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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_0901-whs-wyc-1
_audit_creation_date             2013-09-03
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H14 N2'
_chemical_formula_sum            'C16 H14 N2'
_chemical_formula_weight         234.29
_chemical_melting_point          ?
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   9.9757(3)
_cell_length_b                   5.76438(17)
_cell_length_c                   22.7227(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.835(3)
_cell_angle_gamma                90.00
_cell_volume                     1305.97(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3192
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7614
_cell_measurement_theta_min      3.3197
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9336
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.59
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9784
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -23.00    2.00   1.0000   12.3800
omega____ theta____ kappa____ phi______ frames
    -      -16.8791  -57.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -85.00    9.00   1.0000   12.3800
omega____ theta____ kappa____ phi______ frames
    -      -16.8791  -77.0000  120.0000 94

#__ type_ start__ end____ width___ exp.time_
  3 omega  -76.00  -46.00   1.0000   12.3800
omega____ theta____ kappa____ phi______ frames
    -      -16.8791  133.0000  -49.0000 30

#__ type_ start__ end____ width___ exp.time_
  4 omega  -46.00   47.00   1.0000   12.3800
omega____ theta____ kappa____ phi______ frames
    -      -16.8791   77.0000 -120.0000 93

#__ type_ start__ end____ width___ exp.time_
  5 omega  -52.00   54.00   1.0000   12.3800
omega____ theta____ kappa____ phi______ frames
    -      -16.8791   19.0000   60.0000 106

#__ type_ start__ end____ width___ exp.time_
  6 omega  -91.00  -66.00   1.0000   12.3800
omega____ theta____ kappa____ phi______ frames
    -      -16.8791 -178.0000   30.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0708139000
_diffrn_orient_matrix_UB_12      -0.0067344000
_diffrn_orient_matrix_UB_13      0.0034452000
_diffrn_orient_matrix_UB_21      -0.0055229000
_diffrn_orient_matrix_UB_22      0.0024691000
_diffrn_orient_matrix_UB_23      0.0310326000
_diffrn_orient_matrix_UB_31      -0.0040032000
_diffrn_orient_matrix_UB_32      -0.1228487000
_diffrn_orient_matrix_UB_33      0.0004333000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2075
_reflns_number_total             2662
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.112
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2662
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0484
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0316P)²+0.4136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1209
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
N1 N 0.10620(14) 1.1043(3) 0.44928(6) 0.0553(4) Uani 1 1 d . . .
H1 H 0.0916 1.2210 0.4717 0.066 Uiso 1 1 calc R . .
N2 N -0.09983(18) 1.5924(3) 0.44204(8) 0.0724(5) Uani 1 1 d . . .
C1 C 0.37452(19) 1.1226(3) 0.40525(8) 0.0587(5) Uani 1 1 d . . .
H1A H 0.3168 1.2473 0.3988 0.070 Uiso 1 1 calc R . .
C2 C 0.4982(2) 1.1217(4) 0.37972(10) 0.0750(6) Uani 1 1 d . . .
H2 H 0.5232 1.2453 0.3562 0.090 Uiso 1 1 calc R . .
C3 C 0.5838(2) 0.9394(5) 0.38895(11) 0.0800(7) Uani 1 1 d . . .
H3 H 0.6670 0.9387 0.3716 0.096 Uiso 1 1 calc R . .
C4 C 0.5472(2) 0.7589(4) 0.42349(10) 0.0780(6) Uani 1 1 d . . .
H4 H 0.6057 0.6352 0.4300 0.094 Uiso 1 1 calc R . .
C5 C 0.42410(18) 0.7587(3) 0.44880(8) 0.0601(5) Uani 1 1 d . . .
H5 H 0.3998 0.6340 0.4722 0.072 Uiso 1 1 calc R . .
C6 C 0.33559(16) 0.9411(3) 0.44012(7) 0.0464(4) Uani 1 1 d . . .
C7 C 0.20225(17) 0.9311(3) 0.46926(8) 0.0576(5) Uani 1 1 d . . .
H7A H 0.1635 0.7787 0.4625 0.069 Uiso 1 1 calc R . .
H7B H 0.2174 0.9487 0.5114 0.069 Uiso 1 1 calc R . .
C8 C 0.03937(16) 1.0913(3) 0.39766(7) 0.0489(4) Uani 1 1 d . . .
