# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_bmk4553
_database_code_depnum_ccdc_archive 'CCDC 1568068'
_audit_update_record             
;
2017-08-10 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C25 H15 Br2 N O2'
_chemical_formula_sum            'C25 H15 Br2 N O2'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         521.20

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   9.2108(6)
_cell_length_b                   11.4244(6)
_cell_length_c                   11.4731(7)
_cell_angle_alpha                68.214(2)
_cell_angle_beta                 87.658(2)
_cell_angle_gamma                69.9597(19)
_cell_volume                     1048.01(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9968
_cell_measurement_theta_min      3.192
_cell_measurement_theta_max      26.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.590
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    3.890
_shelx_estimated_absorpt_T_min   0.207
_shelx_estimated_absorpt_T_max   0.525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4600
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19733
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.192
_diffrn_reflns_theta_max         26.410
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4268
_reflns_number_gt                3444
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0708P)²+7.7818P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4268
_refine_ls_number_parameters     269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0663
_refine_ls_wR_factor_ref         0.1708
_refine_ls_wR_factor_gt          0.1603
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.75215(8) 0.38002(7) 0.82505(7) 0.0354(2) Uani 0.9478(17) 1 d . . P A 1
Br1' Br 0.6890(16) 0.4363(13) 0.7448(14) 0.0354(2) Uani 0.0522(17) 1 d . . P A
2
Br2 Br 0.18158(8) 0.47864(7) 0.61344(7) 0.0343(2) Uani 1 1 d . . . . .
O1 O 0.4995(4) 0.9062(4) 0.1650(3) 0.0158(8) Uani 1 1 d . . . . .
O2 O 0.2625(4) 0.9019(4) 0.1857(4) 0.0200(8) Uani 1 1 d . . . . .
N N 0.2920(5) 0.8153(5) 0.4418(4) 0.0153(9) Uani 1 1 d . . . . .
C1 C 0.6427(6) 0.8899(5) 0.2153(5) 0.0129(10) Uani 1 1 d . . . . .
C2 C 0.7494(6) 0.9155(6) 0.1288(5) 0.0184(11) Uani 1 1 d . . . . .
H2A H 0.7229 0.9435 0.0411 0.022 Uiso 1 1 calc R U . . .
C3 C 0.8947(6) 0.8992(6) 0.1739(5) 0.0198(12) Uani 1 1 d . . . . .
H3A H 0.9692 0.9165 0.1166 0.024 Uiso 1 1 calc R U . . .
C4 C 0.9327(6) 0.8576(6) 0.3029(5) 0.0186(11) Uani 1 1 d . . . . .
H4A H 1.0328 0.8467 0.3333 0.022 Uiso 1 1 calc R U . . .
C5 C 0.8252(6) 0.8325(5) 0.3859(5) 0.0168(11) Uani 1 1 d . . . . .
H5A H 0.8526 0.8034 0.4736 0.020 Uiso 1 1 calc R U . . .
C6 C 0.6759(6) 0.8486(5) 0.3443(5) 0.0122(10) Uani 1 1 d . . . . .
C7 C 0.5595(6) 0.8154(5) 0.4286(5) 0.0129(10) Uani 1 1 d . . . . .
C8 C 0.5942(6) 0.7737(6) 0.5626(5) 0.0170(11) Uani 1 1 d . . . . .
H8A H 0.6544 0.8135 0.5897 0.020 Uiso 1 1 calc R U . . .
C9 C 0.5470(6) 0.6825(6) 0.6514(5) 0.0192(11) Uani 1 1 d . . . . .
C10 C 0.4605(6) 0.6108(6) 0.6098(6) 0.0207(12) Uani 1 1 d . . . . .
H10A H 0.4457 0.5366 0.6827 0.025 Uiso 1 1 calc R U . . .
H10B H 0.5159 0.5743 0.5481 0.025 Uiso 1 1 calc R U . . .
C11 C 0.3050(6) 0.7237(6) 0.5491(5) 0.0167(11) Uani 1 1 d . . . . .
C12 C 0.4202(6) 0.8288(5) 0.3771(5) 0.0113(10) Uani 1 1 d . . . . .
C13 C 0.3850(6) 0.8809(5) 0.2380(5) 0.0149(11) Uani 1 1 d . . . . .
