# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_2a
_audit_block_doi                 10.5517/cc13xm1p
_database_code_depnum_ccdc_archive 'CCDC 1040392'
_audit_update_record             
;
2014-12-19 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;

_audit_creation_date             2014-09-24
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 N'
_chemical_formula_sum            'C22 H19 N'
_chemical_formula_weight         297.38
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.4941(2)
_cell_length_b                   24.8448(10)
_cell_length_c                   12.4135(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.044(4)
_cell_angle_gamma                90
_cell_volume                     1657.15(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3105
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.4370
_cell_measurement_theta_min      1.8510
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.192
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11019
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.864
_diffrn_reflns_theta_min         1.867
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 16.15
_diffrn_detector_type            'Sapphire3 CCD area detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    0.90   27.00   0.3000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0936 -100.0000 -120.0000 87

#__ type_ start__ end____ width___ exp.time_
  2 omega  -85.00   36.20   0.3000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0936    0.0000 -150.0000 404

#__ type_ start__ end____ width___ exp.time_
  3 omega   -5.00   88.00   0.3000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7186   57.0000   90.0000 310

#__ type_ start__ end____ width___ exp.time_
  4 omega   35.00   71.90   0.3000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7186  178.0000  -30.0000 123

#__ type_ start__ end____ width___ exp.time_
  5 omega  -54.00   51.00   0.3000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7186  -77.0000  -30.0000 350
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0126136000
_diffrn_orient_matrix_UB_12      0.0259044000
_diffrn_orient_matrix_UB_13      0.0245566000
_diffrn_orient_matrix_UB_21      -0.0312755000
_diffrn_orient_matrix_UB_22      -0.0107906000
_diffrn_orient_matrix_UB_23      0.0482388000
_diffrn_orient_matrix_UB_31      0.1276156000
_diffrn_orient_matrix_UB_32      -0.0052200000
_diffrn_orient_matrix_UB_33      0.0220648000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2917
_reflns_number_total             3426
_reflns_odcompleteness_completeness 99.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.01
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  
'SHELXL 2014/3 multi-CPU version (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3426
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+0.5130P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0961
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2), C3(H3), C16(H16), C13(H13), C21(H21), C14(H14), C12(H12),
 C6(H6), C7(H7), C19(H19), C9(H9), C10(H10), C8(H8), C22(H22), C15(H15),
 C18(H18), C20(H20)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N 0.28259(19) 0.39834(4) 0.17878(8) 0.0220(2) Uani 1 1 d . . . . .
C11 C 0.3333(2) 0.40284(5) 0.37662(9) 0.0199(3) Uani 1 1 d . . . . .
C4 C 0.6747(2) 0.35258(5) -0.00124(10) 0.0238(3) Uani 1 1 d . . . . .
H4 H 0.8016 0.3773 0.0229 0.029 Uiso 1 1 calc R . . . .
C2 C 0.4719(2) 0.39284(5) 0.13550(9) 0.0215(3) Uani 1 1 d . . . . .
H2 H 0.6109 0.4142 0.1613 0.026 Uiso 1 1 calc R . . . .
C5 C 0.7106(2) 0.31558(5) -0.08886(10) 0.0212(3) Uani 1 1 d . . . . .
C3 C 0.4803(2) 0.35470(5) 0.04752(9) 0.0222(3) Uani 1 1 d . . . . .
H3 H 0.3474 0.3313 0.0248 0.027 Uiso 1 1 calc R . . . .
C1 C 0.3117(2) 0.43613(5) 0.27232(9) 0.0206(3) Uani 1 1 d . . . . .
H1 H 0.4679 0.4559 0.2768 0.025 Uiso 1 1 calc R . . . .
C16 C 0.5476(2) 0.40540(5) 0.45867(10) 0.0241(3) Uani 1 1 d . . . . .
H16 H 0.6750 0.4288 0.4509 0.029 Uiso 1 1 calc R . . . .
C13 C 0.1704(2) 0.33549(5) 0.48289(11) 0.0260(3) Uani 1 1 d . . . . .
H13 H 0.0436 0.3120 0.4908 0.031 Uiso 1 1 calc R . . . .
C21 C -0.1509(3) 0.54116(5) 0.33000(11) 0.0289(3) Uani 1 1 d . . . . .
H21 H -0.1913 0.5580 0.3908 0.035 Uiso 1 1 calc R . . . .
C14 C 0.3857(2) 0.33834(5) 0.56414(10) 0.0274(3) Uani 1 1 d . . . . .
H14 H 0.4034 0.3167 0.6264 0.033 Uiso 1 1 calc R . . . .
C12 C 0.1442(2) 0.36767(5) 0.38979(10) 0.0230(3) Uani 1 1 d . . . . .
H12 H -0.0009 0.3657 0.3357 0.028 Uiso 1 1 calc R . . . .
C17 C 0.0993(2) 0.47671(5) 0.25504(10) 0.0208(3) Uani 1 1 d . . . . .
C6 C 0.5732(2) 0.26821(5) -0.11352(10) 0.0257(3) Uani 1 1 d . . . . .
H6 H 0.4516 0.2596 -0.0743 0.031 Uiso 1 1 calc R . . . .
C7 C 0.6158(3) 0.23403(5) -0.19529(11) 0.0305(3) Uani 1 1 d . . . . .
H7 H 0.5219 0.2028 -0.2111 0.037 Uiso 1 1 calc R . . . .
C19 C -0.2129(3) 0.52976(5) 0.13481(11) 0.0307(3) Uani 1 1 d . . . . .
H19 H -0.2959 0.5388 0.0639 0.037 Uiso 1 1 calc R . . . .
C9 C 0.9351(2) 0.29269(6) -0.23081(11) 0.0289(3) Uani 1 1 d . . . . .
H9 H 1.0567 0.3010 -0.2702 0.035 Uiso 1 1 calc R . . . .
C10 C 0.8925(2) 0.32723(5) -0.14910(10) 0.0255(3) Uani 1 1 d . . . . .
H10 H 0.9862 0.3585 -0.1341 0.031 Uiso 1 1 calc R . . . .
C8 C 0.7981(3) 0.24605(6) -0.25406(11) 0.0302(3) Uani 1 1 d . . . . .
H8 H 0.8276 0.2228 -0.3087 0.036 Uiso 1 1 calc R . . . .
C22 C 0.0344(2) 0.50245(5) 0.34474(10) 0.0249(3) Uani 1 1 d . . . . .
H22 H 0.1169 0.4935 0.4157 0.030 Uiso 1 1 calc R . . . .
C15 C 0.5741(2) 0.37340(6) 0.55236(10) 0.0278(3) Uani 1 1 d . . . . .
H15 H 0.7181 0.3756 0.6070 0.033 Uiso 1 1 calc R . . . .
C18 C -0.0264(2) 0.49123(5) 0.14987(10) 0.0262(3) Uani 1 1 d . . . . .
H18 H 0.0153 0.4749 0.0888 0.031 Uiso 1 1 calc R . . . .
C20 C -0.2764(3) 0.55488(5) 0.22474(11) 0.0295(3) Uani 1 1 d . . . . .
H20 H -0.4018 0.5807 0.2146 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
N C2 1.2737(15) . ?
N C1 1.4757(15) . ?
C11 C1 1.5200(16) . ?
C11 C16 1.3882(17) . ?
C11 C12 1.3932(17) . ?
C4 C5 1.4684(17) . ?
C4 C3 1.3343(17) . ?
C2 C3 1.4538(16) . ?
C5 C6 1.3969(18) . ?
C5 C10 1.3981(17) . ?
C1 C17 1.5231(17) . ?
C16 C15 1.3912(17) . ?
C13 C14 1.3867(19) . ?
C13 C12 1.3878(17) . ?
C21 C22 1.3847(18) . ?
C21 C20 1.3866(19) . ?
C14 C15 1.3838(19) . ?
C17 C22 1.3936(17) . ?
C17 C18 1.3911(17) . ?
C6 C7 1.3803(18) . ?
C7 C8 1.3893(19) . ?
C19 C18 1.3861(19) . ?
C19 C20 1.3856(19) . ?
C9 C10 1.3851(18) . ?
C9 C8 1.379(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N C1 115.86(10) . . ?
C16 C11 C1 120.23(11) . . ?
C16 C11 C12 118.80(11) . . ?
C12 C11 C1 120.91(11) . . ?
C3 C4 C5 127.19(12) . . ?
N C2 C3 122.92(11) . . ?
C6 C5 C4 122.68(11) . . ?
C6 C5 C10 118.10(11) . . ?
C10 C5 C4 119.20(11) . . ?
C4 C3 C2 121.35(12) . . ?
N C1 C11 107.49(9) . . ?
N C1 C17 110.87(9) . . ?
C11 C1 C17 113.67(9) . . ?
C11 C16 C15 120.79(12) . . ?
C14 C13 C12 120.06(12) . . ?
C22 C21 C20 120.17(12) . . ?
C15 C14 C13 119.90(12) . . ?
C13 C12 C11 120.57(12) . . ?
C22 C17 C1 120.51(11) . . ?
C18 C17 C1 121.31(11) . . ?
C18 C17 C22 118.10(12) . . ?
C7 C6 C5 120.86(12) . . ?
C6 C7 C8 120.34(13) . . ?
C20 C19 C18 120.38(12) . . ?
C8 C9 C10 120.38(12) . . ?
C9 C10 C5 120.81(12) . . ?
C9 C8 C7 119.50(12) . . ?
C21 C22 C17 121.13(12) . . ?
C14 C15 C16 119.87(12) . . ?
C19 C18 C17 120.93(12) . . ?
C19 C20 C21 119.29(12) . . ?

