# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_4g
_database_code_depnum_ccdc_archive 'CCDC 1911715'
loop_
_audit_author_name
_audit_author_address
'Royston Copley'
;GlaxoSmithKline
United Kingdom
;
_audit_update_record             
;
2019-04-23 deposited with the CCDC.	2019-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
; 
Ethyl 2-amino-5-isobutyl-1H-imidazole-4-carboxylate 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H17 N3 O2'
_chemical_formula_sum            'C10 H17 N3 O2'
_chemical_formula_weight         211.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.7186(3)
_cell_length_b                   11.7583(4)
_cell_length_c                   20.8375(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.0696(10)
_cell_angle_gamma                90
_cell_volume                     2367.84(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9903
_cell_measurement_theta_min      5.25
_cell_measurement_theta_max      66.58

_exptl_crystal_description       Lath
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   0.6439
_exptl_transmission_factor_max   1.0000
_exptl_crystal_size_max          0.593
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.066
_exptl_absorpt_coefficient_mu    0.688
_shelx_estimated_absorpt_T_min   0.686
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8086
_exptl_absorpt_correction_T_max  0.9617
_exptl_absorpt_process_details   
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            37770
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.267
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_full        66.601
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4186
_reflns_number_gt                3803
_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 Instrument Service v6.2.6'
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_merging          SHELXL
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker XP, PLATON, and CSD Mercury'
_computing_publication_material  'SHELXL, XCIF, and local software'
_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)+(0.0694P)²+0.4644P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4186
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1153
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_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 0.87543(9) 0.70699(8) 0.72830(5) 0.0280(2) Uani 1 1 d . . . . .
H1 H 0.7939(16) 0.7318(12) 0.7325(7) 0.036(3) Uiso 1 1 d . . . . .
C2 C 0.99565(10) 0.75376(9) 0.75481(5) 0.0274(2) Uani 1 1 d . . . . .
N3 N 1.10424(8) 0.69375(8) 0.74268(5) 0.0278(2) Uani 1 1 d . . . . .
C4 C 1.04858(10) 0.60321(9) 0.70460(5) 0.0270(2) Uani 1 1 d . . . . .
C5 C 0.90689(10) 0.61112(9) 0.69537(5) 0.0268(2) Uani 1 1 d . . . . .
N6 N 0.99546(10) 0.85052(9) 0.79184(5) 0.0343(2) Uani 1 1 d . . . . .
H6A H 1.0756(16) 0.8877(13) 0.7966(7) 0.039(4) Uiso 1 1 d . . . . .
H6B H 0.9223(17) 0.8929(15) 0.7789(7) 0.050(4) Uiso 1 1 d . . . . .
