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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_283
_database_code_depnum_ccdc_archive 'CCDC 1479453'
_audit_update_record             
;
2016-05-12 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;
_audit_creation_date             2014-11-11
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
10-Methyl-9-(4-trifluoromethylphenyl)-9,10-dihydroacridine
_chemical_formula_moiety         '2(C21 H16 F3 N)'
_chemical_formula_sum            'C42 H32 F6 N2'
_chemical_formula_weight         678.70
_chemical_melting_point          ?
_chemical_oxdiff_formula         C10H10N
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   10.7236(3)
_cell_length_b                   12.3739(3)
_cell_length_c                   14.3134(4)
_cell_angle_alpha                109.830(2)
_cell_angle_beta                 111.959(3)
_cell_angle_gamma                90.014(2)
_cell_volume                     1639.36(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6027
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      30.6210
_cell_measurement_theta_min      2.0900
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16154
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         30.81
_diffrn_reflns_theta_min         1.77
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9999
_diffrn_measured_fraction_theta_max 0.8638
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -20.00   20.00   0.5000   20.2300
omega____ theta____ kappa____ phi______ frames
    -      -20.7920  -99.0000 -150.0000 80

#__ type_ start__ end____ width___ exp.time_
  2 omega  -14.00   16.00   0.5000   20.2300
omega____ theta____ kappa____ phi______ frames
    -      -20.7920  -99.0000  -90.0000 60

#__ type_ start__ end____ width___ exp.time_
  3 omega  -84.00  -35.00   0.5000   20.2300
omega____ theta____ kappa____ phi______ frames
    -      -20.7920 -178.0000  120.0000 98

#__ type_ start__ end____ width___ exp.time_
  4 omega  -21.00    9.00   0.5000   20.2300
omega____ theta____ kappa____ phi______ frames
    -      -20.7920  -99.0000   60.0000 60

#__ type_ start__ end____ width___ exp.time_
  5 omega    4.00   91.00   0.5000   20.2300
omega____ theta____ kappa____ phi______ frames
    -       23.2920   57.0000 -180.0000 174

#__ type_ start__ end____ width___ exp.time_
  6 omega   -2.00   96.00   0.5000   20.2300
omega____ theta____ kappa____ phi______ frames
    -       23.2920   38.0000   90.0000 196

