# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1c
_audit_block_doi                 10.5517/cc1kkpvn
_database_code_depnum_ccdc_archive 'CCDC 1446982'
_audit_update_record             
;
2016-01-13 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H14 F N O4'
_chemical_formula_sum            'C25 H14 F N O4'
_chemical_formula_weight         411.37

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.7639(11)
_cell_length_b                   19.413(2)
_cell_length_c                   10.4751(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.6330(10)
_cell_angle_gamma                90.00
_cell_volume                     1912.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6660
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16394
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         27.54
_reflns_number_total             4405
_reflns_number_gt                3537
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0494P)²+0.4914P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4356
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1107
_refine_ls_wR_factor_gt          0.1027
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
C1 C 0.49452(17) 0.95050(8) 0.21695(16) 0.0527(4) Uani 1 1 d . . .
H1A H 0.5303 0.9671 0.3027 0.063 Uiso 1 1 calc R . .
C2 C 0.58663(18) 0.92972(9) 0.14546(19) 0.0614(4) Uani 1 1 d . . .
H2 H 0.6843 0.9328 0.1827 0.074 Uiso 1 1 calc R . .
C3 C 0.53435(19) 0.90438(9) 0.01899(19) 0.0615(4) Uani 1 1 d . . .
H3 H 0.5967 0.8906 -0.0294 0.074 Uiso 1 1 calc R . .
C4 C 0.38890(19) 0.89938(9) -0.03622(17) 0.0574(4) Uani 1 1 d . . .
H4 H 0.3539 0.8815 -0.1212 0.069 Uiso 1 1 calc R . .
C5 C 0.29551(16) 0.92075(8) 0.03421(14) 0.0472(3) Uani 1 1 d . . .
H5 H 0.1979 0.9177 -0.0035 0.057 Uiso 1 1 calc R . .
C6 C 0.34788(15) 0.94672(7) 0.16139(13) 0.0409(3) Uani 1 1 d . . .
C7 C 0.25405(16) 0.97408(7) 0.24009(14) 0.0433(3) Uani 1 1 d . . .
C8 C 0.04178(15) 0.96778(7) 0.32833(13) 0.0384(3) Uani 1 1 d . . .
C9 C 0.09839(14) 0.94983(6) 0.21054(12) 0.0364(3) Uani 1 1 d . . .
H9 H 0.0437 0.9770 0.1351 0.044 Uiso 1 1 calc R . .
C10 C 0.06419(13) 0.87501(6) 0.17688(12) 0.0327(3) Uani 1 1 d . . .
C11 C 0.12450(13) 0.82333(6) 0.25977(12) 0.0336(3) Uani 1 1 d . . .
C12 C 0.23488(14) 0.83647(7) 0.38504(12) 0.0358(3) Uani 1 1 d . . .
C13 C 0.35556(15) 0.79379(8) 0.42241(14) 0.0434(3) Uani 1 1 d . . .
H13 H 0.3680 0.7582 0.3672 0.052 Uiso 1 1 calc R . .
C14 C 0.45446(16) 0.80523(8) 0.54080(16) 0.0502(4) Uani 1 1 d . . .
C15 C 0.44033(18) 0.85683(10) 0.62662(16) 0.0592(4) Uani 1 1 d . . .
H15 H 0.5086 0.8631 0.7069 0.071 Uiso 1 1 calc R . .
C16 C 0.32297(18) 0.89888(9) 0.59080(15) 0.0531(4) Uani 1 1 d . . .
H16 H 0.3116 0.9338 0.6479 0.064 Uiso 1 1 calc R . .
C17 C 0.22088(14) 0.89004(7) 0.47021(12) 0.0387(3) Uani 1 1 d . . .
C18 C -0.04769(14) 0.86130(7) 0.05005(12) 0.0364(3) Uani 1 1 d . . .
C19 C -0.09342(13) 0.78929(7) 0.01761(12) 0.0360(3) Uani 1 1 d . . .
C20 C -0.19452(16) 0.77432(8) -0.10126(14) 0.0475(3) Uani 1 1 d . . .
H20 H -0.2299 0.8092 -0.1621 0.057 Uiso 1 1 calc R . .
C21 C -0.24189(19) 0.70728(9) -0.12813(17) 0.0609(5) Uani 1 1 d . . .
H21 H -0.3082 0.6970 -0.2078 0.073 Uiso 1 1 calc R . .
C22 C -0.1911(2) 0.65547(9) -0.03715(18) 0.0629(5) Uani 1 1 d . . .
H22 H -0.2259 0.6109 -0.0549 0.075 Uiso 1 1 calc R . .
C23 C -0.08904(17) 0.66932(8) 0.07992(16) 0.0504(4) Uani 1 1 d . . .
H23 H -0.0544 0.6342 0.1403 0.060 Uiso 1 1 calc R . .
C24 C -0.03833(14) 0.73633(7) 0.10681(13) 0.0373(3) Uani 1 1 d . . .
C25 C 0.07458(14) 0.75023(7) 0.23088(13) 0.0384(3) Uani 1 1 d . . .
F1 F 0.57021(10) 0.76349(6) 0.57586(10) 0.0710(3) Uani 1 1 d . . .
N1 N 0.10335(13) 0.93506(6) 0.44330(11) 0.0407(3) Uani 1 1 d . . .
H1 H 0.0664 0.9426 0.5078 0.049 Uiso 1 1 calc R . .
O1 O 0.29529(14) 1.01756(6) 0.32484(12) 0.0668(4) Uani 1 1 d . . .
O2 O -0.05577(12) 1.00910(5) 0.31919(10) 0.0508(3) Uani 1 1 d . . .
O3 O -0.09957(12) 0.90903(5) -0.02298(11) 0.0569(3) Uani 1 1 d . . .
O4 O 0.12228(13) 0.70440(5) 0.30926(12) 0.0631(3) Uani 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
C1 C2 1.377(2) . ?
C1 C6 1.395(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.376(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.486(2) . ?
C7 O1 1.2125(17) . ?
C7 C9 1.541(2) . ?
C8 O2 1.2291(16) . ?
C8 N1 1.3509(17) . ?
C8 C9 1.5222(18) . ?
C9 C10 1.5106(17) . ?
C9 H9 0.9800 . ?
C10 C11 1.3534(17) . ?
C10 C18 1.4990(17) . ?
C11 C12 1.4786(17) . ?
C11 C25 1.5045(18) . ?
C12 C17 1.4008(18) . ?
C12 C13 1.4069(19) . ?
C13 C14 1.369(2) . ?
C13 H13 0.9300 . ?
C14 F1 1.3583(17) . ?
C14 C15 1.377(2) . ?
C15 C16 1.374(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.3929(19) . ?
C16 H16 0.9300 . ?
C17 N1 1.4091(17) . ?
C18 O3 1.2212(16) . ?
C18 C19 1.4791(18) . ?
C19 C20 1.3953(18) . ?
C19 C24 1.3958(18) . ?
C20 C21 1.385(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.382(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.382(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.3934(19) . ?
C23 H23 0.9300 . ?
C24 C25 1.4849(18) . ?
C25 O4 1.2150(16) . ?
N1 H1 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.35(16) . . ?
C2 C1 H1A 119.8 . . ?
C6 C1 H1A 119.8 . . ?
C3 C2 C1 120.08(16) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 119.98(16) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.39(16) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.76(15) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 119.43(14) . . ?
C5 C6 C7 122.69(13) . . ?
C1 C6 C7 117.83(13) . . ?
O1 C7 C6 121.48(14) . . ?
O1 C7 C9 118.35(13) . . ?
C6 C7 C9 120.11(12) . . ?
O2 C8 N1 121.71(12) . . ?
O2 C8 C9 121.96(12) . . ?
N1 C8 C9 116.33(11) . . ?
C10 C9 C8 107.67(10) . . ?
C10 C9 C7 119.00(11) . . ?
C8 C9 C7 108.73(11) . . ?
C10 C9 H9 107.0 . . ?
C8 C9 H9 107.0 . . ?
C7 C9 H9 107.0 . . ?
C11 C10 C18 121.61(11) . . ?
C11 C10 C9 122.17(11) . . ?
C18 C10 C9 116.10(11) . . ?
C10 C11 C12 121.91(11) . . ?
C10 C11 C25 120.58(11) . . ?
C12 C11 C25 117.41(11) . . ?
C17 C12 C13 118.57(12) . . ?
C17 C12 C11 121.36(12) . . ?
C13 C12 C11 120.06(12) . . ?
C14 C13 C12 119.33(13) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
F1 C14 C13 118.72(14) . . ?
F1 C14 C15 118.66(13) . . ?
C13 C14 C15 122.61(14) . . ?
C16 C15 C14 118.46(14) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
C15 C16 C17 120.98(14) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C12 120.02(13) . . ?
C16 C17 N1 116.76(12) . . ?
C12 C17 N1 123.16(12) . . ?
O3 C18 C19 121.64(12) . . ?
O3 C18 C10 120.05(12) . . ?
C19 C18 C10 118.31(11) . . ?
C20 C19 C24 119.76(13) . . ?
C20 C19 C18 119.94(12) . . ?
C24 C19 C18 120.29(11) . . ?
C21 C20 C19 119.63(14) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C22 C21 C20 120.38(14) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C21 120.59(15) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 119.53(15) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C23 C24 C19 120.03(12) . . ?
C23 C24 C25 119.08(12) . . ?
C19 C24 C25 120.89(11) . . ?
O4 C25 C24 121.16(12) . . ?
O4 C25 C11 120.68(12) . . ?
C24 C25 C11 118.12(11) . . ?
C8 N1 C17 127.78(11) . . ?
C8 N1 H1 116.1 . . ?
C17 N1 H1 116.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.86 2.07 2.8642(15) 153.7 3_576

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_1e
_audit_block_doi                 10.5517/cc1kkpwp
_database_code_depnum_ccdc_archive 'CCDC 1446983'
_audit_update_record             
;
2016-01-13 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H17 N O5'
_chemical_formula_sum            'C26 H17 N O5'
_chemical_formula_weight         423.41

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           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   11.2312(12)
_cell_length_b                   16.239(2)
_cell_length_c                   22.524(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4108.0(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9832
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      25.20

