# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_2001gg02
_audit_block_doi                 10.5517/cc82gmd
_database_code_depnum_ccdc_archive 'CCDC 240703'
_audit_update_record             
;
2004-06-04 deposited with the CCDC.	2024-10-31 downloaded from the CCDC.
;

_audit_creation_date             2001-07-04T13:49:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C17 H14 N4 O4'
_chemical_formula_structural     'C17 H14 N4 O4'
_chemical_formula_sum            'C17 H14 N4 O4'
_chemical_formula_weight         338.32
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_Int_Tables_number      1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   8.615(3)
_cell_length_b                   9.5106(14)
_cell_length_c                   11.562(3)
_cell_angle_alpha                64.659(12)
_cell_angle_beta                 72.90(2)
_cell_angle_gamma                74.967(17)
_cell_volume                     808.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14
_cell_measurement_theta_min      15.64
_cell_measurement_theta_max      42.74
_cell_measurement_wavelength     1.54184

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

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.08
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_special_details           
;
?
;

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

_exptl_absorpt_coefficient_mu    0.852
_exptl_absorpt_factor_muR        0.066
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was   7
Theta correction was applied.
Weighted transmission curves were used.
No Fourier smoothing was applied.
;
_exptl_absorpt_correction_T_min  0.6039
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_correction_T_ave  0.7699

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

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      0.13358E-1
_diffrn_orient_matrix_ub_12      -0.111856
_diffrn_orient_matrix_ub_13      0.63306E-1
_diffrn_orient_matrix_ub_21      -0.8115E-2
_diffrn_orient_matrix_ub_22      0.36712E-1
_diffrn_orient_matrix_ub_23      0.71046E-1
_diffrn_orient_matrix_ub_31      -0.121901
_diffrn_orient_matrix_ub_32      0.3871E-2
_diffrn_orient_matrix_ub_33      0.22883E-1
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_standards_number         3
_diffrn_standards_interval_count 166
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        -3
_diffrn_standards_decay_corr_max 1.847
_diffrn_standards_decay_corr_min 0.949
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 1 4
1 3 0
3 1 2

_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_number            3483
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.33
_diffrn_reflns_theta_max         73.62
_diffrn_reflns_theta_full        73.62
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             3483
_reflns_number_gt                2042
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SIR97 (Altomare et al., 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1020P)²+1.1381P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3483
_refine_ls_number_parameters     451
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1515
_refine_ls_R_factor_gt           0.0776
_refine_ls_wR_factor_ref         0.301
_refine_ls_wR_factor_gt          0.2647
_refine_ls_goodness_of_fit_ref   1.254
_refine_ls_restrained_S_all      1.254
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(9)
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.068

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7649(13) 0.8600(14) -0.0807(11) 0.061(3) Uani 1 1 d . . .
C2 C 0.7354(15) 0.7356(14) -0.1163(11) 0.067(3) Uani 1 1 d . . .
H2 H 0.7711 0.626 -0.0623 0.08 Uiso 1 1 calc R . .
C3 C 0.5576(15) 0.7785(13) -0.1281(11) 0.061(3) Uani 1 1 d . . .
C4 C 0.419(2) 0.7146(18) -0.0545(14) 0.087(4) Uani 1 1 d . . .
H4 H 0.4231 0.6245 0.0214 0.105 Uiso 1 1 calc R . .
C5 C 0.271(2) 0.786(2) -0.094(2) 0.105(5) Uani 1 1 d . . .
H5 H 0.1762 0.7428 -0.0446 0.126 Uiso 1 1 calc R . .
C6 C 0.2639(19) 0.920(2) -0.208(2) 0.098(5) Uani 1 1 d . . .
H6 H 0.1644 0.966 -0.2341 0.118 Uiso 1 1 calc R . .
C7 C 0.4025(18) 0.9854(16) -0.2799(14) 0.079(4) Uani 1 1 d . . .
H7 H 0.3967 1.0779 -0.3538 0.095 Uiso 1 1 calc R . .
C8 C 0.5505(15) 0.9145(14) -0.2436(11) 0.064(3) Uani 1 1 d . . .
C9 C 0.7193(16) 0.9594(14) -0.2954(11) 0.068(3) Uani 1 1 d . . .
H9 H 0.7423 1.0306 -0.3876 0.082 Uiso 1 1 calc R . .
C10 C 0.7530(16) 1.0129(14) -0.1987(11) 0.069(3) Uani 1 1 d . . .
H10A H 0.8548 1.0563 -0.2324 0.083 Uiso 1 1 calc R . .
H10B H 0.6636 1.0905 -0.1782 0.083 Uiso 1 1 calc R . .
C11 C 0.8231(17) 0.7942(17) -0.2620(13) 0.082(4) Uani 1 1 d . . .
H11A H 0.9391 0.796 -0.2747 0.098 Uiso 1 1 calc R . .
H11B H 0.8077 0.7361 -0.3083 0.098 Uiso 1 1 calc R . .
N12 N 0.7980(12) 0.8289(11) 0.0283(9) 0.064(2) Uani 1 1 d . . .
N13 N 0.8176(12) 0.9587(12) 0.0453(9) 0.068(3) Uani 1 1 d . . .
H13 H 0.7917 1.0521 -0.0095 0.082 Uiso 1 1 calc R . .
C14 C 0.8777(14) 0.9379(14) 0.1488(11) 0.061(3) Uani 1 1 d . . .
C15 C 0.8900(14) 1.0602(14) 0.1798(11) 0.062(3) Uani 1 1 d . . .
C16 C 0.9616(14) 1.0325(14) 0.2835(10) 0.063(3) Uani 1 1 d . . .
H16 H 0.9704 1.1154 0.3025 0.076 Uiso 1 1 calc R . .
C17 C 1.0175(15) 0.8817(15) 0.3552(10) 0.062(3) Uani 1 1 d . . .
C18 C 1.0066(15) 0.7550(15) 0.3297(11) 0.070(3) Uani 1 1 d . . .
H18 H 1.0467 0.653 0.3809 0.084 Uiso 1 1 calc R . .
C19 C 0.9371(17) 0.7810(15) 0.2295(12) 0.073(3) Uani 1 1 d . . .
H19 H 0.928 0.6962 0.2132 0.088 Uiso 1 1 calc R . .
N20 N 0.8265(14) 1.2241(14) 0.1091(12) 0.078(3) Uani 1 1 d . . .
O21 O 0.7543(13) 1.2522(12) 0.0227(10) 0.093(3) Uani 1 1 d . . .
O22 O 0.8461(16) 1.3263(12) 0.1381(11) 0.108(4) Uani 1 1 d . . .
N23 N 1.0985(13) 0.8529(17) 0.4593(10) 0.076(3) Uani 1 1 d . . .
O24 O 1.1189(14) 0.9673(14) 0.4741(9) 0.097(3) Uani 1 1 d . . .
O25 O 1.1429(12) 0.7167(14) 0.5273(9) 0.094(3) Uani 1 1 d . . .
C51 C 0.5343(14) 0.6535(15) 0.4501(11) 0.064(3) Uani 1 1 d . . .
C52 C 0.5533(17) 0.4782(15) 0.4921(12) 0.073(3) Uani 1 1 d . . .
H52 H 0.5165 0.44 0.4397 0.087 Uiso 1 1 calc R . .
C53 C 0.7294(16) 0.4209(13) 0.5080(12) 0.068(3) Uani 1 1 d . . .
C54 C 0.868(2) 0.3602(17) 0.4392(16) 0.098(5) Uani 1 1 d . . .
H54 H 0.8642 0.3461 0.3654 0.118 Uiso 1 1 calc R . .
C55 C 1.014(2) 0.3205(19) 0.480(2) 0.117(7) Uani 1 1 d . . .
H55 H 1.1083 0.2776 0.4344 0.14 Uiso 1 1 calc R . .
C56 C 1.020(2) 0.3439(18) 0.588(2) 0.112(6) Uani 1 1 d . . .
H56 H 1.1192 0.3157 0.6149 0.135 Uiso 1 1 calc R . .
C57 C 0.8860(18) 0.4068(15) 0.6549(15) 0.083(4) Uani 1 1 d . . .
H57 H 0.8933 0.4259 0.7254 0.1 Uiso 1 1 calc R . .
C58 C 0.7382(15) 0.4426(13) 0.6184(12) 0.070(3) Uani 1 1 d . . .
C59 C 0.5697(16) 0.5157(15) 0.6670(11) 0.074(3) Uani 1 1 d . . .
H59 H 0.5468 0.5058 0.7582 0.088 Uiso 1 1 calc R . .
C60 C 0.5419(16) 0.6860(13) 0.5659(11) 0.067(3) Uani 1 1 d . . .
H60A H 0.44 0.7456 0.5956 0.081 Uiso 1 1 calc R . .
H60B H 0.6326 0.7413 0.5458 0.081 Uiso 1 1 calc R . .
C61 C 0.4615(17) 0.4356(16) 0.6379(13) 0.082(4) Uani 1 1 d . . .
H61A H 0.347 0.4838 0.6477 0.098 Uiso 1 1 calc R . .
H61B H 0.4714 0.323 0.6882 0.098 Uiso 1 1 calc R . .
N62 N 0.5108(12) 0.7505(12) 0.3381(9) 0.066(3) Uani 1 1 d . . .
N63 N 0.4933(12) 0.9082(12) 0.3175(9) 0.066(3) Uani 1 1 d . . .
H63 H 0.5258 0.935 0.3677 0.079 Uiso 1 1 calc R . .
C64 C 0.4246(13) 1.0193(14) 0.2175(10) 0.059(3) Uani 1 1 d . . .
C65 C 0.3885(15) 1.1806(15) 0.1948(11) 0.064(3) Uani 1 1 d . . .
C66 C 0.3065(15) 1.2902(15) 0.0975(12) 0.070(3) Uani 1 1 d . . .
H66 H 0.2792 1.3957 0.0865 0.084 Uiso 1 1 calc R . .
C67 C 0.2675(15) 1.2368(15) 0.0186(11) 0.068(3) Uani 1 1 d . . .
C68 C 0.3092(15) 1.0811(15) 0.0303(10) 0.067(3) Uani 1 1 d . . .
H68 H 0.2852 1.0492 -0.0274 0.081 Uiso 1 1 calc R . .
C69 C 0.3866(15) 0.9754(16) 0.1292(11) 0.067(3) Uani 1 1 d . . .
H69 H 0.415 0.8706 0.1378 0.081 Uiso 1 1 calc R . .
N70 N 0.4263(14) 1.2426(15) 0.2770(10) 0.081(3) Uani 1 1 d . . .
O71 O 0.4994(15) 1.1512(12) 0.3662(9) 0.097(3) Uani 1 1 d . . .
O72 O 0.3883(17) 1.3831(12) 0.2569(10) 0.111(4) Uani 1 1 d . . .
N73 N 0.1750(16) 1.3510(18) -0.0814(11) 0.090(4) Uani 1 1 d . . .
O74 O 0.1523(17) 1.4899(15) -0.0998(12) 0.122(4) Uani 1 1 d . . .
O75 O 0.1228(15) 1.2972(15) -0.1371(11) 0.115(4) Uani 1 1 d . . .



