# 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 2017

####################################################################### 
# 
# 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_bo2322
_database_code_depnum_ccdc_archive 'CCDC 1018388'
_audit_update_record             
;
2014-08-07 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H2 Cl2 N4'
_chemical_formula_weight         164.99

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   8.814(3)
_cell_length_b                   9.208(3)
_cell_length_c                   14.261(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1157.4(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    4243
_cell_measurement_theta_min      2,633
_cell_measurement_theta_max      31.492

_exptl_crystal_description       Chip
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.894
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    1.016
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.6412
_exptl_absorpt_correction_T_max  0.7435
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10549
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         31.48
_reflns_number_total             1914
_reflns_number_gt                1843
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0586P)²+0.6800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   none
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0038(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1914
_refine_ls_number_parameters     83
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1023
_refine_ls_wR_factor_gt          0.0997
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.72296(5) 0.48553(5) 0.03537(3) 0.03020(14) Uani 1 1 d . . .
Cl2 Cl 0.54303(5) 0.73574(5) 0.36797(3) 0.02955(13) Uani 1 1 d . . .
N1 N 0.78133(16) 0.47249(15) 0.21862(10) 0.0269(3) Uani 1 1 d . . .
N2 N 0.73570(16) 0.53712(15) 0.30345(10) 0.0264(3) Uani 1 1 d . . .
N3 N 0.51112(17) 0.72524(15) 0.13913(9) 0.0233(3) Uani 1 1 d . . .
N4 N 0.43668(19) 0.79810(18) 0.09802(11) 0.0340(3) Uani 1 1 d . . .
C1 C 0.70318(18) 0.53116(16) 0.15082(11) 0.0222(3) Uani 1 1 d . . .
C2 C 0.60299(17) 0.63751(15) 0.18706(10) 0.0212(3) Uani 1 1 d . . .
C3 C 0.63128(17) 0.63363(15) 0.28462(10) 0.0220(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0342(2) 0.0329(2) 0.0235(2) -0.00549(14) 0.00532(14) -0.00117(15)
Cl2 0.0347(2) 0.0317(2) 0.0222(2) -0.00380(13) 0.00408(14) 0.00220(15)
N1 0.0289(7) 0.0241(6) 0.0278(7) -0.0002(5) 0.0006(5) 0.0030(5)
N2 0.0303(7) 0.0254(6) 0.0234(6) 0.0030(5) -0.0017(5) 0.0025(5)
N3 0.0254(6) 0.0246(6) 0.0199(6) -0.0007(4) 0.0001(5) 0.0009(5)
N4 0.0372(8) 0.0374(8) 0.0276(7) 0.0022(6) -0.0026(6) 0.0104(6)
C1 0.0237(6) 0.0207(6) 0.0222(6) -0.0011(5) 0.0027(5) -0.0024(5)
C2 0.0224(6) 0.0212(6) 0.0201(6) 0.0012(5) -0.0006(5) 0.0002(5)
C3 0.0246(6) 0.0213(6) 0.0203(6) 0.0008(5) 0.0009(5) -0.0022(5)

_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
Cl1 C1 1.7081(16) . ?
Cl2 C3 1.7035(15) . ?
N1 C1 1.304(2) . ?
N1 N2 1.407(2) . ?
N2 C3 1.3072(19) . ?
N3 N4 1.106(2) . ?
N3 C2 1.3325(19) . ?
C1 C2 1.416(2) . ?
C2 C3 1.414(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 N2 108.13(13) . . ?
C3 N2 N1 108.19(13) . . ?
N4 N3 C2 178.72(18) . . ?
N1 C1 C2 110.19(14) . . ?
N1 C1 Cl1 123.97(12) . . ?
C2 C1 Cl1 125.83(12) . . ?
N3 C2 C3 128.85(14) . . ?
N3 C2 C1 127.66(14) . . ?
C3 C2 C1 103.39(13) . . ?
N2 C3 C2 110.08(13) . . ?
N2 C3 Cl2 123.60(12) . . ?
C2 C3 Cl2 126.31(12) . . ?

