# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_B335-2ba
_database_code_depnum_ccdc_archive 'CCDC 2340732'
loop_
_audit_author_name
_audit_author_address
'Rahman Bikas'
;Imam Khomeini International University
Iran
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H26 Mn N12 O2 Zn2, 2(C H4 O)'
_chemical_formula_sum            'C42 H34 Mn N12 O4 Zn2'
_chemical_formula_weight         956.49

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   24.306(8)
_cell_length_b                   8.269(3)
_cell_length_c                   21.095(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4240(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3187
_cell_measurement_theta_min      1.6
_cell_measurement_theta_max      25

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_F_000             1948
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.473
_shelx_estimated_absorpt_T_min   0.710
_shelx_estimated_absorpt_T_max   0.891
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.707
_exptl_absorpt_correction_T_max  0.855
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5
Analytical numeric absorption correction using a
multifaceted crystal model based on expressions
derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, ccd camera Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16705
_diffrn_reflns_av_unetI/netI     0.0874
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.676
_diffrn_reflns_theta_max         30.738
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6077
_reflns_number_gt                3622
_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       'CrysAlis PRO (Agilent, 2004)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2004)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0476P)²+0.6556P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6077
_refine_ls_number_parameters     288
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1323
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.002
_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
Zn Zn 0.61755(2) 0.69645(5) 0.66533(2) 0.01969(12) Uani 1 1 d . . . . .
Mn Mn 0.5000 0.19660(8) 0.7500 0.01402(16) Uani 1 2 d S T P . .
O1 O 0.57649(10) 0.7236(3) 0.57784(12) 0.0262(6) Uani 1 1 d . . . . .
C1 C 0.58772(13) 0.7585(4) 0.46667(17) 0.0179(7) Uani 1 1 d . . . . .
C2 C 0.53266(14) 0.8039(4) 0.45994(17) 0.0222(7) Uani 1 1 d . . . . .
H2 H 0.5104 0.8230 0.4962 0.027 Uiso 1 1 calc R U . . .
C3 C 0.51130(14) 0.8205(4) 0.40020(17) 0.0223(8) Uani 1 1 d . . . . .
H3 H 0.4739 0.8525 0.3963 0.027 Uiso 1 1 calc R U . . .
N4 N 0.54015(11) 0.7941(3) 0.34669(13) 0.0200(6) Uani 1 1 d . . . . .
C5 C 0.59314(14) 0.7488(5) 0.35408(18) 0.0246(8) Uani 1 1 d . . . . .
H5 H 0.6144 0.7277 0.3172 0.029 Uiso 1 1 calc R U . . .
C6 C 0.61800(14) 0.7316(4) 0.41264(18) 0.0242(8) Uani 1 1 d . . . . .
H6 H 0.6556 0.7015 0.4155 0.029 Uiso 1 1 calc R U . . .
C7 C 0.61043(13) 0.7352(4) 0.53201(17) 0.0193(7) Uani 1 1 d . . . . .
N1 N 0.66519(11) 0.7252(3) 0.53561(14) 0.0206(6) Uani 1 1 d . . . . .
N2 N 0.67939(11) 0.6988(3) 0.59814(13) 0.0187(6) Uani 1 1 d . . . . .
C8 C 0.73089(14) 0.6836(4) 0.61447(17) 0.0194(7) Uani 1 1 d . . . . .
C11 C 0.73967(14) 0.6483(4) 0.68246(17) 0.0211(8) Uani 1 1 d . . . . .
N3 N 0.69483(12) 0.6629(3) 0.71992(15) 0.0248(7) Uani 1 1 d . . . . .
C31 C 0.69922(16) 0.6275(5) 0.78183(19) 0.0313(9) Uani 1 1 d . . . . .
H31 H 0.6676 0.6382 0.8079 0.038 Uiso 1 1 calc R U . . .
C41 C 0.74763(16) 0.5764(5) 0.8091(2) 0.0358(10) Uani 1 1 d . . . . .
H41 H 0.7495 0.5538 0.8532 0.043 Uiso 1 1 calc R U . . .
C51 C 0.79336(16) 0.5587(5) 0.77109(19) 0.0307(9) Uani 1 1 d . . . . .
H51 H 0.8271 0.5213 0.7885 0.037 Uiso 1 1 calc R U . . .
C61 C 0.78952(14) 0.5963(4) 0.70694(18) 0.0249(8) Uani 1 1 d . . . . .
H61 H 0.8208 0.5864 0.6802 0.030 Uiso 1 1 calc R U . . .
C12 C 0.77784(13) 0.6941(4) 0.56984(18) 0.0200(7) Uani 1 1 d . . . . .
C22 C 0.82314(13) 0.7908(4) 0.58540(19) 0.0246(8) Uani 1 1 d . . . . .
H22 H 0.8238 0.8460 0.6249 0.030 Uiso 1 1 calc R U . . .
C32 C 0.86692(15) 0.8071(5) 0.5442(2) 0.0316(9) Uani 1 1 d . . . . .
H32 H 0.8969 0.8758 0.5548 0.038 Uiso 1 1 calc R U . . .
C42 C 0.86695(16) 0.7227(5) 0.4874(2) 0.0371(10) Uani 1 1 d . . . . .
H42 H 0.8971 0.7327 0.4590 0.045 Uiso 1 1 calc R U . . .
C52 C 0.82290(15) 0.6237(5) 0.4722(2) 0.0347(10) Uani 1 1 d . . . . .
H52 H 0.8231 0.5652 0.4334 0.042 Uiso 1 1 calc R U . . .
C62 C 0.77875(15) 0.6093(5) 0.51289(18) 0.0268(8) Uani 1 1 d . . . . .
H62 H 0.7488 0.5411 0.5019 0.032 Uiso 1 1 calc R U . . .
N10 N 0.55961(12) 1.0080(4) 0.72164(14) 0.0231(7) Uani 1 1 d . . . . .
C10 C 0.58440(14) 0.8983(4) 0.70380(17) 0.0208(8) Uani 1 1 d . . . . .
N20 N 0.55842(12) 0.3798(3) 0.71472(14) 0.0225(7) Uani 1 1 d . . . . .
C20 C 0.58159(14) 0.4899(4) 0.69538(17) 0.0215(8) Uani 1 1 d . . . . .
O1M O 0.46768(15) 0.6185(5) 0.5943(2) 0.0421(14) Uani 0.736(7) 1 d D . P A 1
H1M H 0.4994 0.6399 0.5809 0.063 Uiso 0.736(7) 1 calc R U P A 1
C1M C 0.4575(4) 0.7077(12) 0.6517(8) 0.042(2) Uani 0.736(7) 1 d D . P A 1
H1M1 H 0.4766 0.6555 0.6871 0.063 Uiso 0.736(7) 1 calc R U P A 1
H1M2 H 0.4179 0.7097 0.6603 0.063 Uiso 0.736(7) 1 calc R U P A 1
H1M3 H 0.4710 0.8187 0.6468 0.063 Uiso 0.736(7) 1 calc R U P A 1
O2M O 0.4149(8) 0.814(2) 0.6524(8) 0.091(6) Uiso 0.264(7) 1 d D . P A 2
H2M H 0.3998 0.8156 0.6883 0.136 Uiso 0.264(7) 1 calc R U P A 2
C2M C 0.4495(15) 0.675(4) 0.648(3) 0.042(2) Uani 0.264(7) 1 d D . P A 2
H2M1 H 0.4824 0.7027 0.6233 0.063 Uiso 0.264(7) 1 calc R U P A 2
H2M2 H 0.4295 0.5878 0.6266 0.063 Uiso 0.264(7) 1 calc R U P A 2
H2M3 H 0.4603 0.6404 0.6905 0.063 Uiso 0.264(7) 1 calc R U P A 2


_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
Zn C20 2.021(4) . ?
Zn C10 2.023(4) . ?
Zn N2 2.066(3) . ?
Zn O1 2.110(3) . ?
Zn N3 2.221(3) . ?
Mn N20 2.206(3) 3_656 ?
Mn N20 2.206(3) . ?
Mn N10 2.211(3) 3_646 ?
Mn N10 2.211(3) 1_545 ?
Mn N4 2.262(3) 7_566 ?
Mn N4 2.262(3) 5_666 ?
O1 C7 1.274(4) . ?
C1 C6 1.375(5) . ?
C1 C2 1.397(5) . ?
C1 C7 1.497(5) . ?
C2 C3 1.370(5) . ?
C2 H2 0.9500 . ?
C3 N4 1.347(4) . ?
C3 H3 0.9500 . ?
N4 C5 1.350(4) . ?
N4 Mn 2.262(3) 5_666 ?
C5 C6 1.383(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.336(4) . ?
N1 N2 1.381(4) . ?
N2 C8 1.304(4) . ?
C8 C11 1.479(5) . ?
C8 C12 1.482(5) . ?
C11 N3 1.352(4) . ?
C11 C61 1.386(5) . ?
N3 C31 1.343(5) . ?
C31 C41 1.376(5) . ?
C31 H31 0.9500 . ?
C41 C51 1.378(5) . ?
C41 H41 0.9500 . ?
C51 C61 1.392(5) . ?
C51 H51 0.9500 . ?
C61 H61 0.9500 . ?
C12 C62 1.391(5) . ?
C12 C22 1.400(4) . ?
C22 C32 1.380(5) . ?
C22 H22 0.9500 . ?
C32 C42 1.387(6) . ?
C32 H32 0.9500 . ?
C42 C52 1.386(6) . ?
C42 H42 0.9500 . ?
C52 C62 1.379(5) . ?
C52 H52 0.9500 . ?
C62 H62 0.9500 . ?
N10 C10 1.152(4) . ?
N10 Mn 2.211(3) 1_565 ?
N20 C20 1.145(4) . ?
O1M C1M 1.440(14) . ?
O1M H1M 0.8400 . ?
C1M H1M1 0.9800 . ?
C1M H1M2 0.9800 . ?
C1M H1M3 0.9800 . ?
O2M C2M 1.423(19) . ?
O2M H2M 0.8400 . ?
C2M H2M1 0.9800 . ?
C2M H2M2 0.9800 . ?
C2M H2M3 0.9800 . ?

