# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_str1737
_database_code_depnum_ccdc_archive 'CCDC 1880517'
loop_
_audit_author_name
_audit_author_address
'Vicente Mart? Centelles'
;Universitat Jaume I
Spain
;
_audit_update_record             
;
2018-11-21 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_EXPT005_str1737             
;
PROBLEM: _exptl_crystal_description is missing
RESPONSE: No description was provided.
;
# Added during the CSD deposition process: Wednesday 21 November 2018 05:31 PM
# end Validation Reply Form

_audit_creation_date             2015-11-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H26 N4 O2, 2(H2 O)'
_chemical_formula_sum            'C12 H30 N4 O4'
_chemical_formula_weight         294.40
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H26 N4 O2'
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                   12.5640(3)
_cell_length_b                   4.80981(7)
_cell_length_c                   15.8319(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.756(3)
_cell_angle_gamma                90
_cell_volume                     882.26(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5235
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.2740
_cell_measurement_theta_min      5.6860
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.108
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.3977
_exptl_crystal_size_mid          0.1078
_exptl_crystal_size_min          0.0509
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8173
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        65.999
_diffrn_reflns_theta_max         65.999
_diffrn_reflns_theta_min         3.815
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4051
_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 -116.00  -14.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -37.0000  -60.0000 204

#__ type_ start__ end____ width___ exp.time_
  2 omega  -70.00   34.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680   57.0000  150.0000 208

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   82.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.0680  -99.0000  -90.0000 162

#__ type_ start__ end____ width___ exp.time_
  4 omega   31.00  122.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400 -125.0000  -90.0000 182

#__ type_ start__ end____ width___ exp.time_
  5 omega   28.00   91.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -30.0000   90.0000 126

#__ type_ start__ end____ width___ exp.time_
  6 omega   27.00  139.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -77.0000  -60.0000 224

#__ type_ start__ end____ width___ exp.time_
  7 omega   28.00   91.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -30.0000    0.0000 126

#__ type_ start__ end____ width___ exp.time_
  8 omega   28.00   91.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -30.0000 -180.0000 126

#__ type_ start__ end____ width___ exp.time_
  9 omega   28.00   91.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -30.0000  -60.0000 126

#__ type_ start__ end____ width___ exp.time_
 10 omega   44.00  178.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400   15.0000   90.0000 268

#__ type_ start__ end____ width___ exp.time_
 11 omega -119.00   -6.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -77.0000  -90.0000 226

#__ type_ start__ end____ width___ exp.time_
 12 omega -114.00  -10.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -57.0000   60.0000 208

#__ type_ start__ end____ width___ exp.time_
 13 omega -114.00  -10.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -57.0000 -180.0000 208

#__ type_ start__ end____ width___ exp.time_
 14 omega   75.00  178.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400   61.0000  -30.0000 206

#__ type_ start__ end____ width___ exp.time_
 15 omega   75.00  178.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400   30.0000 -180.0000 206

#__ type_ start__ end____ width___ exp.time_
 16 omega   21.00  108.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -94.0000  120.0000 174

#__ type_ start__ end____ width___ exp.time_
 17 omega   72.00  104.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400   77.0000 -180.0000 64

#__ type_ start__ end____ width___ exp.time_
 18 omega   75.00  178.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400   61.0000  120.0000 206

#__ type_ start__ end____ width___ exp.time_
 19 omega   75.00  178.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400   30.0000  -90.0000 206
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0529811000
_diffrn_orient_matrix_UB_12      -0.2936589000
_diffrn_orient_matrix_UB_13      -0.0149187000
_diffrn_orient_matrix_UB_21      0.0085236000
_diffrn_orient_matrix_UB_22      -0.0040824000
_diffrn_orient_matrix_UB_23      0.0997152000
_diffrn_orient_matrix_UB_31      -0.1216726000
_diffrn_orient_matrix_UB_32      0.1277475000
_diffrn_orient_matrix_UB_33      -0.0311505000
_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_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                2835
_reflns_number_total             3066
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1132 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3066
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.078
_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)+(0.0822P)²+0.0244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1244
_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,H) groups
2. Restrained distances
 N3-H3 = N2-H2 = N4-H4A = N4-H4B = N1-H1A = N1-H1B
 0.97 with sigma of 0.02
3.a Free rotating group:
 O3(H3A,H3B), O4(H4C,H4D)
3.b Ternary CH refined with riding coordinates:
 C9(H9), C4(H4), C5(H5), C10(H10)
3.c Secondary CH2 refined with riding coordinates:
 C1(H1C,H1D), C2(H2A,H2B)
3.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C6(H6A,H6B,H6C), C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.55306(19) 0.3712(4) 0.40363(14) 0.0364(5) Uani 1 1 d . . . . .
O2 O 0.3204(2) 1.0054(4) 0.05822(17) 0.0461(6) Uani 1 1 d . . . . .
O3 O 0.0860(2) 0.7655(5) 0.13913(13) 0.0391(5) Uani 1 1 d . . . . .
H3A H 0.1145 0.6254 0.1731 0.059 Uiso 1 1 d G . . . .
H3B H 0.0903 0.7414 0.0874 0.059 Uiso 1 1 d G . . . .
N3 N 0.3624(2) 0.5657(4) 0.10699(15) 0.0262(5) Uani 1 1 d D . . . .
C3 C 0.5753(2) 0.6236(5) 0.40989(16) 0.0232(5) Uani 1 1 d . . . . .
N2 N 0.51205(19) 0.8086(4) 0.34867(14) 0.0233(5) Uani 1 1 d D . . . .
O4 O 0.1797(2) 0.2630(5) 0.23010(14) 0.0472(6) Uani 1 1 d . . . . .
H4C H 0.1537 0.1085 0.2043 0.071 Uiso 1 1 d G . . . .
H4D H 0.2100 0.2401 0.2878 0.071 Uiso 1 1 d G . . . .
C8 C 0.3012(2) 0.7543(6) 0.04675(17) 0.0253(5) Uani 1 1 d . . . . .
N4 N 0.0961(2) 0.7495(6) -0.03670(15) 0.0340(5) Uani 1 1 d D . . . .
N1 N 0.6755(2) 0.6410(6) 0.57742(15) 0.0344(6) Uani 1 1 d D . . . .
C9 C 0.2051(2) 0.6474(5) -0.03921(16) 0.0250(5) Uani 1 1 d . . . . .
H9 H 0.2048 0.4439 -0.0364 0.030 Uiso 1 1 calc R . . . .
C4 C 0.6795(2) 0.7331(5) 0.49055(16) 0.0251(5) Uani 1 1 d . . . . .
H4 H 0.6773 0.9367 0.4889 0.030 Uiso 1 1 calc R . . . .
C1 C 0.4146(2) 0.7308(5) 0.26534(16) 0.0259(5) Uani 1 1 d . . . . .
H1C H 0.3626 0.8877 0.2437 0.031 Uiso 1 1 calc R . . . .
H1D H 0.3724 0.5793 0.2785 0.031 Uiso 1 1 calc R . . . .
C2 C 0.4567(2) 0.6418(6) 0.19164(17) 0.0291(6) Uani 1 1 d . . . . .
H2A H 0.5001 0.7928 0.1797 0.035 Uiso 1 1 calc R . . . .
H2B H 0.5083 0.4843 0.2136 0.035 Uiso 1 1 calc R . . . .
C5 C 0.7913(2) 0.6369(7) 0.48162(18) 0.0351(6) Uani 1 1 d . . . . .
H5 H 0.7941 0.4334 0.4850 0.042 Uiso 1 1 calc R . . . .
C10 C 0.2271(3) 0.7334(6) -0.12466(18) 0.0345(6) Uani 1 1 d . . . . .
H10 H 0.2301 0.9369 -0.1261 0.041 Uiso 1 1 calc R . . . .
C7 C 0.8970(3) 0.7497(12) 0.5591(2) 0.0584(10) Uani 1 1 d . . . . .
H7A H 0.8952 0.9492 0.5577 0.088 Uiso 1 1 calc GR . . . .
H7B H 0.9654 0.6856 0.5519 0.088 Uiso 1 1 calc GR . . . .
H7C H 0.8974 0.6857 0.6166 0.088 Uiso 1 1 calc GR . . . .
C6 C 0.7938(3) 0.7235(11) 0.3900(2) 0.0594(11) Uani 1 1 d . . . . .
H6A H 0.7348 0.6253 0.3415 0.089 Uiso 1 1 calc GR . . . .
H6B H 0.8678 0.6800 0.3890 0.089 Uiso 1 1 calc GR . . . .
H6C H 0.7802 0.9199 0.3816 0.089 Uiso 1 1 calc GR . . . .
C12 C 0.1298(3) 0.6363(10) -0.2116(2) 0.0556(10) Uani 1 1 d . . . . .
H12A H 0.1205 0.4388 -0.2089 0.083 Uiso 1 1 calc GR . . . .
H12B H 0.1480 0.6809 -0.2636 0.083 Uiso 1 1 calc GR . . . .
H12C H 0.0594 0.7276 -0.2172 0.083 Uiso 1 1 calc GR . . . .
C11 C 0.3424(3) 0.6211(10) -0.1200(3) 0.0564(9) Uani 1 1 d . . . . .
H11A H 0.4035 0.6988 -0.0678 0.085 Uiso 1 1 calc GR . . . .
H11B H 0.3533 0.6714 -0.1748 0.085 Uiso 1 1 calc GR . . . .
H11C H 0.3431 0.4223 -0.1146 0.085 Uiso 1 1 calc GR . . . .
H2 H 0.534(3) 0.995(5) 0.361(2) 0.038(9) Uiso 1 1 d D . . . .
H4A H 0.033(3) 0.645(8) -0.079(2) 0.043(9) Uiso 1 1 d D . . . .
H3 H 0.344(3) 0.376(5) 0.094(3) 0.045(10) Uiso 1 1 d D . . . .
H1A H 0.671(4) 0.444(5) 0.576(3) 0.057(12) Uiso 1 1 d D . . . .
H1B H 0.608(3) 0.706(9) 0.584(3) 0.054(11) Uiso 1 1 d D . . . .
H4B H 0.085(4) 0.941(6) -0.055(3) 0.066(13) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.241(3) . ?
O2 C8 1.231(4) . ?
O3 H3A 0.8500 . ?
O3 H3B 0.8499 . ?
N3 C8 1.325(4) . ?
N3 C2 1.451(3) . ?
N3 H3 0.94(2) . ?
C3 N2 1.329(3) . ?
C3 C4 1.526(3) . ?
N2 C1 1.459(3) . ?
N2 H2 0.94(2) . ?
O4 H4C 0.8501 . ?
O4 H4D 0.8497 . ?
C8 C9 1.518(3) . ?
N4 C9 1.469(4) . ?
N4 H4A 0.96(2) . ?
N4 H4B 0.96(3) . ?
N1 C4 1.464(3) . ?
N1 H1A 0.95(3) . ?
N1 H1B 0.94(2) . ?
C9 H9 0.9800 . ?
C9 C10 1.539(3) . ?
C4 H4 0.9800 . ?
C4 C5 1.536(4) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C1 C2 1.517(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5 H5 0.9800 . ?
C5 C7 1.517(5) . ?
C5 C6 1.521(4) . ?
C10 H10 0.9800 . ?
C10 C12 1.518(4) . ?
C10 C11 1.521(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H3A O3 H3B 109.5 . . ?
C8 N3 C2 122.1(2) . . ?
C8 N3 H3 119(3) . . ?
C2 N3 H3 119(3) . . ?
O1 C3 N2 122.9(2) . . ?
O1 C3 C4 119.9(2) . . ?
N2 C3 C4 117.2(2) . . ?
C3 N2 C1 122.9(2) . . ?
C3 N2 H2 116(2) . . ?
C1 N2 H2 121(2) . . ?
H4C O4 H4D 109.5 . . ?
O2 C8 N3 122.6(3) . . ?
O2 C8 C9 120.5(2) . . ?
N3 C8 C9 116.9(2) . . ?
C9 N4 H4A 109(2) . . ?
C9 N4 H4B 110(3) . . ?
H4A N4 H4B 108(4) . . ?
C4 N1 H1A 108(3) . . ?
C4 N1 H1B 111(3) . . ?
H1A N1 H1B 107(4) . . ?
C8 C9 H9 108.2 . . ?
C8 C9 C10 110.2(2) . . ?
N4 C9 C8 106.82(19) . . ?
N4 C9 H9 108.2 . . ?
N4 C9 C10 114.9(2) . . ?
C10 C9 H9 108.2 . . ?
C3 C4 H4 108.4 . . ?
C3 C4 C5 109.7(2) . . ?
N1 C4 C3 110.6(2) . . ?
N1 C4 H4 108.4 . . ?
N1 C4 C5 111.1(2) . . ?
C5 C4 H4 108.4 . . ?
N2 C1 H1C 109.6 . . ?
N2 C1 H1D 109.6 . . ?
N2 C1 C2 110.3(2) . . ?
H1C C1 H1D 108.1 . . ?
C2 C1 H1C 109.6 . . ?
C2 C1 H1D 109.6 . . ?
N3 C2 C1 112.3(2) . . ?
N3 C2 H2A 109.2 . . ?
N3 C2 H2B 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C5 H5 108.1 . . ?
C7 C5 C4 111.3(2) . . ?
C7 C5 H5 108.1 . . ?
C7 C5 C6 109.8(3) . . ?
C6 C5 C4 111.2(2) . . ?
C6 C5 H5 108.1 . . ?
C9 C10 H10 108.1 . . ?
C12 C10 C9 111.0(2) . . ?
C12 C10 H10 108.1 . . ?
C12 C10 C11 110.6(3) . . ?
C11 C10 C9 110.8(3) . . ?
C11 C10 H10 108.1 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
O1 C3 N2 C1 -3.9(4) . . . . ?
O1 C3 C4 N1 -53.3(3) . . . . ?
O1 C3 C4 C5 69.6(3) . . . . ?
O2 C8 C9 N4 -65.1(3) . . . . ?
O2 C8 C9 C10 60.3(3) . . . . ?
N3 C8 C9 N4 115.4(2) . . . . ?
N3 C8 C9 C10 -119.2(3) . . . . ?
C3 N2 C1 C2 -82.3(3) . . . . ?
C3 C4 C5 C7 178.1(3) . . . . ?
C3 C4 C5 C6 55.4(3) . . . . ?
N2 C3 C4 N1 126.8(2) . . . . ?
N2 C3 C4 C5 -110.3(3) . . . . ?
N2 C1 C2 N3 -179.3(2) . . . . ?
C8 N3 C2 C1 81.3(3) . . . . ?
C8 C9 C10 C12 -178.2(3) . . . . ?
C8 C9 C10 C11 58.5(3) . . . . ?
N4 C9 C10 C12 -57.5(4) . . . . ?
N4 C9 C10 C11 179.2(3) . . . . ?
N1 C4 C5 C7 -59.2(4) . . . . ?
N1 C4 C5 C6 178.0(3) . . . . ?
C4 C3 N2 C1 176.0(2) . . . . ?
C2 N3 C8 O2 0.3(4) . . . . ?
C2 N3 C8 C9 179.9(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
8 0 -1 0.0371 8.0050 -0.0031 -1.0027 -0.4082 -0.0317 -0.9431
-8 0 1 0.0371 -8.0050 0.0031 1.0027 0.4082 0.0317 0.9431
1 3 0 0.1773 1.0064 2.9978 0.0015 -0.9337 -0.0035 0.2605
0 -3 0 0.2133 -0.0058 -2.9982 -0.0018 0.8808 0.0120 -0.3822
8 0 -6 0.0306 8.0054 -0.0026 -6.0035 -0.3338 -0.5304 -0.7874
-8 0 7 0.0164 -8.0055 0.0025 7.0037 0.3189 0.6301 0.7562
7 1 -8 0.0638 7.0069 0.9974 -8.0030 -0.5447 -0.7424 -0.4758
-2 0 -8 0.0617 -2.0005 0.0016 -8.0007 0.2249 -0.8149 0.4928
2 0 8 0.0461 2.0005 -0.0016 8.0007 -0.2249 0.8149 -0.4928
6 -1 -8 0.1138 6.0024 -1.0009 -8.0038 0.0953 -0.7429 -0.6089
-6 0 -3 0.0428 -6.0034 0.0027 -2.9986 0.3620 -0.3502 0.8242

