# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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
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#  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_20130717aa_0m-sr

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H24 F N O2 S'
_chemical_formula_sum            'C21 H24 F N O2 S'
_chemical_formula_weight         373.47
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Hexagonal
_symmetry_space_group_name_H-M   'P6(5)   '
_symmetry_space_group_name_Hall  'P 65'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'

_cell_length_a                   16.1494(15)
_cell_length_b                   16.1494(15)
_cell_length_c                   15.1345(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     3418.3(5)
_cell_formula_units_Z            6
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7002
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      22.70

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.089
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1188
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9575
_exptl_absorpt_correction_T_max  0.9667
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            18924
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4008
_reflns_number_gt                3532
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.001 465 52 ' '
2 0.125 0.450 0.030 24 4 ' '
3 0.450 0.325 0.197 24 5 ' '
4 0.325 0.875 0.364 23 4 ' '
5 0.875 0.550 0.530 24 4 ' '
6 0.550 0.675 0.697 24 5 ' '
7 0.675 0.125 0.864 23 4 ' '
_platon_squeeze_details          
;
;

_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)+(0.0719P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_number_reflns         4008
_refine_ls_number_parameters     239
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.1016
_refine_ls_wR_factor_gt          0.0983
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.034
_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
C1 C 0.69884(16) 0.82884(16) -0.16813(15) 0.0666(5) Uani 1 1 d . . .
C2 C 0.7611(2) 0.8325(2) -0.23406(18) 0.0892(8) Uani 1 1 d . . .
H2 H 0.8017 0.8080 -0.2242 0.107 Uiso 1 1 calc R . .
C3 C 0.7611(3) 0.8728(3) -0.3132(2) 0.1243(13) Uani 1 1 d . . .
H3 H 0.8023 0.8768 -0.3580 0.149 Uiso 1 1 calc R . .
C4 C 0.6988(3) 0.9080(4) -0.3265(2) 0.1313(14) Uani 1 1 d . . .
H4 H 0.6993 0.9352 -0.3808 0.158 Uiso 1 1 calc R . .
C5 C 0.6367(2) 0.9040(3) -0.26214(19) 0.0994(9) Uani 1 1 d . . .
H5 H 0.5957 0.9277 -0.2725 0.119 Uiso 1 1 calc R . .
C6 C 0.63706(16) 0.86356(16) -0.18121(15) 0.0673(5) Uani 1 1 d . . .
C7 C 0.57597(17) 0.84897(18) -0.10124(15) 0.0679(6) Uani 1 1 d . . .
H7A H 0.5091 0.8057 -0.1144 0.081 Uiso 1 1 calc R . .
H7B H 0.5834 0.9093 -0.0811 0.081 Uiso 1 1 calc R . .
C8 C 0.61215(14) 0.80572(14) -0.03098(13) 0.0545(4) Uani 1 1 d . . .
H8 H 0.6457 0.8544 0.0146 0.065 Uiso 1 1 calc R . .
C9 C 0.68645(15) 0.78931(16) -0.07936(15) 0.0616(5) Uani 1 1 d . . .
