# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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.
# 
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#  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_2008src0405r

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 F N2 O3'
_chemical_formula_weight         367.39

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)/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                   27.4599(12)
_cell_length_b                   5.6654(2)
_cell_length_c                   11.4275(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.250(2)
_cell_angle_gamma                90.00
_cell_volume                     1776.42(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8342
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             772
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9427
_exptl_absorpt_correction_T_max  0.9970
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         none
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        negligible
_diffrn_reflns_number            17171
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_sigmaI/netI    0.0760
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3958
_reflns_number_gt                2535
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'DENZO, COLLECT'
_computing_data_reduction        'DENZO, COLLECT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_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.
;

_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)+(0.0641P)²+0.5579P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3958
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1448
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_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
H1N H -0.0925(10) 0.179(4) 0.559(2) 0.040(7) Uiso 1 1 d . . .
H2N H -0.0418(9) 0.046(4) 0.558(2) 0.034(7) Uiso 1 1 d . . .
C7 C 0.40084(7) 0.7536(3) 1.20975(18) 0.0206(5) Uani 1 1 d . . .
C8 C 0.40450(8) 0.5680(4) 1.29023(18) 0.0232(5) Uani 1 1 d . . .
H8 H 0.3841 0.4337 1.2800 0.028 Uiso 1 1 calc R . .
C9 C 0.43752(8) 0.5779(4) 1.38433(19) 0.0253(5) Uani 1 1 d . . .
H9 H 0.4392 0.4520 1.4393 0.030 Uiso 1 1 calc R . .
C10 C 0.46822(8) 0.7707(4) 1.39899(19) 0.0262(5) Uani 1 1 d . . .
H10 H 0.4910 0.7769 1.4638 0.031 Uiso 1 1 calc R . .
C11 C 0.46566(8) 0.9537(4) 1.31921(18) 0.0243(5) Uani 1 1 d . . .
H11 H 0.4871 1.0846 1.3283 0.029 Uiso 1 1 calc R . .
C12 C 0.43179(7) 0.9469(4) 1.22549(18) 0.0213(5) Uani 1 1 d . . .
H12 H 0.4297 1.0750 1.1719 0.026 Uiso 1 1 calc R . .
C13 C 0.36426(7) 0.7417(3) 1.11041(18) 0.0198(5) Uani 1 1 d . . .
C14 C 0.32960(7) 0.9169(4) 1.08788(18) 0.0216(5) Uani 1 1 d . . .
H14 H 0.3306 1.0544 1.1355 0.026 Uiso 1 1 calc R . .
F1 F 0.32840(9) 1.1098(4) 1.1619(2) 0.0303(6) Uani 0.50 1 d P A 1
C15 C 0.29387(7) 0.9010(4) 0.99990(19) 0.0231(5) Uani 1 1 d . . .
H15 H 0.2710 1.0253 0.9881 0.028 Uiso 1 1 calc R . .
C16 C 0.29150(7) 0.7014(4) 0.92836(18) 0.0206(5) Uani 1 1 d . . .
C17 C 0.32662(7) 0.5262(4) 0.94628(19) 0.0225(5) Uani 1 1 d . . .
H17 H 0.3265 0.3908 0.8973 0.027 Uiso 1 1 calc R . .
C18 C 0.36150(7) 0.5502(4) 1.03515(19) 0.0216(5) Uani 1 1 d . . .
H18 H 0.3850 0.4284 1.0455 0.026 Uiso 1 1 calc R . .
F1' F 0.39657(8) 0.3774(4) 1.0436(2) 0.0258(6) Uani 0.50 1 d P B 1
C19 C 0.25110(7) 0.6702(4) 0.83471(19) 0.0235(5) Uani 1 1 d . . .
H19 H 0.2611 0.5379 0.7829 0.028 Uiso 1 1 calc R . .
C20 C 0.24284(8) 0.8851(4) 0.7571(2) 0.0309(6) Uani 1 1 d . . .
H20A H 0.2292 1.0135 0.8031 0.046 Uiso 1 1 calc R . .
H20B H 0.2200 0.8449 0.6921 0.046 Uiso 1 1 calc R . .
H20C H 0.2739 0.9356 0.7261 0.046 Uiso 1 1 calc R . .
C21 C 0.20446(8) 0.5921(4) 0.89290(18) 0.0214(5) Uani 1 1 d . . .
O2 O 0.21176(5) 0.4019(3) 0.95834(14) 0.0291(4) Uani 1 1 d . . .
H2O H 0.1866 0.3734 0.9955 0.044 Uiso 1 1 calc R . .
O3 O 0.16547(5) 0.6918(3) 0.88062(14) 0.0301(4) Uani 1 1 d . . .
C1 C -0.07138(7) 0.4993(3) 0.40672(17) 0.0186(5) Uani 1 1 d . . .
C2 C -0.05382(8) 0.6236(4) 0.31246(18) 0.0210(5) Uani 1 1 d . . .
H2 H -0.0244 0.5763 0.2781 0.025 Uiso 1 1 calc R . .
C3 C -0.07955(8) 0.8169(4) 0.26902(19) 0.0240(5) Uani 1 1 d . . .
H3 H -0.0683 0.9028 0.2040 0.029 Uiso 1 1 calc R . .
C4 C -0.12172(8) 0.8822(4) 0.32189(19) 0.0243(5) Uani 1 1 d . . .
H4 H -0.1393 1.0151 0.2920 0.029 Uiso 1 1 calc R . .
C5 C -0.11426(7) 0.5778(4) 0.45388(18) 0.0205(5) Uani 1 1 d . . .
H5 H -0.1267 0.4932 0.5180 0.025 Uiso 1 1 calc R . .
C6 C -0.04241(7) 0.2931(4) 0.45273(18) 0.0193(5) Uani 1 1 d . . .
N1 N -0.13910(6) 0.7665(3) 0.41380(15) 0.0236(4) Uani 1 1 d . . .
N2 N -0.06059(7) 0.1603(3) 0.53735(16) 0.0229(4) Uani 1 1 d . . .
O1 O -0.00199(5) 0.2532(2) 0.41262(12) 0.0234(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
C7 C12 1.394(3) . ?
C7 C8 1.398(3) . ?
C7 C13 1.488(3) . ?
C8 C9 1.380(3) . ?
C9 C10 1.386(3) . ?
C10 C11 1.381(3) . ?
C11 C12 1.391(3) . ?
C13 C18 1.385(3) . ?
C13 C14 1.392(3) . ?
C14 C15 1.380(3) . ?
C15 C16 1.395(3) . ?
C16 C17 1.393(3) . ?
C16 C19 1.521(3) . ?
C17 C18 1.375(3) . ?
C19 C20 1.518(3) . ?
C19 C21 1.531(3) . ?
C21 O3 1.214(2) . ?
C21 O2 1.322(3) . ?
C1 C5 1.387(3) . ?
C1 C2 1.389(3) . ?
C1 C6 1.497(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.377(3) . ?
C4 N1 1.342(3) . ?
C5 N1 1.339(3) . ?
C6 O1 1.238(2) . ?
C6 N2 1.337(3) . ?

