# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry B.
# 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1424322'
_audit_update_record             
;
2015-09-14 deposited with the CCDC.
2016-12-06 downloaded from the CCDC.
;
_audit_creation_date             2014-11-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H25 N O4'
_chemical_formula_sum            'C24 H25 N O4'
_chemical_formula_weight         391.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   14.8761(8)
_cell_length_b                   9.7832(8)
_cell_length_c                   29.3191(19)
_cell_angle_alpha                90
_cell_angle_beta                 102.336(6)
_cell_angle_gamma                90
_cell_volume                     4168.5(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2231
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      71.1140
_cell_measurement_theta_min      4.7690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            11323
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.777
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  -60.0000 67

#__ type_ start__ end____ width___ exp.time_
  2 omega  -35.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -19.0000   90.0000 101

#__ type_ start__ end____ width___ exp.time_
  3 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000  -90.0000 88

#__ type_ start__ end____ width___ exp.time_
  4 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
  5 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000    0.0000 74

#__ type_ start__ end____ width___ exp.time_
  6 omega  101.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  101.0000  -43.0000 77

#__ type_ start__ end____ width___ exp.time_
  7 omega   57.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -90.0000 93

#__ type_ start__ end____ width___ exp.time_
  8 omega   39.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
  9 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

#__ type_ start__ end____ width___ exp.time_
 10 omega   40.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 95

#__ type_ start__ end____ width___ exp.time_
 11 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

#__ type_ start__ end____ width___ exp.time_
 12 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
 13 omega   39.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 70

#__ type_ start__ end____ width___ exp.time_
 14 omega   87.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 91

#__ type_ start__ end____ width___ exp.time_
 15 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
 16 omega    2.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   90.0000  -97.3129 30

