# Electronic Supplementary Material (ESI) 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_am_tkg1_auto
_database_code_depnum_ccdc_archive 'CCDC 2287904'
loop_
_audit_author_name
_audit_author_address
'Tridib K. Goswami' 'Gauhati University'
_audit_update_record             
;
2023-12-31 deposited with the CCDC.	2024-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C54 H32 Cu2 F2 N4 O6, 2(Cl O4)'
_chemical_formula_sum            'C54 H32 Cl2 Cu2 F2 N4 O14'
_chemical_formula_weight         1196.81

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'
F F 0.0171 0.0103 '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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   13.1620(3)
_cell_length_b                   26.0801(6)
_cell_length_c                   13.5797(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.001(2)
_cell_angle_gamma                90
_cell_volume                     4650.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    19544
_cell_measurement_theta_min      1.7920
_cell_measurement_theta_max      31.9880

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_F_000             2424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.118
_shelx_estimated_absorpt_T_min   0.824
_shelx_estimated_absorpt_T_max   0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.42543
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'SCALE3 ABSPACK'
_exptl_absorpt_special_details   
'Absorption correction using spherical harmonics'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45242
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.083
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             10112
_reflns_number_gt                8246
_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 1.171.42.88a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_structure_solution    'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.1088P)²+7.7278P] 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         10112
_refine_ls_number_parameters     703
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0655
_refine_ls_wR_factor_ref         0.1897
_refine_ls_wR_factor_gt          0.1810
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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
Cu1 Cu 0.33548(3) 0.10445(2) 0.52393(3) 0.02009(14) Uani 1 1 d . . . . .
Cu2 Cu 0.12998(3) 0.02991(2) 0.49348(3) 0.02070(14) Uani 1 1 d . . . . .
Cl1 Cl 0.77023(10) 0.06893(4) 0.12573(8) 0.0443(3) Uani 1 1 d . . . . .
Cl2 Cl 0.22176(12) 0.21084(5) 0.13532(9) 0.0564(4) Uani 1 1 d . . . . .
F1 F 0.4260(2) -0.20309(9) 0.6795(2) 0.0446(6) Uani 1 1 d . . . . .
F2 F 0.0490(2) 0.33678(9) 0.3383(2) 0.0501(7) Uani 1 1 d . . . . .
O1 O 0.3423(2) 0.03094(9) 0.52728(19) 0.0241(5) Uani 1 1 d . . . . .
O2 O 0.35852(19) 0.09832(9) 0.38515(18) 0.0220(5) Uani 1 1 d . . . . .
O3 O 0.41526(19) -0.05063(9) 0.32772(19) 0.0253(5) Uani 1 1 d . . . . .
O4 O 0.1274(2) 0.10336(9) 0.49259(19) 0.0252(5) Uani 1 1 d . . . . .
O5 O 0.10326(19) 0.03550(9) 0.63173(19) 0.0243(5) Uani 1 1 d . . . . .
O6 O 0.05523(19) 0.18520(10) 0.6921(2) 0.0277(6) Uani 1 1 d . . . . .
O7 O 0.7118(5) 0.03173(17) 0.1710(4) 0.104(2) Uani 1 1 d . . . . .
O8 O 0.7098(4) 0.09797(15) 0.0539(4) 0.0837(16) Uani 1 1 d . . . . .
