# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1a_14srv044
_audit_creation_date             2014-02-21
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4773)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
1-[2-(1H-imidazol-4-yl)ethyl]-3-(4-methylphenyl)urea 
;
_chemical_formula_moiety         'C13 H16 N4 O'
_chemical_formula_sum            'C13 H16 N4 O'
_chemical_formula_weight         244.30
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H16 N4 O1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n 21 a'
_space_group_name_Hall           'P -2ac -2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'
3 'x+1/2, y, -z+1/2'
4 '-x+1/2, y+1/2, z+1/2'

_cell_length_a                   9.2520(3)
_cell_length_b                   10.1218(3)
_cell_length_c                   13.0422(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1221.37(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3644
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.5600
_cell_measurement_theta_min      2.5360
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14717
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.55
_diffrn_ambient_temperature      120.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0594118000
_diffrn_orient_matrix_UB_12      -0.0183020000
_diffrn_orient_matrix_UB_13      0.0312962000
_diffrn_orient_matrix_UB_21      -0.0394268000
_diffrn_orient_matrix_UB_22      0.0188100000
_diffrn_orient_matrix_UB_23      0.0442843000
_diffrn_orient_matrix_UB_31      -0.0280974000
_diffrn_orient_matrix_UB_32      -0.0650137000
_diffrn_orient_matrix_UB_33      0.0040139000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'sealed tube'
_diffrn_special_details          ?
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3198
_reflns_number_total             3557
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(14)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3557
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.0900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1000
_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. 
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.32931(11) 0.68411(15) 0.75124(8) 0.0222(2) Uani 1 d . . .
N1 N 0.28192(15) 0.86738(15) 0.28032(10) 0.0193(3) Uani 1 d . . .
N2 N 0.50877(15) 0.85203(14) 0.33269(10) 0.0192(3) Uani 1 d . . .
N3 N 0.54080(14) 0.68872(15) 0.66316(9) 0.0174(3) Uani 1 d . . .
N4 N 0.54487(14) 0.66757(14) 0.83729(9) 0.0169(3) Uani 1 d . . .
C1 C 0.42176(18) 0.85851(17) 0.25317(11) 0.0192(3) Uani 1 d . . .
C2 C 0.27859(18) 0.86689(17) 0.38601(11) 0.0206(3) Uani 1 d . . .
C3 C 0.41837(16) 0.85713(15) 0.41757(10) 0.0165(3) Uani 1 d . . .
C4 C 0.47488(18) 0.84669(15) 0.52485(11) 0.0192(3) Uani 1 d . . .
C5 C 0.47537(17) 0.70314(15) 0.56275(11) 0.0172(3) Uani 1 d . . .
C6 C 0.46271(15) 0.68042(17) 0.74999(11) 0.0149(2) Uani 1 d . . .
C7 C 0.49085(16) 0.63267(15) 0.93453(11) 0.0154(3) Uani 1 d . . .
C8 C 0.36370(16) 0.68604(17) 0.97462(11) 0.0171(3) Uani 1 d . . .
C9 C 0.31598(18) 0.64766(15) 1.07103(12) 0.0195(3) Uani 1 d . . .
C10 C 0.39336(18) 0.55851(16) 1.13086(11) 0.0207(3) Uani 1 d . . .
C11 C 0.52111(18) 0.50814(16) 1.09127(12) 0.0211(3) Uani 1 d . . .
C12 C 0.56992(17) 0.54388(16) 0.99435(11) 0.0187(3) Uani 1 d . . .
C13 C 0.3408(3) 0.5199(2) 1.23630(14) 0.0310(4) Uani 1 d . . .
H1A H 0.4511(19) 0.8563(19) 0.1822(14) 0.018(4) Uiso 1 d . . .
H1 H 0.206(3) 0.872(2) 0.2387(14) 0.034(6) Uiso 1 d . . .
H2 H 0.189(2) 0.877(2) 0.4231(14) 0.026(5) Uiso 1 d . . .
H3 H 0.632(2) 0.679(2) 0.6674(13) 0.023(5) Uiso 1 d . . .
H4 H 0.639(2) 0.6581(19) 0.8276(13) 0.018(5) Uiso 1 d . . .
H4A H 0.574(2) 0.887(2) 0.5287(15) 0.032(5) Uiso 1 d . . .
H4B H 0.418(2) 0.898(2) 0.5731(14) 0.024(5) Uiso 1 d . . .
H5A H 0.5264(19) 0.6485(17) 0.5148(13) 0.010(4) Uiso 1 d . . .
H5B H 0.374(2) 0.672(2) 0.5667(13) 0.019(4) Uiso 1 d . . .
H8 H 0.306(2) 0.7504(18) 0.9405(14) 0.016(4) Uiso 1 d . . .
H9 H 0.231(2) 0.684(2) 1.0953(13) 0.026(5) Uiso 1 d . . .
H11 H 0.579(2) 0.446(2) 1.1277(16) 0.036(6) Uiso 1 d . . .
H12 H 0.6594(19) 0.5080(17) 0.9681(12) 0.012(4) Uiso 1 d . . .
H13A H 0.262(4) 0.581(3) 1.263(2) 0.079(10) Uiso 1 d . . .
H13B H 0.311(4) 0.434(4) 1.2396(18) 0.066(9) Uiso 1 d . . .
H13C H 0.416(4) 0.542(3) 1.285(3) 0.075(9) Uiso 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.2349(17) . ?
N1 C1 1.344(2) . ?
N1 C2 1.3788(19) . ?
N1 H1 0.89(2) . ?
N2 C1 1.315(2) . ?
N2 C3 1.3884(19) . ?
N3 C5 1.4502(18) . ?
