# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_madiha1cult_cpd1
_database_code_depnum_ccdc_archive 'CCDC 1569108'
_audit_update_record             
;
2017-08-15 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2017-08-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            11-Azaart
_chemical_name_systematic        11-azaartemisinin
_chemical_formula_moiety         'C15 H23 N O4'
_chemical_formula_sum            'C15 H23 N O4'
_chemical_formula_weight         281.34
_chemical_absolute_configuration ad
_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           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   11.71759(15)
_cell_length_b                   11.71759(15)
_cell_length_c                   9.48728(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1128.10(3)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    4018
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.9010
_cell_measurement_theta_min      6.3710
_shelx_estimated_absorpt_T_max   0.917
_shelx_estimated_absorpt_T_min   0.898
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless

_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5621
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.285
_diffrn_reflns_theta_min         4.357
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   36.00   62.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega   77.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   26.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000   60.0000 51

#__ type_ start__ end____ width___ exp.time_
  4 omega  123.00  170.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000  -60.0000 47

#__ type_ start__ end____ width___ exp.time_
  5 omega  127.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   77.0000 -120.0000 50

#__ type_ start__ end____ width___ exp.time_
  6 omega  119.00  174.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   77.0000 -150.0000 55

#__ type_ start__ end____ width___ exp.time_
  7 omega   82.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   61.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega   83.00  118.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   45.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
  9 omega   85.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   45.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   77.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   80.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   61.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   80.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   61.0000  -90.0000 46

#__ type_ start__ end____ width___ exp.time_
 13 omega   78.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega  102.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  111.0000   30.0000 75

#__ type_ start__ end____ width___ exp.time_
 15 omega   33.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000 -120.0000 54

#__ type_ start__ end____ width___ exp.time_
 16 omega   64.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9453 -125.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
 17 omega   23.00   54.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9453 -125.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
 18 omega  -43.00  -12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  -57.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
 19 omega  -75.00  -48.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  -57.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 20 omega -111.00   33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453    0.0000 -180.0000 144

#__ type_ start__ end____ width___ exp.time_
 21 omega -108.00  -83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453 -133.0000  124.0000 25

#__ type_ start__ end____ width___ exp.time_
 22 omega -122.00  -89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  -89.0000  157.0000 33
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1415895000
_diffrn_orient_matrix_UB_12      -0.1119422000
_diffrn_orient_matrix_UB_13      -0.0292878000
_diffrn_orient_matrix_UB_21      0.0549017000
_diffrn_orient_matrix_UB_22      -0.0798797000
_diffrn_orient_matrix_UB_23      -0.0732449000
_diffrn_orient_matrix_UB_31      -0.0004273000
_diffrn_orient_matrix_UB_32      -0.0640041000
_diffrn_orient_matrix_UB_33      0.1418938000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.968
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                2604
_reflns_number_total             2647
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 1256 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2647
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0238
_refine_ls_restrained_S_all      1.016
_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)+(0.0299P)²+0.1784P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0579
_refine_ls_wR_factor_ref         0.0582
_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:
 C2(H2), C6(H6), C9(H9), C11(H11A), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N11(H11)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_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 0.16960(13) 0.42125(12) 0.66077(14) 0.0211(3) Uani 1 1 d . . . . .
O2 O 0.03484(12) 0.32083(12) 0.69935(14) 0.0218(3) Uani 1 1 d . . . . .
O3 O 0.06650(12) 0.14274(12) 0.68619(12) 0.0185(3) Uani 1 1 d . . . . .
O10 O 0.02297(13) 0.24505(13) 0.23629(14) 0.0261(3) Uani 1 1 d . . . . .
N11 N 0.07470(14) 0.19339(14) 0.44563(15) 0.0176(3) Uani 1 1 d . . . . .
H11 H 0.0068 0.1135 0.4350 0.021 Uiso 1 1 calc R . . . .
C1 C 0.24341(17) 0.36109(17) 0.60435(18) 0.0171(4) Uani 1 1 d . . . . .
C2 C 0.15298(17) 0.21442(17) 0.57172(18) 0.0168(4) Uani 1 1 d . . . . .
H2 H 0.2106 0.1755 0.5542 0.020 Uiso 1 1 calc R . . . .
C3 C 0.04295(19) 0.22423(18) 0.78127(19) 0.0214(4) Uani 1 1 d . . . . .
C4 C 0.1505(2) 0.2843(2) 0.8945(2) 0.0271(4) Uani 1 1 d . . . . .
H4A H 0.1642 0.3722 0.9202 0.032 Uiso 1 1 calc R . . . .
H4B H 0.1189 0.2283 0.9798 0.032 Uiso 1 1 calc R . . . .
C5 C 0.2829(2) 0.2993(2) 0.85055(19) 0.0261(4) Uani 1 1 d . . . . .
H5A H 0.2706 0.2102 0.8361 0.031 Uiso 1 1 calc R . . . .
H5B H 0.3456 0.3403 0.9296 0.031 Uiso 1 1 calc R . . . .
C6 C 0.45464(19) 0.3561(2) 0.6584(2) 0.0263(4) Uani 1 1 d . . . . .
H6 H 0.4138 0.2603 0.6354 0.032 Uiso 1 1 calc R . . . .
C7 C 0.51255(19) 0.43458(19) 0.5235(2) 0.0254(4) Uani 1 1 d . . . . .
H7A H 0.5776 0.4126 0.4846 0.031 Uiso 1 1 calc R . . . .
H7B H 0.5599 0.5297 0.5465 0.031 Uiso 1 1 calc R . . . .
C8 C 0.40906(18) 0.40802(18) 0.4114(2) 0.0219(4) Uani 1 1 d . . . . .
H8A H 0.3656 0.3144 0.3823 0.026 Uiso 1 1 calc R . . . .
H8B H 0.4519 0.4632 0.3274 0.026 Uiso 1 1 calc R . . . .
C9 C 0.19809(18) 0.42334(17) 0.36574(19) 0.0194(4) Uani 1 1 d . . . . .
H9 H 0.1529 0.4675 0.4102 0.023 Uiso 1 1 calc R . . . .
C10 C 0.09219(17) 0.28021(17) 0.34225(18) 0.0185(4) Uani 1 1 d . . . . .
C11 C 0.34608(18) 0.38083(18) 0.7172(2) 0.0221(4) Uani 1 1 d . . . . .
H11A H 0.3903 0.4756 0.7459 0.026 Uiso 1 1 calc R . . . .
C12 C 0.30601(17) 0.43951(17) 0.46987(18) 0.0176(4) Uani 1 1 d . . . . .
H12 H 0.3548 0.5345 0.4978 0.021 Uiso 1 1 calc R . . . .
C13 C -0.0936(2) 0.1408(2) 0.8427(2) 0.0268(4) Uani 1 1 d . . . . .
H13A H -0.1597 0.1246 0.7703 0.040 Uiso 1 1 calc GR . . . .
H13B H -0.1052 0.1873 0.9224 0.040 Uiso 1 1 calc GR . . . .
H13C H -0.1044 0.0566 0.8751 0.040 Uiso 1 1 calc GR . . . .
C14 C 0.5642(2) 0.3910(3) 0.7664(3) 0.0428(6) Uani 1 1 d . . . . .
H14A H 0.6345 0.3807 0.7234 0.064 Uiso 1 1 calc GR . . . .
H14B H 0.5283 0.3321 0.8479 0.064 Uiso 1 1 calc GR . . . .
H14C H 0.5998 0.4824 0.7971 0.064 Uiso 1 1 calc GR . . . .
C15 C 0.2523(2) 0.4928(2) 0.2248(2) 0.0281(4) Uani 1 1 d . . . . .
H15A H 0.2940 0.4501 0.1746 0.042 Uiso 1 1 calc GR . . . .
H15B H 0.3177 0.5855 0.2417 0.042 Uiso 1 1 calc GR . . . .
H15C H 0.1801 0.4874 0.1677 0.042 Uiso 1 1 calc GR . . . .


_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 O2 1.4676(18) . ?
O1 C1 1.463(2) . ?
O2 C3 1.415(2) . ?
O3 C2 1.435(2) . ?
O3 C3 1.437(2) . ?
O10 C10 1.226(2) . ?
N11 C2 1.452(2) . ?
N11 C10 1.353(2) . ?
C1 C2 1.533(2) . ?
C1 C11 1.539(2) . ?
C1 C12 1.528(2) . ?
C3 C4 1.533(3) . ?
C3 C13 1.514(3) . ?
C4 C5 1.530(3) . ?
C5 C11 1.534(3) . ?
C6 C7 1.523(3) . ?
C6 C11 1.543(3) . ?
C6 C14 1.529(3) . ?
C7 C8 1.524(3) . ?
C8 C12 1.532(2) . ?
C9 C10 1.524(2) . ?
C9 C12 1.540(2) . ?
C9 C15 1.529(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 O2 111.29(12) . . ?
C3 O2 O1 107.62(13) . . ?
C2 O3 C3 113.58(13) . . ?
C10 N11 C2 128.65(14) . . ?
O1 C1 C2 111.73(14) . . ?
O1 C1 C11 106.19(14) . . ?
O1 C1 C12 103.73(13) . . ?
C2 C1 C11 111.04(14) . . ?
C12 C1 C2 111.12(14) . . ?
C12 C1 C11 112.73(14) . . ?
O3 C2 N11 108.83(14) . . ?
O3 C2 C1 113.15(14) . . ?
N11 C2 C1 112.36(14) . . ?
O2 C3 O3 107.38(13) . . ?
O2 C3 C4 112.70(15) . . ?
O2 C3 C13 104.83(15) . . ?
O3 C3 C4 111.00(16) . . ?
O3 C3 C13 107.73(15) . . ?
C13 C3 C4 112.81(16) . . ?
C5 C4 C3 114.54(16) . . ?
C4 C5 C11 116.24(16) . . ?
C7 C6 C11 110.51(16) . . ?
C7 C6 C14 109.91(17) . . ?
C14 C6 C11 111.59(18) . . ?
C6 C7 C8 113.24(16) . . ?
C7 C8 C12 109.91(15) . . ?
C10 C9 C12 113.34(14) . . ?
C10 C9 C15 110.55(15) . . ?
C15 C9 C12 113.49(15) . . ?
O10 C10 N11 121.04(16) . . ?
O10 C10 C9 121.84(16) . . ?
N11 C10 C9 117.09(15) . . ?
C1 C11 C6 112.08(15) . . ?
C5 C11 C1 112.49(15) . . ?
C5 C11 C6 111.56(16) . . ?
C1 C12 C8 110.89(14) . . ?
C1 C12 C9 110.11(14) . . ?
C8 C12 C9 115.82(14) . . ?

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 O2 C3 O3 -77.21(16) . . . . ?
O1 O2 C3 C4 45.34(18) . . . . ?
O1 O2 C3 C13 168.39(13) . . . . ?
O1 C1 C2 O3 -49.49(19) . . . . ?
O1 C1 C2 N11 74.26(18) . . . . ?
O1 C1 C11 C5 68.45(18) . . . . ?
O1 C1 C11 C6 -164.88(14) . . . . ?
O1 C1 C12 C8 168.93(14) . . . . ?
O1 C1 C12 C9 -61.56(16) . . . . ?
O2 O1 C1 C2 12.13(18) . . . . ?
O2 O1 C1 C11 -109.08(14) . . . . ?
O2 O1 C1 C12 131.91(13) . . . . ?
O2 C3 C4 C5 -94.7(2) . . . . ?
O3 C3 C4 C5 25.8(2) . . . . ?
C1 O1 O2 C3 48.65(16) . . . . ?
C2 O3 C3 O2 37.59(19) . . . . ?
C2 O3 C3 C4 -86.00(17) . . . . ?
C2 O3 C3 C13 150.03(15) . . . . ?
C2 N11 C10 O10 174.58(17) . . . . ?
C2 N11 C10 C9 -7.3(3) . . . . ?
C2 C1 C11 C5 -53.2(2) . . . . ?
C2 C1 C11 C6 73.48(19) . . . . ?
C2 C1 C12 C8 -70.89(18) . . . . ?
C2 C1 C12 C9 58.62(17) . . . . ?
C3 O3 C2 N11 -102.38(16) . . . . ?
C3 O3 C2 C1 23.28(19) . . . . ?
C3 C4 C5 C11 56.9(2) . . . . ?
C4 C5 C11 C1 -36.2(2) . . . . ?
C4 C5 C11 C6 -163.17(16) . . . . ?
C6 C7 C8 C12 57.8(2) . . . . ?
C7 C6 C11 C1 50.9(2) . . . . ?
C7 C6 C11 C5 178.12(15) . . . . ?
C7 C8 C12 C1 -56.27(19) . . . . ?
C7 C8 C12 C9 177.32(15) . . . . ?
C10 N11 C2 O3 142.19(17) . . . . ?
C10 N11 C2 C1 16.1(2) . . . . ?
C10 C9 C12 C1 -49.69(19) . . . . ?
C10 C9 C12 C8 77.11(19) . . . . ?
C11 C1 C2 O3 68.86(18) . . . . ?
C11 C1 C2 N11 -167.39(14) . . . . ?
C11 C1 C12 C8 54.50(18) . . . . ?
C11 C1 C12 C9 -175.99(14) . . . . ?
C11 C6 C7 C8 -55.0(2) . . . . ?
C12 C1 C2 O3 -164.82(14) . . . . ?
C12 C1 C2 N11 -41.07(18) . . . . ?
C12 C1 C11 C5 -178.62(15) . . . . ?
C12 C1 C11 C6 -51.95(19) . . . . ?
C12 C9 C10 O10 -157.90(16) . . . . ?
C12 C9 C10 N11 24.0(2) . . . . ?
C13 C3 C4 C5 146.85(17) . . . . ?
C14 C6 C7 C8 -178.56(18) . . . . ?
C14 C6 C11 C1 173.56(16) . . . . ?
C14 C6 C11 C5 -59.3(2) . . . . ?
C15 C9 C10 O10 -29.2(2) . . . . ?
C15 C9 C10 N11 152.73(16) . . . . ?
C15 C9 C12 C1 -176.87(15) . . . . ?
C15 C9 C12 C8 -50.1(2) . . . . ?