#__ type_ start__ end____ width___ exp.time_
 17 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  150.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0042961000
_diffrn_orient_matrix_UB_12      0.0138755000
_diffrn_orient_matrix_UB_13      -0.0527597000
_diffrn_orient_matrix_UB_21      -0.0312857000
_diffrn_orient_matrix_UB_22      0.1498278000
_diffrn_orient_matrix_UB_23      0.0016541000
_diffrn_orient_matrix_UB_31      0.1011389000
_diffrn_orient_matrix_UB_32      0.0467305000
_diffrn_orient_matrix_UB_33      0.0103226000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2507
_reflns_number_total             3723
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3723
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0735
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1190P)²+0.3800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1888
_refine_ls_wR_factor_ref         0.2221
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26),
 C27(H27), C28(H28), C29(H29)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.15117(12) 0.6224(2) 0.29316(7) 0.0631(6) Uani 1 1 d . . . . .
O2 O 0.03903(11) 0.5174(2) 0.24313(7) 0.0618(6) Uani 1 1 d . . . . .
N3 N 0.34074(13) 0.4350(3) 0.22720(8) 0.0540(6) Uani 1 1 d . . . . .
H3 H 0.3984 0.4542 0.2349 0.065 Uiso 1 1 calc R . . . .
O4 O 0.10098(14) 0.2039(2) 0.12801(7) 0.0683(6) Uani 1 1 d . . . . .
C5 C 0.28231(16) 0.5041(3) 0.24913(9) 0.0489(6) Uani 1 1 d . . . . .
C6 C 0.15366(16) 0.4187(3) 0.18707(9) 0.0500(6) Uani 1 1 d . . . . .
H6 H 0.0993 0.3658 0.1901 0.060 Uiso 1 1 calc R . . . .
C7 C 0.22350(18) 0.3213(3) 0.17450(9) 0.0518(7) Uani 1 1 d . . . . .
C8 C 0.31349(17) 0.3368(3) 0.19358(9) 0.0515(7) Uani 1 1 d . . . . .
C9 C 0.12056(17) 0.5436(3) 0.25599(9) 0.0503(6) Uani 1 1 d . . . . .
C10 C 0.33177(17) 0.5881(4) 0.28973(10) 0.0627(8) Uani 1 1 d . . . . .
H10A H 0.3161 0.5556 0.3179 0.094 Uiso 1 1 calc GR . . . .
H10B H 0.3138 0.6821 0.2849 0.094 Uiso 1 1 calc GR . . . .
H10C H 0.3970 0.5803 0.2923 0.094 Uiso 1 1 calc GR . . . .
C11 C 0.19055(16) 0.4896(3) 0.23306(8) 0.0470(6) Uani 1 1 d . . . . .
O12 O 0.24093(16) 0.1452(3) 0.12023(9) 0.0899(8) Uani 1 1 d . . . . .
C13 C 0.13462(18) 0.7452(3) 0.36030(10) 0.0614(8) Uani 1 1 d . . . . .
C14 C 0.1240(2) 0.5248(3) 0.14840(10) 0.0630(8) Uani 1 1 d . . . . .
H14A H 0.1764 0.5778 0.1449 0.095 Uiso 1 1 calc GR . . . .
H14B H 0.0784 0.5841 0.1565 0.095 Uiso 1 1 calc GR . . . .
H14C H 0.0985 0.4791 0.1196 0.095 Uiso 1 1 calc GR . . . .
C15 C 0.1928(2) 0.2152(3) 0.13904(10) 0.0593(7) Uani 1 1 d . . . . .
C16 C 0.39212(19) 0.2574(3) 0.18245(11) 0.0660(8) Uani 1 1 d . . . . .
H16A H 0.4166 0.3054 0.1593 0.099 Uiso 1 1 calc GR . . . .
H16B H 0.3709 0.1689 0.1707 0.099 Uiso 1 1 calc GR . . . .
H16C H 0.4393 0.2470 0.2102 0.099 Uiso 1 1 calc GR . . . .
C17 C 0.0837(2) 0.6695(4) 0.31857(11) 0.0737(10) Uani 1 1 d . . . . .
H17A H 0.0510 0.5926 0.3281 0.088 Uiso 1 1 calc R . . . .
H17B H 0.0394 0.7292 0.2991 0.088 Uiso 1 1 calc R . . . .
C18 C 0.0607(2) 0.1626(3) 0.04371(11) 0.0636(8) Uani 1 1 d . . . . .
C19 C 0.1185(2) 0.8825(4) 0.36539(11) 0.0686(9) Uani 1 1 d . . . . .
