#------------------------------------------------------------------------------
#$Date: 2025-11-29 21:28:46 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303754 $
#$URL: svn://www.crystallography.net/cod/cif/7/71/96/7719606.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_7719606
loop_
_publ_author_name
'Archer, Emma M.'
'Vigil, Correy R.'
'Galley, Shane S.'
'Jackson, Jessica A.'
'Shafer, Jenifer C.'
_publ_section_title
;
 Unveiling the interplay: comparing solvent extraction, structure, and
 stability constants in a phenanthroline diamide system with trivalent
 lanthanides.
;
_journal_issue                   43
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              16086
_journal_page_last               16094
_journal_paper_doi               10.1039/d5dt01636c
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C22 H26 Ho N7 O11'
_chemical_formula_sum            'C22 H26 Ho N7 O11'
_chemical_formula_weight         729.43
_chemical_name_systematic        Ho_TEtDAPhen
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-02-07
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-05-12 deposited with the CCDC.	2025-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.835(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.584(4)
_cell_length_b                   17.569(7)
_cell_length_c                   16.203(7)
_cell_measurement_reflns_used    8916
_cell_measurement_temperature    100
_cell_measurement_theta_max      20.454
_cell_measurement_theta_min      2.490
_cell_volume                     2709(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            87354
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         20.594
_diffrn_reflns_theta_min         2.490
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.601
_exptl_absorpt_correction_T_max  0.7171
_exptl_absorpt_correction_T_min  0.6175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1545 before and 0.1025 after correction.
The Ratio of minimum to maximum transmission is 0.8611.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.788
_exptl_crystal_description       prism
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.157
_refine_diff_density_max         1.000
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         5526
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0329P)²+1.9433P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0775
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4887
_reflns_number_total             5526
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5dt01636c8.cif
_cod_data_source_block           ag_ho_tetdaphen
_cod_depositor_comments
'Adding full bibliography for 7719600--7719609.cif.'
_cod_original_cell_volume        2709.0(19)
_cod_database_code               7719606
_shelx_shelxl_version_number     2019/3
_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   0.705
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C14-C15 \\sim C14-C16A
 with sigma of 0.02
3. Others
 Sof(H14C)=Sof(H14D)=Sof(C16A)=Sof(H16C)=Sof(H16D)=Sof(H16E)=1-FVAR(1)
 Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C14(H14C,H14D), C16(H16A,H16B), C21(H21A,H21B), C19(H19A,H19B)
4.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C3(H3), C2(H2), C6(H6), C5(H5)
4.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C15(H15A,H15B,
 H15C), C16A(H16C,H16D,H16E)
;
_olex2_submission_special_instructions 'No special instructions were received'
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'
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
Ho1 Ho 0.76416(2) 0.43938(2) 0.27741(2) 0.04056(7) Uani 1 1 d . . . . .
O9 O 0.9595(3) 0.53046(16) 0.29919(17) 0.0601(6) Uani 1 1 d . . . . .
O10 O 0.8426(2) 0.51122(14) 0.40218(14) 0.0533(6) Uani 1 1 d . . . . .
O1 O 0.6313(3) 0.55555(13) 0.25461(17) 0.0506(6) Uani 1 1 d . . . . .
O2 O 0.9604(3) 0.36532(14) 0.32802(16) 0.0558(6) Uani 1 1 d . . . . .
O11 O 1.0168(4) 0.5917(2) 0.4145(2) 0.0874(10) Uani 1 1 d . . . . .
N7 N 0.9430(3) 0.54618(17) 0.3736(2) 0.0533(7) Uani 1 1 d . . . . .
O6 O 0.8589(3) 0.37964(16) 0.15899(17) 0.0641(7) Uani 1 1 d . . . . .
N1 N 0.4136(3) 0.5900(2) 0.1985(2) 0.0589(7) Uani 1 1 d . . . . .
N3 N 0.7466(3) 0.35376(14) 0.40619(16) 0.0433(6) Uani 1 1 d . . . . .
