#------------------------------------------------------------------------------
#$Date: 2025-08-04 09:03:09 +0200 (Mon 04 de Aug de 2025) $
#$Revision: 301442 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/63/7056363.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_7056363
loop_
_publ_author_name
'Wu, Yufan'
'Xu, Lixi'
'Shen, Yenan'
'Wang, Yang'
'Wang, Qiaochun'
_publ_section_title
;
 Helianthus-like Cucurbit[4]uril and Cucurbit[5]uril analogues
;
_journal_issue                   15
_journal_name_full               'New J. Chem.'
_journal_page_first              6991
_journal_page_last               6994
_journal_paper_doi               10.1039/C7NJ01595J
_journal_volume                  41
_journal_year                    2017
_chemical_formula_sum            'C44 H76 Ca2 Cl4 N16 O18'
_chemical_formula_weight         1339.16
_chemical_name_systematic
; 
 ? 
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-06-14 deposited with the CCDC.
2017-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.6460(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.6660(10)
_cell_length_b                   20.7418(16)
_cell_length_c                   11.6720(9)
_cell_measurement_reflns_used    7362
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      26.44
_cell_measurement_theta_min      2.26
_cell_volume                     2850.2(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_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  0.0202
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17930
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.439
_diffrn_reflns_theta_min         1.964
_exptl_absorpt_coefficient_mu    0.473
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.031
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         5836
_refine_ls_number_restraints     57
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[σ²(Fo²)+(0.0892P)²+1.9593P] 
 where P=(Fo²+2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1461
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4898
_reflns_number_total             5836
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7nj01595j2.cif
_cod_data_source_block           mo_40926aa
_cod_database_code               7056363
#BEGIN Tags that were not found in dictionaries:
_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_min   0.891
_shelx_estimated_absorpt_t_max   0.963
_shelxl_version_number           2013-2
#END Tags that were not found in dictionaries
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
Ca1 Ca 0.17521(4) 0.49477(2) 0.75795(4) 0.01792(14) Uani 1 1 d . . . . .
Cl1 Cl 0.42946(5) 0.42264(3) 0.58834(6) 0.03507(18) Uani 1 1 d . . . . .
Cl2 Cl 0.02087(6) 0.67977(3) 0.51027(6) 0.03703(19) Uani 1 1 d . . . . .
N1 N 0.26203(15) 0.43809(8) 1.13764(16) 0.0171(4) Uani 1 1 d . . . . .
N2 N 0.13739(15) 0.35886(8) 1.01882(16) 0.0172(4) Uani 1 1 d . . . . .
N3 N -0.04572(14) 0.36216(8) 0.84607(16) 0.0165(4) Uani 1 1 d . . . . .
N4 N -0.16638(15) 0.44132(9) 0.72337(16) 0.0180(4) Uani 1 1 d . . . . .
N5 N -0.16175(15) 0.55996(9) 0.71883(16) 0.0177(4) Uani 1 1 d . . . . .
N6 N -0.03516(15) 0.63735(9) 0.84044(16) 0.0173(4) Uani 1 1 d . . . . .
N7 N 0.14839(15) 0.63632(8) 1.01333(16) 0.0169(4) Uani 1 1 d . . . . .
N8 N 0.26829(15) 0.55631(8) 1.13438(16) 0.0168(4) Uani 1 1 d . . . . .
O1 O 0.22391(14) 0.42882(8) 0.93294(14) 0.0232(3) Uani 1 1 d . . . . .
O2 O 0.01463(13) 0.43118(8) 0.73228(15) 0.0231(3) Uani 1 1 d . . . . .
O3 O 0.02129(13) 0.56298(8) 0.73256(15) 0.0235(3) Uani 1 1 d . . . . .
O4 O 0.23837(14) 0.56619(8) 0.93079(14) 0.0226(3) Uani 1 1 d . . . . .
O5 O 0.37952(15) 0.47546(11) 0.81668(18) 0.0370(4) Uani 1 1 d . . . . .
H5A H 0.410(4) 0.457(2) 0.755(4) 0.092(14) Uiso 1 1 d . . . . .
H5B H 0.396(5) 0.439(3) 0.872(6) 0.139 Uiso 1 1 d . U . . .
