# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1952629'
loop_
_audit_author_name
_audit_author_address
'Jeppe Christensen '
;national crystallography service (southampton) and diamond light source (didcot)
United Kingdom
;
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H20 N4 O3'
_chemical_formula_sum            'C15 H20 N4 O3'
_chemical_formula_weight         304.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.5616(3)
_cell_length_b                   17.9003(13)
_cell_length_c                   15.5410(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.111(5)
_cell_angle_gamma                90
_cell_volume                     1543.19(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10190
_cell_measurement_theta_min      2.2650
_cell_measurement_theta_max      29.6730

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_T_min  0.47050
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_collimation    '0.07 mm Confocal mirrors, HF Varimax'
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_source                   'rotating anode'
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source_target            Mo
_diffrn_source_type              'FR-E+ SuperBright rotating anode'
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12'
_diffrn_measurement_method       'profile data from ω scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 14.286
_diffrn_reflns_number            30287
_diffrn_reflns_av_unetI/netI     0.1168
_diffrn_reflns_av_R_equivalents  0.0855
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.276
_diffrn_reflns_theta_max         30.051
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8146
_reflns_number_gt                4529
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_max     0.863
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    
'SHELXT (G. M. Sheldrick Acta Cryst. (2015). A71, 3-8)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0532P)²+0.3399P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration syn
_refine_ls_number_reflns         8146
_refine_ls_number_parameters     423
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1515
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.1447
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.3423(5) 0.56691(19) -0.07194(19) 0.0307(8) Uani 1 1 d . . . . .
O3 O -0.0555(5) 0.5682(2) -0.05565(18) 0.0287(8) Uani 1 1 d . . . . .
O6 O 0.5896(5) 0.4228(2) 0.5571(2) 0.0389(9) Uani 1 1 d . . . . .
O5 O 0.1952(5) 0.4175(2) 0.5778(2) 0.0386(9) Uani 1 1 d . . . . .
O4 O -0.2627(6) 0.3408(2) 0.2807(2) 0.0471(10) Uani 1 1 d . . . . .
N4 N 0.1826(6) 0.6061(2) 0.0560(2) 0.0227(8) Uani 1 1 d . . . . .
N2 N 0.3889(7) 0.6322(2) 0.1850(2) 0.0301(10) Uani 1 1 d . . . . .
N3 N 0.6103(7) 0.6045(3) 0.0686(3) 0.0307(10) Uani 1 1 d . . . . .
N6 N 0.1375(7) 0.3574(2) 0.3190(2) 0.0288(10) Uani 1 1 d . . . . .
C8 C 0.1765(7) 0.5803(3) -0.0266(3) 0.0226(10) Uani 1 1 d . . . . .
O1 O 0.7892(6) 0.6274(3) 0.2300(2) 0.0679(15) Uani 1 1 d . . . . .
N7 N -0.0769(6) 0.3755(3) 0.4398(3) 0.0343(10) Uani 1 1 d . . . . .
C7 C 0.3969(7) 0.6140(3) 0.0981(3) 0.0235(10) Uani 1 1 d . . . . .
N8 N 0.3494(6) 0.3853(3) 0.4458(2) 0.0329(11) Uani 1 1 d . . . . .
C21 C -0.0560(8) 0.3439(3) 0.2612(3) 0.0305(12) Uani 1 1 d . . . . .
N5 N 0.2421(7) 0.3628(2) 0.1538(2) 0.0415(10) Uani 1 1 d . . . . .
C20 C 0.0116(9) 0.3310(3) 0.1699(3) 0.0332(12) Uani 1 1 d . . . . .
H20 H -0.1155 0.3528 0.1285 0.040 Uiso 1 1 calc R U . . .
C27 C 0.3843(10) 0.6486(3) 0.6705(4) 0.0464(16) Uani 1 1 d . . . . .
H27 H 0.2501 0.6716 0.6943 0.056 Uiso 1 1 calc R U . . .
C15 C 0.1166(9) 0.4143(3) -0.1702(4) 0.0433(15) Uani 1 1 d . . . . .
H15 H 0.2361 0.4421 -0.1970 0.052 Uiso 1 1 calc R U . . .
C25 C 0.6049(8) 0.5377(3) 0.6401(3) 0.0356(15) Uani 1 1 d . . . . .
C9 C -0.0966(8) 0.5340(3) -0.1401(3) 0.0331(13) Uani 1 1 d . . . . .
H9A H 0.0210 0.5542 -0.1789 0.040 Uiso 1 1 calc R U . . .
H9B H -0.2603 0.5471 -0.1646 0.040 Uiso 1 1 calc R U . . .
C23 C 0.3567(7) 0.4090(3) 0.5295(3) 0.0304(12) Uani 1 1 d . . . . .
C22 C 0.1342(7) 0.3731(3) 0.4065(3) 0.0270(11) Uani 1 1 d . . . . .
N1 N 0.2823(8) 0.6830(3) 0.3416(3) 0.0581(14) Uani 1 1 d . . . . .
C10 C -0.0729(8) 0.4511(3) -0.1361(3) 0.0285(12) Uani 1 1 d . . . . .
C28 C 0.5516(9) 0.6917(4) 0.6318(4) 0.0467(16) Uani 1 1 d . . . . .
H28 H 0.5327 0.7444 0.6286 0.056 Uiso 1 1 calc R U . . .
C12 C -0.2186(9) 0.3312(4) -0.0904(3) 0.0440(15) Uani 1 1 d . . . . .
H12 H -0.3339 0.3031 -0.0618 0.053 Uiso 1 1 calc R U . . .
C24 C 0.6320(9) 0.4543(3) 0.6432(3) 0.0420(15) Uani 1 1 d . . . . .
H24A H 0.7965 0.4412 0.6669 0.050 Uiso 1 1 calc R U . . .
H24B H 0.5154 0.4329 0.6816 0.050 Uiso 1 1 calc R U . . .
C13 C -0.0327(9) 0.2949(3) -0.1266(3) 0.0373(14) Uani 1 1 d . . . . .
H13 H -0.0200 0.2420 -0.1247 0.045 Uiso 1 1 calc R U . . .
C11 C -0.2397(9) 0.4078(4) -0.0950(4) 0.0431(15) Uani 1 1 d . . . . .
H11 H -0.3701 0.4316 -0.0698 0.052 Uiso 1 1 calc R U . . .
C17 C 0.3381(10) 0.3197(4) 0.0861(4) 0.0536(17) Uani 1 1 d . . . . .
H17A H 0.5139 0.3275 0.0843 0.064 Uiso 1 1 calc R U . . .
H17B H 0.2570 0.3322 0.0291 0.064 Uiso 1 1 calc R U . . .
C26 C 0.4119(9) 0.5726(4) 0.6747(3) 0.0427(14) Uani 1 1 d . . . . .
H26 H 0.2966 0.5433 0.7019 0.051 Uiso 1 1 calc R U . . .
C6 C 0.5803(9) 0.6344(4) 0.2461(3) 0.0441(15) Uani 1 1 d . . . . .
C19 C 0.0418(11) 0.2459(3) 0.1498(4) 0.0580(18) Uani 1 1 d . . . . .
H19A H 0.0399 0.2156 0.2031 0.070 Uiso 1 1 calc R U . . .
H19B H -0.0883 0.2282 0.1079 0.070 Uiso 1 1 calc R U . . .
C30 C 0.7718(9) 0.5821(4) 0.6030(4) 0.0528(18) Uani 1 1 d . . . . .
H30 H 0.9083 0.5595 0.5803 0.063 Uiso 1 1 calc R U . . .
C29 C 0.7451(10) 0.6582(4) 0.5980(4) 0.061(2) Uani 1 1 d . . . . .
H29 H 0.8606 0.6876 0.5712 0.073 Uiso 1 1 calc R U . . .
C14 C 0.1338(10) 0.3373(4) -0.1655(4) 0.0507(17) Uani 1 1 d . . . . .
H14 H 0.2647 0.3131 -0.1901 0.061 Uiso 1 1 calc R U . . .
C16 C 0.2279(14) 0.4406(3) 0.1311(4) 0.078(2) Uani 1 1 d . . . . .
H16A H 0.1102 0.4473 0.0817 0.116 Uiso 1 1 calc R U . . .
H16B H 0.3864 0.4580 0.1158 0.116 Uiso 1 1 calc R U . . .
H16C H 0.1776 0.4695 0.1803 0.116 Uiso 1 1 calc R U . . .
C1 C 0.3181(14) 0.7631(4) 0.3435(5) 0.091(3) Uani 1 1 d . . . . .
H1A H 0.3666 0.7800 0.2873 0.136 Uiso 1 1 calc R U . . .
H1B H 0.4445 0.7757 0.3884 0.136 Uiso 1 1 calc R U . . .
H1C H 0.1674 0.7878 0.3562 0.136 Uiso 1 1 calc R U . . .
C5 C 0.5041(10) 0.6426(4) 0.3374(3) 0.0556(19) Uani 1 1 d . . . . .
H5 H 0.6349 0.6678 0.3743 0.067 Uiso 1 1 calc R U . . .
C4 C 0.4504(11) 0.5639(4) 0.3753(3) 0.070(2) Uani 1 1 d . . . . .
H4A H 0.4486 0.5252 0.3297 0.084 Uiso 1 1 calc R U . . .
H4B H 0.5742 0.5504 0.4217 0.084 Uiso 1 1 calc R U . . .
C2 C 0.1738(11) 0.6546(5) 0.4179(4) 0.086(3) Uani 1 1 d . . . . .
H2A H 0.0003 0.6673 0.4167 0.103 Uiso 1 1 calc R U . . .
H2B H 0.2570 0.6744 0.4715 0.103 Uiso 1 1 calc R U . . .
C3 C 0.2113(13) 0.5703(7) 0.4099(6) 0.134(5) Uani 1 1 d . . . . .
H3A H 0.2094 0.5456 0.4668 0.161 Uiso 1 1 calc R U . . .
H3B H 0.0849 0.5478 0.3699 0.161 Uiso 1 1 calc R U . . .
C18 C 0.2818(12) 0.2411(4) 0.1125(5) 0.079(2) Uani 1 1 d . . . . .
H18A H 0.2742 0.2073 0.0620 0.095 Uiso 1 1 calc R U . . .
H18B H 0.4062 0.2224 0.1560 0.095 Uiso 1 1 calc R U . . .
H53 H -0.215(8) 0.372(2) 0.406(3) 0.023(11) Uiso 1 1 d . . . . .
H52 H 0.243(9) 0.635(3) 0.207(3) 0.034(14) Uiso 1 1 d . . . . .
H50 H 0.620(7) 0.593(2) 0.012(3) 0.020(12) Uiso 1 1 d . . . . .
H51 H 0.747(12) 0.611(4) 0.111(4) 0.09(2) Uiso 1 1 d . . . . .
H55 H 0.280(10) 0.351(3) 0.299(4) 0.06(2) Uiso 1 1 d . . . . .
H54 H -0.067(11) 0.390(4) 0.507(5) 0.10(2) 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 C8 1.223(5) . ?
O3 C8 1.353(5) . ?
O3 C9 1.451(5) . ?
O6 C23 1.357(5) . ?
O6 C24 1.456(5) . ?
O5 C23 1.221(5) . ?
O4 C21 1.211(6) . ?
N4 C7 1.325(5) . ?
N4 C8 1.363(5) . ?
N2 C6 1.375(6) . ?
N2 C7 1.394(6) . ?
N2 H52 0.90(5) . ?
N3 C7 1.313(6) . ?
N3 H50 0.91(4) . ?
N3 H51 0.97(7) . ?
N6 C21 1.373(5) . ?
N6 C22 1.389(6) . ?
N6 H55 0.88(6) . ?
O1 C6 1.212(6) . ?
N7 C22 1.317(6) . ?
N7 H53 0.90(4) . ?
N7 H54 1.07(7) . ?
N8 C22 1.322(5) . ?
N8 C23 1.367(6) . ?
C21 C20 1.511(7) . ?
N5 C16 1.438(7) . ?
N5 C17 1.438(7) . ?
N5 C20 1.441(6) . ?
C20 C19 1.567(8) . ?
C20 H20 1.0000 . ?
C27 C26 1.370(8) . ?
C27 C28 1.379(8) . ?
C27 H27 0.9500 . ?
C15 C10 1.380(7) . ?
C15 C14 1.383(8) . ?
C15 H15 0.9500 . ?
C25 C30 1.380(8) . ?
C25 C26 1.384(7) . ?
C25 C24 1.501(8) . ?
C9 C10 1.490(8) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N1 C5 1.435(8) . ?
N1 C1 1.448(9) . ?
N1 C2 1.460(7) . ?
C10 C11 1.398(7) . ?
C28 C29 1.369(8) . ?
C28 H28 0.9500 . ?
C12 C13 1.376(8) . ?
C12 C11 1.377(8) . ?
C12 H12 0.9500 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C13 C14 1.371(7) . ?
C13 H13 0.9500 . ?
C11 H11 0.9500 . ?
C17 C18 1.504(10) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C26 H26 0.9500 . ?
C6 C5 1.516(7) . ?
C19 C18 1.496(8) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C30 C29 1.372(9) . ?
C30 H30 0.9500 . ?
C29 H29 0.9500 . ?
C14 H14 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C5 C4 1.565(9) . ?
C5 H5 1.0000 . ?
C4 C3 1.474(9) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C2 C3 1.529(13) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O3 C9 116.9(3) . . ?
C23 O6 C24 116.6(4) . . ?
C7 N4 C8 117.5(4) . . ?
C6 N2 C7 126.8(4) . . ?
C6 N2 H52 114(3) . . ?
C7 N2 H52 118(3) . . ?
C7 N3 H50 119(2) . . ?
C7 N3 H51 116(4) . . ?
H50 N3 H51 126(5) . . ?
C21 N6 C22 127.7(4) . . ?
C21 N6 H55 116(4) . . ?
C22 N6 H55 116(4) . . ?
O2 C8 O3 121.1(4) . . ?
O2 C8 N4 129.8(4) . . ?
O3 C8 N4 109.1(3) . . ?
C22 N7 H53 121(3) . . ?
C22 N7 H54 114(4) . . ?
H53 N7 H54 124(4) . . ?
N3 C7 N4 128.1(4) . . ?
N3 C7 N2 117.4(4) . . ?
N4 C7 N2 114.4(4) . . ?
C22 N8 C23 117.1(4) . . ?
O4 C21 N6 123.9(5) . . ?
O4 C21 C20 122.2(4) . . ?
N6 C21 C20 113.9(4) . . ?
C16 N5 C17 110.9(5) . . ?
C16 N5 C20 113.0(5) . . ?
C17 N5 C20 107.2(4) . . ?
N5 C20 C21 112.8(4) . . ?
N5 C20 C19 103.9(4) . . ?
C21 C20 C19 111.9(4) . . ?
N5 C20 H20 109.4 . . ?
C21 C20 H20 109.4 . . ?
C19 C20 H20 109.4 . . ?
C26 C27 C28 119.9(6) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C10 C15 C14 120.5(5) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C30 C25 C26 117.8(6) . . ?
C30 C25 C24 121.1(5) . . ?
C26 C25 C24 121.0(6) . . ?
O3 C9 C10 112.1(4) . . ?
O3 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
O3 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
O5 C23 O6 120.8(4) . . ?
O5 C23 N8 130.6(4) . . ?
O6 C23 N8 108.6(4) . . ?
N7 C22 N8 128.0(4) . . ?
N7 C22 N6 117.8(4) . . ?
N8 C22 N6 114.2(4) . . ?
C5 N1 C1 112.4(5) . . ?
C5 N1 C2 105.6(5) . . ?
C1 N1 C2 113.1(6) . . ?
C15 C10 C11 117.4(5) . . ?
C15 C10 C9 121.8(5) . . ?
C11 C10 C9 120.8(5) . . ?
C29 C28 C27 119.7(7) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C13 C12 C11 120.9(6) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
O6 C24 C25 110.3(4) . . ?
O6 C24 H24A 109.6 . . ?
C25 C24 H24A 109.6 . . ?
O6 C24 H24B 109.6 . . ?
C25 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
C14 C13 C12 118.0(5) . . ?
C14 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
C12 C11 C10 121.3(5) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
N5 C17 C18 102.0(5) . . ?
N5 C17 H17A 111.4 . . ?
C18 C17 H17A 111.4 . . ?
N5 C17 H17B 111.4 . . ?
C18 C17 H17B 111.4 . . ?
H17A C17 H17B 109.2 . . ?
C27 C26 C25 121.1(6) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
O1 C6 N2 124.1(5) . . ?
O1 C6 C5 122.6(4) . . ?
N2 C6 C5 113.2(5) . . ?
C18 C19 C20 104.1(5) . . ?
C18 C19 H19A 110.9 . . ?
C20 C19 H19A 110.9 . . ?
C18 C19 H19B 110.9 . . ?
C20 C19 H19B 110.9 . . ?
H19A C19 H19B 109.0 . . ?
C29 C30 C25 121.4(6) . . ?
C29 C30 H30 119.3 . . ?
C25 C30 H30 119.3 . . ?
C28 C29 C30 119.9(6) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C13 C14 C15 121.9(5) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?
N5 C16 H16A 109.5 . . ?
N5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C5 C6 113.0(4) . . ?
N1 C5 C4 104.4(4) . . ?
C6 C5 C4 109.8(5) . . ?
N1 C5 H5 109.9 . . ?
C6 C5 H5 109.9 . . ?
C4 C5 H5 109.9 . . ?
C3 C4 C5 105.6(6) . . ?
C3 C4 H4A 110.6 . . ?
C5 C4 H4A 110.6 . . ?
C3 C4 H4B 110.6 . . ?
C5 C4 H4B 110.6 . . ?
H4A C4 H4B 108.8 . . ?
N1 C2 C3 102.2(6) . . ?
N1 C2 H2A 111.3 . . ?
C3 C2 H2A 111.3 . . ?
N1 C2 H2B 111.3 . . ?
C3 C2 H2B 111.3 . . ?
H2A C2 H2B 109.2 . . ?
C4 C3 C2 103.8(7) . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
C2 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C19 C18 C17 105.2(5) . . ?
C19 C18 H18A 110.7 . . ?
C17 C18 H18A 110.7 . . ?
C19 C18 H18B 110.7 . . ?
C17 C18 H18B 110.7 . . ?
H18A C18 H18B 108.8 . . ?

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.048

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

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1952630'
loop_
_audit_author_name
_audit_author_address
'Jeppe Christensen '
;national crystallography service (southampton) and diamond light source (didcot)
United Kingdom
;
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H22 N4 O'
_chemical_formula_sum            'C19 H22 N4 O'
_chemical_formula_weight         322.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0010 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.27490(10)
_cell_length_b                   9.89550(10)
_cell_length_c                   21.8743(3)
_cell_angle_alpha                82.1070(10)
_cell_angle_beta                 86.6940(10)
_cell_angle_gamma                85.7750(10)
_cell_volume                     1767.32(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    30(2)
_cell_measurement_reflns_used    7932
_cell_measurement_theta_max      35.040975573
_cell_measurement_theta_min      0.903349717326

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_T_min  0.994168456942
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CCP4 7.0.035: AIMLESS, version 0.5.31 : 12/12/16
Scaling & analysis of unmerged intensities, 
absorption correction using spherical harmonics
;
_diffrn_ambient_temperature      30(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_dtime           0.004
_diffrn_detector_type            'Dectris, PILATUS 2M'
_diffrn_measurement_details      
;Data collection strategy using shutter-less operation of detector. 
Three omega scans -170 to 25 with phi 0, 120 and 240 respectively.
0.1 degree images with 0.5 sec exposure
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_details 'custom build fixed Chi diffractometer'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_radiation_collimation    'focusing mirrors and 0.0100 mm pinhole'
_diffrn_radiation_monochromator  'Si 111, double crystal monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_source_type              'DLS beamline I19, undulator'
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_wavelength_determination estimated

_diffrn_radiation_wavelength_details 'Zr absorption edge'
_diffrn_reflns_number            30477
_diffrn_reflns_av_unetI/netI     0.0995
_diffrn_reflns_av_R_equivalents  0.0939
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.824
_diffrn_reflns_theta_max         35.874
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             15842
_reflns_number_gt                14238
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'GDA 8.44; generic data acquisition software'
_computing_cell_refinement       
'XIA2 0.4.0.438-g4431aaa, Winter, G. (2010) J. Appl. Cryst. 43'
_computing_data_reduction        
'XIA2 0.4.0.438-g4431aaa, Winter, G. (2010) J. Appl. Cryst. 43'
_computing_structure_solution    'SHELXT Acta Cryst. (2015). A71, 3-8'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0336P)²+0.7768P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         15842
_refine_ls_number_parameters     551
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0817
_refine_ls_wR_factor_ref         0.2295
_refine_ls_wR_factor_gt          0.2260
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.162
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.44572(14) 0.30146(13) 0.93169(5) 0.0341(2) Uani 1 1 d . . . . .
O2 O 1.01147(14) 0.80380(13) 0.43749(6) 0.0364(2) Uani 1 1 d . . . . .
N3 N 0.77248(15) 0.28198(12) 0.91468(5) 0.0265(2) Uani 1 1 d . . . . .
N2 N 0.62716(14) 0.24324(12) 1.00862(5) 0.0271(2) Uani 1 1 d . . . . .
N7 N 0.53647(15) 0.72979(12) 0.51369(5) 0.0281(2) Uani 1 1 d . . . . .
N8 N 0.68994(15) 0.81170(12) 0.42381(6) 0.0289(2) Uani 1 1 d . . . . .
N6 N 0.81862(15) 0.74868(13) 0.51576(6) 0.0318(2) Uani 1 1 d . . . . .
N4 N 0.91342(14) 0.23269(12) 1.00646(5) 0.0266(2) Uani 1 1 d . . . . .
C7 C 0.78065(16) 0.25250(12) 0.97742(6) 0.0254(2) Uani 1 1 d . . . . .
C8 C 0.89724(16) 0.30244(12) 0.86888(6) 0.0257(2) Uani 1 1 d . . . . .
C26 C 0.67143(17) 0.76271(13) 0.48522(6) 0.0276(2) Uani 1 1 d . . . . .
C14 C 0.89700(16) 0.20290(13) 1.07204(6) 0.0264(2) Uani 1 1 d . . . . .
C33 C 0.57400(16) 0.83977(12) 0.37840(6) 0.0262(2) Uani 1 1 d . . . . .
C6 C 0.47528(17) 0.26605(14) 0.98632(6) 0.0281(2) Uani 1 1 d . . . . .
C27 C 0.54007(17) 0.68291(13) 0.57802(6) 0.0273(2) Uani 1 1 d . . . . .
C34 C 0.40609(16) 0.83685(13) 0.38992(6) 0.0273(2) Uani 1 1 d . . . . .
H34 H 0.3621 0.8129 0.4307 0.033 Uiso 1 1 calc R U . . .
C12 C 1.17225(18) 0.33892(14) 0.83014(6) 0.0299(2) Uani 1 1 d . . . . .
H12 H 1.2828 0.3468 0.8378 0.036 Uiso 1 1 calc R U . . .
C13 C 1.06024(17) 0.31383(13) 0.88010(6) 0.0274(2) Uani 1 1 d . . . . .
H13 H 1.0945 0.3046 0.9213 0.033 Uiso 1 1 calc R U . . .
C19 C 0.86937(18) 0.30790(14) 1.10900(6) 0.0290(2) Uani 1 1 d . . . . .
H19 H 0.8611 0.4005 1.0903 0.035 Uiso 1 1 calc R U . . .
C9 C 0.84933(18) 0.31482(14) 0.80746(6) 0.0288(2) Uani 1 1 d . . . . .
H9 H 0.7391 0.3063 0.7996 0.035 Uiso 1 1 calc R U . . .
C38 C 0.63606(17) 0.87446(14) 0.31753(6) 0.0286(2) Uani 1 1 d . . . . .
H38 H 0.7500 0.8756 0.3095 0.034 Uiso 1 1 calc R U . . .
C36 C 0.36521(18) 0.90501(14) 0.28035(6) 0.0294(2) Uani 1 1 d . . . . .
H36 H 0.2939 0.9274 0.2474 0.035 Uiso 1 1 calc R U . . .
C11 C 1.12448(19) 0.35263(15) 0.76932(6) 0.0312(3) Uani 1 1 d . . . . .
H11 H 1.2014 0.3707 0.7358 0.037 Uiso 1 1 calc R U . . .
C35 C 0.30382(17) 0.86970(14) 0.34052(6) 0.0288(2) Uani 1 1 d . . . . .
H35 H 0.1898 0.8678 0.3483 0.035 Uiso 1 1 calc R U . . .
C10 C 0.96218(19) 0.33947(15) 0.75842(6) 0.0312(3) Uani 1 1 d . . . . .
H10 H 0.9287 0.3474 0.7172 0.037 Uiso 1 1 calc R U . . .
C18 C 0.8539(2) 0.27719(16) 1.17324(7) 0.0326(3) Uani 1 1 d . . . . .
H18 H 0.8347 0.3489 1.1980 0.039 Uiso 1 1 calc R U . . .
C37 C 0.53288(18) 0.90715(14) 0.26898(6) 0.0299(2) Uani 1 1 d . . . . .
H37 H 0.5764 0.9309 0.2281 0.036 Uiso 1 1 calc R U . . .
C17 C 0.8665(2) 0.14139(16) 1.20119(7) 0.0335(3) Uani 1 1 d . . . . .
H17 H 0.8548 0.1205 1.2449 0.040 Uiso 1 1 calc R U . . .
C15 C 0.91186(19) 0.06643(14) 1.10015(6) 0.0300(2) Uani 1 1 d . . . . .
H15 H 0.9323 -0.0054 1.0755 0.036 Uiso 1 1 calc R U . . .
C25 C 0.97307(18) 0.76649(15) 0.49223(7) 0.0320(3) Uani 1 1 d . . . . .
C29 C 0.54624(19) 0.49697(14) 0.66282(7) 0.0309(2) Uani 1 1 d . . . . .
H29 H 0.5518 0.4017 0.6770 0.037 Uiso 1 1 calc R U . . .
C30 C 0.5371(2) 0.59038(15) 0.70549(7) 0.0330(3) Uani 1 1 d . . . . .
H30 H 0.5362 0.5591 0.7485 0.040 Uiso 1 1 calc R U . . .
C28 C 0.54731(18) 0.54237(14) 0.59942(6) 0.0290(2) Uani 1 1 d . . . . .
H28 H 0.5529 0.4780 0.5708 0.035 Uiso 1 1 calc R U . . .
C16 C 0.8966(2) 0.03640(15) 1.16450(7) 0.0329(3) Uani 1 1 d . . . . .
H16 H 0.9066 -0.0560 1.1834 0.039 Uiso 1 1 calc R U . . .
C32 C 0.5308(2) 0.77590(15) 0.62111(7) 0.0376(3) Uani 1 1 d . . . . .
H32 H 0.5255 0.8713 0.6072 0.045 Uiso 1 1 calc R U . . .
C31 C 0.5294(3) 0.72957(17) 0.68436(8) 0.0411(4) Uani 1 1 d . . . . .
H31 H 0.5231 0.7937 0.7131 0.049 Uiso 1 1 calc R U . . .
C5 C 0.348(2) 0.244(2) 1.0379(10) 0.0260(12) Uani 0.587(3) 1 d . . P A 1
H5 H 0.2559 0.1992 1.0230 0.031 Uiso 0.587(3) 1 calc R U P A 1
C24 C 1.0926(7) 0.7329(9) 0.5425(4) 0.0280(7) Uani 0.714(3) 1 d . . P A 1
H24 H 1.1826 0.7962 0.5356 0.034 Uiso 0.714(3) 1 calc R U P A 1
N5 N 1.0156(2) 0.7331(2) 0.60677(9) 0.0275(4) Uani 0.587(3) 1 d . . P A 1
C20 C 1.0141(4) 0.8654(3) 0.62906(13) 0.0330(5) Uani 0.587(3) 1 d . . P A 1
H20A H 0.9591 0.8602 0.6701 0.050 Uiso 0.587(3) 1 calc R U P A 1
H20B H 0.9564 0.9350 0.6005 0.050 Uiso 0.587(3) 1 calc R U P A 1
H20C H 1.1259 0.8901 0.6316 0.050 Uiso 0.587(3) 1 calc R U P A 1
C21 C 1.0928(3) 0.6189(2) 0.64747(11) 0.0305(5) Uani 0.587(3) 1 d . . P A 1
H21A H 1.0243 0.5942 0.6854 0.037 Uiso 0.587(3) 1 calc R U P A 1
H21B H 1.2009 0.6407 0.6591 0.037 Uiso 0.587(3) 1 calc R U P A 1
C22 C 1.1062(10) 0.5054(10) 0.6063(4) 0.0338(12) Uani 0.587(3) 1 d . . P A 1
H22A H 1.0004 0.4659 0.6045 0.041 Uiso 0.587(3) 1 calc R U P A 1
H22B H 1.1877 0.4316 0.6212 0.041 Uiso 0.587(3) 1 calc R U P A 1
C23 C 1.1611(3) 0.5814(2) 0.54272(11) 0.0286(4) Uani 0.587(3) 1 d . . P A 1
H23A H 1.1168 0.5408 0.5088 0.034 Uiso 0.587(3) 1 calc R U P A 1
H23B H 1.2809 0.5764 0.5375 0.034 Uiso 0.587(3) 1 calc R U P A 1
C1 C 0.3832(4) 0.0191(3) 1.09567(13) 0.0312(5) Uani 0.714(3) 1 d . . P A 1
H1A H 0.2679 0.0036 1.0944 0.047 Uiso 0.714(3) 1 calc R U P A 1
H1B H 0.4259 -0.0296 1.1340 0.047 Uiso 0.714(3) 1 calc R U P A 1
H1C H 0.4428 -0.0148 1.0602 0.047 Uiso 0.714(3) 1 calc R U P A 1
C3 C 0.3263(4) 0.3784(3) 1.12461(14) 0.0346(5) Uani 0.714(3) 1 d . . P A 1
H3A H 0.4348 0.4118 1.1282 0.041 Uiso 0.714(3) 1 calc R U P A 1
H3B H 0.2449 0.4308 1.1486 0.041 Uiso 0.714(3) 1 calc R U P A 1
C2 C 0.3248(3) 0.2251(2) 1.14644(9) 0.0310(4) Uani 0.714(3) 1 d . . P A 1
H2A H 0.3877 0.1986 1.1839 0.037 Uiso 0.714(3) 1 calc R U P A 1
H2B H 0.2126 0.1967 1.1552 0.037 Uiso 0.714(3) 1 calc R U P A 1
C4 C 0.2828(2) 0.38930(19) 1.05660(9) 0.0294(4) Uani 0.714(3) 1 d . . P A 1
H4A H 0.3377 0.4644 1.0309 0.035 Uiso 0.714(3) 1 calc R U P A 1
H4B H 0.1642 0.4048 1.0524 0.035 Uiso 0.714(3) 1 calc R U P A 1
N1 N 0.4024(2) 0.16571(16) 1.09323(7) 0.0264(3) Uani 0.714(3) 1 d . . P A 1
C5A C 0.333(4) 0.248(3) 1.0355(15) 0.0260(12) Uani 0.413(3) 1 d . . P A 2
H5A H 0.2337 0.3093 1.0256 0.031 Uiso 0.413(3) 1 calc R U P A 2
C24A C 1.117(2) 0.732(2) 0.5371(11) 0.0280(7) Uani 0.286(3) 1 d . . P A 2
H24A H 1.2120 0.6803 0.5188 0.034 Uiso 0.286(3) 1 calc R U P A 2
C23A C 1.1587(4) 0.8720(3) 0.55361(15) 0.0272(6) Uani 0.413(3) 1 d . . P A 2
H23C H 1.2770 0.8825 0.5486 0.033 Uiso 0.413(3) 1 calc R U P A 2
H23D H 1.1018 0.9479 0.5272 0.033 Uiso 0.413(3) 1 calc R U P A 2
C21A C 1.0996(7) 0.8697(4) 0.62159(18) 0.0352(8) Uani 0.413(3) 1 d . . P A 2
H21C H 0.9882 0.9127 0.6252 0.042 Uiso 0.413(3) 1 calc R U P A 2
H21D H 1.1728 0.9173 0.6444 0.042 Uiso 0.413(3) 1 calc R U P A 2
C22A C 1.1040(5) 0.7161(4) 0.64566(15) 0.0322(7) Uani 0.413(3) 1 d . . P A 2
H22C H 1.2155 0.6794 0.6554 0.039 Uiso 0.413(3) 1 calc R U P A 2
H22D H 1.0314 0.6977 0.6830 0.039 Uiso 0.413(3) 1 calc R U P A 2
N5A N 1.0465(4) 0.6577(3) 0.59366(13) 0.0292(6) Uani 0.413(3) 1 d . . P A 2
C20A C 1.0852(19) 0.5096(15) 0.5963(7) 0.045(3) Uani 0.413(3) 1 d . . P A 2
H20D H 1.0413 0.4770 0.5607 0.067 Uiso 0.413(3) 1 calc R U P A 2
H20E H 1.0370 0.4622 0.6346 0.067 Uiso 0.413(3) 1 calc R U P A 2
H20F H 1.2032 0.4907 0.5954 0.067 Uiso 0.413(3) 1 calc R U P A 2
N1A N 0.3980(6) 0.2573(4) 1.0972(2) 0.0303(9) Uani 0.286(3) 1 d . . P A 2
C4A C 0.3024(6) 0.0856(5) 1.0432(2) 0.0308(10) Uani 0.286(3) 1 d . . P A 2
H4A1 H 0.1901 0.0719 1.0332 0.037 Uiso 0.286(3) 1 calc R U P A 2
H4A2 H 0.3786 0.0382 1.0153 0.037 Uiso 0.286(3) 1 calc R U P A 2
C2A C 0.3180(7) 0.1564(6) 1.1430(2) 0.0331(10) Uani 0.286(3) 1 d . . P A 2
H2A1 H 0.2031 0.1863 1.1516 0.040 Uiso 0.286(3) 1 calc R U P A 2
H2A2 H 0.3747 0.1412 1.1823 0.040 Uiso 0.286(3) 1 calc R U P A 2
C3A C 0.3318(11) 0.0294(7) 1.1116(4) 0.0367(13) Uani 0.286(3) 1 d . . P A 2
H3A1 H 0.2488 -0.0343 1.1289 0.044 Uiso 0.286(3) 1 calc R U P A 2
H3A2 H 0.4408 -0.0183 1.1159 0.044 Uiso 0.286(3) 1 calc R U P A 2
C1A C 0.3692(14) 0.3987(8) 1.1099(4) 0.0445(19) Uani 0.286(3) 1 d . . P A 2
H1A1 H 0.4348 0.4583 1.0804 0.067 Uiso 0.286(3) 1 calc R U P A 2
H1A2 H 0.3995 0.4050 1.1521 0.067 Uiso 0.286(3) 1 calc R U P A 2
H1A3 H 0.2541 0.4276 1.1058 0.067 Uiso 0.286(3) 1 calc R U P A 2
H2 H 0.628(3) 0.222(2) 1.0465(10) 0.028(5) Uiso 1 1 d . . . . .
H8 H 0.778(3) 0.824(2) 0.4121(10) 0.030(5) Uiso 1 1 d . . . . .
H6 H 0.820(3) 0.718(3) 0.5537(11) 0.041(6) Uiso 1 1 d . . . . .
H3 H 0.681(3) 0.289(2) 0.9041(10) 0.033(5) 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
O1 C6 1.2314(17) . ?
O2 C25 1.2341(19) . ?
N3 C7 1.3679(16) . ?
N3 C8 1.4022(18) . ?
N3 H3 0.80(2) . ?
N2 C6 1.3664(18) . ?
N2 C7 1.4097(18) . ?
N2 H2 0.83(2) . ?
N7 C26 1.2880(18) . ?
N7 C27 1.4212(17) . ?
N8 C26 1.3679(17) . ?
N8 C33 1.4069(18) . ?
N8 H8 0.77(2) . ?
N6 C25 1.3645(19) . ?
N6 C26 1.4116(18) . ?
N6 H6 0.84(2) . ?
N4 C7 1.2897(17) . ?
N4 C14 1.4251(16) . ?
C8 C13 1.4001(19) . ?
C8 C9 1.4093(18) . ?
C14 C19 1.400(2) . ?
C14 C15 1.4046(18) . ?
C33 C34 1.3994(19) . ?
C33 C38 1.4055(19) . ?
C6 C5 1.50(2) . ?
C6 C5A 1.55(3) . ?
C27 C32 1.400(2) . ?
C27 C28 1.4032(18) . ?
C34 C35 1.3992(19) . ?
C34 H34 0.9500 . ?
C12 C11 1.396(2) . ?
C12 C13 1.3991(19) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C19 C18 1.3968(19) . ?
C19 H19 0.9500 . ?
C9 C10 1.389(2) . ?
C9 H9 0.9500 . ?
C38 C37 1.3898(19) . ?
C38 H38 0.9500 . ?
C36 C35 1.391(2) . ?
C36 C37 1.397(2) . ?
C36 H36 0.9500 . ?
C11 C10 1.396(2) . ?
C11 H11 0.9500 . ?
C35 H35 0.9500 . ?
C10 H10 0.9500 . ?
C18 C17 1.397(2) . ?
C18 H18 0.9500 . ?
C37 H37 0.9500 . ?
C17 C16 1.398(2) . ?
C17 H17 0.9500 . ?
C15 C16 1.3986(19) . ?
C15 H15 0.9500 . ?
C25 C24 1.509(9) . ?
C25 C24A 1.58(2) . ?
C29 C30 1.396(2) . ?
C29 C28 1.3977(19) . ?
C29 H29 0.9500 . ?
C30 C31 1.389(2) . ?
C30 H30 0.9500 . ?
C28 H28 0.9500 . ?
C16 H16 0.9500 . ?
C32 C31 1.396(2) . ?
C32 H32 0.9500 . ?
C31 H31 0.9500 . ?
C5 N1 1.42(2) . ?
C5 C4 1.60(2) . ?
C5 H5 1.0000 . ?
C24 N5 1.509(7) . ?
C24 C23 1.562(9) . ?
C24 H24 1.0000 . ?
N5 C20 1.457(3) . ?
N5 C21 1.470(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.527(10) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.549(9) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C1 N1 1.464(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C2 1.527(4) . ?
C3 C4 1.538(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C2 N1 1.469(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5A N1A 1.50(3) . ?
C5A C4A 1.63(3) . ?
C5A H5A 1.0000 . ?
C24A N5A 1.46(2) . ?
C24A C23A 1.55(2) . ?
C24A H24A 1.0000 . ?
C23A C21A 1.536(5) . ?
C23A H23C 0.9900 . ?
C23A H23D 0.9900 . ?
C21A C22A 1.537(5) . ?
C21A H21C 0.9900 . ?
C21A H21D 0.9900 . ?
C22A N5A 1.462(5) . ?
C22A H22C 0.9900 . ?
C22A H22D 0.9900 . ?
N5A C20A 1.471(15) . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 0.9800 . ?
N1A C1A 1.463(9) . ?
N1A C2A 1.479(7) . ?
C4A C3A 1.549(9) . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?
C2A C3A 1.507(11) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C1A H1A1 0.9800 . ?
C1A H1A2 0.9800 . ?
C1A H1A3 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N3 C8 129.85(12) . . ?
C7 N3 H3 112.0(16) . . ?
C8 N3 H3 118.2(16) . . ?
C6 N2 C7 130.21(11) . . ?
C6 N2 H2 114.1(15) . . ?
C7 N2 H2 115.6(15) . . ?
C26 N7 C27 117.30(12) . . ?
C26 N8 C33 130.08(12) . . ?
C26 N8 H8 114.8(16) . . ?
C33 N8 H8 115.1(16) . . ?
C25 N6 C26 129.70(13) . . ?
C25 N6 H6 109.9(17) . . ?
C26 N6 H6 120.2(17) . . ?
C7 N4 C14 116.47(11) . . ?
N4 C7 N3 124.75(12) . . ?
N4 C7 N2 121.98(12) . . ?
N3 C7 N2 113.27(11) . . ?
C13 C8 N3 125.01(12) . . ?
C13 C8 C9 119.39(12) . . ?
N3 C8 C9 115.59(12) . . ?
N7 C26 N8 125.20(12) . . ?
N7 C26 N6 121.79(12) . . ?
N8 C26 N6 113.00(12) . . ?
C19 C14 C15 119.45(12) . . ?
C19 C14 N4 120.95(11) . . ?
C15 C14 N4 119.59(12) . . ?
C34 C33 C38 119.34(12) . . ?
C34 C33 N8 124.94(12) . . ?
C38 C33 N8 115.72(12) . . ?
O1 C6 N2 125.03(13) . . ?
O1 C6 C5 124.3(8) . . ?
N2 C6 C5 110.7(8) . . ?
O1 C6 C5A 119.4(11) . . ?
N2 C6 C5A 115.6(11) . . ?
C32 C27 C28 118.95(12) . . ?
C32 C27 N7 120.67(12) . . ?
C28 C27 N7 120.35(12) . . ?
C35 C34 C33 119.11(12) . . ?
C35 C34 H34 120.4 . . ?
C33 C34 H34 120.4 . . ?
C11 C12 C13 121.19(14) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C8 119.41(12) . . ?
C12 C13 H13 120.3 . . ?
C8 C13 H13 120.3 . . ?
C18 C19 C14 120.32(12) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C10 C9 C8 120.44(13) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C37 C38 C33 120.87(13) . . ?
C37 C38 H38 119.6 . . ?
C33 C38 H38 119.6 . . ?
C35 C36 C37 119.21(13) . . ?
C35 C36 H36 120.4 . . ?
C37 C36 H36 120.4 . . ?
C12 C11 C10 119.14(13) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C36 C35 C34 121.54(13) . . ?
C36 C35 H35 119.2 . . ?
C34 C35 H35 119.2 . . ?
C9 C10 C11 120.42(13) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C19 C18 C17 120.27(14) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C38 C37 C36 119.93(13) . . ?
C38 C37 H37 120.0 . . ?
C36 C37 H37 120.0 . . ?
C18 C17 C16 119.57(13) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C16 C15 C14 119.94(13) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
O2 C25 N6 125.32(13) . . ?
O2 C25 C24 124.1(2) . . ?
N6 C25 C24 110.6(2) . . ?
O2 C25 C24A 116.1(7) . . ?
N6 C25 C24A 118.5(7) . . ?
C30 C29 C28 120.60(13) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C31 C30 C29 119.36(13) . . ?
C31 C30 H30 120.3 . . ?
C29 C30 H30 120.3 . . ?
C29 C28 C27 120.09(13) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C17 C16 C15 120.44(13) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C31 C32 C27 120.55(13) . . ?
C31 C32 H32 119.7 . . ?
C27 C32 H32 119.7 . . ?
C30 C31 C32 120.45(15) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
N1 C5 C6 115.2(13) . . ?
N1 C5 C4 105.7(14) . . ?
C6 C5 C4 108.6(13) . . ?
N1 C5 H5 109.1 . . ?
C6 C5 H5 109.1 . . ?
C4 C5 H5 109.1 . . ?
C25 C24 N5 113.4(3) . . ?
C25 C24 C23 108.6(6) . . ?
N5 C24 C23 103.0(5) . . ?
C25 C24 H24 110.5 . . ?
N5 C24 H24 110.5 . . ?
C23 C24 H24 110.5 . . ?
C20 N5 C21 114.5(2) . . ?
C20 N5 C24 113.3(4) . . ?
C21 N5 C24 108.3(4) . . ?
N5 C20 H20A 109.5 . . ?
N5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N5 C21 C22 101.6(4) . . ?
N5 C21 H21A 111.4 . . ?
C22 C21 H21A 111.4 . . ?
N5 C21 H21B 111.4 . . ?
C22 C21 H21B 111.4 . . ?
H21A C21 H21B 109.3 . . ?
C21 C22 C23 102.6(6) . . ?
C21 C22 H22A 111.3 . . ?
C23 C22 H22A 111.3 . . ?
C21 C22 H22B 111.3 . . ?
C23 C22 H22B 111.3 . . ?
H22A C22 H22B 109.2 . . ?
C22 C23 C24 105.7(5) . . ?
C22 C23 H23A 110.6 . . ?
C24 C23 H23A 110.6 . . ?
C22 C23 H23B 110.6 . . ?
C24 C23 H23B 110.6 . . ?
H23A C23 H23B 108.7 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C3 C4 102.8(2) . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
C4 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
N1 C2 C3 102.30(18) . . ?
N1 C2 H2A 111.3 . . ?
C3 C2 H2A 111.3 . . ?
N1 C2 H2B 111.3 . . ?
C3 C2 H2B 111.3 . . ?
H2A C2 H2B 109.2 . . ?
C3 C4 C5 103.0(8) . . ?
C3 C4 H4A 111.2 . . ?
C5 C4 H4A 111.2 . . ?
C3 C4 H4B 111.2 . . ?
C5 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
C5 N1 C1 113.2(9) . . ?
C5 N1 C2 109.0(9) . . ?
C1 N1 C2 113.75(19) . . ?
N1A C5A C6 107.5(18) . . ?
N1A C5A C4A 100.3(17) . . ?
C6 C5A C4A 104.8(18) . . ?
N1A C5A H5A 114.3 . . ?
C6 C5A H5A 114.3 . . ?
C4A C5A H5A 114.3 . . ?
N5A C24A C23A 106.4(15) . . ?
N5A C24A C25 105.5(11) . . ?
C23A C24A C25 104.7(14) . . ?
N5A C24A H24A 113.2 . . ?
C23A C24A H24A 113.2 . . ?
C25 C24A H24A 113.2 . . ?
C21A C23A C24A 104.3(8) . . ?
C21A C23A H23C 110.9 . . ?
C24A C23A H23C 110.9 . . ?
C21A C23A H23D 110.9 . . ?
C24A C23A H23D 110.9 . . ?
H23C C23A H23D 108.9 . . ?
C23A C21A C22A 103.0(3) . . ?
C23A C21A H21C 111.2 . . ?
C22A C21A H21C 111.2 . . ?
C23A C21A H21D 111.2 . . ?
C22A C21A H21D 111.2 . . ?
H21C C21A H21D 109.1 . . ?
N5A C22A C21A 102.6(3) . . ?
N5A C22A H22C 111.2 . . ?
C21A C22A H22C 111.2 . . ?
N5A C22A H22D 111.2 . . ?
C21A C22A H22D 111.2 . . ?
H22C C22A H22D 109.2 . . ?
C22A N5A C24A 107.2(10) . . ?
C22A N5A C20A 113.8(6) . . ?
C24A N5A C20A 111.1(11) . . ?
N5A C20A H20D 109.5 . . ?
N5A C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
N5A C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C1A N1A C2A 114.1(5) . . ?
C1A N1A C5A 108.3(12) . . ?
C2A N1A C5A 107.4(13) . . ?
C3A C4A C5A 106.2(12) . . ?
C3A C4A H4A1 110.5 . . ?
C5A C4A H4A1 110.5 . . ?
C3A C4A H4A2 110.5 . . ?
C5A C4A H4A2 110.5 . . ?
H4A1 C4A H4A2 108.7 . . ?
N1A C2A C3A 102.9(5) . . ?
N1A C2A H2A1 111.2 . . ?
C3A C2A H2A1 111.2 . . ?
N1A C2A H2A2 111.2 . . ?
C3A C2A H2A2 111.2 . . ?
H2A1 C2A H2A2 109.1 . . ?
C2A C3A C4A 103.3(5) . . ?
C2A C3A H3A1 111.1 . . ?
C4A C3A H3A1 111.1 . . ?
C2A C3A H3A2 111.1 . . ?
C4A C3A H3A2 111.1 . . ?
H3A1 C3A H3A2 109.1 . . ?
N1A C1A H1A1 109.5 . . ?
N1A C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 109.5 . . ?
N1A C1A H1A3 109.5 . . ?
H1A1 C1A H1A3 109.5 . . ?
H1A2 C1A H1A3 109.5 . . ?