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
N C2 C3 C4 175.25(12) . . . . ?
N C1 C17 C22 156.10(11) . . . . ?
N C1 C17 C18 -27.26(15) . . . . ?
C11 C1 C17 C22 34.87(15) . . . . ?
C11 C1 C17 C18 -148.48(11) . . . . ?
C11 C16 C15 C14 0.29(19) . . . . ?
C4 C5 C6 C7 -178.85(12) . . . . ?
C4 C5 C10 C9 178.67(11) . . . . ?
C2 N C1 C11 -106.54(12) . . . . ?
C2 N C1 C17 128.66(11) . . . . ?
C5 C4 C3 C2 178.55(11) . . . . ?
C5 C6 C7 C8 0.5(2) . . . . ?
C3 C4 C5 C6 -17.1(2) . . . . ?
C3 C4 C5 C10 164.24(12) . . . . ?
C1 N C2 C3 175.88(10) . . . . ?
C1 C11 C16 C15 -177.18(11) . . . . ?
C1 C11 C12 C13 176.85(11) . . . . ?
C1 C17 C22 C21 177.12(11) . . . . ?
C1 C17 C18 C19 -177.45(11) . . . . ?
C16 C11 C1 N 118.35(12) . . . . ?
C16 C11 C1 C17 -118.56(12) . . . . ?
C16 C11 C12 C13 -0.48(18) . . . . ?
C13 C14 C15 C16 -0.44(19) . . . . ?
C14 C13 C12 C11 0.33(18) . . . . ?
C12 C11 C1 N -58.94(14) . . . . ?
C12 C11 C1 C17 64.15(14) . . . . ?
C12 C11 C16 C15 0.17(18) . . . . ?
C12 C13 C14 C15 0.14(19) . . . . ?
C6 C5 C10 C9 -0.03(18) . . . . ?
C6 C7 C8 C9 -0.6(2) . . . . ?
C10 C5 C6 C7 -0.20(18) . . . . ?
C10 C9 C8 C7 0.4(2) . . . . ?
C8 C9 C10 C5 -0.1(2) . . . . ?
C22 C21 C20 C19 -0.5(2) . . . . ?
C22 C17 C18 C19 -0.73(18) . . . . ?
C18 C17 C22 C21 0.37(18) . . . . ?
C18 C19 C20 C21 0.1(2) . . . . ?
C20 C21 C22 C17 0.23(19) . . . . ?
C20 C19 C18 C17 0.5(2) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
####################################################################### 
# 
# 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_2b
_audit_block_doi                 10.5517/cc13xm2q
_database_code_depnum_ccdc_archive 'CCDC 1040393'
_audit_update_record             
;
2014-12-19 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;

_audit_creation_date             2014-10-27
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.10.22 svn.r3046 for OlexSys, GUI svn.r4928)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 N O'
_chemical_formula_sum            'C23 H21 N O'
_chemical_formula_weight         327.41
_chemical_melting_point          ?

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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1174(4)
_cell_length_b                   11.8050(4)
_cell_length_c                   12.9211(4)
_cell_angle_alpha                89.082(3)
_cell_angle_beta                 80.227(5)
_cell_angle_gamma                76.501(5)
_cell_volume                     893.89(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7879
_cell_measurement_temperature    120
_cell_measurement_theta_max      31.7250
_cell_measurement_theta_min      1.7830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.8623
_exptl_absorpt_correction_T_min  0.6608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2009/1 (Bruker,2010) was used for absorption correction. 
wR2(int) was 0.0954 before and 0.0689 after correction. The Ratio 
of minimum to maximum transmission is 0.7663. The λ/2 correction 
factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       lathe
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.7739
_exptl_crystal_size_mid          0.2708
_exptl_crystal_size_min          0.0951
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29862
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.306
_diffrn_reflns_theta_min         1.600
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.15
_diffrn_detector_type            'Sapphire3 CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -3.00   94.20   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133   77.0000 -120.0000 324

#__ type_ start__ end____ width___ exp.time_
  2 omega   35.00   98.00   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133  178.0000   60.0000 210

#__ type_ start__ end____ width___ exp.time_
  3 omega   -3.00   94.20   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133   77.0000  150.0000 324

#__ type_ start__ end____ width___ exp.time_
  4 omega  -44.00   53.20   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133  -77.0000  -60.0000 324

#__ type_ start__ end____ width___ exp.time_
  5 omega   -3.00   94.20   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133   77.0000   60.0000 324

#__ type_ start__ end____ width___ exp.time_
  6 omega  -44.00   53.20   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133  -77.0000   30.0000 324

#__ type_ start__ end____ width___ exp.time_
  7 omega  -88.00   -7.00   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -24.7883  139.0000   97.0000 270

#__ type_ start__ end____ width___ exp.time_
  8 omega  -43.00   44.00   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -24.7883   57.0000 -180.0000 290

#__ type_ start__ end____ width___ exp.time_
  9 omega   35.00   98.00   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133  178.0000 -150.0000 210

#__ type_ start__ end____ width___ exp.time_
 10 omega   35.00   98.00   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133  178.0000  -30.0000 210

#__ type_ start__ end____ width___ exp.time_
 11 omega    7.00   94.00   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133   57.0000   30.0000 290

#__ type_ start__ end____ width___ exp.time_
 12 omega    7.00   94.00   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133   57.0000  -30.0000 290

#__ type_ start__ end____ width___ exp.time_
 13 omega  -47.00   46.00   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -24.7883   38.0000  120.0000 310

#__ type_ start__ end____ width___ exp.time_
 14 omega  -95.00   -3.80   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -24.7883  -38.0000   30.0000 304

#__ type_ start__ end____ width___ exp.time_
 15 omega  -24.00   66.00   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133 -100.0000   60.0000 300