_exptl_crystal_description       bolock
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1760
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37605
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_sigmaI/netI    0.0769
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         27.57
_reflns_number_total             9409
_reflns_number_gt                5844
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0445P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         9409
_refine_ls_number_parameters     579
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1101
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.0967
_refine_ls_wR_factor_gt          0.0828
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.95945(19) 0.75043(12) 0.59474(9) 0.0341(5) Uani 1 1 d . . .
C2 C 1.0409(2) 0.80681(14) 0.57188(9) 0.0452(6) Uani 1 1 d . . .
H2A H 1.1173 0.8097 0.5876 0.054 Uiso 1 1 calc R . .
C3 C 1.0087(2) 0.85821(14) 0.52612(10) 0.0523(7) Uani 1 1 d . . .
H3 H 1.0634 0.8955 0.5107 0.063 Uiso 1 1 calc R . .
C4 C 0.8945(2) 0.85426(14) 0.50298(10) 0.0482(6) Uani 1 1 d . . .
H4 H 0.8731 0.8888 0.4718 0.058 Uiso 1 1 calc R . .
C5 C 0.8128(2) 0.79983(13) 0.52567(9) 0.0402(5) Uani 1 1 d . . .
H5 H 0.7364 0.7980 0.5098 0.048 Uiso 1 1 calc R . .
C6 C 0.84319(18) 0.74689(12) 0.57261(8) 0.0308(5) Uani 1 1 d . . .
C7 C 0.98261(17) 0.62123(14) 0.65242(9) 0.0336(5) Uani 1 1 d . . .
C8 C 0.89960(17) 0.57640(12) 0.61036(9) 0.0314(5) Uani 1 1 d . . .
H8 H 0.8936 0.5195 0.6245 0.038 Uiso 1 1 calc R . .
C9 C 0.95082(19) 0.57272(12) 0.54684(9) 0.0352(5) Uani 1 1 d . . .
C10 C 0.87116(18) 0.54416(12) 0.49882(9) 0.0338(5) Uani 1 1 d . . .
C11 C 0.8880(2) 0.57568(13) 0.44214(9) 0.0408(6) Uani 1 1 d . . .
H11 H 0.9493 0.6131 0.4356 0.049 Uiso 1 1 calc R . .
C12 C 0.81619(19) 0.55289(13) 0.39554(9) 0.0416(5) Uani 1 1 d . . .
H12 H 0.8275 0.5758 0.3581 0.050 Uiso 1 1 calc R . .
C13 C 0.72681(19) 0.49555(14) 0.40479(9) 0.0395(5) Uani 1 1 d . . .
C14 C 0.6564(2) 0.50958(16) 0.30507(10) 0.0601(7) Uani 1 1 d . . .
H14A H 0.6415 0.5674 0.3098 0.090 Uiso 1 1 calc R . .
H14B H 0.5979 0.4863 0.2789 0.090 Uiso 1 1 calc R . .
H14C H 0.7343 0.5017 0.2885 0.090 Uiso 1 1 calc R . .
C15 C 0.7114(2) 0.46085(13) 0.46030(9) 0.0425(5) Uani 1 1 d . . .
H15 H 0.6535 0.4207 0.4661 0.051 Uiso 1 1 calc R . .
C16 C 0.78160(19) 0.48571(13) 0.50701(9) 0.0407(5) Uani 1 1 d . . .
H16 H 0.7692 0.4633 0.5445 0.049 Uiso 1 1 calc R . .
C17 C 0.77647(17) 0.61399(12) 0.61574(8) 0.0290(5) Uani 1 1 d . . .
C18 C 0.68436(19) 0.56078(13) 0.64311(9) 0.0351(5) Uani 1 1 d . . .
C19 C 0.56158(18) 0.59236(14) 0.64845(9) 0.0369(5) Uani 1 1 d . . .
C20 C 0.4708(2) 0.54194(16) 0.66968(11) 0.0543(6) Uani 1 1 d . . .
H20 H 0.4874 0.4882 0.6814 0.065 Uiso 1 1 calc R . .
C21 C 0.3559(2) 0.57199(18) 0.67328(12) 0.0611(7) Uani 1 1 d . . .
H21 H 0.2949 0.5381 0.6868 0.073 Uiso 1 1 calc R . .
C22 C 0.3314(2) 0.65161(17) 0.65698(10) 0.0541(7) Uani 1 1 d . . .
H22 H 0.2537 0.6711 0.6592 0.065 Uiso 1 1 calc R . .
C23 C 0.42037(19) 0.70277(16) 0.63753(9) 0.0448(6) Uani 1 1 d . . .
H23 H 0.4034 0.7572 0.6278 0.054 Uiso 1 1 calc R . .
C24 C 0.53596(19) 0.67309(13) 0.63243(8) 0.0344(5) Uani 1 1 d . . .
C25 C 0.63099(19) 0.72774(14) 0.60965(9) 0.0359(5) Uani 1 1 d . . .
C26 C 0.75276(17) 0.69221(13) 0.59888(8) 0.0306(5) Uani 1 1 d . . .
C27 C 0.26760(19) 0.37273(13) 0.32915(9) 0.0377(5) Uani 1 1 d . . .
C28 C 0.3370(2) 0.43066(15) 0.35744(11) 0.0603(7) Uani 1 1 d . . .
H28 H 0.4170 0.4358 0.3475 0.072 Uiso 1 1 calc R . .
C29 C 0.2889(3) 0.48088(19) 0.40025(13) 0.0785(9) Uani 1 1 d . . .
H29 H 0.3360 0.5207 0.4184 0.094 Uiso 1 1 calc R . .
C30 C 0.1721(3) 0.47262(18) 0.41624(13) 0.0729(8) Uani 1 1 d . . .
H30 H 0.1405 0.5057 0.4460 0.088 Uiso 1 1 calc R . .
C31 C 0.1017(2) 0.41588(15) 0.38853(11) 0.0547(7) Uani 1 1 d . . .
H31 H 0.0222 0.4113 0.3997 0.066 Uiso 1 1 calc R . .
C32 C 0.14597(19) 0.36413(13) 0.34359(9) 0.0383(5) Uani 1 1 d . . .
C33 C 0.31234(18) 0.24701(13) 0.27132(9) 0.0301(5) Uani 1 1 d . . .
C34 C 0.22867(17) 0.19807(13) 0.30988(8) 0.0327(5) Uani 1 1 d . . .
H34 H 0.2322 0.1410 0.2958 0.039 Uiso 1 1 calc R . .
C35 C 0.25661(19) 0.19579(13) 0.37682(9) 0.0375(5) Uani 1 1 d . . .
C36 C 0.38204(19) 0.18580(13) 0.39577(9) 0.0384(5) Uani 1 1 d . . .
C37 C 0.4651(2) 0.14269(14) 0.36246(10) 0.0422(6) Uani 1 1 d . . .
H37 H 0.4434 0.1219 0.3255 0.051 Uiso 1 1 calc R . .
C38 C 0.5792(2) 0.13007(15) 0.38310(11) 0.0521(6) Uani 1 1 d . . .
H38 H 0.6331 0.0993 0.3610 0.062 Uiso 1 1 calc R . .
C39 C 0.6125(2) 0.16329(17) 0.43657(12) 0.0586(7) Uani 1 1 d . . .
C40 C 0.8098(3) 0.1084(3) 0.42972(18) 0.1306(16) Uani 1 1 d . . .
H40A H 0.7791 0.0537 0.4244 0.196 Uiso 1 1 calc R . .
H40B H 0.8819 0.1061 0.4526 0.196 Uiso 1 1 calc R . .
H40C H 0.8261 0.1325 0.3917 0.196 Uiso 1 1 calc R . .
C41 C 0.5312(3) 0.20741(17) 0.47011(12) 0.0692(8) Uani 1 1 d . . .
H41 H 0.5543 0.2307 0.5060 0.083 Uiso 1 1 calc R . .
C42 C 0.4167(2) 0.21671(16) 0.45038(11) 0.0571(7) Uani 1 1 d . . .
H42 H 0.3615 0.2441 0.4740 0.069 Uiso 1 1 calc R . .
C43 C 0.10481(18) 0.22861(13) 0.29703(8) 0.0329(5) Uani 1 1 d . . .
C44 C 0.0292(2) 0.17283(15) 0.26123(9) 0.0395(5) Uani 1 1 d . . .
C45 C -0.0999(2) 0.19137(17) 0.25685(9) 0.0479(6) Uani 1 1 d . . .
C46 C -0.1768(2) 0.13410(19) 0.23248(11) 0.0655(8) Uani 1 1 d . . .
H46 H -0.1481 0.0847 0.2173 0.079 Uiso 1 1 calc R . .
C47 C -0.2986(3) 0.1520(3) 0.23122(14) 0.0849(10) Uani 1 1 d . . .
H47 H -0.3518 0.1143 0.2152 0.102 Uiso 1 1 calc R . .
C48 C -0.3395(3) 0.2251(3) 0.25363(15) 0.0857(11) Uani 1 1 d . . .
H48 H -0.4209 0.2357 0.2536 0.103 Uiso 1 1 calc R . .
C49 C -0.2632(2) 0.2831(2) 0.27607(12) 0.0693(8) Uani 1 1 d . . .
H49 H -0.2922 0.3332 0.2899 0.083 Uiso 1 1 calc R . .
C50 C -0.1418(2) 0.26618(17) 0.27799(10) 0.0494(6) Uani 1 1 d . . .
C51 C -0.0571(2) 0.32997(17) 0.29974(10) 0.0492(6) Uani 1 1 d . . .
C52 C 0.06809(17) 0.30447(14) 0.31380(9) 0.0366(5) Uani 1 1 d . . .
N1 N 0.99936(14) 0.70189(11) 0.64279(7) 0.0356(4) Uani 1 1 d . . .
H1 H 1.0398 0.7275 0.6694 0.043 Uiso 1 1 calc R . .
N2 N 0.32343(15) 0.32725(10) 0.28332(7) 0.0349(4) Uani 1 1 d . . .
H2 H 0.3702 0.3546 0.2604 0.042 Uiso 1 1 calc R . .
O1 O 1.02902(13) 0.58580(9) 0.69494(6) 0.0462(4) Uani 1 1 d . . .
O2 O 1.05393(14) 0.59215(10) 0.53822(7) 0.0511(4) Uani 1 1 d . . .
O3 O 0.64985(14) 0.46980(10) 0.36169(6) 0.0512(4) Uani 1 1 d . . .
O4 O 0.70961(14) 0.49143(10) 0.65924(8) 0.0584(5) Uani 1 1 d . . .
O5 O 0.61242(14) 0.80067(10) 0.60156(7) 0.0560(4) Uani 1 1 d . . .
O6 O 0.36436(12) 0.21499(8) 0.22894(6) 0.0392(4) Uani 1 1 d . . .
O7 O 0.17599(15) 0.19937(11) 0.41246(7) 0.0576(5) Uani 1 1 d . . .
O8 O 0.72454(18) 0.15705(14) 0.46007(9) 0.0911(7) Uani 1 1 d . . .
O9 O 0.07288(15) 0.11273(11) 0.23709(7) 0.0585(5) Uani 1 1 d . . .
O10 O -0.08920(16) 0.40124(13) 0.30493(9) 0.0766(6) Uani 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
C1 C2 1.393(3) . ?
C1 C6 1.399(3) . ?
C1 N1 1.412(3) . ?
C2 C3 1.375(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.405(3) . ?
C5 H5 0.9300 . ?
C6 C26 1.473(3) . ?
C7 O1 1.233(2) . ?
C7 N1 1.341(3) . ?
C7 C8 1.515(3) . ?
C8 C17 1.517(3) . ?
C8 C9 1.543(3) . ?
C8 H8 0.9800 . ?
C9 O2 1.216(2) . ?
C9 C10 1.478(3) . ?
C10 C11 1.388(3) . ?
C10 C16 1.395(3) . ?
C11 C12 1.375(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(3) . ?
C12 H12 0.9300 . ?
C13 O3 1.365(2) . ?
C13 C15 1.382(3) . ?
C14 O3 1.431(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.375(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C26 1.352(3) . ?
C17 C18 1.482(3) . ?
C18 O4 1.217(2) . ?
C18 C19 1.476(3) . ?
C19 C24 1.390(3) . ?
C19 C20 1.392(3) . ?
C20 C21 1.382(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.372(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.371(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.390(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.480(3) . ?
C25 O5 1.216(2) . ?
C25 C26 1.504(3) . ?
C27 C28 1.378(3) . ?
C27 C32 1.411(3) . ?
C27 N2 1.416(3) . ?
C28 C29 1.374(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.367(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.365(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.406(3) . ?
C31 H31 0.9300 . ?
C32 C52 1.468(3) . ?
C33 O6 1.234(2) . ?
C33 N2 1.336(3) . ?
C33 C34 1.506(3) . ?
C34 C43 1.505(3) . ?
C34 C35 1.540(3) . ?
C34 H34 0.9800 . ?
C35 O7 1.211(2) . ?
C35 C36 1.481(3) . ?
C36 C42 1.384(3) . ?
C36 C37 1.387(3) . ?
C37 C38 1.379(3) . ?
C37 H37 0.9300 . ?
C38 C39 1.372(3) . ?
C38 H38 0.9300 . ?
C39 O8 1.369(3) . ?
C39 C41 1.385(4) . ?
C40 O8 1.417(4) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 C42 1.369(3) . ?
C41 H41 0.9300 . ?
C42 H42 0.9300 . ?
C43 C52 1.353(3) . ?
C43 C44 1.480(3) . ?
C44 O9 1.220(3) . ?
C44 C45 1.485(3) . ?
C45 C46 1.382(3) . ?
C45 C50 1.387(3) . ?
C46 C47 1.399(4) . ?
C46 H46 0.9300 . ?
C47 C48 1.369(5) . ?
C47 H47 0.9300 . ?
C48 C49 1.369(4) . ?
C48 H48 0.9300 . ?
C49 C50 1.391(3) . ?
C49 H49 0.9300 . ?
C50 C51 1.490(4) . ?
C51 O10 1.218(3) . ?
C51 C52 1.499(3) . ?
N1 H1 0.8600 . ?
N2 H2 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.54(19) . . ?
C2 C1 N1 116.23(19) . . ?
C6 C1 N1 123.14(18) . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.04(19) . . ?
C1 C6 C26 121.68(17) . . ?
C5 C6 C26 120.23(19) . . ?
O1 C7 N1 121.47(19) . . ?
O1 C7 C8 121.4(2) . . ?
N1 C7 C8 117.03(18) . . ?
C7 C8 C17 108.53(16) . . ?
C7 C8 C9 111.65(16) . . ?
C17 C8 C9 115.44(17) . . ?
C7 C8 H8 106.9 . . ?
C17 C8 H8 106.9 . . ?
C9 C8 H8 106.9 . . ?
O2 C9 C10 122.76(19) . . ?
O2 C9 C8 119.53(19) . . ?
C10 C9 C8 117.71(18) . . ?
C11 C10 C16 118.07(19) . . ?
C11 C10 C9 118.34(19) . . ?
C16 C10 C9 123.57(19) . . ?
C12 C11 C10 121.5(2) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 119.43(19) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
O3 C13 C15 116.03(19) . . ?
O3 C13 C12 123.90(19) . . ?
C15 C13 C12 120.1(2) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C13 120.0(2) . . ?
C16 C15 H15 120.0 . . ?
C13 C15 H15 120.0 . . ?
C15 C16 C10 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
C10 C16 H16 119.6 . . ?
C26 C17 C18 121.81(18) . . ?
C26 C17 C8 122.35(18) . . ?
C18 C17 C8 115.79(17) . . ?
O4 C18 C19 121.0(2) . . ?
O4 C18 C17 120.07(19) . . ?
C19 C18 C17 118.90(18) . . ?
C24 C19 C20 119.5(2) . . ?
C24 C19 C18 120.00(19) . . ?
C20 C19 C18 120.5(2) . . ?
C21 C20 C19 119.7(2) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C22 C21 C20 120.3(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 120.7(2) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 119.8(2) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C19 119.9(2) . . ?
C23 C24 C25 119.6(2) . . ?
C19 C24 C25 120.43(19) . . ?
O5 C25 C24 120.81(19) . . ?
O5 C25 C26 120.4(2) . . ?
C24 C25 C26 118.79(18) . . ?
C17 C26 C6 122.90(18) . . ?
C17 C26 C25 119.61(18) . . ?
C6 C26 C25 117.42(18) . . ?
C28 C27 C32 120.6(2) . . ?
C28 C27 N2 116.3(2) . . ?
C32 C27 N2 123.03(19) . . ?
C29 C28 C27 120.5(2) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C30 C29 C28 120.3(3) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C31 C30 C29 120.1(3) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 C32 121.9(2) . . ?
C30 C31 H31 119.1 . . ?
C32 C31 H31 119.1 . . ?
C31 C32 C27 116.7(2) . . ?
C31 C32 C52 120.8(2) . . ?
C27 C32 C52 122.48(19) . . ?
O6 C33 N2 121.55(19) . . ?
O6 C33 C34 121.27(18) . . ?
N2 C33 C34 117.11(18) . . ?
C43 C34 C33 106.97(16) . . ?
C43 C34 C35 112.61(16) . . ?
C33 C34 C35 116.74(17) . . ?
C43 C34 H34 106.6 . . ?
C33 C34 H34 106.6 . . ?
C35 C34 H34 106.6 . . ?
O7 C35 C36 121.68(18) . . ?
O7 C35 C34 119.68(19) . . ?
C36 C35 C34 118.60(18) . . ?
C42 C36 C37 118.3(2) . . ?
C42 C36 C35 119.0(2) . . ?
C37 C36 C35 122.62(19) . . ?
C38 C37 C36 121.2(2) . . ?
C38 C37 H37 119.4 . . ?
C36 C37 H37 119.4 . . ?
C39 C38 C37 119.4(2) . . ?
C39 C38 H38 120.3 . . ?
C37 C38 H38 120.3 . . ?
O8 C39 C38 124.1(2) . . ?
O8 C39 C41 115.7(2) . . ?
C38 C39 C41 120.2(2) . . ?
O8 C40 H40A 109.5 . . ?
O8 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
O8 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C42 C41 C39 120.0(2) . . ?
C42 C41 H41 120.0 . . ?
C39 C41 H41 120.0 . . ?
C41 C42 C36 120.8(2) . . ?
C41 C42 H42 119.6 . . ?
C36 C42 H42 119.6 . . ?
C52 C43 C44 122.30(19) . . ?
C52 C43 C34 121.88(18) . . ?
C44 C43 C34 115.68(19) . . ?
O9 C44 C43 120.1(2) . . ?
O9 C44 C45 121.7(2) . . ?
C43 C44 C45 118.2(2) . . ?
C46 C45 C50 120.9(2) . . ?
C46 C45 C44 120.0(3) . . ?
C50 C45 C44 119.1(2) . . ?
C45 C46 C47 118.6(3) . . ?
C45 C46 H46 120.7 . . ?
C47 C46 H46 120.7 . . ?
C48 C47 C46 120.1(3) . . ?
C48 C47 H47 120.0 . . ?
C46 C47 H47 120.0 . . ?
C49 C48 C47 121.4(3) . . ?
C49 C48 H48 119.3 . . ?
C47 C48 H48 119.3 . . ?
C48 C49 C50 119.3(3) . . ?
C48 C49 H49 120.3 . . ?
C50 C49 H49 120.3 . . ?
C45 C50 C49 119.6(3) . . ?
C45 C50 C51 120.4(2) . . ?
C49 C50 C51 119.9(3) . . ?
O10 C51 C50 120.2(2) . . ?
O10 C51 C52 121.3(2) . . ?
C50 C51 C52 118.5(2) . . ?
C43 C52 C32 123.16(19) . . ?
C43 C52 C51 118.6(2) . . ?
C32 C52 C51 118.2(2) . . ?
C7 N1 C1 128.65(17) . . ?
C7 N1 H1 115.7 . . ?
C1 N1 H1 115.7 . . ?
C33 N2 C27 127.95(18) . . ?
C33 N2 H2 116.0 . . ?
C27 N2 H2 116.0 . . ?
C13 O3 C14 117.54(17) . . ?
C39 O8 C40 118.4(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O6 0.86 1.96 2.816(2) 178.5 2_665
N2 H2 O1 0.86 2.10 2.950(2) 172.2 2_664