N3 C6 1.3458(17) . ?
N3 H3 0.85(2) . ?
N4 C6 1.3752(17) . ?
N4 C7 1.4082(18) . ?
N4 H4 0.881(19) . ?
C1 H1A 0.965(18) . ?
C2 C3 1.361(2) . ?
C2 H2 0.96(2) . ?
C3 C4 1.4973(19) . ?
C4 C5 1.535(2) . ?
C4 H4A 1.00(2) . ?
C4 H4B 0.97(2) . ?
C5 H5A 0.959(18) . ?
C5 H5B 0.989(19) . ?
C7 C8 1.396(2) . ?
C7 C12 1.397(2) . ?
C8 C9 1.388(2) . ?
C8 H8 0.953(19) . ?
C9 C10 1.391(2) . ?
C9 H9 0.93(2) . ?
C10 C11 1.387(2) . ?
C10 C13 1.510(2) . ?
C11 C12 1.390(2) . ?
C11 H11 0.95(2) . ?
C12 H12 0.967(17) . ?
C13 H13A 1.01(4) . ?
C13 H13B 0.91(4) . ?
C13 H13C 0.97(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 106.53(13) . . ?
C1 N1 H1 127.1(14) . . ?
C2 N1 H1 126.3(14) . . ?
C1 N2 C3 104.97(12) . . ?
C5 N3 H3 118.9(12) . . ?
C6 N3 C5 122.82(12) . . ?
C6 N3 H3 118.1(12) . . ?
C6 N4 C7 124.98(13) . . ?
C6 N4 H4 115.8(11) . . ?
C7 N4 H4 116.8(12) . . ?
N1 C1 H1A 121.6(11) . . ?
N2 C1 N1 112.64(13) . . ?
N2 C1 H1A 125.7(11) . . ?
N1 C2 H2 121.4(11) . . ?
C3 C2 N1 106.35(13) . . ?
C3 C2 H2 132.2(11) . . ?
N2 C3 C4 122.15(13) . . ?
C2 C3 N2 109.51(12) . . ?
C2 C3 C4 128.29(13) . . ?
C3 C4 C5 111.64(13) . . ?
C3 C4 H4A 109.7(11) . . ?
C3 C4 H4B 112.2(12) . . ?
C5 C4 H4A 111.3(13) . . ?
C5 C4 H4B 107.3(12) . . ?
H4A C4 H4B 104.5(17) . . ?
N3 C5 C4 112.79(12) . . ?
N3 C5 H5A 109.0(10) . . ?
N3 C5 H5B 108.5(10) . . ?
C4 C5 H5A 109.7(10) . . ?
C4 C5 H5B 108.2(12) . . ?
H5A C5 H5B 108.6(15) . . ?
O1 C6 N3 123.08(13) . . ?
O1 C6 N4 122.98(13) . . ?
N3 C6 N4 113.94(12) . . ?
C8 C7 N4 122.64(14) . . ?
C8 C7 C12 118.75(14) . . ?
C12 C7 N4 118.59(14) . . ?
C7 C8 H8 124.2(11) . . ?
C9 C8 C7 119.93(15) . . ?
C9 C8 H8 115.9(11) . . ?
C8 C9 C10 121.73(15) . . ?
C8 C9 H9 118.2(12) . . ?
C10 C9 H9 120.1(12) . . ?
C9 C10 C13 120.83(16) . . ?
C11 C10 C9 117.91(14) . . ?
C11 C10 C13 121.24(16) . . ?
C10 C11 C12 121.31(15) . . ?
C10 C11 H11 122.3(13) . . ?
C12 C11 H11 116.4(13) . . ?
C7 C12 H12 119.5(10) . . ?
C11 C12 C7 120.34(15) . . ?
C11 C12 H12 120.1(10) . . ?
C10 C13 H13A 113.1(18) . . ?
C10 C13 H13B 112.7(16) . . ?
C10 C13 H13C 108(2) . . ?
H13A C13 H13B 110(3) . . ?
H13A C13 H13C 99(3) . . ?
H13B C13 H13C 114(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.89(2) 2.06(2) 2.9297(18) 167(2) 3_455
N3 H3 O1 0.85(2) 2.11(2) 2.8937(16) 152.5(17) 3_556
N4 H4 O1 0.881(19) 2.059(19) 2.8787(16) 154.3(17) 3_556

_database_code_depnum_ccdc_archive 'CCDC 1016071'
#######################################################################
#
#                 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_sj4_cucl2
_audit_creation_date             2014-07-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C52 H64 Cl Cu N16 O4, Cl'
_chemical_formula_sum            'C52 H64 Cl2 Cu N16 O4'
_chemical_formula_weight         1111.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         C52N16O4CuCl2H64
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'
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'
Cl Cl 0.1484 0.1585 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           85
_space_group_name_H-M_alt        'P 4/n'
_space_group_name_Hall           '-P 4a'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/2, x, z'
'-x+1/2, -y+1/2, z'
'y, -x+1/2, z'
'-x, -y, -z'
'y-1/2, -x, -z'
'x-1/2, y-1/2, -z'
'-y, x-1/2, -z'

_cell_length_a                   19.9812(6)
_cell_length_b                   19.9812(6)
_cell_length_c                   6.9508(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2775.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5879
_cell_measurement_temperature    120
_cell_measurement_theta_max      32.3713
_cell_measurement_theta_min      2.0343
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.549
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1166
_exptl_crystal_size_max          0.2111
_exptl_crystal_size_mid          0.1334
_exptl_crystal_size_min          0.104
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1003
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            39619
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         2.038
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 16.1511
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0325836000
_diffrn_orient_matrix_UB_12      -0.0064798000
_diffrn_orient_matrix_UB_13      0.0360440000
_diffrn_orient_matrix_UB_21      -0.0132974000
_diffrn_orient_matrix_UB_22      -0.0035642000
_diffrn_orient_matrix_UB_23      0.0940273000
_diffrn_orient_matrix_UB_31      -0.0047209000
_diffrn_orient_matrix_UB_32      -0.0347176000
_diffrn_orient_matrix_UB_33      -0.0163960000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2202
_reflns_number_total             2730
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2730
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0359P)²+0.7493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0877
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C2(H2A), C8(H8), C11(H11), C12(H12), C1(H1)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.2500 0.2500 0.33593(8) 0.02046(15) Uani 1 4 d S T P . .
