# Electronic Supplementary Material (ESI) for ChemComm.
# 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_xstr0256
_database_code_depnum_ccdc_archive 'CCDC 1038092'
_audit_update_record             
;
2014-12-08 deposited with the CCDC.
2015-02-13 downloaded from the CCDC.
;
_audit_creation_date             2014-07-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4709)
;
_chemical_formula_moiety         'C25 H24 N2 O'
_chemical_formula_sum            'C25 H24 N2 O'
_chemical_formula_weight         368.48
_chemical_oxdiff_formula         'C25 H26 N2 O1'
_chemical_oxdiff_usercomment     SK413
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'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 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'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'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'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 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'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      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

_symmetry_Int_Tables_number      2
_cell_length_a                   9.4910(4)
_cell_length_b                   9.5574(3)
_cell_length_c                   10.9648(4)
_cell_angle_alpha                91.766(3)
_cell_angle_beta                 93.926(3)
_cell_angle_gamma                97.631(3)
_cell_volume                     982.69(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5260
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.7450
_cell_measurement_theta_min      5.9900
_exptl_absorpt_coefficient_mu    0.593
_exptl_absorpt_correction_T_max  0.516
_exptl_absorpt_correction_T_min  0.362
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.2452
_exptl_crystal_description       block
_exptl_crystal_F_000             393.1307
_exptl_crystal_size_max          0.5911
_exptl_crystal_size_mid          0.4497
_exptl_crystal_size_min          0.3462
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6341
_diffrn_reflns_theta_full        74.0294
_diffrn_reflns_theta_max         74.03
_diffrn_reflns_theta_min         5.99
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 5.2031
_diffrn_measured_fraction_theta_full 0.9323
_diffrn_measured_fraction_theta_max 0.9323
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -48.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000    0.0000 80

#__ type_ start__ end____ width___ exp.time_
  2 omega -116.00   -6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -19.0000 -180.0000 110

#__ type_ start__ end____ width___ exp.time_
  3 omega   27.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.2890 -130.0000 -130.0000 33

#__ type_ start__ end____ width___ exp.time_
  4 omega    9.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.2890  -99.0000   90.0000 74

#__ type_ start__ end____ width___ exp.time_
  5 omega   72.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.2890 -130.0000 -130.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   30.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -94.0000 -180.0000 72

#__ type_ start__ end____ width___ exp.time_
  7 omega   33.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -30.0000   30.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega   35.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -30.0000 -120.0000 54

#__ type_ start__ end____ width___ exp.time_
  9 omega  129.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441   30.0000  -60.0000 49

#__ type_ start__ end____ width___ exp.time_
 10 omega   86.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441   30.0000  -60.0000 29

#__ type_ start__ end____ width___ exp.time_
 11 omega   95.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  125.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega  138.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  125.0000  120.0000 38

#__ type_ start__ end____ width___ exp.time_
 13 omega   34.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -30.0000  -60.0000 54

#__ type_ start__ end____ width___ exp.time_
 14 omega   37.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -94.0000   60.0000 45

#__ type_ start__ end____ width___ exp.time_
 15 omega   63.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -94.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 16 omega   33.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -30.0000  120.0000 47

#__ type_ start__ end____ width___ exp.time_
 17 omega  110.00  169.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441   45.0000 -150.0000 59