_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_str1754
_database_code_depnum_ccdc_archive 'CCDC 1880520'
loop_
_audit_author_name
_audit_author_address
'Vicente Mart? Centelles'
;Universitat Jaume I
Spain
;
_audit_update_record             
;
2018-11-21 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;
_audit_creation_date             2015-11-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H38 N4 O2, H2 O'
_chemical_formula_sum            'C18 H40 N4 O3'
_chemical_formula_weight         360.54
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H38 N4 O2'
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                   4.84556(10)
_cell_length_b                   20.5154(5)
_cell_length_c                   21.9450(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2181.51(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8687
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.4480
_cell_measurement_theta_min      3.9900
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.596
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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    1.098
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.383
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19233
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        65.997
_diffrn_reflns_theta_max         65.997
_diffrn_reflns_theta_min         4.029
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4051
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -120.00    1.10   0.7000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -35.3768  -38.0000   30.0000 173

#__ type_ start__ end____ width___ exp.time_
  2 omega -124.00  -79.90   0.7000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -35.3768  -99.0000  -60.0000 63

#__ type_ start__ end____ width___ exp.time_
  3 omega -124.00  -79.90   0.7000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -35.3768  -99.0000  -90.0000 63

#__ type_ start__ end____ width___ exp.time_
  4 omega -124.00  -79.90   0.7000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -35.3768  -99.0000 -150.0000 63

#__ type_ start__ end____ width___ exp.time_
  5 omega   55.00  128.50   0.7000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.3768 -178.0000   30.0000 105

#__ type_ start__ end____ width___ exp.time_
  6 omega   55.00  128.50   0.7000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.3768 -178.0000  -30.0000 105

#__ type_ start__ end____ width___ exp.time_
  7 omega   25.00   97.10   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3563  -45.0000  -30.0000 103

#__ type_ start__ end____ width___ exp.time_
  8 omega   18.00  109.00   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3563  -94.0000   90.0000 130

#__ type_ start__ end____ width___ exp.time_
  9 omega   25.00   97.10   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3563  -45.0000 -120.0000 103

#__ type_ start__ end____ width___ exp.time_
 10 omega  100.00  177.00   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3563  111.0000  120.0000 110

#__ type_ start__ end____ width___ exp.time_
 11 omega   18.00  109.00   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3563  -94.0000   30.0000 130

#__ type_ start__ end____ width___ exp.time_
 12 omega   19.00  177.20   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3563   15.0000    0.0000 226

#__ type_ start__ end____ width___ exp.time_
 13 omega -124.00  -79.90   0.7000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -35.3768  -99.0000   30.0000 63

#__ type_ start__ end____ width___ exp.time_
 14 omega -120.00    0.40   0.7000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -35.3768  -57.0000  -90.0000 172

#__ type_ start__ end____ width___ exp.time_
 15 omega -120.00    0.40   0.7000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -35.3768  -57.0000  150.0000 172

#__ type_ start__ end____ width___ exp.time_
 16 omega -124.00  -79.90   0.7000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -35.3768  -99.0000  120.0000 63

#__ type_ start__ end____ width___ exp.time_
 17 omega -127.00    3.20   0.7000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -35.3768  -77.0000   30.0000 186

#__ type_ start__ end____ width___ exp.time_
 18 omega   57.00  130.50   0.7000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.3768  178.0000 -150.0000 105

#__ type_ start__ end____ width___ exp.time_
 19 omega   23.00  143.40   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3563  -61.0000  120.0000 172

#__ type_ start__ end____ width___ exp.time_
 20 omega   71.00  176.70   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3563   61.0000   30.0000 151

#__ type_ start__ end____ width___ exp.time_
 21 omega   73.00  178.00   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3563   45.0000 -120.0000 150

#__ type_ start__ end____ width___ exp.time_
 22 omega   18.00   70.50   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3563  -94.0000 -120.0000 75

#__ type_ start__ end____ width___ exp.time_
 23 omega   19.00  177.20   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3563   15.0000 -180.0000 226
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0287192000
_diffrn_orient_matrix_UB_12      0.0279812000
_diffrn_orient_matrix_UB_13      -0.0648771000
_diffrn_orient_matrix_UB_21      -0.0142932000
_diffrn_orient_matrix_UB_22      -0.0696643000
_diffrn_orient_matrix_UB_23      -0.0259698000
_diffrn_orient_matrix_UB_31      -0.3161857000
_diffrn_orient_matrix_UB_32      0.0006811000
_diffrn_orient_matrix_UB_33      0.0070924000
_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_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3602
_reflns_number_total             3808
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 1401 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3808
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.042
_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)+(0.0974P)²+0.0815P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1279
_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:
 C15(H15), C10(H10), C16(H16), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C3(H3A,H3B), C6(H6A,H6B), C1(H1A,H1B), C4(H4A,H4B), C5(H5A,H5B),
 C2(H2A,H2B), C8(H8A,H8B)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C17(H17A,H17B,
 H17C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O2 O 0.8934(4) 0.07903(10) 0.24891(8) 0.0436(4) Uani 1 1 d . . . . .
O1 O 0.0445(4) 0.21571(11) 0.80839(8) 0.0455(4) Uani 1 1 d . . . . .
N3 N 0.4614(5) 0.07663(10) 0.28681(8) 0.0342(4) Uani 1 1 d . . . . .
N2 N 0.4829(4) 0.23494(9) 0.78045(8) 0.0303(4) Uani 1 1 d . . . . .
C15 C 0.5207(5) 0.07663(10) 0.17683(9) 0.0304(5) Uani 1 1 d . . . . .
H15 H 0.3191 0.0768 0.1805 0.036 Uiso 1 1 calc R . . . .
C14 C 0.6429(5) 0.07774(10) 0.24108(9) 0.0294(5) Uani 1 1 d . . . . .
C7 C 0.4146(6) 0.12320(12) 0.39067(10) 0.0361(5) Uani 1 1 d . . . . .
H7A H 0.2154 0.1188 0.3893 0.043 Uiso 1 1 calc R . . . .
H7B H 0.4618 0.1661 0.3752 0.043 Uiso 1 1 calc R . . . .
C3 C 0.4063(6) 0.21473(12) 0.60788(9) 0.0367(5) Uani 1 1 d . . . . .
H3A H 0.2061 0.2152 0.6075 0.044 Uiso 1 1 calc R . . . .
H3B H 0.4700 0.2571 0.5941 0.044 Uiso 1 1 calc R . . . .
C9 C 0.2930(5) 0.21298(10) 0.81884(9) 0.0291(4) Uani 1 1 d . . . . .
C6 C 0.5127(6) 0.11711(12) 0.45653(10) 0.0388(5) Uani 1 1 d . . . . .
H6A H 0.4596 0.0746 0.4719 0.047 Uiso 1 1 calc R . . . .
H6B H 0.7126 0.1193 0.4571 0.047 Uiso 1 1 calc R . . . .
C1 C 0.4180(5) 0.25476(11) 0.71819(10) 0.0356(5) Uani 1 1 d . . . . .
H1A H 0.5115 0.2954 0.7090 0.043 Uiso 1 1 calc R . . . .
H1B H 0.2209 0.2620 0.7145 0.043 Uiso 1 1 calc R . . . .
C4 C 0.5096(6) 0.16250(11) 0.56409(9) 0.0389(6) Uani 1 1 d . . . . .
H4A H 0.4575 0.1201 0.5799 0.047 Uiso 1 1 calc R . . . .
H4B H 0.7095 0.1642 0.5629 0.047 Uiso 1 1 calc R . . . .
C10 C 0.3960(5) 0.18328(11) 0.87867(9) 0.0317(5) Uani 1 1 d . . . . .
H10 H 0.5939 0.1922 0.8824 0.038 Uiso 1 1 calc R . . . .
N4 N 0.6021(6) 0.13345(11) 0.14100(10) 0.0426(5) Uani 1 1 d . . . . .
C5 C 0.3999(6) 0.16879(12) 0.49913(9) 0.0392(6) Uani 1 1 d . . . . .
H5A H 0.2001 0.1657 0.4999 0.047 Uiso 1 1 calc R . . . .
H5B H 0.4480 0.2115 0.4834 0.047 Uiso 1 1 calc R . . . .
C2 C 0.5070(6) 0.20305(11) 0.67300(9) 0.0370(5) Uani 1 1 d . . . . .
H2A H 0.4386 0.1611 0.6867 0.044 Uiso 1 1 calc R . . . .
H2B H 0.7070 0.2009 0.6727 0.044 Uiso 1 1 calc R . . . .
C8 C 0.5446(5) 0.07183(13) 0.35054(10) 0.0408(6) Uani 1 1 d . . . . .
H8A H 0.7437 0.0757 0.3531 0.049 Uiso 1 1 calc R . . . .
H8B H 0.4943 0.0291 0.3659 0.049 Uiso 1 1 calc R . . . .
N1 N 0.2543(5) 0.21198(11) 0.93133(8) 0.0385(5) Uani 1 1 d . . . . .
C18 C 0.5066(9) 0.01095(15) 0.07945(12) 0.0622(10) Uani 1 1 d . . . . .
H18A H 0.3098 0.0161 0.0785 0.093 Uiso 1 1 calc GR . . . .
H18B H 0.5555 -0.0301 0.0615 0.093 Uiso 1 1 calc GR . . . .
H18C H 0.5916 0.0456 0.0569 0.093 Uiso 1 1 calc GR . . . .
C16 C 0.6064(6) 0.01288(12) 0.14511(10) 0.0383(5) Uani 1 1 d . . . . .
H16 H 0.8085 0.0107 0.1449 0.046 Uiso 1 1 calc R . . . .
C12 C 0.4886(7) 0.07969(13) 0.81955(11) 0.0514(7) Uani 1 1 d . . . . .
H12A H 0.4036 0.0974 0.7837 0.077 Uiso 1 1 calc GR . . . .
H12B H 0.4650 0.0332 0.8200 0.077 Uiso 1 1 calc GR . . . .
H12C H 0.6819 0.0899 0.8194 0.077 Uiso 1 1 calc GR . . . .
C13 C 0.4679(10) 0.07656(15) 0.93283(13) 0.0666(10) Uani 1 1 d . . . . .
H13A H 0.6563 0.0896 0.9387 0.100 Uiso 1 1 calc GR . . . .
H13B H 0.4591 0.0301 0.9283 0.100 Uiso 1 1 calc GR . . . .
H13C H 0.3602 0.0895 0.9675 0.100 Uiso 1 1 calc GR . . . .
C11 C 0.3541(6) 0.10899(12) 0.87596(11) 0.0415(6) Uani 1 1 d . . . . .
H11 H 0.1555 0.1002 0.8740 0.050 Uiso 1 1 calc R . . . .
C17 C 0.4981(7) -0.04581(12) 0.17981(12) 0.0489(7) Uani 1 1 d . . . . .
H17A H 0.5797 -0.0469 0.2197 0.073 Uiso 1 1 calc GR . . . .
H17B H 0.5450 -0.0849 0.1582 0.073 Uiso 1 1 calc GR . . . .
H17C H 0.3012 -0.0427 0.1835 0.073 Uiso 1 1 calc GR . . . .
O3 O 0.1610(6) 0.17412(14) 0.06002(10) 0.0647(7) Uani 1 1 d . . . . .
H3 H 0.302(7) 0.0758(13) 0.2793(12) 0.026(6) Uiso 1 1 d . . . . .
H2 H 0.650(7) 0.2310(12) 0.7877(12) 0.025(6) Uiso 1 1 d . . . . .
H4C H 0.788(8) 0.1322(16) 0.1321(14) 0.045(8) Uiso 1 1 d . . . . .
H4D H 0.578(9) 0.1697(19) 0.1621(15) 0.054(9) Uiso 1 1 d . . . . .
H1C H 0.083(11) 0.213(2) 0.9244(17) 0.064(11) Uiso 1 1 d . . . . .
H1D H 0.307(7) 0.2527(18) 0.9366(14) 0.045(8) Uiso 1 1 d . . . . .
H3C H 0.201(9) 0.1790(19) 0.023(2) 0.065(10) Uiso 1 1 d . . . . .
H3D H 0.286(9) 0.1631(18) 0.0769(17) 0.054(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C14 1.226(3) . ?
O1 C9 1.227(3) . ?
N3 C14 1.335(3) . ?
N3 C8 1.459(3) . ?
N3 H3 0.79(3) . ?
N2 C9 1.327(3) . ?
N2 C1 1.460(3) . ?
N2 H2 0.83(4) . ?
C15 H15 0.9800 . ?
C15 C14 1.530(3) . ?
C15 N4 1.460(3) . ?
C15 C16 1.539(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C6 1.527(3) . ?
C7 C8 1.511(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.524(3) . ?
C3 C2 1.529(3) . ?
C9 C10 1.531(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.516(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.515(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.527(3) . ?
C10 H10 0.9800 . ?
C10 N1 1.467(3) . ?
C10 C11 1.539(3) . ?
N4 H4C 0.92(4) . ?
N4 H4D 0.88(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
N1 H1C 0.84(5) . ?
N1 H1D 0.88(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18 C16 1.520(3) . ?
C16 H16 0.9800 . ?
C16 C17 1.518(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 C11 1.522(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 C11 1.518(4) . ?
C11 H11 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
O3 H3C 0.84(4) . ?
O3 H3D 0.74(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 N3 C8 122.7(2) . . ?
C14 N3 H3 119.2(19) . . ?
C8 N3 H3 118.0(19) . . ?
C9 N2 C1 122.7(2) . . ?
C9 N2 H2 121.4(18) . . ?
C1 N2 H2 114.7(18) . . ?
C14 C15 H15 108.1 . . ?
C14 C15 C16 108.97(17) . . ?
N4 C15 H15 108.1 . . ?
N4 C15 C14 112.33(18) . . ?
N4 C15 C16 111.22(18) . . ?
C16 C15 H15 108.1 . . ?
O2 C14 N3 123.2(2) . . ?
O2 C14 C15 120.8(2) . . ?
N3 C14 C15 115.97(19) . . ?
H7A C7 H7B 108.0 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C8 C7 C6 111.4(2) . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C4 C3 C2 112.0(2) . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
O1 C9 N2 123.1(2) . . ?
O1 C9 C10 119.9(2) . . ?
N2 C9 C10 116.98(19) . . ?
C7 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C5 C6 C7 114.5(2) . . ?
C5 C6 H6A 108.6 . . ?
C5 C6 H6B 108.6 . . ?
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
N2 C1 C2 110.89(18) . . ?
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C3 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
C3 C4 C5 114.5(2) . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
C9 C10 H10 108.5 . . ?
C9 C10 C11 108.54(18) . . ?
N1 C10 C9 111.30(19) . . ?
N1 C10 H10 108.5 . . ?
N1 C10 C11 111.49(19) . . ?
C11 C10 H10 108.5 . . ?
C15 N4 H4C 111(2) . . ?
C15 N4 H4D 111(2) . . ?
H4C N4 H4D 105(3) . . ?
C6 C5 C4 113.0(2) . . ?
C6 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C4 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C3 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C1 C2 C3 114.29(19) . . ?
C1 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
N3 C8 C7 113.4(2) . . ?
N3 C8 H8A 108.9 . . ?
N3 C8 H8B 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C10 N1 H1C 109(3) . . ?
C10 N1 H1D 110(2) . . ?
H1C N1 H1D 106(4) . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
C15 C16 H16 108.1 . . ?
C18 C16 C15 111.4(2) . . ?
C18 C16 H16 108.1 . . ?
C17 C16 C15 110.7(2) . . ?
C17 C16 C18 110.2(2) . . ?
C17 C16 H16 108.1 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
C10 C11 H11 108.2 . . ?
C12 C11 C10 111.5(2) . . ?
C12 C11 H11 108.2 . . ?
C13 C11 C10 110.8(2) . . ?
C13 C11 C12 109.9(2) . . ?
C13 C11 H11 108.2 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
H3C O3 H3D 109(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 C9 C10 N1 -50.8(3) . . . . ?
O1 C9 C10 C11 72.3(3) . . . . ?
N2 C9 C10 N1 129.1(2) . . . . ?
N2 C9 C10 C11 -107.8(2) . . . . ?
N2 C1 C2 C3 170.8(2) . . . . ?
C14 N3 C8 C7 129.1(2) . . . . ?
C14 C15 C16 C18 -176.3(2) . . . . ?
C14 C15 C16 C17 60.8(3) . . . . ?
C7 C6 C5 C4 -178.1(2) . . . . ?
C3 C4 C5 C6 178.5(2) . . . . ?
C9 N2 C1 C2 -103.5(2) . . . . ?
C9 C10 C11 C12 54.1(3) . . . . ?
C9 C10 C11 C13 176.8(2) . . . . ?
C6 C7 C8 N3 -178.8(2) . . . . ?
C1 N2 C9 O1 -10.2(4) . . . . ?
C1 N2 C9 C10 169.99(19) . . . . ?
C4 C3 C2 C1 178.1(2) . . . . ?
N4 C15 C14 O2 -59.4(3) . . . . ?
N4 C15 C14 N3 121.1(2) . . . . ?
N4 C15 C16 C18 -51.9(3) . . . . ?
N4 C15 C16 C17 -174.9(2) . . . . ?
C2 C3 C4 C5 176.0(2) . . . . ?
C8 N3 C14 O2 -4.8(4) . . . . ?
C8 N3 C14 C15 174.6(2) . . . . ?
C8 C7 C6 C5 177.7(2) . . . . ?
N1 C10 C11 C12 177.1(2) . . . . ?
N1 C10 C11 C13 -60.2(3) . . . . ?
C16 C15 C14 O2 64.3(3) . . . . ?
C16 C15 C14 N3 -115.1(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_str1715
_database_code_depnum_ccdc_archive 'CCDC 1880518'
loop_
_audit_author_name
_audit_author_address
'Vicente Mart? Centelles'
;Universitat Jaume I
Spain
;
_audit_update_record             
;
2018-11-21 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_EXPT005_str1715             
;
PROBLEM: _exptl_crystal_description is missing
RESPONSE: No description was provided.
;
# Added during the CSD deposition process: Wednesday 21 November 2018 05:31 PM
# end Validation Reply Form