#__ type_ start__ end____ width___ exp.time_
  7 omega  -41.00   49.00   0.5000   20.2300
omega____ theta____ kappa____ phi______ frames
    -       23.2920  -38.0000  -90.0000 180
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0572071000
_diffrn_orient_matrix_UB_12      0.0079894000
_diffrn_orient_matrix_UB_13      0.0485140000
_diffrn_orient_matrix_UB_21      0.0319929000
_diffrn_orient_matrix_UB_22      -0.0385174000
_diffrn_orient_matrix_UB_23      -0.0302157000
_diffrn_orient_matrix_UB_31      0.0300046000
_diffrn_orient_matrix_UB_32      0.0473947000
_diffrn_orient_matrix_UB_33      -0.0054363000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                7301
_reflns_number_total             8885
_reflns_odcompleteness_completeness 99.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     611
_refine_ls_number_reflns         8885
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1200P)²+0.2100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1700
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.4213(6) 0.3430(4) 0.9330(4) 0.108(2) Uani 0.60 1 d PU A 1
F2A F 0.3793(4) 0.2719(3) 0.7682(3) 0.0679(11) Uani 0.60 1 d PU A 1
C2A C -0.16447(14) 0.57917(12) 0.45719(11) 0.0245(3) Uani 1 1 d . . .
F3 F 0.4982(5) 0.1522(3) 0.0693(3) 0.1103(17) Uani 0.75 1 d PU B 1
N1A N 0.03065(12) 0.70278(10) 0.61847(9) 0.0226(2) Uani 1 1 d . . .
N1 N 0.41217(11) -0.20279(10) 0.38149(9) 0.0227(2) Uani 1 1 d . . .
F2 F 0.6098(2) 0.2323(2) 0.2350(2) 0.0705(7) Uani 0.75 1 d PU B 1
C10 C 0.18368(17) -0.44883(13) 0.07019(12) 0.0320(3) Uani 1 1 d . . .
C16A C 0.18974(14) 0.58468(12) 0.82659(11) 0.0248(3) Uani 1 1 d . A .
C6A C -0.14167(13) 0.59495(11) 0.63657(10) 0.0212(2) Uani 1 1 d . . .
C19A C 0.08707(16) 0.35489(12) 0.77031(11) 0.0275(3) Uani 1 1 d . . .
C11 C 0.29846(18) -0.47617(12) 0.13903(13) 0.0325(3) Uani 1 1 d . . .
C6 C 0.22161(13) -0.09511(11) 0.36339(10) 0.0214(2) Uani 1 1 d . . .
C3 C 0.30022(15) -0.00629(12) 0.58712(11) 0.0273(3) Uani 1 1 d . . .
C9A C 0.04214(15) 0.83927(12) 0.89506(11) 0.0274(3) Uani 1 1 d . . .
C1A C -0.09112(13) 0.62548(11) 0.56983(10) 0.0208(2) Uani 1 1 d . . .
C5A C -0.26709(14) 0.52515(12) 0.59028(11) 0.0259(3) Uani 1 1 d . . .
C14 C 0.54157(14) -0.22439(13) 0.45007(12) 0.0283(3) Uani 1 1 d . . .
H14A H 0.5254 -0.2747 0.4840 0.042 Uiso 1 1 calc R . .
H14B H 0.5937 -0.1521 0.5046 0.042 Uiso 1 1 calc R . .
H14C H 0.5909 -0.2606 0.4068 0.042 Uiso 1 1 calc R . .
C13 C 0.33856(13) -0.28601(11) 0.27765(10) 0.0221(2) Uani 1 1 d . . .
C8 C 0.22340(14) -0.25729(11) 0.20709(10) 0.0224(3) Uani 1 1 d . . .
C16 C 0.24869(14) 0.06525(12) 0.24939(11) 0.0251(3) Uani 1 1 d . B .
C3A C -0.28681(15) 0.50621(12) 0.41283(11) 0.0270(3) Uani 1 1 d . . .
C13A C 0.06078(13) 0.78589(11) 0.72225(10) 0.0220(2) Uani 1 1 d . . .
C1 C 0.33905(13) -0.12545(11) 0.43027(10) 0.0207(2) Uani 1 1 d . . .
C9 C 0.14689(15) -0.33932(12) 0.10492(11) 0.0273(3) Uani 1 1 d . . .
C21 C 0.48043(18) 0.19448(14) 0.15866(15) 0.0376(4) Uani 1 1 d . . .
C10A C 0.11336(16) 0.94874(13) 0.92972(12) 0.0317(3) Uani 1 1 d . . .
C4A C -0.34021(15) 0.48015(13) 0.47869(12) 0.0287(3) Uani 1 1 d . . .
C8A C 0.01633(13) 0.75730(11) 0.79296(10) 0.0225(3) Uani 1 1 d . . .
C12 C 0.37550(15) -0.39670(12) 0.24220(12) 0.0277(3) Uani 1 1 d . . .
C15A C 0.04978(13) 0.55047(11) 0.77850(10) 0.0213(2) Uani 1 1 d . . .
C21A C 0.32192(18) 0.30565(14) 0.84160(15) 0.0376(4) Uani 1 1 d . . .
C17A C 0.27859(15) 0.50536(13) 0.84678(12) 0.0271(3) Uani 1 1 d . . .
C20 C 0.36310(14) -0.08475(12) 0.17347(11) 0.0247(3) Uani 1 1 d . B .
F1 F 0.4305(3) 0.2919(2) 0.1666(4) 0.1062(11) Uani 0.75 1 d PU B 1
C17 C 0.31682(15) 0.14492(12) 0.22975(11) 0.0272(3) Uani 1 1 d . . .
C4 C 0.18121(15) 0.01997(13) 0.52138(12) 0.0282(3) Uani 1 1 d . . .
C14A C 0.09161(15) 0.72454(13) 0.54985(12) 0.0282(3) Uani 1 1 d . . .
H14D H 0.0868 0.6526 0.4939 0.042 Uiso 1 1 calc R . .
H14E H 0.1850 0.7587 0.5928 0.042 Uiso 1 1 calc R . .
H14F H 0.0432 0.7767 0.5176 0.042 Uiso 1 1 calc R . .
C20A C -0.00063(14) 0.43471(12) 0.75061(11) 0.0251(3) Uani 1 1 d . . .
C5 C 0.14252(14) -0.02521(12) 0.40970(11) 0.0259(3) Uani 1 1 d . . .
C18A C 0.22690(15) 0.39082(12) 0.81889(11) 0.0260(3) Uani 1 1 d . A .
C11A C 0.15948(16) 0.97619(13) 0.86088(13) 0.0322(3) Uani 1 1 d . . .
C19 C 0.43170(15) -0.00541(13) 0.15293(12) 0.0269(3) Uani 1 1 d . . .
C7A C -0.05248(13) 0.63550(11) 0.75625(10) 0.0215(2) Uani 1 1 d . . .
C15 C 0.27135(13) -0.05039(11) 0.22170(10) 0.0213(2) Uani 1 1 d . . .
C12A C 0.13318(15) 0.89650(12) 0.75764(12) 0.0275(3) Uani 1 1 d . . .
C7 C 0.19120(13) -0.13523(11) 0.24370(10) 0.0216(2) Uani 1 1 d . B .
C18 C 0.40794(14) 0.10915(12) 0.18113(11) 0.0261(3) Uani 1 1 d . B .
C2 C 0.37812(14) -0.07950(12) 0.54256(11) 0.0244(3) Uani 1 1 d . . .
F3A F 0.2608(3) 0.2032(2) 0.8255(4) 0.0774(9) Uani 0.60 1 d PU A 1
F3B F 0.2913(5) 0.2635(5) 0.9084(5) 0.0802(13) Uani 0.40 1 d PU A 2
F2B F 0.3292(8) 0.2320(6) 0.7642(4) 0.119(3) Uani 0.40 1 d PU A 2
F1B F 0.4486(5) 0.3566(6) 0.9109(6) 0.0650(19) Uani 0.40 1 d PU A 2
F3C F 0.5419(10) 0.2797(6) 0.2314(4) 0.080(2) Uani 0.25 1 d PU B 2
F1C F 0.3769(6) 0.2255(5) 0.0800(5) 0.0563(14) Uani 0.25 1 d PU B 2
