Others
 Sof(H28C)=Sof(H28D)=Sof(C29A)=Sof(H29D)=Sof(H29E)=Sof(H29F)=1-FVAR(1)
 Sof(H28A)=Sof(H28B)=Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=FVAR(1)
 Sof(H25C)=Sof(H25D)=Sof(C26A)=Sof(H26D)=Sof(H26E)=Sof(H26F)=1-FVAR(2)
 Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C11(H11)
5.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C25(H25A,H25B), C25(H25C,H25D), C28(H28A,H28B),
 C28(H28C,H28D)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C19(H19), C20(H20), C21(H21), C22(H22),
 C23(H23)
5.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C26(H26A,H26B,H26C), C29(H29A,H29B,
 H29C), C29A(H29D,H29E,H29F), C26A(H26D,H26E,H26F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.44086(16) 0.10898(14) 0.49737(9) 0.0788(7) Uani 1 1 d . . . . .
O2 O 0.51574(19) -0.02184(13) 0.16467(9) 0.0887(8) Uani 1 1 d . . . . .
O3 O 0.31540(14) -0.05950(12) 0.28098(10) 0.0718(6) Uani 1 1 d . . . . .
O4 O 0.30232(15) 0.01846(13) 0.19995(9) 0.0733(6) Uani 1 1 d . . . . .
O5 O 0.24349(14) 0.10548(14) 0.31028(12) 0.0825(7) Uani 1 1 d . . . . .
O6 O 0.34050(13) 0.20755(12) 0.32148(10) 0.0638(6) Uani 1 1 d D . . . .
N1 N 0.45670(13) 0.09220(12) 0.40419(9) 0.0411(5) Uani 1 1 d . . . . .
N2 N 0.52658(14) -0.04623(11) 0.26108(9) 0.0415(5) Uani 1 1 d . . . . .
N3 N 0.41919(12) 0.12655(11) 0.25119(8) 0.0367(5) Uani 1 1 d . . . . .
C1 C 0.58709(16) 0.11326(15) 0.38072(10) 0.0405(6) Uani 1 1 d . . . . .
C2 C 0.66602(17) 0.15165(17) 0.38365(12) 0.0510(7) Uani 1 1 d . . . . .
H2 H 0.703073 0.131340 0.361730 0.061 Uiso 1 1 calc R . . . .
C3 C 0.6891(2) 0.2209(2) 0.41973(13) 0.0648(8) Uani 1 1 d . . . . .
H3 H 0.742088 0.247513 0.422073 0.078 Uiso 1 1 calc R . . . .
C4 C 0.6344(2) 0.25049(19) 0.45211(13) 0.0640(8) Uani 1 1 d . . . . .
H4 H 0.650473 0.297622 0.475706 0.077 Uiso 1 1 calc R . . . .
C5 C 0.55528(19) 0.21140(17) 0.45033(11) 0.0531(7) Uani 1 1 d . . . . .
H5 H 0.518692 0.231110 0.472786 0.064 Uiso 1 1 calc R . . . .
C6 C 0.53304(16) 0.14263(15) 0.41422(11) 0.0417(6) Uani 1 1 d . . . . .
C7 C 0.45001(15) 0.04163(14) 0.34978(10) 0.0362(5) Uani 1 1 d . . . . .
H7 H 0.431857 -0.014728 0.357197 0.043 Uiso 1 1 calc R . . . .
C8 C 0.54601(15) 0.03820(14) 0.34447(10) 0.0374(6) Uani 1 1 d . . . . .
C9 C 0.58552(17) -0.04651(15) 0.36551(11) 0.0460(6) Uani 1 1 d . . . . .
H9A H 0.648860 -0.045526 0.373328 0.055 Uiso 1 1 calc R . . . .
H9B H 0.570037 -0.064178 0.401455 0.055 Uiso 1 1 calc R . . . .
C10 C 0.54471(18) -0.10255(15) 0.31324(11) 0.0483(7) Uani 1 1 d . . . . .
