# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1444163'
_audit_update_record             
;
2015-12-24 deposited with the CCDC.
2016-01-15 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         ?
_chemical_formula_sum            'C27 H30 N2 O5'
_chemical_formula_weight         462.53

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.116(3)
_cell_length_b                   11.260(3)
_cell_length_c                   11.711(3)
_cell_angle_alpha                63.523(15)
_cell_angle_beta                 71.584(17)
_cell_angle_gamma                69.128(17)
_cell_volume                     1204.2(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3562
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      29.10

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            12275
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.064
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4222
_reflns_number_gt                3492
_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 2.1 b28 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b28'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b28'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'WinGX v2014.1'
_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)+(0.0481P)²+0.2203P] 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_number_reflns         4222
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.0969
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.52840(10) 0.20243(10) 0.40542(10) 0.0243(3) Uani 1 1 d . . . . .
O1 O 0.13753(10) 0.12167(10) 0.64219(10) 0.0242(3) Uani 1 1 d . . . . .
O3 O 0.34072(11) 0.37294(11) 0.38796(11) 0.0320(3) Uani 1 1 d . . . . .
O4 O 0.50362(11) 0.15279(11) 0.70361(11) 0.0305(3) Uani 1 1 d . . . . .
O5 O 0.56416(11) -0.07699(11) 0.75226(12) 0.0320(3) Uani 1 1 d . . . . .
N2 N 0.40797(13) 0.05044(13) 0.63772(12) 0.0215(3) Uani 1 1 d . . . . .
N1 N 0.34124(12) 0.17382(12) 0.55642(12) 0.0212(3) Uani 1 1 d . . . . .
C13 C 0.16912(15) 0.41496(15) 0.68044(14) 0.0211(4) Uani 1 1 d . . . . .
C20 C 0.41341(15) 0.24755(15) 0.44455(14) 0.0213(3) Uani 1 1 d . . . . .
C24 C 0.49471(15) 0.05224(15) 0.69809(14) 0.0221(4) Uani 1 1 d . . . . .
C10 C 0.05307(15) 0.21555(15) 0.79896(14) 0.0218(4) Uani 1 1 d . . . . .
C6 C -0.03643(15) 0.23256(16) 0.91152(15) 0.0238(4) Uani 1 1 d . . . . .
C11 C 0.17566(15) 0.26411(15) 0.72519(14) 0.0205(3) Uani 1 1 d . . . . .
C9 C 0.04124(16) 0.13314(15) 0.74816(15) 0.0232(4) Uani 1 1 d . . . . .
C18 C 0.27705(16) 0.45484(16) 0.67093(16) 0.0255(4) Uani 1 1 d . . . . .
H18 H 0.3531 0.3872 0.7000 0.031 Uiso 1 1 calc R U . . .
C12 C 0.20522(15) 0.22571(15) 0.60579(15) 0.0212(3) Uani 1 1 d . . . . .
C16 C 0.16594(16) 0.69451(16) 0.57730(15) 0.0260(4) Uani 1 1 d . . . . .
C1 C -0.02883(17) 0.31293(17) 0.97273(15) 0.0290(4) Uani 1 1 d . . . . .
H1 H 0.0382 0.3602 0.9377 0.035 Uiso 1 1 calc R U . . .
C5 C -0.13775(16) 0.16225(16) 0.96525(15) 0.0268(4) Uani 1 1 d . . . . .
C17 C 0.27574(17) 0.59273(16) 0.61931(16) 0.0281(4) Uani 1 1 d . . . . .
H17 H 0.3514 0.6178 0.6126 0.034 Uiso 1 1 calc R U . . .
C15 C 0.05738(17) 0.65364(16) 0.58809(16) 0.0280(4) Uani 1 1 d . . . . .
H15 H -0.0192 0.7213 0.5603 0.034 Uiso 1 1 calc R U . . .
C14 C 0.05862(16) 0.51607(16) 0.63869(16) 0.0268(4) Uani 1 1 d . . . . .
H14 H -0.0168 0.4907 0.6449 0.032 Uiso 1 1 calc R U . . .
