# 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_phznprop
_audit_block_doi                 10.5517/ccdc.csd.cc27f9qq
_database_code_depnum_ccdc_archive 'CCDC 2068373'
loop_
_audit_author_name
_audit_author_address
'Bruce Foxman'
;Brandeis Univ
United States of America
;
_audit_update_record             
;
2021-03-05 deposited with the CCDC.	2021-04-14 downloaded from the CCDC.
;
_audit_creation_date             2021-03-05
_audit_creation_method           'CRYSTALS_ver_14.61_build_7986 '

_oxford_structure_analysis_title PHENANZPROP
_chemical_name_systematic        .
_chemical_melting_point          'not measured'
_cell_length_a                   3.8373(10)
_cell_length_b                   20.9685(10)
_cell_length_c                   9.8459(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.765(10)
_cell_angle_gamma                90
_cell_volume                     789.5(2)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C9 H6 N1 O2 
# Dc =      1.35 Fooo =    332.00 Mu =      8.08 M =    160.15
# Found Formula = C9 H6 N1 O2 
# Dc =      1.35 FOOO =    332.00 Mu =      8.08 M =    160.15

_chemical_formula_sum            'C9 H6 N1 O2'
_chemical_formula_moiety         'C9 H6 N1 O2'
_chemical_compound_source        .
_chemical_formula_weight         160.15


_cell_measurement_reflns_used    25
_cell_measurement_theta_min      38.00
_cell_measurement_theta_max      45.00
_cell_measurement_temperature    294

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.120
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_max          0.350

_exptl_crystal_density_diffrn    1.347
# Non-dispersive F(000): 
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    0.808

# Sheldrick geometric approximatio 0.84 0.91 
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.91
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_device       Serial
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'CAD4 EXPRESS, (Straver, 1992)'
_computing_cell_refinement       'CAD4 EXPRESS, (Straver, 1992)'
_computing_data_reduction        'RC93 (Watkin et al., 1994)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  7200
_diffrn_standards_interval_count .
_diffrn_standards_number         3
_diffrn_standards_decay_%        0.00

_diffrn_ambient_temperature      294
_diffrn_reflns_number            1908
_reflns_number_total             1606
_diffrn_reflns_av_R_equivalents  0.011
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1606 
# Theoretical number of reflections is about 3208 


_diffrn_reflns_theta_min         4.217
_diffrn_reflns_theta_max         74.042
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        74.042
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_reflns_limit_h_min              0
_reflns_limit_h_max              4
_reflns_limit_k_min              0
_reflns_limit_k_max              26
_reflns_limit_l_min              -12
_reflns_limit_l_max              12

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.14
_refine_diff_density_max         0.15


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>2.0\s(I)
_refine_ls_number_restraints     2
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1402
_refine_ls_R_factor_ref          0.0405
_refine_ls_wR_factor_ref         0.0558
_refine_ls_goodness_of_fit_ref   1.0175
_refine_ls_shift/su_max          0.0003477
_refine_ls_shift/su_mean         0.0000313


# Computed with I/sigma = -10 
_reflns_number_all               1606
_refine_ls_R_factor_all          0.0459
_refine_ls_wR_factor_all         0.0755

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1402
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_gt          0.0558


