# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_4a
_database_code_depnum_ccdc_archive 'CCDC 962972'
_audit_update_record             
;
2013-09-24 deposited with the CCDC.
2014-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 N O3'
_chemical_formula_sum            'C13 H11 N O3'
_chemical_formula_weight         229.23

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   Pca2(1)
_symmetry_space_group_name_Hall  'P 2c -2ac'

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

_cell_length_a                   15.024(3)
_cell_length_b                   21.464(4)
_cell_length_c                   13.309(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4291.8(15)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4726
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      25.31

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.87
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1920
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   'SADABS v2009/1, Sheldrick, G.M., (2009)'

_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 APEX 2 CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            36812
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         0.95
_diffrn_reflns_theta_max         26.54
_reflns_number_total             8811
_reflns_number_gt                5081
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX 2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'

_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)+(0.0580P)²+2.9563P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   'geom except OH coords freely refined'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881; 4168 Friedel pairs'
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration unk
_refine_ls_number_reflns         8811
_refine_ls_number_parameters     625
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1218
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1684
_refine_ls_wR_factor_gt          0.1288
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
N1 N 0.2910(2) 0.41333(18) 0.0256(3) 0.0376(10) Uani 1 1 d . . .
O1 O 0.2659(2) 0.47652(13) 0.0243(3) 0.0397(8) Uani 1 1 d . . .
C1 C 0.1776(3) 0.4789(2) 0.0284(4) 0.0346(11) Uani 1 1 d . . .
C2 C 0.1423(3) 0.4208(2) 0.0347(4) 0.0360(11) Uani 1 1 d . . .
C3 C 0.0452(3) 0.4153(2) 0.0431(6) 0.076(2) Uani 1 1 d . . .
O2 O 0.0061(2) 0.36714(18) 0.0417(7) 0.188(4) Uani 1 1 d . . .
C4 C -0.0035(3) 0.4765(2) 0.0583(6) 0.073(2) Uani 1 1 d . . .
H4A H -0.0041 0.4863 0.1310 0.088 Uiso 1 1 calc R . .
H4B H -0.0660 0.4713 0.0365 0.088 Uiso 1 1 calc R . .
C5 C 0.0365(4) 0.5314(3) 0.0022(7) 0.087(2) Uani 1 1 d . . .
H5A H 0.0309 0.5244 -0.0710 0.105 Uiso 1 1 calc R . .
H5B H 0.0032 0.5698 0.0193 0.105 Uiso 1 1 calc R . .
C6 C 0.1324(3) 0.5401(2) 0.0284(4) 0.0474(13) Uani 1 1 d . . .
H6A H 0.1611 0.5680 -0.0212 0.057 Uiso 1 1 calc R . .
H6B H 0.1376 0.5595 0.0956 0.057 Uiso 1 1 calc R . .
C7 C 0.2180(3) 0.3797(2) 0.0311(4) 0.0312(11) Uani 1 1 d . . .
C8 C 0.2273(3) 0.3116(2) 0.0321(4) 0.0320(11) Uani 1 1 d . . .
C9 C 0.3104(3) 0.2828(2) 0.0219(4) 0.0383(12) Uani 1 1 d . . .
O3 O 0.3881(2) 0.31512(17) 0.0104(3) 0.0480(9) Uani 1 1 d . . .
H3 H 0.372(3) 0.361(2) 0.016(4) 0.072 Uiso 1 1 d . . .
C10 C 0.3176(3) 0.2181(2) 0.0210(4) 0.0448(13) Uani 1 1 d . . .
H10 H 0.3743 0.1993 0.0123 0.054 Uiso 1 1 calc R . .
C11 C 0.2445(4) 0.1816(2) 0.0326(4) 0.0505(13) Uani 1 1 d . . .
H11 H 0.2504 0.1376 0.0327 0.061 Uiso 1 1 calc R . .
C12 C 0.1611(3) 0.2086(2) 0.0442(4) 0.0479(13) Uani 1 1 d . . .
H12 H 0.1098 0.1831 0.0515 0.057 Uiso 1 1 calc R . .
C13 C 0.1530(3) 0.2722(2) 0.0451(4) 0.0382(11) Uani 1 1 d . . .
H13 H 0.0958 0.2903 0.0547 0.046 Uiso 1 1 calc R . .
N1A N 0.2043(2) 0.83657(18) 0.3024(3) 0.0388(10) Uani 1 1 d . . .
O1A O 0.2308(2) 0.77419(13) 0.3032(3) 0.0419(9) Uani 1 1 d . . .
C1A C 0.3198(3) 0.7726(2) 0.2997(4) 0.0396(12) Uani 1 1 d . . .
C2A C 0.3539(3) 0.8311(2) 0.2979(4) 0.0359(11) Uani 1 1 d . . .
C3A C 0.4512(3) 0.8378(3) 0.2968(5) 0.0569(15) Uani 1 1 d . . .
O2A O 0.4893(2) 0.88729(19) 0.2996(5) 0.1050(19) Uani 1 1 d . . .
C4A C 0.5021(4) 0.7777(3) 0.2858(6) 0.079(2) Uani 1 1 d . . .
H4C H 0.5081 0.7680 0.2134 0.095 Uiso 1 1 calc R . .
H4D H 0.5627 0.7837 0.3133 0.095 Uiso 1 1 calc R . .
C5A C 0.4605(4) 0.7234(3) 0.3369(5) 0.0707(17) Uani 1 1 d . . .
H5C H 0.4605 0.7306 0.4104 0.085 Uiso 1 1 calc R . .
H5D H 0.4966 0.6857 0.3235 0.085 Uiso 1 1 calc R . .
C6A C 0.3650(3) 0.7120(2) 0.3017(4) 0.0536(14) Uani 1 1 d . . .
H6C H 0.3650 0.6932 0.2338 0.064 Uiso 1 1 calc R . .
H6D H 0.3342 0.6833 0.3484 0.064 Uiso 1 1 calc R . .
C7A C 0.2767(3) 0.8712(2) 0.3003(4) 0.0335(11) Uani 1 1 d . . .
C8A C 0.2650(3) 0.93951(19) 0.3015(4) 0.0330(11) Uani 1 1 d . . .
C9A C 0.1800(3) 0.9665(2) 0.3139(4) 0.0396(12) Uani 1 1 d . . .
O3A O 0.1039(2) 0.93322(17) 0.3238(3) 0.0502(10) Uani 1 1 d . . .
H3A H 0.112(3) 0.892(2) 0.330(4) 0.075 Uiso 1 1 d . . .
C10A C 0.1707(4) 1.0305(2) 0.3151(4) 0.0513(14) Uani 1 1 d . . .
H10A H 0.1135 1.0486 0.3234 0.062 Uiso 1 1 calc R . .
C11A C 0.2452(4) 1.0686(2) 0.3039(5) 0.0528(13) Uani 1 1 d . . .
H11A H 0.2384 1.1126 0.3042 0.063 Uiso 1 1 calc R . .
C12A C 0.3279(4) 1.0431(2) 0.2926(4) 0.0497(14) Uani 1 1 d . . .
H12A H 0.3786 1.0691 0.2846 0.060 Uiso 1 1 calc R . .
C13A C 0.3372(3) 0.9793(2) 0.2930(4) 0.0408(12) Uani 1 1 d . . .
H13A H 0.3952 0.9619 0.2872 0.049 Uiso 1 1 calc R . .
N1B N 0.7083(2) 0.07764(18) 0.5490(3) 0.0387(10) Uani 1 1 d . . .
O1B O 0.7465(2) 0.01777(12) 0.5517(3) 0.0424(8) Uani 1 1 d . . .
C1B C 0.8349(3) 0.0249(2) 0.5552(4) 0.0382(11) Uani 1 1 d . . .
C2B C 0.8578(3) 0.0860(2) 0.5567(4) 0.0346(10) Uani 1 1 d . . .
C3B C 0.9527(3) 0.1026(2) 0.5605(4) 0.0494(13) Uani 1 1 d . . .
O2B O 0.9811(2) 0.15573(16) 0.5642(4) 0.0859(15) Uani 1 1 d . . .
C4B C 1.0150(4) 0.0478(3) 0.5556(5) 0.0742(18) Uani 1 1 d . . .
H4E H 1.0327 0.0419 0.4845 0.089 Uiso 1 1 calc R . .
H4F H 1.0694 0.0586 0.5936 0.089 Uiso 1 1 calc R . .
C5B C 0.9834(4) -0.0101(3) 0.5921(7) 0.098(2) Uani 1 1 d . . .
H5E H 0.9843 -0.0083 0.6665 0.117 Uiso 1 1 calc R . .
H5F H 1.0264 -0.0426 0.5716 0.117 Uiso 1 1 calc R . .
C6B C 0.8930(3) -0.0307(2) 0.5605(4) 0.0497(13) Uani 1 1 d . . .
H6E H 0.8960 -0.0512 0.4939 0.060 Uiso 1 1 calc R . .
H6F H 0.8688 -0.0610 0.6096 0.060 Uiso 1 1 calc R . .
C7B C 0.7736(3) 0.11867(19) 0.5524(4) 0.0306(11) Uani 1 1 d . . .
C8B C 0.7492(3) 0.18511(18) 0.5494(4) 0.0351(11) Uani 1 1 d . . .
C9B C 0.6614(3) 0.2047(2) 0.5337(4) 0.0416(12) Uani 1 1 d . . .
O3B O 0.5915(2) 0.16417(17) 0.5249(3) 0.0537(10) Uani 1 1 d . . .
H3B H 0.621(3) 0.125(2) 0.530(4) 0.081 Uiso 1 1 d . . .
C10B C 0.6402(4) 0.2670(2) 0.5298(4) 0.0524(14) Uani 1 1 d . . .
H10B H 0.5802 0.2793 0.5195 0.063 Uiso 1 1 calc R . .
C11B C 0.7051(4) 0.3116(2) 0.5406(4) 0.0560(15) Uani 1 1 d . . .
H11B H 0.6902 0.3545 0.5356 0.067 Uiso 1 1 calc R . .
C12B C 0.7924(4) 0.2938(2) 0.5588(4) 0.0528(14) Uani 1 1 d . . .
H12B H 0.8369 0.3246 0.5688 0.063 Uiso 1 1 calc R . .
C13B C 0.8147(3) 0.2313(2) 0.5623(4) 0.0447(13) Uani 1 1 d . . .
H13B H 0.8748 0.2194 0.5735 0.054 Uiso 1 1 calc R . .
N1C N 0.2906(2) 0.33046(19) 0.7855(3) 0.0353(10) Uani 1 1 d . . .
O1C O 0.2566(3) 0.26938(13) 0.7860(3) 0.0390(8) Uani 1 1 d . . .
C1C C 0.1684(3) 0.2730(2) 0.7748(3) 0.0327(11) Uani 1 1 d . . .
C2C C 0.1414(3) 0.3328(2) 0.7669(3) 0.0311(11) Uani 1 1 d . . .
C3C C 0.0467(3) 0.3452(2) 0.7462(4) 0.0473(13) Uani 1 1 d . . .
O2C O 0.0157(2) 0.39672(17) 0.7295(4) 0.0722(11) Uani 1 1 d . . .
C4C C -0.0109(3) 0.2889(3) 0.7367(5) 0.0622(15) Uani 1 1 d . . .
H4G H -0.0108 0.2752 0.6658 0.075 Uiso 1 1 calc R . .
H4H H -0.0727 0.3004 0.7545 0.075 Uiso 1 1 calc R . .
C5C C 0.0192(3) 0.2328(2) 0.8050(5) 0.0641(15) Uani 1 1 d . . .
H5G H 0.0163 0.2451 0.8767 0.077 Uiso 1 1 calc R . .
H5H H -0.0209 0.1968 0.7946 0.077 Uiso 1 1 calc R . .
C6C C 0.1147(3) 0.2150(2) 0.7771(4) 0.0459(13) Uani 1 1 d . . .
H6G H 0.1393 0.1857 0.8274 0.055 Uiso 1 1 calc R . .
H6H H 0.1159 0.1945 0.7105 0.055 Uiso 1 1 calc R . .
C7C C 0.2227(3) 0.3688(2) 0.7756(3) 0.0303(11) Uani 1 1 d . . .
C8C C 0.2415(4) 0.4358(2) 0.7762(4) 0.0361(12) Uani 1 1 d . . .
C9C C 0.3287(4) 0.4586(2) 0.7911(4) 0.0437(13) Uani 1 1 d . . .
O3C O 0.4013(2) 0.42140(18) 0.8017(3) 0.0569(11) Uani 1 1 d . . .
H3C H 0.382(4) 0.382(3) 0.814(5) 0.085 Uiso 1 1 d . . .
C10C C 0.3439(4) 0.5218(3) 0.7965(5) 0.0586(15) Uani 1 1 d . . .
H10C H 0.4025 0.5367 0.8091 0.070 Uiso 1 1 calc R . .
C11C C 0.2758(5) 0.5637(3) 0.7840(5) 0.0649(19) Uani 1 1 d . . .
H11C H 0.2878 0.6072 0.7864 0.078 Uiso 1 1 calc R . .
C12C C 0.1905(5) 0.5432(3) 0.7680(4) 0.0562(16) Uani 1 1 d . . .
H12C H 0.1433 0.5721 0.7589 0.067 Uiso 1 1 calc R . .
C13C C 0.1741(4) 0.4797(2) 0.7653(4) 0.0456(14) Uani 1 1 d . . .
H13C H 0.1148 0.4657 0.7557 0.055 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.316(5) . ?
N1 O1 1.408(5) . ?
O1 C1 1.330(5) . ?
C1 C2 1.358(6) . ?
C1 C6 1.477(6) . ?
C2 C7 1.440(6) . ?
C2 C3 1.469(7) . ?
C3 O2 1.189(6) . ?
C3 C4 1.518(7) . ?
C4 C5 1.519(9) . ?
C5 C6 1.494(7) . ?
C7 C8 1.467(6) . ?
C8 C9 1.400(6) . ?
C8 C13 1.412(6) . ?
C9 O3 1.368(5) . ?
C9 C10 1.392(6) . ?
C10 C11 1.357(7) . ?
C11 C12 1.389(7) . ?
C12 C13 1.371(6) . ?
N1A C7A 1.318(5) . ?
N1A O1A 1.397(5) . ?
O1A C1A 1.338(6) . ?
C1A C2A 1.357(6) . ?
C1A C6A 1.467(6) . ?
C2A C7A 1.445(6) . ?
C2A C3A 1.469(7) . ?
C3A O2A 1.207(6) . ?
C3A C4A 1.508(7) . ?
C4A C5A 1.487(8) . ?
C5A C6A 1.529(7) . ?
C7A C8A 1.477(6) . ?
C8A C13A 1.386(6) . ?
C8A C9A 1.411(7) . ?
C9A O3A 1.356(6) . ?
C9A C10A 1.381(7) . ?
C10A C11A 1.394(8) . ?
C11A C12A 1.366(8) . ?
C12A C13A 1.376(6) . ?
N1B C7B 1.319(5) . ?
N1B O1B 1.408(4) . ?
O1B C1B 1.338(6) . ?
C1B C2B 1.357(6) . ?
C1B C6B 1.480(6) . ?
C2B C7B 1.448(6) . ?
C2B C3B 1.470(7) . ?
C3B O2B 1.219(6) . ?
C3B C4B 1.504(7) . ?
C4B C5B 1.416(7) . ?
C5B C6B 1.490(7) . ?
C7B C8B 1.473(6) . ?
C8B C9B 1.400(7) . ?
C8B C13B 1.407(6) . ?
C9B O3B 1.369(6) . ?
C9B C10B 1.376(6) . ?
C10B C11B 1.374(7) . ?
C11B C12B 1.387(7) . ?
C12B C13B 1.384(6) . ?
N1C C7C 1.317(5) . ?
N1C O1C 1.407(5) . ?
O1C C1C 1.337(6) . ?
C1C C2C 1.350(6) . ?
C1C C6C 1.484(6) . ?
C2C C7C 1.449(6) . ?
C2C C3C 1.474(7) . ?
C3C O2C 1.219(6) . ?
C3C C4C 1.492(7) . ?
C4C C5C 1.575(7) . ?
C5C C6C 1.531(7) . ?
C7C C8C 1.467(6) . ?
C8C C13C 1.390(7) . ?
C8C C9C 1.412(7) . ?
C9C O3C 1.358(6) . ?
C9C C10C 1.379(7) . ?
C10C C11C 1.372(8) . ?
C11C C12C 1.372(8) . ?
C12C C13C 1.385(7) . ?