O6 O 0.1749(2) 0.41893(12) 0.6074(2) 0.0495(6) Uani 1 1 d . . . . .
H6A H 0.231(4) 0.413(2) 0.579(4) 0.077(13) Uiso 1 1 d . . . . .
H6B H 0.129(5) 0.392(3) 0.575(5) 0.108(19) Uiso 1 1 d . . . . .
O7 O 0.21282(19) 0.57774(10) 0.6384(2) 0.0417(5) Uani 1 1 d D . . . .
H7A H 0.164(3) 0.6031(18) 0.593(3) 0.079(14) Uiso 1 1 d D . . . .
H7B H 0.2705(19) 0.5827(17) 0.625(3) 0.057(11) Uiso 1 1 d D . . . .
C1 C 0.20803(17) 0.40964(10) 1.02521(19) 0.0173(4) Uani 1 1 d . . . . .
C2 C 0.12514(18) 0.33174(10) 1.12909(19) 0.0172(4) Uani 1 1 d . . . . .
H2 H 0.1073 0.2853 1.1148 0.021 Uiso 1 1 calc R U . . .
C3 C 0.23849(17) 0.33879(10) 1.23815(19) 0.0184(4) Uani 1 1 d . . . . .
C4 C 0.25449(17) 0.41178(10) 1.25128(19) 0.0171(4) Uani 1 1 d . . . . .
H4 H 0.3270 0.4207 1.3203 0.021 Uiso 1 1 calc R U . . .
C5 C 0.06736(17) 0.33327(10) 0.89780(19) 0.0168(4) Uani 1 1 d . . . . .
H5C H 0.1067 0.3405 0.8406 0.020 Uiso 1 1 calc R U . . .
H5D H 0.0592 0.2866 0.9048 0.020 Uiso 1 1 calc R U . . .
C6 C -0.06205(18) 0.41261(10) 0.76582(19) 0.0168(4) Uani 1 1 d . . . . .
C7 C -0.26089(17) 0.41583(10) 0.75329(19) 0.0172(4) Uani 1 1 d . . . . .
H7 H -0.3325 0.4256 0.6837 0.021 Uiso 1 1 calc R U . . .
C8 C -0.25001(17) 0.34275(10) 0.76740(19) 0.0181(4) Uani 1 1 d . . . . .
C9 C -0.13757(17) 0.33447(10) 0.87708(19) 0.0166(4) Uani 1 1 d . . . . .
H9 H -0.1228 0.2878 0.8926 0.020 Uiso 1 1 calc R U . . .
C10 C -0.18168(19) 0.49964(9) 0.6487(2) 0.0177(4) Uani 1 1 d . . . . .
H10A H -0.2594 0.5001 0.5875 0.021 Uiso 1 1 calc R U . . .
H10B H -0.1298 0.4978 0.6039 0.021 Uiso 1 1 calc R U . . .
C11 C -0.05511(18) 0.58549(10) 0.76300(19) 0.0174(4) Uani 1 1 d . . . . .
C12 C 0.08028(17) 0.66297(10) 0.89226(19) 0.0169(4) Uani 1 1 d . . . . .
H12A H 0.0763 0.7099 0.8995 0.020 Uiso 1 1 calc R U . . .
H12B H 0.1188 0.6539 0.8350 0.020 Uiso 1 1 calc R U . . .
C13 C 0.21864(17) 0.58508(10) 1.02165(19) 0.0171(4) Uani 1 1 d . . . . .
C14 C 0.33009(18) 0.49596(9) 1.1437(2) 0.0177(4) Uani 1 1 d . . . . .
H14A H 0.3955 0.4957 1.2217 0.021 Uiso 1 1 calc R U . . .
H14B H 0.3592 0.4943 1.0767 0.021 Uiso 1 1 calc R U . . .
