# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_mo_SH_Saskia_2_1_1M_0m_a_sq
_database_code_depnum_ccdc_archive 'CCDC 1999766'
loop_
_audit_author_name
_audit_author_address
'Christoph Janiak'
;University of Duesseldorf
Germany
;
_audit_update_record             
;
2020-07-23 deposited with the CCDC.	2020-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H22 Cu N4 O4, C3 H7 N O'
_chemical_formula_sum            'C27 H29 Cu N5 O5'
_chemical_formula_weight         567.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

# start Validation Reply Form
_vrf_PLAT930_mo_SH_Saskia_2_1_1M_0m_a_sq 
;
PROBLEM: FCF-based   Twin Law ( 0 0 1)[ 1 0 2] Est.d BASF       0.19 Check 
RESPONSE: BASF refines to very low values and collides with SQUEEZE procedure. 
The therefore very low amount of twinning was ignored.
;
# end Validation Reply Form

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.0436(8)
_cell_length_b                   17.2646(14)
_cell_length_c                   17.3187(14)
_cell_angle_alpha                90
_cell_angle_beta                 105.201(4)
_cell_angle_gamma                90
_cell_volume                     2898.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    9759
_cell_measurement_theta_min      2.359
_cell_measurement_theta_max      27.402

_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             1180
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.796
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9039
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'

_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans, φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39626
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.696
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6386
_reflns_number_gt                5474
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick 2015a)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND 4.3.1 (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2015b)'

