# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_NM077
_database_code_depnum_ccdc_archive 'CCDC 2204831'
loop_
_audit_author_name
_audit_author_address
'Thierry ROISNEL'
;Institut des Sciences Chimiques de Rennes
France
;
_audit_update_record             
;
2022-09-01 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 06 avril 2021                                            #
#------------------------------------------------------------------------------#


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H17 F2 N O3'
_chemical_formula_sum            'C18 H17 F2 N O3'
_chemical_formula_weight         333.33
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#


_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0170(11)
_cell_length_b                   11.7369(15)
_cell_length_c                   17.176(2)
_cell_angle_alpha                70.454(4)
_cell_angle_beta                 81.368(4)
_cell_angle_gamma                75.963(4)
_cell_volume                     1657.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6911
_cell_measurement_theta_min      2.3340
_cell_measurement_theta_max      26.9857
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0572562
_diffrn_orient_matrix_UB_21      0.0986002
_diffrn_orient_matrix_UB_31      0.0115128
_diffrn_orient_matrix_UB_12      -0.0475973
_diffrn_orient_matrix_UB_22      0.0145760
_diffrn_orient_matrix_UB_32      -0.0778600
_diffrn_orient_matrix_UB_13      -0.0376921
_diffrn_orient_matrix_UB_23      0.0108750
_diffrn_orient_matrix_UB_33      0.0479369


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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.630
_exptl_crystal_size_mid          0.550
_exptl_crystal_size_min          0.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             696
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.626
_exptl_absorpt_correction_T_max  0.951

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

# Software                   : BIS 2014.5.0.0/23-May-2014 && APEX2_2014.11-0   #
# Number of scans            :        3                                        #
# Total number of frames     :      570                                        #
# Total length of scans      :   570.00 (deg.)                                 #
# Rotation speed             :     5.00 sec./deg.                              #
# Total exposition time      :         47.5 min.                               #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range  Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Omega    5.0  1.00    35.0   105  105.0   14.9   14.5    0.0  305.3 150.0 #
#  2 Phi      5.0  1.00    35.0   360  360.0   14.9   10.4  360.0  337.0 150.0 #
#  3 Omega    5.0  1.00    35.0   105  105.0   14.9   14.5  120.0  305.3 150.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0479
_diffrn_reflns_av_r_equivalents  0.0379
_diffrn_reflns_number            21285
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.912
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.963
_reflns_number_total             7335
_reflns_number_gt                5203
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'

#------------------------------------------------------------------------------#
#                            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     
'w=1/[σ²(Fo²)+(0.0909P)²+0.2133P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7335
_refine_ls_number_parameters     443
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1511
_refine_ls_wR_factor_gt          0.1316
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_restrained_S_all      0.977
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.046

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 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'

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 0.19994(16) 0.25828(12) 0.72798(8) 0.0504(3) Uani 1 1 d . . . . .
C2 C 0.2572(2) 0.33886(18) 0.75019(11) 0.0302(4) Uani 1 1 d . . . . .
C3 C 0.2192(2) 0.46202(19) 0.70737(11) 0.0327(4) Uani 1 1 d . . . . .
H3 H 0.156378 0.490551 0.662147 0.039 Uiso 1 1 calc R U . . .
C4 C 0.2748(2) 0.54394(19) 0.73175(12) 0.0357(5) Uani 1 1 d . . . . .
H4 H 0.250195 0.629860 0.702790 0.043 Uiso 1 1 calc R U . . .
C5 C 0.3658(2) 0.50202(17) 0.79782(11) 0.0304(4) Uani 1 1 d . . . . .
H5 H 0.402542 0.558713 0.814745 0.036 Uiso 1 1 calc R U . . .
C6 C 0.40262(19) 0.37666(16) 0.83896(10) 0.0236(4) Uani 1 1 d . . . . .
C7 C 0.3496(2) 0.29303(17) 0.81528(11) 0.0275(4) Uani 1 1 d . . . . .
H7 H 0.376048 0.206800 0.843017 0.033 Uiso 1 1 calc R U . . .
N8 N 0.49751(16) 0.33149(14) 0.90847(8) 0.0238(3) Uani 1 1 d . . . . .
C9 C 0.4244(2) 0.29211(17) 0.98752(10) 0.0248(4) Uani 1 1 d . . . . .
O10 O 0.28552(14) 0.31686(13) 0.99710(8) 0.0359(3) Uani 1 1 d . . . . .
C11 C 0.51688(19) 0.21437(16) 1.05872(10) 0.0242(4) Uani 1 1 d . . . . .
C12 C 0.4835(2) 0.24262(18) 1.13286(11) 0.0292(4) Uani 1 1 d . . . . .
H12 H 0.406595 0.312777 1.135931 0.035 Uiso 1 1 calc R U . . .
C13 C 0.5610(2) 0.16961(19) 1.20198(12) 0.0355(5) Uani 1 1 d . . . . .
H13 H 0.538590 0.190831 1.251835 0.043 Uiso 1 1 calc R U . . .
C14 C 0.6713(2) 0.06559(19) 1.19889(12) 0.0365(5) Uani 1 1 d . . . . .
H14 H 0.723759 0.015340 1.246679 0.044 Uiso 1 1 calc R U . . .
C15 C 0.7049(2) 0.03506(18) 1.12647(12) 0.0349(5) Uani 1 1 d . . . . .
H15 H 0.780311 -0.036009 1.123686 0.042 Uiso 1 1 calc R U . . .
C16 C 0.6270(2) 0.10953(17) 1.05830(11) 0.0285(4) Uani 1 1 d . . . . .
F17 F 0.65965(14) 0.07861(11) 0.98732(7) 0.0417(3) Uani 1 1 d . . . . .
C18 C 0.65440(19) 0.33810(16) 0.88908(11) 0.0235(4) Uani 1 1 d . . . . .
O19 O 0.71601(14) 0.34066(12) 0.82185(7) 0.0315(3) Uani 1 1 d . . . . .
O20 O 0.71267(13) 0.34515(11) 0.95308(7) 0.0247(3) Uani 1 1 d . . . . .
C21 C 0.88026(19) 0.33895(17) 0.95285(11) 0.0255(4) Uani 1 1 d . . . . .
C22 C 0.9720(2) 0.21891(18) 0.94032(14) 0.0358(5) Uani 1 1 d . . . . .
H22A H 0.935238 0.149159 0.981943 0.054 Uiso 1 1 calc R U . . .
H22B H 1.080675 0.211769 0.946130 0.054 Uiso 1 1 calc R U . . .
H22C H 0.959525 0.218229 0.884790 0.054 Uiso 1 1 calc R U . . .
C23 C 0.8910(2) 0.3427(2) 1.03896(12) 0.0339(4) Uani 1 1 d . . . . .
H23A H 0.826348 0.419303 1.045938 0.051 Uiso 1 1 calc R U . . .
H23B H 0.997681 0.339445 1.046610 0.051 Uiso 1 1 calc R U . . .
H23C H 0.856061 0.271646 1.080125 0.051 Uiso 1 1 calc R U . . .
C24 C 0.9252(2) 0.45163(18) 0.88718(12) 0.0338(4) Uani 1 1 d . . . . .
H24A H 0.914285 0.448392 0.832091 0.051 Uiso 1 1 calc R U . . .
H24B H 1.031975 0.452405 0.891741 0.051 Uiso 1 1 calc R U . . .
H24C H 0.858340 0.526758 0.895370 0.051 Uiso 1 1 calc R U . . .
F51 F -0.26983(17) 0.64811(14) 0.73389(7) 0.0602(4) Uani 1 1 d . . . . .
C52 C -0.2297(2) 0.6373(2) 0.65702(11) 0.0364(5) Uani 1 1 d . . . . .
C53 C -0.2792(2) 0.55172(19) 0.63556(13) 0.0388(5) Uani 1 1 d . . . . .
H53 H -0.338555 0.497943 0.674181 0.047 Uiso 1 1 calc R U . . .
C54 C -0.2405(2) 0.54561(19) 0.55653(13) 0.0386(5) Uani 1 1 d . . . . .
H54 H -0.275298 0.487702 0.539881 0.046 Uiso 1 1 calc R U . . .
C55 C -0.1521(2) 0.62200(17) 0.50085(12) 0.0307(4) Uani 1 1 d . . . . .
H55 H -0.125336 0.616302 0.446442 0.037 Uiso 1 1 calc R U . . .
C56 C -0.10278(19) 0.70686(16) 0.52482(10) 0.0238(4) Uani 1 1 d . . . . .
C57 C -0.1407(2) 0.71653(18) 0.60345(11) 0.0307(4) Uani 1 1 d . . . . .
H57 H -0.107390 0.774972 0.620242 0.037 Uiso 1 1 calc R U . . .
N58 N -0.00828(16) 0.78684(14) 0.46711(9) 0.0261(3) Uani 1 1 d . . . . .
C59 C -0.0817(2) 0.88366(17) 0.40296(12) 0.0286(4) Uani 1 1 d . . . . .
O60 O -0.22062(15) 0.91170(13) 0.40618(9) 0.0420(4) Uani 1 1 d . . . . .
C61A C 0.0119(2) 0.94402(17) 0.32777(11) 0.0275(4) Uani 0.785(2) 1 d . . P A 1
C62A C 0.1053(2) 0.87934(19) 0.27794(12) 0.0344(5) Uani 0.785(2) 1 d . . P A 1
H62A H 0.119266 0.791904 0.294635 0.041 Uiso 0.785(2) 1 calc R U P A 1
C63A C 0.1780(3) 0.9398(2) 0.20468(13) 0.0408(5) Uani 0.785(2) 1 d . . P A 1
H63A H 0.240862 0.894367 0.170925 0.049 Uiso 0.785(2) 1 calc R U P A 1
C64A C 0.1590(3) 1.0672(2) 0.18054(13) 0.0439(6) Uani 0.785(2) 1 d . . P A 1
H64A H 0.210001 1.108968 0.130342 0.053 Uiso 0.785(2) 1 calc R U P A 1
C65A C 0.0665(3) 1.1341(2) 0.22884(12) 0.0392(5) Uani 0.785(2) 1 d . . P A 1
H65A H 0.053686 1.221413 0.212743 0.047 Uiso 0.785(2) 1 calc R U P A 1
C66A C -0.0061(2) 1.07112(18) 0.30048(12) 0.0324(4) Uani 0.785(2) 1 d . . P A 1
F67A F -0.09152(18) 1.13458(13) 0.34894(10) 0.0433(4) Uani 0.785(2) 1 d . . P A
1
C61B C 0.0119(2) 0.94402(17) 0.32777(11) 0.0275(4) Uani 0.215(2) 1 d . . P A 2
C62B C 0.1053(2) 0.87934(19) 0.27794(12) 0.0344(5) Uani 0.215(2) 1 d . . P A 2
C63B C 0.1780(3) 0.9398(2) 0.20468(13) 0.0408(5) Uani 0.215(2) 1 d . . P A 2
H63B H 0.240862 0.894367 0.170925 0.049 Uiso 0.215(2) 1 calc R U P A 2
C64B C 0.1590(3) 1.0672(2) 0.18054(13) 0.0439(6) Uani 0.215(2) 1 d . . P A 2
H64B H 0.210001 1.108968 0.130342 0.053 Uiso 0.215(2) 1 calc R U P A 2
C65B C 0.0665(3) 1.1341(2) 0.22884(12) 0.0392(5) Uani 0.215(2) 1 d . . P A 2
H65B H 0.053686 1.221413 0.212743 0.047 Uiso 0.215(2) 1 calc R U P A 2
C66B C -0.0061(2) 1.07112(18) 0.30048(12) 0.0324(4) Uani 0.215(2) 1 d . . P A 2
H66B H -0.072113 1.117023 0.333012 0.039 Uiso 0.215(2) 1 calc R U P A 2
F67B F 0.1305(6) 0.7600(5) 0.3162(4) 0.0433(4) Uani 0.215(2) 1 d . . P A 2
C68 C 0.1461(2) 0.76404(17) 0.48515(11) 0.0247(4) Uani 1 1 d . . . . .
O69 O 0.20333(15) 0.66829(12) 0.53269(8) 0.0341(3) Uani 1 1 d . . . . .
O70 O 0.20846(13) 0.86059(11) 0.44581(8) 0.0272(3) Uani 1 1 d . . . . .
C71 C 0.37807(19) 0.84988(17) 0.44280(12) 0.0284(4) Uani 1 1 d . . . . .
C72 C 0.4258(2) 0.8253(2) 0.52851(12) 0.0365(5) Uani 1 1 d . . . . .
H72A H 0.362682 0.887459 0.552744 0.055 Uiso 1 1 calc R U . . .
H72B H 0.533926 0.829575 0.524921 0.055 Uiso 1 1 calc R U . . .
H72C H 0.411798 0.742855 0.563486 0.055 Uiso 1 1 calc R U . . .
C73 C 0.3952(2) 0.9773(2) 0.38704(15) 0.0470(6) Uani 1 1 d . . . . .
H73A H 0.354628 0.993594 0.333669 0.071 Uiso 1 1 calc R U . . .
H73B H 0.503930 0.981572 0.378167 0.071 Uiso 1 1 calc R U . . .
H73C H 0.338293 1.039146 0.413149 0.071 Uiso 1 1 calc R U . . .
C74 C 0.4603(2) 0.7507(2) 0.40459(14) 0.0417(5) Uani 1 1 d . . . . .
H74A H 0.447005 0.669675 0.442485 0.063 Uiso 1 1 calc R U . . .
H74B H 0.569735 0.752488 0.394466 0.063 Uiso 1 1 calc R U . . .
H74C H 0.417514 0.765655 0.352034 0.063 Uiso 1 1 calc R U . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.358(2) . ?
C2 C3 1.368(3) . ?
C2 C7 1.376(3) . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(2) . ?
C6 N8 1.450(2) . ?
C7 H7 0.9500 . ?
N8 C9 1.397(2) . ?
N8 C18 1.419(2) . ?
C9 O10 1.214(2) . ?
C9 C11 1.488(2) . ?
C11 C16 1.382(3) . ?
C11 C12 1.393(2) . ?
C12 C13 1.382(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(3) . ?
C15 H15 0.9500 . ?
C16 F17 1.357(2) . ?
C18 O19 1.198(2) . ?
C18 O20 1.322(2) . ?
O20 C21 1.495(2) . ?
C21 C23 1.512(3) . ?
C21 C22 1.517(3) . ?
C21 C24 1.520(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
F51 C52 1.355(2) . ?
C52 C53 1.363(3) . ?
C52 C57 1.387(3) . ?
C53 C54 1.371(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.378(3) . ?
C54 H54 0.9500 . ?
C55 C56 1.380(2) . ?
C55 H55 0.9500 . ?
C56 C57 1.378(2) . ?
C56 N58 1.450(2) . ?
C57 H57 0.9500 . ?
N58 C59 1.400(2) . ?
N58 C68 1.414(2) . ?
C59 O60 1.213(2) . ?
C59 C61B 1.494(2) . ?
C59 C61A 1.494(2) . ?
C61A C66A 1.382(3) . ?
C61A C62A 1.388(3) . ?
C62A C63A 1.377(3) . ?
C62A H62A 0.9500 . ?
C63A C64A 1.386(3) . ?
C63A H63A 0.9500 . ?
C64A C65A 1.382(3) . ?
C64A H64A 0.9500 . ?
C65A C66A 1.369(3) . ?
C65A H65A 0.9500 . ?
C66A F67A 1.336(2) . ?
C61B C66B 1.382(3) . ?
C61B C62B 1.388(3) . ?
C62B F67B 1.312(6) . ?
C62B C63B 1.377(3) . ?
C63B C64B 1.386(3) . ?
C63B H63B 0.9500 . ?
C64B C65B 1.382(3) . ?
C64B H64B 0.9500 . ?
C65B C66B 1.369(3) . ?
C65B H65B 0.9500 . ?
C66B H66B 0.9500 . ?
C68 O69 1.195(2) . ?
C68 O70 1.319(2) . ?
O70 C71 1.498(2) . ?
C71 C72 1.510(3) . ?
C71 C74 1.510(3) . ?
C71 C73 1.512(3) . ?
C72 H72A 0.9800 . ?
C72 H72B 0.9800 . ?
C72 H72C 0.9800 . ?
C73 H73A 0.9800 . ?
C73 H73B 0.9800 . ?
C73 H73C 0.9800 . ?
C74 H74A 0.9800 . ?
C74 H74B 0.9800 . ?
C74 H74C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C2 C3 118.52(17) . . ?
F1 C2 C7 118.49(17) . . ?
C3 C2 C7 123.00(18) . . ?
C2 C3 C4 118.19(18) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 120.70(18) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C6 C5 C4 119.26(18) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C7 C6 C5 121.08(17) . . ?
C7 C6 N8 119.09(16) . . ?
C5 C6 N8 119.83(16) . . ?
C2 C7 C6 117.76(17) . . ?
C2 C7 H7 121.1 . . ?
C6 C7 H7 121.1 . . ?
C9 N8 C18 126.67(14) . . ?
C9 N8 C6 117.08(14) . . ?
C18 N8 C6 116.15(13) . . ?
O10 C9 N8 119.83(16) . . ?
O10 C9 C11 120.36(15) . . ?
N8 C9 C11 119.73(15) . . ?
C16 C11 C12 117.24(17) . . ?
C16 C11 C9 124.10(16) . . ?
C12 C11 C9 118.47(16) . . ?
C13 C12 C11 120.68(18) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.31(19) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.98(18) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 118.70(19) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
F17 C16 C15 118.48(17) . . ?
F17 C16 C11 118.44(16) . . ?
C15 C16 C11 123.08(18) . . ?
O19 C18 O20 128.26(16) . . ?
O19 C18 N8 121.46(16) . . ?
O20 C18 N8 110.23(14) . . ?
C18 O20 C21 121.32(13) . . ?
O20 C21 C23 101.52(13) . . ?
O20 C21 C22 110.15(14) . . ?
C23 C21 C22 111.58(17) . . ?
O20 C21 C24 109.75(14) . . ?
C23 C21 C24 111.01(15) . . ?
C22 C21 C24 112.31(16) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
F51 C52 C53 119.37(18) . . ?
F51 C52 C57 117.34(19) . . ?
C53 C52 C57 123.28(18) . . ?
C52 C53 C54 117.97(18) . . ?
C52 C53 H53 121.0 . . ?
C54 C53 H53 121.0 . . ?
C53 C54 C55 121.13(19) . . ?
C53 C54 H54 119.4 . . ?
C55 C54 H54 119.4 . . ?
C54 C55 C56 119.41(17) . . ?
C54 C55 H55 120.3 . . ?
C56 C55 H55 120.3 . . ?
C57 C56 C55 121.07(16) . . ?
C57 C56 N58 118.99(16) . . ?
C55 C56 N58 119.94(15) . . ?
C56 C57 C52 117.14(18) . . ?
C56 C57 H57 121.4 . . ?
C52 C57 H57 121.4 . . ?
C59 N58 C68 126.77(15) . . ?
C59 N58 C56 116.76(14) . . ?
C68 N58 C56 116.30(14) . . ?
O60 C59 N58 119.86(16) . . ?
O60 C59 C61B 120.60(17) . . ?
N58 C59 C61B 119.33(16) . . ?
O60 C59 C61A 120.60(17) . . ?
N58 C59 C61A 119.33(16) . . ?
C66A C61A C62A 117.32(17) . . ?
C66A C61A C59 119.56(17) . . ?
C62A C61A C59 122.73(17) . . ?
C63A C62A C61A 121.13(19) . . ?
C63A C62A H62A 119.4 . . ?
C61A C62A H62A 119.4 . . ?
C62A C63A C64A 119.6(2) . . ?
C62A C63A H63A 120.2 . . ?
C64A C63A H63A 120.2 . . ?
C65A C64A C63A 120.60(18) . . ?
C65A C64A H64A 119.7 . . ?
C63A C64A H64A 119.7 . . ?
C66A C65A C64A 118.20(19) . . ?
C66A C65A H65A 120.9 . . ?
C64A C65A H65A 120.9 . . ?
F67A C66A C65A 118.57(18) . . ?
F67A C66A C61A 118.15(17) . . ?
C65A C66A C61A 123.16(19) . . ?
C66B C61B C62B 117.32(17) . . ?
C66B C61B C59 119.56(17) . . ?
C62B C61B C59 122.73(17) . . ?
F67B C62B C63B 127.0(3) . . ?
F67B C62B C61B 111.0(3) . . ?
C63B C62B C61B 121.13(19) . . ?
C62B C63B C64B 119.6(2) . . ?
C62B C63B H63B 120.2 . . ?
C64B C63B H63B 120.2 . . ?
C65B C64B C63B 120.60(18) . . ?
C65B C64B H64B 119.7 . . ?
C63B C64B H64B 119.7 . . ?
C66B C65B C64B 118.20(19) . . ?
C66B C65B H65B 120.9 . . ?
C64B C65B H65B 120.9 . . ?
C65B C66B C61B 123.16(19) . . ?
C65B C66B H66B 118.4 . . ?
C61B C66B H66B 118.4 . . ?
O69 C68 O70 127.85(16) . . ?
O69 C68 N58 120.76(16) . . ?
O70 C68 N58 111.35(15) . . ?
C68 O70 C71 120.56(13) . . ?
O70 C71 C72 110.05(14) . . ?
O70 C71 C74 109.39(15) . . ?
C72 C71 C74 112.50(17) . . ?
O70 C71 C73 101.24(14) . . ?
C72 C71 C73 111.27(17) . . ?
C74 C71 C73 111.81(17) . . ?
C71 C72 H72A 109.5 . . ?
C71 C72 H72B 109.5 . . ?
H72A C72 H72B 109.5 . . ?
C71 C72 H72C 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 109.5 . . ?
C71 C73 H73A 109.5 . . ?
C71 C73 H73B 109.5 . . ?
H73A C73 H73B 109.5 . . ?
C71 C73 H73C 109.5 . . ?
H73A C73 H73C 109.5 . . ?
H73B C73 H73C 109.5 . . ?
C71 C74 H74A 109.5 . . ?
C71 C74 H74B 109.5 . . ?
H74A C74 H74B 109.5 . . ?
C71 C74 H74C 109.5 . . ?
H74A C74 H74C 109.5 . . ?
H74B C74 H74C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C2 C3 C4 178.36(16) . . . . ?
C7 C2 C3 C4 -1.0(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C4 C5 C6 N8 -179.82(16) . . . . ?
F1 C2 C7 C6 -177.80(15) . . . . ?
C3 C2 C7 C6 1.5(3) . . . . ?
C5 C6 C7 C2 -0.9(3) . . . . ?
N8 C6 C7 C2 178.69(15) . . . . ?
C7 C6 N8 C9 -74.0(2) . . . . ?
C5 C6 N8 C9 105.61(19) . . . . ?
C7 C6 N8 C18 109.22(18) . . . . ?
C5 C6 N8 C18 -71.2(2) . . . . ?
C18 N8 C9 O10 163.14(16) . . . . ?
C6 N8 C9 O10 -13.3(3) . . . . ?
C18 N8 C9 C11 -20.1(3) . . . . ?
C6 N8 C9 C11 163.47(15) . . . . ?
O10 C9 C11 C16 127.2(2) . . . . ?
N8 C9 C11 C16 -49.5(2) . . . . ?
O10 C9 C11 C12 -47.7(2) . . . . ?
N8 C9 C11 C12 135.60(18) . . . . ?
C16 C11 C12 C13 1.6(3) . . . . ?
C9 C11 C12 C13 176.83(16) . . . . ?
C11 C12 C13 C14 -1.3(3) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C14 C15 C16 F17 -179.54(16) . . . . ?
C14 C15 C16 C11 0.4(3) . . . . ?
C12 C11 C16 F17 178.78(15) . . . . ?
C9 C11 C16 F17 3.8(3) . . . . ?
C12 C11 C16 C15 -1.2(3) . . . . ?
C9 C11 C16 C15 -176.12(17) . . . . ?
C9 N8 C18 O19 159.70(18) . . . . ?
C6 N8 C18 O19 -23.9(2) . . . . ?
C9 N8 C18 O20 -22.5(2) . . . . ?
C6 N8 C18 O20 153.90(15) . . . . ?
O19 C18 O20 C21 -9.3(3) . . . . ?
N8 C18 O20 C21 173.10(13) . . . . ?
C18 O20 C21 C23 -176.63(15) . . . . ?
C18 O20 C21 C22 -58.3(2) . . . . ?
C18 O20 C21 C24 65.8(2) . . . . ?
F51 C52 C53 C54 178.07(18) . . . . ?
C57 C52 C53 C54 -1.1(3) . . . . ?
C52 C53 C54 C55 1.2(3) . . . . ?
C53 C54 C55 C56 -0.6(3) . . . . ?
C54 C55 C56 C57 -0.1(3) . . . . ?
C54 C55 C56 N58 179.32(17) . . . . ?
C55 C56 C57 C52 0.2(3) . . . . ?
N58 C56 C57 C52 -179.23(16) . . . . ?
F51 C52 C57 C56 -178.76(17) . . . . ?
C53 C52 C57 C56 0.4(3) . . . . ?
C57 C56 N58 C59 -106.58(19) . . . . ?
C55 C56 N58 C59 74.0(2) . . . . ?
C57 C56 N58 C68 69.0(2) . . . . ?
C55 C56 N58 C68 -110.45(19) . . . . ?
C68 N58 C59 O60 -161.30(18) . . . . ?
C56 N58 C59 O60 13.7(3) . . . . ?
C68 N58 C59 C61B 24.0(3) . . . . ?
C56 N58 C59 C61B -160.94(16) . . . . ?
C68 N58 C59 C61A 24.0(3) . . . . ?
C56 N58 C59 C61A -160.94(16) . . . . ?
O60 C59 C61A C66A 56.9(3) . . . . ?
N58 C59 C61A C66A -128.49(19) . . . . ?
O60 C59 C61A C62A -115.8(2) . . . . ?
N58 C59 C61A C62A 58.8(2) . . . . ?
C66A C61A C62A C63A 0.6(3) . . . . ?
C59 C61A C62A C63A 173.46(18) . . . . ?
C61A C62A C63A C64A 0.6(3) . . . . ?
C62A C63A C64A C65A -0.7(3) . . . . ?
C63A C64A C65A C66A -0.5(3) . . . . ?
C64A C65A C66A F67A 177.73(19) . . . . ?
C64A C65A C66A C61A 1.8(3) . . . . ?
C62A C61A C66A F67A -177.84(17) . . . . ?
C59 C61A C66A F67A 9.1(3) . . . . ?
C62A C61A C66A C65A -1.9(3) . . . . ?
C59 C61A C66A C65A -174.94(18) . . . . ?
O60 C59 C61B C66B 56.9(3) . . . . ?
N58 C59 C61B C66B -128.49(19) . . . . ?
O60 C59 C61B C62B -115.8(2) . . . . ?
N58 C59 C61B C62B 58.8(2) . . . . ?
C66B C61B C62B F67B 170.7(3) . . . . ?
C59 C61B C62B F67B -16.4(4) . . . . ?
C66B C61B C62B C63B 0.6(3) . . . . ?
C59 C61B C62B C63B 173.46(18) . . . . ?
F67B C62B C63B C64B -167.8(4) . . . . ?
C61B C62B C63B C64B 0.6(3) . . . . ?
C62B C63B C64B C65B -0.7(3) . . . . ?
C63B C64B C65B C66B -0.5(3) . . . . ?
C64B C65B C66B C61B 1.8(3) . . . . ?
C62B C61B C66B C65B -1.9(3) . . . . ?
C59 C61B C66B C65B -174.94(18) . . . . ?
C59 N58 C68 O69 -167.86(17) . . . . ?
C56 N58 C68 O69 17.1(2) . . . . ?
C59 N58 C68 O70 14.2(2) . . . . ?
C56 N58 C68 O70 -160.86(14) . . . . ?
O69 C68 O70 C71 13.7(3) . . . . ?
N58 C68 O70 C71 -168.50(14) . . . . ?
C68 O70 C71 C72 -66.4(2) . . . . ?
C68 O70 C71 C74 57.6(2) . . . . ?
C68 O70 C71 C73 175.78(16) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_NM022
_database_code_depnum_ccdc_archive 'CCDC 2204832'
loop_
_audit_author_name
_audit_author_address
'Thierry ROISNEL'
;Institut des Sciences Chimiques de Rennes
France
;
_audit_update_record             
;
2022-09-01 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 13 janvier 2021                                          #
#------------------------------------------------------------------------------#


