# 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_TRYA2_final
_database_code_depnum_ccdc_archive 'CCDC 1056290'
_audit_update_record             
;
2015-03-26 deposited with the CCDC.
2015-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 Cl2 N2 O2'
_chemical_formula_weight         438.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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

_cell_length_a                   29.2646(12)
_cell_length_b                   9.4866(4)
_cell_length_c                   15.7986(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.661(2)
_cell_angle_gamma                90
_cell_volume                     4262.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       PLATE
_exptl_crystal_colour            PINK
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             1856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.333
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23016
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.432
_diffrn_reflns_theta_max         26.377
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4358
_reflns_number_gt                3355
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4358
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0749
_refine_ls_wR_factor_ref         0.1314
_refine_ls_wR_factor_gt          0.1293
_refine_ls_goodness_of_fit_ref   3.455
_refine_ls_restrained_S_all      3.455
_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_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
Cl01 Cl 0.90022(3) 0.70566(10) 0.13200(7) 0.0517(3) Uani 1 1 d . . . . .
Cl02 Cl 0.94564(4) 0.43525(11) 0.15897(12) 0.1106(6) Uani 1 1 d . . . . .
O2 O 0.62296(7) 0.8776(2) 0.59684(13) 0.0311(6) Uani 1 1 d . . . . .
O1 O 0.79303(7) 0.5616(2) 1.01174(13) 0.0340(6) Uani 1 1 d . . . . .
N005 N 0.78697(8) 0.5091(3) 0.86745(14) 0.0251(6) Uani 1 1 d . . . . .
N006 N 0.56490(9) 0.7216(3) 0.60493(16) 0.0344(7) Uani 1 1 d . . . . .
C007 C 0.67882(10) 0.6455(3) 0.73494(18) 0.0218(7) Uani 1 1 d . . . . .
H007 H 0.6541 0.6994 0.7449 0.026 Uiso 1 1 calc R U . . .
C008 C 0.71605(10) 0.6110(3) 0.80306(18) 0.0202(7) Uani 1 1 d . . . . .
C009 C 0.75350(10) 0.5324(3) 0.78794(18) 0.0221(7) Uani 1 1 d . . . . .
C00A C 0.64317(10) 0.6350(3) 0.48718(18) 0.0224(7) Uani 1 1 d . . . . .
C00B C 0.67845(10) 0.5989(3) 0.65051(18) 0.0213(7) Uani 1 1 d . . . . .
C00C C 0.77164(10) 0.5675(3) 0.9354(2) 0.0250(7) Uani 1 1 d . . . . .
C00D C 0.72450(10) 0.6367(3) 0.89937(18) 0.0256(7) Uani 1 1 d . . . . .
H00A H 0.7001 0.5936 0.9230 0.031 Uiso 1 1 calc R U . . .
H00B H 0.7258 0.7368 0.9123 0.031 Uiso 1 1 calc R U . . .
C00E C 0.60812(10) 0.7576(4) 0.59435(18) 0.0251(7) Uani 1 1 d . . . . .
C00F C 0.61248(11) 0.5761(3) 0.41480(19) 0.0276(8) Uani 1 1 d . . . . .
H00F H 0.5874 0.5211 0.4223 0.033 Uiso 1 1 calc R U . . .
C00G C 0.63388(10) 0.6204(3) 0.57843(18) 0.0239(7) Uani 1 1 d . . . . .
C00H C 0.71573(10) 0.5189(3) 0.63789(18) 0.0248(7) Uani 1 1 d . . . . .
H00H H 0.7152 0.4863 0.5821 0.030 Uiso 1 1 calc R U . . .
C00I C 0.75416(10) 0.4853(3) 0.70556(18) 0.0256(7) Uani 1 1 d . . . . .
H00I H 0.7793 0.4331 0.6956 0.031 Uiso 1 1 calc R U . . .
C00J C 0.67991(10) 0.7163(3) 0.47369(19) 0.0262(8) Uani 1 1 d . . . . .
H00J H 0.7005 0.7578 0.5211 0.031 Uiso 1 1 calc R U . . .