_audit_creation_date             2015-11-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H31 N5 O2, 2(H2 O)'
_chemical_formula_sum            'C14 H35 N5 O4'
_chemical_formula_weight         337.47
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H31 N5 O2'
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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
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                   26.1681(6)
_cell_length_b                   4.81178(18)
_cell_length_c                   16.5261(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.807(3)
_cell_angle_gamma                90
_cell_volume                     2002.20(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6406
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.5460
_cell_measurement_theta_min      3.4500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_correction_T_min  0.282
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.9442
_exptl_crystal_size_mid          0.0931
_exptl_crystal_size_min          0.0382
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16100
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        64.971
_diffrn_reflns_theta_max         64.971
_diffrn_reflns_theta_min         3.511
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4051
_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 -116.00   -5.60   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -57.0000   60.0000 138

#__ type_ start__ end____ width___ exp.time_
  2 omega  -95.00   46.60   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057   19.0000  150.0000 177

#__ type_ start__ end____ width___ exp.time_
  3 omega -116.00   -5.60   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -57.0000  150.0000 138

#__ type_ start__ end____ width___ exp.time_
  4 omega   57.00  129.00   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       37.6057  178.0000  120.0000 90

#__ type_ start__ end____ width___ exp.time_
  5 omega   66.00  178.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   77.0000   30.0000 140

#__ type_ start__ end____ width___ exp.time_
  6 omega  100.00  177.60   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686  111.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
  7 omega   68.00  177.60   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   62.0000  129.3950 137

#__ type_ start__ end____ width___ exp.time_
  8 omega   66.00  178.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   77.0000  120.0000 140

#__ type_ start__ end____ width___ exp.time_
  9 omega   66.00  178.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   77.0000   60.0000 140

#__ type_ start__ end____ width___ exp.time_
 10 omega   24.00   96.80   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686  -45.0000   90.0000 91

#__ type_ start__ end____ width___ exp.time_
 11 omega   69.00  177.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   61.0000   90.0000 135

#__ type_ start__ end____ width___ exp.time_
 12 omega   66.00  178.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   77.0000  150.0000 140

#__ type_ start__ end____ width___ exp.time_
 13 omega   69.00  177.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   61.0000  150.0000 135

#__ type_ start__ end____ width___ exp.time_
 14 omega   69.00  177.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   61.0000   30.0000 135

#__ type_ start__ end____ width___ exp.time_
 15 omega   66.00  178.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   77.0000   90.0000 140

#__ type_ start__ end____ width___ exp.time_
 16 omega   15.00  108.60   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686  -94.0000  120.0000 117

#__ type_ start__ end____ width___ exp.time_
 17 omega   69.00  177.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   61.0000   60.0000 135

#__ type_ start__ end____ width___ exp.time_
 18 omega   69.00  177.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   61.0000  120.0000 135

#__ type_ start__ end____ width___ exp.time_
 19 omega   71.00  177.40   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   45.0000 -180.0000 133

#__ type_ start__ end____ width___ exp.time_
 20 omega   69.00  177.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   61.0000 -180.0000 135

#__ type_ start__ end____ width___ exp.time_
 21 omega   67.00  177.40   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   63.0000   95.7746 138

#__ type_ start__ end____ width___ exp.time_
 22 omega   66.00  178.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   77.0000 -180.0000 140

#__ type_ start__ end____ width___ exp.time_
 23 omega   67.00  177.40   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   72.0000   59.2020 138

#__ type_ start__ end____ width___ exp.time_
 24 omega -116.00   -5.60   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -57.0000 -120.0000 138

#__ type_ start__ end____ width___ exp.time_
 25 omega  -49.00   41.40   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057   37.0000  -60.0000 113

#__ type_ start__ end____ width___ exp.time_
 26 omega -122.00   -2.00   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -77.0000    0.0000 150

#__ type_ start__ end____ width___ exp.time_
 27 omega    5.00  115.40   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       37.6057   57.0000    0.0000 138

