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

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

data_wdb1002
_database_code_depnum_ccdc_archive 'CCDC 1512412'
_audit_update_record             
;
2016-10-27 deposited with the CCDC.
2016-11-29 downloaded from the CCDC.
;
_audit_creation_date             2016-05-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H42 N6 O8'
_chemical_formula_sum            'C28 H42 N6 O8'
_chemical_formula_weight         590.67
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C28 H40 N6 O8'
_chemical_oxdiff_usercomment     'Philippe Gilles'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.6767(4)
_cell_length_b                   13.4665(5)
_cell_length_c                   25.2462(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.061(3)
_cell_angle_gamma                90
_cell_volume                     3239.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7254
_cell_measurement_temperature    110.02(13)
_cell_measurement_theta_max      28.2260
_cell_measurement_theta_min      2.8430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            17986
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.456
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.02(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_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    -61.00  56.00   1.00   60.00    --  -17.31  19.00 -60.00  117
  2  ω    -93.00 -35.00   1.00   60.00    --  -17.31-178.00  60.00   58
  3  ω    -20.00  25.00   1.00   60.00    --  -17.31 -99.00 120.00   45
  4  ω    -20.00  25.00   1.00   60.00    --  -17.31 -99.00   0.00   45
  5  ω     -2.00  88.00   1.00   60.00    --   19.34  57.00   0.00   90
  6  ω     -6.00  92.00   1.00   60.00    --   19.34  38.00-180.00   98
  7  ω     -6.00  26.00   1.00   60.00    --   19.34  38.00 -60.00   32
  8  ω    -53.00  45.00   1.00   60.00    --   19.34 -38.00   0.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0696443000
_diffrn_orient_matrix_UB_12      0.0025467000
_diffrn_orient_matrix_UB_13      -0.0145286000
_diffrn_orient_matrix_UB_21      -0.0137751000
_diffrn_orient_matrix_UB_22      -0.0480129000
_diffrn_orient_matrix_UB_23      0.0093641000
_diffrn_orient_matrix_UB_31      -0.0225534000
_diffrn_orient_matrix_UB_32      0.0214514000
_diffrn_orient_matrix_UB_33      0.0226958000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4826
_reflns_number_total             6598
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         0.449
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         6598
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0618
_refine_ls_restrained_S_all      1.095
_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)+(0.0376P)²+3.8515P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1448
_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:
 C9(H9), C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), N16(H16), C23(H23)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C15(H15A,H15B,H15C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C37(H37A,
 H37B,H37C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C)
;
_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
N1 N -0.0560(2) 0.66860(15) 0.02546(7) 0.0221(4) Uani 1 1 d . . . . .
C2 C 0.0553(2) 0.66989(17) 0.06414(9) 0.0209(5) Uani 1 1 d . . . . .
C3 C 0.0941(2) 0.58729(17) 0.10041(9) 0.0205(5) Uani 1 1 d . . . . .
N4 N 0.0193(2) 0.50476(15) 0.09350(8) 0.0229(4) Uani 1 1 d . . . . .
C5 C -0.0952(2) 0.50368(18) 0.05219(9) 0.0231(5) Uani 1 1 d . . . . .
H5 H -0.1496 0.4447 0.0463 0.028 Uiso 1 1 calc R . . . .
C6 C -0.1340(2) 0.58348(18) 0.01948(9) 0.0210(5) Uani 1 1 d . . . . .
O7 O 0.14322(18) 0.74743(13) 0.07359(6) 0.0276(4) Uani 1 1 d . . . . .
C8 C 0.1166(3) 0.8340(2) 0.03926(11) 0.0327(6) Uani 1 1 d . . . . .
H8A H 0.0978 0.8925 0.0607 0.039 Uiso 1 1 calc R . . . .
H8B H 0.0336 0.8225 0.0109 0.039 Uiso 1 1 calc R . . . .
C9 C 0.2427(3) 0.8523(2) 0.01439(11) 0.0382(7) Uani 1 1 d . . . . .
H9 H 0.3252 0.8630 0.0437 0.046 Uiso 1 1 calc R . . . .
C10 C 0.2728(4) 0.7651(3) -0.01890(13) 0.0591(10) Uani 1 1 d . . . . .
H10A H 0.2860 0.7055 0.0037 0.089 Uiso 1 1 calc GR . . . .
H10B H 0.3583 0.7780 -0.0336 0.089 Uiso 1 1 calc GR . . . .
H10C H 0.1939 0.7550 -0.0485 0.089 Uiso 1 1 calc GR . . . .
C11 C 0.2175(4) 0.9472(2) -0.01918(14) 0.0575(9) Uani 1 1 d . . . . .
H11A H 0.1393 0.9367 -0.0490 0.086 Uiso 1 1 calc GR . . . .
H11B H 0.3024 0.9639 -0.0335 0.086 Uiso 1 1 calc GR . . . .
H11C H 0.1945 1.0017 0.0035 0.086 Uiso 1 1 calc GR . . . .
C12 C -0.2642(3) 0.58503(19) -0.02340(9) 0.0245(5) Uani 1 1 d . . . . .
O13 O -0.3141(2) 0.65785(14) -0.04742(7) 0.0381(5) Uani 1 1 d . . . . .
O14 O -0.32283(18) 0.49474(13) -0.03131(7) 0.0315(4) Uani 1 1 d . . . . .
C15 C -0.4547(3) 0.4897(2) -0.07020(11) 0.0367(7) Uani 1 1 d . . . . .
H15A H -0.4423 0.5225 -0.1037 0.055 Uiso 1 1 calc GR . . . .
H15B H -0.5292 0.5232 -0.0553 0.055 Uiso 1 1 calc GR . . . .
H15C H -0.4804 0.4200 -0.0776 0.055 Uiso 1 1 calc GR . . . .
N16 N 0.2081(2) 0.59934(15) 0.14178(7) 0.0223(4) Uani 1 1 d . . . . .
H16 H 0.2454 0.6591 0.1447 0.027 Uiso 1 1 calc R . . . .
N19 N 0.3730(2) 0.56953(15) 0.21886(8) 0.0248(5) Uani 1 1 d . . . . .
C20 C 0.4470(3) 0.50706(18) 0.25352(9) 0.0236(5) Uani 1 1 d . . . . .
