# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

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

data_mo_fs335a_0m
_database_code_depnum_ccdc_archive 'CCDC 1033193'
_audit_update_record             
;
2014-11-07 deposited with the CCDC.
2015-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H10 N2 O6'
_chemical_formula_sum            'C17 H10 N2 O6'
_chemical_formula_weight         338.27

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'
O O 0.0106 0.0060 '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'

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

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

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

_cell_length_a                   8.2271(12)
_cell_length_b                   13.429(2)
_cell_length_c                   13.894(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.830(3)
_cell_angle_gamma                90
_cell_volume                     1502.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2633
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      25.45
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.351
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.168
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'

_exptl_special_details           
; 

;

_diffrn_ambient_temperature      294(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 SMART APEX II DUO CCD area-detector diffractometer 
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?

_diffrn_reflns_number            7157
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.131
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2742
_reflns_number_gt                1997
_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, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

_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)+(0.0639P)²+0.2871P] 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         2742
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1257
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

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 0.17514(18) 0.78404(10) -0.00598(11) 0.0556(4) Uani 1 1 d . . . . .
O2 O 0.3765(2) 0.34821(13) -0.08291(14) 0.0788(5) Uani 1 1 d . . . . .
O3 O 0.2325(3) 0.32272(12) 0.02804(13) 0.0828(6) Uani 1 1 d . . . . .
O4 O 0.2281(2) 0.73415(14) 0.19104(13) 0.0881(6) Uani 1 1 d . . . . .
O5 O 0.0254(2) 0.63239(13) 0.17614(11) 0.0686(5) Uani 1 1 d . . . . .
O6 O -0.13911(19) 0.97955(15) -0.14338(16) 0.0901(6) Uani 1 1 d . . . . .
N1 N 0.2915(2) 0.37702(14) -0.02587(14) 0.0577(5) Uani 1 1 d . . . . .
N2 N 0.1448(2) 0.66746(13) 0.14951(11) 0.0476(4) Uani 1 1 d . . . . .
C1 C 0.1449(2) 0.93040(13) -0.10275(12) 0.0389(4) Uani 1 1 d . . . . .
C2 C 0.2178(2) 1.01001(13) -0.14865(12) 0.0374(4) Uani 1 1 d . . . . .
