# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_MP132-2
_database_code_depnum_ccdc_archive 'CCDC 1976126'
loop_
_audit_author_name
_audit_author_address
'Martin Koeckerling'
;Universitaet Rostock
Germany
;
_audit_update_record             
;
2020-01-08 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;
_audit_creation_date             january-8-2020
_audit_creation_method           'ciftab-2016 (M. Köckerling, 2016)'
_chemical_melting_point_gt       487
_chemical_melting_point_lt       489
_chemical_name_systematic        
;
3-(3-(Benzyloxy)propyl)-8-bromo-1H-purine-2,6(3H,7H)-dione 
;

_chemical_formula_moiety         'C15 H15 Br N4 O3'
_chemical_formula_sum            'C15 H15 Br N4 O3'

_chemical_formula_weight         379.22


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2713 2.4705 '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                   5.5984(1)
_cell_length_b                   11.0930(2)
_cell_length_c                   12.6395(3)
_cell_angle_alpha                93.034(1)
_cell_angle_beta                 97.303(1)
_cell_angle_gamma                99.705(1)
_cell_volume                     765.22(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9905
_cell_measurement_theta_min      3.2595
_cell_measurement_theta_max      38.428

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   0.66290
_exptl_transmission_factor_max   0.74800
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    2.707
_shelx_estimated_absorpt_T_min   0.497
_shelx_estimated_absorpt_T_max   0.587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker-Nonius SADABS'

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            44798
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.259
_diffrn_reflns_theta_max         40.568
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             9784
_reflns_number_gt                7701
_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-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014-7)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+0.0510P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9784
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0808
_refine_ls_wR_factor_gt          0.0759
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.002
_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 0.4593(2) -0.43382(7) 0.34393(6) 0.0169(1) Uani 1 1 d . . . . .
C2 C 0.3891(1) -0.25499(7) 0.36693(6) 0.0154(1) Uani 1 1 d . . . . .
C3 C 0.2299(1) -0.32832(7) 0.42145(6) 0.0158(1) Uani 1 1 d . . . . .
C4 C 0.0607(1) -0.28071(7) 0.47906(6) 0.0153(1) Uani 1 1 d . . . . .
C5 C 0.2348(2) -0.07845(7) 0.41830(6) 0.0180(1) Uani 1 1 d . . . . .
C6 C 0.5739(2) -0.05329(8) 0.31104(7) 0.0192(1) Uani 1 1 d . . . . .
H6A H 0.7189 -0.0932 0.3093 0.023 Uiso 1 1 calc R U . . .
H6B H 0.6275 0.0261 0.3541 0.023 Uiso 1 1 calc R U . . .
C7 C 0.4787(2) -0.02890(9) 0.19768(7) 0.0234(2) Uani 1 1 d . . . . .
H7A H 0.3368 0.0135 0.1984 0.028 Uiso 1 1 calc R U . . .
H7B H 0.4241 -0.1076 0.1537 0.028 Uiso 1 1 calc R U . . .
C8 C 0.6802(2) 0.05023(9) 0.14968(7) 0.0264(2) Uani 1 1 d . . . . .
H8A H 0.8261 0.0103 0.1527 0.032 Uiso 1 1 calc R U . . .
H8B H 0.6238 0.0609 0.0739 0.032 Uiso 1 1 calc R U . . .
C9 C 0.9713(2) 0.23301(9) 0.19179(7) 0.0242(2) Uani 1 1 d . . . . .
H9A H 1.0985 0.1823 0.2090 0.029 Uiso 1 1 calc R U . . .
H9B H 1.0126 0.3080 0.2413 0.029 Uiso 1 1 calc R U . . .
C10 C 0.9758(2) 0.26928(8) 0.07851(7) 0.0214(1) Uani 1 1 d . . . . .
C11 C 0.8066(2) 0.3371(1) 0.03336(8) 0.0276(2) Uani 1 1 d . . . . .
H11 H 0.6848 0.3579 0.0734 0.033 Uiso 1 1 calc R U . . .
C12 C 0.8133(2) 0.3746(1) -0.06958(9) 0.0355(2) Uani 1 1 d . . . . .
H12 H 0.6969 0.4208 -0.0996 0.043 Uiso 1 1 calc R U . . .
C13 C 0.9905(2) 0.3443(1) -0.12821(8) 0.0369(3) Uani 1 1 d . . . . .
H13 H 0.9967 0.3705 -0.1983 0.044 Uiso 1 1 calc R U . . .
C14 C 1.1575(2) 0.2764(1) -0.0850(1) 0.0414(3) Uani 1 1 d . . . . .
H14 H 1.2780 0.2552 -0.1256 0.050 Uiso 1 1 calc R U . . .
C15 C 1.1504(2) 0.2384(1) 0.0183(1) 0.0347(2) Uani 1 1 d . . . . .
H15 H 1.2658 0.1912 0.0475 0.042 Uiso 1 1 calc R U . . .
N1 N 0.2784(1) -0.44533(6) 0.40514(5) 0.0166(1) Uani 1 1 d . . . . .
H1 H 0.2063 -0.5129 0.4296 0.020 Uiso 1 1 calc R U . . .
N2 N 0.5347(1) -0.32034(6) 0.31810(5) 0.0176(1) Uani 1 1 d . . . . .
N3 N 0.0776(1) -0.15535(6) 0.47155(6) 0.0179(1) Uani 1 1 d . . . . .
H3 H -0.0245 -0.1203 0.5049 0.022 Uiso 1 1 calc R U . . .
N4 N 0.3928(1) -0.13118(6) 0.36377(6) 0.0174(1) Uani 1 1 d . . . . .
O1 O -0.0888(1) -0.33569(6) 0.53144(5) 0.0204(1) Uani 1 1 d . . . . .
O2 O 0.2322(1) 0.03261(6) 0.42025(6) 0.0254(1) Uani 1 1 d . . . . .
O3 O 0.7404(1) 0.16607(6) 0.20913(6) 0.0238(1) Uani 1 1 d . . . . .
Br1 Br 0.58485(2) -0.57005(2) 0.30036(2) 0.02509(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
C1 N2 1.330(1) .
C1 N1 1.344(1) .
C1 Br1 1.8572(8) .
C2 N2 1.360(1) .
C2 N4 1.373(1) .
C2 C3 1.379(1) .
C3 N1 1.380(1) .
C3 C4 1.418(1) .
C4 O1 1.2339(9) .
C4 N3 1.387(1) .
C5 O2 1.234(1) .
C5 N4 1.373(1) .
C5 N3 1.383(1) .
C6 N4 1.469(1) .
C6 C7 1.518(1) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.519(1) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 O3 1.420(1) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 O3 1.427(1) .
C9 C10 1.510(1) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C15 1.388(1) .
C10 C11 1.392(1) .
C11 C12 1.390(2) .
C11 H11 0.9500 .
C12 C13 1.385(2) .
C12 H12 0.9500 .
C13 C14 1.375(2) .
C13 H13 0.9500 .
C14 C15 1.396(2) .
C14 H14 0.9500 .
C15 H15 0.9500 .
N1 H1 0.8800 .
N3 H3 0.8800 .