F2C F 0.5452(8) 0.1468(8) 0.0971(8) 0.060(2) Uani 0.25 1 d PU B 2
H7 H 0.0741(15) -0.1394(12) 0.1925(11) 0.008(3) Uiso 1 1 d . . .
H7A H -0.1192(14) 0.6407(12) 0.8061(11) 0.007(3) Uiso 1 1 d . . .
H16A H 0.228(2) 0.6662(17) 0.8472(15) 0.033(5) Uiso 1 1 d . . .
H16 H 0.186(2) 0.0919(16) 0.2864(15) 0.031(4) Uiso 1 1 d . . .
H17A H 0.377(2) 0.5333(17) 0.8861(16) 0.039(5) Uiso 1 1 d . . .
H19A H 0.053(2) 0.2701(17) 0.7521(15) 0.034(5) Uiso 1 1 d . . .
H20 H 0.3793(19) -0.1640(16) 0.1514(14) 0.029(4) Uiso 1 1 d . . .
H19 H 0.490(2) -0.0320(16) 0.1139(15) 0.034(5) Uiso 1 1 d . . .
H17 H 0.304(2) 0.2304(18) 0.2529(17) 0.041(5) Uiso 1 1 d . . .
H20A H -0.101(2) 0.4077(16) 0.7124(15) 0.029(4) Uiso 1 1 d . . .
H12 H 0.455(2) -0.4168(17) 0.2919(16) 0.035(5) Uiso 1 1 d . . .
H5A H -0.303(2) 0.5089(17) 0.6384(16) 0.037(5) Uiso 1 1 d . . .
H10A H 0.131(2) 1.0050(17) 1.0015(17) 0.039(5) Uiso 1 1 d . . .
H2A H -0.131(2) 0.5980(16) 0.4110(15) 0.032(5) Uiso 1 1 d . . .
H4A H -0.423(2) 0.4306(18) 0.4516(17) 0.043(5) Uiso 1 1 d . . .
H11 H 0.330(2) -0.5534(18) 0.1165(16) 0.040(5) Uiso 1 1 d . . .
H3A H -0.333(2) 0.4752(17) 0.3372(17) 0.035(5) Uiso 1 1 d . . .
H11A H 0.215(2) 1.0524(18) 0.8821(16) 0.041(5) Uiso 1 1 d . . .
H9 H 0.063(2) -0.3217(16) 0.0526(15) 0.032(5) Uiso 1 1 d . . .
H12A H 0.161(2) 0.9194(17) 0.7076(16) 0.036(5) Uiso 1 1 d . . .
H4 H 0.128(2) 0.0742(18) 0.5509(17) 0.042(5) Uiso 1 1 d . . .
H5 H 0.055(2) -0.0083(17) 0.3593(16) 0.036(5) Uiso 1 1 d . . .
H9A H 0.009(2) 0.8214(16) 0.9453(15) 0.035(5) Uiso 1 1 d . . .
H3 H 0.332(2) 0.0227(16) 0.6636(16) 0.032(5) Uiso 1 1 d . . .
H10 H 0.130(2) -0.5032(18) -0.0016(17) 0.042(5) Uiso 1 1 d . . .
H2 H 0.457(2) -0.0997(16) 0.5885(15) 0.029(4) 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
F1A C21A 1.268(5) . ?
F2A C21A 1.357(3) . ?
C2A C3A 1.388(2) . ?
C2A C1A 1.4040(18) . ?
C2A H2A 0.953(19) . ?
F3 C21 1.294(4) . ?
N1A C1A 1.4044(17) . ?
N1A C13A 1.4046(17) . ?
N1A C14A 1.4575(16) . ?
N1 C1 1.4053(17) . ?
N1 C13 1.4058(17) . ?
N1 C14 1.4560(17) . ?
F2 C21 1.362(3) . ?
C10 C11 1.386(2) . ?
C10 C9 1.389(2) . ?
C10 H10 0.96(2) . ?
C16A C15A 1.3911(19) . ?
C16A C17A 1.3934(19) . ?
C16A H16A 0.991(19) . ?
C6A C5A 1.3923(19) . ?
C6A C1A 1.4075(17) . ?
C6A C7A 1.5141(18) . ?
C19A C20A 1.3895(19) . ?
C19A C18A 1.393(2) . ?
C19A H19A 1.023(19) . ?
C11 C12 1.390(2) . ?
C11 H11 1.00(2) . ?
C6 C5 1.3924(19) . ?
C6 C1 1.4091(17) . ?
C6 C7 1.5141(17) . ?
C3 C4 1.389(2) . ?
C3 C2 1.390(2) . ?
C3 H3 0.947(19) . ?
C9A C10A 1.387(2) . ?
C9A C8A 1.3902(18) . ?
C9A H9A 1.00(2) . ?
C5A C4A 1.391(2) . ?
C5A H5A 0.97(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13 C12 1.4034(18) . ?
C13 C8 1.4079(18) . ?
C8 C9 1.3917(18) . ?
C8 C7 1.5079(18) . ?
C16 C17 1.3878(19) . ?
C16 C15 1.3968(18) . ?
C16 H16 1.00(2) . ?
C3A C4A 1.389(2) . ?
C3A H3A 0.94(2) . ?
C13A C12A 1.4027(18) . ?
C13A C8A 1.4072(18) . ?
C1 C2 1.3995(18) . ?
C9 H9 1.012(19) . ?
C21 F3C 1.171(5) . ?
C21 F1 1.306(2) . ?
C21 F2C 1.309(7) . ?
C21 F1C 1.417(5) . ?
C21 C18 1.497(2) . ?
C10A C11A 1.387(2) . ?
C10A H10A 0.97(2) . ?
C4A H4A 0.95(2) . ?
C8A C7A 1.5047(18) . ?
C12 H12 0.98(2) . ?
C15A C20A 1.3976(18) . ?
C15A C7A 1.5420(18) . ?
C21A F2B 1.202(5) . ?
C21A F3A 1.333(3) . ?
C21A F1B 1.339(6) . ?
C21A F3B 1.367(4) . ?
C21A C18A 1.497(2) . ?
C17A C18A 1.388(2) . ?
C17A H17A 0.99(2) . ?
C20 C15 1.3909(19) . ?
C20 C19 1.3959(18) . ?
C20 H20 0.961(18) . ?
C17 C18 1.391(2) . ?
C17 H17 1.02(2) . ?
C4 C5 1.392(2) . ?
C4 H4 0.97(2) . ?
C14A H14D 0.9600 . ?
C14A H14E 0.9600 . ?
C14A H14F 0.9600 . ?
C20A H20A 1.00(2) . ?
C5 H5 1.02(2) . ?
C11A C12A 1.391(2) . ?
C11A H11A 1.00(2) . ?
C19 C18 1.388(2) . ?
C19 H19 0.98(2) . ?
C7A H7A 1.173(14) . ?
C15 C7 1.5382(17) . ?
C12A H12A 0.99(2) . ?
C7 H7 1.184(14) . ?
C2 H2 0.955(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
C3A C2A C1A 120.11(12) . . ?
C3A C2A H2A 119.8(12) . . ?
C1A C2A H2A 120.1(12) . . ?
C1A N1A C13A 117.31(11) . . ?
C1A N1A C14A 118.98(11) . . ?
C13A N1A C14A 119.52(11) . . ?
C1 N1 C13 117.34(11) . . ?
C1 N1 C14 118.90(11) . . ?
C13 N1 C14 119.56(11) . . ?
C11 C10 C9 119.03(13) . . ?
C11 C10 H10 121.5(13) . . ?
C9 C10 H10 119.4(13) . . ?
C15A C16A C17A 120.85(13) . . ?
C15A C16A H16A 120.5(11) . . ?
C17A C16A H16A 118.7(12) . . ?
C5A C6A C1A 119.44(12) . . ?
C5A C6A C7A 122.78(11) . . ?
C1A C6A C7A 117.71(11) . . ?
C20A C19A C18A 119.58(13) . . ?
C20A C19A H19A 122.4(12) . . ?
C18A C19A H19A 118.0(11) . . ?
C10 C11 C12 121.13(14) . . ?
C10 C11 H11 121.5(12) . . ?
C12 C11 H11 117.3(12) . . ?
C5 C6 C1 119.41(12) . . ?
C5 C6 C7 122.63(12) . . ?
C1 C6 C7 117.88(11) . . ?
C4 C3 C2 120.85(13) . . ?
C4 C3 H3 122.7(12) . . ?
C2 C3 H3 116.5(12) . . ?
C10A C9A C8A 121.20(14) . . ?
C10A C9A H9A 117.9(11) . . ?
C8A C9A H9A 120.9(11) . . ?
C2A C1A N1A 122.07(11) . . ?
C2A C1A C6A 119.20(12) . . ?
N1A C1A C6A 118.72(11) . . ?
C4A C5A C6A 121.18(13) . . ?
C4A C5A H5A 120.8(12) . . ?
C6A C5A H5A 118.0(12) . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C13 N1 122.30(12) . . ?
C12 C13 C8 118.96(12) . . ?
N1 C13 C8 118.74(11) . . ?
C9 C8 C13 119.76(13) . . ?