H8 H 0.0580 0.9639 0.3742 0.059 Uiso 1 1 calc R . .
C9 C -0.05305(16) 1.2440(3) 0.37561(7) 0.0456(4) Uani 1 1 d . . .
C10 C -0.08090(17) 1.4389(3) 0.41140(8) 0.0512(4) Uani 1 1 d . . .
C11 C -0.12697(16) 1.2218(3) 0.31859(7) 0.0472(4) Uani 1 1 d . . .
C12 C -0.1099(2) 1.0334(4) 0.28158(8) 0.0630(5) Uani 1 1 d . . .
H12 H -0.0487 0.9179 0.2922 0.076 Uiso 1 1 calc R . .
C13 C -0.1828(2) 1.0157(4) 0.22914(9) 0.0766(6) Uani 1 1 d . . .
H13 H -0.1702 0.8880 0.2049 0.092 Uiso 1 1 calc R . .
C14 C -0.2733(2) 1.1829(5) 0.21221(9) 0.0791(6) Uani 1 1 d . . .
H14 H -0.3223 1.1691 0.1769 0.095 Uiso 1 1 calc R . .
C15 C -0.2906(2) 1.3707(4) 0.24792(10) 0.0791(6) Uani 1 1 d . . .
H15 H -0.3516 1.4857 0.2368 0.095 Uiso 1 1 calc R . .
C16 C -0.2177(2) 1.3904(3) 0.30049(8) 0.0626(5) Uani 1 1 d . . .
H16 H -0.2301 1.5198 0.3241 0.075 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0520(8) 0.0682(10) 0.0456(8) -0.0056(7) -0.0012(6) 0.0125(7)
N2 0.0822(12) 0.0679(11) 0.0659(11) -0.0158(9) -0.0151(9) 0.0176(9)
C1 0.0602(11) 0.0566(11) 0.0592(11) 0.0040(9) 0.0011(9) -0.0014(9)
C2 0.0720(14) 0.0799(15) 0.0737(14) 0.0049(11) 0.0125(11) -0.0195(12)
C3 0.0530(12) 0.1049(19) 0.0830(16) -0.0134(14) 0.0155(11) -0.0076(13)
C4 0.0568(12) 0.0862(16) 0.0910(16) -0.0042(13) 0.0021(11) 0.0163(12)
C5 0.0587(11) 0.0625(12) 0.0588(11) 0.0048(9) -0.0036(9) 0.0072(9)
C6 0.0479(9) 0.0522(10) 0.0385(8) -0.0024(7) -0.0063(7) -0.0006(8)
C7 0.0508(10) 0.0697(12) 0.0522(10) 0.0109(9) -0.0010(8) 0.0057(9)
C8 0.0488(9) 0.0554(10) 0.0430(9) -0.0016(8) 0.0074(7) 0.0035(8)
C9 0.0452(9) 0.0492(9) 0.0427(9) 0.0007(7) 0.0054(7) 0.0005(8)
C10 0.0479(9) 0.0569(11) 0.0486(10) 0.0015(8) -0.0042(7) 0.0039(8)
C11 0.0465(9) 0.0542(10) 0.0413(9) 0.0032(7) 0.0057(7) -0.0026(8)
C12 0.0666(12) 0.0685(12) 0.0538(11) -0.0085(9) -0.0013(9) 0.0102(10)
C13 0.0889(16) 0.0883(16) 0.0522(12) -0.0171(11) -0.0037(11) 0.0024(13)
C14 0.0872(16) 0.1003(17) 0.0486(12) 0.0015(12) -0.0152(10) -0.0033(14)
C15 0.0867(15) 0.0843(16) 0.0650(14) 0.0098(12) -0.0190(12) 0.0132(13)
C16 0.0726(12) 0.0608(12) 0.0540(11) 0.0019(9) -0.0051(9) 0.0106(10)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 H1 0.8600 . ?
N1 C7 1.447(2) . ?
N1 C8 1.333(2) . ?
N2 C10 1.145(2) . ?
C1 H1A 0.9300 . ?
C1 C2 1.380(3) . ?
C1 C6 1.376(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.366(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.361(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(2) . ?
C6 C7 1.506(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8 0.9300 . ?
C8 C9 1.359(2) . ?
C9 C10 1.419(2) . ?
C9 C11 1.476(2) . ?
C11 C12 1.388(2) . ?
C11 C16 1.381(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.367(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.367(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.383(3) . ?
