# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_HOFTPE3N
_database_code_depnum_ccdc_archive 'CCDC 1451588'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C6SC03177C 2016
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2016-10-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            HOFTPE3N
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H17 N3 O6'
_chemical_formula_sum            'C26 H17 N3 O6'
_chemical_formula_weight         467.42

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   14.7815(5)
_cell_length_b                   9.0701(3)
_cell_length_c                   21.2106(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.718(4)
_cell_angle_gamma                90
_cell_volume                     2723.50(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4354
_cell_measurement_theta_min      4.2710
_cell_measurement_theta_max      73.7870

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.689
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.63029
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6525
_diffrn_reflns_number            10606
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.290
_diffrn_reflns_theta_max         73.882
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5353
_reflns_number_gt                4087
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0812P)²+0.6069P] 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         5353
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1729
_refine_ls_wR_factor_gt          0.1601
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
C15 C 0.24206(10) 0.90385(17) 0.26068(8) 0.0407(3) Uani 1 1 d . . . . .
O32 O -0.22184(18) 1.0284(3) 0.04284(13) 0.1557(12) Uani 1 1 d . . . . .
C1 C 0.26769(11) 0.86061(19) 0.38094(8) 0.0446(4) Uani 1 1 d . . . . .
C16 C 0.33101(11) 0.96924(19) 0.27234(9) 0.0471(4) Uani 1 1 d . . . . .
H16 H 0.3609 1.0113 0.3142 0.056 Uiso 1 1 calc R U . . .
C7 C 0.19819(11) 0.89199(18) 0.31565(8) 0.0426(4) Uani 1 1 d . . . . .
O29 O -0.13738(18) 0.8379(3) 0.51263(14) 0.1441(11) Uani 1 1 d . . . . .
C6 C 0.28283(13) 0.9619(2) 0.43204(9) 0.0538(4) Uani 1 1 d . . . . .
H6 H 0.2454 1.0487 0.4271 0.065 Uiso 1 1 calc R U . . .
C20 C 0.20043(12) 0.84287(19) 0.19886(8) 0.0489(4) Uani 1 1 d . . . . .
H20 H 0.1397 0.7987 0.1897 0.059 Uiso 1 1 calc R U . . .
C9 C 0.03659(11) 0.9611(2) 0.24711(9) 0.0529(4) Uani 1 1 d . . . . .
C10 C -0.04240(13) 0.8765(2) 0.21550(11) 0.0692(6) Uani 1 1 d . . . . .
H10 H -0.0529 0.7848 0.2338 0.083 Uiso 1 1 calc R U . . .
C8 C 0.10480(11) 0.90632(19) 0.30920(9) 0.0481(4) Uani 1 1 d . . . . .
O35 O 0.49571(17) 0.8746(3) 0.60052(10) 0.1282(9) Uani 1 1 d . . . . .
C5 C 0.35322(16) 0.9354(3) 0.49059(9) 0.0661(5) Uani 1 1 d . . . . .
H5 H 0.3653 1.0046 0.5256 0.079 Uiso 1 1 calc R U . . .
C26 C 0.08815(15) 0.7459(2) 0.40202(10) 0.0628(5) Uani 1 1 d . . . . .
H26 H 0.1364 0.6836 0.3956 0.075 Uiso 1 1 calc R U . . .
C14 C 0.04834(12) 1.0974(2) 0.22079(10) 0.0596(5) Uani 1 1 d . . . . .
H14 H 0.1009 1.1569 0.2426 0.071 Uiso 1 1 calc R U . . .
C2 C 0.32190(13) 0.7327(2) 0.38948(9) 0.0569(5) Uani 1 1 d . . . . .
H2 H 0.3119 0.6640 0.3543 0.068 Uiso 1 1 calc R U . . .
C21 C 0.06212(12) 0.8702(2) 0.36284(9) 0.0531(4) Uani 1 1 d . . . . .
C22 C -0.01068(15) 0.9578(3) 0.37211(13) 0.0736(6) Uani 1 1 d . . . . .
H22 H -0.0312 1.0420 0.3451 0.088 Uiso 1 1 calc R U . . .
C19 C 0.24654(16) 0.8460(2) 0.15073(9) 0.0600(5) Uani 1 1 d . . . . .