C00K C 0.59801(11) 0.5087(4) 0.58646(18) 0.0316(8) Uani 1 1 d . . . . .
C00L C 0.61889(11) 0.5987(3) 0.33164(19) 0.0303(8) Uani 1 1 d . . . . .
H00L H 0.5979 0.5597 0.2839 0.036 Uiso 1 1 calc R U . . .
C00M C 0.68666(11) 0.7370(3) 0.39089(19) 0.0295(8) Uani 1 1 d . . . . .
H00M H 0.7119 0.7909 0.3831 0.035 Uiso 1 1 calc R U . . .
C00N C 0.65585(11) 0.6777(3) 0.3193(2) 0.0320(8) Uani 1 1 d . . . . .
H00N H 0.6603 0.6916 0.2636 0.038 Uiso 1 1 calc R U . . .
C00O C 0.55879(11) 0.5754(4) 0.60316(19) 0.0366(9) Uani 1 1 d . . . . .
C00P C 0.60008(13) 0.3654(4) 0.58326(19) 0.0429(10) Uani 1 1 d . . . . .
H00P H 0.6262 0.3202 0.5719 0.051 Uiso 1 1 calc R U . . .
C00Q C 0.53046(12) 0.8243(4) 0.6193(2) 0.0517(11) Uani 1 1 d . . . . .
H00C H 0.5424 0.9178 0.6155 0.078 Uiso 1 1 calc R U . . .
H00D H 0.5247 0.8103 0.6761 0.078 Uiso 1 1 calc R U . . .
H00E H 0.5016 0.8125 0.5759 0.078 Uiso 1 1 calc R U . . .
C00R C 0.52065(13) 0.5021(5) 0.6176(2) 0.0548(12) Uani 1 1 d . . . . .
H00R H 0.4947 0.5478 0.6291 0.066 Uiso 1 1 calc R U . . .
C00S C 0.56156(17) 0.2872(5) 0.5976(2) 0.0574(12) Uani 1 1 d . . . . .
H00S H 0.5620 0.1892 0.5959 0.069 Uiso 1 1 calc R U . . .
C00T C 0.52330(16) 0.3572(6) 0.6140(2) 0.0660(15) Uani 1 1 d . . . . .
H00T H 0.4981 0.3043 0.6231 0.079 Uiso 1 1 calc R U . . .
C00U C 0.89481(13) 0.5229(4) 0.1155(3) 0.0667(13) Uani 1 1 d . . . . .
H00G H 0.8702 0.4876 0.1415 0.080 Uiso 1 1 calc R U . . .
H00K H 0.8855 0.5039 0.0534 0.080 Uiso 1 1 calc R U . . .


_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
Cl01 C00U 1.755(4) . ?
Cl02 C00U 1.701(4) . ?
O2 C00E 1.215(4) . ?
O1 C00C 1.222(3) . ?
N005 C00C 1.373(4) . ?
N005 C009 1.416(3) . ?
N006 C00E 1.358(4) . ?
N006 C00O 1.398(4) . ?
N006 C00Q 1.458(4) . ?
C007 C008 1.378(4) . ?
C007 C00B 1.403(4) . ?
C007 H007 0.9300 . ?
C008 C009 1.392(4) . ?
C008 C00D 1.503(4) . ?
C009 C00I 1.380(4) . ?
C00A C00J 1.380(4) . ?
C00A C00F 1.393(4) . ?
C00A C00G 1.535(4) . ?
C00B C00H 1.381(4) . ?
C00B C00G 1.529(4) . ?
C00C C00D 1.513(4) . ?
C00D H00A 0.9700 . ?
C00D H00B 0.9700 . ?
C00E C00G 1.554(4) . ?
C00F C00L 1.387(4) . ?
C00F H00F 0.9300 . ?
C00G C00K 1.518(4) . ?
C00H C00I 1.393(4) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00J C00M 1.382(4) . ?
C00J H00J 0.9300 . ?
C00K C00P 1.363(5) . ?
C00K C00O 1.389(5) . ?
C00L C00N 1.367(4) . ?
