# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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 
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data_rls206s
_database_code_depnum_ccdc_archive 'CCDC 1912757'
loop_
_audit_author_name
_audit_author_address
'Rebecca Siegelman'
;University of California, Berkeley
United States of America
;
_audit_update_record             
;
2019-04-29 deposited with the CCDC.	2022-09-12 downloaded from the CCDC.
;
_audit_creation_date             2019-02-15
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            Zn2(dobpdc)(ee-2)0.902(ee-2-CO2)0.690
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24.24 H31.47 N3.18 O7.38 Zn2'
_chemical_formula_sum            'C24.24 H31.47 N3.18 O7.38 Zn2'
_chemical_formula_weight         616.33
_chemical_absolute_configuration ?
_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 0.0040 0.0020
'ANOMDisVal Program in PLATON Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7-13'
H H 0.0000 0.0000
'ANOMDisVal Program in PLATON Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7-13'
N N 0.0080 0.0040
'ANOMDisVal Program in PLATON Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7-13'
O O 0.0130 0.0070
'ANOMDisVal Program in PLATON Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7-13'
Zn Zn 0.2280 1.6720
'ANOMDisVal Program in PLATON Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7-13'

_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      trigonal
_space_group_IT_number           152
_space_group_name_H-M_alt        'P 31 2 1'
_space_group_name_Hall           'P 31 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'y, x, -z'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'

_cell_length_a                   21.5982(10)
_cell_length_b                   21.5982(10)
_cell_length_c                   6.9071(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2790.4(3)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    9873
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.466
_cell_measurement_theta_min      2.954
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.895
_exptl_absorpt_coefficient_mu    1.418
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_correction_T_min  0.798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1850 before and 0.0672 after correction.
The Ratio of minimum to maximum transmission is 0.8448.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.112
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             965
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
X-ray diffraction analyses were performed on single crystals coated with
 Paratone-N oil and mounted on MiTeGen loops. Crystals were frozen at a
 temperature of 100 K by an Oxford Cryosystems Cyrostream using N2 during
 the experiments. Data was collected at Beamline 12.2.1 at the Advanced
 Light Source, Lawrence Berkeley National Laboratory using synchrotron
 radiation (lamda = 0.7288 angstrom) and a Bruker D8 Diffractometer with 
 a Bruker PHOTON II CMOS detector.

Crystals of ee-2-Zn2(dobpdc) (dobpdc4- = 
4,4'-dioxidobiphenyl-3,3'-dicarboxylate, ee-2 = N,N-diethylethylenediamine) 
were activated for 1 h at 100 C under vacuum (<10 microbar) and then 
transferred to the analysis port of a Micromeritics ASAP2420 gas sorption 
analyzer. The crystals were placed under 1100 mbar of CO2 for 5 min at room 
temperature. The glass adsorption tube was then sealed under this CO2 
atmosphere, removed from the instrument, and stored over dry ice for 28 h. 
Immediately after removing the seal on the glass adsorption tube, the 
crystals were coated with Paratone oil, and a single crystal was rapidly 
mounted on a MiTeGen loop and frozen at a temperature of 100 K in a cryostream 
of N2.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            55047
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.930
_diffrn_reflns_theta_max         29.907
_diffrn_reflns_theta_min         1.934
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 with PHOTON II detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7288
_diffrn_source                   
;
Advanced Light Source, station 12.2.1
;
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4509
_reflns_number_total             5009
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker-AXS, Madison WI, 2016)'
_computing_data_collection       'Bruker APEX3 Bruker-AXS, Madison WI'
_computing_data_reduction        'SAINT V8.38A (Bruker-AXS, Madison WI, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.495(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         5009
_refine_ls_number_restraints     95
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+1.0865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0906
_refine_special_details          
;Refined as a 2-component inversion twin.
Thermal parameters were refined anisotropically for all non-hydrogen atoms. 