H19 H 0.2173 0.8035 0.1089 0.072 Uiso 1 1 calc R U . . .
C17 C 0.37600(14) 0.9731(2) 0.22325(11) 0.0603(5) Uani 1 1 d . . . . .
H17 H 0.4359 1.0196 0.2313 0.072 Uiso 1 1 calc R U . . .
O31 O -0.13946(18) 1.2230(3) 0.04546(14) 0.1525(11) Uani 1 1 d . . . . .
O34 O 0.52339(18) 0.6620(3) 0.56390(10) 0.1428(11) Uani 1 1 d . . . . .
C4 C 0.40484(14) 0.8076(3) 0.49685(9) 0.0680(6) Uani 1 1 d . . . . .
C18 C 0.33393(16) 0.9096(2) 0.16271(10) 0.0640(5) Uani 1 1 d . . . . .
H18 H 0.3655 0.9101 0.1295 0.077 Uiso 1 1 calc R U . . .
C25 C 0.04560(19) 0.7103(3) 0.45017(12) 0.0792(7) Uani 1 1 d . . . . .
H25 H 0.0647 0.6257 0.4771 0.095 Uiso 1 1 calc R U . . .
C13 C -0.01506(14) 1.1481(2) 0.16345(12) 0.0702(6) Uani 1 1 d . . . . .
H13 H -0.0071 1.2419 0.1459 0.084 Uiso 1 1 calc R U . . .
N33 N 0.48096(17) 0.7795(3) 0.55816(10) 0.0975(7) Uani 1 1 d . . . . .
N30 N -0.15579(17) 1.1075(3) 0.06918(14) 0.1121(9) Uani 1 1 d . . . . .
C3 C 0.38948(15) 0.7037(3) 0.44764(10) 0.0697(6) Uani 1 1 d . . . . .
H3 H 0.4247 0.6145 0.4538 0.084 Uiso 1 1 calc R U . . .
O28 O -0.0395(3) 0.6604(3) 0.54591(16) 0.1608(13) Uani 1 1 d . . . . .
C11 C -0.10536(15) 0.9254(3) 0.15775(13) 0.0823(7) Uani 1 1 d . . . . .
H11 H -0.1585 0.8672 0.1359 0.099 Uiso 1 1 calc R U . . .
C12 C -0.09026(15) 1.0586(3) 0.13248(12) 0.0778(7) Uani 1 1 d . . . . .
C24 C -0.02496(18) 0.8006(3) 0.45804(13) 0.0788(7) Uani 1 1 d . . . . .
N27 N -0.0711(2) 0.7623(4) 0.50931(16) 0.1090(9) Uani 1 1 d . . . . .
C23 C -0.05333(16) 0.9225(3) 0.42071(14) 0.0852(8) Uani 1 1 d . . . . .
H23 H -0.1019 0.9833 0.4276 0.102 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C15 C20 1.393(2) . ?
C15 C16 1.398(2) . ?
C15 C7 1.492(2) . ?
O32 N30 1.211(3) . ?
C1 C6 1.389(2) . ?
C1 C2 1.392(2) . ?
C1 C7 1.495(2) . ?
C16 C17 1.388(3) . ?
C7 C8 1.354(2) . ?
O29 N27 1.215(4) . ?
C6 C5 1.393(3) . ?
C20 C19 1.381(3) . ?
C9 C14 1.388(3) . ?
C9 C10 1.396(3) . ?
C9 C8 1.495(2) . ?
C10 C11 1.381(3) . ?
C8 C21 1.488(2) . ?
O35 N33 1.219(3) . ?
C5 C4 1.373(3) . ?
C26 C25 1.383(3) . ?
C26 C21 1.388(3) . ?
C14 C13 1.383(3) . ?
C2 C3 1.371(3) . ?
C21 C22 1.397(3) . ?
C22 C23 1.392(3) . ?
C19 C18 1.370(3) . ?
C17 C18 1.381(3) . ?
O31 N30 1.216(3) . ?
O34 N33 1.225(3) . ?
C4 C3 1.376(3) . ?
C4 N33 1.476(3) . ?
C25 C24 1.373(3) . ?
C13 C12 1.380(3) . ?
N30 C12 1.480(3) . ?
O28 N27 1.210(4) . ?
C11 C12 1.366(3) . ?
