# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_L-PhenylAlanine_H2O2
_audit_block_doi                 10.5517/ccdc.csd.cc27y8l2
_database_code_depnum_ccdc_archive 'CCDC 2083714'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D1CE00688F 2021
loop_
_audit_author_name
_audit_author_address
'Hiroyasu Tabe'
;Osaka City University
Japan
;
_audit_update_record             
;
2021-05-14 deposited with the CCDC.	2021-07-21 downloaded from the CCDC.
;

_audit_creation_date             2019-2-8
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
#-----------------------------------------------------------------------------#


_chemical_formula_moiety         'C9 H11 N O2, H2 O2, 0.5(H2 O)'
_chemical_formula_sum            'C9 H14 N O4.5'
_chemical_formula_weight         208.21

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   9.9671(3)
_cell_length_b                   7.2000(3)
_cell_length_c                   14.1385(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.803(3)
_cell_angle_gamma                90
_cell_volume                     1013.41(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4601
_cell_measurement_theta_min      3.4480
_cell_measurement_theta_max      29.8330

_exptl_crystal_size_max          0.4000
_exptl_crystal_size_mid          0.3600
_exptl_crystal_size_min          0.0200
_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colorless
_exptl_crystal_preparation       
'mounted on the CryoLoop with Palaton oil and placed in N2 stream at 150(2) K'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             444
_exptl_special_details           ?

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_min  0.78826
_exptl_absorpt_correction_T_max  1.00000

# EXPERIMENTAL DATA
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_method       'ω and φ'
_diffrn_measurement_device       'Mercury CCD (2x2 bin mode)'
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_device_details 'AFC7: Eulerian 3-circle'
_diffrn_detector_area_resol_mean 7.32
_diffrn_ambient_temperature      150(2)
_diffrn_source_power             10.0000
_diffrn_source_voltage           50.0000
_diffrn_source_current           200.0000

_diffrn_reflns_number            6166
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.1170
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_min         2.885
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.787
_diffrn_reflns_point_group_measured_fraction_full 0.805

_diffrn_measurement_details      
;
scan:
	Number of images: 600
	           Slice: -80.0000 - 100.000
	     Image width: 0.3000
	        Exp time: 24.0000
	   Rotation axis: Phi
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 0.0000
	             XTD: 54.1393
	          2theta: 25.8615
scan:
	Number of images: 200
	           Slice: -15.0000 - 45.0000
	     Image width: 0.3000
	        Exp time: 24.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 0.0000
	             XTD: 54.1393
	          2theta: 25.8615
scan:
	Number of images: 200
	           Slice: -15.0000 - 45.0000
	     Image width: 0.3000
	        Exp time: 24.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 90.0000
	             XTD: 54.1393
	          2theta: 25.8615
scan:
	Number of images: 200
	           Slice: -15.0000 - 45.0000
	     Image width: 0.3000
	        Exp time: 24.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 180.0000
	             XTD: 54.1393
	          2theta: 25.8615
scan:
	Number of images: 200
	           Slice: -15.0000 - 45.0000
	     Image width: 0.3000
	        Exp time: 24.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 270.0000
	             XTD: 54.1393
	          2theta: 25.8615
scan:
	Number of images: 195
	           Slice: -15.0000 - 43.5000
	     Image width: 0.3000
	        Exp time: 24.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 54.1393
	          2theta: 25.8615
scan:
	Number of images: 195
	           Slice: -15.0000 - 43.5000
	     Image width: 0.3000
	        Exp time: 24.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 54.1393
	          2theta: 25.8615
scan:
	Number of images: 195
	           Slice: -15.0000 - 43.5000
	     Image width: 0.3000
	        Exp time: 24.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 54.1393
	          2theta: 25.8615
scan:
	Number of images: 195
	           Slice: -15.0000 - 43.5000
	     Image width: 0.3000
	        Exp time: 24.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 54.1393
	          2theta: 25.8615

;


_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'


#--------- REFINEMENT INFORMATION ------------------
_reflns_number_total             1819
_reflns_number_gt                1738
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.461
_reflns_Friedel_fraction_max     0.540
_reflns_Friedel_fraction_full    0.575
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0877P)²+0.5312P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1819
_refine_ls_number_parameters     188
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1325
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_refine_ls_abs_structure_details 
;
 Flack x determined using 533 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.2(10)
_chemical_absolute_configuration rm

_refine_diff_density_max         0.355
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.063

_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.
;


#---------ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS-----------
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 0.2836(3) 0.1185(5) 0.31919(19) 0.0219(6) Uani 1 1 d . . . . .
C2 C 0.1500(3) 0.1427(5) 0.3423(2) 0.0266(7) Uani 1 1 d . . . . .
H2A H 0.084(4) 0.054(8) 0.317(3) 0.041(12) Uiso 1 1 d . . . . .
C3 C 0.1132(3) 0.2878(6) 0.3981(2) 0.0324(7) Uani 1 1 d . . . . .
H3A H 0.022(4) 0.300(8) 0.414(3) 0.036(11) Uiso 1 1 d . . . . .
C4 C 0.2074(4) 0.4128(6) 0.4337(3) 0.0378(9) Uani 1 1 d . . . . .
H4A H 0.188(5) 0.494(11) 0.474(4) 0.058(16) Uiso 1 1 d . . . . .
C5 C 0.3401(4) 0.3917(6) 0.4118(3) 0.0387(9) Uani 1 1 d . . . . .
H5A H 0.405(5) 0.479(10) 0.436(3) 0.053(14) Uiso 1 1 d . . . . .
C6 C 0.3769(3) 0.2450(6) 0.3549(2) 0.0307(7) Uani 1 1 d . . . . .
H6A H 0.472(4) 0.215(8) 0.341(3) 0.038(11) Uiso 1 1 d . . . . .
C7 C 0.3248(3) -0.0388(5) 0.2576(2) 0.0220(6) Uani 1 1 d . . . . .
H7A H 0.424(4) -0.052(7) 0.258(3) 0.026(9) Uiso 1 1 d . . . . .
H7B H 0.291(4) -0.156(7) 0.282(3) 0.019(8) Uiso 1 1 d . . . . .
C8 C 0.2747(2) -0.0232(4) 0.15389(19) 0.0163(5) Uani 1 1 d . . . . .
H8A H 0.316(4) -0.121(7) 0.117(3) 0.024(9) Uiso 1 1 d . . . . .
C9 C 0.1216(2) -0.0448(4) 0.13969(18) 0.0164(5) Uani 1 1 d . . . . .
O1 O 0.05557(18) 0.0931(3) 0.11370(15) 0.0212(5) Uani 1 1 d . . . . .
O2 O 0.07656(17) -0.2033(3) 0.15605(16) 0.0219(5) Uani 1 1 d . . . . .
N1 N 0.3153(2) 0.1558(4) 0.11296(18) 0.0178(5) Uani 1 1 d . . . . .
H1NA H 0.302(3) 0.144(6) 0.047(2) 0.012(8) Uiso 1 1 d . . . . .
H1NB H 0.269(4) 0.235(8) 0.133(3) 0.023(9) Uiso 1 1 d . . . . .
H1NC H 0.410(4) 0.192(8) 0.127(3) 0.044(13) Uiso 1 1 d . . . . .
O3 O 0.30043(18) 0.5448(3) 0.06643(14) 0.0209(5) Uani 1 1 d . . . . .
H3OA H 0.375(5) 0.562(8) 0.089(3) 0.036(11) Uiso 1 1 d . . . . .
O4 O 0.2404(2) 0.5124(3) 0.15726(15) 0.0242(5) Uani 1 1 d . . . . .
H4OA H 0.180(4) 0.616(9) 0.151(3) 0.042(12) Uiso 1 1 d . . . . .
O5 O 0.000000 0.4284(5) 0.000000 0.0237(7) Uani 1 2 d S T P . .
H5OA H 0.044(5) 0.357(10) 0.043(4) 0.047(13) Uiso 1 1 d . . . . .