All hydrogen atoms were placed in ideal positions and refined using a 
riding model. The structure shows CO2 reacted with a metal-organic 
framework appended with N,N-diethylethylenediamine to form ammonium carbamate 
chains along the pore axis. The ammonium carbamate chains (part -1) freely 
refined to an occupancy of 0.345(5). In addition, unreacted diamine was 
resolved in the structure (part -2) and freely refined to an occupancy of 
0.451(8). These occupancies were fixed in the final refinement. Additionally, 
the occupancy of atom O4 (the bound oxygen atom of the carbamate) was fixed as 
1 - the occupancy of the unreacted diamine = 0.549 to account for water, 
solvent, or unreacted CO2  at the open Zn(II) coordination sites not bound to  
carbamate groups or unreacted diamine. This decision was made on the basis of 
free refinement of the bound nitrogen and oxygen atoms, which gave occupancies 
of N3 = 0.41(5) (within error of the occupancy of unreacted diamine) and O4 = 
0.55(5) (within error of 1 - the occupancy of unreacted diamine), respectively. 

To model the disorder, the following distance and displacement parameter 
restraints were used: 
SADI for 1,2 distances of C-C bonds in the ethyl groups of the diamine, 
SADI for 1,2 distances of the C-N bonds of the tertiary amine in part -2, 
DFIX for the C-N bonds of the ammonium, and
RIGU and SIMU for the unreacted diamine (part -2)

Four instances of OMIT were used (OMIT 0 1 0, OMIT -1 1 1, OMIT 0 3 0, 
OMIT -4 4 2). These reflections were suspected to be affected by the beamstop.,Twin
;
_vrf_PLAT213_rls206s             
;
PROBLEM: Atom C18             has ADP max/min Ratio .....        4.3 prolat
RESPONSE: The disorder of the unreacted diamine bound to the Zn(II) centers  
of the framework results in large ratios in the anisotropic displacement 
parameters of the constituent atoms.
;
_vrf_PLAT220_rls206s             
;
PROBLEM: Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range       10.0 Ratio 
RESPONSE: The disorder of the unreacted diamine bound to the Zn(II) centers  
of the framework results in large ratios in the anisotropic displacement 
parameters of the constituent atoms.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.505(18)
 0.495(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H,H,H) groups, All N(H)
  groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 N2-C11 = N2-C13
 1.49 with sigma of 0.02
 C20-C19 \\sim C18-C17 \\sim C12-C11 \\sim C14-C13
 with sigma of 0.02
 N4-C19 \\sim N4-C17 \\sim N4-C16
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
N3 \\sim N4 \\sim C15 \\sim C16 \\sim C17 \\sim C18 \\sim C19 \\sim C20: within
2A with sigma of 0.04 and sigma for terminal atoms of 0.08
5. Rigid body (RIGU) restrains
 N3, N4, C15, C16, C17, C18, C19, C20
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: N3(0.451) H3A(0.451) H3B(0.451) N4(0.451) C15(0.451) H15A(0.451)
 H15B(0.451) C16(0.451) H16A(0.451) H16B(0.451) C17(0.451) H17A(0.451)
 H17B(0.451) C18(0.451) H18A(0.2255) H18E(0.2255) H18D(0.2255) H18B(0.2255)
 H18C(0.2255) H18F(0.2255) C19(0.451) H19A(0.451) H19B(0.451) C20(0.451)
 H20A(0.2255) H20B(0.2255) H20C(0.2255) H20D(0.2255) H20E(0.2255) H20F(0.2255)
 O4(0.549) O5(0.345) N1(0.345) H1(0.345) N2(0.345) H2(0.345) C8(0.345)
 C9(0.345) H9A(0.345) H9B(0.345) C10(0.345) H10A(0.345) H10B(0.345) C11(0.345)
 H11A(0.345) H11B(0.345) C12(0.345) H12A(0.345) H12B(0.345) H12C(0.345)
 C13(0.345) H13A(0.345) H13B(0.345) C14(0.345) H14A(0.345) H14B(0.345)
 H14C(0.345)
7.a Ternary CH refined with riding coordinates:
 N2(H2)
7.b Secondary CH2 refined with riding coordinates:
 N3(H3A,H3B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C19(H19A,H19B),
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B)
7.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), N1(H1)
7.d Disordered Me refined with riding coordinates:
 C18(H18A,H18E,H18D,H18B,H18C,H18F), C20(H20A,H20B,H20C,H20D,H20E,H20F)
7.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   diffmap
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
Zn1 Zn 0.27703(2) 0.60916(2) 0.64559(4) 0.02002(11) Uani 1 1 d . . . . .