Cl2 Cl 0.2500 0.7500 1.0000 0.0254(3) Uani 1 4 d S T P . .
Cl1 Cl 0.2500 0.2500 -0.04406(16) 0.0278(3) Uani 1 4 d S T P . .
O1 O 0.39660(7) 0.52637(7) 1.0438(2) 0.0237(3) Uani 1 1 d . . . . .
N2 N 0.34901(9) 0.43010(9) 0.2880(3) 0.0235(4) Uani 1 1 d . . . . .
N4 N 0.36156(9) 0.63373(9) 1.1033(3) 0.0225(4) Uani 1 1 d . . . . .
N3 N 0.31428(9) 0.57137(9) 0.8618(3) 0.0235(4) Uani 1 1 d . . . . .
N1 N 0.29484(8) 0.33877(8) 0.3648(3) 0.0220(4) Uani 1 1 d . . . . .
C9 C 0.40204(11) 0.69849(10) 1.5870(3) 0.0252(5) Uani 1 1 d . . . . .
H9 H 0.3821 0.7272 1.6796 0.030 Uiso 1 1 calc R . . . .
C2 C 0.29838(10) 0.37987(10) 0.5244(3) 0.0245(5) Uani 1 1 d . . . . .
H2A H 0.2802 0.3698 0.6474 0.029 Uiso 1 1 calc R . . . .
C3 C 0.33190(10) 0.43716(10) 0.4785(3) 0.0224(5) Uani 1 1 d . . . . .
C6 C 0.35991(10) 0.57437(10) 1.0046(3) 0.0202(5) Uani 1 1 d . . . . .
C8 C 0.36892(10) 0.68577(10) 1.4163(3) 0.0218(5) Uani 1 1 d . . . . .
H8 H 0.3263 0.7054 1.3939 0.026 Uiso 1 1 calc R . . . .
C10 C 0.46414(10) 0.66996(11) 1.6256(3) 0.0244(5) Uani 1 1 d . . . . .
C11 C 0.49199(11) 0.62903(11) 1.4843(3) 0.0243(5) Uani 1 1 d . . . . .
H11 H 0.5344 0.6091 1.5074 0.029 Uiso 1 1 calc R . . . .
C12 C 0.46015(10) 0.61643(10) 1.3123(3) 0.0234(5) Uani 1 1 d . . . . .
H12 H 0.4808 0.5888 1.2184 0.028 Uiso 1 1 calc R . . . .
C7 C 0.39720(10) 0.64449(10) 1.2766(3) 0.0208(5) Uani 1 1 d . . . . .
C4 C 0.34928(11) 0.49889(11) 0.5906(3) 0.0283(5) Uani 1 1 d . . . . .
H4A H 0.3475 0.5383 0.5043 0.034 Uiso 1 1 calc R . . . .
H4B H 0.3956 0.4949 0.6402 0.034 Uiso 1 1 calc R . . . .
C13 C 0.50071(12) 0.68306(12) 1.8123(3) 0.0322(6) Uani 1 1 d . . . . .
H13A H 0.5432 0.7056 1.7851 0.048 Uiso 1 1 calc GR . . . .
H13B H 0.5095 0.6405 1.8776 0.048 Uiso 1 1 calc GR . . . .
H13C H 0.4731 0.7116 1.8951 0.048 Uiso 1 1 calc GR . . . .
C1 C 0.32574(10) 0.37102(10) 0.2251(3) 0.0234(5) Uani 1 1 d . . . . .
H1 H 0.3308 0.3547 0.0976 0.028 Uiso 1 1 calc R . . . .
C5 C 0.30180(10) 0.50948(10) 0.7572(3) 0.0236(5) Uani 1 1 d . . . . .
H5A H 0.2553 0.5100 0.7077 0.028 Uiso 1 1 calc R . . . .
H5B H 0.3059 0.4713 0.8472 0.028 Uiso 1 1 calc R . . . .
H4 H 0.3308(11) 0.6621(11) 1.076(3) 0.021(6) Uiso 1 1 d . . . . .
H3 H 0.2904(11) 0.6052(11) 0.835(3) 0.022(6) Uiso 1 1 d . . . . .
H2 H 0.3684(12) 0.4612(12) 0.218(4) 0.034(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 Cl1 2.6413(12) . ?
Cu1 N1 1.9972(17) . ?
Cu1 N1 1.9972(17) 3 ?
Cu1 N1 1.9972(17) 2 ?
Cu1 N1 1.9972(17) 4 ?
O1 C6 1.238(2) . ?
N2 C3 1.375(3) . ?
N2 C1 1.342(3) . ?
N4 C6 1.370(3) . ?
N4 C7 1.416(3) . ?
N3 C6 1.349(3) . ?
N3 C5 1.456(3) . ?
N1 C2 1.382(3) . ?
N1 C1 1.319(3) . ?
C9 C8 1.382(3) . ?
C9 C10 1.392(3) . ?
