# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

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

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 N2 O2 S2'
_chemical_formula_weight         384.50

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

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   5.215(5)
_cell_length_b                   23.832(5)
_cell_length_c                   14.377(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 95.528(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1778.5(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13705
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_sigmaI/netI    0.0635
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3124
_reflns_number_gt                2495
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlisPro RED (Oxford Diffraction, 2009)'
_computing_structure_solution    'SHELXS97  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0113P)²+6.2389P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3124
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0689
_refine_ls_wR_factor_ref         0.1495
_refine_ls_wR_factor_gt          0.1437
_refine_ls_goodness_of_fit_ref   1.229
_refine_ls_restrained_S_all      1.229
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S -0.7478(2) 0.25143(5) -0.25110(8) 0.0209(3) Uani 1 1 d . . .
S1A S 0.3051(3) 0.13492(6) 0.16532(10) 0.0182(6) Uani 0.701(16) 1 d P A 1
C21A C 0.3051(3) 0.13492(6) 0.16532(10) 0.0182(6) Uani 0.31(5) 1 d P A 1
H1A H 0.3246 0.1731 0.1545 0.022 Uiso 0.31(5) 1 calc PR A 1
S1B S 0.1524(5) 0.02866(11) 0.16754(18) 0.0240(11) Uani 0.299(16) 1 d P A 2
C21B C 0.1524(5) 0.02866(11) 0.16754(18) 0.0240(11) Uani 0.69(5) 1 d P A 2
H1B H 0.0631 -0.0049 0.1569 0.029 Uiso 0.69(5) 1 calc PR A 2
O1 O 0.0609(6) 0.23597(12) 0.0334(2) 0.0183(7) Uani 1 1 d . . .
O2 O -0.6677(6) 0.05211(12) -0.0820(2) 0.0171(7) Uani 1 1 d . . .
N2 N -0.3009(7) 0.06009(15) 0.0220(2) 0.0146(8) Uani 1 1 d . . .
H2 H -0.2959 0.0258 0.0405 0.018 Uiso 1 1 calc R . .
C15 C -0.1226(8) 0.10056(18) 0.0549(3) 0.0132(9) Uani 1 1 d . A .
C13 C -0.4198(8) 0.13946(18) -0.0545(3) 0.0149(9) Uani 1 1 d . A .
C4 C -1.0224(9) 0.22210(19) -0.3046(3) 0.0200(10) Uani 1 1 d . . .
H4 H -1.1250 0.2389 -0.3533 0.024 Uiso 1 1 calc R . .
C6 C -0.4844(8) 0.18826(18) -0.1040(3) 0.0127(9) Uani 1 1 d . . .
N1 N -0.3058(7) 0.22890(14) -0.0731(2) 0.0144(8) Uani 1 1 d . . .
C1 C -0.6956(8) 0.19488(18) -0.1757(3) 0.0150(10) Uani 1 1 d . . .
C7 C -0.2903(8) 0.28775(18) -0.1008(3) 0.0147(9) Uani 1 1 d . . .
H7A H -0.3328 0.2907 -0.1678 0.018 Uiso 1 1 calc R . .
H7B H -0.1146 0.3008 -0.0867 0.018 Uiso 1 1 calc R . .
C12 C -0.3649(9) 0.4519(2) 0.1202(4) 0.0293(12) Uani 1 1 d . . .
H12A H -0.5338 0.4381 0.0994 0.044 Uiso 1 1 calc R . .
H12B H -0.3467 0.4895 0.0982 0.044 Uiso 1 1 calc R . .
H12C H -0.3417 0.4515 0.1872 0.044 Uiso 1 1 calc R . .
C10 C -0.1799(9) 0.4129(2) -0.0246(3) 0.0227(11) Uani 1 1 d . . .
H10A H -0.0363 0.3910 -0.0429 0.027 Uiso 1 1 calc R . .
H10B H -0.1609 0.4508 -0.0476 0.027 Uiso 1 1 calc R . .
C18 C 0.0866(8) 0.08744(19) 0.1230(3) 0.0172(10) Uani 1 1 d . . .
C17 C -0.1175(8) 0.20738(18) -0.0028(3) 0.0145(9) Uani 1 1 d . A .
C9 C -0.4316(8) 0.38796(19) -0.0722(3) 0.0188(10) Uani 1 1 d . . .
H9A H -0.5758 0.4090 -0.0521 0.023 Uiso 1 1 calc R . .
H9B H -0.4331 0.3928 -0.1392 0.023 Uiso 1 1 calc R . .
C14 C -0.4882(8) 0.08130(18) -0.0443(3) 0.0145(9) Uani 1 1 d . . .
C16 C -0.1944(8) 0.14980(18) 0.0080(3) 0.0138(9) Uani 1 1 d . . .
C2 C -0.8878(8) 0.15582(19) -0.1937(3) 0.0177(10) Uani 1 1 d . . .
H2A H -0.8952 0.1224 -0.1606 0.021 Uiso 1 1 calc R . .