_olex2_date_sample_data_collection 2016-03-17
_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_cpd2_madiha36cult
_database_code_depnum_ccdc_archive 'CCDC 1569109'
_audit_update_record             
;
2017-08-15 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2017-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            11-Aza:Ben
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H23 N O4, C7 H6 O2'
_chemical_formula_sum            'C22 H29 N O6'
_chemical_formula_weight         403.46
_chemical_absolute_configuration ad
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.64312(19)
_cell_length_b                   9.3622(2)
_cell_length_c                   22.8165(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.9437(18)
_cell_angle_gamma                90
_cell_volume                     2059.60(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5119
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.3250
_cell_measurement_theta_min      4.5700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11649
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.499
_diffrn_reflns_theta_min         3.875
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     48.00 106.00   1.00    3.00    --  110.57-102.00 119.00   58
  2  ω     11.00 117.00   1.00    1.00    --   40.57  77.00-180.00  106
  3  ω    -67.00  36.00   1.00    1.00    --  -40.57  37.00-120.00  103
  4  ω    -65.00  36.00   1.00    1.00    --  -40.57  37.00 150.00  101
  5  ω     42.00 128.00   1.00    3.00    --  110.57 -30.00  30.00   86
  6  ω     85.00 172.00   1.00    3.00    --  110.57  41.00   7.00   87
  7  ω     80.00 170.00   1.00    3.00    --  110.57  61.00-150.00   90
  8  ω     83.00 178.00   1.00    3.00    --  110.57  77.00  30.00   95
  9  ω     81.00 146.00   1.00    3.00    --  110.57  77.00 120.00   65
 10  ω     73.00 131.00   1.00    3.00    --  110.57 178.00 -90.00   58
 11  ω     26.00 106.00   1.00    3.00    --  110.57 -94.00   0.00   80
 12  ω     35.00 115.00   1.00    3.00    --  110.57-111.00-120.00   80
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0430966000
_diffrn_orient_matrix_UB_12      0.1554552000
_diffrn_orient_matrix_UB_13      -0.0128475000
_diffrn_orient_matrix_UB_21      -0.1368507000
_diffrn_orient_matrix_UB_22      -0.0242633000
_diffrn_orient_matrix_UB_23      0.0325116000
_diffrn_orient_matrix_UB_31      0.0704463000
_diffrn_orient_matrix_UB_32      0.0481925000
_diffrn_orient_matrix_UB_33      0.0577464000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.851
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                6668
_reflns_number_total             7317
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 2798 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     545
_refine_ls_number_reflns         7317
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0348
_refine_ls_restrained_S_all      1.004
_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)+(0.0360P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0818
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6), C9(H9), C11(H11A), C12(H12), C2A(H2A), C6A(H6A), C9A(H9A),
 C11A(H11C), C12A(H12A)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C4A(H4AA,H4AB), C5A(H5AA,
 H5AB), C7A(H7AA,H7AB), C8A(H8AA,H8AB)
2.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C22A(H22A), C23A(H23A),
 C24A(H24A), C25A(H25A), C26A(H26A)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C13A(H13D,H13E,
 H13F), C14A(H14D,H14E,H14F), C15A(H15D,H15E,H15F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.4500(2) 0.5659(2) 0.41252(8) 0.0216(4) Uani 1 1 d . . . . .
O2 O 0.59596(19) 0.5856(2) 0.43041(8) 0.0227(4) Uani 1 1 d . . . . .
O3 O 0.64515(19) 0.3462(2) 0.44147(8) 0.0205(4) Uani 1 1 d . . . . .
O10 O 0.4043(2) 0.4837(2) 0.60087(8) 0.0222(4) Uani 1 1 d . . . . .
N11 N 0.5037(2) 0.3900(2) 0.52144(9) 0.0194(5) Uani 1 1 d . . . . .
H11 H 0.576(4) 0.365(4) 0.5450(15) 0.028(9) Uiso 1 1 d . . . . .
C1 C 0.4034(3) 0.4190(3) 0.42145(11) 0.0178(5) Uani 1 1 d . . . . .
C2 C 0.5065(3) 0.3392(3) 0.46098(11) 0.0184(5) Uani 1 1 d . . . . .
H2 H 0.4786 0.2364 0.4611 0.022 Uiso 1 1 calc R . . . .
C3 C 0.6732(3) 0.4707(3) 0.40715(12) 0.0226(6) Uani 1 1 d . . . . .
C4 C 0.6376(3) 0.4447(3) 0.34208(12) 0.0255(6) Uani 1 1 d . . . . .
H4A H 0.6018 0.5346 0.3247 0.031 Uiso 1 1 calc R . . . .
H4B H 0.7237 0.4194 0.3214 0.031 Uiso 1 1 calc R . . . .
C5 C 0.5306(3) 0.3265(3) 0.33155(11) 0.0225(6) Uani 1 1 d . . . . .
H5A H 0.5701 0.2355 0.3462 0.027 Uiso 1 1 calc R . . . .
H5B H 0.5154 0.3162 0.2887 0.027 Uiso 1 1 calc R . . . .
C6 C 0.3061(3) 0.2082(3) 0.36185(12) 0.0206(5) Uani 1 1 d . . . . .
H6 H 0.3640 0.1355 0.3831 0.025 Uiso 1 1 calc R . . . .
C7 C 0.1700(3) 0.2246(3) 0.39448(13) 0.0251(6) Uani 1 1 d . . . . .
H7A H 0.1065 0.2865 0.3713 0.030 Uiso 1 1 calc R . . . .
H7B H 0.1256 0.1297 0.3982 0.030 Uiso 1 1 calc R . . . .
C8 C 0.1908(3) 0.2889(3) 0.45548(12) 0.0224(6) Uani 1 1 d . . . . .
H8A H 0.2479 0.2235 0.4800 0.027 Uiso 1 1 calc R . . . .
H8B H 0.0997 0.3003 0.4743 0.027 Uiso 1 1 calc R . . . .
C9 C 0.2807(3) 0.5145(3) 0.51004(12) 0.0207(5) Uani 1 1 d . . . . .
H9 H 0.3060 0.6149 0.4997 0.025 Uiso 1 1 calc R . . . .
C10 C 0.3997(3) 0.4585(3) 0.54707(12) 0.0188(5) Uani 1 1 d . . . . .
C11 C 0.3887(3) 0.3493(3) 0.36025(11) 0.0193(5) Uani 1 1 d . . . . .
H11A H 0.3350 0.4172 0.3348 0.023 Uiso 1 1 calc R . . . .
C12 C 0.2629(3) 0.4350(3) 0.45151(11) 0.0189(5) Uani 1 1 d . . . . .
H12 H 0.2035 0.4965 0.4255 0.023 Uiso 1 1 calc R . . . .
C13 C 0.8232(3) 0.5103(4) 0.41866(14) 0.0319(7) Uani 1 1 d . . . . .
H13A H 0.8365 0.5340 0.4602 0.048 Uiso 1 1 calc GR . . . .
H13B H 0.8475 0.5930 0.3946 0.048 Uiso 1 1 calc GR . . . .
H13C H 0.8828 0.4294 0.4086 0.048 Uiso 1 1 calc GR . . . .
C14 C 0.2766(3) 0.1524(3) 0.29962(13) 0.0277(6) Uani 1 1 d . . . . .
H14A H 0.2279 0.2261 0.2767 0.042 Uiso 1 1 calc GR . . . .
H14B H 0.2187 0.0666 0.3016 0.042 Uiso 1 1 calc GR . . . .
H14C H 0.3643 0.1290 0.2808 0.042 Uiso 1 1 calc GR . . . .
C15 C 0.1478(3) 0.5250(4) 0.54545(13) 0.0305(7) Uani 1 1 d . . . . .
H15A H 0.1240 0.4305 0.5608 0.046 Uiso 1 1 calc GR . . . .
H15B H 0.0720 0.5598 0.5201 0.046 Uiso 1 1 calc GR . . . .
H15C H 0.1623 0.5915 0.5782 0.046 Uiso 1 1 calc GR . . . .
O20 O 0.7260(2) 0.3334(2) 0.60924(8) 0.0255(4) Uani 1 1 d . . . . .
O21 O 0.5527(2) 0.3371(2) 0.67374(8) 0.0250(4) Uani 1 1 d . . . . .
H21 H 0.510(4) 0.391(5) 0.6478(19) 0.046(12) Uiso 1 1 d . . . . .
C20 C 0.6760(3) 0.2960(3) 0.65556(12) 0.0217(6) Uani 1 1 d . . . . .
C21 C 0.7481(3) 0.1984(3) 0.69780(12) 0.0220(6) Uani 1 1 d . . . . .
C22 C 0.8781(3) 0.1448(3) 0.68387(12) 0.0246(6) Uani 1 1 d . . . . .
H22 H 0.9217 0.1743 0.6488 0.030 Uiso 1 1 calc R . . . .
C23 C 0.9438(3) 0.0489(3) 0.72100(13) 0.0295(7) Uani 1 1 d . . . . .
H23 H 1.0324 0.0123 0.7113 0.035 Uiso 1 1 calc R . . . .
C24 C 0.8811(3) 0.0055(4) 0.77245(14) 0.0314(7) Uani 1 1 d . . . . .
H24 H 0.9263 -0.0609 0.7977 0.038 Uiso 1 1 calc R . . . .
C25 C 0.7519(3) 0.0598(4) 0.78674(13) 0.0311(7) Uani 1 1 d . . . . .
H25 H 0.7088 0.0306 0.8219 0.037 Uiso 1 1 calc R . . . .
C26 C 0.6856(3) 0.1567(3) 0.74973(13) 0.0256(6) Uani 1 1 d . . . . .
H26 H 0.5978 0.1946 0.7598 0.031 Uiso 1 1 calc R . . . .
O1A O 0.34036(19) 0.3676(2) -0.06387(8) 0.0181(4) Uani 1 1 d . . . . .
O2A O 0.29829(19) 0.3436(2) -0.00298(8) 0.0190(4) Uani 1 1 d . . . . .
O3A O 0.30016(18) 0.5804(2) 0.02397(8) 0.0186(4) Uani 1 1 d . . . . .
O10A O 0.75705(18) 0.4566(2) 0.01828(8) 0.0207(4) Uani 1 1 d . . . . .
N11A N 0.5383(2) 0.5408(2) 0.01496(10) 0.0177(5) Uani 1 1 d . . . . .
H11B H 0.555(4) 0.570(4) 0.0514(16) 0.030(9) Uiso 1 1 d . . . . .
C1A C 0.3862(3) 0.5137(3) -0.07374(11) 0.0167(5) Uani 1 1 d . . . . .
C2A C 0.4122(2) 0.5903(3) -0.01520(11) 0.0165(5) Uani 1 1 d . . . . .
H2A H 0.4255 0.6939 -0.0242 0.020 Uiso 1 1 calc R . . . .
C3A C 0.2122(3) 0.4588(3) 0.01320(12) 0.0195(5) Uani 1 1 d . . . . .
C4A C 0.1010(3) 0.4925(3) -0.03369(12) 0.0225(6) Uani 1 1 d . . . . .
H4AA H 0.0823 0.4049 -0.0568 0.027 Uiso 1 1 calc R . . . .
H4AB H 0.0141 0.5188 -0.0138 0.027 Uiso 1 1 calc R . . . .
C5A C 0.1392(3) 0.6123(3) -0.07567(12) 0.0226(6) Uani 1 1 d . . . . .
H5AA H 0.1496 0.7017 -0.0528 0.027 Uiso 1 1 calc R . . . .
H5AB H 0.0611 0.6262 -0.1038 0.027 Uiso 1 1 calc R . . . .
C6A C 0.3226(3) 0.7295(3) -0.13839(12) 0.0221(6) Uani 1 1 d . . . . .
H6A H 0.3361 0.8011 -0.1063 0.027 Uiso 1 1 calc R . . . .
C7A C 0.4610(3) 0.7109(3) -0.16917(12) 0.0235(6) Uani 1 1 d . . . . .
H7AA H 0.4466 0.6509 -0.2045 0.028 Uiso 1 1 calc R . . . .
H7AB H 0.4946 0.8055 -0.1821 0.028 Uiso 1 1 calc R . . . .
C8A C 0.5713(3) 0.6420(3) -0.12976(12) 0.0216(6) Uani 1 1 d . . . . .
H8AA H 0.5918 0.7053 -0.0960 0.026 Uiso 1 1 calc R . . . .
H8AB H 0.6578 0.6293 -0.1519 0.026 Uiso 1 1 calc R . . . .
C9A C 0.6276(3) 0.4138(3) -0.07081(11) 0.0179(5) Uani 1 1 d . . . . .
H9A H 0.5876 0.3162 -0.0656 0.021 Uiso 1 1 calc R . . . .
C10A C 0.6465(3) 0.4751(3) -0.00936(11) 0.0162(5) Uani 1 1 d . . . . .
C11A C 0.2726(3) 0.5888(3) -0.11069(11) 0.0189(5) Uani 1 1 d . . . . .
H11C H 0.2480 0.5230 -0.1438 0.023 Uiso 1 1 calc R . . . .
C12A C 0.5213(3) 0.4973(3) -0.10774(11) 0.0168(5) Uani 1 1 d . . . . .
H12A H 0.4992 0.4379 -0.1431 0.020 Uiso 1 1 calc R . . . .
C13A C 0.1513(3) 0.4150(3) 0.07112(12) 0.0243(6) Uani 1 1 d . . . . .
H13D H 0.2257 0.3818 0.0976 0.036 Uiso 1 1 calc GR . . . .
H13E H 0.0842 0.3377 0.0646 0.036 Uiso 1 1 calc GR . . . .
H13F H 0.1046 0.4970 0.0887 0.036 Uiso 1 1 calc GR . . . .
C14A C 0.2138(3) 0.7885(3) -0.18173(14) 0.0302(7) Uani 1 1 d . . . . .
H14D H 0.1930 0.7165 -0.2118 0.045 Uiso 1 1 calc GR . . . .
H14E H 0.2499 0.8749 -0.2004 0.045 Uiso 1 1 calc GR . . . .
H14F H 0.1290 0.8120 -0.1607 0.045 Uiso 1 1 calc GR . . . .
C15A C 0.7665(3) 0.3925(3) -0.10041(12) 0.0233(6) Uani 1 1 d . . . . .
H15D H 0.8155 0.4840 -0.1024 0.035 Uiso 1 1 calc GR . . . .
H15E H 0.7508 0.3555 -0.1402 0.035 Uiso 1 1 calc GR . . . .
H15F H 0.8226 0.3241 -0.0777 0.035 Uiso 1 1 calc GR . . . .
O20A O 0.62904(19) 0.6131(2) 0.14294(8) 0.0239(4) Uani 1 1 d . . . . .
O21A O 0.84393(19) 0.6097(2) 0.10633(8) 0.0224(4) Uani 1 1 d . . . . .
H21A H 0.796(5) 0.562(5) 0.078(2) 0.053(13) Uiso 1 1 d . . . . .
C20A C 0.7497(3) 0.6511(3) 0.14444(12) 0.0198(5) Uani 1 1 d . . . . .
C21A C 0.8084(3) 0.7506(3) 0.18992(11) 0.0194(5) Uani 1 1 d . . . . .
C22A C 0.7286(3) 0.7875(4) 0.23780(13) 0.0271(6) Uani 1 1 d . . . . .
H22A H 0.6388 0.7474 0.2420 0.032 Uiso 1 1 calc R . . . .
C23A C 0.7800(3) 0.8830(4) 0.27950(13) 0.0335(7) Uani 1 1 d . . . . .
H23A H 0.7260 0.9069 0.3125 0.040 Uiso 1 1 calc R . . . .
C24A C 0.9104(3) 0.9433(4) 0.27279(13) 0.0301(7) Uani 1 1 d . . . . .
H24A H 0.9452 1.0094 0.3010 0.036 Uiso 1 1 calc R . . . .
C25A C 0.9898(3) 0.9071(3) 0.22499(12) 0.0235(6) Uani 1 1 d . . . . .
H25A H 1.0787 0.9490 0.2203 0.028 Uiso 1 1 calc R . . . .
C26A C 0.9398(3) 0.8100(3) 0.18404(11) 0.0199(5) Uani 1 1 d . . . . .
H26A H 0.9954 0.7838 0.1518 0.024 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 O2 1.470(3) . ?
O1 C1 1.462(3) . ?
O2 C3 1.417(3) . ?
O3 C2 1.418(3) . ?
O3 C3 1.433(4) . ?
O10 C10 1.250(3) . ?
N11 C2 1.460(3) . ?
N11 C10 1.333(4) . ?
C1 C2 1.526(4) . ?
C1 C11 1.546(3) . ?
C1 C12 1.536(3) . ?
C3 C4 1.538(4) . ?
C3 C13 1.512(4) . ?
C4 C5 1.529(4) . ?
C5 C11 1.542(4) . ?
C6 C7 1.528(4) . ?
C6 C11 1.543(4) . ?
C6 C14 1.535(4) . ?
C7 C8 1.526(4) . ?
C8 C12 1.538(4) . ?
C9 C10 1.508(4) . ?
C9 C12 1.536(4) . ?
C9 C15 1.530(4) . ?
O20 C20 1.220(4) . ?
O21 C20 1.322(4) . ?
C20 C21 1.492(4) . ?
C21 C22 1.392(4) . ?
C21 C26 1.393(4) . ?
C22 C23 1.381(4) . ?
C23 C24 1.390(5) . ?
C24 C25 1.389(5) . ?
C25 C26 1.388(4) . ?
O1A O2A 1.471(2) . ?
O1A C1A 1.456(3) . ?
O2A C3A 1.414(3) . ?
O3A C2A 1.417(3) . ?
O3A C3A 1.439(3) . ?
O10A C10A 1.242(3) . ?
N11A C2A 1.463(3) . ?
N11A C10A 1.339(3) . ?
C1A C2A 1.533(3) . ?
C1A C11A 1.541(3) . ?
C1A C12A 1.535(3) . ?
C3A C4A 1.535(4) . ?
C3A C13A 1.511(4) . ?
C4A C5A 1.524(4) . ?
C5A C11A 1.542(4) . ?
C6A C7A 1.528(4) . ?
C6A C11A 1.542(4) . ?
C6A C14A 1.533(4) . ?
C7A C8A 1.524(4) . ?
C8A C12A 1.526(4) . ?
C9A C10A 1.523(3) . ?
C9A C12A 1.530(3) . ?
C9A C15A 1.523(3) . ?
O20A C20A 1.217(3) . ?
O21A C20A 1.326(3) . ?
C20A C21A 1.498(4) . ?
C21A C22A 1.390(4) . ?
C21A C26A 1.392(4) . ?
C22A C23A 1.391(5) . ?
C23A C24A 1.390(4) . ?
C24A C25A 1.385(4) . ?
C25A C26A 1.384(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 O2 112.02(18) . . ?
C3 O2 O1 107.87(18) . . ?
C2 O3 C3 113.4(2) . . ?
C10 N11 C2 126.6(2) . . ?
O1 C1 C2 110.1(2) . . ?
O1 C1 C11 107.2(2) . . ?
O1 C1 C12 104.2(2) . . ?
C2 C1 C11 112.1(2) . . ?
C2 C1 C12 110.8(2) . . ?
C12 C1 C11 112.1(2) . . ?
O3 C2 N11 108.3(2) . . ?
O3 C2 C1 113.6(2) . . ?
N11 C2 C1 112.2(2) . . ?
O2 C3 O3 108.0(2) . . ?
O2 C3 C4 111.8(2) . . ?
O2 C3 C13 104.8(2) . . ?
O3 C3 C4 110.9(2) . . ?
O3 C3 C13 107.0(2) . . ?
C13 C3 C4 113.8(2) . . ?
C5 C4 C3 113.9(2) . . ?
C4 C5 C11 115.8(2) . . ?
C7 C6 C11 111.9(2) . . ?
C7 C6 C14 109.7(2) . . ?
C14 C6 C11 110.9(2) . . ?
C8 C7 C6 112.5(2) . . ?
C7 C8 C12 110.5(2) . . ?
C10 C9 C12 113.1(2) . . ?
C10 C9 C15 111.3(2) . . ?
C15 C9 C12 114.1(2) . . ?
O10 C10 N11 120.4(2) . . ?
O10 C10 C9 119.9(2) . . ?
N11 C10 C9 119.5(2) . . ?
C5 C11 C1 111.9(2) . . ?
C5 C11 C6 110.7(2) . . ?
C6 C11 C1 112.3(2) . . ?
C1 C12 C8 110.0(2) . . ?
C1 C12 C9 110.4(2) . . ?
C9 C12 C8 115.1(2) . . ?
O20 C20 O21 124.0(3) . . ?
O20 C20 C21 123.3(3) . . ?
O21 C20 C21 112.8(2) . . ?
C22 C21 C20 119.0(3) . . ?
C22 C21 C26 119.8(3) . . ?
C26 C21 C20 121.2(3) . . ?
C23 C22 C21 120.0(3) . . ?
C22 C23 C24 120.4(3) . . ?
C25 C24 C23 119.7(3) . . ?
C26 C25 C24 120.1(3) . . ?
C25 C26 C21 120.0(3) . . ?
C1A O1A O2A 112.26(17) . . ?
C3A O2A O1A 107.61(18) . . ?
C2A O3A C3A 113.45(19) . . ?
C10A N11A C2A 126.7(2) . . ?
O1A C1A C2A 110.5(2) . . ?
O1A C1A C11A 107.4(2) . . ?
O1A C1A C12A 104.3(2) . . ?
C2A C1A C11A 111.6(2) . . ?
C2A C1A C12A 111.0(2) . . ?
C12A C1A C11A 111.8(2) . . ?
O3A C2A N11A 108.6(2) . . ?
O3A C2A C1A 113.8(2) . . ?
N11A C2A C1A 112.6(2) . . ?
O2A C3A O3A 107.51(19) . . ?
O2A C3A C4A 112.4(2) . . ?
O2A C3A C13A 105.1(2) . . ?
O3A C3A C4A 111.1(2) . . ?
O3A C3A C13A 107.6(2) . . ?
C13A C3A C4A 112.9(2) . . ?
C5A C4A C3A 114.6(2) . . ?
C4A C5A C11A 115.7(2) . . ?
C7A C6A C11A 111.9(2) . . ?
C7A C6A C14A 109.8(2) . . ?
C14A C6A C11A 110.9(2) . . ?
C8A C7A C6A 112.5(2) . . ?
C7A C8A C12A 110.4(2) . . ?
C10A C9A C12A 112.6(2) . . ?
C10A C9A C15A 111.4(2) . . ?
C15A C9A C12A 114.1(2) . . ?
O10A C10A N11A 121.5(2) . . ?
O10A C10A C9A 120.2(2) . . ?
N11A C10A C9A 118.2(2) . . ?
C1A C11A C5A 111.9(2) . . ?
C1A C11A C6A 112.9(2) . . ?
C5A C11A C6A 111.1(2) . . ?
C8A C12A C1A 110.7(2) . . ?
C8A C12A C9A 115.0(2) . . ?
C9A C12A C1A 109.8(2) . . ?
O20A C20A O21A 124.2(3) . . ?
O20A C20A C21A 123.5(3) . . ?
O21A C20A C21A 112.4(2) . . ?
C22A C21A C20A 119.4(3) . . ?
C22A C21A C26A 119.5(3) . . ?
C26A C21A C20A 121.0(2) . . ?
C21A C22A C23A 120.1(3) . . ?
C24A C23A C22A 119.9(3) . . ?
C25A C24A C23A 120.0(3) . . ?
C26A C25A C24A 120.1(3) . . ?
C25A C26A C21A 120.3(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
N11 H11 O20 0.90(4) 2.06(3) 2.958(3) 170(3) .
O21 H21 O10 0.87(4) 1.71(4) 2.572(3) 171(4) .
N11A H11B O20A 0.89(4) 2.23(4) 3.109(3) 169(3) .
O21A H21A O10A 0.91(5) 1.71(5) 2.596(3) 162(4) .

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 O2 C3 O3 -75.0(2) . . . . ?
O1 O2 C3 C4 47.3(3) . . . . ?
O1 O2 C3 C13 171.1(2) . . . . ?
O1 C1 C2 O3 -53.0(3) . . . . ?
O1 C1 C2 N11 70.3(3) . . . . ?
O1 C1 C11 C5 69.1(3) . . . . ?
O1 C1 C11 C6 -165.7(2) . . . . ?
O1 C1 C12 C8 171.6(2) . . . . ?
O1 C1 C12 C9 -60.3(3) . . . . ?
O2 O1 C1 C2 14.7(3) . . . . ?
O2 O1 C1 C11 -107.5(2) . . . . ?
O2 O1 C1 C12 133.51(19) . . . . ?
O2 C3 C4 C5 -96.7(3) . . . . ?
O3 C3 C4 C5 23.9(3) . . . . ?
C1 O1 O2 C3 46.1(3) . . . . ?
C2 O3 C3 O2 35.7(3) . . . . ?
C2 O3 C3 C4 -87.2(3) . . . . ?
C2 O3 C3 C13 148.1(2) . . . . ?
C2 N11 C10 O10 172.7(2) . . . . ?
C2 N11 C10 C9 -11.5(4) . . . . ?
C2 C1 C11 C5 -51.8(3) . . . . ?
C2 C1 C11 C6 73.4(3) . . . . ?
C2 C1 C12 C8 -70.0(3) . . . . ?
C2 C1 C12 C9 58.1(3) . . . . ?
C3 O3 C2 N11 -98.8(2) . . . . ?
C3 O3 C2 C1 26.5(3) . . . . ?
C3 C4 C5 C11 59.1(3) . . . . ?
C4 C5 C11 C1 -37.7(3) . . . . ?
C4 C5 C11 C6 -163.8(2) . . . . ?
C6 C7 C8 C12 57.4(3) . . . . ?
C7 C6 C11 C1 49.5(3) . . . . ?
C7 C6 C11 C5 175.4(2) . . . . ?
C7 C8 C12 C1 -58.4(3) . . . . ?
C7 C8 C12 C9 176.2(2) . . . . ?
C10 N11 C2 O3 148.3(3) . . . . ?
C10 N11 C2 C1 22.1(4) . . . . ?
C10 C9 C12 C1 -46.9(3) . . . . ?
C10 C9 C12 C8 78.4(3) . . . . ?
C11 C1 C2 O3 66.2(3) . . . . ?
C11 C1 C2 N11 -170.5(2) . . . . ?
C11 C1 C12 C8 56.1(3) . . . . ?
C11 C1 C12 C9 -175.8(2) . . . . ?
C11 C6 C7 C8 -52.7(3) . . . . ?
C12 C1 C2 O3 -167.7(2) . . . . ?
C12 C1 C2 N11 -44.5(3) . . . . ?
C12 C1 C11 C5 -177.1(2) . . . . ?
C12 C1 C11 C6 -51.9(3) . . . . ?
C12 C9 C10 O10 -160.4(2) . . . . ?
C12 C9 C10 N11 23.7(3) . . . . ?
C13 C3 C4 C5 144.6(3) . . . . ?
C14 C6 C7 C8 -176.3(2) . . . . ?
C14 C6 C11 C1 172.4(2) . . . . ?
C14 C6 C11 C5 -61.7(3) . . . . ?
C15 C9 C10 O10 -30.5(4) . . . . ?
C15 C9 C10 N11 153.6(3) . . . . ?
C15 C9 C12 C1 -175.4(2) . . . . ?
C15 C9 C12 C8 -50.1(3) . . . . ?
O20 C20 C21 C22 -0.9(4) . . . . ?
O20 C20 C21 C26 -178.9(3) . . . . ?
O21 C20 C21 C22 179.0(3) . . . . ?
O21 C20 C21 C26 1.0(4) . . . . ?
C20 C21 C22 C23 -176.9(3) . . . . ?
C20 C21 C26 C25 176.6(3) . . . . ?
C21 C22 C23 C24 -0.2(4) . . . . ?
C22 C21 C26 C25 -1.4(4) . . . . ?
C22 C23 C24 C25 -0.4(5) . . . . ?
C23 C24 C25 C26 0.1(5) . . . . ?
C24 C25 C26 C21 0.7(5) . . . . ?
C26 C21 C22 C23 1.1(4) . . . . ?
O1A O2A C3A O3A -75.9(2) . . . . ?
O1A O2A C3A C4A 46.7(3) . . . . ?
O1A O2A C3A C13A 169.75(19) . . . . ?
O1A C1A C2A O3A -51.2(3) . . . . ?
O1A C1A C2A N11A 73.0(3) . . . . ?
O1A C1A C11A C5A 69.1(3) . . . . ?
O1A C1A C11A C6A -164.6(2) . . . . ?
O1A C1A C12A C8A 171.3(2) . . . . ?
O1A C1A C12A C9A -60.7(2) . . . . ?
O2A O1A C1A C2A 14.2(3) . . . . ?
O2A O1A C1A C11A -107.7(2) . . . . ?
O2A O1A C1A C12A 133.57(18) . . . . ?
O2A C3A C4A C5A -96.1(3) . . . . ?
O3A C3A C4A C5A 24.4(3) . . . . ?
C1A O1A O2A C3A 46.3(2) . . . . ?
C2A O3A C3A O2A 37.7(3) . . . . ?
C2A O3A C3A C4A -85.6(3) . . . . ?
C2A O3A C3A C13A 150.4(2) . . . . ?
C2A N11A C10A O10A 169.0(2) . . . . ?
C2A N11A C10A C9A -15.2(4) . . . . ?
C2A C1A C11A C5A -52.1(3) . . . . ?
C2A C1A C11A C6A 74.1(3) . . . . ?
C2A C1A C12A C8A -69.7(3) . . . . ?
C2A C1A C12A C9A 58.3(3) . . . . ?
C3A O3A C2A N11A -102.4(2) . . . . ?
C3A O3A C2A C1A 23.9(3) . . . . ?
C3A C4A C5A C11A 58.5(3) . . . . ?
C4A C5A C11A C1A -37.4(3) . . . . ?
C4A C5A C11A C6A -164.6(2) . . . . ?
C6A C7A C8A C12A 57.4(3) . . . . ?
C7A C6A C11A C1A 48.7(3) . . . . ?
C7A C6A C11A C5A 175.4(2) . . . . ?
C7A C8A C12A C1A -58.6(3) . . . . ?
C7A C8A C12A C9A 176.3(2) . . . . ?
C10A N11A C2A O3A 148.5(2) . . . . ?
C10A N11A C2A C1A 21.6(4) . . . . ?
C10A C9A C12A C1A -51.3(3) . . . . ?
C10A C9A C12A C8A 74.3(3) . . . . ?
C11A C1A C2A O3A 68.2(3) . . . . ?
C11A C1A C2A N11A -167.6(2) . . . . ?
C11A C1A C12A C8A 55.6(3) . . . . ?
C11A C1A C12A C9A -176.4(2) . . . . ?
C11A C6A C7A C8A -52.2(3) . . . . ?
C12A C1A C2A O3A -166.4(2) . . . . ?
C12A C1A C2A N11A -42.2(3) . . . . ?
C12A C1A C11A C5A -177.1(2) . . . . ?
C12A C1A C11A C6A -50.8(3) . . . . ?
C12A C9A C10A O10A -154.4(2) . . . . ?
C12A C9A C10A N11A 29.8(3) . . . . ?
C13A C3A C4A C5A 145.3(2) . . . . ?
C14A C6A C7A C8A -175.7(2) . . . . ?
C14A C6A C11A C1A 171.6(2) . . . . ?
C14A C6A C11A C5A -61.6(3) . . . . ?
C15A C9A C10A O10A -24.7(4) . . . . ?
C15A C9A C10A N11A 159.5(2) . . . . ?
C15A C9A C12A C1A -179.5(2) . . . . ?
C15A C9A C12A C8A -54.0(3) . . . . ?
O20A C20A C21A C22A 9.2(4) . . . . ?
O20A C20A C21A C26A -168.8(3) . . . . ?
O21A C20A C21A C22A -170.8(2) . . . . ?
O21A C20A C21A C26A 11.2(3) . . . . ?
C20A C21A C22A C23A -178.1(3) . . . . ?
C20A C21A C26A C25A 176.8(3) . . . . ?
C21A C22A C23A C24A 1.0(5) . . . . ?
C22A C21A C26A C25A -1.1(4) . . . . ?
C22A C23A C24A C25A -0.7(5) . . . . ?
C23A C24A C25A C26A -0.5(5) . . . . ?
C24A C25A C26A C21A 1.4(4) . . . . ?
C26A C21A C22A C23A -0.1(4) . . . . ?