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
N2 C1 N1 114.95(7) . .
N2 C1 Br1 124.48(6) . .
N1 C1 Br1 120.57(6) . .
N2 C2 N4 125.76(7) . .
N2 C2 C3 111.94(7) . .
N4 C2 C3 122.30(7) . .
C2 C3 N1 105.39(6) . .
C2 C3 C4 122.26(7) . .
N1 C3 C4 132.35(7) . .
O1 C4 N3 119.94(7) . .
O1 C4 C3 128.64(7) . .
N3 C4 C3 111.42(6) . .
O2 C5 N4 121.84(7) . .
O2 C5 N3 121.05(8) . .
N4 C5 N3 117.11(7) . .
N4 C6 C7 113.64(7) . .
N4 C6 H6A 108.8 . .
C7 C6 H6A 108.8 . .
N4 C6 H6B 108.8 . .
C7 C6 H6B 108.8 . .
H6A C6 H6B 107.7 . .
C6 C7 C8 109.57(7) . .
C6 C7 H7A 109.8 . .
C8 C7 H7A 109.8 . .
C6 C7 H7B 109.8 . .
C8 C7 H7B 109.8 . .
H7A C7 H7B 108.2 . .
O3 C8 C7 108.44(8) . .
O3 C8 H8A 110.0 . .
C7 C8 H8A 110.0 . .
O3 C8 H8B 110.0 . .
C7 C8 H8B 110.0 . .
H8A C8 H8B 108.4 . .
O3 C9 C10 113.29(8) . .
O3 C9 H9A 108.9 . .
C10 C9 H9A 108.9 . .
O3 C9 H9B 108.9 . .
C10 C9 H9B 108.9 . .
H9A C9 H9B 107.7 . .
C15 C10 C11 118.74(9) . .
C15 C10 C9 121.12(9) . .
C11 C10 C9 120.13(8) . .
C12 C11 C10 120.8(1) . .
C12 C11 H11 119.6 . .
C10 C11 H11 119.6 . .
C13 C12 C11 119.7(1) . .
C13 C12 H12 120.1 . .
C11 C12 H12 120.1 . .
C14 C13 C12 120.1(1) . .
C14 C13 H13 120.0 . .
C12 C13 H13 120.0 . .
C13 C14 C15 120.2(1) . .
C13 C14 H14 119.9 . .
C15 C14 H14 119.9 . .
C10 C15 C14 120.4(1) . .
C10 C15 H15 119.8 . .
C14 C15 H15 119.8 . .
C1 N1 C3 105.19(6) . .
C1 N1 H1 127.4 . .
C3 N1 H1 127.4 . .
C1 N2 C2 102.54(6) . .
C5 N3 C4 128.20(7) . .
C5 N3 H3 115.9 . .
C4 N3 H3 115.9 . .
C2 N4 C5 118.69(6) . .
C2 N4 C6 121.50(7) . .
C5 N4 C6 119.62(7) . .
C8 O3 C9 112.46(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
N2 C2 C3 N1 -0.31(9) . . . .
N4 C2 C3 N1 179.25(7) . . . .
N2 C2 C3 C4 179.70(7) . . . .
N4 C2 C3 C4 -0.7(1) . . . .
C2 C3 C4 O1 -179.33(8) . . . .
N1 C3 C4 O1 0.7(2) . . . .
C2 C3 C4 N3 0.6(1) . . . .
N1 C3 C4 N3 -179.39(8) . . . .
N4 C6 C7 C8 -179.02(8) . . . .
C6 C7 C8 O3 -64.2(1) . . . .
O3 C9 C10 C15 -125.4(1) . . . .
O3 C9 C10 C11 56.0(1) . . . .
C15 C10 C11 C12 -0.8(2) . . . .
C9 C10 C11 C12 177.9(1) . . . .
C10 C11 C12 C13 0.0(2) . . . .
C11 C12 C13 C14 0.6(2) . . . .
C12 C13 C14 C15 -0.5(2) . . . .
C11 C10 C15 C14 0.9(2) . . . .
C9 C10 C15 C14 -177.7(1) . . . .
C13 C14 C15 C10 -0.3(2) . . . .
N2 C1 N1 C3 -0.1(1) . . . .
Br1 C1 N1 C3 -179.59(6) . . . .
C2 C3 N1 C1 0.24(9) . . . .
C4 C3 N1 C1 -179.78(9) . . . .
N1 C1 N2 C2 -0.09(9) . . . .
Br1 C1 N2 C2 179.38(6) . . . .
N4 C2 N2 C1 -179.30(8) . . . .
C3 C2 N2 C1 0.25(9) . . . .
O2 C5 N3 C4 -178.58(8) . . . .
N4 C5 N3 C4 1.3(1) . . . .
O1 C4 N3 C5 179.01(8) . . . .
C3 C4 N3 C5 -0.9(1) . . . .
N2 C2 N4 C5 -179.45(8) . . . .
C3 C2 N4 C5 1.0(1) . . . .
N2 C2 N4 C6 -4.4(1) . . . .
C3 C2 N4 C6 176.08(7) . . . .
O2 C5 N4 C2 178.63(8) . . . .
N3 C5 N4 C2 -1.2(1) . . . .
O2 C5 N4 C6 3.5(1) . . . .
N3 C5 N4 C6 -176.37(7) . . . .
C7 C6 N4 C2 97.4(1) . . . .
C7 C6 N4 C5 -87.6(1) . . . .
C7 C8 O3 C9 162.63(8) . . . .
C10 C9 O3 C8 65.2(1) . . . .