C2 C3 1.364(3) . ?
C3 C4 1.500(3) . ?
C8 C7 1.394(3) . ?
C10 C11 1.394(3) . ?
C10 C13 1.512(3) . ?
C11 C12 1.377(3) . ?
C12 C7 1.399(3) . ?
C4 C5 1.512(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 Cl1 95.77(5) 3 . ?
N1 Cu1 Cl1 95.77(5) . . ?
N1 Cu1 Cl1 95.77(5) 4 . ?
N1 Cu1 Cl1 95.77(5) 2 . ?
N1 Cu1 N1 168.46(11) 3 . ?
N1 Cu1 N1 89.422(11) 2 . ?
N1 Cu1 N1 168.46(11) 4 2 ?
N1 Cu1 N1 89.421(11) 3 2 ?
N1 Cu1 N1 89.421(11) 3 4 ?
N1 Cu1 N1 89.421(11) 4 . ?
C1 N2 C3 108.54(18) . . ?
C6 N4 C7 124.71(18) . . ?
C6 N3 C5 121.40(18) . . ?
C2 N1 Cu1 129.15(14) . . ?
C1 N1 Cu1 124.74(15) . . ?
C1 N1 C2 106.07(18) . . ?
C8 C9 C10 121.1(2) . . ?
C3 C2 N1 109.62(19) . . ?
N2 C3 C4 121.82(19) . . ?
C2 C3 N2 105.16(19) . . ?
C2 C3 C4 133.0(2) . . ?
O1 C6 N4 123.11(19) . . ?
O1 C6 N3 121.87(19) . . ?
N3 C6 N4 115.02(18) . . ?
C9 C8 C7 120.9(2) . . ?
C9 C10 C11 117.4(2) . . ?
C9 C10 C13 121.7(2) . . ?
C11 C10 C13 120.9(2) . . ?
C12 C11 C10 122.3(2) . . ?
C11 C12 C7 119.8(2) . . ?
C8 C7 N4 118.61(19) . . ?
C8 C7 C12 118.52(19) . . ?
C12 C7 N4 122.85(19) . . ?
C3 C4 C5 111.57(18) . . ?
N1 C1 N2 110.6(2) . . ?
N3 C5 C4 113.21(17) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1 -3 10 0.1131 -1.0080 -2.9913 10.0025 0.3471 0.9646 -0.0554
1 3 -10 0.0919 1.0080 2.9913 -10.0025 -0.3471 -0.9646 0.0554
-4 -28 -1 0.0640 -3.9908 -27.9901 -0.9994 0.0153 0.0589 1.0070
4 28 1 0.0508 3.9908 27.9901 0.9994 -0.0153 -0.0589 -1.0070
28 -1 -1 0.0378 28.0144 -1.0030 -1.0035 0.8831 -0.4633 -0.0810
-28 -1 0 0.0515 -28.0128 -0.9970 0.0033 -0.9062 0.3764 0.1668

_database_code_depnum_ccdc_archive 'CCDC 1016072'
#######################################################################
#
#                 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_sj4f
_audit_creation_date             2014-07-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C78 H96 Cu N24 O6, 2(N O3), 2(C H4 O)'
_chemical_formula_sum            'C80 H104 Cu N26 O14'
_chemical_formula_weight         1717.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         C39H48N13O6Cu
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.1000(7)
_cell_length_b                   13.3909(7)
_cell_length_c                   13.4410(6)
_cell_angle_alpha                75.123(4)
_cell_angle_beta                 77.751(4)
_cell_angle_gamma                74.712(4)
_cell_volume                     2171.59(19)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    8330
_cell_measurement_temperature    120
_cell_measurement_theta_max      32.3799
_cell_measurement_theta_min      1.5836
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear bluish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             907
_exptl_crystal_size_max          0.3434
_exptl_crystal_size_mid          0.1879
_exptl_crystal_size_min          0.1443
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29444
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         1.587
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 16.1511
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0435482000
_diffrn_orient_matrix_UB_12      0.0425846000
_diffrn_orient_matrix_UB_13      0.0097994000
_diffrn_orient_matrix_UB_21      0.0334869000
_diffrn_orient_matrix_UB_22      0.0213317000
_diffrn_orient_matrix_UB_23      0.0201076000
_diffrn_orient_matrix_UB_31      0.0145072000
_diffrn_orient_matrix_UB_32      0.0298359000
_diffrn_orient_matrix_UB_33      -0.0505406000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6765
_reflns_number_total             8537
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.378
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     608
_refine_ls_number_reflns         8537
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0750P)²+1.3369P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1563
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: O4(0.6) H4C(0.6) O8(0.4) H8B(0.4) C1A(0.6) H1AA(0.6) H1AB(0.6)
 H1AC(0.6) C1B(0.4) H1BA(0.4) H1BB(0.4) H1BC(0.4)
3.a Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C31(H31A,H31B), C4(H4A,H4B), C17(H17A,H17B), C18(H18A,H18B),
 C5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C11(H11A), C14(H14), C8(H8A), C35(H35), C27(H27), C15(H15), C34(H34),
 C38(H38), C12(H12A), C37(H37), C24(H24), C2(H2A), C25(H25), C22(H22), C9(H9),
 C28(H28), C21(H21)
3.c Idealised Me refined as rotating group:
 C13(H13B,H13C,H13A), C26(H26A,H26B,H26C), C39(H39A,H39B,H39C), C1A(H1AA,H1AB,
 H1AC), C1B(H1BA,H1BB,H1BC)
3.d Idealised tetrahedral OH refined as rotating group:
 O4(H4C), O8(H8B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.5000 0.0000 0.01839(14) Uani 1 2 d S T P . .