O9 O 0.8478(5) 0.0437(2) 0.0768(3) 0.0996(19) Uani 1 1 d . . . . .
O10 O 0.8159(4) 0.10199(14) 0.1996(3) 0.0685(13) Uani 1 1 d . . . . .
O11 O 0.2198(9) 0.1646(2) 0.1569(9) 0.244(7) Uani 1 1 d . . . . .
O12 O 0.2365(5) 0.2305(2) 0.0411(4) 0.1014(19) Uani 1 1 d . . . . .
O13 O 0.2729(5) 0.24137(17) 0.2093(3) 0.0822(15) Uani 1 1 d . . . . .
O14 O 0.1043(4) 0.2219(2) 0.1282(4) 0.1023(18) Uani 1 1 d . . . . .
N1 N 0.3284(2) 0.17970(11) 0.5219(2) 0.0211(6) Uani 1 1 d . . . . .
N2 N 0.3299(2) 0.11313(11) 0.6683(2) 0.0209(6) Uani 1 1 d . . . . .
N3 N 0.1384(2) 0.02328(11) 0.3489(2) 0.0225(6) Uani 1 1 d . . . . .
N4 N 0.1363(2) -0.04580(11) 0.4910(2) 0.0205(6) Uani 1 1 d . . . . .
C1 C 0.3270(3) 0.21121(14) 0.4460(3) 0.0248(7) Uani 1 1 d . . . . .
H1 H 0.331147 0.197372 0.381707 0.030 Uiso 1 1 calc R U . . .
C2 C 0.3197(3) 0.26458(14) 0.4571(3) 0.0274(8) Uani 1 1 d . . . . .
H2 H 0.320048 0.286388 0.401083 0.033 Uiso 1 1 calc R U . . .
C3 C 0.3121(3) 0.28504(14) 0.5496(3) 0.0295(8) Uani 1 1 d . . . . .
H3 H 0.306897 0.321094 0.557977 0.035 Uiso 1 1 calc R U . . .
C4 C 0.3119(3) 0.25200(14) 0.6323(3) 0.0250(7) Uani 1 1 d . . . . .
C5 C 0.2997(3) 0.26837(15) 0.7323(3) 0.0313(8) Uani 1 1 d . . . . .
H5 H 0.293105 0.303890 0.746018 0.038 Uiso 1 1 calc R U . . .
C6 C 0.2976(3) 0.23435(15) 0.8066(3) 0.0311(8) Uani 1 1 d . . . . .
H6 H 0.288519 0.246321 0.871453 0.037 Uiso 1 1 calc R U . . .
C7 C 0.3088(3) 0.18013(14) 0.7900(3) 0.0245(7) Uani 1 1 d . . . . .
C8 C 0.3064(3) 0.14200(15) 0.8635(3) 0.0277(8) Uani 1 1 d . . . . .
H8 H 0.298180 0.151237 0.930161 0.033 Uiso 1 1 calc R U . . .
C9 C 0.3161(3) 0.09154(15) 0.8379(3) 0.0265(7) Uani 1 1 d . . . . .
H9 H 0.314958 0.065591 0.886853 0.032 Uiso 1 1 calc R U . . .
C10 C 0.3277(3) 0.07813(14) 0.7387(3) 0.0248(7) Uani 1 1 d . . . . .
H10 H 0.334112 0.042964 0.721934 0.030 Uiso 1 1 calc R U . . .
C11 C 0.3211(2) 0.16380(13) 0.6932(3) 0.0211(7) Uani 1 1 d . . . . .
C12 C 0.3215(2) 0.19987(13) 0.6141(3) 0.0210(7) Uani 1 1 d . . . . .
C13 C 0.1358(3) 0.05892(14) 0.2808(3) 0.0268(7) Uani 1 1 d . . . . .
H13 H 0.125001 0.093477 0.299585 0.032 Uiso 1 1 calc R U . . .
C14 C 0.1485(3) 0.04787(15) 0.1806(3) 0.0290(8) Uani 1 1 d . . . . .
H14 H 0.145101 0.074439 0.132644 0.035 Uiso 1 1 calc R U . . .
C15 C 0.1660(3) -0.00193(16) 0.1538(3) 0.0293(8) Uani 1 1 d . . . . .
H15 H 0.175239 -0.009950 0.086737 0.035 Uiso 1 1 calc R U . . .
C16 C 0.1701(3) -0.04134(14) 0.2255(3) 0.0243(7) Uani 1 1 d . . . . .
C17 C 0.1901(3) -0.09397(15) 0.2069(3) 0.0290(8) Uani 1 1 d . . . . .
H17 H 0.203178 -0.104459 0.142014 0.035 Uiso 1 1 calc R U . . .
C18 C 0.1909(3) -0.12946(14) 0.2799(3) 0.0275(8) Uani 1 1 d . . . . .
H18 H 0.205199 -0.164235 0.265345 0.033 Uiso 1 1 calc R U . . .
C19 C 0.1706(3) -0.11545(14) 0.3790(3) 0.0244(7) Uani 1 1 d . . . . .
C20 C 0.1676(3) -0.15011(14) 0.4584(3) 0.0266(8) Uani 1 1 d . . . . .
H20 H 0.178867 -0.185679 0.448711 0.032 Uiso 1 1 calc R U . . .
C21 C 0.1481(3) -0.13168(14) 0.5505(3) 0.0280(8) Uani 1 1 d . . . . .
H21 H 0.144544 -0.154735 0.604270 0.034 Uiso 1 1 calc R U . . .
C22 C 0.1335(3) -0.07913(14) 0.5647(3) 0.0237(7) Uani 1 1 d . . . . .
H22 H 0.121340 -0.066986 0.628814 0.028 Uiso 1 1 calc R U . . .
