# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

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

data_4w
_database_code_depnum_ccdc_archive 'CCDC 1420055'
_audit_update_record             
;
2015-09-17 deposited with the CCDC.
2015-10-14 downloaded from the CCDC.
;
_chemical_name_systematic        4w
_chemical_name_common            Hamada_FK87_02_06_14
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 Br N5 O5 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         618.46

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   17.8147(8)
_cell_length_b                   7.4508(5)
_cell_length_c                   21.5768(11)
_cell_angle_alpha                90
_cell_angle_beta                 108.369(3)
_cell_angle_gamma                90
_cell_volume                     2718.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4127
_cell_measurement_theta_min      4.3182
_cell_measurement_theta_max      64.9366
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1256

_exptl_absorpt_coefficient_mu    3.191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              'Incoatec Cu-ImS'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'mirror optics'

_diffrn_measurement_device_type  'Bruker X8 Prospector'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            16961
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_theta_min         4.32
_diffrn_reflns_theta_max         66.62
_diffrn_reflns_theta_full        66.62
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25

_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.
;

_reflns_number_total             4701
_reflns_number_gt                3192
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1241
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_number_reflns         4701
_refine_ls_number_parameters     402
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0509P)²+1.4870P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.550
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2012.4.0.0'
_computing_cell_refinement       'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 3.1'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O6A 0.8840(4) 0.9984(12) 0.0225(3) 0.0812(18) Uani d P 0.733(4) A 1
C C27A 1.0103(10) 0.822(2) 0.0760(8) 0.107(6) Uani d P 0.733(4) A 1
H H27A 0.9966 0.7173 0.0489 0.16 Uiso calc PR 0.733(4) A 1
H H27B 1.0476 0.7903 0.1173 0.16 Uiso calc PR 0.733(4) A 1
H H27C 1.0334 0.9101 0.055 0.16 Uiso calc PR 0.733(4) A 1
C C28A 0.9700(8) 1.0969(17) 0.1368(6) 0.144(6) Uani d P 0.733(4) A 1
H H28A 0.9987 1.1671 0.1146 0.216 Uiso calc PR 0.733(4) A 1
H H28B 1.0055 1.0557 0.1777 0.216 Uiso calc PR 0.733(4) A 1
H H28C 0.9292 1.1692 0.1446 0.216 Uiso calc PR 0.733(4) A 1
S S1A 0.92654(8) 0.9097(3) 0.08793(7) 0.0717(7) Uani d P 0.733(4) A 1
O O6B 0.8642(10) 0.980(3) 0.0420(8) 0.066(5) Uani d P 0.267(4) A 2
C C27B 1.006(2) 0.801(4) 0.0723(17) 0.075(12) Uani d P 0.267(4) A 2
H H27D 0.9773 0.7093 0.0871 0.112 Uiso calc PR 0.267(4) A 2
H H27E 1.0593 0.8053 0.1008 0.112 Uiso calc PR 0.267(4) A 2
H H27F 1.0053 0.7733 0.0287 0.112 Uiso calc PR 0.267(4) A 2
C C28B 0.9661(17) 1.017(4) 0.1523(14) 0.078(8) Uani d P 0.267(4) A 2
H H28D 0.9384 1.1155 0.1636 0.117 Uiso calc PR 0.267(4) A 2
H H28E 1.0211 1.0232 0.1774 0.117 Uiso calc PR 0.267(4) A 2
H H28F 0.9443 0.9058 0.1616 0.117 Uiso calc PR 0.267(4) A 2
S S1B 0.9563(3) 1.0263(7) 0.0728(2) 0.087(2) Uani d P 0.267(4) A 2
Br Br1 0.75840(3) 0.98580(7) 0.14528(2) 0.0874(2) Uani d . 1.0 . .
O O1 0.50029(16) 1.0323(4) 0.31808(14) 0.0880(9) Uani d . 1.0 . .
O O4 0.14821(13) 0.9299(3) 0.22904(10) 0.0569(6) Uani d . 1.0 . .
N N3 0.19356(14) 0.6938(3) 0.13008(11) 0.0440(6) Uani d . 1.0 . .
O O3 0.37805(19) 0.6137(6) -0.06911(15) 0.1039(11) Uani d . 1.0 . .
O O2 0.2677(2) 0.5115(5) -0.12826(14) 0.1019(11) Uani d . 1.0 . .
C C9 0.34965(17) 0.8937(4) 0.26436(14) 0.0442(7) Uani d . 1.0 . .
H H9 0.3632 0.9386 0.3067 0.053 Uiso calc R 1.0 . .
N N5 0.26486(16) 0.6475(4) 0.42319(12) 0.0530(7) Uani d . 1.0 . .
H H5 0.2971 0.5924 0.4559 0.064 Uiso calc R 1.0 . .
N N1 0.31997(13) 0.7711(3) 0.14325(11) 0.0392(6) Uani d . 1.0 . .
N N2 0.39384(14) 0.8316(3) 0.17156(12) 0.0434(6) Uani d . 1.0 . .
C C4 0.67434(19) 0.9755(5) 0.18175(16) 0.0584(9) Uani d . 1.0 . .
C C5 0.6659(2) 1.1110(6) 0.22090(18) 0.0675(10) Uani d . 1.0 . .
H H5A 0.7004 1.2083 0.2294 0.081 Uiso calc R 1.0 . .
C C6 0.6052(2) 1.1025(6) 0.24792(18) 0.0652(10) Uani d . 1.0 . .
H H6 0.6001 1.1926 0.2761 0.078 Uiso calc R 1.0 . .
C C1 0.55216(17) 0.9616(5) 0.23354(15) 0.0493(8) Uani d . 1.0 . .
C C7 0.48877(19) 0.9645(5) 0.26464(17) 0.0535(8) Uani d . 1.0 . .
C C8 0.40761(17) 0.8895(4) 0.23140(14) 0.0438(7) Uani d . 1.0 . .
C C10 0.27505(17) 0.8331(4) 0.23480(13) 0.0402(7) Uani d . 1.0 . .
C C18 0.20812(17) 0.8520(4) 0.26295(14) 0.0417(7) Uani d . 1.0 . .
C C19 0.21591(17) 0.7820(4) 0.32659(13) 0.0402(7) Uani d . 1.0 . .
C C20 0.15603(18) 0.7878(4) 0.35906(14) 0.0437(7) Uani d . 1.0 . .
C C25 0.18940(19) 0.7020(4) 0.41917(14) 0.0495(8) Uani d . 1.0 . .
C C24 0.1476(3) 0.6794(6) 0.46369(17) 0.0697(11) Uani d . 1.0 . .
H H24 0.17 0.6219 0.5035 0.084 Uiso calc R 1.0 . .
C C23 0.0720(3) 0.7459(6) 0.4458(2) 0.0795(12) Uani d . 1.0 . .
H H23 0.0425 0.7337 0.4743 0.095 Uiso calc R 1.0 . .
C C26 0.28024(19) 0.6936(4) 0.36837(14) 0.0470(7) Uani d . 1.0 . .
H H26 0.3272 0.6696 0.3597 0.056 Uiso calc R 1.0 . .
C C22 0.0384(2) 0.8305(6) 0.38661(19) 0.0721(11) Uani d . 1.0 . .
H H22 -0.013 0.8738 0.3763 0.087 Uiso calc R 1.0 . .
C C21 0.07894(18) 0.8526(5) 0.34244(17) 0.0555(9) Uani d . 1.0 . .
H H21 0.0555 0.9091 0.3026 0.067 Uiso calc R 1.0 . .
C C11 0.25801(16) 0.7634(4) 0.17043(14) 0.0402(7) Uani d . 1.0 . .
C C12 0.21241(17) 0.6544(4) 0.07390(14) 0.0427(7) Uani d . 1.0 . .
C C13 0.1658(2) 0.5781(5) 0.01541(16) 0.0534(8) Uani d . 1.0 . .
H H13 0.1138 0.5449 0.0097 0.064 Uiso calc R 1.0 . .
C C14 0.1988(2) 0.5533(5) -0.03350(16) 0.0559(9) Uani d . 1.0 . .
H H14 0.1692 0.5019 -0.0729 0.067 Uiso calc R 1.0 . .
C C15 0.2770(2) 0.6053(5) -0.02404(15) 0.0513(8) Uani d . 1.0 . .
C C16 0.32530(19) 0.6803(4) 0.03219(14) 0.0482(8) Uani d . 1.0 . .
H H16 0.3773 0.7134 0.0374 0.058 Uiso calc R 1.0 . .
C C17 0.29074(17) 0.7029(4) 0.08074(13) 0.0418(7) Uani d . 1.0 . .
N N4 0.3099(2) 0.5747(5) -0.07765(15) 0.0689(9) Uani d . 1.0 . .
C C2 0.5631(2) 0.8259(5) 0.1943(2) 0.0675(10) Uani d . 1.0 . .
H H2 0.5283 0.7293 0.1848 0.081 Uiso calc R 1.0 . .
C C3 0.6249(2) 0.8306(6) 0.1687(2) 0.0754(12) Uani d . 1.0 . .
H H3 0.6328 0.7368 0.143 0.091 Uiso calc R 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O6A S1A . 1.526(7) ?
C27A S1A . 1.721(16) ?
C27A H27A . 0.96 ?
C27A H27B . 0.96 ?
C27A H27C . 0.96 ?
C28A S1A . 1.773(13) ?
C28A H28A . 0.96 ?
C28A H28B . 0.96 ?
C28A H28C . 0.96 ?
O6B S1B . 1.603(19) ?
C27B S1B . 1.90(3) ?
