# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_FO5315
_database_code_depnum_ccdc_archive 'CCDC 1004515'
_audit_update_record             
;
2014-12-17 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H27 N O4'
_chemical_formula_sum            'C18 H27 N O4'
_chemical_formula_weight         321.41

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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'

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

_cell_length_a                   15.6931(3)
_cell_length_b                   21.8725(4)
_cell_length_c                   5.0383(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1729.38(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.075
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.048
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           ?

_diffrn_ambient_temperature      133(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  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12151
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_sigmaI/netI    0.0499
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3985
_reflns_number_gt                3378
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       DENZO
_computing_data_reduction        DENZO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97

_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)+(0.0215P)²+0.6181P] 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_abs_structure_details 
;
 Flack x determined using 1165 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.4(8)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3985
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.0946
_refine_ls_wR_factor_gt          0.0881
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_restrained_S_all      1.164
_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
O1 O 1.13077(10) 0.24872(7) -0.0829(3) 0.0289(3) Uani 1 1 d . . .
O2 O 1.13442(10) 0.49159(7) -0.2775(3) 0.0335(4) Uani 1 1 d . . .
O3 O 0.92931(8) 0.25831(6) 0.3896(3) 0.0234(3) Uani 1 1 d . . .
O4 O 0.90457(10) 0.19541(8) 0.0443(3) 0.0364(4) Uani 1 1 d . . .
N1 N 1.09928(11) 0.23189(8) 0.3472(3) 0.0197(4) Uani 1 1 d . . .
H1N1 H 1.1078(14) 0.2415(11) 0.507(5) 0.030(6) Uiso 1 1 d . . .
C1 C 1.14233(12) 0.26073(9) 0.1540(4) 0.0195(4) Uani 1 1 d . . .
C2 C 1.20599(13) 0.30825(9) 0.2391(4) 0.0205(4) Uani 1 1 d . . .
H2B H 1.2209(13) 0.3013(9) 0.428(5) 0.020(5) Uiso 1 1 d . . .
H2A H 1.2564(13) 0.3018(9) 0.137(5) 0.020(5) Uiso 1 1 d . . .
C3 C 1.17563(12) 0.37498(9) 0.2121(4) 0.0184(4) Uani 1 1 d . . .
H3 H 1.1310(12) 0.3856(9) 0.351(4) 0.018(5) Uiso 1 1 d . . .
C4 C 1.25129(13) 0.41943(10) 0.2421(5) 0.0240(5) Uani 1 1 d . . .
H4A H 1.3004(13) 0.4025(10) 0.133(5) 0.023(6) Uiso 1 1 d . . .
H4B H 1.2693(15) 0.4227(11) 0.439(5) 0.036(7) Uiso 1 1 d . . .
C5 C 1.21961(15) 0.47922(10) 0.1215(5) 0.0273(5) Uani 1 1 d . . .
H5B H 1.1845(15) 0.5026(11) 0.248(5) 0.035(7) Uiso 1 1 d . . .
H5A H 1.2646(16) 0.5080(11) 0.060(5) 0.043(7) Uiso 1 1 d . . .
C6 C 1.15984(13) 0.45994(10) -0.0967(4) 0.0240(5) Uani 1 1 d . . .
C7 C 1.13469(13) 0.39290(9) -0.0556(4) 0.0203(4) Uani 1 1 d . . .
H7 H 1.1620(12) 0.3693(10) -0.196(4) 0.016(5) Uiso 1 1 d . . .
C8 C 1.03782(13) 0.38436(10) -0.0801(4) 0.0242(5) Uani 1 1 d . . .
H8B H 1.0237(14) 0.3389(11) -0.107(5) 0.031(6) Uiso 1 1 d . . .
H8A H 1.0191(13) 0.4058(11) -0.243(4) 0.026(6) Uiso 1 1 d . . .
C9 C 0.99035(13) 0.41068(10) 0.1524(4) 0.0232(4) Uani 1 1 d . . .
H9 H 1.0180(14) 0.4439(11) 0.236(5) 0.030(6) Uiso 1 1 d . . .