#__ type_ start__ end____ width___ exp.time_
 28 omega   57.00  129.00   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       37.6057  178.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
 29 omega   64.00  150.40   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   30.0000  -30.0000 108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0119660000
_diffrn_orient_matrix_UB_12      0.0150585000
_diffrn_orient_matrix_UB_13      -0.0964118000
_diffrn_orient_matrix_UB_21      0.0588718000
_diffrn_orient_matrix_UB_22      -0.0576936000
_diffrn_orient_matrix_UB_23      0.0066355000
_diffrn_orient_matrix_UB_31      -0.0113228000
_diffrn_orient_matrix_UB_32      -0.3150351000
_diffrn_orient_matrix_UB_33      -0.0057811000
_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_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_full    0.880
_reflns_Friedel_fraction_max     0.880
_reflns_number_gt                3030
_reflns_number_total             3249
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 1164 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3249
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0548
_refine_ls_restrained_S_all      1.076
_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)+(0.0976P)²+0.8793P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1514
_refine_ls_wR_factor_ref         0.1564
_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,H) groups
2. Restrained distances
 N4-H4 = N5-H5A = N5-H5B = N2-H2
 0.97 with sigma of 0.02
 H1B-N1 = N1-H1A
 0.95 with sigma of 0.02
 N3-H3
 0.95 with sigma of 0.02
 H1B-H1A
 1.527 with sigma of 0.04
3.a Free rotating group:
 O4(H4C,H4D), O3(H3C,H3D)
3.b Ternary CH refined with riding coordinates:
 C11(H11), C6(H6), C12(H12), C7(H7)
3.c Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C3(H3A,H3B), C1(H1C,H1D), C2(H2A,H2B)
3.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C14(H14A,H14B,H14C), C9(H9A,H9B,H9C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O2 O 0.20616(11) -0.1617(6) 0.60033(16) 0.0443(7) Uani 1 1 d . . . . .
O1 O 0.52489(12) -0.1743(7) 0.8884(3) 0.0654(10) Uani 1 1 d . . . . .
N2 N 0.49675(10) 0.2669(7) 0.89222(17) 0.0325(7) Uani 1 1 d D . . . .
N4 N 0.21885(10) 0.2716(7) 0.65452(17) 0.0337(7) Uani 1 1 d D . . . .
O4 O 0.23830(10) 0.5129(8) 0.9546(2) 0.0565(8) Uani 1 1 d . . . . .
H4C H 0.2049 0.5392 0.9405 0.085 Uiso 1 1 d G . . . .
H4D H 0.2455 0.3645 0.9834 0.085 Uiso 1 1 d G . . . .
C10 C 0.19890(11) 0.0909(8) 0.59289(19) 0.0306(7) Uani 1 1 d . . . . .
O3 O 0.33378(10) 0.6405(7) 0.90920(18) 0.0512(8) Uani 1 1 d . . . . .
H3C H 0.3035 0.6213 0.9182 0.077 Uiso 1 1 d G . . . .
H3D H 0.3397 0.5032 0.8807 0.077 Uiso 1 1 d G . . . .
N3 N 0.34945(9) 0.1744(7) 0.81506(15) 0.0314(6) Uani 1 1 d D . . . .
C5 C 0.53240(12) 0.0779(8) 0.8862(2) 0.0358(8) Uani 1 1 d . . . . .
N1 N 0.62947(12) 0.0628(11) 0.9396(3) 0.0584(12) Uani 1 1 d D . . . .
N5 N 0.18810(14) 0.1182(11) 0.4406(2) 0.0565(10) Uani 1 1 d D . . . .
C11 C 0.16684(12) 0.2125(9) 0.50874(19) 0.0352(8) Uani 1 1 d . . . . .
H11 H 0.1695 0.4155 0.5120 0.042 Uiso 1 1 calc R . . . .
C6 C 0.58524(12) 0.1866(9) 0.8771(2) 0.0365(8) Uani 1 1 d . . . . .
H6 H 0.5863 0.3880 0.8861 0.044 Uiso 1 1 calc R . . . .
C4 C 0.25458(11) 0.1900(9) 0.73556(19) 0.0354(8) Uani 1 1 d . . . . .
H4A H 0.2467 0.0011 0.7488 0.042 Uiso 1 1 calc R . . . .
H4B H 0.2492 0.3113 0.7794 0.042 Uiso 1 1 calc R . . . .
C3 C 0.31179(11) 0.2085(9) 0.73226(19) 0.0363(8) Uani 1 1 d . . . . .
H3A H 0.3183 0.0659 0.6948 0.044 Uiso 1 1 calc R . . . .
H3B H 0.3176 0.3877 0.7094 0.044 Uiso 1 1 calc R . . . .
C1 C 0.44332(11) 0.1967(9) 0.89637(19) 0.0362(8) Uani 1 1 d . . . . .
H1C H 0.4321 0.3284 0.9326 0.043 Uiso 1 1 calc R . . . .
H1D H 0.4436 0.0130 0.9206 0.043 Uiso 1 1 calc R . . . .
C2 C 0.40439(11) 0.2019(10) 0.81006(19) 0.0380(8) Uani 1 1 d . . . . .
H2A H 0.4082 0.3752 0.7823 0.046 Uiso 1 1 calc R . . . .
H2B H 0.4124 0.0509 0.7766 0.046 Uiso 1 1 calc R . . . .
C12 C 0.10856(13) 0.1316(11) 0.4904(2) 0.0489(10) Uani 1 1 d . . . . .
H12 H 0.1059 -0.0715 0.4888 0.059 Uiso 1 1 calc R . . . .
C7 C 0.58897(14) 0.1303(11) 0.7869(2) 0.0486(10) Uani 1 1 d . . . . .
H7 H 0.5908 -0.0712 0.7795 0.058 Uiso 1 1 calc R . . . .
C8 C 0.54040(17) 0.2395(15) 0.7215(3) 0.0691(17) Uani 1 1 d . . . . .
H8A H 0.5361 0.4338 0.7310 0.104 Uiso 1 1 calc GR . . . .
H8B H 0.5094 0.1401 0.7258 0.104 Uiso 1 1 calc GR . . . .
H8C H 0.5450 0.2135 0.6663 0.104 Uiso 1 1 calc GR . . . .
C14 C 0.08555(17) 0.2392(19) 0.5602(3) 0.083(2) Uani 1 1 d . . . . .
H14A H 0.0842 0.4385 0.5584 0.124 Uiso 1 1 calc GR . . . .
H14B H 0.1077 0.1801 0.6138 0.124 Uiso 1 1 calc GR . . . .
H14C H 0.0504 0.1666 0.5522 0.124 Uiso 1 1 calc GR . . . .
C9 C 0.63924(16) 0.2597(13) 0.7734(3) 0.0599(13) Uani 1 1 d . . . . .
H9A H 0.6698 0.1741 0.8107 0.090 Uiso 1 1 calc GR . . . .
H9B H 0.6396 0.4554 0.7849 0.090 Uiso 1 1 calc GR . . . .
H9C H 0.6399 0.2311 0.7163 0.090 Uiso 1 1 calc GR . . . .
C13 C 0.07655(16) 0.2464(15) 0.4058(3) 0.0695(16) Uani 1 1 d . . . . .
H13A H 0.0907 0.1755 0.3621 0.104 Uiso 1 1 calc GR . . . .
H13B H 0.0786 0.4456 0.4066 0.104 Uiso 1 1 calc GR . . . .
H13C H 0.0401 0.1903 0.3953 0.104 Uiso 1 1 calc GR . . . .
H5A H 0.2216(15) 0.203(14) 0.446(4) 0.080(18) Uiso 1 1 d D . . . .
H4 H 0.213(2) 0.467(6) 0.645(4) 0.08(2) Uiso 1 1 d D . . . .
H2 H 0.507(2) 0.457(7) 0.887(3) 0.071(16) Uiso 1 1 d D . . . .
H5B H 0.191(3) -0.082(6) 0.445(4) 0.09(2) Uiso 1 1 d D . . . .
H1A H 0.623(3) -0.130(7) 0.931(4) 0.09(2) Uiso 1 1 d D . . . .
H1B H 0.638(3) 0.098(18) 0.998(2) 0.13(3) Uiso 1 1 d D . . . .
H3 H 0.3448(17) -0.007(6) 0.837(3) 0.042(11) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C10 1.231(5) . ?
O1 C5 1.231(5) . ?
N2 C5 1.326(5) . ?
N2 C1 1.458(4) . ?
N2 H2 0.96(3) . ?
N4 C10 1.333(5) . ?
N4 C4 1.463(4) . ?
N4 H4 0.96(3) . ?
O4 H4C 0.8510 . ?
O4 H4D 0.8500 . ?
C10 C11 1.531(4) . ?
O3 H3C 0.8495 . ?
O3 H3D 0.8501 . ?
N3 C3 1.461(4) . ?
N3 C2 1.468(4) . ?
N3 H3 0.96(3) . ?
C5 C6 1.524(4) . ?
N1 C6 1.453(5) . ?
N1 H1A 0.95(3) . ?
N1 H1B 0.95(3) . ?
N5 C11 1.457(5) . ?
N5 H5A 0.95(3) . ?
N5 H5B 0.97(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.522(4) . ?
C6 H6 0.9800 . ?
C6 C7 1.543(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.516(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C1 C2 1.510(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C12 H12 0.9800 . ?
C12 C14 1.529(7) . ?
C12 C13 1.525(6) . ?
C7 H7 0.9800 . ?
C7 C8 1.521(6) . ?
C7 C9 1.525(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N2 C1 123.2(3) . . ?
C5 N2 H2 115(4) . . ?
C1 N2 H2 121(4) . . ?
C10 N4 C4 123.0(3) . . ?
C10 N4 H4 120(4) . . ?
C4 N4 H4 116(4) . . ?
H4C O4 H4D 109.4 . . ?
O2 C10 N4 123.4(3) . . ?
O2 C10 C11 120.0(3) . . ?
N4 C10 C11 116.6(3) . . ?
H3C O3 H3D 109.5 . . ?
C3 N3 C2 111.0(2) . . ?
C3 N3 H3 109(3) . . ?
C2 N3 H3 109(3) . . ?
O1 C5 N2 123.5(3) . . ?
O1 C5 C6 119.8(3) . . ?
N2 C5 C6 116.6(3) . . ?
C6 N1 H1A 102(4) . . ?
C6 N1 H1B 125(5) . . ?
H1A N1 H1B 108(5) . . ?
C11 N5 H5A 109(4) . . ?
C11 N5 H5B 108(4) . . ?
H5A N5 H5B 111(6) . . ?
C10 C11 H11 108.5 . . ?
N5 C11 C10 110.6(3) . . ?
N5 C11 H11 108.5 . . ?
N5 C11 C12 109.8(3) . . ?
C12 C11 C10 110.8(3) . . ?
C12 C11 H11 108.5 . . ?
C5 C6 H6 108.3 . . ?
C5 C6 C7 109.5(3) . . ?
N1 C6 C5 110.9(3) . . ?
N1 C6 H6 108.3 . . ?
N1 C6 C7 111.5(3) . . ?
C7 C6 H6 108.3 . . ?
N4 C4 H4A 109.7 . . ?
N4 C4 H4B 109.7 . . ?
N4 C4 C3 110.0(3) . . ?
H4A C4 H4B 108.2 . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
N3 C3 C4 112.4(2) . . ?
N3 C3 H3A 109.1 . . ?
N3 C3 H3B 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
N2 C1 H1C 109.4 . . ?
N2 C1 H1D 109.4 . . ?
N2 C1 C2 111.1(3) . . ?
H1C C1 H1D 108.0 . . ?
C2 C1 H1C 109.4 . . ?
C2 C1 H1D 109.4 . . ?
N3 C2 C1 111.4(2) . . ?
N3 C2 H2A 109.4 . . ?
N3 C2 H2B 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C11 C12 H12 108.6 . . ?
C11 C12 C14 110.0(4) . . ?
C11 C12 C13 111.1(3) . . ?
C14 C12 H12 108.6 . . ?
C13 C12 H12 108.6 . . ?
C13 C12 C14 109.8(4) . . ?
C6 C7 H7 108.2 . . ?
C8 C7 C6 111.4(3) . . ?
C8 C7 H7 108.2 . . ?
C8 C7 C9 110.0(4) . . ?
C9 C7 C6 110.7(3) . . ?
C9 C7 H7 108.2 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
O2 C10 C11 N5 -53.1(4) . . . . ?
O2 C10 C11 C12 69.0(4) . . . . ?
O1 C5 C6 N1 -51.9(5) . . . . ?
O1 C5 C6 C7 71.6(5) . . . . ?
N2 C5 C6 N1 127.5(4) . . . . ?
N2 C5 C6 C7 -109.0(4) . . . . ?
N2 C1 C2 N3 -171.2(3) . . . . ?
N4 C10 C11 N5 125.2(4) . . . . ?
N4 C10 C11 C12 -112.7(4) . . . . ?
N4 C4 C3 N3 170.5(3) . . . . ?
C10 N4 C4 C3 90.7(4) . . . . ?
C10 C11 C12 C14 59.5(5) . . . . ?
C10 C11 C12 C13 -178.7(4) . . . . ?
C5 N2 C1 C2 -93.7(4) . . . . ?
C5 C6 C7 C8 52.2(5) . . . . ?
C5 C6 C7 C9 174.9(4) . . . . ?
N1 C6 C7 C8 175.4(4) . . . . ?
N1 C6 C7 C9 -61.9(5) . . . . ?
N5 C11 C12 C14 -178.0(4) . . . . ?
N5 C11 C12 C13 -56.2(5) . . . . ?
C4 N4 C10 O2 4.5(5) . . . . ?
C4 N4 C10 C11 -173.8(3) . . . . ?
C3 N3 C2 C1 174.1(3) . . . . ?
C1 N2 C5 O1 -4.3(6) . . . . ?
C1 N2 C5 C6 176.3(3) . . . . ?
C2 N3 C3 C4 -178.3(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1 0 -10 0.0182 0.9995 0.0060 -10.0011 0.9524 -0.0079 0.0446
3 3 -1 0.4620 2.9927 3.0019 -0.9988 0.1057 -0.0036 -0.9738
-1 0 10 0.0199 -0.9995 -0.0060 10.0011 -0.9524 0.0079 -0.0446
-17 0 2 0.0830 -17.0041 -0.0045 2.0031 0.0103 -0.9875 0.1824
17 0 -2 0.0101 17.0041 0.0045 -2.0031 -0.0103 0.9875 -0.1824
-3 -3 0 0.4551 -2.9927 -3.0013 -0.0013 -0.0093 -0.0030 0.9794
3 3 0 0.4551 2.9927 3.0013 0.0013 0.0093 0.0030 -0.9794
8 0 8 0.0100 8.0026 -0.0031 7.9993 -0.8670 0.5244 -0.1359
-8 0 -8 0.0449 -8.0026 0.0031 -7.9993 0.8670 -0.5244 0.1359

_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_str1750
_database_code_depnum_ccdc_archive 'CCDC 1880521'
loop_
_audit_author_name
_audit_author_address
'Vicente Mart? Centelles'
;Universitat Jaume I
Spain
;
_audit_update_record             
;
2018-11-21 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_EXPT005_str1750             
;
PROBLEM: _exptl_crystal_description is missing
RESPONSE: No description was provided.
;
# Added during the CSD deposition process: Wednesday 21 November 2018 05:31 PM
# end Validation Reply Form

_audit_creation_date             2015-11-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H32 N4 O2'
_chemical_formula_sum            'C23 H32 N4 O2'
_chemical_formula_weight         396.52
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H32 N4 O2'
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                   25.6360(3)
_cell_length_b                   16.5436(2)
_cell_length_c                   5.05085(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2142.12(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.3050
_cell_measurement_theta_min      3.3990
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.3512
_exptl_crystal_size_mid          0.0585
_exptl_crystal_size_min          0.0346
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            19750
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.500
_diffrn_reflns_theta_min         3.448
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4051
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -74.00   38.20   0.6000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680   77.0000  -30.0000 187

#__ type_ start__ end____ width___ exp.time_
  2 omega  -50.00   35.20   0.6000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680   38.0000 -150.0000 142

#__ type_ start__ end____ width___ exp.time_
  3 omega   55.00  127.00   0.6000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       40.0680 -178.0000 -150.0000 120

#__ type_ start__ end____ width___ exp.time_
  4 omega   28.00   88.60   0.6000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -30.0000    0.0000 101