C27B H27D . 0.96 ?
C27B H27E . 0.96 ?
C27B H27F . 0.96 ?
C28B S1B . 1.67(3) ?
C28B H28D . 0.96 ?
C28B H28E . 0.96 ?
C28B H28F . 0.96 ?
Br1 C4 . 1.900(3) ?
O1 C7 . 1.216(4) ?
O4 C18 . 1.232(4) ?
N3 C11 . 1.310(4) ?
N3 C12 . 1.388(4) ?
O3 N4 . 1.204(4) ?
O2 N4 . 1.209(4) ?
C9 C10 . 1.357(4) ?
C9 C8 . 1.427(4) ?
C9 H9 . 0.93 ?
N5 C26 . 1.340(4) ?
N5 C25 . 1.381(4) ?
N5 H5 . 0.86 ?
N1 N2 . 1.342(3) ?
N1 C17 . 1.380(4) ?
N1 C11 . 1.405(3) ?
N2 C8 . 1.309(4) ?
C4 C5 . 1.355(5) ?
C4 C3 . 1.365(5) ?
C5 C6 . 1.382(5) ?
C5 H5A . 0.93 ?
C6 C1 . 1.381(5) ?
C6 H6 . 0.93 ?
C1 C2 . 1.372(5) ?
C1 C7 . 1.484(4) ?
C7 C8 . 1.505(4) ?
C10 C11 . 1.423(4) ?
C10 C18 . 1.506(4) ?
C18 C19 . 1.434(4) ?
C19 C26 . 1.382(4) ?
C19 C20 . 1.450(4) ?
C20 C21 . 1.392(4) ?
C20 C25 . 1.399(4) ?
C25 C24 . 1.399(4) ?
C24 C23 . 1.371(6) ?
C24 H24 . 0.93 ?
C23 C22 . 1.380(6) ?
C23 H23 . 0.93 ?
C26 H26 . 0.93 ?
C22 C21 . 1.375(5) ?
C22 H22 . 0.93 ?
C21 H21 . 0.93 ?
C12 C13 . 1.394(4) ?
C12 C17 . 1.404(4) ?
C13 C14 . 1.373(5) ?
C13 H13 . 0.93 ?
C14 C15 . 1.397(5) ?
C14 H14 . 0.93 ?
C15 C16 . 1.366(5) ?
C15 N4 . 1.471(4) ?
C16 C17 . 1.383(4) ?
C16 H16 . 0.93 ?
C2 C3 . 1.380(5) ?
C2 H2 . 0.93 ?
C3 H3 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O6A S1A C27A . . 103.1(5) ?
O6A S1A C28A . . 101.9(5) ?
C27A S1A C28A . . 98.7(8) ?
S1B C27B H27D . . 109.5 ?
S1B C27B H27E . . 109.5 ?
H27D C27B H27E . . 109.5 ?
S1B C27B H27F . . 109.5 ?
H27D C27B H27F . . 109.5 ?
H27E C27B H27F . . 109.5 ?
S1B C28B H28D . . 109.5 ?
S1B C28B H28E . . 109.5 ?
H28D C28B H28E . . 109.5 ?
S1B C28B H28F . . 109.5 ?
H28D C28B H28F . . 109.5 ?
H28E C28B H28F . . 109.5 ?
O6B S1B C28B . . 100.3(12) ?
O6B S1B C27B . . 102.8(16) ?
C28B S1B C27B . . 94.0(14) ?
C11 N3 C12 . . 105.2(2) ?
C10 C9 C8 . . 120.9(3) ?
C10 C9 H9 . . 119.6 ?
C8 C9 H9 . . 119.6 ?
C26 N5 C25 . . 109.6(3) ?
C26 N5 H5 . . 125.2 ?
C25 N5 H5 . . 125.2 ?
N2 N1 C17 . . 125.6(2) ?
N2 N1 C11 . . 127.6(2) ?
C17 N1 C11 . . 106.8(2) ?
C8 N2 N1 . . 114.3(2) ?
C5 C4 C3 . . 121.8(3) ?
C5 C4 Br1 . . 119.0(3) ?
C3 C4 Br1 . . 119.2(3) ?
C4 C5 C6 . . 118.9(4) ?
C4 C5 H5A . . 120.5 ?
C6 C5 H5A . . 120.5 ?
C1 C6 C5 . . 120.8(3) ?
C1 C6 H6 . . 119.6 ?
C5 C6 H6 . . 119.6 ?
C2 C1 C6 . . 118.6(3) ?
C2 C1 C7 . . 124.5(3) ?
C6 C1 C7 . . 116.8(3) ?
O1 C7 C1 . . 120.7(3) ?
O1 C7 C8 . . 117.1(3) ?
C1 C7 C8 . . 122.2(3) ?
N2 C8 C9 . . 124.0(3) ?
N2 C8 C7 . . 116.5(3) ?
C9 C8 C7 . . 119.5(3) ?
C9 C10 C11 . . 117.1(3) ?
C9 C10 C18 . . 124.2(3) ?
C11 C10 C18 . . 118.4(3) ?
O4 C18 C19 . . 123.0(3) ?
O4 C18 C10 . . 116.9(3) ?
C19 C18 C10 . . 120.2(3) ?
C26 C19 C18 . . 127.5(3) ?
C26 C19 C20 . . 106.5(3) ?
C18 C19 C20 . . 126.0(3) ?
C21 C20 C25 . . 119.6(3) ?
C21 C20 C19 . . 134.6(3) ?
C25 C20 C19 . . 105.8(3) ?
N5 C25 C24 . . 129.8(3) ?
N5 C25 C20 . . 108.3(3) ?
C24 C25 C20 . . 121.9(3) ?
C23 C24 C25 . . 116.8(4) ?
C23 C24 H24 . . 121.6 ?
C25 C24 H24 . . 121.6 ?
C24 C23 C22 . . 121.8(4) ?
C24 C23 H23 . . 119.1 ?
C22 C23 H23 . . 119.1 ?
N5 C26 C19 . . 109.9(3) ?
N5 C26 H26 . . 125.1 ?
C19 C26 H26 . . 125.1 ?
C21 C22 C23 . . 121.8(4) ?
C21 C22 H22 . . 119.1 ?
C23 C22 H22 . . 119.1 ?
C22 C21 C20 . . 118.1(3) ?
C22 C21 H21 . . 120.9 ?
C20 C21 H21 . . 120.9 ?
N3 C11 N1 . . 112.2(2) ?
N3 C11 C10 . . 131.8(3) ?
N1 C11 C10 . . 116.0(3) ?
N3 C12 C13 . . 129.7(3) ?
N3 C12 C17 . . 111.1(3) ?
C13 C12 C17 . . 119.2(3) ?
C14 C13 C12 . . 118.3(3) ?
C14 C13 H13 . . 120.9 ?
C12 C13 H13 . . 120.9 ?
C13 C14 C15 . . 119.9(3) ?
C13 C14 H14 . . 120.0 ?
C15 C14 H14 . . 120.0 ?
C16 C15 C14 . . 124.3(3) ?
C16 C15 N4 . . 117.8(3) ?
C14 C15 N4 . . 117.9(3) ?
C15 C16 C17 . . 114.6(3) ?
C15 C16 H16 . . 122.7 ?
C17 C16 H16 . . 122.7 ?
N1 C17 C16 . . 131.6(3) ?
N1 C17 C12 . . 104.7(2) ?
C16 C17 C12 . . 123.7(3) ?
O3 N4 O2 . . 122.8(3) ?
O3 N4 C15 . . 118.4(3) ?
O2 N4 C15 . . 118.8(3) ?
C1 C2 C3 . . 121.0(3) ?
C1 C2 H2 . . 119.5 ?
C3 C2 H2 . . 119.5 ?
C4 C3 C2 . . 118.8(4) ?
C4 C3 H3 . . 120.6 ?
C2 C3 H3 . . 120.6 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C17 N1 N2 C8 . . . . -179.9(3) ?
C11 N1 N2 C8 . . . . -0.1(4) ?
C3 C4 C5 C6 . . . . -0.4(6) ?
Br1 C4 C5 C6 . . . . -179.3(3) ?
C4 C5 C6 C1 . . . . -2.3(6) ?
C5 C6 C1 C2 . . . . 3.0(6) ?
C5 C6 C1 C7 . . . . -179.7(3) ?
C2 C1 C7 O1 . . . . 146.2(4) ?
C6 C1 C7 O1 . . . . -31.0(5) ?
C2 C1 C7 C8 . . . . -35.5(5) ?
C6 C1 C7 C8 . . . . 147.4(3) ?
N1 N2 C8 C9 . . . . -1.5(4) ?
N1 N2 C8 C7 . . . . -178.0(3) ?
C10 C9 C8 N2 . . . . 1.2(5) ?
C10 C9 C8 C7 . . . . 177.6(3) ?
O1 C7 C8 N2 . . . . 174.0(3) ?
C1 C7 C8 N2 . . . . -4.3(5) ?
O1 C7 C8 C9 . . . . -2.6(5) ?
C1 C7 C8 C9 . . . . 179.0(3) ?
C8 C9 C10 C11 . . . . 0.9(4) ?
C8 C9 C10 C18 . . . . -172.7(3) ?
C9 C10 C18 O4 . . . . 123.3(3) ?
C11 C10 C18 O4 . . . . -50.3(4) ?
C9 C10 C18 C19 . . . . -56.4(4) ?
C11 C10 C18 C19 . . . . 130.1(3) ?
O4 C18 C19 C26 . . . . -179.8(3) ?
C10 C18 C19 C26 . . . . -0.2(5) ?
O4 C18 C19 C20 . . . . 1.6(5) ?
C10 C18 C19 C20 . . . . -178.8(3) ?
C26 C19 C20 C21 . . . . -178.0(4) ?
C18 C19 C20 C21 . . . . 0.9(6) ?
C26 C19 C20 C25 . . . . 0.3(3) ?
C18 C19 C20 C25 . . . . 179.2(3) ?
C26 N5 C25 C24 . . . . 178.3(3) ?
C26 N5 C25 C20 . . . . -0.5(4) ?
C21 C20 C25 N5 . . . . 178.7(3) ?
C19 C20 C25 N5 . . . . 0.1(3) ?
C21 C20 C25 C24 . . . . -0.2(5) ?
C19 C20 C25 C24 . . . . -178.9(3) ?
N5 C25 C24 C23 . . . . -178.9(4) ?
C20 C25 C24 C23 . . . . -0.2(5) ?
C25 C24 C23 C22 . . . . 0.3(6) ?
C25 N5 C26 C19 . . . . 0.7(4) ?
C18 C19 C26 N5 . . . . -179.5(3) ?
C20 C19 C26 N5 . . . . -0.7(4) ?
C24 C23 C22 C21 . . . . 0.0(7) ?
C23 C22 C21 C20 . . . . -0.4(6) ?
C25 C20 C21 C22 . . . . 0.5(5) ?
C19 C20 C21 C22 . . . . 178.7(4) ?
C12 N3 C11 N1 . . . . -0.4(3) ?
C12 N3 C11 C10 . . . . 178.5(3) ?
N2 N1 C11 N3 . . . . -178.9(3) ?
C17 N1 C11 N3 . . . . 0.9(3) ?
N2 N1 C11 C10 . . . . 2.1(4) ?
C17 N1 C11 C10 . . . . -178.1(3) ?
C9 C10 C11 N3 . . . . 178.9(3) ?
C18 C10 C11 N3 . . . . -7.1(5) ?
C9 C10 C11 N1 . . . . -2.3(4) ?
C18 C10 C11 N1 . . . . 171.7(3) ?
C11 N3 C12 C13 . . . . 179.9(3) ?
C11 N3 C12 C17 . . . . -0.3(3) ?
N3 C12 C13 C14 . . . . 179.8(3) ?
C17 C12 C13 C14 . . . . 0.0(5) ?
C12 C13 C14 C15 . . . . -0.5(5) ?
C13 C14 C15 C16 . . . . 0.6(5) ?
C13 C14 C15 N4 . . . . 179.5(3) ?
C14 C15 C16 C17 . . . . -0.3(5) ?
N4 C15 C16 C17 . . . . -179.2(3) ?
N2 N1 C17 C16 . . . . -0.8(5) ?
C11 N1 C17 C16 . . . . 179.4(3) ?
N2 N1 C17 C12 . . . . 178.8(3) ?
C11 N1 C17 C12 . . . . -1.0(3) ?
C15 C16 C17 N1 . . . . 179.4(3) ?
C15 C16 C17 C12 . . . . -0.2(5) ?
N3 C12 C17 N1 . . . . 0.9(3) ?
C13 C12 C17 N1 . . . . -179.4(3) ?
N3 C12 C17 C16 . . . . -179.5(3) ?
C13 C12 C17 C16 . . . . 0.3(5) ?
C16 C15 N4 O3 . . . . 1.4(5) ?
C14 C15 N4 O3 . . . . -177.6(4) ?
C16 C15 N4 O2 . . . . -178.7(4) ?
C14 C15 N4 O2 . . . . 2.4(5) ?
C6 C1 C2 C3 . . . . -1.0(6) ?
C7 C1 C2 C3 . . . . -178.1(4) ?
C5 C4 C3 C2 . . . . 2.3(6) ?
Br1 C4 C3 C2 . . . . -178.7(3) ?
C1 C2 C3 C4 . . . . -1.6(6) ?