_refine_special_details          
;Refinement of F² against ALL reflections. The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger. Refined as a 2-component twin.,SQUEEZE
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0302P)²+44.6080P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6386
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0909
_refine_ls_wR_factor_ref         0.2380
_refine_ls_wR_factor_gt          0.2338
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_restrained_S_all      1.181
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.24500(7) 0.49511(4) 0.52068(4) 0.0107(2) Uani 1 1 d . . . . .
O1 O 0.2978(4) 0.4012(2) 0.5862(2) 0.0116(8) Uani 1 1 d . . . . .
N1 N 0.7839(5) 0.0370(3) 0.8633(3) 0.0132(10) Uani 1 1 d . . . . .
H1 H 0.847(8) -0.004(5) 0.883(4) 0.020 Uiso 1 1 d . U . . .
C1 C 0.7510(6) 0.0810(3) 0.7976(4) 0.0138(12) Uani 1 1 d . . . . .
N2 N 0.7275(5) 0.0652(3) 0.9209(3) 0.0114(10) Uani 1 1 d . . . . .
O2 O 0.5038(4) 0.4396(2) 0.5767(3) 0.0145(9) Uani 1 1 d . . . . .
C2 C 0.6662(6) 0.1403(3) 0.8108(3) 0.0128(11) Uani 1 1 d . . . . .
O3 O 0.1833(5) 0.5898(2) 0.4606(2) 0.0146(9) Uani 1 1 d . . . . .
N3 N -0.2528(6) 0.9672(3) 0.1842(3) 0.0165(11) Uani 1 1 d . . . . .
H3 H -0.316(9) 0.999(5) 0.175(5) 0.025 Uiso 1 1 d . U . . .
C3 C 0.6527(6) 0.1269(3) 0.8897(3) 0.0118(11) Uani 1 1 d . . . . .
N4 N -0.2091(5) 0.9426(3) 0.1201(3) 0.0121(10) Uani 1 1 d . . . . .
O4 O -0.0166(5) 0.5320(3) 0.4022(3) 0.0223(10) Uani 1 1 d . . . . .
C4 C 0.7974(7) 0.0587(4) 0.7254(4) 0.0198(13) Uani 1 1 d . . . . .
H4A H 0.738938 0.016733 0.697005 0.030 Uiso 1 1 calc R U . . .
H4B H 0.893507 0.041160 0.742026 0.030 Uiso 1 1 calc R U . . .
H4C H 0.790195 0.103575 0.689923 0.030 Uiso 1 1 calc R U . . .
N5 N 0.0665(10) 0.6381(5) 0.0357(5) 0.049(2) Uani 1 1 d . . . . .
C5 C 0.5679(7) 0.1681(4) 0.9356(4) 0.0193(13) Uani 1 1 d . . . . .
H5A H 0.551276 0.221424 0.916044 0.029 Uiso 1 1 calc R U . . .
H5B H 0.617144 0.168687 0.992513 0.029 Uiso 1 1 calc R U . . .
H5C H 0.479484 0.141303 0.928472 0.029 Uiso 1 1 calc R U . . .
O5 O -0.0466(15) 0.5671(7) 0.1080(6) 0.119(5) Uani 1 1 d . . . . .
C6 C 0.6058(6) 0.2050(3) 0.7578(3) 0.0141(12) Uani 1 1 d . . . . .
C7 C 0.6855(6) 0.2474(4) 0.7172(4) 0.0172(13) Uani 1 1 d . . . . .
H7 H 0.779617 0.234120 0.723677 0.021 Uiso 1 1 calc R U . . .
C8 C 0.6278(6) 0.3086(4) 0.6676(4) 0.0174(13) Uani 1 1 d . . . . .
H8 H 0.683251 0.337283 0.640950 0.021 Uiso 1 1 calc R U . . .
C9 C 0.4910(6) 0.3282(3) 0.6565(4) 0.0132(12) Uani 1 1 d . . . . .
C10 C 0.4097(6) 0.2866(4) 0.6961(4) 0.0181(13) Uani 1 1 d . . . . .
H10 H 0.315198 0.299616 0.688515 0.022 Uiso 1 1 calc R U . . .
C19 C -0.0980(7) 0.7179(4) 0.2355(3) 0.0159(12) Uani 1 1 d . . . . .
H19 H -0.143830 0.712528 0.180356 0.019 Uiso 1 1 calc R U . . .
C18 C -0.0798(6) 0.7919(3) 0.2704(3) 0.0118(11) Uani 1 1 d . . . . .
C17 C -0.0703(7) 0.8348(4) 0.0893(3) 0.0167(12) Uani 1 1 d . . . . .
H17A H -0.128202 0.791107 0.064642 0.025 Uiso 1 1 calc R U . . .
H17B H 0.019559 0.815576 0.120361 0.025 Uiso 1 1 calc R U . . .
H17C H -0.057231 0.869938 0.047405 0.025 Uiso 1 1 calc R U . . .
C16 C -0.2567(8) 0.9338(4) 0.3215(4) 0.0281(16) Uani 1 1 d . . . . .
H16A H -0.352121 0.952437 0.308317 0.042 Uiso 1 1 calc R U . . .
H16B H -0.195759 0.972777 0.353779 0.042 Uiso 1 1 calc R U . . .
H16C H -0.249665 0.885390 0.351892 0.042 Uiso 1 1 calc R U . . .
C15 C -0.1388(6) 0.8773(3) 0.1431(3) 0.0109(11) Uani 1 1 d . . . . .
C14 C -0.1400(6) 0.8603(3) 0.2238(3) 0.0114(11) Uani 1 1 d . . . . .
C13 C -0.2146(6) 0.9197(3) 0.2461(4) 0.0142(12) Uani 1 1 d . . . . .
C11 C 0.4678(7) 0.2260(4) 0.7469(4) 0.0188(13) Uani 1 1 d . . . . .
H11 H 0.412653 0.198513 0.774618 0.023 Uiso 1 1 calc R U . . .
C20 C -0.0498(6) 0.6527(3) 0.2808(4) 0.0142(12) Uani 1 1 d . . . . .
H20 H -0.064466 0.602952 0.256687 0.017 Uiso 1 1 calc R U . . .
C21 C 0.0199(6) 0.6596(3) 0.3614(4) 0.0130(11) Uani 1 1 d . . . . .
C22 C 0.0436(6) 0.7326(4) 0.3961(4) 0.0143(12) Uani 1 1 d . . . . .
H22 H 0.095185 0.737758 0.450299 0.017 Uiso 1 1 calc R U . . .
C23 C -0.0078(6) 0.7980(4) 0.3517(4) 0.0149(12) Uani 1 1 d . . . . .
H23 H 0.005626 0.847532 0.376472 0.018 Uiso 1 1 calc R U . . .
C24 C 0.0635(6) 0.5879(3) 0.4109(3) 0.0125(11) Uani 1 1 d . . . . .
C25 C 0.0520(15) 0.6104(7) 0.1046(6) 0.064(3) Uani 1 1 d . . . . .
H25 H 0.118460 0.623713 0.152806 0.077 Uiso 1 1 calc R U . . .
C26 C -0.0229(18) 0.6180(10) -0.0390(8) 0.097(5) Uani 1 1 d . . . . .
H26A H -0.035927 0.662923 -0.074849 0.146 Uiso 1 1 calc R U . . .
H26B H -0.112239 0.601854 -0.031602 0.146 Uiso 1 1 calc R U . . .