C10 C 0.7303(4) 0.2667(2) 0.5472(2) 0.0603(9) Uani 1 1 d . . . . .
H10 H 0.726011 0.237574 0.594753 0.072 Uiso 1 1 calc R U . . .
O3 O 0.6275(3) 0.31870(16) 0.24636(19) 0.0692(7) Uani 1 1 d . . . . .
N4 N 1.0693(3) 0.26010(19) 0.3786(2) 0.0646(8) Uani 1 1 d . . . . .
C8 C 0.6329(3) 0.35749(17) 0.44801(19) 0.0442(7) Uani 1 1 d . . . . .
O7 O 0.8118(3) 0.49747(17) 0.14263(17) 0.0698(7) Uani 1 1 d . . . . .
N5 N 0.5346(3) 0.3508(2) 0.1960(2) 0.0691(10) Uani 1 1 d . . . . .
C11 C 0.8457(4) 0.2620(2) 0.5056(2) 0.0559(8) Uani 1 1 d . . . . .
H11 H 0.920390 0.230275 0.524697 0.067 Uiso 1 1 calc R U . . .
C3 C 0.3030(4) 0.4720(2) 0.4273(2) 0.0557(8) Uani 1 1 d . . . . .
H3 H 0.221176 0.478364 0.452190 0.067 Uiso 1 1 calc R U . . .
C9 C 0.6192(4) 0.31440(19) 0.5195(2) 0.0528(8) Uani 1 1 d . . . . .
O8 O 0.8792(4) 0.4326(2) 0.0404(2) 0.0898(11) Uani 1 1 d . . . . .
C12 C 0.8495(3) 0.30607(17) 0.4333(2) 0.0456(7) Uani 1 1 d . . . . .
O5 O 0.4261(4) 0.3165(2) 0.1707(3) 0.1202(16) Uani 1 1 d . . . . .
C2 C 0.3263(4) 0.5159(2) 0.3608(2) 0.0557(8) Uani 1 1 d . . . . .
H2 H 0.261460 0.552853 0.340733 0.067 Uiso 1 1 calc R U . . .
O4 O 0.5579(3) 0.41772(19) 0.17416(18) 0.0670(7) Uani 1 1 d . . . . .
N6 N 0.8508(4) 0.43671(19) 0.1112(2) 0.0595(8) Uani 1 1 d . . . . .
N2 N 0.5457(3) 0.45275(15) 0.34998(17) 0.0424(6) Uani 1 1 d . . . . .
C7 C 0.5233(3) 0.40986(18) 0.41705(19) 0.0439(7) Uani 1 1 d . . . . .
C4 C 0.4029(4) 0.4169(2) 0.4584(2) 0.0512(8) Uani 1 1 d . . . . .
C14 C 0.2597(4) 0.5795(3) 0.1824(3) 0.0764(13) Uani 1 1 d D . . . .
H14A H 0.218619 0.593709 0.232086 0.092 Uiso 0.706(10) 1 calc R U P A 1
H14B H 0.223140 0.614125 0.138453 0.092 Uiso 0.706(10) 1 calc R U P A 1
H14C H 0.233148 0.531733 0.206184 0.092 Uiso 0.294(10) 1 calc R U P A 2
H14D H 0.230550 0.578166 0.123013 0.092 Uiso 0.294(10) 1 calc R U P A 2
C6 C 0.4934(5) 0.3234(2) 0.5599(3) 0.0664(10) Uani 1 1 d . . . . .
H6 H 0.483694 0.295170 0.607421 0.080 Uiso 1 1 calc R U . . .
C5 C 0.3909(4) 0.3713(2) 0.5307(2) 0.0639(10) Uani 1 1 d . . . . .
H5 H 0.310713 0.375145 0.557624 0.077 Uiso 1 1 calc R U . . .
C16 C 0.4759(5) 0.6378(3) 0.1364(3) 0.0777(13) Uani 1 1 d . . . . .
H16A H 0.569853 0.653115 0.159175 0.093 Uiso 1 1 calc R U . . .
