# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_mtf467_hklf5
_database_code_depnum_ccdc_archive 'CCDC 1982711'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;Spectropole RX   Universite Aix Marseille
France
;
_audit_update_record             
;
2020-02-07 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_audit_creation_date             2018-06-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H7 N3 O2'
_chemical_formula_sum            'C9 H7 N3 O2'
_chemical_formula_weight         189.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c9 h7 n3 o2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.5711(7)
_cell_length_b                   10.4626(6)
_cell_length_c                   7.7586(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.776(7)
_cell_angle_gamma                90
_cell_volume                     817.14(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3789
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.9620
_cell_measurement_theta_min      6.1190
_shelx_estimated_absorpt_T_max   0.928
_shelx_estimated_absorpt_T_min   0.833
_exptl_absorpt_coefficient_mu    0.950
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0070
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2839
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.828
_diffrn_reflns_theta_min         4.392
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00 -41.00   1.00    5.00    --  -41.07 -77.00 -60.00   27
  2  ω    -56.00 -18.00   1.00    5.00    --  -41.07 -38.00 -30.00   38
  3  ω   -117.00 -10.00   1.00    5.00    --  -41.07 -77.00 -30.00  107
  4  ω   -112.00 -61.00   1.00    5.00    --  -41.07 -57.00-150.00   51
  5  ω    -50.00 -25.00   1.00    5.00    --  -41.07 -57.00 -90.00   25
  6  ω   -117.00 -86.00   1.00    5.00    --  -41.07 -77.00 -60.00   31
  7  ω    -42.00 -16.00   1.00    5.00    --  -41.07 -57.00-150.00   26
  8  ω      5.00  71.00   1.00    5.00    --   41.07 -99.00-180.00   66
  9  ω      3.00  60.00   1.00    5.00    --   41.07 -99.00  60.00   57
 10  ω    110.00 177.00   1.00   20.00    --  101.41  77.00 -90.00   67
 11  ω    109.00 168.00   1.00   20.00    --  101.41  30.00  90.00   59
 12  ω     77.00 169.00   1.00   20.00    --  101.41  45.00 -30.00   92
 13  ω     73.00  98.00   1.00   20.00    --  101.41  61.00   0.00   25
 14  ω     98.00 123.00   1.00   20.00    --  101.41 125.00  90.00   25
 15  ω     69.00  95.00   1.00   20.00    --  101.41  77.00 -60.00   26
 16  ω     70.00  95.00   1.00   20.00    --  101.41  77.00 -90.00   25
 17  ω     30.00 129.00   1.00   20.00    --  101.41 -61.00 150.00   99
 18  ω     69.00 157.00   1.00   20.00    --  101.41  77.00  30.00   88
 19  ω     68.00  95.00   1.00   20.00    --  101.41 -94.00-120.00   27
 20  ω     69.00  95.00   1.00   20.00    --  101.41  77.00   0.00   26
 21  ω     73.00  98.00   1.00   20.00    --  101.41  61.00 -30.00   25
 22  ω     72.00  98.00   1.00   20.00    --  101.41  61.00 -90.00   26
 23  ω     70.00  95.00   1.00   20.00    --  101.41  77.00 -30.00   25
 24  ω     81.00 171.00   1.00   20.00    --  101.41  45.00   0.00   90
 25  ω     77.00 102.00   1.00   20.00    --  101.41  45.00  30.00   25
 26  ω     77.00 102.00   1.00   20.00    --  101.41  45.00 -60.00   25
 27  ω     73.00  98.00   1.00   20.00    --  101.41  61.00 -60.00   25
 28  ω    149.00 175.00   1.00   20.00    --  101.41 125.00  90.00   26
 29  ω     72.00  99.00   1.00   20.00    --  101.41  61.00  30.00   27
 30  ω     28.00 120.00   1.00   20.00    --  101.41 -45.00-120.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1148208000
_diffrn_orient_matrix_UB_12      -0.0499223000
_diffrn_orient_matrix_UB_13      -0.1605579000
_diffrn_orient_matrix_UB_21      0.0867600000
_diffrn_orient_matrix_UB_22      0.0162018000
_diffrn_orient_matrix_UB_23      -0.1260703000
_diffrn_orient_matrix_UB_31      0.0517730000
_diffrn_orient_matrix_UB_32      -0.1375471000
_diffrn_orient_matrix_UB_33      0.0432465000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2470
_reflns_number_total             2839
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2839
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0650P)²+0.1282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1181
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5650(17)
 0.4350(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
3.a Riding coordinates:
 N3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C6(H6), C7(H7)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.30663(12) 0.46789(11) 0.47215(19) 0.0542(4) Uani 1 1 d . . . . .
O2 O 0.30648(13) 0.98723(12) 0.4871(2) 0.0649(4) Uani 1 1 d . . . . .
N1 N 0.42859(13) 0.61564(13) 0.6539(2) 0.0434(4) Uani 1 1 d . . . . .
H1 H 0.487142 0.556063 0.686009 0.052 Uiso 1 1 calc R . . . .
N2 N 0.42293(13) 0.84670(13) 0.6892(2) 0.0433(4) Uani 1 1 d . . . . .
N3 N 0.57762(15) 0.72265(13) 0.8800(2) 0.0507(4) Uani 1 1 d . . . . .
H3A H 0.611985 0.793849 0.927160 0.061 Uiso 1 1 d R . . . .
H3B H 0.608925 0.649689 0.923940 0.061 Uiso 1 1 d R . . . .
C1 C 0.47018(15) 0.73178(14) 0.7385(3) 0.0388(4) Uani 1 1 d . . . . .
C2 C 0.31259(16) 0.57714(15) 0.5291(2) 0.0402(4) Uani 1 1 d . . . . .
C3 C 0.19436(15) 0.66228(15) 0.4716(2) 0.0384(4) Uani 1 1 d . . . . .
C4 C 0.07409(17) 0.59910(17) 0.3946(3) 0.0482(4) Uani 1 1 d . . . . .
H4 H 0.074104 0.510771 0.381126 0.058 Uiso 1 1 calc R . . . .
C5 C -0.04476(17) 0.66430(18) 0.3379(3) 0.0540(5) Uani 1 1 d . . . . .
H5 H -0.123966 0.619997 0.289550 0.065 Uiso 1 1 calc R . . . .
C6 C -0.04559(18) 0.7952(2) 0.3534(3) 0.0551(5) Uani 1 1 d . . . . .
H6 H -0.125423 0.839857 0.317393 0.066 Uiso 1 1 calc R . . . .
C7 C 0.07290(17) 0.85968(17) 0.4227(3) 0.0494(5) Uani 1 1 d . . . . .
