# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_shelx_as446
_database_code_depnum_ccdc_archive 'CCDC 1822005'
_audit_update_record             
;
2018-06-01 deposited with the CCDC.
2018-06-12 downloaded from the CCDC.
;
_vrf_THETM01_ALERT_3_A           
;
PROBLEM:  The value of sine(theta_max)/wavelength is less than 0.550
Calculated sin(theta_max)/wavelength = 0.4864           
RESPONSE: 
           The crystal diffraction at high angles is low due to the poor crystal quality
even with slow data acquisition times
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H32 N4 O9'
_chemical_formula_weight         616.61

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   9.764(2)
_cell_length_b                   14.740(3)
_cell_length_c                   24.007(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3455.0(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4063
_cell_measurement_theta_min      2
_cell_measurement_theta_max      30

_exptl_crystal_description       tabular
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.800
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD diffractometer'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            15535
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.188
_diffrn_reflns_theta_max         21.650
_diffrn_reflns_theta_full        21.650
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4032
_reflns_number_gt                3627
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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       'Apex data collection software'
_computing_cell_refinement       'SAINT software'
_computing_data_reduction        ?
_computing_structure_solution    'SIR-97 for Windows (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_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)+(0.0587P)²+0.6683P] 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     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1440 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(3)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4032
_refine_ls_number_parameters     406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1039
_refine_ls_wR_factor_gt          0.1000
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
O3 O 1.1984(3) 0.50509(19) 0.19021(12) 0.0666(8) Uani 1 1 d . . . . .
O1 O 1.1187(3) 0.3737(2) 0.27824(11) 0.0662(7) Uani 1 1 d . . . . .
N1 N 0.8036(3) 0.3996(2) 0.16822(12) 0.0512(8) Uani 1 1 d . . . . .
N2 N 0.9389(3) 0.2248(2) 0.16630(11) 0.0522(8) Uani 1 1 d . . . . .
O2 O 1.2940(3) 0.3811(2) 0.15462(13) 0.0805(9) Uani 1 1 d . . . . .
O5 O 0.8590(3) 0.3839(2) 0.34016(11) 0.0765(9) Uani 1 1 d . . . . .
O4 O 0.8702(4) 0.2332(2) 0.33853(12) 0.0856(9) Uani 1 1 d . . . . .
C7 C 1.0600(4) 0.2805(3) 0.15528(15) 0.0537(9) Uani 1 1 d . . . . .
H7A H 1.071030 0.286396 0.115283 0.064 Uiso 1 1 calc R U . . .
H7B H 1.139978 0.249043 0.169474 0.064 Uiso 1 1 calc R U . . .
C6 C 1.0561(4) 0.3760(2) 0.18092(14) 0.0480(9) Uani 1 1 d . . . . .
C2 C 0.8964(4) 0.3151(2) 0.25220(14) 0.0490(9) Uani 1 1 d . . . . .
C8 C 0.9569(5) 0.1343(3) 0.14110(16) 0.0628(11) Uani 1 1 d . . . . .
H8 H 1.047420 0.111595 0.151899 0.075 Uiso 1 1 calc R U . . .
C10 C 0.9544(4) 0.1430(3) 0.07809(15) 0.0589(10) Uani 1 1 d . . . . .
C3 C 0.9121(4) 0.2207(2) 0.22630(14) 0.0530(10) Uani 1 1 d . . . . .
H3A H 0.986928 0.189145 0.244491 0.064 Uiso 1 1 calc R U . . .
H3B H 0.829000 0.186168 0.232738 0.064 Uiso 1 1 calc R U . . .
C26 C 0.8734(4) 0.3046(3) 0.31470(16) 0.0586(10) Uani 1 1 d . . . . .
C28 C 0.6044(4) 0.2599(3) 0.19611(18) 0.0656(11) Uani 1 1 d . . . . .
H28 H 0.656984 0.248880 0.164521 0.079 Uiso 1 1 calc R U . . .
C1 C 1.0323(4) 0.3612(2) 0.24257(15) 0.0491(9) Uani 1 1 d . . . . .
C17 C 0.9612(4) 0.4622(3) 0.09841(15) 0.0536(10) Uani 1 1 d . . . . .
C5 C 0.9394(4) 0.4403(2) 0.15941(14) 0.0502(9) Uani 1 1 d . . . . .
H5 H 0.943743 0.497034 0.180586 0.060 Uiso 1 1 calc R U . . .
C22 C 0.9288(4) 0.3994(3) 0.05747(16) 0.0611(10) Uani 1 1 d . . . . .
H22 H 0.891864 0.343664 0.067705 0.073 Uiso 1 1 calc R U . . .
C4 C 0.7795(4) 0.3758(3) 0.22718(14) 0.0522(9) Uani 1 1 d . . . . .
H4 H 0.775141 0.432171 0.248749 0.063 Uiso 1 1 calc R U . . .
C24 C 1.1969(4) 0.4204(3) 0.17278(15) 0.0525(9) Uani 1 1 d . . . . .
C23 C 0.6442(4) 0.3269(3) 0.23366(16) 0.0572(10) Uani 1 1 d . . . . .
C16 C 0.6965(4) 0.4634(3) 0.15037(17) 0.0685(11) Uani 1 1 d . . . . .
H16A H 0.608072 0.436505 0.156195 0.103 Uiso 1 1 calc R U . . .
H16B H 0.703415 0.518268 0.171703 0.103 Uiso 1 1 calc R U . . .
H16C H 0.708014 0.477006 0.111545 0.103 Uiso 1 1 calc R U . . .
C11 C 0.8335(4) 0.1604(3) 0.04981(17) 0.0678(12) Uani 1 1 d . . . . .
H11 H 0.752588 0.167947 0.069729 0.081 Uiso 1 1 calc R U . . .
C20 C 1.0040(5) 0.5006(4) -0.01231(18) 0.0801(14) Uani 1 1 d . . . . .
C19 C 1.0369(6) 0.5633(4) 0.0263(2) 0.0912(15) Uani 1 1 d . . . . .
H19 H 1.073233 0.618921 0.015570 0.109 Uiso 1 1 calc R U . . .
C32 C 0.5612(4) 0.3438(3) 0.27929(18) 0.0687(12) Uani 1 1 d . . . . .
H32 H 0.584760 0.389741 0.304022 0.082 Uiso 1 1 calc R U . . .
C9 C 0.8509(6) 0.0663(3) 0.16095(19) 0.0879(15) Uani 1 1 d . . . . .