H26C H 0.017439 0.575302 -0.062591 0.146 Uiso 1 1 calc R U . . .
C27 C 0.1775(17) 0.6889(11) 0.0333(10) 0.107(6) Uani 1 1 d . . . . .
H27A H 0.245458 0.660928 0.012358 0.160 Uiso 1 1 calc R U . . .
H27B H 0.221450 0.707468 0.087483 0.160 Uiso 1 1 calc R U . . .
H27C H 0.141822 0.733063 -0.001448 0.160 Uiso 1 1 calc R U . . .
C12 C 0.4271(6) 0.3946(3) 0.6021(3) 0.0093(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O3 1.949(4) . ?
Cu1 O1 1.970(4) . ?
Cu1 N4 1.980(5) 4_676 ?
Cu1 N2 1.986(5) 4_565 ?
O1 C12 1.260(7) . ?
N1 C1 1.336(8) . ?
N1 N2 1.359(7) . ?
N1 H1 0.95(8) . ?
C1 C2 1.388(8) . ?
C1 C4 1.495(8) . ?
N2 C3 1.334(7) . ?
O2 C12 1.253(7) . ?
C2 C3 1.426(8) . ?
C2 C6 1.473(8) . ?
O3 C24 1.284(7) . ?
N3 C13 1.324(8) . ?
N3 N4 1.364(7) . ?
N3 H3 0.82(9) . ?
C3 C5 1.490(8) . ?
N4 C15 1.336(7) . ?
O4 C24 1.241(7) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N5 C25 1.329(13) . ?
N5 C26 1.411(14) . ?
N5 C27 1.428(15) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
O5 C25 1.254(15) . ?
C6 C11 1.396(9) . ?
C6 C7 1.402(9) . ?
C7 C8 1.390(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.378(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.396(8) . ?
C9 C12 1.515(8) . ?
C10 C11 1.393(8) . ?
C10 H10 0.9500 . ?
C19 C20 1.384(8) . ?
C19 C18 1.405(8) . ?
C19 H19 0.9500 . ?
C18 C23 1.407(8) . ?
C18 C14 1.468(8) . ?
C17 C15 1.488(8) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C16 C13 1.493(9) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C15 C14 1.430(8) . ?
C14 C13 1.384(8) . ?
C11 H11 0.9500 . ?
C20 C21 1.393(8) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(8) . ?
C21 C24 1.504(8) . ?
C22 C23 1.387(8) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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
O3 Cu1 O1 175.74(19) . . ?
O3 Cu1 N4 88.73(19) . 4_676 ?
O1 Cu1 N4 88.82(18) . 4_676 ?
O3 Cu1 N2 91.84(19) . 4_565 ?
O1 Cu1 N2 91.10(18) . 4_565 ?
N4 Cu1 N2 171.6(2) 4_676 4_565 ?
C12 O1 Cu1 107.8(4) . . ?
C1 N1 N2 111.3(5) . . ?
C1 N1 H1 136(5) . . ?
N2 N1 H1 112(5) . . ?
N1 C1 C2 107.7(5) . . ?
N1 C1 C4 120.3(5) . . ?
C2 C1 C4 131.8(6) . . ?
C3 N2 N1 106.7(5) . . ?
C3 N2 Cu1 133.1(4) . 4_666 ?
N1 N2 Cu1 119.5(4) . 4_666 ?
C1 C2 C3 104.8(5) . . ?
C1 C2 C6 128.8(5) . . ?
C3 C2 C6 126.3(5) . . ?
C24 O3 Cu1 116.6(4) . . ?
C13 N3 N4 112.3(5) . . ?
C13 N3 H3 128(6) . . ?
N4 N3 H3 116(6) . . ?
N2 C3 C2 109.4(5) . . ?
N2 C3 C5 120.4(5) . . ?
C2 C3 C5 130.2(5) . . ?
C15 N4 N3 106.1(5) . . ?
C15 N4 Cu1 134.6(4) . 4_575 ?
N3 N4 Cu1 119.2(4) . 4_575 ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C25 N5 C26 122.9(11) . . ?
C25 N5 C27 121.1(11) . . ?
C26 N5 C27 116.0(11) . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C6 C7 118.3(5) . . ?
C11 C6 C2 120.9(5) . . ?
C7 C6 C2 120.8(6) . . ?
C8 C7 C6 120.4(6) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C7 120.8(6) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 119.7(5) . . ?
C8 C9 C12 121.1(5) . . ?
C10 C9 C12 119.2(5) . . ?
C11 C10 C9 119.6(6) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C20 C19 C18 120.6(5) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C18 C23 118.2(5) . . ?
C19 C18 C14 120.4(5) . . ?
C23 C18 C14 121.3(5) . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N4 C15 C14 109.0(5) . . ?
N4 C15 C17 121.6(5) . . ?
C14 C15 C17 129.4(5) . . ?
C13 C14 C15 105.4(5) . . ?
C13 C14 C18 128.1(5) . . ?
C15 C14 C18 126.5(5) . . ?
N3 C13 C14 107.2(5) . . ?
N3 C13 C16 121.2(6) . . ?
C14 C13 C16 131.6(6) . . ?
C10 C11 C6 121.1(6) . . ?
C10 C11 H11 119.4 . . ?
C6 C11 H11 119.4 . . ?
C19 C20 C21 120.5(6) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 119.6(5) . . ?
C22 C21 C24 120.6(5) . . ?
C20 C21 C24 119.8(5) . . ?
C23 C22 C21 120.1(5) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C18 120.8(6) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?
O4 C24 O3 124.4(5) . . ?
O4 C24 C21 119.2(5) . . ?
O3 C24 C21 116.3(5) . . ?
O5 C25 N5 122.0(11) . . ?
O5 C25 H25 119.0 . . ?
N5 C25 H25 119.0 . . ?
N5 C26 H26A 109.5 . . ?
N5 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N5 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N5 C27 H27A 109.5 . . ?
N5 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N5 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O2 C12 O1 124.2(5) . . ?
O2 C12 C9 119.2(5) . . ?
O1 C12 C9 116.7(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.95(8) 1.77(8) 2.700(7) 165(7) 2_646
N3 H3 O4 0.82(9) 1.94(8) 2.653(7) 145(8) 2_455
C5 H5B O1 0.98 2.42 3.226(7) 139.7 4_666
C17 H17C O2 0.98 2.64 3.603(8) 168.6 2
C26 H26C O5 0.98 2.62 3.54(2) 157.1 3_565

