# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2014

####################################################################### 
# 
# 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_140702_188_9
_audit_block_doi                 10.5517/cc12yz22
_database_code_depnum_ccdc_archive 'CCDC 1011904'
_audit_update_record             
;
2014-10-23 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_date             2014-07-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H20 N2 O2'
_chemical_formula_sum            'C20 H20 N2 O2'
_chemical_formula_weight         320.38
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   10.2550(10)
_cell_length_b                   10.8108(12)
_cell_length_c                   15.4763(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1715.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2289
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5446
_cell_measurement_theta_min      3.0318
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10865
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.04
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0335274000
_diffrn_orient_matrix_UB_12      0.0076708000
_diffrn_orient_matrix_UB_13      0.0397499000
_diffrn_orient_matrix_UB_21      0.0130725000
_diffrn_orient_matrix_UB_22      0.0643648000
_diffrn_orient_matrix_UB_23      -0.0011698000
_diffrn_orient_matrix_UB_31      -0.0590849000
_diffrn_orient_matrix_UB_32      0.0099357000
_diffrn_orient_matrix_UB_33      -0.0228105000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1299
_reflns_number_total             1803
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         1803
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0500
_refine_ls_restrained_S_all      1.049
_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)+(0.0559P)²+0.3081P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1290
_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:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C4(H4), C12(H12), C13(H13), C16(H16),
 C17(H17), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C20(H20A,H20B,H20C)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.8666(3) 0.4167(3) 0.75964(16) 0.0653(7) Uani 1 d . . .
O2 O 0.9636(3) 0.2108(3) 0.60784(19) 0.0698(8) Uani 1 d . . .
N1 N 0.8787(3) 0.6223(3) 0.48261(19) 0.0509(8) Uani 1 d . . .
N2 N 0.8726(3) 0.4901(3) 0.62227(19) 0.0509(7) Uani 1 d . . .
H2 H 0.8457 0.4747 0.5707 0.061 Uiso 1 calc . . R
C1 C 0.8836(4) 0.6766(4) 0.4046(2) 0.0563(10) Uani 1 d . . .
H1 H 0.8294 0.6470 0.3611 0.068 Uiso 1 calc . . R
C2 C 0.9650(5) 0.7734(4) 0.3863(3) 0.0694(12) Uani 1 d . . .
H2A H 0.9669 0.8085 0.3314 0.083 Uiso 1 calc . . R
C3 C 1.0435(5) 0.8171(4) 0.4508(3) 0.0740(12) Uani 1 d . . .
H3 H 1.1003 0.8824 0.4400 0.089 Uiso 1 calc . . R
C4 C 1.0385(4) 0.7651(4) 0.5307(3) 0.0645(11) Uani 1 d . . .
H4 H 1.0898 0.7961 0.5753 0.077 Uiso 1 calc . . R
C5 C 0.9563(3) 0.6654(3) 0.5452(2) 0.0457(9) Uani 1 d . . .
C6 C 0.9478(4) 0.6036(3) 0.6335(2) 0.0480(9) Uani 1 d . . .
C7 C 0.8770(4) 0.6910(4) 0.6949(3) 0.0642(11) Uani 1 d . . .
H7A H 0.8693 0.6528 0.7507 0.096 Uiso 1 calc . . GR
H7B H 0.7916 0.7087 0.6726 0.096 Uiso 1 calc . . GR
H7C H 0.9255 0.7666 0.7001 0.096 Uiso 1 calc . . GR
C8 C 1.0840(4) 0.5720(4) 0.6674(3) 0.0669(12) Uani 1 d . . .
H8A H 1.1298 0.5237 0.6251 0.100 Uiso 1 calc . . GR
H8B H 1.0764 0.5256 0.7200 0.100 Uiso 1 calc . . GR
H8C H 1.1313 0.6471 0.6784 0.100 Uiso 1 calc . . GR
C9 C 0.8406(3) 0.4073(4) 0.6828(2) 0.0509(9) Uani 1 d . . .
C10 C 0.7659(4) 0.2978(3) 0.6482(2) 0.0499(9) Uani 1 d . . .
C11 C 0.8322(4) 0.1994(4) 0.6128(2) 0.0545(10) Uani 1 d . . .
C12 C 0.7627(4) 0.0944(4) 0.5842(3) 0.0705(12) Uani 1 d . . .
H12 H 0.8073 0.0267 0.5618 0.085 Uiso 1 calc . . R
C13 C 0.6323(5) 0.0927(4) 0.5896(3) 0.0758(12) Uani 1 d . . .
H13 H 0.5886 0.0222 0.5709 0.091 Uiso 1 calc . . R
C14 C 0.5580(4) 0.1913(4) 0.6219(3) 0.0644(11) Uani 1 d . . .
C15 C 0.6278(4) 0.2970(4) 0.6536(2) 0.0536(9) Uani 1 d . . .
C16 C 0.5558(4) 0.3976(4) 0.6863(2) 0.0593(10) Uani 1 d . . .
H16 H 0.6000 0.4662 0.7077 0.071 Uiso 1 calc . . R
C17 C 0.4227(4) 0.3969(5) 0.6874(3) 0.0730(12) Uani 1 d . . .
H17 H 0.3772 0.4643 0.7095 0.088 Uiso 1 calc . . R
C18 C 0.3549(5) 0.2945(5) 0.6551(3) 0.0788(14) Uani 1 d . . .