H10A H 0.584914 -0.146349 0.309224 0.058 Uiso 1 1 calc R . . . .
H10B H 0.491062 -0.127452 0.317914 0.058 Uiso 1 1 calc R . . . .
C11 C 0.55148(15) 0.03966(13) 0.27980(10) 0.0357(6) Uani 1 1 d . . . . .
H11 H 0.612398 0.049201 0.279111 0.043 Uiso 1 1 calc R . . . .
C12 C 0.49361(15) 0.10683(13) 0.24341(10) 0.0353(5) Uani 1 1 d . . . . .
C13 C 0.38281(15) 0.07685(14) 0.29193(10) 0.0371(6) Uani 1 1 d . . . . .
C14 C 0.41940(19) 0.07129(17) 0.44960(13) 0.0521(7) Uani 1 1 d . . . . .
C15 C 0.3538(2) 0.00174(19) 0.43899(14) 0.0676(9) Uani 1 1 d . . . . .
H15A H 0.313379 0.008153 0.400221 0.101 Uiso 1 1 calc GR . . . .
H15B H 0.322345 0.003048 0.469218 0.101 Uiso 1 1 calc GR . . . .
H15C H 0.383771 -0.050464 0.440764 0.101 Uiso 1 1 calc GR . . . .
C16 C 0.5130(2) -0.07137(16) 0.20396(13) 0.0549(7) Uani 1 1 d . . . . .
C17 C 0.4941(3) -0.16131(18) 0.19171(16) 0.0818(11) Uani 1 1 d . . . . .
H17A H 0.547658 -0.192405 0.203861 0.123 Uiso 1 1 calc GR . . . .
H17B H 0.468257 -0.169302 0.149631 0.123 Uiso 1 1 calc GR . . . .
H17C H 0.454143 -0.180181 0.213740 0.123 Uiso 1 1 calc GR . . . .
C18 C 0.52529(16) 0.15794(13) 0.20009(10) 0.0359(6) Uani 1 1 d . . . . .
C19 C 0.60944(18) 0.18801(15) 0.21232(13) 0.0511(7) Uani 1 1 d . . . . .
H19 H 0.649283 0.174511 0.248446 0.061 Uiso 1 1 calc R . . . .
C20 C 0.6357(2) 0.23785(17) 0.17189(15) 0.0615(8) Uani 1 1 d . . . . .
H20 H 0.692472 0.258823 0.181158 0.074 Uiso 1 1 calc R . . . .
C21 C 0.5775(2) 0.25665(17) 0.11755(14) 0.0629(9) Uani 1 1 d . . . . .
H21 H 0.595546 0.289259 0.089836 0.075 Uiso 1 1 calc R . . . .
C22 C 0.4941(2) 0.22754(17) 0.10461(13) 0.0646(8) Uani 1 1 d . . . . .
H22 H 0.454827 0.240511 0.068138 0.078 Uiso 1 1 calc R . . . .
C23 C 0.46749(19) 0.17840(16) 0.14582(12) 0.0534(7) Uani 1 1 d . . . . .
H23 H 0.410111 0.158991 0.136871 0.064 Uiso 1 1 calc R . . . .
C24 C 0.33040(17) 0.00284(17) 0.25729(13) 0.0489(7) Uani 1 1 d . . . . .
C25 C 0.2493(3) -0.0456(3) 0.16206(19) 0.1151(16) Uani 1 1 d D . . . .
H25A H 0.267025 -0.100214 0.178594 0.138 Uiso 0.664(8) 1 calc R . P A 1
H25B H 0.187901 -0.037784 0.160359 0.138 Uiso 0.664(8) 1 calc DR . P A 1
H25C H 0.202978 -0.064148 0.179319 0.138 Uiso 0.336(8) 1 calc R . P A 2
H25D H 0.285544 -0.093044 0.158711 0.138 Uiso 0.336(8) 1 calc R . P A 2
C26 C 0.2620(6) -0.0392(5) 0.1025(3) 0.128(2) Uani 0.664(8) 1 d . . P A 1
H26A H 0.224966 -0.078619 0.076555 0.192 Uiso 0.664(8) 1 calc DGR . P A 1
H26B H 0.322209 -0.050639 0.104210 0.192 Uiso 0.664(8) 1 calc GR . P A 1
H26C H 0.247378 0.015960 0.087342 0.192 Uiso 0.664(8) 1 calc GR . P A 1
C27 C 0.31368(17) 0.13156(17) 0.30906(11) 0.0462(6) Uani 1 1 d . . . . .