O1 O -0.49254(16) 0.21313(17) 0.08093(16) 0.0363(5) Uani 1 1 d . . . . .
O5 O 0.38410(18) 0.04236(18) 0.42920(16) 0.0389(5) Uani 1 1 d . . . . .
O3 O 0.29615(17) 0.42268(19) 0.49027(16) 0.0388(5) Uani 1 1 d . . . . .
O2 O 0.07853(16) -0.00172(16) -0.28934(15) 0.0296(5) Uani 1 1 d . . . . .
O7 O 0.41893(17) -0.11610(18) 0.52248(17) 0.0401(5) Uani 1 1 d . . . . .
N10 N 0.2941(2) 0.3308(2) 0.0905(2) 0.0304(6) Uani 1 1 d . . . . .
N12 N 0.4508(2) 0.3163(2) 0.5450(2) 0.0359(7) Uani 1 1 d . . . . .
N2 N -0.08605(19) 0.2160(2) 0.17055(18) 0.0257(5) Uani 1 1 d . . . . .
N4 N -0.5336(2) 0.0585(2) 0.1813(2) 0.0314(6) Uani 1 1 d . . . . .
O6 O 0.52582(16) -0.07153(17) 0.38014(16) 0.0344(5) Uani 1 1 d . . . . .
N7 N 0.2229(2) 0.0689(2) -0.3695(2) 0.0283(6) Uani 1 1 d . . . . .
N9 N 0.13469(18) 0.42900(18) 0.06762(17) 0.0225(5) Uani 1 1 d . . . . .
N6 N 0.1789(2) 0.4013(2) -0.2999(2) 0.0314(6) Uani 1 1 d . . . . .
N13 N 0.44268(16) -0.04767(17) 0.44435(16) 0.0170(4) Uani 1 1 d . . . . .
N3 N -0.4059(2) 0.1248(2) 0.2183(2) 0.0332(6) Uani 1 1 d . . . . .
N11 N 0.3831(2) 0.2821(2) 0.41728(19) 0.0316(6) Uani 1 1 d . . . . .
N1 N -0.06425(17) 0.36839(18) 0.06973(16) 0.0221(5) Uani 1 1 d . . . . .
N5 N 0.08010(19) 0.42270(19) -0.14883(18) 0.0269(5) Uani 1 1 d . . . . .
N8 N 0.1822(2) -0.0543(2) -0.4352(2) 0.0300(6) Uani 1 1 d . . . . .
C1 C -0.0293(2) 0.2911(2) 0.1461(2) 0.0231(6) Uani 1 1 d . . . . .
H1 H 0.0286 0.2889 0.1795 0.028 Uiso 1 1 calc R . . . .
C11 C -0.8040(3) 0.0346(3) 0.1664(3) 0.0460(9) Uani 1 1 d . . . . .
H11A H -0.8649 0.0167 0.2133 0.055 Uiso 1 1 calc R . . . .
C6 C -0.4783(2) 0.1371(2) 0.1552(2) 0.0280(6) Uani 1 1 d . . . . .
C10 C -0.8062(2) 0.0592(3) 0.0604(3) 0.0371(8) Uani 1 1 d . . . . .
C14 C 0.1524(2) 0.4580(2) -0.2254(2) 0.0281(6) Uani 1 1 d . . . . .
H14 H 0.1819 0.5163 -0.2274 0.034 Uiso 1 1 calc R . . . .
C8 C -0.6251(2) 0.0854(2) 0.0322(2) 0.0290(6) Uani 1 1 d . . . . .
H8A H -0.5640 0.1030 -0.0148 0.035 Uiso 1 1 calc R . . . .
C7 C -0.6241(2) 0.0607(2) 0.1385(2) 0.0282(6) Uani 1 1 d . . . . .
C30 C 0.3337(3) 0.3766(3) 0.2456(3) 0.0415(8) Uani 1 1 d . . . . .
H30A H 0.3256 0.4467 0.2616 0.050 Uiso 1 1 calc R . . . .
H30B H 0.4093 0.3530 0.2147 0.050 Uiso 1 1 calc R . . . .
C20 C 0.1357(2) -0.1391(2) -0.4342(2) 0.0265(6) Uani 1 1 d . . . . .
C36 C 0.4517(3) 0.4366(3) 0.8066(2) 0.0359(7) Uani 1 1 d . . . . .
C35 C 0.4770(3) 0.3291(3) 0.8098(3) 0.0449(9) Uani 1 1 d . . . . .
H35 H 0.4954 0.2809 0.8721 0.054 Uiso 1 1 calc R . . . .
C27 C 0.2156(2) 0.3575(2) 0.0322(2) 0.0247(6) Uani 1 1 d . . . . .
H27 H 0.2178 0.3289 -0.0262 0.030 Uiso 1 1 calc R . . . .
C15 C 0.0604(3) 0.3387(2) -0.1779(2) 0.0310(7) Uani 1 1 d . . . . .
H15 H 0.0119 0.2963 -0.1379 0.037 Uiso 1 1 calc R . . . .
C13 C -0.9035(3) 0.0573(3) 0.0185(3) 0.0490(10) Uani 1 1 d . . . . .
H13B H -0.9365 0.0001 0.0629 0.074 Uiso 1 1 calc GR . . . .
H13C H -0.8820 0.0452 -0.0526 0.074 Uiso 1 1 calc GR . . . .
H13A H -0.9551 0.1253 0.0179 0.074 Uiso 1 1 calc GR . . . .
C34 C 0.4762(3) 0.2899(3) 0.7239(3) 0.0424(8) Uani 1 1 d . . . . .
H34 H 0.4944 0.2156 0.7280 0.051 Uiso 1 1 calc R . . . .
