# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_pa102a
_database_code_depnum_ccdc_archive 'CCDC 2208156'
loop_
_audit_author_name
_audit_author_address
'Rahman Bikas'
;Imam khomeini International University, Qazvin
Iran
;
_audit_update_record             
;
2022-09-19 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 Cu N4 O7, C H4 O'
_chemical_formula_sum            'C17 H22 Cu N4 O8'
_chemical_formula_weight         473.92

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'
Cu Cu 0.3201 1.2651 '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                   7.814(2)
_cell_length_b                   11.098(3)
_cell_length_c                   12.616(4)
_cell_angle_alpha                98.42(5)
_cell_angle_beta                 105.98(5)
_cell_angle_gamma                107.55(5)
_cell_volume                     970.9(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4766
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_F_000             490
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.180
_shelx_estimated_absorpt_T_min   0.563
_shelx_estimated_absorpt_T_max   0.891
_exptl_absorpt_correction_T_min  0.591
_exptl_absorpt_correction_T_max  0.897
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_measurement_device_type  
;
Kuma KM4 kappa-geometry diffractometer with a CCD detector
;
_diffrn_measurement_method       w/
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9665
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.835
_diffrn_reflns_theta_max         27.997
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4428
_reflns_number_gt                3888
_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       'CrysAlis CCD; Oxford-Diffraction Poland, 2003'
_computing_cell_refinement       'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_data_reduction        'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.1000P)²+0.6156P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4428
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1583
_refine_ls_wR_factor_gt          0.1481
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
Cu Cu 0.35309(5) 0.71185(3) 0.60657(3) 0.01905(15) Uani 1 1 d . . . . .
O2 O 0.4530(3) 0.60388(19) 0.68879(18) 0.0205(4) Uani 1 1 d . . . . .
C1 C 0.3222(4) 0.4073(3) 0.5349(2) 0.0172(5) Uani 1 1 d . . . . .
C2 C 0.4339(4) 0.4821(3) 0.6470(3) 0.0185(6) Uani 1 1 d . . . . .
C3 C 0.3171(4) 0.2783(3) 0.4987(3) 0.0202(6) Uani 1 1 d . . . . .
H3 H 0.2431 0.2290 0.4227 0.024 Uiso 1 1 calc R U . . .
C4 C 0.4180(5) 0.2244(3) 0.5721(3) 0.0226(6) Uani 1 1 d . . . . .
H4 H 0.4143 0.1384 0.5467 0.027 Uiso 1 1 calc R U . . .
C5 C 0.5262(4) 0.2958(3) 0.6843(3) 0.0206(6) Uani 1 1 d . . . . .
H5 H 0.5948 0.2580 0.7353 0.025 Uiso 1 1 calc R U . . .
C6 C 0.5334(4) 0.4215(3) 0.7210(3) 0.0197(6) Uani 1 1 d . . . . .
O6 O 0.6327(3) 0.4988(2) 0.82903(18) 0.0246(5) Uani 1 1 d . . . . .
C7 C 0.2100(4) 0.4546(3) 0.4529(2) 0.0185(5) Uani 1 1 d . . . . .
H7 H 0.1391 0.3990 0.3788 0.022 Uiso 1 1 calc R U . . .
N1 N 0.2008(4) 0.5699(2) 0.4752(2) 0.0187(5) Uani 1 1 d . . . . .
N2 N 0.0868(4) 0.6068(2) 0.3918(2) 0.0185(5) Uani 1 1 d . . . . .
H2 H 0.0072 0.5517 0.3269 0.066(16) Uiso 1 1 calc R . . . .
C8 C 0.1065(4) 0.7338(3) 0.4169(2) 0.0186(6) Uani 1 1 d . . . . .
O1 O 0.2225(3) 0.80623(19) 0.51330(17) 0.0198(4) Uani 1 1 d . . . . .
C11 C -0.0025(4) 0.7848(3) 0.3338(2) 0.0180(5) Uani 1 1 d . . . . .
C21 C -0.1202(4) 0.7101(3) 0.2238(3) 0.0207(6) Uani 1 1 d . . . . .
