# 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_zccuno_0m
_database_code_depnum_ccdc_archive 'CCDC 1457400'
_audit_update_record             
;
2016-05-21 deposited with the CCDC.
2016-09-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H39 N24 O13'
_chemical_formula_weight         739.68

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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   11.1811(4)
_cell_length_b                   11.6175(5)
_cell_length_c                   14.5096(6)
_cell_angle_alpha                70.505(2)
_cell_angle_beta                 78.122(2)
_cell_angle_gamma                74.189(2)
_cell_volume                     1695.70(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          200
_exptl_crystal_size_mid          50
_exptl_crystal_size_min          50
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             778
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33721
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         27.55
_reflns_number_total             7780
_reflns_number_gt                5902
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1000P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7780
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1938
_refine_ls_wR_factor_gt          0.1766
_refine_ls_goodness_of_fit_ref   1.399
_refine_ls_restrained_S_all      1.399
_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
O1 O 0.99825(12) -0.19536(13) -0.02673(11) 0.0632(4) Uani 1 1 d . . .
C4 C 0.79849(15) 0.11487(17) -0.12396(13) 0.0440(4) Uani 1 1 d . . .
H4A H 0.8007 0.1896 -0.1740 0.053 Uiso 1 1 calc R . .
C15 C 0.1558(2) 0.5454(2) 0.15342(16) 0.0668(6) Uani 1 1 d . . .
H15A H 0.1008 0.5909 0.1929 0.080 Uiso 1 1 calc R . .
C14 C 0.10987(19) 0.4962(2) 0.09763(16) 0.0648(6) Uani 1 1 d . . .
H14A H 0.0238 0.5086 0.0995 0.078 Uiso 1 1 calc R . .
N1 N 0.51102(12) 0.25214(13) 0.00106(9) 0.0371(3) Uani 1 1 d . . .
H1A H 0.5328 0.2307 0.0590 0.045 Uiso 1 1 calc R . .
O2 O 0.48506(12) 0.27178(13) -0.31471(9) 0.0521(3) Uani 1 1 d . . .
O3 O 0.21435(15) 0.40001(15) -0.19661(14) 0.0815(5) Uani 1 1 d . . .
C37 C 0.65991(16) -0.03071(16) 0.67800(12) 0.0415(4) Uani 1 1 d . . .
H37A H 0.5740 -0.0005 0.6903 0.050 Uiso 1 1 calc R . .
N2 N 0.54823(11) 0.17768(12) 0.51447(9) 0.0348(3) Uani 1 1 d . . .
H2A H 0.5261 0.1986 0.5681 0.042 Uiso 1 1 calc R . .
O5 O 0.08426(14) 0.65020(15) 0.40716(14) 0.0793(5) Uani 1 1 d . . .
O6 O 0.58651(11) 0.17408(13) 0.19608(8) 0.0509(3) Uani 1 1 d . . .
O7 O 0.85215(11) -0.00401(14) 0.32937(11) 0.0619(4) Uani 1 1 d . . .
O8 O 0.69630(12) -0.09598(13) 0.34946(11) 0.0590(4) Uani 1 1 d . . .
C3 C 0.90487(15) 0.01817(17) -0.11519(14) 0.0463(4) Uani 1 1 d . . .
H3A H 0.9775 0.0282 -0.1589 0.056 Uiso 1 1 calc R . .
C5 C 0.68862(14) 0.10233(15) -0.05942(12) 0.0374(4) Uani 1 1 d . . .
C8 C 0.57521(14) 0.20264(15) -0.07227(12) 0.0361(4) Uani 1 1 d . . .
C9 C 0.50999(14) 0.26168(15) -0.15401(12) 0.0369(4) Uani 1 1 d . . .
C16 C 0.2829(2) 0.52753(19) 0.15081(15) 0.0581(5) Uani 1 1 d . . .
H16A H 0.3140 0.5603 0.1890 0.070 Uiso 1 1 calc R . .
C13 C 0.19090(16) 0.42812(19) 0.03856(14) 0.0520(5) Uani 1 1 d . . .
H13A H 0.1591 0.3939 0.0018 0.062 Uiso 1 1 calc R . .
C12 C 0.31975(15) 0.41100(15) 0.03428(11) 0.0382(4) Uani 1 1 d . . .
C17 C 0.36474(17) 0.46085(16) 0.09142(12) 0.0438(4) Uani 1 1 d . . .
H17A H 0.4507 0.4493 0.0898 0.053 Uiso 1 1 calc R . .
C11 C 0.40599(14) 0.34174(15) -0.03044(11) 0.0364(4) Uani 1 1 d . . .
C7 C 0.79326(17) -0.10683(18) 0.02434(14) 0.0494(4) Uani 1 1 d . . .
H7A H 0.7913 -0.1816 0.0744 0.059 Uiso 1 1 calc R . .
C6 C 0.68865(16) -0.01057(17) 0.01551(13) 0.0451(4) Uani 1 1 d . . .
H6A H 0.6168 -0.0208 0.0601 0.054 Uiso 1 1 calc R . .
C35 C 0.85329(19) -0.15329(19) 0.73792(15) 0.0569(5) Uani 1 1 d . . .
H35A H 0.8977 -0.2052 0.7898 0.068 Uiso 1 1 calc R . .
C36 C 0.72625(19) -0.10720(18) 0.75518(13) 0.0534(5) Uani 1 1 d . . .
H36A H 0.6849 -0.1276 0.8190 0.064 Uiso 1 1 calc R . .
C32 C 0.72072(14) 0.00163(14) 0.58167(11) 0.0338(3) Uani 1 1 d . . .
C31 C 0.64816(13) 0.08197(14) 0.50036(11) 0.0317(3) Uani 1 1 d . . .
C28 C 0.48981(14) 0.23426(15) 0.43270(11) 0.0344(3) Uani 1 1 d . . .
C25 C 0.38340(14) 0.34258(15) 0.42734(11) 0.0363(4) Uani 1 1 d . . .
C24 C 0.39922(17) 0.45253(19) 0.43592(17) 0.0578(5) Uani 1 1 d . . .
H24A H 0.4774 0.4566 0.4457 0.069 Uiso 1 1 calc R . .
C23 C 0.30129(18) 0.5567(2) 0.43031(18) 0.0607(5) Uani 1 1 d . . .
H23A H 0.3140 0.6298 0.4359 0.073 Uiso 1 1 calc R . .
C34 C 0.91447(17) -0.12201(19) 0.64311(15) 0.0537(5) Uani 1 1 d . . .
H34A H 1.0003 -0.1529 0.6312 0.064 Uiso 1 1 calc R . .