H9A H 0.867087 0.008724 0.143399 0.132 Uiso 1 1 calc R U . . .
H9B H 0.857609 0.059541 0.200636 0.132 Uiso 1 1 calc R U . . .
H9C H 0.760976 0.087476 0.151387 0.132 Uiso 1 1 calc R U . . .
C21 C 0.9504(5) 0.4180(4) 0.00180(17) 0.0716(12) Uani 1 1 d . . . . .
H21 H 0.929055 0.375478 -0.025446 0.086 Uiso 1 1 calc R U . . .
N3 N 1.0263(6) 0.5217(5) -0.0729(2) 0.1131(16) Uani 1 1 d . . . . .
C30 C 0.4121(5) 0.2263(3) 0.2531(2) 0.0737(13) Uani 1 1 d . . . . .
C29 C 0.4864(5) 0.2094(3) 0.2056(2) 0.0797(14) Uani 1 1 d . . . . .
H29 H 0.458514 0.165141 0.180446 0.096 Uiso 1 1 calc R U . . .
C18 C 1.0161(5) 0.5439(3) 0.08241(19) 0.0745(12) Uani 1 1 d . . . . .
H18 H 1.039441 0.586671 0.109269 0.089 Uiso 1 1 calc R U . . .
C31 C 0.4439(5) 0.2935(4) 0.2888(2) 0.0799(13) Uani 1 1 d . . . . .
H31 H 0.388057 0.305862 0.319262 0.096 Uiso 1 1 calc R U . . .
C25 C 1.3310(5) 0.5501(4) 0.1867(2) 0.0928(16) Uani 1 1 d . . . . .
H25A H 1.322770 0.611201 0.200162 0.139 Uiso 1 1 calc R U . . .
H25B H 1.396482 0.517810 0.208971 0.139 Uiso 1 1 calc R U . . .
H25C H 1.361094 0.551017 0.148626 0.139 Uiso 1 1 calc R U . . .
C15 C 1.0705(5) 0.1327(3) 0.04688(19) 0.0807(13) Uani 1 1 d . . . . .
H15 H 1.153128 0.120489 0.064606 0.097 Uiso 1 1 calc R U . . .
C27 C 0.8422(7) 0.3808(5) 0.40019(19) 0.119(2) Uani 1 1 d . . . . .
H27A H 0.832680 0.441372 0.414343 0.178 Uiso 1 1 calc R U . . .
H27B H 0.761750 0.346323 0.409209 0.178 Uiso 1 1 calc R U . . .
H27C H 0.920958 0.352617 0.416717 0.178 Uiso 1 1 calc R U . . .
C14 C 1.0674(6) 0.1402(4) -0.0109(2) 0.1053(19) Uani 1 1 d . . . . .
H14 H 1.147634 0.134121 -0.031425 0.126 Uiso 1 1 calc R U . . .
C12 C 0.8317(5) 0.1665(4) -0.0070(2) 0.0851(14) Uani 1 1 d . . . . .
H12 H 0.749446 0.177820 -0.025317 0.102 Uiso 1 1 calc R U . . .
C13 C 0.9478(7) 0.1564(4) -0.0369(2) 0.1008(18) Uani 1 1 d . . . . .
H13 H 0.945124 0.160586 -0.075508 0.121 Uiso 1 1 calc R U . . .
N4 N 0.2893(5) 0.1696(4) 0.2633(3) 0.1025(16) Uani 1 1 d . . . . .
O9 O 0.2268(5) 0.1814(3) 0.3074(3) 0.1386(18) Uani 1 1 d . . . . .
O8 O 0.2604(5) 0.1116(4) 0.2291(2) 0.1388(19) Uani 1 1 d . . . . .
O6 O 1.0783(8) 0.5923(5) -0.0839(2) 0.198(3) Uani 1 1 d . . . . .
O7 O 0.9915(6) 0.4661(4) -0.10589(19) 0.153(2) 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
O3 C24 1.317(5) . ?
O3 C25 1.457(5) . ?
O1 C1 1.216(4) . ?
N1 C5 1.470(5) . ?
N1 C16 1.470(5) . ?
N1 C4 1.477(5) . ?
N2 C7 1.464(5) . ?
N2 C3 1.465(5) . ?
N2 C8 1.476(5) . ?
O2 C24 1.194(5) . ?
O5 C26 1.326(5) . ?
O5 C27 1.451(5) . ?
O4 C26 1.198(5) . ?
C7 C6 1.536(5) . ?
C6 C1 1.514(5) . ?
C6 C24 1.535(5) . ?
C6 C5 1.569(5) . ?
C2 C1 1.508(5) . ?
C2 C26 1.525(5) . ?
C2 C3 1.533(5) . ?
C2 C4 1.569(5) . ?
C8 C9 1.517(6) . ?
C8 C10 1.518(5) . ?
C10 C15 1.367(6) . ?
C10 C11 1.386(6) . ?
C28 C29 1.391(6) . ?
C28 C23 1.393(6) . ?
C17 C18 1.373(6) . ?
C17 C22 1.387(5) . ?
C17 C5 1.515(5) . ?
C22 C21 1.381(6) . ?
C4 C23 1.512(6) . ?
C23 C32 1.385(6) . ?
C11 C12 1.368(6) . ?
C20 C19 1.348(7) . ?
C20 C21 1.367(7) . ?
C20 N3 1.503(7) . ?
C19 C18 1.392(6) . ?
C32 C31 1.383(6) . ?
N3 O6 1.187(7) . ?
N3 O7 1.189(7) . ?
C30 C31 1.347(7) . ?
C30 C29 1.373(7) . ?
C30 N4 1.482(7) . ?
C15 C14 1.391(7) . ?
C14 C13 1.345(8) . ?
C12 C13 1.350(7) . ?
N4 O8 1.220(7) . ?
N4 O9 1.233(7) . ?

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 O3 C25 115.1(3) . . ?
C5 N1 C16 109.8(3) . . ?
C5 N1 C4 112.2(3) . . ?
C16 N1 C4 108.5(3) . . ?
C7 N2 C3 110.2(3) . . ?
C7 N2 C8 109.7(3) . . ?
C3 N2 C8 112.7(3) . . ?
C26 O5 C27 116.2(4) . . ?
N2 C7 C6 114.9(3) . . ?
C1 C6 C24 108.9(3) . . ?
C1 C6 C7 105.3(3) . . ?
C24 C6 C7 108.4(3) . . ?
C1 C6 C5 107.3(3) . . ?