H16B H 0.419786 0.683463 0.125767 0.093 Uiso 1 1 calc R U . . .
C18 C 0.9670(3) 0.31069(19) 0.3780(2) 0.0490(7) Uani 1 1 d . . . . .
C13 C 0.5011(4) 0.55269(18) 0.2542(2) 0.0472(7) Uani 1 1 d . . . . .
C1 C 0.4496(3) 0.50472(19) 0.32268(19) 0.0449(7) Uani 1 1 d . . . . .
C21 C 1.1757(4) 0.2731(3) 0.3203(3) 0.0752(12) Uani 1 1 d . . . . .
H21A H 1.265163 0.251981 0.343990 0.090 Uiso 1 1 calc R U . . .
H21B H 1.188168 0.327387 0.313098 0.090 Uiso 1 1 calc R U . . .
C19 C 1.0776(5) 0.1840(3) 0.4207(3) 0.0804(13) Uani 1 1 d . . . . .
H19A H 0.984845 0.169923 0.433748 0.097 Uiso 1 1 calc R U . . .
H19B H 1.106794 0.146171 0.382641 0.097 Uiso 1 1 calc R U . . .
C22 C 1.1324(6) 0.2372(3) 0.2374(4) 0.0987(17) Uani 1 1 d . . . . .
H22A H 1.199164 0.250036 0.199910 0.148 Uiso 1 1 calc R U . . .
H22B H 1.041129 0.255540 0.215448 0.148 Uiso 1 1 calc R U . . .
H22C H 1.129112 0.182874 0.243609 0.148 Uiso 1 1 calc R U . . .
C17 C 0.4828(6) 0.5964(4) 0.0565(3) 0.1062(19) Uani 1 1 d . . . . .
H17A H 0.518997 0.629789 0.017262 0.159 Uiso 1 1 calc R U . . .
H17B H 0.390347 0.579693 0.034688 0.159 Uiso 1 1 calc R U . . .
H17C H 0.543561 0.553037 0.066177 0.159 Uiso 1 1 calc R U . . .
C20 C 1.1761(6) 0.1829(4) 0.4975(4) 0.118(2) Uani 1 1 d . . . . .
H20A H 1.270769 0.182979 0.483776 0.176 Uiso 1 1 calc R U . . .
H20B H 1.160551 0.137925 0.528782 0.176 Uiso 1 1 calc R U . . .
H20C H 1.161149 0.227143 0.530123 0.176 Uiso 1 1 calc R U . . .
C15 C 0.2139(7) 0.5026(5) 0.1588(5) 0.093(3) Uani 0.706(10) 1 d D . P A 1
H15A H 0.262590 0.485408 0.113794 0.140 Uiso 0.706(10) 1 calc R U P A 1
H15B H 0.114576 0.502680 0.141500 0.140 Uiso 0.706(10) 1 calc R U P A 1
H15C H 0.234423 0.469185 0.205504 0.140 Uiso 0.706(10) 1 calc R U P A 1
C16A C 0.1898(18) 0.6443(9) 0.2209(11) 0.090(6) Uani 0.294(10) 1 d D . P A 2
H16C H 0.222335 0.646646 0.279200 0.135 Uiso 0.294(10) 1 calc R U P A 2
H16D H 0.089829 0.636864 0.213371 0.135 Uiso 0.294(10) 1 calc R U P A 2
H16E H 0.212196 0.691089 0.194800 0.135 Uiso 0.294(10) 1 calc R U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0013 0.0009 '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'
Ho Ho -0.2487 3.1417 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0058 0.0036 '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
O9 Ho1 N7 26.00(9) . . ?
O9 Ho1 N3 112.56(9) . . ?
O9 Ho1 O3 161.67(10) . . ?
O9 Ho1 O7 69.17(10) . . ?
O9 Ho1 N5 160.83(11) . . ?
O9 Ho1 O4 137.29(11) . . ?
O9 Ho1 N2 122.09(9) . . ?
O10 Ho1 O9 52.11(8) . . ?
