# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_ada256
_database_code_depnum_ccdc_archive 'CCDC 2045786'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2020-11-22 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;
_audit_creation_date             2020-02-07
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H44 N4 O8 Zn, 2(C H2 Cl2)'
_chemical_formula_sum            'C46 H48 Cl4 N4 O8 Zn'
_chemical_formula_weight         992.05
_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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2596(5)
_cell_length_b                   9.9708(6)
_cell_length_c                   15.6266(9)
_cell_angle_alpha                96.284(4)
_cell_angle_beta                 99.271(4)
_cell_angle_gamma                110.636(4)
_cell_volume                     1169.21(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3417
_cell_measurement_temperature    100
_cell_measurement_theta_max      69.978
_cell_measurement_theta_min      2.913
_shelx_estimated_absorpt_T_max   0.809
_shelx_estimated_absorpt_T_min   0.693
_exptl_absorpt_coefficient_mu    3.296
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0831 before and 0.0453 after correction.
The Ratio of minimum to maximum transmission is 0.8698.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             514
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.067
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 180.0 degree
scan in 180 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10190
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.062
_diffrn_reflns_theta_min         2.913
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Microfocus Source'
_diffrn_source_current           0.65
_diffrn_source_power             0.02912
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_diffrn_source_voltage           44.8
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3727
_reflns_number_total             4192
_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 (2017) V8.38A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2017) V8.38A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.894
_refine_diff_density_min         -1.094
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         4192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0534
_refine_ls_restrained_S_all      1.065
_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)+(0.0679P)²+1.4452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1405
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1), N2(H2A)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,
 H22B), C1A(H1AA,H1AB)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C12(H12), C13(H13), C15(H15), C16(H16)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Zn1 Zn 1.000000 1.000000 1.000000 0.01961(16) Uani 1 2 d S . P . .
O1 O 0.5732(3) 0.8534(2) 0.16626(14) 0.0308(5) Uani 1 1 d . . . . .
O2 O 0.4327(3) 0.6248(2) 0.09106(13) 0.0267(4) Uani 1 1 d . . . . .
H2 H 0.486034 0.658355 0.053523 0.040 Uiso 1 1 calc R U . . .
O3 O 0.6139(2) 0.7128(2) 0.97518(12) 0.0231(4) Uani 1 1 d . . . . .
O4 O 0.7235(2) 0.9207(2) 0.92536(13) 0.0237(4) Uani 1 1 d . . . . .
N1 N 1.0752(3) 1.0332(3) 0.88042(16) 0.0310(6) Uani 1 1 d . . . . .
H1 H 1.203621 1.087642 0.894124 0.037 Uiso 1 1 calc R U . . .
N2 N 1.0090(3) 0.7913(3) 0.96988(18) 0.0312(6) Uani 1 1 d . . . . .
H2A H 0.887395 0.721520 0.946465 0.037 Uiso 1 1 calc R U . . .
C1 C 0.4697(4) 0.7288(3) 0.15935(18) 0.0229(6) Uani 1 1 d . . . . .
C2 C 0.3689(4) 0.6795(3) 0.22893(18) 0.0221(6) Uani 1 1 d . . . . .
C3 C 0.3631(4) 0.7825(3) 0.29448(18) 0.0249(6) Uani 1 1 d . . . . .
H3 H 0.425426 0.880942 0.295882 0.030 Uiso 1 1 calc R U . . .
C4 C 0.2655(4) 0.7402(3) 0.35770(18) 0.0244(6) Uani 1 1 d . . . . .
H4 H 0.261376 0.810474 0.400736 0.029 Uiso 1 1 calc R U . . .
C5 C 0.1725(3) 0.5920(3) 0.35736(18) 0.0227(6) Uani 1 1 d . . . . .
C6 C 0.1818(4) 0.4891(3) 0.29227(18) 0.0253(6) Uani 1 1 d . . . . .
H6 H 0.122634 0.390490 0.291858 0.030 Uiso 1 1 calc R U . . .
C7 C 0.2777(4) 0.5313(3) 0.22831(18) 0.0243(6) Uani 1 1 d . . . . .
H7 H 0.281463 0.461354 0.184977 0.029 Uiso 1 1 calc R U . . .
C8 C 0.0762(4) 0.5455(3) 0.42822(18) 0.0243(6) Uani 1 1 d . . . . .
C9 C 0.1677(4) 0.6033(3) 0.51519(18) 0.0253(6) Uani 1 1 d . . . . .
H9 H 0.281411 0.673964 0.525411 0.030 Uiso 1 1 calc R U . . .
C10 C 0.0973(4) 0.5606(3) 0.58791(18) 0.0239(6) Uani 1 1 d . . . . .
C11 C 0.2161(4) 0.6209(3) 0.67679(18) 0.0229(6) Uani 1 1 d . . . . .
C12 C 0.2369(4) 0.5304(3) 0.73619(18) 0.0232(6) Uani 1 1 d . . . . .
H12 H 0.167329 0.431418 0.722545 0.028 Uiso 1 1 calc R U . . .
C13 C 0.3603(4) 0.5865(3) 0.81539(18) 0.0219(6) Uani 1 1 d . . . . .
H13 H 0.371805 0.525114 0.854663 0.026 Uiso 1 1 calc R U . . .
C14 C 0.4672(3) 0.7342(3) 0.83650(17) 0.0200(5) Uani 1 1 d . . . . .
C15 C 0.4453(4) 0.8256(3) 0.77805(18) 0.0220(6) Uani 1 1 d . . . . .
H15 H 0.514771 0.924669 0.791890 0.026 Uiso 1 1 calc R U . . .
C16 C 0.3204(4) 0.7697(3) 0.69944(18) 0.0238(6) Uani 1 1 d . . . . .
H16 H 0.305822 0.831929 0.661291 0.029 Uiso 1 1 calc R U . . .
C17 C 0.6104(3) 0.7947(3) 0.91961(17) 0.0204(5) Uani 1 1 d . . . . .
C18 C 0.9932(4) 1.1195(4) 0.8287(2) 0.0425(9) Uani 1 1 d . . . . .
H18A H 0.867415 1.062921 0.807865 0.051 Uiso 1 1 calc R U . . .
H18B H 1.045014 1.136673 0.777568 0.051 Uiso 1 1 calc R U . . .
C19 C 1.0434(4) 0.8889(4) 0.8331(2) 0.0403(8) Uani 1 1 d . . . . .
H19A H 1.107417 0.897699 0.785783 0.048 Uiso 1 1 calc R U . . .
H19B H 0.918046 0.838226 0.807394 0.048 Uiso 1 1 calc R U . . .
C20 C 1.1051(4) 0.8038(4) 0.8968(2) 0.0415(9) Uani 1 1 d . . . . .
H20A H 1.083723 0.707277 0.865953 0.050 Uiso 1 1 calc R U . . .
H20B H 1.231431 0.852804 0.920567 0.050 Uiso 1 1 calc R U . . .
C21 C 1.0853(4) 0.7414(4) 1.0453(3) 0.0413(9) Uani 1 1 d . . . . .
H21A H 1.207457 0.806925 1.068186 0.050 Uiso 1 1 calc R U . . .
H21B H 1.084318 0.645193 1.026178 0.050 Uiso 1 1 calc R U . . .
C22 C 0.9819(5) 0.7357(4) 1.1183(3) 0.0463(10) Uani 1 1 d . . . . .
H22A H 0.856912 0.685038 1.091932 0.056 Uiso 1 1 calc R U . . .
H22B H 1.015115 0.677765 1.158603 0.056 Uiso 1 1 calc R U . . .
Cl1A Cl 0.1685(2) 0.15513(18) 0.59105(10) 0.0930(5) Uani 1 1 d . . . . .
Cl2A Cl 0.3195(2) 0.2334(3) 0.43961(10) 0.1506(11) Uani 1 1 d . . . . .
C1A C 0.3028(8) 0.2914(7) 0.5462(4) 0.0855(18) Uani 1 1 d . . . . .
H1AA H 0.420331 0.332056 0.583978 0.103 Uiso 1 1 calc R U . . .
H1AB H 0.256840 0.368469 0.545150 0.103 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
Zn1 O4 2.2061(19) . ?
Zn1 O4 2.2061(19) 2_777 ?
Zn1 N1 2.086(2) . ?
Zn1 N1 2.086(2) 2_777 ?
Zn1 N2 2.112(2) . ?
Zn1 N2 2.112(2) 2_777 ?
O1 C1 1.216(3) . ?
O2 H2 0.8200 . ?
O2 C1 1.318(3) . ?
O3 C17 1.259(3) . ?
O4 C17 1.257(3) . ?
N1 H1 0.9800 . ?
N1 C18 1.496(4) . ?
N1 C19 1.457(5) . ?
N2 H2A 0.9800 . ?
N2 C20 1.484(4) . ?
N2 C21 1.465(4) . ?
C1 C2 1.496(4) . ?
C2 C3 1.388(4) . ?
C2 C7 1.400(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.404(4) . ?
C5 C6 1.395(4) . ?
C5 C8 1.487(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.384(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(4) . ?
C8 C10 1.412(4) 2_566 ?
C9 H9 0.9300 . ?
C9 C10 1.398(4) . ?
C10 C11 1.488(4) . ?
C11 C12 1.395(4) . ?
C11 C16 1.399(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.387(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.393(4) . ?
C14 C15 1.394(4) . ?
C14 C17 1.510(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(4) . ?
C16 H16 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C22 1.512(6) 2_777 ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.517(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.525(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
Cl1A C1A 1.721(6) . ?
Cl2A C1A 1.746(6) . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?

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 Zn1 O4 180.0 2_777 . ?
N1 Zn1 O4 86.91(9) 2_777 2_777 ?
N1 Zn1 O4 86.91(8) . . ?
N1 Zn1 O4 93.09(9) . 2_777 ?
N1 Zn1 O4 93.09(9) 2_777 . ?
N1 Zn1 N1 180.0 . 2_777 ?
N1 Zn1 N2 94.48(11) 2_777 . ?
N1 Zn1 N2 85.52(11) 2_777 2_777 ?
N1 Zn1 N2 94.48(11) . 2_777 ?
N1 Zn1 N2 85.52(11) . . ?
N2 Zn1 O4 91.16(9) . . ?
N2 Zn1 O4 88.84(9) . 2_777 ?
N2 Zn1 O4 91.16(9) 2_777 2_777 ?
N2 Zn1 O4 88.84(9) 2_777 . ?
N2 Zn1 N2 180.00(15) . 2_777 ?
C1 O2 H2 109.5 . . ?
C17 O4 Zn1 124.82(18) . . ?
Zn1 N1 H1 107.0 . . ?
C18 N1 Zn1 115.5(2) . . ?
C18 N1 H1 107.0 . . ?
C19 N1 Zn1 105.6(2) . . ?
C19 N1 H1 107.0 . . ?
C19 N1 C18 114.3(3) . . ?
Zn1 N2 H2A 107.9 . . ?
C20 N2 Zn1 103.6(2) . . ?
C20 N2 H2A 107.9 . . ?
C21 N2 Zn1 114.4(2) . . ?
C21 N2 H2A 107.9 . . ?
C21 N2 C20 114.7(3) . . ?
O1 C1 O2 124.6(3) . . ?
O1 C1 C2 122.2(3) . . ?
O2 C1 C2 113.2(2) . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 C7 119.3(3) . . ?
C7 C2 C1 121.2(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C8 120.7(3) . . ?
C6 C5 C4 118.5(3) . . ?
C6 C5 C8 120.7(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.1(3) . . ?
C7 C6 H6 119.4 . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 119.9(3) . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C5 117.6(2) . . ?
C9 C8 C10 118.7(3) . 2_566 ?
C10 C8 C5 123.5(2) 2_566 . ?
C8 C9 H9 118.3 . . ?
C8 C9 C10 123.4(3) . . ?
C10 C9 H9 118.3 . . ?
C8 C10 C11 124.3(3) 2_566 . ?
C9 C10 C8 117.9(3) . 2_566 ?
C9 C10 C11 117.5(2) . . ?
C12 C11 C10 121.4(3) . . ?
C12 C11 C16 118.5(3) . . ?
C16 C11 C10 119.8(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C15 119.1(2) . . ?
C13 C14 C17 120.9(2) . . ?
C15 C14 C17 119.9(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
O3 C17 C14 118.0(2) . . ?
O4 C17 O3 125.0(2) . . ?
O4 C17 C14 116.9(2) . . ?
N1 C18 H18A 109.0 . . ?
N1 C18 H18B 109.0 . . ?
N1 C18 C22 113.0(3) . 2_777 ?
H18A C18 H18B 107.8 . . ?
C22 C18 H18A 109.0 2_777 . ?
C22 C18 H18B 109.0 2_777 . ?
N1 C19 H19A 109.9 . . ?
N1 C19 H19B 109.9 . . ?
N1 C19 C20 109.0(3) . . ?
H19A C19 H19B 108.3 . . ?
C20 C19 H19A 109.9 . . ?
C20 C19 H19B 109.9 . . ?
N2 C20 C19 110.2(3) . . ?
N2 C20 H20A 109.6 . . ?
N2 C20 H20B 109.6 . . ?
C19 C20 H20A 109.6 . . ?
C19 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?
N2 C21 H21A 109.4 . . ?
N2 C21 H21B 109.4 . . ?
N2 C21 C22 111.4(3) . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
C18 C22 C21 116.4(3) 2_777 . ?
C18 C22 H22A 108.2 2_777 . ?
C18 C22 H22B 108.2 2_777 . ?
C21 C22 H22A 108.2 . . ?