C3 C 0.1296(2) 1.09389(15) -0.19236(15) 0.0498(5) Uani 1 1 d . . . . .
H3A H 0.0167 1.0994 -0.1931 0.060 Uiso 1 1 calc R U . . .
C4 C 0.2077(3) 1.16699(15) -0.23349(16) 0.0578(5) Uani 1 1 d . . . . .
H4A H 0.1468 1.2216 -0.2620 0.069 Uiso 1 1 calc R U . . .
C5 C 0.3763(3) 1.16181(16) -0.23375(16) 0.0568(5) Uani 1 1 d . . . . .
H5A H 0.4274 1.2125 -0.2623 0.068 Uiso 1 1 calc R U . . .
C6 C 0.4658(2) 1.08263(15) -0.19223(15) 0.0517(5) Uani 1 1 d . . . . .
H6A H 0.5787 1.0793 -0.1924 0.062 Uiso 1 1 calc R U . . .
C7 C 0.3905(2) 1.00525(14) -0.14889(13) 0.0412(4) Uani 1 1 d . . . . .
C8 C 0.4852(2) 0.92446(15) -0.10190(15) 0.0501(5) Uani 1 1 d . . . . .
H8A H 0.5978 0.9212 -0.1027 0.060 Uiso 1 1 calc R U . . .
C9 C 0.4164(2) 0.85177(15) -0.05582(14) 0.0503(5) Uani 1 1 d . . . . .
H9A H 0.4813 0.8004 -0.0235 0.060 Uiso 1 1 calc R U . . .
C10 C 0.2465(2) 0.85539(13) -0.05780(13) 0.0423(4) Uani 1 1 d . . . . .
C11 C 0.2104(2) 0.68562(14) -0.01464(13) 0.0427(4) Uani 1 1 d . . . . .
C12 C 0.2518(3) 0.64367(15) -0.09713(14) 0.0521(5) Uani 1 1 d . . . . .
H12A H 0.2611 0.6836 -0.1504 0.062 Uiso 1 1 calc R U . . .
C13 C 0.2792(3) 0.54261(16) -0.10037(15) 0.0524(5) Uani 1 1 d . . . . .
H13A H 0.3106 0.5142 -0.1549 0.063 Uiso 1 1 calc R U . . .
C14 C 0.2599(2) 0.48434(14) -0.02255(14) 0.0447(5) Uani 1 1 d . . . . .
C15 C 0.2114(2) 0.52268(14) 0.05864(13) 0.0445(5) Uani 1 1 d . . . . .
H15A H 0.1934 0.4817 0.1094 0.053 Uiso 1 1 calc R U . . .
C16 C 0.1905(2) 0.62426(14) 0.06217(12) 0.0399(4) Uani 1 1 d . . . . .
C17 C -0.0343(3) 0.92332(17) -0.10476(16) 0.0546(5) Uani 1 1 d . . . . .
H17A H -0.0691 0.8692 -0.0724 0.065 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 C11 1.364(2) . ?
O1 C10 1.398(2) . ?
O2 N1 1.222(2) . ?
O3 N1 1.215(2) . ?
O4 N2 1.201(2) . ?
O5 N2 1.213(2) . ?
O6 C17 1.188(3) . ?
N1 C14 1.467(3) . ?
N2 C16 1.462(2) . ?
C1 C10 1.375(3) . ?
C1 C2 1.438(2) . ?
C1 C17 1.472(3) . ?
C2 C3 1.408(3) . ?
C2 C7 1.423(2) . ?
C3 C4 1.361(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.390(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.353(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.407(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.415(3) . ?
C8 C9 1.353(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.393(3) . ?
C9 H9A 0.9300 . ?
C11 C12 1.381(3) . ?
C11 C16 1.384(3) . ?
C12 C13 1.378(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.370(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.371(3) . ?
C15 C16 1.377(3) . ?
C15 H15A 0.9300 . ?
C17 H17A 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
C11 O1 C10 119.95(14) . . ?
O3 N1 O2 124.3(2) . . ?
O3 N1 C14 118.30(19) . . ?
O2 N1 C14 117.4(2) . . ?
O4 N2 O5 124.11(17) . . ?
O4 N2 C16 118.42(17) . . ?
O5 N2 C16 117.46(17) . . ?
C10 C1 C2 118.44(15) . . ?
C10 C1 C17 118.35(17) . . ?
C2 C1 C17 123.17(17) . . ?
C3 C2 C7 117.46(17) . . ?
