# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_380k
_database_code_depnum_ccdc_archive 'CCDC 2313630'
loop_
_audit_author_name
_audit_author_address
'Jiantao Meng'
;China Pharmaceutical University
China
;
_audit_update_record             
;
2023-12-12 deposited with the CCDC.	2024-03-20 downloaded from the CCDC.
;
_audit_creation_date             2022-07-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
2-amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-1H-purin-6-one
_chemical_name_systematic        penciclovir
_chemical_formula_moiety         'C10 H15 N5 O3'
_chemical_formula_sum            'C10 H15 N5 O3'
_chemical_formula_weight         253.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.8542(16)
_cell_length_b                   10.8829(13)
_cell_length_c                   8.9354(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.888(5)
_cell_angle_gamma                90
_cell_volume                     1135.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1960
_cell_measurement_temperature    380
_cell_measurement_theta_max      25.252
_cell_measurement_theta_min      2.558
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1705 before and 0.0563 after correction. The Ratio of minimum to maximum transmission is 0.8606. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8424
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.392
_diffrn_reflns_theta_min         2.558
_diffrn_ambient_temperature      380.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1409
_reflns_number_total             2312
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0560
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0652P)²+0.3836P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1556
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B), C10(H10A,H10B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5)
2.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O2(H2A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.06507(15) 0.72842(17) 0.1864(2) 0.0576(6) Uani 1 1 d . . . . .
N5 N 0.22122(15) 0.59794(19) 0.5631(2) 0.0413(5) Uani 1 1 d . . . . .
N3 N 0.19650(15) 0.81846(19) 0.5378(2) 0.0408(5) Uani 1 1 d . . . . .
N2 N 0.04802(15) 0.86626(19) 0.3327(2) 0.0430(6) Uani 1 1 d . . . . .
H2 H 0.011552 0.924386 0.279901 0.052 Uiso 1 1 calc R . . . .
N4 N 0.08687(16) 0.53345(19) 0.3720(2) 0.0457(6) Uani 1 1 d . . . . .
O3 O 0.72815(16) 0.7143(2) 0.8094(3) 0.0819(8) Uani 1 1 d . . . . .
H3 H 0.783494 0.732154 0.769870 0.123 Uiso 1 1 calc GR . . . .
O2 O 0.6225(2) 0.4422(2) 0.7427(3) 0.0846(8) Uani 1 1 d . . . . .
H2A H 0.667819 0.395728 0.794487 0.127 Uiso 1 1 calc GR . . . .
N1 N 0.14498(17) 1.0191(2) 0.4788(3) 0.0575(7) Uani 1 1 d . . . . .
H1A H 0.196275 1.044361 0.552312 0.069 Uiso 1 1 calc R . . . .
H1B H 0.102535 1.071263 0.422758 0.069 Uiso 1 1 calc R . . . .
C4 C 0.17074(18) 0.7014(2) 0.4957(3) 0.0380(6) Uani 1 1 d . . . . .
C1 C 0.13130(19) 0.8994(2) 0.4518(3) 0.0409(6) Uani 1 1 d . . . . .
C2 C 0.01792(19) 0.7472(2) 0.2906(3) 0.0416(6) Uani 1 1 d . . . . .
C7 C 0.43036(19) 0.6269(3) 0.6315(3) 0.0485(7) Uani 1 1 d . . . . .
H7A H 0.419810 0.703829 0.576146 0.058 Uiso 1 1 calc R . . . .
H7B H 0.446150 0.563785 0.561270 0.058 Uiso 1 1 calc R . . . .
C3 C 0.08789(19) 0.6599(2) 0.3783(3) 0.0394(6) Uani 1 1 d . . . . .
C5 C 0.16781(19) 0.5003(3) 0.4837(3) 0.0467(7) Uani 1 1 d . . . . .
H5 H 0.187062 0.418797 0.506688 0.056 Uiso 1 1 calc R . . . .