_refine_diff_density_max         0.631
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_2016ncs0748
_database_code_depnum_ccdc_archive 'CCDC 1952632'
loop_
_audit_author_name
_audit_author_address
'Jeppe Christensen '
;national crystallography service (southampton) and diamond light source (didcot)
United Kingdom
;
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H30 N4 O'
_chemical_formula_sum            'C24 H30 N4 O'
_chemical_formula_weight         390.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.3748(2)
_cell_length_b                   9.6012(2)
_cell_length_c                   12.5616(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.848(2)
_cell_angle_gamma                90
_cell_volume                     1092.91(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3446
_cell_measurement_theta_max      30.26
_cell_measurement_theta_min      1.62

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.095
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.022
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_T_min  0.996641639337
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CCP4 7.0.025: AIMLESS, version 0.5.29 : 17/10/16
Scaling & analysis of unmerged intensities, 
absorption correction using spherical harmonics
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_dtime           0.004
_diffrn_detector_type            'Dectris, PILATUS 2M'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_details 
;
custom build fixed Chi diffractometer, Chi=54
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_radiation_collimation    'focusing mirrors and 0.0100 mm pinhole'
_diffrn_radiation_monochromator  'Si 111, double crystal monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_source_type              'DLS beamline I19, undulator'
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_wavelength_determination estimated
_diffrn_radiation_wavelength_details 'Zr absorption edge'

_diffrn_reflns_number            11102
_diffrn_reflns_av_unetI/netI     0.0901
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.178
_diffrn_reflns_theta_max         26.569
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             4942
_reflns_number_gt                4120
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_max     0.963
_reflns_Friedel_fraction_full    0.966

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'GDA http://www.opengda.org/OpenGDA.html'
_computing_cell_refinement       
'XIA2 0.4.0.438-g4431aaa, Winter, G. (2010) J. Appl. Cryst. 43'
_computing_data_reduction        
'XIA2 0.4.0.438-g4431aaa, Winter, G. (2010) J. Appl. Cryst. 43'
_computing_structure_solution    'SHELXT Acta Cryst. (2015). A71, 3-8'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0456P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1474 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4942
_refine_ls_number_parameters     270
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1321
_refine_ls_wR_factor_gt          0.1233
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4894(2) 0.4589(2) 0.43778(17) 0.0401(5) Uani 1 1 d . . . . .
N2 N 0.6204(2) 0.5760(2) 0.59090(18) 0.0281(5) Uani 1 1 d . . . . .
N1 N 0.4304(2) 0.5169(2) 0.70805(19) 0.0270(5) Uani 1 1 d . . . . .
N4 N 0.8563(2) 0.6789(2) 0.62821(18) 0.0309(5) Uani 1 1 d . . . . .
N3 N 0.7413(3) 0.5957(2) 0.45275(19) 0.0312(5) Uani 1 1 d . . . . .
C12 C 0.7469(3) 0.6219(3) 0.5608(2) 0.0271(5) Uani 1 1 d . . . . .
C11 C 0.5024(3) 0.5027(3) 0.5314(2) 0.0299(6) Uani 1 1 d . . . . .
C10 C 0.3803(3) 0.4830(3) 0.5900(2) 0.0280(5) Uani 1 1 d . . . . .
H10 H 0.3433 0.3849 0.5805 0.034 Uiso 1 1 calc R U . . .
C19 C 0.8496(3) 0.6998(3) 0.7391(2) 0.0287(6) Uani 1 1 d . . . . .
C13 C 0.8425(3) 0.6373(3) 0.3937(2) 0.0294(6) Uani 1 1 d . . . . .
C18 C 0.9318(3) 0.7547(3) 0.4198(2) 0.0311(6) Uani 1 1 d . . . . .
H18 H 0.9322 0.8072 0.4840 0.037 Uiso 1 1 calc R U . . .
C20 C 0.7631(3) 0.8036(3) 0.7672(2) 0.0344(6) Uani 1 1 d . . . . .
H20 H 0.7051 0.8619 0.7116 0.041 Uiso 1 1 calc R U . . .
C8 C 0.2682(3) 0.6973(3) 0.6287(2) 0.0358(6) Uani 1 1 d . . . . .
H8A H 0.3405 0.7693 0.6211 0.043 Uiso 1 1 calc R U . . .
H8B H 0.1723 0.7425 0.6258 0.043 Uiso 1 1 calc R U . . .
C9 C 0.2523(3) 0.5855(3) 0.5404(2) 0.0356(6) Uani 1 1 d . . . . .
H9A H 0.2630 0.6257 0.4703 0.043 Uiso 1 1 calc R U . . .
H9B H 0.1554 0.5384 0.5271 0.043 Uiso 1 1 calc R U . . .
C22 C 0.8452(3) 0.7393(3) 0.9585(2) 0.0354(6) Uani 1 1 d . . . . .
H22 H 0.8427 0.7523 1.0330 0.042 Uiso 1 1 calc R U . . .
C7 C 0.3229(3) 0.6147(3) 0.7340(2) 0.0347(6) Uani 1 1 d . . . . .
H7A H 0.3707 0.6763 0.7961 0.042 Uiso 1 1 calc R U . . .
H7B H 0.2409 0.5640 0.7531 0.042 Uiso 1 1 calc R U . . .
C23 C 0.9331(3) 0.6368(3) 0.9309(2) 0.0364(6) Uani 1 1 d . . . . .
H23 H 0.9923 0.5798 0.9869 0.044 Uiso 1 1 calc R U . . .
C24 C 0.9355(3) 0.6167(3) 0.8222(2) 0.0344(6) Uani 1 1 d . . . . .
H24 H 0.9961 0.5458 0.8042 0.041 Uiso 1 1 calc R U . . .
C17 C 1.0203(3) 0.7949(3) 0.3519(2) 0.0378(7) Uani 1 1 d . . . . .
H17 H 1.0799 0.8759 0.3695 0.045 Uiso 1 1 calc R U . . .
C6 C 0.4643(3) 0.3954(3) 0.7819(2) 0.0309(6) Uani 1 1 d . . . . .
H6 H 0.3716 0.3409 0.7755 0.037 Uiso 1 1 calc R U . . .
C14 C 0.8460(4) 0.5597(3) 0.3002(2) 0.0378(6) Uani 1 1 d . . . . .
H14 H 0.7858 0.4793 0.2816 0.045 Uiso 1 1 calc R U . . .
C5 C 0.5782(3) 0.3012(3) 0.7500(3) 0.0361(6) Uani 1 1 d . . . . .
H5A H 0.5373 0.2658 0.6743 0.043 Uiso 1 1 calc R U . . .
H5B H 0.6677 0.3563 0.7505 0.043 Uiso 1 1 calc R U . . .
C21 C 0.7610(3) 0.8225(3) 0.8762(2) 0.0377(6) Uani 1 1 d . . . . .
H21 H 0.7009 0.8935 0.8946 0.045 Uiso 1 1 calc R U . . .
C1 C 0.5218(4) 0.4442(3) 0.9004(2) 0.0398(7) Uani 1 1 d . . . . .
H1A H 0.4438 0.4983 0.9220 0.048 Uiso 1 1 calc R U . . .
H1B H 0.6074 0.5065 0.9057 0.048 Uiso 1 1 calc R U . . .
C16 C 1.0226(3) 0.7185(4) 0.2591(3) 0.0435(8) Uani 1 1 d . . . . .
H16 H 1.0824 0.7473 0.2125 0.052 Uiso 1 1 calc R U . . .
C15 C 0.9372(4) 0.6001(3) 0.2349(2) 0.0430(7) Uani 1 1 d . . . . .
H15 H 0.9410 0.5456 0.1726 0.052 Uiso 1 1 calc R U . . .
C4 C 0.6203(4) 0.1785(3) 0.8287(3) 0.0460(8) Uani 1 1 d . . . . .
H4A H 0.5325 0.1194 0.8242 0.055 Uiso 1 1 calc R U . . .
H4B H 0.6959 0.1213 0.8068 0.055 Uiso 1 1 calc R U . . .
C3 C 0.6805(4) 0.2286(4) 0.9464(3) 0.0509(9) Uani 1 1 d . . . . .
H3A H 0.7731 0.2812 0.9524 0.061 Uiso 1 1 calc R U . . .
H3B H 0.7032 0.1474 0.9965 0.061 Uiso 1 1 calc R U . . .
C2 C 0.5684(4) 0.3215(4) 0.9804(3) 0.0513(9) Uani 1 1 d . . . . .
H2A H 0.6116 0.3579 1.0555 0.062 Uiso 1 1 calc R U . . .
H2B H 0.4802 0.2658 0.9823 0.062 Uiso 1 1 calc R U . . .
H25 H 0.611(3) 0.600(3) 0.653(3) 0.027(7) Uiso 1 1 d . . . . .
H26 H 0.668(4) 0.549(4) 0.415(3) 0.046(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
O1 C11 1.226(3) . ?
N2 C11 1.362(3) . ?
N2 C12 1.404(3) . ?
N2 H25 0.84(3) . ?
N1 C10 1.473(3) . ?
N1 C7 1.473(3) . ?
N1 C6 1.474(3) . ?
N4 C12 1.274(3) . ?
N4 C19 1.424(3) . ?
N3 C12 1.369(3) . ?
N3 C13 1.404(3) . ?
N3 H26 0.85(4) . ?
C11 C10 1.522(4) . ?
C10 C9 1.554(4) . ?
C10 H10 1.0000 . ?
C19 C20 1.387(4) . ?
C19 C24 1.394(4) . ?
C13 C18 1.392(4) . ?
C13 C14 1.398(4) . ?
C18 C17 1.388(4) . ?
C18 H18 0.9500 . ?
C20 C21 1.387(4) . ?
C20 H20 0.9500 . ?
C8 C7 1.515(4) . ?
C8 C9 1.524(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C22 C21 1.383(4) . ?
C22 C23 1.383(4) . ?
C22 H22 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C23 C24 1.384(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C17 C16 1.382(5) . ?
C17 H17 0.9500 . ?
C6 C1 1.522(4) . ?
C6 C5 1.528(4) . ?
C6 H6 1.0000 . ?
C14 C15 1.383(4) . ?
C14 H14 0.9500 . ?
C5 C4 1.524(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C21 H21 0.9500 . ?
C1 C2 1.537(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C16 C15 1.379(5) . ?
C16 H16 0.9500 . ?
C15 H15 0.9500 . ?
C4 C3 1.519(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C3 C2 1.520(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N2 C12 129.6(2) . . ?
C11 N2 H25 113(2) . . ?
C12 N2 H25 117(2) . . ?
C10 N1 C7 107.7(2) . . ?
C10 N1 C6 114.8(2) . . ?
C7 N1 C6 114.5(2) . . ?
C12 N4 C19 118.7(2) . . ?
C12 N3 C13 127.8(2) . . ?
C12 N3 H26 118(2) . . ?
C13 N3 H26 114(2) . . ?
N4 C12 N3 123.9(2) . . ?
N4 C12 N2 123.2(2) . . ?
N3 C12 N2 112.9(2) . . ?
O1 C11 N2 124.8(2) . . ?
O1 C11 C10 121.3(2) . . ?
N2 C11 C10 113.9(2) . . ?
N1 C10 C11 112.0(2) . . ?
N1 C10 C9 106.1(2) . . ?
C11 C10 C9 109.1(2) . . ?
N1 C10 H10 109.9 . . ?
C11 C10 H10 109.9 . . ?
C9 C10 H10 109.9 . . ?
C20 C19 C24 118.9(3) . . ?
C20 C19 N4 121.7(2) . . ?
C24 C19 N4 119.4(2) . . ?
C18 C13 C14 119.2(3) . . ?
C18 C13 N3 123.6(3) . . ?
C14 C13 N3 117.1(3) . . ?
C17 C18 C13 119.9(3) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
C21 C20 C19 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C7 C8 C9 102.4(2) . . ?
C7 C8 H8A 111.3 . . ?
C9 C8 H8A 111.3 . . ?
C7 C8 H8B 111.3 . . ?
C9 C8 H8B 111.3 . . ?
H8A C8 H8B 109.2 . . ?
C8 C9 C10 103.5(2) . . ?
C8 C9 H9A 111.1 . . ?
C10 C9 H9A 111.1 . . ?
C8 C9 H9B 111.1 . . ?
C10 C9 H9B 111.1 . . ?
H9A C9 H9B 109.0 . . ?
C21 C22 C23 119.1(3) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
N1 C7 C8 103.8(2) . . ?
N1 C7 H7A 111.0 . . ?
C8 C7 H7A 111.0 . . ?
N1 C7 H7B 111.0 . . ?
C8 C7 H7B 111.0 . . ?
H7A C7 H7B 109.0 . . ?
C22 C23 C24 120.5(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C19 120.4(3) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?
C16 C17 C18 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
N1 C6 C1 109.7(2) . . ?
N1 C6 C5 110.9(2) . . ?
C1 C6 C5 110.0(2) . . ?
N1 C6 H6 108.7 . . ?
C1 C6 H6 108.7 . . ?
C5 C6 H6 108.7 . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C4 C5 C6 111.7(2) . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
C22 C21 C20 120.8(3) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C6 C1 C2 111.9(3) . . ?
C6 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
C6 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C15 C16 C17 119.3(3) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C15 C14 120.8(3) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C3 C4 C5 110.9(3) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.0 . . ?
C4 C3 C2 110.4(3) . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C3 C2 C1 111.5(3) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.042

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

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1952631'
loop_
_audit_author_name
_audit_author_address
'Jeppe Christensen '
;national crystallography service (southampton) and diamond light source (didcot)
United Kingdom
;
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H26 N4 O'
_chemical_formula_sum            'C21 H26 N4 O'
_chemical_formula_weight         350.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0010 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.600(3)
_cell_length_b                   9.896(4)
_cell_length_c                   11.880(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.38(2)
_cell_angle_gamma                90
_cell_volume                     969.9(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3884
_cell_measurement_theta_min      1.73395988227
_cell_measurement_theta_max      30.6454328828

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.997
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_T_min  0.998
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CCP4 7.0.017: AIMLESS, version 0.5.27 : 18/05/16
Scaling & analysis of unmerged intensities, 
absorption correction using spherical harmonics
Run via XIA2 0.4.0.438-g4431aaa, 
DIALS 1.dev.489-gd9b5119, DIALS/i19 0.86-g06248aa
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_dtime           0.004
_diffrn_detector_type            'Dectris, PILATUS 2M'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_details 
;
custom build fixed Chi diffractometer, Chi=54
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_radiation_collimation    'focusing mirrors and 0.0100 mm pinhole'
_diffrn_radiation_monochromator  'Si 111, double crystal monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_source_type              'DLS beamline I19, undulator'
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_wavelength_determination estimated
_diffrn_radiation_wavelength_details 'Zr absorption edge'
_diffrn_reflns_number            17850
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_av_R_equivalents  0.0907
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.732
_diffrn_reflns_theta_max         26.573
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4416
_reflns_number_gt                4208
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.882
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.995

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'GDA http://www.opengda.org/OpenGDA.html'
_computing_cell_refinement       
'XIA2 0.4.0.438-g4431aaa, Winter, G. (2010) J. Appl. Cryst. 43'
_computing_data_reduction        
'XIA2 0.4.0.438-g4431aaa, Winter, G. (2010) J. Appl. Cryst. 43'
_computing_structure_solution    'SHELXT Acta Cryst. (2015). A71, 3-8'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0672P)²+0.0628P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1828 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(6)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4416
_refine_ls_number_parameters     245
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1311
_refine_ls_wR_factor_gt          0.1291
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0652(2) 0.6239(2) 0.19215(18) 0.0429(5) Uani 1 1 d . . . . .
N1 N 0.2774(2) 0.4774(2) 0.26537(16) 0.0273(4) Uani 1 1 d . . . . .
N2 N 0.3733(2) 0.66446(19) 0.18801(17) 0.0292(4) Uani 1 1 d . . . . .
N3 N 0.5528(2) 0.4905(2) 0.27163(17) 0.0296(4) Uani 1 1 d . . . . .
N4 N 0.0831(2) 0.2800(2) 0.29964(17) 0.0318(4) Uani 1 1 d . . . . .
C9 C 0.4109(2) 0.5429(2) 0.24272(17) 0.0261(4) Uani 1 1 d . . . . .
C10 C 0.4744(3) 0.7537(2) 0.14864(18) 0.0282(4) Uani 1 1 d . . . . .
C8 C 0.1187(3) 0.5168(2) 0.23877(19) 0.0322(5) Uani 1 1 d . . . . .
C16 C 0.5731(2) 0.3626(2) 0.32800(19) 0.0288(4) Uani 1 1 d . . . . .
C15 C 0.6435(3) 0.7444(2) 0.1800(2) 0.0311(4) Uani 1 1 d . . . . .
H15 H 0.6969 0.6764 0.2302 0.037 Uiso 1 1 calc R U . . .
C21 C 0.6148(3) 0.3559(2) 0.4504(2) 0.0325(5) Uani 1 1 d . . . . .
H21 H 0.6287 0.4350 0.4944 0.039 Uiso 1 1 calc R U . . .
C11 C 0.3974(3) 0.8574(2) 0.07355(19) 0.0334(5) Uani 1 1 d . . . . .
H11 H 0.2850 0.8639 0.0522 0.040 Uiso 1 1 calc R U . . .
C20 C 0.6354(3) 0.2313(3) 0.5067(2) 0.0375(5) Uani 1 1 d . . . . .
H20 H 0.6616 0.2273 0.5881 0.045 Uiso 1 1 calc R U . . .
C17 C 0.5583(3) 0.2427(2) 0.2634(2) 0.0328(5) Uani 1 1 d . . . . .
H17 H 0.5340 0.2460 0.1820 0.039 Uiso 1 1 calc R U . . .
C19 C 0.6173(3) 0.1129(3) 0.4420(2) 0.0362(5) Uani 1 1 d . . . . .
H19 H 0.6301 0.0297 0.4799 0.043 Uiso 1 1 calc R U . . .
C14 C 0.7311(3) 0.8386(2) 0.1350(2) 0.0365(5) Uani 1 1 d . . . . .
H14 H 0.8435 0.8323 0.1555 0.044 Uiso 1 1 calc R U . . .
C12 C 0.4865(3) 0.9507(3) 0.0306(2) 0.0382(5) Uani 1 1 d . . . . .
H12 H 0.4340 1.0200 -0.0184 0.046 Uiso 1 1 calc R U . . .
C13 C 0.6549(3) 0.9405(3) 0.0609(2) 0.0388(5) Uani 1 1 d . . . . .
H13 H 0.7152 1.0019 0.0313 0.047 Uiso 1 1 calc R U . . .
C6 C -0.0077(3) 0.4645(3) 0.4001(2) 0.0367(5) Uani 1 1 d . . . . .
H6A H 0.0507 0.5481 0.4248 0.044 Uiso 1 1 calc R U . . .
H6B H -0.1211 0.4783 0.3954 0.044 Uiso 1 1 calc R U . . .
C18 C 0.5800(3) 0.1187(2) 0.3206(2) 0.0357(5) Uani 1 1 d . . . . .
H18 H 0.5695 0.0392 0.2773 0.043 Uiso 1 1 calc R U . . .
C4 C 0.0477(3) 0.2276(3) 0.4063(2) 0.0380(5) Uani 1 1 d . . . . .
H4A H 0.1246 0.1580 0.4432 0.046 Uiso 1 1 calc R U . . .
H4B H -0.0610 0.1906 0.3879 0.046 Uiso 1 1 calc R U . . .
C7 C 0.0116(2) 0.4170(3) 0.2797(2) 0.0327(5) Uani 1 1 d . . . . .
H7 H -0.0951 0.4126 0.2219 0.039 Uiso 1 1 calc R U . . .
C5 C 0.0640(3) 0.3500(3) 0.4847(2) 0.0421(6) Uani 1 1 d . . . . .
H5A H 0.1767 0.3675 0.5256 0.051 Uiso 1 1 calc R U . . .
H5B H 0.0040 0.3378 0.5420 0.051 Uiso 1 1 calc R U . . .
C3 C 0.0275(3) 0.1892(3) 0.1977(2) 0.0412(6) Uani 1 1 d . . . . .
H3 H -0.0905 0.1800 0.1788 0.049 Uiso 1 1 calc R U . . .
C1 C 0.0702(4) 0.2457(4) 0.0904(2) 0.0506(7) Uani 1 1 d . . . . .
H1A H 0.0249 0.3346 0.0733 0.076 Uiso 1 1 calc R U . . .
H1B H 0.0267 0.1876 0.0243 0.076 Uiso 1 1 calc R U . . .
H1C H 0.1859 0.2505 0.1063 0.076 Uiso 1 1 calc R U . . .
C2 C 0.1041(4) 0.0497(3) 0.2266(3) 0.0548(8) Uani 1 1 d . . . . .
H2A H 0.2197 0.0588 0.2557 0.082 Uiso 1 1 calc R U . . .
H2B H 0.0775 -0.0050 0.1571 0.082 Uiso 1 1 calc R U . . .
H2C H 0.0632 0.0075 0.2853 0.082 Uiso 1 1 calc R U . . .
H1 H 0.296(3) 0.400(3) 0.290(2) 0.028(6) Uiso 1 1 d . . . . .
H2 H 0.285(4) 0.690(4) 0.179(3) 0.041(8) 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
O1 C8 1.224(3) . ?
N1 C8 1.368(3) . ?
N1 C9 1.409(3) . ?
N2 C9 1.362(3) . ?
N2 C10 1.409(3) . ?
N3 C9 1.280(3) . ?
N3 C16 1.420(3) . ?
N4 C3 1.475(3) . ?
N4 C4 1.478(3) . ?
N4 C7 1.480(3) . ?
C10 C15 1.399(3) . ?
C10 C11 1.398(3) . ?
C8 C7 1.521(3) . ?
C16 C21 1.398(3) . ?
C16 C17 1.400(3) . ?
C15 C14 1.396(3) . ?
C21 C20 1.390(3) . ?
C11 C12 1.385(3) . ?
C20 C19 1.386(4) . ?
C17 C18 1.389(3) . ?
C19 C18 1.388(4) . ?
C14 C13 1.377(4) . ?
C12 C13 1.393(4) . ?
C6 C5 1.525(4) . ?
C6 C7 1.557(3) . ?
C4 C5 1.510(4) . ?
C3 C2 1.527(4) . ?
C3 C1 1.529(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C9 129.7(2) . . ?
C9 N2 C10 128.78(18) . . ?
C9 N3 C16 117.92(18) . . ?
C3 N4 C4 113.12(18) . . ?
C3 N4 C7 113.77(19) . . ?
C4 N4 C7 106.36(19) . . ?
N3 C9 N2 124.45(19) . . ?
N3 C9 N1 121.9(2) . . ?
N2 C9 N1 113.62(18) . . ?
C15 C10 C11 119.2(2) . . ?
C15 C10 N2 124.2(2) . . ?
C11 C10 N2 116.53(19) . . ?
O1 C8 N1 125.1(2) . . ?
O1 C8 C7 121.5(2) . . ?
N1 C8 C7 113.3(2) . . ?
C21 C16 C17 119.2(2) . . ?
C21 C16 N3 119.6(2) . . ?
C17 C16 N3 121.13(19) . . ?
C14 C15 C10 119.1(2) . . ?
C20 C21 C16 120.2(2) . . ?
C12 C11 C10 120.8(2) . . ?
C19 C20 C21 120.3(2) . . ?
C18 C17 C16 120.1(2) . . ?
C20 C19 C18 119.9(2) . . ?
C13 C14 C15 121.5(2) . . ?
C11 C12 C13 119.9(2) . . ?
C14 C13 C12 119.4(2) . . ?
C5 C6 C7 104.7(2) . . ?
C19 C18 C17 120.3(2) . . ?
N4 C4 C5 104.00(19) . . ?
N4 C7 C8 112.60(18) . . ?
N4 C7 C6 106.06(19) . . ?
C8 C7 C6 109.21(19) . . ?
C4 C5 C6 103.8(2) . . ?
N4 C3 C2 110.3(2) . . ?
N4 C3 C1 111.3(2) . . ?
C2 C3 C1 109.2(2) . . ?

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.052

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

data_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1952637'
loop_
_audit_author_name
_audit_author_address
'Jeppe Christensen '
;national crystallography service (southampton) and diamond light source (didcot)
United Kingdom
;
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H16 N4 O1'
_chemical_formula_sum            'C13 H16 N4 O'
_chemical_formula_weight         244.30

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.8292(2)
_cell_length_b                   12.6358(4)
_cell_length_c                   10.1195(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.835(2)
_cell_angle_gamma                90
_cell_volume                     1252.37(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5434
_cell_measurement_theta_min      4.4920
_cell_measurement_theta_max      69.3610

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.045
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.008
_exptl_absorpt_coefficient_mu    0.695
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_T_min  0.87199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measurement_details      
;
Data collection strategy using shutter-less operation of detector. 

List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -180.00   0.00   0.50    2.00    --  -90.00  54.00   0.00  360
  2  ω   -180.00   0.00   0.50    2.00    --  -90.00  54.00 120.00  360
  3  ω   -180.00   0.00   0.50    2.00    --  -90.00  54.00 240.00  360
  4  ω   -124.00  55.00   0.50    0.50    --  -35.00  54.00 240.00  358
  5  ω   -124.00  55.00   0.50    0.50    --  -35.00  54.00 120.00  358
  6  ω   -124.00  55.00   0.50    0.50    --  -35.00  54.00   0.00  358
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC11 quarter χ goniometer'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_radiation_collimation    'Varimax focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'Rotating anode'
_diffrn_source_type              'Rigaku 007 HF'
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_source_current           30.0
_diffrn_source_target            Cu
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_reflns_number            11865
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.515
_diffrn_reflns_theta_max         70.486
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_point_group_measured_fraction_full 0.901
_reflns_number_total             4184
_reflns_number_gt                3802
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_max     0.767
_reflns_Friedel_fraction_full    0.806

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0608P)²+0.3387P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1448 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(19)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4184
_refine_ls_number_parameters     343
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1207
_refine_ls_wR_factor_gt          0.1169
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5652(2) 0.4608(2) 0.7731(2) 0.0401(6) Uani 1 1 d . . . . .
N4 N 0.8204(3) 0.5156(3) 1.1123(2) 0.0313(6) Uani 1 1 d . . . . .
N6 N 0.6396(3) 0.5714(3) 0.5132(3) 0.0339(7) Uani 1 1 d . . . . .
N3 N 0.8190(3) 0.5202(3) 0.8898(3) 0.0308(6) Uani 1 1 d . . . . .
N7 N 0.8173(3) 0.4909(2) 0.3963(3) 0.0302(6) Uani 1 1 d . . . . .
N8 N 0.8231(3) 0.4735(2) 0.6171(2) 0.0314(6) Uani 1 1 d . . . . .
N1 N 0.4248(3) 0.3050(3) 1.0296(3) 0.0372(7) Uani 1 1 d . . . . .
O2 O 0.6075(3) 0.6211(3) 0.2978(2) 0.0595(9) Uani 1 1 d . . . . .
N2 N 0.6404(3) 0.4267(3) 0.9886(3) 0.0321(7) Uani 1 1 d . . . . .
C8 C 0.9296(3) 0.5798(3) 0.9381(3) 0.0297(7) Uani 1 1 d . . . . .
C7 C 0.7585(3) 0.4863(3) 0.9987(3) 0.0295(7) Uani 1 1 d . . . . .
C13 C 0.9296(3) 0.5765(3) 1.0772(3) 0.0312(7) Uani 1 1 d . . . . .
C12 C 1.0271(4) 0.6332(3) 1.1559(3) 0.0368(8) Uani 1 1 d . . . . .
H12 H 1.0298 0.6306 1.2499 0.044 Uiso 1 1 calc R U . . .
C22 C 1.0196(3) 0.3726(3) 0.3594(3) 0.0361(8) Uani 1 1 d . . . . .
H22 H 1.0183 0.3803 0.2659 0.043 Uiso 1 1 calc R U . . .
C6 C 0.5473(3) 0.4218(3) 0.8800(3) 0.0319(7) Uani 1 1 d . . . . .
C9 C 1.0238(3) 0.6394(3) 0.8744(3) 0.0351(8) Uani 1 1 d . . . . .
H9 H 1.0232 0.6407 0.7805 0.042 Uiso 1 1 calc R U . . .
C20 C 0.7588(3) 0.5145(3) 0.5092(3) 0.0304(7) Uani 1 1 d . . . . .
N5 N 0.3866(3) 0.6326(3) 0.5599(3) 0.0541(10) Uani 1 1 d . . . . .
C21 C 0.9268(3) 0.4264(3) 0.4326(3) 0.0313(8) Uani 1 1 d . . . . .
C11 C 1.1204(4) 0.6938(3) 1.0930(4) 0.0405(9) Uani 1 1 d . . . . .
H11 H 1.1869 0.7340 1.1448 0.049 Uiso 1 1 calc R U . . .
C10 C 1.1180(4) 0.6965(3) 0.9542(3) 0.0393(9) Uani 1 1 d . . . . .
H10 H 1.1830 0.7388 0.9141 0.047 Uiso 1 1 calc R U . . .
C26 C 0.9300(3) 0.4156(3) 0.5712(3) 0.0302(7) Uani 1 1 d . . . . .
C23 C 1.1135(3) 0.3075(3) 0.4296(4) 0.0387(8) Uani 1 1 d . . . . .
H23 H 1.1772 0.2688 0.3831 0.046 Uiso 1 1 calc R U . . .
C5 C 0.4149(3) 0.3660(3) 0.9051(3) 0.0368(8) Uani 1 1 d . . . . .
H5 H 0.3882 0.3174 0.8293 0.044 Uiso 1 1 calc R U . . .
C24 C 1.1166(4) 0.2975(3) 0.5672(4) 0.0391(9) Uani 1 1 d . . . . .
H24 H 1.1826 0.2525 0.6122 0.047 Uiso 1 1 calc R U . . .
C25 C 1.0257(3) 0.3515(3) 0.6394(3) 0.0343(8) Uani 1 1 d . . . . .
H25 H 1.0289 0.3448 0.7332 0.041 Uiso 1 1 calc R U . . .
C1 C 0.4723(4) 0.1977(3) 1.0141(4) 0.0470(10) Uani 1 1 d . . . . .
H1A H 0.4094 0.1602 0.9499 0.070 Uiso 1 1 calc R U . . .
H1B H 0.4760 0.1612 1.0998 0.070 Uiso 1 1 calc R U . . .
H1C H 0.5636 0.1990 0.9821 0.070 Uiso 1 1 calc R U . . .
C19 C 0.5677(4) 0.6191(4) 0.4090(3) 0.0395(8) Uani 1 1 d . . . . .
C4 C 0.3004(4) 0.4470(4) 0.9185(4) 0.0504(10) Uani 1 1 d . . . . .
H4A H 0.3369 0.5201 0.9199 0.061 Uiso 1 1 calc R U . . .
H4B H 0.2289 0.4404 0.8439 0.061 Uiso 1 1 calc R U . . .
C18 C 0.4398(4) 0.6753(4) 0.4426(4) 0.0445(9) Uani 1 1 d . . . . .
H18 H 0.3688 0.6721 0.3659 0.053 Uiso 1 1 calc R U . . .
C15 C 0.3363(6) 0.7186(5) 0.6356(5) 0.0702(16) Uani 1 1 d . . . . .
H15A H 0.3281 0.6978 0.7290 0.084 Uiso 1 1 calc R U . . .
H15B H 0.2468 0.7443 0.5962 0.084 Uiso 1 1 calc R U . . .
C2 C 0.2868(4) 0.3096(5) 1.0745(5) 0.0627(13) Uani 1 1 d . . . . .
H2A H 0.2881 0.2922 1.1700 0.075 Uiso 1 1 calc R U . . .
H2B H 0.2249 0.2598 1.0235 0.075 Uiso 1 1 calc R U . . .
C17 C 0.4717(5) 0.7950(4) 0.4828(5) 0.0569(11) Uani 1 1 d . . . . .
H17A H 0.5673 0.8133 0.4685 0.068 Uiso 1 1 calc R U . . .
H17B H 0.4099 0.8437 0.4299 0.068 Uiso 1 1 calc R U . . .
C16 C 0.4488(5) 0.8018(5) 0.6247(5) 0.0679(13) Uani 1 1 d . . . . .
H16A H 0.4174 0.8733 0.6485 0.081 Uiso 1 1 calc R U . . .
H16B H 0.5324 0.7836 0.6817 0.081 Uiso 1 1 calc R U . . .
C3 C 0.2430(6) 0.4204(6) 1.0497(6) 0.091(2) Uani 1 1 d . . . . .
H3A H 0.2813 0.4677 1.1214 0.109 Uiso 1 1 calc R U . . .
H3B H 0.1422 0.4263 1.0424 0.109 Uiso 1 1 calc R U . . .
C14 C 0.2834(6) 0.5506(5) 0.5311(7) 0.087(2) Uani 1 1 d . . . . .
H14A H 0.1973 0.5835 0.4968 0.131 Uiso 1 1 calc R U . . .
H14B H 0.2694 0.5115 0.6125 0.131 Uiso 1 1 calc R U . . .
H14C H 0.3143 0.5017 0.4646 0.131 Uiso 1 1 calc R U . . .
H1 H 0.797(4) 0.507(3) 0.807(4) 0.031(9) Uiso 1 1 d . . . . .
H2 H 0.790(4) 0.512(4) 0.320(5) 0.052(13) Uiso 1 1 d . . . . .
H3 H 0.608(4) 0.563(3) 0.585(4) 0.034(10) Uiso 1 1 d . . . . .
H4 H 0.611(5) 0.403(4) 1.048(4) 0.049(13) 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
O1 C6 1.215(4) . ?
N4 C7 1.308(4) . ?
N4 C13 1.391(4) . ?
N6 C19 1.359(5) . ?
N6 C20 1.378(4) . ?
N6 H3 0.82(4) . ?
N3 C7 1.364(4) . ?
N3 C8 1.378(5) . ?
N3 H1 0.86(4) . ?
N7 C20 1.355(4) . ?
N7 C21 1.376(4) . ?
N7 H2 0.84(5) . ?
N8 C20 1.321(4) . ?
N8 C26 1.392(4) . ?
N1 C1 1.446(5) . ?
N1 C2 1.468(5) . ?
N1 C5 1.473(5) . ?
O2 C19 1.223(4) . ?
N2 C6 1.371(4) . ?
N2 C7 1.381(5) . ?
N2 H4 0.76(4) . ?
C8 C9 1.393(5) . ?
C8 C13 1.408(4) . ?
C13 C12 1.392(5) . ?
C12 C11 1.389(5) . ?
C12 H12 0.9500 . ?
C22 C23 1.388(5) . ?
C22 C21 1.399(5) . ?
C22 H22 0.9500 . ?
C6 C5 1.520(5) . ?
C9 C10 1.380(5) . ?
C9 H9 0.9500 . ?
N5 C18 1.441(5) . ?
N5 C15 1.441(6) . ?
N5 C14 1.463(7) . ?
C21 C26 1.406(4) . ?
C11 C10 1.403(5) . ?
C11 H11 0.9500 . ?
C10 H10 0.9500 . ?
C26 C25 1.381(5) . ?
C23 C24 1.396(5) . ?
C23 H23 0.9500 . ?
C5 C4 1.537(5) . ?
C5 H5 1.0000 . ?
C24 C25 1.382(5) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C19 C18 1.508(5) . ?
C4 C3 1.524(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C18 C17 1.590(7) . ?
C18 H18 1.0000 . ?
C15 C16 1.537(8) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C2 C3 1.479(8) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C17 C16 1.475(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N4 C13 104.1(3) . . ?
C19 N6 C20 126.6(3) . . ?
C19 N6 H3 122(3) . . ?
C20 N6 H3 110(3) . . ?
C7 N3 C8 105.6(3) . . ?
C7 N3 H1 129(3) . . ?
C8 N3 H1 125(2) . . ?
C20 N7 C21 106.4(3) . . ?
C20 N7 H2 126(3) . . ?
C21 N7 H2 128(3) . . ?
C20 N8 C26 104.6(3) . . ?
C1 N1 C2 112.7(4) . . ?
C1 N1 C5 113.3(3) . . ?
C2 N1 C5 104.4(3) . . ?
C6 N2 C7 125.8(3) . . ?
C6 N2 H4 110(3) . . ?
C7 N2 H4 122(3) . . ?
N3 C8 C9 131.9(3) . . ?
N3 C8 C13 105.8(3) . . ?
C9 C8 C13 122.3(3) . . ?
N4 C7 N3 114.8(3) . . ?
N4 C7 N2 123.1(3) . . ?
N3 C7 N2 122.1(3) . . ?
N4 C13 C12 130.4(3) . . ?
N4 C13 C8 109.6(3) . . ?
C12 C13 C8 119.9(3) . . ?
C11 C12 C13 118.1(3) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
C23 C22 C21 116.9(3) . . ?
C23 C22 H22 121.6 . . ?
C21 C22 H22 121.6 . . ?
O1 C6 N2 123.9(3) . . ?
O1 C6 C5 121.9(3) . . ?
N2 C6 C5 114.2(3) . . ?
C10 C9 C8 116.8(3) . . ?
C10 C9 H9 121.6 . . ?
C8 C9 H9 121.6 . . ?
N8 C20 N7 113.8(3) . . ?
N8 C20 N6 121.9(3) . . ?
N7 C20 N6 124.2(3) . . ?
C18 N5 C15 108.7(4) . . ?
C18 N5 C14 113.2(4) . . ?
C15 N5 C14 112.1(4) . . ?
N7 C21 C22 132.6(3) . . ?
N7 C21 C26 106.0(3) . . ?
C22 C21 C26 121.4(3) . . ?
C12 C11 C10 121.1(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C9 C10 C11 121.8(3) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C25 C26 N8 130.0(3) . . ?
C25 C26 C21 120.8(3) . . ?
N8 C26 C21 109.1(3) . . ?
C22 C23 C24 121.5(3) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
N1 C5 C6 113.0(3) . . ?
N1 C5 C4 105.6(3) . . ?
C6 C5 C4 110.4(3) . . ?
N1 C5 H5 109.2 . . ?
C6 C5 H5 109.2 . . ?
C4 C5 H5 109.2 . . ?
C25 C24 C23 121.5(3) . . ?
C25 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
C26 C25 C24 118.0(3) . . ?
C26 C25 H25 121.0 . . ?
C24 C25 H25 121.0 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C19 N6 122.5(3) . . ?
O2 C19 C18 122.4(3) . . ?
N6 C19 C18 115.0(3) . . ?
C3 C4 C5 104.9(3) . . ?
C3 C4 H4A 110.8 . . ?
C5 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
C5 C4 H4B 110.8 . . ?
H4A C4 H4B 108.8 . . ?
N5 C18 C19 112.1(3) . . ?
N5 C18 C17 102.9(3) . . ?
C19 C18 C17 110.8(3) . . ?
N5 C18 H18 110.3 . . ?
C19 C18 H18 110.3 . . ?
C17 C18 H18 110.3 . . ?
N5 C15 C16 101.3(4) . . ?
N5 C15 H15A 111.5 . . ?
C16 C15 H15A 111.5 . . ?
N5 C15 H15B 111.5 . . ?
C16 C15 H15B 111.5 . . ?
H15A C15 H15B 109.3 . . ?
N1 C2 C3 104.4(4) . . ?
N1 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
N1 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C16 C17 C18 105.2(4) . . ?
C16 C17 H17A 110.7 . . ?
C18 C17 H17A 110.7 . . ?
C16 C17 H17B 110.7 . . ?
C18 C17 H17B 110.7 . . ?
H17A C17 H17B 108.8 . . ?
C17 C16 C15 101.5(4) . . ?
C17 C16 H16A 111.5 . . ?
C15 C16 H16A 111.5 . . ?
C17 C16 H16B 111.5 . . ?
C15 C16 H16B 111.5 . . ?
H16A C16 H16B 109.3 . . ?
C2 C3 C4 103.5(4) . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
C4 C3 H3B 111.1 . . ?
H3A C3 H3B 109.0 . . ?
N5 C14 H14A 109.5 . . ?
N5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_refine_diff_density_max         0.353
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.040

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

data_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1952636'
loop_
_audit_author_name
_audit_author_address
'Jeppe Christensen '
;national crystallography service (southampton) and diamond light source (didcot)
United Kingdom
;
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H22 N4 O3'
_chemical_formula_sum            'C16 H22 N4 O3'
_chemical_formula_weight         318.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0060 0.0030 '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 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0200 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   8.9903(5)
_cell_length_b                   10.1684(6)
_cell_length_c                   10.7191(7)
_cell_angle_alpha                104.553(6)
_cell_angle_beta                 110.229(6)
_cell_angle_gamma                105.243(6)
_cell_volume                     821.31(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2521
_cell_measurement_theta_max      34.7240090427
_cell_measurement_theta_min      2.83970862676

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.045
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.165
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_T_min  0.998
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CCP4 7.0.040: AIMLESS, version 0.5.32 : 29/03/17
Scaling & analysis of unmerged intensities, 
absorption correction using spherical harmonics
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_dtime           0.004
_diffrn_detector_type            'Dectris, PILATUS 2M'
_diffrn_measurement_details      
;Data collection strategy using shutter-less operation of detector. 
Three omega scans -170 to 25 with phi 0, 120 and 240 respectively.
0.1 degree images with 0.5 sec exposure
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_details 'custom build fixed Chi diffractometer'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_radiation_collimation    'focusing mirrors and 0.100 mm pinhole'
_diffrn_radiation_monochromator  'Si 111, double crystal monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_source_type              'DLS beamline I19, undulator'
_diffrn_radiation_wavelength     0.9028
_diffrn_radiation_wavelength_determination estimated

_diffrn_radiation_wavelength_details 'Au L2 absorption edge'
_diffrn_reflns_number            7772
_diffrn_reflns_av_unetI/netI     0.1847
_diffrn_reflns_av_R_equivalents  0.1676
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.849
_diffrn_reflns_theta_max         35.839
_diffrn_reflns_theta_full        32.798
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.755
_diffrn_reflns_point_group_measured_fraction_full 0.853
_reflns_number_total             5673
_reflns_number_gt                4413
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_max     0.634
_reflns_Friedel_fraction_full    0.745