C8 C -0.05698(16) 0.06217(16) 0.79998(16) 0.0273(4) Uani 1 1 d . . . . .
H8 H -0.0624 0.0056 0.7621 0.033 Uiso 1 1 calc R U . . .
C7 C -0.14478(16) 0.07822(17) 0.90779(16) 0.0306(4) Uani 1 1 d . . . . .
H7 H -0.2125 0.0316 0.9452 0.037 Uiso 1 1 calc R U . . .
C21 C 0.40290(17) 0.46884(16) 0.26904(15) 0.0288(4) Uani 1 1 d . . . . .
H21 H 0.5003 0.4378 0.2617 0.035 Uiso 1 1 calc R U . . .
C4 C -0.22824(17) 0.17701(18) 1.07786(16) 0.0346(4) Uani 1 1 d . . . . .
H4 H -0.2971 0.1319 1.1142 0.042 Uiso 1 1 calc R U . . .
C25 C 0.65964(17) -0.09880(17) 0.82592(18) 0.0347(4) Uani 1 1 d . . . . .
H25 H 0.6690 -0.0083 0.8128 0.042 Uiso 1 1 calc R U . . .
C3 C -0.21810(18) 0.25496(19) 1.13498(17) 0.0378(5) Uani 1 1 d . . . . .
H3 H -0.2793 0.2631 1.2106 0.045 Uiso 1 1 calc R U . . .
C19 C 0.16578(19) 0.84391(16) 0.52061(18) 0.0379(5) Uani 1 1 d . . . . .
H19A H 0.0806 0.9005 0.4965 0.057 Uiso 1 1 calc R U . . .
H19B H 0.1815 0.8670 0.5852 0.057 Uiso 1 1 calc R U . . .
H19C H 0.2351 0.8613 0.4433 0.057 Uiso 1 1 calc R U . . .
C2 C -0.11785(17) 0.32273(19) 1.08234(16) 0.0355(4) Uani 1 1 d . . . . .
H2 H -0.1113 0.3762 1.1229 0.043 Uiso 1 1 calc R U . . .
C23 C 0.3664(2) 0.4705(2) 0.15539(18) 0.0468(5) Uani 1 1 d . . . . .
H23A H 0.4067 0.5338 0.0748 0.070 Uiso 1 1 calc R U . . .
H23B H 0.3978 0.3780 0.1538 0.070 Uiso 1 1 calc R U . . .
H23C H 0.2709 0.5008 0.1633 0.070 Uiso 1 1 calc R U . . .
C22 C 0.3522(2) 0.60520(19) 0.28319(19) 0.0476(5) Uani 1 1 d . . . . .
H22A H 0.3908 0.6734 0.2061 0.071 Uiso 1 1 calc R U . . .
H22B H 0.2566 0.6340 0.2923 0.071 Uiso 1 1 calc R U . . .
H22C H 0.3762 0.5972 0.3604 0.071 Uiso 1 1 calc R U . . .
C26 C 0.78763(19) -0.17874(19) 0.7717(2) 0.0486(5) Uani 1 1 d . . . . .
H26A H 0.8553 -0.1961 0.8182 0.073 Uiso 1 1 calc R U . . .
H26B H 0.7775 -0.2663 0.7824 0.073 Uiso 1 1 calc R U . . .
H26C H 0.8134 -0.1259 0.6792 0.073 Uiso 1 1 calc R U . . .
C27 C 0.6091(3) -0.1732(2) 0.9680(2) 0.0608(7) Uani 1 1 d . . . . .
H27A H 0.6716 -0.1891 1.0197 0.091 Uiso 1 1 calc R U . . .
H27B H 0.5241 -0.1173 0.9960 0.091 Uiso 1 1 calc R U . . .
H27C H 0.5989 -0.2613 0.9805 0.091 Uiso 1 1 calc R U . . .
H1N H 0.4231(17) -0.0218(17) 0.6197(16) 0.029(5) Uiso 1 1 d . . . . .
H12A H 0.1694(15) 0.3082(16) 0.5325(15) 0.019(4) Uiso 1 1 d . . . . .