C33 C 0.84852(15) -0.04479(17) 0.56547(13) 0.0424(4) Uani 1 1 d . . .
H33A H 0.8906 -0.0240 0.5019 0.051 Uiso 1 1 calc R . .
C29 C 0.55315(14) 0.17428(15) 0.36215(11) 0.0346(3) Uani 1 1 d . . .
C40 C 0.52716(15) 0.21638(16) 0.26243(12) 0.0413(4) Uani 1 1 d . . .
H40A H 0.4584 0.2823 0.2467 0.050 Uiso 1 1 calc R . .
C26 C 0.26616(16) 0.33991(18) 0.41229(15) 0.0511(5) Uani 1 1 d . . .
H26A H 0.2532 0.2676 0.4055 0.061 Uiso 1 1 calc R . .
C1 C 1.11577(18) -0.1847(2) -0.08574(18) 0.0691(6) Uani 1 1 d . . .
H1B H 1.1751 -0.2631 -0.0676 0.104 Uiso 1 1 calc R . .
H1C H 1.1457 -0.1206 -0.0754 0.104 Uiso 1 1 calc R . .
H1D H 1.1057 -0.1633 -0.1540 0.104 Uiso 1 1 calc R . .
C2 C 0.90182(15) -0.09322(17) -0.04095(14) 0.0450(4) Uani 1 1 d . . .
C10 C 0.40300(14) 0.34926(15) -0.12628(11) 0.0360(4) Uani 1 1 d . . .
C19 C 0.30457(16) 0.43106(17) -0.18882(12) 0.0441(4) Uani 1 1 d . . .
O4 O 0.32486(17) 0.54070(16) -0.23506(16) 0.1048(8) Uani 1 1 d . . .
C20 C 0.2300(3) 0.6235(3) -0.2987(3) 0.1481(19) Uani 1 1 d . . .
H20A H 0.2522 0.7030 -0.3304 0.222 Uiso 1 1 calc R . .
H20B H 0.1498 0.6351 -0.2595 0.222 Uiso 1 1 calc R . .
H20C H 0.2261 0.5864 -0.3477 0.222 Uiso 1 1 calc R . .
C18 C 0.54262(16) 0.22723(17) -0.24297(13) 0.0439(4) Uani 1 1 d . . .
H18A H 0.6145 0.1649 -0.2469 0.053 Uiso 1 1 calc R . .
C22 C 0.18575(16) 0.55133(18) 0.41655(14) 0.0509(5) Uani 1 1 d . . .
C21 C 0.1001(3) 0.7635(2) 0.4170(2) 0.0900(9) Uani 1 1 d . . .
H21A H 0.0230 0.8254 0.4089 0.135 Uiso 1 1 calc R . .
H21B H 0.1651 0.7934 0.3675 0.135 Uiso 1 1 calc R . .
H21C H 0.1227 0.7476 0.4811 0.135 Uiso 1 1 calc R . .
C30 C 0.65346(13) 0.07819(14) 0.40598(11) 0.0328(3) Uani 1 1 d . . .
C38 C 0.74542(14) -0.00999(15) 0.35757(11) 0.0353(4) Uani 1 1 d . . .
C39 C 0.7789(2) -0.1863(3) 0.3036(2) 0.0815(8) Uani 1 1 d . . .
H39A H 0.7337 -0.2447 0.3017 0.122 Uiso 1 1 calc R . .
H39B H 0.8479 -0.2304 0.3408 0.122 Uiso 1 1 calc R . .
H39C H 0.8100 -0.1439 0.2376 0.122 Uiso 1 1 calc R . .
C27 C 0.16846(17) 0.4428(2) 0.40728(17) 0.0600(5) Uani 1 1 d . . .
H27A H 0.0901 0.4391 0.3976 0.072 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.358(2) . ?
O1 C1 1.425(2) . ?
C4 C3 1.390(2) . ?
C4 C5 1.393(2) . ?
C4 H4A 0.9300 . ?
C15 C14 1.373(3) . ?
C15 C16 1.374(3) . ?
C15 H15A 0.9300 . ?
C14 C13 1.387(3) . ?
C14 H14A 0.9300 . ?
N1 C8 1.3590(19) . ?
N1 C11 1.382(2) . ?
N1 H1A 0.8600 . ?
O2 C18 1.225(2) . ?
O3 C19 1.197(2) . ?
C37 C36 1.383(2) . ?
C37 C32 1.398(2) . ?
C37 H37A 0.9300 . ?
N2 C28 1.3531(19) . ?
N2 C31 1.3811(19) . ?
N2 H2A 0.8600 . ?
O5 C22 1.369(2) . ?
O5 C21 1.430(3) . ?
O6 C40 1.2180(19) . ?
O7 C38 1.1922(19) . ?
O8 C38 1.311(2) . ?
O8 C39 1.443(2) . ?
C3 C2 1.384(3) . ?
C3 H3A 0.9300 . ?
C5 C6 1.397(2) . ?
C5 C8 1.466(2) . ?
C8 C9 1.396(2) . ?
C9 C18 1.425(2) . ?
C9 C10 1.428(2) . ?
C16 C17 1.384(3) . ?
C16 H16A 0.9300 . ?
C13 C12 1.391(2) . ?
C13 H13A 0.9300 . ?
C12 C17 1.388(2) . ?
C12 C11 1.472(2) . ?
C17 H17A 0.9300 . ?
C11 C10 1.371(2) . ?
C7 C6 1.374(2) . ?
C7 C2 1.388(3) . ?
C7 H7A 0.9300 . ?
C6 H6A 0.9300 . ?
C35 C34 1.381(3) . ?
C35 C36 1.377(3) . ?
C35 H35A 0.9300 . ?
C36 H36A 0.9300 . ?
C32 C33 1.384(2) . ?
C32 C31 1.472(2) . ?
C31 C30 1.373(2) . ?
C28 C29 1.394(2) . ?
C28 C25 1.470(2) . ?
C25 C24 1.384(2) . ?
C25 C26 1.383(2) . ?
C24 C23 1.385(3) . ?
C24 H24A 0.9300 . ?
C23 C22 1.368(3) . ?
C23 H23A 0.9300 . ?
C34 C33 1.387(2) . ?
C34 H34A 0.9300 . ?
C33 H33A 0.9300 . ?
C29 C40 1.428(2) . ?
C29 C30 1.430(2) . ?
C40 H40A 0.9300 . ?
C26 C27 1.375(2) . ?
C26 H26A 0.9300 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?
C10 C19 1.484(2) . ?
C19 O4 1.284(2) . ?
O4 C20 1.468(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C18 H18A 0.9300 . ?
