# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_aemPb
_database_code_depnum_ccdc_archive 'CCDC 2032603'
loop_
_audit_author_name
_audit_author_address
'Andres De Blas'
;University of A Coruna
Spain
;
_audit_update_record             
;
2020-09-17 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;

_audit_creation_date             2019-05-21T14:04:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C21  H33  N5  O4  Cl  Pb1 (ClO4)'
_chemical_formula_sum            'C21 H33 Cl2 N5 O8 Pb'
_chemical_formula_weight         761.61

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   11.2878(4)
_cell_length_b                   19.5609(8)
_cell_length_c                   12.4512(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.307(2)
_cell_angle_gamma                90
_cell_volume                     2744.64(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9569
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.17
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.485
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.172
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1496

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    6.394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.276
_exptl_absorpt_correction_T_max  0.746
_shelx_estimated_absorpt_T_min   0.147
_shelx_estimated_absorpt_T_max   0.406

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Fine focus'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector                 CCD
_diffrn_measurement_device       'Bruker X8 APEX'
_diffrn_measurement_device_type  'Bruker X8 APEX'
_diffrn_measurement_method       'Omega  and  phi rotation with narrow frames'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_number            70491
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.082
_diffrn_reflns_theta_max         27.231
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_Friedel_coverage         0
_reflns_number_total             6083
_reflns_number_gt                5645
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       'SAINT V3.37A (Bruker, 2015) in Apex2 suite'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0269P)²+11.9523P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6083
_refine_ls_number_parameters     341
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0735
_refine_ls_wR_factor_gt          0.0726
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.528
_refine_diff_density_min         -2.5
_refine_diff_density_rms         0.128