O1 O 0.34410(15) 0.58449(13) 0.7882(3) 0.0219(5) Uani 1 1 d . . . . .
O2 O 0.36180(12) 0.64813(15) 0.4349(3) 0.0210(4) Uani 1 1 d . . . . .
O3 O 0.41012(13) 0.61623(13) 0.1979(3) 0.0212(5) Uani 1 1 d . . . . .
C1 C 0.37729(19) 0.55404(19) 0.7024(4) 0.0207(7) Uani 1 1 d . . . . .
C2 C 0.39754(18) 0.56314(18) 0.5040(4) 0.0195(6) Uani 1 1 d . . . . .
C3 C 0.43067(19) 0.52630(19) 0.4307(4) 0.0220(7) Uani 1 1 d . . . . .
H3 H 0.443213 0.531855 0.297407 0.026 Uiso 1 1 calc R . . . .
C4 C 0.4460(2) 0.48246(19) 0.5413(4) 0.0228(7) Uani 1 1 d . . . . .
C5 C 0.4269(2) 0.4750(2) 0.7370(4) 0.0270(7) Uani 1 1 d . . . . .
H5 H 0.436848 0.445497 0.817889 0.032 Uiso 1 1 calc R . . . .
C6 C 0.3935(2) 0.5100(2) 0.8148(4) 0.0262(7) Uani 1 1 d . . . . .
H6 H 0.381364 0.503963 0.948300 0.031 Uiso 1 1 calc R . . . .
C7 C 0.38836(18) 0.61177(19) 0.3706(4) 0.0192(6) Uani 1 1 d . . . . .
N3 N 0.2138(15) 0.5081(9) 0.508(3) 0.035(3) Uani 0.451 1 d . U P A -2
H3A H 0.172164 0.504965 0.468049 0.042 Uiso 0.451 1 calc R . P A -2
H3B H 0.237403 0.506564 0.400971 0.042 Uiso 0.451 1 calc R . P A -2
N4 N 0.1726(8) 0.3794(7) 0.342(2) 0.085(4) Uani 0.451 1 d D U P A -2
C15 C 0.1964(6) 0.4459(4) 0.6268(13) 0.0342(18) Uani 0.451 1 d . U P A -2
H15A H 0.177293 0.450241 0.753168 0.041 Uiso 0.451 1 calc R . P A -2
H15B H 0.240301 0.443397 0.651334 0.041 Uiso 0.451 1 calc R . P A -2
C16 C 0.1430(7) 0.3801(6) 0.529(2) 0.051(3) Uani 0.451 1 d D U P A -2
H16A H 0.133902 0.337440 0.604706 0.061 Uiso 0.451 1 calc R . P A -2
H16B H 0.097434 0.379975 0.513314 0.061 Uiso 0.451 1 calc R . P A -2
C17 C 0.2263(12) 0.3571(15) 0.371(4) 0.148(8) Uani 0.451 1 d D U P A -2
H17A H 0.201675 0.306308 0.410664 0.177 Uiso 0.451 1 calc R . P A -2
H17B H 0.258832 0.385688 0.477184 0.177 Uiso 0.451 1 calc R . P A -2
C18 C 0.2702(13) 0.3661(16) 0.191(5) 0.26(2) Uani 0.451 1 d D U P A -2
H18A H 0.304803 0.350480 0.219045 0.317 Uiso 0.2255 1 calc R . P A -2
H18E H 0.238512 0.337062 0.086188 0.317 Uiso 0.2255 1 calc R . P A -2
H18D H 0.295704 0.416490 0.152748 0.317 Uiso 0.2255 1 calc R . P A -2
H18B H 0.254543 0.385541 0.086276 0.317 Uiso 0.2255 1 calc R . P A -2
H18C H 0.320834 0.398959 0.219133 0.317 Uiso 0.2255 1 calc R . P A -2
H18F H 0.263642 0.319531 0.152572 0.317 Uiso 0.2255 1 calc R . P A -2
C19 C 0.1147(13) 0.3382(11) 0.201(3) 0.125(8) Uani 0.451 1 d D U P A -2
H19A H 0.082345 0.290110 0.255235 0.150 Uiso 0.451 1 calc R . P A -2
H19B H 0.135843 0.332048 0.080927 0.150 Uiso 0.451 1 calc R . P A -2
