# 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.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ketone7

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
8-acety1-1-dimethylaminonaphthalene, 7
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 N O'
_chemical_formula_weight         213.27

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   P21/n

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                   8.3814(2)
_cell_length_b                   10.2345(2)
_cell_length_c                   13.8672(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.897(8)
_cell_angle_gamma                90.00
_cell_volume                     1144.03(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4962
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9854
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Mitegen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5401
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2586
_reflns_number_gt                2297
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_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)+(0.0422P)²+0.3973P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2586
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0998
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
O1 O 0.76895(9) 0.81311(8) 0.10051(6) 0.02057(19) Uani 1 1 d . . .
N1 N 0.96073(11) 0.57444(9) 0.20653(6) 0.0169(2) Uani 1 1 d . . .
C1 C 1.12634(12) 0.58333(10) 0.19664(7) 0.0148(2) Uani 1 1 d . . .
C10 C 1.15157(12) 0.67582(9) 0.12537(7) 0.0136(2) Uani 1 1 d . . .
C8 C 1.04872(13) 0.83900(10) -0.00317(7) 0.0174(2) Uani 1 1 d . . .
H8 H 0.9591 0.8873 -0.0446 0.021 Uiso 1 1 calc R . .
C9 C 1.01807(12) 0.74940(10) 0.06341(7) 0.0142(2) Uani 1 1 d . . .
C2 C 1.25723(13) 0.51099(10) 0.25260(8) 0.0174(2) Uani 1 1 d . . .
H2 H 1.2390 0.4480 0.2988 0.021 Uiso 1 1 calc R . .
C5 C 1.31459(12) 0.69530(10) 0.11551(7) 0.0151(2) Uani 1 1 d . . .
C11 C 0.94188(14) 0.65052(13) 0.29215(8) 0.0254(3) Uani 1 1 d . . .
H11A H 1.0086 0.6109 0.3545 0.038 Uiso 1 1 calc R . .
H11B H 0.8249 0.6513 0.2921 0.038 Uiso 1 1 calc R . .
H11C H 0.9795 0.7403 0.2872 0.038 Uiso 1 1 calc R . .
C12 C 0.89901(14) 0.44061(12) 0.20770(10) 0.0292(3) Uani 1 1 d . . .
H12A H 0.9208 0.3910 0.1522 0.044 Uiso 1 1 calc R . .
H12B H 0.7793 0.4426 0.2003 0.044 Uiso 1 1 calc R . .
H12C H 0.9557 0.3987 0.2714 0.044 Uiso 1 1 calc R . .
C7 C 1.21118(13) 0.86046(10) -0.01108(8) 0.0186(2) Uani 1 1 d . . .
H7 H 1.2303 0.9243 -0.0564 0.022 Uiso 1 1 calc R . .
C13 C 0.83969(12) 0.73059(10) 0.06390(7) 0.0158(2) Uani 1 1 d . . .
C6 C 1.34090(13) 0.78944(10) 0.04629(8) 0.0175(2) Uani 1 1 d . . .
H6 H 1.4496 0.8032 0.0398 0.021 Uiso 1 1 calc R . .
C3 C 1.41874(13) 0.52946(10) 0.24206(8) 0.0181(2) Uani 1 1 d . . .
H3 H 1.5082 0.4786 0.2810 0.022 Uiso 1 1 calc R . .
C4 C 1.44685(12) 0.62005(10) 0.17614(7) 0.0171(2) Uani 1 1 d . . .
H4 H 1.5564 0.6329 0.1708 0.021 Uiso 1 1 calc R . .
C14 C 0.74745(13) 0.62277(12) -0.00186(8) 0.0230(2) Uani 1 1 d . . .
H14A H 0.6479 0.6003 0.0187 0.035 Uiso 1 1 calc R . .
H14B H 0.8192 0.5458 0.0047 0.035 Uiso 1 1 calc R . .
H14C H 0.7152 0.6520 -0.0718 0.035 Uiso 1 1 calc R . .


_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
O1 C13 1.2197(13) . ?
N1 C1 1.4345(12) . ?
N1 C11 1.4641(14) . ?
N1 C12 1.4658(14) . ?
C1 C2 1.3739(14) . ?
C1 C10 1.4255(14) . ?
C10 C5 1.4240(13) . ?
C10 C9 1.4250(13) . ?
C8 C9 1.3745(14) . ?
C8 C7 1.4129(14) . ?
C8 H8 0.9500 . ?
C9 C13 1.5093(13) . ?
C2 C3 1.4135(14) . ?
C2 H2 0.9500 . ?
C5 C6 1.4193(14) . ?
C5 C4 1.4206(14) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C7 C6 1.3673(15) . ?
C7 H7 0.9500 . ?
C13 C14 1.5035(14) . ?
C6 H6 0.9500 . ?
C3 C4 1.3669(15) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
C1 N1 C11 111.47(8) . . ?
C1 N1 C12 114.46(9) . . ?
C11 N1 C12 111.78(9) . . ?
C2 C1 C10 120.15(9) . . ?
C2 C1 N1 123.75(9) . . ?
C10 C1 N1 116.08(8) . . ?
C5 C10 C9 118.93(9) . . ?
C5 C10 C1 119.21(9) . . ?
C9 C10 C1 121.86(9) . . ?
C9 C8 C7 121.15(9) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 119.82(9) . . ?
C8 C9 C13 117.11(9) . . ?
C10 C9 C13 123.03(9) . . ?
C1 C2 C3 120.57(9) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C6 C5 C4 121.85(9) . . ?
C6 C5 C10 119.40(9) . . ?
C4 C5 C10 118.75(9) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C7 C8 120.12(9) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
O1 C13 C14 122.20(9) . . ?
O1 C13 C9 120.57(9) . . ?
C14 C13 C9 115.87(9) . . ?
C7 C6 C5 120.55(9) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C4 C3 C2 120.35(9) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.93(9) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 984760'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ketone8

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
1-dimethylamino-8-isopropylnaphthalene  8
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H19 N O'
_chemical_formula_weight         241.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0032 0.0015 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0108 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pna21

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

_cell_length_a                   9.37(2)
_cell_length_b                   9.34(2)
_cell_length_c                   15.72(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1376(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3424
_cell_measurement_theta_min      1.3
_cell_measurement_theta_max      26.6


_exptl_crystal_description       'block cut from thin needle'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9928
_exptl_absorpt_correction_T_max  0.9971
_exptl_absorpt_process_details   
; 
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_exptl_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      100(2)
_diffrn_source_type              'DLS beamline I19'
_diffrn_source                   synchrotron

_diffrn_radiation_wavelength     0.68890
_diffrn_radiation_collimation    'Confocal mirrors'
_diffrn_radiation_monochromator  'double crystal silicon'

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  CrystalLogic
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_measurement_details      ?

_diffrn_reflns_number            11800
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_sigmaI/netI    0.0512
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         26.50
_reflns_number_total             3086
_reflns_number_gt                2863
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_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. 
 Refined with MERG 4 in SHELX to combine Friedel opposites.
;

_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)+(0.0788P)²+0.1119P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1607
_refine_ls_number_parameters     167
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1347
_refine_ls_wR_factor_gt          0.1335
_refine_ls_goodness_of_fit_ref   1.214
_refine_ls_restrained_S_all      1.213
_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
O1 O 0.3249(2) 0.6642(2) 0.48553(13) 0.0300(5) Uani 1 1 d . . .
N1 N 0.1602(2) 0.5664(2) 0.65193(16) 0.0244(5) Uani 1 1 d . . .
C1 C 0.2619(2) 0.4919(2) 0.70274(16) 0.0179(5) Uani 1 1 d . . .
C2 C 0.2361(3) 0.4493(3) 0.78545(16) 0.0254(6) Uani 1 1 d . . .
H2 H 0.1455 0.4671 0.8104 0.030 Uiso 1 1 calc R . .
C3 C 0.3433(3) 0.3795(3) 0.83328(17) 0.0283(6) Uani 1 1 d . . .
H3 H 0.3222 0.3468 0.8891 0.034 Uiso 1 1 calc R . .
C4 C 0.4763(3) 0.3584(3) 0.80080(17) 0.0258(5) Uani 1 1 d . . .
H4 H 0.5488 0.3171 0.8352 0.031 Uiso 1 1 calc R . .
C5 C 0.5068(3) 0.3983(3) 0.71500(16) 0.0209(5) Uani 1 1 d . . .
C6 C 0.6446(3) 0.3748(3) 0.67851(19) 0.0252(6) Uani 1 1 d . . .
H6 H 0.7197 0.3377 0.7126 0.030 Uiso 1 1 calc R . .
C7 C 0.6689(3) 0.4057(3) 0.5945(2) 0.0288(6) Uani 1 1 d . . .
H7 H 0.7608 0.3900 0.5707 0.035 Uiso 1 1 calc R . .
C8 C 0.5582(3) 0.4608(3) 0.54299(17) 0.0253(5) Uani 1 1 d . . .
H8 H 0.5759 0.4792 0.4845 0.030 Uiso 1 1 calc R . .
C9 C 0.4253(3) 0.4882(2) 0.57627(15) 0.0194(5) Uani 1 1 d . . .
C10 C 0.3968(2) 0.4603(2) 0.66433(15) 0.0166(4) Uani 1 1 d . . .
C11 C 0.1762(3) 0.7223(3) 0.6588(2) 0.0342(7) Uani 1 1 d . . .
H11A H 0.2762 0.7485 0.6493 0.051 Uiso 1 1 calc R . .
H11C H 0.1469 0.7535 0.7157 0.051 Uiso 1 1 calc R . .
H11B H 0.1161 0.7692 0.6160 0.051 Uiso 1 1 calc R . .
C12 C 0.0120(3) 0.5228(4) 0.6662(3) 0.0378(7) Uani 1 1 d . . .
H12B H -0.0208 0.5599 0.7212 0.057 Uiso 1 1 calc R . .
H12C H 0.0059 0.4180 0.6663 0.057 Uiso 1 1 calc R . .
H12A H -0.0484 0.5612 0.6207 0.057 Uiso 1 1 calc R . .
C13 C 0.3148(3) 0.5441(3) 0.51425(16) 0.0228(5) Uani 1 1 d . . .
C14 C 0.2083(3) 0.4368(3) 0.47841(19) 0.0295(6) Uani 1 1 d . . .
H14 H 0.1724 0.3761 0.5263 0.035 Uiso 1 1 calc R . .
C15 C 0.2839(4) 0.3396(4) 0.4143(2) 0.0426(8) Uani 1 1 d . . .
H15C H 0.3616 0.2882 0.4427 0.064 Uiso 1 1 calc R . .
H15A H 0.3229 0.3978 0.3679 0.064 Uiso 1 1 calc R . .
H15B H 0.2155 0.2704 0.3911 0.064 Uiso 1 1 calc R . .
C16 C 0.0807(4) 0.5125(4) 0.4375(3) 0.0459(9) Uani 1 1 d . . .
H16B H 0.1133 0.5683 0.3884 0.069 Uiso 1 1 calc R . .
H16C H 0.0363 0.5766 0.4792 0.069 Uiso 1 1 calc R . .
H16A H 0.0109 0.4411 0.4188 0.069 Uiso 1 1 calc R . .


_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
O1 C13 1.212(4) . ?
N1 C1 1.425(4) . ?
N1 C12 1.464(4) . ?
N1 C11 1.468(5) . ?
C1 C2 1.381(5) . ?
C1 C10 1.431(4) . ?
C2 C3 1.414(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.361(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.428(5) . ?
C4 H4 0.9500 . ?
C5 C10 1.425(4) . ?
C5 C6 1.430(5) . ?
C6 C7 1.371(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.413(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.374(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.434(5) . ?
C9 C13 1.515(4) . ?
C11 H11A 0.9800 . ?
C11 H11C 0.9800 . ?
C11 H11B 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 H12A 0.9800 . ?
C13 C14 1.523(4) . ?
C14 C15 1.530(5) . ?
C14 C16 1.531(5) . ?
C14 H14 1.0000 . ?
C15 H15C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 H16A 0.9800 . ?

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
C1 N1 C12 114.4(2) . . ?
C1 N1 C11 112.0(2) . . ?
C12 N1 C11 111.2(2) . . ?
C2 C1 N1 123.4(2) . . ?
C2 C1 C10 119.5(2) . . ?
N1 C1 C10 117.1(3) . . ?
C1 C2 C3 120.6(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C10 C5 C4 119.3(3) . . ?
C10 C5 C6 119.4(3) . . ?
C4 C5 C6 121.3(2) . . ?
C7 C6 C5 120.2(2) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.5(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 120.2(2) . . ?
C8 C9 C13 116.0(3) . . ?
C10 C9 C13 123.8(2) . . ?
C5 C10 C1 119.1(3) . . ?
C5 C10 C9 118.6(2) . . ?
C1 C10 C9 122.3(2) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11C C11 H11B 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
H12B C12 H12A 109.5 . . ?
H12C C12 H12A 109.5 . . ?
O1 C13 C9 120.3(2) . . ?
O1 C13 C14 121.5(3) . . ?
C9 C13 C14 117.4(2) . . ?
C13 C14 C15 109.3(3) . . ?
C13 C14 C16 111.3(3) . . ?
C15 C14 C16 111.0(3) . . ?
C13 C14 H14 108.4 . . ?
C15 C14 H14 108.4 . . ?
C16 C14 H14 108.4 . . ?
C14 C15 H15C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
H15C C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15C C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
H16B C16 H16A 109.5 . . ?
H16C C16 H16A 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 984761'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ketone9

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
1-dimethylamino-8-(2,2-dimethylpropanoyl)naphthalene 9
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H21 N O'
_chemical_formula_weight         255.35

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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.4848(6)
_cell_length_b                   12.0004(7)
_cell_length_c                   12.0396(8)
_cell_angle_alpha                73.685(5)
_cell_angle_beta                 85.342(6)
_cell_angle_gamma                83.541(6)
_cell_volume                     1442.66(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11944
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Chunk
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_exptl_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      100
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Mitegen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            13798
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.40
_diffrn_reflns_theta_max         27.48

_diffrn_measurement_details      ?

