# 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_chiba402
_database_code_depnum_ccdc_archive 'CCDC 1503986'
_audit_update_record             
;
2016-09-12 deposited with the CCDC.
2016-12-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 F N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         281.32

_chemical_melting_point          ?

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

_cell_length_a                   9.7930(7)
_cell_length_b                   9.5921(6)
_cell_length_c                   15.8816(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.943(3)
_cell_angle_gamma                90
_cell_volume                     1473.71(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7723
_cell_measurement_theta_min      2.4888
_cell_measurement_theta_max      29.0708
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.280
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592

_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            28196
_diffrn_reflns_av_R_equivalents  0.1162
_diffrn_reflns_av_unetI/netI     0.0775
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         29.24
_diffrn_reflns_theta_full        29.24
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
;

_reflns_number_total             3968
_reflns_number_gt                2912
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0954
_refine_ls_R_factor_gt           0.0648
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1695
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_number_reflns         3968
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0789P)²+0.7909P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.391
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.73480(17) 0.23697(17) -0.03890(10) 0.0129(3) Uani d . . . 1 . .
C C2 0.98063(18) 0.23844(18) -0.01574(11) 0.0148(4) Uani d . . . 1 . .
C C3 0.97795(17) 0.34438(18) 0.03891(11) 0.0148(4) Uani d . . . 1 . .
H H3 1.0574 0.4005 0.0557 0.018 Uiso calc U . R 1 . .
C C4 0.84976(17) 0.37105(17) 0.07184(10) 0.0128(3) Uani d . . . 1 . .
C C5 0.62562(19) 0.12304(19) -0.04522(11) 0.0168(4) Uani d . . . 1 . .
H H5A 0.5327 0.1656 -0.0497 0.02 Uiso calc U . R 1 . .
H H5B 0.6286 0.0664 -0.097 0.02 Uiso calc U . R 1 . .
C C6 0.70297(17) 0.33207(18) -0.11705(11) 0.0137(4) Uani d . . . 1 . .
C C7 0.65717(18) 0.46818(19) -0.11023(11) 0.0162(4) Uani d . . . 1 . .
H H7 0.6463 0.5045 -0.056 0.019 Uiso calc U . R 1 . .
C C8 0.62714(19) 0.5516(2) -0.18271(12) 0.0196(4) Uani d . . . 1 . .
H H8 0.597 0.6449 -0.1777 0.024 Uiso calc U . R 1 . .
C C9 0.64123(19) 0.4982(2) -0.26222(12) 0.0217(4) Uani d . . . 1 . .
H H9 0.6216 0.5553 -0.3115 0.026 Uiso calc U . R 1 . .
C C10 0.6839(2) 0.3618(2) -0.26970(12) 0.0217(4) Uani d . . . 1 . .
