# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_SX2_556P
_database_code_depnum_ccdc_archive 'CCDC 1553881'
_audit_update_record             
;
2017-06-02 deposited with the CCDC.
2017-10-11 downloaded from the CCDC.
;


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H13 F'
_chemical_formula_sum            'C24 H13 F'
_chemical_formula_weight         320.34
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                            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                   10.4684(7)
_cell_length_b                   7.4280(4)
_cell_length_c                   18.7773(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.086(3)
_cell_angle_gamma                90
_cell_volume                     1460.11(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    3463
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      27.50
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.045
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             664
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.092
_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  0.723
_exptl_absorpt_correction_T_max  0.996

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

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_ambient_temperature      150
_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_reflns_av_r_equivalents  0.0673
_diffrn_reflns_av_uneti/neti     0.0584
_diffrn_reflns_number            12886
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.363
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             3338
_reflns_number_gt                2348
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

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

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2017)'

#------------------------------------------------------------------------------#
#                            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)+(0.0668P)²+1.5977P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3338
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0647
_refine_ls_wR_factor_ref         0.1789
_refine_ls_wR_factor_gt          0.1592
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.062

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



# ............... End of .RES file .............................................



# ............... End of .HKL file .............................................
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#               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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3973(2) 0.1902(3) 0.46823(12) 0.0247(5) Uani 1 1 d . . . . .
C2 C 0.2835(2) 0.1289(3) 0.43615(13) 0.0332(6) Uani 1 1 d . . . . .
H2 H 0.284957 0.087315 0.388312 0.040 Uiso 1 1 calc R U . A 1
C3A C 0.1710(3) 0.1286(4) 0.47323(14) 0.0407(7) Uani 0.595(3) 1 d . . P B 1