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Pb1 Pb 0.84323(2) 0.35379(2) 0.64171(2) 0.01747(6) Uani 1 1 d . . . . .
C1 C 0.7323(4) 0.2377(2) 0.5381(3) 0.0186(8) Uani 1 1 d . . . . .
C2 C 0.6518(4) 0.1818(2) 0.4907(3) 0.0179(8) Uani 1 1 d . . . . .
C3 C 0.6995(4) 0.1283(2) 0.4355(4) 0.0262(10) Uani 1 1 d . . . . .
H3 H 0.782458 0.125915 0.426851 0.031 Uiso 1 1 calc R U . . .
C4 C 0.6239(5) 0.0778(2) 0.3926(4) 0.0310(11) Uani 1 1 d . . . . .
H4 H 0.653808 0.041456 0.351479 0.037 Uiso 1 1 calc R U . . .
C5 C 0.5041(4) 0.0817(2) 0.4110(4) 0.0243(9) Uani 1 1 d . . . . .
H5 H 0.450629 0.047249 0.384805 0.029 Uiso 1 1 calc R U . . .
C6 C 0.4641(4) 0.1372(2) 0.4689(3) 0.0176(8) Uani 1 1 d . . . . .
C7 C 0.3321(4) 0.1423(2) 0.4856(3) 0.0183(8) Uani 1 1 d . . . . .
H7A H 0.288488 0.145628 0.41449 0.022 Uiso 1 1 calc R U . . .
H7B H 0.306097 0.099848 0.520603 0.022 Uiso 1 1 calc R U . . .
C8 C 0.1691(3) 0.2155(2) 0.5402(3) 0.0163(8) Uani 1 1 d . . . . .
H8A H 0.147035 0.245494 0.599964 0.02 Uiso 1 1 calc R U . . .
H8B H 0.126173 0.171738 0.547004 0.02 Uiso 1 1 calc R U . . .
C9 C 0.1284(4) 0.2489(2) 0.4343(3) 0.0180(8) Uani 1 1 d . . . . .
H9A H 0.149731 0.218634 0.374734 0.022 Uiso 1 1 calc R U . . .
H9B H 0.040834 0.252831 0.431174 0.022 Uiso 1 1 calc R U . . .
C10 C 0.1315(4) 0.3421(2) 0.3089(3) 0.0193(8) Uani 1 1 d . . . . .
H10A H 0.047509 0.355611 0.313963 0.023 Uiso 1 1 calc R U . . .
H10B H 0.133844 0.304014 0.256677 0.023 Uiso 1 1 calc R U . . .
C11 C 0.2004(4) 0.4026(2) 0.2667(4) 0.0196(8) Uani 1 1 d . . . . .
H11A H 0.162982 0.416706 0.196282 0.023 Uiso 1 1 calc R U . . .
H11B H 0.194068 0.441473 0.316932 0.023 Uiso 1 1 calc R U . . .
C12 C 0.3309(4) 0.3881(2) 0.2531(3) 0.0191(8) Uani 1 1 d . . . . .
H12A H 0.338442 0.354486 0.194339 0.023 Uiso 1 1 calc R U . . .
H12B H 0.371069 0.430716 0.232653 0.023 Uiso 1 1 calc R U . . .
C13 C 0.4159(4) 0.4158(2) 0.4360(3) 0.0182(8) Uani 1 1 d . . . . .
H13A H 0.346117 0.44632 0.437339 0.022 Uiso 1 1 calc R U . . .
H13B H 0.483726 0.443325 0.413297 0.022 Uiso 1 1 calc R U . . .
C14 C 0.4449(4) 0.3884(2) 0.5485(3) 0.0182(8) Uani 1 1 d . . . . .
H14A H 0.523914 0.366353 0.550068 0.022 Uiso 1 1 calc R U . . .
H14B H 0.450294 0.427466 0.599117 0.022 Uiso 1 1 calc R U . . .
C15 C 0.4093(4) 0.3131(2) 0.6928(3) 0.0175(8) Uani 1 1 d . . . . .
H15A H 0.411288 0.350964 0.745598 0.021 Uiso 1 1 calc R U . . .
H15B H 0.491997 0.297949 0.68479 0.021 Uiso 1 1 calc R U . . .
C16 C 0.3384(4) 0.2537(2) 0.7366(3) 0.0173(8) Uani 1 1 d . . . . .
H16A H 0.370927 0.242776 0.810114 0.021 Uiso 1 1 calc R U . . .
H16B H 0.255147 0.268576 0.742105 0.021 Uiso 1 1 calc R U . . .
C17 C 0.3391(4) 0.1893(2) 0.6693(3) 0.0179(8) Uani 1 1 d . . . . .
H17A H 0.285387 0.155239 0.699664 0.021 Uiso 1 1 calc R U . . .
H17B H 0.420181 0.169798 0.673498 0.021 Uiso 1 1 calc R U . . .
C18 C 0.1528(3) 0.3678(2) 0.5002(3) 0.0176(8) Uani 1 1 d . . . . .
H18A H 0.072665 0.358044 0.524714 0.021 Uiso 1 1 calc R U . . .
H18B H 0.15029 0.413679 0.466746 0.021 Uiso 1 1 calc R U . . .
C19 C 0.2407(4) 0.3701(2) 0.6001(3) 0.0175(8) Uani 1 1 d . . . . .
H19A H 0.252493 0.418472 0.621461 0.021 Uiso 1 1 calc R U . . .
H19B H 0.203846 0.346461 0.660034 0.021 Uiso 1 1 calc R U . . .
C20 C 0.4963(3) 0.3191(2) 0.3334(4) 0.0180(8) Uani 1 1 d . . . . .
H20A H 0.54217 0.309651 0.402011 0.022 Uiso 1 1 calc R U . . .
H20B H 0.547691 0.345401 0.286688 0.022 Uiso 1 1 calc R U . . .
C21 C 0.4619(4) 0.2515(2) 0.2787(3) 0.0160(8) Uani 1 1 d . . . . .
N1 N 0.5343(3) 0.18690(19) 0.5066(3) 0.0179(7) Uani 1 1 d . . . . .
N2 N 0.3004(3) 0.20176(18) 0.5522(3) 0.0150(7) Uani 1 1 d . . . . .
N3 N 0.1792(3) 0.31732(18) 0.4170(3) 0.0160(7) Uani 1 1 d . . . . .
N4 N 0.3903(3) 0.36033(18) 0.3552(3) 0.0157(7) Uani 1 1 d . . . . .
N5 N 0.3589(3) 0.33906(17) 0.5866(3) 0.0151(7) Uani 1 1 d . . . . .
O1 O 0.6817(3) 0.28858(16) 0.5806(3) 0.0212(6) Uani 1 1 d . . . . .
O2 O 0.8411(3) 0.23086(17) 0.5358(3) 0.0237(7) Uani 1 1 d . . . . .
O3 O 0.3540(2) 0.23253(15) 0.2806(2) 0.0180(6) Uani 1 1 d . . . . .
O4 O 0.5408(3) 0.21908(16) 0.2357(2) 0.0207(6) Uani 1 1 d . . . . .
Cl1 Cl 0.68797(9) 0.42290(5) 0.75586(8) 0.0193(2) Uani 1 1 d . . . . .
H2 H 0.336(5) 0.235(3) 0.534(4) 0.023 Uiso 1 1 d . U . . .
H4A H 0.345(5) 0.336(3) 0.381(4) 0.023 Uiso 1 1 d . U . . .
O5 O 0.7770(5) 0.4657(2) 0.4887(3) 0.0612(15) Uani 1 1 d . . . . .
O6 O 0.8363(4) 0.36775(17) 0.4021(3) 0.0332(8) Uani 1 1 d . . . . .
O7 O 0.9020(4) 0.4751(2) 0.3484(5) 0.0609(14) Uani 1 1 d . . . . .
O8 O 0.7066(4) 0.4457(2) 0.3120(4) 0.0601(14) Uani 1 1 d . . . . .
Cl2 Cl 0.80621(10) 0.43896(5) 0.38767(8) 0.0219(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Pb1 O1 2.317(3) . y
Pb1 O3 2.415(3) 4_666 y
Pb1 Cl1 2.6846(10) . y
Pb1 O2 2.742(3) . y
Pb1 O4 2.841(3) 4_666 y
Pb1 C1 2.864(4) . y
C1 O2 1.237(5) . ?
C1 O1 1.278(5) . ?
C1 C2 1.519(6) . ?
C2 N1 1.355(5) . ?
C2 C3 1.379(6) . ?
C3 C4 1.390(7) . ?
C3 H3 0.95 . ?
C4 C5 1.387(7) . ?
C4 H4 0.95 . ?
C5 C6 1.392(6) . ?
C5 H5 0.95 . ?
C6 N1 1.324(6) . ?
C6 C7 1.519(6) . ?
C7 N2 1.485(5) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 N2 1.505(5) . ?
C8 C9 1.519(6) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 N3 1.477(5) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 N3 1.501(5) . ?
C10 C11 1.526(6) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 C12 1.519(6) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 N4 1.505(5) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 N4 1.495(5) . ?
C13 C14 1.517(6) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 N5 1.468(5) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C15 N5 1.498(5) . ?
C15 C16 1.529(6) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 C17 1.512(6) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 N2 1.518(5) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 N3 1.474(5) . ?
C18 C19 1.546(6) . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
C19 N5 1.483(5) . ?
C19 H19A 0.99 . ?
C19 H19B 0.99 . ?
C20 N4 1.481(5) . ?
C20 C21 1.527(6) . ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?
C21 O4 1.240(5) . ?
C21 O3 1.274(5) . ?
N2 H2 0.81(6) . ?
N4 H4A 0.78(6) . ?
O5 Cl2 1.418(4) . ?
O6 Cl2 1.442(3) . ?
O7 Cl2 1.403(4) . ?
O8 Cl2 1.430(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
O1 Pb1 O3 81.73(11) . 4_666 y
O1 Pb1 Cl1 85.74(8) . . y
O3 Pb1 Cl1 88.88(7) 4_666 . y
O1 Pb1 O2 51.28(10) . . y
O3 Pb1 O2 74.33(9) 4_666 . y
Cl1 Pb1 O2 135.10(7) . . y
O1 Pb1 O4 116.29(10) . 4_666 y
O3 Pb1 O4 49.33(9) 4_666 4_666 y
Cl1 Pb1 O4 123.74(7) . 4_666 y
O2 Pb1 O4 75.11(9) . 4_666 y
O1 Pb1 C1 25.90(11) . . y
O3 Pb1 C1 76.75(11) 4_666 . y
Cl1 Pb1 C1 110.86(9) . . y
O2 Pb1 C1 25.38(10) . . y
O4 Pb1 C1 95.75(10) 4_666 . y
O2 C1 O1 124.2(4) . . ?
O2 C1 C2 119.1(4) . . ?
O1 C1 C2 116.7(4) . . ?
O2 C1 Pb1 71.8(3) . . ?
O1 C1 Pb1 52.4(2) . . ?
C2 C1 Pb1 169.0(3) . . ?
N1 C2 C3 122.8(4) . . ?
N1 C2 C1 117.3(4) . . ?
C3 C2 C1 119.8(4) . . ?
C2 C3 C4 118.8(4) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 118.7(4) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 118.5(4) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
N1 C6 C5 123.4(4) . . ?
N1 C6 C7 118.4(4) . . ?
C5 C6 C7 118.2(4) . . ?
N2 C7 C6 113.5(3) . . ?
N2 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
N2 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
N2 C8 C9 114.2(3) . . ?
N2 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
N2 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N3 C9 C8 114.6(3) . . ?
N3 C9 H9A 108.6 . . ?
C8 C9 H9A 108.6 . . ?
N3 C9 H9B 108.6 . . ?
C8 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
N3 C10 C11 113.3(3) . . ?
N3 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
N3 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 C10 114.2(4) . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
N4 C12 C11 111.2(3) . . ?
N4 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
N4 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108 . . ?
N4 C13 C14 112.8(3) . . ?
N4 C13 H13A 109 . . ?
C14 C13 H13A 109 . . ?
N4 C13 H13B 109 . . ?
C14 C13 H13B 109 . . ?
H13A C13 H13B 107.8 . . ?
N5 C14 C13 114.8(3) . . ?
N5 C14 H14A 108.6 . . ?
C13 C14 H14A 108.6 . . ?
N5 C14 H14B 108.6 . . ?
C13 C14 H14B 108.6 . . ?
H14A C14 H14B 107.5 . . ?
N5 C15 C16 113.1(3) . . ?
N5 C15 H15A 109 . . ?
C16 C15 H15A 109 . . ?
N5 C15 H15B 109 . . ?
C16 C15 H15B 109 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C15 114.6(3) . . ?
C17 C16 H16A 108.6 . . ?
C15 C16 H16A 108.6 . . ?
C17 C16 H16B 108.6 . . ?
C15 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C16 C17 N2 112.8(3) . . ?
C16 C17 H17A 109 . . ?
N2 C17 H17A 109 . . ?
C16 C17 H17B 109 . . ?
N2 C17 H17B 109 . . ?
H17A C17 H17B 107.8 . . ?
N3 C18 C19 116.1(3) . . ?
N3 C18 H18A 108.3 . . ?
C19 C18 H18A 108.3 . . ?
N3 C18 H18B 108.3 . . ?
C19 C18 H18B 108.3 . . ?
H18A C18 H18B 107.4 . . ?
N5 C19 C18 115.9(3) . . ?
N5 C19 H19A 108.3 . . ?
C18 C19 H19A 108.3 . . ?
N5 C19 H19B 108.3 . . ?
C18 C19 H19B 108.3 . . ?
H19A C19 H19B 107.4 . . ?
N4 C20 C21 111.5(3) . . ?
N4 C20 H20A 109.3 . . ?
C21 C20 H20A 109.3 . . ?
N4 C20 H20B 109.3 . . ?
C21 C20 H20B 109.3 . . ?
H20A C20 H20B 108 . . ?
O4 C21 O3 124.7(4) . . ?
O4 C21 C20 117.7(4) . . ?
O3 C21 C20 117.6(4) . . ?
C6 N1 C2 117.7(4) . . ?
C7 N2 C8 110.7(3) . . ?
C7 N2 C17 110.2(3) . . ?
C8 N2 C17 110.5(3) . . ?
C7 N2 H2 109(4) . . ?
C8 N2 H2 109(4) . . ?
C17 N2 H2 106(4) . . ?
C18 N3 C9 114.1(3) . . ?
C18 N3 C10 109.8(3) . . ?
C9 N3 C10 107.6(3) . . ?
C20 N4 C13 113.1(3) . . ?
C20 N4 C12 111.5(3) . . ?
C13 N4 C12 111.5(3) . . ?
C20 N4 H4A 107(4) . . ?
C13 N4 H4A 105(4) . . ?
C12 N4 H4A 108(4) . . ?
C14 N5 C19 112.5(3) . . ?
C14 N5 C15 106.5(3) . . ?
C19 N5 C15 109.7(3) . . ?
C1 O1 Pb1 101.7(2) . . ?
C1 O2 Pb1 82.8(3) . . ?
C21 O3 Pb1 101.5(2) . 4_565 ?
O7 Cl2 O5 110.3(3) . . ?
O7 Cl2 O8 108.5(3) . . ?
O5 Cl2 O8 109.6(3) . . ?
O7 Cl2 O6 110.4(3) . . ?
O5 Cl2 O6 108.1(2) . . ?
O8 Cl2 O6 109.9(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
O2 C1 C2 N1 171.9(4) . . . . ?
O1 C1 C2 N1 -6.3(6) . . . . ?
Pb1 C1 C2 N1 0.2(17) . . . . ?
O2 C1 C2 C3 -7.3(6) . . . . ?
O1 C1 C2 C3 174.5(4) . . . . ?
Pb1 C1 C2 C3 -179.0(13) . . . . ?
N1 C2 C3 C4 1.0(7) . . . . ?
C1 C2 C3 C4 -179.8(4) . . . . ?
C2 C3 C4 C5 -2.8(8) . . . . ?
C3 C4 C5 C6 2.0(7) . . . . ?
C4 C5 C6 N1 0.6(7) . . . . ?
C4 C5 C6 C7 178.0(4) . . . . ?
N1 C6 C7 N2 -4.9(5) . . . . ?
C5 C6 C7 N2 177.6(4) . . . . ?
N2 C8 C9 N3 -62.6(5) . . . . ?
N3 C10 C11 C12 59.7(5) . . . . ?
C10 C11 C12 N4 -53.4(5) . . . . ?
N4 C13 C14 N5 -50.9(5) . . . . ?
N5 C15 C16 C17 64.9(5) . . . . ?
C15 C16 C17 N2 -53.5(5) . . . . ?
N3 C18 C19 N5 19.0(5) . . . . ?
N4 C20 C21 O4 164.9(4) . . . . ?
N4 C20 C21 O3 -15.0(5) . . . . ?
C5 C6 N1 C2 -2.3(6) . . . . ?
C7 C6 N1 C2 -179.7(4) . . . . ?
C3 C2 N1 C6 1.5(6) . . . . ?
C1 C2 N1 C6 -177.7(4) . . . . ?
C6 C7 N2 C8 164.1(3) . . . . ?
C6 C7 N2 C17 -73.3(4) . . . . ?
C9 C8 N2 C7 -74.9(4) . . . . ?
C9 C8 N2 C17 162.7(3) . . . . ?
C16 C17 N2 C7 165.4(3) . . . . ?
C16 C17 N2 C8 -72.0(4) . . . . ?
C19 C18 N3 C9 87.6(4) . . . . ?
C19 C18 N3 C10 -151.6(4) . . . . ?
C8 C9 N3 C18 -58.8(4) . . . . ?
C8 C9 N3 C10 179.2(3) . . . . ?
C11 C10 N3 C18 70.9(4) . . . . ?
C11 C10 N3 C9 -164.5(3) . . . . ?
C21 C20 N4 C13 163.0(3) . . . . ?
C21 C20 N4 C12 -70.5(4) . . . . ?
C14 C13 N4 C20 -68.7(4) . . . . ?
C14 C13 N4 C12 164.7(3) . . . . ?
C11 C12 N4 C20 155.4(4) . . . . ?
C11 C12 N4 C13 -77.2(4) . . . . ?
C13 C14 N5 C19 -65.5(5) . . . . ?
C13 C14 N5 C15 174.2(3) . . . . ?
C18 C19 N5 C14 89.8(4) . . . . ?
C18 C19 N5 C15 -151.8(4) . . . . ?
C16 C15 N5 C14 -172.1(3) . . . . ?
C16 C15 N5 C19 65.9(4) . . . . ?
O2 C1 O1 Pb1 0.3(5) . . . . ?
C2 C1 O1 Pb1 178.4(3) . . . . ?
O1 C1 O2 Pb1 -0.3(4) . . . . ?
C2 C1 O2 Pb1 -178.4(4) . . . . ?
O4 C21 O3 Pb1 -16.3(5) . . . 4_565 ?
C20 C21 O3 Pb1 163.6(3) . . . 4_565 ?