C7 C 1.13961(10) 0.51789(9) 0.68138(5) 0.0280(2) Uani 1 1 d . . . . .
O8 O 1.26359(7) 0.51146(7) 0.69689(4) 0.0330(2) Uani 1 1 d . . . . .
O9 O 1.07057(8) 0.44593(7) 0.63950(4) 0.0358(2) Uani 1 1 d . . . . .
C10 C 1.15045(13) 0.35942(11) 0.61063(6) 0.0396(3) Uani 1 1 d . . . . .
H10A H 1.191630 0.305828 0.643929 0.047 Uiso 1 1 calc R U . . .
H10B H 1.225869 0.394583 0.589044 0.047 Uiso 1 1 calc R U . . .
C11 C 1.05086(16) 0.29862(13) 0.56238(7) 0.0513(4) Uani 1 1 d . . . . .
H11A H 1.009866 0.353057 0.530243 0.077 Uiso 1 1 calc R U . . .
H11B H 0.977553 0.263630 0.584571 0.077 Uiso 1 1 calc R U . . .
H11C H 1.100140 0.239473 0.540816 0.077 Uiso 1 1 calc R U . . .
C12 C 0.79634(10) 0.54150(10) 0.65883(6) 0.0318(3) Uani 1 1 d . . . . .
H12A H 0.708970 0.551944 0.678615 0.038 Uiso 1 1 calc R U . . .
H12B H 0.822170 0.460190 0.663043 0.038 Uiso 1 1 calc R U . . .
C13 C 0.77096(12) 0.57155(12) 0.58686(6) 0.0410(3) Uani 1 1 d . . . . .
H13 H 0.861336 0.566289 0.568133 0.049 Uiso 1 1 calc R U . . .
C14 C 0.71671(18) 0.69213(16) 0.57675(8) 0.0622(4) Uani 1 1 d . . . . .
H14A H 0.628964 0.699721 0.595602 0.093 Uiso 1 1 calc R U . . .
H14B H 0.701898 0.708577 0.530430 0.093 Uiso 1 1 calc R U . . .
H14C H 0.784297 0.745849 0.597704 0.093 Uiso 1 1 calc R U . . .
C15 C 0.67266(18) 0.48395(19) 0.55291(8) 0.0708(5) Uani 1 1 d . . . . .
H15A H 0.713896 0.408037 0.558276 0.106 Uiso 1 1 calc R U . . .
H15B H 0.656479 0.502266 0.506844 0.106 Uiso 1 1 calc R U . . .
H15C H 0.584526 0.485325 0.571804 0.106 Uiso 1 1 calc R U . . .
N21 N 0.37630(9) 0.76205(8) 0.72969(5) 0.0271(2) Uani 1 1 d . . . . .
H21 H 0.2974(15) 0.7376(11) 0.7350(6) 0.029(3) Uiso 1 1 d . . . . .
C22 C 0.49821(10) 0.71769(9) 0.75576(5) 0.0270(2) Uani 1 1 d . . . . .
N23 N 0.60480(8) 0.77823(8) 0.74143(5) 0.0275(2) Uani 1 1 d . . . . .
C24 C 0.54565(10) 0.86652(9) 0.70258(5) 0.0270(2) Uani 1 1 d . . . . .
C25 C 0.40400(10) 0.85650(9) 0.69489(5) 0.0264(2) Uani 1 1 d . . . . .
N26 N 0.50173(10) 0.62309(9) 0.79454(5) 0.0337(2) Uani 1 1 d . . . . .
H26A H 0.5809(15) 0.5885(12) 0.7991(6) 0.033(3) Uiso 1 1 d . . . . .
H26B H 0.4302(16) 0.5769(14) 0.7833(7) 0.046(4) Uiso 1 1 d . . . . .
C27 C 0.63269(10) 0.95316(9) 0.67780(5) 0.0288(3) Uani 1 1 d . . . . .
O28 O 0.75697(7) 0.96214(7) 0.69150(4) 0.0353(2) Uani 1 1 d . . . . .
O29 O 0.55854(8) 1.02368(7) 0.63686(4) 0.0371(2) Uani 1 1 d . . . . .
C30 C 0.63161(13) 1.11296(11) 0.60683(7) 0.0414(3) Uani 1 1 d . . . . .
H30A H 0.704991 1.080425 0.582849 0.050 Uiso 1 1 calc R U . . .
H30B H 0.674713 1.166306 0.639803 0.050 Uiso 1 1 calc R U . . .
C31 C 0.52504(16) 1.17304(13) 0.56159(7) 0.0516(4) Uani 1 1 d . . . . .
H31A H 0.453677 1.205207 0.586124 0.077 Uiso 1 1 calc R U . . .
H31B H 0.482482 1.118842 0.529711 0.077 Uiso 1 1 calc R U . . .
H31C H 0.569401 1.234291 0.539406 0.077 Uiso 1 1 calc R U . . .
C32 C 0.28976(10) 0.92153(10) 0.65779(6) 0.0308(3) Uani 1 1 d . . . . .
H32A H 0.311623 1.003714 0.660858 0.037 Uiso 1 1 calc R U . . .
