# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

####################################################################### 
# 
# 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_test
_database_code_depnum_ccdc_archive 'CCDC 1046596'
_audit_update_record             
;
2015-01-31 deposited with the CCDC.
2015-03-27 downloaded from the CCDC.
;
_audit_creation_date             2015-01-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4975)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        diiodide
_chemical_formula_moiety         'C10 H7 I2 N O'
_chemical_formula_sum            'C17 H0 I2 N3 O6'
_chemical_formula_weight         596.00
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.5881(2)
_cell_length_b                   18.9850(6)
_cell_length_c                   10.6706(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.113(3)
_cell_angle_gamma                90
_cell_volume                     1129.13(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2923
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      63.733
_cell_measurement_theta_min      4.659
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    44.378
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    3.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1108
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1088
_diffrn_reflns_av_unetI/netI     0.1102
_diffrn_reflns_Laue_measured_fraction_full 0.884
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5016
_diffrn_reflns_point_group_measured_fraction_full 0.884
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         63.733
_diffrn_reflns_theta_min         4.658
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.884
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1481
_reflns_number_total             1807
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         6.024
_refine_diff_density_min         -2.001
_refine_diff_density_rms         0.579
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.212
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1807
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1236
_refine_ls_R_factor_gt           0.1113
_refine_ls_restrained_S_all      1.212
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2803
_refine_ls_wR_factor_ref         0.2931
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
I2 I 0.4419(2) 0.59907(5) 0.47933(11) 0.0499(6) Uani 1 1 d . . . . .
O5 O 0.737(2) 0.7925(5) 0.6252(11) 0.038(2) Uani 1 1 d . . . . .
N1 N 0.996(2) 0.7908(8) 0.4732(13) 0.039(3) Uani 1 1 d . . . . .
C1 C 1.002(3) 0.8907(8) 0.6196(17) 0.036(3) Uani 1 1 d . . . . .
C2 C 0.879(3) 0.9265(8) 0.7107(18) 0.047(4) Uani 1 1 d . . . . .
H2 H 0.7435 0.9057 0.7409 0.056 Uiso 1 1 calc R . . . .
C3 C 1.284(4) 0.9882(10) 0.622(3) 0.066(6) Uani 1 1 d . . . . .
H3 H 1.4197 1.0091 0.5932 0.080 Uiso 1 1 calc R . . . .
C4 C 1.208(3) 0.9227(10) 0.577(2) 0.057(5) Uani 1 1 d . . . . .
H4 H 1.2941 0.8997 0.5180 0.068 Uiso 1 1 calc R . . . .
C6 C 0.919(2) 0.8235(8) 0.5653(15) 0.032(3) Uani 1 1 d . . . . .
C7 C 0.952(4) 0.9912(10) 0.756(2) 0.058(5) Uani 1 1 d . . . . .
H7 H 0.8653 1.0136 0.8163 0.070 Uiso 1 1 calc R . . . .
C8 C 0.855(3) 0.7269(8) 0.4600(16) 0.039(3) Uani 1 1 d . . . . .
H8A H 0.9576 0.6858 0.4713 0.047 Uiso 1 1 calc R . . . .
H8B H 0.7700 0.7246 0.3777 0.047 Uiso 1 1 calc R . . . .
C9 C 0.684(3) 0.7309(7) 0.5606(16) 0.036(3) Uani 1 1 d . . . . .
C5 C 0.516(3) 0.6862(7) 0.5941(14) 0.033(3) Uani 1 1 d . . . . .
C10 C 1.153(4) 1.0233(9) 0.7140(19) 0.053(5) Uani 1 1 d . . . . .
H10 H 1.2024 1.0672 0.7447 0.063 Uiso 1 1 calc R . . . .
I1 I 0.31628(16) 0.69768(4) 0.75003(9) 0.0373(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I2 C5 2.082(14) . ?
O5 C6 1.371(18) . ?
O5 C9 1.378(18) . ?
N1 C6 1.26(2) . ?