C15 C 0.33685(19) 0.30477(11) 1.2131(2) 0.0240(5) Uani 0.603(14) 1 d . . P A 1
H15A H 0.3073 0.2802 1.1360 0.029 Uiso 0.603(14) 1 calc R U P A 1
H15B H 0.3914 0.3366 1.2063 0.029 Uiso 0.603(14) 1 calc R U P A 1
C16 C 0.3932(5) 0.2602(4) 1.3203(6) 0.0361(18) Uani 0.603(14) 1 d . U P A 1
H16A H 0.4534 0.2825 1.3868 0.043 Uiso 0.603(14) 1 calc R U P A 1
H16B H 0.4257 0.2225 1.2948 0.043 Uiso 0.603(14) 1 calc R U P A 1
C17 C 0.2949(10) 0.2406(6) 1.3612(12) 0.033(2) Uani 0.603(14) 1 d . U P A 1
H17A H 0.2444 0.2092 1.3044 0.040 Uiso 0.603(14) 1 calc R U P A 1
H17B H 0.3233 0.2228 1.4449 0.040 Uiso 0.603(14) 1 calc R U P A 1
C18 C 0.2354(2) 0.30565(11) 1.3557(2) 0.0237(5) Uani 0.603(14) 1 d . . P A 1
H18A H 0.2758 0.3316 1.4291 0.028 Uiso 0.603(14) 1 calc R U P A 1
H18B H 0.1570 0.2993 1.3500 0.028 Uiso 0.603(14) 1 calc R U P A 1
C19 C -0.2482(2) 0.30837(11) 0.6505(2) 0.0236(5) Uani 0.626(16) 1 d . . P B 1
H19A H -0.2929 0.3323 0.5759 0.028 Uiso 0.626(16) 1 calc R U P B 1
H19B H -0.1703 0.3037 0.6533 0.028 Uiso 0.626(16) 1 calc R U P B 1
C20 C -0.3014(8) 0.2425(4) 0.6534(9) 0.0298(17) Uani 0.626(16) 1 d . U P B 1
H20A H -0.3290 0.2222 0.5718 0.036 Uiso 0.626(16) 1 calc R U P B 1
H20B H -0.2471 0.2135 0.7126 0.036 Uiso 0.626(16) 1 calc R U P B 1
C21 C -0.3994(6) 0.2596(3) 0.6940(7) 0.0344(16) Uani 0.626(16) 1 d . U P B 1
H21A H -0.4641 0.2767 0.6250 0.041 Uiso 0.626(16) 1 calc R U P B 1
H21B H -0.4243 0.2218 0.7278 0.041 Uiso 0.626(16) 1 calc R U P B 1
C22 C -0.34954(19) 0.31067(11) 0.7927(2) 0.0230(5) Uani 0.626(16) 1 d . . P B 1
H22A H -0.3221 0.2909 0.8747 0.028 Uiso 0.626(16) 1 calc R U P B 1
H22B H -0.4073 0.3429 0.7890 0.028 Uiso 0.626(16) 1 calc R U P B 1
C15' C 0.33685(19) 0.30477(11) 1.2131(2) 0.0240(5) Uani 0.397(14) 1 d . . P A 2
H15C H 0.3209 0.3018 1.1245 0.029 Uiso 0.397(14) 1 calc R U P A 2
H15D H 0.4088 0.3277 1.2530 0.029 Uiso 0.397(14) 1 calc R U P A 2
C16' C 0.3404(11) 0.2390(4) 1.2687(12) 0.045(3) Uani 0.397(14) 1 d . U P A 2
H16C H 0.2808 0.2112 1.2136 0.055 Uiso 0.397(14) 1 calc R U P A 2
H16D H 0.4144 0.2185 1.2861 0.055 Uiso 0.397(14) 1 calc R U P A 2
C17' C 0.3207(17) 0.2524(11) 1.385(2) 0.043(4) Uani 0.397(14) 1 d . U P A 2
H17C H 0.2915 0.2139 1.4125 0.052 Uiso 0.397(14) 1 calc R U P A 2
H17D H 0.3916 0.2655 1.4512 0.052 Uiso 0.397(14) 1 calc R U P A 2
C18' C 0.2354(2) 0.30565(11) 1.3557(2) 0.0237(5) Uani 0.397(14) 1 d . . P A 2
H18C H 0.2550 0.3365 1.4240 0.028 Uiso 0.397(14) 1 calc R U P A 2
H18D H 0.1595 0.2884 1.3409 0.028 Uiso 0.397(14) 1 calc R U P A 2
