#------------------------------------------------------------------------------
#$Date: 2025-07-06 19:56:00 +0300 (Sun, 06 Jul 2025) $
#$Revision: 300952 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/87/7718745.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7718745
loop_
_publ_author_name
'Khan, Yaqoot'
'Du, Yunyun'
'Yan, Li'
'Zhang, Niu'
'Zhang, Menglei'
'Ma, Hongwei'
'Li, Hui'
_publ_section_title
;
 Structural diversity of nucleotide coordination polymers of cytidine
 mono-, di-, and tri-phosphates and their selective recognition of
 tryptophan and tyrosine.
;
_journal_issue                   23
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9145
_journal_page_last               9159
_journal_paper_doi               10.1039/d5dt00786k
_journal_volume                  54
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H24 Cu N5 O9 P, 3.5(H2 O)'
_chemical_formula_sum            'C19 H31 Cu N5 O12.5 P'
_chemical_formula_weight         624.00
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2kdfjy
_audit_creation_date             2023-10-20
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-06-25 deposited with the CCDC.	2025-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.0705(4)
_cell_length_b                   22.3081(10)
_cell_length_c                   20.3416(9)
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    284.07
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.28
_cell_volume                     5023.6(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      284.07
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            43457
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.365
_diffrn_reflns_theta_min         2.285
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.008
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6888
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0742 before and 0.0591 after correction.
The Ratio of minimum to maximum transmission is 0.9237.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear greenish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_description       block
_exptl_crystal_F_000             2592
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.012(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         6253
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0323
_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)+(0.0377P)²+3.9764P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0780
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                5200
_reflns_number_total             6253
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5dt00786k2.cif
_cod_data_source_block           a_b
_cod_depositor_comments
'Adding full bibliography for 7718743--7718747.cif.'
_cod_original_formula_sum        'C19 H31 Cu N5 O12.50 P'
_cod_database_code               7718745
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.787
_shelx_estimated_absorpt_t_min   0.739
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.988(15)
 0.012(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
3. Restrained distances
 H11A-H12B
 2.2 with sigma of 0.02
 H12B-H15
 2.1 with sigma of 0.02
 H15-H12B
 2.2 with sigma of 0.02
4. Others
 Fixed Sof: H13C(0.5) H13D(0.5)
5.a Free rotating group:
 O13(H13C,H13D), O10(H10A,H10B), O11(H11A,H11B), O12(H12A,H12B)
5.b Rotating group:
 O1(H1A,H1B), O3(H3A,H3B)
5.c Ternary CH refined with riding coordinates:
 C14(H14), C15(H15), C17(H17)
5.d Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B)
5.e Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C20(H20),
 C21(H21)
5.f X=CH2 refined with riding coordinates:
 N7(H7A,H7B)
5.g Idealised tetrahedral OH refined as rotating group:
 O8(H8A)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, -z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'
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
P1 P -0.25663(8) 0.11742(3) -0.17115(4) 0.01487(15) Uani 1 1 d . . . . .
O1 O -0.4467(2) 0.10156(12) -0.36779(13) 0.0298(6) Uani 1 1 d . . . . .
H1A H -0.509394 0.093520 -0.390234 0.045 Uiso 1 1 d R U . . .
H1B H -0.399542 0.072083 -0.374624 0.045 Uiso 1 1 d R U . . .
N1 N -0.500000 0.19624(16) -0.250000 0.0171(8) Uani 1 2 d S T P . .
C1 C -0.5584(3) 0.22709(15) -0.20385(18) 0.0212(7) Uani 1 1 d . . . . .
H1 H -0.599165 0.206011 -0.171243 0.025 Uiso 1 1 calc R U . . .
Cu1 Cu -0.500000 0.10545(2) -0.250000 0.01510(13) Uani 1 2 d S T P . .
Cu2 Cu 0.000000 0.10635(2) -0.250000 0.01501(12) Uani 1 2 d S T P . .
O2 O -0.32343(18) 0.10430(10) -0.23519(11) 0.0183(5) Uani 1 1 d . . . . .
C2 C -0.5612(3) 0.28911(16) -0.20220(18) 0.0229(8) Uani 1 1 d . . . . .
H2 H -0.603679 0.308947 -0.169312 0.027 Uiso 1 1 calc R U . . .
N2 N -0.500000 0.51370(16) -0.250000 0.0175(8) Uani 1 2 d S T P . .
N3 N 0.000000 0.19704(16) -0.250000 0.0191(8) Uani 1 2 d S T P . .