H21 H -0.1322 0.6216 0.2015 0.025 Uiso 1 1 calc R U . . .
C31 C -0.2191(4) 0.7630(3) 0.1472(2) 0.0205(6) Uani 1 1 d . . . . .
H31 H -0.2978 0.7105 0.0729 0.025 Uiso 1 1 calc R U . . .
C41 C -0.2047(4) 0.8943(3) 0.1779(2) 0.0183(6) Uani 1 1 d . . . . .
C51 C -0.0885(4) 0.9695(3) 0.2893(3) 0.0199(6) Uani 1 1 d . . . . .
H51 H -0.0787 1.0574 0.3123 0.024 Uiso 1 1 calc R U . . .
C61 C 0.0106(4) 0.9159(3) 0.3646(2) 0.0191(6) Uani 1 1 d . . . . .
H61 H 0.0894 0.9681 0.4390 0.023 Uiso 1 1 calc R U . . .
N3 N -0.3035(4) 0.9451(2) 0.1025(2) 0.0231(5) Uani 1 1 d . . . . .
H3A H -0.3628 0.8921 0.0308 0.048(13) Uiso 1 1 d R . . . .
H3B H -0.2985 1.0292 0.1153 0.050(13) Uiso 1 1 d R . . . .
C9 C 0.7348(5) 0.4448(3) 0.9096(3) 0.0287(7) Uani 1 1 d . . . . .
H9A H 0.6455 0.3656 0.9173 0.043 Uiso 1 1 calc R U . . .
H9B H 0.7977 0.5088 0.9836 0.043 Uiso 1 1 calc R U . . .
H9C H 0.8310 0.4230 0.8830 0.043 Uiso 1 1 calc R U . . .
O3 O 0.1799(3) 0.7414(2) 0.73000(18) 0.0236(5) Uani 1 1 d . . . . .
N4 N 0.2074(4) 0.7026(2) 0.8210(2) 0.0197(5) Uani 1 1 d . . . . .
O4 O 0.1211(3) 0.5861(2) 0.81756(19) 0.0263(5) Uani 1 1 d . . . . .
O5 O 0.3145(3) 0.7810(2) 0.9132(2) 0.0288(5) Uani 1 1 d . . . . .
O1M O 0.5694(3) 0.86483(19) 0.70890(18) 0.0218(4) Uani 1 1 d . . . . .
H1M H 0.6038 0.8393 0.7680 0.042(12) Uiso 1 1 d R . . . .
C1M C 0.5781(5) 0.9980(3) 0.7299(3) 0.0293(7) Uani 1 1 d . . . . .
H1M1 H 0.6651 1.0482 0.6958 0.044 Uiso 1 1 calc R U . . .
H1M2 H 0.6246 1.0363 0.8122 0.044 Uiso 1 1 calc R U . . .
H1M3 H 0.4505 1.0002 0.6960 0.044 Uiso 1 1 calc R U . . .
O2M O 0.7080(3) 0.7820(2) 0.88392(17) 0.0231(4) Uani 1 1 d . . . . .
H2M H 0.6484 0.7014 0.8702 0.072(18) Uiso 1 1 d R . . . .
C2M C 0.9074(5) 0.8063(3) 0.9089(3) 0.0293(7) Uani 1 1 d . . . . .
H2M1 H 0.9816 0.8923 0.9619 0.044 Uiso 1 1 calc R U . . .
H2M2 H 0.9374 0.8042 0.8383 0.044 Uiso 1 1 calc R U . . .
H2M3 H 0.9398 0.7390 0.9435 0.044 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
Cu O2 1.898(2) . ?
Cu N1 1.914(3) . ?
Cu O1M 1.958(3) . ?
Cu O1 1.966(2) . ?
Cu O3 2.375(2) . ?
O2 C2 1.324(3) . ?
C1 C2 1.411(4) . ?
C1 C3 1.422(4) . ?
C1 C7 1.432(4) . ?
C2 C6 1.424(4) . ?
C3 C4 1.372(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(4) . ?
C5 H5 0.9500 . ?
C6 O6 1.367(4) . ?
O6 C9 1.431(4) . ?
C7 N1 1.298(4) . ?