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
C1 N1 N2 C3 -0.18(18) . . . . ?
N2 N1 C1 C2 0.29(17) . . . . ?
N2 N1 C1 Cl1 179.58(11) . . . . ?
N4 N3 C2 C3 144(8) . . . . ?
N4 N3 C2 C1 -31(8) . . . . ?
N1 C1 C2 N3 176.25(15) . . . . ?
Cl1 C1 C2 N3 -3.0(2) . . . . ?
N1 C1 C2 C3 -0.29(17) . . . . ?
Cl1 C1 C2 C3 -179.56(11) . . . . ?
N1 N2 C3 C2 -0.01(17) . . . . ?
N1 N2 C3 Cl2 179.11(11) . . . . ?
N3 C2 C3 N2 -176.31(15) . . . . ?
C1 C2 C3 N2 0.18(17) . . . . ?
N3 C2 C3 Cl2 4.6(2) . . . . ?
C1 C2 C3 Cl2 -178.91(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        31.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_bo2541
_database_code_depnum_ccdc_archive 'CCDC 1018387'
_audit_update_record             
;
2017-01-05 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        4-diazo-3,5-dinitropyrazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H0 N6 O4'
_chemical_formula_weight         184.09

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   11.382(3)
_cell_length_b                   10.234(2)
_cell_length_c                   12.054(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.625(3)
_cell_angle_gamma                90.00
_cell_volume                     1322.4(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    4515
_cell_measurement_theta_min      2.680
_cell_measurement_theta_max      29.131

