# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_16per01
_database_code_depnum_ccdc_archive 'CCDC 1507420'
_audit_update_record             
;
2016-09-29 deposited with the CCDC.
2018-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
N-methylglycine peroxosolvate
;
_chemical_name_common            'sarcosine peroxosolvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H7 N O2, H2 O2'
_chemical_formula_sum            'C3 H9 N O4'
_chemical_formula_weight         123.11

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P c'
_symmetry_space_group_name_Hall  'P -2yc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   13.1669(7)
_cell_length_b                   6.3974(4)
_cell_length_c                   10.7817(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.6050(10)
_cell_angle_gamma                90.00
_cell_volume                     908.13(9)
_cell_formula_units_Z            6
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7405
_cell_measurement_theta_min      3.0945
_cell_measurement_theta_max      30.472

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9634
_exptl_absorpt_correction_T_max  0.9693
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10591
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0131
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         30.50
_reflns_number_total             2766
_reflns_number_gt                2700
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0526P)²+0.0181P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2766
_refine_ls_number_parameters     325
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0243
_refine_ls_wR_factor_ref         0.0669
_refine_ls_wR_factor_gt          0.0662
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O11 O 0.91975(7) 0.32810(14) 0.55751(8) 0.02500(17) Uani 1 1 d . . .
O12 O 1.06642(7) 0.43582(15) 0.47590(9) 0.02721(18) Uani 1 1 d . . .
N1 N 0.91166(7) -0.02708(15) 0.42951(9) 0.01933(17) Uani 1 1 d . . .
C11 C 0.99453(8) 0.30714(17) 0.48827(10) 0.01893(18) Uani 1 1 d . . .
C12 C 1.00037(8) 0.11080(17) 0.40891(10) 0.01876(18) Uani 1 1 d . . .
C13 C 0.90630(11) -0.2043(2) 0.34027(13) 0.0292(2) Uani 1 1 d . . .
H1A H 0.9150(15) -0.079(3) 0.509(2) 0.032(4) Uiso 1 1 d . . .
H1B H 0.8576(16) 0.042(3) 0.4218(19) 0.033(5) Uiso 1 1 d . . .
H12A H 1.0590(15) 0.034(3) 0.4280(19) 0.031(4) Uiso 1 1 d . . .
H12B H 1.0003(17) 0.155(4) 0.328(2) 0.041(5) Uiso 1 1 d . . .
H13A H 0.9685(18) -0.279(4) 0.349(2) 0.040(6) Uiso 1 1 d . . .
H13B H 0.8503(18) -0.290(3) 0.357(2) 0.040(5) Uiso 1 1 d . . .
H13C H 0.8994(17) -0.154(4) 0.267(2) 0.040(5) Uiso 1 1 d . . .
O21 O 0.57687(7) 0.28724(16) 0.37058(9) 0.02716(18) Uani 1 1 d . . .
O22 O 0.73447(7) 0.16184(17) 0.35526(8) 0.02875(19) Uani 1 1 d . . .
N2 N 0.57599(7) 0.29469(15) 0.61644(9) 0.01914(17) Uani 1 1 d . . .
C21 C 0.65874(8) 0.22223(16) 0.41551(11) 0.01947(19) Uani 1 1 d . . .
C22 C 0.66822(8) 0.20994(18) 0.55623(10) 0.02038(19) Uani 1 1 d . . .
C23 C 0.57411(11) 0.2540(2) 0.75253(12) 0.0272(2) Uani 1 1 d . . .
H2A H 0.5743(14) 0.434(3) 0.6037(18) 0.027(4) Uiso 1 1 d . . .
H2B H 0.5230(15) 0.238(3) 0.5834(19) 0.025(4) Uiso 1 1 d . . .
H22A H 0.7258(19) 0.293(4) 0.586(2) 0.049(6) Uiso 1 1 d . . .
H22B H 0.6735(16) 0.068(4) 0.580(2) 0.035(5) Uiso 1 1 d . . .
H23A H 0.5725(18) 0.112(4) 0.761(2) 0.050(6) Uiso 1 1 d . . .