H32B H 0.203154 0.909000 0.677886 0.037 Uiso 1 1 calc R U . . .
C33 C 0.26570(12) 0.88789(12) 0.58617(6) 0.0392(3) Uani 1 1 d . . . . .
H33 H 0.353187 0.902460 0.566210 0.047 Uiso 1 1 calc R U . . .
C34 C 0.22999(16) 0.76262(14) 0.57757(7) 0.0545(4) Uani 1 1 d . . . . .
H34A H 0.306171 0.716409 0.598169 0.082 Uiso 1 1 calc R U . . .
H34B H 0.215430 0.744545 0.531443 0.082 Uiso 1 1 calc R U . . .
H34C H 0.145344 0.746122 0.597564 0.082 Uiso 1 1 calc R U . . .
C35 C 0.15299(18) 0.96208(18) 0.55212(8) 0.0698(5) Uani 1 1 d . . . . .
H35A H 0.066958 0.951184 0.572006 0.105 Uiso 1 1 calc R U . . .
H35B H 0.138159 0.940929 0.506420 0.105 Uiso 1 1 calc R U . . .
H35C H 0.181008 1.042061 0.555933 0.105 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
N1 C2 1.3551(14) . yes
N1 C5 1.3709(15) . yes
N1 H1 0.857(15) . ?
C2 N3 1.3159(14) . yes
C2 N6 1.3748(15) . yes
N3 C4 1.4017(14) . yes
C4 C5 1.3733(14) . yes
C4 C7 1.4539(15) . yes
C5 C12 1.4937(15) . yes
N6 H6A 0.890(16) . ?
N6 H6B 0.887(17) . ?
C7 O8 1.2164(13) . yes
C7 O9 1.3430(14) . yes
O9 C10 1.4485(14) . yes
C10 C11 1.5010(18) . yes
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.5351(17) . yes
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.519(2) . yes
C13 C15 1.527(2) . yes
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N21 C22 1.3546(14) . yes
N21 C25 1.3685(15) . yes
N21 H21 0.837(14) . ?
C22 N23 1.3170(14) . yes
C22 N26 1.3731(15) . yes
N23 C24 1.4019(14) . yes
C24 C25 1.3741(14) . yes
C24 C27 1.4534(15) . yes
C25 C32 1.4945(14) . yes
N26 H26A 0.866(15) . ?
N26 H26B 0.894(17) . ?
C27 O28 1.2159(13) . yes
C27 O29 1.3434(14) . yes
O29 C30 1.4463(14) . yes
C30 C31 1.5013(19) . yes
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.5378(17) . yes
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C35 1.5165(19) . yes
C33 C34 1.519(2) . yes
C33 H33 1.0000 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 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
_geom_angle_publ_flag
C2 N1 C5 108.02(9) . . yes
C2 N1 H1 125.9(10) . . ?
C5 N1 H1 126.1(10) . . ?
N3 C2 N1 112.24(10) . . yes
N3 C2 N6 126.89(10) . . yes
N1 C2 N6 120.82(10) . . yes
C2 N3 C4 104.28(8) . . yes
C5 C4 N3 110.43(9) . . yes
C5 C4 C7 129.54(10) . . yes
N3 C4 C7 120.03(9) . . yes
N1 C5 C4 105.01(9) . . yes
N1 C5 C12 121.29(9) . . yes
C4 C5 C12 133.70(10) . . yes
C2 N6 H6A 114.6(9) . . ?
C2 N6 H6B 110.1(10) . . ?
H6A N6 H6B 115.0(14) . . ?
O8 C7 O9 123.11(10) . . yes
O8 C7 C4 125.10(10) . . yes
O9 C7 C4 111.79(9) . . yes
C7 O9 C10 117.35(9) . . yes
O9 C10 C11 106.07(10) . . yes
O9 C10 H10A 110.5 . . ?
C11 C10 H10A 110.5 . . ?
O9 C10 H10B 110.5 . . ?
C11 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C12 C13 113.86(10) . . yes
C5 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
C5 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C15 111.99(13) . . yes
C14 C13 C12 111.57(12) . . yes
C15 C13 C12 108.99(12) . . yes
C14 C13 H13 108.0 . . ?
C15 C13 H13 108.0 . . ?
