# 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 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_20151231b_0m
_database_code_depnum_ccdc_archive 'CCDC 1504801'
_audit_update_record             
;
2016-09-20 deposited with the CCDC.
2017-02-28 downloaded from the CCDC.
;
_audit_creation_date             2016-09-02
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 N2 O4'
_chemical_formula_sum            'C18 H16 N2 O4'
_chemical_formula_weight         324.33
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.220(11)
_cell_length_b                   7.030(3)
_cell_length_c                   8.168(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.038(8)
_cell_angle_gamma                90
_cell_volume                     1614.2(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    647
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.468
_cell_measurement_theta_min      2.898
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0684 before and 0.0423 after correction.
The Ratio of minimum to maximum transmission is 0.8546.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         2.898
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                806
_reflns_number_total             1964
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1964
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1497
_refine_ls_R_factor_gt           0.0576
_refine_ls_restrained_S_all      0.980
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0879P)²+0.0583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1525
_refine_ls_wR_factor_ref         0.1969
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: N1(0.5) N2(0.5) H3(0.5) H5(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
3.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.65808(5) 0.7718(2) 0.1914(2) 0.0709(6) Uani 1 1 d . . . . .
O2 O 0.67805(7) 0.4659(3) 0.2136(3) 0.1018(8) Uani 1 1 d . . . . .
N1 N 0.51272(15) 0.8232(6) 0.4801(6) 0.0703(12) Uani 0.5 1 d . . P A 1
N2 N 0.47274(15) 0.7969(5) 0.5500(5) 0.0712(12) Uani 0.5 1 d . . P A 1
C1 C 0.60591(8) 0.5699(4) 0.3128(3) 0.0633(7) Uani 1 1 d . . . . .
C2 C 0.57923(9) 0.7249(4) 0.3571(3) 0.0708(8) Uani 1 1 d . . . . .
H2 H 0.5893 0.8477 0.3362 0.085 Uiso 1 1 calc R . . . .
C3 C 0.53802(9) 0.6974(5) 0.4316(3) 0.0835(9) Uani 1 1 d . . . . .
H3 H 0.5209 0.8025 0.4623 0.100 Uiso 0.5 1 calc R . P A 2
C4 C 0.52125(10) 0.5150(6) 0.4622(3) 0.0920(10) Uani 1 1 d . . . . .
C5 C 0.54798(12) 0.3630(6) 0.4141(4) 0.0942(10) Uani 1 1 d . . . . .
H5 H 0.5374 0.2400 0.4315 0.113 Uiso 0.5 1 calc R . P B 2
C6 C 0.58967(10) 0.3877(4) 0.3415(3) 0.0765(8) Uani 1 1 d . . . . .
H6 H 0.6070 0.2825 0.3116 0.092 Uiso 1 1 calc R . . . .
C7 C 0.65095(10) 0.5930(4) 0.2356(3) 0.0690(7) Uani 1 1 d . . . . .
C8 C 0.70122(9) 0.8103(4) 0.1138(4) 0.0795(9) Uani 1 1 d . . . . .
H8A H 0.7026 0.7301 0.0177 0.095 Uiso 1 1 calc R . . . .
H8B H 0.7288 0.7831 0.1897 0.095 Uiso 1 1 calc R . . . .
C9 C 0.70118(11) 1.0116(4) 0.0657(4) 0.0960(10) Uani 1 1 d . . . . .
H9A H 0.6739 1.0370 -0.0099 0.144 Uiso 1 1 calc GR . . . .
H9B H 0.7297 1.0395 0.0141 0.144 Uiso 1 1 calc GR . . . .
H9C H 0.6999 1.0899 0.1616 0.144 Uiso 1 1 calc GR . . . .


_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 C7 1.328(3) . ?
O1 C8 1.446(3) . ?
O2 C7 1.200(3) . ?
N1 N2 1.322(6) . ?
N1 C3 1.224(5) . ?
N2 C5 1.312(5) 5_666 ?
C1 C2 1.390(3) . ?
C1 C6 1.388(4) . ?
C1 C7 1.476(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.373(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.397(4) . ?
C4 C4 1.413(6) 5_666 ?
