# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_smp-30
_database_code_depnum_ccdc_archive 'CCDC 1908793'
loop_
_audit_author_name
_audit_author_address
'Christoph Janiak'
;University of Duesseldorf
Germany
;
_audit_update_record             
;
2019-05-08 deposited with the CCDC.	2019-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H24 Cu N6 O6'
_chemical_formula_weight         495.98

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'

# start Validation Reply Form
_vrf_THETM01_smp-30              
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The porous metal-organic framework (MOF) structure contains 
solvent-filled voids of about 969 Angstrom^3^ out of the unit cell 
volume of 2120 Angstrom^3.
Like in many other porous MOF structures the crystal was quite small 
in size and did not diffract above a certain threshhold. Here, this 
crystal did only diffract until theta = 20.5 deg for
Mo-Kalpha radiation instead of the expected minimum of 25 deg.
;
_vrf_PLAT250_smp-30              
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        4.4 Note  
RESPONSE: Due to poor data set quality no better model for the disorder of 
the structure could be applied. 
;
_vrf_PLAT341_smp-30              
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01717 Ang.  
RESPONSE: The crystal did only diffract until theta = 20.5 deg., 
which affects the dataset quality.
;
# end Validation Reply Form

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.7515(16)
_cell_length_b                   12.8834(16)
_cell_length_c                   13.5198(16)
_cell_angle_alpha                90
_cell_angle_beta                 107.355(7)
_cell_angle_gamma                90
_cell_volume                     2120.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    586
_cell_measurement_theta_min      2.234
_cell_measurement_theta_max      18.216

_exptl_crystal_description       pillar
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_F_000             1028
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.004
_exptl_crystal_size_min          0.004
_exptl_absorpt_coefficient_mu    1.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6270
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7626
_diffrn_reflns_av_unetI/netI     0.1326
_diffrn_reflns_av_R_equivalents  0.1177
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.673
_diffrn_reflns_theta_max         20.523
_diffrn_reflns_theta_full        20.523
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2129
_reflns_number_gt                1172
_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.
 