C12 C13 H13 108.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C22 N21 C25 108.20(9) . . yes
C22 N21 H21 126.1(9) . . ?
C25 N21 H21 125.7(9) . . ?
N23 C22 N21 112.12(10) . . yes
N23 C22 N26 126.87(10) . . yes
N21 C22 N26 120.95(10) . . yes
C22 N23 C24 104.30(8) . . yes
C25 C24 N23 110.39(10) . . yes
C25 C24 C27 129.22(10) . . yes
N23 C24 C27 120.38(9) . . yes
N21 C25 C24 104.99(9) . . yes
N21 C25 C32 120.81(9) . . yes
C24 C25 C32 134.17(10) . . yes
C22 N26 H26A 114.3(9) . . ?
C22 N26 H26B 111.6(10) . . ?
H26A N26 H26B 113.6(14) . . ?
O28 C27 O29 123.25(10) . . yes
O28 C27 C24 125.34(10) . . yes
O29 C27 C24 111.40(9) . . yes
C27 O29 C30 117.89(9) . . yes
O29 C30 C31 105.99(10) . . yes
O29 C30 H30A 110.5 . . ?
C31 C30 H30A 110.5 . . ?
O29 C30 H30B 110.5 . . ?
C31 C30 H30B 110.5 . . ?
H30A C30 H30B 108.7 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C25 C32 C33 113.51(9) . . yes
C25 C32 H32A 108.9 . . ?
C33 C32 H32A 108.9 . . ?
C25 C32 H32B 108.9 . . ?
C33 C32 H32B 108.9 . . ?
H32A C32 H32B 107.7 . . ?
C35 C33 C34 110.97(13) . . yes
C35 C33 C32 109.53(11) . . yes
C34 C33 C32 111.91(11) . . yes
C35 C33 H33 108.1 . . ?
C34 C33 H33 108.1 . . ?
C32 C33 H33 108.1 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 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
C5 N1 C2 N3 -1.34(13) . . . . yes
C5 N1 C2 N6 -178.85(10) . . . . yes
N1 C2 N3 C4 1.11(12) . . . . yes
N6 C2 N3 C4 178.44(11) . . . . yes
C2 N3 C4 C5 -0.50(12) . . . . yes
C2 N3 C4 C7 179.78(10) . . . . yes
C2 N1 C5 C4 0.93(12) . . . . yes
C2 N1 C5 C12 -178.17(10) . . . . yes
N3 C4 C5 N1 -0.27(12) . . . . yes
C7 C4 C5 N1 179.41(11) . . . . yes
N3 C4 C5 C12 178.66(11) . . . . yes
C7 C4 C5 C12 -1.7(2) . . . . yes
C5 C4 C7 O8 -172.69(11) . . . . yes
N3 C4 C7 O8 6.97(17) . . . . yes
C5 C4 C7 O9 7.91(17) . . . . yes
N3 C4 C7 O9 -172.43(9) . . . . yes
O8 C7 O9 C10 -1.90(16) . . . . yes
C4 C7 O9 C10 177.52(10) . . . . yes
C7 O9 C10 C11 -175.25(10) . . . . yes
N1 C5 C12 C13 95.02(13) . . . . yes
C4 C5 C12 C13 -83.77(16) . . . . yes
C5 C12 C13 C14 -64.28(14) . . . . yes
C5 C12 C13 C15 171.54(12) . . . . yes
C25 N21 C22 N23 1.26(13) . . . . yes
C25 N21 C22 N26 178.61(10) . . . . yes
N21 C22 N23 C24 -0.91(12) . . . . yes
N26 C22 N23 C24 -178.07(11) . . . . yes
C22 N23 C24 C25 0.24(12) . . . . yes
C22 N23 C24 C27 179.05(10) . . . . yes
C22 N21 C25 C24 -1.02(12) . . . . yes
C22 N21 C25 C32 177.30(10) . . . . yes
N23 C24 C25 N21 0.48(12) . . . . yes
C27 C24 C25 N21 -178.19(11) . . . . yes
N23 C24 C25 C32 -177.50(11) . . . . yes
C27 C24 C25 C32 3.8(2) . . . . yes
C25 C24 C27 O28 172.91(11) . . . . yes
N23 C24 C27 O28 -5.65(17) . . . . yes
C25 C24 C27 O29 -7.33(17) . . . . yes
N23 C24 C27 O29 174.11(9) . . . . yes
O28 C27 O29 C30 1.31(17) . . . . yes
C24 C27 O29 C30 -178.45(10) . . . . yes
C27 O29 C30 C31 176.98(11) . . . . yes
N21 C25 C32 C33 -96.04(12) . . . . yes
C24 C25 C32 C33 81.69(16) . . . . yes
C25 C32 C33 C35 -177.33(12) . . . . yes
C25 C32 C33 C34 59.18(14) . . . . yes

