# 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_cu_M35_R_0m
_database_code_depnum_ccdc_archive 'CCDC 1489354'
_audit_update_record             
;
2016-07-01 deposited with the CCDC.
2017-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 N O2'
_chemical_formula_sum            'C17 H15 N O2'
_chemical_formula_weight         265.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   5.6408(8)
_cell_length_b                   10.3136(10)
_cell_length_c                   12.233(2)
_cell_angle_alpha                74.130(5)
_cell_angle_beta                 89.422(6)
_cell_angle_gamma                86.861(6)
_cell_volume                     683.52(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5976
_cell_measurement_theta_min      3.76
_cell_measurement_theta_max      68.33

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.679
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9107
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.756
_diffrn_reflns_theta_max         68.323
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             2424
_reflns_number_gt                1936
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.1994P)²+0.1965P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    RIDING
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2424
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0806
_refine_ls_wR_factor_ref         0.2647
_refine_ls_wR_factor_gt          0.2400
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.3316(5) 0.55602(19) 0.36185(19) 0.0611(7) Uani 1 1 d . . . . .
O2 O -0.1800(3) 0.3673(2) 0.28060(19) 0.0544(6) Uani 1 1 d . . . . .
N5 N 0.4169(4) 0.3435(2) 0.47858(19) 0.0447(7) Uani 1 1 d . . . . .
H5 H 0.4669 0.3664 0.5364 0.054 Uiso 1 1 calc R U . . .
C1 C 0.3317(5) 0.4327(3) 0.3847(2) 0.0405(7) Uani 1 1 d . . . . .
C2 C 0.2387(4) 0.3535(2) 0.3064(2) 0.0311(6) Uani 1 1 d . . . . .
H2 H 0.3570 0.3524 0.2475 0.037 Uiso 1 1 calc R U . . .
C3 C 0.2250(4) 0.2102(2) 0.3844(2) 0.0334(6) Uani 1 1 d . . . . .
H3 H 0.0702 0.2034 0.4221 0.040 Uiso 1 1 calc R U . . .
C4 C 0.4177(5) 0.2054(2) 0.4743(2) 0.0398(7) Uani 1 1 d . . . . .
H4A H 0.3772 0.1459 0.5474 0.048 Uiso 1 1 calc R U . . .
H4B H 0.5713 0.1756 0.4510 0.048 Uiso 1 1 calc R U . . .
C1' C 0.2552(4) 0.0980(2) 0.3274(2) 0.0330(6) Uani 1 1 d . . . . .
C2' C 0.0889(5) -0.0002(3) 0.3439(2) 0.0410(7) Uani 1 1 d . . . . .
H2' H -0.0442 0.0058 0.3881 0.049 Uiso 1 1 calc R U . . .
C3' C 0.1179(6) -0.1062(3) 0.2957(3) 0.0544(8) Uani 1 1 d . . . . .
H3' H 0.0052 -0.1712 0.3082 0.065 Uiso 1 1 calc R U . . .
C4' C 0.3129(6) -0.1164(3) 0.2293(3) 0.0551(9) Uani 1 1 d . . . . .
H4' H 0.3329 -0.1880 0.1969 0.066 Uiso 1 1 calc R U . . .
C5' C 0.4787(6) -0.0188(3) 0.2113(3) 0.0525(8) Uani 1 1 d . . . . .
H5' H 0.6096 -0.0242 0.1656 0.063 Uiso 1 1 calc R U . . .
C6' C 0.4516(5) 0.0863(3) 0.2604(2) 0.0415(7) Uani 1 1 d . . . . .
H6' H 0.5661 0.1502 0.2487 0.050 Uiso 1 1 calc R U . . .
C7' C 0.0050(4) 0.4175(2) 0.2492(2) 0.0342(6) Uani 1 1 d . . . . .
C8' C 0.0132(4) 0.5439(2) 0.1556(2) 0.0351(6) Uani 1 1 d . . . . .