C21 C22 H22B 108.2 . . ?
H22A C22 H22B 107.3 . . ?
Cl1A C1A Cl2A 113.8(4) . . ?
Cl1A C1A H1AA 108.8 . . ?
Cl1A C1A H1AB 108.8 . . ?
Cl2A C1A H1AA 108.8 . . ?
Cl2A C1A H1AB 108.8 . . ?
H1AA C1A H1AB 107.7 . . ?

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 O4 C17 O3 24.9(4) . . . . ?
Zn1 O4 C17 C14 -150.73(18) . . . . ?
Zn1 N1 C18 C22 53.3(3) . . . 2_777 ?
Zn1 N1 C19 C20 -42.3(3) . . . . ?
Zn1 N2 C20 C19 -41.1(3) . . . . ?
Zn1 N2 C21 C22 58.9(3) . . . . ?
O1 C1 C2 C3 13.7(4) . . . . ?
O1 C1 C2 C7 -167.5(3) . . . . ?
O2 C1 C2 C3 -165.5(2) . . . . ?
O2 C1 C2 C7 13.3(4) . . . . ?
N1 C19 C20 N2 58.9(3) . . . . ?
N2 C21 C22 C18 -73.6(4) . . . 2_777 ?
C1 C2 C3 C4 177.6(3) . . . . ?
C1 C2 C7 C6 -178.3(3) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C3 C2 C7 C6 0.5(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C3 C4 C5 C8 176.3(3) . . . . ?
C4 C5 C6 C7 -1.1(4) . . . . ?
C4 C5 C8 C9 -49.7(4) . . . . ?
C4 C5 C8 C10 134.7(3) . . . 2_566 ?
C5 C6 C7 C2 0.7(4) . . . . ?
C5 C8 C9 C10 -175.1(3) . . . . ?
C6 C5 C8 C9 126.2(3) . . . . ?
C6 C5 C8 C10 -49.4(4) . . . 2_566 ?
C7 C2 C3 C4 -1.3(4) . . . . ?
C8 C5 C6 C7 -177.1(3) . . . . ?
C8 C9 C10 C8 -0.7(5) . . . 2_566 ?
C8 C9 C10 C11 174.2(3) . . . . ?
C8 C10 C11 C12 45.9(4) 2_566 . . . ?
C8 C10 C11 C16 -139.2(3) 2_566 . . . ?
C9 C10 C11 C12 -128.6(3) . . . . ?
C9 C10 C11 C16 46.3(4) . . . . ?
C10 C8 C9 C10 0.7(5) 2_566 . . . ?
C10 C11 C12 C13 173.9(3) . . . . ?
C10 C11 C16 C15 -173.2(3) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C12 C11 C16 C15 1.8(4) . . . . ?
C12 C13 C14 C15 1.7(4) . . . . ?
C12 C13 C14 C17 -175.8(2) . . . . ?
C13 C14 C15 C16 -0.9(4) . . . . ?
C13 C14 C17 O3 -10.0(4) . . . . ?
C13 C14 C17 O4 165.9(2) . . . . ?
C14 C15 C16 C11 -0.8(4) . . . . ?
C15 C14 C17 O3 172.5(2) . . . . ?
C15 C14 C17 O4 -11.6(4) . . . . ?
C16 C11 C12 C13 -1.0(4) . . . . ?
C17 C14 C15 C16 176.6(2) . . . . ?
C18 N1 C19 C20 -170.3(3) . . . . ?
C19 N1 C18 C22 176.1(3) . . . 2_777 ?
C20 N2 C21 C22 178.4(3) . . . . ?
C21 N2 C20 C19 -166.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ada255
_database_code_depnum_ccdc_archive 'CCDC 2045790'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2020-11-22 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;
_audit_creation_date             2020-07-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H44 Cu N4 O8, 2(C H2 Cl2)'
_chemical_formula_sum            'C46 H48 Cl4 Cu N4 O8'
_chemical_formula_weight         990.22
_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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0935(8)
_cell_length_b                   10.0336(9)
_cell_length_c                   15.6580(12)
_cell_angle_alpha                96.030(5)
_cell_angle_beta                 98.336(5)
_cell_angle_gamma                109.647(5)
_cell_volume                     1168.61(18)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1445
_cell_measurement_temperature    100
_cell_measurement_theta_max      63.675
_cell_measurement_theta_min      2.892
_shelx_estimated_absorpt_T_max   0.698
_shelx_estimated_absorpt_T_min   0.594
_exptl_absorpt_coefficient_mu    3.228
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0723 before and 0.0438 after correction.
The Ratio of minimum to maximum transmission is 0.6713.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light purple'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    purple
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             513
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 180.0 degree
scan in 180 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.947
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8138
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.027
_diffrn_reflns_theta_min         2.892
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3367
_reflns_number_total             4163
_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 (2017) V8.38A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2017) V8.38A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0611
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0959P)²+0.6128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1687
_refine_ls_wR_factor_ref         0.1794
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Sof(H1AC)=Sof(H1AD)=Sof(Cl1B)=Sof(Cl2B)=1-FVAR(1)
 Sof(H1AA)=Sof(H1AB)=Sof(Cl1A)=Sof(Cl2A)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 N1(H1A), N2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,
 H22B), C1A(H1AA,H1AB), C1A(H1AC,H1AD)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C12(H12), C13(H13), C15(H15), C16(H16)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 1.000000 1.000000 1.000000 0.0424(2) Uani 1 2 d S . P . .
O1 O 0.4423(3) 0.6338(3) 0.08960(15) 0.0493(6) Uani 1 1 d . . . . .
H1 H 0.490924 0.669611 0.050815 0.074 Uiso 1 1 calc R U . . .
O2 O 0.5869(3) 0.8543(3) 0.16691(15) 0.0511(6) Uani 1 1 d . . . . .
O3 O 0.6131(3) 0.7075(2) 0.96773(14) 0.0455(5) Uani 1 1 d . . . . .
O4 O 0.6906(3) 0.9252(3) 0.92887(15) 0.0480(6) Uani 1 1 d . . . . .
N1 N 1.0027(4) 0.7981(3) 0.9807(2) 0.0505(7) Uani 1 1 d . . . . .
H1A H 0.878280 0.733175 0.960962 0.061 Uiso 1 1 calc R U . . .
N2 N 1.0673(4) 1.0162(4) 0.88149(18) 0.0526(7) Uani 1 1 d . . . . .
H2 H 1.197124 1.066175 0.891991 0.063 Uiso 1 1 calc R U . . .
C1 C 0.4799(5) 0.7338(4) 0.1589(2) 0.0441(7) Uani 1 1 d . . . . .
C2 C 0.3745(4) 0.6830(4) 0.2270(2) 0.0434(7) Uani 1 1 d . . . . .
C3 C 0.2792(5) 0.5384(4) 0.2247(2) 0.0476(8) Uani 1 1 d . . . . .
H3 H 0.281115 0.470749 0.179824 0.057 Uiso 1 1 calc R U . . .
C4 C 0.1812(5) 0.4940(4) 0.2888(2) 0.0478(8) Uani 1 1 d . . . . .
H4 H 0.119743 0.396713 0.286995 0.057 Uiso 1 1 calc R U . . .
C5 C 0.1737(5) 0.5941(4) 0.3562(2) 0.0450(8) Uani 1 1 d . . . . .
C6 C 0.2702(5) 0.7392(4) 0.3579(2) 0.0464(8) Uani 1 1 d . . . . .
H6 H 0.267304 0.807351 0.402243 0.056 Uiso 1 1 calc R U . . .
C7 C 0.3696(5) 0.7829(4) 0.2947(2) 0.0457(8) Uani 1 1 d . . . . .
H7 H 0.433999 0.879845 0.297284 0.055 Uiso 1 1 calc R U . . .
C8 C 0.0767(5) 0.5462(4) 0.4277(2) 0.0461(8) Uani 1 1 d . . . . .
C9 C 0.1671(5) 0.6015(4) 0.5137(2) 0.0477(8) Uani 1 1 d . . . . .
H9 H 0.280890 0.671202 0.522973 0.057 Uiso 1 1 calc R U . . .
C10 C 0.0968(5) 0.5582(4) 0.5864(2) 0.0467(8) Uani 1 1 d . . . . .
C11 C 0.2154(5) 0.6193(4) 0.6741(2) 0.0457(8) Uani 1 1 d . . . . .
C12 C 0.3118(5) 0.7662(4) 0.6962(2) 0.0451(8) Uani 1 1 d . . . . .
H12 H 0.294696 0.827094 0.657714 0.054 Uiso 1 1 calc R U . . .
C13 C 0.4327(4) 0.8227(4) 0.7745(2) 0.0435(7) Uani 1 1 d . . . . .
H13 H 0.496158 0.920952 0.788077 0.052 Uiso 1 1 calc R U . . .
C14 C 0.4597(4) 0.7336(4) 0.83279(19) 0.0418(7) Uani 1 1 d . . . . .
C15 C 0.3625(5) 0.5877(4) 0.8121(2) 0.0444(7) Uani 1 1 d . . . . .
H15 H 0.378428 0.527262 0.851160 0.053 Uiso 1 1 calc R U . . .
C16 C 0.2416(5) 0.5311(4) 0.7335(2) 0.0469(8) Uani 1 1 d . . . . .
H16 H 0.177188 0.432920 0.720377 0.056 Uiso 1 1 calc R U . . .
C17 C 0.5978(4) 0.7960(4) 0.9170(2) 0.0435(7) Uani 1 1 d . . . . .
C18 C 1.0320(6) 0.8691(5) 0.8389(3) 0.0652(11) Uani 1 1 d . . . . .
H18A H 1.095462 0.870859 0.790737 0.078 Uiso 1 1 calc R U . . .
H18B H 0.905148 0.820745 0.815853 0.078 Uiso 1 1 calc R U . . .
C19 C 1.0949(5) 0.7909(5) 0.9063(3) 0.0654(11) Uani 1 1 d . . . . .
H19A H 1.067243 0.691579 0.880935 0.078 Uiso 1 1 calc R U . . .
H19B H 1.223321 0.835165 0.926201 0.078 Uiso 1 1 calc R U . . .
C20 C 1.0783(5) 0.7469(4) 1.0564(3) 0.0659(11) Uani 1 1 d . . . . .
H20A H 1.203900 0.805316 1.075709 0.079 Uiso 1 1 calc R U . . .
H20B H 1.069275 0.648631 1.039138 0.079 Uiso 1 1 calc R U . . .
C21 C 0.9800(6) 0.7545(5) 1.1314(3) 0.0724(13) Uani 1 1 d . . . . .
H21A H 0.852750 0.706767 1.109216 0.087 Uiso 1 1 calc R U . . .
H21B H 1.015327 0.701850 1.174734 0.087 Uiso 1 1 calc R U . . .
C22 C 0.9872(6) 1.0960(5) 0.8241(3) 0.0685(12) Uani 1 1 d . . . . .
H22A H 0.859381 1.044079 0.806992 0.082 Uiso 1 1 calc R U . . .
H22B H 1.037383 1.101325 0.771396 0.082 Uiso 1 1 calc R U . . .
C1A C 0.2766(12) 0.2732(10) 0.5369(5) 0.143(3) Uani 1 1 d . . . . .
H1AA H 0.393468 0.326245 0.573082 0.172 Uiso 0.805(7) 1 calc R U P A 1
H1AB H 0.216084 0.340564 0.527811 0.172 Uiso 0.805(7) 1 calc R U P A 1
H1AC H 0.178992 0.308089 0.539362 0.172 Uiso 0.195(7) 1 calc R U P A 2
H1AD H 0.373693 0.331286 0.584395 0.172 Uiso 0.195(7) 1 calc R U P A 2
Cl1A Cl 0.1619(3) 0.1525(3) 0.59073(13) 0.1034(9) Uani 0.805(7) 1 d . . P A 1
Cl2A Cl 0.3062(3) 0.2018(5) 0.43389(15) 0.1318(14) Uani 0.805(7) 1 d . . P A 1
Cl1B Cl 0.199(3) 0.082(3) 0.5608(16) 0.234(10) Uiso 0.195(7) 1 d . . P A 2
Cl2B Cl 0.3463(13) 0.3052(12) 0.4427(6) 0.095(3) Uiso 0.195(7) 1 d . . P A 2


_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 O4 2.414(2) . ?
Cu1 O4 2.414(2) 2_777 ?
Cu1 N1 2.024(3) . ?
Cu1 N1 2.024(3) 2_777 ?
Cu1 N2 2.016(3) . ?
Cu1 N2 2.016(3) 2_777 ?
O1 H1 0.8200 . ?
O1 C1 1.322(4) . ?
O2 C1 1.208(4) . ?
O3 C17 1.276(4) . ?
O4 C17 1.238(4) . ?
N1 H1A 0.9800 . ?
N1 C19 1.480(5) . ?
N1 C20 1.474(5) . ?
N2 H2 0.9800 . ?
N2 C18 1.470(5) . ?
N2 C22 1.484(5) . ?
C1 C2 1.486(4) . ?
C2 C3 1.389(5) . ?
C2 C7 1.395(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.402(5) . ?
C5 C6 1.397(5) . ?
C5 C8 1.487(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.380(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(4) . ?
C8 C10 1.411(5) 2_566 ?
C9 H9 0.9300 . ?
C9 C10 1.391(5) . ?
C10 C11 1.492(4) . ?
C11 C12 1.394(5) . ?
C11 C16 1.391(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.388(5) . ?
C14 C15 1.385(5) . ?
C14 C17 1.519(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.388(5) . ?
