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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1584768'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H31 F5 N6 O3'
_chemical_formula_weight         426.45

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'
F F 0.0171 0.0103 '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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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'
'-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                   12.1360(5)
_cell_length_b                   8.6567(4)
_cell_length_c                   19.1395(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.145(4)
_cell_angle_gamma                90
_cell_volume                     2009.34(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293
_cell_measurement_reflns_used    2885
_cell_measurement_theta_min      4.7020
_cell_measurement_theta_max      28.2680

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.130
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.97758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.4547
_diffrn_reflns_number            8190
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.262
_diffrn_reflns_theta_max         29.264
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2418
_reflns_number_gt                1861
_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.9'
_computing_publication_material  'PARST93 (Nardelli, 1993)'
_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)+(0.0606P)²+2.2889P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2418
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1356
_refine_ls_wR_factor_gt          0.1242
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
F2 F 0.40075(10) 0.08514(16) 0.60309(6) 0.0470(3) Uani 1 1 d . . . . .
F3 F 0.5000 0.6782(2) 0.7500 0.0573(5) Uani 1 2 d S T P . .
O1 O 0.21475(12) 0.72552(15) 0.70687(7) 0.0403(3) Uani 1 1 d . . . . .
F1 F 0.37828(11) 0.34605(17) 0.61495(10) 0.0697(5) Uani 1 1 d . . . . .
N3 N 0.18044(11) 0.46173(15) 0.61811(7) 0.0226(3) Uani 1 1 d . . . . .
H3 H 0.2550 0.4182 0.6208 0.027 Uiso 1 1 calc R U . . .
N1 N 0.04569(12) -0.13526(17) 0.48019(8) 0.0328(4) Uani 1 1 d . . . . .
N2 N 0.10304(12) -0.04189(17) 0.52279(8) 0.0331(4) Uani 1 1 d . . . . .
C1 C 0.05514(14) 0.09021(19) 0.54132(9) 0.0269(4) Uani 1 1 d . . . . .
C3 C 0.11052(14) 0.36209(19) 0.57005(8) 0.0264(4) Uani 1 1 d . . . . .
H3A H 0.1343 0.3740 0.5225 0.032 Uiso 1 1 calc R U . . .
H3B H 0.0343 0.3952 0.5713 0.032 Uiso 1 1 calc R U . . .
C7 C 0.13860(14) 0.46833(19) 0.69066(8) 0.0257(3) Uani 1 1 d . . . . .
H7A H 0.1387 0.3655 0.7108 0.031 Uiso 1 1 calc R U . . .
H7B H 0.0634 0.5066 0.6892 0.031 Uiso 1 1 calc R U . . .
C2 C 0.11900(15) 0.19300(19) 0.59123(9) 0.0303(4) Uani 1 1 d . . . . .
H2A H 0.1959 0.1621 0.5928 0.036 Uiso 1 1 calc R U . . .
H2B H 0.0912 0.1805 0.6378 0.036 Uiso 1 1 calc R U . . .
C4 C 0.18750(14) 0.62301(19) 0.59009(9) 0.0281(4) Uani 1 1 d . . . . .
H4A H 0.1142 0.6674 0.5855 0.034 Uiso 1 1 calc R U . . .
H4B H 0.2187 0.6211 0.5442 0.034 Uiso 1 1 calc R U . . .
C6 C 0.21105(16) 0.5736(2) 0.73527(9) 0.0349(4) Uani 1 1 d . . . . .
H6A H 0.1831 0.5783 0.7820 0.042 Uiso 1 1 calc R U . . .
H6B H 0.2851 0.5315 0.7387 0.042 Uiso 1 1 calc R U . . .
C5 C 0.25874(16) 0.7205(2) 0.63896(10) 0.0363(4) Uani 1 1 d . . . . .
H5A H 0.3327 0.6778 0.6421 0.044 Uiso 1 1 calc R U . . .
H5B H 0.2634 0.8245 0.6205 0.044 Uiso 1 1 calc R U . . .
O2 O 0.5189(3) 0.4199(5) 0.7130(3) 0.107(2) Uani 0.5 1 d . . P . .
H1 H 0.386(3) 0.213(5) 0.607(2) 0.118(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 C5 1.424(2) . ?
O1 C6 1.424(2) . ?
N3 C7 1.497(2) . ?
N3 C3 1.501(2) . ?
N3 C4 1.499(2) . ?
N1 N2 1.327(2) . ?
N1 C1 1.335(2) 5_556 ?
N2 C1 1.337(2) . ?
C1 N1 1.335(2) 5_556 ?
C1 C2 1.500(2) . ?
C3 C2 1.521(2) . ?
C7 C6 1.509(2) . ?
C4 C5 1.508(2) . ?
O2 O2 1.506(12) 2_656 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C6 109.77(14) . . ?
C7 N3 C3 112.75(13) . . ?
C7 N3 C4 108.79(12) . . ?
C3 N3 C4 110.77(12) . . ?
N2 N1 C1 117.74(14) . 5_556 ?
N1 N2 C1 117.44(14) . . ?
N1 C1 N2 124.82(15) 5_556 . ?
N1 C1 C2 117.97(14) 5_556 . ?
N2 C1 C2 117.19(15) . . ?
N3 C3 C2 111.02(12) . . ?
N3 C7 C6 109.70(14) . . ?
C1 C2 C3 111.90(13) . . ?
N3 C4 C5 109.77(13) . . ?
O1 C6 C7 111.58(14) . . ?
O1 C5 C4 110.95(15) . . ?