C9' C -0.1836(5) 0.6357(3) 0.1374(3) 0.0468(7) Uani 1 1 d . . . . .
H9' H -0.3132 0.6185 0.1858 0.056 Uiso 1 1 calc R U . . .
C10' C -0.1874(6) 0.7508(3) 0.0488(3) 0.0580(9) Uani 1 1 d . . . . .
H10' H -0.3185 0.8118 0.0383 0.070 Uiso 1 1 calc R U . . .
C11' C 0.0018(7) 0.7770(3) -0.0249(3) 0.0587(9) Uani 1 1 d . . . . .
H11' H -0.0029 0.8545 -0.0856 0.070 Uiso 1 1 calc R U . . .
C12' C 0.1979(6) 0.6878(3) -0.0082(3) 0.0572(9) Uani 1 1 d . . . . .
H12' H 0.3261 0.7051 -0.0575 0.069 Uiso 1 1 calc R U . . .
C13' C 0.2033(5) 0.5727(3) 0.0820(2) 0.0453(7) Uani 1 1 d . . . . .
H13' H 0.3370 0.5136 0.0936 0.054 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 C1 1.225(3) . ?
O2 C7' 1.203(3) . ?
N5 C1 1.335(3) . ?
N5 C4 1.439(3) . ?
N5 H5 0.8600 . ?
C1 C2 1.531(3) . ?
C2 C3 1.530(3) . ?
C2 C7' 1.528(3) . ?
C2 H2 0.9800 . ?
C3 C1' 1.507(3) . ?
C3 C4 1.543(3) . ?
C3 H3 0.9800 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C1' C2' 1.391(4) . ?
C1' C6' 1.391(4) . ?
C2' C3' 1.378(4) . ?
C2' H2' 0.9300 . ?
C3' C4' 1.378(5) . ?
C3' H3' 0.9300 . ?
C4' C5' 1.383(5) . ?
C4' H4' 0.9300 . ?
C5' C6' 1.377(4) . ?
C5' H5' 0.9300 . ?
C6' H6' 0.9300 . ?
C7' C8' 1.483(3) . ?
C8' C13' 1.385(4) . ?
C8' C9' 1.398(4) . ?
C9' C10' 1.370(4) . ?
C9' H9' 0.9300 . ?
C10' C11' 1.380(5) . ?
C10' H10' 0.9300 . ?
C11' C12' 1.379(5) . ?
C11' H11' 0.9300 . ?
C12' C13' 1.381(4) . ?
C12' H12' 0.9300 . ?
C13' H13' 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
C1 N5 C4 114.0(2) . . ?
C1 N5 H5 123.0 . . ?
C4 N5 H5 123.0 . . ?
O1 C1 N5 127.3(2) . . ?
O1 C1 C2 125.0(2) . . ?
N5 C1 C2 107.7(2) . . ?
C3 C2 C7' 115.2(2) . . ?
C3 C2 C1 103.58(18) . . ?
C7' C2 C1 111.64(19) . . ?
C3 C2 H2 108.7 . . ?
C7' C2 H2 108.7 . . ?
C1 C2 H2 108.7 . . ?
C1' C3 C2 115.8(2) . . ?
C1' C3 C4 113.80(19) . . ?
C2 C3 C4 102.27(19) . . ?
C1' C3 H3 108.2 . . ?
C2 C3 H3 108.2 . . ?
C4 C3 H3 108.2 . . ?
N5 C4 C3 102.91(19) . . ?
N5 C4 H4A 111.2 . . ?
C3 C4 H4A 111.2 . . ?
N5 C4 H4B 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
C2' C1' C6' 118.0(2) . . ?
C2' C1' C3 120.3(2) . . ?
C6' C1' C3 121.7(2) . . ?
C3' C2' C1' 121.1(3) . . ?
C3' C2' H2' 119.4 . . ?
C1' C2' H2' 119.4 . . ?
C4' C3' C2' 120.3(3) . . ?
C4' C3' H3' 119.8 . . ?
C2' C3' H3' 119.8 . . ?
C5' C4' C3' 119.2(3) . . ?
C5' C4' H4' 120.4 . . ?
C3' C4' H4' 120.4 . . ?
C4' C5' C6' 120.6(3) . . ?
C4' C5' H5' 119.7 . . ?
C6' C5' H5' 119.7 . . ?
C5' C6' C1' 120.8(3) . . ?
C5' C6' H6' 119.6 . . ?
C1' C6' H6' 119.6 . . ?
O2 C7' C8' 121.3(2) . . ?
O2 C7' C2 120.6(2) . . ?
C8' C7' C2 118.1(2) . . ?
C13' C8' C9' 118.2(2) . . ?
C13' C8' C7' 123.0(2) . . ?
C9' C8' C7' 118.8(2) . . ?
C10' C9' C8' 120.6(3) . . ?
C10' C9' H9' 119.7 . . ?
C8' C9' H9' 119.7 . . ?
C9' C10' C11' 120.5(3) . . ?
C9' C10' H10' 119.8 . . ?
C11' C10' H10' 119.8 . . ?
C12' C11' C10' 119.8(3) . . ?
C12' C11' H11' 120.1 . . ?
C10' C11' H11' 120.1 . . ?
C11' C12' C13' 119.8(3) . . ?
C11' C12' H12' 120.1 . . ?
C13' C12' H12' 120.1 . . ?
C12' C13' C8' 121.2(3) . . ?
C12' C13' H13' 119.4 . . ?
C8' C13' H13' 119.4 . . ?