H H10 0.6917 0.3248 -0.3242 0.026 Uiso calc U . R 1 . .
C C11 0.71526(19) 0.2790(2) -0.19747(11) 0.0181(4) Uani d . . . 1 . .
H H11 0.7453 0.1856 -0.2028 0.022 Uiso calc U . R 1 . .
C C12 1.10315(19) 0.1836(2) -0.04954(13) 0.0217(4) Uani d . . . 1 . .
H H12A 1.0901 0.1959 -0.1115 0.033 Uiso calc U . R 1 . .
H H12B 1.1143 0.0842 -0.0358 0.033 Uiso calc U . R 1 . .
H H12C 1.1859 0.2343 -0.0236 0.033 Uiso calc U . R 1 . .
C C13 0.84752(18) 0.46365(17) 0.14704(11) 0.0139(3) Uani d . . . 1 . .
C C14 0.72114(19) 0.52229(18) 0.15921(11) 0.0169(4) Uani d . . . 1 . .
H H14 0.6403 0.5035 0.1195 0.02 Uiso calc U . R 1 . .
C C15 0.7130(2) 0.60749(19) 0.22862(12) 0.0206(4) Uani d . . . 1 . .
H H15 0.6268 0.6468 0.2365 0.025 Uiso calc U . R 1 . .
C C16 0.8312(2) 0.6354(2) 0.28680(12) 0.0219(4) Uani d . . . 1 . .
H H16 0.8256 0.6932 0.3347 0.026 Uiso calc U . R 1 . .
C C17 0.9572(2) 0.5791(2) 0.27510(12) 0.0224(4) Uani d . . . 1 . .
H H17 1.0377 0.5984 0.315 0.027 Uiso calc U . R 1 . .
C C18 0.96623(19) 0.49416(19) 0.20475(11) 0.0184(4) Uani d . . . 1 . .
H H18 1.053 0.4572 0.1962 0.022 Uiso calc U . R 1 . .
F F1 0.64978(11) 0.03775(11) 0.02693(7) 0.0222(3) Uani d . . . 1 . .
N N1 0.73394(15) 0.31387(15) 0.03913(9) 0.0141(3) Uani d . . . 1 . .
O O1 0.86401(12) 0.16293(12) -0.04316(8) 0.0157(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.443(2) ?
C1 O1 . 1.462(2) ?
C1 C5 . 1.521(2) ?
C1 C6 . 1.533(2) ?
C2 C3 . 1.339(2) ?
C2 O1 . 1.365(2) ?
C2 C12 . 1.485(2) ?
C3 C4 . 1.456(2) ?
C4 N1 . 1.294(2) ?
C4 C13 . 1.491(2) ?
C5 F1 . 1.398(2) ?
C6 C7 . 1.390(2) ?
C6 C11 . 1.398(2) ?
C7 C8 . 1.395(2) ?
C8 C9 . 1.389(3) ?
C9 C10 . 1.384(3) ?
C10 C11 . 1.390(3) ?
C13 C18 . 1.395(2) ?
C13 C14 . 1.400(2) ?
C14 C15 . 1.385(2) ?
C15 C16 . 1.390(3) ?
C16 C17 . 1.386(3) ?
C17 C18 . 1.397(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 O1 . . 114.12(13) ?
N1 C1 C5 . . 109.02(13) ?
O1 C1 C5 . . 104.63(13) ?
N1 C1 C6 . . 111.32(13) ?
O1 C1 C6 . . 108.68(13) ?
C5 C1 C6 . . 108.77(13) ?
C3 C2 O1 . . 120.63(15) ?
C3 C2 C12 . . 126.99(16) ?
O1 C2 C12 . . 112.30(15) ?
C2 C3 C4 . . 118.10(16) ?
N1 C4 C3 . . 122.17(15) ?
N1 C4 C13 . . 116.93(15) ?
C3 C4 C13 . . 120.88(15) ?
F1 C5 C1 . . 109.80(13) ?
C7 C6 C11 . . 119.22(16) ?
C7 C6 C1 . . 121.55(15) ?
C11 C6 C1 . . 119.18(15) ?
C6 C7 C8 . . 120.22(16) ?
C9 C8 C7 . . 120.04(17) ?
C10 C9 C8 . . 120.03(17) ?
C9 C10 C11 . . 120.02(17) ?
C10 C11 C6 . . 120.44(17) ?
C18 C13 C14 . . 119.30(16) ?
C18 C13 C4 . . 122.45(16) ?
C14 C13 C4 . . 118.24(15) ?
C15 C14 C13 . . 120.58(17) ?
C14 C15 C16 . . 119.85(17) ?
C17 C16 C15 . . 120.19(17) ?
C16 C17 C18 . . 120.18(17) ?
C13 C18 C17 . . 119.88(17) ?
C4 N1 C1 . . 116.08(14) ?
C2 O1 C1 . . 114.50(13) ?