C14 C 0.5734(6) 0.6546(6) 0.7876(5) 0.0175(11) Uani 1 1 d . . . . .
C15 C 0.5098(6) 0.7681(6) 0.8312(5) 0.0217(12) Uani 1 1 d . . . . .
H15A H 0.4481 0.8558 0.7750 0.026 Uiso 1 1 calc R U . . .
C16 C 0.5430(8) 0.7416(7) 0.9525(7) 0.0335(16) Uani 1 1 d . . . . .
H16A H 0.5026 0.8125 0.9825 0.040 Uiso 1 1 calc R U . . .
C17 C 0.6353(8) 0.6131(7) 1.0381(6) 0.0313(15) Uani 1 1 d . . . . .
H17A H 0.6575 0.5999 1.1231 0.038 Uiso 1 1 calc R U . . .
C18 C 0.6935(7) 0.5070(6) 1.0001(5) 0.0256(13) Uani 1 1 d . . . . .
H18A H 0.7549 0.4203 1.0582 0.031 Uiso 1 1 calc R U . . .
C19 C 0.6613(7) 0.5283(6) 0.8754(6) 0.0241(13) Uani 1 1 d . . . . .
C20 C 0.1702(6) 0.7262(6) 0.6250(5) 0.0169(11) Uani 1 1 d . . . . .
C21 C 0.1027(7) 0.8381(6) 0.6583(6) 0.0267(13) Uani 1 1 d . . . . .
H21A H 0.1446 0.9081 0.6291 0.032 Uiso 1 1 calc R U . . .
C22 C -0.0156(6) 0.8527(7) 0.7280(6) 0.0265(10) Uani 1 1 d . . . . .
H22A H -0.0621 0.9327 0.7440 0.032 Uiso 1 1 calc R U . . .
C23 C -0.0723(6) 0.7374(6) 0.7800(6) 0.0265(10) Uani 1 1 d . . . . .
H23A H -0.1502 0.7391 0.8368 0.032 Uiso 1 1 calc R U . . .
C24 C -0.0108(6) 0.6279(6) 0.7449(6) 0.0230(12) Uani 1 1 d . . . . .
H24A H -0.0496 0.5559 0.7734 0.028 Uiso 1 1 calc R U . . .
C25 C 0.1088(6) 0.6255(6) 0.6673(5) 0.0187(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C19 1.902(6) . ?
Br1' C19 2.090(15) . ?
Br2 C25 1.900(6) . ?
O1 C13 1.362(6) . ?
O1 C1 1.386(6) . ?
O2 C13 1.206(6) . ?
N C11 1.263(7) . ?
N C12 1.391(6) . ?
C1 C6 1.388(7) . ?
C1 C2 1.392(7) . ?
C2 C3 1.381(8) . ?
C2 H2A 0.9500 . ?
C3 C4 1.395(8) . ?
C3 H3A 0.9500 . ?
C4 C5 1.373(8) . ?
C4 H4A 0.9500 . ?
C5 C6 1.403(7) . ?
C5 H5A 0.9500 . ?
C6 C7 1.466(7) . ?
C7 C12 1.371(7) . ?
C7 C8 1.444(7) . ?
C8 C9 1.342(8) . ?
C8 H8A 0.9500 . ?
C9 C14 1.487(8) . ?
C9 C10 1.517(8) . ?
C10 C11 1.532(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C20 1.486(7) . ?
C12 C13 1.487(7) . ?
C14 C19 1.393(8) . ?
C14 C15 1.487(8) . ?
C15 C16 1.335(9) . ?
C15 H15A 0.9500 . ?
C16 C17 1.409(10) . ?
C16 H16A 0.9500 . ?
C17 C18 1.369(10) . ?
C17 H17A 0.9500 . ?
C18 C19 1.386(9) . ?
C18 H18A 0.9500 . ?
C20 C25 1.375(8) . ?
C20 C21 1.402(8) . ?
C21 C22 1.326(8) . ?
C21 H21A 0.9500 . ?
C22 C23 1.493(9) . ?
C22 H22A 0.9500 . ?
C23 C24 1.385(8) . ?
C23 H23A 0.9500 . ?