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H14 N2 S'
_chemical_formula_sum            'C22 H14 N2 S'
_chemical_formula_weight         338.41
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
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                   13.8094(10)
_cell_length_b                   12.1986(9)
_cell_length_c                   19.1371(15)
_cell_angle_alpha                90
_cell_angle_beta                 99.043(3)
_cell_angle_gamma                90
_cell_volume                     3183.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4518
_cell_measurement_theta_min      2.2400
_cell_measurement_theta_max      25.2097
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0208013
_diffrn_orient_matrix_UB_21      -0.0595745
_diffrn_orient_matrix_UB_31      -0.0373477
_diffrn_orient_matrix_UB_12      0.0290491
_diffrn_orient_matrix_UB_22      0.0477419
_diffrn_orient_matrix_UB_32      -0.0599755
_diffrn_orient_matrix_UB_13      0.0489202
_diffrn_orient_matrix_UB_23      -0.0053427
_diffrn_orient_matrix_UB_33      0.0194416


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

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.120
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1408
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_T_max  0.975

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

# Software                   : BIS 2014.5.0.0/23-May-2014 && APEX2_2014.11-0   #
# Number of scans            :        3                                        #
# Total number of frames     :      282                                        #
# Total length of scans      :   282.00 (deg.)                                 #
# Rotation speed             :    20.00 sec./deg.                              #
# Total exposition time      :      1 h  34.0 min.                             #
#                                                                              #
#    Scan  Time(s)  Width  DX (mm)  Frames  Theta  Omega    Phi    Chi   T(K)  #
#..............................................................................#
#                                                                              #
#  1 Omega    20.0   1.00     35.0      93 343.95 342.08 358.37 334.29 149.99  #
#  2 Omega    20.0   1.00     35.0      93 343.95 342.07 248.78 334.30 150.01  #
#  3 Omega    20.0   1.00     35.0      96 347.19 343.89  95.65 330.64 150.01  #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.33
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_uneti/neti     0.0630
_diffrn_reflns_av_r_equivalents  0.0408
_diffrn_reflns_number            21613
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.240
_diffrn_reflns_theta_max         27.521
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             7274
_reflns_number_gt                4807
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

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

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'

#------------------------------------------------------------------------------#
#                            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     
'w=1/[σ²(Fo²)+(0.0470P)²+0.5384P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7274
_refine_ls_number_parameters     453
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1140
_refine_ls_wR_factor_gt          0.0990
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.055