_refine_diff_density_max         2.095
_refine_diff_density_min         -1.152
_refine_diff_density_rms         0.167



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: N,N-dimethylformamide/water'
####################################################################### 
# 
# 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_mo_HeeringCHD007H2O_0m
_database_code_depnum_ccdc_archive 'CCDC 1999768'
loop_
_audit_author_name
_audit_author_address
'Christoph Janiak'
;University of Duesseldorf
Germany
;
_audit_update_record             
;
2020-07-23 deposited with the CCDC.	2020-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H22 Cu N4 O4, 8.968(H2 O)'
_chemical_formula_sum            'C24 H39.94 Cu N4 O12.96'
_chemical_formula_weight         655.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/4, x+3/4, z+3/4'
'y+1/4, -x+1/4, z+1/4'
'-x, -y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-y+3/4, x+5/4, z+5/4'
'y+3/4, -x+3/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'-x, -y, -z'
'y-1/4, -x-3/4, -z-3/4'
'-y-1/4, x-1/4, -z-1/4'
'x, y-1/2, -z'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/4, -x-1/4, -z-1/4'
'-y+1/4, x+1/4, -z+1/4'
'x+1/2, y, -z+1/2'

_cell_length_a                   23.2432(12)
_cell_length_b                   23.2432(12)
_cell_length_c                   11.9130(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6436.0(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    9155
_cell_measurement_theta_min      2.478
_cell_measurement_theta_max      26.406