####################################################################### 
# 
# 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_chiba398s
_database_code_depnum_ccdc_archive 'CCDC 1503987'
_audit_update_record             
;
2016-09-12 deposited with the CCDC.
2016-12-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 Br F N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         346.19
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   9.5444(5)
_cell_length_b                   10.0871(6)
_cell_length_c                   15.2076(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1464.12(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3835
_cell_measurement_theta_min      2.6787
_cell_measurement_theta_max      26.9480
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696

_exptl_absorpt_coefficient_mu    2.816
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.36
_exptl_absorpt_correction_T_max  0.48

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            13798
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_full        27.97
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             3457
_reflns_number_gt                2551
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_gt          0.0657
_refine_ls_wR_factor_ref         0.0750
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_number_reflns         3457
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.539
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 970 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(11)

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.50456(4) 0.21451(4) 0.35591(7) 0.03709(15) Uani d . . . 1 . .
C C1 0.4523(5) 0.2842(5) 0.6564(3) 0.0272(11) Uani d . . . 1 . .
H H1 0.4822 0.1986 0.6434 0.033 Uiso calc U . R 1 . .
C C2 0.3472(5) 0.3036(5) 0.7179(3) 0.0342(12) Uani d . . . 1 . .
H H2 0.307 0.2311 0.746 0.041 Uiso calc U . R 1 . .
C C3 0.3021(5) 0.4295(6) 0.7377(4) 0.0380(14) Uani d . . . 1 . .
H H3 0.2306 0.4419 0.7785 0.046 Uiso calc U . R 1 . .
C C4 0.3625(5) 0.5370(6) 0.6972(4) 0.0382(15) Uani d . . . 1 . .
H H4 0.3332 0.6222 0.7118 0.046 Uiso calc U . R 1 . .
C C5 0.4665(4) 0.5196(5) 0.6350(4) 0.0308(12) Uani d . . . 1 . .
H H5 0.5055 0.5928 0.6071 0.037 Uiso calc U . R 1 . .
C C6 0.5131(4) 0.3918(5) 0.6141(3) 0.0241(10) Uani d . . . 1 . .
C C7 0.6190(4) 0.3681(4) 0.5445(3) 0.0216(10) Uani d . . . 1 . .
C C8 0.6677(5) 0.4871(4) 0.4928(4) 0.0261(11) Uani d . . . 1 . .
H H8A 0.5911 0.52 0.457 0.031 Uiso calc U . R 1 . .
H H8B 0.6952 0.557 0.533 0.031 Uiso calc U . R 1 . .
C C9 0.7438(4) 0.2018(4) 0.4643(3) 0.0205(10) Uani d . . . 1 . .
C C10 0.6898(4) 0.1634(4) 0.3856(3) 0.0241(11) Uani d . . . 1 . .
C C11 0.7553(5) 0.0720(4) 0.3258(3) 0.0271(11) Uani d . . . 1 . .
H H11 0.844 0.0413 0.3408 0.033 Uiso calc U . R 1 . .
C C12 0.8914(4) 0.1750(4) 0.4895(3) 0.0204(10) Uani d . . . 1 . .