C23 C 0.1534(2) -0.06348(13) 0.3989(3) 0.0205(7) Uani 1 1 d . . . . .
C24 C 0.1531(3) -0.02642(13) 0.3223(3) 0.0216(7) Uani 1 1 d . . . . .
C25 C 0.4163(3) -0.16237(15) 0.6160(3) 0.0328(9) Uani 1 1 d . . . . .
C26 C 0.3949(3) -0.11511(15) 0.6545(3) 0.0306(8) Uani 1 1 d . . . . .
H26 H 0.386306 -0.110962 0.722954 0.037 Uiso 1 1 calc R U . . .
C27 C 0.3864(3) -0.07361(14) 0.5902(3) 0.0254(7) Uani 1 1 d . . . . .
H27 H 0.370568 -0.040644 0.614623 0.031 Uiso 1 1 calc R U . . .
C28 C 0.4011(3) -0.07996(13) 0.4893(3) 0.0236(7) Uani 1 1 d . . . . .
C29 C 0.4208(3) -0.12919(14) 0.4538(3) 0.0284(8) Uani 1 1 d . . . . .
H29 H 0.429565 -0.134110 0.385563 0.034 Uiso 1 1 calc R U . . .
C30 C 0.4274(3) -0.17070(14) 0.5175(3) 0.0333(9) Uani 1 1 d . . . . .
H30 H 0.439420 -0.204227 0.493580 0.040 Uiso 1 1 calc R U . . .
C31 C 0.3952(3) -0.03641(13) 0.4207(3) 0.0226(7) Uani 1 1 d . . . . .
C32 C 0.4122(3) -0.01657(14) 0.2519(3) 0.0250(7) Uani 1 1 d . . . . .
C33 C 0.4192(3) -0.03651(16) 0.1575(3) 0.0310(8) Uani 1 1 d . . . . .
H33 H 0.426880 -0.072290 0.147264 0.037 Uiso 1 1 calc R U . . .
C34 C 0.4147(3) -0.00249(17) 0.0792(3) 0.0346(9) Uani 1 1 d . . . . .
H34 H 0.417475 -0.015430 0.014069 0.042 Uiso 1 1 calc R U . . .
C35 C 0.4062(3) 0.05023(17) 0.0932(3) 0.0347(9) Uani 1 1 d . . . . .
H35 H 0.406660 0.072776 0.038263 0.042 Uiso 1 1 calc R U . . .
C36 C 0.3971(3) 0.06978(15) 0.1866(3) 0.0279(8) Uani 1 1 d . . . . .
H36 H 0.390424 0.105663 0.196383 0.033 Uiso 1 1 calc R U . . .
C37 C 0.3978(3) 0.03577(14) 0.2674(3) 0.0238(7) Uani 1 1 d . . . . .
C38 C 0.3764(2) 0.05191(13) 0.3646(3) 0.0208(7) Uani 1 1 d . . . . .
C39 C 0.3710(2) 0.01399(13) 0.4412(3) 0.0203(7) Uani 1 1 d . . . . .
C40 C 0.0539(3) 0.29650(16) 0.4026(4) 0.0384(10) Uani 1 1 d . . . . .
C41 C 0.0450(3) 0.30519(16) 0.5002(4) 0.0424(11) Uani 1 1 d . . . . .
H41 H 0.034360 0.338968 0.523564 0.051 Uiso 1 1 calc R U . . .
C42 C 0.0517(3) 0.26434(15) 0.5652(4) 0.0373(9) Uani 1 1 d . . . . .
H42 H 0.045148 0.269899 0.633620 0.045 Uiso 1 1 calc R U . . .
C43 C 0.0681(3) 0.21434(14) 0.5297(3) 0.0263(8) Uani 1 1 d . . . . .
C44 C 0.0758(3) 0.20706(15) 0.4290(3) 0.0311(8) Uani 1 1 d . . . . .
H44 H 0.086500 0.173534 0.404413 0.037 Uiso 1 1 calc R U . . .
C45 C 0.0682(3) 0.24830(16) 0.3639(3) 0.0345(9) Uani 1 1 d . . . . .
H45 H 0.072588 0.243428 0.295028 0.041 Uiso 1 1 calc R U . . .
C46 C 0.0756(3) 0.17079(14) 0.5990(3) 0.0250(7) Uani 1 1 d . . . . .
C47 C 0.0990(2) 0.12055(13) 0.5790(3) 0.0217(7) Uani 1 1 d . . . . .
C48 C 0.0908(3) 0.08233(14) 0.6544(3) 0.0229(7) Uani 1 1 d . . . . .
C49 C 0.0701(3) 0.09888(14) 0.7518(3) 0.0241(7) Uani 1 1 d . . . . .
C50 C 0.0666(3) 0.06456(15) 0.8325(3) 0.0273(8) Uani 1 1 d . . . . .
H50 H 0.076123 0.028829 0.823244 0.033 Uiso 1 1 calc R U . . .
C51 C 0.0493(3) 0.08342(17) 0.9240(3) 0.0349(9) Uani 1 1 d . . . . .
H51 H 0.045406 0.060586 0.978097 0.042 Uiso 1 1 calc R U . . .
C52 C 0.0371(3) 0.13638(18) 0.9382(3) 0.0371(9) Uani 1 1 d . . . . .
H52 H 0.026699 0.149004 1.002320 0.044 Uiso 1 1 calc R U . . .
C53 C 0.0402(3) 0.17028(16) 0.8607(3) 0.0340(9) Uani 1 1 d . . . . .
H53 H 0.032047 0.206063 0.870677 0.041 Uiso 1 1 calc R U . . .
C54 C 0.0555(3) 0.15077(15) 0.7673(3) 0.0273(8) Uani 1 1 d . . . . .