C10 C 0.91634(13) 0.39160(10) 0.2499(4) 0.0249(4) Uani 1 1 d . . .
H10 H 0.8945(14) 0.4116(10) 0.401(5) 0.031(6) Uiso 1 1 d . . .
C11 C 0.86196(13) 0.34130(10) 0.1435(4) 0.0258(5) Uani 1 1 d . . .
H11B H 0.8843(13) 0.3239(9) -0.030(4) 0.019(5) Uiso 1 1 d . . .
H11A H 0.8047(15) 0.3571(10) 0.103(5) 0.030(6) Uiso 1 1 d . . .
C12 C 0.84886(13) 0.28917(10) 0.3399(5) 0.0253(5) Uani 1 1 d . . .
H12B H 0.8298(12) 0.3049(9) 0.524(4) 0.019(5) Uiso 1 1 d . . .
H12A H 0.8067(14) 0.2588(11) 0.273(5) 0.028(6) Uiso 1 1 d . . .
C13 C 0.94998(13) 0.21293(10) 0.2214(4) 0.0226(4) Uani 1 1 d . . .
C14 C 1.03625(12) 0.18512(9) 0.2864(4) 0.0202(4) Uani 1 1 d . . .
H14 H 1.0526(13) 0.1643(9) 0.128(5) 0.021(5) Uiso 1 1 d . . .
C15 C 1.02825(13) 0.13803(10) 0.5121(4) 0.0249(5) Uani 1 1 d . . .
H15 H 1.0055(14) 0.1601(10) 0.670(4) 0.025(6) Uiso 1 1 d . . .
C16 C 0.96519(16) 0.08783(12) 0.4346(6) 0.0377(6) Uani 1 1 d . . .
H16C H 0.9047(19) 0.1034(13) 0.403(6) 0.056(8) Uiso 1 1 d . . .
H16B H 0.9833(18) 0.0648(14) 0.266(6) 0.060(9) Uiso 1 1 d . . .
H16A H 0.9596(16) 0.0566(13) 0.580(6) 0.054(9) Uiso 1 1 d . . .
C17 C 1.11517(14) 0.11109(11) 0.5882(4) 0.0264(5) Uani 1 1 d . . .
H17B H 1.1507(13) 0.1435(10) 0.667(4) 0.023(6) Uiso 1 1 d . . .
H17A H 1.1030(15) 0.0806(11) 0.729(5) 0.035(7) Uiso 1 1 d . . .
C18 C 1.16395(17) 0.08072(12) 0.3632(5) 0.0349(6) Uani 1 1 d . . .
H18C H 1.2193(15) 0.0637(10) 0.418(5) 0.033(6) Uiso 1 1 d . . .
H18B H 1.1794(15) 0.1089(12) 0.218(5) 0.038(7) Uiso 1 1 d . . .
H18A H 1.1299(18) 0.0469(14) 0.281(6) 0.062(9) 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 1.235(2) . ?
O2 C6 1.212(3) . ?
O3 C13 1.345(2) . ?
O3 C12 1.453(2) . ?
O4 C13 1.205(2) . ?
N1 C1 1.342(3) . ?
N1 C14 1.456(2) . ?
N1 H1N1 0.84(3) . ?
C1 C2 1.504(3) . ?
C2 C3 1.541(3) . ?
C2 H2B 0.99(2) . ?
C2 H2A 0.95(2) . ?
C3 C4 1.542(3) . ?
C3 C7 1.544(3) . ?
C3 H3 1.02(2) . ?
C4 C5 1.525(3) . ?
C4 H4A 1.02(2) . ?
C4 H4B 1.04(3) . ?
C5 C6 1.505(3) . ?
C5 H5B 0.99(3) . ?
C5 H5A 1.00(3) . ?
C6 C7 1.533(3) . ?
C7 C8 1.537(3) . ?
C7 H7 0.98(2) . ?
C8 C9 1.503(3) . ?
C8 H8B 1.03(2) . ?
C8 H8A 0.99(2) . ?