C C13 0.9996(4) 0.2025(4) 0.4304(3) 0.0233(9) Uani d . . . 1 . .
H H13 0.9792 0.2364 0.3749 0.028 Uiso calc U . R 1 . .
C C14 1.1370(5) 0.1792(5) 0.4546(5) 0.0387(14) Uani d . . . 1 . .
H H14 1.2091 0.1963 0.4151 0.046 Uiso calc U . R 1 . .
C C15 1.1679(5) 0.1307(5) 0.5371(5) 0.0451(16) Uani d . . . 1 . .
H H15 1.2606 0.115 0.5528 0.054 Uiso calc U . R 1 . .
C C16 1.0611(6) 0.1052(5) 0.5970(4) 0.0439(16) Uani d . . . 1 . .
H H16 1.0822 0.0729 0.6528 0.053 Uiso calc U . R 1 . .
C C17 0.9226(5) 0.1282(4) 0.5730(3) 0.0287(11) Uani d . . . 1 . .
H H17 0.8508 0.1123 0.613 0.034 Uiso calc U . R 1 . .
F F1 0.7807(2) 0.4545(2) 0.4387(2) 0.0303(6) Uani d . . . 1 . .
N N1 0.6603(4) 0.2506(3) 0.5305(3) 0.0252(9) Uani d . . . 1 . .
O O1 0.7051(4) 0.0310(3) 0.2571(3) 0.0396(9) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C10 . 1.896(4) ?
C1 C2 . 1.385(7) ?
C1 C6 . 1.389(7) ?
C1 H1 . 0.93 ?
C2 C3 . 1.374(7) ?
C2 H2 . 0.93 ?
C3 C4 . 1.374(8) ?
C3 H3 . 0.93 ?
C4 C5 . 1.382(7) ?
C4 H4 . 0.93 ?
C5 C6 . 1.400(6) ?
C5 H5 . 0.93 ?
C6 C7 . 1.483(6) ?
C7 N1 . 1.267(5) ?
C7 C8 . 1.508(6) ?
C8 F1 . 1.395(5) ?
C8 H8A . 0.97 ?
C8 H8B . 0.97 ?
C9 C10 . 1.360(6) ?
C9 N1 . 1.375(6) ?
C9 C12 . 1.485(6) ?
C10 C11 . 1.438(6) ?
C11 O1 . 1.221(6) ?
C11 H11 . 0.93 ?
C12 C17 . 1.386(7) ?
C12 C13 . 1.397(6) ?
C13 C14 . 1.383(6) ?
C13 H13 . 0.93 ?
C14 C15 . 1.378(9) ?
C14 H14 . 0.93 ?
C15 C16 . 1.391(9) ?
C15 H15 . 0.93 ?
C16 C17 . 1.392(7) ?
C16 H16 . 0.93 ?
C17 H17 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 120.3(4) ?
C2 C1 H1 . . 119.9 ?
C6 C1 H1 . . 119.9 ?
C3 C2 C1 . . 120.4(5) ?
C3 C2 H2 . . 119.8 ?
C1 C2 H2 . . 119.8 ?
C4 C3 C2 . . 119.9(5) ?
C4 C3 H3 . . 120.0 ?
C2 C3 H3 . . 120.0 ?
C3 C4 C5 . . 120.5(5) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C4 C5 C6 . . 120.0(5) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C1 C6 C5 . . 118.8(4) ?
C1 C6 C7 . . 119.3(4) ?
C5 C6 C7 . . 121.8(5) ?
N1 C7 C6 . . 118.8(4) ?
N1 C7 C8 . . 124.2(4) ?
C6 C7 C8 . . 117.0(4) ?
F1 C8 C7 . . 110.9(3) ?
F1 C8 H8A . . 109.5 ?
C7 C8 H8A . . 109.5 ?
F1 C8 H8B . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 108.0 ?
C10 C9 N1 . . 121.8(4) ?
C10 C9 C12 . . 122.3(4) ?
N1 C9 C12 . . 115.2(4) ?
C9 C10 C11 . . 125.1(4) ?
C9 C10 Br1 . . 119.0(3) ?
C11 C10 Br1 . . 115.4(3) ?
O1 C11 C10 . . 126.0(4) ?
O1 C11 H11 . . 117.0 ?
C10 C11 H11 . . 117.0 ?
C17 C12 C13 . . 119.9(4) ?
C17 C12 C9 . . 120.1(4) ?
C13 C12 C9 . . 119.9(4) ?
C14 C13 C12 . . 119.7(5) ?
C14 C13 H13 . . 120.2 ?
C12 C13 H13 . . 120.2 ?
C15 C14 C13 . . 120.4(6) ?
C15 C14 H14 . . 119.8 ?
C13 C14 H14 . . 119.8 ?
C14 C15 C16 . . 120.3(5) ?
C14 C15 H15 . . 119.8 ?
C16 C15 H15 . . 119.8 ?
C15 C16 C17 . . 119.6(5) ?
C15 C16 H16 . . 120.2 ?
C17 C16 H16 . . 120.2 ?
C12 C17 C16 . . 120.1(5) ?
C12 C17 H17 . . 120.0 ?
C16 C17 H17 . . 120.0 ?
C7 N1 C9 . . 129.6(4) ?

