# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_[Cu(C12H26N4O2)(MeOH)2](ClO4)2(MeOH)2
_database_code_depnum_ccdc_archive 'CCDC 1912468'
loop_
_audit_author_name
_audit_author_address
'Hiroyuki Miyake'
;Osaka City University
Japan
;
_audit_update_record             
;
2019-04-26 deposited with the CCDC.	2019-11-03 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_formula_moiety         'C14 H34 Cu N4 O4, 2(Cl O4), 2(C H4 O)'
_chemical_formula_sum            'C16 H42 Cl2 Cu N4 O14'
_chemical_formula_weight         648.97

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_H-M_alt        'P 32 2 1'
_space_group_name_Hall           'P 32 2"'

_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'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'
'y, x, -z'

_cell_length_a                   8.729(9)
_cell_length_b                   8.729(9)
_cell_length_c                   33.58(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2216(5)
_cell_formula_units_Z            3
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    137
_cell_measurement_theta_min      3.0312
_cell_measurement_theta_max      27.4835
_exptl_crystal_description       Prism
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?

_exptl_crystal_density_diffrn    1.459
_exptl_crystal_F_000             1023
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.986
_shelx_estimated_absorpt_T_min   0.756
_shelx_estimated_absorpt_T_max   0.827
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8078
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_method       ω
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       
;
Mercury CCD (2x2 bin mode)
;
_diffrn_reflns_number            16969
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         3.252
_diffrn_reflns_theta_max         27.467
_diffrn_reflns_theta_full        25.241
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             3269
_reflns_number_gt                3161
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.664
_reflns_Friedel_fraction_max     0.947
_reflns_Friedel_fraction_full    0.969

