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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 N2 O8'
_chemical_formula_weight         344.32
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   7.7195(5)
_cell_length_b                   8.2128(5)
_cell_length_c                   26.4533(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1677.11(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    17720
_cell_measurement_theta_min      0.996
_cell_measurement_theta_max      24.11

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_T_max  0.989

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω and π scans'
_diffrn_detector_area_resol_mean 16.5467
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31431
_diffrn_reflns_av_R_equivalents  0.0771
_diffrn_reflns_av_sigmaI/netI    0.0714
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         33.15
_reflns_number_total             5974
_reflns_number_gt                4010
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.6 (release 27-01-2011 CrysAlis171 .NET)
(compiled Jan 27 2011,13:34:29)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.6 (release 27-01-2011 CrysAlis171 .NET)
(compiled Jan 27 2011,13:34:29)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.6 (release 27-01-2011 CrysAlis171 .NET)
(compiled Jan 27 2011,13:34:29)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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.
During the refinement, the restraint command 'DFIX' was also used to refine
the distances of O-H bonds and H-O-H angles in the two hydration water 
molecules of this compound. These atoms are as follows: O7 H7A H7B O8 H8A H8B. 
;

_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)+(0.0388P)²+0.1352P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_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'
_refine_ls_abs_structure_Flack   -0.3(11)
_refine_ls_number_reflns         5974
_refine_ls_number_parameters     245
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1123
_refine_ls_R_factor_gt           0.0678
_refine_ls_wR_factor_ref         0.1210
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
C1 C 0.1907(3) 0.9936(3) 0.23557(7) 0.0338(5) Uani 1 1 d . . .
C2 C 0.2609(3) 0.8262(2) 0.24782(8) 0.0321(5) Uani 1 1 d . . .
H2 H 0.1706 0.7471 0.2392 0.039 Uiso 1 1 calc R . .
C3 C 0.2996(4) 0.8071(3) 0.30363(8) 0.0507(6) Uani 1 1 d . . .
H3A H 0.3302 0.6961 0.3106 0.076 Uiso 1 1 calc R . .
H3B H 0.1989 0.8361 0.3229 0.076 Uiso 1 1 calc R . .
H3C H 0.3942 0.8771 0.3128 0.076 Uiso 1 1 calc R . .
C4 C 0.4054(3) 0.7757(2) 0.16824(8) 0.0293(4) Uani 1 1 d . . .
C5 C 0.5616(3) 0.7124(2) 0.14152(7) 0.0284(4) Uani 1 1 d . . .
C6 C 0.7305(3) 0.7426(2) 0.15733(7) 0.0316(4) Uani 1 1 d . . .
H6 H 0.7505 0.8104 0.1849 0.038 Uiso 1 1 calc R . .
C7 C 0.8691(3) 0.6720(2) 0.13224(8) 0.0321(5) Uani 1 1 d . . .
H7 H 0.9816 0.6904 0.1434 0.039 Uiso 1 1 calc R . .
C8 C 0.8397(3) 0.5738(2) 0.09031(7) 0.0281(4) Uani 1 1 d . . .
C9 C 0.6719(3) 0.5469(2) 0.07415(7) 0.0308(5) Uani 1 1 d . . .
H9 H 0.6522 0.4819 0.0459 0.037 Uiso 1 1 calc R . .
C10 C 0.5332(3) 0.6151(2) 0.09935(7) 0.0313(4) Uani 1 1 d . . .
H10 H 0.4209 0.5960 0.0881 0.038 Uiso 1 1 calc R . .
C11 C 0.9902(3) 0.4942(2) 0.06439(7) 0.0307(4) Uani 1 1 d . . .
C12 C 1.1072(3) 0.3997(2) -0.01634(8) 0.0328(4) Uani 1 1 d . . .
H12 H 1.1383 0.2968 0.0000 0.039 Uiso 1 1 calc R . .
C13 C 1.0346(3) 0.3617(3) -0.06850(8) 0.0480(6) Uani 1 1 d . . .
H13A H 0.9360 0.2913 -0.0652 0.072 Uiso 1 1 calc R . .
H13B H 1.1219 0.3087 -0.0884 0.072 Uiso 1 1 calc R . .
H13C H 1.0002 0.4611 -0.0848 0.072 Uiso 1 1 calc R . .
C14 C 1.2695(3) 0.5030(2) -0.02076(7) 0.0335(5) Uani 1 1 d . . .
H1A H 0.495(3) 0.748(3) 0.2318(8) 0.041(8) Uiso 1 1 d . . .