#__ type_ start__ end____ width___ exp.time_
 18 omega   40.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -45.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
 19 omega  138.00  173.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  125.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 20 omega   83.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441 -125.0000  120.0000 34
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1540797000
_diffrn_orient_matrix_UB_12      0.0308117000
_diffrn_orient_matrix_UB_13      0.0103842000
_diffrn_orient_matrix_UB_21      0.0217225000
_diffrn_orient_matrix_UB_22      -0.0009658000
_diffrn_orient_matrix_UB_23      0.1404861000
_diffrn_orient_matrix_UB_31      0.0524609000
_diffrn_orient_matrix_UB_32      0.1598171000
_diffrn_orient_matrix_UB_33      0.0046404000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                3441
_reflns_number_total             3716
_reflns_odcompleteness_completeness 96.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_threshold_expression     I>=2u(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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.2037
_refine_diff_density_min         -0.1514
_refine_diff_density_rms         0.0311
_refine_ls_d_res_high            0.8019
_refine_ls_d_res_low             7.3915
_refine_ls_goodness_of_fit_ref   1.0610
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    42
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3716
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.0610
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0553P)²+0.1700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1069
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C3(H3a,H3b), C4(H4a,H4b), C5(H5a,H5b)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C17(H17), C18(H18),
 C20(H20), C21(H21), C22(H22), C23(H23), C25(H25)
2.c Idealised Me refined as rotating group:
 C6(H6a,H6b,H6c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
O1 O 0.37167(8) 0.67664(9) 0.45774(7) 0.0374(2) Uani 1.000000 .
N1 N 0.61290(9) 0.71147(9) 0.48174(8) 0.0274(2) Uani 1.000000 .
N2 N 0.74653(9) 0.96633(9) 0.40639(8) 0.0287(2) Uani 1.000000 .
C1 C 0.48617(11) 0.68079(11) 0.41198(10) 0.0293(2) Uani 1.000000 .
C2 C 0.49622(11) 0.65059(12) 0.27686(10) 0.0332(3) Uani 1.000000 .
C3 C 0.35863(11) 0.66613(12) 0.20127(10) 0.0316(2) Uani 1.000000 .
C4 C 0.36854(12) 0.63718(12) 0.06534(10) 0.0350(3) Uani 1.000000 .
C5 C 0.23260(13) 0.65550(13) -0.01145(11) 0.0402(3) Uani 1.000000 .
C6 C 0.24403(17) 0.62495(18) -0.14664(13) 0.0591(4) Uani 1.000000 .
C7 C 0.74929(10) 0.71776(11) 0.43074(9) 0.0271(2) Uani 1.000000 .
C8 C 0.81516(11) 0.59977(12) 0.42121(10) 0.0321(2) Uani 1.000000 .
C9 C 0.95461(12) 0.61002(13) 0.38028(10) 0.0351(3) Uani 1.000000 .
C10 C 1.02440(11) 0.73687(13) 0.35043(10) 0.0342(3) Uani 1.000000 .
C11 C 0.95738(10) 0.86030(12) 0.35707(9) 0.0290(2) Uani 1.000000 .
C12 C 1.02412(11) 0.99460(13) 0.32735(10) 0.0342(3) Uani 1.000000 .
C13 C 0.95284(12) 1.10837(12) 0.33777(10) 0.0357(3) Uani 1.000000 .
C14 C 0.81383(11) 1.08934(12) 0.37793(10) 0.0323(2) Uani 1.000000 .
C15 C 0.81741(10) 0.85184(11) 0.39724(8) 0.0261(2) Uani 1.000000 .
C17 C 0.54232(11) 0.87407(11) 0.63915(10) 0.0293(2) Uani 1.000000 .
C18 C 0.55671(11) 0.92902(11) 0.75645(10) 0.0315(2) Uani 1.000000 .
C19 C 0.64896(11) 0.87862(11) 0.84715(10) 0.0306(2) Uani 1.000000 .
C20 C 0.67352(12) 0.93987(13) 0.96747(10) 0.0378(3) Uani 1.000000 .
C21 C 0.76561(14) 0.89012(14) 1.05147(11) 0.0445(3) Uani 1.000000 .
C22 C 0.83827(14) 0.77641(15) 1.01973(11) 0.0458(3) Uani 1.000000 .
C23 C 0.81764(13) 0.71510(13) 0.90450(11) 0.0386(3) Uani 1.000000 .
C24 C 0.72284(11) 0.76425(11) 0.81508(10) 0.0301(2) Uani 1.000000 .
C25 C 0.70315(11) 0.70642(11) 0.69345(10) 0.0290(2) Uani 1.000000 .
C26 C 0.61742(10) 0.76144(11) 0.60723(9) 0.0267(2) Uani 1.000000 .
H25 H 0.74912(11) 0.63013(11) 0.67205(10) 0.0348(3) Uiso 1.000000 R
H23 H 0.86634(13) 0.64029(13) 0.88450(11) 0.0463(3) Uiso 1.000000 R
H22 H 0.90058(14) 0.74291(15) 1.07749(11) 0.0549(4) Uiso 1.000000 R
H21 H 0.78044(14) 0.93148(14) 1.12998(11) 0.0534(4) Uiso 1.000000 R
H20 H 0.62624(12) 1.01499(13) 0.98949(10) 0.0453(3) Uiso 1.000000 R
H18 H 0.50484(11) 1.00109(11) 0.77731(10) 0.0378(3) Uiso 1.000000 R
H17 H 0.48341(11) 0.91051(11) 0.58042(10) 0.0351(3) Uiso 1.000000 R
H2a H 0.57362(11) 0.71501(12) 0.24819(10) 0.0399(3) Uiso 1.000000 R
H2b H 0.51838(11) 0.55517(12) 0.26467(10) 0.0399(3) Uiso 1.000000 R
H3a H 0.28145(11) 0.60112(12) 0.22956(10) 0.0379(3) Uiso 1.000000 R
H3b H 0.33606(11) 0.76128(12) 0.21414(10) 0.0379(3) Uiso 1.000000 R
H4a H 0.44719(12) 0.70076(12) 0.03761(10) 0.0420(3) Uiso 1.000000 R
H4b H 0.38921(12) 0.54134(12) 0.05247(10) 0.0420(3) Uiso 1.000000 R
H5a H 0.15365(13) 0.59243(13) 0.01642(11) 0.0482(3) Uiso 1.000000 R
H5b H 0.21228(13) 0.75159(13) 0.00052(11) 0.0482(3) Uiso 1.000000 R
H6a H 0.1564(5) 0.6380(13) -0.19126(18) 0.0887(6) Uiso 1.000000 GR
H6b H 0.3209(8) 0.6883(9) -0.1751(3) 0.0887(6) Uiso 1.000000 GR
H6c H 0.2620(13) 0.5292(4) -0.15923(18) 0.0887(6) Uiso 1.000000 GR
H8 H 0.76865(11) 0.51267(12) 0.44154(10) 0.0385(3) Uiso 1.000000 R
H9 H 0.99890(12) 0.52923(13) 0.37375(10) 0.0421(3) Uiso 1.000000 R
H10 H 1.11663(11) 0.74235(13) 0.32555(10) 0.0411(3) Uiso 1.000000 R
H12 H 1.11584(11) 1.00519(13) 0.30093(10) 0.0411(3) Uiso 1.000000 R
H13 H 0.99528(12) 1.19759(12) 0.31864(10) 0.0428(3) Uiso 1.000000 R
H14 H 0.76681(11) 1.16830(12) 0.38474(10) 0.0388(3) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2242(13) .
N1 C1 1.3727(13) .
N1 C7 1.4396(12) .
N1 C26 1.4385(13) .
N2 C14 1.3183(14) .
N2 C15 1.3631(13) .
C1 C2 1.5126(15) .
C2 C3 1.5248(14) .
C3 C4 1.5190(15) .
C4 C5 1.5247(15) .
C5 C6 1.5160(19) .
C7 C8 1.3647(15) .
C7 C15 1.4270(15) .
C8 C9 1.4185(15) .
C9 C10 1.3626(17) .
C10 C11 1.4149(15) .
C11 C12 1.4117(16) .
C11 C15 1.4210(13) .
C12 C13 1.3606(16) .
C13 C14 1.4100(15) .
C17 C18 1.3653(15) .
C17 C26 1.4156(14) .
C18 C19 1.4178(15) .
C19 C20 1.4183(15) .
C19 C24 1.4226(15) .
C20 C21 1.3658(18) .
C21 C22 1.4094(19) .
C22 C23 1.3667(17) .
C23 C24 1.4182(15) .
C24 C25 1.4185(15) .
C25 C26 1.3680(14) .

