# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1470379'
_audit_update_record             
;
2016-03-24 deposited with the CCDC.
2016-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H13 N O2'
_chemical_formula_sum            'C11 H13 N O2'
_chemical_formula_weight         191.22

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   8.9638(18)
_cell_length_b                   10.520(2)
_cell_length_c                   11.467(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.75(3)
_cell_angle_gamma                90.00
_cell_volume                     1017.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7746
_cell_measurement_theta_min      3.095
_cell_measurement_theta_max      27.575

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.547
_exptl_crystal_size_mid          0.412
_exptl_crystal_size_min          0.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9802
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2324
_reflns_number_gt                1792
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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. 
;

_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)+(0.1029P)²+0.0301P] 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         2324
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1583
_refine_ls_wR_factor_gt          0.1490
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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 0.19813(13) 0.23046(11) 0.32842(10) 0.0403(3) Uani 1 1 d . . .
O2 O 0.09595(12) 0.23793(12) 0.49334(9) 0.0658(3) Uani 1 1 d . . .
O3 O 0.33126(14) 0.36587(12) 0.50091(9) 0.0669(4) Uani 1 1 d . . .
H3 H 0.2602 0.3373 0.5233 0.100 Uiso 1 1 calc R . .
C4 C 0.07636(14) 0.19686(12) 0.38534(11) 0.0433(3) Uani 1 1 d . . .
C5 C 0.32243(14) 0.31326(12) 0.39164(11) 0.0453(3) Uani 1 1 d . . .
C6 C -0.05791(14) 0.12302(12) 0.31910(11) 0.0443(3) Uani 1 1 d . . .
H6 H -0.0732 0.0978 0.2381 0.053 Uiso 1 1 calc R . .
C7 C 0.19664(15) 0.18188(13) 0.21427(11) 0.0479(3) Uani 1 1 d . . .
H7 H 0.1155 0.1273 0.1704 0.058 Uiso 1 1 calc R . .
N N -0.29814(13) 0.02488(11) 0.32672(11) 0.0538(3) Uani 1 1 d . . .
C9 C 0.44011(16) 0.34332(14) 0.34183(13) 0.0544(4) Uani 1 1 d . . .
H9 H 0.5226 0.3973 0.3847 0.065 Uiso 1 1 calc R . .
C10 C -0.16501(15) 0.08901(13) 0.37501(12) 0.0484(3) Uani 1 1 d . . .
H10 H -0.1409 0.1142 0.4571 0.058 Uiso 1 1 calc R . .
C11 C 0.43455(17) 0.29349(15) 0.22984(14) 0.0573(4) Uani 1 1 d . . .
H11 H 0.5133 0.3140 0.1971 0.069 Uiso 1 1 calc R . .
C12 C -0.35200(19) -0.01779(17) 0.19937(16) 0.0705(5) Uani 1 1 d . . .
H12A H -0.3336 0.0478 0.1476 0.106 Uiso 1 1 calc R . .
H12B H -0.4633 -0.0365 0.1735 0.106 Uiso 1 1 calc R . .
H12C H -0.2949 -0.0930 0.1925 0.106 Uiso 1 1 calc R . .
C13 C 0.31297(17) 0.21327(15) 0.16565(13) 0.0571(4) Uani 1 1 d . . .
H13 H 0.3094 0.1803 0.0895 0.068 Uiso 1 1 calc R . .
C14 C -0.3979(2) -0.00581(18) 0.40088(18) 0.0759(5) Uani 1 1 d . . .
H14A H -0.3495 0.0265 0.4834 0.114 Uiso 1 1 calc R . .
H14B H -0.4093 -0.0964 0.4039 0.114 Uiso 1 1 calc R . .
H14C H -0.5004 0.0324 0.3640 0.114 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
C1 0.0380(6) 0.0443(6) 0.0388(6) 0.0042(5) 0.0133(5) 0.0019(4)
O2 0.0599(6) 0.0970(8) 0.0473(6) -0.0179(5) 0.0271(5) -0.0183(5)
O3 0.0640(7) 0.0860(8) 0.0523(6) -0.0223(5) 0.0219(5) -0.0231(5)
C4 0.0426(6) 0.0494(7) 0.0403(6) 0.0014(5) 0.0171(5) 0.0024(5)
C5 0.0449(6) 0.0476(7) 0.0411(6) 0.0016(5) 0.0114(5) -0.0014(5)
C6 0.0439(6) 0.0488(7) 0.0439(6) -0.0007(5) 0.0196(5) -0.0009(5)
C7 0.0458(7) 0.0562(8) 0.0441(7) -0.0056(5) 0.0183(6) -0.0074(5)
N 0.0473(6) 0.0572(7) 0.0642(7) 0.0092(5) 0.0284(6) -0.0040(5)
C9 0.0476(7) 0.0559(8) 0.0589(8) 0.0042(6) 0.0171(6) -0.0111(6)
C10 0.0469(7) 0.0528(7) 0.0493(7) 0.0061(5) 0.0211(6) 0.0026(5)
C11 0.0523(7) 0.0670(9) 0.0600(8) 0.0080(6) 0.0285(7) -0.0062(6)
C12 0.0578(9) 0.0767(11) 0.0811(11) -0.0150(8) 0.0287(8) -0.0211(7)
C13 0.0582(8) 0.0721(9) 0.0486(7) -0.0043(6) 0.0281(7) -0.0064(7)
C14 0.0585(9) 0.0941(13) 0.0887(12) 0.0279(10) 0.0426(9) -0.0021(8)