#--------------MOLECULAR GEOMETRY------------------
_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
C1 C6 1.380(5) . ?
C1 C2 1.397(4) . ?
C1 C7 1.498(5) . ?
C2 C3 1.370(5) . ?
C2 H2A 0.97(5) . ?
C3 C4 1.378(6) . ?
C3 H3A 0.95(4) . ?
C4 C5 1.381(5) . ?
C4 H4A 0.84(7) . ?
C5 C6 1.388(6) . ?
C5 H5A 0.96(6) . ?
C6 H6A 1.01(4) . ?
C7 C8 1.530(4) . ?
C7 H7A 1.00(4) . ?
C7 H7B 0.98(5) . ?
C8 N1 1.477(4) . ?
C8 C9 1.537(3) . ?
C8 H8A 0.98(5) . ?
C9 O1 1.237(4) . ?
C9 O2 1.253(4) . ?
N1 H1NA 0.94(3) . ?
N1 H1NB 0.80(5) . ?
N1 H1NC 0.99(4) . ?
O3 O4 1.462(3) . ?
O3 H3OA 0.80(5) . ?
O4 H4OA 0.96(6) . ?
O5 H5OA 0.90(6) . ?
O5 H5OA 0.90(6) 2 ?

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
C6 C1 C2 117.7(3) . . ?
C6 C1 C7 120.8(3) . . ?
C2 C1 C7 121.5(3) . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 H2A 121(3) . . ?
C1 C2 H2A 118(3) . . ?
C2 C3 C4 120.7(3) . . ?
C2 C3 H3A 120(3) . . ?
C4 C3 H3A 119(3) . . ?
C3 C4 C5 119.3(4) . . ?
C3 C4 H4A 122(4) . . ?
C5 C4 H4A 118(4) . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5A 119(3) . . ?
C6 C5 H5A 121(3) . . ?
C1 C6 C5 121.4(3) . . ?
C1 C6 H6A 114(3) . . ?
C5 C6 H6A 124(3) . . ?
C1 C7 C8 114.6(3) . . ?
C1 C7 H7A 111(3) . . ?
C8 C7 H7A 107(2) . . ?
C1 C7 H7B 110(2) . . ?
C8 C7 H7B 107(2) . . ?
H7A C7 H7B 106(3) . . ?
N1 C8 C7 110.9(2) . . ?
N1 C8 C9 109.0(2) . . ?
C7 C8 C9 113.1(2) . . ?
N1 C8 H8A 107(3) . . ?
C7 C8 H8A 109(2) . . ?
C9 C8 H8A 107(2) . . ?
O1 C9 O2 126.6(2) . . ?
O1 C9 C8 117.9(2) . . ?
O2 C9 C8 115.5(2) . . ?
C8 N1 H1NA 106(3) . . ?
C8 N1 H1NB 108(3) . . ?
H1NA N1 H1NB 110(4) . . ?
C8 N1 H1NC 115(3) . . ?
H1NA N1 H1NC 108(3) . . ?
H1NB N1 H1NC 108(4) . . ?
O4 O3 H3OA 95(3) . . ?
O3 O4 H4OA 95(3) . . ?
H5OA O5 H5OA 110(8) . 2 ?

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
C6 C1 C2 C3 0.4(5) . . . . ?
C7 C1 C2 C3 -179.5(3) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C3 C4 C5 C6 -0.3(6) . . . . ?
C2 C1 C6 C5 -0.1(5) . . . . ?
C7 C1 C6 C5 179.8(3) . . . . ?
C4 C5 C6 C1 0.0(6) . . . . ?
C6 C1 C7 C8 -110.4(3) . . . . ?
C2 C1 C7 C8 69.5(4) . . . . ?
C1 C7 C8 N1 54.6(3) . . . . ?
C1 C7 C8 C9 -68.2(3) . . . . ?
N1 C8 C9 O1 -12.0(3) . . . . ?
C7 C8 C9 O1 111.9(3) . . . . ?
N1 C8 C9 O2 168.0(2) . . . . ?
C7 C8 C9 O2 -68.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C8 H8A O3 0.98(5) 2.51(5) 3.362(4) 145(3) 1_545 yes
C8 H8A O5 0.98(5) 2.56(4) 3.221(3) 125(3) 3_545 yes
N1 H1NA O3 0.94(3) 1.99(3) 2.849(3) 151(3) 4_545 yes
N1 H1NB O3 0.80(5) 2.44(5) 2.879(3) 116(4) . yes
N1 H1NB O4 0.80(5) 2.05(6) 2.755(4) 148(4) . yes
N1 H1NC O2 0.99(4) 1.85(5) 2.833(3) 171(5) 3 yes
O3 H3OA O1 0.80(5) 1.83(5) 2.621(3) 168(4) 3 yes
O4 H4OA O2 0.96(6) 1.66(6) 2.618(3) 173(4) 1_565 yes
O5 H5OA O1 0.90(6) 2.15(7) 2.938(3) 147(5) . yes



_chemical_name_systematic        L-Phe.H2O2.0.5H2O
_exptl_crystal_recrystallization_method 'Re-crystallisation from 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_DL-PhenylAlanine_H2O2-H2O
_audit_block_doi                 10.5517/ccdc.csd.cc27y8m3
_database_code_depnum_ccdc_archive 'CCDC 2083715'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D1CE00688F 2021
loop_
_audit_author_name
_audit_author_address
'Hiroyasu Tabe'
;Osaka City University
Japan
;
_audit_update_record             
;
2021-05-14 deposited with the CCDC.	2021-07-21 downloaded from the CCDC.
;

_audit_creation_date             2021-4-12
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
#-----------------------------------------------------------------------------#


_chemical_formula_moiety         'C9 H11 N O2, 0.9675(H2 O2), 0.0325(H2 O)'
_chemical_formula_sum            'C9 H13 N O3.9675'
_chemical_formula_weight         198.69

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -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, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   11.6333(3)
_cell_length_b                   5.98690(10)
_cell_length_c                   28.5029(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1985.15(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    12708
_cell_measurement_theta_min      2.8500
_cell_measurement_theta_max      27.5680

_exptl_crystal_size_max          0.2700
_exptl_crystal_size_mid          0.2100
_exptl_crystal_size_min          0.0300
_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colorless
_exptl_crystal_preparation       
'mounted on the CryoLoop with Palaton oil and placed in N2 stream at 200(2) K'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             846
_exptl_special_details           ?