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
C12 C7 C8 118.6(2) . . ?
C12 C7 C13 121.62(18) . . ?
C8 C7 C13 119.79(18) . . ?
C9 C8 C7 120.7(2) . . ?
C8 C9 C10 120.3(2) . . ?
C11 C10 C9 119.8(2) . . ?
C10 C11 C12 120.2(2) . . ?
C11 C12 C7 120.46(19) . . ?
C18 C13 C14 115.04(19) . . ?
C18 C13 C7 121.89(18) . . ?
C14 C13 C7 123.04(18) . . ?
C15 C14 C13 123.3(2) . . ?
C14 C15 C16 119.70(19) . . ?
C17 C16 C15 118.36(19) . . ?
C17 C16 C19 120.13(19) . . ?
C15 C16 C19 121.50(19) . . ?
C18 C17 C16 119.8(2) . . ?
C17 C18 C13 123.75(19) . . ?
C20 C19 C16 113.93(18) . . ?
C20 C19 C21 112.16(18) . . ?
C16 C19 C21 109.11(17) . . ?
O3 C21 O2 123.92(19) . . ?
O3 C21 C19 124.4(2) . . ?
O2 C21 C19 111.73(18) . . ?
C5 C1 C2 117.70(19) . . ?
C5 C1 C6 124.13(18) . . ?
C2 C1 C6 118.16(17) . . ?
C3 C2 C1 119.41(19) . . ?
C4 C3 C2 118.8(2) . . ?
N1 C4 C3 122.9(2) . . ?
N1 C5 C1 123.48(19) . . ?
O1 C6 N2 122.03(19) . . ?
O1 C6 C1 118.96(18) . . ?
N2 C6 C1 119.00(18) . . ?
C5 N1 C4 117.77(18) . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.064


_database_code_depnum_ccdc_archive 'CCDC 981909'
