# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_cqn1
_audit_block_doi                 10.5517/ccdc.csd.cc1prj43
_database_code_depnum_ccdc_archive 'CCDC 1571735'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C9TC01199D 2019
_audit_update_record             
;
2017-08-31 deposited with the CCDC.	2019-07-10 downloaded from the CCDC.
;
_audit_creation_date             2017-07-30
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        1-2y
_chemical_formula_moiety         'C20 H21 N3 O3'
_chemical_formula_sum            'C20 H21 N3 O3'
_chemical_formula_weight         351.40
_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'
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           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                   10.118(2)
_cell_length_b                   9.1993(18)
_cell_length_c                   20.098(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.49(3)
_cell_angle_gamma                90
_cell_volume                     1839.4(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2866
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.328
_cell_measurement_theta_min      2.869
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            17394
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         3.016
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2866
_reflns_number_total             4194
_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, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.057
_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)+(0.0675P)²+0.0886P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1289
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C13(H13), C15(H15), C16(H16), C17(H17), C19(H19), C22(H22)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.74764(14) 1.01520(15) 0.16555(6) 0.0494(3) Uani 1 1 d . . . . .
O3 O 0.87394(13) 1.16811(13) 0.26953(5) 0.0650(4) Uani 1 1 d . . . . .
C3 C 0.78548(15) 1.04922(17) 0.42834(7) 0.0466(4) Uani 1 1 d . . . . .
H3 H 0.7202 0.9800 0.4128 0.056 Uiso 1 1 calc R . . . .
C4 C 0.70231(14) 0.93890(16) 0.21524(6) 0.0417(3) Uani 1 1 d . . . . .
C5 C 0.70067(14) 0.95839(16) 0.10196(6) 0.0420(3) Uani 1 1 d . . . . .
C6 C 0.81984(15) 1.09163(16) 0.30792(7) 0.0446(3) Uani 1 1 d . . . . .
C7 C 0.91456(14) 1.17902(16) 0.52260(7) 0.0435(3) Uani 1 1 d . . . . .
C8 C 0.84793(14) 1.12138(15) 0.38170(6) 0.0406(3) Uani 1 1 d . . . . .
C9 C 0.73205(15) 0.97262(16) 0.28192(7) 0.0443(3) Uani 1 1 d . . . . .
H9 H 0.6944 0.9169 0.3123 0.053 Uiso 1 1 calc R . . . .
C10 C 0.62317(14) 0.83599(15) 0.10831(6) 0.0403(3) Uani 1 1 d . . . . .
N1 N 0.53023(14) 0.73153(16) -0.07170(6) 0.0521(3) Uani 1 1 d . . . . .
N3 N 0.94576(14) 1.20769(15) 0.59092(6) 0.0541(4) Uani 1 1 d . . . . .
C13 C 0.56653(15) 0.75872(16) 0.05154(6) 0.0437(3) Uani 1 1 d . . . . .
H13 H 0.5152 0.6759 0.0546 0.052 Uiso 1 1 calc R . . . .
C14 C 0.58953(14) 0.81014(16) -0.01080(6) 0.0418(3) Uani 1 1 d . . . . .
C15 C 0.97707(16) 1.25355(17) 0.47592(7) 0.0504(4) Uani 1 1 d . . . . .
H15 H 1.0421 1.3232 0.4914 0.060 Uiso 1 1 calc R . . . .
C16 C 0.81668(16) 1.07652(17) 0.49653(7) 0.0483(4) Uani 1 1 d . . . . .
H16 H 0.7720 1.0260 0.5259 0.058 Uiso 1 1 calc R . . . .
C17 C 0.66406(16) 0.93252(18) -0.01700(7) 0.0488(4) Uani 1 1 d . . . . .
H17 H 0.6759 0.9635 -0.0596 0.059 Uiso 1 1 calc R . . . .
C18 C 0.61554(15) 0.81340(16) 0.18250(6) 0.0444(3) Uani 1 1 d . . . . .
C19 C 0.94404(16) 1.22564(17) 0.40775(7) 0.0484(4) Uani 1 1 d . . . . .
H19 H 0.9868 1.2776 0.3781 0.058 Uiso 1 1 calc R . . . .
O1 O 0.46543(14) 0.62107(16) -0.06644(5) 0.0739(4) Uani 1 1 d . . . . .
O2 O 0.54971(16) 0.77689(16) -0.12642(5) 0.0828(4) Uani 1 1 d . . . . .
C22 C 0.72130(16) 1.00942(18) 0.03980(7) 0.0508(4) Uani 1 1 d . . . . .
H22 H 0.7720 1.0926 0.0365 0.061 Uiso 1 1 calc R . . . .
C23 C 0.88718(19) 1.1207(2) 0.63836(7) 0.0612(5) Uani 1 1 d . . . . .
H23A H 0.7916 1.1351 0.6304 0.092 Uiso 1 1 calc GR . . . .
H23B H 0.9248 1.1495 0.6838 0.092 Uiso 1 1 calc GR . . . .
H23C H 0.9064 1.0199 0.6323 0.092 Uiso 1 1 calc GR . . . .
C24 C 1.05117(19) 1.3095(2) 0.61731(8) 0.0681(5) Uani 1 1 d . . . . .
H24A H 1.1351 1.2756 0.6072 0.102 Uiso 1 1 calc GR . . . .
H24B H 1.0580 1.3177 0.6654 0.102 Uiso 1 1 calc GR . . . .
H24C H 1.0304 1.4029 0.5968 0.102 Uiso 1 1 calc GR . . . .
C25 C 0.6754(2) 0.66708(18) 0.20873(8) 0.0722(6) Uani 1 1 d . . . . .
H25A H 0.7667 0.6609 0.2018 0.108 Uiso 1 1 calc GR . . . .
H25B H 0.6237 0.5897 0.1847 0.108 Uiso 1 1 calc GR . . . .
H25C H 0.6734 0.6588 0.2561 0.108 Uiso 1 1 calc GR . . . .
C26 C 0.47111(18) 0.8304(2) 0.19436(8) 0.0669(5) Uani 1 1 d . . . . .
H26A H 0.4696 0.8212 0.2418 0.100 Uiso 1 1 calc GR . . . .
H26B H 0.4156 0.7564 0.1699 0.100 Uiso 1 1 calc GR . . . .
H26C H 0.4375 0.9244 0.1789 0.100 Uiso 1 1 calc GR . . . .
H2 H 0.798(2) 1.089(2) 0.1768(9) 0.077(6) Uiso 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
N2 C4 1.3664(18) . ?