C22 C27 1.380(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C30 C38 1.486(2) . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C27 H27A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 118.34(16) . . ?
C3 C4 C5 121.44(16) . . ?
C3 C4 H4A 119.3 . . ?
C5 C4 H4A 119.3 . . ?
C14 C15 C16 119.94(17) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C15 C14 C13 120.53(19) . . ?
C15 C14 H14A 119.7 . . ?
C13 C14 H14A 119.7 . . ?
C8 N1 C11 110.58(13) . . ?
C8 N1 H1A 124.7 . . ?
C11 N1 H1A 124.7 . . ?
C36 C37 C32 120.63(16) . . ?
C36 C37 H37A 119.7 . . ?
C32 C37 H37A 119.7 . . ?
C28 N2 C31 111.00(12) . . ?
C28 N2 H2A 124.5 . . ?
C31 N2 H2A 124.5 . . ?
C22 O5 C21 117.25(17) . . ?
C38 O8 C39 116.43(14) . . ?
C2 C3 C4 119.44(16) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C4 C5 C6 117.89(15) . . ?
C4 C5 C8 120.95(15) . . ?
C6 C5 C8 121.12(14) . . ?
N1 C8 C9 107.20(13) . . ?
N1 C8 C5 122.94(14) . . ?
C9 C8 C5 129.81(14) . . ?
C8 C9 C18 123.76(15) . . ?
C8 C9 C10 107.15(13) . . ?
C18 C9 C10 128.81(15) . . ?
C15 C16 C17 120.10(19) . . ?
C15 C16 H16A 120.0 . . ?
C17 C16 H16A 120.0 . . ?
C12 C13 C14 119.98(18) . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C17 C12 C13 118.82(15) . . ?
C17 C12 C11 121.06(15) . . ?
C13 C12 C11 120.12(15) . . ?
C12 C17 C16 120.62(18) . . ?
C12 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?
C10 C11 N1 107.55(13) . . ?
C10 C11 C12 130.48(14) . . ?
N1 C11 C12 121.97(14) . . ?
C6 C7 C2 120.43(17) . . ?
C6 C7 H7A 119.8 . . ?
C2 C7 H7A 119.8 . . ?
C7 C6 C5 121.00(16) . . ?
C7 C6 H6A 119.5 . . ?
C5 C6 H6A 119.5 . . ?
C34 C35 C36 119.64(17) . . ?
C34 C35 H35A 120.2 . . ?
C36 C35 H35A 120.2 . . ?
C37 C36 C35 120.29(18) . . ?
C37 C36 H36A 119.9 . . ?
C35 C36 H36A 119.9 . . ?
C33 C32 C37 118.46(14) . . ?
C33 C32 C31 121.74(14) . . ?
C37 C32 C31 119.79(14) . . ?
C30 C31 N2 107.10(13) . . ?
C30 C31 C32 132.13(14) . . ?
N2 C31 C32 120.63(13) . . ?
N2 C28 C29 107.30(13) . . ?
N2 C28 C25 121.69(13) . . ?
C29 C28 C25 130.95(14) . . ?
C24 C25 C26 117.79(15) . . ?
C24 C25 C28 120.06(15) . . ?
C26 C25 C28 122.15(15) . . ?
C25 C24 C23 121.55(17) . . ?
C25 C24 H24A 119.2 . . ?
C23 C24 H24A 119.2 . . ?
C22 C23 C24 119.60(18) . . ?
C22 C23 H23A 120.2 . . ?
C24 C23 H23A 120.2 . . ?
C35 C34 C33 120.32(17) . . ?
C35 C34 H34A 119.8 . . ?
C33 C34 H34A 119.8 . . ?
C32 C33 C34 120.65(17) . . ?
C32 C33 H33A 119.7 . . ?
C34 C33 H33A 119.7 . . ?
C28 C29 C40 123.66(14) . . ?
C28 C29 C30 106.99(13) . . ?
C40 C29 C30 128.91(14) . . ?
O6 C40 C29 126.18(15) . . ?
O6 C40 H40A 116.9 . . ?
C29 C40 H40A 116.9 . . ?
C27 C26 C25 120.89(17) . . ?
C27 C26 H26A 119.6 . . ?
C25 C26 H26A 119.6 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C1 H1D 109.5 . . ?
H1B C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?
O1 C2 C3 124.85(16) . . ?
O1 C2 C7 115.35(17) . . ?
C3 C2 C7 119.79(15) . . ?
C11 C10 C9 107.52(14) . . ?
C11 C10 C19 126.17(14) . . ?
C9 C10 C19 126.30(14) . . ?
O3 C19 O4 122.16(17) . . ?
O3 C19 C10 124.43(17) . . ?
O4 C19 C10 113.42(16) . . ?
C19 O4 C20 114.79(18) . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C18 C9 126.25(16) . . ?
O2 C18 H18A 116.9 . . ?
C9 C18 H18A 116.9 . . ?
O5 C22 C23 123.95(19) . . ?
O5 C22 C27 116.37(17) . . ?
C23 C22 C27 119.63(17) . . ?
O5 C21 H21A 109.5 . . ?
O5 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O5 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C31 C30 C29 107.61(13) . . ?
C31 C30 C38 126.67(14) . . ?
C29 C30 C38 125.71(13) . . ?
O7 C38 O8 123.42(14) . . ?
O7 C38 C30 124.13(15) . . ?
O8 C38 C30 112.45(13) . . ?
O8 C39 H39A 109.5 . . ?
O8 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
O8 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C26 C27 C22 120.53(17) . . ?
C26 C27 H27A 119.7 . . ?
C22 C27 H27A 119.7 . . ?

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
C16 C15 C14 C13 0.1(3) . . . . ?
C5 C4 C3 C2 0.1(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C3 C4 C5 C8 -177.02(15) . . . . ?
C11 N1 C8 C9 -0.05(18) . . . . ?
C11 N1 C8 C5 -177.92(15) . . . . ?
C4 C5 C8 N1 -127.08(18) . . . . ?
C6 C5 C8 N1 55.4(2) . . . . ?
C4 C5 C8 C9 55.6(3) . . . . ?
C6 C5 C8 C9 -122.0(2) . . . . ?
N1 C8 C9 C18 -174.46(16) . . . . ?
C5 C8 C9 C18 3.2(3) . . . . ?
N1 C8 C9 C10 -0.08(18) . . . . ?
C5 C8 C9 C10 177.59(17) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C15 C14 C13 C12 -1.0(3) . . . . ?
C14 C13 C12 C17 1.3(3) . . . . ?
C14 C13 C12 C11 -178.32(18) . . . . ?