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
C7 N1 C1 122.74(8) . .
C26 N1 C1 121.34(8) . .
C26 N1 C7 115.22(8) . .
C15 N2 C14 117.35(9) . .
N1 C1 O1 121.35(10) . .
C2 C1 O1 122.23(9) . .
C2 C1 N1 116.41(9) . .
C3 C2 C1 112.45(9) . .
C4 C3 C2 112.69(9) . .
C5 C4 C3 113.14(9) . .
C6 C5 C4 112.38(11) . .
C8 C7 N1 120.69(9) . .
C15 C7 N1 118.30(9) . .
C15 C7 C8 120.90(9) . .
C9 C8 C7 119.98(10) . .
C10 C9 C8 120.75(10) . .
C11 C10 C9 120.39(10) . .
C12 C11 C10 123.02(9) . .
C15 C11 C10 119.59(10) . .
C15 C11 C12 117.38(10) . .
C13 C12 C11 119.30(10) . .
C14 C13 C12 119.19(10) . .
C13 C14 N2 123.94(10) . .
C7 C15 N2 118.83(9) . .
C11 C15 N2 122.83(9) . .
C11 C15 C7 118.34(9) . .
C26 C17 C18 119.76(9) . .
C19 C18 C17 121.45(10) . .
C20 C19 C18 122.75(10) . .
C24 C19 C18 118.56(10) . .
C24 C19 C20 118.67(10) . .
C21 C20 C19 120.96(11) . .
C22 C21 C20 120.32(11) . .
C23 C22 C21 120.35(11) . .
C24 C23 C22 120.77(11) . .
C23 C24 C19 118.94(10) . .
C25 C24 C19 118.89(9) . .
C25 C24 C23 122.12(10) . .
C26 C25 C24 120.84(10) . .
C17 C26 N1 120.04(9) . .
C25 C26 N1 119.37(9) . .
C25 C26 C17 120.41(9) . .