H7 H 0.072009 0.948443 0.428588 0.059 Uiso 1 1 calc R . . . .
C8 C 0.19407(15) 0.79543(16) 0.4841(2) 0.0396(4) Uani 1 1 d . . . . .
C9 C 0.31405(16) 0.87916(15) 0.5516(3) 0.0428(4) Uani 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 C2 1.220(2) . ?
O2 C9 1.229(2) . ?
N1 H1 0.8600 . ?
N1 C1 1.387(2) . ?
N1 C2 1.370(2) . ?
N2 C1 1.313(2) . ?
N2 C9 1.353(2) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N3 C1 1.320(2) . ?
C2 C3 1.488(2) . ?
C3 C4 1.395(2) . ?
C3 C8 1.397(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.375(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.395(2) . ?
C8 C9 1.498(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1 113.7 . . ?
C2 N1 H1 113.7 . . ?
C2 N1 C1 132.66(14) . . ?
C1 N2 C9 128.04(14) . . ?
H3A N3 H3B 122.6 . . ?
C1 N3 H3A 115.8 . . ?
C1 N3 H3B 121.5 . . ?
N2 C1 N1 128.79(16) . . ?
N2 C1 N3 117.56(14) . . ?
N3 C1 N1 113.45(14) . . ?
O1 C2 N1 117.86(14) . . ?
O1 C2 C3 120.41(15) . . ?
N1 C2 C3 121.64(14) . . ?
C4 C3 C2 114.65(14) . . ?
C4 C3 C8 118.77(14) . . ?
C8 C3 C2 126.57(14) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.66(16) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.64(16) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 120.3 . . ?
C5 C6 C7 119.49(16) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 119.1 . . ?
C6 C7 C8 121.81(17) . . ?
C8 C7 H7 119.1 . . ?
C3 C8 C9 126.01(14) . . ?
C7 C8 C3 118.56(15) . . ?
C7 C8 C9 115.38(15) . . ?
O2 C9 N2 119.10(14) . . ?
O2 C9 C8 116.91(15) . . ?
N2 C9 C8 123.69(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.316
_oxdiff_exptl_absorpt_empirical_full_min 0.798
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_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 0.5650(17) 4053 2606 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.4350(17) 4052 2606 nmt 1.0000 0.0010 0.8315 0.0009 -0.9999 0.0006 0.0010
-0.0001 -0.9996

_twin_special_details            
;
Component 2 rotated by -179.9916° 
 around [1.00 0.00 0.00] (reciprocal) or [0.92 0.00 0.38] (direct)
;
####################################################################### 
# 
# 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_mtf478
_database_code_depnum_ccdc_archive 'CCDC 1982713'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;Spectropole RX   Universite Aix Marseille
France
;
_audit_update_record             
;
2020-02-07 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_audit_creation_date             2018-06-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13 N5 O2'
_chemical_formula_sum            'C12 H13 N5 O2'
_chemical_formula_weight         259.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c12 h13 n5 o2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.86080(10)
_cell_length_b                   24.6111(3)
_cell_length_c                   10.3984(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.7280(10)
_cell_angle_gamma                90
_cell_volume                     1217.99(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5652
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.9170
_cell_measurement_theta_min      4.6770
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.824
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0120
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7754
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.052
_diffrn_reflns_theta_min         3.592
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -13.00   1.00    1.00    --  -41.07 -57.00 -90.00   95
  2  ω    -53.00 -27.00   1.00    1.00    --  -41.07 -38.00 -60.00   26
  3  ω    -66.00  15.00   1.00    1.00    --  -41.07  38.00 -30.00   81
  4  ω    -72.00   2.00   1.00    1.00    --  -41.07  77.00 120.00   74
  5  ω    -83.00 -17.00   1.00    1.00    --  -41.07 -38.00  90.00   66
  6  ω     52.00 108.00   1.00   10.00    --  101.41 -94.00  60.00   56
  7  ω     83.00 110.00   1.00   10.00    --  101.41-125.00  30.00   27
  8  ω     68.00 127.00   1.00   10.00    --  101.41 -61.00-120.00   59
  9  ω     28.00  54.00   1.00   10.00    --  101.41-125.00  30.00   26
 10  ω     38.00 127.00   1.00   10.00    --  101.41 -45.00  60.00   89
 11  ω     33.00 128.00   1.00   10.00    --  101.41 -30.00-180.00   95
 12  ω    122.00 166.00   1.00   10.00    --  101.41  45.00   0.00   44
 13  ω     69.00 125.00   1.00   10.00    --  101.41  77.00 -30.00   56
 14  ω    153.00 178.00   1.00   10.00    --  101.41  77.00 -30.00   25
 15  ω     49.00 101.00   1.00   10.00    --  101.41 -94.00-180.00   52
 16  ω    135.00 175.00   1.00   10.00    --  101.41 125.00  30.00   40
 17  ω    120.00 165.00   1.00   10.00    --  101.41 125.00 120.00   45
 18  ω     25.00 115.00   1.00   10.00    --  101.41 -30.00 -30.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0776656000
_diffrn_orient_matrix_UB_12      -0.0502980000
_diffrn_orient_matrix_UB_13      0.0880800000
_diffrn_orient_matrix_UB_21      0.0139819000
_diffrn_orient_matrix_UB_22      0.0356394000
_diffrn_orient_matrix_UB_23      0.1229225000
_diffrn_orient_matrix_UB_31      -0.3139979000
_diffrn_orient_matrix_UB_32      -0.0108555000
_diffrn_orient_matrix_UB_33      -0.0044416000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2191
_reflns_number_total             2295
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0605P)²+0.3373P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1082
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C7(H7), C8(H8)
2.b X=CH2 refined with riding coordinates:
 N4(H4A,H4B)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2025(2) 0.48252(4) 0.38962(10) 0.0384(3) Uani 1 1 d . . . . .
O2 O 0.2651(3) 0.68482(4) 0.20266(10) 0.0525(3) Uani 1 1 d . . . . .
N1 N 0.1709(2) 0.56757(4) 0.45842(11) 0.0325(3) Uani 1 1 d . . . . .
H1 H 0.032831 0.556502 0.491772 0.039 Uiso 1 1 calc R . . . .
N2 N 0.3249(3) 0.65666(4) 0.41145(11) 0.0398(3) Uani 1 1 d . . . . .
N3 N 0.2404(3) 0.63030(5) 0.61765(11) 0.0376(3) Uani 1 1 d . . . . .
N4 N 0.4688(4) 0.71537(5) 0.63150(13) 0.0558(4) Uani 1 1 d . . . . .
