# Electronic Supplementary Material (ESI) for Organic .
# This journal is © The Royal Society of Chemistry 2014

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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H23 F N2'
_chemical_formula_weight         394.47

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   10.764(3)
_cell_length_b                   12.052(4)
_cell_length_c                   17.532(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.151(7)
_cell_angle_gamma                90.00
_cell_volume                     2173.2(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1936
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      22.70

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9804
_exptl_absorpt_correction_T_max  0.9849
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10906
_diffrn_reflns_av_R_equivalents  0.0808
_diffrn_reflns_av_sigmaI/netI    0.1317
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3793
_reflns_number_gt                2115
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         3793
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1725
_refine_ls_R_factor_gt           0.1100
_refine_ls_wR_factor_ref         0.3547
_refine_ls_wR_factor_gt          0.2706
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 1.5169(3) 0.0413(3) 0.0852(2) 0.1011(11) Uani 1 1 d . . .
N3 N 0.6127(3) 0.4248(3) 0.1093(2) 0.0573(10) Uani 1 1 d . . .
N4 N 0.8015(3) 0.2371(3) 0.1921(2) 0.0525(9) Uani 1 1 d . . .
C1 C 0.7075(4) 0.5919(4) 0.1045(2) 0.0583(11) Uani 1 1 d . . .
C2 C 0.7111(5) 0.7064(4) 0.1026(3) 0.0818(16) Uani 1 1 d . . .
H2 H 0.7864 0.7434 0.1014 0.098 Uiso 1 1 calc R . .
C3 C 0.6010(6) 0.7648(5) 0.1024(4) 0.0924(18) Uani 1 1 d . . .
H3 H 0.6033 0.8419 0.1041 0.111 Uiso 1 1 calc R . .
C4 C 0.4863(5) 0.7093(5) 0.0997(4) 0.0877(17) Uani 1 1 d . . .
H4 H 0.4116 0.7506 0.0956 0.105 Uiso 1 1 calc R . .
C5 C 0.4798(5) 0.5985(4) 0.1027(3) 0.0730(14) Uani 1 1 d . . .
H5 H 0.4034 0.5633 0.1037 0.088 Uiso 1 1 calc R . .
C6 C 0.5914(4) 0.5367(4) 0.1045(2) 0.0572(11) Uani 1 1 d . . .
C8 C 0.7404(4) 0.4060(3) 0.1120(2) 0.0562(11) Uani 1 1 d . . .
C7 C 0.7996(4) 0.5045(4) 0.1088(3) 0.0609(12) Uani 1 1 d . . .
H7 H 0.8856 0.5138 0.1093 0.073 Uiso 1 1 calc R . .
C9 C 0.5161(5) 0.3439(4) 0.1123(3) 0.0758(15) Uani 1 1 d . . .
H9A H 0.5185 0.3317 0.1668 0.114 Uiso 1 1 calc R . .
H9B H 0.5336 0.2755 0.0894 0.114 Uiso 1 1 calc R . .
H9C H 0.4316 0.3706 0.0827 0.114 Uiso 1 1 calc R . .
C10 C 0.7958(5) 0.2921(4) 0.1168(3) 0.0616(12) Uani 1 1 d . . .
H10A H 0.7429 0.2480 0.0729 0.074 Uiso 1 1 calc R . .
H10B H 0.8828 0.2962 0.1114 0.074 Uiso 1 1 calc R . .
C11 C 0.8966(4) 0.2868(3) 0.2609(3) 0.0589(12) Uani 1 1 d . . .
H11A H 0.8906 0.3671 0.2573 0.071 Uiso 1 1 calc R . .
H11B H 0.9837 0.2654 0.2613 0.071 Uiso 1 1 calc R . .
C12 C 0.8717(5) 0.2491(4) 0.3360(3) 0.0638(12) Uani 1 1 d . . .
H12A H 0.7938 0.2849 0.3409 0.077 Uiso 1 1 calc R . .
H12B H 0.9438 0.2714 0.3812 0.077 Uiso 1 1 calc R . .
C13 C 0.8549(4) 0.1238(4) 0.3378(3) 0.0531(11) Uani 1 1 d . . .
C14 C 0.8611(5) 0.0686(4) 0.4082(3) 0.0662(12) Uani 1 1 d . . .
H14 H 0.8767 0.1089 0.4554 0.079 Uiso 1 1 calc R . .
C15 C 0.8445(5) -0.0449(5) 0.4099(3) 0.0752(14) Uani 1 1 d . . .
H15 H 0.8489 -0.0804 0.4577 0.090 Uiso 1 1 calc R . .
C16 C 0.8216(5) -0.1049(4) 0.3411(4) 0.0753(15) Uani 1 1 d . . .
H16 H 0.8097 -0.1813 0.3419 0.090 Uiso 1 1 calc R . .
C17 C 0.8161(4) -0.0520(4) 0.2703(3) 0.0682(13) Uani 1 1 d . . .
H17 H 0.8016 -0.0934 0.2237 0.082 Uiso 1 1 calc R . .
C18 C 0.8322(4) 0.0635(3) 0.2678(3) 0.0517(10) Uani 1 1 d . . .
C19 C 0.8273(4) 0.1190(3) 0.1894(3) 0.0518(11) Uani 1 1 d . . .
H19 H 0.7535 0.0866 0.1486 0.062 Uiso 1 1 calc R . .
C20 C 0.9466(4) 0.0930(4) 0.1658(3) 0.0597(12) Uani 1 1 d . . .
C21 C 1.0439(4) 0.0797(3) 0.1478(3) 0.0583(12) Uani 1 1 d . . .
C22 C 1.1653(4) 0.0672(3) 0.1300(3) 0.0525(11) Uani 1 1 d . . .
C27 C 1.1716(6) 0.0550(6) 0.0548(4) 0.0939(19) Uani 1 1 d . . .
H27 H 1.0953 0.0540 0.0126 0.113 Uiso 1 1 calc R . .
C26 C 1.2907(6) 0.0437(6) 0.0393(4) 0.100(2) Uani 1 1 d . . .
H26 H 1.2942 0.0335 -0.0126 0.120 Uiso 1 1 calc R . .
C25 C 1.4002(5) 0.0480(4) 0.1006(3) 0.0660(13) Uani 1 1 d . . .
C24 C 1.3982(5) 0.0597(6) 0.1766(4) 0.100(2) Uani 1 1 d . . .
H24 H 1.4751 0.0608 0.2185 0.120 Uiso 1 1 calc R . .
C23 C 1.2795(5) 0.0701(6) 0.1908(3) 0.096(2) Uani 1 1 d . . .
H23 H 1.2769 0.0794 0.2430 0.115 Uiso 1 1 calc R . .