_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 C7 1.4009(16) . ?
C1 C5 1.4070(17) . ?
C1 C4 1.4913(16) . ?
O2 C4 1.2666(15) . ?
O3 C5 1.3473(15) . ?
C4 C6 1.4181(18) . ?
C5 C9 1.3951(18) . ?
C6 C10 1.3699(17) . ?
C7 C13 1.3785(18) . ?
N C10 1.3188(18) . ?
N C12 1.446(2) . ?
N C14 1.4634(17) . ?
C9 C11 1.372(2) . ?
C11 C13 1.378(2) . ?

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 C1 C5 117.59(11) . . ?
C7 C1 C4 123.03(11) . . ?
C5 C1 C4 119.37(11) . . ?
O2 C4 C6 121.51(11) . . ?
O2 C4 C1 117.84(11) . . ?
C6 C4 C1 120.64(11) . . ?
O3 C5 C9 118.21(12) . . ?
O3 C5 C1 121.39(11) . . ?
C9 C5 C1 120.40(12) . . ?
C10 C6 C4 119.64(11) . . ?
C13 C7 C1 121.39(12) . . ?
C10 N C12 121.92(11) . . ?
C10 N C14 120.86(14) . . ?
C12 N C14 117.22(13) . . ?
C11 C9 C5 120.21(13) . . ?
N C10 C6 127.95(13) . . ?
C9 C11 C13 120.39(12) . . ?
C11 C13 C7 120.02(12) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.062
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1470380'
_audit_update_record             
;
2016-03-24 deposited with the CCDC.
2016-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H12 F N O2'
_chemical_formula_sum            'C11 H12 F N O2'
_chemical_formula_weight         209.22

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
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   7.7034(15)
_cell_length_b                   22.119(4)
_cell_length_c                   12.573(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.27(3)
_cell_angle_gamma                90.00
_cell_volume                     2066.7(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    13856
_cell_measurement_theta_min      3.235
_cell_measurement_theta_max      27.46

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.506
_exptl_crystal_size_mid          0.442
_exptl_crystal_size_min          0.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20171
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4717
_reflns_number_gt                3026
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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. 
;

