# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound_beta-25
_database_code_depnum_ccdc_archive 'CCDC 1530225'
_audit_update_record             
;
2017-01-30 deposited with the CCDC.
2017-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'rac-(3S,5aR,6S,9S,9aS,10R)-methyl 10-bromo-1-oxo-3,4,5,5a,6,9-hexahydro-1H-6,9-ethano-3,9a-methanobenzo[c]oxepine-7-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 Br O4'
_chemical_formula_sum            'C15 H17 Br O4'
_chemical_formula_weight         341.20


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

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

_cell_length_a                   16.036(3)
_cell_length_b                   7.932(2)
_cell_length_c                   22.399(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.857(11)
_cell_angle_gamma                90
_cell_volume                     2788.3(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3328
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      27.485

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392
_exptl_absorpt_coefficient_mu    2.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_correction_T_max  0.54
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Nonius Kappa CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18544
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.865
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3185
_reflns_number_gt                2485
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Nonius, 1998);Denzo (Otwinowski, Z. & Minor, W., 1997)'
_computing_cell_refinement       'Denzo (Otwinowski, Z. & Minor, W., 1997)'
_computing_data_reduction        'Scalepack (Otwinowski, Z. & Minor, W., 1997)'
_computing_structure_solution    'SIR97 (Altomare et al, 1999)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    'MERCURY (Macrae, 2006)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_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     
'w=1/[σ²(Fo²)+(0.0434P)²+2.2037P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3185
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0878
_refine_ls_wR_factor_gt          0.0797
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C5(H5), C4(H4), C1(H1), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
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
Br1 Br 0.48479(2) -0.20578(4) 0.36944(2) 0.05850(12) Uani 1 1 d . . . . .
O1 O 0.28275(12) -0.0583(2) 0.23630(7) 0.0605(5) Uani 1 1 d . . . . .
O2 O 0.17242(11) 0.0063(2) 0.27844(10) 0.0677(5) Uani 1 1 d . . . . .
O3 O 0.27404(13) 0.5773(2) 0.41794(10) 0.0677(5) Uani 1 1 d . . . . .
O4 O 0.15572(11) 0.4362(2) 0.42446(10) 0.0665(5) Uani 1 1 d . . . . .
C1 C 0.28361(14) -0.0184(3) 0.40031(10) 0.0394(5) Uani 1 1 d . . . . .
H1 H 0.2507 -0.1222 0.4010 0.047 Uiso 1 1 calc R U . . .
C2 C 0.23093(14) 0.1348(3) 0.40632(10) 0.0424(5) Uani 1 1 d . . . . .
H2 H 0.1737 0.1283 0.4085 0.051 Uiso 1 1 calc R U . . .
C3 C 0.27251(14) 0.2805(3) 0.40829(10) 0.0407(5) Uani 1 1 d . . . . .
C4 C 0.36273(14) 0.2644(3) 0.39926(10) 0.0417(5) Uani 1 1 d . . . . .
H4 H 0.3900 0.3751 0.3997 0.050 Uiso 1 1 calc R U . . .
C5 C 0.35601(13) 0.1768(3) 0.33690(10) 0.0377(5) Uani 1 1 d . . . . .
H5 H 0.3138 0.2404 0.3076 0.045 Uiso 1 1 calc R U . . .
C6 C 0.43754(17) 0.1725(3) 0.31111(12) 0.0523(6) Uani 1 1 d . . . . .
H6A H 0.4510 0.2857 0.2998 0.063 Uiso 1 1 calc R U . . .
H6B H 0.4845 0.1329 0.3424 0.063 Uiso 1 1 calc R U . . .
C7 C 0.42788(19) 0.0570(4) 0.25522(12) 0.0637(7) Uani 1 1 d . . . . .
H7A H 0.4026 0.1208 0.2191 0.076 Uiso 1 1 calc R U . . .
H7B H 0.4840 0.0207 0.2506 0.076 Uiso 1 1 calc R U . . .
C8 C 0.37345(17) -0.0975(4) 0.25922(11) 0.0534(6) Uani 1 1 d . . . . .
H8 H 0.3913 -0.1920 0.2366 0.064 Uiso 1 1 calc R U . . .
C9 C 0.37120(13) -0.1495(3) 0.32414(10) 0.0401(5) Uani 1 1 d . . . . .
H9 H 0.3366 -0.2520 0.3217 0.048 Uiso 1 1 calc R U . . .
C10 C 0.31736(12) -0.0039(3) 0.34136(9) 0.0341(4) Uani 1 1 d . . . . .
C11 C 0.35983(17) -0.0097(3) 0.45528(10) 0.0518(6) Uani 1 1 d . . . . .
H11A H 0.3392 -0.0084 0.4930 0.062 Uiso 1 1 calc R U . . .
H11B H 0.3957 -0.1083 0.4555 0.062 Uiso 1 1 calc R U . . .
C12 C 0.41165(16) 0.1502(4) 0.45053(11) 0.0531(6) Uani 1 1 d . . . . .
H12A H 0.4665 0.1201 0.4418 0.064 Uiso 1 1 calc R U . . .
H12B H 0.4215 0.2105 0.4890 0.064 Uiso 1 1 calc R U . . .
C13 C 0.23601(15) 0.4472(3) 0.41683(10) 0.0453(5) Uani 1 1 d . . . . .
C14 C 0.1142(2) 0.5929(4) 0.43301(18) 0.0808(10) Uani 1 1 d . . . . .
H14A H 0.1491 0.6555 0.4655 0.121 Uiso 1 1 calc R U . . .
H14B H 0.0600 0.5700 0.4432 0.121 Uiso 1 1 calc R U . . .
H14C H 0.1058 0.6576 0.3960 0.121 Uiso 1 1 calc R U . . .
C15 C 0.24747(15) -0.0173(3) 0.28433(11) 0.0481(6) Uani 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
Br1 C9 1.946(2) . ?
O1 C15 1.354(3) . ?
O1 C8 1.473(3) . ?
O2 C15 1.198(3) . ?
O3 C13 1.197(3) . ?
O4 C13 1.336(3) . ?
O4 C14 1.442(3) . ?
C1 C2 1.501(3) . ?
C1 C10 1.531(3) . ?
C1 C11 1.548(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.330(3) . ?
C2 H2 0.9300 . ?
C3 C13 1.474(3) . ?
C3 C4 1.507(3) . ?
C4 C5 1.544(3) . ?
C4 C12 1.544(3) . ?
C4 H4 0.9800 . ?
C5 C6 1.534(3) . ?
C5 C10 1.573(3) . ?
C5 H5 0.9800 . ?
C6 C7 1.533(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.517(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.519(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.538(3) . ?
C9 H9 0.9800 . ?
C10 C15 1.520(3) . ?
C11 C12 1.532(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C15 O1 C8 108.52(17) . . ?
C13 O4 C14 116.4(2) . . ?
C2 C1 C10 108.76(17) . . ?
C2 C1 C11 105.05(19) . . ?
C10 C1 C11 108.75(17) . . ?
C2 C1 H1 111.3 . . ?
C10 C1 H1 111.3 . . ?
C11 C1 H1 111.3 . . ?
C3 C2 C1 114.74(19) . . ?
C3 C2 H2 122.6 . . ?
C1 C2 H2 122.6 . . ?
C2 C3 C13 125.0(2) . . ?
C2 C3 C4 114.2(2) . . ?
C13 C3 C4 120.8(2) . . ?
C3 C4 C5 105.62(18) . . ?
C3 C4 C12 107.76(19) . . ?
C5 C4 C12 109.86(19) . . ?
C3 C4 H4 111.1 . . ?
C5 C4 H4 111.1 . . ?
C12 C4 H4 111.1 . . ?
C6 C5 C4 116.38(19) . . ?
C6 C5 C10 112.38(18) . . ?
C4 C5 C10 107.91(17) . . ?
C6 C5 H5 106.5 . . ?
C4 C5 H5 106.5 . . ?
C10 C5 H5 106.5 . . ?
C7 C6 C5 111.7(2) . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C6 113.4(2) . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
O1 C8 C7 110.4(2) . . ?
O1 C8 C9 100.07(18) . . ?
C7 C8 C9 113.7(2) . . ?
O1 C8 H8 110.7 . . ?
C7 C8 H8 110.7 . . ?
C9 C8 H8 110.7 . . ?
C8 C9 C10 99.28(19) . . ?
C8 C9 Br1 110.95(16) . . ?
C10 C9 Br1 123.73(14) . . ?
C8 C9 H9 107.3 . . ?
C10 C9 H9 107.3 . . ?
Br1 C9 H9 107.3 . . ?
C15 C10 C1 112.91(18) . . ?
C15 C10 C9 95.25(17) . . ?
C1 C10 C9 118.43(17) . . ?
C15 C10 C5 104.05(16) . . ?
C1 C10 C5 109.70(17) . . ?
C9 C10 C5 114.81(17) . . ?
C12 C11 C1 109.41(18) . . ?
C12 C11 H11A 109.8 . . ?
C1 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
C1 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
C11 C12 C4 109.71(19) . . ?
C11 C12 H12A 109.7 . . ?
C4 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
C4 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
O3 C13 O4 123.7(2) . . ?
O3 C13 C3 124.2(2) . . ?
O4 C13 C3 112.1(2) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 O1 121.6(2) . . ?
O2 C15 C10 129.2(2) . . ?
O1 C15 C10 109.16(19) . . ?

