# Electronic Supplementary Material (ESI) for ChemComm.
# 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_pbar1_768971_a
_database_code_depnum_ccdc_archive 'CCDC 1852341'
_audit_update_record             
;
2018-08-03 deposited with the CCDC.
2018-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H24 Cl5 N4 Np O2'
_chemical_formula_weight         622.56

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'
Cl Cl 0.1484 0.1585 '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'
Np Np -11.4937 4.1493 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   7.4041(10)
_cell_length_b                   10.4454(11)
_cell_length_c                   12.3566(16)
_cell_angle_alpha                76.494(10)
_cell_angle_beta                 89.313(9)
_cell_angle_gamma                71.795(7)
_cell_volume                     880.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    513
_cell_measurement_theta_min      2
_cell_measurement_theta_max      25

_exptl_crystal_description       blocky
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.347
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    6.662
_shelx_estimated_absorpt_T_min   0.108
_shelx_estimated_absorpt_T_max   0.555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6531
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'Psi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53635
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.115
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4028
_reflns_number_gt                4012
_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       'APEX3 (Bruker, Madison, WI)'
_computing_cell_refinement       'APEX3 (Bruker, Madison, WI)'
_computing_data_reduction        'APEX3 (Bruker, Madison, WI)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Crystalmaker X'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+0.6367P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0134(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4028
_refine_ls_number_parameters     206
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0103
_refine_ls_R_factor_gt           0.0102
_refine_ls_wR_factor_ref         0.0250
_refine_ls_wR_factor_gt          0.0247
_refine_ls_goodness_of_fit_ref   1.324
_refine_ls_restrained_S_all      1.324
_refine_ls_shift/su_max          0.005
_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
Np1 Np 0.35892(2) 0.73588(2) 0.67688(2) 0.00472(3) Uani 1 1 d . . . . .
Cl1 Cl 0.43039(6) 0.46029(4) 0.77650(3) 0.01191(8) Uani 1 1 d . . . . .
Cl2 Cl 0.38644(6) 0.78145(4) 0.88459(3) 0.01048(8) Uani 1 1 d . . . . .
Cl3 Cl 0.31211(6) 0.68466(4) 0.47011(3) 0.00855(7) Uani 1 1 d . . . . .
Cl4 Cl 0.24134(6) 1.01600(4) 0.57343(3) 0.00969(7) Uani 1 1 d . . . . .