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

data_4y
_database_code_depnum_ccdc_archive 'CCDC 1420056'
_audit_update_record             
;
2015-09-17 deposited with the CCDC.
2015-10-14 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C26 H14 Br F N4 O2'
_chemical_formula_moiety         'C26 H14 Br F N4 O2'
_chemical_formula_weight         513.32
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   14.361(6)
_cell_length_b                   14.051(6)
_cell_length_c                   11.274(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 108.430(7)
_cell_angle_gamma                90.0000
_cell_volume                     2158.2(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3417
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      26.34
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032.00
_exptl_absorpt_coefficient_mu    1.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.057
_exptl_absorpt_correction_T_max  0.677

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            18659
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             4380
_reflns_number_gt                2434
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1231
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4380
_refine_ls_number_parameters     307
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0630P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.002
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.540
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Br1 Br -0.46409(3) 1.00320(3) -0.32765(4) 0.0898(2) Uani 1.0 4 d . . .
F1 F -0.27713(12) 0.77189(14) 0.69944(18) 0.0864(6) Uani 1.0 4 d . . .
O1 O -0.01387(15) 1.08270(15) 0.0948(2) 0.0713(6) Uani 1.0 4 d . . .
O2 O 0.21721(13) 0.91244(13) 0.56801(18) 0.0569(5) Uani 1.0 4 d . . .
N1 N -0.00005(15) 0.84038(16) 0.5561(3) 0.0524(6) Uani 1.0 4 d . . .
N2 N -0.09938(14) 0.90223(14) 0.3743(2) 0.0472(6) Uani 1.0 4 d . . .
N3 N -0.12682(15) 0.94686(15) 0.2621(2) 0.0497(6) Uani 1.0 4 d . . .
N4 N 0.2366(2) 0.67628(16) 0.2979(3) 0.0662(7) Uani 1.0 4 d . . .
C1 C -0.3451(3) 1.0085(2) -0.1938(3) 0.0593(8) Uani 1.0 4 d . . .
C2 C -0.3157(3) 0.9314(3) -0.1148(3) 0.0691(9) Uani 1.0 4 d . . .
C3 C -0.2291(3) 0.9368(2) -0.0160(3) 0.0626(8) Uani 1.0 4 d . . .
C4 C -0.1716(2) 1.01843(18) 0.0025(3) 0.0483(7) Uani 1.0 4 d . . .
C5 C -0.20179(19) 1.09340(19) -0.0801(3) 0.0522(7) Uani 1.0 4 d . . .
C6 C -0.2889(2) 1.0897(2) -0.1769(3) 0.0568(8) Uani 1.0 4 d . . .
C7 C -0.0769(2) 1.0268(2) 0.1030(3) 0.0532(7) Uani 1.0 4 d . . .
C8 C -0.0535(2) 0.96865(19) 0.2206(3) 0.0489(7) Uani 1.0 4 d . . .
C9 C 0.04683(19) 0.9449(2) 0.2844(3) 0.0537(7) Uani 1.0 4 d . . .
C10 C 0.07213(18) 0.90032(18) 0.3964(3) 0.0486(7) Uani 1.0 4 d . . .
C11 C -0.00344(18) 0.87957(19) 0.4486(3) 0.0485(7) Uani 1.0 4 d . . .
C12 C -0.09770(19) 0.83606(18) 0.5532(3) 0.0495(7) Uani 1.0 4 d . . .
C13 C -0.1366(2) 0.80236(19) 0.6437(3) 0.0570(8) Uani 1.0 4 d . . .
C14 C -0.2356(3) 0.8063(2) 0.6144(3) 0.0613(8) Uani 1.0 4 d . . .
C15 C -0.2997(2) 0.8411(2) 0.5024(3) 0.0602(8) Uani 1.0 4 d . . .
C16 C -0.26229(19) 0.87666(19) 0.4138(3) 0.0553(8) Uani 1.0 4 d . . .
C17 C -0.16148(19) 0.87284(17) 0.4406(3) 0.0467(7) Uani 1.0 4 d . . .
C18 C 0.17638(18) 0.87213(18) 0.4688(3) 0.0454(7) Uani 1.0 4 d . . .
C19 C 0.21988(17) 0.79772(18) 0.4174(3) 0.0462(7) Uani 1.0 4 d . . .
C20 C 0.1745(2) 0.74369(19) 0.3127(3) 0.0542(7) Uani 1.0 4 d . . .
C21 C 0.3254(3) 0.6835(2) 0.3931(3) 0.0599(8) Uani 1.0 4 d . . .
C22 C 0.4108(3) 0.6282(3) 0.4180(4) 0.0844(11) Uani 1.0 4 d . . .
C23 C 0.4869(3) 0.6508(4) 0.5221(5) 0.0906(13) Uani 1.0 4 d . . .
C24 C 0.4811(3) 0.7238(3) 0.5993(4) 0.0835(11) Uani 1.0 4 d . . .
C25 C 0.39765(19) 0.7795(3) 0.5757(3) 0.0631(8) Uani 1.0 4 d . . .
C26 C 0.31819(17) 0.75873(18) 0.4701(3) 0.0487(7) Uani 1.0 4 d . . .
H2 H -0.3537 0.8764 -0.1278 0.0829 Uiso 1.0 4 calc R . .
H3 H -0.2094 0.8856 0.0383 0.0751 Uiso 1.0 4 calc R . .
H4 H 0.2233 0.6351 0.2385 0.0794 Uiso 1.0 4 calc R . .
H5 H -0.1626 1.1474 -0.0701 0.0627 Uiso 1.0 4 calc R . .
H6 H -0.3095 1.1414 -0.2301 0.0682 Uiso 1.0 4 calc R . .
H9 H 0.0950 0.9603 0.2485 0.0644 Uiso 1.0 4 calc R . .
H13 H -0.0969 0.7785 0.7199 0.0685 Uiso 1.0 4 calc R . .
H15 H -0.3671 0.8401 0.4881 0.0723 Uiso 1.0 4 calc R . .
H16 H -0.3027 0.9022 0.3392 0.0664 Uiso 1.0 4 calc R . .
H20 H 0.1106 0.7525 0.2602 0.0650 Uiso 1.0 4 calc R . .
H22 H 0.4154 0.5784 0.3658 0.1013 Uiso 1.0 4 calc R . .
H23 H 0.5445 0.6154 0.5410 0.1087 Uiso 1.0 4 calc R . .
H24 H 0.5346 0.7365 0.6695 0.1002 Uiso 1.0 4 calc R . .
H25 H 0.3947 0.8293 0.6288 0.0757 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Br1 C1 1.890(3) yes . .
F1 C14 1.367(5) yes . .
O1 C7 1.224(4) yes . .
O2 C18 1.225(3) yes . .
N1 C11 1.318(4) yes . .
N1 C12 1.393(4) yes . .
N2 N3 1.354(3) yes . .
N2 C11 1.404(3) yes . .
N2 C17 1.395(4) yes . .
N3 C8 1.316(4) yes . .
N4 C20 1.347(4) yes . .
N4 C21 1.386(4) yes . .
C1 C2 1.381(5) yes . .
C1 C6 1.376(4) yes . .
C2 C3 1.385(4) yes . .
C3 C4 1.390(4) yes . .
C4 C5 1.382(4) yes . .
C4 C7 1.473(4) yes . .
C5 C6 1.377(4) yes . .
C7 C8 1.502(4) yes . .
C8 C9 1.432(4) yes . .
C9 C10 1.353(4) yes . .
C10 C11 1.419(5) yes . .
C10 C18 1.514(4) yes . .
C12 C13 1.393(5) yes . .
C12 C17 1.407(4) yes . .
C13 C14 1.355(5) yes . .
C14 C15 1.395(4) yes . .
C15 C16 1.370(5) yes . .
C16 C17 1.383(4) yes . .
C18 C19 1.431(4) yes . .
C19 C20 1.381(4) yes . .
C19 C26 1.455(4) yes . .
C21 C22 1.403(5) yes . .
C21 C26 1.393(5) yes . .
C22 C23 1.364(6) yes . .
C23 C24 1.365(7) yes . .
C24 C25 1.384(5) yes . .
C25 C26 1.395(4) yes . .
N4 H4 0.860 no . .
C2 H2 0.930 no . .
C3 H3 0.930 no . .
C5 H5 0.930 no . .
C6 H6 0.930 no . .
C9 H9 0.930 no . .
C13 H13 0.930 no . .
C15 H15 0.930 no . .
C16 H16 0.930 no . .
C20 H20 0.930 no . .
C22 H22 0.930 no . .
C23 H23 0.930 no . .
C24 H24 0.930 no . .
C25 H25 0.930 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C11 N1 C12 104.6(2) yes . . .
N3 N2 C11 127.1(3) yes . . .
N3 N2 C17 126.2(2) yes . . .
C11 N2 C17 106.6(2) yes . . .
N2 N3 C8 114.2(2) yes . . .
C20 N4 C21 109.6(3) yes . . .
Br1 C1 C2 119.9(3) yes . . .
Br1 C1 C6 119.1(2) yes . . .
C2 C1 C6 121.0(3) yes . . .
C1 C2 C3 119.3(3) yes . . .
C2 C3 C4 120.5(3) yes . . .
C3 C4 C5 118.8(3) yes . . .
C3 C4 C7 122.8(3) yes . . .
C5 C4 C7 118.3(3) yes . . .
C4 C5 C6 121.2(3) yes . . .
C1 C6 C5 119.2(3) yes . . .
O1 C7 C4 121.2(3) yes . . .
O1 C7 C8 116.8(3) yes . . .
C4 C7 C8 122.0(3) yes . . .
N3 C8 C7 117.4(3) yes . . .
N3 C8 C9 123.9(3) yes . . .
