# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_140526a_0m
_database_code_depnum_ccdc_archive 'CCDC 1058835'
_audit_update_record             
;
2015-04-10 deposited with the CCDC.
2015-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H15 F2 N O'
_chemical_formula_sum            'C21 H15 F2 N O'
_chemical_formula_weight         335.34

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   5.498(5)
_cell_length_b                   9.083(8)
_cell_length_c                   16.538(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.524(10)
_cell_angle_gamma                90.00
_cell_volume                     825.1(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2109
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      27.10

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9730
_exptl_absorpt_correction_T_max  0.9922
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4258
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         25.04
_reflns_number_total             2878
_reflns_number_gt                2625
_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)+(0.0000P)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     SHELXL
_refine_ls_extinction_coef       0.049(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(6)
_refine_ls_number_reflns         2878
_refine_ls_number_parameters     228
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0549
_refine_ls_wR_factor_gt          0.0536
_refine_ls_goodness_of_fit_ref   1.603
_refine_ls_restrained_S_all      1.603
_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 0.6366(3) 0.70564(15) 0.74201(10) 0.0472(4) Uani 1 1 d . . .
C2 C 0.7939(3) 0.72790(16) 0.67838(12) 0.0591(5) Uani 1 1 d . . .
H2 H 0.7856 0.6655 0.6337 0.071 Uiso 1 1 calc R . .
C3 C 0.9599(4) 0.8410(2) 0.68163(13) 0.0713(6) Uani 1 1 d . . .
H3 H 1.0652 0.8544 0.6398 0.086 Uiso 1 1 calc R . .
C4 C 0.9694(4) 0.9349(2) 0.74763(15) 0.0749(6) Uani 1 1 d . . .
H4 H 1.0827 1.0110 0.7499 0.090 Uiso 1 1 calc R . .
C5 C 0.8153(3) 0.91797(19) 0.80954(13) 0.0667(5) Uani 1 1 d . . .
H5 H 0.8234 0.9835 0.8528 0.080 Uiso 1 1 calc R . .
C6 C 0.6431(3) 0.80146(16) 0.80859(10) 0.0497(4) Uani 1 1 d . . .
C7 C 0.4752(3) 0.77533(18) 0.87202(10) 0.0525(4) Uani 1 1 d . . .
C8 C 0.4599(4) 0.8677(2) 0.94053(13) 0.0760(6) Uani 1 1 d . . .
H8 H 0.5611 0.9495 0.9457 0.091 Uiso 1 1 calc R . .
C9 C 0.2994(4) 0.8388(3) 0.99895(13) 0.0853(7) Uani 1 1 d . . .
H9 H 0.2927 0.9011 1.0434 0.102 Uiso 1 1 calc R . .
C10 C 0.1451(4) 0.7174(2) 0.99311(12) 0.0741(6) Uani 1 1 d . . .
H10 H 0.0352 0.6992 1.0331 0.089 Uiso 1 1 calc R . .
C11 C 0.1567(3) 0.6255(2) 0.92827(11) 0.0635(5) Uani 1 1 d . . .
H11 H 0.0536 0.5444 0.9244 0.076 Uiso 1 1 calc R . .
C12 C 0.3227(3) 0.65086(18) 0.86656(10) 0.0479(4) Uani 1 1 d . . .
C13 C 0.3432(3) 0.55658(16) 0.79613(10) 0.0432(4) Uani 1 1 d . . .
C14 C 0.2026(3) 0.41148(17) 0.78856(10) 0.0481(4) Uani 1 1 d . . .
C15 C 0.2327(3) 0.32058(17) 0.71425(9) 0.0428(4) Uani 1 1 d . . .
C16 C 0.0605(3) 0.32591(18) 0.65037(10) 0.0524(4) Uani 1 1 d . . .
H16 H -0.0723 0.3888 0.6532 0.063 Uiso 1 1 calc R . .
C17 C 0.0838(3) 0.23874(17) 0.58248(11) 0.0559(5) Uani 1 1 d . . .
H17 H -0.0321 0.2438 0.5399 0.067 Uiso 1 1 calc R . .