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
C7 N1 O1 107.9(3) . . ?
C1 O1 N1 107.7(3) . . ?
O1 C1 C2 110.9(4) . . ?
O1 C1 C6 119.5(4) . . ?
C2 C1 C6 129.6(4) . . ?
C1 C2 C7 104.7(4) . . ?
C1 C2 C3 117.8(4) . . ?
C7 C2 C3 137.5(4) . . ?
O2 C3 C2 124.0(5) . . ?
O2 C3 C4 121.1(5) . . ?
C2 C3 C4 114.8(4) . . ?
C3 C4 C5 114.5(5) . . ?
C6 C5 C4 111.3(5) . . ?
C1 C6 C5 109.4(4) . . ?
N1 C7 C2 108.8(4) . . ?
N1 C7 C8 117.9(4) . . ?
C2 C7 C8 133.3(4) . . ?
C9 C8 C13 116.9(4) . . ?
C9 C8 C7 121.7(4) . . ?
C13 C8 C7 121.5(4) . . ?
O3 C9 C10 116.0(4) . . ?
O3 C9 C8 123.2(4) . . ?
C10 C9 C8 120.8(4) . . ?
C11 C10 C9 120.8(5) . . ?
C10 C11 C12 120.1(4) . . ?
C13 C12 C11 119.8(5) . . ?
C12 C13 C8 121.7(4) . . ?
C7A N1A O1A 107.8(3) . . ?
C1A O1A N1A 108.0(3) . . ?
O1A C1A C2A 110.7(4) . . ?
O1A C1A C6A 119.0(4) . . ?
C2A C1A C6A 130.2(5) . . ?
C1A C2A C7A 104.4(4) . . ?
C1A C2A C3A 117.9(4) . . ?
C7A C2A C3A 137.7(4) . . ?
O2A C3A C2A 124.0(5) . . ?
O2A C3A C4A 121.0(5) . . ?
C2A C3A C4A 114.9(5) . . ?
C5A C4A C3A 114.4(5) . . ?
C4A C5A C6A 112.2(5) . . ?
C1A C6A C5A 107.4(4) . . ?
N1A C7A C2A 109.1(4) . . ?
N1A C7A C8A 117.5(4) . . ?
C2A C7A C8A 133.5(4) . . ?
C13A C8A C9A 117.7(4) . . ?
C13A C8A C7A 121.2(4) . . ?
C9A C8A C7A 121.1(4) . . ?
O3A C9A C10A 115.9(4) . . ?
O3A C9A C8A 124.0(4) . . ?
C10A C9A C8A 120.1(5) . . ?
C9A C10A C11A 120.0(5) . . ?
C12A C11A C10A 120.5(4) . . ?
C11A C12A C13A 119.3(5) . . ?
C12A C13A C8A 122.3(5) . . ?
C7B N1B O1B 107.8(3) . . ?
C1B O1B N1B 107.5(3) . . ?
O1B C1B C2B 111.3(4) . . ?
O1B C1B C6B 119.7(4) . . ?
C2B C1B C6B 129.0(4) . . ?
C1B C2B C7B 104.2(4) . . ?
C1B C2B C3B 118.7(4) . . ?
C7B C2B C3B 137.0(4) . . ?
O2B C3B C2B 124.5(4) . . ?
O2B C3B C4B 121.1(4) . . ?
C2B C3B C4B 114.4(4) . . ?
C5B C4B C3B 117.5(5) . . ?
C4B C5B C6B 118.0(6) . . ?
C1B C6B C5B 108.1(4) . . ?
N1B C7B C2B 109.1(4) . . ?
N1B C7B C8B 117.4(4) . . ?
C2B C7B C8B 133.4(4) . . ?
C9B C8B C13B 117.8(4) . . ?
C9B C8B C7B 121.9(4) . . ?
C13B C8B C7B 120.3(4) . . ?
O3B C9B C10B 115.9(4) . . ?
O3B C9B C8B 123.1(4) . . ?
C10B C9B C8B 121.0(5) . . ?
C11B C10B C9B 120.6(5) . . ?
C10B C11B C12B 119.8(5) . . ?
C13B C12B C11B 120.1(5) . . ?
C12B C13B C8B 120.6(5) . . ?
C7C N1C O1C 107.6(4) . . ?
C1C O1C N1C 107.8(3) . . ?
O1C C1C C2C 111.2(4) . . ?
O1C C1C C6C 119.2(4) . . ?
C2C C1C C6C 129.6(5) . . ?
C1C C2C C7C 104.3(4) . . ?
C1C C2C C3C 118.4(4) . . ?
C7C C2C C3C 137.1(4) . . ?
O2C C3C C2C 124.5(5) . . ?
O2C C3C C4C 119.8(5) . . ?
C2C C3C C4C 115.4(4) . . ?
C3C C4C C5C 113.8(5) . . ?
C6C C5C C4C 108.7(4) . . ?
C1C C6C C5C 107.7(4) . . ?
N1C C7C C2C 109.1(4) . . ?
N1C C7C C8C 117.6(4) . . ?
C2C C7C C8C 133.2(4) . . ?
C13C C8C C9C 117.1(5) . . ?
C13C C8C C7C 121.7(5) . . ?
C9C C8C C7C 121.2(5) . . ?
O3C C9C C10C 116.1(5) . . ?
O3C C9C C8C 123.8(5) . . ?
C10C C9C C8C 120.1(5) . . ?
C11C C10C C9C 121.0(6) . . ?
C12C C11C C10C 120.3(5) . . ?
C11C C12C C13C 119.1(6) . . ?
C12C C13C C8C 122.3(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
C7 N1 O1 C1 -0.5(5) . . . . ?
N1 O1 C1 C2 1.4(6) . . . . ?
N1 O1 C1 C6 179.9(4) . . . . ?
O1 C1 C2 C7 -1.7(6) . . . . ?
C6 C1 C2 C7 -180.0(5) . . . . ?
O1 C1 C2 C3 178.1(5) . . . . ?
C6 C1 C2 C3 -0.2(9) . . . . ?
C1 C2 C3 O2 174.3(8) . . . . ?
C7 C2 C3 O2 -6.1(14) . . . . ?
C1 C2 C3 C4 -8.1(9) . . . . ?
C7 C2 C3 C4 171.5(6) . . . . ?
O2 C3 C4 C5 -146.3(9) . . . . ?
C2 C3 C4 C5 36.1(9) . . . . ?
C3 C4 C5 C6 -55.8(8) . . . . ?
O1 C1 C6 C5 163.0(5) . . . . ?
C2 C1 C6 C5 -18.8(8) . . . . ?
C4 C5 C6 C1 44.3(7) . . . . ?
O1 N1 C7 C2 -0.5(5) . . . . ?
O1 N1 C7 C8 179.2(4) . . . . ?
C1 C2 C7 N1 1.3(6) . . . . ?
C3 C2 C7 N1 -178.3(7) . . . . ?
C1 C2 C7 C8 -178.4(5) . . . . ?
C3 C2 C7 C8 2.0(12) . . . . ?
N1 C7 C8 C9 -3.5(7) . . . . ?
C2 C7 C8 C9 176.2(5) . . . . ?
N1 C7 C8 C13 175.4(4) . . . . ?
C2 C7 C8 C13 -4.9(9) . . . . ?
C13 C8 C9 O3 -178.9(5) . . . . ?
C7 C8 C9 O3 0.0(8) . . . . ?
C13 C8 C9 C10 2.3(8) . . . . ?
C7 C8 C9 C10 -178.8(5) . . . . ?
O3 C9 C10 C11 179.5(5) . . . . ?
C8 C9 C10 C11 -1.6(9) . . . . ?
C9 C10 C11 C12 0.8(9) . . . . ?
C10 C11 C12 C13 -0.7(9) . . . . ?
C11 C12 C13 C8 1.5(9) . . . . ?
C9 C8 C13 C12 -2.3(8) . . . . ?
C7 C8 C13 C12 178.8(5) . . . . ?
C7A N1A O1A C1A -1.1(6) . . . . ?
N1A O1A C1A C2A 0.8(6) . . . . ?
N1A O1A C1A C6A 178.8(5) . . . . ?
O1A C1A C2A C7A -0.2(6) . . . . ?
C6A C1A C2A C7A -177.9(6) . . . . ?
O1A C1A C2A C3A 178.4(5) . . . . ?
C6A C1A C2A C3A 0.7(9) . . . . ?
C1A C2A C3A O2A -176.7(7) . . . . ?
C7A C2A C3A O2A 1.3(12) . . . . ?
C1A C2A C3A C4A 6.7(9) . . . . ?
C7A C2A C3A C4A -175.3(6) . . . . ?
O2A C3A C4A C5A 148.0(7) . . . . ?
C2A C3A C4A C5A -35.2(9) . . . . ?
C3A C4A C5A C6A 56.4(8) . . . . ?
O1A C1A C6A C5A -158.7(5) . . . . ?
C2A C1A C6A C5A 18.8(8) . . . . ?
C4A C5A C6A C1A -45.3(7) . . . . ?
O1A N1A C7A C2A 1.0(5) . . . . ?
O1A N1A C7A C8A -178.6(5) . . . . ?
C1A C2A C7A N1A -0.5(6) . . . . ?
C3A C2A C7A N1A -178.6(6) . . . . ?
C1A C2A C7A C8A 179.0(6) . . . . ?
C3A C2A C7A C8A 0.8(12) . . . . ?
N1A C7A C8A C13A -175.9(5) . . . . ?
C2A C7A C8A C13A 4.7(10) . . . . ?
N1A C7A C8A C9A 5.8(8) . . . . ?
C2A C7A C8A C9A -173.6(5) . . . . ?
C13A C8A C9A O3A -179.6(5) . . . . ?
C7A C8A C9A O3A -1.2(8) . . . . ?
C13A C8A C9A C10A 1.4(8) . . . . ?
C7A C8A C9A C10A 179.8(5) . . . . ?
O3A C9A C10A C11A -179.1(5) . . . . ?
C8A C9A C10A C11A 0.0(8) . . . . ?
C9A C10A C11A C12A -0.5(9) . . . . ?
C10A C11A C12A C13A -0.4(9) . . . . ?
C11A C12A C13A C8A 2.0(9) . . . . ?
C9A C8A C13A C12A -2.4(9) . . . . ?
C7A C8A C13A C12A 179.2(5) . . . . ?
C7B N1B O1B C1B -0.9(6) . . . . ?
N1B O1B C1B C2B 1.0(6) . . . . ?
N1B O1B C1B C6B 178.9(4) . . . . ?
O1B C1B C2B C7B -0.8(6) . . . . ?
C6B C1B C2B C7B -178.4(5) . . . . ?
O1B C1B C2B C3B -179.9(5) . . . . ?
C6B C1B C2B C3B 2.4(9) . . . . ?
C1B C2B C3B O2B -178.4(6) . . . . ?
C7B C2B C3B O2B 2.8(11) . . . . ?
C1B C2B C3B C4B 3.7(8) . . . . ?
C7B C2B C3B C4B -175.1(6) . . . . ?
O2B C3B C4B C5B 154.5(7) . . . . ?
C2B C3B C4B C5B -27.5(9) . . . . ?
C3B C4B C5B C6B 46.5(10) . . . . ?
O1B C1B C6B C5B -164.3(6) . . . . ?
C2B C1B C6B C5B 13.1(8) . . . . ?
C4B C5B C6B C1B -36.8(9) . . . . ?
O1B N1B C7B C2B 0.4(6) . . . . ?
O1B N1B C7B C8B 179.4(4) . . . . ?
C1B C2B C7B N1B 0.2(6) . . . . ?
C3B C2B C7B N1B 179.1(6) . . . . ?
C1B C2B C7B C8B -178.6(6) . . . . ?
C3B C2B C7B C8B 0.4(11) . . . . ?
N1B C7B C8B C9B -6.1(8) . . . . ?
C2B C7B C8B C9B 172.6(5) . . . . ?
N1B C7B C8B C13B 173.9(5) . . . . ?
C2B C7B C8B C13B -7.4(9) . . . . ?
C13B C8B C9B O3B -176.9(5) . . . . ?
C7B C8B C9B O3B 3.2(8) . . . . ?
C13B C8B C9B C10B 0.9(8) . . . . ?
C7B C8B C9B C10B -179.1(5) . . . . ?
O3B C9B C10B C11B 178.3(5) . . . . ?
C8B C9B C10B C11B 0.4(9) . . . . ?
C9B C10B C11B C12B -2.0(9) . . . . ?
C10B C11B C12B C13B 2.4(8) . . . . ?
C11B C12B C13B C8B -1.2(8) . . . . ?
C9B C8B C13B C12B -0.4(8) . . . . ?
C7B C8B C13B C12B 179.5(5) . . . . ?
C7C N1C O1C C1C 0.9(5) . . . . ?
N1C O1C C1C C2C 0.0(5) . . . . ?
N1C O1C C1C C6C -177.4(4) . . . . ?
O1C C1C C2C C7C -0.8(5) . . . . ?
C6C C1C C2C C7C 176.3(5) . . . . ?
O1C C1C C2C C3C 175.3(4) . . . . ?
C6C C1C C2C C3C -7.7(8) . . . . ?
C1C C2C C3C O2C -173.9(5) . . . . ?
C7C C2C C3C O2C 0.5(9) . . . . ?
C1C C2C C3C C4C 0.5(7) . . . . ?
C7C C2C C3C C4C 174.8(6) . . . . ?
O2C C3C C4C C5C -152.9(5) . . . . ?
C2C C3C C4C C5C 32.4(7) . . . . ?
C3C C4C C5C C6C -58.7(7) . . . . ?
O1C C1C C6C C5C 157.7(5) . . . . ?
C2C C1C C6C C5C -19.2(7) . . . . ?
C4C C5C C6C C1C 48.7(6) . . . . ?
O1C N1C C7C C2C -1.4(5) . . . . ?
O1C N1C C7C C8C 178.2(4) . . . . ?
C1C C2C C7C N1C 1.3(5) . . . . ?
C3C C2C C7C N1C -173.5(5) . . . . ?
C1C C2C C7C C8C -178.1(5) . . . . ?
C3C C2C C7C C8C 7.0(10) . . . . ?
N1C C7C C8C C13C 179.4(4) . . . . ?
C2C C7C C8C C13C -1.2(9) . . . . ?
N1C C7C C8C C9C -2.7(7) . . . . ?
C2C C7C C8C C9C 176.7(5) . . . . ?
C13C C8C C9C O3C -179.2(5) . . . . ?
C7C C8C C9C O3C 2.8(8) . . . . ?
C13C C8C C9C C10C 1.3(8) . . . . ?
C7C C8C C9C C10C -176.6(5) . . . . ?
O3C C9C C10C C11C 178.1(6) . . . . ?
C8C C9C C10C C11C -2.3(10) . . . . ?
C9C C10C C11C C12C 1.5(10) . . . . ?
C10C C11C C12C C13C 0.4(9) . . . . ?
C11C C12C C13C C8C -1.4(9) . . . . ?
C9C C8C C13C C12C 0.5(8) . . . . ?
C7C C8C C13C C12C 178.5(5) . . . . ?

