# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_clor003

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 N2 O4, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C20 H24 N2 O5'
_chemical_formula_weight         372.41

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   7.4692(8)
_cell_length_b                   22.575(2)
_cell_length_c                   22.4145(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.242(6)
_cell_angle_gamma                90.00
_cell_volume                     3778.6(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2698
_cell_measurement_theta_min      2.9897
_cell_measurement_theta_max      25.2968

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1584
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_min  0.94819
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '120 images, ΔΦ 1.5°'

_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9812
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         23.53
_reflns_number_total             2692
_reflns_number_gt                2057
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;



_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0651P)²+10.6251P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2692
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0691
_refine_ls_wR_factor_ref         0.1808
_refine_ls_wR_factor_gt          0.1648
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.9246(3) 0.39254(11) 0.12540(11) 0.0473(7) Uani 1 1 d . . .
C3 C 0.9502(4) 0.35238(17) 0.08848(15) 0.0396(9) Uani 1 1 d . . .
C4 C 0.9046(4) 0.29124(15) 0.10216(13) 0.0339(8) Uani 1 1 d . . .
C5 C 0.8358(4) 0.27718(15) 0.15713(13) 0.0336(8) Uani 1 1 d . . .
H5 H 0.8054 0.2370 0.1646 0.040 Uiso 1 1 calc R . .
N6 N 0.8095(3) 0.31664(12) 0.20035(11) 0.0341(7) Uani 1 1 d . . .
H6 H 0.8387 0.3535 0.1925 0.041 Uiso 1 1 calc R . .
C7 C 0.7399(4) 0.30567(16) 0.25749(13) 0.0369(8) Uani 1 1 d . . .
C8 C 0.7137(5) 0.24925(18) 0.27974(15) 0.0492(10) Uani 1 1 d . . .
H8 H 0.7402 0.2156 0.2561 0.059 Uiso 1 1 calc R . .
C9 C 0.6484(6) 0.2421(2) 0.33673(16) 0.0606(12) Uani 1 1 d . . .
H9 H 0.6270 0.2033 0.3513 0.073 Uiso 1 1 calc R . .
C10 C 0.6142(5) 0.2899(2) 0.37245(16) 0.0635(13) Uani 1 1 d . . .
H10 H 0.5744 0.2842 0.4120 0.076 Uiso 1 1 calc R . .
C11 C 0.6380(5) 0.3461(2) 0.35042(16) 0.0558(12) Uani 1 1 d . . .
H11 H 0.6103 0.3794 0.3744 0.067 Uiso 1 1 calc R . .
C12 C 0.7023(4) 0.35465(17) 0.29332(14) 0.0413(9) Uani 1 1 d . . .
N13 N 0.7239(4) 0.41211(14) 0.26958(12) 0.0469(8) Uani 1 1 d . . .
H13 H 0.7051 0.4167 0.2310 0.056 Uiso 1 1 calc R . .
C14 C 0.7704(5) 0.45960(17) 0.30113(15) 0.0487(10) Uani 1 1 d . . .
H14 H 0.8067 0.4537 0.3416 0.058 Uiso 1 1 calc R . .
C15 C 0.7702(6) 0.51722(18) 0.27963(16) 0.0602(12) Uani 1 1 d . . .
C16 C 0.7075(7) 0.5282(2) 0.21862(18) 0.0769(16) Uani 1 1 d . . .
O17 O 0.6637(5) 0.48649(14) 0.18542(12) 0.0839(12) Uani 1 1 d . . .
C18 C 1.0322(6) 0.3695(2) 0.03067(17) 0.0658(12) Uani 1 1 d . . .
H18A H 1.0660 0.4114 0.0320 0.099 Uiso 1 1 calc R . .
H18B H 0.9454 0.3630 -0.0021 0.099 Uiso 1 1 calc R . .
H18C H 1.1390 0.3453 0.0242 0.099 Uiso 1 1 calc R . .
C19 C 0.9278(5) 0.24362(17) 0.05874(14) 0.0471(10) Uani 1 1 d . . .
O20 O 0.9738(5) 0.25290(15) 0.00795(12) 0.0863(11) Uani 1 1 d . . .
C21 C 0.8945(8) 0.18092(19) 0.07704(18) 0.0790(15) Uani 1 1 d . . .
H21A H 0.7687 0.1763 0.0878 0.118 Uiso 1 1 calc R . .
H21B H 0.9717 0.1710 0.1115 0.118 Uiso 1 1 calc R . .
H21C H 0.9211 0.1543 0.0438 0.118 Uiso 1 1 calc R . .
C22 C 0.8264(7) 0.5646(2) 0.32065(17) 0.0690(14) Uani 1 1 d . . .
O23 O 0.8098(6) 0.61768(14) 0.30845(12) 0.0933(13) Uani 1 1 d . . .
C24 C 0.9080(7) 0.54797(19) 0.38105(16) 0.0678(13) Uani 1 1 d . . .
H24A H 0.9559 0.5835 0.4007 0.102 Uiso 1 1 calc R . .
H24B H 1.0049 0.5194 0.3755 0.102 Uiso 1 1 calc R . .
H24C H 0.8157 0.5303 0.4059 0.102 Uiso 1 1 calc R . .
C25 C 0.7018(10) 0.5905(2) 0.19295(19) 0.115(3) Uani 1 1 d . . .
H25A H 0.6819 0.5884 0.1496 0.172 Uiso 1 1 calc R . .
H25B H 0.8157 0.6105 0.2017 0.172 Uiso 1 1 calc R . .
H25C H 0.6039 0.6127 0.2109 0.172 Uiso 1 1 calc R . .
C61 C 0.3379(7) 0.4820(2) -0.0223(2) 0.0806(16) Uani 1 1 d . . .
H61A H 0.2060 0.4864 -0.0242 0.097 Uiso 1 1 calc R . .
H61B H 0.3709 0.4494 -0.0494 0.097 Uiso 1 1 calc R . .
O62 O 0.3921(4) 0.46719(19) 0.03684(14) 0.1031(15) Uani 1 1 d . . .
C63 C 0.5792(5) 0.46308(17) 0.04220(15) 0.0487(10) Uani 1 1 d . . .
H63A H 0.6219 0.4296 0.0178 0.058 Uiso 1 1 calc R . .
H63B H 0.6142 0.4554 0.0843 0.058 Uiso 1 1 calc R . .


_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
O2 C3 1.245(4) . ?
C3 C4 1.456(5) . ?
C3 C18 1.496(5) . ?
C4 C5 1.382(4) . ?
C4 C19 1.463(5) . ?
C5 N6 1.334(4) . ?
C5 H5 0.9500 . ?
N6 C7 1.415(4) . ?
N6 H6 0.8800 . ?
C7 C8 1.383(5) . ?
C7 C12 1.399(5) . ?
C8 C9 1.387(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.371(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.374(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(5) . ?
C11 H11 0.9500 . ?
C12 N13 1.413(5) . ?
N13 C14 1.327(5) . ?
N13 H13 0.8800 . ?
C14 C15 1.387(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.457(5) . ?
C15 C22 1.466(6) . ?
C16 O17 1.240(5) . ?
C16 C25 1.520(7) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 O20 1.214(4) . ?
C19 C21 1.496(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 O23 1.235(5) . ?
C22 C24 1.519(5) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C61 O62 1.417(5) . ?
C61 C63 1.460(6) 5_665 ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
O62 C63 1.402(5) . ?
C63 C61 1.460(6) 5_665 ?
C63 H63A 0.9900 . ?
C63 H63B 0.9900 . ?

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 C3 C4 120.7(3) . . ?
O2 C3 C18 117.3(3) . . ?
C4 C3 C18 122.0(3) . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 C19 118.4(3) . . ?
C3 C4 C19 121.7(3) . . ?
N6 C5 C4 123.9(3) . . ?
N6 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C5 N6 C7 127.1(3) . . ?
C5 N6 H6 116.4 . . ?
C7 N6 H6 116.4 . . ?
C8 C7 C12 119.3(3) . . ?
C8 C7 N6 123.0(3) . . ?
C12 C7 N6 117.6(3) . . ?
C7 C8 C9 119.6(4) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 121.4(4) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 119.3(3) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C10 C11 C12 120.6(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 119.8(4) . . ?
C11 C12 N13 121.3(3) . . ?
C7 C12 N13 118.9(3) . . ?
C14 N13 C12 124.9(3) . . ?
C14 N13 H13 117.6 . . ?
C12 N13 H13 117.6 . . ?
N13 C14 C15 125.1(3) . . ?
N13 C14 H14 117.5 . . ?
C15 C14 H14 117.5 . . ?
C14 C15 C16 118.9(4) . . ?
C14 C15 C22 117.9(3) . . ?
C16 C15 C22 123.1(4) . . ?
O17 C16 C15 120.6(4) . . ?
O17 C16 C25 118.1(4) . . ?
C15 C16 C25 121.3(4) . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O20 C19 C4 122.5(4) . . ?
O20 C19 C21 118.2(4) . . ?
C4 C19 C21 119.4(3) . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O23 C22 C15 122.9(3) . . ?
O23 C22 C24 118.3(4) . . ?
C15 C22 C24 118.8(4) . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C16 C25 H25A 109.5 . . ?
C16 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C16 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O62 C61 C63 111.9(4) . 5_665 ?
O62 C61 H61A 109.2 . . ?
C63 C61 H61A 109.2 5_665 . ?
O62 C61 H61B 109.2 . . ?
C63 C61 H61B 109.2 5_665 . ?
H61A C61 H61B 107.9 . . ?
C63 O62 C61 111.1(3) . . ?
O62 C63 C61 110.3(4) . 5_665 ?
O62 C63 H63A 109.6 . . ?
C61 C63 H63A 109.6 5_665 . ?
O62 C63 H63B 109.6 . . ?
C61 C63 H63B 109.6 5_665 . ?
H63A C63 H63B 108.1 . . ?