H19 H 0.0748 0.9275 0.3430 0.082 Uiso 1 1 calc R . . . .
C20 C 0.1665(3) 0.9532(4) 0.40320(13) 0.0774(9) Uani 1 1 d . . . . .
H20 H 0.1552 1.0460 0.4062 0.093 Uiso 1 1 calc R . . . .
C21 C 0.0639(2) 0.1062(4) 0.09143(11) 0.0753(9) Uani 1 1 d . . . . .
H21A H 0.0022 0.0805 0.0940 0.090 Uiso 1 1 calc R . . . .
H21B H 0.1016 0.0244 0.0957 0.090 Uiso 1 1 calc R . . . .
C22 C 0.1985(2) 0.6806(4) 0.39475(12) 0.0781(10) Uani 1 1 d . . . . .
H22 H 0.2096 0.5877 0.3923 0.094 Uiso 1 1 calc R . . . .
C23 C 0.2301(3) 0.8895(5) 0.43628(12) 0.0842(11) Uani 1 1 d . . . . .
H23 H 0.2633 0.9386 0.4615 0.101 Uiso 1 1 calc R . . . .
C24 C 0.1132(3) 0.1104(5) 0.01518(13) 0.0953(13) Uani 1 1 d . . . . .
H24 H 0.1550 0.0409 0.0261 0.114 Uiso 1 1 calc R . . . .
C25 C 0.2454(3) 0.7520(5) 0.43233(12) 0.0897(11) Uani 1 1 d . . . . .
H25 H 0.2879 0.7073 0.4554 0.108 Uiso 1 1 calc R . . . .
C26 C -0.0012(3) 0.2636(5) 0.02656(15) 0.0948(12) Uani 1 1 d . . . . .
H26 H -0.0387 0.2988 0.0453 0.114 Uiso 1 1 calc R . . . .
C27 C -0.0087(4) 0.3135(6) -0.0176(2) 0.1271(18) Uani 1 1 d . . . . .
H27 H -0.0503 0.3832 -0.0284 0.153 Uiso 1 1 calc R . . . .
C28 C 0.1057(4) 0.1592(7) -0.03008(16) 0.1220(19) Uani 1 1 d . . . . .
H28 H 0.1417 0.1226 -0.0494 0.146 Uiso 1 1 calc R . . . .
C29 C 0.0443(4) 0.2617(7) -0.04573(17) 0.1210(18) Uani 1 1 d . . . . .
H29 H 0.0390 0.2960 -0.0758 0.145 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.333(3) . ?
O1 C17 1.447(3) . ?
O2 C9 1.218(3) . ?
N3 C5 1.365(3) . ?
N3 C8 1.374(4) . ?
O4 C15 1.340(3) . ?
O4 C21 1.455(4) . ?
C5 C10 1.503(4) . ?
C5 C11 1.353(3) . ?
C6 C7 1.512(4) . ?
C6 C11 1.511(4) . ?
C6 C14 1.531(4) . ?
C7 C8 1.345(4) . ?
C7 C15 1.471(4) . ?
C8 C16 1.497(4) . ?
C9 C11 1.454(3) . ?
O12 C15 1.205(3) . ?
C13 C17 1.491(4) . ?
C13 C19 1.378(5) . ?
C13 C22 1.383(5) . ?
C18 C21 1.496(4) . ?
C18 C24 1.361(4) . ?
C18 C26 1.371(5) . ?
C19 C20 1.371(5) . ?
C20 C23 1.354(5) . ?
C22 C25 1.363(5) . ?
C23 C25 1.374(6) . ?
C24 C28 1.392(6) . ?
C26 C27 1.366(6) . ?
C27 C29 1.356(7) . ?
C28 C29 1.367(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
C9 O1 C17 116.9(2) . . ?
C5 N3 C8 124.3(2) . . ?
C15 O4 C21 116.0(2) . . ?
N3 C5 C10 113.0(2) . . ?
C11 C5 N3 118.7(2) . . ?
C11 C5 C10 128.3(2) . . ?
C7 C6 C14 110.6(2) . . ?
C11 C6 C7 111.7(2) . . ?
C11 C6 C14 110.0(2) . . ?
C8 C7 C6 120.2(2) . . ?
C8 C7 C15 120.3(3) . . ?
C15 C7 C6 119.4(2) . . ?
N3 C8 C16 113.2(2) . . ?
C7 C8 N3 119.5(2) . . ?
C7 C8 C16 127.3(3) . . ?
O1 C9 C11 115.8(2) . . ?
O2 C9 O1 121.2(2) . . ?
O2 C9 C11 123.0(3) . . ?
C5 C11 C6 120.4(2) . . ?
C5 C11 C9 124.7(2) . . ?
C9 C11 C6 114.8(2) . . ?
C19 C13 C17 120.2(3) . . ?
C19 C13 C22 118.4(3) . . ?
C22 C13 C17 121.4(3) . . ?
O4 C15 C7 112.0(2) . . ?
O12 C15 O4 121.1(3) . . ?
O12 C15 C7 126.8(3) . . ?
O1 C17 C13 107.1(2) . . ?
C24 C18 C21 121.9(4) . . ?
C24 C18 C26 118.3(4) . . ?
C26 C18 C21 119.6(3) . . ?
C20 C19 C13 120.5(3) . . ?
C23 C20 C19 120.7(4) . . ?
O4 C21 C18 112.2(3) . . ?
C25 C22 C13 120.6(4) . . ?
C20 C23 C25 119.6(4) . . ?
C18 C24 C28 121.2(4) . . ?
C22 C25 C23 120.3(4) . . ?
C27 C26 C18 121.2(4) . . ?