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_min  0.77920
_exptl_absorpt_correction_T_max  1.00000

# EXPERIMENTAL DATA
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_method       'ω and φ'
_diffrn_measurement_device       'Mercury CCD (2x2 bin mode)'
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_device_details 'AFC7: Eulerian 3-circle'
_diffrn_detector_area_resol_mean 7.32
_diffrn_ambient_temperature      200(2)
_diffrn_source_power             13.7500
_diffrn_source_voltage           55.0000
_diffrn_source_current           250.0000


_diffrn_reflns_number            21898
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_min         2.859
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_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 0.929
_diffrn_reflns_point_group_measured_fraction_full 0.927

_diffrn_measurement_details      
;
scan:
	Number of images: 600
	           Slice: -80.0000 - 100.000
	     Image width: 0.3000
	        Exp time: 32.0000
	   Rotation axis: Phi
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 0.0000
	             XTD: 54.7609
	          2theta: 25.2041
scan:
	Number of images: 200
	           Slice: -15.0000 - 45.0000
	     Image width: 0.3000
	        Exp time: 32.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 0.0000
	             XTD: 54.7609
	          2theta: 25.2041
scan:
	Number of images: 200
	           Slice: -15.0000 - 45.0000
	     Image width: 0.3000
	        Exp time: 32.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 90.0000
	             XTD: 54.7609
	          2theta: 25.2041
scan:
	Number of images: 200
	           Slice: -15.0000 - 45.0000
	     Image width: 0.3000
	        Exp time: 32.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 180.0000
	             XTD: 54.7609
	          2theta: 25.2041
scan:
	Number of images: 200
	           Slice: -15.0000 - 45.0000
	     Image width: 0.3000
	        Exp time: 32.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 270.0000
	             XTD: 54.7609
	          2theta: 25.2041
scan:
	Number of images: 190
	           Slice: -15.0000 - 42.0000
	     Image width: 0.3000
	        Exp time: 32.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 54.7609
	          2theta: 25.2041
scan:
	Number of images: 190
	           Slice: -15.0000 - 42.0000
	     Image width: 0.3000
	        Exp time: 32.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 54.7609
	          2theta: 25.2041
scan:
	Number of images: 190
	           Slice: -15.0000 - 42.0000
	     Image width: 0.3000
	        Exp time: 32.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 54.7609
	          2theta: 25.2041
scan:
	Number of images: 190
	           Slice: -15.0000 - 42.0000
	     Image width: 0.3000
	        Exp time: 32.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 54.7609
	          2theta: 25.2041

;


_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'


#--------- REFINEMENT INFORMATION ------------------
_reflns_number_total             4224
_reflns_number_gt                3761
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0506P)²+0.1769P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4224
_refine_ls_number_parameters     368
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0879
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

_reflns_Friedel_coverage         0.821
_reflns_Friedel_fraction_max     0.855
_reflns_Friedel_fraction_full    0.852

_refine_ls_abs_structure_details 
;
 Flack x determined using 1493 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(5)
_chemical_absolute_configuration ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.035

_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.
;


