# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_xb9535_sq
_database_code_depnum_ccdc_archive 'CCDC 1584011'
_audit_update_record             
;
2017-11-05 deposited with the CCDC.
2018-12-07 downloaded from the CCDC.
;
_audit_creation_date             2016-05-25
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H4 Cu3 N16 Na O4'
_chemical_formula_sum            'C8 H4 Cu3 N16 Na O4'
_chemical_formula_weight         601.88
_chemical_melting_point          ?
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'
Na Na 0.0362 0.0249 '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      tetragonal
_space_group_IT_number           141
_space_group_name_H-M_alt        'I 41/a m d'
_space_group_name_Hall           '-I 4bd 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/4, x+3/4, z+1/4'
'-x+1/2, -y, z+1/2'
'y+1/4, -x+1/4, z+3/4'
'x, -y, -z'
'y+1/4, x+3/4, -z+1/4'
'-x+1/2, y, -z+1/2'
'-y+1/4, -x+1/4, -z+3/4'
'x+1/2, y+1/2, z+1/2'
'-y+3/4, x+5/4, z+3/4'
'-x+1, -y+1/2, z+1'
'y+3/4, -x+3/4, z+5/4'
'x+1/2, -y+1/2, -z+1/2'
'y+3/4, x+5/4, -z+3/4'
'-x+1, y+1/2, -z+1'
'-y+3/4, -x+3/4, -z+5/4'
'-x, -y, -z'
'y-1/4, -x-3/4, -z-1/4'
'x-1/2, y, -z-1/2'
'-y-1/4, x-1/4, -z-3/4'
'-x, y, z'
'-y-1/4, -x-3/4, z-1/4'
'x-1/2, -y, z-1/2'
'y-1/4, x-1/4, z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/4, -x-1/4, -z+1/4'
'x, y+1/2, -z'
'-y+1/4, x+1/4, -z-1/4'
'-x+1/2, y+1/2, z+1/2'
'-y+1/4, -x-1/4, z+1/4'
'x, -y+1/2, z'
'y+1/4, x+1/4, z-1/4'

_cell_length_a                   13.638(3)
_cell_length_b                   13.638(3)
_cell_length_c                   11.428(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2125.6(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    586
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.36
_cell_measurement_theta_min      2.99
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.048
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0966 before and 0.0497 after correction.
The Ratio of minimum to maximum transmission is 0.8391.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.881
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_av_unetI/netI     0.0347
_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       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5475
_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         26.244
_diffrn_reflns_theta_min         2.325
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                429
_reflns_number_total             585
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.655
_refine_diff_density_rms         0.132
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     51
_refine_ls_number_reflns         585
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0534
_refine_ls_restrained_S_all      1.250
_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)+(0.0827P)²+19.7884P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1657
_refine_ls_wR_factor_ref         0.1803
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.009 and
sigma for terminal atoms of 0.009
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.5000 0.7500 0.3750 0.0349(7) Uani 1 8 d S T P . .
Cu2 Cu 0.5000 0.5000 0.5000 0.0413(6) Uani 1 4 d S T P . .
Na1 Na 0.5000 0.2500 0.1250 0.0383(18) Uani 1 8 d S T P . .
O1 O 0.5000 0.3717(6) 0.2599(6) 0.054(2) Uani 1 2 d S T P . .
N1 N 0.5000 0.5139(6) 0.1477(6) 0.0357(19) Uani 1 2 d S T P . .
N4 N 0.5000 0.4698(6) 0.0407(7) 0.043(2) Uani 1 2 d S T P . .
N2 N 0.5000 0.6230(6) 0.2878(7) 0.045(2) Uani 1 2 d S T P . .
N3 N 0.5000 0.5264(6) 0.3391(6) 0.038(2) Uani 1 2 d S T P . .
C1 C 0.5000 0.4599(8) 0.2527(8) 0.038(2) Uani 1 2 d S T P . .
C2 C 0.5000 0.6124(9) 0.1763(9) 0.050(3) Uani 1 2 d S T P . .
H2 H 0.5000 0.6636 0.1225 0.060 Uiso 1 2 calc RS T P . .