_reflns_number_total             6618
_reflns_number_gt                5418
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_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)+(0.0521P)²+0.1436P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6618
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1059
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_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
O1A O 0.19374(8) 0.08159(6) 0.25045(6) 0.02482(18) Uani 1 1 d . . .
N1A N 0.03907(8) 0.25733(7) 0.04773(7) 0.01839(19) Uani 1 1 d . . .
C1A C -0.08392(10) 0.28618(8) 0.09729(8) 0.0173(2) Uani 1 1 d . . .
C2A C -0.18059(11) 0.35581(9) 0.03392(9) 0.0234(2) Uani 1 1 d . . .
H2A H -0.1649 0.3903 -0.0466 0.028 Uiso 1 1 calc R . .
C3A C -0.30269(11) 0.37712(10) 0.08606(10) 0.0276(2) Uani 1 1 d . . .
H3A H -0.3672 0.4280 0.0412 0.033 Uiso 1 1 calc R . .
C4A C -0.32864(11) 0.32506(10) 0.20057(10) 0.0256(2) Uani 1 1 d . . .
H4A H -0.4128 0.3360 0.2339 0.031 Uiso 1 1 calc R . .
C5A C -0.23136(10) 0.25491(9) 0.27015(9) 0.0194(2) Uani 1 1 d . . .
C6A C -0.25641(11) 0.20366(9) 0.39011(9) 0.0240(2) Uani 1 1 d . . .
H6A H -0.3412 0.2118 0.4231 0.029 Uiso 1 1 calc R . .
C7A C -0.16068(12) 0.14293(9) 0.45858(9) 0.0257(2) Uani 1 1 d . . .
H7A H -0.1791 0.1070 0.5384 0.031 Uiso 1 1 calc R . .
C8A C -0.03424(11) 0.13345(9) 0.41085(9) 0.0222(2) Uani 1 1 d . . .
H8A H 0.0327 0.0941 0.4601 0.027 Uiso 1 1 calc R . .
C9A C -0.00511(10) 0.17991(8) 0.29430(8) 0.0168(2) Uani 1 1 d . . .
C10A C -0.10542(10) 0.23895(8) 0.21993(8) 0.0159(2) Uani 1 1 d . . .
C11A C 0.05031(12) 0.13985(10) 0.03080(9) 0.0261(2) Uani 1 1 d . . .
H11A H -0.0022 0.1401 -0.0330 0.039 Uiso 1 1 calc R . .
H11B H 0.0203 0.0843 0.1020 0.039 Uiso 1 1 calc R . .
H11C H 0.1404 0.1168 0.0121 0.039 Uiso 1 1 calc R . .
C12A C 0.07718(11) 0.34200(10) -0.06028(9) 0.0259(2) Uani 1 1 d . . .
H12A H 0.0198 0.3429 -0.1209 0.039 Uiso 1 1 calc R . .
H12B H 0.1658 0.3200 -0.0842 0.039 Uiso 1 1 calc R . .
H29C H 0.0714 0.4198 -0.0479 0.039 Uiso 1 1 calc R . .
C13A C 0.13634(10) 0.17359(8) 0.25793(8) 0.0174(2) Uani 1 1 d . . .
C14A C 0.20981(10) 0.27776(9) 0.25626(8) 0.0181(2) Uani 1 1 d . . .
C15A C 0.31633(11) 0.29236(10) 0.16100(9) 0.0266(2) Uani 1 1 d . . .
H15A H 0.3724 0.2194 0.1721 0.040 Uiso 1 1 calc R . .
H15B H 0.3668 0.3553 0.1642 0.040 Uiso 1 1 calc R . .
H15C H 0.2784 0.3118 0.0854 0.040 Uiso 1 1 calc R . .
C16A C 0.27001(12) 0.24541(11) 0.37513(10) 0.0298(3) Uani 1 1 d . . .
H16A H 0.3203 0.3080 0.3793 0.045 Uiso 1 1 calc R . .
H16B H 0.3263 0.1727 0.3850 0.045 Uiso 1 1 calc R . .
H16C H 0.2017 0.2349 0.4367 0.045 Uiso 1 1 calc R . .
C17A C 0.12235(11) 0.39083(9) 0.24203(10) 0.0243(2) Uani 1 1 d . . .
H17A H 0.0844 0.4124 0.1663 0.036 Uiso 1 1 calc R . .
H17B H 0.1727 0.4531 0.2472 0.036 Uiso 1 1 calc R . .
H17C H 0.0538 0.3797 0.3034 0.036 Uiso 1 1 calc R . .
O1B O 0.42725(8) 0.71954(7) 0.41608(7) 0.0308(2) Uani 1 1 d . . .
N1B N 0.59119(9) 0.91580(7) 0.26463(7) 0.01991(19) Uani 1 1 d . . .
C1B C 0.71994(10) 0.86308(8) 0.28650(8) 0.0172(2) Uani 1 1 d . . .
C2B C 0.82342(11) 0.92766(9) 0.26992(9) 0.0225(2) Uani 1 1 d . . .
H2B H 0.8102 1.0102 0.2424 0.027 Uiso 1 1 calc R . .
C3B C 0.94872(11) 0.87428(10) 0.29273(9) 0.0247(2) Uani 1 1 d . . .
H3B H 1.0190 0.9206 0.2806 0.030 Uiso 1 1 calc R . .
C4B C 0.96896(11) 0.75598(10) 0.33226(9) 0.0233(2) Uani 1 1 d . . .
H4B H 1.0536 0.7203 0.3475 0.028 Uiso 1 1 calc R . .
C5B C 0.86545(10) 0.68568(9) 0.35086(8) 0.0195(2) Uani 1 1 d . . .
C6B C 0.88694(12) 0.56284(10) 0.39179(9) 0.0262(2) Uani 1 1 d . . .
H6B H 0.9722 0.5273 0.4040 0.031 Uiso 1 1 calc R . .
C7B C 0.78733(13) 0.49473(10) 0.41389(10) 0.0311(3) Uani 1 1 d . . .
H7B H 0.8030 0.4125 0.4429 0.037 Uiso 1 1 calc R . .
C8B C 0.66141(12) 0.54646(9) 0.39363(9) 0.0266(2) Uani 1 1 d . . .
H8B H 0.5923 0.4984 0.4107 0.032 Uiso 1 1 calc R . .
C9B C 0.63560(10) 0.66531(9) 0.34959(8) 0.0187(2) Uani 1 1 d . . .
C10B C 0.73821(10) 0.73885(8) 0.32789(8) 0.0169(2) Uani 1 1 d . . .
C11B C 0.52996(11) 0.95295(10) 0.36423(10) 0.0279(3) Uani 1 1 d . . .
H11X H 0.5718 1.0188 0.3731 0.042 Uiso 1 1 calc R . .
H11Y H 0.5386 0.8880 0.4347 0.042 Uiso 1 1 calc R . .
H11Z H 0.4386 0.9769 0.3513 0.042 Uiso 1 1 calc R . .
C12B C 0.58266(13) 1.01371(10) 0.15928(11) 0.0314(3) Uani 1 1 d . . .
H12X H 0.6204 1.0801 0.1716 0.047 Uiso 1 1 calc R . .
H12Y H 0.4923 1.0362 0.1413 0.047 Uiso 1 1 calc R . .
H12Z H 0.6296 0.9902 0.0945 0.047 Uiso 1 1 calc R . .
C13B C 0.49622(10) 0.70902(9) 0.33268(9) 0.0199(2) Uani 1 1 d . . .
C14B C 0.43654(10) 0.71420(9) 0.21864(9) 0.0211(2) Uani 1 1 d . . .
C15B C 0.32658(11) 0.81157(11) 0.19398(11) 0.0320(3) Uani 1 1 d . . .
H15X H 0.2813 0.8075 0.1273 0.048 Uiso 1 1 calc R . .
H15Y H 0.3614 0.8874 0.1768 0.048 Uiso 1 1 calc R . .
H15Z H 0.2666 0.8022 0.2620 0.048 Uiso 1 1 calc R . .
C16B C 0.38052(12) 0.59597(10) 0.24153(11) 0.0306(3) Uani 1 1 d . . .
H16X H 0.3178 0.5863 0.3077 0.046 Uiso 1 1 calc R . .
H16Y H 0.4500 0.5328 0.2587 0.046 Uiso 1 1 calc R . .
H16Z H 0.3381 0.5936 0.1727 0.046 Uiso 1 1 calc R . .
C17B C 0.53424(11) 0.72792(10) 0.11648(9) 0.0252(2) Uani 1 1 d . . .
H17X H 0.4909 0.7306 0.0465 0.038 Uiso 1 1 calc R . .
H17Y H 0.6002 0.6616 0.1322 0.038 Uiso 1 1 calc R . .
H17Z H 0.5746 0.8004 0.1049 0.038 Uiso 1 1 calc R . .


_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
O1A C13A 1.2193(12) . ?
N1A C1A 1.4246(13) . ?
N1A C12A 1.4655(13) . ?
N1A C11A 1.4707(13) . ?
C1A C2A 1.3728(15) . ?
C1A C10A 1.4341(13) . ?
C2A C3A 1.4086(16) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.3632(16) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.4143(15) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.4174(14) . ?
C5A C10A 1.4227(14) . ?
C6A C7A 1.3603(17) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.4070(16) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.3792(13) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.4279(14) . ?
C9A C13A 1.5116(14) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H29C 0.9800 . ?
C13A C14A 1.5352(14) . ?
C14A C15A 1.5220(14) . ?
C14A C17A 1.5251(14) . ?
C14A C16A 1.5417(14) . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
O1B C13B 1.2165(12) . ?
N1B C1B 1.4366(13) . ?
N1B C12B 1.4679(14) . ?
N1B C11B 1.4696(13) . ?
C1B C2B 1.3727(15) . ?
C1B C10B 1.4288(13) . ?
C2B C3B 1.4079(16) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.3623(16) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.4143(16) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.4148(14) . ?
C5B C10B 1.4257(15) . ?
C6B C7B 1.3617(18) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.4039(18) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.3784(14) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.4294(14) . ?
C9B C13B 1.5060(15) . ?
C11B H11X 0.9800 . ?
C11B H11Y 0.9800 . ?
C11B H11Z 0.9800 . ?
C12B H12X 0.9800 . ?
C12B H12Y 0.9800 . ?
C12B H12Z 0.9800 . ?
C13B C14B 1.5373(14) . ?
C14B C17B 1.5194(15) . ?
C14B C15B 1.5298(16) . ?
C14B C16B 1.5413(15) . ?
C15B H15X 0.9800 . ?
C15B H15Y 0.9800 . ?
C15B H15Z 0.9800 . ?
C16B H16X 0.9800 . ?
C16B H16Y 0.9800 . ?
C16B H16Z 0.9800 . ?
C17B H17X 0.9800 . ?
C17B H17Y 0.9800 . ?
C17B H17Z 0.9800 . ?

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
C1A N1A C12A 114.68(8) . . ?
C1A N1A C11A 111.91(8) . . ?
C12A N1A C11A 109.87(8) . . ?
C2A C1A N1A 123.42(9) . . ?
C2A C1A C10A 119.44(9) . . ?
N1A C1A C10A 117.14(9) . . ?
C1A C2A C3A 121.24(10) . . ?
C1A C2A H2A 119.4 . . ?
C3A C2A H2A 119.4 . . ?
C4A C3A C2A 120.27(10) . . ?
C4A C3A H3A 119.9 . . ?
C2A C3A H3A 119.9 . . ?
C3A C4A C5A 120.55(10) . . ?
C3A C4A H4A 119.7 . . ?
C5A C4A H4A 119.7 . . ?
C4A C5A C6A 120.90(10) . . ?
C4A C5A C10A 119.54(9) . . ?
C6A C5A C10A 119.52(10) . . ?
C7A C6A C5A 120.87(10) . . ?
C7A C6A H6A 119.6 . . ?
C5A C6A H6A 119.6 . . ?
C6A C7A C8A 119.82(10) . . ?
C6A C7A H7A 120.1 . . ?
C8A C7A H7A 120.1 . . ?
C9A C8A C7A 121.59(10) . . ?
C9A C8A H8A 119.2 . . ?
C7A C8A H8A 119.2 . . ?
C8A C9A C10A 119.40(10) . . ?
C8A C9A C13A 115.49(9) . . ?
C10A C9A C13A 124.83(8) . . ?
C5A C10A C9A 118.58(9) . . ?
C5A C10A C1A 118.54(9) . . ?
C9A C10A C1A 122.85(9) . . ?
N1A C11A H11A 109.5 . . ?
N1A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
N1A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
N1A C12A H12A 109.5 . . ?
N1A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
N1A C12A H29C 109.5 . . ?
H12A C12A H29C 109.5 . . ?
H12B C12A H29C 109.5 . . ?
O1A C13A C9A 120.37(9) . . ?
O1A C13A C14A 120.78(9) . . ?
C9A C13A C14A 117.60(8) . . ?
C15A C14A C17A 110.51(9) . . ?
C15A C14A C13A 109.95(8) . . ?
C17A C14A C13A 112.73(8) . . ?
C15A C14A C16A 109.27(9) . . ?
C17A C14A C16A 109.00(9) . . ?
C13A C14A C16A 105.20(8) . . ?
C14A C15A H15A 109.5 . . ?
C14A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C14A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C14A C16A H16A 109.5 . . ?
C14A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
C14A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C14A C17A H17A 109.5 . . ?
C14A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C14A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C1B N1B C12B 113.53(9) . . ?
C1B N1B C11B 111.74(8) . . ?
C12B N1B C11B 109.91(9) . . ?
C2B C1B C10B 119.95(9) . . ?
C2B C1B N1B 122.39(9) . . ?
C10B C1B N1B 117.66(9) . . ?
C1B C2B C3B 121.47(10) . . ?
C1B C2B H2B 119.3 . . ?
C3B C2B H2B 119.3 . . ?
C4B C3B C2B 119.83(10) . . ?
C4B C3B H3B 120.1 . . ?
C2B C3B H3B 120.1 . . ?
C3B C4B C5B 120.81(10) . . ?
C3B C4B H4B 119.6 . . ?
C5B C4B H4B 119.6 . . ?
C4B C5B C6B 120.62(10) . . ?
C4B C5B C10B 119.80(9) . . ?
C6B C5B C10B 119.58(10) . . ?
C7B C6B C5B 121.02(11) . . ?
C7B C6B H6B 119.5 . . ?
C5B C6B H6B 119.5 . . ?
C6B C7B C8B 119.78(10) . . ?
C6B C7B H7B 120.1 . . ?
C8B C7B H7B 120.1 . . ?
C9B C8B C7B 121.58(11) . . ?
C9B C8B H8B 119.2 . . ?
C7B C8B H8B 119.2 . . ?
C8B C9B C10B 119.66(10) . . ?
C8B C9B C13B 115.97(10) . . ?
C10B C9B C13B 124.31(9) . . ?
C5B C10B C1B 118.13(9) . . ?
C5B C10B C9B 118.31(9) . . ?
C1B C10B C9B 123.56(9) . . ?
N1B C11B H11X 109.5 . . ?
N1B C11B H11Y 109.5 . . ?
H11X C11B H11Y 109.5 . . ?
N1B C11B H11Z 109.5 . . ?
H11X C11B H11Z 109.5 . . ?
H11Y C11B H11Z 109.5 . . ?
N1B C12B H12X 109.5 . . ?
N1B C12B H12Y 109.5 . . ?
H12X C12B H12Y 109.5 . . ?
N1B C12B H12Z 109.5 . . ?
H12X C12B H12Z 109.5 . . ?
H12Y C12B H12Z 109.5 . . ?
O1B C13B C9B 119.02(10) . . ?
O1B C13B C14B 119.95(10) . . ?
C9B C13B C14B 119.69(8) . . ?
C17B C14B C15B 111.11(9) . . ?
C17B C14B C13B 113.11(9) . . ?
C15B C14B C13B 109.87(9) . . ?
C17B C14B C16B 109.04(9) . . ?
C15B C14B C16B 108.76(9) . . ?
C13B C14B C16B 104.67(8) . . ?
C14B C15B H15X 109.5 . . ?
C14B C15B H15Y 109.5 . . ?
H15X C15B H15Y 109.5 . . ?
C14B C15B H15Z 109.5 . . ?
H15X C15B H15Z 109.5 . . ?
H15Y C15B H15Z 109.5 . . ?
C14B C16B H16X 109.5 . . ?
C14B C16B H16Y 109.5 . . ?
H16X C16B H16Y 109.5 . . ?
C14B C16B H16Z 109.5 . . ?
H16X C16B H16Z 109.5 . . ?
H16Y C16B H16Z 109.5 . . ?
C14B C17B H17X 109.5 . . ?
C14B C17B H17Y 109.5 . . ?
H17X C17B H17Y 109.5 . . ?
C14B C17B H17Z 109.5 . . ?
H17X C17B H17Z 109.5 . . ?
H17Y C17B H17Z 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 984762'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ketone10

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
8-Benzoyl-1-dimethylaminonaphthalene, 10
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 N O'
_chemical_formula_weight         275.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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                   9.0485(4)
_cell_length_b                   11.9670(5)
_cell_length_c                   14.4409(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.512(5)
_cell_angle_gamma                90.00
_cell_volume                     1491.24(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2645
_cell_measurement_theta_min      2.9047
_cell_measurement_theta_max      28.9496