C00L H00L 0.9300 . ?
C00M C00N 1.388(4) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00O C00R 1.379(5) . ?
C00P C00S 1.412(5) . ?
C00P H00P 0.9300 . ?
C00Q H00C 0.9600 . ?
C00Q H00D 0.9600 . ?
C00Q H00E 0.9600 . ?
C00R C00T 1.379(6) . ?
C00R H00R 0.9300 . ?
C00S C00T 1.379(6) . ?
C00S H00S 0.9300 . ?
C00T H00T 0.9300 . ?
C00U H00G 0.9700 . ?
C00U H00K 0.9700 . ?

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
C00C N005 C009 110.2(2) . . ?
C00E N006 C00O 111.5(3) . . ?
C00E N006 C00Q 123.3(3) . . ?
C00O N006 C00Q 125.2(3) . . ?
C008 C007 C00B 119.7(3) . . ?
C008 C007 H007 120.2 . . ?
C00B C007 H007 120.2 . . ?
C007 C008 C009 120.2(3) . . ?
C007 C008 C00D 131.5(3) . . ?
C009 C008 C00D 108.2(2) . . ?
C00I C009 C008 121.5(3) . . ?
C00I C009 N005 128.7(3) . . ?
C008 C009 N005 109.8(3) . . ?
C00J C00A C00F 118.2(3) . . ?
C00J C00A C00G 120.9(3) . . ?
C00F C00A C00G 120.8(3) . . ?
C00H C00B C007 118.8(3) . . ?
C00H C00B C00G 122.0(3) . . ?
C007 C00B C00G 118.7(3) . . ?
O1 C00C N005 124.6(3) . . ?
O1 C00C C00D 126.8(3) . . ?
N005 C00C C00D 108.6(2) . . ?
C008 C00D C00C 103.1(2) . . ?
C008 C00D H00A 111.1 . . ?
C00C C00D H00A 111.1 . . ?
C008 C00D H00B 111.1 . . ?
C00C C00D H00B 111.1 . . ?
H00A C00D H00B 109.1 . . ?
O2 C00E N006 124.6(3) . . ?
O2 C00E C00G 127.3(3) . . ?
N006 C00E C00G 108.1(3) . . ?
C00A C00F C00L 120.7(3) . . ?
C00A C00F H00F 119.7 . . ?
C00L C00F H00F 119.7 . . ?
C00K C00G C00B 109.3(2) . . ?
C00K C00G C00A 114.9(2) . . ?
C00B C00G C00A 113.7(2) . . ?
C00K C00G C00E 101.5(3) . . ?
C00B C00G C00E 110.6(2) . . ?
C00A C00G C00E 106.1(2) . . ?
C00B C00H C00I 122.5(3) . . ?
C00B C00H H00H 118.8 . . ?
C00I C00H H00H 118.8 . . ?
C009 C00I C00H 117.4(3) . . ?
C009 C00I H00I 121.3 . . ?
C00H C00I H00I 121.3 . . ?
C00M C00J C00A 121.1(3) . . ?
C00M C00J H00J 119.5 . . ?
C00A C00J H00J 119.5 . . ?
C00P C00K C00O 120.5(3) . . ?
C00P C00K C00G 131.0(3) . . ?
C00O C00K C00G 108.5(3) . . ?
C00N C00L C00F 120.5(3) . . ?
C00N C00L H00L 119.7 . . ?
C00F C00L H00L 119.7 . . ?
C00J C00M C00N 120.2(3) . . ?
C00J C00M H00M 119.9 . . ?
C00N C00M H00M 119.9 . . ?
C00L C00N C00M 119.4(3) . . ?
C00L C00N H00N 120.3 . . ?
C00M C00N H00N 120.3 . . ?
C00R C00O C00K 122.6(4) . . ?
C00R C00O N006 127.0(4) . . ?
C00K C00O N006 110.4(3) . . ?
C00K C00P C00S 118.3(4) . . ?
C00K C00P H00P 120.8 . . ?
C00S C00P H00P 120.8 . . ?
N006 C00Q H00C 109.5 . . ?
