# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_lcs18005(comp2)
_database_code_depnum_ccdc_archive 'CCDC 1900402'
loop_
_audit_author_name
_audit_author_address
'Luis Cunha Silva'
;REQUIMTE LAQV and University of Porto
Portugal
;
_audit_update_record             
;
2019-02-28 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;

# ========================================================================= #

_audit_creation_method           'SHELXL-2014/7 and enCIFer'
_shelx_SHELXL_version_number     2014/7
_audit_creation_date             '15 November 2018'

# ========================================================================= #


_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C36 H36 N24 O12, 2(Cl2 H4 Mo O4), 2(H Cl), 17(H2 O)'
_chemical_formula_sum            'C36 H80 Cl6 Mo2 N24 O37'
_chemical_formula_weight         1845.82

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mo Mo -1.6832 0.6857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.5039(11)
_cell_length_b                   11.9145(10)
_cell_length_c                   14.6279(13)
_cell_angle_alpha                74.687(4)
_cell_angle_beta                 68.753(4)
_cell_angle_gamma                87.232(4)
_cell_volume                     1799.8(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9888
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      29.22

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_F_000             946
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.678
_shelx_estimated_absorpt_T_min   0.822
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_process_details   
; 
'SADABS V2012/1 (Bruker AXS Inc.)' 
;


_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker X8 Kappa CCD APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            60089
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.780
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             8909


_reflns_number_gt                8001
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2012)'
_computing_cell_refinement       'SAINT (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2014)'


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0373P)²+1.3780P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8909
_refine_ls_number_parameters     547
_refine_ls_number_restraints     39
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0755
_refine_ls_wR_factor_gt          0.0732
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mo01 Mo 0.19718(2) 1.14501(2) 0.18887(2) 0.01648(5) Uani 1 1 d . . . . .
Cl1 Cl 0.34665(5) 1.30077(4) 0.08241(3) 0.02767(11) Uani 1 1 d . . . . .
Cl2 Cl 0.06241(5) 0.97914(4) 0.23451(4) 0.03089(12) Uani 1 1 d . . . . .
O1 O 0.08618(15) 1.23001(14) 0.24104(12) 0.0375(4) Uani 1 1 d . . . . .
O2 O 0.26369(14) 1.09668(12) 0.27658(11) 0.0294(3) Uani 1 1 d . . . . .
O1W O 0.15400(13) 1.17176(13) 0.04851(10) 0.0268(3) Uani 1 1 d D . . . .
H1W H 0.192(2) 1.2226(18) -0.0068(12) 0.040 Uiso 1 1 d D U . . .
H2W H 0.0835(13) 1.150(2) 0.0513(18) 0.040 Uiso 1 1 d D U . . .
O2W O 0.33941(13) 1.03692(13) 0.09964(11) 0.0276(3) Uani 1 1 d D . . . .
H3W H 0.339(2) 1.029(2) 0.0439(12) 0.041 Uiso 1 1 d D U . . .
H4W H 0.4139(12) 1.041(2) 0.0967(19) 0.041 Uiso 1 1 d D U . . .
Cl3 Cl 0.74112(4) 1.26327(4) -0.02042(3) 0.02049(9) Uani 1 1 d . . . . .
O3 O 0.53310(11) 0.86673(10) 0.52268(9) 0.0189(3) Uani 1 1 d . . . . .
O4 O 0.53965(11) 0.87818(11) 0.27408(9) 0.0192(3) Uani 1 1 d . . . . .
O5 O 0.72726(11) 0.67758(10) 0.14569(9) 0.0184(2) Uani 1 1 d . . . . .
O6 O 0.10122(13) 0.50405(11) 0.73230(10) 0.0237(3) Uani 1 1 d . . . . .
O7 O 0.13560(13) 0.48939(11) 0.48448(10) 0.0260(3) Uani 1 1 d . . . . .
O8 O 0.29105(12) 0.30638(10) 0.36184(10) 0.0208(3) Uani 1 1 d . . . . .
N1 N 0.38419(13) 0.78522(12) 0.68050(10) 0.0155(3) Uani 1 1 d . . . . .
N2 N 0.32516(13) 0.83975(12) 0.54747(10) 0.0152(3) Uani 1 1 d . . . . .