C4 C5 1.385(5) . ?
C5 N2 1.312(5) 5_666 ?
C5 H5 0.9300 . ?
C5 C6 1.374(4) . ?
C6 H6 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.469(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C8 116.7(2) . . ?
C3 N1 N2 125.7(4) . . ?
C5 N2 N1 129.1(4) 5_666 . ?
C2 C1 C7 122.1(2) . . ?
C6 C1 C2 119.0(2) . . ?
C6 C1 C7 118.9(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.9 . . ?
N1 C3 C2 125.6(4) . . ?
N1 C3 C4 112.9(3) . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.5(3) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C4 122.0(5) . 5_666 ?
C5 C4 C3 117.1(3) . . ?
C5 C4 C4 120.9(5) . 5_666 ?
N2 C5 C4 109.5(4) 5_666 . ?
N2 C5 C6 128.3(4) 5_666 . ?
C4 C5 H5 118.9 . . ?
C6 C5 C4 122.2(3) . . ?
C6 C5 H5 118.9 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
O1 C7 C1 112.1(2) . . ?
O2 C7 O1 123.4(3) . . ?
O2 C7 C1 124.5(3) . . ?
O1 C8 H8A 110.0 . . ?
O1 C8 H8B 110.0 . . ?
O1 C8 C9 108.4(2) . . ?
H8A C8 H8B 108.4 . . ?
C9 C8 H8A 110.0 . . ?
C9 C8 H8B 110.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
N1 C3 C4 C4 1.5(5) . . . 5_666 ?
N1 C3 C4 C5 -179.0(3) . . . . ?
N2 N1 C3 C2 179.1(4) . . . . ?
N2 N1 C3 C4 -2.0(6) . . . . ?
N2 C5 C6 C1 179.8(3) 5_666 . . . ?
C1 C2 C3 N1 177.6(3) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
C2 C1 C7 O1 -10.1(4) . . . . ?
C2 C1 C7 O2 170.5(3) . . . . ?
C2 C3 C4 C4 -179.6(3) . . . 5_666 ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 N1 N2 C5 1.6(8) . . . 5_666 ?
C3 C4 C5 N2 -179.4(3) . . . 5_666 ?
C3 C4 C5 C6 1.0(4) . . . . ?
C4 C4 C5 N2 0.1(5) 5_666 . . 5_666 ?
C4 C4 C5 C6 -179.5(3) 5_666 . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C6 C1 C2 C3 1.5(4) . . . . ?
C6 C1 C7 O1 169.7(2) . . . . ?
C6 C1 C7 O2 -9.8(4) . . . . ?
C7 O1 C8 C9 176.7(2) . . . . ?
C7 C1 C2 C3 -178.7(2) . . . . ?
C7 C1 C6 C5 179.6(2) . . . . ?
C8 O1 C7 O2 -0.3(4) . . . . ?
C8 O1 C7 C1 -179.8(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_20151229l_0m
_database_code_depnum_ccdc_archive 'CCDC 1504861'
_audit_update_record             
;
2016-10-09 deposited with the CCDC.
2017-02-28 downloaded from the CCDC.
;
_audit_creation_date             2016-10-08
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 N2 O5'
_chemical_formula_sum            'C18 H16 N2 O5'
_chemical_formula_weight         340.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   8.2607(15)
_cell_length_b                   14.168(3)
_cell_length_c                   27.700(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3241.9(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2761
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.485
_cell_measurement_theta_min      2.854
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1004 before and 0.0471 after correction.
The Ratio of minimum to maximum transmission is 0.8473.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            19537
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.251
_diffrn_reflns_theta_min         1.470
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2039
_reflns_number_total             3964
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0020(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3964
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1385
_refine_ls_R_factor_gt           0.0651
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0683P)²+1.8323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.1885
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(O5A)=1-FVAR(1)
 Sof(O5)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C19(H19A,H19B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C12(H12), C13(H13), C16(H16), C0AA(H0AA), C17(H17)
3.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O4 O 0.6490(4) 0.37408(16) 0.43464(8) 0.0966(9) Uani 1 1 d . . . . .