N2 C5 1.3824(17) . ?
N2 H2 0.86(2) . ?
O3 C6 1.2424(18) . ?
C3 H3 0.9300 . ?
C3 C8 1.391(2) . ?
C3 C16 1.372(2) . ?
C4 C9 1.3550(18) . ?
C4 C18 1.5252(19) . ?
C5 C10 1.391(2) . ?
C5 C22 1.3856(19) . ?
C6 C8 1.4837(19) . ?
C6 C9 1.446(2) . ?
C7 N3 1.3771(18) . ?
C7 C15 1.402(2) . ?
C7 C16 1.398(2) . ?
C8 C19 1.398(2) . ?
C9 H9 0.9300 . ?
C10 C13 1.3775(18) . ?
C10 C18 1.5214(18) . ?
N1 C14 1.4539(18) . ?
N1 O1 1.2242(19) . ?
N1 O2 1.2254(17) . ?
N3 C23 1.451(2) . ?
N3 C24 1.446(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.3977(19) . ?
C14 C17 1.373(2) . ?
C15 H15 0.9300 . ?
C15 C19 1.374(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C17 C22 1.378(2) . ?
C18 C25 1.530(2) . ?
C18 C26 1.531(2) . ?
C19 H19 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
C4 N2 C5 112.14(12) . . ?
C4 N2 H2 118.6(13) . . ?
C5 N2 H2 129.3(13) . . ?
C8 C3 H3 118.8 . . ?
C16 C3 H3 118.8 . . ?
C16 C3 C8 122.38(14) . . ?
N2 C4 C18 108.48(11) . . ?
C9 C4 N2 124.17(13) . . ?
C9 C4 C18 127.35(13) . . ?
N2 C5 C10 109.02(12) . . ?
N2 C5 C22 128.51(14) . . ?
C22 C5 C10 122.47(13) . . ?
O3 C6 C8 119.36(13) . . ?
O3 C6 C9 121.02(12) . . ?
C9 C6 C8 119.61(13) . . ?
N3 C7 C15 121.59(14) . . ?
N3 C7 C16 121.39(14) . . ?
C16 C7 C15 116.99(12) . . ?
C3 C8 C6 123.90(13) . . ?
C3 C8 C19 116.45(12) . . ?
C19 C8 C6 119.64(13) . . ?
C4 C9 C6 122.81(13) . . ?
C4 C9 H9 118.6 . . ?
C6 C9 H9 118.6 . . ?
C5 C10 C18 109.30(11) . . ?
C13 C10 C5 119.88(12) . . ?
C13 C10 C18 130.82(13) . . ?
O1 N1 C14 119.05(13) . . ?
O1 N1 O2 122.43(13) . . ?
O2 N1 C14 118.50(15) . . ?
C7 N3 C23 120.16(13) . . ?
C7 N3 C24 120.65(14) . . ?
C24 N3 C23 118.58(12) . . ?
C10 C13 H13 121.4 . . ?
C10 C13 C14 117.11(14) . . ?
C14 C13 H13 121.4 . . ?
C13 C14 N1 118.41(14) . . ?
C17 C14 N1 118.73(13) . . ?
C17 C14 C13 122.86(13) . . ?
C7 C15 H15 119.4 . . ?
C19 C15 C7 121.22(14) . . ?
C19 C15 H15 119.4 . . ?
C3 C16 C7 121.07(14) . . ?
C3 C16 H16 119.5 . . ?
C7 C16 H16 119.5 . . ?
C14 C17 H17 120.0 . . ?
C14 C17 C22 120.05(13) . . ?
C22 C17 H17 120.0 . . ?
C4 C18 C25 110.89(13) . . ?
C4 C18 C26 110.25(13) . . ?
C10 C18 C4 101.04(11) . . ?
C10 C18 C25 111.74(13) . . ?
C10 C18 C26 111.03(12) . . ?
C25 C18 C26 111.45(15) . . ?
C8 C19 H19 119.1 . . ?
C15 C19 C8 121.87(14) . . ?
C15 C19 H19 119.1 . . ?
C5 C22 H22 121.2 . . ?
C17 C22 C5 117.61(14) . . ?
C17 C22 H22 121.2 . . ?
N3 C23 H23A 109.5 . . ?
N3 C23 H23B 109.5 . . ?
N3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N3 C24 H24A 109.5 . . ?
N3 C24 H24B 109.5 . . ?
N3 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C18 C25 H25A 109.5 . . ?
C18 C25 H25B 109.5 . . ?
C18 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C18 C26 H26A 109.5 . . ?
C18 C26 H26B 109.5 . . ?
C18 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_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_1
_audit_block_doi                 10.5517/ccdc.csd.cc1pfpg8
_database_code_depnum_ccdc_archive 'CCDC 1562290'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C9TC01199D 2019
_audit_update_record             
;
2017-07-14 deposited with the CCDC.	2019-07-10 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            'C22 H25 I N2 O'
_chemical_formula_weight         460.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.1317(10)
_cell_length_b                   7.4780(4)
_cell_length_c                   13.4306(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.394(2)
_cell_angle_gamma                90
_cell_volume                     2015.96(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2234
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      21.81

_exptl_crystal_description       Block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.601
_shelx_estimated_absorpt_T_min   0.720
_shelx_estimated_absorpt_T_max   0.761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12417
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.014
_diffrn_reflns_theta_max         25.054
_diffrn_reflns_theta_full        25.054
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3542
_reflns_number_gt                2608
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0299P)²+1.4588P] 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         3542
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0869
_refine_ls_wR_factor_gt          0.0777
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.07847(19) 0.2708(5) 0.9178(3) 0.0376(9) Uani 1 1 d . . . . .
C2 C 0.0105(2) 0.2664(6) 0.9227(3) 0.0472(10) Uani 1 1 d . . . . .
H2 H -0.0094 0.1756 0.9572 0.057 Uiso 1 1 calc R U . . .
C3 C -0.0280(2) 0.4011(6) 0.8748(3) 0.0530(11) Uani 1 1 d . . . . .
H3 H -0.0739 0.4015 0.8785 0.064 Uiso 1 1 calc R U . . .
C4 C 0.0015(2) 0.5326(6) 0.8224(3) 0.0530(12) Uani 1 1 d . . . . .
H4 H -0.0251 0.6193 0.7896 0.064 Uiso 1 1 calc R U . . .
C5 C 0.0700(2) 0.5398(5) 0.8171(3) 0.0431(10) Uani 1 1 d . . . . .