C9 C8 C7 122.07(12) . . ?
C13 C8 C7 118.11(11) . . ?
C17 C16 C15 120.76(13) . . ?
C17 C16 H16 119.3(11) . . ?
C15 C16 H16 119.9(11) . . ?
C2A C3A C4A 120.87(13) . . ?
C2A C3A H3A 118.3(12) . . ?
C4A C3A H3A 120.9(12) . . ?
C12A C13A N1A 122.26(12) . . ?
C12A C13A C8A 118.90(12) . . ?
N1A C13A C8A 118.84(11) . . ?
C2 C1 N1 122.04(12) . . ?
C2 C1 C6 119.33(12) . . ?
N1 C1 C6 118.63(11) . . ?
C10 C9 C8 121.10(14) . . ?
C10 C9 H9 117.2(10) . . ?
C8 C9 H9 121.7(10) . . ?
F3C C21 F3 125.2(4) . . ?
F3C C21 F1 60.6(5) . . ?
F3 C21 F1 110.7(3) . . ?
F3C C21 F2C 113.5(6) . . ?
F3 C21 F2C 23.7(5) . . ?
F1 C21 F2C 126.1(4) . . ?
F3C C21 F2 42.3(5) . . ?
F3 C21 F2 103.0(3) . . ?
F1 C21 F2 101.7(2) . . ?
F2C C21 F2 81.7(5) . . ?
F3C C21 F1C 108.4(5) . . ?
F3 C21 F1C 72.7(3) . . ?
F1 C21 F1C 49.7(3) . . ?
F2C C21 F1C 95.9(5) . . ?
F2 C21 F1C 141.8(2) . . ?
F3C C21 C18 117.5(3) . . ?
F3 C21 C18 114.5(2) . . ?
F1 C21 C18 114.62(16) . . ?
F2C C21 C18 113.8(4) . . ?
F2 C21 C18 110.96(15) . . ?
F1C C21 C18 104.9(2) . . ?
C11A C10A C9A 119.05(13) . . ?
C11A C10A H10A 120.9(12) . . ?
C9A C10A H10A 120.1(12) . . ?
C3A C4A C5A 119.08(13) . . ?
C3A C4A H4A 123.4(13) . . ?
C5A C4A H4A 117.4(13) . . ?
C9A C8A C13A 119.77(13) . . ?
C9A C8A C7A 122.21(12) . . ?
C13A C8A C7A 117.96(11) . . ?
C11 C12 C13 120.00(14) . . ?
C11 C12 H12 121.2(11) . . ?
C13 C12 H12 118.8(11) . . ?
C16A C15A C20A 118.81(12) . . ?
C16A C15A C7A 122.70(11) . . ?
C20A C15A C7A 118.48(12) . . ?
F2B C21A F1A 121.9(4) . . ?
F2B C21A F3A 70.0(5) . . ?
F1A C21A F3A 109.9(3) . . ?
F2B C21A F1B 107.7(5) . . ?
F1A C21A F1B 24.9(4) . . ?
F3A C21A F1B 127.3(3) . . ?
F2B C21A F2A 31.1(5) . . ?
F1A C21A F2A 105.0(4) . . ?
F3A C21A F2A 100.2(2) . . ?
F1B C21A F2A 83.6(4) . . ?
F2B C21A F3B 114.2(5) . . ?
F1A C21A F3B 72.5(4) . . ?
F3A C21A F3B 47.5(2) . . ?
F1B C21A F3B 96.9(4) . . ?
F2A C21A F3B 138.4(3) . . ?
F2B C21A C18A 116.3(3) . . ?
F1A C21A C18A 115.4(3) . . ?
F3A C21A C18A 114.20(17) . . ?
F1B C21A C18A 113.0(3) . . ?
F2A C21A C18A 110.84(19) . . ?
F3B C21A C18A 107.1(2) . . ?
C18A C17A C16A 119.63(13) . . ?
C18A C17A H17A 121.1(12) . . ?
C16A C17A H17A 119.1(12) . . ?
C15 C20 C19 120.82(13) . . ?
C15 C20 H20 121.2(11) . . ?
C19 C20 H20 118.0(11) . . ?
C16 C17 C18 119.70(13) . . ?
C16 C17 H17 121.1(12) . . ?
C18 C17 H17 119.1(12) . . ?
C3 C4 C5 119.12(13) . . ?
C3 C4 H4 122.2(12) . . ?
C5 C4 H4 118.5(12) . . ?
N1A C14A H14D 109.5 . . ?
N1A C14A H14E 109.5 . . ?
H14D C14A H14E 109.5 . . ?
N1A C14A H14F 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
C19A C20A C15A 120.81(13) . . ?
C19A C20A H20A 119.4(11) . . ?
C15A C20A H20A 119.7(11) . . ?
C4 C5 C6 121.09(13) . . ?
C4 C5 H5 121.0(11) . . ?
C6 C5 H5 117.9(11) . . ?
C17A C18A C19A 120.32(13) . . ?
C17A C18A C21A 119.81(14) . . ?
C19A C18A C21A 119.87(13) . . ?
C10A C11A C12A 120.95(14) . . ?
C10A C11A H11A 123.0(12) . . ?
C12A C11A H11A 116.0(12) . . ?
C18 C19 C20 119.48(13) . . ?
C18 C19 H19 120.4(11) . . ?
C20 C19 H19 119.9(11) . . ?
C8A C7A C6A 108.84(10) . . ?
C8A C7A C15A 112.51(11) . . ?
C6A C7A C15A 110.23(10) . . ?
C8A C7A H7A 106.1(7) . . ?
C6A C7A H7A 110.2(7) . . ?
C15A C7A H7A 108.9(7) . . ?
C20 C15 C16 118.86(12) . . ?
C20 C15 C7 122.66(12) . . ?
C16 C15 C7 118.46(12) . . ?
C11A C12A C13A 120.11(13) . . ?
C11A C12A H12A 119.9(12) . . ?
C13A C12A H12A 119.9(11) . . ?
C8 C7 C6 108.55(10) . . ?
C8 C7 C15 112.54(11) . . ?
C6 C7 C15 110.28(10) . . ?
C8 C7 H7 106.5(7) . . ?
C6 C7 H7 111.0(7) . . ?
C15 C7 H7 107.9(7) . . ?
C19 C18 C17 120.37(13) . . ?
C19 C18 C21 119.76(14) . . ?
C17 C18 C21 119.87(13) . . ?
C3 C2 C1 120.10(13) . . ?
C3 C2 H2 120.0(11) . . ?
C1 C2 H2 119.9(11) . . ?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method ethanol
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_418
_database_code_depnum_ccdc_archive 'CCDC 1479454'
_audit_update_record             
;
2016-05-12 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;
_audit_creation_date             2015-04-03
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        10-Methyl-9-phenyl-9,10-dihydroacridine
_chemical_formula_moiety         'C20 H17 N'
_chemical_formula_sum            'C20 H17 N'
_chemical_formula_weight         271.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         C10H10N
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   5.48181(13)
_cell_length_b                   10.7977(2)
_cell_length_c                   24.0126(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.443(2)
_cell_angle_gamma                90.00
_cell_volume                     1414.92(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3104
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      32.1620
_cell_measurement_theta_min      2.5470
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8836
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         32.46
_diffrn_reflns_theta_min         2.54
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9071
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -48.00   44.00   0.5000   14.4100
omega____ theta____ kappa____ phi______ frames
    -      -25.3885   38.0000 -150.0000 184