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.15016(4) 0.68970(5) 0.71201(3) 0.03807(17) Uani 1 1 d . . . . .
C1 C 0.31667(17) 0.4090(2) 0.91546(12) 0.0437(6) Uani 1 1 d . . . . .
H1A H 0.374912 0.456057 0.920989 0.066 Uiso 1 1 calc R U . . .
H1B H 0.336834 0.331969 0.916075 0.066 Uiso 1 1 calc R U . . .
H1C H 0.279902 0.422625 0.954426 0.066 Uiso 1 1 calc R U . . .
N2 N 0.25519(12) 0.43332(14) 0.84886(9) 0.0279(4) Uani 1 1 d . . . . .
C3 C 0.28139(14) 0.41914(16) 0.78233(11) 0.0241(5) Uani 1 1 d . . . . .
C4 C 0.36851(14) 0.37812(16) 0.76542(12) 0.0305(5) Uani 1 1 d . . . . .
H4 H 0.418792 0.351798 0.801109 0.037 Uiso 1 1 calc R U . . .
C5 C 0.37967(15) 0.37684(16) 0.69503(13) 0.0311(5) Uani 1 1 d . . . . .
H5 H 0.438129 0.347833 0.681994 0.037 Uiso 1 1 calc R U . . .
C6 C 0.30702(14) 0.41719(17) 0.64284(12) 0.0291(5) Uani 1 1 d . . . . .
H6 H 0.317525 0.418099 0.594961 0.035 Uiso 1 1 calc R U . . .
C7 C 0.21956(14) 0.45604(16) 0.65990(11) 0.0240(5) Uani 1 1 d . . . . .
H7 H 0.170223 0.483321 0.623883 0.029 Uiso 1 1 calc R U . . .
C8 C 0.20409(13) 0.45499(15) 0.73018(11) 0.0217(4) Uani 1 1 d . . . . .
C9 C 0.12575(14) 0.49179(15) 0.76779(10) 0.0215(4) Uani 1 1 d . . . . .
C10 C 0.16399(14) 0.48068(16) 0.84165(11) 0.0246(5) Uani 1 1 d . . . . .
N11 N 0.12160(13) 0.50765(14) 0.89594(9) 0.0302(4) Uani 1 1 d . . . . .
C12 C 0.03409(15) 0.56169(17) 0.87860(11) 0.0290(5) Uani 1 1 d . . . . .
C13 C -0.01055(18) 0.60245(18) 0.93487(13) 0.0389(6) Uani 1 1 d . . . . .
H13 H 0.019555 0.590331 0.982384 0.047 Uiso 1 1 calc R U . . .
C14 C -0.09658(19) 0.6591(2) 0.92141(15) 0.0457(7) Uani 1 1 d . . . . .
H14 H -0.126520 0.684392 0.959827 0.055 Uiso 1 1 calc R U . . .
C15 C -0.14155(17) 0.68053(18) 0.85212(14) 0.0396(6) Uani 1 1 d . . . . .
H15 H -0.201131 0.720792 0.843642 0.048 Uiso 1 1 calc R U . . .
C16 C -0.09896(15) 0.64295(17) 0.79611(12) 0.0305(5) Uani 1 1 d . . . . .
C17 C -0.01161(14) 0.57898(16) 0.80723(11) 0.0248(5) Uani 1 1 d . . . . .
C18 C 0.03152(13) 0.53335(15) 0.75040(11) 0.0213(4) Uani 1 1 d . . . . .
C21 C -0.02666(13) 0.52524(16) 0.67906(11) 0.0231(5) Uani 1 1 d . . . . .
C22 C -0.00781(14) 0.44174(17) 0.63300(11) 0.0253(5) Uani 1 1 d . . . . .
H22 H 0.041811 0.389447 0.648762 0.030 Uiso 1 1 calc R U . . .
C23 C -0.05933(15) 0.4330(2) 0.56516(11) 0.0343(5) Uani 1 1 d . . . . .
H23 H -0.044076 0.376513 0.534518 0.041 Uiso 1 1 calc R U . . .
C24 C -0.13338(16) 0.5075(2) 0.54220(12) 0.0424(6) Uani 1 1 d . . . . .
H24 H -0.167268 0.504091 0.495041 0.051 Uiso 1 1 calc R U . . .
C25 C -0.15762(15) 0.5860(2) 0.58782(13) 0.0398(6) Uani 1 1 d . . . . .
H25 H -0.209649 0.635565 0.572261 0.048 Uiso 1 1 calc R U . . .
C26 C -0.10694(14) 0.59424(17) 0.65670(12) 0.0293(5) Uani 1 1 d . . . . .
S2 S 0.62138(4) 0.49010(4) 0.66842(3) 0.02816(14) Uani 1 1 d . . . . .
C51 C 0.24125(15) 0.75374(18) 0.87675(11) 0.0331(5) Uani 1 1 d . . . . .
H51A H 0.231180 0.832850 0.880886 0.050 Uiso 1 1 calc R U . . .
H51B H 0.292098 0.729271 0.915167 0.050 Uiso 1 1 calc R U . . .
H51C H 0.179837 0.715120 0.879817 0.050 Uiso 1 1 calc R U . . .
N52 N 0.27172(11) 0.73010(13) 0.80942(9) 0.0240(4) Uani 1 1 d . . . . .
C53 C 0.21842(14) 0.74934(15) 0.74312(11) 0.0240(5) Uani 1 1 d . . . . .
C54 C 0.12301(14) 0.78888(16) 0.72693(13) 0.0312(5) Uani 1 1 d . . . . .
H54 H 0.087030 0.809881 0.763188 0.037 Uiso 1 1 calc R U . . .
C55 C 0.08241(15) 0.79658(17) 0.65649(13) 0.0339(6) Uani 1 1 d . . . . .
H55 H 0.017893 0.824796 0.643973 0.041 Uiso 1 1 calc R U . . .
C56 C 0.13440(15) 0.76372(17) 0.60358(12) 0.0342(6) Uani 1 1 d . . . . .
H56 H 0.104156 0.767898 0.555505 0.041 Uiso 1 1 calc R U . . .
C57 C 0.22948(14) 0.72501(16) 0.61969(11) 0.0269(5) Uani 1 1 d . . . . .
H57 H 0.264066 0.702232 0.583045 0.032 Uiso 1 1 calc R U . . .
C58 C 0.27402(14) 0.71977(15) 0.69020(11) 0.0220(4) Uani 1 1 d . . . . .
C59 C 0.36853(13) 0.68127(15) 0.72740(10) 0.0196(4) Uani 1 1 d . . . . .
C60 C 0.36109(13) 0.68650(15) 0.80127(11) 0.0209(4) Uani 1 1 d . . . . .
N61 N 0.42708(11) 0.65757(13) 0.85531(8) 0.0236(4) Uani 1 1 d . . . . .
C62 C 0.50921(13) 0.60893(15) 0.83725(10) 0.0212(4) Uani 1 1 d . . . . .
C63 C 0.57998(14) 0.56907(16) 0.89263(11) 0.0267(5) Uani 1 1 d . . . . .
H63 H 0.570237 0.578661 0.940299 0.032 Uiso 1 1 calc R U . . .
C64 C 0.66218(15) 0.51696(17) 0.87869(11) 0.0297(5) Uani 1 1 d . . . . .
H64 H 0.710219 0.492968 0.916671 0.036 Uiso 1 1 calc R U . . .
C65 C 0.67628(14) 0.49855(16) 0.80869(11) 0.0265(5) Uani 1 1 d . . . . .
H65 H 0.732902 0.460518 0.799357 0.032 Uiso 1 1 calc R U . . .
C66 C 0.60822(13) 0.53552(15) 0.75360(11) 0.0223(4) Uani 1 1 d . . . . .
C67 C 0.52433(13) 0.59630(15) 0.76572(10) 0.0195(4) Uani 1 1 d . . . . .
C68 C 0.45618(13) 0.64311(15) 0.70958(10) 0.0189(4) Uani 1 1 d . . . . .
C69 C 0.48335(13) 0.65493(16) 0.63871(10) 0.0207(4) Uani 1 1 d . . . . .
C70 C 0.44452(14) 0.74084(16) 0.59399(10) 0.0249(5) Uani 1 1 d . . . . .
H70 H 0.403312 0.793409 0.611212 0.030 Uiso 1 1 calc R U . . .
C71 C 0.46428(15) 0.75121(18) 0.52610(11) 0.0297(5) Uani 1 1 d . . . . .
H71 H 0.436145 0.809628 0.496907 0.036 Uiso 1 1 calc R U . . .
C72 C 0.52540(15) 0.67616(19) 0.50030(12) 0.0327(5) Uani 1 1 d . . . . .
H72 H 0.535401 0.679604 0.452360 0.039 Uiso 1 1 calc R U . . .
C73 C 0.57159(14) 0.59645(18) 0.54476(11) 0.0284(5) Uani 1 1 d . . . . .
H73 H 0.616306 0.547530 0.528007 0.034 Uiso 1 1 calc R U . . .
C74 C 0.55313(14) 0.58722(16) 0.61400(11) 0.0235(5) 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
S1 C26 1.741(2) . ?
S1 C16 1.749(2) . ?
C1 N2 1.447(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N2 C10 1.373(3) . ?
N2 C3 1.388(3) . ?
C3 C4 1.387(3) . ?
C3 C8 1.411(3) . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.395(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.461(3) . ?
C9 C18 1.388(3) . ?
C9 C10 1.435(3) . ?
C10 N11 1.312(3) . ?
N11 C12 1.371(3) . ?
C12 C13 1.413(3) . ?
C12 C17 1.427(3) . ?
C13 C14 1.363(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.398(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.424(3) . ?
C17 C18 1.432(3) . ?
C18 C21 1.475(3) . ?
C21 C22 1.398(3) . ?
C21 C26 1.404(3) . ?
C22 C23 1.383(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.386(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.373(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.395(3) . ?
C25 H25 0.9500 . ?
S2 C74 1.752(2) . ?
S2 C66 1.758(2) . ?
C51 N52 1.446(2) . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
N52 C60 1.375(2) . ?
N52 C53 1.383(2) . ?
C53 C54 1.391(3) . ?
C53 C58 1.411(3) . ?
C54 C55 1.379(3) . ?
C54 H54 0.9500 . ?
C55 C56 1.389(3) . ?
C55 H55 0.9500 . ?
C56 C57 1.384(3) . ?
C56 H56 0.9500 . ?
C57 C58 1.394(3) . ?
C57 H57 0.9500 . ?
C58 C59 1.462(2) . ?
C59 C68 1.388(3) . ?
C59 C60 1.435(3) . ?
C60 N61 1.315(2) . ?
N61 C62 1.372(2) . ?
C62 C63 1.410(3) . ?
C62 C67 1.425(3) . ?
C63 C64 1.364(3) . ?
C63 H63 0.9500 . ?
C64 C65 1.402(3) . ?
C64 H64 0.9500 . ?
C65 C66 1.374(3) . ?
C65 H65 0.9500 . ?
C66 C67 1.425(3) . ?
C67 C68 1.431(2) . ?
C68 C69 1.470(3) . ?
C69 C70 1.405(3) . ?
C69 C74 1.406(3) . ?
C70 C71 1.375(3) . ?
C70 H70 0.9500 . ?
C71 C72 1.388(3) . ?
C71 H71 0.9500 . ?
C72 C73 1.380(3) . ?
C72 H72 0.9500 . ?
C73 C74 1.393(3) . ?
C73 H73 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
C26 S1 C16 102.35(10) . . ?
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C10 N2 C3 109.12(16) . . ?
C10 N2 C1 125.22(19) . . ?
C3 N2 C1 125.53(18) . . ?
C4 C3 N2 128.27(19) . . ?
C4 C3 C8 122.3(2) . . ?
N2 C3 C8 109.44(17) . . ?
C5 C4 C3 117.75(19) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
C4 C5 C6 121.26(19) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 119.75(19) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C8 C3 118.12(18) . . ?
C7 C8 C9 135.22(18) . . ?
C3 C8 C9 106.45(18) . . ?
C18 C9 C10 117.17(18) . . ?
C18 C9 C8 137.16(18) . . ?
C10 C9 C8 105.65(16) . . ?
N11 C10 N2 122.85(18) . . ?
N11 C10 C9 127.96(19) . . ?
N2 C10 C9 109.17(18) . . ?
C10 N11 C12 114.52(18) . . ?
N11 C12 C13 117.3(2) . . ?
N11 C12 C17 122.89(19) . . ?
C13 C12 C17 119.8(2) . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 121.2(2) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 121.4(2) . . ?
C15 C16 S1 116.53(17) . . ?
C17 C16 S1 121.78(16) . . ?
C16 C17 C12 117.42(19) . . ?
C16 C17 C18 122.89(19) . . ?
C12 C17 C18 119.68(18) . . ?
C9 C18 C17 116.50(18) . . ?
C9 C18 C21 123.47(18) . . ?
C17 C18 C21 119.88(17) . . ?
C22 C21 C26 117.45(19) . . ?
C22 C21 C18 120.29(17) . . ?
C26 C21 C18 122.08(19) . . ?
C23 C22 C21 121.9(2) . . ?
C23 C22 H22 119.0 . . ?
C21 C22 H22 119.0 . . ?
C22 C23 C24 119.5(2) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C25 C24 C23 119.8(2) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 121.0(2) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C25 C26 C21 120.0(2) . . ?
C25 C26 S1 116.96(16) . . ?
C21 C26 S1 123.05(17) . . ?
C74 S2 C66 102.35(9) . . ?
N52 C51 H51A 109.5 . . ?
N52 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
N52 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C60 N52 C53 108.61(16) . . ?
C60 N52 C51 124.77(17) . . ?
C53 N52 C51 126.60(17) . . ?
N52 C53 C54 127.72(19) . . ?
N52 C53 C58 110.12(17) . . ?
C54 C53 C58 122.14(19) . . ?
C55 C54 C53 117.8(2) . . ?
C55 C54 H54 121.1 . . ?
C53 C54 H54 121.1 . . ?
C54 C55 C56 121.02(19) . . ?
C54 C55 H55 119.5 . . ?
C56 C55 H55 119.5 . . ?
C57 C56 C55 121.1(2) . . ?
C57 C56 H56 119.4 . . ?
C55 C56 H56 119.4 . . ?
C56 C57 C58 119.4(2) . . ?
C56 C57 H57 120.3 . . ?
C58 C57 H57 120.3 . . ?
C57 C58 C53 118.44(18) . . ?
C57 C58 C59 135.26(19) . . ?
C53 C58 C59 106.11(17) . . ?
C68 C59 C60 117.20(17) . . ?
C68 C59 C58 137.21(19) . . ?
C60 C59 C58 105.59(16) . . ?
N61 C60 N52 122.55(18) . . ?
N61 C60 C59 127.96(17) . . ?
N52 C60 C59 109.48(16) . . ?
C60 N61 C62 114.60(17) . . ?
N61 C62 C63 117.55(18) . . ?
N61 C62 C67 122.73(17) . . ?
C63 C62 C67 119.71(18) . . ?
C64 C63 C62 120.9(2) . . ?
C64 C63 H63 119.5 . . ?
C62 C63 H63 119.5 . . ?
C63 C64 C65 120.44(19) . . ?
C63 C64 H64 119.8 . . ?
C65 C64 H64 119.8 . . ?
C66 C65 C64 119.99(19) . . ?
C66 C65 H65 120.0 . . ?
C64 C65 H65 120.0 . . ?
C65 C66 C67 121.44(19) . . ?
C65 C66 S2 116.76(15) . . ?
C67 C66 S2 121.34(15) . . ?
C66 C67 C62 117.27(17) . . ?
C66 C67 C68 122.75(18) . . ?
C62 C67 C68 119.97(17) . . ?
C59 C68 C67 116.44(18) . . ?
C59 C68 C69 123.54(17) . . ?
C67 C68 C69 119.90(16) . . ?
C70 C69 C74 116.70(18) . . ?
C70 C69 C68 120.45(17) . . ?
C74 C69 C68 122.72(18) . . ?
C71 C70 C69 122.06(19) . . ?
C71 C70 H70 119.0 . . ?
C69 C70 H70 119.0 . . ?
C70 C71 C72 119.8(2) . . ?
C70 C71 H71 120.1 . . ?
C72 C71 H71 120.1 . . ?
C73 C72 C71 119.6(2) . . ?
C73 C72 H72 120.2 . . ?
C71 C72 H72 120.2 . . ?
C72 C73 C74 120.5(2) . . ?
C72 C73 H73 119.8 . . ?
C74 C73 H73 119.8 . . ?
C73 C74 C69 120.67(19) . . ?
C73 C74 S2 117.29(15) . . ?
C69 C74 S2 122.03(16) . . ?

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
C10 N2 C3 C4 177.42(19) . . . . ?
C1 N2 C3 C4 1.3(3) . . . . ?
C10 N2 C3 C8 -1.9(2) . . . . ?
C1 N2 C3 C8 -178.02(18) . . . . ?
N2 C3 C4 C5 -176.81(19) . . . . ?
C8 C3 C4 C5 2.4(3) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C4 C5 C6 C7 -2.5(3) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 C3 3.3(3) . . . . ?
C6 C7 C8 C9 177.1(2) . . . . ?
C4 C3 C8 C7 -4.6(3) . . . . ?
N2 C3 C8 C7 174.68(16) . . . . ?
C4 C3 C8 C9 179.88(18) . . . . ?
N2 C3 C8 C9 -0.8(2) . . . . ?
C7 C8 C9 C18 7.3(4) . . . . ?
C3 C8 C9 C18 -178.4(2) . . . . ?
C7 C8 C9 C10 -171.3(2) . . . . ?
C3 C8 C9 C10 3.0(2) . . . . ?
C3 N2 C10 N11 -177.43(17) . . . . ?
C1 N2 C10 N11 -1.3(3) . . . . ?
C3 N2 C10 C9 3.8(2) . . . . ?
C1 N2 C10 C9 179.99(18) . . . . ?
C18 C9 C10 N11 -1.8(3) . . . . ?
C8 C9 C10 N11 177.13(19) . . . . ?
C18 C9 C10 N2 176.85(16) . . . . ?
C8 C9 C10 N2 -4.2(2) . . . . ?
N2 C10 N11 C12 175.18(18) . . . . ?
C9 C10 N11 C12 -6.3(3) . . . . ?
C10 N11 C12 C13 -173.96(18) . . . . ?
C10 N11 C12 C17 5.2(3) . . . . ?
N11 C12 C13 C14 178.6(2) . . . . ?
C17 C12 C13 C14 -0.6(3) . . . . ?
C12 C13 C14 C15 -1.5(3) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
C14 C15 C16 C17 2.3(3) . . . . ?
C14 C15 C16 S1 -171.20(17) . . . . ?
C26 S1 C16 C15 -161.30(16) . . . . ?
C26 S1 C16 C17 25.20(19) . . . . ?
C15 C16 C17 C12 -4.3(3) . . . . ?
S1 C16 C17 C12 168.88(15) . . . . ?
C15 C16 C17 C18 176.32(19) . . . . ?
S1 C16 C17 C18 -10.5(3) . . . . ?
N11 C12 C17 C16 -175.71(18) . . . . ?
C13 C12 C17 C16 3.4(3) . . . . ?
N11 C12 C17 C18 3.7(3) . . . . ?
C13 C12 C17 C18 -177.21(18) . . . . ?
C10 C9 C18 C17 10.7(3) . . . . ?
C8 C9 C18 C17 -167.8(2) . . . . ?
C10 C9 C18 C21 -164.78(17) . . . . ?
C8 C9 C18 C21 16.7(3) . . . . ?
C16 C17 C18 C9 167.66(18) . . . . ?
C12 C17 C18 C9 -11.7(3) . . . . ?
C16 C17 C18 C21 -16.7(3) . . . . ?
C12 C17 C18 C21 163.95(17) . . . . ?
C9 C18 C21 C22 24.8(3) . . . . ?
C17 C18 C21 C22 -150.49(18) . . . . ?
C9 C18 C21 C26 -160.22(19) . . . . ?
C17 C18 C21 C26 24.5(3) . . . . ?
C26 C21 C22 C23 6.3(3) . . . . ?
C18 C21 C22 C23 -178.48(18) . . . . ?
C21 C22 C23 C24 -1.4(3) . . . . ?
C22 C23 C24 C25 -2.7(3) . . . . ?
C23 C24 C25 C26 1.8(3) . . . . ?
C24 C25 C26 C21 3.3(3) . . . . ?
C24 C25 C26 S1 -175.06(18) . . . . ?
C22 C21 C26 C25 -7.2(3) . . . . ?
C18 C21 C26 C25 177.73(19) . . . . ?
C22 C21 C26 S1 171.09(15) . . . . ?
C18 C21 C26 S1 -4.0(3) . . . . ?
C16 S1 C26 C25 160.21(17) . . . . ?
C16 S1 C26 C21 -18.11(19) . . . . ?
C60 N52 C53 C54 177.29(19) . . . . ?
C51 N52 C53 C54 -4.2(3) . . . . ?
C60 N52 C53 C58 -1.0(2) . . . . ?
C51 N52 C53 C58 177.51(18) . . . . ?
N52 C53 C54 C55 -176.80(19) . . . . ?
C58 C53 C54 C55 1.3(3) . . . . ?
C53 C54 C55 C56 1.3(3) . . . . ?
C54 C55 C56 C57 -1.8(3) . . . . ?
C55 C56 C57 C58 -0.5(3) . . . . ?
C56 C57 C58 C53 3.1(3) . . . . ?
C56 C57 C58 C59 177.3(2) . . . . ?
N52 C53 C58 C57 174.89(17) . . . . ?
C54 C53 C58 C57 -3.5(3) . . . . ?
N52 C53 C58 C59 -0.9(2) . . . . ?
C54 C53 C58 C59 -179.29(17) . . . . ?
C57 C58 C59 C68 6.9(4) . . . . ?
C53 C58 C59 C68 -178.4(2) . . . . ?
C57 C58 C59 C60 -172.4(2) . . . . ?
C53 C58 C59 C60 2.3(2) . . . . ?
C53 N52 C60 N61 -178.58(18) . . . . ?
C51 N52 C60 N61 2.9(3) . . . . ?
C53 N52 C60 C59 2.6(2) . . . . ?
C51 N52 C60 C59 -176.02(17) . . . . ?
C68 C59 C60 N61 -1.3(3) . . . . ?
C58 C59 C60 N61 178.19(19) . . . . ?
C68 C59 C60 N52 177.50(16) . . . . ?
C58 C59 C60 N52 -3.0(2) . . . . ?
N52 C60 N61 C62 175.88(17) . . . . ?
C59 C60 N61 C62 -5.5(3) . . . . ?
C60 N61 C62 C63 -175.76(17) . . . . ?
C60 N61 C62 C67 3.4(3) . . . . ?
N61 C62 C63 C64 178.12(18) . . . . ?
C67 C62 C63 C64 -1.0(3) . . . . ?
C62 C63 C64 C65 -2.3(3) . . . . ?
C63 C64 C65 C66 1.6(3) . . . . ?
C64 C65 C66 C67 2.3(3) . . . . ?
C64 C65 C66 S2 -170.06(15) . . . . ?
C74 S2 C66 C65 -160.36(15) . . . . ?
C74 S2 C66 C67 27.26(18) . . . . ?
C65 C66 C67 C62 -5.4(3) . . . . ?
S2 C66 C67 C62 166.61(14) . . . . ?
C65 C66 C67 C68 175.06(18) . . . . ?
S2 C66 C67 C68 -12.9(3) . . . . ?
N61 C62 C67 C66 -174.37(17) . . . . ?
C63 C62 C67 C66 4.7(3) . . . . ?
N61 C62 C67 C68 5.2(3) . . . . ?
C63 C62 C67 C68 -175.74(17) . . . . ?
C60 C59 C68 C67 9.8(2) . . . . ?
C58 C59 C68 C67 -169.5(2) . . . . ?
C60 C59 C68 C69 -166.31(17) . . . . ?
C58 C59 C68 C69 14.4(3) . . . . ?
C66 C67 C68 C59 167.81(17) . . . . ?
C62 C67 C68 C59 -11.7(3) . . . . ?
C66 C67 C68 C69 -16.0(3) . . . . ?
C62 C67 C68 C69 164.52(16) . . . . ?
C59 C68 C69 C70 26.2(3) . . . . ?
C67 C68 C69 C70 -149.70(18) . . . . ?
C59 C68 C69 C74 -158.12(18) . . . . ?
C67 C68 C69 C74 25.9(3) . . . . ?
C74 C69 C70 C71 7.5(3) . . . . ?
C68 C69 C70 C71 -176.60(17) . . . . ?
C69 C70 C71 C72 -0.9(3) . . . . ?
C70 C71 C72 C73 -4.7(3) . . . . ?
C71 C72 C73 C74 3.5(3) . . . . ?
C72 C73 C74 C69 3.4(3) . . . . ?
C72 C73 C74 S2 -175.64(16) . . . . ?
C70 C69 C74 C73 -8.7(3) . . . . ?
C68 C69 C74 C73 175.53(17) . . . . ?
C70 C69 C74 S2 170.32(14) . . . . ?
C68 C69 C74 S2 -5.5(3) . . . . ?
C66 S2 C74 C73 160.78(15) . . . . ?
C66 S2 C74 C69 -18.25(18) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_NM013_3
_database_code_depnum_ccdc_archive 'CCDC 2204834'
loop_
_audit_author_name
_audit_author_address
'Thierry ROISNEL'
;Institut des Sciences Chimiques de Rennes
France
;
_audit_update_record             
;
2022-09-01 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 06 avril 2021                                            #
#------------------------------------------------------------------------------#