H18 H 0.2642 0.2946 0.6542 0.095 Uiso 1 calc . . R
C19 C 0.4219(5) 0.1948(5) 0.6249(3) 0.0802(14) Uani 1 d . . .
H19 H 0.3753 0.1263 0.6056 0.096 Uiso 1 calc . . R
C20 C 1.0363(5) 0.1135(5) 0.5674(3) 0.0802(14) Uani 1 d . . .
H20A H 1.0244 0.0381 0.5992 0.120 Uiso 1 calc . . GR
H20B H 1.1272 0.1349 0.5667 0.120 Uiso 1 calc . . GR
H20C H 1.0061 0.1024 0.5092 0.120 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.223(4) . ?
O2 C11 1.355(5) . ?
O2 C20 1.433(5) . ?
N1 C1 1.344(5) . ?
N1 C5 1.337(4) . ?
N2 H2 0.8600 . ?
N2 C6 1.459(4) . ?
N2 C9 1.336(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.368(6) . ?
C2 H2A 0.9300 . ?
C2 C3 1.367(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.360(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(5) . ?
C5 C6 1.524(5) . ?
C6 C7 1.525(5) . ?
C6 C8 1.531(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.508(5) . ?
C10 C11 1.376(5) . ?
C10 C15 1.418(5) . ?
C11 C12 1.412(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.341(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.403(6) . ?
C14 C15 1.435(5) . ?
C14 C19 1.397(6) . ?
C15 C16 1.409(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.365(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.400(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.361(7) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C11 O2 C20 118.4(3) . . ?
C5 N1 C1 118.4(3) . . ?
C6 N2 H2 116.2 . . ?
C9 N2 H2 116.2 . . ?
C9 N2 C6 127.6(3) . . ?
N1 C1 H1 118.6 . . ?
N1 C1 C2 122.9(4) . . ?
C2 C1 H1 118.6 . . ?
C1 C2 H2A 120.9 . . ?
C3 C2 C1 118.2(4) . . ?
C3 C2 H2A 120.9 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 121.1(4) . . ?
N1 C5 C6 117.5(3) . . ?
C4 C5 C6 121.4(3) . . ?
N2 C6 C5 107.0(3) . . ?
N2 C6 C7 110.1(3) . . ?
N2 C6 C8 109.6(3) . . ?
C5 C6 C7 108.3(3) . . ?
C5 C6 C8 110.7(3) . . ?
C7 C6 C8 111.0(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 N2 124.9(4) . . ?
O1 C9 C10 121.4(3) . . ?
N2 C9 C10 113.7(3) . . ?
C11 C10 C9 119.8(3) . . ?
C11 C10 C15 120.8(3) . . ?
C15 C10 C9 119.4(3) . . ?
O2 C11 C10 116.3(3) . . ?
O2 C11 C12 123.8(4) . . ?
C10 C11 C12 119.8(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.6(4) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 118.2 . . ?
C12 C13 C14 123.6(4) . . ?
C14 C13 H13 118.2 . . ?
C13 C14 C15 117.2(4) . . ?
C19 C14 C13 125.1(4) . . ?
C19 C14 C15 117.8(4) . . ?
C10 C15 C14 118.9(4) . . ?
C16 C15 C10 122.7(4) . . ?
C16 C15 C14 118.4(4) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.6(4) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.8(5) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.9(4) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 H19 118.8 . . ?
C18 C19 C14 122.4(5) . . ?
C18 C19 H19 118.8 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C9 C10 C11 -96.5(5) . . . . ?
O1 C9 C10 C15 82.7(4) . . . . ?
O2 C11 C12 C13 -178.2(4) . . . . ?
N1 C1 C2 C3 -0.7(6) . . . . ?
N1 C5 C6 N2 12.2(4) . . . . ?
N1 C5 C6 C7 -106.5(4) . . . . ?
N1 C5 C6 C8 131.6(4) . . . . ?
N2 C9 C10 C11 84.1(4) . . . . ?
N2 C9 C10 C15 -96.7(4) . . . . ?
C1 N1 C5 C4 1.1(5) . . . . ?
C1 N1 C5 C6 179.2(3) . . . . ?
C1 C2 C3 C4 -0.5(7) . . . . ?
C2 C3 C4 C5 1.9(7) . . . . ?
C3 C4 C5 N1 -2.3(6) . . . . ?
C3 C4 C5 C6 179.7(4) . . . . ?
C4 C5 C6 N2 -169.7(3) . . . . ?
C4 C5 C6 C7 71.6(4) . . . . ?
C4 C5 C6 C8 -50.3(5) . . . . ?
C5 N1 C1 C2 0.3(5) . . . . ?
C6 N2 C9 O1 2.7(6) . . . . ?
C6 N2 C9 C10 -177.9(3) . . . . ?
C9 N2 C6 C5 -179.6(3) . . . . ?
C9 N2 C6 C7 -62.1(5) . . . . ?
C9 N2 C6 C8 60.3(5) . . . . ?
C9 C10 C11 O2 -3.0(5) . . . . ?
C9 C10 C11 C12 177.0(4) . . . . ?
C9 C10 C15 C14 -178.9(3) . . . . ?
C9 C10 C15 C16 3.3(5) . . . . ?
C10 C11 C12 C13 1.8(7) . . . . ?
C10 C15 C16 C17 177.1(4) . . . . ?
C11 C10 C15 C14 0.3(5) . . . . ?
C11 C10 C15 C16 -177.6(3) . . . . ?
C11 C12 C13 C14 0.6(7) . . . . ?