N3 N 0.33222(13) 0.84234(12) 0.37918(11) 0.0152(3) Uani 1 1 d . . . . .
N4 N 0.40011(13) 0.77226(12) 0.24426(11) 0.0158(3) Uani 1 1 d . . . . .
N5 N 0.52529(13) 0.62910(11) 0.16667(11) 0.0146(3) Uani 1 1 d . . . . .
N6 N 0.66493(13) 0.49324(12) 0.15149(11) 0.0158(3) Uani 1 1 d . . . . .
N7 N 0.21182(14) 0.63586(12) 0.76542(11) 0.0168(3) Uani 1 1 d . . . . .
N8 N 0.15308(13) 0.69299(12) 0.63266(11) 0.0159(3) Uani 1 1 d . . . . .
N9 N 0.17114(14) 0.68512(12) 0.46524(11) 0.0164(3) Uani 1 1 d . . . . .
N10 N 0.23461(13) 0.61724(12) 0.32845(11) 0.0160(3) Uani 1 1 d . . . . .
N11 N 0.35285(13) 0.48096(12) 0.23896(11) 0.0149(3) Uani 1 1 d . . . . .
N12 N 0.49113(13) 0.34582(11) 0.24160(10) 0.0148(3) Uani 1 1 d . . . . .
C1 C 0.46591(16) 0.77120(13) 0.73703(13) 0.0154(3) Uani 1 1 d . . . . .
H1A H 0.4214 0.7911 0.8021 0.018 Uiso 1 1 calc R U . . .
H1B H 0.5393 0.8266 0.6980 0.018 Uiso 1 1 calc R U . . .
C2 C 0.42532(16) 0.83331(13) 0.57747(12) 0.0145(3) Uani 1 1 d . . . . .
C3 C 0.33102(17) 0.90985(14) 0.44847(12) 0.0160(3) Uani 1 1 d . . . . .
H3A H 0.2582 0.9593 0.4574 0.019 Uiso 1 1 calc R U . . .
H3B H 0.4073 0.9622 0.4176 0.019 Uiso 1 1 calc R U . . .
C4 C 0.43448(16) 0.83422(13) 0.29741(12) 0.0151(3) Uani 1 1 d . . . . .
C5 C 0.48378(16) 0.74744(13) 0.15180(12) 0.0151(3) Uani 1 1 d . . . . .
H5A H 0.5578 0.8025 0.1221 0.018 Uiso 1 1 calc R U . . .
H5B H 0.4411 0.7608 0.1023 0.018 Uiso 1 1 calc R U . . .
C6 C 0.64652(16) 0.60643(14) 0.15480(12) 0.0146(3) Uani 1 1 d . . . . .
C7 C 0.78273(16) 0.43896(14) 0.14050(12) 0.0162(3) Uani 1 1 d . . . . .
H7A H 0.8504 0.5007 0.1124 0.019 Uiso 1 1 calc R U . . .
H7B H 0.7985 0.3923 0.0907 0.019 Uiso 1 1 calc R U . . .
C8 C 0.15117(16) 0.60041(14) 0.71214(13) 0.0159(3) Uani 1 1 d . . . . .
C9 C 0.20895(16) 0.79881(14) 0.63289(12) 0.0154(3) Uani 1 1 d . . . . .
H9 H 0.1480 0.8616 0.6404 0.018 Uiso 1 1 calc R U . . .
C10 C 0.55670(15) 0.43681(13) 0.15030(12) 0.0137(3) Uani 1 1 d . . . . .
H10 H 0.5771 0.4092 0.0876 0.016 Uiso 1 1 calc R U . . .
C11 C 0.46219(15) 0.53442(13) 0.15343(12) 0.0135(3) Uani 1 1 d . . . . .
H11 H 0.4445 0.5585 0.0891 0.016 Uiso 1 1 calc R U . . .
C12 C 0.26692(15) 0.74096(13) 0.28645(12) 0.0141(3) Uani 1 1 d . . . . .
H12 H 0.2253 0.7774 0.2373 0.017 Uiso 1 1 calc R U . . .
C13 C 0.22011(15) 0.78890(14) 0.38207(12) 0.0145(3) Uani 1 1 d . . . . .
H13 H 0.1545 0.8465 0.3793 0.017 Uiso 1 1 calc R U . . .