O2AA O -0.1057(3) 0.32431(19) 0.08892(9) 0.0909(8) Uani 1 1 d . . . . .
O0AA O 0.6716(3) 0.22107(13) 0.41854(7) 0.0636(6) Uani 1 1 d . . . . .
O1AA O -0.0912(3) 0.47632(17) 0.10679(8) 0.0856(8) Uani 1 1 d . . . . .
C14 C 0.3247(3) 0.32289(17) 0.28283(9) 0.0425(6) Uani 1 1 d . . . . .
C15 C 0.2268(3) 0.33468(17) 0.24038(9) 0.0431(6) Uani 1 1 d . . . . .
C6 C 0.3815(3) 0.40325(16) 0.30631(9) 0.0429(6) Uani 1 1 d . . . . .
C8 C 0.5170(3) 0.31146(17) 0.36587(9) 0.0460(6) Uani 1 1 d . . . . .
C7 C 0.4771(3) 0.39801(17) 0.34750(9) 0.0468(6) Uani 1 1 d . . . . .
H7 H 0.5137 0.4528 0.3624 0.056 Uiso 1 1 calc R . . . .
C4 C 0.1967(3) 0.42784(18) 0.22566(9) 0.0480(7) Uani 1 1 d . . . . .
C12 C 0.4622(3) 0.23021(18) 0.34277(9) 0.0506(7) Uani 1 1 d . . . . .
H12 H 0.4905 0.1714 0.3550 0.061 Uiso 1 1 calc R . . . .
C13 C 0.3673(3) 0.23537(18) 0.30234(10) 0.0501(7) Uani 1 1 d . . . . .
H13 H 0.3309 0.1802 0.2877 0.060 Uiso 1 1 calc R . . . .
C16 C 0.1606(3) 0.26132(19) 0.21354(10) 0.0523(7) Uani 1 1 d . . . . .
H16 H 0.1786 0.1993 0.2230 0.063 Uiso 1 1 calc R . . . .
C0AA C 0.1036(3) 0.4457(2) 0.18454(10) 0.0545(7) Uani 1 1 d . . . . .
H0AA H 0.0845 0.5075 0.1748 0.065 Uiso 1 1 calc R . . . .
C17 C 0.0695(3) 0.2790(2) 0.17344(10) 0.0565(7) Uani 1 1 d . . . . .
H17 H 0.0263 0.2291 0.1559 0.068 Uiso 1 1 calc R . . . .
C2AA C 0.0406(3) 0.3720(2) 0.15861(9) 0.0543(7) Uani 1 1 d . . . . .
C9 C 0.6184(4) 0.3074(2) 0.41005(10) 0.0549(7) Uani 1 1 d . . . . .
C1AA C -0.0586(4) 0.3866(3) 0.11459(12) 0.0667(9) Uani 1 1 d . . . . .
C10 C 0.7748(4) 0.2064(2) 0.46033(11) 0.0739(10) Uani 1 1 d . . . . .
H10A H 0.7107 0.2065 0.4897 0.089 Uiso 1 1 calc R . . . .
H10B H 0.8550 0.2561 0.4626 0.089 Uiso 1 1 calc R . . . .
C11 C 0.8546(5) 0.1139(3) 0.45380(14) 0.0983(13) Uani 1 1 d . . . . .
H11A H 0.9207 0.1155 0.4253 0.147 Uiso 1 1 calc GR . . . .
H11B H 0.7738 0.0656 0.4505 0.147 Uiso 1 1 calc GR . . . .
H11C H 0.9211 0.1005 0.4814 0.147 Uiso 1 1 calc GR . . . .
C19 C -0.1877(6) 0.4952(3) 0.06351(15) 0.1131(16) Uani 1 1 d . . . . .
H19A H -0.1441 0.4598 0.0365 0.136 Uiso 1 1 calc R . . . .
H19B H -0.2984 0.4747 0.0688 0.136 Uiso 1 1 calc R . . . .
C20 C -0.1858(8) 0.5889(4) 0.05303(19) 0.160(3) Uani 1 1 d . . . . .
H20A H -0.2436 0.5998 0.0235 0.240 Uiso 1 1 calc GR . . . .