C33 C 0.4489(2) 0.3588(3) 0.6321(2) 0.0307(7) Uani 1 1 d . . . . .
C3 C -0.1629(2) 0.2453(2) 0.1068(2) 0.0255(6) Uani 1 1 d . . . . .
C38 C 0.4242(2) 0.4673(2) 0.6275(2) 0.0295(6) Uani 1 1 d . . . . .
H38 H 0.4067 0.5158 0.5650 0.035 Uiso 1 1 calc R . . . .
C23 C 0.0507(2) -0.3094(2) -0.4378(2) 0.0303(7) Uani 1 1 d . . . . .
C12 C -0.7143(3) 0.0356(3) 0.2058(2) 0.0395(8) Uani 1 1 d . . . . .
H12A H -0.7148 0.0190 0.2790 0.047 Uiso 1 1 calc R . . . .
C29 C 0.2631(2) 0.3879(2) 0.1675(2) 0.0308(7) Uani 1 1 d . . . . .
C32 C 0.3718(2) 0.3454(2) 0.4841(2) 0.0284(6) Uani 1 1 d . . . . .
C16 C 0.1201(2) 0.3248(2) -0.2719(2) 0.0318(7) Uani 1 1 d . . . . .
C37 C 0.4253(2) 0.5044(3) 0.7138(2) 0.0317(7) Uani 1 1 d . . . . .
H37 H 0.4073 0.5786 0.7098 0.038 Uiso 1 1 calc R . . . .
C24 C 0.1608(2) -0.3171(3) -0.4561(2) 0.0344(7) Uani 1 1 d . . . . .
H24 H 0.2077 -0.3809 -0.4703 0.041 Uiso 1 1 calc R . . . .
C2 C -0.1489(2) 0.3397(2) 0.0455(2) 0.0269(6) Uani 1 1 d . . . . .
H2A H -0.1910 0.3805 -0.0067 0.032 Uiso 1 1 calc R . . . .
C31 C 0.3089(2) 0.2991(2) 0.3453(2) 0.0278(6) Uani 1 1 d . . . . .
H31A H 0.2353 0.3257 0.3794 0.033 Uiso 1 1 calc R . . . .
H31B H 0.3110 0.2305 0.3289 0.033 Uiso 1 1 calc R . . . .
C25 C 0.2033(2) -0.2335(2) -0.4539(2) 0.0331(7) Uani 1 1 d . . . . .
H25 H 0.2787 -0.2406 -0.4659 0.040 Uiso 1 1 calc R . . . .
C19 C 0.1555(2) 0.0048(2) -0.3604(2) 0.0242(6) Uani 1 1 d . . . . .
C4 C -0.2417(2) 0.1791(2) 0.1144(2) 0.0311(7) Uani 1 1 d . . . . .
H4A H -0.2051 0.1032 0.1285 0.037 Uiso 1 1 calc R . . . .
H4B H -0.2681 0.1957 0.0469 0.037 Uiso 1 1 calc R . . . .
C17 C 0.1304(3) 0.2463(3) -0.3371(3) 0.0406(8) Uani 1 1 d . . . . .
H17A H 0.1566 0.2768 -0.4105 0.049 Uiso 1 1 calc R . . . .
H17B H 0.0589 0.2330 -0.3343 0.049 Uiso 1 1 calc R . . . .
C22 C -0.0150(2) -0.2145(2) -0.4190(2) 0.0289(6) Uani 1 1 d . . . . .
H22 H -0.0904 -0.2074 -0.4068 0.035 Uiso 1 1 calc R . . . .
C9 C -0.7154(2) 0.0844(3) -0.0057(2) 0.0337(7) Uani 1 1 d . . . . .
H9 H -0.7151 0.1013 -0.0788 0.040 Uiso 1 1 calc R . . . .
C28 C 0.1634(2) 0.4476(2) 0.1529(2) 0.0268(6) Uani 1 1 d . . . . .
H28 H 0.1202 0.4949 0.1952 0.032 Uiso 1 1 calc R . . . .
C26 C 0.0064(3) -0.4023(3) -0.4391(3) 0.0388(8) Uani 1 1 d . . . . .
H26A H 0.0530 -0.4413 -0.4904 0.058 Uiso 1 1 calc GR . . . .
H26B H -0.0658 -0.3764 -0.4578 0.058 Uiso 1 1 calc GR . . . .
H26C H 0.0032 -0.4493 -0.3698 0.058 Uiso 1 1 calc GR . . . .
C21 C 0.0254(2) -0.1296(2) -0.4172(2) 0.0270(6) Uani 1 1 d . . . . .
H21 H -0.0218 -0.0653 -0.4044 0.032 Uiso 1 1 calc R . . . .
C39 C 0.4513(3) 0.4783(3) 0.9010(2) 0.0470(9) Uani 1 1 d . . . . .
H39A H 0.3777 0.5114 0.9273 0.070 Uiso 1 1 calc GR . . . .
H39B H 0.4957 0.5309 0.8816 0.070 Uiso 1 1 calc GR . . . .
H39C H 0.4801 0.4196 0.9554 0.070 Uiso 1 1 calc GR . . . .
C18 C 0.2063(2) 0.1422(2) -0.3014(2) 0.0268(6) Uani 1 1 d . . . . .
H18A H 0.2762 0.1561 -0.2988 0.032 Uiso 1 1 calc R . . . .
H18B H 0.1771 0.1090 -0.2300 0.032 Uiso 1 1 calc R . . . .
C5 C -0.3371(2) 0.1985(2) 0.2007(2) 0.0302(7) Uani 1 1 d . . . . .