_olex2_date_sample_data_collection 2017-06-26
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.176
_oxdiff_exptl_absorpt_empirical_full_min 0.888
####################################################################### 
# 
# 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_cpd3_madiha26cult
_database_code_depnum_ccdc_archive 'CCDC 1569110'
_audit_update_record             
;
2017-08-15 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2017-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            11-Aza:Sal
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H23 N O4, C7 H6 O3'
_chemical_formula_sum            'C22 H29 N O7'
_chemical_formula_weight         419.46
_chemical_absolute_configuration ad
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.79451(14)
_cell_length_b                   9.30687(13)
_cell_length_c                   11.51291(16)
_cell_angle_alpha                90
_cell_angle_beta                 92.3070(12)
_cell_angle_gamma                90
_cell_volume                     1048.62(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6402
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.2640
_cell_measurement_theta_min      3.8220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.820
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40396
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8079
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.996
_diffrn_reflns_theta_min         3.843
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -35.00  36.00   1.00    1.00    --   40.45 -37.00   0.00   71
  2  ω     15.00  68.00   1.00    1.00    --   40.45  37.00-120.00   53
  3  ω     29.00  92.00   1.00    1.00    --   40.45  57.00 -90.00   63
  4  ω    145.00 176.00   1.00    2.00    --  110.57 125.00 -90.00   31
  5  ω    121.00 148.00   1.00    2.00    --  110.57  45.00-180.00   27
  6  ω     95.00 140.00   1.00    2.00    --  110.57 125.00 -90.00   45
  7  ω     83.00 112.00   1.00    2.00    --  110.57  45.00-180.00   29
  8  ω     85.00 119.00   1.00    2.00    --  110.57  30.00-150.00   34
  9  ω     86.00 173.00   1.00    2.00    --  110.57  30.00 -90.00   87
 10  ω    132.00 159.00   1.00    2.00    --  110.57  61.00  90.00   27
 11  ω    121.00 174.00   1.00    2.00    --  110.57  77.00 120.00   53
 12  ω    112.00 174.00   1.00    2.00    --  110.57  77.00  90.00   62
 13  ω     87.00 116.00   1.00    1.00    --   40.45  37.00 150.00   29
 14  ω     78.00 104.00   1.00    2.00    --  110.57  77.00  60.00   26
 15  ω     77.00 104.00   1.00    2.00    --  110.57  77.00  90.00   27
 16  ω     77.00 104.00   1.00    2.00    --  110.57  77.00 120.00   27
 17  ω     84.00 109.00   1.00    2.00    --  110.57  45.00 150.00   25
 18  ω     83.00 109.00   1.00    2.00    --  110.57  45.00 120.00   26
 19  ω     82.00 110.00   1.00    2.00    --  110.57  61.00 150.00   28
 20  ω     86.00 117.00   1.00    2.00    --  110.57  30.00 120.00   31
 21  ω     81.00 107.00   1.00    2.00    --  110.57  61.00  60.00   26
 22  ω     80.00 106.00   1.00    2.00    --  110.57  61.00  90.00   26
 23  ω     80.00 107.00   1.00    2.00    --  110.57  61.00 120.00   27
 24  ω     77.00 104.00   1.00    2.00    --  110.57  77.00 150.00   27
 25  ω     19.00  79.00   1.00    1.00    --   40.45  37.00 150.00   60
 26  ω     28.00 106.00   1.00    2.00    --  110.57 -94.00  30.00   78
 27  ω     37.00 109.00   1.00    2.00    --  110.57-125.00 -90.00   72
 28  ω     12.00  56.00   1.00    1.00    --   40.45  57.00-150.00   44
 29  ω     77.00 160.00   1.00    2.00    --  110.57  77.00-180.00   83
 30  ω     80.00 107.00   1.00    2.00    --  110.57  61.00-180.00   27
 31  ω    -61.00  21.00   1.00    1.00    --  -40.45  37.00  30.00   82
 32  ω    -67.00  28.00   1.00    1.00    --  -40.45  57.00 120.00   95
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0349412000
_diffrn_orient_matrix_UB_12      0.0492318000
_diffrn_orient_matrix_UB_13      -0.1229416000
_diffrn_orient_matrix_UB_21      0.1497918000
_diffrn_orient_matrix_UB_22      -0.0454822000
_diffrn_orient_matrix_UB_23      0.0238388000
_diffrn_orient_matrix_UB_31      -0.0336577000
_diffrn_orient_matrix_UB_32      -0.1514253000
_diffrn_orient_matrix_UB_33      -0.0472241000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_full    0.925
_reflns_Friedel_fraction_max     0.926
_reflns_number_gt                3518
_reflns_number_total             3602
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1534 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         3602
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0273
_refine_ls_restrained_S_all      1.004
_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)+(0.0400P)²+0.1300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0680
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6), C9(H9), C11(H11A), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C24(H24), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.44406(13) 0.87991(15) 0.34235(12) 0.0174(3) Uani 1 1 d . . . . .
O2 O 0.58944(13) 0.89286(15) 0.38023(12) 0.0188(3) Uani 1 1 d . . . . .
O3 O 0.62883(13) 0.64895(15) 0.39291(11) 0.0170(3) Uani 1 1 d . . . . .
O10 O 0.39897(14) 0.77832(16) 0.71264(11) 0.0213(3) Uani 1 1 d . . . . .
N11 N 0.49469(16) 0.69462(18) 0.55164(14) 0.0158(3) Uani 1 1 d . . . . .
H11 H 0.568(3) 0.668(3) 0.595(2) 0.035(7) Uiso 1 1 d . . . . .
C1 C 0.39365(19) 0.7331(2) 0.35469(16) 0.0147(4) Uani 1 1 d . . . . .
C2 C 0.49397(18) 0.6463(2) 0.43154(15) 0.0149(4) Uani 1 1 d . . . . .
H2 H 0.4625 0.5440 0.4299 0.018 Uiso 1 1 calc R . . . .
C3 C 0.6614(2) 0.7772(2) 0.33061(17) 0.0184(4) Uani 1 1 d . . . . .
C4 C 0.6250(2) 0.7610(2) 0.20055(17) 0.0218(4) Uani 1 1 d . . . . .
H4A H 0.5936 0.8552 0.1696 0.026 Uiso 1 1 calc R . . . .
H4B H 0.7085 0.7343 0.1600 0.026 Uiso 1 1 calc R . . . .
C5 C 0.5145(2) 0.6490(2) 0.17279(16) 0.0194(4) Uani 1 1 d . . . . .
H5A H 0.5516 0.5534 0.1947 0.023 Uiso 1 1 calc R . . . .
H5B H 0.4962 0.6484 0.0876 0.023 Uiso 1 1 calc R . . . .
C6 C 0.2968(2) 0.5262(2) 0.23050(17) 0.0200(4) Uani 1 1 d . . . . .
H6 H 0.3531 0.4532 0.2745 0.024 Uiso 1 1 calc R . . . .
C7 C 0.1623(2) 0.5431(2) 0.29110(18) 0.0228(4) Uani 1 1 d . . . . .
H7A H 0.1171 0.4482 0.2952 0.027 Uiso 1 1 calc R . . . .
H7B H 0.1014 0.6076 0.2444 0.027 Uiso 1 1 calc R . . . .
C8 C 0.1816(2) 0.6041(2) 0.41390(17) 0.0199(4) Uani 1 1 d . . . . .
H8A H 0.2351 0.5354 0.4632 0.024 Uiso 1 1 calc R . . . .
H8B H 0.0913 0.6168 0.4481 0.024 Uiso 1 1 calc R . . . .
C9 C 0.27556(19) 0.8219(2) 0.53182(17) 0.0166(4) Uani 1 1 d . . . . .
H9 H 0.3014 0.9237 0.5155 0.020 Uiso 1 1 calc R . . . .
C10 C 0.39332(19) 0.7600(2) 0.60523(16) 0.0160(4) Uani 1 1 d . . . . .
C11 C 0.3773(2) 0.6682(2) 0.23154(16) 0.0177(4) Uani 1 1 d . . . . .
H11A H 0.3224 0.7382 0.1832 0.021 Uiso 1 1 calc R . . . .
C12 C 0.25624(19) 0.7490(2) 0.41226(16) 0.0158(4) Uani 1 1 d . . . . .
H12 H 0.1990 0.8150 0.3621 0.019 Uiso 1 1 calc R . . . .
C13 C 0.8107(2) 0.8083(2) 0.3584(2) 0.0256(5) Uani 1 1 d . . . . .
H13A H 0.8250 0.8229 0.4423 0.038 Uiso 1 1 calc GR . . . .
H13B H 0.8378 0.8951 0.3170 0.038 Uiso 1 1 calc GR . . . .
H13C H 0.8661 0.7269 0.3338 0.038 Uiso 1 1 calc GR . . . .
C14 C 0.2711(2) 0.4703(2) 0.10674(18) 0.0252(5) Uani 1 1 d . . . . .
H14A H 0.2227 0.5437 0.0599 0.038 Uiso 1 1 calc GR . . . .
H14B H 0.2155 0.3829 0.1086 0.038 Uiso 1 1 calc GR . . . .
H14C H 0.3586 0.4486 0.0723 0.038 Uiso 1 1 calc GR . . . .
C15 C 0.1454(2) 0.8302(3) 0.60026(19) 0.0256(5) Uani 1 1 d . . . . .
H15A H 0.0705 0.8674 0.5499 0.038 Uiso 1 1 calc GR . . . .
H15B H 0.1604 0.8943 0.6670 0.038 Uiso 1 1 calc GR . . . .
H15C H 0.1218 0.7340 0.6277 0.038 Uiso 1 1 calc GR . . . .
O20 O 0.71925(14) 0.65940(16) 0.72267(11) 0.0206(3) Uani 1 1 d . . . . .
O21 O 0.55438(14) 0.63049(16) 0.84944(12) 0.0223(3) Uani 1 1 d . . . . .
H21 H 0.502(3) 0.686(4) 0.794(3) 0.050(9) Uiso 1 1 d . . . . .
O22 O 0.95395(15) 0.53982(18) 0.76182(13) 0.0247(3) Uani 1 1 d . . . . .
H22 H 0.891(3) 0.589(3) 0.730(2) 0.036(8) Uiso 1 1 d . . . . .
C20 C 0.6769(2) 0.6062(2) 0.81323(16) 0.0183(4) Uani 1 1 d . . . . .
C21 C 0.7633(2) 0.5105(2) 0.88715(17) 0.0181(4) Uani 1 1 d . . . . .
C22 C 0.8975(2) 0.4803(2) 0.85602(17) 0.0194(4) Uani 1 1 d . . . . .
C23 C 0.9775(2) 0.3853(3) 0.92374(18) 0.0240(4) Uani 1 1 d . . . . .
H23 H 1.0683 0.3644 0.9030 0.029 Uiso 1 1 calc R . . . .
C24 C 0.9248(2) 0.3219(2) 1.02073(19) 0.0260(5) Uani 1 1 d . . . . .
H24 H 0.9800 0.2577 1.0664 0.031 Uiso 1 1 calc R . . . .
C25 C 0.7916(2) 0.3508(2) 1.05258(18) 0.0242(5) Uani 1 1 d . . . . .
H25 H 0.7560 0.3070 1.1194 0.029 Uiso 1 1 calc R . . . .
C26 C 0.7123(2) 0.4441(2) 0.98551(17) 0.0208(4) Uani 1 1 d . . . . .
H26 H 0.6213 0.4637 1.0065 0.025 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 O2 1.4772(18) . ?
O1 C1 1.462(2) . ?
O2 C3 1.419(2) . ?
O3 C2 1.411(2) . ?
O3 C3 1.436(2) . ?
O10 C10 1.247(2) . ?
N11 C2 1.454(2) . ?
N11 C10 1.336(3) . ?
C1 C2 1.527(2) . ?
C1 C11 1.543(3) . ?
C1 C12 1.531(3) . ?
C3 C4 1.533(3) . ?
C3 C13 1.512(3) . ?
C4 C5 1.527(3) . ?
C5 C11 1.538(3) . ?
C6 C7 1.523(3) . ?
C6 C11 1.539(3) . ?
C6 C14 1.528(3) . ?
C7 C8 1.528(3) . ?
C8 C12 1.534(3) . ?
C9 C10 1.516(3) . ?
C9 C12 1.540(3) . ?
C9 C15 1.527(3) . ?
O20 C20 1.241(2) . ?
O21 C20 1.306(2) . ?
O22 C22 1.355(3) . ?
C20 C21 1.475(3) . ?
C21 C22 1.405(3) . ?
C21 C26 1.400(3) . ?
C22 C23 1.398(3) . ?
C23 C24 1.381(3) . ?
C24 C25 1.396(3) . ?
C25 C26 1.380(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 O2 111.90(13) . . ?
C3 O2 O1 107.94(13) . . ?
C2 O3 C3 113.72(14) . . ?
C10 N11 C2 127.21(16) . . ?
O1 C1 C2 109.82(15) . . ?
O1 C1 C11 107.42(15) . . ?
O1 C1 C12 104.96(14) . . ?
C2 C1 C11 111.44(15) . . ?
C2 C1 C12 110.89(15) . . ?
C12 C1 C11 112.03(15) . . ?
O3 C2 N11 109.00(14) . . ?
O3 C2 C1 113.37(15) . . ?
N11 C2 C1 111.45(15) . . ?
O2 C3 O3 107.78(14) . . ?
O2 C3 C4 111.58(16) . . ?
O2 C3 C13 105.20(16) . . ?
O3 C3 C4 111.00(16) . . ?
O3 C3 C13 106.62(16) . . ?
C13 C3 C4 114.25(16) . . ?
C5 C4 C3 114.01(16) . . ?
C4 C5 C11 116.92(16) . . ?
C7 C6 C11 111.15(16) . . ?
C7 C6 C14 110.43(17) . . ?
C14 C6 C11 111.39(17) . . ?
C6 C7 C8 112.61(16) . . ?
C7 C8 C12 110.90(16) . . ?
C10 C9 C12 113.22(16) . . ?
C10 C9 C15 111.32(16) . . ?
C15 C9 C12 114.10(16) . . ?
O10 C10 N11 121.05(18) . . ?
O10 C10 C9 120.21(17) . . ?
N11 C10 C9 118.58(16) . . ?
C5 C11 C1 112.92(15) . . ?
C5 C11 C6 110.70(16) . . ?
C6 C11 C1 112.16(16) . . ?
C1 C12 C8 110.36(15) . . ?
C1 C12 C9 110.55(15) . . ?
C8 C12 C9 114.71(15) . . ?
O20 C20 O21 122.80(18) . . ?
O20 C20 C21 121.49(18) . . ?
O21 C20 C21 115.71(18) . . ?
C22 C21 C20 119.65(18) . . ?
C26 C21 C20 121.18(18) . . ?
C26 C21 C22 119.12(18) . . ?
O22 C22 C21 122.57(19) . . ?
O22 C22 C23 117.84(18) . . ?
C23 C22 C21 119.58(19) . . ?
C24 C23 C22 120.10(19) . . ?
C23 C24 C25 120.9(2) . . ?
C26 C25 C24 119.1(2) . . ?
C25 C26 C21 121.24(19) . . ?