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method = Chebychev polynomial, (Carruthers & Watkin, 1979) 
 W = 1.0/[A[0]*T[0]'(X)+A[1]*T[1]'(X) ... +A[NP-1]*T[NP-1]'(X)] 
 16.1 18.8 3.76 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.1244(3) 0.45712(6) 0.10275(12) 0.0475 1.0000 Uani . . . . . .
O1 O 0.5532(4) 0.60616(6) 0.67860(13) 0.0692 1.0000 Uani D . . . . .
O2 O 0.7114(4) 0.69886(6) 0.77170(12) 0.0744 1.0000 Uani . . . . . .
C1 C -0.2039(5) 0.58494(8) 0.30401(18) 0.0607 1.0000 Uani . . . . . .
C2 C -0.0580(5) 0.52880(8) 0.27287(16) 0.0551 1.0000 Uani . . . . . .
C3 C -0.0238(4) 0.51260(7) 0.13397(15) 0.0450 1.0000 Uani . . . . . .
C4 C 0.1487(4) 0.44340(7) -0.02975(15) 0.0456 1.0000 Uani . . . . . .
C5 C 0.2986(4) 0.38493(7) -0.06760(17) 0.0548 1.0000 Uani . . . . . .
C6 C 0.3227(5) 0.37111(8) -0.20117(19) 0.0611 1.0000 Uani . . . . . .
C7 C 0.5628(4) 0.66811(7) 0.68199(15) 0.0485 1.0000 Uani . . . . . .
C8 C 0.3749(4) 0.69753(8) 0.56484(17) 0.0524 1.0000 Uani . . . . . .
C9 C 0.2194(5) 0.72431(9) 0.47412(19) 0.0668 1.0000 Uani . . . . . .
H1 H 0.677(6) 0.5926(12) 0.752(2) 0.105(2) 1.0000 Uiso D . . . . .
H2 H 0.0234 0.4989 0.3409 0.0650 1.0000 Uiso R . . . . .
H6 H 0.4237 0.3310 -0.2268 0.0727 1.0000 Uiso R . . . . .
H11 H -0.2285 0.5949 0.3933 0.0734 1.0000 Uiso R . . . . .
H41 H 0.3758 0.3552 -0.0003 0.0666 1.0000 Uiso R . . . . .
H91 H 0.0888 0.7474 0.4022 0.0807 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       435(19)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          4.77(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C3 . 1.3418(19) yes
N1 . C4 . 1.347(2) yes
O1 . C7 . 1.2999(19) yes
O1 . H1 . 0.876(16) no
O2 . C7 . 1.1989(19) yes
C1 . C6 2_565 1.416(3) yes
C1 . C2 . 1.349(2) yes
C1 . H11 . 0.916 no
C2 . C3 . 1.426(2) yes
C2 . H2 . 0.950 no
C3 . C4 2_565 1.432(2) yes
C4 . C5 . 1.417(2) yes
C5 . C6 . 1.357(2) yes
C5 . H41 . 0.939 no
C6 . H6 . 0.968 no
C7 . C8 . 1.447(2) yes
C8 . C9 . 1.175(2) yes
C9 . H91 . 0.964 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 . N1 . C4 . 118.16(13) yes
C7 . O1 . H1 . 106.9(17) no
C6 2_565 C1 . C2 . 121.34(16) yes
C6 2_565 C1 . H11 . 119.0 no
C2 . C1 . H11 . 119.6 no
C1 . C2 . C3 . 119.91(15) yes
C1 . C2 . H2 . 122.2 no
C3 . C2 . H2 . 117.9 no
C4 2_565 C3 . C2 . 118.80(14) yes
C4 2_565 C3 . N1 . 121.15(13) yes
C2 . C3 . N1 . 120.05(14) yes
C3 2_565 C4 . N1 . 120.69(13) yes
C3 2_565 C4 . C5 . 119.19(14) yes
N1 . C4 . C5 . 120.12(14) yes
C4 . C5 . C6 . 120.09(15) yes
C4 . C5 . H41 . 120.0 no
C6 . C5 . H41 . 119.9 no
C1 2_565 C6 . C5 . 120.67(16) yes
C1 2_565 C6 . H6 . 119.4 no
C5 . C6 . H6 . 120.0 no
O1 . C7 . O2 . 124.54(15) yes
O1 . C7 . C8 . 113.23(13) yes
O2 . C7 . C8 . 122.23(15) yes
C7 . C8 . C9 . 176.29(19) yes
C8 . C9 . H91 . 177.8 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O1 . H1 . N1 2_666 164(2) 0.876(16) 1.881(17) 2.736(2) yes
C5 . H41 . O2 2_666 149 0.94 2.57 3.405(2) yes
C9 . H91 . O2 4_464 168 0.96 2.17 3.118(2) yes



_refine_special_details          
;
?
  Reflections are selected by the following conditions :-
  Minimum value of RATIO        is   1.96
;
####################################################################### 
# 
# 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_001zy19s
_database_code_depnum_ccdc_archive 'CCDC 2069372'
loop_
_audit_author_name
_audit_author_address
'Zongyao Zhang'
;Renmin University of China
China
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C45 H42 I2 N8 O6.20'
_chemical_formula_weight         1047.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   25.3739(2)
_cell_length_b                   27.4143(2)
_cell_length_c                   14.36510(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.1990(10)
_cell_angle_gamma                90
_cell_volume                     9642.95(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    28060
_cell_measurement_theta_min      3.5730
_cell_measurement_theta_max      75.9460