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

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N12 1.267(14) . ?
C1 C2 1.506(18) . ?
C1 C10 1.515(15) . ?
C2 C3 1.511(17) . ?
C2 C11 1.545(17) . ?
C2 H2 0.98 . ?
C3 C4 1.364(18) . ?
C3 C8 1.410(16) . ?
C4 C5 1.38(2) . ?
C4 H4 0.93 . ?
C5 C6 1.39(2) . ?
C5 H5 0.93 . ?
C6 C7 1.36(2) . ?
C6 H6 0.93 . ?
C7 C8 1.372(17) . ?
C7 H7 0.93 . ?
C8 C9 1.500(17) . ?
C9 C10 1.532(17) . ?
C9 C11 1.540(18) . ?
C9 H9 0.98 . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
N12 N13 1.388(13) . ?
N13 C14 1.359(14) . ?
N13 H13 0.86 . ?
C14 C15 1.392(17) . ?
C14 C19 1.432(16) . ?
C15 C16 1.402(16) . ?
C15 N20 1.459(15) . ?
C16 C17 1.355(16) . ?
C16 H16 0.93 . ?
C17 C18 1.387(16) . ?
C17 N23 1.458(15) . ?
C18 C19 1.359(16) . ?
C18 H18 0.93 . ?
C19 H19 0.93 . ?
N20 O22 1.218(15) . ?
N20 O21 1.228(14) . ?
N23 O25 1.221(14) . ?
N23 O24 1.233(15) . ?
C51 N62 1.266(14) . ?
C51 C52 1.502(17) . ?
C51 C60 1.520(16) . ?
C52 C53 1.511(18) . ?
C52 C61 1.558(19) . ?
C52 H52 0.98 . ?
C53 C54 1.369(19) . ?
C53 C58 1.403(17) . ?
C54 C55 1.37(2) . ?
C54 H54 0.93 . ?
C55 C56 1.38(3) . ?
C55 H55 0.93 . ?
C56 C57 1.34(2) . ?
C56 H56 0.93 . ?
C57 C58 1.373(17) . ?
C57 H57 0.93 . ?
C58 C59 1.495(17) . ?
C59 C61 1.529(18) . ?
C59 C60 1.546(16) . ?
C59 H59 0.98 . ?
C60 H60A 0.97 . ?
C60 H60B 0.97 . ?
C61 H61A 0.97 . ?
C61 H61B 0.97 . ?
N62 N63 1.388(12) . ?
N63 C64 1.355(14) . ?
N63 H63 0.86 . ?
C64 C69 1.399(16) . ?
C64 C65 1.405(17) . ?
C65 C66 1.390(16) . ?
C65 N70 1.455(16) . ?
C66 C67 1.366(18) . ?
C66 H66 0.93 . ?
C67 C68 1.387(18) . ?
C67 N73 1.473(15) . ?
C68 C69 1.371(16) . ?
C68 H68 0.93 . ?
C69 H69 0.93 . ?
N70 O72 1.225(14) . ?
N70 O71 1.244(14) . ?
N73 O75 1.204(16) . ?
N73 O74 1.216(18) . ?