H20B H -0.0759 0.6097 0.0495 0.240 Uiso 1 1 calc GR . . . .
H20C H -0.2367 0.6234 0.0787 0.240 Uiso 1 1 calc GR . . . .
N1 N 0.3437(3) 0.49420(14) 0.28799(8) 0.0519(6) Uani 1 1 d . . . . .
O5 O 0.4004(3) 0.56612(14) 0.30969(9) 0.0680(10) Uani 0.840(5) 1 d . . P A 1
N3 N 0.2546(3) 0.50621(16) 0.24981(9) 0.0558(6) Uani 1 1 d . . . . .
O5A O 0.198(2) 0.5713(9) 0.2332(6) 0.108(7) Uani 0.160(5) 1 d . . P A 2


_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
O4 C9 1.191(3) . ?
O2AA C1AA 1.198(4) . ?
O0AA C9 1.321(3) . ?
O0AA C10 1.452(3) . ?
O1AA C1AA 1.318(4) . ?
O1AA C19 1.464(4) . ?
C14 C15 1.437(3) . ?
C14 C6 1.393(3) . ?
C14 C13 1.398(3) . ?
C15 C4 1.404(3) . ?
C15 C16 1.390(4) . ?
C6 C7 1.390(4) . ?
C6 N1 1.420(3) . ?
C8 C7 1.368(3) . ?
C8 C12 1.393(3) . ?
C8 C9 1.484(4) . ?
C7 H7 0.9300 . ?
C4 C0AA 1.397(4) . ?
C4 N3 1.382(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.369(4) . ?
C13 H13 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.365(4) . ?
C0AA H0AA 0.9300 . ?
C0AA C2AA 1.370(4) . ?
C17 H17 0.9300 . ?
C17 C2AA 1.400(4) . ?
C2AA C1AA 1.483(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.478(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.360(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N1 O5 1.272(3) . ?
N1 N3 1.300(3) . ?
N3 O5A 1.130(15) . ?

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
C9 O0AA C10 118.0(2) . . ?
C1AA O1AA C19 114.9(3) . . ?
C6 C14 C15 118.5(2) . . ?
C6 C14 C13 117.4(2) . . ?
C13 C14 C15 124.1(2) . . ?
C4 C15 C14 116.5(2) . . ?
C16 C15 C14 124.9(2) . . ?
C16 C15 C4 118.6(2) . . ?
C14 C6 N1 120.1(2) . . ?
C7 C6 C14 122.1(2) . . ?
C7 C6 N1 117.8(2) . . ?
C7 C8 C12 119.5(2) . . ?
C7 C8 C9 118.5(2) . . ?
C12 C8 C9 122.0(2) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.3(2) . . ?
C8 C7 H7 120.3 . . ?
C0AA C4 C15 120.3(2) . . ?
N3 C4 C15 123.6(2) . . ?
N3 C4 C0AA 116.1(2) . . ?
C8 C12 H12 119.4 . . ?
C13 C12 C8 121.2(2) . . ?
C13 C12 H12 119.4 . . ?
C14 C13 H13 119.7 . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13 119.7 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.0(3) . . ?
C17 C16 H16 119.5 . . ?
C4 C0AA H0AA 120.1 . . ?
C2AA C0AA C4 119.9(3) . . ?
C2AA C0AA H0AA 120.1 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C2AA 120.4(3) . . ?
C2AA C17 H17 119.8 . . ?
C0AA C2AA C17 119.9(3) . . ?
C0AA C2AA C1AA 122.3(3) . . ?
C17 C2AA C1AA 117.8(3) . . ?
O4 C9 O0AA 124.2(3) . . ?
O4 C9 C8 124.1(3) . . ?
O0AA C9 C8 111.7(2) . . ?
O2AA C1AA O1AA 123.1(3) . . ?
O2AA C1AA C2AA 124.4(3) . . ?
O1AA C1AA C2AA 112.5(3) . . ?
O0AA C10 H10A 110.3 . . ?
O0AA C10 H10B 110.3 . . ?
O0AA C10 C11 106.9(3) . . ?
H10A C10 H10B 108.6 . . ?
C11 C10 H10A 110.3 . . ?