C9 C10 1.328(3) . ?
C9 H9 0.95(2) . ?
C10 C11 1.492(3) . ?
C10 H10 0.94(2) . ?
C11 C12 1.524(3) . ?
C11 H11B 1.01(2) . ?
C11 H11A 0.98(2) . ?
C12 H12B 1.04(2) . ?
C12 H12A 1.00(2) . ?
C13 C14 1.520(3) . ?
C14 C15 1.540(3) . ?
C14 H14 0.95(2) . ?
C15 C16 1.529(3) . ?
C15 C17 1.534(3) . ?
C15 H15 1.00(2) . ?
C16 H16C 1.02(3) . ?
C16 H16B 1.03(3) . ?
C16 H16A 1.00(3) . ?
C17 C18 1.521(3) . ?
C17 H17B 0.98(2) . ?
C17 H17A 0.99(2) . ?
C18 H18C 0.98(2) . ?
C18 H18B 0.99(3) . ?
C18 H18A 1.00(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
C13 O3 C12 116.34(16) . . ?
C1 N1 C14 121.30(17) . . ?
C1 N1 H1N1 119.7(16) . . ?
C14 N1 H1N1 119.0(16) . . ?
O1 C1 N1 121.79(18) . . ?
O1 C1 C2 121.31(18) . . ?
N1 C1 C2 116.90(17) . . ?
C1 C2 C3 115.08(16) . . ?
C1 C2 H2B 108.9(12) . . ?
C3 C2 H2B 107.7(12) . . ?
C1 C2 H2A 107.1(13) . . ?
C3 C2 H2A 110.5(13) . . ?
H2B C2 H2A 107.3(18) . . ?
C4 C3 C2 110.51(16) . . ?
C4 C3 C7 104.23(16) . . ?
C2 C3 C7 116.48(17) . . ?
C4 C3 H3 108.7(11) . . ?
C2 C3 H3 111.6(12) . . ?
C7 C3 H3 104.8(12) . . ?
C5 C4 C3 104.51(17) . . ?
C5 C4 H4A 110.1(13) . . ?
C3 C4 H4A 107.5(12) . . ?
C5 C4 H4B 114.4(13) . . ?
C3 C4 H4B 110.3(13) . . ?
H4A C4 H4B 109.7(18) . . ?
C6 C5 C4 104.71(18) . . ?
C6 C5 H5B 105.7(14) . . ?
C4 C5 H5B 111.6(14) . . ?
C6 C5 H5A 113.0(14) . . ?
C4 C5 H5A 115.8(14) . . ?
H5B C5 H5A 105.7(19) . . ?
O2 C6 C5 126.5(2) . . ?
O2 C6 C7 124.3(2) . . ?
C5 C6 C7 109.24(17) . . ?
C6 C7 C8 111.11(17) . . ?
C6 C7 C3 104.70(16) . . ?
C8 C7 C3 116.79(17) . . ?
C6 C7 H7 107.2(12) . . ?
C8 C7 H7 108.2(12) . . ?
C3 C7 H7 108.4(12) . . ?
C9 C8 C7 112.42(18) . . ?
C9 C8 H8B 111.5(13) . . ?
C7 C8 H8B 110.0(12) . . ?
C9 C8 H8A 108.6(13) . . ?
C7 C8 H8A 107.6(13) . . ?
H8B C8 H8A 106.5(18) . . ?
C10 C9 C8 127.0(2) . . ?
C10 C9 H9 118.5(14) . . ?
C8 C9 H9 114.5(14) . . ?
C9 C10 C11 126.8(2) . . ?
C9 C10 H10 118.1(14) . . ?
C11 C10 H10 115.1(14) . . ?
C10 C11 C12 113.33(18) . . ?
C10 C11 H11B 112.9(11) . . ?
C12 C11 H11B 108.9(12) . . ?
C10 C11 H11A 109.8(13) . . ?
C12 C11 H11A 105.8(14) . . ?
H11B C11 H11A 105.6(18) . . ?
O3 C12 C11 110.01(17) . . ?
O3 C12 H12B 104.5(11) . . ?