C6 C 0.31986(19) 0.5949(3) 0.6868(3) 0.0468(7) Uani 1 1 d . . . . .
H6A H 0.326545 0.513401 0.731523 0.056 Uiso 1 1 calc R . . . .
H6B H 0.307612 0.652700 0.765026 0.056 Uiso 1 1 calc R . . . .
C8 C 0.53393(19) 0.6389(3) 0.7584(3) 0.0482(7) Uani 1 1 d . . . . .
H8 H 0.512498 0.694477 0.835166 0.058 Uiso 1 1 calc R . . . .
C10 C 0.5708(2) 0.5172(3) 0.8372(3) 0.0627(9) Uani 1 1 d . . . . .
H10A H 0.624141 0.532962 0.930307 0.075 Uiso 1 1 calc R . . . .
H10B H 0.504453 0.475759 0.863443 0.075 Uiso 1 1 calc R . . . .
C9 C 0.6300(2) 0.6990(3) 0.6946(4) 0.0610(9) Uani 1 1 d . . . . .
H9A H 0.649730 0.648610 0.613355 0.073 Uiso 1 1 calc R . . . .
H9B H 0.604939 0.778482 0.652408 0.073 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.250(3) . ?
N5 C4 1.366(3) . ?
N5 C5 1.371(3) . ?
N5 C6 1.465(3) . ?
N3 C4 1.349(3) . ?
N3 C1 1.327(3) . ?
N2 C1 1.370(3) . ?
N2 C2 1.379(3) . ?
N4 C3 1.378(3) . ?
N4 C5 1.311(3) . ?
O3 C9 1.423(3) . ?
O2 C10 1.390(4) . ?
N1 C1 1.329(3) . ?
C4 C3 1.384(3) . ?
C2 C3 1.407(3) . ?
C7 C6 1.518(4) . ?
C7 C8 1.527(3) . ?
C8 C10 1.528(4) . ?
C8 C9 1.507(4) . ?

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 N5 C5 106.38(19) . . ?
C4 N5 C6 125.8(2) . . ?
C5 N5 C6 127.6(2) . . ?
C1 N3 C4 112.6(2) . . ?
C1 N2 C2 125.3(2) . . ?
C5 N4 C3 104.1(2) . . ?
N5 C4 C3 105.4(2) . . ?
N3 C4 N5 126.5(2) . . ?
N3 C4 C3 128.1(2) . . ?
N3 C1 N2 123.1(2) . . ?
N3 C1 N1 120.3(2) . . ?
N1 C1 N2 116.6(2) . . ?
O1 C2 N2 119.4(2) . . ?
O1 C2 C3 128.1(2) . . ?
N2 C2 C3 112.5(2) . . ?
C6 C7 C8 114.0(2) . . ?
N4 C3 C4 110.9(2) . . ?
N4 C3 C2 130.7(2) . . ?
C4 C3 C2 118.4(2) . . ?
N4 C5 N5 113.2(2) . . ?
N5 C6 C7 111.8(2) . . ?
C7 C8 C10 113.4(2) . . ?
C9 C8 C7 108.7(2) . . ?
C9 C8 C10 112.0(2) . . ?
O2 C10 C8 110.5(2) . . ?
O3 C9 C8 110.9(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol-H2O mixed solvent'
####################################################################### 
# 
# 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_2022710_0m
_database_code_depnum_ccdc_archive 'CCDC 2313632'
loop_
_audit_author_name
_audit_author_address
'Jiantao Meng'
;China Pharmaceutical University
China
;
_audit_update_record             
;
2023-12-12 deposited with the CCDC.	2024-03-20 downloaded from the CCDC.