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
C20 Zn C10 113.53(14) . . ?
C20 Zn N2 122.53(12) . . ?
C10 Zn N2 123.86(12) . . ?
C20 Zn O1 99.20(12) . . ?
C10 Zn O1 94.28(12) . . ?
N2 Zn O1 75.11(10) . . ?
C20 Zn N3 95.59(12) . . ?
C10 Zn N3 103.41(13) . . ?
N2 Zn N3 75.02(12) . . ?
O1 Zn N3 150.10(11) . . ?
N20 Mn N20 93.25(15) 3_656 . ?
N20 Mn N10 88.35(11) 3_656 3_646 ?
N20 Mn N10 175.97(11) . 3_646 ?
N20 Mn N10 175.97(11) 3_656 1_545 ?
N20 Mn N10 88.35(11) . 1_545 ?
N10 Mn N10 90.30(16) 3_646 1_545 ?
N20 Mn N4 87.15(11) 3_656 7_566 ?
N20 Mn N4 90.18(11) . 7_566 ?
N10 Mn N4 93.60(11) 3_646 7_566 ?
N10 Mn N4 89.15(11) 1_545 7_566 ?
N20 Mn N4 90.18(11) 3_656 5_666 ?
N20 Mn N4 87.15(11) . 5_666 ?
N10 Mn N4 89.15(11) 3_646 5_666 ?
N10 Mn N4 93.60(11) 1_545 5_666 ?
N4 Mn N4 176.11(15) 7_566 5_666 ?
C7 O1 Zn 111.4(2) . . ?
C6 C1 C2 118.2(3) . . ?
C6 C1 C7 123.0(3) . . ?
C2 C1 C7 118.8(3) . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
N4 C3 C2 123.9(3) . . ?
N4 C3 H3 118.1 . . ?
C2 C3 H3 118.1 . . ?
C3 N4 C5 116.4(3) . . ?
C3 N4 Mn 121.7(2) . 5_666 ?
C5 N4 Mn 121.7(2) . 5_666 ?
N4 C5 C6 123.3(3) . . ?
N4 C5 H5 118.4 . . ?
C6 C5 H5 118.4 . . ?
C1 C6 C5 119.3(3) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
O1 C7 N1 126.7(3) . . ?
O1 C7 C1 118.0(3) . . ?
N1 C7 C1 115.3(3) . . ?
C7 N1 N2 108.3(3) . . ?
C8 N2 N1 120.5(3) . . ?
C8 N2 Zn 121.1(2) . . ?
N1 N2 Zn 118.3(2) . . ?
N2 C8 C11 114.4(3) . . ?
N2 C8 C12 124.4(3) . . ?
C11 C8 C12 121.1(3) . . ?
N3 C11 C61 121.0(3) . . ?
N3 C11 C8 115.7(3) . . ?
C61 C11 C8 123.3(3) . . ?
C31 N3 C11 119.0(3) . . ?
C31 N3 Zn 126.8(3) . . ?
C11 N3 Zn 113.0(2) . . ?
N3 C31 C41 122.8(4) . . ?
N3 C31 H31 118.6 . . ?
C41 C31 H31 118.6 . . ?
C31 C41 C51 118.7(4) . . ?
C31 C41 H41 120.7 . . ?
C51 C41 H41 120.7 . . ?
C41 C51 C61 119.2(3) . . ?
C41 C51 H51 120.4 . . ?
C61 C51 H51 120.4 . . ?
C11 C61 C51 119.4(3) . . ?
C11 C61 H61 120.3 . . ?
C51 C61 H61 120.3 . . ?
C62 C12 C22 118.5(3) . . ?
C62 C12 C8 122.1(3) . . ?
C22 C12 C8 119.4(3) . . ?
C32 C22 C12 121.0(4) . . ?
C32 C22 H22 119.5 . . ?
C12 C22 H22 119.5 . . ?
C22 C32 C42 119.7(4) . . ?
C22 C32 H32 120.2 . . ?
C42 C32 H32 120.2 . . ?
C52 C42 C32 119.8(4) . . ?
C52 C42 H42 120.1 . . ?
C32 C42 H42 120.1 . . ?
C62 C52 C42 120.5(4) . . ?
C62 C52 H52 119.7 . . ?
C42 C52 H52 119.7 . . ?
C52 C62 C12 120.4(4) . . ?
C52 C62 H62 119.8 . . ?
C12 C62 H62 119.8 . . ?
C10 N10 Mn 170.5(3) . 1_565 ?
N10 C10 Zn 171.4(3) . . ?
C20 N20 Mn 169.2(3) . . ?
N20 C20 Zn 174.9(3) . . ?
C1M O1M H1M 109.5 . . ?
O1M C1M H1M1 109.5 . . ?
O1M C1M H1M2 109.5 . . ?
H1M1 C1M H1M2 109.5 . . ?
O1M C1M H1M3 109.5 . . ?
H1M1 C1M H1M3 109.5 . . ?
H1M2 C1M H1M3 109.5 . . ?
C2M O2M H2M 109.5 . . ?
O2M C2M H2M1 109.5 . . ?
O2M C2M H2M2 109.5 . . ?
H2M1 C2M H2M2 109.5 . . ?
O2M C2M H2M3 109.5 . . ?
H2M1 C2M H2M3 109.5 . . ?
H2M2 C2M H2M3 109.5 . . ?

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
C6 C1 C2 C3 -0.3(5) . . . . ?
C7 C1 C2 C3 -178.0(3) . . . . ?
C1 C2 C3 N4 0.6(6) . . . . ?
C2 C3 N4 C5 0.0(5) . . . . ?
C2 C3 N4 Mn 174.7(3) . . . 5_666 ?
C3 N4 C5 C6 -1.0(5) . . . . ?
Mn N4 C5 C6 -175.7(3) 5_666 . . . ?
C2 C1 C6 C5 -0.5(5) . . . . ?
C7 C1 C6 C5 177.0(3) . . . . ?
N4 C5 C6 C1 1.2(6) . . . . ?
Zn O1 C7 N1 2.8(5) . . . . ?
Zn O1 C7 C1 -178.8(2) . . . . ?
C6 C1 C7 O1 -162.8(3) . . . . ?
C2 C1 C7 O1 14.7(5) . . . . ?
C6 C1 C7 N1 15.7(5) . . . . ?
C2 C1 C7 N1 -166.7(3) . . . . ?
O1 C7 N1 N2 0.3(5) . . . . ?
C1 C7 N1 N2 -178.1(3) . . . . ?
C7 N1 N2 C8 179.7(3) . . . . ?
C7 N1 N2 Zn -3.5(3) . . . . ?
N1 N2 C8 C11 -177.3(3) . . . . ?
Zn N2 C8 C11 6.0(4) . . . . ?
N1 N2 C8 C12 0.6(5) . . . . ?
Zn N2 C8 C12 -176.1(2) . . . . ?
N2 C8 C11 N3 -10.4(4) . . . . ?
C12 C8 C11 N3 171.6(3) . . . . ?
N2 C8 C11 C61 166.6(3) . . . . ?
C12 C8 C11 C61 -11.3(5) . . . . ?
C61 C11 N3 C31 0.6(5) . . . . ?
C8 C11 N3 C31 177.8(3) . . . . ?
C61 C11 N3 Zn -167.6(3) . . . . ?
C8 C11 N3 Zn 9.6(4) . . . . ?
C11 N3 C31 C41 -0.1(6) . . . . ?
Zn N3 C31 C41 166.3(3) . . . . ?
N3 C31 C41 C51 -0.9(6) . . . . ?
C31 C41 C51 C61 1.4(6) . . . . ?
N3 C11 C61 C51 -0.1(5) . . . . ?
C8 C11 C61 C51 -177.0(3) . . . . ?
C41 C51 C61 C11 -1.0(6) . . . . ?
N2 C8 C12 C62 -48.3(5) . . . . ?
C11 C8 C12 C62 129.5(4) . . . . ?
N2 C8 C12 C22 132.4(4) . . . . ?
C11 C8 C12 C22 -49.8(4) . . . . ?
C62 C12 C22 C32 2.5(5) . . . . ?
C8 C12 C22 C32 -178.2(3) . . . . ?
C12 C22 C32 C42 -2.0(5) . . . . ?
C22 C32 C42 C52 0.5(6) . . . . ?
C32 C42 C52 C62 0.5(6) . . . . ?
C42 C52 C62 C12 0.0(6) . . . . ?
C22 C12 C62 C52 -1.5(5) . . . . ?
C8 C12 C62 C52 179.2(3) . . . . ?

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
O1M H1M O1 0.84 2.00 2.805(5) 160.8 .

_refine_diff_density_max         0.961
_refine_diff_density_min         -0.820
_refine_diff_density_rms         0.105

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_b335-4ra
_database_code_depnum_ccdc_archive 'CCDC 2340736'
loop_
_audit_author_name
_audit_author_address
'Rahman Bikas'
;Imam Khomeini International University
Iran
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 N5 O4 Zn, C H4 O'
_chemical_formula_sum            'C19 H17 N5 O5 Zn'
_chemical_formula_weight         460.74

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.5902(18)
_cell_length_b                   12.838(3)
_cell_length_c                   17.558(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1936.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    80(2)
_cell_measurement_reflns_used    5438
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.480
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    1.312
_shelx_estimated_absorpt_T_min   0.543
_shelx_estimated_absorpt_T_max   0.622
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.601
_exptl_absorpt_correction_T_max  0.665
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      80(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, ccd camera Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8625
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.965
_diffrn_reflns_theta_max         30.182
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             5029
_reflns_number_gt                4793
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.688
_reflns_Friedel_fraction_max     0.819
_reflns_Friedel_fraction_full    0.958