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_1k
_audit_block_doi                 10.5517/cc1kkpxq
_database_code_depnum_ccdc_archive 'CCDC 1446984'
_audit_update_record             
;
2016-01-13 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H13 F2 N O4'
_chemical_formula_sum            'C25 H13 F2 N O4'
_chemical_formula_weight         429.36

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   10.033(4)
_cell_length_b                   19.091(8)
_cell_length_c                   10.544(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.453(11)
_cell_angle_gamma                90.00
_cell_volume                     1926.6(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1785
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      21.88

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10385
_diffrn_reflns_av_R_equivalents  0.0954
_diffrn_reflns_av_sigmaI/netI    0.1437
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3281
_reflns_number_gt                1564
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0634P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3281
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1723
_refine_ls_R_factor_gt           0.0605
_refine_ls_wR_factor_ref         0.1387
_refine_ls_wR_factor_gt          0.1167
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_restrained_S_all      0.917
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2179(4) 0.11209(17) 0.4761(3) 0.0354(9) Uani 1 1 d . . .
C2 C 0.3175(4) 0.1039(2) 0.5987(4) 0.0503(11) Uani 1 1 d . . .
H2 H 0.3053 0.0696 0.6569 0.060 Uiso 1 1 calc R . .
C3 C 0.4337(4) 0.1459(2) 0.6352(4) 0.0587(11) Uani 1 1 d . . .
H3 H 0.5002 0.1408 0.7178 0.070 Uiso 1 1 calc R . .
C4 C 0.4490(4) 0.1953(2) 0.5470(4) 0.0490(10) Uani 1 1 d . . .
C5 C 0.3527(4) 0.20666(18) 0.4287(3) 0.0420(10) Uani 1 1 d . . .
H5 H 0.3661 0.2421 0.3733 0.050 Uiso 1 1 calc R . .
C6 C 0.2326(4) 0.16515(17) 0.3892(3) 0.0330(9) Uani 1 1 d . . .
C7 C 0.0395(4) 0.03373(19) 0.3309(3) 0.0383(9) Uani 1 1 d . . .
C8 C 0.0964(3) 0.04977(16) 0.2162(3) 0.0330(9) Uani 1 1 d . . .
H8 H 0.0421 0.0219 0.1402 0.040 Uiso 1 1 calc R . .
C9 C 0.2478(4) 0.02408(18) 0.2516(3) 0.0381(9) Uani 1 1 d . . .
C10 C 0.3393(4) 0.04961(17) 0.1749(3) 0.0350(9) Uani 1 1 d . . .
C11 C 0.4828(4) 0.04549(17) 0.2326(4) 0.0458(10) Uani 1 1 d . . .
H11 H 0.5184 0.0287 0.3190 0.055 Uiso 1 1 calc R . .
C12 C 0.5732(4) 0.06584(19) 0.1639(4) 0.0483(10) Uani 1 1 d . . .
H12 H 0.6694 0.0625 0.2023 0.058 Uiso 1 1 calc R . .
C13 C 0.5182(4) 0.09099(19) 0.0384(4) 0.0493(11) Uani 1 1 d . . .
C14 C 0.3783(4) 0.09647(18) -0.0224(4) 0.0499(11) Uani 1 1 d . . .
H14 H 0.3444 0.1140 -0.1084 0.060 Uiso 1 1 calc R . .
C15 C 0.2886(4) 0.07559(17) 0.0460(3) 0.0425(10) Uani 1 1 d . . .
H15 H 0.1927 0.0788 0.0058 0.051 Uiso 1 1 calc R . .
C16 C 0.0654(3) 0.12598(17) 0.1796(3) 0.0302(8) Uani 1 1 d . . .
C17 C -0.0405(3) 0.14018(19) 0.0484(3) 0.0329(9) Uani 1 1 d . . .
C18 C -0.0912(3) 0.21253(17) 0.0171(3) 0.0303(8) Uani 1 1 d . . .
C19 C -0.1933(4) 0.22713(19) -0.1000(3) 0.0442(10) Uani 1 1 d . . .
H19 H -0.2269 0.1919 -0.1623 0.053 Uiso 1 1 calc R . .
C20 C -0.2453(4) 0.2938(2) -0.1247(4) 0.0594(12) Uani 1 1 d . . .
H20 H -0.3133 0.3038 -0.2044 0.071 Uiso 1 1 calc R . .
C21 C -0.1972(4) 0.3460(2) -0.0318(4) 0.0611(12) Uani 1 1 d . . .
H21 H -0.2354 0.3907 -0.0479 0.073 Uiso 1 1 calc R . .
C22 C -0.0937(4) 0.33237(19) 0.0840(4) 0.0475(10) Uani 1 1 d . . .
H22 H -0.0605 0.3678 0.1459 0.057 Uiso 1 1 calc R . .
C23 C -0.0386(3) 0.26507(17) 0.1083(3) 0.0329(9) Uani 1 1 d . . .
C24 C 0.0765(4) 0.25212(19) 0.2312(3) 0.0403(9) Uani 1 1 d . . .
C25 C 0.1250(3) 0.17835(17) 0.2623(3) 0.0309(8) Uani 1 1 d . . .
F1 F 0.5661(2) 0.23606(12) 0.5830(2) 0.0722(7) Uani 1 1 d . . .
F2 F 0.6065(2) 0.11126(12) -0.0294(2) 0.0776(8) Uani 1 1 d . . .
N1 N 0.1008(3) 0.06726(14) 0.4467(3) 0.0401(8) Uani 1 1 d . . .
H1 H 0.0642 0.0605 0.5097 0.048 Uiso 1 1 calc R . .
O1 O -0.0581(3) -0.00702(12) 0.3199(2) 0.0481(7) Uani 1 1 d . . .
O2 O 0.2880(3) -0.01836(13) 0.3398(3) 0.0602(8) Uani 1 1 d . . .
O3 O -0.0817(2) 0.09225(12) -0.0302(2) 0.0516(7) Uani 1 1 d . . .
O4 O 0.1269(3) 0.29921(13) 0.3092(3) 0.0665(8) Uani 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
C1 C2 1.385(5) . ?
C1 C6 1.403(4) . ?
C1 N1 1.411(4) . ?
C2 C3 1.371(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.347(5) . ?
C4 F1 1.365(4) . ?
C5 C6 1.397(4) . ?
C5 H5 0.9300 . ?
C6 C25 1.467(4) . ?
C7 O1 1.228(4) . ?
C7 N1 1.353(4) . ?
C7 C8 1.515(4) . ?
C8 C16 1.514(4) . ?
C8 C9 1.533(4) . ?
C8 H8 0.9800 . ?
C9 O2 1.208(4) . ?
C9 C10 1.476(5) . ?
C10 C11 1.386(4) . ?
C10 C15 1.392(4) . ?
C11 C12 1.376(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.360(5) . ?
C12 H12 0.9300 . ?
C13 F2 1.351(4) . ?
C13 C14 1.360(5) . ?
C14 C15 1.371(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C25 1.344(4) . ?
C16 C17 1.495(4) . ?
C17 O3 1.221(3) . ?
C17 C18 1.475(4) . ?
C18 C19 1.376(4) . ?
C18 C23 1.380(4) . ?
C19 C20 1.370(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.379(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.370(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.392(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.476(5) . ?
C24 O4 1.221(4) . ?
C24 C25 1.494(5) . ?
N1 H1 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.2(3) . . ?
C2 C1 N1 117.2(3) . . ?
C6 C1 N1 122.5(3) . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 118.2(3) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C5 C4 C3 123.1(4) . . ?
C5 C4 F1 118.9(3) . . ?
C3 C4 F1 117.9(3) . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 117.7(3) . . ?
C5 C6 C25 120.5(3) . . ?
C1 C6 C25 121.8(3) . . ?
O1 C7 N1 121.2(3) . . ?
O1 C7 C8 122.2(3) . . ?
N1 C7 C8 116.5(3) . . ?
C16 C8 C7 107.5(2) . . ?
C16 C8 C9 118.8(3) . . ?
C7 C8 C9 109.0(3) . . ?
C16 C8 H8 107.0 . . ?
C7 C8 H8 107.0 . . ?
C9 C8 H8 107.0 . . ?
O2 C9 C10 121.6(3) . . ?
O2 C9 C8 118.6(3) . . ?
C10 C9 C8 119.7(3) . . ?
C11 C10 C15 118.4(3) . . ?
C11 C10 C9 118.4(3) . . ?
C15 C10 C9 123.2(3) . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C13 C12 C11 118.2(4) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
F2 C13 C12 118.5(4) . . ?
F2 C13 C14 118.5(4) . . ?
C12 C13 C14 123.1(3) . . ?
C13 C14 C15 118.5(3) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
C14 C15 C10 120.8(3) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C25 C16 C17 121.4(3) . . ?
C25 C16 C8 122.1(3) . . ?
C17 C16 C8 116.4(3) . . ?
O3 C17 C18 121.8(3) . . ?
O3 C17 C16 119.6(3) . . ?
C18 C17 C16 118.6(3) . . ?
C19 C18 C23 120.3(3) . . ?
C19 C18 C17 120.3(3) . . ?
C23 C18 C17 119.4(3) . . ?
C20 C19 C18 119.8(4) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.3(4) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 120.4(4) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 119.5(4) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C18 C23 C22 119.7(3) . . ?
C18 C23 C24 121.7(3) . . ?
C22 C23 C24 118.6(3) . . ?
O4 C24 C23 121.7(3) . . ?
O4 C24 C25 120.3(3) . . ?
C23 C24 C25 117.9(3) . . ?
C16 C25 C6 121.8(3) . . ?
C16 C25 C24 120.4(3) . . ?
C6 C25 C24 117.7(3) . . ?
C7 N1 C1 127.5(3) . . ?
C7 N1 H1 116.2 . . ?
C1 N1 H1 116.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 2.08 2.863(3) 150.5 3_556

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_1l
_audit_block_doi                 10.5517/cc1kkpyr
_database_code_depnum_ccdc_archive 'CCDC 1446985'
_audit_update_record             
;
2016-01-13 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H13 Cl F N O4'
_chemical_formula_sum            'C25 H13 Cl F N O4'
_chemical_formula_weight         445.81

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9815(12)
_cell_length_b                   10.7217(12)
_cell_length_c                   10.8522(13)
_cell_angle_alpha                66.536(3)
_cell_angle_beta                 86.529(4)
_cell_angle_gamma                76.874(3)
_cell_volume                     1036.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6895
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      27.20