C14 C 0.25072(16) 0.75945(14) 0.72599(12) 0.0148(3) Uani 1 1 d . . . . .
H14 H 0.2095 0.8035 0.7778 0.018 Uiso 1 1 calc R U . . .
C15 C 0.08836(16) 0.68829(16) 0.56590(13) 0.0180(3) Uani 1 1 d . . . . .
H15A H 0.0374 0.7574 0.5602 0.022 Uiso 1 1 calc R U . . .
H15B H 0.0307 0.6181 0.5963 0.022 Uiso 1 1 calc R U . . .
C16 C 0.17659(15) 0.58722(14) 0.43185(13) 0.0164(3) Uani 1 1 d . . . . .
C17 C 0.23640(16) 0.53667(14) 0.26927(13) 0.0164(3) Uani 1 1 d . . . . .
H17A H 0.1682 0.4760 0.3099 0.020 Uiso 1 1 calc R U . . .
H17B H 0.2199 0.5793 0.2076 0.020 Uiso 1 1 calc R U . . .
C18 C 0.37075(16) 0.37106(14) 0.28898(12) 0.0146(3) Uani 1 1 d . . . . .
O3W O -0.07246(16) 1.11151(15) 0.06925(15) 0.0457(5) Uani 1 1 d D . . . .
H5W H -0.114(3) 1.151(2) 0.035(2) 0.069 Uiso 1 1 d D U . . .
H6W H -0.087(3) 1.0389(9) 0.083(3) 0.069 Uiso 1 1 d D U . . .
O4W O 0.58539(13) 1.03027(11) 0.08123(10) 0.0227(3) Uani 1 1 d D . . . .
H7W H 0.624(2) 1.0961(12) 0.0585(17) 0.034 Uiso 1 1 d D U . . .
H8W H 0.589(2) 0.9930(17) 0.1378(11) 0.034 Uiso 1 1 d D U . . .
O5W O 0.03926(14) 0.29028(13) 0.61863(12) 0.0359(4) Uani 1 1 d D . . . .
H9W H 0.072(3) 0.3569(14) 0.5826(17) 0.054 Uiso 1 1 d D U . . .
H10W H 0.023(3) 0.284(2) 0.6808(8) 0.054 Uiso 1 1 d D U . . .
O6W O 0.00933(14) 0.28117(12) 0.81342(13) 0.0358(4) Uani 1 1 d D . . . .
H11W H 0.044(2) 0.3481(14) 0.799(2) 0.054 Uiso 1 1 d D U . . .
H12W H -0.0615(15) 0.273(2) 0.8611(17) 0.054 Uiso 1 1 d D U . . .
O7W O 0.18230(13) 0.11776(12) 0.82275(11) 0.0271(3) Uani 1 1 d D . . . .
H13W H 0.2458(15) 0.1548(19) 0.819(2) 0.041 Uiso 1 1 d D U . . .
H14W H 0.1182(15) 0.1590(19) 0.834(2) 0.041 Uiso 1 1 d D U . . .
O8W O 0.27288(13) 0.04606(13) 0.65251(12) 0.0306(3) Uani 1 1 d D . . . .
H15W H 0.3484(11) 0.068(2) 0.6207(17) 0.046 Uiso 1 1 d D U . . .
H16W H 0.241(2) 0.065(2) 0.7077(12) 0.046 Uiso 1 1 d D U . . .
O9W O 0.17454(17) 0.15144(14) 0.53287(11) 0.0392(4) Uani 1 1 d D . . . .
H17W H 0.228(2) 0.185(2) 0.4776(13) 0.059 Uiso 1 1 d D U . . .
H18W H 0.125(2) 0.196(2) 0.562(2) 0.059 Uiso 1 1 d D U . . .
O10W O 0.0000 0.0000 0.5000 0.087(2) Uani 0.5 2 d S . P A 2
O13W O 0.5994(9) 0.6032(6) 0.4395(6) 0.134(3) Uani 0.5 1 d . . P B 1
O12W O 0.5253(10) 0.5054(10) 0.4570(6) 0.149(3) Uani 0.5 1 d . U P C 2
O11W O 0.5418(11) 0.4516(10) 0.3986(7) 0.089(3) Uani 0.25 1 d . U P D 1


_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
Mo01 O1 1.6779(15) . ?