#---------ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS-----------
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 0.4669(3) 0.8412(4) 0.16468(9) 0.0294(6) Uani 1 1 d . . . . .
C2 C 0.3990(3) 0.6487(4) 0.16506(11) 0.0375(7) Uani 1 1 d . . . . .
H2A H 0.422(3) 0.523(6) 0.1451(12) 0.047(9) Uiso 1 1 d . . . . .
C3 C 0.2997(3) 0.6363(5) 0.19212(12) 0.0435(7) Uani 1 1 d . . . . .
H3A H 0.252(3) 0.498(6) 0.1910(14) 0.053(10) Uiso 1 1 d . . . . .
C4 C 0.2677(3) 0.8158(5) 0.21993(11) 0.0422(7) Uani 1 1 d . . . . .
H4A H 0.198(4) 0.811(6) 0.2410(14) 0.060(11) Uiso 1 1 d . . . . .
C5 C 0.3345(3) 1.0063(5) 0.22010(11) 0.0429(7) Uani 1 1 d . . . . .
H5A H 0.311(3) 1.129(6) 0.2368(14) 0.052(10) Uiso 1 1 d . . . . .
C6 C 0.4330(3) 1.0191(4) 0.19257(11) 0.0368(7) Uani 1 1 d . . . . .
H6A H 0.480(3) 1.140(5) 0.1927(12) 0.036(8) Uiso 1 1 d . . . . .
C7 C 0.5741(2) 0.8568(4) 0.13505(11) 0.0297(6) Uani 1 1 d . . . . .
H7A H 0.610(3) 0.717(5) 0.1329(12) 0.039(8) Uiso 1 1 d . . . . .
H7B H 0.625(3) 0.971(6) 0.1492(12) 0.039(8) Uiso 1 1 d . . . . .
C8 C 0.5527(2) 0.9232(3) 0.08362(10) 0.0233(5) Uani 1 1 d . . . . .
H8A H 0.625(2) 0.938(4) 0.0683(10) 0.018(6) Uiso 1 1 d . . . . .
N1 N 0.48756(19) 0.7479(3) 0.05786(8) 0.0243(5) Uani 1 1 d . . . . .
H1NA H 0.415(3) 0.755(5) 0.0652(13) 0.035(8) Uiso 1 1 d . . . . .
H1NB H 0.496(2) 0.769(4) 0.0248(11) 0.022(7) Uiso 1 1 d . . . . .
H1NC H 0.511(4) 0.619(7) 0.0687(16) 0.060(11) Uiso 1 1 d . . . . .
C9 C 0.4852(2) 1.1439(3) 0.07969(10) 0.0242(5) Uani 1 1 d . . . . .
O1 O 0.38087(15) 1.1345(3) 0.07192(8) 0.0351(5) Uani 1 1 d . . . . .
O2 O 0.54412(15) 1.3194(2) 0.08642(7) 0.0320(4) Uani 1 1 d . . . . .
C10 C 0.2054(2) 0.6171(4) 0.34532(10) 0.0292(6) Uani 1 1 d . . . . .
C11 C 0.1262(3) 0.7921(4) 0.34193(10) 0.0337(6) Uani 1 1 d . . . . .
H11A H 0.145(3) 0.928(5) 0.3584(12) 0.040(8) Uiso 1 1 d . . . . .
C12 C 0.0301(3) 0.7731(5) 0.31350(11) 0.0416(7) Uani 1 1 d . . . . .
H12A H -0.023(3) 0.892(6) 0.3123(13) 0.049(9) Uiso 1 1 d . . . . .
C13 C 0.0103(3) 0.5794(5) 0.28796(12) 0.0434(7) Uani 1 1 d . . . . .
H13A H -0.054(3) 0.567(5) 0.2669(12) 0.045(9) Uiso 1 1 d . . . . .
C14 C 0.0884(3) 0.4042(5) 0.29078(12) 0.0440(7) Uani 1 1 d . . . . .
H14A H 0.068(3) 0.273(6) 0.2733(13) 0.049(10) Uiso 1 1 d . . . . .
C15 C 0.1845(3) 0.4227(4) 0.31920(11) 0.0366(6) Uani 1 1 d . . . . .
H15A H 0.232(3) 0.301(6) 0.3223(14) 0.051(10) Uiso 1 1 d . . . . .
C16 C 0.3085(2) 0.6296(4) 0.37747(10) 0.0287(6) Uani 1 1 d . . . . .
H16A H 0.347(3) 0.782(5) 0.3742(12) 0.042(9) Uiso 1 1 d . . . . .
H16B H 0.370(3) 0.522(6) 0.3673(12) 0.042(9) Uiso 1 1 d . . . . .
C17 C 0.2829(2) 0.5680(3) 0.42859(10) 0.0231(5) Uani 1 1 d . . . . .
H17A H 0.354(2) 0.546(4) 0.4468(9) 0.016(6) Uiso 1 1 d . . . . .
N2 N 0.21585(19) 0.7473(3) 0.45284(9) 0.0245(4) Uani 1 1 d . . . . .
H2NA H 0.141(3) 0.726(5) 0.4464(11) 0.031(8) Uiso 1 1 d . . . . .
H2NB H 0.228(3) 0.736(4) 0.4861(12) 0.029(7) Uiso 1 1 d . . . . .
H2NC H 0.240(3) 0.889(5) 0.4429(12) 0.031(8) Uiso 1 1 d . . . . .
C18 C 0.2135(2) 0.3486(3) 0.43193(10) 0.0260(5) Uani 1 1 d . . . . .
O3 O 0.10954(17) 0.3602(3) 0.44049(8) 0.0354(5) Uani 1 1 d . . . . .
O4 O 0.27126(16) 0.1730(2) 0.42377(7) 0.0324(5) Uani 1 1 d . . . . .
O5 O 0.23163(17) 0.4196(3) 0.03479(8) 0.0332(5) Uani 1 1 d . . . . .
H5O H 0.291(3) 0.356(5) 0.0511(12) 0.037(8) Uiso 1 1 d . . . . .
O6 O 0.24980(18) 0.6462(3) 0.05196(8) 0.0348(5) Uani 1 1 d . . . . .
H6O H 0.171(4) 0.670(7) 0.0665(18) 0.073(12) Uiso 1 1 d . . . . .
O7 O 0.46113(18) -0.0752(3) 0.47743(8) 0.0335(7) Uani 0.935(7) 1 d . . P A 1
H7O H 0.513(4) -0.147(7) 0.4638(16) 0.050 Uiso 0.935(7) 1 d . U P A 1
O8 O 0.4779(2) 0.1470(3) 0.45817(12) 0.0355(8) Uani 0.935(7) 1 d . . P A 1
H8O H 0.414(3) 0.155(6) 0.4433(16) 0.053 Uiso 0.935(7) 1 d . U P A 1
O9 O 0.484(2) 0.123(4) 0.4282(12) 0.018(7) Uani 0.065(7) 1 d D . P A 2
H9OA H 0.414(3) 0.155(6) 0.4433(16) 0.028 Uiso 0.065(7) 1 d D U P A 2
H9OB H 0.535(8) 0.19(7) 0.449(9) 0.028 Uiso 0.065(7) 1 d D U P A 2




#--------------MOLECULAR GEOMETRY------------------
_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
C1 C6 1.386(4) . ?
C1 C2 1.397(4) . ?
C1 C7 1.509(4) . ?
C2 C3 1.391(5) . ?
C2 H2A 0.98(4) . ?
C3 C4 1.386(5) . ?
C3 H3A 1.00(4) . ?
C4 C5 1.380(5) . ?
C4 H4A 1.01(4) . ?
C5 C6 1.391(5) . ?
C5 H5A 0.92(4) . ?
C6 H6A 0.91(3) . ?
C7 C8 1.539(4) . ?
C7 H7A 0.94(3) . ?
C7 H7B 0.99(3) . ?
C8 N1 1.488(3) . ?
C8 C9 1.542(3) . ?
C8 H8A 0.96(3) . ?
N1 H1NA 0.87(4) . ?
N1 H1NB 0.95(3) . ?
N1 H1NC 0.87(4) . ?
C9 O1 1.235(3) . ?
C9 O2 1.269(3) . ?
C10 C11 1.399(4) . ?
C10 C15 1.403(4) . ?
C10 C16 1.510(4) . ?
C11 C12 1.386(4) . ?
C11 H11A 0.97(3) . ?
C12 C13 1.389(5) . ?
C12 H12A 0.94(4) . ?
C13 C14 1.390(5) . ?
C13 H13A 0.96(4) . ?
C14 C15 1.386(5) . ?
C14 H14A 0.96(4) . ?
C15 H15A 0.92(4) . ?
C16 C17 1.532(4) . ?
C16 H16A 1.02(3) . ?
C16 H16B 1.01(3) . ?
C17 N2 1.496(3) . ?
C17 C18 1.544(3) . ?
C17 H17A 0.99(3) . ?
N2 H2NA 0.90(3) . ?
N2 H2NB 0.96(3) . ?
N2 H2NC 0.94(3) . ?
C18 O3 1.236(3) . ?
C18 O4 1.269(3) . ?
O5 O6 1.458(2) . ?
O5 H5O 0.92(4) . ?
O6 H6O 1.02(5) . ?
O7 O8 1.452(3) . ?
O7 H7O 0.84(5) . ?
O8 H8O 0.85(4) . ?
O9 H9OA 0.94(3) . ?
O9 H9OB 0.94(3) . ?