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'GDA 8.44; generic data acquisition software'
_computing_cell_refinement       
'XIA2 0.4.0.438-g4431aaa, Winter, G. (2010) J. Appl. Cryst. 43'
_computing_data_reduction        
'XIA2 0.4.0.438-g4431aaa, Winter, G. (2010) J. Appl. Cryst. 43'
_computing_structure_solution    'SHELXT Acta Cryst. (2015). A71, 3-8'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1445 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         5673
_refine_ls_number_parameters     455
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0767
_refine_ls_wR_factor_ref         0.2073
_refine_ls_wR_factor_gt          0.1904
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_restrained_S_all      0.955
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 1.9191(5) 1.3825(4) 1.5965(4) 0.0506(10) Uani 1 1 d . . . . .
O3 O 1.8551(5) 1.6951(4) 1.7165(4) 0.0467(9) Uani 1 1 d . . . . .
N4 N 1.5835(5) 1.6511(4) 1.6669(5) 0.0450(12) Uani 1 1 d . . . . .
C22 C 1.7918(7) 1.3347(5) 1.6167(6) 0.0443(13) Uani 1 1 d . . . . .
N2 N 1.3760(6) 1.6772(4) 1.4724(5) 0.0490(12) Uani 1 1 d . . . . .
N3 N 1.3061(7) 1.5874(5) 1.6334(6) 0.0520(14) Uani 1 1 d . . . . .
O6 O 1.1516(4) 1.3012(4) 1.2877(4) 0.0463(9) Uani 1 1 d . . . . .
C16 C 2.1164(7) 1.9940(6) 1.8894(7) 0.0505(14) Uani 1 1 d . . . . .
H28 H 2.0815 1.9453 1.9455 0.061 Uiso 1 1 calc R U . . .
C7 C 1.4246(7) 1.6383(5) 1.5914(6) 0.0454(14) Uani 1 1 d . . . . .
O5 O 1.3041(5) 1.2552(4) 1.4763(4) 0.0483(10) Uani 1 1 d . . . . .
N7 N 1.6993(6) 1.4082(4) 1.3687(5) 0.0455(11) Uani 1 1 d . . . . .
C15 C 2.1967(7) 2.1466(6) 1.9455(6) 0.0523(14) Uani 1 1 d . . . . .
H29 H 2.2176 2.2021 2.0399 0.063 Uiso 1 1 calc R U . . .
N6 N 1.6333(6) 1.3230(4) 1.5318(5) 0.0425(11) Uani 1 1 d . . . . .
C27 C 0.9208(7) 1.0835(6) 1.2549(6) 0.0438(12) Uani 1 1 d . . . . .
C14 C 2.2462(7) 2.2177(6) 1.8628(7) 0.0528(15) Uani 1 1 d . . . . .
H30 H 2.2997 2.3221 1.9004 0.063 Uiso 1 1 calc R U . . .
C28 C 0.8761(8) 1.0093(6) 1.3372(7) 0.0558(15) Uani 1 1 d . . . . .
H16 H 0.8991 1.0642 1.4324 0.067 Uiso 1 1 calc R U . . .
C9 C 1.7090(7) 1.7011(5) 1.6271(6) 0.0424(13) Uani 1 1 d . . . . .
C25 C 1.2997(7) 1.2974(5) 1.3777(6) 0.0441(14) Uani 1 1 d . . . . .
C10 C 2.0018(7) 1.7468(6) 1.6912(6) 0.0483(14) Uani 1 1 d . . . . .
H26A H 1.9660 1.7093 1.5865 0.058 Uiso 1 1 calc R U . . .
H26B H 2.0862 1.7064 1.7352 0.058 Uiso 1 1 calc R U . . .
C24 C 1.6603(8) 1.4522(7) 1.2463(6) 0.0535(15) Uani 1 1 d . . . . .
H8A H 1.6094 1.5258 1.2594 0.080 Uiso 1 1 calc R U . . .
H8B H 1.5790 1.3660 1.1586 0.080 Uiso 1 1 calc R U . . .
H8C H 1.7663 1.4946 1.2382 0.080 Uiso 1 1 calc R U . . .
C11 C 2.0866(7) 1.9116(6) 1.7511(6) 0.0472(13) Uani 1 1 d . . . . .
C23 C 1.5819(7) 1.3597(5) 1.4119(6) 0.0431(14) Uani 1 1 d . . . . .
C29 C 0.7992(9) 0.8583(7) 1.2839(7) 0.0630(18) Uani 1 1 d . . . . .
H15 H 0.7704 0.8095 1.3421 0.076 Uiso 1 1 calc R U . . .
O1 O 1.0858(6) 1.6071(5) 1.4042(4) 0.0646(12) Uani 1 1 d . . . . .
C21 C 1.7998(7) 1.2724(6) 1.7327(6) 0.0479(13) Uani 1 1 d . . . . .
H5 H 1.9176 1.3240 1.8145 0.057 Uiso 1 1 calc R U . . .
C20 C 1.7581(8) 1.1024(6) 1.6733(7) 0.0555(14) Uani 1 1 d . . . . .
H4A H 1.6889 1.0581 1.5678 0.067 Uiso 1 1 calc R U . . .
H4B H 1.8649 1.0830 1.6980 0.067 Uiso 1 1 calc R U . . .
N8 N 1.4242(6) 1.3475(4) 1.3378(5) 0.0437(11) Uani 1 1 d . . . . .
C26 C 1.0035(7) 1.2498(6) 1.3149(6) 0.0479(14) Uani 1 1 d . . . . .
H10A H 0.9182 1.2892 1.2706 0.057 Uiso 1 1 calc R U . . .
H10B H 1.0398 1.2876 1.4198 0.057 Uiso 1 1 calc R U . . .
C31 C 0.8055(7) 0.8497(6) 1.0607(7) 0.0526(15) Uani 1 1 d . . . . .
H13 H 0.7810 0.7948 0.9651 0.063 Uiso 1 1 calc R U . . .
N5 N 1.6747(6) 1.2839(5) 1.7859(5) 0.0512(11) Uani 1 1 d . . . . .
C32 C 0.8821(7) 1.0006(6) 1.1145(6) 0.0470(13) Uani 1 1 d . . . . .
H12 H 0.9090 1.0490 1.0554 0.056 Uiso 1 1 calc R U . . .
C13 C 2.2181(8) 2.1374(6) 1.7259(6) 0.0545(16) Uani 1 1 d . . . . .
H31 H 2.2534 2.1863 1.6703 0.065 Uiso 1 1 calc R U . . .
C12 C 2.1378(7) 1.9848(6) 1.6703(7) 0.0535(15) Uani 1 1 d . . . . .
H32 H 2.1177 1.9300 1.5760 0.064 Uiso 1 1 calc R U . . .
C30 C 0.7637(8) 0.7773(6) 1.1438(7) 0.0578(16) Uani 1 1 d . . . . .
H14 H 0.7112 0.6729 1.1060 0.069 Uiso 1 1 calc R U . . .
C8 C 1.3411(8) 1.5380(7) 1.7511(8) 0.0604(17) Uani 1 1 d . . . . .
H24A H 1.4163 1.6227 1.8415 0.091 Uiso 1 1 calc R U . . .
H24B H 1.3978 1.4688 1.7387 0.091 Uiso 1 1 calc R U . . .
H24C H 1.2330 1.4887 1.7531 0.091 Uiso 1 1 calc R U . . .
C19 C 1.6561(9) 1.0422(6) 1.7484(7) 0.0606(16) Uani 1 1 d . . . . .
H3A H 1.5353 0.9795 1.6787 0.073 Uiso 1 1 calc R U . . .
H3B H 1.7074 0.9834 1.7973 0.073 Uiso 1 1 calc R U . . .
C6 C 1.2117(8) 1.6559(8) 1.3846(7) 0.0611(18) Uani 1 1 d . . . . .
C18 C 1.6664(9) 1.1775(6) 1.8568(7) 0.0543(14) Uani 1 1 d . . . . .
H2A H 1.5635 1.1562 1.8749 0.065 Uiso 1 1 calc R U . . .
H2B H 1.7703 1.2143 1.9489 0.065 Uiso 1 1 calc R U . . .
C17 C 1.7184(9) 1.4318(6) 1.8815(7) 0.0614(18) Uani 1 1 d . . . . .
H1A H 1.7282 1.4992 1.8308 0.092 Uiso 1 1 calc R U . . .
H1B H 1.8281 1.4633 1.9654 0.092 Uiso 1 1 calc R U . . .
H1C H 1.6283 1.4329 1.9129 0.092 Uiso 1 1 calc R U . . .
C2 C 1.320(4) 1.7783(15) 1.134(3) 0.061(3) Uani 0.523(5) 1 d D . P A 1
H18A H 1.4352 1.8350 1.1458 0.073 Uiso 0.523(5) 1 calc R U P A 1
H18B H 1.2363 1.8136 1.0800 0.073 Uiso 0.523(5) 1 calc R U P A 1
C1 C 1.3130(18) 1.9356(12) 1.3423(19) 0.060(4) Uani 0.523(5) 1 d D . P A 1
H17A H 1.1998 1.9349 1.2877 0.091 Uiso 0.523(5) 1 calc R U P A 1
H17B H 1.4022 2.0171 1.3443 0.091 Uiso 0.523(5) 1 calc R U P A 1
H17C H 1.3305 1.9482 1.4407 0.091 Uiso 0.523(5) 1 calc R U P A 1
C5 C 1.1860(17) 1.6636(12) 1.2517(15) 0.051(2) Uani 0.523(5) 1 d D . P A 1
H21 H 1.0719 1.6697 1.2053 0.061 Uiso 0.523(5) 1 calc R U P A 1
N1 N 1.3225(11) 1.7963(9) 1.2740(9) 0.0497(15) Uani 0.523(5) 1 d D . P A 1
C4 C 1.2019(15) 1.5403(10) 1.1450(11) 0.0550(14) Uani 0.523(5) 1 d D . P A 1
H20A H 1.2835 1.5017 1.1968 0.066 Uiso 0.523(5) 1 calc R U P A 1
H20B H 1.0889 1.4582 1.0827 0.066 Uiso 0.523(5) 1 calc R U P A 1
C3 C 1.2688(14) 1.6147(11) 1.0562(12) 0.0550(14) Uani 0.523(5) 1 d D . P A 1
H19A H 1.3689 1.5938 1.0521 0.066 Uiso 0.523(5) 1 calc R U P A 1
H19B H 1.1780 1.5798 0.9570 0.066 Uiso 0.523(5) 1 calc R U P A 1
C5A C 1.214(2) 1.7342(14) 1.2654(19) 0.051(2) Uani 0.477(5) 1 d D . P A 2
H21A H 1.0982 1.6857 1.1810 0.061 Uiso 0.477(5) 1 calc R U P A 2
C4A C 1.259(3) 1.9009(17) 1.324(2) 0.0550(14) Uani 0.477(5) 1 d D . P A 2
H20C H 1.3257 1.9440 1.4294 0.066 Uiso 0.477(5) 1 calc R U P A 2
H20D H 1.1528 1.9220 1.2981 0.066 Uiso 0.477(5) 1 calc R U P A 2
C1A C 1.2939(15) 1.5687(12) 1.1164(14) 0.044(3) Uani 0.477(5) 1 d D . P A 2
H17D H 1.1812 1.5371 1.0358 0.066 Uiso 0.477(5) 1 calc R U P A 2
H17E H 1.2886 1.5018 1.1679 0.066 Uiso 0.477(5) 1 calc R U P A 2
H17F H 1.3797 1.5668 1.0799 0.066 Uiso 0.477(5) 1 calc R U P A 2
N1A N 1.3423(13) 1.7194(10) 1.2148(11) 0.0497(15) Uani 0.477(5) 1 d D . P A 2
C2A C 1.355(4) 1.8287(18) 1.141(3) 0.061(3) Uani 0.477(5) 1 d D . P A 2
H18C H 1.2524 1.7934 1.0481 0.073 Uiso 0.477(5) 1 calc R U P A 2
H18D H 1.4592 1.8487 1.1238 0.073 Uiso 0.477(5) 1 calc R U P A 2
C3A C 1.3667(18) 1.9643(13) 1.2508(14) 0.0550(14) Uani 0.477(5) 1 d D . P A 2
H19C H 1.3185 2.0254 1.2034 0.066 Uiso 0.477(5) 1 calc R U P A 2
H19D H 1.4874 2.0250 1.3222 0.066 Uiso 0.477(5) 1 calc R U P A 2
O2 O 1.7030(5) 1.7447(4) 1.5300(4) 0.0489(10) Uani 1 1 d . . . . .
H33 H 1.548(7) 1.292(6) 1.548(5) 0.030(13) Uiso 1 1 d . . . . .
H34 H 1.806(8) 1.425(6) 1.435(6) 0.042(15) Uiso 1 1 d . . . . .
H35 H 1.213(9) 1.583(8) 1.592(7) 0.06(2) Uiso 1 1 d . . . . .
H36 H 1.472(7) 1.699(6) 1.441(6) 0.045(15) 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
O4 C22 1.235(7) . ?
O3 C9 1.360(6) . ?
O3 C10 1.429(7) . ?
N4 C7 1.327(7) . ?
N4 C9 1.361(7) . ?
C22 N6 1.354(7) . ?
C22 C21 1.520(9) . ?
N2 C6 1.372(8) . ?
N2 C7 1.391(8) . ?
N2 H36 1.02(6) . ?
N3 C7 1.329(7) . ?
N3 C8 1.439(9) . ?
N3 H35 0.78(7) . ?
O6 C25 1.365(7) . ?
O6 C26 1.453(7) . ?
C16 C15 1.391(7) . ?
C16 C11 1.398(8) . ?
C16 H28 0.9500 . ?
O5 C25 1.229(7) . ?
N7 C23 1.323(7) . ?
N7 C24 1.451(7) . ?
N7 H34 0.91(6) . ?
C15 C14 1.390(9) . ?
C15 H29 0.9500 . ?
N6 C23 1.388(7) . ?
N6 H33 0.84(6) . ?
C27 C28 1.388(9) . ?
C27 C32 1.394(8) . ?
C27 C26 1.512(7) . ?
C14 C13 1.384(8) . ?
C14 H30 0.9500 . ?
C28 C29 1.375(9) . ?
C28 H16 0.9500 . ?
C9 O2 1.221(7) . ?
C25 N8 1.355(7) . ?
C10 C11 1.500(7) . ?
C10 H26A 0.9900 . ?
C10 H26B 0.9900 . ?
C24 H8A 0.9800 . ?
C24 H8B 0.9800 . ?
C24 H8C 0.9800 . ?
C11 C12 1.392(9) . ?
C23 N8 1.317(7) . ?
C29 C30 1.395(8) . ?
C29 H15 0.9500 . ?
O1 C6 1.222(8) . ?
C21 N5 1.444(8) . ?
C21 C20 1.573(7) . ?
C21 H5 1.0000 . ?
C20 C19 1.526(9) . ?
C20 H4A 0.9900 . ?
C20 H4B 0.9900 . ?
C26 H10A 0.9900 . ?
C26 H10B 0.9900 . ?
C31 C32 1.373(7) . ?
C31 C30 1.376(9) . ?
C31 H13 0.9500 . ?
N5 C17 1.451(7) . ?
N5 C18 1.470(8) . ?
C32 H12 0.9500 . ?
C13 C12 1.390(8) . ?
C13 H31 0.9500 . ?
C12 H32 0.9500 . ?
C30 H14 0.9500 . ?
C8 H24A 0.9800 . ?
C8 H24B 0.9800 . ?
C8 H24C 0.9800 . ?
C19 C18 1.519(8) . ?
C19 H3A 0.9900 . ?
C19 H3B 0.9900 . ?
C6 C5 1.388(15) . ?
C6 C5A 1.670(17) . ?
C18 H2A 0.9900 . ?
C18 H2B 0.9900 . ?
C17 H1A 0.9800 . ?
C17 H1B 0.9800 . ?
C17 H1C 0.9800 . ?
C2 N1 1.45(2) . ?
C2 C3 1.520(16) . ?
C2 H18A 0.9900 . ?
C2 H18B 0.9900 . ?
C1 N1 1.461(14) . ?
C1 H17A 0.9800 . ?
C1 H17B 0.9800 . ?
C1 H17C 0.9800 . ?
C5 N1 1.466(14) . ?
C5 C4 1.545(14) . ?
C5 H21 1.0000 . ?
C4 C3 1.537(15) . ?
C4 H20A 0.9900 . ?
C4 H20B 0.9900 . ?
C3 H19A 0.9900 . ?
C3 H19B 0.9900 . ?
C5A N1A 1.46(2) . ?
C5A C4A 1.537(18) . ?
C5A H21A 1.0000 . ?
C4A C3A 1.55(2) . ?
C4A H20C 0.9900 . ?
C4A H20D 0.9900 . ?
C1A N1A 1.473(13) . ?
C1A H17D 0.9800 . ?
C1A H17E 0.9800 . ?
C1A H17F 0.9800 . ?
N1A C2A 1.52(2) . ?
C2A C3A 1.527(19) . ?
C2A H18C 0.9900 . ?
C2A H18D 0.9900 . ?
C3A H19C 0.9900 . ?
C3A H19D 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O3 C10 115.5(5) . . ?
C7 N4 C9 120.2(5) . . ?
O4 C22 N6 123.2(5) . . ?
O4 C22 C21 121.7(5) . . ?
N6 C22 C21 114.9(5) . . ?
C6 N2 C7 125.9(6) . . ?
C6 N2 H36 121(3) . . ?
C7 N2 H36 111(3) . . ?
C7 N3 C8 122.7(5) . . ?
C7 N3 H35 119(5) . . ?
C8 N3 H35 118(5) . . ?
C25 O6 C26 115.8(5) . . ?
C15 C16 C11 120.5(6) . . ?
C15 C16 H28 119.8 . . ?
C11 C16 H28 119.8 . . ?
N4 C7 N3 118.0(6) . . ?
N4 C7 N2 123.8(5) . . ?
N3 C7 N2 118.2(5) . . ?
C23 N7 C24 122.0(5) . . ?
C23 N7 H34 110(4) . . ?
C24 N7 H34 127(4) . . ?
C14 C15 C16 119.7(5) . . ?
C14 C15 H29 120.2 . . ?
C16 C15 H29 120.2 . . ?
C22 N6 C23 128.8(5) . . ?
C22 N6 H33 122(3) . . ?
C23 N6 H33 109(4) . . ?
C28 C27 C32 118.1(5) . . ?
C28 C27 C26 120.7(5) . . ?
C32 C27 C26 121.2(5) . . ?
C13 C14 C15 120.4(5) . . ?
C13 C14 H30 119.8 . . ?
C15 C14 H30 119.8 . . ?
C29 C28 C27 121.5(5) . . ?
C29 C28 H16 119.3 . . ?
C27 C28 H16 119.3 . . ?
O2 C9 N4 129.8(5) . . ?
O2 C9 O3 122.0(5) . . ?
N4 C9 O3 108.2(5) . . ?
O5 C25 N8 130.9(5) . . ?
O5 C25 O6 120.6(5) . . ?
N8 C25 O6 108.5(5) . . ?
O3 C10 C11 112.9(4) . . ?
O3 C10 H26A 109.0 . . ?
C11 C10 H26A 109.0 . . ?
O3 C10 H26B 109.0 . . ?
C11 C10 H26B 109.0 . . ?
H26A C10 H26B 107.8 . . ?
N7 C24 H8A 109.5 . . ?
N7 C24 H8B 109.5 . . ?
H8A C24 H8B 109.5 . . ?
N7 C24 H8C 109.5 . . ?
H8A C24 H8C 109.5 . . ?
H8B C24 H8C 109.5 . . ?
C12 C11 C16 118.9(5) . . ?
C12 C11 C10 120.6(5) . . ?
C16 C11 C10 120.5(5) . . ?
N8 C23 N7 118.3(5) . . ?
N8 C23 N6 124.3(5) . . ?
N7 C23 N6 117.4(5) . . ?
C28 C29 C30 119.5(6) . . ?
C28 C29 H15 120.2 . . ?
C30 C29 H15 120.2 . . ?
N5 C21 C22 113.9(5) . . ?
N5 C21 C20 104.0(5) . . ?
C22 C21 C20 111.2(5) . . ?
N5 C21 H5 109.2 . . ?
C22 C21 H5 109.2 . . ?
C20 C21 H5 109.2 . . ?
C19 C20 C21 103.7(5) . . ?
C19 C20 H4A 111.0 . . ?
C21 C20 H4A 111.0 . . ?
C19 C20 H4B 111.0 . . ?
C21 C20 H4B 111.0 . . ?
H4A C20 H4B 109.0 . . ?
C23 N8 C25 120.2(5) . . ?
O6 C26 C27 111.6(4) . . ?
O6 C26 H10A 109.3 . . ?
C27 C26 H10A 109.3 . . ?
O6 C26 H10B 109.3 . . ?
C27 C26 H10B 109.3 . . ?
H10A C26 H10B 108.0 . . ?
C32 C31 C30 120.7(5) . . ?
C32 C31 H13 119.7 . . ?
C30 C31 H13 119.7 . . ?
C21 N5 C17 113.3(5) . . ?
C21 N5 C18 104.1(4) . . ?
C17 N5 C18 112.6(5) . . ?
C31 C32 C27 120.7(6) . . ?
C31 C32 H12 119.6 . . ?
C27 C32 H12 119.6 . . ?
C14 C13 C12 119.8(6) . . ?
C14 C13 H31 120.1 . . ?
C12 C13 H31 120.1 . . ?
C13 C12 C11 120.7(5) . . ?
C13 C12 H32 119.6 . . ?
C11 C12 H32 119.6 . . ?
C31 C30 C29 119.5(5) . . ?
C31 C30 H14 120.2 . . ?
C29 C30 H14 120.2 . . ?
N3 C8 H24A 109.5 . . ?
N3 C8 H24B 109.5 . . ?
H24A C8 H24B 109.5 . . ?
N3 C8 H24C 109.5 . . ?
H24A C8 H24C 109.5 . . ?
H24B C8 H24C 109.5 . . ?
C18 C19 C20 104.9(5) . . ?
C18 C19 H3A 110.8 . . ?
C20 C19 H3A 110.8 . . ?
C18 C19 H3B 110.8 . . ?
C20 C19 H3B 110.8 . . ?
H3A C19 H3B 108.8 . . ?
O1 C6 N2 124.9(7) . . ?
O1 C6 C5 118.3(7) . . ?
N2 C6 C5 115.5(8) . . ?
O1 C6 C5A 124.3(7) . . ?
N2 C6 C5A 110.0(8) . . ?
N5 C18 C19 103.0(5) . . ?
N5 C18 H2A 111.2 . . ?
C19 C18 H2A 111.2 . . ?
N5 C18 H2B 111.2 . . ?
C19 C18 H2B 111.2 . . ?
H2A C18 H2B 109.1 . . ?
N5 C17 H1A 109.5 . . ?
N5 C17 H1B 109.5 . . ?
H1A C17 H1B 109.5 . . ?
N5 C17 H1C 109.5 . . ?
H1A C17 H1C 109.5 . . ?
H1B C17 H1C 109.5 . . ?
N1 C2 C3 106.5(11) . . ?
N1 C2 H18A 110.4 . . ?
C3 C2 H18A 110.4 . . ?
N1 C2 H18B 110.4 . . ?
C3 C2 H18B 110.4 . . ?
H18A C2 H18B 108.6 . . ?
N1 C1 H17A 109.5 . . ?
N1 C1 H17B 109.5 . . ?
H17A C1 H17B 109.5 . . ?
N1 C1 H17C 109.5 . . ?
H17A C1 H17C 109.5 . . ?
H17B C1 H17C 109.5 . . ?
C6 C5 N1 108.4(10) . . ?
C6 C5 C4 116.9(9) . . ?
N1 C5 C4 102.7(9) . . ?
C6 C5 H21 109.5 . . ?
N1 C5 H21 109.5 . . ?
C4 C5 H21 109.5 . . ?
C2 N1 C1 112.8(11) . . ?
C2 N1 C5 106.1(11) . . ?
C1 N1 C5 115.3(9) . . ?
C3 C4 C5 104.6(8) . . ?
C3 C4 H20A 110.8 . . ?
C5 C4 H20A 110.8 . . ?
C3 C4 H20B 110.8 . . ?
C5 C4 H20B 110.8 . . ?
H20A C4 H20B 108.9 . . ?
C2 C3 C4 104.8(10) . . ?
C2 C3 H19A 110.8 . . ?
C4 C3 H19A 110.8 . . ?
C2 C3 H19B 110.8 . . ?
C4 C3 H19B 110.8 . . ?
H19A C3 H19B 108.9 . . ?
N1A C5A C4A 104.2(12) . . ?
N1A C5A C6 112.4(10) . . ?
C4A C5A C6 114.4(13) . . ?
N1A C5A H21A 108.5 . . ?
C4A C5A H21A 108.5 . . ?
C6 C5A H21A 108.5 . . ?
C5A C4A C3A 105.1(14) . . ?
C5A C4A H20C 110.7 . . ?
C3A C4A H20C 110.7 . . ?
C5A C4A H20D 110.7 . . ?
C3A C4A H20D 110.7 . . ?
H20C C4A H20D 108.8 . . ?
N1A C1A H17D 109.5 . . ?
N1A C1A H17E 109.5 . . ?
H17D C1A H17E 109.5 . . ?
N1A C1A H17F 109.5 . . ?
H17D C1A H17F 109.5 . . ?
H17E C1A H17F 109.5 . . ?
C5A N1A C1A 113.0(10) . . ?
C5A N1A C2A 103.7(12) . . ?
C1A N1A C2A 111.7(12) . . ?
N1A C2A C3A 101.3(15) . . ?
N1A C2A H18C 111.5 . . ?
C3A C2A H18C 111.5 . . ?
N1A C2A H18D 111.5 . . ?
C3A C2A H18D 111.5 . . ?
H18C C2A H18D 109.3 . . ?
C2A C3A C4A 104.5(12) . . ?
C2A C3A H19C 110.8 . . ?
C4A C3A H19C 110.8 . . ?
C2A C3A H19D 110.8 . . ?
C4A C3A H19D 110.8 . . ?
H19C C3A H19D 108.9 . . ?

_refine_diff_density_max         0.442
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_2017ncs0423
_database_code_depnum_ccdc_archive 'CCDC 1952634'
loop_
_audit_author_name
_audit_author_address
'Jeppe Christensen '
;national crystallography service (southampton) and diamond light source (didcot)
United Kingdom
;
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H22 N4 O3'
_chemical_formula_sum            'C12 H22 N4 O3'
_chemical_formula_weight         270.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0059 0.0028 '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 0.0109 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0184 0.0104 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.62820(10)
_cell_length_b                   13.8844(2)
_cell_length_c                   11.73000(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.9130(10)
_cell_angle_gamma                90
_cell_volume                     1528.43(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6472
_cell_measurement_theta_max      34.4711522507
_cell_measurement_theta_min      2.25934511021

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.048
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   1.000
_exptl_absorpt_correction_T_min  0.995916484265
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CCP4 7.0.040: AIMLESS, version 0.5.32 : 29/03/17
Scaling & analysis of unmerged intensities, 
absorption correction using spherical harmonics
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_dtime           0.004
_diffrn_detector_type            'Dectris, PILATUS 2M'
_diffrn_measurement_details      
;Data collection strategy using shutter-less operation of detector. 
Three omega scans -170 to 25 with phi 0, 120 and 240 respectively.
0.1 degree images with 0.5 sec exposure
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_details 'custom build fixed Chi diffractometer'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_radiation_collimation    'focusing mirrors and 0.100 mm pinhole'
_diffrn_radiation_monochromator  'Si 111, double crystal monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_source_type              'DLS beamline I19, undulator'
_diffrn_radiation_wavelength     0.9028
_diffrn_radiation_wavelength_determination estimated
_diffrn_radiation_wavelength_details 'Au L2 absorption edge'
_diffrn_reflns_number            14738
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.263
_diffrn_reflns_theta_max         35.896
_diffrn_reflns_theta_full        32.798
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             6228
_reflns_number_gt                4974
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.829
_reflns_Friedel_fraction_max     0.839
_reflns_Friedel_fraction_full    0.953

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'GDA 8.44; generic data acquisition software'
_computing_cell_refinement       
'XIA2 0.4.0.438-g4431aaa, Winter, G. (2010) J. Appl. Cryst. 43'
_computing_data_reduction        
'XIA2 0.4.0.438-g4431aaa, Winter, G. (2010) J. Appl. Cryst. 43'
_computing_structure_solution    'SHELXT Acta Cryst. (2015). A71, 3-8'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1448P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1863 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(5)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         6228
_refine_ls_number_parameters     375
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0747
_refine_ls_wR_factor_ref         0.2109
_refine_ls_wR_factor_gt          0.1979
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.7007(3) 0.6846(2) 0.5182(2) 0.0398(8) Uani 1 1 d . . . . .
O1 O 0.2569(3) 0.3009(2) 0.9628(3) 0.0385(7) Uani 1 1 d . . . . .
O3 O 0.7932(3) 0.5427(2) 0.9274(2) 0.0365(7) Uani 1 1 d . . . . .
O2 O 0.7429(3) 0.4347(2) 1.0572(3) 0.0413(8) Uani 1 1 d . . . . .
N4 N 0.5793(4) 0.4793(2) 0.8862(3) 0.0319(8) Uani 1 1 d . . . . .
O6 O 0.1666(4) 0.4444(3) 0.5584(3) 0.0481(9) Uani 1 1 d . . . . .
O5 O 0.2250(3) 0.5371(3) 0.4174(3) 0.0439(8) Uani 1 1 d . . . . .
N6 N 0.4912(4) 0.6010(3) 0.4738(3) 0.0315(8) Uani 1 1 d . . . . .
N7 N 0.6076(4) 0.5608(3) 0.6627(3) 0.0317(8) Uani 1 1 d . . . . .
N2 N 0.4737(4) 0.3783(3) 1.0069(3) 0.0300(8) Uani 1 1 d . . . . .
N3 N 0.3522(4) 0.4249(3) 0.8213(3) 0.0335(8) Uani 1 1 d . . . . .
N1 N 0.5642(4) 0.2845(3) 1.2045(3) 0.0328(8) Uani 1 1 d . . . . .
N8 N 0.3812(4) 0.5061(3) 0.5977(3) 0.0324(8) Uani 1 1 d . . . . .
C00E C 0.7077(5) 0.4806(3) 0.9664(4) 0.0323(9) Uani 1 1 d . . . . .
C7 C 0.4709(4) 0.4287(3) 0.9036(3) 0.0296(8) Uani 1 1 d . . . . .
C18 C 0.5887(5) 0.6654(3) 0.4505(4) 0.0336(9) Uani 1 1 d . . . . .
C19 C 0.4915(4) 0.5554(3) 0.5783(3) 0.0300(9) Uani 1 1 d . . . . .
C6 C 0.3722(5) 0.3165(3) 1.0297(4) 0.0316(9) Uani 1 1 d . . . . .
C17 C 0.5411(6) 0.7146(3) 0.3316(4) 0.0412(11) Uani 1 1 d . . . . .
H17 H 0.6228 0.7453 0.3057 0.049 Uiso 1 1 calc R U . . .
C1 C 0.6583(5) 0.2082(4) 1.1867(4) 0.0418(11) Uani 1 1 d . . . . .
H1A H 0.6430 0.1941 1.1030 0.063 Uiso 1 1 calc R U . . .
H1B H 0.6388 0.1503 1.2284 0.063 Uiso 1 1 calc R U . . .
H1C H 0.7574 0.2282 1.2167 0.063 Uiso 1 1 calc R U . . .
N5 N 0.4600(6) 0.6517(4) 0.2426(4) 0.0651(14) Uani 1 1 d . . . . .
C8 C 0.9429(5) 0.5583(4) 0.9906(4) 0.0441(12) Uani 1 1 d . . . . .
C5 C 0.4139(5) 0.2691(3) 1.1493(3) 0.0326(9) Uani 1 1 d . . . . .
H7 H 0.3935 0.1985 1.1419 0.039 Uiso 1 1 calc R U . . .
C20 C 0.2558(5) 0.5004(3) 0.5143(4) 0.0361(10) Uani 1 1 d . . . . .
C4 C 0.3288(5) 0.3153(4) 1.2343(4) 0.0422(11) Uani 1 1 d . . . . .
H4A H 0.2558 0.3606 1.1921 0.051 Uiso 1 1 calc R U . . .
H4B H 0.2815 0.2651 1.2721 0.051 Uiso 1 1 calc R U . . .
C3 C 0.4413(6) 0.3679(4) 1.3238(4) 0.0484(12) Uani 1 1 d . . . . .
H3A H 0.4537 0.4348 1.2987 0.058 Uiso 1 1 calc R U . . .
H3B H 0.4162 0.3692 1.4012 0.058 Uiso 1 1 calc R U . . .
C11 C 0.9496(5) 0.5946(4) 1.1127(4) 0.0477(12) Uani 1 1 d . . . . .
H11A H 0.9104 0.5457 1.1571 0.071 Uiso 1 1 calc R U . . .
H11B H 0.8938 0.6540 1.1091 0.071 Uiso 1 1 calc R U . . .
H11C H 1.0490 0.6076 1.1515 0.071 Uiso 1 1 calc R U . . .
C21 C 0.0217(5) 0.4225(4) 0.4913(4) 0.0489(13) Uani 1 1 d . . . . .
C2 C 0.5731(6) 0.3094(4) 1.3278(4) 0.0429(11) Uani 1 1 d . . . . .
H2A H 0.6599 0.3475 1.3599 0.051 Uiso 1 1 calc R U . . .
H2B H 0.5736 0.2508 1.3759 0.051 Uiso 1 1 calc R U . . .
C22 C 0.0291(6) 0.3696(4) 0.3789(5) 0.0520(13) Uani 1 1 d . . . . .
H22A H 0.0968 0.3161 0.3972 0.078 Uiso 1 1 calc R U . . .
H22B H 0.0607 0.4142 0.3251 0.078 Uiso 1 1 calc R U . . .
H22C H -0.0654 0.3445 0.3422 0.078 Uiso 1 1 calc R U . . .
C10 C 0.9905(6) 0.6365(5) 0.9157(5) 0.0622(17) Uani 1 1 d . . . . .
H10A H 0.9266 0.6921 0.9102 0.093 Uiso 1 1 calc R U . . .
H10B H 0.9872 0.6112 0.8372 0.093 Uiso 1 1 calc R U . . .
H10C H 1.0881 0.6564 0.9518 0.093 Uiso 1 1 calc R U . . .
C13 C 0.5553(7) 0.6046(4) 0.1760(5) 0.0607(15) Uani 1 1 d . . . . .
H13A H 0.6066 0.6539 0.1421 0.091 Uiso 1 1 calc R U . . .
H13B H 0.4983 0.5652 0.1133 0.091 Uiso 1 1 calc R U . . .
H13C H 0.6238 0.5635 0.2286 0.091 Uiso 1 1 calc R U . . .
C9 C 1.0252(6) 0.4647(5) 0.9885(5) 0.0607(15) Uani 1 1 d . . . . .
H9A H 1.0129 0.4424 0.9075 0.091 Uiso 1 1 calc R U . . .
H9B H 0.9889 0.4156 1.0344 0.091 Uiso 1 1 calc R U . . .
H9C H 1.1266 0.4758 1.0221 0.091 Uiso 1 1 calc R U . . .
C14 C 0.3573(7) 0.6987(5) 0.1633(4) 0.0686(19) Uani 1 1 d . . . . .
H14A H 0.2862 0.6539 0.1176 0.082 Uiso 1 1 calc R U . . .
H14B H 0.3980 0.7395 0.1097 0.082 Uiso 1 1 calc R U . . .
C24 C -0.0655(6) 0.5127(5) 0.4696(6) 0.0692(18) Uani 1 1 d . . . . .
H24A H -0.0267 0.5553 0.4178 0.104 Uiso 1 1 calc R U . . .
H24B H -0.0626 0.5454 0.5441 0.104 Uiso 1 1 calc R U . . .
H24C H -0.1643 0.4963 0.4326 0.104 Uiso 1 1 calc R U . . .
C16 C 0.4153(8) 0.7929(5) 0.3381(5) 0.0639(16) Uani 1 1 d . . . . .
H16A H 0.3979 0.7949 0.4181 0.077 Uiso 1 1 calc R U . . .
H16B H 0.4441 0.8581 0.3180 0.077 Uiso 1 1 calc R U . . .
C23 C -0.0316(7) 0.3549(7) 0.5746(5) 0.090(3) Uani 1 1 d . . . . .
H23A H -0.0317 0.3887 0.6479 0.135 Uiso 1 1 calc R U . . .
H23B H 0.0313 0.2986 0.5909 0.135 Uiso 1 1 calc R U . . .
H23C H -0.1286 0.3337 0.5387 0.135 Uiso 1 1 calc R U . . .
C15 C 0.2904(7) 0.7637(5) 0.2574(7) 0.0706(19) Uani 1 1 d . . . . .
H15A H 0.2360 0.8198 0.2186 0.085 Uiso 1 1 calc R U . . .
H15B H 0.2281 0.7244 0.2957 0.085 Uiso 1 1 calc R U . . .
H2 H 0.345(4) 0.455(3) 0.753(4) 0.022(10) Uiso 1 1 d . . . . .
H1 H 0.543(5) 0.377(4) 1.060(4) 0.032(13) Uiso 1 1 d . . . . .
H6 H 0.426(5) 0.592(3) 0.435(4) 0.018(12) Uiso 1 1 d . . . . .
H4 H 0.609(5) 0.532(4) 0.731(4) 0.030(11) Uiso 1 1 d . . . . .
H5 H 0.688(5) 0.591(4) 0.652(4) 0.034(12) Uiso 1 1 d . . . . .
H3 H 0.267(6) 0.382(4) 0.830(5) 0.052(15) 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
O4 C18 1.217(5) . ?
O1 C6 1.227(5) . ?
O3 C00E 1.341(5) . ?
O3 C8 1.482(5) . ?
O2 C00E 1.222(5) . ?
N4 C7 1.311(5) . ?
N4 C00E 1.376(5) . ?
O6 C20 1.344(5) . ?
O6 C21 1.472(6) . ?
O5 C20 1.220(5) . ?
N6 C18 1.368(6) . ?
N6 C19 1.380(5) . ?
N6 H6 0.70(4) . ?
N7 C19 1.319(6) . ?
N7 H4 0.89(5) . ?
N7 H5 0.91(5) . ?
N2 C6 1.372(6) . ?
N2 C7 1.394(5) . ?
N2 H1 0.80(5) . ?
N3 C7 1.322(5) . ?
N3 H2 0.90(5) . ?
N3 H3 1.04(6) . ?
N1 C1 1.440(6) . ?
N1 C5 1.463(6) . ?
N1 C2 1.471(5) . ?
N8 C19 1.324(5) . ?
N8 C20 1.376(6) . ?
C18 C17 1.529(6) . ?
C6 C5 1.520(6) . ?
C17 N5 1.449(6) . ?
C17 C16 1.642(8) . ?
C17 H17 1.0000 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N5 C14 1.363(8) . ?
N5 C13 1.484(7) . ?
C8 C11 1.507(7) . ?
C8 C9 1.525(8) . ?
C8 C10 1.530(8) . ?
C5 C4 1.562(6) . ?
C5 H7 1.0000 . ?
C4 C3 1.517(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C3 C2 1.499(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C21 C24 1.497(9) . ?
C21 C23 1.525(8) . ?
C21 C22 1.525(8) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C14 C15 1.663(9) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C16 C15 1.414(10) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00E O3 C8 121.7(3) . . ?
C7 N4 C00E 121.7(3) . . ?
C20 O6 C21 121.6(3) . . ?
C18 N6 C19 127.7(4) . . ?
C18 N6 H6 123(4) . . ?
C19 N6 H6 108(4) . . ?
C19 N7 H4 119(3) . . ?
C19 N7 H5 121(3) . . ?
H4 N7 H5 119(4) . . ?
C6 N2 C7 127.4(4) . . ?
C6 N2 H1 110(3) . . ?
C7 N2 H1 122(3) . . ?
C7 N3 H2 121(3) . . ?
C7 N3 H3 122(3) . . ?
H2 N3 H3 117(4) . . ?
C1 N1 C5 114.9(4) . . ?
C1 N1 C2 114.5(4) . . ?
C5 N1 C2 107.7(3) . . ?
C19 N8 C20 121.2(3) . . ?
O2 C00E O3 124.1(4) . . ?
O2 C00E N4 128.3(4) . . ?
O3 C00E N4 107.6(3) . . ?
N4 C7 N3 119.7(4) . . ?
N4 C7 N2 122.9(4) . . ?
N3 C7 N2 117.4(4) . . ?
O4 C18 N6 124.1(4) . . ?
O4 C18 C17 122.6(4) . . ?
N6 C18 C17 113.3(4) . . ?
N7 C19 N8 118.6(4) . . ?
N7 C19 N6 118.3(4) . . ?
N8 C19 N6 123.1(4) . . ?
O1 C6 N2 124.6(4) . . ?
O1 C6 C5 121.9(4) . . ?
N2 C6 C5 113.5(4) . . ?
N5 C17 C18 113.0(4) . . ?
N5 C17 C16 98.5(5) . . ?
C18 C17 C16 109.2(4) . . ?
N5 C17 H17 111.8 . . ?
C18 C17 H17 111.8 . . ?
C16 C17 H17 111.8 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C14 N5 C17 113.3(5) . . ?
C14 N5 C13 106.9(5) . . ?
C17 N5 C13 110.4(5) . . ?
O3 C8 C11 110.7(4) . . ?
O3 C8 C9 108.6(4) . . ?
C11 C8 C9 112.9(4) . . ?
O3 C8 C10 101.5(4) . . ?
C11 C8 C10 110.7(5) . . ?
C9 C8 C10 111.9(4) . . ?
N1 C5 C6 112.1(3) . . ?
N1 C5 C4 105.4(3) . . ?
C6 C5 C4 110.1(3) . . ?
N1 C5 H7 109.7 . . ?
C6 C5 H7 109.7 . . ?
C4 C5 H7 109.7 . . ?
O5 C20 O6 123.8(4) . . ?
O5 C20 N8 129.0(4) . . ?
O6 C20 N8 107.1(3) . . ?
C3 C4 C5 104.1(4) . . ?
C3 C4 H4A 110.9 . . ?
C5 C4 H4A 110.9 . . ?
C3 C4 H4B 110.9 . . ?
C5 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
C2 C3 C4 103.2(4) . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
C4 C3 H3B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O6 C21 C24 110.3(5) . . ?
O6 C21 C23 101.5(4) . . ?
C24 C21 C23 111.6(5) . . ?
O6 C21 C22 109.9(4) . . ?
C24 C21 C22 112.9(5) . . ?
C23 C21 C22 110.2(6) . . ?
N1 C2 C3 103.5(4) . . ?
N1 C2 H2A 111.1 . . ?
C3 C2 H2A 111.1 . . ?
N1 C2 H2B 111.1 . . ?
C3 C2 H2B 111.1 . . ?
H2A C2 H2B 109.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N5 C13 H13A 109.5 . . ?
N5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N5 C14 C15 97.9(4) . . ?
N5 C14 H14A 112.2 . . ?
C15 C14 H14A 112.2 . . ?
N5 C14 H14B 112.2 . . ?
C15 C14 H14B 112.2 . . ?
H14A C14 H14B 109.8 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C15 C16 C17 107.7(5) . . ?
C15 C16 H16A 110.2 . . ?
C17 C16 H16A 110.2 . . ?
C15 C16 H16B 110.2 . . ?
C17 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C16 C15 C14 101.7(5) . . ?
C16 C15 H15A 111.4 . . ?
C14 C15 H15A 111.4 . . ?
C16 C15 H15B 111.4 . . ?
C14 C15 H15B 111.4 . . ?
H15A C15 H15B 109.3 . . ?

_refine_diff_density_max         1.230
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_2017ncs0244
_database_code_depnum_ccdc_archive 'CCDC 1952633'
loop_
_audit_author_name
_audit_author_address
'Jeppe Christensen '
;national crystallography service (southampton) and diamond light source (didcot)
United Kingdom
;
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H18 N4 O'
_chemical_formula_sum            'C13 H18 N4 O'
_chemical_formula_weight         246.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.98857(9)
_cell_length_b                   11.71525(11)
_cell_length_c                   13.99640(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1309.91(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    15832
_cell_measurement_theta_max      35.702321462
_cell_measurement_theta_min      2.19192923429

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CCP4 7.0.040: AIMLESS, version 0.5.32 : 29/03/17
Scaling & analysis of unmerged intensities, 
absorption correction using spherical harmonics
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_dtime           0.004
_diffrn_detector_type            'Dectris, PILATUS 2M'
_diffrn_measurement_details      
;Data collection strategy using shutter-less operation of detector. 
Three omega scans -170 to 25 with phi 0, 120 and 240 respectively.
0.1 degree images with 0.5 sec exposure
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_details 'custom build fixed Chi diffractometer'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_radiation_collimation    'focusing mirrors and 0.0100 mm pinhole'
_diffrn_radiation_monochromator  'Si 111, double crystal monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_source_type              'DLS beamline I19, undulator'
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_wavelength_determination estimated

_diffrn_radiation_wavelength_details 'Zr absorption edge'
_diffrn_reflns_number            28908
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.821
_diffrn_reflns_theta_max         36.098
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6422
_reflns_number_gt                5776
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_max     0.909
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'GDA 8.44; generic data acquisition software'
_computing_cell_refinement       
'XIA2 0.4.0.438-g4431aaa, Winter, G. (2010) J. Appl. Cryst. 43'
_computing_data_reduction        
'XIA2 0.4.0.438-g4431aaa, Winter, G. (2010) J. Appl. Cryst. 43'
_computing_structure_solution    'SHELXT Acta Cryst. (2015). A71, 3-8'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0826P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2322 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(4)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         6422
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1235
_refine_ls_wR_factor_gt          0.1203
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.61110(11) 0.42595(7) 0.21644(6) 0.02325(16) Uani 1 1 d . . . . .
N3 N 0.48157(13) 0.21811(8) 0.22453(7) 0.02162(17) Uani 1 1 d . . . . .
N2 N 0.70022(11) 0.28774(7) 0.32536(6) 0.01955(16) Uani 1 1 d . . . . .
N4 N 0.57702(12) 0.11120(8) 0.34900(6) 0.02105(17) Uani 1 1 d . . . . .
N1 N 0.82915(12) 0.58623(8) 0.29111(7) 0.02256(17) Uani 1 1 d . . . . .
C7 C 0.58657(13) 0.20961(9) 0.29887(7) 0.01842(17) Uani 1 1 d . . . . .
C6 C 0.69950(13) 0.39208(8) 0.28472(7) 0.01881(17) Uani 1 1 d . . . . .
C8 C 0.66622(13) 0.08435(9) 0.43327(7) 0.01952(17) Uani 1 1 d . . . . .
C13 C 0.72487(15) -0.02717(9) 0.44321(8) 0.02292(19) Uani 1 1 d . . . . .
H13 H 0.7109 -0.0802 0.3925 0.028 Uiso 1 1 calc R U . . .
C5 C 0.82259(14) 0.47196(9) 0.33362(7) 0.02057(18) Uani 1 1 d . . . . .
H5 H 0.9368 0.4373 0.3304 0.025 Uiso 1 1 calc R U . . .
C12 C 0.80390(15) -0.06093(11) 0.52727(9) 0.0270(2) Uani 1 1 d . . . . .
H12 H 0.8431 -0.1371 0.5340 0.032 Uiso 1 1 calc R U . . .
C9 C 0.68725(16) 0.16212(9) 0.50745(7) 0.0233(2) Uani 1 1 d . . . . .
H9 H 0.6468 0.2380 0.5013 0.028 Uiso 1 1 calc R U . . .
C11 C 0.82541(16) 0.01664(11) 0.60126(9) 0.0279(2) Uani 1 1 d . . . . .
H11 H 0.8791 -0.0062 0.6587 0.033 Uiso 1 1 calc R U . . .
C4 C 0.77744(16) 0.49293(10) 0.44007(8) 0.0253(2) Uani 1 1 d . . . . .
H4A H 0.6585 0.4744 0.4524 0.030 Uiso 1 1 calc R U . . .
H4B H 0.8485 0.4459 0.4826 0.030 Uiso 1 1 calc R U . . .
C2 C 0.90317(17) 0.65845(10) 0.36617(10) 0.0291(2) Uani 1 1 d . . . . .
H2A H 0.8840 0.7404 0.3528 0.035 Uiso 1 1 calc R U . . .
H2B H 1.0250 0.6446 0.3720 0.035 Uiso 1 1 calc R U . . .
C10 C 0.76791(16) 0.12796(11) 0.59072(8) 0.0264(2) Uani 1 1 d . . . . .
H10 H 0.7839 0.1813 0.6410 0.032 Uiso 1 1 calc R U . . .
C1 C 0.92756(18) 0.58905(12) 0.20263(10) 0.0323(3) Uani 1 1 d . . . . .
H1A H 1.0405 0.5602 0.2153 0.048 Uiso 1 1 calc R U . . .
H1B H 0.9345 0.6678 0.1792 0.048 Uiso 1 1 calc R U . . .
H1C H 0.8734 0.5411 0.1543 0.048 Uiso 1 1 calc R U . . .
C3 C 0.81104(19) 0.62117(11) 0.45603(9) 0.0311(3) Uani 1 1 d . . . . .
H3A H 0.7048 0.6638 0.4635 0.037 Uiso 1 1 calc R U . . .
H3B H 0.8810 0.6334 0.5135 0.037 Uiso 1 1 calc R U . . .
H1 H 0.486(2) 0.2777(16) 0.1978(13) 0.025(4) Uiso 1 1 d . . . . .
H3 H 0.498(2) 0.0563(19) 0.3294(14) 0.036(5) Uiso 1 1 d . . . . .
H2 H 0.398(3) 0.1703(17) 0.2225(15) 0.040(5) 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
O1 C6 1.2528(12) . ?
N3 C7 1.3403(13) . ?
N3 H1 0.792(19) . ?
N3 H2 0.87(2) . ?
N2 C7 1.3415(13) . ?
N2 C6 1.3482(13) . ?
N4 C7 1.3518(13) . ?
N4 C8 1.4134(13) . ?
N4 H3 0.94(2) . ?
N1 C5 1.4659(13) . ?
N1 C1 1.4672(16) . ?
N1 C2 1.4728(15) . ?
C6 C5 1.5202(15) . ?
C8 C9 1.3916(14) . ?
C8 C13 1.3949(15) . ?
C13 C12 1.3925(16) . ?
C13 H13 0.9500 . ?
C5 C4 1.5525(16) . ?
C5 H5 1.0000 . ?
C12 C11 1.3885(19) . ?
C12 H12 0.9500 . ?
C9 C10 1.3906(15) . ?
C9 H9 0.9500 . ?
C11 C10 1.3905(19) . ?
C11 H11 0.9500 . ?
C4 C3 1.5424(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C2 C3 1.521(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C10 H10 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N3 H1 113.7(13) . . ?
C7 N3 H2 117.0(13) . . ?
H1 N3 H2 126.0(17) . . ?
C7 N2 C6 119.95(9) . . ?
C7 N4 C8 126.47(9) . . ?
C7 N4 H3 118.0(13) . . ?
C8 N4 H3 115.3(13) . . ?
C5 N1 C1 112.47(9) . . ?
C5 N1 C2 104.44(9) . . ?
C1 N1 C2 111.96(10) . . ?
N3 C7 N2 125.97(10) . . ?
N3 C7 N4 115.53(9) . . ?
N2 C7 N4 118.47(9) . . ?
O1 C6 N2 127.69(10) . . ?
O1 C6 C5 120.87(9) . . ?
N2 C6 C5 111.43(9) . . ?
C9 C8 C13 119.88(10) . . ?
C9 C8 N4 122.53(10) . . ?
C13 C8 N4 117.46(9) . . ?
C12 C13 C8 120.17(10) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
N1 C5 C6 113.74(9) . . ?
N1 C5 C4 104.67(9) . . ?
C6 C5 C4 112.28(9) . . ?
N1 C5 H5 108.7 . . ?
C6 C5 H5 108.7 . . ?
C4 C5 H5 108.7 . . ?
C11 C12 C13 120.03(11) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C10 C9 C8 119.53(11) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C12 C11 C10 119.59(11) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C3 C4 C5 104.64(10) . . ?
C3 C4 H4A 110.8 . . ?
C5 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
C5 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
N1 C2 C3 103.33(10) . . ?
N1 C2 H2A 111.1 . . ?
C3 C2 H2A 111.1 . . ?
N1 C2 H2B 111.1 . . ?
C3 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
C9 C10 C11 120.79(11) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C3 C4 104.13(10) . . ?
C2 C3 H3A 110.9 . . ?
C4 C3 H3A 110.9 . . ?
C2 C3 H3B 110.9 . . ?
C4 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?

_refine_diff_density_max         0.528
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.078

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

data_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1952635'
loop_
_audit_author_name
_audit_author_address
'Jeppe Christensen '
;national crystallography service (southampton) and diamond light source (didcot)
United Kingdom
;
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H24 N4 O3'
_chemical_formula_sum            'C13 H24 N4 O3'
_chemical_formula_weight         284.36

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'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   9.1851(3)
_cell_length_b                   9.3856(2)
_cell_length_c                   9.6867(3)
_cell_angle_alpha                68.200(2)
_cell_angle_beta                 89.701(2)
_cell_angle_gamma                86.138(2)
_cell_volume                     773.41(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11418
_cell_measurement_theta_min      4.8060
_cell_measurement_theta_max      69.5390

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_F_000             308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.721
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.61151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measurement_details      
;
Data collection strategy using shutter-less operation of detector. 
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC11 quarter χ goniometer'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_radiation_collimation    '0.3 mm, Varimax focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'Rotating anode'
_diffrn_source_type              'Rigaku 007 HF'
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_source_current           30.0
_diffrn_source_target            Cu
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_reflns_number            26740
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.827
_diffrn_reflns_theta_max         70.430
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_point_group_measured_fraction_full 0.928
_reflns_number_total             5379
_reflns_number_gt                5050
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.851
_reflns_Friedel_fraction_max     0.836
_reflns_Friedel_fraction_full    0.859

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro 1.171.39.31c (Rigaku Oxford Diffraction, 2017)'
_computing_cell_refinement       
'CrysAlisPro 1.171.39.31c (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction        
'CrysAlisPro 1.171.39.31c (Rigaku Oxford Diffraction, 2017)'
_computing_structure_solution    
'SHELXT (G. M. Sheldrick Acta Cryst. (2015). A71, 3-8)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1448P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2158 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(11)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         5379
_refine_ls_number_parameters     387
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1750
_refine_ls_wR_factor_gt          0.1724
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O 1.1608(3) 0.6013(3) 0.7050(2) 0.0312(6) Uani 1 1 d . . . . .
O1 O 0.4004(3) 0.6422(3) 0.4229(3) 0.0331(6) Uani 1 1 d . . . . .
O2 O -0.0670(3) 0.6058(3) 0.1938(3) 0.0347(6) Uani 1 1 d . . . . .
O3 O -0.1597(3) 0.3711(3) 0.2846(3) 0.0327(6) Uani 1 1 d . . . . .
O4 O 0.5990(3) 0.3385(3) 0.5598(3) 0.0329(6) Uani 1 1 d . . . . .
O5 O 1.0672(3) 0.3672(3) 0.7928(3) 0.0348(6) Uani 1 1 d . . . . .
N2 N 0.1852(3) 0.6167(3) 0.3196(3) 0.0290(6) Uani 1 1 d . . . . .
N8 N 0.9465(3) 0.5854(3) 0.6139(3) 0.0309(7) Uani 1 1 d . . . . .
N1 N 0.1835(4) 0.9265(3) 0.1383(3) 0.0339(7) Uani 1 1 d . . . . .
N7 N 0.7214(4) 0.6028(4) 0.5108(3) 0.0346(7) Uani 1 1 d . . . . .
N6 N 0.8193(3) 0.3590(3) 0.6584(3) 0.0298(7) Uani 1 1 d . . . . .
N4 N 0.0576(3) 0.3882(3) 0.3703(3) 0.0310(7) Uani 1 1 d . . . . .
N3 N 0.2826(3) 0.3753(3) 0.4730(3) 0.0337(7) Uani 1 1 d . . . . .
C20 C 0.8323(4) 0.5175(4) 0.5950(3) 0.0286(7) Uani 1 1 d . . . . .
C22 C 1.0581(4) 0.5045(4) 0.7112(4) 0.0298(7) Uani 1 1 d . . . . .
N5 N 0.8761(4) 0.0479(4) 0.7684(4) 0.0414(7) Uani 1 1 d . . . . .
C6 C 0.2887(4) 0.6982(4) 0.3478(4) 0.0293(7) Uani 1 1 d . . . . .
C19 C 0.7098(4) 0.2791(4) 0.6339(4) 0.0284(7) Uani 1 1 d . . . . .
C2 C 0.1162(4) 1.0781(4) 0.1231(4) 0.0386(8) Uani 1 1 d . . . . .
H2A H 0.0458 1.1159 0.0410 0.046 Uiso 1 1 calc R U . . .
H2B H 0.1895 1.1521 0.1067 0.046 Uiso 1 1 calc R U . . .
C26 C 1.2097(5) 0.5344(5) 0.9688(4) 0.0382(8) Uani 1 1 d . . . . .
H26A H 1.1485 0.6239 0.9621 0.057 Uiso 1 1 calc R U . . .
H26B H 1.2854 0.5167 1.0425 0.057 Uiso 1 1 calc R U . . .
H26C H 1.1522 0.4467 0.9966 0.057 Uiso 1 1 calc R U . . .
C12 C -0.3758(4) 0.5473(5) 0.1691(4) 0.0374(8) Uani 1 1 d . . . . .
H12A H -0.4156 0.5262 0.2660 0.056 Uiso 1 1 calc R U . . .
H12B H -0.4539 0.5659 0.0977 0.056 Uiso 1 1 calc R U . . .
H12C H -0.3205 0.6365 0.1425 0.056 Uiso 1 1 calc R U . . .
C11 C -0.3605(4) 0.2660(5) 0.2234(4) 0.0395(9) Uani 1 1 d . . . . .
H11A H -0.2972 0.1799 0.2245 0.059 Uiso 1 1 calc R U . . .
H11B H -0.4420 0.2794 0.1570 0.059 Uiso 1 1 calc R U . . .
H11C H -0.3952 0.2475 0.3218 0.059 Uiso 1 1 calc R U . . .
C5 C 0.2527(4) 0.8713(4) 0.2853(4) 0.0326(8) Uani 1 1 d . . . . .
H5 H 0.3422 0.9239 0.2810 0.039 Uiso 1 1 calc R U . . .
C10 C -0.2772(4) 0.4102(4) 0.1708(4) 0.0333(8) Uani 1 1 d . . . . .
C9 C -0.0550(4) 0.4690(4) 0.2763(4) 0.0306(8) Uani 1 1 d . . . . .
C23 C 1.2781(4) 0.5597(4) 0.8186(4) 0.0314(8) Uani 1 1 d . . . . .
C3 C 0.0422(5) 1.0501(4) 0.2694(4) 0.0419(9) Uani 1 1 d . . . . .
H3A H -0.0560 1.0191 0.2667 0.050 Uiso 1 1 calc R U . . .
H3B H 0.0379 1.1416 0.2937 0.050 Uiso 1 1 calc R U . . .
C7 C 0.1718(4) 0.4575(4) 0.3867(4) 0.0307(8) Uani 1 1 d . . . . .
C21 C 0.7272(5) 0.7677(4) 0.4313(5) 0.0454(10) Uani 1 1 d . . . . .
H21A H 0.7432 0.8161 0.5010 0.068 Uiso 1 1 calc R U . . .
H21B H 0.6365 0.8092 0.3782 0.068 Uiso 1 1 calc R U . . .
H21C H 0.8056 0.7866 0.3623 0.068 Uiso 1 1 calc R U . . .
C1 C 0.2858(6) 0.9322(5) 0.0231(5) 0.0543(12) Uani 1 1 d . . . . .
H1A H 0.3594 1.0008 0.0212 0.082 Uiso 1 1 calc R U . . .
H1B H 0.2352 0.9684 -0.0714 0.082 Uiso 1 1 calc R U . . .
H1C H 0.3310 0.8311 0.0429 0.082 Uiso 1 1 calc R U . . .
C25 C 1.3747(4) 0.4202(4) 0.8199(4) 0.0357(8) Uani 1 1 d . . . . .
H25A H 1.3187 0.3312 0.8505 0.054 Uiso 1 1 calc R U . . .
H25B H 1.4555 0.4026 0.8881 0.054 Uiso 1 1 calc R U . . .
H25C H 1.4106 0.4390 0.7219 0.054 Uiso 1 1 calc R U . . .
C18 C 0.7298(4) 0.1057(4) 0.7128(4) 0.0340(8) Uani 1 1 d . . . . .
H18 H 0.7007 0.0567 0.6448 0.041 Uiso 1 1 calc R U . . .
C13 C -0.2104(4) 0.4379(5) 0.0195(4) 0.0368(8) Uani 1 1 d . . . . .
H13A H -0.1561 0.5280 -0.0094 0.055 Uiso 1 1 calc R U . . .
H13B H -0.2867 0.4526 -0.0528 0.055 Uiso 1 1 calc R U . . .
H13C H -0.1464 0.3506 0.0254 0.055 Uiso 1 1 calc R U . . .
C14 C 0.9594(5) -0.0023(5) 0.6653(5) 0.0473(9) Uani 1 1 d . . . . .
H14A H 0.9144 -0.0862 0.6528 0.071 Uiso 1 1 calc R U . . .
H14B H 1.0571 -0.0353 0.7038 0.071 Uiso 1 1 calc R U . . .
H14C H 0.9618 0.0815 0.5710 0.071 Uiso 1 1 calc R U . . .
C24 C 1.3646(4) 0.7021(4) 0.7653(4) 0.0358(8) Uani 1 1 d . . . . .
H24A H 1.4037 0.7159 0.6694 0.054 Uiso 1 1 calc R U . . .
H24B H 1.4432 0.6897 0.8347 0.054 Uiso 1 1 calc R U . . .
H24C H 1.3017 0.7906 0.7582 0.054 Uiso 1 1 calc R U . . .
C4 C 0.1406(4) 0.9183(4) 0.3831(4) 0.0376(8) Uani 1 1 d . . . . .
H4A H 0.1889 0.9541 0.4518 0.045 Uiso 1 1 calc R U . . .
H4B H 0.0840 0.8326 0.4393 0.045 Uiso 1 1 calc R U . . .
C8 C 0.2779(5) 0.2119(4) 0.5587(5) 0.0470(11) Uani 1 1 d . . . . .
H8A H 0.2056 0.1964 0.6340 0.070 Uiso 1 1 calc R U . . .
H8B H 0.3717 0.1711 0.6050 0.070 Uiso 1 1 calc R U . . .
H8C H 0.2532 0.1603 0.4940 0.070 Uiso 1 1 calc R U . . .
C16 C 0.7393(6) -0.0095(6) 0.9825(5) 0.0523(11) Uani 1 1 d . . . . .
H16A H 0.6991 -0.0891 1.0667 0.063 Uiso 1 1 calc R U . . .
H16B H 0.7707 0.0707 1.0136 0.063 Uiso 1 1 calc R U . . .
C15 C 0.8658(5) -0.0762(5) 0.9126(5) 0.0466(10) Uani 1 1 d . . . . .
H15A H 0.9557 -0.0947 0.9707 0.056 Uiso 1 1 calc R U . . .
H15B H 0.8417 -0.1708 0.9022 0.056 Uiso 1 1 calc R U . . .
C17 C 0.6300(5) 0.0549(5) 0.8521(5) 0.0503(10) Uani 1 1 d . . . . .
H17A H 0.5702 0.1419 0.8575 0.060 Uiso 1 1 calc R U . . .
H17B H 0.5670 -0.0232 0.8499 0.060 Uiso 1 1 calc R U . . .
H7 H 0.660(5) 0.563(4) 0.497(4) 0.017(9) Uiso 1 1 d . . . . .
H3 H 0.354(5) 0.431(5) 0.489(4) 0.024(9) Uiso 1 1 d . . . . .
H6 H 0.891(6) 0.311(6) 0.705(5) 0.038(11) Uiso 1 1 d . . . . .
H2 H 0.107(7) 0.674(8) 0.252(8) 0.077(19) 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
O6 C22 1.339(4) . ?
O6 C23 1.469(4) . ?
O1 C6 1.228(4) . ?
O2 C9 1.232(4) . ?
O3 C9 1.356(4) . ?
O3 C10 1.474(4) . ?
O4 C19 1.222(4) . ?
O5 C22 1.233(4) . ?
N2 C6 1.349(5) . ?
N2 C7 1.404(4) . ?
N2 H2 0.96(7) . ?
N8 C20 1.311(5) . ?
N8 C22 1.375(4) . ?
N1 C1 1.443(5) . ?
N1 C5 1.455(4) . ?
N1 C2 1.469(4) . ?
N7 C20 1.326(5) . ?
N7 C21 1.455(5) . ?
N7 H7 0.73(4) . ?
N6 C19 1.367(5) . ?
N6 C20 1.396(5) . ?
N6 H6 0.81(6) . ?
N4 C7 1.311(5) . ?
N4 C9 1.366(4) . ?
N3 C7 1.325(5) . ?
N3 C8 1.451(5) . ?
N3 H3 0.92(4) . ?
N5 C18 1.443(5) . ?
N5 C14 1.448(5) . ?
N5 C15 1.457(5) . ?
C6 C5 1.521(4) . ?
C19 C18 1.518(5) . ?
C2 C3 1.509(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C26 C23 1.524(5) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C12 C10 1.518(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C11 C10 1.517(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C5 C4 1.547(5) . ?
C5 H5 0.9800 . ?
C10 C13 1.523(5) . ?
C23 C24 1.520(5) . ?
C23 C25 1.528(5) . ?
C3 C4 1.552(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C18 C17 1.567(6) . ?
C18 H18 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C16 C17 1.528(6) . ?
C16 C15 1.552(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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
C22 O6 C23 121.2(3) . . ?
C9 O3 C10 121.6(3) . . ?
C6 N2 C7 127.3(3) . . ?
C6 N2 H2 117(4) . . ?
C7 N2 H2 116(4) . . ?
C20 N8 C22 121.1(3) . . ?
C1 N1 C5 112.5(3) . . ?
C1 N1 C2 113.4(3) . . ?
C5 N1 C2 103.0(3) . . ?
C20 N7 C21 121.8(4) . . ?
C20 N7 H7 118(3) . . ?
C21 N7 H7 120(3) . . ?
C19 N6 C20 127.2(3) . . ?
C19 N6 H6 118(3) . . ?
C20 N6 H6 114(4) . . ?
C7 N4 C9 120.5(3) . . ?
C7 N3 C8 122.1(3) . . ?
C7 N3 H3 115(3) . . ?
C8 N3 H3 121(3) . . ?
N8 C20 N7 118.8(3) . . ?
N8 C20 N6 124.0(3) . . ?
N7 C20 N6 117.2(3) . . ?
O5 C22 O6 123.7(3) . . ?
O5 C22 N8 128.1(3) . . ?
O6 C22 N8 108.2(3) . . ?
C18 N5 C14 111.9(3) . . ?
C18 N5 C15 108.0(3) . . ?
C14 N5 C15 111.8(3) . . ?
O1 C6 N2 125.0(3) . . ?
O1 C6 C5 120.8(3) . . ?
N2 C6 C5 114.2(3) . . ?
O4 C19 N6 124.4(3) . . ?
O4 C19 C18 120.3(3) . . ?
N6 C19 C18 115.2(3) . . ?
N1 C2 C3 104.2(3) . . ?
N1 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
N1 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C5 C6 112.9(3) . . ?
N1 C5 C4 104.6(3) . . ?
C6 C5 C4 110.8(3) . . ?
N1 C5 H5 109.5 . . ?
C6 C5 H5 109.5 . . ?
C4 C5 H5 109.5 . . ?
O3 C10 C11 102.2(3) . . ?
O3 C10 C12 111.8(3) . . ?
C11 C10 C12 110.1(3) . . ?
O3 C10 C13 109.4(3) . . ?
C11 C10 C13 111.4(3) . . ?
C12 C10 C13 111.7(3) . . ?
O2 C9 O3 122.6(3) . . ?
O2 C9 N4 129.3(3) . . ?
O3 C9 N4 108.1(3) . . ?
O6 C23 C24 102.0(3) . . ?
O6 C23 C26 108.6(3) . . ?
C24 C23 C26 111.8(3) . . ?
O6 C23 C25 111.7(3) . . ?
C24 C23 C25 109.8(3) . . ?
C26 C23 C25 112.4(3) . . ?
C2 C3 C4 103.8(3) . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
C4 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
N4 C7 N3 119.3(3) . . ?
N4 C7 N2 124.2(3) . . ?
N3 C7 N2 116.4(3) . . ?
N7 C21 H21A 109.5 . . ?
N7 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N7 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N5 C18 C19 114.6(3) . . ?
N5 C18 C17 105.8(3) . . ?
C19 C18 C17 109.1(3) . . ?
N5 C18 H18 109.0 . . ?
C19 C18 H18 109.0 . . ?
C17 C18 H18 109.0 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N5 C14 H14A 109.5 . . ?
N5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C5 C4 C3 103.9(3) . . ?
C5 C4 H4A 111.0 . . ?
C3 C4 H4A 111.0 . . ?
C5 C4 H4B 111.0 . . ?
C3 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C17 C16 C15 101.3(3) . . ?
C17 C16 H16A 111.5 . . ?
C15 C16 H16A 111.5 . . ?
C17 C16 H16B 111.5 . . ?
C15 C16 H16B 111.5 . . ?
H16A C16 H16B 109.3 . . ?
N5 C15 C16 101.2(3) . . ?
N5 C15 H15A 111.5 . . ?
C16 C15 H15A 111.5 . . ?
N5 C15 H15B 111.5 . . ?
C16 C15 H15B 111.5 . . ?
H15A C15 H15B 109.4 . . ?
C16 C17 C18 103.3(3) . . ?
C16 C17 H17A 111.1 . . ?
C18 C17 H17A 111.1 . . ?
C16 C17 H17B 111.1 . . ?
C18 C17 H17B 111.1 . . ?
H17A C17 H17B 109.1 . . ?