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
6 0 1 0.1731 6.0000 -0.0000 1.0000 -0.9141 0.2708 0.3194
-6 0 -1 0.1731 -6.0000 0.0000 -1.0000 0.9141 -0.2708 -0.3194
1 -6 0 0.3098 1.0000 -6.0000 0.0000 -0.3389 0.0275 -0.9064
-2 -4 5 0.2634 -2.0000 -4.0000 5.0000 0.2368 0.6628 -0.7210
2 4 -5 0.2634 2.0000 4.0000 -5.0000 -0.2368 -0.6628 0.7210
-4 -4 0 0.2910 -4.0000 -4.0000 0.0000 0.4931 -0.0830 -0.8491
3 5 0 0.2268 3.0000 5.0000 -0.0000 -0.3082 0.0603 0.9565
0 6 0 0.2522 0.0000 6.0000 -0.0000 0.1849 -0.0058 0.9589
5 -4 1 0.2656 5.0000 -4.0000 1.0000 -0.8833 0.2530 -0.3723
1 0 -7 0.1412 1.0000 0.0000 -7.0000 -0.2268 -0.9617 0.0200
-1 0 7 0.3085 -1.0000 -0.0000 7.0000 0.2268 0.9617 -0.0200
-2 -5 4 0.2296 -2.0000 -5.0000 4.0000 0.1956 0.5233 -0.8854
1 5 3 0.2817 1.0000 5.0000 3.0000 0.0311 0.4384 0.8655
-1 -2 7 0.2715 -1.0000 -2.0000 7.0000 0.1651 0.9636 -0.3396

####################################################################### 
# 
# 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_xstr0259
_database_code_depnum_ccdc_archive 'CCDC 1038093'
_audit_update_record             
;
2014-12-08 deposited with the CCDC.
2015-02-13 downloaded from the CCDC.
;
_audit_creation_date             2014-07-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4709)
;
_chemical_formula_moiety         'C19 H20 N2 O S'
_chemical_formula_sum            'C19 H20 N2 O S'
_chemical_formula_weight         324.45
_chemical_oxdiff_formula         'S1 N2 O1 C19 H20'
_chemical_oxdiff_usercomment     SK415
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'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 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'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'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'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'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'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 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'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