H5A H -0.3103 0.1917 0.2662 0.036 Uiso 1 1 calc R . . . .
H5B H -0.3795 0.2717 0.1816 0.036 Uiso 1 1 calc R . . . .
H11 H 0.432(3) 0.232(3) 0.418(2) 0.028(9) Uiso 1 1 d . . . . .
H12 H 0.482(3) 0.259(3) 0.546(3) 0.047(12) Uiso 1 1 d . . . . .
H3 H -0.405(3) 0.075(3) 0.272(2) 0.031(9) Uiso 1 1 d . . . . .
H10 H 0.354(3) 0.287(3) 0.079(2) 0.029(9) Uiso 1 1 d . . . . .
H2 H -0.078(2) 0.160(2) 0.216(2) 0.019(7) Uiso 1 1 d . . . . .
H4 H -0.535(3) 0.022(3) 0.240(3) 0.036(10) Uiso 1 1 d . . . . .
H8 H 0.236(3) -0.055(3) -0.462(2) 0.024(9) Uiso 1 1 d . . . . .
H7 H 0.272(3) 0.074(3) -0.421(2) 0.032(9) Uiso 1 1 d . . . . .
H6 H 0.218(3) 0.417(3) -0.358(3) 0.045(11) Uiso 1 1 d . . . . .
O4 O -0.1785(4) 0.4260(4) -0.3283(3) 0.0559(11) Uani 0.6 1 d . . . A 1
H4C H -0.2184 0.4652 -0.3709 0.084 Uiso 0.6 1 calc GR . . A 1
O8 O -0.0653(5) 0.1628(5) -0.1898(5) 0.0463(15) Uani 0.4 1 d . . . B 2
H8B H -0.0755 0.1666 -0.1269 0.069 Uiso 0.4 1 calc GR . . B 2
C1A C -0.2207(7) 0.3354(7) -0.2757(6) 0.073(2) Uani 0.6 1 d . . . A 1
H1AA H -0.2028 0.3119 -0.2049 0.109 Uiso 0.6 1 calc GR . . A 1
H1AB H -0.1898 0.2783 -0.3137 0.109 Uiso 0.6 1 calc GR . . A 1
H1AC H -0.2988 0.3537 -0.2722 0.109 Uiso 0.6 1 calc GR . . A 1
C1B C -0.1532(9) 0.2240(10) -0.2356(10) 0.075(3) Uani 0.4 1 d . . . B 2
H1BA H -0.2163 0.1948 -0.2025 0.112 Uiso 0.4 1 calc GR . . B 2
H1BB H -0.1391 0.2237 -0.3101 0.112 Uiso 0.4 1 calc GR . . B 2
H1BC H -0.1662 0.2969 -0.2265 0.112 Uiso 0.4 1 calc GR . . B 2


_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 N9 2.048(2) . ?
Cu1 N9 2.048(2) 2_565 ?
Cu1 N1 2.072(2) 2_565 ?
Cu1 N1 2.072(2) . ?
Cu1 N5 2.403(2) 2_565 ?
Cu1 N5 2.403(2) . ?
O1 C6 1.235(3) . ?
O5 N13 1.239(3) . ?
O3 C32 1.236(4) . ?
O2 C19 1.237(3) . ?
O7 N13 1.248(3) . ?
N10 C27 1.344(3) . ?
N10 C29 1.373(4) . ?
N12 C33 1.420(4) . ?
N12 C32 1.370(4) . ?
N2 C1 1.339(4) . ?
N2 C3 1.373(4) . ?
N4 C6 1.365(4) . ?
N4 C7 1.414(4) . ?
O6 N13 1.262(3) . ?
N7 C19 1.354(4) . ?
N7 C18 1.454(4) . ?
N9 C27 1.323(4) . ?
N9 C28 1.377(3) . ?
N6 C14 1.344(4) . ?
N6 C16 1.370(4) . ?
N3 C6 1.353(4) . ?
N3 C5 1.449(4) . ?
N11 C32 1.348(4) . ?
N11 C31 1.450(4) . ?
N1 C1 1.319(3) . ?
N1 C2 1.388(3) . ?
N5 C14 1.324(4) . ?
N5 C15 1.380(4) . ?
N8 C20 1.419(4) . ?
N8 C19 1.369(4) . ?
C11 C10 1.382(5) . ?
C11 C12 1.392(4) . ?
C10 C13 1.507(4) . ?
C10 C9 1.388(4) . ?
C8 C7 1.383(4) . ?
C8 C9 1.388(4) . ?
C7 C12 1.388(4) . ?
C30 C29 1.496(4) . ?
C30 C31 1.502(4) . ?
C20 C25 1.391(4) . ?
C20 C21 1.391(4) . ?
C36 C35 1.381(5) . ?
C36 C37 1.392(4) . ?
C36 C39 1.510(4) . ?
C35 C34 1.388(5) . ?
C15 C16 1.367(4) . ?
C34 C33 1.390(4) . ?
C33 C38 1.391(4) . ?
C3 C2 1.354(4) . ?
C3 C4 1.502(4) . ?
C38 C37 1.377(4) . ?
C23 C24 1.392(4) . ?
C23 C22 1.384(4) . ?
C23 C26 1.509(4) . ?
C29 C28 1.364(4) . ?
C16 C17 1.497(4) . ?
C24 C25 1.384(4) . ?
C4 C5 1.531(4) . ?
C17 C18 1.514(4) . ?
C22 C21 1.381(4) . ?
O4 C1A 1.423(8) . ?
O8 C1B 1.386(12) . ?

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
N9 Cu1 N9 180.0 . 2_565 ?
N9 Cu1 N1 90.25(9) . . ?