C16 H16 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.509(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.521(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.505(7) 2_777 ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C1A H1AC 0.9700 . ?
C1A H1AD 0.9700 . ?
C1A Cl1A 1.650(8) . ?
C1A Cl2A 1.777(8) . ?
C1A Cl1B 1.90(2) . ?
C1A Cl2B 1.678(11) . ?

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 Cu1 O4 180.0 2_777 . ?
N1 Cu1 O4 93.10(10) . . ?
N1 Cu1 O4 93.10(10) 2_777 2_777 ?
N1 Cu1 O4 86.90(10) 2_777 . ?
N1 Cu1 O4 86.90(10) . 2_777 ?
N1 Cu1 N1 180.0 2_777 . ?
N2 Cu1 O4 91.67(10) . 2_777 ?
N2 Cu1 O4 88.33(10) . . ?
N2 Cu1 O4 88.33(10) 2_777 2_777 ?
N2 Cu1 O4 91.67(10) 2_777 . ?
N2 Cu1 N1 93.57(13) . 2_777 ?
N2 Cu1 N1 86.43(13) 2_777 2_777 ?
N2 Cu1 N1 93.57(13) 2_777 . ?
N2 Cu1 N1 86.43(13) . . ?
N2 Cu1 N2 180.0(2) . 2_777 ?
C1 O1 H1 109.5 . . ?
C17 O4 Cu1 118.5(2) . . ?
Cu1 N1 H1A 107.0 . . ?
C19 N1 Cu1 105.7(2) . . ?
C19 N1 H1A 107.0 . . ?
C20 N1 Cu1 117.4(2) . . ?
C20 N1 H1A 107.0 . . ?
C20 N1 C19 112.1(3) . . ?
Cu1 N2 H2 106.6 . . ?
C18 N2 Cu1 106.2(2) . . ?
C18 N2 H2 106.6 . . ?
C18 N2 C22 112.2(3) . . ?
C22 N2 Cu1 117.9(3) . . ?
C22 N2 H2 106.6 . . ?
O1 C1 C2 112.7(3) . . ?
O2 C1 O1 124.4(3) . . ?
O2 C1 C2 122.8(3) . . ?
C3 C2 C1 121.8(3) . . ?
C3 C2 C7 118.9(3) . . ?
C7 C2 C1 119.3(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.7(3) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C8 120.8(3) . . ?
C6 C5 C4 118.2(3) . . ?
C6 C5 C8 120.8(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.9(3) . . ?
C7 C6 H6 119.6 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.7(3) . . ?
C6 C7 H7 119.7 . . ?
C9 C8 C5 117.8(3) . . ?
C9 C8 C10 118.1(3) . 2_566 ?
C10 C8 C5 123.9(3) 2_566 . ?
C8 C9 H9 118.2 . . ?
C10 C9 C8 123.7(3) . . ?
C10 C9 H9 118.2 . . ?
C8 C10 C11 124.4(3) 2_566 . ?
C9 C10 C8 118.2(3) . 2_566 ?
C9 C10 C11 117.3(3) . . ?
C12 C11 C10 120.4(3) . . ?
C16 C11 C10 121.2(3) . . ?
C16 C11 C12 118.3(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C17 119.9(3) . . ?
C15 C14 C13 119.2(3) . . ?
C15 C14 C17 120.9(3) . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
O3 C17 C14 116.2(3) . . ?
O4 C17 O3 125.6(3) . . ?
O4 C17 C14 118.1(3) . . ?
N2 C18 H18A 110.1 . . ?
N2 C18 H18B 110.1 . . ?
N2 C18 C19 108.1(3) . . ?
H18A C18 H18B 108.4 . . ?
C19 C18 H18A 110.1 . . ?
C19 C18 H18B 110.1 . . ?
N1 C19 C18 108.2(3) . . ?
N1 C19 H19A 110.0 . . ?
N1 C19 H19B 110.0 . . ?
C18 C19 H19A 110.0 . . ?
C18 C19 H19B 110.0 . . ?
H19A C19 H19B 108.4 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
N1 C20 C21 110.9(3) . . ?
H20A C20 H20B 108.0 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C20 C21 H21A 108.6 . . ?
C20 C21 H21B 108.6 . . ?
H21A C21 H21B 107.5 . . ?
C22 C21 C20 114.8(3) 2_777 . ?
C22 C21 H21A 108.6 2_777 . ?
C22 C21 H21B 108.6 2_777 . ?
N2 C22 C21 112.2(3) . 2_777 ?
N2 C22 H22A 109.2 . . ?
N2 C22 H22B 109.2 . . ?
C21 C22 H22A 109.2 2_777 . ?
C21 C22 H22B 109.2 2_777 . ?
H22A C22 H22B 107.9 . . ?
H1AA C1A H1AB 107.5 . . ?
H1AC C1A H1AD 107.0 . . ?
Cl1A C1A H1AA 108.6 . . ?
Cl1A C1A H1AB 108.6 . . ?
Cl1A C1A Cl2A 114.8(6) . . ?
Cl2A C1A H1AA 108.6 . . ?
Cl2A C1A H1AB 108.6 . . ?
Cl1B C1A H1AC 107.5 . . ?
Cl1B C1A H1AD 107.5 . . ?
Cl2B C1A H1AC 107.5 . . ?
Cl2B C1A H1AD 107.5 . . ?
Cl2B C1A Cl1B 119.4(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 O4 C17 O3 33.6(4) . . . . ?
Cu1 O4 C17 C14 -142.9(2) . . . . ?
Cu1 N1 C19 C18 -40.8(3) . . . . ?
Cu1 N1 C20 C21 57.7(4) . . . . ?
Cu1 N2 C18 C19 -41.7(4) . . . . ?
Cu1 N2 C22 C21 54.8(4) . . . 2_777 ?
O1 C1 C2 C3 13.3(5) . . . . ?
O1 C1 C2 C7 -166.1(3) . . . . ?
O2 C1 C2 C3 -167.2(3) . . . . ?
O2 C1 C2 C7 13.4(5) . . . . ?
N1 C20 C21 C22 -70.3(5) . . . 2_777 ?
N2 C18 C19 N1 56.5(4) . . . . ?
C1 C2 C3 C4 -179.6(3) . . . . ?
C1 C2 C7 C6 178.7(3) . . . . ?
C2 C3 C4 C5 1.1(6) . . . . ?
C3 C2 C7 C6 -0.7(5) . . . . ?
C3 C4 C5 C6 -1.2(5) . . . . ?
C3 C4 C5 C8 -176.7(3) . . . . ?
C4 C5 C6 C7 0.2(5) . . . . ?
C4 C5 C8 C9 128.7(4) . . . . ?
C4 C5 C8 C10 -47.1(5) . . . 2_566 ?
C5 C6 C7 C2 0.7(5) . . . . ?
C5 C8 C9 C10 -175.3(3) . . . . ?
C6 C5 C8 C9 -46.7(5) . . . . ?
C6 C5 C8 C10 137.5(4) . . . 2_566 ?
C7 C2 C3 C4 -0.2(5) . . . . ?
C8 C5 C6 C7 175.8(3) . . . . ?
C8 C9 C10 C8 -0.8(6) . . . 2_566 ?
C8 C9 C10 C11 175.5(3) . . . . ?
C8 C10 C11 C12 -136.6(4) 2_566 . . . ?
C8 C10 C11 C16 47.6(5) 2_566 . . . ?
C9 C10 C11 C12 47.4(5) . . . . ?
C9 C10 C11 C16 -128.5(4) . . . . ?
C10 C8 C9 C10 0.8(6) 2_566 . . . ?
C10 C11 C12 C13 -174.9(3) . . . . ?
C10 C11 C16 C15 175.0(3) . . . . ?
C11 C12 C13 C14 -0.2(5) . . . . ?
C12 C11 C16 C15 -0.9(5) . . . . ?
C12 C13 C14 C15 -0.8(5) . . . . ?
C12 C13 C14 C17 177.7(3) . . . . ?
C13 C14 C15 C16 0.9(5) . . . . ?
C13 C14 C17 O3 179.1(3) . . . . ?
C13 C14 C17 O4 -4.0(5) . . . . ?
C14 C15 C16 C11 0.0(5) . . . . ?
C15 C14 C17 O3 -2.5(5) . . . . ?
C15 C14 C17 O4 174.4(3) . . . . ?
C16 C11 C12 C13 1.0(5) . . . . ?
C17 C14 C15 C16 -177.5(3) . . . . ?
C18 N2 C22 C21 178.7(3) . . . 2_777 ?
C19 N1 C20 C21 -179.5(3) . . . . ?
C20 N1 C19 C18 -170.0(3) . . . . ?
C22 N2 C18 C19 -171.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ada220
_database_code_depnum_ccdc_archive 'CCDC 2045788'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2020-11-22 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;
_audit_creation_date             2019-09-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H44 N4 O8 Zn, 2(C3 H7 N O)'
_chemical_formula_sum            'C50 H58 N6 O10 Zn'
_chemical_formula_weight         968.39
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1297(17)
_cell_length_b                   10.1868(19)
_cell_length_c                   15.619(3)
_cell_angle_alpha                94.957(13)
_cell_angle_beta                 99.778(13)
_cell_angle_gamma                110.086(13)
_cell_volume                     1182.4(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5918
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.433
_cell_measurement_theta_min      2.906
_shelx_estimated_absorpt_T_max   0.906
_shelx_estimated_absorpt_T_min   0.863
_exptl_absorpt_coefficient_mu    1.260
_exptl_absorpt_correction_T_max  0.1851
_exptl_absorpt_correction_T_min  0.0664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1369 before and 0.0684 after correction. The Ratio of minimum to maximum transmission is 0.3587. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             510
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 180.0 degree
scan in 180 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12885
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.446
_diffrn_reflns_theta_min         2.907
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Microfocus Source'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3686
_reflns_number_total             4166
_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 (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.732
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.053
_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)+(0.1093P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1387
_refine_ls_wR_factor_ref         0.1445
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1), N2(H2A)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C12(H12), C13(H13), C15(H15),
 C16(H16), C1A(H1A)
2.d Idealised Me refined as rotating group:
 C2A(H2AA,H2AB,H2AC), C3A(H3AA,H3AB,H3AC)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Zn1 Zn 0.000000 0.500000 0.000000 0.03145(16) Uani 1 2 d S T P . .
O1 O 0.4201(2) 0.65511(18) 0.83353(11) 0.0437(4) Uani 1 1 d . . . . .
O2 O 0.5639(2) 0.87280(17) 0.91148(10) 0.0380(3) Uani 1 1 d . . . . .
H2 H 0.501281 0.838842 0.947522 0.057 Uiso 1 1 calc GR . . . .
O3 O 0.37778(19) 0.78332(16) 0.02541(9) 0.0357(3) Uani 1 1 d . . . . .
O4 O 0.2790(2) 0.57843(16) 0.07568(10) 0.0358(3) Uani 1 1 d . . . . .
N1 N -0.0123(2) 0.70372(19) 0.01690(13) 0.0374(4) Uani 1 1 d . . . . .
H1 H 0.112640 0.773371 0.039472 0.045 Uiso 1 1 calc R . . . .
N2 N -0.0774(2) 0.4823(2) 0.12057(12) 0.0380(4) Uani 1 1 d . . . . .
H2A H -0.209466 0.427501 0.107661 0.046 Uiso 1 1 calc R . . . .
C1 C 0.5257(3) 0.7757(2) 0.84193(14) 0.0351(4) Uani 1 1 d . . . . .
C2 C 0.6285(3) 0.8269(2) 0.77325(13) 0.0333(4) Uani 1 1 d . . . . .
C3 C 0.7371(3) 0.9685(2) 0.77974(13) 0.0347(4) Uani 1 1 d . . . . .
H3 H 0.744390 1.035521 0.827863 0.042 Uiso 1 1 calc R . . . .
C4 C 0.8350(3) 1.0117(2) 0.71548(14) 0.0342(4) Uani 1 1 d . . . . .
H4 H 0.908121 1.108541 0.719873 0.041 Uiso 1 1 calc R . . . .
C5 C 0.8269(3) 0.9144(2) 0.64470(13) 0.0329(4) Uani 1 1 d . . . . .
C6 C 0.7157(3) 0.7725(2) 0.63821(13) 0.0341(4) Uani 1 1 d . . . . .
H6 H 0.707668 0.705350 0.590018 0.041 Uiso 1 1 calc R . . . .
C7 C 0.6176(3) 0.7298(2) 0.70185(14) 0.0350(4) Uani 1 1 d . . . . .
H7 H 0.542016 0.633519 0.696790 0.042 Uiso 1 1 calc R . . . .
C8 C 0.9233(3) 0.9587(2) 0.57319(13) 0.0318(4) Uani 1 1 d . . . . .
C9 C 0.8296(3) 0.9036(2) 0.48610(14) 0.0326(4) Uani 1 1 d . . . . .
H9 H 0.711115 0.836056 0.476586 0.039 Uiso 1 1 calc R . . . .
C10 C 0.8999(3) 0.9421(2) 0.41278(13) 0.0324(4) Uani 1 1 d . . . . .
C11 C 0.7791(3) 0.8806(2) 0.32513(13) 0.0321(4) Uani 1 1 d . . . . .
C12 C 0.7542(3) 0.9659(2) 0.26216(14) 0.0342(4) Uani 1 1 d . . . . .
H12 H 0.822552 1.064580 0.273752 0.041 Uiso 1 1 calc R . . . .
C13 C 0.6314(3) 0.9082(2) 0.18339(13) 0.0334(4) Uani 1 1 d . . . . .