C24 C6 C5 110.6(3) . . ?
C7 C6 C5 116.1(3) . . ?
C1 C2 C26 109.0(3) . . ?
C1 C2 C3 105.0(3) . . ?
C26 C2 C3 108.7(3) . . ?
C1 C2 C4 109.0(3) . . ?
C26 C2 C4 109.1(3) . . ?
C3 C2 C4 115.8(3) . . ?
N2 C8 C9 112.8(3) . . ?
N2 C8 C10 109.2(3) . . ?
C9 C8 C10 111.0(3) . . ?
C15 C10 C11 117.3(4) . . ?
C15 C10 C8 121.6(4) . . ?
C11 C10 C8 121.2(4) . . ?
N2 C3 C2 112.3(3) . . ?
O4 C26 O5 123.4(3) . . ?
O4 C26 C2 124.3(4) . . ?
O5 C26 C2 112.3(4) . . ?
C29 C28 C23 120.3(4) . . ?
O1 C1 C2 124.8(3) . . ?
O1 C1 C6 124.0(3) . . ?
C2 C1 C6 110.5(3) . . ?
C18 C17 C22 118.5(4) . . ?
C18 C17 C5 120.8(4) . . ?
C22 C17 C5 120.7(4) . . ?
N1 C5 C17 110.7(3) . . ?
N1 C5 C6 111.2(3) . . ?
C17 C5 C6 110.2(3) . . ?
C21 C22 C17 121.2(4) . . ?
N1 C4 C23 110.6(3) . . ?
N1 C4 C2 112.7(3) . . ?
C23 C4 C2 108.9(3) . . ?
O2 C24 O3 124.5(4) . . ?
O2 C24 C6 123.5(4) . . ?
O3 C24 C6 111.9(3) . . ?
C32 C23 C28 118.4(4) . . ?
C32 C23 C4 120.5(4) . . ?
C28 C23 C4 121.0(4) . . ?
C12 C11 C10 120.8(4) . . ?
C19 C20 C21 122.1(4) . . ?
C19 C20 N3 119.3(5) . . ?
C21 C20 N3 118.7(5) . . ?
C20 C19 C18 119.3(5) . . ?
C31 C32 C23 121.3(4) . . ?
C20 C21 C22 118.4(4) . . ?
O6 N3 O7 125.3(6) . . ?
O6 N3 C20 117.3(6) . . ?
O7 N3 C20 117.4(6) . . ?
C31 C30 C29 122.7(4) . . ?
C31 C30 N4 119.7(5) . . ?
C29 C30 N4 117.6(5) . . ?
C30 C29 C28 118.5(4) . . ?
C17 C18 C19 120.5(5) . . ?
C30 C31 C32 118.7(4) . . ?
C10 C15 C14 121.3(5) . . ?
C13 C14 C15 119.7(5) . . ?
C13 C12 C11 120.8(4) . . ?
C14 C13 C12 120.2(5) . . ?
O8 N4 O9 124.2(6) . . ?
O8 N4 C30 118.0(6) . . ?
O9 N4 C30 117.6(6) . . ?

_refine_diff_density_max         0.130
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.031



####################################################################### 
# 
# 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_ls028_fio
_database_code_depnum_ccdc_archive 'CCDC 1822006'
_audit_update_record             
;
2018-06-01 deposited with the CCDC.
2018-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H36 N2 O'
_chemical_formula_weight         500.66

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   10.517(5)
_cell_length_b                   11.646(5)
_cell_length_c                   22.808(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2793.5(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4063
_cell_measurement_theta_min      2
_cell_measurement_theta_max      30

_exptl_crystal_description       tabular
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD diffractometer'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            30161
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.786
_diffrn_reflns_theta_max         31.855
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8970
_reflns_number_gt                7288
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_max     0.912
_reflns_Friedel_fraction_full    1.000

_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       'Apex data collection software'
_computing_cell_refinement       'SAINT software'
_computing_data_reduction        ?
_computing_structure_solution    'SIR-97 for Windows (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_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)+(0.0636P)²+0.2016P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2623 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(3)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         8970
_refine_ls_number_parameters     487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1190
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
O1 O 0.33723(12) 0.00434(13) 0.46179(5) 0.0457(3) Uani 1 1 d . . . . .
N2 N 0.15359(13) -0.19142(11) 0.35847(6) 0.0350(3) Uani 1 1 d . . . . .
N1 N 0.35056(14) 0.03102(12) 0.30727(6) 0.0355(3) Uani 1 1 d . . . . .
C30 C 0.13210(16) 0.11887(14) 0.41291(7) 0.0345(3) Uani 1 1 d . . . . .
C5 C 0.39632(17) -0.08560(16) 0.31643(7) 0.0365(3) Uani 1 1 d . . . . .
C4 C 0.21307(16) 0.03677(15) 0.31707(7) 0.0342(3) Uani 1 1 d . . . . .
C16 C 0.4003(2) 0.07956(18) 0.25176(8) 0.0446(4) Uani 1 1 d . . . . .
C8 C 0.06350(19) -0.28881(16) 0.35263(9) 0.0429(4) Uani 1 1 d . . . . .
C3 C 0.09683(16) -0.09381(14) 0.38869(8) 0.0346(3) Uani 1 1 d . . . . .
C2 C 0.18487(14) 0.01208(13) 0.38299(7) 0.0307(3) Uani 1 1 d . . . . .
C7 C 0.27635(16) -0.22537(15) 0.38306(8) 0.0363(3) Uani 1 1 d . . . . .
C6 C 0.37282(14) -0.12558(14) 0.38078(7) 0.0325(3) Uani 1 1 d . . . . .
C10 C 0.1070(2) -0.36711(17) 0.30291(9) 0.0467(4) Uani 1 1 d . . . . .
C18 C 0.37948(19) 0.00549(17) 0.19759(8) 0.0429(4) Uani 1 1 d . . . . .
C1 C 0.30670(14) -0.02753(14) 0.41373(7) 0.0313(3) Uani 1 1 d . . . . .
C25 C 0.5348(3) -0.2677(3) 0.42235(9) 0.0622(7) Uani 1 1 d . . . . .
C24 C 0.49959(17) -0.15647(19) 0.40925(7) 0.0440(4) Uani 1 1 d . . . . .
C31 C 0.2063(2) 0.21747(17) 0.41353(10) 0.0469(4) Uani 1 1 d . . . . .
C34 C -0.0291(2) 0.2262(2) 0.46489(11) 0.0583(6) Uani 1 1 d . . . . .