#__ type_ start__ end____ width___ exp.time_
  2 omega -101.00  -43.00   0.5000   14.4100
omega____ theta____ kappa____ phi______ frames
    -      -25.3885 -178.0000  -60.0000 116

#__ type_ start__ end____ width___ exp.time_
  3 omega  -89.00  -22.00   0.5000   14.4100
omega____ theta____ kappa____ phi______ frames
    -      -25.3885  -77.0000  -30.0000 134

#__ type_ start__ end____ width___ exp.time_
  4 omega  -37.00   -1.00   0.5000   14.4100
omega____ theta____ kappa____ phi______ frames
    -       27.5760  -57.0000   90.0000 72
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0540075000
_diffrn_orient_matrix_UB_12      -0.0558792000
_diffrn_orient_matrix_UB_13      -0.0106594000
_diffrn_orient_matrix_UB_21      -0.0209161000
_diffrn_orient_matrix_UB_22      -0.0183122000
_diffrn_orient_matrix_UB_23      0.0275195000
_diffrn_orient_matrix_UB_31      -0.1163955000
_diffrn_orient_matrix_UB_32      0.0292168000
_diffrn_orient_matrix_UB_33      -0.0031170000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3830
_reflns_number_total             4628
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4628
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1459
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
N1 N 0.58668(15) 0.78968(8) 0.31563(3) 0.01774(18) Uani 1 1 d . . .
C13 C 0.69031(17) 0.74953(9) 0.36818(4) 0.01665(19) Uani 1 1 d . . .
C15 C 0.78316(17) 1.04928(9) 0.39124(4) 0.01639(19) Uani 1 1 d . . .
C1 C 0.73570(17) 0.85862(9) 0.28254(4) 0.01663(19) Uani 1 1 d . . .
C8 C 0.87989(17) 0.81994(9) 0.39624(4) 0.01762(19) Uani 1 1 d . . .
C6 C 0.92145(17) 0.93407(9) 0.30900(4) 0.01682(19) Uani 1 1 d . . .
C7 C 0.94191(17) 0.94332(9) 0.37212(4) 0.01665(19) Uani 1 1 d . . .
C12 C 0.61270(19) 0.64090(9) 0.39327(4) 0.0208(2) Uani 1 1 d . . .
C16 C 0.59024(18) 1.03019(10) 0.42413(4) 0.0195(2) Uani 1 1 d . . .
C2 C 0.70916(19) 0.85194(10) 0.22392(4) 0.0204(2) Uani 1 1 d . . .
C4 C 1.0510(2) 0.99180(10) 0.21879(5) 0.0239(2) Uani 1 1 d . . .
C20 C 0.83608(19) 1.17074(10) 0.37603(4) 0.0200(2) Uani 1 1 d . . .
C11 C 0.7277(2) 0.60168(10) 0.44430(5) 0.0244(2) Uani 1 1 d . . .
C5 C 1.07849(18) 0.99792(10) 0.27685(5) 0.0208(2) Uani 1 1 d . . .
C14 C 0.38059(18) 0.72050(10) 0.28835(5) 0.0211(2) Uani 1 1 d . . .
C18 C 0.50936(19) 1.24958(10) 0.42674(4) 0.0219(2) Uani 1 1 d . . .
C9 C 0.99621(19) 0.77705(10) 0.44660(4) 0.0220(2) Uani 1 1 d . . .
C19 C 0.7011(2) 1.26983(10) 0.39368(4) 0.0222(2) Uani 1 1 d . . .
C17 C 0.45352(19) 1.12946(10) 0.44157(4) 0.0220(2) Uani 1 1 d . . .
C3 C 0.8650(2) 0.91930(10) 0.19272(4) 0.0232(2) Uani 1 1 d . . .
C10 C 0.9225(2) 0.66807(11) 0.47093(5) 0.0256(2) Uani 1 1 d . . .
H12 H 0.479(3) 0.5913(14) 0.3737(6) 0.028(4) Uiso 1 1 d . . .
H11 H 0.666(3) 0.5239(16) 0.4603(6) 0.034(4) Uiso 1 1 d . . .
H18 H 0.412(3) 1.3208(15) 0.4396(6) 0.034(4) Uiso 1 1 d . . .
H3 H 0.840(2) 0.9136(13) 0.1506(6) 0.023(3) Uiso 1 1 d . . .
H19 H 0.744(3) 1.3554(14) 0.3821(6) 0.024(3) Uiso 1 1 d . . .
H10 H 1.006(3) 0.6395(16) 0.5075(7) 0.036(4) Uiso 1 1 d . . .
H20 H 0.970(3) 1.1866(15) 0.3511(6) 0.033(4) Uiso 1 1 d . . .
H9 H 1.132(3) 0.8271(14) 0.4654(6) 0.024(3) Uiso 1 1 d . . .
H7 H 1.115(3) 0.9666(13) 0.3868(5) 0.024(3) Uiso 1 1 d . . .
H4 H 1.164(3) 1.0375(16) 0.1975(7) 0.040(4) Uiso 1 1 d . . .
H16 H 0.551(3) 0.9451(14) 0.4352(6) 0.029(4) Uiso 1 1 d . . .
H2 H 0.579(3) 0.7978(14) 0.2042(6) 0.026(3) Uiso 1 1 d . . .
H17 H 0.314(3) 1.1135(15) 0.4653(6) 0.030(4) Uiso 1 1 d . . .
H5 H 1.212(3) 1.0476(13) 0.2972(6) 0.026(3) Uiso 1 1 d . . .
H14A H 0.265(3) 0.7060(14) 0.3163(6) 0.030(4) Uiso 1 1 d . . .
H14B H 0.436(3) 0.6407(15) 0.2729(6) 0.031(4) Uiso 1 1 d . . .
H14C H 0.296(2) 0.7697(13) 0.2574(5) 0.020(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
N1 C13 1.4025(12) . ?
N1 C1 1.4056(13) . ?
N1 C14 1.4571(12) . ?
C13 C12 1.4029(14) . ?
C13 C8 1.4068(13) . ?
C15 C16 1.3939(14) . ?
C15 C20 1.3993(14) . ?
C15 C7 1.5339(13) . ?
C1 C2 1.4032(14) . ?
C1 C6 1.4077(13) . ?
C8 C9 1.3919(14) . ?
C8 C7 1.5044(14) . ?
C6 C5 1.3924(14) . ?
C6 C7 1.5124(14) . ?
C7 H7 1.013(14) . ?
C12 C11 1.3898(15) . ?
C12 H12 0.991(14) . ?
C16 C17 1.3949(14) . ?
C16 H16 0.985(15) . ?
C2 C3 1.3935(15) . ?
C2 H2 1.006(14) . ?
C4 C3 1.3865(16) . ?
C4 C5 1.3896(15) . ?
C4 H4 0.974(18) . ?
C20 C19 1.3896(15) . ?
C20 H20 1.004(16) . ?
C11 C10 1.3907(16) . ?
C11 H11 0.996(17) . ?
C5 H5 0.996(14) . ?
C14 H14A 0.977(16) . ?
C14 H14B 0.996(16) . ?
C14 H14C 0.992(13) . ?
C18 C17 1.3868(15) . ?
C18 C19 1.3934(15) . ?
C18 H18 1.003(16) . ?
C9 C10 1.3907(16) . ?
C9 H9 0.993(14) . ?
C19 H19 0.999(15) . ?
C17 H17 1.009(16) . ?
C3 H3 1.010(13) . ?
C10 H10 0.998(15) . ?

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 N1 C1 117.70(8) . . ?
C13 N1 C14 118.47(8) . . ?
C1 N1 C14 118.99(8) . . ?
N1 C13 C12 122.09(9) . . ?
N1 C13 C8 118.79(8) . . ?
C12 C13 C8 119.12(9) . . ?
C16 C15 C20 118.27(9) . . ?
C16 C15 C7 122.81(9) . . ?
C20 C15 C7 118.91(9) . . ?
C2 C1 N1 121.96(9) . . ?
C2 C1 C6 118.96(9) . . ?
N1 C1 C6 119.05(9) . . ?
C9 C8 C13 119.54(9) . . ?
C9 C8 C7 121.84(9) . . ?
C13 C8 C7 118.55(8) . . ?
C5 C6 C1 119.68(9) . . ?
C5 C6 C7 122.14(9) . . ?
C1 C6 C7 118.18(9) . . ?
C8 C7 C6 109.22(8) . . ?
C8 C7 C15 112.95(8) . . ?
C6 C7 C15 111.04(7) . . ?
C8 C7 H7 108.9(8) . . ?
C6 C7 H7 110.1(8) . . ?
C15 C7 H7 104.5(8) . . ?
C11 C12 C13 120.18(9) . . ?
C11 C12 H12 120.5(8) . . ?
C13 C12 H12 119.3(8) . . ?
C15 C16 C17 120.98(10) . . ?
C15 C16 H16 119.2(9) . . ?
C17 C16 H16 119.9(9) . . ?
C3 C2 C1 120.14(10) . . ?
C3 C2 H2 119.7(8) . . ?
C1 C2 H2 120.2(8) . . ?
C3 C4 C5 119.01(10) . . ?
C3 C4 H4 121.8(9) . . ?
C5 C4 H4 119.2(9) . . ?
C19 C20 C15 120.83(10) . . ?
C19 C20 H20 119.3(9) . . ?
C15 C20 H20 119.8(9) . . ?
C12 C11 C10 120.84(10) . . ?
C12 C11 H11 117.0(9) . . ?
C10 C11 H11 122.1(8) . . ?
C4 C5 C6 121.25(10) . . ?
C4 C5 H5 121.6(8) . . ?
C6 C5 H5 117.2(8) . . ?
N1 C14 H14A 107.3(9) . . ?
N1 C14 H14B 111.2(9) . . ?
H14A C14 H14B 110.8(13) . . ?
N1 C14 H14C 110.4(8) . . ?
H14A C14 H14C 108.4(12) . . ?
H14B C14 H14C 108.7(11) . . ?
C17 C18 C19 119.34(10) . . ?
C17 C18 H18 120.1(10) . . ?
C19 C18 H18 120.6(10) . . ?
C10 C9 C8 121.27(10) . . ?
C10 C9 H9 120.3(8) . . ?
C8 C9 H9 118.4(8) . . ?
C20 C19 C18 120.34(10) . . ?
C20 C19 H19 118.8(8) . . ?
C18 C19 H19 120.8(8) . . ?
C18 C17 C16 120.23(10) . . ?
C18 C17 H17 120.1(9) . . ?
C16 C17 H17 119.6(9) . . ?
C4 C3 C2 120.93(10) . . ?
C4 C3 H3 120.8(8) . . ?
C2 C3 H3 118.3(8) . . ?
C11 C10 C9 118.95(10) . . ?
C11 C10 H10 120.7(10) . . ?
C9 C10 H10 120.3(10) . . ?