Mo01 O2 1.6859(14) . ?
Mo01 O1W 2.2231(14) . ?
Mo01 O2W 2.2750(14) . ?
Mo01 Cl2 2.3672(5) . ?
Mo01 Cl1 2.3804(5) . ?
O1W H1W 0.851(9) . ?
O1W H2W 0.848(9) . ?
O2W H3W 0.848(9) . ?
O2W H4W 0.846(9) . ?
O3 C2 1.224(2) . ?
O4 C4 1.234(2) . ?
O5 C6 1.235(2) . ?
O6 C8 1.224(2) . ?
O7 C16 1.221(2) . ?
O8 C18 1.223(2) . ?
N1 C2 1.370(2) . ?
N1 C1 1.439(2) . ?
N1 C14 1.446(2) . ?
N2 C2 1.366(2) . ?
N2 C3 1.448(2) . ?
N2 C9 1.455(2) . ?
N3 C4 1.362(2) . ?
N3 C3 1.447(2) . ?
N3 C13 1.448(2) . ?
N4 C4 1.364(2) . ?
N4 C5 1.443(2) . ?
N4 C12 1.455(2) . ?
N5 C6 1.364(2) . ?
N5 C5 1.453(2) . ?
N5 C11 1.461(2) . ?
N6 C6 1.366(2) . ?
N6 C7 1.447(2) . ?
N6 C10 1.451(2) . ?
N7 C8 1.367(2) . ?
N7 C7 1.450(2) 2_666 ?
N7 C14 1.459(2) . ?
N8 C8 1.369(2) . ?
N8 C15 1.439(2) . ?
N8 C9 1.444(2) . ?
N9 C16 1.369(2) . ?
N9 C15 1.444(2) . ?
N9 C13 1.450(2) . ?
N10 C16 1.366(2) . ?
N10 C17 1.448(2) . ?
N10 C12 1.4483(19) . ?
N11 C18 1.367(2) . ?
N11 C11 1.438(2) . ?
N11 C17 1.439(2) . ?
N12 C18 1.365(2) . ?
N12 C1 1.449(2) 2_666 ?
N12 C10 1.4533(19) . ?
C1 N12 1.450(2) 2_666 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 N7 1.450(2) 2_666 ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 C14 1.556(2) . ?
C9 H9 1.0000 . ?
C10 C11 1.551(2) . ?
C10 H10 1.0000 . ?
C11 H11 1.0000 . ?
C12 C13 1.555(2) . ?
C12 H12 1.0000 . ?
C13 H13 1.0000 . ?
C14 H14 1.0000 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
O3W H5W 0.855(10) . ?
O3W H6W 0.846(10) . ?
O4W H7W 0.843(9) . ?
O4W H8W 0.845(9) . ?
O5W H9W 0.845(10) . ?
O5W H10W 0.842(10) . ?
O6W H11W 0.852(10) . ?
O6W H12W 0.848(10) . ?
O7W H13W 0.850(9) . ?
O7W H14W 0.856(9) . ?
O8W H15W 0.840(10) . ?
O8W H16W 0.843(9) . ?
O9W H17W 0.826(10) . ?
O9W H18W 0.831(10) . ?
O12W O12W 1.153(16) 2_666 ?

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 Mo01 O2 103.55(8) . . ?
O1 Mo01 O1W 95.01(7) . . ?
O2 Mo01 O1W 161.42(7) . . ?
O1 Mo01 O2W 172.23(7) . . ?
O2 Mo01 O2W 84.21(6) . . ?
O1W Mo01 O2W 77.22(6) . . ?
O1 Mo01 Cl2 96.12(6) . . ?
O2 Mo01 Cl2 97.61(5) . . ?
O1W Mo01 Cl2 79.56(4) . . ?
O2W Mo01 Cl2 82.95(4) . . ?
O1 Mo01 Cl1 95.48(6) . . ?
O2 Mo01 Cl1 97.11(5) . . ?
O1W Mo01 Cl1 81.52(4) . . ?
O2W Mo01 Cl1 83.12(4) . . ?
Cl2 Mo01 Cl1 158.563(19) . . ?
Mo01 O1W H1W 123.8(16) . . ?