H2A H 0.900(3) 0.526(3) -0.0005(9) 0.034(6) Uiso 1 1 d . . .
H7A H 0.122(4) 0.425(4) 0.2083(10) 0.096(12) Uiso 1 1 d D . .
H8A H 0.685(5) 0.697(3) 0.9647(9) 0.094(12) Uiso 1 1 d D . .
H7B H 0.172(4) 0.401(4) 0.1570(7) 0.097(12) Uiso 1 1 d D . .
H8B H 0.699(3) 0.625(3) 0.9171(6) 0.056(8) Uiso 1 1 d D . .
N1 N 0.4134(3) 0.7843(2) 0.21869(7) 0.0331(4) Uani 1 1 d . . .
N2 N 0.9776(3) 0.4796(2) 0.01429(7) 0.0351(4) Uani 1 1 d . . .
O1 O 0.0406(2) 1.0275(2) 0.24299(7) 0.0524(5) Uani 1 1 d . . .
O2 O 0.3054(2) 1.09929(17) 0.21837(6) 0.0405(4) Uani 1 1 d . . .
H2B H 0.2562 1.1843 0.2107 0.061 Uiso 1 1 calc R . .
O3 O 0.27216(19) 0.81523(18) 0.14601(5) 0.0390(4) Uani 1 1 d . . .
O4 O 1.1188(2) 0.44584(19) 0.08760(6) 0.0420(4) Uani 1 1 d . . .
O5 O 1.2809(2) 0.64219(18) -0.00751(6) 0.0472(4) Uani 1 1 d . . .
O6 O 1.3966(2) 0.4230(2) -0.04214(8) 0.0567(5) Uani 1 1 d . . .
H6A H 1.4810 0.4830 -0.0449 0.085 Uiso 1 1 calc R . .
O7 O 0.1975(2) 0.3810(2) 0.18956(7) 0.0525(5) Uani 1 1 d D . .
O8 O 0.6734(2) 0.6034(2) 0.94902(6) 0.0417(4) Uani 1 1 d 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 O1 1.207(3) . ?
C1 O2 1.321(3) . ?
C1 C2 1.513(3) . ?
C2 N1 1.449(3) . ?
C2 C3 1.514(3) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 O3 1.229(2) . ?
C4 N1 1.338(3) . ?
C4 C5 1.491(3) . ?
C5 C10 1.390(3) . ?
C5 C6 1.392(3) . ?
C6 C7 1.386(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.390(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.382(3) . ?
C8 C11 1.499(3) . ?
C9 C10 1.380(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 O4 1.233(2) . ?
C11 N2 1.334(3) . ?
C12 N2 1.445(3) . ?
C12 C14 1.517(3) . ?
C12 C13 1.522(3) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O5 1.199(2) . ?
C14 O6 1.310(2) . ?
N1 H1A 0.78(3) . ?
N2 H2A 0.81(2) . ?
O2 H2B 0.8200 . ?
O6 H6A 0.8200 . ?
O7 H7A 0.845(17) . ?
O7 H7B 0.897(17) . ?
O8 H8A 0.876(17) . ?
O8 H8B 0.884(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
O1 C1 O2 123.2(2) . . ?
O1 C1 C2 121.2(2) . . ?
O2 C1 C2 115.49(19) . . ?
N1 C2 C1 113.16(18) . . ?
N1 C2 C3 109.50(19) . . ?
C1 C2 C3 111.93(17) . . ?
N1 C2 H2 107.3 . . ?
C1 C2 H2 107.3 . . ?
C3 C2 H2 107.3 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O3 C4 N1 120.15(19) . . ?
O3 C4 C5 122.82(18) . . ?
N1 C4 C5 117.01(18) . . ?
C10 C5 C6 119.43(18) . . ?
C10 C5 C4 116.97(18) . . ?
C6 C5 C4 123.57(18) . . ?
C7 C6 C5 120.33(18) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 119.90(19) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 119.52(18) . . ?
C9 C8 C11 121.00(17) . . ?
C7 C8 C11 119.44(18) . . ?
C10 C9 C8 120.85(18) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C5 119.93(19) . . ?
C9 C10 H10 120.0 . . ?
C5 C10 H10 120.0 . . ?
O4 C11 N2 121.63(19) . . ?
O4 C11 C8 122.45(18) . . ?
N2 C11 C8 115.92(18) . . ?
N2 C12 C14 111.16(16) . . ?
N2 C12 C13 110.31(18) . . ?
C14 C12 C13 110.41(17) . . ?
N2 C12 H12 108.3 . . ?
C14 C12 H12 108.3 . . ?
C13 C12 H12 108.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 O6 123.3(2) . . ?
O5 C14 C12 124.85(18) . . ?
O6 C14 C12 111.83(17) . . ?
C4 N1 C2 120.37(19) . . ?
C4 N1 H1A 117.5(18) . . ?
C2 N1 H1A 120.7(18) . . ?
C11 N2 C12 123.20(19) . . ?
C11 N2 H2A 119.5(17) . . ?
C12 N2 H2A 116.9(17) . . ?
C1 O2 H2B 109.5 . . ?
C14 O6 H6A 109.5 . . ?
H7A O7 H7B 110(2) . . ?
H8A O8 H8B 105(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O2 0.78(3) 2.37(3) 3.129(3) 167(2) 3_645
N2 H2A O8 0.81(2) 2.29(2) 3.087(3) 168(2) 1_554
O7 H7A O1 0.845(17) 1.987(17) 2.830(3) 175(3) 3_545
O8 H8A O5 0.876(17) 1.89(2) 2.730(2) 159(3) 4_466
O7 H7B O4 0.897(17) 1.918(17) 2.815(2) 180(3) 1_455
O8 H8B O3 0.884(16) 1.831(17) 2.711(2) 173(3) 4_566
O2 H2B O7 0.82 1.77 2.574(2) 166.9 1_565
O6 H6A O8 0.82 1.79 2.610(2) 176.6 1_654