C19 C 0.3800(11) 0.0383(3) 0.2281(4) 0.0364(14) Uani 1 1 d . . .
H19 H 0.4614 0.0095 0.2633 0.044 Uiso 1 1 calc R A 2
C11 C -0.1640(9) 0.4147(2) 0.0820(3) 0.0252(11) Uani 1 1 d . . .
H11A H -0.1831 0.3769 0.1052 0.030 Uiso 1 1 calc R . .
H11B H 0.0057 0.4280 0.1057 0.030 Uiso 1 1 calc R . .
C20 C 0.4704(10) 0.0902(3) 0.2319(4) 0.0369(16) Uani 1 1 d . A .
H20 H 0.576(11) 0.104(3) 0.261(4) 0.05(2) Uiso 1 1 d . . .
C8 C -0.4709(8) 0.32570(18) -0.0515(3) 0.0179(10) Uani 1 1 d . . .
H8A H -0.6478 0.3155 -0.0713 0.021 Uiso 1 1 calc R . .
H8B H -0.4420 0.3196 0.0154 0.021 Uiso 1 1 calc R . .
C3 C -1.0731(9) 0.1714(2) -0.2673(3) 0.0205(10) Uani 1 1 d . . .
H3 H -1.2143 0.1493 -0.2880 0.025 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
S2 C4 1.708(5) . ?
S2 C1 1.735(4) . ?
S1A C20 1.624(7) . ?
S1A C18 1.678(5) . ?
S1B C18 1.564(5) . ?
O1 C17 1.228(5) . ?
O2 C14 1.248(5) . ?
N2 C15 1.390(5) . ?
N2 C14 1.392(5) . ?
C15 C16 1.387(6) . ?
C15 C18 1.429(6) . ?
C13 C6 1.388(6) . ?
C13 C16 1.431(6) . ?
C13 C14 1.442(6) . ?
C4 C3 1.359(7) . ?
C6 N1 1.387(5) . ?
C6 C1 1.443(6) . ?
N1 C17 1.435(5) . ?
N1 C7 1.462(5) . ?
C1 C2 1.374(6) . ?
C7 C8 1.528(6) . ?
C12 C11 1.515(7) . ?
C10 C11 1.527(7) . ?
C10 C9 1.540(6) . ?
C17 C16 1.442(6) . ?
C9 C8 1.531(6) . ?
C2 C3 1.412(6) . ?
C19 C20 1.322(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 S2 C1 92.2(2) . . ?
C20 S1A C18 94.3(3) . . ?
C15 N2 C14 112.5(3) . . ?
C16 C15 N2 106.4(4) . . ?
C16 C15 C18 132.1(4) . . ?
N2 C15 C18 121.5(4) . . ?
C6 C13 C16 108.8(4) . . ?
C6 C13 C14 143.9(4) . . ?
C16 C13 C14 107.3(4) . . ?
C3 C4 S2 111.9(3) . . ?
N1 C6 C13 107.4(4) . . ?
N1 C6 C1 126.5(4) . . ?
C13 C6 C1 126.1(4) . . ?
C6 N1 C17 111.6(3) . . ?
C6 N1 C7 129.5(4) . . ?
C17 N1 C7 118.9(3) . . ?
C2 C1 C6 123.6(4) . . ?
C2 C1 S2 109.9(3) . . ?
C6 C1 S2 126.5(3) . . ?
N1 C7 C8 112.9(3) . . ?
C11 C10 C9 114.7(4) . . ?
C15 C18 S1B 126.8(4) . . ?
C15 C18 S1A 123.2(4) . . ?
S1B C18 S1A 109.9(3) . . ?
O1 C17 N1 122.7(4) . . ?
O1 C17 C16 133.6(4) . . ?
N1 C17 C16 103.7(3) . . ?
C8 C9 C10 114.3(4) . . ?
O2 C14 N2 122.9(4) . . ?
O2 C14 C13 132.3(4) . . ?
N2 C14 C13 104.8(4) . . ?
C15 C16 C13 109.0(4) . . ?
C15 C16 C17 142.4(4) . . ?
C13 C16 C17 108.5(4) . . ?
C1 C2 C3 113.4(4) . . ?
C12 C11 C10 114.0(4) . . ?
C19 C20 S1A 115.0(4) . . ?
C9 C8 C7 112.6(4) . . ?
C4 C3 C2 112.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.085
_database_code_depnum_ccdc_archive 'CCDC 1015521'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_red
_audit_creation_date             2013-10-23
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H24 N2 O2'
_chemical_formula_sum            'C24 H24 N2 O2'
_chemical_formula_weight         372.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H11 N3 O4 F2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.9724(13)
_cell_length_b                   26.488(6)
_cell_length_c                   14.650(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.55(2)
_cell_angle_gamma                90.00
_cell_volume                     1916.9(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    483
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      19.9380
_cell_measurement_theta_min      2.6870
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1166
_diffrn_reflns_av_unetI/netI     0.2341
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7995
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.70
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector_area_resol_mean 16.0839
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -96.00  -65.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4177  179.0000 -120.0000 31