C11 C12 H12B 111.9(12) . . ?
O3 C12 H12A 109.0(13) . . ?
C11 C12 H12A 111.5(13) . . ?
H12B C12 H12A 109.6(17) . . ?
O4 C13 O3 123.98(19) . . ?
O4 C13 C14 124.00(19) . . ?
O3 C13 C14 112.00(17) . . ?
N1 C14 C13 111.68(16) . . ?
N1 C14 C15 111.71(16) . . ?
C13 C14 C15 110.74(16) . . ?
N1 C14 H14 109.2(12) . . ?
C13 C14 H14 104.5(12) . . ?
C15 C14 H14 108.7(13) . . ?
C16 C15 C17 111.31(19) . . ?
C16 C15 C14 110.15(19) . . ?
C17 C15 C14 111.65(17) . . ?
C16 C15 H15 108.6(13) . . ?
C17 C15 H15 107.8(12) . . ?
C14 C15 H15 107.2(13) . . ?
C15 C16 H16C 113.7(16) . . ?
C15 C16 H16B 112.6(16) . . ?
H16C C16 H16B 107(2) . . ?
C15 C16 H16A 111.1(16) . . ?
H16C C16 H16A 105(2) . . ?
H16B C16 H16A 107(2) . . ?
C18 C17 C15 115.40(19) . . ?
C18 C17 H17B 109.1(12) . . ?
C15 C17 H17B 109.2(12) . . ?
C18 C17 H17A 109.6(14) . . ?
C15 C17 H17A 105.4(14) . . ?
H17B C17 H17A 107.9(19) . . ?
C17 C18 H18C 113.6(15) . . ?
C17 C18 H18B 113.8(15) . . ?
H18C C18 H18B 103.1(19) . . ?
C17 C18 H18A 111.2(17) . . ?
H18C C18 H18A 108(2) . . ?
H18B C18 H18A 107(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
N1 H1N1 O1 0.84(3) 2.10(3) 2.937(2) 170(2) 1_556

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_FO5152
_database_code_depnum_ccdc_archive 'CCDC 1004516'
_audit_update_record             
;
2014-12-17 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H27 N O4'
_chemical_formula_sum            'C18 H27 N O4'
_chemical_formula_weight         321.41

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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   5.7917(3)
_cell_length_b                   15.4852(7)
_cell_length_c                   18.6976(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1676.91(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           ?

_diffrn_ambient_temperature      133(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  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27196
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         27.52
_reflns_number_total             3401
_reflns_number_gt                3299
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       DENZO
_computing_data_reduction        DENZO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97

_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)+(0.0497P)²+0.2791P] 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_abs_structure_details 
;
 Flack x determined using 1330 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3401
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0759
_refine_ls_wR_factor_gt          0.0749
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.01526(16) 0.76746(6) 0.21536(5) 0.0203(2) Uani 1 1 d . . .
O2 O 0.01985(16) 0.54475(6) 0.22259(4) 0.01485(19) Uani 1 1 d . . .
O3 O 0.62118(17) 0.69544(6) 0.47393(5) 0.0194(2) Uani 1 1 d . . .
O4 O -0.31406(16) 0.58808(6) 0.17284(5) 0.0195(2) Uani 1 1 d . . .
N1 N 0.24266(19) 0.67710(7) 0.15303(6) 0.0124(2) Uani 1 1 d . . .
H1N1 H 0.379(3) 0.6537(10) 0.1507(8) 0.015(4) Uiso 1 1 d . . .
C1 C 0.2097(2) 0.74214(8) 0.19980(6) 0.0118(2) Uani 1 1 d . . .
C2 C 0.4261(2) 0.78419(8) 0.22949(6) 0.0134(3) Uani 1 1 d . . .
H2A H 0.424(3) 0.8428(9) 0.2094(7) 0.010(3) Uiso 1 1 d . . .
H2B H 0.562(3) 0.7566(10) 0.2128(8) 0.015(4) Uiso 1 1 d . . .