N006 C00Q H00D 109.5 . . ?
H00C C00Q H00D 109.5 . . ?
N006 C00Q H00E 109.5 . . ?
H00C C00Q H00E 109.5 . . ?
H00D C00Q H00E 109.5 . . ?
C00T C00R C00O 116.1(4) . . ?
C00T C00R H00R 121.9 . . ?
C00O C00R H00R 121.9 . . ?
C00T C00S C00P 119.5(4) . . ?
C00T C00S H00S 120.3 . . ?
C00P C00S H00S 120.3 . . ?
C00R C00T C00S 123.0(4) . . ?
C00R C00T H00T 118.5 . . ?
C00S C00T H00T 118.5 . . ?
Cl02 C00U Cl01 112.5(2) . . ?
Cl02 C00U H00G 109.1 . . ?
Cl01 C00U H00G 109.1 . . ?
Cl02 C00U H00K 109.1 . . ?
Cl01 C00U H00K 109.1 . . ?
H00G C00U H00K 107.8 . . ?

_refine_diff_density_max         1.339
_refine_diff_density_min         -1.489
_refine_diff_density_rms         0.086

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_T1_a
_database_code_depnum_ccdc_archive 'CCDC 1406284'
_audit_update_record             
;
2015-06-11 deposited with the CCDC.
2015-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H23 N3 O2'
_chemical_formula_weight         421.48

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4773(19)
_cell_length_b                   9.4856(15)
_cell_length_c                   12.418(3)
_cell_angle_alpha                82.847(9)
_cell_angle_beta                 79.354(10)
_cell_angle_gamma                76.208(9)
_cell_volume                     1061.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             458
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .15
_exptl_crystal_size_mid          .12
_exptl_crystal_size_min          .09
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29996
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_av_R_equivalents  0.1063
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4683
_reflns_number_gt                2857
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4683
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1737
_refine_ls_wR_factor_gt          0.1440
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
O001 O 0.47790(18) 0.60884(17) 0.10237(13) 0.0403(4) Uani 1 1 d . . . . .
O002 O 0.1555(2) 0.25713(16) 0.27401(14) 0.0456(5) Uani 1 1 d . . . . .
N003 N 0.3162(2) 0.78261(18) 0.20531(15) 0.0337(5) Uani 1 1 d . . . . .
N004 N -0.0333(2) 0.42994(19) 0.21339(15) 0.0335(5) Uani 1 1 d . . . . .
N005 N 0.4557(2) 0.3017(2) 0.45779(16) 0.0388(5) Uani 1 1 d . . . . .
C006 C 0.2744(2) 0.5439(2) 0.24090(17) 0.0255(5) Uani 1 1 d . . . . .
C007 C 0.3708(2) 0.6443(2) 0.17274(18) 0.0286(5) Uani 1 1 d . . . . .
C008 C 0.4781(2) 0.3024(2) 0.27322(18) 0.0287(5) Uani 1 1 d . . . . .
C009 C 0.1602(2) 0.6506(2) 0.31048(17) 0.0281(5) Uani 1 1 d . . . . .
C00A C 0.3683(2) 0.4287(2) 0.30885(17) 0.0278(5) Uani 1 1 d . . . . .
C00B C -0.0488(2) 0.5584(2) 0.14203(18) 0.0297(5) Uani 1 1 d . . . . .
C00C C 0.0888(2) 0.5908(2) 0.10635(17) 0.0275(5) Uani 1 1 d . . . . .
C00D C 0.2021(2) 0.4789(2) 0.16015(17) 0.0266(5) Uani 1 1 d . . . . .
H00D H 0.2800 0.4289 0.1028 0.032 Uiso 1 1 calc R U . . .
C00E C 0.1112(3) 0.3720(2) 0.22258(18) 0.0303(5) Uani 1 1 d . . . . .
C00F C 0.5286(2) 0.2251(2) 0.36871(19) 0.0330(5) Uani 1 1 d . . . . .
C00G C 0.1898(2) 0.7888(2) 0.28565(18) 0.0309(5) Uani 1 1 d . . . . .