C7 C8 C9 118.6(3) yes . . .
C8 C9 C10 120.5(3) yes . . .
C9 C10 C11 117.9(3) yes . . .
C9 C10 C18 123.5(3) yes . . .
C11 C10 C18 118.6(3) yes . . .
N1 C11 N2 112.8(3) yes . . .
N1 C11 C10 131.0(3) yes . . .
N2 C11 C10 116.2(3) yes . . .
N1 C12 C13 129.1(3) yes . . .
N1 C12 C17 111.6(3) yes . . .
C13 C12 C17 119.2(3) yes . . .
C12 C13 C14 116.1(3) yes . . .
F1 C14 C13 118.1(3) yes . . .
F1 C14 C15 116.6(3) yes . . .
C13 C14 C15 125.2(4) yes . . .
C14 C15 C16 119.3(3) yes . . .
C15 C16 C17 116.8(3) yes . . .
N2 C17 C12 104.3(3) yes . . .
N2 C17 C16 132.3(3) yes . . .
C12 C17 C16 123.3(3) yes . . .
O2 C18 C10 118.5(3) yes . . .
O2 C18 C19 124.3(3) yes . . .
C10 C18 C19 117.2(3) yes . . .
C18 C19 C20 126.8(3) yes . . .
C18 C19 C26 126.9(3) yes . . .
C20 C19 C26 106.1(3) yes . . .
N4 C20 C19 109.9(3) yes . . .
N4 C21 C22 130.3(3) yes . . .
N4 C21 C26 107.8(3) yes . . .
C22 C21 C26 121.9(3) yes . . .
C21 C22 C23 117.1(4) yes . . .
C22 C23 C24 121.9(4) yes . . .
C23 C24 C25 121.8(3) yes . . .
C24 C25 C26 118.1(3) yes . . .
C19 C26 C21 106.6(3) yes . . .
C19 C26 C25 134.1(3) yes . . .
C21 C26 C25 119.3(3) yes . . .
C20 N4 H4 125.205 no . . .
C21 N4 H4 125.186 no . . .
C1 C2 H2 120.369 no . . .
C3 C2 H2 120.363 no . . .
C2 C3 H3 119.770 no . . .
C4 C3 H3 119.765 no . . .
C4 C5 H5 119.390 no . . .
C6 C5 H5 119.388 no . . .
C1 C6 H6 120.398 no . . .
C5 C6 H6 120.391 no . . .
C8 C9 H9 119.748 no . . .
C10 C9 H9 119.754 no . . .
C12 C13 H13 121.933 no . . .
C14 C13 H13 121.936 no . . .
C14 C15 H15 120.372 no . . .
C16 C15 H15 120.372 no . . .
C15 C16 H16 121.578 no . . .
C17 C16 H16 121.589 no . . .
N4 C20 H20 125.033 no . . .
C19 C20 H20 125.046 no . . .
C21 C22 H22 121.444 no . . .
C23 C22 H22 121.439 no . . .
C22 C23 H23 119.033 no . . .
C24 C23 H23 119.041 no . . .
C23 C24 H24 119.116 no . . .
C25 C24 H24 119.125 no . . .
C24 C25 H25 120.968 no . . .
C26 C25 H25 120.967 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C11 N1 C12 C13 -178.9(3) no . . . .
C11 N1 C12 C17 0.5(3) no . . . .
C12 N1 C11 N2 0.4(3) no . . . .
C12 N1 C11 C10 -178.3(3) no . . . .
N3 N2 C11 N1 176.7(2) no . . . .
N3 N2 C11 C10 -4.4(4) no . . . .
C11 N2 N3 C8 1.2(4) no . . . .
N3 N2 C17 C12 -176.6(2) no . . . .
N3 N2 C17 C16 2.2(4) no . . . .
C17 N2 N3 C8 178.8(2) no . . . .
C11 N2 C17 C12 1.4(3) no . . . .
C11 N2 C17 C16 -179.8(3) no . . . .
C17 N2 C11 N1 -1.2(3) no . . . .
C17 N2 C11 C10 177.71(19) no . . . .
N2 N3 C8 C7 -174.09(18) no . . . .
N2 N3 C8 C9 2.2(4) no . . . .
C20 N4 C21 C22 178.6(3) no . . . .
C20 N4 C21 C26 -0.1(4) no . . . .
C21 N4 C20 C19 0.2(4) no . . . .
Br1 C1 C2 C3 -179.0(3) no . . . .
Br1 C1 C6 C5 -179.5(2) no . . . .
C2 C1 C6 C5 0.5(5) no . . . .
C6 C1 C2 C3 1.0(6) no . . . .
C1 C2 C3 C4 -0.9(6) no . . . .
C2 C3 C4 C5 -0.7(5) no . . . .
C2 C3 C4 C7 -177.5(3) no . . . .
C3 C4 C5 C6 2.2(5) no . . . .
C3 C4 C7 O1 155.9(3) no . . . .
C3 C4 C7 C8 -25.0(5) no . . . .
C5 C4 C7 O1 -21.0(5) no . . . .
C5 C4 C7 C8 158.1(3) no . . . .
C7 C4 C5 C6 179.2(3) no . . . .
C4 C5 C6 C1 -2.2(5) no . . . .
O1 C7 C8 N3 146.7(3) no . . . .
O1 C7 C8 C9 -29.8(4) no . . . .
C4 C7 C8 N3 -32.4(4) no . . . .
C4 C7 C8 C9 151.0(3) no . . . .
N3 C8 C9 C10 -2.4(4) no . . . .
C7 C8 C9 C10 173.9(3) no . . . .
C8 C9 C10 C11 -1.0(4) no . . . .
C8 C9 C10 C18 179.4(3) no . . . .
C9 C10 C11 N1 -177.4(3) no . . . .
C9 C10 C11 N2 3.9(4) no . . . .
C9 C10 C18 O2 112.8(4) no . . . .
C9 C10 C18 C19 -68.7(4) no . . . .
C11 C10 C18 O2 -66.8(4) no . . . .
C11 C10 C18 C19 111.7(3) no . . . .
C18 C10 C11 N1 2.2(5) no . . . .
C18 C10 C11 N2 -176.4(2) no . . . .
N1 C12 C13 C14 -179.5(3) no . . . .
N1 C12 C17 N2 -1.2(3) no . . . .
N1 C12 C17 C16 179.9(2) no . . . .
C13 C12 C17 N2 178.3(3) no . . . .
C13 C12 C17 C16 -0.7(4) no . . . .
C17 C12 C13 C14 1.2(4) no . . . .
C12 C13 C14 F1 178.5(3) no . . . .
C12 C13 C14 C15 -0.1(5) no . . . .
F1 C14 C15 C16 179.8(3) no . . . .
C13 C14 C15 C16 -1.5(5) no . . . .
C14 C15 C16 C17 1.9(4) no . . . .
C15 C16 C17 N2 -179.5(3) no . . . .
C15 C16 C17 C12 -0.9(4) no . . . .
O2 C18 C19 C20 173.4(3) no . . . .
O2 C18 C19 C26 -1.4(5) no . . . .
C10 C18 C19 C20 -5.0(5) no . . . .
C10 C18 C19 C26 -179.8(3) no . . . .
C18 C19 C20 N4 -175.8(3) no . . . .
C18 C19 C26 C21 175.7(3) no . . . .
C18 C19 C26 C25 -2.2(5) no . . . .
C20 C19 C26 C21 0.0(3) no . . . .
C20 C19 C26 C25 -177.9(3) no . . . .
C26 C19 C20 N4 -0.1(4) no . . . .
N4 C21 C22 C23 -178.1(4) no . . . .
N4 C21 C26 C19 0.1(4) no . . . .
N4 C21 C26 C25 178.3(3) no . . . .
C22 C21 C26 C19 -178.9(3) no . . . .
C22 C21 C26 C25 -0.6(5) no . . . .
C26 C21 C22 C23 0.5(6) no . . . .
C21 C22 C23 C24 -0.0(7) no . . . .
C22 C23 C24 C25 -0.4(7) no . . . .
C23 C24 C25 C26 0.3(6) no . . . .
C24 C25 C26 C19 177.9(3) no . . . .
C24 C25 C26 C21 0.1(5) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
F1 C12 3.586(4) no . .
O1 N3 3.430(4) no . .
O1 C3 3.588(4) no . .
O1 C5 2.798(3) no . .
O1 C9 2.811(4) no . .
O2 N1 3.243(4) no . .
O2 C9 3.387(3) no . .
O2 C11 3.061(4) no . .
O2 C25 3.173(4) no . .
O2 C26 3.000(4) no . .
N1 N3 3.567(3) no . .
N1 C18 3.027(4) no . .
N2 C9 2.672(4) no . .
N2 C13 3.537(4) no . .
N3 C3 3.016(4) no . .
N3 C4 2.966(4) no . .
N3 C10 2.855(4) no . .
N3 C12 3.536(4) no . .
N3 C16 3.129(5) no . .
N4 C25 3.561(4) no . .
C1 C4 2.765(4) no . .
C2 C5 2.758(5) no . .
C3 C6 2.766(4) no . .
C3 C8 3.069(4) no . .
C8 C11 2.743(4) no . .
C8 C17 3.578(5) no . .
C9 C19 3.217(4) no . .
C9 C20 3.330(4) no . .
C10 C12 3.551(5) no . .
C10 C17 3.565(5) no . .
C10 C20 2.962(5) no . .
C11 C13 3.512(5) no . .
C11 C19 3.528(4) no . .
C12 C15 2.775(5) no . .
C13 C16 2.848(4) no . .
C14 C17 2.677(5) no . .
C18 C25 3.290(4) no . .
C21 C24 2.727(5) no . .
C22 C25 2.815(6) no . .
C23 C26 2.760(5) no . .
F1 C2 3.233(4) no . 1_556
F1 C16 3.149(4) no . 4_565
F1 C17 3.381(4) no . 4_565
F1 C24 3.363(4) no . 1_455
O1 O1 3.266(4) no . 3_575
O1 C4 3.487(4) no . 3_575
O1 C7 3.298(5) no . 3_575
O1 C13 3.455(4) no . 3_576
O2 N2 3.281(3) no . 3_576
O2 N3 3.292(4) no . 3_576
O2 N4 2.809(4) no . 4_565
O2 C16 3.026(4) no . 3_576
O2 C17 3.115(4) no . 3_576
N1 C8 3.592(4) no . 3_576
N1 C20 3.386(4) no . 4_565
N2 O2 3.281(3) no . 3_576
N3 O2 3.292(4) no . 3_576
N3 N4 3.558(4) no . 2_555
N4 O2 2.809(4) no . 4_564
N4 N3 3.558(4) no . 2_545
N4 C4 3.491(5) no . 2_545
N4 C5 3.568(5) no . 2_545
N4 C7 3.542(5) no . 2_545
N4 C18 3.598(4) no . 4_564
C2 F1 3.233(4) no . 1_554
C4 O1 3.487(4) no . 3_575
C4 N4 3.491(5) no . 2_555
C5 N4 3.568(5) no . 2_555
C5 C19 3.460(4) no . 2_555
C5 C20 3.599(4) no . 2_555
C5 C20 3.594(5) no . 3_575