_symmetry_Int_Tables_number      14
_cell_length_a                   16.8737(3)
_cell_length_b                   9.68667(17)
_cell_length_c                   10.28958(19)
_cell_angle_alpha                90
_cell_angle_beta                 96.9165(17)
_cell_angle_gamma                90
_cell_volume                     1669.59(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4151
_cell_measurement_temperature    150.02(10)
_cell_measurement_theta_max      73.9460
_cell_measurement_theta_min      6.6130
_exptl_absorpt_coefficient_mu    1.759
_exptl_absorpt_correction_T_max  0.632
_exptl_absorpt_correction_T_min  0.573
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2907
_exptl_crystal_description       block
_exptl_crystal_F_000             691.1676
_exptl_crystal_size_max          0.3156
_exptl_crystal_size_mid          0.2639
_exptl_crystal_size_min          0.2395
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6145
_diffrn_reflns_theta_full        74.1793
_diffrn_reflns_theta_max         74.18
_diffrn_reflns_theta_min         5.27
_diffrn_ambient_temperature      150.02(10)
_diffrn_detector_area_resol_mean 5.2031
_diffrn_measured_fraction_theta_full 0.9491
_diffrn_measured_fraction_theta_max 0.9485
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -47.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   30.0000  -90.0000 82

#__ type_ start__ end____ width___ exp.time_
  2 omega -105.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000  120.0000 90

#__ type_ start__ end____ width___ exp.time_
  3 omega    8.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.2890  -99.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega   84.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.2890   19.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   33.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -30.0000    0.0000 35

#__ type_ start__ end____ width___ exp.time_
  6 omega   88.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441   30.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega   49.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -94.0000  150.0000 59

#__ type_ start__ end____ width___ exp.time_
  8 omega   43.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -45.0000  150.0000 45

#__ type_ start__ end____ width___ exp.time_
  9 omega   38.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -45.0000  -60.0000 60

#__ type_ start__ end____ width___ exp.time_
 10 omega   89.00  172.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441   45.0000 -120.0000 83