_diffrn_measured_fraction_theta_max 0.951
_diffrn_reflns_theta_full        33.15
_diffrn_measured_fraction_theta_full 0.951
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.046
_database_code_depnum_ccdc_archive 'CCDC 993036'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound2

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H30 N2 O7'
_chemical_formula_weight         410.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   6.9544(5)
_cell_length_b                   11.7552(8)
_cell_length_c                   26.8723(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2196.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19064
_diffrn_reflns_av_unetI/netI     0.0859
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.516
_diffrn_reflns_theta_max         30.590
_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 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6670
_reflns_number_gt                4014
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_fraction_full    0.999

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 TITL P212121 in P2(1)2(1)2(1)
CELL 0.71073 6.9544 11.7552 26.8723 90.000 90.000 90.000
ZERR 4.0000 0.0005 0.0008 0.0019 0.000 0.000 0.000
LATT -1
SYMM 0.5-X, -Y, 0.5+Z
SYMM 0.5+X, 0.5-Y, -Z
SYMM -X, 0.5+Y, 0.5-Z
SFAC C H N O
UNIT 80 120 8 28
MERG 2
FMAP 2
GRID
PLAN 20
TEMP -100
SIZE 0.08 0.07 0.22
DFIX 0.86 0.02 OW1 H1W1
DFIX 0.86 0.02 OW1 H2W1
DANG 1.36 0.04 H1W1 H2W1
DFIX 0.87 0.02 N1 H1A
DFIX 0.87 0.02 N2 H2A
DFIX 0.82 0.02 O3 H3A
DFIX 0.82 0.02 O6 H6A
L.S. 20
ACTA
WGHT    0.073600    0.212500
FVAR       0.18750
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0736P)²+0.2125P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1262 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.1(9)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         6670
_refine_ls_number_parameters     284
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1196
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1635
_refine_ls_wR_factor_gt          0.1383
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.015
_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
O2 O -0.1863(4) 0.8614(2) 0.49414(10) 0.0387(6) Uani 1 1 d . . . . .
O6 O 0.9951(4) 0.6179(2) 0.80611(8) 0.0403(7) Uani 1 1 d D . . . .
N1 N 0.0962(4) 1.0023(2) 0.52783(9) 0.0275(6) Uani 1 1 d D . . . .
O4 O 0.8382(4) 0.6795(2) 0.63112(9) 0.0443(7) Uani 1 1 d . . . . .
C6 C 0.3222(5) 0.8417(3) 0.58518(11) 0.0256(7) Uani 1 1 d . . . . .
H6 H 0.2298 0.8056 0.5645 0.031 Uiso 1 1 calc R U . . .
N2 N 0.8223(4) 0.7784(3) 0.70256(9) 0.0297(6) Uani 1 1 d D . . . .
O1 O 0.0582(4) 1.0989(2) 0.59928(8) 0.0443(8) Uani 1 1 d . . . . .
C8 C -0.0691(5) 1.0513(3) 0.50221(12) 0.0274(7) Uani 1 1 d . . . . .
H8 H -0.1180 1.1190 0.5209 0.033 Uiso 1 1 calc R U . . .
C7 C 0.1426(5) 1.0247(3) 0.57501(11) 0.0263(7) Uani 1 1 d . . . . .
O3 O -0.3988(4) 1.0026(2) 0.49778(11) 0.0422(7) Uani 1 1 d D . . . .
O5 O 0.7723(4) 0.7544(3) 0.79975(9) 0.0475(8) Uani 1 1 d . . . . .
C16 C 0.8978(5) 0.6966(3) 0.78181(11) 0.0295(8) Uani 1 1 d . . . . .
C1 C 0.3038(5) 0.9569(3) 0.59627(11) 0.0253(7) Uani 1 1 d . . . . .
C14 C 0.7659(5) 0.7583(3) 0.65583(11) 0.0299(8) Uani 1 1 d . . . . .
C15 C 0.9605(5) 0.7056(3) 0.72786(12) 0.0293(7) Uani 1 1 d . . . . .
H15 H 0.9538 0.6281 0.7126 0.035 Uiso 1 1 calc R U . . .
C4 C 0.6081(5) 0.8307(3) 0.63547(10) 0.0265(7) Uani 1 1 d . . . . .
C9 C -0.2232(5) 0.9623(3) 0.49840(11) 0.0260(7) Uani 1 1 d . . . . .
C2 C 0.4377(6) 1.0084(3) 0.62787(12) 0.0322(8) Uani 1 1 d . . . . .
H2 H 0.4250 1.0866 0.6361 0.039 Uiso 1 1 calc R U . . .
C3 C 0.5885(6) 0.9457(3) 0.64714(12) 0.0319(8) Uani 1 1 d . . . . .
H3 H 0.6794 0.9812 0.6685 0.038 Uiso 1 1 calc R U . . .