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 N23 0.857(15) 1.945(15) 2.8011(12) 176.3(14) . yes
N6 H6A O8 0.890(16) 2.129(16) 3.0006(13) 166.2(13) 2_756 yes
N6 H6B O28 0.887(17) 2.438(17) 3.2313(13) 149.1(13) . yes
N21 H21 N3 0.837(14) 1.970(15) 2.8037(12) 174.2(13) 1_455 yes
N26 H26A O28 0.866(15) 2.160(15) 3.0036(12) 164.5(13) 2_646 yes
N26 H26B O8 0.894(17) 2.416(16) 3.1974(13) 146.1(13) 1_455 yes

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.041

_diffrn_source_type              'Incoatec microfocus 3.0 (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_collimation    'focussed source'

_diffrn_orient_matrix_type       'Bruker AXS Inc. convention APEX3'
_diffrn_orient_matrix_UB_11      -1.6971240e-002
_diffrn_orient_matrix_UB_12      5.5345014e-002
_diffrn_orient_matrix_UB_13      3.4740932e-002
_diffrn_orient_matrix_UB_21      2.9391903e-002
_diffrn_orient_matrix_UB_22      -5.8558222e-002
_diffrn_orient_matrix_UB_23      3.3471033e-002
_diffrn_orient_matrix_UB_31      9.7751379e-002
_diffrn_orient_matrix_UB_32      2.7216097e-002
_diffrn_orient_matrix_UB_33      1.3692902e-003

_diffrn_measurement_details      
;
Collection strategy, angles in degrees, time in seconds
Scan_type dx 2theta omega phi chi exposure_time width scan_range direction
#=============================================================================
Fast    65.000    0.000    0.000    0.000  54.781   1.000   1.000
Omega   65.000   82.960 -111.941   90.000  54.740  12.800   0.800 210.400 pos
Omega   65.000   70.337 -124.564 -104.000  54.740  10.100   0.800 210.400 pos
Omega   65.000  112.960  -81.941  -36.000  54.740  24.000   0.800 210.400 pos
Omega   65.000  112.960  -81.941 -144.000  54.740  24.000   0.800 210.400 pos
Omega   65.000  -32.188 -227.089 -160.000  54.740   6.000   0.800 210.400 pos
Omega   65.000  112.960  -81.941    0.000  54.740  24.000   0.800 210.400 pos
Omega   65.000  112.960  -81.941  135.000  54.740  24.000   0.800 210.400 pos
Phi     65.000  112.960  -82.540  -70.601  54.781  24.000   0.800 260.800 pos
Omega   65.000  112.960  -81.941   54.000  54.740  24.000   0.800 210.400 pos
Omega   65.000  -55.337 -250.238  180.000  54.740   7.800   0.800 210.400 pos
Omega   65.000  -55.337 -250.238    0.000  54.740   7.800   0.800 210.400 pos
Omega   65.000  112.960  -81.941  108.000  54.740  24.000   0.800 210.400 pos
Omega   65.000   70.337 -124.564   96.000  54.740  10.100   0.800 210.400 pos
Omega   65.000  112.960  -81.941   27.000  54.740  24.000   0.800 210.400 pos
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0330
0 0 -1 0.0290
-1 0 0 0.2910
0 1 0 0.0660
0 -1 -1 0.0710
1 0 -2 0.1550
-1 1 1 0.2480
1 2 1 0.1340
0 1 2 0.0460
1 -1 -2 0.1570
1 1 -2 0.1410
0 1 -2 0.0500
0 -1 2 0.0700

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol and water'
####################################################################### 
# 
# 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_4h
_database_code_depnum_ccdc_archive 'CCDC 1911716'
loop_
_audit_author_name
_audit_author_address
'Royston Copley'
;GlaxoSmithKline
United Kingdom
;
_audit_update_record             
;
2019-04-23 deposited with the CCDC.	2019-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
; 
Ethyl 2-amino-5-neopentyl-1H-imidazole-4-carboxylate 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H19 N3 O2'
_chemical_formula_sum            'C11 H19 N3 O2'
_chemical_formula_weight         225.29

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      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   11.6022(7)
_cell_length_b                   22.9041(13)
_cell_length_c                   9.5733(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2544.0(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9955
_cell_measurement_theta_min      4.27
_cell_measurement_theta_max      66.65