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
C10 C1 C2 C3 -59.6(3) . . . . ?
C11 C1 C2 C3 56.7(3) . . . . ?
C1 C2 C3 C13 -177.1(2) . . . . ?
C1 C2 C3 C4 4.4(3) . . . . ?
C2 C3 C4 C5 57.5(3) . . . . ?
C13 C3 C4 C5 -121.1(2) . . . . ?
C2 C3 C4 C12 -59.9(3) . . . . ?
C13 C3 C4 C12 121.5(2) . . . . ?
C3 C4 C5 C6 169.61(19) . . . . ?
C12 C4 C5 C6 -74.4(2) . . . . ?
C3 C4 C5 C10 -63.0(2) . . . . ?
C12 C4 C5 C10 52.9(2) . . . . ?
C4 C5 C6 C7 170.0(2) . . . . ?
C10 C5 C6 C7 44.9(3) . . . . ?
C5 C6 C7 C8 -35.3(3) . . . . ?
C15 O1 C8 C7 -95.3(2) . . . . ?
C15 O1 C8 C9 24.9(2) . . . . ?
C6 C7 C8 O1 86.5(3) . . . . ?
C6 C7 C8 C9 -25.1(3) . . . . ?
O1 C8 C9 C10 -46.9(2) . . . . ?
C7 C8 C9 C10 70.8(2) . . . . ?
O1 C8 C9 Br1 -178.54(15) . . . . ?
C7 C8 C9 Br1 -60.9(3) . . . . ?
C2 C1 C10 C15 -68.2(2) . . . . ?
C11 C1 C10 C15 177.93(18) . . . . ?
C2 C1 C10 C9 -178.16(18) . . . . ?
C11 C1 C10 C9 67.9(2) . . . . ?
C2 C1 C10 C5 47.4(2) . . . . ?
C11 C1 C10 C5 -66.5(2) . . . . ?
C8 C9 C10 C15 49.24(19) . . . . ?
Br1 C9 C10 C15 172.25(16) . . . . ?
C8 C9 C10 C1 168.86(18) . . . . ?
Br1 C9 C10 C1 -68.1(2) . . . . ?
C8 C9 C10 C5 -58.9(2) . . . . ?
Br1 C9 C10 C5 64.1(2) . . . . ?
C6 C5 C10 C15 -98.2(2) . . . . ?
C4 C5 C10 C15 132.17(19) . . . . ?
C6 C5 C10 C1 140.76(19) . . . . ?
C4 C5 C10 C1 11.1(2) . . . . ?
C6 C5 C10 C9 4.5(3) . . . . ?
C4 C5 C10 C9 -125.15(19) . . . . ?
C2 C1 C11 C12 -62.0(2) . . . . ?
C10 C1 C11 C12 54.3(2) . . . . ?
C1 C11 C12 C4 9.7(3) . . . . ?
C3 C4 C12 C11 48.7(2) . . . . ?
C5 C4 C12 C11 -65.9(2) . . . . ?
C14 O4 C13 O3 1.5(4) . . . . ?
C14 O4 C13 C3 -179.8(2) . . . . ?
C2 C3 C13 O3 -179.3(3) . . . . ?
C4 C3 C13 O3 -0.9(4) . . . . ?
C2 C3 C13 O4 2.0(3) . . . . ?
C4 C3 C13 O4 -179.6(2) . . . . ?
C8 O1 C15 O2 -173.7(2) . . . . ?
C8 O1 C15 C10 7.9(3) . . . . ?
C1 C10 C15 O2 21.5(3) . . . . ?
C9 C10 C15 O2 145.4(3) . . . . ?
C5 C10 C15 O2 -97.4(3) . . . . ?
C1 C10 C15 O1 -160.27(18) . . . . ?
C9 C10 C15 O1 -36.4(2) . . . . ?
C5 C10 C15 O1 80.8(2) . . . . ?

_refine_diff_density_max         0.271
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.055






_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hot ethyl acetate'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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data_compound_12
_database_code_depnum_ccdc_archive 'CCDC 1530223'
_audit_update_record             
;
2017-01-30 deposited with the CCDC.
2017-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 Cs O4, 2 (H2 O)'
_chemical_formula_sum            'C15 H21 Cs O6'
_chemical_formula_weight         430.23

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'
Cs Cs -0.3680 2.1192 '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/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                   18.318(1)
_cell_length_b                   7.395(1)
_cell_length_c                   12.871(1)
_cell_angle_alpha                90
_cell_angle_beta                 108.64(5)
_cell_angle_gamma                90
_cell_volume                     1652.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3215
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      25.350