H13 H 0.616451 0.967346 0.141275 0.040 Uiso 1 1 calc R . . . .
C14 C 0.5290(3) 0.7634(2) 0.16527(13) 0.0319(4) Uani 1 1 d . . . . .
C15 C 0.5550(3) 0.6773(2) 0.22686(13) 0.0335(4) Uani 1 1 d . . . . .
H15 H 0.487627 0.578455 0.214691 0.040 Uiso 1 1 calc R . . . .
C16 C 0.6784(3) 0.7350(2) 0.30574(13) 0.0334(4) Uani 1 1 d . . . . .
H16 H 0.694969 0.675270 0.347168 0.040 Uiso 1 1 calc R . . . .
C17 C 0.3865(3) 0.7037(2) 0.08182(13) 0.0321(4) Uani 1 1 d . . . . .
C18 C -0.0486(3) 0.6278(3) 0.15872(15) 0.0440(5) Uani 1 1 d . . . . .
H18A H 0.080313 0.679744 0.184596 0.053 Uiso 1 1 calc R . . . .
H18B H -0.116027 0.625674 0.206074 0.053 Uiso 1 1 calc R . . . .
C19 C -0.1120(3) 0.7027(3) 0.08726(17) 0.0446(5) Uani 1 1 d . . . . .
H19A H -0.241996 0.653065 0.063032 0.053 Uiso 1 1 calc R . . . .
H19B H -0.091560 0.801030 0.112380 0.053 Uiso 1 1 calc R . . . .
C20 C -0.0882(3) 0.7447(2) -0.06506(17) 0.0442(5) Uani 1 1 d . . . . .
H20A H -0.086671 0.842022 -0.052125 0.053 Uiso 1 1 calc R . . . .
H20B H -0.214515 0.680415 -0.086700 0.053 Uiso 1 1 calc R . . . .
C21 C 0.0161(3) 0.7386(3) -0.13658(17) 0.0476(6) Uani 1 1 d . . . . .
H21A H 0.145262 0.789560 -0.110689 0.057 Uiso 1 1 calc R . . . .
H21B H -0.018616 0.790615 -0.182760 0.057 Uiso 1 1 calc R . . . .
C22 C 0.0088(3) 0.4090(3) 0.18057(15) 0.0457(5) Uani 1 1 d . . . . .
H22A H -0.043364 0.400744 0.233608 0.055 Uiso 1 1 calc R . . . .
H22B H 0.138474 0.466022 0.199539 0.055 Uiso 1 1 calc R . . . .
O1A O 0.6965(3) 0.5306(2) 0.46490(12) 0.0514(4) Uani 1 1 d . . . . .
N1A N 0.7436(3) 0.3325(3) 0.4997(2) 0.0593(6) Uani 1 1 d . . . . .
C1A C 0.6871(4) 0.4398(3) 0.51099(18) 0.0474(5) Uani 1 1 d . . . . .
H1A H 0.634184 0.445654 0.560237 0.057 Uiso 1 1 calc R . . . .
C2A C 0.8219(5) 0.3135(5) 0.4257(3) 0.0807(11) Uani 1 1 d . . . . .
H2AA H 0.744537 0.225117 0.386905 0.121 Uiso 1 1 calc GR . . . .
H2AB H 0.940384 0.309363 0.446669 0.121 Uiso 1 1 calc GR . . . .
H2AC H 0.834051 0.393155 0.393076 0.121 Uiso 1 1 calc GR . . . .
C3A C 0.7271(7) 0.2321(5) 0.5628(4) 0.0978(15) Uani 1 1 d . . . . .
H3AA H 0.846083 0.232651 0.588400 0.147 Uiso 1 1 calc GR . . . .
H3AB H 0.650361 0.136781 0.532514 0.147 Uiso 1 1 calc GR . . . .
H3AC H 0.673754 0.259991 0.609686 0.147 Uiso 1 1 calc GR . . . .


_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 O4 2.2046(15) 2_565 ?
Zn1 O4 2.2046(15) . ?
Zn1 N1 2.1080(18) . ?
Zn1 N1 2.1080(18) 2_565 ?
Zn1 N2 2.0876(18) 2_565 ?
Zn1 N2 2.0876(18) . ?
O1 C1 1.213(3) . ?
O2 H2 0.8400 . ?
O2 C1 1.321(3) . ?
O3 C17 1.257(3) . ?
O4 C17 1.259(3) . ?
N1 H1 1.0000 . ?
N1 C19 1.471(3) . ?
N1 C20 1.481(3) . ?
N2 H2A 1.0000 . ?
N2 C18 1.472(3) . ?
N2 C22 1.478(3) . ?
C1 C2 1.491(3) . ?
C2 C3 1.393(3) . ?
C2 C7 1.394(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.396(3) . ?
C5 C6 1.401(3) . ?
C5 C8 1.486(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.386(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.403(3) . ?
C8 C10 1.411(3) 2_776 ?
C9 H9 0.9500 . ?
C9 C10 1.392(3) . ?
C10 C11 1.485(3) . ?
C11 C12 1.402(3) . ?
C11 C16 1.402(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.398(3) . ?
C14 C15 1.394(3) . ?
C14 C17 1.509(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(3) . ?
C16 H16 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.522(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.522(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.530(4) 2_565 ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
O1A C1A 1.210(3) . ?
N1A C1A 1.333(4) . ?
N1A C2A 1.440(5) . ?
N1A C3A 1.471(5) . ?
C1A H1A 0.9500 . ?
C2A H2AA 0.9800 . ?
C2A H2AB 0.9800 . ?
C2A H2AC 0.9800 . ?
C3A H3AA 0.9800 . ?
C3A H3AB 0.9800 . ?
C3A H3AC 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
O4 Zn1 O4 180.0 . 2_565 ?
N1 Zn1 O4 91.95(7) 2_565 2_565 ?
N1 Zn1 O4 88.05(7) 2_565 . ?
N1 Zn1 O4 88.05(7) . 2_565 ?
N1 Zn1 O4 91.95(7) . . ?
N1 Zn1 N1 180.0 2_565 . ?
N2 Zn1 O4 93.20(7) . 2_565 ?
N2 Zn1 O4 86.80(7) . . ?
N2 Zn1 O4 93.20(7) 2_565 . ?
N2 Zn1 O4 86.80(7) 2_565 2_565 ?
N2 Zn1 N1 85.37(8) 2_565 2_565 ?
N2 Zn1 N1 94.63(8) . 2_565 ?
N2 Zn1 N1 94.63(8) 2_565 . ?
N2 Zn1 N1 85.37(8) . . ?
N2 Zn1 N2 180.0 2_565 . ?
C1 O2 H2 109.5 . . ?
C17 O4 Zn1 123.51(13) . . ?
Zn1 N1 H1 107.8 . . ?
C19 N1 Zn1 104.68(14) . . ?
C19 N1 H1 107.8 . . ?
C19 N1 C20 114.39(19) . . ?
C20 N1 Zn1 114.00(15) . . ?
C20 N1 H1 107.8 . . ?
Zn1 N2 H2A 107.2 . . ?
C18 N2 Zn1 105.08(14) . . ?
C18 N2 H2A 107.2 . . ?
C18 N2 C22 113.58(19) . . ?
C22 N2 Zn1 115.99(15) . . ?
C22 N2 H2A 107.2 . . ?
O1 C1 O2 124.57(19) . . ?
O1 C1 C2 122.0(2) . . ?
O2 C1 C2 113.47(18) . . ?
C3 C2 C1 121.49(19) . . ?
C3 C2 C7 119.55(19) . . ?
C7 C2 C1 118.94(19) . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.84(19) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.80(19) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 118.94(19) . . ?
C4 C5 C8 121.87(19) . . ?
C6 C5 C8 119.07(19) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.21(19) . . ?
C7 C6 H6 119.9 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.65(19) . . ?
C6 C7 H7 119.7 . . ?
C9 C8 C5 117.84(19) . . ?
C9 C8 C10 117.98(19) . 2_776 ?
C10 C8 C5 124.10(19) 2_776 . ?
C8 C9 H9 118.0 . . ?
C10 C9 C8 123.91(19) . . ?
C10 C9 H9 118.0 . . ?
C8 C10 C11 124.70(18) 2_776 . ?
C9 C10 C8 118.11(19) . 2_776 ?
C9 C10 C11 117.12(19) . . ?
C12 C11 C10 121.54(18) . . ?
C12 C11 C16 118.39(19) . . ?
C16 C11 C10 119.96(18) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.78(19) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.48(19) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C17 119.81(18) . . ?
C15 C14 C13 119.15(19) . . ?
C15 C14 C17 120.98(18) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.39(19) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.80(19) . . ?
C15 C16 H16 119.6 . . ?
O3 C17 O4 124.56(19) . . ?
O3 C17 C14 118.37(18) . . ?
O4 C17 C14 116.98(17) . . ?
N2 C18 H18A 109.8 . . ?
N2 C18 H18B 109.8 . . ?
N2 C18 C19 109.46(18) . . ?
H18A C18 H18B 108.2 . . ?
C19 C18 H18A 109.8 . . ?
C19 C18 H18B 109.8 . . ?
N1 C19 C18 109.24(19) . . ?
N1 C19 H19A 109.8 . . ?
N1 C19 H19B 109.8 . . ?
C18 C19 H19A 109.8 . . ?
C18 C19 H19B 109.8 . . ?
H19A C19 H19B 108.3 . . ?
N1 C20 H20A 109.2 . . ?
N1 C20 H20B 109.2 . . ?
N1 C20 C21 112.08(19) . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
C20 C21 H21A 108.2 . . ?
C20 C21 H21B 108.2 . . ?
C20 C21 C22 116.37(19) . 2_565 ?
H21A C21 H21B 107.3 . . ?
C22 C21 H21A 108.2 2_565 . ?
C22 C21 H21B 108.2 2_565 . ?
N2 C22 C21 111.78(19) . 2_565 ?
N2 C22 H22A 109.3 . . ?
N2 C22 H22B 109.3 . . ?
C21 C22 H22A 109.3 2_565 . ?
C21 C22 H22B 109.3 2_565 . ?
H22A C22 H22B 107.9 . . ?
C1A N1A C2A 120.5(3) . . ?
C1A N1A C3A 120.3(3) . . ?
C2A N1A C3A 119.2(3) . . ?
O1A C1A N1A 126.6(3) . . ?
O1A C1A H1A 116.7 . . ?
N1A C1A H1A 116.7 . . ?
N1A C2A H2AA 109.5 . . ?
N1A C2A H2AB 109.5 . . ?
N1A C2A H2AC 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
N1A C3A H3AA 109.5 . . ?
N1A C3A H3AB 109.5 . . ?
N1A C3A H3AC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 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
_geom_hbond_publ_flag
O2 H2 O3 0.84 1.72 2.556(2) 175.3 1_556 yes
N1 H1 O3 1.00 2.17 2.967(2) 135.3 . yes
N2 H2A O1 1.00 2.04 2.899(3) 142.7 2_566 yes

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 O4 C17 O3 -26.5(3) . . . . ?
Zn1 O4 C17 C14 150.07(13) . . . . ?
Zn1 N1 C19 C18 41.66(19) . . . . ?
Zn1 N1 C20 C21 -57.5(2) . . . . ?
Zn1 N2 C18 C19 41.9(2) . . . . ?
Zn1 N2 C22 C21 -55.1(2) . . . 2_565 ?
O1 C1 C2 C3 174.1(2) . . . . ?
O1 C1 C2 C7 -7.0(3) . . . . ?
O2 C1 C2 C3 -7.0(3) . . . . ?
O2 C1 C2 C7 171.91(18) . . . . ?
N1 C20 C21 C22 73.0(3) . . . 2_565 ?
N2 C18 C19 N1 -58.8(2) . . . . ?
C1 C2 C3 C4 178.24(19) . . . . ?
C1 C2 C7 C6 -177.85(18) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C2 C7 C6 1.1(3) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C3 C4 C5 C8 177.18(18) . . . . ?
C4 C5 C6 C7 -0.8(3) . . . . ?
C4 C5 C8 C9 -134.3(2) . . . . ?
C4 C5 C8 C10 42.5(3) . . . 2_776 ?
C5 C6 C7 C2 -0.3(3) . . . . ?
C5 C8 C9 C10 176.23(18) . . . . ?
C6 C5 C8 C9 41.7(3) . . . . ?
C6 C5 C8 C10 -141.6(2) . . . 2_776 ?
C7 C2 C3 C4 -0.6(3) . . . . ?
C8 C5 C6 C7 -176.87(18) . . . . ?
C8 C9 C10 C8 0.7(3) . . . 2_776 ?
C8 C9 C10 C11 -176.32(19) . . . . ?
C8 C10 C11 C12 -48.5(3) 2_776 . . . ?
C8 C10 C11 C16 135.4(2) 2_776 . . . ?
C9 C10 C11 C12 128.3(2) . . . . ?
C9 C10 C11 C16 -47.7(3) . . . . ?
C10 C8 C9 C10 -0.7(3) 2_776 . . . ?
C10 C11 C12 C13 -175.21(19) . . . . ?
C10 C11 C16 C15 175.10(19) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C11 C16 C15 -1.1(3) . . . . ?
C12 C13 C14 C15 -1.3(3) . . . . ?
C12 C13 C14 C17 175.76(18) . . . . ?
C13 C14 C15 C16 1.2(3) . . . . ?
C13 C14 C17 O3 8.3(3) . . . . ?
C13 C14 C17 O4 -168.46(18) . . . . ?
C14 C15 C16 C11 0.0(3) . . . . ?