_refine_diff_density_max         0.722
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_2016ncs0749
_database_code_depnum_ccdc_archive 'CCDC 1952638'
loop_
_audit_author_name
_audit_author_address
'Jeppe Christensen '
;national crystallography service (southampton) and diamond light source (didcot)
United Kingdom
;
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 N4 O'
_chemical_formula_sum            'C19 H20 N4 O'
_chemical_formula_weight         320.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           'P 65'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'

_cell_length_a                   9.8466(4)
_cell_length_b                   9.8466(4)
_cell_length_c                   29.7164(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2495.2(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2768
_cell_measurement_theta_max      23.86
_cell_measurement_theta_min      2.31

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             1020
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.018
_exptl_crystal_size_min          0.018
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_T_min  0.997
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CCP4 7.0.025: AIMLESS, version 0.5.29 : 17/10/16
Scaling & analysis of unmerged intensities, 
absorption correction using spherical harmonics
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_dtime           0.004
_diffrn_detector_type            'Dectris, PILATUS 2M'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_details 
;
custom build fixed Chi diffractometer, Chi=54
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_radiation_collimation    'focusing mirrors and 0.0100 mm pinhole'
_diffrn_radiation_monochromator  'Si 111, double crystal monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_source_type              'DLS beamline I19, undulator'
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_wavelength_determination estimated
_diffrn_radiation_wavelength_details 'Zr absorption edge'

_diffrn_reflns_number            25029
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_av_R_equivalents  0.1031
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.315
_diffrn_reflns_theta_max         26.563
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             3740
_reflns_number_gt                2275
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.932
_reflns_Friedel_fraction_max     0.966
_reflns_Friedel_fraction_full    0.965

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'GDA http://www.opengda.org/OpenGDA.html'
_computing_cell_refinement       
'XIA2 0.4.0.438-g4431aaa, Winter, G. (2010) J. Appl. Cryst. 43'
_computing_data_reduction        
'XIA2 0.4.0.438-g4431aaa, Winter, G. (2010) J. Appl. Cryst. 43'
_computing_structure_solution    'SHELXT Acta Cryst. (2015). A71, 3-8'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1115P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 793 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3740
_refine_ls_number_parameters     221
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0650
_refine_ls_wR_factor_ref         0.1916
_refine_ls_wR_factor_gt          0.1651
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.972
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8405(4) 0.8240(4) 0.62769(10) 0.0691(10) Uani 1 1 d . . . . .
N4 N 1.0036(5) 1.1145(4) 0.51583(11) 0.0537(9) Uani 1 1 d . . . . .
N2 N 0.8955(5) 0.8681(5) 0.55290(13) 0.0561(10) Uani 1 1 d . . . . .
N3 N 1.0437(5) 1.1186(5) 0.59046(12) 0.0541(9) Uani 1 1 d . . . . .
N1 N 0.7032(5) 0.5681(5) 0.53034(13) 0.0613(10) Uani 1 1 d . . . . .
C13 C 0.9812(5) 1.0317(6) 0.55292(15) 0.0535(10) Uani 1 1 d . . . . .
C19 C 1.0878(5) 1.2700(5) 0.53056(14) 0.0528(10) Uani 1 1 d . . . . .
C18 C 1.1397(7) 1.4092(6) 0.50677(16) 0.0619(12) Uani 1 1 d . . . . .
H18 H 1.1235 1.4093 0.4753 0.074 Uiso 1 1 calc R U . . .
C14 C 1.1126(5) 1.2740(5) 0.57702(13) 0.0524(10) Uani 1 1 d . . . . .
C12 C 0.8244(5) 0.7762(6) 0.58921(15) 0.0566(11) Uani 1 1 d . . . . .
C16 C 1.2423(6) 1.5512(6) 0.57663(16) 0.0654(13) Uani 1 1 d . . . . .
H16 H 1.2963 1.6496 0.5915 0.078 Uiso 1 1 calc R U . . .
C15 C 1.1914(5) 1.4138(5) 0.60130(16) 0.0578(11) Uani 1 1 d . . . . .
H15 H 1.2091 1.4151 0.6328 0.069 Uiso 1 1 calc R U . . .
C17 C 1.2158(7) 1.5467(6) 0.53091(16) 0.0688(14) Uani 1 1 d . . . . .
H17 H 1.2516 1.6431 0.5154 0.083 Uiso 1 1 calc R U . . .
C3 C 0.4703(7) 0.4818(8) 0.3726(2) 0.0816(16) Uani 1 1 d . . . . .
H3 H 0.4522 0.4787 0.3412 0.098 Uiso 1 1 calc R U . . .
C5 C 0.3994(7) 0.3636(7) 0.4459(2) 0.0788(16) Uani 1 1 d . . . . .
H5 H 0.3324 0.2759 0.4640 0.095 Uiso 1 1 calc R U . . .
C11 C 0.7270(7) 0.6008(7) 0.57850(17) 0.0686(13) Uani 1 1 d . . . . .
H11 H 0.6204 0.5661 0.5911 0.082 Uiso 1 1 calc R U . A 1
C4 C 0.3746(7) 0.3570(8) 0.3991(2) 0.0797(16) Uani 1 1 d . . . . .
H4 H 0.2909 0.2653 0.3860 0.096 Uiso 1 1 calc R U . . .
C8 C 0.7621(7) 0.4604(7) 0.51948(18) 0.0766(15) Uani 1 1 d D . . . .
H8A H 0.8157 0.4855 0.4899 0.092 Uiso 1 1 calc R U . B 1
H8B H 0.6765 0.3497 0.5196 0.092 Uiso 1 1 calc R U . B 1
C1 C 0.6161(8) 0.6184(8) 0.4380(2) 0.094(2) Uani 1 1 d . . . . .
H1 H 0.7007 0.7101 0.4508 0.112 Uiso 1 1 calc R U . . .
C7 C 0.5403(7) 0.5091(9) 0.5160(2) 0.0854(18) Uani 1 1 d . . . . .
H7A H 0.5043 0.5800 0.5276 0.102 Uiso 1 1 calc R U . . .
H7B H 0.4729 0.4043 0.5294 0.102 Uiso 1 1 calc R U . . .
C6 C 0.5206(7) 0.4967(8) 0.4658(2) 0.0758(15) Uani 1 1 d . . . . .
C2 C 0.5940(8) 0.6128(8) 0.3921(2) 0.097(2) Uani 1 1 d . . . . .
H2 H 0.6637 0.6989 0.3738 0.116 Uiso 1 1 calc R U . . .
C10A C 0.8565(15) 0.5449(13) 0.5952(4) 0.0602(17) Uiso 0.454(7) 1 d D . P C 2
H10A H 0.9653 0.6207 0.5860 0.072 Uiso 0.454(7) 1 calc R U P C 2
H10B H 0.8523 0.5262 0.6281 0.072 Uiso 0.454(7) 1 calc R U P C 2
C9 C 0.8733(11) 0.4926(12) 0.5568(3) 0.0675(18) Uiso 0.546(7) 1 d D . P C 1
H9A H 0.9702 0.5956 0.5534 0.081 Uiso 0.546(7) 1 calc R U P C 1
H9B H 0.9006 0.4091 0.5600 0.081 Uiso 0.546(7) 1 calc R U P C 1
C9A C 0.7878(15) 0.3952(14) 0.5685(4) 0.0675(18) Uiso 0.454(7) 1 d D . P C 2
H9A1 H 0.6874 0.3130 0.5815 0.081 Uiso 0.454(7) 1 calc R U P C 2
H9A2 H 0.8616 0.3548 0.5660 0.081 Uiso 0.454(7) 1 calc R U P C 2
C10 C 0.7702(12) 0.4920(12) 0.5958(3) 0.0602(17) Uiso 0.546(7) 1 d D . P C 1
H10C H 0.6776 0.3868 0.6005 0.072 Uiso 0.546(7) 1 calc R U P C 1
H10D H 0.8301 0.5296 0.6242 0.072 Uiso 0.546(7) 1 calc R U P C 1
H19 H 1.042(6) 1.087(6) 0.618(2) 0.072 Uiso 1 1 d . U . . .
H20 H 0.893(6) 0.833(6) 0.526(2) 0.072 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.217(5) . ?
N4 C13 1.322(6) . ?
N4 C19 1.398(6) . ?
N2 C12 1.356(6) . ?
N2 C13 1.395(6) . ?
N2 H20 0.88(6) . ?
N3 C13 1.353(6) . ?
N3 C14 1.386(6) . ?
N3 H19 0.88(6) . ?
N1 C11 1.460(6) . ?
N1 C7 1.470(7) . ?
N1 C8 1.477(7) . ?
C19 C18 1.392(6) . ?
C19 C14 1.399(5) . ?
C18 C17 1.377(7) . ?
C18 H18 0.9500 . ?
C14 C15 1.396(6) . ?
C12 C11 1.533(8) . ?
C16 C17 1.380(6) . ?
C16 C15 1.393(7) . ?
C16 H16 0.9500 . ?
C15 H15 0.9500 . ?
C17 H17 0.9500 . ?
C3 C4 1.364(9) . ?
C3 C2 1.381(9) . ?
C3 H3 0.9500 . ?
C5 C6 1.389(9) . ?
C5 C4 1.406(9) . ?
C5 H5 0.9500 . ?
C11 C10 1.430(10) . ?
C11 C10A 1.696(13) . ?
C11 H11 1.0000 . ?
C4 H4 0.9500 . ?
C8 C9 1.476(10) . ?
C8 C9A 1.663(11) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C1 C6 1.370(9) . ?
C1 C2 1.378(9) . ?
C1 H1 0.9500 . ?
C7 C6 1.500(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C2 H2 0.9500 . ?
C10A C9A 1.504(14) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C9 C10 1.539(12) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
C10 H10C 0.9900 . ?
C10 H10D 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N4 C19 103.9(3) . . ?
C12 N2 C13 125.6(4) . . ?
C12 N2 H20 125(4) . . ?
C13 N2 H20 110(4) . . ?
C13 N3 C14 106.1(4) . . ?
C13 N3 H19 129(4) . . ?
C14 N3 H19 125(4) . . ?
C11 N1 C7 113.3(4) . . ?
C11 N1 C8 107.1(4) . . ?
C7 N1 C8 113.3(4) . . ?
N4 C13 N3 114.5(4) . . ?
N4 C13 N2 122.0(4) . . ?
N3 C13 N2 123.5(4) . . ?
C18 C19 N4 130.1(4) . . ?
C18 C19 C14 120.0(4) . . ?
N4 C19 C14 109.8(4) . . ?
C17 C18 C19 117.1(4) . . ?
C17 C18 H18 121.5 . . ?
C19 C18 H18 121.5 . . ?
N3 C14 C15 131.5(4) . . ?
N3 C14 C19 105.7(4) . . ?
C15 C14 C19 122.7(4) . . ?
O1 C12 N2 124.5(5) . . ?
O1 C12 C11 121.2(4) . . ?
N2 C12 C11 114.2(4) . . ?
C17 C16 C15 121.1(5) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C15 C14 116.0(4) . . ?
C16 C15 H15 122.0 . . ?
C14 C15 H15 122.0 . . ?
C18 C17 C16 123.1(5) . . ?
C18 C17 H17 118.5 . . ?
C16 C17 H17 118.5 . . ?
C4 C3 C2 119.3(6) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C6 C5 C4 120.9(6) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C10 C11 N1 105.2(6) . . ?
C10 C11 C12 121.1(6) . . ?
N1 C11 C12 113.1(4) . . ?
N1 C11 C10A 106.3(5) . . ?
C12 C11 C10A 99.0(6) . . ?
C10 C11 H11 105.4 . . ?
N1 C11 H11 105.4 . . ?
C12 C11 H11 105.4 . . ?
C3 C4 C5 120.1(6) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N1 C8 C9 101.4(5) . . ?
N1 C8 C9A 106.0(5) . . ?
N1 C8 H8A 111.5 . . ?
C9 C8 H8A 111.5 . . ?
N1 C8 H8B 111.5 . . ?
C9 C8 H8B 111.5 . . ?
H8A C8 H8B 109.3 . . ?
C6 C1 C2 122.5(6) . . ?
C6 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
N1 C7 C6 113.1(4) . . ?
N1 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C1 C6 C5 117.2(6) . . ?
C1 C6 C7 121.7(6) . . ?
C5 C6 C7 121.1(5) . . ?
C1 C2 C3 119.9(6) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C9A C10A C11 97.0(8) . . ?
C9A C10A H10A 112.4 . . ?
C11 C10A H10A 112.4 . . ?
C9A C10A H10B 112.4 . . ?
C11 C10A H10B 112.4 . . ?
H10A C10A H10B 109.9 . . ?
C8 C9 C10 98.5(7) . . ?
C8 C9 H9A 112.1 . . ?
C10 C9 H9A 112.1 . . ?
C8 C9 H9B 112.1 . . ?
C10 C9 H9B 112.1 . . ?
H9A C9 H9B 109.7 . . ?
C10A C9A C8 99.4(8) . . ?
C10A C9A H9A1 111.9 . . ?
C8 C9A H9A1 111.9 . . ?
C10A C9A H9A2 111.9 . . ?
C8 C9A H9A2 111.9 . . ?
H9A1 C9A H9A2 109.6 . . ?
C11 C10 C9 99.8(7) . . ?
C11 C10 H10C 111.8 . . ?
C9 C10 H10C 111.8 . . ?
C11 C10 H10D 111.8 . . ?
C9 C10 H10D 111.8 . . ?
H10C C10 H10D 109.5 . . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.051

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

data_shelx_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 1952645'
loop_
_audit_author_name
_audit_author_address
'Jeppe Christensen '
;national crystallography service (southampton) and diamond light source (didcot)
United Kingdom
;
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H21 N3 O3'
_chemical_formula_sum            'C11 H21 N3 O3'
_chemical_formula_weight         243.31

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   9.7621(4)
_cell_length_b                   13.2127(4)
_cell_length_c                   21.9038(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2825.23(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4209
_cell_measurement_theta_min      4.5200
_cell_measurement_theta_max      66.0310

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.021
_exptl_absorpt_coefficient_mu    0.689
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC11 quarter χ goniometer'
_diffrn_measurement_device_type  
;
Rigaku 007HF equipped with Varimax confocal mirrors 
and an AFC11 goniometer and HyPix 6000 detector
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_radiation_collimation    'Varimax focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'Rotating anode'
_diffrn_source_type              'Rigaku 007 HF'
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_source_current           30.0
_diffrn_source_target            Cu
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0287645000
_diffrn_orient_matrix_UB_12      0.1089185000
_diffrn_orient_matrix_UB_13      -0.0216691000
_diffrn_orient_matrix_UB_21      0.1540010000
_diffrn_orient_matrix_UB_22      -0.0245435000
_diffrn_orient_matrix_UB_23      -0.0042684000
_diffrn_orient_matrix_UB_31      -0.0192375000
_diffrn_orient_matrix_UB_32      -0.0336916000
_diffrn_orient_matrix_UB_33      -0.0667453000
_diffrn_measurement_details      
;Data collection strategy using shutter-less operation of detector.
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00   6.00   0.50    2.00    --    5.00  19.00 -78.00   50
  2  ω    -22.00  81.00   0.50    2.00    --    0.00  60.00-180.00  206
  3  ω   -179.00  -3.00   0.50   10.00    --  -90.00  60.00   0.00  352
  4  ω    -46.00 -20.00   0.50   10.00    --  -90.00  60.00  60.00   52
  5  ω   -178.00 -66.00   0.50   10.00    --  -90.00  60.00  60.00  224
  6  ω    -73.00  -1.00   0.50   10.00    --  -90.00  60.00  30.00  144
  7  ω   -160.00-134.00   0.50   10.00    --  -90.00  60.00 150.00   52
  8  ω   -111.00 -85.00   0.50   10.00    --  -90.00  60.00 150.00   52
  9  ω    -46.00  -2.00   0.50   10.00    --  -90.00  60.00 150.00   88
 10  ω   -159.00-133.00   0.50   10.00    --  -90.00  60.00  90.00   52
 11  ω   -177.00-151.00   0.50   10.00    --  -90.00  60.00  30.00   52
 12  ω    -58.00  -1.00   0.50   10.00    --  -90.00  57.00 -60.00  114
 13  ω   -173.00-147.00   0.50   10.00    --  -90.00  57.00 -60.00   52
 14  ω   -136.00 -82.00   0.50   10.00    --  -90.00  57.00 -60.00  108
 15  ω   -111.00 -85.00   0.50   10.00    --  -90.00  19.00 -78.00   52
 16  ω   -154.00  -2.00   0.50   10.00    --  -90.00   0.00  60.00  304 
;
_diffrn_reflns_number            21112
_diffrn_reflns_av_unetI/netI     0.0994
_diffrn_reflns_av_R_equivalents  0.1546
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.907
_diffrn_reflns_theta_max         70.413
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_point_group_measured_fraction_full 0.875
_reflns_number_total             4634
_reflns_number_gt                3726
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_max     0.723
_reflns_Friedel_fraction_full    0.744

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_structure_solution    SHELXT-2018
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 991 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4634
_refine_ls_number_parameters     280
_refine_ls_number_restraints     69
_refine_ls_R_factor_all          0.1517
_refine_ls_R_factor_gt           0.1390
_refine_ls_wR_factor_ref         0.3834
_refine_ls_wR_factor_gt          0.3735
_refine_ls_goodness_of_fit_ref   1.477
_refine_ls_restrained_S_all      1.488
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.4843(6) 0.7000(5) 0.4177(3) 0.0474(16) Uani 1 1 d . . . . .
N5 N 0.7124(6) 0.7258(5) 0.4241(4) 0.0372(16) Uani 1 1 d . . . . .
H5 H 0.7810 0.7652 0.4175 0.045 Uiso 1 1 calc R U . . .
C17 C 0.5888(7) 0.7560(6) 0.4082(4) 0.0330(16) Uani 1 1 d . . . . .
O3 O 0.4054(8) 0.4494(5) 0.5279(4) 0.0556(19) Uani 1 1 d . . . . .
O6 O 0.7271(8) 0.5546(5) 0.3594(4) 0.0531(17) Uani 1 1 d . . . . .
O5 O 0.7267(8) 0.4667(4) 0.4486(4) 0.0556(18) Uani 1 1 d . . . . .
O1 O 0.6424(7) 0.6949(6) 0.5691(3) 0.0522(17) Uani 1 1 d . . . . .
N3 N 0.3965(7) 0.6176(5) 0.5326(3) 0.0392(17) Uani 1 1 d . . . . .
H3 H 0.3852 0.6223 0.4937 0.047 Uiso 1 1 calc R U . . .
N6 N 0.7354(7) 0.6321(5) 0.4511(4) 0.0422(17) Uani 1 1 d . . . . .
H6 H 0.7541 0.6262 0.4893 0.051 Uiso 1 1 calc R U . . .
O2 O 0.3978(7) 0.5307(5) 0.6198(3) 0.0526(18) Uani 1 1 d . . . . .
N2 N 0.4118(8) 0.7043(6) 0.5665(4) 0.0431(18) Uani 1 1 d . . . . .
H2 H 0.3403 0.7380 0.5770 0.052 Uiso 1 1 calc R U . . .
C7 C 0.3989(9) 0.5237(7) 0.5591(4) 0.0385(19) Uani 1 1 d . . . . .
C18 C 0.7264(9) 0.5481(6) 0.4127(5) 0.045(2) Uani 1 1 d . . . . .
C16A C 0.579(3) 0.851(3) 0.3760(12) 0.0462(17) Uiso 0.547(10) 1 d D . P A 1
H16A H 0.5009 0.8916 0.3895 0.055 Uiso 0.547(10) 1 calc R U P A 1
C6 C 0.5364(8) 0.7377(7) 0.5836(4) 0.0415(19) Uani 1 1 d . . . . .
C5B C 0.541(2) 0.8309(18) 0.6222(10) 0.0462(17) Uiso 0.550(11) 1 d D . P B 1
H5B H 0.6139 0.8756 0.6070 0.055 Uiso 0.550(11) 1 calc R U P B 1
C3B C 0.430(2) 0.8199(19) 0.7178(13) 0.076(4) Uiso 0.550(11) 1 d D . P B 1
H3B1 H 0.4313 0.8296 0.7617 0.091 Uiso 0.550(11) 1 calc R U P B 1
H3B2 H 0.3674 0.7651 0.7081 0.091 Uiso 0.550(11) 1 calc R U P B 1
C8 C 0.3963(12) 0.4385(8) 0.6569(5) 0.056(3) Uani 1 1 d . . . . .
C2A C 0.397(4) 0.962(3) 0.676(2) 0.085(10) Uiso 0.450(11) 1 d . . P B 2
H2A1 H 0.3097 0.9745 0.6964 0.103 Uiso 0.450(11) 1 calc R U P B 2
H2A2 H 0.4713 0.9922 0.6993 0.103 Uiso 0.450(11) 1 calc R U P B 2
C11 C 0.2654(14) 0.3778(11) 0.6441(8) 0.088(5) Uani 1 1 d . . . . .
H11A H 0.2652 0.3175 0.6686 0.131 Uiso 1 1 calc R U . . .
H11B H 0.1868 0.4182 0.6540 0.131 Uiso 1 1 calc R U . . .
H11C H 0.2624 0.3597 0.6017 0.131 Uiso 1 1 calc R U . . .
N4A N 0.7008(14) 0.9056(10) 0.3769(6) 0.0469(18) Uiso 0.547(10) 1 d D . P A 1
C19 C 0.7114(13) 0.3661(8) 0.4210(7) 0.071(3) Uani 1 1 d . . . . .
C9 C 0.5236(12) 0.3777(11) 0.6475(8) 0.079(4) Uani 1 1 d . . . . .
H9A H 0.5200 0.3179 0.6723 0.118 Uiso 1 1 calc R U . . .
H9B H 0.5307 0.3588 0.6053 0.118 Uiso 1 1 calc R U . . .
H9C H 0.6019 0.4174 0.6588 0.118 Uiso 1 1 calc R U . . .
C21 C 0.710(2) 0.2970(9) 0.4761(8) 0.101(6) Uani 1 1 d . . . . .
H21A H 0.7004 0.2281 0.4629 0.151 Uiso 1 1 calc R U . . .
H21B H 0.7945 0.3044 0.4982 0.151 Uiso 1 1 calc R U . . .
H21C H 0.6347 0.3147 0.5021 0.151 Uiso 1 1 calc R U . . .
C14A C 0.715(2) 0.831(2) 0.2771(12) 0.076(4) Uiso 0.547(10) 1 d D . P A 1
H14A H 0.7154 0.8470 0.2339 0.091 Uiso 0.547(10) 1 calc R U P A 1
H14B H 0.7726 0.7730 0.2853 0.091 Uiso 0.547(10) 1 calc R U P A 1
C22 C 0.5693(13) 0.3668(9) 0.3881(7) 0.071(3) Uani 1 1 d . . . . .
H22A H 0.5540 0.3023 0.3691 0.107 Uiso 1 1 calc R U . . .
H22B H 0.4983 0.3796 0.4174 0.107 Uiso 1 1 calc R U . . .
H22C H 0.5684 0.4190 0.3576 0.107 Uiso 1 1 calc R U . . .
N1B N 0.4174(13) 0.8845(10) 0.6241(6) 0.0469(18) Uiso 0.550(11) 1 d D . P B 1
C20 C 0.8193(13) 0.3466(9) 0.3749(9) 0.084(5) Uani 1 1 d . . . . .
H20A H 0.8066 0.2805 0.3577 0.127 Uiso 1 1 calc R U . . .
H20B H 0.8137 0.3965 0.3432 0.127 Uiso 1 1 calc R U . . .
H20C H 0.9077 0.3503 0.3941 0.127 Uiso 1 1 calc R U . . .
C10 C 0.3928(18) 0.4801(14) 0.7212(6) 0.087(4) Uani 1 1 d . . . . .
H10A H 0.3915 0.4252 0.7498 0.130 Uiso 1 1 calc R U . . .
H10B H 0.4725 0.5211 0.7281 0.130 Uiso 1 1 calc R U . . .
H10C H 0.3120 0.5207 0.7264 0.130 Uiso 1 1 calc R U . . .
C4B C 0.5772(19) 0.7972(16) 0.6929(8) 0.055(2) Uiso 0.550(11) 1 d D . P B 1
H4B1 H 0.6021 0.7263 0.6964 0.066 Uiso 0.550(11) 1 calc R U P B 1
H4B2 H 0.6469 0.8394 0.7115 0.066 Uiso 0.550(11) 1 calc R U P B 1
C15A C 0.5686(19) 0.8206(16) 0.3038(8) 0.055(2) Uiso 0.547(10) 1 d D . P A 1
H15A H 0.5363 0.7515 0.2994 0.066 Uiso 0.547(10) 1 calc R U P A 1
H15B H 0.5057 0.8654 0.2827 0.066 Uiso 0.547(10) 1 calc R U P A 1
C12A C 0.681(2) 0.9885(17) 0.4191(10) 0.064(3) Uiso 0.547(10) 1 d D . P A 1
H12A H 0.7629 1.0284 0.4211 0.096 Uiso 0.547(10) 1 calc R U P A 1
H12B H 0.6063 1.0300 0.4052 0.096 Uiso 0.547(10) 1 calc R U P A 1
H12C H 0.6599 0.9622 0.4588 0.096 Uiso 0.547(10) 1 calc R U P A 1
C13A C 0.754(2) 0.9286(17) 0.3195(9) 0.064(3) Uiso 0.547(10) 1 d D . P A 1
H13A H 0.8522 0.9379 0.3214 0.076 Uiso 0.547(10) 1 calc R U P A 1
H13B H 0.7123 0.9898 0.3034 0.076 Uiso 0.547(10) 1 calc R U P A 1
C1B C 0.407(2) 0.9689(16) 0.5815(12) 0.064(3) Uiso 0.550(11) 1 d D . P B 1
H1B1 H 0.3188 1.0008 0.5861 0.096 Uiso 0.550(11) 1 calc R U P B 1
H1B2 H 0.4776 1.0172 0.5898 0.096 Uiso 0.550(11) 1 calc R U P B 1
H1B3 H 0.4161 0.9443 0.5404 0.096 Uiso 0.550(11) 1 calc R U P B 1
C1A C 0.448(3) 0.784(2) 0.7173(12) 0.064(3) Uiso 0.450(11) 1 d D . P B 2
H1A1 H 0.3653 0.7846 0.7414 0.096 Uiso 0.450(11) 1 calc R U P B 2
H1A2 H 0.4735 0.7150 0.7092 0.096 Uiso 0.450(11) 1 calc R U P B 2
H1A3 H 0.5197 0.8171 0.7393 0.096 Uiso 0.450(11) 1 calc R U P B 2
N1A N 0.4233(17) 0.8368(12) 0.6594(8) 0.0469(18) Uiso 0.450(11) 1 d D . P B 2
C2B C 0.384(3) 0.9263(14) 0.6820(8) 0.064(3) Uiso 0.550(11) 1 d D . P B 1
H2B1 H 0.2881 0.9425 0.6865 0.076 Uiso 0.550(11) 1 calc R U P B 1
H2B2 H 0.4409 0.9840 0.6929 0.076 Uiso 0.550(11) 1 calc R U P B 1
C3A C 0.397(3) 0.987(2) 0.6154(13) 0.076(4) Uiso 0.450(11) 1 d D . P B 2
H3A1 H 0.4081 1.0602 0.6131 0.091 Uiso 0.450(11) 1 calc R U P B 2
H3A2 H 0.3065 0.9721 0.5997 0.091 Uiso 0.450(11) 1 calc R U P B 2
C4A C 0.503(2) 0.9398(16) 0.5703(10) 0.055(2) Uiso 0.450(11) 1 d D . P B 2
H4A1 H 0.5830 0.9816 0.5638 0.066 Uiso 0.450(11) 1 calc R U P B 2
H4A2 H 0.4626 0.9196 0.5316 0.066 Uiso 0.450(11) 1 calc R U P B 2
C5A C 0.530(3) 0.845(2) 0.6166(12) 0.0462(17) Uiso 0.450(11) 1 d D . P B 2
H5A H 0.6158 0.8568 0.6384 0.055 Uiso 0.450(11) 1 calc R U P B 2
C12B C 0.659(3) 0.822(2) 0.2771(12) 0.064(3) Uiso 0.453(10) 1 d D . P A 2
H12D H 0.7311 0.8302 0.2478 0.096 Uiso 0.453(10) 1 calc R U P A 2
H12E H 0.6451 0.7509 0.2848 0.096 Uiso 0.453(10) 1 calc R U P A 2
H12F H 0.5759 0.8508 0.2614 0.096 Uiso 0.453(10) 1 calc R U P A 2
N4B N 0.6963(17) 0.8724(12) 0.3339(8) 0.0469(18) Uiso 0.453(10) 1 d D . P A 2
C16B C 0.583(4) 0.853(3) 0.3704(15) 0.0462(17) Uiso 0.453(10) 1 d D . P A 2
H16B H 0.4980 0.8563 0.3465 0.055 Uiso 0.453(10) 1 calc R U P A 2
C15B C 0.594(2) 0.9496(16) 0.4181(12) 0.055(2) Uiso 0.453(10) 1 d D . P A 2
H15C H 0.5064 0.9836 0.4212 0.066 Uiso 0.453(10) 1 calc R U P A 2
H15D H 0.6201 0.9259 0.4584 0.066 Uiso 0.453(10) 1 calc R U P A 2
C14B C 0.703(3) 1.023(2) 0.3935(13) 0.076(4) Uiso 0.453(10) 1 d D . P A 2
H14C H 0.7882 1.0179 0.4158 0.091 Uiso 0.453(10) 1 calc R U P A 2
H14D H 0.6709 1.0923 0.3935 0.091 Uiso 0.453(10) 1 calc R U P A 2
C13B C 0.715(3) 0.9768(16) 0.3248(11) 0.064(3) Uiso 0.453(10) 1 d D . P A 2
H13C H 0.6445 1.0043 0.2983 0.076 Uiso 0.453(10) 1 calc R U P A 2
H13D H 0.8041 0.9909 0.3072 0.076 Uiso 0.453(10) 1 calc R U P A 2


_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
O4 C17 1.277(10) . ?
N5 C17 1.318(10) . ?
N5 N6 1.391(10) . ?
N5 H5 0.8600 . ?
C17 C16A 1.44(4) . ?
C17 C16B 1.53(5) . ?
O3 C7 1.197(12) . ?
O6 C18 1.169(13) . ?
O5 C18 1.333(12) . ?
O5 C19 1.468(12) . ?
O1 C6 1.222(11) . ?
N3 C7 1.370(11) . ?
N3 N2 1.373(11) . ?
N3 H3 0.8600 . ?
N6 C18 1.396(12) . ?
N6 H6 0.8600 . ?
O2 C7 1.333(12) . ?
O2 C8 1.466(12) . ?
N2 C6 1.347(11) . ?
N2 H2 0.8600 . ?
C16A N4A 1.388(18) . ?
C16A C15A 1.63(2) . ?
C16A H16A 0.9800 . ?
C6 C5B 1.49(3) . ?
C6 C5A 1.60(3) . ?
C5B N1B 1.403(17) . ?
C5B C4B 1.65(2) . ?
C5B H5B 0.9800 . ?
C3B C4B 1.57(2) . ?
C3B C2B 1.67(2) . ?
C3B H3B1 0.9700 . ?
C3B H3B2 0.9700 . ?
C8 C9 1.494(19) . ?
C8 C10 1.51(2) . ?
C8 C11 1.534(18) . ?
C2A C3A 1.38(5) . ?
C2A N1A 1.71(4) . ?
C2A H2A1 0.9700 . ?
C2A H2A2 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
N4A C13A 1.395(18) . ?
N4A C12A 1.445(19) . ?
C19 C20 1.48(2) . ?
C19 C21 1.51(2) . ?
C19 C22 1.56(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C14A C15A 1.55(2) . ?
C14A C13A 1.63(2) . ?
C14A H14A 0.9700 . ?
C14A H14B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N1B C2B 1.421(18) . ?
N1B C1B 1.46(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C4B H4B1 0.9700 . ?
C4B H4B2 0.9700 . ?
C15A H15A 0.9700 . ?
C15A H15B 0.9700 . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C13A H13A 0.9700 . ?
C13A H13B 0.9700 . ?
C1B H1B1 0.9600 . ?
C1B H1B2 0.9600 . ?
C1B H1B3 0.9600 . ?
C1A N1A 1.47(2) . ?
C1A H1A1 0.9600 . ?
C1A H1A2 0.9600 . ?
C1A H1A3 0.9600 . ?
N1A C5A 1.402(19) . ?
C2B H2B1 0.9700 . ?
C2B H2B2 0.9700 . ?
C3A C4A 1.56(2) . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
C4A C5A 1.63(2) . ?
C4A H4A1 0.9700 . ?
C4A H4A2 0.9700 . ?
C5A H5A 0.9800 . ?
C12B N4B 1.46(2) . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?
N4B C16B 1.390(19) . ?
N4B C13B 1.406(19) . ?
C16B C15B 1.65(2) . ?
C16B H16B 0.9800 . ?
C15B C14B 1.53(3) . ?
C15B H15C 0.9700 . ?
C15B H15D 0.9700 . ?
C14B C13B 1.63(2) . ?
C14B H14C 0.9700 . ?
C14B H14D 0.9700 . ?
C13B H13C 0.9700 . ?
C13B H13D 0.9700 . ?

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
C17 N5 N6 122.0(7) . . ?
C17 N5 H5 119.0 . . ?
N6 N5 H5 119.0 . . ?
O4 C17 N5 120.9(8) . . ?
O4 C17 C16A 122.1(12) . . ?
N5 C17 C16A 116.9(12) . . ?
O4 C17 C16B 122.9(14) . . ?
N5 C17 C16B 115.6(14) . . ?
C18 O5 C19 119.1(9) . . ?
C7 N3 N2 121.6(7) . . ?
C7 N3 H3 119.2 . . ?
N2 N3 H3 119.2 . . ?
N5 N6 C18 116.1(8) . . ?
N5 N6 H6 121.9 . . ?
C18 N6 H6 121.9 . . ?
C7 O2 C8 119.7(8) . . ?
C6 N2 N3 121.5(7) . . ?
C6 N2 H2 119.3 . . ?
N3 N2 H2 119.3 . . ?
O3 C7 O2 128.8(9) . . ?
O3 C7 N3 120.1(8) . . ?
O2 C7 N3 111.0(8) . . ?
O6 C18 O5 130.4(9) . . ?
O6 C18 N6 122.9(9) . . ?
O5 C18 N6 106.5(9) . . ?
N4A C16A C17 113(3) . . ?
N4A C16A C15A 101.4(15) . . ?
C17 C16A C15A 105(2) . . ?
N4A C16A H16A 112.2 . . ?
C17 C16A H16A 112.2 . . ?
C15A C16A H16A 112.2 . . ?
O1 C6 N2 122.8(8) . . ?
O1 C6 C5B 120.0(10) . . ?
N2 C6 C5B 117.2(10) . . ?
O1 C6 C5A 124.4(12) . . ?
N2 C6 C5A 112.3(11) . . ?
N1B C5B C6 113.8(18) . . ?
N1B C5B C4B 106.9(15) . . ?
C6 C5B C4B 108.4(15) . . ?
N1B C5B H5B 109.2 . . ?
C6 C5B H5B 109.2 . . ?
C4B C5B H5B 109.2 . . ?
C4B C3B C2B 104.0(17) . . ?
C4B C3B H3B1 111.0 . . ?
C2B C3B H3B1 111.0 . . ?
C4B C3B H3B2 111.0 . . ?
C2B C3B H3B2 111.0 . . ?
H3B1 C3B H3B2 109.0 . . ?
O2 C8 C9 111.2(9) . . ?
O2 C8 C10 102.4(10) . . ?
C9 C8 C10 110.1(11) . . ?
O2 C8 C11 110.0(9) . . ?
C9 C8 C11 112.7(11) . . ?
C10 C8 C11 110.0(12) . . ?
C3A C2A N1A 91(3) . . ?
C3A C2A H2A1 113.4 . . ?
N1A C2A H2A1 113.4 . . ?
C3A C2A H2A2 113.4 . . ?
N1A C2A H2A2 113.4 . . ?
H2A1 C2A H2A2 110.7 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C16A N4A C13A 114.6(17) . . ?
C16A N4A C12A 106.7(19) . . ?
C13A N4A C12A 117.5(16) . . ?
O5 C19 C20 111.5(9) . . ?
O5 C19 C21 102.6(11) . . ?
C20 C19 C21 116.4(12) . . ?
O5 C19 C22 106.0(9) . . ?
C20 C19 C22 108.6(13) . . ?
C21 C19 C22 111.3(12) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C15A C14A C13A 94.1(16) . . ?
C15A C14A H14A 112.9 . . ?
C13A C14A H14A 112.9 . . ?
C15A C14A H14B 112.9 . . ?
C13A C14A H14B 112.9 . . ?
H14A C14A H14B 110.3 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C5B N1B C2B 114.7(17) . . ?
C5B N1B C1B 115.4(16) . . ?
C2B N1B C1B 105.0(14) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3B C4B C5B 94.7(15) . . ?
C3B C4B H4B1 112.8 . . ?
C5B C4B H4B1 112.8 . . ?
C3B C4B H4B2 112.8 . . ?
C5B C4B H4B2 112.8 . . ?
H4B1 C4B H4B2 110.3 . . ?
C14A C15A C16A 106.4(16) . . ?
C14A C15A H15A 110.4 . . ?
C16A C15A H15A 110.4 . . ?
C14A C15A H15B 110.4 . . ?
C16A C15A H15B 110.4 . . ?
H15A C15A H15B 108.6 . . ?
N4A C12A H12A 109.5 . . ?
N4A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
N4A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
N4A C13A C14A 104.9(17) . . ?
N4A C13A H13A 110.8 . . ?
C14A C13A H13A 110.8 . . ?
N4A C13A H13B 110.8 . . ?
C14A C13A H13B 110.8 . . ?
H13A C13A H13B 108.8 . . ?
N1B C1B H1B1 109.5 . . ?
N1B C1B H1B2 109.5 . . ?
H1B1 C1B H1B2 109.5 . . ?
N1B C1B H1B3 109.5 . . ?
H1B1 C1B H1B3 109.5 . . ?
H1B2 C1B H1B3 109.5 . . ?
N1A C1A H1A1 109.5 . . ?
N1A C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 109.5 . . ?
N1A C1A H1A3 109.5 . . ?
H1A1 C1A H1A3 109.5 . . ?
H1A2 C1A H1A3 109.5 . . ?
C5A N1A C1A 119.8(19) . . ?
C5A N1A C2A 100(2) . . ?
C1A N1A C2A 107(2) . . ?
N1B C2B C3B 91.9(15) . . ?
N1B C2B H2B1 113.3 . . ?
C3B C2B H2B1 113.3 . . ?
N1B C2B H2B2 113.3 . . ?
C3B C2B H2B2 113.3 . . ?
H2B1 C2B H2B2 110.6 . . ?
C2A C3A C4A 121(3) . . ?
C2A C3A H3A1 107.0 . . ?
C4A C3A H3A1 107.0 . . ?
C2A C3A H3A2 107.0 . . ?
C4A C3A H3A2 107.0 . . ?
H3A1 C3A H3A2 106.8 . . ?
C3A C4A C5A 91.2(16) . . ?
C3A C4A H4A1 113.4 . . ?
C5A C4A H4A1 113.4 . . ?
C3A C4A H4A2 113.4 . . ?
C5A C4A H4A2 113.4 . . ?
H4A1 C4A H4A2 110.7 . . ?
N1A C5A C6 105.2(18) . . ?
N1A C5A C4A 111.0(17) . . ?
C6 C5A C4A 114(2) . . ?
N1A C5A H5A 108.8 . . ?
C6 C5A H5A 108.8 . . ?
C4A C5A H5A 108.8 . . ?
N4B C12B H12D 109.5 . . ?
N4B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
N4B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C16B N4B C13B 111(2) . . ?
C16B N4B C12B 102(2) . . ?
C13B N4B C12B 111(2) . . ?
N4B C16B C17 116(3) . . ?
N4B C16B C15B 99.7(18) . . ?
C17 C16B C15B 108(2) . . ?
N4B C16B H16B 111.0 . . ?
C17 C16B H16B 111.0 . . ?
C15B C16B H16B 111.0 . . ?
C14B C15B C16B 108.1(19) . . ?
C14B C15B H15C 110.1 . . ?
C16B C15B H15C 110.1 . . ?
C14B C15B H15D 110.1 . . ?
C16B C15B H15D 110.1 . . ?
H15C C15B H15D 108.4 . . ?
C15B C14B C13B 98(2) . . ?
C15B C14B H14C 112.2 . . ?
C13B C14B H14C 112.2 . . ?
C15B C14B H14D 112.2 . . ?
C13B C14B H14D 112.2 . . ?
H14C C14B H14D 109.8 . . ?
N4B C13B C14B 103.1(19) . . ?
N4B C13B H13C 111.2 . . ?
C14B C13B H13C 111.2 . . ?
N4B C13B H13D 111.2 . . ?
C14B C13B H13D 111.2 . . ?
H13C C13B H13D 109.1 . . ?

_refine_diff_density_max         0.548
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.101

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

data_shelx_CCDC7
_database_code_depnum_ccdc_archive 'CCDC 1952643'
loop_
_audit_author_name
_audit_author_address
'Jeppe Christensen '
;national crystallography service (southampton) and diamond light source (didcot)
United Kingdom
;
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H39 N5 O2'
_chemical_formula_sum            'C23 H39 N5 O2'
_chemical_formula_weight         417.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.0504(6)
_cell_length_b                   24.8719(7)
_cell_length_c                   10.3198(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.323(7)
_cell_angle_gamma                90
_cell_volume                     2350.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    24695
_cell_measurement_theta_min      2.8750
_cell_measurement_theta_max      29.7340

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_T_min  0.68342
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.

Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_collimation    '0.07 mm Confocal mirrors, HF Varimax'
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_source                   'rotating anode'
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source_target            Mo
_diffrn_source_type              'FR-E+ SuperBright rotating anode'
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12'
_diffrn_measurement_method       'profile data from ω scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 14.286
_diffrn_reflns_number            73118
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_av_R_equivalents  0.0833
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.716
_diffrn_reflns_theta_max         29.836
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             12524
_reflns_number_gt                9949
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.925
_reflns_Friedel_fraction_max     0.879
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_cell_refinement       
'CrysalisPRO 171.38.43 (Rigaku Oxford Diffraction 2015)'
_computing_data_reduction        
'CrysalisPRO 171.38.43 (Rigaku Oxford Diffraction 2015)'
_computing_structure_solution    
'SHELXT (G. M. Sheldrick Acta Cryst. (2015). A71, 3-8)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.9418 1 0 0 0 1 0 0 0 1
2 0.0582 0 0 1 0 -1 0 1 0 0

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3746 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration syn
_refine_ls_number_reflns         12524
_refine_ls_number_parameters     542
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1263
_refine_ls_R_factor_gt           0.1049
_refine_ls_wR_factor_ref         0.3114
_refine_ls_wR_factor_gt          0.2918
_refine_ls_goodness_of_fit_ref   1.255
_refine_ls_restrained_S_all      1.255
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.8373(5) 0.31655(15) 0.1613(5) 0.0333(9) Uani 1 1 d . . . . .
O4 O 1.1511(5) 0.55837(15) 0.5493(4) 0.0347(9) Uani 1 1 d . . . . .
O3 O 0.8597(5) 0.67740(15) 0.1563(5) 0.0354(10) Uani 1 1 d . . . . .
O1 O 0.4439(5) 0.43569(15) -0.1476(5) 0.0340(9) Uani 1 1 d . . . . .
N5 N 0.4559(5) 0.29865(16) -0.0829(5) 0.0260(9) Uani 1 1 d . . . . .
N9 N 0.9939(5) 0.52125(17) 0.3314(5) 0.0272(9) Uani 1 1 d . . . . .
N4 N 0.6642(6) 0.37635(16) 0.0126(5) 0.0263(9) Uani 1 1 d . . . . .
H4 H 0.5785 0.3775 -0.0602 0.032 Uiso 1 1 calc R U . . .
N2 N 0.6657(6) 0.47265(16) 0.0113(5) 0.0271(9) Uani 1 1 d . . . . .
N7 N 1.0061(5) 0.61736(16) 0.3274(5) 0.0266(9) Uani 1 1 d . . . . .
H7 H 1.0837 0.6160 0.4086 0.032 Uiso 1 1 calc R U . . .
N8 N 0.8489(6) 0.56872(18) 0.1308(5) 0.0334(11) Uani 1 1 d . . . . .
H8C H 0.8106 0.5383 0.0886 0.040 Uiso 1 1 calc R U . . .
H8D H 0.8199 0.5994 0.0852 0.040 Uiso 1 1 calc R U . . .
N10 N 1.0117(5) 0.42531(17) 0.4893(5) 0.0262(9) Uani 1 1 d . . . . .
N3 N 0.8687(6) 0.42525(18) 0.1614(5) 0.0302(10) Uani 1 1 d . . . . .
H3A H 0.9141 0.4558 0.1945 0.036 Uiso 1 1 calc R U . . .
H3B H 0.9131 0.3945 0.1944 0.036 Uiso 1 1 calc R U . . .
N1 N 0.5068(5) 0.57150(16) -0.0204(5) 0.0266(9) Uani 1 1 d . . . . .
C35 C 0.9498(6) 0.56848(19) 0.2621(6) 0.0260(10) Uani 1 1 d . . . . .
N6 N 1.0945(6) 0.69451(17) 0.5327(5) 0.0271(9) Uani 1 1 d . . . . .
C19 C 0.2156(7) 0.3186(2) -0.0789(7) 0.0320(12) Uani 1 1 d . . . . .
H19A H 0.2256 0.3571 -0.0970 0.038 Uiso 1 1 calc R U . . .
H19B H 0.1673 0.3004 -0.1720 0.038 Uiso 1 1 calc R U . . .
C36 C 1.0919(6) 0.51948(19) 0.4695(6) 0.0269(11) Uani 1 1 d . . . . .
C12 C 0.7337(6) 0.42552(19) 0.0619(5) 0.0243(10) Uani 1 1 d . . . . .
C11 C 0.5251(6) 0.4747(2) -0.0872(6) 0.0261(10) Uani 1 1 d . . . . .
C31 C 1.2798(8) 0.7344(2) 0.4805(7) 0.0369(13) Uani 1 1 d . . . . .
H31A H 1.3306 0.7017 0.4700 0.044 Uiso 1 1 calc R U . . .
H31B H 1.3458 0.7657 0.4981 0.044 Uiso 1 1 calc R U . . .
C13 C 0.7163(7) 0.32609(19) 0.0666(6) 0.0269(11) Uani 1 1 d . . . . .
C20 C 0.1199(8) 0.3131(3) 0.0024(7) 0.0391(13) Uani 1 1 d . . . . .
H20A H 0.0971 0.2747 0.0075 0.047 Uiso 1 1 calc R U . . .
H20B H 0.0267 0.3323 -0.0499 0.047 Uiso 1 1 calc R U . . .
C18 C 0.3690(7) 0.2942(2) 0.0020(6) 0.0288(11) Uani 1 1 d . . . . .
H18 H 0.3566 0.2551 0.0167 0.035 Uiso 1 1 calc R U . . .
C16 C 0.5187(8) 0.2658(3) -0.2651(8) 0.0408(15) Uani 1 1 d . . . . .
H16A H 0.5284 0.3001 -0.3088 0.049 Uiso 1 1 calc R U . . .
H16B H 0.5043 0.2362 -0.3338 0.049 Uiso 1 1 calc R U . . .
C30 C 1.2275(7) 0.7279(2) 0.5978(6) 0.0308(12) Uani 1 1 d . . . . .
H30A H 1.3022 0.7097 0.6814 0.037 Uiso 1 1 calc R U . . .
H30B H 1.2046 0.7633 0.6278 0.037 Uiso 1 1 calc R U . . .
C34 C 0.9511(7) 0.66821(19) 0.2764(6) 0.0274(11) Uani 1 1 d . . . . .
C9 C 0.5196(7) 0.5547(2) -0.2407(6) 0.0315(11) Uani 1 1 d . . . . .
H9A H 0.6266 0.5506 -0.2065 0.038 Uiso 1 1 calc R U . . .
H9B H 0.4707 0.5377 -0.3353 0.038 Uiso 1 1 calc R U . . .
C40 C 1.0734(7) 0.3701(2) 0.5134(6) 0.0289(11) Uani 1 1 d . . . . .
H40A H 1.0184 0.3466 0.4312 0.035 Uiso 1 1 calc R U . . .
H40B H 1.0701 0.3542 0.5999 0.035 Uiso 1 1 calc R U . . .
C17 C 0.3940(7) 0.2681(2) -0.2179(6) 0.0319(12) Uani 1 1 d . . . . .
H17A H 0.3084 0.2869 -0.2894 0.038 Uiso 1 1 calc R U . . .
H17B H 0.3644 0.2315 -0.2026 0.038 Uiso 1 1 calc R U . . .
C28 C 1.0923(7) 0.6735(2) 0.7659(6) 0.0317(12) Uani 1 1 d . . . . .
H28A H 1.1255 0.6364 0.7608 0.038 Uiso 1 1 calc R U . . .
H28B H 1.1800 0.6962 0.8135 0.038 Uiso 1 1 calc R U . . .
C39 C 1.2352(7) 0.3771(2) 0.5318(7) 0.0324(12) Uani 1 1 d . . . . .
H39A H 1.3043 0.3724 0.6325 0.039 Uiso 1 1 calc R U . . .
H39B H 1.2594 0.3508 0.4727 0.039 Uiso 1 1 calc R U . . .
C27 C 1.0021(8) 0.6736(3) 0.8543(7) 0.0425(15) Uani 1 1 d . . . . .
H27A H 0.9739 0.7109 0.8649 0.051 Uiso 1 1 calc R U . . .
H27B H 1.0619 0.6593 0.9504 0.051 Uiso 1 1 calc R U . . .
C37 C 1.1351(7) 0.46288(18) 0.5329(6) 0.0268(11) Uani 1 1 d . . . . .
H37 H 1.1817 0.4654 0.6390 0.032 Uiso 1 1 calc R U . . .
C38 C 1.2397(7) 0.4349(2) 0.4813(6) 0.0296(11) Uani 1 1 d . . . . .
H38A H 1.3392 0.4503 0.5262 0.035 Uiso 1 1 calc R U . . .
H38B H 1.2043 0.4369 0.3766 0.035 Uiso 1 1 calc R U . . .
C7 C 0.5033(7) 0.6249(2) -0.0879(6) 0.0306(12) Uani 1 1 d . . . . .
H7A H 0.5974 0.6439 -0.0383 0.037 Uiso 1 1 calc R U . . .
H7B H 0.4243 0.6475 -0.0833 0.037 Uiso 1 1 calc R U . . .
C29 C 1.0047(7) 0.6947(2) 0.6140(6) 0.0301(11) Uani 1 1 d . . . . .
H29 H 0.9738 0.7325 0.6200 0.036 Uiso 1 1 calc R U . . .
C14 C 0.6099(6) 0.28043(19) -0.0080(6) 0.0283(11) Uani 1 1 d . . . . .
H14 H 0.6161 0.2522 0.0632 0.034 Uiso 1 1 calc R U . . .
C8 C 0.4756(7) 0.6138(2) -0.2439(7) 0.0321(12) Uani 1 1 d . . . . .
H8A H 0.3716 0.6193 -0.3081 0.038 Uiso 1 1 calc R U . . .
H8B H 0.5367 0.6373 -0.2748 0.038 Uiso 1 1 calc R U . . .
C46 C 0.7648(8) 0.4014(3) 0.4712(8) 0.0407(15) Uani 1 1 d . . . . .
H46A H 0.7930 0.3633 0.4941 0.049 Uiso 1 1 calc R U . . .
H46B H 0.7271 0.4058 0.3668 0.049 Uiso 1 1 calc R U . . .
C33 C 1.0183(7) 0.7133(2) 0.3841(6) 0.0302(11) Uani 1 1 d . . . . .
H33 H 0.9398 0.7392 0.3781 0.036 Uiso 1 1 calc R U . . .
C41 C 0.9005(7) 0.4373(2) 0.5434(7) 0.0329(12) Uani 1 1 d . . . . .
H41 H 0.8679 0.4751 0.5145 0.040 Uiso 1 1 calc R U . . .
C45 C 0.6433(9) 0.4157(3) 0.5199(9) 0.0493(17) Uani 1 1 d . . . . .
H45A H 0.6071 0.4525 0.4871 0.059 Uiso 1 1 calc R U . . .
H45B H 0.5607 0.3905 0.4757 0.059 Uiso 1 1 calc R U . . .
C44 C 0.6977(9) 0.4130(3) 0.6810(9) 0.0492(18) Uani 1 1 d . . . . .
H44A H 0.6186 0.4241 0.7090 0.059 Uiso 1 1 calc R U . . .
H44B H 0.7255 0.3756 0.7135 0.059 Uiso 1 1 calc R U . . .
C21 C 0.1929(9) 0.3358(3) 0.1530(8) 0.0456(16) Uani 1 1 d . . . . .
H21A H 0.1325 0.3273 0.2057 0.055 Uiso 1 1 calc R U . . .
H21B H 0.2000 0.3754 0.1485 0.055 Uiso 1 1 calc R U . . .
C32 C 1.1348(8) 0.7435(2) 0.3485(7) 0.0375(14) Uani 1 1 d . . . . .
H32A H 1.1403 0.7283 0.2621 0.045 Uiso 1 1 calc R U . . .
H32B H 1.1117 0.7823 0.3332 0.045 Uiso 1 1 calc R U . . .
C23 C 0.4412(8) 0.3206(3) 0.1487(7) 0.0392(14) Uani 1 1 d . . . . .
H23A H 0.4531 0.3596 0.1376 0.047 Uiso 1 1 calc R U . . .
H23B H 0.5392 0.3048 0.2019 0.047 Uiso 1 1 calc R U . . .
C15 C 0.6524(8) 0.2553(3) -0.1249(8) 0.0419(15) Uani 1 1 d . . . . .
H15A H 0.7404 0.2730 -0.1255 0.050 Uiso 1 1 calc R U . . .
H15B H 0.6714 0.2163 -0.1088 0.050 Uiso 1 1 calc R U . . .
C22 C 0.3469(8) 0.3118(4) 0.2324(7) 0.0464(16) Uani 1 1 d . . . . .
H22A H 0.3948 0.3290 0.3270 0.056 Uiso 1 1 calc R U . . .
H22B H 0.3388 0.2728 0.2469 0.056 Uiso 1 1 calc R U . . .
C6 C 0.4221(8) 0.5713(2) 0.0670(7) 0.0354(13) Uani 1 1 d . . . . .
H6 H 0.3234 0.5865 0.0078 0.043 Uiso 1 1 calc R U . . .
C25 C 0.7727(10) 0.6580(5) 0.6292(9) 0.063(2) Uani 1 1 d . . . . .
H25A H 0.6885 0.6336 0.5826 0.075 Uiso 1 1 calc R U . . .
H25B H 0.7342 0.6945 0.6315 0.075 Uiso 1 1 calc R U . . .
C26 C 0.8628(10) 0.6387(4) 0.7826(9) 0.058(2) Uani 1 1 d . . . . .
H26A H 0.8908 0.6006 0.7814 0.069 Uiso 1 1 calc R U . . .
H26B H 0.8027 0.6412 0.8380 0.069 Uiso 1 1 calc R U . . .
C10 C 0.4634(7) 0.53143(19) -0.1327(6) 0.0268(10) Uani 1 1 d . . . . .
H10 H 0.3543 0.5294 -0.1791 0.032 Uiso 1 1 calc R U . . .
C24 C 0.8653(8) 0.6593(3) 0.5423(7) 0.0419(15) Uani 1 1 d . . . . .
H24A H 0.8055 0.6736 0.4462 0.050 Uiso 1 1 calc R U . . .
H24B H 0.8948 0.6222 0.5314 0.050 Uiso 1 1 calc R U . . .
C1 C 0.4955(8) 0.6084(2) 0.1959(7) 0.0385(14) Uani 1 1 d . . . . .
H1A H 0.5940 0.5944 0.2559 0.046 Uiso 1 1 calc R U . . .
H1B H 0.5068 0.6447 0.1627 0.046 Uiso 1 1 calc R U . . .
C2 C 0.4061(9) 0.6122(3) 0.2844(8) 0.0428(15) Uani 1 1 d . . . . .
H2A H 0.3104 0.6289 0.2270 0.051 Uiso 1 1 calc R U . . .
H2B H 0.4578 0.6352 0.3684 0.051 Uiso 1 1 calc R U . . .
C42 C 0.9529(9) 0.4350(3) 0.7062(8) 0.0456(16) Uani 1 1 d . . . . .
H42A H 1.0354 0.4602 0.7512 0.055 Uiso 1 1 calc R U . . .
H42B H 0.9884 0.3983 0.7401 0.055 Uiso 1 1 calc R U . . .
C43 C 0.8286(10) 0.4498(4) 0.7510(9) 0.055(2) Uani 1 1 d . . . . .
H43A H 0.8647 0.4469 0.8557 0.066 Uiso 1 1 calc R U . . .
H43B H 0.7986 0.4875 0.7239 0.066 Uiso 1 1 calc R U . . .
C5 C 0.4004(11) 0.5160(2) 0.1157(9) 0.0492(19) Uani 1 1 d . . . . .
H5A H 0.4967 0.4998 0.1736 0.059 Uiso 1 1 calc R U . . .
H5B H 0.3501 0.4927 0.0317 0.059 Uiso 1 1 calc R U . . .
C3 C 0.3819(11) 0.5555(3) 0.3341(9) 0.0520(18) Uani 1 1 d . . . . .
H3C H 0.4769 0.5400 0.3987 0.062 Uiso 1 1 calc R U . . .
H3D H 0.3194 0.5584 0.3869 0.062 Uiso 1 1 calc R U . . .
C4 C 0.3088(13) 0.5187(3) 0.2047(11) 0.064(3) Uani 1 1 d . . . . .
H4A H 0.2100 0.5325 0.1449 0.077 Uiso 1 1 calc R U . . .
H4B H 0.2983 0.4822 0.2372 0.077 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C13 1.230(8) . ?
O4 C36 1.251(6) . ?
O3 C34 1.222(7) . ?
O1 C11 1.256(7) . ?
N5 C18 1.474(7) . ?
N5 C17 1.481(7) . ?
N5 C14 1.488(7) . ?
N9 C35 1.352(6) . ?
N9 C36 1.359(8) . ?
N4 C13 1.381(6) . ?
N4 C12 1.396(6) . ?
N4 H4 0.8800 . ?
N2 C12 1.349(6) . ?
N2 C11 1.360(8) . ?
N7 C35 1.392(6) . ?
N7 C34 1.394(6) . ?
N7 H7 0.8800 . ?
N8 C35 1.316(8) . ?
N8 H8C 0.8800 . ?
N8 H8D 0.8800 . ?
N10 C37 1.468(7) . ?
N10 C41 1.471(7) . ?
N10 C40 1.485(6) . ?
N3 C12 1.322(8) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N1 C10 1.453(7) . ?
N1 C6 1.473(8) . ?
N1 C7 1.494(7) . ?
N6 C29 1.463(8) . ?
N6 C33 1.479(8) . ?
N6 C30 1.480(8) . ?
C19 C20 1.521(9) . ?
C19 C18 1.544(8) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C36 C37 1.538(7) . ?
C11 C10 1.534(7) . ?
C31 C30 1.513(8) . ?
C31 C32 1.547(10) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C13 C14 1.532(7) . ?
C20 C21 1.527(10) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C18 C23 1.531(9) . ?
C18 H18 1.0000 . ?
C16 C17 1.520(9) . ?
C16 C15 1.538(11) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C34 C33 1.528(8) . ?
C9 C8 1.532(8) . ?
C9 C10 1.554(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C40 C39 1.567(9) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C28 C27 1.528(9) . ?
C28 C29 1.541(8) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C39 C38 1.537(7) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C27 C26 1.552(11) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C37 C38 1.528(8) . ?
C37 H37 1.0000 . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C7 C8 1.541(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C29 C24 1.560(9) . ?
C29 H29 1.0000 . ?
C14 C15 1.566(8) . ?
C14 H14 1.0000 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C46 C41 1.540(9) . ?
C46 C45 1.542(9) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C33 C32 1.556(9) . ?
C33 H33 1.0000 . ?
C41 C42 1.540(9) . ?
C41 H41 1.0000 . ?
C45 C44 1.523(12) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C44 C43 1.519(13) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C21 C22 1.542(11) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C23 C22 1.537(9) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C6 C5 1.511(8) . ?
C6 C1 1.535(9) . ?
C6 H6 1.0000 . ?
C25 C24 1.536(10) . ?
C25 C26 1.540(13) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C10 H10 1.0000 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C1 C2 1.525(9) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.552(11) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C42 C43 1.545(10) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C5 C4 1.547(10) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C3 C4 1.533(13) . ?
C3 H3C 0.9900 . ?
C3 H3D 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 N5 C17 113.5(4) . . ?
C18 N5 C14 114.3(4) . . ?
C17 N5 C14 106.1(4) . . ?
C35 N9 C36 121.4(4) . . ?
C13 N4 C12 126.6(5) . . ?
C13 N4 H4 116.7 . . ?
C12 N4 H4 116.7 . . ?
C12 N2 C11 121.8(5) . . ?
C35 N7 C34 126.2(5) . . ?
C35 N7 H7 116.9 . . ?
C34 N7 H7 116.9 . . ?
C35 N8 H8C 120.0 . . ?
C35 N8 H8D 120.0 . . ?
H8C N8 H8D 120.0 . . ?
C37 N10 C41 115.6(4) . . ?
C37 N10 C40 107.2(4) . . ?
C41 N10 C40 117.0(4) . . ?
C12 N3 H3A 120.0 . . ?
C12 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C10 N1 C6 115.2(4) . . ?
C10 N1 C7 107.3(4) . . ?
C6 N1 C7 112.3(4) . . ?
N8 C35 N9 119.6(5) . . ?
N8 C35 N7 118.8(5) . . ?
N9 C35 N7 121.6(5) . . ?
C29 N6 C33 114.5(4) . . ?
C29 N6 C30 113.1(4) . . ?
C33 N6 C30 106.1(4) . . ?
C20 C19 C18 112.7(5) . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
O4 C36 N9 127.5(5) . . ?
O4 C36 C37 117.0(5) . . ?
N9 C36 C37 115.6(4) . . ?
N3 C12 N2 120.0(5) . . ?
N3 C12 N4 118.5(4) . . ?
N2 C12 N4 121.5(5) . . ?
O1 C11 N2 127.1(5) . . ?
O1 C11 C10 117.4(5) . . ?
N2 C11 C10 115.4(5) . . ?
C30 C31 C32 102.0(5) . . ?
C30 C31 H31A 111.4 . . ?
C32 C31 H31A 111.4 . . ?
C30 C31 H31B 111.4 . . ?
C32 C31 H31B 111.4 . . ?
H31A C31 H31B 109.2 . . ?
O2 C13 N4 125.6(5) . . ?
O2 C13 C14 120.9(4) . . ?
N4 C13 C14 113.5(5) . . ?
C19 C20 C21 112.3(6) . . ?
C19 C20 H20A 109.1 . . ?
C21 C20 H20A 109.1 . . ?
C19 C20 H20B 109.1 . . ?
C21 C20 H20B 109.1 . . ?
H20A C20 H20B 107.9 . . ?
N5 C18 C23 113.6(5) . . ?
N5 C18 C19 110.7(4) . . ?
C23 C18 C19 109.1(5) . . ?
N5 C18 H18 107.8 . . ?
C23 C18 H18 107.8 . . ?
C19 C18 H18 107.8 . . ?
C17 C16 C15 102.8(5) . . ?
C17 C16 H16A 111.2 . . ?
C15 C16 H16A 111.2 . . ?
C17 C16 H16B 111.2 . . ?
C15 C16 H16B 111.2 . . ?
H16A C16 H16B 109.1 . . ?
N6 C30 C31 104.1(5) . . ?
N6 C30 H30A 110.9 . . ?
C31 C30 H30A 110.9 . . ?
N6 C30 H30B 110.9 . . ?
C31 C30 H30B 110.9 . . ?
H30A C30 H30B 109.0 . . ?
O3 C34 N7 124.6(5) . . ?
O3 C34 C33 121.5(5) . . ?
N7 C34 C33 113.8(5) . . ?
C8 C9 C10 100.7(4) . . ?
C8 C9 H9A 111.6 . . ?
C10 C9 H9A 111.6 . . ?
C8 C9 H9B 111.6 . . ?
C10 C9 H9B 111.6 . . ?
H9A C9 H9B 109.4 . . ?
N10 C40 C39 105.0(4) . . ?
N10 C40 H40A 110.7 . . ?
C39 C40 H40A 110.7 . . ?
N10 C40 H40B 110.7 . . ?
C39 C40 H40B 110.7 . . ?
H40A C40 H40B 108.8 . . ?
N5 C17 C16 103.8(5) . . ?
N5 C17 H17A 111.0 . . ?
C16 C17 H17A 111.0 . . ?
N5 C17 H17B 111.0 . . ?
C16 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
C27 C28 C29 112.1(5) . . ?
C27 C28 H28A 109.2 . . ?
C29 C28 H28A 109.2 . . ?
C27 C28 H28B 109.2 . . ?
C29 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
C38 C39 C40 103.7(5) . . ?
C38 C39 H39A 111.0 . . ?
C40 C39 H39A 111.0 . . ?
C38 C39 H39B 111.0 . . ?
C40 C39 H39B 111.0 . . ?
H39A C39 H39B 109.0 . . ?
C28 C27 C26 110.8(5) . . ?
C28 C27 H27A 109.5 . . ?
C26 C27 H27A 109.5 . . ?
C28 C27 H27B 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 108.1 . . ?
N10 C37 C38 102.7(4) . . ?
N10 C37 C36 113.4(5) . . ?
C38 C37 C36 112.5(4) . . ?
N10 C37 H37 109.3 . . ?
C38 C37 H37 109.3 . . ?
C36 C37 H37 109.3 . . ?
C37 C38 C39 100.8(4) . . ?
C37 C38 H38A 111.6 . . ?
C39 C38 H38A 111.6 . . ?
C37 C38 H38B 111.6 . . ?
C39 C38 H38B 111.6 . . ?
H38A C38 H38B 109.4 . . ?
N1 C7 C8 106.7(4) . . ?
N1 C7 H7A 110.4 . . ?
C8 C7 H7A 110.4 . . ?
N1 C7 H7B 110.4 . . ?
C8 C7 H7B 110.4 . . ?
H7A C7 H7B 108.6 . . ?
N6 C29 C28 110.7(5) . . ?
N6 C29 C24 111.8(5) . . ?
C28 C29 C24 108.3(5) . . ?
N6 C29 H29 108.7 . . ?
C28 C29 H29 108.7 . . ?
C24 C29 H29 108.7 . . ?
N5 C14 C13 113.4(4) . . ?
N5 C14 C15 106.0(5) . . ?
C13 C14 C15 109.1(5) . . ?
N5 C14 H14 109.4 . . ?
C13 C14 H14 109.4 . . ?
C15 C14 H14 109.4 . . ?
C9 C8 C7 102.9(4) . . ?
C9 C8 H8A 111.2 . . ?
C7 C8 H8A 111.2 . . ?
C9 C8 H8B 111.2 . . ?
C7 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
C41 C46 C45 111.8(5) . . ?
C41 C46 H46A 109.3 . . ?
C45 C46 H46A 109.3 . . ?
C41 C46 H46B 109.3 . . ?
C45 C46 H46B 109.3 . . ?
H46A C46 H46B 107.9 . . ?
N6 C33 C34 114.0(4) . . ?
N6 C33 C32 106.2(5) . . ?
C34 C33 C32 109.4(5) . . ?
N6 C33 H33 109.1 . . ?
C34 C33 H33 109.1 . . ?
C32 C33 H33 109.1 . . ?
N10 C41 C46 111.0(5) . . ?
N10 C41 C42 115.7(6) . . ?
C46 C41 C42 110.1(5) . . ?
N10 C41 H41 106.5 . . ?
C46 C41 H41 106.5 . . ?
C42 C41 H41 106.5 . . ?
C44 C45 C46 111.7(7) . . ?
C44 C45 H45A 109.3 . . ?
C46 C45 H45A 109.3 . . ?
C44 C45 H45B 109.3 . . ?
C46 C45 H45B 109.3 . . ?
H45A C45 H45B 107.9 . . ?
C43 C44 C45 110.1(6) . . ?
C43 C44 H44A 109.6 . . ?
C45 C44 H44A 109.6 . . ?
C43 C44 H44B 109.6 . . ?
C45 C44 H44B 109.6 . . ?
H44A C44 H44B 108.1 . . ?
C20 C21 C22 110.8(6) . . ?
C20 C21 H21A 109.5 . . ?
C22 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C31 C32 C33 104.4(5) . . ?
C31 C32 H32A 110.9 . . ?
C33 C32 H32A 110.9 . . ?
C31 C32 H32B 110.9 . . ?
C33 C32 H32B 110.9 . . ?
H32A C32 H32B 108.9 . . ?
C18 C23 C22 110.1(5) . . ?
C18 C23 H23A 109.6 . . ?
C22 C23 H23A 109.6 . . ?
C18 C23 H23B 109.6 . . ?
C22 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
C16 C15 C14 104.3(5) . . ?
C16 C15 H15A 110.9 . . ?
C14 C15 H15A 110.9 . . ?
C16 C15 H15B 110.9 . . ?
C14 C15 H15B 110.9 . . ?
H15A C15 H15B 108.9 . . ?
C23 C22 C21 111.3(6) . . ?
C23 C22 H22A 109.4 . . ?
C21 C22 H22A 109.4 . . ?
C23 C22 H22B 109.4 . . ?
C21 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
N1 C6 C5 114.0(5) . . ?
N1 C6 C1 109.7(5) . . ?
C5 C6 C1 110.0(6) . . ?
N1 C6 H6 107.7 . . ?
C5 C6 H6 107.7 . . ?
C1 C6 H6 107.7 . . ?
C24 C25 C26 111.4(7) . . ?
C24 C25 H25A 109.3 . . ?
C26 C25 H25A 109.3 . . ?
C24 C25 H25B 109.3 . . ?
C26 C25 H25B 109.3 . . ?
H25A C25 H25B 108.0 . . ?
C25 C26 C27 110.4(7) . . ?
C25 C26 H26A 109.6 . . ?
C27 C26 H26A 109.6 . . ?
C25 C26 H26B 109.6 . . ?
C27 C26 H26B 109.6 . . ?
H26A C26 H26B 108.1 . . ?
N1 C10 C11 115.8(5) . . ?
N1 C10 C9 103.7(4) . . ?
C11 C10 C9 110.0(4) . . ?
N1 C10 H10 109.0 . . ?
C11 C10 H10 109.0 . . ?
C9 C10 H10 109.0 . . ?
C25 C24 C29 112.1(6) . . ?
C25 C24 H24A 109.2 . . ?
C29 C24 H24A 109.2 . . ?
C25 C24 H24B 109.2 . . ?
C29 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
C2 C1 C6 111.4(6) . . ?
C2 C1 H1A 109.3 . . ?
C6 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
C6 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
C1 C2 C3 110.6(5) . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C41 C42 C43 111.2(6) . . ?
C41 C42 H42A 109.4 . . ?
C43 C42 H42A 109.4 . . ?
C41 C42 H42B 109.4 . . ?
C43 C42 H42B 109.4 . . ?
H42A C42 H42B 108.0 . . ?
C44 C43 C42 111.2(6) . . ?
C44 C43 H43A 109.4 . . ?
C42 C43 H43A 109.4 . . ?
C44 C43 H43B 109.4 . . ?
C42 C43 H43B 109.4 . . ?
H43A C43 H43B 108.0 . . ?
C6 C5 C4 111.2(6) . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C4 C3 C2 109.8(6) . . ?
C4 C3 H3C 109.7 . . ?
C2 C3 H3C 109.7 . . ?
C4 C3 H3D 109.7 . . ?
C2 C3 H3D 109.7 . . ?
H3C C3 H3D 108.2 . . ?
C3 C4 C5 110.7(7) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?

_refine_diff_density_max         1.015
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.113

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

data_shelx_CCDC8
_database_code_depnum_ccdc_archive 'CCDC 1952644'
loop_
_audit_author_name
_audit_author_address
'Jeppe Christensen '
;national crystallography service (southampton) and diamond light source (didcot)
United Kingdom
;
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H17 N3 O'
_chemical_formula_sum            'C12 H17 N3 O'
_chemical_formula_weight         219.28

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'I 2'
_space_group_name_Hall           'I 2y'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   12.7286(3)
_cell_length_b                   13.6712(3)
_cell_length_c                   15.1669(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.349(3)
_cell_angle_gamma                90
_cell_volume                     2423.14(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    37817
_cell_measurement_theta_min      3.7770
_cell_measurement_theta_max      70.1520

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.632
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.31920
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.40a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC11 quarter χ goniometer'
_diffrn_measurement_device_type  
;
Rigaku 007HF equipped with Varimax confocal mirrors and an AFC11 goniometer 
and HyPix 6000 detector
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_radiation_collimation    'Varimax focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'Rotating anode'
_diffrn_source_type              'Rigaku 007 HF'
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_source_current           30.0
_diffrn_source_target            Cu
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0929603000
_diffrn_orient_matrix_UB_12      -0.0629896000
_diffrn_orient_matrix_UB_13      0.0130011000
_diffrn_orient_matrix_UB_21      -0.0925102000
_diffrn_orient_matrix_UB_22      0.0722044000
_diffrn_orient_matrix_UB_23      -0.0623187000
_diffrn_orient_matrix_UB_31      -0.0135512000
_diffrn_orient_matrix_UB_32      -0.0593382000
_diffrn_orient_matrix_UB_33      -0.0904559000

_diffrn_measurement_details      
;Data collection strategy using shutter-less operation of detector. 

List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00  94.00   0.50    1.50    --    5.00  59.00-180.00  356
  2  ω   -142.00  37.00   0.50    1.50    --  -52.30  59.00 -60.00  358
  3  ω   -142.00  37.00   0.50    1.50    --  -52.30  59.00-150.00  358
  4  ω   -142.00  37.00   0.50    1.50    --  -52.30  59.00   0.00  358
  5  ω   -142.00  37.00   0.50    1.50    --  -52.30  59.00 120.00  358
  6  ω   -142.00  37.00   0.50    1.50    --  -52.30  59.00 150.00  358
  7  ω   -142.00  37.00   0.50    1.50    --  -52.30  49.00-120.00  358
  8  ω   -142.00  37.00   0.50    1.50    --  -52.30  59.00  60.00  358
  9  ω   -142.00  37.00   0.50    1.50    --  -52.30  59.00 120.00  358
 10  ω   -179.00  -1.00   0.50    6.00    --  -90.00  59.00-122.89  356
 11  ω   -179.00  -1.00   0.50    6.00    --  -90.00  59.00 177.12  356
 12  ω   -179.00  -1.00   0.50    6.00    --  -90.00  57.00  43.05  356
 13  ω   -179.00  -1.00   0.50    6.00    --  -90.00  55.00-136.20  356
 14  ω   -179.00  -1.00   0.50    6.00    --  -90.00  57.00 -67.92  356
 15  ω   -179.00  -1.00   0.50    6.00    --  -90.00  55.00  28.08  356
 16  ω   -179.00  -1.00   0.50    6.00    --  -90.00  59.00 156.54  356
 17  ω   -179.00  -1.00   0.50    6.00    --  -90.00  59.00  55.84  356
 18  ω   -179.00  -1.00   0.50    6.00    --  -90.00  58.00  16.74  356
 19  ω   -179.00  -1.00   0.50    6.00    --  -90.00  58.00 -34.69  356
 20  ω   -179.00  -1.00   0.50    6.00    --  -90.00  57.00  43.05  356
 21  ω   -179.00  -1.00   0.50    6.00    --  -90.00  57.00 -48.00  356
 22  ω   -179.00  -1.00   0.50    6.00    --  -90.00  58.00 -15.88  356
 23  ω   -179.00  -1.00   0.50    6.00    --  -90.00  59.00  -1.21  356
 24  ω   -179.00  -1.00   0.50    6.00    --  -90.00  59.00-102.68  356
 25  ω   -179.00  -1.00   0.50    6.00    --  -90.00  59.00-102.68  356
 26  ω   -179.00  -1.00   0.50    6.00    --  -90.00  53.00 131.70  356
 27  ω   -166.00  -1.00   0.50    6.00    --  -90.00  58.00 122.37  330
 28  ω   -137.00  -1.00   0.50    6.00    --  -90.00  57.00-150.86  272
 29  ω   -165.00  -1.00   0.50    6.00    --  -90.00  59.00  88.14  328
 30  ω   -161.00  -1.00   0.50    6.00    --  -90.00  59.00 -88.24  320
;
_diffrn_reflns_number            53582
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.856
_diffrn_reflns_theta_max         70.563
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4618
_reflns_number_gt                4424
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.904
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.40a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.40a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.40a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0622P)²+0.4671P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1977 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(14)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4618
_refine_ls_number_parameters     324
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0980
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O -0.08626(12) -0.38715(12) -0.64501(11) 0.0378(4) Uani 1 1 d . . . . .
O1 O -0.42024(12) -0.59261(12) -0.36207(11) 0.0376(4) Uani 1 1 d . . . . .
N2 N -0.29730(15) -0.52984(13) -0.42211(12) 0.0320(4) Uani 1 1 d . . . . .
N1 N -0.33555(15) -0.58835(13) -0.50530(13) 0.0312(4) Uani 1 1 d . . . . .
N4 N -0.15457(15) -0.40221(13) -0.49228(13) 0.0315(4) Uani 1 1 d . . . . .
N5 N -0.18943(15) -0.46357(13) -0.57305(13) 0.0337(4) Uani 1 1 d . . . . .
N3 N -0.18756(15) -0.41884(14) -0.26920(14) 0.0375(4) Uani 1 1 d . . . . .
N6A N -0.24857(17) -0.60881(15) -0.70238(15) 0.0338(5) Uani 0.878 1 d D . P A 1
C18 C -0.15644(17) -0.44923(16) -0.64574(15) 0.0320(4) Uani 1 1 d . . . . .
C6 C -0.34314(16) -0.53562(15) -0.35634(14) 0.0310(4) Uani 1 1 d . . . . .
C17 C -0.20967(17) -0.31052(16) -0.50454(16) 0.0331(5) Uani 1 1 d . . . . .
C00C C -0.28640(18) -0.68268(15) -0.49344(15) 0.0323(4) Uani 1 1 d . . . . .
C16 C -0.32366(19) -0.29871(19) -0.56638(19) 0.0430(5) Uani 1 1 d . . . . .
H16 H -0.3632 -0.3504 -0.6053 0.052 Uiso 1 1 calc R U . . .
C19 C -0.2157(2) -0.51642(17) -0.73068(16) 0.0380(5) Uani 1 1 d D . . . .
H19A H -0.1671 -0.5274 -0.7662 0.046 Uiso 0.878(3) 1 calc R U P A 1
H19B H -0.2271 -0.4840 -0.7914 0.046 Uiso 0.122(3) 1 calc R U P A 2
C5 C -0.3526(2) -0.76018(17) -0.54680(17) 0.0410(5) Uani 1 1 d . . . . .
H5A H -0.4294 -0.7506 -0.5858 0.049 Uiso 1 1 calc R U . . .
C1 C -0.17156(19) -0.69795(17) -0.43587(17) 0.0362(5) Uani 1 1 d . . . . .
H1A H -0.1268 -0.6464 -0.4007 0.043 Uiso 1 1 calc R U . . .
C7 C -0.29634(18) -0.46064(18) -0.27648(17) 0.0366(5) Uani 1 1 d . . . . .
H7 H -0.2874 -0.4903 -0.2151 0.044 Uiso 1 1 calc R U . . .
C12 C -0.1513(2) -0.23237(17) -0.44759(18) 0.0407(5) Uani 1 1 d . . . . .
H12 H -0.0747 -0.2389 -0.4064 0.049 Uiso 1 1 calc R U . . .
C2 C -0.1233(2) -0.79029(19) -0.43083(19) 0.0449(6) Uani 1 1 d . . . . .
H2A H -0.0465 -0.8002 -0.3921 0.054 Uiso 1 1 calc R U . . .
C15 C -0.3784(2) -0.2106(2) -0.5703(2) 0.0506(6) Uani 1 1 d . . . . .
H15 H -0.4547 -0.2036 -0.6118 0.061 Uiso 1 1 calc R U . . .
C3 C -0.1888(2) -0.8669(2) -0.4828(2) 0.0510(6) Uani 1 1 d . . . . .
H3 H -0.1568 -0.9287 -0.4789 0.061 Uiso 1 1 calc R U . . .
C11 C -0.0882(2) -0.4777(2) -0.2141(2) 0.0474(6) Uani 1 1 d . . . . .
H11A H -0.0804 -0.4814 -0.1486 0.071 Uiso 1 1 calc R U . . .
H11B H -0.0209 -0.4483 -0.2165 0.071 Uiso 1 1 calc R U . . .
H11C H -0.0976 -0.5424 -0.2409 0.071 Uiso 1 1 calc R U . . .
C10 C -0.1825(2) -0.32005(17) -0.23063(18) 0.0431(5) Uani 1 1 d . . . . .
H10A H -0.1263 -0.2803 -0.2425 0.052 Uiso 1 1 calc R U . . .
H10B H -0.1643 -0.3215 -0.1622 0.052 Uiso 1 1 calc R U . . .
C13 C -0.2081(2) -0.14456(19) -0.4526(2) 0.0528(7) Uani 1 1 d . . . . .
H13 H -0.1690 -0.0925 -0.4141 0.063 Uiso 1 1 calc R U . . .
C8 C -0.3784(2) -0.3717(2) -0.2982(2) 0.0540(7) Uani 1 1 d . . . . .
H8A H -0.4364 -0.3754 -0.3631 0.065 Uiso 1 1 calc R U . . .
H8B H -0.4159 -0.3695 -0.2537 0.065 Uiso 1 1 calc R U . . .
C9 C -0.3032(2) -0.2822(2) -0.2864(2) 0.0504(6) Uani 1 1 d . . . . .
H9A H -0.3225 -0.2313 -0.2508 0.061 Uiso 1 1 calc R U . . .
H9B H -0.3113 -0.2565 -0.3483 0.061 Uiso 1 1 calc R U . . .
C22A C -0.3458(4) -0.6429(3) -0.7864(3) 0.0491(10) Uani 0.878(3) 1 d D . P A 1
H22A H -0.3870 -0.6943 -0.7696 0.059 Uiso 0.878(3) 1 calc R U P A 1
H22B H -0.3216 -0.6668 -0.8356 0.059 Uiso 0.878(3) 1 calc R U P A 1
C4 C -0.3033(2) -0.8511(2) -0.5413(2) 0.0515(6) Uani 1 1 d . . . . .
H4A H -0.3473 -0.9026 -0.5773 0.062 Uiso 1 1 calc R U . . .
C14 C -0.3214(2) -0.1329(2) -0.5136(2) 0.0553(7) Uani 1 1 d . . . . .
H14 H -0.3587 -0.0738 -0.5163 0.066 Uiso 1 1 calc R U . . .
C21A C -0.4179(2) -0.5520(3) -0.8192(2) 0.0542(8) Uani 0.878(3) 1 d D . P A 1
H21A H -0.4656 -0.5553 -0.8873 0.065 Uiso 0.878(3) 1 calc R U P A 1
H21B H -0.4666 -0.5436 -0.7841 0.065 Uiso 0.878(3) 1 calc R U P A 1
C23A C -0.1541(3) -0.6777(2) -0.6670(2) 0.0506(7) Uani 0.878(3) 1 d D . P A 1
H23A H -0.1254 -0.6892 -0.7159 0.076 Uiso 0.878(3) 1 calc R U P A 1
H23B H -0.1802 -0.7383 -0.6509 0.076 Uiso 0.878(3) 1 calc R U P A 1
H23C H -0.0941 -0.6513 -0.6110 0.076 Uiso 0.878(3) 1 calc R U P A 1
C20A C -0.3331(3) -0.4697(2) -0.7981(2) 0.0543(8) Uani 0.878(3) 1 d D . P A 1
H20A H -0.3538 -0.4163 -0.7659 0.065 Uiso 0.878(3) 1 calc R U P A 1
H20B H -0.3293 -0.4452 -0.8567 0.065 Uiso 0.878(3) 1 calc R U P A 1
C23B C -0.4160(19) -0.4982(18) -0.7842(17) 0.0506(7) Uani 0.122(3) 1 d D . P A
2
H23D H -0.4280 -0.4941 -0.8507 0.076 Uiso 0.122(3) 1 calc R U P A 2
H23E H -0.3990 -0.4344 -0.7557 0.076 Uiso 0.122(3) 1 calc R U P A 2
H23F H -0.4839 -0.5229 -0.7789 0.076 Uiso 0.122(3) 1 calc R U P A 2
N6B N -0.3218(12) -0.5630(11) -0.7350(11) 0.0338(5) Uani 0.122(3) 1 d D . P A 2
C20B C -0.132(2) -0.6122(16) -0.7125(17) 0.0543(8) Uani 0.122(3) 1 d D . P A 2
H20C H -0.1000 -0.6160 -0.7609 0.065 Uiso 0.122(3) 1 calc R U P A 2
H20D H -0.0695 -0.6091 -0.6496 0.065 Uiso 0.122(3) 1 calc R U P A 2
C21B C -0.2105(18) -0.7018(17) -0.720(2) 0.0542(8) Uani 0.122(3) 1 d D . P A 2
H21C H -0.1962 -0.7537 -0.7569 0.065 Uiso 0.122(3) 1 calc R U P A 2
H21D H -0.1968 -0.7268 -0.6561 0.065 Uiso 0.122(3) 1 calc R U P A 2
C22B C -0.335(3) -0.6638(19) -0.770(3) 0.0491(10) Uani 0.122(3) 1 d D . P A 2
H22C H -0.3621 -0.6665 -0.8391 0.059 Uiso 0.122(3) 1 calc R U P A 2
H22D H -0.3876 -0.7002 -0.7497 0.059 Uiso 0.122(3) 1 calc R U P A 2
H4 H -0.080(2) -0.396(2) -0.4642(19) 0.037(6) Uiso 1 1 d . . . . .
H1 H -0.411(3) -0.588(2) -0.535(2) 0.050(8) Uiso 1 1 d . . . . .
H2 H -0.252(2) -0.485(2) -0.4198(19) 0.040(7) Uiso 1 1 d . . . . .
H5 H -0.242(3) -0.511(2) -0.577(2) 0.054(8) 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 C18 1.229(3) . ?
O1 C6 1.229(3) . ?
N2 C6 1.343(3) . ?
N2 N1 1.408(2) . ?
N2 H2 0.83(3) . ?
N1 C00C 1.413(3) . ?
N1 H1 0.89(3) . ?
N4 N5 1.404(2) . ?
N4 C17 1.412(3) . ?
N4 H4 0.87(3) . ?
N5 C18 1.341(3) . ?
N5 H5 0.92(3) . ?
N3 C11 1.452(3) . ?
N3 C7 1.461(3) . ?
N3 C10 1.463(3) . ?
N6A C19 1.448(3) . ?
N6A C23A 1.453(3) . ?
N6A C22A 1.457(4) . ?
C18 C19 1.517(3) . ?
C6 C7 1.517(3) . ?
C17 C16 1.390(3) . ?
C17 C12 1.390(3) . ?
C00C C1 1.390(3) . ?
C00C C5 1.395(3) . ?
C16 C15 1.381(4) . ?
C16 H16 0.9300 . ?
C19 N6B 1.471(14) . ?
C19 C20A 1.573(4) . ?
C19 C20B 1.64(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C5 C4 1.380(4) . ?
C5 H5A 0.9300 . ?
C1 C2 1.393(3) . ?
C1 H1A 0.9300 . ?
C7 C8 1.551(4) . ?
C7 H7 0.9800 . ?
C12 C13 1.388(4) . ?
C12 H12 0.9300 . ?
C2 C3 1.376(4) . ?
C2 H2A 0.9300 . ?
C15 C14 1.378(4) . ?
C15 H15 0.9300 . ?
C3 C4 1.390(4) . ?
C3 H3 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C10 C9 1.521(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C13 C14 1.380(4) . ?
C13 H13 0.9300 . ?
C8 C9 1.519(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C22A C21A 1.507(5) . ?
C22A H22A 0.9700 . ?
C22A H22B 0.9700 . ?
C4 H4A 0.9300 . ?
C14 H14 0.9300 . ?
C21A C20A 1.503(5) . ?
C21A H21A 0.9700 . ?
C21A H21B 0.9700 . ?
C23A H23A 0.9600 . ?
C23A H23B 0.9600 . ?
C23A H23C 0.9600 . ?
C20A H20A 0.9700 . ?
C20A H20B 0.9700 . ?
C23B N6B 1.44(2) . ?
C23B H23D 0.9600 . ?
C23B H23E 0.9600 . ?
C23B H23F 0.9600 . ?
N6B C22B 1.46(2) . ?
C20B C21B 1.56(2) . ?
C20B H20C 0.9700 . ?
C20B H20D 0.9700 . ?
C21B C22B 1.56(2) . ?
C21B H21C 0.9700 . ?
C21B H21D 0.9700 . ?
C22B H22C 0.9700 . ?
C22B H22D 0.9700 . ?

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 N1 122.31(17) . . ?
C6 N2 H2 120.4(19) . . ?
N1 N2 H2 116.5(19) . . ?
N2 N1 C00C 115.21(16) . . ?
N2 N1 H1 112(2) . . ?
C00C N1 H1 114(2) . . ?
N5 N4 C17 116.53(17) . . ?
N5 N4 H4 113.0(18) . . ?
C17 N4 H4 111.3(19) . . ?
C18 N5 N4 122.46(17) . . ?
C18 N5 H5 120.1(19) . . ?
N4 N5 H5 117.1(19) . . ?
C11 N3 C7 114.2(2) . . ?
C11 N3 C10 113.05(19) . . ?
C7 N3 C10 106.35(19) . . ?
C19 N6A C23A 112.4(2) . . ?
C19 N6A C22A 105.3(2) . . ?
C23A N6A C22A 114.0(3) . . ?
O2 C18 N5 123.85(19) . . ?
O2 C18 C19 122.74(19) . . ?
N5 C18 C19 113.40(18) . . ?
O1 C6 N2 123.7(2) . . ?
O1 C6 C7 122.34(19) . . ?
N2 C6 C7 113.87(18) . . ?
C16 C17 C12 119.2(2) . . ?
C16 C17 N4 121.5(2) . . ?
C12 C17 N4 119.02(18) . . ?
C1 C00C C5 119.6(2) . . ?
C1 C00C N1 121.29(19) . . ?
C5 C00C N1 118.95(19) . . ?
C15 C16 C17 120.3(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
N6A C19 C18 112.42(19) . . ?
N6B C19 C18 116.0(6) . . ?
N6A C19 C20A 103.61(19) . . ?
C18 C19 C20A 109.3(2) . . ?
N6B C19 C20B 100.7(9) . . ?
C18 C19 C20B 105.6(8) . . ?
N6A C19 H19A 110.4 . . ?
C18 C19 H19A 110.4 . . ?
C20A C19 H19A 110.4 . . ?
N6B C19 H19B 111.3 . . ?
C18 C19 H19B 111.3 . . ?
C20B C19 H19B 111.3 . . ?
C4 C5 C00C 119.6(2) . . ?
C4 C5 H5A 120.2 . . ?
C00C C5 H5A 120.2 . . ?
C00C C1 C2 120.1(2) . . ?
C00C C1 H1A 119.9 . . ?
C2 C1 H1A 119.9 . . ?
N3 C7 C6 112.66(18) . . ?
N3 C7 C8 104.3(2) . . ?
C6 C7 C8 109.99(18) . . ?
N3 C7 H7 109.9 . . ?
C6 C7 H7 109.9 . . ?
C8 C7 H7 109.9 . . ?
C13 C12 C17 119.5(2) . . ?
C13 C12 H12 120.3 . . ?
C17 C12 H12 120.3 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C14 C15 C16 120.9(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C10 C9 102.54(19) . . ?
N3 C10 H10A 111.3 . . ?
C9 C10 H10A 111.3 . . ?
N3 C10 H10B 111.3 . . ?
C9 C10 H10B 111.3 . . ?
H10A C10 H10B 109.2 . . ?
C14 C13 C12 121.4(3) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C9 C8 C7 105.47(18) . . ?
C9 C8 H8A 110.6 . . ?
C7 C8 H8A 110.6 . . ?
C9 C8 H8B 110.6 . . ?
C7 C8 H8B 110.6 . . ?
H8A C8 H8B 108.8 . . ?
C8 C9 C10 104.0(2) . . ?
C8 C9 H9A 111.0 . . ?
C10 C9 H9A 111.0 . . ?
C8 C9 H9B 111.0 . . ?
C10 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
N6A C22A C21A 102.7(3) . . ?
N6A C22A H22A 111.2 . . ?
C21A C22A H22A 111.2 . . ?
N6A C22A H22B 111.2 . . ?
C21A C22A H22B 111.2 . . ?
H22A C22A H22B 109.1 . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4A 119.5 . . ?
C3 C4 H4A 119.5 . . ?
C15 C14 C13 118.7(2) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C20A C21A C22A 104.8(3) . . ?
C20A C21A H21A 110.8 . . ?
C22A C21A H21A 110.8 . . ?
C20A C21A H21B 110.8 . . ?
C22A C21A H21B 110.8 . . ?
H21A C21A H21B 108.9 . . ?
N6A C23A H23A 109.5 . . ?
N6A C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
N6A C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
C21A C20A C19 104.5(2) . . ?
C21A C20A H20A 110.8 . . ?
C19 C20A H20A 110.8 . . ?
C21A C20A H20B 110.8 . . ?
C19 C20A H20B 110.8 . . ?
H20A C20A H20B 108.9 . . ?
N6B C23B H23D 109.5 . . ?
N6B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
N6B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
C23B N6B C22B 116.0(19) . . ?
C23B N6B C19 108.5(14) . . ?
C22B N6B C19 114(2) . . ?
C21B C20B C19 104.9(16) . . ?
C21B C20B H20C 110.8 . . ?
C19 C20B H20C 110.8 . . ?
C21B C20B H20D 110.8 . . ?
C19 C20B H20D 110.8 . . ?
H20C C20B H20D 108.8 . . ?
C22B C21B C20B 106(2) . . ?
C22B C21B H21C 110.5 . . ?
C20B C21B H21C 110.5 . . ?
C22B C21B H21D 110.5 . . ?
C20B C21B H21D 110.5 . . ?
H21C C21B H21D 108.7 . . ?
N6B C22B C21B 101(2) . . ?
N6B C22B H22C 111.6 . . ?
C21B C22B H22C 111.6 . . ?
N6B C22B H22D 111.6 . . ?
C21B C22B H22D 111.6 . . ?
H22C C22B H22D 109.4 . . ?