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
O2 C3 C4 C5 -1.4(5) . . . . ?
C18 C3 C4 C5 177.4(3) . . . . ?
O2 C3 C4 C19 177.9(3) . . . . ?
C18 C3 C4 C19 -3.4(5) . . . . ?
C3 C4 C5 N6 -1.1(5) . . . . ?
C19 C4 C5 N6 179.7(3) . . . . ?
C4 C5 N6 C7 180.0(3) . . . . ?
C5 N6 C7 C8 10.1(5) . . . . ?
C5 N6 C7 C12 -172.1(3) . . . . ?
C12 C7 C8 C9 0.9(5) . . . . ?
N6 C7 C8 C9 178.6(3) . . . . ?
C7 C8 C9 C10 -2.0(6) . . . . ?
C8 C9 C10 C11 2.7(6) . . . . ?
C9 C10 C11 C12 -2.3(6) . . . . ?
C10 C11 C12 C7 1.3(5) . . . . ?
C10 C11 C12 N13 178.6(3) . . . . ?
C8 C7 C12 C11 -0.5(5) . . . . ?
N6 C7 C12 C11 -178.4(3) . . . . ?
C8 C7 C12 N13 -178.0(3) . . . . ?
N6 C7 C12 N13 4.2(4) . . . . ?
C11 C12 N13 C14 33.7(5) . . . . ?
C7 C12 N13 C14 -149.0(3) . . . . ?
C12 N13 C14 C15 -171.5(4) . . . . ?
N13 C14 C15 C16 2.8(7) . . . . ?
N13 C14 C15 C22 -179.8(4) . . . . ?
C14 C15 C16 O17 -3.6(7) . . . . ?
C22 C15 C16 O17 179.0(5) . . . . ?
C14 C15 C16 C25 179.1(5) . . . . ?
C22 C15 C16 C25 1.8(8) . . . . ?
C5 C4 C19 O20 174.0(4) . . . . ?
C3 C4 C19 O20 -5.3(6) . . . . ?
C5 C4 C19 C21 -6.2(5) . . . . ?
C3 C4 C19 C21 174.5(4) . . . . ?
C14 C15 C22 O23 -170.6(5) . . . . ?
C16 C15 C22 O23 6.7(8) . . . . ?
C14 C15 C22 C24 9.0(7) . . . . ?
C16 C15 C22 C24 -173.6(5) . . . . ?
C63 C61 O62 C63 -56.3(6) 5_665 . . . ?
C61 O62 C63 C61 55.4(6) . . . 5_665 ?

_diffrn_measured_fraction_theta_max 0.954
_diffrn_reflns_theta_full        23.53
_diffrn_measured_fraction_theta_full 0.954
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.052


_database_code_depnum_ccdc_archive 'CCDC 995462'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cl105

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C18 H18 Cu N2 O4, C H Cl3'
_chemical_formula_sum            'C19 H19 Cl3 Cu N2 O4'
_chemical_formula_weight         509.25

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'A b a 2'
_symmetry_space_group_name_Hall  'A 2 -2ac'

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

_cell_length_a                   27.317(3)
_cell_length_b                   22.2583(14)
_cell_length_c                   6.9575(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4230.3(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3809
_cell_measurement_theta_min      2.3559
_cell_measurement_theta_max      25.3293

_exptl_crystal_description       plate
_exptl_crystal_colour            brown-red
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2072
_exptl_absorpt_coefficient_mu    1.440
_exptl_absorpt_correction_T_min  0.93930
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '100 images, ΔΦ 2.0° '
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15226
_diffrn_reflns_av_R_equivalents  0.0873
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         25.38
_reflns_number_total             3875
_reflns_number_gt                3207
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0447P)²+26.1396P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_number_reflns         3875
_refine_ls_number_parameters     266
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1310
_refine_ls_wR_factor_gt          0.1213
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.293936(18) 0.06377(2) 0.16739(11) 0.01885(12) Uani 1 1 d . . .
O2 O 0.30269(11) 0.14444(14) 0.2524(5) 0.0230(8) Uani 1 1 d . . .
C3 C 0.27080(18) 0.1842(2) 0.2908(7) 0.0203(11) Uani 1 1 d . . .
C4 C 0.21960(17) 0.1730(2) 0.2876(7) 0.0179(11) Uani 1 1 d . . .
C5 C 0.19987(17) 0.1170(2) 0.2379(7) 0.0173(10) Uani 1 1 d . . .
H5 H 0.1653 0.1133 0.2442 0.021 Uiso 1 1 calc R . .
N6 N 0.22439(12) 0.06878(15) 0.1832(7) 0.0180(8) Uani 1 1 d . . .
C7 C 0.20120(15) 0.01347(18) 0.1343(7) 0.0167(11) Uani 1 1 d . . .
C8 C 0.15129(17) 0.0043(2) 0.1160(7) 0.0238(12) Uani 1 1 d . . .
H8 H 0.1294 0.0371 0.1323 0.029 Uiso 1 1 calc R . .
C9 C 0.13303(17) -0.0520(2) 0.0743(7) 0.0227(12) Uani 1 1 d . . .
H9 H 0.0987 -0.0579 0.0637 0.027 Uiso 1 1 calc R . .
C10 C 0.16468(18) -0.0999(2) 0.0477(7) 0.0216(12) Uani 1 1 d . . .
H10 H 0.1519 -0.1387 0.0211 0.026 Uiso 1 1 calc R . .
C11 C 0.21419(18) -0.0917(2) 0.0594(7) 0.0216(12) Uani 1 1 d . . .
H11 H 0.2356 -0.1247 0.0389 0.026 Uiso 1 1 calc R . .
C12 C 0.23371(16) -0.0349(2) 0.1016(6) 0.0179(11) Uani 1 1 d . . .
N13 N 0.28430(13) -0.01937(16) 0.1110(5) 0.0170(10) Uani 1 1 d . . .
C14 C 0.31961(17) -0.0590(2) 0.0908(7) 0.0213(11) Uani 1 1 d . . .
H14 H 0.3102 -0.0998 0.0751 0.026 Uiso 1 1 calc R . .
C15 C 0.36996(17) -0.0463(2) 0.0904(7) 0.0199(11) Uani 1 1 d . . .
C16 C 0.38815(18) 0.0132(2) 0.0862(8) 0.0273(12) Uani 1 1 d . . .
O17 O 0.36169(11) 0.05967(13) 0.1090(5) 0.0255(9) Uani 1 1 d . . .
C18 C 0.29332(18) 0.2446(2) 0.3411(7) 0.0253(12) Uani 1 1 d . . .
H18A H 0.3288 0.2401 0.3558 0.038 Uiso 1 1 calc R . .
H18B H 0.2792 0.2593 0.4618 0.038 Uiso 1 1 calc R . .
H18C H 0.2865 0.2734 0.2381 0.038 Uiso 1 1 calc R . .
C19 C 0.18422(19) 0.2207(2) 0.3371(7) 0.0230(12) Uani 1 1 d . . .
O20 O 0.19556(13) 0.27409(16) 0.3442(6) 0.0354(10) Uani 1 1 d . . .
C21 C 0.13160(18) 0.2045(2) 0.3784(8) 0.0309(14) Uani 1 1 d . . .
H21A H 0.1155 0.2380 0.4444 0.046 Uiso 1 1 calc R . .
H21B H 0.1306 0.1687 0.4603 0.046 Uiso 1 1 calc R . .
H21C H 0.1146 0.1962 0.2573 0.046 Uiso 1 1 calc R . .
C22 C 0.40388(18) -0.0983(2) 0.0857(8) 0.0270(12) Uani 1 1 d . . .
O23 O 0.44700(12) -0.09232(16) 0.1360(7) 0.0428(11) Uani 1 1 d . . .
C24 C 0.3859(2) -0.1588(2) 0.0274(8) 0.0324(14) Uani 1 1 d . . .
H24A H 0.4138 -0.1861 0.0136 0.049 Uiso 1 1 calc R . .
H24B H 0.3686 -0.1557 -0.0956 0.049 Uiso 1 1 calc R . .
H24C H 0.3636 -0.1743 0.1258 0.049 Uiso 1 1 calc R . .
C25 C 0.44070(19) 0.0271(3) 0.0489(10) 0.0391(16) Uani 1 1 d . . .
H25A H 0.4438 0.0689 0.0064 0.059 Uiso 1 1 calc R . .
H25B H 0.4532 0.0003 -0.0513 0.059 Uiso 1 1 calc R . .
H25C H 0.4596 0.0213 0.1672 0.059 Uiso 1 1 calc R . .
C31 C 0.4861(3) 0.1475(4) 0.4433(10) 0.058(2) Uani 1 1 d . . .
H31 H 0.5052 0.1361 0.3262 0.069 Uiso 1 1 calc R . .
Cl32 Cl 0.42544(7) 0.16021(11) 0.3763(3) 0.0703(6) Uani 1 1 d . . .
Cl33 Cl 0.48625(11) 0.08748(18) 0.6002(5) 0.1863(15) Uani 1 1 d . . .
Cl34 Cl 0.51135(12) 0.2108(2) 0.5403(6) 0.1808(17) 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
Cu1 O17 1.897(3) . ?
Cu1 O2 1.905(3) . ?
Cu1 N6 1.906(3) . ?
Cu1 N13 1.910(4) . ?
O2 C3 1.270(6) . ?
C3 C4 1.421(7) . ?
C3 C18 1.519(7) . ?
C4 C5 1.403(6) . ?
C4 C19 1.476(7) . ?
C5 N6 1.320(6) . ?
C5 H5 0.9500 . ?
N6 C7 1.426(5) . ?
C7 C8 1.384(6) . ?
C7 C12 1.413(6) . ?
C8 C9 1.379(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.367(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.403(6) . ?
C11 H11 0.9500 . ?
C12 N13 1.426(5) . ?
N13 C14 1.315(6) . ?
C14 C15 1.404(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.415(7) . ?
C15 C22 1.482(7) . ?
C16 O17 1.272(6) . ?
C16 C25 1.491(7) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 O20 1.228(6) . ?
C19 C21 1.510(7) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 O23 1.236(6) . ?
C22 C24 1.488(7) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C31 Cl34 1.709(8) . ?
C31 Cl33 1.724(8) . ?
C31 Cl32 1.745(7) . ?
C31 H31 1.0000 . ?