_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
Cu1 O1 1.920(2) . ?
Cu1 O2 1.936(2) . ?
Cu1 N1 1.965(3) . ?
Cu1 N2 1.979(3) . ?
Cu2 O4 1.916(2) . ?
Cu2 O5 1.940(3) . ?
Cu2 N4 1.977(3) . ?
Cu2 N3 1.982(3) . ?
Cl1 O7 1.406(5) . ?
Cl1 O9 1.419(5) . ?
Cl1 O10 1.424(4) . ?
Cl1 O8 1.432(4) . ?
Cl2 O11 1.242(6) . ?
Cl2 O12 1.403(5) . ?
Cl2 O13 1.414(4) . ?
Cl2 O14 1.569(6) . ?
F1 C25 1.368(4) . ?
F2 C40 1.365(5) . ?
O1 C39 1.329(4) . ?
O2 C38 1.268(4) . ?
O3 C32 1.358(5) . ?
O3 C31 1.359(4) . ?
O4 C47 1.334(4) . ?
O5 C48 1.273(4) . ?
O6 C54 1.360(5) . ?
O6 C46 1.363(4) . ?
N1 C1 1.317(5) . ?
N1 C12 1.367(4) . ?
N2 C10 1.324(5) . ?
N2 C11 1.371(4) . ?
N3 C13 1.309(5) . ?
N3 C24 1.363(4) . ?
N4 C22 1.328(5) . ?
N4 C23 1.367(4) . ?
C1 C2 1.404(5) . ?
C2 C3 1.375(6) . ?
C3 C4 1.415(5) . ?
C4 C12 1.389(5) . ?
C4 C5 1.444(5) . ?
C5 C6 1.345(6) . ?
C6 C7 1.441(5) . ?
C7 C11 1.402(5) . ?
C7 C8 1.412(5) . ?
C8 C9 1.369(5) . ?
C9 C10 1.410(5) . ?
C11 C12 1.428(5) . ?
C13 C14 1.413(5) . ?
C14 C15 1.372(6) . ?
C15 C16 1.414(5) . ?
C16 C24 1.404(5) . ?
C16 C17 1.423(5) . ?
C17 C18 1.356(6) . ?
C18 C19 1.437(5) . ?
C19 C23 1.403(5) . ?
C19 C20 1.410(5) . ?
C20 C21 1.380(6) . ?
C21 C22 1.399(5) . ?
C23 C24 1.420(5) . ?
C25 C30 1.373(6) . ?
C25 C26 1.376(6) . ?
C26 C27 1.391(5) . ?
C27 C28 1.407(5) . ?
C28 C29 1.402(5) . ?
C28 C31 1.468(5) . ?
C29 C30 1.385(6) . ?
C31 C39 1.386(5) . ?
C32 C33 1.392(5) . ?
C32 C37 1.396(5) . ?
C33 C34 1.383(6) . ?
C34 C35 1.394(6) . ?
C35 C36 1.380(5) . ?
C36 C37 1.410(5) . ?
C37 C38 1.432(5) . ?
C38 C39 1.441(5) . ?
C40 C41 1.358(7) . ?
C40 C45 1.380(6) . ?
C41 C42 1.382(6) . ?
C42 C43 1.412(5) . ?
C43 C44 1.391(6) . ?
C43 C46 1.473(5) . ?
C44 C45 1.391(6) . ?
C46 C47 1.377(5) . ?
C47 C48 1.438(5) . ?
C48 C49 1.436(5) . ?
C49 C54 1.385(5) . ?
C49 C50 1.418(5) . ?
C50 C51 1.370(5) . ?
C51 C52 1.405(6) . ?
C52 C53 1.377(6) . ?
C53 C54 1.395(5) . ?