#__ type_ start__ end____ width___ exp.time_
 16 omega   -3.00   19.50   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133   77.0000  -60.0000 75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies, Gemini S Ultra kappa-diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0134251000
_diffrn_orient_matrix_UB_12      0.0566722000
_diffrn_orient_matrix_UB_13      0.0213650000
_diffrn_orient_matrix_UB_21      -0.0186445000
_diffrn_orient_matrix_UB_22      -0.0217010000
_diffrn_orient_matrix_UB_23      0.0514549000
_diffrn_orient_matrix_UB_31      0.1188190000
_diffrn_orient_matrix_UB_32      -0.0117421000
_diffrn_orient_matrix_UB_33      0.0007980000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4775
_reflns_number_total             5955
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 
(release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 
2014,18:38:05)
;
_computing_data_collection       
; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 
(release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 
2014,18:38:05)
;
_computing_data_reduction        
; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 
(release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 
2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  
'SHELXL 2014/7 multi-CPU version (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         5955
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0680P)²+0.2220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1452
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C6(H6), C7(H7), C2(H2), C12(H12), C10(H10), C9(H9), C13(H13),
 C14(H14), C15(H15), C16(H16), C21(H21), C22(H22), C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O -0.32672(14) 0.54940(8) 0.78516(6) 0.03179(19) Uani 1 1 d . . . . .
N N 0.83452(16) 0.19807(8) 0.29608(7) 0.02697(19) Uani 1 1 d . . . . .
C5 C 0.12953(18) 0.34018(9) 0.54784(8) 0.0249(2) Uani 1 1 d . . . . .
C4 C 0.28270(19) 0.26915(10) 0.46164(8) 0.0273(2) Uani 1 1 d . . . . .
H4 H 0.2248 0.2117 0.4317 0.033 Uiso 1 1 calc R . . . .
C3 C 0.49558(18) 0.27548(9) 0.41970(8) 0.0263(2) Uani 1 1 d . . . . .
H3 H 0.5615 0.3313 0.4472 0.032 Uiso 1 1 calc R . . . .
C1 C 0.94332(18) 0.11726(9) 0.20666(8) 0.0248(2) Uani 1 1 d . . . . .
H1 H 0.8369 0.0672 0.1966 0.030 Uiso 1 1 calc R . . . .
C6 C 0.17137(18) 0.44140(10) 0.58808(8) 0.0260(2) Uani 1 1 d . . . . .
H6 H 0.3091 0.4638 0.5610 0.031 Uiso 1 1 calc R . . . .
C7 C 0.01648(18) 0.50893(10) 0.66616(8) 0.0268(2) Uani 1 1 d . . . . .
H7 H 0.0472 0.5776 0.6917 0.032 Uiso 1 1 calc R . . . .
C2 C 0.62685(18) 0.19876(9) 0.33323(8) 0.0262(2) Uani 1 1 d . . . . .
H2 H 0.5558 0.1471 0.3030 0.031 Uiso 1 1 calc R . . . .
C12 C 1.11194(18) 0.26903(9) 0.10308(8) 0.0265(2) Uani 1 1 d . . . . .
H12 H 1.1941 0.2748 0.1581 0.032 Uiso 1 1 calc R . . . .
C8 C -0.18607(18) 0.47659(10) 0.70798(8) 0.0255(2) Uani 1 1 d . . . . .
C10 C -0.07363(19) 0.30997(10) 0.59051(8) 0.0282(2) Uani 1 1 d . . . . .
H10 H -0.1057 0.2420 0.5643 0.034 Uiso 1 1 calc R . . . .
C9 C -0.23127(19) 0.37625(10) 0.67043(8) 0.0287(2) Uani 1 1 d . . . . .
H9 H -0.3675 0.3532 0.6988 0.034 Uiso 1 1 calc R . . . .
C11 C 0.97459(17) 0.18929(9) 0.10925(8) 0.0243(2) Uani 1 1 d . . . . .
C17 C 1.16455(18) 0.03818(9) 0.22961(8) 0.0259(2) Uani 1 1 d . . . . .
C13 C 1.1293(2) 0.34016(10) 0.01660(9) 0.0310(2) Uani 1 1 d . . . . .
H13 H 1.2216 0.3950 0.0133 0.037 Uiso 1 1 calc R . . . .
C14 C 1.0115(2) 0.33114(11) -0.06517(9) 0.0346(3) Uani 1 1 d . . . . .
H14 H 1.0238 0.3797 -0.1242 0.041 Uiso 1 1 calc R . . . .
C15 C 0.8768(2) 0.25135(11) -0.06029(9) 0.0354(3) Uani 1 1 d . . . . .
H15 H 0.7979 0.2444 -0.1163 0.042 Uiso 1 1 calc R . . . .
C16 C 0.8572(2) 0.18117(10) 0.02710(9) 0.0309(2) Uani 1 1 d . . . . .
H16 H 0.7628 0.1272 0.0307 0.037 Uiso 1 1 calc R . . . .
C21 C 1.5428(2) -0.08315(10) 0.16934(11) 0.0367(3) Uani 1 1 d . . . . .
H21 H 1.6649 -0.1122 0.1134 0.044 Uiso 1 1 calc R . . . .
C22 C 1.3470(2) -0.00451(10) 0.14922(9) 0.0303(2) Uani 1 1 d . . . . .
H22 H 1.3378 0.0204 0.0795 0.036 Uiso 1 1 calc R . . . .
C18 C 1.1828(2) 0.00110(11) 0.33174(9) 0.0341(3) Uani 1 1 d . . . . .
H18 H 1.0600 0.0287 0.3877 0.041 Uiso 1 1 calc R . . . .
C19 C 1.3802(3) -0.07622(12) 0.35199(11) 0.0423(3) Uani 1 1 d . . . . .
H19 H 1.3918 -0.0998 0.4219 0.051 Uiso 1 1 calc R . . . .
C24 C -0.5336(2) 0.52001(12) 0.83215(10) 0.0371(3) Uani 1 1 d . . . . .
H24A H -0.6282 0.5181 0.7784 0.056 Uiso 1 1 calc GR . . . .
H24B H -0.6163 0.5785 0.8867 0.056 Uiso 1 1 calc GR . . . .
H24C H -0.4987 0.4432 0.8637 0.056 Uiso 1 1 calc GR . . . .
C20 C 1.5592(2) -0.11889(11) 0.27118(12) 0.0417(3) Uani 1 1 d . . . . .
H20 H 1.6925 -0.1723 0.2853 0.050 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
O C8 1.3654(13) . ?
O C24 1.4242(14) . ?
N C1 1.4717(13) . ?
N C2 1.2777(14) . ?
C5 C4 1.4596(15) . ?
C5 C6 1.4041(15) . ?
C5 C10 1.3942(15) . ?
C4 C3 1.3415(15) . ?
C3 C2 1.4497(15) . ?
C1 C11 1.5177(14) . ?
C1 C17 1.5260(15) . ?
C6 C7 1.3783(15) . ?
C7 C8 1.3999(15) . ?
C12 C11 1.3937(15) . ?
C12 C13 1.3915(15) . ?
C8 C9 1.3900(16) . ?
C10 C9 1.3943(15) . ?
C11 C16 1.3950(14) . ?
C17 C22 1.3926(16) . ?
C17 C18 1.3978(15) . ?
C13 C14 1.3944(17) . ?
C14 C15 1.3831(19) . ?
C15 C16 1.3951(16) . ?
C21 C22 1.3941(17) . ?
C21 C20 1.3881(19) . ?
C18 C19 1.3945(19) . ?
C19 C20 1.384(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
C8 O C24 117.97(9) . . ?
C2 N C1 116.12(9) . . ?
C6 C5 C4 123.26(10) . . ?
C10 C5 C4 119.20(10) . . ?
C10 C5 C6 117.49(10) . . ?
C3 C4 C5 127.65(10) . . ?
C4 C3 C2 121.22(10) . . ?
N C1 C11 107.82(8) . . ?
N C1 C17 110.40(8) . . ?
C11 C1 C17 113.89(8) . . ?
C7 C6 C5 121.25(10) . . ?
C6 C7 C8 120.20(10) . . ?
N C2 C3 122.47(10) . . ?
C13 C12 C11 120.29(10) . . ?
O C8 C7 115.33(10) . . ?
O C8 C9 124.80(10) . . ?
C9 C8 C7 119.87(10) . . ?
C5 C10 C9 122.17(10) . . ?
C8 C9 C10 119.01(10) . . ?
C12 C11 C1 120.33(9) . . ?
C12 C11 C16 119.02(10) . . ?
C16 C11 C1 120.57(10) . . ?
C22 C17 C1 121.21(9) . . ?
C22 C17 C18 118.40(10) . . ?
C18 C17 C1 120.28(10) . . ?
C12 C13 C14 120.20(11) . . ?
C15 C14 C13 119.93(11) . . ?
C14 C15 C16 119.80(11) . . ?
C11 C16 C15 120.75(11) . . ?
C20 C21 C22 119.92(12) . . ?
C17 C22 C21 121.12(11) . . ?
C19 C18 C17 120.41(12) . . ?
C20 C19 C18 120.58(12) . . ?
C19 C20 C21 119.56(12) . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 1 0.0476 0.0003 -0.0001 1.0003 0.0214 0.0515 0.0008
0 0 -1 0.0476 -0.0003 0.0001 -1.0003 -0.0214 -0.0515 -0.0008
0 -1 0 0.1354 0.0003 -0.9994 0.0000 -0.0566 0.0217 0.0118
0 1 0 0.1354 -0.0003 0.9994 -0.0000 0.0566 -0.0217 -0.0118
1 2 1 0.2289 1.0000 2.0003 1.0010 0.1213 -0.0105 0.0961
-3 -1 -1 0.3316 -3.0006 -1.0043 -1.0025 -0.0381 0.0262 -0.3455