C5 C 0.4746(5) 0.7798(3) 0.60419(11) 0.0265(7) Uani 1 1 d . . . . .
H5 H 0.4880 0.7017 0.5958 0.032 Uiso 1 1 calc R U . . .
C10 C -0.0104(6) 1.0867(4) 0.44785(14) 0.0419(10) Uani 1 1 d . . . . .
H10 H 0.0354 1.0162 0.4306 0.050 Uiso 1 1 calc R U . . .
C17 C 1.1677(6) 0.7516(4) 0.72119(14) 0.0432(10) Uani 1 1 d . . . . .
H17 H 1.1835 0.7689 0.6850 0.052 Uiso 1 1 calc R U . . .
C19 C 1.3248(7) 0.6648(5) 0.7346(2) 0.078(2) Uani 1 1 d . . . . .
H19A H 1.4521 0.7006 0.7294 0.093 Uiso 1 1 calc R U . . .
H19B H 1.3137 0.6461 0.7704 0.093 Uiso 1 1 calc R U . . .
C11 C -0.1840(8) 1.1304(6) 0.41873(19) 0.0783(18) Uani 1 1 d . . . . .
H11A H -0.1465 1.1448 0.3841 0.117 Uiso 1 1 calc R U . . .
H11B H -0.2303 1.2012 0.4338 0.117 Uiso 1 1 calc R U . . .
H11C H -0.2866 1.0733 0.4195 0.117 Uiso 1 1 calc R U . . .
C18 C 1.1944(8) 0.8635(5) 0.74879(18) 0.0657(15) Uani 1 1 d . . . . .
H18A H 1.3171 0.8979 0.7391 0.099 Uiso 1 1 calc R U . . .
H18B H 1.1941 0.8493 0.7847 0.099 Uiso 1 1 calc R U . . .
H18C H 1.0890 0.9153 0.7403 0.099 Uiso 1 1 calc R U . . .
C12 C 0.1554(8) 1.1701(4) 0.44779(18) 0.0609(14) Uani 1 1 d . . . . .
H12A H 0.2526 1.1457 0.4725 0.073 Uiso 1 1 calc R U . . .
H12B H 0.1080 1.2462 0.4577 0.073 Uiso 1 1 calc R U . . .
C20 C 1.3169(10) 0.5557(6) 0.7050(3) 0.110(3) Uani 1 1 d . . . . .
H20A H 1.3013 0.5736 0.6696 0.166 Uiso 1 1 calc R U . . .
H20B H 1.2077 0.5098 0.7163 0.166 Uiso 1 1 calc R U . . .
H20C H 1.4364 0.5130 0.7099 0.166 Uiso 1 1 calc R U . . .
OW1 O 0.3461(4) 0.8543(2) 0.46734(8) 0.0307(6) Uani 1 1 d D . . . .
C13 C 0.2506(9) 1.1779(6) 0.39565(19) 0.0816(18) Uani 1 1 d . . . . .
H13A H 0.1522 1.1951 0.3707 0.122 Uiso 1 1 calc R U . . .
H13B H 0.3120 1.1052 0.3876 0.122 Uiso 1 1 calc R U . . .
H13C H 0.3475 1.2384 0.3958 0.122 Uiso 1 1 calc R U . . .
H2W1 H 0.354(11) 0.785(3) 0.478(2) 0.122 Uiso 1 1 d D U . . .
H1W1 H 0.362(10) 0.845(5) 0.4365(10) 0.122 Uiso 1 1 d D U . . .
H6A H 0.956(9) 0.613(6) 0.8349(13) 0.122 Uiso 1 1 d D U . . .
H3A H -0.464(9) 0.946(4) 0.492(3) 0.122 Uiso 1 1 d D U . . .
H2A H 0.748(7) 0.820(4) 0.7192(19) 0.098 Uiso 1 1 d D U . . .
H1A H 0.160(8) 0.954(4) 0.5096(19) 0.098 Uiso 1 1 d D 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
O2 C9 1.219(4) . ?
O6 C16 1.318(4) . ?
N1 C7 1.334(4) . ?
N1 C8 1.459(4) . ?
O4 C14 1.245(4) . ?
C6 C5 1.384(5) . ?
C6 C1 1.392(5) . ?
N2 C14 1.337(4) . ?
N2 C15 1.455(4) . ?
O1 C7 1.237(4) . ?
C8 C9 1.501(5) . ?
C8 C10 1.573(5) . ?
C7 C1 1.489(5) . ?
O3 C9 1.310(4) . ?
O5 C16 1.208(4) . ?
C16 C15 1.518(5) . ?
C1 C2 1.398(5) . ?
C14 C4 1.493(5) . ?
C15 C17 1.550(5) . ?
C4 C5 1.388(5) . ?
C4 C3 1.395(5) . ?
C2 C3 1.382(5) . ?
C10 C12 1.514(6) . ?
C10 C11 1.528(6) . ?
C17 C18 1.521(7) . ?
C17 C19 1.538(6) . ?
C19 C20 1.509(9) . ?
C12 C13 1.552(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 C8 124.2(3) . . ?
C5 C6 C1 120.2(3) . . ?
C14 N2 C15 121.9(3) . . ?
N1 C8 C9 108.6(3) . . ?
N1 C8 C10 109.8(3) . . ?
C9 C8 C10 107.8(3) . . ?
O1 C7 N1 121.7(3) . . ?
O1 C7 C1 122.2(3) . . ?
N1 C7 C1 116.2(3) . . ?
O5 C16 O6 124.6(3) . . ?
O5 C16 C15 123.3(3) . . ?
O6 C16 C15 112.0(3) . . ?
C6 C1 C2 119.3(3) . . ?
C6 C1 C7 120.5(3) . . ?
C2 C1 C7 120.2(3) . . ?
O4 C14 N2 120.9(3) . . ?
O4 C14 C4 121.7(3) . . ?
N2 C14 C4 117.3(3) . . ?
N2 C15 C16 107.3(3) . . ?
N2 C15 C17 110.8(3) . . ?
C16 C15 C17 113.7(3) . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 C14 117.9(3) . . ?
C3 C4 C14 122.9(3) . . ?
O2 C9 O3 123.2(3) . . ?
O2 C9 C8 122.3(3) . . ?
O3 C9 C8 114.5(3) . . ?
C3 C2 C1 120.2(3) . . ?
C2 C3 C4 120.4(3) . . ?
C6 C5 C4 120.6(3) . . ?
C12 C10 C11 112.5(4) . . ?
C12 C10 C8 111.7(3) . . ?
C11 C10 C8 111.1(3) . . ?
C18 C17 C19 111.9(4) . . ?
C18 C17 C15 111.0(4) . . ?
C19 C17 C15 113.7(3) . . ?
C20 C19 C17 114.5(5) . . ?
C10 C12 C13 111.3(4) . . ?

