# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

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

data_mo_af115_0m
_database_code_depnum_ccdc_archive 'CCDC 1053544'
_audit_update_record             
;
2015-03-12 deposited with the CCDC.
2015-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 N4 O4'
_chemical_formula_weight         304.31

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   8.1008(19)
_cell_length_b                   9.745(2)
_cell_length_c                   18.180(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1435.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6479
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      36.27

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9690
_exptl_absorpt_correction_T_max  0.9792
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_suppport 
'magnetic support whith 10 micron nylon fiber cryoloop'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_source_type              'Bruker-Nonius FR 591'
_diffrn_source_power             50
_diffrn_source_current           70
_diffrn_source_size              '3 mm x 0.3 mm fine focus'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            17453
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         36.57
_reflns_number_total             7016
_reflns_number_gt                6050
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 v2009.1-0'
_computing_cell_refinement       'Bruker APEX2 v2009.1-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)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    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_chemical_absolute_configuration ad
_refine_ls_abs_structure_Flack   -0.4(6)
_refine_ls_number_reflns         7016
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1420
_refine_ls_wR_factor_gt          0.1326
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.973
_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 -0.17864(11) 0.42447(9) -0.02137(5) 0.02024(15) Uani 1 1 d . . .
C2 C -0.07604(13) 0.50484(12) 0.08790(6) 0.02698(19) Uani 1 1 d . . .
H2A H -0.1014 0.4534 0.1335 0.032 Uiso 1 1 calc R . .
H2B H -0.0472 0.6004 0.1011 0.032 Uiso 1 1 calc R . .
C3 C 0.06568(12) 0.43658(9) 0.04591(5) 0.02041(15) Uani 1 1 d . . .
H3 H 0.1171 0.3625 0.0763 0.024 Uiso 1 1 calc R . .
C4 C 0.19688(11) 0.53563(9) 0.01810(5) 0.01937(15) Uani 1 1 d . . .
H4 H 0.1423 0.6148 -0.0071 0.023 Uiso 1 1 calc R . .
C5 C 0.30936(11) 0.46186(9) -0.03621(6) 0.02140(16) Uani 1 1 d . . .
H5 H 0.3657 0.3841 -0.0106 0.026 Uiso 1 1 calc R . .
C6 C 0.20792(12) 0.40522(10) -0.10073(5) 0.02152(16) Uani 1 1 d . . .
H6 H 0.1633 0.4832 -0.1305 0.026 Uiso 1 1 calc R . .
C7 C 0.06599(12) 0.31301(10) -0.07621(5) 0.02175(16) Uani 1 1 d . . .
H7A H -0.0100 0.2969 -0.1180 0.026 Uiso 1 1 calc R . .
H7B H 0.1098 0.2232 -0.0599 0.026 Uiso 1 1 calc R . .
C8 C 0.3138(2) 0.72867(12) 0.07739(8) 0.0398(3) Uani 1 1 d . . .
H8A H 0.2073 0.7785 0.0778 0.048 Uiso 1 1 calc R . .
H8B H 0.3722 0.7516 0.0312 0.048 Uiso 1 1 calc R . .
C9 C 0.41649(15) 0.77198(10) 0.14231(6) 0.02585(19) Uani 1 1 d . . .
C10 C 0.35035(19) 0.86053(15) 0.19398(9) 0.0421(3) Uani 1 1 d . . .
H10 H 0.2395 0.8911 0.1894 0.050 Uiso 1 1 calc R . .
C11 C 0.4469(3) 0.90471(16) 0.25282(9) 0.0586(6) Uani 1 1 d . . .
H11 H 0.4014 0.9652 0.2884 0.070 Uiso 1 1 calc R . .
C12 C 0.6085(3) 0.86107(16) 0.25974(8) 0.0521(5) Uani 1 1 d . . .
H12 H 0.6743 0.8917 0.2998 0.063 Uiso 1 1 calc R . .
C13 C 0.6732(2) 0.77296(16) 0.20823(9) 0.0462(4) Uani 1 1 d . . .
H13 H 0.7838 0.7417 0.2130 0.055 Uiso 1 1 calc R . .
C14 C 0.57798(17) 0.72954(12) 0.14951(7) 0.0316(2) Uani 1 1 d . . .
H14 H 0.6244 0.6698 0.1138 0.038 Uiso 1 1 calc R . .
N1 N -0.02250(10) 0.37780(9) -0.01632(5) 0.02047(14) Uani 1 1 d . . .
N2 N 0.31563(13) 0.31885(11) -0.14764(6) 0.0319(2) Uani 1 1 d . . .
N3 N 0.38938(15) 0.38163(14) -0.19657(6) 0.0385(3) Uani 1 1 d . . .
N4 N 0.4639(2) 0.4260(2) -0.24346(9) 0.0637(5) Uani 1 1 d . . .
O1 O -0.27950(9) 0.40179(9) -0.06950(5) 0.02706(15) Uani 1 1 d . . .
O2 O -0.21546(10) 0.50220(9) 0.03810(4) 0.02574(15) Uani 1 1 d . . .
O3 O 0.28435(10) 0.58387(7) 0.08077(4) 0.02349(14) Uani 1 1 d . . .
O4 O 0.42991(10) 0.55370(9) -0.06358(6) 0.03030(17) Uani 1 1 d . . .
H4A H 0.5226 0.5151 -0.0636 0.045 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
C1 O1 1.2173(12) . ?
C1 N1 1.3472(12) . ?
C1 O2 1.3534(12) . ?
C2 O2 1.4478(14) . ?
C2 C3 1.5308(15) . ?
C3 N1 1.4555(12) . ?
C3 C4 1.5221(13) . ?
C4 O3 1.4217(12) . ?
C4 C5 1.5239(14) . ?
C5 O4 1.4150(12) . ?
C5 C6 1.5349(14) . ?
C6 N2 1.4823(14) . ?
C6 C7 1.5258(14) . ?
C7 N1 1.4485(13) . ?
C8 O3 1.4324(14) . ?
C8 C9 1.5045(17) . ?
C9 C14 1.3783(17) . ?
C9 C10 1.3835(17) . ?
C10 C11 1.394(3) . ?
C11 C12 1.382(3) . ?
C12 C13 1.374(3) . ?
C13 C14 1.3832(19) . ?
N2 N3 1.2339(16) . ?
N3 N4 1.1307(18) . ?