_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       'CrysAlis CCD; Oxford-Diffraction Poland, 2003'
_computing_cell_refinement       'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_data_reduction        'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0402P)²+0.0676P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1832 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.046(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5029
_refine_ls_number_parameters     277
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0821
_refine_ls_wR_factor_gt          0.0806
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.099
_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
Zn Zn 0.36365(4) 0.37563(3) 0.76480(2) 0.01628(10) Uani 1 1 d . . . . .
O13 O 0.4982(4) 0.4038(2) 0.67229(14) 0.0372(7) Uani 1 1 d . . . . .
O23 O 0.6006(3) 0.2713(2) 0.72694(18) 0.0412(7) Uani 1 1 d . . . . .
N13 N 0.6011(4) 0.3354(3) 0.67329(19) 0.0346(8) Uani 1 1 d . . . . .
O33 O 0.7014(5) 0.3314(3) 0.62511(19) 0.0548(9) Uani 1 1 d . . . . .
C1 C 0.0689(3) 0.1132(2) 0.77023(16) 0.0122(5) Uani 1 1 d . . . . .
C2 C 0.0519(4) 0.0251(2) 0.81554(16) 0.0141(6) Uani 1 1 d . . . . .
H2 H 0.1269 0.0089 0.8535 0.017 Uiso 1 1 calc R U . . .
C3 C -0.0761(4) -0.0384(2) 0.80428(16) 0.0156(6) Uani 1 1 d . . . . .
H3 H -0.0872 -0.0987 0.8353 0.019 Uiso 1 1 calc R U . . .
N4 N -0.1849(3) -0.01883(19) 0.75169(13) 0.0144(5) Uani 1 1 d . . . . .
C5 C -0.1665(4) 0.0655(2) 0.70751(17) 0.0167(6) Uani 1 1 d . . . . .
H5 H -0.2431 0.0799 0.6700 0.020 Uiso 1 1 calc R U . . .
C6 C -0.0411(4) 0.1322(2) 0.71417(16) 0.0178(6) Uani 1 1 d . . . . .
H6 H -0.0304 0.1901 0.6809 0.021 Uiso 1 1 calc R U . . .
C7 C 0.1947(4) 0.1915(2) 0.78232(16) 0.0128(6) Uani 1 1 d . . . . .
O1 O 0.2258(2) 0.25214(15) 0.72760(12) 0.0147(4) Uani 1 1 d . . . . .
N1 N 0.2541(3) 0.19253(19) 0.85242(14) 0.0125(5) Uani 1 1 d . . . . .
N2 N 0.3493(3) 0.27880(18) 0.85784(13) 0.0133(5) Uani 1 1 d . . . . .
C8 C 0.4181(3) 0.3027(2) 0.92025(16) 0.0123(5) Uani 1 1 d . . . . .
C11 C 0.5029(3) 0.4034(2) 0.91774(16) 0.0119(6) Uani 1 1 d . . . . .
N3 N 0.4938(3) 0.4562(2) 0.85158(14) 0.0142(5) Uani 1 1 d . . . . .
C31 C 0.5661(4) 0.5480(2) 0.84515(18) 0.0168(6) Uani 1 1 d . . . . .
H31 H 0.5608 0.5840 0.7979 0.020 Uiso 1 1 calc R U . . .
C41 C 0.6485(4) 0.5929(2) 0.90464(17) 0.0183(6) Uani 1 1 d . . . . .
H41 H 0.6961 0.6593 0.8992 0.022 Uiso 1 1 calc R U . . .
C51 C 0.6594(4) 0.5377(3) 0.97247(17) 0.0185(6) Uani 1 1 d . . . . .
H51 H 0.7160 0.5658 1.0142 0.022 Uiso 1 1 calc R U . . .
C61 C 0.5872(3) 0.4414(2) 0.97906(16) 0.0142(6) Uani 1 1 d . . . . .
H61 H 0.5953 0.4022 1.0248 0.017 Uiso 1 1 calc R U . . .
C12 C 0.4144(3) 0.2391(2) 0.99068(17) 0.0137(6) Uani 1 1 d . . . . .
C22 C 0.3532(4) 0.2790(3) 1.05739(16) 0.0207(7) Uani 1 1 d . . . . .
H22 H 0.3136 0.3480 1.0585 0.025 Uiso 1 1 calc R U . . .
C32 C 0.3497(4) 0.2179(3) 1.12321(18) 0.0287(8) Uani 1 1 d . . . . .
H32 H 0.3028 0.2437 1.1684 0.034 Uiso 1 1 calc R U . . .
C42 C 0.4149(4) 0.1196(3) 1.1221(2) 0.0324(9) Uani 1 1 d . . . . .
H42 H 0.4162 0.0790 1.1673 0.039 Uiso 1 1 calc R U . . .
C52 C 0.4779(4) 0.0799(3) 1.0563(2) 0.0293(8) Uani 1 1 d . . . . .
H52 H 0.5228 0.0122 1.0563 0.035 Uiso 1 1 calc R U . . .
C62 C 0.4761(4) 0.1384(3) 0.98998(18) 0.0210(7) Uani 1 1 d . . . . .
H62 H 0.5168 0.1101 0.9441 0.025 Uiso 1 1 calc R U . . .
O1M O 0.8857(8) 0.7992(5) 0.9474(4) 0.0467(15) Uiso 0.5 1 d D . P A 1
H1M H 0.9251 0.7501 0.9725 0.070 Uiso 0.5 1 calc R U P A 1
C1M C 0.7755(13) 0.8487(9) 0.9909(8) 0.025(2) Uiso 0.5 1 d D . P A 1
H1M1 H 0.8256 0.8745 1.0373 0.037 Uiso 0.5 1 d R U P A 1
H1M2 H 0.6934 0.7991 1.0044 0.037 Uiso 0.5 1 d R U P A 1
H1M3 H 0.7300 0.9073 0.9629 0.037 Uiso 0.5 1 d R U P A 1
C2M C 0.746(3) 0.856(4) 0.994(3) 0.043(5) Uiso 0.25 1 d D . P B 2
H2M1 H 0.7726 0.8349 1.0459 0.065 Uiso 0.25 1 d R U P B 2
H2M2 H 0.7819 0.9272 0.9848 0.065 Uiso 0.25 1 d R U P B 2
H2M3 H 0.7978 0.8086 0.9577 0.065 Uiso 0.25 1 d R U P B 2
O2M O 0.5797(14) 0.8517(9) 0.9807(7) 0.038(3) Uiso 0.25 1 d D . P B 2
H2M H 0.5353 0.8544 1.0233 0.057 Uiso 0.25 1 d R U P B 2
C3M C 0.742(4) 0.863(3) 0.9836(19) 0.043(5) Uiso 0.25 1 d D . P C 3
H3M1 H 0.6688 0.9082 0.9566 0.065 Uiso 0.25 1 d R U P C 3
H3M2 H 0.7964 0.8184 0.9468 0.065 Uiso 0.25 1 d R U P C 3
H3M3 H 0.8174 0.9051 1.0115 0.065 Uiso 0.25 1 d R U P C 3
O3M O 0.6661(17) 0.7949(11) 1.0390(7) 0.050(3) Uiso 0.25 1 d D . P C 3
H3M H 0.7292 0.7589 1.0644 0.075 Uiso 0.25 1 d R U P C 3


_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
Zn O13 2.026(3) . ?
Zn N2 2.057(2) . ?
Zn N4 2.068(2) 3_556 ?
Zn O1 2.084(2) . ?
Zn N3 2.154(3) . ?
O13 N13 1.247(5) . ?
O23 N13 1.251(4) . ?
N13 O33 1.208(5) . ?
C1 C6 1.386(4) . ?
C1 C2 1.390(4) . ?
C1 C7 1.492(4) . ?
C2 C3 1.383(4) . ?
C2 H2 0.9500 . ?
C3 N4 1.338(4) . ?
C3 H3 0.9500 . ?
N4 C5 1.341(4) . ?
N4 Zn 2.068(2) 3_546 ?
C5 C6 1.381(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.265(3) . ?
C7 N1 1.333(4) . ?
N1 N2 1.380(3) . ?
N2 C8 1.282(4) . ?
C8 C12 1.483(4) . ?
C8 C11 1.484(4) . ?
C11 N3 1.347(4) . ?
C11 C61 1.386(4) . ?
N3 C31 1.338(4) . ?
C31 C41 1.387(4) . ?
C31 H31 0.9500 . ?
C41 C51 1.389(4) . ?
C41 H41 0.9500 . ?
C51 C61 1.389(4) . ?
C51 H51 0.9500 . ?
C61 H61 0.9500 . ?
C12 C22 1.382(4) . ?
C12 C62 1.398(4) . ?
C22 C32 1.397(4) . ?
C22 H22 0.9500 . ?
C32 C42 1.380(6) . ?
C32 H32 0.9500 . ?
C42 C52 1.374(6) . ?
C42 H42 0.9500 . ?
C52 C62 1.386(4) . ?
C52 H52 0.9500 . ?
C62 H62 0.9500 . ?
O1M C1M 1.372(12) . ?
O1M H1M 0.8400 . ?
C1M H1M1 0.9800 . ?
C1M H1M2 0.9800 . ?
C1M H1M3 0.9800 . ?
C2M O2M 1.45(2) . ?
C2M H2M1 0.9800 . ?
C2M H2M2 0.9800 . ?
C2M H2M3 0.9800 . ?
O2M H2M 0.8400 . ?
C3M O3M 1.46(2) . ?
C3M H3M1 0.9800 . ?
C3M H3M2 0.9800 . ?
C3M H3M3 0.9800 . ?
O3M H3M 0.8400 . ?

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
O13 Zn N2 141.17(12) . . ?
O13 Zn N4 101.21(11) . 3_556 ?
N2 Zn N4 117.55(10) . 3_556 ?
O13 Zn O1 102.05(10) . . ?
N2 Zn O1 75.82(9) . . ?
N4 Zn O1 91.86(9) 3_556 . ?
O13 Zn N3 100.69(11) . . ?
N2 Zn N3 76.08(10) . . ?
N4 Zn N3 99.78(10) 3_556 . ?
O1 Zn N3 151.86(9) . . ?
N13 O13 Zn 105.5(2) . . ?
O33 N13 O13 121.7(4) . . ?
O33 N13 O23 120.2(4) . . ?
O13 N13 O23 118.1(3) . . ?
C6 C1 C2 118.6(3) . . ?
C6 C1 C7 118.4(3) . . ?
C2 C1 C7 122.9(3) . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
N4 C3 C2 122.9(3) . . ?
N4 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
C3 N4 C5 118.0(3) . . ?
C3 N4 Zn 119.5(2) . 3_546 ?
C5 N4 Zn 122.3(2) . 3_546 ?
N4 C5 C6 122.9(3) . . ?
N4 C5 H5 118.5 . . ?
C6 C5 H5 118.5 . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
O1 C7 N1 127.9(3) . . ?
O1 C7 C1 117.4(3) . . ?
N1 C7 C1 114.6(2) . . ?
C7 O1 Zn 110.49(18) . . ?
C7 N1 N2 107.4(2) . . ?
C8 N2 N1 121.6(2) . . ?
C8 N2 Zn 120.4(2) . . ?
N1 N2 Zn 117.77(17) . . ?
N2 C8 C12 124.8(3) . . ?
N2 C8 C11 114.2(3) . . ?
C12 C8 C11 121.0(2) . . ?
N3 C11 C61 121.6(3) . . ?
N3 C11 C8 115.8(2) . . ?
C61 C11 C8 122.7(3) . . ?
C31 N3 C11 119.3(3) . . ?
C31 N3 Zn 127.2(2) . . ?
C11 N3 Zn 113.5(2) . . ?
N3 C31 C41 122.6(3) . . ?
N3 C31 H31 118.7 . . ?
C41 C31 H31 118.7 . . ?
C31 C41 C51 118.0(3) . . ?
C31 C41 H41 121.0 . . ?
C51 C41 H41 121.0 . . ?
C61 C51 C41 119.7(3) . . ?
C61 C51 H51 120.1 . . ?
C41 C51 H51 120.1 . . ?
C11 C61 C51 118.8(3) . . ?
C11 C61 H61 120.6 . . ?
C51 C61 H61 120.6 . . ?
C22 C12 C62 119.6(3) . . ?
C22 C12 C8 120.7(3) . . ?
C62 C12 C8 119.6(3) . . ?
C12 C22 C32 120.1(3) . . ?
C12 C22 H22 120.0 . . ?
C32 C22 H22 120.0 . . ?
C42 C32 C22 119.5(3) . . ?
C42 C32 H32 120.3 . . ?
C22 C32 H32 120.3 . . ?
C52 C42 C32 120.8(3) . . ?
C52 C42 H42 119.6 . . ?
C32 C42 H42 119.6 . . ?
C42 C52 C62 120.0(4) . . ?
C42 C52 H52 120.0 . . ?
C62 C52 H52 120.0 . . ?
C52 C62 C12 119.9(3) . . ?
C52 C62 H62 120.1 . . ?
C12 C62 H62 120.1 . . ?
C1M O1M H1M 109.5 . . ?
O1M C1M H1M1 108.5 . . ?
O1M C1M H1M2 109.3 . . ?
H1M1 C1M H1M2 109.5 . . ?
O1M C1M H1M3 110.6 . . ?
H1M1 C1M H1M3 109.5 . . ?
H1M2 C1M H1M3 109.5 . . ?
O2M C2M H2M1 111.4 . . ?
O2M C2M H2M2 108.3 . . ?
H2M1 C2M H2M2 109.5 . . ?
O2M C2M H2M3 108.7 . . ?
H2M1 C2M H2M3 109.5 . . ?
H2M2 C2M H2M3 109.5 . . ?
C2M O2M H2M 107.8 . . ?
O3M C3M H3M1 113.3 . . ?
O3M C3M H3M2 108.0 . . ?
H3M1 C3M H3M2 109.5 . . ?
O3M C3M H3M3 107.1 . . ?
H3M1 C3M H3M3 109.5 . . ?
H3M2 C3M H3M3 109.5 . . ?
C3M O3M H3M 113.3 . . ?