O10 Ho1 N7 26.11(9) . . ?
O10 Ho1 O6 140.11(9) . . ?
O10 Ho1 N3 71.02(9) . . ?
O10 Ho1 O3 135.14(9) . . ?
O10 Ho1 O7 116.40(9) . . ?
O10 Ho1 N5 143.72(9) . . ?
O10 Ho1 O4 142.27(9) . . ?
O10 Ho1 N2 75.89(9) . . ?
O1 Ho1 O9 81.38(9) . . ?
O1 Ho1 O10 78.05(9) . . ?
O1 Ho1 N7 78.49(9) . . ?
O1 Ho1 O6 118.69(10) . . ?
O1 Ho1 N3 122.04(8) . . ?
O1 Ho1 O3 115.51(11) . . ?
O1 Ho1 O7 70.65(9) . . ?
O1 Ho1 N5 91.51(11) . . ?
O1 Ho1 O4 70.13(10) . . ?
O1 Ho1 N2 62.71(8) . . ?
O2 Ho1 O9 75.29(10) . . ?
O2 Ho1 O10 80.88(9) . . ?
O2 Ho1 O1 155.14(9) . . ?
O2 Ho1 N7 76.78(9) . . ?
O2 Ho1 O6 71.41(9) . . ?
O2 Ho1 N3 61.63(8) . . ?
O2 Ho1 O3 88.81(10) . . ?
O2 Ho1 O7 107.97(9) . . ?
O2 Ho1 N5 113.33(12) . . ?
O2 Ho1 O4 134.04(10) . . ?
O2 Ho1 N2 124.10(9) . . ?
N7 Ho1 N5 167.00(9) . . ?
O6 Ho1 O9 92.54(10) . . ?
O6 Ho1 N7 116.82(10) . . ?
O6 Ho1 N3 116.52(9) . . ?
O6 Ho1 O3 73.44(10) . . ?
O6 Ho1 O7 50.87(10) . . ?
O6 Ho1 N5 75.22(10) . . ?
O6 Ho1 O4 75.20(10) . . ?
O6 Ho1 N2 143.74(9) . . ?
N3 Ho1 N7 91.94(9) . . ?
N3 Ho1 N5 86.32(11) . . ?
O3 Ho1 N7 157.42(10) . . ?
O3 Ho1 N3 65.75(9) . . ?
O3 Ho1 N5 26.01(11) . . ?
O3 Ho1 N2 74.39(9) . . ?
O7 Ho1 N7 92.76(10) . . ?
O7 Ho1 N3 167.17(9) . . ?
O7 Ho1 O3 108.34(10) . . ?
O7 Ho1 N5 91.69(11) . . ?
O7 Ho1 N2 127.93(10) . . ?
O4 Ho1 N7 148.05(10) . . ?
O4 Ho1 N3 109.46(10) . . ?
O4 Ho1 O3 51.40(11) . . ?
O4 Ho1 O7 71.64(11) . . ?
O4 Ho1 N5 25.65(11) . . ?
O4 Ho1 N2 71.85(10) . . ?
N2 Ho1 N7 99.23(9) . . ?
N2 Ho1 N3 62.84(8) . . ?
N2 Ho1 N5 68.54(9) . . ?
N7 O9 Ho1 95.72(19) . . ?
N7 O10 Ho1 96.96(19) . . ?
C13 O1 Ho1 118.4(2) . . ?
C18 O2 Ho1 128.7(2) . . ?
O9 N7 Ho1 58.28(17) . . ?
O9 N7 O10 115.2(3) . . ?
O10 N7 Ho1 56.93(16) . . ?
O11 N7 Ho1 179.1(3) . . ?
O11 N7 O9 122.3(3) . . ?
O11 N7 O10 122.5(4) . . ?
N6 O6 Ho1 98.0(2) . . ?
C14 N1 C16 115.0(3) . . ?
C13 N1 C14 126.4(3) . . ?
C13 N1 C16 117.7(3) . . ?
C8 N3 Ho1 120.6(2) . . ?