C12 C13 C14 C15 -2.4(7) . . . . ?
C12 C13 C14 C19 177.0(5) . . . . ?
C13 C14 C15 C10 1.9(5) . . . . ?
C13 C14 C15 C16 179.9(4) . . . . ?
C13 C14 C19 C18 -178.3(5) . . . . ?
C14 C15 C16 C17 -0.8(6) . . . . ?
C15 C10 C11 O2 177.8(3) . . . . ?
C15 C10 C11 C12 -2.2(6) . . . . ?
C15 C14 C19 C18 1.2(7) . . . . ?
C15 C16 C17 C18 -0.3(6) . . . . ?
C16 C17 C18 C19 1.8(7) . . . . ?
C17 C18 C19 C14 -2.3(8) . . . . ?
C19 C14 C15 C10 -177.6(4) . . . . ?
C19 C14 C15 C16 0.4(6) . . . . ?
C20 O2 C11 C10 -176.8(4) . . . . ?
C20 O2 C11 C12 3.2(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_140701_195_37
_audit_block_doi                 10.5517/cc12yz33
_database_code_depnum_ccdc_archive 'CCDC 1011905'
_audit_update_record             
;
2014-10-23 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_date             2014-07-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H17 F3 N2 O2'
_chemical_formula_sum            'C17 H17 F3 N2 O2'
_chemical_formula_weight         338.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.5428(12)
_cell_length_b                   16.2625(12)
_cell_length_c                   10.8624(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.846(16)
_cell_angle_gamma                90.00
_cell_volume                     1631.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2098
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5617
_cell_measurement_theta_min      3.3316
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.38
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10009
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.34
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0521682000
_diffrn_orient_matrix_UB_12      -0.0298822000
_diffrn_orient_matrix_UB_13      -0.0416492000
_diffrn_orient_matrix_UB_21      -0.0346246000
_diffrn_orient_matrix_UB_22      0.0293410000
_diffrn_orient_matrix_UB_23      -0.0544946000
_diffrn_orient_matrix_UB_31      0.0444714000
_diffrn_orient_matrix_UB_32      -0.0121721000
_diffrn_orient_matrix_UB_33      -0.0292136000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1960
_reflns_number_total             2981
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2981
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.065
_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)+(0.0592P)²+0.5724P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1572
_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:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C4(H4), C11(H11), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C17(H17A,H17B,H17C)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F 0.6041(2) 0.73878(18) 0.9728(3) 0.1335(10) Uani 1 d . . .
F2 F 0.6659(2) 0.67795(17) 1.1593(3) 0.1430(11) Uani 1 d . . .
F3 F 0.6515(2) 0.80656(15) 1.1524(3) 0.1574(13) Uani 1 d . . .
O1 O 0.1786(2) 0.56299(11) 0.7597(2) 0.0648(6) Uani 1 d . . .
O2 O 0.00520(19) 0.70849(10) 0.9541(2) 0.0625(5) Uani 1 d . . .
N1 N -0.2242(2) 0.54293(13) 0.8517(2) 0.0587(6) Uani 1 d . . .
N2 N -0.0014(2) 0.56919(11) 0.8167(2) 0.0493(5) Uani 1 d . . .
H2 H -0.0313 0.5951 0.8669 0.059 Uiso 1 calc . . R
C1 C -0.3385(3) 0.53846(18) 0.8738(3) 0.0721(8) Uani 1 d . . .
H1 H -0.3387 0.5718 0.9433 0.087 Uiso 1 calc . . R
C2 C -0.4542(3) 0.4881(2) 0.8010(4) 0.0776(9) Uani 1 d . . .
H2A H -0.5333 0.4884 0.8170 0.093 Uiso 1 calc . . R
C3 C -0.4494(4) 0.4375(2) 0.7041(4) 0.0906(11) Uani 1 d . . .
H3 H -0.5248 0.4009 0.6541 0.109 Uiso 1 calc . . R
C4 C -0.3333(4) 0.4403(2) 0.6799(3) 0.0824(10) Uani 1 d . . .
H4 H -0.3295 0.4056 0.6137 0.099 Uiso 1 calc . . R
C5 C -0.2216(3) 0.49509(15) 0.7548(3) 0.0530(6) Uani 1 d . . .
C6 C -0.0927(3) 0.50181(14) 0.7282(3) 0.0505(6) Uani 1 d . . .
C7 C -0.1461(3) 0.52248(18) 0.5726(3) 0.0673(8) Uani 1 d . . .
H7A H -0.1990 0.5733 0.5495 0.101 Uiso 1 calc . . GR
H7B H -0.2080 0.4792 0.5146 0.101 Uiso 1 calc . . GR
H7C H -0.0644 0.5279 0.5567 0.101 Uiso 1 calc . . GR
C8 C -0.0079(3) 0.42094(15) 0.7686(3) 0.0676(8) Uani 1 d . . .
H8A H 0.0738 0.4255 0.7527 0.101 Uiso 1 calc . . GR
H8B H -0.0696 0.3771 0.7123 0.101 Uiso 1 calc . . GR
H8C H 0.0251 0.4095 0.8661 0.101 Uiso 1 calc . . GR
C9 C 0.1235(3) 0.59379(14) 0.8264(3) 0.0471(6) Uani 1 d . . .
C10 C 0.2033(3) 0.66349(13) 0.9275(2) 0.0444(6) Uani 1 d . . .