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
C6 C1 C2 117.9(3) . . ?
C6 C1 C7 120.6(2) . . ?
C2 C1 C7 121.5(2) . . ?
C3 C2 C1 121.2(3) . . ?
C3 C2 H2A 120(2) . . ?
C1 C2 H2A 118(2) . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3A 121(2) . . ?
C2 C3 H3A 119(2) . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4A 118(2) . . ?
C3 C4 H4A 122(2) . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5A 120(2) . . ?
C6 C5 H5A 119(2) . . ?
C1 C6 C5 121.1(3) . . ?
C1 C6 H6A 117(2) . . ?
C5 C6 H6A 122(2) . . ?
C1 C7 C8 114.5(2) . . ?
C1 C7 H7A 110.5(19) . . ?
C8 C7 H7A 104(2) . . ?
C1 C7 H7B 108.1(19) . . ?
C8 C7 H7B 108(2) . . ?
H7A C7 H7B 112(3) . . ?
N1 C8 C7 111.73(19) . . ?
N1 C8 C9 108.02(19) . . ?
C7 C8 C9 111.9(2) . . ?
N1 C8 H8A 106.9(16) . . ?
C7 C8 H8A 108.3(16) . . ?
C9 C8 H8A 109.8(14) . . ?
C8 N1 H1NA 110(2) . . ?
C8 N1 H1NB 110.0(16) . . ?
H1NA N1 H1NB 109(3) . . ?
C8 N1 H1NC 107(3) . . ?
H1NA N1 H1NC 105(3) . . ?
H1NB N1 H1NC 116(3) . . ?
O1 C9 O2 126.59(19) . . ?
O1 C9 C8 118.33(18) . . ?
O2 C9 C8 115.0(2) . . ?
C11 C10 C15 118.1(3) . . ?
C11 C10 C16 121.8(2) . . ?
C15 C10 C16 120.1(2) . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11A 123(2) . . ?
C10 C11 H11A 117(2) . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12A 119(2) . . ?
C13 C12 H12A 120(2) . . ?
C12 C13 C14 119.4(3) . . ?
C12 C13 H13A 121(2) . . ?
C14 C13 H13A 119(2) . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14A 124(2) . . ?
C13 C14 H14A 115(2) . . ?
C14 C15 C10 121.1(3) . . ?
C14 C15 H15A 119(2) . . ?
C10 C15 H15A 120(2) . . ?
C10 C16 C17 114.2(2) . . ?
C10 C16 H16A 109.7(19) . . ?
C17 C16 H16A 112.7(19) . . ?
C10 C16 H16B 111.1(19) . . ?
C17 C16 H16B 104.9(19) . . ?
H16A C16 H16B 104(3) . . ?
N2 C17 C16 111.59(19) . . ?
N2 C17 C18 108.0(2) . . ?
C16 C17 C18 111.4(2) . . ?
N2 C17 H17A 106.8(14) . . ?
C16 C17 H17A 111.5(15) . . ?
C18 C17 H17A 107.2(14) . . ?
C17 N2 H2NA 108.1(19) . . ?
C17 N2 H2NB 109.0(17) . . ?
H2NA N2 H2NB 110(3) . . ?
C17 N2 H2NC 110.8(19) . . ?
H2NA N2 H2NC 111(3) . . ?
H2NB N2 H2NC 108(3) . . ?
O3 C18 O4 126.9(2) . . ?
O3 C18 C17 118.36(19) . . ?
O4 C18 C17 114.6(2) . . ?
O6 O5 H5O 96(2) . . ?
O5 O6 H6O 98(2) . . ?
O8 O7 H7O 101(3) . . ?
O7 O8 H8O 97(2) . . ?
H9OA O9 H9OB 99(6) . . ?

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
C6 C1 C2 C3 0.7(4) . . . . ?
C7 C1 C2 C3 -179.4(3) . . . . ?
C1 C2 C3 C4 -1.1(5) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C2 C1 C6 C5 0.0(4) . . . . ?
C7 C1 C6 C5 -179.9(3) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
C6 C1 C7 C8 -96.6(3) . . . . ?
C2 C1 C7 C8 83.5(3) . . . . ?
C1 C7 C8 N1 -66.1(2) . . . . ?
C1 C7 C8 C9 55.2(3) . . . . ?
N1 C8 C9 O1 23.4(3) . . . . ?
C7 C8 C9 O1 -100.0(3) . . . . ?
N1 C8 C9 O2 -158.7(2) . . . . ?
C7 C8 C9 O2 77.9(3) . . . . ?
C15 C10 C11 C12 -0.1(4) . . . . ?
C16 C10 C11 C12 -177.6(3) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 C12 C13 C14 -0.5(5) . . . . ?
C12 C13 C14 C15 0.6(5) . . . . ?
C13 C14 C15 C10 -0.3(5) . . . . ?
C11 C10 C15 C14 0.1(4) . . . . ?
C16 C10 C15 C14 177.6(3) . . . . ?
C11 C10 C16 C17 82.7(3) . . . . ?
C15 C10 C16 C17 -94.8(3) . . . . ?
C10 C16 C17 N2 -72.9(2) . . . . ?
C10 C16 C17 C18 47.9(3) . . . . ?
N2 C17 C18 O3 19.4(4) . . . . ?
C16 C17 C18 O3 -103.5(3) . . . . ?
N2 C17 C18 O4 -162.9(2) . . . . ?
C16 C17 C18 O4 74.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C8 H8A O5 0.96(3) 2.65(3) 3.238(3) 120.2(17) 4_565 yes
N1 H1NA O6 0.87(4) 2.06(3) 2.837(3) 147(3) . yes
N1 H1NB O7^a 0.95(3) 2.33(3) 3.075(3) 134(2) 2_664 yes
N1 H1NB O8^a 0.95(3) 1.99(3) 2.938(4) 172(2) 2_664 yes
N1 H1NC O2 0.87(4) 1.90(4) 2.770(2) 171(4) 1_545 yes
N2 H2NA O8^a 0.90(3) 2.07(3) 2.843(3) 143(3) 4_465 yes
N2 H2NA O9^b 0.90(3) 2.10(4) 2.89(3) 146(3) 4_465 yes
N2 H2NB O5 0.96(3) 2.39(3) 3.111(3) 131(2) 3 yes
N2 H2NB O6 0.96(3) 1.97(4) 2.917(3) 168(2) 3 yes
N2 H2NC O4 0.94(3) 1.82(3) 2.757(3) 174(3) 1_565 yes
O5 H5O O1 0.92(4) 1.79(4) 2.655(3) 157(3) 1_545 yes
O6 H6O O2 1.02(5) 1.58(5) 2.595(3) 174(4) 4_475 yes
O7^a H7O^a O3 0.84(5) 1.83(5) 2.646(3) 166(4) 4 yes
O8^a H8O^a O4 0.85(4) 1.76(4) 2.601(3) 169(4) . yes
O9^b H9OA^b O4 0.94(3) 1.76(4) 2.50(3) 133(5) . yes
O9^b H9OB^b N2 0.94(3) 2.13(7) 2.89(3) 137(10) 4_565 yes