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
N11 H11 O20 0.89(3) 2.05(3) 2.911(2) 163(3) .
O21 H21 O10 0.95(4) 1.60(4) 2.5490(19) 173(3) .
O22 H22 O20 0.84(3) 1.81(3) 2.577(2) 152(3) .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 O2 C3 O3 -74.26(16) . . . . ?
O1 O2 C3 C4 47.85(19) . . . . ?
O1 O2 C3 C13 172.26(14) . . . . ?
O1 C1 C2 O3 -54.1(2) . . . . ?
O1 C1 C2 N11 69.29(19) . . . . ?
O1 C1 C11 C5 66.16(19) . . . . ?
O1 C1 C11 C6 -167.93(15) . . . . ?
O1 C1 C12 C8 171.55(15) . . . . ?
O1 C1 C12 C9 -60.48(18) . . . . ?
O2 O1 C1 C2 14.66(19) . . . . ?
O2 O1 C1 C11 -106.70(15) . . . . ?
O2 O1 C1 C12 133.91(13) . . . . ?
O2 C3 C4 C5 -96.2(2) . . . . ?
O3 C3 C4 C5 24.0(2) . . . . ?
C1 O1 O2 C3 46.36(17) . . . . ?
C2 O3 C3 O2 34.0(2) . . . . ?
C2 O3 C3 C4 -88.51(18) . . . . ?
C2 O3 C3 C13 146.48(15) . . . . ?
C2 N11 C10 O10 169.84(19) . . . . ?
C2 N11 C10 C9 -14.7(3) . . . . ?
C2 C1 C11 C5 -54.2(2) . . . . ?
C2 C1 C11 C6 71.7(2) . . . . ?
C2 C1 C12 C8 -69.92(19) . . . . ?
C2 C1 C12 C9 58.1(2) . . . . ?
C3 O3 C2 N11 -96.23(17) . . . . ?
C3 O3 C2 C1 28.5(2) . . . . ?
C3 C4 C5 C11 56.3(2) . . . . ?
C4 C5 C11 C1 -33.9(2) . . . . ?
C4 C5 C11 C6 -160.56(17) . . . . ?
C6 C7 C8 C12 56.7(2) . . . . ?
C7 C6 C11 C1 51.5(2) . . . . ?
C7 C6 C11 C5 178.62(16) . . . . ?
C7 C8 C12 C1 -56.6(2) . . . . ?
C7 C8 C12 C9 177.72(16) . . . . ?
C10 N11 C2 O3 151.69(18) . . . . ?
C10 N11 C2 C1 25.8(3) . . . . ?
C10 C9 C12 C1 -46.2(2) . . . . ?
C10 C9 C12 C8 79.4(2) . . . . ?
C11 C1 C2 O3 64.8(2) . . . . ?
C11 C1 C2 N11 -171.80(15) . . . . ?
C11 C1 C12 C8 55.29(19) . . . . ?
C11 C1 C12 C9 -176.73(15) . . . . ?
C11 C6 C7 C8 -53.7(2) . . . . ?
C12 C1 C2 O3 -169.68(14) . . . . ?
C12 C1 C2 N11 -46.3(2) . . . . ?
C12 C1 C11 C5 -179.08(15) . . . . ?
C12 C1 C11 C6 -53.2(2) . . . . ?
C12 C9 C10 O10 -160.19(17) . . . . ?
C12 C9 C10 N11 24.4(2) . . . . ?
C13 C3 C4 C5 144.59(18) . . . . ?
C14 C6 C7 C8 -177.87(18) . . . . ?
C14 C6 C11 C1 175.12(16) . . . . ?
C14 C6 C11 C5 -57.8(2) . . . . ?
C15 C9 C10 O10 -30.1(3) . . . . ?
C15 C9 C10 N11 154.46(18) . . . . ?
C15 C9 C12 C1 -174.86(16) . . . . ?
C15 C9 C12 C8 -49.3(2) . . . . ?
O20 C20 C21 C22 1.1(3) . . . . ?
O20 C20 C21 C26 -176.24(18) . . . . ?
O21 C20 C21 C22 -178.88(17) . . . . ?
O21 C20 C21 C26 3.8(3) . . . . ?
O22 C22 C23 C24 179.9(2) . . . . ?
C20 C21 C22 O22 2.4(3) . . . . ?
C20 C21 C22 C23 -177.60(18) . . . . ?
C20 C21 C26 C25 177.83(19) . . . . ?
C21 C22 C23 C24 -0.1(3) . . . . ?
C22 C21 C26 C25 0.5(3) . . . . ?
C22 C23 C24 C25 0.2(3) . . . . ?
C23 C24 C25 C26 0.1(3) . . . . ?
C24 C25 C26 C21 -0.4(3) . . . . ?
C26 C21 C22 O22 179.75(18) . . . . ?
C26 C21 C22 C23 -0.2(3) . . . . ?

_olex2_date_sample_data_collection 2017-05-10
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.758
_oxdiff_exptl_absorpt_empirical_full_min 0.386
####################################################################### 
# 
# 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_cpd5_madiha28a
_database_code_depnum_ccdc_archive 'CCDC 1569112'
_audit_update_record             
;
2017-08-15 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2017-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            11-Aza:Succ
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C15 H23 N O4), C4 H6 O4'
_chemical_formula_sum            'C34 H52 N2 O12'
_chemical_formula_weight         680.77
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   17.9674(7)
_cell_length_b                   10.3025(4)
_cell_length_c                   9.3723(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1734.91(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2959
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.4780
_cell_measurement_theta_min      4.7070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.817
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9822
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.472
_diffrn_reflns_theta_min         4.718
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    146.00 172.00   1.00    8.00    --  110.57  15.00  60.00   26
  2  ω      5.00  58.00   1.00    3.00    --   40.45 -99.00  60.00   53
  3  ω    -76.00  29.00   1.00    3.00    --  -40.45  85.00 -55.00  105
  4  ω   -119.00 -10.00   1.00    3.00    --  -40.45 -77.00 120.00  109
  5  ω   -115.00 -24.00   1.00    3.00    --  -40.45 -77.00-150.00   91
  6  ω     81.00 161.00   1.00    8.00    --  110.57  30.00  90.00   80
  7  ω     62.00 144.00   1.00    8.00    --  110.57 -77.00 -60.00   82
  8  ω     58.00 129.00   1.00    8.00    --  110.57  15.00  60.00   71
  9  ω     45.00 115.00   1.00    8.00    --  110.57-111.00-120.00   70
 10  ω     36.00 139.00   1.00    8.00    --  110.57 -30.00-120.00  103
 11  ω     36.00 109.00   1.00    8.00    --  110.57 -61.00-150.00   73
 12  ω     33.00 129.00   1.00    8.00    --  110.57 -30.00  90.00   96
 13  ω     28.00 108.00   1.00    8.00    --  110.57 -94.00 120.00   80
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0416687000
_diffrn_orient_matrix_UB_12      -0.0565001000
_diffrn_orient_matrix_UB_13      0.1293201000
_diffrn_orient_matrix_UB_21      -0.0218932000
_diffrn_orient_matrix_UB_22      -0.1198652000
_diffrn_orient_matrix_UB_23      -0.0890678000
_diffrn_orient_matrix_UB_31      0.0716154000
_diffrn_orient_matrix_UB_32      -0.0695680000
_diffrn_orient_matrix_UB_33      0.0483789000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2825
_reflns_number_total             3114
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1031 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      1.001
_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)+(0.0583P)²+0.5968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1171
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6), C9(H9), C11(H11A), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C22(H22A,H22B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.27150(12) 0.5050(2) 0.1678(3) 0.0319(6) Uani 1 1 d . . . . .
O2 O 0.29715(12) 0.6404(2) 0.1587(3) 0.0341(6) Uani 1 1 d . . . . .
O3 O 0.42315(12) 0.5943(2) 0.1652(3) 0.0308(6) Uani 1 1 d . . . . .
O10 O 0.33224(14) 0.5779(2) 0.6080(3) 0.0357(6) Uani 1 1 d . . . . .
N11 N 0.39014(16) 0.5464(3) 0.3982(4) 0.0307(7) Uani 1 1 d . . . . .
H11 H 0.417(3) 0.606(4) 0.417(5) 0.043(13) Uiso 1 1 d . . . . .
C1 C 0.33228(18) 0.4166(3) 0.2053(4) 0.0297(8) Uani 1 1 d . . . . .
C2 C 0.40045(18) 0.4921(3) 0.2574(4) 0.0294(8) Uani 1 1 d . . . . .
H2 H 0.4427 0.4292 0.2635 0.035 Uiso 1 1 calc R . . . .
C3 C 0.36361(18) 0.6424(3) 0.0779(4) 0.0322(8) Uani 1 1 d . . . . .
C4 C 0.3581(2) 0.5634(3) -0.0590(4) 0.0373(9) Uani 1 1 d . . . . .
H4A H 0.3870 0.6080 -0.1344 0.045 Uiso 1 1 calc R . . . .
H4B H 0.3054 0.5614 -0.0899 0.045 Uiso 1 1 calc R . . . .
C5 C 0.3863(2) 0.4231(4) -0.0462(5) 0.0395(9) Uani 1 1 d . . . . .
H5A H 0.3787 0.3796 -0.1393 0.047 Uiso 1 1 calc R . . . .
H5B H 0.4406 0.4258 -0.0284 0.047 Uiso 1 1 calc R . . . .
C6 C 0.39844(18) 0.2186(3) 0.1029(5) 0.0391(10) Uani 1 1 d . . . . .
H6 H 0.4488 0.2496 0.1329 0.047 Uiso 1 1 calc R . . . .
C7 C 0.3660(2) 0.1388(3) 0.2252(5) 0.0405(10) Uani 1 1 d . . . . .
H7A H 0.3185 0.0994 0.1937 0.049 Uiso 1 1 calc R . . . .
H7B H 0.4007 0.0674 0.2488 0.049 Uiso 1 1 calc R . . . .
C8 C 0.35186(18) 0.2193(3) 0.3589(5) 0.0376(9) Uani 1 1 d . . . . .
H8A H 0.3997 0.2526 0.3962 0.045 Uiso 1 1 calc R . . . .
H8B H 0.3291 0.1639 0.4333 0.045 Uiso 1 1 calc R . . . .
C9 C 0.27873(19) 0.4179(3) 0.4543(4) 0.0311(8) Uani 1 1 d . . . . .
H9 H 0.2335 0.4675 0.4245 0.037 Uiso 1 1 calc R . . . .
C10 C 0.33649(19) 0.5189(3) 0.4929(4) 0.0296(7) Uani 1 1 d . . . . .
C11 C 0.35040(18) 0.3388(3) 0.0699(5) 0.0332(8) Uani 1 1 d . . . . .
H11A H 0.3021 0.3065 0.0308 0.040 Uiso 1 1 calc R . . . .
C12 C 0.30006(18) 0.3332(3) 0.3256(4) 0.0295(8) Uani 1 1 d . . . . .
H12 H 0.2527 0.2949 0.2884 0.035 Uiso 1 1 calc R . . . .
C13 C 0.3783(2) 0.7860(3) 0.0531(5) 0.0373(9) Uani 1 1 d . . . . .
H13A H 0.3759 0.8324 0.1443 0.056 Uiso 1 1 calc GR . . . .
H13B H 0.3407 0.8211 -0.0121 0.056 Uiso 1 1 calc GR . . . .
H13C H 0.4279 0.7972 0.0112 0.056 Uiso 1 1 calc GR . . . .
C14 C 0.4083(2) 0.1345(4) -0.0308(5) 0.0468(11) Uani 1 1 d . . . . .
H14A H 0.3593 0.1094 -0.0677 0.070 Uiso 1 1 calc GR . . . .
H14B H 0.4367 0.0564 -0.0064 0.070 Uiso 1 1 calc GR . . . .
H14C H 0.4352 0.1839 -0.1038 0.070 Uiso 1 1 calc GR . . . .
C15 C 0.2560(2) 0.3418(3) 0.5872(5) 0.0412(9) Uani 1 1 d . . . . .
H15A H 0.2181 0.2775 0.5616 0.062 Uiso 1 1 calc GR . . . .
H15B H 0.2357 0.4016 0.6586 0.062 Uiso 1 1 calc GR . . . .
H15C H 0.2997 0.2974 0.6267 0.062 Uiso 1 1 calc GR . . . .
O21 O 0.47085(17) 0.7785(3) 0.4887(4) 0.0604(10) Uani 1 1 d . . . . .
O22 O 0.38899(14) 0.8023(2) 0.6659(3) 0.0393(6) Uani 1 1 d . . . . .
H22 H 0.374(3) 0.712(6) 0.642(6) 0.086(19) Uiso 1 1 d . . . . .
C21 C 0.4414(2) 0.8445(3) 0.5801(5) 0.0384(9) Uani 1 1 d . . . . .
C22 C 0.4595(2) 0.9863(4) 0.6004(6) 0.0522(12) Uani 1 1 d . . . . .
H22A H 0.4356 1.0369 0.5231 0.063 Uiso 1 1 calc R . . . .
H22B H 0.4380 1.0159 0.6921 0.063 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 O2 1.472(3) . ?
O1 C1 1.465(4) . ?
O2 C3 1.414(4) . ?
O3 C2 1.422(4) . ?
O3 C3 1.435(4) . ?
O10 C10 1.240(4) . ?
N11 C2 1.444(5) . ?
N11 C10 1.341(5) . ?
C1 C2 1.531(4) . ?
C1 C11 1.536(5) . ?
C1 C12 1.531(5) . ?
C3 C4 1.523(5) . ?
C3 C13 1.521(4) . ?
C4 C5 1.537(5) . ?
C5 C11 1.535(6) . ?
C6 C7 1.527(6) . ?
C6 C11 1.541(5) . ?
C6 C14 1.533(6) . ?
C7 C8 1.523(6) . ?
C8 C12 1.530(4) . ?
C9 C10 1.513(4) . ?
C9 C12 1.538(5) . ?
C9 C15 1.527(5) . ?
O21 C21 1.214(5) . ?
O22 C21 1.312(5) . ?
C21 C22 1.509(5) . ?
C22 C22 1.484(8) 2_675 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 O2 111.7(2) . . ?
C3 O2 O1 108.0(2) . . ?
C2 O3 C3 112.9(2) . . ?
C10 N11 C2 127.9(3) . . ?
O1 C1 C2 110.9(2) . . ?
O1 C1 C11 106.5(3) . . ?
O1 C1 C12 104.1(3) . . ?
C2 C1 C11 111.1(3) . . ?
C12 C1 C2 110.7(3) . . ?
C12 C1 C11 113.3(3) . . ?
O3 C2 N11 107.8(2) . . ?
O3 C2 C1 114.3(3) . . ?
N11 C2 C1 112.7(3) . . ?
O2 C3 O3 108.6(3) . . ?
O2 C3 C4 112.9(3) . . ?
O2 C3 C13 104.1(3) . . ?
O3 C3 C4 110.1(3) . . ?
O3 C3 C13 107.1(3) . . ?
C13 C3 C4 113.8(3) . . ?
C3 C4 C5 114.6(3) . . ?
C11 C5 C4 116.7(3) . . ?
C7 C6 C11 111.6(3) . . ?
C7 C6 C14 110.7(3) . . ?
C14 C6 C11 110.8(4) . . ?
C8 C7 C6 112.9(3) . . ?
C7 C8 C12 110.5(3) . . ?
C10 C9 C12 114.0(3) . . ?
C10 C9 C15 110.0(3) . . ?
C15 C9 C12 114.5(3) . . ?
O10 C10 N11 121.1(3) . . ?
O10 C10 C9 120.2(3) . . ?
N11 C10 C9 118.7(3) . . ?
C1 C11 C6 111.9(3) . . ?
C5 C11 C1 112.3(3) . . ?
C5 C11 C6 111.2(3) . . ?
C1 C12 C9 110.7(3) . . ?
C8 C12 C1 110.5(3) . . ?
C8 C12 C9 115.3(3) . . ?
O21 C21 O22 124.1(3) . . ?
O21 C21 C22 122.5(4) . . ?
O22 C21 C22 113.4(3) . . ?
C22 C22 C21 113.3(4) 2_675 . ?

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
N11 H11 O21 0.80(5) 2.13(5) 2.923(4) 170(5) .
O22 H22 O10 0.99(6) 1.61(6) 2.585(3) 167(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 O2 C3 O3 -75.5(3) . . . . ?
O1 O2 C3 C4 46.9(4) . . . . ?
O1 O2 C3 C13 170.7(3) . . . . ?
O1 C1 C2 O3 -50.7(4) . . . . ?
O1 C1 C2 N11 72.8(4) . . . . ?
O1 C1 C11 C5 69.1(3) . . . . ?
O1 C1 C11 C6 -165.1(2) . . . . ?
O1 C1 C12 C8 169.8(3) . . . . ?
O1 C1 C12 C9 -61.2(3) . . . . ?
O2 O1 C1 C2 12.9(4) . . . . ?
O2 O1 C1 C11 -108.0(3) . . . . ?
O2 O1 C1 C12 132.0(3) . . . . ?
O2 C3 C4 C5 -94.2(4) . . . . ?
O3 C3 C4 C5 27.3(4) . . . . ?
C1 O1 O2 C3 46.7(4) . . . . ?
C2 O3 C3 O2 36.4(4) . . . . ?
C2 O3 C3 C4 -87.6(3) . . . . ?
C2 O3 C3 C13 148.2(3) . . . . ?
C2 N11 C10 O10 -176.4(3) . . . . ?
C2 N11 C10 C9 1.0(5) . . . . ?
C2 C1 C11 C5 -51.8(4) . . . . ?
C2 C1 C11 C6 74.1(3) . . . . ?
C2 C1 C12 C8 -71.0(4) . . . . ?
C2 C1 C12 C9 58.0(3) . . . . ?
C3 O3 C2 N11 -101.3(3) . . . . ?
C3 O3 C2 C1 24.8(4) . . . . ?
C3 C4 C5 C11 56.0(4) . . . . ?
C4 C5 C11 C1 -36.2(4) . . . . ?
C4 C5 C11 C6 -162.4(3) . . . . ?
C6 C7 C8 C12 57.0(4) . . . . ?
C7 C6 C11 C1 49.7(4) . . . . ?
C7 C6 C11 C5 176.1(3) . . . . ?
C7 C8 C12 C1 -56.4(4) . . . . ?
C7 C8 C12 C9 177.2(3) . . . . ?
C10 N11 C2 O3 140.3(3) . . . . ?
C10 N11 C2 C1 13.2(4) . . . . ?
C10 C9 C12 C1 -44.2(4) . . . . ?
C10 C9 C12 C8 82.2(3) . . . . ?
C11 C1 C2 O3 67.5(3) . . . . ?
C11 C1 C2 N11 -169.0(3) . . . . ?
C11 C1 C12 C8 54.5(4) . . . . ?
C11 C1 C12 C9 -176.5(3) . . . . ?
C11 C6 C7 C8 -53.5(4) . . . . ?
C12 C1 C2 O3 -165.7(3) . . . . ?
C12 C1 C2 N11 -42.2(3) . . . . ?
C12 C1 C11 C5 -177.0(3) . . . . ?
C12 C1 C11 C6 -51.2(4) . . . . ?
C12 C9 C10 O10 -167.6(3) . . . . ?
C12 C9 C10 N11 15.0(4) . . . . ?
C13 C3 C4 C5 147.5(3) . . . . ?
C14 C6 C7 C8 -177.5(3) . . . . ?
C14 C6 C11 C1 173.6(3) . . . . ?
C14 C6 C11 C5 -60.0(4) . . . . ?
C15 C9 C10 O10 -37.4(4) . . . . ?
C15 C9 C10 N11 145.2(3) . . . . ?
C15 C9 C12 C1 -172.0(3) . . . . ?
C15 C9 C12 C8 -45.7(4) . . . . ?
O21 C21 C22 C22 -46.5(5) . . . 2_675 ?
O22 C21 C22 C22 136.4(3) . . . 2_675 ?

_olex2_date_sample_data_collection 2017-06-27
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.240
_oxdiff_exptl_absorpt_empirical_full_min 0.859
####################################################################### 
# 
# 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_cpd4_madiha27cult
_database_code_depnum_ccdc_archive 'CCDC 1569111'
_audit_update_record             
;
2017-08-15 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2017-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            11-Aza:D-Man
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H23 N O4, C8 H8 O3'
_chemical_formula_sum            'C23 H31 N O7'
_chemical_formula_weight         433.49
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   10.00907(10)
_cell_length_b                   10.09992(10)
_cell_length_c                   20.9254(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2115.37(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9723
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.5490
_cell_measurement_theta_min      4.2190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless

_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12213
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.500
_diffrn_reflns_theta_min         4.226
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     40.00 130.00   1.00    3.00    --  110.57 -45.00-150.00   90
  2  ω     21.00  48.00   1.00    1.00    --   40.57 -99.00   0.00   27
  3  ω     88.00 178.00   1.00    3.00    --  110.57  45.00  30.00   90
  4  ω     93.00 178.00   1.00    3.00    --  110.57  45.00 150.00   85
  5  ω     97.00 178.00   1.00    3.00    --  110.57 125.00 -30.00   81
  6  ω    -94.00  -5.00   1.00    1.00    --  -40.57 125.00-120.00   89
  7  ω   -104.00 -17.00   1.00    1.00    --  -40.57 -37.00  30.00   87
  8  ω    -67.00  36.00   1.00    1.00    --  -40.57  37.00-150.00  103
  9  ω     96.00 178.00   1.00    3.00    --  110.57  82.00 -96.00   82
 10  ω     57.00 144.00   1.00    3.00    --  110.57 -77.00 -60.00   87
 11  ω     32.00  84.00   1.00    3.00    --  110.57-111.00-150.00   52
 12  ω    104.00 147.00   1.00    3.00    --  110.57 111.00-150.00   43
 13  ω     47.00 115.00   1.00    3.00    --  110.57-111.00 -90.00   68
 14  ω     33.00 112.00   1.00    3.00    --  110.57-111.00 120.00   79
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0917488000
_diffrn_orient_matrix_UB_12      -0.0045249000
_diffrn_orient_matrix_UB_13      0.0590989000
_diffrn_orient_matrix_UB_21      0.0749120000
_diffrn_orient_matrix_UB_22      -0.1233285000
_diffrn_orient_matrix_UB_23      0.0243883000
_diffrn_orient_matrix_UB_31      0.0983599000
_diffrn_orient_matrix_UB_32      0.0895369000
_diffrn_orient_matrix_UB_33      0.0365218000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                3677
_reflns_number_total             3723
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 
;
 Flack x determined using 1564 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3723
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0227
_refine_ls_restrained_S_all      1.000
_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)+(0.0360P)²+0.2670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0573
_refine_ls_wR_factor_ref         0.0576
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6), C9(H9), C11(H11A), C12(H12), C22(H22A)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.31757(10) 0.69046(11) 0.05058(5) 0.0159(2) Uani 1 1 d . . . . .
O2 O 0.17401(11) 0.66120(11) 0.05767(5) 0.0174(2) Uani 1 1 d . . . . .
O3 O 0.15908(10) 0.73110(10) 0.16224(5) 0.0153(2) Uani 1 1 d . . . . .
O10 O 0.34395(11) 0.33018(10) 0.16316(6) 0.0207(2) Uani 1 1 d . . . . .
N11 N 0.28973(12) 0.54268(13) 0.17843(6) 0.0147(3) Uani 1 1 d . . . . .
H11 H 0.232(2) 0.516(2) 0.2058(9) 0.018 Uiso 1 1 d R . . . .
C1 C 0.38200(14) 0.72254(14) 0.11142(7) 0.0130(3) Uani 1 1 d . . . . .
C2 C 0.29300(14) 0.68502(14) 0.16787(7) 0.0135(3) Uani 1 1 d . . . . .
H2 H 0.3322 0.7266 0.2070 0.016 Uiso 1 1 calc R . . . .
C3 C 0.11811(15) 0.75971(16) 0.09797(7) 0.0170(3) Uani 1 1 d . . . . .
C4 C 0.16040(15) 0.89982(16) 0.07844(8) 0.0190(3) Uani 1 1 d . . . . .
H4A H 0.0837 0.9603 0.0847 0.023 Uiso 1 1 calc R . . . .
H4B H 0.1824 0.8997 0.0323 0.023 Uiso 1 1 calc R . . . .
C5 C 0.28050(15) 0.95428(15) 0.11553(8) 0.0178(3) Uani 1 1 d . . . . .
H5A H 0.2551 0.9619 0.1611 0.021 Uiso 1 1 calc R . . . .
H5B H 0.2996 1.0448 0.0998 0.021 Uiso 1 1 calc R . . . .
C6 C 0.50949(15) 0.91304(15) 0.16427(7) 0.0159(3) Uani 1 1 d . . . . .
H6 H 0.4649 0.8994 0.2065 0.019 Uiso 1 1 calc R . . . .
C7 C 0.63440(16) 0.82650(15) 0.16228(8) 0.0185(3) Uani 1 1 d . . . . .
H7A H 0.6835 0.8441 0.1221 0.022 Uiso 1 1 calc R . . . .
H7B H 0.6935 0.8509 0.1983 0.022 Uiso 1 1 calc R . . . .
C8 C 0.60236(15) 0.67955(15) 0.16627(8) 0.0182(3) Uani 1 1 d . . . . .
H8A H 0.5582 0.6601 0.2075 0.022 Uiso 1 1 calc R . . . .
H8B H 0.6861 0.6276 0.1642 0.022 Uiso 1 1 calc R . . . .
C9 C 0.47696(15) 0.49098(14) 0.10689(8) 0.0164(3) Uani 1 1 d . . . . .
H9 H 0.4423 0.4757 0.0627 0.020 Uiso 1 1 calc R . . . .
C10 C 0.36623(15) 0.44813(15) 0.15197(7) 0.0159(3) Uani 1 1 d . . . . .
C11 C 0.40997(14) 0.87246(14) 0.11128(7) 0.0144(3) Uani 1 1 d . . . . .
H11A H 0.4528 0.8941 0.0694 0.017 Uiso 1 1 calc R . . . .
C12 C 0.51013(14) 0.63941(14) 0.11104(7) 0.0141(3) Uani 1 1 d . . . . .
H12 H 0.5585 0.6624 0.0707 0.017 Uiso 1 1 calc R . . . .
C13 C -0.03157(15) 0.73735(17) 0.09542(8) 0.0215(3) Uani 1 1 d . . . . .
H13A H -0.0507 0.6431 0.1017 0.032 Uiso 1 1 calc GR . . . .
H13B H -0.0658 0.7656 0.0537 0.032 Uiso 1 1 calc GR . . . .
H13C H -0.0750 0.7889 0.1292 0.032 Uiso 1 1 calc GR . . . .
C14 C 0.54737(16) 1.05892(15) 0.15877(8) 0.0195(3) Uani 1 1 d . . . . .
H14A H 0.5836 1.0763 0.1161 0.029 Uiso 1 1 calc GR . . . .
H14B H 0.6150 1.0804 0.1910 0.029 Uiso 1 1 calc GR . . . .
H14C H 0.4679 1.1138 0.1657 0.029 Uiso 1 1 calc GR . . . .
C15 C 0.59988(16) 0.40246(16) 0.11385(9) 0.0224(3) Uani 1 1 d . . . . .
H15A H 0.6329 0.4071 0.1579 0.034 Uiso 1 1 calc GR . . . .
H15B H 0.6698 0.4327 0.0845 0.034 Uiso 1 1 calc GR . . . .
H15C H 0.5758 0.3108 0.1036 0.034 Uiso 1 1 calc GR . . . .
O20 O 0.08230(10) 0.45553(11) 0.26313(5) 0.0163(2) Uani 1 1 d . . . . .
O21 O -0.12813(11) 0.45893(11) 0.22746(5) 0.0172(2) Uani 1 1 d . . . . .
H21 H -0.128(2) 0.532(2) 0.2462(10) 0.026 Uiso 1 1 d R . . . .
O22 O 0.12396(11) 0.20465(10) 0.21968(5) 0.0154(2) Uani 1 1 d . . . . .
H22 H 0.181(2) 0.244(2) 0.2032(10) 0.023 Uiso 1 1 d R . . . .
C21 C -0.01026(14) 0.40268(15) 0.23528(6) 0.0131(3) Uani 1 1 d . . . . .
C22 C -0.00169(14) 0.26435(14) 0.20568(7) 0.0140(3) Uani 1 1 d . . . . .
H22A H -0.0716 0.2091 0.2270 0.017 Uiso 1 1 calc R . . . .
C23 C -0.03421(14) 0.26578(14) 0.13498(7) 0.0148(3) Uani 1 1 d . . . . .
C24 C 0.01804(17) 0.36193(16) 0.09428(8) 0.0201(3) Uani 1 1 d . . . . .
H24 H 0.0765 0.4278 0.1107 0.024 Uiso 1 1 calc R . . . .
C25 C -0.01481(18) 0.36199(16) 0.02994(8) 0.0231(3) Uani 1 1 d . . . . .
H25 H 0.0206 0.4283 0.0026 0.028 Uiso 1 1 calc R . . . .
C26 C -0.09923(17) 0.26547(18) 0.00530(8) 0.0237(4) Uani 1 1 d . . . . .
H26 H -0.1224 0.2662 -0.0387 0.028 Uiso 1 1 calc R . . . .
C27 C -0.14954(17) 0.16796(16) 0.04538(8) 0.0219(3) Uani 1 1 d . . . . .
H27 H -0.2064 0.1011 0.0286 0.026 Uiso 1 1 calc R . . . .
C28 C -0.11684(15) 0.16788(15) 0.10999(8) 0.0177(3) Uani 1 1 d . . . . .
H28 H -0.1511 0.1006 0.1372 0.021 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 O2 1.4744(14) . ?
O1 C1 1.4635(18) . ?
O2 C3 1.4192(19) . ?
O3 C2 1.4238(18) . ?
O3 C3 1.4354(18) . ?
O10 C10 1.234(2) . ?
N11 C2 1.4549(19) . ?
N11 C10 1.343(2) . ?
C1 C2 1.527(2) . ?
C1 C11 1.5399(19) . ?
C1 C12 1.533(2) . ?
C3 C4 1.533(2) . ?
C3 C13 1.516(2) . ?
C4 C5 1.533(2) . ?
C5 C11 1.540(2) . ?
C6 C7 1.526(2) . ?
C6 C11 1.546(2) . ?
C6 C14 1.526(2) . ?
C7 C8 1.521(2) . ?
C8 C12 1.534(2) . ?
C9 C10 1.518(2) . ?
C9 C12 1.538(2) . ?
C9 C15 1.528(2) . ?
O20 C21 1.2177(19) . ?
O21 C21 1.3197(18) . ?
O22 C22 1.4252(17) . ?
C21 C22 1.531(2) . ?
C22 C23 1.515(2) . ?
C23 C24 1.393(2) . ?
C23 C28 1.391(2) . ?
C24 C25 1.386(2) . ?
C25 C26 1.389(3) . ?
C26 C27 1.388(3) . ?
C27 C28 1.391(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 O2 112.72(10) . . ?
C3 O2 O1 107.67(10) . . ?
C2 O3 C3 114.35(11) . . ?
C10 N11 C2 128.83(13) . . ?
O1 C1 C2 111.16(11) . . ?
O1 C1 C11 107.22(11) . . ?
O1 C1 C12 104.06(11) . . ?
C2 C1 C11 110.58(12) . . ?
C2 C1 C12 110.86(12) . . ?
C12 C1 C11 112.73(12) . . ?
O3 C2 N11 108.33(12) . . ?
O3 C2 C1 113.83(12) . . ?
N11 C2 C1 112.07(12) . . ?
O2 C3 O3 107.64(11) . . ?
O2 C3 C4 112.33(13) . . ?
O2 C3 C13 105.32(12) . . ?
O3 C3 C4 110.90(12) . . ?
O3 C3 C13 106.58(12) . . ?
C13 C3 C4 113.65(13) . . ?
C3 C4 C5 114.39(13) . . ?
C4 C5 C11 115.99(13) . . ?
C7 C6 C11 110.89(12) . . ?
C14 C6 C7 110.33(12) . . ?
C14 C6 C11 111.22(12) . . ?
C8 C7 C6 112.63(13) . . ?
C7 C8 C12 110.10(12) . . ?
C10 C9 C12 113.59(12) . . ?
C10 C9 C15 111.21(13) . . ?
C15 C9 C12 113.03(13) . . ?
O10 C10 N11 120.32(14) . . ?
O10 C10 C9 121.65(14) . . ?
N11 C10 C9 118.00(13) . . ?
C1 C11 C6 112.11(12) . . ?
C5 C11 C1 112.00(12) . . ?
C5 C11 C6 111.02(12) . . ?
C1 C12 C8 110.79(12) . . ?
C1 C12 C9 110.71(12) . . ?
C8 C12 C9 115.48(13) . . ?
O20 C21 O21 123.42(14) . . ?
O20 C21 C22 123.45(13) . . ?
O21 C21 C22 113.13(12) . . ?
O22 C22 C21 110.63(11) . . ?
O22 C22 C23 113.23(12) . . ?
C23 C22 C21 111.99(12) . . ?
C24 C23 C22 121.52(14) . . ?
C28 C23 C22 119.21(14) . . ?
C28 C23 C24 119.26(14) . . ?
C25 C24 C23 120.32(15) . . ?
C24 C25 C26 120.30(16) . . ?
C27 C26 C25 119.62(15) . . ?
C26 C27 C28 120.15(15) . . ?
C27 C28 C23 120.32(15) . . ?

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
N11 H11 O20 0.86(2) 2.02(2) 2.8682(17) 174.1(18) .
O21 H21 O22 0.83(2) 1.89(2) 2.7174(16) 174(2) 4
O22 H22 O10 0.77(2) 2.03(2) 2.8025(16) 174(2) .

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 O2 C3 O3 -74.95(13) . . . . ?
O1 O2 C3 C4 47.41(14) . . . . ?
O1 O2 C3 C13 171.62(11) . . . . ?
O1 C1 C2 O3 -48.94(15) . . . . ?
O1 C1 C2 N11 74.42(15) . . . . ?
O1 C1 C11 C5 69.32(15) . . . . ?
O1 C1 C11 C6 -165.11(11) . . . . ?
O1 C1 C12 C8 169.98(11) . . . . ?
O1 C1 C12 C9 -60.56(14) . . . . ?
O2 O1 C1 C2 13.80(15) . . . . ?
O2 O1 C1 C11 -107.17(12) . . . . ?
O2 O1 C1 C12 133.18(11) . . . . ?
O2 C3 C4 C5 -95.88(15) . . . . ?
O3 C3 C4 C5 24.61(18) . . . . ?
C1 O1 O2 C3 45.54(14) . . . . ?
C2 O3 C3 O2 38.86(15) . . . . ?
C2 O3 C3 C4 -84.38(14) . . . . ?
C2 O3 C3 C13 151.44(12) . . . . ?
C2 N11 C10 O10 -175.07(15) . . . . ?
C2 N11 C10 C9 3.2(2) . . . . ?
C2 C1 C11 C5 -52.01(16) . . . . ?
C2 C1 C11 C6 73.56(15) . . . . ?
C2 C1 C12 C8 -70.44(15) . . . . ?
C2 C1 C12 C9 59.02(16) . . . . ?
C3 O3 C2 N11 -103.72(13) . . . . ?
C3 O3 C2 C1 21.66(16) . . . . ?
C3 C4 C5 C11 58.43(18) . . . . ?
C4 C5 C11 C1 -37.79(18) . . . . ?
C4 C5 C11 C6 -163.96(12) . . . . ?
C6 C7 C8 C12 58.46(17) . . . . ?
C7 C6 C11 C1 50.69(16) . . . . ?
C7 C6 C11 C5 176.80(12) . . . . ?
C7 C8 C12 C1 -56.87(16) . . . . ?
C7 C8 C12 C9 176.26(13) . . . . ?
C10 N11 C2 O3 136.64(15) . . . . ?
C10 N11 C2 C1 10.2(2) . . . . ?
C10 C9 C12 C1 -45.64(17) . . . . ?
C10 C9 C12 C8 81.27(16) . . . . ?
C11 C1 C2 O3 70.03(15) . . . . ?
C11 C1 C2 N11 -166.60(12) . . . . ?
C11 C1 C12 C8 54.14(16) . . . . ?
C11 C1 C12 C9 -176.40(12) . . . . ?
C11 C6 C7 C8 -55.18(17) . . . . ?
C12 C1 C2 O3 -164.17(11) . . . . ?
C12 C1 C2 N11 -40.81(16) . . . . ?
C12 C1 C11 C5 -176.75(12) . . . . ?
C12 C1 C11 C6 -51.18(16) . . . . ?
C12 C9 C10 O10 -166.64(14) . . . . ?
C12 C9 C10 N11 15.1(2) . . . . ?
C13 C3 C4 C5 144.66(14) . . . . ?
C14 C6 C7 C8 -178.86(13) . . . . ?
C14 C6 C11 C1 173.86(12) . . . . ?
C14 C6 C11 C5 -60.03(16) . . . . ?
C15 C9 C10 O10 -37.8(2) . . . . ?
C15 C9 C10 N11 143.98(14) . . . . ?
C15 C9 C12 C1 -173.56(13) . . . . ?
C15 C9 C12 C8 -46.66(18) . . . . ?
O20 C21 C22 O22 4.44(19) . . . . ?
O20 C21 C22 C23 -122.90(15) . . . . ?
O21 C21 C22 O22 -175.66(11) . . . . ?
O21 C21 C22 C23 57.00(16) . . . . ?
O22 C22 C23 C24 -81.42(17) . . . . ?
O22 C22 C23 C28 97.79(16) . . . . ?
C21 C22 C23 C24 44.52(19) . . . . ?
C21 C22 C23 C28 -136.27(14) . . . . ?
C22 C23 C24 C25 -179.11(14) . . . . ?
C22 C23 C28 C27 179.20(14) . . . . ?
C23 C24 C25 C26 -0.6(3) . . . . ?
C24 C23 C28 C27 -1.6(2) . . . . ?
C24 C25 C26 C27 -0.7(3) . . . . ?
C25 C26 C27 C28 0.8(2) . . . . ?
C26 C27 C28 C23 0.4(2) . . . . ?
C28 C23 C24 C25 1.7(2) . . . . ?

_olex2_date_sample_data_collection 2017-05-16
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.303
_oxdiff_exptl_absorpt_empirical_full_min 0.712
####################################################################### 
# 
# 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_cpd6_madiha16a
_database_code_depnum_ccdc_archive 'CCDC 1569113'
_audit_update_record             
;
2017-08-15 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2017-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            11-Aza:L-Mal
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C15 H23 N O4), C4 H6 O5'
_chemical_formula_sum            'C34 H52 N2 O13'
_chemical_formula_weight         696.77
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   17.7811(3)
_cell_length_b                   10.3174(2)
_cell_length_c                   9.49693(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1742.26(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3703
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.1850
_cell_measurement_theta_min      4.9790
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.848
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4942
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.415
_diffrn_reflns_theta_min         5.280
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     94.00 178.00   1.00    5.00    --  110.57  45.00   0.00   84
  2  ω     36.00 136.00   1.00    5.00    --  110.57 -61.00-150.00  100
  3  ω     33.00 108.00   1.00    5.00    --  110.57 -94.00  60.00   75
  4  ω     36.00 108.00   1.00    5.00    --  110.57-111.00  30.00   72
  5  ω     25.00  97.00   1.00    1.00    --   40.57-125.00  60.00   72
  6  ω   -114.00  -3.00   1.00    1.00    --  -40.57 -19.00 -30.00  111
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0718188000
_diffrn_orient_matrix_UB_12      -0.0820565000
_diffrn_orient_matrix_UB_13      -0.0169375000
_diffrn_orient_matrix_UB_21      0.0458874000
_diffrn_orient_matrix_UB_22      -0.1240724000
_diffrn_orient_matrix_UB_23      0.0275833000
_diffrn_orient_matrix_UB_31      -0.0156953000
_diffrn_orient_matrix_UB_32      0.0126916000
_diffrn_orient_matrix_UB_33      0.1589443000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                3011
_reflns_number_total             3094
_reflns_odcompleteness_completeness 99.20
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 
;
 Flack x determined using 1245 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3094
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0258
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0595P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0752
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O23-H23
 0.9 with sigma of 0.02
 O21-H21 = O23-H23
 0.9 with sigma of 0.05
 C22-C24 \\sim C21-C23
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 O20, O21, H21, O22, O23, H23, O24, C21, C22, C23, C24
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Fixed Sof: O20(0.5) O21(0.5) H21(0.5) O22(0.5) H22(0.5) O23(0.5) H23(0.5)
 O24(0.5) C21(0.5) C22(0.5) H22A(0.5) C23(0.5) H23A(0.5) H23B(0.5) C24(0.5)
5.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6), C9(H9), C11(H11A), C12(H12), C22(H22A)
5.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C23(H23A,H23B)
5.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.26900(6) 0.49818(11) 0.32547(12) 0.0231(3) Uani 1 1 d . . . . .
O2 O 0.29445(7) 0.36309(12) 0.33781(13) 0.0256(3) Uani 1 1 d . . . . .
O3 O 0.42192(7) 0.40801(12) 0.33343(12) 0.0216(3) Uani 1 1 d . . . . .
O10 O 0.33464(7) 0.42007(12) -0.10839(12) 0.0247(3) Uani 1 1 d . . . . .
N11 N 0.39029(8) 0.45170(14) 0.10093(14) 0.0196(3) Uani 1 1 d . . . . .
H11 H 0.4189(15) 0.390(3) 0.083(3) 0.032(6) Uiso 1 1 d . . . . .
C1 C 0.33082(9) 0.58460(17) 0.28812(16) 0.0200(3) Uani 1 1 d . . . . .
C2 C 0.40023(9) 0.50850(15) 0.23993(16) 0.0194(3) Uani 1 1 d . . . . .
H2 H 0.4431 0.5710 0.2339 0.023 Uiso 1 1 calc R . . . .
C3 C 0.36105(10) 0.36157(18) 0.41967(18) 0.0262(4) Uani 1 1 d . . . . .
C4 C 0.35469(12) 0.4435(2) 0.55291(18) 0.0342(4) Uani 1 1 d . . . . .
H4A H 0.3828 0.3998 0.6294 0.041 Uiso 1 1 calc R . . . .
H4B H 0.3012 0.4471 0.5814 0.041 Uiso 1 1 calc R . . . .
C5 C 0.38419(12) 0.5820(2) 0.53813(18) 0.0324(4) Uani 1 1 d . . . . .
H5A H 0.4391 0.5778 0.5213 0.039 Uiso 1 1 calc R . . . .
H5B H 0.3765 0.6271 0.6290 0.039 Uiso 1 1 calc R . . . .
C6 C 0.39808(10) 0.78395(18) 0.3873(2) 0.0322(4) Uani 1 1 d . . . . .
H6 H 0.4490 0.7519 0.3590 0.039 Uiso 1 1 calc R . . . .
C7 C 0.36590(11) 0.86202(18) 0.2649(2) 0.0338(4) Uani 1 1 d . . . . .
H7A H 0.4012 0.9330 0.2412 0.041 Uiso 1 1 calc R . . . .
H7B H 0.3178 0.9018 0.2946 0.041 Uiso 1 1 calc R . . . .
C8 C 0.35229(10) 0.77982(17) 0.1336(2) 0.0274(4) Uani 1 1 d . . . . .
H8A H 0.4008 0.7458 0.0983 0.033 Uiso 1 1 calc R . . . .
H8B H 0.3298 0.8343 0.0588 0.033 Uiso 1 1 calc R . . . .
C9 C 0.27873(9) 0.58059(16) 0.04071(16) 0.0211(3) Uani 1 1 d . . . . .
H9 H 0.2328 0.5313 0.0698 0.025 Uiso 1 1 calc R . . . .
C10 C 0.33777(9) 0.47948(15) 0.00592(16) 0.0194(3) Uani 1 1 d . . . . .
C11 C 0.34859(10) 0.66521(17) 0.42071(19) 0.0263(4) Uani 1 1 d . . . . .
H11A H 0.2996 0.6987 0.4577 0.032 Uiso 1 1 calc R . . . .
C12 C 0.29963(8) 0.66693(15) 0.16718(18) 0.0208(3) Uani 1 1 d . . . . .
H12 H 0.2516 0.7060 0.2020 0.025 Uiso 1 1 calc R . . . .
C13 C 0.37606(12) 0.2187(2) 0.44631(19) 0.0324(4) Uani 1 1 d . . . . .
H13A H 0.3727 0.1710 0.3573 0.049 Uiso 1 1 calc GR . . . .
H13B H 0.3386 0.1849 0.5125 0.049 Uiso 1 1 calc GR . . . .
H13C H 0.4265 0.2082 0.4863 0.049 Uiso 1 1 calc GR . . . .
C14 C 0.40755(13) 0.8695(2) 0.5183(3) 0.0452(6) Uani 1 1 d . . . . .
H14A H 0.4367 0.9469 0.4937 0.068 Uiso 1 1 calc GR . . . .
H14B H 0.4341 0.8208 0.5916 0.068 Uiso 1 1 calc GR . . . .
H14C H 0.3579 0.8955 0.5532 0.068 Uiso 1 1 calc GR . . . .
C15 C 0.25656(12) 0.65621(18) -0.09141(19) 0.0312(4) Uani 1 1 d . . . . .
H15A H 0.2180 0.7203 -0.0673 0.047 Uiso 1 1 calc GR . . . .
H15B H 0.2367 0.5962 -0.1622 0.047 Uiso 1 1 calc GR . . . .
H15C H 0.3009 0.7006 -0.1294 0.047 Uiso 1 1 calc GR . . . .
O20 O 0.4696(12) 0.2208(16) 0.022(2) 0.033(2) Uani 0.5 1 d . U P A -1
O21 O 0.3944(19) 0.198(2) -0.172(2) 0.031(4) Uani 0.5 1 d D U P A -1
H21 H 0.370(5) 0.274(7) -0.138(9) 0.03(2) Uiso 0.5 1 d D U P B -1
O22 O 0.39814(15) -0.0587(3) -0.1549(3) 0.0322(6) Uani 0.5 1 d . U P A -1
H22 H 0.382(5) -0.006(8) -0.218(9) 0.09(3) Uiso 0.5 1 d . . P C -1
O23 O 0.6062(18) -0.205(3) -0.163(2) 0.028(3) Uani 0.5 1 d D U P A -1
H23 H 0.619(6) -0.288(5) -0.141(13) 0.06(4) Uiso 0.5 1 d D U P D -1
O24 O 0.5377(12) -0.2081(16) 0.0265(19) 0.031(2) Uani 0.5 1 d . U P A -1
C21 C 0.4379(10) 0.1554(16) -0.0644(14) 0.0224(18) Uani 0.5 1 d D U P A -1
C22 C 0.4511(2) 0.0077(4) -0.0720(5) 0.0206(8) Uani 0.5 1 d D U P A -1
H22A H 0.4467 -0.0268 0.0261 0.025 Uiso 0.5 1 calc R . P A -1
C23 C 0.5310(3) -0.0187(4) -0.1213(5) 0.0238(9) Uani 0.5 1 d D U P A -1
H23A H 0.5338 -0.0072 -0.2246 0.029 Uiso 0.5 1 calc R . P A -1
H23B H 0.5655 0.0445 -0.0771 0.029 Uiso 0.5 1 calc R . P A -1
C24 C 0.5554(10) -0.1542(16) -0.0837(14) 0.025(2) Uani 0.5 1 d D U P A -1