_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)+(0.0857P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4717
_refine_ls_number_parameters     277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1391
_refine_ls_wR_factor_gt          0.1271
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_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
C30 C 0.0646(3) 0.18463(7) 0.06792(12) 0.0695(4) Uani 1 1 d . . .
H30A H 0.1770 0.1723 0.0553 0.104 Uiso 1 1 calc R . .
H30B H -0.0326 0.1717 0.0074 0.104 Uiso 1 1 calc R . .
H30C H 0.0519 0.1667 0.1350 0.104 Uiso 1 1 calc R . .
C26 C -0.0406(2) 0.28291(8) -0.01828(12) 0.0677(4) Uani 1 1 d . . .
H26A H -0.0311 0.3255 -0.0028 0.102 Uiso 1 1 calc R . .
H26B H -0.1647 0.2710 -0.0352 0.102 Uiso 1 1 calc R . .
H26C H 0.0066 0.2743 -0.0801 0.102 Uiso 1 1 calc R . .
C23 C 0.6594(2) 0.28192(7) 0.63831(12) 0.0588(4) Uani 1 1 d . . .
H23 H 0.7344 0.3069 0.6900 0.071 Uiso 1 1 calc R . .
C21 C 0.5326(2) 0.18298(7) 0.58702(12) 0.0615(4) Uani 1 1 d . . .
H21 H 0.5228 0.1425 0.6048 0.074 Uiso 1 1 calc R . .
C19 C 0.5634(2) 0.30463(6) 0.53641(12) 0.0538(3) Uani 1 1 d . . .
F18 F 0.73354(15) 0.20062(5) 0.76007(8) 0.0876(3) Uani 1 1 d . . .
C16 C 0.15519(19) 0.27818(7) 0.16676(11) 0.0524(3) Uani 1 1 d . . .
H16 H 0.1542 0.3202 0.1635 0.063 Uiso 1 1 calc R . .
C13 C 0.4396(2) 0.20601(6) 0.48627(12) 0.0534(3) Uani 1 1 d . . .
H13 H 0.3652 0.1803 0.4357 0.064 Uiso 1 1 calc R . .
N11 N 0.06086(16) 0.24974(6) 0.07710(9) 0.0549(3) Uani 1 1 d . . .
C10 C 0.3536(2) 0.29170(6) 0.34846(11) 0.0525(3) Uani 1 1 d . . .
C9 C 0.25331(19) 0.25328(7) 0.26296(11) 0.0533(3) Uani 1 1 d . . .
H9 H 0.2549 0.2116 0.2728 0.064 Uiso 1 1 calc R . .
O5 O 0.58018(19) 0.36343(5) 0.51701(9) 0.0794(4) Uani 1 1 d . . .
H5 H 0.5231 0.3714 0.4538 0.119 Uiso 1 1 calc R . .
O3 O 0.36299(17) 0.34790(5) 0.33441(9) 0.0750(3) Uani 1 1 d . . .
C2 C 0.45253(18) 0.26622(6) 0.45719(11) 0.0482(3) Uani 1 1 d . . .
C29 C 0.5067(3) 0.58326(7) 1.22304(14) 0.0745(5) Uani 1 1 d . . .
H29A H 0.5788 0.5873 1.1717 0.112 Uiso 1 1 calc R . .
H29B H 0.5726 0.5982 1.2939 0.112 Uiso 1 1 calc R . .
H29C H 0.3978 0.6061 1.1973 0.112 Uiso 1 1 calc R . .
C28 C 0.5388(3) 0.49160(9) 1.33835(13) 0.0817(5) Uani 1 1 d . . .
H28A H 0.4969 0.4506 1.3357 0.123 Uiso 1 1 calc R . .
H28B H 0.5016 0.5132 1.3948 0.123 Uiso 1 1 calc R . .
H28C H 0.6677 0.4919 1.3545 0.123 Uiso 1 1 calc R . .
C27 C -0.0689(2) 0.53147(7) 0.63864(11) 0.0607(4) Uani 1 1 d . . .
C25 C 0.1055(2) 0.55375(6) 0.81755(12) 0.0584(4) Uani 1 1 d . . .
H25 H 0.1686 0.5815 0.8690 0.070 Uiso 1 1 calc R . .
C22 C 0.0221(2) 0.57375(7) 0.71317(12) 0.0668(4) Uani 1 1 d . . .
H22 H 0.0269 0.6141 0.6936 0.080 Uiso 1 1 calc R . .
C20 C 0.36323(19) 0.48989(6) 1.14771(11) 0.0501(3) Uani 1 1 d . . .
H20 H 0.3417 0.4495 1.1606 0.060 Uiso 1 1 calc R . .