;
_audit_creation_date             2022-07-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
2-amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-1H-purin-6-one
_chemical_name_systematic        penciclovir
_chemical_formula_moiety         'C10 H15 N5 O3'
_chemical_formula_sum            'C10 H15 N5 O3'
_chemical_formula_weight         253.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.093(4)
_cell_length_b                   10.918(4)
_cell_length_c                   11.805(4)
_cell_angle_alpha                87.335(12)
_cell_angle_beta                 80.598(13)
_cell_angle_gamma                86.279(15)
_cell_volume                     1153.1(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3119
_cell_measurement_temperature    400
_cell_measurement_theta_max      25.83
_cell_measurement_theta_min      3.12
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1526 before and 0.0573 after correction. The Ratio of minimum to maximum transmission is 0.8721. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0701
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13021
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.451
_diffrn_reflns_theta_min         1.870
_diffrn_ambient_temperature      400
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2826
_reflns_number_total             4689
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4689
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1243
_refine_ls_R_factor_gt           0.0729
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0759P)²+0.5902P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1664
_refine_ls_wR_factor_ref         0.1971
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Rigid bond restraints
 C19, C18
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
C19 \\sim C18: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01
4.a Ternary CH refined with riding coordinates:
 C18(H18), C8(H8)
4.b Secondary CH2 refined with riding coordinates:
 C17(H17a,H17b), C7(H7a,H7b), C6(H6a,H6b), C16(H16a,H16b), C10(H10a,H10b),
 C19(H19a,H19b), C9(H9a,H9b), C20(H20a,H20b)
4.c Aromatic/amide H refined with riding coordinates:
 N007(H007), N008(H008), C5(H5), C15(H15)
4.d X=CH2 refined with riding coordinates:
 N00A(H00a,H00b), N00B(H00c,H00d)
4.e Idealised tetrahedral OH refined as rotating group:
 O5(H5a), O6(H6), O2(H2), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3284(3) 0.7472(2) 0.43698(18) 0.0638(7) Uani 1 1 d . . . . .
O4 O 0.1963(3) 0.2515(2) 0.56180(18) 0.0654(7) Uani 1 1 d . . . . .
N003 N 0.5356(3) 0.3321(2) 0.2949(2) 0.0479(7) Uani 1 1 d . . . . .
N004 N -0.0214(3) 0.8450(2) 0.6939(2) 0.0472(6) Uani 1 1 d . . . . .
N005 N -0.0505(3) 0.6248(2) 0.7151(2) 0.0489(7) Uani 1 1 d . . . . .
N006 N 0.5582(3) 0.1107(2) 0.27290(19) 0.0470(6) Uani 1 1 d . . . . .
N007 N 0.1845(3) 0.8879(2) 0.5487(2) 0.0489(7) Uani 1 1 d . . . . .
H007 H 0.238430 0.944291 0.513798 0.059 Uiso 1 1 calc R . . . .
N008 N 0.3385(3) 0.3856(2) 0.4455(2) 0.0499(7) Uani 1 1 d . . . . .
H008 H 0.288014 0.445320 0.481513 0.060 Uiso 1 1 calc R . . . .
N009 N 0.3742(3) 0.0520(2) 0.4108(2) 0.0537(7) Uani 1 1 d . . . . .
N00A N 0.0427(3) 1.0438(3) 0.6459(2) 0.0664(9) Uani 1 1 d . . . . .
H00A H -0.029491 1.070910 0.696588 0.080 Uiso 1 1 calc R . . . .
H00B H 0.099867 1.094373 0.604872 0.080 Uiso 1 1 calc R . . . .
N00B N 0.4802(4) 0.5332(3) 0.3454(2) 0.0677(9) Uani 1 1 d . . . . .
H00C H 0.550897 0.556527 0.292821 0.081 Uiso 1 1 calc R . . . .
H00D H 0.426798 0.586478 0.388173 0.081 Uiso 1 1 calc R . . . .
N00C N 0.1367(3) 0.5569(2) 0.5816(2) 0.0550(7) Uani 1 1 d . . . . .
O5 O 0.8169(3) 0.2280(3) -0.2335(2) 0.0985(10) Uani 1 1 d . . . . .
H5A H 0.780819 0.231936 -0.292934 0.148 Uiso 1 1 calc GR . . . .