_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 O2 1.4701(17) . ?
O1 C1 1.459(2) . ?
O2 C3 1.417(2) . ?
O3 C2 1.4186(19) . ?
O3 C3 1.439(2) . ?
O10 C10 1.248(2) . ?
N11 C2 1.455(2) . ?
N11 C10 1.330(2) . ?
C1 C2 1.533(2) . ?
C1 C11 1.542(2) . ?
C1 C12 1.532(2) . ?
C3 C4 1.526(2) . ?
C3 C13 1.519(3) . ?
C4 C5 1.529(3) . ?
C5 C11 1.543(3) . ?
C6 C7 1.526(3) . ?
C6 C11 1.541(3) . ?
C6 C14 1.535(3) . ?
C7 C8 1.527(3) . ?
C8 C12 1.528(2) . ?
C9 C10 1.516(2) . ?
C9 C12 1.541(2) . ?
C9 C15 1.529(2) . ?
O20 C21 1.205(17) . ?
O21 C21 1.36(2) . ?
O22 C22 1.405(5) . ?
O23 C24 1.29(3) . ?
O24 C24 1.226(16) . ?
C21 C22 1.544(14) . ?
C22 C23 1.520(6) . ?
C23 C24 1.507(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 O2 111.52(11) . . ?
C3 O2 O1 108.16(12) . . ?
C2 O3 C3 113.27(12) . . ?
C10 N11 C2 127.88(14) . . ?
O1 C1 C2 111.48(13) . . ?
O1 C1 C11 106.59(13) . . ?
O1 C1 C12 104.38(12) . . ?
C2 C1 C11 110.80(13) . . ?
C12 C1 C2 110.58(13) . . ?
C12 C1 C11 112.78(14) . . ?
O3 C2 N11 107.85(12) . . ?
O3 C2 C1 113.98(13) . . ?
N11 C2 C1 112.30(12) . . ?
O2 C3 O3 108.22(13) . . ?
O2 C3 C4 112.77(15) . . ?
O2 C3 C13 104.42(15) . . ?
O3 C3 C4 110.08(15) . . ?
O3 C3 C13 106.60(15) . . ?
C13 C3 C4 114.34(15) . . ?
C3 C4 C5 114.59(15) . . ?
C4 C5 C11 116.47(16) . . ?
C7 C6 C11 111.25(15) . . ?
C7 C6 C14 110.80(16) . . ?
C14 C6 C11 110.66(18) . . ?
C6 C7 C8 112.85(15) . . ?
C7 C8 C12 110.48(15) . . ?
C10 C9 C12 113.61(13) . . ?
C10 C9 C15 110.53(13) . . ?
C15 C9 C12 114.00(14) . . ?
O10 C10 N11 121.05(15) . . ?
O10 C10 C9 119.77(14) . . ?
N11 C10 C9 119.12(14) . . ?
C1 C11 C5 111.97(14) . . ?
C6 C11 C1 112.18(15) . . ?
C6 C11 C5 110.91(15) . . ?
C1 C12 C9 110.55(13) . . ?
C8 C12 C1 110.93(13) . . ?
C8 C12 C9 115.19(14) . . ?
O20 C21 O21 127.0(19) . . ?
O20 C21 C22 120.9(12) . . ?
O21 C21 C22 111.8(14) . . ?
O22 C22 C21 113.9(6) . . ?
O22 C22 C23 111.4(3) . . ?
C23 C22 C21 109.5(8) . . ?
C24 C23 C22 111.3(7) . . ?
O23 C24 C23 116.1(14) . . ?
O24 C24 O23 119.8(15) . . ?
O24 C24 C23 123.3(13) . . ?

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
N11 H11 O20 0.83(3) 2.05(3) 2.868(18) 168(2) .
N11 H11 O24 0.83(3) 2.10(3) 2.908(18) 164(2) 2_655
O21 H21 O10 0.95(5) 1.66(5) 2.60(2) 168(9) .
O23 H23 O10 0.91(3) 1.62(5) 2.51(3) 164(11) 2_655

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 O2 C3 O3 -75.44(15) . . . . ?
O1 O2 C3 C4 46.57(17) . . . . ?
O1 O2 C3 C13 171.29(12) . . . . ?
O1 C1 C2 O3 -50.33(17) . . . . ?
O1 C1 C2 N11 72.70(16) . . . . ?
O1 C1 C11 C5 69.35(18) . . . . ?
O1 C1 C11 C6 -165.20(13) . . . . ?
O1 C1 C12 C8 169.43(13) . . . . ?
O1 C1 C12 C9 -61.51(15) . . . . ?
O2 O1 C1 C2 12.83(15) . . . . ?
O2 O1 C1 C11 -108.20(13) . . . . ?
O2 O1 C1 C12 132.23(12) . . . . ?
O2 C3 C4 C5 -94.44(19) . . . . ?
O3 C3 C4 C5 26.5(2) . . . . ?
C1 O1 O2 C3 46.91(15) . . . . ?
C2 O3 C3 O2 36.40(18) . . . . ?
C2 O3 C3 C4 -87.25(16) . . . . ?
C2 O3 C3 C13 148.22(13) . . . . ?
C2 N11 C10 O10 -177.92(15) . . . . ?
C2 N11 C10 C9 -0.9(2) . . . . ?
C2 C1 C11 C5 -52.11(19) . . . . ?
C2 C1 C11 C6 73.34(17) . . . . ?
C2 C1 C12 C8 -70.56(17) . . . . ?
C2 C1 C12 C9 58.49(17) . . . . ?
C3 O3 C2 N11 -101.19(15) . . . . ?
C3 O3 C2 C1 24.23(18) . . . . ?
C3 C4 C5 C11 56.7(2) . . . . ?
C4 C5 C11 C1 -36.6(2) . . . . ?
C4 C5 C11 C6 -162.76(15) . . . . ?
C6 C7 C8 C12 57.2(2) . . . . ?
C7 C6 C11 C1 50.31(19) . . . . ?
C7 C6 C11 C5 176.34(15) . . . . ?
C7 C8 C12 C1 -56.23(18) . . . . ?
C7 C8 C12 C9 177.24(14) . . . . ?
C10 N11 C2 O3 141.14(16) . . . . ?
C10 N11 C2 C1 14.7(2) . . . . ?
C10 C9 C12 C1 -44.76(18) . . . . ?
C10 C9 C12 C8 81.96(17) . . . . ?
C11 C1 C2 O3 68.21(17) . . . . ?
C11 C1 C2 N11 -168.76(14) . . . . ?
C11 C1 C12 C8 54.14(18) . . . . ?
C11 C1 C12 C9 -176.81(13) . . . . ?
C11 C6 C7 C8 -54.0(2) . . . . ?
C12 C1 C2 O3 -165.97(13) . . . . ?
C12 C1 C2 N11 -42.95(17) . . . . ?
C12 C1 C11 C5 -176.69(14) . . . . ?
C12 C1 C11 C6 -51.24(18) . . . . ?
C12 C9 C10 O10 -166.67(14) . . . . ?
C12 C9 C10 N11 16.2(2) . . . . ?
C13 C3 C4 C5 146.46(17) . . . . ?
C14 C6 C7 C8 -177.59(17) . . . . ?
C14 C6 C11 C1 173.94(15) . . . . ?
C14 C6 C11 C5 -60.03(19) . . . . ?
C15 C9 C10 O10 -37.1(2) . . . . ?
C15 C9 C10 N11 145.85(16) . . . . ?
C15 C9 C12 C1 -172.61(14) . . . . ?
C15 C9 C12 C8 -45.89(19) . . . . ?
O20 C21 C22 O22 166.1(18) . . . . ?
O20 C21 C22 C23 -68(2) . . . . ?
O21 C21 C22 O22 -20(2) . . . . ?
O21 C21 C22 C23 105(2) . . . . ?
O22 C22 C23 C24 -72.6(8) . . . . ?
C21 C22 C23 C24 160.4(8) . . . . ?
C22 C23 C24 O23 153(2) . . . . ?
C22 C23 C24 O24 -37(2) . . . . ?

_olex2_date_sample_data_collection 2017-05-16
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.269
_oxdiff_exptl_absorpt_empirical_full_min 0.770
####################################################################### 
# 
# 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_cpd8_madiha38cult
_database_code_depnum_ccdc_archive 'CCDC 1569115'
_audit_update_record             
;
2017-08-15 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2017-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            11-Aza:Pim
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C15 H23 N O4), C7 H12 O4'
_chemical_formula_sum            'C37 H58 N2 O12'
_chemical_formula_weight         722.85
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   17.5836(7)
_cell_length_b                   10.3594(4)
_cell_length_c                   9.9524(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1812.89(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5938
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      75.1850
_cell_measurement_theta_min      4.4360
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16856
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.486
_diffrn_reflns_theta_min         4.443
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     78.00 112.00   1.00    8.00    --  110.57  77.00 -90.00   34
  2  ω     12.00 113.00   1.00    3.00    --   40.45  57.00  30.00  101
  3  ω    121.00 178.00   1.00    8.00    --  110.57  77.00 -90.00   57
  4  ω    152.00 177.00   1.00    8.00    --  110.57  37.00 -66.21   25
  5  ω    142.00 169.00   1.00    8.00    --  110.57  61.00 -60.00   27
  6  ω    121.00 177.00   1.00    8.00    --  110.57  77.00 -30.00   56
  7  ω     85.00 112.00   1.00    8.00    --  110.57  45.00 -30.00   27
  8  ω     84.00 109.00   1.00    8.00    --  110.57  45.00   0.00   25
  9  ω     81.00 106.00   1.00    8.00    --  110.57  61.00 -30.00   25
 10  ω     85.00 111.00   1.00    8.00    --  110.57  30.00 -30.00   26
 11  ω     85.00 124.00   1.00    8.00    --  110.57  30.00   0.00   39
 12  ω     84.00 145.00   1.00    8.00    --  110.57  45.00  30.00   61
 13  ω     78.00 103.00   1.00    8.00    --  110.57  77.00   0.00   25
 14  ω     80.00 106.00   1.00    8.00    --  110.57  61.00   0.00   26
 15  ω     80.00 105.00   1.00    8.00    --  110.57  68.00  17.69   25
 16  ω     77.00 104.00   1.00    8.00    --  110.57  77.00 -30.00   27
 17  ω     78.00 103.00   1.00    8.00    --  110.57  77.00 -60.00   25
 18  ω     81.00 106.00   1.00    8.00    --  110.57  61.00 -90.00   25
 19  ω     84.00 121.00   1.00    8.00    --  110.57  37.00 -66.21   37
 20  ω     80.00 106.00   1.00    8.00    --  110.57  61.00-120.00   26
 21  ω     83.00 109.00   1.00    8.00    --  110.57  45.00 -90.00   26
 22  ω     83.00 110.00   1.00    8.00    --  110.57  45.00 -60.00   27
 23  ω     80.00 106.00   1.00    8.00    --  110.57  61.00 -60.00   26
 24  ω     77.00 103.00   1.00    8.00    --  110.57  77.00-120.00   26
 25  ω     78.00 173.00   1.00    8.00    --  110.57  77.00-150.00   95
 26  ω     81.00 106.00   1.00    8.00    --  110.57  30.00  30.00   25
 27  ω     80.00 107.00   1.00    8.00    --  110.57  61.00  30.00   27
 28  ω     78.00 105.00   1.00    8.00    --  110.57  77.00  30.00   27
 29  ω     77.00 177.00   1.00    8.00    --  110.57  77.00  60.00  100
 30  ω     48.00 106.00   1.00    8.00    --  110.57 -94.00  90.00   58
 31  ω     26.00 104.00   1.00    8.00    --  110.57 -94.00   0.00   78
 32  ω     97.00 122.00   1.00    8.00    --  110.57-125.00 -90.00   25
 33  ω     56.00  98.00   1.00    3.00    --   40.45-125.00-180.00   42
 34  ω     36.00  80.00   1.00    8.00    --  110.57-125.00 -90.00   44
 35  ω     15.00 100.00   1.00    3.00    --   40.45  37.00 -30.00   85
 36  ω     27.00  54.00   1.00    3.00    --   40.45  57.00-150.00   27
 37  ω      8.00  36.00   1.00    3.00    --   40.45  77.00 -60.00   28
 38  ω      9.00  34.00   1.00    3.00    --   40.45  77.00 -30.00   25
 39  ω    -45.00 -20.00   1.00    3.00    --  -40.45 -57.00  60.00   25
 40  ω   -100.00 -62.00   1.00    3.00    --  -40.45 -57.00  60.00   38
 41  ω    -66.00  32.00   1.00    3.00    --  -40.45  37.00-150.00   98
 42  ω   -110.00 -61.00   1.00    3.00    --  -40.45-155.00 148.00   49
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0850853000
_diffrn_orient_matrix_UB_12      -0.0157221000
_diffrn_orient_matrix_UB_13      -0.0334424000
_diffrn_orient_matrix_UB_21      0.0179023000
_diffrn_orient_matrix_UB_22      0.0130888000
_diffrn_orient_matrix_UB_23      -0.1508174000
_diffrn_orient_matrix_UB_31      0.0108382000
_diffrn_orient_matrix_UB_32      -0.1472813000
_diffrn_orient_matrix_UB_33      -0.0098907000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3057
_reflns_number_total             3259
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 1210 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3259
_refine_ls_number_restraints     55
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0312
_refine_ls_restrained_S_all      1.028
_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)+(0.0340P)²+0.2270P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0729
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C22-C21 \\sim C23-C22 \\sim C24-C23 \\sim C24-C25 \\sim C25-C26 \\sim C26-C27
 with sigma of 0.02
 C21-C23 \\sim C25-C27
 with sigma of 0.02
 C22-C24 \\sim C23-C25
 with sigma of 0.02
 C23-C25 \\sim C24-C26
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 O22, O23, C26, C27
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.001
 O20, O21, C21, C22
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.001
4. Others
 Fixed Sof: O20(0.5) O21(0.5) H21(0.5) O22(0.5) H22(0.5) O23(0.5) C21(0.5)
 C22(0.5) H22A(0.5) H22B(0.5) C23(0.5) H23A(0.5) H23B(0.5) C24(0.5) H24A(0.5)
 H24B(0.5) C25(0.5) H25A(0.5) H25B(0.5) C26(0.5) H26A(0.5) H26B(0.5) C27(0.5)
5.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6), C9(H9), C11(H11A), C12(H12)
5.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C22(H22A,H22B), C23(H23A,
 H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B)
5.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
5.d Idealised tetrahedral OH refined as rotating group:
 O21(H21), O22(H22)
;
_atom_sites_solution_hydrogens   mixed
_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 0.73477(8) 0.19475(15) 0.18857(15) 0.0284(3) Uani 1 1 d . . . . .
O2 O 0.70598(9) 0.06179(15) 0.17489(16) 0.0320(4) Uani 1 1 d . . . . .
O3 O 0.57863(9) 0.11629(16) 0.17804(17) 0.0348(4) Uani 1 1 d . . . . .
O10 O 0.66270(10) 0.13283(16) 0.60857(15) 0.0370(4) Uani 1 1 d . . . . .
N11 N 0.61270(11) 0.15360(19) 0.4016(2) 0.0300(4) Uani 1 1 d . . . . .
H11 H 0.5802(19) 0.095(3) 0.423(3) 0.056(10) Uiso 1 1 d . . . . .
C1 C 0.67425(12) 0.2846(2) 0.2242(2) 0.0249(4) Uani 1 1 d . . . . .
C2 C 0.60307(13) 0.2121(2) 0.2693(2) 0.0291(5) Uani 1 1 d . . . . .
H2 H 0.5611 0.2769 0.2769 0.035 Uiso 1 1 calc R . . . .
C3 C 0.63898(15) 0.0655(2) 0.0961(2) 0.0348(5) Uani 1 1 d . . . . .
C4 C 0.64911(18) 0.1474(3) -0.0307(2) 0.0421(6) Uani 1 1 d . . . . .
H4A H 0.7036 0.1472 -0.0558 0.051 Uiso 1 1 calc R . . . .
H4B H 0.6205 0.1065 -0.1050 0.051 Uiso 1 1 calc R . . . .
C5 C 0.62263(17) 0.2874(3) -0.0167(3) 0.0432(6) Uani 1 1 d . . . . .
H5A H 0.5668 0.2872 -0.0032 0.052 Uiso 1 1 calc R . . . .
H5B H 0.6329 0.3324 -0.1026 0.052 Uiso 1 1 calc R . . . .
C6 C 0.61113(15) 0.4879(2) 0.1295(3) 0.0406(6) Uani 1 1 d . . . . .
H6 H 0.5587 0.4586 0.1540 0.049 Uiso 1 1 calc R . . . .
C7 C 0.64336(14) 0.5628(2) 0.2494(3) 0.0361(6) Uani 1 1 d . . . . .
H7A H 0.6926 0.6018 0.2233 0.043 Uiso 1 1 calc R . . . .
H7B H 0.6081 0.6339 0.2726 0.043 Uiso 1 1 calc R . . . .
C8 C 0.65525(12) 0.4786(2) 0.3725(2) 0.0305(5) Uani 1 1 d . . . . .
H8A H 0.6055 0.4460 0.4046 0.037 Uiso 1 1 calc R . . . .
H8B H 0.6783 0.5306 0.4454 0.037 Uiso 1 1 calc R . . . .
C9 C 0.72660(12) 0.2780(2) 0.4599(2) 0.0247(4) Uani 1 1 d . . . . .
H9 H 0.7711 0.2245 0.4316 0.030 Uiso 1 1 calc R . . . .
C10 C 0.66414(13) 0.1839(2) 0.4954(2) 0.0274(5) Uani 1 1 d . . . . .
C11 C 0.65901(14) 0.3666(2) 0.0977(2) 0.0331(5) Uani 1 1 d . . . . .
H11A H 0.7095 0.3974 0.0643 0.040 Uiso 1 1 calc R . . . .
C12 C 0.70722(11) 0.3647(2) 0.3392(2) 0.0242(4) Uani 1 1 d . . . . .
H12 H 0.7563 0.4018 0.3062 0.029 Uiso 1 1 calc R . . . .
C13 C 0.61955(17) -0.0747(3) 0.0699(3) 0.0443(6) Uani 1 1 d . . . . .
H13A H 0.6549 -0.1102 0.0032 0.066 Uiso 1 1 calc GR . . . .
H13B H 0.5674 -0.0808 0.0357 0.066 Uiso 1 1 calc GR . . . .
H13C H 0.6238 -0.1237 0.1537 0.066 Uiso 1 1 calc GR . . . .
C14 C 0.60437(19) 0.5771(3) 0.0086(3) 0.0586(9) Uani 1 1 d . . . . .
H14A H 0.6550 0.6079 -0.0172 0.088 Uiso 1 1 calc GR . . . .
H14B H 0.5721 0.6509 0.0317 0.088 Uiso 1 1 calc GR . . . .
H14C H 0.5816 0.5298 -0.0667 0.088 Uiso 1 1 calc GR . . . .
C15 C 0.75242(13) 0.3527(2) 0.5846(2) 0.0318(5) Uani 1 1 d . . . . .
H15A H 0.7092 0.4004 0.6221 0.048 Uiso 1 1 calc GR . . . .
H15B H 0.7927 0.4135 0.5596 0.048 Uiso 1 1 calc GR . . . .
H15C H 0.7719 0.2921 0.6519 0.048 Uiso 1 1 calc GR . . . .
O20 O 0.5502(11) 0.8646(14) 0.4944(14) 0.0318(19) Uani 0.5 1 d . U P A -1
O21 O 0.5880(12) 0.9350(19) 0.6963(16) 0.0250(19) Uani 0.5 1 d . U P A -1
H21 H 0.5999 1.0008 0.6517 0.037 Uiso 0.5 1 calc GR . P A -1
O22 O 0.4025(12) 0.0653(18) 0.7141(16) 0.024(2) Uani 0.5 1 d . U P A -1
H22 H 0.3816 0.0029 0.6749 0.035 Uiso 0.5 1 calc GR . P A -1
O23 O 0.4441(12) 0.1147(15) 0.5088(14) 0.035(2) Uani 0.5 1 d . U P A -1
C21 C 0.5563(13) 0.8470(14) 0.614(2) 0.028(3) Uani 0.5 1 d D U P A -1
C22 C 0.5523(3) 0.7187(5) 0.6887(5) 0.0266(11) Uani 0.5 1 d D U P A -1
H22A H 0.5284 0.7326 0.7776 0.032 Uiso 0.5 1 calc R . P A -1
H22B H 0.6046 0.6866 0.7041 0.032 Uiso 0.5 1 calc R . P A -1
C23 C 0.5072(6) 0.6163(10) 0.6122(15) 0.026(2) Uani 0.5 1 d D . P A -1
H23A H 0.4526 0.6393 0.6133 0.031 Uiso 0.5 1 calc R . P A -1
H23B H 0.5242 0.6145 0.5174 0.031 Uiso 0.5 1 calc R . P A -1
C24 C 0.5176(2) 0.4836(5) 0.6736(4) 0.0238(11) Uani 0.5 1 d D . P A -1
H24A H 0.5051 0.4890 0.7704 0.029 Uiso 0.5 1 calc R . P A -1
H24B H 0.5719 0.4596 0.6663 0.029 Uiso 0.5 1 calc R . P A -1
C25 C 0.4703(6) 0.3759(9) 0.6117(14) 0.021(2) Uani 0.5 1 d D . P A -1
H25A H 0.4849 0.3644 0.5164 0.025 Uiso 0.5 1 calc R . P A -1
H25B H 0.4158 0.3997 0.6148 0.025 Uiso 0.5 1 calc R . P A -1
C26 C 0.4825(3) 0.2490(5) 0.6877(5) 0.0232(10) Uani 0.5 1 d D U P A -1
H26A H 0.4675 0.2606 0.7828 0.028 Uiso 0.5 1 calc R . P A -1
H26B H 0.5371 0.2259 0.6854 0.028 Uiso 0.5 1 calc R . P A -1
C27 C 0.4357(12) 0.1391(13) 0.6258(16) 0.019(2) Uani 0.5 1 d D U P A -1