H4A H 0.523386 0.743945 0.677212 0.067 Uiso 1 1 calc R . . . .
H4B H 0.508471 0.711467 0.555110 0.067 Uiso 1 1 calc R . . . .
N5 N 0.2634(3) 0.68406(5) 0.79799(12) 0.0436(3) Uani 1 1 d . . . . .
C1 C 0.2599(3) 0.62061(5) 0.49358(12) 0.0324(3) Uani 1 1 d . . . . .
C2 C 0.3232(3) 0.67728(5) 0.67886(13) 0.0372(3) Uani 1 1 d . . . . .
C3 C 0.2659(2) 0.53047(5) 0.38030(11) 0.0289(3) Uani 1 1 d . . . . .
C4 C 0.4439(2) 0.54635(5) 0.28566(12) 0.0289(3) Uani 1 1 d . . . . .
C5 C 0.5720(3) 0.50351(5) 0.23258(13) 0.0357(3) Uani 1 1 d . . . . .
H5 H 0.548297 0.468132 0.259847 0.043 Uiso 1 1 calc R . . . .
C6 C 0.7336(3) 0.51298(6) 0.14011(15) 0.0428(3) Uani 1 1 d . . . . .
H6 H 0.819819 0.484084 0.106264 0.051 Uiso 1 1 calc R . . . .
C7 C 0.7677(3) 0.56520(6) 0.09772(15) 0.0446(4) Uani 1 1 d . . . . .
H7 H 0.878407 0.571562 0.036092 0.053 Uiso 1 1 calc R . . . .
C8 C 0.6378(3) 0.60779(6) 0.14672(14) 0.0392(3) Uani 1 1 d . . . . .
H8 H 0.658648 0.642812 0.116501 0.047 Uiso 1 1 calc R . . . .
C9 C 0.4750(3) 0.59935(5) 0.24110(12) 0.0307(3) Uani 1 1 d . . . . .
C10 C 0.3385(3) 0.64855(5) 0.28391(13) 0.0352(3) Uani 1 1 d . . . . .
C11 C 0.0864(4) 0.64534(7) 0.84881(17) 0.0555(4) Uani 1 1 d . . . . .
H11A H 0.033107 0.616654 0.786141 0.083 Uiso 1 1 calc GR . . . .
H11B H -0.079078 0.663435 0.863988 0.083 Uiso 1 1 calc GR . . . .
H11C H 0.188192 0.630365 0.929862 0.083 Uiso 1 1 calc GR . . . .
C12 C 0.3506(5) 0.73227(7) 0.87631(16) 0.0577(5) Uani 1 1 d . . . . .
H12A H 0.541697 0.740842 0.872932 0.087 Uiso 1 1 calc GR . . . .
H12B H 0.336444 0.725621 0.965704 0.087 Uiso 1 1 calc GR . . . .
H12C H 0.231399 0.762204 0.842057 0.087 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.2285(15) . ?
O2 C10 1.2309(17) . ?
N1 H1 0.8600 . ?
N1 C1 1.4001(16) . ?
N1 C3 1.3635(16) . ?
N2 C1 1.3138(17) . ?
N2 C10 1.3560(18) . ?
N3 C1 1.3341(17) . ?
N3 C2 1.3415(17) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C2 1.3283(19) . ?
N5 C2 1.3392(18) . ?
N5 C11 1.453(2) . ?
N5 C12 1.4528(19) . ?
C3 C4 1.4886(17) . ?
C4 C5 1.3944(18) . ?
C4 C9 1.4025(17) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.380(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.374(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.3956(19) . ?
C9 C10 1.4918(18) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1 114.5 . . ?
C3 N1 H1 114.5 . . ?
C3 N1 C1 130.98(11) . . ?
C1 N2 C10 127.04(12) . . ?
C1 N3 C2 122.65(11) . . ?
H4A N4 H4B 120.0 . . ?
C2 N4 H4A 120.0 . . ?
C2 N4 H4B 120.0 . . ?
C2 N5 C11 120.70(13) . . ?
C2 N5 C12 121.79(13) . . ?
C12 N5 C11 117.30(13) . . ?
N2 C1 N1 124.21(12) . . ?
N2 C1 N3 125.56(12) . . ?
N3 C1 N1 109.90(11) . . ?
N4 C2 N3 124.29(13) . . ?
N4 C2 N5 119.16(13) . . ?
N5 C2 N3 116.47(12) . . ?
O1 C3 N1 118.39(11) . . ?
O1 C3 C4 119.55(11) . . ?
N1 C3 C4 122.05(11) . . ?
C5 C4 C3 115.43(11) . . ?
C5 C4 C9 119.05(12) . . ?
C9 C4 C3 125.37(12) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.77(13) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.16(13) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.88(13) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C9 121.07(13) . . ?
C9 C8 H8 119.5 . . ?
C4 C9 C10 124.88(12) . . ?
C8 C9 C4 119.04(12) . . ?
C8 C9 C10 116.05(11) . . ?
O2 C10 N2 119.98(13) . . ?
O2 C10 C9 117.92(12) . . ?
N2 C10 C9 121.63(12) . . ?
N5 C11 H11A 109.5 . . ?
N5 C11 H11B 109.5 . . ?
N5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N5 C12 H12A 109.5 . . ?
N5 C12 H12B 109.5 . . ?