C3 C 0.4290(2) 0.78894(8) 0.31125(6) 0.0124(3) Uani 1 1 d . . .
H3 H 0.276(3) 0.7978(9) 0.3281(8) 0.010(3) Uiso 1 1 d . . .
C4 C 0.5840(2) 0.86137(8) 0.34049(7) 0.0161(3) Uani 1 1 d . . .
H4A H 0.729(3) 0.8592(9) 0.3155(8) 0.014(3) Uiso 1 1 d . . .
H4B H 0.521(3) 0.9170(10) 0.3341(7) 0.012(3) Uiso 1 1 d . . .
C5 C 0.6152(3) 0.83788(8) 0.41958(7) 0.0192(3) Uani 1 1 d . . .
H5A H 0.495(3) 0.8607(11) 0.4481(9) 0.024(4) Uiso 1 1 d . . .
H5B H 0.757(3) 0.8586(11) 0.4428(9) 0.027(4) Uiso 1 1 d . . .
C6 C 0.5943(2) 0.74061(8) 0.42184(6) 0.0148(3) Uani 1 1 d . . .
C7 C 0.5315(2) 0.70841(8) 0.34738(6) 0.0132(3) Uani 1 1 d . . .
H7 H 0.685(3) 0.6982(10) 0.3234(8) 0.020(4) Uiso 1 1 d . . .
C8 C 0.3956(2) 0.62420(8) 0.34607(6) 0.0143(2) Uani 1 1 d . . .
H8A H 0.377(3) 0.6067(9) 0.2975(8) 0.014(3) Uiso 1 1 d . . .
H8B H 0.497(3) 0.5789(10) 0.3697(7) 0.013(3) Uiso 1 1 d . . .
C9 C 0.1667(2) 0.62794(8) 0.38416(6) 0.0142(3) Uani 1 1 d . . .
H9 H 0.143(3) 0.6760(9) 0.4133(8) 0.011(3) Uiso 1 1 d . . .
C10 C 0.0088(2) 0.56569(8) 0.38280(6) 0.0152(3) Uani 1 1 d . . .
H10 H -0.132(3) 0.5723(10) 0.4112(8) 0.020(4) Uiso 1 1 d . . .
C11 C 0.0278(2) 0.48321(8) 0.34053(7) 0.0160(3) Uani 1 1 d . . .
H11A H -0.031(3) 0.4355(11) 0.3670(8) 0.021(4) Uiso 1 1 d . . .
H11B H 0.192(3) 0.4698(10) 0.3315(8) 0.020(4) Uiso 1 1 d . . .
C12 C -0.1029(2) 0.48608(8) 0.27044(7) 0.0166(3) Uani 1 1 d . . .
H12A H -0.266(3) 0.5074(10) 0.2756(7) 0.014(3) Uiso 1 1 d . . .
H12B H -0.096(3) 0.4293(9) 0.2476(7) 0.009(3) Uiso 1 1 d . . .
C13 C -0.1058(2) 0.58872(8) 0.17539(6) 0.0132(3) Uani 1 1 d . . .
C14 C 0.0470(2) 0.63331(8) 0.12086(6) 0.0120(2) Uani 1 1 d . . .
H14 H -0.048(3) 0.6766(10) 0.0979(8) 0.015(4) Uiso 1 1 d . . .
C15 C 0.1330(2) 0.56535(8) 0.06653(6) 0.0140(3) Uani 1 1 d . . .
H15 H 0.236(3) 0.5272(9) 0.0939(8) 0.017(4) Uiso 1 1 d . . .
C16 C -0.0658(3) 0.51012(9) 0.03811(8) 0.0217(3) Uani 1 1 d . . .
H16A H -0.128(3) 0.4736(10) 0.0777(9) 0.025(4) Uiso 1 1 d . . .
H16B H -0.195(3) 0.5455(12) 0.0189(10) 0.034(5) Uiso 1 1 d . . .
H16C H -0.014(3) 0.4717(10) 0.0016(8) 0.024(4) Uiso 1 1 d . . .