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
N12 C1 C2 122.5(10) . . ?
N12 C1 C10 131.0(12) . . ?
C2 C1 C10 106.5(10) . . ?
C1 C2 C3 105.3(10) . . ?
C1 C2 C11 99.0(10) . . ?
C3 C2 C11 100.8(9) . . ?
C1 C2 H2 116.4 . . ?
C3 C2 H2 116.4 . . ?
C11 C2 H2 116.4 . . ?
C4 C3 C8 120.2(12) . . ?
C4 C3 C2 134.0(12) . . ?
C8 C3 C2 105.8(10) . . ?
C3 C4 C5 119.1(14) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C4 C5 C6 120.8(15) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 120.0(14) . . ?
C7 C6 H6 120 . . ?
C5 C6 H6 120 . . ?
C6 C7 C8 120.0(14) . . ?
C6 C7 H7 120 . . ?
C8 C7 H7 120 . . ?
C7 C8 C3 119.9(12) . . ?
C7 C8 C9 133.1(11) . . ?
C3 C8 C9 106.7(10) . . ?
C8 C9 C10 107.6(10) . . ?
C8 C9 C11 99.6(10) . . ?
C10 C9 C11 101.0(10) . . ?
C8 C9 H9 115.5 . . ?
C10 C9 H9 115.5 . . ?
C11 C9 H9 115.5 . . ?
C1 C10 C9 101.7(10) . . ?
C1 C10 H10A 111.4 . . ?
C9 C10 H10A 111.4 . . ?
C1 C10 H10B 111.4 . . ?
C9 C10 H10B 111.4 . . ?
H10A C10 H10B 109.3 . . ?
C9 C11 C2 93.9(9) . . ?
C9 C11 H11A 112.9 . . ?
C2 C11 H11A 112.9 . . ?
C9 C11 H11B 112.9 . . ?
C2 C11 H11B 112.9 . . ?
H11A C11 H11B 110.4 . . ?
C1 N12 N13 114.5(10) . . ?
C14 N13 N12 119.9(9) . . ?
C14 N13 H13 120 . . ?
N12 N13 H13 120 . . ?
N13 C14 C15 124.2(10) . . ?
N13 C14 C19 118.5(11) . . ?
C15 C14 C19 117.3(10) . . ?
C14 C15 C16 121.7(10) . . ?
C14 C15 N20 122.4(11) . . ?
C16 C15 N20 115.8(11) . . ?
C17 C16 C15 118.2(11) . . ?
C17 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
C16 C17 C18 122.6(11) . . ?
C16 C17 N23 118.4(12) . . ?
C18 C17 N23 119.0(11) . . ?
C19 C18 C17 119.5(12) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C14 120.7(12) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
O22 N20 O21 123.0(12) . . ?
O22 N20 C15 119.2(12) . . ?
O21 N20 C15 117.8(12) . . ?
O25 N23 O24 123.4(12) . . ?
O25 N23 C17 118.3(13) . . ?
O24 N23 C17 118.3(12) . . ?
N62 C51 C52 123.4(11) . . ?
N62 C51 C60 129.0(11) . . ?
C52 C51 C60 107.5(10) . . ?
C51 C52 C53 104.0(10) . . ?
C51 C52 C61 99.1(11) . . ?
C53 C52 C61 100.6(10) . . ?
C51 C52 H52 116.8 . . ?
C53 C52 H52 116.8 . . ?
C61 C52 H52 116.8 . . ?
C54 C53 C58 119.5(13) . . ?
C54 C53 C52 134.0(13) . . ?
C58 C53 C52 106.4(11) . . ?
C53 C54 C55 119.5(17) . . ?
C53 C54 H54 120.3 . . ?
C55 C54 H54 120.3 . . ?
C54 C55 C56 120.1(18) . . ?
C54 C55 H55 119.9 . . ?
C56 C55 H55 119.9 . . ?
C57 C56 C55 121.3(17) . . ?
C57 C56 H56 119.3 . . ?
C55 C56 H56 119.3 . . ?
C56 C57 C58 119.5(16) . . ?
C56 C57 H57 120.3 . . ?
C58 C57 H57 120.3 . . ?
C57 C58 C53 120.0(13) . . ?
C57 C58 C59 133.6(13) . . ?
C53 C58 C59 106.2(10) . . ?
C58 C59 C61 101.6(11) . . ?
C58 C59 C60 106.7(10) . . ?
C61 C59 C60 101.5(10) . . ?
C58 C59 H59 115.1 . . ?
C61 C59 H59 115.1 . . ?
C60 C59 H59 115.1 . . ?
C51 C60 C59 100.2(9) . . ?
C51 C60 H60A 111.7 . . ?
C59 C60 H60A 111.7 . . ?
C51 C60 H60B 111.7 . . ?
C59 C60 H60B 111.7 . . ?
H60A C60 H60B 109.5 . . ?
C59 C61 C52 93.5(10) . . ?
C59 C61 H61A 113 . . ?
C52 C61 H61A 113 . . ?
C59 C61 H61B 113 . . ?
C52 C61 H61B 113 . . ?
H61A C61 H61B 110.4 . . ?
C51 N62 N63 115.4(10) . . ?
C64 N63 N62 119.3(9) . . ?
C64 N63 H63 120.3 . . ?
N62 N63 H63 120.3 . . ?
N63 C64 C69 119.7(11) . . ?
N63 C64 C65 123.9(11) . . ?
C69 C64 C65 116.4(10) . . ?
C66 C65 C64 122.5(11) . . ?
C66 C65 N70 115.5(12) . . ?
C64 C65 N70 121.9(10) . . ?
C67 C66 C65 117.4(12) . . ?
C67 C66 H66 121.3 . . ?
C65 C66 H66 121.3 . . ?
C66 C67 C68 122.9(10) . . ?
C66 C67 N73 117.8(13) . . ?
C68 C67 N73 119.3(13) . . ?
C69 C68 C67 118.1(11) . . ?
C69 C68 H68 120.9 . . ?
C67 C68 H68 120.9 . . ?
C68 C69 C64 122.4(12) . . ?
C68 C69 H69 118.8 . . ?
C64 C69 H69 118.8 . . ?
O72 N70 O71 120.8(13) . . ?
O72 N70 C65 120.2(11) . . ?
O71 N70 C65 119.0(12) . . ?
O75 N73 O74 124.6(13) . . ?
O75 N73 C67 116.3(14) . . ?
O74 N73 C67 119.1(14) . . ?