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
O17 Cu1 O2 89.39(13) . . ?
O17 Cu1 N6 170.93(18) . . ?
O2 Cu1 N6 92.99(14) . . ?
O17 Cu1 N13 92.52(14) . . ?
O2 Cu1 N13 173.74(16) . . ?
N6 Cu1 N13 86.05(15) . . ?
C3 O2 Cu1 129.5(3) . . ?
O2 C3 C4 123.4(4) . . ?
O2 C3 C18 112.8(4) . . ?
C4 C3 C18 123.8(4) . . ?
C5 C4 C3 122.5(4) . . ?
C5 C4 C19 116.5(4) . . ?
C3 C4 C19 121.0(4) . . ?
N6 C5 C4 126.8(4) . . ?
N6 C5 H5 116.6 . . ?
C4 C5 H5 116.6 . . ?
C5 N6 C7 123.0(4) . . ?
C5 N6 Cu1 124.7(3) . . ?
C7 N6 Cu1 112.2(3) . . ?
C8 C7 C12 119.5(4) . . ?
C8 C7 N6 125.9(4) . . ?
C12 C7 N6 114.6(4) . . ?
C9 C8 C7 120.6(4) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.1(4) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.4(4) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.6(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 118.7(4) . . ?
C11 C12 N13 126.6(4) . . ?
C7 C12 N13 114.7(4) . . ?
C14 N13 C12 122.9(4) . . ?
C14 N13 Cu1 124.8(3) . . ?
C12 N13 Cu1 112.2(3) . . ?
N13 C14 C15 125.7(4) . . ?
N13 C14 H14 117.1 . . ?
C15 C14 H14 117.1 . . ?
C14 C15 C16 122.1(4) . . ?
C14 C15 C22 117.1(4) . . ?
C16 C15 C22 120.7(4) . . ?
O17 C16 C15 124.0(5) . . ?
O17 C16 C25 113.5(4) . . ?
C15 C16 C25 122.4(4) . . ?
C16 O17 Cu1 128.3(3) . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O20 C19 C4 122.7(5) . . ?
O20 C19 C21 117.7(4) . . ?
C4 C19 C21 119.7(4) . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O23 C22 C15 120.4(5) . . ?
O23 C22 C24 119.2(5) . . ?
C15 C22 C24 120.4(4) . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C16 C25 H25A 109.5 . . ?
C16 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C16 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
Cl34 C31 Cl33 112.9(5) . . ?
Cl34 C31 Cl32 110.7(4) . . ?
Cl33 C31 Cl32 107.3(4) . . ?
Cl34 C31 H31 108.6 . . ?
Cl33 C31 H31 108.6 . . ?
Cl32 C31 H31 108.6 . . ?

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
O17 Cu1 O2 C3 167.8(4) . . . . ?
N6 Cu1 O2 C3 -3.4(4) . . . . ?
Cu1 O2 C3 C4 4.3(7) . . . . ?
Cu1 O2 C3 C18 -176.0(3) . . . . ?
O2 C3 C4 C5 -1.2(7) . . . . ?
C18 C3 C4 C5 179.1(4) . . . . ?
O2 C3 C4 C19 178.8(4) . . . . ?
C18 C3 C4 C19 -0.9(7) . . . . ?
C3 C4 C5 N6 -2.2(8) . . . . ?
C19 C4 C5 N6 177.8(5) . . . . ?
C4 C5 N6 C7 -179.7(4) . . . . ?
C4 C5 N6 Cu1 2.2(7) . . . . ?
O2 Cu1 N6 C5 0.2(4) . . . . ?
N13 Cu1 N6 C5 174.0(4) . . . . ?
O2 Cu1 N6 C7 -178.1(3) . . . . ?
N13 Cu1 N6 C7 -4.3(3) . . . . ?
C5 N6 C7 C8 7.7(8) . . . . ?
Cu1 N6 C7 C8 -174.0(4) . . . . ?
C5 N6 C7 C12 -172.8(4) . . . . ?
Cu1 N6 C7 C12 5.5(5) . . . . ?
C12 C7 C8 C9 2.8(7) . . . . ?
N6 C7 C8 C9 -177.7(5) . . . . ?
C7 C8 C9 C10 -0.9(7) . . . . ?
C8 C9 C10 C11 -1.1(8) . . . . ?
C9 C10 C11 C12 1.0(7) . . . . ?
C10 C11 C12 C7 0.9(7) . . . . ?
C10 C11 C12 N13 -177.4(4) . . . . ?
C8 C7 C12 C11 -2.7(7) . . . . ?
N6 C7 C12 C11 177.7(4) . . . . ?
C8 C7 C12 N13 175.8(4) . . . . ?
N6 C7 C12 N13 -3.8(6) . . . . ?
C11 C12 N13 C14 -4.0(7) . . . . ?
C7 C12 N13 C14 177.6(4) . . . . ?
C11 C12 N13 Cu1 178.6(4) . . . . ?
C7 C12 N13 Cu1 0.3(5) . . . . ?
O17 Cu1 N13 C14 13.9(4) . . . . ?
N6 Cu1 N13 C14 -175.0(4) . . . . ?
O17 Cu1 N13 C12 -168.8(3) . . . . ?
N6 Cu1 N13 C12 2.2(3) . . . . ?
C12 N13 C14 C15 177.1(4) . . . . ?
Cu1 N13 C14 C15 -5.9(7) . . . . ?
N13 C14 C15 C16 -8.8(8) . . . . ?
N13 C14 C15 C22 173.9(5) . . . . ?
C14 C15 C16 O17 10.1(8) . . . . ?
C22 C15 C16 O17 -172.7(5) . . . . ?
C14 C15 C16 C25 -168.3(5) . . . . ?
C22 C15 C16 C25 8.9(8) . . . . ?
C15 C16 O17 Cu1 3.8(8) . . . . ?
C25 C16 O17 Cu1 -177.7(4) . . . . ?
O2 Cu1 O17 C16 160.7(4) . . . . ?
N13 Cu1 O17 C16 -13.3(4) . . . . ?
C5 C4 C19 O20 -164.6(5) . . . . ?
C3 C4 C19 O20 15.4(8) . . . . ?
C5 C4 C19 C21 14.5(7) . . . . ?
C3 C4 C19 C21 -165.5(4) . . . . ?
C14 C15 C22 O23 -160.5(5) . . . . ?
C16 C15 C22 O23 22.1(8) . . . . ?
C14 C15 C22 C24 17.1(7) . . . . ?
C16 C15 C22 C24 -160.2(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.954
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.093

_database_code_depnum_ccdc_archive 'CCDC 995463'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cl106

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 Cu N2 O4, 2(H2 O)'
_chemical_formula_sum            'C18 H22 Cu N2 O6'
_chemical_formula_weight         425.92

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P bca'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   8.0257(3)
_cell_length_b                   19.2831(6)
_cell_length_c                   23.3907(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3620.0(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    13020
_cell_measurement_theta_min      2.6071
_cell_measurement_theta_max      25.7244

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1768
_exptl_absorpt_coefficient_mu    1.245
_exptl_absorpt_correction_T_min  0.87817
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
two datasets measured, integrated and corrected for absorption 
individually (crysalis); merged with prep
rint set 1 0.033 (94.6% compl)
rint set 2 0.027 (55.4% compl)
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
200 images, ΔΦ 1.2° 
34 images, ΔΦ 1.2° (2nd orientation)
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3421
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0105
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         25.78
_reflns_number_total             3421
_reflns_number_gt                3129
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0485P)²+6.5600P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3421
_refine_ls_number_parameters     254
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0989
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.028
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.11848(4) 0.142946(15) 0.307174(12) 0.02120(12) Uani 1 1 d . . .
O2 O -0.0129(2) 0.22490(9) 0.31490(7) 0.0258(4) Uani 1 1 d . . .
C3 C -0.0735(3) 0.26468(12) 0.27700(11) 0.0231(5) Uani 1 1 d . . .
C4 C -0.0578(3) 0.25196(12) 0.21689(11) 0.0233(5) Uani 1 1 d . . .
C5 C 0.0322(3) 0.19414(12) 0.19540(10) 0.0225(5) Uani 1 1 d . . .
H5 H 0.0361 0.1892 0.1550 0.027 Uiso 1 1 calc R . .
N6 N 0.1105(2) 0.14690(10) 0.22543(9) 0.0201(4) Uani 1 1 d . . .
C7 C 0.2012(3) 0.09234(12) 0.19959(10) 0.0213(5) Uani 1 1 d . . .
C8 C 0.2230(3) 0.08298(13) 0.14080(10) 0.0261(5) Uani 1 1 d . . .
H8 H 0.1735 0.1145 0.1146 0.031 Uiso 1 1 calc R . .
C9 C 0.3168(3) 0.02770(13) 0.12075(10) 0.0261(5) Uani 1 1 d . . .
H9 H 0.3317 0.0215 0.0808 0.031 Uiso 1 1 calc R . .
C10 C 0.3895(3) -0.01878(13) 0.15897(11) 0.0264(5) Uani 1 1 d . . .
H10 H 0.4528 -0.0568 0.1450 0.032 Uiso 1 1 calc R . .
C11 C 0.3699(3) -0.00974(13) 0.21716(11) 0.0247(5) Uani 1 1 d . . .
H11 H 0.4202 -0.0414 0.2431 0.030 Uiso 1 1 calc R . .
C12 C 0.2759(3) 0.04595(12) 0.23803(10) 0.0205(5) Uani 1 1 d . . .
N13 N 0.2491(3) 0.06112(10) 0.29650(8) 0.0208(4) Uani 1 1 d . . .
C14 C 0.2993(3) 0.02010(12) 0.33748(10) 0.0224(5) Uani 1 1 d . . .
H14 H 0.3605 -0.0198 0.3262 0.027 Uiso 1 1 calc R . .
C15 C 0.2723(3) 0.02885(13) 0.39697(10) 0.0233(5) Uani 1 1 d . . .
C16 C 0.1902(3) 0.08813(12) 0.41990(10) 0.0242(5) Uani 1 1 d . . .
O17 O 0.1356(2) 0.13758(9) 0.38873(8) 0.0261(4) Uani 1 1 d . . .
C18 C -0.1618(3) 0.32670(13) 0.30101(11) 0.0277(5) Uani 1 1 d . . .
H18A H -0.1715 0.3219 0.3426 0.042 Uiso 1 1 calc R . .
H18B H -0.2733 0.3301 0.2841 0.042 Uiso 1 1 calc R . .
H18C H -0.0983 0.3687 0.2920 0.042 Uiso 1 1 calc R . .
C19 C -0.1231(3) 0.30198(13) 0.17461(12) 0.0272(5) Uani 1 1 d . . .
O20 O -0.1951(3) 0.35528(10) 0.18831(8) 0.0411(5) Uani 1 1 d . . .
C21 C -0.0977(4) 0.28841(15) 0.11143(11) 0.0355(6) Uani 1 1 d . . .
H21A H -0.1473 0.3263 0.0892 0.053 Uiso 1 1 calc R . .
H21B H -0.1512 0.2445 0.1010 0.053 Uiso 1 1 calc R . .
H21C H 0.0218 0.2857 0.1032 0.053 Uiso 1 1 calc R . .
C22 C 0.3299(3) -0.02894(13) 0.43342(11) 0.0253(5) Uani 1 1 d . . .
O23 O 0.2726(3) -0.04086(10) 0.48107(8) 0.0391(5) Uani 1 1 d . . .
C24 C 0.4604(3) -0.07764(13) 0.40994(11) 0.0273(5) Uani 1 1 d . . .
H24A H 0.5123 -0.1032 0.4415 0.041 Uiso 1 1 calc R . .
H24B H 0.5456 -0.0509 0.3896 0.041 Uiso 1 1 calc R . .
H24C H 0.4079 -0.1105 0.3835 0.041 Uiso 1 1 calc R . .
C25 C 0.1619(4) 0.09815(14) 0.48268(11) 0.0338(6) Uani 1 1 d . . .
H25A H 0.1527 0.1478 0.4911 0.051 Uiso 1 1 calc R . .
H25B H 0.2558 0.0785 0.5040 0.051 Uiso 1 1 calc R . .
H25C H 0.0588 0.0747 0.4940 0.051 Uiso 1 1 calc R . .
O31 O 0.9312(3) 0.25608(11) 0.44893(9) 0.0413(5) Uani 1 1 d GD . .
H31A H 0.9746 0.2347 0.4225 0.050 Uiso 1 1 d GD . .
H31B H 0.8481 0.2334 0.4570 0.050 Uiso 1 1 d GD . .
O32 O 0.1468(3) 0.32112(11) 0.52577(8) 0.0374(5) Uani 1 1 d GD . .
H32A H 0.1705 0.3589 0.5119 0.045 Uiso 1 1 d GD . .
H32B H 0.0870 0.3027 0.5018 0.045 Uiso 1 1 d GD . .