H11A H 0.2486(16) 0.2095(15) 0.7736(15) 0.020(4) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C20 1.2152(18) . ?
O1 C9 1.3812(19) . ?
O1 C12 1.4493(19) . ?
O3 C20 1.3330(18) . ?
O3 C21 1.4717(19) . ?
O4 C24 1.2022(18) . ?
O5 C24 1.3423(18) . ?
O5 C25 1.461(2) . ?
N2 C24 1.374(2) . ?
N2 N1 1.3853(17) . ?
N2 H1N 0.876(17) . ?
N1 C20 1.375(2) . ?
N1 C12 1.443(2) . ?
C13 C18 1.381(2) . ?
C13 C14 1.389(2) . ?
C13 C11 1.519(2) . ?
C10 C9 1.364(2) . ?
C10 C6 1.423(2) . ?
C10 C11 1.506(2) . ?
C6 C1 1.418(2) . ?
C6 C5 1.426(2) . ?
C11 C12 1.548(2) . ?
C11 H11A 0.991(16) . ?
C9 C8 1.403(2) . ?
C18 C17 1.389(2) . ?
C18 H18 0.9500 . ?
C12 H12A 0.999(16) . ?
C16 C17 1.388(2) . ?
C16 C15 1.390(2) . ?
C16 C19 1.508(2) . ?
C1 C2 1.373(2) . ?
C1 H1 0.9500 . ?
C5 C7 1.417(2) . ?
C5 C4 1.420(2) . ?
C17 H17 0.9500 . ?
C15 C14 1.387(2) . ?
C15 H15 0.9500 . ?
C14 H14 0.9500 . ?
C8 C7 1.371(2) . ?
C8 H8 0.9500 . ?
C7 H7 0.9500 . ?
C21 C23 1.500(3) . ?
C21 C22 1.501(2) . ?
C21 H21 1.0000 . ?
C4 C3 1.368(3) . ?
C4 H4 0.9500 . ?
C25 C26 1.505(3) . ?
C25 C27 1.513(3) . ?
C25 H25 1.0000 . ?
C3 C2 1.399(3) . ?
C3 H3 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C2 H2 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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 O1 C12 105.43(11) . . ?
C20 O3 C21 118.67(12) . . ?
C24 O5 C25 117.32(13) . . ?
C24 N2 N1 118.72(13) . . ?
C24 N2 H1N 118.1(11) . . ?
N1 N2 H1N 116.6(11) . . ?
C20 N1 N2 117.70(12) . . ?
C20 N1 C12 124.40(13) . . ?
N2 N1 C12 117.07(12) . . ?
C18 C13 C14 118.45(14) . . ?
C18 C13 C11 120.44(14) . . ?
C14 C13 C11 120.93(14) . . ?
O2 C20 O3 125.74(14) . . ?
O2 C20 N1 123.37(14) . . ?
O3 C20 N1 110.89(13) . . ?
O4 C24 O5 126.33(15) . . ?
O4 C24 N2 125.25(14) . . ?
O5 C24 N2 108.39(13) . . ?
C9 C10 C6 120.16(15) . . ?
C9 C10 C11 108.64(13) . . ?
C6 C10 C11 130.93(15) . . ?
C1 C6 C10 123.78(16) . . ?
C1 C6 C5 119.14(15) . . ?
C10 C6 C5 117.07(15) . . ?
C10 C11 C13 118.89(13) . . ?
C10 C11 C12 100.06(13) . . ?
C13 C11 C12 109.77(12) . . ?
C10 C11 H11A 111.1(9) . . ?
C13 C11 H11A 108.1(9) . . ?
C12 C11 H11A 108.3(9) . . ?
C10 C9 O1 114.04(14) . . ?
C10 C9 C8 123.74(15) . . ?
O1 C9 C8 122.19(15) . . ?
C13 C18 C17 120.78(15) . . ?
C13 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
N1 C12 O1 107.89(11) . . ?
N1 C12 C11 116.72(13) . . ?
O1 C12 C11 107.28(12) . . ?