C24 C23 1.354(4) . ?
C24 N27 1.481(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
C20 C15 C16 118.25(15) . . ?
C20 C15 C7 122.23(14) . . ?
C16 C15 C7 119.37(14) . . ?
C6 C1 C2 119.48(16) . . ?
C6 C1 C7 120.69(15) . . ?
C2 C1 C7 119.71(15) . . ?
C17 C16 C15 120.49(16) . . ?
C8 C7 C15 125.02(15) . . ?
C8 C7 C1 121.39(15) . . ?
C15 C7 C1 113.59(13) . . ?
C1 C6 C5 119.53(18) . . ?
C19 C20 C15 120.63(17) . . ?
C14 C9 C10 118.69(17) . . ?
C14 C9 C8 121.30(16) . . ?
C10 C9 C8 119.98(17) . . ?
C11 C10 C9 120.4(2) . . ?
C7 C8 C21 123.10(16) . . ?
C7 C8 C9 122.06(16) . . ?
C21 C8 C9 114.84(14) . . ?
C4 C5 C6 118.96(18) . . ?
C25 C26 C21 121.7(2) . . ?
C13 C14 C9 121.22(18) . . ?
C3 C2 C1 121.34(18) . . ?
C26 C21 C22 118.05(19) . . ?
C26 C21 C8 122.11(16) . . ?
C22 C21 C8 119.72(18) . . ?
C23 C22 C21 120.3(2) . . ?
C18 C19 C20 120.72(18) . . ?
C18 C17 C16 120.14(18) . . ?
C5 C4 C3 122.61(18) . . ?
C5 C4 N33 119.5(2) . . ?
C3 C4 N33 117.9(2) . . ?
C19 C18 C17 119.76(18) . . ?
C24 C25 C26 118.3(2) . . ?
C12 C13 C14 118.2(2) . . ?
O35 N33 O34 124.4(2) . . ?
O35 N33 C4 117.2(3) . . ?
O34 N33 C4 118.4(2) . . ?
O32 N30 O31 123.3(3) . . ?
O32 N30 C12 118.1(3) . . ?
O31 N30 C12 118.5(2) . . ?
C2 C3 C4 118.03(19) . . ?
C12 C11 C10 119.2(2) . . ?
C11 C12 C13 122.2(2) . . ?
C11 C12 N30 118.9(2) . . ?
C13 C12 N30 118.9(2) . . ?
C23 C24 C25 122.3(2) . . ?
C23 C24 N27 119.4(2) . . ?
C25 C24 N27 118.4(3) . . ?
O28 N27 O29 124.2(3) . . ?
O28 N27 C24 118.4(3) . . ?
O29 N27 C24 117.3(3) . . ?
C24 C23 C22 119.4(2) . . ?

_refine_diff_density_max         0.280
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.035



####################################################################### 
# 
# 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_HOFTPE4N
_database_code_depnum_ccdc_archive 'CCDC 1451589'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C6SC03177C 2016
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2016-10-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            HOFTPE4N
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H16 N4 O8'
_chemical_formula_sum            'C26 H16 N4 O8'
_chemical_formula_weight         512.43

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      tetragonal
_space_group_IT_number           86
_space_group_name_H-M_alt        'P 42/n'
_space_group_name_Hall           '-P 4bc'

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

_cell_length_a                   19.9155(2)
_cell_length_b                   19.9155(2)
_cell_length_c                   13.4286(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5326.15(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4570
_cell_measurement_theta_min      3.9400
_cell_measurement_theta_max      73.1010

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             2112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.822
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.75059
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6525
_diffrn_reflns_number            11147
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.138
_diffrn_reflns_theta_max         73.839
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5252
_reflns_number_gt                4115
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0782P)²+1.1396P] 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         5252
_refine_ls_number_parameters     343
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1594
_refine_ls_wR_factor_gt          0.1470
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.070
_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 1.00113(10) 0.44919(9) 0.12090(13) 0.0541(4) Uani 1 1 d . . . . .
C2 C 0.89471(10) 0.13021(10) -0.08196(14) 0.0569(4) Uani 1 1 d . . . . .
H2 H 0.8841 0.1693 -0.1194 0.068 Uiso 1 1 calc R U . . .