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2e
_audit_block_doi                 10.5517/cc13xm3r
_database_code_depnum_ccdc_archive 'CCDC 1040394'
_audit_update_record             
;
2014-12-19 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;

_audit_creation_date             2014-10-31
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.10.30 svn.r3070 for OlexSys, GUI svn.r4932)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 Cl N'
_chemical_formula_sum            'C22 H18 Cl N'
_chemical_formula_weight         331.82
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6806(5)
_cell_length_b                   12.4099(9)
_cell_length_c                   12.5191(9)
_cell_angle_alpha                89.497(4)
_cell_angle_beta                 79.611(4)
_cell_angle_gamma                78.354(4)
_cell_volume                     849.85(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3112
_cell_measurement_temperature    120
_cell_measurement_theta_max      73.52
_cell_measurement_theta_min      3.59
_shelx_estimated_absorpt_T_max   0.922
_shelx_estimated_absorpt_T_min   0.336
_exptl_absorpt_coefficient_mu    1.977
_exptl_absorpt_correction_T_max  0.9534
_exptl_absorpt_correction_T_min  0.5673
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
SADABS-2009/1 (Bruker,2010) was used for absorption correction.
wR2(int) was 0.1563 before and 0.0830 after correction.
The Ratio of minimum to maximum transmission is 0.5278.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             348
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 2.00 0.0040
0.00 1.00 -2.00 0.0210
-1.00 0.00 0.00 0.3040
1.00 0.00 0.00 0.3320
0.00 1.00 1.00 0.0250
0.00 -1.00 -1.00 0.0240

_exptl_crystal_size_max          0.705
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.042
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_unetI/netI     0.0820
_diffrn_reflns_Laue_measured_fraction_full 0.902
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5801
_diffrn_reflns_point_group_measured_fraction_full 0.902
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         73.674
_diffrn_reflns_theta_min         3.591
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.902
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'ImuS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2399
_reflns_number_total             3006
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3006
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0788
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1550P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2033
_refine_ls_wR_factor_ref         0.2178
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C10(H10), C3(H3), C12(H12), C16(H16), C7(H7), C4(H4), C19(H19),
 C9(H9), C6(H6), C13(H13), C20(H20), C22(H22), C14(H14), C18(H18), C15(H15),
 C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl 1.18949(14) 0.82769(6) -0.05879(6) 0.0382(3) Uani 1 1 d . . . . .
N N 0.3444(5) 0.31690(19) 0.3001(2) 0.0296(6) Uani 1 1 d . . . . .
C2 C 0.5366(6) 0.3571(2) 0.2881(2) 0.0300(6) Uani 1 1 d . . . . .
H2 H 0.6567 0.3288 0.3306 0.036 Uiso 1 1 calc R . . . .
C10 C 1.0291(6) 0.6295(3) 0.1832(3) 0.0316(7) Uani 1 1 d . . . . .
H10 H 1.0797 0.6105 0.2504 0.038 Uiso 1 1 calc R . . . .
C3 C 0.5829(5) 0.4438(2) 0.2134(2) 0.0297(6) Uani 1 1 d . . . . .
H3 H 0.4777 0.4673 0.1630 0.036 Uiso 1 1 calc R . . . .
C12 C 0.2503(6) 0.1000(2) 0.2374(3) 0.0323(7) Uani 1 1 d . . . . .
H12 H 0.1006 0.1503 0.2363 0.039 Uiso 1 1 calc R . . . .
C16 C 0.6165(6) 0.0433(2) 0.3112(3) 0.0352(7) Uani 1 1 d . . . . .
H16 H 0.7186 0.0553 0.3604 0.042 Uiso 1 1 calc R . . . .
C8 C 1.0532(6) 0.7346(2) 0.0224(3) 0.0306(6) Uani 1 1 d . . . . .
C17 C 0.0972(5) 0.2434(2) 0.4553(2) 0.0295(6) Uani 1 1 d . . . . .
C7 C 0.8781(5) 0.6867(2) -0.0128(3) 0.0303(6) Uani 1 1 d . . . . .
H7 H 0.8262 0.7070 -0.0795 0.036 Uiso 1 1 calc R . . . .
C4 C 0.7748(6) 0.4904(2) 0.2160(3) 0.0327(7) Uani 1 1 d . . . . .
H4 H 0.8716 0.4627 0.2685 0.039 Uiso 1 1 calc R . . . .
C1 C 0.3399(5) 0.2251(2) 0.3766(2) 0.0286(6) Uani 1 1 d . . . . .
H1 H 0.4726 0.2240 0.4196 0.034 Uiso 1 1 calc R . . . .
C19 C -0.2578(6) 0.3650(3) 0.5570(3) 0.0367(7) Uani 1 1 d . . . . .
H19 H -0.3503 0.4375 0.5739 0.044 Uiso 1 1 calc R . . . .
C9 C 1.1282(6) 0.7079(2) 0.1206(3) 0.0318(7) Uani 1 1 d . . . . .
H9 H 1.2449 0.7426 0.1444 0.038 Uiso 1 1 calc R . . . .
C11 C 0.4006(5) 0.1187(2) 0.3081(2) 0.0296(6) Uani 1 1 d . . . . .
C5 C 0.8564(5) 0.5778(2) 0.1496(2) 0.0286(6) Uani 1 1 d . . . . .
C6 C 0.7810(5) 0.6089(2) 0.0510(2) 0.0307(7) Uani 1 1 d . . . . .
H6 H 0.6611 0.5760 0.0276 0.037 Uiso 1 1 calc R . . . .
C13 C 0.3188(6) 0.0072(3) 0.1678(3) 0.0373(7) Uani 1 1 d . . . . .
H13 H 0.2172 -0.0049 0.1185 0.045 Uiso 1 1 calc R . . . .
C20 C -0.3393(6) 0.2763(3) 0.6080(3) 0.0378(7) Uani 1 1 d . . . . .
H20 H -0.4884 0.2877 0.6590 0.045 Uiso 1 1 calc R . . . .
C22 C 0.0158(6) 0.1540(3) 0.5080(3) 0.0346(7) Uani 1 1 d . . . . .
H22 H 0.1092 0.0816 0.4917 0.042 Uiso 1 1 calc R . . . .
C14 C 0.5366(6) -0.0677(3) 0.1708(3) 0.0399(8) Uani 1 1 d . . . . .
H14 H 0.5836 -0.1309 0.1235 0.048 Uiso 1 1 calc R . . . .
C18 C -0.0416(6) 0.3485(2) 0.4814(2) 0.0333(7) Uani 1 1 d . . . . .
H18 H 0.0121 0.4100 0.4470 0.040 Uiso 1 1 calc R . . . .
C15 C 0.6835(6) -0.0497(3) 0.2427(3) 0.0423(8) Uani 1 1 d . . . . .
H15 H 0.8309 -0.1010 0.2453 0.051 Uiso 1 1 calc R . . . .
C21 C -0.2017(6) 0.1705(3) 0.5841(3) 0.0381(7) Uani 1 1 d . . . . .
H21 H -0.2553 0.1095 0.6196 0.046 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
Cl C8 1.738(3) . ?
N C2 1.274(4) . ?
N C1 1.483(4) . ?
C2 C3 1.453(4) . ?
C10 C9 1.388(4) . ?
C10 C5 1.400(4) . ?
C3 C4 1.339(4) . ?
C12 C11 1.387(4) . ?
C12 C13 1.396(4) . ?
C16 C11 1.391(4) . ?
C16 C15 1.391(5) . ?
C8 C7 1.393(4) . ?
C8 C9 1.389(4) . ?
C17 C1 1.520(4) . ?
C17 C22 1.401(4) . ?
C17 C18 1.388(4) . ?
C7 C6 1.384(4) . ?
C4 C5 1.460(4) . ?
C1 C11 1.526(4) . ?
C19 C20 1.386(5) . ?
C19 C18 1.389(5) . ?
C5 C6 1.404(4) . ?
C13 C14 1.396(5) . ?
C20 C21 1.390(5) . ?
C22 C21 1.398(5) . ?
C14 C15 1.380(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
C2 N C1 115.0(2) . . ?
N C2 C3 123.9(3) . . ?
C9 C10 C5 121.5(3) . . ?
C4 C3 C2 119.5(3) . . ?
C11 C12 C13 120.0(3) . . ?
C15 C16 C11 120.3(3) . . ?
C7 C8 Cl 120.1(2) . . ?
C9 C8 Cl 118.4(2) . . ?
C9 C8 C7 121.6(3) . . ?
C22 C17 C1 120.1(3) . . ?
C18 C17 C1 121.3(3) . . ?
C18 C17 C22 118.5(3) . . ?
C6 C7 C8 118.9(3) . . ?
C3 C4 C5 129.1(3) . . ?
N C1 C17 110.4(2) . . ?
N C1 C11 107.0(2) . . ?
C17 C1 C11 114.9(2) . . ?
C20 C19 C18 120.3(3) . . ?
C10 C9 C8 118.7(3) . . ?
C12 C11 C16 119.7(3) . . ?
C12 C11 C1 120.5(3) . . ?
C16 C11 C1 119.7(3) . . ?
C10 C5 C4 118.1(3) . . ?
C10 C5 C6 118.2(3) . . ?
C6 C5 C4 123.7(3) . . ?
C7 C6 C5 121.2(3) . . ?
C14 C13 C12 120.0(3) . . ?
C19 C20 C21 119.6(3) . . ?
C21 C22 C17 120.6(3) . . ?
C15 C14 C13 119.8(3) . . ?
C17 C18 C19 121.0(3) . . ?
C14 C15 C16 120.3(3) . . ?
C20 C21 C22 120.0(3) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2h
_audit_block_doi                 10.5517/cc13xm4s
_database_code_depnum_ccdc_archive 'CCDC 1040395'
_audit_update_record             
;
2014-12-19 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;