#__ type_ start__ end____ width___ exp.time_
  2 omega  -83.00  -37.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4177  179.0000    0.0000 46

#__ type_ start__ end____ width___ exp.time_
  3 omega   13.00   43.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       21.4490  -57.0000  -90.0000 30

#__ type_ start__ end____ width___ exp.time_
  4 omega    7.00   94.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       21.4490   37.0000  -60.0000 87

#__ type_ start__ end____ width___ exp.time_
  5 omega  -50.00   -3.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       21.4490  -37.0000    0.0000 47

#__ type_ start__ end____ width___ exp.time_
  6 omega   -9.00   16.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       21.4490   77.0000   90.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0009045000
_diffrn_orient_matrix_UB_12      -0.0125895000
_diffrn_orient_matrix_UB_13      -0.0427524000
_diffrn_orient_matrix_UB_21      -0.0579338000
_diffrn_orient_matrix_UB_22      0.0216064000
_diffrn_orient_matrix_UB_23      -0.0230611000
_diffrn_orient_matrix_UB_31      0.1315230000
_diffrn_orient_matrix_UB_32      0.0095194000
_diffrn_orient_matrix_UB_33      -0.0038191000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Mova (Mo) X-ray Source'
_reflns_number_gt                1039
_reflns_number_total             3358
_reflns_odcompleteness_completeness 88.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.850
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3358
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2647
_refine_ls_R_factor_gt           0.0889
_refine_ls_restrained_S_all      0.850
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0408P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.2099
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  {H19A,H19B} of C19, {H22A,H22B} of C22, {H21A,H21B} of C21, H16 of C16, H11
  of C11, H15 of C15, H18 of C18, H17 of C17, H7 of C7, H14 of C14, H8 of C8,
  H9 of C9, {H20A,H20B} of C20, H10 of C10, {H23A,H23B} of C23
 At 1.5 times of:
  {H24A,H24B,H24C} of C24
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C20(H20A,H20B), C19(H19A,H19B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C14(H14), C7(H7), C17(H17), C18(H18), C15(H15), C11(H11), C16(H16),
 C9(H9), C10(H10)
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8593(8) 0.22631(15) 0.5864(3) 0.0523(12) Uani 1 1 d . . .
N1 N 0.4957(9) 0.21352(18) 0.4734(3) 0.0414(13) Uani 1 1 d . . .
N2 N 0.6699(11) 0.0595(2) 0.5281(3) 0.0472(15) Uani 1 1 d . . .
O2 O 0.2958(8) 0.04530(16) 0.4228(3) 0.0586(13) Uani 1 1 d . . .
C8 C 1.4023(11) 0.1246(2) 0.7496(4) 0.0445(16) Uani 1 1 d . . .
H8 H 1.4873 0.1522 0.7799 0.053 Uiso 1 1 calc R . .
C12 C 0.3512(11) 0.1732(2) 0.4328(4) 0.0400(15) Uani 1 1 d . . .
C1 C 0.7062(12) 0.1972(2) 0.5398(4) 0.0418(16) Uani 1 1 d . . .
C14 C 0.0908(11) 0.2201(2) 0.3024(4) 0.0472(17) Uani 1 1 d . . .
H14 H 0.2116 0.2469 0.3124 0.057 Uiso 1 1 calc R . .
C2 C 0.6894(12) 0.1419(2) 0.5363(4) 0.0420(16) Uani 1 1 d . . .