H23B H 0.6304(19) 0.311(4) 0.792(2) 0.046(6) Uiso 1 1 d . . .
H23C H 0.5158(18) 0.320(4) 0.790(2) 0.045(6) Uiso 1 1 d . . .
O31 O 0.39519(6) 0.11307(14) 0.55471(9) 0.02503(17) Uani 1 1 d . . .
O32 O 0.24511(7) 0.06396(14) 0.46043(9) 0.02722(18) Uani 1 1 d . . .
N3 N 0.24333(7) 0.42174(14) 0.33997(8) 0.01762(16) Uani 1 1 d . . .
C31 C 0.32356(7) 0.16685(17) 0.48315(10) 0.01773(18) Uani 1 1 d . . .
C32 C 0.33368(7) 0.37795(16) 0.41938(10) 0.01838(18) Uani 1 1 d . . .
C33 C 0.24607(10) 0.63129(19) 0.28049(11) 0.0255(2) Uani 1 1 d . . .
H3A H 0.2399(14) 0.323(3) 0.2827(18) 0.026(4) Uiso 1 1 d . . .
H3B H 0.1920(14) 0.409(3) 0.3785(18) 0.023(4) Uiso 1 1 d . . .
H32A H 0.3909(16) 0.375(3) 0.3661(19) 0.034(5) Uiso 1 1 d . . .
H32B H 0.3393(15) 0.478(3) 0.482(2) 0.031(4) Uiso 1 1 d . . .
H33A H 0.2497(15) 0.731(3) 0.341(2) 0.029(5) Uiso 1 1 d . . .
H33B H 0.3062(18) 0.639(4) 0.233(2) 0.045(6) Uiso 1 1 d . . .
H33C H 0.1873(16) 0.643(3) 0.232(2) 0.037(5) Uiso 1 1 d . . .
O1 O 0.88543(6) 0.28896(15) 0.14211(9) 0.02459(17) Uani 1 1 d . . .
O2 O 0.77486(7) 0.28285(16) 0.12250(9) 0.02828(19) Uani 1 1 d . . .
H1 H 0.9010(16) 0.418(4) 0.114(2) 0.037(5) Uiso 1 1 d . . .
H2 H 0.7578(17) 0.254(3) 0.195(2) 0.035(5) Uiso 1 1 d . . .
O3 O 0.54494(7) 0.26326(14) 0.12950(9) 0.02428(17) Uani 1 1 d . . .
O4 O 0.43358(7) 0.28186(14) 0.13102(10) 0.02694(18) Uani 1 1 d . . .
H3 H 0.5602(16) 0.272(3) 0.210(2) 0.034(5) Uiso 1 1 d . . .
H4 H 0.4199(18) 0.165(4) 0.104(2) 0.039(5) Uiso 1 1 d . . .
O5 O 0.21153(7) 0.24876(16) 0.10919(10) 0.0288(2) Uani 1 1 d . . .
O6 O 0.10071(7) 0.23925(16) 0.12388(10) 0.02791(18) Uani 1 1 d . . .
H5 H 0.2196(15) 0.141(4) 0.067(2) 0.033(5) Uiso 1 1 d . . .
H6 H 0.0857(15) 0.341(3) 0.0837(19) 0.029(4) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O11 C11 1.2491(13) . ?
O12 C11 1.2626(14) . ?
N1 C12 1.4822(13) . ?
N1 C13 1.4882(15) . ?
N1 H1A 0.92(2) . ?
N1 H1B 0.84(2) . ?
C11 C12 1.5222(15) . ?
C12 H12A 0.94(2) . ?
C12 H12B 0.92(2) . ?
C13 H13A 0.95(2) . ?
C13 H13B 0.94(2) . ?
C13 H13C 0.86(3) . ?
O21 C21 1.2485(14) . ?
O22 C21 1.2567(14) . ?
N2 C22 1.4855(13) . ?
N2 C23 1.4906(15) . ?
N2 H2A 0.90(2) . ?
N2 H2B 0.86(2) . ?
