# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kell2
_database_code_depnum_ccdc_archive 'CCDC 1403896'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 Cu N4 O, 2(N O3)'
_chemical_formula_sum            'C24 H18 Cu N6 O7'
_chemical_formula_weight         565.98

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_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. 
The complex was found in the CSD (version 5.36, Feb 2015; Allen, 2002) 
a number of times. In the present case, the I2/a space group was chosen 
over C2/c to reduce the value of the b angle but the reduced call is 
the same as the earlier reports, except that by Szpakolski et al. (2010) 
which appears to be a genuinely different polymorph. However, in each 
case the basic structure and packing are very similar.

;

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

_cell_length_a                   16.6086(15)
_cell_length_b                   7.1589(6)
_cell_length_c                   19.141(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.1790(10)
_cell_angle_gamma                90
_cell_volume                     2224.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6719
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      29.43

_exptl_crystal_description       lozenge
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_F_000             1156
_exptl_transmission_factor_min   0.6556
_exptl_transmission_factor_max   0.7459
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.045
_shelx_estimated_absorpt_T_min   0.758
_shelx_estimated_absorpt_T_max   0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6556
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   'SADABS v2012/1, Sheldrick, G.M., (2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX 2 CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12031
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.177
_diffrn_reflns_theta_max         29.509
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3092
_reflns_number_gt                2884
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury'
_computing_publication_material  'Bruker SHELXTL, PublCIF'
_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)+(0.0413P)²+2.0021P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3092
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0786
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.7500 0.60178(3) 0.5000 0.02030(8) Uani 1 2 d S T P . .
O1 O 0.7500 0.3012(3) 0.5000 0.0457(5) Uani 1 2 d S T P . .
H1A H 0.7446(18) 0.238(4) 0.4653(13) 0.069 Uiso 1 1 d . U . . .
N1 N 0.64316(7) 0.69821(16) 0.52232(6) 0.0200(2) Uani 1 1 d . . . . .
N2 N 0.68110(7) 0.58253(16) 0.40086(6) 0.0201(2) Uani 1 1 d . . . . .
C1 C 0.62633(9) 0.7642(2) 0.58286(7) 0.0236(3) Uani 1 1 d . . . . .
H1 H 0.6701 0.7807 0.6232 0.028 Uiso 1 1 calc R U . . .
C2 C 0.54584(9) 0.8100(2) 0.58866(8) 0.0271(3) Uani 1 1 d . . . . .
H2 H 0.5358 0.8553 0.6327 0.033 Uiso 1 1 calc R U . . .
C3 C 0.48173(9) 0.7895(2) 0.53122(8) 0.0262(3) Uani 1 1 d . . . . .
H3 H 0.4271 0.8187 0.5352 0.031 Uiso 1 1 calc R U . . .
C4 C 0.49782(8) 0.72449(19) 0.46593(8) 0.0220(3) Uani 1 1 d . . . . .
C5 C 0.43526(8) 0.6982(2) 0.40247(9) 0.0266(3) Uani 1 1 d . . . . .
H5 H 0.3798 0.7294 0.4029 0.032 Uiso 1 1 calc R U . . .
C6 C 0.45418(9) 0.6295(2) 0.34193(8) 0.0261(3) Uani 1 1 d . . . . .
H6 H 0.4115 0.6098 0.3010 0.031 Uiso 1 1 calc R U . . .
C7 C 0.53772(8) 0.58617(18) 0.33867(7) 0.0214(3) Uani 1 1 d . . . . .
C8 C 0.56131(9) 0.5153(2) 0.27728(7) 0.0256(3) Uani 1 1 d . . . . .
H8 H 0.5209 0.4895 0.2353 0.031 Uiso 1 1 calc R U . . .
C9 C 0.64301(9) 0.4839(2) 0.27865(8) 0.0264(3) Uani 1 1 d . . . . .
H9 H 0.6598 0.4387 0.2373 0.032 Uiso 1 1 calc R U . . .
C10 C 0.70167(9) 0.5191(2) 0.34149(7) 0.0240(3) Uani 1 1 d . . . . .
H10 H 0.7581 0.4970 0.3418 0.029 Uiso 1 1 calc R U . . .
C11 C 0.60022(8) 0.61580(17) 0.39950(7) 0.0186(2) Uani 1 1 d . . . . .
C12 C 0.57981(8) 0.68133(18) 0.46438(7) 0.0189(2) Uani 1 1 d . . . . .
N3 N 0.68465(7) 0.03411(17) 0.34185(7) 0.0246(2) Uani 1 1 d . . . . .
O2 O 0.74951(8) 0.0990(2) 0.37991(9) 0.0494(4) Uani 1 1 d . . . . .
O3 O 0.61735(8) 0.0568(2) 0.35893(8) 0.0415(3) Uani 1 1 d . . . . .
O4 O 0.68915(9) -0.0521(2) 0.28652(7) 0.0435(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 2.0033(12) 2_656 ?
Cu1 N2 2.0033(12) . ?
Cu1 N1 2.0317(11) . ?
Cu1 N1 2.0317(11) 2_656 ?
Cu1 O1 2.1520(18) . ?
N1 C1 1.3344(17) . ?
N1 C12 1.3636(17) . ?
N2 C10 1.3334(17) . ?
N2 C11 1.3591(17) . ?
C1 C2 1.403(2) . ?
C2 C3 1.367(2) . ?
C3 C4 1.411(2) . ?
C4 C12 1.4027(18) . ?
C4 C5 1.435(2) . ?
C5 C6 1.355(2) . ?
C6 C7 1.436(2) . ?
C7 C11 1.4030(18) . ?
C7 C8 1.409(2) . ?
C8 C9 1.370(2) . ?
C9 C10 1.4018(19) . ?
C11 C12 1.4334(18) . ?
N3 O3 1.2395(17) . ?
N3 O4 1.2416(18) . ?
N3 O2 1.2552(17) . ?