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
O3 H3 N1 1.02(5) 1.66(5) 2.572(5) 147(4) .
O3A H3A N1A 0.90(5) 1.86(5) 2.581(5) 135(5) .
O3B H3B N1B 0.95(5) 1.68(5) 2.576(5) 156(5) .
O3C H3C N1C 0.91(6) 1.80(6) 2.573(5) 141(6) .

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.54
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.051

_iucr_refine_instruction_details 
;
TITL 4a in Pca2(1)
CELL 0.71073  15.024  21.464  13.309  90.000  90.000  90.000
ZERR   16.00   0.003   0.004   0.003   0.000   0.000   0.000
LATT -1
SYMM -X, -Y, 0.5+Z
SYMM 0.5+X, -Y, Z
SYMM 0.5-X, Y, 0.5+Z
SFAC C H N O
UNIT 208 176 16 48
TEMP -123
SIZE 0.10 0.25 0.87
 
ACTA
CONF
WPDB -1
 
OMIT -3 54
OMIT 0 0 -2
L.S. 8
BOND
FMAP 2
PLAN 10
HTAB O3 N1
HTAB O3A N1A
HTAB O3B N1B
HTAB O3C N1C
 
REM   EXTI    0.000000  insig.
WGHT    0.058000    2.956300
FVAR       0.02799
N1    3    0.290992    0.413332    0.025561    11.00000    0.04034    0.04113 =
         0.03145    0.00071   -0.00015   -0.00221
O1    4    0.265936    0.476522    0.024336    11.00000    0.04193    0.04027 =
         0.03680    0.00250   -0.00075   -0.00546
C1    1    0.177575    0.478918    0.028450    11.00000    0.03975    0.04308 =
         0.02104   -0.00272   -0.00239    0.00036
C2    1    0.142335    0.420807    0.034668    11.00000    0.03688    0.03621 =
         0.03477   -0.00730   -0.00589    0.00484
C3    1    0.045182    0.415297    0.043079    11.00000    0.03484    0.04545 =
         0.14821   -0.01774    0.00375    0.00203
O2    4    0.006125    0.367139    0.041674    11.00000    0.03194    0.04656 =
         0.48653   -0.04989    0.00181   -0.01105
C4    1   -0.003500    0.476538    0.058343    11.00000    0.03594    0.05590 =
         0.12764    0.00602    0.00490    0.01176
AFIX  23
H4A   2   -0.004149    0.486337    0.131028    11.00000   -1.20000
H4B   2   -0.066036    0.471294    0.036475    11.00000   -1.20000
AFIX   0
C5    1    0.036537    0.531422    0.002239    11.00000    0.06508    0.05363 =
         0.14254   -0.02431   -0.01912    0.01532
AFIX  23
H5A   2    0.030864    0.524384   -0.070997    11.00000   -1.20000
H5B   2    0.003172    0.569766    0.019287    11.00000   -1.20000
AFIX   0
C6    1    0.132432    0.540071    0.028412    11.00000    0.06041    0.03610 =
         0.04581   -0.00377   -0.00933    0.00365
AFIX  23
H6A   2    0.161054    0.567991   -0.021205    11.00000   -1.20000
H6B   2    0.137593    0.559533    0.095600    11.00000   -1.20000
AFIX   0
C7    1    0.217969    0.379659    0.031133    11.00000    0.03245    0.04220 =
         0.01880   -0.00155   -0.00438   -0.00245
C8    1    0.227297    0.311645    0.032107    11.00000    0.04055    0.03665 =
         0.01879   -0.00412   -0.00378    0.00314
C9    1    0.310374    0.282751    0.021868    11.00000    0.03672    0.05699 =
         0.02118   -0.00131   -0.00212    0.00261
O3    4    0.388133    0.315120    0.010378    11.00000    0.03146    0.06182 =
         0.05074    0.00359    0.00125    0.00513
H3    2    0.371821    0.361097    0.015509    11.00000   -1.50000
C10   1    0.317577    0.218120    0.021045    11.00000    0.05048    0.05192 =
         0.03192   -0.00069   -0.00348    0.01172
AFIX  43
H10   2    0.374291    0.199315    0.012296    11.00000   -1.20000
AFIX   0
C11   1    0.244508    0.181640    0.032598    11.00000    0.07253    0.04100 =
         0.03784   -0.00210   -0.00310    0.01085
AFIX  43
H11   2    0.250420    0.137574    0.032729    11.00000   -1.20000
AFIX   0
C12   1    0.161074    0.208612    0.044233    11.00000    0.05634    0.04008 =
         0.04716   -0.00354    0.00091   -0.00497
AFIX  43
H12   2    0.109845    0.183066    0.051545    11.00000   -1.20000
AFIX   0
C13   1    0.152952    0.272234    0.045122    11.00000    0.03698    0.04127 =
         0.03643   -0.00519    0.00317   -0.00367
AFIX  43
H13   2    0.095834    0.290260    0.054743    11.00000   -1.20000
AFIX   0
N1A   3    0.204288    0.836567    0.302414    11.00000    0.03751    0.03674 =
         0.04212    0.00417   -0.00377   -0.00771
O1A   4    0.230775    0.774189    0.303235    11.00000    0.04820    0.03461 =
         0.04293    0.00336   -0.00866   -0.00891
C1A   1    0.319764    0.772572    0.299700    11.00000    0.04453    0.03932 =
         0.03503   -0.00458   -0.00965    0.00006
C2A   1    0.353871    0.831085    0.297940    11.00000    0.03363    0.03831 =
         0.03561   -0.00617   -0.00538   -0.00256
C3A   1    0.451172    0.837844    0.296820    11.00000    0.03911    0.05657 =
         0.07496   -0.00699   -0.00564    0.00071
O2A   4    0.489333    0.887295    0.299556    11.00000    0.03099    0.06554 =
         0.21835   -0.01336    0.00126   -0.01342
C4A   1    0.502098    0.777673    0.285828    11.00000    0.04531    0.06717 =
         0.12404   -0.02328    0.00214    0.02049
AFIX  23
H4C  2    0.508117    0.768029    0.213404    11.00000   -1.20000
H4D  2    0.562744    0.783667    0.313268    11.00000   -1.20000
AFIX   0
C5A   1    0.460508    0.723371    0.336936    11.00000    0.07072    0.06145 =
         0.07979   -0.00203   -0.00729    0.03455
AFIX  23
H5C  2    0.460510    0.730640    0.410392    11.00000   -1.20000
H5D  2    0.496569    0.685674    0.323519    11.00000   -1.20000
AFIX   0
C6A   1    0.365031    0.712039    0.301690    11.00000    0.07293    0.03862 =
         0.04935   -0.00657   -0.00831    0.00868
AFIX  23
H6C  2    0.364989    0.693165    0.233817    11.00000   -1.20000
H6D  2    0.334192    0.683329    0.348353    11.00000   -1.20000
AFIX   0
C7A   1    0.276691    0.871206    0.300301    11.00000    0.03409    0.03792 =
         0.02864    0.00128   -0.00080   -0.00367
C8A   1    0.264955    0.939513    0.301501    11.00000    0.03503    0.03321 =
         0.03084    0.00111    0.00207    0.00089
C9A   1    0.180041    0.966492    0.313946    11.00000    0.04472    0.04601 =
         0.02816    0.00464    0.00047    0.00637
O3A   4    0.103858    0.933215    0.323806    11.00000    0.03630    0.06355 =
         0.05089    0.00892    0.00053    0.00792
H3A   2    0.111859    0.891654    0.330378    11.00000   -1.50000
C10A  1    0.170718    1.030487    0.315065    11.00000    0.06204    0.05309 =
         0.03864   -0.00230   -0.00005    0.02427
AFIX  43
H10A  2    0.113489    1.048579    0.323436    11.00000   -1.20000
AFIX   0
C11A  1    0.245239    1.068566    0.303916    11.00000    0.08400    0.03575 =
         0.03878   -0.00447    0.00079    0.00851
AFIX  43
H11A  2    0.238445    1.112570    0.304175    11.00000   -1.20000
AFIX   0
C12A  1    0.327940    1.043089    0.292624    11.00000    0.07210    0.03804 =
         0.03885   -0.00359    0.00232   -0.00560
AFIX  43
H12A  2    0.378560    1.069142    0.284589    11.00000   -1.20000
AFIX   0
C13A  1    0.337212    0.979297    0.293002    11.00000    0.04756    0.03997 =
         0.03474   -0.00119    0.00446   -0.00374
AFIX  43
H13A  2    0.395152    0.961936    0.287238    11.00000   -1.20000
AFIX   0
N1B   3    0.708306    0.077642    0.549047    11.00000    0.03862    0.03904 =
         0.03855   -0.00149   -0.00298    0.00007
O1B   4    0.746482    0.017768    0.551721    11.00000    0.04661    0.03482 =
         0.04580    0.00085   -0.00267   -0.00297
C1B   1    0.834898    0.024872    0.555213    11.00000    0.04105    0.04518 =
         0.02822   -0.00180    0.00274   -0.00185
C2B   1    0.857827    0.085994    0.556731    11.00000    0.03574    0.03922 =
         0.02885    0.00260    0.00109   -0.00002
C3B   1    0.952729    0.102556    0.560463    11.00000    0.03447    0.04489 =
         0.06890    0.00608   -0.00600    0.00497
O2B   4    0.981110    0.155727    0.564171    11.00000    0.03703    0.05639 =
         0.16420    0.00756    0.00385   -0.01098
C4B   1    1.014997    0.047774    0.555562    11.00000    0.04733    0.07731 =
         0.09787    0.00897    0.00414    0.01461
AFIX  23
H4E  2    1.032731    0.041940    0.484541    11.00000   -1.20000
H4F  2    1.069450    0.058637    0.593612    11.00000   -1.20000
AFIX   0
C5B   1    0.983409   -0.010069    0.592144    11.00000    0.04961    0.06463 =
         0.17916    0.01471    0.01365    0.02341
AFIX  23
H5E  2    0.984259   -0.008306    0.666469    11.00000   -1.20000
H5F  2    1.026355   -0.042644    0.571579    11.00000   -1.20000
AFIX   0
C6B   1    0.892997   -0.030725    0.560473    11.00000    0.06517    0.03740 =
         0.04654   -0.00232    0.00448    0.01289
AFIX  23
H6E  2    0.896043   -0.051224    0.493926    11.00000   -1.20000
H6F  2    0.868801   -0.060965    0.609553    11.00000   -1.20000
AFIX   0
C7B   1    0.773587    0.118669    0.552379    11.00000    0.03594    0.03315 =
         0.02259   -0.00115    0.00115   -0.00363
C8B   1    0.749235    0.185108    0.549370    11.00000    0.04125    0.03591 =
         0.02813    0.00115   -0.00576    0.00391
C9B   1    0.661438    0.204671    0.533724    11.00000    0.04669    0.04985 =
         0.02830   -0.00384   -0.00282    0.00147
O3B   4    0.591460    0.164169    0.524850    11.00000    0.03573    0.05976 =
         0.06555   -0.00716   -0.00099    0.00787
H3B   2    0.620991    0.125333    0.530094    11.00000   -1.50000
C10B  1    0.640246    0.266971    0.529768    11.00000    0.06773    0.04989 =
         0.03973   -0.00251   -0.00080    0.02343
AFIX  43
H10B  2    0.580189    0.279262    0.519469    11.00000   -1.20000
AFIX   0
C11B  1    0.705121    0.311588    0.540570    11.00000    0.08674    0.04126 =
         0.03994   -0.00038   -0.00243    0.01839
AFIX  43
H11B  2    0.690246    0.354495    0.535587    11.00000   -1.20000
AFIX   0
C12B  1    0.792371    0.293801    0.558768    11.00000    0.08024    0.03584 =
         0.04229    0.00449   -0.00516   -0.00336
AFIX  43
H12B  2    0.836906    0.324593    0.568845    11.00000   -1.20000
AFIX   0
C13B  1    0.814712    0.231289    0.562281    11.00000    0.05560    0.03627 =
         0.04209    0.00047   -0.00888   -0.00295
AFIX  43
H13B  2    0.874820    0.219446    0.573514    11.00000   -1.20000
AFIX   0
N1C   3    0.290599    0.330460    0.785455    11.00000    0.03333    0.03770 =
         0.03480    0.00067   -0.00401    0.00112
O1C   4    0.256637    0.269380    0.785964    11.00000    0.04482    0.03726 =
         0.03493    0.00148   -0.00190    0.00768
C1C   1    0.168354    0.273003    0.774808    11.00000    0.03842    0.03856 =
         0.02118   -0.00252    0.00160    0.00135
C2C   1    0.141432    0.332828    0.766919    11.00000    0.03168    0.03418 =
         0.02734   -0.00267    0.00176    0.00164
C3C   1    0.046691    0.345240    0.746185    11.00000    0.03944    0.04996 =
         0.05237   -0.00520    0.00667    0.00462
O2C   4    0.015709    0.396715    0.729522    11.00000    0.04316    0.06017 =
         0.11315    0.00294   -0.00474    0.01422
C4C   1   -0.010895    0.288939    0.736743    11.00000    0.04128    0.05879 =
         0.08663    0.00880   -0.00739   -0.00710
AFIX  23
H4G  2   -0.010849    0.275156    0.665756    11.00000   -1.20000
H4H  2   -0.072729    0.300441    0.754542    11.00000   -1.20000
AFIX   0
C5C   1    0.019213    0.232850    0.805029    11.00000    0.05290    0.06180 =
         0.07757    0.00716    0.01705   -0.01912
AFIX  23
H5G  2    0.016327    0.245052    0.876690    11.00000   -1.20000
H5H  2   -0.020922    0.196842    0.794625    11.00000   -1.20000
AFIX   0
C6C   1    0.114713    0.214967    0.777115    11.00000    0.05603    0.04343 =
         0.03833   -0.00420    0.00163   -0.00904
AFIX  23
H6G  2    0.139294    0.185654    0.827399    11.00000   -1.20000
H6H  2    0.115851    0.194483    0.710480    11.00000   -1.20000
AFIX   0
C7C   1    0.222726    0.368783    0.775608    11.00000    0.03155    0.04277 =
         0.01673    0.00095   -0.00133   -0.00062
C8C   1    0.241484    0.435839    0.776157    11.00000    0.04661    0.04082 =
         0.02083   -0.00006    0.00139   -0.00154
C9C   1    0.328700    0.458570    0.791101    11.00000    0.05258    0.05170 =
         0.02672    0.00370    0.00290   -0.01607
O3C   4    0.401280    0.421399    0.801674    11.00000    0.04321    0.06872 =
         0.05876    0.00747   -0.00582   -0.01445
H3C   2    0.381959    0.381717    0.814099    11.00000   -1.50000
C10C  1    0.343943    0.521849    0.796493    11.00000    0.07178    0.05651 =
         0.04742    0.00415   -0.00169   -0.02848
AFIX  43
H10C  2    0.402480    0.536660    0.809061    11.00000   -1.20000
AFIX   0
C11C  1    0.275824    0.563744    0.783978    11.00000    0.11047    0.03853 =
         0.04569    0.00217    0.00521   -0.01700
AFIX  43
H11C  2    0.287811    0.607176    0.786376    11.00000   -1.20000
AFIX   0
C12C  1    0.190507    0.543212    0.768022    11.00000    0.08584    0.04195 =
         0.04073   -0.00518    0.00093    0.00275
AFIX  43
H12C  2    0.143320    0.572132    0.758950    11.00000   -1.20000
AFIX   0
C13C  1    0.174138    0.479737    0.765327    11.00000    0.06435    0.03854 =
         0.03381   -0.00357   -0.00106    0.00028
AFIX  43
H13C  2    0.114777    0.465697    0.755735    11.00000   -1.20000
 