C00H C 0.5384(2) 0.2460(2) 0.17148(19) 0.0336(5) Uani 1 1 d . . . . .
H00H H 0.5084 0.2962 0.1055 0.040 Uiso 1 1 calc R U . . .
C00I C 0.3603(3) 0.4224(2) 0.42061(19) 0.0337(5) Uani 1 1 d . . . . .
H00I H 0.2969 0.4925 0.4662 0.040 Uiso 1 1 calc R U . . .
C00J C 0.0397(3) 0.6317(2) 0.38721(18) 0.0342(5) Uani 1 1 d . . . . .
H00J H 0.0179 0.5380 0.4043 0.041 Uiso 1 1 calc R U . . .
C00K C 0.6424(3) 0.1160(2) 0.1688(2) 0.0398(6) Uani 1 1 d . . . . .
H00K H 0.6830 0.0768 0.1002 0.048 Uiso 1 1 calc R U . . .
C00L C 0.1000(3) 0.7099(2) 0.03290(19) 0.0388(6) Uani 1 1 d . . . . .
H00L H 0.1931 0.7335 0.0070 0.047 Uiso 1 1 calc R U . . .
C00M C 0.6336(3) 0.0945(2) 0.3656(2) 0.0425(6) Uani 1 1 d . . . . .
H00M H 0.6659 0.0441 0.4307 0.051 Uiso 1 1 calc R U . . .
C00N C 0.1022(3) 0.9093(2) 0.3354(2) 0.0434(6) Uani 1 1 d . . . . .
H00N H 0.1230 1.0034 0.3174 0.052 Uiso 1 1 calc R U . . .
C00O C -0.0500(3) 0.7505(3) 0.4397(2) 0.0426(6) Uani 1 1 d . . . . .
H00O H -0.1325 0.7379 0.4934 0.051 Uiso 1 1 calc R U . . .
C00P C 0.6891(3) 0.0412(2) 0.2643(2) 0.0452(7) Uani 1 1 d . . . . .
H00P H 0.7603 -0.0482 0.2595 0.054 Uiso 1 1 calc R U . . .
C00Q C -0.1748(3) 0.6406(3) 0.1069(2) 0.0419(6) Uani 1 1 d . . . . .
H00Q H -0.2676 0.6161 0.1321 0.050 Uiso 1 1 calc R U . . .
C00R C -0.0187(3) 0.8859(3) 0.4136(2) 0.0467(7) Uani 1 1 d . . . . .
H00R H -0.0809 0.9662 0.4498 0.056 Uiso 1 1 calc R U . . .
C00S C -0.1613(3) 0.7605(3) 0.0333(2) 0.0481(7) Uani 1 1 d . . . . .
H00S H -0.2463 0.8196 0.0074 0.058 Uiso 1 1 calc R U . . .
C00T C -0.0262(3) 0.7959(3) -0.0034(2) 0.0479(7) Uani 1 1 d . . . . .
H00T H -0.0193 0.8792 -0.0535 0.058 Uiso 1 1 calc R U . . .
C00U C -0.1529(3) 0.3612(3) 0.2654(2) 0.0516(7) Uani 1 1 d . . . . .
H00A H -0.1975 0.3324 0.2088 0.077 Uiso 1 1 calc R U . . .
H00B H -0.2274 0.4300 0.3103 0.077 Uiso 1 1 calc R U . . .
H00C H -0.1147 0.2748 0.3123 0.077 Uiso 1 1 calc R U . . .
C00V C 0.3816(3) 0.9062(3) 0.1616(2) 0.0518(7) Uani 1 1 d . . . . .
H00E H 0.3984 0.9535 0.2225 0.078 Uiso 1 1 calc R U . . .
H00F H 0.3147 0.9762 0.1188 0.078 Uiso 1 1 calc R U . . .
H00G H 0.4755 0.8724 0.1142 0.078 Uiso 1 1 calc R U . . .
C00W C 0.4775(3) 0.2631(3) 0.5717(2) 0.0536(7) Uani 1 1 d . . . . .