_audit_creation_date             2014-11-04
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.11.03 svn.r3071 for OlexSys, GUI svn.r4932)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 N'
_chemical_formula_sum            'C23 H21 N'
_chemical_formula_weight         311.41
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1195(5)
_cell_length_b                   8.1503(7)
_cell_length_c                   34.905(3)
_cell_angle_alpha                93.937(3)
_cell_angle_beta                 93.167(3)
_cell_angle_gamma                95.383(3)
_cell_volume                     1725.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6492
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.517
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2009/1 (Bruker,2010) was used for absorption correction.
wR2(int) was 0.1402 before and 0.1050 after correction.
The Ratio of minimum to maximum transmission is 0.5359.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -2.00 -1.00 0.0570
0.00 2.00 1.00 0.0410
0.00 0.00 -1.00 0.0720
0.00 0.00 1.00 0.0750
-1.00 0.00 1.00 0.0940
1.00 0.00 -1.00 0.1030
1.00 -2.00 2.00 0.0960

_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.114
_exptl_special_details           
;
The data collection nominally covered full sphere of reciprocal 
space, by a combination of 3 runs of narrow-frame ω-scans (scan 
width 0.5° ω, 10s exposure), every run at a different φ angle. 
Crystal to detector distance 4.00 cm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_av_unetI/netI     0.0729
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            18314
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.626
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'ImuS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4453
_reflns_number_total             6066
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  
'SHELXL 2014/7 multi-CPU version (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         6066
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0644
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1100P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1598
_refine_ls_wR_factor_ref         0.1784
_refine_special_details          
;
 Methyl groups were refined as rigid bodies rotating around C---C 
 bonds, with a common refined U for three H atoms. Other H atoms: 
 riding model (constr).
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Uiso(H23A)=Uiso(H24A)=Uiso(H25A)=FVAR(1)
 Uiso(H23B)=Uiso(H24B)=Uiso(H25B)=FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C1A(H1A), C1B(H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C4A(H4A), C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A), C10A(H10A),
 C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A), C16A(H16A), C18A(H18A),
 C19A(H19A), C20A(H20A), C21A(H21A), C22A(H22A), C2B(H2B), C4B(H4B), C6B(H6B),
 C7B(H7B), C8B(H8B), C9B(H9B), C10B(H10B), C12B(H12B), C13B(H13B), C14B(H14B),
 C15B(H15B), C16B(H16B), C18B(H18B), C19B(H19B), C20B(H20B), C21B(H21B),
 C22B(H22B)
3.c Idealised Me refined as rotating group:
 C23A(H23A,H24A,H25A), C23B(H23B,H24B,H25B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 0.5752(2) 0.16081(17) 0.12569(4) 0.0226(4) Uani 1 1 d . . . . .
C1A C 0.7308(3) 0.0653(2) 0.10547(5) 0.0220(4) Uani 1 1 d . . . . .
H1A H 0.8706 0.0710 0.1220 0.026 Uiso 1 1 calc R . . . .
C2A C 0.6357(3) 0.2184(2) 0.15978(5) 0.0226(4) Uani 1 1 d . . . . .
H2A H 0.7742 0.1938 0.1704 0.027 Uiso 1 1 calc R . . . .
C3A C 0.5036(3) 0.3208(2) 0.18373(5) 0.0221(4) Uani 1 1 d . . . . .
C4A C 0.5955(3) 0.3771(2) 0.21865(5) 0.0253(4) Uani 1 1 d . . . . .
H4A H 0.7335 0.3376 0.2247 0.030 Uiso 1 1 calc R . . . .
C5A C 0.5212(3) 0.4883(2) 0.24895(5) 0.0249(4) Uani 1 1 d . . . . .
C6A C 0.3172(3) 0.5525(2) 0.24907(6) 0.0319(5) Uani 1 1 d . . . . .
H6A H 0.2090 0.5188 0.2288 0.038 Uiso 1 1 calc R . . . .
C7A C 0.2712(3) 0.6644(2) 0.27835(6) 0.0349(5) Uani 1 1 d . . . . .
H7A H 0.1323 0.7077 0.2778 0.042 Uiso 1 1 calc R . . . .
C8A C 0.4235(4) 0.7141(2) 0.30830(6) 0.0359(5) Uani 1 1 d . . . . .
H8A H 0.3901 0.7908 0.3284 0.043 Uiso 1 1 calc R . . . .
C9A C 0.6257(4) 0.6512(2) 0.30896(5) 0.0348(5) Uani 1 1 d . . . . .
H9A H 0.7326 0.6855 0.3294 0.042 Uiso 1 1 calc R . . . .
C10A C 0.6720(3) 0.5392(2) 0.28002(5) 0.0289(5) Uani 1 1 d . . . . .
H10A H 0.8103 0.4950 0.2812 0.035 Uiso 1 1 calc R . . . .
C11A C 0.7804(3) 0.1425(2) 0.06799(5) 0.0215(4) Uani 1 1 d . . . . .