HKLF 4
 
REM  4a in Pca2(1)
REM R1 =  0.0564 for   5081 Fo > 4sig(Fo)  and  0.1218 for all   8811 data
REM    625 parameters refined using      1 restraints
 
END  
     
WGHT      0.0580      2.9564 
REM Highest difference peak  0.403,  deepest hole -0.290,  1-sigma level  0.051
Q1    1   0.9853 -0.0079  0.5156  11.00000  0.05    0.40
Q2    1   0.0095  0.3553  0.1042  11.00000  0.05    0.32
Q3    1   0.0058  0.3664 -0.0053  11.00000  0.05    0.29
Q4    1   0.4734  0.7302  0.2272  11.00000  0.05    0.27
Q5    1   0.0113  0.3875  0.8271  11.00000  0.05    0.26
Q6    1   0.4861  0.9020  0.2351  11.00000  0.05    0.25
Q7    1   0.1011  0.5848  0.7623  11.00000  0.05    0.25
Q8    1   0.3981  1.0842  0.3083  11.00000  0.05    0.25
Q9    1   0.0329  0.5269  0.0979  11.00000  0.05    0.22
Q10   1   0.0825  0.1697  0.0466  11.00000  0.05    0.21

;
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_6b
_database_code_depnum_ccdc_archive 'CCDC 962973'
_audit_update_record             
;
2013-09-24 deposited with the CCDC.
2014-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N O3'
_chemical_formula_sum            'C15 H15 N O3'
_chemical_formula_weight         257.28

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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   12.930(2)
_cell_length_b                   9.3159(15)
_cell_length_c                   21.663(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2609.4(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6477
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      26.57

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.880
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   'SADABS v20012/1, Sheldrick, G.M., (2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX 2 CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            25390
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.880
_diffrn_reflns_theta_max         28.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6484
_reflns_number_gt                5459
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.945
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX 2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0467P)²+0.2254P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'all non-H found by direct methods'
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0018(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2399 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.2(4)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         6484
_refine_ls_number_parameters     464
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0882
_refine_ls_wR_factor_gt          0.0828
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.25042(14) 0.5775(2) 0.31200(9) 0.0240(4) Uani 1 1 d . . . . .
C1 C 0.31869(16) 0.6792(2) 0.30528(11) 0.0220(4) Uani 1 1 d . . . . .
O1 O 0.33046(11) 0.72508(17) 0.24541(8) 0.0223(3) Uani 1 1 d . . . . .
C2 C 0.26059(17) 0.6458(2) 0.21303(11) 0.0225(5) Uani 1 1 d . . . . .
C3 C 0.21266(17) 0.5562(2) 0.25242(11) 0.0227(4) Uani 1 1 d . . . . .
C4 C 0.12971(17) 0.4603(2) 0.23212(12) 0.0249(5) Uani 1 1 d . . . . .
C5 C 0.1108(2) 0.4653(3) 0.16294(12) 0.0294(5) Uani 1 1 d . . . . .
H5A H 0.156(2) 0.392(3) 0.1421(13) 0.030(7) Uiso 1 1 d . . . . .
H5B H 0.039(2) 0.433(3) 0.1538(15) 0.041(8) Uiso 1 1 d . . . . .
C6 C 0.13039(18) 0.6120(3) 0.13172(11) 0.0263(5) Uani 1 1 d . . . . .
C7 C 0.24231(18) 0.6633(3) 0.14594(11) 0.0253(5) Uani 1 1 d . . . . .
H7A H 0.295(2) 0.603(3) 0.1211(14) 0.034(7) Uiso 1 1 d . . . . .
H7B H 0.247(2) 0.767(3) 0.1348(13) 0.030(7) Uiso 1 1 d . . . . .
C8 C 0.1177(2) 0.5949(4) 0.06175(13) 0.0376(6) Uani 1 1 d . . . . .
H8A H 0.134(3) 0.684(4) 0.0392(16) 0.054(10) Uiso 1 1 d . . . . .
H8B H 0.163(2) 0.516(3) 0.0468(12) 0.031(7) Uiso 1 1 d . . . . .
H8C H 0.046(2) 0.573(3) 0.0522(13) 0.034(7) Uiso 1 1 d . . . . .
C9 C 0.0514(2) 0.7225(3) 0.15476(13) 0.0316(5) Uani 1 1 d . . . . .
H9A H 0.061(2) 0.745(3) 0.2002(14) 0.030(7) Uiso 1 1 d . . . . .
H9B H 0.059(2) 0.810(4) 0.1296(15) 0.039(8) Uiso 1 1 d . . . . .
H9C H -0.020(2) 0.685(3) 0.1475(15) 0.042(8) Uiso 1 1 d . . . . .
C10 C 0.37876(17) 0.7474(2) 0.35349(12) 0.0234(5) Uani 1 1 d . . . . .
C11 C 0.36281(18) 0.7082(3) 0.41531(12) 0.0271(5) Uani 1 1 d . . . . .
O3 O 0.29198(15) 0.6065(2) 0.43206(9) 0.0363(4) Uani 1 1 d . . . . .
H3 H 0.263(3) 0.575(5) 0.395(2) 0.081(14) Uiso 1 1 d . . . . .
O2 O 0.08210(13) 0.38227(19) 0.26697(9) 0.0339(4) Uani 1 1 d . . . . .
C12 C 0.4212(2) 0.7730(3) 0.46145(14) 0.0337(6) Uani 1 1 d . . . . .
H12 H 0.411(2) 0.746(3) 0.5028(18) 0.039(9) Uiso 1 1 d . . . . .
C13 C 0.4945(2) 0.8758(3) 0.44639(13) 0.0340(6) Uani 1 1 d . . . . .
H13 H 0.537(2) 0.916(3) 0.4802(14) 0.035(8) Uiso 1 1 d . . . . .
C14 C 0.50956(19) 0.9170(3) 0.38555(13) 0.0311(5) Uani 1 1 d . . . . .
H14 H 0.561(2) 0.987(3) 0.3772(12) 0.031(7) Uiso 1 1 d . . . . .
C15 C 0.45163(18) 0.8537(3) 0.33944(12) 0.0273(5) Uani 1 1 d . . . . .
H15 H 0.463(2) 0.882(3) 0.2950(14) 0.028(7) Uiso 1 1 d . . . . .
N2 N 0.48457(14) 0.4198(2) 0.23943(8) 0.0226(4) Uani 1 1 d . . . . .
C16 C 0.41519(16) 0.3203(2) 0.24491(11) 0.0214(4) Uani 1 1 d . . . . .
O4 O 0.39970(11) 0.27372(17) 0.30442(8) 0.0219(3) Uani 1 1 d . . . . .
C17 C 0.46955(16) 0.3509(2) 0.33827(11) 0.0219(5) Uani 1 1 d . . . . .
C18 C 0.52108(16) 0.4398(2) 0.29962(10) 0.0213(4) Uani 1 1 d . . . . .
C19 C 0.60382(18) 0.5331(2) 0.32139(11) 0.0240(5) Uani 1 1 d . . . . .
O5 O 0.65580(13) 0.60786(18) 0.28721(8) 0.0324(4) Uani 1 1 d . . . . .
C20 C 0.6177(2) 0.5307(3) 0.39102(12) 0.0272(5) Uani 1 1 d . . . . .
H20A H 0.569(2) 0.608(3) 0.4073(13) 0.025(7) Uiso 1 1 d . . . . .
H20B H 0.689(2) 0.561(3) 0.3990(14) 0.036(8) Uiso 1 1 d . . . . .
C21 C 0.59347(18) 0.3867(3) 0.42331(11) 0.0270(5) Uani 1 1 d . . . . .
C22 C 0.48378(19) 0.3330(3) 0.40542(11) 0.0264(5) Uani 1 1 d . . . . .
H22A H 0.4749(18) 0.232(3) 0.4170(12) 0.019(6) Uiso 1 1 d . . . . .
H22B H 0.428(2) 0.388(3) 0.4279(15) 0.038(7) Uiso 1 1 d . . . . .
C23 C 0.6746(2) 0.2752(3) 0.40589(14) 0.0336(6) Uani 1 1 d . . . . .
H23A H 0.673(2) 0.251(3) 0.3612(15) 0.030(7) Uiso 1 1 d . . . . .
H23B H 0.668(2) 0.181(3) 0.4289(14) 0.039(8) Uiso 1 1 d . . . . .
H23C H 0.744(3) 0.312(3) 0.4143(15) 0.049(9) Uiso 1 1 d . . . . .
C24 C 0.5954(2) 0.4107(4) 0.49334(13) 0.0397(6) Uani 1 1 d . . . . .
H24A H 0.582(3) 0.314(4) 0.5157(17) 0.054(10) Uiso 1 1 d . . . . .
H24B H 0.539(3) 0.483(4) 0.5043(16) 0.066(11) Uiso 1 1 d . . . . .
H24C H 0.667(3) 0.443(4) 0.5052(16) 0.055(9) Uiso 1 1 d . . . . .
C25 C 0.35796(17) 0.2520(2) 0.19534(12) 0.0218(5) Uani 1 1 d . . . . .
C26 C 0.37963(18) 0.2915(3) 0.13356(11) 0.0278(5) Uani 1 1 d . . . . .
O6 O 0.45127(15) 0.3924(2) 0.11938(9) 0.0378(5) Uani 1 1 d . . . . .
H6 H 0.477(2) 0.422(3) 0.1565(18) 0.046(9) Uiso 1 1 d . . . . .
C27 C 0.3267(2) 0.2237(3) 0.08570(13) 0.0333(6) Uani 1 1 d . . . . .
H27 H 0.339(2) 0.250(3) 0.0421(18) 0.044(9) Uiso 1 1 d . . . . .
C28 C 0.2541(2) 0.1193(3) 0.09846(13) 0.0355(6) Uani 1 1 d . . . . .
H28 H 0.217(2) 0.072(3) 0.0645(15) 0.043(8) Uiso 1 1 d . . . . .
C29 C 0.2324(2) 0.0801(3) 0.15889(13) 0.0329(6) Uani 1 1 d . . . . .
H29 H 0.184(2) 0.011(4) 0.1675(14) 0.043(9) Uiso 1 1 d . . . . .
C30 C 0.28404(18) 0.1456(3) 0.20701(12) 0.0272(5) Uani 1 1 d . . . . .
H30 H 0.271(2) 0.117(3) 0.2491(15) 0.032(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
N1 C1 1.303(3) . ?
N1 C3 1.394(3) . ?
C1 O1 1.374(3) . ?
C1 C10 1.448(3) . ?
O1 C2 1.362(3) . ?
C2 C3 1.345(3) . ?
C2 C7 1.482(3) . ?
C3 C4 1.464(3) . ?
C4 O2 1.215(3) . ?
C4 C5 1.519(4) . ?
C5 C6 1.546(4) . ?
C6 C8 1.533(4) . ?
C6 C9 1.534(3) . ?
C6 C7 1.555(3) . ?
C10 C15 1.401(3) . ?
C10 C11 1.403(4) . ?
C11 O3 1.367(3) . ?
C11 C12 1.391(4) . ?
C12 C13 1.386(4) . ?
C13 C14 1.386(4) . ?
C14 C15 1.381(4) . ?
N2 C16 1.296(3) . ?
N2 C18 1.399(3) . ?
C16 O4 1.375(3) . ?
C16 C25 1.451(3) . ?
O4 C17 1.368(3) . ?
C17 C18 1.353(3) . ?
C17 C22 1.476(3) . ?
C18 C19 1.457(3) . ?
C19 O5 1.219(3) . ?
C19 C20 1.519(3) . ?
C20 C21 1.545(3) . ?
C21 C23 1.524(4) . ?
C21 C24 1.534(3) . ?
C21 C22 1.553(3) . ?
C25 C30 1.400(3) . ?
C25 C26 1.416(4) . ?
C26 O6 1.355(3) . ?
C26 C27 1.393(4) . ?
C27 C28 1.381(4) . ?
C28 C29 1.388(4) . ?
C29 C30 1.381(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
C1 N1 C3 103.72(19) . . ?
N1 C1 O1 114.0(2) . . ?
N1 C1 C10 127.0(2) . . ?
O1 C1 C10 119.0(2) . . ?
C2 O1 C1 104.11(18) . . ?
C3 C2 O1 108.4(2) . . ?
C3 C2 C7 128.1(2) . . ?
O1 C2 C7 123.4(2) . . ?
C2 C3 N1 109.7(2) . . ?
C2 C3 C4 121.7(2) . . ?
N1 C3 C4 128.4(2) . . ?
O2 C4 C3 123.3(2) . . ?
O2 C4 C5 123.4(2) . . ?
C3 C4 C5 113.3(2) . . ?
C4 C5 C6 115.6(2) . . ?
C8 C6 C9 108.7(2) . . ?
C8 C6 C5 108.9(2) . . ?
C9 C6 C5 110.0(2) . . ?
C8 C6 C7 109.1(2) . . ?
C9 C6 C7 110.5(2) . . ?
C5 C6 C7 109.7(2) . . ?
C2 C7 C6 108.00(19) . . ?
C15 C10 C11 119.4(2) . . ?
C15 C10 C1 121.0(2) . . ?
C11 C10 C1 119.7(2) . . ?
O3 C11 C12 118.3(2) . . ?
O3 C11 C10 122.2(2) . . ?
C12 C11 C10 119.5(2) . . ?
C13 C12 C11 120.1(3) . . ?
C12 C13 C14 120.8(2) . . ?
C15 C14 C13 119.5(2) . . ?
C14 C15 C10 120.6(3) . . ?
C16 N2 C18 104.09(19) . . ?
N2 C16 O4 114.4(2) . . ?
N2 C16 C25 126.8(2) . . ?
O4 C16 C25 118.76(19) . . ?
C17 O4 C16 103.93(17) . . ?
C18 C17 O4 108.4(2) . . ?
C18 C17 C22 128.1(2) . . ?
O4 C17 C22 123.5(2) . . ?
C17 C18 N2 109.20(19) . . ?
C17 C18 C19 121.8(2) . . ?
N2 C18 C19 129.0(2) . . ?
O5 C19 C18 123.3(2) . . ?
O5 C19 C20 123.1(2) . . ?
C18 C19 C20 113.6(2) . . ?
C19 C20 C21 116.0(2) . . ?
C23 C21 C24 109.5(2) . . ?
C23 C21 C20 109.8(2) . . ?
C24 C21 C20 108.5(2) . . ?
C23 C21 C22 110.4(2) . . ?
C24 C21 C22 108.0(2) . . ?
C20 C21 C22 110.6(2) . . ?
C17 C22 C21 108.89(19) . . ?
C30 C25 C26 119.3(2) . . ?
C30 C25 C16 121.7(2) . . ?
C26 C25 C16 119.0(2) . . ?
O6 C26 C27 118.8(2) . . ?
O6 C26 C25 122.0(2) . . ?
C27 C26 C25 119.2(2) . . ?
C28 C27 C26 120.3(3) . . ?
C27 C28 C29 120.8(3) . . ?
C30 C29 C28 119.9(3) . . ?
C29 C30 C25 120.5(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
C3 N1 C1 O1 -1.2(2) . . . . ?
C3 N1 C1 C10 177.3(2) . . . . ?
N1 C1 O1 C2 1.6(2) . . . . ?
C10 C1 O1 C2 -176.98(18) . . . . ?
C1 O1 C2 C3 -1.3(2) . . . . ?
C1 O1 C2 C7 177.2(2) . . . . ?
O1 C2 C3 N1 0.7(2) . . . . ?
C7 C2 C3 N1 -177.8(2) . . . . ?
O1 C2 C3 C4 177.44(19) . . . . ?
C7 C2 C3 C4 -1.0(4) . . . . ?
C1 N1 C3 C2 0.3(2) . . . . ?
C1 N1 C3 C4 -176.2(2) . . . . ?
C2 C3 C4 O2 -177.0(2) . . . . ?
N1 C3 C4 O2 -0.9(4) . . . . ?
C2 C3 C4 C5 4.4(3) . . . . ?
N1 C3 C4 C5 -179.5(2) . . . . ?
O2 C4 C5 C6 149.0(2) . . . . ?
C3 C4 C5 C6 -32.4(3) . . . . ?
C4 C5 C6 C8 174.8(2) . . . . ?
C4 C5 C6 C9 -66.3(3) . . . . ?
C4 C5 C6 C7 55.4(3) . . . . ?
C3 C2 C7 C6 23.8(3) . . . . ?
O1 C2 C7 C6 -154.5(2) . . . . ?
C8 C6 C7 C2 -166.7(2) . . . . ?
C9 C6 C7 C2 73.9(3) . . . . ?
C5 C6 C7 C2 -47.5(3) . . . . ?
N1 C1 C10 C15 178.5(2) . . . . ?
O1 C1 C10 C15 -3.1(3) . . . . ?
N1 C1 C10 C11 -2.5(3) . . . . ?
O1 C1 C10 C11 175.9(2) . . . . ?
C15 C10 C11 O3 179.2(2) . . . . ?
C1 C10 C11 O3 0.2(3) . . . . ?
C15 C10 C11 C12 -1.5(3) . . . . ?
C1 C10 C11 C12 179.5(2) . . . . ?
O3 C11 C12 C13 179.4(2) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
C11 C12 C13 C14 1.0(4) . . . . ?
C12 C13 C14 C15 -0.7(4) . . . . ?
C13 C14 C15 C10 -0.7(4) . . . . ?
C11 C10 C15 C14 1.8(3) . . . . ?
C1 C10 C15 C14 -179.2(2) . . . . ?
C18 N2 C16 O4 1.6(2) . . . . ?
C18 N2 C16 C25 -175.5(2) . . . . ?
N2 C16 O4 C17 -1.9(2) . . . . ?
C25 C16 O4 C17 175.56(18) . . . . ?
C16 O4 C17 C18 1.2(2) . . . . ?
C16 O4 C17 C22 -177.8(2) . . . . ?
O4 C17 C18 N2 -0.3(2) . . . . ?
C22 C17 C18 N2 178.6(2) . . . . ?
O4 C17 C18 C19 -177.75(19) . . . . ?
C22 C17 C18 C19 1.2(4) . . . . ?
C16 N2 C18 C17 -0.8(2) . . . . ?
C16 N2 C18 C19 176.4(2) . . . . ?
C17 C18 C19 O5 175.4(2) . . . . ?
N2 C18 C19 O5 -1.5(4) . . . . ?
C17 C18 C19 C20 -5.8(3) . . . . ?
N2 C18 C19 C20 177.3(2) . . . . ?
O5 C19 C20 C21 -148.8(2) . . . . ?
C18 C19 C20 C21 32.4(3) . . . . ?
C19 C20 C21 C23 69.0(3) . . . . ?
C19 C20 C21 C24 -171.4(2) . . . . ?
C19 C20 C21 C22 -53.1(3) . . . . ?
C18 C17 C22 C21 -21.6(3) . . . . ?
O4 C17 C22 C21 157.2(2) . . . . ?
C23 C21 C22 C17 -77.4(3) . . . . ?
C24 C21 C22 C17 163.0(2) . . . . ?
C20 C21 C22 C17 44.4(3) . . . . ?
N2 C16 C25 C30 -179.7(2) . . . . ?
O4 C16 C25 C30 3.3(3) . . . . ?
N2 C16 C25 C26 2.1(3) . . . . ?
O4 C16 C25 C26 -175.0(2) . . . . ?
C30 C25 C26 O6 -179.2(2) . . . . ?
C16 C25 C26 O6 -0.9(3) . . . . ?
C30 C25 C26 C27 0.1(3) . . . . ?
C16 C25 C26 C27 178.4(2) . . . . ?
O6 C26 C27 C28 179.3(2) . . . . ?
C25 C26 C27 C28 0.0(4) . . . . ?
C26 C27 C28 C29 0.0(4) . . . . ?
C27 C28 C29 C30 -0.2(4) . . . . ?
C28 C29 C30 C25 0.3(4) . . . . ?
C26 C25 C30 C29 -0.3(3) . . . . ?
C16 C25 C30 C29 -178.5(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
O3 H3 N1 0.93(5) 1.81(5) 2.669(3) 153(4) .
O6 H6 N2 0.91(4) 1.80(4) 2.648(3) 154(3) .