_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 O2 1.474(2) . ?
O1 C1 1.457(3) . ?
O2 C3 1.416(3) . ?
O3 C2 1.412(3) . ?
O3 C3 1.438(3) . ?
O10 C10 1.245(3) . ?
N11 C2 1.459(3) . ?
N11 C10 1.337(3) . ?
C1 C2 1.527(3) . ?
C1 C11 1.543(3) . ?
C1 C12 1.528(3) . ?
C3 C4 1.531(3) . ?
C3 C13 1.515(3) . ?
C4 C5 1.530(4) . ?
C5 C11 1.542(3) . ?
C6 C7 1.532(3) . ?
C6 C11 1.545(4) . ?
C6 C14 1.522(4) . ?
C7 C8 1.519(3) . ?
C8 C12 1.529(3) . ?
C9 C10 1.511(3) . ?
C9 C12 1.538(3) . ?
C9 C15 1.531(3) . ?
O20 C21 1.213(19) . ?
O21 C21 1.344(16) . ?
O22 C27 1.303(15) . ?
O23 C27 1.200(17) . ?
C21 C22 1.523(14) . ?
C22 C23 1.528(11) . ?
C23 C24 1.515(12) . ?
C24 C25 1.522(10) . ?
C25 C26 1.531(12) . ?
C26 C27 1.534(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 O2 111.62(14) . . ?
C3 O2 O1 108.14(16) . . ?
C2 O3 C3 113.40(17) . . ?
C10 N11 C2 127.65(19) . . ?
O1 C1 C2 110.85(17) . . ?
O1 C1 C11 106.27(18) . . ?
O1 C1 C12 104.59(16) . . ?
C2 C1 C11 111.63(18) . . ?
C2 C1 C12 110.97(18) . . ?
C12 C1 C11 112.20(17) . . ?
O3 C2 N11 108.90(18) . . ?
O3 C2 C1 113.95(18) . . ?
N11 C2 C1 111.98(18) . . ?
O2 C3 O3 108.05(18) . . ?
O2 C3 C4 112.0(2) . . ?
O2 C3 C13 104.9(2) . . ?
O3 C3 C4 110.5(2) . . ?
O3 C3 C13 106.4(2) . . ?
C13 C3 C4 114.6(2) . . ?
C5 C4 C3 114.5(2) . . ?
C4 C5 C11 116.4(2) . . ?
C7 C6 C11 111.71(19) . . ?
C14 C6 C7 109.7(2) . . ?
C14 C6 C11 111.9(2) . . ?
C8 C7 C6 112.87(19) . . ?
C7 C8 C12 110.51(19) . . ?
C10 C9 C12 113.47(18) . . ?
C10 C9 C15 110.63(18) . . ?
C15 C9 C12 113.82(17) . . ?
O10 C10 N11 121.2(2) . . ?
O10 C10 C9 120.0(2) . . ?
N11 C10 C9 118.7(2) . . ?
C1 C11 C6 112.0(2) . . ?
C5 C11 C1 112.42(19) . . ?
C5 C11 C6 111.0(2) . . ?
C1 C12 C8 110.79(17) . . ?
C1 C12 C9 110.62(17) . . ?
C8 C12 C9 114.42(18) . . ?
O20 C21 O21 122.1(13) . . ?
O20 C21 C22 127.3(13) . . ?
O21 C21 C22 108.4(14) . . ?
C21 C22 C23 112.8(9) . . ?
C24 C23 C22 111.5(9) . . ?
C23 C24 C25 115.8(5) . . ?
C24 C25 C26 110.7(8) . . ?
C25 C26 C27 111.3(9) . . ?
O22 C27 C26 113.8(12) . . ?
O23 C27 O22 125.9(13) . . ?
O23 C27 C26 118.6(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H11 O20 0.86(3) 2.55(4) 3.320(14) 150(3) 1_545
N11 H11 O23 0.86(3) 2.38(4) 3.141(15) 149(3) 2_655
O21 H21 O10 0.84 1.81 2.586(17) 153.0 1_565
O22 H22 O10 0.84 1.74 2.575(17) 174.6 2_655

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 O2 C3 O3 -74.8(2) . . . . ?
O1 O2 C3 C4 47.2(2) . . . . ?
O1 O2 C3 C13 172.06(18) . . . . ?
O1 C1 C2 O3 -51.9(2) . . . . ?
O1 C1 C2 N11 72.3(2) . . . . ?
O1 C1 C11 C5 68.6(2) . . . . ?
O1 C1 C11 C6 -165.57(18) . . . . ?
O1 C1 C12 C8 170.60(17) . . . . ?
O1 C1 C12 C9 -61.4(2) . . . . ?
O2 O1 C1 C2 13.4(2) . . . . ?
O2 O1 C1 C11 -108.07(17) . . . . ?
O2 O1 C1 C12 133.07(16) . . . . ?
O2 C3 C4 C5 -95.0(3) . . . . ?
O3 C3 C4 C5 25.6(3) . . . . ?
C1 O1 O2 C3 46.8(2) . . . . ?
C2 O3 C3 O2 35.2(3) . . . . ?
C2 O3 C3 C4 -87.7(2) . . . . ?
C2 O3 C3 C13 147.3(2) . . . . ?
C2 N11 C10 O10 174.6(2) . . . . ?
C2 N11 C10 C9 -7.9(3) . . . . ?
C2 C1 C11 C5 -52.3(3) . . . . ?
C2 C1 C11 C6 73.5(2) . . . . ?
C2 C1 C12 C8 -69.8(2) . . . . ?
C2 C1 C12 C9 58.2(2) . . . . ?
C3 O3 C2 N11 -99.7(2) . . . . ?
C3 O3 C2 C1 26.1(3) . . . . ?
C3 C4 C5 C11 56.4(3) . . . . ?
C4 C5 C11 C1 -35.8(3) . . . . ?
C4 C5 C11 C6 -162.2(2) . . . . ?
C6 C7 C8 C12 56.6(3) . . . . ?
C7 C6 C11 C1 49.5(3) . . . . ?
C7 C6 C11 C5 176.0(2) . . . . ?
C7 C8 C12 C1 -57.6(2) . . . . ?
C7 C8 C12 C9 176.52(18) . . . . ?
C10 N11 C2 O3 146.1(2) . . . . ?
C10 N11 C2 C1 19.2(3) . . . . ?
C10 C9 C12 C1 -46.4(2) . . . . ?
C10 C9 C12 C8 79.5(2) . . . . ?
C11 C1 C2 O3 66.4(2) . . . . ?
C11 C1 C2 N11 -169.44(18) . . . . ?
C11 C1 C12 C8 55.8(2) . . . . ?
C11 C1 C12 C9 -176.20(18) . . . . ?
C11 C6 C7 C8 -52.6(3) . . . . ?
C12 C1 C2 O3 -167.64(18) . . . . ?
C12 C1 C2 N11 -43.5(2) . . . . ?
C12 C1 C11 C5 -177.6(2) . . . . ?
C12 C1 C11 C6 -51.8(2) . . . . ?
C12 C9 C10 O10 -161.1(2) . . . . ?
C12 C9 C10 N11 21.3(3) . . . . ?
C13 C3 C4 C5 145.7(2) . . . . ?
C14 C6 C7 C8 -177.3(2) . . . . ?
C14 C6 C11 C1 173.0(2) . . . . ?
C14 C6 C11 C5 -60.4(3) . . . . ?
C15 C9 C10 O10 -31.7(3) . . . . ?
C15 C9 C10 N11 150.7(2) . . . . ?
C15 C9 C12 C1 -174.14(17) . . . . ?
C15 C9 C12 C8 -48.2(2) . . . . ?
O20 C21 C22 C23 -25(3) . . . . ?
O21 C21 C22 C23 172.0(14) . . . . ?
C21 C22 C23 C24 168.4(12) . . . . ?
C22 C23 C24 C25 175.5(9) . . . . ?
C23 C24 C25 C26 -176.7(9) . . . . ?
C24 C25 C26 C27 -179.5(10) . . . . ?
C25 C26 C27 O22 -137.4(15) . . . . ?
C25 C26 C27 O23 56(2) . . . . ?

_olex2_date_sample_data_collection 2017-07-11
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.449
_oxdiff_exptl_absorpt_empirical_full_min 0.679