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             2757
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.137
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.059
_exptl_absorpt_coefficient_mu    0.743
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6226
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans, φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48071
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_av_R_equivalents  0.1230
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.752
_diffrn_reflns_theta_max         26.473
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3301
_reflns_number_gt                3060
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick 2015a)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND 4.3.1 (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2015b)'

_refine_special_details          
;
 Refinement of F² against ALL reflections. The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0458P)²+15.6649P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3301
_refine_ls_number_parameters     236
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1103
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.136
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.000000 0.500000 0.000000 0.01314(13) Uani 1 2 d S . P . .
O1 O 0.20773(7) 0.69874(6) 0.65079(12) 0.0178(3) Uani 1 1 d . . . . .
O2 O 0.29265(7) 0.69381(7) 0.56713(14) 0.0262(4) Uani 1 1 d . . . . .
N1 N 0.10807(8) 0.47632(8) 0.10782(15) 0.0183(4) Uani 1 1 d . . . . .
H1 H 0.1055(13) 0.4451(13) 0.071(3) 0.027 Uiso 1 1 d . U . . .
N2 N 0.06734(8) 0.51754(8) 0.09657(15) 0.0175(4) Uani 1 1 d . . . . .
C1 C 0.14704(10) 0.48956(9) 0.18672(18) 0.0191(4) Uani 1 1 d . . . . .
C2 C 0.13144(10) 0.54291(10) 0.22880(18) 0.0190(4) Uani 1 1 d . . . . .
C3 C 0.08151(9) 0.55905(9) 0.16911(18) 0.0186(4) Uani 1 1 d . . . . .
C4 C 0.19554(11) 0.45018(11) 0.2125(2) 0.0280(5) Uani 1 1 d . . . . .
H4C H 0.180654 0.411293 0.225462 0.042 Uiso 1 1 calc R U . . .
H4D H 0.215587 0.463660 0.279882 0.042 Uiso 1 1 calc R U . . .
H4E H 0.222392 0.449570 0.149062 0.042 Uiso 1 1 calc R U . . .
C5 C 0.04971(11) 0.61458(10) 0.1741(2) 0.0280(5) Uani 1 1 d . . . . .
H5C H 0.029736 0.621029 0.102747 0.042 Uiso 1 1 calc R U . . .
H5D H 0.076908 0.646049 0.187554 0.042 Uiso 1 1 calc R U . . .
H5E H 0.021548 0.613216 0.235255 0.042 Uiso 1 1 calc R U . . .
C6 C 0.16073(10) 0.57655(9) 0.31770(18) 0.0201(4) Uani 1 1 d . . . . .
C7 C 0.12841(10) 0.60040(10) 0.40454(19) 0.0217(5) Uani 1 1 d . . . . .
H7 H 0.088059 0.594014 0.406885 0.026 Uiso 1 1 calc R U . . .
C8 C 0.15417(10) 0.63326(10) 0.48750(18) 0.0204(5) Uani 1 1 d . . . . .
H8 H 0.131388 0.649314 0.545837 0.025 Uiso 1 1 calc R U . . .
C9 C 0.21330(10) 0.64286(9) 0.48579(17) 0.0184(4) Uani 1 1 d . . . . .
C10 C 0.24613(10) 0.61861(11) 0.4001(2) 0.0259(5) Uani 1 1 d . . . . .
H10 H 0.286542 0.624655 0.398435 0.031 Uiso 1 1 calc R U . . .
C11 C 0.22023(10) 0.58576(11) 0.31738(19) 0.0252(5) Uani 1 1 d . . . . .
H11 H 0.243129 0.569276 0.259686 0.030 Uiso 1 1 calc R U . . .
C12 C 0.24062(9) 0.68067(9) 0.57305(18) 0.0180(4) Uani 1 1 d . . . . .
O3 O -0.10831(8) 0.35084(9) 0.19180(19) 0.0368(7) Uani 0.963(7) 1 d D . P A 1
H3A H -0.0943(16) 0.3341(13) 0.138(2) 0.055 Uiso 0.963(7) 1 d D U P A 1
H3B H -0.0924(15) 0.3824(8) 0.191(3) 0.055 Uiso 0.963(7) 1 d D U P A 1
O6 O 0.03679(11) 0.38944(11) 0.2558(2) 0.0416(9) Uani 0.858(8) 1 d D . P B 2
H6A H 0.0555(17) 0.3775(19) 0.203(2) 0.062 Uiso 0.858(8) 1 d D U P B 2
H6B H 0.0132(15) 0.4121(16) 0.231(3) 0.062 Uiso 0.858(8) 1 d D U P B 2
O7 O 0.5157(2) 0.44025(17) 0.0159(3) 0.0817(15) Uani 0.903(10) 1 d D . P C 3
H7A H 0.512(3) 0.4752(7) 0.008(5) 0.123 Uiso 0.903(10) 1 d D U P C 3
H7B H 0.526(3) 0.436(3) 0.082(2) 0.123 Uiso 0.903(10) 1 d D U P C 3
O5 O 0.00131(10) 0.67265(11) 0.42824(19) 0.0374(8) Uani 0.863(8) 1 d D . P D 4
H5A H 0.012(2) 0.6909(14) 0.483(2) 0.056 Uiso 0.863(8) 1 d D U P D 4
H5B H -0.0067(19) 0.6404(8) 0.451(3) 0.056 Uiso 0.863(8) 1 d D U P D 4
O4 O -0.02768(9) 0.30310(10) 0.34594(19) 0.0354(8) Uani 0.897(8) 1 d D . P E 5
H4A H -0.0051(14) 0.3274(11) 0.322(3) 0.053 Uiso 0.897(8) 1 d D U P E 5
H4B H -0.0160(16) 0.2726(8) 0.321(3) 0.053 Uiso 0.897(8) 1 d D U P E 5