_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
Cu1 O2 1.9081(18) . ?
Cu1 N13 1.911(2) . ?
Cu1 N6 1.915(2) . ?
Cu1 O17 1.9153(18) . ?
O2 C3 1.269(3) . ?
C3 C4 1.433(3) . ?
C3 C18 1.499(3) . ?
C4 C5 1.421(3) . ?
C4 C19 1.478(3) . ?
C5 N6 1.311(3) . ?
C5 H5 0.9500 . ?
N6 C7 1.415(3) . ?
C7 C8 1.398(3) . ?
C7 C12 1.403(3) . ?
C8 C9 1.387(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.400(3) . ?
C11 H11 0.9500 . ?
C12 N13 1.415(3) . ?
N13 C14 1.306(3) . ?
C14 C15 1.419(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.424(4) . ?
C15 C22 1.477(3) . ?
C16 O17 1.278(3) . ?
C16 C25 1.498(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 O20 1.222(3) . ?
C19 C21 1.515(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 O23 1.228(3) . ?
C22 C24 1.510(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
O31 H31A 0.8200 . ?
O31 H31B 0.8200 . ?
O32 H32A 0.8200 . ?
O32 H32B 0.8200 . ?

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 Cu1 N13 177.92(8) . . ?
O2 Cu1 N6 92.47(8) . . ?
N13 Cu1 N6 85.45(8) . . ?
O2 Cu1 O17 89.44(7) . . ?
N13 Cu1 O17 92.64(8) . . ?
N6 Cu1 O17 177.64(8) . . ?
C3 O2 Cu1 130.27(16) . . ?
O2 C3 C4 123.2(2) . . ?
O2 C3 C18 113.7(2) . . ?
C4 C3 C18 123.1(2) . . ?
C5 C4 C3 121.8(2) . . ?
C5 C4 C19 117.1(2) . . ?
C3 C4 C19 120.9(2) . . ?
N6 C5 C4 126.8(2) . . ?
N6 C5 H5 116.6 . . ?
C4 C5 H5 116.6 . . ?
C5 N6 C7 122.3(2) . . ?
C5 N6 Cu1 125.37(17) . . ?
C7 N6 Cu1 112.32(15) . . ?
C8 C7 C12 119.6(2) . . ?
C8 C7 N6 125.5(2) . . ?
C12 C7 N6 114.9(2) . . ?
C9 C8 C7 120.0(2) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.3(2) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.1(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 119.7(2) . . ?
C11 C12 N13 125.3(2) . . ?
C7 C12 N13 115.0(2) . . ?
C14 N13 C12 122.5(2) . . ?
C14 N13 Cu1 125.00(17) . . ?
C12 N13 Cu1 112.37(15) . . ?
N13 C14 C15 126.9(2) . . ?
N13 C14 H14 116.6 . . ?
C15 C14 H14 116.6 . . ?
C14 C15 C16 122.4(2) . . ?
C14 C15 C22 115.4(2) . . ?
C16 C15 C22 122.2(2) . . ?
O17 C16 C15 122.9(2) . . ?
O17 C16 C25 114.3(2) . . ?
C15 C16 C25 122.9(2) . . ?
C16 O17 Cu1 129.30(16) . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O20 C19 C4 122.8(2) . . ?
O20 C19 C21 117.7(2) . . ?
C4 C19 C21 119.5(2) . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O23 C22 C15 123.2(2) . . ?
O23 C22 C24 118.3(2) . . ?
C15 C22 C24 118.4(2) . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C16 C25 H25A 109.5 . . ?
C16 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C16 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
H31A O31 H31B 104.5 . . ?
H32A O32 H32B 104.5 . . ?

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
N6 Cu1 O2 C3 -1.5(2) . . . . ?
O17 Cu1 O2 C3 177.1(2) . . . . ?
Cu1 O2 C3 C4 2.9(4) . . . . ?
Cu1 O2 C3 C18 -176.52(17) . . . . ?
O2 C3 C4 C5 -1.8(4) . . . . ?
C18 C3 C4 C5 177.5(2) . . . . ?
O2 C3 C4 C19 -176.7(2) . . . . ?
C18 C3 C4 C19 2.6(4) . . . . ?
C3 C4 C5 N6 -0.5(4) . . . . ?
C19 C4 C5 N6 174.6(2) . . . . ?
C4 C5 N6 C7 -178.0(2) . . . . ?
C4 C5 N6 Cu1 1.6(4) . . . . ?
O2 Cu1 N6 C5 -0.7(2) . . . . ?
N13 Cu1 N6 C5 179.2(2) . . . . ?
O2 Cu1 N6 C7 178.94(16) . . . . ?
N13 Cu1 N6 C7 -1.16(16) . . . . ?
C5 N6 C7 C8 2.0(4) . . . . ?
Cu1 N6 C7 C8 -177.6(2) . . . . ?
C5 N6 C7 C12 -179.4(2) . . . . ?
Cu1 N6 C7 C12 1.0(3) . . . . ?
C12 C7 C8 C9 0.6(4) . . . . ?
N6 C7 C8 C9 179.1(2) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
C10 C11 C12 C7 0.3(4) . . . . ?
C10 C11 C12 N13 -179.0(2) . . . . ?
C8 C7 C12 C11 -0.8(3) . . . . ?
N6 C7 C12 C11 -179.5(2) . . . . ?
C8 C7 C12 N13 178.6(2) . . . . ?
N6 C7 C12 N13 -0.1(3) . . . . ?
C11 C12 N13 C14 -6.0(4) . . . . ?
C7 C12 N13 C14 174.6(2) . . . . ?
C11 C12 N13 Cu1 178.51(19) . . . . ?
C7 C12 N13 Cu1 -0.9(3) . . . . ?
N6 Cu1 N13 C14 -174.2(2) . . . . ?
O17 Cu1 N13 C14 7.2(2) . . . . ?
N6 Cu1 N13 C12 1.11(16) . . . . ?
O17 Cu1 N13 C12 -177.50(16) . . . . ?
C12 N13 C14 C15 -176.9(2) . . . . ?
Cu1 N13 C14 C15 -2.0(4) . . . . ?
N13 C14 C15 C16 -3.3(4) . . . . ?
N13 C14 C15 C22 174.6(2) . . . . ?
C14 C15 C16 O17 -0.2(4) . . . . ?
C22 C15 C16 O17 -178.0(2) . . . . ?
C14 C15 C16 C25 -179.6(2) . . . . ?
C22 C15 C16 C25 2.6(4) . . . . ?
C15 C16 O17 Cu1 9.0(4) . . . . ?
C25 C16 O17 Cu1 -171.56(18) . . . . ?
O2 Cu1 O17 C16 168.9(2) . . . . ?
N13 Cu1 O17 C16 -11.0(2) . . . . ?
C5 C4 C19 O20 -176.3(3) . . . . ?
C3 C4 C19 O20 -1.2(4) . . . . ?
C5 C4 C19 C21 2.3(4) . . . . ?
C3 C4 C19 C21 177.4(2) . . . . ?
C14 C15 C22 O23 -156.1(3) . . . . ?
C16 C15 C22 O23 21.9(4) . . . . ?
C14 C15 C22 C24 21.1(3) . . . . ?
C16 C15 C22 C24 -160.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.069

_database_code_depnum_ccdc_archive 'CCDC 995464'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cl112

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 Cu N2 O4'
_chemical_formula_sum            'C18 H18 Cu N2 O4'
_chemical_formula_weight         389.88

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'
Cu Cu 0.3201 1.2651 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   11.2596(2)
_cell_length_b                   23.9363(4)
_cell_length_c                   6.9871(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.591(2)
_cell_angle_gamma                90.00
_cell_volume                     1830.38(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7299
_cell_measurement_theta_min      3.1116
_cell_measurement_theta_max      25.9477

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             804
_exptl_absorpt_coefficient_mu    1.217
_exptl_absorpt_correction_T_min  0.75211
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '481 images, ΔΦ 0.5° '
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16627
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3403
_reflns_number_gt                3144
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;