N1 C8 1.45(2) . ?
C1 C2 1.41(2) . ?
C1 C4 1.40(2) . ?
C1 C6 1.46(2) . ?
C2 C7 1.37(3) . ?
C3 C4 1.39(3) . ?
C3 C10 1.43(3) . ?
C7 C10 1.38(3) . ?
C8 C9 1.49(2) . ?
C9 C5 1.33(2) . ?
C5 I1 2.082(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O5 C9 105.7(12) . . ?
C6 N1 C8 106.0(13) . . ?
C2 C1 C6 122.5(14) . . ?
C4 C1 C2 117.9(15) . . ?
C4 C1 C6 119.6(15) . . ?
C7 C2 C1 122.0(15) . . ?
C4 C3 C10 119.8(18) . . ?
C3 C4 C1 120.8(18) . . ?
O5 C6 C1 114.6(13) . . ?
N1 C6 O5 117.2(14) . . ?
N1 C6 C1 128.3(14) . . ?
C2 C7 C10 120.3(16) . . ?
N1 C8 C9 105.0(13) . . ?
O5 C9 C8 106.2(12) . . ?
C5 C9 O5 122.4(14) . . ?
C5 C9 C8 131.4(14) . . ?
C9 C5 I2 117.6(11) . . ?
C9 C5 I1 125.2(11) . . ?
I1 C5 I2 117.2(7) . . ?
C7 C10 C3 119.2(16) . . ?

_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_p
_database_code_depnum_ccdc_archive 'CCDC 1046597'
_audit_update_record             
;
2015-01-31 deposited with the CCDC.
2015-03-27 downloaded from the CCDC.
;
_audit_creation_date             2015-01-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_chemical_name_common            ?
_chemical_name_systematic        zhangshuotrienes
_chemical_formula_moiety         'C23 H25 N O5'
_chemical_formula_sum            'C23 H25 N O5'
_chemical_formula_weight         395.44
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   9.2215(6)
_cell_length_b                   10.9612(7)
_cell_length_c                   11.6484(7)
_cell_angle_alpha                87.764(2)
_cell_angle_beta                 69.092(3)
_cell_angle_gamma                73.409(3)
_cell_volume                     1051.48(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7009
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      63.77
_cell_measurement_theta_min      4.07
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             420
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8884
_diffrn_reflns_theta_full        63.77
_diffrn_reflns_theta_max         63.77
_diffrn_reflns_theta_min         4.07
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.933
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                3074
_reflns_number_total             3233
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0095(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0539
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          1.430
_refine_ls_shift/su_mean         0.026
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0765P)²+0.4630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1496
_refine_ls_wR_factor_ref         0.1513
_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. 
;
_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 Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C16(H16), C17(H17), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C -0.4435(3) 0.4463(2) 0.2407(2) 0.0642(6) Uani 1 d . . .
H1 H -0.5445 0.4937 0.2948 0.077 Uiso 1 calc . . R
C2 C -0.3483(3) 0.3471(2) 0.2812(2) 0.0679(7) Uani 1 d . . .
H2 H -0.3848 0.3278 0.3631 0.081 Uiso 1 calc . . R
C3 C -0.1986(3) 0.2758(2) 0.2012(2) 0.0577(6) Uani 1 d . . .
H3 H -0.1352 0.2085 0.2293 0.069 Uiso 1 calc . . R
C4 C -0.1424(2) 0.30448(18) 0.07881(18) 0.0469(5) Uani 1 d . . .
C5 C -0.2390(3) 0.4056(2) 0.0388(2) 0.0602(6) Uani 1 d . . .
H5 H -0.2025 0.4265 -0.0427 0.072 Uiso 1 calc . . R
C6 C -0.3887(3) 0.4750(2) 0.1197(2) 0.0661(6) Uani 1 d . . .
H6 H -0.4533 0.5420 0.0921 0.079 Uiso 1 calc . . R
C7 C 0.0131(2) 0.22743(18) -0.00916(18) 0.0455(5) Uani 1 d . . .