 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.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4.5 (Brandenburg, 2018)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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.,SQUEEZE
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0851P)²] 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         2129
_refine_ls_number_parameters     248
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1311
_refine_ls_R_factor_gt           0.0672
_refine_ls_wR_factor_ref         0.1756
_refine_ls_wR_factor_gt          0.1474
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.998
_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
Cu Cu 0.08779(9) 0.56271(9) 0.53259(10) 0.0496(6) Uani 1 1 d . . . . .
O1 O 0.1365(6) 0.4897(6) 0.4297(6) 0.062(2) Uani 1 1 d . . . . .
O2 O -0.0090(6) 0.3817(5) 0.3742(5) 0.048(2) Uani 1 1 d . . . . .
O3 O -0.0048(5) 0.1563(5) 0.0758(5) 0.051(2) Uani 1 1 d . . . . .
O4 O 0.1443(6) 0.0514(6) 0.1256(6) 0.068(2) Uani 1 1 d . . . . .
O5 O 0.9454(8) 0.1102(8) 0.3945(11) 0.137(5) Uani 1 1 d . . . . .
N1 N 0.7705(6) 0.3406(7) 0.4031(7) 0.061(3) Uani 1 1 d . U . . .
N2 N 0.7789(8) 0.2459(8) 0.3692(9) 0.103(4) Uani 1 1 d . U . . .
H2N H 0.842022 0.216536 0.372076 0.124 Uiso 1 1 calc R U . . .
N3 N 0.4896(8) 0.2515(8) 0.3042(8) 0.086(4) Uani 1 1 d . . . . .
N4 N 0.4349(7) 0.3226(7) 0.3266(8) 0.069(3) Uani 1 1 d . . . . .
N5 N 1.1220(11) 0.0683(12) 0.4328(11) 0.127(5) Uani 1 1 d . . . . .
C1 C 0.1462(10) 0.3540(9) 0.3254(9) 0.063(4) Uani 1 1 d . . . . .
C2 C 0.0930(9) 0.2792(8) 0.2511(9) 0.051(3) Uani 1 1 d . . . . .
H2 H 0.015160 0.274161 0.232370 0.061 Uiso 1 1 calc R U . . .
C3 C 0.1493(9) 0.2131(9) 0.2046(9) 0.057(3) Uani 1 1 d . . . . .
C4 C 0.2662(9) 0.2240(9) 0.2295(9) 0.064(3) Uani 1 1 d . . . . .
H4 H 0.307534 0.178301 0.200410 0.077 Uiso 1 1 calc R U . . .
C5 C 0.3178(9) 0.3023(9) 0.2965(10) 0.057(3) Uani 1 1 d . . . . .
C6 C 0.2602(9) 0.3647(9) 0.3434(9) 0.065(4) Uani 1 1 d . . . . .
H6 H 0.298268 0.417174 0.389620 0.078 Uiso 1 1 calc R U . . .
C7 C 0.0855(10) 0.4154(8) 0.3777(9) 0.051(3) Uani 1 1 d . . . . .
C8 C 0.0910(10) 0.1320(9) 0.1331(10) 0.061(3) Uani 1 1 d . . . . .
C9 C 0.6205(10) 0.4648(8) 0.4002(11) 0.098(5) Uani 1 1 d . . . . .
H9A H 0.582175 0.460014 0.452985 0.146 Uiso 1 1 calc R U . . .
H9B H 0.569468 0.489967 0.335104 0.146 Uiso 1 1 calc R U . . .
H9C H 0.682253 0.513233 0.423499 0.146 Uiso 1 1 calc R U . . .
C10 C 0.6634(9) 0.3579(8) 0.3829(9) 0.063(3) Uani 1 1 d . U . . .
C11 C 0.6042(9) 0.2715(10) 0.3378(11) 0.085(4) Uani 1 1 d . U . . .
C12 C 0.6782(10) 0.1972(11) 0.3286(14) 0.124(7) Uani 1 1 d . U . . .
C13 C 0.6665(12) 0.0895(12) 0.2871(19) 0.224(13) Uani 1 1 d . . . . .
H13A H 0.639284 0.091599 0.211280 0.336 Uiso 1 1 calc R U . . .
H13B H 0.614328 0.051257 0.313935 0.336 Uiso 1 1 calc R U . . .
H13C H 0.738068 0.054748 0.308856 0.336 Uiso 1 1 calc R U . . .
C14 C 1.0386(18) 0.1195(16) 0.432(2) 0.211(14) Uani 1 1 d . . . . .
H14 H 1.056400 0.181180 0.471856 0.253 Uiso 1 1 calc R U . . .
C15 C 1.119(2) -0.0292(11) 0.3774(17) 0.237(14) Uani 1 1 d . . . . .
H15A H 1.115214 -0.087238 0.423045 0.356 Uiso 1 1 calc R U . . .
H15B H 1.185616 -0.035569 0.355845 0.356 Uiso 1 1 calc R U . . .
H15C H 1.054282 -0.030326 0.316118 0.356 Uiso 1 1 calc R U . . .
C16 C 1.2383(17) 0.1014(16) 0.4856(18) 0.229(12) Uani 1 1 d . . . . .
H16A H 1.238832 0.172995 0.510206 0.344 Uiso 1 1 calc R U . . .
H16B H 1.281240 0.097167 0.436507 0.344 Uiso 1 1 calc R U . . .
H16C H 1.270759 0.055500 0.544669 0.344 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
Cu O1 1.929(8) . ?
Cu O4 1.929(8) 4_566 ?
Cu O3 1.948(6) 2 ?
Cu O2 1.966(7) 3_566 ?
Cu N1 2.154(8) 3_666 ?
Cu Cu 2.687(2) 3_566 ?
O1 C7 1.250(11) . ?
O2 C7 1.267(12) . ?
O3 C8 1.275(13) . ?
O4 C8 1.262(12) . ?
O5 C14 1.15(2) . ?
N1 N2 1.319(11) . ?
N1 C10 1.329(12) . ?
N2 C12 1.386(14) . ?
N2 H2N 0.8800 . ?
N3 N4 1.242(11) . ?
N3 C11 1.419(13) . ?
N4 C5 1.449(12) . ?
N5 C14 1.248(18) . ?
N5 C15 1.457(19) . ?