_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0516P)²+3.4531P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3403
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1134
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.77904(3) 0.190140(14) 0.56425(5) 0.02338(14) Uani 1 1 d . . .
O2 O 0.78912(19) 0.11107(9) 0.6002(3) 0.0326(5) Uani 1 1 d . . .
C3 C 0.8812(3) 0.08074(13) 0.6784(5) 0.0335(7) Uani 1 1 d . . .
C4 C 0.9985(3) 0.10315(12) 0.7630(5) 0.0283(6) Uani 1 1 d . . .
C5 C 1.0202(3) 0.16136(11) 0.7814(4) 0.0225(6) Uani 1 1 d . . .
H5 H 1.1000 0.1726 0.8486 0.027 Uiso 1 1 calc R . .
N6 N 0.9425(2) 0.20120(9) 0.7161(3) 0.0203(5) Uani 1 1 d . . .
C7 C 0.9724(2) 0.25857(11) 0.7432(4) 0.0191(5) Uani 1 1 d . . .
C8 C 1.0848(2) 0.28014(11) 0.8449(4) 0.0221(6) Uani 1 1 d . . .
H8 H 1.1500 0.2555 0.8997 0.026 Uiso 1 1 calc R . .
C9 C 1.1014(3) 0.33727(12) 0.8664(4) 0.0256(6) Uani 1 1 d . . .
H9 H 1.1781 0.3517 0.9355 0.031 Uiso 1 1 calc R . .
C10 C 1.0061(3) 0.37360(12) 0.7870(5) 0.0286(6) Uani 1 1 d . . .
H10 H 1.0177 0.4128 0.8040 0.034 Uiso 1 1 calc R . .
C11 C 0.8951(3) 0.35314(12) 0.6841(5) 0.0280(6) Uani 1 1 d . . .
H11 H 0.8307 0.3783 0.6297 0.034 Uiso 1 1 calc R . .
C12 C 0.8768(2) 0.29591(11) 0.6594(4) 0.0201(5) Uani 1 1 d . . .
N13 N 0.7677(2) 0.26962(10) 0.5539(3) 0.0234(5) Uani 1 1 d . . .
C14 C 0.6723(3) 0.29862(13) 0.4629(4) 0.0271(6) Uani 1 1 d . . .
H14 H 0.6801 0.3381 0.4664 0.033 Uiso 1 1 calc R . .
C15 C 0.5577(3) 0.27632(15) 0.3591(4) 0.0338(7) Uani 1 1 d . . .
C16 C 0.5354(3) 0.21779(16) 0.3413(4) 0.0346(7) Uani 1 1 d . . .
O17 O 0.61678(19) 0.18122(10) 0.4065(3) 0.0341(5) Uani 1 1 d . . .
C18 C 0.8539(3) 0.01950(15) 0.6743(9) 0.0666(14) Uani 1 1 d . . .
H18A H 0.7659 0.0139 0.6584 0.100 Uiso 1 1 calc R . .
H18B H 0.8981 0.0024 0.7979 0.100 Uiso 1 1 calc R . .
H18C H 0.8798 0.0021 0.5638 0.100 Uiso 1 1 calc R . .
C19 C 1.1046(3) 0.06651(13) 0.8372(6) 0.0376(8) Uani 1 1 d . . .
O20 O 1.1032(3) 0.01642(10) 0.7970(6) 0.0746(11) Uani 1 1 d . . .
C21 C 1.2206(3) 0.09113(13) 0.9607(5) 0.0366(8) Uani 1 1 d . . .
H21A H 1.2794 0.0611 1.0083 0.055 Uiso 1 1 calc R . .
H21B H 1.2025 0.1110 1.0732 0.055 Uiso 1 1 calc R . .
H21C H 1.2554 0.1173 0.8808 0.055 Uiso 1 1 calc R . .
C22 C 0.4609(3) 0.31714(18) 0.2746(5) 0.0435(9) Uani 1 1 d . . .
O23 O 0.3536(2) 0.30377(14) 0.2184(4) 0.0574(8) Uani 1 1 d . . .
C24 C 0.4949(3) 0.37736(19) 0.2598(6) 0.0528(11) Uani 1 1 d . . .
H24A H 0.4270 0.3972 0.1731 0.079 Uiso 1 1 calc R . .
H24B H 0.5675 0.3798 0.2057 0.079 Uiso 1 1 calc R . .
H24C H 0.5124 0.3944 0.3911 0.079 Uiso 1 1 calc R . .
C25 C 0.4136(3) 0.19312(19) 0.2433(5) 0.0491(10) Uani 1 1 d . . .
H25A H 0.4224 0.1528 0.2269 0.074 Uiso 1 1 calc R . .
H25B H 0.3836 0.2105 0.1141 0.074 Uiso 1 1 calc R . .
H25C H 0.3553 0.2000 0.3252 0.074 Uiso 1 1 calc R . .


_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
Cu1 N13 1.907(2) . ?
Cu1 O2 1.909(2) . ?
Cu1 O17 1.911(2) . ?
Cu1 N6 1.914(2) . ?
O2 C3 1.279(4) . ?
C3 C4 1.419(4) . ?
C3 C18 1.497(4) . ?
C4 C5 1.415(4) . ?
C4 C19 1.475(4) . ?
C5 N6 1.302(4) . ?
C5 H5 0.9500 . ?
N6 C7 1.416(3) . ?
C7 C8 1.396(4) . ?
C7 C12 1.416(4) . ?
C8 C9 1.384(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(4) . ?
C11 H11 0.9500 . ?
C12 N13 1.422(3) . ?
N13 C14 1.312(4) . ?
C14 C15 1.426(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.424(5) . ?
C15 C22 1.480(5) . ?
C16 O17 1.272(4) . ?
C16 C25 1.502(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 O20 1.231(4) . ?
C19 C21 1.506(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 O23 1.222(5) . ?
C22 C24 1.501(6) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
N13 Cu1 O2 174.52(10) . . ?
N13 Cu1 O17 92.49(10) . . ?
O2 Cu1 O17 89.10(9) . . ?
N13 Cu1 N6 85.98(9) . . ?
O2 Cu1 N6 92.55(9) . . ?
O17 Cu1 N6 177.93(10) . . ?
C3 O2 Cu1 129.52(19) . . ?
O2 C3 C4 123.0(3) . . ?
O2 C3 C18 113.9(3) . . ?
C4 C3 C18 123.0(3) . . ?
C5 C4 C3 122.3(3) . . ?
C5 C4 C19 116.4(3) . . ?
C3 C4 C19 121.3(3) . . ?
N6 C5 C4 127.0(3) . . ?
N6 C5 H5 116.5 . . ?
C4 C5 H5 116.5 . . ?
C5 N6 C7 122.9(2) . . ?
C5 N6 Cu1 124.91(19) . . ?
C7 N6 Cu1 112.08(17) . . ?
C8 C7 C12 119.2(2) . . ?
C8 C7 N6 125.8(2) . . ?
C12 C7 N6 115.0(2) . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.2(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.4(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 119.6(2) . . ?
C11 C12 N13 125.8(2) . . ?
C7 C12 N13 114.5(2) . . ?
C14 N13 C12 121.8(3) . . ?
C14 N13 Cu1 125.9(2) . . ?
C12 N13 Cu1 112.34(17) . . ?
N13 C14 C15 126.1(3) . . ?
N13 C14 H14 117.0 . . ?
C15 C14 H14 117.0 . . ?
C16 C15 C14 122.2(3) . . ?
C16 C15 C22 121.1(3) . . ?
C14 C15 C22 116.7(3) . . ?
O17 C16 C15 123.3(3) . . ?
O17 C16 C25 113.4(3) . . ?
C15 C16 C25 123.4(3) . . ?
C16 O17 Cu1 129.8(2) . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O20 C19 C4 122.2(3) . . ?
O20 C19 C21 118.4(3) . . ?
C4 C19 C21 119.4(3) . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O23 C22 C15 122.4(4) . . ?
O23 C22 C24 118.6(3) . . ?
C15 C22 C24 119.0(3) . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C16 C25 H25A 109.5 . . ?
C16 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C16 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
O17 Cu1 O2 C3 171.3(3) . . . . ?
N6 Cu1 O2 C3 -7.4(3) . . . . ?
Cu1 O2 C3 C4 2.3(5) . . . . ?
Cu1 O2 C3 C18 -178.2(3) . . . . ?
O2 C3 C4 C5 5.2(5) . . . . ?
C18 C3 C4 C5 -174.3(4) . . . . ?
O2 C3 C4 C19 -175.0(3) . . . . ?
C18 C3 C4 C19 5.6(5) . . . . ?
C3 C4 C5 N6 -4.5(5) . . . . ?
C19 C4 C5 N6 175.6(3) . . . . ?
C4 C5 N6 C7 179.4(3) . . . . ?
C4 C5 N6 Cu1 -3.5(4) . . . . ?
N13 Cu1 N6 C5 -177.6(2) . . . . ?
O2 Cu1 N6 C5 7.7(2) . . . . ?
N13 Cu1 N6 C7 -0.22(18) . . . . ?
O2 Cu1 N6 C7 -174.93(18) . . . . ?
C5 N6 C7 C8 -1.8(4) . . . . ?
Cu1 N6 C7 C8 -179.2(2) . . . . ?
C5 N6 C7 C12 179.1(2) . . . . ?
Cu1 N6 C7 C12 1.7(3) . . . . ?
C12 C7 C8 C9 1.1(4) . . . . ?
N6 C7 C8 C9 -178.0(2) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
C8 C9 C10 C11 -1.0(4) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
C10 C11 C12 C7 0.9(4) . . . . ?
C10 C11 C12 N13 -178.8(3) . . . . ?
C8 C7 C12 C11 -1.7(4) . . . . ?
N6 C7 C12 C11 177.5(2) . . . . ?
C8 C7 C12 N13 178.1(2) . . . . ?
N6 C7 C12 N13 -2.7(3) . . . . ?
C11 C12 N13 C14 1.8(4) . . . . ?
C7 C12 N13 C14 -177.9(2) . . . . ?
C11 C12 N13 Cu1 -177.8(2) . . . . ?
C7 C12 N13 Cu1 2.5(3) . . . . ?
O17 Cu1 N13 C14 0.6(2) . . . . ?
N6 Cu1 N13 C14 179.2(2) . . . . ?
O17 Cu1 N13 C12 -179.83(18) . . . . ?
N6 Cu1 N13 C12 -1.22(17) . . . . ?
C12 N13 C14 C15 -177.7(3) . . . . ?
Cu1 N13 C14 C15 1.9(4) . . . . ?
N13 C14 C15 C16 -0.9(5) . . . . ?
N13 C14 C15 C22 177.5(3) . . . . ?
C14 C15 C16 O17 -3.9(5) . . . . ?
C22 C15 C16 O17 177.9(3) . . . . ?
C14 C15 C16 C25 176.3(3) . . . . ?
C22 C15 C16 C25 -2.0(5) . . . . ?
C15 C16 O17 Cu1 7.4(4) . . . . ?
C25 C16 O17 Cu1 -172.8(2) . . . . ?
N13 Cu1 O17 C16 -5.2(3) . . . . ?
O2 Cu1 O17 C16 169.5(3) . . . . ?
C5 C4 C19 O20 -166.1(4) . . . . ?
C3 C4 C19 O20 14.1(6) . . . . ?
C5 C4 C19 C21 11.8(5) . . . . ?
C3 C4 C19 C21 -168.1(3) . . . . ?
C16 C15 C22 O23 13.5(5) . . . . ?
C14 C15 C22 O23 -164.9(3) . . . . ?
C16 C15 C22 C24 -167.5(3) . . . . ?
C14 C15 C22 C24 14.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.943
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.954
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.075


# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 1.000 -0.057 132 28 ' '
2 0.500 0.500 -0.005 132 28 ' '
_platon_squeeze_details          
;
H2O/MeOH/EtOH mixture 
;

_database_code_depnum_ccdc_archive 'CCDC 995465'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cl202

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 N2 Ni O4, C H4 O'
_chemical_formula_sum            'C19 H22 N2 Ni O5'
_chemical_formula_weight         417.10

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'
Ni Ni 0.3393 1.1124 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   11.1128(5)
_cell_length_b                   23.9480(10)
_cell_length_c                   7.1300(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.599(5)
_cell_angle_gamma                90.00
_cell_volume                     1844.31(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2766
_cell_measurement_theta_min      3.0539
_cell_measurement_theta_max      25.2966

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    1.085
_exptl_absorpt_correction_T_min  0.76399
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '120 images, ΔΦ 1.5° '
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11832
_diffrn_reflns_av_R_equivalents  0.1074
_diffrn_reflns_av_sigmaI/netI    0.0889
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         25.35
_reflns_number_total             3349
_reflns_number_gt                2289
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;



_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0456P)²+1.5436P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3349
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1353
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.71771(5) 0.19499(2) 0.43173(8) 0.02202(16) Uani 1 1 d . . .
O2 O 0.8755(3) 0.18414(12) 0.5829(4) 0.0263(7) Uani 1 1 d . . .
C3 C 0.9597(4) 0.21944(19) 0.6578(6) 0.0245(10) Uani 1 1 d . . .
C4 C 0.9391(4) 0.27796(18) 0.6457(6) 0.0240(10) Uani 1 1 d . . .
C5 C 0.8238(4) 0.30000(19) 0.5452(6) 0.0241(10) Uani 1 1 d . . .
H5 H 0.8148 0.3394 0.5470 0.029 Uiso 1 1 calc R . .
N6 N 0.7280(3) 0.27138(14) 0.4497(5) 0.0214(8) Uani 1 1 d . . .
C7 C 0.6191(4) 0.29916(18) 0.3447(6) 0.0211(9) Uani 1 1 d . . .
C8 C 0.6025(4) 0.35581(18) 0.3206(6) 0.0268(10) Uani 1 1 d . . .
H8 H 0.6678 0.3807 0.3759 0.032 Uiso 1 1 calc R . .
C9 C 0.4908(4) 0.37654(19) 0.2158(6) 0.0265(10) Uani 1 1 d . . .
H9 H 0.4785 0.4157 0.2000 0.032 Uiso 1 1 calc R . .
C10 C 0.3961(4) 0.33950(19) 0.1334(6) 0.0271(11) Uani 1 1 d . . .
H10 H 0.3195 0.3538 0.0611 0.033 Uiso 1 1 calc R . .
C11 C 0.4114(4) 0.28309(19) 0.1545(6) 0.0263(10) Uani 1 1 d . . .
H11 H 0.3456 0.2586 0.0983 0.032 Uiso 1 1 calc R . .
C12 C 0.5239(4) 0.26163(18) 0.2590(6) 0.0229(10) Uani 1 1 d . . .
N13 N 0.5578(3) 0.20476(14) 0.2892(5) 0.0228(8) Uani 1 1 d . . .
C14 C 0.4786(4) 0.16465(18) 0.2250(6) 0.0244(10) Uani 1 1 d . . .
H14 H 0.3971 0.1758 0.1620 0.029 Uiso 1 1 calc R . .
C15 C 0.5018(4) 0.10672(18) 0.2394(6) 0.0234(10) Uani 1 1 d . . .
C16 C 0.6224(4) 0.08609(19) 0.3232(6) 0.0261(10) Uani 1 1 d . . .
O17 O 0.7123(3) 0.11816(12) 0.4006(4) 0.0269(7) Uani 1 1 d . . .
C18 C 1.0789(4) 0.19329(19) 0.7592(6) 0.0307(11) Uani 1 1 d . . .
H18A H 1.0659 0.1534 0.7783 0.046 Uiso 1 1 calc R . .
H18B H 1.1092 0.2113 0.8848 0.046 Uiso 1 1 calc R . .
H18C H 1.1400 0.1979 0.6813 0.046 Uiso 1 1 calc R . .
C19 C 1.0380(4) 0.31773(19) 0.7365(6) 0.0266(11) Uani 1 1 d . . .
O20 O 1.1469(3) 0.30384(14) 0.7875(4) 0.0358(8) Uani 1 1 d . . .
C21 C 1.0037(4) 0.37755(19) 0.7651(6) 0.0316(11) Uani 1 1 d . . .
H21A H 1.0744 0.3967 0.8486 0.047 Uiso 1 1 calc R . .
H21B H 0.9331 0.3784 0.8256 0.047 Uiso 1 1 calc R . .
H21C H 0.9813 0.3964 0.6398 0.047 Uiso 1 1 calc R . .
C22 C 0.3971(4) 0.0688(2) 0.1671(6) 0.0292(11) Uani 1 1 d . . .
O23 O 0.4013(3) 0.01859(14) 0.2047(5) 0.0424(9) Uani 1 1 d . . .
C24 C 0.2785(4) 0.09276(19) 0.0453(6) 0.0325(11) Uani 1 1 d . . .
H24A H 0.2212 0.0623 -0.0058 0.049 Uiso 1 1 calc R . .
H24B H 0.2969 0.1141 -0.0620 0.049 Uiso 1 1 calc R . .
H24C H 0.2406 0.1175 0.1247 0.049 Uiso 1 1 calc R . .
C25 C 0.6571(5) 0.02606(19) 0.3220(8) 0.0409(13) Uani 1 1 d . . .
H25A H 0.7474 0.0227 0.3457 0.061 Uiso 1 1 calc R . .
H25B H 0.6187 0.0097 0.1962 0.061 Uiso 1 1 calc R . .
H25C H 0.6282 0.0062 0.4233 0.061 Uiso 1 1 calc R . .
O101 O 0.8180(4) 0.04359(18) 0.9316(6) 0.0676(13) Uani 1 1 d . . .
H101 H 0.7526 0.0252 0.8920 0.101 Uiso 1 1 calc R . .
C102 C 0.8957(6) 0.0403(3) 0.7857(9) 0.072(2) Uani 1 1 d . . .
H10A H 0.8923 0.0761 0.7181 0.108 Uiso 1 1 calc R . .
H10B H 0.8639 0.0107 0.6925 0.108 Uiso 1 1 calc R . .
H10C H 0.9816 0.0320 0.8515 0.108 Uiso 1 1 calc R . .


_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
Ni1 N6 1.836(3) . ?
Ni1 N13 1.843(3) . ?
Ni1 O2 1.848(3) . ?
Ni1 O17 1.852(3) . ?
O2 C3 1.281(5) . ?
C3 C4 1.419(6) . ?
C3 C18 1.490(6) . ?
C4 C5 1.415(6) . ?
C4 C19 1.483(6) . ?
C5 N6 1.314(5) . ?
C5 H5 0.9500 . ?
N6 C7 1.429(5) . ?
C7 C8 1.374(6) . ?
C7 C12 1.412(6) . ?
C8 C9 1.382(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.395(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.366(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.395(6) . ?
C11 H11 0.9500 . ?
C12 N13 1.416(5) . ?
N13 C14 1.311(5) . ?
C14 C15 1.410(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.422(6) . ?
C15 C22 1.471(6) . ?
C16 O17 1.278(5) . ?
C16 C25 1.489(6) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 O20 1.225(5) . ?
C19 C21 1.509(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 O23 1.230(5) . ?
C22 C24 1.510(6) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
O101 C102 1.501(7) . ?
O101 H101 0.8400 . ?
C102 H10A 0.9800 . ?
C102 H10B 0.9800 . ?
C102 H10C 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
N6 Ni1 N13 87.04(15) . . ?
N6 Ni1 O2 93.68(14) . . ?
N13 Ni1 O2 177.67(14) . . ?
N6 Ni1 O17 176.31(14) . . ?
N13 Ni1 O17 93.45(14) . . ?
O2 Ni1 O17 85.98(13) . . ?
C3 O2 Ni1 130.6(3) . . ?
O2 C3 C4 122.3(4) . . ?
O2 C3 C18 113.8(4) . . ?
C4 C3 C18 123.8(4) . . ?
C5 C4 C3 120.9(4) . . ?
C5 C4 C19 118.1(4) . . ?
C3 C4 C19 121.0(4) . . ?
N6 C5 C4 126.5(4) . . ?
N6 C5 H5 116.8 . . ?
C4 C5 H5 116.8 . . ?
C5 N6 C7 120.8(4) . . ?
C5 N6 Ni1 125.9(3) . . ?
C7 N6 Ni1 113.3(3) . . ?
C8 C7 C12 120.6(4) . . ?
C8 C7 N6 126.6(4) . . ?
C12 C7 N6 112.7(4) . . ?
C7 C8 C9 119.9(4) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 119.5(4) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 121.4(4) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 119.7(4) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C7 118.9(4) . . ?
C11 C12 N13 127.5(4) . . ?
C7 C12 N13 113.6(4) . . ?
C14 N13 C12 121.3(4) . . ?
C14 N13 Ni1 125.5(3) . . ?
C12 N13 Ni1 113.2(3) . . ?
N13 C14 C15 126.8(4) . . ?
N13 C14 H14 116.6 . . ?
C15 C14 H14 116.6 . . ?
C14 C15 C16 120.7(4) . . ?
C14 C15 C22 117.8(4) . . ?
C16 C15 C22 121.5(4) . . ?
O17 C16 C15 122.4(4) . . ?
O17 C16 C25 113.9(4) . . ?
C15 C16 C25 123.6(4) . . ?
C16 O17 Ni1 130.5(3) . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O20 C19 C4 122.3(4) . . ?
O20 C19 C21 118.8(4) . . ?
C4 C19 C21 118.9(4) . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O23 C22 C15 122.7(4) . . ?
O23 C22 C24 118.7(4) . . ?
C15 C22 C24 118.5(4) . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C16 C25 H25A 109.5 . . ?
C16 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C16 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C102 O101 H101 109.5 . . ?
O101 C102 H10A 109.5 . . ?
O101 C102 H10B 109.5 . . ?
H10A C102 H10B 109.5 . . ?
O101 C102 H10C 109.5 . . ?
H10A C102 H10C 109.5 . . ?
H10B C102 H10C 109.5 . . ?