_chemical_name_systematic        DL-Phe.H2O2
####################################################################### 
# 
# 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_DL-Asparagine_H2O2
_audit_block_doi                 10.5517/ccdc.csd.cc27y8n4
_database_code_depnum_ccdc_archive 'CCDC 2083716'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D1CE00688F 2021
loop_
_audit_author_name
_audit_author_address
'Hiroyasu Tabe'
;Osaka City University
Japan
;
_audit_update_record             
;
2021-05-14 deposited with the CCDC.	2021-07-21 downloaded from the CCDC.
;

_audit_creation_date             2020-2-14
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
#-----------------------------------------------------------------------------#

_chemical_formula_moiety         'C4 H8 N2 O3, H2 O2'
_chemical_formula_sum            'C4 H10 N2 O5'
_chemical_formula_weight         166.14

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'

_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                   4.7744(4)
_cell_length_b                   7.3961(7)
_cell_length_c                   9.8715(6)
_cell_angle_alpha                90.222(5)
_cell_angle_beta                 90.124(3)
_cell_angle_gamma                101.127(6)
_cell_volume                     342.02(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    983
_cell_measurement_theta_min      2.0631
_cell_measurement_theta_max      27.4778

_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_preparation       
'mounted on the CryoLoop with Palaton oil and placed in N2 stream at 200(2) K'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_F_000             176
_exptl_special_details           ?

_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8797
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.969

# EXPERIMENTAL DATA
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_method       'ω and φ'
_diffrn_measurement_device       'Mercury CCD (2x2 bin mode)'
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_device_details 'AFC7: Eulerian 3-circle'
_diffrn_detector_area_resol_mean 7.32
_diffrn_ambient_temperature      200(2)
_diffrn_source_power             7.5000
_diffrn_source_voltage           50.0000
_diffrn_source_current           150.0000


_diffrn_reflns_number            3934
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_min         2.063
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.987

_diffrn_measurement_details      
;
scan:
	Number of images: 600
	           Slice: -80.0000 - 100.000
	     Image width: 0.3000
	        Exp time: 1.0000
	   Rotation axis: Phi
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 0.0000
	             XTD: 44.9514
	          2theta: 20.0226
scan:
	Number of images: 160
	           Slice: -20.0000 - 28.0000
	     Image width: 0.3000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 0.0000
	             XTD: 44.9514
	          2theta: 20.0226
scan:
	Number of images: 160
	           Slice: -20.0000 - 28.0000
	     Image width: 0.3000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 90.0000
	             XTD: 44.9514
	          2theta: 20.0226
scan:
	Number of images: 160
	           Slice: -20.0000 - 28.0000
	     Image width: 0.3000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 180.0000
	             XTD: 44.9514
	          2theta: 20.0226
scan:
	Number of images: 160
	           Slice: -20.0000 - 28.0000
	     Image width: 0.3000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 270.0000
	             XTD: 44.9514
	          2theta: 20.0226
scan:
	Number of images: 140
	           Slice: -20.0000 - 22.0000
	     Image width: 0.3000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.9514
	          2theta: 20.0226
scan:
	Number of images: 140
	           Slice: -20.0000 - 22.0000
	     Image width: 0.3000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 44.9514
	          2theta: 20.0226
scan:
	Number of images: 140
	           Slice: -20.0000 - 22.0000
	     Image width: 0.3000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 44.9514
	          2theta: 20.0226
scan:
	Number of images: 140
	           Slice: -20.0000 - 22.0000
	     Image width: 0.3000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 44.9514
	          2theta: 20.0226

;

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'


#--------- REFINEMENT INFORMATION ------------------
_reflns_number_total             1544
_reflns_number_gt                1349
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0408P)²+0.1501P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1544
_refine_ls_number_parameters     140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.046

_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.
;


#---------ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS-----------
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 0.4201(3) 0.40398(17) 0.68818(13) 0.0173(3) Uani 1 1 d . . . . .
O1 O 0.3633(2) 0.54179(13) 0.75068(10) 0.0225(2) Uani 1 1 d . . . . .
O2 O 0.2968(2) 0.32900(14) 0.58672(11) 0.0281(3) Uani 1 1 d . . . . .
C2 C 0.6696(3) 0.32618(17) 0.74804(13) 0.0167(3) Uani 1 1 d . . . . .
H2A H 0.841(4) 0.412(2) 0.7301(17) 0.024(4) Uiso 1 1 d . . . . .
N1 N 0.6877(3) 0.15044(16) 0.67674(13) 0.0200(3) Uani 1 1 d . . . . .
H1NA H 0.522(5) 0.064(3) 0.687(2) 0.043(5) Uiso 1 1 d . . . . .
H1NB H 0.705(4) 0.174(3) 0.582(2) 0.037(5) Uiso 1 1 d . . . . .
H1NC H 0.841(5) 0.109(3) 0.705(2) 0.041(5) Uiso 1 1 d . . . . .
C3 C 0.6467(3) 0.29723(18) 0.90024(14) 0.0178(3) Uani 1 1 d . . . . .
H3A H 0.687(3) 0.415(2) 0.9474(17) 0.023(4) Uiso 1 1 d . . . . .
H3B H 0.794(4) 0.234(2) 0.9321(19) 0.035(5) Uiso 1 1 d . . . . .
C4 C 0.3611(3) 0.18597(16) 0.94285(13) 0.0169(3) Uani 1 1 d . . . . .
O3 O 0.2096(2) 0.08530(13) 0.85883(10) 0.0222(2) Uani 1 1 d . . . . .
N2 N 0.2860(3) 0.20002(16) 1.07094(12) 0.0219(3) Uani 1 1 d . . . . .
H2NA H 0.121(4) 0.132(3) 1.099(2) 0.037(5) Uiso 1 1 d . . . . .
H2NB H 0.398(4) 0.281(3) 1.129(2) 0.033(5) Uiso 1 1 d . . . . .
O4 O -0.0587(2) 0.81736(15) 0.64298(11) 0.0270(3) Uani 1 1 d . . . . .
H4O H -0.145(5) 0.759(3) 0.570(2) 0.049(6) Uiso 1 1 d . . . . .
O5 O 0.2398(2) 0.81605(13) 0.61063(10) 0.0223(2) Uani 1 1 d . . . . .
H5O H 0.265(4) 0.711(3) 0.658(2) 0.042(5) Uiso 1 1 d . . . . .