_exptl_crystal_description       sphere
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             4189
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_rad          0.300
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    10.681
_shelx_estimated_absorpt_T_min   0.142
_shelx_estimated_absorpt_T_max   0.224
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_correction_T_min  0.01028
_exptl_absorpt_correction_T_max  0.08176
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Spherical absorption correction 
 using equivalent radius and absorption coefficient. 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4102
_diffrn_reflns_number            59983
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.606
_diffrn_reflns_theta_max         76.207
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10028
_reflns_number_gt                9257
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10028
_refine_ls_number_parameters     561
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0810
_refine_ls_wR_factor_ref         0.2347
_refine_ls_wR_factor_gt          0.2274
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8845(4) 0.8261(4) 0.7205(5) 0.116(3) Uani 1 1 d . . . . .
H1A H 0.8954 0.8540 0.6896 0.175 Uiso 1 1 calc R U . . .
H1B H 0.9084 0.7992 0.7181 0.175 Uiso 1 1 calc R U . . .
H1C H 0.8866 0.8338 0.7865 0.175 Uiso 1 1 calc R U . . .
C2 C 0.8256(3) 0.8121(2) 0.6681(4) 0.0806(13) Uani 1 1 d . . . . .
C3 C 0.7898(8) 0.8471(8) 0.6987(7) 0.197(9) Uani 1 1 d . . . . .
H3A H 0.7536 0.8450 0.6563 0.296 Uiso 1 1 calc R U . . .
H3B H 0.8037 0.8795 0.6965 0.296 Uiso 1 1 calc R U . . .
H3C H 0.7885 0.8397 0.7634 0.296 Uiso 1 1 calc R U . . .
C4 C 0.8189(5) 0.7591(4) 0.6978(6) 0.129(4) Uani 1 1 d . . . . .
H4A H 0.8292 0.7566 0.7668 0.193 Uiso 1 1 calc R U . . .
H4B H 0.8420 0.7382 0.6717 0.193 Uiso 1 1 calc R U . . .
H4C H 0.7816 0.7492 0.6732 0.193 Uiso 1 1 calc R U . . .
C5 C 0.8190(2) 0.8136(2) 0.5583(4) 0.0706(10) Uani 1 1 d . . . . .
C6 C 0.7782(2) 0.84162(18) 0.4963(4) 0.0683(10) Uani 1 1 d . . . . .
H6 H 0.7543 0.8598 0.5215 0.082 Uiso 1 1 calc R U . . .
C7 C 0.77315(19) 0.84255(18) 0.3963(4) 0.0668(10) Uani 1 1 d . . . . .
C8 C 0.80678(19) 0.81358(18) 0.3578(4) 0.0672(10) Uani 1 1 d . . . . .
H8 H 0.8029 0.8133 0.2916 0.081 Uiso 1 1 calc R U . . .
C9 C 0.84705(19) 0.78439(17) 0.4193(4) 0.0649(9) Uani 1 1 d . . . . .