Cl5 Cl -0.19813(6) 0.82796(4) 0.04419(3) 0.01032(8) Uani 1 1 d . . . . .
O1 O 0.61077(17) 0.71535(12) 0.65729(10) 0.0097(2) Uani 1 1 d . . . . .
O2 O 0.10504(17) 0.75310(12) 0.69802(10) 0.0085(2) Uani 1 1 d . . . . .
N1 N 0.3831(2) 0.88906(16) 0.13176(12) 0.0098(3) Uani 1 1 d D . . . .
H1B H 0.354(3) 0.9677(18) 0.0797(16) 0.012 Uiso 1 1 d D U . . .
H1C H 0.467(3) 0.825(2) 0.1060(18) 0.012 Uiso 1 1 d D U . . .
N2 N 0.0471(2) 0.60939(15) 0.92506(12) 0.0114(3) Uani 1 1 d D . . . .
H2B H 0.107(3) 0.643(2) 0.8670(16) 0.014 Uiso 1 1 d D U . . .
H2C H -0.022(3) 0.6837(19) 0.9494(18) 0.014 Uiso 1 1 d D U . . .
N3 N 0.9263(2) 0.62327(15) 0.54276(12) 0.0100(3) Uani 1 1 d D . . . .
H3B H 1.018(3) 0.663(2) 0.5338(18) 0.012 Uiso 1 1 d D U . . .
H3C H 0.832(3) 0.672(2) 0.5762(17) 0.012 Uiso 1 1 d D U . . .
N4 N 0.1506(2) 0.98084(15) 0.30456(12) 0.0084(3) Uani 1 1 d D . . . .
H4B H 0.069(3) 1.0510(19) 0.3259(18) 0.010 Uiso 1 1 d D U . . .
H4C H 0.178(3) 0.9048(18) 0.3601(15) 0.010 Uiso 1 1 d D U . . .
C1 C 0.2100(2) 0.84654(18) 0.15915(15) 0.0115(3) Uani 1 1 d . . . . .
H1A H 0.246060 0.755993 0.214682 0.014 Uiso 1 1 calc R U . . .
H1AB H 0.153371 0.835616 0.091064 0.014 Uiso 1 1 calc R U . . .
C2 C -0.0846(3) 0.54272(18) 0.88798(14) 0.0127(3) Uani 1 1 d . . . . .
H2A H -0.010736 0.464243 0.856908 0.015 Uiso 1 1 calc R U . . .
H2AB H -0.177200 0.610988 0.828549 0.015 Uiso 1 1 calc R U . . .
C3 C 1.1535(2) 0.38430(18) 0.56486(14) 0.0111(3) Uani 1 1 d . . . . .
H3A H 1.265986 0.416504 0.551171 0.013 Uiso 1 1 calc R U . . .
H3AB H 1.195896 0.290501 0.615889 0.013 Uiso 1 1 calc R U . . .
C4 C 0.1900(3) 0.50963(18) 1.01478(15) 0.0129(3) Uani 1 1 d . . . . .
H4A H 0.273888 0.556525 1.039123 0.015 Uiso 1 1 calc R U . . .
H4AB H 0.270114 0.430791 0.986220 0.015 Uiso 1 1 calc R U . . .
C5 C 0.0652(2) 0.95510(18) 0.20574(14) 0.0100(3) Uani 1 1 d . . . . .
H5A H 0.019261 1.042857 0.147243 0.012 Uiso 1 1 calc R U . . .
H5AB H -0.045398 0.923212 0.228031 0.012 Uiso 1 1 calc R U . . .
C6 C 0.3264(2) 1.01954(18) 0.27797(14) 0.0104(3) Uani 1 1 d . . . . .
H6A H 0.383247 1.029755 0.346314 0.012 Uiso 1 1 calc R U . . .
H6BC H 0.293172 1.109948 0.222369 0.012 Uiso 1 1 calc R U . . .
C7 C 0.4700(2) 0.91006(18) 0.23215(14) 0.0098(3) Uani 1 1 d . . . . .
H7B H 0.583150 0.939492 0.211625 0.012 Uiso 1 1 calc R U . . .
H7BC H 0.511940 0.821504 0.290005 0.012 Uiso 1 1 calc R U . . .
C8 C 1.0068(3) 0.48273(18) 0.61938(14) 0.0112(3) Uani 1 1 d . . . . .
H8A H 0.902227 0.443877 0.642048 0.013 Uiso 1 1 calc R U . . .
H8AB H 1.066765 0.491122 0.687444 0.013 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
Np1 O1 1.8290(12) . ?
Np1 O2 1.8528(12) . ?
Np1 Cl1 2.7369(5) . ?
Np1 Cl2 2.7385(5) . ?
Np1 Cl4 2.7643(5) . ?
Np1 Cl3 2.7768(5) . ?
N1 C1 1.493(2) . ?
N1 C7 1.495(2) . ?
N1 H1B 0.884(15) . ?
N1 H1C 0.877(16) . ?