N5 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.176
_oxdiff_exptl_absorpt_empirical_full_min 0.727
####################################################################### 
# 
# 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_mtf483
_database_code_depnum_ccdc_archive 'CCDC 1982714'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;Spectropole RX Universite Aix Marseille
France
;
_audit_update_record             
;
2020-02-07 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_audit_creation_date             2018-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H17 N5 O2'
_chemical_formula_sum            'C15 H17 N5 O2'
_chemical_formula_weight         299.33
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   24.9167(6)
_cell_length_b                   7.5596(2)
_cell_length_c                   15.5987(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.554(2)
_cell_angle_gamma                90
_cell_volume                     2897.42(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6579
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.8800
_cell_measurement_theta_min      3.5820
_shelx_estimated_absorpt_T_max   0.926
_shelx_estimated_absorpt_T_min   0.788
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11000
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.136
_diffrn_reflns_theta_min         3.598
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00  -8.00   1.00    5.00    --  -41.07 -77.00-180.00   59
  2  ω    -79.00 -40.00   1.00    5.00    --  -41.07 -57.00-180.00   39
  3  ω   -129.00  47.00   1.00    5.00    --  -41.07   0.00 -60.00  176
  4  ω    -69.00 -15.00   1.00    5.00    --  -41.07 -57.00-120.00   54
  5  ω    -50.00 -25.00   1.00    5.00    --  -41.07 -38.00 150.00   25
  6  ω     48.00  83.00   1.00    5.00    --   41.07-125.00-180.00   35
  7  ω     70.00  95.00   1.00   20.00    --  101.41  77.00-120.00   25
  8  ω    116.00 177.00   1.00   20.00    --  101.41  77.00-150.00   61
  9  ω    115.00 172.00   1.00   20.00    --  101.41  45.00 -60.00   57
 10  ω     48.00  93.00   1.00   20.00    --  101.41 -94.00-150.00   45
 11  ω     72.00  99.00   1.00   20.00    --  101.41  61.00 150.00   27
 12  ω     77.00 102.00   1.00   20.00    --  101.41  45.00-120.00   25
 13  ω     69.00  95.00   1.00   20.00    --  101.41  77.00-180.00   26
 14  ω    107.00 172.00   1.00   20.00    --  101.41  77.00-180.00   65
 15  ω    108.00 140.00   1.00   20.00    --  101.41  77.00 150.00   32
 16  ω     70.00  95.00   1.00   20.00    --  101.41  77.00-150.00   25
 17  ω     73.00 108.00   1.00   20.00    --  101.41  61.00-120.00   35
 18  ω     30.00 129.00   1.00   20.00    --  101.41 -61.00-120.00   99
 19  ω     72.00 117.00   1.00   20.00    --  101.41  61.00-180.00   45
 20  ω     74.00 101.00   1.00   20.00    --  101.41  61.00-150.00   27
 21  ω     74.00 101.00   1.00   20.00    --  101.41  61.00 -90.00   27
 22  ω     69.00  95.00   1.00   20.00    --  101.41  77.00 150.00   26
 23  ω    152.00 178.00   1.00   20.00    --  101.41  77.00 -90.00   26
 24  ω     70.00 108.00   1.00   20.00    --  101.41  77.00 -90.00   38
 25  ω    108.00 177.00   1.00   20.00    --  101.41  77.00-120.00   69
 26  ω     79.00 106.00   1.00   20.00    --  101.41  45.00 -90.00   27
 27  ω     76.00 103.00   1.00   20.00    --  101.41  45.00-150.00   27
 28  ω     19.00 101.00   1.00   20.00    --  101.41 -94.00  30.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0557729000
_diffrn_orient_matrix_UB_12      0.0406915000
_diffrn_orient_matrix_UB_13      -0.0257954000
_diffrn_orient_matrix_UB_21      0.0235106000
_diffrn_orient_matrix_UB_22      0.0390336000
_diffrn_orient_matrix_UB_23      0.0957560000
_diffrn_orient_matrix_UB_31      0.0163166000
_diffrn_orient_matrix_UB_32      -0.1959091000
_diffrn_orient_matrix_UB_33      0.0138049000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2510
_reflns_number_total             2758
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2758
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0474P)²+1.7395P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1021
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2.a Riding coordinates:
 N4(H4A,H4B)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C7(H7), C8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.73033(4) 0.04935(16) 0.45238(9) 0.0597(3) Uani 1 1 d . . . . .
O2 O 0.51521(4) 0.17337(16) 0.38612(9) 0.0639(4) Uani 1 1 d . . . . .
N1 N 0.67277(4) 0.22866(15) 0.50374(8) 0.0400(3) Uani 1 1 d . . . . .
H1 H 0.699695 0.301340 0.511159 0.048 Uiso 1 1 calc R . . . .
N2 N 0.57620(4) 0.25725(15) 0.50010(8) 0.0383(3) Uani 1 1 d . . . . .
N3 N 0.64255(4) 0.40656(15) 0.59904(8) 0.0372(3) Uani 1 1 d . . . . .
N4 N 0.55508(4) 0.52618(17) 0.60156(9) 0.0467(3) Uani 1 1 d . . . . .
H4A H 0.542583 0.447673 0.558270 0.056 Uiso 1 1 d R . . . .
H4B H 0.534783 0.623073 0.607370 0.056 Uiso 1 1 d R . . . .
N5 N 0.63158(4) 0.63144(16) 0.69169(8) 0.0407(3) Uani 1 1 d . . . . .
C1 C 0.62662(5) 0.29328(17) 0.53462(9) 0.0336(3) Uani 1 1 d . . . . .
C2 C 0.60847(5) 0.52049(17) 0.62906(9) 0.0342(3) Uani 1 1 d . . . . .
C3 C 0.68363(5) 0.07575(18) 0.46475(9) 0.0375(3) Uani 1 1 d . . . . .
C4 C 0.64113(5) -0.06069(17) 0.43832(8) 0.0339(3) Uani 1 1 d . . . . .
C5 C 0.66088(6) -0.22758(19) 0.42126(10) 0.0436(3) Uani 1 1 d . . . . .
H5 H 0.698232 -0.247490 0.430591 0.052 Uiso 1 1 calc R . . . .
C6 C 0.62605(7) -0.3629(2) 0.39090(12) 0.0531(4) Uani 1 1 d . . . . .
H6 H 0.639802 -0.473691 0.380233 0.064 Uiso 1 1 calc R . . . .
C7 C 0.57071(7) -0.3340(2) 0.37633(13) 0.0581(4) Uani 1 1 d . . . . .
H7 H 0.547052 -0.425276 0.355546 0.070 Uiso 1 1 calc R . . . .
C8 C 0.55038(6) -0.1703(2) 0.39248(12) 0.0503(4) Uani 1 1 d . . . . .
H8 H 0.512956 -0.151960 0.382204 0.060 Uiso 1 1 calc R . . . .
C9 C 0.58500(5) -0.03145(17) 0.42401(9) 0.0358(3) Uani 1 1 d . . . . .
C10 C 0.55810(5) 0.14272(18) 0.43478(10) 0.0392(3) Uani 1 1 d . . . . .
C11 C 0.60211(6) 0.77006(19) 0.72962(10) 0.0421(3) Uani 1 1 d . . . . .
H11A H 0.612138 0.767932 0.792415 0.050 Uiso 1 1 calc R . . . .
H11B H 0.563282 0.748430 0.715234 0.050 Uiso 1 1 calc R . . . .
C12 C 0.61517(6) 0.9495(2) 0.69564(11) 0.0498(4) Uani 1 1 d . . . . .
H12A H 0.597113 1.040605 0.724169 0.060 Uiso 1 1 calc R . . . .
H12B H 0.601543 0.955818 0.633738 0.060 Uiso 1 1 calc R . . . .
C13 C 0.67631(7) 0.9830(2) 0.71191(11) 0.0515(4) Uani 1 1 d . . . . .