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
C7 H7A O3 0.99 2.52 3.125(5) 119.1 . yes
C7 H7A Cl1 0.99 2.59 3.452(4) 145.1 4_565 yes
C8 H8A O4 0.99 2.24 3.172(5) 156.9 4_566 yes
C12 H12A O2 0.99 2.59 3.575(5) 175.5 4_565 yes
C12 H12B Cl1 0.99 2.95 3.705(5) 134.3 3_666 yes
C13 H13A O5 0.99 2.43 3.352(6) 155.3 3_666 yes
C14 H14A O1 0.99 2.36 3.316(5) 163 . yes
C15 H15B O1 0.99 2.57 3.483(5) 152.8 . yes
C16 H16A O6 0.99 2.49 3.146(5) 123.6 4_566 yes
C16 H16B O4 0.99 2.43 3.401(5) 167.1 4_566 yes
C17 H17A O6 0.99 2.59 3.107(5) 112.4 4_566 yes
C17 H17A O8 0.99 2.61 3.559(7) 161.8 4_566 yes
C17 H17A Cl2 0.99 2.98 3.733(4) 133.9 4_566 yes
C17 H17B N1 0.99 2.53 3.079(5) 114.8 . yes
C18 H18B O5 0.99 2.55 3.354(6) 138.3 3_666 yes
C19 H19A O5 0.99 2.66 3.400(6) 131.7 3_666 yes
C19 H19A Cl2 0.99 2.87 3.777(4) 153.1 3_666 yes
C19 H19B O4 0.99 2.47 3.381(5) 152.1 4_566 yes
N2 H2 N5 0.81(6) 2.15(6) 2.793(5) 137(5) . yes
N4 H4A N3 0.78(6) 1.99(6) 2.681(5) 149(5) . yes
N4 H4A N5 0.78(6) 2.55(6) 2.952(5) 114(5) . yes