C29 C27 C26 120.2(5) . . ?
C29 C28 C24 118.9(4) . . ?
C27 C29 C28 120.2(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
O1 C9 C11 C5 6.0(4) . . . . ?
O1 C9 C11 C6 -171.2(2) . . . . ?
O2 C9 C11 C5 -172.5(3) . . . . ?
O2 C9 C11 C6 10.3(4) . . . . ?
N3 C5 C11 C6 -10.5(4) . . . . ?
N3 C5 C11 C9 172.5(2) . . . . ?
C5 N3 C8 C7 12.0(4) . . . . ?
C5 N3 C8 C16 -168.1(3) . . . . ?
C6 C7 C8 N3 5.0(4) . . . . ?
C6 C7 C8 C16 -174.9(3) . . . . ?
C6 C7 C15 O4 -11.2(4) . . . . ?
C6 C7 C15 O12 167.5(3) . . . . ?
C7 C6 C11 C5 24.4(4) . . . . ?
C7 C6 C11 C9 -158.3(2) . . . . ?
C8 N3 C5 C10 170.4(3) . . . . ?
C8 N3 C5 C11 -9.1(4) . . . . ?
C8 C7 C15 O4 172.7(2) . . . . ?
C8 C7 C15 O12 -8.6(5) . . . . ?
C9 O1 C17 C13 175.5(3) . . . . ?
C10 C5 C11 C6 170.1(3) . . . . ?
C10 C5 C11 C9 -6.9(5) . . . . ?
C11 C6 C7 C8 -21.5(3) . . . . ?
C11 C6 C7 C15 162.4(2) . . . . ?
C13 C19 C20 C23 -0.3(5) . . . . ?
C13 C22 C25 C23 -0.4(6) . . . . ?
C14 C6 C7 C8 101.3(3) . . . . ?
C14 C6 C7 C15 -74.7(3) . . . . ?
C14 C6 C11 C5 -98.8(3) . . . . ?
C14 C6 C11 C9 78.5(3) . . . . ?
C15 O4 C21 C18 -80.0(4) . . . . ?
C15 C7 C8 N3 -179.0(2) . . . . ?
C15 C7 C8 C16 1.2(4) . . . . ?
C17 O1 C9 O2 2.8(4) . . . . ?
C17 O1 C9 C11 -175.8(3) . . . . ?
C17 C13 C19 C20 -178.6(3) . . . . ?
C17 C13 C22 C25 179.0(3) . . . . ?
C18 C24 C28 C29 0.2(8) . . . . ?
C18 C26 C27 C29 1.2(8) . . . . ?
C19 C13 C17 O1 117.0(3) . . . . ?
C19 C13 C22 C25 -1.1(5) . . . . ?
C19 C20 C23 C25 -1.3(5) . . . . ?
C20 C23 C25 C22 1.7(6) . . . . ?
C21 O4 C15 C7 177.0(2) . . . . ?
C21 O4 C15 O12 -1.8(5) . . . . ?
C21 C18 C24 C28 176.4(4) . . . . ?
C21 C18 C26 C27 -177.2(4) . . . . ?
C22 C13 C17 O1 -63.2(4) . . . . ?
C22 C13 C19 C20 1.5(4) . . . . ?
C24 C18 C21 O4 114.3(4) . . . . ?
C24 C18 C26 C27 -1.6(6) . . . . ?
C24 C28 C29 C27 -0.7(8) . . . . ?
C26 C18 C21 O4 -70.3(4) . . . . ?
C26 C18 C24 C28 0.9(6) . . . . ?
C26 C27 C29 C28 0.0(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1424344'
_audit_update_record             
;
2015-09-14 deposited with the CCDC.
2016-12-06 downloaded from the CCDC.
;
_audit_creation_date             2014-11-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.25 svn.r3098 for OlexSys, GUI svn.r4951)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H25 N O4, C H2'
_chemical_formula_sum            'C17 H27 N O4'
_chemical_formula_weight         309.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_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                   32.5484(12)
_cell_length_b                   32.5484(12)
_cell_length_c                   8.2649(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7582.8(6)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    2506
_cell_measurement_temperature    110
_cell_measurement_theta_max      72.2230
_cell_measurement_theta_min      4.6810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3024
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7515
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.613
_diffrn_reflns_theta_min         5.436
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  -30.0000 67