C12A C 0.6107(3) 0.1536(2) 0.04019(5) 0.0240(4) Uani 1 1 d . . . . .
H12A H 0.4648 0.1118 0.0446 0.029 Uiso 1 1 calc R . . . .
C13A C 0.6537(3) 0.2252(2) 0.00615(5) 0.0268(5) Uani 1 1 d . . . . .
H13A H 0.5374 0.2332 -0.0126 0.032 Uiso 1 1 calc R . . . .
C14A C 0.8660(3) 0.2847(2) -0.00044(5) 0.0278(5) Uani 1 1 d . . . . .
H14A H 0.8951 0.3351 -0.0236 0.033 Uiso 1 1 calc R . . . .
C15A C 1.0367(3) 0.2716(2) 0.02650(5) 0.0292(5) Uani 1 1 d . . . . .
H15A H 1.1830 0.3108 0.0217 0.035 Uiso 1 1 calc R . . . .
C16A C 0.9931(3) 0.2005(2) 0.06072(5) 0.0250(4) Uani 1 1 d . . . . .
H16A H 1.1101 0.1916 0.0793 0.030 Uiso 1 1 calc R . . . .
C17A C 0.6405(3) -0.1146(2) 0.09797(5) 0.0218(4) Uani 1 1 d . . . . .
C18A C 0.4267(3) -0.1721(2) 0.10486(5) 0.0241(4) Uani 1 1 d . . . . .
H18A H 0.3284 -0.0970 0.1141 0.029 Uiso 1 1 calc R . . . .
C19A C 0.3559(3) -0.3393(2) 0.09832(5) 0.0257(4) Uani 1 1 d . . . . .
H19A H 0.2092 -0.3776 0.1031 0.031 Uiso 1 1 calc R . . . .
C20A C 0.4960(3) -0.4501(2) 0.08504(5) 0.0272(5) Uani 1 1 d . . . . .
H20A H 0.4473 -0.5645 0.0811 0.033 Uiso 1 1 calc R . . . .
C21A C 0.7087(3) -0.3934(2) 0.07743(5) 0.0287(5) Uani 1 1 d . . . . .
H21A H 0.8056 -0.4687 0.0679 0.034 Uiso 1 1 calc R . . . .
C22A C 0.7798(3) -0.2271(2) 0.08377(5) 0.0250(4) Uani 1 1 d . . . . .
H22A H 0.9256 -0.1890 0.0784 0.030 Uiso 1 1 calc R . . . .
C23A C 0.2833(3) 0.3562(2) 0.16716(5) 0.0304(5) Uani 1 1 d . . . . .
H23A H 0.1678 0.3076 0.1825 0.042(3) Uiso 1 1 calc GR . . . .
H24A H 0.2613 0.3081 0.1406 0.042(3) Uiso 1 1 calc GR . . . .
H25A H 0.2767 0.4760 0.1676 0.042(3) Uiso 1 1 calc GR . . . .
N1B N 0.9100(2) 0.34186(18) 0.37278(4) 0.0220(4) Uani 1 1 d . . . . .
C1B C 0.7615(3) 0.4355(2) 0.39541(5) 0.0226(4) Uani 1 1 d . . . . .
H1B H 0.6178 0.4315 0.3801 0.027 Uiso 1 1 calc R . . . .
C2B C 0.8237(3) 0.2611(2) 0.34244(5) 0.0227(4) Uani 1 1 d . . . . .
H2B H 0.6693 0.2588 0.3374 0.027 Uiso 1 1 calc R . . . .
C3B C 0.9486(3) 0.1711(2) 0.31462(5) 0.0231(4) Uani 1 1 d . . . . .
C4B C 0.8327(3) 0.0964(2) 0.28342(5) 0.0240(4) Uani 1 1 d . . . . .
H4B H 0.6784 0.1023 0.2835 0.029 Uiso 1 1 calc R . . . .
C5B C 0.9050(3) 0.0074(2) 0.24918(5) 0.0227(4) Uani 1 1 d . . . . .
C6B C 1.1109(3) 0.0400(2) 0.23439(5) 0.0262(5) Uani 1 1 d . . . . .
H6B H 1.2141 0.1233 0.2470 0.031 Uiso 1 1 calc R . . . .
C7B C 1.1662(3) -0.0473(2) 0.20163(5) 0.0279(5) Uani 1 1 d . . . . .
H7B H 1.3073 -0.0244 0.1920 0.033 Uiso 1 1 calc R . . . .
C8B C 1.0171(3) -0.1680(2) 0.18269(5) 0.0292(5) Uani 1 1 d . . . . .
H8B H 1.0563 -0.2287 0.1603 0.035 Uiso 1 1 calc R . . . .
C9B C 0.8107(3) -0.2001(2) 0.19636(5) 0.0283(5) Uani 1 1 d . . . . .
H9B H 0.7072 -0.2820 0.1833 0.034 Uiso 1 1 calc R . . . .
C10B C 0.7556(3) -0.1125(2) 0.22922(5) 0.0263(4) Uani 1 1 d . . . . .
H10B H 0.6132 -0.1345 0.2384 0.032 Uiso 1 1 calc R . . . .
C11B C 0.7196(3) 0.3565(2) 0.43283(5) 0.0223(4) Uani 1 1 d . . . . .
C12B C 0.8912(3) 0.3469(2) 0.46019(5) 0.0252(4) Uani 1 1 d . . . . .
H12B H 1.0360 0.3907 0.4556 0.030 Uiso 1 1 calc R . . . .
C13B C 0.8515(3) 0.2739(2) 0.49407(5) 0.0277(5) Uani 1 1 d . . . . .
H13B H 0.9694 0.2662 0.5125 0.033 Uiso 1 1 calc R . . . .
C14B C 0.6404(3) 0.2120(2) 0.50105(5) 0.0281(5) Uani 1 1 d . . . . .
H14B H 0.6137 0.1617 0.5243 0.034 Uiso 1 1 calc R . . . .
C15B C 0.4687(3) 0.2230(2) 0.47445(5) 0.0305(5) Uani 1 1 d . . . . .
H15B H 0.3236 0.1814 0.4794 0.037 Uiso 1 1 calc R . . . .
C16B C 0.5083(3) 0.2951(2) 0.44033(5) 0.0263(5) Uani 1 1 d . . . . .
H16B H 0.3899 0.3025 0.4220 0.032 Uiso 1 1 calc R . . . .
C17B C 0.8539(3) 0.6153(2) 0.40226(5) 0.0214(4) Uani 1 1 d . . . . .
C18B C 1.0644(3) 0.6720(2) 0.39387(5) 0.0261(5) Uani 1 1 d . . . . .
H18B H 1.1604 0.5961 0.3842 0.031 Uiso 1 1 calc R . . . .
C19B C 1.1375(3) 0.8397(2) 0.39938(5) 0.0273(5) Uani 1 1 d . . . . .
H19B H 1.2828 0.8772 0.3936 0.033 Uiso 1 1 calc R . . . .
C20B C 0.9992(3) 0.9511(2) 0.41320(5) 0.0281(5) Uani 1 1 d . . . . .
H20B H 1.0479 1.0656 0.4165 0.034 Uiso 1 1 calc R . . . .
C21B C 0.7896(3) 0.8953(2) 0.42229(6) 0.0309(5) Uani 1 1 d . . . . .
H21B H 0.6947 0.9714 0.4323 0.037 Uiso 1 1 calc R . . . .
C22B C 0.7177(3) 0.7288(2) 0.41689(5) 0.0261(5) Uani 1 1 d . . . . .
H22B H 0.5734 0.6914 0.4233 0.031 Uiso 1 1 calc R . . . .
C23B C 1.1923(3) 0.1768(2) 0.32297(5) 0.0282(5) Uani 1 1 d . . . . .
H23B H 1.2470 0.0796 0.3101 0.035(3) Uiso 1 1 calc GR . . . .
H24B H 1.2245 0.1773 0.3508 0.035(3) Uiso 1 1 calc GR . . . .
H25B H 1.2645 0.2773 0.3135 0.035(3) Uiso 1 1 calc GR . . . .