# SQUEEZE RESULTS (Version = 220119)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.500 115 38 ' '
2 0.500 0.500 0.000 115 38 ' '
# Missing Reflections Below sin(th)/lambda = 0.25
loop_
_platon_missing_refln_index_h
_platon_missing_refln_index_k
_platon_missing_refln_index_l
_platon_missing_refln_theta
0 1 1 1.941
4 2 1 7.810
-5 0 3 10.084
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
;
TITL shelxt_a.res in P2(1)/n
CELL   11.2878   19.5609   12.4512     90.00     93.31     90.00
SPGR P21/n
# Solvent Accessible Volume =       228
# Electrons Found in S.A.V. =        76
# Note: Atoms in Void are Labelled as Cxxx and Qxxx for all Others
C101 1.001 0.925 0.561 !       4.20 eA-3
C102 0.636 0.469 0.102 !       3.90 eA-3
C103 0.568 0.499 0.089 !       3.63 eA-3
C104 0.500 0.465 0.001 !       3.56 eA-3
C105 0.984 0.093 0.494 !       3.17 eA-3
Q106 0.858 0.312 0.629 !       1.78 eA-3
Q107 0.218 0.363 0.200 !       1.70 eA-3
Q108 0.141 0.607 0.366 !       1.59 eA-3
Q109 0.050 0.645 0.377 !       1.54 eA-3
Q110 0.186 0.080 0.248 !       1.35 eA-3
Q111 0.364 0.362 0.094 !       1.30 eA-3
Q112 0.798 0.359 0.593 !       0.96 eA-3
Q113 0.344 0.732 0.139 !       0.80 eA-3
Q114 0.426 0.424 0.898 !       0.79 eA-3
Q115 0.933 0.969 0.330 !       0.76 eA-3
C116 0.942 0.938 0.446 !       0.69 eA-3
Q117 0.223 0.651 0.075 !       0.66 eA-3
Q118 0.186 0.565 0.605 !       0.64 eA-3
Q119 0.029 0.138 0.578 !       0.64 eA-3
Q120 0.568 0.636 0.963 !       0.63 eA-3
Q121 0.688 0.450 0.375 !       0.63 eA-3
Q122 0.155 0.525 0.531 !       0.62 eA-3
Q123 0.073 0.050 0.457 !       0.60 eA-3
Q124 0.620 0.976 0.114 !       0.57 eA-3
Q125 0.187 0.420 0.957 !       0.57 eA-3
Q126 0.312 0.180 0.519 !       0.56 eA-3
C127 0.025 0.996 0.407 !       0.56 eA-3
Q128 0.519 0.011 0.159 !       0.55 eA-3
Q129 0.161 0.781 0.317 !       0.54 eA-3
Q130 0.685 0.126 0.803 !       0.54 eA-3
Q131 0.128 0.706 0.436 !       0.54 eA-3
Q132 0.342 0.200 0.555 !       0.54 eA-3
Q133 0.888 0.137 0.081 !       0.53 eA-3
Q134 0.076 0.316 0.986 !       0.53 eA-3
Q135 0.078 0.839 0.169 !       0.53 eA-3
Q136 0.683 0.658 0.383 !       0.52 eA-3
Q137 0.356 0.359 0.322 !       0.52 eA-3
Q138 0.672 0.684 0.033 !       0.51 eA-3
Q139 0.045 0.139 0.385 !       0.51 eA-3
Q140 0.583 0.558 0.201 !       0.51 eA-3
Q141 0.322 0.622 0.280 !       0.50 eA-3
Q142 0.217 0.079 0.562 !       0.50 eA-3
;