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15704
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         27.52
_reflns_number_total             4707
_reflns_number_gt                3416
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0707P)²+0.7983P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4707
_refine_ls_number_parameters     289
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.1765
_refine_ls_wR_factor_gt          0.1600
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.116
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3661(3) 0.4359(3) 0.4129(3) 0.0498(7) Uani 1 1 d . . .
H1 H 0.3153 0.5115 0.3425 0.060 Uiso 1 1 calc R . .
C2 C 0.3527(3) 0.4289(3) 0.5423(3) 0.0592(8) Uani 1 1 d . . .
H2 H 0.2916 0.4995 0.5591 0.071 Uiso 1 1 calc R . .
C3 C 0.4287(3) 0.3185(3) 0.6470(3) 0.0562(8) Uani 1 1 d . . .
H3 H 0.4212 0.3167 0.7335 0.067 Uiso 1 1 calc R . .
C4 C 0.5159(3) 0.2108(3) 0.6244(3) 0.0441(6) Uani 1 1 d . . .
H4 H 0.5658 0.1356 0.6957 0.053 Uiso 1 1 calc R . .
C5 C 0.5292(2) 0.2146(2) 0.4949(2) 0.0338(5) Uani 1 1 d . . .
C6 C 0.4558(2) 0.3296(2) 0.3879(2) 0.0356(5) Uani 1 1 d . . .
C7 C 0.4768(2) 0.3393(2) 0.2490(2) 0.0369(5) Uani 1 1 d . . .
C8 C 0.5831(2) 0.2300(2) 0.2258(2) 0.0323(5) Uani 1 1 d . . .
C9 C 0.6494(2) 0.1146(2) 0.3286(2) 0.0312(5) Uani 1 1 d . . .
C10 C 0.6175(2) 0.0954(2) 0.4715(2) 0.0331(5) Uani 1 1 d . . .
C11 C 0.7529(2) 0.0052(2) 0.3055(2) 0.0350(5) Uani 1 1 d . . .
C12 C 0.8730(3) -0.0564(3) 0.3870(3) 0.0416(6) Uani 1 1 d . . .
H12 H 0.8851 -0.0299 0.4566 0.050 Uiso 1 1 calc R . .
C13 C 0.9728(3) -0.1554(3) 0.3650(3) 0.0507(7) Uani 1 1 d . . .
C14 C 0.9572(3) -0.1989(3) 0.2634(4) 0.0608(8) Uani 1 1 d . . .
H14 H 1.0254 -0.2669 0.2498 0.073 Uiso 1 1 calc R . .
C15 C 0.8400(3) -0.1404(3) 0.1836(3) 0.0568(8) Uani 1 1 d . . .
H15 H 0.8286 -0.1699 0.1159 0.068 Uiso 1 1 calc R . .
C16 C 0.7377(3) -0.0380(3) 0.2016(3) 0.0417(6) Uani 1 1 d . . .
C17 C 0.5540(3) 0.1472(3) 0.0508(2) 0.0466(7) Uani 1 1 d . . .
C18 C 0.6089(3) 0.2534(3) 0.0806(2) 0.0410(6) Uani 1 1 d . . .
H18 H 0.5534 0.3456 0.0258 0.049 Uiso 1 1 calc R . .
C19 C 0.7578(3) 0.2523(3) 0.0369(3) 0.0521(7) Uani 1 1 d . . .
C20 C 0.8445(3) 0.3108(4) 0.0966(3) 0.0610(5) Uani 1 1 d U . .
C21 C 0.7926(3) 0.4289(4) 0.1222(3) 0.0612(5) Uani 1 1 d U . .
H21 H 0.7000 0.4726 0.1034 0.073 Uiso 1 1 calc R . .
C22 C 0.8755(4) 0.4826(4) 0.1747(4) 0.0669(5) Uani 1 1 d U . .
H22 H 0.8411 0.5638 0.1889 0.080 Uiso 1 1 calc R . .
C23 C 1.0091(4) 0.4143(4) 0.2057(4) 0.0738(6) Uani 1 1 d U . .
C24 C 1.0653(4) 0.2974(4) 0.1854(4) 0.0760(6) Uani 1 1 d U . .
H24 H 1.1569 0.2528 0.2095 0.091 Uiso 1 1 calc R . .
C25 C 0.9821(4) 0.2449(4) 0.1270(4) 0.0705(5) Uani 1 1 d U . .
H25 H 1.0189 0.1664 0.1089 0.085 Uiso 1 1 calc R . .
Cl1 Cl 1.12299(9) -0.22536(10) 0.46535(12) 0.0851(4) Uani 1 1 d . . .
F1 F 1.0902(3) 0.4650(4) 0.2612(4) 0.1486(13) Uani 1 1 d . . .
N1 N 0.6196(3) 0.0132(2) 0.1165(2) 0.0476(6) Uani 1 1 d . . .
H1A H 0.5852 -0.0482 0.1052 0.057 Uiso 1 1 calc R . .
O1 O 0.4131(2) 0.4374(2) 0.15358(19) 0.0602(6) Uani 1 1 d . . .
O2 O 0.6594(2) -0.01526(18) 0.56438(17) 0.0456(5) Uani 1 1 d . . .
O3 O 0.4547(3) 0.1811(2) -0.0257(2) 0.0655(6) Uani 1 1 d . . .
O4 O 0.8002(3) 0.2061(3) -0.0464(3) 0.0859(9) Uani 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
C1 C2 1.376(4) . ?
C1 C6 1.388(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.376(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(3) . ?
C5 C10 1.481(3) . ?
C6 C7 1.474(3) . ?
C7 O1 1.221(3) . ?
C7 C8 1.484(3) . ?
C8 C9 1.354(3) . ?
C8 C18 1.509(3) . ?
C9 C11 1.469(3) . ?
C9 C10 1.505(3) . ?
C10 O2 1.213(3) . ?
C11 C12 1.400(3) . ?
C11 C16 1.406(3) . ?
C12 C13 1.366(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.386(4) . ?
C13 Cl1 1.742(3) . ?
C14 C15 1.367(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(4) . ?
C15 H15 0.9300 . ?
C16 N1 1.407(3) . ?
C17 O3 1.224(3) . ?
C17 N1 1.347(4) . ?
C17 C18 1.517(4) . ?
C18 C19 1.531(4) . ?
C18 H18 0.9800 . ?
C19 O4 1.207(3) . ?
C19 C20 1.482(4) . ?
C20 C21 1.384(5) . ?
C20 C25 1.386(5) . ?
C21 C22 1.369(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.357(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.349(5) . ?
C23 F1 1.353(4) . ?
C24 C25 1.403(5) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
N1 H1A 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.7(3) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C1 C2 C3 120.7(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 119.6(2) . . ?
C4 C5 C10 119.9(2) . . ?
C6 C5 C10 120.4(2) . . ?
C1 C6 C5 119.7(2) . . ?
C1 C6 C7 120.3(2) . . ?
C5 C6 C7 120.0(2) . . ?
O1 C7 C6 121.6(2) . . ?
O1 C7 C8 119.9(2) . . ?
C6 C7 C8 118.4(2) . . ?
C9 C8 C7 121.9(2) . . ?
C9 C8 C18 122.3(2) . . ?
C7 C8 C18 115.8(2) . . ?
C8 C9 C11 121.9(2) . . ?
C8 C9 C10 120.0(2) . . ?
C11 C9 C10 118.15(19) . . ?
O2 C10 C5 120.9(2) . . ?
O2 C10 C9 121.2(2) . . ?
C5 C10 C9 117.88(19) . . ?
C12 C11 C16 118.2(2) . . ?
C12 C11 C9 119.3(2) . . ?
C16 C11 C9 122.4(2) . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 121.2(3) . . ?
C12 C13 Cl1 119.0(2) . . ?
C14 C13 Cl1 119.8(2) . . ?
C15 C14 C13 119.0(3) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 121.4(3) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C11 119.7(3) . . ?
C15 C16 N1 117.1(2) . . ?
C11 C16 N1 123.2(2) . . ?
O3 C17 N1 122.4(2) . . ?
O3 C17 C18 122.1(3) . . ?
N1 C17 C18 115.5(2) . . ?
C8 C18 C17 108.2(2) . . ?
C8 C18 C19 116.3(2) . . ?
C17 C18 C19 110.9(2) . . ?
C8 C18 H18 107.0 . . ?
C17 C18 H18 107.0 . . ?
C19 C18 H18 107.0 . . ?
O4 C19 C20 122.1(3) . . ?
O4 C19 C18 119.1(3) . . ?
C20 C19 C18 118.8(2) . . ?
C21 C20 C25 119.1(3) . . ?
C21 C20 C19 122.1(3) . . ?
C25 C20 C19 118.7(3) . . ?
C22 C21 C20 121.0(3) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C23 C22 C21 118.4(4) . . ?
C23 C22 H22 120.8 . . ?
C21 C22 H22 120.8 . . ?
C24 C23 F1 118.1(4) . . ?
C24 C23 C22 123.4(4) . . ?
F1 C23 C22 118.5(4) . . ?
C23 C24 C25 118.4(4) . . ?
C23 C24 H24 120.8 . . ?
C25 C24 H24 120.8 . . ?
C20 C25 C24 119.6(4) . . ?
C20 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C17 N1 C16 127.6(2) . . ?
C17 N1 H1A 116.2 . . ?
C16 N1 H1A 116.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O3 0.86 2.05 2.878(3) 161.1 2_655

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.737
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_2c
_audit_block_doi                 10.5517/cc1kkpzs
_database_code_depnum_ccdc_archive 'CCDC 1446986'
_audit_update_record             
;
2016-01-13 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H12 F N O5'
_chemical_formula_sum            'C20 H12 F N O5'
_chemical_formula_weight         365.31

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.727(6)
_cell_length_b                   12.810(6)
_cell_length_c                   12.935(6)
_cell_angle_alpha                103.837(13)
_cell_angle_beta                 115.433(12)
_cell_angle_gamma                91.903(14)
_cell_volume                     1683.3(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1882
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      22.48