C12 N3 Ho1 121.0(2) . . ?
C12 N3 C8 118.4(3) . . ?
C11 C10 H10 119.5 . . ?
C11 C10 C9 120.9(3) . . ?
C9 C10 H10 119.5 . . ?
N5 O3 Ho1 93.6(2) . . ?
C18 N4 C21 117.1(3) . . ?
C18 N4 C19 127.1(3) . . ?
C21 N4 C19 115.0(3) . . ?
N3 C8 C9 123.3(3) . . ?
N3 C8 C7 117.0(3) . . ?
C9 C8 C7 119.7(3) . . ?
N6 O7 Ho1 95.8(2) . . ?
O3 N5 Ho1 60.40(18) . . ?
O5 N5 Ho1 170.6(3) . . ?
O5 N5 O3 119.9(5) . . ?
O5 N5 O4 122.5(4) . . ?
O4 N5 Ho1 58.11(18) . . ?
O4 N5 O3 117.6(3) . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.7(3) . . ?
C12 C11 H11 120.7 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C10 C9 C8 116.7(3) . . ?
C10 C9 C6 124.6(3) . . ?
C8 C9 C6 118.6(3) . . ?
N3 C12 C11 122.0(3) . . ?
N3 C12 C18 110.2(3) . . ?
C11 C12 C18 127.8(3) . . ?
C3 C2 H2 120.3 . . ?
C3 C2 C1 119.4(3) . . ?
C1 C2 H2 120.3 . . ?
N5 O4 Ho1 96.2(2) . . ?
O6 N6 Ho1 56.59(17) . . ?
O7 N6 Ho1 58.72(18) . . ?
O7 N6 O6 115.1(3) . . ?
O8 N6 Ho1 175.6(3) . . ?
O8 N6 O6 121.9(3) . . ?
O8 N6 O7 123.0(4) . . ?
C7 N2 Ho1 122.5(2) . . ?
C1 N2 Ho1 119.1(2) . . ?
C1 N2 C7 118.4(3) . . ?
N2 C7 C8 117.0(3) . . ?
N2 C7 C4 123.3(3) . . ?
C4 C7 C8 119.7(3) . . ?
C3 C4 C5 123.9(3) . . ?
C7 C4 C3 116.7(3) . . ?
C7 C4 C5 119.3(3) . . ?
N1 C14 H14A 108.5 . . ?
N1 C14 H14B 108.5 . . ?
N1 C14 H14C 110.0 . . ?
N1 C14 H14D 110.0 . . ?
N1 C14 C16A 108.6(8) . . ?
H14A C14 H14B 107.5 . . ?
H14C C14 H14D 108.3 . . ?
C15 C14 N1 115.1(5) . . ?
C15 C14 H14A 108.5 . . ?
C15 C14 H14B 108.5 . . ?
C16A C14 H14C 110.0 . . ?
C16A C14 H14D 110.0 . . ?
C9 C6 H6 119.1 . . ?
C5 C6 C9 121.7(3) . . ?
C5 C6 H6 119.1 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
N1 C16 H16A 109.2 . . ?
N1 C16 H16B 109.2 . . ?
N1 C16 C17 111.9(4) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
O2 C18 N4 120.0(3) . . ?
O2 C18 C12 115.9(3) . . ?
N4 C18 C12 124.0(3) . . ?
O1 C13 N1 122.2(3) . . ?
O1 C13 C1 115.4(3) . . ?
N1 C13 C1 122.3(3) . . ?
C2 C1 C13 127.1(3) . . ?
N2 C1 C2 122.1(3) . . ?
N2 C1 C13 110.4(3) . . ?
N4 C21 H21A 109.3 . . ?
N4 C21 H21B 109.3 . . ?
N4 C21 C22 111.5(4) . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 H21A 109.3 . . ?
C22 C21 H21B 109.3 . . ?
N4 C19 H19A 109.0 . . ?
N4 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 N4 113.0(5) . . ?
C20 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16A H16C 109.5 . . ?
C14 C16A H16D 109.5 . . ?