_exptl_crystal_description       tab
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    2.266
_shelx_estimated_absorpt_T_min   0.805
_shelx_estimated_absorpt_T_max   0.805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.82
_exptl_absorpt_process_details   Scalepack
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Enraf-Nonius KappaCCD'
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_detector_area_resol_mean 9
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_reflns_number            17586
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.994
_diffrn_reflns_theta_max         25.328
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2998
_reflns_number_gt                2456
_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       
'COLLECT (Hooft, 1998); DENZO(Otwinowski, Z. & Minor, W., 1997)'
_computing_cell_refinement       'DENZO(Otwinowski, Z. & Minor, W., 1997)'
_computing_data_reduction        'SCALEPACK(Otwinowski, Z. & Minor, W., 1997)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0829P)²+9.2497P] 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         2984
_refine_ls_number_parameters     212
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1835
_refine_ls_wR_factor_gt          0.1755
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.103
_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
Cs1 Cs 0.44111(3) 0.32922(9) 0.31742(5) 0.0698(3) Uani 1 1 d . . . . .
O1 O 0.2694(3) -0.6925(7) 0.1923(4) 0.0496(13) Uani 1 1 d . . . . .
C1 C 0.1657(3) -0.4715(8) 0.1413(4) 0.0295(12) Uani 1 1 d . . . . .
C10 C 0.1635(4) -0.2970(9) 0.0722(5) 0.0365(14) Uani 1 1 d . . . . .
H10 H 0.1449 -0.3237 -0.0065 0.044 Uiso 1 1 calc R U . . .
C9 C 0.1114(5) -0.1585(10) 0.1026(6) 0.0450(16) Uani 1 1 d . . . . .
H9A H 0.0624 -0.2138 0.0974 0.054 Uiso 1 1 calc R U . . .
H9B H 0.1018 -0.0573 0.0521 0.054 Uiso 1 1 calc R U . . .
C8 C 0.1513(4) -0.0907(10) 0.2214(6) 0.0457(16) Uani 1 1 d . . . . .
H8A H 0.1705 0.0313 0.2202 0.055 Uiso 1 1 calc R U . . .
H8B H 0.1148 -0.0895 0.2619 0.055 Uiso 1 1 calc R U . . .
C12 C 0.2754(4) -0.1920(9) 0.2137(6) 0.0392(15) Uani 1 1 d . . . . .
C14 C 0.2252(4) -0.6020(9) 0.1220(5) 0.0336(13) Uani 1 1 d . . . . .
C2 C 0.0903(4) -0.5778(10) 0.0997(5) 0.0400(14) Uani 1 1 d . . . . .
H2 H 0.0669 -0.5884 0.0243 0.048 Uiso 1 1 calc R U . . .
O2 O 0.2208(3) -0.6104(7) 0.0169(4) 0.0464(12) Uani 1 1 d . . . . .
C11 C 0.2445(4) -0.2281(9) 0.1067(5) 0.0390(14) Uani 1 1 d . . . . .
H11 H 0.2714 -0.2114 0.0572 0.047 Uiso 1 1 calc R U . . .
C6 C 0.1898(4) -0.4186(9) 0.2643(5) 0.0334(13) Uani 1 1 d . . . . .
H6 H 0.2334 -0.4955 0.3039 0.040 Uiso 1 1 calc R U . . .
C4 C 0.0862(4) -0.6309(11) 0.2864(6) 0.0481(17) Uani 1 1 d . . . . .
H4A H 0.1225 -0.7264 0.3193 0.058 Uiso 1 1 calc R U . . .
H4B H 0.0435 -0.6389 0.3155 0.058 Uiso 1 1 calc R U . . .
O4 O 0.3812(4) -0.1087(11) 0.3683(5) 0.0729(18) Uani 1 1 d D . . . .
C15 C 0.2761(5) -0.7300(13) -0.0081(7) 0.059(2) Uani 1 1 d . . . . .
H15A H 0.2731 -0.7149 -0.0834 0.089 Uiso 1 1 calc R U . . .
H15B H 0.2646 -0.8532 0.0043 0.089 Uiso 1 1 calc R U . . .
H15C H 0.3272 -0.7007 0.0384 0.089 Uiso 1 1 calc R U . . .
C5 C 0.1252(4) -0.4486(10) 0.3149(6) 0.0461(16) Uani 1 1 d . . . . .
H5A H 0.1467 -0.4384 0.3940 0.055 Uiso 1 1 calc R U . . .
H5B H 0.0869 -0.3542 0.2895 0.055 Uiso 1 1 calc R U . . .
O5W O 0.5452(5) -0.0433(17) 0.4112(7) 0.129(4) Uani 1 1 d D . . . .
H5W1 H 0.5004(10) -0.078(8) 0.401(9) 0.194 Uiso 1 1 d D U . . .
H5W2 H 0.564(7) -0.02(2) 0.478(3) 0.194 Uiso 1 1 d D U . . .
O6W O 0.3932(4) 0.5650(10) 0.4873(6) 0.0731(17) Uani 1 1 d D . . . .
H6W1 H 0.393(6) 0.574(13) 0.552(2) 0.110 Uiso 1 1 d D U . . .
H6W2 H 0.370(5) 0.655(7) 0.454(5) 0.110 Uiso 1 1 d D U . . .
C13 C 0.3555(4) -0.1238(11) 0.2654(6) 0.0478(17) Uani 1 1 d . . . . .
O3 O 0.3942(3) -0.0815(10) 0.2047(5) 0.0648(16) Uani 1 1 d . . . . .
C3 C 0.0571(4) -0.6543(10) 0.1640(6) 0.0450(17) Uani 1 1 d . . . . .
H3 H 0.0139 -0.7259 0.1330 0.054 Uiso 1 1 calc R U . . .
C7 C 0.2184(4) -0.2197(10) 0.2766(5) 0.0394(15) Uani 1 1 d . . . . .
H7 H 0.2421 -0.1885 0.3541 0.047 Uiso 1 1 calc R U . . .


_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
Cs1 O1 3.046(6) 1_565 ?
Cs1 O6W 3.134(6) . ?
Cs1 O5W 3.175(9) 2_655 ?
Cs1 O3 3.187(6) 2_655 ?
Cs1 O5W 3.348(12) . ?
Cs1 O6W 3.356(8) 3_666 ?
Cs1 O3 3.357(7) . ?
Cs1 O4 3.547(7) . ?
Cs1 C13 3.669(8) . ?
Cs1 Cs1 4.8714(11) 2_655 ?
Cs1 Cs1 4.8714(11) 2_645 ?
Cs1 Cs1 5.162(2) 3_666 ?
Cs1 H5W1 3.27(6) . ?
O1 C14 1.206(8) . ?
O1 Cs1 3.046(6) 1_545 ?
C1 C2 1.529(9) . ?
C1 C14 1.534(9) . ?
C1 C6 1.551(8) . ?
C1 C10 1.560(8) . ?
C10 C11 1.495(10) . ?
C10 C9 1.533(9) . ?
C10 H10 0.9800 . ?
C9 C8 1.552(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C8 C7 1.539(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C12 C11 1.339(10) . ?
C12 C13 1.492(10) . ?
C12 C7 1.526(9) . ?
C14 O2 1.331(8) . ?
C2 C3 1.302(10) . ?
C2 H2 0.9300 . ?
O2 C15 1.457(9) . ?
C11 H11 0.9300 . ?
C6 C5 1.538(9) . ?
C6 C7 1.552(10) . ?
C6 H6 0.9800 . ?
C4 C3 1.504(10) . ?
C4 C5 1.515(11) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
O4 C13 1.261(9) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
O5W Cs1 3.175(9) 2_645 ?
O5W H5W1 0.830(2) . ?
O5W H5W2 0.830(2) . ?
O6W Cs1 3.356(8) 3_666 ?
O6W H6W1 0.830(2) . ?
O6W H6W2 0.830(2) . ?
C13 O3 1.252(9) . ?
O3 Cs1 3.188(6) 2_645 ?
C3 H3 0.9300 . ?
C7 H7 0.9800 . ?