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C21 H11 N O3 S), C H2 Cl2'
_chemical_formula_sum            'C43 H24 Cl2 N2 O6 S2'
_chemical_formula_weight         799.66
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#


_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2771(3)
_cell_length_b                   13.4367(6)
_cell_length_c                   15.9360(6)
_cell_angle_alpha                95.3390(10)
_cell_angle_beta                 93.9650(10)
_cell_angle_gamma                99.893(2)
_cell_volume                     1731.86(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5485
_cell_measurement_theta_min      2.5073
_cell_measurement_theta_max      27.1283
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0841156
_diffrn_orient_matrix_UB_21      0.0269212
_diffrn_orient_matrix_UB_31      -0.0857560
_diffrn_orient_matrix_UB_12      0.0472093
_diffrn_orient_matrix_UB_22      0.0436842
_diffrn_orient_matrix_UB_32      0.0404478
_diffrn_orient_matrix_UB_13      0.0396975
_diffrn_orient_matrix_UB_23      -0.0464172
_diffrn_orient_matrix_UB_33      0.0164851


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

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.080
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             820
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  0.971

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

# Software                   : BIS 2014.5.0.0/23-May-2014 && APEX2_2014.11-0   #
# Number of scans            :        4                                        #
# Total number of frames     :      420                                        #
# Total length of scans      :   420.00 (deg.)                                 #
# Rotation speed             :   100.00 sec./deg.                              #
# Total exposition time      :     11 h  40.0 min.                             #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range  Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Omega  100.0  1.00    35.0   105  105.0   14.9   14.5    0.0  305.3 150.0 #
#  2 Omega  100.0  1.00    35.0   105  105.0   14.9   14.5  240.0  305.3 150.0 #
#  3 Omega  100.0  1.00    35.0   105  105.0   14.9   14.5  120.0  305.3 150.0 #
#  4 Omega  100.0  1.00    35.0   105  105.0   14.9   14.5   60.0  305.3 150.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.33
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_uneti/neti     0.0462
_diffrn_reflns_av_r_equivalents  0.0251
_diffrn_reflns_number            17614
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.507
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.983
_reflns_number_total             7818
_reflns_number_gt                5578
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

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

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'

#------------------------------------------------------------------------------#
#                            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     
'w=1/[σ²(Fo²)+(0.0852P)²+2.2209P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7818
_refine_ls_number_parameters     500
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1717
_refine_ls_wR_factor_gt          0.1502
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.162
_refine_diff_density_min         -1.186
_refine_diff_density_rms         0.075

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 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'
S S 0.1246 0.1234 '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'

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
S1 S -0.00399(9) 0.74186(6) 0.87620(5) 0.02823(19) Uani 1 1 d . . . . .
C1 C 0.0469(3) 0.6456(2) 0.80769(18) 0.0250(6) Uani 1 1 d . . . . .
C2 C -0.0521(4) 0.5500(2) 0.8054(2) 0.0323(7) Uani 1 1 d . . . . .
H2 H -0.141290 0.540749 0.840033 0.039 Uiso 1 1 calc R U . . .
C3 C -0.0215(4) 0.4695(3) 0.7535(2) 0.0386(8) Uani 1 1 d . . . . .
H3 H -0.089188 0.404667 0.752588 0.046 Uiso 1 1 calc R U . . .
C4 C 0.1091(4) 0.4822(2) 0.7015(2) 0.0361(7) Uani 1 1 d . . . . .
H4 H 0.131320 0.426186 0.666102 0.043 Uiso 1 1 calc R U . . .
C5 C 0.2050(4) 0.5774(2) 0.70273(18) 0.0293(6) Uani 1 1 d . . . . .
H5 H 0.292132 0.586635 0.666840 0.035 Uiso 1 1 calc R U . . .
C6 C 0.1762(3) 0.6607(2) 0.75584(17) 0.0229(6) Uani 1 1 d . . . . .
C7 C 0.2856(3) 0.7594(2) 0.75237(17) 0.0235(6) Uani 1 1 d . . . . .
O8 O 0.3807(3) 0.76768(16) 0.69672(13) 0.0355(5) Uani 1 1 d . . . . .
C9 C 0.2812(3) 0.8458(2) 0.81747(16) 0.0198(5) Uani 1 1 d . . . . .
C10 C 0.4028(3) 0.9354(2) 0.82574(16) 0.0202(5) Uani 1 1 d . . . . .
C11 C 0.4079(3) 1.0124(2) 0.88964(17) 0.0251(6) Uani 1 1 d . . . . .
H11 H 0.492739 1.070575 0.894472 0.030 Uiso 1 1 calc R U . . .
C12 C 0.2882(4) 1.0050(2) 0.94737(18) 0.0279(6) Uani 1 1 d . . . . .
H12 H 0.292460 1.057476 0.992136 0.033 Uiso 1 1 calc R U . . .
C13 C 0.1647(3) 0.9219(2) 0.93940(17) 0.0250(6) Uani 1 1 d . . . . .
H13 H 0.081084 0.918324 0.977535 0.030 Uiso 1 1 calc R U . . .
C14 C 0.1601(3) 0.8419(2) 0.87541(17) 0.0214(5) Uani 1 1 d . . . . .
N25 N 0.5276(3) 0.94848(17) 0.76813(13) 0.0213(5) Uani 1 1 d . . . . .
C26 C 0.6888(3) 0.9345(2) 0.78749(17) 0.0217(5) Uani 1 1 d . . . . .
C27 C 0.7659(3) 0.9351(2) 0.70590(17) 0.0211(5) Uani 1 1 d . . . . .
C28 C 0.9225(3) 0.9206(2) 0.68875(18) 0.0256(6) Uani 1 1 d . . . . .
H28 H 1.001862 0.912806 0.732491 0.031 Uiso 1 1 calc R U . . .
C29 C 0.9584(3) 0.9179(2) 0.60462(19) 0.0293(6) Uani 1 1 d . . . . .
H29 H 1.064375 0.907822 0.590358 0.035 Uiso 1 1 calc R U . . .
C30 C 0.8415(3) 0.9299(2) 0.54111(18) 0.0280(6) Uani 1 1 d . . . . .
H30 H 0.868720 0.926373 0.484096 0.034 Uiso 1 1 calc R U . . .
C31 C 0.6861(3) 0.9467(2) 0.55900(17) 0.0255(6) Uani 1 1 d . . . . .
H31 H 0.607386 0.956523 0.515700 0.031 Uiso 1 1 calc R U . . .
C32 C 0.6509(3) 0.9486(2) 0.64274(17) 0.0213(5) Uani 1 1 d . . . . .
C33 C 0.4961(3) 0.9599(2) 0.68159(17) 0.0227(6) Uani 1 1 d . . . . .
O34 O 0.7484(2) 0.92367(16) 0.85660(12) 0.0287(5) Uani 1 1 d . . . . .
O35 O 0.3697(2) 0.97880(16) 0.65040(12) 0.0297(5) Uani 1 1 d . . . . .
S2 S 0.84335(9) 0.57459(6) 0.03519(5) 0.02879(19) Uani 1 1 d . . . . .
C51 C 0.6935(3) 0.4730(2) 0.05396(18) 0.0246(6) Uani 1 1 d . . . . .
C52 C 0.6896(4) 0.3823(2) 0.00307(19) 0.0304(6) Uani 1 1 d . . . . .
H52 H 0.763404 0.379201 -0.039804 0.036 Uiso 1 1 calc R U . . .
C53 C 0.5785(4) 0.2970(2) 0.0152(2) 0.0331(7) Uani 1 1 d . . . . .
H53 H 0.575302 0.235321 -0.019732 0.040 Uiso 1 1 calc R U . . .
C54 C 0.4706(4) 0.3009(2) 0.0786(2) 0.0315(7) Uani 1 1 d . . . . .
H54 H 0.396030 0.241656 0.087819 0.038 Uiso 1 1 calc R U . . .
C55 C 0.4729(3) 0.3912(2) 0.12745(19) 0.0274(6) Uani 1 1 d . . . . .
H55 H 0.398544 0.393512 0.170094 0.033 Uiso 1 1 calc R U . . .
C56 C 0.5823(3) 0.4797(2) 0.11591(18) 0.0246(6) Uani 1 1 d . . . . .
C57 C 0.5685(3) 0.5747(2) 0.1681(2) 0.0289(6) Uani 1 1 d . . . . .
O58 O 0.4557(3) 0.57378(17) 0.21387(18) 0.0503(7) Uani 1 1 d . . . . .
C59 C 0.6910(3) 0.6690(2) 0.16379(18) 0.0238(6) Uani 1 1 d . . . . .
C60 C 0.6891(3) 0.7590(2) 0.21733(18) 0.0231(6) Uani 1 1 d . . . . .
C61 C 0.8055(3) 0.8455(2) 0.21696(18) 0.0268(6) Uani 1 1 d . . . . .
H61 H 0.800748 0.904554 0.253700 0.032 Uiso 1 1 calc R U . . .
C62 C 0.9304(3) 0.8461(2) 0.16253(19) 0.0279(6) Uani 1 1 d . . . . .
H62 H 1.011423 0.905469 0.162605 0.034 Uiso 1 1 calc R U . . .
C63 C 0.9367(3) 0.7614(2) 0.10907(18) 0.0259(6) Uani 1 1 d . . . . .
H63 H 1.022006 0.762011 0.072077 0.031 Uiso 1 1 calc R U . . .
C64 C 0.8167(3) 0.6733(2) 0.10885(17) 0.0233(6) Uani 1 1 d . . . . .
N65 N 0.5679(3) 0.76429(18) 0.27664(15) 0.0241(5) Uani 1 1 d . . . . .
C66 C 0.4062(3) 0.7767(2) 0.25644(19) 0.0256(6) Uani 1 1 d . . . . .
C67 C 0.3245(3) 0.7704(2) 0.33653(18) 0.0235(6) Uani 1 1 d . . . . .
C68 C 0.1651(3) 0.7775(2) 0.35301(19) 0.0283(6) Uani 1 1 d . . . . .
H68 H 0.087897 0.789901 0.310018 0.034 Uiso 1 1 calc R U . . .
C69 C 0.1215(4) 0.7660(2) 0.4347(2) 0.0328(7) Uani 1 1 d . . . . .
H69 H 0.012472 0.770133 0.447881 0.039 Uiso 1 1 calc R U . . .
C70 C 0.2354(4) 0.7485(3) 0.4973(2) 0.0377(8) Uani 1 1 d . . . . .
H70 H 0.202852 0.741151 0.552703 0.045 Uiso 1 1 calc R U . . .
C71 C 0.3959(4) 0.7415(3) 0.48071(19) 0.0355(7) Uani 1 1 d . . . . .
H71 H 0.473840 0.729718 0.523617 0.043 Uiso 1 1 calc R U . . .
C72 C 0.4372(3) 0.7523(2) 0.39923(18) 0.0264(6) Uani 1 1 d . . . . .
C73 C 0.5948(3) 0.7461(2) 0.36123(19) 0.0281(6) Uani 1 1 d . . . . .
O74 O 0.3499(3) 0.79064(18) 0.18718(14) 0.0364(5) Uani 1 1 d . . . . .
O75 O 0.7226(3) 0.7299(2) 0.39304(14) 0.0427(6) Uani 1 1 d . . . . .
C101 C 0.6792(9) 0.5369(6) 0.6029(5) 0.0628(16) Uani 0.609(6) 1 d . . P A 1
H10A H 0.711278 0.494268 0.646452 0.075 Uiso 0.609(6) 1 calc R U P A 1
H10B H 0.562596 0.510029 0.582952 0.075 Uiso 0.609(6) 1 calc R U P A 1
Cl1A Cl 0.7879(4) 0.52234(18) 0.52485(12) 0.1545(10) Uani 0.609(6) 1 d . . P A
1
Cl2A Cl 0.69158(17) 0.66153(9) 0.65226(7) 0.0720(4) Uani 0.609(6) 1 d . . P A 1
C111 C 0.8156(14) 0.6251(9) 0.5821(7) 0.0628(16) Uani 0.391(6) 1 d . . P A 2
H11A H 0.829416 0.678505 0.543023 0.075 Uiso 0.391(6) 1 calc R U P A 2
H11B H 0.924130 0.630301 0.614084 0.075 Uiso 0.391(6) 1 calc R U P A 2
Cl1B Cl 0.7879(4) 0.52234(18) 0.52485(12) 0.1545(10) Uani 0.391(6) 1 d . . P A
2
Cl2B Cl 0.69158(17) 0.66153(9) 0.65226(7) 0.0720(4) Uani 0.391(6) 1 d . . P A 2