C7 H7 0.9500 . ?
N1 N2 1.378(4) . ?
N2 C8 1.350(4) . ?
N2 H2 0.8800 . ?
C8 O1 1.271(4) . ?
C8 C11 1.455(4) . ?
C11 C21 1.400(4) . ?
C11 C61 1.415(4) . ?
C21 C31 1.379(4) . ?
C21 H21 0.9500 . ?
C31 C41 1.414(4) . ?
C31 H31 0.9500 . ?
C41 N3 1.354(4) . ?
C41 C51 1.411(4) . ?
C51 C61 1.376(4) . ?
C51 H51 0.9500 . ?
C61 H61 0.9500 . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
O3 N4 1.270(3) . ?
N4 O5 1.241(4) . ?
N4 O4 1.254(3) . ?
O1M C1M 1.440(3) . ?
O1M H1M 0.8400 . ?
C1M H1M1 0.9800 . ?
C1M H1M2 0.9800 . ?
C1M H1M3 0.9800 . ?
O2M C2M 1.433(4) . ?
O2M H2M 0.8400 . ?
C2M H2M1 0.9800 . ?
C2M H2M2 0.9800 . ?
C2M H2M3 0.9800 . ?

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
O2 Cu N1 92.77(10) . . ?
O2 Cu O1M 89.32(10) . . ?
N1 Cu O1M 159.51(10) . . ?
O2 Cu O1 173.46(9) . . ?
N1 Cu O1 81.79(10) . . ?
O1M Cu O1 97.05(10) . . ?
O2 Cu O3 91.59(9) . . ?
N1 Cu O3 111.68(10) . . ?
O1M Cu O3 88.61(9) . . ?
O1 Cu O3 87.10(8) . . ?
C2 O2 Cu 126.3(2) . . ?
C2 C1 C3 120.0(3) . . ?
C2 C1 C7 123.1(3) . . ?
C3 C1 C7 116.9(3) . . ?
O2 C2 C1 125.2(3) . . ?
O2 C2 C6 117.5(3) . . ?
C1 C2 C6 117.3(3) . . ?
C4 C3 C1 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C1 C3 H3 119.6 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
O6 C6 C5 124.6(3) . . ?
O6 C6 C2 113.6(2) . . ?
C5 C6 C2 121.7(3) . . ?
C6 O6 C9 117.3(2) . . ?
N1 C7 C1 123.1(3) . . ?
N1 C7 H7 118.5 . . ?
C1 C7 H7 118.5 . . ?
C7 N1 N2 119.2(3) . . ?
C7 N1 Cu 128.2(2) . . ?
N2 N1 Cu 112.03(18) . . ?
C8 N2 N1 115.0(2) . . ?
C8 N2 H2 122.5 . . ?
N1 N2 H2 122.5 . . ?
O1 C8 N2 118.4(3) . . ?
O1 C8 C11 121.7(3) . . ?
N2 C8 C11 119.9(3) . . ?
C8 O1 Cu 112.77(18) . . ?
C21 C11 C61 118.0(3) . . ?
C21 C11 C8 123.0(3) . . ?
C61 C11 C8 118.9(3) . . ?
C31 C21 C11 121.1(3) . . ?
C31 C21 H21 119.5 . . ?
C11 C21 H21 119.5 . . ?
C21 C31 C41 120.8(3) . . ?
C21 C31 H31 119.6 . . ?
C41 C31 H31 119.6 . . ?
N3 C41 C51 121.2(3) . . ?
N3 C41 C31 120.4(3) . . ?
C51 C41 C31 118.3(3) . . ?
C61 C51 C41 120.3(3) . . ?
C61 C51 H51 119.9 . . ?
C41 C51 H51 119.9 . . ?
C51 C61 C11 121.4(3) . . ?
C51 C61 H61 119.3 . . ?
C11 C61 H61 119.3 . . ?
C41 N3 H3A 114.3 . . ?
C41 N3 H3B 125.4 . . ?
H3A N3 H3B 119.5 . . ?
O6 C9 H9A 109.5 . . ?
O6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 O3 Cu 120.66(17) . . ?
O5 N4 O4 120.3(3) . . ?