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20671
_diffrn_reflns_av_R_equivalents  0.2849
_diffrn_reflns_av_sigmaI/netI    0.3311
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5833
_reflns_number_gt                1863
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0991P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5833
_refine_ls_number_parameters     490
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2987
_refine_ls_R_factor_gt           0.0904
_refine_ls_wR_factor_ref         0.2320
_refine_ls_wR_factor_gt          0.1861
_refine_ls_goodness_of_fit_ref   0.848
_refine_ls_restrained_S_all      0.848
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5082(6) 0.8015(5) 0.4287(5) 0.0369(16) Uani 1 1 d . . .
C2 C 0.4612(7) 0.8456(5) 0.5080(5) 0.0523(19) Uani 1 1 d . . .
H2 H 0.4953 0.8318 0.5821 0.063 Uiso 1 1 calc R . .
C3 C 0.3673(7) 0.9082(5) 0.4822(6) 0.0529(19) Uani 1 1 d . . .
H3 H 0.3352 0.9360 0.5359 0.063 Uiso 1 1 calc R . .
C4 C 0.3217(7) 0.9286(5) 0.3730(6) 0.0483(18) Uani 1 1 d . . .
C5 C 0.3635(6) 0.8881(5) 0.2909(5) 0.0437(17) Uani 1 1 d . . .
H5 H 0.3275 0.9030 0.2174 0.052 Uiso 1 1 calc R . .
C6 C 0.4599(6) 0.8247(5) 0.3168(5) 0.0376(16) Uani 1 1 d . . .
C7 C 0.6256(7) 0.6493(5) 0.4068(5) 0.0397(17) Uani 1 1 d . . .
C8 C 0.5244(6) 0.6025(5) 0.2780(5) 0.0362(16) Uani 1 1 d . . .
H8 H 0.5481 0.5338 0.2464 0.043 Uiso 1 1 calc R . .
C9 C 0.3930(8) 0.5771(5) 0.2619(6) 0.0490(19) Uani 1 1 d . . .
C10 C 0.2749(8) 0.5218(8) 0.3552(8) 0.120(4) Uani 1 1 d . . .
H10A H 0.2160 0.5662 0.3158 0.179 Uiso 1 1 calc R . .
H10B H 0.2848 0.5340 0.4350 0.179 Uiso 1 1 calc R . .
H10C H 0.2424 0.4465 0.3122 0.179 Uiso 1 1 calc R . .
C11 C 0.5366(6) 0.8590(5) 0.1681(5) 0.0462(18) Uani 1 1 d . . .
C12 C 0.5086(6) 0.7821(5) 0.2292(5) 0.0387(17) Uani 1 1 d . . .
C13 C 0.5384(6) 0.6811(5) 0.2095(5) 0.0401(17) Uani 1 1 d . . .
C14 C 0.5929(6) 0.6369(6) 0.1255(5) 0.0451(18) Uani 1 1 d . . .
C15 C 0.6123(6) 0.7113(5) 0.0597(5) 0.0450(18) Uani 1 1 d . . .
C16 C 0.6610(7) 0.6720(6) -0.0213(6) 0.063(2) Uani 1 1 d . . .
H16 H 0.6783 0.6010 -0.0347 0.076 Uiso 1 1 calc R . .
C17 C 0.6830(7) 0.7411(7) -0.0815(6) 0.075(2) Uani 1 1 d . . .
H17 H 0.7159 0.7161 -0.1352 0.090 Uiso 1 1 calc R . .
C18 C 0.6573(7) 0.8432(7) -0.0628(6) 0.068(2) Uani 1 1 d . . .
H18 H 0.6712 0.8875 -0.1049 0.082 Uiso 1 1 calc R . .
C19 C 0.6105(7) 0.8841(6) 0.0182(6) 0.064(2) Uani 1 1 d . . .
H19 H 0.5963 0.9560 0.0321 0.077 Uiso 1 1 calc R . .
C20 C 0.5842(6) 0.8160(5) 0.0797(5) 0.0448(17) Uani 1 1 d . . .
C21 C 0.9504(7) 0.2608(5) 0.3410(5) 0.0370(17) Uani 1 1 d . . .
C22 C 0.9180(7) 0.3623(5) 0.3694(5) 0.0528(19) Uani 1 1 d . . .
H22 H 0.9770 0.4240 0.3928 0.063 Uiso 1 1 calc R . .
C23 C 0.8002(9) 0.3734(6) 0.3635(6) 0.061(2) Uani 1 1 d . . .
H23 H 0.7771 0.4416 0.3819 0.074 Uiso 1 1 calc R . .
C24 C 0.7172(8) 0.2796(7) 0.3294(6) 0.0568(19) Uani 1 1 d . . .
C25 C 0.7445(7) 0.1774(5) 0.3030(5) 0.0470(18) Uani 1 1 d . . .
H25 H 0.6848 0.1166 0.2814 0.056 Uiso 1 1 calc R . .
C26 C 0.8637(7) 0.1669(5) 0.3095(5) 0.0368(16) Uani 1 1 d . . .
C27 C 1.1062(8) 0.1955(5) 0.2642(5) 0.0386(17) Uani 1 1 d . . .
C28 C 0.9959(6) 0.1152(5) 0.1591(5) 0.0430(17) Uani 1 1 d . . .
H28 H 1.0298 0.0780 0.1054 0.052 Uiso 1 1 calc R . .
C29 C 0.8853(8) 0.1669(6) 0.0867(5) 0.0455(18) Uani 1 1 d . . .
C30 C 0.8307(8) 0.3288(6) 0.0310(7) 0.104(3) Uani 1 1 d . . .
H30A H 0.7894 0.2867 -0.0512 0.156 Uiso 1 1 calc R . .
H30B H 0.8715 0.3980 0.0377 0.156 Uiso 1 1 calc R . .
H30C H 0.7684 0.3397 0.0605 0.156 Uiso 1 1 calc R . .
C31 C 0.8722(6) -0.0275(5) 0.3337(5) 0.0453(17) Uani 1 1 d . . .
C32 C 0.8975(6) 0.0570(5) 0.2790(5) 0.0423(17) Uani 1 1 d . . .
C33 C 0.9546(6) 0.0291(5) 0.2052(5) 0.0389(16) Uani 1 1 d . . .
C34 C 0.9818(6) -0.0812(5) 0.1693(6) 0.0446(17) Uani 1 1 d . . .
C35 C 0.9581(6) -0.1641(5) 0.2234(5) 0.0470(18) Uani 1 1 d . . .
C36 C 0.9878(7) -0.2673(5) 0.1972(6) 0.064(2) Uani 1 1 d . . .
H36 H 1.0230 -0.2856 0.1444 0.076 Uiso 1 1 calc R . .
C37 C 0.9657(8) -0.3434(6) 0.2484(7) 0.076(2) Uani 1 1 d . . .
H37 H 0.9843 -0.4133 0.2292 0.091 Uiso 1 1 calc R . .
C38 C 0.9154(7) -0.3148(6) 0.3292(7) 0.068(2) Uani 1 1 d . . .
H38 H 0.9011 -0.3662 0.3641 0.081 Uiso 1 1 calc R . .
C39 C 0.8868(7) -0.2136(6) 0.3579(6) 0.061(2) Uani 1 1 d . . .
H39 H 0.8534 -0.1961 0.4123 0.073 Uiso 1 1 calc R . .
C40 C 0.9075(6) -0.1351(5) 0.3057(5) 0.0437(18) Uani 1 1 d . . .
F1 F 0.2291(4) 0.9950(3) 0.3482(3) 0.0681(12) Uani 1 1 d . . .
F2 F 0.5970(4) 0.2908(3) 0.3223(4) 0.0822(13) Uani 1 1 d . . .
N1 N 0.6108(5) 0.7423(4) 0.4670(4) 0.0417(14) Uani 1 1 d . . .
H1 H 0.6708 0.7701 0.5382 0.050 Uiso 1 1 calc R . .
N2 N 1.0750(5) 0.2555(4) 0.3486(4) 0.0427(14) Uani 1 1 d . . .
H2A H 1.1376 0.2944 0.4136 0.051 Uiso 1 1 calc R . .
O1 O 0.7201(4) 0.6035(3) 0.4490(3) 0.0505(12) Uani 1 1 d . . .
O2 O 0.2946(5) 0.5781(4) 0.1808(4) 0.0655(15) Uani 1 1 d . . .
O3 O 0.3955(5) 0.5498(4) 0.3590(4) 0.0749(16) Uani 1 1 d . . .
O4 O 0.5232(5) 0.9533(4) 0.1935(4) 0.0639(14) Uani 1 1 d . . .
O5 O 0.6217(5) 0.5454(4) 0.1149(4) 0.0651(14) Uani 1 1 d . . .
O6 O 1.2152(5) 0.2040(3) 0.2774(4) 0.0518(13) Uani 1 1 d . . .
O7 O 0.7785(5) 0.1222(4) 0.0240(4) 0.0682(15) Uani 1 1 d . . .
O8 O 0.9261(4) 0.2711(4) 0.1004(3) 0.0613(14) Uani 1 1 d . . .
O9 O 0.8292(5) -0.0017(4) 0.4054(4) 0.0768(16) Uani 1 1 d . . .
O10 O 1.0196(5) -0.1047(3) 0.0932(4) 0.0654(15) Uani 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
C1 C2 1.381(8) . ?
C1 N1 1.413(7) . ?
C1 C6 1.420(7) . ?
C2 C3 1.356(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.355(8) . ?
C4 F1 1.378(6) . ?
C5 C6 1.385(8) . ?
C5 H5 0.9300 . ?
C6 C12 1.479(8) . ?
C7 O1 1.245(7) . ?
C7 N1 1.319(7) . ?
C7 C8 1.523(8) . ?
C8 C9 1.478(9) . ?
C8 C13 1.539(8) . ?
C8 H8 0.9800 . ?
C9 O2 1.183(7) . ?
C9 O3 1.371(7) . ?
C10 O3 1.425(8) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 O4 1.209(6) . ?
C11 C20 1.479(8) . ?
C11 C12 1.508(8) . ?
C12 C13 1.345(8) . ?
C13 C14 1.495(8) . ?
C14 O5 1.224(7) . ?
C14 C15 1.492(8) . ?
C15 C20 1.383(8) . ?
C15 C16 1.399(8) . ?
C16 C17 1.395(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.341(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.387(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.419(8) . ?
C19 H19 0.9300 . ?
C21 C22 1.376(8) . ?
C21 C26 1.405(8) . ?
C21 N2 1.427(7) . ?
C22 C23 1.365(9) . ?
C22 H22 0.9300 . ?
C23 C24 1.373(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.356(9) . ?
C24 F2 1.387(8) . ?
C25 C26 1.378(8) . ?
C25 H25 0.9300 . ?
C26 C32 1.484(8) . ?
C27 O6 1.212(7) . ?
C27 N2 1.371(7) . ?
C27 C28 1.520(8) . ?
C28 C29 1.520(8) . ?
C28 C33 1.527(8) . ?
C28 H28 0.9800 . ?
C29 O7 1.188(7) . ?
C29 O8 1.346(7) . ?
C30 O8 1.454(7) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 O9 1.220(7) . ?
C31 C40 1.460(8) . ?
C31 C32 1.511(8) . ?
C32 C33 1.375(8) . ?
C33 C34 1.468(8) . ?
C34 O10 1.223(7) . ?
C34 C35 1.483(8) . ?
C35 C36 1.379(8) . ?
C35 C40 1.412(8) . ?
C36 C37 1.378(9) . ?
C36 H36 0.9300 . ?
C37 C38 1.390(10) . ?
C37 H37 0.9300 . ?
C38 C39 1.356(9) . ?
C38 H38 0.9300 . ?
C39 C40 1.405(8) . ?
C39 H39 0.9300 . ?
N1 H1 0.8600 . ?
N2 H2A 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 117.9(5) . . ?
C2 C1 C6 119.3(6) . . ?
N1 C1 C6 122.6(5) . . ?
C3 C2 C1 122.6(6) . . ?
C3 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
C2 C3 C4 116.8(6) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
C5 C4 C3 123.8(6) . . ?
C5 C4 F1 119.4(6) . . ?
C3 C4 F1 116.8(6) . . ?
C4 C5 C6 119.8(6) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 117.7(6) . . ?
C5 C6 C12 120.4(5) . . ?
C1 C6 C12 121.9(6) . . ?
O1 C7 N1 122.8(6) . . ?
O1 C7 C8 120.4(5) . . ?
N1 C7 C8 116.7(6) . . ?
C9 C8 C7 115.2(5) . . ?
C9 C8 C13 114.2(5) . . ?
C7 C8 C13 106.4(5) . . ?
C9 C8 H8 106.8 . . ?
C7 C8 H8 106.8 . . ?
C13 C8 H8 106.8 . . ?
O2 C9 O3 120.6(7) . . ?
O2 C9 C8 129.1(6) . . ?
O3 C9 C8 110.3(6) . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C11 C20 121.5(6) . . ?
O4 C11 C12 120.4(6) . . ?
C20 C11 C12 118.0(6) . . ?
C13 C12 C6 122.7(6) . . ?
C13 C12 C11 119.0(6) . . ?
C6 C12 C11 118.1(5) . . ?
C12 C13 C14 124.2(6) . . ?
C12 C13 C8 121.7(6) . . ?
C14 C13 C8 114.1(5) . . ?
O5 C14 C15 123.0(6) . . ?
O5 C14 C13 120.7(6) . . ?
C15 C14 C13 116.3(6) . . ?
C20 C15 C16 121.5(6) . . ?
C20 C15 C14 120.7(6) . . ?
C16 C15 C14 117.8(6) . . ?
C17 C16 C15 118.8(7) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C18 C17 C16 120.7(8) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 121.4(7) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C20 119.9(7) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C15 C20 C19 117.7(6) . . ?
C15 C20 C11 121.6(6) . . ?
C19 C20 C11 120.6(6) . . ?
C22 C21 C26 120.2(7) . . ?
C22 C21 N2 117.6(6) . . ?
C26 C21 N2 122.2(6) . . ?
C23 C22 C21 120.7(7) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 117.2(7) . . ?
C22 C23 H23 121.4 . . ?
C24 C23 H23 121.4 . . ?
C25 C24 C23 124.8(7) . . ?
C25 C24 F2 118.0(7) . . ?
C23 C24 F2 117.2(7) . . ?
C24 C25 C26 117.6(7) . . ?
C24 C25 H25 121.2 . . ?
C26 C25 H25 121.2 . . ?
C25 C26 C21 119.4(6) . . ?
C25 C26 C32 119.8(6) . . ?
C21 C26 C32 120.8(6) . . ?
O6 C27 N2 121.2(6) . . ?
O6 C27 C28 124.0(6) . . ?
N2 C27 C28 114.7(6) . . ?
C27 C28 C29 114.6(5) . . ?
C27 C28 C33 108.2(5) . . ?
C29 C28 C33 112.9(5) . . ?
C27 C28 H28 106.9 . . ?
C29 C28 H28 106.9 . . ?
C33 C28 H28 106.9 . . ?
O7 C29 O8 124.2(6) . . ?
O7 C29 C28 125.6(6) . . ?
O8 C29 C28 110.2(6) . . ?
O8 C30 H30A 109.5 . . ?
O8 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O8 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O9 C31 C40 121.7(6) . . ?
O9 C31 C32 118.8(6) . . ?
C40 C31 C32 119.4(6) . . ?
C33 C32 C26 122.7(6) . . ?
C33 C32 C31 118.1(6) . . ?
C26 C32 C31 119.2(6) . . ?
C32 C33 C34 123.0(6) . . ?
C32 C33 C28 120.0(5) . . ?
C34 C33 C28 117.0(6) . . ?
O10 C34 C33 120.3(6) . . ?
O10 C34 C35 120.8(6) . . ?
C33 C34 C35 118.9(6) . . ?
C36 C35 C40 119.8(6) . . ?
C36 C35 C34 121.2(6) . . ?
C40 C35 C34 119.0(6) . . ?
C37 C36 C35 120.6(7) . . ?
C37 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C36 C37 C38 119.5(7) . . ?
C36 C37 H37 120.3 . . ?
C38 C37 H37 120.3 . . ?
C39 C38 C37 121.3(7) . . ?
C39 C38 H38 119.4 . . ?
C37 C38 H38 119.4 . . ?
C38 C39 C40 120.1(7) . . ?
C38 C39 H39 119.9 . . ?
C40 C39 H39 119.9 . . ?
C39 C40 C35 118.7(6) . . ?
C39 C40 C31 119.9(6) . . ?
C35 C40 C31 121.4(6) . . ?
C7 N1 C1 127.8(5) . . ?
C7 N1 H1 116.1 . . ?
C1 N1 H1 116.1 . . ?
C27 N2 C21 127.4(5) . . ?
C27 N2 H2A 116.3 . . ?
C21 N2 H2A 116.3 . . ?
C9 O3 C10 116.5(6) . . ?
C29 O8 C30 115.9(6) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O6 0.86 2.11 2.931(6) 160.2 2_766
N2 H2A O1 0.86 1.96 2.817(7) 172.9 2_766

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.093
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2h
_audit_block_doi                 10.5517/cc1kkq0v
_database_code_depnum_ccdc_archive 'CCDC 1446987'
_audit_update_record             
;
2016-01-13 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H14 Cl N O5'
_chemical_formula_sum            'C21 H14 Cl N O5'
_chemical_formula_weight         395.78

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'
Cl Cl 0.1484 0.1585 '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
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'


loop_
_symmetry_equiv_pos_as_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                   22.142(2)
_cell_length_b                   15.2704(16)
_cell_length_c                   12.2599(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.973(4)
_cell_angle_gamma                90.00
_cell_volume                     3726.6(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9920
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      27.40