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
Zn O13 N13 O33 -179.5(3) . . . . ?
Zn O13 N13 O23 -1.1(4) . . . . ?
C6 C1 C2 C3 -1.7(4) . . . . ?
C7 C1 C2 C3 174.4(3) . . . . ?
C1 C2 C3 N4 -0.1(4) . . . . ?
C2 C3 N4 C5 1.1(4) . . . . ?
C2 C3 N4 Zn 176.1(2) . . . 3_546 ?
C3 N4 C5 C6 -0.1(4) . . . . ?
Zn N4 C5 C6 -174.9(2) 3_546 . . . ?
N4 C5 C6 C1 -1.8(5) . . . . ?
C2 C1 C6 C5 2.6(4) . . . . ?
C7 C1 C6 C5 -173.7(3) . . . . ?
C6 C1 C7 O1 -22.2(4) . . . . ?
C2 C1 C7 O1 161.6(3) . . . . ?
C6 C1 C7 N1 153.8(3) . . . . ?
C2 C1 C7 N1 -22.4(4) . . . . ?
N1 C7 O1 Zn -9.0(4) . . . . ?
C1 C7 O1 Zn 166.40(19) . . . . ?
O1 C7 N1 N2 5.0(4) . . . . ?
C1 C7 N1 N2 -170.6(2) . . . . ?
C7 N1 N2 C8 177.1(3) . . . . ?
C7 N1 N2 Zn 2.1(3) . . . . ?
N1 N2 C8 C12 4.6(5) . . . . ?
Zn N2 C8 C12 179.5(2) . . . . ?
N1 N2 C8 C11 -174.3(2) . . . . ?
Zn N2 C8 C11 0.6(3) . . . . ?
N2 C8 C11 N3 1.2(4) . . . . ?
C12 C8 C11 N3 -177.8(3) . . . . ?
N2 C8 C11 C61 -178.6(3) . . . . ?
C12 C8 C11 C61 2.5(4) . . . . ?
C61 C11 N3 C31 -0.8(4) . . . . ?
C8 C11 N3 C31 179.4(3) . . . . ?
C61 C11 N3 Zn 177.5(2) . . . . ?
C8 C11 N3 Zn -2.3(3) . . . . ?
C11 N3 C31 C41 -1.3(5) . . . . ?
Zn N3 C31 C41 -179.3(2) . . . . ?
N3 C31 C41 C51 2.1(5) . . . . ?
C31 C41 C51 C61 -0.7(5) . . . . ?
N3 C11 C61 C51 2.1(4) . . . . ?
C8 C11 C61 C51 -178.2(3) . . . . ?
C41 C51 C61 C11 -1.2(5) . . . . ?
N2 C8 C12 C22 -119.4(4) . . . . ?
C11 C8 C12 C22 59.5(4) . . . . ?
N2 C8 C12 C62 61.9(4) . . . . ?
C11 C8 C12 C62 -119.3(3) . . . . ?
C62 C12 C22 C32 -1.6(5) . . . . ?
C8 C12 C22 C32 179.6(3) . . . . ?
C12 C22 C32 C42 3.3(5) . . . . ?
C22 C32 C42 C52 -2.4(5) . . . . ?
C32 C42 C52 C62 -0.2(6) . . . . ?
C42 C52 C62 C12 2.0(5) . . . . ?
C22 C12 C62 C52 -1.0(5) . . . . ?
C8 C12 C62 C52 177.7(3) . . . . ?

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
C3 H3 O1M 0.95 2.38 3.281(7) 158.9 1_445
O3M H3M O33 0.84 1.68 2.493(14) 160.6 2_665

_refine_diff_density_max         0.461
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.070

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_b2881a
_database_code_depnum_ccdc_archive 'CCDC 2340733'
loop_
_audit_author_name
_audit_author_address
'Rahman Bikas'
;Imam Khomeini International University
Iran
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C39.49 H26 Cl0.51 Mn N11.49 O2 Zn2, 2(C H4 O)'
_chemical_formula_sum            'C41.49 H34 Cl0.51 Mn N11.49 O4 Zn2'
_chemical_formula_weight         961.30

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   24.344(6)
_cell_length_b                   8.2169(18)
_cell_length_c                   21.057(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4212.1(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5787
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      25

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_F_000             1956
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.514
_shelx_estimated_absorpt_T_min   0.659
_shelx_estimated_absorpt_T_max   0.901
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_detector_area_resol_mean 10.3456
_diffrn_measurement_method       'omega scan'
_diffrn_reflns_number            19539
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.789
_diffrn_reflns_theta_max         30.854
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5985
_reflns_number_gt                4706
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0344P)²+3.7998P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     'direct methods'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5985
_refine_ls_number_parameters     300
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.0998
_refine_ls_wR_factor_gt          0.0926
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.000
_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
Zn Zn 0.11732(2) 0.30105(7) 0.16593(2) 0.01935(12) Uani 0.971(2) 1 d . . P B .
Zn1 Zn 0.1026(7) 0.247(2) 0.1747(6) 0.01935(12) Uani 0.029(2) 1 d . . P B .
Mn Mn 0.0000 -0.19816(6) 0.2500 0.01618(11) Uani 1 2 d S T P . .
C1 C 0.23886(9) 0.3499(3) 0.18361(11) 0.0209(5) Uani 1 1 d . . . . .
N2 N 0.19404(8) 0.3347(3) 0.22073(10) 0.0257(5) Uani 1 1 d . . . . .
C3 C 0.19832(11) 0.3704(4) 0.28254(12) 0.0333(6) Uani 1 1 d . . . . .
H3 H 0.1665 0.3604 0.3084 0.040 Uiso 1 1 calc R U . . .
C4 C 0.24671(12) 0.4211(4) 0.31061(13) 0.0387(7) Uani 1 1 d . . . . .
H4 H 0.2484 0.4427 0.3549 0.046 Uiso 1 1 calc R U . . .
C5 C 0.29242(11) 0.4393(4) 0.27279(13) 0.0341(6) Uani 1 1 d . . . . .
H5 H 0.3260 0.4768 0.2905 0.041 Uiso 1 1 calc R U . . .
C6 C 0.28896(10) 0.4024(3) 0.20827(12) 0.0267(5) Uani 1 1 d . . . . .
H6 H 0.3202 0.4129 0.1816 0.032 Uiso 1 1 calc R U . . .
C7 C 0.23023(9) 0.3151(3) 0.11471(11) 0.0201(5) Uani 1 1 d . . . . .
C11 C 0.27731(9) 0.3048(3) 0.07060(11) 0.0215(5) Uani 1 1 d . . . . .
C21 C 0.32259(10) 0.2074(3) 0.08670(13) 0.0267(5) Uani 1 1 d . . . . .
H21 H 0.3231 0.1516 0.1262 0.032 Uiso 1 1 calc R U . . .
C31 C 0.36659(11) 0.1923(4) 0.04513(15) 0.0346(6) Uani 1 1 d . . . . .
H31 H 0.3968 0.1246 0.0558 0.042 Uiso 1 1 calc R U . . .
C41 C 0.36626(11) 0.2760(4) -0.01166(15) 0.0382(7) Uani 1 1 d . . . . .
H41 H 0.3963 0.2657 -0.0401 0.046 Uiso 1 1 calc R U . . .
C51 C 0.32216(11) 0.3750(4) -0.02735(13) 0.0350(6) Uani 1 1 d . . . . .
H51 H 0.3225 0.4334 -0.0663 0.042 Uiso 1 1 calc R U . . .
C61 C 0.27749(10) 0.3897(3) 0.01335(12) 0.0274(5) Uani 1 1 d . . . . .
H61 H 0.2473 0.4571 0.0022 0.033 Uiso 1 1 calc R U . . .
N3 N 0.17897(8) 0.2988(2) 0.09903(9) 0.0195(4) Uani 1 1 d . . . . .
N4 N 0.16453(8) 0.2729(2) 0.03666(9) 0.0204(4) Uani 1 1 d . . . . .
C71 C 0.10997(9) 0.2625(3) 0.03274(11) 0.0208(5) Uani 1 1 d . . . . .
O1 O 0.07613(7) 0.2726(2) 0.07853(8) 0.0293(4) Uani 1 1 d . . . . .
C12 C 0.08696(9) 0.2399(3) -0.03248(11) 0.0199(5) Uani 1 1 d . . . . .
C22 C 0.03219(9) 0.1951(3) -0.03964(11) 0.0234(5) Uani 1 1 d . . . . .
H22 H 0.0098 0.1757 -0.0035 0.028 Uiso 1 1 calc R U . . .
C32 C 0.01091(10) 0.1793(3) -0.09991(11) 0.0231(5) Uani 1 1 d . . . . .
H32 H -0.0264 0.1469 -0.1042 0.028 Uiso 1 1 calc R U . . .
N42 N 0.04000(8) 0.2070(3) -0.15283(9) 0.0215(4) Uani 1 1 d . . . . .
C52 C 0.09288(10) 0.2513(3) -0.14535(11) 0.0238(5) Uani 1 1 d . . . . .
H52 H 0.1141 0.2722 -0.1823 0.029 Uiso 1 1 calc R U . . .
C62 C 0.11781(9) 0.2677(3) -0.08691(11) 0.0238(5) Uani 1 1 d . . . . .
H62 H 0.1554 0.2975 -0.0839 0.029 Uiso 1 1 calc R U . . .
N10 N 0.05736(12) -0.3807(4) 0.21579(12) 0.0219(6) Uani 0.872(6) 1 d . . P B .
C10 C 0.08166(13) -0.4961(5) 0.19550(14) 0.0193(6) Uani 0.872(6) 1 d . . P . .
N20 N 0.05947(12) -0.0115(4) 0.22222(13) 0.0217(6) Uani 0.872(6) 1 d . . P B .
C20 C 0.08479(12) 0.1002(5) 0.20422(14) 0.0193(7) Uani 0.872(6) 1 d . . P B .
O1M O 0.03259(11) 0.3783(4) 0.40599(14) 0.0438(10) Uani 0.712(6) 1 d D . P A 1
H1M H 0.0001 0.3573 0.4168 0.066 Uiso 0.712(6) 1 calc R U P A 1
C1M C 0.04481(18) 0.2971(8) 0.3497(2) 0.0326(13) Uani 0.712(6) 1 d D . P A 1
H1M1 H 0.0252 0.3489 0.3144 0.049 Uiso 0.712(6) 1 calc R U P A 1
H1M2 H 0.0334 0.1831 0.3532 0.049 Uiso 0.712(6) 1 calc R U P A 1
H1M3 H 0.0845 0.3022 0.3419 0.049 Uiso 0.712(6) 1 calc R U P A 1
O2M O 0.0854(5) 0.1920(14) 0.3486(6) 0.083(4) Uiso 0.288(6) 1 d D . P A 2
H2M H 0.1040 0.1981 0.3151 0.125 Uiso 0.288(6) 1 d R U P A 2
C2M C 0.0399(12) 0.292(4) 0.3552(18) 0.139(14) Uiso 0.288(6) 1 d D . P A 2
H2M1 H 0.0134 0.2706 0.3892 0.209 Uiso 0.288(6) 1 d R U P A 2
H2M2 H 0.0208 0.2924 0.3142 0.209 Uiso 0.288(6) 1 d R U P A 2
H2M3 H 0.0574 0.3977 0.3622 0.209 Uiso 0.288(6) 1 d R U P A 2
Cl1 Cl 0.0743(5) -0.4273(14) 0.2040(6) 0.057(4) Uiso 0.128(6) 1 d . . P B 2
Cl2 Cl 0.0756(4) 0.0395(13) 0.2178(5) 0.045(3) Uiso 0.128(6) 1 d . . P B 2