H3A H 0.095246 0.087019 0.450655 0.049 Uiso 0.595(3) 1 calc R U P B 1
C3B C 0.1710(3) 0.1286(4) 0.47323(14) 0.0407(7) Uani 0.405(3) 1 d . . P B 2
F4 F 0.0652(4) 0.0799(7) 0.4415(2) 0.0558(7) Uani 0.405(3) 1 d . . P B 2
C5 C 0.1656(3) 0.1882(4) 0.54322(14) 0.0412(7) Uani 1 1 d . . . . .
H5 H 0.087139 0.185925 0.568525 0.049 Uiso 1 1 calc R U . B 1
C6 C 0.2748(2) 0.2505(3) 0.57564(13) 0.0315(6) Uani 1 1 d . . . . .
H6 H 0.270664 0.292199 0.623411 0.038 Uiso 1 1 calc R U . . .
C7 C 0.3928(2) 0.2539(3) 0.53953(11) 0.0235(5) Uani 1 1 d . . . . .
C8 C 0.5084(2) 0.3177(3) 0.57184(11) 0.0217(5) Uani 1 1 d . . . . .
C9 C 0.5305(2) 0.3956(3) 0.64362(11) 0.0230(5) Uani 1 1 d . . . . .
C10 C 0.4587(2) 0.4345(3) 0.70307(12) 0.0297(5) Uani 1 1 d . . . . .
H10 H 0.370590 0.404410 0.704526 0.036 Uiso 1 1 calc R U . . .
C11 C 0.5178(3) 0.5199(4) 0.76206(12) 0.0338(6) Uani 1 1 d . . . . .
H11 H 0.467190 0.546592 0.802667 0.041 Uiso 1 1 calc R U . . .
C12 C 0.6443(3) 0.5656(3) 0.76312(12) 0.0313(6) Uani 1 1 d . . . . .
H12 H 0.679862 0.624784 0.803392 0.038 Uiso 1 1 calc R U . . .
C13 C 0.7219(2) 0.5239(3) 0.70356(12) 0.0270(5) Uani 1 1 d . . . . .
C14 C 0.8546(3) 0.5588(3) 0.69658(13) 0.0346(6) Uani 1 1 d . . . . .
H14 H 0.899922 0.617417 0.733839 0.041 Uiso 1 1 calc R U . . .
C15 C 0.9168(3) 0.5076(4) 0.63598(14) 0.0408(7) Uani 1 1 d . . . . .
H15 H 1.006252 0.527921 0.632738 0.049 Uiso 1 1 calc R U . . .
C16 C 0.8531(2) 0.4252(4) 0.57756(14) 0.0359(6) Uani 1 1 d . . . . .
H16 H 0.899438 0.391923 0.536135 0.043 Uiso 1 1 calc R U . . .
C17 C 0.7238(2) 0.3941(3) 0.58151(12) 0.0248(5) Uani 1 1 d . . . . .
C18 C 0.6621(2) 0.4406(3) 0.64588(11) 0.0238(5) Uani 1 1 d . . . . .
C19 C 0.6227(2) 0.3190(3) 0.53485(11) 0.0227(5) Uani 1 1 d . . . . .
C20 C 0.6295(2) 0.2593(3) 0.46229(12) 0.0244(5) Uani 1 1 d . . . . .
C21 C 0.7431(2) 0.2681(4) 0.42199(13) 0.0338(6) Uani 1 1 d . . . . .
H21 H 0.818165 0.315117 0.443526 0.041 Uiso 1 1 calc R U . . .
C22 C 0.7480(3) 0.2110(4) 0.35283(14) 0.0415(7) Uani 1 1 d . . . . .
H22 H 0.824785 0.220393 0.326197 0.050 Uiso 1 1 calc R U . B 1
C23A C 0.6387(3) 0.1390(4) 0.32237(13) 0.0385(6) Uani 0.595(3) 1 d . . P B 1
F24 F 0.6447(3) 0.0784(5) 0.25537(14) 0.0558(7) Uani 0.595(3) 1 d . . P B 1
C23B C 0.6387(3) 0.1390(4) 0.32237(13) 0.0385(6) Uani 0.405(3) 1 d . . P B 2
H23B H 0.642451 0.094836 0.274945 0.046 Uiso 0.405(3) 1 calc R U P B 2
C25 C 0.5254(2) 0.1296(3) 0.35852(12) 0.0314(6) Uani 1 1 d . . . . .
H25 H 0.452022 0.080782 0.335804 0.038 Uiso 1 1 calc R U . B 1
C26 C 0.5171(2) 0.1920(3) 0.42931(11) 0.0239(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
C1 C2 1.409(3) . ?
C1 C7 1.421(3) . ?
C1 C26 1.452(3) . ?
C2 C3B 1.370(4) . ?
C2 C3A 1.370(4) . ?
C2 H2 0.9500 . ?
C3A C5 1.388(4) . ?
C3A H3A 0.9500 . ?
C3B F4 1.308(5) . ?
C3B C5 1.388(4) . ?
C5 C6 1.374(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.411(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.433(3) . ?