####################################################################### 
# 
# 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_chiba403
_database_code_depnum_ccdc_archive 'CCDC 1503988'
_audit_update_record             
;
2016-09-12 deposited with the CCDC.
2016-12-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 Br F N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         346.19

_chemical_melting_point          ?

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

_cell_length_a                   11.855(3)
_cell_length_b                   16.440(5)
_cell_length_c                   15.069(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.469(7)
_cell_angle_gamma                90
_cell_volume                     2935.9(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2147
_cell_measurement_theta_min      2.4777
_cell_measurement_theta_max      21.7951
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392

_exptl_absorpt_coefficient_mu    2.808
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.49
_exptl_absorpt_correction_T_max  0.77

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            22656
_diffrn_reflns_av_R_equivalents  0.1530
_diffrn_reflns_av_unetI/netI     0.1453
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_full        26.40
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             5999
_reflns_number_gt                3812
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1304
_refine_ls_R_factor_gt           0.0787
_refine_ls_wR_factor_gt          0.1877
_refine_ls_wR_factor_ref         0.2150
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_number_reflns         5999
_refine_ls_number_parameters     385
_refine_ls_number_restraints     2
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0929P)²+2.2432P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.811
_refine_diff_density_min         -0.757
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.92671(6) 0.15431(4) 0.27970(5) 0.0220(2) Uani d . . . 1 . .
Br Br2 0.57319(6) 0.72080(4) 0.17934(6) 0.0225(2) Uani d . . . 1 . .
C C1 1.1402(6) 0.1616(4) 0.3663(5) 0.0154(15) Uani d . . . 1 . .
H H1 1.1903 0.179 0.4127 0.018 Uiso calc U . R 1 . .
C C2 1.0339(6) 0.2018(4) 0.3592(5) 0.0156(16) Uani d . . . 1 . .
C C3 1.0042(6) 0.2673(4) 0.4106(5) 0.0135(15) Uani d . . . 1 . .
C C4 1.0923(6) 0.3085(4) 0.4674(5) 0.0133(15) Uani d . . . 1 . .
C C5 1.1933(6) 0.3320(4) 0.4317(5) 0.0172(16) Uani d . . . 1 . .
H H5 1.2044 0.3259 0.3698 0.021 Uiso calc U . R 1 . .
C C6 1.2801(6) 0.3650(4) 0.4863(5) 0.0205(17) Uani d . . . 1 . .
H H6 1.3503 0.38 0.4621 0.025 Uiso calc U . R 1 . .
C C7 1.2612(6) 0.3751(4) 0.5750(5) 0.0208(18) Uani d . . . 1 . .
H H7 1.3194 0.3975 0.6119 0.025 Uiso calc U . R 1 . .
C C8 1.1600(7) 0.3536(4) 0.6123(6) 0.0221(18) Uani d . . . 1 . .
H H8 1.1486 0.3618 0.6738 0.027 Uiso calc U . R 1 . .
