# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_080511e
_database_code_depnum_ccdc_archive 'CCDC 2168507'
loop_
_audit_author_name
_audit_author_address
'Liping Wang'
;Guizhou Medcial University
China
;
_audit_update_record             
;
2022-04-25 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;
_audit_creation_date             2022-03-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C36 H29 I N4 O6'
_chemical_formula_sum            'C36 H29 I N4 O6'
_chemical_formula_weight         740.53
_chemical_absolute_configuration ad
_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'
I I -0.4742 1.8119 '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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   32.092(3)
_cell_length_b                   6.9177(9)
_cell_length_c                   17.3064(17)
_cell_angle_alpha                90
_cell_angle_beta                 98.106(2)
_cell_angle_gamma                90
_cell_volume                     3803.6(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2597
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.206
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.878
_shelx_estimated_absorpt_T_min   0.747
_exptl_absorpt_coefficient_mu    0.887
_exptl_absorpt_correction_T_max  0.8784
_exptl_absorpt_correction_T_min  0.7465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0710
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9708
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         1.621
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    0.897
_reflns_Friedel_fraction_max     0.897
_reflns_number_gt                3734
_reflns_number_total             6391
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 1202 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.862
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     412
_refine_ls_number_reflns         6391
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      0.862
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0582P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1136
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.00001 and sigma for 1-3 distances of 0.00001
3.a Ternary CH refined with riding coordinates:
 C29(H29), C31(H31), C32(H32), C33(H33)
3.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C30(H30A,H30B), C34(H34A,H34B)
3.c Me refined with riding coordinates:
 C36(H36A,H36B,H36C)
3.d Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
3.e Fitted hexagon refined as free rotating group:
 C23(C24,C25,C26,C27,C28)
;
_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
I1 I 0.36640(2) 0.61958(13) 0.74027(3) 0.0994(3) Uani 1 1 d . . . . .
N1 N 0.20211(19) 0.7596(10) 0.7391(3) 0.0592(17) Uani 1 1 d . . . . .
N2 N 0.28128(18) 0.7461(8) 0.8711(3) 0.0488(14) Uani 1 1 d . . . . .
H2 H 0.291726 0.744971 0.827992 0.059 Uiso 1 1 calc R U . . .
N3 N 0.1353(2) 0.7256(9) 1.0382(3) 0.0585(17) Uani 1 1 d . . . . .
N4 N 0.2556(2) 1.2486(9) 0.6133(3) 0.0574(16) Uani 1 1 d . . . . .
O1 O 0.19819(16) 0.7478(8) 1.1192(3) 0.0659(14) Uani 1 1 d . . . . .
O2 O 0.08457(18) 0.6879(8) 0.9288(3) 0.078(2) Uani 1 1 d . . . . .
O3 O 0.08867(18) 0.8596(9) 1.1192(3) 0.0764(16) Uani 1 1 d . . . . .
O4 O 0.26963(15) 0.7628(7) 0.6998(3) 0.0502(12) Uani 1 1 d . . . . .
O5 O 0.32071(16) 1.1458(11) 0.6035(3) 0.0661(15) Uani 1 1 d . . . . .
O6 O 0.28609(19) 1.3224(9) 0.5043(3) 0.0833(18) Uani 1 1 d . . . . .
C1 C 0.2050(2) 0.7512(11) 0.8205(4) 0.0484(17) Uani 1 1 d . . . . .
C2 C 0.1644(2) 0.7368(12) 0.8400(4) 0.0539(19) Uani 1 1 d . . . . .
C3 C 0.1355(2) 0.7299(13) 0.7678(4) 0.065(2) Uani 1 1 d . . . . .
C4 C 0.1594(2) 0.7529(13) 0.7069(4) 0.065(2) Uani 1 1 d . . . . .
C5 C 0.1419(3) 0.7516(18) 0.6290(5) 0.094(3) Uani 1 1 d . . . . .
H5 H 0.158151 0.764684 0.588840 0.113 Uiso 1 1 calc R U . . .
C6 C 0.0998(4) 0.730(2) 0.6155(6) 0.128(5) Uani 1 1 d . . . . .
H6 H 0.087020 0.728217 0.563833 0.154 Uiso 1 1 calc R U . . .
C7 C 0.0737(3) 0.710(2) 0.6740(7) 0.133(6) Uani 1 1 d . . . . .
H7 H 0.044685 0.698348 0.660524 0.159 Uiso 1 1 calc R U . . .
C8 C 0.0915(3) 0.7092(15) 0.7516(5) 0.091(3) Uani 1 1 d . . . . .
H8 H 0.075072 0.695325 0.791412 0.110 Uiso 1 1 calc R U . . .
C9 C 0.2398(2) 0.7527(11) 0.8773(4) 0.0494(18) Uani 1 1 d . . . . .
C10 C 0.2347(2) 0.7557(10) 0.9581(4) 0.0435(16) Uani 1 1 d . . . . .
C11 C 0.2755(2) 0.7524(10) 1.0007(4) 0.0452(17) Uani 1 1 d . . . . .
C12 C 0.3042(2) 0.7415(10) 0.9445(4) 0.0487(18) Uani 1 1 d . . . . .
C13 C 0.3476(2) 0.7292(12) 0.9671(5) 0.060(2) Uani 1 1 d . . . . .
H13 H 0.365960 0.720457 0.930193 0.072 Uiso 1 1 calc R U . . .
C14 C 0.3622(3) 0.7306(12) 1.0452(5) 0.063(2) Uani 1 1 d . . . . .
H14 H 0.391055 0.720890 1.061248 0.076 Uiso 1 1 calc R U . . .
C15 C 0.3356(3) 0.7458(12) 1.1009(4) 0.061(2) Uani 1 1 d . . . . .
H15 H 0.346719 0.751380 1.153512 0.074 Uiso 1 1 calc R U . . .
C16 C 0.2920(2) 0.7529(11) 1.0789(4) 0.0548(19) Uani 1 1 d . . . . .
H16 H 0.274197 0.757989 1.116808 0.066 Uiso 1 1 calc R U . . .
C17 C 0.1792(3) 0.7412(11) 1.0543(4) 0.0515(18) Uani 1 1 d . . . . .
C18 C 0.1952(2) 0.7475(11) 0.9767(4) 0.0485(17) Uani 1 1 d . . . . .
C19 C 0.1599(2) 0.7334(11) 0.9193(4) 0.0539(19) Uani 1 1 d . . . . .
C20 C 0.1207(3) 0.7124(10) 0.9576(5) 0.057(2) Uani 1 1 d . . . . .
C21 C 0.1079(3) 0.6914(12) 1.0968(5) 0.076(3) Uani 1 1 d . . . . .
H21A H 0.086310 0.599555 1.076358 0.091 Uiso 1 1 calc R U . . .
H21B H 0.124271 0.633829 1.142453 0.091 Uiso 1 1 calc R U . . .
C22 C 0.0527(3) 0.9143(18) 1.0668(7) 0.104(4) Uani 1 1 d . . . . .
H22A H 0.035882 0.801208 1.050537 0.125 Uiso 1 1 calc R U . . .
H22B H 0.061234 0.974047 1.020834 0.125 Uiso 1 1 calc R U . . .
C23 C 0.0272(2) 1.0558(12) 1.1076(5) 0.086(3) Uani 1 1 d G . . . .
C24 C 0.0282(3) 1.2523(14) 1.0912(5) 0.152(6) Uani 1 1 d G . . . .
H24 H 0.045670 1.298323 1.056728 0.182 Uiso 1 1 calc R U . . .
C25 C 0.0032(4) 1.3801(11) 1.1263(7) 0.217(10) Uani 1 1 d G . . . .
H25 H 0.003922 1.511543 1.115331 0.260 Uiso 1 1 calc R U . . .
C26 C -0.0229(3) 1.3113(17) 1.1778(6) 0.159(6) Uani 1 1 d G . . . .
H26 H -0.039610 1.396815 1.201318 0.191 Uiso 1 1 calc R U . . .
C27 C -0.0239(3) 1.1149(19) 1.1942(5) 0.172(6) Uani 1 1 d G . . . .
H27 H -0.041395 1.068864 1.228702 0.207 Uiso 1 1 calc R U . . .
C28 C 0.0011(3) 0.9871(12) 1.1591(6) 0.142(5) Uani 1 1 d G . . . .
H28 H 0.000352 0.855640 1.170100 0.170 Uiso 1 1 calc R U . . .
C29 C 0.2314(2) 0.8717(11) 0.6986(4) 0.054(2) Uani 1 1 d . . . . .
H29 H 0.218671 0.886090 0.643962 0.065 Uiso 1 1 calc R U . . .
C30 C 0.2402(2) 1.0710(11) 0.7319(4) 0.056(2) Uani 1 1 d . . . . .
H30A H 0.250705 1.060333 0.787075 0.067 Uiso 1 1 calc R U . . .
H30B H 0.214122 1.143929 0.726678 0.067 Uiso 1 1 calc R U . . .
C31 C 0.2720(2) 1.1794(10) 0.6916(4) 0.055(2) Uani 1 1 d . . . . .
H31 H 0.283556 1.287932 0.724128 0.066 Uiso 1 1 calc R U . . .
C32 C 0.3081(2) 1.0509(10) 0.6706(4) 0.059(2) Uani 1 1 d . . . . .
H32 H 0.331439 1.048043 0.713718 0.071 Uiso 1 1 calc R U . . .
C33 C 0.2950(2) 0.8518(11) 0.6464(4) 0.055(2) Uani 1 1 d . . . . .
H33 H 0.277044 0.862682 0.595870 0.066 Uiso 1 1 calc R U . . .
C34 C 0.3301(3) 0.7110(12) 0.6351(4) 0.069(2) Uani 1 1 d . . . . .
H34A H 0.348625 0.771972 0.602617 0.083 Uiso 1 1 calc R U . . .
H34B H 0.317817 0.598244 0.607408 0.083 Uiso 1 1 calc R U . . .
C35 C 0.2869(3) 1.2468(13) 0.5668(5) 0.069(2) Uani 1 1 d . . . . .
C36 C 0.2189(3) 1.3637(14) 0.5963(5) 0.079(3) Uani 1 1 d . . . . .
H36A H 0.201090 1.344080 0.635741 0.119 Uiso 1 1 calc R U . . .
H36B H 0.226754 1.497450 0.595257 0.119 Uiso 1 1 calc R U . . .
H36C H 0.204033 1.327441 0.546333 0.119 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C34 2.114(8) . ?
N1 C1 1.400(8) . ?
N1 C4 1.406(9) . ?
N1 C29 1.470(9) . ?
N2 H2 0.8600 . ?
N2 C9 1.351(8) . ?
N2 C12 1.375(8) . ?
N3 C17 1.402(9) . ?
N3 C20 1.411(10) . ?
N3 C21 1.452(9) . ?
N4 C31 1.463(9) . ?
N4 C35 1.373(10) . ?
N4 C36 1.417(10) . ?
O1 C17 1.199(8) . ?
O2 C20 1.208(9) . ?
O3 C21 1.398(9) . ?
O3 C22 1.415(11) . ?
O4 C29 1.438(8) . ?
O4 C33 1.453(8) . ?
O5 C32 1.441(8) . ?
O5 C35 1.369(11) . ?
O6 C35 1.199(9) . ?
C1 C2 1.393(9) . ?
C1 C9 1.381(9) . ?
C2 C3 1.450(10) . ?
C2 C19 1.401(10) . ?
C3 C4 1.397(10) . ?
C3 C8 1.406(10) . ?
C4 C5 1.385(11) . ?
C5 H5 0.9300 . ?
C5 C6 1.348(13) . ?
C6 H6 0.9300 . ?
C6 C7 1.408(14) . ?
C7 H7 0.9300 . ?
C7 C8 1.384(13) . ?
C8 H8 0.9300 . ?
C9 C10 1.430(9) . ?
C10 C11 1.409(9) . ?
C10 C18 1.353(9) . ?
C11 C12 1.431(9) . ?
C11 C16 1.383(10) . ?
C12 C13 1.396(10) . ?
C13 H13 0.9300 . ?
C13 C14 1.367(10) . ?
C14 H14 0.9300 . ?
C14 C15 1.381(11) . ?
C15 H15 0.9300 . ?
C15 C16 1.397(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.504(9) . ?
C18 C19 1.402(10) . ?
C19 C20 1.509(10) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.514(11) . ?
C23 C24 1.3900 . ?
C23 C28 1.3900 . ?
C24 H24 0.9300 . ?
C24 C25 1.3900 . ?
C25 H25 0.9300 . ?
C25 C26 1.3900 . ?
C26 H26 0.9300 . ?
C26 C27 1.3900 . ?
C27 H27 0.9300 . ?
C27 C28 1.3900 . ?