C24 C25 1.387(8) . ?
C24 H24A 0.9500 . ?

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
C13 O1 C1 122.6(4) . . ?
C11 N C12 122.2(4) . . ?
O1 C1 C6 121.2(4) . . ?
O1 C1 C2 115.8(4) . . ?
C6 C1 C2 123.0(5) . . ?
C3 C2 C1 118.3(5) . . ?
C3 C2 H2A 120.9 . . ?
C1 C2 H2A 120.9 . . ?
C2 C3 C4 120.5(5) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C5 C4 C3 119.9(5) . . ?
C5 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
C4 C5 C6 121.6(5) . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C1 C6 C5 116.7(5) . . ?
C1 C6 C7 119.0(4) . . ?
C5 C6 C7 124.1(5) . . ?
C12 C7 C6 118.9(5) . . ?
C12 C7 C8 122.4(5) . . ?
C6 C7 C8 118.7(4) . . ?
C9 C8 C7 124.3(5) . . ?
C9 C8 H8A 117.9 . . ?
C7 C8 H8A 117.9 . . ?
C8 C9 C14 121.3(5) . . ?
C8 C9 C10 118.5(5) . . ?
C14 C9 C10 120.2(5) . . ?
C9 C10 C11 102.4(4) . . ?
C9 C10 H10A 111.3 . . ?
C11 C10 H10A 111.3 . . ?
C9 C10 H10B 111.3 . . ?
C11 C10 H10B 111.3 . . ?
H10A C10 H10B 109.2 . . ?
N C11 C20 120.7(5) . . ?
N C11 C10 122.1(5) . . ?
C20 C11 C10 117.2(5) . . ?
C7 C12 N 126.2(5) . . ?
C7 C12 C13 120.7(5) . . ?
N C12 C13 112.6(4) . . ?
O2 C13 O1 117.9(5) . . ?
O2 C13 C12 124.5(5) . . ?
O1 C13 C12 117.5(4) . . ?
C19 C14 C9 123.0(5) . . ?
C19 C14 C15 118.4(5) . . ?
C9 C14 C15 118.6(5) . . ?
C16 C15 C14 117.2(6) . . ?
C16 C15 H15A 121.4 . . ?
C14 C15 H15A 121.4 . . ?
C15 C16 C17 122.8(6) . . ?
C15 C16 H16A 118.6 . . ?
C17 C16 H16A 118.6 . . ?
C18 C17 C16 120.8(6) . . ?
C18 C17 H17A 119.6 . . ?
C16 C17 H17A 119.6 . . ?
C17 C18 C19 118.9(6) . . ?
C17 C18 H18A 120.6 . . ?
C19 C18 H18A 120.6 . . ?
C14 C19 C18 121.9(6) . . ?
C14 C19 Br1 120.6(5) . . ?
C18 C19 Br1 117.4(5) . . ?
C14 C19 Br1' 93.3(6) . . ?
C18 C19 Br1' 144.8(6) . . ?
C25 C20 C21 117.6(5) . . ?
C25 C20 C11 124.8(5) . . ?
C21 C20 C11 117.6(5) . . ?
C22 C21 C20 124.3(6) . . ?
C22 C21 H21A 117.8 . . ?
C20 C21 H21A 117.8 . . ?
C21 C22 C23 116.8(5) . . ?
C21 C22 H22A 121.6 . . ?
C23 C22 H22A 121.6 . . ?
C24 C23 C22 119.6(5) . . ?
C24 C23 H23A 120.2 . . ?
C22 C23 H23A 120.2 . . ?
C23 C24 C25 118.6(5) . . ?
C23 C24 H24A 120.7 . . ?
C25 C24 H24A 120.7 . . ?
C20 C25 C24 122.9(5) . . ?
C20 C25 Br2 119.9(4) . . ?
C24 C25 Br2 117.2(4) . . ?