_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
Zn Zn1 0.60(2) . ?
Zn C10 1.980(4) 1_565 ?
Zn C20 2.000(4) . ?
Zn N3 2.058(2) . ?
Zn O1 2.1089(17) . ?
Zn N2 2.213(2) . ?
Zn Cl1 2.593(11) 1_565 ?
Zn Cl2 2.616(10) . ?
Zn1 C20 1.43(2) . ?
Zn1 Cl2 2.04(2) . ?
Zn1 O1 2.136(12) . ?
Zn1 C10 2.213(16) 1_565 ?
Zn1 N3 2.485(19) . ?
Mn N10 2.172(4) 3 ?
Mn N10 2.172(4) . ?
Mn N20 2.189(4) . ?
Mn N20 2.189(4) 3 ?
Mn N42 2.2671(19) 5 ?
Mn N42 2.2671(19) 7_556 ?
Mn Cl2 2.768(10) . ?
Mn Cl2 2.768(10) 3 ?
Mn Cl1 2.785(11) 3 ?
Mn Cl1 2.785(11) . ?
C1 N2 1.348(3) . ?
C1 C6 1.394(3) . ?
C1 C7 1.494(3) . ?
N2 C3 1.338(3) . ?
C3 C4 1.382(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N3 1.298(3) . ?
C7 C11 1.478(3) . ?
C11 C61 1.393(3) . ?
C11 C21 1.403(3) . ?
C21 C31 1.389(4) . ?
C21 H21 0.9500 . ?
C31 C41 1.379(4) . ?
C31 H31 0.9500 . ?
C41 C51 1.387(4) . ?
C41 H41 0.9500 . ?
C51 C61 1.390(4) . ?
C51 H51 0.9500 . ?
C61 H61 0.9500 . ?
N3 N4 1.376(3) . ?
N4 C71 1.334(3) . ?
C71 O1 1.271(3) . ?
C71 C12 1.495(3) . ?
C12 C62 1.389(3) . ?
C12 C22 1.392(3) . ?
C22 C32 1.377(3) . ?
C22 H22 0.9500 . ?
C32 N42 1.340(3) . ?
C32 H32 0.9500 . ?
N42 C52 1.347(3) . ?
N42 Mn 2.2672(19) 5 ?
C52 C62 1.379(3) . ?
C52 H52 0.9500 . ?
C62 H62 0.9500 . ?
N10 Cl1 0.615(10) . ?
N10 C10 1.196(6) . ?
C10 Cl1 0.620(10) . ?
C10 Zn 1.980(4) 1_545 ?
C10 Zn1 2.213(16) 1_545 ?
N20 Cl2 0.582(9) . ?
N20 C20 1.169(7) . ?
C20 Cl2 0.617(9) . ?
O1M C1M 1.392(6) . ?
O1M H1M 0.8400 . ?
C1M H1M1 0.9800 . ?
C1M H1M2 0.9800 . ?
C1M H1M3 0.9800 . ?
O2M C2M 1.386(18) . ?
O2M H2M 0.8400 . ?
C2M H2M1 0.9800 . ?
C2M H2M2 0.9800 . ?
C2M H2M3 0.9800 . ?
Cl1 Zn 2.593(11) 1_545 ?

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
C10 Zn C20 113.22(12) 1_565 . ?
C10 Zn N3 122.86(11) 1_565 . ?
C20 Zn N3 123.85(10) . . ?
C10 Zn O1 99.18(10) 1_565 . ?
C20 Zn O1 94.13(10) . . ?
N3 Zn O1 75.42(7) . . ?
C10 Zn N2 95.79(10) 1_565 . ?
C20 Zn N2 103.13(10) . . ?
N3 Zn N2 75.09(8) . . ?
O1 Zn N2 150.49(8) . . ?
C20 Zn Cl1 115.2(3) . 1_565 ?
N3 Zn Cl1 120.9(3) . 1_565 ?
O1 Zn Cl1 100.0(3) . 1_565 ?
N2 Zn Cl1 94.1(3) . 1_565 ?
C10 Zn Cl2 113.0(3) 1_565 . ?
C20 Zn Cl2 1.0(3) . . ?
N3 Zn Cl2 124.2(2) . . ?
O1 Zn Cl2 95.1(3) . . ?
N2 Zn Cl2 102.3(3) . . ?
N10 Mn N10 92.65(14) 3 . ?
N10 Mn N20 176.11(9) 3 . ?
N10 Mn N20 88.29(10) . . ?
N10 Mn N20 88.29(10) 3 3 ?
N10 Mn N20 176.11(9) . 3 ?
N20 Mn N20 91.02(14) . 3 ?
N10 Mn N42 90.06(8) 3 5 ?
N10 Mn N42 87.40(8) . 5 ?
N20 Mn N42 93.75(9) . 5 ?
N20 Mn N42 88.83(8) 3 5 ?
N10 Mn N42 87.40(8) 3 7_556 ?
N10 Mn N42 90.06(8) . 7_556 ?
N20 Mn N42 88.83(8) . 7_556 ?
N20 Mn N42 93.75(9) 3 7_556 ?
N42 Mn N42 176.32(11) 5 7_556 ?
N10 Mn Cl2 174.8(2) 3 . ?
N10 Mn Cl2 88.8(2) . . ?
N20 Mn Cl2 1.3(3) . . ?
N20 Mn Cl2 90.6(2) 3 . ?
N42 Mn Cl2 95.0(2) 5 . ?
N42 Mn Cl2 87.6(2) 7_556 . ?
N10 Mn Cl2 88.8(2) 3 3 ?
N10 Mn Cl2 174.8(2) . 3 ?
N20 Mn Cl2 90.6(2) . 3 ?
N20 Mn Cl2 1.3(3) 3 3 ?
N42 Mn Cl2 87.6(2) 5 3 ?
N42 Mn Cl2 95.0(2) 7_556 3 ?
Cl2 Mn Cl2 90.3(4) . 3 ?
N10 Mn Cl1 1.3(3) 3 3 ?
N10 Mn Cl1 93.8(2) . 3 ?
N20 Mn Cl1 175.1(2) . 3 ?
N20 Mn Cl1 87.2(3) 3 3 ?
N42 Mn Cl1 90.8(2) 5 3 ?
N42 Mn Cl1 86.8(2) 7_556 3 ?
Cl2 Mn Cl1 173.8(3) . 3 ?
Cl2 Mn Cl1 87.7(3) 3 3 ?
N10 Mn Cl1 93.8(2) 3 . ?
N20 Mn Cl1 87.2(3) . . ?
N20 Mn Cl1 175.1(2) 3 . ?
N42 Mn Cl1 86.8(2) 5 . ?
N42 Mn Cl1 90.8(2) 7_556 . ?
Cl2 Mn Cl1 87.7(3) . . ?
Cl2 Mn Cl1 173.8(3) 3 . ?
Cl1 Mn Cl1 94.9(5) 3 . ?
N2 C1 C6 121.4(2) . . ?
N2 C1 C7 115.6(2) . . ?
C6 C1 C7 123.0(2) . . ?
C3 N2 C1 118.7(2) . . ?
C3 N2 Zn 126.90(18) . . ?
C1 N2 Zn 113.10(15) . . ?
N2 C3 C4 123.3(3) . . ?
N2 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
C5 C4 C3 118.3(3) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 119.4(2) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 118.9(2) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
N3 C7 C11 125.4(2) . . ?
N3 C7 C1 113.7(2) . . ?
C11 C7 C1 120.8(2) . . ?
C61 C11 C21 119.5(2) . . ?
C61 C11 C7 121.2(2) . . ?
C21 C11 C7 119.3(2) . . ?
C31 C21 C11 120.3(3) . . ?
C31 C21 H21 119.9 . . ?
C11 C21 H21 119.9 . . ?
C41 C31 C21 119.8(3) . . ?
C41 C31 H31 120.1 . . ?
C21 C31 H31 120.1 . . ?
C31 C41 C51 120.2(3) . . ?
C31 C41 H41 119.9 . . ?
C51 C41 H41 119.9 . . ?
C41 C51 C61 120.6(3) . . ?
C41 C51 H51 119.7 . . ?
C61 C51 H51 119.7 . . ?
C51 C61 C11 119.5(3) . . ?
C51 C61 H61 120.2 . . ?
C11 C61 H61 120.2 . . ?
C7 N3 N4 120.29(19) . . ?
C7 N3 Zn 121.73(16) . . ?
N4 N3 Zn 117.93(14) . . ?
C71 N4 N3 108.87(18) . . ?
O1 C71 N4 126.5(2) . . ?
O1 C71 C12 117.5(2) . . ?
N4 C71 C12 116.0(2) . . ?
C71 O1 Zn 111.18(14) . . ?
C62 C12 C22 118.2(2) . . ?
C62 C12 C71 122.4(2) . . ?
C22 C12 C71 119.4(2) . . ?
C32 C22 C12 119.0(2) . . ?
C32 C22 H22 120.5 . . ?
C12 C22 H22 120.5 . . ?
N42 C32 C22 123.5(2) . . ?
N42 C32 H32 118.3 . . ?
C22 C32 H32 118.3 . . ?
C32 N42 C52 117.0(2) . . ?
C32 N42 Mn 121.20(15) . 5 ?
C52 N42 Mn 121.65(15) . 5 ?
N42 C52 C62 123.5(2) . . ?
N42 C52 H52 118.3 . . ?
C62 C52 H52 118.3 . . ?
C52 C62 C12 118.8(2) . . ?
C52 C62 H62 120.6 . . ?
C12 C62 H62 120.6 . . ?
C10 N10 Mn 169.6(2) . . ?
N10 C10 Zn 175.1(3) . 1_545 ?
C20 N20 Mn 170.3(2) . . ?
C1M O1M H1M 109.5 . . ?
O1M C1M H1M1 109.5 . . ?
O1M C1M H1M2 109.5 . . ?
H1M1 C1M H1M2 109.5 . . ?
O1M C1M H1M3 109.5 . . ?
H1M1 C1M H1M3 109.5 . . ?
H1M2 C1M H1M3 109.5 . . ?
C2M O2M H2M 118.6 . . ?
O2M C2M H2M1 119.6 . . ?
O2M C2M H2M2 107.1 . . ?
H2M1 C2M H2M2 109.5 . . ?
O2M C2M H2M3 101.1 . . ?
H2M1 C2M H2M3 109.5 . . ?
H2M2 C2M H2M3 109.5 . . ?

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
C3 H3 O2M 0.95 2.56 3.411(12) 150.0 .
C6 H6 Cl2 0.95 2.85 3.490(11) 126.0 8_665
C52 H52 Cl1 0.95 2.88 3.516(12) 125.3 7
O1M H1M O1 0.84 1.99 2.805(3) 164.8 3
O2M H2M Cl2 0.84 2.52 3.035(16) 120.3 .
C2M H2M1 O1 0.98 2.28 3.15(3) 147.7 3

_refine_diff_density_max         0.447
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.074

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_b335-3ra
_database_code_depnum_ccdc_archive 'CCDC 2340734'
loop_
_audit_author_name
_audit_author_address
'Rahman Bikas'
;Imam Khomeini International University
Iran
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 Br N4 O Zn'
_chemical_formula_sum            'C18 H13 Br N4 O Zn'
_chemical_formula_weight         446.60

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'
Zn Zn 0.2839 1.4301 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.7892(19)
_cell_length_b                   13.133(3)
_cell_length_c                   16.077(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1855.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    80(2)
_cell_measurement_reflns_used    1458
_cell_measurement_theta_min      2
_cell_measurement_theta_max      20

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    3.489
_shelx_estimated_absorpt_T_min   0.641
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.745
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      80(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, ccd camera Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4979
_diffrn_reflns_av_unetI/netI     0.3110
_diffrn_reflns_av_R_equivalents  0.1156
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_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         2.002
_diffrn_reflns_theta_max         25.540
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.916
_reflns_number_total             3173
_reflns_number_gt                1378
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.601
_reflns_Friedel_fraction_max     0.807
_reflns_Friedel_fraction_full    0.810