H13A H 0.688870 0.997071 0.773799 0.062 Uiso 1 1 calc R . . . .
H13B H 0.684014 1.091703 0.683258 0.062 Uiso 1 1 calc R . . . .
C14 C 0.70677(6) 0.8304(2) 0.67789(11) 0.0502(4) Uani 1 1 d . . . . .
H14A H 0.699022 0.829693 0.614863 0.060 Uiso 1 1 calc R . . . .
H14B H 0.745611 0.847811 0.695444 0.060 Uiso 1 1 calc R . . . .
C15 C 0.69069(5) 0.6542(2) 0.71186(10) 0.0457(4) Uani 1 1 d . . . . .
H15A H 0.708485 0.559397 0.685450 0.055 Uiso 1 1 calc R . . . .
H15B H 0.702448 0.648758 0.774277 0.055 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.2270(16) . ?
O2 C10 1.2257(17) . ?
N1 H1 0.8600 . ?
N1 C1 1.4059(16) . ?
N1 C3 1.3543(17) . ?
N2 C1 1.3109(17) . ?
N2 C10 1.3559(18) . ?
N3 C1 1.3297(17) . ?
N3 C2 1.3470(16) . ?
N4 H4A 0.9140 . ?
N4 H4B 0.9032 . ?
N4 C2 1.3288(17) . ?
N5 C2 1.3427(17) . ?
N5 C11 1.4601(17) . ?
N5 C15 1.4642(17) . ?
C3 C4 1.4868(18) . ?
C4 C5 1.3957(19) . ?
C4 C9 1.3969(18) . ?
C5 H5 0.9300 . ?
C5 C6 1.374(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.377(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.376(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.3955(19) . ?
C9 C10 1.4995(18) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.512(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.523(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.524(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.512(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 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
C1 N1 H1 113.3 . . ?
C3 N1 H1 113.3 . . ?
C3 N1 C1 133.33(11) . . ?
C1 N2 C10 128.17(11) . . ?
C1 N3 C2 123.25(11) . . ?
H4A N4 H4B 118.2 . . ?
C2 N4 H4A 114.7 . . ?
C2 N4 H4B 122.8 . . ?
C2 N5 C11 124.00(11) . . ?
C2 N5 C15 121.64(11) . . ?
C11 N5 C15 112.59(11) . . ?
N2 C1 N1 124.73(12) . . ?
N2 C1 N3 126.14(11) . . ?
N3 C1 N1 108.92(11) . . ?
N4 C2 N3 124.30(12) . . ?
N4 C2 N5 120.02(11) . . ?
N5 C2 N3 115.68(11) . . ?
O1 C3 N1 118.36(12) . . ?
O1 C3 C4 119.60(12) . . ?
N1 C3 C4 122.03(11) . . ?
C5 C4 C3 114.99(12) . . ?
C5 C4 C9 119.21(12) . . ?
C9 C4 C3 125.64(12) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.09(13) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.77(14) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.09(14) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C9 121.08(14) . . ?
C9 C8 H8 119.5 . . ?
C4 C9 C10 125.13(12) . . ?
C8 C9 C4 118.76(13) . . ?
C8 C9 C10 116.01(12) . . ?
O2 C10 N2 119.45(12) . . ?
O2 C10 C9 117.17(12) . . ?
N2 C10 C9 123.08(12) . . ?
N5 C11 H11A 109.6 . . ?
N5 C11 H11B 109.6 . . ?
N5 C11 C12 110.49(12) . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C11 C12 C13 110.98(12) . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C12 C13 C14 111.01(13) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 C13 111.62(13) . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
N5 C15 C14 110.12(12) . . ?
N5 C15 H15A 109.6 . . ?
N5 C15 H15B 109.6 . . ?
C14 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C4 C5 15.5(2) . . . . ?
O1 C3 C4 C9 -159.83(15) . . . . ?
N1 C3 C4 C5 -163.34(13) . . . . ?
N1 C3 C4 C9 21.3(2) . . . . ?
N5 C11 C12 C13 -55.53(16) . . . . ?
C1 N1 C3 O1 -173.01(15) . . . . ?
C1 N1 C3 C4 5.9(2) . . . . ?
C1 N2 C10 O2 -149.35(16) . . . . ?
C1 N2 C10 C9 37.2(2) . . . . ?
C1 N3 C2 N4 3.9(2) . . . . ?
C1 N3 C2 N5 -177.04(13) . . . . ?
C2 N3 C1 N1 164.46(12) . . . . ?
C2 N3 C1 N2 -10.4(2) . . . . ?
C2 N5 C11 C12 -105.01(16) . . . . ?
C2 N5 C15 C14 106.09(15) . . . . ?
C3 N1 C1 N2 -32.6(2) . . . . ?
C3 N1 C1 N3 152.40(15) . . . . ?
C3 C4 C5 C6 -175.82(15) . . . . ?
C3 C4 C9 C8 174.78(14) . . . . ?
C3 C4 C9 C10 -1.3(2) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C4 C9 C10 O2 147.40(15) . . . . ?
C4 C9 C10 N2 -39.0(2) . . . . ?
C5 C4 C9 C8 -0.4(2) . . . . ?
C5 C4 C9 C10 -176.52(13) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C7 C8 C9 C4 0.6(2) . . . . ?
C7 C8 C9 C10 177.07(15) . . . . ?
C8 C9 C10 O2 -28.8(2) . . . . ?
C8 C9 C10 N2 144.74(15) . . . . ?
C9 C4 C5 C6 -0.1(2) . . . . ?
C10 N2 C1 N1 6.1(2) . . . . ?
C10 N2 C1 N3 -179.76(14) . . . . ?
C11 N5 C2 N3 176.92(13) . . . . ?
C11 N5 C2 N4 -4.0(2) . . . . ?
C11 N5 C15 C14 -59.35(16) . . . . ?
C11 C12 C13 C14 51.98(18) . . . . ?
C12 C13 C14 C15 -51.88(18) . . . . ?
C13 C14 C15 N5 54.71(16) . . . . ?
C15 N5 C2 N3 13.2(2) . . . . ?
C15 N5 C2 N4 -167.75(14) . . . . ?