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -30.0000   60.0000 36

#__ type_ start__ end____ width___ exp.time_
 12 omega   35.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -30.0000  120.0000 27
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0473475000
_diffrn_orient_matrix_UB_12      -0.0479526000
_diffrn_orient_matrix_UB_13      0.1108611000
_diffrn_orient_matrix_UB_21      0.0774630000
_diffrn_orient_matrix_UB_22      -0.0561622000
_diffrn_orient_matrix_UB_23      0.0763335000
_diffrn_orient_matrix_UB_31      0.0146249000
_diffrn_orient_matrix_UB_32      0.1408172000
_diffrn_orient_matrix_UB_33      0.0681188000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              20
_reflns_limit_h_min              -20
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2886
_reflns_number_total             3226
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_threshold_expression     I>=2u(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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.3723
_refine_diff_density_min         -0.2990
_refine_diff_density_rms         0.0546
_refine_ls_d_res_high            0.8013
_refine_ls_d_res_low             8.3855
_refine_ls_goodness_of_fit_ref   1.0519
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.0519
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0754P)²+0.3280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1232
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C3(H3a,H3b), C4(H4a,H4b), C5(H5a,H5b)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17),
 C18(H18)
2.c Idealised Me refined as rotating group:
 C6(H6a,H6b,H6c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
S1 S 0.88010(2) 0.25738(4) 0.76339(4) 0.03298(16) Uani 1.000000 .
O1 O 0.76843(7) 0.29812(12) 0.56543(11) 0.0349(3) Uani 1.000000 .
N1 N 0.82597(7) 0.08919(12) 0.55400(11) 0.0218(3) Uani 1.000000 .
N2 N 0.72100(7) -0.09265(13) 0.65046(12) 0.0259(3) Uani 1.000000 .
C1 C 0.76813(9) 0.18527(15) 0.51330(14) 0.0245(3) Uani 1.000000 .
C2 C 0.70598(9) 0.14357(15) 0.40155(14) 0.0260(3) Uani 1.000000 .
C3 C 0.65823(10) 0.26639(15) 0.34233(15) 0.0277(3) Uani 1.000000 .
C4 C 0.59339(10) 0.22415(17) 0.23368(16) 0.0297(3) Uani 1.000000 .
C5 C 0.54448(11) 0.34636(19) 0.17704(17) 0.0389(4) Uani 1.000000 .
C6 C 0.48135(11) 0.3079(2) 0.06432(17) 0.0445(5) Uani 1.000000 .
C7 C 0.88218(8) 0.11273(14) 0.66509(13) 0.0223(3) Uani 1.000000 .
C8 C 0.94177(9) 0.02448(16) 0.71281(14) 0.0267(3) Uani 1.000000 .
C9 C 0.98566(9) 0.07291(17) 0.83004(15) 0.0309(3) Uani 1.000000 .
C10 C 0.95887(10) 0.19556(18) 0.86927(15) 0.0347(4) Uani 1.000000 .
C11 C 0.82142(8) -0.05165(14) 0.50925(13) 0.0224(3) Uani 1.000000 .
C12 C 0.86969(9) -0.09700(16) 0.42097(14) 0.0265(3) Uani 1.000000 .
C13 C 0.87114(11) -0.23841(16) 0.38667(16) 0.0314(4) Uani 1.000000 .
C14 C 0.82446(10) -0.33152(16) 0.44282(15) 0.0317(4) Uani 1.000000 .
C15 C 0.77299(9) -0.28670(15) 0.53312(15) 0.0273(3) Uani 1.000000 .
C16 C 0.72271(10) -0.37726(16) 0.59415(17) 0.0349(4) Uani 1.000000 .
C17 C 0.67441(10) -0.32509(18) 0.67888(18) 0.0375(4) Uani 1.000000 .
C18 C 0.67539(10) -0.18199(18) 0.70315(16) 0.0324(4) Uani 1.000000 .
C19 C 0.77010(8) -0.14448(14) 0.56620(13) 0.0225(3) Uani 1.000000 .
H12 H 0.90189(9) -0.03455(16) 0.38301(14) 0.0318(4) Uiso 1.000000 R
H13 H 0.90391(11) -0.26823(16) 0.32580(16) 0.0376(4) Uiso 1.000000 R
H14 H 0.82662(10) -0.42462(16) 0.42145(15) 0.0380(4) Uiso 1.000000 R
H16 H 0.72276(10) -0.47140(16) 0.57642(17) 0.0418(5) Uiso 1.000000 R
H17 H 0.64127(10) -0.38301(18) 0.72012(18) 0.0451(5) Uiso 1.000000 R
H18 H 0.64142(10) -0.14814(18) 0.76045(16) 0.0389(4) Uiso 1.000000 R
H2a H 0.73229(9) 0.09890(15) 0.33405(14) 0.0312(4) Uiso 1.000000 R
H2b H 0.66976(9) 0.07724(15) 0.43328(14) 0.0312(4) Uiso 1.000000 R
H3a H 0.63377(10) 0.31333(15) 0.41064(15) 0.0332(4) Uiso 1.000000 R
H3b H 0.69420(10) 0.33090(15) 0.30738(15) 0.0332(4) Uiso 1.000000 R
H4a H 0.61796(10) 0.17930(17) 0.16433(16) 0.0356(4) Uiso 1.000000 R
H4b H 0.55818(10) 0.15787(17) 0.26805(16) 0.0356(4) Uiso 1.000000 R
H5a H 0.51840(11) 0.38881(19) 0.24597(17) 0.0467(5) Uiso 1.000000 R
H5b H 0.58019(11) 0.41428(19) 0.14642(17) 0.0467(5) Uiso 1.000000 R
H6a H 0.50699(11) 0.2757(14) -0.0084(5) 0.0667(7) Uiso 1.000000 GR
H6b H 0.4479(6) 0.2362(11) 0.0920(5) 0.0667(7) Uiso 1.000000 GR
H6c H 0.4494(6) 0.3875(4) 0.0383(9) 0.0667(7) Uiso 1.000000 GR
H8 H 0.95240(9) -0.05841(16) 0.67273(14) 0.0321(4) Uiso 1.000000 R
H9 H 1.02831(9) 0.02533(17) 0.87509(15) 0.0370(4) Uiso 1.000000 R
H10 H 0.98048(10) 0.24136(18) 0.94476(15) 0.0417(4) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C7 1.7310(14) .
S1 C10 1.7215(17) .
O1 C1 1.2174(19) .
N1 C1 1.3768(18) .
N1 C7 1.4132(17) .
N1 C11 1.4389(17) .
N2 C18 1.318(2) .
N2 C19 1.3649(19) .
C1 C2 1.5147(19) .
C2 C3 1.522(2) .
C3 C4 1.523(2) .
C4 C5 1.519(2) .
C5 C6 1.524(2) .
C7 C8 1.365(2) .
C8 C9 1.417(2) .
C9 C10 1.350(2) .
C11 C12 1.364(2) .
C11 C19 1.423(2) .
C12 C13 1.415(2) .
C13 C14 1.370(2) .
C14 C15 1.414(2) .
C15 C16 1.418(2) .
C15 C19 1.421(2) .
C16 C17 1.360(3) .
C17 C18 1.408(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
C10 S1 C7 91.13(7) . .
C7 N1 C1 121.27(12) . .
C11 N1 C1 122.34(12) . .
C11 N1 C7 114.62(11) . .
C19 N2 C18 116.69(13) . .
N1 C1 O1 120.51(13) . .
C2 C1 O1 122.66(13) . .
C2 C1 N1 116.82(12) . .
C3 C2 C1 112.34(12) . .
C4 C3 C2 112.50(12) . .
C5 C4 C3 112.42(14) . .
C6 C5 C4 113.53(16) . .
N1 C7 S1 122.98(11) . .
C8 C7 S1 111.26(11) . .
C8 C7 N1 125.69(13) . .
C9 C8 C7 112.68(14) . .
C10 C9 C8 112.72(14) . .
C9 C10 S1 112.19(12) . .
C12 C11 N1 120.36(13) . .
C19 C11 N1 118.63(12) . .
C19 C11 C12 120.85(13) . .
C13 C12 C11 120.50(15) . .
C14 C13 C12 120.25(15) . .
C15 C14 C13 120.30(14) . .
C16 C15 C14 123.25(14) . .
C19 C15 C14 119.76(14) . .
C19 C15 C16 116.99(15) . .
C17 C16 C15 119.36(15) . .
C18 C17 C16 118.96(15) . .
C17 C18 N2 124.65(15) . .
C11 C19 N2 118.38(13) . .
C15 C19 N2 123.34(13) . .
C15 C19 C11 118.29(13) . .