#--------------MOLECULAR GEOMETRY------------------
_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
C1 O2 1.2345(16) . ?
C1 O1 1.2631(15) . ?
C1 C2 1.5377(17) . ?
C2 N1 1.4929(16) . ?
C2 C3 1.5197(19) . ?
C2 H2A 0.951(18) . ?
N1 H1NA 0.92(2) . ?
N1 H1NB 0.96(2) . ?
N1 H1NC 0.89(2) . ?
C3 C4 1.5116(18) . ?
C3 H3A 0.974(17) . ?
C3 H3B 0.971(19) . ?
C4 O3 1.2450(16) . ?
C4 N2 1.3241(18) . ?
N2 H2NA 0.89(2) . ?
N2 H2NB 0.92(2) . ?
O4 O5 1.4628(13) . ?
O4 H4O 0.90(2) . ?
O5 H5O 0.94(2) . ?

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
O2 C1 O1 126.68(12) . . ?
O2 C1 C2 118.61(11) . . ?
O1 C1 C2 114.70(11) . . ?
N1 C2 C3 110.82(10) . . ?
N1 C2 C1 108.97(10) . . ?
C3 C2 C1 113.12(10) . . ?
N1 C2 H2A 107.9(10) . . ?
C3 C2 H2A 108.2(10) . . ?
C1 C2 H2A 107.7(10) . . ?
C2 N1 H1NA 111.3(13) . . ?
C2 N1 H1NB 108.8(11) . . ?
H1NA N1 H1NB 105.8(17) . . ?
C2 N1 H1NC 110.0(13) . . ?
H1NA N1 H1NC 112.1(18) . . ?
H1NB N1 H1NC 108.7(17) . . ?
C4 C3 C2 112.89(11) . . ?
C4 C3 H3A 110.8(10) . . ?
C2 C3 H3A 110.3(10) . . ?
C4 C3 H3B 107.9(11) . . ?
C2 C3 H3B 110.5(11) . . ?
H3A C3 H3B 104.1(14) . . ?
O3 C4 N2 123.03(12) . . ?
O3 C4 C3 119.82(12) . . ?
N2 C4 C3 117.15(12) . . ?
C4 N2 H2NA 118.5(13) . . ?
C4 N2 H2NB 120.8(12) . . ?
H2NA N2 H2NB 120.6(18) . . ?
O5 O4 H4O 100.1(14) . . ?
O4 O5 H5O 100.1(12) . . ?

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
O2 C1 C2 N1 -7.62(17) . . . . ?
O1 C1 C2 N1 172.39(11) . . . . ?
O2 C1 C2 C3 -131.35(13) . . . . ?
O1 C1 C2 C3 48.66(15) . . . . ?
N1 C2 C3 C4 -70.85(13) . . . . ?
C1 C2 C3 C4 51.86(14) . . . . ?
C2 C3 C4 O3 20.85(16) . . . . ?
C2 C3 C4 N2 -159.89(11) . . . . ?

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 H1NA O3 0.92(2) 2.28(2) 2.8762(15) 121.6(16) . yes
N1 H1NA O5 0.92(2) 2.19(2) 3.0092(16) 148.0(18) 1_545 yes
N1 H1NB O5 0.96(2) 1.92(2) 2.8644(16) 171.0(16) 2_666 yes
N1 H1NC O3 0.89(2) 2.36(2) 3.1818(16) 154.5(17) 1_655 yes
N1 H1NC O4 0.89(2) 2.38(2) 2.9654(15) 123.8(16) 1_645 yes
C3 H3B O3 0.971(19) 2.550(19) 3.3874(16) 144.4(15) 1_655 yes
N2 H2NA O3 0.89(2) 2.07(2) 2.9368(16) 163.5(17) 2_557 yes
N2 H2NB O1 0.92(2) 1.96(2) 2.8771(16) 178.5(17) 2_667 yes
O4 H4O O2 0.90(2) 1.77(2) 2.6647(15) 172(2) 2_566 yes
O5 H5O O1 0.94(2) 1.69(2) 2.6179(14) 170.7(19) . yes




_chemical_name_systematic        DL-Asn.H2O2
####################################################################### 
# 
# 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_L-Asparagine_H2O
_audit_block_doi                 10.5517/ccdc.csd.cc27y8p5
_database_code_depnum_ccdc_archive 'CCDC 2083717'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D1CE00688F 2021
loop_
_audit_author_name
_audit_author_address
'Hiroyasu Tabe'
;Osaka City University
Japan
;
_audit_update_record             
;
2021-05-14 deposited with the CCDC.	2021-07-21 downloaded from the CCDC.
;

_audit_creation_date             2021-4-7
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
#-----------------------------------------------------------------------------#

_chemical_formula_moiety         'C4 H8 N2 O3, H2 O'
_chemical_formula_sum            'C4 H10 N2 O4'
_chemical_formula_weight         150.14

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   5.571(2)
_cell_length_b                   9.766(4)
_cell_length_c                   11.738(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     638.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1836
_cell_measurement_theta_min      2.0855
_cell_measurement_theta_max      27.4662

_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.130
_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_preparation       
'mounted on the CryoLoop with Palaton oil and placed in N2 stream at 200(2) K'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_F_000             320
_exptl_special_details           ?

_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8723
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.982

# EXPERIMENTAL DATA
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_method       'ω and φ'
_diffrn_measurement_device       'Mercury CCD (2x2 bin mode)'
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_device_details 'AFC7: Eulerian 3-circle'
_diffrn_detector_area_resol_mean 7.32
_diffrn_ambient_temperature      200(2)
_diffrn_source_power             10.0000
_diffrn_source_voltage           50.0000
_diffrn_source_current           200.0000


_diffrn_reflns_number            4913
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_min         2.713
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_full        25.242
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999

_diffrn_measurement_details      
;
scan:
	Number of images: 600
	           Slice: -80.0000 - 100.000
	     Image width: 0.3000
	        Exp time: 8.0000
	   Rotation axis: Phi
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 0.0000
	             XTD: 54.8968
	          2theta: 25.1109
scan:
	Number of images: 200
	           Slice: -15.0000 - 45.0000
	     Image width: 0.3000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 0.0000
	             XTD: 54.8968
	          2theta: 25.1109
scan:
	Number of images: 200
	           Slice: -15.0000 - 45.0000
	     Image width: 0.3000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 90.0000
	             XTD: 54.8968
	          2theta: 25.1109
scan:
	Number of images: 200
	           Slice: -15.0000 - 45.0000
	     Image width: 0.3000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 180.0000
	             XTD: 54.8968
	          2theta: 25.1109
scan:
	Number of images: 200
	           Slice: -15.0000 - 45.0000
	     Image width: 0.3000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 90.0000
	             Phi: 270.0000
	             XTD: 54.8968
	          2theta: 25.1109

;


_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'


#--------- REFINEMENT INFORMATION ------------------
_reflns_number_total             1472
_reflns_number_gt                1447
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0451P)²+0.1513P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1472
_refine_ls_number_parameters     131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0784
_refine_ls_wR_factor_gt          0.0775
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_reflns_Friedel_coverage         0.665
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.998