C20 C 0.0706(18) 0.3744(17) 0.152(5) 0.201(16) Uani 0.451 1 d D U P A -2
H20A H 0.033208 0.344860 0.058390 0.242 Uiso 0.2255 1 calc R . P A -2
H20B H 0.048543 0.379672 0.269939 0.242 Uiso 0.2255 1 calc R . P A -2
H20C H 0.102068 0.421631 0.095542 0.242 Uiso 0.2255 1 calc R . P A -2
H20D H 0.089338 0.419249 0.224191 0.242 Uiso 0.2255 1 calc R . P A -2
H20E H 0.074003 0.384437 0.012642 0.242 Uiso 0.2255 1 calc R . P A -2
H20F H 0.020478 0.342478 0.187039 0.242 Uiso 0.2255 1 calc R . P A -2
O4 O 0.2131(11) 0.5030(9) 0.5586(18) 0.061(5) Uani 0.549 1 d . . P A -1
O5 O 0.1672(9) 0.3914(6) 0.4264(16) 0.065(4) Uani 0.345 1 d . . P A -1
N1 N 0.2322(6) 0.4936(6) 0.2541(14) 0.041(3) Uani 0.345 1 d . . P A -1
H1 H 0.258619 0.540517 0.255946 0.049 Uiso 0.345 1 calc R . P A -1
N2 N 0.1335(7) 0.3878(6) -0.1821(16) 0.051(3) Uani 0.345 1 d D . P A -1
H2 H 0.165176 0.425046 -0.277588 0.061 Uiso 0.345 1 calc R . P A -1
C8 C 0.2041(8) 0.4607(6) 0.4114(17) 0.042(3) Uani 0.345 1 d . . P A -1
C9 C 0.2220(7) 0.4565(7) 0.0735(16) 0.038(3) Uani 0.345 1 d . . P A -1
H9A H 0.233847 0.418067 0.090158 0.046 Uiso 0.345 1 calc R . P A -1
H9B H 0.254617 0.490235 -0.025471 0.046 Uiso 0.345 1 calc R . P A -1
C10 C 0.1467(8) 0.4251(7) 0.0068(17) 0.041(3) Uani 0.345 1 d . . P A -1
H10A H 0.114538 0.390769 0.105400 0.049 Uiso 0.345 1 calc R . P A -1
H10B H 0.134759 0.463636 -0.004781 0.049 Uiso 0.345 1 calc R . P A -1
C11 C 0.1570(9) 0.3317(8) -0.1820(19) 0.057(4) Uani 0.345 1 d D . P A -1
H11A H 0.145836 0.307840 -0.309999 0.068 Uiso 0.345 1 calc R . P A -1
H11B H 0.209517 0.356224 -0.164766 0.068 Uiso 0.345 1 calc R . P A -1
C12 C 0.1226(13) 0.2756(9) -0.028(2) 0.076(6) Uani 0.345 1 d D . P A -1
H12A H 0.104882 0.228211 -0.085676 0.114 Uiso 0.345 1 calc GR . P A -1
H12B H 0.082645 0.278456 0.029381 0.114 Uiso 0.345 1 calc GR . P A -1
H12C H 0.157860 0.283531 0.072350 0.114 Uiso 0.345 1 calc GR . P A -1
C13 C 0.0563(8) 0.3588(8) -0.2555(18) 0.055(4) Uani 0.345 1 d D . P A -1
H13A H 0.050671 0.333122 -0.378726 0.066 Uiso 0.345 1 calc R . P A -1
H13B H 0.023094 0.323470 -0.160475 0.066 Uiso 0.345 1 calc R . P A -1
C14 C 0.0338(8) 0.4141(8) -0.289(2) 0.061(4) Uani 0.345 1 d D . P A -1
H14A H 0.006997 0.403644 -0.410101 0.092 Uiso 0.345 1 calc GR . P A -1
H14B H 0.076412 0.461738 -0.296087 0.092 Uiso 0.345 1 calc GR . P A -1
H14C H 0.003576 0.412736 -0.181070 0.092 Uiso 0.345 1 calc GR . P A -1


_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
Zn1 Zn1 3.1360(4) 2_665 ?