C28 C 0.2805(2) 0.2656(2) 0.33945(16) 0.0844(11) Uani 1 1 d D . . . .
H28A H 0.221469 0.257038 0.314354 0.101 Uiso 0.71(2) 1 calc R . P B 1
H28B H 0.297625 0.322168 0.333623 0.101 Uiso 0.71(2) 1 calc R . P B 1
H28C H 0.223002 0.240251 0.332430 0.101 Uiso 0.29(2) 1 calc R . P B 2
H28D H 0.274694 0.315520 0.315270 0.101 Uiso 0.29(2) 1 calc R . P B 2
C29 C 0.2815(9) 0.2534(8) 0.4026(4) 0.128(2) Uani 0.71(2) 1 d D . P B 1
H29A H 0.251328 0.202888 0.406634 0.192 Uiso 0.71(2) 1 calc GR . P B 1
H29B H 0.252900 0.299434 0.415899 0.192 Uiso 0.71(2) 1 calc DGR . P B 1
H29C H 0.341100 0.250004 0.426586 0.192 Uiso 0.71(2) 1 calc DGR . P B 1
C29A C 0.314(2) 0.288(2) 0.4052(7) 0.128(2) Uani 0.29(2) 1 d D . P B 2
H29D H 0.335234 0.239196 0.428050 0.192 Uiso 0.29(2) 1 calc GR . P B 2
H29E H 0.267381 0.312219 0.418970 0.192 Uiso 0.29(2) 1 calc DGR . P B 2
H29F H 0.361003 0.327727 0.410113 0.192 Uiso 0.29(2) 1 calc DGR . P B 2
C26A C 0.2114(12) -0.0084(10) 0.1023(6) 0.128(2) Uani 0.336(8) 1 d D . P A 2
H26D H 0.159562 -0.038523 0.082172 0.192 Uiso 0.336(8) 1 calc DGR . P A 2
H26E H 0.253455 -0.011305 0.079128 0.192 Uiso 0.336(8) 1 calc GR . P A 2
H26F H 0.196557 0.048581 0.106897 0.192 Uiso 0.336(8) 1 calc DGR . 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 C14 1.228(3) . ?
O2 C16 1.219(3) . ?
O3 C24 1.197(3) . ?
O4 C24 1.308(3) . ?
O4 C25 1.465(4) . ?
O5 C27 1.194(3) . ?
O6 C27 1.301(3) . ?
O6 C28 1.468(3) . ?
N1 C6 1.422(3) . ?
N1 C7 1.480(3) . ?
N1 C14 1.376(3) . ?
N2 C10 1.476(3) . ?
N2 C11 1.471(3) . ?
N2 C16 1.345(3) . ?
N3 C12 1.277(3) . ?
N3 C13 1.465(3) . ?
C1 C2 1.378(3) . ?
C1 C6 1.381(3) . ?
C1 C8 1.516(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.391(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.375(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.556(3) . ?
C7 C13 1.578(3) . ?
C8 C9 1.525(3) . ?
C8 C11 1.522(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.510(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11 0.9800 . ?
C11 C12 1.519(3) . ?
C12 C18 1.483(3) . ?
C13 C24 1.548(4) . ?
C13 C27 1.535(3) . ?
C14 C15 1.502(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.490(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.374(3) . ?
C18 C23 1.384(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.377(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.381(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.357(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.388(4) . ?
C23 H23 0.9300 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 H25C 0.9700 . ?
C25 H25D 0.9700 . ?
C25 C26 1.448(8) . ?