C15 N5 C11 C12 60.02(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.048
_oxdiff_exptl_absorpt_empirical_full_min 0.709
####################################################################### 
# 
# 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_mtf487
_database_code_depnum_ccdc_archive 'CCDC 1982715'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;Spectropole RX Universite Aix Marseille
France
;
_audit_update_record             
;
2020-02-07 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_audit_creation_date             2018-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 N6 O2, C3 H6 O'
_chemical_formula_sum            'C26 H26 N6 O3'
_chemical_formula_weight         470.53
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c23 h20 n6 o2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2690(4)
_cell_length_b                   10.7223(5)
_cell_length_c                   12.4618(5)
_cell_angle_alpha                105.159(4)
_cell_angle_beta                 98.990(3)
_cell_angle_gamma                102.897(4)
_cell_volume                     1256.94(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6946
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.7740
_cell_measurement_theta_min      3.9100
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.811
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18793
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.811
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.105
_diffrn_reflns_theta_min         3.009
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.811
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00 -38.00   1.00   17.50    --   -7.78 153.00 -20.78   45
  2  ω    -16.00  79.00   1.00   17.50    --    8.41  77.00  60.00   95
  3  ω    -16.00  74.00   1.00   17.50    --    8.41  38.00 -30.00   90
  4  ω    -55.00  37.00   1.00   17.50    --    8.41 -57.00 150.00   92
  5  ω    -29.00  83.00   1.00   17.50    --    8.41  19.00-120.00  112
  6  ω    -37.00  42.00   1.00   17.50    --   10.00 -73.00-103.40   79
  7  ω      1.00  48.00   1.00   17.50    --   10.00 -91.00  14.66   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0393009000
_diffrn_orient_matrix_UB_12      -0.0291946000
_diffrn_orient_matrix_UB_13      -0.0361348000
_diffrn_orient_matrix_UB_21      0.0587665000
_diffrn_orient_matrix_UB_22      0.0544659000
_diffrn_orient_matrix_UB_23      0.0300381000
_diffrn_orient_matrix_UB_31      0.0172817000
_diffrn_orient_matrix_UB_32      -0.0356189000
_diffrn_orient_matrix_UB_33      0.0382144000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4065
_reflns_number_total             5472
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.66
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5472
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0641
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0710P)²+0.7242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1659
_refine_ls_wR_factor_ref         0.1803
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Restrained distances
 C18-C24
 1.39 with sigma of 0.01
 C24-C25
 1.39 with sigma of 0.01
 C25-C26
 1.39 with sigma of 0.01
 C26-C27
 1.39 with sigma of 0.01
 C27-C28
 1.39 with sigma of 0.01
 C28-C18
 1.39 with sigma of 0.01
 C29-O3
 1.2 with sigma of 0.005
 C30-O4
 1.2 with sigma of 0.005
 C29-C31
 1.45 with sigma of 0.005
 C29-C32
 1.45 with sigma of 0.005
 C30-C32
 1.45 with sigma of 0.005
 C30-C31
 1.45 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(C29) = Uanis(C30)
4. Rigid body (RIGU) restrains
 C18, C19, C20, C21, C22, C23
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C18, C24, C25, C26, C27, C28
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: C19(0.5) H19(0.5) C20(0.5) H20(0.5) C21(0.5) H21(0.5) C22(0.5)
 H22(0.5) C23(0.5) H23(0.5) C24(0.5) H24(0.5) C25(0.5) H25(0.5) C26(0.5)
 H26(0.5) C27(0.5) H27(0.5) C28(0.5) H28(0.5) O3(0.75) O4(0.25) C29(0.75)
 C30(0.25) H31A(0.75) H31B(0.75) H31C(0.75) H31D(0.25) H31E(0.25) H31F(0.25)
 H32A(0.75) H32B(0.75) H32C(0.75) H32D(0.25) H32E(0.25) H32F(0.25)
6.a Riding coordinates:
 N4(H4A,H4B)
6.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C17(H17A,H17B)
6.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26), C27(H27), C28(H28)
6.d Fitted hexagon refined as free rotating group:
 C18(C19,C20,C21,C22,C23)
6.e Idealised Me refined with riding coordinates:
 C31(H31A,H31B,H31C), C31(H31D,H31E,H31F), C32(H32A,H32B,H32C), C32(H32D,H32E,
 H32F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.38993(17) 0.5579(2) 0.41756(18) 0.0702(6) Uani 1 1 d . . . . .
O2 O -0.04534(18) 0.13598(16) 0.30077(14) 0.0607(5) Uani 1 1 d . . . . .
N1 N 0.32028(17) 0.38461(19) 0.48154(16) 0.0469(5) Uani 1 1 d . . . . .
H1 H 0.405092 0.384772 0.494097 0.056 Uiso 1 1 calc R . . . .
N2 N 0.11060(17) 0.22195(17) 0.46776(14) 0.0417(4) Uani 1 1 d . . . . .
N3 N 0.31055(17) 0.28149(17) 0.61410(14) 0.0415(4) Uani 1 1 d . . . . .
N4 N 0.13719(18) 0.11243(18) 0.63953(16) 0.0470(5) Uani 1 1 d . . . . .
H4A H 0.107282 0.039058 0.668029 0.056 Uiso 1 1 d R . . . .
H4B H 0.080482 0.107558 0.569529 0.056 Uiso 1 1 d R . . . .
N5 N 0.35334(17) 0.19476(18) 0.75988(15) 0.0440(4) Uani 1 1 d . . . . .
N6 N -0.09278(19) 0.3810(2) 0.32263(18) 0.0563(5) Uani 1 1 d . . . . .
C1 C 0.2368(2) 0.2922(2) 0.52064(17) 0.0383(4) Uani 1 1 d . . . . .
C2 C 0.2637(2) 0.1942(2) 0.66857(16) 0.0377(4) Uani 1 1 d . . . . .
C3 C 0.2935(2) 0.4743(2) 0.42750(19) 0.0458(5) Uani 1 1 d . . . . .
C4 C 0.1512(2) 0.4762(2) 0.38465(17) 0.0413(5) Uani 1 1 d . . . . .
C5 C 0.1375(3) 0.5920(2) 0.3590(2) 0.0526(6) Uani 1 1 d . . . . .
H5 H 0.214604 0.662934 0.370607 0.063 Uiso 1 1 calc R . . . .
C6 C 0.0103(3) 0.6010(3) 0.3168(2) 0.0630(7) Uani 1 1 d . . . . .
H6 H -0.000583 0.677132 0.298202 0.076 Uiso 1 1 calc R . . . .
C7 C -0.1011(3) 0.4953(3) 0.3024(2) 0.0628(7) Uani 1 1 d . . . . .
H7 H -0.187830 0.503855 0.277028 0.075 Uiso 1 1 calc R . . . .
C8 C 0.0332(2) 0.3714(2) 0.36305(17) 0.0407(5) Uani 1 1 d . . . . .
C9 C 0.0337(2) 0.2351(2) 0.37440(17) 0.0419(5) Uani 1 1 d . . . . .