_refine_diff_density_max         1.872
_refine_diff_density_min         -0.802
_refine_diff_density_rms         0.144

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_h-m   P-1
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_yt095
_database_code_depnum_ccdc_archive 'CCDC 1568069'
_audit_update_record             
;
2017-08-10 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C25 H17 N O2'
_chemical_formula_sum            'C25 H17 N O2'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            brown
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         363.39

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

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   9.2739(8)
_cell_length_b                   10.1856(11)
_cell_length_c                   11.5874(8)
_cell_angle_alpha                97.047(7)
_cell_angle_beta                 107.405(7)
_cell_angle_gamma                115.973(9)
_cell_volume                     896.95(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2240
_cell_measurement_theta_min      3.3680
_cell_measurement_theta_max      28.8870
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97511
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) 
(compiled Dec  3 2012,18:21:49) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8003
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.934
_diffrn_reflns_theta_max         29.240
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4129
_reflns_number_gt                3197
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0472P)²+0.1872P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4129
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.54163(14) 0.00886(12) 0.16386(10) 0.0244(3) Uani 1 1 d . . . . .
O2 O 0.33304(14) 0.03976(13) 0.19194(10) 0.0287(3) Uani 1 1 d . . . . .
N N 0.52864(16) 0.20759(14) 0.44073(11) 0.0185(3) Uani 1 1 d . . . . .
C1 C 0.7071(2) 0.02739(17) 0.20805(14) 0.0198(3) Uani 1 1 d . . . . .
C2 C 0.7571(2) -0.02375(18) 0.11868(15) 0.0255(4) Uani 1 1 d . . . . .
H2A H 0.6786 -0.0713 0.0323 0.031 Uiso 1 1 calc R U . . .
C3 C 0.9231(2) -0.00442(18) 0.15739(15) 0.0259(4) Uani 1 1 d . . . . .
H3A H 0.9596 -0.0375 0.0969 0.031 Uiso 1 1 calc R U . . .
C4 C 1.0374(2) 0.06319(17) 0.28441(15) 0.0246(3) Uani 1 1 d . . . . .
H4A H 1.1505 0.0742 0.3108 0.029 Uiso 1 1 calc R U . . .
C5 C 0.9853(2) 0.11422(17) 0.37200(14) 0.0214(3) Uani 1 1 d . . . . .
H5A H 1.0639 0.1611 0.4584 0.026 Uiso 1 1 calc R U . . .
C6 C 0.81850(19) 0.09798(16) 0.33553(13) 0.0181(3) Uani 1 1 d . . . . .
C7 C 0.76418(19) 0.16566(16) 0.42084(13) 0.0182(3) Uani 1 1 d . . . . .
C8 C 0.88015(19) 0.24059(17) 0.55286(13) 0.0187(3) Uani 1 1 d . . . . .
H8A H 0.9443 0.1964 0.5941 0.022 Uiso 1 1 calc R U . . .
C9 C 0.90161(18) 0.37013(16) 0.62022(13) 0.0173(3) Uani 1 1 d . . . . .
C10 C 0.80962(19) 0.44462(16) 0.54977(13) 0.0183(3) Uani 1 1 d . . . . .
H10A H 0.8244 0.4494 0.4690 0.022 Uiso 1 1 calc R U . . .
H10B H 0.8525 0.5491 0.6016 0.022 Uiso 1 1 calc R U . . .
C11 C 0.62142(19) 0.33802(16) 0.52717(13) 0.0169(3) Uani 1 1 d . . . . .
C12 C 0.60292(19) 0.15570(16) 0.37207(13) 0.0175(3) Uani 1 1 d . . . . .
C13 C 0.4806(2) 0.06547(17) 0.23988(14) 0.0206(3) Uani 1 1 d . . . . .
C14 C 1.00763(19) 0.43624(17) 0.75786(13) 0.0186(3) Uani 1 1 d . . . . .
C15 C 1.0155(2) 0.34131(18) 0.83440(14) 0.0225(3) Uani 1 1 d . . . . .
H15A H 0.9463 0.2334 0.7985 0.027 Uiso 1 1 calc R U . . .
C16 C 1.1234(2) 0.4034(2) 0.96207(15) 0.0277(4) Uani 1 1 d . . . . .
H16A H 1.1284 0.3378 1.0129 0.033 Uiso 1 1 calc R U . . .
C17 C 1.2236(2) 0.5601(2) 1.01601(15) 0.0289(4) Uani 1 1 d . . . . .
H17A H 1.2985 0.6022 1.1033 0.035 Uiso 1 1 calc R U . . .