O6 O 0.7432(4) -0.0442(3) -0.1264(3) 0.1029(10) Uani 1 1 d . . . . .
H6 H 0.792664 -0.075285 -0.183398 0.154 Uiso 1 1 calc GR . . . .
O2 O -0.3020(3) 0.7170(3) 1.2234(2) 0.0912(10) Uani 1 1 d . . . . .
H2 H -0.266300 0.731522 1.280455 0.137 Uiso 1 1 calc GR . . . .
O3 O -0.2522(4) 0.4489(3) 1.1011(4) 0.1120(12) Uani 1 1 d . . . . .
H3 H -0.306874 0.408654 1.148896 0.168 Uiso 1 1 calc GR . . . .
C14 C 0.4937(3) 0.2164(3) 0.3226(2) 0.0440(7) Uani 1 1 d . . . . .
C4 C 0.0185(3) 0.7268(3) 0.6669(2) 0.0451(7) Uani 1 1 d . . . . .
C18 C 0.7568(4) 0.1477(3) -0.0382(2) 0.0555(8) Uani 1 1 d . U . . .
H18 H 0.831699 0.196957 -0.013995 0.067 Uiso 1 1 calc R . . . .
C2 C 0.2232(4) 0.7685(3) 0.5181(2) 0.0468(7) Uani 1 1 d . . . . .
C3 C 0.1335(3) 0.6832(3) 0.5848(2) 0.0450(7) Uani 1 1 d . . . . .
C13 C 0.3807(4) 0.1782(3) 0.4075(2) 0.0463(7) Uani 1 1 d . . . . .
C12 C 0.2968(4) 0.2676(3) 0.4782(2) 0.0484(8) Uani 1 1 d . . . . .
C17 C 0.6285(4) 0.1402(3) 0.0624(2) 0.0528(8) Uani 1 1 d . . . . .
H17A H 0.573945 0.219564 0.069636 0.063 Uiso 1 1 calc R . . . .
H17B H 0.560386 0.080963 0.046133 0.063 Uiso 1 1 calc R . . . .
C1 C 0.0660(4) 0.9241(3) 0.6311(2) 0.0469(7) Uani 1 1 d . . . . .
C7 C -0.1208(3) 0.6416(3) 0.9256(2) 0.0516(8) Uani 1 1 d . . . . .
H7A H -0.061925 0.713438 0.917553 0.062 Uiso 1 1 calc R . . . .
H7B H -0.056100 0.571168 0.942183 0.062 Uiso 1 1 calc R . . . .
C6 C -0.1733(4) 0.6235(3) 0.8124(2) 0.0517(8) Uani 1 1 d . . . . .
H6A H -0.219965 0.545710 0.816250 0.062 Uiso 1 1 calc R . . . .
H6B H -0.247905 0.688244 0.800055 0.062 Uiso 1 1 calc R . . . .
C8 C -0.2472(4) 0.6579(3) 1.0271(2) 0.0529(8) Uani 1 1 d . . . . .
H8 H -0.315411 0.725137 1.005911 0.063 Uiso 1 1 calc R . . . .
C16 C 0.6806(4) 0.1033(3) 0.1755(2) 0.0544(8) Uani 1 1 d . . . . .
H16A H 0.724384 0.019921 0.171643 0.065 Uiso 1 1 calc R . . . .
H16B H 0.757287 0.156754 0.187669 0.065 Uiso 1 1 calc R . . . .
C5 C 0.0261(4) 0.5263(3) 0.6602(3) 0.0550(8) Uani 1 1 d . . . . .
H5 H 0.001440 0.445493 0.677423 0.066 Uiso 1 1 calc R . . . .
C15 C 0.4813(4) 0.0163(3) 0.3293(3) 0.0539(8) Uani 1 1 d . . . . .
H15 H 0.503236 -0.065543 0.311320 0.065 Uiso 1 1 calc R . . . .