C C9 1.0744(6) 0.3194(4) 0.5578(5) 0.0166(16) Uani d . . . 1 . .
H H9 1.0046 0.3038 0.5824 0.02 Uiso calc U . R 1 . .
C C10 0.8572(6) 0.3651(4) 0.4540(5) 0.0129(15) Uani d . . . 1 . .
C C11 0.9047(6) 0.4373(4) 0.4370(5) 0.0217(17) Uani d . . . 1 . .
H H11 0.8768 0.4842 0.466 0.026 Uiso calc U . R 1 . .
C C12 0.7569(6) 0.3578(4) 0.5100(5) 0.0154(16) Uani d . . . 1 . .
C C13 0.6747(7) 0.4179(4) 0.5099(5) 0.0207(17) Uani d . . . 1 . .
H H13 0.6827 0.4643 0.4731 0.025 Uiso calc U . R 1 . .
C C14 0.5806(7) 0.4111(4) 0.5628(5) 0.0230(18) Uani d . . . 1 . .
H H14 0.5253 0.4529 0.5631 0.028 Uiso calc U . R 1 . .
C C15 0.5688(7) 0.3425(5) 0.6148(5) 0.0272(19) Uani d . . . 1 . .
H H15 0.5044 0.3366 0.6505 0.033 Uiso calc U . R 1 . .
C C16 0.6503(7) 0.2827(5) 0.6149(6) 0.030(2) Uani d . . . 1 . .
H H16 0.6422 0.236 0.6512 0.036 Uiso calc U . R 1 . .
C C17 0.7424(6) 0.2902(4) 0.5634(5) 0.0197(17) Uani d . . . 1 . .
H H17 0.7977 0.2484 0.5641 0.024 Uiso calc U . R 1 . .
C C18 0.3557(6) 0.6620(4) 0.1354(5) 0.0130(15) Uani d . . . 1 . .
H H18 0.3026 0.6216 0.1175 0.016 Uiso calc U . R 1 . .
C C19 0.4683(6) 0.6368(4) 0.1558(5) 0.0162(16) Uani d . . . 1 . .
C C20 0.5025(6) 0.5557(4) 0.1632(5) 0.0124(15) Uani d . . . 1 . .
C C21 0.4193(6) 0.4885(4) 0.1505(5) 0.0170(16) Uani d . . . 1 . .
C C22 0.3243(6) 0.4847(4) 0.2000(5) 0.0222(18) Uani d . . . 1 . .
H H22 0.3107 0.5257 0.2429 0.027 Uiso calc U . R 1 . .
C C23 0.2470(7) 0.4215(5) 0.1882(6) 0.031(2) Uani d . . . 1 . .
H H23 0.1804 0.42 0.222 0.037 Uiso calc U . R 1 . .
C C24 0.2676(8) 0.3609(4) 0.1272(6) 0.033(2) Uani d . . . 1 . .
H H24 0.2153 0.3176 0.1189 0.04 Uiso calc U . R 1 . .
C C25 0.3649(7) 0.3635(4) 0.0783(6) 0.030(2) Uani d . . . 1 . .
H H25 0.3795 0.3214 0.0369 0.036 Uiso calc U . R 1 . .
C C26 0.4417(6) 0.4275(4) 0.0892(5) 0.0203(17) Uani d . . . 1 . .
H H26 0.5081 0.4293 0.0553 0.024 Uiso calc U . R 1 . .
C C27 0.6555(6) 0.4582(4) 0.2034(5) 0.0166(16) Uani d . . . 1 . .
C C28 0.6128(6) 0.4163(4) 0.2689(5) 0.0148(16) Uani d . . . 1 . .
H H28 0.6434 0.3643 0.2828 0.018 Uiso calc U . R 1 . .
C C29 0.7574(6) 0.4313(4) 0.1562(5) 0.0154(15) Uani d . . . 1 . .
C C30 0.7731(6) 0.4535(4) 0.0678(5) 0.0173(16) Uani d . . . 1 . .
H H30 0.7161 0.4832 0.0363 0.021 Uiso calc U . R 1 . .
C C31 0.8728(6) 0.4320(4) 0.0255(5) 0.0184(16) Uani d . . . 1 . .
H H31 0.8831 0.4465 -0.0348 0.022 Uiso calc U . R 1 . .
C C32 0.9551(6) 0.3900(4) 0.0712(5) 0.0205(17) Uani d . . . 1 . .
H H32 1.0236 0.3771 0.043 0.025 Uiso calc U . R 1 . .
C C33 0.9398(6) 0.3661(4) 0.1577(5) 0.0195(17) Uani d . . . 1 . .
H H33 0.9963 0.335 0.1878 0.023 Uiso calc U . R 1 . .
C C34 0.8423(6) 0.3874(4) 0.2010(5) 0.0148(15) Uani d . . . 1 . .
H H34 0.8332 0.372 0.2611 0.018 Uiso calc U . R 1 . .
F F1 0.9891(4) 0.4461(2) 0.3813(3) 0.0261(11) Uani d . . . 1 . .
F F2 0.5264(3) 0.4452(2) 0.3173(3) 0.0213(10) Uani d . . . 1 . .