C11 C10 H10B 110.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1AA C19 H19A 109.6 . . ?
O1AA C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
C20 C19 O1AA 110.3(4) . . ?
C20 C19 H19A 109.6 . . ?
C20 C19 H19B 109.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 N1 C6 118.5(2) . . ?
O5 N1 N3 119.2(2) . . ?
N3 N1 C6 122.3(2) . . ?
N1 N3 C4 119.0(2) . . ?
O5A N3 C4 108.5(8) . . ?
O5A N3 N1 132.1(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
C14 C15 C4 C0AA 179.5(2) . . . . ?
C14 C15 C4 N3 -0.4(4) . . . . ?
C14 C15 C16 C17 -179.7(2) . . . . ?
C14 C6 C7 C8 -0.1(4) . . . . ?
C14 C6 N1 O5 -178.5(2) . . . . ?
C14 C6 N1 N3 1.0(4) . . . . ?
C15 C14 C6 C7 -179.8(2) . . . . ?
C15 C14 C6 N1 -0.6(3) . . . . ?
C15 C14 C13 C12 179.5(2) . . . . ?
C15 C4 C0AA C2AA 0.4(4) . . . . ?
C15 C4 N3 N1 0.8(4) . . . . ?
C15 C4 N3 O5A -172.4(11) . . . . ?
C15 C16 C17 C2AA -0.2(4) . . . . ?
C6 C14 C15 C4 0.3(3) . . . . ?
C6 C14 C15 C16 -179.4(2) . . . . ?
C6 C14 C13 C12 -0.4(4) . . . . ?
C6 N1 N3 C4 -1.1(4) . . . . ?
C6 N1 N3 O5A 170.3(14) . . . . ?
C8 C12 C13 C14 0.8(4) . . . . ?
C7 C6 N1 O5 0.8(4) . . . . ?
C7 C6 N1 N3 -179.7(2) . . . . ?
C7 C8 C12 C13 -0.9(4) . . . . ?
C7 C8 C9 O4 11.1(5) . . . . ?
C7 C8 C9 O0AA -168.4(2) . . . . ?
C4 C15 C16 C17 0.6(4) . . . . ?
C4 C0AA C2AA C17 0.1(4) . . . . ?
C4 C0AA C2AA C1AA -179.8(3) . . . . ?
C12 C8 C7 C6 0.5(4) . . . . ?
C12 C8 C9 O4 -169.1(3) . . . . ?
C12 C8 C9 O0AA 11.4(4) . . . . ?
C13 C14 C15 C4 -179.6(2) . . . . ?
C13 C14 C15 C16 0.7(4) . . . . ?
C13 C14 C6 C7 0.1(4) . . . . ?
C13 C14 C6 N1 179.4(2) . . . . ?
C16 C15 C4 C0AA -0.8(4) . . . . ?
C16 C15 C4 N3 179.3(2) . . . . ?
C16 C17 C2AA C0AA -0.2(4) . . . . ?
C16 C17 C2AA C1AA 179.7(3) . . . . ?
C0AA C4 N3 N1 -179.1(2) . . . . ?
C0AA C4 N3 O5A 7.6(11) . . . . ?
C0AA C2AA C1AA O2AA 174.2(3) . . . . ?
C0AA C2AA C1AA O1AA -6.4(4) . . . . ?
C17 C2AA C1AA O2AA -5.7(5) . . . . ?
C17 C2AA C1AA O1AA 173.7(3) . . . . ?
C9 O0AA C10 C11 -163.8(3) . . . . ?
C9 C8 C7 C6 -179.7(2) . . . . ?
C9 C8 C12 C13 179.3(3) . . . . ?
C1AA O1AA C19 C20 -167.1(5) . . . . ?
C10 O0AA C9 O4 -0.4(5) . . . . ?
C10 O0AA C9 C8 179.1(2) . . . . ?
C19 O1AA C1AA O2AA -1.1(5) . . . . ?
C19 O1AA C1AA C2AA 179.5(3) . . . . ?
N1 C6 C7 C8 -179.4(2) . . . . ?
O5 N1 N3 C4 178.4(2) . . . . ?
N3 C4 C0AA C2AA -179.6(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