#__ type_ start__ end____ width___ exp.time_
  3 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  -90.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega   27.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -130.0000  107.0000 66

#__ type_ start__ end____ width___ exp.time_
  5 omega   39.00  109.00   1.0000    7.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

#__ type_ start__ end____ width___ exp.time_
  6 omega   40.00   98.00   1.0000    7.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

#__ type_ start__ end____ width___ exp.time_
  7 omega   40.00   98.00   1.0000    7.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00   91.00   1.0000    7.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
  9 omega   39.00  109.00   1.0000    7.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 70

#__ type_ start__ end____ width___ exp.time_
 10 omega   91.00  116.00   1.0000    7.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0498141000
_diffrn_orient_matrix_UB_12      0.0440236000
_diffrn_orient_matrix_UB_13      -0.0130948000
_diffrn_orient_matrix_UB_21      0.0212966000
_diffrn_orient_matrix_UB_22      -0.0323403000
_diffrn_orient_matrix_UB_23      -0.0289624000
_diffrn_orient_matrix_UB_31      -0.0069725000
_diffrn_orient_matrix_UB_32      0.0018615000
_diffrn_orient_matrix_UB_33      -0.1837004000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2663
_reflns_number_total             3129
_reflns_odcompleteness_completeness 95.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0690
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1450P)²+6.7720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2017
_refine_ls_wR_factor_ref         0.2154
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00C(H00C)
2.b Secondary CH2 refined with riding coordinates:
 C00D(H00A,H00B), C00E(H00D,H00E), C00H(H00L,H00M), C00K(H00T,H00U), C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 N005(H005)
2.d Idealised Me refined as rotating group:
 C00F(H00F,H00G,H00H), C00G(H00I,H00J,H00K), C00I(H00N,H00O,H00P), C00J(H00Q,
 H00R,H00S), C00L(H00V,H00W,H00X)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O001 O 0.49121(6) 0.95351(6) 0.33998(18) 0.0273(4) Uani 1 1 d . . . . .
O002 O 0.57711(6) 0.94851(6) 0.77317(18) 0.0288(4) Uani 1 1 d . . . . .
O003 O 0.45456(6) 0.89450(6) 0.16019(19) 0.0305(4) Uani 1 1 d . . . . .
O004 O 0.57776(6) 0.88200(6) 0.83581(18) 0.0319(4) Uani 1 1 d . . . . .
N005 N 0.55036(7) 0.84917(7) 0.3286(2) 0.0245(4) Uani 1 1 d . . . . .
H005 H 0.5600 0.8330 0.2701 0.029 Uiso 1 1 calc R . . . .
C006 C 0.57339(8) 0.90621(8) 0.7345(2) 0.0245(5) Uani 1 1 d . . . . .
C007 C 0.48445(7) 0.91375(7) 0.2656(2) 0.0223(5) Uani 1 1 d . . . . .
C008 C 0.51717(7) 0.89887(8) 0.3269(2) 0.0222(5) Uani 1 1 d . . . . .
C009 C 0.52055(7) 0.86276(8) 0.2584(2) 0.0229(5) Uani 1 1 d . . . . .
C00A C 0.56574(8) 0.85995(8) 0.4874(2) 0.0240(5) Uani 1 1 d . . . . .
C00B C 0.56306(7) 0.89582(8) 0.5614(2) 0.0234(5) Uani 1 1 d . . . . .
C00C C 0.55195(8) 0.92786(8) 0.4596(2) 0.0242(5) Uani 1 1 d . . . . .
H00C H 0.5366 0.9413 0.5306 0.029 Uiso 1 1 calc R . . . .
C00D C 0.49381(8) 0.83324(8) 0.1143(2) 0.0247(5) Uani 1 1 d . . . . .