C3 C2 C1 124.15(16) . . ?
C7 C2 C1 118.38(16) . . ?
C4 C3 C2 120.83(18) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 H4A 119.3 . . ?
C5 C4 H4A 119.3 . . ?
C6 C5 C4 119.63(19) . . ?
C6 C5 H5A 120.2 . . ?
C4 C5 H5A 120.2 . . ?
C5 C6 C7 120.93(19) . . ?
C5 C6 H6A 119.5 . . ?
C7 C6 H6A 119.5 . . ?
C6 C7 C8 120.99(17) . . ?
C6 C7 C2 119.69(17) . . ?
C8 C7 C2 119.27(17) . . ?
C9 C8 C7 121.83(17) . . ?
C9 C8 H8A 119.1 . . ?
C7 C8 H8A 119.1 . . ?
C8 C9 C10 118.73(18) . . ?
C8 C9 H9A 120.6 . . ?
C10 C9 H9A 120.6 . . ?
C1 C10 C9 123.29(17) . . ?
C1 C10 O1 117.10(16) . . ?
C9 C10 O1 119.44(17) . . ?
O1 C11 C12 124.18(17) . . ?
O1 C11 C16 116.61(16) . . ?
C12 C11 C16 119.03(18) . . ?
C13 C12 C11 119.92(18) . . ?
C13 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C14 C13 C12 119.37(18) . . ?
C14 C13 H13A 120.3 . . ?
C12 C13 H13A 120.3 . . ?
C13 C14 C15 122.35(19) . . ?
C13 C14 N1 119.09(18) . . ?
C15 C14 N1 118.56(18) . . ?
C14 C15 C16 117.43(18) . . ?
C14 C15 H15A 121.3 . . ?
C16 C15 H15A 121.3 . . ?
C15 C16 C11 121.79(17) . . ?
C15 C16 N2 118.55(16) . . ?
C11 C16 N2 119.66(17) . . ?
O6 C17 C1 126.8(2) . . ?
O6 C17 H17A 116.6 . . ?
C1 C17 H17A 116.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 -176.37(17) . . . . ?
C17 C1 C2 C3 6.0(3) . . . . ?
C10 C1 C2 C7 2.5(2) . . . . ?
C17 C1 C2 C7 -175.07(17) . . . . ?
C7 C2 C3 C4 0.3(3) . . . . ?
C1 C2 C3 C4 179.23(18) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C5 C6 C7 C8 -177.38(19) . . . . ?
C5 C6 C7 C2 0.1(3) . . . . ?
C3 C2 C7 C6 -0.3(3) . . . . ?
C1 C2 C7 C6 -179.26(16) . . . . ?
C3 C2 C7 C8 177.22(17) . . . . ?
C1 C2 C7 C8 -1.8(2) . . . . ?
C6 C7 C8 C9 176.86(18) . . . . ?
C2 C7 C8 C9 -0.6(3) . . . . ?
C7 C8 C9 C10 2.1(3) . . . . ?
C2 C1 C10 C9 -1.1(3) . . . . ?
C17 C1 C10 C9 176.67(18) . . . . ?
C2 C1 C10 O1 174.19(15) . . . . ?
C17 C1 C10 O1 -8.1(2) . . . . ?
C8 C9 C10 C1 -1.3(3) . . . . ?
C8 C9 C10 O1 -176.45(17) . . . . ?
C11 O1 C10 C1 136.92(18) . . . . ?
C11 O1 C10 C9 -47.6(2) . . . . ?
C10 O1 C11 C12 -28.6(3) . . . . ?
C10 O1 C11 C16 156.40(17) . . . . ?
O1 C11 C12 C13 -177.51(19) . . . . ?
C16 C11 C12 C13 -2.6(3) . . . . ?
C11 C12 C13 C14 2.1(3) . . . . ?
C12 C13 C14 C15 1.0(3) . . . . ?
C12 C13 C14 N1 -179.14(17) . . . . ?
O3 N1 C14 C13 -160.23(19) . . . . ?
O2 N1 C14 C13 19.9(3) . . . . ?
O3 N1 C14 C15 19.6(3) . . . . ?
O2 N1 C14 C15 -160.19(18) . . . . ?
C13 C14 C15 C16 -3.3(3) . . . . ?
N1 C14 C15 C16 176.82(16) . . . . ?
C14 C15 C16 C11 2.7(3) . . . . ?
C14 C15 C16 N2 -177.81(16) . . . . ?
O1 C11 C16 C15 175.48(16) . . . . ?
C12 C11 C16 C15 0.2(3) . . . . ?
O1 C11 C16 N2 -4.0(3) . . . . ?
C12 C11 C16 N2 -179.27(17) . . . . ?
O4 N2 C16 C15 127.0(2) . . . . ?
O5 N2 C16 C15 -52.1(2) . . . . ?
O4 N2 C16 C11 -53.5(2) . . . . ?
O5 N2 C16 C11 127.47(19) . . . . ?
C10 C1 C17 O6 -177.1(2) . . . . ?
C2 C1 C17 O6 0.5(3) . . . . ?