N1 C12 H12A 106.9(9) . . ?
O1 C12 H12A 108.6(9) . . ?
C11 C12 H12A 109.3(8) . . ?
C17 C16 C15 117.65(15) . . ?
C17 C16 C19 120.85(16) . . ?
C15 C16 C19 121.50(15) . . ?
C2 C1 C6 120.35(17) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C7 C5 C4 121.67(16) . . ?
C7 C5 C6 120.03(15) . . ?
C4 C5 C6 118.29(16) . . ?
C16 C17 C18 121.24(16) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C14 C15 C16 121.29(15) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C14 C13 120.59(16) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C7 C8 C9 116.94(16) . . ?
C7 C8 H8 121.5 . . ?
C9 C8 H8 121.5 . . ?
C8 C7 C5 122.06(16) . . ?
C8 C7 H7 119.0 . . ?
C5 C7 H7 119.0 . . ?
O3 C21 C23 107.87(15) . . ?
O3 C21 C22 106.01(14) . . ?
C23 C21 C22 113.09(15) . . ?
O3 C21 H21 109.9 . . ?
C23 C21 H21 109.9 . . ?
C22 C21 H21 109.9 . . ?
C3 C4 C5 121.20(18) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
O5 C25 C26 106.29(15) . . ?
O5 C25 C27 107.87(16) . . ?
C26 C25 C27 113.74(17) . . ?
O5 C25 H25 109.6 . . ?
C26 C25 H25 109.6 . . ?
C27 C25 H25 109.6 . . ?
C4 C3 C2 120.18(16) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 C2 C3 120.83(18) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

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
C24 N2 N1 C20 65.56(18) . . . . ?
C24 N2 N1 C12 -104.45(16) . . . . ?
C21 O3 C20 O2 -1.5(2) . . . . ?
C21 O3 C20 N1 177.79(13) . . . . ?
N2 N1 C20 O2 9.9(2) . . . . ?
C12 N1 C20 O2 179.11(14) . . . . ?
N2 N1 C20 O3 -169.37(12) . . . . ?
C12 N1 C20 O3 -0.2(2) . . . . ?
C25 O5 C24 O4 0.4(2) . . . . ?
C25 O5 C24 N2 -177.88(13) . . . . ?
N1 N2 C24 O4 12.6(2) . . . . ?
N1 N2 C24 O5 -169.16(12) . . . . ?
C9 C10 C6 C1 178.07(14) . . . . ?
C11 C10 C6 C1 4.8(3) . . . . ?
C9 C10 C6 C5 -1.0(2) . . . . ?
C11 C10 C6 C5 -174.27(15) . . . . ?
C9 C10 C11 C13 133.74(14) . . . . ?
C6 C10 C11 C13 -52.4(2) . . . . ?
C9 C10 C11 C12 14.38(16) . . . . ?
C6 C10 C11 C12 -171.79(15) . . . . ?
C18 C13 C11 C10 148.83(15) . . . . ?
C14 C13 C11 C10 -36.2(2) . . . . ?
C18 C13 C11 C12 -96.95(17) . . . . ?
C14 C13 C11 C12 78.01(17) . . . . ?
C6 C10 C9 O1 -177.57(13) . . . . ?
C11 C10 C9 O1 -2.96(18) . . . . ?
C6 C10 C9 C8 0.6(2) . . . . ?
C11 C10 C9 C8 175.19(14) . . . . ?
C12 O1 C9 C10 -11.02(16) . . . . ?
C12 O1 C9 C8 170.80(14) . . . . ?
C14 C13 C18 C17 -0.8(2) . . . . ?
C11 C13 C18 C17 174.27(14) . . . . ?
C20 N1 C12 O1 133.90(14) . . . . ?
N2 N1 C12 O1 -56.83(16) . . . . ?
C20 N1 C12 C11 -105.31(17) . . . . ?
N2 N1 C12 C11 63.97(17) . . . . ?
C9 O1 C12 N1 146.51(12) . . . . ?
C9 O1 C12 C11 19.99(15) . . . . ?
C10 C11 C12 N1 -141.87(13) . . . . ?