H5 H 0.0900 0.6296 0.7820 0.052 Uiso 1 1 calc R U . . .
C6 C 0.10686(19) 0.4072(5) 0.8665(2) 0.0360(9) Uani 1 1 d . . . . .
C7 C 0.13301(19) 0.1475(5) 0.9601(3) 0.0386(9) Uani 1 1 d . . . . .
C8 C 0.1278(2) -0.0386(5) 0.9108(3) 0.0500(11) Uani 1 1 d . . . . .
H8A H 0.1326 -0.0272 0.8405 0.075 Uiso 1 1 calc R U . . .
H8B H 0.0852 -0.0902 0.9209 0.075 Uiso 1 1 calc R U . . .
H8C H 0.1625 -0.1144 0.9402 0.075 Uiso 1 1 calc R U . . .
C9 C 0.1340(2) 0.1332(5) 1.0744(3) 0.0483(10) Uani 1 1 d . . . . .
H9A H 0.1682 0.0510 1.0984 0.072 Uiso 1 1 calc R U . . .
H9B H 0.0916 0.0909 1.0926 0.072 Uiso 1 1 calc R U . . .
H9C H 0.1429 0.2487 1.1036 0.072 Uiso 1 1 calc R U . . .
C10 C 0.19464(18) 0.2404(5) 0.9280(2) 0.0345(9) Uani 1 1 d . . . . .
C11 C 0.25893(19) 0.1789(5) 0.9572(3) 0.0410(9) Uani 1 1 d . . . . .
H11 H 0.2602 0.0765 0.9966 0.049 Uiso 1 1 calc R U . . .
C12 C 0.3198(2) 0.2434(5) 0.9377(3) 0.0423(10) Uani 1 1 d . . . . .
C13 C 0.2783(2) 0.3992(6) 0.7887(3) 0.0529(11) Uani 1 1 d . . . . .
H13A H 0.2608 0.2880 0.7603 0.063 Uiso 1 1 calc R U . . .
H13B H 0.2964 0.4673 0.7356 0.063 Uiso 1 1 calc R U . . .
C14 C 0.2226(2) 0.5034(5) 0.8294(3) 0.0454(10) Uani 1 1 d . . . . .
H14A H 0.2407 0.5875 0.8794 0.054 Uiso 1 1 calc R U . . .
H14B H 0.1990 0.5708 0.7760 0.054 Uiso 1 1 calc R U . . .
C15 C 0.3822(2) 0.2000(5) 0.9965(3) 0.0414(9) Uani 1 1 d . . . . .
C16 C 0.3846(2) 0.0801(6) 1.0754(3) 0.0474(10) Uani 1 1 d . . . . .
H16 H 0.3460 0.0203 1.0899 0.057 Uiso 1 1 calc R U . . .
C17 C 0.4435(2) 0.0477(6) 1.1332(3) 0.0503(11) Uani 1 1 d . . . . .
H17 H 0.4439 -0.0347 1.1851 0.060 Uiso 1 1 calc R U . . .
C18 C 0.5025(2) 0.1373(5) 1.1145(3) 0.0426(9) Uani 1 1 d . . . . .
C19 C 0.4996(2) 0.2537(5) 1.0317(3) 0.0467(10) Uani 1 1 d . . . . .
H19 H 0.5380 0.3124 1.0155 0.056 Uiso 1 1 calc R U . . .
C20 C 0.4415(2) 0.2818(5) 0.9752(3) 0.0472(10) Uani 1 1 d . . . . .
H20 H 0.4415 0.3581 0.9205 0.057 Uiso 1 1 calc R U . . .
C21 C 0.5650(2) -0.0046(7) 1.2572(3) 0.0700(14) Uani 1 1 d . . . . .
H21A H 0.5315 0.0262 1.3014 0.105 Uiso 1 1 calc R U . . .
H21B H 0.6083 0.0061 1.2920 0.105 Uiso 1 1 calc R U . . .
H21C H 0.5583 -0.1255 1.2346 0.105 Uiso 1 1 calc R U . . .
C22 C 0.6210(2) 0.2062(6) 1.1495(3) 0.0579(12) Uani 1 1 d . . . . .
H22A H 0.6338 0.1670 1.0856 0.087 Uiso 1 1 calc R U . . .
H22B H 0.6560 0.1792 1.1999 0.087 Uiso 1 1 calc R U . . .
H22C H 0.6133 0.3328 1.1477 0.087 Uiso 1 1 calc R U . . .
I1 I 0.24014(2) 0.64415(4) 0.11800(2) 0.06844(15) Uani 1 1 d . . . . .
N1 N 0.17683(15) 0.3837(4) 0.8737(2) 0.0351(7) Uani 1 1 d . . . . .
N2 N 0.56037(17) 0.1146(4) 1.1725(2) 0.0496(9) Uani 1 1 d . . . . .
O1 O 0.33093(14) 0.3599(4) 0.8643(2) 0.0559(8) 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
C1 C2 1.375(5) . ?
C1 C6 1.379(5) . ?
C1 C7 1.511(5) . ?
C2 C3 1.397(6) . ?
C3 C4 1.370(6) . ?
C4 C5 1.386(6) . ?
C5 C6 1.379(5) . ?
C6 N1 1.416(5) . ?
C7 C10 1.513(5) . ?
C7 C8 1.541(5) . ?
C7 C9 1.538(5) . ?
C10 N1 1.330(4) . ?
C10 C11 1.401(5) . ?
C11 C12 1.361(5) . ?
C12 O1 1.348(4) . ?
C12 C15 1.468(5) . ?
C13 O1 1.440(5) . ?
C13 C14 1.504(6) . ?
C14 N1 1.444(5) . ?
C15 C20 1.390(5) . ?
C15 C16 1.387(5) . ?
C16 C17 1.389(5) . ?
C17 C18 1.403(6) . ?
C18 N2 1.362(5) . ?
C18 C19 1.409(5) . ?
C19 C20 1.360(5) . ?
C21 N2 1.443(5) . ?
C22 N2 1.454(5) . ?

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(4) . . ?
C2 C1 C7 131.7(4) . . ?
C6 C1 C7 108.8(3) . . ?
C1 C2 C3 118.6(4) . . ?
C4 C3 C2 120.5(4) . . ?
C3 C4 C5 121.7(4) . . ?
C6 C5 C4 116.7(4) . . ?
C1 C6 C5 122.9(4) . . ?
C1 C6 N1 108.8(3) . . ?
C5 C6 N1 128.2(4) . . ?
C1 C7 C10 101.6(3) . . ?
C1 C7 C8 111.5(3) . . ?