C13 C12 C17 C16 -0.7(3) . . . . ?
C11 C12 C17 C16 178.95(17) . . . . ?
C15 C16 C17 C12 -0.3(3) . . . . ?
C8 N1 C11 C10 0.17(18) . . . . ?
C8 N1 C11 C12 -179.64(15) . . . . ?
C17 C12 C11 C10 -134.53(19) . . . . ?
C13 C12 C11 C10 45.1(3) . . . . ?
C17 C12 C11 N1 45.2(2) . . . . ?
C13 C12 C11 N1 -135.14(17) . . . . ?
C2 C7 C6 C5 0.5(3) . . . . ?
C4 C5 C6 C7 -0.9(3) . . . . ?
C8 C5 C6 C7 176.68(16) . . . . ?
C32 C37 C36 C35 -0.4(3) . . . . ?
C34 C35 C36 C37 0.5(3) . . . . ?
C36 C37 C32 C33 0.1(2) . . . . ?
C36 C37 C32 C31 179.27(16) . . . . ?
C28 N2 C31 C30 0.26(18) . . . . ?
C28 N2 C31 C32 -175.97(13) . . . . ?
C33 C32 C31 C30 39.9(3) . . . . ?
C37 C32 C31 C30 -139.23(18) . . . . ?
C33 C32 C31 N2 -144.96(16) . . . . ?
C37 C32 C31 N2 35.9(2) . . . . ?
C31 N2 C28 C29 -0.10(18) . . . . ?
C31 N2 C28 C25 -177.50(14) . . . . ?
N2 C28 C25 C24 61.9(2) . . . . ?
C29 C28 C25 C24 -114.8(2) . . . . ?
N2 C28 C25 C26 -119.16(18) . . . . ?
C29 C28 C25 C26 64.1(3) . . . . ?
C26 C25 C24 C23 0.4(3) . . . . ?
C28 C25 C24 C23 179.40(19) . . . . ?
C25 C24 C23 C22 0.4(3) . . . . ?
C36 C35 C34 C33 -0.1(3) . . . . ?
C37 C32 C33 C34 0.2(3) . . . . ?
C31 C32 C33 C34 -178.92(16) . . . . ?
C35 C34 C33 C32 -0.2(3) . . . . ?
N2 C28 C29 C40 -173.06(15) . . . . ?
C25 C28 C29 C40 4.0(3) . . . . ?
N2 C28 C29 C30 -0.09(18) . . . . ?
C25 C28 C29 C30 176.98(16) . . . . ?
C28 C29 C40 O6 173.24(17) . . . . ?
C30 C29 C40 O6 1.9(3) . . . . ?
C24 C25 C26 C27 -0.8(3) . . . . ?
C28 C25 C26 C27 -179.78(17) . . . . ?
C1 O1 C2 C3 6.5(3) . . . . ?
C1 O1 C2 C7 -174.87(18) . . . . ?
C4 C3 C2 O1 177.99(17) . . . . ?
C4 C3 C2 C7 -0.6(3) . . . . ?
C6 C7 C2 O1 -178.45(17) . . . . ?
C6 C7 C2 C3 0.2(3) . . . . ?
N1 C11 C10 C9 -0.22(18) . . . . ?
C12 C11 C10 C9 179.57(17) . . . . ?
N1 C11 C10 C19 178.25(16) . . . . ?
C12 C11 C10 C19 -2.0(3) . . . . ?
C8 C9 C10 C11 0.19(19) . . . . ?
C18 C9 C10 C11 174.19(17) . . . . ?
C8 C9 C10 C19 -178.28(16) . . . . ?
C18 C9 C10 C19 -4.3(3) . . . . ?
C11 C10 C19 O3 -92.4(2) . . . . ?
C9 C10 C19 O3 85.8(2) . . . . ?
C11 C10 C19 O4 87.7(2) . . . . ?
C9 C10 C19 O4 -94.2(2) . . . . ?
O3 C19 O4 C20 -0.8(4) . . . . ?
C10 C19 O4 C20 179.2(3) . . . . ?
C8 C9 C18 O2 176.18(17) . . . . ?
C10 C9 C18 O2 3.1(3) . . . . ?
C21 O5 C22 C23 -2.9(3) . . . . ?
C21 O5 C22 C27 179.7(2) . . . . ?
C24 C23 C22 O5 -178.0(2) . . . . ?
C24 C23 C22 C27 -0.8(3) . . . . ?
N2 C31 C30 C29 -0.30(17) . . . . ?
C32 C31 C30 C29 175.31(15) . . . . ?
N2 C31 C30 C38 -179.75(14) . . . . ?
C32 C31 C30 C38 -4.1(3) . . . . ?
C28 C29 C30 C31 0.25(18) . . . . ?
C40 C29 C30 C31 172.73(16) . . . . ?
C28 C29 C30 C38 179.70(15) . . . . ?
C40 C29 C30 C38 -7.8(3) . . . . ?
C39 O8 C38 O7 0.0(3) . . . . ?
C39 O8 C38 C30 -179.80(19) . . . . ?
C31 C30 C38 O7 -73.9(2) . . . . ?
C29 C30 C38 O7 106.7(2) . . . . ?
C31 C30 C38 O8 105.83(18) . . . . ?
C29 C30 C38 O8 -73.5(2) . . . . ?
C25 C26 C27 C22 0.4(3) . . . . ?
O5 C22 C27 C26 177.80(19) . . . . ?
C23 C22 C27 C26 0.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.107
####################################################################### 
# 
# 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_b151009a_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1457401'
_audit_update_record             
;
2016-03-03 deposited with the CCDC.
2016-09-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H13 N O4'
_chemical_formula_sum            'C19 H13 N O4'
_chemical_formula_weight         319.30

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   10.7549(6)
_cell_length_b                   7.0492(4)
_cell_length_c                   19.1664(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.500(2)
_cell_angle_gamma                90.00
_cell_volume                     1418.63(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9993
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      27.51

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9199
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27173
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         27.54
_reflns_number_total             3257
_reflns_number_gt                2574
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.0630P)²+0.5362P] 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         3257
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1298
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
O1 O -0.01112(11) 0.24652(18) 0.50341(6) 0.0311(3) Uani 1 1 d . . .
O2 O 0.11373(12) 0.2858(2) 0.42486(6) 0.0370(3) Uani 1 1 d . . .
O3 O 0.42422(10) 0.41787(16) 0.56207(5) 0.0236(3) Uani 1 1 d . . .
O4 O 0.07881(11) 0.42802(18) 0.94084(6) 0.0285(3) Uani 1 1 d . . .