Zn1 Zn1 3.1360(4) 3_564 ?
Zn1 O1 2.044(2) 3_564 ?
Zn1 O1 2.031(3) . ?
Zn1 O2 2.186(3) 2_665 ?
Zn1 O2 2.154(2) . ?
Zn1 O3 2.042(2) 3_565 ?
Zn1 N3 2.133(18) . ?
Zn1 O4 2.088(17) . ?
O1 C1 1.330(4) . ?
O2 C7 1.262(4) . ?
O3 C7 1.268(4) . ?
C1 C2 1.422(4) . ?
C1 C6 1.401(5) . ?
C2 C3 1.404(5) . ?
C2 C7 1.483(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(5) . ?
C4 C4 1.477(7) 4_556 ?
C4 C5 1.399(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(5) . ?
C6 H6 0.9500 . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 C15 1.454(18) . ?
N4 C16 1.441(15) . ?
N4 C17 1.48(2) . ?
N4 C19 1.480(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.473(13) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.51(2) . ?
C18 H18A 0.9800 . ?
C18 H18E 0.9800 . ?
C18 H18D 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 H18F 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.54(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 H20D 0.9800 . ?
C20 H20E 0.9800 . ?
C20 H20F 0.9800 . ?
O4 C8 1.315(18) . ?
O5 C8 1.301(17) . ?
N1 H1 0.8800 . ?
N1 C8 1.274(16) . ?
N1 C9 1.439(14) . ?
N2 H2 1.0000 . ?
N2 C10 1.485(16) . ?
N2 C11 1.530(16) . ?
N2 C13 1.545(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.489(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.499(18) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.514(18) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
Zn1 Zn1 Zn1 107.970(14) 2_665 3_564 ?
O1 Zn1 Zn1 39.53(7) 3_564 3_564 ?
O1 Zn1 Zn1 39.84(7) . 2_665 ?
O1 Zn1 Zn1 121.39(7) . 3_564 ?
O1 Zn1 Zn1 133.79(8) 3_564 2_665 ?
O1 Zn1 O1 160.92(10) . 3_564 ?
O1 Zn1 O2 81.48(9) . . ?
O1 Zn1 O2 90.49(9) 3_564 2_665 ?
O1 Zn1 O2 80.49(8) 3_564 . ?
O1 Zn1 O2 80.02(9) . 2_665 ?
O1 Zn1 O3 98.51(10) . 3_565 ?
O1 Zn1 N3 97.1(6) . . ?
O1 Zn1 N3 90.6(6) 3_564 . ?
O1 Zn1 O4 91.0(5) . . ?
O1 Zn1 O4 98.6(5) 3_564 . ?
O2 Zn1 Zn1 44.12(7) . 3_564 ?
O2 Zn1 Zn1 89.82(6) . 2_665 ?
O2 Zn1 Zn1 71.34(6) 2_665 3_564 ?
O2 Zn1 Zn1 43.32(6) 2_665 2_665 ?
O2 Zn1 O2 79.22(2) . 2_665 ?
O3 Zn1 Zn1 83.97(6) 3_565 2_665 ?
O3 Zn1 Zn1 130.97(7) 3_565 3_564 ?
O3 Zn1 O1 98.15(9) 3_565 3_564 ?
O3 Zn1 O2 90.89(9) 3_565 2_665 ?
O3 Zn1 O2 169.98(10) 3_565 . ?
O3 Zn1 N3 95.1(6) 3_565 . ?
O3 Zn1 O4 88.4(5) 3_565 . ?
N3 Zn1 Zn1 105.9(5) . 3_564 ?
N3 Zn1 Zn1 135.4(6) . 2_665 ?
N3 Zn1 O2 173.7(7) . 2_665 ?
N3 Zn1 O2 94.8(6) . . ?
O4 Zn1 Zn1 115.7(4) . 3_564 ?
O4 Zn1 Zn1 127.6(5) . 2_665 ?
O4 Zn1 O2 170.8(5) . 2_665 ?
O4 Zn1 O2 101.6(5) . . ?
Zn1 O1 Zn1 100.62(11) . 2_665 ?
C1 O1 Zn1 124.9(2) . 2_665 ?