C17 C 0.2705(3) 0.60666(9) 0.00569(7) 0.0198(3) Uani 1 1 d . . .
H17A H 0.405(3) 0.6378(11) 0.0243(9) 0.027(4) Uiso 1 1 d . . .
H17B H 0.323(3) 0.5607(10) -0.0251(9) 0.022(4) Uiso 1 1 d . . .
C18 C 0.1369(4) 0.66823(12) -0.04177(9) 0.0356(4) Uani 1 1 d . . .
H18A H 0.091(4) 0.7186(12) -0.0149(11) 0.044(5) Uiso 1 1 d . . .
H18B H 0.232(4) 0.6890(12) -0.0818(10) 0.037(5) Uiso 1 1 d . . .
H18C H -0.006(4) 0.6403(13) -0.0587(10) 0.042(5) 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 1.2273(16) . ?
O2 C13 1.3313(15) . ?
O2 C12 1.4598(15) . ?
O3 C6 1.2091(15) . ?
O4 C13 1.2069(17) . ?
N1 C1 1.3474(16) . ?
N1 C14 1.4513(15) . ?
N1 H1N1 0.869(17) . ?
C1 C2 1.5177(17) . ?
C2 C3 1.5306(16) . ?
C2 H2A 0.982(14) . ?
C2 H2B 0.948(17) . ?
C3 C7 1.5373(17) . ?
C3 C4 1.5372(17) . ?
C3 H3 0.949(16) . ?
C4 C5 1.5336(17) . ?
C4 H4A 0.962(17) . ?
C4 H4B 0.943(16) . ?
C5 C6 1.5118(18) . ?
C5 H5A 0.945(18) . ?
C5 H5B 0.985(19) . ?
C6 C7 1.5228(16) . ?
C7 C8 1.5232(17) . ?
C7 H7 1.009(17) . ?
C8 C9 1.5060(18) . ?
C8 H8A 0.953(15) . ?
C8 H8B 1.014(15) . ?
C9 C10 1.3289(19) . ?
C9 H9 0.933(15) . ?
C10 C11 1.5060(18) . ?
C10 H10 0.977(17) . ?
C11 C12 1.5138(18) . ?
C11 H11A 0.952(16) . ?
C11 H11B 0.986(18) . ?
C12 H12A 1.007(17) . ?
C12 H12B 0.978(14) . ?
C13 C14 1.5165(17) . ?
C14 C15 1.5453(16) . ?
C14 H14 0.966(16) . ?
C15 C17 1.5289(18) . ?
C15 C16 1.5297(18) . ?
C15 H15 0.985(16) . ?
C16 H16A 0.998(17) . ?
C16 H16B 0.99(2) . ?
C16 H16C 0.953(17) . ?
C17 C18 1.515(2) . ?
C17 H17A 0.980(19) . ?
C17 H17B 0.964(17) . ?
C18 H18A 0.965(19) . ?
C18 H18B 0.99(2) . ?
C18 H18C 0.99(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
C13 O2 C12 117.28(10) . . ?
C1 N1 C14 120.50(10) . . ?
C1 N1 H1N1 118.2(10) . . ?
C14 N1 H1N1 119.5(10) . . ?
O1 C1 N1 121.51(11) . . ?
O1 C1 C2 122.28(11) . . ?
N1 C1 C2 116.17(11) . . ?
C1 C2 C3 113.27(10) . . ?
C1 C2 H2A 104.2(9) . . ?
C3 C2 H2A 109.7(8) . . ?
C1 C2 H2B 111.8(9) . . ?
C3 C2 H2B 110.0(9) . . ?
H2A C2 H2B 107.6(13) . . ?
C2 C3 C7 113.85(10) . . ?
C2 C3 C4 113.37(10) . . ?
C7 C3 C4 102.13(10) . . ?
C2 C3 H3 109.2(9) . . ?
C7 C3 H3 109.3(9) . . ?
C4 C3 H3 108.7(9) . . ?
C5 C4 C3 103.80(10) . . ?
C5 C4 H4A 110.9(9) . . ?
C3 C4 H4A 108.2(9) . . ?