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
O1 Cs1 O6W 85.75(16) 1_565 . ?
O1 Cs1 O5W 84.24(19) 1_565 2_655 ?
O6W Cs1 O5W 127.2(3) . 2_655 ?
O1 Cs1 O3 144.15(14) 1_565 2_655 ?
O6W Cs1 O3 115.55(18) . 2_655 ?
O5W Cs1 O3 59.9(2) 2_655 2_655 ?
O1 Cs1 O5W 121.3(2) 1_565 . ?
O6W Cs1 O5W 117.4(2) . . ?
O5W Cs1 O5W 112.0(2) 2_655 . ?
O3 Cs1 O5W 75.9(2) 2_655 . ?
O1 Cs1 O6W 160.44(14) 1_565 3_666 ?
O6W Cs1 O6W 74.69(19) . 3_666 ?
O5W Cs1 O6W 107.7(2) 2_655 3_666 ?
O3 Cs1 O6W 50.47(15) 2_655 3_666 ?
O5W Cs1 O6W 69.3(2) . 3_666 ?
O1 Cs1 O3 69.24(14) 1_565 . ?
O6W Cs1 O3 135.64(16) . . ?
O5W Cs1 O3 87.3(3) 2_655 . ?
O3 Cs1 O3 105.50(16) 2_655 . ?
O5W Cs1 O3 56.57(19) . . ?
O6W Cs1 O3 125.42(16) 3_666 . ?
O1 Cs1 O4 73.80(14) 1_565 . ?
O6W Cs1 O4 101.93(18) . . ?
O5W Cs1 O4 124.3(3) 2_655 . ?
O3 Cs1 O4 124.27(17) 2_655 . ?
O5W Cs1 O4 50.0(2) . . ?
O6W Cs1 O4 109.49(16) 3_666 . ?
O3 Cs1 O4 37.10(14) . . ?
O1 Cs1 C13 63.03(16) 1_565 . ?
O6W Cs1 C13 115.89(18) . . ?
O5W Cs1 C13 104.9(3) 2_655 . ?
O3 Cs1 C13 122.28(18) 2_655 . ?
O5W Cs1 C13 58.4(2) . . ?
O6W Cs1 C13 125.51(18) 3_666 . ?
O3 Cs1 C13 19.89(15) . . ?
O4 Cs1 C13 20.03(15) . . ?
O1 Cs1 Cs1 110.60(10) 1_565 2_655 ?
O6W Cs1 Cs1 94.65(14) . 2_655 ?
O5W Cs1 Cs1 43.1(2) 2_655 2_655 ?
O3 Cs1 Cs1 43.25(12) 2_655 2_655 ?
O5W Cs1 Cs1 119.13(18) . 2_655 ?
O6W Cs1 Cs1 72.08(13) 3_666 2_655 ?
O3 Cs1 Cs1 127.87(9) . 2_655 ?
O4 Cs1 Cs1 163.19(11) . 2_655 ?
C13 Cs1 Cs1 147.16(12) . 2_655 ?
O1 Cs1 Cs1 105.77(10) 1_565 2_645 ?
O6W Cs1 Cs1 157.77(14) . 2_645 ?
O5W Cs1 Cs1 73.8(2) 2_655 2_645 ?
O3 Cs1 Cs1 65.54(13) 2_655 2_645 ?
O5W Cs1 Cs1 40.35(15) . 2_645 ?
O6W Cs1 Cs1 92.64(11) 3_666 2_645 ?
O3 Cs1 Cs1 40.58(9) . 2_645 ?
O4 Cs1 Cs1 64.62(12) . 2_645 ?
C13 Cs1 Cs1 56.90(12) . 2_645 ?
Cs1 Cs1 Cs1 98.75(3) 2_655 2_645 ?
O1 Cs1 Cs1 124.59(10) 1_565 3_666 ?
O6W Cs1 Cs1 38.84(13) . 3_666 ?
O5W Cs1 Cs1 124.4(2) 2_655 3_666 ?
O3 Cs1 Cs1 81.25(12) 2_655 3_666 ?
O5W Cs1 Cs1 92.88(15) . 3_666 ?
O6W Cs1 Cs1 35.85(11) 3_666 3_666 ?
O3 Cs1 Cs1 144.19(11) . 3_666 ?
O4 Cs1 Cs1 110.03(9) . 3_666 ?
C13 Cs1 Cs1 130.00(12) . 3_666 ?
Cs1 Cs1 Cs1 81.326(19) 2_655 3_666 ?
Cs1 Cs1 Cs1 126.30(3) 2_645 3_666 ?
O1 Cs1 H5W1 107.7(6) 1_565 . ?
O6W Cs1 H5W1 115(2) . . ?
O5W Cs1 H5W1 117.7(19) 2_655 . ?
O3 Cs1 H5W1 89.8(6) 2_655 . ?
O5W Cs1 H5W1 14.35(6) . . ?
O6W Cs1 H5W1 80.9(12) 3_666 . ?
O3 Cs1 H5W1 47.2(17) . . ?
O4 Cs1 H5W1 35.61(18) . . ?
C13 Cs1 H5W1 45.3(9) . . ?
Cs1 Cs1 H5W1 132.8(7) 2_655 . ?
Cs1 Cs1 H5W1 43.9(19) 2_645 . ?
Cs1 Cs1 H5W1 98.7(19) 3_666 . ?
C14 O1 Cs1 134.4(5) . 1_545 ?
C2 C1 C14 103.2(5) . . ?
C2 C1 C6 114.7(5) . . ?
C14 C1 C6 109.8(5) . . ?
C2 C1 C10 111.7(5) . . ?
C14 C1 C10 108.6(5) . . ?
C6 C1 C10 108.7(5) . . ?
C11 C10 C9 109.6(6) . . ?
C11 C10 C1 105.7(5) . . ?
C9 C10 C1 108.2(5) . . ?
C11 C10 H10 111.1 . . ?
C9 C10 H10 111.1 . . ?
C1 C10 H10 111.1 . . ?
C10 C9 C8 109.4(6) . . ?
C10 C9 H9A 109.8 . . ?
C8 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
C7 C8 C9 108.0(5) . . ?
C7 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 . . ?
C7 C8 H8B 110.1 . . ?
C9 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C11 C12 C13 124.0(6) . . ?
C11 C12 C7 112.5(6) . . ?
C13 C12 C7 123.5(6) . . ?
O1 C14 O2 123.0(6) . . ?
O1 C14 C1 124.7(6) . . ?
O2 C14 C1 112.3(5) . . ?
C3 C2 C1 123.6(6) . . ?
C3 C2 H2 118.2 . . ?
C1 C2 H2 118.2 . . ?
C14 O2 C15 115.6(6) . . ?
C12 C11 C10 115.3(6) . . ?
C12 C11 H11 122.4 . . ?
C10 C11 H11 122.4 . . ?
C5 C6 C1 112.9(5) . . ?
C5 C6 C7 111.9(5) . . ?
C1 C6 C7 108.7(5) . . ?
C5 C6 H6 107.7 . . ?
C1 C6 H6 107.7 . . ?
C7 C6 H6 107.7 . . ?
C3 C4 C5 109.7(6) . . ?
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 . . ?
C13 O4 Cs1 85.4(5) . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C5 C6 113.2(6) . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C6 C5 H5B 108.9 . . ?
H5A C5 H5B 107.8 . . ?
Cs1 O5W Cs1 96.6(3) 2_645 . ?
Cs1 O5W H5W1 98(8) 2_645 . ?
Cs1 O5W H5W1 77(4) . . ?
Cs1 O5W H5W2 152(10) 2_645 . ?
Cs1 O5W H5W2 103(10) . . ?
H5W1 O5W H5W2 106.5(6) . . ?
Cs1 O6W Cs1 105.31(19) . 3_666 ?
Cs1 O6W H6W1 146(6) . . ?
Cs1 O6W H6W1 61(8) 3_666 . ?
Cs1 O6W H6W2 108(6) . . ?
Cs1 O6W H6W2 113(7) 3_666 . ?
H6W1 O6W H6W2 106.5(6) . . ?
O3 C13 O4 122.6(7) . . ?
O3 C13 C12 118.6(7) . . ?
O4 C13 C12 118.8(7) . . ?
O3 C13 Cs1 65.9(5) . . ?
O4 C13 Cs1 74.5(5) . . ?
C12 C13 Cs1 133.8(5) . . ?
C13 O3 Cs1 138.2(5) . 2_645 ?
C13 O3 Cs1 94.2(5) . . ?
Cs1 O3 Cs1 96.16(15) 2_645 . ?
C2 C3 C4 122.4(7) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C12 C7 C8 104.7(5) . . ?
C12 C7 C6 109.8(5) . . ?
C8 C7 C6 110.3(6) . . ?
C12 C7 H7 110.6 . . ?
C8 C7 H7 110.6 . . ?
C6 C7 H7 110.6 . . ?