O5 N4 O3 120.0(2) . . ?
O4 N4 O3 119.7(3) . . ?
C1M O1M Cu 126.7(2) . . ?
C1M O1M H1M 114.5 . . ?
Cu O1M H1M 102.9 . . ?
O1M C1M H1M1 109.5 . . ?
O1M C1M H1M2 109.5 . . ?
H1M1 C1M H1M2 109.5 . . ?
O1M C1M H1M3 109.5 . . ?
H1M1 C1M H1M3 109.5 . . ?
H1M2 C1M H1M3 109.5 . . ?
C2M O2M H2M 109.5 . . ?
O2M C2M H2M1 109.5 . . ?
O2M C2M H2M2 109.5 . . ?
H2M1 C2M H2M2 109.5 . . ?
O2M C2M H2M3 109.5 . . ?
H2M1 C2M H2M3 109.5 . . ?
H2M2 C2M H2M3 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 O3 0.95 2.38 3.163(5) 139.2 2_566
N2 H2 O4 0.88 1.98 2.843(4) 166.5 2_566
N3 H3A O5 0.91 2.37 3.075(5) 134.4 1_454
N3 H3A O2M 0.91 2.35 3.109(4) 140.2 1_454
N3 H3B O5 0.91 2.22 3.100(3) 161.8 2_576
O1M H1M O2M 0.84 1.77 2.602(3) 170.1 .
O2M H2M O2 0.84 2.26 2.727(4) 115.5 .
O2M H2M O6 0.84 2.19 2.953(3) 151.1 .

_refine_diff_density_max         0.832
_refine_diff_density_min         -1.191
_refine_diff_density_rms         0.129

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_ftcat63
_database_code_depnum_ccdc_archive 'CCDC 2208157'
loop_
_audit_author_name
_audit_author_address
'Rahman Bikas'
;Imam khomeini International University, Qazvin
Iran
;
_audit_update_record             
;
2022-09-19 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H22 O2'
_chemical_formula_sum            'C16 H22 O2'
_chemical_formula_weight         246.33

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'
O O 0.0106 0.0060 '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                   11.608(3)
_cell_length_b                   17.840(4)
_cell_length_c                   11.947(3)
_cell_angle_alpha                90
_cell_angle_beta                 118.47(4)
_cell_angle_gamma                90
_cell_volume                     2174.9(12)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(3)
_cell_measurement_reflns_used    12124
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_F_000             804
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_measurement_device_type  
;
Kuma KM4 kappa-geometry diffractometer with a CCD detector
;
_diffrn_measurement_method       /w
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25001
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.996
_diffrn_reflns_theta_max         29.000
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5697
_reflns_number_gt                4729
_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       'CrysAlisCCD (Oxford Diffraction, 2003)'
_computing_cell_refinement       'CrysAlisRED (Oxford Diffraction, 2007)'
_computing_data_reduction        CrysAlisRED
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0819P)²+0.4931P]
 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         5697
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1475
_refine_ls_wR_factor_gt          0.1362
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
O1A O 0.45397(8) 0.87881(5) 1.05354(8) 0.01814(19) Uani 1 1 d . . . . .
H1A H 0.4222 0.8916 0.9768 0.027 Uiso 1 1 calc R U . . .
C1A C 0.56925(11) 0.83371(6) 1.08866(11) 0.0142(2) Uani 1 1 d . . . . .
C2A C 0.62837(12) 0.81787(7) 1.23189(11) 0.0188(2) Uani 1 1 d . . . . .
H2A1 H 0.6429 0.8659 1.2783 0.023 Uiso 1 1 calc R U . . .
H2A2 H 0.5657 0.7878 1.2474 0.023 Uiso 1 1 calc R U . . .
C3A C 0.75821(12) 0.77563(7) 1.28306(12) 0.0231(3) Uani 1 1 d . . . . .
H3A1 H 0.7424 0.7254 1.2431 0.028 Uiso 1 1 calc R U . . .
H3A2 H 0.7957 0.7687 1.3761 0.028 Uiso 1 1 calc R U . . .