C15 C14 C17 O3 -174.62(18) . . . . ?
C15 C14 C17 O4 8.6(3) . . . . ?
C16 C11 C12 C13 0.9(3) . . . . ?
C17 C14 C15 C16 -175.89(18) . . . . ?
C18 N2 C22 C21 -176.97(18) . . . 2_565 ?
C19 N1 C20 C21 -177.89(18) . . . . ?
C20 N1 C19 C18 167.14(18) . . . . ?
C22 N2 C18 C19 169.67(18) . . . . ?
C2A N1A C1A O1A -1.4(5) . . . . ?
C3A N1A C1A O1A 178.4(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_olex2_submission_original_sample_id ND-ZN-MOF
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ada252
_database_code_depnum_ccdc_archive 'CCDC 2045787'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2020-11-22 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;
_audit_creation_date             2020-02-05
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H44 N4 O8 Zn'
_chemical_formula_sum            'C44 H44 N4 O8 Zn'
_chemical_formula_weight         822.20
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2782(5)
_cell_length_b                   10.0936(6)
_cell_length_c                   15.6910(9)
_cell_angle_alpha                95.712(2)
_cell_angle_beta                 99.174(2)
_cell_angle_gamma                111.463(2)
_cell_volume                     1186.65(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.005
_cell_measurement_theta_min      4.779
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.750
_exptl_absorpt_coefficient_mu    1.129
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1185 before and 0.0592 after correction.
The Ratio of minimum to maximum transmission is 0.7012.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             430
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 180.0 degree
scan in 180 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23541
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.182
_diffrn_reflns_theta_min         4.779
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Microfocus Source'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4181
_reflns_number_total             4379
_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 (2019) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2019) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.050
_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)+(0.0565P)²+0.5290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1027
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C17(H17), C18(H18), C20(H20),
 C21(H21)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Zn1 Zn 1.000000 0.500000 1.000000 0.02661(11) Uani 1 2 d S . P . .
O1 O 0.72574(15) 0.41885(12) 0.92281(7) 0.0305(3) Uani 1 1 d . . . . .
O2 O 0.61308(15) 0.21277(13) 0.97360(7) 0.0308(3) Uani 1 1 d . . . . .
O3 O 0.56465(17) 0.34816(13) 0.16117(8) 0.0384(3) Uani 1 1 d . . . . .
O4 O 0.42491(17) 0.12107(13) 0.08705(7) 0.0331(3) Uani 1 1 d . . . . .
N1 N 1.0110(2) 0.29444(16) 0.97430(10) 0.0331(3) Uani 1 1 d . . . . .
N2 N 0.9179(2) 0.46845(17) 1.11794(9) 0.0331(3) Uani 1 1 d . . . . .
C1 C 0.9975(3) 0.3880(2) 1.17276(12) 0.0425(5) Uani 1 1 d . . . . .
H1A H 0.941719 0.372065 1.224171 0.051 Uiso 1 1 calc R U . . .
H1B H 1.125790 0.446923 1.194611 0.051 Uiso 1 1 calc R U . . .
C2 C 0.9744(2) 0.2422(2) 1.12292(13) 0.0438(5) Uani 1 1 d . . . . .
H2A H 1.006130 0.185667 1.165918 0.053 Uiso 1 1 calc R U . . .
H2B H 0.847158 0.189465 1.095209 0.053 Uiso 1 1 calc R U . . .
C3 C 1.0821(2) 0.2462(2) 1.05220(13) 0.0410(4) Uani 1 1 d . . . . .
H3A H 1.207099 0.312721 1.076225 0.049 Uiso 1 1 calc R U . . .
H3B H 1.080267 0.148578 1.034844 0.049 Uiso 1 1 calc R U . . .
C4 C 0.9464(3) 0.6135(2) 1.16232(11) 0.0409(4) Uani 1 1 d . . . . .
H4A H 1.073689 0.666966 1.189803 0.049 Uiso 1 1 calc R U . . .
H4B H 0.877310 0.604746 1.208965 0.049 Uiso 1 1 calc R U . . .
C5 C 1.1122(2) 0.3049(2) 0.90404(12) 0.0413(4) Uani 1 1 d . . . . .
H5A H 1.091369 0.206792 0.874811 0.050 Uiso 1 1 calc R U . . .
H5B H 1.240765 0.355954 0.929420 0.050 Uiso 1 1 calc R U . . .
C6 C 0.6116(2) 0.29356(18) 0.91746(10) 0.0273(3) Uani 1 1 d . . . . .
C7 C 0.4693(2) 0.23258(18) 0.83428(10) 0.0267(3) Uani 1 1 d . . . . .
C8 C 0.3656(2) 0.08559(18) 0.81313(10) 0.0290(3) Uani 1 1 d . . . . .
H8 H 0.378565 0.023553 0.853085 0.035 Uiso 1 1 calc R U . . .
C9 C 0.2430(2) 0.02845(18) 0.73406(10) 0.0302(3) Uani 1 1 d . . . . .
H9 H 0.173407 -0.072410 0.720267 0.036 Uiso 1 1 calc R U . . .
C10 C 0.2213(2) 0.11782(18) 0.67473(10) 0.0288(3) Uani 1 1 d . . . . .
C11 C 0.3236(2) 0.26591(19) 0.69723(10) 0.0306(3) Uani 1 1 d . . . . .
H11 H 0.308858 0.328486 0.658016 0.037 Uiso 1 1 calc R U . . .
C12 C 0.4468(2) 0.32306(18) 0.77610(10) 0.0290(3) Uani 1 1 d . . . . .
H12 H 0.515656 0.424018 0.790380 0.035 Uiso 1 1 calc R U . . .
C13 C 0.1010(2) 0.05725(18) 0.58668(10) 0.0298(3) Uani 1 1 d . . . . .
C14 C 0.1714(2) 0.09698(19) 0.51366(10) 0.0309(3) Uani 1 1 d . . . . .
H14 H 0.290578 0.164794 0.523094 0.037 Uiso 1 1 calc R U . . .
C15 C 0.0760(2) 0.04231(18) 0.42743(10) 0.0307(3) Uani 1 1 d . . . . .
C16 C 0.1703(2) 0.08742(19) 0.35548(10) 0.0295(3) Uani 1 1 d . . . . .
C17 C 0.1703(2) -0.01473(19) 0.28823(10) 0.0315(4) Uani 1 1 d . . . . .
H17 H 0.105104 -0.114586 0.287044 0.038 Uiso 1 1 calc R U . . .
C18 C 0.2641(2) 0.02795(19) 0.22348(10) 0.0314(4) Uani 1 1 d . . . . .
H18 H 0.261704 -0.042689 0.177984 0.038 Uiso 1 1 calc R U . . .
C19 C 0.3616(2) 0.17329(18) 0.22450(10) 0.0293(3) Uani 1 1 d . . . . .
C20 C 0.3641(2) 0.27590(19) 0.29206(11) 0.0318(4) Uani 1 1 d . . . . .
H20 H 0.431606 0.375529 0.293822 0.038 Uiso 1 1 calc R U . . .
C21 C 0.2693(2) 0.23335(19) 0.35620(10) 0.0323(4) Uani 1 1 d . . . . .
H21 H 0.271334 0.304256 0.401443 0.039 Uiso 1 1 calc R U . . .
C22 C 0.4620(2) 0.22433(19) 0.15523(10) 0.0302(3) Uani 1 1 d . . . . .
H2 H 0.811(3) 0.422(2) 1.1085(14) 0.033(5) Uiso 1 1 d . . . . .
H1 H 0.904(3) 0.241(3) 0.9565(15) 0.043(6) Uiso 1 1 d . . . . .
H4 H 0.489(3) 0.157(3) 0.0489(17) 0.054(7) Uiso 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
Zn1 O1 2.2039(11) . ?
Zn1 O1 2.2039(11) 2_767 ?
Zn1 N1 2.1117(15) . ?
Zn1 N1 2.1117(15) 2_767 ?
Zn1 N2 2.0853(14) . ?
Zn1 N2 2.0854(14) 2_767 ?
O1 C6 1.256(2) . ?
O2 C6 1.260(2) . ?
O3 C22 1.211(2) . ?
O4 C22 1.328(2) . ?
O4 H4 0.88(3) . ?
N1 C3 1.475(2) . ?
N1 C5 1.477(2) . ?
N1 H1 0.84(2) . ?
N2 C1 1.478(2) . ?
N2 C4 1.475(2) . ?
N2 H2 0.81(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.526(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.525(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.516(3) 2_767 ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.513(2) . ?
C7 C8 1.388(2) . ?
C7 C12 1.392(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.395(2) . ?
C10 C11 1.396(2) . ?
C10 C13 1.490(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.395(2) . ?
C13 C15 1.407(2) 2_556 ?
C14 H14 0.9500 . ?
C14 C15 1.397(2) . ?
C15 C16 1.488(2) . ?
C16 C17 1.400(2) . ?
C16 C21 1.397(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(2) . ?
C19 C20 1.398(2) . ?
C19 C22 1.491(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.380(2) . ?
C21 H21 0.9500 . ?

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 Zn1 O1 180.00(4) 2_767 . ?
N1 Zn1 O1 88.45(5) . 2_767 ?
N1 Zn1 O1 88.45(5) 2_767 . ?
N1 Zn1 O1 91.55(5) 2_767 2_767 ?
N1 Zn1 O1 91.55(5) . . ?
N1 Zn1 N1 180.0 2_767 . ?
N2 Zn1 O1 86.83(5) 2_767 . ?
N2 Zn1 O1 93.17(5) 2_767 2_767 ?
N2 Zn1 O1 93.17(5) . . ?
N2 Zn1 O1 86.83(5) . 2_767 ?
N2 Zn1 N1 85.39(6) 2_767 . ?
N2 Zn1 N1 85.39(6) . 2_767 ?
N2 Zn1 N1 94.62(6) 2_767 2_767 ?
N2 Zn1 N1 94.61(6) . . ?
N2 Zn1 N2 180.0 . 2_767 ?
C6 O1 Zn1 124.72(10) . . ?
C22 O4 H4 108.8(17) . . ?
Zn1 N1 H1 102.0(16) . . ?
C3 N1 Zn1 114.39(11) . . ?
C3 N1 C5 114.56(15) . . ?
C3 N1 H1 108.4(16) . . ?
C5 N1 Zn1 104.50(11) . . ?
C5 N1 H1 112.3(15) . . ?
Zn1 N2 H2 110.1(15) . . ?
C1 N2 Zn1 116.03(12) . . ?
C1 N2 H2 104.8(15) . . ?
C4 N2 Zn1 105.30(11) . . ?
C4 N2 C1 114.17(14) . . ?
C4 N2 H2 106.0(15) . . ?
N2 C1 H1A 109.1 . . ?
N2 C1 H1B 109.1 . . ?
N2 C1 C2 112.56(14) . . ?
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
C1 C2 H2A 108.2 . . ?
C1 C2 H2B 108.2 . . ?
H2A C2 H2B 107.3 . . ?
C3 C2 C1 116.52(16) . . ?
C3 C2 H2A 108.2 . . ?
C3 C2 H2B 108.2 . . ?
N1 C3 C2 111.63(15) . . ?
N1 C3 H3A 109.3 . . ?
N1 C3 H3B 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
N2 C4 H4A 109.8 . . ?
N2 C4 H4B 109.8 . . ?
N2 C4 C5 109.39(14) . 2_767 ?
H4A C4 H4B 108.2 . . ?
C5 C4 H4A 109.8 2_767 . ?
C5 C4 H4B 109.8 2_767 . ?
N1 C5 C4 109.57(15) . 2_767 ?
N1 C5 H5A 109.8 . . ?
N1 C5 H5B 109.8 . . ?
C4 C5 H5A 109.8 2_767 . ?
C4 C5 H5B 109.8 2_767 . ?
H5A C5 H5B 108.2 . . ?
O1 C6 O2 124.93(14) . . ?
O1 C6 C7 116.94(14) . . ?
O2 C6 C7 118.00(14) . . ?
C8 C7 C6 120.65(14) . . ?
C8 C7 C12 119.28(14) . . ?
C12 C7 C6 120.01(15) . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.57(15) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.60(15) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C11 118.47(14) . . ?
C9 C10 C13 121.38(15) . . ?
C11 C10 C13 120.04(15) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 120.97(15) . . ?
C12 C11 H11 119.5 . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 120.09(15) . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C10 117.66(15) . . ?
C14 C13 C15 118.17(15) . 2_556 ?
C15 C13 C10 124.10(15) 2_556 . ?
C13 C14 H14 118.3 . . ?
C13 C14 C15 123.45(16) . . ?
C15 C14 H14 118.3 . . ?
C13 C15 C16 123.60(14) 2_556 . ?
C14 C15 C13 118.37(15) . 2_556 ?
C14 C15 C16 117.95(15) . . ?
C17 C16 C15 121.21(15) . . ?
C21 C16 C15 120.38(15) . . ?
C21 C16 C17 118.32(15) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.82(16) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.49(15) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C20 119.06(15) . . ?
C18 C19 C22 122.31(15) . . ?
C20 C19 C22 118.63(15) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.42(16) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.88(15) . . ?
C20 C21 H21 119.6 . . ?
O3 C22 O4 124.29(15) . . ?
O3 C22 C19 122.63(15) . . ?
O4 C22 C19 113.07(14) . . ?