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method ethanol
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_dc
_database_code_depnum_ccdc_archive 'CCDC 1479455'
_audit_update_record             
;
2016-05-12 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'9-(Furan-2-yl)-10-methyl-acridinium tetrafluoroborate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 B F4 N O'
_chemical_formula_sum            'C18 H14 B F4 N O'
_chemical_formula_weight         347.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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   P2(1)/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                   10.467(5)
_cell_length_b                   10.928(8)
_cell_length_c                   13.713(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.78(4)
_cell_angle_gamma                90.00
_cell_volume                     1545.7(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    931
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      26.39

_exptl_crystal_description       prismatic
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  -0.11980
_exptl_absorpt_correction_T_max  1.51831
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur 3 CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12228
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_sigmaI/netI    0.1735
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         26.39
_reflns_number_total             3151
_reflns_number_gt                931
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_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)+(0.0010P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3151
_refine_ls_number_parameters     263
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.1589
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.0417
_refine_ls_wR_factor_gt          0.0393
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.987
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1973(2) 0.02473(19) 0.41269(17) 0.0536(6) Uani 1 1 d . A 1
C8 C 0.1143(3) 0.1254(3) 0.5453(2) 0.0484(7) Uani 1 1 d . A 1
C6 C 0.0378(3) 0.1844(3) 0.37485(19) 0.0467(7) Uani 1 1 d . A 1
C2 C 0.1142(2) 0.0716(2) 0.2417(2) 0.0629(8) Uani 1 1 d . A 1
H2A H 0.1640 0.0092 0.2212 0.076 Uiso 1 1 calc R A 1
C13 C 0.1983(3) 0.0395(3) 0.5121(2) 0.0513(8) Uani 1 1 d . A 1
C1 C 0.1174(3) 0.0929(3) 0.3437(2) 0.0478(8) Uani 1 1 d . A 1
C7 C 0.0376(3) 0.2003(3) 0.47625(19) 0.0484(7) Uani 1 1 d . A 1
C9 C 0.1069(2) 0.1277(2) 0.6479(2) 0.0604(8) Uani 1 1 d . A 1
H9A H 0.0486 0.1802 0.6707 0.073 Uiso 1 1 calc R A 1
F4 F -0.55741(15) 0.18249(15) 0.46221(11) 0.1101(6) Uani 1 1 d . B 1
C14 C -0.0431(3) 0.2951(3) 0.5088(2) 0.0522(8) Uani 1 1 d D A 1
C4 C -0.0360(3) 0.2358(2) 0.2025(2) 0.0666(9) Uani 1 1 d . A 1
H4A H -0.0860 0.2846 0.1551 0.080 Uiso 1 1 calc R A 1
C10 C 0.1836(3) 0.0546(3) 0.71263(19) 0.0707(10) Uani 1 1 d . A 1
H10A H 0.1779 0.0572 0.7795 0.085 Uiso 1 1 calc R A 1
C3 C 0.0388(3) 0.1419(3) 0.17379(19) 0.0695(9) Uani 1 1 d . A 1
H3A H 0.0370 0.1270 0.1068 0.083 Uiso 1 1 calc R A 1
C5 C -0.0358(2) 0.2562(2) 0.3005(2) 0.0614(9) Uani 1 1 d . A 1
H5A H -0.0860 0.3197 0.3189 0.074 Uiso 1 1 calc R A 1
C12 C 0.2799(2) -0.0316(2) 0.5825(2) 0.0648(9) Uani 1 1 d . A 1
H12A H 0.3403 -0.0839 0.5619 0.078 Uiso 1 1 calc R A 1
C18 C 0.2860(2) -0.0652(2) 0.37787(16) 0.0819(9) Uani 1 1 d . A 1
H18A H 0.3441 -0.0976 0.4336 0.123 Uiso 1 1 calc R A 1
H18B H 0.3350 -0.0256 0.3338 0.123 Uiso 1 1 calc R A 1
H18C H 0.2361 -0.1307 0.3437 0.123 Uiso 1 1 calc R A 1
C11 C 0.2712(3) -0.0247(3) 0.6792(2) 0.0748(9) Uani 1 1 d . A 1
H11A H 0.3245 -0.0736 0.7244 0.090 Uiso 1 1 calc R A 1
F3 F -0.4688(5) 0.3400(6) 0.4010(5) 0.129(2) Uani 0.70 1 d P B 1
F2 F -0.6858(7) 0.3216(6) 0.3906(5) 0.157(3) Uani 0.70 1 d P B 1
B1 B -0.5728(6) 0.2676(4) 0.3891(3) 0.0633(12) Uani 1 1 d . B 1
C16 C -0.1995(3) 0.4236(3) 0.5292(3) 0.0853(11) Uani 1 1 d . A 1
H16A H -0.2779 0.4639 0.5286 0.102 Uiso 1 1 calc R A 1
C17 C -0.0954(4) 0.4481(3) 0.5948(2) 0.0920(12) Uani 1 1 d D A 1
H17A H -0.0917 0.5093 0.6424 0.110 Uiso 1 1 calc R A 1
F1 F -0.5773(6) 0.2036(4) 0.3031(3) 0.151(2) Uani 0.70 1 d P B 1
C15 C -0.183(3) 0.329(3) 0.4573(18) 0.067(3) Uani 0.50 1 d P A 1
H15A H -0.2369 0.2992 0.4012 0.081 Uiso 0.50 1 calc PR A 1
O1 O 0.008(3) 0.372(3) 0.585(2) 0.062(3) Uani 0.50 1 d P A 1
H15B H 0.063(4) 0.357(4) 0.635(3) 0.075 Uiso 0.50 1 d P C 2
F3A F -0.4919(11) 0.2430(11) 0.3235(8) 0.117(4) Uani 0.30 1 d PU D 2
F2A F -0.5284(13) 0.3778(12) 0.4282(8) 0.104(4) Uani 0.30 1 d PU E 2
F1A F -0.6810(13) 0.2903(12) 0.3385(8) 0.096(4) Uani 0.30 1 d PU F 2
O1A O -0.1586(16) 0.3200(16) 0.4795(10) 0.067(3) Uani 0.50 1 d P G 2
C15A C -0.007(4) 0.366(5) 0.586(4) 0.062(3) Uani 0.50 1 d PD H 2