C25 C26A 1.480(13) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 H28C 0.9700 . ?
C28 H28D 0.9700 . ?
C28 C29 1.471(8) . ?
C28 C29A 1.518(15) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C29A H29D 0.9600 . ?
C29A H29E 0.9600 . ?
C29A H29F 0.9600 . ?
C26A H26D 0.9600 . ?
C26A H26E 0.9600 . ?
C26A H26F 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
C24 O4 C25 117.4(2) . . ?
C27 O6 C28 117.6(2) . . ?
C6 N1 C7 108.63(17) . . ?
C14 N1 C6 122.1(2) . . ?
C14 N1 C7 124.5(2) . . ?
C11 N2 C10 110.92(19) . . ?
C16 N2 C10 124.4(2) . . ?
C16 N2 C11 122.2(2) . . ?
C12 N3 C13 119.24(19) . . ?
C2 C1 C6 120.4(2) . . ?
C2 C1 C8 129.4(2) . . ?
C6 C1 C8 110.2(2) . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.8(3) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.3(3) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 121.1 . . ?
C6 C5 C4 117.7(3) . . ?
C6 C5 H5 121.1 . . ?
C1 C6 N1 109.8(2) . . ?
C5 C6 N1 128.9(2) . . ?
C5 C6 C1 121.3(2) . . ?
N1 C7 H7 108.6 . . ?
N1 C7 C8 103.59(18) . . ?
N1 C7 C13 113.90(18) . . ?
C8 C7 H7 108.6 . . ?
C8 C7 C13 113.45(17) . . ?
C13 C7 H7 108.6 . . ?
C1 C8 C7 102.27(18) . . ?
C1 C8 C9 117.1(2) . . ?
C1 C8 C11 113.87(18) . . ?
C9 C8 C7 109.42(18) . . ?
C11 C8 C7 112.8(2) . . ?
C11 C8 C9 101.70(18) . . ?
C8 C9 H9A 111.2 . . ?
C8 C9 H9B 111.2 . . ?
H9A C9 H9B 109.1 . . ?
C10 C9 C8 103.0(2) . . ?
C10 C9 H9A 111.2 . . ?
C10 C9 H9B 111.2 . . ?
N2 C10 C9 103.77(19) . . ?
N2 C10 H10A 111.0 . . ?
N2 C10 H10B 111.0 . . ?
C9 C10 H10A 111.0 . . ?
C9 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
N2 C11 C8 101.24(17) . . ?
N2 C11 H11 109.3 . . ?
N2 C11 C12 115.48(19) . . ?
C8 C11 H11 109.3 . . ?
C12 C11 C8 111.94(18) . . ?
C12 C11 H11 109.3 . . ?
N3 C12 C11 122.8(2) . . ?
N3 C12 C18 116.5(2) . . ?
C18 C12 C11 120.5(2) . . ?
N3 C13 C7 116.81(18) . . ?
N3 C13 C24 109.52(19) . . ?
N3 C13 C27 106.31(19) . . ?
C24 C13 C7 108.14(19) . . ?
C27 C13 C7 110.66(19) . . ?
C27 C13 C24 104.7(2) . . ?
O1 C14 N1 119.7(3) . . ?
O1 C14 C15 122.0(2) . . ?
N1 C14 C15 118.3(2) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 N2 120.6(2) . . ?
O2 C16 C17 122.6(3) . . ?
N2 C16 C17 116.8(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C12 122.6(2) . . ?
C19 C18 C23 118.4(2) . . ?
C23 C18 C12 119.1(2) . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 121.0(3) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.9(3) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.0(3) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 119.9(3) . . ?
C23 C22 H22 120.0 . . ?
C18 C23 C22 120.8(3) . . ?
C18 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
O3 C24 O4 124.8(3) . . ?
O3 C24 C13 123.5(3) . . ?
O4 C24 C13 111.7(2) . . ?
O4 C25 H25A 110.0 . . ?
O4 C25 H25B 110.0 . . ?
O4 C25 H25C 110.2 . . ?