C18 C 1.2145(2) 0.65553(19) 0.94216(15) 0.0284(4) Uani 1 1 d . . . . .
H18A H 1.2821 0.7633 0.9791 0.034 Uiso 1 1 calc R U . . .
C19 C 1.1071(2) 0.59430(18) 0.81474(14) 0.0239(3) Uani 1 1 d . . . . .
H19A H 1.1008 0.6607 0.7651 0.029 Uiso 1 1 calc R U . . .
C20 C 0.54679(19) 0.38101(16) 0.61194(13) 0.0173(3) Uani 1 1 d . . . . .
C21 C 0.6112(2) 0.53347(17) 0.67435(14) 0.0220(3) Uani 1 1 d . . . . .
H21A H 0.7043 0.6123 0.6623 0.026 Uiso 1 1 calc R U . . .
C22 C 0.5401(2) 0.57106(18) 0.75411(15) 0.0252(4) Uani 1 1 d . . . . .
H22A H 0.5841 0.6753 0.7956 0.030 Uiso 1 1 calc R U . . .
C23 C 0.4058(2) 0.45729(19) 0.77322(15) 0.0255(4) Uani 1 1 d . . . . .
H23A H 0.3589 0.4831 0.8290 0.031 Uiso 1 1 calc R U . . .
C24 C 0.3395(2) 0.30524(18) 0.71089(15) 0.0239(3) Uani 1 1 d . . . . .
H24A H 0.2461 0.2270 0.7233 0.029 Uiso 1 1 calc R U . . .
C25 C 0.40899(19) 0.26709(17) 0.63059(14) 0.0205(3) Uani 1 1 d . . . . .
H25A H 0.3626 0.1628 0.5879 0.025 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.3740(17) . ?
O1 C1 1.3803(18) . ?
O2 C13 1.2025(18) . ?
N C11 1.2904(18) . ?
N C12 1.3894(17) . ?
C1 C6 1.394(2) . ?
C1 C2 1.388(2) . ?
C2 C3 1.382(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.394(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.385(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.402(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.4633(19) . ?
C7 C12 1.383(2) . ?
C7 C8 1.446(2) . ?
C8 C9 1.347(2) . ?
C8 H8A 0.9500 . ?
C9 C14 1.477(2) . ?
C9 C10 1.507(2) . ?
C10 C11 1.513(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C20 1.4840(19) . ?
C12 C13 1.476(2) . ?
C14 C19 1.397(2) . ?
C14 C15 1.400(2) . ?
C15 C16 1.386(2) . ?
C15 H15A 0.9500 . ?
C16 C17 1.382(2) . ?
C16 H16A 0.9500 . ?
C17 C18 1.384(2) . ?
C17 H17A 0.9500 . ?
C18 C19 1.382(2) . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9500 . ?
C20 C21 1.395(2) . ?
C20 C25 1.398(2) . ?
C21 C22 1.390(2) . ?
C21 H21A 0.9500 . ?
C22 C23 1.381(2) . ?
C22 H22A 0.9500 . ?
C23 C24 1.387(2) . ?
C23 H23A 0.9500 . ?
C24 C25 1.386(2) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?

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
C13 O1 C1 122.66(12) . . ?
C11 N C12 120.68(13) . . ?
O1 C1 C6 121.08(13) . . ?
O1 C1 C2 116.55(14) . . ?
C6 C1 C2 122.34(15) . . ?
C3 C2 C1 118.89(15) . . ?
C3 C2 H2A 120.6 . . ?
C1 C2 H2A 120.6 . . ?
C2 C3 C4 120.55(14) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C5 C4 C3 119.65(15) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
C4 C5 C6 121.20(15) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 H5A 119.4 . . ?
C1 C6 C5 117.36(13) . . ?
C1 C6 C7 118.95(13) . . ?
C5 C6 C7 123.33(14) . . ?
C12 C7 C8 122.17(13) . . ?
C12 C7 C6 118.67(13) . . ?
C8 C7 C6 119.16(13) . . ?
C9 C8 C7 123.13(14) . . ?
C9 C8 H8A 118.4 . . ?
C7 C8 H8A 118.4 . . ?
C8 C9 C14 122.02(13) . . ?