C1 O1 Zn1 123.02(18) . . ?
Zn1 O2 Zn1 92.56(9) . 3_564 ?
C7 O2 Zn1 123.8(2) . . ?
C7 O2 Zn1 135.8(2) . 3_564 ?
C7 O3 Zn1 124.7(2) . 2_664 ?
O1 C1 C2 124.4(3) . . ?
O1 C1 C6 117.9(3) . . ?
C6 C1 C2 117.6(3) . . ?
C1 C2 C7 123.8(3) . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 C7 117.6(3) . . ?
C2 C3 H3 118.2 . . ?
C4 C3 C2 123.7(3) . . ?
C4 C3 H3 118.2 . . ?
C3 C4 C4 121.8(3) . 4_556 ?
C3 C4 C5 117.0(3) . . ?
C5 C4 C4 121.2(4) . 4_556 ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 119.0 . . ?
C5 C6 C1 122.0(3) . . ?
C5 C6 H6 119.0 . . ?
O2 C7 O3 123.4(3) . . ?
O2 C7 C2 119.0(3) . . ?
O3 C7 C2 117.6(3) . . ?
Zn1 N3 H3A 108.4 . . ?
Zn1 N3 H3B 108.4 . . ?
H3A N3 H3B 107.4 . . ?
C15 N3 Zn1 115.6(12) . . ?
C15 N3 H3A 108.4 . . ?
C15 N3 H3B 108.4 . . ?
C16 N4 C17 107.9(15) . . ?
C16 N4 C19 110.4(15) . . ?
C17 N4 C19 117.2(18) . . ?
N3 C15 H15A 109.6 . . ?
N3 C15 H15B 109.6 . . ?
N3 C15 C16 110.4(11) . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
N4 C16 C15 106.5(10) . . ?
N4 C16 H16A 110.4 . . ?
N4 C16 H16B 110.4 . . ?
C15 C16 H16A 110.4 . . ?
C15 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
N4 C17 H17A 108.9 . . ?
N4 C17 H17B 108.9 . . ?
N4 C17 C18 113(2) . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18E 109.5 . . ?
C17 C18 H18D 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
C17 C18 H18F 109.5 . . ?
H18A C18 H18E 109.5 . . ?
H18A C18 H18D 109.5 . . ?
H18A C18 H18B 141.1 . . ?
H18A C18 H18C 56.3 . . ?
H18A C18 H18F 56.3 . . ?
H18E C18 H18D 109.5 . . ?
H18E C18 H18B 56.3 . . ?
H18E C18 H18C 141.1 . . ?
H18E C18 H18F 56.3 . . ?
H18D C18 H18B 56.3 . . ?
H18D C18 H18C 56.3 . . ?
H18D C18 H18F 141.1 . . ?
H18B C18 H18C 109.5 . . ?
H18B C18 H18F 109.5 . . ?
H18C C18 H18F 109.5 . . ?
N4 C19 H19A 109.0 . . ?
N4 C19 H19B 109.0 . . ?
N4 C19 C20 113.0(16) . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
C19 C20 H20D 109.5 . . ?
C19 C20 H20E 109.5 . . ?
C19 C20 H20F 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20A C20 H20D 141.1 . . ?
H20A C20 H20E 56.3 . . ?
H20A C20 H20F 56.3 . . ?
H20B C20 H20C 109.5 . . ?
H20B C20 H20D 56.3 . . ?
H20B C20 H20E 141.1 . . ?
H20B C20 H20F 56.3 . . ?
H20C C20 H20D 56.3 . . ?
H20C C20 H20E 56.3 . . ?
H20C C20 H20F 141.1 . . ?
H20D C20 H20E 109.5 . . ?
H20D C20 H20F 109.5 . . ?
H20E C20 H20F 109.5 . . ?
C8 O4 Zn1 140.6(12) . . ?
C8 N1 H1 119.0 . . ?
C8 N1 C9 122.1(11) . . ?
C9 N1 H1 119.0 . . ?
C10 N2 H2 105.9 . . ?
C10 N2 C11 112.4(11) . . ?
C10 N2 C13 112.5(10) . . ?
C11 N2 H2 105.9 . . ?
C11 N2 C13 113.4(11) . . ?