C28 H28 0.9300 . ?
C29 H29 0.9800 . ?
C29 C30 1.506(10) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C31 1.514(9) . ?
C31 H31 0.9800 . ?
C31 C32 1.544(10) . ?
C32 H32 0.9800 . ?
C32 C33 1.483(10) . ?
C33 H33 0.9800 . ?
C33 C34 1.522(10) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 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
C1 N1 C4 108.6(6) . . ?
C1 N1 C29 123.1(6) . . ?
C4 N1 C29 118.8(6) . . ?
C9 N2 H2 125.3 . . ?
C9 N2 C12 109.3(6) . . ?
C12 N2 H2 125.3 . . ?
C17 N3 C20 112.8(6) . . ?
C17 N3 C21 124.4(7) . . ?
C20 N3 C21 122.0(7) . . ?
C35 N4 C31 110.0(7) . . ?
C35 N4 C36 122.6(7) . . ?
C36 N4 C31 123.8(6) . . ?
C21 O3 C22 113.4(7) . . ?
C29 O4 C33 108.8(5) . . ?
C35 O5 C32 108.1(6) . . ?
C2 C1 N1 108.4(6) . . ?
C9 C1 N1 130.5(6) . . ?
C9 C1 C2 121.1(6) . . ?
C1 C2 C3 107.5(6) . . ?
C1 C2 C19 118.0(7) . . ?
C19 C2 C3 134.5(7) . . ?
C4 C3 C2 107.0(7) . . ?
C4 C3 C8 120.2(8) . . ?
C8 C3 C2 132.8(7) . . ?
C3 C4 N1 108.3(7) . . ?
C5 C4 N1 128.6(7) . . ?
C5 C4 C3 122.9(8) . . ?
C4 C5 H5 122.3 . . ?
C6 C5 C4 115.3(9) . . ?
C6 C5 H5 122.3 . . ?
C5 C6 H6 117.6 . . ?
C5 C6 C7 124.8(10) . . ?
C7 C6 H6 117.6 . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.4(10) . . ?
C8 C7 H7 120.3 . . ?
C3 C8 H8 121.3 . . ?
C7 C8 C3 117.3(9) . . ?
C7 C8 H8 121.3 . . ?
N2 C9 C1 130.5(6) . . ?
N2 C9 C10 109.1(6) . . ?
C1 C9 C10 120.3(7) . . ?
C11 C10 C9 106.6(6) . . ?
C18 C10 C9 118.2(6) . . ?
C18 C10 C11 135.0(6) . . ?
C10 C11 C12 106.5(6) . . ?
C16 C11 C10 135.4(6) . . ?
C16 C11 C12 118.1(6) . . ?
N2 C12 C11 108.4(6) . . ?
N2 C12 C13 130.0(7) . . ?
C13 C12 C11 121.6(7) . . ?
C12 C13 H13 121.1 . . ?
C14 C13 C12 117.8(7) . . ?
C14 C13 H13 121.1 . . ?
C13 C14 H14 119.0 . . ?
C13 C14 C15 122.1(7) . . ?
C15 C14 H14 119.0 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.4(7) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 119.9(7) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
N3 C17 C18 106.5(6) . . ?
O1 C17 N3 123.5(6) . . ?
O1 C17 C18 130.0(7) . . ?
C10 C18 C17 131.5(6) . . ?
C10 C18 C19 121.7(6) . . ?
C19 C18 C17 106.7(6) . . ?
C2 C19 C18 120.5(6) . . ?
C2 C19 C20 129.8(7) . . ?
C18 C19 C20 109.7(6) . . ?
N3 C20 C19 104.3(7) . . ?
O2 C20 N3 125.7(7) . . ?
O2 C20 C19 130.1(8) . . ?
N3 C21 H21A 109.0 . . ?
N3 C21 H21B 109.0 . . ?
O3 C21 N3 113.1(6) . . ?
O3 C21 H21A 109.0 . . ?
O3 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
O3 C22 H22A 109.9 . . ?
O3 C22 H22B 109.9 . . ?
O3 C22 C23 108.7(9) . . ?
H22A C22 H22B 108.3 . . ?
C23 C22 H22A 109.9 . . ?
C23 C22 H22B 109.9 . . ?
C24 C23 C22 120.4(8) . . ?
C24 C23 C28 120.0 . . ?
C28 C23 C22 119.5(8) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 120.0 . . ?
C24 C25 C26 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 120.0 . . ?
C26 C27 C28 120.0 . . ?
C28 C27 H27 120.0 . . ?
C23 C28 H28 120.0 . . ?
C27 C28 C23 120.0 . . ?
C27 C28 H28 120.0 . . ?
N1 C29 H29 107.8 . . ?
N1 C29 C30 113.5(6) . . ?
O4 C29 N1 108.5(6) . . ?
O4 C29 H29 107.8 . . ?
O4 C29 C30 111.1(6) . . ?
C30 C29 H29 107.8 . . ?
C29 C30 H30A 109.1 . . ?
C29 C30 H30B 109.1 . . ?
C29 C30 C31 112.3(6) . . ?
H30A C30 H30B 107.9 . . ?
C31 C30 H30A 109.1 . . ?
C31 C30 H30B 109.1 . . ?
N4 C31 C30 114.3(6) . . ?
N4 C31 H31 109.9 . . ?
N4 C31 C32 98.9(5) . . ?
C30 C31 H31 109.9 . . ?
C30 C31 C32 113.6(6) . . ?
C32 C31 H31 109.9 . . ?
O5 C32 C31 103.5(6) . . ?
O5 C32 H32 110.6 . . ?
O5 C32 C33 107.2(6) . . ?
C31 C32 H32 110.6 . . ?
C33 C32 C31 114.2(6) . . ?
C33 C32 H32 110.6 . . ?
O4 C33 C32 112.0(6) . . ?
O4 C33 H33 106.7 . . ?
O4 C33 C34 107.6(6) . . ?
C32 C33 H33 106.7 . . ?
C32 C33 C34 116.4(7) . . ?
C34 C33 H33 106.7 . . ?
I1 C34 H34A 108.7 . . ?
I1 C34 H34B 108.7 . . ?
C33 C34 I1 114.1(5) . . ?
C33 C34 H34A 108.7 . . ?
C33 C34 H34B 108.7 . . ?
H34A C34 H34B 107.6 . . ?
O5 C35 N4 109.3(7) . . ?
O6 C35 N4 126.9(10) . . ?
O6 C35 O5 123.7(8) . . ?
N4 C36 H36A 109.5 . . ?
N4 C36 H36B 109.5 . . ?
N4 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 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 C1 C2 C3 1.8(8) . . . . ?
N1 C1 C2 C19 -177.8(7) . . . . ?
N1 C1 C9 N2 -6.4(14) . . . . ?
N1 C1 C9 C10 175.8(7) . . . . ?
N1 C4 C5 C6 175.3(10) . . . . ?
N1 C29 C30 C31 177.3(6) . . . . ?
N2 C9 C10 C11 0.5(8) . . . . ?
N2 C9 C10 C18 -175.0(7) . . . . ?
N2 C12 C13 C14 178.9(7) . . . . ?
N3 C17 C18 C10 -177.7(8) . . . . ?
N3 C17 C18 C19 -0.6(8) . . . . ?
N4 C31 C32 O5 30.7(6) . . . . ?
N4 C31 C32 C33 -85.4(7) . . . . ?
O1 C17 C18 C10 2.4(14) . . . . ?
O1 C17 C18 C19 179.5(8) . . . . ?
O3 C22 C23 C24 103.3(10) . . . . ?
O3 C22 C23 C28 -79.5(9) . . . . ?
O4 C29 C30 C31 54.6(8) . . . . ?
O4 C33 C34 I1 -54.3(7) . . . . ?
O5 C32 C33 O4 -161.9(6) . . . . ?
O5 C32 C33 C34 73.7(8) . . . . ?
C1 N1 C4 C3 -3.1(9) . . . . ?
C1 N1 C4 C5 -177.9(10) . . . . ?
C1 N1 C29 O4 79.4(8) . . . . ?
C1 N1 C29 C30 -44.6(10) . . . . ?
C1 C2 C3 C4 -3.7(9) . . . . ?
C1 C2 C3 C8 177.5(9) . . . . ?
C1 C2 C19 C18 1.1(11) . . . . ?
C1 C2 C19 C20 -177.8(7) . . . . ?
C1 C9 C10 C11 178.8(7) . . . . ?
C1 C9 C10 C18 3.2(10) . . . . ?
C2 C1 C9 N2 172.5(8) . . . . ?
C2 C1 C9 C10 -5.2(11) . . . . ?
C2 C3 C4 N1 4.2(9) . . . . ?
C2 C3 C4 C5 179.3(9) . . . . ?
C2 C3 C8 C7 179.4(10) . . . . ?
C2 C19 C20 N3 -178.1(8) . . . . ?
C2 C19 C20 O2 2.6(14) . . . . ?
C3 C2 C19 C18 -178.4(9) . . . . ?
C3 C2 C19 C20 2.8(15) . . . . ?
C3 C4 C5 C6 1.2(16) . . . . ?
C4 N1 C1 C2 0.7(8) . . . . ?
C4 N1 C1 C9 179.8(8) . . . . ?
C4 N1 C29 O4 -138.1(7) . . . . ?
C4 N1 C29 C30 97.8(8) . . . . ?
C4 C3 C8 C7 0.8(15) . . . . ?
C4 C5 C6 C7 0(2) . . . . ?
C5 C6 C7 C8 -1(2) . . . . ?
C6 C7 C8 C3 0.6(19) . . . . ?
C8 C3 C4 N1 -176.9(8) . . . . ?
C8 C3 C4 C5 -1.7(14) . . . . ?
C9 N2 C12 C11 -2.0(8) . . . . ?
C9 N2 C12 C13 178.2(8) . . . . ?
C9 C1 C2 C3 -177.3(7) . . . . ?
C9 C1 C2 C19 3.0(11) . . . . ?
C9 C10 C11 C12 -1.7(8) . . . . ?
C9 C10 C11 C16 180.0(8) . . . . ?
C9 C10 C18 C17 177.7(7) . . . . ?
C9 C10 C18 C19 0.9(10) . . . . ?
C10 C11 C12 N2 2.3(8) . . . . ?
C10 C11 C12 C13 -177.9(7) . . . . ?
C10 C11 C16 C15 179.1(8) . . . . ?
C10 C18 C19 C2 -3.1(11) . . . . ?
C10 C18 C19 C20 175.9(7) . . . . ?
C11 C10 C18 C17 3.7(14) . . . . ?
C11 C10 C18 C19 -173.0(8) . . . . ?
C11 C12 C13 C14 -0.9(11) . . . . ?
C12 N2 C9 C1 -177.0(8) . . . . ?
C12 N2 C9 C10 0.9(8) . . . . ?
C12 C11 C16 C15 0.9(10) . . . . ?
C12 C13 C14 C15 -0.8(12) . . . . ?
C13 C14 C15 C16 2.5(13) . . . . ?
C14 C15 C16 C11 -2.6(12) . . . . ?
C16 C11 C12 N2 -179.0(6) . . . . ?
C16 C11 C12 C13 0.8(11) . . . . ?
C17 N3 C20 O2 176.0(7) . . . . ?
C17 N3 C20 C19 -3.4(8) . . . . ?
C17 N3 C21 O3 99.9(9) . . . . ?
C17 C18 C19 C2 179.4(7) . . . . ?
C17 C18 C19 C20 -1.5(8) . . . . ?
C18 C10 C11 C12 172.7(8) . . . . ?
C18 C10 C11 C16 -5.5(15) . . . . ?
C18 C19 C20 N3 3.0(8) . . . . ?
C18 C19 C20 O2 -176.4(8) . . . . ?
C19 C2 C3 C4 175.8(9) . . . . ?
C19 C2 C3 C8 -3.0(17) . . . . ?
C20 N3 C17 O1 -177.5(7) . . . . ?
C20 N3 C17 C18 2.6(8) . . . . ?
C20 N3 C21 O3 -91.6(9) . . . . ?
C21 N3 C17 O1 -8.0(12) . . . . ?
C21 N3 C17 C18 172.0(7) . . . . ?
C21 N3 C20 O2 6.2(11) . . . . ?
C21 N3 C20 C19 -173.1(7) . . . . ?
C21 O3 C22 C23 162.7(7) . . . . ?
C22 O3 C21 N3 81.3(9) . . . . ?
C22 C23 C24 C25 177.1(9) . . . . ?
C22 C23 C28 C27 -177.2(9) . . . . ?
C23 C24 C25 C26 0.0 . . . . ?
C24 C23 C28 C27 0.0 . . . . ?
C24 C25 C26 C27 0.0 . . . . ?
C25 C26 C27 C28 0.0 . . . . ?
C26 C27 C28 C23 0.0 . . . . ?
C28 C23 C24 C25 0.0 . . . . ?
C29 N1 C1 C2 146.4(7) . . . . ?
C29 N1 C1 C9 -34.5(12) . . . . ?
C29 N1 C4 C3 -150.5(7) . . . . ?
C29 N1 C4 C5 34.7(13) . . . . ?
C29 O4 C33 C32 63.1(8) . . . . ?
C29 O4 C33 C34 -167.6(6) . . . . ?
C29 C30 C31 N4 73.9(8) . . . . ?
C29 C30 C31 C32 -38.6(9) . . . . ?
C30 C31 C32 O5 152.2(6) . . . . ?
C30 C31 C32 C33 36.1(9) . . . . ?
C31 N4 C35 O5 12.0(9) . . . . ?
C31 N4 C35 O6 -167.0(8) . . . . ?
C31 C32 C33 O4 -48.0(8) . . . . ?
C31 C32 C33 C34 -172.4(6) . . . . ?
C32 O5 C35 N4 9.9(9) . . . . ?
C32 O5 C35 O6 -171.1(8) . . . . ?
C32 C33 C34 I1 72.4(7) . . . . ?
C33 O4 C29 N1 168.1(5) . . . . ?
C33 O4 C29 C30 -66.5(7) . . . . ?
C35 N4 C31 C30 -147.4(7) . . . . ?
C35 N4 C31 C32 -26.4(7) . . . . ?
C35 O5 C32 C31 -26.1(8) . . . . ?
C35 O5 C32 C33 94.9(8) . . . . ?
C36 N4 C31 C30 53.7(9) . . . . ?
C36 N4 C31 C32 174.7(7) . . . . ?
C36 N4 C35 O5 171.1(7) . . . . ?
C36 N4 C35 O6 -7.8(13) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.234 0.500 494.3 23.5 ?
2 0.500 -0.462 0.500 494.3 23.5 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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_090326c
_database_code_depnum_ccdc_archive 'CCDC 2168508'
loop_
_audit_author_name
_audit_author_address
'Liping Wang'
;Guizhou Medcial University
China
;
_audit_update_record             
;
2022-04-25 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;
_audit_creation_date             2022-03-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C36 H27 I N4 O6, C H2 Cl2'
_chemical_formula_sum            'C37 H29 Cl2 I N4 O6'
_chemical_formula_weight         823.44