C19' C -0.2482(2) 0.30837(11) 0.6505(2) 0.0236(5) Uani 0.374(16) 1 d . . P B 2
H19C H -0.2702 0.3384 0.5807 0.028 Uiso 0.374(16) 1 calc R U P B 2
H19D H -0.1719 0.2920 0.6644 0.028 Uiso 0.374(16) 1 calc R U P B 2
C20' C -0.3305(14) 0.2545(10) 0.6248(16) 0.052(5) Uani 0.374(16) 1 d . U P B 2
H20C H -0.2992 0.2156 0.6015 0.062 Uiso 0.374(16) 1 calc R U P B 2
H20D H -0.4015 0.2658 0.5575 0.062 Uiso 0.374(16) 1 calc R U P B 2
C21' C -0.3511(13) 0.2433(5) 0.7422(14) 0.044(3) Uani 0.374(16) 1 d . U P B 2
H21C H -0.2911 0.2165 0.7997 0.053 Uiso 0.374(16) 1 calc R U P B 2
H21D H -0.4247 0.2224 0.7255 0.053 Uiso 0.374(16) 1 calc R U P B 2
C22' C -0.34954(19) 0.31067(11) 0.7927(2) 0.0230(5) Uani 0.374(16) 1 d . . P B 2
H22C H -0.3353 0.3097 0.8811 0.028 Uiso 0.374(16) 1 calc R U P B 2
H22D H -0.4213 0.3332 0.7494 0.028 Uiso 0.374(16) 1 calc R U P B 2
O8 O 0.5102(2) 0.40822(14) 0.0373(3) 0.0639(7) Uani 1 1 d D . . . .
H8A H 0.573(3) 0.397(2) 0.032(4) 0.096 Uiso 1 1 d D U . . .
H8B H 0.522(4) 0.407(2) 0.114(2) 0.096 Uiso 1 1 d D U . . .
O9 O 0.42663(19) 0.57545(11) 0.5935(2) 0.0422(5) Uani 1 1 d D . . . .
H9A H 0.457(3) 0.5885(14) 0.553(3) 0.044(10) Uiso 1 1 d D . . . .
H9B H 0.425(3) 0.5365(9) 0.594(3) 0.061(12) Uiso 1 1 d D . . . .
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ca Ca 0.2262 0.3064 '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
O3 Ca1 O1 113.75(6) . .
O3 Ca1 O2 71.41(6) . .
O1 Ca1 O2 73.78(6) . .
O3 Ca1 O6 122.51(8) . .
O1 Ca1 O6 100.82(8) . .
O2 Ca1 O6 76.53(7) . .
O3 Ca1 O7 79.95(7) . .
O1 Ca1 O7 152.96(7) . .
O2 Ca1 O7 133.21(7) . .
O6 Ca1 O7 89.48(9) . .
O3 Ca1 O4 74.68(5) . .
O1 Ca1 O4 74.20(6) . .
O2 Ca1 O4 117.40(6) . .
O6 Ca1 O4 161.92(7) . .
O7 Ca1 O4 88.26(7) . .
O3 Ca1 O5 151.49(7) . .
O1 Ca1 O5 75.51(7) . .
O2 Ca1 O5 135.93(7) . .
O6 Ca1 O5 79.09(8) . .
O7 Ca1 O5 82.11(8) . .
O4 Ca1 O5 82.83(6) . .
C1 N1 C14 118.44(17) . .
C1 N1 C4 121.94(17) . .
C14 N1 C4 119.61(17) . .
C1 N2 C5 118.96(17) . .
C1 N2 C2 121.86(17) . .
C5 N2 C2 119.09(17) . .
C6 N3 C9 122.57(17) . .
C6 N3 C5 118.28(17) . .
C9 N3 C5 119.08(17) . .
C6 N4 C10 118.37(18) . .
C6 N4 C7 121.55(18) . .
C10 N4 C7 120.07(17) . .
C11 N5 C10 119.06(18) . .
C11 N5 C4 121.61(17) . 3_567
C10 N5 C4 119.12(17) . 3_567
C11 N6 C12 118.20(17) . .
C11 N6 C2 122.38(17) . 3_567
C12 N6 C2 119.41(17) . 3_567
C13 N7 C12 119.88(17) . .
C13 N7 C9 121.81(17) . 3_567
C12 N7 C9 118.30(16) . 3_567
C13 N8 C14 119.28(17) . .
C13 N8 C7 121.96(17) . 3_567
C14 N8 C7 118.75(17) . 3_567
C1 O1 Ca1 151.00(15) . .