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 Cu1 O2 86.01(10) . . ?
O1 Cu1 N1 179.43(11) . . ?
O2 Cu1 N1 94.56(11) . . ?
O1 Cu1 N2 95.49(11) . . ?
O2 Cu1 N2 172.92(11) . . ?
N1 Cu1 N2 83.94(12) . . ?
O4 Cu2 O5 85.79(10) . . ?
O4 Cu2 N4 178.01(11) . . ?
O5 Cu2 N4 95.86(11) . . ?
O4 Cu2 N3 94.78(11) . . ?
O5 Cu2 N3 172.74(11) . . ?
N4 Cu2 N3 83.73(12) . . ?
O7 Cl1 O9 108.6(4) . . ?
O7 Cl1 O10 109.1(3) . . ?
O9 Cl1 O10 109.2(4) . . ?
O7 Cl1 O8 111.6(4) . . ?
O9 Cl1 O8 108.0(3) . . ?
O10 Cl1 O8 110.3(3) . . ?
O11 Cl2 O12 125.1(7) . . ?
O11 Cl2 O13 113.3(5) . . ?
O12 Cl2 O13 110.7(3) . . ?
O11 Cl2 O14 98.9(6) . . ?
O12 Cl2 O14 94.3(4) . . ?
O13 Cl2 O14 111.0(3) . . ?
C39 O1 Cu1 109.1(2) . . ?
C38 O2 Cu1 109.7(2) . . ?
C32 O3 C31 121.9(3) . . ?
C47 O4 Cu2 109.7(2) . . ?
C48 O5 Cu2 110.0(2) . . ?
C54 O6 C46 121.6(3) . . ?
C1 N1 C12 118.6(3) . . ?
C1 N1 Cu1 129.2(2) . . ?
C12 N1 Cu1 112.2(2) . . ?
C10 N2 C11 118.7(3) . . ?
C10 N2 Cu1 129.8(2) . . ?
C11 N2 Cu1 111.4(2) . . ?
C13 N3 C24 119.0(3) . . ?
C13 N3 Cu2 129.5(3) . . ?
C24 N3 Cu2 111.4(2) . . ?
C22 N4 C23 119.0(3) . . ?
C22 N4 Cu2 129.6(2) . . ?
C23 N4 Cu2 111.2(2) . . ?
N1 C1 C2 122.1(3) . . ?
C3 C2 C1 119.5(4) . . ?
C2 C3 C4 119.5(3) . . ?
C12 C4 C3 116.7(3) . . ?
C12 C4 C5 118.3(3) . . ?
C3 C4 C5 124.9(3) . . ?
C6 C5 C4 121.3(3) . . ?
C5 C6 C7 121.5(4) . . ?
C11 C7 C8 117.3(3) . . ?
C11 C7 C6 117.7(3) . . ?
C8 C7 C6 125.0(3) . . ?
C9 C8 C7 119.3(3) . . ?
C8 C9 C10 120.0(3) . . ?
N2 C10 C9 121.9(3) . . ?
N2 C11 C7 122.8(3) . . ?
N2 C11 C12 116.4(3) . . ?
C7 C11 C12 120.8(3) . . ?
N1 C12 C4 123.5(3) . . ?
N1 C12 C11 116.0(3) . . ?
C4 C12 C11 120.4(3) . . ?
N3 C13 C14 122.4(3) . . ?
C15 C14 C13 118.8(4) . . ?
C14 C15 C16 120.3(4) . . ?
C24 C16 C15 116.3(3) . . ?
C24 C16 C17 118.4(3) . . ?
C15 C16 C17 125.3(3) . . ?
C18 C17 C16 121.4(3) . . ?
C17 C18 C19 121.2(3) . . ?
C23 C19 C20 117.3(3) . . ?
C23 C19 C18 117.9(3) . . ?
C20 C19 C18 124.8(3) . . ?
C21 C20 C19 119.1(3) . . ?
C20 C21 C22 120.2(3) . . ?
N4 C22 C21 121.7(3) . . ?
N4 C23 C19 122.7(3) . . ?
N4 C23 C24 116.7(3) . . ?
C19 C23 C24 120.6(3) . . ?
N3 C24 C16 123.1(3) . . ?
N3 C24 C23 116.5(3) . . ?
C16 C24 C23 120.3(3) . . ?
F1 C25 C30 118.7(4) . . ?
F1 C25 C26 117.9(4) . . ?
C30 C25 C26 123.4(4) . . ?
C25 C26 C27 117.9(4) . . ?
C26 C27 C28 120.7(3) . . ?
C29 C28 C27 119.0(3) . . ?
C29 C28 C31 119.5(3) . . ?
C27 C28 C31 121.5(3) . . ?
C30 C29 C28 120.4(4) . . ?
C25 C30 C29 118.6(4) . . ?
O3 C31 C39 120.5(3) . . ?
O3 C31 C28 111.9(3) . . ?
C39 C31 C28 127.5(3) . . ?
O3 C32 C33 116.9(3) . . ?
O3 C32 C37 121.5(3) . . ?
C33 C32 C37 121.5(4) . . ?
C34 C33 C32 117.8(4) . . ?
C33 C34 C35 121.9(4) . . ?
C36 C35 C34 120.2(4) . . ?
C35 C36 C37 119.1(4) . . ?
C32 C37 C36 119.5(3) . . ?
C32 C37 C38 117.6(3) . . ?
C36 C37 C38 122.7(3) . . ?
O2 C38 C37 122.4(3) . . ?
O2 C38 C39 118.5(3) . . ?
C37 C38 C39 119.1(3) . . ?
O1 C39 C31 125.2(3) . . ?
O1 C39 C38 116.0(3) . . ?
C31 C39 C38 118.8(3) . . ?
C41 C40 F2 119.5(4) . . ?
C41 C40 C45 123.1(4) . . ?
F2 C40 C45 117.4(4) . . ?
C40 C41 C42 119.3(4) . . ?
C41 C42 C43 119.9(4) . . ?
C44 C43 C42 119.0(4) . . ?
C44 C43 C46 121.1(3) . . ?
C42 C43 C46 119.9(4) . . ?
C45 C44 C43 120.8(4) . . ?
C40 C45 C44 117.9(4) . . ?
O6 C46 C47 120.4(3) . . ?
O6 C46 C43 111.8(3) . . ?
C47 C46 C43 127.9(3) . . ?
O4 C47 C46 125.0(3) . . ?
O4 C47 C48 115.7(3) . . ?
C46 C47 C48 119.4(3) . . ?
O5 C48 C49 123.2(3) . . ?
O5 C48 C47 118.4(3) . . ?
C49 C48 C47 118.4(3) . . ?
C54 C49 C50 119.2(3) . . ?
C54 C49 C48 118.1(3) . . ?
C50 C49 C48 122.7(3) . . ?
C51 C50 C49 119.4(4) . . ?
C50 C51 C52 120.3(4) . . ?
C53 C52 C51 121.1(4) . . ?
C52 C53 C54 118.3(4) . . ?
O6 C54 C49 121.7(3) . . ?
O6 C54 C53 116.7(3) . . ?
C49 C54 C53 121.6(4) . . ?