N1 N 0.32988(11) 0.38169(17) 0.65535(6) 0.0169(3) Uani 1 1 d . . .
C1 C 0.10412(16) 0.2862(2) 0.48640(9) 0.0265(4) Uani 1 1 d . . .
C2 C 0.19304(14) 0.3237(2) 0.55280(8) 0.0209(3) Uani 1 1 d . . .
C3 C 0.13070(14) 0.3084(2) 0.61044(8) 0.0199(3) Uani 1 1 d . . .
C4 C -0.00377(15) 0.2514(3) 0.58020(8) 0.0273(4) Uani 1 1 d . . .
H4A H -0.0220 0.1277 0.5978 0.033 Uiso 1 1 calc R . .
H4B H -0.0630 0.3433 0.5921 0.033 Uiso 1 1 calc R . .
C5 C 0.31584(14) 0.3706(2) 0.58326(8) 0.0195(3) Uani 1 1 d . . .
C6 C 0.51020(14) 0.4652(2) 0.62512(8) 0.0207(3) Uani 1 1 d . . .
C7 C 0.63246(15) 0.5300(2) 0.62990(9) 0.0254(4) Uani 1 1 d . . .
H7 H 0.6666 0.5461 0.5897 0.030 Uiso 1 1 calc R . .
C8 C 0.70174(15) 0.5697(2) 0.69793(9) 0.0272(4) Uani 1 1 d . . .
H8 H 0.7847 0.6145 0.7039 0.033 Uiso 1 1 calc R . .
C9 C 0.64953(15) 0.5439(2) 0.75760(9) 0.0262(4) Uani 1 1 d . . .
H9 H 0.6992 0.5695 0.8027 0.031 Uiso 1 1 calc R . .
C10 C 0.52511(15) 0.4808(2) 0.75178(9) 0.0220(3) Uani 1 1 d . . .
H10 H 0.4907 0.4644 0.7919 0.026 Uiso 1 1 calc R . .
C11 C 0.45516(14) 0.4436(2) 0.68405(8) 0.0183(3) Uani 1 1 d . . .
C12 C 0.21150(14) 0.3461(2) 0.67443(8) 0.0175(3) Uani 1 1 d . . .
C13 C 0.18555(14) 0.3644(2) 0.74583(8) 0.0174(3) Uani 1 1 d . . .
C14 C 0.26961(14) 0.3131(2) 0.80863(8) 0.0177(3) Uani 1 1 d . . .
H14 H 0.3487 0.2635 0.8062 0.021 Uiso 1 1 calc R . .
C15 C 0.23892(14) 0.3336(2) 0.87503(8) 0.0189(3) Uani 1 1 d . . .
H15 H 0.2975 0.3010 0.9165 0.023 Uiso 1 1 calc R . .
C16 C 0.11975(14) 0.4035(2) 0.87882(8) 0.0191(3) Uani 1 1 d . . .
C17 C 0.03356(14) 0.4541(2) 0.81658(8) 0.0207(3) Uani 1 1 d . . .
H17 H -0.0464 0.5000 0.8190 0.025 Uiso 1 1 calc R . .
C18 C 0.06617(14) 0.4364(2) 0.75148(8) 0.0194(3) Uani 1 1 d . . .
H18 H 0.0081 0.4727 0.7103 0.023 Uiso 1 1 calc R . .
C19 C 0.16410(17) 0.3790(3) 1.00596(9) 0.0310(4) Uani 1 1 d . . .
H19A H 0.1871 0.2476 1.0047 0.046 Uiso 1 1 calc R . .
H19B H 0.1235 0.4002 1.0452 0.046 Uiso 1 1 calc R . .
H19C H 0.2393 0.4560 1.0119 0.046 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.377(2) . ?
O1 C4 1.4572(19) . ?
O2 C1 1.206(2) . ?
O3 C5 1.3562(18) . ?
O3 C6 1.3940(18) . ?
O4 C16 1.3651(18) . ?
O4 C19 1.422(2) . ?
N1 C5 1.3593(19) . ?
N1 C11 1.4098(19) . ?
N1 C12 1.4211(18) . ?
C1 C2 1.441(2) . ?
C2 C5 1.364(2) . ?
C2 C3 1.415(2) . ?
C3 C12 1.367(2) . ?
C3 C4 1.492(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 C7 1.376(2) . ?
C6 C11 1.392(2) . ?
C7 C8 1.383(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.391(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.391(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(2) . ?
C10 H10 0.9300 . ?
C12 C13 1.460(2) . ?
C13 C14 1.388(2) . ?
C13 C18 1.406(2) . ?
C14 C15 1.390(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.389(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.390(2) . ?
C17 C18 1.373(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C4 112.30(12) . . ?
C5 O3 C6 104.55(11) . . ?
C16 O4 C19 117.70(12) . . ?
C5 N1 C11 107.52(12) . . ?
C5 N1 C12 110.05(12) . . ?
C11 N1 C12 142.00(12) . . ?
O2 C1 O1 120.21(15) . . ?
O2 C1 C2 133.08(16) . . ?
O1 C1 C2 106.71(13) . . ?
C5 C2 C3 105.23(13) . . ?
C5 C2 C1 144.92(15) . . ?
C3 C2 C1 109.84(14) . . ?
C12 C3 C2 111.67(14) . . ?
C12 C3 C4 140.84(15) . . ?
C2 C3 C4 107.48(13) . . ?
O1 C4 C3 103.59(13) . . ?
O1 C4 H4A 111.0 . . ?
C3 C4 H4A 111.0 . . ?
O1 C4 H4B 111.0 . . ?
C3 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
O3 C5 N1 112.12(13) . . ?
O3 C5 C2 138.30(14) . . ?
N1 C5 C2 109.47(13) . . ?
C7 C6 C11 123.38(15) . . ?
C7 C6 O3 125.61(14) . . ?
C11 C6 O3 110.99(13) . . ?
C6 C7 C8 116.23(15) . . ?
C6 C7 H7 121.9 . . ?
C8 C7 H7 121.9 . . ?
C7 C8 C9 121.17(15) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C10 121.89(15) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C11 C10 C9 117.14(15) . . ?
C11 C10 H10 121.4 . . ?
C9 C10 H10 121.4 . . ?
C10 C11 C6 120.15(14) . . ?
C10 C11 N1 135.05(14) . . ?
C6 C11 N1 104.81(13) . . ?
C3 C12 N1 103.55(12) . . ?
C3 C12 C13 130.14(14) . . ?
N1 C12 C13 126.10(13) . . ?
C14 C13 C18 117.48(13) . . ?