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3636
_exptl_crystal_size_mid          0.2752
_exptl_crystal_size_min          0.0691
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_min  0.98686
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7562
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         29.00
_reflns_number_total             3429
_reflns_number_gt                2641
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_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)+(0.0391P)²+0.2700P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3429
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1138
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
O1 O 0.91709(13) 0.10109(9) 0.09980(9) 0.0399(3) Uani 1 1 d . . .
N1 N 1.16929(14) 0.24818(11) 0.24316(9) 0.0288(3) Uani 1 1 d . . .
C1 C 1.08873(17) 0.33748(12) 0.27236(11) 0.0261(3) Uani 1 1 d . . .
C2 C 1.1545(2) 0.40676(15) 0.34919(12) 0.0399(4) Uani 1 1 d . . .
H2 H 1.2611 0.3986 0.3845 0.048 Uiso 1 1 calc R . .
C3 C 1.0660(2) 0.48963(15) 0.37624(14) 0.0484(5) Uani 1 1 d . . .
H3 H 1.1137 0.5378 0.4291 0.058 Uiso 1 1 calc R . .
C4 C 0.9135(2) 0.50198(14) 0.32815(13) 0.0432(5) Uani 1 1 d . . .
H4 H 0.8549 0.5574 0.3486 0.052 Uiso 1 1 calc R . .
C5 C 0.84041(19) 0.43305(12) 0.24757(12) 0.0311(4) Uani 1 1 d . . .
C6 C 0.6814(2) 0.44178(15) 0.19756(14) 0.0404(4) Uani 1 1 d . . .
H6 H 0.6202 0.4950 0.2183 0.049 Uiso 1 1 calc R . .
C7 C 0.61388(19) 0.37542(17) 0.12010(13) 0.0436(5) Uani 1 1 d . . .
H7 H 0.5061 0.3819 0.0876 0.052 Uiso 1 1 calc R . .
C8 C 0.70318(18) 0.29730(14) 0.08805(12) 0.0341(4) Uani 1 1 d . . .
H8 H 0.6554 0.2522 0.0330 0.041 Uiso 1 1 calc R . .
C9 C 0.85868(16) 0.28494(12) 0.13492(10) 0.0246(3) Uani 1 1 d . . .
C10 C 0.93029(16) 0.35114(12) 0.21790(10) 0.0237(3) Uani 1 1 d . . .
C11 C 1.1712(2) 0.14613(15) 0.29857(13) 0.0468(5) Uani 1 1 d . . .
H11A H 1.2403 0.1560 0.3648 0.070 Uiso 1 1 calc R . .
H11B H 1.2084 0.0840 0.2674 0.070 Uiso 1 1 calc R . .
H11C H 1.0662 0.1298 0.3007 0.070 Uiso 1 1 calc R . .
C12 C 1.32355(18) 0.27665(17) 0.23733(14) 0.0464(5) Uani 1 1 d . . .
H12A H 1.3182 0.3468 0.2015 0.070 Uiso 1 1 calc R . .
H12B H 1.3606 0.2168 0.2036 0.070 Uiso 1 1 calc R . .
H12C H 1.3952 0.2854 0.3030 0.070 Uiso 1 1 calc R . .
C13 C 0.94504(17) 0.20019(12) 0.09438(10) 0.0259(3) Uani 1 1 d . . .
C14 C 1.04320(16) 0.23907(12) 0.03393(10) 0.0238(3) Uani 1 1 d . . .
C15 C 1.06809(17) 0.35178(13) 0.02009(12) 0.0309(4) Uani 1 1 d . . .
H15 H 1.0222 0.4071 0.0499 0.037 Uiso 1 1 calc R . .
C16 C 1.15948(19) 0.38357(14) -0.03695(13) 0.0387(4) Uani 1 1 d . . .
H16 H 1.1765 0.4606 -0.0460 0.046 Uiso 1 1 calc R . .
C17 C 1.22580(19) 0.30393(15) -0.08063(12) 0.0409(4) Uani 1 1 d . . .
H17 H 1.2880 0.3259 -0.1200 0.049 Uiso 1 1 calc R . .
C18 C 1.20182(19) 0.19229(15) -0.06711(12) 0.0378(4) Uani 1 1 d . . .
H18 H 1.2482 0.1373 -0.0969 0.045 Uiso 1 1 calc R . .
C19 C 1.11059(18) 0.15988(13) -0.01041(11) 0.0304(4) Uani 1 1 d . . .
H19 H 1.0940 0.0827 -0.0018 0.036 Uiso 1 1 calc R . .


_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
O1 C13 1.2200(17) . ?
N1 C1 1.4269(19) . ?
N1 C11 1.457(2) . ?
N1 C12 1.4637(19) . ?
C1 C2 1.369(2) . ?
C1 C10 1.422(2) . ?
C2 C3 1.402(2) . ?
C3 C4 1.353(3) . ?
C4 C5 1.417(2) . ?
C5 C6 1.406(2) . ?
C5 C10 1.420(2) . ?
C6 C7 1.358(3) . ?
C7 C8 1.402(2) . ?
C8 C9 1.374(2) . ?
C9 C10 1.420(2) . ?
C9 C13 1.502(2) . ?
C13 C14 1.495(2) . ?
C14 C19 1.384(2) . ?
C14 C15 1.392(2) . ?
C15 C16 1.385(2) . ?
C16 C17 1.376(2) . ?
C17 C18 1.377(2) . ?
C18 C19 1.382(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
C1 N1 C11 112.84(12) . . ?
C1 N1 C12 115.06(13) . . ?
C12 N1 C11 111.88(14) . . ?
C2 C1 C10 119.91(14) . . ?
C2 C1 N1 123.82(14) . . ?
C10 C1 N1 116.26(12) . . ?
C1 C2 C3 120.54(17) . . ?
C4 C3 C2 120.94(16) . . ?
C3 C4 C5 120.65(16) . . ?
C6 C5 C4 122.08(15) . . ?
C6 C5 C10 119.13(15) . . ?
C4 C5 C10 118.77(15) . . ?
C7 C6 C5 121.12(15) . . ?
C6 C7 C8 120.05(16) . . ?
C9 C8 C7 121.04(16) . . ?
C8 C9 C10 119.70(14) . . ?
C8 C9 C13 117.16(13) . . ?
C10 C9 C13 123.14(13) . . ?
C5 C10 C9 118.85(14) . . ?
C5 C10 C1 119.09(13) . . ?
C9 C10 C1 122.05(13) . . ?
O1 C13 C14 120.74(14) . . ?
O1 C13 C9 119.28(13) . . ?
C14 C13 C9 119.18(12) . . ?
C19 C14 C15 118.98(14) . . ?
C19 C14 C13 118.63(13) . . ?
C15 C14 C13 122.40(13) . . ?
C16 C15 C14 120.21(14) . . ?
C17 C16 C15 120.21(16) . . ?
C16 C17 C18 119.86(15) . . ?
C17 C18 C19 120.27(15) . . ?
C18 C19 C14 120.47(15) . . ?

_diffrn_measured_fraction_theta_max 0.864
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 984763'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ketone11

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
1-dimethylamino-8-trifluoroacetylnaphthalene 11
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 F3 N O'
_chemical_formula_weight         267.25

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'
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   P21/n

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                   12.5626(8)
_cell_length_b                   7.4932(4)
_cell_length_c                   13.1887(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.319(6)
_cell_angle_gamma                90.00
_cell_volume                     1228.44(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1786
_cell_measurement_theta_min      3.1221
_cell_measurement_theta_max      28.8607


_exptl_crystal_description       'thick plate'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2129
_exptl_crystal_size_mid          0.1606
_exptl_crystal_size_min          0.0706
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_min  0.88520
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5369
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0647
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         28.87
_reflns_number_total             2795
_reflns_number_gt                1992
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_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)+(0.0305P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2795
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1017
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
F1 F 0.65761(8) -0.08912(16) 0.38401(8) 0.0381(3) Uani 1 1 d . . .
F2 F 0.50230(8) 0.03038(16) 0.38557(7) 0.0347(3) Uani 1 1 d . . .
F3 F 0.52398(9) -0.25065(17) 0.41332(8) 0.0445(4) Uani 1 1 d . . .
O1 O 0.58105(10) -0.26842(17) 0.20845(10) 0.0316(3) Uani 1 1 d . . .
N1 N 0.57370(11) 0.1328(2) 0.19159(10) 0.0200(3) Uani 1 1 d . . .
C1 C 0.46712(13) 0.1832(2) 0.14476(13) 0.0202(4) Uani 1 1 d . . .
C2 C 0.44197(15) 0.3437(3) 0.09891(14) 0.0274(5) Uani 1 1 d . . .
H2 H 0.4960 0.4324 0.0988 0.033 Uiso 1 1 calc R . .
C3 C 0.33622(15) 0.3783(3) 0.05175(14) 0.0324(5) Uani 1 1 d . . .
H3 H 0.3195 0.4901 0.0194 0.039 Uiso 1 1 calc R . .
C4 C 0.25742(15) 0.2531(3) 0.05204(14) 0.0297(5) Uani 1 1 d . . .
H4 H 0.1864 0.2788 0.0201 0.036 Uiso 1 1 calc R . .
C5 C 0.28035(14) 0.0856(3) 0.09932(13) 0.0226(4) Uani 1 1 d . . .
C6 C 0.20230(14) -0.0496(3) 0.10071(14) 0.0289(5) Uani 1 1 d . . .
H6 H 0.1304 -0.0281 0.0696 0.035 Uiso 1 1 calc R . .
C7 C 0.22822(15) -0.2098(3) 0.14580(15) 0.0333(5) Uani 1 1 d . . .
H7 H 0.1743 -0.2987 0.1459 0.040 Uiso 1 1 calc R . .
C8 C 0.33396(15) -0.2455(3) 0.19226(14) 0.0282(5) Uani 1 1 d . . .
H8 H 0.3514 -0.3585 0.2229 0.034 Uiso 1 1 calc R . .
C9 C 0.41180(13) -0.1177(2) 0.19344(13) 0.0212(4) Uani 1 1 d . . .
C10 C 0.38682(13) 0.0509(2) 0.14689(12) 0.0187(4) Uani 1 1 d . . .
C11 C 0.63878(14) 0.0746(3) 0.11358(14) 0.0287(5) Uani 1 1 d . . .
H11A H 0.6015 -0.0222 0.0729 0.043 Uiso 1 1 calc R . .
H11B H 0.7088 0.0320 0.1473 0.043 Uiso 1 1 calc R . .
H11C H 0.6494 0.1752 0.0686 0.043 Uiso 1 1 calc R . .
C12 C 0.62888(15) 0.2735(3) 0.25688(15) 0.0326(5) Uani 1 1 d . . .
H12A H 0.6443 0.3745 0.2142 0.049 Uiso 1 1 calc R . .
H12B H 0.6964 0.2264 0.2937 0.049 Uiso 1 1 calc R . .
H12C H 0.5827 0.3132 0.3063 0.049 Uiso 1 1 calc R . .
C13 C 0.52314(14) -0.1621(2) 0.24323(13) 0.0218(4) Uani 1 1 d . . .
C14 C 0.55284(14) -0.1139(3) 0.35657(14) 0.0264(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
F1 C14 1.3266(19) . ?
F2 C14 1.337(2) . ?
F3 C14 1.349(2) . ?
O1 C13 1.213(2) . ?
N1 C1 1.441(2) . ?
N1 C12 1.470(2) . ?
N1 C11 1.470(2) . ?
C1 C2 1.363(2) . ?
C1 C10 1.417(2) . ?
C2 C3 1.407(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.364(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.413(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.412(3) . ?
C5 C10 1.417(2) . ?
C6 C7 1.358(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.406(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.367(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.420(2) . ?
C9 C13 1.494(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.531(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
C1 N1 C12 113.17(14) . . ?
C1 N1 C11 110.74(13) . . ?
C12 N1 C11 111.09(15) . . ?
C2 C1 C10 120.40(16) . . ?
C2 C1 N1 124.23(16) . . ?
C10 C1 N1 115.35(16) . . ?
C1 C2 C3 120.15(18) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 120.74(19) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.71(18) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 123.06(17) . . ?
C6 C5 C10 118.42(18) . . ?
C4 C5 C10 118.52(17) . . ?
C7 C6 C5 121.12(18) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 120.69(18) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 120.07(19) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.36(17) . . ?
C8 C9 C13 118.13(17) . . ?
C10 C9 C13 121.51(15) . . ?
C5 C10 C1 119.48(17) . . ?
C5 C10 C9 119.34(16) . . ?
C1 C10 C9 121.15(16) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 C9 123.70(17) . . ?
O1 C13 C14 116.72(16) . . ?
C9 C13 C14 117.19(15) . . ?
F1 C14 F2 107.60(15) . . ?
F1 C14 F3 106.89(14) . . ?
F2 C14 F3 106.17(14) . . ?
F1 C14 C13 113.04(15) . . ?
F2 C14 C13 114.30(15) . . ?
F3 C14 C13 108.37(15) . . ?

_diffrn_measured_fraction_theta_max 0.866
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 984764'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ketone13

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 1-Dimethylamino-4-trifluoroacetylnaphthalene  13
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 F3 N O'
_chemical_formula_weight         267.25

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   7.2319(13)
_cell_length_b                   8.6574(13)
_cell_length_c                   19.901(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1246.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(1)
_cell_measurement_reflns_used    790
_cell_measurement_theta_min      2.9901
_cell_measurement_theta_max      29.0323

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.4483
_exptl_crystal_size_mid          0.2415
_exptl_crystal_size_min          0.0983
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98492
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3862
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         29.10
_reflns_number_total             2549
_reflns_number_gt                1760
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_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. 
 Refined with Friedel opposites merged, (MERG 4, SHELX).
;
_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)+(0.0499P)²+0.0287P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2549
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1298
_refine_ls_wR_factor_gt          0.1140
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
F1 F 0.5454(3) 0.5022(3) 1.25281(9) 0.1213(9) Uani 1 1 d . . .
F2 F 0.7293(3) 0.4803(4) 1.17039(11) 0.1166(10) Uani 1 1 d . . .
F3 F 0.5885(4) 0.6929(3) 1.18868(10) 0.1154(9) Uani 1 1 d . . .
O1 O 0.2961(4) 0.4069(4) 1.17612(11) 0.1045(10) Uani 1 1 d . . .
N7 N 0.4513(4) 0.5858(3) 0.86581(11) 0.0573(7) Uani 1 1 d . . .
C1 C 0.4022(4) 0.5239(3) 1.07475(13) 0.0460(7) Uani 1 1 d . . .
C2 C 0.5443(4) 0.6079(3) 1.04627(13) 0.0502(7) Uani 1 1 d . . .
H2 H 0.6374 0.6485 1.0749 0.060 Uiso 1 1 calc R . .
C3 C 0.5575(4) 0.6358(3) 0.97830(12) 0.0495(7) Uani 1 1 d . . .
H3 H 0.6558 0.6974 0.9615 0.059 Uiso 1 1 calc R . .
C4 C 0.4299(4) 0.5751(3) 0.93468(12) 0.0430(6) Uani 1 1 d . . .
C5 C 0.2658(4) 0.5041(3) 0.96155(13) 0.0419(6) Uani 1 1 d . . .
C6 C 0.1123(4) 0.4707(3) 0.92056(14) 0.0523(7) Uani 1 1 d . . .
H6 H 0.1178 0.4944 0.8740 0.063 Uiso 1 1 calc R . .
C7 C -0.0436(5) 0.4054(4) 0.94597(17) 0.0635(9) Uani 1 1 d . . .
H7 H -0.1446 0.3820 0.9172 0.076 Uiso 1 1 calc R . .
C8 C -0.0546(5) 0.3732(3) 1.01399(17) 0.0626(8) Uani 1 1 d . . .
H8 H -0.1631 0.3263 1.0316 0.075 Uiso 1 1 calc R . .
C9 C 0.0870(4) 0.4075(3) 1.05571(14) 0.0516(7) Uani 1 1 d . . .
H9 H 0.0753 0.3853 1.1023 0.062 Uiso 1 1 calc R . .
C10 C 0.2518(4) 0.4754(3) 1.03181(14) 0.0420(6) Uani 1 1 d . . .
C11 C 0.4411(5) 0.4463(4) 0.82448(15) 0.0704(9) Uani 1 1 d . . .
H15A H 0.3792 0.3641 0.8498 0.106 Uiso 1 1 calc R . .
H15B H 0.5664 0.4129 0.8125 0.106 Uiso 1 1 calc R . .
H15C H 0.3710 0.4683 0.7835 0.106 Uiso 1 1 calc R . .
C12 C 0.5828(5) 0.6972(4) 0.83986(15) 0.0767(10) Uani 1 1 d . . .
H18A H 0.7088 0.6596 0.8475 0.115 Uiso 1 1 calc R . .
H18B H 0.5660 0.7962 0.8629 0.115 Uiso 1 1 calc R . .
H18C H 0.5625 0.7111 0.7915 0.115 Uiso 1 1 calc R . .
C13 C 0.4074(5) 0.4853(4) 1.14599(14) 0.0575(8) Uani 1 1 d . . .
C14 C 0.5706(6) 0.5401(5) 1.18970(15) 0.0756(10) 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
F1 C14 1.311(4) . ?
F2 C14 1.317(4) . ?
F3 C14 1.329(4) . ?
O1 C13 1.211(4) . ?
N7 C4 1.382(3) . ?
N7 C12 1.449(4) . ?
N7 C11 1.464(4) . ?
C1 C2 1.381(4) . ?
C1 C10 1.445(4) . ?
C1 C13 1.457(3) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.371(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.440(4) . ?
C5 C6 1.407(4) . ?
C5 C10 1.424(3) . ?
C6 C7 1.359(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.384(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.351(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.412(4) . ?
C9 H9 0.9500 . ?
C11 H15A 0.9800 . ?
C11 H15B 0.9800 . ?
C11 H15C 0.9800 . ?
C12 H18A 0.9800 . ?
C12 H18B 0.9800 . ?
C12 H18C 0.9800 . ?
C13 C14 1.541(5) . ?