_refine_diff_density_max         0.526
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.048


# start Validation Reply Form
_vrf_PLAT430_shelx               
;
PROBLEM: Short Inter D...A Contact O2 ..O2 . 1.50 Ang.
RESPONSE: It is a water molecule shared between two positions
;
_vrf_PLAT431_shelx               
;
PROBLEM: Short Inter HL..A Contact F3 ..O2 . 2.36 Ang.
RESPONSE: This is a H-bond contact. The hydrogen atom was not clearly found in the deltaF map
;
# end Validation Reply Form

#===END

####################################################################### 
# 
# 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 1584770'
_audit_update_record             
;
2017-11-23 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H26 Br2 N6 O2'
_chemical_formula_weight         470.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.0275(6)
_cell_length_b                   13.5630(9)
_cell_length_c                   11.9342(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.374(8)
_cell_angle_gamma                90
_cell_volume                     945.09(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    1759
_cell_measurement_theta_min      5.0270
_cell_measurement_theta_max      72.1900

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'deep pink'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_F_000             476
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    5.613
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.54538
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 8.1241
_diffrn_reflns_number            5937
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.027
_diffrn_reflns_theta_max         72.165
_diffrn_reflns_theta_full        67.500
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             1770
_reflns_number_gt                1525
_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.9'
_computing_publication_material  'PARST93 (Nardelli, 1993)'
_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)+(0.0387P)²+2.2688P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1770
_refine_ls_number_parameters     113
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_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
Br01 Br -0.16894(7) 0.26541(3) -0.08168(3) 0.02148(16) Uani 1 1 d . . . . .
O002 O 0.3426(5) 0.0383(2) 0.0979(2) 0.0257(7) Uani 1 1 d . . . . .
N003 N -0.1982(6) 0.5228(2) 0.0299(3) 0.0237(7) Uani 1 1 d . . . . .
N004 N -0.0266(6) 0.4832(2) 0.1081(3) 0.0225(7) Uani 1 1 d . . . . .
N005 N 0.2465(6) 0.2387(2) 0.1471(3) 0.0176(7) Uani 1 1 d . . . . .
C006 C 0.3607(8) 0.4196(3) 0.1664(4) 0.0268(9) Uani 1 1 d . . . . .
H00A H 0.4172 0.4693 0.2251 0.032 Uiso 1 1 calc R U . . .
H00B H 0.4845 0.4031 0.1310 0.032 Uiso 1 1 calc R U . . .
C007 C 0.2952(7) 0.3279(3) 0.2243(3) 0.0234(9) Uani 1 1 d . . . . .
H00C H 0.4187 0.3121 0.2912 0.028 Uiso 1 1 calc R U . . .
H00D H 0.1604 0.3425 0.2519 0.028 Uiso 1 1 calc R U . . .
C008 C 0.1905(7) 0.1527(3) 0.2153(3) 0.0222(8) Uani 1 1 d . . . . .
H00E H 0.3173 0.1407 0.2819 0.027 Uiso 1 1 calc R U . . .
H00F H 0.0561 0.1680 0.2430 0.027 Uiso 1 1 calc R U . . .
C009 C 0.3859(8) 0.1175(3) 0.0278(3) 0.0230(9) Uani 1 1 d . . . . .
H00G H 0.2520 0.1279 -0.0356 0.028 Uiso 1 1 calc R U . . .
H00H H 0.5127 0.0999 -0.0050 0.028 Uiso 1 1 calc R U . . .
C010 C 0.1665(7) 0.4623(3) 0.0759(3) 0.0206(8) Uani 1 1 d . . . . .
C011 C 0.4427(7) 0.2121(3) 0.0961(4) 0.0218(8) Uani 1 1 d . . . . .
H01A H 0.5810 0.2034 0.1574 0.026 Uiso 1 1 calc R U . . .
H01B H 0.4690 0.2646 0.0458 0.026 Uiso 1 1 calc R U . . .
C012 C 0.1461(7) 0.0617(3) 0.1405(4) 0.0242(9) Uani 1 1 d . . . . .
H01C H 0.1111 0.0067 0.1851 0.029 Uiso 1 1 calc R U . . .
H01D H 0.0148 0.0728 0.0758 0.029 Uiso 1 1 calc R U . . .
H1 H 0.127(9) 0.250(4) 0.085(5) 0.034(14) 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
O002 C009 1.425(5) . ?
O002 C012 1.436(5) . ?
N003 N004 1.323(5) . ?
N003 C010 1.338(5) 3_565 ?
N004 C010 1.343(5) . ?
N005 C011 1.502(5) . ?
N005 C007 1.505(5) . ?
N005 C008 1.509(5) . ?
C006 C010 1.498(6) . ?
C006 C007 1.523(6) . ?
C008 C012 1.508(6) . ?
C009 C011 1.513(5) . ?
C010 N003 1.338(5) 3_565 ?