C4A C 0.85587(13) 0.81837(8) 1.25531(14) 0.0269(3) Uani 1 1 d . . . . .
H4A1 H 0.9373 0.7887 1.2854 0.032 Uiso 1 1 calc R U . . .
H4A2 H 0.8784 0.8665 1.3022 0.032 Uiso 1 1 calc R U . . .
C5A C 0.79826(12) 0.83360(8) 1.11257(13) 0.0231(3) Uani 1 1 d . . . . .
H5A1 H 0.7837 0.7854 1.0666 0.028 Uiso 1 1 calc R U . . .
H5A2 H 0.8613 0.8634 1.0972 0.028 Uiso 1 1 calc R U . . .
C6A C 0.66832(12) 0.87617(7) 1.06122(12) 0.0193(2) Uani 1 1 d . . . . .
H6A1 H 0.6311 0.8832 0.9682 0.023 Uiso 1 1 calc R U . . .
H6A2 H 0.6845 0.9264 1.1012 0.023 Uiso 1 1 calc R U . . .
C7A C 0.52872(11) 0.76277(6) 1.01601(11) 0.0148(2) Uani 1 1 d . . . . .
C8A C 0.48979(11) 0.70548(6) 0.95538(11) 0.0156(2) Uani 1 1 d . . . . .
C8B C 0.44229(11) 0.64109(6) 0.88450(11) 0.0158(2) Uani 1 1 d . . . . .
C9B C 0.40212(11) 0.58497(6) 0.82151(11) 0.0153(2) Uani 1 1 d . . . . .
O1B O 0.45326(8) 0.50335(4) 0.69558(8) 0.01649(19) Uani 1 1 d . . . . .
H1B H 0.4565 0.5406 0.6541 0.055(6) Uiso 1 1 calc R . . . .
C1B C 0.35995(11) 0.51733(6) 0.73961(11) 0.0147(2) Uani 1 1 d . . . . .
C2B C 0.22286(12) 0.52931(7) 0.62564(12) 0.0203(2) Uani 1 1 d . . . . .
H2B1 H 0.2229 0.5756 0.5800 0.024 Uiso 1 1 calc R U . . .
H2B2 H 0.2013 0.4867 0.5658 0.024 Uiso 1 1 calc R U . . .
C3B C 0.11833(13) 0.53568(9) 0.66865(15) 0.0313(3) Uani 1 1 d . . . . .
H3B1 H 0.1355 0.5807 0.7227 0.038 Uiso 1 1 calc R U . . .
H3B2 H 0.0310 0.5415 0.5932 0.038 Uiso 1 1 calc R U . . .
C4B C 0.11867(16) 0.46614(9) 0.74362(18) 0.0378(4) Uani 1 1 d . . . . .
H4B1 H 0.0537 0.4726 0.7743 0.045 Uiso 1 1 calc R U . . .
H4B2 H 0.0927 0.4218 0.6869 0.045 Uiso 1 1 calc R U . . .
C5B C 0.25401(16) 0.45286(8) 0.85710(16) 0.0313(3) Uani 1 1 d . . . . .
H5B1 H 0.2530 0.4056 0.9001 0.038 Uiso 1 1 calc R U . . .
H5B2 H 0.2751 0.4943 0.9190 0.038 Uiso 1 1 calc R U . . .
C6B C 0.35989(13) 0.44813(7) 0.81590(13) 0.0212(3) Uani 1 1 d . . . . .
H6B1 H 0.3452 0.4027 0.7631 0.025 Uiso 1 1 calc R U . . .
H6B2 H 0.4467 0.4433 0.8924 0.025 Uiso 1 1 calc R U . . .
O1C O 0.65598(8) 0.42658(5) 0.69379(8) 0.01782(19) Uani 1 1 d . . . . .
H1C H 0.6025 0.4474 0.7124 0.041(5) Uiso 1 1 calc R . . . .
C1C C 0.75303(10) 0.38726(6) 0.80317(11) 0.0146(2) Uani 1 1 d . . . . .
C2C C 0.81337(12) 0.32786(7) 0.75373(13) 0.0235(3) Uani 1 1 d . . . . .
H2C1 H 0.7427 0.2963 0.6894 0.028 Uiso 1 1 calc R U . . .