_refine_diff_density_max         0.247
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.034

_shelxl_version_number           2012-9

_iucr_refine_instruction_details 
; 
TITL 6b in Pna2(1) 
CELL 0.71073  12.930   9.3159  21.663  90.000  90.000  90.000 
ZERR    8.00   0.002   0.0015   0.004   0.000   0.000   0.000 
LATT -1 
SYMM -X, -Y, 0.5+Z 
SYMM 0.5+X, 0.5-Y, Z 
SYMM 0.5-X, 0.5+Y, 0.5+Z 
SFAC C H N O 
UNIT 120 120 8 24 
TEMP -123 
SIZE 0.06 0.40 0.88 
  
ACTA 
CONF 
WPDB -1 
  
L.S. 6 
BOND 
FMAP 2 
PLAN 10 
  
HTAB O3 N1 
HTAB O6 N2 
  
WGHT    0.046700    0.225400 
EXTI    0.001776 
FVAR       0.16102 
N1    3    0.250417    0.577524    0.312004    11.00000    0.02047    0.02246 = 
         0.02894    0.00042   -0.00138    0.00071 
C1    1    0.318686    0.679173    0.305277    11.00000    0.01890    0.02234 = 
         0.02469    0.00002    0.00177    0.00298 
O1    4    0.330464    0.725077    0.245407    11.00000    0.02029    0.02285 = 
         0.02389   -0.00145    0.00026   -0.00123 
C2    1    0.260587    0.645752    0.213031    11.00000    0.01768    0.01984 = 
         0.02984   -0.00359   -0.00162    0.00069 
C3    1    0.212657    0.556212    0.252417    11.00000    0.02053    0.01870 = 
         0.02901   -0.00089   -0.00052    0.00214 
C4    1    0.129707    0.460284    0.232123    11.00000    0.02033    0.01865 = 
         0.03575   -0.00296    0.00172    0.00134 
C5    1    0.110826    0.465328    0.162941    11.00000    0.02670    0.02603 = 
         0.03535   -0.00798   -0.00058   -0.00187 
H5A   2    0.156472    0.392027    0.142055    11.00000    0.02983 
H5B   2    0.039034    0.433140    0.153771    11.00000    0.04118 
C6    1    0.130391    0.612031    0.131715    11.00000    0.02430    0.02906 = 
         0.02540   -0.00507   -0.00266    0.00037 
C7    1    0.242307    0.663311    0.145936    11.00000    0.02485    0.02669 = 
         0.02427   -0.00005    0.00169   -0.00037 
H7A   2    0.295151    0.603167    0.121071    11.00000    0.03406 
H7B   2    0.247387    0.766840    0.134828    11.00000    0.03002 
C8    1    0.117704    0.594932    0.061754    11.00000    0.03783    0.04646 = 
         0.02852   -0.00817   -0.00547   -0.00247 
H8A   2    0.133978    0.684412    0.039216    11.00000    0.05401 
H8B   2    0.162694    0.516038    0.046777    11.00000    0.03093 
H8C   2    0.045816    0.573227    0.052205    11.00000    0.03359 
C9    1    0.051357    0.722479    0.154763    11.00000    0.02821    0.03115 = 
         0.03545   -0.00507   -0.00500    0.00575 
H9A   2    0.060914    0.744570    0.200221    11.00000    0.03049 
H9B   2    0.058672    0.809885    0.129617    11.00000    0.03914 
H9C   2   -0.019884    0.685132    0.147458    11.00000    0.04154 
C10   1    0.378765    0.747383    0.353491    11.00000    0.02036    0.02252 = 
         0.02725   -0.00321    0.00082    0.00225 
C11   1    0.362805    0.708169    0.415305    11.00000    0.02430    0.02862 = 
         0.02853   -0.00194    0.00353    0.00271 
O3    4    0.291980    0.606464    0.432058    11.00000    0.03663    0.04387 = 
         0.02827    0.00333    0.00250   -0.01050 
H3    2    0.263164    0.574817    0.395028    11.00000    0.08083 
O2    4    0.082103    0.382271    0.266967    11.00000    0.03236    0.02662 = 
         0.04276    0.00077    0.00336   -0.00923 
C12   1    0.421193    0.773021    0.461455    11.00000    0.03675    0.03995 = 
         0.02439   -0.00644    0.00035    0.00264 
H12   2    0.411237    0.746385    0.502809    11.00000    0.03865 
C13   1    0.494491    0.875760    0.446386    11.00000    0.03091    0.03566 = 
         0.03554   -0.01601   -0.00091    0.00239 
H13   2    0.536849    0.915925    0.480195    11.00000    0.03525 
C14   1    0.509561    0.917007    0.385553    11.00000    0.02467    0.02876 = 
         0.03978   -0.00847    0.00140   -0.00113 
H14   2    0.561020    0.987065    0.377208    11.00000    0.03134 
C15   1    0.451633    0.853734    0.339445    11.00000    0.02491    0.02697 = 
         0.02997   -0.00385    0.00060    0.00061 
H15   2    0.463245    0.882223    0.294967    11.00000    0.02767 
N2    3    0.484571    0.419820    0.239427    11.00000    0.02269    0.02095 = 
         0.02426    0.00170    0.00002    0.00008 
C16   1    0.415188    0.320303    0.244912    11.00000    0.02096    0.02030 = 
         0.02291    0.00112    0.00022    0.00319 
O4    4    0.399697    0.273723    0.304417    11.00000    0.02017    0.02335 = 
         0.02210   -0.00094   -0.00028   -0.00196 
C17   1    0.469555    0.350864    0.338270    11.00000    0.01908    0.02132 = 
         0.02517   -0.00287   -0.00051    0.00075 
C18   1    0.521079    0.439829    0.299618    11.00000    0.02063    0.02047 = 
         0.02275   -0.00027    0.00007    0.00155 
C19   1    0.603823    0.533075    0.321389    11.00000    0.02346    0.01712 = 
         0.03131   -0.00201    0.00069    0.00086 
O5    4    0.655802    0.607858    0.287211    11.00000    0.03099    0.02876 = 
         0.03758    0.00054    0.00201   -0.00884 
C20   1    0.617742    0.530657    0.391023    11.00000    0.02489    0.02585 = 
         0.03095   -0.00630   -0.00290   -0.00250 
H20A  2    0.569117    0.608468    0.407268    11.00000    0.02486 
H20A  2    0.689298    0.561096    0.399025    11.00000    0.03637 
C21   1    0.593470    0.386651    0.423313    11.00000    0.02960    0.02676 = 
         0.02479   -0.00468   -0.00279   -0.00049 
C22   1    0.483785    0.333012    0.405417    11.00000    0.02699    0.02894 = 
         0.02314   -0.00133    0.00107   -0.00269 
H22A  2    0.474949    0.232306    0.416978    11.00000    0.01876 
H22B  2    0.428311    0.388259    0.427861    11.00000    0.03766 
C23   1    0.674637    0.275201    0.405889    11.00000    0.02888    0.03337 = 
         0.03865   -0.00095   -0.00778    0.00234 
H23A  2    0.672553    0.250720    0.361185    11.00000    0.02974 
H23B  2    0.668381    0.180942    0.428895    11.00000    0.03906 
H23C  2    0.743678    0.312097    0.414265    11.00000    0.04879 
C24   1    0.595416    0.410686    0.493339    11.00000    0.04566    0.04874 = 
         0.02469   -0.00574   -0.00588   -0.00689 
H24A  2    0.582480    0.314244    0.515669    11.00000    0.05448 
H24B  2    0.539197    0.482681    0.504300    11.00000    0.06556 
H24C  2    0.667036    0.443053    0.505183    11.00000    0.05460 
C25   1    0.357961    0.251994    0.195344    11.00000    0.02001    0.02213 = 
         0.02340    0.00014   -0.00230    0.00422 
C26   1    0.379630    0.291457    0.133556    11.00000    0.02828    0.02784 = 
         0.02733    0.00234   -0.00152    0.00390 
O6    4    0.451275    0.392430    0.119381    11.00000    0.04105    0.04787 = 
         0.02454    0.00822   -0.00146   -0.01147 
H6    2    0.476923    0.422259    0.156543    11.00000    0.04622 
C27   1    0.326746    0.223693    0.085701    11.00000    0.03864    0.03653 = 
         0.02464   -0.00322   -0.00378    0.00853 
H27   2    0.338539    0.250217    0.042098    11.00000    0.04436 
C28   1    0.254053    0.119286    0.098460    11.00000    0.03826    0.03284 = 
         0.03532   -0.00843   -0.01269    0.00476 
H28   2    0.216670    0.072465    0.064491    11.00000    0.04286 
C29   1    0.232355    0.080054    0.158893    11.00000    0.03071    0.02713 = 
         0.04091   -0.00473   -0.00730   -0.00278 
H29   2    0.183664    0.010805    0.167523    11.00000    0.04325 
C30   1    0.284039    0.145588    0.207014    11.00000    0.02606    0.02616 = 
         0.02939   -0.00027   -0.00093   -0.00072 
H30   2    0.270640    0.116801    0.249086    11.00000    0.03199 
HKLF 4 
  