C13 C11 C12 N1 92.31(16) . . . . ?
C10 C11 C12 O1 -20.76(15) . . . . ?
C13 C11 C12 O1 -146.58(12) . . . . ?
C10 C6 C1 C2 -179.03(15) . . . . ?
C5 C6 C1 C2 0.1(2) . . . . ?
C1 C6 C5 C7 -178.16(14) . . . . ?
C10 C6 C5 C7 1.0(2) . . . . ?
C1 C6 C5 C4 0.7(2) . . . . ?
C10 C6 C5 C4 179.80(13) . . . . ?
C15 C16 C17 C18 -0.3(2) . . . . ?
C19 C16 C17 C18 -179.61(15) . . . . ?
C13 C18 C17 C16 0.8(2) . . . . ?
C17 C16 C15 C14 -0.2(2) . . . . ?
C19 C16 C15 C14 179.12(15) . . . . ?
C16 C15 C14 C13 0.2(2) . . . . ?
C18 C13 C14 C15 0.3(2) . . . . ?
C11 C13 C14 C15 -174.72(14) . . . . ?
C10 C9 C8 C7 0.0(2) . . . . ?
O1 C9 C8 C7 177.98(13) . . . . ?
C9 C8 C7 C5 0.0(2) . . . . ?
C4 C5 C7 C8 -179.25(15) . . . . ?
C6 C5 C7 C8 -0.5(2) . . . . ?
C20 O3 C21 C23 100.83(17) . . . . ?
C20 O3 C21 C22 -137.75(16) . . . . ?
C7 C5 C4 C3 177.91(15) . . . . ?
C6 C5 C4 C3 -0.9(2) . . . . ?
C24 O5 C25 C26 -127.47(15) . . . . ?
C24 O5 C25 C27 110.18(17) . . . . ?
C5 C4 C3 C2 0.4(3) . . . . ?
C6 C1 C2 C3 -0.6(2) . . . . ?
C4 C3 C2 C1 0.3(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
N2 H1N O2 0.876(17) 2.041(18) 2.9128(19) 173.2(16) 2_656
N2 H1N O2 0.876(17) 2.041(18) 2.9128(19) 173.2(16) 2_656
C11 H11A O4 0.991(16) 2.612(16) 3.372(2) 133.5(11) .

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_INN-MVD-CYCLOHEXYL
_database_code_depnum_ccdc_archive 'CCDC 1444164'
_audit_update_record             
;
2015-12-24 deposited with the CCDC.
2016-01-15 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H27 N3 O6'
_chemical_formula_moiety         'C16 H27 N3 O6'
_chemical_formula_weight         357.41
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.777(5)
_cell_length_b                   10.159(5)
_cell_length_c                   10.306(5)
_cell_angle_alpha                102.265(7)
_cell_angle_beta                 100.480(6)
_cell_angle_gamma                90.508(8)
_cell_volume                     982.4(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3091
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      29.30
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.130
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384.00
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.988

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            17916
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_theta_max         29.30
_diffrn_reflns_theta_full        29.30
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             5353
_reflns_number_gt                2442
_reflns_threshold_expression     F>2.0σ(F)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1670
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5353
_refine_ls_number_parameters     226
_refine_ls_goodness_of_fit_ref   0.733
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.075
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.29945(12) 0.56324(13) 0.51513(13) 0.0337(4) Uani 1.0 2 d . . .
O2 O 0.25335(12) 0.59235(12) 0.72782(13) 0.0303(3) Uani 1.0 2 d . . .
O3 O 0.26486(12) 0.19814(13) 0.46394(14) 0.0369(4) Uani 1.0 2 d . . .
O4 O 0.46069(12) 0.19537(13) 0.37311(13) 0.0340(4) Uani 1.0 2 d . . .
O7 O 0.60932(13) 0.50073(14) 0.82396(15) 0.0422(4) Uani 1.0 2 d . . .
O9 O 0.57753(14) 0.36324(14) 0.95307(15) 0.0416(4) Uani 1.0 2 d . . .