N2 C2 1.493(2) . ?
N2 C4 1.494(2) . ?
N2 H2B 0.897(16) . ?
N2 H2C 0.901(16) . ?
N3 C3 1.490(2) 2_766 ?
N3 C8 1.491(2) . ?
N3 H3B 0.899(16) . ?
N3 H3C 0.889(16) . ?
N4 C6 1.491(2) . ?
N4 C5 1.497(2) . ?
N4 H4B 0.884(15) . ?
N4 H4C 0.890(15) . ?
C1 C5 1.516(2) . ?
C1 H1A 0.9900 . ?
C1 H1AB 0.9900 . ?
C2 C4 1.513(2) 2_567 ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C8 1.516(2) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C6 C7 1.512(2) . ?
C6 H6A 0.9900 . ?
C6 H6BC 0.9900 . ?
C7 H7B 0.9900 . ?
C7 H7BC 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Np1 O2 178.91(5) . . ?
O1 Np1 Cl1 93.20(4) . . ?
O2 Np1 Cl1 85.71(4) . . ?
O1 Np1 Cl2 92.04(4) . . ?
O2 Np1 Cl2 87.92(4) . . ?
Cl1 Np1 Cl2 88.293(16) . . ?
O1 Np1 Cl4 93.47(4) . . ?
O2 Np1 Cl4 87.62(4) . . ?
Cl1 Np1 Cl4 173.103(13) . . ?
Cl2 Np1 Cl4 93.233(17) . . ?
O1 Np1 Cl3 91.12(4) . . ?
O2 Np1 Cl3 88.89(4) . . ?
Cl1 Np1 Cl3 90.170(16) . . ?
Cl2 Np1 Cl3 176.554(12) . . ?
Cl4 Np1 Cl3 87.935(16) . . ?
C1 N1 C7 111.20(13) . . ?
C1 N1 H1B 110.5(15) . . ?
C7 N1 H1B 108.1(14) . . ?
C1 N1 H1C 109.6(15) . . ?
C7 N1 H1C 109.5(15) . . ?
H1B N1 H1C 108(2) . . ?
C2 N2 C4 111.38(13) . . ?
C2 N2 H2B 110.3(14) . . ?
C4 N2 H2B 109.9(15) . . ?
C2 N2 H2C 109.1(15) . . ?
C4 N2 H2C 110.3(14) . . ?
H2B N2 H2C 106(2) . . ?
C3 N3 C8 111.55(13) 2_766 . ?
C3 N3 H3B 112.9(14) 2_766 . ?
C8 N3 H3B 107.9(14) . . ?
C3 N3 H3C 108.2(14) 2_766 . ?
C8 N3 H3C 107.3(14) . . ?
H3B N3 H3C 109(2) . . ?
C6 N4 C5 111.86(13) . . ?
C6 N4 H4B 106.7(14) . . ?
C5 N4 H4B 109.9(14) . . ?
C6 N4 H4C 109.7(14) . . ?
C5 N4 H4C 109.1(14) . . ?
H4B N4 H4C 109(2) . . ?
N1 C1 C5 110.07(14) . . ?
N1 C1 H1A 109.6 . . ?
C5 C1 H1A 109.6 . . ?
N1 C1 H1AB 109.6 . . ?
C5 C1 H1AB 109.6 . . ?
H1A C1 H1AB 108.2 . . ?
N2 C2 C4 110.22(14) . 2_567 ?
N2 C2 H2A 109.6 . . ?
C4 C2 H2A 109.6 2_567 . ?
N2 C2 H2AB 109.6 . . ?
C4 C2 H2AB 109.6 2_567 . ?
H2A C2 H2AB 108.1 . . ?
N3 C3 C8 111.19(14) 2_766 . ?
N3 C3 H3A 109.4 2_766 . ?
C8 C3 H3A 109.4 . . ?
N3 C3 H3AB 109.4 2_766 . ?
C8 C3 H3AB 109.4 . . ?
H3A C3 H3AB 108.0 . . ?
N2 C4 C2 108.59(14) . 2_567 ?
N2 C4 H4A 110.0 . . ?
C2 C4 H4A 110.0 2_567 . ?
N2 C4 H4AB 110.0 . . ?
C2 C4 H4AB 110.0 2_567 . ?
H4A C4 H4AB 108.4 . . ?
N4 C5 C1 110.97(14) . . ?
N4 C5 H5A 109.4 . . ?
C1 C5 H5A 109.4 . . ?
N4 C5 H5AB 109.4 . . ?
C1 C5 H5AB 109.4 . . ?
H5A C5 H5AB 108.0 . . ?
N4 C6 C7 110.72(13) . . ?
N4 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
N4 C6 H6BC 109.5 . . ?
C7 C6 H6BC 109.5 . . ?
H6A C6 H6BC 108.1 . . ?
N1 C7 C6 110.05(14) . . ?
N1 C7 H7B 109.7 . . ?
C6 C7 H7B 109.7 . . ?
N1 C7 H7BC 109.7 . . ?
C6 C7 H7BC 109.7 . . ?
H7B C7 H7BC 108.2 . . ?
N3 C8 C3 111.81(14) . . ?
N3 C8 H8A 109.3 . . ?
C3 C8 H8A 109.3 . . ?
N3 C8 H8AB 109.3 . . ?
C3 C8 H8AB 109.3 . . ?
H8A C8 H8AB 107.9 . . ?