C10 C7 C8 108.8(3) . . ?
C1 C7 C9 111.8(3) . . ?
C10 C7 C9 111.6(3) . . ?
C8 C7 C9 111.2(3) . . ?
N1 C10 C11 128.5(4) . . ?
N1 C10 C7 109.5(3) . . ?
C11 C10 C7 122.0(3) . . ?
C12 C11 C10 131.0(4) . . ?
O1 C12 C11 124.9(4) . . ?
O1 C12 C15 110.7(4) . . ?
C11 C12 C15 124.4(4) . . ?
O1 C13 C14 112.2(3) . . ?
N1 C14 C13 110.2(3) . . ?
C20 C15 C16 117.5(4) . . ?
C20 C15 C12 120.3(4) . . ?
C16 C15 C12 122.2(4) . . ?
C17 C16 C15 121.2(4) . . ?
C16 C17 C18 121.0(4) . . ?
N2 C18 C17 122.4(4) . . ?
N2 C18 C19 120.8(4) . . ?
C17 C18 C19 116.8(4) . . ?
C20 C19 C18 121.2(4) . . ?
C19 C20 C15 122.2(4) . . ?
C10 N1 C6 111.2(3) . . ?
C10 N1 C14 124.9(3) . . ?
C6 N1 C14 123.9(3) . . ?
C18 N2 C21 122.0(4) . . ?
C18 N2 C22 121.0(3) . . ?
C21 N2 C22 117.0(3) . . ?
C12 O1 C13 119.6(3) . . ?

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
C6 C1 C2 C3 0.3(5) . . . . ?
C7 C1 C2 C3 -179.7(4) . . . . ?
C1 C2 C3 C4 1.3(6) . . . . ?
C2 C3 C4 C5 -1.7(6) . . . . ?
C3 C4 C5 C6 0.5(6) . . . . ?
C2 C1 C6 C5 -1.5(5) . . . . ?
C7 C1 C6 C5 178.5(3) . . . . ?
C2 C1 C6 N1 179.0(3) . . . . ?
C7 C1 C6 N1 -1.0(4) . . . . ?
C4 C5 C6 C1 1.1(5) . . . . ?
C4 C5 C6 N1 -179.6(3) . . . . ?
C2 C1 C7 C10 -177.9(4) . . . . ?
C6 C1 C7 C10 2.2(4) . . . . ?
C2 C1 C7 C8 66.4(5) . . . . ?
C6 C1 C7 C8 -113.6(3) . . . . ?
C2 C1 C7 C9 -58.8(5) . . . . ?
C6 C1 C7 C9 121.3(3) . . . . ?
C1 C7 C10 N1 -2.7(4) . . . . ?
C8 C7 C10 N1 115.0(3) . . . . ?
C9 C7 C10 N1 -121.9(3) . . . . ?
C1 C7 C10 C11 175.5(3) . . . . ?
C8 C7 C10 C11 -66.8(4) . . . . ?
C9 C7 C10 C11 56.3(5) . . . . ?
N1 C10 C11 C12 -1.3(7) . . . . ?
C7 C10 C11 C12 -179.2(4) . . . . ?
C10 C11 C12 O1 -17.3(7) . . . . ?
C10 C11 C12 C15 160.4(4) . . . . ?
O1 C13 C14 N1 -84.1(4) . . . . ?
O1 C12 C15 C20 2.4(5) . . . . ?
C11 C12 C15 C20 -175.6(4) . . . . ?
O1 C12 C15 C16 -178.7(4) . . . . ?
C11 C12 C15 C16 3.3(6) . . . . ?
C20 C15 C16 C17 2.2(6) . . . . ?
C12 C15 C16 C17 -176.8(4) . . . . ?
C15 C16 C17 C18 1.0(6) . . . . ?
C16 C17 C18 N2 176.9(4) . . . . ?
C16 C17 C18 C19 -3.1(6) . . . . ?
N2 C18 C19 C20 -177.9(4) . . . . ?
C17 C18 C19 C20 2.2(6) . . . . ?
C18 C19 C20 C15 0.9(6) . . . . ?
C16 C15 C20 C19 -3.1(6) . . . . ?
C12 C15 C20 C19 175.8(4) . . . . ?
C11 C10 N1 C6 -175.8(3) . . . . ?
C7 C10 N1 C6 2.3(4) . . . . ?
C11 C10 N1 C14 2.8(6) . . . . ?
C7 C10 N1 C14 -179.2(3) . . . . ?
C1 C6 N1 C10 -0.8(4) . . . . ?
C5 C6 N1 C10 179.8(3) . . . . ?
C1 C6 N1 C14 -179.4(3) . . . . ?
C5 C6 N1 C14 1.2(6) . . . . ?
C13 C14 N1 C10 39.7(5) . . . . ?
C13 C14 N1 C6 -141.9(3) . . . . ?
C17 C18 N2 C21 0.4(6) . . . . ?
C19 C18 N2 C21 -179.5(4) . . . . ?
C17 C18 N2 C22 178.4(4) . . . . ?
C19 C18 N2 C22 -1.5(6) . . . . ?
C11 C12 O1 C13 -11.4(6) . . . . ?
C15 C12 O1 C13 170.6(3) . . . . ?
C14 C13 O1 C12 69.0(5) . . . . ?

_refine_diff_density_max         0.683
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_1_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc1pfph9
_database_code_depnum_ccdc_archive 'CCDC 1562291'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C9TC01199D 2019
_audit_update_record             
;
2017-07-14 deposited with the CCDC.	2019-07-10 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            'C21 H22 I N O2'
_chemical_formula_weight         447.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_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'

_cell_length_a                   9.4276(5)
_cell_length_b                   10.1879(5)
_cell_length_c                   11.1539(6)
_cell_angle_alpha                111.6410(10)
_cell_angle_beta                 97.790(2)
_cell_angle_gamma                99.874(2)
_cell_volume                     957.65(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2434
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      24.55

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.685
_shelx_estimated_absorpt_T_min   0.708
_shelx_estimated_absorpt_T_max   0.751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6501
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.012
_diffrn_reflns_theta_max         25.541
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3553
_reflns_number_gt                3000
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0386P)²+0.2341P] 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         3553
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0789
_refine_ls_wR_factor_gt          0.0732
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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 0.1296(3) 0.5447(3) 0.2271(3) 0.0333(7) Uani 1 1 d . . . . .
C2 C 0.0860(4) 0.3959(4) 0.1901(3) 0.0423(8) Uani 1 1 d . . . . .