_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       'CrysAlis CCD; Oxford-Diffraction Poland, 2003'
_computing_cell_refinement       'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_data_reduction        'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 261 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.03(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3173
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2154
_refine_ls_R_factor_gt           0.0940
_refine_ls_wR_factor_ref         0.1826
_refine_ls_wR_factor_gt          0.1313
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_refine_ls_shift/su_max          0.000
_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
Zn Zn 0.6489(3) 0.60513(16) 0.2465(2) 0.0263(7) Uani 1 1 d . . . . .
Br Br 0.4928(3) 0.56695(18) 0.36304(17) 0.0464(8) Uani 1 1 d . . . . .
O1 O 0.7807(15) 0.7280(9) 0.2905(9) 0.018(3) Uani 1 1 d . . . . .
C1 C 0.916(2) 0.8768(12) 0.2451(17) 0.018(3) Uani 1 1 d . . . . .
C2 C 0.924(2) 0.9620(13) 0.1995(14) 0.018(3) Uani 1 1 d . . . . .
H2 H 0.8443 0.9771 0.1612 0.022 Uiso 1 1 calc R U . . .
C3 C 1.046(2) 1.0292(14) 0.2076(13) 0.018(3) Uani 1 1 d . . . . .
H3 H 1.0504 1.0879 0.1731 0.021 Uiso 1 1 calc R U . . .
N4 N 1.1566(19) 1.0130(10) 0.2620(12) 0.018(3) Uani 1 1 d . . . . .
C5 C 1.146(2) 0.9287(15) 0.3128(15) 0.035(7) Uani 1 1 d . . . . .
H5 H 1.2218 0.9182 0.3539 0.042 Uiso 1 1 calc R U . . .
C6 C 1.030(2) 0.8595(13) 0.3067(14) 0.021(3) Uani 1 1 d . . . . .
H6 H 1.0256 0.8018 0.3423 0.025 Uiso 1 1 calc R U . . .
C7 C 0.804(2) 0.7908(14) 0.2317(15) 0.021(3) Uani 1 1 d . . . . .
N1 N 0.7496(19) 0.7893(12) 0.1548(12) 0.021(3) Uani 1 1 d . . . . .
N2 N 0.654(2) 0.7054(11) 0.1475(12) 0.021(3) Uani 1 1 d . . . . .
C8 C 0.612(2) 0.6751(14) 0.0725(15) 0.021(3) Uani 1 1 d . . . . .
C11 C 0.520(2) 0.5814(13) 0.0788(13) 0.021(3) Uani 1 1 d . . . . .
N3 N 0.520(2) 0.5282(10) 0.1476(11) 0.021(3) Uani 1 1 d . . . . .
C31 C 0.445(2) 0.4392(14) 0.1542(15) 0.027(3) Uani 1 1 d . . . . .
H31 H 0.4451 0.4017 0.2047 0.033 Uiso 1 1 calc R U . . .
C41 C 0.367(2) 0.4041(15) 0.0856(14) 0.027(3) Uani 1 1 d . . . . .
H41 H 0.3175 0.3399 0.0892 0.033 Uiso 1 1 calc R U . . .
C51 C 0.357(3) 0.4561(14) 0.0141(14) 0.027(3) Uani 1 1 d . . . . .
H51 H 0.2984 0.4326 -0.0318 0.033 Uiso 1 1 calc R U . . .
C61 C 0.438(2) 0.5477(14) 0.0120(15) 0.027(3) Uani 1 1 d . . . . .
H61 H 0.4365 0.5875 -0.0373 0.033 Uiso 1 1 calc R U . . .
C12 C 0.643(3) 0.7289(15) -0.0062(15) 0.027(3) Uani 1 1 d . . . . .
C22 C 0.718(2) 0.6774(16) -0.0652(15) 0.027(3) Uani 1 1 d . . . . .
H22 H 0.7474 0.6089 -0.0547 0.032 Uiso 1 1 calc R U . . .
C32 C 0.756(2) 0.7209(16) -0.1413(16) 0.027(3) Uani 1 1 d . . . . .
H32 H 0.8180 0.6845 -0.1795 0.032 Uiso 1 1 calc R U . . .
C42 C 0.704(2) 0.8168(15) -0.1618(16) 0.027(3) Uani 1 1 d . . . . .
H42 H 0.7209 0.8464 -0.2149 0.032 Uiso 1 1 calc R U . . .
C52 C 0.621(3) 0.8687(17) -0.0977(16) 0.036(7) Uani 1 1 d . . . . .
H52 H 0.5870 0.9360 -0.1089 0.043 Uiso 1 1 calc R U . . .
C62 C 0.588(2) 0.8281(14) -0.0215(15) 0.023(6) Uani 1 1 d . . . . .
H62 H 0.5319 0.8647 0.0191 0.027 Uiso 1 1 calc R U . . .


_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
Zn N2 2.066(17) . ?
Zn N4 2.099(15) 3_745 ?
Zn O1 2.108(12) . ?
Zn N3 2.198(17) . ?
Zn Br 2.375(4) . ?
O1 C7 1.27(2) . ?
C1 C2 1.34(3) . ?
C1 C6 1.43(3) . ?
C1 C7 1.51(2) . ?
C2 C3 1.40(2) . ?
C2 H2 0.9500 . ?
C3 N4 1.32(2) . ?
C3 H3 0.9500 . ?
N4 C5 1.38(2) . ?
N4 Zn 2.099(15) 3_755 ?
C5 C6 1.37(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.33(3) . ?
N1 N2 1.39(2) . ?
N2 C8 1.32(3) . ?
C8 C11 1.47(3) . ?
C8 C12 1.47(3) . ?
C11 N3 1.31(2) . ?
C11 C61 1.37(3) . ?
N3 C31 1.35(2) . ?
C31 C41 1.38(3) . ?
C31 H31 0.9500 . ?
C41 C51 1.34(3) . ?
C41 H41 0.9500 . ?
C51 C61 1.40(3) . ?
C51 H51 0.9500 . ?
C61 H61 0.9500 . ?
C12 C22 1.34(3) . ?
C12 C62 1.41(3) . ?
C22 C32 1.39(3) . ?
C22 H22 0.9500 . ?
C32 C42 1.38(3) . ?
C32 H32 0.9500 . ?
C42 C52 1.43(3) . ?
C42 H42 0.9500 . ?
C52 C62 1.37(3) . ?
C52 H52 0.9500 . ?
C62 H62 0.9500 . ?

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
N2 Zn N4 107.5(7) . 3_745 ?
N2 Zn O1 76.1(6) . . ?
N4 Zn O1 90.9(6) 3_745 . ?
N2 Zn N3 75.3(7) . . ?
N4 Zn N3 96.2(6) 3_745 . ?
O1 Zn N3 151.3(6) . . ?
N2 Zn Br 139.0(5) . . ?
N4 Zn Br 113.6(5) 3_745 . ?
O1 Zn Br 102.4(4) . . ?
N3 Zn Br 100.1(5) . . ?
C7 O1 Zn 109.7(13) . . ?
C2 C1 C6 118.7(18) . . ?
C2 C1 C7 125(2) . . ?
C6 C1 C7 115.8(17) . . ?
C1 C2 C3 121(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
N4 C3 C2 121.7(18) . . ?
N4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 N4 C5 118.0(18) . . ?
C3 N4 Zn 117.5(13) . 3_755 ?
C5 N4 Zn 124.0(15) . 3_755 ?
C6 C5 N4 123(2) . . ?
C6 C5 H5 118.6 . . ?
N4 C5 H5 118.6 . . ?
C5 C6 C1 117.7(18) . . ?
C5 C6 H6 121.1 . . ?
C1 C6 H6 121.1 . . ?
O1 C7 N1 128.6(19) . . ?
O1 C7 C1 119(2) . . ?
N1 C7 C1 112(2) . . ?
C7 N1 N2 108.0(17) . . ?
C8 N2 N1 118.9(18) . . ?
C8 N2 Zn 120.4(13) . . ?
N1 N2 Zn 116.9(14) . . ?
N2 C8 C11 109.9(19) . . ?
N2 C8 C12 126.0(19) . . ?
C11 C8 C12 124(2) . . ?
N3 C11 C61 119(2) . . ?
N3 C11 C8 120(2) . . ?
C61 C11 C8 120(2) . . ?
C11 N3 C31 122(2) . . ?
C11 N3 Zn 111.4(13) . . ?
C31 N3 Zn 126.6(15) . . ?
N3 C31 C41 118(2) . . ?
N3 C31 H31 120.9 . . ?
C41 C31 H31 120.9 . . ?
C51 C41 C31 123(2) . . ?
C51 C41 H41 118.4 . . ?
C31 C41 H41 118.4 . . ?
C41 C51 C61 115(2) . . ?
C41 C51 H51 122.4 . . ?
C61 C51 H51 122.4 . . ?
C11 C61 C51 122(2) . . ?
C11 C61 H61 119.0 . . ?
C51 C61 H61 119.0 . . ?
C22 C12 C62 121(2) . . ?
C22 C12 C8 117(2) . . ?
C62 C12 C8 122(2) . . ?
C12 C22 C32 122(2) . . ?
C12 C22 H22 118.9 . . ?
C32 C22 H22 118.9 . . ?
C42 C32 C22 120(2) . . ?
C42 C32 H32 119.8 . . ?
C22 C32 H32 119.8 . . ?
C32 C42 C52 116(2) . . ?
C32 C42 H42 122.2 . . ?
C52 C42 H42 122.2 . . ?
C62 C52 C42 124(2) . . ?
C62 C52 H52 117.8 . . ?
C42 C52 H52 117.8 . . ?
C52 C62 C12 116(2) . . ?
C52 C62 H62 121.8 . . ?
C12 C62 H62 121.8 . . ?

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
C3 H3 O1 0.95 2.44 3.02(2) 119.8 3_755

_refine_diff_density_max         1.448
_refine_diff_density_min         -0.952
_refine_diff_density_rms         0.163

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_ftco22
_database_code_depnum_ccdc_archive 'CCDC 2340735'
loop_
_audit_author_name
_audit_author_address
'Rahman Bikas'
;Imam Khomeini International University
Iran
;
_audit_update_record             
;
2024-03-15 deposited with the CCDC.	2024-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 O4'
_chemical_formula_sum            'C10 H10 O4'
_chemical_formula_weight         194.18

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   14.446(4)
_cell_length_b                   5.5867(18)
_cell_length_c                   21.823(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1761.2(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4767
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      22

_exptl_crystal_description       irregular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_T_min  0.681
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.42a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.855
_oxdiff_exptl_absorpt_empirical_full_max 1.178
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            13456
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.866
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.949
_reflns_number_total             4831
_reflns_number_gt                4316
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_max     0.880
_reflns_Friedel_fraction_full    0.895