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
C4 N7 C12 118.1(2) . . ?
C4 N7 C11 119.7(2) . . ?
C12 N7 C11 112.5(2) . . ?
C2 C1 C10 118.1(2) . . ?
C2 C1 C13 120.1(3) . . ?
C10 C1 C13 121.9(3) . . ?
C3 C2 C1 123.2(3) . . ?
C3 C2 H2 118.4 . . ?
C1 C2 H2 118.4 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 N7 121.8(3) . . ?
C3 C4 C5 118.9(2) . . ?
N7 C4 C5 119.3(3) . . ?
C6 C5 C10 118.5(3) . . ?
C6 C5 C4 121.5(2) . . ?
C10 C5 C4 119.8(2) . . ?
C7 C6 C5 121.6(3) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C8 119.7(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 121.6(3) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C9 C10 C5 117.6(3) . . ?
C9 C10 C1 123.9(2) . . ?
C5 C10 C1 118.5(2) . . ?
N7 C11 H15A 109.5 . . ?
N7 C11 H15B 109.5 . . ?
H15A C11 H15B 109.5 . . ?
N7 C11 H15C 109.5 . . ?
H15A C11 H15C 109.5 . . ?
H15B C11 H15C 109.5 . . ?
N7 C12 H18A 109.5 . . ?
N7 C12 H18B 109.5 . . ?
H18A C12 H18B 109.5 . . ?
N7 C12 H18C 109.5 . . ?
H18A C12 H18C 109.5 . . ?
H18B C12 H18C 109.5 . . ?
O1 C13 C1 126.4(3) . . ?
O1 C13 C14 113.7(3) . . ?
C1 C13 C14 119.9(3) . . ?
F1 C14 F2 107.6(3) . . ?
F1 C14 F3 106.1(3) . . ?
F2 C14 F3 107.6(3) . . ?
F1 C14 C13 110.9(3) . . ?
F2 C14 C13 112.5(3) . . ?
F3 C14 C13 111.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.855
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.032
_vrf_PLAT242_4ABIP               
; 
PROBLEM: Check Low  Ueq as Compared to Neighbors for C13 and C14          

RESPONSE: This atom forms part of backbone of CF3C=O sidechain. 
The ADPs of F are large due to possible disorder,
 which is quite common for CF3
;
_database_code_depnum_ccdc_archive 'CCDC 984765'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_7Hchloride

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
2-Hydroxy-1,1,2-trimethyl-1,2-dihydrobenzo[cd]indol-1-ium
chloride monohydrate, 7-H.Cl.H2O 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 N O, Cl , H2 O'
_chemical_formula_sum            'C14 H18 Cl N O2'
_chemical_formula_weight         267.74

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   11.3796(3)
_cell_length_b                   10.5436(2)
_cell_length_c                   11.0577(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.604(2)
_cell_angle_gamma                90.00
_cell_volume                     1315.06(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2884
_cell_measurement_theta_min      3.0858
_cell_measurement_theta_max      29.0772

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3410
_exptl_crystal_size_mid          0.2992
_exptl_crystal_size_min          0.2313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            5782
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         29.14
_reflns_number_total             3007
_reflns_number_gt                2500
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_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)+(0.0407P)²+0.6205P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3007
_refine_ls_number_parameters     177
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.0963
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.002

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
Cl1 Cl 0.86131(4) 0.20508(4) 0.84206(4) 0.02338(14) Uani 1 1 d . . .
O1 O 0.11623(12) 0.22806(12) 0.95469(11) 0.0212(3) Uani 1 1 d . . .
O2 O 0.81869(15) 0.09623(14) 0.56434(15) 0.0413(4) Uani 1 1 d D . .
N1 N 0.19107(12) 0.07557(13) 0.81273(12) 0.0150(3) Uani 1 1 d . . .
C1 C 0.31840(14) 0.04871(16) 0.80832(15) 0.0152(3) Uani 1 1 d . . .
C2 C 0.36856(15) -0.05112(16) 0.75723(15) 0.0177(4) Uani 1 1 d . . .
H2 H 0.3221 -0.1142 0.7119 0.021 Uiso 1 1 calc R . .
C3 C 0.49487(16) -0.05608(17) 0.77530(16) 0.0194(4) Uani 1 1 d . . .
H3 H 0.5331 -0.1236 0.7391 0.023 Uiso 1 1 calc R . .
C4 C 0.56354(15) 0.03206(17) 0.84245(16) 0.0197(4) Uani 1 1 d . . .
H4 H 0.6475 0.0249 0.8514 0.024 Uiso 1 1 calc R . .
C5 C 0.51033(15) 0.13412(16) 0.89881(15) 0.0159(4) Uani 1 1 d . . .
C6 C 0.56638(16) 0.23063(17) 0.97428(15) 0.0198(4) Uani 1 1 d . . .
H6 H 0.6503 0.2315 0.9931 0.024 Uiso 1 1 calc R . .
C7 C 0.49993(17) 0.32309(17) 1.02058(16) 0.0216(4) Uani 1 1 d . . .
H7 H 0.5395 0.3858 1.0727 0.026 Uiso 1 1 calc R . .
C8 C 0.37498(16) 0.32883(17) 0.99387(16) 0.0203(4) Uani 1 1 d . . .
H8 H 0.3314 0.3955 1.0249 0.024 Uiso 1 1 calc R . .
C9 C 0.31875(15) 0.23558(16) 0.92209(15) 0.0162(3) Uani 1 1 d . . .
C10 C 0.38589(15) 0.14002(16) 0.87736(15) 0.0155(3) Uani 1 1 d . . .
C11 C 0.14642(16) -0.01443(17) 0.90175(16) 0.0216(4) Uani 1 1 d . . .
H11A H 0.1571 -0.1019 0.8753 0.032 Uiso 1 1 calc R . .
H11B H 0.0621 0.0016 0.9050 0.032 Uiso 1 1 calc R . .
H11C H 0.1910 -0.0016 0.9829 0.032 Uiso 1 1 calc R . .
C12 C 0.11639(15) 0.05860(17) 0.69184(15) 0.0201(4) Uani 1 1 d . . .
H12A H 0.1484 0.1106 0.6304 0.030 Uiso 1 1 calc R . .
H12B H 0.0349 0.0850 0.6982 0.030 Uiso 1 1 calc R . .
H12C H 0.1170 -0.0308 0.6678 0.030 Uiso 1 1 calc R . .
C13 C 0.19054(15) 0.22305(16) 0.86755(15) 0.0164(4) Uani 1 1 d . . .
C14 C 0.15862(17) 0.31487(17) 0.76324(17) 0.0223(4) Uani 1 1 d . . .
H14A H 0.0764 0.3004 0.7269 0.034 Uiso 1 1 calc R . .
H14B H 0.2116 0.3016 0.7014 0.034 Uiso 1 1 calc R . .
H14C H 0.1672 0.4020 0.7939 0.034 Uiso 1 1 calc R . .
H1 H 0.046(2) 0.228(2) 0.919(2) 0.037(7) Uiso 1 1 d . . .
H21 H 0.8282(14) 0.131(2) 0.6342(11) 0.100 Uiso 1 1 d D . .
H22 H 0.838(3) 0.153(2) 0.5167(19) 0.100 Uiso 1 1 d 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. 
The H atoms of the water molecule were constrained to be 0.85 Angstroms from
the  atom and 1.34 Angstroms apart.
;

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
O1 C13 1.364(2) . ?
N1 C1 1.484(2) . ?
N1 C12 1.497(2) . ?
N1 C11 1.503(2) . ?
N1 C13 1.669(2) . ?
C1 C2 1.356(2) . ?
C1 C10 1.394(2) . ?
C2 C3 1.426(2) . ?
C3 C4 1.368(2) . ?
C4 C5 1.419(2) . ?
C5 C10 1.406(2) . ?
C5 C6 1.413(2) . ?
C6 C7 1.374(3) . ?
C7 C8 1.415(3) . ?
C8 C9 1.368(2) . ?
C9 C10 1.394(2) . ?
C9 C13 1.509(2) . ?
C13 C14 1.513(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
C1 N1 C12 112.91(13) . . ?
C1 N1 C11 108.50(13) . . ?
C12 N1 C11 107.94(13) . . ?
C1 N1 C13 103.90(12) . . ?
C12 N1 C13 114.00(12) . . ?
C11 N1 C13 109.42(12) . . ?
C2 C1 C10 122.17(16) . . ?
C2 C1 N1 128.96(15) . . ?
C10 C1 N1 108.65(14) . . ?
C1 C2 C3 116.25(16) . . ?
C4 C3 C2 122.95(16) . . ?
C3 C4 C5 120.48(16) . . ?
C10 C5 C6 115.69(16) . . ?
C10 C5 C4 116.00(15) . . ?
C6 C5 C4 128.31(16) . . ?
C7 C6 C5 120.22(16) . . ?
C6 C7 C8 122.69(16) . . ?
C9 C8 C7 118.06(17) . . ?
C8 C9 C10 119.28(16) . . ?
C8 C9 C13 130.39(16) . . ?
C10 C9 C13 109.95(14) . . ?
C9 C10 C1 113.91(15) . . ?
C9 C10 C5 124.00(16) . . ?
C1 C10 C5 122.09(15) . . ?
O1 C13 C9 111.79(14) . . ?
O1 C13 C14 113.89(15) . . ?
C9 C13 C14 111.75(14) . . ?
O1 C13 N1 108.96(13) . . ?
C9 C13 N1 100.19(12) . . ?
C14 C13 N1 109.35(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 C1 C2 -46.9(2) . . . . ?
C11 N1 C1 C2 72.7(2) . . . . ?
C13 N1 C1 C2 -170.95(17) . . . . ?
C12 N1 C1 C10 138.49(14) . . . . ?
C11 N1 C1 C10 -101.90(15) . . . . ?
C13 N1 C1 C10 14.46(16) . . . . ?
C10 C1 C2 C3 -1.6(3) . . . . ?
N1 C1 C2 C3 -175.51(15) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C10 -2.1(2) . . . . ?
C3 C4 C5 C6 177.61(17) . . . . ?
C10 C5 C6 C7 -0.7(2) . . . . ?
C4 C5 C6 C7 179.58(17) . . . . ?
C5 C6 C7 C8 -1.5(3) . . . . ?
C6 C7 C8 C9 2.2(3) . . . . ?
C7 C8 C9 C10 -0.6(2) . . . . ?
C7 C8 C9 C13 -172.79(17) . . . . ?
C8 C9 C10 C1 178.30(15) . . . . ?
C13 C9 C10 C1 -8.0(2) . . . . ?
C8 C9 C10 C5 -1.6(3) . . . . ?
C13 C9 C10 C5 172.05(15) . . . . ?
C2 C1 C10 C9 179.83(16) . . . . ?
N1 C1 C10 C9 -5.1(2) . . . . ?
C2 C1 C10 C5 -0.2(3) . . . . ?
N1 C1 C10 C5 174.79(14) . . . . ?
C6 C5 C10 C9 2.3(2) . . . . ?
C4 C5 C10 C9 -177.96(15) . . . . ?
C6 C5 C10 C1 -177.67(15) . . . . ?
C4 C5 C10 C1 2.1(2) . . . . ?
C8 C9 C13 O1 -56.3(2) . . . . ?
C10 C9 C13 O1 130.93(15) . . . . ?
C8 C9 C13 C14 72.6(2) . . . . ?
C10 C9 C13 C14 -100.10(16) . . . . ?
C8 C9 C13 N1 -171.63(17) . . . . ?
C10 C9 C13 N1 15.63(16) . . . . ?
C1 N1 C13 O1 -135.24(14) . . . . ?
C12 N1 C13 O1 101.45(16) . . . . ?
C11 N1 C13 O1 -19.52(18) . . . . ?
C1 N1 C13 C9 -17.82(14) . . . . ?
C12 N1 C13 C9 -141.13(14) . . . . ?
C11 N1 C13 C9 97.90(14) . . . . ?
C1 N1 C13 C14 99.71(15) . . . . ?
C12 N1 C13 C14 -23.61(18) . . . . ?
C11 N1 C13 C14 -144.58(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 Cl1 0.84(2) 2.17(3) 3.0114(14) 173(2) 1_455
O2 H21 Cl1 0.85 2.409(3) 3.2540(16) 173(2) .
O2 H22 Cl1 0.85 2.481(6) 3.3137(16) 166(3) 4_565

_diffrn_measured_fraction_theta_max 0.849
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.062
_database_code_depnum_ccdc_archive 'CCDC 984801'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_7Htriflate

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
2-Hydroxy-2-methyl-1,1-dimethyl-1,2-dihydrobenzo[cd]indol-1-ium
triflate at 150K       7-H.triflate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 F3 N O4 S'
_chemical_formula_weight         363.35

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   13.8475(10)
_cell_length_b                   7.7466(4)
_cell_length_c                   15.6785(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.669(6)
_cell_angle_gamma                90.00
_cell_volume                     1611.17(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1894
_cell_measurement_theta_min      2.9629
_cell_measurement_theta_max      28.9149

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.3702
_exptl_crystal_size_mid          0.2388
_exptl_crystal_size_min          0.0524
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            7786
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         28.94
_reflns_number_total             3727
_reflns_number_gt                2988
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_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.