C21 C 0.4245(2) 0.40408(18) 0.24964(9) 0.0222(5) Uani 1 1 d . . . . .
N22 N 0.3236(2) 0.36590(15) 0.21294(8) 0.0247(5) Uani 1 1 d . . . . .
C23 C 0.2441(3) 0.42813(18) 0.17770(10) 0.0253(5) Uani 1 1 d . . . . .
H23 H 0.1696 0.4026 0.1518 0.030 Uiso 1 1 calc R . . . .
C24 C 0.2724(2) 0.52924(17) 0.17979(9) 0.0208(5) Uani 1 1 d . . . . .
O25 O 0.54803(19) 0.53766(13) 0.29447(7) 0.0313(4) Uani 1 1 d . . . . .
C26 C 0.5640(3) 0.64401(19) 0.30390(11) 0.0404(7) Uani 1 1 d . . . . .
H26A H 0.4709 0.6764 0.2996 0.049 Uiso 1 1 calc R . . . .
H26B H 0.6174 0.6741 0.2779 0.049 Uiso 1 1 calc R . . . .
C27 C 0.6434(3) 0.6578(2) 0.36149(11) 0.0412(7) Uani 1 1 d . . . . .
H27 H 0.6490 0.7309 0.3686 0.049 Uiso 1 1 calc R . . . .
C28 C 0.5633(4) 0.6132(3) 0.40108(12) 0.0571(9) Uani 1 1 d . . . . .
H28A H 0.4665 0.6378 0.3940 0.086 Uiso 1 1 calc GR . . . .
H28B H 0.6077 0.6319 0.4376 0.086 Uiso 1 1 calc GR . . . .
H28C H 0.5632 0.5407 0.3976 0.086 Uiso 1 1 calc GR . . . .
C29 C 0.7927(4) 0.6191(3) 0.37026(14) 0.0644(11) Uani 1 1 d . . . . .
H29A H 0.7915 0.5469 0.3654 0.097 Uiso 1 1 calc GR . . . .
H29B H 0.8396 0.6354 0.4068 0.097 Uiso 1 1 calc GR . . . .
H29C H 0.8435 0.6499 0.3442 0.097 Uiso 1 1 calc GR . . . .
N30 N 0.5182(2) 0.34013(14) 0.28570(7) 0.0212(4) Uani 1 1 d . . . . .
C31 C 0.4779(2) 0.29975(18) 0.33108(9) 0.0222(5) Uani 1 1 d . . . . .
O32 O 0.54387(18) 0.23722(13) 0.35953(6) 0.0269(4) Uani 1 1 d . . . . .
O33 O 0.35578(18) 0.34063(12) 0.33605(6) 0.0258(4) Uani 1 1 d . . . . .
C34 C 0.2720(3) 0.2949(2) 0.37234(10) 0.0272(6) Uani 1 1 d . . . . .
C35 C 0.1422(3) 0.3613(2) 0.36285(11) 0.0380(7) Uani 1 1 d . . . . .
H35A H 0.1688 0.4292 0.3743 0.057 Uiso 1 1 calc GR . . . .
H35B H 0.0731 0.3362 0.3837 0.057 Uiso 1 1 calc GR . . . .
H35C H 0.1012 0.3612 0.3245 0.057 Uiso 1 1 calc GR . . . .
C36 C 0.2336(3) 0.1900(2) 0.35360(11) 0.0340(6) Uani 1 1 d . . . . .
H36A H 0.1872 0.1912 0.3159 0.051 Uiso 1 1 calc GR . . . .
H36B H 0.1700 0.1613 0.3757 0.051 Uiso 1 1 calc GR . . . .
H36C H 0.3190 0.1496 0.3571 0.051 Uiso 1 1 calc GR . . . .
C37 C 0.3508(3) 0.3008(2) 0.43049(10) 0.0335(6) Uani 1 1 d . . . . .
H37A H 0.4302 0.2546 0.4353 0.050 Uiso 1 1 calc GR . . . .
H37B H 0.2871 0.2830 0.4552 0.050 Uiso 1 1 calc GR . . . .
H37C H 0.3854 0.3686 0.4382 0.050 Uiso 1 1 calc GR . . . .
C38 C 0.6600(3) 0.33347(18) 0.28029(9) 0.0238(5) Uani 1 1 d . . . . .
O39 O 0.75808(18) 0.31346(14) 0.31588(7) 0.0302(4) Uani 1 1 d . . . . .
O40 O 0.66387(17) 0.35398(13) 0.22914(6) 0.0265(4) Uani 1 1 d . . . . .
C41 C 0.8023(3) 0.3644(2) 0.21308(10) 0.0317(6) Uani 1 1 d . . . . .
C42 C 0.8785(3) 0.4538(2) 0.24161(12) 0.0397(7) Uani 1 1 d . . . . .
H42A H 0.8195 0.5131 0.2340 0.060 Uiso 1 1 calc GR . . . .
H42B H 0.9672 0.4641 0.2286 0.060 Uiso 1 1 calc GR . . . .
H42C H 0.8978 0.4417 0.2805 0.060 Uiso 1 1 calc GR . . . .
C43 C 0.8863(3) 0.2689(2) 0.22344(12) 0.0429(7) Uani 1 1 d . . . . .
H43A H 0.9122 0.2580 0.2623 0.064 Uiso 1 1 calc GR . . . .
H43B H 0.9716 0.2740 0.2076 0.064 Uiso 1 1 calc GR . . . .
H43C H 0.8294 0.2130 0.2071 0.064 Uiso 1 1 calc GR . . . .
C44 C 0.7574(3) 0.3838(3) 0.15318(11) 0.0474(8) Uani 1 1 d . . . . .
H44A H 0.6999 0.3283 0.1367 0.071 Uiso 1 1 calc GR . . . .
H44B H 0.8409 0.3903 0.1363 0.071 Uiso 1 1 calc GR . . . .
H44C H 0.7026 0.4453 0.1479 0.071 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
N1 C2 1.322(3) . ?
N1 C6 1.366(3) . ?
C2 C3 1.448(3) . ?
C2 O7 1.342(3) . ?
C3 N4 1.321(3) . ?
C3 N16 1.390(3) . ?
N4 C5 1.383(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.367(3) . ?
C6 C12 1.511(3) . ?
O7 C8 1.449(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.487(4) . ?