C6 O2 Ca1 151.63(15) . .
C11 O3 Ca1 153.52(15) . .
C13 O4 Ca1 143.87(15) . .
Ca1 O5 H5A 120(3) . .
Ca1 O5 H5B 105(4) . .
H5A O5 H5B 98(4) . .
Ca1 O6 H6A 126(3) . .
Ca1 O6 H6B 129(4) . .
H6A O6 H6B 106(4) . .
Ca1 O7 H7A 124(3) . .
Ca1 O7 H7B 127(2) . .
H7A O7 H7B 108(3) . .
O1 C1 N2 121.06(19) . .
O1 C1 N1 120.91(19) . .
N2 C1 N1 118.03(18) . .
N6 C2 N2 112.98(16) 3_567 .
N6 C2 C3 109.35(17) 3_567 .
N2 C2 C3 108.81(17) . .
N6 C2 H2 108.5 3_567 .
N2 C2 H2 108.5 . .
C3 C2 H2 108.5 . .
C4 C3 C2 103.09(16) . .
C4 C3 C18 113.38(18) . .
C2 C3 C18 111.80(18) . .
C4 C3 C15 112.57(18) . .
C2 C3 C15 111.79(18) . .
C18 C3 C15 104.46(17) . .
N5 C4 N1 113.01(16) 3_567 .
N5 C4 C3 109.40(17) 3_567 .
N1 C4 C3 109.14(17) . .
N5 C4 H4 108.4 3_567 .
N1 C4 H4 108.4 . .
C3 C4 H4 108.4 . .
N3 C5 N2 113.76(16) . .
N3 C5 H5C 108.8 . .
N2 C5 H5C 108.8 . .
N3 C5 H5D 108.8 . .
N2 C5 H5D 108.8 . .
H5C C5 H5D 107.7 . .
O2 C6 N4 121.20(19) . .
O2 C6 N3 121.17(19) . .
N4 C6 N3 117.63(18) . .
N4 C7 N8 113.48(16) . 3_567
N4 C7 C8 109.60(17) . .
N8 C7 C8 109.14(17) 3_567 .
N4 C7 H7 108.2 . .
N8 C7 H7 108.2 3_567 .
C8 C7 H7 108.2 . .
C7 C8 C9 102.74(16) . .
C7 C8 C22 113.61(18) . .
C9 C8 C22 111.34(17) . .
C7 C8 C19 113.13(18) . .
C9 C8 C19 111.92(17) . .
C22 C8 C19 104.36(17) . .
N3 C9 N7 113.17(16) . 3_567
N3 C9 C8 109.21(17) . .
N7 C9 C8 108.97(16) 3_567 .
N3 C9 H9 108.5 . .
N7 C9 H9 108.5 3_567 .
C8 C9 H9 108.5 . .
N4 C10 N5 114.59(18) . .
N4 C10 H10A 108.6 . .
N5 C10 H10A 108.6 . .
N4 C10 H10B 108.6 . .
N5 C10 H10B 108.6 . .
H10A C10 H10B 107.6 . .
O3 C11 N5 121.01(19) . .
O3 C11 N6 120.85(19) . .
N5 C11 N6 118.13(18) . .
N6 C12 N7 113.92(16) . .
N6 C12 H12A 108.8 . .
N7 C12 H12A 108.8 . .
N6 C12 H12B 108.8 . .
N7 C12 H12B 108.8 . .
H12A C12 H12B 107.7 . .
O4 C13 N7 121.10(19) . .
O4 C13 N8 121.25(19) . .
N7 C13 N8 117.63(18) . .
N8 C14 N1 114.18(18) . .
N8 C14 H14A 108.7 . .
N1 C14 H14A 108.7 . .
N8 C14 H14B 108.7 . .
N1 C14 H14B 108.7 . .
H14A C14 H14B 107.6 . .
C16 C15 C3 106.8(2) . .
C16 C15 H15A 110.4 . .
C3 C15 H15A 110.4 . .
C16 C15 H15B 110.4 . .
C3 C15 H15B 110.4 . .
H15A C15 H15B 108.6 . .
C15 C16 C17 103.3(6) . .
C15 C16 H16A 111.1 . .
C17 C16 H16A 111.1 . .