C29 C 0.58667(19) -0.0687(3) 0.41926(10) 0.0641(7) Uani 1 1 d . . . . .
C32 C 0.1628(2) 0.31797(18) 0.43943(11) 0.0563(5) Uani 1 1 d . . . . .
C11 C 0.1021(2) -0.4859(2) 0.30792(12) 0.0579(5) Uani 1 1 d . . . . .
C12 C 0.1408(3) -0.5557(3) 0.26179(15) 0.0739(8) Uani 1 1 d . . . . .
C33 C 0.0443(2) 0.3221(2) 0.46510(9) 0.0561(6) Uani 1 1 d . . . . .
C35 C 0.01367(19) 0.12399(19) 0.43909(9) 0.0473(4) Uani 1 1 d . . . . .
C23 C 0.4826(3) -0.0431(3) 0.16915(10) 0.0650(7) Uani 1 1 d . . . . .
C20 C 0.2422(3) -0.0805(3) 0.12499(11) 0.0709(7) Uani 1 1 d . . . . .
C9 C 0.0384(3) -0.3523(2) 0.41024(11) 0.0578(6) Uani 1 1 d . . . . .
C19 C 0.2594(2) -0.0140(2) 0.17452(9) 0.0537(5) Uani 1 1 d . . . . .
C28 C 0.7060(2) -0.0926(5) 0.44252(13) 0.0954(13) Uani 1 1 d . . . . .
C26 C 0.6565(4) -0.2905(4) 0.44448(12) 0.0930(13) Uani 1 1 d . . . . .
C17 C 0.3533(4) 0.2016(2) 0.24174(13) 0.0698(8) Uani 1 1 d . . . . .
C15 C 0.1501(3) -0.3213(3) 0.25054(11) 0.0702(7) Uani 1 1 d . . . . .
C14 C 0.1908(4) -0.3926(3) 0.20535(13) 0.0862(10) Uani 1 1 d . . . . .
C21 C 0.3453(4) -0.1281(3) 0.09718(13) 0.0867(10) Uani 1 1 d . . . . .
C13 C 0.1866(3) -0.5091(3) 0.21131(14) 0.0805(9) Uani 1 1 d . . . . .
C22 C 0.4643(3) -0.1089(3) 0.11903(13) 0.0882(11) Uani 1 1 d . . . . .
C27 C 0.7410(3) -0.2036(5) 0.45453(12) 0.1086(17) Uani 1 1 d . . . . .
H3 H 0.271(2) -0.2514(18) 0.4235(10) 0.041(5) Uiso 1 1 d . . . . .
H1 H 0.015(2) -0.0794(19) 0.3717(9) 0.040(5) Uiso 1 1 d . . . . .
H8 H 0.487(2) -0.089(2) 0.3070(10) 0.047(6) Uiso 1 1 d . . . . .
H10 H 0.184(2) 0.1124(19) 0.3076(9) 0.036(5) Uiso 1 1 d . . . . .
H4 H 0.309(2) -0.290(2) 0.3590(9) 0.042(5) Uiso 1 1 d . . . . .
H2 H 0.083(2) -0.1063(18) 0.4304(10) 0.041(5) Uiso 1 1 d . . . . .
H9 H 0.357(2) -0.1415(19) 0.2902(10) 0.041(5) Uiso 1 1 d . . . . .
H11 H 0.1680(19) -0.0175(17) 0.2920(9) 0.032(5) Uiso 1 1 d . . . . .
H5 H -0.034(3) -0.400(3) 0.4064(12) 0.067(8) Uiso 1 1 d . . . . .
H7 H 0.024(3) -0.302(2) 0.4417(13) 0.062(7) Uiso 1 1 d . . . . .
H13 H -0.037(2) 0.060(2) 0.4412(10) 0.050(6) Uiso 1 1 d . . . . .
H6 H 0.115(3) -0.404(2) 0.4218(12) 0.066(8) Uiso 1 1 d . . . . .
H18 H -0.014(2) -0.2527(19) 0.3398(10) 0.045(6) Uiso 1 1 d . . . . .
H14 H -0.116(3) 0.223(3) 0.4820(14) 0.091(10) Uiso 1 1 d . . . . .
H12 H 0.490(3) 0.082(2) 0.2574(12) 0.058(7) Uiso 1 1 d . . . . .
H17 H 0.289(3) 0.217(2) 0.3961(11) 0.061(7) Uiso 1 1 d . . . . .
H16 H 0.217(3) 0.388(3) 0.4396(13) 0.071(8) Uiso 1 1 d . . . . .
H33 H 0.016(3) 0.397(2) 0.4824(12) 0.061(7) Uiso 1 1 d . . . . .
H30 H 0.212(3) -0.555(3) 0.1809(16) 0.091(10) Uiso 1 1 d . . . . .
H29 H 0.220(3) -0.356(3) 0.1705(16) 0.082(9) Uiso 1 1 d . . . . .
H22 H 0.564(3) -0.027(2) 0.1858(11) 0.058(7) Uiso 1 1 d . . . . .
H19 H 0.393(3) 0.239(3) 0.2104(17) 0.094(11) Uiso 1 1 d . . . . .
H21 H 0.368(3) 0.245(3) 0.2778(14) 0.073(9) Uiso 1 1 d . . . . .
H26 H 0.184(3) 0.015(2) 0.1952(12) 0.059(7) Uiso 1 1 d . . . . .
H281 H 0.146(3) -0.240(3) 0.2444(14) 0.082(10) Uiso 1 1 d . . . . .
H27 H 0.082(3) -0.515(3) 0.3449(16) 0.089(10) Uiso 1 1 d . . . . .
H339 H 0.767(5) -0.030(4) 0.4505(19) 0.126(14) Uiso 1 1 d . . . . .
H25 H 0.154(4) -0.096(3) 0.1125(16) 0.095(11) Uiso 1 1 d . . . . .
H32 H 0.558(4) 0.013(3) 0.4084(14) 0.086(10) Uiso 1 1 d . . . . .
H24 H 0.334(3) -0.173(3) 0.0607(17) 0.090(10) Uiso 1 1 d . . . . .
H23 H 0.537(5) -0.136(4) 0.099(2) 0.124(14) Uiso 1 1 d . . . . .
H31 H 0.477(3) -0.329(2) 0.4159(12) 0.060(8) Uiso 1 1 d . . . . .
H20 H 0.254(4) 0.200(3) 0.2276(14) 0.091(11) Uiso 1 1 d . . . . .