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
N12 C1 C2 C3 114.8(12) . . . . ?
C10 C1 C2 C3 -67.3(11) . . . . ?
N12 C1 C2 C11 -141.3(11) . . . . ?
C10 C1 C2 C11 36.6(11) . . . . ?
C1 C2 C3 C4 -108.9(15) . . . . ?
C11 C2 C3 C4 148.5(14) . . . . ?
C1 C2 C3 C8 71.5(11) . . . . ?
C11 C2 C3 C8 -31.1(12) . . . . ?
C8 C3 C4 C5 0(2) . . . . ?
C2 C3 C4 C5 179.9(14) . . . . ?
C3 C4 C5 C6 0(2) . . . . ?
C4 C5 C6 C7 -1(3) . . . . ?
C5 C6 C7 C8 3(2) . . . . ?
C6 C7 C8 C3 -3.0(19) . . . . ?
C6 C7 C8 C9 -175.6(13) . . . . ?
C4 C3 C8 C7 2.0(19) . . . . ?
C2 C3 C8 C7 -178.3(11) . . . . ?
C4 C3 C8 C9 176.4(11) . . . . ?
C2 C3 C8 C9 -3.9(12) . . . . ?
C7 C8 C9 C10 105.9(15) . . . . ?
C3 C8 C9 C10 -67.4(12) . . . . ?
C7 C8 C9 C11 -149.2(14) . . . . ?
C3 C8 C9 C11 37.5(12) . . . . ?
N12 C1 C10 C9 176.7(12) . . . . ?
C2 C1 C10 C9 -1.0(12) . . . . ?
C8 C9 C10 C1 68.5(11) . . . . ?
C11 C9 C10 C1 -35.4(12) . . . . ?
C8 C9 C11 C2 -53.3(11) . . . . ?
C10 C9 C11 C2 56.9(11) . . . . ?
C1 C2 C11 C9 -56.2(11) . . . . ?
C3 C2 C11 C9 51.4(11) . . . . ?
C2 C1 N12 N13 -178.5(10) . . . . ?
C10 C1 N12 N13 4.1(17) . . . . ?
C1 N12 N13 C14 -169.9(11) . . . . ?
N12 N13 C14 C15 -174.9(10) . . . . ?
N12 N13 C14 C19 7.0(16) . . . . ?
N13 C14 C15 C16 -176.4(11) . . . . ?
C19 C14 C15 C16 1.7(16) . . . . ?
N13 C14 C15 N20 5.0(17) . . . . ?
C19 C14 C15 N20 -176.9(11) . . . . ?
C14 C15 C16 C17 -0.9(16) . . . . ?
N20 C15 C16 C17 177.8(10) . . . . ?
C15 C16 C17 C18 0.1(17) . . . . ?
C15 C16 C17 N23 177.3(10) . . . . ?
C16 C17 C18 C19 -0.2(19) . . . . ?
N23 C17 C18 C19 -177.4(12) . . . . ?
C17 C18 C19 C14 1.1(19) . . . . ?
N13 C14 C19 C18 176.4(12) . . . . ?
C15 C14 C19 C18 -1.8(18) . . . . ?
C14 C15 N20 O22 -177.5(13) . . . . ?
C16 C15 N20 O22 3.8(17) . . . . ?
C14 C15 N20 O21 2.9(17) . . . . ?
C16 C15 N20 O21 -175.8(11) . . . . ?
C16 C17 N23 O25 177.1(11) . . . . ?
C18 C17 N23 O25 -5.6(16) . . . . ?
C16 C17 N23 O24 -3.0(16) . . . . ?
C18 C17 N23 O24 174.4(12) . . . . ?
N62 C51 C52 C53 113.5(13) . . . . ?
C60 C51 C52 C53 -68.8(13) . . . . ?
N62 C51 C52 C61 -143.2(12) . . . . ?
C60 C51 C52 C61 34.6(12) . . . . ?
C51 C52 C53 C54 -108.9(16) . . . . ?
C61 C52 C53 C54 148.8(15) . . . . ?
C51 C52 C53 C58 69.8(12) . . . . ?
C61 C52 C53 C58 -32.4(13) . . . . ?
C58 C53 C54 C55 1(2) . . . . ?
C52 C53 C54 C55 179.1(15) . . . . ?
C53 C54 C55 C56 -1(2) . . . . ?
C54 C55 C56 C57 -1(3) . . . . ?
C55 C56 C57 C58 3(2) . . . . ?
C56 C57 C58 C53 -3.1(19) . . . . ?
C56 C57 C58 C59 -178.1(14) . . . . ?
C54 C53 C58 C57 1.6(19) . . . . ?
C52 C53 C58 C57 -177.4(11) . . . . ?
C54 C53 C58 C59 177.7(12) . . . . ?
C52 C53 C58 C59 -1.2(13) . . . . ?
C57 C58 C59 C61 -149.3(14) . . . . ?
C53 C58 C59 C61 35.3(12) . . . . ?
C57 C58 C59 C60 104.9(15) . . . . ?
C53 C58 C59 C60 -70.5(12) . . . . ?
N62 C51 C60 C59 178.8(13) . . . . ?
C52 C51 C60 C59 1.2(13) . . . . ?
C58 C59 C60 C51 68.2(12) . . . . ?
C61 C59 C60 C51 -37.7(12) . . . . ?
C58 C59 C61 C52 -51.9(11) . . . . ?
C60 C59 C61 C52 58.0(11) . . . . ?
C51 C52 C61 C59 -55.5(10) . . . . ?
C53 C52 C61 C59 50.6(11) . . . . ?
C52 C51 N62 N63 178.9(10) . . . . ?
C60 C51 N62 N63 1.7(18) . . . . ?
C51 N62 N63 C64 -162.2(11) . . . . ?
N62 N63 C64 C69 -6.1(16) . . . . ?
N62 N63 C64 C65 174.4(10) . . . . ?
N63 C64 C65 C66 -174.9(11) . . . . ?
C69 C64 C65 C66 5.6(16) . . . . ?
N63 C64 C65 N70 1.4(17) . . . . ?
C69 C64 C65 N70 -178.2(11) . . . . ?
C64 C65 C66 C67 -3.0(17) . . . . ?
N70 C65 C66 C67 -179.5(11) . . . . ?
C65 C66 C67 C68 -1.4(18) . . . . ?
C65 C66 C67 N73 177.7(11) . . . . ?
C66 C67 C68 C69 2.9(18) . . . . ?
N73 C67 C68 C69 -176.2(11) . . . . ?
C67 C68 C69 C64 0.0(18) . . . . ?
N63 C64 C69 C68 176.5(11) . . . . ?
C65 C64 C69 C68 -4.0(16) . . . . ?
C66 C65 N70 O72 -1.1(17) . . . . ?
C64 C65 N70 O72 -177.6(12) . . . . ?
C66 C65 N70 O71 179.9(12) . . . . ?
C64 C65 N70 O71 3.4(17) . . . . ?
C66 C67 N73 O75 -170.1(12) . . . . ?
C68 C67 N73 O75 9.0(18) . . . . ?
C66 C67 N73 O74 7.9(19) . . . . ?
C68 C67 N73 O74 -173.0(13) . . . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC) in cooperation with FIZ Karlsruhe.
# 
# Please note that these data are only for research purposes or private use.
# For detailed information please see under Terms & Conditions.
# Full information about CCDC and FIZ Karlsruhe 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 FIZ Karlsruhe. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_240703-ICSD
_database_code_depnum_ccdc_archive 'CCDC 1711351'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1107/S1600536806051737 2007
_audit_update_record             
;
2018-02-28 deposited with the CCDC.	2024-10-31 downloaded from the CCDC.
;
_database_code_ICSD              240703
_chemical_name_systematic        
;
Lithium Terbium Tetrakis(catena-phosphate(V))
;
_chemical_formula_sum            'Li1 O12 P4 Tb1'
_cell_length_a                   16.358
_cell_length_b                   7.05
_cell_length_c                   9.629
_cell_angle_alpha                90
_cell_angle_beta                 126.15
_cell_angle_gamma                90
_cell_volume                     896.66
_cell_formula_units_Z            4
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_Int_Tables_number      15
_symmetry_cell_setting           monoclinic
_refine_ls_R_factor_all          0.0202
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 'x, -y, z+1/2'
2 '-x, -y, -z'
3 '-x, y, -z+1/2'
4 'x, y, z'
5 'x+1/2, -y+1/2, z+1/2'
6 '-x+1/2, -y+1/2, -z'
7 '-x+1/2, y+1/2, -z+1/2'
8 'x+1/2, y+1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
Li1 Li1+ 0 0.705 0.25
Tb1 Tb3+ 0 0.20252 0.25
P1 P5+ 0.13795 0.553 0.6151
P2 P5+ 0.14715 0.152 0.6974
O1 O2- 0.1137 0.7167 0.6825
O2 O2- 0.0719 0.0871 0.7268
O3 O2- 0.1286 0.1149 0.5286
O4 O2- 0.1578 0.3762 0.734
O5 O2- 0.2555 0.0801 0.8536
O6 O2- 0.0653 0.5027 0.428