_chemical_absolute_configuration ad
_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'
I I -0.4742 1.8119 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.5952(12)
_cell_length_b                   16.734(2)
_cell_length_c                   12.2057(16)
_cell_angle_alpha                90
_cell_angle_beta                 107.210(2)
_cell_angle_gamma                90
_cell_volume                     1677.0(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4089
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.671
_cell_measurement_theta_min      2.434
_shelx_estimated_absorpt_T_max   0.892
_shelx_estimated_absorpt_T_min   0.652
_exptl_absorpt_coefficient_mu    1.169
_exptl_absorpt_correction_T_max  0.8441
_exptl_absorpt_correction_T_min  0.6520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             828
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8591
_diffrn_reflns_point_group_measured_fraction_full 0.845
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        25.020
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         1.747
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.634
_reflns_Friedel_fraction_full    0.682
_reflns_Friedel_fraction_max     0.682
_reflns_number_gt                4184
_reflns_number_total             5002
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 1421 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         5002
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.092
_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)+(0.0166P)²+0.9026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0648
_refine_ls_wR_factor_ref         0.0719
_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:
 C21(H21), C23(H23), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C37(H37A,H37B)
2.c Me refined with riding coordinates:
 C27(H27A,H27B,H27C)
2.d Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C15(H15), C16(H16),
 C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
;
_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
I1 I 0.55681(5) 0.34508(3) 0.38237(4) 0.05585(15) Uani 1 1 d . . . . .
Cl1 Cl 0.4720(3) 0.96066(16) 0.1505(2) 0.0828(7) Uani 1 1 d . . . . .
Cl2 Cl 0.6070(3) 0.82372(12) 0.2927(2) 0.0885(8) Uani 1 1 d . . . . .
N1 N 0.4149(6) 0.6046(3) 0.4534(4) 0.0318(12) Uani 1 1 d . . . . .
N2 N 0.7444(6) 0.5167(3) 0.4615(4) 0.0279(11) Uani 1 1 d . . . . .
N3 N 0.5010(6) 0.6683(3) 0.0036(4) 0.0371(13) Uani 1 1 d . . . . .
N4 N 0.9291(7) 0.6230(4) 0.7405(5) 0.0547(16) Uani 1 1 d . . . . .
O1 O 0.2678(5) 0.7226(3) 0.0293(4) 0.0481(12) Uani 1 1 d . . . . .
O2 O 0.7439(6) 0.6017(3) 0.0316(4) 0.0505(12) Uani 1 1 d . . . . .
O3 O 0.5397(5) 0.4956(2) 0.5563(3) 0.0339(10) Uani 1 1 d . . . . .
O4 O 0.5923(6) 0.7563(3) -0.1171(4) 0.0443(11) Uani 1 1 d . . . . .
O5 O 0.9789(5) 0.5032(3) 0.6861(4) 0.0440(12) Uani 1 1 d . . . . .
O6 O 1.1865(6) 0.5902(3) 0.7348(5) 0.0609(15) Uani 1 1 d . . . . .
C1 C 0.4898(7) 0.5987(4) 0.3702(5) 0.0274(14) Uani 1 1 d . . . . .
C2 C 0.3967(7) 0.6411(3) 0.2710(5) 0.0286(13) Uani 1 1 d . . . . .
C3 C 0.2548(8) 0.6705(4) 0.2999(5) 0.0309(15) Uani 1 1 d . . . . .
C4 C 0.2710(7) 0.6489(4) 0.4131(5) 0.0341(15) Uani 1 1 d . . . . .
C5 C 0.1558(8) 0.6681(4) 0.4681(6) 0.0381(16) Uani 1 1 d . . . . .
H5 H 0.168735 0.653152 0.543692 0.046 Uiso 1 1 calc R U . . .
C6 C 0.0216(8) 0.7102(4) 0.4054(7) 0.0455(17) Uani 1 1 d . . . . .
H6 H -0.058397 0.724083 0.439195 0.055 Uiso 1 1 calc R U . . .
C7 C 0.0029(8) 0.7325(4) 0.2925(7) 0.0464(18) Uani 1 1 d . . . . .
H7 H -0.089413 0.760961 0.252493 0.056 Uiso 1 1 calc R U . . .
C8 C 0.1178(8) 0.7136(4) 0.2385(6) 0.0401(17) Uani 1 1 d . . . . .
H8 H 0.104476 0.729142 0.163068 0.048 Uiso 1 1 calc R U . . .
C9 C 0.6360(7) 0.5608(3) 0.3726(5) 0.0280(13) Uani 1 1 d . . . . .
C10 C 0.6965(7) 0.5656(3) 0.2779(5) 0.0293(14) Uani 1 1 d . . . . .
C11 C 0.8480(7) 0.5216(3) 0.3072(5) 0.0317(14) Uani 1 1 d . . . . .
C12 C 0.8727(7) 0.4915(3) 0.4179(5) 0.0324(14) Uani 1 1 d . . . . .
C13 C 1.0098(8) 0.4449(4) 0.4696(6) 0.0371(16) Uani 1 1 d . . . . .
H13 H 1.028240 0.425070 0.543490 0.044 Uiso 1 1 calc R U . . .
C14 C 1.1170(8) 0.4293(4) 0.4072(6) 0.0479(18) Uani 1 1 d . . . . .
H14 H 1.207511 0.397441 0.439905 0.057 Uiso 1 1 calc R U . . .
C15 C 1.0947(9) 0.4592(4) 0.2981(7) 0.051(2) Uani 1 1 d . . . . .
H15 H 1.169638 0.448092 0.258659 0.062 Uiso 1 1 calc R U . . .
C16 C 0.9598(8) 0.5059(4) 0.2484(6) 0.0431(17) Uani 1 1 d . . . . .
H16 H 0.943984 0.526798 0.175332 0.052 Uiso 1 1 calc R U . . .
C17 C 0.3906(8) 0.6839(4) 0.0649(5) 0.0338(14) Uani 1 1 d . . . . .
C18 C 0.4570(7) 0.6441(3) 0.1783(5) 0.0279(13) Uani 1 1 d . . . . .
C19 C 0.6050(7) 0.6081(4) 0.1803(5) 0.0306(14) Uani 1 1 d . . . . .
C20 C 0.6336(8) 0.6230(4) 0.0681(5) 0.0362(15) Uani 1 1 d . . . . .
C21 C 0.4978(8) 0.5768(4) 0.5690(5) 0.0335(16) Uani 1 1 d . . . . .
H21 H 0.421605 0.578599 0.614864 0.040 Uiso 1 1 calc R U . . .
C22 C 0.6423(8) 0.6297(4) 0.6245(5) 0.0371(15) Uani 1 1 d . . . . .
H22A H 0.605843 0.675596 0.658727 0.045 Uiso 1 1 calc R U . . .
H22B H 0.688961 0.649003 0.566210 0.045 Uiso 1 1 calc R U . . .
C23 C 0.7727(7) 0.5853(4) 0.7165(5) 0.0402(16) Uani 1 1 d . . . . .
H23 H 0.740468 0.581440 0.786936 0.048 Uiso 1 1 calc R U . . .
C24 C 0.8086(8) 0.5018(4) 0.6784(6) 0.0364(16) Uani 1 1 d . . . . .
H24 H 0.792471 0.462706 0.733833 0.044 Uiso 1 1 calc R U . . .
C25 C 0.7019(7) 0.4767(3) 0.5570(5) 0.0321(14) Uani 1 1 d . . . . .
C26 C 1.0453(9) 0.5763(4) 0.7232(5) 0.0423(17) Uani 1 1 d . . . . .
C27 C 0.9607(12) 0.7050(6) 0.7826(11) 0.106(4) Uani 1 1 d . . . . .
H27A H 0.861752 0.728295 0.789248 0.158 Uiso 1 1 calc R U . . .
H27B H 1.041193 0.704788 0.856439 0.158 Uiso 1 1 calc R U . . .
H27C H 0.999787 0.735819 0.729869 0.158 Uiso 1 1 calc R U . . .
C28 C 0.7021(8) 0.3862(4) 0.5463(5) 0.0393(16) Uani 1 1 d . . . . .
H28A H 0.661242 0.362994 0.605237 0.047 Uiso 1 1 calc R U . . .
H28B H 0.813138 0.367909 0.559364 0.047 Uiso 1 1 calc R U . . .
C29 C 0.4825(8) 0.6957(4) -0.1118(5) 0.0419(16) Uani 1 1 d . . . . .
H29A H 0.497937 0.650864 -0.157808 0.050 Uiso 1 1 calc R U . . .
H29B H 0.372365 0.715336 -0.144807 0.050 Uiso 1 1 calc R U . . .
C30 C 0.5670(9) 0.8285(4) -0.0627(6) 0.052(2) Uani 1 1 d . . . . .
H30A H 0.539996 0.816408 0.007235 0.062 Uiso 1 1 calc R U . . .
H30B H 0.477499 0.858383 -0.113200 0.062 Uiso 1 1 calc R U . . .
C31 C 0.7222(9) 0.8773(4) -0.0354(6) 0.0441(17) Uani 1 1 d . . . . .
C32 C 0.8718(8) 0.8425(6) 0.0045(5) 0.0566(17) Uani 1 1 d . . . . .
H32 H 0.878760 0.787205 0.011634 0.068 Uiso 1 1 calc R U . . .
C33 C 1.0121(10) 0.8867(4) 0.0344(7) 0.060(2) Uani 1 1 d . . . . .
H33 H 1.112428 0.861300 0.061263 0.072 Uiso 1 1 calc R U . . .
C34 C 1.0054(10) 0.9675(5) 0.0248(6) 0.055(2) Uani 1 1 d . . . . .
H34 H 1.100626 0.997637 0.043884 0.066 Uiso 1 1 calc R U . . .
C35 C 0.8558(11) 1.0044(5) -0.0134(7) 0.062(2) Uani 1 1 d . . . . .
H35 H 0.849226 1.059858 -0.017229 0.075 Uiso 1 1 calc R U . . .
C36 C 0.7168(10) 0.9593(4) -0.0457(7) 0.059(2) Uani 1 1 d . . . . .
H36 H 0.616683 0.984558 -0.075170 0.071 Uiso 1 1 calc R U . . .
C37 C 0.6445(9) 0.9190(5) 0.2475(8) 0.068(2) Uani 1 1 d . . . . .
H37A H 0.681277 0.953702 0.313812 0.082 Uiso 1 1 calc R U . . .
H37B H 0.731124 0.915678 0.211658 0.082 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C28 2.135(6) . ?
Cl1 C37 1.746(8) . ?
Cl2 C37 1.748(9) . ?
N1 C1 1.357(8) . ?
N1 C4 1.400(8) . ?
N1 C21 1.457(7) . ?
N2 C9 1.410(7) . ?
N2 C12 1.424(7) . ?
N2 C25 1.480(7) . ?
N3 C17 1.396(8) . ?
N3 C20 1.401(8) . ?
N3 C29 1.445(8) . ?
N4 C23 1.434(9) . ?
N4 C26 1.334(9) . ?
N4 C27 1.463(10) . ?
O1 C17 1.204(7) . ?
O2 C20 1.214(7) . ?
O3 C21 1.426(7) . ?
O3 C25 1.427(7) . ?
O4 C29 1.399(7) . ?
O4 C30 1.426(8) . ?
O5 C24 1.439(8) . ?
O5 C26 1.369(8) . ?
O6 C26 1.202(8) . ?
C1 C2 1.427(8) . ?
C1 C9 1.401(8) . ?
C2 C3 1.453(9) . ?
C2 C18 1.378(8) . ?
C3 C4 1.394(9) . ?
C3 C8 1.395(8) . ?
C4 C5 1.389(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.375(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.390(10) . ?
C7 H7 0.9300 . ?
C7 C8 1.377(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.403(8) . ?
C10 C11 1.446(8) . ?
C10 C19 1.410(8) . ?
C11 C12 1.398(8) . ?
C11 C16 1.383(9) . ?
C12 C13 1.398(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(10) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.489(8) . ?
C18 C19 1.401(8) . ?
C19 C20 1.482(9) . ?
C21 H21 0.9800 . ?
C21 C22 1.512(9) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.524(8) . ?
C23 H23 0.9800 . ?
C23 C24 1.534(9) . ?
C24 H24 0.9800 . ?
C24 C25 1.551(9) . ?
C25 C28 1.520(8) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C31 1.515(9) . ?
C31 C32 1.364(9) . ?
C31 C36 1.377(9) . ?
C32 H32 0.9300 . ?
C32 C33 1.369(10) . ?
C33 H33 0.9300 . ?
C33 C34 1.357(10) . ?
C34 H34 0.9300 . ?
C34 C35 1.377(11) . ?
C35 H35 0.9300 . ?
C35 C36 1.369(11) . ?
C36 H36 0.9300 . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?