C14 C16A H16E 109.5 . . ?
H16C C16A H16D 109.5 . . ?
H16C C16A H16E 109.5 . . ?
H16D C16A H16E 109.5 . . ?
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
Ho1 O9 2.456(3) . ?
Ho1 O10 2.426(2) . ?
Ho1 O1 2.411(2) . ?
Ho1 O2 2.353(2) . ?
Ho1 N7 2.873(3) . ?
Ho1 O6 2.454(3) . ?
Ho1 N3 2.594(3) . ?
Ho1 O3 2.511(3) . ?
Ho1 O7 2.501(3) . ?
Ho1 N5 2.883(3) . ?
Ho1 O4 2.462(3) . ?
Ho1 N2 2.531(3) . ?
O9 N7 1.266(4) . ?
O10 N7 1.274(4) . ?
O1 C13 1.248(4) . ?
O2 C18 1.252(4) . ?
O11 N7 1.211(4) . ?
O6 N6 1.264(4) . ?
N1 C14 1.478(5) . ?
N1 C16 1.488(5) . ?
N1 C13 1.329(5) . ?
N3 C8 1.351(4) . ?
N3 C12 1.329(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.365(5) . ?
C10 C9 1.387(5) . ?
O3 N5 1.266(5) . ?
N4 C18 1.322(4) . ?
N4 C21 1.488(5) . ?
N4 C19 1.499(5) . ?
C8 C9 1.403(5) . ?
C8 C7 1.441(5) . ?
O7 N6 1.259(4) . ?
N5 O5 1.230(4) . ?
N5 O4 1.255(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.410(5) . ?
C3 H3 0.9300 . ?
C3 C2 1.366(5) . ?
C3 C4 1.412(5) . ?
C9 C6 1.447(5) . ?
O8 N6 1.213(4) . ?
C12 C18 1.522(5) . ?
C2 H2 0.9300 . ?
C2 C1 1.410(4) . ?
N2 C7 1.360(4) . ?
N2 C1 1.335(4) . ?
C7 C4 1.407(4) . ?
C4 C5 1.435(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C14 H14D 0.9700 . ?
C14 C15 1.457(9) . ?
C14 C16A 1.495(13) . ?
C6 H6 0.9300 . ?
C6 C5 1.337(6) . ?
C5 H5 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.494(8) . ?
C13 C1 1.522(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.498(7) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.469(7) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16A H16C 0.9600 . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9600 . ?
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
Ho1 O9 N7 O10 0.2(3) . . . . ?
Ho1 O9 N7 O11 -179.2(3) . . . . ?
Ho1 O10 N7 O9 -0.2(3) . . . . ?
Ho1 O10 N7 O11 179.2(3) . . . . ?
Ho1 O1 C13 N1 -137.3(3) . . . . ?
Ho1 O1 C13 C1 43.7(4) . . . . ?
Ho1 O2 C18 N4 157.1(3) . . . . ?
Ho1 O2 C18 C12 -20.8(4) . . . . ?
Ho1 O6 N6 O7 5.0(3) . . . . ?
Ho1 O6 N6 O8 -175.1(3) . . . . ?
Ho1 N3 C8 C9 -178.0(2) . . . . ?
Ho1 N3 C8 C7 0.8(4) . . . . ?
Ho1 N3 C12 C11 176.5(2) . . . . ?
Ho1 N3 C12 C18 -0.8(3) . . . . ?
Ho1 O3 N5 O5 -169.2(3) . . . . ?
Ho1 O3 N5 O4 10.6(3) . . . . ?
Ho1 O7 N6 O6 -4.9(3) . . . . ?
Ho1 O7 N6 O8 175.3(4) . . . . ?
Ho1 N2 C7 C8 2.4(4) . . . . ?
Ho1 N2 C7 C4 179.6(2) . . . . ?
Ho1 N2 C1 C2 -179.2(3) . . . . ?
Ho1 N2 C1 C13 -5.3(3) . . . . ?
O1 C13 C1 C2 149.7(4) . . . . ?