C21 C22 1.5231(15) . ?
C22 H22A 0.98(3) . ?
C22 H22B 0.94(2) . ?
C23 H23A 0.92(3) . ?
C23 H23B 0.92(3) . ?
C23 H23C 0.97(2) . ?
O31 C31 1.2601(13) . ?
O32 C31 1.2470(13) . ?
N3 C32 1.4850(13) . ?
N3 C33 1.4867(14) . ?
N3 H3A 0.89(2) . ?
N3 H3B 0.801(19) . ?
C31 C32 1.5219(15) . ?
C32 H32A 0.95(2) . ?
C32 H32B 0.93(2) . ?
C33 H33A 0.92(2) . ?
C33 H33B 0.95(2) . ?
C33 H33C 0.93(2) . ?
O1 O2 1.4695(12) . ?
O1 H1 0.90(2) . ?
O2 H2 0.83(2) . ?
O3 O4 1.4713(12) . ?
O3 H3 0.89(2) . ?
O4 H4 0.82(3) . ?
O5 O6 1.4705(12) . ?
O5 H5 0.83(2) . ?
O6 H6 0.80(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
C12 N1 C13 112.87(9) . . ?
C12 N1 H1A 108.9(12) . . ?
C13 N1 H1A 109.4(13) . . ?
C12 N1 H1B 109.9(15) . . ?
C13 N1 H1B 107.6(14) . . ?
H1A N1 H1B 108.2(19) . . ?
O11 C11 O12 126.14(11) . . ?
O11 C11 C12 117.99(10) . . ?
O12 C11 C12 115.87(10) . . ?
N1 C12 C11 111.24(8) . . ?
N1 C12 H12A 107.8(12) . . ?
C11 C12 H12A 110.8(13) . . ?
N1 C12 H12B 109.4(15) . . ?
C11 C12 H12B 106.3(15) . . ?
H12A C12 H12B 111.3(18) . . ?
N1 C13 H13A 106.7(14) . . ?
N1 C13 H13B 110.7(14) . . ?
H13A C13 H13B 111(2) . . ?
N1 C13 H13C 108.5(16) . . ?
H13A C13 H13C 111(2) . . ?
H13B C13 H13C 109(2) . . ?
C22 N2 C23 112.87(9) . . ?
C22 N2 H2A 108.2(12) . . ?
C23 N2 H2A 108.8(12) . . ?
C22 N2 H2B 109.1(13) . . ?
C23 N2 H2B 108.2(13) . . ?
H2A N2 H2B 109.6(17) . . ?
O21 C21 O22 126.04(11) . . ?
O21 C21 C22 117.72(10) . . ?
O22 C21 C22 116.23(10) . . ?
N2 C22 C21 110.95(8) . . ?
N2 C22 H22A 107.0(15) . . ?
C21 C22 H22A 110.8(15) . . ?
N2 C22 H22B 106.7(13) . . ?
C21 C22 H22B 109.1(13) . . ?
H22A C22 H22B 112.2(19) . . ?
N2 C23 H23A 106.1(16) . . ?
N2 C23 H23B 111.2(16) . . ?
H23A C23 H23B 111(2) . . ?
N2 C23 H23C 110.8(16) . . ?
H23A C23 H23C 112(2) . . ?
H23B C23 H23C 106(2) . . ?
C32 N3 C33 113.32(8) . . ?
C32 N3 H3A 107.5(12) . . ?
C33 N3 H3A 110.3(12) . . ?
C32 N3 H3B 110.9(13) . . ?
C33 N3 H3B 109.9(13) . . ?
H3A N3 H3B 104.5(18) . . ?
O32 C31 O31 126.10(10) . . ?
O32 C31 C32 117.13(9) . . ?
O31 C31 C32 116.77(9) . . ?
N3 C32 C31 110.76(8) . . ?
N3 C32 H32A 106.8(13) . . ?
C31 C32 H32A 109.3(13) . . ?
N3 C32 H32B 110.0(13) . . ?
C31 C32 H32B 107.0(13) . . ?
H32A C32 H32B 112.9(17) . . ?