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
O1 C1 N1 128.16(9) . . ?
O1 C1 O2 121.86(9) . . ?
N1 C1 O2 109.96(8) . . ?
O2 C2 C3 105.39(8) . . ?
N1 C3 C4 109.52(8) . . ?
N1 C3 C2 100.99(8) . . ?
C4 C3 C2 114.44(8) . . ?
O3 C4 C3 106.95(7) . . ?
O3 C4 C5 112.16(8) . . ?
C3 C4 C5 109.49(7) . . ?
O4 C5 C4 110.01(8) . . ?
O4 C5 C6 109.16(8) . . ?
C4 C5 C6 110.16(7) . . ?
N2 C6 C7 106.09(9) . . ?
N2 C6 C5 109.19(8) . . ?
C7 C6 C5 113.08(8) . . ?
N1 C7 C6 109.62(8) . . ?
O3 C8 C9 109.55(9) . . ?
C14 C9 C10 119.35(12) . . ?
C14 C9 C8 121.02(12) . . ?
C10 C9 C8 119.57(12) . . ?
C9 C10 C11 119.77(14) . . ?
C12 C11 C10 120.44(13) . . ?
C13 C12 C11 119.43(14) . . ?
C12 C13 C14 120.28(16) . . ?
C9 C14 C13 120.72(13) . . ?
C1 N1 C7 124.10(8) . . ?
C1 N1 C3 112.39(8) . . ?
C7 N1 C3 120.86(8) . . ?
N3 N2 C6 114.72(11) . . ?
N4 N3 N2 172.65(16) . . ?
C1 O2 C2 109.74(8) . . ?
C4 O3 C8 111.98(8) . . ?