C16 H16 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
C7 N1 H1 118.5 . . ?
C8 N1 H1 118.5 . . ?
C8 N1 C7 123.03(15) . . ?
C2 C1 H1A 119.6 . . ?
C6 C1 H1A 119.6 . . ?
C6 C1 C2 120.80(19) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.01(19) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.00(17) . . ?
C1 C6 C7 123.52(16) . . ?
C5 C6 C7 118.48(16) . . ?
N1 C7 C6 114.88(15) . . ?
N1 C7 H7A 108.5 . . ?
N1 C7 H7B 108.5 . . ?
C6 C7 H7A 108.5 . . ?
C6 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
N1 C8 H8 116.5 . . ?
N1 C8 C9 127.04(16) . . ?
C9 C8 H8 116.5 . . ?
C8 C9 C10 116.39(15) . . ?
C8 C9 C11 125.56(15) . . ?
C10 C9 C11 118.04(15) . . ?
N2 C10 C9 177.15(19) . . ?
C12 C11 C9 122.17(16) . . ?
C16 C11 C9 120.31(16) . . ?
C16 C11 C12 117.52(17) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.65(19) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.0(2) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.1(2) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.3(2) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 121.38(19) . . ?
C11 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?

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
N1 C8 C9 C10 0.3(3) . . . . ?
N1 C8 C9 C11 -178.86(16) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C1 C6 C7 N1 11.3(3) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C1 C6 C7 -179.98(18) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C4 C5 C6 C7 -179.79(18) . . . . ?
C5 C6 C7 N1 -168.76(16) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
C7 N1 C8 C9 179.39(16) . . . . ?
C8 N1 C7 C6 75.5(2) . . . . ?
C8 C9 C10 N2 -4(4) . . . . ?
C8 C9 C11 C12 1.4(3) . . . . ?
C8 C9 C11 C16 -179.22(17) . . . . ?
C9 C11 C12 C13 178.59(18) . . . . ?
C9 C11 C16 C15 -178.41(18) . . . . ?
C10 C9 C11 C12 -177.73(17) . . . . ?
C10 C9 C11 C16 1.7(2) . . . . ?
C11 C9 C10 N2 176(100) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C11 C16 C15 1.0(3) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
C14 C15 C16 C11 -0.5(3) . . . . ?
C16 C11 C12 C13 -0.8(3) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1005487'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_aa
_audit_creation_date             2014-01-06
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H13 F N2'
_chemical_formula_sum            'C16 H13 F N2'
_chemical_formula_weight         252.28
_chemical_melting_point          ?
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.8434(17)
_cell_length_b                   10.203(3)
_cell_length_c                   22.194(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.840(5)
_cell_angle_gamma                90.00
_cell_volume                     1318.5(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_correction_T_min  0.9747
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14607
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.84
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2146
_reflns_number_total             2699
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2699
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0508P)²+0.2424P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1112
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.46116(16) 0.68410(11) 0.66091(4) 0.0732(3) Uani 1 1 d . . .
N1 N 0.5869(2) 1.11566(11) 0.95256(5) 0.0464(3) Uani 1 1 d . . .
H1 H 0.7126 1.1003 0.9745 0.056 Uiso 1 1 calc R . .
C4 C 0.6242(2) 0.89017(12) 0.81904(5) 0.0360(3) Uani 1 1 d . . .
C11 C 0.4240(2) 1.34132(13) 0.94079(6) 0.0409(3) Uani 1 1 d . . .
C7 C 0.6813(2) 0.95929(12) 0.87689(5) 0.0370(3) Uani 1 1 d . . .
C8 C 0.8934(2) 0.92848(13) 0.91027(6) 0.0423(3) Uani 1 1 d . . .
C9 C 0.5451(2) 1.05085(12) 0.90071(6) 0.0389(3) Uani 1 1 d . . .
H9 H 0.4076 1.0702 0.8783 0.047 Uiso 1 1 calc R . .
N2 N 1.0612(2) 0.90525(14) 0.93875(6) 0.0603(4) Uani 1 1 d . . .
C2 C 0.3629(3) 0.84171(16) 0.73126(7) 0.0547(4) Uani 1 1 d . . .
H2 H 0.2244 0.8563 0.7084 0.066 Uiso 1 1 calc R . .
C3 C 0.4162(2) 0.90982(15) 0.78442(7) 0.0501(4) Uani 1 1 d . . .