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
N6 Ni1 O2 C3 -3.9(4) . . . . ?
O17 Ni1 O2 C3 172.4(4) . . . . ?
Ni1 O2 C3 C4 4.9(6) . . . . ?
Ni1 O2 C3 C18 -175.7(3) . . . . ?
O2 C3 C4 C5 -1.4(7) . . . . ?
C18 C3 C4 C5 179.3(4) . . . . ?
O2 C3 C4 C19 179.1(4) . . . . ?
C18 C3 C4 C19 -0.2(7) . . . . ?
C3 C4 C5 N6 -2.6(7) . . . . ?
C19 C4 C5 N6 176.9(4) . . . . ?
C4 C5 N6 C7 -176.3(4) . . . . ?
C4 C5 N6 Ni1 2.9(6) . . . . ?
N13 Ni1 N6 C5 177.7(4) . . . . ?
O2 Ni1 N6 C5 0.0(4) . . . . ?
N13 Ni1 N6 C7 -3.0(3) . . . . ?
O2 Ni1 N6 C7 179.2(3) . . . . ?
C5 N6 C7 C8 3.9(6) . . . . ?
Ni1 N6 C7 C8 -175.4(3) . . . . ?
C5 N6 C7 C12 -177.1(4) . . . . ?
Ni1 N6 C7 C12 3.6(4) . . . . ?
C12 C7 C8 C9 1.7(6) . . . . ?
N6 C7 C8 C9 -179.4(4) . . . . ?
C7 C8 C9 C10 -0.8(7) . . . . ?
C8 C9 C10 C11 0.2(7) . . . . ?
C9 C10 C11 C12 -0.6(7) . . . . ?
C10 C11 C12 C7 1.4(6) . . . . ?
C10 C11 C12 N13 -177.3(4) . . . . ?
C8 C7 C12 C11 -2.0(6) . . . . ?
N6 C7 C12 C11 179.0(4) . . . . ?
C8 C7 C12 N13 176.9(4) . . . . ?
N6 C7 C12 N13 -2.1(5) . . . . ?
C11 C12 N13 C14 -3.7(7) . . . . ?
C7 C12 N13 C14 177.6(4) . . . . ?
C11 C12 N13 Ni1 178.5(4) . . . . ?
C7 C12 N13 Ni1 -0.2(4) . . . . ?
N6 Ni1 N13 C14 -175.9(4) . . . . ?
O17 Ni1 N13 C14 7.8(4) . . . . ?
N6 Ni1 N13 C12 1.8(3) . . . . ?
O17 Ni1 N13 C12 -174.5(3) . . . . ?
C12 N13 C14 C15 177.6(4) . . . . ?
Ni1 N13 C14 C15 -4.8(6) . . . . ?
N13 C14 C15 C16 -2.9(7) . . . . ?
N13 C14 C15 C22 176.5(4) . . . . ?
C14 C15 C16 O17 5.0(6) . . . . ?
C22 C15 C16 O17 -174.3(4) . . . . ?
C14 C15 C16 C25 -172.4(4) . . . . ?
C22 C15 C16 C25 8.3(7) . . . . ?
C15 C16 O17 Ni1 0.8(6) . . . . ?
C25 C16 O17 Ni1 178.4(3) . . . . ?
N13 Ni1 O17 C16 -6.1(4) . . . . ?
O2 Ni1 O17 C16 171.6(4) . . . . ?
C5 C4 C19 O20 -163.2(4) . . . . ?
C3 C4 C19 O20 16.3(6) . . . . ?
C5 C4 C19 C21 16.1(6) . . . . ?
C3 C4 C19 C21 -164.4(4) . . . . ?
C14 C15 C22 O23 -166.0(4) . . . . ?
C16 C15 C22 O23 13.4(7) . . . . ?
C14 C15 C22 C24 12.6(6) . . . . ?
C16 C15 C22 C24 -168.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.102

_database_code_depnum_ccdc_archive 'CCDC 995466'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_nn150
_audit_creation_date             2009-04-01
_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H26 Cu N2 O8'
_chemical_formula_sum            'C22 H26 Cu N2 O8'
_chemical_formula_weight         510.00

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'
Cu Cu 0.3201 1.2651 '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      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                   6.74840(10)
_cell_length_b                   21.9827(3)
_cell_length_c                   16.0526(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.1720(10)
_cell_angle_gamma                90
_cell_volume                     2298.37(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    10333
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       rod
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_F_000             1060
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.017
_exptl_crystal_size_min          0.012
_exptl_absorpt_coefficient_mu    1.000
_shelx_estimated_absorpt_T_min   0.696
_shelx_estimated_absorpt_T_max   0.988
_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      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   55.00
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD; rotation images; thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            19693
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.197
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5266
_reflns_number_gt                3889
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
;
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  PLATON