C9 H9 1.0000 . ?
C9 C10 1.502(4) . ?
C9 C11 1.529(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O13 1.209(3) . ?
C12 O14 1.342(3) . ?
O14 C15 1.469(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N16 H16 0.8800 . ?
N16 C24 1.411(3) . ?
N19 C20 1.329(3) . ?
N19 C24 1.371(3) . ?
C20 C21 1.405(3) . ?
C20 O25 1.357(3) . ?
C21 N22 1.327(3) . ?
C21 N30 1.451(3) . ?
N22 C23 1.359(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.388(3) . ?
O25 C26 1.456(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.533(4) . ?
C27 H27 1.0000 . ?
C27 C28 1.494(4) . ?
C27 C29 1.515(5) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
N30 C31 1.384(3) . ?
N30 C38 1.405(3) . ?
C31 O32 1.213(3) . ?
C31 O33 1.330(3) . ?
O33 C34 1.461(3) . ?
C34 C35 1.527(4) . ?
C34 C36 1.516(4) . ?
C34 C37 1.533(3) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 O39 1.218(3) . ?
C38 O40 1.327(3) . ?
O40 C41 1.472(3) . ?
C41 C42 1.526(4) . ?
C41 C43 1.520(4) . ?
C41 C44 1.521(4) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 117.1(2) . . ?
N1 C2 C3 123.0(2) . . ?
N1 C2 O7 123.5(2) . . ?
O7 C2 C3 113.5(2) . . ?
N4 C3 C2 119.2(2) . . ?
N4 C3 N16 122.8(2) . . ?
N16 C3 C2 118.0(2) . . ?
C3 N4 C5 117.2(2) . . ?
N4 C5 H5 118.4 . . ?
C6 C5 N4 123.1(2) . . ?
C6 C5 H5 118.4 . . ?
N1 C6 C5 120.3(2) . . ?
N1 C6 C12 116.3(2) . . ?
C5 C6 C12 123.4(2) . . ?
C2 O7 C8 118.63(18) . . ?
O7 C8 H8A 110.1 . . ?
O7 C8 H8B 110.1 . . ?
O7 C8 C9 108.2(2) . . ?
H8A C8 H8B 108.4 . . ?
C9 C8 H8A 110.1 . . ?
C9 C8 H8B 110.1 . . ?
C8 C9 H9 108.6 . . ?
C8 C9 C10 111.2(3) . . ?
C8 C9 C11 108.0(3) . . ?
C10 C9 H9 108.6 . . ?
C10 C9 C11 111.8(3) . . ?
C11 C9 H9 108.6 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O13 C12 C6 125.5(2) . . ?
O13 C12 O14 122.6(2) . . ?
O14 C12 C6 111.8(2) . . ?
C12 O14 C15 115.9(2) . . ?
O14 C15 H15A 109.5 . . ?
O14 C15 H15B 109.5 . . ?
O14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C3 N16 H16 115.4 . . ?
C3 N16 C24 129.1(2) . . ?
C24 N16 H16 115.4 . . ?
C20 N19 C24 117.2(2) . . ?
N19 C20 C21 121.3(2) . . ?
N19 C20 O25 122.9(2) . . ?
O25 C20 C21 115.8(2) . . ?
C20 C21 N30 118.0(2) . . ?
N22 C21 C20 121.2(2) . . ?
N22 C21 N30 120.8(2) . . ?
C21 N22 C23 118.8(2) . . ?
N22 C23 H23 120.2 . . ?
N22 C23 C24 119.7(2) . . ?
C24 C23 H23 120.2 . . ?
N19 C24 N16 113.4(2) . . ?
N19 C24 C23 121.7(2) . . ?
C23 C24 N16 124.7(2) . . ?
C20 O25 C26 117.73(19) . . ?
O25 C26 H26A 110.3 . . ?
O25 C26 H26B 110.3 . . ?
O25 C26 C27 107.2(2) . . ?
H26A C26 H26B 108.5 . . ?
C27 C26 H26A 110.3 . . ?
C27 C26 H26B 110.3 . . ?
C26 C27 H27 107.0 . . ?
C28 C27 C26 110.7(3) . . ?
C28 C27 H27 107.0 . . ?
C28 C27 C29 110.9(3) . . ?
C29 C27 C26 113.8(3) . . ?
C29 C27 H27 107.0 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 N30 C21 121.12(19) . . ?
C31 N30 C38 118.45(19) . . ?
C38 N30 C21 119.40(19) . . ?
O32 C31 N30 124.6(2) . . ?
O32 C31 O33 128.0(2) . . ?
O33 C31 N30 107.40(19) . . ?
C31 O33 C34 118.98(18) . . ?
O33 C34 C35 100.7(2) . . ?
O33 C34 C36 109.2(2) . . ?
O33 C34 C37 109.9(2) . . ?
C35 C34 C37 112.2(2) . . ?
C36 C34 C35 110.3(2) . . ?
C36 C34 C37 113.6(2) . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
O39 C38 N30 126.2(2) . . ?
O39 C38 O40 127.8(2) . . ?
O40 C38 N30 105.98(19) . . ?
C38 O40 C41 118.00(18) . . ?
O40 C41 C42 109.5(2) . . ?
O40 C41 C43 110.9(2) . . ?
O40 C41 C44 100.1(2) . . ?
C43 C41 C42 112.8(2) . . ?
C43 C41 C44 111.6(3) . . ?
C44 C41 C42 111.4(2) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C41 C43 H43A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C41 C44 H44A 109.5 . . ?
C41 C44 H44B 109.5 . . ?
C41 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N4 3.1(3) . . . . ?
N1 C2 C3 N16 -175.9(2) . . . . ?
N1 C2 O7 C8 -0.9(3) . . . . ?
N1 C6 C12 O13 -10.3(4) . . . . ?
N1 C6 C12 O14 171.5(2) . . . . ?
C2 N1 C6 C5 -0.8(3) . . . . ?
C2 N1 C6 C12 177.5(2) . . . . ?
C2 C3 N4 C5 -1.7(3) . . . . ?
C2 C3 N16 C24 -175.3(2) . . . . ?
C2 O7 C8 C9 -122.3(2) . . . . ?
C3 C2 O7 C8 179.0(2) . . . . ?
C3 N4 C5 C6 -0.8(3) . . . . ?