_exptl_crystal_description       Chunk
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.849
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.9195
_exptl_absorpt_correction_T_max  0.9538
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13874
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         29.13
_reflns_number_total             3539
_reflns_number_gt                3021
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0569P)²+0.1130P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   none
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3539
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.49413(10) 0.31928(11) 0.47464(10) 0.0308(2) Uani 1 1 d . . .
N2 N 0.46910(9) 0.41342(11) 0.38858(10) 0.0294(2) Uani 1 1 d . . .
N3 N 0.16693(9) 0.35210(9) 0.40213(8) 0.0235(2) Uani 1 1 d . . .
N4 N 0.06860(10) 0.34282(11) 0.39537(10) 0.0339(3) Uani 1 1 d . . .
N5 N 0.38203(11) 0.19832(11) 0.57971(10) 0.0328(3) Uani 1 1 d . . .
N6 N 0.29303(10) 0.53481(10) 0.26329(9) 0.0273(2) Uani 1 1 d . . .
N7 N 0.70079(10) 0.89946(10) 0.02447(9) 0.0286(2) Uani 1 1 d . . .
N8 N 0.73958(10) 0.97977(10) 0.12210(9) 0.0284(2) Uani 1 1 d . . .
N9 N 0.89949(9) 0.68581(10) 0.23712(9) 0.0243(2) Uani 1 1 d . . .
N10 N 0.95634(11) 0.60509(11) 0.28810(10) 0.0343(3) Uani 1 1 d . . .
N11 N 0.74393(10) 0.68161(10) -0.02843(9) 0.0277(2) Uani 1 1 d . . .
N12 N 0.88488(10) 0.96944(11) 0.32165(10) 0.0320(3) Uani 1 1 d . . .
O1 O 0.27953(10) 0.18764(10) 0.59129(9) 0.0415(3) Uani 1 1 d . . .
O2 O 0.47659(11) 0.14082(11) 0.63700(10) 0.0537(3) Uani 1 1 d . . .
O3 O 0.17918(9) 0.54379(9) 0.23166(8) 0.0349(2) Uani 1 1 d . . .
O4 O 0.36177(10) 0.59991(10) 0.22641(9) 0.0415(3) Uani 1 1 d . . .
O5 O 0.79678(10) 0.57929(9) 0.01131(8) 0.0384(2) Uani 1 1 d . . .
O6 O 0.68705(10) 0.70389(10) -0.13216(8) 0.0403(3) Uani 1 1 d . . .
O7 O 0.95663(10) 0.89635(11) 0.39299(9) 0.0450(3) Uani 1 1 d . . .
O8 O 0.86898(10) 1.08553(10) 0.33544(10) 0.0462(3) Uani 1 1 d . . .
C1 C 0.38868(11) 0.28887(11) 0.48992(10) 0.0245(2) Uani 1 1 d . . .
C2 C 0.28900(10) 0.36011(11) 0.41340(10) 0.0212(2) Uani 1 1 d . . .
C3 C 0.34923(11) 0.43793(11) 0.35285(10) 0.0233(2) Uani 1 1 d . . .
C4 C 0.75427(11) 0.78539(11) 0.05534(10) 0.0234(2) Uani 1 1 d . . .
C5 C 0.82824(10) 0.78393(11) 0.17404(10) 0.0222(2) Uani 1 1 d . . .
C6 C 0.81555(11) 0.91177(11) 0.20920(10) 0.0243(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0260(5) 0.0296(6) 0.0347(6) 0.0007(4) 0.0075(4) 0.0030(4)
N2 0.0263(5) 0.0290(5) 0.0345(6) -0.0009(4) 0.0125(4) 0.0004(4)
N3 0.0265(5) 0.0194(5) 0.0252(5) -0.0017(4) 0.0092(4) -0.0006(4)
N4 0.0284(6) 0.0305(6) 0.0439(7) -0.0018(5) 0.0136(5) -0.0017(4)
N5 0.0436(6) 0.0231(5) 0.0279(6) 0.0024(4) 0.0069(5) 0.0012(4)
N6 0.0363(6) 0.0217(5) 0.0255(5) -0.0008(4) 0.0124(4) -0.0002(4)
N7 0.0353(6) 0.0249(5) 0.0263(5) 0.0036(4) 0.0111(4) 0.0039(4)
N8 0.0342(5) 0.0228(5) 0.0299(6) 0.0020(4) 0.0131(4) 0.0050(4)
N9 0.0235(5) 0.0244(5) 0.0254(5) -0.0003(4) 0.0088(4) 0.0000(4)
N10 0.0313(6) 0.0302(6) 0.0372(6) 0.0028(5) 0.0059(5) 0.0045(5)
N11 0.0324(6) 0.0247(5) 0.0264(5) -0.0009(4) 0.0104(4) -0.0025(4)
N12 0.0308(5) 0.0318(6) 0.0341(6) -0.0083(4) 0.0119(4) 0.0037(4)
O1 0.0568(7) 0.0321(5) 0.0438(6) 0.0072(4) 0.0276(5) 0.0003(4)
O2 0.0516(7) 0.0448(7) 0.0486(7) 0.0198(5) -0.0046(5) 0.0058(5)
O3 0.0341(5) 0.0349(5) 0.0338(5) 0.0044(4) 0.0088(4) 0.0086(4)
O4 0.0503(6) 0.0343(6) 0.0444(6) 0.0104(4) 0.0216(5) -0.0069(4)
O5 0.0538(6) 0.0227(5) 0.0369(5) -0.0007(4) 0.0126(4) 0.0057(4)
O6 0.0507(6) 0.0403(6) 0.0238(5) -0.0030(4) 0.0047(4) 0.0019(4)
O7 0.0430(6) 0.0461(6) 0.0353(5) -0.0089(4) -0.0008(4) 0.0133(5)
O8 0.0513(6) 0.0338(6) 0.0511(6) -0.0181(5) 0.0139(5) 0.0087(5)
C1 0.0271(6) 0.0203(5) 0.0238(6) -0.0011(4) 0.0056(4) 0.0014(4)
C2 0.0226(5) 0.0194(5) 0.0222(5) -0.0023(4) 0.0084(4) 0.0003(4)
C3 0.0270(6) 0.0204(5) 0.0240(6) -0.0029(4) 0.0107(4) -0.0005(4)
C4 0.0283(6) 0.0206(5) 0.0230(6) 0.0020(4) 0.0111(4) -0.0006(4)
C5 0.0250(5) 0.0195(5) 0.0241(6) 0.0024(4) 0.0111(4) 0.0004(4)
C6 0.0270(6) 0.0224(5) 0.0268(6) -0.0005(4) 0.0135(5) 0.0010(4)

_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 C1 1.3115(16) . ?
N1 N2 1.3736(15) . ?
N2 C3 1.3096(15) . ?
N3 N4 1.0986(14) . ?
N3 C2 1.3523(15) . ?
N5 O2 1.2175(15) . ?
N5 O1 1.2255(15) . ?
N5 C1 1.4459(16) . ?
N6 O4 1.2194(14) . ?
N6 O3 1.2252(14) . ?
N6 C3 1.4470(15) . ?
N7 C4 1.3114(15) . ?
N7 N8 1.3807(15) . ?
N8 C6 1.3131(15) . ?
N9 N10 1.1007(14) . ?
N9 C5 1.3527(14) . ?
N11 O6 1.2209(14) . ?
N11 O5 1.2224(14) . ?
N11 C4 1.4427(15) . ?
N12 O8 1.2215(14) . ?
N12 O7 1.2224(15) . ?
N12 C6 1.4456(16) . ?
C1 C2 1.4023(15) . ?
C2 C3 1.4046(16) . ?
C4 C5 1.3953(17) . ?
C5 C6 1.3975(16) . ?