H2 H 0.0491 0.3579 0.2468 0.051 Uiso 1 1 calc R U . . .
C3 C 0.0988(4) 0.3051(4) 0.0662(4) 0.0478(8) Uani 1 1 d . . . . .
H3 H 0.0695 0.2048 0.0395 0.057 Uiso 1 1 calc R U . . .
C4 C 0.1539(4) 0.3600(4) -0.0179(3) 0.0447(8) Uani 1 1 d . . . . .
H4 H 0.1624 0.2961 -0.0998 0.054 Uiso 1 1 calc R U . . .
C5 C 0.1972(4) 0.5089(4) 0.0163(3) 0.0390(7) Uani 1 1 d . . . . .
H5 H 0.2336 0.5466 -0.0408 0.047 Uiso 1 1 calc R U . . .
C6 C 0.1831(3) 0.5977(3) 0.1397(3) 0.0324(7) Uani 1 1 d . . . . .
C7 C 0.1998(3) 0.7999(3) 0.3252(3) 0.0304(6) Uani 1 1 d . . . . .
C8 C 0.1371(3) 0.6695(3) 0.3550(3) 0.0315(6) Uani 1 1 d . . . . .
C9 C 0.2457(4) 0.6626(4) 0.4676(3) 0.0434(8) Uani 1 1 d . . . . .
H9A H 0.2080 0.5772 0.4820 0.065 Uiso 1 1 calc R U . . .
H9B H 0.2572 0.7476 0.5470 0.065 Uiso 1 1 calc R U . . .
H9C H 0.3396 0.6587 0.4440 0.065 Uiso 1 1 calc R U . . .
C10 C -0.0136(4) 0.6780(4) 0.3906(4) 0.0457(8) Uani 1 1 d . . . . .
H10A H -0.0762 0.6930 0.3239 0.069 Uiso 1 1 calc R U . . .
H10B H -0.0008 0.7575 0.4744 0.069 Uiso 1 1 calc R U . . .
H10C H -0.0581 0.5887 0.3960 0.069 Uiso 1 1 calc R U . . .
C11 C 0.2760(4) 0.8457(3) 0.1375(3) 0.0405(8) Uani 1 1 d . . . . .
H11A H 0.2431 0.7929 0.0425 0.049 Uiso 1 1 calc R U . . .
H11B H 0.3830 0.8711 0.1585 0.049 Uiso 1 1 calc R U . . .
C12 C 0.2204(4) 0.9834(3) 0.1808(3) 0.0435(8) Uani 1 1 d . . . . .
H12A H 0.2237 1.0230 0.1141 0.052 Uiso 1 1 calc R U . . .
H12B H 0.1182 0.9591 0.1867 0.052 Uiso 1 1 calc R U . . .
C13 C 0.2894(3) 1.0727(3) 0.4162(3) 0.0334(7) Uani 1 1 d . . . . .
C14 C 0.2318(3) 0.9430(3) 0.4214(3) 0.0348(7) Uani 1 1 d . . . . .
H14 H 0.2100 0.9505 0.5022 0.042 Uiso 1 1 calc R U . . .
C15 C 0.3423(3) 1.2088(3) 0.5343(3) 0.0317(7) Uani 1 1 d . . . . .
C16 C 0.3780(3) 1.2096(3) 0.6608(3) 0.0365(7) Uani 1 1 d . . . . .
H16 H 0.3689 1.1216 0.6698 0.044 Uiso 1 1 calc R U . . .
C17 C 0.4261(4) 1.3370(3) 0.7712(3) 0.0386(7) Uani 1 1 d . . . . .
H17 H 0.4491 1.3348 0.8541 0.046 Uiso 1 1 calc R U . . .
C18 C 0.4404(3) 1.4703(3) 0.7595(3) 0.0336(7) Uani 1 1 d . . . . .
C19 C 0.4053(3) 1.4718(3) 0.6355(3) 0.0351(7) Uani 1 1 d . . . . .
H19 H 0.4149 1.5600 0.6268 0.042 Uiso 1 1 calc R U . . .
C20 C 0.3563(3) 1.3430(3) 0.5249(3) 0.0341(7) Uani 1 1 d . . . . .
H20 H 0.3321 1.3457 0.4424 0.041 Uiso 1 1 calc R U . . .
C21 C 0.5149(5) 1.7290(4) 0.8660(4) 0.0604(10) Uani 1 1 d . . . . .
H21A H 0.5789 1.7294 0.8061 0.091 Uiso 1 1 calc R U . . .
H21B H 0.5612 1.8033 0.9520 0.091 Uiso 1 1 calc R U . . .
H21C H 0.4236 1.7476 0.8347 0.091 Uiso 1 1 calc R U . . .
I1 I 0.19048(3) 0.94661(2) 0.80616(2) 0.05571(11) Uani 1 1 d . . . . .
N1 N 0.2219(3) 0.7529(3) 0.2031(2) 0.0319(6) Uani 1 1 d . . . . .
O1 O 0.3042(3) 1.0930(2) 0.3059(2) 0.0439(6) Uani 1 1 d . . . . .
O2 O 0.4864(3) 1.5904(2) 0.8737(2) 0.0442(6) 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
C1 C6 1.387(4) . ?
C1 C2 1.384(4) . ?
C1 C8 1.503(4) . ?
C2 C3 1.386(5) . ?
C3 C4 1.372(5) . ?
C4 C5 1.390(5) . ?
C5 C6 1.380(4) . ?
C6 N1 1.429(4) . ?
C7 N1 1.326(4) . ?
C7 C14 1.405(4) . ?
C7 C8 1.528(4) . ?
C8 C10 1.534(4) . ?
C8 C9 1.540(4) . ?
C11 N1 1.462(4) . ?
C11 C12 1.516(4) . ?
C12 O1 1.438(4) . ?
C13 O1 1.341(3) . ?
C13 C14 1.366(4) . ?
C13 C15 1.464(4) . ?
C15 C20 1.395(4) . ?
C15 C16 1.402(4) . ?
C16 C17 1.370(5) . ?
C17 C18 1.397(4) . ?
C18 O2 1.351(4) . ?
C18 C19 1.384(4) . ?
C19 C20 1.378(4) . ?
C21 O2 1.428(4) . ?

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 C1 C2 119.4(3) . . ?
C6 C1 C8 109.6(3) . . ?
C2 C1 C8 130.9(3) . . ?
C1 C2 C3 118.2(3) . . ?
C4 C3 C2 121.3(3) . . ?
C3 C4 C5 121.6(3) . . ?