H2C2 H 0.8586 0.3531 0.7118 0.028 Uiso 1 1 calc R U . . .
C3C C 0.91123(13) 0.27795(8) 0.86154(15) 0.0305(3) Uani 1 1 d . . . . .
H3C1 H 0.9436 0.2383 0.8255 0.037 Uiso 1 1 calc R U . . .
H3C2 H 0.9873 0.3085 0.9207 0.037 Uiso 1 1 calc R U . . .
C4C C 0.84825(15) 0.24180(8) 0.93458(17) 0.0357(4) Uani 1 1 d . . . . .
H4C1 H 0.7794 0.2064 0.8780 0.043 Uiso 1 1 calc R U . . .
H4C2 H 0.9153 0.2130 1.0073 0.043 Uiso 1 1 calc R U . . .
C5C C 0.78792(13) 0.30019(8) 0.98389(14) 0.0288(3) Uani 1 1 d . . . . .
H5C1 H 0.8581 0.3321 1.0481 0.035 Uiso 1 1 calc R U . . .
H5C2 H 0.7429 0.2747 1.0258 0.035 Uiso 1 1 calc R U . . .
C6C C 0.68984(11) 0.34934(7) 0.87553(13) 0.0208(3) Uani 1 1 d . . . . .
H6C1 H 0.6553 0.3882 0.9108 0.025 Uiso 1 1 calc R U . . .
H6C2 H 0.6152 0.3181 0.8158 0.025 Uiso 1 1 calc R U . . .
C7C C 0.85676(12) 0.43985(6) 0.88760(12) 0.0180(2) Uani 1 1 d . . . . .
C8C C 0.94778(12) 0.47801(7) 0.95917(12) 0.0204(3) 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
O1A C1A 1.4418(13) . ?
O1A H1A 0.8400 . ?
C1A C7A 1.4788(16) . ?
C1A C2A 1.5360(17) . ?
C1A C6A 1.5373(16) . ?
C2A C3A 1.5280(17) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C3A C4A 1.5279(19) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C4A C5A 1.530(2) . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?
C5A C6A 1.5317(18) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
C7A C8A 1.2089(17) . ?
C8A C8B 1.3769(16) . ?
C8B C9B 1.2047(17) . ?
C9B C1B 1.4821(16) . ?
O1B C1B 1.4336(13) . ?
O1B H1B 0.8400 . ?
C1B C6B 1.5347(16) . ?
C1B C2B 1.5383(19) . ?
C2B C3B 1.5308(19) . ?
C2B H2B1 0.9900 . ?
C2B H2B2 0.9900 . ?
C3B C4B 1.529(2) . ?
C3B H3B1 0.9900 . ?
C3B H3B2 0.9900 . ?
C4B C5B 1.527(3) . ?
C4B H4B1 0.9900 . ?
C4B H4B2 0.9900 . ?
C5B C6B 1.5287(18) . ?
C5B H5B1 0.9900 . ?
C5B H5B2 0.9900 . ?
C6B H6B1 0.9900 . ?
C6B H6B2 0.9900 . ?
O1C C1C 1.4371(15) . ?
O1C H1C 0.8400 . ?
C1C C7C 1.4797(17) . ?
C1C C6C 1.5322(16) . ?
C1C C2C 1.5353(16) . ?
C2C C3C 1.532(2) . ?
C2C H2C1 0.9900 . ?
C2C H2C2 0.9900 . ?
C3C C4C 1.523(2) . ?
C3C H3C1 0.9900 . ?
C3C H3C2 0.9900 . ?
C4C C5C 1.522(2) . ?
C4C H4C1 0.9900 . ?
C4C H4C2 0.9900 . ?
C5C C6C 1.5283(19) . ?
C5C H5C1 0.9900 . ?
C5C H5C2 0.9900 . ?
C6C H6C1 0.9900 . ?
C6C H6C2 0.9900 . ?
C7C C8C 1.2040(18) . ?
C8C C8C 1.382(3) 3_767 ?

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
C1A O1A H1A 109.5 . . ?
O1A C1A C7A 108.38(9) . . ?