N5 C16 1.50(2) . ?
C1 C6 1.406(14) . ?
C1 C2 1.410(13) . ?
C1 C7 1.433(14) . ?
C2 C3 1.381(13) . ?
C2 H2 0.9500 . ?
C3 C4 1.433(13) . ?
C3 C8 1.466(14) . ?
C4 C5 1.384(13) . ?
C4 H4 0.9500 . ?
C5 C6 1.366(13) . ?
C6 H6 0.9500 . ?
C9 C10 1.526(13) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.381(14) . ?
C11 C12 1.376(15) . ?
C12 C13 1.487(17) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
O1 Cu O4 87.7(3) . 4_566 ?
O1 Cu O3 88.8(3) . 2 ?
O4 Cu O3 167.3(3) 4_566 2 ?
O1 Cu O2 167.4(3) . 3_566 ?
O4 Cu O2 91.3(3) 4_566 3_566 ?
O3 Cu O2 89.4(3) 2 3_566 ?
O1 Cu N1 99.3(3) . 3_666 ?
O4 Cu N1 94.2(3) 4_566 3_666 ?
O3 Cu N1 98.5(3) 2 3_666 ?
O2 Cu N1 93.4(3) 3_566 3_666 ?
O1 Cu Cu 83.5(2) . 3_566 ?
O4 Cu Cu 82.4(2) 4_566 3_566 ?
O3 Cu Cu 85.0(2) 2 3_566 ?
O2 Cu Cu 83.9(2) 3_566 3_566 ?
N1 Cu Cu 175.6(3) 3_666 3_566 ?
C7 O1 Cu 123.6(7) . . ?
C7 O2 Cu 120.9(7) . 3_566 ?
C8 O3 Cu 120.8(7) . 2_545 ?
C8 O4 Cu 125.0(7) . 4_565 ?
N2 N1 C10 105.6(9) . . ?
N2 N1 Cu 122.0(7) . 3_666 ?
C10 N1 Cu 132.3(7) . 3_666 ?
N1 N2 C12 113.3(10) . . ?
N1 N2 H2N 123.4 . . ?
C12 N2 H2N 123.4 . . ?
N4 N3 C11 112.8(10) . . ?
N3 N4 C5 113.9(10) . . ?
C14 N5 C15 124(2) . . ?
C14 N5 C16 125(2) . . ?
C15 N5 C16 111.0(16) . . ?
C6 C1 C2 116.4(12) . . ?
C6 C1 C7 122.9(11) . . ?
C2 C1 C7 120.8(11) . . ?
C3 C2 C1 122.6(11) . . ?
C3 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
C2 C3 C4 118.6(11) . . ?
C2 C3 C8 120.6(11) . . ?
C4 C3 C8 120.8(11) . . ?
C5 C4 C3 118.9(11) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C6 C5 C4 121.0(10) . . ?
C6 C5 N4 114.6(10) . . ?
C4 C5 N4 124.3(11) . . ?
C5 C6 C1 122.2(11) . . ?
C5 C6 H6 118.9 . . ?
C1 C6 H6 118.9 . . ?
O1 C7 O2 127.8(10) . . ?
O1 C7 C1 115.7(11) . . ?
O2 C7 C1 116.1(10) . . ?
O4 C8 O3 126.5(11) . . ?
O4 C8 C3 117.4(11) . . ?
O3 C8 C3 115.6(11) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C11 110.4(10) . . ?
N1 C10 C9 120.9(10) . . ?
C11 C10 C9 128.4(10) . . ?
C12 C11 C10 107.5(10) . . ?
C12 C11 N3 120.9(11) . . ?
C10 C11 N3 131.6(11) . . ?
C11 C12 N2 103.2(11) . . ?
C11 C12 C13 133.5(12) . . ?
N2 C12 C13 123.3(12) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 N5 136(3) . . ?
O5 C14 H14 112.2 . . ?
N5 C14 H14 112.2 . . ?
N5 C15 H15A 109.5 . . ?
N5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N5 C16 H16A 109.5 . . ?
N5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C10 N1 N2 C12 -1.7(17) . . . . ?
Cu N1 N2 C12 -178.6(11) 3_666 . . . ?
C11 N3 N4 C5 -177.8(11) . . . . ?
C6 C1 C2 C3 5.6(16) . . . . ?
C7 C1 C2 C3 -175.0(10) . . . . ?
C1 C2 C3 C4 -2.8(16) . . . . ?
C1 C2 C3 C8 175.8(10) . . . . ?
C2 C3 C4 C5 -2.0(16) . . . . ?
C8 C3 C4 C5 179.4(11) . . . . ?
C3 C4 C5 C6 3.8(18) . . . . ?
C3 C4 C5 N4 -179.0(11) . . . . ?
N3 N4 C5 C6 163.6(11) . . . . ?
N3 N4 C5 C4 -13.8(17) . . . . ?
C4 C5 C6 C1 -0.8(18) . . . . ?
N4 C5 C6 C1 -178.3(11) . . . . ?
C2 C1 C6 C5 -3.8(17) . . . . ?
C7 C1 C6 C5 176.8(11) . . . . ?
Cu O1 C7 O2 7.8(16) . . . . ?
Cu O1 C7 C1 -164.5(7) . . . . ?
Cu O2 C7 O1 -6.6(15) 3_566 . . . ?
Cu O2 C7 C1 165.6(7) 3_566 . . . ?
C6 C1 C7 O1 9.9(16) . . . . ?
C2 C1 C7 O1 -169.4(10) . . . . ?
C6 C1 C7 O2 -163.3(10) . . . . ?
C2 C1 C7 O2 17.4(15) . . . . ?
Cu O4 C8 O3 -6.3(18) 4_565 . . . ?
Cu O4 C8 C3 -177.0(7) 4_565 . . . ?
Cu O3 C8 O4 3.2(17) 2_545 . . . ?
Cu O3 C8 C3 174.1(7) 2_545 . . . ?
C2 C3 C8 O4 -152.2(11) . . . . ?
C4 C3 C8 O4 26.4(17) . . . . ?
C2 C3 C8 O3 36.0(16) . . . . ?
C4 C3 C8 O3 -145.4(11) . . . . ?
N2 N1 C10 C11 1.4(15) . . . . ?
Cu N1 C10 C11 177.8(9) 3_666 . . . ?
N2 N1 C10 C9 -173.0(12) . . . . ?
Cu N1 C10 C9 3.4(18) 3_666 . . . ?
N1 C10 C11 C12 -0.6(17) . . . . ?
C9 C10 C11 C12 173.3(14) . . . . ?
N1 C10 C11 N3 178.9(14) . . . . ?
C9 C10 C11 N3 -7(3) . . . . ?
N4 N3 C11 C12 173.8(14) . . . . ?
N4 N3 C11 C10 -6(2) . . . . ?
C10 C11 C12 N2 -0.4(18) . . . . ?
N3 C11 C12 N2 -179.9(14) . . . . ?
C10 C11 C12 C13 180(2) . . . . ?
N3 C11 C12 C13 0(3) . . . . ?
N1 N2 C12 C11 1.3(18) . . . . ?
N1 N2 C12 C13 -178.9(17) . . . . ?
C15 N5 C14 O5 0(4) . . . . ?
C16 N5 C14 O5 177(2) . . . . ?