O1 C13 C1 N2 -23.7(4) . . . . ?
N1 C13 C1 C2 -29.3(5) . . . . ?
N1 C13 C1 N2 157.3(3) . . . . ?
N3 C8 C9 C10 0.5(5) . . . . ?
N3 C8 C9 C6 179.4(3) . . . . ?
N3 C8 C7 N2 -2.0(4) . . . . ?
N3 C8 C7 C4 -179.4(3) . . . . ?
N3 C12 C18 O2 12.0(4) . . . . ?
N3 C12 C18 N4 -165.8(3) . . . . ?
C10 C11 C12 N3 2.3(5) . . . . ?
C10 C11 C12 C18 179.1(3) . . . . ?
C10 C9 C6 C5 178.9(4) . . . . ?
O3 N5 O4 Ho1 -10.8(3) . . . . ?
C8 N3 C12 C11 -2.5(5) . . . . ?
C8 N3 C12 C18 -179.9(3) . . . . ?
C8 C9 C6 C5 0.2(6) . . . . ?
C8 C7 C4 C3 176.9(3) . . . . ?
C8 C7 C4 C5 -0.4(5) . . . . ?
C11 C10 C9 C8 -0.7(6) . . . . ?
C11 C10 C9 C6 -179.5(4) . . . . ?
C11 C12 C18 O2 -165.1(3) . . . . ?
C11 C12 C18 N4 17.1(6) . . . . ?
C3 C2 C1 N2 -0.6(6) . . . . ?
C3 C2 C1 C13 -173.4(3) . . . . ?
C3 C4 C5 C6 -175.9(4) . . . . ?
C9 C10 C11 C12 -0.6(6) . . . . ?
C9 C8 C7 N2 176.8(3) . . . . ?
C9 C8 C7 C4 -0.5(5) . . . . ?
C9 C6 C5 C4 -1.1(7) . . . . ?
C12 N3 C8 C9 1.1(5) . . . . ?
C12 N3 C8 C7 179.9(3) . . . . ?
O5 N5 O4 Ho1 168.9(3) . . . . ?
C2 C3 C4 C7 -0.7(6) . . . . ?
C2 C3 C4 C5 176.4(4) . . . . ?
N2 C7 C4 C3 -0.3(5) . . . . ?
N2 C7 C4 C5 -177.5(3) . . . . ?
C7 C8 C9 C10 -178.3(3) . . . . ?
C7 C8 C9 C6 0.6(5) . . . . ?
C7 N2 C1 C2 -0.4(5) . . . . ?
C7 N2 C1 C13 173.5(3) . . . . ?
C7 C4 C5 C6 1.2(6) . . . . ?
C4 C3 C2 C1 1.1(6) . . . . ?
C14 N1 C16 C17 -74.5(5) . . . . ?
C14 N1 C13 O1 167.8(4) . . . . ?
C14 N1 C13 C1 -13.3(6) . . . . ?
C16 N1 C14 C15 111.3(5) . . . . ?
C16 N1 C14 C16A -86.8(8) . . . . ?
C16 N1 C13 O1 -1.5(6) . . . . ?
C16 N1 C13 C1 177.5(4) . . . . ?
C18 N4 C21 C22 -88.9(5) . . . . ?
C18 N4 C19 C20 -104.2(5) . . . . ?
C13 N1 C14 C15 -58.1(6) . . . . ?
C13 N1 C14 C16A 103.7(8) . . . . ?
C13 N1 C16 C17 96.0(5) . . . . ?
C1 N2 C7 C8 -176.4(3) . . . . ?
C1 N2 C7 C4 0.8(5) . . . . ?
C21 N4 C18 O2 2.1(5) . . . . ?
C21 N4 C18 C12 179.9(3) . . . . ?
C21 N4 C19 C20 86.9(5) . . . . ?
C19 N4 C18 O2 -166.6(4) . . . . ?
C19 N4 C18 C12 11.1(6) . . . . ?
C19 N4 C21 C22 81.2(5) . . . . ?