#End of data_240703-ICSD


####################################################################### 
# 
# 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_elmds231128
_database_code_depnum_ccdc_archive 'CCDC 2384604'
loop_
_audit_author_name
_audit_author_address
'Gruber Nathalie'
;university of Strasbourg
France
;
_audit_update_record             
;
2024-09-17 deposited with the CCDC.	2024-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 F3 N4 O2 S'
_chemical_formula_sum            'C18 H17 F3 N4 O2 S'
_chemical_formula_weight         410.42

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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.1393(12)
_cell_length_b                   10.5980(18)
_cell_length_c                   13.216(2)
_cell_angle_alpha                87.980(7)
_cell_angle_beta                 88.779(6)
_cell_angle_gamma                76.119(6)
_cell_volume                     970.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5166
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      27.37

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.216
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6918
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  triumph
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17075
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.542
_diffrn_reflns_theta_max         27.907
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4609
_reflns_number_gt                3486
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/3(Sheldrick, 2019)'
_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)+(0.0521P)²+0.1363P] 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         4609
_refine_ls_number_parameters     276
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1060
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.056
_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
N1 N 0.65820(17) 0.22118(11) 0.64869(9) 0.0306(3) Uani 1 1 d . . . . .
S1 S 0.86057(5) 0.17551(4) 0.71200(3) 0.03429(12) Uani 1 1 d . . . . .
O1 O 0.98260(17) 0.07485(13) 0.65623(9) 0.0507(3) Uani 1 1 d . . . . .
O2 O 0.91960(17) 0.29243(12) 0.73040(9) 0.0463(3) Uani 1 1 d . . . . .
C1 C 0.80858(19) 0.10761(15) 0.82977(11) 0.0299(3) Uani 1 1 d . . . . .
C2 C 0.8345(2) -0.02595(15) 0.84076(12) 0.0340(3) Uani 1 1 d . . . . .
H2 H 0.875638 -0.080196 0.784854 0.041 Uiso 1 1 calc R U . . .
C3 C 0.7995(2) -0.07936(16) 0.93458(12) 0.0356(3) Uani 1 1 d . . . . .
H3 H 0.817254 -0.170900 0.942458 0.043 Uiso 1 1 calc R U . . .
C4 C 0.7389(2) -0.00163(16) 1.01725(11) 0.0326(3) Uani 1 1 d . . . . .
C5 C 0.7121(2) 0.13207(16) 1.00375(12) 0.0365(4) Uani 1 1 d . . . . .
H5 H 0.668854 0.186552 1.059311 0.044 Uiso 1 1 calc R U . . .
C6 C 0.7470(2) 0.18757(15) 0.91109(12) 0.0345(3) Uani 1 1 d . . . . .
H6 H 0.729136 0.279109 0.903161 0.041 Uiso 1 1 calc R U . . .
C7 C 0.7039(2) -0.06178(19) 1.11871(12) 0.0436(4) Uani 1 1 d . . . . .
H7A H 0.567097 -0.062049 1.125909 0.065 Uiso 1 1 calc R U . . .
H7B H 0.739463 -0.011148 1.172634 0.065 Uiso 1 1 calc R U . . .
H7C H 0.782417 -0.151298 1.123597 0.065 Uiso 1 1 calc R U . . .
C8 C 0.5331(2) 0.34443(14) 0.66939(11) 0.0290(3) Uani 1 1 d . . . . .
N2 N 0.5716(2) 0.45445(13) 0.61688(11) 0.0398(2) Uani 1 1 d . . . . .
N3 N 0.7128(2) 0.43335(13) 0.55840(11) 0.0398(2) Uani 1 1 d . . . . .
N4 N 0.8369(2) 0.42714(17) 0.50371(13) 0.0554(4) Uani 1 1 d . . . . .
C9 C 0.3790(2) 0.35765(15) 0.72945(12) 0.0342(3) Uani 1 1 d . . . . .
H9 H 0.359036 0.281952 0.764326 0.041 Uiso 1 1 calc R U . . .
C10 C 0.2349(2) 0.48267(17) 0.74624(14) 0.0427(4) Uani 1 1 d . . . . .
H10A H 0.270160 0.552015 0.703193 0.051 Uiso 1 1 calc R U . . .
H10B H 0.106535 0.474180 0.724935 0.051 Uiso 1 1 calc R U . . .
C11 C 0.2224(4) 0.5216(2) 0.85318(18) 0.0688(6) Uani 1 1 d D U . . .
F1 F 0.208(4) 0.4296(12) 0.9237(12) 0.098(3) Uani 0.51(5) 1 d D U P A 1
F2 F 0.3883(14) 0.5548(14) 0.8762(12) 0.077(2) Uani 0.51(5) 1 d D . P A 1
F3 F 0.076(2) 0.6263(11) 0.8632(11) 0.100(3) Uani 0.51(5) 1 d D . P A 1
F1A F 0.099(2) 0.6358(11) 0.8713(14) 0.104(4) Uani 0.49(5) 1 d D . P A 2
F2A F 0.149(3) 0.4327(12) 0.9080(14) 0.089(3) Uani 0.49(5) 1 d D . P A 2
F3A F 0.3862(18) 0.527(2) 0.8980(16) 0.104(3) Uani 0.49(5) 1 d D U P A 2
C12 C 0.5703(2) 0.12201(14) 0.60433(12) 0.0354(3) Uani 1 1 d . . . . .
H12A H 0.458450 0.111183 0.646393 0.042 Uiso 1 1 calc R U . . .
H12B H 0.665929 0.037227 0.603152 0.042 Uiso 1 1 calc R U . . .
C13 C 0.5056(2) 0.16495(14) 0.49825(11) 0.0310(3) Uani 1 1 d . . . . .
C14 C 0.6408(3) 0.15891(16) 0.42048(13) 0.0411(4) Uani 1 1 d . . . . .
H14 H 0.774003 0.126209 0.434202 0.049 Uiso 1 1 calc R U . . .
C15 C 0.5833(3) 0.19997(19) 0.32351(14) 0.0527(5) Uani 1 1 d . . . . .
H15 H 0.677068 0.195267 0.270801 0.063 Uiso 1 1 calc R U . . .
C16 C 0.3913(4) 0.24764(18) 0.30263(14) 0.0584(6) Uani 1 1 d . . . . .
H16 H 0.352611 0.275873 0.235610 0.070 Uiso 1 1 calc R U . . .
C17 C 0.2553(3) 0.25457(18) 0.37840(15) 0.0530(5) Uani 1 1 d . . . . .
H17 H 0.122470 0.287751 0.363819 0.064 Uiso 1 1 calc R U . . .
C18 C 0.3115(2) 0.21302(16) 0.47665(13) 0.0396(4) Uani 1 1 d . . . . .
H18 H 0.217000 0.217565 0.528975 0.047 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
N1 C8 1.4262(18) . ?
N1 C12 1.4892(19) . ?
N1 S1 1.6460(12) . ?
S1 O1 1.4221(13) . ?
S1 O2 1.4313(13) . ?
S1 C1 1.7615(15) . ?
C1 C2 1.386(2) . ?
C1 C6 1.390(2) . ?
C2 C3 1.388(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(2) . ?
C4 C7 1.506(2) . ?
C5 C6 1.384(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.325(2) . ?
C8 N2 1.4162(19) . ?
N2 N3 1.2389(19) . ?
N3 N4 1.1223(19) . ?
C9 C10 1.490(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.481(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 F3A 1.337(10) . ?
C11 F3 1.339(8) . ?
C11 F1A 1.340(10) . ?
C11 F1 1.345(10) . ?
C11 F2 1.357(9) . ?
C11 F2A 1.362(10) . ?
C12 C13 1.506(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.387(2) . ?
C13 C18 1.389(2) . ?
C14 C15 1.377(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.373(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.372(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(3) . ?
C17 H17 0.9500 . ?
C18 H18 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
C8 N1 C12 117.29(12) . . ?
C8 N1 S1 118.25(9) . . ?
C12 N1 S1 120.13(10) . . ?
O1 S1 O2 120.28(8) . . ?
O1 S1 N1 106.41(7) . . ?
O2 S1 N1 105.78(7) . . ?
O1 S1 C1 107.75(7) . . ?
O2 S1 C1 107.99(7) . . ?
N1 S1 C1 108.12(7) . . ?
C2 C1 C6 120.73(14) . . ?
C2 C1 S1 119.28(12) . . ?
C6 C1 S1 119.97(12) . . ?
C1 C2 C3 119.07(14) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 121.33(15) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 118.35(14) . . ?
C5 C4 C7 121.20(15) . . ?
C3 C4 C7 120.45(15) . . ?
C6 C5 C4 121.39(15) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 119.12(15) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 N2 120.00(14) . . ?
C9 C8 N1 122.82(14) . . ?
N2 C8 N1 117.04(13) . . ?
N3 N2 C8 116.19(13) . . ?
N4 N3 N2 173.15(17) . . ?
C8 C9 C10 124.72(15) . . ?
C8 C9 H9 117.6 . . ?
C10 C9 H9 117.6 . . ?
C11 C10 C9 112.93(17) . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
F3A C11 F1A 105.1(8) . . ?
F3 C11 F1 110.2(9) . . ?
F3 C11 F2 108.4(8) . . ?
F1 C11 F2 104.0(8) . . ?
F3A C11 F2A 106.5(7) . . ?
F1A C11 F2A 104.4(8) . . ?
F3A C11 C10 117.6(9) . . ?
F3 C11 C10 108.7(7) . . ?
F1A C11 C10 115.0(8) . . ?
F1 C11 C10 116.7(8) . . ?
F2 C11 C10 108.5(6) . . ?
F2A C11 C10 107.2(8) . . ?
N1 C12 C13 109.50(12) . . ?
N1 C12 H12A 109.8 . . ?
C13 C12 H12A 109.8 . . ?
N1 C12 H12B 109.8 . . ?
C13 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
C14 C13 C18 118.88(15) . . ?
C14 C13 C12 120.06(14) . . ?
C18 C13 C12 121.05(14) . . ?
C15 C14 C13 120.51(17) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 120.37(18) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 120.09(17) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.09(18) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 120.07(17) . . ?
C13 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?