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
C009 O002 C012 109.2(3) . . ?
N004 N003 C010 117.2(3) . 3_565 ?
N003 N004 C010 117.8(3) . . ?
C011 N005 C007 112.9(3) . . ?
C011 N005 C008 109.7(3) . . ?
C007 N005 C008 109.0(3) . . ?
C010 C006 C007 113.5(4) . . ?
N005 C007 C006 114.3(3) . . ?
C012 C008 N005 110.1(3) . . ?
O002 C009 C011 111.9(3) . . ?
N003 C010 N004 125.1(4) 3_565 . ?
N003 C010 C006 118.0(4) 3_565 . ?
N004 C010 C006 116.9(4) . . ?
N005 C011 C009 109.1(3) . . ?
O002 C012 C008 110.5(3) . . ?

_refine_diff_density_max         0.606
_refine_diff_density_min         -0.960
_refine_diff_density_rms         0.126


# start Validation Reply Form
_vrf_PLAT934_shelx               
;
PROBLEM: Number of (Iobs-Icalc)/SigmaW > 10 Outliers .... 2 Check
RESPONSE: The two outliers are high theta reflections (65.81 and 64.39 deg) 
featuring low observed intensity.
;
# end Validation Reply Form
#===END
####################################################################### 
# 
# 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 1584769'
_audit_update_record             
;
2017-11-23 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H26 Cl2 N6 O2'
_chemical_formula_weight         381.31

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.8409(2)
_cell_length_b                   13.9837(7)
_cell_length_c                   11.5093(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 103.017(4)
_cell_angle_gamma                90.000(5)
_cell_volume                     915.89(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293
_cell_measurement_reflns_used    1759
_cell_measurement_theta_min      5.0270
_cell_measurement_theta_max      72.1900