N9 Cu1 N1 89.76(9) . 2_565 ?
N9 Cu1 N1 89.76(9) 2_565 . ?
N9 Cu1 N1 90.24(9) 2_565 2_565 ?
N9 Cu1 N5 89.69(8) . 2_565 ?
N9 Cu1 N5 89.69(8) 2_565 . ?
N9 Cu1 N5 90.31(8) 2_565 2_565 ?
N9 Cu1 N5 90.31(8) . . ?
N1 Cu1 N1 180.0 2_565 . ?
N1 Cu1 N5 89.65(8) . . ?
N1 Cu1 N5 90.35(8) . 2_565 ?
N1 Cu1 N5 89.66(8) 2_565 2_565 ?
N1 Cu1 N5 90.34(8) 2_565 . ?
N5 Cu1 N5 180.0 2_565 . ?
C27 N10 C29 108.4(3) . . ?
C32 N12 C33 125.3(3) . . ?
C1 N2 C3 108.5(2) . . ?
C6 N4 C7 125.1(3) . . ?
C19 N7 C18 122.8(2) . . ?
C27 N9 Cu1 125.03(18) . . ?
C27 N9 C28 106.1(2) . . ?
C28 N9 Cu1 128.8(2) . . ?
C14 N6 C16 108.2(3) . . ?
O5 N13 O7 120.2(2) . . ?
O5 N13 O6 120.4(2) . . ?
O7 N13 O6 119.4(2) . . ?
C6 N3 C5 122.0(3) . . ?
C32 N11 C31 123.2(3) . . ?
C1 N1 Cu1 126.15(18) . . ?
C1 N1 C2 105.1(2) . . ?
C2 N1 Cu1 128.71(18) . . ?
C14 N5 Cu1 125.23(19) . . ?
C14 N5 C15 104.6(2) . . ?
C15 N5 Cu1 130.1(2) . . ?
C19 N8 C20 125.0(3) . . ?
N1 C1 N2 111.1(2) . . ?
C10 C11 C12 121.4(3) . . ?
O1 C6 N4 123.4(3) . . ?
O1 C6 N3 122.6(3) . . ?
N3 C6 N4 114.0(3) . . ?
C11 C10 C13 121.0(3) . . ?
C11 C10 C9 117.7(3) . . ?
C9 C10 C13 121.4(3) . . ?
N5 C14 N6 111.6(3) . . ?
C7 C8 C9 119.9(3) . . ?
C8 C7 N4 122.3(3) . . ?
C8 C7 C12 119.2(3) . . ?
C12 C7 N4 118.6(3) . . ?
C29 C30 C31 113.1(3) . . ?
C25 C20 N8 118.4(3) . . ?
C21 C20 N8 122.2(3) . . ?
C21 C20 C25 119.4(3) . . ?
C35 C36 C37 117.3(3) . . ?
C35 C36 C39 121.0(3) . . ?
C37 C36 C39 121.6(3) . . ?
C36 C35 C34 121.5(3) . . ?
N9 C27 N10 110.5(3) . . ?
C16 C15 N5 110.8(3) . . ?
C35 C34 C33 120.3(3) . . ?
C34 C33 N12 119.0(3) . . ?
C34 C33 C38 118.8(3) . . ?
C38 C33 N12 122.1(3) . . ?
N2 C3 C4 122.3(3) . . ?
C2 C3 N2 105.1(2) . . ?
C2 C3 C4 132.6(3) . . ?
C37 C38 C33 119.8(3) . . ?
C24 C23 C26 120.3(3) . . ?
C22 C23 C24 117.5(3) . . ?
C22 C23 C26 122.2(3) . . ?
C7 C12 C11 120.2(3) . . ?
N10 C29 C30 121.5(3) . . ?
C28 C29 N10 105.4(2) . . ?
C28 C29 C30 133.1(3) . . ?
O3 C32 N12 123.0(3) . . ?
O3 C32 N11 122.7(3) . . ?
N11 C32 N12 114.3(3) . . ?
N6 C16 C17 122.5(3) . . ?
C15 C16 N6 104.8(3) . . ?
C15 C16 C17 132.7(3) . . ?
C38 C37 C36 122.2(3) . . ?
C25 C24 C23 121.3(3) . . ?
C3 C2 N1 110.3(2) . . ?
N11 C31 C30 112.8(2) . . ?
C24 C25 C20 120.1(3) . . ?
O2 C19 N7 123.0(3) . . ?
O2 C19 N8 123.2(3) . . ?
N7 C19 N8 113.7(2) . . ?
C3 C4 C5 112.0(2) . . ?
C16 C17 C18 112.5(2) . . ?
C21 C22 C23 122.3(3) . . ?
C10 C9 C8 121.8(3) . . ?
C29 C28 N9 109.7(3) . . ?
C22 C21 C20 119.4(3) . . ?
N7 C18 C17 112.5(2) . . ?
N3 C5 C4 112.4(3) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4 18 -1 0.0859 3.9999 18.0000 -1.0000 0.5825 0.4978 0.6456
-4 -18 1 0.0859 -3.9999 -18.0000 1.0000 -0.5825 -0.4978 -0.6456
3 2 -17 0.1130 3.0000 2.0000 -17.0000 -0.2121 -0.1987 0.9624
-2 6 18 0.1287 -2.0000 6.0000 18.0000 0.5190 0.4230 -0.7597
-18 -2 -1 0.0462 -17.9999 -1.9999 -1.0000 0.6889 -0.6655 -0.2703
18 2 1 0.0982 17.9999 1.9999 1.0000 -0.6889 0.6655 0.2703

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_database_code_depnum_ccdc_archive 'CCDC 1016073'