C17 C -0.0832(2) 0.47244(7) 0.66353(11) 0.0592(4) Uani 1 1 d . . .
H17 H -0.1477 0.4456 0.6108 0.071 Uiso 1 1 calc R . .
C15 C 0.0009(2) 0.45278(6) 0.76979(11) 0.0502(3) Uani 1 1 d . . .
C14 C 0.09932(18) 0.49361(6) 0.84944(10) 0.0459(3) Uani 1 1 d . . .
N12 N 0.46312(16) 0.52048(5) 1.23234(9) 0.0557(3) Uani 1 1 d . . .
C8 C 0.18677(18) 0.47130(6) 0.96231(10) 0.0482(3) Uani 1 1 d . . .
O7 O -0.01500(18) 0.39436(5) 0.79399(8) 0.0739(3) Uani 1 1 d . . .
H7 H 0.0323 0.3887 0.8597 0.111 Uiso 1 1 calc R . .
F6 F -0.15144(17) 0.55084(5) 0.53499(7) 0.0907(4) Uani 1 1 d . . .
O1 O 0.16837(16) 0.41607(4) 0.98263(8) 0.0689(3) Uani 1 1 d . . .
C24 C 0.6412(2) 0.22252(7) 0.66061(12) 0.0599(4) Uani 1 1 d . . .
C4 C 0.28810(18) 0.51086(6) 1.04356(10) 0.0490(3) Uani 1 1 d . . .
H4 H 0.3035 0.5510 1.0262 0.059 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
C30 0.0782(12) 0.0669(10) 0.0600(9) -0.0141(7) 0.0121(8) -0.0132(8)
C26 0.0653(11) 0.0825(11) 0.0503(8) 0.0060(7) 0.0064(7) -0.0169(8)
C23 0.0530(9) 0.0647(9) 0.0532(8) -0.0128(7) 0.0042(7) 0.0011(7)
C21 0.0618(10) 0.0566(9) 0.0654(9) 0.0040(7) 0.0153(8) 0.0027(7)
C19 0.0529(9) 0.0497(8) 0.0558(8) -0.0094(6) 0.0088(7) 0.0009(6)
F18 0.0925(8) 0.0921(8) 0.0640(6) 0.0116(5) -0.0044(5) 0.0090(6)
C16 0.0483(8) 0.0581(8) 0.0509(7) -0.0061(6) 0.0132(6) -0.0073(6)
C13 0.0490(8) 0.0523(8) 0.0577(8) -0.0084(6) 0.0120(6) -0.0037(6)
N11 0.0551(7) 0.0621(7) 0.0460(6) -0.0051(5) 0.0105(5) -0.0108(6)
C10 0.0473(8) 0.0528(8) 0.0547(8) -0.0086(6) 0.0088(6) 0.0006(6)
C9 0.0526(9) 0.0539(8) 0.0519(8) -0.0080(6) 0.0112(6) -0.0047(6)
O5 0.0980(10) 0.0494(6) 0.0710(7) -0.0087(5) -0.0128(7) -0.0079(6)
O3 0.0875(9) 0.0492(6) 0.0705(7) -0.0039(5) -0.0104(6) -0.0027(5)
C2 0.0430(8) 0.0484(7) 0.0522(7) -0.0087(5) 0.0112(6) 0.0019(6)
C29 0.0826(12) 0.0650(10) 0.0702(10) -0.0130(8) 0.0099(9) -0.0166(9)
C28 0.0834(13) 0.0923(13) 0.0536(9) 0.0049(8) -0.0099(8) -0.0099(10)
C27 0.0647(10) 0.0669(10) 0.0443(7) 0.0012(6) 0.0030(7) -0.0004(8)
C25 0.0655(10) 0.0511(8) 0.0519(8) -0.0054(6) 0.0040(7) -0.0064(7)
C22 0.0814(12) 0.0535(8) 0.0568(8) 0.0055(7) 0.0030(8) -0.0060(8)
C20 0.0464(8) 0.0506(8) 0.0515(7) -0.0060(6) 0.0095(6) 0.0000(6)
C17 0.0653(10) 0.0601(9) 0.0478(7) -0.0119(6) 0.0068(7) -0.0043(7)
C15 0.0547(8) 0.0460(7) 0.0490(7) -0.0077(5) 0.0120(6) -0.0002(6)
C14 0.0454(8) 0.0461(7) 0.0456(7) -0.0063(5) 0.0108(6) 0.0008(6)
N12 0.0533(8) 0.0605(7) 0.0485(6) -0.0044(5) 0.0049(5) -0.0053(6)
C8 0.0482(8) 0.0474(7) 0.0480(7) -0.0049(5) 0.0108(6) 0.0042(6)
O7 0.1037(10) 0.0489(6) 0.0592(6) -0.0066(5) 0.0041(6) -0.0136(6)
F6 0.1153(9) 0.0887(7) 0.0504(5) 0.0086(4) -0.0094(5) -0.0046(6)
O1 0.0903(8) 0.0460(6) 0.0582(6) -0.0004(4) -0.0021(5) -0.0022(5)
C24 0.0533(9) 0.0720(10) 0.0510(8) 0.0009(7) 0.0078(7) 0.0093(7)
C4 0.0499(8) 0.0493(7) 0.0462(7) -0.0033(5) 0.0101(6) 0.0014(6)