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'deep pink'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    3.363
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.54538
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 8.1241
_diffrn_reflns_number            5948
_diffrn_reflns_av_unetI/netI     0.0795
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.056
_diffrn_reflns_theta_max         72.141
_diffrn_reflns_theta_full        67.680
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1741
_reflns_number_gt                1189
_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.9'
_computing_publication_material  'PARST93 (Nardelli, 1993)'
_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)+(0.0242P)²+0.2036P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1741
_refine_ls_number_parameters     113
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0816
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.145
_refine_ls_shift/su_max          0.002
_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
Cl01 Cl -0.08803(13) 0.27662(6) 1.07484(6) 0.0246(2) Uani 1 1 d . . . . .
O002 O 0.2215(4) 0.04088(16) 0.90308(18) 0.0270(6) Uani 1 1 d . . . . .
N003 N -0.1187(5) 0.4806(2) 0.8876(2) 0.0245(6) Uani 1 1 d . . . . .
N004 N 0.1124(4) 0.23964(18) 0.85544(19) 0.0160(6) Uani 1 1 d . . . . .
N005 N -0.2318(5) 0.5234(2) 0.9608(2) 0.0256(7) Uani 1 1 d . . . . .
C006 C 0.1036(6) 0.3261(2) 0.7783(3) 0.0237(7) Uani 1 1 d . . . . .
H00A H -0.0596 0.3429 0.7463 0.028 Uiso 1 1 calc R U . . .
H00B H 0.1726 0.3103 0.7116 0.028 Uiso 1 1 calc R U . . .
C007 C 0.1079(6) 0.4594(2) 0.9281(3) 0.0210(7) Uani 1 1 d . . . . .
C008 C -0.0149(6) 0.0713(2) 0.8594(3) 0.0251(8) Uani 1 1 d . . . . .
H00C H -0.0864 0.0842 0.9261 0.030 Uiso 1 1 calc R U . . .
H00D H -0.1036 0.0206 0.8121 0.030 Uiso 1 1 calc R U . . .
C009 C 0.2297(6) 0.4126(2) 0.8418(3) 0.0274(8) Uani 1 1 d . . . . .
H00E H 0.3854 0.3931 0.8844 0.033 Uiso 1 1 calc R U . . .
H00F H 0.2486 0.4593 0.7824 0.033 Uiso 1 1 calc R U . . .
C010 C 0.3496(6) 0.1148(2) 0.9760(3) 0.0248(8) Uani 1 1 d . . . . .
H01A H 0.5086 0.0931 1.0090 0.030 Uiso 1 1 calc R U . . .
H01B H 0.2759 0.1280 1.0419 0.030 Uiso 1 1 calc R U . . .
C011 C -0.0261(5) 0.1601(2) 0.7842(3) 0.0214(7) Uani 1 1 d . . . . .
H01C H 0.0372 0.1465 0.7149 0.026 Uiso 1 1 calc R U . . .
H01D H -0.1885 0.1798 0.7565 0.026 Uiso 1 1 calc R U . . .
C012 C 0.3577(5) 0.2053(2) 0.9062(3) 0.0240(8) Uani 1 1 d . . . . .
H01E H 0.4449 0.2540 0.9579 0.029 Uiso 1 1 calc R U . . .
H01F H 0.4372 0.1934 0.8422 0.029 Uiso 1 1 calc R U . . .
H1 H 0.040(5) 0.251(2) 0.925(3) 0.023(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
O002 C008 1.424(4) . ?
O002 C010 1.432(4) . ?
N003 N005 1.325(4) . ?
N003 C007 1.334(4) . ?
N004 C006 1.494(4) . ?
N004 C012 1.499(4) . ?
N004 C011 1.505(4) . ?
N005 C007 1.341(4) 3_567 ?
C006 C009 1.514(5) . ?
C007 N005 1.341(4) 3_567 ?
C007 C009 1.496(4) . ?
C008 C011 1.506(4) . ?
C010 C012 1.505(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
C008 O002 C010 109.1(2) . . ?
N005 N003 C007 118.5(3) . . ?
C006 N004 C012 113.1(2) . . ?
C006 N004 C011 109.4(2) . . ?
C012 N004 C011 109.0(2) . . ?
N003 N005 C007 116.6(3) . 3_567 ?
N004 C006 C009 114.3(2) . . ?
N003 C007 N005 124.9(3) . 3_567 ?
N003 C007 C009 116.6(3) . . ?
N005 C007 C009 118.4(3) 3_567 . ?
O002 C008 C011 111.2(3) . . ?
C007 C009 C006 114.6(3) . . ?
O002 C010 C012 111.7(2) . . ?
N004 C011 C008 110.3(2) . . ?
N004 C012 C010 109.5(2) . . ?

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.285
_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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1584771'
_audit_update_record             
;
2017-11-23 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H20 N6 O2'
_chemical_formula_weight         280.34

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.2753(4)
_cell_length_b                   13.9813(8)
_cell_length_c                   7.4837(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.110(5)
_cell_angle_gamma                90
_cell_volume                     651.55(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    521
_cell_measurement_theta_min      5.9537
_cell_measurement_theta_max      55.2997