C10 C 0.8531(2) 0.78623(18) 0.5183(4) 0.0694(10) Uani 1 1 d . . . . .
H10 H 0.8811 0.7684 0.5589 0.083 Uiso 1 1 calc R U . . .
C11 C 0.72882(19) 0.87251(18) 0.3348(4) 0.0660(10) Uani 1 1 d . . . . .
C12 C 0.7215(2) 0.89046(17) 0.2416(4) 0.0669(10) Uani 1 1 d . . . . .
C13 C 0.6409(2) 0.9339(2) 0.1316(4) 0.0740(11) Uani 1 1 d . . . . .
H13A H 0.6643 0.9540 0.1036 0.089 Uiso 1 1 calc R U . . .
H13B H 0.6122 0.9546 0.1432 0.089 Uiso 1 1 calc R U . . .
C14 C 0.6159(2) 0.8939(2) 0.0621(4) 0.0756(12) Uani 1 1 d . . . . .
H14A H 0.5960 0.9078 0.0009 0.091 Uiso 1 1 calc R U . . .
H14B H 0.6443 0.8727 0.0509 0.091 Uiso 1 1 calc R U . . .
C15 C 0.56354(18) 0.8221(2) 0.0641(4) 0.0686(10) Uani 1 1 d . . . . .
C16 C 0.5355(2) 0.7928(2) 0.1155(4) 0.0740(11) Uani 1 1 d . . . . .
H16 H 0.5292 0.8042 0.1726 0.089 Uiso 1 1 calc R U . . .
C17 C 0.5173(2) 0.7471(2) 0.0812(4) 0.0715(10) Uani 1 1 d . . . . .
H17 H 0.4990 0.7277 0.1159 0.086 Uiso 1 1 calc R U . . .
C18 C 0.52577(18) 0.72994(18) -0.0036(4) 0.0676(10) Uani 1 1 d . . . . .
C19 C 0.5528(2) 0.7590(2) -0.0565(4) 0.0729(11) Uani 1 1 d . . . . .
H19 H 0.5583 0.7477 -0.1142 0.087 Uiso 1 1 calc R U . . .
C20 C 0.5714(2) 0.8052(2) -0.0216(4) 0.0735(11) Uani 1 1 d . . . . .
H20 H 0.5893 0.8248 -0.0565 0.088 Uiso 1 1 calc R U . . .
C21 C 0.5134(2) 0.6675(2) -0.1231(5) 0.0752(12) Uani 1 1 d . . . . .
H21A H 0.5518 0.6662 -0.1214 0.090 Uiso 1 1 calc R U . . .
H21B H 0.4951 0.6894 -0.1744 0.090 Uiso 1 1 calc R U . . .
C22 C 0.4886(2) 0.6174(2) -0.1395(4) 0.0698(10) Uani 1 1 d . . . . .
C23 C 0.4325(2) 0.6108(2) -0.1816(5) 0.0761(12) Uani 1 1 d . . . . .
H23 H 0.4100 0.6376 -0.2018 0.091 Uiso 1 1 calc R U . . .
C24 C 0.4115(2) 0.5649(2) -0.1925(4) 0.0754(12) Uani 1 1 d . . . . .
H24 H 0.3743 0.5600 -0.2192 0.090 Uiso 1 1 calc R U . . .
C25 C 0.44654(19) 0.5249(2) -0.1628(3) 0.0662(9) Uani 1 1 d . . . . .
C26 C 0.50216(18) 0.53475(17) -0.1247(3) 0.0616(8) Uani 1 1 d . . . . .
C27 C 0.53968(17) 0.49438(17) -0.0944(3) 0.0596(8) Uani 1 1 d . . . . .
C28 C 0.51890(19) 0.44660(18) -0.0990(3) 0.0636(9) Uani 1 1 d . . . . .
C29 C 0.4616(2) 0.4387(2) -0.1391(4) 0.0703(10) Uani 1 1 d . . . . .
H29 H 0.4482 0.4070 -0.1436 0.084 Uiso 1 1 calc R U . . .
C30 C 0.42699(19) 0.4755(2) -0.1702(4) 0.0718(11) Uani 1 1 d . . . . .
H30 H 0.3901 0.4691 -0.1968 0.086 Uiso 1 1 calc R U . . .
C31 C 0.5554(2) 0.40857(19) -0.0639(4) 0.0734(11) Uani 1 1 d . . . . .