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
_geom_hbond_publ_flag
N2 H2N O5 0.88 1.86 2.692(14) 156.5 . yes
C9 H9C O1 0.98 2.56 3.314(15) 133.9 3_666 yes
C9 H9C O4 0.98 2.54 3.314(15) 135.9 2_655 yes
C13 H13C O5 0.98 2.65 3.427(18) 136.6 . yes

_refine_diff_density_max         0.436
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.080



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dimethylformamide'
####################################################################### 
# 
# 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_Zn-IsoAzoPyz
_database_code_depnum_ccdc_archive 'CCDC 1908794'
loop_
_audit_author_name
_audit_author_address
'Christoph Janiak'
;University of Duesseldorf
Germany
;
_audit_update_record             
;
2019-05-08 deposited with the CCDC.	2019-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H24 N6 O6 Zn'
_chemical_formula_weight         497.81

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

# start Validation Reply Form
_vrf_THETM01_Zn-IsoAzoPyz        
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: The porous metal-organic framework (MOF) structure contains 
solvent-filled voids of about 1088 Angstrom^3^ out of the unit cell 
volume of 2241 Angstrom^3^.
Like in many other porous MOFs the crystal was quite small in size and 
did not diffract above a certain threshhold. Here, this crystal did only 
diffract until theta = 24.1 deg for Mo-Kalpha radiation instead of the 
expected minimum of 25 deg.  
;
# end Validation Reply Form

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.9493(11)
_cell_length_b                   13.0923(12)
_cell_length_c                   14.0511(13)
_cell_angle_alpha                90
_cell_angle_beta                 109.842(5)
_cell_angle_gamma                90
_cell_volume                     2240.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4964
_cell_measurement_theta_min      2.189
_cell_measurement_theta_max      22.538

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.144
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6718
_exptl_absorpt_correction_T_max  0.7450
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2015)'

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans, π scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26956
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.672
_diffrn_reflns_theta_max         24.117
_diffrn_reflns_theta_full        24.117
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3490
_reflns_number_gt                2761
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4.5 (Crystal Impact, 2018)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0676P)²+2.3445P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3490
_refine_ls_number_parameters     306
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1196
_refine_ls_wR_factor_gt          0.1105
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.002

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_s