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
O2 C2 C3 N1 -11.76(10) . . . . ?
O2 C2 C3 C4 105.77(9) . . . . ?
N1 C3 C4 O3 -176.93(7) . . . . ?
C2 C3 C4 O3 70.53(10) . . . . ?
N1 C3 C4 C5 -55.18(9) . . . . ?
C2 C3 C4 C5 -167.72(8) . . . . ?
O3 C4 C5 O4 -62.60(10) . . . . ?
C3 C4 C5 O4 178.84(8) . . . . ?
O3 C4 C5 C6 177.01(7) . . . . ?
C3 C4 C5 C6 58.45(9) . . . . ?
O4 C5 C6 N2 66.39(10) . . . . ?
C4 C5 C6 N2 -172.71(8) . . . . ?
O4 C5 C6 C7 -175.75(8) . . . . ?
C4 C5 C6 C7 -54.85(10) . . . . ?
N2 C6 C7 N1 166.04(8) . . . . ?
C5 C6 C7 N1 46.38(10) . . . . ?
O3 C8 C9 C14 67.10(16) . . . . ?
O3 C8 C9 C10 -115.73(13) . . . . ?
C14 C9 C10 C11 -0.54(19) . . . . ?
C8 C9 C10 C11 -177.77(12) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C10 C11 C12 C13 -0.3(2) . . . . ?
C11 C12 C13 C14 0.7(2) . . . . ?
C10 C9 C14 C13 0.93(18) . . . . ?
C8 C9 C14 C13 178.12(11) . . . . ?
C12 C13 C14 C9 -1.0(2) . . . . ?
O1 C1 N1 C7 13.36(16) . . . . ?
O2 C1 N1 C7 -168.30(9) . . . . ?
O1 C1 N1 C3 174.94(9) . . . . ?
O2 C1 N1 C3 -6.71(11) . . . . ?
C6 C7 N1 C1 112.65(10) . . . . ?
C6 C7 N1 C3 -47.46(11) . . . . ?
C4 C3 N1 C1 -109.55(9) . . . . ?
C2 C3 N1 C1 11.52(10) . . . . ?
C4 C3 N1 C7 52.71(11) . . . . ?
C2 C3 N1 C7 173.78(9) . . . . ?
C7 C6 N2 N3 149.45(11) . . . . ?
C5 C6 N2 N3 -88.39(12) . . . . ?
C6 N2 N3 N4 -180(100) . . . . ?
O1 C1 O2 C2 176.63(9) . . . . ?
N1 C1 O2 C2 -1.83(11) . . . . ?
C3 C2 O2 C1 8.93(11) . . . . ?
C3 C4 O3 C8 -136.74(10) . . . . ?
C5 C4 O3 C8 103.21(11) . . . . ?
C9 C8 O3 C4 -176.12(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        36.57
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.074
####################################################################### 
# 
# 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_AFC561_0m
_database_code_depnum_ccdc_archive 'CCDC 1053545'
_audit_update_record             
;
2015-03-12 deposited with the CCDC.
2015-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 N4 O4'
_chemical_formula_weight         304.31
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_space_group_IT_number           19
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   9.6858(9)
_cell_length_b                   9.9838(6)
_cell_length_c                   15.1087(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1461.03(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1547
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      30.88

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.997
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            9047
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.445
_diffrn_reflns_theta_max         31.581
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4568
_reflns_number_gt                4142
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_max     0.898
_reflns_Friedel_fraction_full    0.992