# END of CIF
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
_refine_special_details          SQUEEZE
####################################################################### 
# 
# 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_H2cb-teapa
_database_code_depnum_ccdc_archive 'CCDC 2032604'
loop_
_audit_author_name
_audit_author_address
'Andres De Blas'
;University of A Coruna
Spain
;
_audit_update_record             
;
2020-09-17 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;

_audit_creation_date             2016-07-21T13:34:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C21 H35 N5 O4, 0.743(Br), 1.257(Cl), 2(H2 O)'
_chemical_formula_sum            'C21 H39 Br0.74 Cl1.26 N5 O6'
_chemical_formula_weight         561.5

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   8.3269(2)
_cell_length_b                   18.7143(5)
_cell_length_c                   16.6875(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.729(3)
_cell_angle_gamma                90
_cell_volume                     2563.05(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    7811
_cell_measurement_theta_min      3.87
_cell_measurement_theta_max      28.21
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1181

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.38
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.724
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.644
_shelx_estimated_absorpt_T_max   0.898
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_measurement_device       'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_device_type  
'Oxford Diffraction Limited  Xcalibur, Sapphire2'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_number            17030
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.302
_diffrn_reflns_theta_max         29.275
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.864
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.864
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.864
_reflns_Friedel_coverage         0
_reflns_number_total             6047
_reflns_number_gt                5040
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0342P)²+0.4631P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6047
_refine_ls_number_parameters     327
_refine_ls_number_restraints     6
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0742
_refine_ls_wR_factor_gt          0.0689
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.057