H31 H 0.5431 0.3765 -0.0653 0.088 Uiso 1 1 calc R U . . .
C32 C 0.6094(2) 0.4194(2) -0.0277(5) 0.0766(12) Uani 1 1 d . . . . .
H32 H 0.6342 0.3948 -0.0025 0.092 Uiso 1 1 calc R U . . .
C33 C 0.62725(18) 0.46777(19) -0.0284(4) 0.0685(10) Uani 1 1 d . . . . .
C34 C 0.68681(19) 0.4808(2) 0.0082(4) 0.0703(10) Uani 1 1 d . . . . .
H34A H 0.7095 0.4545 -0.0046 0.084 Uiso 1 1 calc R U . . .
H34B H 0.6949 0.5101 -0.0232 0.084 Uiso 1 1 calc R U . . .
C35 C 0.74461(19) 0.51138(18) 0.1551(4) 0.0683(10) Uani 1 1 d . . . . .
C36 C 0.7864(2) 0.5216(2) 0.1130(5) 0.0765(12) Uani 1 1 d . . . . .
H36 H 0.7838 0.5119 0.0500 0.092 Uiso 1 1 calc R U . . .
C37 C 0.8328(2) 0.5468(3) 0.1659(5) 0.0826(14) Uani 1 1 d . . . . .
H37 H 0.8613 0.5531 0.1380 0.099 Uiso 1 1 calc R U . . .
C38 C 0.8366(2) 0.5622(2) 0.2581(5) 0.0749(12) Uani 1 1 d . . . . .
C39 C 0.7948(2) 0.5505(2) 0.3012(4) 0.0723(10) Uani 1 1 d . . . . .
H39 H 0.7977 0.5599 0.3645 0.087 Uiso 1 1 calc R U . . .
C40 C 0.7498(2) 0.5254(2) 0.2511(4) 0.0720(11) Uani 1 1 d . . . . .
H40 H 0.7225 0.5175 0.2808 0.086 Uiso 1 1 calc R U . . .
C41 C 0.9198(2) 0.6073(3) 0.2712(5) 0.0875(18) Uani 1 1 d . . . . .
H41A H 0.9028 0.6238 0.2110 0.105 Uiso 1 1 calc R U . . .
H41B H 0.9424 0.5810 0.2583 0.105 Uiso 1 1 calc R U . . .
C42 C 0.9538(2) 0.6430(3) 0.3440(5) 0.0825(14) Uani 1 1 d . . . . .
H42A H 0.9626 0.6283 0.4076 0.099 Uiso 1 1 calc R U . . .
H42B H 0.9878 0.6495 0.3274 0.099 Uiso 1 1 calc R U . . .
C43 C 0.89679(17) 0.70396(19) 0.4084(3) 0.0645(9) Uani 1 1 d . . . . .
C44 C 0.88042(18) 0.7503(2) 0.3791(4) 0.0678(10) Uani 1 1 d . . . . .
C45 C 0.8501(3) 0.8797(3) 0.9643(5) 0.0883(16) Uani 1 1 d . . . . .
H45A H 0.8553 0.9058 0.9231 0.132 Uiso 1 1 calc R U . . .
H45B H 0.8147 0.8654 0.9388 0.132 Uiso 1 1 calc R U . . .
H45C H 0.8777 0.8553 0.9676 0.132 Uiso 1 1 calc R U . . .
I1 I 0.77266(2) 0.89269(2) 0.15054(2) 0.06777(16) Uani 1 1 d . . . . .
I2 I 0.87417(2) 0.66082(2) 0.50982(2) 0.06882(16) Uani 1 1 d . . . . .
N1 N 0.68469(19) 0.88631(18) 0.3653(4) 0.0737(10) Uani 1 1 d . . . . .
N2 N 0.65062(19) 0.91065(17) 0.2969(4) 0.0752(10) Uani 1 1 d . . . . .
N3 N 0.67260(17) 0.91377(16) 0.2223(3) 0.0691(9) Uani 1 1 d . . . . .
N4 N 0.52331(15) 0.58074(15) -0.1131(3) 0.0631(8) Uani 1 1 d . . . . .
N5 N 0.59348(15) 0.50448(14) -0.0614(3) 0.0616(7) Uani 1 1 d . . . . .
N6 N 0.92539(16) 0.68857(18) 0.3466(3) 0.0706(9) Uani 1 1 d . . . . .