_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
C30 N11 1.445(2) . ?
C26 N11 1.447(2) . ?
C23 C24 1.358(2) . ?
C23 C19 1.393(2) . ?
C21 C13 1.378(2) . ?
C21 C24 1.383(2) . ?
C19 O5 1.3359(17) . ?
C19 C2 1.4125(19) . ?
F18 C24 1.3550(17) . ?
C16 N11 1.3279(18) . ?
C16 C9 1.362(2) . ?
C13 C2 1.3914(19) . ?
C10 O3 1.2603(17) . ?
C10 C9 1.4272(19) . ?
C10 C2 1.490(2) . ?
C29 N12 1.4408(19) . ?
C28 N12 1.454(2) . ?
C27 C17 1.354(2) . ?
C27 F6 1.3600(17) . ?
C27 C22 1.378(2) . ?
C25 C22 1.374(2) . ?
C25 C14 1.3937(18) . ?
C20 N12 1.3231(17) . ?
C20 C4 1.3660(19) . ?
C17 C15 1.392(2) . ?
C15 O7 1.3406(16) . ?
C15 C14 1.4118(18) . ?
C14 C8 1.4859(18) . ?
C8 O1 1.2636(16) . ?
C8 C4 1.4138(18) . ?

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
C24 C23 C19 118.68(13) . . ?
C13 C21 C24 117.22(14) . . ?
O5 C19 C23 117.74(13) . . ?
O5 C19 C2 121.78(13) . . ?
C23 C19 C2 120.49(13) . . ?
N11 C16 C9 127.85(14) . . ?
C21 C13 C2 122.64(13) . . ?
C16 N11 C30 121.46(13) . . ?
C16 N11 C26 121.24(13) . . ?
C30 N11 C26 117.18(12) . . ?
O3 C10 C9 121.42(14) . . ?
O3 C10 C2 117.87(12) . . ?
C9 C10 C2 120.71(13) . . ?
C16 C9 C10 119.45(14) . . ?
C13 C2 C19 117.53(13) . . ?
C13 C2 C10 123.26(12) . . ?
C19 C2 C10 119.19(13) . . ?
C17 C27 F6 118.64(13) . . ?
C17 C27 C22 123.72(14) . . ?
F6 C27 C22 117.62(14) . . ?
C22 C25 C14 122.65(13) . . ?
C25 C22 C27 117.22(14) . . ?
N12 C20 C4 127.38(13) . . ?
C27 C17 C15 118.51(13) . . ?
O7 C15 C17 118.13(12) . . ?
O7 C15 C14 121.31(12) . . ?
C17 C15 C14 120.55(12) . . ?
C25 C14 C15 117.33(12) . . ?
C25 C14 C8 123.40(12) . . ?
C15 C14 C8 119.25(12) . . ?
C20 N12 C29 121.76(12) . . ?
C20 N12 C28 121.34(13) . . ?
C29 N12 C28 116.87(13) . . ?
O1 C8 C4 121.49(12) . . ?
O1 C8 C14 117.87(11) . . ?
C4 C8 C14 120.64(12) . . ?
F18 C24 C23 118.60(14) . . ?
F18 C24 C21 117.99(14) . . ?
C23 C24 C21 123.41(14) . . ?
C20 C4 C8 119.76(13) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.081
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1470381'
_audit_update_record             
;
2016-03-24 deposited with the CCDC.
2016-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H15 N O3'
_chemical_formula_sum            'C12 H15 N O3'
_chemical_formula_weight         221.25

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   7.4266(15)
_cell_length_b                   11.889(2)
_cell_length_c                   13.141(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.20(3)
_cell_angle_gamma                90.00
_cell_volume                     1134.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8284
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block
_exptl_crystal_colour            colorle
_exptl_crystal_size_max          0.485
_exptl_crystal_size_mid          0.403
_exptl_crystal_size_min          0.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10443
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2568
_reflns_number_gt                1905
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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. 
;