N5 N 0.44946(14) 0.34840(16) 0.55776(16) 0.0321(4) Uani 1.0 2 d . . .
N6 N 0.37707(14) 0.41954(15) 0.65241(15) 0.0272(4) Uani 1.0 2 d . . .
N8 N 0.53863(15) 0.41755(16) 0.85687(17) 0.0320(4) Uani 1.0 2 d . . .
C10 C 0.37950(17) 0.24299(17) 0.46321(18) 0.0264(4) Uani 1.0 2 d . . .
C11 C 0.30815(16) 0.53123(18) 0.62332(18) 0.0268(4) Uani 1.0 2 d . . .
C12 C 0.39561(16) 0.38240(17) 0.77696(18) 0.0258(4) Uani 1.0 2 d . . .
C13 C 0.15161(17) 0.29502(18) 0.76315(19) 0.0281(4) Uani 1.0 2 d . . .
C14 C 0.30103(17) 0.32544(17) 0.82832(19) 0.0274(4) Uani 1.0 2 d . . .
C15 C 0.1125(2) 0.14298(18) 0.7301(3) 0.0366(5) Uani 1.0 2 d . . .
C16 C 0.17513(19) 0.71279(18) 0.7129(2) 0.0326(5) Uani 1.0 2 d . . .
C17 C 0.05977(18) 0.37162(19) 0.8576(2) 0.0340(5) Uani 1.0 2 d . . .
C18 C 0.3990(2) 0.08618(18) 0.2598(2) 0.0366(5) Uani 1.0 2 d . . .
C19 C -0.0420(2) 0.1164(2) 0.6655(3) 0.0430(6) Uani 1.0 2 d . . .
C20 C -0.09441(19) 0.3456(2) 0.7940(3) 0.0434(6) Uani 1.0 2 d . . .
C21 C 0.0317(2) 0.6699(3) 0.6328(3) 0.0477(6) Uani 1.0 2 d . . .
C22 C 0.1752(3) 0.7880(2) 0.8557(3) 0.0474(6) Uani 1.0 2 d . . .
C23 C 0.3476(4) 0.1474(3) 0.1416(3) 0.0837(10) Uani 1.0 2 d . . .
C24 C -0.1348(2) 0.1949(3) 0.7562(3) 0.0471(6) Uani 1.0 2 d . . .
C25 C 0.5106(3) -0.0114(3) 0.2366(3) 0.0633(8) Uani 1.0 2 d . . .
H5 H 0.5350 0.3700 0.5587 0.0386 Uiso 1.0 2 calc R . .
H13 H 0.1349 0.3272 0.6787 0.0337 Uiso 1.0 2 calc R . .
H14 H 0.3303 0.3028 0.9114 0.0329 Uiso 1.0 2 calc R . .
H15A H 0.1312 0.1090 0.8124 0.0439 Uiso 1.0 2 calc R . .
H15B H 0.1689 0.0957 0.6685 0.0439 Uiso 1.0 2 calc R . .
H16 H 0.2234 0.7682 0.6665 0.0391 Uiso 1.0 2 calc R . .
H17A H 0.0775 0.3430 0.9428 0.0408 Uiso 1.0 2 calc R . .
H17B H 0.0836 0.4675 0.8759 0.0408 Uiso 1.0 2 calc R . .
H18 H 0.3209 0.0412 0.2834 0.0439 Uiso 1.0 2 calc R . .
H19A H -0.0659 0.0207 0.6493 0.0516 Uiso 1.0 2 calc R . .
H19B H -0.0586 0.1426 0.5790 0.0516 Uiso 1.0 2 calc R . .
H20A H -0.1501 0.3909 0.8574 0.0520 Uiso 1.0 2 calc R . .
H20B H -0.1140 0.3827 0.7137 0.0520 Uiso 1.0 2 calc R . .
H21A H 0.0383 0.6236 0.5429 0.0715 Uiso 1.0 2 calc R . .
H21B H -0.0221 0.7480 0.6287 0.0715 Uiso 1.0 2 calc R . .
H21C H -0.0127 0.6108 0.6755 0.0715 Uiso 1.0 2 calc R . .