C11 C 0.4535(4) 0.4148(3) 0.3606(2) 0.0483(8) Uani 1 1 d . . . . .
C10 C -0.3371(4) 0.5456(4) 1.0554(3) 0.0775(12) Uani 1 1 d . . . . .
H10A H -0.425560 0.566158 1.110618 0.093 Uiso 1 1 calc R . . . .
H10B H -0.369175 0.519574 0.986317 0.093 Uiso 1 1 calc R . . . .
C19 C 0.8348(5) 0.0219(4) -0.0715(3) 0.0716(10) Uani 1 1 d . U . . .
H19A H 0.928457 0.033766 -0.122231 0.086 Uiso 1 1 calc R . . . .
H19B H 0.856529 -0.023656 -0.003116 0.086 Uiso 1 1 calc R . . . .
C9 C -0.1850(4) 0.6970(4) 1.1293(3) 0.0649(10) Uani 1 1 d . . . . .
H9A H -0.113489 0.633853 1.150754 0.078 Uiso 1 1 calc R . . . .
H9B H -0.133387 0.771978 1.109616 0.078 Uiso 1 1 calc R . . . .
C20 C 0.7012(5) 0.2169(4) -0.1377(3) 0.0749(11) Uani 1 1 d . . . . .
H20A H 0.620524 0.174330 -0.159831 0.090 Uiso 1 1 calc R . . . .
H20B H 0.662012 0.298198 -0.114131 0.090 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.256(3) . ?
O4 C12 1.245(3) . ?
N003 C14 1.354(4) . ?
N003 C11 1.328(4) . ?
N004 C4 1.356(4) . ?
N004 C1 1.328(4) . ?
N005 C4 1.368(4) . ?
N005 C6 1.465(4) . ?
N005 C5 1.372(4) . ?
N006 C14 1.372(4) . ?
N006 C16 1.465(4) . ?
N006 C15 1.368(4) . ?
N007 H007 0.8600 . ?
N007 C2 1.378(4) . ?
N007 C1 1.378(4) . ?
N008 H008 0.8600 . ?
N008 C12 1.387(4) . ?
N008 C11 1.368(4) . ?
N009 C13 1.381(4) . ?
N009 C15 1.305(4) . ?
N00A H00A 0.8600 . ?
N00A H00B 0.8600 . ?
N00A C1 1.326(4) . ?
N00B H00C 0.8600 . ?
N00B H00D 0.8600 . ?
N00B C11 1.329(4) . ?
N00C C3 1.380(4) . ?
N00C C5 1.301(4) . ?
O5 H5A 0.8200 . ?
O5 C20 1.420(4) . ?
O6 H6 0.8200 . ?
O6 C19 1.390(5) . ?
O2 H2 0.8200 . ?
O2 C9 1.421(4) . ?
O3 H3 0.8200 . ?
O3 C10 1.408(5) . ?
C14 C13 1.384(4) . ?
C4 C3 1.381(4) . ?
C18 H18 0.9800 . ?
C18 C17 1.526(4) . ?
C18 C19 1.542(5) . ?
C18 C20 1.506(5) . ?
C2 C3 1.404(4) . ?
C13 C12 1.415(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C16 1.518(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C6 1.516(4) . ?
C7 C8 1.528(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 H8 0.9800 . ?
C8 C10 1.511(5) . ?
C8 C9 1.504(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C5 H5 0.9300 . ?
C15 H15 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 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
C11 N003 C14 112.4(2) . . ?
C1 N004 C4 112.5(3) . . ?
C4 N005 C6 125.7(3) . . ?
C4 N005 C5 106.1(2) . . ?
C5 N005 C6 128.0(3) . . ?
C14 N006 C16 125.9(3) . . ?
C15 N006 C14 106.2(2) . . ?
C15 N006 C16 127.8(3) . . ?
C2 N007 H007 117.4 . . ?
C1 N007 H007 117.4 . . ?
C1 N007 C2 125.1(3) . . ?
C12 N008 H008 117.4 . . ?