N3 C33 H33A 109.0(13) . . ?
N3 C33 H33B 107.8(15) . . ?
H33A C33 H33B 108(2) . . ?
N3 C33 H33C 107.0(14) . . ?
H33A C33 H33C 112.1(19) . . ?
H33B C33 H33C 113(2) . . ?
O2 O1 H1 101.8(13) . . ?
O1 O2 H2 98.5(16) . . ?
O4 O3 H3 101.5(13) . . ?
O3 O4 H4 97.9(17) . . ?
O6 O5 H5 99.1(14) . . ?
O5 O6 H6 98.4(14) . . ?

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
C13 N1 C12 C11 171.31(10) . . . . ?
O11 C11 C12 N1 -0.09(14) . . . . ?
O12 C11 C12 N1 -179.16(10) . . . . ?
C23 N2 C22 C21 170.46(10) . . . . ?
O21 C21 C22 N2 -3.81(14) . . . . ?
O22 C21 C22 N2 177.36(10) . . . . ?
C33 N3 C32 C31 176.82(9) . . . . ?
O32 C31 C32 N3 0.50(13) . . . . ?
O31 C31 C32 N3 -179.06(9) . . . . ?
H1 O1 O2 H2 -124(2) . . . . ?
H3 O3 O4 H4 -116(2) . . . . ?
H5 O5 O6 H6 -113(2) . . . . ?

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
O1 H1 O11 0.90(2) 1.75(2) 2.6545(13) 175(2) 2_564
O2 H2 O22 0.83(2) 1.86(2) 2.6847(14) 172(2) .
O3 H3 O21 0.89(2) 1.74(2) 2.6331(13) 174(2) .
O4 H4 O31 0.82(3) 1.88(3) 2.7031(13) 174(2) 2_554
O5 H5 O32 0.83(2) 1.78(2) 2.6048(13) 172(2) 2_554
O6 H6 O12 0.80(2) 1.86(2) 2.6562(13) 172(2) 2_464
N1 H1A O1 0.92(2) 2.00(2) 2.8630(14) 153.9(18) 2
N1 H1B O22 0.84(2) 1.93(2) 2.7396(13) 163(2) .
N2 H2A O3 0.90(2) 1.99(2) 2.8611(13) 160.5(17) 2_565
N2 H2B O31 0.86(2) 1.89(2) 2.7252(13) 165(2) .
N3 H3A O5 0.89(2) 1.96(2) 2.7512(13) 147.6(17) .
N3 H3B O12 0.801(19) 1.975(19) 2.7666(13) 169.1(19) 1_455

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        30.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.037
_chemical_properties_physical    ', Moisture-sensitive'
####################################################################### 
# 
# 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_16per06
_database_code_depnum_ccdc_archive 'CCDC 1507421'
_audit_update_record             
;
2016-09-29 deposited with the CCDC.
2018-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
3-phenylserine peroxosolvate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H11 N O3, H2 O2'
_chemical_formula_sum            'C9 H13 N O5'
_chemical_formula_weight         215.20

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'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P -4 21 c'
_symmetry_space_group_name_Hall  'P -4 2n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+1/2, z+1/2'

_cell_length_a                   18.7167(5)
_cell_length_b                   18.7167(5)
_cell_length_c                   5.7741(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2022.75(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5722
_cell_measurement_theta_min      2.433
_cell_measurement_theta_max      27.166

_exptl_crystal_description       needles
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9572
_exptl_absorpt_correction_T_max  0.9942
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            23552
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         29.98
_reflns_number_total             1693
_reflns_number_gt                1518
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0489P)²+0.1984P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1693
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0778
_refine_ls_wR_factor_gt          0.0741
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.08181(6) 0.18154(6) -0.34194(19) 0.0192(2) Uani 1 1 d . . .
O2 O -0.02675(5) 0.08222(6) -0.22634(19) 0.0169(2) Uani 1 1 d . . .
O3 O 0.07835(6) 0.18139(6) 0.0129(2) 0.0196(2) Uani 1 1 d . . .