C15 C16 H16B 111.1 . .
C17 C16 H16B 111.1 . .
H16A C16 H16B 109.1 . .
C18 C17 C16 101.2(8) . .
C18 C17 H17A 111.5 . .
C16 C17 H17A 111.5 . .
C18 C17 H17B 111.5 . .
C16 C17 H17B 111.5 . .
H17A C17 H17B 109.3 . .
C17 C18 C3 104.8(5) . .
C17 C18 H18A 110.8 . .
C3 C18 H18A 110.8 . .
C17 C18 H18B 110.8 . .
C3 C18 H18B 110.8 . .
H18A C18 H18B 108.9 . .
C20 C19 C8 104.0(4) . .
C20 C19 H19A 111.0 . .
C8 C19 H19A 111.0 . .
C20 C19 H19B 111.0 . .
C8 C19 H19B 111.0 . .
H19A C19 H19B 109.0 . .
C21 C20 C19 102.4(6) . .
C21 C20 H20A 111.3 . .
C19 C20 H20A 111.3 . .
C21 C20 H20B 111.3 . .
C19 C20 H20B 111.3 . .
H20A C20 H20B 109.2 . .
C22 C21 C20 103.8(5) . .
C22 C21 H21A 111.0 . .
C20 C21 H21A 111.0 . .
C22 C21 H21B 111.0 . .
C20 C21 H21B 111.0 . .
H21A C21 H21B 109.0 . .
C21 C22 C8 107.2(2) . .
C21 C22 H22A 110.3 . .
C8 C22 H22A 110.3 . .
C21 C22 H22B 110.3 . .
C8 C22 H22B 110.3 . .
H22A C22 H22B 108.5 . .
C17' C16' H16C 111.0 . .
C17' C16' H16D 111.0 . .
H16C C16' H16D 109.0 . .
C16' C17' H17C 110.6 . .
C16' C17' H17D 110.6 . .
H17C C17' H17D 108.7 . .
C21' C20' H20C 110.5 . .
C21' C20' H20D 110.5 . .
H20C C20' H20D 108.7 . .
C20' C21' H21C 111.1 . .
C20' C21' H21D 111.1 . .
H21C C21' H21D 109.1 . .
H8A O8 H8B 105(3) . .
H9A O9 H9B 112(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ca1 O3 2.3376(16) .
Ca1 O1 2.3439(16) .
Ca1 O2 2.3487(16) .
Ca1 O6 2.358(2) .
Ca1 O7 2.3722(19) .
Ca1 O4 2.3903(16) .
Ca1 O5 2.4532(19) .
N1 C1 1.370(3) .
N1 C14 1.464(3) .
N1 C4 1.470(3) .
N2 C1 1.366(3) .
N2 C5 1.463(3) .
N2 C2 1.464(3) .
N3 C6 1.368(3) .
N3 C9 1.458(3) .
N3 C5 1.462(3) .
N4 C6 1.365(3) .
N4 C10 1.461(3) .
N4 C7 1.464(3) .
N5 C11 1.363(3) .
N5 C10 1.465(3) .
N5 C4 1.465(3) 3_567
N6 C11 1.367(3) .
N6 C12 1.461(3) .
N6 C2 1.461(3) 3_567
N7 C13 1.366(3) .
N7 C12 1.465(3) .
N7 C9 1.467(3) 3_567
N8 C13 1.368(3) .
N8 C14 1.459(3) .
N8 C7 1.467(3) 3_567
O1 C1 1.232(3) .
O2 C6 1.235(3) .
O3 C11 1.239(3) .
O4 C13 1.239(3) .
O5 H5A 1.01(5) .
O5 H5B 0.97(7) .
O6 H6A 0.89(5) .
O6 H6B 0.80(6) .
O7 H7A 0.836(18) .
O7 H7B 0.810(18) .
C2 N6 1.461(3) 3_567
C2 C3 1.535(3) .
C2 H2 0.9900 .
C3 C4 1.528(3) .
C3 C18 1.548(3) .
C3 C15 1.551(3) .
C4 N5 1.466(3) 3_567
C4 H4 0.9900 .
C5 H5C 0.9800 .
C5 H5D 0.9800 .
C7 N8 1.467(3) 3_567
C7 C8 1.525(3) .
C7 H7 0.9900 .