C3 N16 C24 N19 -173.0(2) . . . . ?
C3 N16 C24 C23 10.0(4) . . . . ?
N4 C3 N16 C24 5.7(4) . . . . ?
N4 C5 C6 N1 2.2(4) . . . . ?
N4 C5 C6 C12 -176.0(2) . . . . ?
C5 C6 C12 O13 168.0(2) . . . . ?
C5 C6 C12 O14 -10.2(3) . . . . ?
C6 N1 C2 C3 -1.8(3) . . . . ?
C6 N1 C2 O7 178.1(2) . . . . ?
C6 C12 O14 C15 176.7(2) . . . . ?
O7 C2 C3 N4 -176.8(2) . . . . ?
O7 C2 C3 N16 4.2(3) . . . . ?
O7 C8 C9 C10 60.3(3) . . . . ?
O7 C8 C9 C11 -176.7(2) . . . . ?
O13 C12 O14 C15 -1.6(4) . . . . ?
N16 C3 N4 C5 177.3(2) . . . . ?
N19 C20 C21 N22 -3.5(4) . . . . ?
N19 C20 C21 N30 174.2(2) . . . . ?
N19 C20 O25 C26 7.0(4) . . . . ?
C20 N19 C24 N16 -174.4(2) . . . . ?
C20 N19 C24 C23 2.8(3) . . . . ?
C20 C21 N22 C23 2.0(3) . . . . ?
C20 C21 N30 C31 101.5(3) . . . . ?
C20 C21 N30 C38 -66.8(3) . . . . ?
C20 O25 C26 C27 160.5(2) . . . . ?
C21 C20 O25 C26 -173.1(2) . . . . ?
C21 N22 C23 C24 1.8(3) . . . . ?
C21 N30 C31 O32 171.3(2) . . . . ?
C21 N30 C31 O33 -7.5(3) . . . . ?
C21 N30 C38 O39 152.9(2) . . . . ?
C21 N30 C38 O40 -26.7(3) . . . . ?
N22 C21 N30 C31 -80.8(3) . . . . ?
N22 C21 N30 C38 111.0(3) . . . . ?
N22 C23 C24 N16 172.5(2) . . . . ?
N22 C23 C24 N19 -4.3(4) . . . . ?
C24 N19 C20 C21 1.1(3) . . . . ?
C24 N19 C20 O25 -179.0(2) . . . . ?
O25 C20 C21 N22 176.5(2) . . . . ?
O25 C20 C21 N30 -5.7(3) . . . . ?
O25 C26 C27 C28 -60.3(3) . . . . ?
O25 C26 C27 C29 65.4(3) . . . . ?
N30 C21 N22 C23 -175.7(2) . . . . ?
N30 C31 O33 C34 165.14(19) . . . . ?
N30 C38 O40 C41 172.8(2) . . . . ?
C31 N30 C38 O39 -15.7(4) . . . . ?
C31 N30 C38 O40 164.8(2) . . . . ?
C31 O33 C34 C35 -177.0(2) . . . . ?
C31 O33 C34 C36 -60.9(3) . . . . ?
C31 O33 C34 C37 64.4(3) . . . . ?
O32 C31 O33 C34 -13.6(4) . . . . ?
C38 N30 C31 O32 -20.4(3) . . . . ?
C38 N30 C31 O33 160.8(2) . . . . ?
C38 O40 C41 C42 -64.5(3) . . . . ?
C38 O40 C41 C43 60.5(3) . . . . ?
C38 O40 C41 C44 178.4(2) . . . . ?
O39 C38 O40 C41 -6.8(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-04-29
_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 1.446
_oxdiff_exptl_absorpt_empirical_full_min 0.768
####################################################################### 
# 
# 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_wdb1003
_database_code_depnum_ccdc_archive 'CCDC 1512413'
_audit_update_record             
;
2016-10-27 deposited with the CCDC.
2016-11-29 downloaded from the CCDC.
;
_audit_creation_date             2016-06-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H26 N6 O5, H2 O'
_chemical_formula_sum            'C19 H28 N6 O6'
_chemical_formula_weight         436.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H24 N6 O5'
_chemical_oxdiff_usercomment     PG20
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   17.7469(6)
_cell_length_b                   8.5054(3)
_cell_length_c                   28.7562(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4340.6(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9644
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      28.2800
_cell_measurement_theta_min      2.9930
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.951
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (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    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            28743
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.748
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_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    -20.00  25.00   1.00   30.00    --  -16.84 -99.00-150.00   45
  2  ω    -50.00  40.00   1.00   30.00    --   18.87 -57.00-150.00   90
  3  ω    -11.00  89.00   1.00   30.00    --   18.87  77.00 -30.00  100
  4  ω    -42.00  56.00   1.00   30.00    --  -16.84  38.00  30.00   98
  5  ω     35.00  60.00   1.00   30.00    --   18.87 178.00-150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0367968000
_diffrn_orient_matrix_UB_12      0.0159067000
_diffrn_orient_matrix_UB_13      -0.0083520000
_diffrn_orient_matrix_UB_21      0.0121099000
_diffrn_orient_matrix_UB_22      -0.0159956000
_diffrn_orient_matrix_UB_23      -0.0230420000
_diffrn_orient_matrix_UB_31      -0.0097162000
_diffrn_orient_matrix_UB_32      -0.0802807000
_diffrn_orient_matrix_UB_33      0.0029364000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3619
_reflns_number_total             4434
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         0.352
_refine_diff_density_min         -0.741
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         4434
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.061
_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)+(0.0857P)²+3.1025P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.1607
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O31(H31A,H31B)
2.b Ternary CH refined with riding coordinates:
 C9(H9), C27(H27)
2.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C26(H26A,H26B)
2.d Aromatic/amide H refined with riding coordinates:
 C5(H5), N16(H16), C23(H23)
2.e X=CH2 refined with riding coordinates:
 N30(H30A,H30B)
2.f Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C15(H15A,H15B,H15C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C)
;
_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
N1 N 0.35393(9) 0.36450(19) 0.35646(5) 0.0195(4) Uani 1 1 d . . . . .
C2 C 0.28988(10) 0.4087(2) 0.37409(6) 0.0182(4) Uani 1 1 d . . . . .