C5 C4 H4B 112.6(9) . . ?
C3 C4 H4B 113.4(9) . . ?
H4A C4 H4B 107.9(13) . . ?
C6 C5 C4 104.71(10) . . ?
C6 C5 H5A 107.3(10) . . ?
C4 C5 H5A 111.6(10) . . ?
C6 C5 H5B 112.3(10) . . ?
C4 C5 H5B 116.5(10) . . ?
H5A C5 H5B 104.2(13) . . ?
O3 C6 C5 126.06(11) . . ?
O3 C6 C7 125.29(11) . . ?
C5 C6 C7 108.65(10) . . ?
C8 C7 C6 114.74(10) . . ?
C8 C7 C3 119.20(11) . . ?
C6 C7 C3 103.21(9) . . ?
C8 C7 H7 108.3(9) . . ?
C6 C7 H7 104.3(9) . . ?
C3 C7 H7 105.8(9) . . ?
C9 C8 C7 114.47(11) . . ?
C9 C8 H8A 111.1(10) . . ?
C7 C8 H8A 108.5(9) . . ?
C9 C8 H8B 109.2(8) . . ?
C7 C8 H8B 106.6(8) . . ?
H8A C8 H8B 106.5(12) . . ?
C10 C9 C8 124.66(12) . . ?
C10 C9 H9 119.2(9) . . ?
C8 C9 H9 116.0(9) . . ?
C9 C10 C11 125.11(12) . . ?
C9 C10 H10 119.2(9) . . ?
C11 C10 H10 115.7(9) . . ?
C10 C11 C12 113.15(11) . . ?
C10 C11 H11A 111.1(9) . . ?
C12 C11 H11A 107.0(10) . . ?
C10 C11 H11B 109.8(9) . . ?
C12 C11 H11B 109.8(9) . . ?
H11A C11 H11B 105.6(14) . . ?
O2 C12 C11 107.79(11) . . ?
O2 C12 H12A 108.1(9) . . ?
C11 C12 H12A 113.4(8) . . ?
O2 C12 H12B 105.8(8) . . ?
C11 C12 H12B 109.4(8) . . ?
H12A C12 H12B 111.9(13) . . ?
O4 C13 O2 124.64(12) . . ?
O4 C13 C14 124.08(11) . . ?
O2 C13 C14 111.06(11) . . ?
N1 C14 C13 112.94(9) . . ?
N1 C14 C15 109.81(10) . . ?
C13 C14 C15 108.68(10) . . ?
N1 C14 H14 107.7(9) . . ?
C13 C14 H14 106.4(9) . . ?
C15 C14 H14 111.3(8) . . ?
C17 C15 C16 111.58(11) . . ?
C17 C15 C14 111.85(10) . . ?
C16 C15 C14 111.48(11) . . ?
C17 C15 H15 108.7(9) . . ?
C16 C15 H15 107.6(9) . . ?
C14 C15 H15 105.2(9) . . ?
C15 C16 H16A 109.2(10) . . ?
C15 C16 H16B 112.5(10) . . ?
H16A C16 H16B 108.1(15) . . ?
C15 C16 H16C 111.1(10) . . ?
H16A C16 H16C 106.9(13) . . ?
H16B C16 H16C 108.8(14) . . ?
C18 C17 C15 115.65(13) . . ?
C18 C17 H17A 107.7(10) . . ?
C15 C17 H17A 110.8(10) . . ?
C18 C17 H17B 106.0(10) . . ?
C15 C17 H17B 107.4(9) . . ?
H17A C17 H17B 109.0(14) . . ?
C17 C18 H18A 110.1(12) . . ?
C17 C18 H18B 111.3(12) . . ?
H18A C18 H18B 106.8(16) . . ?
C17 C18 H18C 109.9(12) . . ?
H18A C18 H18C 106.8(17) . . ?
H18B C18 H18C 111.8(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
N1 H1N1 O4 0.869(17) 2.090(17) 2.9374(14) 164.9(14) 1_655

_diffrn_measured_fraction_theta_max 0.890
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.041