H3 H 0.3114 0.9700 0.7974 0.060 Uiso 1 1 calc R . .
C6 C 0.7226(3) 0.73065(16) 0.74470(7) 0.0558(4) Uani 1 1 d . . .
H6 H 0.8254 0.6700 0.7312 0.067 Uiso 1 1 calc R . .
C5 C 0.7755(2) 0.80024(15) 0.79757(6) 0.0480(3) Uani 1 1 d . . .
H5 H 0.9166 0.7863 0.8193 0.058 Uiso 1 1 calc R . .
C16 C 0.5958(3) 1.38014(15) 0.90558(7) 0.0526(4) Uani 1 1 d . . .
H16 H 0.7192 1.3245 0.9009 0.063 Uiso 1 1 calc R . .
C12 C 0.2427(3) 1.42611(15) 0.94691(7) 0.0567(4) Uani 1 1 d . . .
H12 H 0.1249 1.4016 0.9703 0.068 Uiso 1 1 calc R . .
C10 C 0.4275(3) 1.21118(14) 0.97324(6) 0.0475(3) Uani 1 1 d . . .
H10A H 0.4658 1.2266 1.0160 0.057 Uiso 1 1 calc R . .
H10B H 0.2741 1.1741 0.9686 0.057 Uiso 1 1 calc R . .
C1 C 0.5161(3) 0.75301(15) 0.71283(6) 0.0497(4) Uani 1 1 d . . .
C13 C 0.2351(3) 1.54672(17) 0.91866(9) 0.0717(5) Uani 1 1 d . . .
H13 H 0.1128 1.6031 0.9234 0.086 Uiso 1 1 calc R . .
C15 C 0.5862(3) 1.50074(17) 0.87730(8) 0.0676(5) Uani 1 1 d . . .
H15 H 0.7027 1.5259 0.8537 0.081 Uiso 1 1 calc R . .
C14 C 0.4048(4) 1.58374(17) 0.88402(9) 0.0730(5) Uani 1 1 d . . .
H14 H 0.3982 1.6649 0.8649 0.088 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0688(6) 0.0870(7) 0.0616(6) -0.0316(5) -0.0073(5) -0.0042(5)
N1 0.0513(7) 0.0460(6) 0.0401(6) 0.0001(5) -0.0061(5) 0.0081(5)
C4 0.0346(6) 0.0350(6) 0.0380(7) 0.0052(5) 0.0005(5) -0.0037(5)
C11 0.0431(7) 0.0419(7) 0.0368(7) -0.0051(5) -0.0014(5) -0.0016(6)
C7 0.0351(6) 0.0373(6) 0.0378(6) 0.0054(5) -0.0020(5) -0.0006(5)
C8 0.0415(7) 0.0449(7) 0.0398(7) -0.0008(6) -0.0001(6) 0.0006(6)
C9 0.0392(7) 0.0405(7) 0.0360(6) 0.0065(5) -0.0033(5) 0.0013(5)
N2 0.0483(7) 0.0761(9) 0.0536(7) -0.0065(6) -0.0125(6) 0.0117(6)
C2 0.0447(8) 0.0628(9) 0.0536(8) -0.0074(7) -0.0136(6) 0.0023(7)
C3 0.0431(7) 0.0521(8) 0.0533(8) -0.0080(6) -0.0072(6) 0.0097(6)
C6 0.0475(8) 0.0626(9) 0.0573(9) -0.0159(7) 0.0048(7) 0.0072(7)
C5 0.0379(7) 0.0562(8) 0.0489(8) -0.0034(6) -0.0023(6) 0.0058(6)
C16 0.0475(8) 0.0546(8) 0.0557(9) 0.0034(7) 0.0043(7) -0.0007(7)
C12 0.0533(9) 0.0526(9) 0.0648(10) -0.0036(7) 0.0091(7) 0.0048(7)
C10 0.0568(8) 0.0472(8) 0.0392(7) -0.0003(6) 0.0081(6) 0.0030(6)
C1 0.0502(8) 0.0538(8) 0.0445(7) -0.0103(6) -0.0001(6) -0.0091(7)
C13 0.0714(12) 0.0498(9) 0.0925(13) -0.0012(9) -0.0014(10) 0.0146(8)
C15 0.0671(11) 0.0629(10) 0.0723(11) 0.0156(9) 0.0036(9) -0.0171(9)
C14 0.0871(13) 0.0448(9) 0.0839(13) 0.0139(8) -0.0119(11) -0.0081(9)

_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 C1 1.3650(16) . ?