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 H9B Br1 0.99 3.09 3.656(1) 117.5 1_565
N1 H1 O1 0.88 1.81 2.6875(9) 171.0 2_546
N3 H3 O2 0.88 1.94 2.817(1) 175.9 2_556
_refine_diff_density_max         0.873
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.083

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_HW26-14
_database_code_depnum_ccdc_archive 'CCDC 1976810'
loop_
_audit_author_name
_audit_author_address
'Martin Koeckerling'
;Universitaet Rostock
Germany
;
_audit_update_record             
;
2020-01-10 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;
_audit_creation_date             january-10-2020
_audit_creation_method           'ciftab-2016 (M. Köckerling, 2016)'

_chemical_name_systematic        
;
1-(3-(Methoxy)propyl)urea
;

_chemical_formula_moiety         'C10 H24 N4 O4'
_chemical_formula_sum            'C10 H24 N4 O4'

_chemical_formula_weight         264.33


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 '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                   10.3000(6)
_cell_length_b                   7.5991(6)
_cell_length_c                   9.0926(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.806(4)
_cell_angle_gamma                90
_cell_volume                     708.03(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4657
_cell_measurement_theta_min      3.3365
_cell_measurement_theta_max      27.3885

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   0.53870
_exptl_transmission_factor_max   0.74560
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker-Nonius SADABS'

