# 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_DATMOF1a
_database_code_depnum_ccdc_archive 'CCDC 1414256'
_audit_update_record             
;
2015-07-24 deposited with the CCDC.
2015-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Cu N10 O4'
_chemical_formula_sum            'C20 H16 Cu N10 O4'
_chemical_formula_weight         523.97

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      Orthorhombic
_space_group_IT_number           ?
_space_group_name_H-M_alt        'P b n b'
_space_group_name_Hall           ?

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

_cell_length_a                   17.7157(6)
_cell_length_b                   22.1231(8)
_cell_length_c                   25.3814(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     9947.6(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       'Block shaped'
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.700
_exptl_crystal_F_000             2136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.462
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9339
_exptl_absorpt_correction_T_max  0.9552
_exptl_absorpt_process_details   'multi-scan absorption correction'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            163610
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.0919
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.402
_diffrn_reflns_theta_max         25.414
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9132
_reflns_number_gt                7528
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0808P)²+14.5162P] 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         9132
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.1646
_refine_ls_wR_factor_gt          0.1540
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_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
Cu01 Cu 0.94383(2) 0.03615(2) 0.01442(2) 0.03434(13) Uani 1 1 d . . . . .
O4 O 1.01902(11) 0.09943(8) 0.00348(10) 0.0420(5) Uani 1 1 d . . . . .
O2 O 0.88448(10) -0.03964(8) 0.01893(8) 0.0331(4) Uani 1 1 d . . . . .
O1 O 0.98551(12) 0.02099(9) 0.08466(8) 0.0387(5) Uani 1 1 d . . . . .
O3 O 0.92009(12) 0.04084(9) -0.06151(8) 0.0395(5) Uani 1 1 d . . . . .
N7 N 0.85608(12) 0.09804(9) 0.04245(9) 0.0251(5) Uani 1 1 d . . . . .
N9 N 0.76496(13) 0.04808(10) -0.00468(10) 0.0338(6) Uani 1 1 d . . . . .
H9A H 0.7228 0.0474 -0.0214 0.041 Uiso 1 1 calc R U . . .
H9B H 0.7919 0.0158 -0.0025 0.041 Uiso 1 1 calc R U . . .
N6 N 0.82906(13) 0.19922(10) 0.06940(10) 0.0320(5) Uani 1 1 d . . . . .
N8 N 0.74360(13) 0.14693(9) 0.01272(9) 0.0292(5) Uani 1 1 d . . . . .
N2 N 1.14057(15) -0.05362(12) 0.41796(11) 0.0438(6) Uani 1 1 d . . . . .
C18 C 0.76814(15) 0.19614(11) 0.03873(11) 0.0284(6) Uani 1 1 d . . . . .
N10 N 0.93101(14) 0.14818(11) 0.10168(11) 0.0430(7) Uani 1 1 d . . . . .
H10A H 0.9420 0.1794 0.1203 0.052 Uiso 1 1 calc R U . . .
H10B H 0.9590 0.1165 0.1032 0.052 Uiso 1 1 calc R U . . .
N3 N 1.14900(17) -0.09137(12) 0.32937(11) 0.0483(7) Uani 1 1 d . . . . .
C19 C 0.87094(15) 0.14889(12) 0.07058(11) 0.0289(6) Uani 1 1 d . . . . .
C13 C 0.70943(15) 0.36033(12) 0.03410(12) 0.0332(6) Uani 1 1 d . . . . .