C3 C 0.88210(10) 0.06774(10) -0.12158(13) 0.0582(4) Uani 1 1 d . . . . .
H3 H 0.8634 0.0634 -0.1864 0.070 Uiso 1 1 calc R U . . .
C4 C 0.93821(10) 0.42151(10) 0.12922(13) 0.0555(4) Uani 1 1 d . . . . .
H4 H 0.9026 0.4458 0.1595 0.067 Uiso 1 1 calc R U . . .
C5 C 0.92300(9) 0.13687(9) 0.01281(13) 0.0518(4) Uani 1 1 d . . . . .
C6 C 0.93952(10) 0.20371(9) 0.05612(12) 0.0533(4) Uani 1 1 d . . . . .
C7 C 0.89695(10) 0.01171(10) -0.06596(14) 0.0575(4) Uani 1 1 d . . . . .
C8 C 1.04239(10) 0.35323(10) 0.03737(15) 0.0615(5) Uani 1 1 d . . . . .
H8 H 1.0779 0.3303 0.0044 0.074 Uiso 1 1 calc R U . . .
C9 C 0.98019(10) 0.32216(9) 0.04729(12) 0.0527(4) Uani 1 1 d . . . . .
N3 N 0.88606(10) -0.05402(10) -0.11086(14) 0.0708(5) Uani 1 1 d . . . . .
C11 C 0.93415(10) 0.07935(10) 0.06847(13) 0.0569(4) Uani 1 1 d . . . . .
H11 H 0.9503 0.0834 0.1348 0.068 Uiso 1 1 calc R U . . .
C12 C 0.92807(10) 0.35719(10) 0.09231(13) 0.0537(4) Uani 1 1 d . . . . .
H12 H 0.8851 0.3369 0.0979 0.064 Uiso 1 1 calc R U . . .
N2 N 1.01355(9) 0.51524(9) 0.16510(13) 0.0650(4) Uani 1 1 d . . . . .
O4 O 1.06498(9) 0.54475(9) 0.14326(16) 0.0905(6) Uani 1 1 d . . . . .
C15 C 0.92141(11) 0.21000(9) 0.16380(13) 0.0570(4) Uani 1 1 d . . . . .
C16 C 0.99530(10) 0.24556(9) -0.09899(13) 0.0534(4) Uani 1 1 d . . . . .
C17 C 0.97716(12) 0.29238(10) -0.17072(14) 0.0645(5) Uani 1 1 d . . . . .
H17 H 0.9493 0.3291 -0.1526 0.077 Uiso 1 1 calc R U . . .
O3 O 0.97277(10) 0.53752(10) 0.22416(15) 0.0932(6) Uani 1 1 d . . . . .
C20 C 1.03747(12) 0.19301(10) -0.12574(15) 0.0628(5) Uani 1 1 d . . . . .
H20 H 1.0516 0.1616 -0.0768 0.075 Uiso 1 1 calc R U . . .
C21 C 0.96993(10) 0.25379(9) 0.00488(13) 0.0529(4) Uani 1 1 d . . . . .
C22 C 0.92222(10) 0.01628(10) 0.02947(15) 0.0600(5) Uani 1 1 d . . . . .
H22 H 0.9312 -0.0230 0.0674 0.072 Uiso 1 1 calc R U . . .
C23 C 0.85508(12) 0.20187(12) 0.19290(16) 0.0684(5) Uani 1 1 d . . . . .
H23 H 0.8214 0.1940 0.1443 0.082 Uiso 1 1 calc R U . . .
C24 C 1.05328(10) 0.41675(11) 0.07467(15) 0.0629(5) Uani 1 1 d . . . . .
H24 H 1.0960 0.4376 0.0685 0.076 Uiso 1 1 calc R U . . .
C25 C 1.05911(13) 0.18619(11) -0.22336(16) 0.0699(6) Uani 1 1 d . . . . .
H25 H 1.0873 0.1499 -0.2423 0.084 Uiso 1 1 calc R U . . .
O5 O 0.90441(11) -0.10362(9) -0.06548(16) 0.0977(6) Uani 1 1 d . . . . .
C27 C 0.99894(14) 0.28642(12) -0.26797(15) 0.0734(6) Uani 1 1 d . . . . .
H27 H 0.9865 0.3186 -0.3169 0.088 Uiso 1 1 calc R U . . .