N7 N 0.9273(2) 0.7236(2) 0.2826(4) 0.0824(12) Uani 1 1 d . . . . .
N8 N 0.8996(2) 0.7612(2) 0.3008(4) 0.0781(11) Uani 1 1 d . . . . .
O1 O 0.58005(16) 0.86705(15) 0.1034(3) 0.0774(8) Uani 1 1 d . . . . .
O2 O 0.50648(15) 0.68383(13) -0.0319(3) 0.0722(8) Uani 1 1 d . . . . .
O3 O 0.69687(14) 0.48864(15) 0.1107(3) 0.0746(8) Uani 1 1 d . . . . .
O4 O 0.87906(17) 0.58888(19) 0.3150(3) 0.0851(11) Uani 1 1 d . . . . .
O5 O 0.85390(19) 0.89780(19) 1.0562(4) 0.0883(12) Uani 1 1 d . . . . .
H5 H 0.8844 0.9094 1.0785 0.132 Uiso 1 1 calc R U . . .
O6 O 0.5000 0.0000 0.0000 0.159(7) Uani 0.8 2 d S . P . .
O7 O 0.5277(6) 0.9601(5) 0.8927(10) 0.157(4) Uani 0.8 1 d . U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.537(10) . ?
C2 C3 1.465(12) . ?
C2 C4 1.537(12) . ?
C2 C5 1.542(7) . ?
C5 C10 1.381(8) . ?
C5 C6 1.403(8) . ?
C6 C7 1.408(8) . ?
C7 C8 1.383(8) . ?
C7 C11 1.483(7) . ?
C8 C9 1.411(7) . ?
C9 C10 1.390(7) . ?
C9 C44 1.477(7) . ?
C11 N1 1.358(7) . ?
C11 C12 1.393(7) . ?
C12 N3 1.358(7) . ?
C12 I1 2.071(5) . ?
C13 N3 1.448(7) . ?
C13 C14 1.507(8) . ?
C14 O1 1.416(6) . ?
C15 O1 1.375(7) . ?
C15 C20 1.377(9) . ?
C15 C16 1.404(7) . ?
C16 C17 1.381(8) . ?
C17 C18 1.375(8) . ?
C18 O2 1.378(6) . ?
C18 C19 1.398(7) . ?
C19 C20 1.399(8) . ?
C21 O2 1.438(7) . ?
C21 C22 1.504(8) . ?
C22 N4 1.324(7) . ?
C22 C23 1.403(8) . ?
C23 C24 1.361(9) . ?
C24 C25 1.405(8) . ?
C25 C26 1.400(6) . ?
C25 C30 1.438(8) . ?
C26 N4 1.363(6) . ?
C26 C27 1.450(6) . ?
C27 N5 1.351(6) . ?
C27 C28 1.407(7) . ?
C28 C31 1.397(7) . ?
C28 C29 1.432(7) . ?
C29 C30 1.335(8) . ?
C31 C32 1.365(8) . ?
C32 C33 1.402(8) . ?
C33 N5 1.326(6) . ?
C33 C34 1.507(6) . ?
C34 O3 1.443(7) . ?
C35 O3 1.363(6) . ?
C35 C36 1.380(8) . ?
C35 C40 1.404(8) . ?
C36 C37 1.404(8) . ?
C37 C38 1.370(9) . ?
C38 O4 1.378(7) . ?
C38 C39 1.397(8) . ?
C39 C40 1.366(8) . ?
C41 O4 1.435(8) . ?
C41 C42 1.524(8) . ?
C42 N6 1.447(8) . ?
C43 N6 1.353(6) . ?
C43 C44 1.368(7) . ?
C43 I2 2.071(5) . ?
C44 N8 1.370(7) . ?
C45 O5 1.389(8) . ?
N1 N2 1.308(7) . ?
N2 N3 1.335(7) . ?
N6 N7 1.340(8) . ?
N7 N8 1.312(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 C1 106.9(10) . . ?
C3 C2 C4 114.5(12) . . ?
C1 C2 C4 105.3(7) . . ?
C3 C2 C5 112.3(6) . . ?
C1 C2 C5 109.0(6) . . ?
C4 C2 C5 108.5(5) . . ?
C10 C5 C6 118.1(5) . . ?
C10 C5 C2 120.0(5) . . ?
C6 C5 C2 121.9(5) . . ?
C5 C6 C7 120.8(5) . . ?
C8 C7 C6 119.8(5) . . ?
C8 C7 C11 122.1(5) . . ?