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'deep pink'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.840
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.51787
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 8.1241
_diffrn_reflns_number            1652
_diffrn_reflns_av_unetI/netI     0.0788
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         6.331
_diffrn_reflns_theta_max         55.369
_diffrn_reflns_theta_full        55.369
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             822
_reflns_number_gt                565
_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.9'
_computing_publication_material  'PARST93 (Nardelli, 1993)'
_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)+(0.1384P)²+5.0944P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         822
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1958
_refine_ls_wR_factor_gt          0.1367
_refine_ls_goodness_of_fit_ref   0.658
_refine_ls_restrained_S_all      0.658
_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
N1 N 0.4193(6) 0.4878(3) -0.1774(5) 0.0268(11) Uani 1 1 d . . . . .
N2 N 0.2938(6) 0.4721(3) -0.0495(5) 0.0276(11) Uani 1 1 d . . . . .
C1 C 0.3780(7) 0.4850(3) 0.1233(6) 0.0208(12) Uani 1 1 d . . . . .
C2 C 0.2330(8) 0.4685(3) 0.2643(6) 0.0253(13) Uani 1 1 d . . . . .
H2A H 0.2984 0.4954 0.3775 0.030 Uiso 1 1 calc R U . . .
H2B H 0.0981 0.5015 0.2301 0.030 Uiso 1 1 calc R U . . .
N3 N 0.1904(6) 0.3670(3) 0.2895(5) 0.0218(10) Uani 1 1 d . . . . .
C4 C 0.0136(8) 0.3548(3) 0.3988(7) 0.0248(12) Uani 1 1 d . . . . .
H4A H -0.1135 0.3873 0.3415 0.030 Uiso 1 1 calc R U . . .
H4B H 0.0525 0.3832 0.5166 0.030 Uiso 1 1 calc R U . . .
C5 C -0.0339(8) 0.2505(4) 0.4192(7) 0.0287(13) Uani 1 1 d . . . . .
H5A H -0.1517 0.2432 0.4907 0.034 Uiso 1 1 calc R U . . .
H5B H -0.0776 0.2229 0.3015 0.034 Uiso 1 1 calc R U . . .
O1 O 0.1504(5) 0.2009(2) 0.5042(4) 0.0272(9) Uani 1 1 d . . . . .
C6 C 0.3262(8) 0.2119(4) 0.4023(7) 0.0280(13) Uani 1 1 d . . . . .
H6A H 0.2909 0.1820 0.2854 0.034 Uiso 1 1 calc R U . . .
H6B H 0.4512 0.1797 0.4638 0.034 Uiso 1 1 calc R U . . .
C7 C 0.3792(7) 0.3165(3) 0.3766(6) 0.0242(12) Uani 1 1 d . . . . .
H7A H 0.4260 0.3455 0.4926 0.029 Uiso 1 1 calc R U . . .
H7B H 0.4955 0.3217 0.3030 0.029 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
N1 N2 1.331(5) . ?
N1 C1 1.341(6) 3_665 ?
N2 C1 1.347(6) . ?
C1 N1 1.341(6) 3_665 ?
C1 C2 1.494(6) . ?
C2 N3 1.460(6) . ?
N3 C7 1.461(6) . ?
N3 C4 1.468(6) . ?
C4 C5 1.500(7) . ?
C5 O1 1.429(6) . ?
O1 C6 1.425(6) . ?
C6 C7 1.517(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 117.0(4) . 3_665 ?
N1 N2 C1 118.1(4) . . ?
N1 C1 N2 124.9(4) 3_665 . ?
N1 C1 C2 117.9(4) 3_665 . ?
N2 C1 C2 117.2(4) . . ?
N3 C2 C1 112.2(4) . . ?
C2 N3 C7 112.1(4) . . ?
C2 N3 C4 110.3(4) . . ?
C7 N3 C4 108.8(4) . . ?
N3 C4 C5 110.0(4) . . ?
O1 C5 C4 110.9(4) . . ?
C5 O1 C6 110.3(3) . . ?
O1 C6 C7 111.6(4) . . ?
N3 C7 C6 110.1(4) . . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.058


# start Validation Reply Form
_vrf_THETM01_shelx               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Due to very low intensity of reflections data were collected
only up to theta=55.4\% (0.94 A resolution)
;
# end Validation Reply Form
#===END
####################################################################### 
# 
# 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 1584772'
_audit_update_record             
;
2017-11-23 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H24 N6 O2'
_chemical_formula_weight         308.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.6821(6)
_cell_length_b                   6.8313(2)
_cell_length_c                   10.7321(6)
_cell_angle_alpha                90
_cell_angle_beta                 117.200(7)
_cell_angle_gamma                90
_cell_volume                     761.75(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    2519
_cell_measurement_theta_min      7.9680
_cell_measurement_theta_max      77.6420