C6 C5 C4 116.2(3) . . ?
C1 C6 C5 123.2(3) . . ?
C1 C6 N1 107.8(3) . . ?
C5 C6 N1 128.9(3) . . ?
N1 C7 C14 129.2(3) . . ?
N1 C7 C8 109.3(2) . . ?
C14 C7 C8 121.5(3) . . ?
C1 C8 C7 101.5(2) . . ?
C1 C8 C10 113.6(3) . . ?
C7 C8 C10 110.6(2) . . ?
C1 C8 C9 109.9(2) . . ?
C7 C8 C9 110.1(3) . . ?
C10 C8 C9 110.7(3) . . ?
N1 C11 C12 111.0(2) . . ?
O1 C12 C11 113.3(3) . . ?
O1 C13 C14 125.5(3) . . ?
O1 C13 C15 111.8(3) . . ?
C14 C13 C15 122.7(3) . . ?
C13 C14 C7 130.9(3) . . ?
C20 C15 C16 117.5(3) . . ?
C20 C15 C13 120.9(3) . . ?
C16 C15 C13 121.6(3) . . ?
C17 C16 C15 121.5(3) . . ?
C16 C17 C18 120.1(3) . . ?
O2 C18 C19 124.6(3) . . ?
O2 C18 C17 116.1(3) . . ?
C19 C18 C17 119.3(3) . . ?
C20 C19 C18 120.3(3) . . ?
C19 C20 C15 121.4(3) . . ?
C7 N1 C6 111.8(2) . . ?
C7 N1 C11 125.3(3) . . ?
C6 N1 C11 122.9(2) . . ?
C13 O1 C12 118.7(2) . . ?
C18 O2 C21 118.1(3) . . ?

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
C6 C1 C2 C3 0.5(5) . . . . ?
C8 C1 C2 C3 -176.3(3) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C2 C3 C4 C5 -1.0(5) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C2 C1 C6 C5 -0.8(5) . . . . ?
C8 C1 C6 C5 176.6(3) . . . . ?
C2 C1 C6 N1 -179.1(3) . . . . ?
C8 C1 C6 N1 -1.6(3) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
C4 C5 C6 N1 178.1(3) . . . . ?
C6 C1 C8 C7 1.0(3) . . . . ?
C2 C1 C8 C7 178.1(3) . . . . ?
C6 C1 C8 C10 119.7(3) . . . . ?
C2 C1 C8 C10 -63.2(4) . . . . ?
C6 C1 C8 C9 -115.6(3) . . . . ?
C2 C1 C8 C9 61.5(4) . . . . ?
N1 C7 C8 C1 0.0(3) . . . . ?
C14 C7 C8 C1 -177.3(3) . . . . ?
N1 C7 C8 C10 -120.9(3) . . . . ?
C14 C7 C8 C10 61.8(4) . . . . ?
N1 C7 C8 C9 116.4(3) . . . . ?
C14 C7 C8 C9 -60.9(4) . . . . ?
N1 C11 C12 O1 80.7(3) . . . . ?
O1 C13 C14 C7 13.0(5) . . . . ?
C15 C13 C14 C7 -167.4(3) . . . . ?
N1 C7 C14 C13 2.2(6) . . . . ?
C8 C7 C14 C13 178.9(3) . . . . ?
O1 C13 C15 C20 20.1(4) . . . . ?
C14 C13 C15 C20 -159.6(3) . . . . ?
O1 C13 C15 C16 -161.1(3) . . . . ?
C14 C13 C15 C16 19.2(5) . . . . ?
C20 C15 C16 C17 -0.5(5) . . . . ?
C13 C15 C16 C17 -179.3(3) . . . . ?
C15 C16 C17 C18 0.0(5) . . . . ?
C16 C17 C18 O2 179.1(3) . . . . ?
C16 C17 C18 C19 0.1(5) . . . . ?
O2 C18 C19 C20 -178.6(3) . . . . ?
C17 C18 C19 C20 0.2(4) . . . . ?
C18 C19 C20 C15 -0.8(5) . . . . ?
C16 C15 C20 C19 0.9(4) . . . . ?
C13 C15 C20 C19 179.7(3) . . . . ?
C14 C7 N1 C6 176.1(3) . . . . ?
C8 C7 N1 C6 -1.0(3) . . . . ?
C14 C7 N1 C11 -5.3(5) . . . . ?
C8 C7 N1 C11 177.7(3) . . . . ?
C1 C6 N1 C7 1.6(3) . . . . ?
C5 C6 N1 C7 -176.5(3) . . . . ?
C1 C6 N1 C11 -177.1(3) . . . . ?
C5 C6 N1 C11 4.8(5) . . . . ?
C12 C11 N1 C7 -34.1(4) . . . . ?
C12 C11 N1 C6 144.4(3) . . . . ?
C14 C13 O1 C12 17.7(5) . . . . ?
C15 C13 O1 C12 -161.9(3) . . . . ?
C11 C12 O1 C13 -72.4(4) . . . . ?
C19 C18 O2 C21 -6.4(5) . . . . ?
C17 C18 O2 C21 174.7(3) . . . . ?

_refine_diff_density_max         0.331
_refine_diff_density_min         -0.702
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_cqn1023
_audit_block_doi                 10.5517/ccdc.csd.cc1pfpjb
_database_code_depnum_ccdc_archive 'CCDC 1562292'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C9TC01199D 2019
_audit_update_record             
;
2017-07-14 deposited with the CCDC.	2019-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 N3 O3, I'
_chemical_formula_sum            'C22 H24 I N3 O3'
_chemical_formula_weight         505.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   6.4834(13)
_cell_length_b                   23.560(5)
_cell_length_c                   14.458(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.21(3)
_cell_angle_gamma                90.00
_cell_volume                     2173.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    17473
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      27.59

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    1.501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8288
_exptl_absorpt_correction_T_max  0.8644
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19917
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4975
_reflns_number_gt                4126
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL-97

_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)+(0.0311P)²+1.3048P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4975
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0774
_refine_ls_wR_factor_gt          0.0724
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_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
C1 C 0.9453(5) 0.44659(11) 1.10825(19) 0.0419(6) Uani 1 1 d . . .
C2 C 1.0994(4) 0.41595(12) 1.16508(19) 0.0436(6) Uani 1 1 d . . .
H2 H 1.1997 0.4348 1.2082 0.052 Uiso 1 1 calc R . .
C3 C 1.1056(4) 0.35741(12) 1.15825(19) 0.0396(6) Uani 1 1 d . . .