H36 H 0.137(4) -0.640(3) 0.2672(17) 0.103(12) Uiso 1 1 d . . . . .
H34 H 0.662(4) -0.364(3) 0.4499(17) 0.093(12) Uiso 1 1 d . . . . .
H35 H 0.818(4) -0.225(4) 0.4708(16) 0.110(12) 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
O1 C1 1.201(2) . ?
N2 C3 1.457(2) . ?
N2 C7 1.462(2) . ?
N2 C8 1.484(2) . ?
N1 C5 1.456(2) . ?
N1 C4 1.465(2) . ?
N1 C16 1.482(2) . ?
C30 C35 1.383(3) . ?
C30 C31 1.388(3) . ?
C30 C2 1.523(2) . ?
C5 C6 1.559(2) . ?
C4 C2 1.559(2) . ?
C16 C17 1.522(3) . ?
C16 C18 1.523(3) . ?
C8 C10 1.525(3) . ?
C8 C9 1.531(3) . ?
C3 C2 1.548(2) . ?
C2 C1 1.532(2) . ?
C7 C6 1.544(2) . ?
C6 C24 1.526(2) . ?
C6 C1 1.534(2) . ?
C10 C15 1.384(4) . ?
C10 C11 1.389(3) . ?
C18 C23 1.385(3) . ?
C18 C19 1.387(3) . ?
C25 C24 1.380(4) . ?
C25 C26 1.401(4) . ?
C24 C29 1.391(3) . ?
C31 C32 1.389(3) . ?
C34 C33 1.358(4) . ?
C34 C35 1.402(3) . ?
C29 C28 1.391(4) . ?
C32 C33 1.378(4) . ?
C11 C12 1.391(4) . ?
C12 C13 1.360(5) . ?
C23 C22 1.389(4) . ?
C20 C21 1.372(4) . ?
C20 C19 1.382(3) . ?
C28 C27 1.372(7) . ?
C26 C27 1.366(7) . ?
C15 C14 1.391(4) . ?
C14 C13 1.364(5) . ?
C21 C22 1.366(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
C3 N2 C7 113.03(13) . . ?
C3 N2 C8 112.16(14) . . ?
C7 N2 C8 113.05(14) . . ?
C5 N1 C4 110.31(14) . . ?
C5 N1 C16 111.21(14) . . ?
C4 N1 C16 117.49(14) . . ?
C35 C30 C31 117.79(17) . . ?
C35 C30 C2 123.84(16) . . ?
C31 C30 C2 118.37(15) . . ?
N1 C5 C6 111.18(13) . . ?
N1 C4 C2 109.06(13) . . ?
N1 C16 C17 111.69(17) . . ?
N1 C16 C18 115.23(16) . . ?
C17 C16 C18 111.12(19) . . ?
N2 C8 C10 109.41(16) . . ?
N2 C8 C9 113.73(16) . . ?
C10 C8 C9 113.63(17) . . ?
N2 C3 C2 109.68(13) . . ?
C30 C2 C1 110.22(12) . . ?
C30 C2 C3 113.27(13) . . ?
C1 C2 C3 102.83(13) . . ?
C30 C2 C4 110.53(13) . . ?
C1 C2 C4 109.74(12) . . ?
C3 C2 C4 109.99(13) . . ?
N2 C7 C6 111.33(13) . . ?
C24 C6 C1 111.29(13) . . ?
C24 C6 C7 112.48(15) . . ?
C1 C6 C7 104.24(13) . . ?
C24 C6 C5 109.41(13) . . ?
C1 C6 C5 108.11(13) . . ?
C7 C6 C5 111.15(14) . . ?
C15 C10 C11 117.8(2) . . ?
C15 C10 C8 120.6(2) . . ?
C11 C10 C8 121.5(2) . . ?
C23 C18 C19 117.9(2) . . ?
C23 C18 C16 119.9(2) . . ?
C19 C18 C16 122.12(17) . . ?
O1 C1 C2 123.25(14) . . ?
O1 C1 C6 123.79(15) . . ?
C2 C1 C6 112.28(12) . . ?
C24 C25 C26 120.1(4) . . ?
C25 C24 C29 118.5(2) . . ?
C25 C24 C6 123.2(2) . . ?
C29 C24 C6 118.2(2) . . ?
C30 C31 C32 121.1(2) . . ?
C33 C34 C35 121.2(2) . . ?
C28 C29 C24 120.7(3) . . ?
C33 C32 C31 120.6(2) . . ?
C10 C11 C12 120.6(3) . . ?
C13 C12 C11 120.7(3) . . ?
C34 C33 C32 118.93(19) . . ?
C30 C35 C34 120.5(2) . . ?
C18 C23 C22 120.2(3) . . ?
C21 C20 C19 120.1(3) . . ?
C20 C19 C18 121.4(2) . . ?
C27 C28 C29 120.4(4) . . ?
C27 C26 C25 120.9(4) . . ?
C10 C15 C14 120.6(3) . . ?
C13 C14 C15 120.7(3) . . ?
C22 C21 C20 119.3(3) . . ?
C12 C13 C14 119.5(3) . . ?
C21 C22 C23 121.1(2) . . ?
C26 C27 C28 119.4(3) . . ?

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_cu_fio4
_database_code_depnum_ccdc_archive 'CCDC 1822007'
_audit_update_record             
;
2018-06-01 deposited with the CCDC.
2018-06-12 downloaded from the CCDC.
;

_vrf_THETM01_ALERT_3_A           
;
PROBLEM:  The value of sine(theta_max)/wavelength is less than 0.550
Calculated sin(theta_max)/wavelength = 0.4694           
RESPONSE: 
           The crystal diffraction at high angles is low due to the low crystal quality 
;
_vrf_REFNR01_ALERT_3_B           
;
PROBLEM:  Ratio of reflections to parameters is < 8 for a centrosymmetric structure
sine(theta)/lambda 0.4694
Proportion of unique data used 1.0000
Ratio reflections to parameters 6.7157
RESPONSE: 
          The crystal diffraction at high angles is low due to the low crystal quality
;
_vrf_PLAT234_ALERT_4_A           
;
PROBLEM:  Large Hirshfeld Difference O3 --C18 0.32 Ang.
RESPONSE: 
          This is due to the single crystal low quality and does not indicate 
an incorrect atom-type assignment
;
_vrf_PLAT234_ALERT_4_B           
; 
PROBLEM:  Large Hirshfeld Difference O3 --C21 0.28 Ang.Large Hirshfeld Difference C2 --C18 0.30 Ang.