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_2017NCS0682
_database_code_depnum_ccdc_archive 'CCDC 1952649'
loop_
_audit_author_name
_audit_author_address
'Jeppe Christensen '
;national crystallography service (southampton) and diamond light source (didcot)
United Kingdom
;
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H24 N4 O3'
_chemical_formula_sum            'C20 H24 N4 O3'
_chemical_formula_weight         368.43

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.41730(10)
_cell_length_b                   13.9827(2)
_cell_length_c                   12.3897(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.2540(10)
_cell_angle_gamma                90
_cell_volume                     938.28(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6512
_cell_measurement_theta_min      4.7270
_cell_measurement_theta_max      70.1040

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    0.729
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_T_min  0.70980
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measurement_details      
;Data collection strategy using shutter-less operation of detector. 
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC11 quarter χ goniometer'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_radiation_collimation    'Varimax focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'Rotating anode'
_diffrn_source_type              'Rigaku 007 HF'
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_source_current           30.0
_diffrn_source_target            Cu
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_reflns_number            12000
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.568
_diffrn_reflns_theta_max         70.436
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3534
_reflns_number_gt                3409
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_max     0.970
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0335P)²+0.1281P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1532 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(9)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3534
_refine_ls_number_parameters     256
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0682
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2551(2) 0.47820(10) 0.83359(11) 0.0190(3) Uani 1 1 d . . . . .
O2 O 0.6669(2) 0.49860(10) 0.84413(11) 0.0204(3) Uani 1 1 d . . . . .
O3 O 1.0333(2) 0.41223(11) 0.46273(12) 0.0242(3) Uani 1 1 d . . . . .
N1 N 0.4633(3) 0.44957(12) 0.68427(13) 0.0178(3) Uani 1 1 d . . . . .
N3 N 0.6367(3) 0.40939(12) 0.52477(13) 0.0195(4) Uani 1 1 d . . . . .
N4 N 0.5751(3) 0.26275(13) 0.37298(14) 0.0223(4) Uani 1 1 d . . . . .
N2 N 0.8970(3) 0.46426(13) 0.66230(15) 0.0220(4) Uani 1 1 d . . . . .
C8 C 0.4836(3) 0.47701(13) 0.78970(15) 0.0167(4) Uani 1 1 d . . . . .
C9 C 0.6708(3) 0.44289(14) 0.62920(16) 0.0177(4) Uani 1 1 d . . . . .
C6 C 0.2527(3) 0.61381(14) 0.96080(16) 0.0184(4) Uani 1 1 d . . . . .
C10 C 0.8139(3) 0.39317(14) 0.44866(16) 0.0196(4) Uani 1 1 d . . . . .
C11 C 0.7111(4) 0.34979(15) 0.34448(17) 0.0207(4) Uani 1 1 d . . . . .
H11 H 0.8517 0.3318 0.2976 0.025 Uiso 1 1 calc R U . . .
C1 C 0.0580(4) 0.67000(15) 0.92147(18) 0.0211(4) Uani 1 1 d . . . . .
H1 H -0.0758 0.6413 0.8827 0.025 Uiso 1 1 calc R U . . .
C5 C 0.4476(3) 0.65668(15) 1.01725(17) 0.0211(4) Uani 1 1 d . . . . .
H5 H 0.5815 0.6187 1.0434 0.025 Uiso 1 1 calc R U . . .
C4 C 0.4480(4) 0.75459(16) 1.03576(17) 0.0240(4) Uani 1 1 d . . . . .
H4 H 0.5807 0.7833 1.0753 0.029 Uiso 1 1 calc R U . . .
C13 C 0.6574(4) 0.52228(15) 0.28237(17) 0.0229(4) Uani 1 1 d . . . . .
C2 C 0.0602(4) 0.76821(16) 0.93914(17) 0.0237(4) Uani 1 1 d . . . . .
H2 H -0.0718 0.8065 0.9119 0.028 Uiso 1 1 calc R U . . .
C7 C 0.2439(3) 0.50710(14) 0.94575(16) 0.0194(4) Uani 1 1 d . . . . .
H7A H 0.3840 0.4779 0.9864 0.023 Uiso 1 1 calc R U . . .
H7B H 0.0894 0.4823 0.9765 0.023 Uiso 1 1 calc R U . . .
C3 C 0.2543(4) 0.81052(16) 0.99642(18) 0.0249(5) Uani 1 1 d . . . . .
H3 H 0.2546 0.8776 1.0087 0.030 Uiso 1 1 calc R U . . .
C12 C 0.5469(4) 0.42299(15) 0.28388(17) 0.0229(4) Uani 1 1 d . . . . .
H12A H 0.5197 0.4010 0.2086 0.028 Uiso 1 1 calc R U . . .
H12B H 0.3842 0.4258 0.3186 0.028 Uiso 1 1 calc R U . . .
C19 C 0.7479(4) 0.18953(16) 0.4117(2) 0.0297(5) Uani 1 1 d . . . . .
H19A H 0.8496 0.2155 0.4712 0.045 Uiso 1 1 calc R U . . .
H19B H 0.6555 0.1340 0.4372 0.045 Uiso 1 1 calc R U . . .
H19C H 0.8544 0.1700 0.3527 0.045 Uiso 1 1 calc R U . . .
C20 C 0.4231(4) 0.22416(17) 0.28426(18) 0.0277(5) Uani 1 1 d . . . . .
H20A H 0.3073 0.2733 0.2583 0.042 Uiso 1 1 calc R U . . .
H20B H 0.5295 0.2047 0.2252 0.042 Uiso 1 1 calc R U . . .
H20C H 0.3307 0.1686 0.3098 0.042 Uiso 1 1 calc R U . . .
C14 C 0.8680(4) 0.54299(17) 0.22348(18) 0.0270(5) Uani 1 1 d . . . . .
H14 H 0.9445 0.4940 0.1829 0.032 Uiso 1 1 calc R U . . .
C15 C 0.9662(4) 0.63481(18) 0.22392(19) 0.0320(5) Uani 1 1 d . . . . .
H15 H 1.1093 0.6482 0.1836 0.038 Uiso 1 1 calc R U . . .
C18 C 0.5510(4) 0.59549(17) 0.3410(2) 0.0317(5) Uani 1 1 d . . . . .
H18 H 0.4081 0.5826 0.3817 0.038 Uiso 1 1 calc R U . . .
C16 C 0.8574(5) 0.70671(18) 0.2826(2) 0.0370(6) Uani 1 1 d . . . . .
H16 H 0.9251 0.7694 0.2827 0.044 Uiso 1 1 calc R U . . .
C17 C 0.6490(5) 0.68683(19) 0.3413(2) 0.0411(6) Uani 1 1 d . . . . .
H17 H 0.5732 0.7360 0.3818 0.049 Uiso 1 1 calc R U . . .
HN2A H 0.915(5) 0.482(2) 0.731(2) 0.035(7) Uiso 1 1 d . . . . .
HN2B H 1.024(5) 0.4526(19) 0.620(2) 0.031(7) Uiso 1 1 d . . . . .
HN3 H 0.491(6) 0.391(2) 0.506(2) 0.037(7) 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
O1 C8 1.363(2) . ?
O1 C7 1.450(2) . ?
O2 C8 1.226(2) . ?
O3 C10 1.226(2) . ?
N1 C9 1.331(2) . ?
N1 C8 1.364(2) . ?
N3 C10 1.379(3) . ?
N3 C9 1.385(3) . ?
N3 HN3 0.86(3) . ?
N4 C19 1.461(3) . ?
N4 C20 1.462(3) . ?
N4 C11 1.470(3) . ?
N2 C9 1.318(2) . ?
N2 HN2A 0.89(3) . ?
N2 HN2B 0.89(3) . ?
C6 C5 1.389(3) . ?
C6 C1 1.394(3) . ?
C6 C7 1.504(3) . ?
C10 C11 1.521(3) . ?
C11 C12 1.540(3) . ?
C11 H11 1.0000 . ?
C1 C2 1.391(3) . ?
C1 H1 0.9500 . ?
C5 C4 1.388(3) . ?
C5 H5 0.9500 . ?
C4 C3 1.389(3) . ?
C4 H4 0.9500 . ?
C13 C18 1.388(3) . ?
C13 C14 1.398(3) . ?
C13 C12 1.512(3) . ?
C2 C3 1.388(3) . ?
C2 H2 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C3 H3 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C14 C15 1.390(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(4) . ?
C15 H15 0.9500 . ?
C18 C17 1.383(4) . ?
C18 H18 0.9500 . ?
C16 C17 1.385(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

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
C8 O1 C7 116.33(14) . . ?
C9 N1 C8 117.34(16) . . ?
C10 N3 C9 127.86(16) . . ?
C10 N3 HN3 114.7(19) . . ?
C9 N3 HN3 117.1(19) . . ?
C19 N4 C20 109.53(17) . . ?
C19 N4 C11 109.78(16) . . ?
C20 N4 C11 113.70(17) . . ?
C9 N2 HN2A 116.4(17) . . ?
C9 N2 HN2B 119.9(16) . . ?
HN2A N2 HN2B 123(2) . . ?
O2 C8 O1 120.61(17) . . ?
O2 C8 N1 130.08(17) . . ?
O1 C8 N1 109.31(15) . . ?
N2 C9 N1 127.92(18) . . ?
N2 C9 N3 118.16(17) . . ?
N1 C9 N3 113.92(16) . . ?
C5 C6 C1 119.56(18) . . ?
C5 C6 C7 120.79(17) . . ?
C1 C6 C7 119.60(17) . . ?
O3 C10 N3 123.63(18) . . ?
O3 C10 C11 122.90(18) . . ?
N3 C10 C11 113.46(16) . . ?
N4 C11 C10 107.61(17) . . ?
N4 C11 C12 112.36(16) . . ?
C10 C11 C12 110.22(17) . . ?
N4 C11 H11 108.9 . . ?
C10 C11 H11 108.9 . . ?
C12 C11 H11 108.9 . . ?
C2 C1 C6 119.84(19) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C4 C5 C6 120.47(19) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C18 C13 C14 118.3(2) . . ?
C18 C13 C12 120.1(2) . . ?
C14 C13 C12 121.62(19) . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
O1 C7 C6 113.16(16) . . ?
O1 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
O1 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.8 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C13 C12 C11 113.06(16) . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
N4 C19 H19A 109.5 . . ?
N4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N4 C20 H20A 109.5 . . ?
N4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C18 C13 121.3(2) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
C15 C16 C17 119.5(2) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?

_refine_diff_density_max         0.135
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.029

####################################################################### 
# 
# 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_2017NCS0860
_database_code_depnum_ccdc_archive 'CCDC 1952646'
loop_
_audit_author_name
_audit_author_address
'Jeppe Christensen '
;national crystallography service (southampton) and diamond light source (didcot)
United Kingdom
;
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H84 N12 O12'
_chemical_formula_weight         973.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0010 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.7687(5)
_cell_length_b                   21.9014(12)
_cell_length_c                   13.1820(7)
_cell_angle_alpha                90
_cell_angle_beta                 89.865(5)
_cell_angle_gamma                90
_cell_volume                     2820.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2224
_cell_measurement_theta_max      26.064800318
_cell_measurement_theta_min      1.49751498504

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.022
_exptl_crystal_size_min          0.012
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_T_min  0.995673179095
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CCP4 7.0.048: AIMLESS, version 0.5.32 : 29/03/17
Scaling & analysis of unmerged intensities, 
absorption correction using spherical harmonics
;

_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_dtime           0.004
_diffrn_detector_type            'Dectris, PILATUS 2M'
_diffrn_measurement_details      
;Data collection strategy using shutter-less operation of detector. 
Three omega scans -170 to 25 with phi 0, 120 and 240 respectively.
0.1 degree images with 0.5 sec exposure
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_details 'custom build fixed Chi diffractometer'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_radiation_collimation    'focusing mirrors and 0.100 mm pinhole'
_diffrn_radiation_monochromator  'Si 111, double crystal monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_source_type              'DLS beamline I19, undulator'
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_wavelength_determination estimated

_diffrn_radiation_wavelength_details 'Zr absorption edge'
_diffrn_reflns_number            17512
_diffrn_reflns_av_unetI/netI     0.2730
_diffrn_reflns_av_R_equivalents  0.1767
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.748
_diffrn_reflns_theta_max         25.503
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.824
_diffrn_reflns_point_group_measured_fraction_full 0.826
_reflns_number_total             9516
_reflns_number_gt                2724
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.612
_reflns_Friedel_fraction_max     0.643
_reflns_Friedel_fraction_full    0.647

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'GDA 8.44; generic data acquisition software'
_computing_cell_refinement       
'XIA2 0.4.0.438-g4431aaa, Winter, G. (2010) J. Appl. Cryst. 43'
_computing_data_reduction        
'XIA2 0.4.0.438-g4431aaa, Winter, G. (2010) J. Appl. Cryst. 43'
_computing_structure_solution    'SHELXT Acta Cryst. (2015). A71, 3-8'

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 580 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.8(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         9516
_refine_ls_number_parameters     629
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2136
_refine_ls_R_factor_gt           0.0743
_refine_ls_wR_factor_ref         0.1955
_refine_ls_wR_factor_gt          0.1561
_refine_ls_goodness_of_fit_ref   0.676
_refine_ls_restrained_S_all      0.676
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 2.0160(5) 1.4197(2) 1.7907(4) 0.0495(15) Uani 1 1 d . . . . .
O1 O 1.5180(6) 1.4155(3) 1.6926(4) 0.0534(15) Uani 1 1 d . . . . .
O6 O 1.7744(6) 1.4453(3) 2.0305(4) 0.0620(17) Uani 1 1 d . . . . .
O11 O 2.0897(6) 1.5268(3) 2.0526(5) 0.0620(17) Uani 1 1 d . . . . .
N2 N 1.2928(7) 1.4260(3) 1.7225(5) 0.0434(17) Uani 1 1 d . . . . .
H2 H 1.2238 1.4216 1.7650 0.052 Uiso 1 1 calc R U . . .
N5 N 1.7853(7) 1.4192(3) 1.7726(5) 0.0453(17) Uani 1 1 d . . . . .
O5 O 1.7772(7) 1.3559(3) 1.9456(4) 0.0666(18) Uani 1 1 d . . . . .
O3 O 1.2764(7) 1.4496(3) 1.4628(5) 0.0717(19) Uani 1 1 d . . . . .
O12 O 2.0985(6) 1.6187(3) 1.9717(5) 0.0640(17) Uani 1 1 d . . . . .
O7 O 1.3565(6) 1.5713(3) 1.6888(5) 0.0612(16) Uani 1 1 d . . . . .
O8 O 1.6033(7) 1.5272(3) 1.4465(5) 0.0709(19) Uani 1 1 d . . . . .
O10 O 1.8583(6) 1.5646(3) 1.7995(5) 0.0618(16) Uani 1 1 d . . . . .
O9 O 1.6104(6) 1.6181(3) 1.5325(4) 0.0655(18) Uani 1 1 d . . . . .
O2 O 1.2780(7) 1.3597(3) 1.5504(5) 0.075(2) Uani 1 1 d . . . . .
N6 N 1.7664(7) 1.4471(3) 1.8645(5) 0.0490(18) Uani 1 1 d . . . . .
H6 H 1.7495 1.4865 1.8692 0.059 Uiso 1 1 calc R U . . .
N3 N 1.2719(6) 1.4529(3) 1.6285(5) 0.0488(18) Uani 1 1 d . . . . .
H3 H 1.2582 1.4925 1.6225 0.059 Uiso 1 1 calc R U . . .
N1 N 1.3043(7) 1.3779(3) 1.9054(5) 0.0552(18) Uani 1 1 d . . . . .
C6 C 1.4164(9) 1.4069(3) 1.7482(6) 0.043(2) Uani 1 1 d . . . . .
N9 N 1.6053(7) 1.5310(3) 1.6196(5) 0.0542(19) Uani 1 1 d . . . . .
H9 H 1.6193 1.4915 1.6250 0.065 Uiso 1 1 calc R U . . .
N11 N 2.0883(7) 1.5673(3) 1.7973(5) 0.0504(18) Uani 1 1 d . . . . .
H11 H 2.1614 1.5815 1.7659 0.060 Uiso 1 1 calc R U . . .
N7 N 1.5838(7) 1.6205(4) 1.8859(6) 0.068(2) Uani 1 1 d . . . . .
N8 N 1.5854(7) 1.5646(3) 1.7058(5) 0.0475(18) Uani 1 1 d . . . . .
H8 H 1.6558 1.5745 1.7439 0.057 Uiso 1 1 calc R U . . .
N12 N 2.1047(7) 1.5318(3) 1.8817(5) 0.0491(17) Uani 1 1 d . . . . .
H12 H 2.1215 1.4925 1.8751 0.059 Uiso 1 1 calc R U . . .
C17 C 1.9113(9) 1.4059(4) 1.7412(7) 0.048(2) Uani 1 1 d . . . . .
C18 C 1.7751(7) 1.4110(5) 1.9485(7) 0.049(2) Uani 1 1 d . . . . .
C7 C 1.2736(8) 1.4149(5) 1.5448(7) 0.055(2) Uani 1 1 d . . . . .
C39 C 2.0950(9) 1.5567(4) 1.9756(8) 0.056(2) Uani 1 1 d . . . . .
N10 N 2.0789(8) 1.6593(5) 1.6554(8) 0.088(3) Uani 1 1 d . . . . .
C5 C 1.4243(8) 1.3707(4) 1.8424(7) 0.054(2) Uani 1 1 d . . . . .
H5 H 1.5068 1.3838 1.8816 0.065 Uiso 1 1 calc R U . . .
C00U C 1.4596(9) 1.5824(4) 1.7326(7) 0.052(2) Uani 1 1 d . . . . .
C28 C 1.6044(9) 1.5569(5) 1.5254(9) 0.062(3) Uani 1 1 d . . . . .
C27 C 1.4557(9) 1.6216(4) 1.8293(8) 0.066(3) Uani 1 1 d . . . . .
H27 H 1.3796 1.6072 1.8741 0.079 Uiso 1 1 calc R U . . .
C16 C 1.9201(9) 1.3736(4) 1.6409(6) 0.053(2) Uani 1 1 d . . . . .
H16 H 2.0078 1.3503 1.6349 0.064 Uiso 1 1 calc R U . . .
N4 N 1.8044(10) 1.3341(5) 1.6264(7) 0.092(3) Uani 1 1 d . . . . .
C37 C 1.9658(9) 1.6153(4) 1.6601(7) 0.058(2) Uani 1 1 d . . . . .
H37 H 1.8764 1.6365 1.6494 0.069 Uiso 1 1 calc R U . . .
C38 C 1.9643(9) 1.5812(4) 1.7610(8) 0.061(3) Uani 1 1 d . . . . .
C19 C 1.7932(10) 1.4177(5) 2.1316(7) 0.065(3) Uani 1 1 d . . . . .
C40 C 2.0982(11) 1.6555(5) 2.0651(8) 0.073(3) Uani 1 1 d . . . . .
C34 C 2.1068(12) 1.6721(6) 1.5537(10) 0.098(4) Uani 1 1 d . . . . .
H34 H 2.1227 1.7104 1.5219 0.118 Uiso 1 1 calc R U . . .
C24 C 1.6198(12) 1.6818(5) 1.9108(10) 0.098(4) Uani 1 1 d . . . . .
H24A H 1.7198 1.6858 1.9209 0.118 Uiso 1 1 calc R U . . .
H24B H 1.5721 1.6954 1.9733 0.118 Uiso 1 1 calc R U . . .
C8 C 1.2970(10) 1.4212(6) 1.3623(7) 0.076(3) Uani 1 1 d . . . . .
C25 C 1.5723(12) 1.7195(5) 1.8182(10) 0.098(4) Uani 1 1 d . . . . .
H25A H 1.5643 1.7635 1.8342 0.118 Uiso 1 1 calc R U . . .
H25B H 1.6337 1.7139 1.7590 0.118 Uiso 1 1 calc R U . . .
C33 C 2.0497(13) 1.7148(5) 1.7112(10) 0.107(4) Uani 1 1 d . . . . .
H33A H 2.0367 1.7050 1.7831 0.160 Uiso 1 1 calc R U . . .
H33B H 1.9662 1.7336 1.6845 0.160 Uiso 1 1 calc R U . . .
H33C H 2.1264 1.7433 1.7037 0.160 Uiso 1 1 calc R U . . .
C26 C 1.4314(11) 1.6896(5) 1.8014(10) 0.099(4) Uani 1 1 d . . . . .
H26A H 1.4020 1.6937 1.7300 0.119 Uiso 1 1 calc R U . . .
H26B H 1.3612 1.7081 1.8461 0.119 Uiso 1 1 calc R U . . .
C20 C 1.9299(9) 1.3869(5) 2.1371(7) 0.078(3) Uani 1 1 d . . . . .
H20A H 2.0024 1.4172 2.1262 0.117 Uiso 1 1 calc R U . . .
H20B H 1.9357 1.3554 2.0845 0.117 Uiso 1 1 calc R U . . .
H20C H 1.9411 1.3681 2.2040 0.117 Uiso 1 1 calc R U . . .
C30 C 1.7360(11) 1.6448(6) 1.3771(9) 0.105(4) Uani 1 1 d . . . . .
H30A H 1.7138 1.6164 1.3221 0.158 Uiso 1 1 calc R U . . .
H30B H 1.8074 1.6270 1.4200 0.158 Uiso 1 1 calc R U . . .
H30C H 1.7690 1.6833 1.3483 0.158 Uiso 1 1 calc R U . . .
C29 C 1.6091(11) 1.6566(5) 1.4404(9) 0.082(3) Uani 1 1 d . . . . .
C1 C 1.3186(11) 1.4184(5) 1.9899(8) 0.090(4) Uani 1 1 d . . . . .
H1A H 1.3532 1.4579 1.9661 0.136 Uiso 1 1 calc R U . . .
H1B H 1.3830 1.4010 2.0388 0.136 Uiso 1 1 calc R U . . .
H1C H 1.2293 1.4242 2.0226 0.136 Uiso 1 1 calc R U . . .
C3 C 1.2904(15) 1.2796(6) 1.8405(10) 0.110(5) Uani 1 1 d . . . . .
H3A H 1.2890 1.2354 1.8566 0.133 Uiso 1 1 calc R U . . .
H3B H 1.2302 1.2876 1.7817 0.133 Uiso 1 1 calc R U . . .
C11 C 1.4285(11) 1.3884(6) 1.3608(8) 0.103(4) Uani 1 1 d . . . . .
H11A H 1.4336 1.3611 1.4195 0.154 Uiso 1 1 calc R U . . .
H11B H 1.5039 1.4178 1.3635 0.154 Uiso 1 1 calc R U . . .
H11C H 1.4356 1.3643 1.2983 0.154 Uiso 1 1 calc R U . . .
C21 C 1.7890(13) 1.4721(5) 2.2013(7) 0.103(4) Uani 1 1 d . . . . .
H21A H 1.6961 1.4889 2.2026 0.155 Uiso 1 1 calc R U . . .
H21B H 1.8529 1.5033 2.1766 0.155 Uiso 1 1 calc R U . . .
H21C H 1.8153 1.4595 2.2699 0.155 Uiso 1 1 calc R U . . .
C15 C 1.9005(13) 1.4160(6) 1.5497(9) 0.110(4) Uani 1 1 d . . . . .
H15A H 1.8688 1.4566 1.5729 0.132 Uiso 1 1 calc R U . . .
H15B H 1.9886 1.4214 1.5135 0.132 Uiso 1 1 calc R U . . .
C36 C 1.9993(12) 1.5738(5) 1.5677(8) 0.091(4) Uani 1 1 d . . . . .
H36A H 2.0359 1.5340 1.5905 0.109 Uiso 1 1 calc R U . . .
H36B H 1.9163 1.5666 1.5265 0.109 Uiso 1 1 calc R U . . .
C4 C 1.4334(14) 1.3023(5) 1.8223(9) 0.095(4) Uani 1 1 d . . . . .
H4A H 1.4627 1.2942 1.7516 0.114 Uiso 1 1 calc R U . . .
H4B H 1.4989 1.2826 1.8693 0.114 Uiso 1 1 calc R U . . .
C42 C 2.2318(12) 1.6436(6) 2.1205(9) 0.106(4) Uani 1 1 d . . . . .
H42A H 2.3083 1.6597 2.0803 0.159 Uiso 1 1 calc R U . . .
H42B H 2.2437 1.5996 2.1303 0.159 Uiso 1 1 calc R U . . .
H42C H 2.2296 1.6640 2.1867 0.159 Uiso 1 1 calc R U . . .
C43 C 1.9734(12) 1.6431(5) 2.1294(9) 0.099(4) Uani 1 1 d . . . . .
H43A H 1.9849 1.6042 2.1652 0.148 Uiso 1 1 calc R U . . .
H43B H 1.8924 1.6409 2.0859 0.148 Uiso 1 1 calc R U . . .
H43C H 1.9619 1.6761 2.1789 0.148 Uiso 1 1 calc R U . . .
C32 C 1.4800(11) 1.6461(5) 1.3813(9) 0.096(4) Uani 1 1 d . . . . .
H32A H 1.4009 1.6498 1.4267 0.145 Uiso 1 1 calc R U . . .
H32B H 1.4819 1.6051 1.3517 0.145 Uiso 1 1 calc R U . . .
H32C H 1.4731 1.6766 1.3271 0.145 Uiso 1 1 calc R U . . .
C14 C 1.8012(13) 1.3897(7) 1.4828(9) 0.110(4) Uani 1 1 d . . . . .
H14A H 1.8329 1.3911 1.4115 0.132 Uiso 1 1 calc R U . . .
H14B H 1.7122 1.4111 1.4882 0.132 Uiso 1 1 calc R U . . .
C23 C 1.5879(11) 1.5780(5) 1.9701(8) 0.087(3) Uani 1 1 d . . . . .
H23A H 1.5768 1.5363 1.9447 0.131 Uiso 1 1 calc R U . . .
H23B H 1.5136 1.5874 2.0177 0.131 Uiso 1 1 calc R U . . .
H23C H 1.6761 1.5816 2.0049 0.131 Uiso 1 1 calc R U . . .
C2 C 1.2509(13) 1.3181(5) 1.9315(9) 0.096(4) Uani 1 1 d . . . . .
H2A H 1.1503 1.3193 1.9406 0.115 Uiso 1 1 calc R U . . .
H2B H 1.2935 1.3023 1.9943 0.115 Uiso 1 1 calc R U . . .
C12 C 1.8238(16) 1.2776(6) 1.6796(10) 0.130(6) Uani 1 1 d . . . . .
H12A H 1.7731 1.2787 1.7438 0.195 Uiso 1 1 calc R U . . .
H12B H 1.9215 1.2717 1.6934 0.195 Uiso 1 1 calc R U . . .
H12C H 1.7902 1.2438 1.6379 0.195 Uiso 1 1 calc R U . . .
C10 C 1.2955(15) 1.4741(7) 1.2932(8) 0.130(5) Uani 1 1 d . . . . .
H10A H 1.3602 1.5050 1.3175 0.195 Uiso 1 1 calc R U . . .
H10B H 1.2032 1.4916 1.2913 0.195 Uiso 1 1 calc R U . . .
H10C H 1.3220 1.4610 1.2249 0.195 Uiso 1 1 calc R U . . .
C35 C 2.1052(13) 1.6081(6) 1.5072(10) 0.114(5) Uani 1 1 d . . . . .
H35A H 2.0795 1.6098 1.4347 0.136 Uiso 1 1 calc R U . . .
H35B H 2.1961 1.5885 1.5133 0.136 Uiso 1 1 calc R U . . .
C22 C 1.6780(11) 1.3733(6) 2.1520(7) 0.094(4) Uani 1 1 d . . . . .
H22A H 1.6853 1.3387 2.1052 0.141 Uiso 1 1 calc R U . . .
H22B H 1.5900 1.3939 2.1420 0.141 Uiso 1 1 calc R U . . .
H22C H 1.6840 1.3586 2.2221 0.141 Uiso 1 1 calc R U . . .
C31 C 1.6121(13) 1.7205(5) 1.4849(9) 0.102(4) Uani 1 1 d . . . . .
H31A H 1.6913 1.7246 1.5300 0.154 Uiso 1 1 calc R U . . .
H31B H 1.5279 1.7278 1.5236 0.154 Uiso 1 1 calc R U . . .
H31C H 1.6192 1.7505 1.4300 0.154 Uiso 1 1 calc R U . . .
C41 C 2.0931(14) 1.7189(5) 2.0227(9) 0.109(4) Uani 1 1 d . . . . .
H41A H 2.0100 1.7237 1.9820 0.163 Uiso 1 1 calc R U . . .
H41B H 2.1737 1.7259 1.9799 0.163 Uiso 1 1 calc R U . . .
H41C H 2.0922 1.7485 2.0784 0.163 Uiso 1 1 calc R U . . .
C9 C 1.1798(11) 1.3764(7) 1.3409(8) 0.118(5) Uani 1 1 d . . . . .
H9A H 1.0925 1.3985 1.3412 0.177 Uiso 1 1 calc R U . . .
H9B H 1.1781 1.3448 1.3935 0.177 Uiso 1 1 calc R U . . .
H9C H 1.1938 1.3574 1.2745 0.177 Uiso 1 1 calc R U . . .
C13 C 1.7898(15) 1.3228(6) 1.5213(10) 0.121(5) Uani 1 1 d . . . . .
H13A H 1.7000 1.3044 1.5050 0.145 Uiso 1 1 calc R U . . .
H13B H 1.8642 1.2967 1.4944 0.145 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C17 1.252(10) . ?
O1 C6 1.247(9) . ?
O6 C18 1.316(10) . ?
O6 C19 1.475(10) . ?
O11 C39 1.209(10) . ?
N2 C6 1.323(10) . ?
N2 N3 1.388(8) . ?
N2 H2 0.8800 . ?
N5 C17 1.330(10) . ?
N5 N6 1.369(8) . ?
O5 C18 1.208(10) . ?
O3 C7 1.321(10) . ?
O3 C8 1.476(10) . ?
O12 C39 1.359(10) . ?
O12 C40 1.471(10) . ?
O7 C00U 1.188(10) . ?
O8 C28 1.227(11) . ?
O10 C38 1.208(10) . ?
O9 C28 1.346(10) . ?
O9 C29 1.479(11) . ?
O2 C7 1.214(11) . ?
N6 C18 1.364(10) . ?
N6 H6 0.8800 . ?
N3 C7 1.383(11) . ?
N3 H3 0.8800 . ?
N1 C1 1.432(11) . ?
N1 C5 1.443(10) . ?
N1 C2 1.451(12) . ?
C6 C5 1.474(11) . ?
N9 C28 1.364(12) . ?
N9 N8 1.368(8) . ?
N9 H9 0.8800 . ?
N11 C38 1.338(10) . ?
N11 N12 1.368(9) . ?
N11 H11 0.8800 . ?
N7 C24 1.427(12) . ?
N7 C23 1.449(11) . ?
N7 C27 1.459(11) . ?
N8 C00U 1.335(10) . ?
N8 H8 0.8800 . ?
N12 C39 1.356(11) . ?
N12 H12 0.8800 . ?
C17 C16 1.502(11) . ?
N10 C34 1.395(13) . ?
N10 C33 1.447(13) . ?
N10 C37 1.469(11) . ?
C5 C4 1.525(12) . ?
C5 H5 1.0000 . ?
C00U C27 1.537(13) . ?
C27 C26 1.551(13) . ?
C27 H27 1.0000 . ?
C16 N4 1.436(12) . ?
C16 C15 1.531(15) . ?
C16 H16 1.0000 . ?
N4 C13 1.415(13) . ?
N4 C12 1.436(14) . ?
C37 C38 1.526(12) . ?
C37 C36 1.553(12) . ?
C37 H37 1.0000 . ?
C19 C20 1.498(13) . ?
C19 C21 1.505(12) . ?
C19 C22 1.510(13) . ?
C40 C41 1.498(15) . ?
C40 C43 1.508(14) . ?
C40 C42 1.519(14) . ?
C34 C35 1.530(16) . ?
C34 H34 0.9500 . ?
C24 C25 1.545(15) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C8 C11 1.473(14) . ?
C8 C10 1.474(15) . ?
C8 C9 1.535(15) . ?
C25 C26 1.541(14) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C30 C29 1.515(14) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C29 C32 1.501(15) . ?
C29 C31 1.518(15) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C4 1.502(16) . ?
C3 C2 1.516(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C15 C14 1.433(15) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C36 C35 1.505(14) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C14 C13 1.554(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O6 C19 120.5(7) . . ?
C6 N2 N3 119.9(6) . . ?
C6 N2 H2 120.0 . . ?
N3 N2 H2 120.0 . . ?
C17 N5 N6 119.7(7) . . ?
C7 O3 C8 119.7(8) . . ?
C39 O12 C40 121.0(8) . . ?
C28 O9 C29 120.7(9) . . ?
C18 N6 N5 116.8(7) . . ?
C18 N6 H6 121.6 . . ?
N5 N6 H6 121.6 . . ?
C7 N3 N2 117.1(7) . . ?
C7 N3 H3 121.5 . . ?
N2 N3 H3 121.5 . . ?
C1 N1 C5 115.7(8) . . ?
C1 N1 C2 114.3(9) . . ?
C5 N1 C2 109.3(8) . . ?
O1 C6 N2 121.8(7) . . ?
O1 C6 C5 122.3(8) . . ?
N2 C6 C5 115.8(7) . . ?
C28 N9 N8 122.2(8) . . ?
C28 N9 H9 118.9 . . ?
N8 N9 H9 118.9 . . ?
C38 N11 N12 121.8(7) . . ?
C38 N11 H11 119.1 . . ?
N12 N11 H11 119.1 . . ?
C24 N7 C23 114.9(9) . . ?
C24 N7 C27 108.3(8) . . ?
C23 N7 C27 115.3(8) . . ?
C00U N8 N9 120.4(7) . . ?
C00U N8 H8 119.8 . . ?
N9 N8 H8 119.8 . . ?
C39 N12 N11 120.4(7) . . ?
C39 N12 H12 119.8 . . ?
N11 N12 H12 119.8 . . ?
O4 C17 N5 122.8(8) . . ?
O4 C17 C16 121.8(8) . . ?
N5 C17 C16 115.3(8) . . ?
O5 C18 O6 126.7(9) . . ?
O5 C18 N6 123.7(9) . . ?
O6 C18 N6 109.6(9) . . ?
O2 C7 O3 128.5(9) . . ?
O2 C7 N3 123.5(9) . . ?
O3 C7 N3 107.9(9) . . ?
O11 C39 N12 123.4(9) . . ?
O11 C39 O12 125.0(9) . . ?
N12 C39 O12 111.5(9) . . ?
C34 N10 C33 110.9(10) . . ?
C34 N10 C37 108.6(10) . . ?
C33 N10 C37 112.5(9) . . ?
N1 C5 C6 112.5(7) . . ?
N1 C5 C4 104.7(8) . . ?
C6 C5 C4 112.6(8) . . ?
N1 C5 H5 109.0 . . ?
C6 C5 H5 109.0 . . ?
C4 C5 H5 109.0 . . ?
O7 C00U N8 126.3(9) . . ?
O7 C00U C27 119.9(8) . . ?
N8 C00U C27 113.8(8) . . ?
O8 C28 O9 126.0(10) . . ?
O8 C28 N9 123.5(9) . . ?
O9 C28 N9 110.4(10) . . ?
N7 C27 C00U 113.3(7) . . ?
N7 C27 C26 105.6(8) . . ?
C00U C27 C26 110.1(8) . . ?
N7 C27 H27 109.3 . . ?
C00U C27 H27 109.3 . . ?
C26 C27 H27 109.3 . . ?
N4 C16 C17 110.9(7) . . ?
N4 C16 C15 99.3(9) . . ?
C17 C16 C15 113.6(8) . . ?
N4 C16 H16 110.9 . . ?
C17 C16 H16 110.9 . . ?
C15 C16 H16 110.9 . . ?
C13 N4 C16 108.5(9) . . ?
C13 N4 C12 109.9(10) . . ?
C16 N4 C12 110.5(10) . . ?
N10 C37 C38 111.4(8) . . ?
N10 C37 C36 101.1(8) . . ?
C38 C37 C36 113.6(8) . . ?
N10 C37 H37 110.2 . . ?
C38 C37 H37 110.2 . . ?
C36 C37 H37 110.2 . . ?
O10 C38 N11 123.9(9) . . ?
O10 C38 C37 121.3(8) . . ?
N11 C38 C37 114.5(8) . . ?
O6 C19 C20 109.9(7) . . ?
O6 C19 C21 102.9(8) . . ?
C20 C19 C21 110.5(9) . . ?
O6 C19 C22 109.3(8) . . ?
C20 C19 C22 111.5(9) . . ?
C21 C19 C22 112.5(9) . . ?
O12 C40 C41 101.2(8) . . ?
O12 C40 C43 111.8(8) . . ?
C41 C40 C43 110.4(9) . . ?
O12 C40 C42 108.0(8) . . ?
C41 C40 C42 111.5(10) . . ?
C43 C40 C42 113.2(10) . . ?
N10 C34 C35 101.5(10) . . ?
N10 C34 H34 129.3 . . ?
C35 C34 H34 129.3 . . ?
N7 C24 C25 104.2(9) . . ?
N7 C24 H24A 110.9 . . ?
C25 C24 H24A 110.9 . . ?
N7 C24 H24B 110.9 . . ?
C25 C24 H24B 110.9 . . ?
H24A C24 H24B 108.9 . . ?
C11 C8 C10 112.7(10) . . ?
C11 C8 O3 109.5(8) . . ?
C10 C8 O3 102.8(9) . . ?
C11 C8 C9 109.7(11) . . ?
C10 C8 C9 112.4(10) . . ?
O3 C8 C9 109.5(7) . . ?
C26 C25 C24 99.0(9) . . ?
C26 C25 H25A 112.0 . . ?
C24 C25 H25A 112.0 . . ?
C26 C25 H25B 112.0 . . ?
C24 C25 H25B 112.0 . . ?
H25A C25 H25B 109.7 . . ?
N10 C33 H33A 109.5 . . ?
N10 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
N10 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C25 C26 C27 103.7(8) . . ?
C25 C26 H26A 111.0 . . ?
C27 C26 H26A 111.0 . . ?
C25 C26 H26B 111.0 . . ?
C27 C26 H26B 111.0 . . ?
H26A C26 H26B 109.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O9 C29 C32 110.3(9) . . ?
O9 C29 C30 110.3(8) . . ?
C32 C29 C30 112.1(11) . . ?
O9 C29 C31 102.0(9) . . ?
C32 C29 C31 111.0(10) . . ?
C30 C29 C31 110.8(10) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C3 C2 100.2(9) . . ?
C4 C3 H3A 111.7 . . ?
C2 C3 H3A 111.7 . . ?
C4 C3 H3B 111.7 . . ?
C2 C3 H3B 111.7 . . ?
H3A C3 H3B 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C14 C15 C16 109.0(11) . . ?
C14 C15 H15A 109.9 . . ?
C16 C15 H15A 109.9 . . ?
C14 C15 H15B 109.9 . . ?
C16 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
C35 C36 C37 105.5(10) . . ?
C35 C36 H36A 110.6 . . ?
C37 C36 H36A 110.6 . . ?
C35 C36 H36B 110.6 . . ?
C37 C36 H36B 110.6 . . ?
H36A C36 H36B 108.8 . . ?
C3 C4 C5 104.1(9) . . ?
C3 C4 H4A 110.9 . . ?
C5 C4 H4A 110.9 . . ?
C3 C4 H4B 110.9 . . ?
C5 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
C40 C42 H42A 109.5 . . ?
C40 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C40 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C40 C43 H43A 109.5 . . ?
C40 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C40 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C15 C14 C13 103.1(11) . . ?
C15 C14 H14A 111.1 . . ?
C13 C14 H14A 111.1 . . ?
C15 C14 H14B 111.1 . . ?
C13 C14 H14B 111.1 . . ?
H14A C14 H14B 109.1 . . ?
N7 C23 H23A 109.5 . . ?
N7 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N7 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N1 C2 C3 102.9(8) . . ?
N1 C2 H2A 111.2 . . ?
C3 C2 H2A 111.2 . . ?
N1 C2 H2B 111.2 . . ?
C3 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
N4 C12 H12A 109.5 . . ?
N4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C36 C35 C34 104.6(10) . . ?
C36 C35 H35A 110.8 . . ?
C34 C35 H35A 110.8 . . ?
C36 C35 H35B 110.8 . . ?
C34 C35 H35B 110.8 . . ?
H35A C35 H35B 108.9 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C13 C14 98.4(10) . . ?
N4 C13 H13A 112.1 . . ?
C14 C13 H13A 112.1 . . ?
N4 C13 H13B 112.1 . . ?
C14 C13 H13B 112.1 . . ?
H13A C13 H13B 109.7 . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_2017NCS0681
_database_code_depnum_ccdc_archive 'CCDC 1952647'
loop_
_audit_author_name
_audit_author_address
'Jeppe Christensen '
;national crystallography service (southampton) and diamond light source (didcot)
United Kingdom
;
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 N4 O3'
_chemical_formula_sum            'C14 H20 N4 O3'
_chemical_formula_weight         292.34

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   12.4402(4)
_cell_length_b                   12.9330(4)
_cell_length_c                   19.1393(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.889(3)
_cell_angle_gamma                90
_cell_volume                     3033.55(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4151
_cell_measurement_theta_min      4.1110
_cell_measurement_theta_max      69.6780

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.758
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_T_min  0.41117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'

_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC11 quarter χ goniometer'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_radiation_collimation    'Varimax focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'Rotating anode'
_diffrn_source_type              'Rigaku 007 HF'
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_source_current           30.0
_diffrn_source_target            Cu
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_reflns_number            11819
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.145
_diffrn_reflns_theta_max         70.439
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2837
_reflns_number_gt                2357
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0279748000
_diffrn_orient_matrix_UB_12      0.0338948000
_diffrn_orient_matrix_UB_13      -0.0718829000
_diffrn_orient_matrix_UB_21      0.0807771000
_diffrn_orient_matrix_UB_22      0.0805644000
_diffrn_orient_matrix_UB_23      0.0379606000
_diffrn_orient_matrix_UB_31      0.0921807000
_diffrn_orient_matrix_UB_32      -0.0810287000
_diffrn_orient_matrix_UB_33      0.0076636000
_diffrn_measurement_details      
;
Data collection strategy using shutter-less operation of detector. 
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00   6.00   0.50   30.00    --    5.00  47.00 156.00   50
  2  ω    -39.00  -1.00   0.50   30.00    --  -90.00  47.00 156.00   76
  3  ω   -143.00 -47.00   0.50   30.00    --  -90.00  47.00 156.00  192
  4  ω    -88.00  72.00   0.50    5.00    --    0.00  47.00 156.00  320
  5  ω    -33.00   5.00   0.50    5.00    --    0.00  60.00-180.00   76
  6  ω   -178.00  -1.00   0.50   30.00    --  -90.00  29.00  30.00  354
  7  ω    -94.00  -5.00   0.50   30.00    --  -90.00  43.00-150.00  178
  8  ω   -167.00-141.00   0.50   30.00    --  -90.00  60.00  90.00   52
  9  ω   -137.00-110.00   0.50   30.00    --  -90.00  60.00  90.00   54
 10  ω   -136.00 -84.00   0.50   30.00    --  -90.00  29.00 -60.00  104
 11  ω    -82.00  -9.00   0.50   30.00    --  -90.00  60.00  90.00  146
 12  ω    -47.00 -20.00   0.50   30.00    --  -90.00  29.00 -60.00   54
 13  ω   -144.00-108.00   0.50   30.00    --  -90.00  43.00-150.00   72
 14  ω    -54.00 -28.00   0.50   30.00    --  -90.00   0.00-150.00   52
 15  ω   -178.00  -1.00   0.50   30.00    --  -90.00  60.00-120.00  354
;
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXTL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+54.1975P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2837
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1479
_refine_ls_R_factor_gt           0.1348
_refine_ls_wR_factor_ref         0.2952
_refine_ls_wR_factor_gt          0.2896
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5324(3) 0.2406(3) 0.4909(2) 0.0337(10) Uani 1 1 d . . . . .
O2 O 0.3690(4) 0.2249(3) 0.4191(3) 0.0435(12) Uani 1 1 d . . . . .
N1 N 0.4370(4) 0.3835(4) 0.4669(3) 0.0324(12) Uani 1 1 d . . . . .
N2 N 0.3596(5) 0.5422(5) 0.4498(4) 0.0411(14) Uani 1 1 d . . . . .
N4 N 0.1092(5) 0.2884(5) 0.3160(3) 0.0439(14) Uiso 1 1 d . . . . .
C6 C 0.6320(5) 0.1204(5) 0.4278(3) 0.0337(14) Uani 1 1 d . . . . .
C8 C 0.4367(5) 0.2798(5) 0.4546(3) 0.0342(14) Uani 1 1 d . . . . .
C9 C 0.3545(5) 0.4416(5) 0.4369(3) 0.0346(14) Uani 1 1 d . . . . .
C1 C 0.6656(5) 0.2030(5) 0.3904(3) 0.0339(14) Uani 1 1 d . . . . .
H1 H 0.6387 0.2705 0.3968 0.041 Uiso 1 1 calc R U . . .
C2 C 0.7378(6) 0.1878(5) 0.3439(3) 0.0386(15) Uani 1 1 d . . . . .
H2 H 0.7601 0.2454 0.3191 0.046 Uiso 1 1 calc R U . . .
C5 C 0.6735(5) 0.0211(5) 0.4173(3) 0.0374(15) Uani 1 1 d . . . . .
H5 H 0.6522 -0.0364 0.4426 0.045 Uiso 1 1 calc R U . . .
C4 C 0.7439(6) 0.0076(5) 0.3709(4) 0.0410(16) Uani 1 1 d . . . . .
H4 H 0.7707 -0.0598 0.3641 0.049 Uiso 1 1 calc R U . . .
C7 C 0.5550(5) 0.1334(5) 0.4804(4) 0.0375(15) Uani 1 1 d . . . . .
H7A H 0.4859 0.0966 0.4627 0.045 Uiso 1 1 calc R U . . .
H7B H 0.5879 0.1020 0.5263 0.045 Uiso 1 1 calc R U . . .
C3 C 0.7780(6) 0.0911(6) 0.3328(4) 0.0454(17) Uani 1 1 d . . . . .
H3 H 0.8271 0.0811 0.3005 0.054 Uiso 1 1 calc R U . . .
N3A N 0.2529(9) 0.4009(9) 0.4027(6) 0.0277(16) Uiso 0.507(6) 1 d . . P A 1
O3A O 0.1602(8) 0.5504(8) 0.3677(5) 0.0334(15) Uiso 0.507(6) 1 d . . P A 1
C10A C 0.1665(11) 0.4573(10) 0.3683(7) 0.032(2) Uiso 0.507(6) 1 d . . P A 1
C12A C -0.0189(12) 0.4479(13) 0.2913(8) 0.038(2) Uiso 0.507(6) 1 d . . P A 1
H12A H 0.0108 0.4617 0.2480 0.057 Uiso 0.507(6) 1 calc R U P A 1
H12B H -0.0371 0.5135 0.3121 0.057 Uiso 0.507(6) 1 calc R U P A 1
H12C H -0.0848 0.4055 0.2798 0.057 Uiso 0.507(6) 1 calc R U P A 1
C11A C 0.0637(10) 0.3918(10) 0.3430(7) 0.0350(19) Uani 0.507(6) 1 d . . P A 1
H11A H 0.0299 0.3750 0.3854 0.042 Uiso 0.507(6) 1 calc R U P A 1
C13A C 0.1324(12) 0.2901(12) 0.2525(7) 0.046(2) Uani 0.507(6) 1 d . . P A 1
H13A H 0.1597 0.2221 0.2412 0.068 Uiso 0.507(6) 1 calc R U P A 1
H13B H 0.1885 0.3425 0.2500 0.068 Uiso 0.507(6) 1 calc R U P A 1
H13C H 0.0667 0.3069 0.2183 0.068 Uiso 0.507(6) 1 calc R U P A 1
C14A C 0.0175(12) 0.2106(11) 0.3240(8) 0.047(2) Uani 0.507(6) 1 d . . P A 1
H14A H -0.0460 0.2235 0.2871 0.071 Uiso 0.507(6) 1 calc R U P A 1
H14B H -0.0033 0.2190 0.3708 0.071 Uiso 0.507(6) 1 calc R U P A 1
H14C H 0.0439 0.1399 0.3193 0.071 Uiso 0.507(6) 1 calc R U P A 1
O3B O 0.1811(8) 0.5544(8) 0.3488(5) 0.0334(15) Uiso 0.493(6) 1 d . . P A 2
C10B C 0.1905(11) 0.4625(10) 0.3443(7) 0.032(2) Uiso 0.493(6) 1 d . . P A 2
N3B N 0.2733(9) 0.4056(10) 0.3855(6) 0.0277(16) Uiso 0.493(6) 1 d . . P A 2
C11B C 0.1147(10) 0.3969(10) 0.2916(7) 0.0350(19) Uani 0.493(6) 1 d . . P A 2
H11B H 0.1471 0.3946 0.2473 0.042 Uiso 0.493(6) 1 calc R U P A 2
C13B C 0.0867(12) 0.2197(12) 0.2486(8) 0.046(2) Uani 0.493(6) 1 d . . P A 2
H13D H 0.1138 0.1496 0.2604 0.068 Uiso 0.493(6) 1 calc R U P A 2
H13E H 0.1242 0.2488 0.2120 0.068 Uiso 0.493(6) 1 calc R U P A 2
H13F H 0.0081 0.2173 0.2308 0.068 Uiso 0.493(6) 1 calc R U P A 2
C14B C 0.0619(12) 0.2633(12) 0.3669(8) 0.047(2) Uani 0.493(6) 1 d . . P A 2
H14D H 0.0790 0.3142 0.4051 0.071 Uiso 0.493(6) 1 calc R U P A 2
H14E H 0.0872 0.1949 0.3846 0.071 Uiso 0.493(6) 1 calc R U P A 2
H14F H -0.0172 0.2615 0.3505 0.071 Uiso 0.493(6) 1 calc R U P A 2
C12B C 0.0036(12) 0.4458(13) 0.2719(8) 0.038(2) Uiso 0.493(6) 1 d . . P A 2
H12D H -0.0427 0.4019 0.2373 0.057 Uiso 0.493(6) 1 calc R U P A 2
H12E H 0.0111 0.5141 0.2511 0.057 Uiso 0.493(6) 1 calc R U P A 2
H12F H -0.0298 0.4530 0.3144 0.057 Uiso 0.493(6) 1 calc R U P A 2
HN2A H 0.313(5) 0.573(5) 0.428(3) 0.025(18) Uiso 1 1 d . . . . .
HN2B H 0.412(7) 0.564(6) 0.478(4) 0.05(2) Uiso 1 1 d . . . . .
HN3 H 0.269(6) 0.339(6) 0.387(4) 0.05(2) 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
O1 C8 1.368(7) . ?
O1 C7 1.436(7) . ?
O2 C8 1.216(7) . ?
N1 C9 1.321(8) . ?
N1 C8 1.363(8) . ?
N2 C9 1.324(8) . ?
N2 HN2A 0.76(7) . ?
N2 HN2B 0.82(8) . ?
N4 C14B 1.264(16) . ?
N4 C13A 1.296(15) . ?
N4 C11B 1.484(14) . ?
N4 C14A 1.548(15) . ?
N4 C13B 1.551(14) . ?
N4 C11A 1.574(14) . ?
C6 C1 1.390(9) . ?
C6 C5 1.411(9) . ?
C6 C7 1.514(9) . ?
C9 N3B 1.365(13) . ?
C9 N3A 1.421(13) . ?
C1 C2 1.382(9) . ?
C1 H1 0.9500 . ?
C2 C3 1.377(9) . ?
C2 H2 0.9500 . ?
C5 C4 1.361(10) . ?
C5 H5 0.9500 . ?
C4 C3 1.409(10) . ?
C4 H4 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C3 H3 0.9500 . ?
N3A C10A 1.370(17) . ?
N3A HN3 0.89(8) . ?
O3A C10A 1.206(16) . ?
C10A C11A 1.540(17) . ?
C12A C11A 1.487(19) . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C11A H11A 1.0000 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
O3B C10B 1.198(16) . ?
C10B N3B 1.395(18) . ?
C10B C11B 1.516(17) . ?
N3B HN3 0.86(8) . ?
C11B C12B 1.508(19) . ?
C11B H11B 1.0000 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C7 117.4(5) . . ?
C9 N1 C8 120.4(5) . . ?
C9 N2 HN2A 114(5) . . ?
C9 N2 HN2B 118(6) . . ?
HN2A N2 HN2B 128(8) . . ?
C14B N4 C11B 122.5(10) . . ?
C13A N4 C14A 113.0(10) . . ?
C14B N4 C13B 116.9(10) . . ?
C11B N4 C13B 107.0(9) . . ?
C13A N4 C11A 116.4(9) . . ?
C14A N4 C11A 102.0(8) . . ?
C1 C6 C5 118.5(6) . . ?
C1 C6 C7 122.5(6) . . ?
C5 C6 C7 119.0(6) . . ?
O2 C8 N1 130.7(6) . . ?
O2 C8 O1 121.8(5) . . ?
N1 C8 O1 107.5(5) . . ?
N1 C9 N2 117.9(6) . . ?
N1 C9 N3B 122.9(7) . . ?
N2 C9 N3B 118.4(8) . . ?
N1 C9 N3A 123.6(7) . . ?
N2 C9 N3A 117.4(7) . . ?
C2 C1 C6 120.5(6) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C1 C2 C3 121.5(7) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C5 C6 120.1(6) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C4 C3 121.6(6) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
O1 C7 C6 111.2(5) . . ?
O1 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
O1 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C2 C3 C4 117.8(7) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C10A N3A C9 125.9(11) . . ?
C10A N3A HN3 121(5) . . ?
C9 N3A HN3 105(5) . . ?
O3A C10A N3A 125.5(13) . . ?
O3A C10A C11A 119.8(12) . . ?
N3A C10A C11A 113.5(11) . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C12A C11A C10A 112.5(11) . . ?
C12A C11A N4 116.2(10) . . ?
C10A C11A N4 104.2(9) . . ?
C12A C11A H11A 107.8 . . ?
C10A C11A H11A 107.8 . . ?
N4 C11A H11A 107.8 . . ?
N4 C13A H13A 109.5 . . ?
N4 C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
N4 C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
N4 C14A H14A 109.5 . . ?
N4 C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
N4 C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
O3B C10B N3B 123.7(13) . . ?
O3B C10B C11B 123.1(12) . . ?
N3B C10B C11B 113.2(11) . . ?
C9 N3B C10B 127.6(11) . . ?
C9 N3B HN3 111(5) . . ?
C10B N3B HN3 120(5) . . ?
N4 C11B C12B 112.7(11) . . ?
N4 C11B C10B 112.2(10) . . ?
C12B C11B C10B 111.7(12) . . ?
N4 C11B H11B 106.6 . . ?
C12B C11B H11B 106.6 . . ?
C10B C11B H11B 106.6 . . ?
N4 C13B H13D 109.5 . . ?
N4 C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
N4 C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
N4 C14B H14D 109.5 . . ?
N4 C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
N4 C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C11B C12B H12D 109.5 . . ?
C11B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C11B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?