C18 C 0.2807(3) 0.14369(17) 0.57802(10) 0.0486(4) Uani 1 1 d . . .
C19 C 0.4549(3) 0.13796(18) 0.64115(10) 0.0509(4) Uani 1 1 d . . .
H19 H 0.5878 0.0751 0.6384 0.061 Uiso 1 1 calc R . .
C20 C 0.4292(3) 0.22660(16) 0.70817(11) 0.0494(4) Uani 1 1 d . . .
H20 H 0.5469 0.2230 0.7503 0.059 Uiso 1 1 calc R . .
C21 C 0.4969(4) -0.0267(2) 0.49589(14) 0.0865(7) Uani 1 1 d . . .
H21A H 0.5123 -0.1012 0.5370 0.130 Uiso 1 1 calc R . .
H21B H 0.6386 0.0352 0.4987 0.130 Uiso 1 1 calc R . .
H21C H 0.4822 -0.0725 0.4436 0.130 Uiso 1 1 calc R . .
F1 F 0.27153(18) 0.32820(10) 0.85629(6) 0.0662(3) Uani 1 1 d . . .
F2 F -0.04192(17) 0.43829(11) 0.79766(6) 0.0675(3) Uani 1 1 d . . .
N1 N 0.4846(2) 0.58260(13) 0.73677(8) 0.0461(3) Uani 1 1 d . . .
O1 O 0.2846(2) 0.06057(13) 0.50849(7) 0.0682(4) 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 N1 1.396(2) . ?
C1 C2 1.406(2) . ?
C1 C6 1.403(2) . ?
C2 C3 1.374(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.420(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.447(2) . ?
C7 C12 1.408(2) . ?
C7 C8 1.416(2) . ?
C8 C9 1.363(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.392(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.363(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.418(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.454(2) . ?
C13 N1 1.300(2) . ?
C13 C14 1.530(2) . ?
C14 F2 1.381(2) . ?
C14 F1 1.3903(19) . ?
C14 C15 1.496(2) . ?
C15 C20 1.384(2) . ?
C15 C16 1.388(2) . ?
C16 C17 1.384(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.389(2) . ?
C17 H17 0.9300 . ?
C18 O1 1.377(2) . ?
C18 C19 1.387(2) . ?
C19 C20 1.382(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 O1 1.434(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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
N1 C1 C2 117.07(15) . . ?
N1 C1 C6 122.68(15) . . ?
C2 C1 C6 120.20(16) . . ?
C3 C2 C1 120.52(19) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.58(19) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 121.23(19) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 120.73(19) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 117.72(17) . . ?
C1 C6 C7 118.18(15) . . ?
C5 C6 C7 124.11(16) . . ?
C12 C7 C8 118.12(18) . . ?
C12 C7 C6 118.83(15) . . ?
C8 C7 C6 123.04(17) . . ?
C9 C8 C7 121.1(2) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 121.0(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 121.4(2) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C7 C12 C11 119.00(16) . . ?
C7 C12 C13 117.21(15) . . ?
C11 C12 C13 123.77(16) . . ?
N1 C13 C12 124.59(15) . . ?
N1 C13 C14 114.29(14) . . ?
C12 C13 C14 121.06(14) . . ?
F2 C14 F1 103.90(12) . . ?
F2 C14 C15 109.30(13) . . ?
F1 C14 C15 108.99(14) . . ?
F2 C14 C13 109.26(13) . . ?
F1 C14 C13 106.50(13) . . ?
C15 C14 C13 117.95(13) . . ?
C20 C15 C16 118.33(16) . . ?
C20 C15 C14 121.02(15) . . ?
C16 C15 C14 120.63(15) . . ?
C17 C16 C15 120.84(16) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 119.93(16) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
O1 C18 C19 124.94(16) . . ?
O1 C18 C17 115.22(15) . . ?
C19 C18 C17 119.84(16) . . ?
C20 C19 C18 119.35(16) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C15 121.70(16) . . ?
C19 C20 H20 119.2 . . ?
C15 C20 H20 119.2 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C13 N1 C1 118.34(14) . . ?
C18 O1 C21 117.85(14) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.106
_refine_diff_density_min         -0.092
_refine_diff_density_rms         0.022