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
C4 N5 C1 O1 -172.6(3) . . . . ?
C4 N5 C1 C2 5.5(3) . . . . ?
O1 C1 C2 C3 -167.1(3) . . . . ?
N5 C1 C2 C3 14.7(3) . . . . ?
O1 C1 C2 C7' -42.5(4) . . . . ?
N5 C1 C2 C7' 139.3(2) . . . . ?
C7' C2 C3 C1' 86.3(3) . . . . ?
C1 C2 C3 C1' -151.5(2) . . . . ?
C7' C2 C3 C4 -149.3(2) . . . . ?
C1 C2 C3 C4 -27.1(2) . . . . ?
C1 N5 C4 C3 -23.2(3) . . . . ?
C1' C3 C4 N5 155.8(2) . . . . ?
C2 C3 C4 N5 30.1(3) . . . . ?
C2 C3 C1' C2' -128.0(2) . . . . ?
C4 C3 C1' C2' 113.8(3) . . . . ?
C2 C3 C1' C6' 54.1(3) . . . . ?
C4 C3 C1' C6' -64.0(3) . . . . ?
C6' C1' C2' C3' 0.3(4) . . . . ?
C3 C1' C2' C3' -177.7(2) . . . . ?
C1' C2' C3' C4' -0.5(5) . . . . ?
C2' C3' C4' C5' -0.1(5) . . . . ?
C3' C4' C5' C6' 1.0(5) . . . . ?
C4' C5' C6' C1' -1.2(4) . . . . ?
C2' C1' C6' C5' 0.6(4) . . . . ?
C3 C1' C6' C5' 178.4(2) . . . . ?
C3 C2 C7' O2 13.0(3) . . . . ?
C1 C2 C7' O2 -104.8(3) . . . . ?
C3 C2 C7' C8' -168.0(2) . . . . ?
C1 C2 C7' C8' 74.2(3) . . . . ?
O2 C7' C8' C13' -149.0(3) . . . . ?
C2 C7' C8' C13' 32.1(4) . . . . ?
O2 C7' C8' C9' 28.1(4) . . . . ?
C2 C7' C8' C9' -150.8(2) . . . . ?
C13' C8' C9' C10' 0.1(4) . . . . ?
C7' C8' C9' C10' -177.1(3) . . . . ?
C8' C9' C10' C11' 1.0(5) . . . . ?
C9' C10' C11' C12' -1.1(5) . . . . ?
C10' C11' C12' C13' 0.1(5) . . . . ?
C11' C12' C13' C8' 1.0(5) . . . . ?
C9' C8' C13' C12' -1.1(4) . . . . ?
C7' C8' C13' C12' 176.1(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
N5 H5 O1 0.86 2.04 2.867(3) 161.8 2_666

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.090

_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_MD42_0m
_database_code_depnum_ccdc_archive 'CCDC 1492205'
_audit_update_record             
;
2016-07-12 deposited with the CCDC.
2017-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H15 N O3'
_chemical_formula_sum            'C13 H15 N O3'
_chemical_formula_weight         233.26