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.037

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag

C3 H3A O6 0.9300 2.2500 2.885(3) 125.00 . yes
C8 H8A O6 0.9300 2.4700 3.341(2) 155.00 1_655 yes
C12 H12A O4 0.9300 2.4300 3.340(3) 166.00 4_575 yes

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_mo_fs394_0m
_database_code_depnum_ccdc_archive 'CCDC 1045108'
_audit_update_record             
;
2015-01-23 deposited with the CCDC.
2015-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H10 N2 O5'
_chemical_formula_sum            'C16 H10 N2 O5'
_chemical_formula_weight         310.26

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

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

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

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

_cell_length_a                   21.9055(19)
_cell_length_b                   4.6272(4)
_cell_length_c                   13.7499(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.655(2)
_cell_angle_gamma                90
_cell_volume                     1392.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    3742
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      24.52

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.624
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.074
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'

_exptl_special_details           
; 
?
;

_diffrn_ambient_temperature      294(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 SMART APEX II DUO CCD area-detector diffractometer 
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18679
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.861
_diffrn_reflns_theta_max         26.557
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2898
_reflns_number_gt                1973
_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, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

_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)+(0.0716P)²+0.5549P] 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         2898
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1603
_refine_ls_wR_factor_gt          0.1392
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

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 0.75787(7) 0.6806(4) 0.35461(11) 0.0600(5) Uani 1 1 d . . . . .
O2 O 0.73497(9) 0.2689(4) 0.47615(13) 0.0728(5) Uani 1 1 d . . . . .
O3 O 0.66476(9) 0.3711(5) 0.57281(13) 0.0905(7) Uani 1 1 d . . . . .
O4 O 0.47982(8) 0.7763(5) 0.42655(15) 0.0824(6) Uani 1 1 d . . . . .
O5 O 0.48883(9) 1.1272(5) 0.32690(15) 0.0886(7) Uani 1 1 d . . . . .
N1 N 0.69003(9) 0.4042(4) 0.49687(13) 0.0539(5) Uani 1 1 d . . . . .
N2 N 0.51005(9) 0.9278(5) 0.37446(14) 0.0599(5) Uani 1 1 d . . . . .
C1 C 0.77790(11) 0.6526(6) 0.18344(17) 0.0584(6) Uani 1 1 d . . . . .
H1A H 0.7467 0.5174 0.1748 0.070 Uiso 1 1 calc R U . . .
C2 C 0.81197(11) 0.7318(6) 0.10725(17) 0.0591(6) Uani 1 1 d . . . . .
H2A H 0.8040 0.6514 0.0460 0.071 Uiso 1 1 calc R U . . .
C3 C 0.85877(10) 0.9334(5) 0.12151(17) 0.0532(6) Uani 1 1 d . . . . .
C4 C 0.89528(12) 1.0201(6) 0.0415(2) 0.0710(7) Uani 1 1 d . . . . .
H4A H 0.8871 0.9433 -0.0202 0.085 Uiso 1 1 calc R U . . .
C5 C 0.94089(13) 1.2109(7) 0.0561(2) 0.0804(9) Uani 1 1 d . . . . .
H5A H 0.9645 1.2646 0.0045 0.096 Uiso 1 1 calc R U . . .
C6 C 0.95308(13) 1.3297(7) 0.1488(2) 0.0841(9) Uani 1 1 d . . . . .
H6A H 0.9851 1.4606 0.1579 0.101 Uiso 1 1 calc R U . . .
C7 C 0.91932(11) 1.2583(6) 0.2259(2) 0.0708(7) Uani 1 1 d . . . . .
H7A H 0.9275 1.3426 0.2865 0.085 Uiso 1 1 calc R U . . .
C8 C 0.87242(10) 1.0574(5) 0.21271(17) 0.0543(6) Uani 1 1 d . . . . .
C9 C 0.83500(10) 0.9719(6) 0.29221(17) 0.0578(6) Uani 1 1 d . . . . .
H9A H 0.8419 1.0509 0.3539 0.069 Uiso 1 1 calc R U . . .
C10 C 0.79063(10) 0.7786(5) 0.27554(16) 0.0531(6) Uani 1 1 d . . . . .
C11 C 0.69767(9) 0.7397(5) 0.35580(14) 0.0472(5) Uani 1 1 d . . . . .
C12 C 0.66307(9) 0.6139(5) 0.42746(13) 0.0447(5) Uani 1 1 d . . . . .
C13 C 0.60201(10) 0.6758(5) 0.43487(14) 0.0481(5) Uani 1 1 d . . . . .
H13A H 0.5795 0.5909 0.4830 0.058 Uiso 1 1 calc R U . . .
C14 C 0.57511(9) 0.8663(5) 0.36933(15) 0.0488(5) Uani 1 1 d . . . . .