C10 C 0.53375(13) 0.71436(13) 0.01533(11) 0.0516(4) Uani 1 1 d . . .
C11 C 0.49104(18) 0.63088(17) -0.05010(17) 0.0773(6) Uani 1 1 d . . .
H11A H 0.5391 0.6155 -0.0670 0.116 Uiso 1 1 calc R . .
H11B H 0.4687 0.6486 -0.1016 0.116 Uiso 1 1 calc R . .
H11C H 0.4385 0.5762 -0.0228 0.116 Uiso 1 1 calc R . .
C12 C 0.45914(13) 0.73421(13) 0.05725(13) 0.0527(4) Uani 1 1 d . . .
C13 C 0.36244(15) 0.67867(18) 0.03858(16) 0.0700(6) Uani 1 1 d . . .
H13 H 0.3422 0.6303 -0.0033 0.084 Uiso 1 1 calc R . .
C14 C 0.29578(18) 0.6941(2) 0.0812(2) 0.0896(8) Uani 1 1 d . . .
H14 H 0.2309 0.6561 0.0690 0.108 Uiso 1 1 calc R . .
C15 C 0.32668(19) 0.7652(2) 0.14089(17) 0.0802(7) Uani 1 1 d . . .
C16 C 0.42144(18) 0.82376(18) 0.16172(15) 0.0709(6) Uani 1 1 d . . .
H16 H 0.4406 0.8726 0.2031 0.085 Uiso 1 1 calc R . .
C17 C 0.48710(15) 0.80688(15) 0.11850(14) 0.0585(5) Uani 1 1 d . . .
H17 H 0.5518 0.8455 0.1310 0.070 Uiso 1 1 calc R . .
C18 C 0.61318(16) 0.64693(15) 0.24688(14) 0.0625(5) Uani 1 1 d . . .
C19 C 0.70174(17) 0.6501(2) 0.2090(2) 0.0869(8) Uani 1 1 d . . .
H19A H 0.7320 0.7021 0.1679 0.130 Uiso 1 1 calc R . .
H19B H 0.6838 0.5910 0.1793 0.130 Uiso 1 1 calc R . .
H19C H 0.7454 0.6592 0.2561 0.130 Uiso 1 1 calc R . .
C20 C 0.6317(2) 0.7423(2) 0.28252(18) 0.0875(7) Uani 1 1 d . . .
H20A H 0.6644 0.7547 0.3381 0.131 Uiso 1 1 calc R . .
H20B H 0.5720 0.7406 0.2907 0.131 Uiso 1 1 calc R . .
H20C H 0.6705 0.7919 0.2414 0.131 Uiso 1 1 calc R . .
C21 C 0.5661(2) 0.5686(2) 0.31699(19) 0.0916(8) Uani 1 1 d . . .
H21A H 0.6094 0.5826 0.3655 0.137 Uiso 1 1 calc R . .
H21B H 0.5508 0.5080 0.2916 0.137 Uiso 1 1 calc R . .
H21C H 0.5087 0.5659 0.3378 0.137 Uiso 1 1 calc R . .
F1 F 0.26076(14) 0.78094(18) 0.18305(13) 0.1303(7) Uani 1 1 d . . .
N1 N 0.58520(11) 0.69722(11) 0.08867(10) 0.0527(4) Uani 1 1 d . . .
H1A H 0.6288 0.6948 0.0687 0.063 Uiso 1 1 d R . .
O1 O 0.72685(14) 0.74904(14) -0.04837(13) 0.0874(5) Uani 1 1 d . . .
O2 O 0.50253(15) 0.51673(11) 0.12829(13) 0.0918(6) Uani 1 1 d . . .
S1 S 0.52107(4) 0.61083(3) 0.16034(4) 0.05826(15) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.381(3) . ?
C1 C2 1.397(3) . ?
C1 C9 1.458(3) . ?
C2 C3 1.363(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.396(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.504(3) . ?
C7 C8 1.539(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.538(3) . ?
C8 C10 1.550(3) . ?
C8 H8 0.9800 . ?
C9 O1 1.222(3) . ?
C10 N1 1.493(2) . ?
C10 C12 1.531(3) . ?
C10 C11 1.531(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C17 1.382(3) . ?
C12 C13 1.386(3) . ?
C13 C14 1.380(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.346(4) . ?
C14 H14 0.9300 . ?
C15 F1 1.369(3) . ?
C15 C16 1.374(4) . ?
C16 C17 1.384(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C20 1.513(3) . ?
C18 C19 1.517(3) . ?
C18 C21 1.531(3) . ?
C18 S1 1.844(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N1 S1 1.6585(16) . ?
N1 H1A 0.7842 . ?
O2 S1 1.4764(17) . ?