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
C1 H1B O1 0.99 2.60 3.116(2) 112.7 2_767 yes
C2 H2B O2 0.99 2.59 3.391(2) 138.3 . yes
C3 H3A O1 0.99 2.56 3.117(2) 115.7 2_767 yes
N2 H2 O3 0.81(2) 2.23(2) 2.947(2) 148(2) 1_556 yes
N1 H1 O2 0.84(2) 2.38(2) 3.0870(19) 143(2) . yes
O4 H4 O2 0.88(3) 1.69(3) 2.5708(16) 175(2) 1_554 yes

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 C6 O2 23.9(2) . . . . ?
Zn1 O1 C6 C7 -151.82(10) . . . . ?
Zn1 N1 C3 C2 57.70(18) . . . . ?
Zn1 N1 C5 C4 -41.28(16) . . . 2_767 ?
Zn1 N2 C1 C2 -53.92(18) . . . . ?
Zn1 N2 C4 C5 41.86(16) . . . 2_767 ?
O1 C6 C7 C8 164.14(15) . . . . ?
O1 C6 C7 C12 -13.0(2) . . . . ?
O2 C6 C7 C8 -11.9(2) . . . . ?
O2 C6 C7 C12 171.03(15) . . . . ?
N2 C1 C2 C3 70.3(2) . . . . ?
C1 N2 C4 C5 170.28(15) . . . 2_767 ?
C1 C2 C3 N1 -72.9(2) . . . . ?
C3 N1 C5 C4 -167.23(15) . . . 2_767 ?
C4 N2 C1 C2 -176.67(15) . . . . ?
C5 N1 C3 C2 178.33(15) . . . . ?
C6 C7 C8 C9 -175.79(15) . . . . ?
C6 C7 C12 C11 176.09(15) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C8 C7 C12 C11 -1.1(2) . . . . ?
C8 C9 C10 C11 -0.9(2) . . . . ?
C8 C9 C10 C13 175.11(15) . . . . ?
C9 C10 C11 C12 1.1(2) . . . . ?
C9 C10 C13 C14 -126.74(18) . . . . ?
C9 C10 C13 C15 50.2(2) . . . 2_556 ?
C10 C11 C12 C7 -0.2(3) . . . . ?
C10 C13 C14 C15 176.59(16) . . . . ?
C11 C10 C13 C14 49.2(2) . . . . ?
C11 C10 C13 C15 -133.92(18) . . . 2_556 ?
C12 C7 C8 C9 1.3(2) . . . . ?
C13 C10 C11 C12 -174.88(15) . . . . ?
C13 C14 C15 C13 0.5(3) . . . 2_556 ?
C13 C14 C15 C16 -176.60(16) . . . . ?
C13 C15 C16 C17 -49.7(2) 2_556 . . . ?
C13 C15 C16 C21 133.76(18) 2_556 . . . ?
C14 C15 C16 C17 127.24(18) . . . . ?
C14 C15 C16 C21 -49.3(2) . . . . ?
C15 C13 C14 C15 -0.5(3) 2_556 . . . ?
C15 C16 C17 C18 -177.45(15) . . . . ?
C15 C16 C21 C20 176.89(16) . . . . ?
C16 C17 C18 C19 0.6(3) . . . . ?
C17 C16 C21 C20 0.3(2) . . . . ?
C17 C18 C19 C20 0.2(2) . . . . ?
C17 C18 C19 C22 -178.90(15) . . . . ?
C18 C19 C20 C21 -0.8(2) . . . . ?
C18 C19 C22 O3 -170.57(16) . . . . ?
C18 C19 C22 O4 10.3(2) . . . . ?
C19 C20 C21 C16 0.6(3) . . . . ?
C20 C19 C22 O3 10.3(2) . . . . ?
C20 C19 C22 O4 -168.79(14) . . . . ?
C21 C16 C17 C18 -0.9(2) . . . . ?
C22 C19 C20 C21 178.35(15) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.889 -0.630 0.500 331.1 19.6 '0.5 C3H7NO'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ada200
_database_code_depnum_ccdc_archive 'CCDC 2045791'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2020-11-22 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;
_audit_creation_date             2019-06-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H44 Cu N4 O8, 2(C3 H7 N O)'
_chemical_formula_sum            'C50 H58 Cu N6 O10'
_chemical_formula_weight         966.56
_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 0.0181 0.0091 '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 -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0072(3)
_cell_length_b                   10.2227(3)
_cell_length_c                   15.6669(5)
_cell_angle_alpha                95.110(1)
_cell_angle_beta                 98.690(1)
_cell_angle_gamma                109.430(1)
_cell_volume                     1182.07(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9987
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.108
_cell_measurement_theta_min      4.639
_shelx_estimated_absorpt_T_max   0.880
_shelx_estimated_absorpt_T_min   0.832
_exptl_absorpt_coefficient_mu    1.191
_exptl_absorpt_correction_T_max  0.5220
_exptl_absorpt_correction_T_min  0.4538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1420 before and 0.0316 after correction. The Ratio of minimum to maximum transmission is 0.8693. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             509
_exptl_crystal_recrystallization_method 'crystallized from DMF/H2O'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 180.0 degree
scan in 180 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30946
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.101
_diffrn_reflns_theta_min         4.639
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Microfocus Source'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4264
_reflns_number_total             4334
_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 (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4334
_refine_ls_number_restraints     192
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.100
_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)+(0.0367P)²+1.1455P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0875
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.002 and sigma
for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C17(H17), C18(H18), C20(H20),
 C21(H21), C1A(H1AA)
3.c Idealised Me refined as rotating group:
 C2A(H2AA,H2AB,H2AC), C3A(H3AA,H3AB,H3AC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 1.000000 0.500000 1.000000 0.01263(10) Uani 1 2 d S TU P . .
O1 O 0.68689(15) 0.42305(12) 0.92836(7) 0.0193(2) Uani 1 1 d . U . . .
O2 O 0.61954(15) 0.20877(12) 0.96700(7) 0.0171(2) Uani 1 1 d . U . . .
O3 O 0.44743(16) 0.13445(12) 0.08821(8) 0.0196(3) Uani 1 1 d . U . . .
O4 O 0.59180(16) 0.34861(12) 0.16613(8) 0.0236(3) Uani 1 1 d . U . . .
N1 N 1.06616(19) 0.50895(16) 0.88100(9) 0.0188(3) Uani 1 1 d . U . . .
N2 N 1.00959(19) 0.30363(14) 0.98791(10) 0.0184(3) Uani 1 1 d . U . . .
C1 C 0.9822(2) 0.5812(2) 0.81950(11) 0.0254(4) Uani 1 1 d . U . . .
H1A H 0.850946 0.528067 0.803001 0.031 Uiso 1 1 calc R . . . .
H1B H 1.033552 0.582928 0.765772 0.031 Uiso 1 1 calc R . . . .
C2 C 1.0365(2) 0.36357(19) 0.84341(11) 0.0243(4) Uani 1 1 d . U . . .
H2A H 1.103227 0.363773 0.795092 0.029 Uiso 1 1 calc R . . . .
H2B H 0.906490 0.312629 0.819863 0.029 Uiso 1 1 calc R . . . .
C3 C 1.1027(2) 0.29234(19) 0.91457(12) 0.0240(3) Uani 1 1 d . U . . .
H3A H 1.076261 0.192449 0.892239 0.029 Uiso 1 1 calc R . . . .
H3B H 1.234851 0.338062 0.934449 0.029 Uiso 1 1 calc R . . . .
C4 C 1.0864(2) 0.25869(19) 1.06697(13) 0.0247(4) Uani 1 1 d . U . . .
H4A H 1.215307 0.318050 1.085954 0.030 Uiso 1 1 calc R . . . .
H4B H 1.079391 0.160428 1.052838 0.030 Uiso 1 1 calc R . . . .
C5 C 0.9872(2) 0.2694(2) 1.14117(13) 0.0284(4) Uani 1 1 d . U . . .
H5A H 1.026160 0.220514 1.187814 0.034 Uiso 1 1 calc R . . . .
H5B H 0.856325 0.219843 1.119289 0.034 Uiso 1 1 calc R . . . .
C6 C 0.5983(2) 0.29501(17) 0.91584(10) 0.0143(3) Uani 1 1 d . U . . .
C7 C 0.4621(2) 0.23363(16) 0.83175(10) 0.0133(3) Uani 1 1 d . U . . .
C8 C 0.4335(2) 0.31936(16) 0.77101(10) 0.0147(3) Uani 1 1 d . U . . .
H8 H 0.496356 0.417779 0.783712 0.018 Uiso 1 1 calc R . . . .
C9 C 0.3140(2) 0.26238(16) 0.69223(10) 0.0142(3) Uani 1 1 d . U . . .
H9 H 0.296784 0.321794 0.651067 0.017 Uiso 1 1 calc R . . . .
C10 C 0.2186(2) 0.11767(16) 0.67300(10) 0.0134(3) Uani 1 1 d . U . . .
C11 C 0.2460(2) 0.03236(16) 0.73474(10) 0.0149(3) Uani 1 1 d . U . . .
H11 H 0.181194 -0.065837 0.722794 0.018 Uiso 1 1 calc R . . . .
C12 C 0.3666(2) 0.08957(16) 0.81313(10) 0.0144(3) Uani 1 1 d . U . . .
H12 H 0.384212 0.030384 0.854377 0.017 Uiso 1 1 calc R . . . .
C13 C 0.0987(2) 0.05649(16) 0.58592(10) 0.0134(3) Uani 1 1 d . U . . .
C14 C 0.1707(2) 0.09602(16) 0.51267(10) 0.0140(3) Uani 1 1 d . U . . .
H14 H 0.289263 0.163339 0.521508 0.017 Uiso 1 1 calc R . . . .
C15 C 0.0782(2) 0.04213(16) 0.42684(10) 0.0134(3) Uani 1 1 d . U . . .
C16 C 0.1768(2) 0.08794(16) 0.35510(10) 0.0139(3) Uani 1 1 d . U . . .
C17 C 0.1711(2) -0.00687(16) 0.28382(10) 0.0151(3) Uani 1 1 d . U . . .
H17 H 0.098273 -0.102890 0.279205 0.018 Uiso 1 1 calc R . . . .
C18 C 0.2702(2) 0.03702(17) 0.21960(10) 0.0157(3) Uani 1 1 d . U . . .
H18 H 0.264137 -0.028657 0.171305 0.019 Uiso 1 1 calc R . . . .
C19 C 0.3787(2) 0.17760(17) 0.22599(10) 0.0150(3) Uani 1 1 d . U . . .
C20 C 0.3880(2) 0.27268(17) 0.29763(11) 0.0167(3) Uani 1 1 d . U . . .
H20 H 0.463446 0.368158 0.302910 0.020 Uiso 1 1 calc R . . . .
C21 C 0.2877(2) 0.22844(17) 0.36127(10) 0.0160(3) Uani 1 1 d . U . . .
H21 H 0.294237 0.294246 0.409607 0.019 Uiso 1 1 calc R . . . .
C22 C 0.4845(2) 0.22947(17) 0.15740(10) 0.0162(3) Uani 1 1 d . U . . .
O1A O 0.3007(2) 0.46985(14) 0.53463(9) 0.0341(3) Uani 1 1 d . U . . .
N1A N 0.2559(2) 0.66746(18) 0.49766(13) 0.0386(4) Uani 1 1 d . U . . .
C1A C 0.3118(3) 0.5591(2) 0.48735(14) 0.0313(4) Uani 1 1 d . U . . .
H1AA H 0.365822 0.550830 0.438113 0.038 Uiso 1 1 calc R . . . .
C2A C 0.1768(4) 0.6905(3) 0.5720(2) 0.0658(8) Uani 1 1 d . U . . .
H2AA H 0.056602 0.693965 0.551700 0.099 Uiso 1 1 calc GR . . . .
H2AB H 0.253540 0.779588 0.608358 0.099 Uiso 1 1 calc GR . . . .
H2AC H 0.166507 0.613686 0.606433 0.099 Uiso 1 1 calc GR . . . .
C3A C 0.2713(4) 0.7643(3) 0.4334(3) 0.0750(10) Uani 1 1 d . U . . .
H3AA H 0.343044 0.859909 0.462454 0.112 Uiso 1 1 calc GR . . . .
H3AB H 0.150608 0.760607 0.406780 0.112 Uiso 1 1 calc GR . . . .
H3AC H 0.330465 0.737238 0.388067 0.112 Uiso 1 1 calc GR . . . .
H1 H 1.179(3) 0.553(2) 0.8915(13) 0.020(5) Uiso 1 1 d . . . . .
H2 H 0.897(3) 0.256(2) 0.9748(14) 0.022(5) Uiso 1 1 d . . . . .
H3 H 0.505(4) 0.164(3) 0.0486(18) 0.045(7) Uiso 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 O1 2.4175(11) . ?
Cu1 O1 2.4175(11) 2_767 ?
Cu1 N1 2.0153(13) . ?
Cu1 N1 2.0153(14) 2_767 ?
Cu1 N2 2.0275(13) . ?
Cu1 N2 2.0275(13) 2_767 ?
O1 C6 1.245(2) . ?
O2 C6 1.2780(19) . ?
O3 C22 1.315(2) . ?
O3 H3 0.85(3) . ?
O4 C22 1.216(2) . ?
N1 C1 1.479(2) . ?
N1 C2 1.476(2) . ?
N1 H1 0.84(2) . ?
N2 C3 1.477(2) . ?
N2 C4 1.478(2) . ?
N2 H2 0.85(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C5 1.520(3) 2_767 ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.509(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.519(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.511(2) . ?
C7 C8 1.394(2) . ?
C7 C12 1.395(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.386(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.401(2) . ?
C10 C11 1.399(2) . ?