H22A H 0.2693 0.8131 0.9015 0.0711 Uiso 1.0 2 calc R . .
H22B H 0.1329 0.7312 0.9024 0.0711 Uiso 1.0 2 calc R . .
H22C H 0.1234 0.8677 0.8540 0.0711 Uiso 1.0 2 calc R . .
H23A H 0.2768 0.2089 0.1627 0.1256 Uiso 1.0 2 calc R . .
H23B H 0.3095 0.0775 0.0646 0.1256 Uiso 1.0 2 calc R . .
H23C H 0.4236 0.1952 0.1215 0.1256 Uiso 1.0 2 calc R . .
H24A H -0.2311 0.1812 0.7096 0.0566 Uiso 1.0 2 calc R . .
H24B H -0.1272 0.1604 0.8379 0.0566 Uiso 1.0 2 calc R . .
H25A H 0.5377 -0.0486 0.3151 0.0949 Uiso 1.0 2 calc R . .
H25B H 0.5897 0.0346 0.2202 0.0949 Uiso 1.0 2 calc R . .
H25C H 0.4758 -0.0827 0.1598 0.0949 Uiso 1.0 2 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b28'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b28'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'


#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O1 C11 1.215(3) yes . .
O2 C11 1.328(3) yes . .
O2 C16 1.469(3) yes . .
O3 C10 1.208(3) yes . .
O4 C10 1.346(3) yes . .
O4 C18 1.463(2) yes . .
O7 N8 1.226(3) yes . .
O9 N8 1.237(3) yes . .
N5 N6 1.391(3) yes . .
N5 C10 1.366(2) yes . .
N6 C11 1.384(3) yes . .
N6 C12 1.395(3) yes . .
N8 C12 1.486(2) yes . .
C12 C14 1.330(3) yes . .
C13 C14 1.493(3) yes . .
C13 C15 1.538(3) yes . .
C13 C17 1.538(3) yes . .
C15 C19 1.532(3) yes . .
C16 C21 1.501(3) yes . .
C16 C22 1.507(3) yes . .
C17 C20 1.527(3) yes . .
C18 C23 1.493(4) yes . .
C18 C25 1.498(4) yes . .
C19 C24 1.529(4) yes . .
C20 C24 1.527(3) yes . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C11 O2 C16 117.11(16) yes . . .
C10 O4 C18 116.40(14) yes . . .
N6 N5 C10 117.43(15) yes . . .
N5 N6 C11 118.13(17) yes . . .
N5 N6 C12 116.37(15) yes . . .
C11 N6 C12 124.93(15) yes . . .
O7 N8 O9 124.44(15) yes . . .
O7 N8 C12 117.34(17) yes . . .
O9 N8 C12 118.21(16) yes . . .
O3 C10 O4 126.08(15) yes . . .
O3 C10 N5 124.88(17) yes . . .
O4 C10 N5 109.00(15) yes . . .
O1 C11 O2 126.98(17) yes . . .
O1 C11 N6 122.82(17) yes . . .
O2 C11 N6 110.19(17) yes . . .
N6 C12 N8 112.55(16) yes . . .
N6 C12 C14 127.40(15) yes . . .
N8 C12 C14 120.02(18) yes . . .
C14 C13 C15 112.11(15) yes . . .
C14 C13 C17 109.04(14) yes . . .
C15 C13 C17 110.05(17) yes . . .
C12 C14 C13 125.19(18) yes . . .
C13 C15 C19 110.42(16) yes . . .
O2 C16 C21 109.19(15) yes . . .
O2 C16 C22 104.68(16) yes . . .
C21 C16 C22 113.28(19) yes . . .
C13 C17 C20 111.00(15) yes . . .
O4 C18 C23 107.61(17) yes . . .
O4 C18 C25 106.69(16) yes . . .
C23 C18 C25 113.4(3) yes . . .
C15 C19 C24 111.40(17) yes . . .
C17 C20 C24 111.27(17) yes . . .
C19 C24 C20 111.7(2) yes . . .



#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