Mo01 O1W H2W 121.0(16) . . ?
H1W O1W H2W 112.0(19) . . ?
Mo01 O2W H3W 121.4(17) . . ?
Mo01 O2W H4W 118.1(17) . . ?
H3W O2W H4W 109.6(19) . . ?
C2 N1 C1 122.36(14) . . ?
C2 N1 C14 113.16(14) . . ?
C1 N1 C14 124.31(14) . . ?
C2 N2 C3 121.85(14) . . ?
C2 N2 C9 112.16(13) . . ?
C3 N2 C9 123.69(14) . . ?
C4 N3 C3 124.03(14) . . ?
C4 N3 C13 112.65(14) . . ?
C3 N3 C13 122.85(14) . . ?
C4 N4 C5 124.24(14) . . ?
C4 N4 C12 112.61(14) . . ?
C5 N4 C12 122.99(14) . . ?
C6 N5 C5 121.53(13) . . ?
C6 N5 C11 111.40(13) . . ?
C5 N5 C11 122.55(14) . . ?
C6 N6 C7 123.88(14) . . ?
C6 N6 C10 112.34(14) . . ?
C7 N6 C10 123.52(14) . . ?
C8 N7 C7 121.88(14) . 2_666 ?
C8 N7 C14 112.47(13) . . ?
C7 N7 C14 124.96(14) 2_666 . ?
C8 N8 C15 122.40(14) . . ?
C8 N8 C9 113.23(14) . . ?
C15 N8 C9 123.70(14) . . ?
C16 N9 C15 121.24(14) . . ?
C16 N9 C13 112.28(14) . . ?
C15 N9 C13 123.24(14) . . ?
C16 N10 C17 121.39(14) . . ?
C16 N10 C12 112.57(14) . . ?
C17 N10 C12 124.70(14) . . ?
C18 N11 C11 112.98(13) . . ?
C18 N11 C17 123.17(14) . . ?
C11 N11 C17 123.86(13) . . ?
C18 N12 C1 122.05(13) . 2_666 ?
C18 N12 C10 112.33(13) . . ?
C1 N12 C10 123.20(14) 2_666 . ?
N1 C1 N12 113.30(13) . 2_666 ?
N1 C1 H1A 108.9 . . ?
N12 C1 H1A 108.9 2_666 . ?
N1 C1 H1B 108.9 . . ?
N12 C1 H1B 108.9 2_666 . ?
H1A C1 H1B 107.7 . . ?
O3 C2 N2 126.28(15) . . ?
O3 C2 N1 125.43(16) . . ?
N2 C2 N1 108.28(14) . . ?
N3 C3 N2 113.85(13) . . ?
N3 C3 H3A 108.8 . . ?
N2 C3 H3A 108.8 . . ?
N3 C3 H3B 108.8 . . ?
N2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
O4 C4 N3 125.61(16) . . ?
O4 C4 N4 125.87(16) . . ?
N3 C4 N4 108.50(14) . . ?
N4 C5 N5 113.56(13) . . ?
N4 C5 H5A 108.9 . . ?
N5 C5 H5A 108.9 . . ?
N4 C5 H5B 108.9 . . ?
N5 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
O5 C6 N5 125.54(15) . . ?
O5 C6 N6 125.59(16) . . ?
N5 C6 N6 108.85(14) . . ?
N6 C7 N7 114.05(14) . 2_666 ?
N6 C7 H7A 108.7 . . ?
N7 C7 H7A 108.7 2_666 . ?
N6 C7 H7B 108.7 . . ?
N7 C7 H7B 108.7 2_666 . ?
H7A C7 H7B 107.6 . . ?
O6 C8 N7 126.61(16) . . ?
O6 C8 N8 125.41(17) . . ?
N7 C8 N8 107.97(14) . . ?
N8 C9 N2 114.22(14) . . ?
N8 C9 C14 103.06(12) . . ?
N2 C9 C14 103.65(13) . . ?
N8 C9 H9 111.8 . . ?
N2 C9 H9 111.8 . . ?
C14 C9 H9 111.8 . . ?
N6 C10 N12 115.40(13) . . ?
N6 C10 C11 103.07(13) . . ?
N12 C10 C11 102.98(13) . . ?
N6 C10 H10 111.6 . . ?