_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       'Bruker APEX2 v2011.4-0'
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0835P)²+0.0375P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1604 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_chemical_absolute_configuration ad
_refine_ls_abs_structure_Flack   0.6(8)
_refine_ls_number_reflns         4568
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1614
_refine_ls_wR_factor_gt          0.1555
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9114(3) 1.0986(2) 0.11576(15) 0.0216(4) Uani 1 1 d . . . . .
C2 C 0.7035(3) 0.9969(2) 0.08700(17) 0.0232(5) Uani 1 1 d . . . . .
H2A H 0.6591 1.0184 0.0297 0.028 Uiso 1 1 calc R U . . .
H2B H 0.6322 0.9633 0.1284 0.028 Uiso 1 1 calc R U . . .
C3 C 0.8186(2) 0.8928(2) 0.07451(14) 0.0176(4) Uani 1 1 d . . . . .
H3 H 0.8128 0.8516 0.0143 0.021 Uiso 1 1 calc R U . . .
C4 C 0.8219(2) 0.78372(18) 0.14594(14) 0.0161(4) Uani 1 1 d . . . . .
H4 H 0.8043 0.8255 0.2050 0.019 Uiso 1 1 calc R U . . .
C5 C 0.9626(2) 0.7129(2) 0.14760(15) 0.0190(4) Uani 1 1 d . . . . .
H5 H 0.9643 0.6447 0.1961 0.023 Uiso 1 1 calc R U . . .
C6 C 1.0804(2) 0.8153(2) 0.16146(17) 0.0226(4) Uani 1 1 d . . . . .
H6 H 1.1712 0.7676 0.1615 0.027 Uiso 1 1 calc R U . . .
C7 C 1.0790(3) 0.9193(2) 0.08727(18) 0.0235(4) Uani 1 1 d . . . . .
H7A H 1.1477 0.9903 0.0997 0.028 Uiso 1 1 calc R U . . .
H7B H 1.1035 0.8763 0.0304 0.028 Uiso 1 1 calc R U . . .
C8 C 0.6680(3) 0.6153(2) 0.20040(15) 0.0236(5) Uani 1 1 d . . . . .
H81 H 0.6379 0.6745 0.2493 0.028 Uiso 1 1 calc R U . . .
H82 H 0.7458 0.5597 0.2218 0.028 Uiso 1 1 calc R U . . .
C9 C 0.5503(3) 0.5271(2) 0.17144(15) 0.0203(4) Uani 1 1 d . . . . .
C10 C 0.4130(3) 0.5679(2) 0.18180(17) 0.0248(5) Uani 1 1 d . . . . .
H10 H 0.3934 0.6524 0.2079 0.030 Uiso 1 1 calc R U . . .
C11 C 0.3048(3) 0.4862(2) 0.15422(19) 0.0286(5) Uani 1 1 d . . . . .
H11 H 0.2121 0.5148 0.1619 0.034 Uiso 1 1 calc R U . . .
C12 C 0.3324(3) 0.3628(2) 0.11538(17) 0.0285(5) Uani 1 1 d . . . . .
H12 H 0.2589 0.3070 0.0962 0.034 Uiso 1 1 calc R U . . .
C13 C 0.4686(3) 0.3219(2) 0.10496(18) 0.0306(6) Uani 1 1 d . . . . .
H13 H 0.4878 0.2381 0.0779 0.037 Uiso 1 1 calc R U . . .
C14 C 0.5772(3) 0.4023(2) 0.13375(18) 0.0256(5) Uani 1 1 d . . . . .
H14 H 0.6697 0.3721 0.1277 0.031 Uiso 1 1 calc R U . . .
N1 N 0.9415(2) 0.97754(17) 0.08149(13) 0.0189(4) Uani 1 1 d . . . . .
N2 N 0.9924(2) 0.64676(19) 0.06065(15) 0.0261(4) Uani 1 1 d . . . . .
N3 N 0.9236(2) 0.54636(19) 0.04299(15) 0.0261(4) Uani 1 1 d . . . . .
N4 N 0.8718(3) 0.4522(2) 0.0169(2) 0.0397(6) Uani 1 1 d . . . . .
O1 O 0.9928(2) 1.18644(16) 0.13734(12) 0.0278(4) Uani 1 1 d . . . . .
O2 O 0.7726(2) 1.11432(15) 0.12339(13) 0.0268(4) Uani 1 1 d . . . . .
O3 O 1.0628(2) 0.88378(15) 0.24352(12) 0.0264(4) Uani 1 1 d . . . . .
H3A H 1.0554 0.8225 0.2828 0.040 Uiso 1 1 d R U . . .
O4 O 0.71125(18) 0.69488(14) 0.12515(10) 0.0179(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 O1 1.224(3) . ?
C1 N1 1.346(3) . ?
C1 O2 1.359(3) . ?
C2 O2 1.457(3) . ?
C2 C3 1.537(3) . ?
C3 N1 1.464(3) . ?
C3 C4 1.534(3) . ?
C4 O4 1.426(2) . ?
C4 C5 1.536(3) . ?
C5 N2 1.498(3) . ?
C5 C6 1.547(3) . ?
C6 O3 1.426(3) . ?
C6 C7 1.528(3) . ?
C7 N1 1.456(3) . ?
C8 O4 1.449(3) . ?
C8 C9 1.506(3) . ?
C9 C14 1.395(3) . ?
C9 C10 1.400(3) . ?
C10 C11 1.391(4) . ?
C11 C12 1.391(4) . ?
C12 C13 1.389(4) . ?
C13 C14 1.393(4) . ?
N2 N3 1.233(3) . ?
N3 N4 1.137(3) . ?