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'
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                   5.21520(7)
_cell_length_b                   9.89840(14)
_cell_length_c                   23.0406(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.5570(5)
_cell_angle_gamma                90
_cell_volume                     1185.65(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    9112
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      28.33

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.487
_exptl_crystal_size_mid          0.473
_exptl_crystal_size_min          0.449
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      250(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 PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25501
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.717
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             2073
_reflns_number_gt                1838
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0714P)²+0.3967P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    RIDING
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2073
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1264
_refine_ls_wR_factor_gt          0.1212
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 -0.2321(2) 0.60871(12) -0.00961(5) 0.0462(3) Uani 1 1 d . . . A 4
O2 O -0.1110(3) 0.89766(12) 0.07880(6) 0.0522(4) Uani 1 1 d . . . A 4
O3 O 0.5947(3) 0.72831(15) 0.34232(6) 0.0624(4) Uani 1 1 d . . . A 4
N5 N -0.3354(3) 0.51152(14) 0.07559(6) 0.0449(4) Uani 1 1 d . . . A 4
H5 H -0.4636 0.4626 0.0611 0.054 Uiso 1 1 calc R U . A 4
C1 C -0.2006(3) 0.59178(15) 0.04341(7) 0.0370(4) Uani 1 1 d . . . A 4
C2 C -0.0002(3) 0.66506(15) 0.08436(6) 0.0332(4) Uani 1 1 d . . . A 4
H2 H 0.1676 0.6183 0.0842 0.040 Uiso 1 1 calc R U . A 4
C3 C -0.1068(3) 0.64796(16) 0.14398(6) 0.0352(4) Uani 1 1 d . . . A 4
H3 H -0.2383 0.7191 0.1473 0.042 Uiso 1 1 calc R U . A 4
C4 C -0.2496(4) 0.51245(18) 0.13744(7) 0.0461(4) Uani 1 1 d . . . A 4
H4A H -0.1344 0.4364 0.1476 0.055 Uiso 1 1 calc R U . A 4
H4B H -0.3957 0.5094 0.1617 0.055 Uiso 1 1 calc R U . A 4
C1' C 0.0848(3) 0.66110(15) 0.19640(6) 0.0352(4) Uani 1 1 d . . . A 4
C2' C 0.2773(3) 0.75824(18) 0.19832(7) 0.0444(4) Uani 1 1 d . . . A 4
H2' H 0.2938 0.8129 0.1654 0.053 Uiso 1 1 calc R U . A 4
C3' C 0.4455(3) 0.77708(19) 0.24715(8) 0.0483(4) Uani 1 1 d . . . A 4
H3' H 0.5744 0.8434 0.2471 0.058 Uiso 1 1 calc R U . A 4
C4' C 0.4238(3) 0.69834(17) 0.29601(7) 0.0427(4) Uani 1 1 d . . . A 4
C5' C 0.2354(4) 0.60115(19) 0.29535(7) 0.0513(5) Uani 1 1 d . . . A 4
H5' H 0.2199 0.5466 0.3283 0.062 Uiso 1 1 calc R U . A 4
C6' C 0.0673(4) 0.58347(18) 0.24591(8) 0.0486(4) Uani 1 1 d . . . A 4
H6' H -0.0614 0.5171 0.2461 0.058 Uiso 1 1 calc R U . A 4
C7' C 0.6083(5) 0.6407(3) 0.38991(9) 0.0779(7) Uani 1 1 d . . . A 4
H7'1 H 0.4431 0.6382 0.4065 0.117 Uiso 1 1 calc R U . A 4
H7'2 H 0.7391 0.6722 0.4191 0.117 Uiso 1 1 calc R U . A 4
H7'3 H 0.6523 0.5507 0.3773 0.117 Uiso 1 1 calc R U . A 4
C8' C 0.0257(3) 0.80877(16) 0.06285(7) 0.0374(4) Uani 1 1 d . . . A 4
C9' C 0.2217(4) 0.8314(2) 0.02037(9) 0.0565(5) Uani 1 1 d . . . A 4
H9'1 H 0.1945 0.9192 0.0023 0.085 Uiso 1 1 calc R U . A 4
H9'2 H 0.2063 0.7617 -0.0093 0.085 Uiso 1 1 calc R U . A 4
H9'3 H 0.3923 0.8281 0.0404 0.085 Uiso 1 1 calc R U . A 4