C13 N2 H2 105.9 . . ?
O5 C8 O4 122.0(13) . . ?
N1 C8 O4 114.1(13) . . ?
N1 C8 O5 123.8(11) . . ?
N1 C9 H9A 109.6 . . ?
N1 C9 H9B 109.6 . . ?
N1 C9 C10 110.4(10) . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
N2 C10 C9 112.8(11) . . ?
N2 C10 H10A 109.0 . . ?
N2 C10 H10B 109.0 . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
N2 C11 H11A 108.7 . . ?
N2 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 N2 114.4(13) . . ?
C12 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 108.3 . . ?
N2 C13 H13B 108.3 . . ?
H13A C13 H13B 107.4 . . ?
C14 C13 N2 115.9(11) . . ?
C14 C13 H13A 108.3 . . ?
C14 C13 H13B 108.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
N1 H1 O2 0.88 2.59 3.346(10) 144.3 .
N1 H1 O2 0.88 2.16 2.929(11) 145.0 3_564

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
Zn1 O1 C1 C2 -106.6(3) 2_665 . . . ?
Zn1 O1 C1 C2 29.5(5) . . . . ?
Zn1 O1 C1 C6 -150.5(3) . . . . ?
Zn1 O1 C1 C6 73.3(4) 2_665 . . . ?
Zn1 O2 C7 O3 5.3(5) 3_564 . . . ?
Zn1 O2 C7 O3 145.2(3) . . . . ?
Zn1 O2 C7 C2 -177.1(2) 3_564 . . . ?
Zn1 O2 C7 C2 -37.3(4) . . . . ?
Zn1 O3 C7 O2 -11.6(5) 2_664 . . . ?
Zn1 O3 C7 C2 170.9(2) 2_664 . . . ?
Zn1 N3 C15 C16 170.4(12) . . . . ?
Zn1 O4 C8 O5 164.6(17) . . . . ?
Zn1 O4 C8 N1 -18(3) . . . . ?
O1 C1 C2 C3 -178.3(3) . . . . ?
O1 C1 C2 C7 4.2(6) . . . . ?
O1 C1 C6 C5 178.8(4) . . . . ?
C1 C2 C3 C4 -1.2(5) . . . . ?
C1 C2 C7 O2 0.8(5) . . . . ?
C1 C2 C7 O3 178.4(3) . . . . ?
C2 C1 C6 C5 -1.3(6) . . . . ?
C2 C3 C4 C4 -178.6(3) . . . 4_556 ?
C2 C3 C4 C5 0.2(6) . . . . ?
C3 C2 C7 O2 -176.7(3) . . . . ?
C3 C2 C7 O3 1.0(5) . . . . ?
C3 C4 C5 C6 0.4(6) . . . . ?
C4 C4 C5 C6 179.1(3) 4_556 . . . ?
C4 C5 C6 C1 0.2(6) . . . . ?
C6 C1 C2 C3 1.7(5) . . . . ?
C6 C1 C2 C7 -175.7(3) . . . . ?
C7 C2 C3 C4 176.4(3) . . . . ?
N3 C15 C16 N4 55.9(17) . . . . ?
C16 N4 C17 C18 -170.4(17) . . . . ?
C16 N4 C19 C20 67(3) . . . . ?
C17 N4 C16 C15 77.5(16) . . . . ?
C17 N4 C19 C20 -168(2) . . . . ?
C19 N4 C16 C15 -153.2(13) . . . . ?
C19 N4 C17 C18 64(3) . . . . ?
N1 C9 C10 N2 178.4(11) . . . . ?
C8 N1 C9 C10 69.1(17) . . . . ?
C9 N1 C8 O4 -173.9(15) . . . . ?
C9 N1 C8 O5 4(3) . . . . ?
C10 N2 C11 C12 57.0(18) . . . . ?
C10 N2 C13 C14 60.2(15) . . . . ?
C11 N2 C10 C9 53.6(15) . . . . ?
C11 N2 C13 C14 -170.8(12) . . . . ?
C13 N2 C10 C9 -176.9(11) . . . . ?
C13 N2 C11 C12 -72.0(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.505(18)
2 0.495(18)



_chemical_properties_physical    Moisture-sensitive