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.4512(2) 0.56671(8) 0.41370(9) 0.0293(3) Uani 1 1 d . . . . .
C2 C 0.27707(18) 0.54279(8) 0.40404(9) 0.0280(3) Uani 1 1 d . . . . .
C3 C 0.1601(2) 0.58345(9) 0.43306(9) 0.0346(4) Uani 1 1 d . . . . .
H3 H 0.188 0.6277 0.4596 0.041 Uiso 1 1 calc R U . . .
C4 C 0.0022(2) 0.55816(10) 0.42248(10) 0.0394(4) Uani 1 1 d . . . . .
H4 H -0.081 0.5852 0.4409 0.047 Uiso 1 1 calc R U . . .
C5 C -0.03287(19) 0.49328(10) 0.38481(10) 0.0355(4) Uani 1 1 d . . . . .
H5 H -0.1404 0.4745 0.3774 0.043 Uiso 1 1 calc R U . . .
C6 C 0.09130(18) 0.45570(8) 0.35783(9) 0.0284(3) Uani 1 1 d . . . . .
C7 C 0.05213(18) 0.38529(8) 0.31562(10) 0.0318(3) Uani 1 1 d . . . . .
H7A H -0.0145 0.3565 0.3475 0.038 Uiso 1 1 calc R U . . .
H7B H -0.0143 0.3942 0.2615 0.038 Uiso 1 1 calc R U . . .
C8 C 0.29407(19) 0.31850(8) 0.38527(10) 0.0319(3) Uani 1 1 d . . . . .
H8A H 0.2382 0.2769 0.4048 0.038 Uiso 1 1 calc R U . . .
H8B H 0.2964 0.3573 0.4258 0.038 Uiso 1 1 calc R U . . .
C9 C 0.46739(19) 0.29775(8) 0.37851(10) 0.0333(4) Uani 1 1 d . . . . .
H9A H 0.4645 0.2541 0.3448 0.04 Uiso 1 1 calc R U . . .
H9B H 0.5268 0.286 0.4334 0.04 Uiso 1 1 calc R U . . .
C10 C 0.56111(18) 0.35536(8) 0.34181(9) 0.0286(3) Uani 1 1 d . . . . .
H10A H 0.5614 0.3995 0.3746 0.034 Uiso 1 1 calc R U . . .
H10B H 0.6756 0.3397 0.3451 0.034 Uiso 1 1 calc R U . . .
C11 C 0.57476(17) 0.43740(8) 0.23281(9) 0.0261(3) Uani 1 1 d . . . . .
H11A H 0.693 0.4276 0.2383 0.031 Uiso 1 1 calc R U . . .
H11B H 0.5604 0.4757 0.2719 0.031 Uiso 1 1 calc R U . . .
C12 C 0.51442(17) 0.46445(8) 0.14789(9) 0.0259(3) Uani 1 1 d . . . . .
H12A H 0.5741 0.5087 0.1389 0.031 Uiso 1 1 calc R U . . .
H12B H 0.5384 0.4283 0.1082 0.031 Uiso 1 1 calc R U . . .
C13 C 0.2680(2) 0.48461(8) 0.04303(9) 0.0317(3) Uani 1 1 d . . . . .
H13A H 0.3385 0.5165 0.0168 0.038 Uiso 1 1 calc R U . . .
H13B H 0.1577 0.506 0.0355 0.038 Uiso 1 1 calc R U . . .
C14 C 0.2588(2) 0.41211(9) 0.00187(9) 0.0334(3) Uani 1 1 d . . . . .
H14A H 0.2108 0.4181 -0.0562 0.04 Uiso 1 1 calc R U . . .
H14B H 0.3706 0.3933 0.0045 0.04 Uiso 1 1 calc R U . . .
C15 C 0.15873(19) 0.35798(9) 0.03959(10) 0.0346(4) Uani 1 1 d . . . . .
H15A H 0.0469 0.3768 0.0372 0.042 Uiso 1 1 calc R U . . .
H15B H 0.1512 0.3134 0.0072 0.042 Uiso 1 1 calc R U . . .
C16 C 0.10258(19) 0.30230(9) 0.16089(10) 0.0357(4) Uani 1 1 d . . . . .
H16A H 0.0723 0.2587 0.1283 0.043 Uiso 1 1 calc R U . . .
H16B H 0.0044 0.3328 0.1561 0.043 Uiso 1 1 calc R U . . .
C17 C 0.1525(2) 0.28089(8) 0.24890(10) 0.0352(4) Uani 1 1 d . . . . .
H17A H 0.0611 0.255 0.2668 0.042 Uiso 1 1 calc R U . . .
H17B H 0.246 0.2476 0.2534 0.042 Uiso 1 1 calc R U . . .
C18 C 0.37963(19) 0.29822(8) 0.12889(10) 0.0317(3) Uani 1 1 d . . . . .
H18A H 0.4246 0.3079 0.0787 0.038 Uiso 1 1 calc R U . . .
H18B H 0.3496 0.247 0.1281 0.038 Uiso 1 1 calc R U . . .
C19 C 0.51580(18) 0.31096(8) 0.20223(9) 0.0295(3) Uani 1 1 d . . . . .
H19A H 0.5277 0.2671 0.2359 0.035 Uiso 1 1 calc R U . . .
H19B H 0.6194 0.318 0.1816 0.035 Uiso 1 1 calc R U . . .
C20 C 0.29608(18) 0.54585(7) 0.17551(9) 0.0280(3) Uani 1 1 d . . . . .
H20A H 0.3207 0.5883 0.1443 0.034 Uiso 1 1 calc R U . . .
H20B H 0.3651 0.548 0.2299 0.034 Uiso 1 1 calc R U . . .
C21 C 0.11853(19) 0.54708(8) 0.18460(9) 0.0275(3) Uani 1 1 d . . . . .
N1 N 0.24392(15) 0.47985(7) 0.36590(7) 0.0274(3) Uani 1 1 d . . . . .
N2 N 0.19917(15) 0.34328(6) 0.30490(8) 0.0267(3) Uani 1 1 d . . . . .
H2A H 0.2673(13) 0.3733(6) 0.2805(5) 0.032 Uiso 1 1 calc R U . . .
N3 N 0.49296(14) 0.37225(6) 0.25538(7) 0.0231(3) Uani 1 1 d . . . . .
N4 N 0.33469(14) 0.47980(6) 0.13288(7) 0.0235(3) Uani 1 1 d . . . . .
H4A H 0.2824(10) 0.4414(7) 0.1541(4) 0.028 Uiso 1 1 calc R U . . .
N5 N 0.22852(14) 0.34095(7) 0.12576(8) 0.0273(3) Uani 1 1 d . . . . .
O1 O 0.56287(14) 0.52788(6) 0.40565(8) 0.0422(3) Uani 1 1 d . . . . .
O2 O 0.46843(16) 0.63525(6) 0.43213(8) 0.0438(3) Uani 1 1 d . . . . .
H2B H 0.574(3) 0.6493(5) 0.4297(14) 0.066 Uiso 1 1 calc R U . . .
O3 O 0.02793(13) 0.49708(6) 0.16782(7) 0.0360(3) Uani 1 1 d . . . . .
O4 O 0.08035(15) 0.60932(6) 0.21324(7) 0.0375(3) Uani 1 1 d . . . . .
H4B H -0.025(3) 0.6089(4) 0.2194(12) 0.056 Uiso 1 1 calc R U . . .
Cl1 Cl -0.27824(3) 0.64084(2) 0.22732(2) 0.03646(9) Uani 0.521(2) 1 d . . P A 1
Cl2 Cl 0.79583(3) 0.83782(2) 0.49024(2) 0.0274(1) Uani 0.741(2) 1 d . . P B 1
Br1 Br -0.27824(3) 0.64084(2) 0.22732(2) 0.03646(9) Uani 0.479(2) 1 d . . P A 2
Br2 Br 0.79583(3) 0.83782(2) 0.49024(2) 0.0274(1) Uani 0.259(2) 1 d . . P B 2
O5 O 0.74481(15) 0.68628(6) 0.41470(8) 0.0407(3) Uani 1 1 d D . . . .
H51W H 0.763(3) 0.7334(9) 0.4306(12) 0.061 Uiso 1 1 d D U . . .
H52W H 0.752(3) 0.6818(11) 0.3619(10) 0.061 Uiso 1 1 d D U . . .
O6 O 1.10504(16) 0.74382(7) 0.58150(10) 0.0543(4) Uani 1 1 d D . . . .
H61W H 1.017(2) 0.7669(12) 0.5539(13) 0.082 Uiso 1 1 d D U . . .
H62W H 1.146(3) 0.7726(12) 0.6246(12) 0.082 Uiso 1 1 d D U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 O1 1.2057(18) . ?
C1 O2 1.3212(18) . ?
C1 C2 1.500(2) . ?
C2 N1 1.3450(19) . ?
C2 C3 1.386(2) . ?
C3 C4 1.380(2) . ?
C3 H3 0.95 . ?
C4 C5 1.376(3) . ?
C4 H4 0.95 . ?
C5 C6 1.387(2) . ?
C5 H5 0.95 . ?
C6 N1 1.3340(19) . ?
C6 C7 1.504(2) . ?
C7 N2 1.4911(19) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 N2 1.5100(19) . ?
C8 C9 1.517(2) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C10 1.519(2) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 N3 1.4918(18) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 N3 1.4761(18) . ?
C11 C12 1.509(2) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 N4 1.5028(18) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 N4 1.5110(18) . ?
C13 C14 1.517(2) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 C15 1.514(2) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C15 N5 1.492(2) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 N5 1.4746(19) . ?
C16 C17 1.511(2) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 N2 1.5049(19) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 N5 1.4843(19) . ?
C18 C19 1.540(2) . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
C19 N3 1.4818(18) . ?
C19 H19A 0.99 . ?
C19 H19B 0.99 . ?
C20 N4 1.4882(18) . ?
C20 C21 1.512(2) . ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?
C21 O3 1.2050(18) . ?
C21 O4 1.3180(17) . ?
N2 H2A 0.939(17) . ?
N4 H4A 0.940(17) . ?
O2 H2B 0.92(2) . ?
O4 H4B 0.90(2) . ?
O5 H51W 0.926(15) . ?
O5 H52W 0.897(15) . ?
O6 H61W 0.904(16) . ?
O6 H62W 0.918(16) . ?