C5 C21 3.401(5) no . 2_555
C5 C26 3.322(4) no . 2_555
C6 C19 3.541(5) no . 3_575
C6 C20 3.481(5) no . 3_575
C6 C25 3.461(5) no . 2_555
C6 C26 3.446(5) no . 2_555
C7 O1 3.298(5) no . 3_575
C7 N4 3.542(5) no . 2_555
C8 N1 3.592(4) no . 3_576
C9 C12 3.537(4) no . 3_576
C11 C11 3.568(4) no . 3_576
C12 C9 3.537(4) no . 3_576
C13 O1 3.455(4) no . 3_576
C16 F1 3.149(4) no . 4_564
C16 O2 3.026(4) no . 3_576
C17 F1 3.381(4) no . 4_564
C17 O2 3.115(4) no . 3_576
C18 N4 3.598(4) no . 4_565
C19 C5 3.460(4) no . 2_545
C19 C6 3.541(5) no . 3_575
C20 N1 3.386(4) no . 4_564
C20 C5 3.599(4) no . 2_545
C20 C5 3.594(5) no . 3_575
C20 C6 3.481(5) no . 3_575
C21 C5 3.401(5) no . 2_545
C24 F1 3.363(4) no . 1_655
C25 C6 3.461(5) no . 2_545
C26 C5 3.322(4) no . 2_545
C26 C6 3.446(5) no . 2_545
Br1 H2 2.9164 no . .
Br1 H6 2.8927 no . .
F1 H13 2.5261 no . .
F1 H15 2.5140 no . .
O1 H5 2.5161 no . .
O1 H9 2.5871 no . .
O2 H9 3.5366 no . .
O2 H25 2.6882 no . .
N1 H13 2.7795 no . .
N2 H16 2.8203 no . .
N3 H3 2.5725 no . .
N3 H9 3.2423 no . .
N3 H16 2.9867 no . .
N4 H22 2.7968 no . .
C1 H3 3.2259 no . .
C1 H5 3.2118 no . .
C2 H6 3.2379 no . .
C3 H5 3.2256 no . .
C4 H2 3.2488 no . .
C4 H6 3.2414 no . .
C5 H3 3.2268 no . .
C6 H2 3.2370 no . .
C7 H3 2.6852 no . .
C7 H5 2.5829 no . .
C7 H9 2.6645 no . .
C8 H3 2.7720 no . .
C9 H20 2.8949 no . .
C10 H20 2.7409 no . .
C11 H9 3.2229 no . .
C11 H20 3.5466 no . .
C12 H16 3.2957 no . .
C13 H15 3.2635 no . .
C14 H16 3.2377 no . .
C15 H13 3.2791 no . .
C17 H13 3.2687 no . .
C17 H15 3.1971 no . .
C18 H9 2.6895 no . .
C18 H20 2.8004 no . .
C18 H25 3.1412 no . .
C19 H4 3.0587 no . .
C19 H9 3.1465 no . .
C19 H25 2.8973 no . .
C20 H9 3.2511 no . .
C21 H20 3.1271 no . .
C21 H23 3.2058 no . .
C21 H25 3.2519 no . .
C22 H4 2.8129 no . .
C22 H24 3.2140 no . .
C23 H25 3.2402 no . .
C24 H22 3.2285 no . .
C25 H23 3.2309 no . .
C26 H4 3.0733 no . .
C26 H20 3.1674 no . .
C26 H22 3.2843 no . .
C26 H24 3.2235 no . .
H2 H3 2.3167 no . .
H4 H20 2.3775 no . .
H4 H22 2.7929 no . .
H5 H6 2.3038 no . .
H9 H20 2.9279 no . .
H15 H16 2.3273 no . .
H22 H23 2.3007 no . .
H23 H24 2.2693 no . .
H24 H25 2.3154 no . .
Br1 H15 3.3495 no . 3_475
Br1 H16 3.5672 no . 3_475
Br1 H22 3.3847 no . 4_464
Br1 H25 3.1145 no . 1_454
F1 H2 2.9185 no . 1_556
F1 H3 3.2030 no . 4_565
F1 H16 2.9939 no . 4_565
F1 H23 3.4203 no . 1_455
F1 H24 2.6641 no . 1_455
O1 H13 2.9319 no . 3_576
O1 H20 3.4252 no . 2_555
O2 H4 2.0101 no . 4_565
O2 H16 2.9287 no . 3_576
N1 H4 3.2345 no . 4_565
N1 H5 3.5499 no . 2_545
N1 H20 2.6855 no . 4_565
N2 H13 3.0854 no . 4_564
N3 H4 2.9845 no . 2_555
N3 H13 3.2509 no . 4_564
N4 H5 3.5745 no . 2_545
N4 H5 3.4842 no . 3_575
N4 H6 2.9569 no . 3_575
N4 H25 3.3951 no . 4_564
C2 H23 3.1264 no . 4_464
C3 H23 3.5836 no . 4_464
C4 H9 3.3583 no . 3_575
C5 H9 2.8934 no . 3_575
C5 H20 3.4941 no . 3_575
C6 H9 3.2131 no . 3_575
C7 H4 3.5075 no . 2_555
C8 H4 3.5120 no . 2_555
C8 H13 3.5282 no . 4_564
C9 H5 3.5807 no . 3_575
C11 H13 3.3459 no . 4_564
C12 H3 3.4826 no . 4_565
C12 H20 3.3960 no . 4_565
C13 H3 2.9483 no . 4_565
C13 H9 3.5347 no . 3_576
C13 H20 3.4606 no . 4_565
C14 H3 2.8895 no . 4_565
C15 H2 3.3727 no . 4_565
C15 H3 3.4145 no . 4_565
C18 H4 2.8999 no . 4_565
C18 H5 3.3852 no . 2_545
C19 H5 3.0000 no . 2_545
C19 H6 2.9258 no . 3_575
C20 H5 3.2551 no . 2_545
C20 H5 3.0914 no . 3_575
C20 H6 2.8928 no . 3_575
C21 H5 3.5582 no . 2_545
C21 H6 3.0351 no . 3_575
C21 H25 3.4309 no . 4_564
C22 H2 3.5788 no . 4_665
C22 H23 3.4865 no . 3_666
C22 H25 3.2499 no . 4_564
C23 H2 3.2680 no . 4_665
C23 H15 3.4821 no . 1_655
C23 H22 3.5801 no . 3_666
C24 H6 3.4479 no . 2_545
C24 H15 3.2741 no . 1_655
C25 H6 3.1288 no . 2_545
C26 H5 3.2105 no . 2_545
C26 H6 3.3997 no . 2_545
C26 H6 3.0145 no . 3_575
H2 F1 2.9185 no . 1_554
H2 C15 3.3727 no . 4_564
H2 C22 3.5788 no . 4_464
H2 C23 3.2680 no . 4_464
H2 H15 3.3408 no . 4_564
H2 H22 3.3547 no . 4_464
H2 H23 2.7437 no . 4_464
H2 H24 3.0562 no . 1_454
H3 F1 3.2030 no . 4_564
H3 C12 3.4826 no . 4_564
H3 C13 2.9483 no . 4_564
H3 C14 2.8895 no . 4_564
H3 C15 3.4145 no . 4_564
H3 H13 3.1663 no . 4_564
H3 H23 3.5449 no . 4_464
H4 O2 2.0101 no . 4_564
H4 N1 3.2345 no . 4_564
H4 N3 2.9845 no . 2_545
H4 C7 3.5075 no . 2_545
H4 C8 3.5120 no . 2_545
H4 C18 2.8999 no . 4_564
H4 H5 3.5583 no . 3_575
H4 H6 3.3877 no . 3_575
H4 H25 3.1247 no . 4_564
H5 N1 3.5499 no . 2_555
H5 N4 3.5745 no . 2_555
H5 N4 3.4842 no . 3_575
H5 C9 3.5807 no . 3_575
H5 C18 3.3852 no . 2_555
H5 C19 3.0000 no . 2_555
H5 C20 3.2551 no . 2_555
H5 C20 3.0914 no . 3_575
H5 C21 3.5582 no . 2_555
H5 C26 3.2105 no . 2_555
H5 H4 3.5583 no . 3_575
H5 H9 2.9177 no . 3_575
H5 H20 2.8534 no . 3_575
H6 N4 2.9569 no . 3_575
H6 C19 2.9258 no . 3_575
H6 C20 2.8928 no . 3_575
H6 C21 3.0351 no . 3_575
H6 C24 3.4479 no . 2_555
H6 C25 3.1288 no . 2_555
H6 C26 3.3997 no . 2_555
H6 C26 3.0145 no . 3_575
H6 H4 3.3877 no . 3_575
H6 H9 3.4614 no . 3_575
H6 H20 3.3325 no . 3_575
H6 H25 3.2634 no . 2_555
H9 C4 3.3583 no . 3_575
H9 C5 2.8934 no . 3_575
H9 C6 3.2131 no . 3_575
H9 C13 3.5347 no . 3_576
H9 H5 2.9177 no . 3_575
H9 H6 3.4614 no . 3_575
H13 O1 2.9319 no . 3_576
H13 N2 3.0854 no . 4_565
H13 N3 3.2509 no . 4_565
H13 C8 3.5282 no . 4_565
H13 C11 3.3459 no . 4_565
H13 H3 3.1663 no . 4_565
H13 H20 2.9025 no . 4_565
H15 Br1 3.3495 no . 3_475
H15 C23 3.4821 no . 1_455
H15 C24 3.2741 no . 1_455
H15 H2 3.3408 no . 4_565
H15 H23 3.5241 no . 1_455
H15 H24 3.1815 no . 1_455
H15 H24 3.5840 no . 4_464
H16 Br1 3.5672 no . 3_475
H16 F1 2.9939 no . 4_564
H16 O2 2.9287 no . 3_576
H16 H22 3.4241 no . 2_555
H16 H23 3.3929 no . 4_464
H16 H24 3.1764 no . 4_464
H20 O1 3.4252 no . 2_545
H20 N1 2.6855 no . 4_564
H20 C5 3.4941 no . 3_575
H20 C12 3.3960 no . 4_564
H20 C13 3.4606 no . 4_564
H20 H5 2.8534 no . 3_575
H20 H6 3.3325 no . 3_575
H20 H13 2.9025 no . 4_564
H22 Br1 3.3847 no . 4_665
H22 C23 3.5801 no . 3_666
H22 H2 3.3547 no . 4_665
H22 H16 3.4241 no . 2_545
H22 H23 2.9098 no . 3_666
H22 H25 2.9000 no . 4_564
H23 F1 3.4203 no . 1_655
H23 C2 3.1264 no . 4_665
H23 C3 3.5836 no . 4_665
H23 C22 3.4865 no . 3_666
H23 H2 2.7437 no . 4_665
H23 H3 3.5449 no . 4_665
H23 H15 3.5241 no . 1_655
H23 H16 3.3929 no . 4_665
H23 H22 2.9098 no . 3_666
H23 H23 3.5001 no . 3_666
H24 F1 2.6641 no . 1_655
H24 H2 3.0562 no . 1_656
H24 H15 3.1815 no . 1_655
H24 H15 3.5840 no . 4_665
H24 H16 3.1764 no . 4_665
H25 Br1 3.1145 no . 1_656
H25 N4 3.3951 no . 4_565
H25 C21 3.4309 no . 4_565
H25 C22 3.2499 no . 4_565
H25 H4 3.1247 no . 4_565
H25 H6 3.2634 no . 2_545
H25 H22 2.9000 no . 4_565