C8 C9 C10 117.20(13) . . ?
C14 C9 C10 120.77(13) . . ?
C9 C10 C11 102.04(11) . . ?
C9 C10 H10A 111.4 . . ?
C11 C10 H10A 111.4 . . ?
C9 C10 H10B 111.4 . . ?
C11 C10 H10B 111.4 . . ?
H10A C10 H10B 109.2 . . ?
N C11 C20 119.69(13) . . ?
N C11 C10 121.33(12) . . ?
C20 C11 C10 118.87(13) . . ?
C7 C12 N 125.95(13) . . ?
C7 C12 C13 120.72(13) . . ?
N C12 C13 112.79(13) . . ?
O2 C13 O1 116.95(13) . . ?
O2 C13 C12 125.69(14) . . ?
O1 C13 C12 117.33(13) . . ?
C19 C14 C15 118.12(14) . . ?
C19 C14 C9 121.33(13) . . ?
C15 C14 C9 120.52(14) . . ?
C16 C15 C14 120.53(15) . . ?
C16 C15 H15A 119.7 . . ?
C14 C15 H15A 119.7 . . ?
C15 C16 C17 120.47(15) . . ?
C15 C16 H16A 119.8 . . ?
C17 C16 H16A 119.8 . . ?
C18 C17 C16 119.69(15) . . ?
C18 C17 H17A 120.2 . . ?
C16 C17 H17A 120.2 . . ?
C19 C18 C17 120.13(15) . . ?
C19 C18 H18A 119.9 . . ?
C17 C18 H18A 119.9 . . ?
C18 C19 C14 121.03(15) . . ?
C18 C19 H19A 119.5 . . ?
C14 C19 H19A 119.5 . . ?
C21 C20 C25 118.71(13) . . ?
C21 C20 C11 121.51(13) . . ?
C25 C20 C11 119.78(13) . . ?
C20 C21 C22 120.53(14) . . ?
C20 C21 H21A 119.7 . . ?
C22 C21 H21A 119.7 . . ?
C23 C22 C21 120.19(14) . . ?
C23 C22 H22A 119.9 . . ?
C21 C22 H22A 119.9 . . ?
C22 C23 C24 119.89(14) . . ?
C22 C23 H23A 120.1 . . ?
C24 C23 H23A 120.1 . . ?
C25 C24 C23 120.18(14) . . ?
C25 C24 H24A 119.9 . . ?
C23 C24 H24A 119.9 . . ?
C24 C25 C20 120.50(14) . . ?
C24 C25 H25A 119.8 . . ?
C20 C25 H25A 119.8 . . ?

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.052

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_h-m   P-1
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_bmk4586
_database_code_depnum_ccdc_archive 'CCDC 1568070'
_audit_update_record             
;
2017-08-10 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C21 H13 N O4'
_chemical_formula_sum            'C21 H13 N O4'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            brown
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         343.32

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

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   7.7587(4)
_cell_length_b                   9.5337(5)
_cell_length_c                   11.8411(5)
_cell_angle_alpha                69.6858(15)
_cell_angle_beta                 82.1641(16)
_cell_angle_gamma                76.8271(16)
_cell_volume                     798.21(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9906
_cell_measurement_theta_min      3.171
_cell_measurement_theta_max      27.097
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8854
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27760
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.196
_diffrn_reflns_theta_max         27.155
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3522
_reflns_number_gt                2990
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0502P)²+0.3076P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3522
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1011
_refine_ls_wR_factor_gt          0.0945
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.28925(13) -0.06523(11) 0.86780(8) 0.0282(2) Uani 1 1 d . . . . .
O2 O 0.28207(16) 0.17919(12) 0.82494(9) 0.0374(3) Uani 1 1 d . . . . .
O3 O 0.32189(12) 0.02138(10) 0.24579(8) 0.0254(2) Uani 1 1 d . . . . .
O4 O 0.34020(12) 0.52283(10) 0.43155(8) 0.0266(2) Uani 1 1 d . . . . .
N N 0.28132(13) 0.24577(12) 0.58508(9) 0.0205(2) Uani 1 1 d . . . . .
C1 C 0.30948(17) -0.19178(15) 0.83239(11) 0.0243(3) Uani 1 1 d . . . . .