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 C1 O2 123.74(15) . . ?
O1 C1 C2 123.91(14) . . ?
O2 C1 C2 112.34(13) . . ?
N1 C2 C3 123.08(15) . . ?
N1 C2 C1 115.45(13) . . ?
C3 C2 C1 121.47(14) . . ?
C4 C3 C2 118.52(15) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C5 C4 C3 119.01(15) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 118.92(15) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
N1 C6 C5 123.04(15) . . ?
N1 C6 C7 118.14(13) . . ?
C5 C6 C7 118.80(14) . . ?
N2 C7 C6 113.63(12) . . ?
N2 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
N2 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
N2 C8 C9 111.98(12) . . ?
N2 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N2 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C10 114.10(12) . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
C10 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
N3 C10 C9 113.75(12) . . ?
N3 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
N3 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
N3 C11 C12 114.97(11) . . ?
N3 C11 H11A 108.5 . . ?
C12 C11 H11A 108.5 . . ?
N3 C11 H11B 108.5 . . ?
C12 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
N4 C12 C11 112.64(11) . . ?
N4 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
N4 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
N4 C13 C14 112.21(12) . . ?
N4 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
N4 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 113.54(13) . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
N5 C15 C14 113.05(12) . . ?
N5 C15 H15A 109 . . ?
C14 C15 H15A 109 . . ?
N5 C15 H15B 109 . . ?
C14 C15 H15B 109 . . ?
H15A C15 H15B 107.8 . . ?
N5 C16 C17 114.78(12) . . ?
N5 C16 H16A 108.6 . . ?
C17 C16 H16A 108.6 . . ?
N5 C16 H16B 108.6 . . ?
C17 C16 H16B 108.6 . . ?
H16A C16 H16B 107.5 . . ?
N2 C17 C16 113.42(13) . . ?
N2 C17 H17A 108.9 . . ?
C16 C17 H17A 108.9 . . ?
N2 C17 H17B 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
N5 C18 C19 116.78(12) . . ?
N5 C18 H18A 108.1 . . ?
C19 C18 H18A 108.1 . . ?
N5 C18 H18B 108.1 . . ?
C19 C18 H18B 108.1 . . ?
H18A C18 H18B 107.3 . . ?
N3 C19 C18 116.35(12) . . ?
N3 C19 H19A 108.2 . . ?
C18 C19 H19A 108.2 . . ?
N3 C19 H19B 108.2 . . ?
C18 C19 H19B 108.2 . . ?
H19A C19 H19B 107.4 . . ?
N4 C20 C21 110.77(12) . . ?
N4 C20 H20A 109.5 . . ?
C21 C20 H20A 109.5 . . ?
N4 C20 H20B 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
O3 C21 O4 126.20(14) . . ?
O3 C21 C20 123.32(13) . . ?
O4 C21 C20 110.48(13) . . ?
C6 N1 C2 117.40(13) . . ?
C7 N2 C17 110.64(12) . . ?
C7 N2 C8 111.86(12) . . ?
C17 N2 C8 110.78(12) . . ?
C7 N2 H2A 107.8 . . ?
C17 N2 H2A 107.8 . . ?
C8 N2 H2A 107.8 . . ?
C11 N3 C19 112.03(11) . . ?
C11 N3 C10 107.77(11) . . ?
C19 N3 C10 110.39(11) . . ?
C20 N4 C12 111.62(11) . . ?
C20 N4 C13 110.60(11) . . ?
C12 N4 C13 111.45(11) . . ?
C20 N4 H4A 107.7 . . ?
C12 N4 H4A 107.7 . . ?
C13 N4 H4A 107.7 . . ?
C16 N5 C18 112.16(12) . . ?
C16 N5 C15 107.49(12) . . ?
C18 N5 C15 109.81(12) . . ?
C1 O2 H2B 109.5 . . ?
C21 O4 H4B 109.5 . . ?
H51W O5 H52W 109.7(18) . . ?
H61W O6 H62W 106(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
O1 C1 C2 N1 -16.1(2) . . . . ?
O2 C1 C2 N1 163.92(13) . . . . ?
O1 C1 C2 C3 163.71(16) . . . . ?
O2 C1 C2 C3 -16.2(2) . . . . ?
N1 C2 C3 C4 0.1(2) . . . . ?
C1 C2 C3 C4 -179.70(14) . . . . ?
C2 C3 C4 C5 1.0(2) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C4 C5 C6 N1 -0.7(2) . . . . ?
C4 C5 C6 C7 -179.15(14) . . . . ?
N1 C6 C7 N2 13.41(19) . . . . ?
C5 C6 C7 N2 -168.08(13) . . . . ?
N2 C8 C9 C10 53.68(18) . . . . ?
C8 C9 C10 N3 -64.62(17) . . . . ?
N3 C11 C12 N4 57.33(16) . . . . ?
N4 C13 C14 C15 56.58(18) . . . . ?
C13 C14 C15 N5 -62.95(18) . . . . ?
N5 C16 C17 N2 59.18(18) . . . . ?
N5 C18 C19 N3 -9.2(2) . . . . ?
N4 C20 C21 O3 8.0(2) . . . . ?
N4 C20 C21 O4 -172.30(12) . . . . ?
C5 C6 N1 C2 1.8(2) . . . . ?
C7 C6 N1 C2 -179.78(13) . . . . ?
C3 C2 N1 C6 -1.5(2) . . . . ?
C1 C2 N1 C6 178.35(12) . . . . ?
C6 C7 N2 C17 -169.23(13) . . . . ?
C6 C7 N2 C8 66.74(16) . . . . ?
C16 C17 N2 C7 72.39(16) . . . . ?
C16 C17 N2 C8 -162.96(13) . . . . ?
C9 C8 N2 C7 -161.32(13) . . . . ?
C9 C8 N2 C17 74.73(16) . . . . ?
C12 C11 N3 C19 61.21(15) . . . . ?
C12 C11 N3 C10 -177.17(12) . . . . ?
C18 C19 N3 C11 -94.71(15) . . . . ?
C18 C19 N3 C10 145.18(13) . . . . ?
C9 C10 N3 C11 169.37(12) . . . . ?
C9 C10 N3 C19 -67.98(15) . . . . ?
C21 C20 N4 C12 -160.40(12) . . . . ?
C21 C20 N4 C13 74.90(15) . . . . ?
C11 C12 N4 C20 73.23(15) . . . . ?
C11 C12 N4 C13 -162.55(12) . . . . ?
C14 C13 N4 C20 -162.83(13) . . . . ?
C14 C13 N4 C12 72.38(16) . . . . ?
C17 C16 N5 C18 59.45(17) . . . . ?
C17 C16 N5 C15 -179.75(13) . . . . ?
C19 C18 N5 C16 -94.70(15) . . . . ?
C19 C18 N5 C15 145.85(14) . . . . ?
C14 C15 N5 C16 166.61(13) . . . . ?
C14 C15 N5 C18 -71.13(16) . . . . ?