O3 O 0.1534(2) 0.10815(12) -0.16316(14) 0.0302(6) Uani 1 1 d . . . . .
H3A H 0.223431 0.105601 -0.180241 0.045 Uiso 1 1 d R U . . .
H3B H 0.147111 0.076610 -0.139811 0.045 Uiso 1 1 d R U . . .
C3 C -0.500000 0.3214(2) -0.250000 0.0194(9) Uani 1 2 d S T P . .
N4 N 0.000000 0.51335(16) -0.250000 0.0181(8) Uani 1 2 d S T P . .
O4 O -0.12190(18) 0.10622(11) -0.17884(11) 0.0196(5) Uani 1 1 d . . . . .
C4 C -0.500000 0.3880(2) -0.250000 0.0201(9) Uani 1 2 d S T P . .
C5 C -0.3936(3) 0.42035(14) -0.2542(2) 0.0260(7) Uani 1 1 d . . . . .
H5 H -0.319935 0.400463 -0.257206 0.031 Uiso 1 1 calc R U . . .
N5 N -0.2860(3) 0.40625(12) -0.08125(15) 0.0248(7) Uani 1 1 d . . . . .
O5 O -0.3070(2) 0.08484(11) -0.11255(12) 0.0237(5) Uani 1 1 d . . . . .
O6 O -0.2782(2) 0.18810(10) -0.16101(12) 0.0237(5) Uani 1 1 d . . . . .
N6 N -0.3829(3) 0.49994(14) -0.09419(15) 0.0253(7) Uani 1 1 d . . . . .
C6 C -0.3971(3) 0.48265(14) -0.2539(2) 0.0242(7) Uani 1 1 d . . . . .
H6 H -0.324602 0.503613 -0.256585 0.029 Uiso 1 1 calc R U . . .
O7 O -0.2227(2) 0.31621(11) -0.12740(13) 0.0307(6) Uani 1 1 d . . . . .
N7 N -0.5880(3) 0.50664(16) -0.08198(16) 0.0339(8) Uani 1 1 d . . . . .
H7A H -0.584990 0.543270 -0.095059 0.041 Uiso 1 1 calc R U . . .
H7B H -0.656275 0.490841 -0.071581 0.041 Uiso 1 1 calc R U . . .
C7 C 0.0639(3) 0.48275(15) -0.20552(17) 0.0196(7) Uani 1 1 d . . . . .
H7 H 0.108073 0.503904 -0.174315 0.023 Uiso 1 1 calc R U . . .
C8 C 0.0668(3) 0.42074(15) -0.20415(17) 0.0202(7) Uani 1 1 d . . . . .
H8 H 0.113029 0.400910 -0.172794 0.024 Uiso 1 1 calc R U . . .
O8 O -0.0736(3) 0.24526(15) 0.00828(17) 0.0493(9) Uani 1 1 d . . . . .
H8A H -0.003693 0.254201 -0.000776 0.074 Uiso 1 1 calc R U . . .
O9 O -0.1801(3) 0.49001(12) -0.10667(16) 0.0375(7) Uani 1 1 d . . . . .
C9 C 0.000000 0.3881(2) -0.250000 0.0180(9) Uani 1 2 d S T P . .
C10 C 0.000000 0.32186(19) -0.250000 0.0172(9) Uani 1 2 d S T P . .
C11 C 0.1017(3) 0.28964(15) -0.23246(17) 0.0206(7) Uani 1 1 d . . . . .
H11 H 0.171862 0.309588 -0.220005 0.025 Uiso 1 1 calc R U . . .
C12 C 0.0989(3) 0.22797(15) -0.23347(17) 0.0210(7) Uani 1 1 d . . . . .
H12 H 0.168481 0.206988 -0.222229 0.025 Uiso 1 1 calc R U . . .
C13 C -0.2699(4) 0.21405(16) -0.09726(18) 0.0322(9) Uani 1 1 d . . . . .
H13A H -0.247911 0.183258 -0.065782 0.039 Uiso 1 1 calc R U . . .
H13B H -0.348176 0.229857 -0.084723 0.039 Uiso 1 1 calc R U . . .
C14 C -0.1779(3) 0.26359(15) -0.09492(18) 0.0238(7) Uani 1 1 d . . . . .
H14 H -0.102514 0.250394 -0.115656 0.029 Uiso 1 1 calc R U . . .
C15 C -0.1537(4) 0.28387(17) -0.0257(2) 0.0329(9) Uani 1 1 d . . . . .