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'deep pink'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             332
_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    0.767
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.86406
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32e (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scan'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_reflns_number            3813
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.255
_diffrn_reflns_theta_max         77.416
_diffrn_reflns_theta_full        67.500
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             1541
_reflns_number_gt                1428
_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       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.9'
_computing_publication_material  'PARST93 (Nardelli, 1993)'
_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)+(0.0513P)²+0.2224P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1541
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.1019
_refine_ls_wR_factor_gt          0.1002
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.142
_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 0.93344(7) 0.70018(12) 0.32748(8) 0.0214(2) Uani 1 1 d . . . . .
N11 N 0.58069(8) -0.03442(13) 0.44313(9) 0.0169(2) Uani 1 1 d . . . . .
N1 N 0.73468(8) 0.43680(13) 0.31125(9) 0.0154(2) Uani 1 1 d . . . . .
N10 N 0.54050(8) -0.18402(13) 0.49171(9) 0.0174(2) Uani 1 1 d . . . . .
C9 C 0.53908(10) 0.14482(15) 0.45272(10) 0.0150(2) Uani 1 1 d . . . . .
C6 C 0.84122(10) 0.37322(16) 0.28339(11) 0.0171(3) Uani 1 1 d . . . . .
H6A H 0.8117 0.2689 0.2144 0.021 Uiso 1 1 calc R U . . .
H6B H 0.9107 0.3223 0.3689 0.021 Uiso 1 1 calc R U . . .
C5 C 0.89056(10) 0.54223(16) 0.22969(12) 0.0193(3) Uani 1 1 d . . . . .
H5A H 0.9612 0.4973 0.2131 0.023 Uiso 1 1 calc R U . . .
H5B H 0.8224 0.5879 0.1413 0.023 Uiso 1 1 calc R U . . .
C2 C 0.78017(10) 0.60131(16) 0.41058(12) 0.0184(3) Uani 1 1 d . . . . .
H2A H 0.8483 0.5569 0.4994 0.022 Uiso 1 1 calc R U . . .
H2B H 0.7101 0.6498 0.4268 0.022 Uiso 1 1 calc R U . . .
C7 C 0.69518(10) 0.27010(16) 0.36849(11) 0.0167(3) Uani 1 1 d . . . . .
H7A H 0.7674 0.2292 0.4554 0.020 Uiso 1 1 calc R U . . .
H7B H 0.6725 0.1616 0.3032 0.020 Uiso 1 1 calc R U . . .
C8 C 0.58105(11) 0.31626(16) 0.39624(12) 0.0188(3) Uani 1 1 d . . . . .
H8A H 0.6042 0.4234 0.4627 0.023 Uiso 1 1 calc R U . . .
H8B H 0.5093 0.3592 0.3096 0.023 Uiso 1 1 calc R U . . .
C3 C 0.82996(11) 0.76452(17) 0.35283(13) 0.0216(3) Uani 1 1 d . . . . .
H3A H 0.7605 0.8121 0.2660 0.026 Uiso 1 1 calc R U . . .
H3B H 0.8590 0.8723 0.4190 0.026 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 C3 1.4245(12) . ?
O4 C5 1.4269(13) . ?
N11 N10 1.3268(12) . ?
N11 C9 1.3386(14) . ?
N1 C7 1.4650(13) . ?
N1 C2 1.4711(14) . ?
N1 C6 1.4721(13) . ?
N10 C9 1.3410(13) 3_656 ?
C9 N10 1.3411(13) 3_656 ?
C9 C8 1.5003(14) . ?
C6 C5 1.5169(14) . ?
C2 C3 1.5150(14) . ?
C7 C8 1.5260(14) . ?

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
C3 O4 C5 109.30(8) . . ?
N10 N11 C9 117.92(8) . . ?
C7 N1 C2 111.63(8) . . ?
C7 N1 C6 108.27(8) . . ?
C2 N1 C6 108.28(8) . . ?
N11 N10 C9 117.56(9) . 3_656 ?
N11 C9 N10 124.52(9) . 3_656 ?
N11 C9 C8 119.06(9) . . ?
N10 C9 C8 116.41(9) 3_656 . ?
N1 C6 C5 110.85(8) . . ?
O4 C5 C6 111.27(8) . . ?
N1 C2 C3 110.17(8) . . ?
N1 C7 C8 113.08(9) . . ?
C9 C8 C7 113.18(9) . . ?
O4 C3 C2 111.66(9) . . ?

_refine_diff_density_max         0.348
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.052