N N1 0.8962(5) 0.2926(3) 0.4154(4) 0.0127(13) Uani d . . D 1 . .
H H1N 0.844(5) 0.265(4) 0.389(5) 0.019 Uiso d U . D 1 . .
N N2 0.6119(5) 0.5354(3) 0.1780(4) 0.0150(13) Uani d . . D 1 . .
H H2N 0.662(5) 0.572(3) 0.170(5) 0.023 Uiso d U . D 1 . .
O O1 1.1734(4) 0.1065(3) 0.3179(3) 0.0180(11) Uani d . . . 1 . .
O O2 0.3226(4) 0.7333(3) 0.1394(3) 0.0170(11) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C2 . 1.892(7) ?
Br2 C19 . 1.886(7) ?
C1 O1 . 1.234(8) ?
C1 C2 . 1.424(10) ?
C2 C3 . 1.378(10) ?
C3 N1 . 1.350(9) ?
C3 C4 . 1.495(9) ?
C4 C5 . 1.381(10) ?
C4 C9 . 1.395(10) ?
C5 C6 . 1.409(10) ?
C6 C7 . 1.370(11) ?
C7 C8 . 1.384(11) ?
C8 C9 . 1.407(10) ?
C10 C11 . 1.341(10) ?
C10 N1 . 1.410(9) ?
C10 C12 . 1.481(10) ?
C11 F1 . 1.330(9) ?
C12 C17 . 1.386(10) ?
C12 C13 . 1.387(10) ?
C13 C14 . 1.392(11) ?
C14 C15 . 1.382(11) ?
C15 C16 . 1.379(11) ?
C16 C17 . 1.361(11) ?
C18 O2 . 1.237(8) ?
C18 C19 . 1.424(10) ?
C19 C20 . 1.397(9) ?
C20 N2 . 1.352(9) ?
C20 C21 . 1.489(9) ?
C21 C22 . 1.368(11) ?
C21 C26 . 1.395(10) ?
C22 C23 . 1.394(10) ?
C23 C24 . 1.382(12) ?
C24 C25 . 1.385(13) ?
C25 C26 . 1.398(10) ?
C27 C28 . 1.315(10) ?
C27 N2 . 1.419(8) ?
C27 C29 . 1.485(10) ?
C28 F2 . 1.358(8) ?
C29 C34 . 1.399(9) ?
C29 C30 . 1.399(10) ?
C30 C31 . 1.403(10) ?
C31 C32 . 1.368(10) ?
C32 C33 . 1.377(11) ?
C33 C34 . 1.386(10) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C2 . . 126.2(7) ?
C3 C2 C1 . . 123.9(6) ?
C3 C2 Br1 . . 120.1(5) ?
C1 C2 Br1 . . 115.8(5) ?
N1 C3 C2 . . 121.8(6) ?
N1 C3 C4 . . 118.6(6) ?
C2 C3 C4 . . 119.5(6) ?
C5 C4 C9 . . 120.0(7) ?
C5 C4 C3 . . 120.2(7) ?
C9 C4 C3 . . 119.7(6) ?
C4 C5 C6 . . 120.5(7) ?
C7 C6 C5 . . 118.8(7) ?
C6 C7 C8 . . 122.1(7) ?
C7 C8 C9 . . 119.0(8) ?
C4 C9 C8 . . 119.7(7) ?
C11 C10 N1 . . 121.7(7) ?
C11 C10 C12 . . 121.9(6) ?
N1 C10 C12 . . 116.3(6) ?
F1 C11 C10 . . 122.9(6) ?
C17 C12 C13 . . 118.4(7) ?
C17 C12 C10 . . 120.6(6) ?
C13 C12 C10 . . 121.0(6) ?
C12 C13 C14 . . 121.0(7) ?
C15 C14 C13 . . 119.0(7) ?
C16 C15 C14 . . 120.1(8) ?
C17 C16 C15 . . 120.5(8) ?
C16 C17 C12 . . 121.1(7) ?
O2 C18 C19 . . 124.2(6) ?
C20 C19 C18 . . 124.3(6) ?
C20 C19 Br2 . . 119.7(5) ?
C18 C19 Br2 . . 115.9(5) ?
N2 C20 C19 . . 121.5(6) ?
N2 C20 C21 . . 117.9(6) ?
C19 C20 C21 . . 120.5(6) ?
C22 C21 C26 . . 120.1(7) ?
C22 C21 C20 . . 121.1(7) ?
C26 C21 C20 . . 118.8(7) ?
C21 C22 C23 . . 120.8(8) ?
C24 C23 C22 . . 119.7(8) ?
C23 C24 C25 . . 119.7(7) ?
C24 C25 C26 . . 120.6(8) ?
C21 C26 C25 . . 119.0(8) ?
C28 C27 N2 . . 121.8(7) ?
C28 C27 C29 . . 122.5(6) ?
N2 C27 C29 . . 115.6(6) ?
C27 C28 F2 . . 122.0(6) ?
C34 C29 C30 . . 118.8(7) ?
C34 C29 C27 . . 120.5(7) ?
C30 C29 C27 . . 120.6(6) ?
C29 C30 C31 . . 120.1(7) ?
C32 C31 C30 . . 119.8(7) ?
C31 C32 C33 . . 120.7(7) ?
C32 C33 C34 . . 120.4(7) ?
C33 C34 C29 . . 120.1(7) ?
C3 N1 C10 . . 127.2(6) ?
C20 N2 C27 . . 127.3(6) ?