REM  6b in Pna2(1) 
REM R1 =  0.0354 for    5459 Fo > 4sig(Fo)  and  0.0457 for all    6484 data 
REM    464 parameters refined using      1 restraints 
  
END 
  
WGHT      0.0442      0.2680 
  
REM Highest difference peak  0.247,  deepest hole -0.162,  1-sigma level  0.034 
Q1    1   0.6007  0.3947  0.4571  11.00000  0.05    0.25 
Q2    1   0.3759  0.2516  0.1638  11.00000  0.05    0.25 
Q3    1   0.1346  0.6046  0.0975  11.00000  0.05    0.24 
Q4    1   0.3768  0.7246  0.3823  11.00000  0.05    0.23 
Q5    1   0.6200  0.5168  0.3550  11.00000  0.05    0.23 
Q6    1   0.1132  0.4741  0.1982  11.00000  0.05    0.22 
Q7    1   0.4411  0.7690  0.3486  11.00000  0.05    0.21 
Q8    1   0.2105  0.6257  0.2325  11.00000  0.05    0.21 
Q9    1   0.1873  0.6280  0.1393  11.00000  0.05    0.21 
Q10   1   0.5210  0.3680  0.3162  11.00000  0.05    0.20 
;
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_7a
_database_code_depnum_ccdc_archive 'CCDC 962974'
_audit_update_record             
;
2013-09-24 deposited with the CCDC.
2014-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H13 N O4'
_chemical_formula_sum            'C13 H13 N O4'
_chemical_formula_weight         247.24

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   5.5001(6)
_cell_length_b                   15.2463(18)
_cell_length_c                   13.6680(16)
_cell_angle_alpha                90
_cell_angle_beta                 97.7388(18)
_cell_angle_gamma                90
_cell_volume                     1135.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6269
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      30.56

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.020
_exptl_crystal_size_mid          0.790
_exptl_crystal_size_min          0.380
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   0.898
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_process_details   'SADABS v2009/1, Sheldrick, G.M., (2009)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX 2 CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12997
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.011
_diffrn_reflns_theta_max         30.578
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3446
_reflns_number_gt                2970
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX 2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0800P)²+0.2403P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3446
_refine_ls_number_parameters     201
_refine_ls_number_restraints     35
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1314
_refine_ls_wR_factor_gt          0.1257
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.13899(18) 0.50029(6) 0.73465(7) 0.0213(2) Uani 1 1 d . . . . .
C2 C 0.02346(19) 0.50237(6) 0.81767(7) 0.0225(2) Uani 1 1 d . . . A .
O1 O -0.16208(15) 0.45174(5) 0.83427(6) 0.02943(19) Uani 1 1 d . . . . .
H1A H -0.198(4) 0.4131(14) 0.7766(16) 0.061(6) Uiso 1 1 d . . . . .
C3 C 0.1069(2) 0.56371(7) 0.90150(8) 0.0280(2) Uani 1 1 d . U . . .
H3A H 0.2256 0.5326 0.9504 0.034 Uiso 0.855(4) 1 calc R U P A 1
H3B H -0.0362 0.5799 0.9345 0.034 Uiso 0.855(4) 1 calc R U P A 1
H3C H 0.0893 0.5343 0.9647 0.034 Uiso 0.145(4) 1 calc R U P A 2
H3D H 0.0002 0.6163 0.8959 0.034 Uiso 0.145(4) 1 calc R U P A 2
C4 C 0.2250(2) 0.64604(8) 0.86986(9) 0.0264(3) Uani 0.855(4) 1 d . U P A 1
H4A H 0.2959 0.6797 0.9288 0.032 Uiso 0.855(4) 1 calc R U P A 1
H4B H 0.1001 0.6831 0.8306 0.032 Uiso 0.855(4) 1 calc R U P A 1
C5 C 0.4284(2) 0.62229(8) 0.80740(8) 0.0286(2) Uani 1 1 d . U . . .
H5A H 0.4873 0.6766 0.7786 0.034 Uiso 0.855(4) 1 calc R U P A 1
H5B H 0.5682 0.5962 0.8509 0.034 Uiso 0.855(4) 1 calc R U P A 1
H5C H 0.6080 0.6305 0.8114 0.034 Uiso 0.145(4) 1 calc R U P A 2
H5D H 0.3490 0.6798 0.7920 0.034 Uiso 0.145(4) 1 calc R U P A 2
C6 C 0.34399(19) 0.55883(7) 0.72539(8) 0.0233(2) Uani 1 1 d . . . A .
O2 O 0.44831(16) 0.55463(6) 0.65078(6) 0.03044(19) Uani 1 1 d . . . . .
C4X C 0.3702(14) 0.5919(6) 0.9025(6) 0.0293(19) Uani 0.145(4) 1 d . U P A 2
H4C H 0.4064 0.6397 0.9514 0.035 Uiso 0.145(4) 1 calc R U P A 2
H4D H 0.4787 0.5419 0.9245 0.035 Uiso 0.145(4) 1 calc R U P A 2
N1 N 0.08777(17) 0.44484(6) 0.65030(6) 0.02339(19) Uani 1 1 d . . . . .
H1 H 0.186(3) 0.4568(11) 0.6036(13) 0.042(4) Uiso 1 1 d . . . . .
C7 C -0.07395(19) 0.37978(7) 0.62977(7) 0.0233(2) Uani 1 1 d . . . . .
O3 O -0.21874(18) 0.35540(7) 0.68811(7) 0.0408(2) Uani 1 1 d . . . . .
C8 C -0.07667(18) 0.33236(6) 0.53416(7) 0.0215(2) Uani 1 1 d . . . . .
C9 C 0.09244(18) 0.34448(7) 0.46663(7) 0.0227(2) Uani 1 1 d . . . . .
O4 O 0.26533(15) 0.40812(6) 0.48428(6) 0.02946(19) Uani 1 1 d . . . . .
H4 H 0.356(3) 0.4140(12) 0.4339(14) 0.050(5) Uiso 1 1 d . . . . .
C10 C 0.0831(2) 0.29043(7) 0.38345(8) 0.0265(2) Uani 1 1 d . . . . .
H10 H 0.203(3) 0.2996(11) 0.3378(11) 0.033(4) Uiso 1 1 d . . . . .
C11 C -0.0971(2) 0.22665(7) 0.36500(8) 0.0289(2) Uani 1 1 d . . . . .
H11 H -0.101(3) 0.1888(11) 0.3065(12) 0.039(4) Uiso 1 1 d . . . . .
C12 C -0.2721(2) 0.21606(7) 0.42901(8) 0.0297(2) Uani 1 1 d . . . . .
H12 H -0.411(3) 0.1685(9) 0.4077(11) 0.026(3) Uiso 1 1 d . . . . .
C13 C -0.25934(19) 0.26839(7) 0.51249(8) 0.0257(2) Uani 1 1 d . . . . .
H13 H -0.374(3) 0.2599(10) 0.5589(11) 0.030(3) 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
C1 C2 1.3735(14) . ?
C1 N1 1.4268(12) . ?
C1 C6 1.4568(14) . ?
C2 O1 1.3233(13) . ?
C2 C3 1.5022(14) . ?
O1 H1A 0.98(2) . ?
C3 C4 1.5033(17) . ?
C3 C4X 1.509(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 H3C 0.9900 . ?
C3 H3D 0.9900 . ?
C4 C5 1.5387(16) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C4X 1.455(8) . ?
C5 C6 1.5059(15) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 H5C 0.9900 . ?
C5 H5D 0.9900 . ?
C6 O2 1.2373(13) . ?
C4X H4C 0.9900 . ?
C4X H4D 0.9900 . ?
N1 C7 1.3366(13) . ?
N1 H1 0.908(18) . ?
C7 O3 1.2567(13) . ?
C7 C8 1.4917(14) . ?
C8 C13 1.4030(14) . ?
C8 C9 1.4079(14) . ?
C9 O4 1.3573(12) . ?
C9 C10 1.3995(14) . ?
O4 H4 0.908(19) . ?
C10 C11 1.3869(16) . ?
C10 H10 0.979(16) . ?
C11 C12 1.3945(16) . ?
C11 H11 0.984(17) . ?
C12 C13 1.3863(15) . ?
C12 H12 1.066(14) . ?
C13 H13 0.962(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 128.19(9) . . ?
C2 C1 C6 120.47(9) . . ?
N1 C1 C6 111.33(8) . . ?
O1 C2 C1 125.55(9) . . ?
O1 C2 C3 113.33(9) . . ?
C1 C2 C3 121.11(9) . . ?
C2 O1 H1A 106.8(12) . . ?
C2 C3 C4 113.57(9) . . ?
C2 C3 C4X 112.3(3) . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C2 C3 H3C 109.2 . . ?
C4X C3 H3C 109.2 . . ?
C2 C3 H3D 109.2 . . ?
C4X C3 H3D 109.2 . . ?
H3C C3 H3D 107.9 . . ?
C3 C4 C5 109.72(10) . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C4X C5 C6 112.2(3) . . ?
C6 C5 C4 112.96(9) . . ?
C6 C5 H5A 109.0 . . ?
C4 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C4X C5 H5C 109.2 . . ?
C6 C5 H5C 109.2 . . ?
C4X C5 H5D 109.2 . . ?
C6 C5 H5D 109.2 . . ?
H5C C5 H5D 107.9 . . ?
O2 C6 C1 119.35(9) . . ?
O2 C6 C5 121.07(9) . . ?
C1 C6 C5 119.57(9) . . ?
C5 C4X C3 114.1(5) . . ?
C5 C4X H4C 108.7 . . ?
C3 C4X H4C 108.7 . . ?
C5 C4X H4D 108.7 . . ?
C3 C4X H4D 108.7 . . ?
H4C C4X H4D 107.6 . . ?
C7 N1 C1 131.51(9) . . ?
C7 N1 H1 116.2(11) . . ?
C1 N1 H1 112.2(11) . . ?
O3 C7 N1 123.16(10) . . ?
O3 C7 C8 118.69(9) . . ?
N1 C7 C8 118.13(9) . . ?
C13 C8 C9 118.06(9) . . ?
C13 C8 C7 116.38(9) . . ?
C9 C8 C7 125.53(9) . . ?
O4 C9 C10 120.91(9) . . ?
O4 C9 C8 119.09(9) . . ?
C10 C9 C8 120.00(9) . . ?
C9 O4 H4 112.3(12) . . ?
C11 C10 C9 120.52(10) . . ?
C11 C10 H10 120.8(9) . . ?
C9 C10 H10 118.6(9) . . ?
C10 C11 C12 120.24(10) . . ?
C10 C11 H11 119.7(10) . . ?
C12 C11 H11 120.0(10) . . ?
C13 C12 C11 119.15(10) . . ?
C13 C12 H12 124.9(8) . . ?
C11 C12 H12 115.9(8) . . ?
C12 C13 C8 121.95(10) . . ?
C12 C13 H13 120.1(9) . . ?
C8 C13 H13 117.9(9) . . ?