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2312(19) . ?
O2 C8' 1.208(2) . ?
O3 C4' 1.367(2) . ?
O3 C7' 1.396(3) . ?
N5 C1 1.326(2) . ?
N5 C4 1.459(2) . ?
N5 H5 0.8700 . ?
C1 C2 1.534(2) . ?
C2 C8' 1.516(2) . ?
C2 C3 1.532(2) . ?
C2 H2 0.9900 . ?
C3 C1' 1.511(2) . ?
C3 C4 1.536(2) . ?
C3 H3 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C1' C6' 1.385(2) . ?
C1' C2' 1.388(2) . ?
C2' C3' 1.383(2) . ?
C2' H2' 0.9400 . ?
C3' C4' 1.381(3) . ?
C3' H3' 0.9400 . ?
C4' C5' 1.375(3) . ?
C5' C6' 1.392(2) . ?
C5' H5' 0.9400 . ?
C6' H6' 0.9400 . ?
C7' H7'1 0.9700 . ?
C7' H7'2 0.9700 . ?
C7' H7'3 0.9700 . ?
C8' C9' 1.487(2) . ?
C9' H9'1 0.9700 . ?
C9' H9'2 0.9700 . ?
C9' H9'3 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4' O3 C7' 117.89(17) . . ?
C1 N5 C4 114.04(13) . . ?
C1 N5 H5 123.0 . . ?
C4 N5 H5 123.0 . . ?
O1 C1 N5 126.99(15) . . ?
O1 C1 C2 125.21(15) . . ?
N5 C1 C2 107.77(13) . . ?
C8' C2 C1 108.46(12) . . ?
C8' C2 C3 116.43(13) . . ?
C1 C2 C3 102.78(12) . . ?
C8' C2 H2 109.6 . . ?
C1 C2 H2 109.6 . . ?
C3 C2 H2 109.6 . . ?
C1' C3 C2 116.31(13) . . ?
C1' C3 C4 116.01(13) . . ?
C2 C3 C4 102.49(12) . . ?
C1' C3 H3 107.1 . . ?
C2 C3 H3 107.1 . . ?
C4 C3 H3 107.1 . . ?
N5 C4 C3 102.12(13) . . ?
N5 C4 H4A 111.3 . . ?
C3 C4 H4A 111.3 . . ?
N5 C4 H4B 111.3 . . ?
C3 C4 H4B 111.3 . . ?
H4A C4 H4B 109.2 . . ?
C6' C1' C2' 116.93(15) . . ?
C6' C1' C3 121.89(15) . . ?
C2' C1' C3 121.06(13) . . ?
C3' C2' C1' 121.98(15) . . ?
C3' C2' H2' 119.0 . . ?
C1' C2' H2' 119.0 . . ?
C4' C3' C2' 119.95(17) . . ?
C4' C3' H3' 120.0 . . ?
C2' C3' H3' 120.0 . . ?
O3 C4' C5' 125.56(16) . . ?
O3 C4' C3' 115.04(16) . . ?
C5' C4' C3' 119.38(15) . . ?
C4' C5' C6' 120.01(16) . . ?
C4' C5' H5' 120.0 . . ?
C6' C5' H5' 120.0 . . ?
C1' C6' C5' 121.75(17) . . ?
C1' C6' H6' 119.1 . . ?
C5' C6' H6' 119.1 . . ?
O3 C7' H7'1 109.5 . . ?
O3 C7' H7'2 109.5 . . ?
H7'1 C7' H7'2 109.5 . . ?
O3 C7' H7'3 109.5 . . ?
H7'1 C7' H7'3 109.5 . . ?
H7'2 C7' H7'3 109.5 . . ?
O2 C8' C9' 122.93(15) . . ?
O2 C8' C2 120.93(15) . . ?
C9' C8' C2 116.12(14) . . ?
C8' C9' H9'1 109.5 . . ?
C8' C9' H9'2 109.5 . . ?
H9'1 C9' H9'2 109.5 . . ?
C8' C9' H9'3 109.5 . . ?
H9'1 C9' H9'3 109.5 . . ?
H9'2 C9' H9'3 109.5 . . ?