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
C2 C1 C10 C11 -169.0(5) . . . . ?
C14 C1 C10 C11 -55.9(6) . . . . ?
C6 C1 C10 C11 63.5(6) . . . . ?
C2 C1 C10 C9 73.7(7) . . . . ?
C14 C1 C10 C9 -173.2(5) . . . . ?
C6 C1 C10 C9 -53.8(7) . . . . ?
C11 C10 C9 C8 -45.4(7) . . . . ?
C1 C10 C9 C8 69.3(7) . . . . ?
C10 C9 C8 C7 -14.2(8) . . . . ?
Cs1 O1 C14 O2 78.0(8) 1_545 . . . ?
Cs1 O1 C14 C1 -104.8(7) 1_545 . . . ?
C2 C1 C14 O1 -101.7(7) . . . . ?
C6 C1 C14 O1 21.0(9) . . . . ?
C10 C1 C14 O1 139.7(6) . . . . ?
C2 C1 C14 O2 75.8(6) . . . . ?
C6 C1 C14 O2 -161.5(5) . . . . ?
C10 C1 C14 O2 -42.8(7) . . . . ?
C14 C1 C2 C3 104.5(7) . . . . ?
C6 C1 C2 C3 -14.8(9) . . . . ?
C10 C1 C2 C3 -139.1(7) . . . . ?
O1 C14 O2 C15 -3.2(10) . . . . ?
C1 C14 O2 C15 179.3(6) . . . . ?
C13 C12 C11 C10 179.4(6) . . . . ?
C7 C12 C11 C10 -3.3(9) . . . . ?
C9 C10 C11 C12 58.4(8) . . . . ?
C1 C10 C11 C12 -57.9(7) . . . . ?
C2 C1 C6 C5 -11.9(8) . . . . ?
C14 C1 C6 C5 -127.5(6) . . . . ?
C10 C1 C6 C5 113.9(6) . . . . ?
C2 C1 C6 C7 -136.7(6) . . . . ?
C14 C1 C6 C7 107.7(6) . . . . ?
C10 C1 C6 C7 -10.9(6) . . . . ?
C3 C4 C5 C6 -54.9(8) . . . . ?
C1 C6 C5 C4 46.5(8) . . . . ?
C7 C6 C5 C4 169.5(6) . . . . ?
Cs1 O4 C13 O3 47.1(8) . . . . ?
Cs1 O4 C13 C12 -131.8(7) . . . . ?
C11 C12 C13 O3 6.9(12) . . . . ?
C7 C12 C13 O3 -170.1(7) . . . . ?
C11 C12 C13 O4 -174.1(8) . . . . ?
C7 C12 C13 O4 8.9(11) . . . . ?
C11 C12 C13 Cs1 89.9(8) . . . . ?
C7 C12 C13 Cs1 -87.1(8) . . . . ?
O4 C13 O3 Cs1 53.4(12) . . . 2_645 ?
C12 C13 O3 Cs1 -127.6(7) . . . 2_645 ?
Cs1 C13 O3 Cs1 104.1(7) . . . 2_645 ?
O4 C13 O3 Cs1 -50.7(9) . . . . ?
C12 C13 O3 Cs1 128.3(6) . . . . ?
C1 C2 C3 C4 5.8(11) . . . . ?
C5 C4 C3 C2 29.3(10) . . . . ?
C11 C12 C7 C8 -58.9(7) . . . . ?
C13 C12 C7 C8 118.4(7) . . . . ?
C11 C12 C7 C6 59.5(7) . . . . ?
C13 C12 C7 C6 -123.2(7) . . . . ?
C9 C8 C7 C12 66.2(7) . . . . ?
C9 C8 C7 C6 -51.8(7) . . . . ?
C5 C6 C7 C12 -173.4(6) . . . . ?
C1 C6 C7 C12 -48.1(7) . . . . ?
C5 C6 C7 C8 -58.6(7) . . . . ?
C1 C6 C7 C8 66.8(6) . . . . ?

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
C15 H15C O5W 0.96 2.50 3.400(13) 155.4 2_645
O5W H5W2 O4 0.830(2) 2.14(5) 2.947(10) 163(15) 3_656
O6W H6W1 O3 0.830(2) 1.965(9) 2.794(8) 177(10) 4_566

_refine_diff_density_max         1.609
_refine_diff_density_min         -1.092
_refine_diff_density_rms         0.129





_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: deuterated chloroform'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound_20
_database_code_depnum_ccdc_archive 'CCDC 1530224'
_audit_update_record             
;
2017-01-30 deposited with the CCDC.
2017-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'rac-(6aR,10aS)-3,3a,4,5,6,6a,7,8-octahydro-3,6-methanobenzo[h] indole-2,11(1H)-dione'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H15 N O2'
_chemical_formula_sum            'C13 H15 N O2'
_chemical_formula_weight         217.26

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                   8.759(2)
_cell_length_b                   10.165(2)
_cell_length_c                   11.997(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.231(14)
_cell_angle_gamma                90
_cell_volume                     1059.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2348
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      29.575

_exptl_crystal_description       cube
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Nonius Kappa CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7833
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0526
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.968
_diffrn_reflns_theta_max         29.565
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2933
_reflns_number_gt                1946
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    'MERCURY (Macrae, 1999)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_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. 
 two reflection were omitted due to beamstop shading.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0505P)²+0.1944P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       .
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2931
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1263
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9)
;