C10 C 0.3103(2) 0.1235(2) 0.83916(19) 0.0495(5) Uani 1 1 d . . . . .
H10A H 0.390717 0.112056 0.883584 0.059 Uiso 1 1 calc R . . . .
H10B H 0.250798 0.034711 0.795638 0.059 Uiso 1 1 calc R . . . .
C11 C 0.2358(2) 0.1947(2) 0.91977(18) 0.0525(6) Uani 1 1 d . . . . .
C12 C 0.1749(3) 0.1287(3) 0.9890(2) 0.0759(8) Uani 1 1 d . . . . .
H12 H 0.179227 0.041552 0.983402 0.091 Uiso 1 1 calc R . . . .
C13 C 0.1082(4) 0.1901(5) 1.0656(3) 0.1020(13) Uani 1 1 d . . . . .
H13 H 0.068969 0.144829 1.112026 0.122 Uiso 1 1 calc R . . . .
C14 C 0.0995(4) 0.3171(5) 1.0737(3) 0.1049(13) Uani 1 1 d . . . . .
H14 H 0.053400 0.358062 1.124862 0.126 Uiso 1 1 calc R . . . .
C15 C 0.1586(4) 0.3840(4) 1.0065(3) 0.0970(11) Uani 1 1 d . . . . .
H15 H 0.152730 0.470747 1.012196 0.116 Uiso 1 1 calc R . . . .
C16 C 0.2272(3) 0.3236(3) 0.9300(2) 0.0714(8) Uani 1 1 d . . . . .
H16 H 0.267905 0.370392 0.885117 0.086 Uiso 1 1 calc R . . . .
C17 C 0.4972(2) 0.2755(2) 0.7909(2) 0.0488(5) Uani 1 1 d . . . . .
H17A H 0.521984 0.324183 0.871900 0.059 Uiso 1 1 calc R . . . .
H17B H 0.507208 0.340986 0.749678 0.059 Uiso 1 1 calc R . . . .
C18 C 0.5942(2) 0.1903(2) 0.76428(19) 0.0548(5) Uani 1 1 d D U . . .
C19 C 0.7204(4) 0.2203(5) 0.8391(4) 0.065(2) Uani 0.5 1 d G U P A 1
H19 H 0.747673 0.295905 0.903247 0.077 Uiso 0.5 1 calc R . P A 1
C20 C 0.8059(5) 0.1372(7) 0.8180(6) 0.100(4) Uani 0.5 1 d G U P A 1
H20 H 0.890400 0.157288 0.868001 0.120 Uiso 0.5 1 calc R . P A 1
C21 C 0.7652(6) 0.0242(7) 0.7220(6) 0.093(3) Uani 0.5 1 d G U P A 1
H21 H 0.822448 -0.031348 0.707915 0.111 Uiso 0.5 1 calc R . P A 1
C22 C 0.6390(7) -0.0058(5) 0.6472(5) 0.108(3) Uani 0.5 1 d G U P A 1
H22 H 0.611769 -0.081370 0.583073 0.130 Uiso 0.5 1 calc R . P A 1
C23 C 0.5535(4) 0.0773(4) 0.6684(3) 0.084(2) Uani 0.5 1 d G U P A 1
H23 H 0.469039 0.057245 0.618317 0.101 Uiso 0.5 1 calc R . P A 1
C24 C 0.6979(6) 0.1893(8) 0.8475(6) 0.0547(15) Uani 0.5 1 d D U P A 2
H24 H 0.703354 0.233134 0.923767 0.066 Uiso 0.5 1 calc R . P A 2
C25 C 0.7955(8) 0.1223(10) 0.8178(9) 0.088(3) Uani 0.5 1 d D U P A 2
H25 H 0.864722 0.120427 0.874725 0.105 Uiso 0.5 1 calc R . P A 2
C26 C 0.7902(9) 0.0595(8) 0.7055(8) 0.087(2) Uani 0.5 1 d D U P A 2
H26 H 0.856800 0.017168 0.686181 0.104 Uiso 0.5 1 calc R . P A 2
C27 C 0.6879(7) 0.0593(7) 0.6234(8) 0.091(2) Uani 0.5 1 d D U P A 2
H27 H 0.679307 0.010884 0.547734 0.109 Uiso 0.5 1 calc R . P A 2
C28 C 0.5959(6) 0.1313(7) 0.6521(5) 0.0702(16) Uani 0.5 1 d D U P A 2
H28 H 0.533169 0.140242 0.594109 0.084 Uiso 0.5 1 calc R . P A 2
O3 O 0.5919(5) 0.3581(4) 0.0951(4) 0.1374(16) Uani 0.75 1 d D . P B 1
O4 O 0.553(2) 0.1946(17) 0.2925(11) 0.182(7) Uani 0.25 1 d D . P C 2
C29 C 0.5563(4) 0.2846(4) 0.1508(3) 0.0855(13) Uani 0.75 1 d D . P B 1
C30 C 0.5216(12) 0.2193(9) 0.2057(8) 0.0855(13) Uani 0.25 1 d D . P C 2
C31 C 0.4910(7) 0.3460(6) 0.2340(6) 0.206(4) Uani 1 1 d D . . . .
H31A H 0.553596 0.428693 0.284352 0.310 Uiso 0.75 1 calc R . P B 1
H31B H 0.463845 0.286556 0.277311 0.310 Uiso 0.75 1 calc R . P B 1
H31C H 0.411430 0.364159 0.196760 0.310 Uiso 0.75 1 calc R . P B 1
H31D H 0.413528 0.339113 0.268618 0.310 Uiso 0.25 1 calc R . P B 2
H31E H 0.470010 0.370567 0.165944 0.310 Uiso 0.25 1 calc R . P B 2
H31F H 0.568918 0.413313 0.286621 0.310 Uiso 0.25 1 calc R . P B 2
C32 C 0.5752(6) 0.1542(4) 0.1158(5) 0.149(2) Uani 1 1 d D . . . .
H32A H 0.524191 0.108050 0.038654 0.223 Uiso 0.75 1 calc R . P B 1
H32B H 0.543199 0.104718 0.165069 0.223 Uiso 0.75 1 calc R . P B 1
H32C H 0.670837 0.161587 0.120001 0.223 Uiso 0.75 1 calc R . P B 1
H32D H 0.673216 0.176705 0.139879 0.223 Uiso 0.25 1 calc R . P B 2
H32E H 0.551151 0.183070 0.050521 0.223 Uiso 0.25 1 calc R . P B 2
H32F H 0.537428 0.058643 0.096005 0.223 Uiso 0.25 1 calc R . P B 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
O1 C3 1.224(3) . ?