#------------------------------------------------------------------------------#
#                              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
S1 C14 1.740(3) . ?
S1 C1 1.741(3) . ?
C1 C6 1.396(4) . ?
C1 C2 1.396(4) . ?
C2 C3 1.369(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.403(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.403(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.480(4) . ?
C7 O8 1.226(3) . ?
C7 C9 1.490(4) . ?
C9 C14 1.407(3) . ?
C9 C10 1.420(4) . ?
C10 C11 1.375(4) . ?
C10 N25 1.428(3) . ?
C11 C12 1.395(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.367(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.405(4) . ?
C13 H13 0.9500 . ?
N25 C26 1.397(3) . ?
N25 C33 1.413(3) . ?
C26 O34 1.207(3) . ?
C26 C27 1.488(4) . ?
C27 C32 1.383(4) . ?
C27 C28 1.385(4) . ?
C28 C29 1.392(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.390(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.388(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.384(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.486(3) . ?
C33 O35 1.203(3) . ?
S2 C64 1.741(3) . ?
S2 C51 1.742(3) . ?
C51 C52 1.395(4) . ?
C51 C56 1.402(4) . ?
C52 C53 1.378(4) . ?
C52 H52 0.9500 . ?
C53 C54 1.397(4) . ?
C53 H53 0.9500 . ?
C54 C55 1.375(4) . ?
C54 H54 0.9500 . ?
C55 C56 1.401(4) . ?
C55 H55 0.9500 . ?
C56 C57 1.483(4) . ?
C57 O58 1.224(3) . ?
C57 C59 1.491(4) . ?
C59 C64 1.403(4) . ?
C59 C60 1.416(4) . ?
C60 C61 1.377(4) . ?
C60 N65 1.431(3) . ?
C61 C62 1.394(4) . ?
C61 H61 0.9500 . ?
C62 C63 1.367(4) . ?
C62 H62 0.9500 . ?
C63 C64 1.408(4) . ?
C63 H63 0.9500 . ?
N65 C66 1.397(3) . ?
N65 C73 1.402(4) . ?
C66 O74 1.211(4) . ?
C66 C67 1.488(4) . ?
C67 C68 1.380(4) . ?
C67 C72 1.387(4) . ?
C68 C69 1.390(4) . ?
C68 H68 0.9500 . ?
C69 C70 1.389(4) . ?
C69 H69 0.9500 . ?
C70 C71 1.389(4) . ?
C70 H70 0.9500 . ?
C71 C72 1.380(4) . ?
C71 H71 0.9500 . ?
C72 C73 1.488(4) . ?
C73 O75 1.204(3) . ?
C101 Cl1A 1.602(8) . ?
C101 Cl2A 1.766(8) . ?
C101 H10A 0.9900 . ?
C101 H10B 0.9900 . ?
C111 Cl1B 1.555(12) . ?
C111 Cl2B 1.665(12) . ?
C111 H11A 0.9900 . ?
C111 H11B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 S1 C1 103.55(13) . . ?
C6 C1 C2 120.4(3) . . ?
C6 C1 S1 123.5(2) . . ?
C2 C1 S1 116.2(2) . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 118.4(3) . . ?
C1 C6 C7 124.4(2) . . ?
C5 C6 C7 117.2(2) . . ?
O8 C7 C6 119.0(2) . . ?
O8 C7 C9 121.3(3) . . ?
C6 C7 C9 119.6(2) . . ?
C14 C9 C10 116.5(2) . . ?
C14 C9 C7 122.0(2) . . ?
C10 C9 C7 121.4(2) . . ?
C11 C10 C9 122.1(2) . . ?
C11 C10 N25 117.0(2) . . ?
C9 C10 N25 120.9(2) . . ?
C10 C11 C12 119.9(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.7(2) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C9 120.8(2) . . ?
C13 C14 S1 114.21(19) . . ?
C9 C14 S1 125.0(2) . . ?
C26 N25 C33 112.1(2) . . ?
C26 N25 C10 123.4(2) . . ?
C33 N25 C10 123.8(2) . . ?
O34 C26 N25 125.8(2) . . ?
O34 C26 C27 128.9(2) . . ?
N25 C26 C27 105.4(2) . . ?
C32 C27 C28 121.7(2) . . ?
C32 C27 C26 108.9(2) . . ?
C28 C27 C26 129.3(3) . . ?
C27 C28 C29 117.1(3) . . ?
C27 C28 H28 121.5 . . ?
C29 C28 H28 121.5 . . ?
C30 C29 C28 121.0(3) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C31 C30 C29 121.6(3) . . ?
C31 C30 H30 119.2 . . ?
C29 C30 H30 119.2 . . ?
C32 C31 C30 117.0(3) . . ?
C32 C31 H31 121.5 . . ?
C30 C31 H31 121.5 . . ?
C27 C32 C31 121.5(2) . . ?
C27 C32 C33 108.3(2) . . ?
C31 C32 C33 130.2(3) . . ?
O35 C33 N25 124.7(2) . . ?
O35 C33 C32 129.9(2) . . ?
N25 C33 C32 105.3(2) . . ?
C64 S2 C51 104.04(13) . . ?
C52 C51 C56 120.9(3) . . ?
C52 C51 S2 115.8(2) . . ?
C56 C51 S2 123.4(2) . . ?
C53 C52 C51 119.8(3) . . ?
C53 C52 H52 120.1 . . ?
C51 C52 H52 120.1 . . ?
C52 C53 C54 120.3(3) . . ?
C52 C53 H53 119.8 . . ?
C54 C53 H53 119.8 . . ?
C55 C54 C53 119.6(3) . . ?
C55 C54 H54 120.2 . . ?
C53 C54 H54 120.2 . . ?
C54 C55 C56 121.6(3) . . ?
C54 C55 H55 119.2 . . ?
C56 C55 H55 119.2 . . ?
C55 C56 C51 117.8(3) . . ?
C55 C56 C57 117.6(2) . . ?
C51 C56 C57 124.6(3) . . ?
O58 C57 C56 118.9(3) . . ?
O58 C57 C59 121.3(3) . . ?
C56 C57 C59 119.8(2) . . ?
C64 C59 C60 116.3(2) . . ?
C64 C59 C57 122.4(3) . . ?
C60 C59 C57 121.3(2) . . ?
C61 C60 C59 122.2(2) . . ?
C61 C60 N65 116.1(2) . . ?
C59 C60 N65 121.7(2) . . ?
C60 C61 C62 119.8(3) . . ?
C60 C61 H61 120.1 . . ?
C62 C61 H61 120.1 . . ?
C63 C62 C61 120.2(3) . . ?
C63 C62 H62 119.9 . . ?
C61 C62 H62 119.9 . . ?
C62 C63 C64 120.0(2) . . ?
C62 C63 H63 120.0 . . ?
C64 C63 H63 120.0 . . ?
C59 C64 C63 121.5(3) . . ?
C59 C64 S2 125.3(2) . . ?
C63 C64 S2 113.1(2) . . ?
C66 N65 C73 112.0(2) . . ?
C66 N65 C60 125.1(2) . . ?
C73 N65 C60 122.6(2) . . ?
O74 C66 N65 125.2(3) . . ?
O74 C66 C67 129.1(2) . . ?
N65 C66 C67 105.7(2) . . ?
C68 C67 C72 121.2(3) . . ?
C68 C67 C66 130.4(3) . . ?
C72 C67 C66 108.4(2) . . ?
C67 C68 C69 117.7(3) . . ?
C67 C68 H68 121.2 . . ?
C69 C68 H68 121.2 . . ?
C70 C69 C68 120.8(3) . . ?
C70 C69 H69 119.6 . . ?
C68 C69 H69 119.6 . . ?
C69 C70 C71 121.5(3) . . ?
C69 C70 H70 119.2 . . ?
C71 C70 H70 119.2 . . ?
C72 C71 C70 117.1(3) . . ?
C72 C71 H71 121.5 . . ?
C70 C71 H71 121.5 . . ?
C71 C72 C67 121.7(3) . . ?
C71 C72 C73 130.1(3) . . ?
C67 C72 C73 108.2(2) . . ?
O75 C73 N65 124.5(3) . . ?
O75 C73 C72 129.8(3) . . ?
N65 C73 C72 105.7(2) . . ?
Cl1A C101 Cl2A 117.4(4) . . ?
Cl1A C101 H10A 108.0 . . ?
Cl2A C101 H10A 108.0 . . ?
Cl1A C101 H10B 108.0 . . ?
Cl2A C101 H10B 108.0 . . ?
H10A C101 H10B 107.2 . . ?
Cl1B C111 Cl2B 126.6(7) . . ?
Cl1B C111 H11A 105.7 . . ?
Cl2B C111 H11A 105.7 . . ?
Cl1B C111 H11B 105.7 . . ?
Cl2B C111 H11B 105.6 . . ?
H11A C111 H11B 106.1 . . ?

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
C14 S1 C1 C6 -10.3(3) . . . . ?
C14 S1 C1 C2 170.9(2) . . . . ?
C6 C1 C2 C3 1.3(5) . . . . ?
S1 C1 C2 C3 -179.9(2) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C3 C4 C5 C6 1.3(5) . . . . ?
C2 C1 C6 C5 -0.9(4) . . . . ?
S1 C1 C6 C5 -179.6(2) . . . . ?
C2 C1 C6 C7 178.6(3) . . . . ?
S1 C1 C6 C7 0.0(4) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C4 C5 C6 C7 -180.0(3) . . . . ?
C1 C6 C7 O8 -170.2(3) . . . . ?
C5 C6 C7 O8 9.4(4) . . . . ?
C1 C6 C7 C9 11.3(4) . . . . ?
C5 C6 C7 C9 -169.1(2) . . . . ?
O8 C7 C9 C14 172.2(3) . . . . ?
C6 C7 C9 C14 -9.3(4) . . . . ?
O8 C7 C9 C10 -9.8(4) . . . . ?
C6 C7 C9 C10 168.7(2) . . . . ?
C14 C9 C10 C11 3.4(4) . . . . ?
C7 C9 C10 C11 -174.8(2) . . . . ?
C14 C9 C10 N25 -177.7(2) . . . . ?
C7 C9 C10 N25 4.1(4) . . . . ?
C9 C10 C11 C12 -1.9(4) . . . . ?
N25 C10 C11 C12 179.2(2) . . . . ?
C10 C11 C12 C13 -1.1(4) . . . . ?
C11 C12 C13 C14 2.4(4) . . . . ?
C12 C13 C14 C9 -0.8(4) . . . . ?
C12 C13 C14 S1 179.0(2) . . . . ?
C10 C9 C14 C13 -2.0(4) . . . . ?
C7 C9 C14 C13 176.1(2) . . . . ?
C10 C9 C14 S1 178.3(2) . . . . ?
C7 C9 C14 S1 -3.6(4) . . . . ?
C1 S1 C14 C13 -167.5(2) . . . . ?
C1 S1 C14 C9 12.2(3) . . . . ?
C11 C10 N25 C26 77.3(3) . . . . ?
C9 C10 N25 C26 -101.7(3) . . . . ?
C11 C10 N25 C33 -113.8(3) . . . . ?
C9 C10 N25 C33 67.3(4) . . . . ?
C33 N25 C26 O34 179.3(3) . . . . ?
C10 N25 C26 O34 -10.6(4) . . . . ?
C33 N25 C26 C27 -1.1(3) . . . . ?
C10 N25 C26 C27 169.0(2) . . . . ?
O34 C26 C27 C32 179.2(3) . . . . ?
N25 C26 C27 C32 -0.3(3) . . . . ?
O34 C26 C27 C28 2.1(5) . . . . ?
N25 C26 C27 C28 -177.4(3) . . . . ?
C32 C27 C28 C29 -1.3(4) . . . . ?
C26 C27 C28 C29 175.4(3) . . . . ?
C27 C28 C29 C30 0.3(4) . . . . ?
C28 C29 C30 C31 1.2(5) . . . . ?
C29 C30 C31 C32 -1.6(4) . . . . ?
C28 C27 C32 C31 0.9(4) . . . . ?
C26 C27 C32 C31 -176.4(3) . . . . ?
C28 C27 C32 C33 178.8(3) . . . . ?
C26 C27 C32 C33 1.5(3) . . . . ?
C30 C31 C32 C27 0.5(4) . . . . ?
C30 C31 C32 C33 -176.9(3) . . . . ?
C26 N25 C33 O35 -175.4(3) . . . . ?
C10 N25 C33 O35 14.5(4) . . . . ?
C26 N25 C33 C32 2.0(3) . . . . ?
C10 N25 C33 C32 -168.1(2) . . . . ?
C27 C32 C33 O35 175.1(3) . . . . ?
C31 C32 C33 O35 -7.2(5) . . . . ?
C27 C32 C33 N25 -2.1(3) . . . . ?
C31 C32 C33 N25 175.6(3) . . . . ?
C64 S2 C51 C52 -179.2(2) . . . . ?
C64 S2 C51 C56 0.7(3) . . . . ?
C56 C51 C52 C53 -1.9(4) . . . . ?
S2 C51 C52 C53 178.0(2) . . . . ?
C51 C52 C53 C54 -0.5(5) . . . . ?
C52 C53 C54 C55 1.7(5) . . . . ?
C53 C54 C55 C56 -0.6(4) . . . . ?
C54 C55 C56 C51 -1.7(4) . . . . ?
C54 C55 C56 C57 176.3(3) . . . . ?
C52 C51 C56 C55 2.9(4) . . . . ?
S2 C51 C56 C55 -177.0(2) . . . . ?
C52 C51 C56 C57 -174.9(3) . . . . ?
S2 C51 C56 C57 5.2(4) . . . . ?
C55 C56 C57 O58 -5.4(4) . . . . ?
C51 C56 C57 O58 172.4(3) . . . . ?
C55 C56 C57 C59 174.7(3) . . . . ?
C51 C56 C57 C59 -7.5(4) . . . . ?
O58 C57 C59 C64 -176.9(3) . . . . ?
C56 C57 C59 C64 2.9(4) . . . . ?
O58 C57 C59 C60 5.0(5) . . . . ?
C56 C57 C59 C60 -175.2(3) . . . . ?
C64 C59 C60 C61 -1.2(4) . . . . ?
C57 C59 C60 C61 177.0(3) . . . . ?
C64 C59 C60 N65 -179.5(2) . . . . ?
C57 C59 C60 N65 -1.3(4) . . . . ?
C59 C60 C61 C62 0.0(4) . . . . ?
N65 C60 C61 C62 178.5(3) . . . . ?
C60 C61 C62 C63 0.6(4) . . . . ?
C61 C62 C63 C64 0.0(4) . . . . ?
C60 C59 C64 C63 1.8(4) . . . . ?
C57 C59 C64 C63 -176.4(3) . . . . ?
C60 C59 C64 S2 -178.4(2) . . . . ?
C57 C59 C64 S2 3.4(4) . . . . ?
C62 C63 C64 C59 -1.3(4) . . . . ?
C62 C63 C64 S2 178.9(2) . . . . ?
C51 S2 C64 C59 -4.9(3) . . . . ?
C51 S2 C64 C63 174.9(2) . . . . ?
C61 C60 N65 C66 102.8(3) . . . . ?
C59 C60 N65 C66 -78.7(4) . . . . ?
C61 C60 N65 C73 -84.5(3) . . . . ?
C59 C60 N65 C73 94.0(3) . . . . ?
C73 N65 C66 O74 -178.1(3) . . . . ?
C60 N65 C66 O74 -4.7(5) . . . . ?
C73 N65 C66 C67 2.7(3) . . . . ?
C60 N65 C66 C67 176.1(2) . . . . ?
O74 C66 C67 C68 0.9(5) . . . . ?
N65 C66 C67 C68 -180.0(3) . . . . ?
O74 C66 C67 C72 179.3(3) . . . . ?
N65 C66 C67 C72 -1.5(3) . . . . ?
C72 C67 C68 C69 0.1(4) . . . . ?
C66 C67 C68 C69 178.3(3) . . . . ?
C67 C68 C69 C70 0.3(5) . . . . ?
C68 C69 C70 C71 -0.3(5) . . . . ?
C69 C70 C71 C72 -0.2(5) . . . . ?
C70 C71 C72 C67 0.6(5) . . . . ?
C70 C71 C72 C73 -178.2(3) . . . . ?
C68 C67 C72 C71 -0.6(5) . . . . ?
C66 C67 C72 C71 -179.2(3) . . . . ?
C68 C67 C72 C73 178.5(3) . . . . ?
C66 C67 C72 C73 -0.1(3) . . . . ?
C66 N65 C73 O75 177.6(3) . . . . ?
C60 N65 C73 O75 4.1(5) . . . . ?
C66 N65 C73 C72 -2.8(3) . . . . ?
C60 N65 C73 C72 -176.3(2) . . . . ?
C71 C72 C73 O75 0.2(6) . . . . ?
C67 C72 C73 O75 -178.7(3) . . . . ?
C71 C72 C73 N65 -179.3(3) . . . . ?
C67 C72 C73 N65 1.7(3) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_NM253
_database_code_depnum_ccdc_archive 'CCDC 2204835'
loop_
_audit_author_name
_audit_author_address
'Thierry ROISNEL'
;Institut des Sciences Chimiques de Rennes
France
;
_audit_update_record             
;
2022-09-01 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 20 avril 2022                                            #
#------------------------------------------------------------------------------#


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H8 Cl F2 N O'
_chemical_formula_sum            'C12 H8 Cl F2 N O'
_chemical_formula_weight         255.64
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
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                   13.651(2)
_cell_length_b                   5.9725(11)
_cell_length_c                   13.013(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.997(6)
_cell_angle_gamma                90
_cell_volume                     1060.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9851
_cell_measurement_theta_min      3.4111
_cell_measurement_theta_max      27.5064
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.0238054
_diffrn_orient_matrix_UB_21      0.0579114
_diffrn_orient_matrix_UB_31      0.0445719
_diffrn_orient_matrix_UB_12      -0.1583053
_diffrn_orient_matrix_UB_22      -0.0300527
_diffrn_orient_matrix_UB_32      -0.0455025
_diffrn_orient_matrix_UB_13      -0.0077702
_diffrn_orient_matrix_UB_23      -0.0453721
_diffrn_orient_matrix_UB_33      0.0569996


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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             520
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_T_max  0.902

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

# Software                   : BIS V6.2.15/2021-03-15 && APEX4 2021.10-0       #
# Number of scans            :        4                                        #
# Total number of frames [*] :      474                                        #
# Total length of scans  [*] :   474.00 (deg.)                                 #
# Rotation speed         [*] :     8.00 sec./deg.                              #
# Total exposition time  [*] :      1 h   3.2 min.                             #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Fast     1.0  1.00    34.0   180  180.0    0.0    0.0    0.0   54.7 150.0 #
#  2 Phi      8.0  1.00    34.0   192  192.0    0.1  270.3  188.0   24.0 150.0 #
#  3 Omega    8.0  1.00    34.0    97   97.0    0.1    2.7    0.0  -44.5 150.0 #
#  4 Phi      8.0  1.00    34.0   185  185.0    0.1    1.9  284.0  -24.0 150.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0213
_diffrn_reflns_av_r_equivalents  0.0298
_diffrn_reflns_number            17873
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.493
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.977
_reflns_number_total             2387
_reflns_number_gt                2290
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