C3 C 0.28429(10) 0.5093(2) 0.41376(6) 0.0184(4) Uani 1 1 d . . . . .
N4 N 0.34501(9) 0.5637(2) 0.43452(6) 0.0215(4) Uani 1 1 d . . . . .
C5 C 0.41210(10) 0.5175(2) 0.41612(7) 0.0205(4) Uani 1 1 d . . . . .
H5 H 0.4574 0.5538 0.4300 0.025 Uiso 1 1 calc R . . . .
C6 C 0.41648(10) 0.4199(2) 0.37801(6) 0.0182(4) Uani 1 1 d . . . . .
O7 O 0.22363(7) 0.36497(16) 0.35534(5) 0.0216(3) Uani 1 1 d . . . . .
C8 C 0.22577(11) 0.2724(2) 0.31314(7) 0.0217(4) Uani 1 1 d . . . . .
H8A H 0.2393 0.1622 0.3204 0.026 Uiso 1 1 calc R . . . .
H8B H 0.2638 0.3155 0.2914 0.026 Uiso 1 1 calc R . . . .
C9 C 0.14804(11) 0.2797(2) 0.29142(7) 0.0236(4) Uani 1 1 d . . . . .
H9 H 0.1100 0.2513 0.3157 0.028 Uiso 1 1 calc R . . . .
C10 C 0.13094(13) 0.4450(3) 0.27401(8) 0.0306(5) Uani 1 1 d . . . . .
H10A H 0.1323 0.5187 0.3002 0.046 Uiso 1 1 calc GR . . . .
H10B H 0.0808 0.4468 0.2597 0.046 Uiso 1 1 calc GR . . . .
H10C H 0.1688 0.4758 0.2509 0.046 Uiso 1 1 calc GR . . . .
C11 C 0.14345(14) 0.1593(3) 0.25220(8) 0.0346(5) Uani 1 1 d . . . . .
H11A H 0.1828 0.1813 0.2292 0.052 Uiso 1 1 calc GR . . . .
H11B H 0.0939 0.1659 0.2373 0.052 Uiso 1 1 calc GR . . . .
H11C H 0.1507 0.0535 0.2649 0.052 Uiso 1 1 calc GR . . . .
C12 C 0.48967(11) 0.3681(2) 0.35758(7) 0.0208(4) Uani 1 1 d . . . . .
O13 O 0.49583(8) 0.29000(19) 0.32286(5) 0.0332(4) Uani 1 1 d . . . . .
O14 O 0.54800(7) 0.41890(17) 0.38318(5) 0.0245(3) Uani 1 1 d . . . . .
C15 C 0.62169(11) 0.3736(3) 0.36639(8) 0.0266(5) Uani 1 1 d . . . . .
H15A H 0.6297 0.4181 0.3353 0.040 Uiso 1 1 calc GR . . . .
H15B H 0.6249 0.2587 0.3648 0.040 Uiso 1 1 calc GR . . . .
H15C H 0.6604 0.4134 0.3877 0.040 Uiso 1 1 calc GR . . . .
N16 N 0.21212(9) 0.5472(2) 0.42821(6) 0.0206(4) Uani 1 1 d . . . . .
H16 H 0.1754 0.5044 0.4120 0.025 Uiso 1 1 calc R . . . .
C17 C 0.18995(11) 0.6423(2) 0.46422(7) 0.0208(4) Uani 1 1 d . . . . .
O18 O 0.23422(8) 0.70755(18) 0.49061(5) 0.0301(4) Uani 1 1 d . . . . .
N19 N 0.06320(9) 0.58082(19) 0.43720(5) 0.0188(3) Uani 1 1 d . . . . .
C20 C -0.00861(10) 0.5993(2) 0.44183(6) 0.0184(4) Uani 1 1 d . . . . .
C21 C -0.04159(10) 0.6962(2) 0.47805(7) 0.0197(4) Uani 1 1 d . . . . .
N22 N 0.00271(9) 0.7708(2) 0.50786(6) 0.0220(4) Uani 1 1 d . . . . .
C23 C 0.07715(11) 0.7516(3) 0.50266(7) 0.0220(4) Uani 1 1 d . . . . .
H23 H 0.1101 0.8043 0.5235 0.026 Uiso 1 1 calc R . . . .
C24 C 0.10783(10) 0.6589(2) 0.46850(7) 0.0198(4) Uani 1 1 d . . . . .
O25 O -0.05917(7) 0.53119(17) 0.41308(5) 0.0226(3) Uani 1 1 d . . . . .
C26 C -0.03058(11) 0.4299(2) 0.37671(7) 0.0239(4) Uani 1 1 d . . . . .
H26A H -0.0076 0.3345 0.3904 0.029 Uiso 1 1 calc R . . . .
H26B H 0.0083 0.4856 0.3583 0.029 Uiso 1 1 calc R . . . .
C27 C -0.09645(12) 0.3855(3) 0.34592(8) 0.0291(5) Uani 1 1 d . . . . .
H27 H -0.1182 0.4842 0.3326 0.035 Uiso 1 1 calc R . . . .
C28 C -0.15739(15) 0.3026(4) 0.37297(10) 0.0484(7) Uani 1 1 d . . . . .
H28A H -0.1977 0.2704 0.3517 0.073 Uiso 1 1 calc GR . . . .
H28B H -0.1779 0.3739 0.3966 0.073 Uiso 1 1 calc GR . . . .
H28C H -0.1362 0.2095 0.3882 0.073 Uiso 1 1 calc GR . . . .
C29 C -0.06812(14) 0.2837(3) 0.30564(8) 0.0354(5) Uani 1 1 d . . . . .
H29A H -0.0305 0.3425 0.2877 0.053 Uiso 1 1 calc GR . . . .
H29B H -0.1105 0.2560 0.2854 0.053 Uiso 1 1 calc GR . . . .
H29C H -0.0452 0.1876 0.3180 0.053 Uiso 1 1 calc GR . . . .
N30 N -0.11630(9) 0.7103(2) 0.48116(6) 0.0240(4) Uani 1 1 d . . . . .
H30A H -0.1363 0.7693 0.5031 0.029 Uiso 1 1 calc R . . . .
H30B H -0.1456 0.6605 0.4613 0.029 Uiso 1 1 calc R . . . .
O31 O 0.24100(14) 0.9499(3) 0.55439(8) 0.0623(6) Uani 1 1 d . . . . .