H3 H 1.2066 0.3358 1.1964 0.047 Uiso 1 1 calc R . .
C4 C 0.9515(4) 0.33284(10) 1.09070(17) 0.0317(5) Uani 1 1 d . . .
C5 C 0.7950(4) 0.36350(10) 1.03400(17) 0.0326(5) Uani 1 1 d . . .
C6 C 0.7881(4) 0.42160(11) 1.04287(18) 0.0388(6) Uani 1 1 d . . .
H6 H 0.6832 0.4431 1.0069 0.047 Uiso 1 1 calc R . .
C7 C 0.6568(4) 0.32333(10) 0.96926(17) 0.0316(5) Uani 1 1 d . . .
C8 C 0.6591(5) 0.33629(12) 0.86562(19) 0.0461(6) Uani 1 1 d . . .
H8A H 0.6101 0.3743 0.8515 0.069 Uiso 1 1 calc R . .
H8B H 0.5693 0.3100 0.8268 0.069 Uiso 1 1 calc R . .
H8C H 0.7995 0.3327 0.8536 0.069 Uiso 1 1 calc R . .
C9 C 0.4315(4) 0.32411(12) 0.9894(2) 0.0426(6) Uani 1 1 d . . .
H9A H 0.4333 0.3148 1.0541 0.064 Uiso 1 1 calc R . .
H9B H 0.3482 0.2968 0.9500 0.064 Uiso 1 1 calc R . .
H9C H 0.3724 0.3612 0.9764 0.064 Uiso 1 1 calc R . .
C10 C 0.7635(4) 0.26661(10) 0.99733(17) 0.0299(5) Uani 1 1 d . . .
C11 C 1.0610(4) 0.22992(11) 1.11193(19) 0.0386(6) Uani 1 1 d . . .
H11A H 0.9901 0.2102 1.1562 0.046 Uiso 1 1 calc R . .
H11B H 1.1889 0.2463 1.1466 0.046 Uiso 1 1 calc R . .
C12 C 1.1143(4) 0.18833(12) 1.0405(2) 0.0426(6) Uani 1 1 d . . .
H12A H 1.1332 0.2089 0.9845 0.051 Uiso 1 1 calc R . .
H12B H 1.2460 0.1699 1.0659 0.051 Uiso 1 1 calc R . .
C13 C 0.7672(4) 0.16034(11) 0.96707(17) 0.0336(5) Uani 1 1 d . . .
C14 C 0.6906(4) 0.21552(10) 0.95524(17) 0.0330(5) Uani 1 1 d . . .
H14 H 0.5681 0.2189 0.9111 0.040 Uiso 1 1 calc R . .
C15 C 0.6483(4) 0.11099(10) 0.92844(17) 0.0332(5) Uani 1 1 d . . .
C16 C 0.7402(4) 0.05652(11) 0.93544(19) 0.0403(6) Uani 1 1 d . . .
H16 H 0.8800 0.0528 0.9636 0.048 Uiso 1 1 calc R . .
C17 C 0.6305(4) 0.00908(11) 0.9021(2) 0.0426(6) Uani 1 1 d . . .
H17 H 0.6972 -0.0260 0.9082 0.051 Uiso 1 1 calc R . .
C18 C 0.4173(4) 0.01220(11) 0.85857(19) 0.0401(6) Uani 1 1 d . . .
C19 C 0.3253(4) 0.06696(12) 0.8515(2) 0.0434(6) Uani 1 1 d . . .
H19 H 0.1856 0.0709 0.8233 0.052 Uiso 1 1 calc R . .
C20 C 0.4369(4) 0.11414(11) 0.88529(19) 0.0390(6) Uani 1 1 d . . .
H20 H 0.3708 0.1493 0.8795 0.047 Uiso 1 1 calc R . .
C21 C 0.4040(6) -0.09027(13) 0.8252(3) 0.0614(9) Uani 1 1 d . . .
H21A H 0.5148 -0.0890 0.7891 0.092 Uiso 1 1 calc R . .
H21B H 0.3009 -0.1176 0.7981 0.092 Uiso 1 1 calc R . .
H21C H 0.4604 -0.1010 0.8887 0.092 Uiso 1 1 calc R . .
C22 C 0.0863(5) -0.03139(18) 0.7839(3) 0.0810(13) Uani 1 1 d . . .
H22A H 0.0142 -0.0096 0.8245 0.122 Uiso 1 1 calc R . .
H22B H 0.0283 -0.0690 0.7769 0.122 Uiso 1 1 calc R . .
H22C H 0.0702 -0.0134 0.7235 0.122 Uiso 1 1 calc R . .
I1 I 0.11327(3) 0.241262(9) 0.759793(14) 0.04663(8) Uani 1 1 d . . .
N1 N 0.9483(5) 0.50867(10) 1.11599(19) 0.0534(6) Uani 1 1 d . . .
N2 N 0.9264(3) 0.27495(9) 1.06598(14) 0.0313(4) Uani 1 1 d . . .
N3 N 0.3073(4) -0.03470(10) 0.8246(2) 0.0536(6) Uani 1 1 d . . .
O4 O 1.1058(4) 0.53139(10) 1.16024(18) 0.0699(7) Uani 1 1 d . . .
O5 O 0.7958(5) 0.53531(10) 1.0772(2) 0.0791(8) Uani 1 1 d . . .
O6 O 0.9557(3) 0.14579(8) 1.01525(14) 0.0440(4) 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
C1 C2 1.380(4) . ?
C1 C6 1.392(4) . ?
C1 N1 1.467(4) . ?
C2 C3 1.384(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(3) . ?
C4 N2 1.412(3) . ?
C5 C6 1.376(4) . ?
C5 C7 1.509(3) . ?
C6 H6 0.9300 . ?
C7 C10 1.526(3) . ?
C7 C8 1.532(3) . ?
C7 C9 1.539(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N2 1.330(3) . ?
C10 C14 1.393(3) . ?
C11 N2 1.457(3) . ?
C11 C12 1.507(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O6 1.436(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O6 1.339(3) . ?
C13 C14 1.391(3) . ?
C13 C15 1.451(3) . ?
C14 H14 0.9300 . ?
C15 C20 1.403(3) . ?
C15 C16 1.411(3) . ?
C16 C17 1.366(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.415(4) . ?
C17 H17 0.9300 . ?
C18 N3 1.359(3) . ?
C18 C19 1.418(4) . ?
C19 C20 1.368(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 N3 1.451(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 N3 1.451(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N1 O5 1.221(4) . ?
N1 O4 1.227(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 123.3(2) . . ?