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
C8 N1 S1 O1 -161.54(11) . . . . ?
C12 N1 S1 O1 42.48(13) . . . . ?
C8 N1 S1 O2 -32.53(13) . . . . ?
C12 N1 S1 O2 171.49(11) . . . . ?
C8 N1 S1 C1 82.95(12) . . . . ?
C12 N1 S1 C1 -73.04(13) . . . . ?
O1 S1 C1 C2 -19.22(14) . . . . ?
O2 S1 C1 C2 -150.57(12) . . . . ?
N1 S1 C1 C2 95.41(12) . . . . ?
O1 S1 C1 C6 159.16(12) . . . . ?
O2 S1 C1 C6 27.82(14) . . . . ?
N1 S1 C1 C6 -86.20(13) . . . . ?
C6 C1 C2 C3 -0.5(2) . . . . ?
S1 C1 C2 C3 177.89(11) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C2 C3 C4 C7 -179.29(14) . . . . ?
C3 C4 C5 C6 -0.9(2) . . . . ?
C7 C4 C5 C6 178.94(14) . . . . ?
C4 C5 C6 C1 0.6(2) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
S1 C1 C6 C5 -178.20(11) . . . . ?
C12 N1 C8 C9 57.35(19) . . . . ?
S1 N1 C8 C9 -99.32(15) . . . . ?
C12 N1 C8 N2 -118.21(14) . . . . ?
S1 N1 C8 N2 85.12(15) . . . . ?
C9 C8 N2 N3 -176.57(14) . . . . ?
N1 C8 N2 N3 -0.9(2) . . . . ?
N2 C8 C9 C10 1.0(2) . . . . ?
N1 C8 C9 C10 -174.40(14) . . . . ?
C8 C9 C10 C11 -118.8(2) . . . . ?
C9 C10 C11 F3A 53.2(12) . . . . ?
C9 C10 C11 F3 -173.2(8) . . . . ?
C9 C10 C11 F1A 177.8(8) . . . . ?
C9 C10 C11 F1 -47.8(13) . . . . ?
C9 C10 C11 F2 69.2(7) . . . . ?
C9 C10 C11 F2A -66.6(9) . . . . ?
C8 N1 C12 C13 68.02(17) . . . . ?
S1 N1 C12 C13 -135.77(12) . . . . ?
N1 C12 C13 C14 73.66(17) . . . . ?
N1 C12 C13 C18 -105.25(16) . . . . ?
C18 C13 C14 C15 0.0(2) . . . . ?
C12 C13 C14 C15 -178.92(15) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C14 C13 C18 C17 -0.2(2) . . . . ?
C12 C13 C18 C17 178.73(15) . . . . ?
C16 C17 C18 C13 0.3(3) . . . . ?