#------------------------------------------------------------------------------#
#                            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     
'w=1/[σ²(Fo²)+(0.0374P)²+0.4689P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2387
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0757
_refine_ls_wR_factor_gt          0.0746
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.046

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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 0.60972(5) 0.48210(13) 0.48647(6) 0.02878(19) Uani 1 1 d . . . . .
C2 C 0.61580(8) 0.33422(19) 0.40775(8) 0.0193(2) Uani 1 1 d . . . . .
C3 C 0.54334(8) 0.1757(2) 0.39720(9) 0.0225(2) Uani 1 1 d . . . . .
H3 H 0.490273 0.171072 0.443418 0.027 Uiso 1 1 calc R U . . .
C4 C 0.54962(9) 0.0225(2) 0.31723(10) 0.0258(3) Uani 1 1 d . . . . .
H4 H 0.501084 -0.090267 0.308683 0.031 Uiso 1 1 calc R U . . .
C5 C 0.62715(9) 0.0351(2) 0.24995(10) 0.0273(3) Uani 1 1 d . . . . .
H5 H 0.631423 -0.068978 0.194991 0.033 Uiso 1 1 calc R U . . .
C6 C 0.69858(8) 0.1990(2) 0.26252(9) 0.0233(2) Uani 1 1 d . . . . .
H6 H 0.750789 0.206640 0.215328 0.028 Uiso 1 1 calc R U . . .
C7 C 0.69505(8) 0.35189(19) 0.34289(8) 0.0179(2) Uani 1 1 d . . . . .
C8 C 0.77290(8) 0.53182(19) 0.35956(8) 0.0184(2) Uani 1 1 d . . . . .
H8 H 0.741126 0.682465 0.355192 0.022 Uiso 1 1 calc R U . . .
O9 O 0.84666(6) 0.51817(16) 0.28466(7) 0.0246(2) Uani 1 1 d . . . . .
H9 H 0.8407(12) 0.623(3) 0.2442(13) 0.030 Uiso 1 1 d . U . . .
C10 C 0.82285(8) 0.50710(18) 0.46427(8) 0.0173(2) Uani 1 1 d . . . . .
C11 C 0.88547(8) 0.32917(19) 0.48601(8) 0.0189(2) Uani 1 1 d . . . . .
F12 F 0.89894(5) 0.17277(12) 0.41348(5) 0.02480(17) Uani 1 1 d . . . . .
C13 C 0.93517(8) 0.3057(2) 0.57830(9) 0.0229(2) Uani 1 1 d . . . . .
H13 H 0.977399 0.182155 0.591455 0.027 Uiso 1 1 calc R U . . .
C14 C 0.92058(8) 0.4708(2) 0.65096(9) 0.0244(3) Uani 1 1 d . . . . .
H14 H 0.954619 0.459683 0.715054 0.029 Uiso 1 1 calc R U . . .
N15 N 0.86087(7) 0.64525(18) 0.63529(8) 0.0229(2) Uani 1 1 d . . . . .
C16 C 0.81456(8) 0.65900(19) 0.54505(9) 0.0190(2) Uani 1 1 d . . . . .
Cl1 Cl 0.73756(2) 0.88944(5) 0.53237(2) 0.02552(10) 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
F1 C2 1.3562(13) . ?
C2 C3 1.3741(16) . ?
C2 C7 1.3878(15) . ?
C3 C4 1.3896(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3872(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3893(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.3900(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.5242(15) . ?
C8 O9 1.4158(13) . ?
C8 C10 1.5202(15) . ?
C8 H8 1.0000 . ?
O9 H9 0.822(18) . ?
C10 C11 1.3899(16) . ?
C10 C16 1.3946(16) . ?
C11 F12 1.3428(13) . ?
C11 C13 1.3762(16) . ?
C13 C14 1.3830(18) . ?
C13 H13 0.9500 . ?
C14 N15 1.3363(17) . ?
C14 H14 0.9500 . ?
N15 C16 1.3264(16) . ?
C16 Cl1 1.7379(12) . ?

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
F1 C2 C3 118.08(10) . . ?
F1 C2 C7 117.93(10) . . ?
C3 C2 C7 123.99(11) . . ?
C2 C3 C4 118.35(11) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 119.65(11) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.36(11) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 121.21(11) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C2 C7 C6 116.44(10) . . ?
C2 C7 C8 121.07(10) . . ?
C6 C7 C8 122.49(10) . . ?
O9 C8 C10 107.35(9) . . ?
O9 C8 C7 111.34(9) . . ?
C10 C8 C7 111.09(9) . . ?
O9 C8 H8 109.0 . . ?
C10 C8 H8 109.0 . . ?
C7 C8 H8 109.0 . . ?
C8 O9 H9 109.5(11) . . ?
C11 C10 C16 113.68(10) . . ?
C11 C10 C8 121.42(10) . . ?
C16 C10 C8 124.85(10) . . ?
F12 C11 C13 118.10(10) . . ?
F12 C11 C10 118.69(10) . . ?
C13 C11 C10 123.21(11) . . ?
C11 C13 C14 116.70(11) . . ?
C11 C13 H13 121.7 . . ?
C14 C13 H13 121.7 . . ?
N15 C14 C13 123.11(11) . . ?
N15 C14 H14 118.4 . . ?
C13 C14 H14 118.4 . . ?
C16 N15 C14 117.61(10) . . ?
N15 C16 C10 125.69(11) . . ?
N15 C16 Cl1 114.28(9) . . ?
C10 C16 Cl1 120.03(9) . . ?

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
F1 C2 C3 C4 -179.44(10) . . . . ?
C7 C2 C3 C4 0.39(18) . . . . ?
C2 C3 C4 C5 -0.92(17) . . . . ?
C3 C4 C5 C6 0.35(19) . . . . ?
C4 C5 C6 C7 0.79(19) . . . . ?
F1 C2 C7 C6 -179.48(10) . . . . ?
C3 C2 C7 C6 0.70(17) . . . . ?
F1 C2 C7 C8 0.02(15) . . . . ?
C3 C2 C7 C8 -179.81(10) . . . . ?
C5 C6 C7 C2 -1.28(17) . . . . ?
C5 C6 C7 C8 179.24(11) . . . . ?
C2 C7 C8 O9 179.89(10) . . . . ?
C6 C7 C8 O9 -0.66(15) . . . . ?
C2 C7 C8 C10 60.30(13) . . . . ?
C6 C7 C8 C10 -120.24(11) . . . . ?
O9 C8 C10 C11 -51.99(13) . . . . ?
C7 C8 C10 C11 69.96(13) . . . . ?
O9 C8 C10 C16 125.41(11) . . . . ?
C7 C8 C10 C16 -112.65(12) . . . . ?
C16 C10 C11 F12 -179.95(9) . . . . ?
C8 C10 C11 F12 -2.28(15) . . . . ?
C16 C10 C11 C13 -0.40(15) . . . . ?
C8 C10 C11 C13 177.27(10) . . . . ?
F12 C11 C13 C14 179.30(10) . . . . ?
C10 C11 C13 C14 -0.25(17) . . . . ?
C11 C13 C14 N15 0.76(17) . . . . ?
C13 C14 N15 C16 -0.54(17) . . . . ?
C14 N15 C16 C10 -0.23(16) . . . . ?
C14 N15 C16 Cl1 179.28(8) . . . . ?
C11 C10 C16 N15 0.67(16) . . . . ?
C8 C10 C16 N15 -176.91(10) . . . . ?
C11 C10 C16 Cl1 -178.82(8) . . . . ?
C8 C10 C16 Cl1 3.61(15) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_NM082
_database_code_depnum_ccdc_archive 'CCDC 2204836'
loop_
_audit_author_name
_audit_author_address
'Thierry ROISNEL'
;Institut des Sciences Chimiques de Rennes
France
;
_audit_update_record             
;
2022-09-01 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 06 avril 2021                                            #
#------------------------------------------------------------------------------#


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H19 F2 N O3'
_chemical_formula_sum            'C18 H19 F2 N O3'
_chemical_formula_weight         335.34
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
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                   11.5846(9)
_cell_length_b                   7.0406(5)
_cell_length_c                   21.0857(13)
_cell_angle_alpha                90
_cell_angle_beta                 101.424(2)
_cell_angle_gamma                90
_cell_volume                     1685.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3304
_cell_measurement_theta_min      2.8940
_cell_measurement_theta_max      26.5231
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0294361
_diffrn_orient_matrix_UB_21      0.0813418
_diffrn_orient_matrix_UB_31      0.0165963
_diffrn_orient_matrix_UB_12      -0.0478161
_diffrn_orient_matrix_UB_22      0.0431419
_diffrn_orient_matrix_UB_32      -0.1266382
_diffrn_orient_matrix_UB_13      -0.0385643
_diffrn_orient_matrix_UB_23      0.0199619
_diffrn_orient_matrix_UB_33      0.0213616


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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             704
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_T_max  0.975

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

# Software                   : BIS 2014.5.0.0/23-May-2014 && APEX2_2014.11-0   #
# Number of scans            :        3                                        #
# Total number of frames     :      283                                        #
# Total length of scans      :   283.00 (deg.)                                 #
# Rotation speed             :    20.00 sec./deg.                              #
# Total exposition time      :      1 h  34.3 min.                             #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range  Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Omega   20.0  1.00    35.0    93   93.0  344.0  341.7   84.8  335.2 150.0 #
#  2 Omega   20.0  1.00    35.0    97   97.0  344.0  249.8  227.4   32.6 150.0 #
#  3 Omega   20.0  1.00    35.0    93   93.0  344.0  341.3  357.4  336.0 150.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.33
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_uneti/neti     0.0362
_diffrn_reflns_av_r_equivalents  0.0276
_diffrn_reflns_number            10790
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.057
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_reflns_number_total             3823
_reflns_number_gt                2812
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

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

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'

#------------------------------------------------------------------------------#
#                            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     
'w=1/[σ²(Fo²)+(0.1039P)²+0.4376P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3823
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1431
_refine_ls_wR_factor_gt          0.1244
_refine_ls_goodness_of_fit_ref   0.840
_refine_ls_restrained_S_all      0.840
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.041

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 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'

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 0.30513(11) 0.25330(16) 0.68002(5) 0.0458(3) Uani 1 1 d . . . . .
C2 C 0.25618(15) 0.4074(3) 0.64568(8) 0.0307(4) Uani 1 1 d . . . . .
C3 C 0.24506(16) 0.5705(3) 0.67972(8) 0.0366(4) Uani 1 1 d . . . . .
H3 H 0.273034 0.576350 0.725181 0.044 Uiso 1 1 calc R U . . .
C4 C 0.19205(16) 0.7256(3) 0.64592(8) 0.0334(4) Uani 1 1 d . . . . .
H4 H 0.184177 0.840394 0.668341 0.040 Uiso 1 1 calc R U . . .
C5 C 0.15015(14) 0.7161(2) 0.57975(8) 0.0265(4) Uani 1 1 d . . . . .
H5 H 0.111208 0.822147 0.557175 0.032 Uiso 1 1 calc R U . . .
C6 C 0.16554(12) 0.5501(2) 0.54663(7) 0.0206(3) Uani 1 1 d . . . . .
C7 C 0.22007(13) 0.3900(2) 0.57929(7) 0.0230(3) Uani 1 1 d . . . . .
C8 C 0.23976(14) 0.2079(2) 0.54436(8) 0.0258(4) Uani 1 1 d . . . . .
H8 H 0.265209 0.106355 0.577329 0.031 Uiso 1 1 calc R U . . .
O9 O 0.12851(10) 0.15474(16) 0.50553(6) 0.0284(3) Uani 1 1 d . . . . .
H9 H 0.1395(17) 0.043(3) 0.4885(9) 0.034 Uiso 1 1 d . U . . .
C10 C 0.33487(14) 0.2317(2) 0.50421(8) 0.0254(4) Uani 1 1 d . . . . .
C11 C 0.31106(16) 0.2437(2) 0.43734(9) 0.0320(4) Uani 1 1 d . . . . .
H11 H 0.231780 0.238652 0.414421 0.038 Uiso 1 1 calc R U . . .
C12 C 0.40187(19) 0.2630(3) 0.40318(10) 0.0420(5) Uani 1 1 d . . . . .
H12 H 0.383890 0.272919 0.357346 0.050 Uiso 1 1 calc R U . . .
C13 C 0.51780(18) 0.2677(3) 0.43556(11) 0.0425(5) Uani 1 1 d . . . . .
H13 H 0.579338 0.279832 0.411996 0.051 Uiso 1 1 calc R U . . .
C14 C 0.54402(17) 0.2550(3) 0.50187(11) 0.0412(5) Uani 1 1 d . . . . .
H14 H 0.623421 0.257496 0.524681 0.049 Uiso 1 1 calc R U . . .
C15 C 0.45253(16) 0.2384(2) 0.53464(9) 0.0314(4) Uani 1 1 d . . . . .
F16 F 0.47800(10) 0.22646(17) 0.60004(6) 0.0474(3) Uani 1 1 d . . . . .
N17 N 0.12211(11) 0.53227(19) 0.47949(6) 0.0211(3) Uani 1 1 d . . . . .
H17 H 0.1047(15) 0.421(3) 0.4673(8) 0.025 Uiso 1 1 d . U . . .
C18 C 0.12596(13) 0.6659(2) 0.43403(7) 0.0215(3) Uani 1 1 d . . . . .
O19 O 0.16188(11) 0.82750(15) 0.44393(5) 0.0292(3) Uani 1 1 d . . . . .
O20 O 0.08543(10) 0.59004(17) 0.37552(5) 0.0294(3) Uani 1 1 d . . . . .
C21 C 0.08988(18) 0.6970(3) 0.31574(8) 0.0436(5) Uani 1 1 d . . . . .
C22 C 0.0379(2) 0.5536(4) 0.26407(9) 0.0705(9) Uani 1 1 d . . . . .
H22A H 0.084833 0.436788 0.270131 0.106 Uiso 1 1 calc R U . . .
H22B H 0.038729 0.606593 0.221192 0.106 Uiso 1 1 calc R U . . .
H22C H -0.043369 0.524818 0.267577 0.106 Uiso 1 1 calc R U . . .
C23 C 0.21723(19) 0.7410(4) 0.31310(10) 0.0547(6) Uani 1 1 d . . . . .
H23A H 0.248177 0.835600 0.346204 0.082 Uiso 1 1 calc R U . . .
H23B H 0.221453 0.791143 0.270270 0.082 Uiso 1 1 calc R U . . .
H23C H 0.264200 0.624535 0.321133 0.082 Uiso 1 1 calc R U . . .
C24 C 0.0140(2) 0.8735(4) 0.31268(12) 0.0678(8) Uani 1 1 d . . . . .
H24A H -0.064045 0.838597 0.320241 0.102 Uiso 1 1 calc R U . . .
H24B H 0.005989 0.932224 0.269891 0.102 Uiso 1 1 calc R U . . .
H24C H 0.051015 0.963793 0.345934 0.102 Uiso 1 1 calc R U . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.364(2) . ?
C2 C3 1.374(3) . ?
C2 C7 1.385(2) . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.404(2) . ?
C6 N17 1.4111(19) . ?
C7 C8 1.519(2) . ?
C8 O9 1.433(2) . ?
C8 C10 1.526(2) . ?
C8 H8 1.0000 . ?
O9 H9 0.88(2) . ?
C10 C11 1.385(2) . ?
C10 C15 1.388(2) . ?
C11 C12 1.394(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.374(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 F16 1.354(2) . ?
N17 C18 1.350(2) . ?
N17 H17 0.83(2) . ?
C18 O19 1.2153(19) . ?
C18 O20 1.3411(18) . ?
O20 C21 1.478(2) . ?
C21 C24 1.516(4) . ?
C21 C22 1.520(3) . ?
C21 C23 1.519(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C2 C3 117.36(14) . . ?
F1 C2 C7 118.51(15) . . ?
C3 C2 C7 124.13(16) . . ?
C2 C3 C4 118.02(15) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C3 C4 C5 120.91(16) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 119.47(15) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C7 121.21(14) . . ?
C5 C6 N17 121.54(14) . . ?
C7 C6 N17 117.19(13) . . ?
C2 C7 C6 116.20(14) . . ?
C2 C7 C8 121.36(14) . . ?
C6 C7 C8 122.43(13) . . ?
O9 C8 C7 107.05(13) . . ?
O9 C8 C10 112.23(13) . . ?
C7 C8 C10 111.76(12) . . ?
O9 C8 H8 108.6 . . ?
C7 C8 H8 108.6 . . ?
C10 C8 H8 108.6 . . ?
C8 O9 H9 106.2(13) . . ?
C11 C10 C15 116.62(16) . . ?
C11 C10 C8 123.48(15) . . ?
C15 C10 C8 119.89(15) . . ?
C10 C11 C12 120.90(18) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 120.42(19) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 119.92(18) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 118.58(18) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
F16 C15 C14 118.75(17) . . ?
F16 C15 C10 117.69(16) . . ?
C14 C15 C10 123.56(18) . . ?
C18 N17 C6 126.50(13) . . ?
C18 N17 H17 118.2(12) . . ?
C6 N17 H17 114.2(12) . . ?
O19 C18 O20 125.20(14) . . ?
O19 C18 N17 126.07(14) . . ?
O20 C18 N17 108.72(13) . . ?
C18 O20 C21 121.11(14) . . ?
O20 C21 C24 109.65(16) . . ?
O20 C21 C22 101.35(16) . . ?
C24 C21 C22 111.7(2) . . ?
O20 C21 C23 109.46(15) . . ?
C24 C21 C23 113.0(2) . . ?
C22 C21 C23 111.03(19) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C2 C3 C4 -177.83(15) . . . . ?
C7 C2 C3 C4 1.6(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 -2.3(2) . . . . ?
C4 C5 C6 C7 1.7(2) . . . . ?
C4 C5 C6 N17 178.58(14) . . . . ?
F1 C2 C7 C6 177.26(14) . . . . ?
C3 C2 C7 C6 -2.2(2) . . . . ?
F1 C2 C7 C8 -3.2(2) . . . . ?
C3 C2 C7 C8 177.37(15) . . . . ?
C5 C6 C7 C2 0.5(2) . . . . ?
N17 C6 C7 C2 -176.55(13) . . . . ?
C5 C6 C7 C8 -179.07(14) . . . . ?
N17 C6 C7 C8 3.9(2) . . . . ?
C2 C7 C8 O9 128.26(15) . . . . ?
C6 C7 C8 O9 -52.24(18) . . . . ?
C2 C7 C8 C10 -108.49(17) . . . . ?
C6 C7 C8 C10 71.02(19) . . . . ?
O9 C8 C10 C11 13.8(2) . . . . ?
C7 C8 C10 C11 -106.44(17) . . . . ?
O9 C8 C10 C15 -164.82(13) . . . . ?
C7 C8 C10 C15 74.91(18) . . . . ?
C15 C10 C11 C12 -0.5(2) . . . . ?
C8 C10 C11 C12 -179.18(16) . . . . ?
C10 C11 C12 C13 1.0(3) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 F16 -179.77(15) . . . . ?
C13 C14 C15 C10 0.8(3) . . . . ?
C11 C10 C15 F16 -179.83(14) . . . . ?
C8 C10 C15 F16 -1.1(2) . . . . ?
C11 C10 C15 C14 -0.4(2) . . . . ?
C8 C10 C15 C14 178.37(15) . . . . ?
C5 C6 N17 C18 41.3(2) . . . . ?
C7 C6 N17 C18 -141.67(15) . . . . ?
C6 N17 C18 O19 -4.3(3) . . . . ?
C6 N17 C18 O20 174.61(13) . . . . ?
O19 C18 O20 C21 4.9(2) . . . . ?
N17 C18 O20 C21 -173.97(14) . . . . ?
C18 O20 C21 C24 -63.0(2) . . . . ?
C18 O20 C21 C22 178.83(16) . . . . ?
C18 O20 C21 C23 61.5(2) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_NM049
_database_code_depnum_ccdc_archive 'CCDC 2204837'
loop_
_audit_author_name
_audit_author_address
'Thierry ROISNEL'
;Institut des Sciences Chimiques de Rennes
France
;
_audit_update_record             
;
2022-09-01 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 06 avril 2021                                            #
#------------------------------------------------------------------------------#