_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
N1 C1 1.372(2) . ?
N1 C13 1.371(2) . ?
N1 C18 1.485(2) . ?
C8 C7 1.398(3) . ?
C8 C13 1.413(3) . ?
C8 C9 1.421(3) . ?
C6 C7 1.402(3) . ?
C6 C1 1.413(3) . ?
C6 C5 1.408(3) . ?
C2 C3 1.353(3) . ?
C2 C1 1.412(3) . ?
C2 H2A 0.9300 . ?
C13 C12 1.409(3) . ?
C7 C14 1.453(3) . ?
C9 C10 1.352(3) . ?
C9 H9A 0.9300 . ?
F4 B1 1.357(4) . ?
C14 C15 1.56(3) . ?
C14 O1 1.377(15) . ?
C4 C5 1.361(3) . ?
C4 C3 1.388(3) . ?
C4 H4A 0.9300 . ?
C10 C11 1.394(3) . ?
C10 H10A 0.9300 . ?
C3 H3A 0.9300 . ?
C5 H5A 0.9300 . ?
C12 C11 1.347(3) . ?
C12 H12A 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C11 H11A 0.9300 . ?
F3 B1 1.334(7) . ?
F2 B1 1.325(7) . ?
B1 F1 1.365(6) . ?
C16 C17 1.317(3) . ?
C16 C15 1.46(3) . ?
C16 H16A 0.9300 . ?
C17 O1 1.387(15) . ?
C17 C15 2.35(3) . ?
C17 H17A 0.9300 . ?
C15 H15A 0.9300 . ?
O1 H15B 0.83(4) . ?
C15A H15B 0.90(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
C1 N1 C13 121.5(2) . . ?
C1 N1 C18 118.6(2) . . ?
C13 N1 C18 119.9(3) . . ?
C7 C8 C13 119.2(3) . . ?
C7 C8 C9 122.6(3) . . ?
C13 C8 C9 118.2(3) . . ?
C7 C6 C1 119.2(3) . . ?
C7 C6 C5 123.8(3) . . ?
C1 C6 C5 116.9(2) . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
N1 C13 C12 121.1(3) . . ?
N1 C13 C8 119.9(3) . . ?
C12 C13 C8 118.9(3) . . ?
N1 C1 C2 120.2(3) . . ?
N1 C1 C6 119.8(3) . . ?
C2 C1 C6 120.0(3) . . ?
C8 C7 C6 120.2(3) . . ?
C8 C7 C14 120.4(3) . . ?
C6 C7 C14 119.4(3) . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9A 119.6 . . ?
C8 C9 H9A 119.6 . . ?
C15 C14 O1 114.3(13) . . ?
C15 C14 C7 125.4(11) . . ?
O1 C14 C7 119.9(7) . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
C9 C10 C11 120.1(3) . . ?
C9 C10 H10A 120.0 . . ?
C11 C10 H10A 120.0 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C4 C5 C6 122.2(3) . . ?
C4 C5 H5A 118.9 . . ?
C6 C5 H5A 118.9 . . ?
C11 C12 C13 120.5(3) . . ?
C11 C12 H12A 119.7 . . ?
C13 C12 H12A 119.7 . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11A 119.4 . . ?
C10 C11 H11A 119.4 . . ?
F3 B1 F2 116.5(6) . . ?
F3 B1 F1 108.5(5) . . ?
F2 B1 F1 110.0(5) . . ?
F3 B1 F4 108.9(4) . . ?
F2 B1 F4 106.7(5) . . ?
F1 B1 F4 105.6(4) . . ?
C17 C16 C15 115.3(11) . . ?
C17 C16 H16A 122.3 . . ?
C15 C16 H16A 122.3 . . ?
C16 C17 O1 112.3(7) . . ?
C16 C17 C15 34.2(7) . . ?
O1 C17 C15 78.1(9) . . ?
C16 C17 H17A 123.9 . . ?
O1 C17 H17A 123.9 . . ?
C15 C17 H17A 157.9 . . ?
C14 C15 C16 94.0(16) . . ?
C14 C15 C17 63.8(10) . . ?
C16 C15 C17 30.5(6) . . ?
C14 C15 H15A 133.0 . . ?
C16 C15 H15A 133.0 . . ?
C17 C15 H15A 163.0 . . ?
C14 O1 C17 103.5(12) . . ?
C14 O1 H15B 129(4) . . ?
C17 O1 H15B 118(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.39
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.033

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method water
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_144
_database_code_depnum_ccdc_archive 'CCDC 1479456'
_audit_update_record             
;
2016-05-12 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;
_chemical_formula_moiety         'C20 H18 N2'
_chemical_formula_sum            'C20 H18 N2'
_chemical_formula_weight         286.38
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_cell_length_a                   8.4601(3)
_cell_length_b                   10.9097(5)
_cell_length_c                   16.1704(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.110(3)
_cell_angle_gamma                90
_cell_volume                     1488.65(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6286
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      30.78
_cell_measurement_temperature    150(2)
_exptl_absorpt_coefficient_mu    0.075
_exptl_crystal_density_diffrn    1.2777
_exptl_crystal_F_000             608.2190
_exptl_crystal_description       prism
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6286
_diffrn_reflns_theta_max         30.7834
_diffrn_measured_fraction_theta_max 0.8792
_diffrn_reflns_theta_full        28.2205
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_reflns_theta_min         2.25
_diffrn_ambient_temperature      150(2)
_diffrn_measurement_device_type  'Xcalibur 3'