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.041



####################################################################### 
# 
# 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_elmmh230301sq
_database_code_depnum_ccdc_archive 'CCDC 2384608'
loop_
_audit_author_name
_audit_author_address
Gruber
;university of Strasbourg
France
;
_audit_update_record             
;
2024-09-17 deposited with the CCDC.	2024-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H17 F3 N4 O4 S,solvent'
_chemical_formula_sum            'C19 H17 F3 N4 O4 S,solvent'
_chemical_formula_weight         454.42

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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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                   5.5258(4)
_cell_length_b                   19.0765(13)
_cell_length_c                   21.2903(18)
_cell_angle_alpha                90
_cell_angle_beta                 94.338(3)
_cell_angle_gamma                90
_cell_volume                     2237.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6778
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      22.91

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.201
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7138
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  triumph
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44897
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.435
_diffrn_reflns_theta_max         27.921
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5345
_reflns_number_gt                3634
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0627P)²+0.3887P] 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         5345
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1245
_refine_ls_wR_factor_gt          0.1104
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.044
_refine_ls_shift/su_mean         0.001

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
N1 N 0.8271(3) 0.42302(7) 0.35316(7) 0.0282(3) Uani 1 1 d . . . . .
S1 S 1.00638(8) 0.39072(2) 0.41264(2) 0.02879(13) Uani 1 1 d . . . . .
O1 O 1.1547(2) 0.33923(7) 0.38540(7) 0.0362(3) Uani 1 1 d . . . . .
O2 O 1.1188(2) 0.44957(7) 0.44459(7) 0.0398(3) Uani 1 1 d . . . . .
C1 C 0.8130(3) 0.34832(9) 0.46205(9) 0.0288(4) Uani 1 1 d . . . . .
C2 C 0.7528(4) 0.27795(10) 0.45152(10) 0.0362(4) Uani 1 1 d . . . . .
H2 H 0.825449 0.251897 0.419885 0.043 Uiso 1 1 calc R U . . .
C3 C 0.5866(4) 0.24700(11) 0.48776(10) 0.0425(5) Uani 1 1 d . . . . .
H3 H 0.547255 0.198965 0.481113 0.051 Uiso 1 1 calc R U . . .
C4 C 0.4751(4) 0.28384(12) 0.53362(10) 0.0404(5) Uani 1 1 d . . . . .
C5 C 0.5382(4) 0.35366(12) 0.54301(10) 0.0426(5) Uani 1 1 d . . . . .
H5 H 0.463906 0.379720 0.574345 0.051 Uiso 1 1 calc R U . . .
C6 C 0.7060(4) 0.38630(10) 0.50809(9) 0.0350(4) Uani 1 1 d . . . . .
H6 H 0.747599 0.434068 0.515482 0.042 Uiso 1 1 calc R U . . .
C7 C 0.2891(4) 0.24906(14) 0.57201(12) 0.0594(7) Uani 1 1 d . . . . .
H7A H 0.355284 0.204980 0.589597 0.089 Uiso 1 1 calc R U . . .
H7B H 0.141518 0.239402 0.544926 0.089 Uiso 1 1 calc R U . . .
H7C H 0.250063 0.280290 0.606375 0.089 Uiso 1 1 calc R U . . .
C8 C 0.6872(3) 0.36996(10) 0.31902(9) 0.0314(4) Uani 1 1 d . . . . .
H8 H 0.531187 0.358919 0.332150 0.038 Uiso 1 1 calc R U . . .
C9 C 0.7638(3) 0.33565(10) 0.27032(9) 0.0333(4) Uani 1 1 d . . . . .
N2 N 0.6030(3) 0.28232(10) 0.24447(9) 0.0458(5) Uani 1 1 d . . . . .
N3 N 0.6908(3) 0.23802(9) 0.20994(9) 0.0420(4) Uani 1 1 d . . . . .
N4 N 0.7470(4) 0.19501(10) 0.17815(10) 0.0567(5) Uani 1 1 d . . . . .
C10 C 0.9965(4) 0.34925(11) 0.24058(10) 0.0396(5) Uani 1 1 d . . . . .
H10A H 1.103358 0.378270 0.269522 0.048 Uiso 1 1 calc R U . . .
H10B H 1.079717 0.304031 0.234699 0.048 Uiso 1 1 calc R U . . .
C11 C 0.9605(5) 0.38570(12) 0.17830(12) 0.0499(6) Uani 1 1 d . . . . .
F004 F 0.8345(3) 0.34806(8) 0.13441(7) 0.0696(4) Uani 1 1 d . . . . .
F005 F 0.8469(3) 0.44689(7) 0.18301(8) 0.0718(5) Uani 1 1 d . . . . .
F006 F 1.1730(3) 0.39965(8) 0.15518(7) 0.0718(5) Uani 1 1 d . . . . .
C12 C 0.6793(3) 0.48557(9) 0.36959(10) 0.0338(4) Uani 1 1 d . . . . .
H12A H 0.772697 0.514321 0.401649 0.041 Uiso 1 1 calc R U . . .
H12B H 0.528556 0.469754 0.387609 0.041 Uiso 1 1 calc R U . . .
C13 C 0.6163(3) 0.52901(9) 0.31165(10) 0.0322(4) Uani 1 1 d . . . . .
C14 C 0.3993(4) 0.51968(10) 0.27634(11) 0.0399(5) Uani 1 1 d . . . . .
H14 H 0.285594 0.486882 0.290271 0.048 Uiso 1 1 calc R U . . .
C15 C 0.3412(4) 0.55678(11) 0.22085(12) 0.0455(5) Uani 1 1 d . . . . .
H15 H 0.192148 0.549542 0.196443 0.055 Uiso 1 1 calc R U . . .
C16 C 0.5080(4) 0.60379(10) 0.20339(11) 0.0407(5) Uani 1 1 d . . . . .
O3 O 0.4920(3) 0.64821(8) 0.15194(8) 0.0568(4) Uani 1 1 d . . . . .
C17 C 0.7226(5) 0.68099(14) 0.15277(14) 0.0645(7) Uani 1 1 d . . . . .
H17A H 0.702331 0.732055 0.145973 0.077 Uiso 1 1 calc R U . . .
H17B H 0.814876 0.661853 0.118555 0.077 Uiso 1 1 calc R U . . .
O4 O 0.8515(3) 0.66830(8) 0.21224(8) 0.0566(5) Uani 1 1 d . . . . .
C18 C 0.7227(4) 0.61542(10) 0.23912(11) 0.0393(5) Uani 1 1 d . . . . .
C19 C 0.7835(3) 0.57891(10) 0.29335(10) 0.0371(5) Uani 1 1 d . . . . .
H19 H 0.932469 0.587018 0.317536 0.045 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
N1 C8 1.437(2) . ?
N1 C12 1.502(2) . ?
N1 S1 1.6659(16) . ?
S1 O2 1.4301(14) . ?
S1 O1 1.4301(13) . ?
S1 C1 1.7529(18) . ?
C1 C6 1.387(3) . ?
C1 C2 1.397(3) . ?
C2 C3 1.376(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C4 C7 1.514(3) . ?
C5 C6 1.380(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.322(3) . ?
C8 H8 0.9500 . ?
C9 N2 1.433(3) . ?
C9 C10 1.498(3) . ?
N2 N3 1.243(2) . ?
N3 N4 1.122(2) . ?
C10 C11 1.497(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 F004 1.332(3) . ?
C11 F005 1.333(3) . ?
C11 F006 1.334(3) . ?
C12 C13 1.505(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.378(3) . ?
C13 C19 1.402(3) . ?
C14 C15 1.394(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.358(3) . ?
C15 H15 0.9500 . ?
C16 C18 1.378(3) . ?
C16 O3 1.382(2) . ?
O3 C17 1.418(3) . ?
C17 O4 1.426(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
O4 C18 1.383(2) . ?
C18 C19 1.368(3) . ?
C19 H19 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
C8 N1 C12 113.34(14) . . ?
C8 N1 S1 112.97(12) . . ?
C12 N1 S1 114.80(13) . . ?
O2 S1 O1 119.36(8) . . ?
O2 S1 N1 106.45(8) . . ?
O1 S1 N1 105.78(8) . . ?
O2 S1 C1 109.84(9) . . ?
O1 S1 C1 108.70(8) . . ?
N1 S1 C1 105.80(8) . . ?
C6 C1 C2 120.43(18) . . ?
C6 C1 S1 119.67(14) . . ?
C2 C1 S1 119.70(15) . . ?
C3 C2 C1 118.88(19) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 121.94(19) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 117.90(18) . . ?
C3 C4 C7 121.0(2) . . ?
C5 C4 C7 121.1(2) . . ?
C6 C5 C4 121.84(19) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 119.00(18) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 N1 123.60(17) . . ?
C9 C8 H8 118.2 . . ?
N1 C8 H8 118.2 . . ?
C8 C9 N2 115.24(17) . . ?
C8 C9 C10 125.56(18) . . ?
N2 C9 C10 119.19(17) . . ?
N3 N2 C9 116.82(17) . . ?
N4 N3 N2 172.8(2) . . ?
C11 C10 C9 113.21(18) . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
F004 C11 F005 107.5(2) . . ?
F004 C11 F006 106.06(18) . . ?
F005 C11 F006 106.60(19) . . ?
F004 C11 C10 113.46(19) . . ?
F005 C11 C10 111.83(19) . . ?
F006 C11 C10 111.0(2) . . ?
N1 C12 C13 110.04(15) . . ?
N1 C12 H12A 109.7 . . ?
C13 C12 H12A 109.7 . . ?
N1 C12 H12B 109.7 . . ?
C13 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C14 C13 C19 120.04(19) . . ?
C14 C13 C12 120.93(17) . . ?
C19 C13 C12 119.02(18) . . ?
C13 C14 C15 122.16(19) . . ?
C13 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C16 C15 C14 116.7(2) . . ?
C16 C15 H15 121.6 . . ?
C14 C15 H15 121.6 . . ?
C15 C16 C18 121.9(2) . . ?
C15 C16 O3 128.2(2) . . ?
C18 C16 O3 109.84(18) . . ?
C16 O3 C17 104.89(18) . . ?
O3 C17 O4 108.93(19) . . ?
O3 C17 H17A 109.9 . . ?
O4 C17 H17A 109.9 . . ?
O3 C17 H17B 109.9 . . ?
O4 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
C18 O4 C17 104.65(17) . . ?
C19 C18 C16 122.01(19) . . ?
C19 C18 O4 128.25(19) . . ?
C16 C18 O4 109.73(18) . . ?
C18 C19 C13 117.07(19) . . ?
C18 C19 H19 121.5 . . ?
C13 C19 H19 121.5 . . ?