#__ type_ start__ end____ width___ exp.time_
  5 omega   28.00   88.60   0.6000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -30.0000 -120.0000 101

#__ type_ start__ end____ width___ exp.time_
  6 omega  100.00  178.00   0.6000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  110.0000  170.0000 130

#__ type_ start__ end____ width___ exp.time_
  7 omega   28.00   88.60   0.6000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -30.0000  120.0000 101

#__ type_ start__ end____ width___ exp.time_
  8 omega   28.00   88.60   0.6000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -30.0000   60.0000 101

#__ type_ start__ end____ width___ exp.time_
  9 omega   31.00   97.00   0.6000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -45.0000  -60.0000 110

#__ type_ start__ end____ width___ exp.time_
 10 omega   16.00  178.00   0.6000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400    0.0000  -90.0000 270

#__ type_ start__ end____ width___ exp.time_
 11 omega -114.00  -10.80   0.6000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -57.0000  -30.0000 172

#__ type_ start__ end____ width___ exp.time_
 12 omega -119.00   -6.80   0.6000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -77.0000   90.0000 187

#__ type_ start__ end____ width___ exp.time_
 13 omega -114.00  -10.80   0.6000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -57.0000 -120.0000 172

#__ type_ start__ end____ width___ exp.time_
 14 omega   21.00  108.00   0.6000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -94.0000  120.0000 145

#__ type_ start__ end____ width___ exp.time_
 15 omega   44.00  177.20   0.6000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400   15.0000   90.0000 222

#__ type_ start__ end____ width___ exp.time_
 16 omega   78.00  173.40   0.6000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400   45.0000  -30.0000 159

#__ type_ start__ end____ width___ exp.time_
 17 omega   94.00  178.00   0.6000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  125.0000   30.0000 140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0310902000
_diffrn_orient_matrix_UB_12      0.0719818000
_diffrn_orient_matrix_UB_13      0.1120155000
_diffrn_orient_matrix_UB_21      -0.0496848000
_diffrn_orient_matrix_UB_22      0.0317995000
_diffrn_orient_matrix_UB_23      0.1363066000
_diffrn_orient_matrix_UB_31      0.0132318000
_diffrn_orient_matrix_UB_32      -0.0497833000
_diffrn_orient_matrix_UB_33      0.2488721000
_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_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                4027
_reflns_number_total             4201
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1601 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4201
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.036
_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)+(0.0758P)²+0.1340P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1059
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N4-H4B = N4-H4A = N3-H3 = N2-H2 = N1-H1A = N1-H1B
 0.97 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C16(H16), C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C1(H1C,H1D), C5(H5A,H5B), C2(H2A,H2B), C8(H8A,H8B), C4(H4C,H4D),
 C17(H17A,H17B)
3.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C10(H10), C12(H12), C14(H14), C11(H11), C23(H23), C22(H22),
 C20(H20), C19(H19), C21(H21)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O2 O 0.63689(5) 0.34707(10) 0.1521(3) 0.0392(3) Uani 1 1 d . . . . .
O1 O 0.90411(6) 0.21724(10) 1.3138(3) 0.0431(3) Uani 1 1 d . . . . .
N2 N 0.90013(5) 0.24693(9) 0.8785(3) 0.0301(3) Uani 1 1 d D . . . .
N3 N 0.65982(5) 0.34230(10) 0.5823(3) 0.0309(3) Uani 1 1 d D . . . .
N4 N 0.54358(7) 0.42651(11) 0.3964(5) 0.0461(4) Uani 1 1 d D . . . .
N1 N 0.95225(6) 0.06737(11) 1.1099(5) 0.0456(4) Uani 1 1 d D . . . .
C13 C 0.73695(9) 0.06236(14) 0.6994(5) 0.0460(5) Uani 1 1 d . . . . .
H13 H 0.7241 0.0337 0.5551 0.055 Uiso 1 1 calc R . . . .
C3 C 0.80634(7) 0.34675(13) 0.7109(4) 0.0348(4) Uani 1 1 d . . . . .
H3A H 0.8096 0.2904 0.6602 0.042 Uiso 1 1 calc R . . . .
H3B H 0.8191 0.3794 0.5650 0.042 Uiso 1 1 calc R . . . .
C16 C 0.56738(6) 0.34942(12) 0.4697(4) 0.0329(4) Uani 1 1 d . . . . .
H16 H 0.5649 0.3427 0.6621 0.040 Uiso 1 1 calc R . . . .
C6 C 0.90249(6) 0.19516(11) 1.0800(4) 0.0301(4) Uani 1 1 d . . . . .
C1 C 0.89657(7) 0.33401(12) 0.9157(4) 0.0361(4) Uani 1 1 d . . . . .
H1C H 0.9115 0.3610 0.7631 0.043 Uiso 1 1 calc R . . . .
H1D H 0.9168 0.3493 1.0701 0.043 Uiso 1 1 calc R . . . .
C10 C 0.77583(7) 0.14766(13) 1.1250(4) 0.0406(4) Uani 1 1 d . . . . .
H10 H 0.7887 0.1771 1.2676 0.049 Uiso 1 1 calc R . . . .
C12 C 0.70783(8) 0.12390(14) 0.8091(5) 0.0430(5) Uani 1 1 d . . . . .
H12 H 0.6751 0.1363 0.7407 0.052 Uiso 1 1 calc R . . . .
C5 C 0.71566(6) 0.33447(12) 0.5302(4) 0.0321(4) Uani 1 1 d . . . . .
H5A H 0.7242 0.3640 0.3702 0.039 Uiso 1 1 calc R . . . .
H5B H 0.7239 0.2780 0.5002 0.039 Uiso 1 1 calc R . . . .
C14 C 0.78543(8) 0.04316(12) 0.8039(5) 0.0403(4) Uani 1 1 d . . . . .
H14 H 0.8048 0.0016 0.7284 0.048 Uiso 1 1 calc R . . . .
C11 C 0.72733(8) 0.16673(13) 1.0198(5) 0.0443(5) Uani 1 1 d . . . . .
H11 H 0.7079 0.2088 1.0924 0.053 Uiso 1 1 calc R . . . .
C2 C 0.84015(7) 0.36214(11) 0.9520(4) 0.0345(4) Uani 1 1 d . . . . .
H2A H 0.8251 0.3343 1.1029 0.041 Uiso 1 1 calc R . . . .
H2B H 0.8400 0.4196 0.9907 0.041 Uiso 1 1 calc R . . . .
C23 C 0.52950(11) 0.16023(17) 0.6310(6) 0.0591(6) Uani 1 1 d . . . . .
H23 H 0.5042 0.1875 0.7277 0.071 Uiso 1 1 calc R . . . .
C8 C 0.85748(8) 0.06156(13) 1.1347(4) 0.0408(5) Uani 1 1 d . . . . .
H8A H 0.8623 0.0038 1.1120 0.049 Uiso 1 1 calc R . . . .
H8B H 0.8569 0.0725 1.3234 0.049 Uiso 1 1 calc R . . . .
C9 C 0.80546(7) 0.08492(11) 1.0195(4) 0.0341(4) Uani 1 1 d . . . . .
C4 C 0.74876(7) 0.36593(12) 0.7556(4) 0.0327(4) Uani 1 1 d . . . . .
H4C H 0.7373 0.3415 0.9203 0.039 Uiso 1 1 calc R . . . .
H4D H 0.7443 0.4240 0.7706 0.039 Uiso 1 1 calc R . . . .
C17 C 0.53663(7) 0.28129(12) 0.3346(5) 0.0399(4) Uani 1 1 d . . . . .
H17A H 0.4999 0.2881 0.3751 0.048 Uiso 1 1 calc R . . . .
H17B H 0.5407 0.2866 0.1444 0.048 Uiso 1 1 calc R . . . .
C15 C 0.62477(6) 0.34564(11) 0.3883(4) 0.0283(3) Uani 1 1 d . . . . .
C7 C 0.90447(7) 0.10552(11) 1.0120(4) 0.0336(4) Uani 1 1 d . . . . .
H7 H 0.9030 0.0994 0.8192 0.040 Uiso 1 1 calc R . . . .
C18 C 0.55281(7) 0.19734(12) 0.4139(5) 0.0397(4) Uani 1 1 d . . . . .
C22 C 0.54399(15) 0.0827(2) 0.7030(7) 0.0788(10) Uani 1 1 d . . . . .
H22 H 0.5285 0.0585 0.8495 0.095 Uiso 1 1 calc R . . . .
C20 C 0.60446(12) 0.07735(17) 0.3491(7) 0.0665(8) Uani 1 1 d . . . . .
H20 H 0.6299 0.0498 0.2537 0.080 Uiso 1 1 calc R . . . .
C19 C 0.59063(9) 0.15509(14) 0.2760(5) 0.0488(5) Uani 1 1 d . . . . .
H19 H 0.6070 0.1793 0.1321 0.059 Uiso 1 1 calc R . . . .
C21 C 0.58102(15) 0.04089(17) 0.5604(8) 0.0790(11) Uani 1 1 d . . . . .
H21 H 0.5900 -0.0117 0.6076 0.095 Uiso 1 1 calc R . . . .
H2 H 0.8987(9) 0.2268(14) 0.714(4) 0.034(6) Uiso 1 1 d D . . . .
H3 H 0.6490(10) 0.3393(15) 0.750(4) 0.037(6) Uiso 1 1 d D . . . .
H4A H 0.5582(14) 0.441(2) 0.230(6) 0.079(11) Uiso 1 1 d D . . . .
H1A H 0.9806(10) 0.0805(19) 0.996(6) 0.065(9) Uiso 1 1 d D . . . .
H1B H 0.9609(12) 0.0914(18) 1.275(5) 0.060(9) Uiso 1 1 d D . . . .
H4B H 0.5515(12) 0.4655(16) 0.523(5) 0.057(8) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C15 1.233(2) . ?
O1 C6 1.237(2) . ?
N2 C6 1.332(3) . ?
N2 C1 1.456(2) . ?
N2 H2 0.896(19) . ?
N3 C5 1.461(2) . ?
N3 C15 1.330(2) . ?
N3 H3 0.89(2) . ?
N4 C16 1.462(3) . ?
N4 H4A 0.95(2) . ?
N4 H4B 0.93(2) . ?
N1 C7 1.464(2) . ?
N1 H1A 0.95(2) . ?
N1 H1B 0.95(2) . ?
C13 H13 0.9300 . ?
C13 C12 1.379(3) . ?
C13 C14 1.387(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.516(3) . ?
C3 C4 1.526(2) . ?
C16 H16 0.9800 . ?
C16 C17 1.535(3) . ?
C16 C15 1.529(2) . ?
C6 C7 1.523(3) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C1 C2 1.530(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.389(3) . ?
C10 C9 1.392(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.373(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.512(2) . ?
C14 H14 0.9300 . ?
C14 C9 1.388(3) . ?
C11 H11 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C23 H23 0.9300 . ?
C23 C18 1.392(3) . ?
C23 C22 1.384(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.506(3) . ?
C8 C7 1.537(3) . ?
C4 H4C 0.9700 . ?
C4 H4D 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.504(3) . ?
C7 H7 0.9800 . ?
C18 C19 1.383(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.378(6) . ?
C20 H20 0.9300 . ?
C20 C19 1.384(4) . ?
C20 C21 1.365(5) . ?
C19 H19 0.9300 . ?
C21 H21 0.9300 . ?

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
C6 N2 C1 122.73(16) . . ?
C6 N2 H2 118.2(15) . . ?
C1 N2 H2 119.0(15) . . ?
C5 N3 H3 118.0(16) . . ?
C15 N3 C5 122.20(15) . . ?
C15 N3 H3 119.4(16) . . ?
C16 N4 H4A 107(2) . . ?
C16 N4 H4B 109.8(19) . . ?
H4A N4 H4B 110(3) . . ?
C7 N1 H1A 110(2) . . ?
C7 N1 H1B 108.2(19) . . ?
H1A N1 H1B 105(3) . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.1(2) . . ?
C14 C13 H13 120.0 . . ?
H3A C3 H3B 107.7 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C2 C3 C4 113.51(16) . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
N4 C16 H16 108.9 . . ?
N4 C16 C17 108.28(16) . . ?
N4 C16 C15 111.66(16) . . ?
C17 C16 H16 108.9 . . ?
C15 C16 H16 108.9 . . ?
C15 C16 C17 110.15(15) . . ?
O1 C6 N2 122.78(18) . . ?
O1 C6 C7 120.10(17) . . ?
N2 C6 C7 117.10(16) . . ?
N2 C1 H1C 109.2 . . ?
N2 C1 H1D 109.2 . . ?
N2 C1 C2 112.07(15) . . ?
H1C C1 H1D 107.9 . . ?
C2 C1 H1C 109.2 . . ?
C2 C1 H1D 109.2 . . ?
C11 C10 H10 119.6 . . ?
C11 C10 C9 120.8(2) . . ?
C9 C10 H10 119.6 . . ?
C13 C12 H12 120.1 . . ?
C11 C12 C13 119.7(2) . . ?
C11 C12 H12 120.1 . . ?
N3 C5 H5A 109.1 . . ?
N3 C5 H5B 109.1 . . ?
N3 C5 C4 112.58(15) . . ?
H5A C5 H5B 107.8 . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C13 C14 H14 119.5 . . ?
C13 C14 C9 121.06(19) . . ?
C9 C14 H14 119.5 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C3 C2 C1 113.14(16) . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C18 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C18 120.1(3) . . ?
H8A C8 H8B 107.6 . . ?
C9 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
C9 C8 C7 114.63(16) . . ?
C7 C8 H8A 108.6 . . ?
C7 C8 H8B 108.6 . . ?
C10 C9 C8 121.77(19) . . ?
C14 C9 C10 118.02(19) . . ?
C14 C9 C8 120.21(18) . . ?
C3 C4 H4C 109.4 . . ?
C3 C4 H4D 109.4 . . ?
C5 C4 C3 111.08(15) . . ?
C5 C4 H4C 109.4 . . ?
C5 C4 H4D 109.4 . . ?
H4C C4 H4D 108.0 . . ?
C16 C17 H17A 108.6 . . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C18 C17 C16 114.70(16) . . ?
C18 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
O2 C15 N3 122.89(16) . . ?
O2 C15 C16 120.12(16) . . ?
N3 C15 C16 116.98(15) . . ?
N1 C7 C6 111.81(16) . . ?
N1 C7 C8 108.39(16) . . ?
N1 C7 H7 108.8 . . ?
C6 C7 C8 110.10(16) . . ?
C6 C7 H7 108.8 . . ?
C8 C7 H7 108.8 . . ?
C23 C18 C17 119.9(2) . . ?
C19 C18 C23 118.3(2) . . ?
C19 C18 C17 121.7(2) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 C23 120.9(3) . . ?
C21 C22 H22 119.6 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C21 C20 C19 120.4(3) . . ?
C18 C19 C20 121.0(3) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C22 C21 H21 120.3 . . ?
C20 C21 C22 119.3(3) . . ?
C20 C21 H21 120.3 . . ?