C2 C1 N1 118.6(3) . . ?
C6 C1 N1 118.1(3) . . ?
C1 C2 C3 120.4(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 116.0(2) . . ?
C2 C3 H3 122.0 . . ?
C4 C3 H3 122.0 . . ?
C5 C4 C3 123.8(2) . . ?
C5 C4 N2 108.3(2) . . ?
C3 C4 N2 127.9(2) . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 C7 131.0(2) . . ?
C4 C5 C7 109.4(2) . . ?
C5 C6 C1 116.9(2) . . ?
C5 C6 H6 121.6 . . ?
C1 C6 H6 121.6 . . ?
C5 C7 C10 101.11(19) . . ?
C5 C7 C8 112.0(2) . . ?
C10 C7 C8 110.6(2) . . ?
C5 C7 C9 110.8(2) . . ?
C10 C7 C9 111.2(2) . . ?
C8 C7 C9 110.9(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C14 128.1(2) . . ?
N2 C10 C7 109.4(2) . . ?
C14 C10 C7 122.5(2) . . ?
N2 C11 C12 110.7(2) . . ?
N2 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
O6 C12 C11 112.8(2) . . ?
O6 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
O6 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
O6 C13 C14 125.2(2) . . ?
O6 C13 C15 111.6(2) . . ?
C14 C13 C15 123.2(2) . . ?
C13 C14 C10 131.9(2) . . ?
C13 C14 H14 114.1 . . ?
C10 C14 H14 114.1 . . ?
C20 C15 C16 116.5(2) . . ?
C20 C15 C13 122.6(2) . . ?
C16 C15 C13 120.8(2) . . ?
C17 C16 C15 122.1(2) . . ?
C17 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
C16 C17 C18 121.4(2) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
N3 C18 C17 121.8(3) . . ?
N3 C18 C19 121.8(3) . . ?
C17 C18 C19 116.4(2) . . ?
C20 C19 C18 121.6(2) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C15 121.9(2) . . ?
C19 C20 H20 119.0 . . ?
C15 C20 H20 119.0 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O5 N1 O4 123.1(3) . . ?
O5 N1 C1 118.6(3) . . ?
O4 N1 C1 118.2(3) . . ?
C10 N2 C4 111.9(2) . . ?
C10 N2 C11 124.4(2) . . ?
C4 N2 C11 123.7(2) . . ?
C18 N3 C21 122.2(3) . . ?
C18 N3 C22 121.3(3) . . ?
C21 N3 C22 116.5(3) . . ?
C13 O6 C12 120.0(2) . . ?

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
C6 C1 C2 C3 0.9(4) . . . . ?
N1 C1 C2 C3 -178.3(2) . . . . ?
C1 C2 C3 C4 1.0(4) . . . . ?
C2 C3 C4 C5 -1.7(4) . . . . ?
C2 C3 C4 N2 177.0(2) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
N2 C4 C5 C6 -178.5(2) . . . . ?
C3 C4 C5 C7 179.9(2) . . . . ?
N2 C4 C5 C7 1.0(3) . . . . ?
C4 C5 C6 C1 1.5(4) . . . . ?
C7 C5 C6 C1 -177.8(2) . . . . ?
C2 C1 C6 C5 -2.2(4) . . . . ?
N1 C1 C6 C5 177.0(2) . . . . ?
C6 C5 C7 C10 178.1(3) . . . . ?
C4 C5 C7 C10 -1.2(2) . . . . ?
C6 C5 C7 C8 60.4(4) . . . . ?
C4 C5 C7 C8 -119.0(2) . . . . ?
C6 C5 C7 C9 -64.0(3) . . . . ?
C4 C5 C7 C9 116.6(2) . . . . ?
C5 C7 C10 N2 1.1(2) . . . . ?
C8 C7 C10 N2 119.9(2) . . . . ?
C9 C7 C10 N2 -116.5(2) . . . . ?
C5 C7 C10 C14 -179.7(2) . . . . ?
C8 C7 C10 C14 -61.0(3) . . . . ?
C9 C7 C10 C14 62.7(3) . . . . ?
N2 C11 C12 O6 -84.1(3) . . . . ?
O6 C13 C14 C10 -10.7(4) . . . . ?
C15 C13 C14 C10 168.7(3) . . . . ?
N2 C10 C14 C13 -4.0(5) . . . . ?
C7 C10 C14 C13 177.0(3) . . . . ?
O6 C13 C15 C20 171.8(2) . . . . ?
C14 C13 C15 C20 -7.7(4) . . . . ?
O6 C13 C15 C16 -6.2(3) . . . . ?
C14 C13 C15 C16 174.4(2) . . . . ?
C20 C15 C16 C17 0.0(4) . . . . ?
C13 C15 C16 C17 178.1(3) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C16 C17 C18 N3 179.5(3) . . . . ?
C16 C17 C18 C19 0.0(4) . . . . ?
N3 C18 C19 C20 -179.6(3) . . . . ?
C17 C18 C19 C20 -0.1(4) . . . . ?
C18 C19 C20 C15 0.1(4) . . . . ?
C16 C15 C20 C19 -0.1(4) . . . . ?
C13 C15 C20 C19 -178.1(3) . . . . ?
C2 C1 N1 O5 -168.7(3) . . . . ?
C6 C1 N1 O5 12.1(4) . . . . ?
C2 C1 N1 O4 12.3(4) . . . . ?
C6 C1 N1 O4 -166.9(3) . . . . ?
C14 C10 N2 C4 -179.7(2) . . . . ?
C7 C10 N2 C4 -0.6(3) . . . . ?
C14 C10 N2 C11 -0.9(4) . . . . ?
C7 C10 N2 C11 178.2(2) . . . . ?
C5 C4 N2 C10 -0.2(3) . . . . ?
C3 C4 N2 C10 -179.1(2) . . . . ?
C5 C4 N2 C11 -179.0(2) . . . . ?
C3 C4 N2 C11 2.1(4) . . . . ?
C12 C11 N2 C10 43.7(3) . . . . ?
C12 C11 N2 C4 -137.7(2) . . . . ?
C17 C18 N3 C21 -4.2(4) . . . . ?
C19 C18 N3 C21 175.3(3) . . . . ?
C17 C18 N3 C22 177.2(3) . . . . ?
C19 C18 N3 C22 -3.3(5) . . . . ?
C14 C13 O6 C12 -14.7(4) . . . . ?
C15 C13 O6 C12 165.8(2) . . . . ?
C11 C12 O6 C13 67.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.697
_refine_diff_density_rms         0.091