N1 N -0.03815(7) 0.11746(6) 0.2300(2) 0.0142(2) Uani 1 1 d . . .
C1 C -0.05283(7) 0.14247(8) -0.1905(2) 0.0141(3) Uani 1 1 d . . .
C2 C -0.04676(7) 0.17445(7) 0.0535(2) 0.0135(3) Uani 1 1 d . . .
C3 C 0.01773(7) 0.22544(7) 0.0537(2) 0.0151(3) Uani 1 1 d . . .
C4 C 0.02418(8) 0.27182(8) 0.2678(3) 0.0178(3) Uani 1 1 d . . .
C5 C 0.08228(9) 0.26772(9) 0.4173(3) 0.0230(3) Uani 1 1 d . . .
C6 C 0.08947(11) 0.31682(11) 0.5975(3) 0.0314(4) Uani 1 1 d . . .
C7 C 0.03831(12) 0.36859(10) 0.6328(3) 0.0370(5) Uani 1 1 d . . .
C8 C -0.02075(12) 0.37158(10) 0.4891(4) 0.0359(4) Uani 1 1 d . . .
C9 C -0.02801(9) 0.32391(9) 0.3056(3) 0.0263(3) Uani 1 1 d . . .
H2 H -0.0912(9) 0.2011(10) 0.082(4) 0.013(4) Uiso 1 1 d . . .
H3 H 0.0110(9) 0.2576(9) -0.079(3) 0.011(4) Uiso 1 1 d . . .
H5 H 0.1205(13) 0.2312(12) 0.393(4) 0.035(6) Uiso 1 1 d . . .
H6 H 0.1287(13) 0.3164(13) 0.695(5) 0.048(7) Uiso 1 1 d . . .
H7 H 0.0421(13) 0.4022(12) 0.751(5) 0.046(7) Uiso 1 1 d . . .
H8 H -0.0593(13) 0.4057(13) 0.508(5) 0.051(8) Uiso 1 1 d . . .
H9 H -0.0696(12) 0.3233(12) 0.199(5) 0.038(6) Uiso 1 1 d . . .
H13 H 0.1146(11) 0.2035(11) 0.032(4) 0.018(5) Uiso 1 1 d . . .
H31 H -0.0669(11) 0.0788(11) 0.200(4) 0.028(5) Uiso 1 1 d . . .
H32 H 0.0041(12) 0.0953(11) 0.224(4) 0.025(5) Uiso 1 1 d . . .
H33 H -0.0491(11) 0.1354(11) 0.374(4) 0.029(6) Uiso 1 1 d . . .
O11 O 0.27217(6) 0.17908(7) 0.2220(2) 0.0281(3) Uani 1 1 d . . .
O12 O 0.22680(7) 0.22107(7) 0.0651(2) 0.0295(3) Uani 1 1 d . . .
H11 H 0.2425(12) 0.1443(13) 0.259(5) 0.040(6) Uiso 1 1 d . . .
H12 H 0.2584(14) 0.2254(15) -0.058(6) 0.052(7) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2622(18) . ?
O2 C1 1.2461(18) . ?
O3 C3 1.4221(17) . ?
O3 H13 0.80(2) . ?
N1 C2 1.4842(18) . ?
N1 H31 0.92(2) . ?
N1 H32 0.89(2) . ?
N1 H33 0.92(2) . ?
C1 C2 1.5353(19) . ?
C2 C3 1.5387(19) . ?
C2 H2 0.984(18) . ?
C3 C4 1.516(2) . ?
C3 H3 0.984(18) . ?
C4 C5 1.390(2) . ?
C4 C9 1.397(2) . ?
C5 C6 1.395(2) . ?
C5 H5 1.00(2) . ?
C6 C7 1.377(3) . ?
C6 H6 0.92(3) . ?
C7 C8 1.383(3) . ?
C7 H7 0.93(3) . ?
C8 C9 1.392(2) . ?
C8 H8 0.97(3) . ?
C9 H9 0.99(2) . ?
O11 O12 1.4697(18) . ?
O11 H11 0.88(2) . ?