C14 C13 C12 124.67(13) . . ?
C18 C13 C12 117.84(13) . . ?
C13 C14 C15 121.85(13) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C16 C15 C14 119.31(14) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
O4 C16 C15 124.44(14) . . ?
O4 C16 C17 115.73(13) . . ?
C15 C16 C17 119.83(14) . . ?
C18 C17 C16 120.18(14) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C13 121.32(14) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.059
####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 1483111'
_audit_update_record             
;
2016-06-02 deposited with the CCDC.
2016-09-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 N O3'
_chemical_formula_sum            'C23 H21 N O3'
_chemical_formula_weight         359.41

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           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                   8.6755(7)
_cell_length_b                   10.6916(10)
_cell_length_c                   11.4390(9)
_cell_angle_alpha                69.968(8)
_cell_angle_beta                 73.363(7)
_cell_angle_gamma                72.428(7)
_cell_volume                     930.30(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    3662
_cell_measurement_theta_min      3.6130
_cell_measurement_theta_max      29.9250

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9750
_exptl_absorpt_correction_T_max  0.9832
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(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  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7518
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         25.49
_reflns_number_total             3444
_reflns_number_gt                2740
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0668P)²+0.1289P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    contr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3444
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1281
_refine_ls_wR_factor_gt          0.1181
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.72889(19) 0.43028(15) 0.24574(15) 0.0319(4) Uani 1 1 d . . .
C2 C 0.7874(2) 0.46074(17) 0.11603(17) 0.0431(4) Uani 1 1 d . . .
H2 H 0.8376 0.3895 0.0775 0.052 Uiso 1 1 calc R . .
C3 C 0.7728(2) 0.59536(19) 0.04205(18) 0.0497(5) Uani 1 1 d . . .
H3 H 0.8140 0.6151 -0.0462 0.060 Uiso 1 1 calc R . .
C4 C 0.6977(2) 0.70037(17) 0.09790(19) 0.0464(4) Uani 1 1 d . . .
H4 H 0.6868 0.7918 0.0479 0.056 Uiso 1 1 calc R . .
C5 C 0.6393(2) 0.67054(17) 0.22614(19) 0.0492(5) Uani 1 1 d . . .
H5 H 0.5880 0.7420 0.2643 0.059 Uiso 1 1 calc R . .
C6 C 0.6548(2) 0.53646(17) 0.30058(17) 0.0423(4) Uani 1 1 d . . .
H6 H 0.6148 0.5174 0.3889 0.051 Uiso 1 1 calc R . .
C7 C 0.73700(19) 0.28270(15) 0.32749(15) 0.0340(4) Uani 1 1 d . . .
C8 C 0.60054(19) 0.23019(15) 0.31262(15) 0.0323(4) Uani 1 1 d . . .
C9 C 0.67037(19) 0.12995(14) 0.25774(15) 0.0318(4) Uani 1 1 d . . .
C10 C 0.85266(19) 0.10650(14) 0.24024(15) 0.0321(4) Uani 1 1 d . . .
C11 C 0.97882(19) 0.00050(14) 0.18860(15) 0.0323(4) Uani 1 1 d . . .
C12 C 1.1450(2) 0.00400(16) 0.16046(15) 0.0362(4) Uani 1 1 d . . .
H12 H 1.1759 0.0749 0.1729 0.043 Uiso 1 1 calc R . .
C13 C 1.2647(2) -0.09643(17) 0.11431(16) 0.0409(4) Uani 1 1 d . . .
H13 H 1.3765 -0.0927 0.0941 0.049 Uiso 1 1 calc R . .
C14 C 1.2208(2) -0.20209(17) 0.09787(17) 0.0449(4) Uani 1 1 d . . .
H14 H 1.3028 -0.2709 0.0677 0.054 Uiso 1 1 calc R . .
C15 C 1.0568(2) -0.20693(17) 0.12557(18) 0.0454(4) Uani 1 1 d . . .
H15 H 1.0272 -0.2792 0.1146 0.054 Uiso 1 1 calc R . .
C16 C 0.9352(2) -0.10494(16) 0.16976(17) 0.0398(4) Uani 1 1 d . . .
H16 H 0.8233 -0.1073 0.1869 0.048 Uiso 1 1 calc R . .
C17 C 0.53780(19) 0.08599(15) 0.23550(16) 0.0357(4) Uani 1 1 d . . .
C18 C 0.41746(19) 0.26200(15) 0.33458(16) 0.0355(4) Uani 1 1 d . . .
C19 C 0.3280(2) 0.40447(17) 0.26907(19) 0.0458(4) Uani 1 1 d . . .
H19A H 0.3442 0.4172 0.1777 0.055 Uiso 1 1 calc R . .
H19B H 0.3669 0.4751 0.2816 0.055 Uiso 1 1 calc R . .
C20 C 0.1465(3) 0.4093(2) 0.3341(3) 0.0714(6) Uani 1 1 d . . .
H20A H 0.0894 0.5018 0.3404 0.086 Uiso 1 1 calc R . .
H20B H 0.0910 0.3832 0.2854 0.086 Uiso 1 1 calc R . .
C21 C 0.1448(3) 0.3105(3) 0.4636(3) 0.0920(9) Uani 1 1 d . . .
H21A H 0.0792 0.2447 0.4768 0.110 Uiso 1 1 calc R . .
H21B H 0.0958 0.3592 0.5289 0.110 Uiso 1 1 calc R . .
C22 C 0.3230(2) 0.2365(2) 0.47232(18) 0.0508(5) Uani 1 1 d . . .
H22A H 0.3316 0.1385 0.5134 0.061 Uiso 1 1 calc R . .
H22B H 0.3658 0.2737 0.5207 0.061 Uiso 1 1 calc R . .
C23 C 0.7480(3) 0.14688(19) 0.54077(19) 0.0596(5) Uani 1 1 d . . .
H23A H 0.6640 0.1040 0.5410 0.089 Uiso 1 1 calc R . .
H23B H 0.7360 0.1543 0.6253 0.089 Uiso 1 1 calc R . .
H23C H 0.8566 0.0919 0.5158 0.089 Uiso 1 1 calc R . .
N1 N 0.88993(16) 0.19089(13) 0.27985(14) 0.0369(3) Uani 1 1 d . . .
O1 O 0.39159(13) 0.16413(11) 0.28107(12) 0.0413(3) Uani 1 1 d . . .
O2 O 0.54207(14) -0.00038(12) 0.18888(13) 0.0480(3) Uani 1 1 d . . .
O3 O 0.72969(15) 0.28019(11) 0.45274(11) 0.0448(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 1.379(2) . ?