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1632
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.927
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25559
_diffrn_reflns_av_R_equivalents  0.0902
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         27.53
_reflns_number_total             4281
_reflns_number_gt                3167
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0881P)²+1.1336P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4281
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1636
_refine_ls_wR_factor_gt          0.1484
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.18395(8) -0.04278(12) 0.60753(14) 0.0392(4) Uani 1 1 d . . .
C2 C 0.21050(10) -0.12675(13) 0.62126(17) 0.0489(5) Uani 1 1 d . . .
H2 H 0.2448 -0.1435 0.6955 0.059 Uiso 1 1 calc R . .
C3 C 0.18681(11) -0.18533(13) 0.52657(19) 0.0542(5) Uani 1 1 d . . .
H3 H 0.2039 -0.2419 0.5369 0.065 Uiso 1 1 calc R . .
C4 C 0.13729(10) -0.15892(13) 0.41615(18) 0.0511(5) Uani 1 1 d . . .
C5 C 0.10977(9) -0.07708(12) 0.39955(16) 0.0440(4) Uani 1 1 d . . .
H5 H 0.0763 -0.0610 0.3241 0.053 Uiso 1 1 calc R . .
C6 C 0.13193(8) -0.01715(11) 0.49624(15) 0.0372(4) Uani 1 1 d . . .
C7 C 0.10100(8) 0.07008(11) 0.47886(14) 0.0361(4) Uani 1 1 d . . .
C8 C 0.13812(8) 0.14290(11) 0.52393(14) 0.0386(4) Uani 1 1 d . . .
C9 C 0.21352(8) 0.13892(12) 0.59458(15) 0.0405(4) Uani 1 1 d . . .
H9 H 0.2298 0.1994 0.6109 0.049 Uiso 1 1 calc R . .
C10 C 0.23085(8) 0.09582(12) 0.71688(15) 0.0432(4) Uani 1 1 d . . .
C11 C 0.24754(8) 0.09576(11) 0.52459(15) 0.0395(4) Uani 1 1 d . . .
C12 C 0.34031(10) 0.00840(15) 0.5447(2) 0.0587(5) Uani 1 1 d . . .
H12A H 0.3506 0.0454 0.4907 0.070 Uiso 1 1 calc R . .
H12B H 0.3129 -0.0402 0.4982 0.070 Uiso 1 1 calc R . .
C13 C 0.40333(13) -0.0247(2) 0.6447(3) 0.0900(9) Uani 1 1 d . . .
H13A H 0.4305 0.0239 0.6889 0.135 Uiso 1 1 calc R . .
H13B H 0.4276 -0.0590 0.6115 0.135 Uiso 1 1 calc R . .
H13C H 0.3926 -0.0603 0.6984 0.135 Uiso 1 1 calc R . .
C14 C 0.02608(8) 0.07668(13) 0.40963(15) 0.0426(4) Uani 1 1 d . . .
C15 C -0.00494(9) 0.16453(14) 0.39071(16) 0.0471(5) Uani 1 1 d . . .
C16 C -0.07414(10) 0.17265(17) 0.3215(2) 0.0640(6) Uani 1 1 d . . .
H16 H -0.1000 0.1236 0.2852 0.077 Uiso 1 1 calc R . .
C17 C -0.10385(13) 0.2532(2) 0.3072(3) 0.0860(9) Uani 1 1 d . . .
H17 H -0.1500 0.2586 0.2607 0.103 Uiso 1 1 calc R . .
C18 C -0.06633(15) 0.3258(2) 0.3606(3) 0.0957(10) Uani 1 1 d . . .
H18 H -0.0874 0.3799 0.3511 0.115 Uiso 1 1 calc R . .
C19 C 0.00284(13) 0.31993(17) 0.4288(3) 0.0804(8) Uani 1 1 d . . .
H19 H 0.0281 0.3695 0.4647 0.097 Uiso 1 1 calc R . .
C20 C 0.03360(10) 0.23837(14) 0.4425(2) 0.0543(5) Uani 1 1 d . . .
C21 C 0.10765(10) 0.23065(12) 0.51106(19) 0.0504(5) Uani 1 1 d . . .
Cl1 Cl 0.10842(4) -0.23128(4) 0.29385(6) 0.0844(3) Uani 1 1 d . . .
N1 N 0.20930(7) 0.01214(10) 0.71110(12) 0.0442(4) Uani 1 1 d . . .
H1 H 0.2112 -0.0099 0.7771 0.053 Uiso 1 1 calc R . .
O1 O 0.26064(7) 0.13417(10) 0.81235(12) 0.0611(4) Uani 1 1 d . . .
O2 O 0.22582(6) 0.09737(10) 0.41601(11) 0.0514(3) Uani 1 1 d . . .
O3 O 0.30466(6) 0.05836(9) 0.59938(11) 0.0477(3) Uani 1 1 d . . .
O4 O 0.14292(8) 0.29461(10) 0.55430(19) 0.0813(5) Uani 1 1 d . . .
O5 O -0.00850(6) 0.01157(10) 0.37187(13) 0.0601(4) Uani 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
C1 C2 1.390(3) . ?
C1 C6 1.402(2) . ?
C1 N1 1.416(2) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(3) . ?
C4 Cl1 1.743(2) . ?
C5 C6 1.405(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.470(2) . ?
C7 C8 1.349(2) . ?
C7 C14 1.500(2) . ?
C8 C21 1.477(3) . ?
C8 C9 1.508(2) . ?
C9 C11 1.518(3) . ?
C9 C10 1.525(2) . ?
C9 H9 0.9800 . ?
C10 O1 1.213(2) . ?
C10 N1 1.355(2) . ?
C11 O2 1.201(2) . ?
C11 O3 1.323(2) . ?
C12 O3 1.455(2) . ?
C12 C13 1.486(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O5 1.216(2) . ?
C14 C15 1.478(3) . ?
C15 C20 1.389(3) . ?
C15 C16 1.394(3) . ?
C16 C17 1.369(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.369(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.390(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.394(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.484(3) . ?
C21 O4 1.217(2) . ?
N1 H1 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.94(16) . . ?
C2 C1 N1 117.21(15) . . ?
C6 C1 N1 122.78(16) . . ?
C3 C2 C1 120.89(17) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 118.99(17) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 121.69(18) . . ?
C5 C4 Cl1 118.70(15) . . ?
C3 C4 Cl1 119.61(15) . . ?
C4 C5 C6 120.13(17) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.29(16) . . ?
C1 C6 C7 121.74(15) . . ?
C5 C6 C7 119.97(15) . . ?
C8 C7 C6 121.73(14) . . ?
C8 C7 C14 120.06(16) . . ?
C6 C7 C14 118.21(14) . . ?
C7 C8 C21 122.42(15) . . ?
C7 C8 C9 121.65(15) . . ?
C21 C8 C9 115.89(15) . . ?
C8 C9 C11 113.04(13) . . ?
C8 C9 C10 108.71(14) . . ?
C11 C9 C10 113.26(14) . . ?
C8 C9 H9 107.2 . . ?
C11 C9 H9 107.2 . . ?
C10 C9 H9 107.2 . . ?
O1 C10 N1 122.41(17) . . ?
O1 C10 C9 122.45(17) . . ?
N1 C10 C9 115.12(14) . . ?
O2 C11 O3 125.03(17) . . ?
O2 C11 C9 124.09(15) . . ?
O3 C11 C9 110.86(14) . . ?
O3 C12 C13 107.53(19) . . ?
O3 C12 H12A 110.2 . . ?
C13 C12 H12A 110.2 . . ?
O3 C12 H12B 110.2 . . ?
C13 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 C15 120.69(16) . . ?
O5 C14 C7 121.10(17) . . ?
C15 C14 C7 118.20(16) . . ?
C20 C15 C16 119.8(2) . . ?
C20 C15 C14 120.99(16) . . ?
C16 C15 C14 119.17(19) . . ?
C17 C16 C15 119.7(2) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C16 120.6(2) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 120.9(2) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C19 C20 118.8(3) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C15 C20 C19 120.0(2) . . ?
C15 C20 C21 119.98(17) . . ?
C19 C20 C21 120.0(2) . . ?
O4 C21 C8 120.36(18) . . ?
O4 C21 C20 121.45(18) . . ?
C8 C21 C20 118.18(17) . . ?
C10 N1 C1 126.69(14) . . ?
C10 N1 H1 116.7 . . ?
C1 N1 H1 116.7 . . ?
C11 O3 C12 117.00(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.86 2.08 2.905(2) 161.7 6_556

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_3b
_audit_block_doi                 10.5517/cc1kkq1w
_database_code_depnum_ccdc_archive 'CCDC 1446988'
_audit_update_record             
;
2016-01-13 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H21 N3 O5'
_chemical_formula_weight         503.50

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.8577(7)
_cell_length_b                   14.7678(8)
_cell_length_c                   16.2529(8)
_cell_angle_alpha                90
_cell_angle_beta                 112.1542(18)
_cell_angle_gamma                90
_cell_volume                     2858.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4375
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      23.04

_exptl_crystal_description       block
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6643
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            20467
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.197
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_full        25.020
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5048
_reflns_number_gt                3174
_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.
;

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 0.000 0.000 0.500 329 73 ' '
2 0.000 0.500 0.000 329 73 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0804P)²+1.6407P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5048
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0659
_refine_ls_wR_factor_ref         0.1825
_refine_ls_wR_factor_gt          0.1613
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
C1 C 0.3685(3) 0.5190(2) 0.08349(19) 0.0398(7) Uani 1 1 d . . . . .
C2 C 0.4039(3) 0.4314(2) 0.1021(2) 0.0510(9) Uani 1 1 d . . . . .
H2 H 0.4232 0.4078 0.1590 0.061 Uiso 1 1 calc R U . . .
C3 C 0.4103(3) 0.3789(2) 0.0335(2) 0.0573(9) Uani 1 1 d . . . . .
H3 H 0.4350 0.3193 0.0448 0.069 Uiso 1 1 calc R U . . .
C4 C 0.3806(3) 0.4133(2) -0.0508(2) 0.0553(9) Uani 1 1 d . . . . .
H4 H 0.3855 0.3767 -0.0958 0.066 Uiso 1 1 calc R U . . .
C5 C 0.3433(3) 0.5023(2) -0.0698(2) 0.0486(8) Uani 1 1 d . . . . .
H5 H 0.3222 0.5255 -0.1269 0.058 Uiso 1 1 calc R U . . .
C6 C 0.3386(2) 0.5545(2) -0.00151(19) 0.0389(7) Uani 1 1 d . . . . .
C7 C 0.3228(2) 0.67251(19) 0.09024(17) 0.0352(7) Uani 1 1 d . . . . .
C8 C 0.2880(2) 0.7585(2) 0.12340(17) 0.0359(7) Uani 1 1 d . . . . .
C9 C 0.2927(2) 0.84325(19) 0.06723(18) 0.0358(7) Uani 1 1 d . . . . .
H9 H 0.2282 0.8371 0.0109 0.043 Uiso 1 1 calc R U . . .
C10 C 0.4969(3) 0.8290(2) 0.0990(2) 0.0447(8) Uani 1 1 d . . . . .
H10 H 0.5078 0.8062 0.1551 0.054 Uiso 1 1 calc R U . . .
C11 C 0.5878(3) 0.8412(2) 0.0740(2) 0.0540(9) Uani 1 1 d . . . . .
H11 H 0.6602 0.8288 0.1139 0.065 Uiso 1 1 calc R U . . .
C12 C 0.5701(3) 0.8717(2) -0.0099(2) 0.0564(9) Uani 1 1 d . . . . .
H12 H 0.6305 0.8796 -0.0275 0.068 Uiso 1 1 calc R U . . .
C13 C 0.4630(3) 0.8906(2) -0.0677(2) 0.0521(9) Uani 1 1 d . . . . .
H13 H 0.4498 0.9106 -0.1250 0.063 Uiso 1 1 calc R U . . .
C14 C 0.3762(3) 0.8794(2) -0.03996(19) 0.0451(8) Uani 1 1 d . . . . .
H14 H 0.3035 0.8924 -0.0788 0.054 Uiso 1 1 calc R U . . .
C15 C 0.2755(2) 0.9332(2) 0.10631(18) 0.0377(7) Uani 1 1 d . . . . .
C16 C 0.3619(3) 0.9830(2) 0.16597(19) 0.0413(8) Uani 1 1 d . . . . .
H16 H 0.4350 0.9609 0.1845 0.050 Uiso 1 1 calc R U . . .
C17 C 0.3422(3) 1.0652(2) 0.1989(2) 0.0480(8) Uani 1 1 d . . . . .
H17 H 0.4010 1.0991 0.2381 0.058 Uiso 1 1 calc R U . . .
C18 C 0.2344(3) 1.0944(2) 0.1720(2) 0.0482(8) Uani 1 1 d . . . . .
C19 C 0.1470(3) 1.0473(3) 0.1140(3) 0.0671(11) Uani 1 1 d . . . . .
H19 H 0.0740 1.0689 0.0971 0.081 Uiso 1 1 calc R U . . .
C20 C 0.1682(3) 0.9671(3) 0.0806(3) 0.0651(11) Uani 1 1 d . . . . .
H20 H 0.1089 0.9351 0.0397 0.078 Uiso 1 1 calc R U . . .
C21 C 0.3556(3) 0.77291(19) 0.22520(19) 0.0405(7) Uani 1 1 d . . . . .
C22 C 0.1707(3) 0.7647(2) 0.2058(2) 0.0502(9) Uani 1 1 d . . . . .
C23 C 0.1687(3) 0.7525(2) 0.1209(2) 0.0426(8) Uani 1 1 d . . . . .
C24 C 0.0691(3) 0.7345(2) 0.0517(2) 0.0545(9) Uani 1 1 d . . . . .
H24 H 0.0681 0.7253 -0.0052 0.065 Uiso 1 1 calc R U . . .
C25 C -0.0303(3) 0.7300(3) 0.0670(3) 0.0727(12) Uani 1 1 d . . . . .
C26 C -0.0251(4) 0.7438(4) 0.1526(3) 0.0885(14) Uani 1 1 d . . . . .
H26 H -0.0914 0.7412 0.1631 0.106 Uiso 1 1 calc R U . . .
C27 C 0.0743(4) 0.7614(3) 0.2234(3) 0.0787(13) Uani 1 1 d . . . . .
H27 H 0.0758 0.7707 0.2805 0.094 Uiso 1 1 calc R U . . .
C28 C -0.1409(3) 0.7080(4) -0.0058(3) 0.1071(18) Uani 1 1 d . . . . .
H28A H -0.1727 0.6554 0.0105 0.161 Uiso 1 1 calc R U . . .
H28B H -0.1294 0.6963 -0.0598 0.161 Uiso 1 1 calc R U . . .
H28C H -0.1912 0.7583 -0.0144 0.161 Uiso 1 1 calc R U . . .
C29 C 0.3051(2) 0.6518(2) 0.00070(18) 0.0370(7) Uani 1 1 d . . . . .
C30 C 0.3563(2) 0.5928(2) 0.14217(19) 0.0388(7) Uani 1 1 d . . . . .
N1 N 0.2801(2) 0.78021(18) 0.26476(16) 0.0492(7) Uani 1 1 d . . . . .
H1A H 0.3010 0.7863 0.3256 0.059 Uiso 1 1 d R U . . .
N2 N 0.3932(2) 0.84997(15) 0.04230(15) 0.0365(6) Uani 1 1 d . . . . .
N3 N 0.2101(3) 1.1815(2) 0.2064(2) 0.0663(9) Uani 1 1 d . . . . .
O1 O 0.3733(2) 0.58205(14) 0.22250(13) 0.0550(6) Uani 1 1 d . . . . .
O2 O 0.26913(19) 0.70180(14) -0.06676(13) 0.0492(6) Uani 1 1 d . . . . .
O3 O 0.45711(19) 0.77948(15) 0.26204(13) 0.0496(6) Uani 1 1 d . . . . .
O4 O 0.1128(3) 1.2047(2) 0.1848(2) 0.0993(11) Uani 1 1 d . . . . .
O5 O 0.2887(3) 1.2264(2) 0.2529(2) 0.1024(11) Uani 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
C1 C2 1.367(4) . ?
C1 C6 1.390(4) . ?
C1 C30 1.494(4) . ?
C2 C3 1.385(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(4) . ?
C5 H5 0.9300 . ?
C6 C29 1.504(4) . ?
C7 C30 1.418(4) . ?
C7 C29 1.419(4) . ?
C7 C8 1.511(4) . ?
C8 C23 1.521(4) . ?
C8 C9 1.564(4) . ?
C8 C21 1.567(4) . ?
C9 N2 1.497(4) . ?
C9 C15 1.524(4) . ?
C9 H9 0.9800 . ?
C10 N2 1.340(4) . ?
C10 C11 1.387(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.363(4) . ?
C13 H13 0.9300 . ?
C14 N2 1.343(4) . ?
C14 H14 0.9300 . ?
C15 C20 1.376(4) . ?
C15 C16 1.379(4) . ?
C16 C17 1.388(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.357(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.356(5) . ?
C18 N3 1.482(4) . ?
C19 C20 1.371(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 O3 1.217(4) . ?
C21 N1 1.355(4) . ?
C22 C27 1.375(5) . ?
C22 C23 1.381(4) . ?
C22 N1 1.391(4) . ?
C23 C24 1.375(4) . ?
C24 C25 1.393(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.383(6) . ?
C25 C28 1.503(6) . ?
C26 C27 1.384(6) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 O2 1.257(3) . ?
C30 O1 1.250(3) . ?
N1 H1A 0.9258 . ?
N3 O5 1.207(4) . ?
N3 O4 1.215(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.4(3) . . ?
C2 C1 C30 130.9(3) . . ?
C6 C1 C30 107.7(3) . . ?
C1 C2 C3 117.9(3) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 118.0(3) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C1 120.8(3) . . ?
C5 C6 C29 131.1(3) . . ?
C1 C6 C29 108.1(2) . . ?
C30 C7 C29 109.0(2) . . ?
C30 C7 C8 123.4(2) . . ?
C29 C7 C8 126.3(3) . . ?
C7 C8 C23 111.9(2) . . ?
C7 C8 C9 112.5(2) . . ?
C23 C8 C9 106.9(2) . . ?
C7 C8 C21 111.7(2) . . ?
C23 C8 C21 100.8(2) . . ?
C9 C8 C21 112.3(2) . . ?
N2 C9 C15 109.3(2) . . ?
N2 C9 C8 116.0(2) . . ?
C15 C9 C8 114.3(2) . . ?
N2 C9 H9 105.4 . . ?
C15 C9 H9 105.4 . . ?
C8 C9 H9 105.4 . . ?
N2 C10 C11 119.8(3) . . ?
N2 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 119.5(3) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 119.0(3) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
N2 C14 C13 121.5(3) . . ?
N2 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C20 C15 C16 118.0(3) . . ?
C20 C15 C9 118.5(3) . . ?
C16 C15 C9 123.5(3) . . ?
C15 C16 C17 121.4(3) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C16 117.8(3) . . ?
C18 C17 H17 121.1 . . ?
C16 C17 H17 121.1 . . ?
C19 C18 C17 122.6(3) . . ?
C19 C18 N3 118.1(3) . . ?
C17 C18 N3 119.3(3) . . ?
C18 C19 C20 118.8(3) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C19 C20 C15 121.3(3) . . ?
C19 C20 H20 119.3 . . ?
C15 C20 H20 119.3 . . ?
O3 C21 N1 125.9(3) . . ?
O3 C21 C8 126.5(3) . . ?
N1 C21 C8 107.5(3) . . ?
C27 C22 C23 121.7(3) . . ?
C27 C22 N1 128.3(3) . . ?
C23 C22 N1 110.0(3) . . ?
C24 C23 C22 120.2(3) . . ?
C24 C23 C8 130.6(3) . . ?
C22 C23 C8 109.1(3) . . ?
C23 C24 C25 119.8(3) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C26 C25 C24 118.3(4) . . ?
C26 C25 C28 119.8(4) . . ?
C24 C25 C28 122.0(4) . . ?
C25 C26 C27 122.9(4) . . ?
C25 C26 H26 118.5 . . ?
C27 C26 H26 118.5 . . ?
C22 C27 C26 117.1(4) . . ?
C22 C27 H27 121.4 . . ?
C26 C27 H27 121.4 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O2 C29 C7 129.2(3) . . ?
O2 C29 C6 123.7(2) . . ?
C7 C29 C6 107.1(2) . . ?
O1 C30 C7 128.4(3) . . ?
O1 C30 C1 123.7(3) . . ?
C7 C30 C1 107.9(2) . . ?
C21 N1 C22 112.3(3) . . ?
C21 N1 H1A 122.9 . . ?
C22 N1 H1A 124.3 . . ?
C10 N2 C14 120.5(3) . . ?
C10 N2 C9 122.3(2) . . ?
C14 N2 C9 117.2(3) . . ?
O5 N3 O4 123.6(4) . . ?
O5 N3 C18 117.8(4) . . ?
O4 N3 C18 118.5(4) . . ?