H15 H -0.230626 0.284587 -0.001854 0.039 Uiso 1 1 calc DR U . . .
C16 C -0.1111(4) 0.34732(18) -0.0340(2) 0.0399(10) Uani 1 1 d . . . . .
H16A H -0.024522 0.348872 -0.041137 0.048 Uiso 1 1 calc R U . . .
H16B H -0.131191 0.371437 0.004173 0.048 Uiso 1 1 calc R U . . .
C17 C -0.1794(3) 0.36833(16) -0.0942(2) 0.0293(9) Uani 1 1 d . . . . .
H17 H -0.123842 0.389985 -0.123219 0.035 Uiso 1 1 calc R U . . .
C18 C -0.2802(3) 0.46735(16) -0.09442(18) 0.0258(8) Uani 1 1 d . . . . .
C19 C -0.4876(3) 0.47457(16) -0.07784(17) 0.0257(7) Uani 1 1 d . . . . .
C20 C -0.4923(4) 0.41376(16) -0.0565(2) 0.0336(9) Uani 1 1 d . . . . .
H20 H -0.563134 0.397272 -0.039881 0.040 Uiso 1 1 calc R U . . .
C21 C -0.3920(3) 0.38152(18) -0.0612(2) 0.0330(9) Uani 1 1 d . . . . .
H21 H -0.394269 0.341010 -0.050461 0.040 Uiso 1 1 calc R U . . .
O13 O -0.0170(4) 0.500000 0.000000 0.0478(11) Uani 1 2 d GS T P . .
H13C H -0.074239 0.495090 0.027341 0.072 Uiso 0.5 1 d G U P . .
H13D H -0.049363 0.493587 -0.037269 0.072 Uiso 0.5 1 d G U P . .
O10 O -0.3056(3) 0.07413(15) 0.02021(14) 0.0431(7) Uani 1 1 d G . . . .
H10A H -0.377145 0.060337 0.021863 0.065 Uiso 1 1 d G U . . .
H10B H -0.293926 0.081578 -0.020247 0.065 Uiso 1 1 d G U . . .
O11 O -0.2484(4) 0.18118(15) 0.08194(16) 0.0539(8) Uani 1 1 d G . . . .
H11A H -0.299705 0.208990 0.075700 0.081 Uiso 1 1 d DG U . . .
H11B H -0.278998 0.147770 0.070969 0.081 Uiso 1 1 d G U . . .
O12 O -0.3815(4) 0.28950(17) 0.0786(2) 0.0609(10) Uani 1 1 d G . . . .
H12A H -0.431372 0.318344 0.076179 0.091 Uiso 1 1 d G U . . .
H12B H -0.315362 0.305794 0.090188 0.091 Uiso 1 1 d DG U . . .
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O2 P1 O6 103.04(12) . . ?
O4 P1 O2 110.86(13) . . ?
O4 P1 O6 108.65(13) . . ?
O5 P1 O2 113.85(13) . . ?
O5 P1 O4 111.47(14) . . ?
O5 P1 O6 108.50(13) . . ?
H1A O1 H1B 104.5 . . ?
Cu1 O1 H1A 109.5 . . ?
Cu1 O1 H1B 109.4 . . ?
C1 N1 C1 117.7(4) 4_454 . ?
C1 N1 Cu1 121.1(2) 4_454 . ?
C1 N1 Cu1 121.1(2) . . ?
N1 C1 H1 118.5 . . ?
N1 C1 C2 123.0(3) . . ?
C2 C1 H1 118.5 . . ?
N1 Cu1 O1 92.01(6) . . ?
N1 Cu1 N4 180.0 . 5_445 ?
O2 Cu1 O1 84.90(9) . . ?
O2 Cu1 O1 95.05(9) 4_454 . ?
O2 Cu1 N1 90.74(6) 4_454 . ?
O2 Cu1 N1 90.74(6) . . ?
O2 Cu1 O2 178.51(13) 4_454 . ?
O2 Cu1 N4 89.26(6) 4_454 5_445 ?
O2 Cu1 N4 89.26(6) . 5_445 ?
N4 Cu1 O1 87.99(6) 5_445 . ?
N2 Cu2 O3 90.94(6) 5_545 . ?
N3 Cu2 N2 180.0 . 5_545 ?
N3 Cu2 O3 89.06(6) . . ?
O4 Cu2 N2 89.91(7) 4_554 5_545 ?