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
O1 C1 N1 127.4(2) . . ?
O1 C1 O2 122.1(2) . . ?
N1 C1 O2 110.5(2) . . ?
O2 C2 C3 104.89(18) . . ?
N1 C3 C4 110.07(16) . . ?
N1 C3 C2 100.96(16) . . ?
C4 C3 C2 114.13(18) . . ?
O4 C4 C3 105.73(16) . . ?
O4 C4 C5 112.58(15) . . ?
C3 C4 C5 110.90(17) . . ?
N2 C5 C4 111.05(18) . . ?
N2 C5 C6 105.56(19) . . ?
C4 C5 C6 110.62(16) . . ?
O3 C6 C7 108.14(17) . . ?
O3 C6 C5 110.26(19) . . ?
C7 C6 C5 110.08(19) . . ?
N1 C7 C6 108.87(19) . . ?
O4 C8 C9 108.15(18) . . ?
C14 C9 C10 118.9(2) . . ?
C14 C9 C8 120.0(2) . . ?
C10 C9 C8 121.1(2) . . ?
C11 C10 C9 120.7(2) . . ?
C12 C11 C10 120.1(2) . . ?
C13 C12 C11 119.4(2) . . ?
C12 C13 C14 120.8(2) . . ?
C13 C14 C9 120.1(3) . . ?
C1 N1 C7 122.2(2) . . ?
C1 N1 C3 111.78(19) . . ?
C7 N1 C3 121.13(16) . . ?
N3 N2 C5 116.4(2) . . ?
N4 N3 N2 170.6(3) . . ?
C1 O2 C2 109.24(17) . . ?
C4 O4 C8 112.66(16) . . ?

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
O2 C2 C3 N1 -15.5(2) . . . . ?
O2 C2 C3 C4 102.5(2) . . . . ?
N1 C3 C4 O4 -171.07(16) . . . . ?
C2 C3 C4 O4 76.3(2) . . . . ?
N1 C3 C4 C5 -48.8(2) . . . . ?
C2 C3 C4 C5 -161.42(18) . . . . ?
O4 C4 C5 N2 57.7(2) . . . . ?
C3 C4 C5 N2 -60.6(2) . . . . ?
O4 C4 C5 C6 174.56(18) . . . . ?
C3 C4 C5 C6 56.3(2) . . . . ?
N2 C5 C6 O3 -179.47(17) . . . . ?
C4 C5 C6 O3 60.3(2) . . . . ?
N2 C5 C6 C7 61.3(2) . . . . ?
C4 C5 C6 C7 -58.9(2) . . . . ?
O3 C6 C7 N1 -67.1(2) . . . . ?
C5 C6 C7 N1 53.4(2) . . . . ?
O4 C8 C9 C14 87.2(3) . . . . ?
O4 C8 C9 C10 -92.9(3) . . . . ?
C14 C9 C10 C11 -0.6(3) . . . . ?
C8 C9 C10 C11 179.5(2) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C11 C12 C13 C14 0.7(4) . . . . ?
C12 C13 C14 C9 -1.7(4) . . . . ?
C10 C9 C14 C13 1.7(4) . . . . ?
C8 C9 C14 C13 -178.5(2) . . . . ?
O1 C1 N1 C7 17.2(4) . . . . ?
O2 C1 N1 C7 -163.5(2) . . . . ?
O1 C1 N1 C3 172.7(2) . . . . ?
O2 C1 N1 C3 -8.0(3) . . . . ?
C6 C7 N1 C1 101.3(2) . . . . ?
C6 C7 N1 C3 -51.9(3) . . . . ?
C4 C3 N1 C1 -106.2(2) . . . . ?
C2 C3 N1 C1 14.7(2) . . . . ?
C4 C3 N1 C7 49.5(3) . . . . ?
C2 C3 N1 C7 170.5(2) . . . . ?
C4 C5 N2 N3 -71.3(3) . . . . ?
C6 C5 N2 N3 168.8(2) . . . . ?
O1 C1 O2 C2 176.2(2) . . . . ?
N1 C1 O2 C2 -3.2(3) . . . . ?
C3 C2 O2 C1 12.2(3) . . . . ?
C3 C4 O4 C8 -159.37(17) . . . . ?
C5 C4 O4 C8 79.4(2) . . . . ?
C9 C8 O4 C4 179.24(18) . . . . ?

_refine_diff_density_max         0.423
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.073
_shelxl_version_number           2014-3