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 N2 107.76(10) . . ?
C3 N2 N1 108.16(10) . . ?
N4 N3 C2 177.95(12) . . ?
O2 N5 O1 125.89(12) . . ?
O2 N5 C1 118.41(12) . . ?
O1 N5 C1 115.69(11) . . ?
O4 N6 O3 125.91(11) . . ?
O4 N6 C3 117.99(11) . . ?
O3 N6 C3 116.10(10) . . ?
C4 N7 N8 107.63(10) . . ?
C6 N8 N7 107.59(10) . . ?
N10 N9 C5 179.22(13) . . ?
O6 N11 O5 125.67(11) . . ?
O6 N11 C4 118.02(10) . . ?
O5 N11 C4 116.27(10) . . ?
O8 N12 O7 126.44(12) . . ?
O8 N12 C6 117.74(11) . . ?
O7 N12 C6 115.79(11) . . ?
N1 C1 C2 111.14(11) . . ?
N1 C1 N5 122.52(11) . . ?
C2 C1 N5 126.25(11) . . ?
N3 C2 C1 127.70(11) . . ?
N3 C2 C3 130.27(10) . . ?
C1 C2 C3 102.02(10) . . ?
N2 C3 C2 110.91(10) . . ?
N2 C3 N6 121.81(11) . . ?
C2 C3 N6 127.27(11) . . ?
N7 C4 C5 111.30(10) . . ?
N7 C4 N11 122.39(11) . . ?
C5 C4 N11 126.09(11) . . ?
N9 C5 C4 128.73(11) . . ?
N9 C5 C6 128.90(11) . . ?
C4 C5 C6 102.28(10) . . ?
N8 C6 C5 111.16(11) . . ?
N8 C6 N12 122.60(11) . . ?
C5 C6 N12 125.95(11) . . ?