H00U H 0.4609 0.1649 0.5948 0.080 Uiso 1 1 calc R U . . .
H00V H 0.4079 0.3330 0.6186 0.080 Uiso 1 1 calc R U . . .
H00W H 0.5784 0.2653 0.5782 0.080 Uiso 1 1 calc R U . . .


_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
O001 C007 1.221(3) . ?
O002 C00E 1.216(3) . ?
N003 C007 1.372(3) . ?
N003 C00G 1.405(3) . ?
N003 C00V 1.455(3) . ?
N004 C00E 1.369(3) . ?
N004 C00B 1.409(3) . ?
N004 C00U 1.450(3) . ?
N005 C00I 1.368(3) . ?
N005 C00F 1.381(3) . ?
N005 C00W 1.456(3) . ?
C006 C00A 1.510(3) . ?
C006 C009 1.514(3) . ?
C006 C007 1.545(3) . ?
C006 C00D 1.570(3) . ?
C008 C00H 1.402(3) . ?
C008 C00F 1.414(3) . ?
C008 C00A 1.443(3) . ?
C009 C00J 1.377(3) . ?
C009 C00G 1.392(3) . ?
C00A C00I 1.370(3) . ?
C00B C00Q 1.374(3) . ?
C00B C00C 1.391(3) . ?
C00C C00L 1.373(3) . ?
C00C C00D 1.507(3) . ?
C00D C00E 1.532(3) . ?
C00D H00D 1.0000 . ?
C00F C00M 1.391(3) . ?
C00G C00N 1.382(3) . ?
C00H C00K 1.382(3) . ?
C00H H00H 0.9500 . ?
C00I H00I 0.9500 . ?
C00J C00O 1.393(3) . ?
C00J H00J 0.9500 . ?
C00K C00P 1.393(4) . ?
C00K H00K 0.9500 . ?
C00L C00T 1.394(3) . ?
C00L H00L 0.9500 . ?
C00M C00P 1.379(4) . ?
C00M H00M 0.9500 . ?
C00N C00R 1.401(4) . ?
C00N H00N 0.9500 . ?
C00O C00R 1.373(3) . ?
C00O H00O 0.9500 . ?
C00P H00P 0.9500 . ?
C00Q C00S 1.383(3) . ?
C00Q H00Q 0.9500 . ?
C00R H00R 0.9500 . ?
C00S C00T 1.382(4) . ?
C00S H00S 0.9500 . ?
C00T H00T 0.9500 . ?
C00U H00A 0.9800 . ?
C00U H00B 0.9800 . ?
C00U H00C 0.9800 . ?
C00V H00E 0.9800 . ?
C00V H00F 0.9800 . ?
C00V H00G 0.9800 . ?
C00W H00U 0.9800 . ?
C00W H00V 0.9800 . ?
C00W H00W 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C007 N003 C00G 111.29(16) . . ?
C007 N003 C00V 124.0(2) . . ?
C00G N003 C00V 124.73(19) . . ?
C00E N004 C00B 111.40(17) . . ?
C00E N004 C00U 123.59(19) . . ?
C00B N004 C00U 124.9(2) . . ?
C00I N005 C00F 108.22(18) . . ?
C00I N005 C00W 125.4(2) . . ?
C00F N005 C00W 126.3(2) . . ?
C00A C006 C009 112.65(17) . . ?
C00A C006 C007 109.01(17) . . ?
C009 C006 C007 101.62(16) . . ?
C00A C006 C00D 113.20(16) . . ?
C009 C006 C00D 111.11(17) . . ?
C007 C006 C00D 108.52(16) . . ?
O001 C007 N003 125.03(19) . . ?
O001 C007 C006 126.78(19) . . ?
N003 C007 C006 108.19(18) . . ?
C00H C008 C00F 118.4(2) . . ?
C00H C008 C00A 134.9(2) . . ?
C00F C008 C00A 106.7(2) . . ?
C00J C009 C00G 119.4(2) . . ?
C00J C009 C006 131.33(18) . . ?
C00G C009 C006 109.25(18) . . ?