H31A H 0.2265 0.8840 0.5340 0.093 Uiso 1 1 d G . . . .
H31B H 0.2463 1.0397 0.5418 0.093 Uiso 1 1 d G . . . .


_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
N1 C2 1.300(2) . ?
N1 C6 1.356(2) . ?
C2 C3 1.429(3) . ?
C2 O7 1.346(2) . ?
C3 N4 1.316(2) . ?
C3 N16 1.385(2) . ?
N4 C5 1.361(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.377(3) . ?
C6 C12 1.492(3) . ?
O7 C8 1.447(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.516(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.523(3) . ?
C9 C11 1.525(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O13 1.204(2) . ?
C12 O14 1.342(2) . ?
O14 C15 1.446(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N16 H16 0.8800 . ?
N16 C17 1.372(3) . ?
C17 O18 1.225(2) . ?
C17 C24 1.469(3) . ?
N19 C20 1.291(2) . ?
N19 C24 1.371(2) . ?
C20 C21 1.451(3) . ?
C20 O25 1.351(2) . ?
C21 N22 1.325(3) . ?
C21 N30 1.334(2) . ?
N22 C23 1.339(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.372(3) . ?
O25 C26 1.447(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.515(3) . ?
C27 H27 1.0000 . ?
C27 C28 1.507(3) . ?
C27 C29 1.531(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
N30 H30A 0.8800 . ?
N30 H30B 0.8800 . ?
O31 H31A 0.8498 . ?
O31 H31B 0.8500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 115.92(16) . . ?
N1 C2 C3 123.01(17) . . ?
N1 C2 O7 121.85(17) . . ?
O7 C2 C3 115.12(16) . . ?
N4 C3 C2 121.05(17) . . ?
N4 C3 N16 122.63(17) . . ?
N16 C3 C2 116.32(16) . . ?
C3 N4 C5 116.01(17) . . ?
N4 C5 H5 118.9 . . ?
N4 C5 C6 122.20(17) . . ?
C6 C5 H5 118.9 . . ?
N1 C6 C5 121.81(17) . . ?
N1 C6 C12 115.48(16) . . ?
C5 C6 C12 122.71(17) . . ?
C2 O7 C8 117.60(14) . . ?
O7 C8 H8A 110.2 . . ?
O7 C8 H8B 110.2 . . ?
O7 C8 C9 107.43(15) . . ?
H8A C8 H8B 108.5 . . ?
C9 C8 H8A 110.2 . . ?
C9 C8 H8B 110.2 . . ?
C8 C9 H9 108.5 . . ?
C8 C9 C10 110.76(17) . . ?
C8 C9 C11 109.02(17) . . ?
C10 C9 H9 108.5 . . ?
C10 C9 C11 111.46(17) . . ?
C11 C9 H9 108.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O13 C12 C6 124.62(18) . . ?
O13 C12 O14 124.23(18) . . ?
O14 C12 C6 111.14(16) . . ?
C12 O14 C15 115.39(15) . . ?
O14 C15 H15A 109.5 . . ?
O14 C15 H15B 109.5 . . ?
O14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C3 N16 H16 115.5 . . ?
C17 N16 C3 129.01(16) . . ?
C17 N16 H16 115.5 . . ?
N16 C17 C24 113.85(16) . . ?
O18 C17 N16 123.41(17) . . ?
O18 C17 C24 122.74(17) . . ?
C20 N19 C24 116.34(16) . . ?
N19 C20 C21 122.77(17) . . ?
N19 C20 O25 122.71(17) . . ?
O25 C20 C21 114.51(16) . . ?
N22 C21 C20 119.80(17) . . ?
N22 C21 N30 120.21(17) . . ?
N30 C21 C20 119.99(17) . . ?
C21 N22 C23 117.02(17) . . ?
N22 C23 H23 118.6 . . ?
N22 C23 C24 122.80(18) . . ?
C24 C23 H23 118.6 . . ?
N19 C24 C17 118.15(17) . . ?
N19 C24 C23 121.27(17) . . ?
C23 C24 C17 120.58(17) . . ?
C20 O25 C26 117.70(15) . . ?
O25 C26 H26A 110.2 . . ?
O25 C26 H26B 110.2 . . ?
O25 C26 C27 107.49(16) . . ?
H26A C26 H26B 108.5 . . ?
C27 C26 H26A 110.2 . . ?
C27 C26 H26B 110.2 . . ?
C26 C27 H27 108.2 . . ?
C26 C27 C29 109.26(18) . . ?
C28 C27 C26 111.6(2) . . ?
C28 C27 H27 108.2 . . ?
C28 C27 C29 111.21(19) . . ?
C29 C27 H27 108.2 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C21 N30 H30A 120.0 . . ?
C21 N30 H30B 120.0 . . ?
H30A N30 H30B 120.0 . . ?
H31A O31 H31B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N4 0.4(3) . . . . ?
N1 C2 C3 N16 179.39(17) . . . . ?
N1 C2 O7 C8 -2.9(3) . . . . ?
N1 C6 C12 O13 4.2(3) . . . . ?
N1 C6 C12 O14 -175.34(16) . . . . ?
C2 N1 C6 C5 -0.2(3) . . . . ?
C2 N1 C6 C12 179.81(16) . . . . ?
C2 C3 N4 C5 -0.4(3) . . . . ?
C2 C3 N16 C17 -178.75(18) . . . . ?
C2 O7 C8 C9 -163.40(16) . . . . ?
C3 C2 O7 C8 175.65(16) . . . . ?
C3 N4 C5 C6 0.1(3) . . . . ?
C3 N16 C17 O18 -1.7(3) . . . . ?
C3 N16 C17 C24 178.42(18) . . . . ?
N4 C3 N16 C17 0.2(3) . . . . ?
N4 C5 C6 N1 0.2(3) . . . . ?
N4 C5 C6 C12 -179.84(18) . . . . ?
C5 C6 C12 O13 -175.8(2) . . . . ?
C5 C6 C12 O14 4.7(3) . . . . ?
C6 N1 C2 C3 -0.1(3) . . . . ?
C6 N1 C2 O7 178.41(16) . . . . ?
C6 C12 O14 C15 179.56(16) . . . . ?
O7 C2 C3 N4 -178.15(17) . . . . ?