####################################################################### 
# 
# 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_cpd7_madiha30cult
_database_code_depnum_ccdc_archive 'CCDC 1569114'
_audit_update_record             
;
2017-08-15 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;
_audit_creation_date             2017-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            11-Aza:D-Mal
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C15 H23 N O4), C4 H6 O5'
_chemical_formula_sum            'C34 H52 N2 O13'
_chemical_formula_weight         696.77
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   10.43733(12)
_cell_length_b                   18.04445(19)
_cell_length_c                   18.6345(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3509.55(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12158
_cell_measurement_temperature    99.97(10)
_cell_measurement_theta_max      75.4300
_cell_measurement_theta_min      3.3990
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.842
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19371
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.500
_diffrn_reflns_theta_min         3.409
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     39.00 141.00   1.00    8.00    --  110.57 -30.00  60.00  102
  2  ω    -71.00  36.00   1.00    4.00    --  -40.57  77.00 120.00  107
  3  ω    -70.00  33.00   1.00    4.00    --  -40.57  57.00  30.00  103
  4  ω    -70.00  32.00   1.00    4.00    --  -40.57  57.00 -90.00  102
  5  ω    130.00 178.00   1.00    8.00    --  110.57  30.00 120.00   48
  6  ω    122.00 178.00   1.00    8.00    --  110.57 111.00  90.00   56
  7  ω     80.00 118.00   1.00    8.00    --  110.57  30.00 120.00   38
  8  ω     53.00 141.00   1.00    8.00    --  110.57 -30.00 150.00   88
  9  ω     45.00 115.00   1.00    8.00    --  110.57-111.00  60.00   70
 10  ω     33.00 139.00   1.00    8.00    --  110.57 -30.00 -60.00  106
 11  ω     33.00 115.00   1.00    8.00    --  110.57-111.00 -90.00   82
 12  ω     32.00 130.00   1.00    8.00    --  110.57 -77.00  90.00   98
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0679821000
_diffrn_orient_matrix_UB_12      0.0525212000
_diffrn_orient_matrix_UB_13      -0.0529089000
_diffrn_orient_matrix_UB_21      -0.1049696000
_diffrn_orient_matrix_UB_22      0.0150924000
_diffrn_orient_matrix_UB_23      0.0563410000
_diffrn_orient_matrix_UB_31      0.0782247000
_diffrn_orient_matrix_UB_32      0.0657088000
_diffrn_orient_matrix_UB_33      0.0292547000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                6062
_reflns_number_total             6284
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 2581 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         6284
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0284
_refine_ls_restrained_S_all      1.006
_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)+(0.0420P)²+0.4980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0725
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O22A-C23
 1.38 with sigma of 0.02
 O22A-C23A
 1.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C23) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.003
4. Rigid body (RIGU) restrains
 O22A, C22, C23A, C24
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: O22(0.9) H22(0.9) O22A(0.1) H22A(0.1) H22C(0.1) C23(0.9) H23A(0.9)
 H23B(0.9) C23A(0.1) H23C(0.1)
6.a Riding coordinates:
 C22(H22C,H22B), C23(H23A,H23B)
6.b Ternary CH refined with riding coordinates:
 C2(H2), C6(H6), C9(H9), C11(H11A), C12(H12), C2A(H2A), C6A(H6A), C9A(H9A),
 C11A(H11C), C12A(H12A), C23A(H23C)
6.c Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C4A(H4AA,H4AB), C5A(H5AA,
 H5AB), C7A(H7AA,H7AB), C8A(H8AA,H8AB)
6.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C13A(H13D,H13E,
 H13F), C14A(H14D,H14E,H14F), C15A(H15D,H15E,H15F)
6.e Idealised tetrahedral OH refined as rotating group:
 O22A(H22A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.72468(13) 0.73264(8) 0.33850(8) 0.0251(3) Uani 1 1 d . . . . .
O2 O 0.85440(14) 0.70303(8) 0.32931(8) 0.0284(3) Uani 1 1 d . . . . .
O3 O 0.79630(13) 0.57940(8) 0.32644(8) 0.0257(3) Uani 1 1 d . . . . .
O10 O 0.81739(14) 0.66060(8) 0.55060(7) 0.0257(3) Uani 1 1 d . . . . .
N11 N 0.76365(16) 0.60756(9) 0.44633(9) 0.0215(3) Uani 1 1 d . . . . .
H11 H 0.819(3) 0.5757(17) 0.4539(16) 0.043(8) Uiso 1 1 d . . . . .
C1 C 0.63343(18) 0.67387(10) 0.35576(10) 0.0201(4) Uani 1 1 d . . . . .
C2 C 0.70191(18) 0.60248(11) 0.37646(10) 0.0198(4) Uani 1 1 d . . . . .
H2 H 0.6359 0.5624 0.3794 0.024 Uiso 1 1 calc R . . . .
C3 C 0.8471(2) 0.63972(13) 0.28466(11) 0.0303(5) Uani 1 1 d . . . . .
C4 C 0.7638(2) 0.65250(14) 0.21824(11) 0.0357(5) Uani 1 1 d . . . . .
H4A H 0.7644 0.7061 0.2067 0.043 Uiso 1 1 calc R . . . .
H4B H 0.8028 0.6260 0.1772 0.043 Uiso 1 1 calc R . . . .
C5 C 0.6249(2) 0.62705(13) 0.22622(11) 0.0312(5) Uani 1 1 d . . . . .
H5A H 0.6244 0.5726 0.2324 0.037 Uiso 1 1 calc R . . . .
H5B H 0.5791 0.6382 0.1810 0.037 Uiso 1 1 calc R . . . .
C6 C 0.4291(2) 0.61566(11) 0.30651(11) 0.0248(4) Uani 1 1 d . . . . .
H6 H 0.4582 0.5653 0.3219 0.030 Uiso 1 1 calc R . . . .
C7 C 0.3566(2) 0.65034(11) 0.36867(11) 0.0263(4) Uani 1 1 d . . . . .
H7A H 0.2807 0.6195 0.3800 0.032 Uiso 1 1 calc R . . . .
H7B H 0.3259 0.7001 0.3543 0.032 Uiso 1 1 calc R . . . .
C8 C 0.44013(19) 0.65739(11) 0.43563(11) 0.0239(4) Uani 1 1 d . . . . .
H8A H 0.4675 0.6075 0.4517 0.029 Uiso 1 1 calc R . . . .
H8B H 0.3900 0.6804 0.4748 0.029 Uiso 1 1 calc R . . . .
C9 C 0.64798(18) 0.71911(11) 0.48418(10) 0.0216(4) Uani 1 1 d . . . . .
H9 H 0.6960 0.7656 0.4729 0.026 Uiso 1 1 calc R . . . .
C10 C 0.74837(19) 0.65957(10) 0.49587(10) 0.0202(4) Uani 1 1 d . . . . .
C11 C 0.5493(2) 0.66178(11) 0.28863(10) 0.0234(4) Uani 1 1 d . . . . .
H11A H 0.5193 0.7117 0.2723 0.028 Uiso 1 1 calc R . . . .
C12 C 0.55837(18) 0.70491(10) 0.41954(10) 0.0201(4) Uani 1 1 d . . . . .
H12 H 0.5256 0.7545 0.4042 0.024 Uiso 1 1 calc R . . . .
C13 C 0.9852(2) 0.62070(16) 0.26839(14) 0.0414(6) Uani 1 1 d . . . . .
H13A H 1.0342 0.6191 0.3132 0.062 Uiso 1 1 calc GR . . . .
H13B H 1.0216 0.6585 0.2366 0.062 Uiso 1 1 calc GR . . . .
H13C H 0.9892 0.5722 0.2448 0.062 Uiso 1 1 calc GR . . . .
C14 C 0.3416(2) 0.60599(13) 0.24123(12) 0.0322(5) Uani 1 1 d . . . . .
H14A H 0.2663 0.5768 0.2549 0.048 Uiso 1 1 calc GR . . . .
H14B H 0.3883 0.5803 0.2030 0.048 Uiso 1 1 calc GR . . . .
H14C H 0.3140 0.6548 0.2240 0.048 Uiso 1 1 calc GR . . . .
C15 C 0.5760(2) 0.73403(14) 0.55454(12) 0.0325(5) Uani 1 1 d . . . . .
H15A H 0.5317 0.6888 0.5698 0.049 Uiso 1 1 calc GR . . . .
H15B H 0.5132 0.7737 0.5470 0.049 Uiso 1 1 calc GR . . . .
H15C H 0.6372 0.7491 0.5917 0.049 Uiso 1 1 calc GR . . . .
O1A O 0.66199(13) 0.27912(7) 0.33211(7) 0.0225(3) Uani 1 1 d . . . . .
O2A O 0.53246(13) 0.31089(7) 0.33217(8) 0.0233(3) Uani 1 1 d . . . . .
O3A O 0.59564(13) 0.43330(7) 0.34033(7) 0.0205(3) Uani 1 1 d . . . . .
O10A O 0.61828(14) 0.33220(8) 0.55814(7) 0.0250(3) Uani 1 1 d . . . . .
N11A N 0.65038(16) 0.39369(9) 0.45496(9) 0.0206(3) Uani 1 1 d . . . . .
H11B H 0.602(3) 0.4301(14) 0.4716(14) 0.027(6) Uiso 1 1 d . . . . .
C1A C 0.75887(19) 0.33391(10) 0.35109(10) 0.0200(4) Uani 1 1 d . . . . .
C2A C 0.69793(18) 0.40431(10) 0.38223(10) 0.0190(4) Uani 1 1 d . . . . .
H2A H 0.7662 0.4431 0.3843 0.023 Uiso 1 1 calc R . . . .
C3A C 0.5363(2) 0.37893(10) 0.29451(10) 0.0222(4) Uani 1 1 d . . . . .
C4A C 0.6101(2) 0.37403(11) 0.22341(11) 0.0247(4) Uani 1 1 d . . . . .
H4AA H 0.6039 0.3226 0.2052 0.030 Uiso 1 1 calc R . . . .
H4AB H 0.5678 0.4068 0.1880 0.030 Uiso 1 1 calc R . . . .
C5A C 0.7516(2) 0.39532(11) 0.22792(10) 0.0249(4) Uani 1 1 d . . . . .
H5AA H 0.7572 0.4485 0.2406 0.030 Uiso 1 1 calc R . . . .
H5AB H 0.7899 0.3894 0.1797 0.030 Uiso 1 1 calc R . . . .
C6A C 0.96148(19) 0.39063(12) 0.29657(11) 0.0256(4) Uani 1 1 d . . . . .
H6A H 0.9422 0.4413 0.3154 0.031 Uiso 1 1 calc R . . . .
C7A C 1.0383(2) 0.34894(12) 0.35387(12) 0.0283(4) Uani 1 1 d . . . . .
H7AA H 1.0634 0.2999 0.3348 0.034 Uiso 1 1 calc R . . . .
H7AB H 1.1176 0.3769 0.3645 0.034 Uiso 1 1 calc R . . . .
C8A C 0.9628(2) 0.33813(12) 0.42315(11) 0.0264(4) Uani 1 1 d . . . . .
H8AA H 0.9405 0.3870 0.4438 0.032 Uiso 1 1 calc R . . . .
H8AB H 1.0159 0.3110 0.4585 0.032 Uiso 1 1 calc R . . . .
C9A C 0.7583(2) 0.27416(11) 0.47363(10) 0.0226(4) Uani 1 1 d . . . . .
H9A H 0.7005 0.2331 0.4578 0.027 Uiso 1 1 calc R . . . .
C10A C 0.67134(18) 0.33613(11) 0.49866(10) 0.0209(4) Uani 1 1 d . . . . .
C11A C 0.83321(19) 0.35123(11) 0.28175(10) 0.0227(4) Uani 1 1 d . . . . .
H11C H 0.8540 0.3027 0.2587 0.027 Uiso 1 1 calc R . . . .
C12A C 0.84056(19) 0.29433(10) 0.40773(10) 0.0219(4) Uani 1 1 d . . . . .
H12A H 0.8683 0.2464 0.3858 0.026 Uiso 1 1 calc R . . . .
C13A C 0.3970(2) 0.39975(12) 0.28614(12) 0.0288(4) Uani 1 1 d . . . . .
H13D H 0.3549 0.3984 0.3331 0.043 Uiso 1 1 calc GR . . . .
H13E H 0.3549 0.3645 0.2538 0.043 Uiso 1 1 calc GR . . . .
H13F H 0.3907 0.4498 0.2661 0.043 Uiso 1 1 calc GR . . . .
C14A C 1.0414(2) 0.39926(13) 0.22797(12) 0.0332(5) Uani 1 1 d . . . . .
H14D H 1.0630 0.3502 0.2090 0.050 Uiso 1 1 calc GR . . . .
H14E H 1.1204 0.4264 0.2390 0.050 Uiso 1 1 calc GR . . . .
H14F H 0.9919 0.4268 0.1921 0.050 Uiso 1 1 calc GR . . . .
C15A C 0.8356(2) 0.24353(13) 0.53686(11) 0.0308(5) Uani 1 1 d . . . . .
H15D H 0.8891 0.2830 0.5570 0.046 Uiso 1 1 calc GR . . . .
H15E H 0.8903 0.2029 0.5202 0.046 Uiso 1 1 calc GR . . . .
H15F H 0.7769 0.2251 0.5738 0.046 Uiso 1 1 calc GR . . . .
O20 O -0.01151(18) 0.52303(10) 0.46911(12) 0.0518(5) Uani 1 1 d . . . . .
O21 O 0.04066(15) 0.60088(8) 0.55720(8) 0.0291(3) Uani 1 1 d . . . . .
H21 H -0.044(3) 0.6146(16) 0.5575(16) 0.042(8) Uiso 1 1 d . . . . .
O22 O 0.2236(2) 0.48082(13) 0.44562(11) 0.0468(5) Uani 0.9 1 d . . P A 1
H22 H 0.152(4) 0.473(2) 0.4265(19) 0.049(10) Uiso 0.9 1 d . . P B 1
O22A O 0.1660(14) 0.4190(8) 0.5673(9) 0.035(3) Uani 0.1 1 d D U P A 2
H22A H 0.1317 0.4175 0.5265 0.053 Uiso 0.1 1 calc GR . P A 2
O23 O 0.40716(16) 0.39698(9) 0.59374(8) 0.0320(3) Uani 1 1 d . . . . .
H23 H 0.485(3) 0.3802(17) 0.5819(16) 0.048(8) Uiso 1 1 d . . . . .
O24 O 0.46838(16) 0.49548(9) 0.52997(10) 0.0382(4) Uani 1 1 d . . . . .
C21 C 0.0662(2) 0.55035(11) 0.50984(11) 0.0263(4) Uani 1 1 d . . . . .
C22 C 0.2060(2) 0.52740(13) 0.50533(11) 0.0272(4) Uani 1 1 d . U . . .
H22C H 0.2179 0.4939 0.4638 0.033 Uiso 0.1 1 d R . P A 2
H22B H 0.2593 0.5720 0.4973 0.033 Uiso 1 1 d R . . A .
C23 C 0.2499(5) 0.4901(2) 0.5731(4) 0.0345(11) Uani 0.9 1 d D U P A 1
H23A H 0.2509 0.5274 0.6121 0.041 Uiso 0.9 1 d R . P A 1
H23B H 0.1919 0.4489 0.5865 0.041 Uiso 0.9 1 d R . P A 1
C23A C 0.259(5) 0.477(2) 0.569(4) 0.024(5) Uani 0.1 1 d D U P A 2
H23C H 0.2468 0.5047 0.6147 0.029 Uiso 0.1 1 calc R . P A 2
C24 C 0.3875(2) 0.46181(12) 0.56281(11) 0.0288(4) Uani 1 1 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
O1 O2 1.466(2) . ?
O1 C1 1.461(2) . ?
O2 C3 1.415(3) . ?
O3 C2 1.419(2) . ?
O3 C3 1.440(3) . ?
O10 C10 1.249(2) . ?
N11 C2 1.456(2) . ?
N11 C10 1.326(3) . ?
C1 C2 1.523(3) . ?
C1 C11 1.544(3) . ?
C1 C12 1.530(3) . ?
C3 C4 1.530(3) . ?
C3 C13 1.512(3) . ?
C4 C5 1.529(3) . ?
C5 C11 1.539(3) . ?
C6 C7 1.519(3) . ?
C6 C11 1.542(3) . ?
C6 C14 1.531(3) . ?
C7 C8 1.528(3) . ?
C8 C12 1.532(3) . ?
C9 C10 1.516(3) . ?
C9 C12 1.546(3) . ?
C9 C15 1.535(3) . ?
O1A O2A 1.4685(19) . ?
O1A C1A 1.458(2) . ?
O2A C3A 1.415(2) . ?
O3A C2A 1.422(2) . ?
O3A C3A 1.440(2) . ?
O10A C10A 1.241(2) . ?
N11A C2A 1.456(2) . ?
N11A C10A 1.338(3) . ?
C1A C2A 1.535(3) . ?
C1A C11A 1.539(3) . ?
C1A C12A 1.533(3) . ?
C3A C4A 1.535(3) . ?
C3A C13A 1.511(3) . ?
C4A C5A 1.529(3) . ?
C5A C11A 1.538(3) . ?
C6A C7A 1.532(3) . ?
C6A C11A 1.541(3) . ?
C6A C14A 1.534(3) . ?
C7A C8A 1.525(3) . ?
C8A C12A 1.528(3) . ?
C9A C10A 1.513(3) . ?
C9A C12A 1.542(3) . ?
C9A C15A 1.531(3) . ?
O20 C21 1.215(3) . ?
O21 C21 1.297(3) . ?
O22 C22 1.406(3) . ?
O22A C23A 1.43(3) . ?
O23 C24 1.320(3) . ?
O24 C24 1.207(3) . ?
C21 C22 1.519(3) . ?
C22 C23 1.503(8) . ?
C22 C23A 1.60(6) . ?
C23 C24 1.536(5) . ?
C23A C24 1.37(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
C1 O1 O2 111.30(13) . . ?
C3 O2 O1 108.26(14) . . ?
C2 O3 C3 112.90(15) . . ?
C10 N11 C2 127.88(17) . . ?
O1 C1 C2 111.33(15) . . ?
O1 C1 C11 107.15(14) . . ?
O1 C1 C12 103.83(14) . . ?
C2 C1 C11 110.65(16) . . ?
C2 C1 C12 110.70(15) . . ?
C12 C1 C11 112.95(16) . . ?
O3 C2 N11 107.38(15) . . ?
O3 C2 C1 114.08(16) . . ?
N11 C2 C1 112.40(15) . . ?
O2 C3 O3 108.19(16) . . ?
O2 C3 C4 112.62(19) . . ?
O2 C3 C13 104.47(18) . . ?
O3 C3 C4 110.01(17) . . ?
O3 C3 C13 106.7(2) . . ?
C13 C3 C4 114.43(19) . . ?
C5 C4 C3 114.53(18) . . ?
C4 C5 C11 115.95(18) . . ?
C7 C6 C11 110.37(16) . . ?
C7 C6 C14 110.80(17) . . ?
C14 C6 C11 112.05(17) . . ?
C6 C7 C8 111.88(16) . . ?
C7 C8 C12 110.28(16) . . ?
C10 C9 C12 114.36(15) . . ?
C10 C9 C15 109.85(16) . . ?
C15 C9 C12 113.49(16) . . ?
O10 C10 N11 120.65(18) . . ?
O10 C10 C9 120.36(17) . . ?
N11 C10 C9 118.98(17) . . ?
C5 C11 C1 112.23(17) . . ?
C5 C11 C6 111.13(16) . . ?
C6 C11 C1 111.34(15) . . ?
C1 C12 C8 111.07(15) . . ?
C1 C12 C9 110.86(15) . . ?
C8 C12 C9 115.30(16) . . ?
C1A O1A O2A 111.93(12) . . ?
C3A O2A O1A 108.19(13) . . ?
C2A O3A C3A 113.41(14) . . ?
C10A N11A C2A 127.81(17) . . ?
O1A C1A C2A 111.45(15) . . ?
O1A C1A C11A 106.48(14) . . ?
O1A C1A C12A 103.69(14) . . ?
C2A C1A C11A 111.00(15) . . ?
C12A C1A C2A 110.84(15) . . ?
C12A C1A C11A 113.09(16) . . ?
O3A C2A N11A 107.67(15) . . ?
O3A C2A C1A 114.08(15) . . ?
N11A C2A C1A 112.61(15) . . ?
O2A C3A O3A 108.02(14) . . ?
O2A C3A C4A 113.11(16) . . ?
O2A C3A C13A 103.86(16) . . ?
O3A C3A C4A 109.60(15) . . ?
O3A C3A C13A 107.80(16) . . ?
C13A C3A C4A 114.09(17) . . ?
C5A C4A C3A 115.00(16) . . ?
C4A C5A C11A 116.16(16) . . ?
C7A C6A C11A 110.66(17) . . ?
C7A C6A C14A 110.24(17) . . ?
C14A C6A C11A 111.71(17) . . ?
C8A C7A C6A 112.49(17) . . ?
C7A C8A C12A 109.77(17) . . ?
C10A C9A C12A 113.88(16) . . ?
C10A C9A C15A 110.21(16) . . ?
C15A C9A C12A 113.84(17) . . ?
O10A C10A N11A 120.99(18) . . ?
O10A C10A C9A 120.03(17) . . ?
N11A C10A C9A 118.95(17) . . ?
C1A C11A C6A 112.41(16) . . ?
C5A C11A C1A 111.93(16) . . ?
C5A C11A C6A 111.06(16) . . ?
C1A C12A C9A 110.39(16) . . ?
C8A C12A C1A 110.66(16) . . ?
C8A C12A C9A 115.93(16) . . ?
O20 C21 O21 125.0(2) . . ?
O20 C21 C22 119.72(19) . . ?
O21 C21 C22 115.27(18) . . ?
O22 C22 C21 109.40(19) . . ?
O22 C22 C23 111.0(3) . . ?
C21 C22 C23A 116.7(19) . . ?
C23 C22 C21 111.6(2) . . ?
C22 C23 C24 109.2(4) . . ?
O22A C23A C22 99(3) . . ?
C24 C23A O22A 122(4) . . ?
C24 C23A C22 113(4) . . ?
O23 C24 C23 112.7(3) . . ?
O23 C24 C23A 107(2) . . ?
O24 C24 O23 124.0(2) . . ?
O24 C24 C23 123.4(3) . . ?
O24 C24 C23A 129(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
N11 H11 O20 0.83(3) 2.03(3) 2.831(2) 164(3) 1_655
N11A H11B O24 0.89(3) 2.12(3) 2.989(2) 165(2) .
O21 H21 O10 0.92(3) 1.67(3) 2.570(2) 165(3) 1_455
O23 H23 O10A 0.89(3) 1.70(3) 2.581(2) 169(3) .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 O2 C3 O3 -75.51(19) . . . . ?
O1 O2 C3 C4 46.3(2) . . . . ?
O1 O2 C3 C13 171.05(17) . . . . ?
O1 C1 C2 O3 -51.2(2) . . . . ?
O1 C1 C2 N11 71.32(19) . . . . ?
O1 C1 C11 C5 69.0(2) . . . . ?
O1 C1 C11 C6 -165.67(15) . . . . ?
O1 C1 C12 C8 168.59(15) . . . . ?
O1 C1 C12 C9 -61.85(18) . . . . ?
O2 O1 C1 C2 13.3(2) . . . . ?
O2 O1 C1 C11 -107.80(16) . . . . ?
O2 O1 C1 C12 132.45(14) . . . . ?
O2 C3 C4 C5 -95.2(2) . . . . ?
O3 C3 C4 C5 25.5(3) . . . . ?
C1 O1 O2 C3 46.85(19) . . . . ?
C2 O3 C3 O2 36.1(2) . . . . ?
C2 O3 C3 C4 -87.3(2) . . . . ?
C2 O3 C3 C13 148.00(17) . . . . ?
C2 N11 C10 O10 -172.89(18) . . . . ?
C2 N11 C10 C9 5.5(3) . . . . ?
C2 C1 C11 C5 -52.5(2) . . . . ?
C2 C1 C11 C6 72.8(2) . . . . ?
C2 C1 C12 C8 -71.8(2) . . . . ?
C2 C1 C12 C9 57.7(2) . . . . ?
C3 O3 C2 N11 -100.28(18) . . . . ?
C3 O3 C2 C1 25.0(2) . . . . ?
C3 C4 C5 C11 57.4(3) . . . . ?
C4 C5 C11 C1 -36.5(3) . . . . ?
C4 C5 C11 C6 -161.93(19) . . . . ?
C6 C7 C8 C12 58.9(2) . . . . ?
C7 C6 C11 C1 53.5(2) . . . . ?
C7 C6 C11 C5 179.42(16) . . . . ?
C7 C8 C12 C1 -55.4(2) . . . . ?
C7 C8 C12 C9 177.45(16) . . . . ?
C10 N11 C2 O3 138.63(19) . . . . ?
C10 N11 C2 C1 12.4(3) . . . . ?
C10 C9 C12 C1 -40.4(2) . . . . ?
C10 C9 C12 C8 86.9(2) . . . . ?
C11 C1 C2 O3 67.8(2) . . . . ?
C11 C1 C2 N11 -169.64(15) . . . . ?
C11 C1 C12 C8 52.9(2) . . . . ?
C11 C1 C12 C9 -177.58(15) . . . . ?
C11 C6 C7 C8 -57.9(2) . . . . ?
C12 C1 C2 O3 -166.19(15) . . . . ?
C12 C1 C2 N11 -43.6(2) . . . . ?
C12 C1 C11 C5 -177.24(16) . . . . ?
C12 C1 C11 C6 -51.9(2) . . . . ?
C12 C9 C10 O10 -172.36(17) . . . . ?
C12 C9 C10 N11 9.2(3) . . . . ?
C13 C3 C4 C5 145.7(2) . . . . ?
C14 C6 C7 C8 177.41(17) . . . . ?
C14 C6 C11 C1 177.51(17) . . . . ?
C14 C6 C11 C5 -56.6(2) . . . . ?
C15 C9 C10 O10 -43.4(2) . . . . ?
C15 C9 C10 N11 138.19(19) . . . . ?
C15 C9 C12 C1 -167.48(17) . . . . ?
C15 C9 C12 C8 -40.2(2) . . . . ?
O1A O2A C3A O3A -75.53(16) . . . . ?
O1A O2A C3A C4A 45.96(19) . . . . ?
O1A O2A C3A C13A 170.18(14) . . . . ?
O1A C1A C2A O3A -49.4(2) . . . . ?
O1A C1A C2A N11A 73.75(19) . . . . ?
O1A C1A C11A C5A 70.47(19) . . . . ?
O1A C1A C11A C6A -163.73(15) . . . . ?
O1A C1A C12A C8A 168.88(15) . . . . ?
O1A C1A C12A C9A -61.42(19) . . . . ?
O2A O1A C1A C2A 12.86(19) . . . . ?
O2A O1A C1A C11A -108.32(15) . . . . ?
O2A O1A C1A C12A 132.15(14) . . . . ?
O2A C3A C4A C5A -93.6(2) . . . . ?
O3A C3A C4A C5A 27.0(2) . . . . ?
C1A O1A O2A C3A 46.68(17) . . . . ?
C2A O3A C3A O2A 37.4(2) . . . . ?
C2A O3A C3A C4A -86.21(18) . . . . ?
C2A O3A C3A C13A 149.08(16) . . . . ?
C2A N11A C10A O10A -175.62(17) . . . . ?
C2A N11A C10A C9A 2.6(3) . . . . ?
C2A C1A C11A C5A -51.0(2) . . . . ?
C2A C1A C11A C6A 74.8(2) . . . . ?
C2A C1A C12A C8A -71.4(2) . . . . ?
C2A C1A C12A C9A 58.3(2) . . . . ?
C3A O3A C2A N11A -102.89(17) . . . . ?
C3A O3A C2A C1A 22.9(2) . . . . ?
C3A C4A C5A C11A 57.1(2) . . . . ?
C4A C5A C11A C1A -37.9(2) . . . . ?
C4A C5A C11A C6A -164.47(17) . . . . ?
C6A C7A C8A C12A 59.4(2) . . . . ?
C7A C6A C11A C1A 50.1(2) . . . . ?
C7A C6A C11A C5A 176.33(17) . . . . ?
C7A C8A C12A C1A -57.4(2) . . . . ?
C7A C8A C12A C9A 175.92(16) . . . . ?
C10A N11A C2A O3A 137.66(18) . . . . ?
C10A N11A C2A C1A 11.0(3) . . . . ?
C10A C9A C12A C1A -45.0(2) . . . . ?
C10A C9A C12A C8A 81.8(2) . . . . ?
C11A C1A C2A O3A 69.2(2) . . . . ?
C11A C1A C2A N11A -167.74(15) . . . . ?
C11A C1A C12A C8A 54.0(2) . . . . ?
C11A C1A C12A C9A -176.33(15) . . . . ?
C11A C6A C7A C8A -55.4(2) . . . . ?
C12A C1A C2A O3A -164.30(15) . . . . ?
C12A C1A C2A N11A -41.2(2) . . . . ?
C12A C1A C11A C5A -176.30(16) . . . . ?
C12A C1A C11A C6A -50.5(2) . . . . ?
C12A C9A C10A O10A -166.76(17) . . . . ?
C12A C9A C10A N11A 15.0(3) . . . . ?
C13A C3A C4A C5A 147.95(18) . . . . ?
C14A C6A C7A C8A -179.47(18) . . . . ?
C14A C6A C11A C1A 173.29(17) . . . . ?
C14A C6A C11A C5A -60.4(2) . . . . ?
C15A C9A C10A O10A -37.4(3) . . . . ?
C15A C9A C10A N11A 144.37(18) . . . . ?
C15A C9A C12A C1A -172.47(17) . . . . ?
C15A C9A C12A C8A -45.7(2) . . . . ?
O20 C21 C22 O22 6.4(3) . . . . ?
O20 C21 C22 C23 -116.8(3) . . . . ?
O20 C21 C22 C23A -108.1(17) . . . . ?
O21 C21 C22 O22 -171.56(19) . . . . ?
O21 C21 C22 C23 65.3(3) . . . . ?
O21 C21 C22 C23A 74.0(17) . . . . ?
O22 C22 C23 C24 52.5(4) . . . . ?
O22A C23A C24 O23 -33(6) . . . . ?
O22A C23A C24 O24 140(3) . . . . ?
C21 C22 C23 C24 174.8(2) . . . . ?
C21 C22 C23A O22A 53(3) . . . . ?
C21 C22 C23A C24 -176.7(19) . . . . ?
C22 C23 C24 O23 -141.8(2) . . . . ?
C22 C23 C24 O24 38.3(5) . . . . ?
C22 C23A C24 O23 -151.3(19) . . . . ?
C22 C23A C24 O24 22(4) . . . . ?

_olex2_date_sample_data_collection 2017-06-19
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.356
_oxdiff_exptl_absorpt_empirical_full_min 0.866