C00I C00A C008 105.99(19) . . ?
C00I C00A C006 125.4(2) . . ?
C008 C00A C006 128.62(19) . . ?
C00Q C00B C00C 122.8(2) . . ?
C00Q C00B N004 128.0(2) . . ?
C00C C00B N004 109.10(19) . . ?
C00L C00C C00B 118.9(2) . . ?
C00L C00C C00D 132.0(2) . . ?
C00B C00C C00D 109.05(18) . . ?
C00C C00D C00E 102.20(17) . . ?
C00C C00D C006 113.37(16) . . ?
C00E C00D C006 110.94(17) . . ?
C00C C00D H00D 110.0 . . ?
C00E C00D H00D 110.0 . . ?
C006 C00D H00D 110.0 . . ?
O002 C00E N004 124.7(2) . . ?
O002 C00E C00D 127.5(2) . . ?
N004 C00E C00D 107.83(17) . . ?
N005 C00F C00M 129.4(2) . . ?
N005 C00F C008 108.06(19) . . ?
C00M C00F C008 122.5(2) . . ?
C00N C00G C009 122.3(2) . . ?
C00N C00G N003 128.06(19) . . ?
C009 C00G N003 109.62(18) . . ?
C00K C00H C008 118.8(2) . . ?
C00K C00H H00H 120.6 . . ?
C008 C00H H00H 120.6 . . ?
N005 C00I C00A 111.0(2) . . ?
N005 C00I H00I 124.5 . . ?
C00A C00I H00I 124.5 . . ?
C009 C00J C00O 119.7(2) . . ?
C009 C00J H00J 120.1 . . ?
C00O C00J H00J 120.1 . . ?
C00H C00K C00P 121.6(2) . . ?
C00H C00K H00K 119.2 . . ?
C00P C00K H00K 119.2 . . ?
C00C C00L C00T 119.4(2) . . ?
C00C C00L H00L 120.3 . . ?
C00T C00L H00L 120.3 . . ?
C00P C00M C00F 117.5(2) . . ?
C00P C00M H00M 121.3 . . ?
C00F C00M H00M 121.3 . . ?
C00G C00N C00R 116.7(2) . . ?
C00G C00N H00N 121.6 . . ?
C00R C00N H00N 121.6 . . ?
C00R C00O C00J 119.8(2) . . ?
C00R C00O H00O 120.1 . . ?
C00J C00O H00O 120.1 . . ?
C00M C00P C00K 121.1(2) . . ?
C00M C00P H00P 119.4 . . ?
C00K C00P H00P 119.4 . . ?
C00B C00Q C00S 117.4(2) . . ?
C00B C00Q H00Q 121.3 . . ?
C00S C00Q H00Q 121.3 . . ?
C00O C00R C00N 122.0(2) . . ?
C00O C00R H00R 119.0 . . ?
C00N C00R H00R 119.0 . . ?
C00T C00S C00Q 121.2(2) . . ?
C00T C00S H00S 119.4 . . ?
C00Q C00S H00S 119.4 . . ?
C00S C00T C00L 120.2(2) . . ?
C00S C00T H00T 119.9 . . ?
C00L C00T H00T 119.9 . . ?
N004 C00U H00A 109.5 . . ?
N004 C00U H00B 109.5 . . ?
H00A C00U H00B 109.5 . . ?
N004 C00U H00C 109.5 . . ?
H00A C00U H00C 109.5 . . ?
H00B C00U H00C 109.5 . . ?
N003 C00V H00E 109.5 . . ?
N003 C00V H00F 109.5 . . ?
H00E C00V H00F 109.5 . . ?
N003 C00V H00G 109.5 . . ?
H00E C00V H00G 109.5 . . ?
H00F C00V H00G 109.5 . . ?
N005 C00W H00U 109.5 . . ?
N005 C00W H00V 109.5 . . ?
H00U C00W H00V 109.5 . . ?
N005 C00W H00W 109.5 . . ?
H00U C00W H00W 109.5 . . ?
H00V C00W H00W 109.5 . . ?

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.044

_shelxl_version_number           2014/6