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
C1 N1 C4 109.9(5) . . ?
C1 N1 C21 119.8(6) . . ?
C4 N1 C21 129.6(6) . . ?
C9 N2 C12 106.0(5) . . ?
C9 N2 C25 125.6(5) . . ?
C12 N2 C25 124.0(4) . . ?
C17 N3 C20 111.6(5) . . ?
C17 N3 C29 124.6(5) . . ?
C20 N3 C29 123.8(6) . . ?
C23 N4 C27 123.4(7) . . ?
C26 N4 C23 114.2(6) . . ?
C26 N4 C27 122.4(7) . . ?
C21 O3 C25 119.2(5) . . ?
C29 O4 C30 113.2(5) . . ?
C26 O5 C24 110.7(5) . . ?
N1 C1 C2 109.2(5) . . ?
N1 C1 C9 129.7(6) . . ?
C9 C1 C2 121.1(6) . . ?
C1 C2 C3 105.2(5) . . ?
C18 C2 C1 117.6(5) . . ?
C18 C2 C3 137.2(5) . . ?
C4 C3 C2 107.9(5) . . ?
C4 C3 C8 119.2(6) . . ?
C8 C3 C2 132.9(6) . . ?
C3 C4 N1 107.7(5) . . ?
C5 C4 N1 129.4(6) . . ?
C5 C4 C3 122.9(6) . . ?
C4 C5 H5 121.6 . . ?
C6 C5 C4 116.7(7) . . ?
C6 C5 H5 121.6 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.4(7) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.6(7) . . ?
C8 C7 H7 119.2 . . ?
C3 C8 H8 120.9 . . ?
C7 C8 C3 118.2(7) . . ?
C7 C8 H8 120.9 . . ?
C1 C9 N2 129.5(6) . . ?
C1 C9 C10 120.4(5) . . ?
C10 C9 N2 110.1(5) . . ?
C9 C10 C11 107.1(5) . . ?
C9 C10 C19 118.4(5) . . ?
C19 C10 C11 134.6(6) . . ?
C12 C11 C10 106.9(5) . . ?
C16 C11 C10 133.0(6) . . ?
C16 C11 C12 120.1(5) . . ?
C11 C12 N2 110.0(5) . . ?
C13 C12 N2 129.8(6) . . ?
C13 C12 C11 120.3(6) . . ?
C12 C13 H13 121.1 . . ?
C14 C13 C12 117.8(6) . . ?
C14 C13 H13 121.1 . . ?
C13 C14 H14 118.8 . . ?
C15 C14 C13 122.5(6) . . ?
C15 C14 H14 118.8 . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.2(7) . . ?
C16 C15 H15 120.4 . . ?
C11 C16 H16 119.9 . . ?
C15 C16 C11 120.1(6) . . ?
C15 C16 H16 119.9 . . ?
N3 C17 C18 106.3(5) . . ?
O1 C17 N3 124.7(6) . . ?
O1 C17 C18 129.1(6) . . ?
C2 C18 C17 130.2(6) . . ?
C2 C18 C19 122.0(5) . . ?
C19 C18 C17 107.8(5) . . ?
C10 C19 C20 131.5(6) . . ?
C18 C19 C10 120.6(6) . . ?
C18 C19 C20 108.0(5) . . ?
N3 C20 C19 106.3(5) . . ?
O2 C20 N3 123.1(6) . . ?
O2 C20 C19 130.6(6) . . ?
N1 C21 H21 109.0 . . ?
N1 C21 C22 110.4(5) . . ?
O3 C21 N1 105.5(5) . . ?
O3 C21 H21 109.0 . . ?
O3 C21 C22 114.0(5) . . ?
C22 C21 H21 109.0 . . ?
C21 C22 H22A 109.2 . . ?
C21 C22 H22B 109.2 . . ?
C21 C22 C23 111.9(5) . . ?
H22A C22 H22B 107.9 . . ?
C23 C22 H22A 109.2 . . ?
C23 C22 H22B 109.2 . . ?
N4 C23 C22 112.1(6) . . ?
N4 C23 H23 109.9 . . ?
N4 C23 C24 101.7(5) . . ?
C22 C23 H23 109.9 . . ?
C22 C23 C24 113.0(5) . . ?
C24 C23 H23 109.9 . . ?
O5 C24 C23 104.9(5) . . ?
O5 C24 H24 108.4 . . ?
O5 C24 C25 111.7(5) . . ?
C23 C24 H24 108.4 . . ?
C23 C24 C25 114.9(5) . . ?
C25 C24 H24 108.4 . . ?
N2 C25 C24 114.6(5) . . ?
N2 C25 C28 112.1(5) . . ?
O3 C25 N2 111.3(4) . . ?
O3 C25 C24 104.3(5) . . ?
O3 C25 C28 104.2(5) . . ?
C28 C25 C24 109.6(5) . . ?
N4 C26 O5 108.5(6) . . ?
O6 C26 N4 130.1(7) . . ?
O6 C26 O5 121.4(7) . . ?
N4 C27 H27A 109.5 . . ?
N4 C27 H27B 109.5 . . ?
N4 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
I1 C28 H28A 109.0 . . ?
I1 C28 H28B 109.0 . . ?
C25 C28 I1 112.7(4) . . ?
C25 C28 H28A 109.0 . . ?
C25 C28 H28B 109.0 . . ?
H28A C28 H28B 107.8 . . ?
N3 C29 H29A 108.9 . . ?
N3 C29 H29B 108.9 . . ?
O4 C29 N3 113.2(5) . . ?
O4 C29 H29A 108.9 . . ?
O4 C29 H29B 108.9 . . ?
H29A C29 H29B 107.7 . . ?
O4 C30 H30A 110.0 . . ?
O4 C30 H30B 110.0 . . ?
O4 C30 C31 108.3(6) . . ?
H30A C30 H30B 108.4 . . ?
C31 C30 H30A 110.0 . . ?
C31 C30 H30B 110.0 . . ?
C32 C31 C30 121.6(7) . . ?
C32 C31 C36 117.5(8) . . ?
C36 C31 C30 120.9(7) . . ?
C31 C32 H32 119.1 . . ?
C31 C32 C33 121.8(9) . . ?
C33 C32 H32 119.1 . . ?
C32 C33 H33 119.9 . . ?
C34 C33 C32 120.3(8) . . ?
C34 C33 H33 119.9 . . ?
C33 C34 H34 120.4 . . ?
C33 C34 C35 119.2(8) . . ?
C35 C34 H34 120.4 . . ?
C34 C35 H35 120.0 . . ?
C36 C35 C34 119.9(7) . . ?
C36 C35 H35 120.0 . . ?
C31 C36 H36 119.3 . . ?
C35 C36 C31 121.3(8) . . ?
C35 C36 H36 119.3 . . ?
Cl1 C37 Cl2 112.3(5) . . ?
Cl1 C37 H37A 109.1 . . ?
Cl1 C37 H37B 109.1 . . ?
Cl2 C37 H37A 109.1 . . ?
Cl2 C37 H37B 109.1 . . ?
H37A C37 H37B 107.9 . . ?