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
C6 C1 C2 C3 0.6(5) . . . . ?
C30 C1 C2 C3 -177.7(3) . . . . ?
C1 C2 C3 C4 -0.8(5) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
C4 C5 C6 C1 -1.1(5) . . . . ?
C4 C5 C6 C29 178.6(3) . . . . ?
C2 C1 C6 C5 0.4(5) . . . . ?
C30 C1 C6 C5 179.0(3) . . . . ?
C2 C1 C6 C29 -179.4(3) . . . . ?
C30 C1 C6 C29 -0.8(3) . . . . ?
C30 C7 C8 C23 -78.1(3) . . . . ?
C29 C7 C8 C23 87.7(3) . . . . ?
C30 C7 C8 C9 161.5(3) . . . . ?
C29 C7 C8 C9 -32.7(4) . . . . ?
C30 C7 C8 C21 34.1(4) . . . . ?
C29 C7 C8 C21 -160.1(3) . . . . ?
C7 C8 C9 N2 -42.7(3) . . . . ?
C23 C8 C9 N2 -165.9(2) . . . . ?
C21 C8 C9 N2 84.4(3) . . . . ?
C7 C8 C9 C15 -171.3(2) . . . . ?
C23 C8 C9 C15 65.5(3) . . . . ?
C21 C8 C9 C15 -44.2(3) . . . . ?
N2 C10 C11 C12 -2.3(5) . . . . ?
C10 C11 C12 C13 0.6(5) . . . . ?
C11 C12 C13 C14 0.7(5) . . . . ?
C12 C13 C14 N2 -0.4(5) . . . . ?
N2 C9 C15 C20 136.8(3) . . . . ?
C8 C9 C15 C20 -91.3(3) . . . . ?
N2 C9 C15 C16 -42.8(4) . . . . ?
C8 C9 C15 C16 89.0(3) . . . . ?
C20 C15 C16 C17 -0.5(4) . . . . ?
C9 C15 C16 C17 179.2(3) . . . . ?
C15 C16 C17 C18 1.5(4) . . . . ?
C16 C17 C18 C19 -1.0(5) . . . . ?
C16 C17 C18 N3 179.5(3) . . . . ?
C17 C18 C19 C20 -0.4(6) . . . . ?
N3 C18 C19 C20 179.1(3) . . . . ?
C18 C19 C20 C15 1.5(6) . . . . ?
C16 C15 C20 C19 -1.0(5) . . . . ?
C9 C15 C20 C19 179.3(3) . . . . ?
C7 C8 C21 O3 59.0(4) . . . . ?
C23 C8 C21 O3 178.0(3) . . . . ?
C9 C8 C21 O3 -68.5(4) . . . . ?
C7 C8 C21 N1 -123.2(3) . . . . ?
C23 C8 C21 N1 -4.2(3) . . . . ?
C9 C8 C21 N1 109.3(3) . . . . ?
C27 C22 C23 C24 -1.5(5) . . . . ?
N1 C22 C23 C24 178.8(3) . . . . ?
C27 C22 C23 C8 -179.1(3) . . . . ?
N1 C22 C23 C8 1.3(4) . . . . ?
C7 C8 C23 C24 -56.6(4) . . . . ?
C9 C8 C23 C24 67.0(4) . . . . ?
C21 C8 C23 C24 -175.5(3) . . . . ?
C7 C8 C23 C22 120.6(3) . . . . ?
C9 C8 C23 C22 -115.7(3) . . . . ?
C21 C8 C23 C22 1.7(3) . . . . ?
C22 C23 C24 C25 1.0(5) . . . . ?
C8 C23 C24 C25 178.0(3) . . . . ?
C23 C24 C25 C26 -0.1(6) . . . . ?
C23 C24 C25 C28 -178.3(4) . . . . ?
C24 C25 C26 C27 -0.3(7) . . . . ?
C28 C25 C26 C27 177.9(5) . . . . ?
C23 C22 C27 C26 1.1(6) . . . . ?
N1 C22 C27 C26 -179.3(4) . . . . ?
C25 C26 C27 C22 -0.1(7) . . . . ?
C30 C7 C29 O2 175.7(3) . . . . ?
C8 C7 C29 O2 8.2(5) . . . . ?
C30 C7 C29 C6 -4.6(3) . . . . ?
C8 C7 C29 C6 -172.1(3) . . . . ?
C5 C6 C29 O2 3.3(5) . . . . ?
C1 C6 C29 O2 -177.0(3) . . . . ?
C5 C6 C29 C7 -176.4(3) . . . . ?
C1 C6 C29 C7 3.3(3) . . . . ?
C29 C7 C30 O1 -175.4(3) . . . . ?
C8 C7 C30 O1 -7.5(5) . . . . ?
C29 C7 C30 C1 4.2(3) . . . . ?
C8 C7 C30 C1 172.1(3) . . . . ?
C2 C1 C30 O1 -4.0(5) . . . . ?
C6 C1 C30 O1 177.6(3) . . . . ?
C2 C1 C30 C7 176.4(3) . . . . ?
C6 C1 C30 C7 -2.0(3) . . . . ?
O3 C21 N1 C22 -176.8(3) . . . . ?
C8 C21 N1 C22 5.4(3) . . . . ?
C27 C22 N1 C21 176.0(4) . . . . ?
C23 C22 N1 C21 -4.4(4) . . . . ?
C11 C10 N2 C14 2.7(4) . . . . ?
C11 C10 N2 C9 -176.4(3) . . . . ?
C13 C14 N2 C10 -1.3(4) . . . . ?
C13 C14 N2 C9 177.8(3) . . . . ?
C15 C9 N2 C10 90.1(3) . . . . ?
C8 C9 N2 C10 -40.9(4) . . . . ?
C15 C9 N2 C14 -89.1(3) . . . . ?
C8 C9 N2 C14 140.0(3) . . . . ?
C19 C18 N3 O5 -174.8(4) . . . . ?
C17 C18 N3 O5 4.8(5) . . . . ?
C19 C18 N3 O4 3.7(5) . . . . ?
C17 C18 N3 O4 -176.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O2 0.93 1.95 2.807(3) 153.2 4_576
C13 H13 O1 0.93 2.30 3.186(4) 159.6 4_575
C11 H11 O5 0.93 2.52 3.153(5) 125.8 2_645
C10 H10 O3 0.93 2.11 2.972(4) 153.4 .

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_4b
_audit_block_doi                 10.5517/cc1kkq2x
_database_code_depnum_ccdc_archive 'CCDC 1446989'
_audit_update_record             
;
2016-01-13 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3.12 H2.12 Cl0.12 N0.25 O0.62'
_chemical_formula_weight         57.61

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.7830(18)
_cell_length_b                   13.245(2)
_cell_length_c                   15.8627(18)
_cell_angle_alpha                90
_cell_angle_beta                 94.265(4)
_cell_angle_gamma                90
_cell_volume                     2468.8(6)
_cell_formula_units_Z            32
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5110
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.56
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.191
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6294
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            13308
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.235
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.009
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4338
_reflns_number_gt                3360
_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.
;

_platon_squeeze_void_content     1
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?