THE TRIFLATE ION IS DISORDERED, LEADING TO EXTRA DIFFERENCE ELECTRON 
DENSITY IN THIS REGION. WE WERE UNABLE TO FIND A SIMPLE SATISFACTORY MODEL
;

_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)+(0.0764P)²+2.3406P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3727
_refine_ls_number_parameters     224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1289
_refine_ls_R_factor_gt           0.1027
_refine_ls_wR_factor_ref         0.2254
_refine_ls_wR_factor_gt          0.2110
_refine_ls_goodness_of_fit_ref   1.235
_refine_ls_restrained_S_all      1.235
_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
S1 S 0.20663(8) 0.89140(14) 0.21615(7) 0.0317(3) Uani 1 1 d . . .
F1 F 0.3668(3) 1.0845(4) 0.2381(3) 0.0699(10) Uani 1 1 d . . .
F2 F 0.3243(2) 0.9427(5) 0.11587(19) 0.0626(9) Uani 1 1 d . . .
F3 F 0.39525(19) 0.8122(4) 0.23821(18) 0.0493(7) Uani 1 1 d . . .
O1 O 0.0934(3) 0.0710(5) 0.3782(2) 0.0521(9) Uani 1 1 d . . .
O2 O 0.1442(2) 1.0287(4) 0.1703(2) 0.0447(8) Uani 1 1 d . . .
O3 O 0.1827(2) 0.7238(4) 0.1787(2) 0.0443(8) Uani 1 1 d . . .
O4 O 0.2265(3) 0.8964(5) 0.3114(2) 0.0476(9) Uani 1 1 d . . .
N1 N 0.1494(2) 0.3757(5) 0.3772(2) 0.0330(8) Uani 1 1 d . . .
C1 C 0.2579(3) 0.3645(5) 0.3850(3) 0.0301(9) Uani 1 1 d . . .
C2 C 0.3114(3) 0.4514(6) 0.3375(3) 0.0344(9) Uani 1 1 d . . .
H2 H 0.2795 0.5241 0.2888 0.041 Uiso 1 1 calc R . .
C3 C 0.4167(3) 0.4268(6) 0.3652(3) 0.0377(10) Uani 1 1 d . . .
H3 H 0.4562 0.4830 0.3329 0.045 Uiso 1 1 calc R . .
C4 C 0.4646(3) 0.3265(6) 0.4360(3) 0.0355(10) Uani 1 1 d . . .
H4 H 0.5359 0.3156 0.4523 0.043 Uiso 1 1 calc R . .
C5 C 0.4092(3) 0.2383(5) 0.4855(3) 0.0304(9) Uani 1 1 d . . .
C6 C 0.4454(4) 0.1314(6) 0.5604(3) 0.0392(11) Uani 1 1 d . . .
H6 H 0.5158 0.1125 0.5844 0.047 Uiso 1 1 calc R . .
C7 C 0.3791(4) 0.0546(6) 0.5988(3) 0.0462(12) Uani 1 1 d . . .
H7 H 0.4056 -0.0151 0.6501 0.055 Uiso 1 1 calc R . .
C8 C 0.2746(4) 0.0734(6) 0.5663(3) 0.0456(12) Uani 1 1 d . . .
H8 H 0.2308 0.0161 0.5939 0.055 Uiso 1 1 calc R . .
C9 C 0.2374(3) 0.1764(6) 0.4938(3) 0.0361(10) Uani 1 1 d . . .
C10 C 0.3044(3) 0.2593(5) 0.4563(3) 0.0279(8) Uani 1 1 d . . .
C11 C 0.0848(3) 0.3650(7) 0.2833(3) 0.0438(11) Uani 1 1 d . . .
H11A H 0.0954 0.4679 0.2507 0.066 Uiso 1 1 calc R . .
H11B H 0.0138 0.3585 0.2823 0.066 Uiso 1 1 calc R . .
H11C H 0.1027 0.2618 0.2550 0.066 Uiso 1 1 calc R . .
C12 C 0.1293(4) 0.5474(6) 0.4145(3) 0.0439(11) Uani 1 1 d . . .
H12A H 0.1686 0.5554 0.4772 0.066 Uiso 1 1 calc R . .
H12B H 0.0573 0.5571 0.4096 0.066 Uiso 1 1 calc R . .
H12C H 0.1489 0.6410 0.3808 0.066 Uiso 1 1 calc R . .
C13 C 0.1304(3) 0.2088(6) 0.4379(3) 0.0417(11) Uani 1 1 d . . .
C14 C 0.0562(4) 0.2552(8) 0.4859(3) 0.0558(15) Uani 1 1 d . . .
H14A H -0.0076 0.2887 0.4428 0.084 Uiso 1 1 calc R . .
H14B H 0.0821 0.3519 0.5262 0.084 Uiso 1 1 calc R . .
H14C H 0.0448 0.1556 0.5203 0.084 Uiso 1 1 calc R . .
C20 C 0.3303(3) 0.9371(6) 0.2027(3) 0.0400(11) Uani 1 1 d . . .
H1 H 0.147(6) 0.010(10) 0.366(5) 0.11(3) Uiso 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
S1 O3 1.424(3) . ?
S1 O2 1.427(3) . ?
S1 O4 1.440(3) . ?
S1 C20 1.820(5) . ?
F1 C20 1.307(6) . ?
F2 C20 1.340(5) . ?
F3 C20 1.329(5) . ?
O1 C13 1.415(6) . ?
N1 C1 1.474(5) . ?
N1 C11 1.490(5) . ?
N1 C12 1.511(6) . ?
N1 C13 1.670(6) . ?
C1 C2 1.369(6) . ?
C1 C10 1.384(6) . ?
C2 C3 1.411(6) . ?
C3 C4 1.362(6) . ?
C4 C5 1.414(6) . ?
C5 C10 1.400(6) . ?
C5 C6 1.407(6) . ?
C6 C7 1.369(7) . ?
C7 C8 1.398(7) . ?
C8 C9 1.363(6) . ?
C9 C10 1.391(6) . ?
C9 C13 1.511(6) . ?
C13 C14 1.482(6) . ?

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
O3 S1 O2 115.8(2) . . ?
O3 S1 O4 113.9(2) . . ?
O2 S1 O4 114.2(2) . . ?
O3 S1 C20 104.2(2) . . ?
O2 S1 C20 104.5(2) . . ?
O4 S1 C20 102.1(2) . . ?
C1 N1 C11 112.8(3) . . ?
C1 N1 C12 108.4(3) . . ?
C11 N1 C12 107.8(4) . . ?
C1 N1 C13 103.3(3) . . ?
C11 N1 C13 111.9(3) . . ?
C12 N1 C13 112.6(3) . . ?
C2 C1 C10 121.9(4) . . ?
C2 C1 N1 128.6(4) . . ?
C10 C1 N1 109.3(3) . . ?
C1 C2 C3 116.1(4) . . ?
C4 C3 C2 123.2(4) . . ?
C3 C4 C5 120.6(4) . . ?
C10 C5 C6 115.4(4) . . ?
C10 C5 C4 116.0(4) . . ?
C6 C5 C4 128.6(4) . . ?
C7 C6 C5 120.0(4) . . ?
C6 C7 C8 123.3(4) . . ?
C9 C8 C7 117.9(4) . . ?
C8 C9 C10 119.0(4) . . ?
C8 C9 C13 130.9(4) . . ?
C10 C9 C13 109.9(4) . . ?
C1 C10 C9 113.6(4) . . ?
C1 C10 C5 122.1(4) . . ?
C9 C10 C5 124.2(4) . . ?
O1 C13 C14 110.3(4) . . ?
O1 C13 C9 111.6(4) . . ?
C14 C13 C9 116.9(4) . . ?
O1 C13 N1 107.1(3) . . ?
C14 C13 N1 110.3(4) . . ?
C9 C13 N1 99.8(3) . . ?
F1 C20 F3 109.0(4) . . ?
F1 C20 F2 107.9(4) . . ?
F3 C20 F2 106.7(4) . . ?
F1 C20 S1 112.5(3) . . ?
F3 C20 S1 110.8(3) . . ?
F2 C20 S1 109.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C1 C2 47.4(6) . . . . ?
C12 N1 C1 C2 -71.9(5) . . . . ?
C13 N1 C1 C2 168.4(4) . . . . ?
C11 N1 C1 C10 -138.0(4) . . . . ?
C12 N1 C1 C10 102.7(4) . . . . ?
C13 N1 C1 C10 -17.0(4) . . . . ?
C10 C1 C2 C3 0.3(6) . . . . ?
N1 C1 C2 C3 174.3(4) . . . . ?
C1 C2 C3 C4 -1.5(7) . . . . ?
C2 C3 C4 C5 0.9(7) . . . . ?
C3 C4 C5 C10 0.9(6) . . . . ?
C3 C4 C5 C6 -179.3(4) . . . . ?
C10 C5 C6 C7 0.8(6) . . . . ?
C4 C5 C6 C7 -179.0(4) . . . . ?
C5 C6 C7 C8 1.3(8) . . . . ?
C6 C7 C8 C9 -1.3(8) . . . . ?
C7 C8 C9 C10 -0.8(7) . . . . ?
C7 C8 C9 C13 173.0(5) . . . . ?
C2 C1 C10 C9 -177.5(4) . . . . ?
N1 C1 C10 C9 7.5(5) . . . . ?
C2 C1 C10 C5 1.5(6) . . . . ?
N1 C1 C10 C5 -173.5(4) . . . . ?
C8 C9 C10 C1 -178.0(4) . . . . ?
C13 C9 C10 C1 7.0(5) . . . . ?
C8 C9 C10 C5 3.1(7) . . . . ?
C13 C9 C10 C5 -171.9(4) . . . . ?
C6 C5 C10 C1 178.1(4) . . . . ?
C4 C5 C10 C1 -2.1(6) . . . . ?
C6 C5 C10 C9 -3.0(6) . . . . ?
C4 C5 C10 C9 176.8(4) . . . . ?
C8 C9 C13 O1 -77.5(6) . . . . ?
C10 C9 C13 O1 96.7(4) . . . . ?
C8 C9 C13 C14 50.7(7) . . . . ?
C10 C9 C13 C14 -135.1(5) . . . . ?
C8 C9 C13 N1 169.6(5) . . . . ?
C10 C9 C13 N1 -16.2(4) . . . . ?
C1 N1 C13 O1 -96.8(4) . . . . ?
C11 N1 C13 O1 24.8(5) . . . . ?
C12 N1 C13 O1 146.5(4) . . . . ?
C1 N1 C13 C14 143.2(4) . . . . ?
C11 N1 C13 C14 -95.2(5) . . . . ?
C12 N1 C13 C14 26.5(5) . . . . ?
C1 N1 C13 C9 19.5(4) . . . . ?
C11 N1 C13 C9 141.1(4) . . . . ?
C12 N1 C13 C9 -97.2(4) . . . . ?
O3 S1 C20 F1 -176.6(3) . . . . ?
O2 S1 C20 F1 61.4(4) . . . . ?
O4 S1 C20 F1 -57.9(4) . . . . ?
O3 S1 C20 F3 -54.4(4) . . . . ?
O2 S1 C20 F3 -176.4(3) . . . . ?
O4 S1 C20 F3 64.4(4) . . . . ?
O3 S1 C20 F2 63.2(4) . . . . ?
O2 S1 C20 F2 -58.8(4) . . . . ?
O4 S1 C20 F2 -178.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.876
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.779
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.084

_vrf_RFACG01_mejabs              
; 
PROBLEM: The value of the R factor is > 0.10
            R factor given   0.103     

RESPONSE: there is unresolved disorder in the triflate ion
;
_database_code_depnum_ccdc_archive 'CCDC 984802'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_8HBF4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
2-Hydroxy-2-isopropyl-1,1-dimethyl-1,2-dihydrobenzo[cd]indol-1-ium
tetrafluoroborate, 8-H.BF4
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H20 B F4 N O'
_chemical_formula_weight         329.14

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'
B B 0.0013 0.0007 '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   P21/n

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                   6.2039(2)
_cell_length_b                   10.6675(3)
_cell_length_c                   23.5777(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.541(3)
_cell_angle_gamma                90.00
_cell_volume                     1546.88(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2237
_cell_measurement_theta_min      3.2313
_cell_measurement_theta_max      29.0798

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.4234
_exptl_crystal_size_mid          0.1046
_exptl_crystal_size_min          0.0584
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_min  0.95377
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7127
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.24
_diffrn_reflns_theta_max         29.14
_reflns_number_total             3555
_reflns_number_gt                2809
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_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)+(0.0597P)²+1.0194P] 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         3555
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.1424
_refine_ls_wR_factor_gt          0.1321
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
F1 F 0.2022(3) 0.61308(15) 0.03384(6) 0.0588(5) Uani 1 1 d . . .
F2 F -0.0780(3) 0.69032(18) 0.07266(7) 0.0540(5) Uani 1 1 d . . .
F3 F 0.1254(3) 0.81774(12) 0.02479(5) 0.0359(4) Uani 1 1 d . . .
F4 F 0.2594(3) 0.73745(18) 0.11166(7) 0.0597(5) Uani 1 1 d . . .
O1 O 0.8699(2) 0.24063(14) 0.08581(6) 0.0183(3) Uani 1 1 d . . .
N1 N 0.5193(2) 0.33825(15) 0.09730(6) 0.0142(3) Uani 1 1 d . . .
C1 C 0.4201(3) 0.34937(18) 0.15077(8) 0.0156(4) Uani 1 1 d . . .
C2 C 0.2492(3) 0.42010(19) 0.16208(9) 0.0199(4) Uani 1 1 d . . .
H2 H 0.1622 0.4657 0.1330 0.024 Uiso 1 1 calc R . .
C3 C 0.2075(3) 0.4223(2) 0.21991(9) 0.0243(5) Uani 1 1 d . . .
H3 H 0.0854 0.4681 0.2291 0.029 Uiso 1 1 calc R . .
C4 C 0.3352(3) 0.3614(2) 0.26295(9) 0.0240(5) Uani 1 1 d . . .
H4 H 0.3010 0.3662 0.3010 0.029 Uiso 1 1 calc R . .
C5 C 0.5187(3) 0.2910(2) 0.25125(8) 0.0208(4) Uani 1 1 d . . .
C6 C 0.6748(4) 0.2279(2) 0.29044(9) 0.0260(5) Uani 1 1 d . . .
H6 H 0.6617 0.2281 0.3301 0.031 Uiso 1 1 calc R . .
C7 C 0.8449(4) 0.1664(2) 0.27084(9) 0.0264(5) Uani 1 1 d . . .
H7 H 0.9503 0.1269 0.2979 0.032 Uiso 1 1 calc R . .
C8 C 0.8705(3) 0.1592(2) 0.21212(8) 0.0221(4) Uani 1 1 d . . .
H8 H 0.9888 0.1148 0.1999 0.027 Uiso 1 1 calc R . .
C9 C 0.7198(3) 0.21793(18) 0.17362(8) 0.0161(4) Uani 1 1 d . . .
C10 C 0.5520(3) 0.28499(18) 0.19360(8) 0.0164(4) Uani 1 1 d . . .
C11 C 0.3596(3) 0.3295(2) 0.04404(8) 0.0192(4) Uani 1 1 d . . .
H11A H 0.2618 0.2585 0.0471 0.029 Uiso 1 1 calc R . .
H11B H 0.4379 0.3173 0.0110 0.029 Uiso 1 1 calc R . .
H11C H 0.2746 0.4071 0.0391 0.029 Uiso 1 1 calc R . .
C12 C 0.6554(3) 0.45404(19) 0.09302(8) 0.0186(4) Uani 1 1 d . . .
H12A H 0.5616 0.5283 0.0903 0.028 Uiso 1 1 calc R . .
H12B H 0.7295 0.4485 0.0589 0.028 Uiso 1 1 calc R . .
H12C H 0.7637 0.4606 0.1271 0.028 Uiso 1 1 calc R . .
C13 C 0.6840(3) 0.21545(18) 0.10909(8) 0.0148(4) Uani 1 1 d . . .
C14 C 0.5675(3) 0.09570(19) 0.08471(8) 0.0186(4) Uani 1 1 d . . .
H14 H 0.5146 0.1109 0.0434 0.022 Uiso 1 1 calc R . .
C15 C 0.3717(3) 0.0580(2) 0.11429(9) 0.0251(5) Uani 1 1 d . . .
H15A H 0.2946 -0.0115 0.0934 0.038 Uiso 1 1 calc R . .
H15B H 0.2733 0.1298 0.1148 0.038 Uiso 1 1 calc R . .
H15C H 0.4219 0.0318 0.1536 0.038 Uiso 1 1 calc R . .
C16 C 0.7291(4) -0.0128(2) 0.08840(10) 0.0299(5) Uani 1 1 d . . .
H16A H 0.7944 -0.0240 0.1282 0.045 Uiso 1 1 calc R . .
H16B H 0.8434 0.0058 0.0646 0.045 Uiso 1 1 calc R . .
H16C H 0.6533 -0.0898 0.0747 0.045 Uiso 1 1 calc R . .
B1 B 0.1304(4) 0.7143(2) 0.06174(9) 0.0213(5) Uani 1 1 d . . .
H1 H 0.854(4) 0.217(3) 0.0498(12) 0.039(8) Uiso 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
F1 B1 1.369(3) . ?
F2 B1 1.375(3) . ?
F3 B1 1.404(3) . ?
F4 B1 1.356(3) . ?
O1 C13 1.367(2) . ?
O1 H1 0.88(3) . ?
N1 C1 1.478(2) . ?
N1 C11 1.497(2) . ?
N1 C12 1.507(2) . ?
N1 C13 1.662(2) . ?
C1 C2 1.356(3) . ?
C1 C10 1.394(3) . ?
C2 C3 1.421(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.367(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.421(3) . ?
C4 H4 0.9500 . ?
C5 C10 1.403(3) . ?
C5 C6 1.417(3) . ?
C6 C7 1.373(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.416(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.367(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.395(3) . ?
C9 C13 1.509(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.541(3) . ?
C14 C16 1.526(3) . ?
C14 C15 1.532(3) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C13 O1 H1 109.7(18) . . ?
C1 N1 C11 114.64(14) . . ?
C1 N1 C12 106.92(14) . . ?
C11 N1 C12 108.03(15) . . ?
C1 N1 C13 103.66(13) . . ?
C11 N1 C13 114.59(14) . . ?
C12 N1 C13 108.63(13) . . ?
C2 C1 C10 122.10(18) . . ?
C2 C1 N1 129.49(17) . . ?
C10 C1 N1 107.92(16) . . ?
C1 C2 C3 116.32(19) . . ?
C1 C2 H2 121.8 . . ?
C3 C2 H2 121.8 . . ?
C4 C3 C2 122.94(19) . . ?
C4 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
C3 C4 C5 120.55(18) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C10 C5 C6 115.79(19) . . ?
C10 C5 C4 115.83(18) . . ?
C6 C5 C4 128.37(19) . . ?
C7 C6 C5 119.80(19) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 122.99(19) . . ?
C6 C7 H7 118.5 . . ?
C8 C7 H7 118.5 . . ?
C9 C8 C7 118.03(19) . . ?
C9 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
C8 C9 C10 119.11(18) . . ?
C8 C9 C13 131.24(18) . . ?
C10 C9 C13 109.38(16) . . ?
C1 C10 C9 113.65(17) . . ?
C1 C10 C5 122.16(18) . . ?
C9 C10 C5 124.18(18) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 C9 112.39(15) . . ?
O1 C13 C14 113.06(16) . . ?
C9 C13 C14 112.99(16) . . ?
O1 C13 N1 108.09(14) . . ?
C9 C13 N1 99.26(14) . . ?
C14 C13 N1 110.07(14) . . ?
C16 C14 C15 109.24(17) . . ?
C16 C14 C13 109.58(16) . . ?
C15 C14 C13 114.11(16) . . ?
C16 C14 H14 107.9 . . ?
C15 C14 H14 107.9 . . ?
C13 C14 H14 107.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F4 B1 F1 111.6(2) . . ?
F4 B1 F2 109.50(19) . . ?
F1 B1 F2 108.5(2) . . ?
F4 B1 F3 110.96(19) . . ?
F1 B1 F3 107.69(17) . . ?
F2 B1 F3 108.53(19) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 F3 0.88(3) 1.82(3) 2.6851(19) 168(3) 3_665