RESPONSE: 
          This is due to the single crystal low quality and does not indicate 
an incorrect atom-type assignment
;
_vrf_PLAT241_ALERT_2_B           
;
PROBLEM: High ?MainMol? Ueq as Compared to Neighbors of O3 Check. High ?MainMol? Ueq as Compared to Neighbors of C26 Check
RESPONSE: 
          This is due to the single crystal low quality and does not indicate 
an incorrect atom-type assignment
;
_vrf_PLAT242_ALERT_2_B           
;
PROBLEM: Low ?MainMol? Ueq as Compared to Neighbors of C33 Check
RESPONSE: 
          This is due to the single crystal low quality and does not indicate 
an incorrect atom-type assignment
;
_vrf_PLAT306_ALERT_2_B           
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) ....... Ow1 Check
Isolated Oxygen Atom (H-atoms Missing ?) ....... Ow2 Check
RESPONSE: 
          This is due to disordered water molecules
;
_vrf_PLAT331_ALERT_2_B           
;
PROBLEM: Small Average Phenyl C-C Dist C24 -C33 1.36 Ang.
Small Average Phenyl C-C Dist C24 -C33 1.36 Ang.
RESPONSE: 
          This is due to the single crystal low quality and does not indicate 
an incorrect atom-type assignment
;
_vrf_PLAT341_ALERT_3_B           
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.02532 Ang.
RESPONSE: 
          This is due to the single crystal low quality and does not indicate 
an incorrect atom-type assignment
;
_vrf_PLAT412_ALERT_2_B           
;
PROBLEM: Short Intra XH3 .. XHn H7A ..H23C 1.75 Ang.
Short Intra XH3 .. XHn H23C ..H25 1.74 Ang.
RESPONSE: 
          This is due to the single crystal low quality and does not indicate 
an incorrect atom-type assignment
;
_vrf_PLAT413_ALERT_2_B           
;
PROBLEM: Short Short Inter XH3 .. XHn H23A ..H28 1.98 Ang.
Short Inter XH3 .. XHn H23E ..H24 1.93 Ang.
RESPONSE: 
          This is due to the single crystal low quality and does not indicate 
an incorrect atom-type assignment
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H33 Cl2 Cu N4 O8'
_chemical_formula_weight         712.04

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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                   19.0262(8)
_cell_length_b                   12.6963(8)
_cell_length_c                   13.6195(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.93(2)
_cell_angle_gamma                90
_cell_volume                     3258.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2601
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      20.33

_exptl_crystal_description       laminar
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.889
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.636
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   SADABS
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD diffractometer'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            9148
_diffrn_reflns_av_unetI/netI     0.0951
_diffrn_reflns_av_R_equivalents  0.1085
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.081
_diffrn_reflns_theta_max         19.488
_diffrn_reflns_theta_full        19.488
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2787
_reflns_number_gt                1637
_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       'Apex data collection software'
_computing_cell_refinement       'SAINT software'
_computing_data_reduction        ?
_computing_structure_solution    'SIR-97 for Windows (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_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)+(0.0692P)²+6.8487P] 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         2787
_refine_ls_number_parameters     415
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1445
_refine_ls_R_factor_gt           0.0773
_refine_ls_wR_factor_ref         0.1786
_refine_ls_wR_factor_gt          0.1499
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.002

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 0.3293(8) 0.9276(10) 0.4708(11) 0.081(4) Uani 1 1 d . . . . .
C2 C 0.3141(9) 1.0448(9) 0.4360(12) 0.087(4) Uani 1 1 d . . . . .
C3 C 0.2686(6) 0.9004(7) 0.5335(8) 0.055(3) Uani 1 1 d . . . . .
C4 C 0.2850(6) 0.9672(9) 0.6324(9) 0.068(3) Uani 1 1 d . . . . .
H4 H 0.328932 0.941148 0.670727 0.081 Uiso 1 1 calc R U . . .
C5 C 0.3319(7) 1.1134(9) 0.5314(10) 0.079(4) Uani 1 1 d . . . . .
H5 H 0.382935 1.107760 0.554418 0.095 Uiso 1 1 calc R U . . .
C6 C 0.1976(6) 0.9186(8) 0.4760(8) 0.068(3) Uani 1 1 d . . . . .
H6A H 0.192175 0.873153 0.418267 0.082 Uiso 1 1 calc R U . . .
H6B H 0.161636 0.898965 0.516604 0.082 Uiso 1 1 calc R U . . .
C7 C 0.2399(11) 1.0559(9) 0.3832(9) 0.099(5) Uani 1 1 d . . . . .
H7A H 0.232537 1.128272 0.361496 0.119 Uiso 1 1 calc R U . . .
H7B H 0.234738 1.011628 0.324623 0.119 Uiso 1 1 calc R U . . .
C8 C 0.2251(8) 0.9570(10) 0.6945(9) 0.062(4) Uani 1 1 d . . . . .
C9 C 0.2222(8) 0.8793(10) 0.7648(11) 0.078(4) Uani 1 1 d . . . . .
H9 H 0.258324 0.829707 0.776862 0.094 Uiso 1 1 calc R U . . .
C10 C 0.1641(11) 0.8762(12) 0.8179(10) 0.097(5) Uani 1 1 d . . . . .
H10 H 0.161309 0.823999 0.865098 0.116 Uiso 1 1 calc R U . . .
C11 C 0.1122(8) 0.9488(14) 0.8003(10) 0.094(4) Uani 1 1 d . . . . .
H11 H 0.073284 0.946825 0.834760 0.112 Uiso 1 1 calc R U . . .
C12 C 0.1177(8) 1.0256(11) 0.7310(11) 0.081(4) Uani 1 1 d . . . . .
H12 H 0.081917 1.075728 0.718825 0.097 Uiso 1 1 calc R U . . .
C13 C 0.2265(9) 1.3535(15) 0.5065(9) 0.105(5) Uani 1 1 d . . . . .
H13 H 0.179718 1.370781 0.512207 0.126 Uiso 1 1 calc R U . . .
C14 C 0.2717(14) 1.4308(13) 0.4818(11) 0.123(6) Uani 1 1 d . . . . .
H14 H 0.255754 1.499726 0.472333 0.148 Uiso 1 1 calc R U . . .
C15 C 0.3407(13) 1.4055(16) 0.4713(11) 0.116(6) Uani 1 1 d . . . . .