_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 C25 1.362(5) . ?
N3 C6 1.367(5) . ?
N3 C8 1.381(5) . ?
N3 C9 1.437(5) . ?
N4 C10 1.462(6) . ?
N4 C19 1.454(5) . ?
N4 C11 1.461(5) . ?
C1 C2 1.382(7) . ?
C1 C6 1.415(6) . ?
C1 C7 1.433(6) . ?
C2 C3 1.378(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.339(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.406(6) . ?
C5 H5 0.9300 . ?
C8 C7 1.356(6) . ?
C8 C10 1.489(6) . ?
C7 H7 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.489(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.522(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.387(6) . ?
C13 C18 1.385(6) . ?
C14 C15 1.381(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.365(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.405(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.516(6) . ?
C19 C20 1.495(6) . ?
C19 H19 0.9800 . ?
C20 C21 1.191(6) . ?
C21 C22 1.437(6) . ?
C22 C27 1.349(7) . ?
C22 C23 1.370(7) . ?
C27 C26 1.393(7) . ?
C27 H27 0.9300 . ?
C26 C25 1.342(8) . ?
C26 H26 0.9300 . ?
C25 C24 1.347(8) . ?
C24 C23 1.378(7) . ?
C24 H24 0.9300 . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N3 C8 108.1(3) . . ?
C6 N3 C9 124.2(4) . . ?
C8 N3 C9 127.7(4) . . ?
C10 N4 C19 111.8(3) . . ?
C10 N4 C11 113.1(3) . . ?
C19 N4 C11 109.5(3) . . ?
C2 C1 C6 120.0(4) . . ?
C2 C1 C7 135.3(4) . . ?
C6 C1 C7 104.6(4) . . ?
C1 C2 C3 118.7(5) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 120.6(5) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 122.3(5) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C4 C5 C6 118.3(5) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
N3 C6 C1 109.4(4) . . ?
N3 C6 C5 130.6(4) . . ?
C1 C6 C5 120.0(4) . . ?
C7 C8 N3 109.3(4) . . ?
C7 C8 C10 128.6(4) . . ?
N3 C8 C10 122.1(4) . . ?
C8 C7 C1 108.6(4) . . ?
C8 C7 H7 125.7 . . ?
C1 C7 H7 125.7 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C10 C8 112.2(4) . . ?
N4 C10 H10A 109.2 . . ?
C8 C10 H10A 109.2 . . ?
N4 C10 H10B 109.2 . . ?
C8 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
N4 C11 C12 109.8(4) . . ?
N4 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
N4 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C11 C12 C13 112.1(3) . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C18 119.1(4) . . ?
C14 C13 C12 121.4(4) . . ?
C18 C13 C12 119.6(4) . . ?
C13 C14 C15 121.4(5) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 119.8(5) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 119.9(4) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 120.8(4) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C13 C18 C17 119.0(4) . . ?
C13 C18 C19 121.4(4) . . ?
C17 C18 C19 119.6(4) . . ?
N4 C19 C20 113.7(3) . . ?
N4 C19 C18 111.0(3) . . ?
C20 C19 C18 110.9(3) . . ?
N4 C19 H19 107.0 . . ?
C20 C19 H19 107.0 . . ?
C18 C19 H19 107.0 . . ?
C21 C20 C19 175.5(4) . . ?
C20 C21 C22 176.8(5) . . ?
C27 C22 C23 118.1(5) . . ?
C27 C22 C21 122.3(4) . . ?
C23 C22 C21 119.6(4) . . ?
C22 C27 C26 121.1(5) . . ?
C22 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C25 C26 C27 118.8(5) . . ?
C25 C26 H26 120.6 . . ?
C27 C26 H26 120.6 . . ?
C24 C25 C26 122.0(5) . . ?
C24 C25 F1 119.1(5) . . ?
C26 C25 F1 118.9(5) . . ?
C25 C24 C23 118.4(5) . . ?
C25 C24 H24 120.8 . . ?
C23 C24 H24 120.8 . . ?
C22 C23 C24 121.6(5) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?