_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       'CrystalClear (Rigaku Corp., 2000)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2000)'
_computing_structure_solution    'SIR2004 (Burla et al., 2004)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_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)+(0.0381P)²+0.9592P] 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 x determined using 1122 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(8)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3269
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.0971
_refine_ls_wR_factor_gt          0.0939
_refine_ls_goodness_of_fit_ref   1.277
_refine_ls_restrained_S_all      1.277
_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 0.60433(7) 1.0000 0.1667 0.02246(17) Uani 1 2 d S T P . .
Cl1 Cl 0.88647(13) 0.60178(12) 0.05909(3) 0.0315(2) Uani 1 1 d . . . . .
O1 O 0.5200(4) 0.8239(4) 0.11776(8) 0.0345(7) Uani 1 1 d . . . . .
O2 O 0.5147(4) 1.1506(4) 0.13857(9) 0.0366(7) Uani 1 1 d . . . . .
H14 H 0.4621 1.1180 0.1167 0.058(17) Uiso 1 1 d . . . . .
N2 N 0.8358(5) 1.1099(5) 0.13185(10) 0.0297(7) Uani 1 1 d . . . . .
N1 N 0.5783(5) 0.8024(5) 0.05336(11) 0.0363(8) Uani 1 1 d . . . . .
H4 H 0.6475 0.8530 0.0327 0.044 Uiso 1 1 calc R U . . .
C2 C 0.6163(5) 0.8891(5) 0.08755(12) 0.0295(8) Uani 1 1 d . . . . .
C6 C 0.9280(6) 1.0130(6) 0.14411(13) 0.0307(9) Uani 1 1 d . . . . .
H12 H 1.0539 1.0809 0.1361 0.037 Uiso 1 1 calc R U . . .
H13 H 0.8732 0.8964 0.1307 0.037 Uiso 1 1 calc R U . . .
C3 C 0.7776(5) 1.0757(5) 0.08941(11) 0.0317(9) Uani 1 1 d . . . . .
H5 H 0.7341 1.1590 0.0828 0.038 Uiso 1 1 calc R U . . .
O10 O 0.2987(5) 1.0234(5) 0.07780(12) 0.0562(11) Uani 1 1 d . . . . .
H18 H 0.2465 0.9114 0.0763 0.14(4) Uiso 1 1 d . . . . .
C5 C 0.9467(8) 1.3020(6) 0.13941(15) 0.0453(13) Uani 1 1 d . . . . .
H9 H 0.9766 1.3219 0.1678 0.068 Uiso 1 1 calc R U . . .
H10 H 0.8813 1.3617 0.1318 0.068 Uiso 1 1 calc R U . . .
H11 H 1.0555 1.3495 0.1237 0.068 Uiso 1 1 calc R U . . .
C7 C 0.4760(9) 1.2713(8) 0.15795(17) 0.0568(15) Uani 1 1 d . . . . .
H15 H 0.3657 1.2057 0.1730 0.085 Uiso 1 1 calc R U . . .
H16 H 0.4628 1.3461 0.1381 0.085 Uiso 1 1 calc R U . . .
H17 H 0.5727 1.3457 0.1762 0.085 Uiso 1 1 calc R U . . .
C1 C 0.4252(8) 0.6253(6) 0.04881(16) 0.0487(12) Uani 1 1 d . . . . .
H1 H 0.4451 0.5402 0.0637 0.073 Uiso 1 1 calc R U . . .
H2 H 0.4082 0.5928 0.0206 0.073 Uiso 1 1 calc R U . . .
H3 H 0.3195 0.6240 0.0591 0.073 Uiso 1 1 calc R U . . .
C4 C 0.9240(7) 1.1124(7) 0.05950(14) 0.0419(11) Uani 1 1 d . . . . .
H6 H 1.0255 1.2304 0.0643 0.063 Uiso 1 1 calc R U . . .
H7 H 0.8798 1.1066 0.0324 0.063 Uiso 1 1 calc R U . . .
H8 H 0.9606 1.0236 0.0626 0.063 Uiso 1 1 calc R U . . .
C8 C 0.3609(8) 1.0946(9) 0.03914(17) 0.0569(15) Uani 1 1 d . . . . .
H19 H 0.2718 1.1129 0.0256 0.085 Uiso 1 1 calc R U . . .
H20 H 0.3823 1.0119 0.0237 0.085 Uiso 1 1 calc R U . . .
H21 H 0.4713 1.2079 0.0415 0.085 Uiso 1 1 calc R U . . .
O8 O 1.028(3) 0.681(3) 0.0853(6) 0.119(11) Uani 0.4 1 d . . P A 2
O6 O 0.8010(17) 0.6136(18) 0.0933(3) 0.075(4) Uani 0.6 1 d . . P A 1
O7 O 0.870(4) 0.444(3) 0.0430(9) 0.099(10) Uani 0.4 1 d . . P A 2
O9 O 0.732(2) 0.544(4) 0.0827(8) 0.112(10) Uani 0.4 1 d . . P A 2
O4 O 0.8052(19) 0.4307(17) 0.0434(6) 0.064(4) Uani 0.6 1 d . . P A 1
O5 O 1.0633(14) 0.6511(18) 0.0694(4) 0.073(4) Uani 0.6 1 d . . P A 1
O3 O 0.8916(6) 0.7233(5) 0.02957(9) 0.0487(8) 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 O2 2.064(3) 4_675 ?
Cu1 O2 2.064(3) . ?
Cu1 N2 2.105(4) 4_675 ?
Cu1 N2 2.105(4) . ?