C15 C 0.60788(10) 0.9950(5) 0.29813(15) 0.0523(5) Uani 1 1 d . . . . .
H15A H 0.5888 1.1229 0.2543 0.063 Uiso 1 1 calc R U . . .
C16 C 0.66857(10) 0.9340(5) 0.29208(15) 0.0533(6) Uani 1 1 d . . . . .
H16A H 0.6908 1.0238 0.2446 0.064 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 C11 1.348(3) . ?
O1 C10 1.405(2) . ?
O2 N1 1.212(2) . ?
O3 N1 1.214(2) . ?
O4 N2 1.219(3) . ?
O5 N2 1.211(3) . ?
N1 C12 1.466(3) . ?
N2 C14 1.458(3) . ?
C1 C2 1.364(3) . ?
C1 C10 1.410(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.393(3) . ?
C2 H2A 0.9300 . ?
C3 C8 1.399(3) . ?
C3 C4 1.447(3) . ?
C4 C5 1.341(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.403(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.360(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.391(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.451(3) . ?
C9 C10 1.333(3) . ?
C9 H9A 0.9300 . ?
C11 C16 1.389(3) . ?
C11 C12 1.398(3) . ?
C12 C13 1.376(3) . ?
C13 C14 1.374(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.376(3) . ?
C15 C16 1.366(3) . ?
C15 H15A 0.9300 . ?
C16 H16A 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
C11 O1 C10 118.61(16) . . ?
O2 N1 O3 123.0(2) . . ?
O2 N1 C12 119.73(18) . . ?
O3 N1 C12 117.2(2) . . ?
O5 N2 O4 123.4(2) . . ?
O5 N2 C14 118.3(2) . . ?
O4 N2 C14 118.3(2) . . ?
C2 C1 C10 119.1(2) . . ?
C2 C1 H1A 120.5 . . ?
C10 C1 H1A 120.5 . . ?
C1 C2 C3 119.8(2) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
C2 C3 C8 121.7(2) . . ?
C2 C3 C4 120.5(2) . . ?
C8 C3 C4 117.7(2) . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C7 C6 C5 121.7(3) . . ?
C7 C6 H6A 119.2 . . ?
C5 C6 H6A 119.2 . . ?
C6 C7 C8 119.1(3) . . ?
C6 C7 H7A 120.5 . . ?
C8 C7 H7A 120.5 . . ?
C7 C8 C3 121.1(2) . . ?
C7 C8 C9 121.6(2) . . ?
C3 C8 C9 117.3(2) . . ?
C10 C9 C8 119.1(2) . . ?
C10 C9 H9A 120.5 . . ?
C8 C9 H9A 120.5 . . ?
C9 C10 O1 118.6(2) . . ?
C9 C10 C1 123.0(2) . . ?
O1 C10 C1 118.3(2) . . ?
O1 C11 C16 122.98(18) . . ?
O1 C11 C12 119.12(19) . . ?
C16 C11 C12 117.80(19) . . ?
C13 C12 C11 121.74(19) . . ?
C13 C12 N1 116.94(18) . . ?
C11 C12 N1 121.31(19) . . ?
C14 C13 C12 118.28(19) . . ?
C14 C13 H13A 120.9 . . ?
C12 C13 H13A 120.9 . . ?
C13 C14 C15 121.5(2) . . ?
C13 C14 N2 118.94(19) . . ?
C15 C14 N2 119.6(2) . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 H15A 120.2 . . ?
C14 C15 H15A 120.2 . . ?
C15 C16 C11 121.0(2) . . ?
C15 C16 H16A 119.5 . . ?
C11 C16 H16A 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 0.4(4) . . . . ?
C1 C2 C3 C8 0.5(4) . . . . ?
C1 C2 C3 C4 -179.9(2) . . . . ?
C2 C3 C4 C5 -178.9(3) . . . . ?
C8 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C4 C5 C6 C7 -0.5(5) . . . . ?
C5 C6 C7 C8 1.5(5) . . . . ?
C6 C7 C8 C3 -1.4(4) . . . . ?
C6 C7 C8 C9 179.8(2) . . . . ?
C2 C3 C8 C7 179.9(2) . . . . ?
C4 C3 C8 C7 0.3(4) . . . . ?
C2 C3 C8 C9 -1.2(3) . . . . ?
C4 C3 C8 C9 179.2(2) . . . . ?
C7 C8 C9 C10 180.0(2) . . . . ?
C3 C8 C9 C10 1.1(3) . . . . ?
C8 C9 C10 O1 175.06(19) . . . . ?
C8 C9 C10 C1 -0.3(4) . . . . ?
C11 O1 C10 C9 116.1(2) . . . . ?
C11 O1 C10 C1 -68.4(3) . . . . ?
C2 C1 C10 C9 -0.4(4) . . . . ?
C2 C1 C10 O1 -175.8(2) . . . . ?
C10 O1 C11 C16 -11.5(3) . . . . ?
C10 O1 C11 C12 172.2(2) . . . . ?
O1 C11 C12 C13 177.19(19) . . . . ?
C16 C11 C12 C13 0.7(3) . . . . ?
O1 C11 C12 N1 -4.2(3) . . . . ?
C16 C11 C12 N1 179.3(2) . . . . ?
O2 N1 C12 C13 155.3(2) . . . . ?
O3 N1 C12 C13 -23.3(3) . . . . ?
O2 N1 C12 C11 -23.3(3) . . . . ?
O3 N1 C12 C11 158.1(2) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
N1 C12 C13 C14 -178.47(19) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C12 C13 C14 N2 178.25(19) . . . . ?
O5 N2 C14 C13 168.8(2) . . . . ?
O4 N2 C14 C13 -11.0(3) . . . . ?
O5 N2 C14 C15 -12.5(3) . . . . ?
O4 N2 C14 C15 167.7(2) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
N2 C14 C15 C16 -178.9(2) . . . . ?
C14 C15 C16 C11 1.1(4) . . . . ?
O1 C11 C16 C15 -177.7(2) . . . . ?
C12 C11 C16 C15 -1.3(3) . . . . ?

_refine_diff_density_max         0.401
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.042

_shelxl_version_number           2014-3


loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag

C13 H13A O4 0.9300 2.5000 3.397(3) 161.00 3_666 yes
C16 H16A O3 0.9300 2.4500 3.144(3) 131.00 4_575 yes