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
C1 N1 N2 C3 -0.32(13) . . . . ?
C4 N7 N8 C6 0.05(13) . . . . ?
N2 N1 C1 C2 0.91(13) . . . . ?
N2 N1 C1 N5 -175.97(10) . . . . ?
O2 N5 C1 N1 -5.78(18) . . . . ?
O1 N5 C1 N1 173.72(11) . . . . ?
O2 N5 C1 C2 177.83(12) . . . . ?
O1 N5 C1 C2 -2.67(18) . . . . ?
N4 N3 C2 C1 -2(4) . . . . ?
N4 N3 C2 C3 177(100) . . . . ?
N1 C1 C2 N3 178.16(11) . . . . ?
N5 C1 C2 N3 -5.10(19) . . . . ?
N1 C1 C2 C3 -1.08(13) . . . . ?
N5 C1 C2 C3 175.65(11) . . . . ?
N1 N2 C3 C2 -0.39(13) . . . . ?
N1 N2 C3 N6 179.01(10) . . . . ?
N3 C2 C3 N2 -178.34(11) . . . . ?
C1 C2 C3 N2 0.87(13) . . . . ?
N3 C2 C3 N6 2.3(2) . . . . ?
C1 C2 C3 N6 -178.48(10) . . . . ?
O4 N6 C3 N2 -4.54(17) . . . . ?
O3 N6 C3 N2 175.67(11) . . . . ?
O4 N6 C3 C2 174.76(12) . . . . ?
O3 N6 C3 C2 -5.04(17) . . . . ?
N8 N7 C4 C5 1.14(13) . . . . ?
N8 N7 C4 N11 -173.78(10) . . . . ?
O6 N11 C4 N7 2.86(17) . . . . ?
O5 N11 C4 N7 -179.19(11) . . . . ?
O6 N11 C4 C5 -171.28(11) . . . . ?
O5 N11 C4 C5 6.67(18) . . . . ?
N10 N9 C5 C4 -55(9) . . . . ?
N10 N9 C5 C6 129(9) . . . . ?
N7 C4 C5 N9 -178.51(11) . . . . ?
N11 C4 C5 N9 -3.82(19) . . . . ?
N7 C4 C5 C6 -1.77(13) . . . . ?
N11 C4 C5 C6 172.92(11) . . . . ?
N7 N8 C6 C5 -1.21(13) . . . . ?
N7 N8 C6 N12 172.95(10) . . . . ?
N9 C5 C6 N8 178.53(11) . . . . ?
C4 C5 C6 N8 1.80(13) . . . . ?
N9 C5 C6 N12 4.6(2) . . . . ?
C4 C5 C6 N12 -172.12(11) . . . . ?
O8 N12 C6 N8 1.59(18) . . . . ?
O7 N12 C6 N8 -176.68(12) . . . . ?
O8 N12 C6 C5 174.85(12) . . . . ?
O7 N12 C6 C5 -3.42(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        29.13
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.044
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3oh54
_database_code_depnum_ccdc_archive 'CCDC 1018389'
_audit_update_record             
;
2014-08-07 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;
_audit_creation_date             2014-03-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4779)
;
_shelxl_version_number           2013-2
_chemical_name_common            NCDAP
_chemical_name_systematic        
'3-nitro-5-carbonyl-4-diazopyrazolate zwitterion'
_chemical_formula_moiety         'C3 H N5 O3'
_chemical_formula_sum            'C3 H N5 O3'
_chemical_formula_weight         155.09
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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      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                   5.5357(4)
_cell_length_b                   9.1337(7)
_cell_length_c                   11.5261(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.852(6)
_cell_angle_gamma                90
_cell_volume                     582.47(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1494
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.5780
_cell_measurement_theta_min      4.4330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5344
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.570
_diffrn_reflns_theta_min         3.537
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4713
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0578169000
_diffrn_orient_matrix_UB_12      0.0615478000
_diffrn_orient_matrix_UB_13      0.0261147000
_diffrn_orient_matrix_UB_21      -0.0488337000
_diffrn_orient_matrix_UB_22      0.0455049000
_diffrn_orient_matrix_UB_23      -0.0447679000
_diffrn_orient_matrix_UB_31      -0.1035527000
_diffrn_orient_matrix_UB_32      0.0129337000
_diffrn_orient_matrix_UB_33      0.0332280000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                995
_reflns_number_total             1468
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1468
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0547P)²+0.0045P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1135
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.2347(2) 0.80501(14) 0.83004(11) 0.0511(4) Uani 1 1 d . . . . .
O2 O 1.0048(2) 1.03419(15) 0.65041(10) 0.0475(4) Uani 1 1 d . . . . .
O3 O 0.1336(2) 0.69111(15) 0.67080(12) 0.0565(4) Uani 1 1 d . . . . .
N4 N 0.6956(2) 0.94717(16) 0.84557(12) 0.0389(4) Uani 1 1 d . . . . .
N5 N 0.5147(2) 0.81409(15) 0.56797(11) 0.0393(4) Uani 1 1 d . . . . .
C6 C 0.8219(3) 0.95828(18) 0.64518(13) 0.0350(4) Uani 1 1 d . . . . .
N7 N 0.2675(2) 0.76897(16) 0.72953(12) 0.0397(4) Uani 1 1 d . . . . .
N8 N 0.7216(2) 0.89094(16) 0.54930(11) 0.0393(4) Uani 1 1 d . . . . .
H8 H 0.7841 0.8965 0.4821 0.047 Uiso 1 1 calc R . . . .
C9 C 0.4795(3) 0.82840(17) 0.67790(13) 0.0335(4) Uani 1 1 d . . . . .
C10 C 0.6595(3) 0.91442(18) 0.73404(13) 0.0348(4) Uani 1 1 d . . . . .
N11 N 0.7365(3) 0.9787(2) 0.93676(14) 0.0584(5) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0541(8) 0.0548(8) 0.0455(7) 0.0082(6) 0.0212(6) 0.0031(6)
O2 0.0450(7) 0.0553(8) 0.0426(7) -0.0009(6) 0.0088(5) -0.0147(6)
O3 0.0469(8) 0.0534(8) 0.0693(9) 0.0009(7) 0.0047(6) -0.0156(6)
N4 0.0392(8) 0.0455(9) 0.0324(8) 0.0017(6) 0.0075(6) 0.0032(6)
N5 0.0397(8) 0.0415(8) 0.0371(8) -0.0005(6) 0.0059(6) -0.0040(6)
C6 0.0352(9) 0.0365(9) 0.0336(9) 0.0042(7) 0.0064(6) -0.0002(7)
N7 0.0372(8) 0.0357(8) 0.0469(9) 0.0073(7) 0.0091(6) 0.0009(6)
N8 0.0396(8) 0.0486(9) 0.0303(7) 0.0000(6) 0.0098(5) -0.0061(6)
C9 0.0325(8) 0.0330(8) 0.0354(8) 0.0020(7) 0.0069(6) 0.0013(6)
C10 0.0378(9) 0.0374(9) 0.0295(8) -0.0007(7) 0.0066(6) 0.0011(7)
N11 0.0608(10) 0.0768(13) 0.0378(9) -0.0063(8) 0.0040(7) -0.0005(9)