Cu1 O1 2.115(3) 4_675 ?
Cu1 O1 2.115(3) . ?
Cl1 O8 1.390(17) . ?
Cl1 O4 1.397(15) . ?
Cl1 O6 1.401(10) . ?
Cl1 O7 1.42(2) . ?
Cl1 O5 1.422(10) . ?
Cl1 O9 1.425(19) . ?
Cl1 O3 1.436(3) . ?
O1 C2 1.257(5) . ?
O2 C7 1.415(6) . ?
O2 H14 0.837 . ?
N2 C5 1.480(6) . ?
N2 C6 1.488(6) . ?
N2 C3 1.492(5) . ?
N1 C2 1.323(5) . ?
N1 C1 1.461(6) . ?
N1 H4 0.8800 . ?
C2 C3 1.531(6) . ?
C6 C6 1.528(9) 4_675 ?
C6 H12 0.9900 . ?
C6 H13 0.9900 . ?
C3 C4 1.528(6) . ?
C3 H5 1.0000 . ?
O10 C8 1.424(7) . ?
O10 H18 0.849 . ?
C5 H9 0.9800 . ?
C5 H10 0.9800 . ?
C5 H11 0.9800 . ?
C7 H15 0.9800 . ?
C7 H16 0.9800 . ?
C7 H17 0.9800 . ?
C1 H1 0.9800 . ?
C1 H2 0.9800 . ?
C1 H3 0.9800 . ?
C4 H6 0.9800 . ?
C4 H7 0.9800 . ?
C4 H8 0.9800 . ?
C8 H19 0.9800 . ?
C8 H20 0.9800 . ?
C8 H21 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 91.53(19) 4_675 . ?
O2 Cu1 N2 92.23(14) 4_675 4_675 ?
O2 Cu1 N2 169.19(13) . 4_675 ?
O2 Cu1 N2 169.19(13) 4_675 . ?
O2 Cu1 N2 92.23(14) . . ?
N2 Cu1 N2 85.9(2) 4_675 . ?
O2 Cu1 O1 90.18(13) 4_675 4_675 ?
O2 Cu1 O1 91.06(13) . 4_675 ?
N2 Cu1 O1 78.80(14) 4_675 4_675 ?
N2 Cu1 O1 99.88(15) . 4_675 ?
O2 Cu1 O1 91.06(13) 4_675 . ?
O2 Cu1 O1 90.17(13) . . ?
N2 Cu1 O1 99.88(14) 4_675 . ?
N2 Cu1 O1 78.80(14) . . ?
O1 Cu1 O1 178.23(18) 4_675 . ?
O4 Cl1 O6 112.6(10) . . ?
O8 Cl1 O7 111.1(16) . . ?
O4 Cl1 O5 108.0(9) . . ?
O6 Cl1 O5 108.4(8) . . ?
O8 Cl1 O9 105.9(15) . . ?
O7 Cl1 O9 104.6(17) . . ?
O8 Cl1 O3 112.1(9) . . ?
O4 Cl1 O3 109.9(8) . . ?
O6 Cl1 O3 109.4(6) . . ?
O7 Cl1 O3 113.9(13) . . ?
O5 Cl1 O3 108.4(6) . . ?
O9 Cl1 O3 108.6(12) . . ?
C2 O1 Cu1 112.7(3) . . ?
C7 O2 Cu1 124.9(3) . . ?
C7 O2 H14 111.2 . . ?
Cu1 O2 H14 120.2 . . ?
C5 N2 C6 111.3(3) . . ?
C5 N2 C3 110.8(3) . . ?
C6 N2 C3 112.2(3) . . ?
C5 N2 Cu1 110.8(3) . . ?
C6 N2 Cu1 104.8(2) . . ?
C3 N2 Cu1 106.6(2) . . ?
C2 N1 C1 122.1(4) . . ?
C2 N1 H4 119.0 . . ?
C1 N1 H4 119.0 . . ?
O1 C2 N1 121.4(4) . . ?
O1 C2 C3 120.0(4) . . ?
N1 C2 C3 118.5(4) . . ?
N2 C6 C6 109.7(3) . 4_675 ?
N2 C6 H12 109.7 . . ?
C6 C6 H12 109.7 4_675 . ?
N2 C6 H13 109.7 . . ?
C6 C6 H13 109.7 4_675 . ?
H12 C6 H13 108.2 . . ?
N2 C3 C4 114.9(4) . . ?
N2 C3 C2 107.0(3) . . ?
C4 C3 C2 115.1(3) . . ?
N2 C3 H5 106.4 . . ?
C4 C3 H5 106.4 . . ?
C2 C3 H5 106.4 . . ?
C8 O10 H18 108.4 . . ?
N2 C5 H9 109.5 . . ?
N2 C5 H10 109.5 . . ?
H9 C5 H10 109.5 . . ?
N2 C5 H11 109.5 . . ?
H9 C5 H11 109.5 . . ?
H10 C5 H11 109.5 . . ?
O2 C7 H15 109.5 . . ?
O2 C7 H16 109.5 . . ?
H15 C7 H16 109.5 . . ?
O2 C7 H17 109.5 . . ?
H15 C7 H17 109.5 . . ?
H16 C7 H17 109.5 . . ?
N1 C1 H1 109.5 . . ?
N1 C1 H2 109.5 . . ?
H1 C1 H2 109.5 . . ?
N1 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
H2 C1 H3 109.5 . . ?
C3 C4 H6 109.5 . . ?
C3 C4 H7 109.5 . . ?
H6 C4 H7 109.5 . . ?
C3 C4 H8 109.5 . . ?
H6 C4 H8 109.5 . . ?
H7 C4 H8 109.5 . . ?
O10 C8 H19 109.5 . . ?
O10 C8 H20 109.5 . . ?
H19 C8 H20 109.5 . . ?
O10 C8 H21 109.5 . . ?
H19 C8 H21 109.5 . . ?
H20 C8 H21 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 O1 C2 N1 -176.1(3) . . . . ?
Cu1 O1 C2 C3 1.6(5) . . . . ?
C1 N1 C2 O1 -1.2(6) . . . . ?
C1 N1 C2 C3 -178.9(4) . . . . ?
C5 N2 C6 C6 79.0(5) . . . 4_675 ?
C3 N2 C6 C6 -156.2(4) . . . 4_675 ?
Cu1 N2 C6 C6 -40.9(4) . . . 4_675 ?
C5 N2 C3 C4 70.8(5) . . . . ?
C6 N2 C3 C4 -54.3(5) . . . . ?
Cu1 N2 C3 C4 -168.5(3) . . . . ?
C5 N2 C3 C2 -160.1(4) . . . . ?
C6 N2 C3 C2 74.8(4) . . . . ?
Cu1 N2 C3 C2 -39.4(3) . . . . ?
O1 C2 C3 N2 26.4(5) . . . . ?
N1 C2 C3 N2 -155.9(4) . . . . ?
O1 C2 C3 C4 155.3(4) . . . . ?
N1 C2 C3 C4 -26.9(6) . . . . ?

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.088