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 C1 C2 C3 -2.3(7) . . . . ?
N1 C1 C2 C18 177.8(5) . . . . ?
N1 C1 C9 N2 1.5(11) . . . . ?
N1 C1 C9 C10 -176.5(6) . . . . ?
N1 C4 C5 C6 -177.5(6) . . . . ?
N1 C21 C22 C23 -154.1(5) . . . . ?
N2 C9 C10 C11 1.0(6) . . . . ?
N2 C9 C10 C19 -179.5(5) . . . . ?
N2 C12 C13 C14 -179.8(6) . . . . ?
N2 C25 C28 I1 -52.0(6) . . . . ?
N3 C17 C18 C2 179.6(6) . . . . ?
N3 C17 C18 C19 1.2(6) . . . . ?
N4 C23 C24 O5 0.2(6) . . . . ?
N4 C23 C24 C25 -122.8(6) . . . . ?
O1 C17 C18 C2 -0.1(11) . . . . ?
O1 C17 C18 C19 -178.6(6) . . . . ?
O3 C21 C22 C23 -35.6(8) . . . . ?
O3 C25 C28 I1 68.5(5) . . . . ?
O4 C30 C31 C32 -40.2(9) . . . . ?
O4 C30 C31 C36 142.5(7) . . . . ?
O5 C24 C25 N2 -45.4(7) . . . . ?
O5 C24 C25 O3 -167.4(5) . . . . ?
O5 C24 C25 C28 81.6(6) . . . . ?
C1 N1 C4 C3 0.7(7) . . . . ?
C1 N1 C4 C5 178.5(6) . . . . ?
C1 N1 C21 O3 -55.4(8) . . . . ?
C1 N1 C21 C22 68.1(7) . . . . ?
C1 C2 C3 C4 2.7(7) . . . . ?
C1 C2 C3 C8 -177.8(7) . . . . ?
C1 C2 C18 C17 -179.0(6) . . . . ?
C1 C2 C18 C19 -0.8(8) . . . . ?
C1 C9 C10 C11 179.4(5) . . . . ?
C1 C9 C10 C19 -1.2(8) . . . . ?
C2 C1 C9 N2 179.7(5) . . . . ?
C2 C1 C9 C10 1.8(9) . . . . ?
C2 C3 C4 N1 -2.2(7) . . . . ?
C2 C3 C4 C5 179.9(6) . . . . ?
C2 C3 C8 C7 -179.9(7) . . . . ?
C2 C18 C19 C10 1.4(9) . . . . ?
C2 C18 C19 C20 -179.6(5) . . . . ?
C3 C2 C18 C17 1.1(12) . . . . ?
C3 C2 C18 C19 179.4(6) . . . . ?
C3 C4 C5 C6 0.0(10) . . . . ?
C4 N1 C1 C2 1.0(7) . . . . ?
C4 N1 C1 C9 179.5(6) . . . . ?
C4 N1 C21 O3 134.6(6) . . . . ?
C4 N1 C21 C22 -101.9(8) . . . . ?
C4 C3 C8 C7 -0.5(9) . . . . ?
C4 C5 C6 C7 -0.1(10) . . . . ?
C5 C6 C7 C8 -0.1(11) . . . . ?
C6 C7 C8 C3 0.4(11) . . . . ?
C8 C3 C4 N1 178.3(6) . . . . ?
C8 C3 C4 C5 0.4(9) . . . . ?
C9 N2 C12 C11 2.3(6) . . . . ?
C9 N2 C12 C13 -178.6(6) . . . . ?
C9 N2 C25 O3 -6.7(8) . . . . ?
C9 N2 C25 C24 -124.7(6) . . . . ?
C9 N2 C25 C28 109.6(6) . . . . ?
C9 C1 C2 C3 179.1(5) . . . . ?
C9 C1 C2 C18 -0.8(8) . . . . ?
C9 C10 C11 C12 0.4(7) . . . . ?
C9 C10 C11 C16 179.9(7) . . . . ?
C9 C10 C19 C18 -0.4(8) . . . . ?
C9 C10 C19 C20 -179.1(6) . . . . ?
C10 C11 C12 N2 -1.7(7) . . . . ?
C10 C11 C12 C13 179.1(5) . . . . ?
C10 C11 C16 C15 -178.2(7) . . . . ?
C10 C19 C20 N3 179.3(6) . . . . ?
C10 C19 C20 O2 0.5(12) . . . . ?
C11 C10 C19 C18 178.9(6) . . . . ?
C11 C10 C19 C20 0.2(12) . . . . ?
C11 C12 C13 C14 -0.8(9) . . . . ?
C12 N2 C9 C1 179.8(6) . . . . ?
C12 N2 C9 C10 -2.0(6) . . . . ?
C12 N2 C25 O3 -159.6(5) . . . . ?
C12 N2 C25 C24 82.4(7) . . . . ?
C12 N2 C25 C28 -43.4(7) . . . . ?
C12 C11 C16 C15 1.1(10) . . . . ?
C12 C13 C14 C15 1.3(11) . . . . ?
C13 C14 C15 C16 -0.7(12) . . . . ?
C14 C15 C16 C11 -0.6(11) . . . . ?
C16 C11 C12 N2 178.8(6) . . . . ?
C16 C11 C12 C13 -0.4(9) . . . . ?
C17 N3 C20 O2 179.2(6) . . . . ?
C17 N3 C20 C19 0.3(7) . . . . ?
C17 N3 C29 O4 108.5(7) . . . . ?
C17 C18 C19 C10 180.0(5) . . . . ?
C17 C18 C19 C20 -1.0(6) . . . . ?
C18 C2 C3 C4 -177.4(7) . . . . ?
C18 C2 C3 C8 2.0(12) . . . . ?
C18 C19 C20 N3 0.5(6) . . . . ?
C18 C19 C20 O2 -178.4(7) . . . . ?
C19 C10 C11 C12 -178.9(6) . . . . ?
C19 C10 C11 C16 0.5(12) . . . . ?
C20 N3 C17 O1 178.9(6) . . . . ?
C20 N3 C17 C18 -0.9(7) . . . . ?
C20 N3 C29 O4 -71.0(8) . . . . ?
C21 N1 C1 C2 -170.8(5) . . . . ?
C21 N1 C1 C9 7.6(10) . . . . ?
C21 N1 C4 C3 171.5(6) . . . . ?
C21 N1 C4 C5 -10.7(11) . . . . ?
C21 O3 C25 N2 -61.1(6) . . . . ?
C21 O3 C25 C24 63.0(6) . . . . ?
C21 O3 C25 C28 177.9(5) . . . . ?
C21 C22 C23 N4 159.3(6) . . . . ?
C21 C22 C23 C24 45.2(8) . . . . ?
C22 C23 C24 O5 120.5(6) . . . . ?
C22 C23 C24 C25 -2.5(8) . . . . ?
C23 N4 C26 O5 0.0(8) . . . . ?
C23 N4 C26 O6 179.6(7) . . . . ?
C23 C24 C25 N2 73.8(7) . . . . ?
C23 C24 C25 O3 -48.1(7) . . . . ?
C23 C24 C25 C28 -159.1(6) . . . . ?
C24 O5 C26 N4 0.1(7) . . . . ?
C24 O5 C26 O6 -179.5(6) . . . . ?
C24 C25 C28 I1 179.5(4) . . . . ?
C25 N2 C9 C1 22.9(9) . . . . ?
C25 N2 C9 C10 -158.9(5) . . . . ?
C25 N2 C12 C11 159.7(5) . . . . ?
C25 N2 C12 C13 -21.2(10) . . . . ?
C25 O3 C21 N1 99.8(6) . . . . ?
C25 O3 C21 C22 -21.4(7) . . . . ?
C26 N4 C23 C22 -121.1(6) . . . . ?
C26 N4 C23 C24 -0.1(7) . . . . ?
C26 O5 C24 C23 -0.2(7) . . . . ?
C26 O5 C24 C25 124.9(5) . . . . ?
C27 N4 C23 C22 60.1(10) . . . . ?
C27 N4 C23 C24 -178.9(8) . . . . ?
C27 N4 C26 O5 178.8(8) . . . . ?
C27 N4 C26 O6 -1.6(13) . . . . ?
C29 N3 C17 O1 -0.7(10) . . . . ?
C29 N3 C17 C18 179.6(5) . . . . ?
C29 N3 C20 O2 -1.2(10) . . . . ?
C29 N3 C20 C19 179.8(5) . . . . ?
C29 O4 C30 C31 159.7(5) . . . . ?
C30 O4 C29 N3 -65.3(7) . . . . ?
C30 C31 C32 C33 -176.9(7) . . . . ?
C30 C31 C36 C35 175.3(7) . . . . ?
C31 C32 C33 C34 0.0(12) . . . . ?
C32 C31 C36 C35 -2.2(11) . . . . ?
C32 C33 C34 C35 1.0(12) . . . . ?
C33 C34 C35 C36 -2.7(12) . . . . ?
C34 C35 C36 C31 3.4(13) . . . . ?
C36 C31 C32 C33 0.5(11) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.190 0.845 0.821 15.4 0.0 ?
2 0.810 0.345 0.179 15.4 0.0 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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_101210a
_database_code_depnum_ccdc_archive 'CCDC 2168510'
loop_
_audit_author_name
_audit_author_address
'Liping Wang'
;Guizhou Medcial University
China
;