_diffrn_measured_fraction_theta_max 0.850
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 984803'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_9Htriflate

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
1-dimethylammonium-8-(2,2-dimethylpropanoyl)naphthalene
triflate 9-H.triflate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 F3 N O4 S'
_chemical_formula_weight         405.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   21.072(4)
_cell_length_b                   11.828(3)
_cell_length_c                   16.397(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.765(14)
_cell_angle_gamma                90.00
_cell_volume                     3768.5(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13586
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      31.3


_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9607
_exptl_absorpt_correction_T_max  0.9779
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011) 
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Mitegen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25396
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         27.50
_reflns_number_total             8602
_reflns_number_gt                7821
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011) 
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_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. 
Refined as a twin: 
TWIN    1.00  0.00  1.00  0.00 -1.00  0.00  0.00  0.00 -1.00   2
BASF 0.47
;

_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)+(0.0420P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8602
_refine_ls_number_parameters     506
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.0882
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
O1A O 0.41672(8) 0.64178(12) 0.24414(9) 0.0203(3) Uani 1 1 d . . .
N1A N 0.34772(9) 0.67971(14) 0.07378(12) 0.0177(4) Uani 1 1 d . . .
C1A C 0.40656(11) 0.67605(16) 0.04525(13) 0.0166(4) Uani 1 1 d . . .
C2A C 0.39581(12) 0.72393(18) -0.03433(14) 0.0213(5) Uani 1 1 d . . .
H2A H 0.3523 0.7567 -0.0679 0.026 Uiso 1 1 calc R . .
C3A C 0.44792(12) 0.72579(19) -0.06778(15) 0.0234(5) Uani 1 1 d . . .
H3A H 0.4397 0.7584 -0.1239 0.028 Uiso 1 1 calc R . .
C4A C 0.51056(12) 0.68013(17) -0.01848(14) 0.0226(5) Uani 1 1 d . . .
H4A H 0.5467 0.6845 -0.0393 0.027 Uiso 1 1 calc R . .
C5A C 0.52237(11) 0.62661(16) 0.06298(14) 0.0176(4) Uani 1 1 d . . .
C6A C 0.58816(11) 0.57752(17) 0.10917(15) 0.0222(5) Uani 1 1 d . . .
H6A H 0.6230 0.5865 0.0864 0.027 Uiso 1 1 calc R . .
C7A C 0.60238(11) 0.51821(17) 0.18483(15) 0.0223(5) Uani 1 1 d . . .
H7A H 0.6464 0.4849 0.2147 0.027 Uiso 1 1 calc R . .
C8A C 0.55060(11) 0.50725(17) 0.21781(15) 0.0200(5) Uani 1 1 d . . .
H8A H 0.5601 0.4630 0.2696 0.024 Uiso 1 1 calc R . .
C9A C 0.48686(11) 0.55665(16) 0.17982(13) 0.0145(4) Uani 1 1 d . . .
C10A C 0.46987(10) 0.62063(15) 0.09842(13) 0.0165(4) Uani 1 1 d . . .
C11A C 0.30126(13) 0.7805(2) 0.04242(16) 0.0323(6) Uani 1 1 d . . .
H11A H 0.3291 0.8494 0.0530 0.048 Uiso 1 1 calc R . .
H11B H 0.2708 0.7849 0.0748 0.048 Uiso 1 1 calc R . .
H11C H 0.2735 0.7730 -0.0210 0.048 Uiso 1 1 calc R . .
C12A C 0.30661(12) 0.57248(19) 0.05027(15) 0.0275(5) Uani 1 1 d . . .
H12A H 0.2842 0.5659 -0.0142 0.041 Uiso 1 1 calc R . .
H12B H 0.2715 0.5738 0.0757 0.041 Uiso 1 1 calc R . .
H12C H 0.3372 0.5077 0.0739 0.041 Uiso 1 1 calc R . .
C13A C 0.44507(11) 0.55453(17) 0.23597(13) 0.0168(4) Uani 1 1 d . . .
C14A C 0.43837(11) 0.44852(18) 0.28617(14) 0.0195(5) Uani 1 1 d . . .
C15A C 0.36676(12) 0.4532(2) 0.29065(17) 0.0287(5) Uani 1 1 d . . .
H15A H 0.3619 0.5243 0.3183 0.043 Uiso 1 1 calc R . .
H15B H 0.3616 0.3894 0.3258 0.043 Uiso 1 1 calc R . .
H15C H 0.3312 0.4488 0.2307 0.043 Uiso 1 1 calc R . .
C16A C 0.44332(12) 0.33772(17) 0.24036(14) 0.0230(5) Uani 1 1 d . . .
H16A H 0.4136 0.3422 0.1774 0.034 Uiso 1 1 calc R . .
H16B H 0.4285 0.2747 0.2675 0.034 Uiso 1 1 calc R . .
H16C H 0.4910 0.3255 0.2469 0.034 Uiso 1 1 calc R . .
C17A C 0.49238(12) 0.45406(19) 0.38277(14) 0.0254(5) Uani 1 1 d . . .
H17A H 0.5388 0.4488 0.3827 0.038 Uiso 1 1 calc R . .
H17B H 0.4849 0.3911 0.4169 0.038 Uiso 1 1 calc R . .
H17C H 0.4876 0.5258 0.4097 0.038 Uiso 1 1 calc R . .
H1A H 0.3692(12) 0.6844(18) 0.1336(16) 0.025(7) Uiso 1 1 d . . .
O1B O 0.92723(8) 0.85971(11) 0.17775(9) 0.0186(3) Uani 1 1 d . . .
N1B N 0.85157(9) 0.83209(14) 0.27371(12) 0.0176(4) Uani 1 1 d . . .
C1B C 0.91088(11) 0.82933(16) 0.36116(13) 0.0167(4) Uani 1 1 d . . .
C2B C 0.90028(12) 0.77631(18) 0.42897(14) 0.0220(5) Uani 1 1 d . . .
H2B H 0.8570 0.7423 0.4183 0.026 Uiso 1 1 calc R . .
C3B C 0.95250(13) 0.77143(18) 0.51421(15) 0.0235(5) Uani 1 1 d . . .
H3B H 0.9445 0.7345 0.5608 0.028 Uiso 1 1 calc R . .
C4B C 1.01430(13) 0.81985(18) 0.52935(14) 0.0227(5) Uani 1 1 d . . .
H4B H 1.0501 0.8143 0.5864 0.027 Uiso 1 1 calc R . .
C5B C 1.02635(11) 0.87854(16) 0.46144(14) 0.0189(5) Uani 1 1 d . . .
C6B C 1.09128(11) 0.93124(17) 0.48306(15) 0.0223(5) Uani 1 1 d . . .
H6B H 1.1259 0.9216 0.5406 0.027 Uiso 1 1 calc R . .
C7B C 1.10474(11) 0.99550(17) 0.42273(14) 0.0228(5) Uani 1 1 d . . .
H7B H 1.1479 1.0324 0.4381 0.027 Uiso 1 1 calc R . .
C8B C 1.05356(11) 1.00618(17) 0.33722(14) 0.0195(5) Uani 1 1 d . . .
H8B H 1.0626 1.0529 0.2959 0.023 Uiso 1 1 calc R . .
C9B C 0.99120(11) 0.95249(16) 0.31063(13) 0.0162(4) Uani 1 1 d . . .
C10B C 0.97424(10) 0.88573(16) 0.37386(13) 0.0157(4) Uani 1 1 d . . .
C11B C 0.80080(12) 0.73698(19) 0.25704(16) 0.0268(5) Uani 1 1 d . . .
H11Y H 0.8255 0.6649 0.2718 0.040 Uiso 1 1 calc R . .
H11Z H 0.7697 0.7368 0.1945 0.040 Uiso 1 1 calc R . .
H11X H 0.7741 0.7472 0.2939 0.040 Uiso 1 1 calc R . .
C12B C 0.81487(11) 0.94335(18) 0.25976(15) 0.0233(5) Uani 1 1 d . . .
H12X H 0.7919 0.9504 0.3013 0.035 Uiso 1 1 calc R . .
H12Y H 0.7806 0.9475 0.1990 0.035 Uiso 1 1 calc R . .
H12Z H 0.8482 1.0049 0.2699 0.035 Uiso 1 1 calc R . .
C13B C 0.95089(10) 0.95111(16) 0.21233(13) 0.0152(4) Uani 1 1 d . . .
C14B C 0.94111(11) 1.05536(17) 0.15326(14) 0.0193(5) Uani 1 1 d . . .
C15B C 0.87010(12) 1.04417(19) 0.07599(15) 0.0276(5) Uani 1 1 d . . .
H15X H 0.8672 0.9710 0.0467 0.041 Uiso 1 1 calc R . .
H15Y H 0.8645 1.1052 0.0333 0.041 Uiso 1 1 calc R . .
H15Z H 0.8336 1.0492 0.0990 0.041 Uiso 1 1 calc R . .
C16B C 0.94165(12) 1.16650(16) 0.20101(15) 0.0240(5) Uani 1 1 d . . .
H16Z H 0.9102 1.1608 0.2319 0.036 Uiso 1 1 calc R . .
H16X H 0.9267 1.2282 0.1578 0.036 Uiso 1 1 calc R . .
H16Y H 0.9884 1.1818 0.2439 0.036 Uiso 1 1 calc R . .
C17B C 0.99630(12) 1.05445(19) 0.11309(15) 0.0268(5) Uani 1 1 d . . .
H17Z H 1.0419 1.0653 0.1602 0.040 Uiso 1 1 calc R . .
H17X H 0.9871 1.1157 0.0698 0.040 Uiso 1 1 calc R . .
H17Y H 0.9950 0.9818 0.0838 0.040 Uiso 1 1 calc R . .
H1B H 0.8711(12) 0.8261(18) 0.2320(15) 0.024(6) Uiso 1 1 d . . .
S1C S 0.26429(3) 0.26486(4) 0.00818(4) 0.01957(13) Uani 1 1 d . . .
F1C F 0.27127(9) 0.06663(12) 0.08324(10) 0.0516(5) Uani 1 1 d . . .
F2C F 0.30408(9) 0.06665(12) -0.02556(10) 0.0445(4) Uani 1 1 d . . .
F3C F 0.36977(8) 0.13666(12) 0.09986(11) 0.0468(4) Uani 1 1 d . . .
O1C O 0.31108(9) 0.31990(12) -0.02325(11) 0.0319(4) Uani 1 1 d . . .
O2C O 0.26232(9) 0.31259(13) 0.08819(10) 0.0284(4) Uani 1 1 d . . .
O3C O 0.19849(8) 0.23714(14) -0.05900(11) 0.0286(4) Uani 1 1 d . . .
C1C C 0.30437(13) 0.12773(19) 0.04314(15) 0.0306(6) Uani 1 1 d . . .
S1D S 0.23701(3) 0.75035(5) 0.23873(4) 0.01912(12) Uani 1 1 d . . .
F1D F 0.12342(8) 0.86047(12) 0.21867(11) 0.0450(4) Uani 1 1 d . . .
F2D F 0.21674(10) 0.94597(12) 0.29949(11) 0.0495(4) Uani 1 1 d . . .
F3D F 0.18544(8) 0.94127(12) 0.15864(11) 0.0433(4) Uani 1 1 d . . .
O1D O 0.30241(8) 0.79048(13) 0.24254(11) 0.0281(4) Uani 1 1 d . . .
O2D O 0.19717(9) 0.68996(13) 0.15931(11) 0.0315(4) Uani 1 1 d . . .
O3D O 0.23701(8) 0.70057(13) 0.31856(10) 0.0264(4) Uani 1 1 d . . .
C1D C 0.18829(12) 0.88032(19) 0.22859(16) 0.0280(5) 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
O1A C13A 1.226(2) . ?
N1A C1A 1.485(3) . ?
N1A C12A 1.500(3) . ?
N1A C11A 1.502(3) . ?
N1A H1A 0.91(2) . ?
C1A C2A 1.359(3) . ?
C1A C10A 1.439(3) . ?
C2A C3A 1.405(3) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.364(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.411(3) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.421(3) . ?
C5A C10A 1.437(3) . ?
C6A C7A 1.354(3) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.399(3) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.373(3) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.453(3) . ?
C9A C13A 1.501(3) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C13A C14A 1.536(3) . ?
C14A C16A 1.534(3) . ?
C14A C15A 1.540(3) . ?
C14A C17A 1.553(3) . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
O1B C13B 1.233(2) . ?
N1B C1B 1.494(3) . ?
N1B C12B 1.498(3) . ?
N1B C11B 1.503(3) . ?
N1B H1B 0.93(2) . ?
C1B C2B 1.368(3) . ?
C1B C10B 1.434(3) . ?
C2B C3B 1.406(3) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.355(3) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.416(3) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.418(3) . ?
C5B C10B 1.434(3) . ?
C6B C7B 1.362(3) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.405(3) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.370(3) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.454(3) . ?
C9B C13B 1.503(3) . ?
C11B H11Y 0.9800 . ?
C11B H11Z 0.9800 . ?
C11B H11X 0.9800 . ?
C12B H12X 0.9800 . ?
C12B H12Y 0.9800 . ?
C12B H12Z 0.9800 . ?
C13B C14B 1.532(3) . ?
C14B C16B 1.528(3) . ?
C14B C17B 1.543(3) . ?
C14B C15B 1.548(3) . ?
C15B H15X 0.9800 . ?
C15B H15Y 0.9800 . ?
C15B H15Z 0.9800 . ?
C16B H16Z 0.9800 . ?
C16B H16X 0.9800 . ?
C16B H16Y 0.9800 . ?
C17B H17Z 0.9800 . ?
C17B H17X 0.9800 . ?
C17B H17Y 0.9800 . ?
S1C O1C 1.4335(16) . ?
S1C O3C 1.4358(16) . ?
S1C O2C 1.4435(16) . ?
S1C C1C 1.816(2) . ?
F1C C1C 1.340(3) . ?
F2C C1C 1.336(3) . ?
F3C C1C 1.335(3) . ?
S1D O3D 1.4352(16) . ?
S1D O1D 1.4360(16) . ?
S1D O2D 1.4369(16) . ?
S1D C1D 1.820(2) . ?
F1D C1D 1.333(3) . ?
F2D C1D 1.332(3) . ?
F3D C1D 1.336(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
C1A N1A C12A 111.35(16) . . ?
C1A N1A C11A 115.37(16) . . ?
C12A N1A C11A 110.37(19) . . ?
C1A N1A H1A 102.4(15) . . ?
C12A N1A H1A 109.0(14) . . ?
C11A N1A H1A 107.9(14) . . ?
C2A C1A C10A 122.9(2) . . ?
C2A C1A N1A 116.17(19) . . ?
C10A C1A N1A 120.92(17) . . ?
C1A C2A C3A 121.1(2) . . ?
C1A C2A H2A 119.4 . . ?
C3A C2A H2A 119.4 . . ?
C4A C3A C2A 119.1(2) . . ?
C4A C3A H3A 120.5 . . ?
C2A C3A H3A 120.5 . . ?
C3A C4A C5A 121.0(2) . . ?
C3A C4A H4A 119.5 . . ?
C5A C4A H4A 119.5 . . ?
C4A C5A C6A 117.8(2) . . ?
C4A C5A C10A 121.6(2) . . ?
C6A C5A C10A 120.62(19) . . ?
C7A C6A C5A 121.6(2) . . ?
C7A C6A H6A 119.2 . . ?
C5A C6A H6A 119.2 . . ?
C6A C7A C8A 118.2(2) . . ?
C6A C7A H7A 120.9 . . ?
C8A C7A H7A 120.9 . . ?
C9A C8A C7A 123.9(2) . . ?
C9A C8A H8A 118.1 . . ?
C7A C8A H8A 118.1 . . ?
C8A C9A C10A 119.23(19) . . ?
C8A C9A C13A 114.69(19) . . ?
C10A C9A C13A 125.28(18) . . ?
C5A C10A C1A 114.28(18) . . ?
C5A C10A C9A 116.25(18) . . ?
C1A C10A C9A 129.41(18) . . ?
N1A C11A H11A 109.5 . . ?
N1A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
N1A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
N1A C12A H12A 109.5 . . ?
N1A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
N1A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
O1A C13A C9A 118.66(18) . . ?
O1A C13A C14A 118.62(18) . . ?
C9A C13A C14A 122.68(17) . . ?
C16A C14A C13A 113.40(17) . . ?
C16A C14A C15A 107.91(18) . . ?
C13A C14A C15A 106.93(17) . . ?
C16A C14A C17A 111.93(18) . . ?
C13A C14A C17A 109.21(18) . . ?
C15A C14A C17A 107.13(18) . . ?
C14A C15A H15A 109.5 . . ?
C14A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C14A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C14A C16A H16A 109.5 . . ?
C14A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
C14A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C14A C17A H17A 109.5 . . ?
C14A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C14A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C1B N1B C12B 110.87(15) . . ?
C1B N1B C11B 115.50(17) . . ?
C12B N1B C11B 109.91(18) . . ?
C1B N1B H1B 105.1(15) . . ?
C12B N1B H1B 107.7(14) . . ?
C11B N1B H1B 107.3(14) . . ?
C2B C1B C10B 122.1(2) . . ?
C2B C1B N1B 116.81(19) . . ?
C10B C1B N1B 121.02(17) . . ?
C1B C2B C3B 121.0(2) . . ?
C1B C2B H2B 119.5 . . ?
C3B C2B H2B 119.5 . . ?
C4B C3B C2B 119.5(2) . . ?
C4B C3B H3B 120.3 . . ?
C2B C3B H3B 120.3 . . ?
C3B C4B C5B 121.0(2) . . ?
C3B C4B H4B 119.5 . . ?
C5B C4B H4B 119.5 . . ?
C4B C5B C6B 117.9(2) . . ?
C4B C5B C10B 121.1(2) . . ?
C6B C5B C10B 121.02(19) . . ?
C7B C6B C5B 121.0(2) . . ?
C7B C6B H6B 119.5 . . ?
C5B C6B H6B 119.5 . . ?
C6B C7B C8B 118.7(2) . . ?
C6B C7B H7B 120.7 . . ?
C8B C7B H7B 120.7 . . ?
C9B C8B C7B 123.2(2) . . ?
C9B C8B H8B 118.4 . . ?
C7B C8B H8B 118.4 . . ?
C8B C9B C10B 119.68(19) . . ?
C8B C9B C13B 114.88(19) . . ?
C10B C9B C13B 124.47(18) . . ?
C5B C10B C1B 115.28(18) . . ?
C5B C10B C9B 116.25(18) . . ?
C1B C10B C9B 128.41(19) . . ?
N1B C11B H11Y 109.5 . . ?
N1B C11B H11Z 109.5 . . ?
H11Y C11B H11Z 109.5 . . ?
N1B C11B H11X 109.5 . . ?
H11Y C11B H11X 109.5 . . ?
H11Z C11B H11X 109.5 . . ?
N1B C12B H12X 109.5 . . ?
N1B C12B H12Y 109.5 . . ?
H12X C12B H12Y 109.5 . . ?
N1B C12B H12Z 109.5 . . ?
H12X C12B H12Z 109.5 . . ?
H12Y C12B H12Z 109.5 . . ?
O1B C13B C9B 117.57(18) . . ?
O1B C13B C14B 118.92(18) . . ?
C9B C13B C14B 123.44(17) . . ?
C16B C14B C13B 113.33(17) . . ?
C16B C14B C17B 111.55(17) . . ?
C13B C14B C17B 108.98(17) . . ?
C16B C14B C15B 107.83(18) . . ?
C13B C14B C15B 107.44(17) . . ?
C17B C14B C15B 107.44(18) . . ?
C14B C15B H15X 109.5 . . ?
C14B C15B H15Y 109.5 . . ?
H15X C15B H15Y 109.5 . . ?
C14B C15B H15Z 109.5 . . ?
H15X C15B H15Z 109.5 . . ?
H15Y C15B H15Z 109.5 . . ?
C14B C16B H16Z 109.5 . . ?
C14B C16B H16X 109.5 . . ?
H16Z C16B H16X 109.5 . . ?
C14B C16B H16Y 109.5 . . ?
H16Z C16B H16Y 109.5 . . ?
H16X C16B H16Y 109.5 . . ?
C14B C17B H17Z 109.5 . . ?
C14B C17B H17X 109.5 . . ?
H17Z C17B H17X 109.5 . . ?
C14B C17B H17Y 109.5 . . ?
H17Z C17B H17Y 109.5 . . ?
H17X C17B H17Y 109.5 . . ?
O1C S1C O3C 114.97(10) . . ?
O1C S1C O2C 114.51(10) . . ?
O3C S1C O2C 115.32(10) . . ?
O1C S1C C1C 102.62(11) . . ?
O3C S1C C1C 103.37(10) . . ?
O2C S1C C1C 103.64(11) . . ?
F3C C1C F2C 107.3(2) . . ?
F3C C1C F1C 107.08(19) . . ?
F2C C1C F1C 106.77(18) . . ?
F3C C1C S1C 112.19(16) . . ?
F2C C1C S1C 111.53(16) . . ?
F1C C1C S1C 111.70(18) . . ?
O3D S1D O1D 115.76(10) . . ?
O3D S1D O2D 114.61(10) . . ?
O1D S1D O2D 114.71(10) . . ?
O3D S1D C1D 103.34(10) . . ?
O1D S1D C1D 102.87(10) . . ?
O2D S1D C1D 103.06(11) . . ?
F2D C1D F1D 107.65(19) . . ?
F2D C1D F3D 106.87(18) . . ?
F1D C1D F3D 106.67(19) . . ?
F2D C1D S1D 111.41(17) . . ?
F1D C1D S1D 112.19(15) . . ?
F3D C1D S1D 111.74(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1A H1A O1A 0.91(2) 1.77(2) 2.641(2) 159(2) .
N1B H1B O1B 0.93(2) 1.78(2) 2.658(2) 157(2) .