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   0.6412
_exptl_transmission_factor_max   1.0000
_exptl_crystal_size_max          0.886
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.669
_shelx_estimated_absorpt_T_min   0.589
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7992
_exptl_absorpt_correction_T_max  0.9779
_exptl_absorpt_process_details   
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            50345
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.860
_diffrn_reflns_theta_max         66.660
_diffrn_reflns_theta_full        66.660
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2252
_reflns_number_gt                2195
_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 Instrument Service v6.2.6'
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_merging          SHELXL
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker XP, PLATON, and CSD Mercury'
_computing_publication_material  'SHELXL, XCIF, and local software'
_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)+(0.0728P)²+4.3310P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2252
_refine_ls_number_parameters     161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_ref         0.1896
_refine_ls_wR_factor_gt          0.1892
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_restrained_S_all      1.151
_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 0.28434(17) 0.53346(10) 0.3758(2) 0.0264(5) Uani 1 1 d . . . . .
H1 H 0.256(3) 0.5290(15) 0.280(4) 0.050(10) Uiso 1 1 d . . . . .
C2 C 0.2397(2) 0.50868(11) 0.4918(3) 0.0271(6) Uani 1 1 d . . . . .
N3 N 0.30324(18) 0.51770(10) 0.6032(2) 0.0263(5) Uani 1 1 d . . . . .
C4 C 0.3967(2) 0.55088(11) 0.5536(3) 0.0247(6) Uani 1 1 d . . . . .
C5 C 0.3859(2) 0.56115(11) 0.4127(3) 0.0246(6) Uani 1 1 d . . . . .
N6 N 0.1405(2) 0.47608(12) 0.4847(3) 0.0344(6) Uani 1 1 d . . . . .
H6A H 0.108(3) 0.4683(15) 0.574(4) 0.043(9) Uiso 1 1 d . . . . .
H6B H 0.096(3) 0.4877(16) 0.420(4) 0.053(11) Uiso 1 1 d . . . . .
C7 C 0.4882(2) 0.56586(11) 0.6509(3) 0.0258(6) Uani 1 1 d . . . . .
O8 O 0.49051(16) 0.55137(9) 0.77358(18) 0.0310(5) Uani 1 1 d . . . . .
O9 O 0.57122(16) 0.59894(9) 0.59171(19) 0.0356(5) Uani 1 1 d . . . . .
C10 C 0.6672(3) 0.61667(14) 0.6796(3) 0.0418(7) Uani 1 1 d . . . . .
H10A H 0.735388 0.624362 0.620235 0.050 Uiso 1 1 calc R U . . .
H10B H 0.686771 0.584467 0.744315 0.050 Uiso 1 1 calc R U . . .
C11 C 0.6397(4) 0.66953(19) 0.7610(5) 0.0662(11) Uani 1 1 d . . . . .
H11A H 0.622110 0.701763 0.697162 0.099 Uiso 1 1 calc R U . . .
H11B H 0.705944 0.680052 0.819325 0.099 Uiso 1 1 calc R U . . .
H11C H 0.572749 0.661904 0.820741 0.099 Uiso 1 1 calc R U . . .
C12 C 0.4551(2) 0.59228(12) 0.3042(3) 0.0286(6) Uani 1 1 d . . . . .
H12A H 0.452074 0.569109 0.216995 0.034 Uiso 1 1 calc R U . . .
H12B H 0.536425 0.593129 0.335360 0.034 Uiso 1 1 calc R U . . .
C13 C 0.4179(3) 0.65548(12) 0.2698(3) 0.0333(7) Uani 1 1 d . . . . .
C14 C 0.2915(3) 0.65733(15) 0.2253(5) 0.0627(11) Uani 1 1 d . . . . .
H14A H 0.278793 0.629374 0.149403 0.094 Uiso 1 1 calc R U . . .