N1 H1 0.8600 . ?
N1 C9 1.3320(17) . ?
N1 C10 1.4495(18) . ?
C4 C7 1.4782(17) . ?
C4 C3 1.3962(18) . ?
C4 C5 1.3864(19) . ?
C11 C16 1.381(2) . ?
C11 C12 1.384(2) . ?
C11 C10 1.5099(19) . ?
C7 C8 1.4244(17) . ?
C7 C9 1.3627(18) . ?
C8 N2 1.1457(17) . ?
C9 H9 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.382(2) . ?
C2 C1 1.360(2) . ?
C3 H3 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.384(2) . ?
C6 C1 1.365(2) . ?
C5 H5 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.380(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C13 H13 0.9300 . ?
C13 C14 1.359(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.375(3) . ?
C14 H14 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
C9 N1 H1 119.0 . . ?
C9 N1 C10 122.09(12) . . ?
C10 N1 H1 119.0 . . ?
C3 C4 C7 122.12(12) . . ?
C5 C4 C7 120.69(11) . . ?
C5 C4 C3 117.18(12) . . ?
C16 C11 C12 118.39(14) . . ?
C16 C11 C10 122.75(12) . . ?
C12 C11 C10 118.85(13) . . ?
C8 C7 C4 117.99(11) . . ?
C9 C7 C4 124.57(11) . . ?
C9 C7 C8 117.43(12) . . ?
N2 C8 C7 177.82(15) . . ?
N1 C9 C7 127.21(12) . . ?
N1 C9 H9 116.4 . . ?
C7 C9 H9 116.4 . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.00(13) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 C4 121.36(13) . . ?
C2 C3 H3 119.3 . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
C1 C6 C5 118.56(14) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.83(13) . . ?
C6 C5 H5 119.1 . . ?
C11 C16 H16 119.7 . . ?
C15 C16 C11 120.61(15) . . ?
C15 C16 H16 119.7 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.57(16) . . ?
C13 C12 H12 119.7 . . ?
N1 C10 C11 115.04(11) . . ?
N1 C10 H10A 108.5 . . ?
N1 C10 H10B 108.5 . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
F1 C1 C6 119.08(13) . . ?
C2 C1 F1 118.86(13) . . ?
C2 C1 C6 122.06(13) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.53(17) . . ?
C14 C13 H13 119.7 . . ?
C16 C15 H15 119.9 . . ?
C14 C15 C16 120.15(17) . . ?
C14 C15 H15 119.9 . . ?
C13 C14 C15 119.76(16) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?

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
C4 C7 C8 N2 -159(4) . . . . ?
C4 C7 C9 N1 179.66(12) . . . . ?
C11 C16 C15 C14 0.1(3) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C7 C4 C3 C2 -178.21(14) . . . . ?
C7 C4 C5 C6 177.56(13) . . . . ?
C8 C7 C9 N1 -0.4(2) . . . . ?
C9 N1 C10 C11 -75.32(17) . . . . ?
C9 C7 C8 N2 21(4) . . . . ?
C3 C4 C7 C8 177.30(13) . . . . ?
C3 C4 C7 C9 -2.7(2) . . . . ?
C3 C4 C5 C6 -1.2(2) . . . . ?
C3 C2 C1 F1 178.77(14) . . . . ?
C3 C2 C1 C6 -1.1(3) . . . . ?
C5 C4 C7 C8 -1.35(18) . . . . ?
C5 C4 C7 C9 178.63(13) . . . . ?
C5 C4 C3 C2 0.5(2) . . . . ?
C5 C6 C1 F1 -179.42(14) . . . . ?
C5 C6 C1 C2 0.4(3) . . . . ?
C16 C11 C12 C13 -0.3(2) . . . . ?
C16 C11 C10 N1 -15.93(19) . . . . ?
C16 C15 C14 C13 0.1(3) . . . . ?
C12 C11 C16 C15 0.0(2) . . . . ?
C12 C11 C10 N1 164.71(13) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C10 N1 C9 C7 -179.88(13) . . . . ?
C10 C11 C16 C15 -179.32(14) . . . . ?
C10 C11 C12 C13 179.07(15) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
C1 C6 C5 C4 0.7(2) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1005488'