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N4 H4 O2 . . 4_564 2.809(4) 0.860 2.010 154.1 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        4y
####################################################################### 
# 
# 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_4u
_database_code_depnum_ccdc_archive 'CCDC 1420059'
_audit_update_record             
;
2015-09-17 deposited with the CCDC.
2015-10-14 downloaded from the CCDC.
;
_chemical_name_systematic        4u
_chemical_name_common            Hamada_FK113_18_02_15
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H19 Br N4 O5 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         579.42

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6551(11)
_cell_length_b                   14.067(2)
_cell_length_c                   14.367(2)
_cell_angle_alpha                106.520(11)
_cell_angle_beta                 100.524(12)
_cell_angle_gamma                98.459(11)
_cell_volume                     1239.2(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5258
_cell_measurement_theta_min      5.4117
_cell_measurement_theta_max      66.0963
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             588

_exptl_absorpt_coefficient_mu    3.443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_T_max  0.90

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
__diffrn_source_type             'Incoatec Cu-ImS'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'mirror optics'

_diffrn_measurement_device_type  'Bruker X8 Prospector'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            13406
_diffrn_reflns_av_R_equivalents  0.0894
_diffrn_reflns_av_unetI/netI     0.1150
_diffrn_reflns_theta_min         5.41
_diffrn_reflns_theta_max         66.74
_diffrn_reflns_theta_full        66.74
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16

_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.
;