_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 1.9446(14) 14_466 ?
Cu1 O1 1.9446(14) 6_543 ?
Cu1 N2 1.9849(17) 9_565 ?
Cu1 N2 1.9850(17) . ?
O1 C12 1.272(3) . ?
O2 C12 1.249(3) . ?
N1 C1 1.341(3) . ?
N1 N2 1.354(3) . ?
N1 H1 0.85(3) . ?
N2 C3 1.336(3) . ?
C1 C2 1.386(3) . ?
C1 C4 1.484(3) . ?
C2 C3 1.412(3) . ?
C2 C6 1.482(3) . ?
C3 C5 1.488(3) . ?
C4 H4C 0.9800 . ?
C4 H4D 0.9800 . ?
C4 H4E 0.9800 . ?
C5 H5C 0.9800 . ?
C5 H5D 0.9800 . ?
C5 H5E 0.9800 . ?
C6 C7 1.393(3) . ?
C6 C11 1.400(3) . ?
C7 C8 1.385(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.393(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(3) . ?
C9 C12 1.502(3) . ?
C10 C11 1.384(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
O3 H3A 0.812(10) . ?
O3 H3B 0.822(10) . ?
O6 H6A 0.815(10) . ?
O6 H6B 0.815(10) . ?
O7 H7A 0.821(10) . ?
O7 H7B 0.824(10) . ?
O5 H5A 0.816(10) . ?
O5 H5B 0.818(10) . ?
O4 H4A 0.822(10) . ?
O4 H4B 0.814(10) . ?

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 180.00(8) 14_466 6_543 ?
O1 Cu1 N2 88.45(7) 14_466 9_565 ?
O1 Cu1 N2 91.55(7) 6_543 9_565 ?
O1 Cu1 N2 91.55(7) 14_466 . ?
O1 Cu1 N2 88.45(7) 6_543 . ?
N2 Cu1 N2 180.0 9_565 . ?
C12 O1 Cu1 109.95(13) . 7_455 ?
C1 N1 N2 112.29(18) . . ?
C1 N1 H1 127(2) . . ?
N2 N1 H1 120(2) . . ?
C3 N2 N1 105.95(17) . . ?
C3 N2 Cu1 135.84(15) . . ?
N1 N2 Cu1 117.61(13) . . ?
N1 C1 C2 106.39(19) . . ?
N1 C1 C4 121.1(2) . . ?
C2 C1 C4 132.5(2) . . ?
C1 C2 C3 105.71(18) . . ?
C1 C2 C6 127.6(2) . . ?
C3 C2 C6 126.7(2) . . ?
N2 C3 C2 109.65(19) . . ?
N2 C3 C5 122.0(2) . . ?
C2 C3 C5 128.22(19) . . ?
C1 C4 H4C 109.5 . . ?
C1 C4 H4D 109.5 . . ?
H4C C4 H4D 109.5 . . ?
C1 C4 H4E 109.5 . . ?
H4C C4 H4E 109.5 . . ?
H4D C4 H4E 109.5 . . ?
C3 C5 H5C 109.5 . . ?
C3 C5 H5D 109.5 . . ?
H5C C5 H5D 109.5 . . ?
C3 C5 H5E 109.5 . . ?
H5C C5 H5E 109.5 . . ?
H5D C5 H5E 109.5 . . ?
C7 C6 C11 118.3(2) . . ?
C7 C6 C2 119.5(2) . . ?
C11 C6 C2 122.2(2) . . ?
C8 C7 C6 121.1(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 120.3(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 119.09(19) . . ?
C8 C9 C12 120.06(19) . . ?
C10 C9 C12 120.8(2) . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C6 120.8(2) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?
O2 C12 O1 122.82(19) . . ?
O2 C12 C9 120.9(2) . . ?
O1 C12 C9 116.30(19) . . ?
H3A O3 H3B 103(2) . . ?
H6A O6 H6B 107(2) . . ?
H7A O7 H7B 104(3) . . ?
H5A O5 H5B 106(2) . . ?
H4A O4 H4B 105(2) . . ?

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
C1 N1 N2 C3 1.3(2) . . . . ?
C1 N1 N2 Cu1 -171.16(15) . . . . ?
N2 N1 C1 C2 -0.8(3) . . . . ?
N2 N1 C1 C4 -179.9(2) . . . . ?
N1 C1 C2 C3 -0.1(2) . . . . ?
C4 C1 C2 C3 178.9(2) . . . . ?
N1 C1 C2 C6 -179.9(2) . . . . ?
C4 C1 C2 C6 -0.9(4) . . . . ?
N1 N2 C3 C2 -1.3(2) . . . . ?
Cu1 N2 C3 C2 169.10(17) . . . . ?
N1 N2 C3 C5 174.3(2) . . . . ?
Cu1 N2 C3 C5 -15.3(4) . . . . ?
C1 C2 C3 N2 0.9(3) . . . . ?
C6 C2 C3 N2 -179.2(2) . . . . ?
C1 C2 C3 C5 -174.4(2) . . . . ?
C6 C2 C3 C5 5.5(4) . . . . ?
C1 C2 C6 C7 -132.4(3) . . . . ?
C3 C2 C6 C7 47.8(3) . . . . ?
C1 C2 C6 C11 48.1(4) . . . . ?
C3 C2 C6 C11 -131.8(3) . . . . ?
C11 C6 C7 C8 1.1(4) . . . . ?
C2 C6 C7 C8 -178.4(2) . . . . ?
C6 C7 C8 C9 -0.3(4) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C7 C8 C9 C12 177.3(2) . . . . ?
C8 C9 C10 C11 0.5(4) . . . . ?
C12 C9 C10 C11 -177.3(2) . . . . ?
C9 C10 C11 C6 0.4(4) . . . . ?
C7 C6 C11 C10 -1.2(4) . . . . ?
C2 C6 C11 C10 178.4(2) . . . . ?
Cu1 O1 C12 O2 2.0(3) 7_455 . . . ?
Cu1 O1 C12 C9 -176.93(14) 7_455 . . . ?
C8 C9 C12 O2 -173.7(2) . . . . ?
C10 C9 C12 O2 4.1(3) . . . . ?
C8 C9 C12 O1 5.3(3) . . . . ?
C10 C9 C12 O1 -176.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.85(3) 2.41(3) 2.831(2) 111(2) 6_543
N1 H1 O3 0.85(3) 2.03(3) 2.811(3) 153(3) 10_566
O3 H3B O2 0.822(10) 1.936(11) 2.758(3) 178(4) 14_466
O6 H6B O2 0.815(10) 2.009(14) 2.814(3) 169(5) 14_466
O7 H7A O7 0.821(10) 2.09(2) 2.897(8) 168(8) 9_665
O4 H4B O4 0.814(10) 2.05(2) 2.784(4) 150(4) 4