_refine_diff_density_max         0.476
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.099

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

data_MBTF_Np_UMON_59_a
_database_code_depnum_ccdc_archive 'CCDC 1852343'
_audit_update_record             
;
2018-06-29 deposited with the CCDC.
2018-08-17 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT971_MBTF_Np_UMON_59_a   
;
PROBLEM: Check Calcd Resid. Dens.  0.65A   From Np1             3.71 eA-3
RESPONSE: We attribute this residual density to an artifact of the presence of the heavy atom Np1.
;
_vrf_PLAT975_MBTF_Np_UMON_59_a   
;
PROBLEM: Check Calcd Resid. Dens.  0.97A   From O2              2.29 eA-3
RESPONSE: We attribute this residual density to an artifact of the presence and proximity of the heavy atom, Np1.
;
# Added during the CSD deposition process: Friday 29 June 2018 01:55 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H6 N Np O6'
_chemical_formula_weight         401.10

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'
Np Np -11.4937 4.1493 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           59
_space_group_name_H-M_alt        'P m m n'
_space_group_name_Hall           '-P 2ab 2a'

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

_cell_length_a                   8.2246(8)
_cell_length_b                   9.7709(8)
_cell_length_c                   4.5380(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     364.68(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2110
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      23.22

_exptl_crystal_description       plate
_exptl_crystal_colour            green-blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.653
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    14.239
_shelx_estimated_absorpt_T_min   0.280
_shelx_estimated_absorpt_T_max   0.600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0476
_exptl_absorpt_correction_T_max  0.1044
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21137
_diffrn_reflns_av_unetI/netI     0.0118
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.238
_diffrn_reflns_theta_max         33.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             772
_reflns_number_gt                755
_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       'APEX3 (Bruker, Madison, WI)'
_computing_cell_refinement       'APEX3 (Bruker, Madison, WI)'
_computing_data_reduction        'APEX3 (Bruker, Madison, WI)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'CrystalMaker X'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0103P)²+3.2347P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         772
_refine_ls_number_parameters     39
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0193
_refine_ls_R_factor_gt           0.0187
_refine_ls_wR_factor_ref         0.0468
_refine_ls_wR_factor_gt          0.0466
_refine_ls_goodness_of_fit_ref   1.297
_refine_ls_restrained_S_all      1.277
_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
Np1 Np 0.750000 0.250000 -0.01660(5) 0.00486(7) Uani 1 4 d S T P . .
O1 O 0.750000 0.3823(4) 0.5023(8) 0.0189(8) Uani 1 2 d S T P . .
O1' O 0.5286(5) 0.250000 -0.0133(9) 0.0251(10) Uani 1 2 d S T P . .
N1 N 0.750000 0.750000 0.3545(13) 0.0102(10) Uani 1 4 d S T P . .
H1A H 0.839589 0.750000 0.236845 0.012 Uiso 0.5 2 calc R U P . .
H1B H 0.660411 0.750000 0.236845 0.012 Uiso 0.5 2 calc R U P . .
C1 C 0.750000 0.4962(5) 0.3697(12) 0.0199(11) Uani 1 2 d S T P . .
C2 C 0.750000 0.6262(5) 0.5403(11) 0.0138(8) Uani 1 2 d S T P . .
H2A H 0.652817 0.628083 0.668930 0.017 Uiso 0.5 1 calc R U P . .
H2B H 0.847183 0.628083 0.668930 0.017 Uiso 0.5 1 calc R U P . .
O2 O 0.750000 0.5014(4) 0.0929(10) 0.0390(15) Uani 1 2 d S T P . .