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
N2 Cu1 N2 172.11(7) 2_656 . ?
N2 Cu1 N1 100.01(5) 2_656 . ?
N2 Cu1 N1 82.70(5) . . ?
N2 Cu1 N1 82.70(5) 2_656 2_656 ?
N2 Cu1 N1 100.01(5) . 2_656 ?
N1 Cu1 N1 140.27(7) . 2_656 ?
N2 Cu1 O1 86.06(3) 2_656 . ?
N2 Cu1 O1 86.06(3) . . ?
N1 Cu1 O1 109.86(3) . . ?
N1 Cu1 O1 109.86(3) 2_656 . ?
C1 N1 C12 118.07(11) . . ?
C1 N1 Cu1 130.93(10) . . ?
C12 N1 Cu1 110.92(8) . . ?
C10 N2 C11 118.25(12) . . ?
C10 N2 Cu1 129.26(10) . . ?
C11 N2 Cu1 111.77(9) . . ?
N1 C1 C2 121.93(13) . . ?
C3 C2 C1 120.30(13) . . ?
C2 C3 C4 119.12(13) . . ?
C12 C4 C3 117.23(13) . . ?
C12 C4 C5 119.09(13) . . ?
C3 C4 C5 123.68(13) . . ?
C6 C5 C4 120.96(13) . . ?
C5 C6 C7 121.06(13) . . ?
C11 C7 C8 117.34(12) . . ?
C11 C7 C6 118.93(13) . . ?
C8 C7 C6 123.73(13) . . ?
C9 C8 C7 119.44(13) . . ?
C8 C9 C10 119.55(13) . . ?
N2 C10 C9 122.40(13) . . ?
N2 C11 C7 122.99(12) . . ?
N2 C11 C12 117.02(11) . . ?
C7 C11 C12 119.98(12) . . ?
N1 C12 C4 123.31(12) . . ?
N1 C12 C11 116.79(11) . . ?
C4 C12 C11 119.90(12) . . ?
O3 N3 O4 120.67(14) . . ?
O3 N3 O2 120.64(14) . . ?
O4 N3 O2 118.69(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O2 0.79(3) 1.93(3) 2.7150(18) 171(3) .

_refine_diff_density_max         0.481
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.064

_shelxl_version_number           2014/6