_refine_ls_abs_structure_details 
;
 Flack x determined using 562 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(4)
_chemical_absolute_configuration unk

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.042

_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.
;


#---------ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS-----------
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 0.1255(3) 0.0578(2) 0.53537(14) 0.0173(4) Uani 1 1 d . . . . .
O1 O 0.0068(2) -0.04351(15) 0.49985(12) 0.0247(3) Uani 1 1 d . . . . .
O2 O 0.1199(2) 0.17552(13) 0.49569(11) 0.0213(3) Uani 1 1 d . . . . .
C2 C 0.3079(3) 0.02727(18) 0.62986(14) 0.0167(4) Uani 1 1 d . . . . .
H2A H 0.439(4) -0.025(2) 0.5950(18) 0.015(5) Uiso 1 1 d . . . . .
N1 N 0.4165(3) 0.15699(17) 0.67229(13) 0.0182(3) Uani 1 1 d . . . . .
H1NA H 0.317(5) 0.199(3) 0.726(2) 0.029(6) Uiso 1 1 d . . . . .
H1NB H 0.560(5) 0.143(3) 0.703(2) 0.036(7) Uiso 1 1 d . . . . .
H1NC H 0.444(5) 0.224(3) 0.609(2) 0.033(7) Uiso 1 1 d . . . . .
C3 C 0.2096(3) -0.05765(19) 0.72760(15) 0.0181(4) Uani 1 1 d . . . . .
H3A H 0.332(5) -0.066(3) 0.789(2) 0.029(6) Uiso 1 1 d . . . . .
H3B H 0.176(5) -0.152(3) 0.697(2) 0.028(6) Uiso 1 1 d . . . . .
C4 C -0.0170(3) 0.00186(18) 0.77939(16) 0.0174(4) Uani 1 1 d . . . . .
O3 O -0.1109(2) 0.10566(14) 0.73850(12) 0.0225(3) Uani 1 1 d . . . . .
N2 N -0.1055(3) -0.06355(18) 0.86895(14) 0.0226(3) Uani 1 1 d . . . . .
H2NA H -0.229(6) -0.028(3) 0.904(2) 0.042(8) Uiso 1 1 d . . . . .
H2NB H -0.036(6) -0.138(3) 0.900(3) 0.045(8) Uiso 1 1 d . . . . .
O4 O 0.2003(3) -0.27151(18) 0.38679(14) 0.0319(4) Uani 1 1 d . . . . .
H4OA H 0.306(7) -0.317(4) 0.428(3) 0.062(10) Uiso 1 1 d . . . . .
H4OB H 0.150(7) -0.212(4) 0.436(3) 0.061(10) Uiso 1 1 d . . . . .




#--------------MOLECULAR GEOMETRY------------------
_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
C1 O2 1.241(2) . ?
C1 O1 1.261(2) . ?
C1 C2 1.534(2) . ?
C2 N1 1.490(2) . ?
C2 C3 1.518(2) . ?
C2 H2A 0.98(2) . ?
N1 H1NA 0.94(3) . ?
N1 H1NB 0.89(3) . ?
N1 H1NC 1.00(3) . ?
C3 C4 1.517(2) . ?
C3 H3A 0.99(3) . ?
C3 H3B 1.00(3) . ?
C4 O3 1.238(2) . ?
C4 N2 1.325(2) . ?
N2 H2NA 0.87(3) . ?
N2 H2NB 0.91(3) . ?
O4 H4OA 0.88(4) . ?
O4 H4OB 0.87(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
O2 C1 O1 126.15(16) . . ?
O2 C1 C2 117.91(15) . . ?
O1 C1 C2 115.73(16) . . ?
N1 C2 C3 111.01(14) . . ?
N1 C2 C1 110.22(14) . . ?
C3 C2 C1 114.44(14) . . ?
N1 C2 H2A 106.4(13) . . ?
C3 C2 H2A 107.4(13) . . ?
C1 C2 H2A 106.9(13) . . ?
C2 N1 H1NA 111.1(16) . . ?
C2 N1 H1NB 112(2) . . ?
H1NA N1 H1NB 109(2) . . ?
C2 N1 H1NC 111.5(16) . . ?
H1NA N1 H1NC 108(2) . . ?
H1NB N1 H1NC 105(2) . . ?
C4 C3 C2 113.20(15) . . ?
C4 C3 H3A 108.1(15) . . ?
C2 C3 H3A 109.9(15) . . ?
C4 C3 H3B 109.9(15) . . ?
C2 C3 H3B 107.3(15) . . ?
H3A C3 H3B 108(2) . . ?
O3 C4 N2 123.03(18) . . ?
O3 C4 C3 120.67(17) . . ?
N2 C4 C3 116.30(16) . . ?
C4 N2 H2NA 118.3(19) . . ?
C4 N2 H2NB 123(2) . . ?
H2NA N2 H2NB 118(3) . . ?
H4OA O4 H4OB 101(3) . . ?

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
O2 C1 C2 N1 10.9(2) . . . . ?
O1 C1 C2 N1 -174.06(15) . . . . ?
O2 C1 C2 C3 136.88(16) . . . . ?
O1 C1 C2 C3 -48.1(2) . . . . ?
N1 C2 C3 C4 72.13(18) . . . . ?
C1 C2 C3 C4 -53.4(2) . . . . ?
C2 C3 C4 O3 3.5(2) . . . . ?
C2 C3 C4 N2 -176.70(16) . . . . ?

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
C2 H2A O4 0.98(2) 2.47(2) 3.325(3) 145.3(17) 3_546 yes
N1 H1NA O3 0.94(3) 2.56(3) 3.080(2) 115.5(19) . yes
N1 H1NA O4 0.94(3) 2.01(3) 2.831(2) 145(2) 2 yes
N1 H1NB O3 0.89(3) 1.92(3) 2.791(2) 168(3) 1_655 yes
N1 H1NC O2 1.00(3) 1.85(3) 2.801(2) 157(2) 3_556 yes
C3 H3B O3 1.00(3) 2.51(3) 3.357(3) 141.5(19) 4_546 yes
N2 H2NA O1 0.87(3) 2.04(3) 2.907(2) 174(3) 2_455 yes
N2 H2NB O2 0.91(3) 2.60(3) 3.275(2) 132(2) 2 yes
N2 H2NB O2 0.91(3) 2.24(3) 3.004(2) 142(3) 4_546 yes
O4 H4OA O1 0.88(4) 1.96(4) 2.819(2) 166(3) 3_546 yes
O4 H4OB O1 0.87(4) 1.97(4) 2.807(2) 161(3) . yes




_chemical_name_systematic        L-Asn.H2O