_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                2779
_reflns_number_total             3487
_reflns_threshold_expression     I>=2u(I)
_refine_diff_density_max         0.288803
_refine_diff_density_min         -0.255237
_refine_diff_density_rms         0.055339
_refine_ls_d_res_high            0.693946
_refine_ls_d_res_low             9.041727
_refine_ls_goodness_of_fit_ref   1.055446
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     270
_refine_ls_number_reflns         3487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.058199
_refine_ls_R_factor_gt           0.044044
_refine_ls_restrained_S_all      1.055446
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0750P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.133602
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
N1 N 0.86253(12) -0.04046(9) 0.36743(6) 0.0264(2) Uani 1 1 d . . .
C13 C 1.01877(13) 0.00395(11) 0.37246(7) 0.0247(2) Uani 1 1 d . . .
C16 C 0.75539(13) 0.26835(11) 0.41535(7) 0.0223(2) Uani 1 1 d . . .
C4 C 0.53846(15) 0.08740(13) 0.17711(8) 0.0323(3) Uani 1 1 d . . .
C1 C 0.75522(13) 0.00069(10) 0.30329(7) 0.0223(2) Uani 1 1 d . . .
N2 N 0.71863(15) 0.57019(11) 0.51715(8) 0.0349(3) Uani 1 1 d . . .
C19 C 0.88542(15) 0.50007(11) 0.41033(8) 0.0285(3) Uani 1 1 d . . .
C6 C 0.78000(13) 0.11423(10) 0.26582(7) 0.0214(2) Uani 1 1 d . . .
C17 C 0.70887(14) 0.35837(11) 0.46907(7) 0.0250(2) Uani 1 1 d . . .
C3 C 0.51457(15) -0.02500(13) 0.21391(8) 0.0319(3) Uani 1 1 d . . .
C7 C 0.91705(13) 0.19468(10) 0.29713(7) 0.0214(2) Uani 1 1 d . . .
C5 C 0.67199(14) 0.15556(12) 0.20299(7) 0.0273(3) Uani 1 1 d . . .
C9 C 1.20656(14) 0.16004(13) 0.33975(8) 0.0314(3) Uani 1 1 d . . .
C12 C 1.14405(16) -0.06333(13) 0.41208(8) 0.0339(3) Uani 1 1 d . . .
C11 C 1.29676(17) -0.01801(15) 0.41569(10) 0.0406(4) Uani 1 1 d . . .
C20 C 0.93011(14) 0.41000(11) 0.35606(8) 0.0257(3) Uani 1 1 d . . .
C18 C 0.77267(14) 0.47626(11) 0.46709(7) 0.0258(3) Uani 1 1 d . . .
C15 C 0.86570(12) 0.29237(10) 0.35731(7) 0.0200(2) Uani 1 1 d . . .
C8 C 1.05132(13) 0.11748(11) 0.33646(7) 0.0230(2) Uani 1 1 d . . .
C2 C 0.62170(15) -0.06925(12) 0.27577(8) 0.0281(3) Uani 1 1 d . . .
C10 C 1.32991(15) 0.09337(15) 0.37943(9) 0.0400(4) Uani 1 1 d . . .
C14 C 0.82391(18) -0.14998(12) 0.41310(9) 0.0349(3) Uani 1 1 d . . .
H4 H 0.4613(17) 0.1172(14) 0.1324(9) 0.035(4) Uiso 1 1 d . . .
H3 H 0.4225(19) -0.0753(15) 0.1949(10) 0.039(4) Uiso 1 1 d . . .
H5 H 0.6891(17) 0.2360(15) 0.1769(10) 0.038(4) Uiso 1 1 d . . .
H17 H 0.6282(18) 0.3426(14) 0.5070(10) 0.037(4) Uiso 1 1 d . . .
H2 H 0.6067(18) -0.1499(16) 0.3013(10) 0.044(4) Uiso 1 1 d . . .
H14A H 0.844(2) -0.2274(17) 0.3808(11) 0.052(5) Uiso 1 1 d . . .
H20 H 1.0113(18) 0.4257(15) 0.3163(10) 0.035(4) Uiso 1 1 d . . .
H7 H 0.9578(16) 0.2414(14) 0.2479(9) 0.029(4) Uiso 1 1 d . . .
H14B H 0.7076(19) -0.1460(15) 0.4241(10) 0.041(4) Uiso 1 1 d . . .
H16 H 0.7074(16) 0.1860(14) 0.4176(9) 0.028(4) Uiso 1 1 d . . .
H9 H 1.2272(18) 0.2407(15) 0.3135(9) 0.038(4) Uiso 1 1 d . . .
H19 H 0.9331(19) 0.5828(15) 0.4079(10) 0.041(4) Uiso 1 1 d . . .
H11 H 1.384(2) -0.0655(17) 0.4425(12) 0.057(5) Uiso 1 1 d . . .
H14C H 0.8901(18) -0.1527(14) 0.4660(10) 0.035(4) Uiso 1 1 d . . .
H10 H 1.441(2) 0.1267(16) 0.3782(10) 0.045(4) Uiso 1 1 d . . .
H12 H 1.123(2) -0.1456(17) 0.4366(11) 0.049(5) Uiso 1 1 d . . .
H2A H 0.665(2) 0.5430(18) 0.5630(13) 0.061(6) Uiso 1 1 d . . .
H2B H 0.796(2) 0.6244(19) 0.5316(12) 0.061(6) 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
N1 C1 1.4023(15) . ?
N1 C13 1.4044(15) . ?
N1 C14 1.4544(16) . ?
C13 C8 1.4046(17) . ?
C13 C12 1.4053(17) . ?
C16 C17 1.3870(16) . ?
C16 C15 1.3950(16) . ?
C16 H16 0.988(15) . ?
C4 C3 1.384(2) . ?
C4 C5 1.3915(17) . ?
C4 H4 0.993(15) . ?
C1 C6 1.4016(16) . ?
C1 C2 1.4086(16) . ?
N2 C18 1.4029(16) . ?
N2 H2A 0.95(2) . ?
N2 H2B 0.90(2) . ?
C19 C20 1.3882(17) . ?
C19 C18 1.3947(18) . ?
C19 H19 0.991(17) . ?
C6 C5 1.3918(16) . ?
C6 C7 1.5121(15) . ?
C17 C18 1.3963(17) . ?
C17 H17 0.966(16) . ?
C3 C2 1.3874(18) . ?
C3 H3 0.984(16) . ?
C7 C8 1.5167(15) . ?
C7 C15 1.5275(16) . ?
C7 H7 1.025(15) . ?
C5 H5 0.989(17) . ?
C9 C8 1.3902(16) . ?
C9 C10 1.3904(19) . ?
C9 H9 0.998(16) . ?
C12 C11 1.380(2) . ?
C12 H12 1.003(18) . ?
C11 C10 1.387(2) . ?
C11 H11 0.977(19) . ?
C20 C15 1.3952(16) . ?
C20 H20 0.989(16) . ?
C2 H2 0.984(17) . ?
C10 H10 1.009(17) . ?
C14 H14A 1.015(19) . ?
C14 H14B 1.013(16) . ?
C14 H14C 0.989(15) . ?

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 C13 119.26(10) . . ?
C1 N1 C14 118.80(10) . . ?
C13 N1 C14 119.93(10) . . ?
N1 C13 C8 119.47(10) . . ?
N1 C13 C12 121.45(12) . . ?
C8 C13 C12 119.08(11) . . ?
C17 C16 C15 121.46(11) . . ?
C17 C16 H16 119.1(8) . . ?
C15 C16 H16 119.4(8) . . ?
C3 C4 C5 118.99(11) . . ?
C3 C4 H4 119.6(9) . . ?
C5 C4 H4 121.4(9) . . ?
C6 C1 N1 119.60(10) . . ?
C6 C1 C2 118.93(10) . . ?
N1 C1 C2 121.46(11) . . ?
C18 N2 H2A 114.7(12) . . ?
C18 N2 H2B 111.8(12) . . ?
H2A N2 H2B 112.6(17) . . ?
C20 C19 C18 120.95(11) . . ?
C20 C19 H19 119.3(10) . . ?
C18 C19 H19 119.7(10) . . ?
C5 C6 C1 119.43(10) . . ?
C5 C6 C7 120.23(10) . . ?
C1 C6 C7 120.22(10) . . ?
C16 C17 C18 120.71(11) . . ?
C16 C17 H17 121.2(9) . . ?
C18 C17 H17 118.1(9) . . ?
C4 C3 C2 120.69(11) . . ?
C4 C3 H3 119.8(9) . . ?
C2 C3 H3 119.5(9) . . ?
C6 C7 C8 110.54(9) . . ?
C6 C7 C15 111.86(9) . . ?
C8 C7 C15 111.04(9) . . ?
C6 C7 H7 108.7(8) . . ?
C8 C7 H7 108.6(8) . . ?
C15 C7 H7 105.9(8) . . ?
C4 C5 C6 121.50(12) . . ?
C4 C5 H5 119.1(8) . . ?
C6 C5 H5 119.4(9) . . ?
C8 C9 C10 121.22(14) . . ?
C8 C9 H9 118.2(9) . . ?
C10 C9 H9 120.6(9) . . ?
C11 C12 C13 120.31(14) . . ?
C11 C12 H12 119.7(10) . . ?
C13 C12 H12 120.0(10) . . ?
C12 C11 C10 120.87(13) . . ?
C12 C11 H11 120.1(11) . . ?
C10 C11 H11 119.0(11) . . ?
C19 C20 C15 121.19(11) . . ?
C19 C20 H20 121.5(9) . . ?
C15 C20 H20 117.3(9) . . ?
C19 C18 C17 118.06(11) . . ?
C19 C18 N2 120.68(12) . . ?
C17 C18 N2 121.16(12) . . ?
C16 C15 C20 117.60(11) . . ?
C16 C15 C7 122.15(10) . . ?
C20 C15 C7 120.25(10) . . ?
C9 C8 C13 119.44(11) . . ?
C9 C8 C7 120.48(11) . . ?
C13 C8 C7 120.04(10) . . ?
C3 C2 C1 120.44(12) . . ?
C3 C2 H2 121.1(9) . . ?
C1 C2 H2 118.5(9) . . ?
C11 C10 C9 119.07(13) . . ?
C11 C10 H10 122.8(10) . . ?
C9 C10 H10 118.1(10) . . ?
N1 C14 H14A 111.7(10) . . ?
N1 C14 H14B 108.1(9) . . ?
H14A C14 H14B 109.2(14) . . ?
N1 C14 H14C 109.3(9) . . ?
H14A C14 H14C 108.3(13) . . ?
H14B C14 H14C 110.3(13) . . ?


_chemical_name_systematic        
10-Methyl-9-(4-aminophenyl)-9,10-dihydroacridine
_exptl_crystal_colour            Colorless
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method ethanol