C8 C19 1.384(3) . ?
C8 C9 1.485(3) . ?
C9 C10 1.377(3) . ?
C9 C18 1.418(3) . ?
C10 C11 1.417(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.367(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.418(4) . ?
C12 H12 0.9500 . ?
C13 C18 1.395(3) . ?
C13 C14 1.420(4) . ?
C14 C15 1.366(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.422(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.375(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.414(3) . ?
C17 C19 1.482(3) . ?
C19 C20 1.435(3) . ?
C20 C21 1.411(3) . ?
C20 C26 1.420(3) . ?
C21 C22 1.367(3) . ?
C21 H21 0.9500 . ?
C22 C23B 1.386(4) . ?
C22 C23A 1.386(4) . ?
C22 H22 0.9500 . ?
C23A F24 1.338(4) . ?
C23A C25 1.369(4) . ?
C23B C25 1.369(4) . ?
C23B H23B 0.9500 . ?
C25 C26 1.410(3) . ?
C25 H25 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
C2 C1 C7 118.8(2) . . ?
C2 C1 C26 121.2(2) . . ?
C7 C1 C26 120.1(2) . . ?
C3B C2 C1 120.7(2) . . ?
C3A C2 C1 120.7(2) . . ?
C3A C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3A C5 121.1(2) . . ?
C2 C3A H3A 119.4 . . ?
C5 C3A H3A 119.4 . . ?
F4 C3B C2 119.8(3) . . ?
F4 C3B C5 119.0(3) . . ?
C2 C3B C5 121.1(2) . . ?
C6 C5 C3A 119.5(3) . . ?
C6 C5 C3B 119.5(3) . . ?
C6 C5 H5 120.3 . . ?
C3A C5 H5 120.3 . . ?
C5 C6 C7 121.4(2) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C6 C7 C1 118.5(2) . . ?
C6 C7 C8 122.8(2) . . ?
C1 C7 C8 118.7(2) . . ?
C19 C8 C7 121.3(2) . . ?
C19 C8 C9 108.60(19) . . ?
C7 C8 C9 130.1(2) . . ?
C10 C9 C18 117.2(2) . . ?
C10 C9 C8 137.1(2) . . ?
C18 C9 C8 105.61(19) . . ?
C9 C10 C11 119.3(2) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 122.9(2) . . ?
C12 C11 H11 118.5 . . ?
C10 C11 H11 118.5 . . ?
C11 C12 C13 119.4(2) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C18 C13 C12 116.9(2) . . ?
C18 C13 C14 116.6(2) . . ?
C12 C13 C14 126.5(2) . . ?
C15 C14 C13 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 122.6(2) . . ?
C14 C15 H15 118.7 . . ?
C16 C15 H15 118.7 . . ?
C17 C16 C15 119.4(2) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 117.1(2) . . ?
C16 C17 C19 137.2(2) . . ?
C18 C17 C19 105.71(19) . . ?
C13 C18 C17 124.6(2) . . ?
C13 C18 C9 124.2(2) . . ?
C17 C18 C9 111.21(19) . . ?
C8 C19 C20 121.2(2) . . ?
C8 C19 C17 108.84(19) . . ?
C20 C19 C17 129.9(2) . . ?
C21 C20 C26 118.7(2) . . ?
C21 C20 C19 122.5(2) . . ?
C26 C20 C19 118.7(2) . . ?
C22 C21 C20 121.9(2) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C21 C22 C23B 118.6(3) . . ?
C21 C22 C23A 118.6(3) . . ?
C21 C22 H22 120.7 . . ?
C23A C22 H22 120.7 . . ?
F24 C23A C25 119.4(3) . . ?
F24 C23A C22 118.5(3) . . ?
C25 C23A C22 122.0(2) . . ?
C25 C23B C22 122.0(2) . . ?
C25 C23B H23B 119.0 . . ?
C22 C23B H23B 119.0 . . ?
C23B C25 C26 120.4(2) . . ?
C23A C25 C26 120.4(2) . . ?
C23A C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C20 118.3(2) . . ?