_audit_update_record             
;
2022-04-25 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;
# ----------------------------------------------------------------------------

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H26 N4 O5'
_chemical_formula_weight         510.54

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.8448(6)
_cell_length_b                   12.8096(11)
_cell_length_c                   23.957(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2407.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1736
_cell_measurement_theta_min      3.006
_cell_measurement_theta_max      26.181

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9693
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_process_details   sadabs

_exptl_special_details           ?

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12286
_diffrn_reflns_av_R_equivalents  0.1119
_diffrn_reflns_av_sigmaI/netI    0.0772
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2441
_reflns_number_gt                1481
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0464P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(10)
_refine_ls_number_reflns         2441
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1093
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4567(7) 0.5587(3) 0.64429(18) 0.0678(12) Uani 1 1 d . . .
N2 N 0.4861(5) 0.2492(3) 0.68878(15) 0.0533(10) Uani 1 1 d . . .
N3 N 0.8445(6) 0.2660(3) 0.62830(17) 0.0595(11) Uani 1 1 d . . .
N4 N 0.5330(7) -0.1090(3) 0.53508(19) 0.0783(14) Uani 1 1 d . . .
H4 H 0.5083 -0.1629 0.5153 0.094 Uiso 1 1 calc R . .
O1 O 0.3294(5) 0.4440(3) 0.69968(17) 0.0808(12) Uani 1 1 d . . .
O2 O 0.1656(7) 0.5405(3) 0.6428(2) 0.1034(15) Uani 1 1 d . . .
O3 O 0.7518(5) 0.3287(2) 0.71308(13) 0.0610(9) Uani 1 1 d . . .
O4 O 0.2868(6) -0.1074(3) 0.58669(16) 0.0815(12) Uani 1 1 d . . .
O5 O 1.0253(6) 0.7735(4) 0.5489(2) 0.1196(17) Uani 1 1 d . . .
H5 H 1.0973 0.8188 0.5543 0.179 Uiso 1 1 calc R . .
C1 C 0.3071(11) 0.5186(5) 0.6595(3) 0.0800(18) Uani 1 1 d . . .
C2 C 0.5728(7) 0.3284(4) 0.72416(19) 0.0570(13) Uani 1 1 d . . .
C3 C 0.5083(8) 0.4422(4) 0.7143(2) 0.0684(16) Uani 1 1 d . . .
H3 H 0.5216 0.4805 0.7495 0.082 Uiso 1 1 calc R . .
C4 C 0.5987(7) 0.5041(4) 0.6690(2) 0.0632(15) Uani 1 1 d . . .
H4A H 0.6799 0.5534 0.6854 0.076 Uiso 1 1 calc R . .
C5 C 0.6875(7) 0.4315(4) 0.6288(2) 0.0668(15) Uani 1 1 d . . .
H5A H 0.7484 0.4722 0.6010 0.080 Uiso 1 1 calc R . .
H5B H 0.6036 0.3890 0.6096 0.080 Uiso 1 1 calc R . .
C6 C 0.8134(7) 0.3605(4) 0.6599(2) 0.0609(14) Uani 1 1 d . . .
H6 H 0.9214 0.3978 0.6649 0.073 Uiso 1 1 calc R . .
C7 C 0.3292(7) 0.2016(4) 0.7028(2) 0.0561(13) Uani 1 1 d . . .
C8 C 0.2014(7) 0.2374(4) 0.7389(2) 0.0644(14) Uani 1 1 d . . .
H8 H 0.2104 0.3013 0.7571 0.077 Uiso 1 1 calc R . .
C9 C 0.0599(8) 0.1728(5) 0.7463(2) 0.0784(17) Uani 1 1 d . . .
H9 H -0.0244 0.1926 0.7715 0.094 Uiso 1 1 calc R . .
C10 C 0.0411(8) 0.0796(5) 0.7171(2) 0.0761(16) Uani 1 1 d . . .
H10 H -0.0558 0.0389 0.7224 0.091 Uiso 1 1 calc R . .
C11 C 0.1635(7) 0.0478(4) 0.6809(2) 0.0656(14) Uani 1 1 d . . .
H11 H 0.1496 -0.0141 0.6612 0.079 Uiso 1 1 calc R . .
C12 C 0.3099(7) 0.1075(4) 0.6732(2) 0.0544(13) Uani 1 1 d . . .
C13 C 0.4614(7) 0.0934(4) 0.64026(19) 0.0538(13) Uani 1 1 d . . .
C14 C 0.5663(6) 0.1810(4) 0.65159(19) 0.0525(12) Uani 1 1 d . . .
C15 C 0.7239(6) 0.1886(4) 0.6240(2) 0.0517(12) Uani 1 1 d . . .
C16 C 0.7809(7) 0.1137(4) 0.5855(2) 0.0547(13) Uani 1 1 d . . .
C17 C 0.9480(7) 0.1453(4) 0.56723(19) 0.0583(14) Uani 1 1 d . . .
C18 C 1.0689(7) 0.1024(4) 0.5302(2) 0.0656(15) Uani 1 1 d . . .
H18 H 1.0478 0.0395 0.5122 0.079 Uiso 1 1 calc R . .
C19 C 1.2182(8) 0.1556(6) 0.5214(2) 0.0835(19) Uani 1 1 d . . .
H19 H 1.3005 0.1278 0.4978 0.100 Uiso 1 1 calc R . .
C20 C 1.2475(8) 0.2504(6) 0.5475(2) 0.0813(18) Uani 1 1 d . . .
H20 H 1.3496 0.2848 0.5404 0.098 Uiso 1 1 calc R . .
C21 C 1.1325(7) 0.2963(5) 0.5836(2) 0.0766(17) Uani 1 1 d . . .
H21 H 1.1540 0.3603 0.6004 0.092 Uiso 1 1 calc R . .
C22 C 0.9817(7) 0.2409(4) 0.5933(2) 0.0609(14) Uani 1 1 d . . .
C23 C 0.4298(9) -0.0706(4) 0.5747(2) 0.0641(15) Uani 1 1 d . . .
C24 C 0.5154(7) 0.0202(3) 0.5994(2) 0.0544(13) Uani 1 1 d . . .
C25 C 0.6717(7) 0.0303(4) 0.57318(19) 0.0574(13) Uani 1 1 d . . .
C26 C 0.6889(8) -0.0512(4) 0.5290(2) 0.0746(16) Uani 1 1 d . . .
H26A H 0.6976 -0.0201 0.4922 0.090 Uiso 1 1 calc R . .
H26B H 0.7875 -0.0952 0.5355 0.090 Uiso 1 1 calc R . .
C27 C 0.4737(8) 0.6324(4) 0.5989(2) 0.0874(19) Uani 1 1 d . . .
H27A H 0.4990 0.5955 0.5650 0.131 Uiso 1 1 calc R . .
H27B H 0.5644 0.6804 0.6070 0.131 Uiso 1 1 calc R . .
H27C H 0.3690 0.6703 0.5945 0.131 Uiso 1 1 calc R . .
C28 C 0.5664(8) 0.2978(4) 0.78537(19) 0.0719(16) Uani 1 1 d . . .
H28A H 0.6056 0.2272 0.7896 0.108 Uiso 1 1 calc R . .
H28B H 0.4513 0.3031 0.7987 0.108 Uiso 1 1 calc R . .
H28C H 0.6383 0.3437 0.8066 0.108 Uiso 1 1 calc R . .
C29 C 0.9518(11) 0.7467(8) 0.5982(4) 0.165(4) Uani 1 1 d . . .
H29A H 1.0164 0.6917 0.6153 0.248 Uiso 1 1 calc R . .
H29B H 0.8374 0.7232 0.5916 0.248 Uiso 1 1 calc R . .
H29C H 0.9498 0.8063 0.6225 0.248 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
N1 C1 1.332(8) . ?
N1 C4 1.443(6) . ?
N1 C27 1.447(6) . ?
N2 C14 1.397(6) . ?
N2 C7 1.414(6) . ?
N2 C2 1.486(6) . ?
N3 C15 1.375(6) . ?
N3 C22 1.402(6) . ?
N3 C6 1.448(6) . ?
N4 C23 1.340(7) . ?
N4 C26 1.436(6) . ?
N4 H4 0.8600 . ?
O1 C1 1.367(7) . ?
O1 C3 1.447(6) . ?
O2 C1 1.213(7) . ?
O3 C6 1.422(6) . ?
O3 C2 1.429(6) . ?
O4 C23 1.251(6) . ?
O5 C29 1.358(8) . ?
O5 H5 0.8200 . ?
C2 C28 1.519(6) . ?
C2 C3 1.561(7) . ?
C3 C4 1.520(7) . ?
C3 H3 0.9800 . ?
C4 C5 1.510(6) . ?
C4 H4A 0.9800 . ?
C5 C6 1.537(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6 0.9800 . ?
C7 C8 1.401(7) . ?
C7 C12 1.407(6) . ?
C8 C9 1.396(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.391(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.356(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.438(7) . ?
C13 C14 1.418(6) . ?
C13 C24 1.420(6) . ?
C14 C15 1.405(7) . ?
C15 C16 1.404(6) . ?
C16 C25 1.401(6) . ?
C16 C17 1.440(7) . ?
C17 C22 1.400(7) . ?
C17 C18 1.410(7) . ?
C18 C19 1.372(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.385(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.380(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.399(7) . ?
C21 H21 0.9300 . ?
C23 C24 1.468(7) . ?
C24 C25 1.384(7) . ?
C25 C26 1.493(6) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 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
C1 N1 C4 112.4(5) . . ?
C1 N1 C27 122.6(5) . . ?
C4 N1 C27 123.7(5) . . ?
C14 N2 C7 105.9(4) . . ?
C14 N2 C2 125.7(4) . . ?
C7 N2 C2 123.8(4) . . ?
C15 N3 C22 108.5(4) . . ?
C15 N3 C6 121.7(4) . . ?
C22 N3 C6 129.3(5) . . ?
C23 N4 C26 113.4(4) . . ?
C23 N4 H4 123.3 . . ?
C26 N4 H4 123.3 . . ?
C1 O1 C3 107.8(5) . . ?
C6 O3 C2 120.1(4) . . ?
C29 O5 H5 109.5 . . ?
O2 C1 N1 128.8(7) . . ?
O2 C1 O1 120.7(7) . . ?
N1 C1 O1 110.4(6) . . ?
O3 C2 N2 110.2(4) . . ?
O3 C2 C28 102.3(4) . . ?
N2 C2 C28 111.1(4) . . ?
O3 C2 C3 106.7(4) . . ?
N2 C2 C3 113.8(4) . . ?
C28 C2 C3 112.1(4) . . ?
O1 C3 C4 105.7(4) . . ?
O1 C3 C2 111.5(4) . . ?
C4 C3 C2 116.3(5) . . ?
O1 C3 H3 107.7 . . ?
C4 C3 H3 107.7 . . ?
C2 C3 H3 107.7 . . ?
N1 C4 C5 113.1(4) . . ?
N1 C4 C3 100.7(4) . . ?
C5 C4 C3 110.5(4) . . ?
N1 C4 H4A 110.7 . . ?
C5 C4 H4A 110.7 . . ?
C3 C4 H4A 110.7 . . ?
C4 C5 C6 110.5(4) . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
O3 C6 N3 106.7(4) . . ?
O3 C6 C5 112.7(4) . . ?
N3 C6 C5 110.4(4) . . ?
O3 C6 H6 109.0 . . ?
N3 C6 H6 109.0 . . ?
C5 C6 H6 109.0 . . ?
C8 C7 C12 121.0(5) . . ?
C8 C7 N2 129.0(5) . . ?
C12 C7 N2 110.0(4) . . ?
C9 C8 C7 116.9(5) . . ?
C9 C8 H8 121.5 . . ?
C7 C8 H8 121.5 . . ?
C10 C9 C8 122.0(5) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C11 C10 C9 120.3(6) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.3(5) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 119.5(5) . . ?
C11 C12 C13 133.3(5) . . ?
C7 C12 C13 107.2(5) . . ?
C14 C13 C24 118.8(5) . . ?
C14 C13 C12 106.0(4) . . ?
C24 C13 C12 135.0(5) . . ?
N2 C14 C15 130.8(5) . . ?
N2 C14 C13 110.8(4) . . ?
C15 C14 C13 118.4(5) . . ?
N3 C15 C16 108.8(4) . . ?
N3 C15 C14 128.3(5) . . ?
C16 C15 C14 122.9(5) . . ?
C25 C16 C15 117.7(5) . . ?
C25 C16 C17 135.0(5) . . ?
C15 C16 C17 107.3(4) . . ?
C22 C17 C18 119.6(5) . . ?
C22 C17 C16 106.4(5) . . ?
C18 C17 C16 134.0(5) . . ?
C19 C18 C17 118.6(5) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C18 C19 C20 120.5(6) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C21 C20 C19 123.2(6) . . ?
C21 C20 H20 118.4 . . ?
C19 C20 H20 118.4 . . ?
C20 C21 C22 116.2(6) . . ?
C20 C21 H21 121.9 . . ?
C22 C21 H21 121.9 . . ?
C21 C22 C17 122.0(6) . . ?
C21 C22 N3 129.2(5) . . ?
C17 C22 N3 108.8(5) . . ?
O4 C23 N4 124.5(5) . . ?
O4 C23 C24 128.0(6) . . ?
N4 C23 C24 107.5(5) . . ?
C25 C24 C13 121.0(5) . . ?
C25 C24 C23 107.2(5) . . ?
C13 C24 C23 131.7(5) . . ?
C24 C25 C16 121.2(5) . . ?
C24 C25 C26 109.7(5) . . ?
C16 C25 C26 128.9(5) . . ?
N4 C26 C25 102.2(4) . . ?
N4 C26 H26A 111.3 . . ?
C25 C26 H26A 111.3 . . ?
N4 C26 H26B 111.3 . . ?
C25 C26 H26B 111.3 . . ?
H26A C26 H26B 109.2 . . ?
N1 C27 H27A 109.5 . . ?
N1 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N1 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C2 C28 H28A 109.5 . . ?
C2 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C2 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O5 C29 H29A 109.5 . . ?
O5 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O5 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
C4 N1 C1 O2 -173.3(6) . . . . ?
C27 N1 C1 O2 -6.2(9) . . . . ?
C4 N1 C1 O1 7.1(6) . . . . ?
C27 N1 C1 O1 174.2(4) . . . . ?
C3 O1 C1 O2 -174.9(5) . . . . ?
C3 O1 C1 N1 4.6(6) . . . . ?
C6 O3 C2 N2 65.8(5) . . . . ?
C6 O3 C2 C28 -176.0(4) . . . . ?
C6 O3 C2 C3 -58.2(5) . . . . ?
C14 N2 C2 O3 2.6(6) . . . . ?
C7 N2 C2 O3 155.3(4) . . . . ?
C14 N2 C2 C28 -110.0(5) . . . . ?
C7 N2 C2 C28 42.7(6) . . . . ?
C14 N2 C2 C3 122.4(5) . . . . ?
C7 N2 C2 C3 -84.9(5) . . . . ?
C1 O1 C3 C4 -13.6(5) . . . . ?
C1 O1 C3 C2 -140.9(4) . . . . ?
O3 C2 C3 O1 154.2(4) . . . . ?
N2 C2 C3 O1 32.5(6) . . . . ?
C28 C2 C3 O1 -94.6(5) . . . . ?
O3 C2 C3 C4 32.9(6) . . . . ?
N2 C2 C3 C4 -88.8(6) . . . . ?
C28 C2 C3 C4 144.1(5) . . . . ?
C1 N1 C4 C5 103.2(5) . . . . ?
C27 N1 C4 C5 -63.7(6) . . . . ?
C1 N1 C4 C3 -14.8(5) . . . . ?
C27 N1 C4 C3 178.3(4) . . . . ?
O1 C3 C4 N1 16.5(5) . . . . ?
C2 C3 C4 N1 140.8(4) . . . . ?
O1 C3 C4 C5 -103.3(5) . . . . ?
C2 C3 C4 C5 21.0(6) . . . . ?
N1 C4 C5 C6 -169.0(4) . . . . ?
C3 C4 C5 C6 -56.9(6) . . . . ?
C2 O3 C6 N3 -98.1(5) . . . . ?
C2 O3 C6 C5 23.2(6) . . . . ?
C15 N3 C6 O3 49.9(6) . . . . ?
C22 N3 C6 O3 -137.9(5) . . . . ?
C15 N3 C6 C5 -72.9(5) . . . . ?
C22 N3 C6 C5 99.3(6) . . . . ?
C4 C5 C6 O3 37.2(6) . . . . ?
C4 C5 C6 N3 156.3(4) . . . . ?
C14 N2 C7 C8 179.6(5) . . . . ?
C2 N2 C7 C8 22.3(7) . . . . ?
C14 N2 C7 C12 -2.2(5) . . . . ?
C2 N2 C7 C12 -159.4(4) . . . . ?
C12 C7 C8 C9 3.5(7) . . . . ?
N2 C7 C8 C9 -178.4(4) . . . . ?
C7 C8 C9 C10 -3.3(8) . . . . ?
C8 C9 C10 C11 1.3(8) . . . . ?
C9 C10 C11 C12 0.8(8) . . . . ?
C10 C11 C12 C7 -0.6(7) . . . . ?
C10 C11 C12 C13 177.5(5) . . . . ?
C8 C7 C12 C11 -1.6(7) . . . . ?
N2 C7 C12 C11 180.0(4) . . . . ?
C8 C7 C12 C13 179.9(4) . . . . ?
N2 C7 C12 C13 1.4(5) . . . . ?
C11 C12 C13 C14 -178.4(5) . . . . ?
C7 C12 C13 C14 -0.1(5) . . . . ?
C11 C12 C13 C24 7.0(10) . . . . ?
C7 C12 C13 C24 -174.8(5) . . . . ?
C7 N2 C14 C15 179.6(4) . . . . ?
C2 N2 C14 C15 -23.7(7) . . . . ?
C7 N2 C14 C13 2.1(5) . . . . ?
C2 N2 C14 C13 158.8(4) . . . . ?
C24 C13 C14 N2 174.5(4) . . . . ?
C12 C13 C14 N2 -1.2(5) . . . . ?
C24 C13 C14 C15 -3.4(6) . . . . ?
C12 C13 C14 C15 -179.1(4) . . . . ?
C22 N3 C15 C16 -0.9(5) . . . . ?
C6 N3 C15 C16 172.7(4) . . . . ?
C22 N3 C15 C14 179.8(4) . . . . ?
C6 N3 C15 C14 -6.5(7) . . . . ?
N2 C14 C15 N3 2.3(8) . . . . ?
C13 C14 C15 N3 179.6(4) . . . . ?
N2 C14 C15 C16 -176.8(5) . . . . ?
C13 C14 C15 C16 0.5(7) . . . . ?
N3 C15 C16 C25 -177.0(4) . . . . ?
C14 C15 C16 C25 2.2(7) . . . . ?
N3 C15 C16 C17 2.4(5) . . . . ?
C14 C15 C16 C17 -178.3(4) . . . . ?
C25 C16 C17 C22 176.4(5) . . . . ?
C15 C16 C17 C22 -2.9(5) . . . . ?
C25 C16 C17 C18 -1.7(9) . . . . ?
C15 C16 C17 C18 179.0(5) . . . . ?
C22 C17 C18 C19 0.9(7) . . . . ?
C16 C17 C18 C19 178.7(5) . . . . ?
C17 C18 C19 C20 -1.3(8) . . . . ?
C18 C19 C20 C21 0.6(9) . . . . ?
C19 C20 C21 C22 0.6(8) . . . . ?
C20 C21 C22 C17 -1.0(8) . . . . ?
C20 C21 C22 N3 178.4(5) . . . . ?
C18 C17 C22 C21 0.3(7) . . . . ?
C16 C17 C22 C21 -178.1(5) . . . . ?
C18 C17 C22 N3 -179.2(4) . . . . ?
C16 C17 C22 N3 2.4(5) . . . . ?
C15 N3 C22 C21 179.6(5) . . . . ?
C6 N3 C22 C21 6.6(9) . . . . ?
C15 N3 C22 C17 -1.0(5) . . . . ?
C6 N3 C22 C17 -174.0(4) . . . . ?
C26 N4 C23 O4 179.0(5) . . . . ?
C26 N4 C23 C24 -0.4(6) . . . . ?
C14 C13 C24 C25 3.6(7) . . . . ?
C12 C13 C24 C25 177.7(5) . . . . ?
C14 C13 C24 C23 -173.0(4) . . . . ?
C12 C13 C24 C23 1.1(9) . . . . ?
O4 C23 C24 C25 179.4(5) . . . . ?
N4 C23 C24 C25 -1.2(5) . . . . ?
O4 C23 C24 C13 -3.7(8) . . . . ?
N4 C23 C24 C13 175.7(5) . . . . ?
C13 C24 C25 C16 -0.8(7) . . . . ?
C23 C24 C25 C16 176.6(4) . . . . ?
C13 C24 C25 C26 -175.0(4) . . . . ?
C23 C24 C25 C26 2.3(5) . . . . ?
C15 C16 C25 C24 -2.1(6) . . . . ?
C17 C16 C25 C24 178.6(5) . . . . ?
C15 C16 C25 C26 171.0(5) . . . . ?
C17 C16 C25 C26 -8.3(9) . . . . ?
C23 N4 C26 C25 1.7(6) . . . . ?
C24 C25 C26 N4 -2.4(5) . . . . ?
C16 C25 C26 N4 -176.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.037



_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_110108d
_database_code_depnum_ccdc_archive 'CCDC 2168509'
loop_
_audit_author_name
_audit_author_address
'Liping Wang'
;Guizhou Medcial University
China
;

_audit_update_record             
;
2022-04-25 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;
# ----------------------------------------------------------------------------

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H28 N4 O5'
_chemical_formula_weight         524.56

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.6137(9)
_cell_length_b                   12.9897(14)
_cell_length_c                   25.647(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2536.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2730
_cell_measurement_theta_min      2.791
_cell_measurement_theta_max      26.172

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9656
_exptl_absorpt_correction_T_max  0.9794
_exptl_absorpt_process_details   sadabs

_exptl_special_details           ?