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
O15 O 0.67550(11) 0.51866(11) 0.43192(9) 0.0432(3) Uani 1 1 d . . . . .
O16 O 0.68755(13) 0.53365(13) 0.14409(10) 0.0555(3) Uani 1 1 d . . . . .
N14 N 0.44212(13) 0.61876(12) 0.38009(10) 0.0356(3) Uani 1 1 d . . . . .
H14 H 0.3896 0.5786 0.4283 0.043 Uiso 1 1 d R U . . .
C1 C 0.52041(16) 0.80278(14) 0.28711(12) 0.0339(3) Uani 1 1 d . . . . .
H1 H 0.5471 0.8578 0.3538 0.041 Uiso 1 1 calc R U . . .
C2 C 0.63814(16) 0.69023(15) 0.28573(11) 0.0346(3) Uani 1 1 d . . . . .
H2 H 0.7453 0.7198 0.3000 0.041 Uiso 1 1 calc R U . . .
C3 C 0.60146(16) 0.61486(15) 0.17570(12) 0.0366(3) Uani 1 1 d . . . . .
C4 C 0.45179(16) 0.65810(15) 0.11057(11) 0.0369(3) Uani 1 1 d . . . . .
H4 H 0.4263 0.6031 0.0437 0.044 Uiso 1 1 calc R U . . .
C5 C 0.31849(15) 0.65698(14) 0.18444(11) 0.0336(3) Uani 1 1 d . . . . .
H5 H 0.2933 0.5649 0.1981 0.040 Uiso 1 1 calc R U . . .
C6 C 0.17455(17) 0.72201(17) 0.12336(14) 0.0446(4) Uani 1 1 d . . . . .
H6A H 0.2008 0.8093 0.0993 0.054 Uiso 1 1 calc R U . . .
H6B H 0.1387 0.6712 0.0567 0.054 Uiso 1 1 calc R U . . .
C7 C 0.04574(17) 0.73278(18) 0.19639(15) 0.0524(5) Uani 1 1 d . . . . .
H7A H -0.0365 0.7867 0.1588 0.063 Uiso 1 1 calc R U . . .
H7B H 0.0044 0.6460 0.2079 0.063 Uiso 1 1 calc R U . . .
C8 C 0.10394(19) 0.79237(17) 0.30690(15) 0.0500(4) Uani 1 1 d . . . . .
H8 H 0.0334 0.8332 0.3473 0.060 Uiso 1 1 calc R U . . .
C9 C 0.25002(18) 0.79061(15) 0.35097(13) 0.0417(4) Uani 1 1 d . . . . .
H9 H 0.2770 0.8356 0.4181 0.050 Uiso 1 1 calc R U . . .
C10 C 0.37484(15) 0.72094(14) 0.29996(11) 0.0314(3) Uani 1 1 d . . . . .
C11 C 0.50253(18) 0.88794(15) 0.18187(12) 0.0401(4) Uani 1 1 d . . . . .
H11A H 0.5913 0.9450 0.1824 0.048 Uiso 1 1 calc R U . . .
H11B H 0.4117 0.9428 0.1808 0.048 Uiso 1 1 calc R U . . .
C12 C 0.48758(17) 0.80079(16) 0.07679(12) 0.0417(4) Uani 1 1 d . . . . .
H12A H 0.5827 0.8027 0.0433 0.050 Uiso 1 1 calc R U . . .
H12B H 0.4055 0.8334 0.0219 0.050 Uiso 1 1 calc R U . . .
C13 C 0.59189(16) 0.59799(14) 0.37623(11) 0.0340(3) Uani 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
O15 C13 1.2287(17) . ?
O16 C3 1.2107(18) . ?
N14 C13 1.3353(18) . ?
N14 C10 1.4858(17) . ?
N14 H14 0.8829 . ?
C1 C11 1.523(2) . ?
C1 C2 1.542(2) . ?
C1 C10 1.5463(19) . ?
C1 H1 0.9800 . ?
C2 C3 1.525(2) . ?
C2 C13 1.527(2) . ?
C2 H2 0.9800 . ?
C3 C4 1.505(2) . ?
C4 C12 1.549(2) . ?
C4 C5 1.552(2) . ?
C4 H4 0.9800 . ?
C5 C6 1.527(2) . ?
C5 C10 1.5540(19) . ?
C5 H5 0.9800 . ?
C6 C7 1.517(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.488(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.322(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.4966(19) . ?
C9 H9 0.9300 . ?
C11 C12 1.533(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N14 C10 113.55(11) . . ?
C13 N14 H14 123.0 . . ?
C10 N14 H14 123.4 . . ?
C11 C1 C2 114.34(11) . . ?
C11 C1 C10 112.86(12) . . ?
C2 C1 C10 99.38(11) . . ?
C11 C1 H1 109.9 . . ?
C2 C1 H1 109.9 . . ?
C10 C1 H1 109.9 . . ?
C3 C2 C13 105.13(11) . . ?
C3 C2 C1 108.29(11) . . ?
C13 C2 C1 102.14(11) . . ?
C3 C2 H2 113.5 . . ?
C13 C2 H2 113.5 . . ?
C1 C2 H2 113.5 . . ?
O16 C3 C4 124.94(13) . . ?
O16 C3 C2 122.82(13) . . ?
C4 C3 C2 112.18(12) . . ?
C3 C4 C12 102.57(12) . . ?
C3 C4 C5 111.73(11) . . ?
C12 C4 C5 110.36(12) . . ?
C3 C4 H4 110.6 . . ?
C12 C4 H4 110.6 . . ?
C5 C4 H4 110.6 . . ?
C6 C5 C4 110.97(12) . . ?
C6 C5 C10 113.41(12) . . ?
C4 C5 C10 109.20(11) . . ?
C6 C5 H5 107.7 . . ?
C4 C5 H5 107.7 . . ?
C10 C5 H5 107.7 . . ?
C7 C6 C5 112.54(13) . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C6 110.34(13) . . ?
C8 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 C7 123.83(15) . . ?
C9 C8 H8 118.1 . . ?
C7 C8 H8 118.1 . . ?
C8 C9 C10 124.27(16) . . ?
C8 C9 H9 117.9 . . ?
C10 C9 H9 117.9 . . ?
N14 C10 C9 108.47(11) . . ?
N14 C10 C1 100.12(10) . . ?
C9 C10 C1 116.11(12) . . ?
N14 C10 C5 109.88(11) . . ?
C9 C10 C5 113.35(12) . . ?
C1 C10 C5 108.03(10) . . ?
C1 C11 C12 110.04(12) . . ?
C1 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
C1 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C11 C12 C4 108.98(11) . . ?
C11 C12 H12A 109.9 . . ?
C4 C12 H12A 109.9 . . ?
C11 C12 H12B 109.9 . . ?
C4 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
O15 C13 N14 127.29(14) . . ?
O15 C13 C2 126.59(13) . . ?
N14 C13 C2 106.09(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C1 C2 C3 -50.53(15) . . . . ?
C10 C1 C2 C3 69.92(13) . . . . ?
C11 C1 C2 C13 -161.16(11) . . . . ?
C10 C1 C2 C13 -40.71(12) . . . . ?
C13 C2 C3 O16 -82.49(17) . . . . ?
C1 C2 C3 O16 168.92(14) . . . . ?
C13 C2 C3 C4 100.19(13) . . . . ?
C1 C2 C3 C4 -8.40(15) . . . . ?
O16 C3 C4 C12 -110.29(17) . . . . ?
C2 C3 C4 C12 66.96(14) . . . . ?
O16 C3 C4 C5 131.51(15) . . . . ?
C2 C3 C4 C5 -51.23(16) . . . . ?
C3 C4 C5 C6 170.69(13) . . . . ?
C12 C4 C5 C6 57.26(16) . . . . ?
C3 C4 C5 C10 44.97(16) . . . . ?
C12 C4 C5 C10 -68.47(14) . . . . ?
C4 C5 C6 C7 -175.35(13) . . . . ?
C10 C5 C6 C7 -52.01(18) . . . . ?
C5 C6 C7 C8 50.21(18) . . . . ?
C6 C7 C8 C9 -23.1(2) . . . . ?
C7 C8 C9 C10 -4.3(2) . . . . ?
C13 N14 C10 C9 -147.57(13) . . . . ?
C13 N14 C10 C1 -25.49(14) . . . . ?
C13 N14 C10 C5 88.02(14) . . . . ?
C8 C9 C10 N14 -118.59(16) . . . . ?
C8 C9 C10 C1 129.70(16) . . . . ?
C8 C9 C10 C5 3.7(2) . . . . ?
C11 C1 C10 N14 160.81(11) . . . . ?
C2 C1 C10 N14 39.29(12) . . . . ?
C11 C1 C10 C9 -82.71(15) . . . . ?
C2 C1 C10 C9 155.77(12) . . . . ?
C11 C1 C10 C5 45.89(15) . . . . ?
C2 C1 C10 C5 -75.64(12) . . . . ?
C6 C5 C10 N14 145.88(12) . . . . ?
C4 C5 C10 N14 -89.81(13) . . . . ?
C6 C5 C10 C9 24.34(17) . . . . ?
C4 C5 C10 C9 148.64(12) . . . . ?
C6 C5 C10 C1 -105.81(13) . . . . ?
C4 C5 C10 C1 18.50(15) . . . . ?
C2 C1 C11 C12 46.34(16) . . . . ?
C10 C1 C11 C12 -66.28(15) . . . . ?
C1 C11 C12 C4 15.07(16) . . . . ?
C3 C4 C12 C11 -70.53(14) . . . . ?
C5 C4 C12 C11 48.63(16) . . . . ?
C10 N14 C13 O15 -179.11(13) . . . . ?
C10 N14 C13 C2 -0.74(15) . . . . ?
C3 C2 C13 O15 92.33(16) . . . . ?
C1 C2 C13 O15 -154.67(14) . . . . ?
C3 C2 C13 N14 -86.06(13) . . . . ?
C1 C2 C13 N14 26.94(14) . . . . ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.043