O7 C2 C3 N16 0.8(3) . . . . ?
O7 C8 C9 C10 67.7(2) . . . . ?
O7 C8 C9 C11 -169.26(17) . . . . ?
O13 C12 O14 C15 0.0(3) . . . . ?
N16 C3 N4 C5 -179.33(17) . . . . ?
N16 C17 C24 N19 -0.1(3) . . . . ?
N16 C17 C24 C23 -179.41(18) . . . . ?
O18 C17 C24 N19 -179.93(19) . . . . ?
O18 C17 C24 C23 0.7(3) . . . . ?
N19 C20 C21 N22 0.5(3) . . . . ?
N19 C20 C21 N30 -179.76(18) . . . . ?
N19 C20 O25 C26 1.9(3) . . . . ?
C20 N19 C24 C17 -179.44(17) . . . . ?
C20 N19 C24 C23 -0.1(3) . . . . ?
C20 C21 N22 C23 -0.2(3) . . . . ?
C20 O25 C26 C27 -172.94(17) . . . . ?
C21 C20 O25 C26 -178.62(16) . . . . ?
C21 N22 C23 C24 -0.3(3) . . . . ?
N22 C23 C24 C17 179.76(19) . . . . ?
N22 C23 C24 N19 0.4(3) . . . . ?
C24 N19 C20 C21 -0.3(3) . . . . ?
C24 N19 C20 O25 179.06(17) . . . . ?
O25 C20 C21 N22 -178.94(17) . . . . ?
O25 C20 C21 N30 0.8(3) . . . . ?
O25 C26 C27 C28 -59.0(2) . . . . ?
O25 C26 C27 C29 177.60(17) . . . . ?
N30 C21 N22 C23 -179.91(18) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_original_sample_id PG20
_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 1.360
_oxdiff_exptl_absorpt_empirical_full_min 0.677
####################################################################### 
# 
# 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_wdb1004
_database_code_depnum_ccdc_archive 'CCDC 1512414'
_audit_update_record             
;
2016-10-27 deposited with the CCDC.
2016-11-29 downloaded from the CCDC.
;
_audit_creation_date             2016-06-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;


_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H17 N5 O2'
_chemical_formula_sum            'C11 H17 N5 O2'
_chemical_formula_weight         251.29
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C31 H35 N9 O7'
_chemical_oxdiff_usercomment     PG36
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   12.7749(11)
_cell_length_b                   10.4901(10)
_cell_length_c                   9.5080(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1274.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2462
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.6490
_cell_measurement_theta_min      2.6590
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (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    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7542
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         2.512
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_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    -20.00  25.00   1.00    5.00    --  -17.00 -99.00-120.00   45
  2  ω    -86.00   4.00   1.00    5.00    --  -17.00 -57.00  30.00   90
  3  ω    -50.00  40.00   1.00    5.00    --   19.03 -57.00-120.00   90
  4  ω    -47.00  37.00   1.00    5.00    --  -17.00  77.00  30.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0099402000
_diffrn_orient_matrix_UB_12      -0.0191859000
_diffrn_orient_matrix_UB_13      -0.0702035000
_diffrn_orient_matrix_UB_21      0.0035037000
_diffrn_orient_matrix_UB_22      0.0644148000
_diffrn_orient_matrix_UB_23      -0.0224421000
_diffrn_orient_matrix_UB_31      0.0545117000
_diffrn_orient_matrix_UB_32      -0.0075619000
_diffrn_orient_matrix_UB_33      -0.0114071000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2198
_reflns_number_total             2589
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         0.128
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 786 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2589
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.064
_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)+(0.0418P)²+0.1419P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0945
_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,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5)
2.c X=CH2 refined with riding coordinates:
 N9(H9A,H9B)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C18(H18A,H18B,H18C)
;
_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
N1 N 0.37561(15) 0.90966(19) 0.0518(2) 0.0294(5) Uani 1 1 d . . . . .
C2 C 0.42030(17) 0.7981(2) 0.0529(3) 0.0274(5) Uani 1 1 d . . . . .
C3 C 0.38521(18) 0.6923(2) -0.0287(3) 0.0282(5) Uani 1 1 d . . . . .
N4 N 0.30252(16) 0.70556(19) -0.1115(3) 0.0335(5) Uani 1 1 d . . . . .
C5 C 0.2551(2) 0.8220(2) -0.1120(3) 0.0351(6) Uani 1 1 d . . . . .
H5 H 0.1952 0.8341 -0.1697 0.042 Uiso 1 1 calc R . . . .
C6 C 0.29026(17) 0.9220(2) -0.0325(3) 0.0298(6) Uani 1 1 d . . . . .
O7 O 0.50576(13) 0.77629(16) 0.1336(2) 0.0344(4) Uani 1 1 d . . . . .
C8 C 0.5413(2) 0.8833(3) 0.2151(3) 0.0410(7) Uani 1 1 d . . . . .
H8A H 0.5507 0.9572 0.1533 0.062 Uiso 1 1 calc GR . . . .
H8B H 0.6082 0.8622 0.2600 0.062 Uiso 1 1 calc GR . . . .
H8C H 0.4893 0.9035 0.2875 0.062 Uiso 1 1 calc GR . . . .
N9 N 0.43444(15) 0.5792(2) -0.0201(2) 0.0338(5) Uani 1 1 d . . . . .
H9A H 0.4117 0.5139 -0.0695 0.041 Uiso 1 1 calc R . . . .
H9B H 0.4894 0.5705 0.0350 0.041 Uiso 1 1 calc R . . . .
C10 C 0.23195(18) 1.0460(2) -0.0332(3) 0.0319(6) Uani 1 1 d . . . . .
O11 O 0.13541(13) 1.04539(16) -0.0354(2) 0.0433(5) Uani 1 1 d . . . . .
N12 N 0.28696(15) 1.15623(18) -0.0295(3) 0.0364(6) Uani 1 1 d . . . . .
C13 C 0.39825(19) 1.1709(2) -0.0627(4) 0.0429(8) Uani 1 1 d . . . . .
H13A H 0.4315 1.0859 -0.0692 0.051 Uiso 1 1 calc R . . . .
H13B H 0.4333 1.2191 0.0134 0.051 Uiso 1 1 calc R . . . .