C8 C 0.2320(2) 0.05980(18) -0.05858(17) 0.0430(5) Uani 1 d . . .
C9 C 0.2335(2) 0.13784(17) -0.17011(17) 0.0421(5) Uani 1 d . . .
C10 C 0.3782(3) 0.19310(19) -0.21821(19) 0.0492(5) Uani 1 d . . .
H10A H 0.3738 0.2486 -0.1534 0.059 Uiso 1 calc . . R
H10B H 0.4782 0.1238 -0.2388 0.059 Uiso 1 calc . . R
C11 C 0.3803(3) 0.2680(2) -0.3309(2) 0.0544(5) Uani 1 d . . .
H11A H 0.2878 0.3439 -0.3079 0.065 Uiso 1 calc . . R
H11B H 0.4780 0.2950 -0.3613 0.065 Uiso 1 calc . . R
C12 C 0.3747(3) 0.1891(2) -0.4323(2) 0.0619(6) Uani 1 d . . .
H12A H 0.4725 0.1176 -0.4610 0.074 Uiso 1 calc . . R
H12B H 0.3709 0.2409 -0.5011 0.074 Uiso 1 calc . . R
C13 C 0.2273(3) 0.1396(2) -0.38662(19) 0.0547(5) Uani 1 d . . .
H13A H 0.1296 0.2112 -0.3654 0.066 Uiso 1 calc . . R
H13B H 0.2293 0.0864 -0.4520 0.066 Uiso 1 calc . . R
C14 C 0.2234(2) 0.06302(18) -0.27493(18) 0.0459(5) Uani 1 d . . .
H14A H 0.3137 -0.0145 -0.2992 0.055 Uiso 1 calc . . R
H14B H 0.1239 0.0386 -0.2448 0.055 Uiso 1 calc . . R
C15 C 0.3316(2) -0.05049(18) -0.04092(18) 0.0456(5) Uani 1 d . . .
C16 C 0.4817(2) -0.11695(18) -0.13930(19) 0.0468(5) Uani 1 d . . .
H16 H 0.5014 -0.0844 -0.2165 0.056 Uiso 1 calc . . R
C17 C 0.5929(3) -0.21956(19) -0.1287(2) 0.0519(5) Uani 1 d . . .
H17 H 0.5785 -0.2520 -0.0517 0.062 Uiso 1 calc . . R
C18 C 0.7368(3) -0.2834(2) -0.2332(2) 0.0546(5) Uani 1 d . . .
C19 C 0.9591(4) -0.4697(3) -0.2985(3) 0.1043(12) Uani 1 d . . .
H19A H 0.9302 -0.4844 -0.3671 0.156 Uiso 1 calc . . GR
H19B H 0.9997 -0.5499 -0.2680 0.156 Uiso 1 calc . . GR
H19C H 1.0414 -0.4265 -0.3246 0.156 Uiso 1 calc . . GR
C20 C 0.2927(3) -0.1144(2) 0.0741(2) 0.0531(5) Uani 1 d . . .
H20 H 0.3258 -0.2030 0.0631 0.064 Uiso 1 calc . . R
C21 C 0.2224(3) -0.0719(2) 0.1861(2) 0.0559(6) Uani 1 d . . .
H21 H 0.1809 0.0157 0.2056 0.067 Uiso 1 calc . . R
C22 C 0.2060(2) -0.1613(2) 0.2869(2) 0.0554(5) Uani 1 d . . .
C23 C 0.1279(4) -0.1753(3) 0.4986(2) 0.0842(8) Uani 1 d . . .
H23A H 0.2291 -0.2381 0.4889 0.126 Uiso 1 calc . . GR
H23B H 0.0470 -0.2171 0.5060 0.126 Uiso 1 calc . . GR
H23C H 0.0944 -0.1206 0.5715 0.126 Uiso 1 calc . . GR
N1 N 0.0824(2) 0.24380(15) -0.12079(15) 0.0461(4) Uani 1 d . . .