C5 C 0.8124(12) 0.0990(3) 0.5705(4) 0.0459(17) Uani 1 1 d . . .
C7 C 1.1819(12) 0.1316(2) 0.6839(4) 0.0465(17) Uani 1 1 d . . .
H7 H 1.1224 0.1643 0.6698 0.056 Uiso 1 1 calc R . .
C6 C 1.0478(12) 0.0914(3) 0.6385(4) 0.0456(17) Uani 1 1 d . . .
C13 C 0.1285(11) 0.1778(2) 0.3584(4) 0.0436(16) Uani 1 1 d . . .
C3 C 0.4652(11) 0.1300(2) 0.4709(4) 0.0406(16) Uani 1 1 d . . .
C17 C -0.2615(12) 0.1407(3) 0.2686(4) 0.0505(17) Uani 1 1 d . . .
H17 H -0.3751 0.1132 0.2555 0.061 Uiso 1 1 calc R . .
C18 C -0.0517(11) 0.1380(2) 0.3396(4) 0.0440(16) Uani 1 1 d . . .
H18 H -0.0315 0.1090 0.3754 0.053 Uiso 1 1 calc R . .
C15 C -0.1213(12) 0.2239(3) 0.2318(4) 0.0504(17) Uani 1 1 d . . .
H15 H -0.1413 0.2526 0.1950 0.060 Uiso 1 1 calc R . .
C11 C 1.1439(12) 0.0424(3) 0.6608(4) 0.0546(18) Uani 1 1 d . . .
H11 H 1.0566 0.0147 0.6321 0.066 Uiso 1 1 calc R . .
C4 C 0.4507(12) 0.0742(2) 0.4670(4) 0.0465(17) Uani 1 1 d . . .
C16 C -0.3007(13) 0.1842(3) 0.2176(4) 0.0550(19) Uani 1 1 d . . .
H16 H -0.4495 0.1870 0.1733 0.066 Uiso 1 1 calc R . .
C21 C 0.4914(11) 0.3578(2) 0.4414(4) 0.0474(17) Uani 1 1 d . . .
H21A H 0.5475 0.3790 0.3929 0.057 Uiso 1 1 calc R . .
H21B H 0.2955 0.3594 0.4375 0.057 Uiso 1 1 calc R . .
C22 C 0.6091(12) 0.3789(2) 0.5327(4) 0.0567(19) Uani 1 1 d . . .
H22A H 0.8046 0.3806 0.5346 0.068 Uiso 1 1 calc R . .
H22B H 0.5668 0.3564 0.5813 0.068 Uiso 1 1 calc R . .
C20 C 0.5762(12) 0.3028(2) 0.4246(4) 0.0494(17) Uani 1 1 d . . .
H20A H 0.5472 0.2953 0.3594 0.059 Uiso 1 1 calc R . .
H20B H 0.7673 0.2985 0.4451 0.059 Uiso 1 1 calc R . .
C9 C 1.4947(12) 0.0759(2) 0.7698(4) 0.0521(18) Uani 1 1 d . . .
H9 H 1.6431 0.0707 0.8134 0.062 Uiso 1 1 calc R . .
C19 C 0.4093(11) 0.2662(2) 0.4772(4) 0.0461(17) Uani 1 1 d . . .
H19A H 0.4221 0.2767 0.5409 0.055 Uiso 1 1 calc R . .
H19B H 0.2208 0.2685 0.4519 0.055 Uiso 1 1 calc R . .
C24 C 0.6364(13) 0.4560(2) 0.6350(4) 0.072(2) Uani 1 1 d . . .
H24A H 0.8272 0.4584 0.6308 0.109 Uiso 1 1 calc R . .
H24B H 0.6067 0.4360 0.6876 0.109 Uiso 1 1 calc R . .
H24C H 0.5633 0.4892 0.6413 0.109 Uiso 1 1 calc R . .
C23 C 0.4991(13) 0.4315(2) 0.5497(4) 0.064(2) Uani 1 1 d . . .
H23A H 0.5220 0.4528 0.4973 0.077 Uiso 1 1 calc R . .
H23B H 0.3067 0.4290 0.5547 0.077 Uiso 1 1 calc R . .
C10 C 1.3644(12) 0.0352(3) 0.7245(4) 0.0591(19) Uani 1 1 d . . .
H10 H 1.4275 0.0027 0.7375 0.071 Uiso 1 1 calc R . .
H2 H 0.721(10) 0.0283(19) 0.536(3) 0.034(18) Uiso 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.234(6) . ?
N1 C12 1.383(7) . ?
N1 C1 1.412(7) . ?
N1 C19 1.463(6) . ?
N2 C5 1.372(7) . ?
N2 C4 1.385(7) . ?
O2 C4 1.219(6) . ?
C8 C7 1.387(7) . ?
C8 C9 1.388(8) . ?
C12 C13 1.468(8) . ?
C12 C3 1.367(7) . ?
C1 C2 1.468(8) . ?
C14 C13 1.389(8) . ?
C14 C15 1.394(8) . ?
C2 C5 1.357(8) . ?
C2 C3 1.419(8) . ?
C5 C6 1.462(8) . ?
C7 C6 1.385(8) . ?
C6 C11 1.409(8) . ?
C13 C18 1.389(7) . ?
C3 C4 1.482(8) . ?
C17 C18 1.389(7) . ?
C17 C16 1.375(8) . ?
C15 C16 1.378(8) . ?
C11 C10 1.369(8) . ?
C21 C22 1.505(7) . ?
C21 C20 1.546(7) . ?
C22 C23 1.528(7) . ?
C20 C19 1.538(7) . ?
C9 C10 1.388(8) . ?
C24 C23 1.502(8) . ?