O4 C25 H25D 110.2 . . ?
O4 C25 C26A 107.6(7) . . ?
H25A C25 H25B 108.4 . . ?
H25C C25 H25D 108.5 . . ?
C26 C25 O4 108.6(4) . . ?
C26 C25 H25A 110.0 . . ?
C26 C25 H25B 110.0 . . ?
C26A C25 H25C 110.2 . . ?
C26A C25 H25D 110.2 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O5 C27 O6 125.2(3) . . ?
O5 C27 C13 122.3(3) . . ?
O6 C27 C13 112.5(2) . . ?
O6 C28 H28A 109.4 . . ?
O6 C28 H28B 109.4 . . ?
O6 C28 H28C 109.5 . . ?
O6 C28 H28D 109.5 . . ?
O6 C28 C29 111.0(4) . . ?
O6 C28 C29A 110.8(10) . . ?
H28A C28 H28B 108.0 . . ?
H28C C28 H28D 108.1 . . ?
C29 C28 H28A 109.4 . . ?
C29 C28 H28B 109.4 . . ?
C29A C28 H28C 109.5 . . ?
C29A C28 H28D 109.5 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C29A H29D 109.5 . . ?
C28 C29A H29E 109.5 . . ?
C28 C29A H29F 109.5 . . ?
H29D C29A H29E 109.5 . . ?
H29D C29A H29F 109.5 . . ?
H29E C29A H29F 109.5 . . ?
C25 C26A H26D 109.5 . . ?
C25 C26A H26E 109.5 . . ?
C25 C26A H26F 109.5 . . ?
H26D C26A H26E 109.5 . . ?
H26D C26A H26F 109.5 . . ?
H26E C26A H26F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C7 C8 C1 -21.6(2) . . . . ?
N1 C7 C8 C9 103.3(2) . . . . ?
N1 C7 C8 C11 -144.29(18) . . . . ?
N1 C7 C13 N3 98.0(2) . . . . ?
N1 C7 C13 C24 -138.01(19) . . . . ?
N1 C7 C13 C27 -23.8(3) . . . . ?
N2 C11 C12 N3 79.2(3) . . . . ?
N2 C11 C12 C18 -106.1(2) . . . . ?
N3 C12 C18 C19 133.8(2) . . . . ?
N3 C12 C18 C23 -44.3(3) . . . . ?
N3 C13 C24 O3 157.7(3) . . . . ?
N3 C13 C24 O4 -24.7(3) . . . . ?
N3 C13 C27 O5 135.9(3) . . . . ?
N3 C13 C27 O6 -43.9(3) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C1 C8 C9 C10 -167.49(19) . . . . ?
C1 C8 C11 N2 167.44(19) . . . . ?
C1 C8 C11 C12 -69.0(3) . . . . ?
C2 C1 C6 N1 -179.2(2) . . . . ?
C2 C1 C6 C5 1.3(4) . . . . ?
C2 C1 C8 C7 -166.8(2) . . . . ?
C2 C1 C8 C9 73.6(3) . . . . ?
C2 C1 C8 C11 -44.8(3) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C3 C4 C5 C6 -1.0(4) . . . . ?
C4 C5 C6 N1 -179.6(2) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C6 N1 C7 C8 23.3(2) . . . . ?
C6 N1 C7 C13 -100.4(2) . . . . ?
C6 N1 C14 O1 14.4(4) . . . . ?
C6 N1 C14 C15 -164.9(2) . . . . ?
C6 C1 C2 C3 -1.3(4) . . . . ?
C6 C1 C8 C7 13.5(2) . . . . ?
C6 C1 C8 C9 -106.1(2) . . . . ?
C6 C1 C8 C11 135.5(2) . . . . ?
C7 N1 C6 C1 -15.6(3) . . . . ?
C7 N1 C6 C5 163.9(2) . . . . ?
C7 N1 C14 O1 167.3(2) . . . . ?
C7 N1 C14 C15 -12.1(4) . . . . ?