_refine_diff_density_max         0.592
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.055

_shelxl_version_number           2012-9

_database_code_depnum_ccdc_archive 'CCDC 993037'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound3

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H32 N2 O8'
_chemical_formula_weight         428.47

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   12.374(3)
_cell_length_b                   7.6754(15)
_cell_length_c                   12.714(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.15(3)
_cell_angle_gamma                90
_cell_volume                     1153.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            ?
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.676
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4723
_reflns_number_gt                3783
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 TITL p21 in P2(1)
CELL 0.71073 12.3741 7.6754 12.7144 90.000 107.147 90.000
ZERR 2.0000 0.0025 0.0015 0.0025 0.000 0.030 0.000
LATT -1
SYMM -X, 0.5+Y, -Z
SFAC C H N O
UNIT 40 64 4 16
MERG 2
FMAP 2
GRID
PLAN 50
TEMP -100
SIZE 0.04 0.14 0.21
DFIX 0.86 0.02 OW1 H1W1
DFIX 0.86 0.02 OW1 H2W1
DANG 1.36 0.04 H1W1 H2W1
DFIX 0.86 0.02 OW2 H1W2
DFIX 0.86 0.02 OW2 H2W2
DANG 1.36 0.04 H1W2 H2W2
DFIX 0.82 0.02 O3 H3O
DFIX 0.82 0.02 O6 H6O
DFIX 0.87 0.02 N1 H1N
DFIX 0.87 0.02 N2 H2N
L.S. 20
ACTA
WGHT    0.072400    0.228900
FVAR       2.05363
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0724P)²+0.2289P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1495 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.7(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4723
_refine_ls_number_parameters     299
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1456
_refine_ls_wR_factor_gt          0.1206
_refine_ls_goodness_of_fit_ref   1.217
_refine_ls_restrained_S_all      1.216
_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
OW1 O 0.3695(2) 0.3632(4) 0.5509(2) 0.0309(6) Uani 1 1 d D . . . .
O5 O 0.4213(2) 0.3210(4) 0.9706(2) 0.0363(7) Uani 1 1 d . . . . .
O6 O 0.2576(3) 0.2129(4) 0.9778(3) 0.0445(8) Uani 1 1 d D . . . .
O2 O 0.5714(2) 1.4701(4) 0.5282(2) 0.0337(7) Uani 1 1 d . . . . .
O3 O 0.7382(2) 1.5749(4) 0.5261(3) 0.0393(8) Uani 1 1 d D . . . .
O4 O 0.3337(2) 0.4771(4) 0.7435(2) 0.0322(7) Uani 1 1 d . . . . .
O1 O 0.6485(3) 1.3036(4) 0.7719(2) 0.0384(7) Uani 1 1 d . . . . .
N2 N 0.3235(3) 0.6368(4) 0.8903(3) 0.0287(7) Uani 1 1 d D . . . .
N1 N 0.6654(3) 1.1616(4) 0.6238(2) 0.0262(7) Uani 1 1 d D . . . .
C3 C 0.3967(3) 0.9328(5) 0.7877(3) 0.0270(9) Uani 1 1 d . . . . .
H3 H 0.3330 0.9598 0.8120 0.032 Uiso 1 1 calc R U . . .
C15 C 0.2597(3) 0.5127(5) 0.9347(3) 0.0294(9) Uani 1 1 d . . . . .
H15 H 0.2584 0.5615 1.0073 0.035 Uiso 1 1 calc R U . . .
C1 C 0.5556(3) 1.0270(5) 0.7305(3) 0.0252(8) Uani 1 1 d . . . . .
C4 C 0.4224(3) 0.7584(5) 0.7721(3) 0.0248(8) Uani 1 1 d . . . . .
C6 C 0.5807(3) 0.8542(5) 0.7132(3) 0.0268(8) Uani 1 1 d . . . . .
H6 H 0.6435 0.8280 0.6873 0.032 Uiso 1 1 calc R U . . .
C2 C 0.4637(3) 1.0652(5) 0.7678(3) 0.0270(9) Uani 1 1 d . . . . .
H2 H 0.4468 1.1829 0.7798 0.032 Uiso 1 1 calc R U . . .
C16 C 0.3219(3) 0.3394(6) 0.9608(3) 0.0291(9) Uani 1 1 d . . . . .
C7 C 0.6268(3) 1.1743(5) 0.7108(3) 0.0252(8) Uani 1 1 d . . . . .
C9 C 0.6721(3) 1.4542(5) 0.5472(3) 0.0255(8) Uani 1 1 d . . . . .
C5 C 0.5143(3) 0.7207(5) 0.7335(3) 0.0269(9) Uani 1 1 d . . . . .
H5 H 0.5314 0.6032 0.7211 0.032 Uiso 1 1 calc R U . . .
C14 C 0.3557(3) 0.6123(5) 0.7993(3) 0.0266(9) Uani 1 1 d . . . . .
C11 C 0.8826(4) 1.0630(6) 0.5855(4) 0.0384(10) Uani 1 1 d . . . . .
H11 H 0.8334 0.9759 0.6078 0.046 Uiso 1 1 calc R U . . .
C18 C 0.0706(4) 0.6695(7) 0.8529(4) 0.0473(12) Uani 1 1 d . . . . .
H18 H 0.1074 0.7538 0.8142 0.057 Uiso 1 1 calc R U . . .
C8 C 0.7389(3) 1.2941(5) 0.6001(3) 0.0262(8) Uani 1 1 d . . . . .
H8 H 0.7931 1.3312 0.6717 0.031 Uiso 1 1 calc R U . . .
OW2 O 0.6250(2) 1.4296(4) 0.9578(2) 0.0321(7) Uani 1 1 d D . . . .
C19 C -0.0500(4) 0.6373(8) 0.7798(5) 0.0632(15) Uani 1 1 d . . . . .
H19A H -0.0926 0.7467 0.7697 0.095 Uiso 1 1 calc R U . . .
H19B H -0.0867 0.5512 0.8149 0.095 Uiso 1 1 calc R U . . .
H19C H -0.0479 0.5933 0.7081 0.095 Uiso 1 1 calc R U . . .
C17 C 0.1364(3) 0.4971(6) 0.8665(3) 0.0360(10) Uani 1 1 d . . . . .
H17A H 0.0987 0.4109 0.9018 0.043 Uiso 1 1 calc R U . . .
H17B H 0.1331 0.4520 0.7927 0.043 Uiso 1 1 calc R U . . .
C10 C 0.8079(3) 1.2161(5) 0.5298(3) 0.0315(9) Uani 1 1 d . . . . .
H10A H 0.8564 1.3081 0.5132 0.038 Uiso 1 1 calc R U . . .
H10B H 0.7555 1.1758 0.4591 0.038 Uiso 1 1 calc R U . . .
C13 C 0.9341(5) 0.9748(8) 0.5036(5) 0.0632(15) Uani 1 1 d . . . . .
H13A H 0.9812 0.8765 0.5395 0.095 Uiso 1 1 calc R U . . .
H13B H 0.9806 1.0590 0.4784 0.095 Uiso 1 1 calc R U . . .
H13C H 0.8733 0.9323 0.4404 0.095 Uiso 1 1 calc R U . . .
C12 C 0.9734(4) 1.1201(7) 0.6885(5) 0.0608(15) Uani 1 1 d . . . . .
H12A H 1.0172 1.2157 0.6702 0.091 Uiso 1 1 calc R U . . .
H12B H 1.0237 1.0218 0.7180 0.091 Uiso 1 1 calc R U . . .
H12C H 0.9378 1.1598 0.7436 0.091 Uiso 1 1 calc R U . . .
C20 C 0.0698(5) 0.7493(8) 0.9603(5) 0.0733(18) Uani 1 1 d . . . . .
H20A H 0.0388 0.6656 1.0019 0.110 Uiso 1 1 calc R U . . .
H20B H 0.0229 0.8545 0.9462 0.110 Uiso 1 1 calc R U . . .
H20C H 0.1472 0.7799 1.0028 0.110 Uiso 1 1 calc R U . . .
H2W2 H 0.634(5) 1.381(11) 0.900(4) 0.110 Uiso 1 1 d D U . . .
H2W1 H 0.364(5) 0.388(11) 0.614(3) 0.110 Uiso 1 1 d D U . . .
H1W1 H 0.441(3) 0.372(12) 0.554(6) 0.110 Uiso 1 1 d D U . . .
H1W2 H 0.557(3) 1.425(11) 0.958(5) 0.110 Uiso 1 1 d D U . . .
H3O H 0.697(5) 1.662(7) 0.505(6) 0.110 Uiso 1 1 d D U . . .
H6O H 0.287(6) 0.119(6) 1.004(6) 0.110 Uiso 1 1 d D U . . .
H1N H 0.642(5) 1.074(6) 0.580(5) 0.088 Uiso 1 1 d D U . . .
H2N H 0.344(5) 0.729(6) 0.932(5) 0.088 Uiso 1 1 d D 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
O5 C16 1.207(5) . ?
O6 C16 1.313(5) . ?
O2 C9 1.204(4) . ?
O3 C9 1.315(5) . ?
O4 C14 1.241(5) . ?
O1 C7 1.240(5) . ?
N2 C14 1.343(5) . ?
N2 C15 1.454(5) . ?
N1 C7 1.331(5) . ?
N1 C8 1.454(5) . ?
C3 C2 1.382(6) . ?
C3 C4 1.403(6) . ?
C15 C17 1.521(6) . ?
C15 C16 1.524(6) . ?
C1 C2 1.386(6) . ?
C1 C6 1.395(6) . ?
C1 C7 1.499(5) . ?
C4 C5 1.396(5) . ?
C4 C14 1.493(5) . ?
C6 C5 1.384(6) . ?
C9 C8 1.522(6) . ?
C11 C12 1.516(7) . ?
C11 C13 1.529(7) . ?
C11 C10 1.534(6) . ?
C18 C20 1.499(8) . ?
C18 C19 1.527(7) . ?
C18 C17 1.536(6) . ?
C8 C10 1.528(5) . ?