_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
N1A C1A 1.466(2) . ?
N1A C2A 1.271(2) . ?
C1A C11A 1.523(2) . ?
C1A C17A 1.518(2) . ?
C2A C3A 1.468(2) . ?
C3A C4A 1.346(2) . ?
C3A C23A 1.498(2) . ?
C4A C5A 1.464(2) . ?
C5A C6A 1.398(3) . ?
C5A C10A 1.399(3) . ?
C6A C7A 1.381(2) . ?
C7A C8A 1.374(3) . ?
C8A C9A 1.383(3) . ?
C9A C10A 1.374(2) . ?
C11A C12A 1.395(2) . ?
C11A C16A 1.385(3) . ?
C12A C13A 1.386(2) . ?
C13A C14A 1.381(3) . ?
C14A C15A 1.383(3) . ?
C15A C16A 1.391(3) . ?
C17A C18A 1.387(3) . ?
C17A C22A 1.394(2) . ?
C18A C19A 1.390(3) . ?
C19A C20A 1.378(3) . ?
C20A C21A 1.386(3) . ?
C21A C22A 1.383(3) . ?
N1B C1B 1.470(2) . ?
N1B C2B 1.269(2) . ?
C1B C11B 1.519(2) . ?
C1B C17B 1.518(3) . ?
C2B C3B 1.468(2) . ?
C3B C4B 1.343(2) . ?
C3B C23B 1.499(2) . ?
C4B C5B 1.466(2) . ?
C5B C6B 1.397(3) . ?
C5B C10B 1.394(2) . ?
C6B C7B 1.380(2) . ?
C7B C8B 1.383(3) . ?
C8B C9B 1.383(3) . ?
C9B C10B 1.384(2) . ?
C11B C12B 1.391(2) . ?
C11B C16B 1.388(3) . ?
C12B C13B 1.383(3) . ?
C13B C14B 1.383(3) . ?
C14B C15B 1.377(3) . ?
C15B C16B 1.387(3) . ?
C17B C18B 1.381(3) . ?
C17B C22B 1.392(2) . ?
C18B C19B 1.394(3) . ?
C19B C20B 1.380(3) . ?
C20B C21B 1.381(3) . ?
C21B C22B 1.384(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
C2A N1A C1A 116.46(15) . . ?
N1A C1A C11A 109.08(14) . . ?
N1A C1A C17A 111.04(15) . . ?
C17A C1A C11A 111.02(14) . . ?
N1A C2A C3A 123.71(17) . . ?
C2A C3A C23A 117.85(15) . . ?
C4A C3A C2A 116.15(16) . . ?
C4A C3A C23A 125.99(16) . . ?
C3A C4A C5A 131.64(18) . . ?
C6A C5A C4A 126.20(17) . . ?
C6A C5A C10A 117.13(17) . . ?
C10A C5A C4A 116.64(17) . . ?
C7A C6A C5A 120.74(18) . . ?
C8A C7A C6A 120.95(19) . . ?
C7A C8A C9A 119.34(18) . . ?
C10A C9A C8A 119.99(19) . . ?
C9A C10A C5A 121.82(19) . . ?
C12A C11A C1A 119.96(16) . . ?
C16A C11A C1A 120.96(16) . . ?
C16A C11A C12A 119.07(17) . . ?
C13A C12A C11A 120.43(17) . . ?
C14A C13A C12A 119.85(18) . . ?
C13A C14A C15A 120.40(18) . . ?
C14A C15A C16A 119.65(18) . . ?
C11A C16A C15A 120.57(17) . . ?
C18A C17A C1A 122.99(16) . . ?
C18A C17A C22A 118.68(17) . . ?
C22A C17A C1A 118.33(16) . . ?
C17A C18A C19A 120.12(17) . . ?
C20A C19A C18A 120.81(18) . . ?
C19A C20A C21A 119.44(17) . . ?
C22A C21A C20A 120.00(17) . . ?
C21A C22A C17A 120.92(18) . . ?
C2B N1B C1B 115.97(15) . . ?
N1B C1B C11B 110.43(14) . . ?
N1B C1B C17B 110.29(15) . . ?
C17B C1B C11B 112.03(14) . . ?
N1B C2B C3B 123.86(17) . . ?
C2B C3B C23B 117.24(15) . . ?
C4B C3B C2B 116.16(16) . . ?
C4B C3B C23B 126.56(16) . . ?
C3B C4B C5B 130.61(17) . . ?
C6B C5B C4B 124.09(16) . . ?
C10B C5B C4B 117.91(17) . . ?
C10B C5B C6B 117.94(17) . . ?
C7B C6B C5B 120.84(17) . . ?
C6B C7B C8B 120.27(18) . . ?
C7B C8B C9B 119.94(18) . . ?
C8B C9B C10B 119.69(18) . . ?
C9B C10B C5B 121.30(18) . . ?
C12B C11B C1B 120.64(17) . . ?
C16B C11B C1B 120.15(16) . . ?
C16B C11B C12B 119.20(17) . . ?
C13B C12B C11B 120.19(18) . . ?
C12B C13B C14B 120.01(18) . . ?
C15B C14B C13B 120.32(18) . . ?
C14B C15B C16B 119.77(18) . . ?
C15B C16B C11B 120.49(18) . . ?
C18B C17B C1B 123.21(16) . . ?
C18B C17B C22B 118.53(17) . . ?
C22B C17B C1B 118.24(16) . . ?
C17B C18B C19B 120.67(18) . . ?
C20B C19B C18B 120.13(18) . . ?
C19B C20B C21B 119.68(18) . . ?
C20B C21B C22B 120.05(18) . . ?
C21B C22B C17B 120.91(18) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'

#===END
####################################################################### 
# 
# 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_2j
_database_code_depnum_ccdc_archive 'CCDC 1040594'
_audit_update_record             
;
2014-12-21 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;

_audit_creation_date             2014-10-30
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.10.28 svn.r3060 for OlexSys, GUI svn.r4931)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 N S'
_chemical_formula_sum            'C20 H17 N S'
_chemical_formula_weight         303.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H17 N S'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.04042(15)
_cell_length_b                   11.6602(3)
_cell_length_c                   12.1628(2)
_cell_angle_alpha                99.3522(19)
_cell_angle_beta                 98.9080(19)
_cell_angle_gamma                101.371(2)
_cell_volume                     813.07(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5194
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.8030
_cell_measurement_theta_min      1.8030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.927
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 
(release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 
2014,18:38:05) 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_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.5195
_exptl_crystal_size_mid          0.3634
_exptl_crystal_size_min          0.1745
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12662
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.352
_diffrn_reflns_theta_min         2.246
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.15
_diffrn_detector_type            'Sapphire3 CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -24.00   21.00   0.3000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5469 -100.0000  -90.0000 150

#__ type_ start__ end____ width___ exp.time_
  2 omega  -24.00   60.00   0.3000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.3282 -100.0000 -120.0000 280

#__ type_ start__ end____ width___ exp.time_
  3 omega    2.00   89.00   0.3000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.3282   57.0000  120.0000 290

#__ type_ start__ end____ width___ exp.time_
  4 omega    2.00   89.00   0.3000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.3282   57.0000   30.0000 290

#__ type_ start__ end____ width___ exp.time_
  5 omega  -51.00   91.20   0.3000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.3282    0.0000 -150.0000 474

#__ type_ start__ end____ width___ exp.time_
  6 omega   32.00   95.00   0.3000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.3282 -178.0000 -150.0000 210

#__ type_ start__ end____ width___ exp.time_
  7 omega  -24.00   21.00   0.3000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5469 -100.0000  120.0000 150

#__ type_ start__ end____ width___ exp.time_
  8 omega   -2.00   91.00   0.3000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.3282   38.0000    0.0000 310