O12 H12 0.93(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
C3 O3 H13 110.7(14) . . ?
C2 N1 H31 112.0(15) . . ?
C2 N1 H32 113.7(14) . . ?
H31 N1 H32 98.4(18) . . ?
C2 N1 H33 109.4(14) . . ?
H31 N1 H33 109(2) . . ?
H32 N1 H33 114(2) . . ?
O2 C1 O1 125.29(14) . . ?
O2 C1 C2 118.43(12) . . ?
O1 C1 C2 116.21(12) . . ?
N1 C2 C1 110.98(11) . . ?
N1 C2 C3 111.11(11) . . ?
C1 C2 C3 107.48(11) . . ?
N1 C2 H2 109.8(12) . . ?
C1 C2 H2 106.9(12) . . ?
C3 C2 H2 110.4(10) . . ?
O3 C3 C4 113.81(12) . . ?
O3 C3 C2 105.44(11) . . ?
C4 C3 C2 114.72(11) . . ?
O3 C3 H3 109.2(10) . . ?
C4 C3 H3 107.2(10) . . ?
C2 C3 H3 106.2(10) . . ?
C5 C4 C9 119.23(15) . . ?
C5 C4 C3 122.49(14) . . ?
C9 C4 C3 118.13(14) . . ?
C4 C5 C6 120.14(17) . . ?
C4 C5 H5 120.6(14) . . ?
C6 C5 H5 119.2(14) . . ?
C7 C6 C5 120.45(18) . . ?
C7 C6 H6 117.8(16) . . ?
C5 C6 H6 121.7(16) . . ?
C6 C7 C8 119.70(17) . . ?
C6 C7 H7 122.1(16) . . ?
C8 C7 H7 118.2(16) . . ?
C7 C8 C9 120.56(19) . . ?
C7 C8 H8 123.7(17) . . ?
C9 C8 H8 115.7(17) . . ?
C8 C9 C4 119.87(17) . . ?
C8 C9 H9 123.8(14) . . ?
C4 C9 H9 116.3(14) . . ?
O12 O11 H11 100.5(16) . . ?
O11 O12 H12 98.7(17) . . ?

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 -24.07(17) . . . . ?
O1 C1 C2 N1 158.71(12) . . . . ?
O2 C1 C2 C3 97.62(14) . . . . ?
O1 C1 C2 C3 -79.60(15) . . . . ?
N1 C2 C3 O3 57.33(14) . . . . ?
C1 C2 C3 O3 -64.28(14) . . . . ?
N1 C2 C3 C4 -68.70(15) . . . . ?
C1 C2 C3 C4 169.69(12) . . . . ?
O3 C3 C4 C5 -3.96(19) . . . . ?
C2 C3 C4 C5 117.60(16) . . . . ?
O3 C3 C4 C9 171.42(13) . . . . ?
C2 C3 C4 C9 -67.02(17) . . . . ?
C9 C4 C5 C6 -2.3(2) . . . . ?
C3 C4 C5 C6 172.98(14) . . . . ?
C4 C5 C6 C7 1.7(2) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C6 C7 C8 C9 -1.7(3) . . . . ?
C7 C8 C9 C4 1.0(3) . . . . ?
C5 C4 C9 C8 1.0(2) . . . . ?
C3 C4 C9 C8 -174.49(15) . . . . ?
H11 O11 O12 H12 -130(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
O11 H11 O1 0.88(2) 1.70(3) 2.5830(17) 176(2) 3
O12 H12 O11 0.93(3) 1.73(3) 2.6539(19) 175(3) 7_554
O3 H13 O12 0.80(2) 2.13(2) 2.8918(16) 157.6(19) .
N1 H31 O2 0.92(2) 2.00(2) 2.8224(16) 148.0(19) 4
N1 H32 O2 0.89(2) 1.95(2) 2.8209(17) 166.2(19) 3
N1 H33 O1 0.92(2) 1.95(2) 2.8661(16) 172(2) 1_556

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        29.98
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.039
_chemical_properties_physical    ', Moisture-sensitive'