_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)+(0.0489P)²+1.0370P]
 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         5266
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1067
_refine_ls_wR_factor_gt          0.0960
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
Cu1 Cu 0.22362(4) 0.39574(2) 0.50344(2) 0.03425(11) Uani 1 1 d . . . . .
O2 O 0.2885(3) 0.33815(7) 0.59649(10) 0.0393(4) Uani 1 1 d . . . . .
C3 C 0.3657(3) 0.34870(11) 0.67533(14) 0.0347(5) Uani 1 1 d . . . . .
C4 C 0.4157(4) 0.40740(11) 0.71288(14) 0.0354(5) Uani 1 1 d . . . . .
C5 C 0.3885(4) 0.46027(11) 0.66265(14) 0.0330(5) Uani 1 1 d . . . . .
H5 H 0.4272 0.4976 0.6923 0.040 Uiso 1 1 calc R U . . .
N6 N 0.3141(3) 0.46332(8) 0.57799(11) 0.0319(4) Uani 1 1 d . . . . .
C7 C 0.2904(3) 0.51950(10) 0.53323(14) 0.0317(5) Uani 1 1 d . . . . .
C8 C 0.3502(4) 0.57603(11) 0.56912(15) 0.0374(5) Uani 1 1 d . . . . .
H8 H 0.4148 0.5793 0.6291 0.045 Uiso 1 1 calc R U . . .
C9 C 0.3166(4) 0.62774(11) 0.51824(16) 0.0412(6) Uani 1 1 d . . . . .
H9 H 0.3575 0.6664 0.5434 0.049 Uiso 1 1 calc R U . . .
C10 C 0.2235(4) 0.62333(11) 0.43075(16) 0.0418(6) Uani 1 1 d . . . . .
H10 H 0.1995 0.6590 0.3961 0.050 Uiso 1 1 calc R U . . .
C11 C 0.1656(4) 0.56732(11) 0.39369(15) 0.0382(5) Uani 1 1 d . . . . .
H11 H 0.1043 0.5645 0.3334 0.046 Uiso 1 1 calc R U . . .
C12 C 0.1960(3) 0.51494(10) 0.44375(14) 0.0316(5) Uani 1 1 d . . . . .
N13 N 0.1459(3) 0.45512(8) 0.41383(11) 0.0318(4) Uani 1 1 d . . . . .
C14 C 0.0475(4) 0.44333(11) 0.33336(14) 0.0349(5) Uani 1 1 d . . . . .
H14 H 0.0077 0.4775 0.2966 0.042 Uiso 1 1 calc R U . . .
C15 C -0.0054(4) 0.38604(11) 0.29563(14) 0.0351(5) Uani 1 1 d . . . . .
C16 C 0.0492(3) 0.33144(11) 0.34457(14) 0.0344(5) Uani 1 1 d . . . . .
O17 O 0.1427(3) 0.32987(7) 0.42377(10) 0.0406(4) Uani 1 1 d . . . . .
O18 O 0.4107(3) 0.30138(7) 0.72865(10) 0.0404(4) Uani 1 1 d . . . . .
C19 C 0.4971(4) 0.41465(11) 0.80701(15) 0.0410(6) Uani 1 1 d . . . . .
O20 O 0.4759(4) 0.38038(9) 0.86209(12) 0.0627(6) Uani 1 1 d . . . . .
O21 O 0.6001(3) 0.46748(8) 0.82593(10) 0.0505(5) Uani 1 1 d . . . . .
C22 C -0.1205(4) 0.39004(12) 0.20347(17) 0.0449(6) Uani 1 1 d . . . . .
O23 O -0.1384(3) 0.33812(8) 0.15957(10) 0.0515(5) Uani 1 1 d . . . . .
O24 O -0.1919(4) 0.43695(9) 0.16994(13) 0.0776(8) Uani 1 1 d . . . . .
O25 O -0.0014(3) 0.27862(7) 0.30463(10) 0.0383(4) Uani 1 1 d . . . . .
C26 C 0.3544(4) 0.24142(11) 0.69231(16) 0.0459(6) Uani 1 1 d . . . . .
H26A H 0.4001 0.2361 0.6390 0.055 Uiso 1 1 calc R U . . .
H26B H 0.2037 0.2360 0.6780 0.055 Uiso 1 1 calc R U . . .
C27 C 0.4591(4) 0.19620(12) 0.75948(18) 0.0486(6) Uani 1 1 d . . . . .
H27A H 0.6082 0.2000 0.7697 0.073 Uiso 1 1 calc R U . . .
H27B H 0.4165 0.1550 0.7393 0.073 Uiso 1 1 calc R U . . .
H27C H 0.4209 0.2041 0.8133 0.073 Uiso 1 1 calc R U . . .
C28 C 0.6547(6) 0.48560(15) 0.91573(18) 0.0717(10) Uani 1 1 d . . . . .
H28A H 0.7513 0.4557 0.9507 0.086 Uiso 1 1 calc R U . . .
H28B H 0.5302 0.4870 0.9374 0.086 Uiso 1 1 calc R U . . .
C29 C 0.7501(6) 0.54543(15) 0.9235(2) 0.0805(11) Uani 1 1 d . . . . .
H29A H 0.8765 0.5434 0.9043 0.121 Uiso 1 1 calc R U . . .
H29B H 0.7831 0.5587 0.9838 0.121 Uiso 1 1 calc R U . . .
H29C H 0.6552 0.5745 0.8874 0.121 Uiso 1 1 calc R U . . .
C30 C -0.2460(6) 0.34359(14) 0.06813(18) 0.0692(10) Uani 1 1 d . . . . .
H30A H -0.3826 0.3622 0.0619 0.083 Uiso 1 1 calc R U . . .
H30B H -0.1668 0.3700 0.0387 0.083 Uiso 1 1 calc R U . . .
C31 C -0.2693(6) 0.28379(15) 0.0293(2) 0.0701(9) Uani 1 1 d . . . . .
H31A H -0.1339 0.2650 0.0376 0.105 Uiso 1 1 calc R U . . .
H31B H -0.3356 0.2874 -0.0326 0.105 Uiso 1 1 calc R U . . .
H31C H -0.3542 0.2585 0.0566 0.105 Uiso 1 1 calc R U . . .
C32 C 0.0599(5) 0.22352(11) 0.35641(16) 0.0459(6) Uani 1 1 d . . . . .
H32A H 0.0117 0.2254 0.4095 0.055 Uiso 1 1 calc R U . . .
H32B H 0.2113 0.2195 0.3732 0.055 Uiso 1 1 calc R U . . .
C33 C -0.0353(4) 0.17076(12) 0.30241(19) 0.0538(7) Uani 1 1 d . . . . .
H33A H -0.1850 0.1751 0.2867 0.081 Uiso 1 1 calc R U . . .
H33B H 0.0036 0.1330 0.3351 0.081 Uiso 1 1 calc R U . . .
H33C H 0.0130 0.1695 0.2499 0.081 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
Cu1 N6 1.9051(18) . ?
Cu1 N13 1.9114(18) . ?
Cu1 O17 1.9143(16) . ?
Cu1 O2 1.9191(15) . ?
O2 C3 1.258(3) . ?
C3 O18 1.331(3) . ?
C3 C4 1.427(3) . ?
C4 C5 1.399(3) . ?
C4 C19 1.475(3) . ?
C5 N6 1.321(3) . ?
C5 H5 0.9500 . ?
N6 C7 1.417(3) . ?
C7 C8 1.385(3) . ?
C7 C12 1.414(3) . ?
C8 C9 1.383(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.379(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 N13 1.410(3) . ?
N13 C14 1.314(3) . ?
C14 C15 1.403(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.429(3) . ?
C15 C22 1.483(3) . ?
C16 O17 1.263(3) . ?
C16 O25 1.327(3) . ?
O18 C26 1.451(3) . ?
C19 O20 1.198(3) . ?
C19 O21 1.347(3) . ?
O21 C28 1.447(3) . ?
C22 O24 1.204(3) . ?
C22 O23 1.330(3) . ?
O23 C30 1.462(3) . ?
O25 C32 1.466(3) . ?
C26 C27 1.500(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.456(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.446(4) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.489(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 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
N6 Cu1 N13 85.40(8) . . ?
N6 Cu1 O17 176.32(8) . . ?
N13 Cu1 O17 92.27(7) . . ?
N6 Cu1 O2 93.16(7) . . ?
N13 Cu1 O2 176.40(7) . . ?
O17 Cu1 O2 89.32(7) . . ?
C3 O2 Cu1 127.70(15) . . ?
O2 C3 O18 117.9(2) . . ?
O2 C3 C4 125.6(2) . . ?
O18 C3 C4 116.5(2) . . ?
C5 C4 C3 121.8(2) . . ?
C5 C4 C19 117.3(2) . . ?
C3 C4 C19 120.9(2) . . ?
N6 C5 C4 126.3(2) . . ?
N6 C5 H5 116.8 . . ?
C4 C5 H5 116.8 . . ?
C5 N6 C7 121.86(19) . . ?
C5 N6 Cu1 125.41(16) . . ?
C7 N6 Cu1 112.72(14) . . ?
C8 C7 C12 119.4(2) . . ?
C8 C7 N6 126.1(2) . . ?
C12 C7 N6 114.48(19) . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.2(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.6(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 N13 126.2(2) . . ?
C11 C12 C7 119.2(2) . . ?
N13 C12 C7 114.59(19) . . ?
C14 N13 C12 122.20(19) . . ?
C14 N13 Cu1 125.00(16) . . ?
C12 N13 Cu1 112.73(14) . . ?
N13 C14 C15 127.4(2) . . ?
N13 C14 H14 116.3 . . ?
C15 C14 H14 116.3 . . ?
C14 C15 C16 121.1(2) . . ?
C14 C15 C22 112.7(2) . . ?
C16 C15 C22 126.2(2) . . ?
O17 C16 O25 117.4(2) . . ?
O17 C16 C15 124.4(2) . . ?
O25 C16 C15 118.2(2) . . ?
C16 O17 Cu1 129.19(15) . . ?
C3 O18 C26 117.37(18) . . ?
O20 C19 O21 122.0(2) . . ?
O20 C19 C4 127.1(2) . . ?
O21 C19 C4 110.9(2) . . ?
C19 O21 C28 116.3(2) . . ?
O24 C22 O23 121.9(2) . . ?
O24 C22 C15 122.7(2) . . ?
O23 C22 C15 115.4(2) . . ?
C22 O23 C30 114.4(2) . . ?
C16 O25 C32 116.76(18) . . ?
O18 C26 C27 106.8(2) . . ?
O18 C26 H26A 110.4 . . ?
C27 C26 H26A 110.4 . . ?
O18 C26 H26B 110.4 . . ?
C27 C26 H26B 110.4 . . ?
H26A C26 H26B 108.6 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O21 C28 C29 109.0(3) . . ?
O21 C28 H28A 109.9 . . ?
C29 C28 H28A 109.9 . . ?
O21 C28 H28B 109.9 . . ?
C29 C28 H28B 109.9 . . ?
H28A C28 H28B 108.3 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 O23 109.1(2) . . ?
C31 C30 H30A 109.9 . . ?
O23 C30 H30A 109.9 . . ?
C31 C30 H30B 109.9 . . ?
O23 C30 H30B 109.9 . . ?
H30A C30 H30B 108.3 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O25 C32 C33 107.4(2) . . ?
O25 C32 H32A 110.2 . . ?
C33 C32 H32A 110.2 . . ?
O25 C32 H32B 110.2 . . ?
C33 C32 H32B 110.2 . . ?
H32A C32 H32B 108.5 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

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
Cu1 O2 C3 O18 -175.74(15) . . . . ?
Cu1 O2 C3 C4 2.3(3) . . . . ?
O2 C3 C4 C5 -2.4(4) . . . . ?
O18 C3 C4 C5 175.7(2) . . . . ?
O2 C3 C4 C19 177.2(2) . . . . ?
O18 C3 C4 C19 -4.8(3) . . . . ?
C3 C4 C5 N6 0.9(4) . . . . ?
C19 C4 C5 N6 -178.6(2) . . . . ?
C4 C5 N6 C7 179.2(2) . . . . ?
C4 C5 N6 Cu1 0.4(3) . . . . ?
C5 N6 C7 C8 4.0(4) . . . . ?
Cu1 N6 C7 C8 -177.04(19) . . . . ?
C5 N6 C7 C12 -176.0(2) . . . . ?
Cu1 N6 C7 C12 3.0(2) . . . . ?
C12 C7 C8 C9 0.6(3) . . . . ?
N6 C7 C8 C9 -179.4(2) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
C9 C10 C11 C12 1.3(4) . . . . ?
C10 C11 C12 N13 -179.3(2) . . . . ?
C10 C11 C12 C7 -1.0(4) . . . . ?
C8 C7 C12 C11 0.1(3) . . . . ?
N6 C7 C12 C11 -179.9(2) . . . . ?
C8 C7 C12 N13 178.57(19) . . . . ?
N6 C7 C12 N13 -1.4(3) . . . . ?
C11 C12 N13 C14 -5.4(4) . . . . ?
C7 C12 N13 C14 176.2(2) . . . . ?
C11 C12 N13 Cu1 177.58(19) . . . . ?
C7 C12 N13 Cu1 -0.8(2) . . . . ?
C12 N13 C14 C15 178.0(2) . . . . ?
Cu1 N13 C14 C15 -5.3(3) . . . . ?
N13 C14 C15 C16 -0.9(4) . . . . ?
N13 C14 C15 C22 178.7(2) . . . . ?
C14 C15 C16 O17 1.6(4) . . . . ?
C22 C15 C16 O17 -177.9(2) . . . . ?
C14 C15 C16 O25 -178.5(2) . . . . ?
C22 C15 C16 O25 1.9(4) . . . . ?
O25 C16 O17 Cu1 -175.59(14) . . . . ?
C15 C16 O17 Cu1 4.3(4) . . . . ?
O2 C3 O18 C26 -4.0(3) . . . . ?
C4 C3 O18 C26 177.8(2) . . . . ?
C5 C4 C19 O20 156.1(3) . . . . ?
C3 C4 C19 O20 -23.4(4) . . . . ?
C5 C4 C19 O21 -22.5(3) . . . . ?
C3 C4 C19 O21 158.0(2) . . . . ?
O20 C19 O21 C28 -9.9(4) . . . . ?
C4 C19 O21 C28 168.8(3) . . . . ?
C14 C15 C22 O24 -12.6(4) . . . . ?
C16 C15 C22 O24 167.0(3) . . . . ?
C14 C15 C22 O23 166.8(2) . . . . ?
C16 C15 C22 O23 -13.7(4) . . . . ?
O24 C22 O23 C30 1.5(4) . . . . ?
C15 C22 O23 C30 -177.9(3) . . . . ?
O17 C16 O25 C32 -1.0(3) . . . . ?
C15 C16 O25 C32 179.1(2) . . . . ?
C3 O18 C26 C27 168.4(2) . . . . ?
C19 O21 C28 C29 -175.7(3) . . . . ?
C22 O23 C30 C31 -175.6(3) . . . . ?
C16 O25 C32 C33 172.8(2) . . . . ?

_refine_diff_density_max         0.559
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.059

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 995467'