H00A H 0.5128 0.8210 0.0611 0.030 Uiso 1 1 calc R . . . .
H00B H 0.4891 0.8534 0.0353 0.030 Uiso 1 1 calc R . . . .
C00E C 0.58422(9) 0.82925(8) 0.5547(3) 0.0301(5) Uani 1 1 d . . . . .
H00D H 0.5997 0.8425 0.6600 0.036 Uiso 1 1 calc R . . . .
H00E H 0.6088 0.8307 0.4804 0.036 Uiso 1 1 calc R . . . .
C00F C 0.46136(8) 0.97195(9) 0.2865(3) 0.0298(5) Uani 1 1 d . . . . .
H00F H 0.4653 0.9778 0.1697 0.045 Uiso 1 1 calc GR . . . .
H00G H 0.4704 1.0017 0.3433 0.045 Uiso 1 1 calc GR . . . .
H00H H 0.4281 0.9488 0.3102 0.045 Uiso 1 1 calc GR . . . .
C00G C 0.59728(9) 0.96910(8) 0.3882(3) 0.0313(5) Uani 1 1 d . . . . .
H00I H 0.6116 0.9567 0.3123 0.047 Uiso 1 1 calc GR . . . .
H00J H 0.6198 0.9863 0.4756 0.047 Uiso 1 1 calc GR . . . .
H00K H 0.5895 0.9907 0.3310 0.047 Uiso 1 1 calc GR . . . .
C00H C 0.44569(9) 0.79171(8) 0.1632(3) 0.0314(5) Uani 1 1 d . . . . .
H00L H 0.4266 0.8041 0.2149 0.038 Uiso 1 1 calc R . . . .
H00M H 0.4504 0.7719 0.2436 0.038 Uiso 1 1 calc R . . . .
C00I C 0.58461(9) 0.96058(9) 0.9421(3) 0.0330(5) Uani 1 1 d . . . . .
H00N H 0.5892 0.9925 0.9578 0.049 Uiso 1 1 calc GR . . . .
H00O H 0.6128 0.9599 0.9796 0.049 Uiso 1 1 calc GR . . . .
H00P H 0.5569 0.9376 1.0040 0.049 Uiso 1 1 calc GR . . . .
C00J C 0.41849(9) 0.76098(9) 0.0181(3) 0.0352(6) Uani 1 1 d . . . . .
H00Q H 0.4136 0.7804 -0.0617 0.053 Uiso 1 1 calc GR . . . .
H00R H 0.3877 0.7351 0.0542 0.053 Uiso 1 1 calc GR . . . .
H00S H 0.4367 0.7477 -0.0311 0.053 Uiso 1 1 calc GR . . . .
C00K C 0.54623(10) 0.77717(9) 0.5792(3) 0.0359(6) Uani 1 1 d . . . . .
H00T H 0.5299 0.7641 0.4749 0.043 Uiso 1 1 calc R . . . .
H00U H 0.5619 0.7591 0.6113 0.043 Uiso 1 1 calc R . . . .
C00L C 0.50970(12) 0.76993(10) 0.7054(4) 0.0465(7) Uani 1 1 d . . . . .
H00V H 0.4926 0.7862 0.6716 0.070 Uiso 1 1 calc GR . . . .
H00W H 0.5255 0.7830 0.8090 0.070 Uiso 1 1 calc GR . . . .
H00X H 0.4872 0.7359 0.7176 0.070 Uiso 1 1 calc GR . . . .
C1 C 0.3747(3) 0.7103(3) -0.3699(6) 0.143(4) Uani 1 1 d . . . . .
H1A H 0.3719 0.7073 -0.4891 0.172 Uiso 1 1 calc R . . . .
H1B H 0.4035 0.7407 -0.3423 0.172 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C007 1.348(3) . ?
O001 C00F 1.443(3) . ?
O002 C006 1.359(3) . ?
O002 C00I 1.438(3) . ?
O003 C007 1.220(3) . ?
O004 C006 1.206(3) . ?
N005 H005 0.8800 . ?
N005 C009 1.379(3) . ?
N005 C00A 1.386(3) . ?
C006 C00B 1.470(3) . ?
C007 C008 1.463(3) . ?
C008 C009 1.358(3) . ?
C008 C00C 1.518(3) . ?
C009 C00D 1.504(3) . ?
C00A C00B 1.359(3) . ?
C00A C00E 1.507(3) . ?
C00B C00C 1.518(3) . ?
C00C H00C 1.0000 . ?
C00C C00G 1.532(3) . ?
C00D H00A 0.9900 . ?
C00D H00B 0.9900 . ?
C00D C00H 1.525(3) . ?
C00E H00D 0.9900 . ?
C00E H00E 0.9900 . ?
C00E C00K 1.532(4) . ?
C00F H00F 0.9800 . ?
C00F H00G 0.9800 . ?
C00F H00H 0.9800 . ?
C00G H00I 0.9800 . ?
C00G H00J 0.9800 . ?
C00G H00K 0.9800 . ?
C00H H00L 0.9900 . ?
C00H H00M 0.9900 . ?
C00H C00J 1.528(3) . ?
C00I H00N 0.9800 . ?
C00I H00O 0.9800 . ?
C00I H00P 0.9800 . ?
C00J H00Q 0.9800 . ?
C00J H00R 0.9800 . ?
C00J H00S 0.9800 . ?
C00K H00T 0.9900 . ?
C00K H00U 0.9900 . ?
C00K C00L 1.509(4) . ?
C00L H00V 0.9800 . ?
C00L H00W 0.9800 . ?
C00L H00X 0.9800 . ?
C1 C1 1.511(8) 15_554 ?
C1 C1 1.511(8) 14_454 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?