O1A C1A C2A 106.66(9) . . ?
C7A C1A C2A 110.16(10) . . ?
O1A C1A C6A 110.35(9) . . ?
C7A C1A C6A 110.95(9) . . ?
C2A C1A C6A 110.23(10) . . ?
C3A C2A C1A 111.60(10) . . ?
C3A C2A H2A1 109.3 . . ?
C1A C2A H2A1 109.3 . . ?
C3A C2A H2A2 109.3 . . ?
C1A C2A H2A2 109.3 . . ?
H2A1 C2A H2A2 108.0 . . ?
C2A C3A C4A 111.07(11) . . ?
C2A C3A H3A1 109.4 . . ?
C4A C3A H3A1 109.4 . . ?
C2A C3A H3A2 109.4 . . ?
C4A C3A H3A2 109.4 . . ?
H3A1 C3A H3A2 108.0 . . ?
C3A C4A C5A 110.80(11) . . ?
C3A C4A H4A1 109.5 . . ?
C5A C4A H4A1 109.5 . . ?
C3A C4A H4A2 109.5 . . ?
C5A C4A H4A2 109.5 . . ?
H4A1 C4A H4A2 108.1 . . ?
C4A C5A C6A 110.99(11) . . ?
C4A C5A H5A1 109.4 . . ?
C6A C5A H5A1 109.4 . . ?
C4A C5A H5A2 109.4 . . ?
C6A C5A H5A2 109.4 . . ?
H5A1 C5A H5A2 108.0 . . ?
C5A C6A C1A 111.35(10) . . ?
C5A C6A H6A1 109.4 . . ?
C1A C6A H6A1 109.4 . . ?
C5A C6A H6A2 109.4 . . ?
C1A C6A H6A2 109.4 . . ?
H6A1 C6A H6A2 108.0 . . ?
C8A C7A C1A 177.02(11) . . ?
C7A C8A C8B 178.51(13) . . ?
C9B C8B C8A 178.85(12) . . ?
C8B C9B C1B 175.31(11) . . ?
C1B O1B H1B 109.5 . . ?
O1B C1B C9B 108.32(9) . . ?
O1B C1B C6B 106.99(9) . . ?
C9B C1B C6B 110.88(10) . . ?
O1B C1B C2B 110.07(10) . . ?
C9B C1B C2B 110.36(9) . . ?
C6B C1B C2B 110.14(10) . . ?
C3B C2B C1B 111.37(11) . . ?
C3B C2B H2B1 109.4 . . ?
C1B C2B H2B1 109.4 . . ?
C3B C2B H2B2 109.4 . . ?
C1B C2B H2B2 109.4 . . ?
H2B1 C2B H2B2 108.0 . . ?
C4B C3B C2B 110.81(12) . . ?
C4B C3B H3B1 109.5 . . ?
C2B C3B H3B1 109.5 . . ?
C4B C3B H3B2 109.5 . . ?
C2B C3B H3B2 109.5 . . ?
H3B1 C3B H3B2 108.1 . . ?
C5B C4B C3B 111.11(12) . . ?
C5B C4B H4B1 109.4 . . ?
C3B C4B H4B1 109.4 . . ?
C5B C4B H4B2 109.4 . . ?
C3B C4B H4B2 109.4 . . ?
H4B1 C4B H4B2 108.0 . . ?
C4B C5B C6B 111.56(12) . . ?
C4B C5B H5B1 109.3 . . ?
C6B C5B H5B1 109.3 . . ?
C4B C5B H5B2 109.3 . . ?
C6B C5B H5B2 109.3 . . ?
H5B1 C5B H5B2 108.0 . . ?
C5B C6B C1B 112.02(11) . . ?
C5B C6B H6B1 109.2 . . ?
C1B C6B H6B1 109.2 . . ?
C5B C6B H6B2 109.2 . . ?
C1B C6B H6B2 109.2 . . ?
H6B1 C6B H6B2 107.9 . . ?
C1C O1C H1C 109.5 . . ?
O1C C1C C7C 109.93(10) . . ?
O1C C1C C6C 110.48(9) . . ?
C7C C1C C6C 110.37(10) . . ?