O4 Cu2 N2 89.91(7) . 5_545 ?
O4 Cu2 N3 90.09(7) . . ?
O4 Cu2 N3 90.09(7) 4_554 . ?
O4 Cu2 O3 93.13(9) 4_554 . ?
O4 Cu2 O3 86.87(9) . . ?
O4 Cu2 O4 179.83(14) . 4_554 ?
P1 O2 Cu1 127.33(13) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
C6 N2 Cu2 121.23(19) 4_454 5_455 ?
C6 N2 Cu2 121.23(19) . 5_455 ?
C6 N2 C6 117.5(4) 4_454 . ?
C12 N3 Cu2 121.07(19) . . ?
C12 N3 Cu2 121.06(19) 4_554 . ?
C12 N3 C12 117.9(4) 4_554 . ?
Cu2 O3 H3A 109.6 . . ?
Cu2 O3 H3B 109.4 . . ?
H3A O3 H3B 104.3 . . ?
C2 C3 C2 117.4(4) 4_454 . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 C4 121.3(2) 4_454 . ?
C7 N4 Cu1 120.7(2) 4_554 5 ?
C7 N4 Cu1 120.7(2) . 5 ?
C7 N4 C7 118.5(4) 4_554 . ?
P1 O4 Cu2 138.07(14) . . ?
C5 C4 C3 121.4(2) . . ?
C5 C4 C3 121.4(2) 4_454 . ?
C5 C4 C5 117.2(4) 4_454 . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C18 N5 C17 119.3(3) . . ?
C21 N5 C17 120.8(3) . . ?
C21 N5 C18 119.7(3) . . ?
C13 O6 P1 120.4(2) . . ?
C19 N6 C18 120.3(3) . . ?
N2 C6 C5 122.8(3) . . ?
N2 C6 H6 118.6 . . ?
C5 C6 H6 118.6 . . ?
C17 O7 C14 109.4(3) . . ?
H7A N7 H7B 120.0 . . ?
C19 N7 H7A 120.0 . . ?
C19 N7 H7B 120.0 . . ?
N4 C7 H7 118.8 . . ?
N4 C7 C8 122.4(3) . . ?
C8 C7 H7 118.8 . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C15 O8 H8A 109.5 . . ?
C8 C9 C8 117.1(4) . 4_554 ?
C8 C9 C10 121.5(2) . . ?
C8 C9 C10 121.5(2) 4_554 . ?
C11 C10 C9 121.3(2) . . ?
C11 C10 C9 121.3(2) 4_554 . ?
C11 C10 C11 117.4(4) 4_554 . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
N3 C12 C11 122.6(3) . . ?
N3 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
O6 C13 H13A 109.3 . . ?
O6 C13 H13B 109.3 . . ?
O6 C13 C14 111.8(3) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
O7 C14 C13 110.6(3) . . ?
O7 C14 H14 110.0 . . ?
O7 C14 C15 104.3(3) . . ?
C13 C14 H14 110.0 . . ?
C13 C14 C15 111.8(3) . . ?
C15 C14 H14 110.0 . . ?
O8 C15 C14 112.7(3) . . ?
O8 C15 H15 108.3 . . ?
O8 C15 C16 115.6(4) . . ?
C14 C15 H15 108.3 . . ?
C16 C15 C14 103.5(3) . . ?
C16 C15 H15 108.3 . . ?
C15 C16 H16A 111.2 . . ?
C15 C16 H16B 111.2 . . ?
C15 C16 C17 103.1(3) . . ?
H16A C16 H16B 109.1 . . ?
C17 C16 H16A 111.2 . . ?
C17 C16 H16B 111.2 . . ?
N5 C17 C16 115.6(3) . . ?
N5 C17 H17 109.1 . . ?
O7 C17 N5 106.4(3) . . ?
O7 C17 C16 107.4(3) . . ?
O7 C17 H17 109.1 . . ?
C16 C17 H17 109.1 . . ?
N6 C18 N5 119.2(3) . . ?
O9 C18 N5 118.6(3) . . ?
O9 C18 N6 122.2(3) . . ?
N6 C19 C20 120.8(3) . . ?
N7 C19 N6 119.0(3) . . ?
N7 C19 C20 120.2(4) . . ?
C19 C20 H20 121.2 . . ?
C21 C20 C19 117.7(4) . . ?
C21 C20 H20 121.2 . . ?
N5 C21 H21 119.2 . . ?
C20 C21 N5 121.6(4) . . ?