C28 C 0.97080(13) 0.21956(11) 0.23557(14) 0.0661(5) Uani 1 1 d . . . . .
H28 H 1.0163 0.2246 0.2159 0.079 Uiso 1 1 calc R U . . .
O8 O 1.05813(14) 0.27467(13) -0.45059(14) 0.1213(8) Uani 1 1 d . . . . .
C30 C 0.88812(16) 0.21471(11) 0.36176(15) 0.0784(7) Uani 1 1 d . . . . .
C31 C 0.95388(16) 0.22177(11) 0.33577(15) 0.0765(7) Uani 1 1 d . . . . .
H31 H 0.9874 0.2281 0.3852 0.092 Uiso 1 1 calc R U . . .
C32 C 1.03900(13) 0.23296(11) -0.29201(14) 0.0682(5) Uani 1 1 d . . . . .
N1 N 0.8690(2) 0.21879(12) 0.46808(18) 0.1080(10) Uani 1 1 d . . . . .
O1 O 0.81069(17) 0.21207(17) 0.48882(18) 0.1609(15) Uani 1 1 d D . . . .
C35 C 0.83791(14) 0.20526(12) 0.29262(18) 0.0800(7) Uani 1 1 d . . . . .
H35 H 0.7924 0.2012 0.3130 0.096 Uiso 1 1 calc R U . . .
O7 O 1.08264(17) 0.17209(12) -0.42234(16) 0.1357(10) Uani 1 1 d . . . . .
N4 N 1.06141(14) 0.22594(13) -0.39611(15) 0.0908(7) Uani 1 1 d . . . . .
O2 O 0.9131(2) 0.22611(14) 0.52939(15) 0.1472(13) Uani 1 1 d . . . . .
O9 O 0.85954(13) -0.05650(10) -0.19314(14) 0.1048(7) 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 C24 1.372(3) . ?
C1 C4 1.374(3) . ?
C1 N2 1.464(2) . ?
C2 C3 1.376(3) . ?
C2 C5 1.398(3) . ?
C3 C7 1.375(3) . ?
C4 C12 1.388(3) . ?
C5 C11 1.386(3) . ?
C5 C6 1.489(3) . ?
C6 C21 1.354(3) . ?
C6 C15 1.496(2) . ?
C7 C22 1.380(3) . ?
C7 N3 1.457(3) . ?
C8 C24 1.378(3) . ?
C8 C9 1.391(3) . ?
C9 C12 1.389(3) . ?
C9 C21 1.490(3) . ?
N3 O5 1.217(3) . ?
N3 O9 1.226(3) . ?
C11 C22 1.381(3) . ?
N2 O4 1.217(2) . ?
N2 O3 1.219(2) . ?
C15 C23 1.387(3) . ?
C15 C28 1.390(3) . ?
C16 C17 1.389(3) . ?
C16 C20 1.389(3) . ?
C16 C21 1.493(2) . ?
C17 C27 1.381(3) . ?
C20 C25 1.387(3) . ?
C23 C35 1.384(3) . ?
C25 C32 1.370(3) . ?
C27 C32 1.369(3) . ?
C28 C31 1.388(3) . ?
O8 N4 1.217(3) . ?
C30 C31 1.363(4) . ?
C30 C35 1.377(4) . ?
C30 N1 1.480(3) . ?
C32 N4 1.474(3) . ?
N1 O1 1.201(4) . ?
N1 O2 1.213(4) . ?
O7 N4 1.205(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
C24 C1 C4 122.59(18) . . ?
C24 C1 N2 118.61(18) . . ?
C4 C1 N2 118.79(17) . . ?
C3 C2 C5 120.74(18) . . ?
C7 C3 C2 118.98(17) . . ?
C1 C4 C12 118.29(17) . . ?
C11 C5 C2 118.50(17) . . ?
C11 C5 C6 119.52(16) . . ?
C2 C5 C6 121.95(16) . . ?
C21 C6 C5 123.95(16) . . ?
C21 C6 C15 122.50(17) . . ?
C5 C6 C15 113.52(15) . . ?
C3 C7 C22 121.96(18) . . ?
C3 C7 N3 118.18(17) . . ?
C22 C7 N3 119.85(18) . . ?
C24 C8 C9 120.91(18) . . ?