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
C14 N2 C15 125.2(3) . . ?
C7 N1 C8 121.4(3) . . ?
C2 C3 C4 120.1(3) . . ?
N2 C15 C17 113.5(3) . . ?
N2 C15 C16 111.0(3) . . ?
C17 C15 C16 114.4(3) . . ?
C2 C1 C6 119.9(4) . . ?
C2 C1 C7 118.7(3) . . ?
C6 C1 C7 121.4(3) . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 C14 119.3(3) . . ?
C3 C4 C14 121.3(3) . . ?
C5 C6 C1 120.1(3) . . ?
C3 C2 C1 120.3(4) . . ?
O5 C16 O6 123.0(4) . . ?
O5 C16 C15 124.0(4) . . ?
O6 C16 C15 112.9(3) . . ?
O1 C7 N1 121.0(3) . . ?
O1 C7 C1 121.8(3) . . ?
N1 C7 C1 117.2(3) . . ?
O2 C9 O3 123.9(4) . . ?
O2 C9 C8 124.4(3) . . ?
O3 C9 C8 111.7(3) . . ?
C6 C5 C4 120.2(4) . . ?
O4 C14 N2 122.6(4) . . ?
O4 C14 C4 122.6(3) . . ?
N2 C14 C4 114.8(3) . . ?
C12 C11 C13 111.4(4) . . ?
C12 C11 C10 111.7(4) . . ?
C13 C11 C10 109.9(4) . . ?
C20 C18 C19 110.6(4) . . ?
C20 C18 C17 113.2(4) . . ?
C19 C18 C17 108.6(4) . . ?
N1 C8 C9 111.4(3) . . ?
N1 C8 C10 109.8(3) . . ?
C9 C8 C10 112.5(3) . . ?
C15 C17 C18 113.9(4) . . ?
C8 C10 C11 113.3(3) . . ?

_refine_diff_density_max         0.361
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.131

_shelxl_version_number           2012-9

_database_code_depnum_ccdc_archive 'CCDC 993038'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound4

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H28 N2 O8'
_chemical_formula_weight         400.42

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.5665(10)
_cell_length_b                   7.6596(7)
_cell_length_c                   12.8714(11)
_cell_angle_alpha                90
_cell_angle_beta                 106.949(2)
_cell_angle_gamma                90
_cell_volume                     996.50(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9773
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.654
_diffrn_reflns_theta_max         30.588
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6055
_reflns_number_gt                4733
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.858
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_fraction_full    0.999

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 TITL p21fin in P2(1)
CELL 0.71073 10.5665 7.6596 12.8714 90.000 106.949 90.000
ZERR 2.0000 0.0010 0.0007 0.0011 0.000 0.002 0.000
LATT -1
SYMM -X, 0.5+Y, -Z
SFAC C H N O
UNIT 36 56 4 16
MERG 2
FMAP 2
GRID
PLAN 20
TEMP -100
SIZE 0.08 0.11 0.24
DFIX 0.86 0.02 OW1 H1W1
DFIX 0.86 0.02 OW1 H2W1
DANG 1.36 0.04 H1W1 H2W1
DFIX 0.86 0.02 OW2 H1W2
DFIX 0.86 0.02 OW2 H2W2
DANG 1.36 0.04 H1W2 H2W2
DFIX 0.87 0.02 N2 H2N
DFIX 0.82 0.02 O3 H3O
DFIX 0.82 0.02 O6 H6O
DFIX 0.87 0.02 N1 H1N
DFIX 1.85 0.02 C7 H1N
L.S. 20
WGHT 0.09530 1.60570 0.00000 0.00000 0.00000 0.33330
FVAR 0.31542 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0950P)²+1.6055P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1839 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.1(7)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         6055
_refine_ls_number_parameters     286
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0816
_refine_ls_wR_factor_ref         0.2254
_refine_ls_wR_factor_gt          0.2045
_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