C10 C13 1.492(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.393(2) . ?
C13 C15 1.411(2) 2_556 ?
C14 H14 0.9500 . ?
C14 C15 1.398(2) . ?
C15 C16 1.491(2) . ?
C16 C17 1.397(2) . ?
C16 C21 1.401(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.395(2) . ?
C19 C20 1.393(2) . ?
C19 C22 1.494(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(2) . ?
C21 H21 0.9500 . ?
O1A C1A 1.215(2) . ?
N1A C1A 1.332(3) . ?
N1A C2A 1.445(4) . ?
N1A C3A 1.463(3) . ?
C1A H1AA 0.9500 . ?
C2A H2AA 0.9800 . ?
C2A H2AB 0.9800 . ?
C2A H2AC 0.9800 . ?
C3A H3AA 0.9800 . ?
C3A H3AB 0.9800 . ?
C3A H3AC 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 Cu1 O1 180.0 2_767 . ?
N1 Cu1 O1 91.99(5) 2_767 . ?
N1 Cu1 O1 88.01(5) . . ?
N1 Cu1 O1 91.99(5) . 2_767 ?
N1 Cu1 O1 88.01(5) 2_767 2_767 ?
N1 Cu1 N1 180.0 . 2_767 ?
N1 Cu1 N2 93.74(6) 2_767 . ?
N1 Cu1 N2 86.26(6) 2_767 2_767 ?
N1 Cu1 N2 93.74(6) . 2_767 ?
N1 Cu1 N2 86.26(6) . . ?
N2 Cu1 O1 93.83(5) . . ?
N2 Cu1 O1 86.17(5) . 2_767 ?
N2 Cu1 O1 86.17(5) 2_767 . ?
N2 Cu1 O1 93.83(5) 2_767 2_767 ?
N2 Cu1 N2 180.0 . 2_767 ?
C6 O1 Cu1 117.97(10) . . ?
C22 O3 H3 113.5(18) . . ?
Cu1 N1 H1 104.2(14) . . ?
C1 N1 Cu1 118.38(11) . . ?
C1 N1 H1 107.6(14) . . ?
C2 N1 Cu1 106.48(10) . . ?
C2 N1 C1 112.29(14) . . ?
C2 N1 H1 107.2(14) . . ?
Cu1 N2 H2 99.6(14) . . ?
C3 N2 Cu1 106.18(10) . . ?
C3 N2 C4 112.65(14) . . ?
C3 N2 H2 112.4(14) . . ?
C4 N2 Cu1 117.31(11) . . ?
C4 N2 H2 108.1(14) . . ?
N1 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
N1 C1 C5 111.96(14) . 2_767 ?
H1A C1 H1B 107.9 . . ?
C5 C1 H1A 109.2 2_767 . ?
C5 C1 H1B 109.2 2_767 . ?
N1 C2 H2A 110.0 . . ?
N1 C2 H2B 110.0 . . ?
N1 C2 C3 108.33(14) . . ?
H2A C2 H2B 108.4 . . ?
C3 C2 H2A 110.0 . . ?
C3 C2 H2B 110.0 . . ?
N2 C3 C2 108.22(13) . . ?
N2 C3 H3A 110.1 . . ?
N2 C3 H3B 110.1 . . ?
C2 C3 H3A 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
N2 C4 H4A 109.3 . . ?
N2 C4 H4B 109.3 . . ?
N2 C4 C5 111.80(14) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C1 C5 H5A 108.7 2_767 . ?
C1 C5 H5B 108.7 2_767 . ?
C4 C5 C1 114.30(15) . 2_767 ?
C4 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
O1 C6 O2 124.95(14) . . ?
O1 C6 C7 118.33(14) . . ?
O2 C6 C7 116.62(14) . . ?
C8 C7 C6 120.58(14) . . ?
C8 C7 C12 119.20(14) . . ?
C12 C7 C6 120.19(13) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.64(14) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.36(14) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C13 119.86(13) . . ?
C11 C10 C9 118.77(14) . . ?
C11 C10 C13 121.28(14) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.71(14) . . ?
C12 C11 H11 119.6 . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.31(14) . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C10 117.07(14) . . ?
C14 C13 C15 118.41(14) . 2_556 ?
C15 C13 C10 124.47(14) 2_556 . ?
C13 C14 H14 118.2 . . ?
C13 C14 C15 123.65(15) . . ?
C15 C14 H14 118.2 . . ?
C13 C15 C16 124.44(14) 2_556 . ?
C14 C15 C13 117.94(14) . 2_556 ?
C14 C15 C16 117.56(14) . . ?
C17 C16 C15 121.95(14) . . ?
C17 C16 C21 118.42(14) . . ?
C21 C16 C15 119.51(14) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.03(14) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.01(15) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C22 121.62(14) . . ?
C20 C19 C18 119.48(14) . . ?
C20 C19 C22 118.89(14) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.26(15) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.79(15) . . ?
C20 C21 H21 119.6 . . ?
O3 C22 C19 113.18(14) . . ?
O4 C22 O3 124.77(15) . . ?
O4 C22 C19 122.05(15) . . ?
C1A N1A C2A 120.5(2) . . ?
C1A N1A C3A 120.7(2) . . ?
C2A N1A C3A 118.8(2) . . ?
O1A C1A N1A 126.5(2) . . ?
O1A C1A H1AA 116.8 . . ?
N1A C1A H1AA 116.8 . . ?
N1A C2A H2AA 109.5 . . ?
N1A C2A H2AB 109.5 . . ?
N1A C2A H2AC 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
N1A C3A H3AA 109.5 . . ?
N1A C3A H3AB 109.5 . . ?
N1A C3A H3AC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 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
_geom_hbond_publ_flag
C1 H1A O1 0.99 2.64 3.206(2) 116.7 . yes
C4 H4A O1 0.99 2.54 3.142(2) 119.1 2_767 yes
N1 H1 O4 0.84(2) 2.15(2) 2.8838(18) 144.5(19) 2_766 yes
N2 H2 O2 0.85(2) 2.09(2) 2.9019(18) 158.5(19) . yes
O3 H3 O2 0.85(3) 1.69(3) 2.5365(15) 175(3) 1_554 yes

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 C6 O2 34.08(19) . . . . ?
Cu1 O1 C6 C7 -142.29(10) . . . . ?
Cu1 N1 C1 C5 55.04(18) . . . 2_767 ?
Cu1 N1 C2 C3 -40.87(15) . . . . ?
Cu1 N2 C3 C2 -40.58(15) . . . . ?
Cu1 N2 C4 C5 56.99(17) . . . . ?
O1 C6 C7 C8 -1.7(2) . . . . ?
O1 C6 C7 C12 176.78(14) . . . . ?
O2 C6 C7 C8 -178.37(14) . . . . ?
O2 C6 C7 C12 0.1(2) . . . . ?
N1 C2 C3 N2 55.55(18) . . . . ?
N2 C4 C5 C1 -69.90(19) . . . 2_767 ?
C1 N1 C2 C3 -171.93(14) . . . . ?
C2 N1 C1 C5 179.78(14) . . . 2_767 ?
C3 N2 C4 C5 -179.27(14) . . . . ?
C4 N2 C3 C2 -170.28(14) . . . . ?
C6 C7 C8 C9 177.30(14) . . . . ?
C6 C7 C12 C11 -177.83(14) . . . . ?
C7 C8 C9 C10 0.8(2) . . . . ?
C8 C7 C12 C11 0.7(2) . . . . ?
C8 C9 C10 C11 0.1(2) . . . . ?
C8 C9 C10 C13 -176.38(14) . . . . ?
C9 C10 C11 C12 -0.6(2) . . . . ?
C9 C10 C13 C14 48.7(2) . . . . ?
C9 C10 C13 C15 -134.06(16) . . . 2_556 ?
C10 C11 C12 C7 0.2(2) . . . . ?
C10 C13 C14 C15 176.64(14) . . . . ?
C11 C10 C13 C14 -127.74(16) . . . . ?
C11 C10 C13 C15 49.5(2) . . . 2_556 ?
C12 C7 C8 C9 -1.2(2) . . . . ?
C13 C10 C11 C12 175.81(14) . . . . ?
C13 C14 C15 C13 0.8(2) . . . 2_556 ?
C13 C14 C15 C16 -176.40(14) . . . . ?
C13 C15 C16 C17 -42.0(2) 2_556 . . . ?
C13 C15 C16 C21 142.02(16) 2_556 . . . ?
C14 C15 C16 C17 135.00(16) . . . . ?
C14 C15 C16 C21 -41.0(2) . . . . ?
C15 C13 C14 C15 -0.8(2) 2_556 . . . ?
C15 C16 C17 C18 -177.17(14) . . . . ?
C15 C16 C21 C20 176.78(14) . . . . ?
C16 C17 C18 C19 0.5(2) . . . . ?
C17 C16 C21 C20 0.6(2) . . . . ?
C17 C18 C19 C20 0.7(2) . . . . ?
C17 C18 C19 C22 -178.79(14) . . . . ?
C18 C19 C20 C21 -1.2(2) . . . . ?
C18 C19 C22 O3 7.5(2) . . . . ?
C18 C19 C22 O4 -173.17(15) . . . . ?
C19 C20 C21 C16 0.5(2) . . . . ?
C20 C19 C22 O3 -171.97(14) . . . . ?
C20 C19 C22 O4 7.3(2) . . . . ?
C21 C16 C17 C18 -1.1(2) . . . . ?
C22 C19 C20 C21 178.31(14) . . . . ?
C2A N1A C1A O1A 1.7(3) . . . . ?
C3A N1A C1A O1A -177.5(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_olex2_submission_original_sample_id NR-172-2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ada251
_database_code_depnum_ccdc_archive 'CCDC 2045789'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2020-11-22 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;
_audit_creation_date             2020-01-27
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
Nour.Dissem@uqtr.ca
thierry.maris@umontreal.ca
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H44 Cu N4 O8'
_chemical_formula_sum            'C44 H44 Cu N4 O8'
_chemical_formula_weight         820.37
_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 0.0181 0.0091 '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 -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5883(4)
_cell_length_b                   9.4777(5)
_cell_length_c                   16.8623(10)
_cell_angle_alpha                81.516(2)
_cell_angle_beta                 80.992(2)
_cell_angle_gamma                72.616(2)
_cell_volume                     1136.51(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    100
_cell_measurement_theta_max      69.966
_cell_measurement_theta_min      4.918
_shelx_estimated_absorpt_T_max   0.907
_shelx_estimated_absorpt_T_min   0.834
_exptl_absorpt_coefficient_mu    1.107
_exptl_absorpt_correction_T_max  0.5220
_exptl_absorpt_correction_T_min  0.3966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0748 before and 0.0403 after correction.
The Ratio of minimum to maximum transmission is 0.7598.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             429
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 180.0 degree
scan in 180 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23181
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.108
_diffrn_reflns_theta_min         4.918
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Microfocus Source'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4041
_reflns_number_total             4214
_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 (2019) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2019) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.047
_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)+(0.0553P)²+0.4541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0938
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1), N2(H2A)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C5(H5), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.000000 0.000000 0.500000 0.02164(10) Uani 1 2 d S . P . .
O1 O 0.18816(14) 0.15982(11) 0.43907(6) 0.0276(2) Uani 1 1 d . . . . .
O2 O 0.18978(15) 0.39008(11) 0.45525(6) 0.0267(2) Uani 1 1 d . . . . .
O3 O 0.79999(14) 0.65186(12) 0.39683(6) 0.0289(2) Uani 1 1 d . . . . .
O4 O 0.59274(15) 0.87447(11) 0.37380(6) 0.0281(2) Uani 1 1 d . . . . .
N1 N 0.22513(16) -0.16500(13) 0.46450(7) 0.0245(3) Uani 1 1 d . . . . .
H1 H 0.325623 -0.117374 0.441089 0.029 Uiso 1 1 calc R U . . .
N2 N -0.09072(17) -0.00843(13) 0.39506(7) 0.0243(3) Uani 1 1 d . . . . .
H2A H -0.184287 -0.066158 0.408447 0.029 Uiso 1 1 calc R U . . .
C1 C 0.6028(2) 0.60090(16) -0.01122(9) 0.0258(3) Uani 1 1 d . . . . .
H1A H 0.672993 0.670747 -0.019033 0.031 Uiso 1 1 calc R U . . .
C2 C 0.5376(2) 0.55407(15) 0.06715(9) 0.0251(3) Uani 1 1 d . . . . .
C3 C 0.4320(2) 0.45166(16) 0.07854(9) 0.0253(3) Uani 1 1 d . . . . .
C4 C 0.5864(2) 0.60681(16) 0.13777(8) 0.0248(3) Uani 1 1 d . . . . .
C5 C 0.5296(2) 0.75706(17) 0.14988(9) 0.0288(3) Uani 1 1 d . . . . .
H5 H 0.467516 0.828635 0.110251 0.035 Uiso 1 1 calc R U . . .
C6 C 0.5627(2) 0.80313(16) 0.21906(9) 0.0278(3) Uani 1 1 d . . . . .
H6 H 0.520455 0.905603 0.226952 0.033 Uiso 1 1 calc R U . . .
C7 C 0.65758(19) 0.70040(16) 0.27724(8) 0.0238(3) Uani 1 1 d . . . . .
C8 C 0.72190(19) 0.55124(16) 0.26332(9) 0.0251(3) Uani 1 1 d . . . . .
H8 H 0.791274 0.480540 0.301209 0.030 Uiso 1 1 calc R U . . .
C9 C 0.6860(2) 0.50486(16) 0.19508(9) 0.0262(3) Uani 1 1 d . . . . .