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
C8 N1 S1 O2 -175.82(12) . . . . ?
C12 N1 S1 O2 -43.76(14) . . . . ?
C8 N1 S1 O1 56.24(13) . . . . ?
C12 N1 S1 O1 -171.69(12) . . . . ?
C8 N1 S1 C1 -58.98(14) . . . . ?
C12 N1 S1 C1 73.08(14) . . . . ?
O2 S1 C1 C6 28.05(18) . . . . ?
O1 S1 C1 C6 160.31(15) . . . . ?
N1 S1 C1 C6 -86.47(16) . . . . ?
O2 S1 C1 C2 -156.99(15) . . . . ?
O1 S1 C1 C2 -24.73(18) . . . . ?
N1 S1 C1 C2 88.49(16) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
S1 C1 C2 C3 -175.17(16) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C2 C3 C4 C7 178.8(2) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C7 C4 C5 C6 -179.5(2) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
S1 C1 C6 C5 174.49(16) . . . . ?
C12 N1 C8 C9 137.99(19) . . . . ?
S1 N1 C8 C9 -89.2(2) . . . . ?
N1 C8 C9 N2 177.10(17) . . . . ?
N1 C8 C9 C10 -4.2(3) . . . . ?
C8 C9 N2 N3 -162.64(19) . . . . ?
C10 C9 N2 N3 18.6(3) . . . . ?
C8 C9 C10 C11 -106.0(2) . . . . ?
N2 C9 C10 C11 72.6(2) . . . . ?
C9 C10 C11 F004 -63.7(2) . . . . ?
C9 C10 C11 F005 58.1(2) . . . . ?
C9 C10 C11 F006 176.99(17) . . . . ?
C8 N1 C12 C13 -73.51(19) . . . . ?
S1 N1 C12 C13 154.61(13) . . . . ?
N1 C12 C13 C14 94.3(2) . . . . ?
N1 C12 C13 C19 -84.9(2) . . . . ?
C19 C13 C14 C15 2.3(3) . . . . ?
C12 C13 C14 C15 -176.88(18) . . . . ?
C13 C14 C15 C16 -0.9(3) . . . . ?
C14 C15 C16 C18 -1.1(3) . . . . ?
C14 C15 C16 O3 -178.0(2) . . . . ?
C15 C16 O3 C17 -174.8(2) . . . . ?
C18 C16 O3 C17 8.0(3) . . . . ?
C16 O3 C17 O4 -13.6(3) . . . . ?
O3 C17 O4 C18 13.9(3) . . . . ?
C15 C16 C18 C19 1.9(3) . . . . ?
O3 C16 C18 C19 179.27(19) . . . . ?
C15 C16 C18 O4 -176.79(19) . . . . ?
O3 C16 C18 O4 0.6(3) . . . . ?
C17 O4 C18 C19 172.6(2) . . . . ?
C17 O4 C18 C16 -8.9(2) . . . . ?
C16 C18 C19 C13 -0.5(3) . . . . ?
O4 C18 C19 C13 177.9(2) . . . . ?
C14 C13 C19 C18 -1.5(3) . . . . ?
C12 C13 C19 C18 177.66(17) . . . . ?

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.049