C2 C 0.31680(18) -0.33034(17) 0.92480(12) 0.0315(3) Uani 1 1 d . . . . .
H2A H 0.3112 -0.3350 1.0066 0.038 Uiso 1 1 calc R U . . .
C3 C 0.33233(19) -0.46132(16) 0.89608(14) 0.0340(3) Uani 1 1 d . . . . .
H3A H 0.3355 -0.5567 0.9586 0.041 Uiso 1 1 calc R U . . .
C4 C 0.34343(18) -0.45444(15) 0.77600(13) 0.0306(3) Uani 1 1 d . . . . .
H4A H 0.3552 -0.5450 0.7566 0.037 Uiso 1 1 calc R U . . .
C5 C 0.33733(16) -0.31532(14) 0.68480(12) 0.0245(3) Uani 1 1 d . . . . .
H5A H 0.3469 -0.3118 0.6031 0.029 Uiso 1 1 calc R U . . .
C6 C 0.31727(15) -0.17931(14) 0.71080(11) 0.0206(3) Uani 1 1 d . . . . .
C7 C 0.29125(15) -0.02740(14) 0.62003(10) 0.0187(2) Uani 1 1 d . . . . .
C8 C 0.28979(16) -0.01238(14) 0.49411(10) 0.0194(3) Uani 1 1 d . . . . .
H8A H 0.3609 -0.0910 0.4667 0.023 Uiso 1 1 calc R U . . .
C9 C 0.19263(15) 0.10756(14) 0.41338(10) 0.0188(3) Uani 1 1 d . . . . .
C10 C 0.07083(16) 0.22894(14) 0.45616(11) 0.0202(3) Uani 1 1 d . . . . .
H10A H -0.0061 0.1830 0.5270 0.024 Uiso 1 1 calc R U . . .
H10B H -0.0049 0.3010 0.3913 0.024 Uiso 1 1 calc R U . . .
C11 C 0.19340(16) 0.30884(14) 0.48947(11) 0.0196(3) Uani 1 1 d . . . . .
C12 C 0.27659(16) 0.09695(14) 0.65757(10) 0.0199(3) Uani 1 1 d . . . . .
C13 C 0.28382(18) 0.07789(15) 0.78604(11) 0.0251(3) Uani 1 1 d . . . . .
C14 C 0.20047(16) 0.12635(14) 0.28614(11) 0.0203(3) Uani 1 1 d . . . . .
C15 C 0.10646(18) 0.22803(16) 0.19292(11) 0.0260(3) Uani 1 1 d . . . . .
H15A H 0.0154 0.3123 0.1962 0.031 Uiso 1 1 calc R U . . .
C16 C 0.17067(19) 0.18402(17) 0.08932(12) 0.0297(3) Uani 1 1 d . . . . .
H16A H 0.1305 0.2329 0.0102 0.036 Uiso 1 1 calc R U . . .
C17 C 0.29889(19) 0.06022(16) 0.12516(11) 0.0288(3) Uani 1 1 d . . . . .
H17A H 0.3649 0.0066 0.0740 0.035 Uiso 1 1 calc R U . . .
C18 C 0.21143(16) 0.45989(14) 0.40973(11) 0.0214(3) Uani 1 1 d . . . . .
C19 C 0.11943(18) 0.56046(15) 0.31466(12) 0.0283(3) Uani 1 1 d . . . . .
H19A H 0.0233 0.5454 0.2813 0.034 Uiso 1 1 calc R U . . .
C20 C 0.1966(2) 0.69300(16) 0.27541(13) 0.0328(3) Uani 1 1 d . . . . .
H20A H 0.1615 0.7841 0.2107 0.039 Uiso 1 1 calc R U . . .
C21 C 0.32861(19) 0.66397(15) 0.34764(13) 0.0306(3) Uani 1 1 d . . . . .
H21A H 0.4037 0.7328 0.3410 0.037 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.3669(16) . ?
O1 C1 1.3795(16) . ?
O2 C13 1.2025(16) . ?
O3 C14 1.3773(15) . ?
O3 C17 1.3716(15) . ?
O4 C18 1.3697(15) . ?
O4 C21 1.3590(16) . ?
N C11 1.2883(16) . ?