C8 C9 1.533(3) .
C8 C22 1.547(3) .
C8 C19 1.548(3) .
C9 N7 1.467(3) 3_567
C9 H9 0.9900 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C15 C16 1.507(5) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C16 C17 1.543(12) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C17 C18 1.535(12) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C19 C20 1.530(9) .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C20 C21 1.525(10) .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C21 C22 1.520(5) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C16' C17' 1.50(3) .
C16' H16C 0.9800 .
C16' H16D 0.9800 .
C17' H17C 0.9800 .
C17' H17D 0.9800 .
C20' C21' 1.50(2) .
C20' H20C 0.9800 .
C20' H20D 0.9800 .
C21' H21C 0.9800 .
C21' H21D 0.9800 .
O8 H8A 0.857(19) .
O8 H8B 0.847(19) .
O9 H9A 0.765(17) .
O9 H9B 0.809(18) .
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
O9 H9B Cl1 0.809(18) 2.363(19) 3.171(3) 176(3) .
O9 H9A Cl1 0.765(17) 2.56(2) 3.268(2) 154(3) 3_666
O8 H8A O4 0.857(19) 2.39(4) 3.112(3) 142(4) 3_666
C9 H9 Cl2 0.99 2.63 3.574(2) 160.6 2_546
C5 H5D Cl2 0.98 2.77 3.664(2) 152.2 2_546
C2 H2 Cl2 0.99 2.79 3.713(2) 154.5 2_546
O7 H7B O9 0.810(18) 2.144(19) 2.942(3) 169(3) .
O7 H7A Cl2 0.836(18) 2.33(2) 3.153(2) 167(4) .
O6 H6B Cl2 0.80(6) 2.32(6) 3.117(2) 172(5) 3_566
O6 H6A Cl1 0.89(5) 2.48(5) 3.313(2) 154(4) .
O5 H5B O8 0.97(7) 2.04(7) 2.859(3) 141(5) 1_556
O5 H5A Cl1 1.01(5) 2.17(5) 3.154(2) 165(4) .
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_4
Ca1 O1 C1 N2 89.3(3) . .
Ca1 O1 C1 N1 -91.7(3) . .
C5 N2 C1 O1 -9.0(3) . .
C2 N2 C1 O1 174.51(19) . .
C5 N2 C1 N1 171.94(17) . .
C2 N2 C1 N1 -4.6(3) . .
C14 N1 C1 O1 6.1(3) . .
C4 N1 C1 O1 -173.14(19) . .
C14 N1 C1 N2 -174.78(18) . .
C4 N1 C1 N2 5.9(3) . .
C1 N2 C2 N6 89.7(2) . 3_567
C5 N2 C2 N6 -86.8(2) . 3_567
C1 N2 C2 C3 -31.9(2) . .
C5 N2 C2 C3 151.58(17) . .
N6 C2 C3 C4 -60.8(2) 3_567 .
N2 C2 C3 C4 63.0(2) . .
N6 C2 C3 C18 61.3(2) 3_567 .
N2 C2 C3 C18 -174.88(17) . .
N6 C2 C3 C15 178.01(17) 3_567 .
N2 C2 C3 C15 -58.2(2) . .
C1 N1 C4 N5 -92.4(2) . 3_567
C14 N1 C4 N5 88.3(2) . 3_567
C1 N1 C4 C3 29.6(3) . .
C14 N1 C4 C3 -149.71(18) . .
C2 C3 C4 N5 62.3(2) . 3_567
C18 C3 C4 N5 -58.7(2) . 3_567
C15 C3 C4 N5 -177.04(16) . 3_567
C2 C3 C4 N1 -61.8(2) . .
C18 C3 C4 N1 177.16(16) . .
C15 C3 C4 N1 58.8(2) . .
C6 N3 C5 N2 95.5(2) . .
C9 N3 C5 N2 -87.3(2) . .
C1 N2 C5 N3 -92.4(2) . .
C2 N2 C5 N3 84.2(2) . .
Ca1 O2 C6 N4 93.2(3) . .
Ca1 O2 C6 N3 -87.4(3) . .
C10 N4 C6 O2 -7.3(3) . .
C7 N4 C6 O2 174.10(19) . .
C10 N4 C6 N3 173.27(17) . .