H14B H 0.272178 0.696734 0.193090 0.094 Uiso 1 1 calc R U . . .
H14C H 0.242541 0.647065 0.305040 0.094 Uiso 1 1 calc R U . . .
C15 C 0.4929(4) 0.67557(17) 0.1472(4) 0.0641(11) Uani 1 1 d . . . . .
H15A H 0.574254 0.674451 0.174745 0.096 Uiso 1 1 calc R U . . .
H15B H 0.471842 0.715554 0.121181 0.096 Uiso 1 1 calc R U . . .
H15C H 0.480728 0.649572 0.067255 0.096 Uiso 1 1 calc R U . . .
C16 C 0.4361(3) 0.69586(14) 0.3931(3) 0.0494(9) Uani 1 1 d . . . . .
H16A H 0.390085 0.682209 0.472484 0.074 Uiso 1 1 calc R U . . .
H16B H 0.412230 0.735510 0.367782 0.074 Uiso 1 1 calc R U . . .
H16C H 0.517871 0.695984 0.418871 0.074 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
N1 C2 1.351(3) . yes
N1 C5 1.384(3) . yes
N1 H1 0.98(4) . ?
C2 N3 1.313(3) . yes
C2 N6 1.373(4) . yes
N3 C4 1.406(3) . yes
C4 C5 1.374(3) . yes
C4 C7 1.454(3) . yes
C5 C12 1.494(3) . yes
N6 H6A 0.95(4) . ?
N6 H6B 0.85(4) . ?
C7 O8 1.221(3) . yes
C7 O9 1.350(3) . yes
O9 C10 1.453(3) . yes
C10 C11 1.475(5) . yes
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.546(4) . yes
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C16 1.515(4) . yes
C13 C14 1.527(5) . yes
C13 C15 1.532(4) . yes
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
_geom_angle_publ_flag
C2 N1 C5 108.0(2) . . yes
C2 N1 H1 127(2) . . ?
C5 N1 H1 125(2) . . ?
N3 C2 N1 112.7(2) . . yes
N3 C2 N6 126.6(2) . . yes
N1 C2 N6 120.6(2) . . yes
C2 N3 C4 104.1(2) . . yes
C5 C4 N3 110.7(2) . . yes
C5 C4 C7 130.9(2) . . yes
N3 C4 C7 118.3(2) . . yes
C4 C5 N1 104.4(2) . . yes
C4 C5 C12 135.7(2) . . yes
N1 C5 C12 119.9(2) . . yes
C2 N6 H6A 113(2) . . ?
C2 N6 H6B 112(3) . . ?
H6A N6 H6B 118(3) . . ?
O8 C7 O9 122.7(2) . . yes
O8 C7 C4 124.6(2) . . yes
O9 C7 C4 112.6(2) . . yes
C7 O9 C10 117.4(2) . . yes
O9 C10 C11 111.7(3) . . yes
O9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
O9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C12 C13 116.4(2) . . yes
C5 C12 H12A 108.2 . . ?
C13 C12 H12A 108.2 . . ?
C5 C12 H12B 108.2 . . ?
C13 C12 H12B 108.2 . . ?
H12A C12 H12B 107.3 . . ?
C16 C13 C14 109.5(3) . . yes
C16 C13 C15 109.5(3) . . yes
C14 C13 C15 108.9(3) . . yes
C16 C13 C12 111.5(2) . . yes
C14 C13 C12 110.7(2) . . yes
C15 C13 C12 106.6(3) . . yes
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C5 N1 C2 N3 0.1(3) . . . . yes
C5 N1 C2 N6 -177.4(2) . . . . yes
N1 C2 N3 C4 -0.3(3) . . . . yes
N6 C2 N3 C4 177.0(3) . . . . yes
C2 N3 C4 C5 0.3(3) . . . . yes
C2 N3 C4 C7 -176.6(2) . . . . yes
N3 C4 C5 N1 -0.3(3) . . . . yes
C7 C4 C5 N1 176.2(3) . . . . yes
N3 C4 C5 C12 -179.6(3) . . . . yes
C7 C4 C5 C12 -3.2(5) . . . . yes
C2 N1 C5 C4 0.1(3) . . . . yes
C2 N1 C5 C12 179.6(2) . . . . yes
C5 C4 C7 O8 -175.8(3) . . . . yes
N3 C4 C7 O8 0.5(4) . . . . yes
C5 C4 C7 O9 5.3(4) . . . . yes
N3 C4 C7 O9 -178.4(2) . . . . yes
O8 C7 O9 C10 0.9(4) . . . . yes
C4 C7 O9 C10 179.9(2) . . . . yes
C7 O9 C10 C11 -84.0(3) . . . . yes
C4 C5 C12 C13 -97.0(4) . . . . yes
N1 C5 C12 C13 83.7(3) . . . . yes
C5 C12 C13 C16 66.0(3) . . . . yes
C5 C12 C13 C14 -56.2(3) . . . . yes
C5 C12 C13 C15 -174.5(3) . . . . yes