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 C2 122.1(2) . . ?
C6 C1 C9 109.94(19) . . ?
C2 C1 C9 128.0(2) . . ?
C3 C2 C1 118.4(3) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 122.3(3) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C4 C5 C6 118.2(3) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C5 119.4(2) . . ?
C1 C6 C7 111.80(19) . . ?
C5 C6 C7 128.8(2) . . ?
C6 C7 C8 105.01(16) . . ?
C6 C7 H7A 110.7 . . ?
C8 C7 H7A 110.7 . . ?
C6 C7 H7B 110.7 . . ?
C8 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
C9 C8 C7 104.79(16) . . ?
C9 C8 C10 112.81(15) . . ?
C7 C8 C10 115.45(17) . . ?
C9 C8 H8 107.8 . . ?
C7 C8 H8 107.8 . . ?
C10 C8 H8 107.8 . . ?
O1 C9 C1 126.4(2) . . ?
O1 C9 C8 125.40(19) . . ?
C1 C9 C8 108.15(17) . . ?
N1 C10 C12 107.46(14) . . ?
N1 C10 C11 111.42(17) . . ?
C12 C10 C11 113.40(17) . . ?
N1 C10 C8 104.31(14) . . ?
C12 C10 C8 109.98(15) . . ?
C11 C10 C8 109.85(17) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 118.0(2) . . ?
C17 C12 C10 119.90(17) . . ?
C13 C12 C10 122.00(18) . . ?
C14 C13 C12 121.0(2) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 118.6(2) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 F1 118.7(3) . . ?
C14 C15 C16 123.4(2) . . ?
F1 C15 C16 117.9(3) . . ?
C15 C16 C17 117.1(2) . . ?
C15 C16 H16 121.5 . . ?
C17 C16 H16 121.5 . . ?
C12 C17 C16 121.8(2) . . ?
C12 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C20 C18 C19 113.4(2) . . ?
C20 C18 C21 111.0(2) . . ?
C19 C18 C21 111.1(2) . . ?
C20 C18 S1 107.01(16) . . ?
C19 C18 S1 109.90(18) . . ?
C21 C18 S1 104.04(17) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C10 N1 S1 118.08(12) . . ?
C10 N1 H1A 108.7 . . ?
S1 N1 H1A 114.1 . . ?
O2 S1 N1 111.77(10) . . ?
O2 S1 C18 105.96(11) . . ?
N1 S1 C18 97.63(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
C6 C1 C2 C3 0.8(5) . . . . ?
C9 C1 C2 C3 179.9(3) . . . . ?
C1 C2 C3 C4 -0.7(6) . . . . ?
C2 C3 C4 C5 0.2(7) . . . . ?
C3 C4 C5 C6 0.3(7) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
C9 C1 C6 C5 -179.6(2) . . . . ?
C2 C1 C6 C7 178.5(2) . . . . ?
C9 C1 C6 C7 -0.7(3) . . . . ?
C4 C5 C6 C1 -0.2(5) . . . . ?
C4 C5 C6 C7 -178.8(3) . . . . ?
C1 C6 C7 C8 3.9(3) . . . . ?
C5 C6 C7 C8 -177.3(3) . . . . ?
C6 C7 C8 C9 -5.3(2) . . . . ?
C6 C7 C8 C10 -130.06(18) . . . . ?
C6 C1 C9 O1 176.3(2) . . . . ?
C2 C1 C9 O1 -2.8(4) . . . . ?
C6 C1 C9 C8 -2.9(3) . . . . ?
C2 C1 C9 C8 177.9(2) . . . . ?
C7 C8 C9 O1 -174.1(2) . . . . ?
C10 C8 C9 O1 -47.7(3) . . . . ?
C7 C8 C9 C1 5.2(2) . . . . ?
C10 C8 C9 C1 131.53(18) . . . . ?
C9 C8 C10 N1 68.43(19) . . . . ?
C7 C8 C10 N1 -171.12(16) . . . . ?
C9 C8 C10 C12 -176.59(16) . . . . ?
C7 C8 C10 C12 -56.1(2) . . . . ?
C9 C8 C10 C11 -51.1(2) . . . . ?
C7 C8 C10 C11 69.4(2) . . . . ?
N1 C10 C12 C17 55.6(2) . . . . ?
C11 C10 C12 C17 179.24(19) . . . . ?
C8 C10 C12 C17 -57.3(2) . . . . ?
N1 C10 C12 C13 -121.6(2) . . . . ?
C11 C10 C12 C13 2.0(3) . . . . ?
C8 C10 C12 C13 125.4(2) . . . . ?
C17 C12 C13 C14 -1.4(3) . . . . ?
C10 C12 C13 C14 175.9(2) . . . . ?
C12 C13 C14 C15 0.8(4) . . . . ?
C13 C14 C15 F1 179.7(2) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C14 C15 C16 C17 -0.3(4) . . . . ?
F1 C15 C16 C17 180.0(2) . . . . ?
C13 C12 C17 C16 1.1(3) . . . . ?
C10 C12 C17 C16 -176.25(19) . . . . ?
C15 C16 C17 C12 -0.3(3) . . . . ?
C12 C10 N1 S1 56.71(17) . . . . ?
C11 C10 N1 S1 -68.09(19) . . . . ?
C8 C10 N1 S1 173.45(12) . . . . ?
C10 N1 S1 O2 84.87(16) . . . . ?
C10 N1 S1 C18 -164.50(13) . . . . ?
C20 C18 S1 O2 -178.60(18) . . . . ?
C19 C18 S1 O2 57.93(18) . . . . ?
C21 C18 S1 O2 -61.06(17) . . . . ?
C20 C18 S1 N1 66.09(18) . . . . ?
C19 C18 S1 N1 -57.39(17) . . . . ?
C21 C18 S1 N1 -176.37(15) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.034
_database_code_depnum_ccdc_archive 'CCDC 951440'