_refine_diff_density_max         2.592
_refine_diff_density_min         -1.073
_refine_diff_density_rms         0.134

####################################################################### 
# 
# 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_tkg_cn_tpp_0m
_database_code_depnum_ccdc_archive 'CCDC 2287905'
loop_
_audit_author_name
_audit_author_address
'Tridib K. Goswami'
;Gauhati University
India
;
_audit_update_record             
;
2024-01-06 deposited with the CCDC.	2024-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 O3'
_chemical_formula_sum            'C15 H10 O3'
_chemical_formula_weight         238.23

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

_cell_length_a                   5.4597(5)
_cell_length_b                   11.4059(12)
_cell_length_c                   18.1880(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1132.62(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2903
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      28.02

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5117
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.744
_diffrn_reflns_theta_max         29.026
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             2871
_reflns_number_gt                2390
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_max     0.926
_reflns_Friedel_fraction_full    0.976

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0432P)²+0.0366P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.124(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 823 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   2.1(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2871
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0923
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
C1 C 0.2050(3) 0.07619(15) 0.89585(10) 0.0415(4) Uani 1 1 d . . . . .
C2 C 0.0474(4) 0.17177(17) 0.89397(13) 0.0524(5) Uani 1 1 d . . . . .
H2 H 0.063606 0.228965 0.857848 0.063 Uiso 1 1 calc R U . . .
C3 C -0.1322(4) 0.18025(19) 0.94630(14) 0.0595(6) Uani 1 1 d . . . . .
H3 H -0.238549 0.243929 0.945685 0.071 Uiso 1 1 calc R U . . .
C4 C -0.1573(4) 0.09500(18) 1.00020(13) 0.0559(5) Uani 1 1 d . . . . .
H4 H -0.280239 0.101804 1.035346 0.067 Uiso 1 1 calc R U . . .
C5 C -0.0019(3) 0.00102(17) 1.00180(10) 0.0472(4) Uani 1 1 d . . . . .
H5 H -0.020567 -0.056304 1.037731 0.057 Uiso 1 1 calc R U . . .
C6 C 0.1867(3) -0.00932(15) 0.94912(9) 0.0391(4) Uani 1 1 d . . . . .
C7 C 0.3571(3) -0.10618(15) 0.94846(9) 0.0372(4) Uani 1 1 d . . . . .
C8 C 0.5322(3) -0.10669(15) 0.88830(9) 0.0368(4) Uani 1 1 d . . . . .
C9 C 0.5386(3) -0.01937(14) 0.83758(9) 0.0374(4) Uani 1 1 d . . . . .
C10 C 0.7090(4) -0.00504(16) 0.77513(9) 0.0411(4) Uani 1 1 d . . . . .
C11 C 0.9057(4) -0.07968(18) 0.76394(11) 0.0473(5) Uani 1 1 d . . . . .
H11 H 0.929015 -0.143732 0.794803 0.057 Uiso 1 1 calc R U . . .
C12 C 1.0683(4) -0.0588(2) 0.70659(12) 0.0567(6) Uani 1 1 d . . . . .
H12 H 1.201270 -0.108616 0.699689 0.068 Uiso 1 1 calc R U . . .
C13 C 1.0347(5) 0.0343(2) 0.66017(12) 0.0624(6) Uani 1 1 d . . . . .
H13 H 1.145403 0.047873 0.622257 0.075 Uiso 1 1 calc R U . . .
C14 C 0.8374(5) 0.1077(2) 0.66955(12) 0.0631(6) Uani 1 1 d . . . . .
H14 H 0.812983 0.169887 0.637311 0.076 Uiso 1 1 calc R U . . .
C15 C 0.6754(4) 0.08934(18) 0.72664(11) 0.0525(5) Uani 1 1 d . . . . .
H15 H 0.543285 0.139781 0.733030 0.063 Uiso 1 1 calc R U . . .
O1 O 0.3776(2) 0.07177(11) 0.84178(7) 0.0445(3) Uani 1 1 d . . . . .
O2 O 0.3644(2) -0.18477(11) 0.99485(7) 0.0510(4) Uani 1 1 d . . . . .
O3 O 0.6890(3) -0.19773(12) 0.88573(8) 0.0504(4) Uani 1 1 d . . . . .
H3A H 0.695(5) -0.2333(19) 0.9283(15) 0.068(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.363(2) . ?
C1 C6 1.378(2) . ?
C1 C2 1.389(3) . ?
C2 C3 1.370(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.411(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.444(2) . ?
C7 O2 1.232(2) . ?
C7 C8 1.453(2) . ?
C8 O3 1.347(2) . ?
C8 C9 1.358(2) . ?
C9 O1 1.364(2) . ?
C9 C10 1.477(3) . ?
C10 C11 1.386(3) . ?
C10 C15 1.404(3) . ?
C11 C12 1.390(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
O3 H3A 0.88(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C6 122.09(16) . . ?
O1 C1 C2 116.06(17) . . ?
C6 C1 C2 121.84(18) . . ?
C3 C2 C1 118.8(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 120.8(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.24(18) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.11(17) . . ?
C1 C6 C7 119.24(16) . . ?
C5 C6 C7 122.64(16) . . ?
O2 C7 C6 124.87(16) . . ?
O2 C7 C8 119.45(16) . . ?
C6 C7 C8 115.67(14) . . ?
O3 C8 C9 121.70(16) . . ?
O3 C8 C7 116.59(15) . . ?
C9 C8 C7 121.71(16) . . ?
C8 C9 O1 120.29(16) . . ?
C8 C9 C10 128.30(16) . . ?
O1 C9 C10 111.39(14) . . ?
C11 C10 C15 118.71(18) . . ?
C11 C10 C9 122.21(16) . . ?
C15 C10 C9 119.05(18) . . ?
C10 C11 C12 120.00(19) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C15 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 120.4(2) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C1 O1 C9 120.95(14) . . ?
C8 O3 H3A 110.6(16) . . ?