C7 C8 C9 C10 76.8(2) . . . . ?
C7 C8 C11 N2 -76.6(2) . . . . ?
C7 C8 C11 C12 47.0(3) . . . . ?
C7 C13 C24 O3 29.4(3) . . . . ?
C7 C13 C24 O4 -153.0(2) . . . . ?
C7 C13 C27 O5 -96.3(3) . . . . ?
C7 C13 C27 O6 83.9(2) . . . . ?
C8 C1 C2 C3 179.0(2) . . . . ?
C8 C1 C6 N1 0.6(3) . . . . ?
C8 C1 C6 C5 -179.0(2) . . . . ?
C8 C7 C13 N3 -20.2(3) . . . . ?
C8 C7 C13 C24 103.8(2) . . . . ?
C8 C7 C13 C27 -142.0(2) . . . . ?
C8 C9 C10 N2 27.6(2) . . . . ?
C8 C11 C12 N3 -36.0(3) . . . . ?
C8 C11 C12 C18 138.8(2) . . . . ?
C9 C8 C11 N2 40.5(2) . . . . ?
C9 C8 C11 C12 164.06(19) . . . . ?
C10 N2 C11 C8 -24.4(2) . . . . ?
C10 N2 C11 C12 -145.5(2) . . . . ?
C10 N2 C16 O2 -165.3(3) . . . . ?
C10 N2 C16 C17 15.1(4) . . . . ?
C11 N2 C10 C9 -1.9(3) . . . . ?
C11 N2 C16 O2 -4.5(4) . . . . ?
C11 N2 C16 C17 175.9(2) . . . . ?
C11 C8 C9 C10 -42.7(2) . . . . ?
C11 C12 C18 C19 -41.2(3) . . . . ?
C11 C12 C18 C23 140.7(2) . . . . ?
C12 N3 C13 C7 36.1(3) . . . . ?
C12 N3 C13 C24 -87.2(3) . . . . ?
C12 N3 C13 C27 160.2(2) . . . . ?
C12 C18 C19 C20 -177.6(2) . . . . ?
C12 C18 C23 C22 178.7(2) . . . . ?
C13 N3 C12 C11 -7.0(3) . . . . ?
C13 N3 C12 C18 178.02(19) . . . . ?
C13 C7 C8 C1 102.4(2) . . . . ?
C13 C7 C8 C9 -132.7(2) . . . . ?
C13 C7 C8 C11 -20.3(3) . . . . ?
C14 N1 C6 C1 141.0(2) . . . . ?
C14 N1 C6 C5 -39.4(4) . . . . ?
C14 N1 C7 C8 -132.7(2) . . . . ?
C14 N1 C7 C13 103.6(3) . . . . ?
C16 N2 C10 C9 160.8(2) . . . . ?
C16 N2 C11 C8 172.5(2) . . . . ?
C16 N2 C11 C12 51.4(3) . . . . ?
C18 C19 C20 C21 -1.5(4) . . . . ?
C19 C18 C23 C22 0.5(4) . . . . ?
C19 C20 C21 C22 1.5(4) . . . . ?
C20 C21 C22 C23 -0.5(4) . . . . ?
C21 C22 C23 C18 -0.5(4) . . . . ?
C23 C18 C19 C20 0.5(4) . . . . ?
C24 O4 C25 C26 -151.2(5) . . . . ?
C24 O4 C25 C26A 169.3(8) . . . . ?
C24 C13 C27 O5 20.0(3) . . . . ?
C24 C13 C27 O6 -159.8(2) . . . . ?
C25 O4 C24 O3 -0.6(5) . . . . ?
C25 O4 C24 C13 -178.2(3) . . . . ?
C27 O6 C28 C29 79.3(8) . . . . ?
C27 O6 C28 C29A 110.5(18) . . . . ?
C27 C13 C24 O3 -88.7(3) . . . . ?
C27 C13 C24 O4 89.0(3) . . . . ?
C28 O6 C27 O5 1.1(4) . . . . ?
C28 O6 C27 C13 -179.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