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
-6 4 -3 0.1691 -6.0000 4.0000 -3.0000 -0.2403 -0.9184 0.2712
6 -4 3 0.1691 6.0000 -4.0000 3.0000 0.2403 0.9184 -0.2712
-1 -6 -3 0.1278 -1.0001 -6.0000 -3.0000 0.0025 0.0305 -1.0639
1 6 3 0.1278 1.0001 6.0000 3.0000 -0.0025 -0.0305 1.0639
8 3 -3 0.1197 8.0000 3.0000 -3.0000 -0.8552 0.2222 0.3351
-8 -3 3 0.1197 -8.0000 -3.0000 3.0000 0.8552 -0.2222 -0.3351
-8 -1 5 0.1027 -7.9999 -1.0000 5.0000 0.9810 -0.1819 0.0828
5 -3 -5 0.1406 4.9999 -3.0000 -5.0000 -0.6472 0.1741 -0.6899
6 1 5 0.1364 6.0001 1.0000 5.0000 0.2223 0.7903 0.5692
-5 6 -1 0.1140 -4.9999 6.0000 -1.0000 -0.1618 -0.8006 0.7037
-2 -5 -4 0.1238 -2.0001 -5.0000 -4.0000 -0.1090 -0.1795 -1.0058
-7 0 -5 0.1254 -7.0001 -0.0000 -5.0000 -0.2229 -0.9239 -0.4430
-5 5 -2 0.0888 -5.0000 5.0000 -2.0000 -0.2247 -0.8208 0.4947
-7 3 -3 0.0833 -7.0000 3.0000 -3.0000 -0.1450 -0.9397 0.1157