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H13 N S'
_chemical_formula_sum            'C21 H13 N S'
_chemical_formula_weight         311.38
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#


_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8473(9)
_cell_length_b                   9.7021(9)
_cell_length_c                   10.1837(10)
_cell_angle_alpha                66.774(3)
_cell_angle_beta                 69.333(4)
_cell_angle_gamma                77.281(3)
_cell_volume                     748.26(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2342
_cell_measurement_theta_min      2.2787
_cell_measurement_theta_max      27.3907
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.0049908
_diffrn_orient_matrix_UB_21      0.0543937
_diffrn_orient_matrix_UB_31      -0.1083251
_diffrn_orient_matrix_UB_12      0.1122662
_diffrn_orient_matrix_UB_22      -0.0089378
_diffrn_orient_matrix_UB_32      0.0021983
_diffrn_orient_matrix_UB_13      -0.0467800
_diffrn_orient_matrix_UB_23      -0.1010008
_diffrn_orient_matrix_UB_33      -0.0113625


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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             324
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_T_max  0.954

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

# Software                   : BIS 2014.5.0.0/23-May-2014 && APEX2_2014.11-0   #
# Number of scans            :        4                                        #
# Total number of frames     :      348                                        #
# Total length of scans      :   348.00 (deg.)                                 #
# Rotation speed             :    15.00 sec./deg.                              #
# Total exposition time      :      1 h  27.0 min.                             #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range  Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Omega   15.0  1.00    35.0   105  105.0   14.9   14.5  300.0  305.3 150.0 #
#  2 Omega   15.0  1.00    35.0   105  105.0   14.9   14.5   60.0  305.3 150.0 #
#  3 Omega   15.0  1.00    35.0   105  105.0   14.9   14.5  180.0  305.3 150.0 #
#  4 Omega   15.0  1.00    35.0    33   33.0   14.9   14.5    0.0  305.3 150.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.33
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_uneti/neti     0.0351
_diffrn_reflns_av_r_equivalents  0.0183
_diffrn_reflns_number            6171
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.294
_diffrn_reflns_theta_max         27.453
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.974
_reflns_number_total             3338
_reflns_number_gt                2620
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

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

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'

#------------------------------------------------------------------------------#
#                            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     
'w=1/[σ²(Fo²)+(0.1445P)²+2.5097P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3338
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1190
_refine_ls_R_factor_gt           0.0991
_refine_ls_wR_factor_ref         0.2889
_refine_ls_wR_factor_gt          0.2687
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         2.691
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.112

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.74837(14) 0.61410(12) 0.29250(12) 0.0349(4) Uani 1 1 d . . . . .
C1 C 0.6981(5) 0.4295(5) 0.3743(5) 0.0335(10) Uani 1 1 d . . . . .
C2 C 0.6584(5) 0.3506(6) 0.3006(5) 0.0360(10) Uani 1 1 d . . . . .
H2 H 0.654911 0.398832 0.200256 0.043 Uiso 1 1 calc R U . . .
C3 C 0.6255(6) 0.2047(6) 0.3773(6) 0.0405(11) Uani 1 1 d . . . . .
H3 H 0.600035 0.150634 0.328912 0.049 Uiso 1 1 calc R U . . .
C4 C 0.6283(6) 0.1333(6) 0.5228(6) 0.0397(11) Uani 1 1 d . . . . .
H4 H 0.604003 0.031394 0.573543 0.048 Uiso 1 1 calc R U . . .
C5 C 0.6653(5) 0.2071(5) 0.5947(5) 0.0300(9) Uani 1 1 d . . . . .
H5 H 0.666257 0.155647 0.695473 0.036 Uiso 1 1 calc R U . . .
C6 C 0.7023(4) 0.3572(4) 0.5241(4) 0.0236(8) Uani 1 1 d . . . . .
C7 C 0.7475(5) 0.4590(4) 0.5744(4) 0.0280(8) Uani 1 1 d . . . . .
C8 C 0.7649(5) 0.4410(5) 0.7085(5) 0.0297(9) Uani 1 1 d . . . . .
C9 C 0.7255(5) 0.2985(5) 0.8411(4) 0.0296(9) Uani 1 1 d . . . . .
C10 C 0.5722(5) 0.2892(5) 0.9417(5) 0.0338(10) Uani 1 1 d . . . . .
H10 H 0.492908 0.373063 0.927380 0.041 Uiso 1 1 calc R U . . .
C11 C 0.5328(5) 0.1582(5) 1.0639(5) 0.0327(9) Uani 1 1 d . . . . .
H11 H 0.426803 0.153132 1.132740 0.039 Uiso 1 1 calc R U . . .
C12 C 0.6465(5) 0.0353(5) 1.0861(4) 0.0305(9) Uani 1 1 d . . . . .
H12 H 0.619975 -0.053436 1.170954 0.037 Uiso 1 1 calc R U . . .
C13 C 0.7997(5) 0.0428(5) 0.9833(5) 0.0325(9) Uani 1 1 d . . . . .
H13 H 0.877983 -0.041941 0.996981 0.039 Uiso 1 1 calc R U . . .
C14 C 0.8396(5) 0.1735(5) 0.8603(5) 0.0367(10) Uani 1 1 d . . . . .
H14 H 0.944308 0.177484 0.789455 0.044 Uiso 1 1 calc R U . . .
C15 C 0.8172(4) 0.5645(4) 0.7211(4) 0.0245(8) Uani 1 1 d . . . . .
C16 C 0.8432(5) 0.5504(5) 0.8557(5) 0.0305(9) Uani 1 1 d . . . . .
H16 H 0.823778 0.459843 0.939634 0.037 Uiso 1 1 calc R U . . .
C17 C 0.8975(5) 0.6706(6) 0.8643(6) 0.0415(11) Uani 1 1 d . . . . .
H17 H 0.915296 0.663146 0.953634 0.050 Uiso 1 1 calc R U . . .
C18 C 0.9259(5) 0.8050(5) 0.7354(6) 0.0411(11) Uani 1 1 d . . . . .
H18 H 0.963062 0.887069 0.740189 0.049 Uiso 1 1 calc R U . . .
C19 C 0.9016(6) 0.8182(5) 0.6091(5) 0.0385(10) Uani 1 1 d . . . . .
H19 H 0.921526 0.909113 0.525672 0.046 Uiso 1 1 calc R U . . .
C20 C 0.8469(5) 0.6997(5) 0.5979(5) 0.0317(9) Uani 1 1 d . . . . .
N21 N 0.8258(4) 0.7252(5) 0.4622(4) 0.0406(10) Uani 1 1 d . . . . .
C22 C 0.7796(5) 0.6052(4) 0.4578(4) 0.0271(8) 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
S1 C1 1.735(5) . ?
S1 C22 1.766(4) . ?
C1 C6 1.416(6) . ?
C1 C2 1.426(7) . ?
C2 C3 1.359(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.372(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.358(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.401(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.454(6) . ?
C7 C8 1.367(6) . ?
C7 C22 1.454(5) . ?
C8 C15 1.440(6) . ?
C8 C9 1.505(5) . ?
C9 C10 1.377(6) . ?
C9 C14 1.393(6) . ?
C10 C11 1.388(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(6) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C20 1.409(5) . ?
C15 C16 1.419(6) . ?
C16 C17 1.398(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.431(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.330(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.398(7) . ?
C19 H19 0.9500 . ?
C20 N21 1.378(6) . ?
N21 C22 1.337(6) . ?

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
C1 S1 C22 91.2(2) . . ?
C6 C1 C2 120.5(4) . . ?
C6 C1 S1 114.8(4) . . ?
C2 C1 S1 124.7(3) . . ?
C3 C2 C1 118.4(4) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 121.8(4) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 120.5(4) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 121.7(4) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 117.1(4) . . ?
C5 C6 C7 132.3(4) . . ?
C1 C6 C7 110.6(4) . . ?
C8 C7 C22 116.0(4) . . ?
C8 C7 C6 131.8(4) . . ?
C22 C7 C6 112.3(4) . . ?
C7 C8 C15 118.1(4) . . ?
C7 C8 C9 121.3(4) . . ?
C15 C8 C9 120.7(4) . . ?
C10 C9 C14 119.4(4) . . ?
C10 C9 C8 119.5(4) . . ?
C14 C9 C8 121.0(4) . . ?
C9 C10 C11 120.5(4) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.5(4) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 119.3(4) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C12 C13 C14 120.5(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 119.8(4) . . ?
C13 C14 H14 120.1 . . ?
C9 C14 H14 120.1 . . ?
C20 C15 C16 119.3(4) . . ?
C20 C15 C8 120.1(4) . . ?
C16 C15 C8 120.6(4) . . ?
C17 C16 C15 119.6(4) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 118.5(4) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C19 C18 C17 121.9(4) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C18 C19 C20 120.7(4) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
N21 C20 C19 116.0(4) . . ?
N21 C20 C15 124.0(4) . . ?
C19 C20 C15 120.0(4) . . ?
C22 N21 C20 112.6(4) . . ?
N21 C22 C7 129.2(4) . . ?
N21 C22 S1 119.7(3) . . ?
C7 C22 S1 111.2(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 S1 C1 C6 0.2(3) . . . . ?
C22 S1 C1 C2 -178.4(4) . . . . ?
C6 C1 C2 C3 -0.3(6) . . . . ?
S1 C1 C2 C3 178.3(3) . . . . ?
C1 C2 C3 C4 0.7(7) . . . . ?
C2 C3 C4 C5 -0.4(7) . . . . ?
C3 C4 C5 C6 -0.2(7) . . . . ?
C4 C5 C6 C1 0.5(6) . . . . ?
C4 C5 C6 C7 -178.9(4) . . . . ?
C2 C1 C6 C5 -0.2(6) . . . . ?
S1 C1 C6 C5 -179.0(3) . . . . ?
C2 C1 C6 C7 179.3(4) . . . . ?
S1 C1 C6 C7 0.5(4) . . . . ?
C5 C6 C7 C8 -1.7(7) . . . . ?
C1 C6 C7 C8 178.9(4) . . . . ?
C5 C6 C7 C22 178.1(4) . . . . ?
C1 C6 C7 C22 -1.3(5) . . . . ?
C22 C7 C8 C15 -1.8(5) . . . . ?
C6 C7 C8 C15 178.0(4) . . . . ?
C22 C7 C8 C9 176.2(3) . . . . ?
C6 C7 C8 C9 -4.0(7) . . . . ?
C7 C8 C9 C10 -92.3(5) . . . . ?
C15 C8 C9 C10 85.6(5) . . . . ?
C7 C8 C9 C14 84.9(5) . . . . ?
C15 C8 C9 C14 -97.2(5) . . . . ?
C14 C9 C10 C11 2.0(7) . . . . ?
C8 C9 C10 C11 179.3(4) . . . . ?
C9 C10 C11 C12 -0.2(7) . . . . ?
C10 C11 C12 C13 -1.4(7) . . . . ?
C11 C12 C13 C14 1.0(7) . . . . ?
C12 C13 C14 C9 0.8(7) . . . . ?
C10 C9 C14 C13 -2.4(7) . . . . ?
C8 C9 C14 C13 -179.6(4) . . . . ?
C7 C8 C15 C20 0.8(6) . . . . ?
C9 C8 C15 C20 -177.2(4) . . . . ?
C7 C8 C15 C16 -177.6(4) . . . . ?
C9 C8 C15 C16 4.3(6) . . . . ?
C20 C15 C16 C17 0.1(6) . . . . ?
C8 C15 C16 C17 178.5(4) . . . . ?
C15 C16 C17 C18 -0.2(6) . . . . ?
C16 C17 C18 C19 0.2(7) . . . . ?
C17 C18 C19 C20 0.0(7) . . . . ?
C18 C19 C20 N21 -180.0(4) . . . . ?
C18 C19 C20 C15 -0.1(6) . . . . ?
C16 C15 C20 N21 179.9(4) . . . . ?
C8 C15 C20 N21 1.5(6) . . . . ?
C16 C15 C20 C19 0.0(6) . . . . ?
C8 C15 C20 C19 -178.4(4) . . . . ?
C19 C20 N21 C22 177.6(4) . . . . ?
C15 C20 N21 C22 -2.4(6) . . . . ?
C20 N21 C22 C7 1.2(6) . . . . ?
C20 N21 C22 S1 -179.2(3) . . . . ?
C8 C7 C22 N21 0.8(6) . . . . ?
C6 C7 C22 N21 -179.0(4) . . . . ?
C8 C7 C22 S1 -178.7(3) . . . . ?
C6 C7 C22 S1 1.4(4) . . . . ?
C1 S1 C22 N21 179.4(3) . . . . ?
C1 S1 C22 C7 -0.9(3) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_NM215F2_2
_database_code_depnum_ccdc_archive 'CCDC 2204833'
loop_
_audit_author_name
_audit_author_address
'Thierry ROISNEL'
;Institut des Sciences Chimiques de Rennes
France
;
_audit_update_record             
;
2022-09-01 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 29 juin 2022                                             #
#------------------------------------------------------------------------------#


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H7 Br Cl N O'
_chemical_formula_sum            'C12 H7 Br Cl N O'
_chemical_formula_weight         296.55
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration rm/ad/rmad/syn/unk/.