_refine_diff_density_max         0.514
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.099

####################################################################### 
# 
# 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_2018NCS0156
_database_code_depnum_ccdc_archive 'CCDC 1952640'
loop_
_audit_author_name
_audit_author_address
'Jeppe Christensen '
;national crystallography service (southampton) and diamond light source (didcot)
United Kingdom
;
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 N4 O'
_chemical_formula_sum            'C15 H18 N4 O'
_chemical_formula_weight         270.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0032 0.0015 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0108 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   15.4703(10)
_cell_length_b                   5.1282(2)
_cell_length_c                   19.1266(13)
_cell_angle_alpha                90
_cell_angle_beta                 112.939(5)
_cell_angle_gamma                90
_cell_volume                     1397.41(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5584
_cell_measurement_theta_max      33.6607261706
_cell_measurement_theta_min      1.12420270486

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.007
_exptl_crystal_size_min          0.007
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_T_min  0.996
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CCP4 7.0.052: AIMLESS, version 0.6.2 : 15/01/18
Scaling & analysis of unmerged intensities,
absorption correction using spherical harmonics
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_dtime           0.004
_diffrn_detector_type            'Dectris, PILATUS 2M'
_diffrn_measurement_details      
;Data collection strategy using shutter-less operation of detector. 
Three omega scans -170 to 25 with phi 0, 120 and 240 respectively.
0.1 degree images with 0.5 sec exposure
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_details 'custom build fixed Chi diffractometer'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_radiation_collimation    'focusing mirrors and 0.100 mm pinhole'
_diffrn_radiation_monochromator  'Si 111, double crystal monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_source_type              'DLS beamline I19, undulator'
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_wavelength_determination estimated

_diffrn_radiation_wavelength_details 'Zr absorption edge'
_diffrn_reflns_number            19276
_diffrn_reflns_av_unetI/netI     0.1652
_diffrn_reflns_av_R_equivalents  0.1359
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.385
_diffrn_reflns_theta_max         26.573
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             6319
_reflns_number_gt                2831
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_max     0.971
_reflns_Friedel_fraction_full    0.975

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'GDA 8.44; generic data acquisition software'
_computing_cell_refinement       
'XIA2 0.4.0.438-g4431aaa, Winter, G. (2010) J. Appl. Cryst. 43'
_computing_data_reduction        
'XIA2 0.4.0.438-g4431aaa, Winter, G. (2010) J. Appl. Cryst. 43'
_computing_structure_solution    'SHELXT Acta Cryst. (2015). A71, 3-8'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0351P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 885 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.6(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         6319
_refine_ls_number_parameters     377
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1551
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.1584
_refine_ls_wR_factor_gt          0.1323
_refine_ls_goodness_of_fit_ref   0.861
_refine_ls_restrained_S_all      0.861
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.1390(3) 1.1519(7) 0.2886(2) 0.0494(10) Uani 1 1 d . . . . .
N2 N 0.5719(3) 0.4577(9) 0.2698(2) 0.0380(10) Uani 1 1 d . . . . .
O1 O 0.5670(3) 0.8870(7) 0.2403(2) 0.0512(10) Uani 1 1 d . . . . .
N8 N 0.2571(3) 0.9513(8) 0.4258(2) 0.0384(10) Uani 1 1 d . . . . .
N7 N 0.2582(3) 0.5176(8) 0.4275(2) 0.0397(10) Uani 1 1 d . . . . .
N3 N 0.4940(3) 0.2558(8) 0.3408(2) 0.0391(10) Uani 1 1 d . . . . .
N6 N 0.1705(3) 0.7211(9) 0.3092(2) 0.0405(11) Uani 1 1 d . . . . .
N4 N 0.4939(3) 0.6869(8) 0.3393(2) 0.0392(11) Uani 1 1 d . . . . .
N5 N 0.1145(3) 0.6593(8) 0.1529(2) 0.0429(11) Uani 1 1 d . . . . .
N1 N 0.7102(3) 0.3851(8) 0.2154(2) 0.0445(11) Uani 1 1 d . . . . .
C13 C 0.5214(3) 0.4653(10) 0.3158(3) 0.0367(11) Uani 1 1 d . . . . .
C28 C 0.2264(3) 0.7291(10) 0.3863(3) 0.0351(11) Uani 1 1 d . . . . .
C12 C 0.5921(3) 0.6659(10) 0.2349(3) 0.0406(13) Uani 1 1 d . . . . .
C14 C 0.4465(4) 0.3494(10) 0.3832(3) 0.0437(13) Uani 1 1 d . . . . .
H14 H 0.4189 0.2457 0.4087 0.052 Uiso 1 1 calc R U . . .
C27 C 0.1314(3) 0.9288(9) 0.2645(3) 0.0393(12) Uani 1 1 d . . . . .
C30 C 0.3137(4) 0.8764(10) 0.4985(3) 0.0425(13) Uani 1 1 d . . . . .
H30 H 0.3453 0.9850 0.5395 0.051 Uiso 1 1 calc R U . . .
C15 C 0.4455(4) 0.6141(10) 0.3828(3) 0.0427(13) Uani 1 1 d . . . . .
H15 H 0.4178 0.7232 0.4070 0.051 Uiso 1 1 calc R U . . .
C29 C 0.3138(4) 0.6132(10) 0.4981(3) 0.0431(13) Uani 1 1 d . . . . .
H29 H 0.3470 0.5099 0.5400 0.052 Uiso 1 1 calc R U . . .
C6 C 0.8510(4) 0.2446(12) 0.3276(3) 0.0533(15) Uani 1 1 d . . . . .
C16 C 0.3093(4) 0.3935(11) 0.1680(3) 0.0473(14) Uani 1 1 d . . . . .
H16 H 0.3196 0.4190 0.2188 0.057 Uiso 1 1 calc R U . . .
C11 C 0.6448(4) 0.6005(10) 0.1851(3) 0.0472(14) Uani 1 1 d . . . . .
H11 H 0.6799 0.7547 0.1809 0.057 Uiso 1 1 calc R U . . .
C26 C 0.0727(4) 0.8669(11) 0.1827(3) 0.0458(13) Uani 1 1 d . . . . .
H26 H 0.0666 1.0247 0.1523 0.055 Uiso 1 1 calc R U . . .
C21 C 0.2442(4) 0.5480(10) 0.1134(3) 0.0442(13) Uani 1 1 d . . . . .
C5 C 0.8155(4) 0.1242(12) 0.3752(4) 0.0577(16) Uani 1 1 d . . . . .
H5 H 0.7578 0.1762 0.3748 0.069 Uiso 1 1 calc R U . . .
C8 C 0.7231(4) 0.2754(11) 0.1503(3) 0.0568(16) Uani 1 1 d . . . . .
H8A H 0.7519 0.1042 0.1618 0.068 Uiso 1 1 calc R U . . .
H8B H 0.7615 0.3881 0.1335 0.068 Uiso 1 1 calc R U . . .
C22 C 0.1919(4) 0.7579(11) 0.1353(3) 0.0509(14) Uani 1 1 d . . . . .
H22A H 0.2353 0.8500 0.1792 0.061 Uiso 1 1 calc R U . . .
H22B H 0.1675 0.8821 0.0939 0.061 Uiso 1 1 calc R U . . .
C19 C 0.2806(4) 0.3172(11) 0.0185(3) 0.0546(16) Uani 1 1 d . . . . .
H19 H 0.2707 0.2911 -0.0321 0.065 Uiso 1 1 calc R U . . .
C1 C 0.9380(4) 0.1714(13) 0.3307(4) 0.0620(17) Uani 1 1 d . . . . .
H1 H 0.9636 0.2541 0.2999 0.074 Uiso 1 1 calc R U . . .
C23 C 0.0365(4) 0.5532(11) 0.0879(3) 0.0541(16) Uani 1 1 d . . . . .
H23A H 0.0518 0.3827 0.0740 0.065 Uiso 1 1 calc R U . . .
H23B H 0.0196 0.6685 0.0444 0.065 Uiso 1 1 calc R U . . .
C18 C 0.3451(4) 0.1639(11) 0.0751(4) 0.0555(16) Uani 1 1 d . . . . .
H18 H 0.3787 0.0348 0.0624 0.067 Uiso 1 1 calc R U . . .
C25 C -0.0263(4) 0.7658(13) 0.1698(3) 0.0581(15) Uani 1 1 d . . . . .
H25A H -0.0294 0.7118 0.2174 0.070 Uiso 1 1 calc R U . . .
H25B H -0.0731 0.8998 0.1470 0.070 Uiso 1 1 calc R U . . .
C7 C 0.7963(4) 0.4691(12) 0.2769(3) 0.0600(16) Uani 1 1 d . . . . .
H7A H 0.7808 0.5957 0.3079 0.072 Uiso 1 1 calc R U . . .
H7B H 0.8362 0.5550 0.2554 0.072 Uiso 1 1 calc R U . . .
C24 C -0.0418(4) 0.5355(11) 0.1166(4) 0.0615(17) Uani 1 1 d . . . . .
H24A H -0.0383 0.3726 0.1434 0.074 Uiso 1 1 calc R U . . .
H24B H -0.1026 0.5468 0.0749 0.074 Uiso 1 1 calc R U . . .
C10 C 0.5797(4) 0.5125(12) 0.1050(3) 0.0550(15) Uani 1 1 d . . . . .
H10A H 0.5166 0.4814 0.1023 0.066 Uiso 1 1 calc R U . . .
H10B H 0.5771 0.6434 0.0676 0.066 Uiso 1 1 calc R U . . .
C17 C 0.3587(4) 0.2048(12) 0.1495(3) 0.0519(14) Uani 1 1 d . . . . .
H17 H 0.4017 0.1034 0.1874 0.062 Uiso 1 1 calc R U . . .
C20 C 0.2319(4) 0.5071(11) 0.0384(3) 0.0545(15) Uani 1 1 d . . . . .
H20 H 0.1895 0.6109 0.0007 0.065 Uiso 1 1 calc R U . . .
C4 C 0.8649(5) -0.0727(14) 0.4233(3) 0.0654(17) Uani 1 1 d . . . . .
H4 H 0.8395 -0.1540 0.4544 0.078 Uiso 1 1 calc R U . . .
C2 C 0.9879(4) -0.0267(15) 0.3800(3) 0.0713(19) Uani 1 1 d . . . . .
H2 H 1.0466 -0.0753 0.3817 0.086 Uiso 1 1 calc R U . . .
C9 C 0.6238(5) 0.2590(13) 0.0914(3) 0.0653(17) Uani 1 1 d . . . . .
H9A H 0.5915 0.1070 0.0995 0.078 Uiso 1 1 calc R U . . .
H9B H 0.6229 0.2529 0.0405 0.078 Uiso 1 1 calc R U . . .
C3 C 0.9512(5) -0.1503(14) 0.4259(3) 0.0662(18) Uani 1 1 d . . . . .
H3 H 0.9841 -0.2841 0.4581 0.079 Uiso 1 1 calc R U . . .
HN6 H 0.167(3) 0.577(11) 0.293(3) 0.033(14) Uiso 1 1 d . . . . .
HN2 H 0.589(3) 0.302(11) 0.258(3) 0.037(14) Uiso 1 1 d . . . . .
HN4 H 0.501(3) 0.841(10) 0.325(3) 0.029(13) Uiso 1 1 d . . . . .
HN8 H 0.240(4) 1.122(13) 0.411(3) 0.065(19) 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 C27 1.222(6) . ?
N2 C12 1.359(6) . ?
N2 C13 1.386(6) . ?
N2 HN2 0.90(5) . ?
O1 C12 1.215(6) . ?
N8 C28 1.347(6) . ?
N8 C30 1.378(6) . ?
N8 HN8 0.93(6) . ?
N7 C28 1.318(6) . ?
N7 C29 1.378(6) . ?
N3 C13 1.312(6) . ?
N3 C14 1.376(6) . ?
N6 C27 1.352(6) . ?
N6 C28 1.390(6) . ?
N6 HN6 0.80(5) . ?
N4 C13 1.350(6) . ?
N4 C15 1.370(7) . ?
N4 HN4 0.86(5) . ?
N5 C22 1.455(7) . ?
N5 C23 1.459(7) . ?
N5 C26 1.470(6) . ?
N1 C8 1.448(7) . ?
N1 C11 1.457(7) . ?
N1 C7 1.458(7) . ?
C12 C11 1.514(8) . ?
C14 C15 1.358(7) . ?
C14 H14 0.9300 . ?
C27 C26 1.505(7) . ?
C30 C29 1.350(7) . ?
C30 H30 0.9300 . ?
C15 H15 0.9300 . ?
C29 H29 0.9300 . ?
C6 C1 1.376(8) . ?
C6 C5 1.378(8) . ?
C6 C7 1.530(8) . ?
C16 C17 1.363(8) . ?
C16 C21 1.383(8) . ?
C16 H16 0.9300 . ?
C11 C10 1.538(8) . ?
C11 H11 0.9800 . ?
C26 C25 1.544(8) . ?
C26 H26 0.9800 . ?
C21 C20 1.387(8) . ?
C21 C22 1.502(7) . ?
C5 C4 1.379(9) . ?
C5 H5 0.9300 . ?
C8 C9 1.512(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C19 C20 1.373(8) . ?
C19 C18 1.393(8) . ?
C19 H19 0.9300 . ?
C1 C2 1.396(9) . ?
C1 H1 0.9300 . ?
C23 C24 1.515(8) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C18 C17 1.371(8) . ?
C18 H18 0.9300 . ?
C25 C24 1.516(8) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C10 C9 1.537(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C17 H17 0.9300 . ?
C20 H20 0.9300 . ?
C4 C3 1.376(9) . ?
C4 H4 0.9300 . ?
C2 C3 1.373(9) . ?
C2 H2 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C3 H3 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
C12 N2 C13 125.7(5) . . ?
C12 N2 HN2 115(3) . . ?
C13 N2 HN2 119(3) . . ?
C28 N8 C30 106.1(4) . . ?
C28 N8 HN8 129(4) . . ?
C30 N8 HN8 124(4) . . ?
C28 N7 C29 103.8(4) . . ?
C13 N3 C14 104.5(4) . . ?
C27 N6 C28 126.0(5) . . ?
C27 N6 HN6 123(4) . . ?
C28 N6 HN6 111(4) . . ?
C13 N4 C15 106.8(4) . . ?
C13 N4 HN4 125(3) . . ?
C15 N4 HN4 128(3) . . ?
C22 N5 C23 114.4(4) . . ?
C22 N5 C26 111.3(4) . . ?
C23 N5 C26 104.9(4) . . ?
C8 N1 C11 105.1(4) . . ?
C8 N1 C7 114.8(5) . . ?
C11 N1 C7 111.8(4) . . ?
N3 C13 N4 112.4(4) . . ?
N3 C13 N2 123.4(5) . . ?
N4 C13 N2 124.3(5) . . ?
N7 C28 N8 113.2(4) . . ?
N7 C28 N6 122.9(4) . . ?
N8 C28 N6 123.9(4) . . ?
O1 C12 N2 123.3(5) . . ?
O1 C12 C11 121.9(5) . . ?
N2 C12 C11 114.8(5) . . ?
C15 C14 N3 110.7(5) . . ?
C15 C14 H14 124.7 . . ?
N3 C14 H14 124.7 . . ?
O2 C27 N6 123.1(5) . . ?
O2 C27 C26 121.3(4) . . ?
N6 C27 C26 115.5(4) . . ?
C29 C30 N8 105.9(5) . . ?
C29 C30 H30 127.0 . . ?
N8 C30 H30 127.0 . . ?
C14 C15 N4 105.6(5) . . ?
C14 C15 H15 127.2 . . ?
N4 C15 H15 127.2 . . ?
C30 C29 N7 111.1(5) . . ?
C30 C29 H29 124.4 . . ?
N7 C29 H29 124.4 . . ?
C1 C6 C5 118.9(6) . . ?
C1 C6 C7 121.5(6) . . ?
C5 C6 C7 119.5(5) . . ?
C17 C16 C21 121.8(5) . . ?
C17 C16 H16 119.1 . . ?
C21 C16 H16 119.1 . . ?
N1 C11 C12 112.3(4) . . ?
N1 C11 C10 104.9(4) . . ?
C12 C11 C10 112.8(4) . . ?
N1 C11 H11 108.9 . . ?
C12 C11 H11 108.9 . . ?
C10 C11 H11 108.9 . . ?
N5 C26 C27 112.2(4) . . ?
N5 C26 C25 104.7(4) . . ?
C27 C26 C25 113.3(4) . . ?
N5 C26 H26 108.8 . . ?
C27 C26 H26 108.8 . . ?
C25 C26 H26 108.8 . . ?
C16 C21 C20 117.5(5) . . ?
C16 C21 C22 120.8(5) . . ?
C20 C21 C22 121.7(5) . . ?
C6 C5 C4 120.7(6) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
N1 C8 C9 102.8(5) . . ?
N1 C8 H8A 111.2 . . ?
C9 C8 H8A 111.2 . . ?
N1 C8 H8B 111.2 . . ?
C9 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
N5 C22 C21 113.4(4) . . ?
N5 C22 H22A 108.9 . . ?
C21 C22 H22A 108.9 . . ?
N5 C22 H22B 108.9 . . ?
C21 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C20 C19 C18 119.3(6) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C6 C1 C2 120.2(6) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
N5 C23 C24 103.0(4) . . ?
N5 C23 H23A 111.2 . . ?
C24 C23 H23A 111.2 . . ?
N5 C23 H23B 111.2 . . ?
C24 C23 H23B 111.2 . . ?
H23A C23 H23B 109.1 . . ?
C17 C18 C19 119.5(5) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C24 C25 C26 104.9(5) . . ?
C24 C25 H25A 110.8 . . ?
C26 C25 H25A 110.8 . . ?
C24 C25 H25B 110.8 . . ?
C26 C25 H25B 110.8 . . ?
H25A C25 H25B 108.9 . . ?
N1 C7 C6 113.2(5) . . ?
N1 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C23 C24 C25 104.9(5) . . ?
C23 C24 H24A 110.8 . . ?
C25 C24 H24A 110.8 . . ?
C23 C24 H24B 110.8 . . ?
C25 C24 H24B 110.8 . . ?
H24A C24 H24B 108.8 . . ?
C9 C10 C11 104.8(5) . . ?
C9 C10 H10A 110.8 . . ?
C11 C10 H10A 110.8 . . ?
C9 C10 H10B 110.8 . . ?
C11 C10 H10B 110.8 . . ?
H10A C10 H10B 108.9 . . ?
C16 C17 C18 120.3(5) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C20 C21 121.6(6) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C3 C4 C5 120.8(6) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C3 C2 C1 120.7(6) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C8 C9 C10 102.5(5) . . ?
C8 C9 H9A 111.3 . . ?
C10 C9 H9A 111.3 . . ?
C8 C9 H9B 111.3 . . ?
C10 C9 H9B 111.3 . . ?
H9A C9 H9B 109.2 . . ?
C2 C3 C4 118.8(6) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_2017NCS0802
_database_code_depnum_ccdc_archive 'CCDC 1952641'
loop_
_audit_author_name
_audit_author_address
'Jeppe Christensen '
;national crystallography service (southampton) and diamond light source (didcot)
United Kingdom
;
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 N3 O'
_chemical_formula_sum            'C11 H15 N3 O'
_chemical_formula_weight         205.26

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.88050(10)
_cell_length_b                   12.7554(2)
_cell_length_c                   17.4319(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2196.94(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4519
_cell_measurement_theta_min      5.6500
_cell_measurement_theta_max      69.6190

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.663
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_T_min  0.83306
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC11 quarter χ goniometer'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_radiation_collimation    'Varimax focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'Rotating anode'
_diffrn_source_type              'Rigaku 007 HF'
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_source_current           30.0
_diffrn_source_target            Cu
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1058856000
_diffrn_orient_matrix_UB_12      -0.0831146000
_diffrn_orient_matrix_UB_13      -0.0225389000
_diffrn_orient_matrix_UB_21      -0.0764603000
_diffrn_orient_matrix_UB_22      0.0825051000
_diffrn_orient_matrix_UB_23      -0.0476676000
_diffrn_orient_matrix_UB_31      0.0852585000
_diffrn_orient_matrix_UB_32      -0.0292788000
_diffrn_orient_matrix_UB_33      -0.0709424000
_diffrn_measurement_details      
;
Data collection strategy using shutter-less operation of detector. 

List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -162.00-137.00   0.50    1.76    --  -90.00   0.00   0.00   50
  2  ω    -33.00  -7.00   0.50    1.76    --  -90.00   0.00   0.00   52
  3  ω    -55.00 -15.00   0.50    1.76    --  -90.00  37.00 -24.00   80
  4  ω   -112.00 -63.00   0.50    1.76    --  -90.00  37.00 -24.00   98
  5  ω   -177.00-152.00   0.50    1.76    --  -90.00  37.00 -24.00   50
  6  ω   -179.00-148.00   0.50    1.76    --  -90.00  43.00  90.00   62
  7  ω   -119.00 -90.00   0.50    1.76    --  -90.00  43.00  90.00   58
  8  ω    -66.00 -41.00   0.50    1.76    --  -90.00  43.00  90.00   50
  9  ω    -44.00 -18.00   0.50    1.76    --  -90.00  57.00 125.00   52
 10  ω   -179.00-107.00   0.50    1.76    --  -90.00  57.00 125.00  144
 11  ω   -139.00 -17.00   0.50    1.76    --  -90.00  57.00-150.00  244
 12  ω   -154.00  -1.00   0.50    1.76    --  -90.00  60.00-180.00  306
 13  ω     30.00  65.00   0.50    0.50    --    0.00  57.00 125.00   70
 14  ω    -88.00  12.00   0.50    0.50    --    0.00  57.00 125.00  200
 15  ω     35.00  61.00   0.50    1.76    --    5.00  37.00 -24.00   52
;
_diffrn_reflns_number            6642
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.074
_diffrn_reflns_theta_max         69.739
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2053
_reflns_number_gt                1973
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0580P)²+1.7731P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 819 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(11)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2053
_refine_ls_number_parameters     141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1094
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5688(2) 0.69763(16) 0.61938(12) 0.0334(5) Uani 1 1 d . . . . .
N2 N 0.3936(2) 0.62296(17) 0.55362(13) 0.0214(5) Uani 1 1 d . . . . .
N3 N 0.2662(2) 0.48243(17) 0.59543(11) 0.0236(5) Uani 1 1 d . . . . .
C7 C 0.3319(2) 0.56941(19) 0.61574(14) 0.0205(5) Uani 1 1 d . . . . .
C6 C 0.5053(3) 0.68475(19) 0.55936(15) 0.0249(6) Uani 1 1 d . . . . .
C8 C 0.3390(3) 0.6061(2) 0.69093(15) 0.0253(6) Uani 1 1 d . . . . .
H8 H 0.3877 0.6682 0.7031 0.030 Uiso 1 1 calc R U . . .
N1 N 0.4920(3) 0.6992(2) 0.41786(14) 0.0372(6) Uani 1 1 d . . . . .
C11 C 0.2027(3) 0.4288(2) 0.65135(15) 0.0288(6) Uani 1 1 d . . . . .
H11 H 0.1552 0.3667 0.6379 0.035 Uiso 1 1 calc R U . . .
C5 C 0.5468(3) 0.7430(2) 0.48756(17) 0.0285(6) Uani 1 1 d . . . . .
H5 H 0.6478 0.7444 0.4841 0.034 Uiso 1 1 calc R U . . .
C9 C 0.2732(3) 0.5498(2) 0.74704(16) 0.0289(6) Uani 1 1 d . . . . .
H9 H 0.2760 0.5728 0.7989 0.035 Uiso 1 1 calc R U . . .
C10 C 0.2030(3) 0.4596(2) 0.72776(15) 0.0304(6) Uani 1 1 d . . . . .
H10 H 0.1564 0.4201 0.7656 0.036 Uiso 1 1 calc R U . . .
C2 C 0.4689(3) 0.7860(3) 0.36433(17) 0.0389(8) Uani 1 1 d . . . . .
H2A H 0.4033 0.7663 0.3239 0.047 Uiso 1 1 calc R U . . .
H2B H 0.5544 0.8090 0.3400 0.047 Uiso 1 1 calc R U . . .
C4 C 0.4921(3) 0.8579(2) 0.49088(18) 0.0360(7) Uani 1 1 d . . . . .
H4A H 0.4337 0.8681 0.5364 0.043 Uiso 1 1 calc R U . . .
H4B H 0.5676 0.9088 0.4930 0.043 Uiso 1 1 calc R U . . .
C3 C 0.4111(3) 0.8712(3) 0.4174(2) 0.0417(8) Uani 1 1 d . . . . .
H3A H 0.4247 0.9419 0.3952 0.050 Uiso 1 1 calc R U . . .
H3B H 0.3133 0.8601 0.4267 0.050 Uiso 1 1 calc R U . . .
C1 C 0.5773(4) 0.6186(3) 0.3860(2) 0.0546(10) Uani 1 1 d . . . . .
H1A H 0.6663 0.6481 0.3739 0.082 Uiso 1 1 calc R U . . .
H1B H 0.5359 0.5911 0.3391 0.082 Uiso 1 1 calc R U . . .
H1C H 0.5877 0.5617 0.4234 0.082 Uiso 1 1 calc R U . . .
HN2 H 0.367(3) 0.609(3) 0.507(2) 0.035(9) 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
O1 C6 1.231(3) . ?
N2 C6 1.359(4) . ?
N2 C7 1.418(3) . ?
N2 HN2 0.88(4) . ?
N3 C7 1.333(3) . ?
N3 C11 1.346(3) . ?
C7 C8 1.394(4) . ?
C6 C5 1.512(4) . ?
C8 C9 1.377(4) . ?
C8 H8 0.9500 . ?
N1 C1 1.441(4) . ?
N1 C5 1.443(4) . ?
N1 C2 1.465(4) . ?
C11 C10 1.389(4) . ?
C11 H11 0.9500 . ?
C5 C4 1.563(4) . ?
C5 H5 1.0000 . ?
C9 C10 1.385(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C2 C3 1.537(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C4 C3 1.520(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N2 C7 124.9(2) . . ?
C6 N2 HN2 115(2) . . ?
C7 N2 HN2 119(2) . . ?
C7 N3 C11 117.2(2) . . ?
N3 C7 C8 123.6(2) . . ?
N3 C7 N2 114.0(2) . . ?
C8 C7 N2 122.3(2) . . ?
O1 C6 N2 123.6(2) . . ?
O1 C6 C5 119.9(2) . . ?
N2 C6 C5 116.4(2) . . ?
C9 C8 C7 118.0(2) . . ?
C9 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
C1 N1 C5 112.4(3) . . ?
C1 N1 C2 112.6(3) . . ?
C5 N1 C2 107.6(2) . . ?
N3 C11 C10 123.4(3) . . ?
N3 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
N1 C5 C6 113.9(2) . . ?
N1 C5 C4 105.3(2) . . ?
C6 C5 C4 109.6(2) . . ?
N1 C5 H5 109.3 . . ?
C6 C5 H5 109.3 . . ?
C4 C5 H5 109.3 . . ?
C8 C9 C10 119.8(3) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C11 118.0(3) . . ?
C9 C10 H10 121.0 . . ?
C11 C10 H10 121.0 . . ?
N1 C2 C3 102.0(2) . . ?
N1 C2 H2A 111.4 . . ?
C3 C2 H2A 111.4 . . ?
N1 C2 H2B 111.4 . . ?
C3 C2 H2B 111.4 . . ?
H2A C2 H2B 109.2 . . ?
C3 C4 C5 104.8(3) . . ?
C3 C4 H4A 110.8 . . ?
C5 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
C5 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
C4 C3 C2 103.5(3) . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
C2 C3 H3B 111.1 . . ?
H3A C3 H3B 109.0 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_refine_diff_density_max         0.440
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.044

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

data_shelx_CCDC9
_database_code_depnum_ccdc_archive 'CCDC 1952639'
loop_
_audit_author_name
_audit_author_address
'Jeppe Christensen '
;national crystallography service (southampton) and diamond light source (didcot)
United Kingdom
;
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C15 H20 N4 O), H2 O'
_chemical_formula_sum            'C30 H42 N8 O3'
_chemical_formula_weight         562.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   12.0576(2)
_cell_length_b                   11.3774(2)
_cell_length_c                   11.1889(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1534.94(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    33986
_cell_measurement_theta_min      2.4040
_cell_measurement_theta_max      29.8020

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             604
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_T_min  0.91544
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_collimation    '0.07 mm Confocal mirrors, HF Varimax'
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_source                   'rotating anode'
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source_target            Mo
_diffrn_source_type              'FR-E+ SuperBright rotating anode'
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12'
_diffrn_measurement_method       'profile data from ω scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 14.286
_diffrn_reflns_number            54936
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.461
_diffrn_reflns_theta_max         29.970
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4257
_reflns_number_gt                3971
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_max     0.932
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    
'SHELXT (G. M. Sheldrick Acta Cryst. (2015). A71, 3-8)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0564P)²+0.2757P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4257
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0998
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.5000 0.5000 0.28210(18) 0.0254(4) Uani 1 2 d S T P . .
O1 O 0.08456(10) 0.60243(11) 0.24783(13) 0.0297(3) Uani 1 1 d . . . . .
N2 N 0.25967(11) 0.53003(11) 0.26943(13) 0.0201(3) Uani 1 1 d . . . . .
N3 N 0.14509(11) 0.37462(12) 0.19141(13) 0.0186(3) Uani 1 1 d . . . . .
N4 N 0.33082(11) 0.35646(11) 0.18288(13) 0.0195(3) Uani 1 1 d . . . . .
N1 N 0.33233(11) 0.71553(13) 0.38836(13) 0.0229(3) Uani 1 1 d . . . . .
C8 C 0.18092(13) 0.61508(15) 0.27876(15) 0.0220(3) Uani 1 1 d . . . . .
C9 C 0.24594(12) 0.42171(13) 0.21595(13) 0.0183(3) Uani 1 1 d . . . . .
C15 C 0.28192(13) 0.25729(13) 0.13277(14) 0.0188(3) Uani 1 1 d . . . . .
C10 C 0.16572(13) 0.26725(13) 0.13712(14) 0.0183(3) Uani 1 1 d . . . . .
C14 C 0.33079(14) 0.15773(15) 0.08297(15) 0.0221(3) Uani 1 1 d . . . . .
H14 H 0.4091 0.1497 0.0791 0.026 Uiso 1 1 calc R U . . .
C13 C 0.26116(15) 0.07081(14) 0.03927(15) 0.0253(3) Uani 1 1 d . . . . .
H13 H 0.2926 0.0019 0.0054 0.030 Uiso 1 1 calc R U . . .
C12 C 0.14525(15) 0.08206(15) 0.04382(15) 0.0254(3) Uani 1 1 d . . . . .
H12 H 0.1001 0.0209 0.0126 0.030 Uiso 1 1 calc R U . . .
C11 C 0.09538(14) 0.18061(14) 0.09291(16) 0.0229(3) Uani 1 1 d . . . . .
H11 H 0.0170 0.1886 0.0962 0.027 Uiso 1 1 calc R U . . .
C6 C 0.24582(16) 0.81854(15) 0.22323(18) 0.0302(4) Uani 1 1 d . . . . .
H6A H 0.2130 0.7891 0.1478 0.036 Uiso 1 1 calc R U . . .
H6B H 0.2142 0.8969 0.2414 0.036 Uiso 1 1 calc R U . . .
C7 C 0.22485(13) 0.73128(14) 0.32747(16) 0.0232(3) Uani 1 1 d . . . . .
H7 H 0.1698 0.7657 0.3844 0.028 Uiso 1 1 calc R U . . .
C5 C 0.37129(17) 0.82411(17) 0.21470(19) 0.0347(4) Uani 1 1 d . . . . .
H5A H 0.4005 0.7606 0.1631 0.042 Uiso 1 1 calc R U . . .
H5B H 0.3961 0.9009 0.1829 0.042 Uiso 1 1 calc R U . . .
C4 C 0.40771(15) 0.80785(16) 0.34318(19) 0.0311(4) Uani 1 1 d . . . . .
H4A H 0.4860 0.7821 0.3475 0.037 Uiso 1 1 calc R U . . .
H4B H 0.3990 0.8816 0.3892 0.037 Uiso 1 1 calc R U . . .
C3 C 0.32643(16) 0.70564(18) 0.51863(17) 0.0303(4) Uani 1 1 d . . . . .
H3 H 0.2952 0.7803 0.5516 0.036 Uiso 1 1 calc R U . . .
C2 C 0.2521(2) 0.6042(2) 0.55628(17) 0.0400(5) Uani 1 1 d . . . . .
H2A H 0.1772 0.6165 0.5246 0.060 Uiso 1 1 calc R U . . .
H2B H 0.2490 0.6002 0.6437 0.060 Uiso 1 1 calc R U . . .
H2C H 0.2821 0.5303 0.5248 0.060 Uiso 1 1 calc R U . . .
C1 C 0.44294(18) 0.6891(2) 0.5675(2) 0.0434(5) Uani 1 1 d . . . . .
H1A H 0.4793 0.6242 0.5252 0.065 Uiso 1 1 calc R U . . .
H1B H 0.4391 0.6710 0.6530 0.065 Uiso 1 1 calc R U . . .
H1C H 0.4856 0.7615 0.5557 0.065 Uiso 1 1 calc R U . . .
H2N H 0.327(2) 0.545(2) 0.296(2) 0.035(6) Uiso 1 1 d . . . . .
H3N H 0.080(2) 0.405(2) 0.211(2) 0.035(6) Uiso 1 1 d . . . . .
H2O H 0.471(3) 0.450(3) 0.238(3) 0.064(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 H2O 0.82(3) . ?
O1 C8 1.221(2) . ?
N2 C8 1.360(2) . ?
N2 C9 1.3799(19) . ?
N2 H2N 0.88(3) . ?
N3 C9 1.3570(19) . ?
N3 C10 1.387(2) . ?
N3 H3N 0.89(3) . ?
N4 C9 1.317(2) . ?
N4 C15 1.3911(19) . ?
N1 C3 1.464(2) . ?
N1 C7 1.475(2) . ?
N1 C4 1.478(2) . ?
C8 C7 1.525(2) . ?
C15 C14 1.393(2) . ?
C15 C10 1.406(2) . ?
C10 C11 1.391(2) . ?
C14 C13 1.386(2) . ?
C14 H14 0.9500 . ?
C13 C12 1.404(3) . ?
C13 H13 0.9500 . ?
C12 C11 1.386(2) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?
C6 C5 1.517(3) . ?
C6 C7 1.552(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7 1.0000 . ?
C5 C4 1.514(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C3 C1 1.519(3) . ?
C3 C2 1.521(3) . ?
C3 H3 1.0000 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N2 C9 125.81(13) . . ?
C8 N2 H2N 118.7(16) . . ?
C9 N2 H2N 115.4(16) . . ?
C9 N3 C10 106.00(13) . . ?
C9 N3 H3N 126.0(16) . . ?
C10 N3 H3N 127.9(16) . . ?
C9 N4 C15 103.94(13) . . ?
C3 N1 C7 115.25(14) . . ?
C3 N1 C4 115.16(14) . . ?
C7 N1 C4 107.22(14) . . ?
O1 C8 N2 123.99(15) . . ?
O1 C8 C7 122.28(15) . . ?
N2 C8 C7 113.69(13) . . ?
N4 C9 N3 114.64(14) . . ?
N4 C9 N2 122.14(14) . . ?
N3 C9 N2 123.22(14) . . ?
N4 C15 C14 129.89(15) . . ?
N4 C15 C10 110.06(13) . . ?
C14 C15 C10 120.05(14) . . ?
N3 C10 C11 132.11(15) . . ?
N3 C10 C15 105.36(13) . . ?
C11 C10 C15 122.54(14) . . ?
C13 C14 C15 117.70(15) . . ?
C13 C14 H14 121.1 . . ?
C15 C14 H14 121.1 . . ?
C14 C13 C12 121.66(15) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C11 C12 C13 121.33(15) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C11 C10 116.73(15) . . ?
C12 C11 H11 121.6 . . ?
C10 C11 H11 121.6 . . ?
C5 C6 C7 103.67(15) . . ?
C5 C6 H6A 111.0 . . ?
C7 C6 H6A 111.0 . . ?
C5 C6 H6B 111.0 . . ?
C7 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
N1 C7 C8 111.40(13) . . ?
N1 C7 C6 106.36(14) . . ?
C8 C7 C6 110.02(14) . . ?
N1 C7 H7 109.7 . . ?
C8 C7 H7 109.7 . . ?
C6 C7 H7 109.7 . . ?
C4 C5 C6 102.96(16) . . ?
C4 C5 H5A 111.2 . . ?
C6 C5 H5A 111.2 . . ?
C4 C5 H5B 111.2 . . ?
C6 C5 H5B 111.2 . . ?
H5A C5 H5B 109.1 . . ?
N1 C4 C5 103.48(14) . . ?
N1 C4 H4A 111.1 . . ?
C5 C4 H4A 111.1 . . ?
N1 C4 H4B 111.1 . . ?
C5 C4 H4B 111.1 . . ?
H4A C4 H4B 109.0 . . ?
N1 C3 C1 108.83(16) . . ?
N1 C3 C2 111.28(15) . . ?
C1 C3 C2 110.58(19) . . ?
N1 C3 H3 108.7 . . ?
C1 C3 H3 108.7 . . ?
C2 C3 H3 108.7 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.040

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

data_shelx_CCDC10
_database_code_depnum_ccdc_archive 'CCDC 1952642'
loop_
_audit_author_name
_audit_author_address
'Jeppe Christensen '
;national crystallography service (southampton) and diamond light source (didcot)
United Kingdom
;
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H31 N5 O2'
_chemical_formula_sum            'C25 H31 N5 O2'
_chemical_formula_weight         433.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.83130(10)
_cell_length_b                   9.9682(2)
_cell_length_c                   34.4021(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2342.64(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    32332
_cell_measurement_theta_min      2.1280
_cell_measurement_theta_max      29.8480

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_T_min  0.82829
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_collimation    '0.07 mm Confocal mirrors, HF Varimax'
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_source                   'rotating anode'
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source_target            Mo
_diffrn_source_type              'FR-E+ SuperBright rotating anode'
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12'
_diffrn_measurement_method       'profile data from ω scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 14.286
_diffrn_reflns_number            75609
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_av_R_equivalents  0.0842
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_theta_min         2.361
_diffrn_reflns_theta_max         29.919
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6573
_reflns_number_gt                5708
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_max     0.951
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_cell_refinement       
'CrysalisPRO 171.38.43 (Rigaku Oxford Diffraction 2015)'
_computing_data_reduction        
'CrysalisPRO 171.38.43 (Rigaku Oxford Diffraction 2015)'
_computing_structure_solution    
'SHELXT (G. M. Sheldrick Acta Cryst. (2015). A71, 3-8)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0596P)²+0.6582P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2089 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration unk
_refine_ls_number_reflns         6573
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1189
_refine_ls_wR_factor_gt          0.1135
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 1.2969(2) 0.60404(17) 0.59237(5) 0.0287(4) Uani 1 1 d . . . . .
N2 N 0.9966(2) 0.29853(17) 0.65416(5) 0.0183(3) Uani 1 1 d . . . . .
N4 N 1.0216(3) 0.48891(17) 0.61172(5) 0.0185(3) Uani 1 1 d . . . . .
N5 N 0.8212(3) 0.61425(16) 0.55050(5) 0.0175(3) Uani 1 1 d . . . . .
N1 N 0.5128(3) 0.20843(17) 0.69130(5) 0.0192(3) Uani 1 1 d . . . . .
N3 N 1.2950(3) 0.39036(19) 0.63989(6) 0.0238(4) Uani 1 1 d . . . . .
O2 O 0.6972(3) 0.40449(19) 0.64500(7) 0.0496(6) Uani 1 1 d . . . . .
C13 C 1.1030(3) 0.3917(2) 0.63586(6) 0.0177(4) Uani 1 1 d . . . . .
C6 C 0.3451(3) 0.2786(2) 0.75206(6) 0.0243(5) Uani 1 1 d . . . . .
C20 C 0.7115(3) 0.46488(18) 0.49659(6) 0.0202(4) Uani 1 1 d . . . . .
C19 C 0.8814(3) 0.5308(2) 0.51748(6) 0.0210(4) Uani 1 1 d . . . . .
H19A H 0.9715 0.4601 0.5269 0.025 Uiso 1 1 calc R U . . .
H19B H 0.9544 0.5872 0.4987 0.025 Uiso 1 1 calc R U . . .
C14 C 1.1206(3) 0.5880(2) 0.59144(6) 0.0190(4) Uani 1 1 d . . . . .
C12 C 0.7988(3) 0.3086(2) 0.65588(6) 0.0218(4) Uani 1 1 d . . . . .
C8 C 0.4078(3) 0.0786(2) 0.69080(6) 0.0225(4) Uani 1 1 d . . . . .
H8A H 0.2644 0.0923 0.6920 0.027 Uiso 1 1 calc R U . . .
H8B H 0.4486 0.0214 0.7129 0.027 Uiso 1 1 calc R U . . .
C18 C 0.6921(3) 0.72571(19) 0.53917(6) 0.0216(4) Uani 1 1 d . . . . .
H18A H 0.5574 0.6933 0.5343 0.026 Uiso 1 1 calc R U . . .
H18B H 0.7415 0.7707 0.5155 0.026 Uiso 1 1 calc R U . . .
C25 C 0.5455(3) 0.4208(2) 0.51639(7) 0.0220(4) Uani 1 1 d . . . . .
H25 H 0.5341 0.4359 0.5436 0.026 Uiso 1 1 calc R U . . .
C15 C 0.9891(3) 0.68188(19) 0.56864(6) 0.0193(4) Uani 1 1 d . . . . .
H15 H 1.0680 0.7273 0.5480 0.023 Uiso 1 1 calc R U . . .
C21 C 0.7250(4) 0.4427(2) 0.45671(6) 0.0248(4) Uani 1 1 d . . . . .
H21 H 0.8365 0.4738 0.4429 0.030 Uiso 1 1 calc R U . . .
C23 C 0.4123(4) 0.3311(2) 0.45694(8) 0.0291(5) Uani 1 1 d . . . . .
H23 H 0.3113 0.2846 0.4436 0.035 Uiso 1 1 calc R U . . .
C5 C 0.2165(4) 0.3829(2) 0.74294(6) 0.0254(4) Uani 1 1 d . . . . .
H5 H 0.2513 0.4456 0.7233 0.030 Uiso 1 1 calc R U . . .
C24 C 0.3963(3) 0.3547(2) 0.49652(7) 0.0263(5) Uani 1 1 d . . . . .
H24 H 0.2831 0.3257 0.5102 0.032 Uiso 1 1 calc R U . . .
C17 C 0.6968(4) 0.8207(2) 0.57384(7) 0.0283(5) Uani 1 1 d . . . . .
H17A H 0.5844 0.8040 0.5913 0.034 Uiso 1 1 calc R U . . .
H17B H 0.6929 0.9153 0.5651 0.034 Uiso 1 1 calc R U . . .
C11 C 0.7037(3) 0.1831(2) 0.67277(7) 0.0247(4) Uani 1 1 d . . . . .
H11 H 0.7944 0.1400 0.6919 0.030 Uiso 1 1 calc R U . . .
C4 C 0.0384(4) 0.3965(3) 0.76213(7) 0.0330(5) Uani 1 1 d . . . . .
H4 H -0.0473 0.4680 0.7556 0.040 Uiso 1 1 calc R U . . .
C22 C 0.5766(4) 0.3755(2) 0.43686(7) 0.0287(5) Uani 1 1 d . . . . .
H22 H 0.5877 0.3600 0.4097 0.034 Uiso 1 1 calc R U . . .
C16 C 0.8917(4) 0.7893(2) 0.59450(7) 0.0266(5) Uani 1 1 d . . . . .
H16A H 0.8683 0.7543 0.6210 0.032 Uiso 1 1 calc R U . . .
H16B H 0.9746 0.8706 0.5963 0.032 Uiso 1 1 calc R U . . .
C7 C 0.5380(3) 0.2630(2) 0.73087(7) 0.0257(5) Uani 1 1 d . . . . .
H7A H 0.6031 0.3516 0.7292 0.031 Uiso 1 1 calc R U . . .
H7B H 0.6242 0.2025 0.7459 0.031 Uiso 1 1 calc R U . . .
C1 C 0.2898(4) 0.1885(2) 0.78118(7) 0.0330(5) Uani 1 1 d . . . . .
H1 H 0.3757 0.1176 0.7882 0.040 Uiso 1 1 calc R U . . .
C2 C 0.1106(5) 0.2012(3) 0.79999(7) 0.0400(7) Uani 1 1 d . . . . .
H2 H 0.0738 0.1377 0.8192 0.048 Uiso 1 1 calc R U . . .
C3 C -0.0144(4) 0.3056(3) 0.79091(8) 0.0378(6) Uani 1 1 d . . . . .
H3 H -0.1355 0.3151 0.8042 0.045 Uiso 1 1 calc R U . . .
C9 C 0.4675(4) 0.0158(3) 0.65210(8) 0.0390(6) Uani 1 1 d . . . . .
H9A H 0.4881 -0.0819 0.6551 0.047 Uiso 1 1 calc R U . . .
H9B H 0.3645 0.0306 0.6323 0.047 Uiso 1 1 calc R U . . .
C10 C 0.6534(5) 0.0830(3) 0.64021(11) 0.0574(10) Uani 1 1 d . . . . .
H10A H 0.6358 0.1305 0.6152 0.069 Uiso 1 1 calc R U . . .
H10B H 0.7595 0.0161 0.6372 0.069 Uiso 1 1 calc R U . . .
H12 H 1.365(5) 0.449(3) 0.6264(9) 0.042(9) Uiso 1 1 d . . . . .
H14 H 0.892(5) 0.488(3) 0.6095(8) 0.042(9) Uiso 1 1 d . . . . .
H13 H 1.350(4) 0.330(3) 0.6551(9) 0.040(8) 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
O3 C14 1.216(3) . ?
N2 C13 1.337(3) . ?
N2 C12 1.357(2) . ?
N4 C14 1.386(3) . ?
N4 C13 1.392(3) . ?
N4 H14 0.89(3) . ?
N5 C19 1.467(3) . ?
N5 C15 1.469(3) . ?
N5 C18 1.471(3) . ?
N1 C11 1.473(3) . ?
N1 C7 1.476(3) . ?
N1 C8 1.480(3) . ?
N3 C13 1.319(3) . ?
N3 H12 0.88(3) . ?
N3 H13 0.88(3) . ?
O2 C12 1.239(3) . ?
C6 C5 1.397(3) . ?
C6 C1 1.398(3) . ?
C6 C7 1.514(3) . ?
C20 C21 1.393(3) . ?
C20 C25 1.394(3) . ?
C20 C19 1.515(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C14 C15 1.516(3) . ?
C12 C11 1.525(3) . ?
C8 C9 1.526(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C18 C17 1.523(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C25 C24 1.393(3) . ?
C25 H25 0.9500 . ?
C15 C16 1.543(3) . ?
C15 H15 1.0000 . ?
C21 C22 1.394(3) . ?
C21 H21 0.9500 . ?
C23 C24 1.386(4) . ?
C23 C22 1.390(4) . ?
C23 H23 0.9500 . ?
C5 C4 1.391(3) . ?
C5 H5 0.9500 . ?
C24 H24 0.9500 . ?
C17 C16 1.542(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C11 C10 1.539(4) . ?
C11 H11 1.0000 . ?
C4 C3 1.390(4) . ?
C4 H4 0.9500 . ?
C22 H22 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C1 C2 1.390(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.382(4) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C9 C10 1.493(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N2 C12 120.70(18) . . ?
C14 N4 C13 127.03(18) . . ?
C14 N4 H14 117(2) . . ?
C13 N4 H14 116(2) . . ?
C19 N5 C15 111.74(16) . . ?
C19 N5 C18 113.04(16) . . ?
C15 N5 C18 103.52(15) . . ?
C11 N1 C7 111.04(17) . . ?
C11 N1 C8 105.90(16) . . ?
C7 N1 C8 112.94(17) . . ?
C13 N3 H12 118(2) . . ?
C13 N3 H13 119(2) . . ?
H12 N3 H13 122(3) . . ?
N3 C13 N2 118.96(19) . . ?
N3 C13 N4 117.80(19) . . ?
N2 C13 N4 123.22(18) . . ?
C5 C6 C1 118.0(2) . . ?
C5 C6 C7 121.0(2) . . ?
C1 C6 C7 121.0(2) . . ?
C21 C20 C25 119.0(2) . . ?
C21 C20 C19 119.1(2) . . ?
C25 C20 C19 121.89(19) . . ?
N5 C19 C20 113.49(17) . . ?
N5 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
N5 C19 H19B 108.9 . . ?
C20 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
O3 C14 N4 124.3(2) . . ?
O3 C14 C15 121.34(19) . . ?
N4 C14 C15 114.29(18) . . ?
O2 C12 N2 127.03(19) . . ?
O2 C12 C11 120.61(19) . . ?
N2 C12 C11 112.35(18) . . ?
N1 C8 C9 103.82(18) . . ?
N1 C8 H8A 111.0 . . ?
C9 C8 H8A 111.0 . . ?
N1 C8 H8B 111.0 . . ?
C9 C8 H8B 111.0 . . ?
H8A C8 H8B 109.0 . . ?
N5 C18 C17 104.45(17) . . ?
N5 C18 H18A 110.9 . . ?
C17 C18 H18A 110.9 . . ?
N5 C18 H18B 110.9 . . ?
C17 C18 H18B 110.9 . . ?
H18A C18 H18B 108.9 . . ?
C24 C25 C20 120.3(2) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 119.8 . . ?
N5 C15 C14 113.54(16) . . ?
N5 C15 C16 103.13(17) . . ?
C14 C15 C16 112.67(17) . . ?
N5 C15 H15 109.1 . . ?
C14 C15 H15 109.1 . . ?
C16 C15 H15 109.1 . . ?
C20 C21 C22 120.7(2) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C24 C23 C22 119.8(2) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C23 C24 C25 120.3(2) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C18 C17 C16 104.67(18) . . ?
C18 C17 H17A 110.8 . . ?
C16 C17 H17A 110.8 . . ?
C18 C17 H17B 110.8 . . ?
C16 C17 H17B 110.8 . . ?
H17A C17 H17B 108.9 . . ?
N1 C11 C12 113.66(17) . . ?
N1 C11 C10 103.22(19) . . ?
C12 C11 C10 110.5(2) . . ?
N1 C11 H11 109.8 . . ?
C12 C11 H11 109.8 . . ?
C10 C11 H11 109.8 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C23 C22 C21 119.8(2) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C17 C16 C15 104.29(17) . . ?
C17 C16 H16A 110.9 . . ?
C15 C16 H16A 110.9 . . ?
C17 C16 H16B 110.9 . . ?
C15 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
N1 C7 C6 112.36(17) . . ?
N1 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C2 C1 C6 120.9(2) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C10 C9 C8 106.4(2) . . ?
C10 C9 H9A 110.4 . . ?
C8 C9 H9A 110.4 . . ?
C10 C9 H9B 110.4 . . ?
C8 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
C9 C10 C11 106.3(2) . . ?
C9 C10 H10A 110.5 . . ?
C11 C10 H10A 110.5 . . ?
C9 C10 H10B 110.5 . . ?
C11 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_2018NCS0072
_database_code_depnum_ccdc_archive 'CCDC 1952648'
loop_
_audit_author_name
_audit_author_address
'Jeppe Christensen '
;national crystallography service (southampton) and diamond light source (didcot)
United Kingdom
;
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H45 N8 O2'
_chemical_formula_weight         621.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0010 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.4470(4)
_cell_length_b                   12.0122(5)
_cell_length_c                   24.2818(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.043(2)
_cell_angle_gamma                90
_cell_volume                     3550.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    35(2)
_cell_measurement_reflns_used    2202
_cell_measurement_theta_max      21.0818251411
_cell_measurement_theta_min      1.66994203036