C14 C 0.4114(2) 1.2406(2) -0.2000(3) 0.0424(8) Uani 1 1 d . . . . .
H14A H 0.4869 1.2533 -0.2190 0.051 Uiso 1 1 calc R . . . .
H14B H 0.3819 1.1884 -0.2772 0.051 Uiso 1 1 calc R . . . .
N15 N 0.35908(17) 1.36383(19) -0.1968(2) 0.0326(5) Uani 1 1 d . . . . .
C16 C 0.2476(2) 1.3468(3) -0.1658(3) 0.0396(7) Uani 1 1 d . . . . .
H16A H 0.2144 1.2972 -0.2422 0.048 Uiso 1 1 calc R . . . .
H16B H 0.2130 1.4311 -0.1612 0.048 Uiso 1 1 calc R . . . .
C17 C 0.23288(19) 1.2785(2) -0.0287(3) 0.0362(6) Uani 1 1 d . . . . .
H17A H 0.2604 1.3318 0.0489 0.043 Uiso 1 1 calc R . . . .
H17B H 0.1573 1.2645 -0.0120 0.043 Uiso 1 1 calc R . . . .
C18 C 0.3728(3) 1.4315(3) -0.3294(3) 0.0549(9) Uani 1 1 d . . . . .
H18A H 0.4477 1.4404 -0.3496 0.082 Uiso 1 1 calc GR . . . .
H18B H 0.3409 1.5162 -0.3225 0.082 Uiso 1 1 calc GR . . . .
H18C H 0.3392 1.3835 -0.4053 0.082 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
N1 C2 1.302(3) . ?
N1 C6 1.359(3) . ?
C2 C3 1.426(3) . ?
C2 O7 1.354(3) . ?
C3 N4 1.325(3) . ?
C3 N9 1.345(3) . ?
N4 C5 1.363(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.369(4) . ?
C6 C10 1.499(3) . ?
O7 C8 1.437(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?
C10 O11 1.234(3) . ?
C10 N12 1.353(3) . ?
N12 C13 1.464(3) . ?
N12 C17 1.457(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.506(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 N15 1.455(3) . ?
N15 C16 1.465(3) . ?
N15 C18 1.458(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.499(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 116.2(2) . . ?
N1 C2 C3 123.9(2) . . ?
N1 C2 O7 120.7(2) . . ?
O7 C2 C3 115.5(2) . . ?
N4 C3 C2 119.5(2) . . ?
N4 C3 N9 120.1(2) . . ?
N9 C3 C2 120.4(2) . . ?
C3 N4 C5 116.8(2) . . ?
N4 C5 H5 118.7 . . ?
N4 C5 C6 122.6(2) . . ?
C6 C5 H5 118.7 . . ?
N1 C6 C5 121.0(2) . . ?
N1 C6 C10 118.9(2) . . ?
C5 C6 C10 120.0(2) . . ?
C2 O7 C8 115.35(19) . . ?
O7 C8 H8A 109.5 . . ?
O7 C8 H8B 109.5 . . ?
O7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 N9 H9A 120.0 . . ?
C3 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
O11 C10 C6 119.5(2) . . ?
O11 C10 N12 121.6(2) . . ?
N12 C10 C6 118.90(19) . . ?
C10 N12 C13 126.1(2) . . ?
C10 N12 C17 120.39(19) . . ?
C17 N12 C13 111.64(19) . . ?
N12 C13 H13A 109.6 . . ?
N12 C13 H13B 109.6 . . ?
N12 C13 C14 110.2(2) . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N15 C14 C13 111.2(2) . . ?
N15 C14 H14A 109.4 . . ?
N15 C14 H14B 109.4 . . ?
C14 N15 C16 110.00(19) . . ?
C14 N15 C18 111.0(2) . . ?
C18 N15 C16 110.5(2) . . ?
N15 C16 H16A 109.5 . . ?
N15 C16 H16B 109.5 . . ?
N15 C16 C17 110.8(2) . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
N12 C17 C16 110.9(2) . . ?
N12 C17 H17A 109.5 . . ?
N12 C17 H17B 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 108.0 . . ?
N15 C18 H18A 109.5 . . ?
N15 C18 H18B 109.5 . . ?
N15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N4 0.1(4) . . . . ?
N1 C2 C3 N9 -178.8(2) . . . . ?
N1 C2 O7 C8 0.0(3) . . . . ?
N1 C6 C10 O11 -138.8(3) . . . . ?
N1 C6 C10 N12 40.3(4) . . . . ?
C2 N1 C6 C5 -0.6(4) . . . . ?
C2 N1 C6 C10 177.0(2) . . . . ?
C2 C3 N4 C5 -0.6(4) . . . . ?
C3 C2 O7 C8 179.7(2) . . . . ?
C3 N4 C5 C6 0.5(4) . . . . ?
N4 C5 C6 N1 0.1(4) . . . . ?
N4 C5 C6 C10 -177.5(2) . . . . ?
C5 C6 C10 O11 38.8(4) . . . . ?
C5 C6 C10 N12 -142.1(3) . . . . ?
C6 N1 C2 C3 0.5(3) . . . . ?
C6 N1 C2 O7 -179.9(2) . . . . ?
C6 C10 N12 C13 17.7(4) . . . . ?
C6 C10 N12 C17 -179.4(3) . . . . ?
O7 C2 C3 N4 -179.5(2) . . . . ?
O7 C2 C3 N9 1.6(3) . . . . ?
N9 C3 N4 C5 178.3(2) . . . . ?
C10 N12 C13 C14 109.0(3) . . . . ?
C10 N12 C17 C16 -109.6(3) . . . . ?
O11 C10 N12 C13 -163.2(3) . . . . ?
O11 C10 N12 C17 -0.3(4) . . . . ?
N12 C13 C14 N15 56.6(3) . . . . ?
C13 N12 C17 C16 55.6(3) . . . . ?
C13 C14 N15 C16 -57.9(3) . . . . ?
C13 C14 N15 C18 179.4(2) . . . . ?
C14 N15 C16 C17 57.6(3) . . . . ?
N15 C16 C17 N12 -56.6(3) . . . . ?
C17 N12 C13 C14 -55.2(3) . . . . ?
C18 N15 C16 C17 -179.4(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-06-07
_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 1.307
_oxdiff_exptl_absorpt_empirical_full_min 0.856