C11 C 0.3466(3) 0.67344(14) 0.9608(3) 0.0504(6) Uani 1 d . . .
H11 H 0.3859 0.6382 0.9205 0.060 Uiso 1 calc . . R
C12 C 0.4334(3) 0.73398(15) 1.0519(3) 0.0527(6) Uani 1 d . . .
C13 C 0.3746(3) 0.78656(15) 1.1108(3) 0.0575(7) Uani 1 d . . .
H13 H 0.4321 0.8274 1.1724 0.069 Uiso 1 calc . . R
C14 C 0.2328(3) 0.77937(15) 1.0797(3) 0.0546(7) Uani 1 d . . .
H14 H 0.1945 0.8155 1.1194 0.065 Uiso 1 calc . . R
C15 C 0.1462(3) 0.71811(13) 0.9887(3) 0.0456(6) Uani 1 d . . .
C16 C 0.5866(3) 0.7405(2) 1.0872(4) 0.0761(9) Uani 1 d . . .
C17 C -0.0593(3) 0.76447(18) 1.0086(4) 0.0746(9) Uani 1 d . . .
H17A H -0.1593 0.7504 0.9731 0.112 Uiso 1 calc . . GR
H17B H -0.0522 0.8194 0.9800 0.112 Uiso 1 calc . . GR
H17C H -0.0097 0.7613 1.1093 0.112 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C16 1.341(4) . ?
F2 C16 1.309(4) . ?
F3 C16 1.288(3) . ?
O1 C9 1.232(3) . ?
O2 C15 1.355(3) . ?
O2 C17 1.424(3) . ?
N1 C1 1.339(3) . ?
N1 C5 1.319(3) . ?
N2 H2 0.8600 . ?
N2 C6 1.470(3) . ?
N2 C9 1.331(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.362(4) . ?
C2 H2A 0.9300 . ?
C2 C3 1.356(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(4) . ?
C5 C6 1.524(4) . ?
C6 C7 1.539(4) . ?
C6 C8 1.531(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.519(3) . ?
C10 C11 1.383(3) . ?
C10 C15 1.408(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(3) . ?
C12 C13 1.381(3) . ?
C12 C16 1.472(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.369(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.390(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C15 O2 C17 119.4(2) . . ?
C5 N1 C1 118.6(2) . . ?
C6 N2 H2 117.1 . . ?
C9 N2 H2 117.1 . . ?
C9 N2 C6 125.9(2) . . ?
N1 C1 H1 118.0 . . ?
N1 C1 C2 124.0(3) . . ?
C2 C1 H1 118.0 . . ?
C1 C2 H2A 121.4 . . ?
C3 C2 C1 117.2(3) . . ?
C3 C2 H2A 121.4 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 120.6(3) . . ?
N1 C5 C6 118.2(2) . . ?
C4 C5 C6 121.2(2) . . ?
N2 C6 C5 106.96(19) . . ?
N2 C6 C7 109.5(2) . . ?
N2 C6 C8 110.2(2) . . ?
C5 C6 C7 109.7(2) . . ?
C5 C6 C8 109.6(2) . . ?
C8 C6 C7 110.9(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 N2 124.1(2) . . ?
O1 C9 C10 118.4(2) . . ?
N2 C9 C10 117.6(2) . . ?
C11 C10 C9 115.5(2) . . ?
C11 C10 C15 117.7(2) . . ?
C15 C10 C9 126.8(2) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 C10 122.2(2) . . ?
C12 C11 H11 118.9 . . ?
C11 C12 C16 120.1(2) . . ?
C13 C12 C11 118.9(2) . . ?
C13 C12 C16 121.0(2) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.9(2) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.1(2) . . ?
C15 C14 H14 119.9 . . ?
O2 C15 C10 117.3(2) . . ?
O2 C15 C14 122.5(2) . . ?
C14 C15 C10 120.3(2) . . ?
F1 C16 C12 112.4(3) . . ?
F2 C16 F1 101.8(3) . . ?
F2 C16 C12 113.8(3) . . ?
F3 C16 F1 104.6(3) . . ?
F3 C16 F2 107.6(3) . . ?
F3 C16 C12 115.4(3) . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C9 C10 C11 -14.8(3) . . . . ?
O1 C9 C10 C15 164.9(2) . . . . ?
N1 C1 C2 C3 2.6(5) . . . . ?
N1 C5 C6 N2 -4.2(3) . . . . ?
N1 C5 C6 C7 -122.9(2) . . . . ?
N1 C5 C6 C8 115.2(3) . . . . ?
N2 C9 C10 C11 164.5(2) . . . . ?
N2 C9 C10 C15 -15.8(4) . . . . ?
C1 N1 C5 C4 -1.3(4) . . . . ?
C1 N1 C5 C6 178.8(2) . . . . ?
C1 C2 C3 C4 -2.0(5) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C3 C4 C5 N1 1.8(5) . . . . ?
C3 C4 C5 C6 -178.3(3) . . . . ?
C4 C5 C6 N2 175.9(2) . . . . ?
C4 C5 C6 C7 57.2(3) . . . . ?
C4 C5 C6 C8 -64.7(3) . . . . ?
C5 N1 C1 C2 -0.9(4) . . . . ?
C6 N2 C9 O1 0.8(4) . . . . ?
C6 N2 C9 C10 -178.4(2) . . . . ?
C9 N2 C6 C5 178.5(2) . . . . ?
C9 N2 C6 C7 -62.6(3) . . . . ?
C9 N2 C6 C8 59.5(3) . . . . ?