C12 C9 C8 118.93(17) . . ?
C12 C9 C21 121.53(17) . . ?
C8 C9 C21 119.47(17) . . ?
O5 N3 O9 123.2(2) . . ?
O5 N3 C7 118.50(19) . . ?
O9 N3 C7 118.25(19) . . ?
C22 C11 C5 121.31(17) . . ?
C4 C12 C9 120.67(18) . . ?
O4 N2 O3 122.80(19) . . ?
O4 N2 C1 118.59(18) . . ?
O3 N2 C1 118.58(18) . . ?
C23 C15 C28 119.63(18) . . ?
C23 C15 C6 119.49(18) . . ?
C28 C15 C6 120.74(19) . . ?
C17 C16 C20 118.94(17) . . ?
C17 C16 C21 119.10(17) . . ?
C20 C16 C21 121.94(17) . . ?
C27 C17 C16 121.1(2) . . ?
C25 C20 C16 120.42(19) . . ?
C6 C21 C9 122.68(16) . . ?
C6 C21 C16 123.04(17) . . ?
C9 C21 C16 114.27(15) . . ?
C7 C22 C11 118.35(18) . . ?
C35 C23 C15 120.2(2) . . ?
C1 C24 C8 118.55(19) . . ?
C32 C25 C20 118.6(2) . . ?
C32 C27 C17 118.2(2) . . ?
C31 C28 C15 120.3(2) . . ?
C31 C30 C35 122.6(2) . . ?
C31 C30 N1 119.3(3) . . ?
C35 C30 N1 118.1(3) . . ?
C30 C31 C28 118.6(2) . . ?
C27 C32 C25 122.71(19) . . ?
C27 C32 N4 118.3(2) . . ?
C25 C32 N4 119.0(2) . . ?
O1 N1 O2 123.8(3) . . ?
O1 N1 C30 117.8(3) . . ?
O2 N1 C30 118.3(3) . . ?
C30 C35 C23 118.7(2) . . ?
O7 N4 O8 123.6(2) . . ?
O7 N4 C32 117.9(2) . . ?
O8 N4 C32 118.6(2) . . ?

_refine_diff_density_max         0.248
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.035



####################################################################### 
# 
# 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_p4-2no2
_database_code_depnum_ccdc_archive 'CCDC 1451590'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C6SC03177C 2016
_audit_update_record             
;
2016-02-03 deposited with the CCDC.
2016-10-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H18 N2 O4'
_chemical_formula_weight         422.42

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      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                   10.52308(18)
_cell_length_b                   8.79827(18)
_cell_length_c                   22.9441(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.4899(16)
_cell_angle_gamma                90
_cell_volume                     2114.53(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4534
_cell_measurement_theta_min      3.8530
_cell_measurement_theta_max      73.6980

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.740
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7848
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.871
_diffrn_reflns_theta_max         73.853
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4139
_reflns_number_gt                3644
_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-2013 (Sheldrick, 2013)'
_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)+(0.0606P)²+0.4502P]
 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         4139
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1161
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
C2 C 0.14423(13) 0.54011(17) 0.37941(6) 0.0418(3) Uani 1 1 d . . . . .
H2 H 0.1885 0.6145 0.3608 0.050 Uiso 1 1 calc R U . . .
C8 C 0.34099(11) 0.39646(15) 0.30801(5) 0.0343(3) Uani 1 1 d . . . . .
C1 C 0.19726(12) 0.39554(15) 0.38726(5) 0.0354(3) Uani 1 1 d . . . . .
C9 C 0.23144(11) 0.42787(15) 0.26332(5) 0.0347(3) Uani 1 1 d . . . . .
C7 C 0.32215(12) 0.36103(15) 0.36425(5) 0.0349(3) Uani 1 1 d . . . . .
C5 C 0.01475(13) 0.32066(18) 0.43714(6) 0.0430(3) Uani 1 1 d . . . . .
H5 H -0.0288 0.2482 0.4570 0.052 Uiso 1 1 calc R U . . .
C21 C 0.46870(12) 0.40586(16) 0.28541(6) 0.0377(3) Uani 1 1 d . . . . .
C16 C 0.43230(12) 0.32446(17) 0.46523(6) 0.0407(3) Uani 1 1 d . . . . .