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
C007 O001 C00F 116.05(16) . . ?
C006 O002 C00I 114.97(17) . . ?
C009 N005 H005 118.7 . . ?
C009 N005 C00A 122.67(17) . . ?
C00A N005 H005 118.7 . . ?
O002 C006 C00B 110.87(18) . . ?
O004 C006 O002 121.28(19) . . ?
O004 C006 C00B 127.8(2) . . ?
O001 C007 C008 111.32(17) . . ?
O003 C007 O001 121.63(19) . . ?
O003 C007 C008 127.05(19) . . ?
C007 C008 C00C 118.95(18) . . ?
C009 C008 C007 121.95(18) . . ?
C009 C008 C00C 118.78(18) . . ?
N005 C009 C00D 113.78(18) . . ?
C008 C009 N005 118.44(18) . . ?
C008 C009 C00D 127.73(19) . . ?
N005 C00A C00E 113.27(18) . . ?
C00B C00A N005 118.28(19) . . ?
C00B C00A C00E 128.45(19) . . ?
C006 C00B C00C 119.16(18) . . ?
C00A C00B C006 122.02(19) . . ?
C00A C00B C00C 118.71(18) . . ?
C008 C00C H00C 108.4 . . ?
C008 C00C C00G 111.02(17) . . ?
C00B C00C C008 109.45(17) . . ?
C00B C00C H00C 108.4 . . ?
C00B C00C C00G 111.08(17) . . ?
C00G C00C H00C 108.4 . . ?
C009 C00D H00A 109.3 . . ?
C009 C00D H00B 109.3 . . ?
C009 C00D C00H 111.49(17) . . ?
H00A C00D H00B 108.0 . . ?
C00H C00D H00A 109.3 . . ?
C00H C00D H00B 109.3 . . ?
C00A C00E H00D 108.7 . . ?
C00A C00E H00E 108.7 . . ?
C00A C00E C00K 114.4(2) . . ?
H00D C00E H00E 107.6 . . ?
C00K C00E H00D 108.7 . . ?
C00K C00E H00E 108.7 . . ?
O001 C00F H00F 109.5 . . ?
O001 C00F H00G 109.5 . . ?
O001 C00F H00H 109.5 . . ?
H00F C00F H00G 109.5 . . ?
H00F C00F H00H 109.5 . . ?
H00G C00F H00H 109.5 . . ?
C00C C00G H00I 109.5 . . ?
C00C C00G H00J 109.5 . . ?
C00C C00G H00K 109.5 . . ?
H00I C00G H00J 109.5 . . ?
H00I C00G H00K 109.5 . . ?
H00J C00G H00K 109.5 . . ?
C00D C00H H00L 109.2 . . ?
C00D C00H H00M 109.2 . . ?
C00D C00H C00J 111.99(19) . . ?
H00L C00H H00M 107.9 . . ?
C00J C00H H00L 109.2 . . ?
C00J C00H H00M 109.2 . . ?
O002 C00I H00N 109.5 . . ?
O002 C00I H00O 109.5 . . ?
O002 C00I H00P 109.5 . . ?
H00N C00I H00O 109.5 . . ?
H00N C00I H00P 109.5 . . ?
H00O C00I H00P 109.5 . . ?
C00H C00J H00Q 109.5 . . ?
C00H C00J H00R 109.5 . . ?
C00H C00J H00S 109.5 . . ?
H00Q C00J H00R 109.5 . . ?
H00Q C00J H00S 109.5 . . ?
H00R C00J H00S 109.5 . . ?
C00E C00K H00T 108.8 . . ?
C00E C00K H00U 108.8 . . ?
H00T C00K H00U 107.7 . . ?
C00L C00K C00E 113.6(2) . . ?
C00L C00K H00T 108.8 . . ?
C00L C00K H00U 108.8 . . ?
C00K C00L H00V 109.5 . . ?
C00K C00L H00W 109.5 . . ?
C00K C00L H00X 109.5 . . ?
H00V C00L H00W 109.5 . . ?
H00V C00L H00X 109.5 . . ?
H00W C00L H00X 109.5 . . ?
C1 C1 C1 105.1(4) 14_454 15_554 ?
C1 C1 H1A 110.7 14_454 . ?
C1 C1 H1A 110.7 15_554 . ?
C1 C1 H1B 110.7 15_554 . ?
C1 C1 H1B 110.7 14_454 . ?
H1A C1 H1B 108.8 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2014-11-26
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_luo26
_database_code_depnum_ccdc_archive 'CCDC 1424354'
_audit_update_record             
;
2015-09-14 deposited with the CCDC.
2016-12-06 downloaded from the CCDC.
;
_audit_creation_date             2013-05-02
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H17 N O4'
_chemical_formula_sum            'C12 H17 N O4'
_chemical_formula_weight         239.26
_chemical_melting_point          ?
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'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.462(7)
_cell_length_b                   7.524(7)
_cell_length_c                   11.643(11)
_cell_angle_alpha                98.794(13)
_cell_angle_beta                 90.593(14)
_cell_angle_gamma                103.259(13)
_cell_volume                     628.1(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1368
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.91
_cell_measurement_theta_min      2.81
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_av_unetI/netI     0.1077
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6334
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         1.772
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1230
_reflns_number_total             2494