C1 C6 1.383(2) . ?
C1 C7 1.526(2) . ?
C2 C3 1.386(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.365(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.382(2) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 O3 1.4071(19) . ?
C7 N1 1.4788(19) . ?
C7 C8 1.526(2) . ?
C8 C9 1.327(2) . ?
C8 C18 1.485(2) . ?
C9 C17 1.478(2) . ?
C9 C10 1.489(2) . ?
C10 N1 1.2900(19) . ?
C10 C11 1.473(2) . ?
C11 C16 1.390(2) . ?
C11 C12 1.394(2) . ?
C12 C13 1.382(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.380(2) . ?
C13 H13 0.9400 . ?
C14 C15 1.379(2) . ?
C14 H14 0.9400 . ?
C15 C16 1.391(2) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
C17 O2 1.2015(18) . ?
C17 O1 1.3633(18) . ?
C18 O1 1.4762(17) . ?
C18 C19 1.524(2) . ?
C18 C22 1.526(2) . ?
C19 C20 1.530(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C20 C21 1.496(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C21 C22 1.524(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C23 O3 1.429(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.82(15) . . ?
C2 C1 C7 121.13(13) . . ?
C6 C1 C7 119.98(14) . . ?
C1 C2 C3 120.60(15) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 119.99(17) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 119.54(16) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.74(16) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 120.32(17) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O3 C7 N1 111.22(13) . . ?
O3 C7 C8 114.48(13) . . ?
N1 C7 C8 103.29(11) . . ?
O3 C7 C1 107.24(11) . . ?
N1 C7 C1 110.87(13) . . ?
C8 C7 C1 109.76(13) . . ?
C9 C8 C18 112.19(14) . . ?
C9 C8 C7 108.37(14) . . ?
C18 C8 C7 139.33(13) . . ?
C8 C9 C17 108.12(14) . . ?
C8 C9 C10 107.78(13) . . ?
C17 C9 C10 144.09(13) . . ?
N1 C10 C11 122.45(14) . . ?
N1 C10 C9 110.94(13) . . ?
C11 C10 C9 126.59(13) . . ?
C16 C11 C12 119.25(14) . . ?
C16 C11 C10 121.04(14) . . ?
C12 C11 C10 119.70(13) . . ?
C13 C12 C11 120.19(15) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 120.27(16) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 120.12(15) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.04(15) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 120.10(16) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
O2 C17 O1 121.33(14) . . ?
O2 C17 C9 131.72(15) . . ?
O1 C17 C9 106.95(12) . . ?
O1 C18 C8 101.22(11) . . ?
O1 C18 C19 107.74(13) . . ?
C8 C18 C19 118.56(13) . . ?
O1 C18 C22 107.65(12) . . ?
C8 C18 C22 117.19(15) . . ?
C19 C18 C22 103.80(13) . . ?
C18 C19 C20 103.78(15) . . ?
C18 C19 H19A 111.0 . . ?
C20 C19 H19A 111.0 . . ?
C18 C19 H19B 111.0 . . ?
C20 C19 H19B 111.0 . . ?
H19A C19 H19B 109.0 . . ?
C21 C20 C19 106.73(19) . . ?
C21 C20 H20A 110.4 . . ?
C19 C20 H20A 110.4 . . ?
C21 C20 H20B 110.4 . . ?
C19 C20 H20B 110.4 . . ?
H20A C20 H20B 108.6 . . ?
C20 C21 C22 107.58(18) . . ?
C20 C21 H21A 110.2 . . ?
C22 C21 H21A 110.2 . . ?
C20 C21 H21B 110.2 . . ?
C22 C21 H21B 110.2 . . ?
H21A C21 H21B 108.5 . . ?
C21 C22 C18 104.65(17) . . ?
C21 C22 H22A 110.8 . . ?
C18 C22 H22A 110.8 . . ?
C21 C22 H22B 110.8 . . ?
C18 C22 H22B 110.8 . . ?
H22A C22 H22B 108.9 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C10 N1 C7 109.51(12) . . ?
C17 O1 C18 111.50(11) . . ?
C7 O3 C23 114.54(13) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_g160613c
_database_code_depnum_ccdc_archive 'CCDC 1485648'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2016-09-27 downloaded from the CCDC.
;
_audit_creation_date             2016-06-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H16 Br N O3'
_chemical_formula_sum            'C20 H16 Br N O3'
_chemical_formula_weight         398.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Br'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   4.2880(5)
_cell_length_b                   27.2739(16)
_cell_length_c                   14.6976(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.213(8)
_cell_angle_gamma                90.00
_cell_volume                     1718.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1629
_cell_measurement_temperature    223.00(10)
_cell_measurement_theta_max      28.5230
_cell_measurement_theta_min      3.2880
_exptl_absorpt_coefficient_mu    2.410
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0682
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6334
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.77
_diffrn_ambient_temperature      223.00(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.879
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   39.00   74.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514   37.0000  -90.0000 35

#__ type_ start__ end____ width___ exp.time_
  2 omega    4.00   30.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514   37.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -86.00  -61.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.4327 -178.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega  -59.00   14.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.4327  -57.0000  120.0000 73
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1285201000
_diffrn_orient_matrix_UB_12      -0.0017823000
_diffrn_orient_matrix_UB_13      -0.0300404000
_diffrn_orient_matrix_UB_21      -0.1002098000
_diffrn_orient_matrix_UB_22      -0.0093577000
_diffrn_orient_matrix_UB_23      -0.0343916000
_diffrn_orient_matrix_UB_31      -0.0292885000
_diffrn_orient_matrix_UB_32      0.0241861000
_diffrn_orient_matrix_UB_33      -0.0155342000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2200
_reflns_number_total             3104
_reflns_odcompleteness_completeness 86.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0311P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0883
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9), C10(H10), C12(H12), C13(H13), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 0.12592(10) 0.514860(12) 0.31973(2) 0.04531(16) Uani 1 d . . .
O1 O -0.3002(6) 0.71303(8) -0.20062(13) 0.0350(6) Uani 1 d . . .
O2 O -0.5331(7) 0.78277(9) -0.17232(15) 0.0456(7) Uani 1 d . . .
O3 O -0.4777(6) 0.61937(7) -0.10093(14) 0.0318(6) Uani 1 d . . .
N1 N -0.3333(7) 0.73394(9) 0.10437(16) 0.0283(7) Uani 1 d . . .
H1 H -0.3411 0.7428 0.1605 0.034 Uiso 1 calc . . R
C1 C -0.3986(9) 0.74776(12) -0.1400(2) 0.0314(9) Uani 1 d . . .