C11 N008 H008 117.4 . . ?
C11 N008 C12 125.3(3) . . ?
C15 N009 C13 103.9(3) . . ?
H00A N00A H00B 120.0 . . ?
C1 N00A H00A 120.0 . . ?
C1 N00A H00B 120.0 . . ?
H00C N00B H00D 120.0 . . ?
C11 N00B H00C 120.0 . . ?
C11 N00B H00D 120.0 . . ?
C5 N00C C3 104.1(3) . . ?
C20 O5 H5A 109.5 . . ?
C19 O6 H6 109.5 . . ?
C9 O2 H2 109.5 . . ?
C10 O3 H3 109.5 . . ?
N003 C14 N006 126.7(3) . . ?
N003 C14 C13 128.2(3) . . ?
N006 C14 C13 105.1(3) . . ?
N004 C4 N005 126.5(3) . . ?
N004 C4 C3 128.2(3) . . ?
N005 C4 C3 105.4(3) . . ?
C17 C18 H18 107.0 . . ?
C17 C18 C19 113.7(3) . . ?
C19 C18 H18 107.0 . . ?
C20 C18 H18 107.0 . . ?
C20 C18 C17 109.0(3) . . ?
C20 C18 C19 112.7(3) . . ?
O1 C2 N007 119.4(3) . . ?
O1 C2 C3 127.8(3) . . ?
N007 C2 C3 112.8(3) . . ?
N00C C3 C4 110.9(3) . . ?
N00C C3 C2 130.6(3) . . ?
C4 C3 C2 118.5(3) . . ?
N009 C13 C14 111.0(3) . . ?
N009 C13 C12 130.4(3) . . ?
C14 C13 C12 118.5(3) . . ?
O4 C12 N008 119.6(3) . . ?
O4 C12 C13 128.3(3) . . ?
N008 C12 C13 112.1(3) . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C16 C17 C18 113.0(3) . . ?
C16 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
N004 C1 N007 122.9(3) . . ?
N00A C1 N004 120.6(3) . . ?
N00A C1 N007 116.5(3) . . ?
H7A C7 H7B 107.6 . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C6 C7 C8 114.0(3) . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
N005 C6 C7 112.2(3) . . ?
N005 C6 H6A 109.2 . . ?
N005 C6 H6B 109.2 . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C7 C8 H8 107.3 . . ?
C10 C8 C7 113.4(3) . . ?
C10 C8 H8 107.3 . . ?
C9 C8 C7 109.4(3) . . ?
C9 C8 H8 107.3 . . ?
C9 C8 C10 111.8(3) . . ?
N006 C16 C17 112.1(3) . . ?
N006 C16 H16A 109.2 . . ?
N006 C16 H16B 109.2 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
N005 C5 H5 123.2 . . ?
N00C C5 N005 113.5(3) . . ?
N00C C5 H5 123.2 . . ?
N006 C15 H15 123.1 . . ?
N009 C15 N006 113.7(3) . . ?
N009 C15 H15 123.1 . . ?
N003 C11 N008 123.4(3) . . ?
N003 C11 N00B 120.3(3) . . ?
N00B C11 N008 116.3(3) . . ?
O3 C10 C8 111.0(3) . . ?
O3 C10 H10A 109.4 . . ?
O3 C10 H10B 109.4 . . ?
C8 C10 H10A 109.4 . . ?
C8 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O6 C19 C18 109.9(3) . . ?
O6 C19 H19A 109.7 . . ?
O6 C19 H19B 109.7 . . ?
C18 C19 H19A 109.7 . . ?
C18 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
O2 C9 C8 110.2(3) . . ?
O2 C9 H9A 109.6 . . ?
O2 C9 H9B 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
O5 C20 C18 111.4(3) . . ?
O5 C20 H20A 109.3 . . ?
O5 C20 H20B 109.3 . . ?
C18 C20 H20A 109.3 . . ?
C18 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Cooperative phase transition'