C25 C26 C1 121.7(2) . . ?
C20 C26 C1 120.0(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C1 C2 C3B -0.8(4) . . . . ?
C26 C1 C2 C3B -179.7(2) . . . . ?
C7 C1 C2 C3A -0.8(4) . . . . ?
C26 C1 C2 C3A -179.7(2) . . . . ?
C1 C2 C3A C5 -0.1(4) . . . . ?
C1 C2 C3B F4 176.6(3) . . . . ?
C1 C2 C3B C5 -0.1(4) . . . . ?
C2 C3A C5 C6 0.8(4) . . . . ?
F4 C3B C5 C6 -175.9(4) . . . . ?
C2 C3B C5 C6 0.8(4) . . . . ?
C3A C5 C6 C7 -0.6(4) . . . . ?
C3B C5 C6 C7 -0.6(4) . . . . ?
C5 C6 C7 C1 -0.3(4) . . . . ?
C5 C6 C7 C8 -179.9(2) . . . . ?
C2 C1 C7 C6 1.0(3) . . . . ?
C26 C1 C7 C6 179.9(2) . . . . ?
C2 C1 C7 C8 -179.4(2) . . . . ?
C26 C1 C7 C8 -0.6(3) . . . . ?
C6 C7 C8 C19 179.9(2) . . . . ?
C1 C7 C8 C19 0.4(3) . . . . ?
C6 C7 C8 C9 -2.4(4) . . . . ?
C1 C7 C8 C9 178.0(2) . . . . ?
C19 C8 C9 C10 178.3(3) . . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
C19 C8 C9 C18 -0.2(2) . . . . ?
C7 C8 C9 C18 -178.0(2) . . . . ?
C18 C9 C10 C11 1.4(3) . . . . ?
C8 C9 C10 C11 -176.9(2) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C10 C11 C12 C13 -1.2(4) . . . . ?
C11 C12 C13 C18 1.4(3) . . . . ?
C11 C12 C13 C14 -178.8(2) . . . . ?
C18 C13 C14 C15 -1.2(3) . . . . ?
C12 C13 C14 C15 178.9(2) . . . . ?
C13 C14 C15 C16 2.2(4) . . . . ?
C14 C15 C16 C17 -0.3(4) . . . . ?
C15 C16 C17 C18 -2.5(4) . . . . ?
C15 C16 C17 C19 178.3(3) . . . . ?
C12 C13 C18 C17 178.1(2) . . . . ?
C14 C13 C18 C17 -1.7(3) . . . . ?
C12 C13 C18 C9 -0.2(3) . . . . ?
C14 C13 C18 C9 180.0(2) . . . . ?
C16 C17 C18 C13 3.6(3) . . . . ?
C19 C17 C18 C13 -176.9(2) . . . . ?
C16 C17 C18 C9 -177.9(2) . . . . ?
C19 C17 C18 C9 1.6(2) . . . . ?
C10 C9 C18 C13 -1.2(3) . . . . ?
C8 C9 C18 C13 177.6(2) . . . . ?
C10 C9 C18 C17 -179.7(2) . . . . ?
C8 C9 C18 C17 -0.9(2) . . . . ?
C7 C8 C19 C20 1.0(3) . . . . ?
C9 C8 C19 C20 -177.03(19) . . . . ?
C7 C8 C19 C17 179.21(19) . . . . ?
C9 C8 C19 C17 1.1(2) . . . . ?
C16 C17 C19 C8 177.6(3) . . . . ?
C18 C17 C19 C8 -1.7(2) . . . . ?
C16 C17 C19 C20 -4.4(4) . . . . ?
C18 C17 C19 C20 176.3(2) . . . . ?
C8 C19 C20 C21 176.5(2) . . . . ?
C17 C19 C20 C21 -1.2(4) . . . . ?
C8 C19 C20 C26 -2.3(3) . . . . ?
C17 C19 C20 C26 180.0(2) . . . . ?
C26 C20 C21 C22 -1.1(4) . . . . ?
C19 C20 C21 C22 -179.9(2) . . . . ?
C20 C21 C22 C23B -1.4(4) . . . . ?
C20 C21 C22 C23A -1.4(4) . . . . ?
C21 C22 C23A F24 -178.1(3) . . . . ?
C21 C22 C23A C25 2.4(4) . . . . ?
C21 C22 C23B C25 2.4(4) . . . . ?
C22 C23B C25 C26 -0.8(4) . . . . ?
F24 C23A C25 C26 179.7(3) . . . . ?
C22 C23A C25 C26 -0.8(4) . . . . ?
C23B C25 C26 C20 -1.8(3) . . . . ?
C23A C25 C26 C20 -1.8(3) . . . . ?
C23B C25 C26 C1 177.6(2) . . . . ?
C23A C25 C26 C1 177.6(2) . . . . ?
C21 C20 C26 C25 2.7(3) . . . . ?
C19 C20 C26 C25 -178.5(2) . . . . ?
C21 C20 C26 C1 -176.7(2) . . . . ?
C19 C20 C26 C1 2.1(3) . . . . ?
C2 C1 C26 C25 -1.2(3) . . . . ?
C7 C1 C26 C25 179.9(2) . . . . ?
C2 C1 C26 C20 178.2(2) . . . . ?
C7 C1 C26 C20 -0.7(3) . . . . ?