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
N1 C1 C2 O1 -0.19(17) . . . . ?
C6 C1 C2 O1 -179.24(9) . . . . ?
N1 C1 C2 C3 178.13(10) . . . . ?
C6 C1 C2 C3 -0.93(15) . . . . ?
O1 C2 C3 C4 -153.17(10) . . . . ?
C1 C2 C3 C4 28.33(14) . . . . ?
O1 C2 C3 C4X 156.0(4) . . . . ?
C1 C2 C3 C4X -22.5(4) . . . . ?
C2 C3 C4 C5 -51.74(13) . . . . ?
C4X C3 C4 C5 47.2(4) . . . . ?
C3 C4 C5 C4X -49.4(4) . . . . ?
C3 C4 C5 C6 50.13(13) . . . . ?
C2 C1 C6 O2 178.62(10) . . . . ?
N1 C1 C6 O2 -0.58(13) . . . . ?
C2 C1 C6 C5 -0.32(15) . . . . ?
N1 C1 C6 C5 -179.52(9) . . . . ?
C4X C5 C6 O2 -153.0(4) . . . . ?
C4 C5 C6 O2 155.99(11) . . . . ?
C4X C5 C6 C1 25.9(4) . . . . ?
C4 C5 C6 C1 -25.09(14) . . . . ?
C6 C5 C4X C3 -50.0(6) . . . . ?
C4 C5 C4X C3 51.3(4) . . . . ?
C2 C3 C4X C5 48.8(6) . . . . ?
C4 C3 C4X C5 -53.2(4) . . . . ?
C2 C1 N1 C7 -2.57(18) . . . . ?
C6 C1 N1 C7 176.55(10) . . . . ?
C1 N1 C7 O3 -0.25(18) . . . . ?
C1 N1 C7 C8 -178.40(9) . . . . ?
O3 C7 C8 C13 5.76(15) . . . . ?
N1 C7 C8 C13 -176.02(9) . . . . ?
O3 C7 C8 C9 -171.92(10) . . . . ?
N1 C7 C8 C9 6.31(15) . . . . ?
C13 C8 C9 O4 177.67(9) . . . . ?
C7 C8 C9 O4 -4.69(15) . . . . ?
C13 C8 C9 C10 -3.26(15) . . . . ?
C7 C8 C9 C10 174.38(10) . . . . ?
O4 C9 C10 C11 -178.79(10) . . . . ?
C8 C9 C10 C11 2.16(16) . . . . ?
C9 C10 C11 C12 0.40(17) . . . . ?
C10 C11 C12 C13 -1.76(17) . . . . ?
C11 C12 C13 C8 0.58(17) . . . . ?
C9 C8 C13 C12 1.92(16) . . . . ?
C7 C8 C13 C12 -175.94(10) . . . . ?

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 H1A N1 0.98(2) 2.53(2) 3.0254(12) 110.9(14) .
O1 H1A O3 0.98(2) 1.49(2) 2.4653(12) 172.7(19) .
N1 H1 O2 0.908(18) 2.116(17) 2.5944(12) 111.8(13) .
N1 H1 O4 0.908(18) 1.895(18) 2.6481(12) 139.0(15) .
O4 H4 O2 0.908(19) 1.75(2) 2.6446(11) 168.2(18) 3_666

_refine_diff_density_max         0.419
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.054

_shelxl_version_number           2012-6

_iucr_refine_instruction_details 
; 
TITL 7a in P2(1)/n 
CELL 0.71073   5.5001  15.2463  13.6680  90.000  97.7388  90.000 
ZERR    4.00   0.0006   0.0018   0.0016   0.000   0.0018   0.000 
LATT  1 
SYMM 0.5-X, 0.5+Y, 0.5-Z 
SFAC C H N O 
UNIT 52 52 4 16 
TEMP -123 
SIZE 0.38 0.79 1.02 
  
ACTA 
CONF 
WPDB -1 
  
L.S. 6 
BOND $H 
FMAP 2 
PLAN 10 
  
EQIV $1 -x+1, -y+1, -z+1 
HTAB O1 N1 
HTAB O1 O3 
HTAB N1 O2 
HTAB N1 O4 
HTAB O4 O2_$1 
  
SIMU C4 C4X C3 C5 
DELU C4 C4X C3 C5 
  
REM   EXTI    0.000000 
WGHT    0.080000    0.240300 
FVAR       0.20318   0.85506 
C1    1    0.138989    0.500288    0.734648    11.00000    0.02286    0.02140 = 
         0.02045    0.00032    0.00573   -0.00056 
C2    1    0.023463    0.502373    0.817667    11.00000    0.02356    0.02260 = 
         0.02226    0.00174    0.00643    0.00173 
O1    4   -0.162081    0.451741    0.834266    11.00000    0.03182    0.03073 = 
         0.02848   -0.00313    0.01405   -0.00684 
H1A   2   -0.198036    0.413148    0.776624    11.00000    0.06125 
C3    1    0.106942    0.563712    0.901495    11.00000    0.02979    0.03193 = 
         0.02312   -0.00321    0.00718   -0.00182 
PART 1 
AFIX  23 
H3A   2    0.225577    0.532623    0.950422    21.00000   -1.20000 
H3B   2   -0.036179    0.579947    0.934502    21.00000   -1.20000 
AFIX  23 
PART 2 
H3C   2    0.089331    0.534297    0.964732   -21.00000   -1.20000 
H3D   2    0.000231    0.616259    0.895936   -21.00000   -1.20000 
AFIX   0 
PART   1 
C4    1    0.225013    0.646039    0.869855    21.00000    0.02853    0.02733 = 
         0.02431   -0.00431    0.00692   -0.00189 
AFIX  23 
H4A   2    0.295885    0.679749    0.928776    21.00000   -1.20000 
H4B   2    0.100077    0.683134    0.830643    21.00000   -1.20000 
AFIX   0 
PART   0 
C5    1    0.428353    0.622286    0.807401    11.00000    0.02585    0.03122 = 
         0.02959   -0.00555    0.00673   -0.00560 
PART 1 
AFIX  23 
H5A   2    0.487282    0.676582    0.778562    21.00000   -1.20000 
H5B   2    0.568211    0.596202    0.850893    21.00000   -1.20000 
AFIX  23 
PART 2 
H5C   2    0.607962    0.630545    0.811438   -21.00000   -1.20000 
H5D   2    0.349019    0.679844    0.791987   -21.00000   -1.20000 
AFIX   0 
PART 0 
C6    1    0.343993    0.558825    0.725391    11.00000    0.02287    0.02359 = 
         0.02405    0.00110    0.00539   -0.00085 
O2    4    0.448312    0.554633    0.650779    11.00000    0.03153    0.03346 = 
         0.02904   -0.00189    0.01399   -0.00722 
PART   2 
C4X   1    0.370218    0.591946    0.902470   -21.00000    0.02620    0.03555 = 
         0.02617   -0.00291    0.00389   -0.00068 
AFIX  23 
H4C   2    0.406384    0.639676    0.951373   -21.00000   -1.20000 
H4D   2    0.478663    0.541910    0.924514   -21.00000   -1.20000 
AFIX   0 
PART   0 
N1    3    0.087772    0.444839    0.650298    11.00000    0.02623    0.02398 = 
         0.02144   -0.00112    0.00860   -0.00411 
H1    2    0.185798    0.456762    0.603562    11.00000    0.04192 
C7    1   -0.073945    0.379778    0.629771    11.00000    0.02445    0.02303 = 
         0.02337    0.00023    0.00688   -0.00107 
O3    4   -0.218742    0.355398    0.688114    11.00000    0.04762    0.04512 = 
         0.03493   -0.01261    0.02431   -0.02287 
C8    1   -0.076669    0.332363    0.534159    11.00000    0.02183    0.02126 = 
         0.02199    0.00084    0.00543    0.00018 
C9    1    0.092439    0.344478    0.466633    11.00000    0.02161    0.02427 = 
         0.02247    0.00244    0.00435   -0.00019 
O4    4    0.265331    0.408119    0.484284    11.00000    0.02897    0.03455 = 
         0.02725   -0.00492    0.01243   -0.00980 
H4    2    0.356029    0.414041    0.433866    11.00000    0.04979 
C10   1    0.083060    0.290433    0.383448    11.00000    0.02757    0.02994 = 
         0.02262   -0.00037    0.00614    0.00113 
H10   2    0.203466    0.299614    0.337813    11.00000    0.03295 
C11   1   -0.097063    0.226651    0.365000    11.00000    0.03383    0.02799 = 
         0.02464   -0.00304    0.00326    0.00005 
H11   2   -0.100974    0.188808    0.306525    11.00000    0.03857 
C12   1   -0.272067    0.216060    0.429010    11.00000    0.03185    0.02761 = 
         0.02982   -0.00174    0.00463   -0.00527 
H12   2   -0.411142    0.168482    0.407661    11.00000    0.02602 
C13   1   -0.259342    0.268386    0.512490    11.00000    0.02576    0.02480 = 
         0.02740    0.00073    0.00622   -0.00303 
H13   2   -0.373956    0.259939    0.558945    11.00000    0.02985 
  
HKLF 4 
  
REM  7a in P2(1)/n 
REM R1 =  0.0451 for    2970 Fo > 4sig(Fo)  and  0.0512 for all    3446 data 
REM    201 parameters refined using     35 restraints 
  
END 
  
WGHT      0.0800      0.2404 
  
REM Highest difference peak  0.419,  deepest hole -0.217,  1-sigma level  0.054 
Q1    1   0.0077  0.3403  0.4985  11.00000  0.05    0.42 
Q2    1  -0.0758  0.3559  0.5791  11.00000  0.05    0.41 
Q3    1   0.0628  0.5355  0.8579  11.00000  0.05    0.39 
Q4    1   0.2583  0.5230  0.7346  11.00000  0.05    0.38 
Q5    1   0.0841  0.5009  0.7760  11.00000  0.05    0.38 
Q6    1   0.0730  0.3231  0.4222  11.00000  0.05    0.36 
Q7    1   0.2075  0.5351  0.7245  11.00000  0.05    0.35 
Q8    1   0.3715  0.5976  0.7604  11.00000  0.05    0.35 
Q9    1  -0.2348  0.3831  0.6454  11.00000  0.05    0.34 
Q10   1   0.1588  0.6031  0.8771  11.00000  0.05    0.33 
;
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_7b
_database_code_depnum_ccdc_archive 'CCDC 962975'
_audit_update_record             
;
2013-09-24 deposited with the CCDC.
2014-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 N O3 S'
_chemical_formula_sum            'C15 H17 N O3 S'
_chemical_formula_weight         291.35

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   9.7309(7)
_cell_length_b                   7.3003(5)
_cell_length_c                   20.4979(14)
_cell_angle_alpha                90
_cell_angle_beta                 91.2676(10)
_cell_angle_gamma                90
_cell_volume                     1455.78(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6233
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      30.44

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.610
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.229
_shelx_estimated_absorpt_T_min   0.873
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_process_details   'SADABS v2009/1, Sheldrick, G.M., (2009)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX 2 CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16546
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.988
_diffrn_reflns_theta_max         30.560
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4425
_reflns_number_gt                3740
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX 2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0780P)²+0.1880P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'all non-H atoms found by direct methods'
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4425
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1212
_refine_ls_wR_factor_gt          0.1145
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.06427(10) 0.27105(13) 0.34288(5) 0.02176(19) Uani 1 1 d . . . . .
H1 H 0.0422(16) 0.210(2) 0.3079(8) 0.026(4) Uiso 1 1 d . . . . .
C1 C -0.03087(11) 0.40819(14) 0.36253(5) 0.0209(2) Uani 1 1 d . . . . .
C2 C -0.03676(12) 0.57621(16) 0.32392(6) 0.0237(2) Uani 1 1 d . . . . .
O1 O 0.03543(9) 0.59475(13) 0.27571(4) 0.0306(2) Uani 1 1 d . . . . .
C3 C -0.13230(14) 0.72529(17) 0.34663(7) 0.0311(3) Uani 1 1 d . . . . .
H3A H -0.1528(19) 0.798(3) 0.3093(10) 0.042(5) Uiso 1 1 d . . . . .
H3B H -0.078(2) 0.801(3) 0.3784(12) 0.060(6) Uiso 1 1 d . . . . .
C4 C -0.25353(14) 0.64888(19) 0.38270(7) 0.0325(3) Uani 1 1 d . . . . .
H4B H -0.313(2) 0.581(3) 0.3488(11) 0.057(6) Uiso 1 1 d . . . . .
H4A H -0.3096(19) 0.754(3) 0.3994(9) 0.040(4) Uiso 1 1 d . . . . .
C5 C -0.20831(12) 0.52365(16) 0.43849(6) 0.0254(2) Uani 1 1 d . . . . .
H5A H -0.2868(18) 0.462(3) 0.4533(8) 0.039(4) Uiso 1 1 d . . . . .
H5B H -0.1651(19) 0.590(3) 0.4727(10) 0.043(5) Uiso 1 1 d . . . . .
C6 C -0.10756(11) 0.38187(15) 0.41639(5) 0.0206(2) Uani 1 1 d . . . . .
S1 S -0.07921(3) 0.17938(4) 0.45973(2) 0.02774(10) Uani 1 1 d . . . . .
C14 C -0.19422(13) 0.18679(17) 0.52829(6) 0.0260(2) Uani 1 1 d . . . . .
H14A H -0.1459(16) 0.111(2) 0.5610(8) 0.031(4) Uiso 1 1 d . . . . .
H14B H -0.1961(16) 0.307(2) 0.5465(8) 0.029(4) Uiso 1 1 d . . . . .
C15 C -0.33763(15) 0.1133(2) 0.51315(8) 0.0405(3) Uani 1 1 d . . . . .
H15A H -0.3403(18) -0.018(3) 0.5008(8) 0.039(4) Uiso 1 1 d . . . . .
H15B H -0.384(2) 0.178(3) 0.4790(11) 0.053(6) Uiso 1 1 d . . . . .
H15C H -0.3956(19) 0.121(3) 0.5527(10) 0.046(5) Uiso 1 1 d . . . . .
C7 C 0.19795(11) 0.28575(15) 0.36156(5) 0.0224(2) Uani 1 1 d . . . . .
O2 O 0.23736(9) 0.41066(13) 0.39851(5) 0.0345(2) Uani 1 1 d . . . . .
C8 C 0.29475(11) 0.14437(16) 0.33854(5) 0.0229(2) Uani 1 1 d . . . . .
C9 C 0.43711(12) 0.17357(17) 0.34860(6) 0.0275(2) Uani 1 1 d . . . . .
O3 O 0.48769(10) 0.32603(14) 0.37721(6) 0.0382(2) Uani 1 1 d . . . . .
H3 H 0.420(2) 0.389(3) 0.3899(11) 0.061(6) Uiso 1 1 d . . . . .
C10 C 0.53023(13) 0.0414(2) 0.32772(6) 0.0346(3) Uani 1 1 d . . . . .
H10 H 0.637(2) 0.073(3) 0.3331(10) 0.056(6) Uiso 1 1 d . . . . .
C11 C 0.48404(15) -0.1177(2) 0.29900(7) 0.0385(3) Uani 1 1 d . . . . .
H11 H 0.5502(18) -0.206(2) 0.2867(9) 0.039(4) Uiso 1 1 d . . . . .
C12 C 0.34297(16) -0.1523(2) 0.29058(7) 0.0370(3) Uani 1 1 d . . . . .
H12 H 0.309(2) -0.282(3) 0.2741(10) 0.050(5) Uiso 1 1 d . . . . .
C13 C 0.25023(13) -0.02082(17) 0.31030(6) 0.0277(2) Uani 1 1 d . . . . .
H13 H 0.1531(17) -0.046(2) 0.3037(8) 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
N1 C7 1.3522(15) . ?
N1 C1 1.4276(14) . ?
N1 H1 0.867(17) . ?
C1 C6 1.3598(15) . ?
C1 C2 1.4603(15) . ?
C2 O1 1.2324(15) . ?
C2 C3 1.5115(17) . ?
C3 C4 1.513(2) . ?
C3 H3A 0.95(2) . ?
C3 H3B 1.00(2) . ?
C4 C5 1.5215(17) . ?
C4 H4B 1.02(2) . ?
C4 H4A 1.005(19) . ?
C5 C6 1.5024(15) . ?
C5 H5A 0.941(18) . ?
C5 H5B 0.95(2) . ?
C6 S1 1.7434(11) . ?
S1 C14 1.8167(12) . ?
C14 C15 1.5206(19) . ?
C14 H14A 0.981(17) . ?
C14 H14B 0.954(17) . ?
C15 H15A 0.990(19) . ?
C15 H15B 0.95(2) . ?
C15 H15C 0.999(19) . ?
C7 O2 1.2407(14) . ?
C7 C8 1.4814(15) . ?
C8 C13 1.4021(17) . ?
C8 C9 1.4122(16) . ?
C9 O3 1.3462(16) . ?
C9 C10 1.3974(18) . ?
O3 H3 0.85(2) . ?
C10 C11 1.373(2) . ?
C10 H10 1.06(2) . ?
C11 C12 1.403(2) . ?
C11 H11 0.950(18) . ?
C12 C13 1.3838(17) . ?
C12 H12 1.06(2) . ?
C13 H13 0.970(16) . ?