H9 H 0.729571 0.402480 0.187002 0.031 Uiso 1 1 calc R U . . .
C10 C 0.68392(19) 0.74822(16) 0.35548(8) 0.0239(3) Uani 1 1 d . . . . .
C11 C 0.3526(2) 0.40509(16) 0.16133(8) 0.0245(3) Uani 1 1 d . . . . .
C12 C 0.2371(2) 0.51211(16) 0.20953(9) 0.0253(3) Uani 1 1 d . . . . .
H12 H 0.196293 0.612565 0.186806 0.030 Uiso 1 1 calc R U . . .
C13 C 0.18130(19) 0.47428(16) 0.28971(9) 0.0242(3) Uani 1 1 d . . . . .
H13 H 0.105255 0.548782 0.322155 0.029 Uiso 1 1 calc R U . . .
C14 C 0.23675(19) 0.32639(15) 0.32304(8) 0.0225(3) Uani 1 1 d . . . . .
C15 C 0.3420(2) 0.21645(16) 0.27426(9) 0.0249(3) Uani 1 1 d . . . . .
H15 H 0.374220 0.114961 0.295953 0.030 Uiso 1 1 calc R U . . .
C16 C 0.3994(2) 0.25604(16) 0.19386(9) 0.0258(3) Uani 1 1 d . . . . .
H16 H 0.471076 0.181195 0.160712 0.031 Uiso 1 1 calc R U . . .
C17 C 0.20006(18) 0.28458(15) 0.41184(9) 0.0228(3) Uani 1 1 d . . . . .
C18 C 0.0684(2) -0.09827(17) 0.34399(9) 0.0285(3) Uani 1 1 d . . . . .
H18A H 0.148936 -0.036048 0.316702 0.034 Uiso 1 1 calc R U . . .
H18B H 0.022506 -0.136574 0.302103 0.034 Uiso 1 1 calc R U . . .
C19 C 0.1777(2) -0.22627(16) 0.39748(9) 0.0281(3) Uani 1 1 d . . . . .
H19A H 0.102469 -0.295682 0.419181 0.034 Uiso 1 1 calc R U . . .
H19B H 0.292592 -0.281454 0.366013 0.034 Uiso 1 1 calc R U . . .
C20 C 0.3038(2) -0.28489(16) 0.52700(10) 0.0288(3) Uani 1 1 d . . . . .
H20A H 0.418021 -0.353933 0.502373 0.035 Uiso 1 1 calc R U . . .
H20B H 0.213046 -0.341907 0.547712 0.035 Uiso 1 1 calc R U . . .
C21 C 0.3502(2) -0.22312(17) 0.59675(10) 0.0303(3) Uani 1 1 d . . . . .
H21A H 0.430832 -0.158042 0.574607 0.036 Uiso 1 1 calc R U . . .
H21B H 0.422853 -0.307004 0.631449 0.036 Uiso 1 1 calc R U . . .
C22 C -0.1835(2) 0.13508(17) 0.35082(9) 0.0293(3) Uani 1 1 d . . . . .
H22A H -0.225061 0.116082 0.301614 0.035 Uiso 1 1 calc R U . . .
H22B H -0.093702 0.194195 0.333851 0.035 Uiso 1 1 calc R U . . .
H2 H 0.194(4) 0.364(3) 0.5057(17) 0.073(8) Uiso 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 O1 2.4005(10) 2_556 ?
Cu1 O1 2.4005(10) . ?
Cu1 N1 2.0204(12) 2_556 ?
Cu1 N1 2.0204(12) . ?
Cu1 N2 2.0168(12) . ?
Cu1 N2 2.0169(12) 2_556 ?
O1 C17 1.2279(17) . ?
O2 C17 1.3012(18) . ?
O2 H2 0.85(3) . ?
O3 C10 1.2727(18) . ?
O4 C10 1.2463(18) . ?
N1 H1 1.0000 . ?
N1 C19 1.4799(18) . ?
N1 C20 1.4821(18) . ?
N2 H2A 1.0000 . ?
N2 C18 1.4837(19) . ?
N2 C22 1.4816(18) . ?
C1 H1A 0.9500 . ?
C1 C2 1.393(2) . ?
C1 C3 1.395(2) 2_665 ?
C2 C3 1.408(2) . ?
C2 C4 1.4930(19) . ?
C3 C11 1.490(2) . ?
C4 C5 1.395(2) . ?
C4 C9 1.398(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.396(2) . ?
C7 C8 1.393(2) . ?
C7 C10 1.5163(19) . ?
C8 H8 0.9500 . ?
C8 C9 1.382(2) . ?
C9 H9 0.9500 . ?
C11 C12 1.395(2) . ?
C11 C16 1.398(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.395(2) . ?
C14 C15 1.396(2) . ?
C14 C17 1.4956(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(2) . ?
C16 H16 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.511(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.519(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.521(2) 2_556 ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?

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 Cu1 O1 180.0 2_556 . ?
N1 Cu1 O1 95.75(4) . 2_556 ?
N1 Cu1 O1 84.25(4) . . ?
N1 Cu1 O1 84.25(4) 2_556 2_556 ?
N1 Cu1 O1 95.75(4) 2_556 . ?
N1 Cu1 N1 180.0 2_556 . ?
N2 Cu1 O1 86.45(4) 2_556 . ?
N2 Cu1 O1 93.55(4) 2_556 2_556 ?
N2 Cu1 O1 93.55(4) . . ?
N2 Cu1 O1 86.45(4) . 2_556 ?
N2 Cu1 N1 94.16(5) 2_556 . ?
N2 Cu1 N1 94.16(5) . 2_556 ?
N2 Cu1 N1 85.84(5) . . ?
N2 Cu1 N1 85.84(5) 2_556 2_556 ?
N2 Cu1 N2 180.00(7) . 2_556 ?
C17 O1 Cu1 149.43(10) . . ?
C17 O2 H2 115.4(18) . . ?
Cu1 N1 H1 106.7 . . ?
C19 N1 Cu1 107.21(9) . . ?
C19 N1 H1 106.7 . . ?
C19 N1 C20 111.21(11) . . ?
C20 N1 Cu1 117.67(9) . . ?
C20 N1 H1 106.7 . . ?
Cu1 N2 H2A 106.6 . . ?
C18 N2 Cu1 107.46(9) . . ?
C18 N2 H2A 106.6 . . ?
C22 N2 Cu1 117.13(9) . . ?
C22 N2 H2A 106.6 . . ?
C22 N2 C18 111.94(11) . . ?
C2 C1 H1A 119.0 . . ?
C2 C1 C3 122.00(14) . 2_665 ?
C3 C1 H1A 119.0 2_665 . ?
C1 C2 C3 118.89(13) . . ?
C1 C2 C4 120.30(13) . . ?
C3 C2 C4 120.75(13) . . ?
C1 C3 C2 119.11(13) 2_665 . ?
C1 C3 C11 120.71(13) 2_665 . ?
C2 C3 C11 120.14(13) . . ?
C5 C4 C2 121.40(13) . . ?
C5 C4 C9 118.32(13) . . ?
C9 C4 C2 120.25(13) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.77(13) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.65(13) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C10 121.05(13) . . ?
C8 C7 C6 118.53(13) . . ?
C8 C7 C10 120.38(13) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.83(13) . . ?
C9 C8 H8 119.6 . . ?
C4 C9 H9 119.6 . . ?
C8 C9 C4 120.80(13) . . ?
C8 C9 H9 119.6 . . ?
O3 C10 C7 115.13(12) . . ?
O4 C10 O3 126.11(13) . . ?
O4 C10 C7 118.77(13) . . ?
C12 C11 C3 119.88(13) . . ?
C12 C11 C16 118.74(13) . . ?
C16 C11 C3 121.29(13) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.01(13) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.87(13) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 119.81(13) . . ?
C13 C14 C17 121.11(13) . . ?
C15 C14 C17 118.86(12) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.77(13) . . ?
C16 C15 H15 120.1 . . ?
C11 C16 H16 119.7 . . ?
C15 C16 C11 120.56(13) . . ?
C15 C16 H16 119.7 . . ?
O1 C17 O2 124.92(14) . . ?
O1 C17 C14 121.55(13) . . ?
O2 C17 C14 113.48(12) . . ?
N2 C18 H18A 110.0 . . ?
N2 C18 H18B 110.0 . . ?
N2 C18 C19 108.42(11) . . ?
H18A C18 H18B 108.4 . . ?
C19 C18 H18A 110.0 . . ?
C19 C18 H18B 110.0 . . ?
N1 C19 C18 108.23(11) . . ?
N1 C19 H19A 110.1 . . ?
N1 C19 H19B 110.1 . . ?
C18 C19 H19A 110.1 . . ?
C18 C19 H19B 110.1 . . ?
H19A C19 H19B 108.4 . . ?
N1 C20 H20A 109.3 . . ?
N1 C20 H20B 109.3 . . ?
N1 C20 C21 111.68(12) . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
C20 C21 H21A 108.5 . . ?
C20 C21 H21B 108.5 . . ?
C20 C21 C22 115.28(12) . 2_556 ?
H21A C21 H21B 107.5 . . ?
C22 C21 H21A 108.5 2_556 . ?
C22 C21 H21B 108.5 2_556 . ?
N2 C22 C21 111.12(12) . 2_556 ?
N2 C22 H22A 109.4 . . ?
N2 C22 H22B 109.4 . . ?
C21 C22 H22A 109.4 2_556 . ?
C21 C22 H22B 109.4 2_556 . ?
H22A C22 H22B 108.0 . . ?

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
N1 H1 O4 1.00 2.15 3.0626(16) 151.2 1_545 yes
N2 H2A O4 1.00 2.12 3.0183(15) 148.4 1_445 yes
C19 H19A O3 0.99 2.58 3.3969(18) 139.6 1_445 yes
O2 H2 O3 0.85(3) 1.63(3) 2.4769(14) 168(3) 2_666 yes

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 C17 O2 76.3(2) . . . . ?
Cu1 O1 C17 C14 -106.41(19) . . . . ?
Cu1 N1 C19 C18 40.31(13) . . . . ?
Cu1 N1 C20 C21 -54.90(14) . . . . ?
Cu1 N2 C18 C19 38.78(13) . . . . ?
Cu1 N2 C22 C21 -57.22(14) . . . 2_556 ?
N1 C20 C21 C22 68.52(16) . . . 2_556 ?
N2 C18 C19 N1 -53.30(15) . . . . ?
C1 C2 C3 C1 0.6(2) . . . 2_665 ?
C1 C2 C3 C11 -177.05(13) . . . . ?
C1 C2 C4 C5 62.8(2) . . . . ?
C1 C2 C4 C9 -119.22(16) . . . . ?
C1 C3 C11 C12 -121.53(15) 2_665 . . . ?
C1 C3 C11 C16 62.0(2) 2_665 . . . ?
C2 C3 C11 C12 56.10(19) . . . . ?
C2 C3 C11 C16 -120.42(15) . . . . ?
C2 C4 C5 C6 174.70(14) . . . . ?
C2 C4 C9 C8 -175.90(13) . . . . ?
C3 C1 C2 C3 -0.6(2) 2_665 . . . ?
C3 C1 C2 C4 176.73(13) 2_665 . . . ?
C3 C2 C4 C5 -119.85(16) . . . . ?
C3 C2 C4 C9 58.10(19) . . . . ?
C3 C11 C12 C13 -171.58(13) . . . . ?
C3 C11 C16 C15 172.38(13) . . . . ?
C4 C2 C3 C1 -176.73(13) . . . 2_665 ?
C4 C2 C3 C11 5.6(2) . . . . ?
C4 C5 C6 C7 1.5(2) . . . . ?
C5 C4 C9 C8 2.1(2) . . . . ?
C5 C6 C7 C8 1.5(2) . . . . ?
C5 C6 C7 C10 -176.13(13) . . . . ?
C6 C7 C8 C9 -2.7(2) . . . . ?
C6 C7 C10 O3 -167.79(13) . . . . ?
C6 C7 C10 O4 12.4(2) . . . . ?
C7 C8 C9 C4 0.9(2) . . . . ?
C8 C7 C10 O3 14.65(19) . . . . ?
C8 C7 C10 O4 -165.11(13) . . . . ?
C9 C4 C5 C6 -3.3(2) . . . . ?
C10 C7 C8 C9 174.96(13) . . . . ?
C11 C12 C13 C14 -1.6(2) . . . . ?
C12 C11 C16 C15 -4.2(2) . . . . ?
C12 C13 C14 C15 -2.7(2) . . . . ?
C12 C13 C14 C17 171.84(13) . . . . ?
C13 C14 C15 C16 3.5(2) . . . . ?
C13 C14 C17 O1 154.98(14) . . . . ?
C13 C14 C17 O2 -27.42(18) . . . . ?
C14 C15 C16 C11 0.0(2) . . . . ?
C15 C14 C17 O1 -30.4(2) . . . . ?
C15 C14 C17 O2 147.15(13) . . . . ?
C16 C11 C12 C13 5.0(2) . . . . ?
C17 C14 C15 C16 -171.15(13) . . . . ?
C18 N2 C22 C21 178.04(12) . . . 2_556 ?
C19 N1 C20 C21 -179.08(12) . . . . ?
C20 N1 C19 C18 170.23(11) . . . . ?
C22 N2 C18 C19 168.73(11) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.068 -0.020 0.000 293.8 4.5 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_olex2_submission_original_sample_id ND1-Act_Cu
_olex2_submission_special_instructions 'No special instructions were received'