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
C7 H7A O6 0.99 2.41 3.355(2) 159.9 3_666
C7 H7B O3 0.99 2.54 3.214(2) 125.1 .
C8 H8A Cl2 0.99 2.82 3.7363(15) 155.1 3_666
C8 H8B N1 0.99 2.51 3.058(2) 114.5 .
C10 H10A O1 0.99 2.46 3.3992(19) 158.6 .
C10 H10B O6 0.99 2.55 3.4071(19) 144.3 3_766
C11 H11B O1 0.99 2.43 3.3604(19) 155.8 .
C12 H12A Br1 0.99 3.03 3.8549(15) 141.4 1_655
C12 H12B Cl2 0.99 2.87 3.8285(15) 163.1 2_645
C13 H13A Cl2 0.99 2.77 3.4557(16) 126.5 4_575
C13 H13B O3 0.99 2.62 3.129(2) 111.9 .
C14 H14B Cl2 0.99 2.95 3.9422(17) 179.2 2_645
C15 H15A Cl2 0.99 2.91 3.7523(16) 144 2_545
C16 H16A O2 0.99 2.52 3.496(2) 168.6 2_545
C18 H18A Cl2 0.99 2.82 3.6906(17) 146.9 2_645
C19 H19B Br2 0.99 3.09 3.8381(16) 133.4 2_645
C20 H20A Cl2 0.99 2.9 3.7811(16) 149.4 4_575
N2 H2A N3 0.94 1.99 2.7649(17) 138.2 .
N4 H4A N5 0.94 1.97 2.7407(17) 137.7 .
O2 H2B O5 0.92 1.64 2.5533(18) 169.4 .
O4 H4B Cl1 0.9 2.22 3.0913(12) 163.6 .
O5 H51W Cl2 0.926(15) 2.189(15) 3.1034(12) 169.3(18) .
O5 H52W Cl1 0.897(15) 2.346(16) 3.2147(13) 163.2(19) 1_655
O6 H61W Cl2 0.904(16) 2.374(17) 3.2738(13) 174(2) .
O6 H62W Cl1 0.918(16) 2.364(17) 3.2750(17) 171(2) 4_776



# END of CIF
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