_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 N7 1.2235(17) . ?
O2 C6 1.2271(19) . ?
O3 N7 1.2168(19) . ?
N4 C10 1.329(2) . ?
N4 N11 1.1060(19) . ?
N5 N8 1.3663(18) . ?
N5 C9 1.2947(19) . ?
C6 N8 1.367(2) . ?
C6 C10 1.441(2) . ?
N7 C9 1.439(2) . ?
C9 C10 1.410(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
N11 N4 C10 176.14(17) . . ?
C9 N5 N8 104.81(12) . . ?
O2 C6 N8 127.37(14) . . ?
O2 C6 C10 130.90(15) . . ?
N8 C6 C10 101.72(13) . . ?
O1 N7 C9 115.97(14) . . ?
O3 N7 O1 125.29(14) . . ?
O3 N7 C9 118.72(14) . . ?
N5 N8 C6 115.12(12) . . ?
N5 C9 N7 121.13(14) . . ?
N5 C9 C10 112.28(13) . . ?
C10 C9 N7 126.45(14) . . ?
N4 C10 C6 123.18(15) . . ?
N4 C10 C9 130.66(14) . . ?
C9 C10 C6 106.05(13) . . ?

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 N7 C9 N5 -170.49(14) . . . . ?
O1 N7 C9 C10 4.9(2) . . . . ?
O2 C6 N8 N5 -179.25(16) . . . . ?
O2 C6 C10 N4 -3.8(3) . . . . ?
O2 C6 C10 C9 179.53(17) . . . . ?
O3 N7 C9 N5 7.8(2) . . . . ?
O3 N7 C9 C10 -176.81(15) . . . . ?
N5 C9 C10 N4 -175.60(16) . . . . ?
N5 C9 C10 C6 0.67(19) . . . . ?
N7 C9 C10 N4 8.7(3) . . . . ?
N7 C9 C10 C6 -175.02(14) . . . . ?
N8 N5 C9 N7 176.15(14) . . . . ?
N8 N5 C9 C10 0.20(18) . . . . ?
N8 C6 C10 N4 175.41(15) . . . . ?
N8 C6 C10 C9 -1.21(17) . . . . ?
C9 N5 N8 C6 -1.10(18) . . . . ?
C10 C6 N8 N5 1.46(18) . . . . ?

_shelx_res_file                  
;
TITL 3OH54 in P21/n #14
CELL 0.71073 5.535683 9.133658 11.526133 90 91.8516 90
ZERR 4 0.000397 0.00065 0.000799 0 0.0063 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
 
SFAC C H N O
UNIT 12 4 20 12
 
L.S. 20
PLAN  20
REM reset to P21/n #14
BOND
fmap 2
MORE -1
CONF
ACTA 52
REM <HKL>D:/Data/3OH54/3OH54.hkl</HKL>
 