_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
Np1 O1' 1.821(4) . ?
Np1 O1' 1.821(4) 2_655 ?
Np1 O2 2.506(4) . ?
Np1 O2 2.506(4) 2_655 ?
Np1 O1 2.538(3) 2_654 ?
Np1 O1 2.538(3) 1_554 ?
Np1 O1 2.686(4) 2_655 ?
Np1 O1 2.686(4) . ?
Np1 C1 2.977(5) . ?
Np1 C1 2.977(5) 2_655 ?
O1 C1 1.265(6) . ?
N1 C2 1.474(6) 2_665 ?
N1 C2 1.474(6) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
C1 O2 1.257(7) . ?
C1 C2 1.487(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1' Np1 O1' 179.1(3) . 2_655 ?
O1' Np1 O2 89.91(3) . . ?
O1' Np1 O2 89.91(3) 2_655 . ?
O1' Np1 O2 89.91(3) . 2_655 ?
O1' Np1 O2 89.91(3) 2_655 2_655 ?
O2 Np1 O2 157.1(2) . 2_655 ?
O1' Np1 O1 90.41(11) . 2_654 ?
O1' Np1 O1 90.41(11) 2_655 2_654 ?
O2 Np1 O1 132.07(13) . 2_654 ?
O2 Np1 O1 70.80(13) 2_655 2_654 ?
O1' Np1 O1 90.41(11) . 1_554 ?
O1' Np1 O1 90.41(11) 2_655 1_554 ?
O2 Np1 O1 70.80(13) . 1_554 ?
O2 Np1 O1 132.07(13) 2_655 1_554 ?
O1 Np1 O1 61.27(16) 2_654 1_554 ?
O1' Np1 O1 89.58(11) . 2_655 ?
O1' Np1 O1 89.58(11) 2_655 2_655 ?
O2 Np1 O1 107.34(13) . 2_655 ?
O2 Np1 O1 49.79(13) 2_655 2_655 ?
O1 Np1 O1 120.59(14) 2_654 2_655 ?
O1 Np1 O1 178.14(8) 1_554 2_655 ?
O1' Np1 O1 89.58(11) . . ?
O1' Np1 O1 89.58(11) 2_655 . ?
O2 Np1 O1 49.79(13) . . ?
O2 Np1 O1 107.34(13) 2_655 . ?
O1 Np1 O1 178.14(8) 2_654 . ?
O1 Np1 O1 120.59(14) 1_554 . ?
O1 Np1 O1 57.55(15) 2_655 . ?
O1' Np1 C1 89.72(7) . . ?
O1' Np1 C1 89.72(7) 2_655 . ?
O2 Np1 C1 24.64(14) . . ?
O2 Np1 C1 132.48(15) 2_655 . ?
O1 Np1 C1 156.72(13) 2_654 . ?
O1 Np1 C1 95.44(13) 1_554 . ?
O1 Np1 C1 82.69(13) 2_655 . ?
O1 Np1 C1 25.15(12) . . ?
O1' Np1 C1 89.72(7) . 2_655 ?
O1' Np1 C1 89.72(7) 2_655 2_655 ?
O2 Np1 C1 132.48(15) . 2_655 ?
O2 Np1 C1 24.64(14) 2_655 2_655 ?
O1 Np1 C1 95.44(13) 2_654 2_655 ?
O1 Np1 C1 156.71(13) 1_554 2_655 ?
O1 Np1 C1 25.15(12) 2_655 2_655 ?
O1 Np1 C1 82.70(13) . 2_655 ?
C1 Np1 C1 107.8(2) . 2_655 ?
C1 O1 Np1 149.0(3) . 1_556 ?
C1 O1 Np1 90.4(3) . . ?
Np1 O1 Np1 120.59(14) 1_556 . ?
C2 N1 C2 110.2(5) 2_665 . ?
C2 N1 H1A 109.6 2_665 . ?
C2 N1 H1A 109.6 . . ?
C2 N1 H1B 109.6 2_665 . ?
C2 N1 H1B 109.6 . . ?
H1A N1 H1B 108.1 . . ?
O2 C1 O1 120.7(5) . . ?
O2 C1 C2 119.1(5) . . ?
O1 C1 C2 120.3(5) . . ?
O2 C1 Np1 56.2(3) . . ?
O1 C1 Np1 64.5(3) . . ?
C2 C1 Np1 175.3(4) . . ?
N1 C2 C1 113.8(4) . . ?
N1 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
N1 C2 H2B 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C1 O2 Np1 99.1(4) . . ?

_refine_diff_density_max         3.682
_refine_diff_density_min         -2.614
_refine_diff_density_rms         0.292


_exptl_crystal_recrystallization_method 'Slow evaporation'