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_MONO_a
_database_code_depnum_ccdc_archive 'CCDC 2287906'
loop_
_audit_author_name
_audit_author_address
'Tridib K. Goswami'
;Gauhati University
India
;
_audit_update_record             
;
2024-01-06 deposited with the CCDC.	2024-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H8 F2 O3'
_chemical_formula_sum            'C15 H8 F2 O3'
_chemical_formula_weight         274.21

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.7113(18)
_cell_length_b                   15.507(2)
_cell_length_c                   7.1679(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.00
_cell_angle_gamma                90
_cell_volume                     1190.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3166
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      28.71

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   Sheldrick,G.M.,(2003)
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5402
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.131
_diffrn_reflns_theta_max         29.198
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3028
_reflns_number_gt                2193
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1108P)²] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.220(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3028
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.1771
_refine_ls_wR_factor_gt          0.1613
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
F1 F 0.60902(12) 0.24764(9) 0.6984(3) 0.0955(5) Uani 1 1 d . . . . .
F2 F 0.60620(12) 0.54809(8) 0.7113(2) 0.0783(4) Uani 1 1 d . . . . .
O1 O 1.04998(9) 0.45245(8) 0.81072(15) 0.0450(3) Uani 1 1 d . . . . .
O2 O 0.76998(9) 0.36287(7) 0.48498(14) 0.0439(3) Uani 1 1 d . . . . .
O3 O 0.80852(11) 0.46140(8) 0.93501(15) 0.0476(3) Uani 1 1 d . . . . .
H3 H 0.867(3) 0.4812(16) 0.984(4) 0.085(8) Uiso 1 1 d . . . . .
C1 C 0.98862(13) 0.38886(8) 0.52468(19) 0.0337(3) Uani 1 1 d . . . . .
C2 C 0.88931(13) 0.35897(9) 0.4212(2) 0.0364(3) Uani 1 1 d . . . . .
C3 C 0.90630(16) 0.32297(11) 0.2445(2) 0.0454(4) Uani 1 1 d . . . . .
H3A H 0.838223 0.302082 0.176066 0.055 Uiso 1 1 calc R U . . .
C4 C 1.02461(16) 0.31867(10) 0.1726(2) 0.0465(4) Uani 1 1 d . . . . .
H4 H 1.035977 0.295548 0.054376 0.056 Uiso 1 1 calc R U . . .
C5 C 1.12592(15) 0.34824(10) 0.2739(2) 0.0455(4) Uani 1 1 d . . . . .
H5 H 1.205608 0.344933 0.224876 0.055 Uiso 1 1 calc R U . . .
C6 C 1.10864(13) 0.38273(10) 0.4481(2) 0.0400(4) Uani 1 1 d . . . . .
H6 H 1.177379 0.402398 0.516819 0.048 Uiso 1 1 calc R U . . .
C7 C 0.96672(12) 0.42531(9) 0.70914(19) 0.0339(3) Uani 1 1 d . . . . .
C8 C 0.83732(12) 0.42840(10) 0.76677(19) 0.0371(3) Uani 1 1 d . . . . .
C9 C 0.74673(13) 0.39823(10) 0.6566(2) 0.0399(4) Uani 1 1 d . . . . .
C10 C 0.61331(13) 0.39785(12) 0.7047(2) 0.0477(4) Uani 1 1 d . . . . .
C11 C 0.54674(16) 0.47330(14) 0.7349(2) 0.0565(5) Uani 1 1 d . . . . .
C12 C 0.42336(17) 0.47394(19) 0.7862(3) 0.0718(7) Uani 1 1 d . . . . .
H12 H 0.381498 0.525747 0.804104 0.086 Uiso 1 1 calc R U . . .
C13 C 0.36397(18) 0.3972(2) 0.8100(3) 0.0805(8) Uani 1 1 d . . . . .
H13 H 0.281304 0.396853 0.847542 0.097 Uiso 1 1 calc R U . . .
C14 C 0.42381(19) 0.3206(2) 0.7796(3) 0.0826(8) Uani 1 1 d . . . . .
H14 H 0.382237 0.268410 0.793957 0.099 Uiso 1 1 calc R U . . .
C15 C 0.54785(17) 0.32250(15) 0.7270(3) 0.0651(6) Uani 1 1 d . . . . .