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 C6 C7 N1 -59.3(2) . . . . ?
O1 C6 C7 C8 61.2(2) . . . . ?
N2 C6 C7 N1 119.28(19) . . . . ?
N2 C6 C7 C8 -120.17(18) . . . . ?
N2 C1 C2 C3 -63.4(2) . . . . ?
N3 C5 C4 C3 172.50(16) . . . . ?
N4 C16 C17 C18 -173.75(18) . . . . ?
N4 C16 C15 O2 -64.8(2) . . . . ?
N4 C16 C15 N3 114.0(2) . . . . ?
C13 C12 C11 C10 -0.9(4) . . . . ?
C13 C14 C9 C10 -1.1(3) . . . . ?
C13 C14 C9 C8 178.3(2) . . . . ?
C16 C17 C18 C23 88.9(2) . . . . ?
C16 C17 C18 C19 -91.1(2) . . . . ?
C6 N2 C1 C2 -85.9(2) . . . . ?
C1 N2 C6 O1 -3.2(3) . . . . ?
C1 N2 C6 C7 178.21(15) . . . . ?
C12 C13 C14 C9 0.1(4) . . . . ?
C5 N3 C15 O2 -4.3(3) . . . . ?
C5 N3 C15 C16 176.91(16) . . . . ?
C14 C13 C12 C11 0.9(4) . . . . ?
C11 C10 C9 C14 1.1(3) . . . . ?
C11 C10 C9 C8 -178.3(2) . . . . ?
C2 C3 C4 C5 -168.92(16) . . . . ?
C23 C18 C19 C20 1.0(3) . . . . ?
C23 C22 C21 C20 1.5(5) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C9 C8 C7 N1 -170.56(19) . . . . ?
C9 C8 C7 C6 66.9(2) . . . . ?
C4 C3 C2 C1 173.61(17) . . . . ?
C17 C16 C15 O2 55.5(2) . . . . ?
C17 C16 C15 N3 -125.62(18) . . . . ?
C17 C18 C19 C20 -178.9(2) . . . . ?
C15 N3 C5 C4 156.10(17) . . . . ?
C15 C16 C17 C18 63.9(2) . . . . ?
C7 C8 C9 C10 -90.7(2) . . . . ?
C7 C8 C9 C14 90.0(2) . . . . ?
C18 C23 C22 C21 -0.7(5) . . . . ?
C22 C23 C18 C17 179.4(2) . . . . ?
C22 C23 C18 C19 -0.5(4) . . . . ?
C19 C20 C21 C22 -1.0(5) . . . . ?
C21 C20 C19 C18 -0.2(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
16 -2 0 0.0173 16.0018 -1.9439 -0.0061 0.3569 -0.8577 0.3070
-16 2 0 0.0173 -16.0018 1.9439 0.0061 -0.3569 0.8577 -0.3070
0 -6 3 0.1227 0.0526 -6.0014 3.0024 -0.0940 0.2158 1.0467
3 5 -3 0.1680 2.9514 5.0118 -3.0032 0.1161 -0.3966 -0.9579
1 11 0 0.0268 0.9354 11.0060 -0.0056 0.8207 0.3027 -0.5369
-1 -11 0 0.0268 -0.9354 -11.0060 0.0056 -0.8207 -0.3027 0.5369
3 8 2 0.0834 2.9634 8.0123 1.9947 0.8923 0.3794 0.1368
-10 8 0 0.0216 -10.0404 7.9664 0.0007 0.2614 0.7523 -0.5293

_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_str1717_sq
_database_code_depnum_ccdc_archive 'CCDC 1880519'
loop_
_audit_author_name
_audit_author_address
'Vicente Mart? Centelles'
;Universitat Jaume I
Spain
;
_audit_update_record             
;
2018-11-21 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_EXPT005_str1717_sq          
;
PROBLEM: _exptl_crystal_description is missing
RESPONSE: No description was provided.
;
_vrf_PLAT094_str1717_sq          
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       4.12 Report
RESPONSE: See SQUEEZE section in the CIF file.
;
_vrf_PLAT097_str1717_sq          
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.27 eA-3
RESPONSE: See SQUEEZE section in the CIF file.
;
# Added during the CSD deposition process: Wednesday 21 November 2018 05:31 PM
# end Validation Reply Form

_audit_creation_date             2017-10-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H31.7 N4 O2'
_chemical_formula_sum            'C15 H31.56 N4 O2'
_chemical_formula_weight         300.00
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H32 N4 O2'
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           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   20.4259(4)
_cell_length_b                   4.79492(9)
_cell_length_c                   21.6606(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.636(2)
_cell_angle_gamma                90
_cell_volume                     2070.08(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5626
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.7810
_cell_measurement_theta_min      4.1460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.516
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    0.963
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             662
_exptl_crystal_size_max          0.7711
_exptl_crystal_size_mid          0.0913
_exptl_crystal_size_min          0.0542
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9488
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        65.989
_diffrn_reflns_theta_max         65.989
_diffrn_reflns_theta_min         3.364
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4051
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -122.00   20.40   0.8000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -19.0000 -180.0000 178

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   42.20   0.8000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057   37.0000 -180.0000 114

#__ type_ start__ end____ width___ exp.time_
  3 omega   20.00  109.60   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -94.0000 -150.0000 112

#__ type_ start__ end____ width___ exp.time_
  4 omega   26.00   90.80   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -30.0000 -180.0000 81

#__ type_ start__ end____ width___ exp.time_
  5 omega   28.00   98.40   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -45.0000  -30.0000 88

#__ type_ start__ end____ width___ exp.time_
  6 omega  100.00  178.40   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  111.0000 -150.0000 98

#__ type_ start__ end____ width___ exp.time_
  7 omega   76.00  178.40   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   45.0000  -60.0000 128

#__ type_ start__ end____ width___ exp.time_
  8 omega   69.00  178.60   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   30.0000    0.0000 137

#__ type_ start__ end____ width___ exp.time_
  9 omega  100.00  178.40   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  111.0000 -120.0000 98

#__ type_ start__ end____ width___ exp.time_
 10 omega -116.00   -4.80   0.8000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -57.0000   60.0000 139

#__ type_ start__ end____ width___ exp.time_
 11 omega -122.00   -2.00   0.8000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -77.0000  150.0000 150

#__ type_ start__ end____ width___ exp.time_
 12 omega   20.00  109.60   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -94.0000  -30.0000 112

#__ type_ start__ end____ width___ exp.time_
 13 omega   69.00  178.60   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   30.0000 -150.0000 137

#__ type_ start__ end____ width___ exp.time_
 14 omega   74.00  178.00   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   61.0000   60.0000 130

#__ type_ start__ end____ width___ exp.time_
 15 omega   74.00  178.00   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   61.0000    0.0000 130

#__ type_ start__ end____ width___ exp.time_
 16 omega   74.00  178.00   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   61.0000 -120.0000 130

#__ type_ start__ end____ width___ exp.time_
 17 omega   76.00  178.40   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   45.0000  120.0000 128