C20 C21 H21 119.2 . . ?
H13C O13 H13C 83.7 . 3_565 ?
H13C O13 H13D 28.9 . 3_565 ?
H13C O13 H13D 104.4 . . ?
H13C O13 H13D 104.4 3_565 3_565 ?
H13D O13 H13C 28.9 . 3_565 ?
H13D O13 H13D 130.2 . 3_565 ?
H10A O10 H10B 104.5 . . ?
H11A O11 H11B 109.6 . . ?
H12A O12 H12B 104.6 . . ?
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
P1 O2 1.526(2) . ?
P1 O4 1.520(2) . ?
P1 O5 1.503(2) . ?
P1 O6 1.608(2) . ?
O1 H1A 0.8502 . ?
O1 H1B 0.8508 . ?
O1 Cu1 2.469(3) . ?
N1 C1 1.331(4) 4_454 ?
N1 C1 1.331(4) . ?
N1 Cu1 2.025(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.384(5) . ?
Cu1 O2 1.978(2) . ?
Cu1 O2 1.978(2) 4_454 ?
Cu1 N4 2.055(4) 5_445 ?
Cu2 N2 2.067(4) 5_545 ?
Cu2 N3 2.023(4) . ?
Cu2 O3 2.451(3) . ?
Cu2 O4 1.979(2) 4_554 ?
Cu2 O4 1.979(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(4) . ?
N2 C6 1.336(4) 4_454 ?
N2 C6 1.336(4) . ?
N3 C12 1.337(4) . ?
N3 C12 1.337(4) 4_554 ?
O3 H3A 0.8511 . ?
O3 H3B 0.8518 . ?
C3 C4 1.486(6) . ?
N4 C7 1.336(4) 4_554 ?
N4 C7 1.336(4) . ?
C4 C5 1.384(4) . ?
C4 C5 1.384(4) 4_454 ?
C5 H5 0.9300 . ?
C5 C6 1.390(4) . ?
N5 C17 1.476(5) . ?
N5 C18 1.391(4) . ?
N5 C21 1.359(5) . ?
O6 C13 1.423(4) . ?
N6 C18 1.350(5) . ?
N6 C19 1.333(5) . ?
C6 H6 0.9300 . ?
O7 C14 1.436(4) . ?
O7 C17 1.428(4) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N7 C19 1.325(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.384(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.395(4) . ?
O8 H8A 0.8200 . ?
O8 C15 1.416(5) . ?
O9 C18 1.243(4) . ?
C9 C10 1.477(6) . ?
C10 C11 1.383(4) . ?
C10 C11 1.383(4) 4_554 ?
C11 H11 0.9300 . ?
C11 C12 1.376(5) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.504(5) . ?
C14 H14 0.9800 . ?
C14 C15 1.504(5) . ?
C15 H15 0.9800 . ?
C15 C16 1.501(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.514(6) . ?
C17 H17 0.9800 . ?
C19 C20 1.425(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.326(5) . ?
C21 H21 0.9300 . ?
O13 H13C 0.8499 . ?
O13 H13C 0.85(13) 3_565 ?
O13 H13D 0.85(8) 3_565 ?
O13 H13D 0.8505 . ?
O10 H10A 0.8505 . ?
O10 H10B 0.8495 . ?
O11 H11A 0.8503 . ?
O11 H11B 0.8484 . ?
O12 H12A 0.8493 . ?
O12 H12B 0.8504 . ?
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
O1 H1A O5 0.85 2.04 2.781(4) 144.9 4_454 yes
O3 H3A O2 0.85 2.05 2.797(3) 146.8 4_554 yes
O3 H3B N6 0.85 1.97 2.821(4) 172.6 5_545 yes
O8 H8A O12 0.82 2.30 2.872(5) 127.3 7 yes
O13 H13C O9 0.85 2.02 2.832(4) 158.9 3_565 yes
O13 H13D O9 0.85 2.02 2.832(4) 158.4 . yes
O10 H10A O13 0.85 2.10 2.895(5) 155.6 5_445 yes
O10 H10B O5 0.85 1.88 2.711(4) 164.0 . yes
O11 H11A O12 0.85 2.01 2.831(5) 161.3 . yes
O11 H11B O10 0.85 1.96 2.771(5) 159.0 . 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
P1 O6 C13 C14 123.0(3) . . . . ?
N1 C1 C2 C3 -0.6(5) . . . . ?
C1 N1 C1 C2 0.3(3) 4_454 . . . ?