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

C4 N5 C1 C2 -2.34(18) . . . . ?
O1 C1 C2 C8' 36.1(2) . . . . ?
N5 C1 C2 C8' -142.17(13) . . . . ?
O1 C1 C2 C3 159.89(15) . . . . ?
N5 C1 C2 C3 -18.33(16) . . . . ?
C8' C2 C3 C1' -83.78(17) . . . . ?
C1 C2 C3 C1' 157.85(12) . . . . ?
C8' C2 C3 C4 148.59(13) . . . . ?
C1 C2 C3 C4 30.22(15) . . . . ?
C1 N5 C4 C3 21.89(18) . . . . ?
C1' C3 C4 N5 -159.13(13) . . . . ?
C2 C3 C4 N5 -31.31(16) . . . . ?
C2 C3 C1' C6' -144.35(16) . . . . ?
C4 C3 C1' C6' -23.7(2) . . . . ?
C2 C3 C1' C2' 39.8(2) . . . . ?
C4 C3 C1' C2' 160.48(15) . . . . ?
C6' C1' C2' C3' 0.2(3) . . . . ?
C3 C1' C2' C3' 176.25(15) . . . . ?
C1' C2' C3' C4' -0.3(3) . . . . ?
C7' O3 C4' C5' 10.7(3) . . . . ?
C7' O3 C4' C3' -170.96(19) . . . . ?
C2' C3' C4' O3 -178.07(16) . . . . ?
C2' C3' C4' C5' 0.4(3) . . . . ?
O3 C4' C5' C6' 177.83(17) . . . . ?
C3' C4' C5' C6' -0.5(3) . . . . ?
C2' C1' C6' C5' -0.3(3) . . . . ?
C3 C1' C6' C5' -176.28(16) . . . . ?
C4' C5' C6' C1' 0.4(3) . . . . ?
C1 C2 C8' O2 88.51(17) . . . . ?
C3 C2 C8' O2 -26.7(2) . . . . ?
C1 C2 C8' C9' -89.84(16) . . . . ?
C3 C2 C8' C9' 154.93(14) . . . . ?

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
C9' H9'1 O2 0.97 2.61 3.541(2) 159.9 3_575
N5 H5 O1 0.87 2.03 2.8758(17) 163.4 3_465
C9' H9'1 O2 0.97 2.61 3.541(2) 159.9 3_575
N5 H5 O1 0.87 2.03 2.8758(17) 163.4 3_465
C9' H9'1 O2 0.97 2.61 3.541(2) 159.9 3_575
N5 H5 O1 0.87 2.03 2.8758(17) 163.4 3_465
C9' H9'1 O2 0.97 2.61 3.541(2) 159.9 3_575
N5 H5 O1 0.87 2.03 2.8758(17) 163.4 3_465
C9' H9'1 O2 0.97 2.61 3.541(2) 159.9 3_575
N5 H5 O1 0.87 2.03 2.8758(17) 163.4 3_465
C9' H9'1 O2 0.97 2.61 3.541(2) 159.9 3_575
N5 H5 O1 0.87 2.03 2.8758(17) 163.4 3_465
C9' H9'1 O2 0.97 2.61 3.541(2) 159.9 3_575
N5 H5 O1 0.87 2.03 2.8758(17) 163.4 3_465
C9' H9'1 O2 0.97 2.61 3.541(2) 159.9 3_575
C9' H9'1 O2 0.97 2.61 3.541(2) 159.9 3_575
N5 H5 O1 0.87 2.03 2.8758(17) 163.4 3_465
C9' H9'1 O2 0.97 2.61 3.541(2) 159.9 3_575
N5 H5 O1 0.87 2.03 2.8758(17) 163.4 3_465
C9' H9'1 O2 0.97 2.61 3.541(2) 159.9 3_575

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.051

_shelxl_version_number           2014-3