C9 C10 C11 C12 -179.7(2) . . . . ?
C9 C10 C15 O2 -0.5(4) . . . . ?
C9 C10 C15 C14 -179.8(2) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C10 C11 C12 C16 178.2(3) . . . . ?
C11 C10 C15 O2 179.2(2) . . . . ?
C11 C10 C15 C14 -0.2(3) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C11 C12 C16 F1 48.6(4) . . . . ?
C11 C12 C16 F2 -66.5(4) . . . . ?
C11 C12 C16 F3 168.4(3) . . . . ?
C12 C13 C14 C15 0.6(4) . . . . ?
C13 C12 C16 F1 -132.8(3) . . . . ?
C13 C12 C16 F2 112.1(3) . . . . ?
C13 C12 C16 F3 -13.0(5) . . . . ?
C13 C14 C15 O2 -179.8(2) . . . . ?
C13 C14 C15 C10 -0.4(4) . . . . ?
C15 C10 C11 C12 0.6(4) . . . . ?
C16 C12 C13 C14 -178.8(3) . . . . ?
C17 O2 C15 C10 -177.3(2) . . . . ?
C17 O2 C15 C14 2.1(4) . . . . ?

####################################################################### 
# 
# 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_140702_192_22
_audit_block_doi                 10.5517/cc12zrjb
_database_code_depnum_ccdc_archive 'CCDC 1012662'
_audit_update_record             
;
2014-10-23 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_date             2014-07-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H19 N3 O2'
_chemical_formula_sum            'C16 H19 N3 O2'
_chemical_formula_weight         285.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8'
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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.0742(5)
_cell_length_b                   12.4409(10)
_cell_length_c                   17.6473(12)
_cell_angle_alpha                71.940(7)
_cell_angle_beta                 79.009(6)
_cell_angle_gamma                72.177(6)
_cell_volume                     1595.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2395
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5639
_cell_measurement_theta_min      3.3293
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.4
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10519
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.34
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0251750000
_diffrn_orient_matrix_UB_12      -0.0349189000
_diffrn_orient_matrix_UB_13      -0.0184535000
_diffrn_orient_matrix_UB_21      -0.0049573000
_diffrn_orient_matrix_UB_22      -0.0422764000
_diffrn_orient_matrix_UB_23      0.0374968000
_diffrn_orient_matrix_UB_31      -0.0891793000
_diffrn_orient_matrix_UB_32      0.0293306000
_diffrn_orient_matrix_UB_33      0.0078062000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3700
_reflns_number_total             5817
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         5817
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0881P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1451
_refine_ls_wR_factor_ref         0.1689
_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:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N5(H5), C18(H18), C21(H21), C29(H29), C30(H30), C31(H31), C32(H32), N2(H2),
 C2(H2A), C5(H5A), C13(H13), C14(H14), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C10(H10A,H10B,H10C), C11(H11A,H11B,
 H11C)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O3 O 0.31256(18) 0.27148(12) 0.54334(10) 0.0590(4) Uani 1 d . . .
O4 O 0.84135(19) 0.13991(13) 0.56868(11) 0.0624(5) Uani 1 d . . .
N4 N 0.6730(3) 0.44260(16) 0.39646(11) 0.0580(5) Uani 1 d . . .
N5 N 0.5931(2) 0.08297(13) 0.58298(10) 0.0456(4) Uani 1 d . . .
H5 H 0.4858 0.1065 0.5729 0.055 Uiso 1 calc . . R
N6 N 0.3499(2) -0.02557(15) 0.62508(10) 0.0473(4) Uani 1 d . . .
C17 C 0.4996(3) 0.49180(18) 0.39170(13) 0.0558(6) Uani 1 d . . .
C18 C 0.3763(3) 0.43816(18) 0.43984(13) 0.0530(6) Uani 1 d . . .
H18 H 0.2581 0.4748 0.4355 0.064 Uiso 1 calc . . R
C19 C 0.4266(3) 0.32994(17) 0.49483(13) 0.0467(5) Uani 1 d . . .
C20 C 0.6051(3) 0.27738(16) 0.50101(12) 0.0438(5) Uani 1 d . . .
C21 C 0.7184(3) 0.33925(18) 0.45023(13) 0.0516(6) Uani 1 d . . .
H21 H 0.8374 0.3054 0.4541 0.062 Uiso 1 calc . . R
C22 C 0.4478(4) 0.6066(2) 0.33070(16) 0.0781(8) Uani 1 d . . .
H22A H 0.4266 0.5936 0.2829 0.117 Uiso 1 calc . . GR
H22B H 0.5402 0.6448 0.3183 0.117 Uiso 1 calc . . GR
H22C H 0.3433 0.6552 0.3516 0.117 Uiso 1 calc . . GR
C23 C 0.1298(3) 0.3240(2) 0.53969(18) 0.0741(8) Uani 1 d . . .
H23A H 0.0659 0.2700 0.5737 0.111 Uiso 1 calc . . GR
H23B H 0.1033 0.3434 0.4855 0.111 Uiso 1 calc . . GR
H23C H 0.0968 0.3940 0.5574 0.111 Uiso 1 calc . . GR
C24 C 0.6884(3) 0.16043(17) 0.55523(13) 0.0459(5) Uani 1 d . . .
C25 C 0.6567(3) -0.03940(16) 0.62945(12) 0.0431(5) Uani 1 d . . .
C26 C 0.8055(3) -0.10519(18) 0.57930(14) 0.0536(6) Uani 1 d . . .