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
C7 N1 C1 119.36(9) . . ?
C7 N1 H1 119.6(10) . . ?
C1 N1 H1 116.3(10) . . ?
C6 C1 N1 120.06(9) . . ?
C6 C1 C2 122.89(10) . . ?
N1 C1 C2 117.01(10) . . ?
O1 C2 C1 120.70(11) . . ?
O1 C2 C3 122.23(11) . . ?
C1 C2 C3 117.06(10) . . ?
C2 C3 C4 112.13(11) . . ?
C2 C3 H3A 105.8(12) . . ?
C4 C3 H3A 116.6(11) . . ?
C2 C3 H3B 106.3(13) . . ?
C4 C3 H3B 107.0(13) . . ?
H3A C3 H3B 108.5(17) . . ?
C3 C4 C5 111.92(11) . . ?
C3 C4 H4B 106.4(12) . . ?
C5 C4 H4B 111.5(12) . . ?
C3 C4 H4A 108.7(11) . . ?
C5 C4 H4A 110.7(11) . . ?
H4B C4 H4A 107.5(16) . . ?
C6 C5 C4 111.54(10) . . ?
C6 C5 H5A 108.0(11) . . ?
C4 C5 H5A 107.8(11) . . ?
C6 C5 H5B 107.3(11) . . ?
C4 C5 H5B 111.4(12) . . ?
H5A C5 H5B 110.8(15) . . ?
C1 C6 C5 121.39(10) . . ?
C1 C6 S1 116.74(8) . . ?
C5 C6 S1 121.83(8) . . ?
C6 S1 C14 106.00(5) . . ?
C15 C14 S1 114.19(9) . . ?
C15 C14 H14A 111.4(10) . . ?
S1 C14 H14A 102.6(9) . . ?
C15 C14 H14B 112.2(10) . . ?
S1 C14 H14B 110.3(10) . . ?
H14A C14 H14B 105.3(14) . . ?
C14 C15 H15A 114.3(10) . . ?
C14 C15 H15B 113.3(12) . . ?
H15A C15 H15B 106.4(16) . . ?
C14 C15 H15C 110.3(11) . . ?
H15A C15 H15C 104.6(15) . . ?
H15B C15 H15C 107.3(17) . . ?
O2 C7 N1 120.90(10) . . ?
O2 C7 C8 121.09(10) . . ?
N1 C7 C8 117.97(10) . . ?
C13 C8 C9 118.89(11) . . ?
C13 C8 C7 122.54(10) . . ?
C9 C8 C7 118.49(10) . . ?
O3 C9 C10 118.11(11) . . ?
O3 C9 C8 122.43(11) . . ?
C10 C9 C8 119.46(12) . . ?
C9 O3 H3 107.3(15) . . ?
C11 C10 C9 120.47(12) . . ?
C11 C10 H10 122.4(11) . . ?
C9 C10 H10 117.1(12) . . ?
C10 C11 C12 120.99(12) . . ?
C10 C11 H11 118.1(11) . . ?
C12 C11 H11 120.8(11) . . ?
C13 C12 C11 118.83(13) . . ?
C13 C12 H12 120.9(11) . . ?
C11 C12 H12 119.9(11) . . ?
C12 C13 C8 121.30(12) . . ?
C12 C13 H13 117.8(9) . . ?
C8 C13 H13 120.9(9) . . ?

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
C7 N1 C1 C6 -95.90(13) . . . . ?
C7 N1 C1 C2 81.87(13) . . . . ?
C6 C1 C2 O1 179.43(11) . . . . ?
N1 C1 C2 O1 1.73(16) . . . . ?
C6 C1 C2 C3 0.65(16) . . . . ?
N1 C1 C2 C3 -177.05(10) . . . . ?
O1 C2 C3 C4 152.65(12) . . . . ?
C1 C2 C3 C4 -28.59(15) . . . . ?
C2 C3 C4 C5 53.49(15) . . . . ?
C3 C4 C5 C6 -50.28(15) . . . . ?
N1 C1 C6 C5 179.83(10) . . . . ?
C2 C1 C6 C5 2.19(17) . . . . ?
N1 C1 C6 S1 1.78(14) . . . . ?
C2 C1 C6 S1 -175.85(8) . . . . ?
C4 C5 C6 C1 22.88(15) . . . . ?
C4 C5 C6 S1 -159.18(9) . . . . ?
C1 C6 S1 C14 179.35(9) . . . . ?
C5 C6 S1 C14 1.32(11) . . . . ?
C6 S1 C14 C15 86.60(11) . . . . ?
C1 N1 C7 O2 4.17(16) . . . . ?
C1 N1 C7 C8 -178.05(9) . . . . ?
O2 C7 C8 C13 164.27(12) . . . . ?
N1 C7 C8 C13 -13.51(16) . . . . ?
O2 C7 C8 C9 -12.38(17) . . . . ?
N1 C7 C8 C9 169.84(10) . . . . ?
C13 C8 C9 O3 -177.94(11) . . . . ?
C7 C8 C9 O3 -1.16(17) . . . . ?
C13 C8 C9 C10 2.75(17) . . . . ?
C7 C8 C9 C10 179.52(11) . . . . ?
O3 C9 C10 C11 179.16(12) . . . . ?
C8 C9 C10 C11 -1.50(19) . . . . ?
C9 C10 C11 C12 -0.7(2) . . . . ?
C10 C11 C12 C13 1.6(2) . . . . ?
C11 C12 C13 C8 -0.3(2) . . . . ?
C9 C8 C13 C12 -1.87(18) . . . . ?
C7 C8 C13 C12 -178.51(12) . . . . ?

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 H1 O1 0.867(17) 2.039(17) 2.8987(13) 170.8(15) 2_545
C14 H14B O2 0.954(17) 2.387(17) 3.3304(15) 169.7(14) 3_566
O3 H3 O2 0.85(2) 1.79(2) 2.5599(14) 149(2) .

_refine_diff_density_max         0.752
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.064

_shelxl_version_number           2012-6

_iucr_refine_instruction_details 
; 
TITL 7b in P2(1)/c 
CELL 0.71073   9.7309   7.3003  20.4979  90.000  91.2676  90.000 
ZERR    4.00   0.0007   0.0005   0.0014   0.000   0.0010   0.000 
LATT  1 
SYMM -X, 0.5+Y, 0.5-Z 
SFAC C H N O S 
UNIT 60 68 4 12 4 
TEMP -123 
SIZE 0.16 0.23 0.61 
  
ACTA 
CONF 
WPDB -1 
  
L.S. 6 
BOND $H
FMAP 2 
PLAN 10 
EQIV $1 -x, y-1/2, -z+1/2 
EQIV $2 -x, -y+1, -z+1 
HTAB N1 O1_$1 
HTAB C14 O2_$2 
HTAB O3 O2 
  
MPLA C8 > C13 
MPLA N1 C1 C2 C3 C5 C6 
  
REM  EXTI    0.000000   insig. 
WGHT    0.078000    0.188000 
FVAR       0.19647 
N1    3    0.064266    0.271053    0.342883    11.00000    0.02347    0.02167 = 
         0.02016   -0.00285    0.00060    0.00375 
H1    2    0.042191    0.209921    0.307928    11.00000    0.02561 
C1    1   -0.030870    0.408187    0.362530    11.00000    0.02243    0.01966 = 
         0.02057   -0.00074   -0.00170    0.00294 
C2    1   -0.036759    0.576210    0.323916    11.00000    0.02454    0.02348 = 
         0.02285    0.00251   -0.00468   -0.00025 
O1    4    0.035427    0.594745    0.275709    11.00000    0.03086    0.03384 = 
         0.02708    0.00775    0.00100    0.00130 
C3    1   -0.132298    0.725293    0.346628    11.00000    0.03501    0.02258 = 
         0.03575    0.00505    0.00146    0.00656 
H3A   2   -0.152787    0.797542    0.309283    11.00000    0.04182 
H3B   2   -0.077942    0.801224    0.378445    11.00000    0.05993 
C4    1   -0.253528    0.648877    0.382700    11.00000    0.03190    0.03014 = 
         0.03539    0.00279   -0.00109    0.00851 
H4B   2   -0.312756    0.580552    0.348819    11.00000    0.05707 
H4A   2   -0.309636    0.753856    0.399353    11.00000    0.04039 
C5    1   -0.208307    0.523654    0.438491    11.00000    0.02600    0.02334 = 
         0.02681    0.00029    0.00192    0.00676 
H5A   2   -0.286765    0.462400    0.453326    11.00000    0.03852 
H5B   2   -0.165112    0.590462    0.472730    11.00000    0.04286 
C6    1   -0.107563    0.381866    0.416390    11.00000    0.02172    0.01900 = 
         0.02108   -0.00049   -0.00250    0.00230 
S1    5   -0.079212    0.179380    0.459726    11.00000    0.03344    0.02237 = 
         0.02772    0.00555    0.00761    0.00815 
C14   1   -0.194222    0.186793    0.528291    11.00000    0.02906    0.02784 = 
         0.02119    0.00293    0.00282    0.00204 
H14A  2   -0.145871    0.111122    0.561002    11.00000    0.03133 
H14B  2   -0.196138    0.307090    0.546486    11.00000    0.02862 
C15   1   -0.337628    0.113301    0.513149    11.00000    0.03433    0.05149 = 
         0.03574    0.01044   -0.00041   -0.00892 
H15A  2   -0.340279   -0.017828    0.500835    11.00000    0.03908 
H15B  2   -0.384360    0.178029    0.478988    11.00000    0.05274 
H15C  2   -0.395637    0.121369    0.552658    11.00000    0.04565 
C7    1    0.197954    0.285750    0.361561    11.00000    0.02480    0.02232 = 
         0.02016    0.00042    0.00056    0.00233 
O2    4    0.237362    0.410658    0.398513    11.00000    0.03108    0.03287 = 
         0.03923   -0.01372   -0.00696    0.00369 
C8    1    0.294750    0.144373    0.338545    11.00000    0.02357    0.02558 = 
         0.01947    0.00162    0.00158    0.00463 
C9    1    0.437114    0.173567    0.348599    11.00000    0.02496    0.03382 = 
         0.02388    0.00569    0.00096    0.00253 
O3    4    0.487689    0.326030    0.377208    11.00000    0.02610    0.03852 = 
         0.04960   -0.00159   -0.00444   -0.00215 
H3    2    0.419576    0.388740    0.389852    11.00000    0.06092 
C10   1    0.530234    0.041381    0.327719    11.00000    0.02713    0.04757 = 
         0.02926    0.00687    0.00363    0.01059 
H10   2    0.636660    0.072769    0.333143    11.00000    0.05639 
C11   1    0.484044   -0.117724    0.298998    11.00000    0.03887    0.04825 = 
         0.02846   -0.00190    0.00138    0.02239 
H11   2    0.550197   -0.206234    0.286733    11.00000    0.03873 
C12   1    0.342970   -0.152265    0.290581    11.00000    0.04273    0.03516 = 
         0.03280   -0.00853   -0.00477    0.01596 
H12   2    0.309005   -0.282112    0.274148    11.00000    0.04984 
C13   1    0.250229   -0.020817    0.310303    11.00000    0.03006    0.02745 = 
         0.02556   -0.00241   -0.00107    0.00617 
H13   2    0.153108   -0.046340    0.303703    11.00000    0.02861 
HKLF 4 
  
REM  7b in P2(1)/c 
REM R1 =  0.0418 for    3740 Fo > 4sig(Fo)  and  0.0495 for all    4425 data 
REM    249 parameters refined using      0 restraints 
  
END 
  
WGHT      0.0780      0.1870 
  
REM Highest difference peak  0.752,  deepest hole -0.236,  1-sigma level  0.064 
Q1    1  -0.1823  0.7087  0.4059  11.00000  0.05    0.75 
Q2    1  -0.0374  0.4852  0.3409  11.00000  0.05    0.47 
Q3    1  -0.0664  0.4003  0.3895  11.00000  0.05    0.44 
Q4    1   0.2435  0.2079  0.3518  11.00000  0.05    0.42 
Q5    1  -0.0943  0.2783  0.4346  11.00000  0.05    0.42 
Q6    1   0.2798  0.0629  0.3216  11.00000  0.05    0.39 
Q7    1  -0.1305  0.1901  0.4921  11.00000  0.05    0.38 
Q8    1   0.0152  0.3382  0.3537  11.00000  0.05    0.37 
Q9    1   0.3604  0.1557  0.3455  11.00000  0.05    0.37 
Q10   1   0.4125 -0.1075  0.2904  11.00000  0.05    0.36 
;

#===END