WGHT    0.054700    0.004500
FVAR      10.15927
O1    4    0.234686    0.805006    0.830043    11.00000    0.05413    0.05479 =
         0.04553    0.00816    0.02120    0.00310
O2    4    1.004823    1.034185    0.650409    11.00000    0.04503    0.05533 =
         0.04259   -0.00088    0.00884   -0.01471
O3    4    0.133613    0.691108    0.670805    11.00000    0.04695    0.05339 =
         0.06928    0.00087    0.00466   -0.01559
N4    3    0.695574    0.947171    0.845570    11.00000    0.03923    0.04545 =
         0.03244    0.00173    0.00755    0.00318
N5    3    0.514664    0.814087    0.567970    11.00000    0.03970    0.04146 =
         0.03711   -0.00047    0.00587   -0.00403
C6    1    0.821886    0.958284    0.645177    11.00000    0.03519    0.03653 =
         0.03356    0.00422    0.00638   -0.00020
N7    3    0.267473    0.768970    0.729531    11.00000    0.03716    0.03570 =
         0.04687    0.00731    0.00911    0.00094
N8    3    0.721571    0.890942    0.549296    11.00000    0.03956    0.04864 =
         0.03027   -0.00003    0.00984   -0.00607
AFIX  43
H8    2    0.784132    0.896539    0.482108    11.00000   -1.20000
AFIX   0
C9    1    0.479504    0.828405    0.677897    11.00000    0.03246    0.03301 =
         0.03537    0.00203    0.00695    0.00134
C10   1    0.659499    0.914423    0.734044    11.00000    0.03780    0.03742 =
         0.02954   -0.00075    0.00660    0.00108
N11   3    0.736453    0.978672    0.936756    11.00000    0.06084    0.07683 =
         0.03779   -0.00627    0.00404   -0.00049
HKLF 4
 
REM  3OH54 in P21/n #14
REM R1 =  0.0456 for     995 Fo > 4sig(Fo)  and  0.0749 for all    1468 data
REM    100 parameters refined using      0 restraints
 
END  
     
WGHT      0.0547      0.0045 

REM Highest difference peak  0.249,  deepest hole -0.364,  1-sigma level  0.086
Q1    1   0.9764  0.7532  0.4625  11.00000  0.05    0.25
Q2    1   0.0047  0.7645  0.5511  11.00000  0.05    0.22
Q3    1   0.5272  1.0285  0.5545  11.00000  0.05    0.22
Q4    1   0.0029  0.6681  0.5430  11.00000  0.05    0.20
Q5    1   0.2804  0.9418  0.6023  11.00000  0.05    0.20
Q6    1   0.5593  0.7986  0.9954  11.00000  0.05    0.20
Q7    1   0.1091  0.7391  0.5410  11.00000  0.05    0.19
Q8    1   0.6358  0.9792  0.4186  11.00000  0.05    0.19
Q9    1   1.0944  0.7671  0.4522  11.00000  0.05    0.19
Q10   1   0.3880  0.9568  0.5238  11.00000  0.05    0.19
Q11   1   1.0242  1.0389  0.9226  11.00000  0.05    0.19
Q12   1   0.7792  0.9890  1.0983  11.00000  0.05    0.18
Q13   1   0.7159  0.9811  0.3821  11.00000  0.05    0.18
Q14   1   1.0667  1.0161  0.8839  11.00000  0.05    0.17
Q15   1   0.9916  1.1023  0.8208  11.00000  0.05    0.17
Q16   1   0.3553  0.5914  0.6252  11.00000  0.05    0.17
Q17   1   0.9048  0.9742  1.0343  11.00000  0.05    0.16
Q18   1   0.5947  0.8325  0.7239  11.00000  0.05    0.16
Q19   1   0.2178  0.9498  0.9066  11.00000  0.05    0.16
Q20   1   0.7452  0.7600  0.7005  11.00000  0.05    0.16

REM The information below was added by Olex2.
REM
REM R1 = 0.0456 for 995 Fo > 4sig(Fo) and 0.0749 for all 5532 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.25, deepest hole -0.36
REM Mean Shift 0, Max Shift 0.

REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0749
REM R1_gt = 0.0456
REM wR_ref = 0.1135
REM GOOF = 1.085
REM Shift_max = 0
REM Shift_mean = 0
REM Reflections_all = 5532
REM Reflections_gt = 995
REM Parameters = n/a
REM Hole = -0.36
REM Peak = 0.25
REM Flack = n/a

;
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'

_chemical_properties_physical    Heat-sensitive