H16 H 0.3764 0.3945 0.4793 0.049 Uiso 1 1 calc R U . . .
C14 C 0.12719(12) 0.32945(16) 0.25747(6) 0.0397(3) Uani 1 1 d . . . . .
H14 H 0.1240 0.2476 0.2829 0.048 Uiso 1 1 calc R U . . .
C26 C 0.48520(14) 0.35412(17) 0.22912(7) 0.0463(3) Uani 1 1 d . . . . .
H26 H 0.4178 0.3065 0.2071 0.056 Uiso 1 1 calc R U . . .
C6 C 0.13229(13) 0.28748(16) 0.41761(6) 0.0396(3) Uani 1 1 d . . . . .
H6 H 0.1683 0.1920 0.4248 0.048 Uiso 1 1 calc R U . . .
C17 C 0.52570(13) 0.25802(18) 0.50373(6) 0.0437(3) Uani 1 1 d . . . . .
H17 H 0.5330 0.2829 0.5433 0.052 Uiso 1 1 calc R U . . .
C4 C -0.03606(12) 0.46341(18) 0.42643(6) 0.0417(3) Uani 1 1 d . . . . .
C18 C 0.60745(13) 0.15436(16) 0.48217(6) 0.0413(3) Uani 1 1 d . . . . .
C15 C 0.42076(12) 0.28796(15) 0.40579(5) 0.0350(3) Uani 1 1 d . . . . .
C19 C 0.59601(14) 0.11041(17) 0.42412(6) 0.0440(3) Uani 1 1 d . . . . .
H19 H 0.6504 0.0377 0.4108 0.053 Uiso 1 1 calc R U . . .
O29 O 0.71506(12) 0.11622(18) 0.57392(5) 0.0711(4) Uani 1 1 d . . . . .
C20 C 0.50203(13) 0.17670(16) 0.38638(6) 0.0405(3) Uani 1 1 d . . . . .
H20 H 0.4925 0.1469 0.3473 0.049 Uiso 1 1 calc R U . . .
C3 C 0.02752(14) 0.57531(18) 0.39859(6) 0.0453(3) Uani 1 1 d . . . . .
H3 H -0.0074 0.6719 0.3929 0.054 Uiso 1 1 calc R U . . .
O32 O -0.21178(12) 0.40763(17) 0.47565(7) 0.0764(4) Uani 1 1 d . . . . .
N27 N 0.71326(12) 0.09209(16) 0.52137(6) 0.0527(3) Uani 1 1 d . . . . .
N30 N -0.16197(12) 0.49996(19) 0.44566(6) 0.0536(3) Uani 1 1 d . . . . .
C10 C 0.23402(13) 0.54895(17) 0.22429(6) 0.0410(3) Uani 1 1 d . . . . .
H10 H 0.3034 0.6149 0.2271 0.049 Uiso 1 1 calc R U . . .
C13 C 0.02864(13) 0.35258(19) 0.21416(7) 0.0476(4) Uani 1 1 d . . . . .
H13 H -0.0405 0.2862 0.2108 0.057 Uiso 1 1 calc R U . . .
O28 O 0.79703(14) 0.02105(18) 0.49959(6) 0.0800(4) Uani 1 1 d . . . . .
C25 C 0.60040(17) 0.3728(2) 0.20572(8) 0.0624(5) Uani 1 1 d . . . . .
H25 H 0.6104 0.3368 0.1683 0.075 Uiso 1 1 calc R U . . .
O31 O -0.21064(12) 0.6222(2) 0.43117(6) 0.0781(4) Uani 1 1 d . . . . .
C22 C 0.57151(13) 0.47631(18) 0.31768(7) 0.0493(4) Uani 1 1 d . . . . .
H22 H 0.5630 0.5105 0.3555 0.059 Uiso 1 1 calc R U . . .
C11 C 0.13411(15) 0.5720(2) 0.18127(7) 0.0517(4) Uani 1 1 d . . . . .
H11 H 0.1360 0.6544 0.1560 0.062 Uiso 1 1 calc R U . . .
C12 C 0.03181(14) 0.4733(2) 0.17589(7) 0.0535(4) Uani 1 1 d . . . . .
H12 H -0.0346 0.4879 0.1467 0.064 Uiso 1 1 calc R U . . .