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR SX2_556P                                               #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_SX25_SP2
_database_code_depnum_ccdc_archive 'CCDC 1553883'
_audit_update_record             
;
2017-06-02 deposited with the CCDC.
2017-10-11 downloaded from the CCDC.
;


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H14 Cl2'
_chemical_formula_sum            'C24 H14 Cl2'
_chemical_formula_weight         373.25
_chemical_compound_source        'synthesis as described'

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


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
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'
'-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                   16.8237(12)
_cell_length_b                   11.3330(7)
_cell_length_c                   10.2994(8)
_cell_angle_alpha                90
_cell_angle_beta                 114.382(3)
_cell_angle_gamma                90
_cell_volume                     1788.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    2532
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      27.47
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             768
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.367
_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  0.838
_exptl_absorpt_correction_T_max  0.916

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

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150
_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_r_equivalents  0.0210
_diffrn_reflns_av_uneti/neti     0.0263
_diffrn_reflns_number            4736
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.479
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total             2048
_reflns_number_gt                1756
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

#------------------------------------------------------------------------------#
#                            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 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2017)'

#------------------------------------------------------------------------------#
#                            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)+(0.0422P)²+1.4346P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2048
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0828
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.052

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



# ............... End of .RES file .............................................



# ............... End of .HKL file .............................................
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#               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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.32828(8) 0.16558(11) 0.44358(15) 0.0203(3) Uani 1 1 d . . . . .
C2 C 0.34445(9) 0.26123(12) 0.37459(15) 0.0215(3) Uani 1 1 d . . . . .
H2 H 0.326399 0.260500 0.274177 0.026 Uiso 1 1 calc R U . . .
C3 C 0.38762(9) 0.35836(12) 0.45508(14) 0.0201(3) Uani 1 1 d . . . . .
H3 H 0.398624 0.424790 0.408671 0.024 Uiso 1 1 calc R U . . .
C4 C 0.41517(8) 0.36029(11) 0.60289(14) 0.0181(3) Uani 1 1 d . . . . .
C5 C 0.39573(8) 0.26281(12) 0.66821(14) 0.0201(3) Uani 1 1 d . . . . .
H5 H 0.412517 0.263489 0.768315 0.024 Uiso 1 1 calc R U . . .
C6 C 0.35247(9) 0.16547(12) 0.58942(15) 0.0211(3) Uani 1 1 d . . . . .
H6 H 0.339618 0.099715 0.634671 0.025 Uiso 1 1 calc R U . . .
C7 C 0.46354(9) 0.46293(11) 0.68616(14) 0.0182(3) Uani 1 1 d . . . . .
C8 C 0.43886(9) 0.58702(12) 0.64277(14) 0.0194(3) Uani 1 1 d . . . . .
C9 C 0.37326(9) 0.64179(13) 0.53047(15) 0.0240(3) Uani 1 1 d . . . . .
H9 H 0.329807 0.596977 0.457607 0.029 Uiso 1 1 calc R U . . .
C10 C 0.500000 0.65790(17) 0.750000 0.0195(4) Uani 1 2 d S T P . .
C11 C 0.500000 0.78079(17) 0.750000 0.0229(4) Uani 1 2 d S T P . .
C12 C 0.56703(10) 0.83550(13) 0.86939(17) 0.0274(3) Uani 1 1 d . . . . .
H12 H 0.569725 0.919084 0.876953 0.033 Uiso 1 1 calc R U . . .
C13 C 0.62801(10) 0.76743(13) 0.97401(16) 0.0281(3) Uani 1 1 d . . . . .
H13 H 0.672676 0.805752 1.052227 0.034 Uiso 1 1 calc R U . . .
Cl1 Cl 0.27588(2) 0.04204(3) 0.34336(4) 0.02943(13) Uani 1 1 d . . . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.383(2) . ?
C1 C6 1.385(2) . ?
C1 Cl1 1.7468(14) . ?
C2 C3 1.3890(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.3966(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.4005(19) . ?
C4 C7 1.4747(18) . ?
C5 C6 1.3848(19) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C7 1.379(3) 2_656 ?
C7 C8 1.4822(18) . ?
C8 C9 1.3737(19) . ?
C8 C10 1.4089(17) . ?
C9 C13 1.425(2) 2_656 ?
C9 H9 0.9500 . ?
C10 C11 1.393(3) . ?
C11 C12 1.4224(17) . ?
C11 C12 1.4224(17) 2_656 ?
C12 C13 1.377(2) . ?
C12 H12 0.9500 . ?
C13 H13 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
C2 C1 C6 121.73(12) . . ?
C2 C1 Cl1 118.87(11) . . ?
C6 C1 Cl1 119.40(10) . . ?
C1 C2 C3 118.66(13) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 121.29(13) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 118.23(12) . . ?
C3 C4 C7 120.09(12) . . ?
C5 C4 C7 121.67(12) . . ?
C6 C5 C4 121.16(13) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 C6 C5 118.88(12) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C7 C7 C4 127.92(7) 2_656 . ?
C7 C7 C8 108.40(7) 2_656 . ?
C4 C7 C8 123.67(11) . . ?
C9 C8 C10 118.37(13) . . ?
C9 C8 C7 135.25(13) . . ?
C10 C8 C7 106.36(12) . . ?
C8 C9 C13 118.36(14) . 2_656 ?
C8 C9 H9 120.8 . . ?
C13 C9 H9 120.8 2_656 . ?
C11 C10 C8 124.76(8) . 2_656 ?
C11 C10 C8 124.76(8) . . ?
C8 C10 C8 110.48(17) 2_656 . ?
C10 C11 C12 115.84(9) . . ?
C10 C11 C12 115.84(9) . 2_656 ?
C12 C11 C12 128.32(18) . 2_656 ?
C13 C12 C11 120.06(14) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C9 122.57(14) . 2_656 ?
C12 C13 H13 118.7 . . ?
C9 C13 H13 118.7 2_656 . ?