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 984804'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_10HBF4
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
N,N-Dimethyl-N-(8-benzoylnaphth-1-yl)ammonium tetrafluoroborate, 10-H.BF4
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 B F4 N O'
_chemical_formula_weight         363.15

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'
B B 0.0013 0.0007 '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           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   13.6452(5)
_cell_length_b                   13.5547(4)
_cell_length_c                   18.2545(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3376.3(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2347
_cell_measurement_theta_min      2.9790
_cell_measurement_theta_max      28.9518


_exptl_crystal_description       'thick needle'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3952
_exptl_crystal_size_mid          0.1400
_exptl_crystal_size_min          0.0804
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1504
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_min  0.98994
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
The x,y,z and Uiso of the (N)-H atom were allowed to refine.
All the other H atoms were treated with a riding model. 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10610
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         29.02
_reflns_number_total             3948
_reflns_number_gt                2983
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_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)+(0.0512P)²+3.4888P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3948
_refine_ls_number_parameters     270
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0767
_refine_ls_wR_factor_ref         0.1660
_refine_ls_wR_factor_gt          0.1518
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.126
_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
F1A F 0.0460(2) 0.8247(3) 0.4582(4) 0.083(2) Uani 0.567(5) 1 d PD A 1
F1B F 0.0881(5) 0.8427(3) 0.4999(3) 0.0608(19) Uani 0.433(5) 1 d PD A 2
F2 F 0.13241(16) 0.68668(13) 0.44389(17) 0.0842(8) Uani 1 1 d D A .
F3A F 0.1896(3) 0.8385(3) 0.3993(2) 0.0499(12) Uani 0.567(5) 1 d PD A 1
F3B F 0.0830(4) 0.7976(4) 0.3869(2) 0.082(2) Uani 0.433(5) 1 d PD A 2
F4A F 0.1858(3) 0.7947(3) 0.51520(17) 0.0752(18) Uani 0.567(5) 1 d PD A 1
F4B F 0.2289(3) 0.8182(5) 0.4350(6) 0.105(4) Uani 0.433(5) 1 d PD A 2
H1 H 0.1149(19) 0.487(2) 0.0758(14) 0.025(7) Uiso 1 1 d . . .
O1 O 0.02832(13) 0.52595(14) 0.14404(10) 0.0337(5) Uani 1 1 d . . .
N1 N 0.16811(15) 0.45330(15) 0.05801(11) 0.0249(5) Uani 1 1 d . . .
C1 C 0.25353(17) 0.51254(17) 0.08157(13) 0.0219(5) Uani 1 1 d . . .
C2 C 0.33176(19) 0.51823(19) 0.03553(14) 0.0274(6) Uani 1 1 d . . .
H2 H 0.3298 0.4849 -0.0102 0.033 Uiso 1 1 calc R . .
C3 C 0.41525(18) 0.57275(19) 0.05474(15) 0.0304(6) Uani 1 1 d . . .
H3 H 0.4693 0.5766 0.0221 0.036 Uiso 1 1 calc R . .
C4 C 0.41826(18) 0.61988(18) 0.12012(14) 0.0272(6) Uani 1 1 d . . .
H4 H 0.4749 0.6567 0.1331 0.033 Uiso 1 1 calc R . .
C5 C 0.33864(17) 0.61521(17) 0.16931(13) 0.0232(5) Uani 1 1 d . . .
C6 C 0.34586(19) 0.66689(18) 0.23637(14) 0.0288(6) Uani 1 1 d . . .
H6 H 0.4034 0.7039 0.2466 0.035 Uiso 1 1 calc R . .
C7 C 0.2724(2) 0.66465(19) 0.28627(14) 0.0321(6) Uani 1 1 d . . .
H7 H 0.2776 0.7008 0.3307 0.039 Uiso 1 1 calc R . .
C8 C 0.18911(19) 0.60840(19) 0.27133(14) 0.0296(6) Uani 1 1 d . . .
H8 H 0.1387 0.6053 0.3071 0.036 Uiso 1 1 calc R . .
C9 C 0.17707(17) 0.55726(17) 0.20687(13) 0.0236(5) Uani 1 1 d . . .
C10 C 0.25233(17) 0.56010(16) 0.15181(13) 0.0206(5) Uani 1 1 d . . .
C12 C 0.1681(2) 0.35383(19) 0.09368(16) 0.0369(7) Uani 1 1 d . . .
H12C H 0.2215 0.3139 0.0735 0.055 Uiso 1 1 calc R . .
H12A H 0.1053 0.3210 0.0843 0.055 Uiso 1 1 calc R . .
H12B H 0.1774 0.3615 0.1466 0.055 Uiso 1 1 calc R . .
C11 C 0.1547(2) 0.4411(2) -0.02324(14) 0.0335(6) Uani 1 1 d . . .
H11A H 0.1603 0.5056 -0.0472 0.050 Uiso 1 1 calc R . .
H11B H 0.0898 0.4132 -0.0331 0.050 Uiso 1 1 calc R . .
H11C H 0.2053 0.3968 -0.0424 0.050 Uiso 1 1 calc R . .
C13 C 0.07812(18) 0.50992(18) 0.19886(13) 0.0260(5) Uani 1 1 d . . .
C14 C 0.04100(18) 0.44375(18) 0.25740(14) 0.0260(5) Uani 1 1 d . . .
C15 C 0.0997(2) 0.40859(19) 0.31429(13) 0.0284(6) Uani 1 1 d . . .
H15 H 0.1658 0.4298 0.3183 0.034 Uiso 1 1 calc R . .
C16 C 0.0618(2) 0.3430(2) 0.36486(15) 0.0364(7) Uani 1 1 d . . .
H16 H 0.1017 0.3203 0.4041 0.044 Uiso 1 1 calc R . .
C17 C -0.0339(2) 0.3104(2) 0.35860(18) 0.0442(8) Uani 1 1 d . . .
H17 H -0.0599 0.2654 0.3934 0.053 Uiso 1 1 calc R . .
C18 C -0.0914(2) 0.3437(2) 0.30159(18) 0.0447(8) Uani 1 1 d . . .
H18 H -0.1568 0.3205 0.2969 0.054 Uiso 1 1 calc R . .
C19 C -0.05514(19) 0.4098(2) 0.25151(17) 0.0354(6) Uani 1 1 d . . .
H19 H -0.0957 0.4326 0.2127 0.042 Uiso 1 1 calc R . .
B1 B 0.13694(15) 0.78666(14) 0.44978(12) 0.0311(7) Uani 1 1 d 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
F1A B1 1.352(2) . ?
F1B B1 1.363(2) . ?
F2 B1 1.3609(19) . ?
F3A B1 1.364(2) . ?
F3B B1 1.372(2) . ?
F4A B1 1.372(2) . ?
F4B B1 1.353(2) . ?
O1 C13 1.229(3) . ?
N1 C1 1.479(3) . ?
N1 C12 1.497(3) . ?
N1 C11 1.504(3) . ?
N1 H1 0.92(3) . ?
C1 C2 1.361(3) . ?
C1 C10 1.435(3) . ?
C2 C3 1.402(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.354(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.411(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.414(3) . ?
C5 C10 1.431(3) . ?
C6 C7 1.355(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.396(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.376(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.438(3) . ?
C9 C13 1.502(3) . ?
C12 H12C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 C14 1.484(4) . ?
C14 C19 1.394(3) . ?
C14 C15 1.395(4) . ?
C15 C16 1.381(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.373(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

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
C1 N1 C12 111.25(19) . . ?
C1 N1 C11 116.2(2) . . ?
C12 N1 C11 109.3(2) . . ?
C1 N1 H1 104.4(16) . . ?
C12 N1 H1 107.3(16) . . ?
C11 N1 H1 107.9(16) . . ?
C2 C1 C10 122.4(2) . . ?
C2 C1 N1 118.0(2) . . ?
C10 C1 N1 119.6(2) . . ?
C1 C2 C3 120.8(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 121.1(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 118.4(2) . . ?
C4 C5 C10 121.0(2) . . ?
C6 C5 C10 120.6(2) . . ?
C7 C6 C5 121.3(2) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 118.9(2) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C9 C8 C7 122.7(2) . . ?
C9 C8 H8 118.7 . . ?
C7 C8 H8 118.7 . . ?
C8 C9 C10 120.0(2) . . ?
C8 C9 C13 114.0(2) . . ?
C10 C9 C13 125.8(2) . . ?
C5 C10 C1 115.1(2) . . ?
C5 C10 C9 116.5(2) . . ?
C1 C10 C9 128.4(2) . . ?
N1 C12 H12C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
H12C C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12C C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C13 C14 120.3(2) . . ?
O1 C13 C9 120.1(2) . . ?
C14 C13 C9 119.7(2) . . ?
C19 C14 C15 119.0(2) . . ?
C19 C14 C13 117.7(2) . . ?
C15 C14 C13 123.1(2) . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.2(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 119.7(3) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C19 C18 C17 120.7(3) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C14 120.2(3) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
F1A B1 F4B 138.9(4) . . ?
F1A B1 F2 110.3(3) . . ?
F4B B1 F2 109.9(3) . . ?
F1A B1 F1B 42.5(3) . . ?
F4B B1 F1B 114.3(4) . . ?
F2 B1 F1B 125.9(3) . . ?
F1A B1 F3A 111.3(3) . . ?
F4B B1 F3A 38.2(4) . . ?
F2 B1 F3A 118.9(3) . . ?
F1B B1 F3A 115.1(3) . . ?
F1A B1 F3B 64.0(4) . . ?
F4B B1 F3B 107.2(5) . . ?
F2 B1 F3B 91.0(3) . . ?
F1B B1 F3B 103.8(4) . . ?
F3A B1 F3B 70.2(3) . . ?
F1A B1 F4A 108.5(4) . . ?
F4B B1 F4A 72.4(5) . . ?
F2 B1 F4A 99.8(2) . . ?
F1B B1 F4A 67.0(4) . . ?
F3A B1 F4A 107.0(3) . . ?
F3B B1 F4A 168.7(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.92(3) 1.80(3) 2.660(3) 156(2) .