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
C12 N1 C1 111.6(5) . . ?
C12 N1 C19 127.7(5) . . ?
C1 N1 C19 117.7(5) . . ?
C5 N2 C4 114.0(6) . . ?
C7 C8 C9 119.2(6) . . ?
N1 C12 C13 124.6(6) . . ?
C3 C12 N1 107.4(5) . . ?
C3 C12 C13 127.9(6) . . ?
O1 C1 N1 123.4(6) . . ?
O1 C1 C2 132.3(6) . . ?
N1 C1 C2 104.3(5) . . ?
C13 C14 C15 122.4(6) . . ?
C5 C2 C1 143.1(6) . . ?
C5 C2 C3 110.6(6) . . ?
C3 C2 C1 106.3(6) . . ?
N2 C5 C6 122.4(6) . . ?
C2 C5 N2 106.4(6) . . ?
C2 C5 C6 131.2(6) . . ?
C6 C7 C8 122.0(6) . . ?
C7 C6 C5 121.7(6) . . ?
C7 C6 C11 117.6(6) . . ?
C11 C6 C5 120.6(6) . . ?
C14 C13 C12 123.0(6) . . ?
C18 C13 C12 120.0(6) . . ?
C18 C13 C14 117.0(6) . . ?
C12 C3 C2 110.4(6) . . ?
C12 C3 C4 143.5(6) . . ?
C2 C3 C4 106.1(6) . . ?
C16 C17 C18 119.9(6) . . ?
C17 C18 C13 121.5(6) . . ?
C16 C15 C14 118.6(6) . . ?
C10 C11 C6 120.7(6) . . ?
N2 C4 C3 102.9(6) . . ?
O2 C4 N2 124.8(6) . . ?
O2 C4 C3 132.3(6) . . ?
C17 C16 C15 120.5(6) . . ?
C22 C21 C20 113.9(5) . . ?
C21 C22 C23 111.9(5) . . ?
C19 C20 C21 110.0(5) . . ?
C10 C9 C8 119.7(6) . . ?
N1 C19 C20 113.9(4) . . ?
C24 C23 C22 113.1(6) . . ?
C11 C10 C9 120.7(6) . . ?
# start Validation Reply Form
_vrf_PLAT026_red                 
;
PROBLEM: Ratio Observed / Unique Reflections too Low ....         31 %     
RESPONSE: The crystal was small and weakly difracting
;
# end Validation Reply Form


_database_code_depnum_ccdc_archive 'CCDC 992180'