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL-2012, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2494
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1632
_refine_ls_R_factor_gt           0.0822
_refine_ls_restrained_S_all      0.979
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1369P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2039
_refine_ls_wR_factor_ref         0.2523
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C),
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0155(4) 0.2977(4) 0.0737(2) 0.0590(9) Uani 1 1 d . . . . .
O2 O 0.8004(4) 0.2113(4) -0.0716(2) 0.0540(8) Uani 1 1 d . . . . .
O3 O 0.9133(4) 0.6910(5) 0.4186(3) 0.0783(11) Uani 1 1 d . . . . .
O4 O 0.6432(4) 0.7586(4) 0.4558(3) 0.0690(10) Uani 1 1 d . . . . .
N1 N 0.4122(4) 0.3563(4) 0.1660(3) 0.0432(8) Uani 1 1 d . . . . .
H1 H 0.2955 0.3116 0.1544 0.052 Uiso 1 1 calc R U . . .
C1 C 0.5293(5) 0.2987(5) 0.0830(3) 0.0371(9) Uani 1 1 d . . . . .
C2 C 0.7109(5) 0.3230(5) 0.1165(3) 0.0365(9) Uani 1 1 d . . . . .
C3 C 0.7737(5) 0.3901(5) 0.2431(3) 0.0423(9) Uani 1 1 d . . . . .
H3 H 0.9011 0.4632 0.2461 0.051 Uiso 1 1 calc R U . . .
C4 C 0.6548(5) 0.5139(5) 0.3017(3) 0.0405(9) Uani 1 1 d . . . . .
C5 C 0.4753(5) 0.4826(5) 0.2665(3) 0.0416(9) Uani 1 1 d . . . . .
C6 C 0.4328(5) 0.2163(6) -0.0325(3) 0.0483(10) Uani 1 1 d . . . . .
H6A H 0.3063 0.1602 -0.0216 0.072 Uiso 1 1 calc R U . . .
H6B H 0.4917 0.1241 -0.0708 0.072 Uiso 1 1 calc R U . . .
H6C H 0.4384 0.3115 -0.0795 0.072 Uiso 1 1 calc R U . . .
C7 C 0.7696(7) 0.2261(7) 0.3092(4) 0.0682(14) Uani 1 1 d . . . . .
H7A H 0.6460 0.1519 0.3065 0.102 Uiso 1 1 calc R U . . .
H7B H 0.8112 0.2725 0.3888 0.102 Uiso 1 1 calc R U . . .
H7C H 0.8492 0.1521 0.2735 0.102 Uiso 1 1 calc R U . . .
C8 C 0.3252(6) 0.5702(7) 0.3197(4) 0.0618(13) Uani 1 1 d . . . . .
H8A H 0.3394 0.6912 0.2989 0.093 Uiso 1 1 calc R U . . .
H8B H 0.3345 0.5802 0.4028 0.093 Uiso 1 1 calc R U . . .
H8C H 0.2067 0.4948 0.2909 0.093 Uiso 1 1 calc R U . . .
C9 C 0.8560(5) 0.2791(5) 0.0402(3) 0.0397(9) Uani 1 1 d . . . . .
C10 C 0.9397(6) 0.1583(7) -0.1471(4) 0.0623(13) Uani 1 1 d . . . . .
H10A H 0.8892 0.1220 -0.2256 0.094 Uiso 1 1 calc R U . . .
H10B H 0.9779 0.0566 -0.1218 0.094 Uiso 1 1 calc R U . . .
H10C H 1.0440 0.2613 -0.1438 0.094 Uiso 1 1 calc R U . . .
C11 C 0.7504(5) 0.6592(6) 0.3960(3) 0.0480(10) Uani 1 1 d . . . . .
C12 C 0.7333(7) 0.9021(7) 0.5483(4) 0.0773(16) Uani 1 1 d . . . . .
H12A H 0.8190 0.9955 0.5162 0.116 Uiso 1 1 calc R U . . .
H12B H 0.7981 0.8502 0.6012 0.116 Uiso 1 1 calc R U . . .
H12C H 0.6428 0.9563 0.5890 0.116 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.219(4) . ?
O2 C9 1.347(4) . ?
O2 C10 1.454(4) . ?
O3 C11 1.202(5) . ?
O4 C11 1.346(4) . ?
O4 C12 1.440(5) . ?
N1 H1 0.8600 . ?
N1 C1 1.395(4) . ?
N1 C5 1.392(4) . ?
C1 C2 1.369(5) . ?
C1 C6 1.495(5) . ?
C2 C3 1.515(5) . ?
C2 C9 1.472(5) . ?
C3 H3 0.9800 . ?
C3 C4 1.523(4) . ?
C3 C7 1.546(6) . ?
C4 C5 1.353(5) . ?
C4 C11 1.472(5) . ?
C5 C8 1.517(5) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O2 C10 116.1(3) . . ?
C11 O4 C12 116.6(3) . . ?
C1 N1 H1 118.4 . . ?
C5 N1 H1 118.4 . . ?
C5 N1 C1 123.2(3) . . ?
N1 C1 C6 113.1(3) . . ?
C2 C1 N1 117.7(3) . . ?
C2 C1 C6 129.2(3) . . ?
C1 C2 C3 119.8(3) . . ?
C1 C2 C9 125.5(3) . . ?
C9 C2 C3 114.6(3) . . ?
C2 C3 H3 108.2 . . ?
C2 C3 C4 110.5(3) . . ?
C2 C3 C7 111.3(3) . . ?
C4 C3 H3 108.2 . . ?
C4 C3 C7 110.3(3) . . ?
C7 C3 H3 108.2 . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 C11 125.7(3) . . ?
C11 C4 C3 114.8(3) . . ?
N1 C5 C8 112.2(3) . . ?
C4 C5 N1 118.4(3) . . ?
C4 C5 C8 129.3(3) . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 O2 121.0(3) . . ?
O1 C9 C2 123.7(3) . . ?
O2 C9 C2 115.3(3) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 O4 121.1(4) . . ?
O3 C11 C4 123.4(3) . . ?
O4 C11 C4 115.4(3) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.972
_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.
;
_shelxl_version_number           2013-2