_reflns_number_total             4277
_reflns_number_gt                2916
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.1698
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_refine_ls_number_reflns         4277
_refine_ls_number_parameters     336
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1181P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.580
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2012.4.0.0'
_computing_cell_refinement       'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 3.1'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 1.77177(8) 0.36839(4) -0.01653(4) 0.0944(3) Uani d . 1 . .
S S1 0.0340(2) 0.00359(9) 0.83711(8) 0.0825(4) Uani d . 1 . .
O O4 0.7570(4) 0.29755(17) 0.57103(18) 0.0564(6) Uani d . 1 . .
O O1 1.3855(3) 0.18884(16) 0.32003(19) 0.0513(6) Uani d . 1 . .
C C22 0.7114(5) -0.0734(3) 0.4577(3) 0.0572(10) Uani d . 1 . .
H H22 0.689 -0.1426 0.4489 0.069 Uiso calc R 1 . .
C C21 0.6976(5) -0.0401(2) 0.3753(3) 0.0535(9) Uani d . 1 . .
H H21 0.6636 -0.0868 0.3114 0.064 Uiso calc R 1 . .
C C20 0.7340(4) 0.0622(2) 0.3880(2) 0.0438(7) Uani d . 1 . .
H H20 0.7279 0.0845 0.3327 0.053 Uiso calc R 1 . .
C C19 0.7798(4) 0.1320(2) 0.4834(2) 0.0381(6) Uani d . 1 . .
C C18 0.8071(4) 0.2424(2) 0.5015(2) 0.0391(7) Uani d . 1 . .
C C10 0.9042(4) 0.28679(19) 0.4328(2) 0.0355(6) Uani d . 1 . .
C C9 1.0553(4) 0.25003(19) 0.3899(2) 0.0369(6) Uani d . 1 . .
H H9 1.0967 0.1932 0.4014 0.044 Uiso calc R 1 . .
C C8 1.1524(4) 0.29605(19) 0.3278(2) 0.0346(6) Uani d . 1 . .
C C7 1.3215(4) 0.25130(19) 0.2854(2) 0.0377(6) Uani d . 1 . .
C C4 1.4120(4) 0.2795(2) 0.2069(2) 0.0365(6) Uani d . 1 . .
C C3 1.5806(4) 0.2370(2) 0.1830(2) 0.0418(7) Uani d . 1 . .
H H3 1.6242 0.191 0.2134 0.05 Uiso calc R 1 . .
C C2 1.6830(5) 0.2616(2) 0.1157(3) 0.0504(8) Uani d . 1 . .
H H2 1.7948 0.2325 0.1008 0.061 Uiso calc R 1 . .
C C5 1.3472(5) 0.3455(2) 0.1574(3) 0.0511(8) Uani d . 1 . .
H H5 1.233 0.3735 0.1704 0.061 Uiso calc R 1 . .
C C6 1.4492(6) 0.3702(3) 0.0898(3) 0.0589(9) Uani d . 1 . .
H H6 1.4036 0.4142 0.0571 0.071 Uiso calc R 1 . .
N N3 1.1023(3) 0.37562(16) 0.30711(18) 0.0348(5) Uani d . 1 . .
N N2 0.9513(3) 0.41083(15) 0.34890(17) 0.0333(5) Uani d . 1 . .
C C11 0.8461(4) 0.37336(19) 0.4116(2) 0.0343(6) Uani d . 1 . .
N N1 0.7019(4) 0.42463(16) 0.43664(18) 0.0375(6) Uani d . 1 . .
C C12 0.7086(4) 0.49516(19) 0.3869(2) 0.0368(6) Uani d . 1 . .
C C17 0.8608(4) 0.48830(18) 0.3308(2) 0.0348(6) Uani d . 1 . .
C C16 0.8976(5) 0.5477(2) 0.2723(2) 0.0427(7) Uani d . 1 . .
H H16 1.0005 0.5423 0.2363 0.051 Uiso calc R 1 . .
C C15 0.7692(5) 0.6159(2) 0.2713(2) 0.0441(7) Uani d . 1 . .
C C14 0.6126(5) 0.6255(2) 0.3248(2) 0.0467(8) Uani d . 1 . .
H H14 0.5297 0.6726 0.3204 0.056 Uiso calc R 1 . .
C C13 0.5814(5) 0.5655(2) 0.3837(2) 0.0435(7) Uani d . 1 . .
H H13 0.4793 0.5715 0.4201 0.052 Uiso calc R 1 . .
N N4 0.7998(5) 0.6824(2) 0.2109(2) 0.0608(8) Uani d . 1 . .
O O3 0.9322(7) 0.6755(3) 0.1646(3) 0.1250(16) Uani d . 1 . .
O O2 0.6901(5) 0.7437(2) 0.2098(2) 0.0909(10) Uani d . 1 . .
C C23 0.7581(5) -0.0049(3) 0.5522(3) 0.0550(9) Uani d . 1 . .
H H23 0.768 -0.0278 0.6072 0.066 Uiso calc R 1 . .
C C24 0.7902(4) 0.0968(2) 0.5658(3) 0.0449(7) Uani d . 1 . .
H H24 0.8191 0.1428 0.6299 0.054 Uiso calc R 1 . .
C C26 -0.1873(10) 0.0507(4) 0.8645(5) 0.126(2) Uani d . 1 . .
H H26A -0.3114 -0.0005 0.8295 0.189 Uiso calc R 1 . .
H H26B -0.1937 0.1096 0.8438 0.189 Uiso calc R 1 . .
H H26C -0.1772 0.0687 0.9351 0.189 Uiso calc R 1 . .
C C25 0.2281(11) 0.0997(4) 0.9316(5) 0.145(3) Uani d . 1 . .
H H25A 0.1879 0.1117 0.9941 0.218 Uiso calc R 1 . .
H H25B 0.2424 0.161 0.9143 0.218 Uiso calc R 1 . .
H H25C 0.3591 0.0784 0.9375 0.218 Uiso calc R 1 . .
O O5 0.0275(5) -0.0889(2) 0.8658(3) 0.0952(11) Uani d . 1 . .
C C1 1.6189(5) 0.3296(3) 0.0705(3) 0.0540(8) Uani d . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C1 . 1.894(4) ?
S1 O5 . 1.469(3) ?
S1 C26 . 1.765(6) ?
S1 C25 . 1.772(5) ?
O4 C18 . 1.211(4) ?
O1 C7 . 1.217(3) ?
C22 C23 . 1.372(6) ?
C22 C21 . 1.384(5) ?
C22 H22 . 0.93 ?
C21 C20 . 1.376(4) ?
C21 H21 . 0.93 ?
C20 C19 . 1.390(4) ?
C20 H20 . 0.93 ?
C19 C24 . 1.401(4) ?
C19 C18 . 1.478(4) ?
C18 C10 . 1.499(4) ?
C10 C9 . 1.362(4) ?
C10 C11 . 1.425(4) ?
C9 C8 . 1.431(4) ?
C9 H9 . 0.93 ?
C8 N3 . 1.310(3) ?
C8 C7 . 1.508(4) ?
C7 C4 . 1.492(4) ?
C4 C5 . 1.390(4) ?
C4 C3 . 1.399(4) ?
C3 C2 . 1.371(5) ?
C3 H3 . 0.93 ?
C2 C1 . 1.375(5) ?
C2 H2 . 0.93 ?
C5 C6 . 1.374(5) ?
C5 H5 . 0.93 ?
C6 C1 . 1.375(5) ?
C6 H6 . 0.93 ?
N3 N2 . 1.347(3) ?
N2 C17 . 1.384(3) ?
N2 C11 . 1.404(4) ?
C11 N1 . 1.324(3) ?
N1 C12 . 1.378(4) ?
C12 C13 . 1.399(4) ?
C12 C17 . 1.402(4) ?
C17 C16 . 1.371(4) ?
C16 C15 . 1.378(4) ?
C16 H16 . 0.93 ?
C15 C14 . 1.403(4) ?
C15 N4 . 1.462(4) ?
C14 C13 . 1.375(4) ?
C14 H14 . 0.93 ?
C13 H13 . 0.93 ?
N4 O3 . 1.196(4) ?
N4 O2 . 1.211(4) ?
C23 C24 . 1.367(4) ?
C23 H23 . 0.93 ?
C24 H24 . 0.93 ?
C26 H26A . 0.96 ?
C26 H26B . 0.96 ?
C26 H26C . 0.96 ?
C25 H25A . 0.96 ?
C25 H25B . 0.96 ?
C25 H25C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O5 S1 C26 . . 106.4(3) ?
O5 S1 C25 . . 106.5(3) ?
C26 S1 C25 . . 98.1(4) ?
C23 C22 C21 . . 120.3(3) ?
C23 C22 H22 . . 119.9 ?
C21 C22 H22 . . 119.9 ?
C20 C21 C22 . . 120.1(3) ?
C20 C21 H21 . . 119.9 ?
C22 C21 H21 . . 119.9 ?
C21 C20 C19 . . 119.9(3) ?
C21 C20 H20 . . 120.0 ?
C19 C20 H20 . . 120.0 ?
C20 C19 C24 . . 119.2(3) ?
C20 C19 C18 . . 122.5(3) ?
C24 C19 C18 . . 118.3(3) ?
O4 C18 C19 . . 121.8(3) ?
O4 C18 C10 . . 119.7(3) ?
C19 C18 C10 . . 118.5(2) ?
C9 C10 C11 . . 116.3(3) ?
C9 C10 C18 . . 122.9(2) ?
C11 C10 C18 . . 120.8(2) ?
C10 C9 C8 . . 122.1(2) ?
C10 C9 H9 . . 119.0 ?
C8 C9 H9 . . 119.0 ?
N3 C8 C9 . . 123.0(2) ?
N3 C8 C7 . . 118.7(3) ?
C9 C8 C7 . . 118.3(2) ?
O1 C7 C4 . . 119.9(2) ?
O1 C7 C8 . . 115.7(3) ?
C4 C7 C8 . . 124.4(2) ?
C5 C4 C3 . . 117.5(3) ?
C5 C4 C7 . . 126.1(2) ?
C3 C4 C7 . . 116.4(3) ?
C2 C3 C4 . . 121.5(3) ?
C2 C3 H3 . . 119.2 ?
C4 C3 H3 . . 119.2 ?
C3 C2 C1 . . 119.4(3) ?
C3 C2 H2 . . 120.3 ?
C1 C2 H2 . . 120.3 ?
C6 C5 C4 . . 121.1(3) ?
C6 C5 H5 . . 119.4 ?
C4 C5 H5 . . 119.4 ?
C5 C6 C1 . . 119.9(3) ?
C5 C6 H6 . . 120.1 ?
C1 C6 H6 . . 120.1 ?
C8 N3 N2 . . 114.6(2) ?
N3 N2 C17 . . 124.8(2) ?
N3 N2 C11 . . 127.9(2) ?
C17 N2 C11 . . 107.2(2) ?
N1 C11 N2 . . 111.7(2) ?
N1 C11 C10 . . 132.0(3) ?
N2 C11 C10 . . 116.2(2) ?
C11 N1 C12 . . 104.8(2) ?
N1 C12 C13 . . 128.4(3) ?
N1 C12 C17 . . 112.0(2) ?
C13 C12 C17 . . 119.5(3) ?
C16 C17 N2 . . 131.5(2) ?
C16 C17 C12 . . 124.3(2) ?
N2 C17 C12 . . 104.2(2) ?
C17 C16 C15 . . 114.3(3) ?
C17 C16 H16 . . 122.9 ?
C15 C16 H16 . . 122.9 ?
C16 C15 C14 . . 124.0(3) ?
C16 C15 N4 . . 117.5(3) ?
C14 C15 N4 . . 118.5(3) ?
C13 C14 C15 . . 120.1(3) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C14 C13 C12 . . 117.7(3) ?
C14 C13 H13 . . 121.1 ?
C12 C13 H13 . . 121.1 ?
O3 N4 O2 . . 121.7(3) ?
O3 N4 C15 . . 119.6(3) ?
O2 N4 C15 . . 118.6(3) ?
C24 C23 C22 . . 120.3(3) ?
C24 C23 H23 . . 119.9 ?
C22 C23 H23 . . 119.9 ?
C23 C24 C19 . . 120.2(3) ?
C23 C24 H24 . . 119.9 ?
C19 C24 H24 . . 119.9 ?
S1 C26 H26A . . 109.5 ?
S1 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
S1 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
S1 C25 H25A . . 109.5 ?
S1 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
S1 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
C6 C1 C2 . . 120.5(3) ?
C6 C1 Br1 . . 120.7(3) ?
C2 C1 Br1 . . 118.8(2) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C23 C22 C21 C20 . . . . 1.1(5) ?
C22 C21 C20 C19 . . . . -1.6(4) ?
C21 C20 C19 C24 . . . . 0.6(4) ?
C21 C20 C19 C18 . . . . -176.0(3) ?
C20 C19 C18 O4 . . . . 147.1(3) ?
C24 C19 C18 O4 . . . . -29.6(4) ?
C20 C19 C18 C10 . . . . -34.4(4) ?
C24 C19 C18 C10 . . . . 149.0(3) ?
O4 C18 C10 C9 . . . . 145.0(3) ?
C19 C18 C10 C9 . . . . -33.6(4) ?
O4 C18 C10 C11 . . . . -32.9(4) ?
C19 C18 C10 C11 . . . . 148.6(3) ?
C11 C10 C9 C8 . . . . 0.6(4) ?
C18 C10 C9 C8 . . . . -177.3(3) ?
C10 C9 C8 N3 . . . . -0.6(4) ?
C10 C9 C8 C7 . . . . 178.7(3) ?
N3 C8 C7 O1 . . . . 168.3(3) ?
C9 C8 C7 O1 . . . . -11.1(4) ?
N3 C8 C7 C4 . . . . -11.2(4) ?
C9 C8 C7 C4 . . . . 169.5(2) ?
O1 C7 C4 C5 . . . . 176.6(3) ?
C8 C7 C4 C5 . . . . -4.0(5) ?
O1 C7 C4 C3 . . . . -5.0(4) ?
C8 C7 C4 C3 . . . . 174.4(2) ?
C5 C4 C3 C2 . . . . 2.0(4) ?
C7 C4 C3 C2 . . . . -176.6(3) ?
C4 C3 C2 C1 . . . . 0.0(5) ?
C3 C4 C5 C6 . . . . -1.8(5) ?
C7 C4 C5 C6 . . . . 176.6(3) ?
C4 C5 C6 C1 . . . . -0.3(6) ?
C9 C8 N3 N2 . . . . -0.1(4) ?
C7 C8 N3 N2 . . . . -179.4(2) ?
C8 N3 N2 C17 . . . . -174.2(2) ?
C8 N3 N2 C11 . . . . 0.9(4) ?
N3 N2 C11 N1 . . . . -178.1(2) ?
C17 N2 C11 N1 . . . . -2.3(3) ?
N3 N2 C11 C10 . . . . -0.8(4) ?
C17 N2 C11 C10 . . . . 174.9(2) ?
C9 C10 C11 N1 . . . . 176.6(3) ?
C18 C10 C11 N1 . . . . -5.4(5) ?
C9 C10 C11 N2 . . . . 0.1(4) ?
C18 C10 C11 N2 . . . . 178.0(2) ?
N2 C11 N1 C12 . . . . 1.7(3) ?
C10 C11 N1 C12 . . . . -174.9(3) ?
C11 N1 C12 C13 . . . . 176.7(3) ?
C11 N1 C12 C17 . . . . -0.6(3) ?
N3 N2 C17 C16 . . . . -1.4(5) ?
C11 N2 C17 C16 . . . . -177.3(3) ?
N3 N2 C17 C12 . . . . 177.7(2) ?
C11 N2 C17 C12 . . . . 1.7(3) ?
N1 C12 C17 C16 . . . . 178.4(3) ?
C13 C12 C17 C16 . . . . 0.8(4) ?
N1 C12 C17 N2 . . . . -0.8(3) ?
C13 C12 C17 N2 . . . . -178.3(3) ?
N2 C17 C16 C15 . . . . 178.2(3) ?
C12 C17 C16 C15 . . . . -0.7(4) ?
C17 C16 C15 C14 . . . . -0.1(5) ?
C17 C16 C15 N4 . . . . 179.7(3) ?
C16 C15 C14 C13 . . . . 0.8(5) ?
N4 C15 C14 C13 . . . . -178.9(3) ?
C15 C14 C13 C12 . . . . -0.7(5) ?
N1 C12 C13 C14 . . . . -177.2(3) ?
C17 C12 C13 C14 . . . . 0.0(4) ?
C16 C15 N4 O3 . . . . 0.3(5) ?
C14 C15 N4 O3 . . . . -179.9(4) ?
C16 C15 N4 O2 . . . . -179.3(3) ?
C14 C15 N4 O2 . . . . 0.5(5) ?
C21 C22 C23 C24 . . . . 0.4(5) ?
C22 C23 C24 C19 . . . . -1.3(4) ?
C20 C19 C24 C23 . . . . 0.8(4) ?
C18 C19 C24 C23 . . . . 177.6(2) ?
C5 C6 C1 C2 . . . . 2.4(6) ?
C5 C6 C1 Br1 . . . . -176.3(3) ?
C3 C2 C1 C6 . . . . -2.2(5) ?
C3 C2 C1 Br1 . . . . 176.5(2) ?