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 1.2(2) . . . . ?
Cl1 C1 C2 C3 -178.78(10) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C2 C3 C4 C5 -2.0(2) . . . . ?
C2 C3 C4 C7 177.88(12) . . . . ?
C3 C4 C5 C6 1.7(2) . . . . ?
C7 C4 C5 C6 -178.11(12) . . . . ?
C2 C1 C6 C5 -1.5(2) . . . . ?
Cl1 C1 C6 C5 178.55(10) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
C3 C4 C7 C7 -136.55(18) . . . 2_656 ?
C5 C4 C7 C7 43.3(2) . . . 2_656 ?
C3 C4 C7 C8 44.05(19) . . . . ?
C5 C4 C7 C8 -136.10(14) . . . . ?
C7 C7 C8 C9 -178.68(16) 2_656 . . . ?
C4 C7 C8 C9 0.8(2) . . . . ?
C7 C7 C8 C10 -0.10(17) 2_656 . . . ?
C4 C7 C8 C10 179.40(11) . . . . ?
C10 C8 C9 C13 1.91(19) . . . 2_656 ?
C7 C8 C9 C13 -179.65(15) . . . 2_656 ?
C9 C8 C10 C11 -1.10(14) . . . . ?
C7 C8 C10 C11 -179.96(6) . . . . ?
C9 C8 C10 C8 178.90(14) . . . 2_656 ?
C7 C8 C10 C8 0.04(6) . . . 2_656 ?
C8 C10 C11 C12 -0.68(10) 2_656 . . . ?
C8 C10 C11 C12 179.32(10) . . . . ?
C8 C10 C11 C12 179.32(10) 2_656 . . 2_656 ?
C8 C10 C11 C12 -0.68(10) . . . 2_656 ?
C10 C11 C12 C13 1.59(16) . . . . ?
C12 C11 C12 C13 -178.41(16) 2_656 . . . ?
C11 C12 C13 C9 -0.8(2) . . . 2_656 ?

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR SX25_SP2                                               #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