_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       'CrysAlisPro 1.171.42.42a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.42a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.42a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0598P)²+1.0874P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     'direct methods'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1741 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4831
_refine_ls_number_parameters     343
_refine_ls_number_restraints     205
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.1438
_refine_ls_wR_factor_gt          0.1396
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.002
_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
C1A C 0.5064(2) 0.3073(6) 0.22754(14) 0.0058(6) Uani 0.796(4) 1 d D . P A 1
C2A C 0.5270(3) 0.1166(6) 0.18864(16) 0.0101(7) Uani 0.796(4) 1 d D . P A 1
H2A H 0.5680 -0.0063 0.2016 0.012 Uiso 0.796(4) 1 calc R U P A 1
C3A C 0.4869(3) 0.1075(7) 0.13047(17) 0.0144(8) Uani 0.796(4) 1 d D . P A 1
H3A H 0.5004 -0.0228 0.1039 0.017 Uiso 0.796(4) 1 calc R U P A 1
C4A C 0.4275(3) 0.2881(8) 0.11117(19) 0.0159(9) Uani 0.796(4) 1 d D . P A 1
H4A H 0.4017 0.2842 0.0711 0.019 Uiso 0.796(4) 1 calc R U P A 1
C5A C 0.4061(3) 0.4743(7) 0.15088(16) 0.0138(8) Uani 0.796(4) 1 d D . P A 1
H5A H 0.3639 0.5950 0.1382 0.017 Uiso 0.796(4) 1 calc R U P A 1
C6A C 0.4456(2) 0.4866(6) 0.20911(16) 0.0097(7) Uani 0.796(4) 1 d D . P A 1
H6A H 0.4312 0.6156 0.2358 0.012 Uiso 0.796(4) 1 calc R U P A 1
O1A O 0.5495(2) 0.3034(5) 0.28362(13) 0.0120(6) Uani 0.796(4) 1 d D . P A 1
C7A C 0.5309(3) 0.4973(6) 0.32430(14) 0.0093(7) Uani 0.796(4) 1 d D . P A 1
H7A1 H 0.4638 0.5061 0.3332 0.011 Uiso 0.796(4) 1 calc R U P A 1
H7A2 H 0.5504 0.6505 0.3055 0.011 Uiso 0.796(4) 1 calc R U P A 1
C8A C 0.5846(2) 0.4528(6) 0.38256(14) 0.0118(7) Uani 0.796(4) 1 d D . P A 1
H8A H 0.6521 0.4340 0.3736 0.014 Uiso 0.796(4) 1 calc R U P A 1
O2A O 0.5485(4) 0.2411(6) 0.41230(17) 0.0131(10) Uani 0.796(4) 1 d D . P A 1
C9A C 0.5016(3) 0.3005(8) 0.46315(18) 0.0166(8) Uani 0.796(4) 1 d D . P A 1
O3A O 0.4596(3) 0.1628(7) 0.49458(18) 0.0315(9) Uani 0.796(4) 1 d D . P A 1
O4A O 0.5051(2) 0.5387(5) 0.47325(15) 0.0196(7) Uani 0.796(4) 1 d D . P A 1
C10A C 0.5689(3) 0.6494(6) 0.43047(16) 0.0151(8) Uani 0.796(4) 1 d D . P A 1
H10A H 0.6276 0.6938 0.4509 0.018 Uiso 0.796(4) 1 calc R U P A 1
H10B H 0.5413 0.7940 0.4116 0.018 Uiso 0.796(4) 1 calc R U P A 1
C1C C 0.5020(11) 0.193(3) 0.2262(6) 0.031(5) Uiso 0.204(4) 1 d DG . P A 2
C2C C 0.4436(14) 0.008(3) 0.2084(7) 0.055(7) Uiso 0.204(4) 1 d DG . P A 2
H2C H 0.4336 -0.1246 0.2349 0.065 Uiso 0.204(4) 1 calc R U P A 2
C3C C 0.3998(14) 0.016(3) 0.1517(8) 0.062(8) Uiso 0.204(4) 1 d DG . P A 2
H3C H 0.3599 -0.1102 0.1395 0.075 Uiso 0.204(4) 1 calc R U P A 2
C4C C 0.4145(15) 0.210(4) 0.1129(7) 0.042(8) Uiso 0.204(4) 1 d DG . P A 2
H4C H 0.3845 0.2156 0.0742 0.050 Uiso 0.204(4) 1 calc R U P A 2
C5C C 0.4729(16) 0.395(3) 0.1307(7) 0.080(11) Uiso 0.204(4) 1 d DG . P A 2
H5C H 0.4829 0.5270 0.1042 0.096 Uiso 0.204(4) 1 calc R U P A 2
C6C C 0.5167(13) 0.386(3) 0.1874(7) 0.047(6) Uiso 0.204(4) 1 d DG . P A 2
H6C H 0.5566 0.5126 0.1996 0.056 Uiso 0.204(4) 1 calc R U P A 2
O1C O 0.5374(16) 0.200(3) 0.2846(7) 0.059(7) Uiso 0.204(4) 1 d D . P A 2
C7C C 0.523(2) 0.002(4) 0.3242(8) 0.060(8) Uiso 0.204(4) 1 d D . P A 2
H7C1 H 0.5446 -0.1475 0.3047 0.072 Uiso 0.204(4) 1 calc R U P A 2
H7C2 H 0.4557 -0.0155 0.3333 0.072 Uiso 0.204(4) 1 calc R U P A 2
C8C C 0.5759(13) 0.050(3) 0.3824(7) 0.076(11) Uiso 0.204(4) 1 d D . P A 2
H8C H 0.6435 0.0650 0.3735 0.091 Uiso 0.204(4) 1 calc R U P A 2
O2C O 0.542(2) 0.266(3) 0.4110(10) 0.072(14) Uiso 0.204(4) 1 d D . P A 2
C9C C 0.498(3) 0.215(3) 0.4637(14) 0.079(17) Uiso 0.204(4) 1 d D . P A 2
O3C O 0.452(2) 0.356(4) 0.4918(14) 0.108(11) Uiso 0.204(4) 1 d D . P A 2
O4C O 0.4967(14) -0.023(3) 0.4738(9) 0.061(6) Uiso 0.204(4) 1 d D . P A 2
C10C C 0.5593(16) -0.141(3) 0.4316(7) 0.048(6) Uiso 0.204(4) 1 d D . P A 2
H10C H 0.5305 -0.2860 0.4138 0.058 Uiso 0.204(4) 1 calc R U P A 2
H10D H 0.6178 -0.1861 0.4521 0.058 Uiso 0.204(4) 1 calc R U P A 2
C1B C 0.7526(3) 0.1940(7) 0.77254(16) 0.0127(7) Uani 0.832(4) 1 d D . P B 3
C2B C 0.6930(2) 0.0121(6) 0.79068(17) 0.0144(7) Uani 0.832(4) 1 d D . P B 3
H2B H 0.6784 -0.1157 0.7636 0.017 Uiso 0.832(4) 1 calc R U P B 3
C3B C 0.6548(3) 0.0213(6) 0.84976(17) 0.0155(7) Uani 0.832(4) 1 d D . P B 3
H3B H 0.6136 -0.1014 0.8626 0.019 Uiso 0.832(4) 1 calc R U P B 3
C4B C 0.6761(3) 0.2057(8) 0.88961(18) 0.0148(8) Uani 0.832(4) 1 d D . P B 3
H4B H 0.6505 0.2083 0.9297 0.018 Uiso 0.832(4) 1 calc R U P B 3
C5B C 0.7352(2) 0.3873(6) 0.87046(16) 0.0130(7) Uani 0.832(4) 1 d D . P B 3
H5B H 0.7497 0.5149 0.8976 0.016 Uiso 0.832(4) 1 calc R U P B 3
C6B C 0.7732(3) 0.3838(6) 0.81191(16) 0.0127(7) Uani 0.832(4) 1 d D . P B 3
H6B H 0.8128 0.5094 0.7988 0.015 Uiso 0.832(4) 1 calc R U P B 3
O1B O 0.7962(2) 0.2012(6) 0.71650(13) 0.0128(6) Uani 0.832(4) 1 d D . P B 3
C7B C 0.7785(3) 0.0108(6) 0.67499(14) 0.0112(7) Uani 0.832(4) 1 d D . P B 3
H7B1 H 0.7115 0.0014 0.6658 0.013 Uiso 0.832(4) 1 calc R U P B 3
H7B2 H 0.7983 -0.1434 0.6930 0.013 Uiso 0.832(4) 1 calc R U P B 3
C8B C 0.8325(2) 0.0616(5) 0.61715(14) 0.0096(6) Uani 0.832(4) 1 d D . P B 3
H8B H 0.8997 0.0836 0.6268 0.012 Uiso 0.832(4) 1 calc R U P B 3
O2B O 0.7957(3) 0.2741(7) 0.58816(15) 0.0151(9) Uani 0.832(4) 1 d D . P B 3
C9B C 0.7526(3) 0.2178(7) 0.53576(19) 0.0177(9) Uani 0.832(4) 1 d D . P B 3
O3B O 0.7104(3) 0.3552(6) 0.50478(16) 0.0258(7) Uani 0.832(4) 1 d D . P B 3
O4B O 0.7605(2) -0.0172(5) 0.52307(14) 0.0198(6) Uani 0.832(4) 1 d D . P B 3
C10B C 0.8200(3) -0.1315(6) 0.56799(15) 0.0153(8) Uani 0.832(4) 1 d D . P B 3
H10E H 0.8802 -0.1768 0.5496 0.018 Uiso 0.832(4) 1 calc R U P B 3
H10F H 0.7903 -0.2763 0.5853 0.018 Uiso 0.832(4) 1 calc R U P B 3
C1D C 0.7611(17) 0.281(4) 0.7698(7) 0.080(18) Uiso 0.168(4) 1 d DG . P B 4
C2D C 0.7835(15) 0.098(3) 0.8103(7) 0.053(8) Uiso 0.168(4) 1 d DG . P B 4
H2D H 0.8241 -0.0262 0.7978 0.063 Uiso 0.168(4) 1 calc R U P B 4
C3D C 0.7466(13) 0.097(3) 0.8691(6) 0.024(4) Uiso 0.168(4) 1 d DG . P B 4
H3D H 0.7619 -0.0277 0.8968 0.029 Uiso 0.168(4) 1 calc R U P B 4
C4D C 0.6872(14) 0.280(3) 0.8874(6) 0.025(7) Uiso 0.168(4) 1 d DG . P B 4
H4D H 0.6620 0.2790 0.9276 0.030 Uiso 0.168(4) 1 calc R U P B 4
C5D C 0.6648(15) 0.463(3) 0.8469(8) 0.048(8) Uiso 0.168(4) 1 d DG . P B 4
H5D H 0.6242 0.5873 0.8595 0.058 Uiso 0.168(4) 1 calc R U P B 4
C6D C 0.7017(16) 0.464(3) 0.7881(8) 0.063(10) Uiso 0.168(4) 1 d DG . P B 4
H6D H 0.6864 0.5888 0.7605 0.075 Uiso 0.168(4) 1 calc R U P B 4
O1D O 0.8100(14) 0.298(3) 0.7161(7) 0.034(5) Uiso 0.168(4) 1 d D . P B 4
C7D C 0.7897(18) 0.491(3) 0.6755(7) 0.040(7) Uiso 0.168(4) 1 d D . P B 4
H7D1 H 0.8092 0.6447 0.6937 0.048 Uiso 0.168(4) 1 calc R U P B 4
H7D2 H 0.7223 0.4977 0.6672 0.048 Uiso 0.168(4) 1 calc R U P B 4
C8D C 0.8422(10) 0.444(2) 0.6168(5) 0.022(4) Uiso 0.168(4) 1 d D . P B 4
H8D H 0.9094 0.4184 0.6258 0.026 Uiso 0.168(4) 1 calc R U P B 4
O2D O 0.804(2) 0.236(2) 0.5865(9) 0.060(16) Uiso 0.168(4) 1 d D . P B 4
C9D C 0.756(4) 0.302(3) 0.5368(17) 0.10(2) Uiso 0.168(4) 1 d D . P B 4
O3D O 0.7138(13) 0.167(3) 0.5046(9) 0.035(4) Uiso 0.168(4) 1 d D . P B 4
O4D O 0.7696(12) 0.535(2) 0.5239(7) 0.034(4) Uiso 0.168(4) 1 d D . P B 4
C10D C 0.8301(15) 0.642(3) 0.5692(6) 0.033(6) Uiso 0.168(4) 1 d D . P B 4
H10G H 0.8013 0.7862 0.5877 0.040 Uiso 0.168(4) 1 calc R U P B 4
H10H H 0.8903 0.6878 0.5509 0.040 Uiso 0.168(4) 1 calc R U P B 4