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 N3 0.98(4) 1.84(4) 2.824(3) 177(3) 8_655 yes
N6 H6A O8 0.95(4) 2.05(4) 2.963(3) 161(3) 4_466 yes
N6 H6B O8 0.85(4) 2.26(4) 3.061(3) 158(3) 8_655 yes

_refine_diff_density_max         0.570
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.068

_diffrn_source_type              'Incoatec microfocus 3.0 (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_collimation    'focussed source'

_diffrn_orient_matrix_type       'Bruker AXS Inc. convention APEX3'
_diffrn_orient_matrix_UB_11      -8.0403566e-002
_diffrn_orient_matrix_UB_12      -1.5682977e-002
_diffrn_orient_matrix_UB_13      2.8434682e-003
_diffrn_orient_matrix_UB_21      -2.9430024e-002
_diffrn_orient_matrix_UB_22      3.9546628e-002
_diffrn_orient_matrix_UB_23      2.6212515e-002
_diffrn_orient_matrix_UB_31      -9.8942267e-003
_diffrn_orient_matrix_UB_32      9.8147076e-003
_diffrn_orient_matrix_UB_33      -1.0107511e-001

_diffrn_measurement_details      
;
Collection strategy, angles in degrees, time in seconds
Scan_type dx 2theta omega phi chi exposure_time width scan_range direction
#=============================================================================
Fast    80.000    0.000    0.000    0.000  54.781   1.000   1.000
Omega   80.000   68.684 -136.442  162.000  54.740   9.800   0.500 230.500 pos
Omega   80.000  112.960  -92.166    0.000  54.740  24.000   0.500 230.500 pos
Omega   80.000  112.960  -92.166  -72.000  54.740  24.000   0.500 230.500 pos
Omega   80.000   68.684 -136.442  108.000  54.740   9.800   0.500 230.500 pos
Omega   80.000  112.960  -92.166   72.000  54.740  24.000   0.500 230.500 pos
Omega   80.000  -27.880 -233.007  -80.000  54.740   6.000   0.500 230.500 pos
Omega   80.000  112.960  -92.166 -168.000  54.740  24.000   0.500 230.500 pos
Omega   80.000   82.960 -122.166    0.000  54.740  12.900   0.500 230.500 pos
Omega   80.000  112.960  -92.166  144.000  54.740  24.000   0.500 230.500 pos
Phi     80.000   97.960 -107.415    0.000  54.781  17.600   0.500 360.000 pos
Omega   80.000   97.960 -107.166  180.000  54.740  17.600   0.500 230.500 pos
Omega   80.000   82.960 -122.166   90.000  54.740  12.900   0.500 230.500 pos
Omega   80.000  112.960  -92.166  168.000  54.740  24.000   0.500 230.500 pos
Omega   80.000  112.960  -92.166  120.000  54.740  24.000   0.500 230.500 pos
Omega   80.000  -38.684 -243.810  270.000  54.740   6.500   0.500 230.500 pos
Omega   80.000  112.960  -92.166   48.000  54.740  24.000   0.500 230.500 pos
Omega   80.000   68.684 -136.442  135.000  54.740   9.800   0.500 230.500 pos
Omega   80.000   68.684 -136.442   54.000  54.740   9.800   0.500 230.500 pos
Omega   80.000   97.960 -107.166   90.000  54.740  17.600   0.500 230.500 pos
Omega   80.000  112.960  -92.166 -144.000  54.740  24.000   0.500 230.500 pos
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 0 0.0550
0 -1 0 0.0090
0 1 0 0.0250
0 -1 1 0.4000
-1 0 -1 0.2030
2 1 0 0.0470
1 1 -1 0.1700
-1 -2 0 0.0370
1 -2 0 0.0340
-1 1 2 0.3980
1 -2 1 0.2870

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol and water'