#__ type_ start__ end____ width___ exp.time_
 18 omega    2.00  122.00   0.8000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.6057   77.0000    0.0000 150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0477741000
_diffrn_orient_matrix_UB_12      -0.0722223000
_diffrn_orient_matrix_UB_13      0.0634207000
_diffrn_orient_matrix_UB_21      -0.0577376000
_diffrn_orient_matrix_UB_22      -0.1499630000
_diffrn_orient_matrix_UB_23      0.0217596000
_diffrn_orient_matrix_UB_31      0.0189509000
_diffrn_orient_matrix_UB_32      -0.2748719000
_diffrn_orient_matrix_UB_33      -0.0285449000
_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_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_full    0.871
_reflns_Friedel_fraction_max     0.871
_reflns_number_gt                3237
_reflns_number_total             3413
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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         1.266
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.149
_refine_ls_abs_structure_details 
;
 Flack x determined using 1202 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3413
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0613
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1118P)²+0.6552P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1717
_refine_ls_wR_factor_ref         0.1775
_refine_special_details          SQUEEZE
_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
 N3-H3
 0.95 with sigma of 0.02
 N2-H2
 0.95 with sigma of 0.02
 H1C-N1 = N1-H1D
 0.95 with sigma of 0.02
 H4AA-N4A = N4A-H4AB
 0.95 with sigma of 0.01
 H1C-H1D
 1.527 with sigma of 0.04
 H4AA-H4AB
 1.527 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(N4A) \\sim Ueq, Uanis(N4B) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(N4A) \\sim Ueq, Uanis(N4B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
4. Others
 Sof(H12A)=Sof(N4B)=1-FVAR(1)
 Sof(H12)=Sof(N4A)=Sof(H4AA)=Sof(H4AB)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C12(H12), C12(H12A), C13(H13), C8(H8), C7(H7)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1(H1A,H1B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
5.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
C6 C -0.32986(16) -0.3428(7) -0.21075(15) 0.0491(7) Uani 1 1 d . . . . .
C11 C -0.77248(16) -0.3610(7) -0.35939(13) 0.0489(7) Uani 1 1 d . . . . .
N2 N -0.36743(13) -0.5288(6) -0.24736(12) 0.0504(6) Uani 1 1 d D . . . .
N3 N -0.73143(13) -0.5414(6) -0.37809(12) 0.0491(6) Uani 1 1 d D . . . .
O2 O -0.76263(14) -0.1101(5) -0.35497(14) 0.0683(7) Uani 1 1 d . . . . .
C2 C -0.48711(18) -0.4946(11) -0.28971(17) 0.0674(10) Uani 1 1 d . . . . .
H2A H -0.4924 -0.3693 -0.2560 0.081 Uiso 1 1 calc R . . . .
H2B H -0.4913 -0.6838 -0.2752 0.081 Uiso 1 1 calc R . . . .
O1 O -0.33300(18) -0.0929(6) -0.22199(14) 0.0775(8) Uani 1 1 d . . . . .
C1 C -0.41938(17) -0.4578(9) -0.30164(17) 0.0631(9) Uani 1 1 d . . . . .
H1A H -0.4148 -0.5742 -0.3371 0.076 Uiso 1 1 calc R . . . .
H1B H -0.4138 -0.2652 -0.3132 0.076 Uiso 1 1 calc R . . . .
C3 C -0.54346(16) -0.4399(9) -0.34734(16) 0.0628(9) Uani 1 1 d . . . . .
H3A H -0.5416 -0.2466 -0.3600 0.075 Uiso 1 1 calc R . . . .
H3B H -0.5367 -0.5559 -0.3821 0.075 Uiso 1 1 calc R . . . .
C12 C -0.83419(16) -0.4847(7) -0.34060(15) 0.0528(7) Uani 1 1 d . . . . .
H12 H -0.8332 -0.6883 -0.3440 0.063 Uiso 0.85(2) 1 calc R . P A 1
H12A H -0.8336 -0.6662 -0.3613 0.063 Uiso 0.15(2) 1 calc R . P A 2
C4 C -0.61116(16) -0.4988(10) -0.33471(17) 0.0631(9) Uani 1 1 d . . . . .
H4A H -0.6186 -0.3763 -0.3013 0.076 Uiso 1 1 calc R . . . .
H4B H -0.6120 -0.6893 -0.3198 0.076 Uiso 1 1 calc R . . . .
C5 C -0.66802(15) -0.4597(9) -0.39244(16) 0.0601(9) Uani 1 1 d . . . . .
H5A H -0.6702 -0.2657 -0.4054 0.072 Uiso 1 1 calc R . . . .
H5B H -0.6596 -0.5719 -0.4271 0.072 Uiso 1 1 calc R . . . .
C13 C -0.89785(19) -0.3739(11) -0.3828(2) 0.0751(11) Uani 1 1 d . . . . .
H13 H -0.8992 -0.1706 -0.3786 0.090 Uiso 1 1 calc R . . . .
C15 C -0.9605(2) -0.5009(15) -0.3654(3) 0.0943(15) Uani 1 1 d . . . . .
H15A H -0.9589 -0.7004 -0.3687 0.141 Uiso 1 1 calc GR . . . .
H15B H -0.9999 -0.4320 -0.3939 0.141 Uiso 1 1 calc GR . . . .
H15C H -0.9618 -0.4497 -0.3229 0.141 Uiso 1 1 calc GR . . . .
N4A N -0.8360(3) -0.405(3) -0.2744(2) 0.087(3) Uani 0.85(2) 1 d D U P A 1
C14 C -0.8972(3) -0.449(3) -0.4512(2) 0.154(4) Uani 1 1 d . . . . .
H14A H -0.8589 -0.3648 -0.4627 0.230 Uiso 1 1 calc GR . . . .
H14B H -0.9375 -0.3811 -0.4787 0.230 Uiso 1 1 calc GR . . . .
H14C H -0.8948 -0.6478 -0.4552 0.230 Uiso 1 1 calc GR . . . .
C8 C -0.30360(19) -0.3744(9) -0.09270(15) 0.0618(8) Uani 1 1 d . . . . .
H8 H -0.3019 -0.1708 -0.0888 0.074 Uiso 1 1 calc R . . . .
C10 C -0.2558(2) -0.4985(13) -0.03475(17) 0.0810(13) Uani 1 1 d . . . . .
H10A H -0.2588 -0.6983 -0.0364 0.121 Uiso 1 1 calc GR . . . .
H10B H -0.2680 -0.4325 0.0030 0.121 Uiso 1 1 calc GR . . . .
H10C H -0.2107 -0.4424 -0.0346 0.121 Uiso 1 1 calc GR . . . .
C9 C -0.3749(2) -0.4671(15) -0.0957(2) 0.0892(16) Uani 1 1 d . . . . .
H9A H -0.4044 -0.3760 -0.1305 0.134 Uiso 1 1 calc GR . . . .
H9B H -0.3876 -0.4188 -0.0569 0.134 Uiso 1 1 calc GR . . . .
H9C H -0.3781 -0.6655 -0.1017 0.134 Uiso 1 1 calc GR . . . .
H3 H -0.7366(18) -0.729(5) -0.3747(17) 0.052(9) Uiso 1 1 d D . . . .
H2 H -0.372(2) -0.717(6) -0.240(2) 0.078(13) Uiso 1 1 d D . . . .
C7 C -0.28047(15) -0.4555(7) -0.15330(13) 0.0480(7) Uani 1 1 d . . . . .
H7 H -0.2804 -0.6595 -0.1562 0.058 Uiso 1 1 calc R . . . .
N1 N -0.21233(17) -0.3561(10) -0.15154(17) 0.0739(10) Uani 1 1 d D . . . .
H1C H -0.216(3) -0.159(5) -0.156(3) 0.094(18) Uiso 1 1 d D . . . .
H1D H -0.201(2) -0.432(10) -0.1882(17) 0.082(15) Uiso 1 1 d D . . . .
N4B N -0.8277(11) -0.574(8) -0.2845(12) 0.056(10) Uani 0.15(2) 1 d . U P A 2
H4AA H -0.8099(19) -0.240(6) -0.274(2) 0.055(12) Uiso 0.85(2) 1 d D . P A 1
H4AB H -0.806(2) -0.540(10) -0.251(4) 0.14(3) Uiso 0.85(2) 1 d D . 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
C6 N2 1.322(5) . ?
C6 O1 1.222(4) . ?
C6 C7 1.520(4) . ?
C11 N3 1.328(4) . ?
C11 O2 1.220(4) . ?
C11 C12 1.527(5) . ?
N2 C1 1.442(4) . ?
N2 H2 0.92(3) . ?
N3 C5 1.450(4) . ?
N3 H3 0.91(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.472(5) . ?
C2 C3 1.524(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.494(5) . ?
C12 H12 0.9800 . ?
C12 H12A 0.9800 . ?
C12 C13 1.513(5) . ?
C12 N4A 1.492(6) . ?
C12 N4B 1.27(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.521(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C13 H13 0.9800 . ?
C13 C15 1.536(7) . ?
C13 C14 1.527(8) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
N4A H4AA 0.952(13) . ?
N4A H4AB 0.959(13) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C8 H8 0.9800 . ?
C8 C10 1.532(6) . ?
C8 C9 1.511(6) . ?
C8 C7 1.539(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C7 H7 0.9800 . ?
C7 N1 1.464(4) . ?
N1 H1C 0.95(2) . ?
N1 H1D 0.95(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
N2 C6 C7 116.5(3) . . ?
O1 C6 N2 123.0(3) . . ?
O1 C6 C7 120.6(3) . . ?
N3 C11 C12 116.2(3) . . ?
O2 C11 N3 124.2(3) . . ?
O2 C11 C12 119.6(3) . . ?
C6 N2 C1 123.9(3) . . ?
C6 N2 H2 128(3) . . ?
C1 N2 H2 107(3) . . ?
C11 N3 C5 122.9(3) . . ?
C11 N3 H3 122(2) . . ?
C5 N3 H3 114(2) . . ?
H2A C2 H2B 107.7 . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C1 C2 C3 113.9(3) . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
N2 C1 C2 112.4(3) . . ?
N2 C1 H1A 109.1 . . ?
N2 C1 H1B 109.1 . . ?
C2 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.9 . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 C2 112.4(3) . . ?
C4 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C11 C12 H12 109.5 . . ?
C11 C12 H12A 97.5 . . ?
C13 C12 C11 110.7(3) . . ?
C13 C12 H12 109.5 . . ?
C13 C12 H12A 97.5 . . ?
N4A C12 C11 110.6(4) . . ?
N4A C12 H12 109.5 . . ?
N4A C12 C13 107.0(4) . . ?
N4B C12 C11 117.8(10) . . ?
N4B C12 H12A 97.5 . . ?
N4B C12 C13 126.4(12) . . ?
C3 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C3 C4 C5 113.4(3) . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
N3 C5 C4 110.3(3) . . ?
N3 C5 H5A 109.6 . . ?
N3 C5 H5B 109.6 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C12 C13 H13 109.3 . . ?
C12 C13 C15 111.4(4) . . ?
C12 C13 C14 108.4(5) . . ?
C15 C13 H13 109.3 . . ?
C14 C13 H13 109.3 . . ?
C14 C13 C15 109.2(4) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 N4A H4AA 95(3) . . ?
C12 N4A H4AB 101(6) . . ?
H4AA N4A H4AB 105.4(19) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C8 H8 108.2 . . ?
C10 C8 C7 110.0(3) . . ?
C9 C8 H8 108.2 . . ?
C9 C8 C10 110.9(4) . . ?
C9 C8 C7 111.2(3) . . ?
C7 C8 H8 108.2 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C7 C8 109.6(3) . . ?
C6 C7 H7 108.2 . . ?
C8 C7 H7 108.2 . . ?
N1 C7 C6 111.2(3) . . ?
N1 C7 C8 111.3(3) . . ?
N1 C7 H7 108.2 . . ?
C7 N1 H1C 106(3) . . ?
C7 N1 H1D 106(3) . . ?
H1C N1 H1D 108(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
C6 N2 C1 C2 -105.7(4) . . . . ?
C11 N3 C5 C4 94.4(4) . . . . ?
C11 C12 C13 C15 178.8(4) . . . . ?
C11 C12 C13 C14 58.7(6) . . . . ?
N2 C6 C7 C8 -109.8(3) . . . . ?
N2 C6 C7 N1 126.6(3) . . . . ?
N3 C11 C12 C13 -118.8(4) . . . . ?
N3 C11 C12 N4A 122.8(5) . . . . ?
N3 C11 C12 N4B 85(2) . . . . ?
O2 C11 N3 C5 3.2(5) . . . . ?
O2 C11 C12 C13 63.1(4) . . . . ?
O2 C11 C12 N4A -55.2(6) . . . . ?
O2 C11 C12 N4B -93(2) . . . . ?
C2 C3 C4 C5 -177.1(4) . . . . ?
O1 C6 N2 C1 -4.7(5) . . . . ?
O1 C6 C7 C8 71.2(4) . . . . ?
O1 C6 C7 N1 -52.3(4) . . . . ?
C1 C2 C3 C4 175.9(4) . . . . ?
C3 C2 C1 N2 -176.2(4) . . . . ?
C3 C4 C5 N3 175.5(3) . . . . ?
C12 C11 N3 C5 -174.8(3) . . . . ?
N4A C12 C13 C15 -60.6(6) . . . . ?
N4A C12 C13 C14 179.3(6) . . . . ?
C10 C8 C7 C6 177.5(3) . . . . ?
C10 C8 C7 N1 -59.1(4) . . . . ?
C9 C8 C7 C6 54.2(4) . . . . ?
C9 C8 C7 N1 177.7(4) . . . . ?
C7 C6 N2 C1 176.4(3) . . . . ?
N4B C12 C13 C15 -27(2) . . . . ?
N4B C12 C13 C14 -147(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_str1763
_database_code_depnum_ccdc_archive 'CCDC 1880522'
loop_
_audit_author_name
_audit_author_address
'Vicente Mart? Centelles'
;Universitat Jaume I
Spain
;
_audit_update_record             
;
2018-11-21 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_EXPT005_str1763             
;
PROBLEM: _exptl_crystal_description is missing
RESPONSE: No description was provided.
;
# Added during the CSD deposition process: Wednesday 21 November 2018 05:31 PM
# end Validation Reply Form

_audit_creation_date             2015-11-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H31 N5 O2'
_chemical_formula_sum            'C22 H31 N5 O2'
_chemical_formula_weight         397.52
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H31 N5 O2'
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 2 21 21'
_space_group_name_Hall           'P 2bc 2'
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                   5.01883(14)
_cell_length_b                   16.5007(5)
_cell_length_c                   25.5451(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2115.49(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3060
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3420
_cell_measurement_theta_min      4.3550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.6174
_exptl_crystal_size_mid          0.0395
_exptl_crystal_size_min          0.0248
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6701
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.497
_diffrn_reflns_theta_min         3.460
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4051
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   34.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680   38.0000 -120.0000 83

#__ type_ start__ end____ width___ exp.time_
  2 omega  -14.00   51.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0680  -57.0000   60.0000 65

#__ type_ start__ end____ width___ exp.time_
  3 omega   91.00  117.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0680  178.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  134.00  175.00   1.0000  175.0000
omega____ theta____ kappa____ phi______ frames
    -      101.3070  125.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
  5 omega   27.00   56.00   1.0000  175.0000
omega____ theta____ kappa____ phi______ frames
    -      101.3070  -45.0000  -60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega   24.00   89.00   1.0000  175.0000
omega____ theta____ kappa____ phi______ frames
    -      101.3070  -30.0000   60.0000 65

#__ type_ start__ end____ width___ exp.time_
  7 omega   39.00   89.00   1.0000  175.0000
omega____ theta____ kappa____ phi______ frames
    -      101.3070  -45.0000    0.0000 50

#__ type_ start__ end____ width___ exp.time_
  8 omega   30.00   91.00   1.0000  175.0000
omega____ theta____ kappa____ phi______ frames
    -      101.3070  -94.0000  -90.0000 61

#__ type_ start__ end____ width___ exp.time_
  9 omega   43.00   87.00   1.0000  175.0000
omega____ theta____ kappa____ phi______ frames
    -      101.3070  -30.0000  -60.0000 44

#__ type_ start__ end____ width___ exp.time_
 10 omega   46.00   86.00   1.0000  175.0000
omega____ theta____ kappa____ phi______ frames
    -      101.3070  -30.0000 -150.0000 40