O1C C1C C2C 106.90(9) . . ?
C7C C1C C2C 109.13(10) . . ?
C6C C1C C2C 109.95(10) . . ?
C3C C2C C1C 111.66(11) . . ?
C3C C2C H2C1 109.3 . . ?
C1C C2C H2C1 109.3 . . ?
C3C C2C H2C2 109.3 . . ?
C1C C2C H2C2 109.3 . . ?
H2C1 C2C H2C2 107.9 . . ?
C4C C3C C2C 111.21(11) . . ?
C4C C3C H3C1 109.4 . . ?
C2C C3C H3C1 109.4 . . ?
C4C C3C H3C2 109.4 . . ?
C2C C3C H3C2 109.4 . . ?
H3C1 C3C H3C2 108.0 . . ?
C5C C4C C3C 111.54(11) . . ?
C5C C4C H4C1 109.3 . . ?
C3C C4C H4C1 109.3 . . ?
C5C C4C H4C2 109.3 . . ?
C3C C4C H4C2 109.3 . . ?
H4C1 C4C H4C2 108.0 . . ?
C4C C5C C6C 111.06(13) . . ?
C4C C5C H5C1 109.4 . . ?
C6C C5C H5C1 109.4 . . ?
C4C C5C H5C2 109.4 . . ?
C6C C5C H5C2 109.4 . . ?
H5C1 C5C H5C2 108.0 . . ?
C5C C6C C1C 111.56(10) . . ?
C5C C6C H6C1 109.3 . . ?
C1C C6C H6C1 109.3 . . ?
C5C C6C H6C2 109.3 . . ?
C1C C6C H6C2 109.3 . . ?
H6C1 C6C H6C2 108.0 . . ?
C8C C7C C1C 174.92(13) . . ?
C7C C8C C8C 179.74(19) . 3_767 ?

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
O1A C1A C2A C3A -175.29(9) . . . . ?
C7A C1A C2A C3A 67.30(12) . . . . ?
C6A C1A C2A C3A -55.47(13) . . . . ?
C1A C2A C3A C4A 56.24(14) . . . . ?
C2A C3A C4A C5A -56.24(15) . . . . ?
C3A C4A C5A C6A 56.36(14) . . . . ?
C4A C5A C6A C1A -56.37(14) . . . . ?
O1A C1A C6A C5A 173.05(9) . . . . ?
C7A C1A C6A C5A -66.81(13) . . . . ?
C2A C1A C6A C5A 55.49(13) . . . . ?
O1B C1B C2B C3B 173.66(10) . . . . ?
C9B C1B C2B C3B -66.82(13) . . . . ?
C6B C1B C2B C3B 55.93(13) . . . . ?
C1B C2B C3B C4B -57.06(14) . . . . ?
C2B C3B C4B C5B 56.12(16) . . . . ?
C3B C4B C5B C6B -54.95(16) . . . . ?
C4B C5B C6B C1B 54.70(15) . . . . ?
O1B C1B C6B C5B -174.32(10) . . . . ?
C9B C1B C6B C5B 67.75(14) . . . . ?
C2B C1B C6B C5B -54.70(14) . . . . ?
O1C C1C C2C C3C -175.49(10) . . . . ?
C7C C1C C2C C3C 65.66(14) . . . . ?
C6C C1C C2C C3C -55.53(14) . . . . ?
C1C C2C C3C C4C 55.30(15) . . . . ?
C2C C3C C4C C5C -54.89(16) . . . . ?
C3C C4C C5C C6C 55.40(15) . . . . ?
C4C C5C C6C C1C -56.37(15) . . . . ?
O1C C1C C6C C5C 173.84(10) . . . . ?
C7C C1C C6C C5C -64.37(14) . . . . ?
C2C C1C C6C C5C 56.08(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1A H1A O1C 0.84 1.90 2.7369(16) 175.7 2_656
O1B H1B O1A 0.84 1.87 2.7041(12) 176.4 4_575
O1C H1C O1B 0.84 1.92 2.7316(13) 160.8 .

_refine_diff_density_max         0.394
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.067

_shelxl_version_number           2013-2