_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hot ethyl acetate'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound_28
_database_code_depnum_ccdc_archive 'CCDC 1530226'
_audit_update_record             
;
2017-01-30 deposited with the CCDC.
2017-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 O5'
_chemical_formula_sum            'C15 H18 O5'
_chemical_formula_weight         278.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 '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                   8.4275(9)
_cell_length_b                   17.5160(13)
_cell_length_c                   8.9932(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.603(7)
_cell_angle_gamma                90
_cell_volume                     1308.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    3054
_cell_measurement_theta_min      5.0
_cell_measurement_theta_max      71.9

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.880
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.917
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.344
_exptl_absorpt_process_details   'REQAB,(Rigaku Higashi, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  'OSMIC CMF mirrors'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'RIGAKU RAPID2 curved IP'
_diffrn_measurement_device       
;
Crystal Chi-partial Goniometer 
;
_diffrn_measurement_device_type  
;
Rigaku Rigaku mm007HF Rapid2
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            6338
_diffrn_reflns_av_unetI/netI     0.1059
_diffrn_reflns_av_R_equivalents  0.1152
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         7.107
_diffrn_reflns_theta_max         52.615
_diffrn_reflns_theta_full        52.615
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1494
_reflns_number_gt                999
_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       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0964P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1491
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0650
_refine_ls_wR_factor_ref         0.1856
_refine_ls_wR_factor_gt          0.1500
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
O1 O 0.4039(3) 0.61743(13) 1.1030(3) 0.0561(9) Uani 1 1 d . . . . .
O2 O 0.4012(3) 0.77400(13) 0.8354(3) 0.0588(8) Uani 1 1 d . . . . .
H2 H 0.4188 0.8125 0.7850 0.088 Uiso 1 1 calc R U . . .
O3 O 0.0532(3) 0.40553(14) 0.8292(3) 0.0607(9) Uani 1 1 d . . . . .
O4 O 0.6128(3) 0.67223(13) 1.0220(3) 0.0548(8) Uani 1 1 d . . . . .
O5 O 0.1931(3) 0.37395(14) 0.6468(3) 0.0673(9) Uani 1 1 d . . . . .
C1 C 0.2169(4) 0.63439(18) 0.7909(4) 0.0451(10) Uani 1 1 d . . . . .
H1 H 0.1649 0.6746 0.8453 0.054 Uiso 1 1 calc R U . . .
C2 C 0.1572(4) 0.5558(2) 0.8216(4) 0.0512(11) Uani 1 1 d . . . . .
H2A H 0.0832 0.5468 0.8886 0.061 Uiso 1 1 calc R U . . .
C3 C 0.2169(4) 0.4998(2) 0.7471(4) 0.0459(10) Uani 1 1 d . . . . .
C4 C 0.3424(4) 0.52510(18) 0.6581(4) 0.0488(10) Uani 1 1 d . . . . .
H4 H 0.3861 0.4806 0.6082 0.059 Uiso 1 1 calc R U . . .
C5 C 0.4776(4) 0.56514(18) 0.7690(4) 0.0448(10) Uani 1 1 d . . . . .
H5 H 0.5101 0.5295 0.8556 0.054 Uiso 1 1 calc R U . . .
C6 C 0.6299(4) 0.5840(2) 0.7035(4) 0.0566(11) Uani 1 1 d . . . . .
H6A H 0.6885 0.5361 0.6906 0.068 Uiso 1 1 calc R U . . .
H6B H 0.5986 0.6075 0.6028 0.068 Uiso 1 1 calc R U . . .
C7 C 0.7417(5) 0.6383(2) 0.8044(5) 0.0632(12) Uani 1 1 d . . . . .
H7A H 0.8087 0.6087 0.8853 0.076 Uiso 1 1 calc R U . . .
H7B H 0.8145 0.6636 0.7439 0.076 Uiso 1 1 calc R U . . .
C8 C 0.6488(5) 0.6985(2) 0.8747(4) 0.0558(11) Uani 1 1 d . . . . .
H8 H 0.7090 0.7479 0.8858 0.067 Uiso 1 1 calc R U . . .
C9 C 0.4811(4) 0.70948(19) 0.7858(4) 0.0497(11) Uani 1 1 d . . . . .
H9 H 0.4816 0.7110 0.6747 0.060 Uiso 1 1 calc R U . . .
C10 C 0.4018(4) 0.63709(17) 0.8324(4) 0.0430(10) Uani 1 1 d . . . . .
C11 C 0.1754(4) 0.64460(19) 0.6175(4) 0.0556(11) Uani 1 1 d . . . . .
H11A H 0.0576 0.6407 0.5848 0.067 Uiso 1 1 calc R U . . .
H11B H 0.2102 0.6958 0.5890 0.067 Uiso 1 1 calc R U . . .
C12 C 0.2606(4) 0.5829(2) 0.5390(4) 0.0571(11) Uani 1 1 d . . . . .
H12A H 0.3424 0.6067 0.4866 0.069 Uiso 1 1 calc R U . . .
H12B H 0.1814 0.5562 0.4629 0.069 Uiso 1 1 calc R U . . .
C13 C 0.1577(5) 0.4204(2) 0.7351(5) 0.0550(11) Uani 1 1 d . . . . .
C14 C -0.0150(5) 0.3299(2) 0.8207(4) 0.0713(13) Uani 1 1 d . . . . .
H14A H -0.0729 0.3207 0.7184 0.107 Uiso 1 1 calc R U . . .
H14B H -0.0898 0.3254 0.8928 0.107 Uiso 1 1 calc R U . . .
H14C H 0.0713 0.2922 0.8450 0.107 Uiso 1 1 calc R U . . .
C15 C 0.4652(5) 0.63979(18) 0.9999(4) 0.0473(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.200(4) . ?
O2 C9 1.425(4) . ?