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
C6 C1 C2 C3 1.4(7) . . . . ?
C7 C1 C2 C3 -176.7(5) . . . . ?
C1 C2 C3 C4 -3.6(8) . . . . ?
C2 C3 C4 C5 4.8(9) . . . . ?
C3 C4 C5 C6 -3.4(8) . . . . ?
C8 N3 C6 C1 -0.3(5) . . . . ?
C9 N3 C6 C1 178.7(4) . . . . ?
C8 N3 C6 C5 -177.8(5) . . . . ?
C9 N3 C6 C5 1.2(7) . . . . ?
C2 C1 C6 N3 -178.0(4) . . . . ?
C7 C1 C6 N3 0.6(5) . . . . ?
C2 C1 C6 C5 -0.2(7) . . . . ?
C7 C1 C6 C5 178.4(4) . . . . ?
C4 C5 C6 N3 178.4(5) . . . . ?
C4 C5 C6 C1 1.2(7) . . . . ?
C6 N3 C8 C7 -0.1(5) . . . . ?
C9 N3 C8 C7 -179.1(4) . . . . ?
C6 N3 C8 C10 -179.6(4) . . . . ?
C9 N3 C8 C10 1.5(7) . . . . ?
N3 C8 C7 C1 0.5(5) . . . . ?
C10 C8 C7 C1 179.9(4) . . . . ?
C2 C1 C7 C8 177.6(5) . . . . ?
C6 C1 C7 C8 -0.7(5) . . . . ?
C19 N4 C10 C8 167.0(4) . . . . ?
C11 N4 C10 C8 -68.8(5) . . . . ?
C7 C8 C10 N4 114.7(5) . . . . ?
N3 C8 C10 N4 -65.9(5) . . . . ?
C10 N4 C11 C12 164.2(3) . . . . ?
C19 N4 C11 C12 -70.3(4) . . . . ?
N4 C11 C12 C13 48.7(5) . . . . ?
C11 C12 C13 C14 164.8(4) . . . . ?
C11 C12 C13 C18 -15.6(5) . . . . ?
C18 C13 C14 C15 -0.3(6) . . . . ?
C12 C13 C14 C15 179.3(4) . . . . ?
C13 C14 C15 C16 0.1(7) . . . . ?
C14 C15 C16 C17 0.5(7) . . . . ?
C15 C16 C17 C18 -0.8(7) . . . . ?
C14 C13 C18 C17 0.0(5) . . . . ?
C12 C13 C18 C17 -179.6(4) . . . . ?
C14 C13 C18 C19 -178.7(4) . . . . ?
C12 C13 C18 C19 1.7(5) . . . . ?
C16 C17 C18 C13 0.6(6) . . . . ?
C16 C17 C18 C19 179.3(4) . . . . ?
C10 N4 C19 C20 54.4(5) . . . . ?
C11 N4 C19 C20 -71.8(4) . . . . ?
C10 N4 C19 C18 -179.8(3) . . . . ?
C11 N4 C19 C18 54.1(4) . . . . ?
C13 C18 C19 N4 -20.7(5) . . . . ?
C17 C18 C19 N4 160.6(4) . . . . ?
C13 C18 C19 C20 106.7(4) . . . . ?
C17 C18 C19 C20 -72.0(5) . . . . ?
N4 C19 C20 C21 14(6) . . . . ?
C18 C19 C20 C21 -112(6) . . . . ?
C19 C20 C21 C22 48(12) . . . . ?
C20 C21 C22 C27 -153(8) . . . . ?
C20 C21 C22 C23 26(8) . . . . ?
C23 C22 C27 C26 1.1(9) . . . . ?
C21 C22 C27 C26 179.5(5) . . . . ?
C22 C27 C26 C25 -1.6(10) . . . . ?
C27 C26 C25 C24 1.8(10) . . . . ?
C27 C26 C25 F1 -177.5(5) . . . . ?
C26 C25 C24 C23 -1.5(10) . . . . ?
F1 C25 C24 C23 177.8(5) . . . . ?
C27 C22 C23 C24 -0.8(9) . . . . ?
C21 C22 C23 C24 -179.3(5) . . . . ?
C25 C24 C23 C22 1.0(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.126
_database_code_depnum_ccdc_archive 'CCDC 973071'