N C12 1.3859(16) . ?
C1 C2 1.3873(18) . ?
C1 C6 1.3969(18) . ?
C2 C3 1.380(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.392(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.3850(19) . ?
C4 H4A 0.9500 . ?
C5 C6 1.4045(18) . ?
C5 H5A 0.9500 . ?
C6 C7 1.4623(17) . ?
C7 C12 1.3808(17) . ?
C7 C8 1.4489(16) . ?
C8 C9 1.3543(17) . ?
C8 H8A 0.9500 . ?
C9 C14 1.4486(16) . ?
C9 C10 1.5056(16) . ?
C10 C11 1.5104(16) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C18 1.4480(17) . ?
C12 C13 1.4755(17) . ?
C14 C15 1.3580(18) . ?
C15 C16 1.4229(19) . ?
C15 H15A 0.9500 . ?
C16 C17 1.340(2) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 C19 1.3616(18) . ?
C19 C20 1.426(2) . ?
C19 H19A 0.9500 . ?
C20 C21 1.342(2) . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9500 . ?

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
C13 O1 C1 121.95(10) . . ?
C14 O3 C17 106.19(10) . . ?
C18 O4 C21 106.54(10) . . ?
C11 N C12 121.08(10) . . ?
C2 C1 O1 115.87(12) . . ?
C2 C1 C6 122.54(13) . . ?
O1 C1 C6 121.57(11) . . ?
C1 C2 C3 119.02(13) . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 H2A 120.5 . . ?
C2 C3 C4 120.35(13) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C5 C4 C3 119.90(13) . . ?
C5 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
C4 C5 C6 121.29(13) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 H5A 119.4 . . ?
C1 C6 C5 116.88(11) . . ?
C1 C6 C7 118.81(11) . . ?
C5 C6 C7 124.14(11) . . ?
C12 C7 C8 122.25(11) . . ?
C12 C7 C6 118.24(11) . . ?
C8 C7 C6 119.44(11) . . ?
C9 C8 C7 123.58(11) . . ?
C9 C8 H8A 118.2 . . ?
C7 C8 H8A 118.2 . . ?
C8 C9 C14 123.18(11) . . ?
C8 C9 C10 119.19(11) . . ?
C14 C9 C10 117.63(11) . . ?
C9 C10 C11 104.69(9) . . ?
C9 C10 H10A 110.8 . . ?
C11 C10 H10A 110.8 . . ?
C9 C10 H10B 110.8 . . ?
C11 C10 H10B 110.8 . . ?
H10A C10 H10B 108.9 . . ?
N C11 C18 120.18(11) . . ?
N C11 C10 121.82(11) . . ?
C18 C11 C10 118.00(10) . . ?
N C12 C7 126.96(11) . . ?
N C12 C13 111.23(10) . . ?
C7 C12 C13 121.09(11) . . ?
O2 C13 O1 117.21(11) . . ?
O2 C13 C12 125.05(12) . . ?
O1 C13 C12 117.72(11) . . ?
C15 C14 O3 109.59(11) . . ?
C15 C14 C9 132.97(12) . . ?
O3 C14 C9 117.41(11) . . ?
C14 C15 C16 106.80(12) . . ?
C14 C15 H15A 126.6 . . ?
C16 C15 H15A 126.6 . . ?
C17 C16 C15 106.59(12) . . ?
C17 C16 H16A 126.7 . . ?
C15 C16 H16A 126.7 . . ?
C16 C17 O3 110.82(12) . . ?
C16 C17 H17A 124.6 . . ?
O3 C17 H17A 124.6 . . ?
O4 C18 C19 109.91(11) . . ?
O4 C18 C11 117.50(11) . . ?
C19 C18 C11 132.56(12) . . ?
C18 C19 C20 106.07(12) . . ?
C18 C19 H19A 127.0 . . ?
C20 C19 H19A 127.0 . . ?
C21 C20 C19 106.64(12) . . ?
C21 C20 H20A 126.7 . . ?
C19 C20 H20A 126.7 . . ?
C20 C21 O4 110.83(12) . . ?
C20 C21 H21A 124.6 . . ?
O4 C21 H21A 124.6 . . ?

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.045

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_h-m   P-1
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