_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)+(0.1017P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2568
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1486
_refine_ls_wR_factor_gt          0.1311
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.002
_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
O3 O 0.12888(16) 0.92324(9) 0.07854(8) 0.0598(3) Uani 1 1 d . . .
C5 C 0.17103(16) 0.90774(10) 0.39925(10) 0.0401(3) Uani 1 1 d . . .
O2 O 0.04658(15) 0.72077(8) 0.37844(9) 0.0583(3) Uani 1 1 d . . .
C6 C 0.18973(17) 0.90095(10) 0.51294(10) 0.0441(3) Uani 1 1 d . . .
C2 C 0.13563(17) 0.91254(11) 0.18229(10) 0.0447(3) Uani 1 1 d . . .
C3 C 0.08360(18) 0.81753(11) 0.22883(11) 0.0451(3) Uani 1 1 d . . .
C4 C 0.10009(16) 0.81501(10) 0.33636(11) 0.0419(3) Uani 1 1 d . . .
O1 O 0.13757(17) 0.81159(8) 0.55065(9) 0.0648(3) Uani 1 1 d . . .
N1 N 0.34706(15) 1.06040(9) 0.75493(9) 0.0459(3) Uani 1 1 d . . .
C8 C 0.28550(18) 0.98271(12) 0.68398(11) 0.0445(3) Uani 1 1 d . . .
C11 C 0.21920(18) 1.00295(11) 0.34762(11) 0.0458(3) Uani 1 1 d . . .
C7 C 0.26618(18) 0.99182(11) 0.57861(10) 0.0450(3) Uani 1 1 d . . .
C12 C 0.2024(2) 1.00683(11) 0.24224(11) 0.0490(3) Uani 1 1 d . . .
C10 C 0.3998(2) 1.17107(12) 0.72512(13) 0.0526(4) Uani 1 1 d . . .
C9 C 0.3678(3) 1.03777(15) 0.86507(12) 0.0573(4) Uani 1 1 d . . .
C1 C 0.0681(3) 0.83035(15) 0.01299(14) 0.0711(5) Uani 1 1 d . . .
H1A H 0.1529 0.7690 0.0311 0.107 Uiso 1 1 calc R . .
H1B H 0.0619 0.8514 -0.0582 0.107 Uiso 1 1 calc R . .
H1C H -0.0518 0.8076 0.0216 0.107 Uiso 1 1 calc R . .
H4 H 0.041(2) 0.7553(13) 0.1890(13) 0.051(4) Uiso 1 1 d . . .
H6 H 0.253(2) 0.9145(14) 0.7110(13) 0.052(4) Uiso 1 1 d . . .
H13 H 0.303(2) 1.0592(15) 0.5492(12) 0.051(4) Uiso 1 1 d . . .
H15 H 0.242(2) 1.0706(15) 0.2070(14) 0.063(4) Uiso 1 1 d . . .
H14 H 0.267(2) 1.0701(15) 0.3896(13) 0.060(4) Uiso 1 1 d . . .
H8 H 0.304(3) 1.0890(19) 0.8963(17) 0.085(6) Uiso 1 1 d . . .
H12 H 0.303(2) 1.2052(16) 0.6750(15) 0.067(5) Uiso 1 1 d . . .
H11 H 0.440(3) 1.2145(18) 0.7855(19) 0.087(6) Uiso 1 1 d . . .
H7 H 0.328(4) 0.962(2) 0.875(2) 0.118(8) Uiso 1 1 d . . .
H10 H 0.504(3) 1.1646(16) 0.6908(16) 0.073(5) Uiso 1 1 d . . .
H9 H 0.493(3) 1.0496(18) 0.8997(17) 0.085(6) Uiso 1 1 d . . .
H5 H 0.070(3) 0.742(2) 0.450(2) 0.106(8) Uiso 1 1 d . . .

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
O3 0.0824(7) 0.0561(6) 0.0389(6) -0.0009(4) 0.0081(5) -0.0081(5)
C5 0.0407(6) 0.0377(6) 0.0419(7) 0.0002(5) 0.0084(5) 0.0019(5)
O2 0.0787(7) 0.0407(5) 0.0551(7) 0.0016(4) 0.0135(5) -0.0142(5)
C6 0.0482(7) 0.0400(6) 0.0446(8) 0.0023(5) 0.0109(5) 0.0032(5)
C2 0.0460(7) 0.0473(7) 0.0394(7) 0.0001(5) 0.0058(5) 0.0033(5)
C3 0.0464(7) 0.0407(6) 0.0462(8) -0.0062(5) 0.0048(5) -0.0018(5)
C4 0.0413(6) 0.0357(6) 0.0485(8) 0.0018(5) 0.0092(5) 0.0012(5)
O1 0.1003(9) 0.0475(6) 0.0477(6) 0.0050(4) 0.0186(6) -0.0141(5)
N1 0.0543(6) 0.0454(6) 0.0385(6) -0.0002(4) 0.0108(4) 0.0058(5)
C8 0.0483(7) 0.0423(7) 0.0440(8) 0.0004(5) 0.0120(5) 0.0047(5)
C11 0.0537(7) 0.0379(6) 0.0451(8) -0.0019(5) 0.0087(5) -0.0054(5)
C7 0.0490(7) 0.0436(7) 0.0427(8) 0.0013(5) 0.0102(5) 0.0000(5)
C12 0.0595(8) 0.0418(7) 0.0451(8) 0.0042(5) 0.0095(6) -0.0061(6)
C10 0.0607(9) 0.0454(7) 0.0504(9) -0.0014(6) 0.0091(7) 0.0020(6)
C9 0.0730(10) 0.0586(9) 0.0407(8) 0.0002(6) 0.0129(7) 0.0077(8)
C1 0.1022(13) 0.0644(10) 0.0465(9) -0.0115(7) 0.0150(8) -0.0055(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
O3 C2 1.3596(17) . ?
O3 C1 1.4148(19) . ?
C5 C11 1.4045(18) . ?
C5 C4 1.4114(18) . ?
C5 C6 1.4731(19) . ?
O2 C4 1.3462(16) . ?
C6 O1 1.2671(16) . ?
C6 C7 1.4238(18) . ?
C2 C3 1.3782(19) . ?
C2 C12 1.3995(19) . ?
C3 C4 1.393(2) . ?
N1 C8 1.3234(18) . ?
N1 C9 1.4482(19) . ?
N1 C10 1.4503(19) . ?
C8 C7 1.3659(19) . ?
C11 C12 1.365(2) . ?