_diffrn_measured_fraction_theta_max 0.877
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.053
_vrf_PLAT244_3crpabzz            
; 
PROBLEM: Low   'Solvent' Ueq for B1       

RESPONSE: the BF4 is disordered so the ADPs of the
F atoms are quite large.
;
_vrf_PLAT779_3crpabzz            
; 
PROBLEM:  uspect or Irrelevant (Bond) Angle in CIF       

RESPONSE: the BF4 is disordered between two orientations, A and B.
;
_database_code_depnum_ccdc_archive 'CCDC 984805'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_11Htriflate

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
2-Hydroxy-2-trifluoromethyl-1,1-dimethyl-1,2-dihydrobenzo[cd]indol-1-ium
triflate monohydrate   11-H.triflate.H2O
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H13 F3 N O, C F3 O3 S , H2 O'
_chemical_formula_sum            'C15 H15 F6 N O5 S'
_chemical_formula_weight         435.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   10.3782(7)
_cell_length_b                   17.4219(8)
_cell_length_c                   9.9913(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.321(7)
_cell_angle_gamma                90.00
_cell_volume                     1757.90(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    19516
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9223
_exptl_absorpt_correction_T_max  0.9731
_exptl_absorpt_process_details   
; 
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_exptl_special_details           ?

_diffrn_ambient_temperature      100
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Mitegen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            22668
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4015
_reflns_number_gt                3459
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;

_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. 

The geometry of the water molecule was restrained
DFIX 0.85 0.005 O2 H14 O2 H15
DFIX 1.34 0.005 H14 H15
;

_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)+(0.0301P)²+1.2144P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4015
_refine_ls_number_parameters     266
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0783
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.056
_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
S1 S 0.13864(4) 0.118471(19) 0.88413(4) 0.01576(9) Uani 1 1 d . . .
F1 F 0.67748(9) 0.22054(5) 0.85229(10) 0.0239(2) Uani 1 1 d . . .
F2 F 0.58189(9) 0.30443(5) 0.95607(9) 0.01995(19) Uani 1 1 d . . .
F3 F 0.51481(9) 0.28698(5) 0.73715(9) 0.0252(2) Uani 1 1 d . . .
F4 F 0.23856(12) 0.24038(6) 1.02272(11) 0.0380(3) Uani 1 1 d . . .
F5 F 0.36150(11) 0.19130(7) 0.89921(13) 0.0448(3) Uani 1 1 d . . .
F6 F 0.18724(13) 0.25545(6) 0.80360(11) 0.0400(3) Uani 1 1 d . . .
O1 O 0.76659(11) 0.32492(6) 0.70656(11) 0.0189(2) Uani 1 1 d . . .
H13 H 0.7859(19) 0.3596(11) 0.6539(19) 0.023 Uiso 1 1 d . . .
O2 O 0.82921(16) 0.41578(7) 0.53535(15) 0.0385(3) Uani 1 1 d D . .
O3 O 0.13996(11) 0.09089(6) 0.74888(11) 0.0211(2) Uani 1 1 d . . .
O4 O 0.20784(13) 0.07096(6) 0.99604(12) 0.0283(3) Uani 1 1 d . . .
O5 O 0.01065(11) 0.14575(7) 0.89878(12) 0.0258(3) Uani 1 1 d . . .
N1 N 0.83148(12) 0.37069(6) 0.94620(12) 0.0136(2) Uani 1 1 d . . .
C1 C 0.77941(14) 0.43712(7) 1.01092(14) 0.0132(3) Uani 1 1 d . . .
C2 C 0.82188(14) 0.46662(8) 1.13904(15) 0.0159(3) Uani 1 1 d . . .
H2 H 0.8869 0.4415 1.2075 0.019 Uiso 1 1 calc R . .
C3 C 0.76361(15) 0.53754(8) 1.16549(15) 0.0174(3) Uani 1 1 d . . .
H3 H 0.7895 0.5595 1.2547 0.021 Uiso 1 1 calc R . .
C4 C 0.67163(15) 0.57521(8) 1.06697(15) 0.0167(3) Uani 1 1 d . . .
H4 H 0.6385 0.6235 1.0879 0.020 Uiso 1 1 calc R . .
C5 C 0.62512(14) 0.54295(8) 0.93363(15) 0.0146(3) Uani 1 1 d . . .
C6 C 0.52851(15) 0.57208(8) 0.82141(15) 0.0179(3) Uani 1 1 d . . .
H6 H 0.4885 0.6204 0.8291 0.021 Uiso 1 1 calc R . .
C7 C 0.49218(15) 0.53082(9) 0.70121(16) 0.0199(3) Uani 1 1 d . . .
H7 H 0.4273 0.5518 0.6273 0.024 Uiso 1 1 calc R . .
C8 C 0.54792(15) 0.45813(8) 0.68314(15) 0.0180(3) Uani 1 1 d . . .
H8 H 0.5194 0.4300 0.6001 0.022 Uiso 1 1 calc R . .
C9 C 0.64400(14) 0.42997(8) 0.78917(14) 0.0141(3) Uani 1 1 d . . .
C10 C 0.68131(14) 0.47223(7) 0.91119(14) 0.0129(3) Uani 1 1 d . . .
C11 C 0.87481(16) 0.30428(8) 1.04213(16) 0.0195(3) Uani 1 1 d . . .
H11A H 0.9505 0.3198 1.1153 0.029 Uiso 1 1 calc R . .
H11B H 0.9006 0.2612 0.9908 0.029 Uiso 1 1 calc R . .
H11C H 0.8016 0.2885 1.0828 0.029 Uiso 1 1 calc R . .
C12 C 0.95171(15) 0.39853(8) 0.89887(16) 0.0185(3) Uani 1 1 d . . .
H12A H 0.9272 0.4426 0.8374 0.028 Uiso 1 1 calc R . .
H12B H 0.9850 0.3571 0.8496 0.028 Uiso 1 1 calc R . .
H12C H 1.0208 0.4138 0.9789 0.028 Uiso 1 1 calc R . .
C13 C 0.71505(14) 0.35329(8) 0.80838(14) 0.0145(3) Uani 1 1 d . . .
C14 C 0.62205(15) 0.29011(8) 0.84039(15) 0.0177(3) Uani 1 1 d . . .
C15 C 0.23722(17) 0.20617(9) 0.90356(16) 0.0239(3) Uani 1 1 d . . .
H14 H 0.8892(18) 0.4029(11) 0.495(2) 0.062(8) Uiso 1 1 d D . .
H15 H 0.822(2) 0.4639(4) 0.524(2) 0.049(7) Uiso 1 1 d 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
S1 O3 1.4373(11) . ?
S1 O4 1.4426(12) . ?
S1 O5 1.4496(12) . ?
S1 C15 1.8241(16) . ?
F1 C14 1.3350(16) . ?
F2 C14 1.3393(17) . ?
F3 C14 1.3329(18) . ?
F4 C15 1.3286(18) . ?
F5 C15 1.326(2) . ?
F6 C15 1.3285(19) . ?
O1 C13 1.3476(17) . ?
O1 H13 0.85(2) . ?
O2 H14 0.847(5) . ?
O2 H15 0.847(5) . ?
N1 C1 1.4868(17) . ?
N1 C11 1.5037(18) . ?
N1 C12 1.5124(18) . ?
N1 C13 1.6375(18) . ?
C1 C2 1.355(2) . ?
C1 C10 1.391(2) . ?
C2 C3 1.4267(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.370(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.424(2) . ?
C4 H4 0.9500 . ?
C5 C10 1.4031(18) . ?
C5 C6 1.415(2) . ?
C6 C7 1.376(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.421(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.368(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.4002(19) . ?
C9 C13 1.5168(19) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.5452(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
O3 S1 O4 115.21(7) . . ?
O3 S1 O5 114.33(7) . . ?
O4 S1 O5 114.45(7) . . ?
O3 S1 C15 104.69(7) . . ?
O4 S1 C15 103.37(7) . . ?
O5 S1 C15 102.66(7) . . ?
C13 O1 H13 113.3(13) . . ?
H14 O2 H15 104.9(8) . . ?
C1 N1 C11 114.02(11) . . ?
C1 N1 C12 107.17(10) . . ?
C11 N1 C12 107.39(11) . . ?
C1 N1 C13 103.78(10) . . ?
C11 N1 C13 116.60(10) . . ?
C12 N1 C13 107.37(10) . . ?
C2 C1 C10 122.33(13) . . ?
C2 C1 N1 129.36(13) . . ?
C10 C1 N1 108.06(11) . . ?
C1 C2 C3 116.35(13) . . ?
C1 C2 H2 121.8 . . ?
C3 C2 H2 121.8 . . ?
C4 C3 C2 122.45(13) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C3 C4 C5 120.86(13) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C10 C5 C6 115.66(13) . . ?
C10 C5 C4 115.62(13) . . ?
C6 C5 C4 128.72(13) . . ?
C7 C6 C5 120.40(13) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 122.61(14) . . ?
C6 C7 H7 118.7 . . ?
C8 C7 H7 118.7 . . ?
C9 C8 C7 117.82(13) . . ?
C9 C8 H8 121.1 . . ?
C7 C8 H8 121.1 . . ?
C8 C9 C10 119.47(13) . . ?
C8 C9 C13 131.33(13) . . ?
C10 C9 C13 108.91(12) . . ?
C1 C10 C9 113.73(12) . . ?
C1 C10 C5 122.28(13) . . ?
C9 C10 C5 123.99(13) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 C9 119.57(12) . . ?
O1 C13 C14 105.69(11) . . ?
C9 C13 C14 110.18(12) . . ?
O1 C13 N1 111.00(11) . . ?
C9 C13 N1 100.74(10) . . ?
C14 C13 N1 109.45(11) . . ?
F3 C14 F1 107.32(12) . . ?
F3 C14 F2 107.76(12) . . ?
F1 C14 F2 107.80(12) . . ?
F3 C14 C13 108.60(12) . . ?
F1 C14 C13 112.84(12) . . ?
F2 C14 C13 112.29(11) . . ?
F5 C15 F6 108.41(14) . . ?
F5 C15 F4 107.91(14) . . ?
F6 C15 F4 107.79(13) . . ?
F5 C15 S1 111.03(11) . . ?
F6 C15 S1 110.43(11) . . ?
F4 C15 S1 111.16(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C1 C2 38.49(19) . . . . ?
C12 N1 C1 C2 -80.21(17) . . . . ?
C13 N1 C1 C2 166.37(14) . . . . ?
C11 N1 C1 C10 -147.27(12) . . . . ?
C12 N1 C1 C10 94.03(13) . . . . ?
C13 N1 C1 C10 -19.39(13) . . . . ?
C10 C1 C2 C3 -2.0(2) . . . . ?
N1 C1 C2 C3 171.47(13) . . . . ?
C1 C2 C3 C4 -1.3(2) . . . . ?
C2 C3 C4 C5 2.9(2) . . . . ?
C3 C4 C5 C10 -1.1(2) . . . . ?
C3 C4 C5 C6 177.87(14) . . . . ?
C10 C5 C6 C7 1.8(2) . . . . ?
C4 C5 C6 C7 -177.23(14) . . . . ?
C5 C6 C7 C8 0.2(2) . . . . ?
C6 C7 C8 C9 -1.9(2) . . . . ?
C7 C8 C9 C10 1.5(2) . . . . ?
C7 C8 C9 C13 174.51(14) . . . . ?
C2 C1 C10 C9 -175.32(13) . . . . ?
N1 C1 C10 C9 9.95(16) . . . . ?
C2 C1 C10 C5 3.9(2) . . . . ?
N1 C1 C10 C5 -170.85(12) . . . . ?
C8 C9 C10 C1 179.72(13) . . . . ?
C13 C9 C10 C1 5.26(16) . . . . ?
C8 C9 C10 C5 0.5(2) . . . . ?
C13 C9 C10 C5 -173.93(12) . . . . ?
C6 C5 C10 C1 178.71(13) . . . . ?
C4 C5 C10 C1 -2.16(19) . . . . ?
C6 C5 C10 C9 -2.2(2) . . . . ?
C4 C5 C10 C9 176.96(13) . . . . ?
C8 C9 C13 O1 48.4(2) . . . . ?
C10 C9 C13 O1 -138.04(13) . . . . ?
C8 C9 C13 C14 -74.30(19) . . . . ?
C10 C9 C13 C14 99.28(13) . . . . ?
C8 C9 C13 N1 170.18(14) . . . . ?
C10 C9 C13 N1 -16.24(13) . . . . ?
C1 N1 C13 O1 148.82(11) . . . . ?
C11 N1 C13 O1 -84.92(14) . . . . ?
C12 N1 C13 O1 35.54(14) . . . . ?
C1 N1 C13 C9 21.16(12) . . . . ?
C11 N1 C13 C9 147.43(11) . . . . ?
C12 N1 C13 C9 -92.11(12) . . . . ?
C1 N1 C13 C14 -94.90(12) . . . . ?
C11 N1 C13 C14 31.37(15) . . . . ?
C12 N1 C13 C14 151.83(11) . . . . ?
O1 C13 C14 F3 -72.16(14) . . . . ?
C9 C13 C14 F3 58.34(15) . . . . ?
N1 C13 C14 F3 168.24(10) . . . . ?
O1 C13 C14 F1 46.69(16) . . . . ?
C9 C13 C14 F1 177.19(11) . . . . ?
N1 C13 C14 F1 -72.91(14) . . . . ?
O1 C13 C14 F2 168.78(12) . . . . ?
C9 C13 C14 F2 -60.72(15) . . . . ?
N1 C13 C14 F2 49.17(15) . . . . ?
O3 S1 C15 F5 -63.20(13) . . . . ?
O4 S1 C15 F5 57.80(13) . . . . ?
O5 S1 C15 F5 177.10(12) . . . . ?
O3 S1 C15 F6 57.08(13) . . . . ?
O4 S1 C15 F6 178.08(11) . . . . ?
O5 S1 C15 F6 -62.62(13) . . . . ?
O3 S1 C15 F4 176.66(12) . . . . ?
O4 S1 C15 F4 -62.34(14) . . . . ?
O5 S1 C15 F4 56.97(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H13 O2 0.85(2) 1.68(2) 2.5232(16) 170.8(19) .
O2 H14 O5 0.847(5) 1.946(6) 2.7822(16) 169(2) 4_665
O2 H15 O4 0.847(5) 1.893(5) 2.7385(16) 175.6(19) 2_656

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.051




_database_code_depnum_ccdc_archive 'CCDC 984806'