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10497
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2569
_reflns_number_gt                1815
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0698P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(10)
_refine_ls_number_reflns         2569
_refine_ls_number_parameters     366
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1147
_refine_ls_wR_factor_gt          0.1036
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_restrained_S_all      0.977
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.9017(6) 0.3109(3) 0.96319(14) 0.0777(11) Uani 1 1 d . . .
H1 H 0.9177 0.2545 0.9801 0.093 Uiso 1 1 calc R . .
N2 N 0.9718(4) 0.6639(2) 0.81971(11) 0.0463(7) Uani 1 1 d . . .
N3 N 0.6098(4) 0.6940(2) 0.88039(11) 0.0519(8) Uani 1 1 d . . .
N4 N 1.0415(5) 0.9604(2) 0.84746(12) 0.0598(9) Uani 1 1 d . . .
O1 O 0.6334(5) 0.3526(2) 0.99925(12) 0.0838(10) Uani 1 1 d . . .
O2 O 0.6971(3) 0.74182(18) 0.79778(9) 0.0511(6) Uani 1 1 d . . .
O3 O 1.1319(4) 0.85617(19) 0.78559(11) 0.0646(7) Uani 1 1 d . . .
O4 O 1.3343(4) 0.9496(2) 0.82786(13) 0.0746(9) Uani 1 1 d . . .
O5 O 0.5685(8) 0.0513(5) 0.8953(3) 0.195(3) Uani 1 1 d . A .
H5 H 0.4837 0.0307 0.8786 0.293 Uiso 1 1 calc R . .
C1 C 0.7570(7) 0.3699(3) 0.96931(17) 0.0655(12) Uani 1 1 d . . .
C2 C 0.7780(6) 0.4569(3) 0.93199(14) 0.0534(10) Uani 1 1 d . . .
C3 C 0.9359(5) 0.4457(3) 0.90662(15) 0.0540(10) Uani 1 1 d . . .
C4 C 1.0269(6) 0.3502(3) 0.92613(17) 0.0682(12) Uani 1 1 d . . .
H4A H 1.0474 0.3015 0.8981 0.082 Uiso 1 1 calc R . .
H4B H 1.1378 0.3667 0.9428 0.082 Uiso 1 1 calc R . .
C5 C 0.8873(5) 0.6015(3) 0.85739(13) 0.0470(9) Uani 1 1 d . . .
C6 C 0.9934(5) 0.5162(2) 0.86893(14) 0.0482(9) Uani 1 1 d . . .
C7 C 1.1473(5) 0.5240(3) 0.83724(14) 0.0497(9) Uani 1 1 d . . .
C8 C 1.1303(5) 0.6133(2) 0.80674(14) 0.0485(9) Uani 1 1 d . . .
C9 C 1.2614(5) 0.6394(3) 0.77102(15) 0.0576(10) Uani 1 1 d . . .
H9 H 1.2527 0.6989 0.7510 0.069 Uiso 1 1 calc R . .
C10 C 1.4040(6) 0.5748(3) 0.76612(17) 0.0677(12) Uani 1 1 d . . .
H10 H 1.4908 0.5904 0.7419 0.081 Uiso 1 1 calc R . .
C11 C 1.4213(6) 0.4863(3) 0.79676(18) 0.0712(12) Uani 1 1 d . . .
H11 H 1.5192 0.4442 0.7927 0.085 Uiso 1 1 calc R . .
C12 C 1.2961(5) 0.4614(3) 0.83239(17) 0.0612(11) Uani 1 1 d . . .
H12 H 1.3091 0.4034 0.8533 0.073 Uiso 1 1 calc R . .
C13 C 0.7298(5) 0.6141(3) 0.88449(13) 0.0486(9) Uani 1 1 d . . .
C14 C 0.6699(5) 0.5428(3) 0.92176(13) 0.0511(9) Uani 1 1 d . . .
C15 C 0.5035(5) 0.5817(3) 0.94016(14) 0.0524(10) Uani 1 1 d . . .
C16 C 0.4720(5) 0.6763(3) 0.91422(13) 0.0499(9) Uani 1 1 d . . .
C17 C 0.3243(6) 0.7357(3) 0.92446(16) 0.0651(11) Uani 1 1 d . . .
H17 H 0.3069 0.7987 0.9079 0.078 Uiso 1 1 calc R . .
C18 C 0.2043(6) 0.6982(4) 0.95996(16) 0.0721(12) Uani 1 1 d . . .
H18 H 0.1048 0.7369 0.9675 0.087 Uiso 1 1 calc R . .
C19 C 0.2274(6) 0.6046(4) 0.98476(16) 0.0733(13) Uani 1 1 d . . .
H19 H 0.1428 0.5808 1.0080 0.088 Uiso 1 1 calc R . .
C20 C 0.3751(6) 0.5467(3) 0.97523(14) 0.0644(11) Uani 1 1 d . . .
H20 H 0.3900 0.4840 0.9921 0.077 Uiso 1 1 calc R . .
C21 C 0.8770(5) 0.7361(3) 0.78364(14) 0.0470(9) Uani 1 1 d . . .
C22 C 0.9440(5) 0.8477(3) 0.78480(14) 0.0515(10) Uani 1 1 d . . .
H22 H 0.9028 0.8812 0.7528 0.062 Uiso 1 1 calc R . .
C23 C 0.8792(5) 0.9124(3) 0.83062(15) 0.0522(9) Uani 1 1 d . . .
H23 H 0.7966 0.9649 0.8184 0.063 Uiso 1 1 calc R . .
C24 C 0.7938(5) 0.8465(3) 0.87190(14) 0.0506(9) Uani 1 1 d . . .
H24A H 0.8813 0.8022 0.8878 0.061 Uiso 1 1 calc R . .
H24B H 0.7447 0.8901 0.8989 0.061 Uiso 1 1 calc R . .
C25 C 0.6508(5) 0.7819(3) 0.84822(13) 0.0512(9) Uani 1 1 d . . .
H25 H 0.5450 0.8242 0.8446 0.061 Uiso 1 1 calc R . .
C26 C 1.1819(6) 0.9255(3) 0.82201(17) 0.0545(10) Uani 1 1 d . . .
C27 C 0.8758(6) 0.6932(3) 0.72868(14) 0.0641(11) Uani 1 1 d . . .
H27A H 0.7960 0.7323 0.7075 0.096 Uiso 1 1 calc R . .
H27B H 0.8388 0.6225 0.7295 0.096 Uiso 1 1 calc R . .
H27C H 0.9918 0.6974 0.7142 0.096 Uiso 1 1 calc R . .
C28 C 1.0529(7) 1.0312(4) 0.8910(2) 0.0944(16) Uani 1 1 d . . .
H28A H 1.1361 1.0844 0.8831 0.142 Uiso 1 1 calc R . .
H28B H 1.0904 0.9946 0.9216 0.142 Uiso 1 1 calc R . .
H28C H 0.9397 1.0613 0.8973 0.142 Uiso 1 1 calc R . .
C29 C 0.5452(11) 0.1535(6) 0.9077(3) 0.149(3) Uani 1 1 d . . .
H29A H 0.6193 0.1708 0.9371 0.179 Uiso 0.745(16) 1 calc PR A 1
H29B H 0.4240 0.1645 0.9180 0.179 Uiso 0.745(16) 1 calc PR A 1
H29C H 0.5678 0.1591 0.9448 0.179 Uiso 0.255(16) 1 d PR A 2
H29D H 0.6433 0.1875 0.8908 0.179 Uiso 0.255(16) 1 d PR A 2
C30 C 0.5876(19) 0.2222(7) 0.8637(5) 0.140(6) Uani 0.745(16) 1 d P A 1
H30A H 0.5087 0.2089 0.8353 0.209 Uiso 0.745(16) 1 calc PR A 1
H30B H 0.7062 0.2099 0.8526 0.209 Uiso 0.745(16) 1 calc PR A 1
H30C H 0.5757 0.2926 0.8746 0.209 Uiso 0.745(16) 1 calc PR A 1
C30' C 0.392(5) 0.2228(17) 0.8979(11) 0.134(16) Uani 0.255(16) 1 d P A 2
H30D H 0.2981 0.1839 0.8828 0.201 Uiso 0.255(16) 1 calc PR A 2
H30E H 0.4266 0.2766 0.8744 0.201 Uiso 0.255(16) 1 calc PR A 2
H30F H 0.3542 0.2524 0.9303 0.201 Uiso 0.255(16) 1 calc PR 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
N1 C1 1.351(6) . ?
N1 C4 1.439(6) . ?
N1 H1 0.8600 . ?
N2 C8 1.414(5) . ?
N2 C5 1.416(4) . ?
N2 C21 1.503(4) . ?
N3 C16 1.380(5) . ?
N3 C13 1.387(4) . ?
N3 C25 1.442(4) . ?
N4 C26 1.332(5) . ?
N4 C23 1.450(5) . ?
N4 C28 1.450(5) . ?
O1 C1 1.235(5) . ?
O2 C21 1.419(5) . ?
O2 C25 1.438(4) . ?
O3 C26 1.352(5) . ?
O3 C22 1.435(5) . ?
O4 C26 1.212(5) . ?
O5 C29 1.376(8) . ?
O5 H5 0.8200 . ?
C1 C2 1.490(5) . ?
C2 C3 1.374(6) . ?
C2 C14 1.411(5) . ?
C3 C6 1.402(5) . ?
C3 C4 1.506(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C13 1.396(5) . ?
C5 C6 1.403(5) . ?
C6 C7 1.430(5) . ?
C7 C12 1.400(5) . ?
C7 C8 1.405(5) . ?
C8 C9 1.397(5) . ?
C9 C10 1.378(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.398(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.360(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.407(5) . ?
C14 C15 1.443(5) . ?
C15 C20 1.404(5) . ?
C15 C16 1.417(5) . ?
C16 C17 1.390(6) . ?
C17 C18 1.379(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.374(6) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C27 1.516(5) . ?
C21 C22 1.536(5) . ?
C22 C23 1.526(5) . ?
C22 H22 0.9800 . ?
C23 C24 1.509(5) . ?
C23 H23 0.9800 . ?
C24 C25 1.503(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25 0.9800 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.474(13) . ?
C29 C30' 1.49(3) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 H29C 0.9700 . ?
C29 H29D 0.9700 . ?
C30 H29D 0.9303 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C30' H30D 0.9600 . ?
C30' H30E 0.9600 . ?
C30' H30F 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
C1 N1 C4 114.5(4) . . ?
C1 N1 H1 122.7 . . ?
C4 N1 H1 122.7 . . ?
C8 N2 C5 106.4(3) . . ?
C8 N2 C21 123.8(3) . . ?
C5 N2 C21 124.0(3) . . ?
C16 N3 C13 109.1(3) . . ?
C16 N3 C25 131.0(3) . . ?
C13 N3 C25 119.5(3) . . ?
C26 N4 C23 113.0(3) . . ?
C26 N4 C28 123.1(4) . . ?
C23 N4 C28 123.6(3) . . ?
C21 O2 C25 119.0(3) . . ?
C26 O3 C22 110.0(3) . . ?
C29 O5 H5 109.5 . . ?
O1 C1 N1 126.2(4) . . ?
O1 C1 C2 128.3(4) . . ?
N1 C1 C2 105.5(4) . . ?
C3 C2 C14 120.4(3) . . ?
C3 C2 C1 108.5(4) . . ?
C14 C2 C1 131.0(4) . . ?
C2 C3 C6 122.0(4) . . ?
C2 C3 C4 109.4(3) . . ?
C6 C3 C4 128.6(4) . . ?
N1 C4 C3 101.9(4) . . ?
N1 C4 H4A 111.4 . . ?