#__ type_ start__ end____ width___ exp.time_
  9 omega    5.00   46.40   0.3000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.3282 -137.0000   72.5717 138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies, Gemini S Ultra kappa-diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0110576000
_diffrn_orient_matrix_UB_12      -0.0567012000
_diffrn_orient_matrix_UB_13      0.0110418000
_diffrn_orient_matrix_UB_21      -0.1192601000
_diffrn_orient_matrix_UB_22      -0.0232051000
_diffrn_orient_matrix_UB_23      -0.0217895000
_diffrn_orient_matrix_UB_31      0.0236098000
_diffrn_orient_matrix_UB_32      -0.0159932000
_diffrn_orient_matrix_UB_33      -0.0550626000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3829
_reflns_number_total             4269
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 
(release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 
(release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 
(release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  
'SHELXL 2014/7 multi-CPU version (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+0.3740P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1085
_refine_special_details          
; S and C(6) atoms are statistically mixed, i.e. thiophene ring is 
disordered between two orientations differing by a 180 deg rotation 
around the V(4)---C(5) bond, in a 0.8:0.2 ratio (minor component 
primed).
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{S, C6'}
{S', C6}
3. Uiso/Uaniso restraints and constraints
Uanis(S) = Uanis(C6')
Uanis(S') = Uanis(C6)
4. Others
 Fixed Sof: S(0.8) C6'(0.2) H6'(0.2) C6(0.8) H6(0.8) S'(0.2)
5.a Riding coordinates:
 C6(H6), C7(H7), C8(H8)
5.b Ternary CH refined with riding coordinates:
 C1(H1)
5.c Aromatic/amide H refined with riding coordinates:
 C6'(H6'), C2(H2), C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.22582(6) -0.00327(3) 0.62163(3) 0.02322(11) Uani 0.8 1 d . . P A 1
C6' C 0.22582(6) -0.00327(3) 0.62163(3) 0.02322(11) Uani 0.2 1 d . . P A 2
H6' H 0.0787 -0.0098 0.5768 0.028 Uiso 0.2 1 calc R . P A 2
N N 0.24852(18) 0.30775(9) 0.34639(8) 0.0189(2) Uani 1 1 d . . . . .
C1 C 0.3151(2) 0.38856(10) 0.26943(9) 0.0169(2) Uani 1 1 d . . . . .
H1 H 0.4770 0.4350 0.2998 0.020 Uiso 1 1 calc R . . . .
C2 C 0.4096(2) 0.29399(11) 0.42164(10) 0.0191(2) Uani 1 1 d . . . . .
H2 H 0.5615 0.3404 0.4303 0.023 Uiso 1 1 calc R . . . .
C3 C 0.3613(2) 0.20782(11) 0.49382(10) 0.0198(2) Uani 1 1 d . . . . .
H3 H 0.2068 0.1649 0.4857 0.024 Uiso 1 1 calc R . . . .
C4 C 0.5235(2) 0.18537(11) 0.57157(10) 0.0206(2) Uani 1 1 d . . . . .
H4 H 0.6747 0.2340 0.5845 0.025 Uiso 1 1 calc R . . . .
C5 C 0.4837(2) 0.09216(11) 0.63708(10) 0.0206(2) Uani 1 1 d . . . . .
C6 C 0.66023(15) 0.06012(8) 0.72088(7) 0.02879(19) Uani 0.8 1 d . . P A 1
H6 H 0.8144 0.0995 0.7435 0.035 Uiso 0.8 1 d R . P A 1
S' S 0.66023(15) 0.06012(8) 0.72088(7) 0.02879(19) Uani 0.2 1 d . . P A 2
C7 C 0.5501(3) -0.04065(13) 0.75917(11) 0.0345(3) Uani 1 1 d . . . . .
H7 H 0.6283 -0.0760 0.8114 0.041 Uiso 1 1 d R . . A .
C8 C 0.3241(3) -0.08221(13) 0.71416(12) 0.0354(3) Uani 1 1 d . . . . .
H8 H 0.2322 -0.1477 0.7323 0.042 Uiso 1 1 d R . . A .
C11 C 0.3050(2) 0.31135(10) 0.15423(10) 0.0175(2) Uani 1 1 d . . . . .
C12 C 0.1013(2) 0.22939(11) 0.09866(10) 0.0224(2) Uani 1 1 d . . . . .
H12 H -0.0325 0.2246 0.1313 0.027 Uiso 1 1 calc R . . . .
C13 C 0.0933(3) 0.15475(12) -0.00429(11) 0.0291(3) Uani 1 1 d . . . . .
H13 H -0.0452 0.0986 -0.0412 0.035 Uiso 1 1 calc R . . . .
C14 C 0.2878(3) 0.16219(14) -0.05334(12) 0.0348(3) Uani 1 1 d . . . . .
H14 H 0.2825 0.1111 -0.1235 0.042 Uiso 1 1 calc R . . . .
C15 C 0.4882(3) 0.24412(16) 0.00036(12) 0.0367(4) Uani 1 1 d . . . . .
H15 H 0.6204 0.2500 -0.0335 0.044 Uiso 1 1 calc R . . . .
C16 C 0.4982(2) 0.31874(13) 0.10448(11) 0.0268(3) Uani 1 1 d . . . . .
H16 H 0.6373 0.3745 0.1412 0.032 Uiso 1 1 calc R . . . .
C17 C 0.1573(2) 0.47573(10) 0.26264(10) 0.0177(2) Uani 1 1 d . . . . .
C18 C 0.0403(2) 0.50339(11) 0.34992(10) 0.0201(2) Uani 1 1 d . . . . .
H18 H 0.0547 0.4654 0.4133 0.024 Uiso 1 1 calc R . . . .
C19 C -0.0979(2) 0.58628(11) 0.34558(11) 0.0225(2) Uani 1 1 d . . . . .
H19 H -0.1750 0.6048 0.4063 0.027 Uiso 1 1 calc R . . . .
C20 C -0.1232(2) 0.64161(12) 0.25300(11) 0.0251(3) Uani 1 1 d . . . . .
H20 H -0.2184 0.6973 0.2496 0.030 Uiso 1 1 calc R . . . .
C21 C -0.0071(3) 0.61452(13) 0.16520(12) 0.0298(3) Uani 1 1 d . . . . .
H21 H -0.0237 0.6518 0.1015 0.036 Uiso 1 1 calc R . . . .
C22 C 0.1333(2) 0.53298(12) 0.17026(11) 0.0259(3) Uani 1 1 d . . . . .
H22 H 0.2134 0.5162 0.1104 0.031 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
S C5 1.6905(14) . ?
S C8 1.6768(16) . ?
C6' C5 1.6905(14) . ?
C6' C8 1.6768(16) . ?
N C1 1.4765(14) . ?
N C2 1.2819(15) . ?
C1 C11 1.5229(16) . ?
C1 C17 1.5277(16) . ?
C2 C3 1.4545(16) . ?
C3 C4 1.3481(16) . ?
C4 C5 1.4531(17) . ?
C5 C6 1.5033(14) . ?
C5 S' 1.5033(14) . ?
C6 C7 1.4163(19) . ?
S' C7 1.4163(19) . ?
C7 C8 1.349(2) . ?
C11 C12 1.3978(17) . ?
C11 C16 1.3894(17) . ?
C12 C13 1.3923(19) . ?
C13 C14 1.392(2) . ?
C14 C15 1.379(2) . ?
C15 C16 1.4006(19) . ?
C17 C18 1.3934(16) . ?
C17 C22 1.4002(16) . ?
C18 C19 1.3983(17) . ?
C19 C20 1.3890(18) . ?
C20 C21 1.3932(19) . ?
C21 C22 1.3956(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 S C5 94.03(7) . . ?
C8 C6' C5 94.03(7) . . ?
C2 N C1 117.20(10) . . ?
N C1 C11 107.54(9) . . ?
N C1 C17 110.28(9) . . ?
C11 C1 C17 112.40(9) . . ?
N C2 C3 120.50(11) . . ?
C4 C3 C2 123.70(12) . . ?
C3 C4 C5 124.69(12) . . ?
C4 C5 S 123.17(9) . . ?
C4 C5 C6' 123.17(9) . . ?
C4 C5 C6 126.76(11) . . ?
C4 C5 S' 126.76(11) . . ?
C6 C5 S 109.97(8) . . ?
S' C5 C6' 109.97(8) . . ?
C7 C6 C5 107.87(10) . . ?
C7 S' C5 107.87(10) . . ?
C8 C7 C6 115.32(12) . . ?
C8 C7 S' 115.32(12) . . ?
C7 C8 S 112.81(11) . . ?
C7 C8 C6' 112.81(11) . . ?
C12 C11 C1 119.95(11) . . ?
C16 C11 C1 120.87(11) . . ?
C16 C11 C12 119.16(11) . . ?
C13 C12 C11 120.34(13) . . ?
C14 C13 C12 120.18(13) . . ?
C15 C14 C13 119.66(13) . . ?
C14 C15 C16 120.50(14) . . ?
C11 C16 C15 120.14(13) . . ?
C18 C17 C1 120.89(10) . . ?
C18 C17 C22 118.40(11) . . ?
C22 C17 C1 120.66(10) . . ?
C17 C18 C19 120.92(11) . . ?
C20 C19 C18 120.34(11) . . ?
C19 C20 C21 119.21(12) . . ?
C20 C21 C22 120.44(12) . . ?
C21 C22 C17 120.68(12) . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1 0 -1 0.1922 1.0000 -0.0013 -0.9991 0.0001 -0.0975 0.0786
0 -1 -1 0.0682 -0.0003 -1.0015 -0.9998 0.0457 0.0451 0.0711
0 1 2 0.0799 0.0005 1.0028 1.9994 -0.0348 -0.0669 -0.1261
-3 -11 -6 0.0726 -3.0036 -11.0096 -6.0009 0.5248 0.7444 0.4356
-1 0 1 0.1680 -1.0000 0.0013 0.9991 -0.0001 0.0975 -0.0786
0 0 1 0.1379 0.0001 0.0013 0.9997 0.0110 -0.0218 -0.0551
0 0 -1 0.1223 -0.0001 -0.0013 -0.9997 -0.0110 0.0218 0.0551
0 5 -4 0.1595 0.0007 4.9953 -3.9982 -0.3274 -0.0289 0.1403
0 -5 4 0.2039 -0.0007 -4.9953 3.9982 0.3274 0.0289 -0.1403

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