H26A H 0.8997 -0.0683 0.5651 0.080 Uiso 1 calc . . GR
H26B H 0.7637 -0.1036 0.5315 0.080 Uiso 1 calc . . GR
H26C H 0.8466 -0.1850 0.6099 0.080 Uiso 1 calc . . GR
C27 C 0.7138(3) -0.0444(2) 0.70895(13) 0.0571(6) Uani 1 d . . .
H27A H 0.6164 -0.0046 0.7395 0.086 Uiso 1 calc . . GR
H27B H 0.8070 -0.0072 0.6982 0.086 Uiso 1 calc . . GR
H27C H 0.7537 -0.1248 0.7388 0.086 Uiso 1 calc . . GR
C28 C 0.5040(3) -0.09469(17) 0.64790(12) 0.0436(5) Uani 1 d . . .
C29 C 0.5256(3) -0.21253(18) 0.68791(14) 0.0557(6) Uani 1 d . . .
H29 H 0.6347 -0.2598 0.7026 0.067 Uiso 1 calc . . R
C30 C 0.3838(4) -0.2585(2) 0.70549(14) 0.0617(7) Uani 1 d . . .
H30 H 0.3956 -0.3371 0.7329 0.074 Uiso 1 calc . . R
C31 C 0.2241(3) -0.1872(2) 0.68207(14) 0.0608(6) Uani 1 d . . .
H31 H 0.1263 -0.2163 0.6934 0.073 Uiso 1 calc . . R
C32 C 0.2132(3) -0.0722(2) 0.64156(14) 0.0569(6) Uani 1 d . . .
H32 H 0.1061 -0.0242 0.6247 0.068 Uiso 1 calc . . R
O1 O 0.9537(2) 0.75262(13) -0.03090(9) 0.0661(5) Uani 1 d . . .
O2 O 1.1427(2) 0.59964(13) 0.19183(10) 0.0708(5) Uani 1 d . . .
N1 N 1.3295(3) 0.43490(16) 0.01416(13) 0.0661(6) Uani 1 d . . .
N2 N 0.9907(2) 0.76730(14) 0.11209(11) 0.0530(5) Uani 1 d . . .
H2 H 0.9651 0.8014 0.0637 0.064 Uiso 1 calc . . R
N3 N 0.7725(4) 0.96322(18) 0.05353(14) 0.0867(8) Uani 1 d . . .
C1 C 1.2658(3) 0.4817(2) -0.05755(15) 0.0601(6) Uani 1 d . . .
C2 C 1.1412(3) 0.58727(18) -0.07537(14) 0.0563(6) Uani 1 d . . .
H2A H 1.1001 0.6168 -0.1255 0.068 Uiso 1 calc . . R
C3 C 1.0775(3) 0.64933(17) -0.01840(13) 0.0508(6) Uani 1 d . . .
C4 C 1.1428(3) 0.60412(16) 0.05637(13) 0.0480(5) Uani 1 d . . .
C5 C 1.2666(3) 0.49640(18) 0.06764(15) 0.0595(6) Uani 1 d . . .
H5A H 1.3095 0.4642 0.1174 0.071 Uiso 1 calc . . R
C6 C 1.3351(4) 0.4119(2) -0.11804(18) 0.0836(9) Uani 1 d . . .
H6A H 1.4519 0.4171 -0.1393 0.125 Uiso 1 calc . . GR
H6B H 1.2614 0.4427 -0.1608 0.125 Uiso 1 calc . . GR
H6C H 1.3363 0.3314 -0.0927 0.125 Uiso 1 calc . . GR
C7 C 0.8806(4) 0.8004(2) -0.10595(14) 0.0698(7) Uani 1 d . . .
H7A H 0.9707 0.8171 -0.1484 0.105 Uiso 1 calc . . GR
H7B H 0.7906 0.8715 -0.1048 0.105 Uiso 1 calc . . GR
H7C H 0.8315 0.7448 -0.1149 0.105 Uiso 1 calc . . GR
C8 C 1.0910(3) 0.65772(18) 0.12553(13) 0.0512(6) Uani 1 d . . .
C9 C 0.9184(3) 0.83703(18) 0.17036(13) 0.0573(6) Uani 1 d . . .
C10 C 1.0678(5) 0.8512(3) 0.2058(2) 0.0949(10) Uani 1 d . . .
H10A H 1.1366 0.7753 0.2322 0.142 Uiso 1 calc . . GR
H10B H 1.0196 0.8966 0.2438 0.142 Uiso 1 calc . . GR
H10C H 1.1404 0.8905 0.1636 0.142 Uiso 1 calc . . GR
C11 C 0.7966(4) 0.7778(2) 0.23657(16) 0.0859(9) Uani 1 d . . .
H11A H 0.6973 0.7779 0.2140 0.129 Uiso 1 calc . . GR
H11B H 0.7577 0.8198 0.2768 0.129 Uiso 1 calc . . GR
H11C H 0.8586 0.6984 0.2604 0.129 Uiso 1 calc . . GR
C12 C 0.8110(3) 0.95493(18) 0.12457(14) 0.0544(6) Uani 1 d . . .
C13 C 0.7515(4) 1.0507(2) 0.15586(17) 0.0771(8) Uani 1 d . . .
H13 H 0.7795 1.0446 0.2060 0.093 Uiso 1 calc . . R
C14 C 0.6526(4) 1.1537(2) 0.1137(2) 0.0847(9) Uani 1 d . . .