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
C2 O3 C1 118.48(12) . . ?
C11 C5 C4 116.64(12) . . ?
C11 C5 C6 123.72(11) . . ?
C4 C5 C6 119.65(11) . . ?
O1 C6 C7 120.99(13) . . ?
O1 C6 C5 118.13(11) . . ?
C7 C6 C5 120.88(11) . . ?
O3 C2 C3 124.56(12) . . ?
O3 C2 C12 115.03(12) . . ?
C3 C2 C12 120.40(13) . . ?
C2 C3 C4 119.68(12) . . ?
O2 C4 C3 117.67(11) . . ?
O2 C4 C5 121.04(12) . . ?
C3 C4 C5 121.29(11) . . ?
C8 N1 C9 121.50(12) . . ?
C8 N1 C10 121.05(12) . . ?
C9 N1 C10 117.44(12) . . ?
N1 C8 C7 127.27(13) . . ?
C12 C11 C5 122.65(12) . . ?
C8 C7 C6 119.83(13) . . ?
C11 C12 C2 119.32(12) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1470382'
_audit_update_record             
;
2016-03-24 deposited with the CCDC.
2016-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H12 F N O2'
_chemical_formula_sum            'C11 H12 F N O2'
_chemical_formula_weight         209.22

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)/n
_symmetry_space_group_name_Hall  '-P 2yn'


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

_cell_length_a                   9.0682(18)
_cell_length_b                   10.390(2)
_cell_length_c                   11.580(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.17(3)
_cell_angle_gamma                90.00
_cell_volume                     1030.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7841
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.658
_exptl_crystal_size_mid          0.525
_exptl_crystal_size_min          0.515
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9861
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         27.47
_reflns_number_total             2337
_reflns_number_gt                1768
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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. 
;

_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)+(0.0949P)²+0.0905P] 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         2337
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1566
_refine_ls_wR_factor_gt          0.1456
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
C6 C 0.19055(15) 0.78105(14) 0.32143(12) 0.0364(3) Uani 1 1 d . . .
C7 C 0.07234(17) 0.81859(14) 0.37919(13) 0.0388(3) Uani 1 1 d . . .
C5 C 0.18298(18) 0.82322(16) 0.20474(14) 0.0431(4) Uani 1 1 d . . .
C1 C 0.31608(18) 0.70073(15) 0.38533(14) 0.0428(4) Uani 1 1 d . . .
C8 C -0.06542(17) 0.88395(14) 0.31075(14) 0.0392(3) Uani 1 1 d . . .
C2 C 0.4284(2) 0.66569(17) 0.33258(16) 0.0509(4) Uani 1 1 d . . .
C3 C 0.4191(2) 0.70868(18) 0.21817(16) 0.0522(4) Uani 1 1 d . . .
C9 C -0.17292(18) 0.91808(15) 0.36537(15) 0.0423(4) Uani 1 1 d . . .
C4 C 0.29618(19) 0.78630(17) 0.15702(14) 0.0487(4) Uani 1 1 d . . .
C11 C -0.3629(2) 1.0128(2) 0.18757(18) 0.0667(6) Uani 1 1 d . . .
H11A H -0.2939 1.0764 0.1736 0.100 Uiso 1 1 calc R . .
H11B H -0.4662 1.0479 0.1670 0.100 Uiso 1 1 calc R . .
H11C H -0.3647 0.9388 0.1375 0.100 Uiso 1 1 calc R . .
C10 C -0.4092(2) 1.0066(2) 0.3868(2) 0.0637(5) Uani 1 1 d . . .
H10A H -0.3642 0.9729 0.4680 0.096 Uiso 1 1 calc R . .
H10B H -0.5104 0.9692 0.3490 0.096 Uiso 1 1 calc R . .
H10C H -0.4192 1.0984 0.3906 0.096 Uiso 1 1 calc R . .
F1 F 0.28677(14) 0.82917(14) 0.04371(10) 0.0776(4) Uani 1 1 d . . .
N1 N -0.30854(14) 0.97547(13) 0.31489(13) 0.0467(4) Uani 1 1 d . . .
O1 O 0.33129(16) 0.65675(14) 0.49817(11) 0.0628(4) Uani 1 1 d . . .
H1 H 0.2592 0.6840 0.5192 0.094 Uiso 1 1 calc R . .
O2 O 0.09971(14) 0.78873(14) 0.49027(10) 0.0584(4) Uani 1 1 d . . .
H4 H 0.098(2) 0.8772(19) 0.1521(16) 0.053(5) Uiso 1 1 d . . .
H5 H -0.0817(19) 0.9018(16) 0.2303(16) 0.043(4) Uiso 1 1 d . . .
H6 H -0.150(2) 0.9011(18) 0.4448(18) 0.057(5) Uiso 1 1 d . . .
H3 H 0.497(2) 0.6873(19) 0.1845(17) 0.054(5) Uiso 1 1 d . . .
H2 H 0.513(3) 0.615(2) 0.3807(19) 0.074(6) Uiso 1 1 d . . .