H15 H 0.371686 1.456746 0.453915 0.139 Uiso 1 1 calc R U . . .
C16 C 0.3632(9) 1.3012(14) 0.4874(10) 0.110(5) Uani 1 1 d . . . . .
H16 H 0.409499 1.281444 0.481523 0.132 Uiso 1 1 calc R U . . .
C17 C 0.3140(11) 1.2274(12) 0.5124(10) 0.086(4) Uani 1 1 d . . . . .
C19 C 0.2735(8) 0.7808(11) 0.5589(9) 0.075(4) Uani 1 1 d . . . . .
C20 C 0.3367(8) 0.6485(10) 0.6527(9) 0.126(6) Uani 1 1 d . . . . .
H20A H 0.376302 0.640315 0.704062 0.190 Uiso 1 1 calc R U . . .
H20B H 0.294680 0.621043 0.675212 0.190 Uiso 1 1 calc R U . . .
H20C H 0.345767 0.610713 0.594724 0.190 Uiso 1 1 calc R U . . .
C22 C 0.1096(8) 1.0414(10) 0.3874(10) 0.102(5) Uani 1 1 d . . . . .
C23A C 0.1143(19) 1.162(2) 0.3380(19) 0.155(15) Uani 0.5 1 d . . P . .
H23A H 0.069363 1.179436 0.300649 0.233 Uiso 0.5 1 calc R U P . .
H23B H 0.125976 1.212321 0.390130 0.233 Uiso 0.5 1 calc R U P . .
H23C H 0.150323 1.162340 0.295104 0.233 Uiso 0.5 1 calc R U P . .
C23B C 0.0449(12) 0.9943(18) 0.4603(16) 0.087(8) Uani 0.5 1 d . . P . .
H23D H -0.001759 1.003531 0.424180 0.131 Uiso 0.5 1 calc R U P . .
H23E H 0.052932 0.920841 0.474475 0.131 Uiso 0.5 1 calc R U P . .
H23F H 0.048617 1.033078 0.521249 0.131 Uiso 0.5 1 calc R U P . .
C34 C 0.3273(6) 1.1310(9) 0.7085(9) 0.091(4) Uani 1 1 d . . . . .
H34A H 0.332411 1.205233 0.698209 0.136 Uiso 1 1 calc R U . . .
H34B H 0.298709 1.119696 0.760392 0.136 Uiso 1 1 calc R U . . .
H34C H 0.373262 1.100055 0.727079 0.136 Uiso 1 1 calc R U . . .
N1 N 0.1855(7) 1.0276(8) 0.4434(7) 0.084(3) Uani 1 1 d . . . . .
N2 N 0.2923(5) 1.0810(7) 0.6148(7) 0.067(3) Uani 1 1 d . . . . .
N3 N 0.2481(9) 1.2550(9) 0.5222(7) 0.088(4) Uani 1 1 d . . . . .
N4 N 0.1746(6) 1.0306(7) 0.6790(6) 0.059(3) Uani 1 1 d . . . . .
O1 O 0.3948(5) 0.9152(7) 0.5262(7) 0.107(3) Uani 1 1 d . . . . .
H1 H 0.425795 0.929303 0.492028 0.161 Uiso 1 1 calc R U . . .
O2 O 0.3213(4) 0.8654(6) 0.3831(6) 0.092(3) Uani 1 1 d . . . . .
H2 H 0.324376 0.802859 0.398089 0.138 Uiso 1 1 calc R U . . .
O5 O 0.2352(6) 0.7161(7) 0.5171(7) 0.112(4) Uani 1 1 d . . . . .
O6 O 0.3266(5) 0.7600(6) 0.6288(6) 0.089(3) Uani 1 1 d . . . . .
OW1 O 0.4954(6) 0.8515(9) 0.3542(11) 0.191(5) Uani 1 1 d . . . . .
OW2 O 0.5043(7) 0.9207(12) 0.1265(13) 0.235(7) Uani 1 1 d . . . . .
Cl1 Cl 0.09121(19) 1.2306(2) 0.5786(3) 0.0966(12) Uani 1 1 d . . . . .
Cl2 Cl 0.4134(2) 0.6537(3) 0.3954(4) 0.1465(17) Uani 1 1 d . . . . .
Cu1 Cu 0.19332(8) 1.14218(10) 0.58170(10) 0.0740(6) Uani 1 1 d . . . . .
O3 O 0.4271(12) 1.077(2) 0.391(2) 0.256(14) Uani 1 1 d . . . . .
O4 O 0.3360(8) 1.1007(9) 0.2761(11) 0.164(5) Uani 1 1 d D . . . .
C21 C 0.4637(10) 1.1214(14) 0.2973(15) 0.209(11) Uani 1 1 d . . . . .
H21A H 0.514337 1.122734 0.314674 0.314 Uiso 1 1 calc R U . . .
H21B H 0.451375 1.076066 0.241163 0.314 Uiso 1 1 calc R U . . .
H21C H 0.446834 1.191389 0.280936 0.314 Uiso 1 1 calc R U . . .
C18 C 0.3758(18) 1.0770(17) 0.3711(16) 0.178(16) Uani 1 1 d D . . . .
C33 C 0.0959(8) 0.9710(13) 0.2928(10) 0.090(4) Uani 1 1 d . . . . .
C24 C 0.0657(8) 0.8742(17) 0.2926(14) 0.104(5) Uani 1 1 d . . . . .
H24 H 0.057704 0.844735 0.352582 0.125 Uiso 1 1 calc R U . . .
C28 C 0.0462(12) 0.8173(16) 0.205(2) 0.167(11) Uani 1 1 d . . . . .
H28 H 0.023202 0.752786 0.205805 0.200 Uiso 1 1 calc R U . . .
C25 C 0.1096(12) 1.0072(17) 0.2029(16) 0.227(13) Uani 1 1 d . . . . .
H25 H 0.130524 1.073032 0.198802 0.272 Uiso 1 1 calc R U . . .
C27 C 0.0621(13) 0.860(3) 0.120(2) 0.185(13) Uani 1 1 d . . . . .
H27 H 0.050359 0.823676 0.060440 0.222 Uiso 1 1 calc R U . . .
C26 C 0.0935(14) 0.949(2) 0.1207(16) 0.28(2) Uani 1 1 d . . . . .
H26 H 0.105523 0.975382 0.061409 0.330 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
C1 O1 1.374(14) . ?
C1 O2 1.422(13) . ?
C1 C3 1.565(16) . ?
C1 C2 1.577(17) . ?