C1 C2 C3 C2 0.3(3) . . . 4_454 ?
C1 C2 C3 C4 -179.7(3) . . . . ?
Cu1 N1 C1 C2 -179.7(3) . . . . ?
Cu1 N4 C7 C8 -179.6(2) 5 . . . ?
Cu2 N2 C6 C5 -179.9(3) 5_455 . . . ?
Cu2 N3 C12 C11 -179.5(3) . . . . ?
O2 P1 O4 Cu2 26.6(3) . . . . ?
O2 P1 O6 C13 156.9(3) . . . . ?
C2 C3 C4 C5 129.0(3) . . . . ?
C2 C3 C4 C5 -51.0(3) 4_454 . . . ?
C2 C3 C4 C5 129.0(3) 4_454 . . 4_454 ?
C2 C3 C4 C5 -51.0(3) . . . 4_454 ?
C3 C4 C5 C6 -179.9(3) . . . . ?
N4 C7 C8 C9 -0.8(5) . . . . ?
O4 P1 O2 Cu1 174.85(15) . . . . ?
O4 P1 O6 C13 -85.5(3) . . . . ?
C4 C5 C6 N2 -0.3(6) . . . . ?
C5 C4 C5 C6 0.1(3) 4_454 . . . ?
O5 P1 O2 Cu1 48.2(2) . . . . ?
O5 P1 O4 Cu2 154.5(2) . . . . ?
O5 P1 O6 C13 35.9(3) . . . . ?
O6 P1 O2 Cu1 -69.08(18) . . . . ?
O6 P1 O4 Cu2 -86.0(2) . . . . ?
O6 C13 C14 O7 74.0(4) . . . . ?
O6 C13 C14 C15 -170.3(3) . . . . ?
N6 C19 C20 C21 -8.1(6) . . . . ?
C6 N2 C6 C5 0.1(3) 4_454 . . . ?
O7 C14 C15 O8 -160.6(3) . . . . ?
O7 C14 C15 C16 -35.0(4) . . . . ?
N7 C19 C20 C21 171.6(4) . . . . ?
C7 N4 C7 C8 0.4(2) 4_554 . . . ?
C7 C8 C9 C8 0.4(2) . . . 4_554 ?
C7 C8 C9 C10 -179.6(2) . . . . ?
C8 C9 C10 C11 -34.0(2) 4_554 . . 4_554 ?
C8 C9 C10 C11 -34.0(2) . . . . ?
C8 C9 C10 C11 146.0(2) . . . 4_554 ?
C8 C9 C10 C11 146.0(2) 4_554 . . . ?
O8 C15 C16 C17 155.3(3) . . . . ?
C9 C10 C11 C12 -179.5(2) . . . . ?
C10 C11 C12 N3 -1.0(5) . . . . ?
C11 C10 C11 C12 0.5(2) 4_554 . . . ?
C12 N3 C12 C11 0.5(3) 4_554 . . . ?
C13 C14 C15 O8 79.9(4) . . . . ?
C13 C14 C15 C16 -154.6(3) . . . . ?
C14 O7 C17 N5 -129.0(3) . . . . ?
C14 O7 C17 C16 -4.6(4) . . . . ?
C14 C15 C16 C17 31.6(4) . . . . ?
C15 C16 C17 N5 101.2(4) . . . . ?
C15 C16 C17 O7 -17.3(4) . . . . ?
C17 N5 C18 N6 168.0(3) . . . . ?
C17 N5 C18 O9 -11.4(5) . . . . ?
C17 N5 C21 C20 -172.2(4) . . . . ?
C17 O7 C14 C13 145.1(3) . . . . ?
C17 O7 C14 C15 24.8(4) . . . . ?
C18 N5 C17 O7 -134.3(3) . . . . ?
C18 N5 C17 C16 106.6(4) . . . . ?
C18 N5 C21 C20 3.0(6) . . . . ?
C18 N6 C19 N7 -175.9(3) . . . . ?
C18 N6 C19 C20 3.8(5) . . . . ?
C19 N6 C18 N5 3.8(5) . . . . ?
C19 N6 C18 O9 -176.9(4) . . . . ?
C19 C20 C21 N5 4.5(6) . . . . ?
C21 N5 C17 O7 40.9(5) . . . . ?
C21 N5 C17 C16 -78.2(5) . . . . ?
C21 N5 C18 N6 -7.4(5) . . . . ?
C21 N5 C18 O9 173.3(4) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.988(15)
2 0.012(15)