_refine_diff_density_max         0.705
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.077


_exptl_crystal_recrystallization_method 
'solvent exchange from the methanol-containing structure'
####################################################################### 
# 
# 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_SH_Saskia_5_2M_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 1999767'
loop_
_audit_author_name
_audit_author_address
'Christoph Janiak'
;University of Duesseldorf
Germany
;
_audit_update_record             
;
2020-07-23 deposited with the CCDC.	2020-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H22 Cu N4 O4, 2(C2 H3 N)'
_chemical_formula_sum            'C28 H28 Cu N6 O4'
_chemical_formula_weight         576.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.7946(10)
_cell_length_b                   19.5794(17)
_cell_length_c                   14.8975(14)
_cell_angle_alpha                90
_cell_angle_beta                 103.587(5)
_cell_angle_gamma                90
_cell_volume                     2777.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      2.379
_cell_measurement_theta_max      33.384

_exptl_crystal_description       block
_exptl_crystal_colour            'clear violet'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             1196
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.831
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9549
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans, φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            80053
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.749
_diffrn_reflns_theta_max         33.143
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10577
_reflns_number_gt                8382
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick 2015a)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND 4.3.1 (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2015b)'

_refine_special_details          
;
 Refinement of F² against ALL reflections. The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0582P)²+1.5308P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10577
_refine_ls_number_parameters     367
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.1022
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.500000 0.500000 0.01060(5) Uani 1 2 d S . P . .
O1 O 0.54165(9) 0.57122(4) 0.59429(6) 0.01397(15) Uani 1 1 d . . . . .
O2 O 0.31897(10) 0.54780(4) 0.59270(6) 0.01715(16) Uani 1 1 d . . . . .
N1 N 0.43843(11) 0.92938(5) 0.90199(7) 0.01318(17) Uani 1 1 d . . . . .
N2 N 0.32241(11) 0.94150(5) 0.83360(7) 0.01480(18) Uani 1 1 d . . . . .
H2 H 0.272(2) 0.9778(10) 0.8343(13) 0.022 Uiso 1 1 d . U . . .
C1 C 0.42575(12) 0.58460(5) 0.61625(8) 0.01285(19) Uani 1 1 d . . . . .
C2 C 0.42085(12) 0.64909(5) 0.66925(8) 0.01296(19) Uani 1 1 d . . . . .
C3 C 0.54092(12) 0.68866(6) 0.69953(9) 0.0156(2) Uani 1 1 d . . . . .
H3 H 0.628138 0.673629 0.689143 0.019 Uiso 1 1 calc R U . . .
C4 C 0.53362(13) 0.75007(6) 0.74490(9) 0.0165(2) Uani 1 1 d . . . . .
H4A H 0.616409 0.776389 0.766125 0.020 Uiso 1 1 calc R U . . .
C5 C 0.40591(12) 0.77362(6) 0.75969(8) 0.01391(19) Uani 1 1 d . . . . .
C6 C 0.28638(13) 0.73285(6) 0.73039(9) 0.0170(2) Uani 1 1 d . . . . .
H6 H 0.199185 0.747492 0.741233 0.020 Uiso 1 1 calc R U . . .
C7 C 0.29382(13) 0.67119(6) 0.68559(9) 0.0164(2) Uani 1 1 d . . . . .
H7 H 0.211868 0.644013 0.666045 0.020 Uiso 1 1 calc R U . . .
C8 C 0.39625(12) 0.84017(5) 0.80382(8) 0.01358(19) Uani 1 1 d . . . . .
C9 C 0.48637(12) 0.86799(5) 0.88407(8) 0.01340(19) Uani 1 1 d . . . . .
C10 C 0.29284(12) 0.88941(6) 0.77388(8) 0.01424(19) Uani 1 1 d . . . . .
C11 C 0.61770(13) 0.83881(6) 0.94337(9) 0.0181(2) Uani 1 1 d . . . . .
H11A H 0.699191 0.863240 0.931785 0.027 Uiso 1 1 calc R U . . .
H11B H 0.624478 0.790307 0.928745 0.027 Uiso 1 1 calc R U . . .
H11C H 0.615660 0.843717 1.008504 0.027 Uiso 1 1 calc R U . . .
C12 C 0.17274(14) 0.89333(7) 0.69126(9) 0.0204(2) Uani 1 1 d . . . . .
H12A H 0.208601 0.893879 0.635142 0.031 Uiso 1 1 calc R U . . .
H12B H 0.119028 0.935159 0.694242 0.031 Uiso 1 1 calc R U . . .
H12C H 0.111670 0.853533 0.690104 0.031 Uiso 1 1 calc R U . . .
Cu2 Cu 1.000000 0.500000 0.500000 0.01386(5) Uani 1 2 d S . P . .
O3 O 0.97404(11) 0.57711(4) 0.57575(6) 0.02099(19) Uani 1 1 d . U . . .
O4 O 0.88677(10) 0.53276(5) 0.68957(7) 0.02124(18) Uani 1 1 d . . . . .
N3 N 0.93232(11) 0.93858(5) 0.89500(7) 0.01474(18) Uani 1 1 d . . . . .
N4 N 0.82126(12) 0.95427(5) 0.82488(7) 0.01642(18) Uani 1 1 d . . . . .
H4 H 0.773(2) 0.9886(10) 0.8303(14) 0.025 Uiso 1 1 d . U . . .
C13 C 0.92631(12) 0.58082(5) 0.64825(8) 0.01419(19) Uani 1 1 d . U . . .
C14 C 0.91977(12) 0.65191(5) 0.68484(8) 0.01312(19) Uani 1 1 d . . . . .
C15 C 0.92876(13) 0.66145(6) 0.77886(8) 0.0165(2) Uani 1 1 d . . . . .
H15 H 0.941720 0.623240 0.819276 0.020 Uiso 1 1 calc R U . . .
C16 C 0.91882(13) 0.72656(6) 0.81352(8) 0.0168(2) Uani 1 1 d . . . . .
H16 H 0.926588 0.732567 0.877799 0.020 Uiso 1 1 calc R U . . .
C17 C 0.89753(12) 0.78349(5) 0.75512(8) 0.01310(19) Uani 1 1 d . . . . .
C18 C 0.88627(12) 0.77331(6) 0.66064(8) 0.01419(19) Uani 1 1 d . . . . .
H18 H 0.869787 0.811213 0.619700 0.017 Uiso 1 1 calc R U . . .
C19 C 0.89898(12) 0.70828(6) 0.62622(8) 0.01404(19) Uani 1 1 d . . . . .
H19 H 0.893448 0.702224 0.562199 0.017 Uiso 1 1 calc R U . . .
C20 C 0.88733(12) 0.85155(5) 0.79443(8) 0.01375(19) Uani 1 1 d . . . . .
C21 C 0.97512(12) 0.87655(6) 0.87743(8) 0.01365(19) Uani 1 1 d . . . . .
C22 C 0.79004(13) 0.90329(6) 0.76288(8) 0.0156(2) Uani 1 1 d . . . . .
C23 C 1.10311(13) 0.84503(6) 0.93722(9) 0.0179(2) Uani 1 1 d . . . . .
H23A H 1.075909 0.815534 0.983233 0.027 Uiso 1 1 calc R U . . .