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
_space_group_IT_number           33
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   13.664(2)
_cell_length_b                   8.7402(15)
_cell_length_c                   18.815(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2247.0(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4999
_cell_measurement_theta_min      2.5695
_cell_measurement_theta_max      25.5483
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.0268156
_diffrn_orient_matrix_UB_21      -0.1033338
_diffrn_orient_matrix_UB_31      -0.0411543
_diffrn_orient_matrix_UB_12      0.0227229
_diffrn_orient_matrix_UB_22      0.0205708
_diffrn_orient_matrix_UB_32      -0.0664569
_diffrn_orient_matrix_UB_13      0.0489623
_diffrn_orient_matrix_UB_23      -0.0172472
_diffrn_orient_matrix_UB_33      0.0114025


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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.060
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1168
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    3.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.525
_exptl_absorpt_correction_T_max  0.793

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

# Software                   : BIS V6.2.15/2021-03-15 && APEX4 2021.10-0       #
# Number of scans            :        3                                        #
# Total number of frames [*] :      194                                        #
# Total length of scans  [*] :   194.00 (deg.)                                 #
# Rotation speed         [*] :    10.00 sec./deg.                              #
# Total exposition time  [*] :         32.3 min.                               #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Fast     1.0  1.00    34.0   180  180.0    0.0    0.0    0.0   54.7 150.0 #
#  2 Omega   10.0  1.00    34.0    97   97.0    0.1    2.7   72.0  -44.5 150.0 #
#  3 Omega   10.0  1.00    34.0    97   97.0    0.1    2.7    0.0  -44.5 150.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0730
_diffrn_reflns_av_r_equivalents  0.0684
_diffrn_reflns_number            16394
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.165
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_reflns_number_total             4810
_reflns_number_gt                3506
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.808
_reflns_Friedel_fraction_max     0.858
_reflns_Friedel_fraction_full    0.878

_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.
;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

#------------------------------------------------------------------------------#
#                            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     
'w=1/[σ²(Fo²)+(0.1105P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018_3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0116(18)
_refine_ls_number_reflns         4810
_refine_ls_number_parameters     293
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1784
_refine_ls_wR_factor_gt          0.1482
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.005
_refine_diff_density_max         0.810
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.159
_refine_ls_abs_structure_details 
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.03(4)

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

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
Br1 Br 0.62087(10) 0.59510(15) 0.25131(7) 0.0570(5) Uani 0.714(5) 1 d . . P A .
Cl1 Cl 0.62087(10) 0.59510(15) 0.25131(7) 0.0570(5) Uani 0.286(5) 1 d . . P A .
Cl11 Cl 0.34894(11) 0.62220(19) 0.35232(16) 0.0535(7) Uani 0.714(5) 1 d . . P A
.
Br11 Br 0.34894(11) 0.62220(19) 0.35232(16) 0.0535(7) Uani 0.286(5) 1 d . . P A
.
C1 C 0.6871(6) 0.4649(11) 0.3133(5) 0.039(2) Uani 1 1 d . . . . .
C2 C 0.7740(7) 0.4049(11) 0.2887(6) 0.048(2) Uani 0.714(5) 1 d . . P A 1
H2 H 0.799638 0.432135 0.243477 0.058 Uiso 0.714(5) 1 calc R U P A 1
N2 N 0.7740(7) 0.4049(11) 0.2887(6) 0.048(2) Uani 0.286(5) 1 d . . P A 2
C3 C 0.8230(6) 0.3015(12) 0.3335(6) 0.046(3) Uani 1 1 d . . . . .
H3 H 0.884907 0.262699 0.319305 0.055 Uiso 1 1 calc R U . A 1
C4 C 0.7843(8) 0.2551(12) 0.3967(9) 0.049(3) Uani 1 1 d . . . . .
H4 H 0.817202 0.181391 0.425153 0.059 Uiso 1 1 calc R U . . .
C5 C 0.6963(6) 0.3173(10) 0.4187(6) 0.039(2) Uani 1 1 d . . . . .
H5 H 0.668651 0.285855 0.462695 0.047 Uiso 1 1 calc R U . . .
C6 C 0.6478(6) 0.4255(9) 0.3775(5) 0.0335(19) Uani 1 1 d . . . . .
C7 C 0.5525(5) 0.4865(10) 0.4068(5) 0.0329(19) Uani 1 1 d . . . . .
O8 O 0.4938(4) 0.3982(7) 0.4333(4) 0.0449(17) Uani 1 1 d . . . . .
C9 C 0.5380(6) 0.6558(10) 0.4070(5) 0.0339(19) Uani 1 1 d . . . . .
C10 C 0.4491(7) 0.7265(11) 0.3908(8) 0.040(2) Uani 1 1 d . . . . .
N11 N 0.4346(7) 0.8783(9) 0.3969(6) 0.045(2) Uani 0.714(5) 1 d . . P A 1
C11 C 0.4346(7) 0.8783(9) 0.3969(6) 0.045(2) Uani 0.286(5) 1 d . . P A 2
H11 H 0.373337 0.922815 0.385007 0.054 Uiso 0.286(5) 1 calc R U P A 2
C12 C 0.5102(9) 0.9662(12) 0.4205(6) 0.051(3) Uani 1 1 d . . . . .
H12 H 0.500557 1.073228 0.425954 0.062 Uiso 1 1 calc R U . A 1
C13 C 0.6002(9) 0.9044(12) 0.4367(7) 0.050(3) Uani 1 1 d . . . . .
H13 H 0.652278 0.968463 0.451881 0.060 Uiso 1 1 calc R U . . .
C14 C 0.6139(7) 0.7486(11) 0.4306(9) 0.044(3) Uani 1 1 d . . . . .
H14 H 0.675331 0.704762 0.442566 0.053 Uiso 1 1 calc R U . . .
Br2 Br 0.88255(9) 0.59907(14) 0.75011(7) 0.0533(5) Uani 0.681(6) 1 d . . P B .
Cl2 Cl 0.88255(9) 0.59907(14) 0.75011(7) 0.0533(5) Uani 0.319(6) 1 d . . P B .
Cl12 Cl 0.60512(11) 0.6359(2) 0.64901(15) 0.0543(7) Uani 0.681(6) 1 d . . P B .
Br12 Br 0.60512(11) 0.6359(2) 0.64901(15) 0.0543(7) Uani 0.319(6) 1 d . . P B .
C21 C 0.9458(7) 0.4655(10) 0.6872(5) 0.041(2) Uani 1 1 d . . . . .
C22 C 1.0304(7) 0.4015(11) 0.7116(6) 0.047(2) Uani 0.681(6) 1 d . . P B 1
H22 H 1.056453 0.426860 0.756906 0.056 Uiso 0.681(6) 1 calc R U P B 1
N22 N 1.0304(7) 0.4015(11) 0.7116(6) 0.047(2) Uani 0.319(6) 1 d . . P B 2
C23 C 1.0769(7) 0.2966(12) 0.6666(7) 0.048(3) Uani 1 1 d . . . . .
H23 H 1.138487 0.255103 0.679823 0.057 Uiso 1 1 calc R U . B 1
C24 C 1.0349(8) 0.2534(10) 0.6042(8) 0.043(3) Uani 1 1 d . . . . .
H24 H 1.065822 0.178612 0.575198 0.052 Uiso 1 1 calc R U . . .
C25 C 0.9487(6) 0.3173(10) 0.5832(6) 0.036(2) Uani 1 1 d . . . . .
H25 H 0.919434 0.285155 0.539857 0.044 Uiso 1 1 calc R U . . .
C26 C 0.9033(6) 0.4275(9) 0.6236(5) 0.0325(18) Uani 1 1 d . . . . .
C27 C 0.8082(6) 0.4933(11) 0.5978(5) 0.036(2) Uani 1 1 d . . . . .
O28 O 0.7451(4) 0.4073(7) 0.5758(5) 0.0465(18) Uani 1 1 d . . . . .
C29 C 0.7966(5) 0.6620(10) 0.5943(5) 0.0336(19) Uani 1 1 d . . . . .
C30 C 0.7098(7) 0.7401(11) 0.6112(7) 0.036(2) Uani 1 1 d . . . . .
N31 N 0.6971(6) 0.8909(10) 0.6047(6) 0.049(2) Uani 0.681(6) 1 d . . P B 1
C31 C 0.6971(6) 0.8909(10) 0.6047(6) 0.049(2) Uani 0.319(6) 1 d . . P B 2
H31 H 0.637171 0.938836 0.617170 0.058 Uiso 0.319(6) 1 calc R U P B 2
C32 C 0.7719(8) 0.9699(12) 0.5800(6) 0.047(2) Uani 1 1 d . . . . .
H32 H 0.763769 1.077192 0.574332 0.056 Uiso 1 1 calc R U . B 1
C33 C 0.8601(8) 0.9085(11) 0.5621(7) 0.045(2) Uani 1 1 d . . . . .
H33 H 0.911799 0.970640 0.544524 0.054 Uiso 1 1 calc R U . . .
C34 C 0.8718(6) 0.7499(10) 0.5705(8) 0.038(3) Uani 1 1 d . . . . .
H34 H 0.932793 0.703567 0.559374 0.046 Uiso 1 1 calc R U . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.864(10) . ?
Br11 C10 1.797(11) . ?
C1 C6 1.365(14) . ?
C1 N2 1.379(12) . ?
C1 C2 1.379(12) . ?
C2 C3 1.406(16) . ?
C2 H2 0.9500 . ?
N2 C3 1.406(16) . ?
C3 C4 1.363(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(14) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(13) . ?
C5 H5 0.9500 . ?
C6 C7 1.511(11) . ?
C7 O8 1.220(11) . ?
C7 C9 1.492(12) . ?
C9 C14 1.390(13) . ?
C9 C10 1.397(13) . ?
C10 C11 1.346(13) . ?
C10 N11 1.346(13) . ?
N11 C12 1.362(15) . ?
C11 C12 1.362(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(14) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
Br2 C21 1.874(10) . ?
Br12 C30 1.839(11) . ?
C21 N22 1.364(13) . ?
C21 C22 1.364(13) . ?
C21 C26 1.370(14) . ?
C22 C23 1.401(15) . ?
C22 H22 0.9500 . ?
N22 C23 1.401(15) . ?
C23 C24 1.360(19) . ?
C23 H23 0.9500 . ?
C24 C25 1.363(14) . ?
C24 H24 0.9500 . ?
C25 C26 1.375(12) . ?
C25 H25 0.9500 . ?
C26 C27 1.502(12) . ?
C27 O28 1.217(10) . ?
C27 C29 1.485(13) . ?
C29 C34 1.359(12) . ?
C29 C30 1.404(13) . ?
C30 C31 1.334(13) . ?
C30 N31 1.334(13) . ?
N31 C32 1.318(14) . ?
C31 C32 1.318(14) . ?
C31 H31 0.9500 . ?
C32 C33 1.361(14) . ?
C32 H32 0.9500 . ?
C33 C34 1.405(13) . ?
C33 H33 0.9500 . ?
C34 H34 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
C6 C1 N2 122.7(9) . . ?
C6 C1 C2 122.7(9) . . ?
C6 C1 Br1 121.1(6) . . ?
N2 C1 Br1 116.1(8) . . ?
C2 C1 Br1 116.1(8) . . ?
C1 C2 C3 116.9(10) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 H2 121.5 . . ?
C1 N2 C3 116.9(10) . . ?
C4 C3 C2 122.0(9) . . ?
C4 C3 N2 122.0(9) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 118.7(11) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 121.0(11) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.5(8) . . ?
C1 C6 C7 124.9(8) . . ?
C5 C6 C7 116.5(9) . . ?
O8 C7 C9 122.6(8) . . ?
O8 C7 C6 119.5(8) . . ?
C9 C7 C6 117.8(7) . . ?
C14 C9 C10 117.4(9) . . ?
C14 C9 C7 118.7(8) . . ?
C10 C9 C7 123.6(8) . . ?
C11 C10 C9 123.1(10) . . ?
N11 C10 C9 123.1(10) . . ?
C11 C10 Br11 114.9(8) . . ?
N11 C10 Br11 114.9(8) . . ?
C9 C10 Br11 121.7(8) . . ?
C10 N11 C12 118.2(9) . . ?
C10 C11 C12 118.2(9) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
C11 C12 C13 121.8(9) . . ?
N11 C12 C13 121.8(9) . . ?
N11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C12 C13 C14 119.4(10) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C9 120.1(10) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
N22 C21 C26 123.7(9) . . ?
C22 C21 C26 123.7(9) . . ?
N22 C21 Br2 115.7(8) . . ?
C22 C21 Br2 115.7(8) . . ?
C26 C21 Br2 120.5(7) . . ?
C21 C22 C23 116.7(10) . . ?
C21 C22 H22 121.7 . . ?
C23 C22 H22 121.7 . . ?
C21 N22 C23 116.7(10) . . ?
C24 C23 C22 120.9(9) . . ?
C24 C23 N22 120.9(9) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 C23 120.1(11) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 121.1(10) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.4 . . ?
C21 C26 C25 117.5(8) . . ?
C21 C26 C27 123.8(8) . . ?
C25 C26 C27 118.7(9) . . ?
O28 C27 C29 121.5(8) . . ?
O28 C27 C26 119.1(8) . . ?
C29 C27 C26 119.2(7) . . ?
C34 C29 C30 116.0(9) . . ?
C34 C29 C27 119.7(7) . . ?
C30 C29 C27 124.3(8) . . ?
C31 C30 C29 124.7(10) . . ?
N31 C30 C29 124.7(10) . . ?
C31 C30 Br12 115.1(8) . . ?
N31 C30 Br12 115.1(8) . . ?
C29 C30 Br12 120.2(7) . . ?
C32 N31 C30 116.7(9) . . ?
C32 C31 C30 116.7(9) . . ?
C32 C31 H31 121.7 . . ?
C30 C31 H31 121.7 . . ?
C31 C32 C33 124.5(9) . . ?
N31 C32 C33 124.5(9) . . ?
N31 C32 H32 117.7 . . ?
C33 C32 H32 117.7 . . ?
C32 C33 C34 117.5(9) . . ?
C32 C33 H33 121.2 . . ?
C34 C33 H33 121.3 . . ?
C29 C34 C33 120.6(9) . . ?
C29 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.3(14) . . . . ?
Br1 C1 C2 C3 -177.4(7) . . . . ?
C6 C1 N2 C3 -1.3(14) . . . . ?
Br1 C1 N2 C3 -177.4(7) . . . . ?
C1 C2 C3 C4 3.7(16) . . . . ?
C1 N2 C3 C4 3.7(16) . . . . ?
C2 C3 C4 C5 -3.0(17) . . . . ?
N2 C3 C4 C5 -3.0(17) . . . . ?
C3 C4 C5 C6 -0.1(16) . . . . ?
N2 C1 C6 C5 -1.6(14) . . . . ?
C2 C1 C6 C5 -1.6(14) . . . . ?
Br1 C1 C6 C5 174.4(7) . . . . ?
N2 C1 C6 C7 -179.5(9) . . . . ?
C2 C1 C6 C7 -179.5(9) . . . . ?
Br1 C1 C6 C7 -3.5(13) . . . . ?
C4 C5 C6 C1 2.3(14) . . . . ?
C4 C5 C6 C7 -179.7(9) . . . . ?
C1 C6 C7 O8 134.3(10) . . . . ?
C5 C6 C7 O8 -43.6(12) . . . . ?
C1 C6 C7 C9 -50.4(13) . . . . ?
C5 C6 C7 C9 131.7(9) . . . . ?
O8 C7 C9 C14 129.6(12) . . . . ?
C6 C7 C9 C14 -45.5(14) . . . . ?
O8 C7 C9 C10 -44.4(16) . . . . ?
C6 C7 C9 C10 140.4(10) . . . . ?
C14 C9 C10 C11 0.2(18) . . . . ?
C7 C9 C10 C11 174.3(11) . . . . ?
C14 C9 C10 N11 0.2(18) . . . . ?
C7 C9 C10 N11 174.3(11) . . . . ?
C14 C9 C10 Br11 174.3(10) . . . . ?
C7 C9 C10 Br11 -11.6(16) . . . . ?
C9 C10 N11 C12 -0.6(18) . . . . ?
Br11 C10 N11 C12 -175.0(8) . . . . ?
C9 C10 C11 C12 -0.6(18) . . . . ?
Br11 C10 C11 C12 -175.0(8) . . . . ?
C10 C11 C12 C13 1.3(17) . . . . ?
C10 N11 C12 C13 1.3(17) . . . . ?
C11 C12 C13 C14 -1.6(19) . . . . ?
N11 C12 C13 C14 -1.6(19) . . . . ?
C12 C13 C14 C9 1(2) . . . . ?
C10 C9 C14 C13 -0.6(19) . . . . ?
C7 C9 C14 C13 -175.0(12) . . . . ?
C26 C21 C22 C23 3.0(15) . . . . ?
Br2 C21 C22 C23 177.5(7) . . . . ?
C26 C21 N22 C23 3.0(15) . . . . ?
Br2 C21 N22 C23 177.5(7) . . . . ?
C21 C22 C23 C24 -4.8(15) . . . . ?
C21 N22 C23 C24 -4.8(15) . . . . ?
C22 C23 C24 C25 2.9(16) . . . . ?
N22 C23 C24 C25 2.9(16) . . . . ?
C23 C24 C25 C26 1.0(14) . . . . ?
N22 C21 C26 C25 0.7(14) . . . . ?
C22 C21 C26 C25 0.7(14) . . . . ?
Br2 C21 C26 C25 -173.6(7) . . . . ?
N22 C21 C26 C27 177.6(9) . . . . ?
C22 C21 C26 C27 177.6(9) . . . . ?
Br2 C21 C26 C27 3.2(12) . . . . ?
C24 C25 C26 C21 -2.8(13) . . . . ?
C24 C25 C26 C27 -179.8(8) . . . . ?
C21 C26 C27 O28 -131.1(10) . . . . ?
C25 C26 C27 O28 45.7(12) . . . . ?
C21 C26 C27 C29 53.9(12) . . . . ?
C25 C26 C27 C29 -129.3(9) . . . . ?
O28 C27 C29 C34 -133.8(11) . . . . ?
C26 C27 C29 C34 41.0(14) . . . . ?
O28 C27 C29 C30 43.0(15) . . . . ?
C26 C27 C29 C30 -142.1(10) . . . . ?
C34 C29 C30 C31 0.6(18) . . . . ?
C27 C29 C30 C31 -176.3(11) . . . . ?
C34 C29 C30 N31 0.6(18) . . . . ?
C27 C29 C30 N31 -176.3(11) . . . . ?
C34 C29 C30 Br12 -176.4(10) . . . . ?
C27 C29 C30 Br12 6.7(15) . . . . ?
C29 C30 N31 C32 0.6(19) . . . . ?
Br12 C30 N31 C32 177.7(8) . . . . ?
C29 C30 C31 C32 0.6(19) . . . . ?
Br12 C30 C31 C32 177.7(8) . . . . ?
C30 C31 C32 C33 -1.0(18) . . . . ?
C30 N31 C32 C33 -1.0(18) . . . . ?
C31 C32 C33 C34 0.1(19) . . . . ?
N31 C32 C33 C34 0.1(19) . . . . ?
C30 C29 C34 C33 -1.5(18) . . . . ?
C27 C29 C34 C33 175.6(11) . . . . ?
C32 C33 C34 C29 1(2) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