####################################################################### 
# 
# 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_chiba406s
_database_code_depnum_ccdc_archive 'CCDC 1503989'
_audit_update_record             
;
2016-09-12 deposited with the CCDC.
2016-12-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 F N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         269.27

_chemical_melting_point          ?

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

_cell_length_a                   12.1739(3)
_cell_length_b                   11.0034(3)
_cell_length_c                   9.8232(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.269(2)
_cell_angle_gamma                90
_cell_volume                     1315.85(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7451
_cell_measurement_theta_min      3.6308
_cell_measurement_theta_max      67.0772
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.390
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560

_exptl_absorpt_coefficient_mu    0.828
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.45
_exptl_absorpt_correction_T_max  0.74

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'Incoatec Microfocus Source'
_diffrn_source_type              'Bruker Kappa Duo APEX2'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            11348
_diffrn_reflns_av_R_equivalents  0.0756
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_theta_min         3.63
_diffrn_reflns_theta_max         67.48
_diffrn_reflns_theta_full        67.48
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             2324
_reflns_number_gt                2043
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_gt          0.1431
_refine_ls_wR_factor_ref         0.1508
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_number_reflns         2324
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0980P)²+0.1972P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.367
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.034(3)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.56047(14) 0.46509(15) 0.70221(17) 0.0366(4) Uani d . . . 1 . .
H H1 0.603 0.5315 0.7348 0.044 Uiso calc U . R 1 . .
C C2 0.46645(16) 0.42912(18) 0.7713(2) 0.0458(5) Uani d . . . 1 . .
H H2 0.4447 0.471 0.8513 0.055 Uiso calc U . R 1 . .
C C3 0.40452(15) 0.33250(19) 0.7239(2) 0.0483(5) Uani d . . . 1 . .
H H3 0.3409 0.3076 0.772 0.058 Uiso calc U . R 1 . .
C C4 0.43505(14) 0.27170(17) 0.6061(2) 0.0436(5) Uani d . . . 1 . .
H H4 0.3916 0.2062 0.573 0.052 Uiso calc U . R 1 . .
C C5 0.52890(13) 0.30641(15) 0.53674(18) 0.0357(4) Uani d . . . 1 . .
H H5 0.5502 0.2643 0.4566 0.043 Uiso calc U . R 1 . .
C C6 0.59203(12) 0.40328(14) 0.58487(16) 0.0304(4) Uani d . . . 1 . .
C C7 0.69142(12) 0.43805(14) 0.50991(15) 0.0283(4) Uani d . . . 1 . .
C C8 0.76218(13) 0.54729(14) 0.54070(15) 0.0300(4) Uani d . . . 1 . .
C C9 0.83003(13) 0.43798(14) 0.36438(16) 0.0307(4) Uani d . . . 1 . .
C C10 0.92817(14) 0.35698(17) 0.39684(18) 0.0384(4) Uani d . . . 1 . .
H H10A 0.9218 0.2795 0.3463 0.046 Uiso calc U . R 1 . .
H H10B 0.9969 0.3977 0.3687 0.046 Uiso calc U . R 1 . .
C C11 0.82740(13) 0.47081(14) 0.21528(16) 0.0304(4) Uani d . . . 1 . .
C C12 0.88007(15) 0.57527(17) 0.16968(17) 0.0395(5) Uani d . . . 1 . .
H H12 0.9176 0.6264 0.2323 0.047 Uiso calc U . R 1 . .
C C13 0.87745(17) 0.60437(17) 0.03232(18) 0.0444(5) Uani d . . . 1 . .
H H13 0.9124 0.6763 0.0013 0.053 Uiso calc U . R 1 . .
C C14 0.82444(15) 0.52950(16) -0.05960(18) 0.0399(5) Uani d . . . 1 . .
H H14 0.8231 0.5497 -0.1536 0.048 Uiso calc U . R 1 . .
C C15 0.77313(15) 0.42471(16) -0.01432(17) 0.0393(5) Uani d . . . 1 . .
H H15 0.7367 0.373 -0.0775 0.047 Uiso calc U . R 1 . .
C C16 0.77474(14) 0.39526(15) 0.12231(17) 0.0350(4) Uani d . . . 1 . .
H H16 0.7397 0.3231 0.1528 0.042 Uiso calc U . R 1 . .
F F1 0.93096(8) 0.33419(10) 0.53631(10) 0.0452(4) Uani d . . . 1 . .
N N1 0.73003(10) 0.37856(11) 0.40912(13) 0.0290(4) Uani d . . . 1 . .
O O1 0.75667(11) 0.62286(10) 0.62832(11) 0.0387(4) Uani d . . . 1 . .
O O2 0.84254(9) 0.54674(10) 0.44637(11) 0.0331(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.391(2) ?
C1 C6 . 1.394(2) ?
C2 C3 . 1.383(3) ?
C3 C4 . 1.388(3) ?
C4 C5 . 1.387(2) ?
C5 C6 . 1.395(2) ?
C6 C7 . 1.470(2) ?
C7 N1 . 1.278(2) ?
C7 C8 . 1.509(2) ?
C8 O1 . 1.199(2) ?
C8 O2 . 1.351(2) ?
C9 O2 . 1.4501(19) ?
C9 N1 . 1.4517(19) ?
C9 C11 . 1.509(2) ?
C9 C10 . 1.523(2) ?
C10 F1 . 1.393(2) ?
C11 C16 . 1.389(2) ?
C11 C12 . 1.391(2) ?
C12 C13 . 1.387(2) ?
C13 C14 . 1.380(3) ?
C14 C15 . 1.386(3) ?
C15 C16 . 1.381(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 119.69(17) ?
C3 C2 C1 . . 120.19(18) ?
C2 C3 C4 . . 120.23(17) ?
C5 C4 C3 . . 120.07(18) ?
C4 C5 C6 . . 119.84(17) ?
C1 C6 C5 . . 119.96(15) ?
C1 C6 C7 . . 121.20(15) ?
C5 C6 C7 . . 118.84(15) ?
N1 C7 C6 . . 124.14(14) ?
N1 C7 C8 . . 110.58(13) ?
C6 C7 C8 . . 125.27(14) ?
O1 C8 O2 . . 122.60(14) ?
O1 C8 C7 . . 131.51(15) ?
O2 C8 C7 . . 105.88(12) ?
O2 C9 N1 . . 106.83(12) ?
O2 C9 C11 . . 110.07(12) ?
N1 C9 C11 . . 112.81(13) ?
O2 C9 C10 . . 106.64(13) ?
N1 C9 C10 . . 109.34(13) ?
C11 C9 C10 . . 110.88(13) ?
F1 C10 C9 . . 109.06(14) ?
C16 C11 C12 . . 119.64(15) ?
C16 C11 C9 . . 120.16(14) ?
C12 C11 C9 . . 120.17(14) ?
C13 C12 C11 . . 119.70(16) ?
C14 C13 C12 . . 120.47(17) ?
C13 C14 C15 . . 119.79(16) ?
C16 C15 C14 . . 120.20(16) ?
C15 C16 C11 . . 120.19(16) ?
C7 N1 C9 . . 108.41(13) ?
C8 O2 C9 . . 108.07(11) ?