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            11184
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.338
_diffrn_reflns_theta_max         27.635
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1639
_reflns_number_gt                1400
_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-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0422P)²+0.1440P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1639
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0940
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
N1 N 0.44090(9) 0.8996(1) 0.66822(9) 0.0335(2) Uani 1 1 d . . . . .
H1A H 0.4915 0.9855 0.6431 0.040 Uiso 1 1 calc R U . . .
H1B H 0.4334 0.8784 0.7621 0.040 Uiso 1 1 calc R U . . .
C1 C 0.37499(9) 0.8006(1) 0.5630(1) 0.0241(2) Uani 1 1 d . . . . .
O1 O 0.38335(7) 0.8270(1) 0.42851(7) 0.0302(2) Uani 1 1 d . . . . .
N2 N 0.29960(9) 0.6728(1) 0.61116(9) 0.0315(2) Uani 1 1 d . . . . .
H2A H 0.2959 0.6609 0.7069 0.038 Uiso 1 1 calc R U . . .
C2 C 0.2239(1) 0.5536(1) 0.5112(1) 0.0299(2) Uani 1 1 d . . . . .
H2B H 0.2046 0.6119 0.4141 0.036 Uiso 1 1 calc R U . . .
H2C H 0.1397 0.5289 0.5509 0.036 Uiso 1 1 calc R U . . .
C3 C 0.2932(1) 0.3810(2) 0.4895(1) 0.0313(2) Uani 1 1 d . . . . .
H3A H 0.3789 0.4055 0.4534 0.038 Uiso 1 1 calc R U . . .
H3B H 0.3092 0.3200 0.5858 0.038 Uiso 1 1 calc R U . . .
C4 C 0.2154(1) 0.2618(2) 0.3807(1) 0.0346(3) Uani 1 1 d . . . . .
H4A H 0.2011 0.3199 0.2830 0.041 Uiso 1 1 calc R U . . .
H4B H 0.2638 0.1509 0.3691 0.041 Uiso 1 1 calc R U . . .
O2 O 0.09391(8) 0.2250(1) 0.43415(9) 0.0421(2) Uani 1 1 d . . . . .
C5 C 0.0177(1) 0.1121(2) 0.3363(2) 0.0546(4) Uani 1 1 d . . . . .
H5A H -0.0658 0.0886 0.3754 0.082 Uiso 1 1 calc R U . . .
H5B H 0.0644 0.0011 0.3264 0.082 Uiso 1 1 calc R U . . .
H5C H 0.0017 0.1685 0.2392 0.082 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
N1 C1 1.345(1) .
N1 H1A 0.8800 .
N1 H1B 0.8800 .
C1 O1 1.251(1) .
C1 N2 1.344(1) .
N2 C2 1.453(1) .
N2 H2A 0.8800 .
C2 C3 1.516(2) .
C2 H2B 0.9900 .
C2 H2C 0.9900 .
C3 C4 1.511(2) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 O2 1.415(1) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
O2 C5 1.415(1) .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .

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
C1 N1 H1A 120.0 . .
C1 N1 H1B 120.0 . .
H1A N1 H1B 120.0 . .
O1 C1 N2 122.25(9) . .
O1 C1 N1 121.70(9) . .
N2 C1 N1 116.06(8) . .
C1 N2 C2 122.57(8) . .
C1 N2 H2A 118.7 . .
C2 N2 H2A 118.7 . .
N2 C2 C3 113.00(8) . .
N2 C2 H2B 109.0 . .
C3 C2 H2B 109.0 . .
N2 C2 H2C 109.0 . .
C3 C2 H2C 109.0 . .
H2B C2 H2C 107.8 . .
C4 C3 C2 112.24(9) . .
C4 C3 H3A 109.2 . .
C2 C3 H3A 109.2 . .
C4 C3 H3B 109.2 . .
C2 C3 H3B 109.2 . .
H3A C3 H3B 107.9 . .
O2 C4 C3 108.83(8) . .
O2 C4 H4A 109.9 . .
C3 C4 H4A 109.9 . .
O2 C4 H4B 109.9 . .
C3 C4 H4B 109.9 . .
H4A C4 H4B 108.3 . .
C4 O2 C5 110.92(9) . .
O2 C5 H5A 109.5 . .
O2 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
O2 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 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
O1 C1 N2 C2 1.1(2) . . . .
N1 C1 N2 C2 -179.18(9) . . . .
C1 N2 C2 C3 95.7(1) . . . .
N2 C2 C3 C4 -177.74(8) . . . .
C2 C3 C4 O2 -59.8(1) . . . .
C3 C4 O2 C5 -179.5(1) . . . .
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.033

_shelxl_version_number           2014-1