H13 H 0.7299 0.3982 0.0410 0.040 Uiso 1 1 calc R U . . .
C20 C 0.78810(14) 0.09795(11) 0.01739(10) 0.0250(5) Uani 1 1 d . . . . .
C16 C 0.64803(16) 0.24686(12) 0.01416(13) 0.0386(7) Uani 1 1 d . . . . .
H16 H 0.6267 0.2090 0.0086 0.046 Uiso 1 1 calc R U . . .
N4 N 1.19721(19) -0.14296(12) 0.39862(11) 0.0534(8) Uani 1 1 d . . . . .
H4A H 1.2117 -0.1703 0.3768 0.064 Uiso 1 1 calc R U . . .
H4B H 1.2062 -0.1471 0.4317 0.064 Uiso 1 1 calc R U . . .
C14 C 0.75241(16) 0.30901(12) 0.04108(14) 0.0379(7) Uani 1 1 d . . . . .
H14 H 0.8020 0.3127 0.0528 0.046 Uiso 1 1 calc R U . . .
C1 C 1.04050(16) -0.01317(13) 0.09457(12) 0.0337(6) Uani 1 1 d . . . . .
C15 C 0.72283(15) 0.25118(11) 0.03089(11) 0.0297(6) Uani 1 1 d . . . . .
C7 C 1.12225(19) -0.05513(14) 0.16620(13) 0.0430(7) Uani 1 1 d . . . . .
H7 H 1.1517 -0.0740 0.1407 0.052 Uiso 1 1 calc R U . . .
N1 N 1.08862(18) 0.00272(15) 0.34593(12) 0.0590(8) Uani 1 1 d . . . . .
C12 C 0.63503(16) 0.35517(12) 0.01663(12) 0.0333(6) Uani 1 1 d . . . . .
C2 C 1.06199(18) -0.02046(15) 0.15139(13) 0.0415(7) Uani 1 1 d . . . . .
C8 C 1.1114(2) -0.04113(16) 0.31509(13) 0.0511(9) Uani 1 1 d . . . . .
C11 C 0.58660(15) 0.41037(11) 0.01044(11) 0.0287(6) Uani 1 1 d . . . . .
C9 C 1.1036(2) -0.00472(18) 0.39835(14) 0.0534(9) Uani 1 1 d . . . . .
C10 C 1.16115(18) -0.09484(14) 0.38141(13) 0.0414(7) Uani 1 1 d . . . . .
C6 C 1.13986(19) -0.06236(15) 0.21996(13) 0.0441(8) Uani 1 1 d . . . . .
H6 H 1.1813 -0.0854 0.2301 0.053 Uiso 1 1 calc R U . . .
C17 C 0.60484(16) 0.29847(12) 0.00567(13) 0.0365(7) Uani 1 1 d . . . . .
H17 H 0.5559 0.2951 -0.0073 0.044 Uiso 1 1 calc R U . . .
C3 C 1.0173(2) 0.0066(2) 0.18972(14) 0.0714(13) Uani 1 1 d . . . . .
H3 H 0.9753 0.0290 0.1795 0.086 Uiso 1 1 calc R U . . .
N5 N 1.0832(2) 0.03714(17) 0.43163(13) 0.0717(11) Uani 1 1 d . . . . .
H5A H 1.0932 0.0332 0.4646 0.086 Uiso 1 1 calc R U . . .
H5B H 1.0597 0.0687 0.4206 0.086 Uiso 1 1 calc R U . . .
C5 C 1.0955(2) -0.03513(17) 0.25719(13) 0.0529(9) Uani 1 1 d . . . . .
C4 C 1.0340(2) 0.0010(2) 0.24229(15) 0.0704(13) Uani 1 1 d . . . . .
H4 H 1.0051 0.0208 0.2676 0.084 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
Cu01 O4 1.9522(19) . ?
Cu01 O1 1.9585(19) . ?
Cu01 O3 1.975(2) . ?
Cu01 O2 1.9824(18) . ?
Cu01 N7 2.190(2) . ?
Cu01 Cu01 2.6563(7) 5_755 ?
O4 C11 1.267(3) 3 ?
O2 C11 1.238(3) 7_755 ?
O1 C1 1.258(3) . ?
O3 C1 1.252(4) 5_755 ?
N7 C19 1.358(3) . ?
N7 C20 1.362(3) . ?
N9 C20 1.303(3) . ?
N6 C18 1.332(3) . ?
N6 C19 1.338(3) . ?
N8 C20 1.345(3) . ?
N8 C18 1.345(3) . ?
N2 C10 1.351(4) . ?
N2 C9 1.359(4) . ?
C18 C15 1.472(3) . ?
N10 C19 1.325(4) . ?
N3 C10 1.340(4) . ?
N3 C8 1.346(4) . ?
C13 C14 1.378(4) . ?
C13 C12 1.395(4) . ?
C16 C17 1.391(4) . ?
C16 C15 1.395(4) . ?
N4 C10 1.316(4) . ?
C14 C15 1.407(4) . ?
C1 O3 1.252(4) 5_755 ?
C1 C2 1.500(4) . ?
C7 C2 1.367(4) . ?
C7 C6 1.409(5) . ?
N1 C8 1.310(5) . ?
N1 C9 1.367(5) . ?
C12 C17 1.392(4) . ?
C12 C11 1.501(3) . ?
C2 C3 1.390(5) . ?
C8 C5 1.502(4) . ?
C11 O2 1.238(3) 7_765 ?
C11 O4 1.267(3) 3_455 ?
C9 N5 1.305(5) . ?
C6 C5 1.369(5) . ?
C3 C4 1.372(5) . ?
C5 C4 1.404(5) . ?