_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
C1A O1A 1.374(3) . ?
C1A C6A 1.391(4) . ?
C1A C2A 1.395(3) . ?
C2A C3A 1.396(4) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.390(4) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.389(4) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.395(4) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
O1A C7A 1.426(3) . ?
C7A C8A 1.510(4) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8A O2A 1.446(4) . ?
C8A C10A 1.533(4) . ?
C8A H8A 1.0000 . ?
O2A C9A 1.342(4) . ?
C9A O3A 1.196(4) . ?
C9A O4A 1.350(4) . ?
O4A C10A 1.450(4) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C1C O1C 1.372(5) . ?
C1C C2C 1.3900 . ?
C1C C6C 1.3900 . ?
C2C C3C 1.3900 . ?
C2C H2C 0.9500 . ?
C3C C4C 1.3900 . ?
C3C H3C 0.9500 . ?
C4C C5C 1.3900 . ?
C4C H4C 0.9500 . ?
C5C C6C 1.3900 . ?
C5C H5C 0.9500 . ?
C6C H6C 0.9500 . ?
O1C C7C 1.421(6) . ?
C7C C8C 1.511(7) . ?
C7C H7C1 0.9900 . ?
C7C H7C2 0.9900 . ?
C8C O2C 1.444(7) . ?
C8C C10C 1.531(6) . ?
C8C H8C 1.0000 . ?
O2C C9C 1.341(6) . ?
C9C O3C 1.196(6) . ?
C9C O4C 1.348(7) . ?
O4C C10C 1.450(6) . ?
C10C H10C 0.9900 . ?
C10C H10D 0.9900 . ?
C1B O1B 1.376(3) . ?
C1B C2B 1.390(4) . ?
C1B C6B 1.396(4) . ?
C2B C3B 1.403(4) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.383(4) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.391(4) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.391(4) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
O1B C7B 1.420(3) . ?
C7B C8B 1.511(4) . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?
C8B O2B 1.446(4) . ?
C8B C10B 1.532(4) . ?
C8B H8B 1.0000 . ?
O2B C9B 1.339(4) . ?
C9B O3B 1.191(4) . ?
C9B O4B 1.346(4) . ?
O4B C10B 1.452(3) . ?
C10B H10E 0.9900 . ?
C10B H10F 0.9900 . ?
C1D O1D 1.372(5) . ?
C1D C2D 1.3900 . ?
C1D C6D 1.3900 . ?
C2D C3D 1.3900 . ?
C2D H2D 0.9500 . ?
C3D C4D 1.3900 . ?
C3D H3D 0.9500 . ?
C4D C5D 1.3900 . ?
C4D H4D 0.9500 . ?
C5D C6D 1.3900 . ?
C5D H5D 0.9500 . ?
C6D H6D 0.9500 . ?
O1D C7D 1.422(6) . ?
C7D C8D 1.511(6) . ?
C7D H7D1 0.9900 . ?
C7D H7D2 0.9900 . ?
C8D O2D 1.446(6) . ?
C8D C10D 1.530(6) . ?
C8D H8D 1.0000 . ?
O2D C9D 1.341(6) . ?
C9D O3D 1.196(6) . ?
C9D O4D 1.348(7) . ?
O4D C10D 1.449(6) . ?
C10D H10G 0.9900 . ?
C10D H10H 0.9900 . ?

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
O1A C1A C6A 123.7(3) . . ?
O1A C1A C2A 115.6(3) . . ?
C6A C1A C2A 120.6(3) . . ?
C1A C2A C3A 119.5(3) . . ?
C1A C2A H2A 120.2 . . ?
C3A C2A H2A 120.2 . . ?
C4A C3A C2A 120.3(3) . . ?
C4A C3A H3A 119.8 . . ?
C2A C3A H3A 119.8 . . ?
C5A C4A C3A 119.5(3) . . ?
C5A C4A H4A 120.3 . . ?
C3A C4A H4A 120.3 . . ?
C4A C5A C6A 120.9(3) . . ?
C4A C5A H5A 119.5 . . ?
C6A C5A H5A 119.5 . . ?
C1A C6A C5A 119.1(3) . . ?
C1A C6A H6A 120.5 . . ?
C5A C6A H6A 120.5 . . ?
C1A O1A C7A 117.2(3) . . ?
O1A C7A C8A 107.6(3) . . ?
O1A C7A H7A1 110.2 . . ?
C8A C7A H7A1 110.2 . . ?
O1A C7A H7A2 110.2 . . ?
C8A C7A H7A2 110.2 . . ?
H7A1 C7A H7A2 108.5 . . ?
O2A C8A C7A 109.1(3) . . ?
O2A C8A C10A 103.1(2) . . ?
C7A C8A C10A 112.4(3) . . ?
O2A C8A H8A 110.7 . . ?
C7A C8A H8A 110.7 . . ?
C10A C8A H8A 110.7 . . ?
C9A O2A C8A 110.5(3) . . ?
O3A C9A O2A 124.8(4) . . ?
O3A C9A O4A 124.0(4) . . ?
O2A C9A O4A 111.1(3) . . ?
C9A O4A C10A 109.8(3) . . ?
O4A C10A C8A 103.2(2) . . ?
O4A C10A H10A 111.1 . . ?
C8A C10A H10A 111.1 . . ?
O4A C10A H10B 111.1 . . ?
C8A C10A H10B 111.1 . . ?
H10A C10A H10B 109.1 . . ?
O1C C1C C2C 120.6(6) . . ?
O1C C1C C6C 119.0(6) . . ?
C2C C1C C6C 120.0 . . ?
C1C C2C C3C 120.0 . . ?
C1C C2C H2C 120.0 . . ?
C3C C2C H2C 120.0 . . ?
C4C C3C C2C 120.0 . . ?
C4C C3C H3C 120.0 . . ?
C2C C3C H3C 120.0 . . ?
C5C C4C C3C 120.0 . . ?
C5C C4C H4C 120.0 . . ?
C3C C4C H4C 120.0 . . ?
C4C C5C C6C 120.0 . . ?
C4C C5C H5C 120.0 . . ?
C6C C5C H5C 120.0 . . ?
C5C C6C C1C 120.0 . . ?
C5C C6C H6C 120.0 . . ?
C1C C6C H6C 120.0 . . ?
C1C O1C C7C 119.0(8) . . ?
O1C C7C C8C 107.2(8) . . ?
O1C C7C H7C1 110.3 . . ?
C8C C7C H7C1 110.3 . . ?
O1C C7C H7C2 110.3 . . ?
C8C C7C H7C2 110.3 . . ?
H7C1 C7C H7C2 108.5 . . ?
O2C C8C C7C 109.7(9) . . ?
O2C C8C C10C 103.0(6) . . ?
C7C C8C C10C 112.7(9) . . ?
O2C C8C H8C 110.4 . . ?
C7C C8C H8C 110.4 . . ?
C10C C8C H8C 110.4 . . ?
C9C O2C C8C 110.9(7) . . ?
O3C C9C O2C 124.4(11) . . ?
O3C C9C O4C 123.7(11) . . ?
O2C C9C O4C 110.7(7) . . ?
C9C O4C C10C 109.7(6) . . ?
O4C C10C C8C 103.0(6) . . ?
O4C C10C H10C 111.2 . . ?
C8C C10C H10C 111.2 . . ?
O4C C10C H10D 111.2 . . ?
C8C C10C H10D 111.2 . . ?
H10C C10C H10D 109.1 . . ?
O1B C1B C2B 123.9(3) . . ?
O1B C1B C6B 115.3(3) . . ?
C2B C1B C6B 120.8(3) . . ?
C1B C2B C3B 118.6(3) . . ?
C1B C2B H2B 120.7 . . ?
C3B C2B H2B 120.7 . . ?
C4B C3B C2B 121.2(3) . . ?
C4B C3B H3B 119.4 . . ?
C2B C3B H3B 119.4 . . ?
C3B C4B C5B 119.4(3) . . ?
C3B C4B H4B 120.3 . . ?
C5B C4B H4B 120.3 . . ?
C6B C5B C4B 120.5(3) . . ?
C6B C5B H5B 119.7 . . ?
C4B C5B H5B 119.7 . . ?
C5B C6B C1B 119.5(3) . . ?
C5B C6B H6B 120.3 . . ?
C1B C6B H6B 120.3 . . ?
C1B O1B C7B 117.5(3) . . ?
O1B C7B C8B 107.4(2) . . ?
O1B C7B H7B1 110.2 . . ?
C8B C7B H7B1 110.2 . . ?
O1B C7B H7B2 110.2 . . ?
C8B C7B H7B2 110.2 . . ?
H7B1 C7B H7B2 108.5 . . ?
O2B C8B C7B 109.2(3) . . ?
O2B C8B C10B 103.2(2) . . ?
C7B C8B C10B 113.1(3) . . ?
O2B C8B H8B 110.4 . . ?
C7B C8B H8B 110.4 . . ?
C10B C8B H8B 110.4 . . ?
C9B O2B C8B 110.6(3) . . ?
O3B C9B O2B 124.8(4) . . ?
O3B C9B O4B 123.7(4) . . ?
O2B C9B O4B 111.5(3) . . ?
C9B O4B C10B 109.9(2) . . ?
O4B C10B C8B 103.4(2) . . ?
O4B C10B H10E 111.1 . . ?
C8B C10B H10E 111.1 . . ?
O4B C10B H10F 111.1 . . ?
C8B C10B H10F 111.1 . . ?
H10E C10B H10F 109.0 . . ?
O1D C1D C2D 118.3(7) . . ?
O1D C1D C6D 120.8(7) . . ?
C2D C1D C6D 120.0 . . ?
C3D C2D C1D 120.0 . . ?
C3D C2D H2D 120.0 . . ?
C1D C2D H2D 120.0 . . ?
C2D C3D C4D 120.0 . . ?
C2D C3D H3D 120.0 . . ?
C4D C3D H3D 120.0 . . ?
C5D C4D C3D 120.0 . . ?
C5D C4D H4D 120.0 . . ?
C3D C4D H4D 120.0 . . ?
C4D C5D C6D 120.0 . . ?
C4D C5D H5D 120.0 . . ?
C6D C5D H5D 120.0 . . ?
C5D C6D C1D 120.0 . . ?
C5D C6D H6D 120.0 . . ?
C1D C6D H6D 120.0 . . ?
C1D O1D C7D 118.6(8) . . ?
O1D C7D C8D 107.1(8) . . ?
O1D C7D H7D1 110.3 . . ?
C8D C7D H7D1 110.3 . . ?
O1D C7D H7D2 110.3 . . ?
C8D C7D H7D2 110.3 . . ?
H7D1 C7D H7D2 108.6 . . ?
O2D C8D C7D 109.4(9) . . ?
O2D C8D C10D 103.1(6) . . ?
C7D C8D C10D 113.1(8) . . ?
O2D C8D H8D 110.3 . . ?
C7D C8D H8D 110.3 . . ?
C10D C8D H8D 110.3 . . ?
C9D O2D C8D 110.5(7) . . ?
O3D C9D O2D 124.3(10) . . ?
O3D C9D O4D 124.5(10) . . ?
O2D C9D O4D 110.8(7) . . ?
C9D O4D C10D 110.4(6) . . ?
O4D C10D C8D 103.5(5) . . ?
O4D C10D H10G 111.1 . . ?
C8D C10D H10G 111.1 . . ?
O4D C10D H10H 111.1 . . ?
C8D C10D H10H 111.1 . . ?
H10G C10D H10H 109.0 . . ?

_refine_diff_density_max         0.321
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.057

_shelxl_version_number           2013-2