C2 C7 1.500(17) . ?
C2 C5 1.562(16) . ?
C2 C18 1.62(3) . ?
C3 C6 1.483(14) . ?
C3 C19 1.557(15) . ?
C3 C4 1.586(14) . ?
C4 N2 1.474(13) . ?
C4 C8 1.516(15) . ?
C5 C17 1.501(17) . ?
C5 N2 1.505(14) . ?
C6 N1 1.461(13) . ?
C7 N1 1.452(16) . ?
C8 N4 1.336(13) . ?
C8 C9 1.381(15) . ?
C9 C10 1.402(17) . ?
C10 C11 1.347(17) . ?
C11 C12 1.372(16) . ?
C12 N4 1.374(14) . ?
C13 N3 1.324(16) . ?
C13 C14 1.377(19) . ?
C14 C15 1.38(2) . ?
C15 C16 1.40(2) . ?
C16 C17 1.399(18) . ?
C17 N3 1.327(15) . ?
C19 O5 1.190(14) . ?
C19 O6 1.316(12) . ?
C20 O6 1.460(13) . ?
C22 N1 1.547(15) . ?
C22 C33 1.560(17) . ?
C22 C23A 1.68(3) . ?
C22 C23B 1.79(2) . ?
C34 N2 1.497(12) . ?
N1 Cu1 2.368(9) . ?
N2 Cu1 2.029(9) . ?
N3 Cu1 2.007(10) . ?
N4 Cu1 2.005(9) . ?
Cl1 Cu1 2.239(4) . ?
O3 C18 0.98(4) . ?
O3 C21 1.64(3) . ?
O4 C18 1.438(19) . ?
C33 C24 1.356(18) . ?
C33 C25 1.366(19) . ?
C24 C28 1.40(2) . ?
C28 C27 1.35(3) . ?
C25 C26 1.34(2) . ?
C27 C26 1.29(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
O1 C1 O2 112.4(11) . . ?
O1 C1 C3 110.9(11) . . ?
O2 C1 C3 109.5(10) . . ?
O1 C1 C2 112.8(12) . . ?
O2 C1 C2 106.1(11) . . ?
C3 C1 C2 104.8(11) . . ?
C7 C2 C5 115.3(12) . . ?
C7 C2 C1 110.7(11) . . ?
C5 C2 C1 105.4(12) . . ?
C7 C2 C18 114.9(16) . . ?
C5 C2 C18 102.9(13) . . ?
C1 C2 C18 106.7(13) . . ?
C6 C3 C19 106.9(10) . . ?
C6 C3 C1 111.4(10) . . ?
C19 C3 C1 108.1(10) . . ?
C6 C3 C4 115.0(9) . . ?
C19 C3 C4 109.5(9) . . ?
C1 C3 C4 105.8(10) . . ?
N2 C4 C8 105.6(9) . . ?
N2 C4 C3 113.5(9) . . ?
C8 C4 C3 110.7(9) . . ?
C17 C5 N2 105.5(11) . . ?
C17 C5 C2 112.1(11) . . ?
N2 C5 C2 113.7(10) . . ?
N1 C6 C3 113.7(10) . . ?
N1 C7 C2 113.8(12) . . ?
N4 C8 C9 120.8(13) . . ?
N4 C8 C4 115.6(11) . . ?
C9 C8 C4 123.6(14) . . ?
C8 C9 C10 119.1(12) . . ?
C11 C10 C9 120.0(14) . . ?
C10 C11 C12 119.0(14) . . ?
C11 C12 N4 121.9(12) . . ?
N3 C13 C14 121.4(16) . . ?
C13 C14 C15 119.8(17) . . ?
C14 C15 C16 118.6(17) . . ?
C17 C16 C15 118.1(16) . . ?
N3 C17 C16 121.4(14) . . ?
N3 C17 C5 115.7(15) . . ?
C16 C17 C5 123.0(17) . . ?
O5 C19 O6 124.5(12) . . ?
O5 C19 C3 123.6(11) . . ?
O6 C19 C3 111.9(12) . . ?
N1 C22 C33 112.4(10) . . ?
N1 C22 C23A 101.8(15) . . ?
C33 C22 C23A 101.8(13) . . ?
N1 C22 C23B 110.8(12) . . ?
C33 C22 C23B 102.5(13) . . ?
C23A C22 C23B 127.3(16) . . ?
C7 N1 C6 108.1(10) . . ?
C7 N1 C22 112.5(12) . . ?
C6 N1 C22 110.8(11) . . ?
C7 N1 Cu1 109.0(8) . . ?
C6 N1 Cu1 110.5(7) . . ?
C22 N1 Cu1 106.0(7) . . ?
C4 N2 C34 108.5(8) . . ?
C4 N2 C5 117.3(9) . . ?
C34 N2 C5 108.5(9) . . ?
C4 N2 Cu1 107.8(7) . . ?
C34 N2 Cu1 108.5(7) . . ?
C5 N2 Cu1 105.9(7) . . ?
C13 N3 C17 120.7(14) . . ?
C13 N3 Cu1 124.9(15) . . ?
C17 N3 Cu1 113.7(11) . . ?
C8 N4 C12 119.1(10) . . ?
C8 N4 Cu1 114.2(10) . . ?
C12 N4 Cu1 126.7(10) . . ?
C19 O6 C20 114.9(10) . . ?
N4 Cu1 N3 157.0(5) . . ?
N4 Cu1 N2 80.0(4) . . ?
N3 Cu1 N2 81.1(6) . . ?
N4 Cu1 Cl1 97.7(4) . . ?
N3 Cu1 Cl1 97.6(5) . . ?
N2 Cu1 Cl1 166.5(3) . . ?
N4 Cu1 N1 95.4(4) . . ?
N3 Cu1 N1 95.6(5) . . ?
N2 Cu1 N1 84.0(4) . . ?
Cl1 Cu1 N1 109.5(3) . . ?
C18 O3 C21 107(3) . . ?
O3 C18 O4 129(3) . . ?
O3 C18 C2 128(3) . . ?
O4 C18 C2 102(2) . . ?
C24 C33 C25 115.9(14) . . ?
C24 C33 C22 122.9(18) . . ?
C25 C33 C22 121.0(18) . . ?
C33 C24 C28 122.2(17) . . ?
C27 C28 C24 118(2) . . ?
C26 C25 C33 120.9(17) . . ?
C26 C27 C28 120(3) . . ?
C27 C26 C25 123(2) . . ?

_refine_diff_density_max         0.326
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.060