_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 1.998(9) . ?
Cu1 N2 1.998(9) 18_576 ?
Cu1 N2 1.998(9) 11_564 ?
Cu1 N2 1.998(9) 28_656 ?
Cu2 N3 1.874(7) 17_666 ?
Cu2 N3 1.874(7) . ?
Na1 O1 2.266(7) . ?
Na1 O1 2.266(7) 20_656 ?
Na1 O1 2.266(7) 26_565 ?
Na1 O1 2.266(7) 11_554 ?
O1 C1 1.205(13) . ?
N1 N4 1.362(11) . ?
N1 C1 1.409(12) . ?
N1 C2 1.383(14) . ?
N4 N4 1.242(17) 17_665 ?
N2 N3 1.442(11) . ?
N2 C2 1.283(12) . ?
N3 C1 1.341(12) . ?
C2 H2 0.9300 . ?

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 104.4(2) . 28_656 ?
N2 Cu1 N2 120.2(5) 28_656 18_576 ?
N2 Cu1 N2 104.4(2) . 18_576 ?
N2 Cu1 N2 104.4(2) 28_656 11_564 ?
N2 Cu1 N2 104.4(2) 18_576 11_564 ?
N2 Cu1 N2 120.2(5) . 11_564 ?
N3 Cu2 N3 180.0 17_666 . ?
O1 Na1 O1 117.58(19) 20_656 11_554 ?
O1 Na1 O1 117.58(19) . 20_656 ?
O1 Na1 O1 94.2(3) 20_656 26_565 ?
O1 Na1 O1 94.2(3) . 11_554 ?
O1 Na1 O1 117.58(19) . 26_565 ?
O1 Na1 O1 117.58(19) 26_565 11_554 ?
C1 O1 Na1 133.2(6) . . ?
N4 N1 C1 122.3(8) . . ?
N4 N1 C2 129.9(8) . . ?
C2 N1 C1 107.8(8) . . ?
N4 N4 N1 112.3(11) 17_665 . ?
N3 N2 Cu1 126.1(6) . . ?
C2 N2 Cu1 126.4(8) . . ?
C2 N2 N3 107.5(9) . . ?
N2 N3 Cu2 125.1(6) . . ?
C1 N3 Cu2 126.3(7) . . ?
C1 N3 N2 108.6(8) . . ?
O1 C1 N1 125.4(8) . . ?
O1 C1 N3 128.7(9) . . ?
N3 C1 N1 105.9(9) . . ?
N1 C2 H2 124.9 . . ?
N2 C2 N1 110.1(10) . . ?
N2 C2 H2 124.9 . . ?

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 N2 N3 Cu2 0.000(2) . . . . ?
Cu1 N2 N3 C1 180.000(2) . . . . ?
Cu1 N2 C2 N1 180.000(2) . . . . ?
Cu2 N3 C1 O1 0.000(3) . . . . ?
Cu2 N3 C1 N1 180.000(2) . . . . ?
Na1 O1 C1 N1 0.000(3) . . . . ?
Na1 O1 C1 N3 180.000(2) . . . . ?
N4 N1 C1 O1 0.000(3) . . . . ?
N4 N1 C1 N3 180.000(2) . . . . ?
N4 N1 C2 N2 180.000(2) . . . . ?
N2 N3 C1 O1 180.000(2) . . . . ?
N2 N3 C1 N1 0.000(2) . . . . ?
N3 N2 C2 N1 0.000(2) . . . . ?
C1 N1 N4 N4 180.000(2) . . . 17_665 ?
C1 N1 C2 N2 0.000(2) . . . . ?
C2 N1 N4 N4 0.000(3) . . . 17_665 ?
C2 N1 C1 O1 180.000(2) . . . . ?
C2 N1 C1 N3 0.000(2) . . . . ?
C2 N2 N3 Cu2 180.000(2) . . . . ?
C2 N2 N3 C1 0.000(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