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
C6 0.0330(7) 0.0392(8) 0.0379(7) -0.0037(5) 0.0128(6) -0.0035(5)
C7 0.0378(8) 0.0443(8) 0.0369(7) -0.0017(5) 0.0158(6) -0.0063(6)
C5 0.0386(8) 0.0530(9) 0.0396(8) 0.0023(6) 0.0156(6) 0.0069(6)
C1 0.0417(8) 0.0438(8) 0.0411(8) -0.0004(6) 0.0112(6) -0.0013(6)
C8 0.0396(8) 0.0418(8) 0.0407(8) -0.0001(6) 0.0192(6) -0.0015(6)
C2 0.0428(9) 0.0531(10) 0.0542(10) -0.0026(7) 0.0124(7) 0.0115(7)
C3 0.0448(9) 0.0620(11) 0.0546(10) -0.0113(8) 0.0226(7) 0.0075(7)
C9 0.0441(8) 0.0439(8) 0.0439(8) -0.0024(6) 0.0212(6) -0.0044(6)
C4 0.0467(9) 0.0630(11) 0.0404(8) -0.0008(7) 0.0199(7) 0.0050(7)
C11 0.0606(11) 0.0782(14) 0.0669(12) 0.0161(9) 0.0287(9) 0.0256(10)
C10 0.0543(10) 0.0735(13) 0.0777(13) -0.0156(10) 0.0412(9) 0.0020(9)
F1 0.0733(8) 0.1207(11) 0.0533(7) 0.0221(6) 0.0402(6) 0.0322(7)
N1 0.0430(7) 0.0485(8) 0.0565(8) -0.0048(6) 0.0270(6) 0.0035(5)
O1 0.0572(8) 0.0809(10) 0.0499(7) 0.0208(6) 0.0169(6) 0.0168(6)
O2 0.0488(7) 0.0893(10) 0.0417(7) 0.0106(6) 0.0211(5) 0.0071(6)

_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
C6 C5 1.401(2) . ?
C6 C1 1.409(2) . ?
C6 C7 1.4898(19) . ?
C7 O2 1.2660(18) . ?
C7 C8 1.414(2) . ?
C5 C4 1.371(2) . ?
C1 O1 1.3480(19) . ?
C1 C2 1.397(2) . ?
C8 C9 1.372(2) . ?
C2 C3 1.374(3) . ?
C3 C4 1.370(2) . ?
C9 N1 1.318(2) . ?
C4 F1 1.3616(19) . ?
C11 N1 1.446(2) . ?
C10 N1 1.4594(19) . ?

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
C5 C6 C1 117.84(13) . . ?
C5 C6 C7 122.46(13) . . ?
C1 C6 C7 119.70(13) . . ?
O2 C7 C8 121.97(13) . . ?
O2 C7 C6 117.52(13) . . ?
C8 C7 C6 120.50(12) . . ?
C4 C5 C6 119.70(15) . . ?
O1 C1 C2 118.57(14) . . ?
O1 C1 C6 121.17(14) . . ?
C2 C1 C6 120.26(14) . . ?
C9 C8 C7 119.77(14) . . ?
C3 C2 C1 120.94(16) . . ?
C4 C3 C2 118.15(15) . . ?
N1 C9 C8 127.83(15) . . ?
F1 C4 C5 118.61(15) . . ?
F1 C4 C3 118.28(14) . . ?
C5 C4 C3 123.12(15) . . ?
C9 N1 C11 121.99(13) . . ?
C9 N1 C10 120.97(15) . . ?
C11 N1 C10 117.02(15) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.101