_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
F1 C15 1.350(3) . ?
F2 C11 1.335(2) . ?
O1 C7 1.2165(17) . ?
O2 C2 1.3663(17) . ?
O2 C9 1.3736(18) . ?
O3 C8 1.3507(17) . ?
O3 H3 0.77(3) . ?
C1 C2 1.367(2) . ?
C1 C6 1.4097(19) . ?
C1 C7 1.4607(19) . ?
C2 C3 1.399(2) . ?
C3 C4 1.378(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.374(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.4540(18) . ?
C8 C9 1.326(2) . ?
C9 C10 1.4760(19) . ?
C10 C15 1.373(3) . ?
C10 C11 1.389(3) . ?
C11 C12 1.378(3) . ?
C12 C13 1.361(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.388(3) . ?
C14 H14 0.9300 . ?

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
C2 O2 C9 120.18(11) . . ?
C8 O3 H3 111.0(19) . . ?
C2 C1 C6 118.17(13) . . ?
C2 C1 C7 119.12(12) . . ?
C6 C1 C7 122.71(13) . . ?
O2 C2 C1 121.80(13) . . ?
O2 C2 C3 117.26(13) . . ?
C1 C2 C3 120.95(14) . . ?
C4 C3 C2 119.54(15) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C5 C4 C3 120.61(14) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.50(14) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 121.21(14) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
O1 C7 C8 120.74(12) . . ?
O1 C7 C1 123.23(12) . . ?
C8 C7 C1 116.03(12) . . ?
C9 C8 O3 119.30(12) . . ?
C9 C8 C7 120.71(13) . . ?
O3 C8 C7 119.99(12) . . ?
C8 C9 O2 122.15(12) . . ?
C8 C9 C10 124.32(13) . . ?
O2 C9 C10 113.52(12) . . ?
C15 C10 C11 115.71(16) . . ?
C15 C10 C9 121.94(16) . . ?
C11 C10 C9 122.33(16) . . ?
F2 C11 C12 119.29(19) . . ?
F2 C11 C10 117.68(15) . . ?
C12 C11 C10 123.0(2) . . ?
C13 C12 C11 118.7(2) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C14 121.17(18) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C13 C14 C15 118.5(2) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
F1 C15 C10 117.62(15) . . ?
F1 C15 C14 119.5(2) . . ?
C10 C15 C14 122.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O2 C2 C1 0.6(2) . . . . ?
C9 O2 C2 C3 -179.37(13) . . . . ?
C6 C1 C2 O2 -179.73(13) . . . . ?
C7 C1 C2 O2 0.5(2) . . . . ?
C6 C1 C2 C3 0.3(2) . . . . ?
C7 C1 C2 C3 -179.50(13) . . . . ?
O2 C2 C3 C4 179.06(14) . . . . ?
C1 C2 C3 C4 -0.9(2) . . . . ?
C2 C3 C4 C5 0.9(2) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
C7 C1 C6 C5 -179.85(13) . . . . ?
C2 C1 C7 O1 179.21(14) . . . . ?
C6 C1 C7 O1 -0.5(2) . . . . ?
C2 C1 C7 C8 -1.27(19) . . . . ?
C6 C1 C7 C8 178.99(13) . . . . ?
O1 C7 C8 C9 -179.49(15) . . . . ?
C1 C7 C8 C9 1.0(2) . . . . ?
O1 C7 C8 O3 -0.2(2) . . . . ?
C1 C7 C8 O3 -179.76(13) . . . . ?
O3 C8 C9 O2 -179.16(13) . . . . ?
C7 C8 C9 O2 0.1(2) . . . . ?
O3 C8 C9 C10 0.0(2) . . . . ?
C7 C8 C9 C10 179.25(14) . . . . ?
C2 O2 C9 C8 -1.0(2) . . . . ?
C2 O2 C9 C10 179.83(13) . . . . ?
C8 C9 C10 C15 -115.6(2) . . . . ?
O2 C9 C10 C15 63.6(2) . . . . ?
C8 C9 C10 C11 62.8(2) . . . . ?
O2 C9 C10 C11 -118.02(17) . . . . ?
C15 C10 C11 F2 -178.76(17) . . . . ?
C9 C10 C11 F2 2.8(2) . . . . ?
C15 C10 C11 C12 0.7(3) . . . . ?
C9 C10 C11 C12 -177.71(16) . . . . ?
F2 C11 C12 C13 -179.92(18) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C11 C12 C13 C14 -1.6(3) . . . . ?
C12 C13 C14 C15 1.2(4) . . . . ?
C11 C10 C15 F1 179.81(18) . . . . ?
C9 C10 C15 F1 -1.7(3) . . . . ?
C11 C10 C15 C14 -1.1(3) . . . . ?
C9 C10 C15 C14 177.31(18) . . . . ?
C13 C14 C15 F1 179.3(2) . . . . ?
C13 C14 C15 C10 0.2(3) . . . . ?

_refine_diff_density_max         0.440
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.110