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
OW1 O 0.6472(4) 0.0498(5) 0.9695(3) 0.0297(8) Uani 1 1 d D . . . .
OW2 O 0.3479(4) 1.0909(6) 0.5294(3) 0.0332(9) Uani 1 1 d D . . . .
O1 O 0.6628(4) 0.1399(5) 0.7683(3) 0.0344(9) Uani 1 1 d . . . . .
O4 O 0.3266(4) 0.9887(5) 0.7252(3) 0.0301(8) Uani 1 1 d . . . . .
O6 O 0.2099(4) 1.2758(5) 0.9438(4) 0.0313(8) Uani 1 1 d D . . . .
H6O H 0.265(6) 1.348(8) 0.976(5) 0.047 Uiso 1 1 d D U . . .
O3 O 0.7884(4) -0.1352(6) 0.5566(4) 0.0463(12) Uani 1 1 d D . . . .
C14 C 0.1891(4) 0.9928(5) 0.8680(3) 0.0163(7) Uani 1 1 d . . . . .
H14 H 0.1485 1.0444 0.7944 0.020 Uiso 1 1 calc R U . . .
C5 C 0.5302(5) 0.7353(6) 0.7363(4) 0.0220(9) Uani 1 1 d . . . . .
H5 H 0.5551 0.8522 0.7270 0.026 Uiso 1 1 calc R U . . .
O5 O 0.3957(4) 1.1195(6) 0.9799(3) 0.0337(9) Uani 1 1 d . . . . .
C9 C 0.7132(6) 0.0008(8) 0.5607(5) 0.0317(11) Uani 1 1 d . . . . .
O2 O 0.5966(4) -0.0008(7) 0.5244(3) 0.0444(11) Uani 1 1 d . . . . .
C3 C 0.3794(5) 0.5320(6) 0.7811(4) 0.0228(9) Uani 1 1 d . . . . .
H3 H 0.3018 0.5103 0.8022 0.027 Uiso 1 1 calc R U . . .
C1 C 0.5704(5) 0.4259(6) 0.7323(4) 0.0201(8) Uani 1 1 d . . . . .
C2 C 0.4566(5) 0.3926(6) 0.7640(4) 0.0228(9) Uani 1 1 d . . . . .
H2 H 0.4320 0.2758 0.7739 0.027 Uiso 1 1 calc R U . . .
C6 C 0.6065(5) 0.5986(7) 0.7193(4) 0.0224(9) Uani 1 1 d . . . . .
H6 H 0.6841 0.6216 0.6986 0.027 Uiso 1 1 calc R U . . .
C4 C 0.4168(5) 0.7026(6) 0.7670(4) 0.0213(9) Uani 1 1 d . . . . .
C15 C 0.2778(4) 1.1326(7) 0.9386(4) 0.0230(9) Uani 1 1 d . . . . .
C12 C 0.8833(9) 0.2352(16) 0.4757(8) 0.074(3) Uani 1 1 d . . . . .
H12A H 0.8425 0.3510 0.4612 0.111 Uiso 1 1 calc R U . . .
H12B H 0.8214 0.1470 0.4350 0.111 Uiso 1 1 calc R U . . .
H12C H 0.9642 0.2330 0.4531 0.111 Uiso 1 1 calc R U . . .
C7 C 0.6497(5) 0.2755(6) 0.7131(4) 0.0250(9) Uani 1 1 d D . . . .
C13 C 0.3342(5) 0.8569(6) 0.7806(4) 0.0230(9) Uani 1 1 d . . . . .
N2 N 0.2684(4) 0.8450(5) 0.8552(3) 0.0216(7) Uani 1 1 d D . . . .
N1 N 0.7082(8) 0.2928(7) 0.6364(7) 0.064(2) Uani 1 1 d D . . . .
C17 C -0.0097(5) 0.7963(8) 0.8439(5) 0.0338(11) Uani 1 1 d . . . . .
H17A H -0.0945 0.7872 0.8601 0.051 Uiso 1 1 calc R U . . .
H17B H 0.0369 0.6842 0.8590 0.051 Uiso 1 1 calc R U . . .
H17C H -0.0255 0.8263 0.7671 0.051 Uiso 1 1 calc R U . . .
C8 C 0.7908(12) 0.1594(14) 0.6111(15) 0.163(8) Uani 1 1 d . . . . .
H8 H 0.8204 0.1100 0.6862 0.196 Uiso 1 1 calc R U . . .
C16 C 0.0746(5) 0.9383(7) 0.9147(4) 0.0246(9) Uani 1 1 d . . . . .
H16 H 0.0165 1.0429 0.9096 0.029 Uiso 1 1 calc R U . . .
C10 C 0.9198(7) 0.1933(8) 0.6050(7) 0.067(3) Uani 1 1 d . . . . .
H10 H 0.9780 0.0881 0.6250 0.080 Uiso 1 1 calc R U . . .
C18 C 0.1221(5) 0.8862(8) 1.0344(4) 0.0308(10) Uani 1 1 d . . . . .
H18A H 0.1749 0.7792 1.0423 0.046 Uiso 1 1 calc R U . . .
H18B H 0.0455 0.8658 1.0611 0.046 Uiso 1 1 calc R U . . .
H18C H 0.1764 0.9802 1.0765 0.046 Uiso 1 1 calc R U . . .
C11 C 0.9839(13) 0.3540(14) 0.6688(8) 0.116(5) Uani 1 1 d . . . . .
H11A H 1.0172 0.3246 0.7461 0.174 Uiso 1 1 calc R U . . .
H11B H 0.9183 0.4476 0.6586 0.174 Uiso 1 1 calc R U . . .
H11C H 1.0575 0.3930 0.6426 0.174 Uiso 1 1 calc R U . . .
H1W2 H 0.359(4) 1.057(6) 0.594(2) 0.007(10) Uiso 1 1 d D . . . .
H2W1 H 0.563(3) 0.059(9) 0.961(5) 0.036(17) Uiso 1 1 d D . . . .
H1W1 H 0.667(9) 0.068(18) 0.910(5) 0.13(5) Uiso 1 1 d D . . . .
H2W2 H 0.414(5) 1.101(15) 0.508(6) 0.08(3) Uiso 1 1 d D . . . .
H2N H 0.287(10) 0.750(8) 0.893(7) 0.099 Uiso 1 1 d D U . . .
H3O H 0.741(11) -0.222(11) 0.531(10) 0.124 Uiso 1 1 d D U . . .
H1N H 0.668(5) 0.355(8) 0.584(3) 0.030(18) Uiso 1 1 d 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 C7 1.243(7) . ?
O4 C13 1.225(6) . ?
O6 C15 1.323(6) . ?
O3 C9 1.321(7) . ?
C14 N2 1.446(5) . ?
C14 C15 1.535(7) . ?
C14 C16 1.557(6) . ?
C5 C6 1.378(7) . ?
C5 C4 1.389(6) . ?
O5 C15 1.207(6) . ?
C9 O2 1.183(7) . ?
C9 C8 1.503(10) . ?
C3 C4 1.393(7) . ?
C3 C2 1.400(7) . ?
C1 C6 1.400(7) . ?
C1 C2 1.401(6) . ?
C1 C7 1.487(7) . ?
C4 C13 1.509(7) . ?
C12 C10 1.627(13) . ?
C7 N1 1.316(7) . ?
C13 N2 1.343(6) . ?
N1 C8 1.441(10) . ?
C17 C16 1.528(7) . ?
C8 C10 1.412(11) . ?
C16 C18 1.527(7) . ?
C10 C11 1.524(11) . ?

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
N2 C14 C15 109.9(3) . . ?
N2 C14 C16 112.0(4) . . ?
C15 C14 C16 111.5(3) . . ?
C6 C5 C4 120.1(5) . . ?
O2 C9 O3 123.1(6) . . ?
O2 C9 C8 123.6(7) . . ?
O3 C9 C8 113.3(6) . . ?
C4 C3 C2 119.6(4) . . ?
C6 C1 C2 119.6(4) . . ?
C6 C1 C7 121.7(4) . . ?
C2 C1 C7 118.7(4) . . ?
C3 C2 C1 119.7(4) . . ?
C5 C6 C1 120.4(4) . . ?
C5 C4 C3 120.5(4) . . ?
C5 C4 C13 117.9(4) . . ?
C3 C4 C13 121.6(4) . . ?
O5 C15 O6 123.5(5) . . ?
O5 C15 C14 125.2(5) . . ?
O6 C15 C14 111.2(4) . . ?
O1 C7 N1 121.0(5) . . ?
O1 C7 C1 121.8(4) . . ?
N1 C7 C1 117.2(5) . . ?
O4 C13 N2 120.7(4) . . ?
O4 C13 C4 121.4(4) . . ?
N2 C13 C4 117.9(4) . . ?
C13 N2 C14 117.8(4) . . ?
C7 N1 C8 123.1(9) . . ?
C10 C8 N1 122.7(7) . . ?
C10 C8 C9 122.6(6) . . ?
N1 C8 C9 112.4(7) . . ?
C18 C16 C17 112.3(5) . . ?
C18 C16 C14 113.3(4) . . ?
C17 C16 C14 110.1(4) . . ?
C8 C10 C11 113.7(10) . . ?
C8 C10 C12 98.5(9) . . ?
C11 C10 C12 109.1(7) . . ?