C6 C7 C11 118.0(5) . . ?
C7 C8 C9 119.8(5) . . ?
C10 C9 C8 119.2(5) . . ?
C10 C9 C44 120.2(5) . . ?
C8 C9 C44 120.6(5) . . ?
C5 C10 C9 122.2(5) . . ?
N1 C11 C12 107.3(5) . . ?
N1 C11 C7 121.6(5) . . ?
C12 C11 C7 131.1(5) . . ?
N3 C12 C11 104.3(5) . . ?
N3 C12 I1 123.2(4) . . ?
C11 C12 I1 132.1(4) . . ?
N3 C13 C14 110.8(4) . . ?
O1 C14 C13 107.8(5) . . ?
O1 C15 C20 124.6(5) . . ?
O1 C15 C16 115.9(5) . . ?
C20 C15 C16 119.4(5) . . ?
C17 C16 C15 120.0(5) . . ?
C18 C17 C16 120.7(5) . . ?
C17 C18 O2 116.7(4) . . ?
C17 C18 C19 120.0(5) . . ?
O2 C18 C19 123.3(5) . . ?
C18 C19 C20 119.3(5) . . ?
C15 C20 C19 120.6(5) . . ?
O2 C21 C22 106.3(4) . . ?
N4 C22 C23 123.3(5) . . ?
N4 C22 C21 115.3(5) . . ?
C23 C22 C21 121.3(5) . . ?
C24 C23 C22 119.4(5) . . ?
C23 C24 C25 119.2(5) . . ?
C26 C25 C24 117.5(5) . . ?
C26 C25 C30 120.2(5) . . ?
C24 C25 C30 122.2(5) . . ?
N4 C26 C25 123.4(4) . . ?
N4 C26 C27 117.6(4) . . ?
C25 C26 C27 119.0(4) . . ?
N5 C27 C28 122.6(4) . . ?
N5 C27 C26 118.2(4) . . ?
C28 C27 C26 119.2(4) . . ?
C31 C28 C27 118.2(4) . . ?
C31 C28 C29 122.6(5) . . ?
C27 C28 C29 119.2(5) . . ?
C30 C29 C28 122.0(5) . . ?
C29 C30 C25 120.2(4) . . ?
C32 C31 C28 118.6(5) . . ?
C31 C32 C33 119.8(5) . . ?
N5 C33 C32 122.7(4) . . ?
N5 C33 C34 116.1(4) . . ?
C32 C33 C34 121.2(5) . . ?
O3 C34 C33 106.5(4) . . ?
O3 C35 C36 125.3(5) . . ?
O3 C35 C40 115.4(5) . . ?
C36 C35 C40 119.3(5) . . ?
C35 C36 C37 119.6(5) . . ?
C38 C37 C36 120.8(5) . . ?
C37 C38 O4 125.6(5) . . ?
C37 C38 C39 119.2(5) . . ?
O4 C38 C39 115.2(5) . . ?
C40 C39 C38 120.6(5) . . ?
C39 C40 C35 120.3(5) . . ?
O4 C41 C42 105.6(5) . . ?
N6 C42 C41 112.1(5) . . ?
N6 C43 C44 105.0(4) . . ?
N6 C43 I2 125.4(4) . . ?
C44 C43 I2 129.0(3) . . ?
C43 C44 N8 108.1(5) . . ?
C43 C44 C9 128.7(4) . . ?
N8 C44 C9 123.1(5) . . ?
N2 N1 C11 109.8(5) . . ?
N1 N2 N3 107.6(4) . . ?
N2 N3 C12 110.9(4) . . ?
N2 N3 C13 119.7(4) . . ?
C12 N3 C13 128.7(5) . . ?
C22 N4 C26 117.1(4) . . ?
C33 N5 C27 117.9(4) . . ?
N7 N6 C43 110.5(5) . . ?
N7 N6 C42 119.5(5) . . ?
C43 N6 C42 130.0(5) . . ?
N8 N7 N6 107.9(4) . . ?
N7 N8 C44 108.5(5) . . ?
C15 O1 C14 117.0(5) . . ?
C18 O2 C21 115.9(4) . . ?
C35 O3 C34 116.4(4) . . ?
C38 O4 C41 117.9(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5 N4 0.82 2.28 3.064(6) 160.4 7_666
O5 H5 N5 0.82 2.45 2.985(6) 123.4 7_666

_refine_diff_density_max         3.051
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.279