N12 C10 H10 111.6 . . ?
C11 C10 H10 111.6 . . ?
N11 C11 N5 115.34(13) . . ?
N11 C11 C10 103.20(12) . . ?
N5 C11 C10 103.32(13) . . ?
N11 C11 H11 111.5 . . ?
N5 C11 H11 111.5 . . ?
C10 C11 H11 111.5 . . ?
N10 C12 N4 114.97(13) . . ?
N10 C12 C13 103.20(12) . . ?
N4 C12 C13 102.79(13) . . ?
N10 C12 H12 111.7 . . ?
N4 C12 H12 111.7 . . ?
C13 C12 H12 111.7 . . ?
N3 C13 N9 114.30(13) . . ?
N3 C13 C12 103.35(13) . . ?
N9 C13 C12 103.32(13) . . ?
N3 C13 H13 111.8 . . ?
N9 C13 H13 111.8 . . ?
C12 C13 H13 111.8 . . ?
N1 C14 N7 115.37(13) . . ?
N1 C14 C9 102.70(13) . . ?
N7 C14 C9 103.12(13) . . ?
N1 C14 H14 111.6 . . ?
N7 C14 H14 111.6 . . ?
C9 C14 H14 111.6 . . ?
N8 C15 N9 113.28(14) . . ?
N8 C15 H15A 108.9 . . ?
N9 C15 H15A 108.9 . . ?
N8 C15 H15B 108.9 . . ?
N9 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
O7 C16 N10 125.10(16) . . ?
O7 C16 N9 126.38(16) . . ?
N10 C16 N9 108.52(14) . . ?
N11 C17 N10 113.38(14) . . ?
N11 C17 H17A 108.9 . . ?
N10 C17 H17A 108.9 . . ?
N11 C17 H17B 108.9 . . ?
N10 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
O8 C18 N12 126.50(15) . . ?
O8 C18 N11 125.42(16) . . ?
N12 C18 N11 108.05(14) . . ?
H5W O3W H6W 112(2) . . ?
H7W O4W H8W 112.7(19) . . ?
H9W O5W H10W 111(2) . . ?
H11W O6W H12W 112(2) . . ?
H13W O7W H14W 110.9(19) . . ?
H15W O8W H16W 114(2) . . ?
H17W O9W H18W 114(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
C2 N1 C1 N12 -99.26(17) . . . 2_666 ?
C14 N1 C1 N12 85.84(19) . . . 2_666 ?
C3 N2 C2 O3 -13.0(3) . . . . ?
C9 N2 C2 O3 -176.38(15) . . . . ?
C3 N2 C2 N1 165.58(14) . . . . ?
C9 N2 C2 N1 2.22(18) . . . . ?
C1 N1 C2 O3 1.6(2) . . . . ?
C14 N1 C2 O3 176.98(15) . . . . ?
C1 N1 C2 N2 -177.06(14) . . . . ?
C14 N1 C2 N2 -1.64(18) . . . . ?
C4 N3 C3 N2 -107.87(18) . . . . ?
C13 N3 C3 N2 80.60(19) . . . . ?
C2 N2 C3 N3 108.36(18) . . . . ?
C9 N2 C3 N3 -90.22(19) . . . . ?
C3 N3 C4 O4 3.4(3) . . . . ?
C13 N3 C4 O4 175.66(15) . . . . ?
C3 N3 C4 N4 -174.92(14) . . . . ?
C13 N3 C4 N4 -2.63(18) . . . . ?
C5 N4 C4 O4 0.8(3) . . . . ?
C12 N4 C4 O4 -174.78(15) . . . . ?
C5 N4 C4 N3 179.06(14) . . . . ?
C12 N4 C4 N3 3.50(18) . . . . ?
C4 N4 C5 N5 102.64(18) . . . . ?
C12 N4 C5 N5 -82.25(19) . . . . ?
C6 N5 C5 N4 -112.10(17) . . . . ?
C11 N5 C5 N4 93.79(18) . . . . ?
C5 N5 C6 O5 11.1(3) . . . . ?
C11 N5 C6 O5 167.82(15) . . . . ?
C5 N5 C6 N6 -167.04(14) . . . . ?
C11 N5 C6 N6 -10.32(18) . . . . ?
C7 N6 C6 O5 2.5(3) . . . . ?