_refine_diff_density_max         1.532
_refine_diff_density_min         -0.888
_refine_diff_density_rms         0.088

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 993039'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H21.57 N3 O9.28'
_chemical_formula_weight         428.48

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           trigonal
_symmetry_space_group_name_H-M   'R -3'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   18.3488(5)
_cell_length_b                   18.3488(5)
_cell_length_c                   11.1379(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     3247.5(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3268
_cell_measurement_theta_min      3.1445
_cell_measurement_theta_max      30.2990

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1349
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   SABADS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.5467
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1468
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.85
_diffrn_reflns_theta_max         26.36
_reflns_number_total             1468
_reflns_number_gt                1348
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.6 (release 27-01-2011 CrysAlis171 .NET)
(compiled Jan 27 2011,13:34:29)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.6 (release 27-01-2011 CrysAlis171 .NET)
(compiled Jan 27 2011,13:34:29)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.6 (release 27-01-2011 CrysAlis171 .NET)
(compiled Jan 27 2011,13:34:29)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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.
During the refinement, the restraint command 'DFIX' was also used to refine
the distances of one N-H bond and one O-H bond of this compound. These atoms are
as follows: N2 H2A O3 H3A. The restraint commands 'EXYZ' and 'EADP' were also 
used to refine C4A and C4B carbon atoms which had ADP problems.
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.333 0.667 0.167 105 10 ' '
2 0.000 0.000 0.500 108 10 ' '
3 0.667 0.333 0.833 105 10 ' '
_platon_squeeze_details          
;
Attempts to refine peaks of residual electron density as guest
atoms were unsuccessful. The data were corrected for disordered
electron density through use of the SQUEEZE procedure (Sluis, P. van der;
Spek, A. L. Acta Crystallogr. 1990, A46, 194-201) as implemented in PLATON
(Spek, A.L. Acta Crystallogr. 1990, A46, C34. PLATON - a multipurpose
crystallographic tool. Utrecht University, Utrecht, The Netherlands).
A total solvent-accessible void volume of 324.1 A³ with a totalm ectron count of 31 (consistent with 0.3 molecules of
water per formula) was found in the unit cell.
;

_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)+(0.0679P)²+25.4319P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1468
_refine_ls_number_parameters     112
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0889
_refine_ls_wR_factor_ref         0.2413
_refine_ls_wR_factor_gt          0.2394
_refine_ls_goodness_of_fit_ref   1.250
_refine_ls_restrained_S_all      1.249
_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
C1 C 0.6284(2) 0.3819(2) 0.4925(3) 0.0253(8) Uani 1 1 d . . .
H1 H 0.6029 0.4147 0.4930 0.045(13) Uiso 1 1 calc R . .
C2 C 0.5789(2) 0.2951(2) 0.4921(3) 0.0257(8) Uani 1 1 d . . .
C3 C 0.4851(2) 0.2575(2) 0.4855(3) 0.0274(8) Uani 1 1 d . A .
C5A C 0.3067(6) 0.0476(6) 0.3976(11) 0.052(3) Uani 0.490(13) 1 d P A 1
H5A1 H 0.3429 0.0373 0.3470 0.062 Uiso 0.490(13) 1 calc PR A 1
H5A2 H 0.2552 0.0320 0.3558 0.062 Uiso 0.490(13) 1 calc PR A 1
H5A3 H 0.2946 0.0150 0.4697 0.062 Uiso 0.490(13) 1 calc PR A 1
C5B C 0.3020(6) 0.1129(8) 0.5410(11) 0.068(4) Uani 0.510(13) 1 d P A 2
H5B1 H 0.3121 0.1622 0.5847 0.082 Uiso 0.510(13) 1 calc PR A 2
H5B2 H 0.3201 0.0811 0.5883 0.082 Uiso 0.510(13) 1 calc PR A 2
H5B3 H 0.2430 0.0790 0.5242 0.082 Uiso 0.510(13) 1 calc PR A 2
C6 C 0.3273(2) 0.1853(2) 0.3356(4) 0.0333(9) Uani 1 1 d . . .
H2A H 0.461(3) 0.145(3) 0.433(4) 0.045(13) Uiso 1 1 d D . .
H3A H 0.241(4) 0.200(3) 0.290(4) 0.060(16) Uiso 1 1 d D . .
N2 N 0.4408(2) 0.1788(2) 0.4440(3) 0.0337(8) Uani 1 1 d D . .
O1 O 0.45110(18) 0.29822(19) 0.5131(3) 0.0417(8) Uani 1 1 d . . .
O2 O 0.37626(18) 0.23532(19) 0.2643(3) 0.0442(8) Uani 1 1 d . A .
O3 O 0.24760(19) 0.1617(2) 0.3420(3) 0.0468(9) Uani 1 1 d D A .
C4A C 0.3489(2) 0.1379(3) 0.4285(4) 0.0392(10) Uani 0.490(13) 1 d P A 1
H4A H 0.3255 0.1425 0.5054 0.047 Uiso 0.490(13) 1 calc PR A 1
C4B C 0.3489(2) 0.1379(3) 0.4285(4) 0.0392(10) Uani 0.510(13) 1 d P A 2
H4B H 0.3337 0.0844 0.3891 0.047 Uiso 0.510(13) 1 calc PR A 2


_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 1.384(5) . ?
C1 C2 1.397(5) 3_665 ?
C2 C1 1.397(5) 2_655 ?
C2 C3 1.503(5) . ?
C3 O1 1.228(5) . ?
C3 N2 1.336(5) . ?
C5A C4A 1.477(10) . ?
C6 O2 1.206(5) . ?
C6 O3 1.304(5) . ?
C6 C4A 1.525(6) . ?
N2 C4A 1.473(5) . ?

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 C2 121.1(3) . 3_665 ?
C1 C2 C1 118.9(3) . 2_655 ?
C1 C2 C3 118.1(3) . . ?
C1 C2 C3 122.9(3) 2_655 . ?
O1 C3 N2 121.6(3) . . ?
O1 C3 C2 121.4(3) . . ?
N2 C3 C2 116.9(3) . . ?
O2 C6 O3 125.0(4) . . ?
O2 C6 C4A 125.0(4) . . ?
O3 C6 C4A 110.0(4) . . ?
C3 N2 C4A 120.9(3) . . ?
N2 C4A C5A 115.0(5) . . ?
N2 C4A C6 110.2(3) . . ?
C5A C4A C6 110.0(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
N2 H2A O2 0.875(19) 2.03(2) 2.888(4) 165(5) 18_545
O3 H3A O1 0.96(2) 1.77(3) 2.641(4) 149(5) 9_554

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.36
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.085


_database_code_depnum_ccdc_archive 'CCDC 993040'