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
O4 Cu01 O1 89.72(10) . . ?
O4 Cu01 O3 88.21(10) . . ?
O1 Cu01 O3 167.78(9) . . ?
O4 Cu01 O2 167.58(8) . . ?
O1 Cu01 O2 90.14(9) . . ?
O3 Cu01 O2 89.30(9) . . ?
O4 Cu01 N7 94.72(8) . . ?
O1 Cu01 N7 94.53(8) . . ?
O3 Cu01 N7 97.64(8) . . ?
O2 Cu01 N7 97.67(8) . . ?
O4 Cu01 Cu01 83.18(6) . 5_755 ?
O1 Cu01 Cu01 82.25(6) . 5_755 ?
O3 Cu01 Cu01 85.54(6) . 5_755 ?
O2 Cu01 Cu01 84.49(6) . 5_755 ?
N7 Cu01 Cu01 176.15(6) . 5_755 ?
C11 O4 Cu01 124.18(16) 3 . ?
C11 O2 Cu01 121.74(17) 7_755 . ?
C1 O1 Cu01 125.23(19) . . ?
C1 O3 Cu01 120.65(17) 5_755 . ?
C19 N7 C20 114.7(2) . . ?
C19 N7 Cu01 123.44(17) . . ?
C20 N7 Cu01 118.36(16) . . ?
C18 N6 C19 114.8(2) . . ?
C20 N8 C18 114.8(2) . . ?
C10 N2 C9 114.6(3) . . ?
N6 C18 N8 126.2(2) . . ?
N6 C18 C15 118.6(2) . . ?
N8 C18 C15 115.3(2) . . ?
C10 N3 C8 113.1(3) . . ?
N10 C19 N6 117.9(2) . . ?
N10 C19 N7 117.3(2) . . ?
N6 C19 N7 124.7(2) . . ?
C14 C13 C12 119.7(2) . . ?
N9 C20 N8 117.4(2) . . ?
N9 C20 N7 118.7(2) . . ?
N8 C20 N7 123.9(2) . . ?
C17 C16 C15 120.9(3) . . ?
C13 C14 C15 121.3(3) . . ?
O3 C1 O1 126.3(3) 5_755 . ?
O3 C1 C2 116.8(2) 5_755 . ?
O1 C1 C2 117.0(3) . . ?
C16 C15 C14 118.2(2) . . ?
C16 C15 C18 120.2(2) . . ?
C14 C15 C18 121.6(2) . . ?
C2 C7 C6 120.2(3) . . ?
C8 N1 C9 115.6(3) . . ?
C17 C12 C13 120.0(2) . . ?
C17 C12 C11 119.5(2) . . ?
C13 C12 C11 120.5(2) . . ?
C7 C2 C3 119.6(3) . . ?
C7 C2 C1 121.5(3) . . ?
C3 C2 C1 118.8(3) . . ?
N1 C8 N3 127.1(3) . . ?
N1 C8 C5 117.5(3) . . ?
N3 C8 C5 115.4(3) . . ?
O2 C11 O4 126.3(2) 7_765 3_455 ?
O2 C11 C12 118.2(2) 7_765 . ?
O4 C11 C12 115.5(2) 3_455 . ?
N5 C9 N2 117.5(3) . . ?
N5 C9 N1 119.4(3) . . ?
N2 C9 N1 123.1(3) . . ?
N4 C10 N3 116.8(3) . . ?
N4 C10 N2 116.7(3) . . ?
N3 C10 N2 126.5(3) . . ?
C5 C6 C7 119.4(3) . . ?
C16 C17 C12 119.8(3) . . ?
C4 C3 C2 121.3(3) . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 C8 122.0(3) . . ?
C4 C5 C8 117.3(3) . . ?
C3 C4 C5 118.7(3) . . ?

_refine_diff_density_max         1.273
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.079
# 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 -0.003 0.043 0.506 6514 2359 ' '
_platon_squeeze_details          
;
;