O1 O 0.8189(2) -0.39247(16) -0.20273(18) 0.0850(6) Uani 1 d . . .
O2 O 0.7785(2) -0.2461(2) -0.33346(18) 0.0947(7) Uani 1 d . . .
O3 O 0.09231(17) 0.12004(13) 0.03780(12) 0.0503(4) Uani 1 d . . .
O4 O 0.2430(2) -0.27476(19) 0.27227(16) 0.0790(5) Uani 1 d . . .
O5 O 0.1476(2) -0.10114(17) 0.39411(16) 0.0768(5) Uani 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.373(4) . ?
C1 C6 1.374(3) . ?
C2 C3 1.381(3) . ?
C3 C4 1.389(3) . ?
C4 C5 1.390(3) . ?
C4 C7 1.465(3) . ?
C5 C6 1.379(3) . ?
C7 N1 1.259(3) . ?
C7 O3 1.401(2) . ?
C8 C9 1.526(3) . ?
C8 C15 1.352(3) . ?
C8 O3 1.377(2) . ?
C9 C10 1.537(3) . ?
C9 C14 1.541(3) . ?
C9 N1 1.475(2) . ?
C10 C11 1.518(3) . ?
C11 C12 1.514(3) . ?
C12 C13 1.519(3) . ?
C13 C14 1.516(3) . ?
C15 C16 1.455(3) . ?
C15 C20 1.464(3) . ?
C16 C17 1.324(3) . ?
C17 C18 1.455(3) . ?
C18 O1 1.331(3) . ?
C18 O2 1.188(3) . ?
C19 O1 1.433(3) . ?
C20 C21 1.269(3) . ?
C21 C22 1.494(3) . ?
C22 O4 1.194(3) . ?
C22 O5 1.290(3) . ?
C23 O5 1.423(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.6(2) . . ?
C1 C2 C3 120.5(2) . . ?
C2 C3 C4 120.1(2) . . ?
C3 C4 C5 119.0(2) . . ?
C3 C4 C7 121.29(18) . . ?
C5 C4 C7 119.69(19) . . ?
C6 C5 C4 120.1(2) . . ?
C1 C6 C5 120.7(2) . . ?
N1 C7 C4 128.68(18) . . ?
N1 C7 O3 116.39(17) . . ?
O3 C7 C4 114.92(17) . . ?
C15 C8 C9 133.73(18) . . ?
C15 C8 O3 119.15(17) . . ?
O3 C8 C9 107.07(15) . . ?
C8 C9 C10 113.14(15) . . ?
C8 C9 C14 112.39(15) . . ?
C10 C9 C14 110.73(16) . . ?
N1 C9 C8 102.87(15) . . ?
N1 C9 C10 108.94(15) . . ?
N1 C9 C14 108.33(15) . . ?
C11 C10 C9 112.59(16) . . ?
C12 C11 C10 111.55(17) . . ?
C11 C12 C13 111.02(18) . . ?
C14 C13 C12 111.52(17) . . ?
C13 C14 C9 112.52(16) . . ?
C8 C15 C16 121.28(18) . . ?
C8 C15 C20 122.99(19) . . ?
C16 C15 C20 115.64(17) . . ?
C17 C16 C15 125.85(19) . . ?
C16 C17 C18 122.3(2) . . ?
O1 C18 C17 110.92(19) . . ?
O2 C18 C17 126.0(2) . . ?
O2 C18 O1 123.1(2) . . ?
C21 C20 C15 132.2(2) . . ?
C20 C21 C22 120.5(2) . . ?
O4 C22 C21 125.2(2) . . ?
O4 C22 O5 123.1(2) . . ?
O5 C22 C21 111.7(2) . . ?
C7 N1 C9 107.73(15) . . ?
C18 O1 C19 117.3(2) . . ?
C8 O3 C7 105.94(14) . . ?
C22 O5 C23 117.6(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'