C2 C -0.3463(8) 0.73601(11) -0.04502(19) 0.0242(8) Uani 1 d . . .
C3 C -0.2750(8) 0.68750(10) -0.01695(19) 0.0224(8) Uani 1 d . . .
C4 C -0.2045(8) 0.64859(11) -0.0846(2) 0.0282(8) Uani 1 d . . .
H4 H -0.0368 0.6276 -0.0611 0.034 Uiso 1 calc . . R
C5 C -0.0960(9) 0.67396(12) -0.1704(2) 0.0361(9) Uani 1 d . . .
H5A H 0.1105 0.6874 -0.1598 0.043 Uiso 1 calc . . R
H5B H -0.0792 0.6498 -0.2186 0.043 Uiso 1 calc . . R
C6 C -0.4095(11) 0.57374(13) -0.1426(3) 0.0554(12) Uani 1 d . . .
H6A H -0.3150 0.5793 -0.2008 0.083 Uiso 1 calc . . GR
H6B H -0.5989 0.5554 -0.1506 0.083 Uiso 1 calc . . GR
H6C H -0.2684 0.5555 -0.1046 0.083 Uiso 1 calc . . GR
C7 C -0.2697(8) 0.68690(11) 0.0754(2) 0.0258(8) Uani 1 d . . .
C8 C -0.1869(8) 0.64662(11) 0.1376(2) 0.0256(8) Uani 1 d . . .
C9 C -0.2791(9) 0.59893(11) 0.1175(2) 0.0332(9) Uani 1 d . . .
H9 H -0.4042 0.5931 0.0668 0.040 Uiso 1 calc . . R
C10 C -0.1880(9) 0.56026(12) 0.1714(2) 0.0384(10) Uani 1 d . . .
H10 H -0.2490 0.5285 0.1569 0.046 Uiso 1 calc . . R
C11 C -0.0064(9) 0.56900(11) 0.2467(2) 0.0332(9) Uani 1 d . . .
C12 C 0.0887(9) 0.61574(11) 0.2698(2) 0.0333(9) Uani 1 d . . .
H12 H 0.2117 0.6212 0.3210 0.040 Uiso 1 calc . . R
C13 C -0.0036(9) 0.65433(11) 0.2146(2) 0.0308(9) Uani 1 d . . .
H13 H 0.0581 0.6860 0.2293 0.037 Uiso 1 calc . . R
C14 C -0.3823(8) 0.76459(11) 0.0320(2) 0.0266(8) Uani 1 d . . .
C15 C -0.4481(8) 0.81726(11) 0.04337(19) 0.0264(8) Uani 1 d . . .
C16 C -0.6260(9) 0.83432(11) 0.1152(2) 0.0325(9) Uani 1 d . . .
H16 H -0.7080 0.8124 0.1573 0.039 Uiso 1 calc . . R
C17 C -0.6812(10) 0.88424(12) 0.1242(2) 0.0420(10) Uani 1 d . . .
H17 H -0.7990 0.8957 0.1728 0.050 Uiso 1 calc . . R
C18 C -0.5638(9) 0.91691(12) 0.0620(2) 0.0396(10) Uani 1 d . . .
H18 H -0.6051 0.9502 0.0679 0.047 Uiso 1 calc . . R
C19 C -0.3856(10) 0.90033(12) -0.0088(2) 0.0409(10) Uani 1 d . . .
H19 H -0.3060 0.9224 -0.0510 0.049 Uiso 1 calc . . R
C20 C -0.3239(9) 0.85071(11) -0.0176(2) 0.0368(10) Uani 1 d . . .
H20 H -0.1981 0.8397 -0.0647 0.044 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C11 1.911(3) . ?
O1 C1 1.368(4) . ?
O1 C5 1.448(4) . ?
O2 C1 1.212(4) . ?
O3 C4 1.437(4) . ?
O3 C6 1.418(4) . ?
N1 C7 1.380(4) . ?
N1 C14 1.368(4) . ?
C1 C2 1.449(4) . ?
C2 C3 1.419(4) . ?
C2 C14 1.384(4) . ?
C3 C4 1.486(4) . ?
C3 C7 1.357(4) . ?
C4 C5 1.514(4) . ?
C7 C8 1.472(4) . ?
C8 C9 1.391(4) . ?
C8 C13 1.392(5) . ?
C9 C10 1.375(4) . ?
C10 C11 1.372(5) . ?
C11 C12 1.381(4) . ?
C12 C13 1.385(4) . ?
C14 C15 1.474(4) . ?
C15 C16 1.386(4) . ?
C15 C20 1.386(4) . ?
C16 C17 1.388(4) . ?
C17 C18 1.374(5) . ?
C18 C19 1.370(5) . ?
C19 C20 1.385(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
C1 O1 C5 119.8(2) . . ?
C6 O3 C4 112.9(3) . . ?
C14 N1 C7 111.0(2) . . ?
O1 C1 C2 115.3(3) . . ?
O2 C1 O1 115.9(3) . . ?
O2 C1 C2 128.6(3) . . ?
C3 C2 C1 121.3(3) . . ?
C14 C2 C1 130.3(3) . . ?
C14 C2 C3 108.2(3) . . ?
C2 C3 C4 121.0(3) . . ?
C7 C3 C2 107.7(3) . . ?
C7 C3 C4 131.1(3) . . ?
O3 C4 C3 109.9(3) . . ?
O3 C4 C5 111.5(3) . . ?
C3 C4 C5 107.2(3) . . ?
O1 C5 C4 113.9(3) . . ?
N1 C7 C8 123.3(3) . . ?
C3 C7 N1 107.2(3) . . ?
C3 C7 C8 129.3(3) . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 C13 118.3(3) . . ?
C13 C8 C7 121.8(3) . . ?
C10 C9 C8 121.0(3) . . ?
C11 C10 C9 119.4(3) . . ?
C10 C11 Br1 119.1(2) . . ?
C10 C11 C12 121.7(3) . . ?
C12 C11 Br1 119.2(3) . . ?
C11 C12 C13 118.3(3) . . ?
C12 C13 C8 121.4(3) . . ?
N1 C14 C2 105.9(3) . . ?
N1 C14 C15 122.4(3) . . ?
C2 C14 C15 131.6(3) . . ?
C16 C15 C14 121.3(3) . . ?
C16 C15 C20 119.0(3) . . ?
C20 C15 C14 119.6(3) . . ?
C15 C16 C17 119.7(3) . . ?
C18 C17 C16 120.7(3) . . ?
C19 C18 C17 119.9(3) . . ?
C18 C19 C20 120.0(3) . . ?
C19 C20 C15 120.6(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