C7 N4 C6 N3 -5.3(3) . .
C9 N3 C6 O2 -173.10(18) . .
C5 N3 C6 O2 4.0(3) . .
C9 N3 C6 N4 6.3(3) . .
C5 N3 C6 N4 -176.59(17) . .
C6 N4 C7 N8 90.8(2) . 3_567
C10 N4 C7 N8 -87.8(2) . 3_567
C6 N4 C7 C8 -31.5(3) . .
C10 N4 C7 C8 149.95(18) . .
N4 C7 C8 C9 62.5(2) . .
N8 C7 C8 C9 -62.3(2) 3_567 .
N4 C7 C8 C22 -177.06(16) . .
N8 C7 C8 C22 58.1(2) 3_567 .
N4 C7 C8 C19 -58.3(2) . .
N8 C7 C8 C19 176.86(16) 3_567 .
C6 N3 C9 N7 -92.2(2) . 3_567
C5 N3 C9 N7 90.7(2) . 3_567
C6 N3 C9 C8 29.3(3) . .
C5 N3 C9 C8 -147.69(17) . .
C7 C8 C9 N3 -61.3(2) . .
C22 C8 C9 N3 176.75(17) . .
C19 C8 C9 N3 60.4(2) . .
C7 C8 C9 N7 62.8(2) . 3_567
C22 C8 C9 N7 -59.2(2) . 3_567
C19 C8 C9 N7 -175.54(17) . 3_567
C6 N4 C10 N5 -92.0(2) . .
C7 N4 C10 N5 86.7(2) . .
C11 N5 C10 N4 89.9(2) . .
C4 N5 C10 N4 -84.8(2) 3_567 .
Ca1 O3 C11 N5 -92.3(4) . .
Ca1 O3 C11 N6 88.7(4) . .
C10 N5 C11 O3 8.7(3) . .
C4 N5 C11 O3 -176.65(19) 3_567 .
C10 N5 C11 N6 -172.29(17) . .
C4 N5 C11 N6 2.3(3) 3_567 .
C12 N6 C11 O3 -3.7(3) . .
C2 N6 C11 O3 175.22(19) 3_567 .
C12 N6 C11 N5 177.29(17) . .
C2 N6 C11 N5 -3.8(3) 3_567 .
C11 N6 C12 N7 -93.5(2) . .
C2 N6 C12 N7 87.6(2) 3_567 .
C13 N7 C12 N6 95.1(2) . .
C9 N7 C12 N6 -84.1(2) 3_567 .
Ca1 O4 C13 N7 -89.8(3) . .
Ca1 O4 C13 N8 91.6(3) . .
C12 N7 C13 O4 10.3(3) . .
C9 N7 C13 O4 -170.51(18) 3_567 .
C12 N7 C13 N8 -171.14(17) . .
C9 N7 C13 N8 8.1(3) 3_567 .
C14 N8 C13 O4 -10.4(3) . .
C7 N8 C13 O4 169.91(19) 3_567 .
C14 N8 C13 N7 171.01(18) . .
C7 N8 C13 N7 -8.7(3) 3_567 .
C13 N8 C14 N1 -94.1(2) . .
C7 N8 C14 N1 85.6(2) 3_567 .
C1 N1 C14 N8 92.8(2) . .
C4 N1 C14 N8 -87.9(2) . .
C4 C3 C15 C16 117.5(4) . .
C2 C3 C15 C16 -127.0(4) . .
C18 C3 C15 C16 -5.9(4) . .
C3 C15 C16 C17 30.7(8) . .
C15 C16 C17 C18 -43.4(9) . .
C16 C17 C18 C3 39.9(8) . .
C4 C3 C18 C17 -144.3(5) . .
C2 C3 C18 C17 99.7(5) . .
C15 C3 C18 C17 -21.4(5) . .
C7 C8 C19 C20 -149.9(4) . .
C9 C8 C19 C20 94.6(4) . .
C22 C8 C19 C20 -25.9(4) . .
C8 C19 C20 C21 41.3(7) . .
C19 C20 C21 C22 -40.5(8) . .
C20 C21 C22 C8 24.5(7) . .
C7 C8 C22 C21 124.6(4) . .
C9 C8 C22 C21 -120.0(4) . .
C19 C8 C22 C21 0.9(4) . .