H23B H 1.165957 0.881061 0.968658 0.027 Uiso 1 1 calc R U . . .
H23C H 1.151637 0.817782 0.899071 0.027 Uiso 1 1 calc R U . . .
C24 C 0.66901(15) 0.90905(7) 0.68094(9) 0.0224(2) Uani 1 1 d . . . . .
H24A H 0.584034 0.921113 0.701379 0.034 Uiso 1 1 calc R U . . .
H24B H 0.654774 0.865244 0.648239 0.034 Uiso 1 1 calc R U . . .
H24C H 0.688775 0.944568 0.639396 0.034 Uiso 1 1 calc R U . . .
N6 N 0.7117(3) 0.84346(11) 0.45762(13) 0.0639(6) Uani 1 1 d . . . . .
C27 C 0.6760(2) 0.88980(10) 0.41334(12) 0.0409(4) Uani 1 1 d . . . . .
C28 C 0.6313(3) 0.94878(10) 0.35654(16) 0.0564(6) Uani 1 1 d . . . . .
H28A H 0.676992 0.948874 0.304655 0.085 Uiso 1 1 calc R U . . .
H28B H 0.657267 0.990282 0.393364 0.085 Uiso 1 1 calc R U . . .
H28C H 0.529130 0.947391 0.332874 0.085 Uiso 1 1 calc R U . . .
N5 N 0.3297(4) 0.92803(16) 0.4649(2) 0.1042(11) Uani 1 1 d . . . . .
C25 C 0.3458(3) 0.87107(14) 0.47607(18) 0.0587(6) Uani 1 1 d . . . . .
C26 C 0.3716(3) 0.79959(12) 0.49312(17) 0.0613(7) Uani 1 1 d . . . . .
H26A H 0.471474 0.792328 0.521149 0.092 Uiso 1 1 calc R U . . .
H26B H 0.345279 0.774496 0.434676 0.092 Uiso 1 1 calc R U . . .
H26C H 0.315482 0.783091 0.535190 0.092 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
Cu1 O1 1.9532(8) . ?
Cu1 O1 1.9533(8) 3_666 ?
Cu1 N1 1.9985(10) 4_575 ?
Cu1 N1 1.9985(9) 2_646 ?
O1 C1 1.2801(14) . ?
O2 C1 1.2506(14) . ?
N1 C9 1.3399(14) . ?
N1 N2 1.3571(14) . ?
N2 C10 1.3396(14) . ?
N2 H2 0.87(2) . ?
C1 C2 1.4959(15) . ?
C2 C7 1.3917(16) . ?
C2 C3 1.3920(16) . ?
C3 C4 1.3894(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.3984(16) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3993(16) . ?
C5 C8 1.4724(15) . ?
C6 C7 1.3896(16) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C10 1.3937(16) . ?
C8 C9 1.4174(16) . ?
C9 C11 1.4925(17) . ?
C10 C12 1.4914(18) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
Cu2 O3 1.9369(8) 3_766 ?
Cu2 O3 1.9370(8) . ?
Cu2 N3 1.9610(10) 4_575 ?
Cu2 N3 1.9610(10) 2_746 ?
O3 C13 1.2758(14) . ?
O4 C13 1.2355(14) . ?
N3 C21 1.3307(14) . ?
N3 N4 1.3546(15) . ?
N4 C22 1.3454(15) . ?
N4 H4 0.83(2) . ?
C13 C14 1.5017(15) . ?
C14 C19 1.3923(16) . ?
C14 C15 1.3952(16) . ?
C15 C16 1.3873(16) . ?
C15 H15 0.9500 . ?
C16 C17 1.3992(16) . ?
C16 H16 0.9500 . ?
C17 C18 1.4000(16) . ?
C17 C20 1.4684(15) . ?
C18 C19 1.3890(15) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C22 1.3946(16) . ?
C20 C21 1.4171(16) . ?
C21 C23 1.4904(17) . ?
C22 C24 1.4927(18) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N6 C27 1.128(3) . ?
C27 C28 1.438(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
N5 C25 1.133(4) . ?
C25 C26 1.434(4) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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 . 3_666 ?
O1 Cu1 N1 90.44(4) . 4_575 ?
O1 Cu1 N1 89.57(4) 3_666 4_575 ?
O1 Cu1 N1 89.56(4) . 2_646 ?
O1 Cu1 N1 90.43(4) 3_666 2_646 ?
N1 Cu1 N1 180.00(4) 4_575 2_646 ?
C1 O1 Cu1 106.38(7) . . ?
C9 N1 N2 106.15(9) . . ?
C9 N1 Cu1 134.95(8) . 2_656 ?
N2 N1 Cu1 118.90(7) . 2_656 ?
C10 N2 N1 112.20(10) . . ?
C10 N2 H2 126.6(13) . . ?
N1 N2 H2 120.9(13) . . ?
O2 C1 O1 122.95(10) . . ?
O2 C1 C2 120.40(10) . . ?
O1 C1 C2 116.61(10) . . ?
C7 C2 C3 119.48(10) . . ?
C7 C2 C1 119.71(10) . . ?
C3 C2 C1 120.76(10) . . ?
C4 C3 C2 120.22(11) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.81(11) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C4 C5 C6 118.46(10) . . ?
C4 C5 C8 121.05(10) . . ?
C6 C5 C8 120.48(10) . . ?
C7 C6 C5 120.73(11) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C2 120.27(11) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C10 C8 C9 105.42(9) . . ?
C10 C8 C5 125.97(11) . . ?
C9 C8 C5 128.61(10) . . ?
N1 C9 C8 109.56(10) . . ?
N1 C9 C11 121.27(10) . . ?
C8 C9 C11 129.16(10) . . ?
N2 C10 C8 106.66(10) . . ?
N2 C10 C12 120.96(10) . . ?
C8 C10 C12 132.28(10) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 Cu2 O3 180.0 3_766 . ?
O3 Cu2 N3 94.55(4) 3_766 4_575 ?
O3 Cu2 N3 85.45(4) . 4_575 ?
O3 Cu2 N3 85.45(4) 3_766 2_746 ?
O3 Cu2 N3 94.55(4) . 2_746 ?
N3 Cu2 N3 180.0 4_575 2_746 ?
C13 O3 Cu2 131.45(8) . . ?
C21 N3 N4 106.76(10) . . ?
C21 N3 Cu2 130.81(9) . 2_756 ?
N4 N3 Cu2 122.40(7) . 2_756 ?
C22 N4 N3 111.90(10) . . ?
C22 N4 H4 128.5(15) . . ?
N3 N4 H4 118.4(15) . . ?
O4 C13 O3 126.76(10) . . ?
O4 C13 C14 118.69(10) . . ?
O3 C13 C14 114.55(10) . . ?
C19 C14 C15 119.27(10) . . ?
C19 C14 C13 121.30(10) . . ?
C15 C14 C13 119.37(10) . . ?
C16 C15 C14 120.22(11) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.92(11) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C18 118.47(10) . . ?
C16 C17 C20 119.29(10) . . ?
C18 C17 C20 122.24(10) . . ?
C19 C18 C17 120.59(10) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C14 120.51(10) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C22 C20 C21 105.64(10) . . ?
C22 C20 C17 129.05(11) . . ?
C21 C20 C17 125.26(10) . . ?
N3 C21 C20 109.41(10) . . ?
N3 C21 C23 121.33(11) . . ?
C20 C21 C23 129.14(10) . . ?
N4 C22 C20 106.28(11) . . ?
N4 C22 C24 120.94(11) . . ?
C20 C22 C24 132.76(11) . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N6 C27 C28 179.6(3) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N5 C25 C26 177.6(4) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
N2 H2 O4 0.87(2) 1.85(2) 2.6791(14) 158.2(19) 2_656
C11 H11C O1 0.98 2.32 3.0822(15) 134.3 4_576
C12 H12B O4 0.98 2.59 3.3808(16) 138.1 2_656
N4 H4 O2 0.83(2) 1.99(2) 2.7459(13) 150(2) 2_656
C23 H23B O2 0.98 2.51 3.4551(16) 161.9 4_676
C28 H28B N5 0.98 2.63 3.544(4) 155.7 3_676

_refine_diff_density_max         0.665
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.077


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile/water'