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_F_000             1332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.064
_exptl_crystal_size_mid          0.014
_exptl_crystal_size_min          0.014
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CCP4 7.0.048: AIMLESS, version 0.5.32 : 29/03/17
Scaling & analysis of unmerged intensities, 
absorption correction using spherical harmonics
;
_diffrn_ambient_temperature      35(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_dtime           0.004
_diffrn_detector_type            'Dectris, PILATUS 2M'
_diffrn_measurement_details      
;Data collection strategy using shutter-less operation of detector. 
Three omega scans -170 to 25 with phi 0, 120 and 240 respectively.
0.1 degree images with 0.5 sec exposure
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_details 'custom build fixed Chi diffractometer'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_radiation_collimation    'focusing mirrors and 0.100 mm pinhole'
_diffrn_radiation_monochromator  'Si 111, double crystal monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_source_type              'DLS beamline I19, undulator'
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_wavelength_determination estimated

_diffrn_radiation_wavelength_details 'Zr absorption edge'
_diffrn_reflns_number            14653
_diffrn_reflns_av_unetI/netI     0.1752
_diffrn_reflns_av_R_equivalents  0.1237
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.661
_diffrn_reflns_theta_max         24.843
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.771
_diffrn_measured_fraction_theta_full 0.805
_diffrn_reflns_Laue_measured_fraction_max 0.771
_diffrn_reflns_Laue_measured_fraction_full 0.805
_diffrn_reflns_point_group_measured_fraction_max 0.671
_diffrn_reflns_point_group_measured_fraction_full 0.702
_reflns_number_total             9041
_reflns_number_gt                5455
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.656
_reflns_Friedel_fraction_max     0.560
_reflns_Friedel_fraction_full    0.588

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'GDA 8.44; generic data acquisition software'
_computing_cell_refinement       
'XIA2 0.4.0.438-g4431aaa, Winter, G. (2010) J. Appl. Cryst. 43'
_computing_data_reduction        
'XIA2 0.4.0.438-g4431aaa, Winter, G. (2010) J. Appl. Cryst. 43'
_computing_structure_solution    'SHELXT Acta Cryst. (2015). A71, 3-8'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0434P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1624 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         9041
_refine_ls_number_parameters     940
_refine_ls_number_restraints     397
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0721
_refine_ls_wR_factor_ref         0.1969
_refine_ls_wR_factor_gt          0.1755
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_restrained_S_all      0.908
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 1.6688(4) 1.6191(5) 1.05939(18) 0.0727(14) Uani 1 1 d . . . . .
O4 O 1.1553(4) 1.6200(5) 1.03263(19) 0.0794(15) Uani 1 1 d . . . . .
O2 O 1.5917(4) 1.3977(5) 1.4757(2) 0.0781(15) Uani 1 1 d . . . . .
N2 N 1.9223(5) 1.3710(5) 1.3833(2) 0.0652(15) Uani 1 1 d . . . . .
N1 N 1.7494(5) 1.3844(6) 1.4030(2) 0.0710(17) Uani 1 1 d . . . . .
H1 H 1.7127 1.3692 1.4294 0.085 Uiso 1 1 calc R U . A 1
N7 N 1.3767(5) 1.3884(6) 1.4494(2) 0.086(2) Uani 1 1 d . . . . .
H7A H 1.4354 1.4078 1.4368 0.103 Uiso 1 1 calc R U . . .
H7B H 1.3111 1.3952 1.4275 0.103 Uiso 1 1 calc R U . . .
N6 N 1.4838(5) 1.3353(5) 1.5383(2) 0.0649(16) Uani 1 1 d . . . . .
N9 N 1.3653(5) 1.6397(6) 1.1028(2) 0.0673(17) Uani 1 1 d . . . . .
H9B H 1.3048 1.6306 1.0770 0.081 Uiso 1 1 calc R U . . .
N10 N 1.5545(5) 1.6318(5) 1.1242(2) 0.0644(16) Uani 1 1 d . . . . .
N14 N 0.9953(5) 1.6857(6) 0.9741(2) 0.0696(17) Uani 1 1 d . . . . .
N13 N 0.8203(5) 1.6825(6) 0.9924(2) 0.0720(18) Uani 1 1 d . . . . .
H13B H 0.7789 1.6745 1.0174 0.086 Uiso 1 1 calc R U . . .
N5 N 1.2952(5) 1.3186(6) 1.5184(2) 0.0768(18) Uani 1 1 d . . . . .
H5B H 1.2344 1.3300 1.4932 0.092 Uiso 1 1 calc R U . . .
N15 N 0.9604(5) 1.6131(6) 1.0603(2) 0.0796(19) Uani 1 1 d . . . . .
H15B H 1.0301 1.5973 1.0734 0.096 Uiso 1 1 calc R U . . .
H15C H 0.9114 1.5984 1.0806 0.096 Uiso 1 1 calc R U . . .
N11 N 1.4533(5) 1.6165(7) 1.0304(2) 0.090(2) Uani 1 1 d . . . . .
H11A H 1.5134 1.6096 1.0169 0.108 Uiso 1 1 calc R U . . .
H11B H 1.3886 1.6153 1.0073 0.108 Uiso 1 1 calc R U . . .
N3 N 1.8913(5) 1.3734(7) 1.4764(2) 0.090(2) Uani 1 1 d . . . . .
H3A H 1.8442 1.3783 1.4988 0.108 Uiso 1 1 calc R U . . .
H3B H 1.9620 1.3672 1.4908 0.108 Uiso 1 1 calc R U . . .
N16 N 1.2665(5) 1.7288(7) 0.9567(2) 0.089(2) Uani 1 1 d . . . . .
C7 C 1.8558(6) 1.3751(6) 1.4215(2) 0.0601(18) Uani 1 1 d . . . . .
C60 C 0.7676(6) 1.7185(7) 0.9384(3) 0.067(2) Uani 1 1 d . . . . .
N8 N 1.7660(5) 1.2874(6) 1.5517(2) 0.0779(19) Uani 1 1 d . . . . .
C62 C 1.1026(6) 1.6583(8) 0.9880(3) 0.074(2) Uani 1 1 d . . . . .
N12 N 1.8433(5) 1.6076(7) 1.1545(2) 0.082(2) Uani 1 1 d . . . . .
C25 C 1.3874(6) 1.3483(7) 1.5023(3) 0.070(2) Uani 1 1 d . . . . .
C42 C 1.3508(6) 1.6640(7) 1.1574(3) 0.0618(19) Uani 1 1 d . . . . .
C47 C 1.6726(6) 1.8752(7) 1.1423(3) 0.071(2) Uani 1 1 d . . . . .
C41 C 1.4136(6) 1.7423(7) 1.1910(3) 0.070(2) Uani 1 1 d . . . . .
H41 H 1.4716 1.7786 1.1781 0.083 Uiso 1 1 calc R U . . .
C31 C 1.5013(7) 1.6682(8) 1.6193(3) 0.079(2) Uani 1 1 d . . . . .
H31 H 1.4485 1.7195 1.6001 0.094 Uiso 1 1 calc R U . . .
C52 C 1.5909(7) 1.8932(8) 1.0945(3) 0.074(2) Uani 1 1 d . . . . .
H52 H 1.5932 1.8542 1.0608 0.089 Uiso 1 1 calc R U . . .
C44 C 1.6513(6) 1.6362(7) 1.1073(3) 0.068(2) Uani 1 1 d . . . . .
C65 C 1.0663(8) 1.5010(8) 0.8894(3) 0.083(2) Uani 1 1 d . . . . .
C38 C 1.2476(6) 1.6356(8) 1.2286(3) 0.082(2) Uani 1 1 d . . . . .
H38 H 1.1913 1.5976 1.2421 0.098 Uiso 1 1 calc R U . . .
C43 C 1.4603(6) 1.6287(7) 1.0849(3) 0.0662(19) Uani 1 1 d . . . . .
C24 C 1.2799(6) 1.2719(7) 1.5695(3) 0.066(2) Uani 1 1 d . . . . .
C29 C 1.6450(7) 1.5358(8) 1.6171(3) 0.077(2) Uani 1 1 d . . . . .
C23 C 1.3513(6) 1.2868(8) 1.6212(3) 0.075(2) Uani 1 1 d . . . . .
H23 H 1.4173 1.3282 1.6238 0.090 Uiso 1 1 calc R U . . .
C45 C 1.7457(6) 1.6758(8) 1.1533(3) 0.070(2) Uani 1 1 d . . . . .
H45 H 1.7236 1.6695 1.1905 0.084 Uiso 1 1 calc R U . . .
C34 C 1.6525(7) 1.5183(8) 1.6742(3) 0.080(2) Uani 1 1 d . . . . .
H34 H 1.7029 1.4646 1.6933 0.096 Uiso 1 1 calc R U . . .
C30 C 1.5675(8) 1.6100(8) 1.5902(3) 0.080(2) Uani 1 1 d . . . . .
H30 H 1.5594 1.6216 1.5509 0.096 Uiso 1 1 calc R U . . .
C63 C 1.1597(6) 1.6757(8) 0.9385(3) 0.075(2) Uani 1 1 d . . . . .
H63 H 1.1123 1.7224 0.9090 0.090 Uiso 1 1 calc R U . . .
C55 C 0.6876(7) 1.8008(8) 0.9330(3) 0.083(2) Uani 1 1 d . . . . .
H55 H 0.6688 1.8315 0.9658 0.099 Uiso 1 1 calc R U . . .
C26 C 1.5781(6) 1.3627(7) 1.5226(3) 0.069(2) Uani 1 1 d . . . . .
C32 C 1.5122(7) 1.6511(7) 1.6767(3) 0.077(2) Uani 1 1 d . . . . .
H32 H 1.4670 1.6907 1.6971 0.092 Uiso 1 1 calc R U . . .
C61 C 0.9295(6) 1.6586(7) 1.0100(3) 0.072(2) Uani 1 1 d . . . . .
C48 C 1.6636(8) 1.9324(8) 1.1914(3) 0.085(3) Uani 1 1 d . . . . .
H48 H 1.7176 1.9204 1.2248 0.102 Uiso 1 1 calc R U . . .
C20 C 1.1608(7) 1.1611(7) 1.6149(3) 0.077(2) Uani 1 1 d . . . . .
H20 H 1.0959 1.1182 1.6125 0.092 Uiso 1 1 calc R U . . .
C56 C 0.6351(7) 1.8385(8) 0.8806(3) 0.088(3) Uani 1 1 d . . . . .
H56 H 0.5797 1.8938 0.8776 0.106 Uiso 1 1 calc R U . . .
C37 C 1.2652(6) 1.6111(7) 1.1764(3) 0.0662(19) Uani 1 1 d . . . . .
H37 H 1.2198 1.5586 1.1531 0.079 Uiso 1 1 calc R U . . .
C19 C 1.1847(7) 1.2072(8) 1.5676(3) 0.077(2) Uani 1 1 d . . . . .
H19 H 1.1358 1.1955 1.5324 0.093 Uiso 1 1 calc R U . . .
C70 C 1.0137(7) 1.5214(7) 0.8345(3) 0.073(2) Uani 1 1 d . . . . .
H70 H 1.0460 1.5720 0.8126 0.087 Uiso 1 1 calc R U . . .
C59 C 0.7948(6) 1.6760(7) 0.8903(3) 0.074(2) Uani 1 1 d . . . . .
H59 H 0.8504 1.6210 0.8928 0.089 Uiso 1 1 calc R U . . .
C49 C 1.5778(8) 2.0063(8) 1.1928(3) 0.086(2) Uani 1 1 d . . . . .
H49 H 1.5742 2.0443 1.2267 0.103 Uiso 1 1 calc R U . . .
C39 C 1.3102(7) 1.7149(10) 1.2623(3) 0.100(3) Uani 1 1 d . . . . .
H39 H 1.2960 1.7322 1.2983 0.119 Uiso 1 1 calc R U . . .
C35 C 1.8625(6) 1.2723(9) 1.5973(3) 0.088(3) Uani 1 1 d . . . . .
H35A H 1.8389 1.2487 1.6315 0.131 Uiso 1 1 calc R U . . .
H35B H 1.9026 1.3428 1.6043 0.131 Uiso 1 1 calc R U . . .
H35C H 1.9105 1.2153 1.5864 0.131 Uiso 1 1 calc R U . . .
C64 C 1.1723(7) 1.5580(9) 0.9148(3) 0.088(3) Uani 1 1 d . . . . .
H64A H 1.2172 1.5637 0.8857 0.106 Uiso 1 1 calc R U . . .
H64B H 1.2131 1.5108 0.9455 0.106 Uiso 1 1 calc R U . . .
C50 C 1.5000(8) 2.0237(8) 1.1459(3) 0.087(3) Uani 1 1 d . . . . .
H50 H 1.4412 2.0737 1.1467 0.105 Uiso 1 1 calc R U . . .
C66 C 1.0153(10) 1.4262(9) 0.9202(4) 0.096(3) Uani 1 1 d . . . . .
H66 H 1.0488 1.4110 0.9583 0.115 Uiso 1 1 calc R U . . .
C28 C 1.7195(7) 1.4710(9) 1.5862(4) 0.090(3) Uani 1 1 d . . . . .
H28A H 1.7261 1.5125 1.5519 0.108 Uiso 1 1 calc R U . . .
H28B H 1.7937 1.4660 1.6107 0.108 Uiso 1 1 calc R U . . .
C69 C 0.9168(8) 1.4714(8) 0.8105(4) 0.090(3) Uani 1 1 d . . . . .
H69 H 0.8817 1.4870 0.7727 0.108 Uiso 1 1 calc R U . . .
C57 C 0.6630(7) 1.7961(8) 0.8326(3) 0.082(2) Uani 1 1 d . . . . .
H57 H 0.6287 1.8236 0.7965 0.098 Uiso 1 1 calc R U . . .
C58 C 0.7393(7) 1.7151(8) 0.8375(3) 0.081(2) Uani 1 1 d . . . . .
H58 H 0.7560 1.6837 0.8044 0.098 Uiso 1 1 calc R U . . .
C27 C 1.6788(6) 1.3554(7) 1.5698(3) 0.071(2) Uani 1 1 d . . . . .
H27 H 1.6579 1.3188 1.6030 0.086 Uiso 1 1 calc R U . . .
C51 C 1.5060(8) 1.9677(8) 1.0957(3) 0.086(3) Uani 1 1 d . . . . .
H51 H 1.4518 1.9809 1.0625 0.103 Uiso 1 1 calc R U . . .
C33 C 1.5886(7) 1.5770(8) 1.7037(3) 0.080(2) Uani 1 1 d . . . . .
H33 H 1.5974 1.5660 1.7432 0.097 Uiso 1 1 calc R U . . .
C46 C 1.7665(7) 1.7991(8) 1.1418(3) 0.082(2) Uani 1 1 d . . . . .
H46A H 1.8301 1.8251 1.1705 0.098 Uiso 1 1 calc R U . . .
H46B H 1.7870 1.8048 1.1047 0.098 Uiso 1 1 calc R U . . .
C36 C 1.7222(7) 1.1775(8) 1.5320(3) 0.086(2) Uani 1 1 d . . . . .
H36A H 1.6966 1.1390 1.5624 0.129 Uiso 1 1 calc R U . . .
H36B H 1.7800 1.1334 1.5205 0.129 Uiso 1 1 calc R U . . .
H36C H 1.6606 1.1867 1.4998 0.129 Uiso 1 1 calc R U . . .
C53 C 1.8214(7) 1.4911(9) 1.1702(3) 0.090(3) Uani 1 1 d . . . . .
H53A H 1.7575 1.4620 1.1435 0.135 Uiso 1 1 calc R U . . .
H53B H 1.8067 1.4901 1.2083 0.135 Uiso 1 1 calc R U . . .
H53C H 1.8857 1.4447 1.1691 0.135 Uiso 1 1 calc R U . . .
C21 C 1.2308(7) 1.1771(8) 1.6657(3) 0.085(3) Uani 1 1 d . . . . .
H21 H 1.2147 1.1448 1.6988 0.102 Uiso 1 1 calc R U . . .
C68 C 0.8705(10) 1.3962(9) 0.8432(5) 0.114(3) Uani 1 1 d . . . . .
H68 H 0.8036 1.3597 0.8271 0.137 Uiso 1 1 calc R U . . .
C67 C 0.9198(11) 1.3752(9) 0.8971(6) 0.110(3) Uani 1 1 d . . . . .
H67 H 0.8874 1.3245 0.9188 0.132 Uiso 1 1 calc R U . . .
C40 C 1.3933(7) 1.7686(9) 1.2431(3) 0.089(3) Uani 1 1 d . . . . .
H40 H 1.4363 1.8236 1.2658 0.107 Uiso 1 1 calc R U . . .
C71 C 1.3256(7) 1.7404(10) 0.9098(3) 0.100(3) Uani 1 1 d . . . . .
H71A H 1.2757 1.7713 0.8767 0.149 Uiso 1 1 calc R U . . .
H71B H 1.3514 1.6671 0.9005 0.149 Uiso 1 1 calc R U . . .
H71C H 1.3885 1.7903 0.9213 0.149 Uiso 1 1 calc R U . . .
C72 C 1.2517(8) 1.8384(11) 0.9796(4) 0.111(4) Uani 1 1 d . . . . .
H72A H 1.2104 1.8314 1.0096 0.166 Uiso 1 1 calc R U . . .
H72B H 1.2111 1.8862 0.9496 0.166 Uiso 1 1 calc R U . . .
H72C H 1.3237 1.8716 0.9949 0.166 Uiso 1 1 calc R U . . .
C22 C 1.3244(7) 1.2399(9) 1.6690(3) 0.086(3) Uani 1 1 d . . . . .
H22 H 1.3716 1.2515 1.7047 0.103 Uiso 1 1 calc R U . . .
C54 C 1.9429(7) 1.6467(10) 1.1923(3) 0.099(3) Uani 1 1 d . . . . .
H54A H 1.9272 1.6619 1.2295 0.148 Uiso 1 1 calc R U . . .
H54B H 1.9685 1.7150 1.1772 0.148 Uiso 1 1 calc R U . . .
H54C H 2.0000 1.5894 1.1958 0.148 Uiso 1 1 calc R U . . .
C1A C 1.7031(11) 1.3680(14) 1.3043(5) 0.064(4) Uani 0.534(10) 1 d D U P B 1
H1A H 1.7628 1.3183 1.3051 0.077 Uiso 0.534(10) 1 calc R U P B 1
C2A C 1.6341(11) 1.3990(15) 1.2529(6) 0.074(4) Uani 0.534(10) 1 d D U P B 1
H2A H 1.6479 1.3701 1.2186 0.089 Uiso 0.534(10) 1 calc R U P B 1
C3A C 1.5475(14) 1.4704(15) 1.2516(7) 0.080(5) Uani 0.534(10) 1 d D U P B 1
H3A1 H 1.5036 1.4915 1.2163 0.096 Uiso 0.534(10) 1 calc R U P B 1
C4A C 1.5232(11) 1.5118(12) 1.3002(5) 0.075(4) Uani 0.534(10) 1 d D U P B 1
H4A H 1.4623 1.5602 1.2989 0.091 Uiso 0.534(10) 1 calc R U P B 1
C5A C 1.5900(9) 1.4813(12) 1.3514(5) 0.066(4) Uani 0.534(10) 1 d D U P B 1
H5A H 1.5734 1.5079 1.3855 0.079 Uiso 0.534(10) 1 calc R U P B 1
C6A C 1.6817(11) 1.4116(13) 1.3535(6) 0.059(4) Uani 0.534(10) 1 d D U P B 1
C1 C 1.7420(11) 1.2818(14) 1.3077(5) 0.058(4) Uani 0.466(10) 1 d D U P B 2
H1B H 1.8001 1.2335 1.3245 0.069 Uiso 0.466(10) 1 calc R U P B 2
C2 C 1.6932(11) 1.2723(13) 1.2506(5) 0.070(4) Uani 0.466(10) 1 d D U P B 2
H2 H 1.7204 1.2186 1.2282 0.084 Uiso 0.466(10) 1 calc R U P B 2
C3 C 1.6064(12) 1.3393(14) 1.2259(6) 0.072(5) Uani 0.466(10) 1 d D U P B 2
H3 H 1.5728 1.3308 1.1873 0.087 Uiso 0.466(10) 1 calc R U P B 2
C4 C 1.5694(17) 1.4182(18) 1.2581(6) 0.070(5) Uani 0.466(10) 1 d D U P B 2
H4 H 1.5105 1.4657 1.2415 0.084 Uiso 0.466(10) 1 calc R U P B 2
C5 C 1.6170(12) 1.4295(14) 1.3144(6) 0.066(4) Uani 0.466(10) 1 d D U P B 2
H5 H 1.5895 1.4838 1.3363 0.079 Uiso 0.466(10) 1 calc R U P B 2
C6 C 1.7040(13) 1.3628(14) 1.3393(7) 0.059(4) Uani 0.466(10) 1 d D U P B 2
O1A O 2.0900(8) 1.3922(11) 1.4519(4) 0.056(3) Uiso 0.484(10) 1 d . . P C 1
N4A N 2.1932(10) 1.4073(14) 1.3580(5) 0.050(4) Uiso 0.484(10) 1 d . . P C 1
C18A C 2.2549(13) 1.3761(17) 1.3124(6) 0.064(4) Uiso 0.484(10) 1 d . . P C 1
H18A H 2.3132 1.4307 1.3119 0.095 Uiso 0.484(10) 1 calc R U P C 1
H18B H 2.2039 1.3757 1.2758 0.095 Uiso 0.484(10) 1 calc R U P C 1
H18C H 2.2873 1.3020 1.3203 0.095 Uiso 0.484(10) 1 calc R U P C 1
C17A C 2.1553(14) 1.5172(16) 1.3471(7) 0.051(5) Uiso 0.484(10) 1 d . . P C 1
H17A H 2.1280 1.5456 1.3794 0.077 Uiso 0.484(10) 1 calc R U P C 1
H17B H 2.0958 1.5181 1.3135 0.077 Uiso 0.484(10) 1 calc R U P C 1
H17C H 2.2158 1.5642 1.3406 0.077 Uiso 0.484(10) 1 calc R U P C 1
C8A C 2.0338(17) 1.377(2) 1.4034(8) 0.066(7) Uiso 0.484(10) 1 d . . P C 1
C9A C 2.0973(16) 1.3323(16) 1.3575(7) 0.054(5) Uiso 0.484(10) 1 d . . P C 1
H9A H 2.0477 1.3319 1.3194 0.065 Uiso 0.484(10) 1 calc R U P C 1
C10A C 2.1391(16) 1.2133(16) 1.3744(8) 0.065(5) Uani 0.484(10) 1 d . . P C 1
H10A H 2.1844 1.2147 1.4131 0.078 Uiso 0.484(10) 1 calc R U P C 1
H10B H 2.1862 1.1879 1.3487 0.078 Uiso 0.484(10) 1 calc R U P C 1
C11A C 2.0372(17) 1.125(2) 1.3718(6) 0.078(4) Uani 0.484(10) 1 d D U P C 1
C12A C 2.0064(11) 1.0787(12) 1.3186(5) 0.068(4) Uani 0.484(10) 1 d D U P C 1
H12A H 2.0420 1.1001 1.2892 0.081 Uiso 0.484(10) 1 calc R U P C 1
C13A C 1.9234(12) 1.0014(14) 1.3091(6) 0.076(5) Uani 0.484(10) 1 d D U P C 1
H13A H 1.9014 0.9663 1.2735 0.092 Uiso 0.484(10) 1 calc R U P C 1
C14A C 1.8729(12) 0.9765(14) 1.3532(5) 0.072(5) Uani 0.484(10) 1 d D U P C 1
H14A H 1.8143 0.9243 1.3469 0.087 Uiso 0.484(10) 1 calc R U P C 1
C15A C 1.9032(15) 1.0231(18) 1.4049(7) 0.083(7) Uani 0.484(10) 1 d D U P C 1
H15A H 1.8605 1.0116 1.4325 0.100 Uiso 0.484(10) 1 calc R U P C 1
C16A C 1.995(2) 1.086(4) 1.4165(6) 0.078(3) Uani 0.484(10) 1 d D U P C 1
H16A H 2.0290 1.1028 1.4542 0.093 Uiso 0.484(10) 1 calc R U P C 1
O1 O 2.0836(7) 1.3387(10) 1.4463(4) 0.055(3) Uiso 0.516(10) 1 d . . P C 2
N4 N 2.1723(11) 1.3635(12) 1.3479(5) 0.055(3) Uiso 0.516(10) 1 d . . P C 2
C18 C 2.2293(13) 1.3263(16) 1.3029(6) 0.066(4) Uiso 0.516(10) 1 d . . P C 2
H18D H 2.3034 1.3582 1.3097 0.098 Uiso 0.516(10) 1 calc R U P C 2
H18E H 2.1877 1.3513 1.2662 0.098 Uiso 0.516(10) 1 calc R U P C 2
H18F H 2.2343 1.2449 1.3032 0.098 Uiso 0.516(10) 1 calc R U P C 2
C17 C 2.1501(17) 1.476(2) 1.3428(8) 0.073(6) Uiso 0.516(10) 1 d . . P C 2
H17D H 2.1001 1.4905 1.3067 0.109 Uiso 0.516(10) 1 calc R U P C 2
H17E H 2.2187 1.5171 1.3446 0.109 Uiso 0.516(10) 1 calc R U P C 2
H17F H 2.1157 1.5001 1.3736 0.109 Uiso 0.516(10) 1 calc R U P C 2
C8 C 2.0270(13) 1.3400(16) 1.3974(6) 0.049(5) Uiso 0.516(10) 1 d . . P C 2
C9 C 2.0710(16) 1.3004(18) 1.3479(8) 0.072(6) Uiso 0.516(10) 1 d . . P C 2
H9 H 2.0162 1.3177 1.3126 0.086 Uiso 0.516(10) 1 calc R U P C 2
C10 C 2.0861(17) 1.1757(18) 1.3527(7) 0.073(6) Uani 0.516(10) 1 d . . P C 2
H10D H 2.1051 1.1473 1.3176 0.088 Uiso 0.516(10) 1 calc R U P C 2
H10E H 2.1485 1.1590 1.3842 0.088 Uiso 0.516(10) 1 calc R U P C 2
C11 C 1.9921(15) 1.1198(18) 1.3618(5) 0.078(4) Uani 0.516(10) 1 d D U P C 2
C12 C 1.8939(11) 1.1084(12) 1.3249(6) 0.079(4) Uani 0.516(10) 1 d D U P C 2
H12 H 1.8893 1.1324 1.2872 0.095 Uiso 0.516(10) 1 calc R U P C 2
C13 C 1.7995(13) 1.0636(13) 1.3391(6) 0.084(4) Uani 0.516(10) 1 d D U P C 2
H13 H 1.7336 1.0585 1.3112 0.101 Uiso 0.516(10) 1 calc R U P C 2
C14 C 1.8009(13) 1.0267(13) 1.3931(5) 0.081(5) Uani 0.516(10) 1 d D U P C 2
H14 H 1.7376 0.9961 1.4035 0.097 Uiso 0.516(10) 1 calc R U P C 2
C15 C 1.9015(12) 1.0371(16) 1.4316(7) 0.082(6) Uani 0.516(10) 1 d D U P C 2
H15 H 1.9100 1.0060 1.4682 0.098 Uiso 0.516(10) 1 calc R U P C 2
C16 C 1.990(2) 1.094(3) 1.4162(5) 0.078(3) Uani 0.516(10) 1 d D U P C 2
H16 H 2.0510 1.1143 1.4449 0.093 Uiso 0.516(10) 1 calc R U P C 2


_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
O3 C44 1.245(7) . ?
O4 C62 1.233(8) . ?
O2 C26 1.257(8) . ?
N2 C8 1.330(17) . ?
N2 C7 1.367(8) . ?
N2 C8A 1.37(2) . ?
N1 C7 1.312(8) . ?
N1 C6A 1.357(14) . ?
N1 C6 1.553(17) . ?
N1 H1 0.8800 . ?
N7 C25 1.352(9) . ?
N7 H7A 0.8800 . ?
N7 H7B 0.8800 . ?
N6 C25 1.339(9) . ?
N6 C26 1.348(9) . ?
N9 C43 1.349(9) . ?
N9 C42 1.406(8) . ?
N9 H9B 0.8800 . ?
N10 C43 1.349(9) . ?
N10 C44 1.352(9) . ?
N14 C62 1.349(10) . ?
N14 C61 1.354(9) . ?
N13 C61 1.367(9) . ?
N13 C60 1.407(9) . ?
N13 H13B 0.8800 . ?
N5 C25 1.336(9) . ?
N5 C24 1.409(9) . ?
N5 H5B 0.8800 . ?
N15 C61 1.319(9) . ?
N15 H15B 0.8800 . ?
N15 H15C 0.8800 . ?
N11 C43 1.316(8) . ?
N11 H11A 0.8800 . ?
N11 H11B 0.8800 . ?
N3 C7 1.313(8) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N16 C72 1.455(14) . ?
N16 C63 1.458(10) . ?
N16 C71 1.485(10) . ?
C60 C59 1.382(10) . ?
C60 C55 1.389(12) . ?
N8 C35 1.464(9) . ?
N8 C36 1.470(12) . ?
N8 C27 1.496(10) . ?
C62 C63 1.533(11) . ?
N12 C54 1.458(10) . ?
N12 C45 1.461(10) . ?
N12 C53 1.490(12) . ?
C42 C41 1.377(11) . ?
C42 C37 1.399(10) . ?
C47 C52 1.390(10) . ?
C47 C48 1.402(11) . ?
C47 C46 1.485(12) . ?
C41 C40 1.378(9) . ?
C41 H41 0.9500 . ?
C31 C30 1.381(11) . ?
C31 C32 1.387(10) . ?
C31 H31 0.9500 . ?
C52 C51 1.390(12) . ?
C52 H52 0.9500 . ?
C44 C45 1.518(10) . ?
C65 C70 1.380(10) . ?
C65 C66 1.403(13) . ?
C65 C64 1.499(13) . ?
C38 C37 1.362(10) . ?
C38 C39 1.385(13) . ?
C38 H38 0.9500 . ?
C24 C23 1.390(9) . ?
C24 C19 1.410(11) . ?
C29 C30 1.374(12) . ?
C29 C34 1.387(10) . ?
C29 C28 1.522(12) . ?
C23 C22 1.394(11) . ?
C23 H23 0.9500 . ?
C45 C46 1.540(12) . ?
C45 H45 1.0000 . ?
C34 C33 1.372(11) . ?
C34 H34 0.9500 . ?
C30 H30 0.9500 . ?
C63 C64 1.547(12) . ?
C63 H63 1.0000 . ?
C55 C56 1.380(11) . ?
C55 H55 0.9500 . ?
C26 C27 1.515(10) . ?
C32 C33 1.366(11) . ?
C32 H32 0.9500 . ?
C48 C49 1.395(13) . ?
C48 H48 0.9500 . ?
C20 C21 1.368(11) . ?
C20 C19 1.361(11) . ?
C20 H20 0.9500 . ?
C56 C57 1.383(11) . ?
C56 H56 0.9500 . ?
C37 H37 0.9500 . ?
C19 H19 0.9500 . ?
C70 C69 1.364(12) . ?
C70 H70 0.9500 . ?
C59 C58 1.403(10) . ?
C59 H59 0.9500 . ?
C49 C50 1.349(12) . ?
C49 H49 0.9500 . ?
C39 C40 1.379(12) . ?
C39 H39 0.9500 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C64 H64A 0.9900 . ?
C64 H64B 0.9900 . ?
C50 C51 1.407(11) . ?
C50 H50 0.9500 . ?
C66 C67 1.351(14) . ?
C66 H66 0.9500 . ?
C28 C27 1.503(12) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C69 C68 1.403(14) . ?
C69 H69 0.9500 . ?
C57 C58 1.347(11) . ?
C57 H57 0.9500 . ?
C58 H58 0.9500 . ?
C27 H27 1.0000 . ?
C51 H51 0.9500 . ?
C33 H33 0.9500 . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C21 C22 1.376(12) . ?
C21 H21 0.9500 . ?
C68 C67 1.348(15) . ?
C68 H68 0.9500 . ?
C67 H67 0.9500 . ?
C40 H40 0.9500 . ?
C71 H71A 0.9800 . ?
C71 H71B 0.9800 . ?
C71 H71C 0.9800 . ?
C72 H72A 0.9800 . ?
C72 H72B 0.9800 . ?
C72 H72C 0.9800 . ?
C22 H22 0.9500 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C1A C6A 1.379(15) . ?
C1A C2A 1.410(15) . ?
C1A H1A 0.9500 . ?
C2A C3A 1.372(16) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.372(15) . ?
C3A H3A1 0.9500 . ?
C4A C5A 1.394(14) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.408(15) . ?
C5A H5A 0.9500 . ?
C1 C6 1.383(16) . ?
C1 C2 1.399(14) . ?
C1 H1B 0.9500 . ?
C2 C3 1.380(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.367(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(16) . ?
C5 H5 0.9500 . ?
O1A C8A 1.25(2) . ?
N4A C17A 1.41(3) . ?
N4A C9A 1.49(3) . ?
N4A C18A 1.52(2) . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
C8A C9A 1.59(3) . ?
C9A C10A 1.55(2) . ?
C9A H9A 1.0000 . ?
C10A C11A 1.65(3) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A C12A 1.383(17) . ?
C11A C16A 1.385(16) . ?
C12A C13A 1.372(16) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.381(15) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.354(16) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.344(17) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
O1 C8 1.247(17) . ?
N4 C17 1.38(3) . ?
N4 C9 1.47(3) . ?
N4 C18 1.490(19) . ?
C18 H18D 0.9800 . ?
C18 H18E 0.9800 . ?
C18 H18F 0.9800 . ?
C17 H17D 0.9800 . ?
C17 H17E 0.9800 . ?
C17 H17F 0.9800 . ?
C8 C9 1.50(2) . ?
C9 C10 1.51(3) . ?
C9 H9 1.0000 . ?
C10 C11 1.41(3) . ?
C10 H10D 0.9900 . ?
C10 H10E 0.9900 . ?
C11 C16 1.362(16) . ?
C11 C12 1.363(16) . ?
C12 C13 1.400(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(15) . ?
C13 H13 0.9500 . ?
C14 C15 1.404(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.411(16) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

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
C8 N2 C7 122.3(8) . . ?
C7 N2 C8A 117.8(9) . . ?
C7 N1 C6A 136.1(8) . . ?
C7 N1 C6 117.3(8) . . ?
C7 N1 H1 111.9 . . ?
C6A N1 H1 111.9 . . ?
C25 N7 H7A 120.0 . . ?
C25 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C25 N6 C26 120.1(6) . . ?
C43 N9 C42 128.2(6) . . ?
C43 N9 H9B 115.9 . . ?
C42 N9 H9B 115.9 . . ?
C43 N10 C44 119.0(5) . . ?
C62 N14 C61 118.8(6) . . ?
C61 N13 C60 126.6(6) . . ?
C61 N13 H13B 116.7 . . ?
C60 N13 H13B 116.7 . . ?
C25 N5 C24 130.3(6) . . ?
C25 N5 H5B 114.9 . . ?
C24 N5 H5B 114.9 . . ?
C61 N15 H15B 120.0 . . ?
C61 N15 H15C 120.0 . . ?
H15B N15 H15C 120.0 . . ?
C43 N11 H11A 120.0 . . ?
C43 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
C7 N3 H3A 120.0 . . ?
C7 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C72 N16 C63 109.4(7) . . ?
C72 N16 C71 109.3(8) . . ?
C63 N16 C71 112.0(6) . . ?
N3 C7 N1 116.8(6) . . ?
N3 C7 N2 124.5(6) . . ?
N1 C7 N2 118.7(5) . . ?
C59 C60 C55 118.7(7) . . ?
C59 C60 N13 121.8(7) . . ?
C55 C60 N13 119.5(6) . . ?
C35 N8 C36 109.0(7) . . ?
C35 N8 C27 112.1(6) . . ?
C36 N8 C27 110.1(6) . . ?
O4 C62 N14 128.8(7) . . ?
O4 C62 C63 119.5(7) . . ?
N14 C62 C63 111.7(6) . . ?
C54 N12 C45 115.2(7) . . ?
C54 N12 C53 108.6(7) . . ?
C45 N12 C53 109.6(6) . . ?
N6 C25 N5 119.0(6) . . ?
N6 C25 N7 124.0(7) . . ?
N5 C25 N7 117.0(7) . . ?
C41 C42 N9 122.2(6) . . ?
C41 C42 C37 119.5(6) . . ?
N9 C42 C37 118.2(7) . . ?
C52 C47 C48 117.3(9) . . ?
C52 C47 C46 122.0(7) . . ?
C48 C47 C46 120.7(8) . . ?
C42 C41 C40 120.7(7) . . ?
C42 C41 H41 119.6 . . ?
C40 C41 H41 119.6 . . ?
C30 C31 C32 119.7(8) . . ?
C30 C31 H31 120.2 . . ?
C32 C31 H31 120.2 . . ?
C47 C52 C51 120.7(7) . . ?
C47 C52 H52 119.6 . . ?
C51 C52 H52 119.6 . . ?
O3 C44 N10 128.1(7) . . ?
O3 C44 C45 118.6(6) . . ?
N10 C44 C45 113.0(6) . . ?
C70 C65 C66 116.9(9) . . ?
C70 C65 C64 121.0(8) . . ?
C66 C65 C64 122.0(8) . . ?
C37 C38 C39 121.2(7) . . ?
C37 C38 H38 119.4 . . ?
C39 C38 H38 119.4 . . ?
N11 C43 N10 125.4(6) . . ?
N11 C43 N9 117.2(7) . . ?
N10 C43 N9 117.4(5) . . ?
C23 C24 N5 124.4(7) . . ?
C23 C24 C19 118.4(7) . . ?
N5 C24 C19 117.2(6) . . ?
C30 C29 C34 117.9(7) . . ?
C30 C29 C28 122.5(7) . . ?
C34 C29 C28 119.6(9) . . ?
C24 C23 C22 118.7(8) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
N12 C45 C44 110.6(6) . . ?
N12 C45 C46 111.9(7) . . ?
C44 C45 C46 107.5(6) . . ?
N12 C45 H45 108.9 . . ?
C44 C45 H45 108.9 . . ?
C46 C45 H45 108.9 . . ?
C33 C34 C29 121.2(8) . . ?
C33 C34 H34 119.4 . . ?
C29 C34 H34 119.4 . . ?
C29 C30 C31 121.3(7) . . ?
C29 C30 H30 119.3 . . ?
C31 C30 H30 119.3 . . ?
N16 C63 C62 111.4(6) . . ?
N16 C63 C64 110.9(7) . . ?
C62 C63 C64 105.5(7) . . ?
N16 C63 H63 109.7 . . ?
C62 C63 H63 109.7 . . ?
C64 C63 H63 109.7 . . ?
C56 C55 C60 120.8(7) . . ?
C56 C55 H55 119.6 . . ?
C60 C55 H55 119.6 . . ?
O2 C26 N6 128.9(7) . . ?
O2 C26 C27 117.2(6) . . ?
N6 C26 C27 113.8(6) . . ?
C33 C32 C31 119.4(8) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
N15 C61 N14 126.6(7) . . ?
N15 C61 N13 117.1(7) . . ?
N14 C61 N13 116.3(6) . . ?
C49 C48 C47 122.0(8) . . ?
C49 C48 H48 119.0 . . ?
C47 C48 H48 119.0 . . ?
C21 C20 C19 119.6(8) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C55 C56 C57 120.3(8) . . ?
C55 C56 H56 119.9 . . ?
C57 C56 H56 119.9 . . ?
C38 C37 C42 119.4(7) . . ?
C38 C37 H37 120.3 . . ?
C42 C37 H37 120.3 . . ?
C20 C19 C24 121.8(7) . . ?
C20 C19 H19 119.1 . . ?
C24 C19 H19 119.1 . . ?
C69 C70 C65 122.2(8) . . ?
C69 C70 H70 118.9 . . ?
C65 C70 H70 118.9 . . ?
C60 C59 C58 119.2(7) . . ?
C60 C59 H59 120.4 . . ?
C58 C59 H59 120.4 . . ?
C50 C49 C48 119.8(8) . . ?
C50 C49 H49 120.1 . . ?
C48 C49 H49 120.1 . . ?
C40 C39 C38 119.4(7) . . ?
C40 C39 H39 120.3 . . ?
C38 C39 H39 120.3 . . ?
N8 C35 H35A 109.5 . . ?
N8 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
N8 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C65 C64 C63 114.9(6) . . ?
C65 C64 H64A 108.5 . . ?
C63 C64 H64A 108.5 . . ?
C65 C64 H64B 108.5 . . ?
C63 C64 H64B 108.5 . . ?
H64A C64 H64B 107.5 . . ?
C49 C50 C51 119.9(9) . . ?
C49 C50 H50 120.0 . . ?
C51 C50 H50 120.0 . . ?
C67 C66 C65 121.7(9) . . ?
C67 C66 H66 119.2 . . ?
C65 C66 H66 119.2 . . ?
C27 C28 C29 113.4(6) . . ?
C27 C28 H28A 108.9 . . ?
C29 C28 H28A 108.9 . . ?
C27 C28 H28B 108.9 . . ?
C29 C28 H28B 108.9 . . ?
H28A C28 H28B 107.7 . . ?
C70 C69 C68 118.3(9) . . ?
C70 C69 H69 120.8 . . ?
C68 C69 H69 120.8 . . ?
C58 C57 C56 119.1(8) . . ?
C58 C57 H57 120.4 . . ?
C56 C57 H57 120.4 . . ?
C57 C58 C59 121.8(7) . . ?
C57 C58 H58 119.1 . . ?
C59 C58 H58 119.1 . . ?
N8 C27 C28 111.0(6) . . ?
N8 C27 C26 110.2(5) . . ?
C28 C27 C26 109.1(7) . . ?
N8 C27 H27 108.8 . . ?
C28 C27 H27 108.8 . . ?
C26 C27 H27 108.8 . . ?
C52 C51 C50 120.2(9) . . ?
C52 C51 H51 119.9 . . ?
C50 C51 H51 119.9 . . ?
C34 C33 C32 120.4(7) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C47 C46 C45 115.4(7) . . ?
C47 C46 H46A 108.4 . . ?
C45 C46 H46A 108.4 . . ?
C47 C46 H46B 108.4 . . ?
C45 C46 H46B 108.4 . . ?
H46A C46 H46B 107.5 . . ?
N8 C36 H36A 109.5 . . ?
N8 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N8 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N12 C53 H53A 109.5 . . ?
N12 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
N12 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C20 C21 C22 120.1(7) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C67 C68 C69 120.7(11) . . ?
C67 C68 H68 119.6 . . ?
C69 C68 H68 119.6 . . ?
C66 C67 C68 120.2(10) . . ?
C66 C67 H67 119.9 . . ?
C68 C67 H67 119.9 . . ?
C39 C40 C41 119.8(8) . . ?
C39 C40 H40 120.1 . . ?
C41 C40 H40 120.1 . . ?
N16 C71 H71A 109.5 . . ?
N16 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
N16 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
N16 C72 H72A 109.5 . . ?
N16 C72 H72B 109.5 . . ?
H72A C72 H72B 109.5 . . ?
N16 C72 H72C 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 109.5 . . ?
C21 C22 C23 121.4(7) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
N12 C54 H54A 109.5 . . ?
N12 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
N12 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C6A C1A C2A 118.3(13) . . ?
C6A C1A H1A 120.8 . . ?
C2A C1A H1A 120.8 . . ?
C3A C2A C1A 121.0(14) . . ?
C3A C2A H2A 119.5 . . ?
C1A C2A H2A 119.5 . . ?
C4A C3A C2A 121.4(15) . . ?
C4A C3A H3A1 119.3 . . ?
C2A C3A H3A1 119.3 . . ?
C3A C4A C5A 118.3(13) . . ?
C3A C4A H4A 120.8 . . ?
C5A C4A H4A 120.8 . . ?
C4A C5A C6A 121.1(12) . . ?
C4A C5A H5A 119.5 . . ?
C6A C5A H5A 119.5 . . ?
N1 C6A C1A 118.6(11) . . ?
N1 C6A C5A 121.6(11) . . ?
C1A C6A C5A 119.8(12) . . ?
C6 C1 C2 118.7(14) . . ?
C6 C1 H1B 120.6 . . ?
C2 C1 H1B 120.6 . . ?
C3 C2 C1 121.4(14) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C4 C3 C2 118.9(15) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 120.6(16) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 120.9(14) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 119.5(14) . . ?
C5 C6 N1 115.4(12) . . ?
C1 C6 N1 125.1(11) . . ?
C17A N4A C9A 109.2(13) . . ?
C17A N4A C18A 107.1(13) . . ?
C9A N4A C18A 111.7(15) . . ?
N4A C18A H18A 109.5 . . ?
N4A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
N4A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
N4A C17A H17A 109.5 . . ?
N4A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
N4A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
O1A C8A N2 131.8(17) . . ?
O1A C8A C9A 116.6(17) . . ?
N2 C8A C9A 110.4(16) . . ?
N4A C9A C10A 109.4(15) . . ?
N4A C9A C8A 107.9(15) . . ?
C10A C9A C8A 108.2(15) . . ?
N4A C9A H9A 110.4 . . ?
C10A C9A H9A 110.4 . . ?
C8A C9A H9A 110.4 . . ?
C9A C10A C11A 111.9(16) . . ?
C9A C10A H10A 109.2 . . ?
C11A C10A H10A 109.2 . . ?
C9A C10A H10B 109.2 . . ?
C11A C10A H10B 109.2 . . ?
H10A C10A H10B 107.9 . . ?
C12A C11A C16A 121(2) . . ?
C12A C11A C10A 110.9(13) . . ?
C16A C11A C10A 127.3(15) . . ?
C13A C12A C11A 118.6(14) . . ?
C13A C12A H12A 120.7 . . ?
C11A C12A H12A 120.7 . . ?
C12A C13A C14A 117.7(13) . . ?
C12A C13A H13A 121.1 . . ?
C14A C13A H13A 121.1 . . ?
C15A C14A C13A 123.0(14) . . ?
C15A C14A H14A 118.5 . . ?
C13A C14A H14A 118.5 . . ?
C16A C15A C14A 119.0(18) . . ?
C16A C15A H15A 120.5 . . ?
C14A C15A H15A 120.5 . . ?
C15A C16A C11A 118.1(17) . . ?
C15A C16A H16A 121.0 . . ?
C11A C16A H16A 121.0 . . ?
C17 N4 C9 110.4(15) . . ?
C17 N4 C18 110.2(14) . . ?
C9 N4 C18 112.6(14) . . ?
N4 C18 H18D 109.5 . . ?
N4 C18 H18E 109.5 . . ?
H18D C18 H18E 109.5 . . ?
N4 C18 H18F 109.5 . . ?
H18D C18 H18F 109.5 . . ?
H18E C18 H18F 109.5 . . ?
N4 C17 H17D 109.5 . . ?
N4 C17 H17E 109.5 . . ?
H17D C17 H17E 109.5 . . ?
N4 C17 H17F 109.5 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?
O1 C8 N2 125.2(13) . . ?
O1 C8 C9 122.0(15) . . ?
N2 C8 C9 112.7(13) . . ?
N4 C9 C8 107.1(16) . . ?
N4 C9 C10 114.7(16) . . ?
C8 C9 C10 108.3(15) . . ?
N4 C9 H9 108.9 . . ?
C8 C9 H9 108.9 . . ?
C10 C9 H9 108.9 . . ?
C11 C10 C9 113.0(17) . . ?
C11 C10 H10D 109.0 . . ?
C9 C10 H10D 109.0 . . ?
C11 C10 H10E 109.0 . . ?
C9 C10 H10E 109.0 . . ?
H10D C10 H10E 107.8 . . ?
C16 C11 C12 114.8(17) . . ?
C16 C11 C10 116.5(14) . . ?
C12 C11 C10 127.3(13) . . ?
C11 C12 C13 124.1(13) . . ?
C11 C12 H12 118.0 . . ?
C13 C12 H12 118.0 . . ?
C14 C13 C12 120.9(14) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 115.9(14) . . ?
C13 C14 H14 122.1 . . ?
C15 C14 H14 122.1 . . ?
C14 C15 C16 120.3(17) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 122.8(16) . . ?
C11 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?

_refine_diff_density_max         0.819
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.056