####################################################################### 
# 
# 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_4g
_database_code_depnum_ccdc_archive 'CCDC 1425379'
_audit_update_record             
;
2015-09-17 deposited with the CCDC.
2015-10-14 downloaded from the CCDC.
;
_chemical_name_systematic        4g
_chemical_name_common            Hamada_FK130C_23_03_15
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H16 N4 O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         452.42

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.2274(4)
_cell_length_b                   7.0898(2)
_cell_length_c                   21.0075(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.677(2)
_cell_angle_gamma                90
_cell_volume                     2100.02(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7101
_cell_measurement_theta_min      4.0146
_cell_measurement_theta_max      66.0109
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936

_exptl_absorpt_coefficient_mu    0.851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              'Incoatec Cu-ImS'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'mirror optics'

_diffrn_measurement_device_type  'Bruker X8 Prospector'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            11406
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_theta_min         4.93
_diffrn_reflns_theta_max         66.15
_diffrn_reflns_theta_full        66.15
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 0.945
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       20

_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.
;

_reflns_number_total             3477
_reflns_number_gt                2807
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1569
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_number_reflns         3477
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0590P)²+1.6545P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.291
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2012.4.0.0'
_computing_cell_refinement       'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury 3.1'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O5 0.42408(14) 0.2051(3) 1.07656(9) 0.0620(6) Uani d . 1 . .
O O4 0.45818(14) 0.4442(3) 0.79118(9) 0.0644(6) Uani d . 1 . .
N N1 0.86551(15) 0.1984(4) 0.75687(11) 0.0528(6) Uani d . 1 . .
O O3 0.7914(2) -0.4763(4) 0.93132(15) 0.1033(10) Uani d . 1 . .
O O1 0.76146(17) 0.7368(3) 0.71232(10) 0.0704(6) Uani d . 1 . .
N N3 0.74140(14) 0.1561(3) 0.81167(9) 0.0428(5) Uani d . 1 . .
C C20 0.56831(17) 0.2871(4) 0.94745(12) 0.0459(6) Uani d . 1 . .
H H20 0.6315 0.2885 0.9404 0.055 Uiso calc R 1 . .
C C17 0.64879(18) 0.4643(4) 0.76775(12) 0.0478(6) Uani d . 1 . .
H H17 0.6138 0.571 0.754 0.057 Uiso calc R 1 . .
C C9 0.78343(17) 0.2665(4) 0.76808(12) 0.0465(6) Uani d . 1 . .
O O2 0.9282(2) -0.5545(5) 0.91162(18) 0.1304(13) Uani d . 1 . .
N N2 0.8624(2) -0.4465(4) 0.90742(13) 0.0704(7) Uani d . 1 . .
C C13 0.8677(2) -0.2739(4) 0.86936(13) 0.0531(7) Uani d . 1 . .
C C14 0.79373(19) -0.1484(4) 0.86696(12) 0.0483(6) Uani d . 1 . .
H H14 0.7425 -0.1661 0.8896 0.058 Uiso calc R 1 . .
C C15 0.80189(17) 0.0063(4) 0.82819(11) 0.0428(6) Uani d . 1 . .
N N4 0.65847(14) 0.1873(3) 0.83401(9) 0.0439(5) Uani d . 1 . .
C C16 0.61413(18) 0.3403(4) 0.81193(11) 0.0435(6) Uani d . 1 . .
C C18 0.51785(18) 0.3752(4) 0.83206(12) 0.0452(6) Uani d . 1 . .
C C19 0.49790(17) 0.3283(4) 0.89685(12) 0.0424(6) Uani d . 1 . .
C C24 0.40369(18) 0.3279(4) 0.90910(13) 0.0486(6) Uani d . 1 . .
H H24 0.3555 0.3574 0.8762 0.058 Uiso calc R 1 . .
C C23 0.38123(18) 0.2846(4) 0.96895(13) 0.0522(7) Uani d . 1 . .
H H23 0.3182 0.2826 0.9762 0.063 Uiso calc R 1 . .
C C22 0.45315(19) 0.2435(4) 1.01892(13) 0.0475(6) Uani d . 1 . .
C C25 0.4957(2) 0.1572(5) 1.12849(14) 0.0627(8) Uani d . 1 . .
H H25A 0.5289 0.0466 1.1175 0.094 Uiso calc R 1 . .
H H25B 0.4666 0.1328 1.1664 0.094 Uiso calc R 1 . .
H H25C 0.5395 0.26 1.1365 0.094 Uiso calc R 1 . .
C C21 0.54649(18) 0.2444(4) 1.00782(12) 0.0474(6) Uani d . 1 . .
H H21 0.5946 0.2162 1.0409 0.057 Uiso calc R 1 . .
C C8 0.73200(18) 0.4308(4) 0.74505(11) 0.0466(6) Uani d . 1 . .
C C10 0.87796(17) 0.0364(4) 0.79366(12) 0.0477(6) Uani d . 1 . .
C C12 0.9456(2) -0.2499(5) 0.83632(14) 0.0589(8) Uani d . 1 . .
H H12 0.9939 -0.3394 0.8403 0.071 Uiso calc R 1 . .
C C11 0.95125(19) -0.0952(5) 0.79811(14) 0.0597(8) Uani d . 1 . .
H H11 1.0027 -0.0783 0.7757 0.072 Uiso calc R 1 . .
C C7 0.76892(19) 0.5701(5) 0.69994(12) 0.0518(7) Uani d . 1 . .
C C4 0.80586(18) 0.5068(5) 0.64117(12) 0.0554(8) Uani d . 1 . .
C C5 0.8579(2) 0.6339(6) 0.60943(16) 0.0760(10) Uani d . 1 . .
H H5 0.8716 0.7533 0.6265 0.091 Uiso calc R 1 . .
C C6 0.8891(3) 0.5821(9) 0.5525(2) 0.0984(15) Uani d . 1 . .
H H6 0.9247 0.6661 0.5315 0.118 Uiso calc R 1 . .
C C1 0.8678(3) 0.4070(9) 0.52676(19) 0.1046(16) Uani d . 1 . .
H H1 0.8881 0.3738 0.488 0.126 Uiso calc R 1 . .
C C2 0.8169(3) 0.2809(7) 0.55752(17) 0.0885(12) Uani d . 1 . .
H H2 0.803 0.1622 0.5399 0.106 Uiso calc R 1 . .
C C3 0.7860(2) 0.3306(6) 0.61515(14) 0.0671(9) Uani d . 1 . .
H H3 0.7517 0.2446 0.6363 0.081 Uiso calc R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O5 C22 . 1.358(3) ?
O5 C25 . 1.430(4) ?
O4 C18 . 1.226(3) ?
N1 C9 . 1.314(3) ?
N1 C10 . 1.383(4) ?
O3 N2 . 1.205(4) ?
O1 C7 . 1.218(4) ?
N3 N4 . 1.345(3) ?
N3 C15 . 1.382(3) ?
N3 C9 . 1.398(3) ?
C20 C21 . 1.379(4) ?
C20 C19 . 1.391(4) ?
C20 H20 . 0.93 ?
C17 C8 . 1.355(4) ?
C17 C16 . 1.414(4) ?
C17 H17 . 0.93 ?
C9 C8 . 1.425(4) ?
O2 N2 . 1.204(4) ?
N2 C13 . 1.469(4) ?
C13 C14 . 1.374(4) ?
C13 C12 . 1.395(4) ?
C14 C15 . 1.380(4) ?
C14 H14 . 0.93 ?
C15 C10 . 1.397(3) ?
N4 C16 . 1.309(3) ?
C16 C18 . 1.507(3) ?
C18 C19 . 1.465(3) ?
C19 C24 . 1.398(3) ?
C24 C23 . 1.373(4) ?
C24 H24 . 0.93 ?
C23 C22 . 1.395(4) ?
C23 H23 . 0.93 ?
C22 C21 . 1.379(4) ?
C25 H25A . 0.96 ?
C25 H25B . 0.96 ?
C25 H25C . 0.96 ?
C21 H21 . 0.93 ?
C8 C7 . 1.511(4) ?
C10 C11 . 1.393(4) ?
C12 C11 . 1.368(4) ?
C12 H12 . 0.93 ?
C11 H11 . 0.93 ?
C7 C4 . 1.475(4) ?
C4 C3 . 1.378(5) ?
C4 C5 . 1.392(4) ?
C5 C6 . 1.380(6) ?
C5 H5 . 0.93 ?
C6 C1 . 1.372(7) ?
C6 H6 . 0.93 ?
C1 C2 . 1.366(6) ?
C1 H1 . 0.93 ?
C2 C3 . 1.388(4) ?
C2 H2 . 0.93 ?
C3 H3 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C22 O5 C25 . . 117.2(2) ?
C9 N1 C10 . . 104.8(2) ?
N4 N3 C15 . . 125.8(2) ?
N4 N3 C9 . . 127.5(2) ?
C15 N3 C9 . . 106.76(19) ?
C21 C20 C19 . . 121.4(2) ?
C21 C20 H20 . . 119.3 ?
C19 C20 H20 . . 119.3 ?
C8 C17 C16 . . 121.3(3) ?
C8 C17 H17 . . 119.4 ?
C16 C17 H17 . . 119.4 ?
N1 C9 N3 . . 112.3(2) ?
N1 C9 C8 . . 131.9(2) ?
N3 C9 C8 . . 115.8(2) ?
O2 N2 O3 . . 123.0(3) ?
O2 N2 C13 . . 118.3(3) ?
O3 N2 C13 . . 118.7(3) ?
C14 C13 C12 . . 124.0(3) ?
C14 C13 N2 . . 117.7(3) ?
C12 C13 N2 . . 118.3(3) ?
C13 C14 C15 . . 114.3(2) ?
C13 C14 H14 . . 122.8 ?
C15 C14 H14 . . 122.8 ?
C14 C15 N3 . . 131.3(2) ?
C14 C15 C10 . . 124.1(2) ?
N3 C15 C10 . . 104.6(2) ?
C16 N4 N3 . . 114.6(2) ?
N4 C16 C17 . . 123.7(2) ?
N4 C16 C18 . . 116.7(2) ?
C17 C16 C18 . . 119.5(2) ?
O4 C18 C19 . . 122.6(2) ?
O4 C18 C16 . . 116.1(2) ?
C19 C18 C16 . . 121.3(2) ?
C20 C19 C24 . . 118.0(2) ?
C20 C19 C18 . . 123.3(2) ?
C24 C19 C18 . . 118.8(2) ?
C23 C24 C19 . . 121.0(2) ?
C23 C24 H24 . . 119.5 ?
C19 C24 H24 . . 119.5 ?
C24 C23 C22 . . 119.9(2) ?
C24 C23 H23 . . 120.0 ?
C22 C23 H23 . . 120.0 ?
O5 C22 C21 . . 124.5(3) ?
O5 C22 C23 . . 115.6(2) ?
C21 C22 C23 . . 119.9(2) ?
O5 C25 H25A . . 109.5 ?
O5 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
O5 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
C20 C21 C22 . . 119.8(3) ?
C20 C21 H21 . . 120.1 ?
C22 C21 H21 . . 120.1 ?
C17 C8 C9 . . 117.2(2) ?
C17 C8 C7 . . 119.9(3) ?
C9 C8 C7 . . 122.8(2) ?
N1 C10 C11 . . 129.3(2) ?
N1 C10 C15 . . 111.5(2) ?
C11 C10 C15 . . 119.2(3) ?
C11 C12 C13 . . 120.2(3) ?
C11 C12 H12 . . 119.9 ?
C13 C12 H12 . . 119.9 ?
C12 C11 C10 . . 118.3(3) ?
C12 C11 H11 . . 120.8 ?
C10 C11 H11 . . 120.8 ?
O1 C7 C4 . . 121.7(3) ?
O1 C7 C8 . . 116.9(3) ?
C4 C7 C8 . . 121.2(3) ?
C3 C4 C5 . . 119.4(3) ?
C3 C4 C7 . . 122.1(3) ?
C5 C4 C7 . . 118.4(3) ?
C6 C5 C4 . . 119.8(4) ?
C6 C5 H5 . . 120.1 ?
C4 C5 H5 . . 120.1 ?
C1 C6 C5 . . 120.2(4) ?
C1 C6 H6 . . 119.9 ?
C5 C6 H6 . . 119.9 ?
C2 C1 C6 . . 120.6(4) ?
C2 C1 H1 . . 119.7 ?
C6 C1 H1 . . 119.7 ?
C1 C2 C3 . . 119.8(4) ?
C1 C2 H2 . . 120.1 ?
C3 C2 H2 . . 120.1 ?
C4 C3 C2 . . 120.3(4) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 N1 C9 N3 . . . . 0.7(3) ?
C10 N1 C9 C8 . . . . 179.4(3) ?
N4 N3 C9 N1 . . . . 179.1(2) ?
C15 N3 C9 N1 . . . . -0.8(3) ?
N4 N3 C9 C8 . . . . 0.1(4) ?
C15 N3 C9 C8 . . . . -179.7(2) ?
O2 N2 C13 C14 . . . . -177.6(3) ?
O3 N2 C13 C14 . . . . 4.7(4) ?
O2 N2 C13 C12 . . . . 4.4(5) ?
O3 N2 C13 C12 . . . . -173.4(3) ?
C12 C13 C14 C15 . . . . 0.5(4) ?
N2 C13 C14 C15 . . . . -177.4(2) ?
C13 C14 C15 N3 . . . . 177.0(3) ?
C13 C14 C15 C10 . . . . 0.1(4) ?
N4 N3 C15 C14 . . . . 3.3(4) ?
C9 N3 C15 C14 . . . . -176.8(3) ?
N4 N3 C15 C10 . . . . -179.3(2) ?
C9 N3 C15 C10 . . . . 0.5(3) ?
C15 N3 N4 C16 . . . . 179.2(2) ?
C9 N3 N4 C16 . . . . -0.6(3) ?
N3 N4 C16 C17 . . . . 0.5(3) ?
N3 N4 C16 C18 . . . . 176.1(2) ?
C8 C17 C16 N4 . . . . 0.1(4) ?
C8 C17 C16 C18 . . . . -175.4(2) ?
N4 C16 C18 O4 . . . . -142.6(3) ?
C17 C16 C18 O4 . . . . 33.2(4) ?
N4 C16 C18 C19 . . . . 37.3(4) ?
C17 C16 C18 C19 . . . . -146.8(3) ?
C21 C20 C19 C24 . . . . 0.9(4) ?
C21 C20 C19 C18 . . . . 179.8(3) ?
O4 C18 C19 C20 . . . . -166.3(3) ?
C16 C18 C19 C20 . . . . 13.8(4) ?
O4 C18 C19 C24 . . . . 12.5(4) ?
C16 C18 C19 C24 . . . . -167.4(2) ?
C20 C19 C24 C23 . . . . -1.2(4) ?
C18 C19 C24 C23 . . . . 179.9(3) ?
C19 C24 C23 C22 . . . . 1.2(4) ?
C25 O5 C22 C21 . . . . -1.8(4) ?
C25 O5 C22 C23 . . . . 178.3(3) ?
C24 C23 C22 O5 . . . . 179.1(3) ?
C24 C23 C22 C21 . . . . -0.8(4) ?
C19 C20 C21 C22 . . . . -0.5(4) ?
O5 C22 C21 C20 . . . . -179.4(3) ?
C23 C22 C21 C20 . . . . 0.5(4) ?
C16 C17 C8 C9 . . . . -0.6(4) ?
C16 C17 C8 C7 . . . . -177.6(2) ?
N1 C9 C8 C17 . . . . -178.2(3) ?
N3 C9 C8 C17 . . . . 0.5(3) ?
N1 C9 C8 C7 . . . . -1.3(5) ?
N3 C9 C8 C7 . . . . 177.3(2) ?
C9 N1 C10 C11 . . . . 177.2(3) ?
C9 N1 C10 C15 . . . . -0.3(3) ?
C14 C15 C10 N1 . . . . 177.5(2) ?
N3 C15 C10 N1 . . . . -0.1(3) ?
C14 C15 C10 C11 . . . . -0.4(4) ?
N3 C15 C10 C11 . . . . -178.0(2) ?
C14 C13 C12 C11 . . . . -0.7(5) ?
N2 C13 C12 C11 . . . . 177.2(3) ?
C13 C12 C11 C10 . . . . 0.4(4) ?
N1 C10 C11 C12 . . . . -177.3(3) ?
C15 C10 C11 C12 . . . . 0.1(4) ?
C17 C8 C7 O1 . . . . 41.7(4) ?
C9 C8 C7 O1 . . . . -135.1(3) ?
C17 C8 C7 C4 . . . . -134.0(3) ?
C9 C8 C7 C4 . . . . 49.2(4) ?
O1 C7 C4 C3 . . . . -157.6(3) ?
C8 C7 C4 C3 . . . . 17.9(4) ?
O1 C7 C4 C5 . . . . 18.7(4) ?
C8 C7 C4 C5 . . . . -165.7(3) ?
C3 C4 C5 C6 . . . . -0.1(5) ?
C7 C4 C5 C6 . . . . -176.6(3) ?
C4 C5 C6 C1 . . . . 0.9(6) ?
C5 C6 C1 C2 . . . . -1.1(7) ?
C6 C1 C2 C3 . . . . 0.3(6) ?
C5 C4 C3 C2 . . . . -0.6(5) ?
C7 C4 C3 C2 . . . . 175.7(3) ?
C1 C2 C3 C4 . . . . 0.5(5) ?