C10 N6 C6 O5 -171.91(15) . . . . ?
C7 N6 C6 N5 -179.36(14) . . . . ?
C10 N6 C6 N5 6.23(18) . . . . ?
C6 N6 C7 N7 101.97(18) . . . 2_666 ?
C10 N6 C7 N7 -84.24(19) . . . 2_666 ?
C7 N7 C8 O6 -3.8(3) 2_666 . . . ?
C14 N7 C8 O6 -174.75(17) . . . . ?
C7 N7 C8 N8 174.75(14) 2_666 . . . ?
C14 N7 C8 N8 3.79(19) . . . . ?
C15 N8 C8 O6 3.7(3) . . . . ?
C9 N8 C8 O6 174.67(17) . . . . ?
C15 N8 C8 N7 -174.84(15) . . . . ?
C9 N8 C8 N7 -3.89(19) . . . . ?
C8 N8 C9 N2 114.12(16) . . . . ?
C15 N8 C9 N2 -75.1(2) . . . . ?
C8 N8 C9 C14 2.41(18) . . . . ?
C15 N8 C9 C14 173.22(14) . . . . ?
C2 N2 C9 N8 -113.24(16) . . . . ?
C3 N2 C9 N8 83.76(19) . . . . ?
C2 N2 C9 C14 -1.88(17) . . . . ?
C3 N2 C9 C14 -164.89(14) . . . . ?
C6 N6 C10 N12 -111.43(16) . . . . ?
C7 N6 C10 N12 74.1(2) . . . . ?
C6 N6 C10 C11 0.02(17) . . . . ?
C7 N6 C10 C11 -174.41(14) . . . . ?
C18 N12 C10 N6 118.34(16) . . . . ?
C1 N12 C10 N6 -79.02(19) 2_666 . . . ?
C18 N12 C10 C11 6.85(18) . . . . ?
C1 N12 C10 C11 169.49(14) 2_666 . . . ?
C18 N11 C11 N5 -108.57(16) . . . . ?
C17 N11 C11 N5 71.4(2) . . . . ?
C18 N11 C11 C10 3.33(18) . . . . ?
C17 N11 C11 C10 -176.67(15) . . . . ?
C6 N5 C11 N11 121.71(15) . . . . ?
C5 N5 C11 N11 -81.85(18) . . . . ?
C6 N5 C11 C10 9.88(17) . . . . ?
C5 N5 C11 C10 166.32(14) . . . . ?
N6 C10 C11 N11 -126.17(13) . . . . ?
N12 C10 C11 N11 -5.81(16) . . . . ?
N6 C10 C11 N5 -5.68(15) . . . . ?
N12 C10 C11 N5 114.67(13) . . . . ?
C16 N10 C12 N4 111.49(16) . . . . ?
C17 N10 C12 N4 -81.6(2) . . . . ?
C16 N10 C12 C13 0.39(18) . . . . ?
C17 N10 C12 C13 167.29(15) . . . . ?
C4 N4 C12 N10 -114.21(16) . . . . ?
C5 N4 C12 N10 70.17(19) . . . . ?
C4 N4 C12 C13 -2.87(17) . . . . ?
C5 N4 C12 C13 -178.49(13) . . . . ?
C4 N3 C13 N9 112.32(16) . . . . ?
C3 N3 C13 N9 -75.28(19) . . . . ?
C4 N3 C13 C12 0.80(17) . . . . ?
C3 N3 C13 C12 173.20(13) . . . . ?
C16 N9 C13 N3 -114.79(16) . . . . ?
C15 N9 C13 N3 85.38(19) . . . . ?
C16 N9 C13 C12 -3.25(18) . . . . ?
C15 N9 C13 C12 -163.08(14) . . . . ?
N10 C12 C13 N3 121.03(13) . . . . ?
N4 C12 C13 N3 1.18(15) . . . . ?
N10 C12 C13 N9 1.64(16) . . . . ?
N4 C12 C13 N9 -118.21(13) . . . . ?
C2 N1 C14 N7 111.82(16) . . . . ?
C1 N1 C14 N7 -72.9(2) . . . . ?
C2 N1 C14 C9 0.44(17) . . . . ?
C1 N1 C14 C9 175.76(14) . . . . ?