C24 C 0.70029(16) 0.4446(2) 0.23762(10) 0.0704(6) Uani 1 1 d . . . . .
H24 H 0.7773 0.4589 0.2215 0.085 Uiso 1 1 calc R U . . .
C23 C 0.68602(15) 0.4954(2) 0.29355(10) 0.0658(5) Uani 1 1 d . . . . .
H23 H 0.7540 0.5428 0.3152 0.079 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C3 1.3788(19) . ?
C2 C1 1.394(2) . ?
C8 C7 1.3603(18) . ?
C8 C21 1.4882(16) . ?
C8 C9 1.4935(17) . ?
C1 C6 1.3955(18) . ?
C1 C7 1.4937(17) . ?
C9 C10 1.3936(19) . ?
C9 C14 1.3940(19) . ?
C7 C15 1.4865(18) . ?
C5 C4 1.378(2) . ?
C5 C6 1.3863(19) . ?
C21 C26 1.396(2) . ?
C21 C22 1.396(2) . ?
C16 C17 1.386(2) . ?
C16 C15 1.3950(18) . ?
C14 C13 1.381(2) . ?
C26 C25 1.382(2) . ?
C17 C18 1.378(2) . ?
C4 C3 1.381(2) . ?
C4 N30 1.4715(17) . ?
C18 C19 1.381(2) . ?
C18 N27 1.4688(18) . ?
C15 C20 1.4003(19) . ?
C19 C20 1.380(2) . ?
O29 N27 1.2227(18) . ?
O32 N30 1.216(2) . ?
N27 O28 1.2255(18) . ?
N30 O31 1.224(2) . ?
C10 C11 1.387(2) . ?
C13 C12 1.380(2) . ?
C25 C24 1.376(3) . ?
C22 C23 1.384(2) . ?
C11 C12 1.380(2) . ?
C24 C23 1.380(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
C3 C2 C1 121.44(13) . . ?
C7 C8 C21 124.16(11) . . ?
C7 C8 C9 121.37(11) . . ?
C21 C8 C9 114.46(10) . . ?
C2 C1 C6 118.49(12) . . ?
C2 C1 C7 119.66(11) . . ?
C6 C1 C7 121.84(12) . . ?
C10 C9 C14 118.46(12) . . ?
C10 C9 C8 121.42(11) . . ?
C14 C9 C8 119.99(12) . . ?
C8 C7 C15 123.46(11) . . ?
C8 C7 C1 120.12(11) . . ?
C15 C7 C1 116.42(10) . . ?
C4 C5 C6 118.51(13) . . ?
C26 C21 C22 118.47(13) . . ?
C26 C21 C8 120.04(12) . . ?
C22 C21 C8 121.31(13) . . ?
C17 C16 C15 121.06(13) . . ?
C13 C14 C9 120.51(14) . . ?
C25 C26 C21 120.80(16) . . ?
C5 C6 C1 120.84(13) . . ?
C18 C17 C16 118.63(13) . . ?
C5 C4 C3 122.38(12) . . ?
C5 C4 N30 119.40(13) . . ?
C3 C4 N30 118.22(14) . . ?
C17 C18 C19 122.14(13) . . ?
C17 C18 N27 119.32(13) . . ?
C19 C18 N27 118.50(13) . . ?
C16 C15 C20 118.25(12) . . ?
C16 C15 C7 121.17(12) . . ?
C20 C15 C7 120.56(11) . . ?
C20 C19 C18 118.56(13) . . ?
C19 C20 C15 121.24(13) . . ?
C2 C3 C4 118.24(14) . . ?
O29 N27 O28 123.15(14) . . ?
O29 N27 C18 118.59(14) . . ?
O28 N27 C18 118.25(13) . . ?
O32 N30 O31 123.32(14) . . ?
O32 N30 C4 118.24(15) . . ?
O31 N30 C4 118.44(14) . . ?
C11 C10 C9 120.62(14) . . ?
C12 C13 C14 120.59(14) . . ?
C24 C25 C26 120.14(17) . . ?
C23 C22 C21 120.12(16) . . ?
C12 C11 C10 120.23(15) . . ?
C11 C12 C13 119.58(14) . . ?
C25 C24 C23 119.84(14) . . ?
C24 C23 C22 120.61(17) . . ?

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-2