O2 H2 0.8400 . ?
O3 C13 1.345(4) . ?
O3 C14 1.441(4) . ?
O4 C15 1.352(4) . ?
O4 C8 1.481(4) . ?
O5 C13 1.208(4) . ?
C1 C2 1.508(4) . ?
C1 C10 1.541(5) . ?
C1 C11 1.550(5) . ?
C1 H1 1.0000 . ?
C2 C3 1.332(4) . ?
C2 H2A 0.9500 . ?
C3 C13 1.476(5) . ?
C3 C4 1.496(4) . ?
C4 C12 1.550(4) . ?
C4 C5 1.551(4) . ?
C4 H4 1.0000 . ?
C5 C6 1.535(4) . ?
C5 C10 1.563(4) . ?
C5 H5 1.0000 . ?
C6 C7 1.527(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.512(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.515(5) . ?
C8 H8 1.0000 . ?
C9 C10 1.524(4) . ?
C9 H9 1.0000 . ?
C10 C15 1.513(5) . ?
C11 C12 1.533(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
C9 O2 H2 109.5 . . ?
C13 O3 C14 116.2(3) . . ?
C15 O4 C8 108.6(3) . . ?
C2 C1 C10 109.8(3) . . ?
C2 C1 C11 105.3(3) . . ?
C10 C1 C11 106.8(3) . . ?
C2 C1 H1 111.6 . . ?
C10 C1 H1 111.6 . . ?
C11 C1 H1 111.6 . . ?
C3 C2 C1 114.5(3) . . ?
C3 C2 H2A 122.8 . . ?
C1 C2 H2A 122.8 . . ?
C2 C3 C13 125.3(4) . . ?
C2 C3 C4 114.3(3) . . ?
C13 C3 C4 120.1(4) . . ?
C3 C4 C12 106.9(3) . . ?
C3 C4 C5 107.4(3) . . ?
C12 C4 C5 110.1(3) . . ?
C3 C4 H4 110.8 . . ?
C12 C4 H4 110.8 . . ?
C5 C4 H4 110.8 . . ?
C6 C5 C4 115.0(3) . . ?
C6 C5 C10 112.7(3) . . ?
C4 C5 C10 107.4(3) . . ?
C6 C5 H5 107.1 . . ?
C4 C5 H5 107.1 . . ?
C10 C5 H5 107.1 . . ?
C7 C6 C5 112.2(3) . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C6 111.8(3) . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
O4 C8 C7 110.8(3) . . ?
O4 C8 C9 101.5(3) . . ?
C7 C8 C9 111.7(3) . . ?
O4 C8 H8 110.8 . . ?
C7 C8 H8 110.8 . . ?
C9 C8 H8 110.8 . . ?
O2 C9 C8 112.6(3) . . ?
O2 C9 C10 108.8(3) . . ?
C8 C9 C10 99.4(3) . . ?
O2 C9 H9 111.8 . . ?
C8 C9 H9 111.8 . . ?
C10 C9 H9 111.8 . . ?
C15 C10 C9 98.6(3) . . ?
C15 C10 C1 114.6(3) . . ?
C9 C10 C1 115.5(3) . . ?
C15 C10 C5 106.9(3) . . ?
C9 C10 C5 110.2(3) . . ?
C1 C10 C5 110.2(3) . . ?
C12 C11 C1 109.7(3) . . ?
C12 C11 H11A 109.7 . . ?
C1 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C1 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C11 C12 C4 109.3(3) . . ?
C11 C12 H12A 109.8 . . ?
C4 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
C4 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?
O5 C13 O3 122.9(4) . . ?
O5 C13 C3 124.4(4) . . ?
O3 C13 C3 112.7(4) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 O4 121.8(3) . . ?
O1 C15 C10 129.3(4) . . ?
O4 C15 C10 108.8(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
C10 C1 C2 C3 -58.5(4) . . . . ?
C11 C1 C2 C3 56.1(4) . . . . ?
C1 C2 C3 C13 -168.4(3) . . . . ?
C1 C2 C3 C4 5.1(4) . . . . ?
C2 C3 C4 C12 -61.6(4) . . . . ?
C13 C3 C4 C12 112.3(3) . . . . ?
C2 C3 C4 C5 56.5(4) . . . . ?
C13 C3 C4 C5 -129.7(3) . . . . ?
C3 C4 C5 C6 170.8(3) . . . . ?
C12 C4 C5 C6 -73.2(4) . . . . ?
C3 C4 C5 C10 -63.0(3) . . . . ?
C12 C4 C5 C10 53.0(4) . . . . ?
C4 C5 C6 C7 167.2(3) . . . . ?
C10 C5 C6 C7 43.8(4) . . . . ?
C5 C6 C7 C8 -38.2(4) . . . . ?
C15 O4 C8 C7 -93.9(3) . . . . ?
C15 O4 C8 C9 24.9(3) . . . . ?
C6 C7 C8 O4 90.5(4) . . . . ?
C6 C7 C8 C9 -21.8(4) . . . . ?
O4 C8 C9 O2 71.4(3) . . . . ?
C7 C8 C9 O2 -170.5(3) . . . . ?
O4 C8 C9 C10 -43.5(3) . . . . ?
C7 C8 C9 C10 74.6(3) . . . . ?
O2 C9 C10 C15 -72.7(3) . . . . ?
C8 C9 C10 C15 45.1(3) . . . . ?
O2 C9 C10 C1 49.9(4) . . . . ?
C8 C9 C10 C1 167.7(3) . . . . ?
O2 C9 C10 C5 175.6(2) . . . . ?
C8 C9 C10 C5 -66.6(3) . . . . ?
C2 C1 C10 C15 -74.9(4) . . . . ?
C11 C1 C10 C15 171.4(3) . . . . ?
C2 C1 C10 C9 171.4(3) . . . . ?
C11 C1 C10 C9 57.7(4) . . . . ?
C2 C1 C10 C5 45.7(4) . . . . ?
C11 C1 C10 C5 -68.0(3) . . . . ?
C6 C5 C10 C15 -95.5(3) . . . . ?
C4 C5 C10 C15 136.9(3) . . . . ?
C6 C5 C10 C9 10.7(4) . . . . ?
C4 C5 C10 C9 -116.9(3) . . . . ?
C6 C5 C10 C1 139.4(3) . . . . ?
C4 C5 C10 C1 11.8(4) . . . . ?
C2 C1 C11 C12 -60.1(4) . . . . ?
C10 C1 C11 C12 56.6(3) . . . . ?
C1 C11 C12 C4 6.9(4) . . . . ?
C3 C4 C12 C11 51.6(4) . . . . ?
C5 C4 C12 C11 -64.7(4) . . . . ?
C14 O3 C13 O5 0.5(5) . . . . ?
C14 O3 C13 C3 177.8(3) . . . . ?
C2 C3 C13 O5 166.4(4) . . . . ?
C4 C3 C13 O5 -6.7(5) . . . . ?
C2 C3 C13 O3 -10.9(5) . . . . ?
C4 C3 C13 O3 176.0(3) . . . . ?
C8 O4 C15 O1 -176.0(3) . . . . ?
C8 O4 C15 C10 4.8(3) . . . . ?
C9 C10 C15 O1 148.8(4) . . . . ?
C1 C10 C15 O1 25.5(5) . . . . ?
C5 C10 C15 O1 -96.9(4) . . . . ?
C9 C10 C15 O4 -32.1(3) . . . . ?
C1 C10 C15 O4 -155.4(3) . . . . ?
C5 C10 C15 O4 82.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.84 2.03 2.828(3) 158.0 4_575
C7 H7A O3 0.99 2.65 3.540(5) 150.1 3_667
C8 H8 O5 1.00 2.39 3.368(5) 165.1 2_656

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.061




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hot ethyl acetate'