#__ type_ start__ end____ width___ exp.time_
 11 omega  103.00  130.00   1.0000  175.0000
omega____ theta____ kappa____ phi______ frames
    -      101.3070  125.0000  120.0000 27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0139950000
_diffrn_orient_matrix_UB_12      -0.0388392000
_diffrn_orient_matrix_UB_13      0.0547532000
_diffrn_orient_matrix_UB_21      0.0795742000
_diffrn_orient_matrix_UB_22      0.0824050000
_diffrn_orient_matrix_UB_23      0.0236093000
_diffrn_orient_matrix_UB_31      -0.2962679000
_diffrn_orient_matrix_UB_32      0.0203501000
_diffrn_orient_matrix_UB_33      0.0089492000
_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_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.666
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.926
_reflns_number_gt                3560
_reflns_number_total             3869
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1314 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.13(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3869
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.038
_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)+(0.0547P)²+0.3338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1119
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N2-H2 = N4-H4 = N1-H1A = N1-H1B = N5-H5B = N5-H5A
 0.97 with sigma of 0.02
 N3-H3
 0.97 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C6(H6), C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C1(H1C,H1D), C2(H2A,H2B), C4(H4A,H4B), C7(H7A,H7B), C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C18(H18), C19(H19), C21(H21), C22(H22), C9(H9), C13(H13), C11(H11),
 C10(H10), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 -0.8274(3) -0.15295(13) -0.63763(7) 0.0385(4) Uani 1 1 d . . . . .
O2 O 0.2939(4) -0.28314(13) -0.90498(9) 0.0437(5) Uani 1 1 d . . . . .
N4 N -0.1427(4) -0.25232(13) -0.89774(8) 0.0311(4) Uani 1 1 d D . . . .
N2 N -0.3967(4) -0.15927(14) -0.66171(8) 0.0311(4) Uani 1 1 d D . . . .
N3 N -0.2776(5) -0.15448(16) -0.80557(8) 0.0381(5) Uani 1 1 d D . . . .
C14 C 0.0586(5) -0.30482(15) -0.90212(9) 0.0303(5) Uani 1 1 d . . . . .
C5 C -0.5900(5) -0.15532(15) -0.62587(9) 0.0282(5) Uani 1 1 d . . . . .
C17 C 0.0081(5) -0.41556(15) -0.80488(10) 0.0349(5) Uani 1 1 d . . . . .
N1 N -0.5721(6) -0.07398(15) -0.54476(10) 0.0468(6) Uani 1 1 d D . . . .
C3 C -0.0524(6) -0.13604(15) -0.83919(10) 0.0353(5) Uani 1 1 d . . . . .
H3A H 0.1061 -0.1622 -0.8256 0.042 Uiso 1 1 calc R . . . .
H3B H -0.0216 -0.0780 -0.8393 0.042 Uiso 1 1 calc R . . . .
N5 N 0.0778(6) -0.43255(15) -0.95272(9) 0.0465(6) Uani 1 1 d D . . . .
C1 C -0.4526(5) -0.16687(17) -0.71758(9) 0.0336(5) Uani 1 1 d . . . . .
H1C H -0.6158 -0.1380 -0.7257 0.040 Uiso 1 1 calc R . . . .
H1D H -0.4800 -0.2236 -0.7261 0.040 Uiso 1 1 calc R . . . .
C6 C -0.5036(5) -0.15136(16) -0.56858(9) 0.0337(5) Uani 1 1 d . . . . .
H6 H -0.3102 -0.1588 -0.5667 0.040 Uiso 1 1 calc R . . . .
C15 C -0.0118(5) -0.39455(15) -0.90416(10) 0.0331(5) Uani 1 1 d . . . . .
H15 H -0.2058 -0.4001 -0.9017 0.040 Uiso 1 1 calc R . . . .
C2 C -0.2292(5) -0.13373(16) -0.75086(10) 0.0345(6) Uani 1 1 d . . . . .
H2A H -0.2197 -0.0753 -0.7470 0.041 Uiso 1 1 calc R . . . .
H2B H -0.0607 -0.1566 -0.7396 0.041 Uiso 1 1 calc R . . . .
C8 C -0.5678(6) -0.30360(17) -0.55327(11) 0.0423(6) Uani 1 1 d . . . . .
C20 C -0.1855(7) -0.37584(18) -0.70568(12) 0.0446(6) Uani 1 1 d . . . . .
H20 H -0.2487 -0.3632 -0.6724 0.054 Uiso 1 1 calc R . . . .
C4 C -0.1027(6) -0.16485(16) -0.89478(10) 0.0367(6) Uani 1 1 d . . . . .
H4A H -0.2592 -0.1377 -0.9085 0.044 Uiso 1 1 calc R . . . .
H4B H 0.0479 -0.1500 -0.9166 0.044 Uiso 1 1 calc R . . . .
C7 C -0.6398(6) -0.21892(18) -0.53715(10) 0.0416(6) Uani 1 1 d . . . . .
H7A H -0.5947 -0.2121 -0.5005 0.050 Uiso 1 1 calc R . . . .
H7B H -0.8312 -0.2125 -0.5404 0.050 Uiso 1 1 calc R . . . .
C16 C 0.1150(6) -0.43910(17) -0.85785(11) 0.0395(6) Uani 1 1 d . . . . .
H16A H 0.0887 -0.4969 -0.8626 0.047 Uiso 1 1 calc R . . . .
H16B H 0.3054 -0.4290 -0.8583 0.047 Uiso 1 1 calc R . . . .
C18 C -0.2025(6) -0.45754(17) -0.78321(12) 0.0422(6) Uani 1 1 d . . . . .
H18 H -0.2809 -0.4994 -0.8021 0.051 Uiso 1 1 calc R . . . .
C19 C -0.2992(7) -0.4385(2) -0.73406(12) 0.0476(7) Uani 1 1 d . . . . .
H19 H -0.4405 -0.4678 -0.7200 0.057 Uiso 1 1 calc R . . . .
C21 C 0.0213(7) -0.33259(19) -0.72712(12) 0.0471(7) Uani 1 1 d . . . . .
H21 H 0.0968 -0.2899 -0.7085 0.057 Uiso 1 1 calc R . . . .
C22 C 0.1184(6) -0.35218(18) -0.77644(11) 0.0422(6) Uani 1 1 d . . . . .
H22 H 0.2587 -0.3226 -0.7906 0.051 Uiso 1 1 calc R . . . .
C9 C -0.7126(7) -0.3448(2) -0.59084(13) 0.0512(7) Uani 1 1 d . . . . .
H9 H -0.8560 -0.3194 -0.6070 0.061 Uiso 1 1 calc R . . . .
C13 C -0.3520(8) -0.3422(3) -0.53063(16) 0.0662(10) Uani 1 1 d . . . . .
H13 H -0.2518 -0.3155 -0.5053 0.079 Uiso 1 1 calc R . . . .
C11 C -0.4367(12) -0.4613(2) -0.5821(2) 0.0923(18) Uani 1 1 d . . . . .
H11 H -0.3946 -0.5144 -0.5911 0.111 Uiso 1 1 calc R . . . .
C10 C -0.6475(10) -0.4234(2) -0.60476(19) 0.0744(12) Uani 1 1 d . . . . .
H10 H -0.7486 -0.4504 -0.6298 0.089 Uiso 1 1 calc R . . . .
C12 C -0.2846(10) -0.4198(3) -0.5453(3) 0.0938(19) Uani 1 1 d . . . . .
H12 H -0.1363 -0.4447 -0.5305 0.113 Uiso 1 1 calc R . . . .
H2 H -0.225(5) -0.161(2) -0.6506(14) 0.045(9) Uiso 1 1 d D . . . .
H4 H -0.312(5) -0.273(2) -0.8990(15) 0.048(9) Uiso 1 1 d D . . . .
H5A H -0.031(8) -0.415(3) -0.9808(14) 0.070(12) Uiso 1 1 d D . . . .
H1A H -0.739(6) -0.055(2) -0.5588(16) 0.059(11) Uiso 1 1 d D . . . .
H5B H 0.253(6) -0.412(3) -0.9621(18) 0.075(14) Uiso 1 1 d D . . . .
H1B H -0.444(7) -0.034(2) -0.5531(18) 0.074(13) Uiso 1 1 d D . . . .
H3 H -0.306(8) -0.2118(15) -0.8096(16) 0.058(10) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.230(3) . ?
O2 C14 1.236(3) . ?
N4 C14 1.335(3) . ?
N4 C4 1.459(3) . ?
N4 H4 0.92(2) . ?
N2 C5 1.335(3) . ?
N2 C1 1.460(3) . ?
N2 H2 0.91(2) . ?
N3 C3 1.452(3) . ?
N3 C2 1.459(3) . ?
N3 H3 0.96(2) . ?
C14 C15 1.523(4) . ?
C5 C6 1.528(3) . ?
C17 C16 1.507(4) . ?
C17 C18 1.380(4) . ?
C17 C22 1.388(4) . ?
N1 C6 1.456(4) . ?
N1 H1A 0.97(2) . ?
N1 H1B 0.94(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.519(4) . ?
N5 C15 1.461(3) . ?
N5 H5A 0.95(2) . ?
N5 H5B 0.97(2) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C1 C2 1.510(4) . ?
C6 H6 0.9800 . ?
C6 C7 1.534(4) . ?
C15 H15 0.9800 . ?
C15 C16 1.531(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C8 C7 1.501(4) . ?
C8 C9 1.383(5) . ?
C8 C13 1.383(5) . ?
C20 H20 0.9300 . ?
C20 C19 1.386(5) . ?
C20 C21 1.374(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C18 H18 0.9300 . ?
C18 C19 1.382(4) . ?
C19 H19 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.389(4) . ?
C22 H22 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.383(5) . ?
C13 H13 0.9300 . ?
C13 C12 1.377(7) . ?
C11 H11 0.9300 . ?
C11 C10 1.359(8) . ?
C11 C12 1.391(9) . ?
C10 H10 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 N4 C4 122.8(2) . . ?
C14 N4 H4 117(2) . . ?
C4 N4 H4 120(2) . . ?
C5 N2 C1 122.3(2) . . ?
C5 N2 H2 118(2) . . ?
C1 N2 H2 119(2) . . ?
C3 N3 C2 112.8(2) . . ?
C3 N3 H3 105(2) . . ?
C2 N3 H3 111(3) . . ?
O2 C14 N4 122.7(2) . . ?
O2 C14 C15 120.1(2) . . ?
N4 C14 C15 117.3(2) . . ?
O1 C5 N2 122.5(2) . . ?
O1 C5 C6 120.5(2) . . ?
N2 C5 C6 116.9(2) . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 C22 118.3(3) . . ?
C22 C17 C16 121.5(3) . . ?
C6 N1 H1A 110(3) . . ?
C6 N1 H1B 111(3) . . ?
H1A N1 H1B 106(4) . . ?
N3 C3 H3A 109.4 . . ?
N3 C3 H3B 109.4 . . ?
N3 C3 C4 111.0(2) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C15 N5 H5A 109(3) . . ?
C15 N5 H5B 109(3) . . ?
H5A N5 H5B 103(4) . . ?
N2 C1 H1C 109.2 . . ?
N2 C1 H1D 109.2 . . ?
N2 C1 C2 112.1(2) . . ?
H1C C1 H1D 107.9 . . ?
C2 C1 H1C 109.2 . . ?
C2 C1 H1D 109.2 . . ?
C5 C6 H6 108.9 . . ?
C5 C6 C7 110.1(2) . . ?
N1 C6 C5 111.8(2) . . ?
N1 C6 H6 108.9 . . ?
N1 C6 C7 108.3(2) . . ?
C7 C6 H6 108.9 . . ?
C14 C15 H15 108.6 . . ?
C14 C15 C16 110.1(2) . . ?
N5 C15 C14 112.0(2) . . ?
N5 C15 H15 108.6 . . ?
N5 C15 C16 108.8(2) . . ?
C16 C15 H15 108.6 . . ?
N3 C2 C1 109.3(2) . . ?
N3 C2 H2A 109.8 . . ?
N3 C2 H2B 109.8 . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
C9 C8 C7 121.5(3) . . ?
C9 C8 C13 118.4(3) . . ?
C13 C8 C7 120.2(3) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C21 C20 C19 119.4(3) . . ?
N4 C4 C3 112.4(2) . . ?
N4 C4 H4A 109.1 . . ?
N4 C4 H4B 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
C6 C7 H7A 108.5 . . ?
C6 C7 H7B 108.5 . . ?
C8 C7 C6 115.2(2) . . ?
C8 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C17 C16 C15 115.0(2) . . ?
C17 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
C15 C16 H16A 108.5 . . ?
C15 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C19 121.3(3) . . ?
C19 C18 H18 119.3 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 C20 120.0(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.4(3) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 120.7(3) . . ?
C17 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.0(4) . . ?
C10 C9 H9 119.5 . . ?
C8 C13 H13 119.8 . . ?
C12 C13 C8 120.5(5) . . ?
C12 C13 H13 119.8 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.3(4) . . ?
C12 C11 H11 120.4 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(5) . . ?
C11 C10 H10 119.8 . . ?
C13 C12 C11 120.4(4) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?

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 C5 C6 N1 -64.6(3) . . . . ?
O1 C5 C6 C7 55.8(3) . . . . ?
O2 C14 C15 N5 -59.5(3) . . . . ?
O2 C14 C15 C16 61.7(3) . . . . ?
N4 C14 C15 N5 119.9(3) . . . . ?
N4 C14 C15 C16 -118.9(2) . . . . ?
N2 C5 C6 N1 113.7(3) . . . . ?
N2 C5 C6 C7 -125.9(2) . . . . ?
N2 C1 C2 N3 171.2(2) . . . . ?
N3 C3 C4 N4 -60.9(3) . . . . ?
C14 N4 C4 C3 -86.2(3) . . . . ?
C14 C15 C16 C17 66.2(3) . . . . ?
C5 N2 C1 C2 154.5(2) . . . . ?
C5 C6 C7 C8 63.4(3) . . . . ?
C17 C18 C19 C20 0.5(5) . . . . ?
N1 C6 C7 C8 -174.2(2) . . . . ?
C3 N3 C2 C1 -170.9(2) . . . . ?
N5 C15 C16 C17 -170.7(2) . . . . ?
C1 N2 C5 O1 -4.4(4) . . . . ?
C1 N2 C5 C6 177.3(2) . . . . ?
C2 N3 C3 C4 175.4(2) . . . . ?
C8 C9 C10 C11 -0.8(6) . . . . ?
C8 C13 C12 C11 -1.7(6) . . . . ?
C20 C21 C22 C17 0.1(5) . . . . ?
C4 N4 C14 O2 -1.4(4) . . . . ?
C4 N4 C14 C15 179.3(2) . . . . ?
C7 C8 C9 C10 -178.9(3) . . . . ?
C7 C8 C13 C12 -179.9(3) . . . . ?
C16 C17 C18 C19 178.2(3) . . . . ?
C16 C17 C22 C21 -178.5(3) . . . . ?
C18 C17 C16 C15 91.4(3) . . . . ?
C18 C17 C22 C21 1.0(4) . . . . ?
C19 C20 C21 C22 -0.9(5) . . . . ?
C21 C20 C19 C18 0.6(5) . . . . ?
C22 C17 C16 C15 -89.1(3) . . . . ?
C22 C17 C18 C19 -1.3(4) . . . . ?
C9 C8 C7 C6 -90.5(3) . . . . ?
C9 C8 C13 C12 -0.1(5) . . . . ?
C13 C8 C7 C6 89.3(3) . . . . ?
C13 C8 C9 C10 1.4(5) . . . . ?
C10 C11 C12 C13 2.2(7) . . . . ?
C12 C11 C10 C9 -1.0(6) . . . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 -8 -10 0.0059 0.0090 -8.0353 -9.9775 -0.2341 -0.8970 -0.2555
0 8 10 0.0189 -0.0090 8.0353 9.9775 0.2341 0.8970 0.2555
-3 0 0 0.3086 -2.9956 0.0129 -0.0541 -0.0454 -0.2386 0.8873
3 0 0 0.3086 2.9956 -0.0129 0.0541 0.0454 0.2386 -0.8873
0 3 -16 0.0134 0.0091 2.9423 -16.0504 -0.9930 -0.1358 -0.0865
0 -3 16 0.0134 -0.0091 -2.9423 16.0504 0.9930 0.1358 0.0865

_olex2_submission_special_instructions 'No special instructions were received'