_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0679P)²+0.9205P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4338
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1341
_refine_ls_wR_factor_gt          0.1283
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
C1 C 0.8988(2) 0.27743(18) 0.71114(16) 0.0189(5) Uani 1 1 d . . . . .
H1 H 0.9548 0.2955 0.6756 0.023 Uiso 1 1 calc R U . . .
C2 C 0.8997(2) 0.31860(19) 0.79075(16) 0.0227(6) Uani 1 1 d . . . . .
H2 H 0.9564 0.3640 0.8093 0.027 Uiso 1 1 calc R U . . .
C3 C 0.8157(2) 0.29210(19) 0.84317(16) 0.0223(6) Uani 1 1 d . . . . .
H3 H 0.8148 0.3201 0.8969 0.027 Uiso 1 1 calc R U . . .
C4 C 0.7334(2) 0.22365(19) 0.81469(16) 0.0213(6) Uani 1 1 d . . . . .
H4 H 0.6767 0.2047 0.8493 0.026 Uiso 1 1 calc R U . . .
C5 C 0.7355(2) 0.18343(18) 0.73469(15) 0.0172(5) Uani 1 1 d . . . . .
H5 H 0.6803 0.1371 0.7154 0.021 Uiso 1 1 calc R U . . .
C6 C 0.82049(19) 0.16878(17) 0.59734(14) 0.0135(5) Uani 1 1 d . . . . .
H6 H 0.8687 0.2145 0.5670 0.016 Uiso 1 1 calc R U . . .
C7 C 0.88008(19) 0.06658(18) 0.59968(15) 0.0160(5) Uani 1 1 d . . . . .
C8 C 1.0086(3) -0.0434(2) 0.67322(18) 0.0331(7) Uani 1 1 d . . . . .
H8A H 0.9574 -0.0996 0.6659 0.050 Uiso 1 1 calc R U . . .
H8B H 1.0519 -0.0491 0.7267 0.050 Uiso 1 1 calc R U . . .
H8C H 1.0593 -0.0432 0.6286 0.050 Uiso 1 1 calc R U . . .
C9 C 0.70219(18) 0.16575(17) 0.54466(14) 0.0124(5) Uani 1 1 d . . . . .
C10 C 0.64212(19) 0.06221(17) 0.55616(15) 0.0142(5) Uani 1 1 d . . . . .
C11 C 0.66616(18) 0.07635(17) 0.41546(15) 0.0140(5) Uani 1 1 d . . . . .
C12 C 0.6590(2) 0.05777(18) 0.32975(15) 0.0174(5) Uani 1 1 d . . . . .
H12 H 0.6243 -0.0005 0.3076 0.021 Uiso 1 1 calc R U . . .
C13 C 0.7052(2) 0.12847(19) 0.27751(15) 0.0190(5) Uani 1 1 d . . . . .
H13 H 0.6999 0.1190 0.2193 0.023 Uiso 1 1 calc R U . . .
C14 C 0.7595(2) 0.21356(18) 0.31259(15) 0.0197(5) Uani 1 1 d . . . . .
C15 C 0.7669(2) 0.23287(18) 0.39870(15) 0.0166(5) Uani 1 1 d . . . . .
H15 H 0.8026 0.2906 0.4210 0.020 Uiso 1 1 calc R U . . .
C16 C 0.71901(18) 0.16270(17) 0.45030(14) 0.0134(5) Uani 1 1 d . . . . .
C17 C 0.62744(19) 0.25339(17) 0.56525(14) 0.0131(5) Uani 1 1 d . . . . .
C18 C 0.50691(19) 0.25313(17) 0.56404(13) 0.0128(5) Uani 1 1 d . . . . .
C19 C 0.47048(19) 0.35921(17) 0.58402(14) 0.0143(5) Uani 1 1 d . . . . .
C20 C 0.3649(2) 0.39920(18) 0.59203(15) 0.0172(5) Uani 1 1 d . . . . .
H20 H 0.3001 0.3589 0.5861 0.021 Uiso 1 1 calc R U . . .
C21 C 0.3569(2) 0.50342(19) 0.60953(15) 0.0188(5) Uani 1 1 d . . . . .
H21 H 0.2860 0.5323 0.6155 0.023 Uiso 1 1 calc R U . . .
C22 C 0.4533(2) 0.56298(18) 0.61789(15) 0.0200(5) Uani 1 1 d . . . . .
H22 H 0.4466 0.6314 0.6298 0.024 Uiso 1 1 calc R U . . .
C23 C 0.5612(2) 0.52145(17) 0.60867(15) 0.0173(5) Uani 1 1 d . . . . .
H23 H 0.6262 0.5615 0.6137 0.021 Uiso 1 1 calc R U . . .
C24 C 0.5681(2) 0.41984(17) 0.59204(14) 0.0150(5) Uani 1 1 d . . . . .
C25 C 0.66879(19) 0.35402(17) 0.57616(14) 0.0132(5) Uani 1 1 d . . . . .
Cl1 Cl 0.81660(7) 0.30034(5) 0.24448(4) 0.0359(2) Uani 1 1 d . . . . .
N1 N 0.62207(16) 0.01871(14) 0.47937(12) 0.0144(4) Uani 1 1 d . . . . .
H1A H 0.5909 -0.0449 0.4734 0.017 Uiso 1 1 d R U . . .
N2 N 0.81722(16) 0.21101(14) 0.68447(12) 0.0132(4) Uani 1 1 d . . . . .
O1 O 0.94352(15) 0.05045(13) 0.67082(11) 0.0246(4) Uani 1 1 d . . . . .
O2 O 0.87215(15) 0.00948(13) 0.54046(11) 0.0262(4) Uani 1 1 d . . . . .
O3 O 0.43788(13) 0.18255(12) 0.54801(10) 0.0178(4) Uani 1 1 d . . . . .
O4 O 0.76883(13) 0.38570(12) 0.57272(10) 0.0186(4) Uani 1 1 d . . . . .
O5 O 0.61848(14) 0.02538(12) 0.62361(10) 0.0179(4) Uani 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
C1 N2 1.348(3) . ?
C1 C2 1.375(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.384(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(4) . ?
C4 H4 0.9300 . ?
C5 N2 1.345(3) . ?
C5 H5 0.9300 . ?
C6 N2 1.494(3) . ?
C6 C7 1.524(3) . ?
C6 C9 1.572(3) . ?
C6 H6 0.9800 . ?
C7 O2 1.204(3) . ?
C7 O1 1.324(3) . ?
C8 O1 1.459(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C17 1.507(3) . ?
C9 C16 1.525(3) . ?
C9 C10 1.560(3) . ?
C10 O5 1.227(3) . ?
C10 N1 1.352(3) . ?
C11 C12 1.378(3) . ?
C11 C16 1.396(3) . ?
C11 N1 1.400(3) . ?
C12 C13 1.388(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.392(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(3) . ?
C14 Cl1 1.746(2) . ?
C15 C16 1.386(3) . ?
C15 H15 0.9300 . ?
C17 C18 1.419(3) . ?
C17 C25 1.425(3) . ?
C18 O3 1.253(3) . ?
C18 C19 1.510(3) . ?
C19 C20 1.367(3) . ?
C19 C24 1.400(3) . ?
C20 C21 1.413(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.381(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.403(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.375(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.509(3) . ?
C25 O4 1.256(3) . ?
N1 H1A 0.9213 . ?

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
N2 C1 C2 120.2(2) . . ?
N2 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C1 C2 C3 119.6(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 119.1(2) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N2 C5 C4 120.2(2) . . ?
N2 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
N2 C6 C7 110.70(18) . . ?
N2 C6 C9 114.74(18) . . ?
C7 C6 C9 112.28(18) . . ?
N2 C6 H6 106.1 . . ?
C7 C6 H6 106.1 . . ?
C9 C6 H6 106.1 . . ?
O2 C7 O1 124.7(2) . . ?
O2 C7 C6 122.0(2) . . ?
O1 C7 C6 113.21(19) . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C17 C9 C16 110.72(18) . . ?
C17 C9 C10 111.97(18) . . ?
C16 C9 C10 100.64(17) . . ?
C17 C9 C6 111.99(18) . . ?
C16 C9 C6 110.35(18) . . ?
C10 C9 C6 110.64(18) . . ?
O5 C10 N1 125.5(2) . . ?
O5 C10 C9 125.9(2) . . ?
N1 C10 C9 108.64(19) . . ?
C12 C11 C16 122.0(2) . . ?
C12 C11 N1 128.2(2) . . ?
C16 C11 N1 109.8(2) . . ?
C11 C12 C13 118.1(2) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
C12 C13 C14 119.8(2) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 122.5(2) . . ?
C15 C14 Cl1 119.31(19) . . ?
C13 C14 Cl1 118.19(19) . . ?
C16 C15 C14 117.4(2) . . ?
C16 C15 H15 121.3 . . ?
C14 C15 H15 121.3 . . ?
C15 C16 C11 120.3(2) . . ?
C15 C16 C9 130.6(2) . . ?
C11 C16 C9 108.87(19) . . ?
C18 C17 C25 109.67(19) . . ?
C18 C17 C9 126.5(2) . . ?
C25 C17 C9 123.13(19) . . ?
O3 C18 C17 129.7(2) . . ?
O3 C18 C19 123.1(2) . . ?
C17 C18 C19 107.15(19) . . ?
C20 C19 C24 121.1(2) . . ?
C20 C19 C18 130.9(2) . . ?
C24 C19 C18 107.96(19) . . ?
C19 C20 C21 118.1(2) . . ?
C19 C20 H20 120.9 . . ?
C21 C20 H20 120.9 . . ?
C22 C21 C20 120.7(2) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C23 120.7(2) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C24 C23 C22 118.1(2) . . ?
C24 C23 H23 121.0 . . ?
C22 C23 H23 121.0 . . ?
C23 C24 C19 121.3(2) . . ?
C23 C24 C25 131.0(2) . . ?
C19 C24 C25 107.72(19) . . ?
O4 C25 C17 128.3(2) . . ?
O4 C25 C24 124.5(2) . . ?
C17 C25 C24 107.13(19) . . ?
C10 N1 C11 111.75(19) . . ?
C10 N1 H1A 121.6 . . ?
C11 N1 H1A 126.2 . . ?
C5 N2 C1 121.1(2) . . ?
C5 N2 C6 121.00(19) . . ?
C1 N2 C6 117.89(19) . . ?
C7 O1 C8 114.97(19) . . ?

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
N2 C1 C2 C3 -0.5(4) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 N2 -0.2(4) . . . . ?
N2 C6 C7 O2 164.3(2) . . . . ?
C9 C6 C7 O2 34.6(3) . . . . ?
N2 C6 C7 O1 -18.4(3) . . . . ?
C9 C6 C7 O1 -148.1(2) . . . . ?
N2 C6 C9 C17 33.6(3) . . . . ?
C7 C6 C9 C17 161.18(19) . . . . ?
N2 C6 C9 C16 157.46(18) . . . . ?
C7 C6 C9 C16 -75.0(2) . . . . ?
N2 C6 C9 C10 -92.0(2) . . . . ?
C7 C6 C9 C10 35.5(2) . . . . ?
C17 C9 C10 O5 -68.4(3) . . . . ?
C16 C9 C10 O5 173.9(2) . . . . ?
C6 C9 C10 O5 57.3(3) . . . . ?
C17 C9 C10 N1 112.6(2) . . . . ?
C16 C9 C10 N1 -5.0(2) . . . . ?
C6 C9 C10 N1 -121.7(2) . . . . ?
C16 C11 C12 C13 -0.7(3) . . . . ?
N1 C11 C12 C13 177.1(2) . . . . ?
C11 C12 C13 C14 1.8(3) . . . . ?
C12 C13 C14 C15 -2.0(4) . . . . ?
C12 C13 C14 Cl1 179.88(18) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
Cl1 C14 C15 C16 179.07(18) . . . . ?
C14 C15 C16 C11 0.2(3) . . . . ?
C14 C15 C16 C9 -173.3(2) . . . . ?
C12 C11 C16 C15 -0.3(3) . . . . ?
N1 C11 C16 C15 -178.5(2) . . . . ?
C12 C11 C16 C9 174.5(2) . . . . ?
N1 C11 C16 C9 -3.7(2) . . . . ?
C17 C9 C16 C15 60.7(3) . . . . ?
C10 C9 C16 C15 179.2(2) . . . . ?
C6 C9 C16 C15 -63.9(3) . . . . ?
C17 C9 C16 C11 -113.4(2) . . . . ?
C10 C9 C16 C11 5.2(2) . . . . ?
C6 C9 C16 C11 122.0(2) . . . . ?
C16 C9 C17 C18 88.4(3) . . . . ?
C10 C9 C17 C18 -23.0(3) . . . . ?
C6 C9 C17 C18 -148.0(2) . . . . ?
C16 C9 C17 C25 -81.4(3) . . . . ?
C10 C9 C17 C25 167.2(2) . . . . ?
C6 C9 C17 C25 42.3(3) . . . . ?
C25 C17 C18 O3 172.5(2) . . . . ?
C9 C17 C18 O3 1.6(4) . . . . ?
C25 C17 C18 C19 -5.8(2) . . . . ?
C9 C17 C18 C19 -176.7(2) . . . . ?
O3 C18 C19 C20 2.7(4) . . . . ?
C17 C18 C19 C20 -178.8(2) . . . . ?
O3 C18 C19 C24 -175.4(2) . . . . ?
C17 C18 C19 C24 3.0(2) . . . . ?
C24 C19 C20 C21 -0.7(3) . . . . ?
C18 C19 C20 C21 -178.6(2) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C20 C21 C22 C23 0.4(4) . . . . ?
C21 C22 C23 C24 -0.7(3) . . . . ?
C22 C23 C24 C19 0.3(3) . . . . ?
C22 C23 C24 C25 177.7(2) . . . . ?
C20 C19 C24 C23 0.4(3) . . . . ?
C18 C19 C24 C23 178.7(2) . . . . ?
C20 C19 C24 C25 -177.6(2) . . . . ?
C18 C19 C24 C25 0.8(2) . . . . ?
C18 C17 C25 O4 -172.9(2) . . . . ?
C9 C17 C25 O4 -1.6(4) . . . . ?
C18 C17 C25 C24 6.3(2) . . . . ?
C9 C17 C25 C24 177.54(19) . . . . ?
C23 C24 C25 O4 -2.7(4) . . . . ?
C19 C24 C25 O4 175.0(2) . . . . ?
C23 C24 C25 C17 178.0(2) . . . . ?
C19 C24 C25 C17 -4.3(2) . . . . ?
O5 C10 N1 C11 -175.7(2) . . . . ?
C9 C10 N1 C11 3.2(2) . . . . ?
C12 C11 N1 C10 -177.8(2) . . . . ?
C16 C11 N1 C10 0.3(3) . . . . ?
C4 C5 N2 C1 0.6(3) . . . . ?
C4 C5 N2 C6 -179.6(2) . . . . ?
C2 C1 N2 C5 -0.2(3) . . . . ?
C2 C1 N2 C6 180.0(2) . . . . ?
C7 C6 N2 C5 -83.6(2) . . . . ?
C9 C6 N2 C5 44.7(3) . . . . ?
C7 C6 N2 C1 96.2(2) . . . . ?
C9 C6 N2 C1 -135.4(2) . . . . ?
O2 C7 O1 C8 1.5(4) . . . . ?
C6 C7 O1 C8 -175.8(2) . . . . ?

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.059