O2 C9 1.226(3) . ?
N1 H1 0.8600 . ?
N1 C1 1.400(3) . ?
N1 C3 1.362(3) . ?
N2 C1 1.311(3) . ?
N2 C9 1.358(3) . ?
N3 C1 1.333(2) . ?
N3 C2 1.342(3) . ?
N4 H4A 0.9548 . ?
N4 H4B 0.9522 . ?
N4 C2 1.329(3) . ?
N5 C2 1.345(2) . ?
N5 C10 1.461(3) . ?
N5 C17 1.469(3) . ?
N6 C7 1.332(3) . ?
N6 C8 1.349(3) . ?
C3 C4 1.482(3) . ?
C4 C5 1.391(3) . ?
C4 C8 1.391(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.364(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.370(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.507(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.509(4) . ?
C11 C12 1.388(3) . ?
C11 C16 1.378(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.375(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.363(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.364(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(4) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.512(3) . ?
C18 C19 1.3900 . ?
C18 C23 1.3900 . ?
C18 C24 1.369(6) . ?
C18 C28 1.381(6) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C31 H31D 0.9600 . ?
C31 H31E 0.9600 . ?
C31 H31F 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C32 H32D 0.9600 . ?
C32 H32E 0.9600 . ?
C32 H32F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1 113.7 . . ?
C3 N1 H1 113.7 . . ?
C3 N1 C1 132.57(18) . . ?
C1 N2 C9 126.96(17) . . ?
C1 N3 C2 123.67(17) . . ?
H4A N4 H4B 114.7 . . ?
C2 N4 H4A 125.3 . . ?
C2 N4 H4B 117.0 . . ?
C2 N5 C10 121.72(17) . . ?
C2 N5 C17 122.06(17) . . ?
C10 N5 C17 116.04(16) . . ?
C7 N6 C8 117.5(2) . . ?
N2 C1 N1 124.56(17) . . ?
N2 C1 N3 126.76(18) . . ?
N3 C1 N1 108.50(17) . . ?
N3 C2 N5 115.69(18) . . ?
N4 C2 N3 124.58(17) . . ?
N4 C2 N5 119.71(18) . . ?
O1 C3 N1 118.81(19) . . ?
O1 C3 C4 119.55(19) . . ?
N1 C3 C4 121.60(18) . . ?
C5 C4 C3 115.83(19) . . ?
C5 C4 C8 118.0(2) . . ?
C8 C4 C3 126.05(18) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 120.7 . . ?
C5 C6 C7 118.5(2) . . ?
C7 C6 H6 120.7 . . ?
N6 C7 C6 123.9(2) . . ?
N6 C7 H7 118.0 . . ?
C6 C7 H7 118.0 . . ?
N6 C8 C4 122.24(19) . . ?
N6 C8 C9 113.73(18) . . ?
C4 C8 C9 123.91(18) . . ?
O2 C9 N2 120.60(19) . . ?
O2 C9 C8 117.85(18) . . ?
N2 C9 C8 121.33(18) . . ?
N5 C10 H10A 108.8 . . ?
N5 C10 H10B 108.8 . . ?
N5 C10 C11 113.59(18) . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C12 C11 C10 118.6(2) . . ?
C16 C11 C10 123.3(2) . . ?
C16 C11 C12 118.0(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.9(4) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.4(4) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 120.5(3) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
N5 C17 H17A 109.1 . . ?
N5 C17 H17B 109.1 . . ?
N5 C17 C18 112.38(19) . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C4 C5 -14.1(3) . . . . ?
O1 C3 C4 C8 162.6(2) . . . . ?
N1 C3 C4 C5 163.6(2) . . . . ?
N1 C3 C4 C8 -19.7(3) . . . . ?
N5 C10 C11 C12 171.9(2) . . . . ?
N5 C10 C11 C16 -9.4(3) . . . . ?
N6 C8 C9 O2 37.5(3) . . . . ?
N6 C8 C9 N2 -137.1(2) . . . . ?
C1 N1 C3 O1 169.3(2) . . . . ?
C1 N1 C3 C4 -8.4(4) . . . . ?
C1 N2 C9 O2 143.5(2) . . . . ?
C1 N2 C9 C8 -42.1(3) . . . . ?
C1 N3 C2 N4 -3.1(3) . . . . ?
C1 N3 C2 N5 178.36(19) . . . . ?
C2 N3 C1 N1 -175.35(18) . . . . ?
C2 N3 C1 N2 0.0(3) . . . . ?
C2 N5 C10 C11 -76.2(3) . . . . ?
C2 N5 C17 C18 -106.5(2) . . . . ?
C3 N1 C1 N2 37.3(4) . . . . ?
C3 N1 C1 N3 -147.3(2) . . . . ?
C3 C4 C5 C6 178.6(2) . . . . ?
C3 C4 C8 N6 -179.2(2) . . . . ?
C3 C4 C8 C9 -3.5(3) . . . . ?
C4 C5 C6 C7 0.9(4) . . . . ?
C4 C8 C9 O2 -138.5(2) . . . . ?
C4 C8 C9 N2 46.9(3) . . . . ?
C5 C4 C8 N6 -2.5(3) . . . . ?
C5 C4 C8 C9 173.1(2) . . . . ?
C5 C6 C7 N6 -3.0(4) . . . . ?
C7 N6 C8 C4 0.7(3) . . . . ?
C7 N6 C8 C9 -175.4(2) . . . . ?
C8 N6 C7 C6 2.1(4) . . . . ?
C8 C4 C5 C6 1.7(3) . . . . ?
C9 N2 C1 N1 -7.4(3) . . . . ?
C9 N2 C1 N3 178.0(2) . . . . ?
C10 N5 C2 N3 168.91(19) . . . . ?
C10 N5 C2 N4 -9.7(3) . . . . ?
C10 N5 C17 C18 78.3(2) . . . . ?
C10 C11 C12 C13 178.6(3) . . . . ?
C10 C11 C16 C15 -179.3(3) . . . . ?
C11 C12 C13 C14 0.8(5) . . . . ?
C12 C11 C16 C15 -0.6(4) . . . . ?
C12 C13 C14 C15 -0.8(6) . . . . ?
C13 C14 C15 C16 0.1(6) . . . . ?
C14 C15 C16 C11 0.6(5) . . . . ?
C16 C11 C12 C13 -0.1(4) . . . . ?
C17 N5 C2 N3 -6.0(3) . . . . ?
C17 N5 C2 N4 175.34(19) . . . . ?
C17 N5 C10 C11 99.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.432
_oxdiff_exptl_absorpt_empirical_full_min 0.591