C8 N7 C14 N1 -113.36(16) . . . . ?
C7 N7 C14 N1 76.0(2) 2_666 . . . ?
C8 N7 C14 C9 -2.23(18) . . . . ?
C7 N7 C14 C9 -172.86(15) 2_666 . . . ?
N8 C9 C14 N1 120.14(13) . . . . ?
N2 C9 C14 N1 0.82(15) . . . . ?
N8 C9 C14 N7 -0.10(16) . . . . ?
N2 C9 C14 N7 -119.41(13) . . . . ?
C8 N8 C15 N9 -108.73(18) . . . . ?
C9 N8 C15 N9 81.3(2) . . . . ?
C16 N9 C15 N8 110.86(18) . . . . ?
C13 N9 C15 N8 -91.05(19) . . . . ?
C17 N10 C16 O7 9.4(3) . . . . ?
C12 N10 C16 O7 176.75(16) . . . . ?
C17 N10 C16 N9 -169.83(14) . . . . ?
C12 N10 C16 N9 -2.43(19) . . . . ?
C15 N9 C16 O7 -15.3(3) . . . . ?
C13 N9 C16 O7 -175.53(17) . . . . ?
C15 N9 C16 N10 163.92(15) . . . . ?
C13 N9 C16 N10 3.63(19) . . . . ?
C18 N11 C17 N10 99.16(18) . . . . ?
C11 N11 C17 N10 -80.84(19) . . . . ?
C16 N10 C17 N11 -101.40(18) . . . . ?
C12 N10 C17 N11 92.79(18) . . . . ?
C1 N12 C18 O8 10.3(3) 2_666 . . . ?
C10 N12 C18 O8 173.20(16) . . . . ?
C1 N12 C18 N11 -167.95(14) 2_666 . . . ?
C10 N12 C18 N11 -5.08(19) . . . . ?
C11 N11 C18 O8 -177.50(16) . . . . ?
C17 N11 C18 O8 2.5(3) . . . . ?
C11 N11 C18 N12 0.80(19) . . . . ?
C17 N11 C18 N12 -179.20(15) . . . . ?

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
O1W H1W O5 0.851(9) 1.966(11) 2.8088(18) 170(2) 2_675
O1W H2W O3W 0.848(9) 1.781(10) 2.624(2) 173(3) .
O2W H3W O4W 0.848(9) 2.017(16) 2.7898(19) 151(2) 2_675
O2W H4W O4W 0.846(9) 1.905(11) 2.743(2) 171(3) .
O3W H5W Cl3 0.855(10) 2.327(12) 3.1625(16) 166(3) 1_455
O3W H6W O7W 0.846(10) 2.080(18) 2.857(2) 152(3) 2_566
O4W H7W Cl3 0.843(9) 2.244(10) 3.0815(14) 172(2) .
O4W H8W O4 0.845(9) 1.995(12) 2.7990(18) 159(2) .
O5W H9W O7 0.845(10) 1.800(11) 2.6316(19) 168(3) .
O5W H10W O6W 0.842(10) 1.880(11) 2.716(2) 172(3) .
O6W H11W O6 0.852(10) 1.879(14) 2.6972(19) 160(3) .
O6W H12W Cl3 0.848(10) 2.290(10) 3.1349(16) 174(3) 1_446
O7W H13W O4 0.850(9) 2.42(2) 2.9891(19) 125(2) 2_666
O7W H13W O5 0.850(9) 2.251(19) 2.9034(18) 134(2) 2_666
O7W H14W O6W 0.856(9) 1.908(13) 2.730(2) 160(3) .
O8W H15W O3 0.840(10) 2.007(18) 2.7019(19) 140(2) 2_666
O8W H15W O4 0.840(10) 2.54(2) 3.000(2) 115(2) 2_666
O8W H16W O7W 0.843(9) 1.838(10) 2.678(2) 175(3) .
O9W H17W O8 0.826(10) 1.844(16) 2.6139(19) 155(3) .
O9W H18W O5W 0.831(10) 1.654(11) 2.483(3) 175(3) .

_refine_diff_density_max         0.877
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.068




#=============================================================================#
#    Luis Cunha-Silva @ LAQV - REQUIMTE & DQB FCUP  *  28/02/2019  *   END    #
#=============================================================================#
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