H14 H 0.6119 1.2178 0.1350 0.102 Uiso 1 calc . . R
C15 C 0.6134(4) 1.1625(2) 0.0405(2) 0.0861(9) Uani 1 d . . .
H15 H 0.5466 1.2324 0.0104 0.103 Uiso 1 calc . . R
C16 C 0.6747(5) 1.0663(3) 0.0126(2) 0.1045(12) Uani 1 d . . .
H16 H 0.6478 1.0717 -0.0376 0.125 Uiso 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
O3 C19 1.354(3) . ?
O3 C23 1.424(3) . ?
O4 C24 1.236(2) . ?
N4 C17 1.353(3) . ?
N4 C21 1.333(3) . ?
N5 H5 0.8600 . ?
N5 C24 1.333(3) . ?
N5 C25 1.470(2) . ?
N6 C28 1.330(3) . ?
N6 C32 1.344(3) . ?
C17 C18 1.375(3) . ?
C17 C22 1.492(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.387(3) . ?
C19 C20 1.398(3) . ?
C20 C21 1.387(3) . ?
C20 C24 1.506(3) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C25 C26 1.529(3) . ?
C25 C27 1.536(3) . ?
C25 C28 1.526(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C29 1.388(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.375(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.377(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.371(3) . ?
C32 H32 0.9300 . ?
O1 C3 1.349(2) . ?
O1 C7 1.432(3) . ?
O2 C8 1.242(3) . ?
N1 C1 1.347(3) . ?
N1 C5 1.327(3) . ?
N2 H2 0.8600 . ?
N2 C8 1.330(3) . ?
N2 C9 1.471(3) . ?
N3 C12 1.314(3) . ?
N3 C16 1.347(3) . ?
C1 C2 1.375(3) . ?
C1 C6 1.501(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.383(3) . ?
C3 C4 1.400(3) . ?
C4 C5 1.387(3) . ?
C4 C8 1.499(3) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C9 C10 1.538(4) . ?
C9 C11 1.532(4) . ?
C9 C12 1.520(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.383(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.357(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.351(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.353(4) . ?
C16 H16 0.9300 . ?

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
C19 O3 C23 118.89(17) . . ?
C21 N4 C17 116.5(2) . . ?
C24 N5 H5 117.4 . . ?
C24 N5 C25 125.28(17) . . ?
C25 N5 H5 117.4 . . ?
C28 N6 C32 118.52(19) . . ?
N4 C17 C18 121.8(2) . . ?
N4 C17 C22 116.8(2) . . ?
C18 C17 C22 121.3(2) . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.6(2) . . ?
C19 C18 H18 119.7 . . ?
O3 C19 C18 123.80(19) . . ?
O3 C19 C20 117.58(18) . . ?
C18 C19 C20 118.6(2) . . ?
C19 C20 C24 127.5(2) . . ?
C21 C20 C19 116.13(19) . . ?
C21 C20 C24 116.33(18) . . ?
N4 C21 C20 126.2(2) . . ?
N4 C21 H21 116.9 . . ?
C20 C21 H21 116.9 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O4 C24 N5 123.97(19) . . ?
O4 C24 C20 118.91(19) . . ?
N5 C24 C20 117.05(18) . . ?
N5 C25 C26 109.74(16) . . ?
N5 C25 C27 110.46(16) . . ?
N5 C25 C28 107.06(15) . . ?
C26 C25 C27 111.74(17) . . ?
C28 C25 C26 109.06(17) . . ?
C28 C25 C27 108.64(17) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N6 C28 C25 117.54(17) . . ?
N6 C28 C29 121.6(2) . . ?
C29 C28 C25 120.85(18) . . ?
C28 C29 H29 120.4 . . ?
C30 C29 C28 119.2(2) . . ?
C30 C29 H29 120.4 . . ?
C29 C30 H30 120.3 . . ?
C29 C30 C31 119.3(2) . . ?
C31 C30 H30 120.3 . . ?
C30 C31 H31 120.9 . . ?
C32 C31 C30 118.2(2) . . ?
C32 C31 H31 120.9 . . ?
N6 C32 C31 123.1(2) . . ?
N6 C32 H32 118.5 . . ?
C31 C32 H32 118.5 . . ?
C3 O1 C7 119.14(17) . . ?
C5 N1 C1 116.5(2) . . ?
C8 N2 H2 116.2 . . ?
C8 N2 C9 127.52(19) . . ?
C9 N2 H2 116.2 . . ?
C12 N3 C16 118.6(2) . . ?
N1 C1 C2 122.5(2) . . ?
N1 C1 C6 116.8(2) . . ?
C2 C1 C6 120.7(2) . . ?
C1 C2 H2A 120.1 . . ?
C1 C2 C3 119.7(2) . . ?
C3 C2 H2A 120.1 . . ?
O1 C3 C2 123.3(2) . . ?
O1 C3 C4 117.46(18) . . ?
C2 C3 C4 119.3(2) . . ?
C3 C4 C8 127.31(19) . . ?
C5 C4 C3 115.7(2) . . ?
C5 C4 C8 116.9(2) . . ?
N1 C5 C4 126.2(2) . . ?
N1 C5 H5A 116.9 . . ?
C4 C5 H5A 116.9 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 N2 123.0(2) . . ?
O2 C8 C4 119.66(19) . . ?
N2 C8 C4 117.34(19) . . ?
N2 C9 C10 109.9(2) . . ?