C3 C4 H4A 111.4 . . ?
N1 C4 H4B 111.4 . . ?
C3 C4 H4B 111.4 . . ?
H4A C4 H4B 109.2 . . ?
C13 C5 C6 118.8(3) . . ?
C13 C5 N2 131.5(3) . . ?
C6 C5 N2 109.5(3) . . ?
C3 C6 C5 118.8(4) . . ?
C3 C6 C7 134.0(3) . . ?
C5 C6 C7 107.2(3) . . ?
C12 C7 C8 120.3(4) . . ?
C12 C7 C6 132.3(3) . . ?
C8 C7 C6 107.4(3) . . ?
C9 C8 C7 120.0(3) . . ?
C9 C8 N2 130.7(3) . . ?
C7 C8 N2 109.4(3) . . ?
C10 C9 C8 118.4(4) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C9 C10 C11 121.6(4) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C12 C11 C10 120.5(4) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C7 119.3(4) . . ?
C11 C12 H12 120.4 . . ?
C7 C12 H12 120.4 . . ?
N3 C13 C5 128.0(3) . . ?
N3 C13 C14 109.3(3) . . ?
C5 C13 C14 122.6(3) . . ?
C13 C14 C2 117.2(4) . . ?
C13 C14 C15 106.0(3) . . ?
C2 C14 C15 136.8(3) . . ?
C20 C15 C16 117.6(4) . . ?
C20 C15 C14 135.0(4) . . ?
C16 C15 C14 107.4(3) . . ?
N3 C16 C17 129.9(4) . . ?
N3 C16 C15 108.2(3) . . ?
C17 C16 C15 122.0(4) . . ?
C18 C17 C16 117.7(4) . . ?
C18 C17 H17 121.2 . . ?
C16 C17 H17 121.2 . . ?
C17 C18 C19 122.0(5) . . ?
C17 C18 H18 119.0 . . ?
C19 C18 H18 119.0 . . ?
C20 C19 C18 120.2(4) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C15 120.4(4) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
O2 C21 N2 109.8(3) . . ?
O2 C21 C27 104.6(3) . . ?
N2 C21 C27 110.2(3) . . ?
O2 C21 C22 105.5(3) . . ?
N2 C21 C22 114.6(3) . . ?
C27 C21 C22 111.6(3) . . ?
O3 C22 C23 105.6(3) . . ?
O3 C22 C21 113.8(3) . . ?
C23 C22 C21 115.3(3) . . ?
O3 C22 H22 107.2 . . ?
C23 C22 H22 107.2 . . ?
C21 C22 H22 107.2 . . ?
N4 C23 C24 113.7(3) . . ?
N4 C23 C22 101.0(3) . . ?
C24 C23 C22 111.5(3) . . ?
N4 C23 H23 110.1 . . ?
C24 C23 H23 110.1 . . ?
C22 C23 H23 110.1 . . ?
C25 C24 C23 110.2(3) . . ?
C25 C24 H24A 109.6 . . ?
C23 C24 H24A 109.6 . . ?
C25 C24 H24B 109.6 . . ?
C23 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
O2 C25 N3 106.4(3) . . ?
O2 C25 C24 112.8(3) . . ?
N3 C25 C24 111.6(3) . . ?
O2 C25 H25 108.7 . . ?
N3 C25 H25 108.7 . . ?
C24 C25 H25 108.7 . . ?
O4 C26 N4 128.3(4) . . ?
O4 C26 O3 121.9(4) . . ?
N4 C26 O3 109.9(3) . . ?
C21 C27 H27A 109.5 . . ?
C21 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C21 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N4 C28 H28A 109.5 . . ?
N4 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N4 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O5 C29 C30 112.3(7) . . ?
O5 C29 C30' 130.1(12) . . ?
C30 C29 C30' 71.2(13) . . ?
O5 C29 H29A 109.1 . . ?
C30 C29 H29A 109.1 . . ?
C30' C29 H29A 116.4 . . ?
O5 C29 H29B 109.1 . . ?
C30 C29 H29B 109.1 . . ?
C30' C29 H29B 38.3 . . ?
H29A C29 H29B 107.9 . . ?
O5 C29 H29C 106.0 . . ?
C30 C29 H29C 131.8 . . ?
C30' C29 H29C 104.9 . . ?
H29A C29 H29C 27.7 . . ?
H29B C29 H29C 83.7 . . ?
O5 C29 H29D 103.7 . . ?
C30 C29 H29D 38.2 . . ?
C30' C29 H29D 104.6 . . ?
H29A C29 H29D 78.1 . . ?
H29B C29 H29D 141.9 . . ?
H29C C29 H29D 105.5 . . ?
C29 C30 H29D 40.1 . . ?
C29 C30 H30A 109.5 . . ?
H29D C30 H30A 139.8 . . ?
C29 C30 H30B 109.5 . . ?
H29D C30 H30B 73.3 . . ?
C29 C30 H30C 109.5 . . ?
H29D C30 H30C 106.7 . . ?
C29 C30' H30D 109.5 . . ?
C29 C30' H30E 109.5 . . ?
H30D C30' H30E 109.5 . . ?
C29 C30' H30F 109.5 . . ?
H30D C30' H30F 109.5 . . ?
H30E C30' H30F 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
C4 N1 C1 O1 -179.0(4) . . . . ?
C4 N1 C1 C2 2.1(5) . . . . ?
O1 C1 C2 C3 180.0(4) . . . . ?
N1 C1 C2 C3 -1.2(4) . . . . ?
O1 C1 C2 C14 2.2(7) . . . . ?
N1 C1 C2 C14 -178.9(4) . . . . ?
C14 C2 C3 C6 -1.8(5) . . . . ?
C1 C2 C3 C6 -179.9(3) . . . . ?
C14 C2 C3 C4 178.0(3) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C1 N1 C4 C3 -2.1(5) . . . . ?
C2 C3 C4 N1 1.2(4) . . . . ?
C6 C3 C4 N1 -179.0(4) . . . . ?
C8 N2 C5 C13 178.7(4) . . . . ?
C21 N2 C5 C13 -27.5(5) . . . . ?
C8 N2 C5 C6 2.0(4) . . . . ?
C21 N2 C5 C6 155.8(3) . . . . ?
C2 C3 C6 C5 0.9(5) . . . . ?
C4 C3 C6 C5 -178.9(4) . . . . ?
C2 C3 C6 C7 179.8(4) . . . . ?
C4 C3 C6 C7 0.0(7) . . . . ?
C13 C5 C6 C3 1.1(5) . . . . ?
N2 C5 C6 C3 178.3(3) . . . . ?
C13 C5 C6 C7 -178.1(3) . . . . ?
N2 C5 C6 C7 -0.9(4) . . . . ?
C3 C6 C7 C12 1.1(7) . . . . ?
C5 C6 C7 C12 -180.0(4) . . . . ?
C3 C6 C7 C8 -179.6(4) . . . . ?
C5 C6 C7 C8 -0.7(4) . . . . ?
C12 C7 C8 C9 0.6(5) . . . . ?
C6 C7 C8 C9 -178.8(3) . . . . ?
C12 C7 C8 N2 -178.7(3) . . . . ?
C6 C7 C8 N2 1.9(4) . . . . ?
C5 N2 C8 C9 178.4(4) . . . . ?
C21 N2 C8 C9 24.5(5) . . . . ?
C5 N2 C8 C7 -2.5(4) . . . . ?
C21 N2 C8 C7 -156.3(3) . . . . ?
C7 C8 C9 C10 1.1(5) . . . . ?
N2 C8 C9 C10 -179.8(3) . . . . ?
C8 C9 C10 C11 -1.6(6) . . . . ?
C9 C10 C11 C12 0.3(6) . . . . ?
C10 C11 C12 C7 1.5(6) . . . . ?
C8 C7 C12 C11 -1.9(5) . . . . ?
C6 C7 C12 C11 177.3(4) . . . . ?
C16 N3 C13 C5 180.0(3) . . . . ?
C25 N3 C13 C5 -5.9(5) . . . . ?
C16 N3 C13 C14 -0.1(4) . . . . ?
C25 N3 C13 C14 174.0(3) . . . . ?
C6 C5 C13 N3 177.6(3) . . . . ?
N2 C5 C13 N3 1.2(6) . . . . ?
C6 C5 C13 C14 -2.2(5) . . . . ?
N2 C5 C13 C14 -178.6(3) . . . . ?
N3 C13 C14 C2 -178.6(3) . . . . ?
C5 C13 C14 C2 1.3(5) . . . . ?
N3 C13 C14 C15 1.0(4) . . . . ?
C5 C13 C14 C15 -179.1(3) . . . . ?
C3 C2 C14 C13 0.8(5) . . . . ?
C1 C2 C14 C13 178.3(4) . . . . ?
C3 C2 C14 C15 -178.7(4) . . . . ?
C1 C2 C14 C15 -1.2(7) . . . . ?
C13 C14 C15 C20 177.4(4) . . . . ?
C2 C14 C15 C20 -3.2(7) . . . . ?
C13 C14 C15 C16 -1.5(4) . . . . ?
C2 C14 C15 C16 178.0(4) . . . . ?
C13 N3 C16 C17 178.4(4) . . . . ?
C25 N3 C16 C17 5.2(6) . . . . ?
C13 N3 C16 C15 -0.8(4) . . . . ?
C25 N3 C16 C15 -174.1(3) . . . . ?
C20 C15 C16 N3 -177.6(3) . . . . ?
C14 C15 C16 N3 1.4(4) . . . . ?
C20 C15 C16 C17 3.0(5) . . . . ?
C14 C15 C16 C17 -177.9(3) . . . . ?
N3 C16 C17 C18 178.9(4) . . . . ?
C15 C16 C17 C18 -2.0(6) . . . . ?
C16 C17 C18 C19 -0.3(6) . . . . ?
C17 C18 C19 C20 1.3(6) . . . . ?
C18 C19 C20 C15 -0.2(6) . . . . ?
C16 C15 C20 C19 -1.9(5) . . . . ?
C14 C15 C20 C19 179.4(4) . . . . ?
C25 O2 C21 N2 62.9(4) . . . . ?
C25 O2 C21 C27 -178.9(3) . . . . ?
C25 O2 C21 C22 -61.1(4) . . . . ?
C8 N2 C21 O2 157.0(3) . . . . ?
C5 N2 C21 O2 7.6(4) . . . . ?
C8 N2 C21 C27 42.3(4) . . . . ?
C5 N2 C21 C27 -107.0(4) . . . . ?
C8 N2 C21 C22 -84.5(4) . . . . ?
C5 N2 C21 C22 126.1(3) . . . . ?
C26 O3 C22 C23 -6.5(4) . . . . ?
C26 O3 C22 C21 -134.0(3) . . . . ?
O2 C21 C22 O3 163.9(3) . . . . ?
N2 C21 C22 O3 43.0(4) . . . . ?
C27 C21 C22 O3 -83.2(4) . . . . ?
O2 C21 C22 C23 41.7(4) . . . . ?
N2 C21 C22 C23 -79.3(4) . . . . ?
C27 C21 C22 C23 154.6(4) . . . . ?
C26 N4 C23 C24 113.7(4) . . . . ?
C28 N4 C23 C24 -60.3(5) . . . . ?
C26 N4 C23 C22 -5.9(4) . . . . ?
C28 N4 C23 C22 -179.9(4) . . . . ?
O3 C22 C23 N4 7.1(4) . . . . ?
C21 C22 C23 N4 133.7(3) . . . . ?
O3 C22 C23 C24 -114.0(3) . . . . ?
C21 C22 C23 C24 12.5(5) . . . . ?
N4 C23 C24 C25 -167.6(3) . . . . ?
C22 C23 C24 C25 -54.2(4) . . . . ?
C21 O2 C25 N3 -102.2(3) . . . . ?
C21 O2 C25 C24 20.4(4) . . . . ?
C16 N3 C25 O2 -134.4(3) . . . . ?
C13 N3 C25 O2 53.0(4) . . . . ?
C16 N3 C25 C24 102.2(4) . . . . ?
C13 N3 C25 C24 -70.4(4) . . . . ?
C23 C24 C25 O2 39.7(4) . . . . ?
C23 C24 C25 N3 159.3(3) . . . . ?
C23 N4 C26 O4 -179.0(4) . . . . ?
C28 N4 C26 O4 -4.9(7) . . . . ?
C23 N4 C26 O3 2.1(4) . . . . ?
C28 N4 C26 O3 176.2(4) . . . . ?
C22 O3 C26 O4 -176.0(4) . . . . ?
C22 O3 C26 N4 3.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.034



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