N2 C9 C11 109.78(19) . . ?
N2 C9 C12 106.25(17) . . ?
C11 C9 C10 110.8(2) . . ?
C12 C9 C10 111.2(2) . . ?
C12 C9 C11 108.7(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C9 117.61(18) . . ?
N3 C12 C13 120.1(2) . . ?
C13 C12 C9 122.3(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 121.1 . . ?
C14 C15 C16 117.7(3) . . ?
C16 C15 H15 121.1 . . ?
N3 C16 C15 123.6(3) . . ?
N3 C16 H16 118.2 . . ?
C15 C16 H16 118.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C19 C20 C21 179.70(18) . . . . ?
O3 C19 C20 C24 1.0(3) . . . . ?
N4 C17 C18 C19 -0.8(3) . . . . ?
N5 C25 C28 N6 -4.1(2) . . . . ?
N5 C25 C28 C29 176.68(17) . . . . ?
N6 C28 C29 C30 -1.0(3) . . . . ?
C17 N4 C21 C20 0.6(3) . . . . ?
C17 C18 C19 O3 -179.1(2) . . . . ?
C17 C18 C19 C20 0.9(3) . . . . ?
C18 C19 C20 C21 -0.3(3) . . . . ?
C18 C19 C20 C24 -178.99(19) . . . . ?
C19 C20 C21 N4 -0.4(3) . . . . ?
C19 C20 C24 O4 -161.5(2) . . . . ?
C19 C20 C24 N5 21.5(3) . . . . ?
C21 N4 C17 C18 0.1(3) . . . . ?
C21 N4 C17 C22 -179.0(2) . . . . ?
C21 C20 C24 O4 19.8(3) . . . . ?
C21 C20 C24 N5 -157.25(19) . . . . ?
C22 C17 C18 C19 178.3(2) . . . . ?
C23 O3 C19 C18 -1.4(3) . . . . ?
C23 O3 C19 C20 178.6(2) . . . . ?
C24 N5 C25 C26 -61.6(2) . . . . ?
C24 N5 C25 C27 62.1(2) . . . . ?
C24 N5 C25 C28 -179.79(18) . . . . ?
C24 C20 C21 N4 178.4(2) . . . . ?
C25 N5 C24 O4 -3.6(3) . . . . ?
C25 N5 C24 C20 173.25(17) . . . . ?
C25 C28 C29 C30 178.2(2) . . . . ?
C26 C25 C28 N6 -122.76(19) . . . . ?
C26 C25 C28 C29 58.0(2) . . . . ?
C27 C25 C28 N6 115.2(2) . . . . ?
C27 C25 C28 C29 -64.0(2) . . . . ?
C28 N6 C32 C31 1.2(3) . . . . ?
C28 C29 C30 C31 0.9(3) . . . . ?
C29 C30 C31 C32 0.2(3) . . . . ?
C30 C31 C32 N6 -1.3(3) . . . . ?
C32 N6 C28 C25 -179.24(18) . . . . ?
C32 N6 C28 C29 0.0(3) . . . . ?
O1 C3 C4 C5 178.4(2) . . . . ?
O1 C3 C4 C8 -0.1(3) . . . . ?
N1 C1 C2 C3 0.1(4) . . . . ?
N2 C9 C12 N3 14.1(3) . . . . ?
N2 C9 C12 C13 -167.1(2) . . . . ?
N3 C12 C13 C14 0.3(4) . . . . ?
C1 N1 C5 C4 -0.5(4) . . . . ?
C1 C2 C3 O1 -179.1(2) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
C2 C3 C4 C8 180.0(2) . . . . ?
C3 C4 C5 N1 1.4(4) . . . . ?
C3 C4 C8 O2 170.0(2) . . . . ?
C3 C4 C8 N2 -10.2(3) . . . . ?
C5 N1 C1 C2 -0.3(4) . . . . ?
C5 N1 C1 C6 -179.4(2) . . . . ?
C5 C4 C8 O2 -8.5(3) . . . . ?
C5 C4 C8 N2 171.3(2) . . . . ?
C6 C1 C2 C3 179.1(2) . . . . ?
C7 O1 C3 C2 1.4(4) . . . . ?
C7 O1 C3 C4 -178.5(2) . . . . ?
C8 N2 C9 C10 60.5(3) . . . . ?
C8 N2 C9 C11 -61.7(3) . . . . ?
C8 N2 C9 C12 -179.0(2) . . . . ?
C8 C4 C5 N1 -179.9(2) . . . . ?
C9 N2 C8 O2 -2.5(4) . . . . ?
C9 N2 C8 C4 177.8(2) . . . . ?
C9 C12 C13 C14 -178.5(3) . . . . ?
C10 C9 C12 N3 133.7(3) . . . . ?
C10 C9 C12 C13 -47.5(3) . . . . ?
C11 C9 C12 N3 -104.0(3) . . . . ?
C11 C9 C12 C13 74.8(3) . . . . ?
C12 N3 C16 C15 0.0(5) . . . . ?
C12 C13 C14 C15 -0.5(5) . . . . ?
C13 C14 C15 C16 0.5(5) . . . . ?
C14 C15 C16 N3 -0.3(6) . . . . ?
C16 N3 C12 C9 178.8(3) . . . . ?
C16 N3 C12 C13 0.0(4) . . . . ?

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.036 0.414 0.297 37 8 ' '
2 -0.036 0.586 0.703 37 8 ' '
_platon_squeeze_details          
;
;
