# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_vina_bispentyl_150_07july17_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1563077'
_audit_update_record             
;
2017-07-19 deposited with the CCDC.
2017-07-21 downloaded from the CCDC.
;
_audit_creation_date             2017-07-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H24 Cl N5'
_chemical_formula_sum            'C13 H24 Cl N5'
_chemical_formula_weight         285.82
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

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

_cell_length_a                   5.0652(13)
_cell_length_b                   10.017(3)
_cell_length_c                   15.742(4)
_cell_angle_alpha                97.550(16)
_cell_angle_beta                 97.678(15)
_cell_angle_gamma                99.715(15)
_cell_volume                     770.5(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1586
_cell_measurement_temperature    149.89
_cell_measurement_theta_max      22.619
_cell_measurement_theta_min      2.644
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1519 before and 0.0950 after correction. The Ratio of minimum to maximum transmission is 0.6489. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.061
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2348
_diffrn_reflns_av_unetI/netI     0.1245
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33877
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.089
_diffrn_ambient_temperature      149.89
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1509
_reflns_number_total             2706
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2706
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1466
_refine_ls_R_factor_gt           0.0645
_refine_ls_restrained_S_all      1.035
_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)+(0.0429P)²+0.4159P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1416
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,
 H10B), C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N5(H5)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.0898(2) 0.86733(10) 0.62419(7) 0.0326(3) Uani 1 1 d . . . . .
N1 N 0.6760(6) 0.8582(3) 0.5072(2) 0.0223(8) Uani 1 1 d . . . . .
N2 N 0.4870(6) 0.6578(3) 0.40065(19) 0.0230(8) Uani 1 1 d . . . . .
N3 N 0.8752(6) 0.6584(3) 0.5069(2) 0.0224(8) Uani 1 1 d . . . . .
N4 N 0.3139(5) 0.8549(3) 0.40130(19) 0.0233(8) Uani 1 1 d . . . . .
H4 H 0.315163 0.939815 0.424797 0.028 Uiso 1 1 calc R . . . .
N5 N 0.6817(6) 0.4675(3) 0.4059(2) 0.0247(8) Uani 1 1 d . . . . .
H5 H 0.806173 0.426379 0.429875 0.030 Uiso 1 1 calc R . . . .
C1 C 0.8516(7) 0.7846(4) 0.5352(2) 0.0240(9) Uani 1 1 d . . . . .
C2 C 0.4952(7) 0.7880(4) 0.4366(2) 0.0240(10) Uani 1 1 d . . . . .
C3 C 0.6791(7) 0.5980(4) 0.4386(3) 0.0226(9) Uani 1 1 d . . . . .
C4 C 0.1143(7) 0.7930(4) 0.3255(2) 0.0269(10) Uani 1 1 d . . . . .
H4A H -0.031167 0.847576 0.320568 0.032 Uiso 1 1 calc R . . . .
H4B H 0.031094 0.699646 0.333528 0.032 Uiso 1 1 calc R . . . .
C5 C 0.2315(8) 0.7833(4) 0.2417(3) 0.0299(10) Uani 1 1 d . . . . .
H5A H 0.087847 0.731654 0.194291 0.036 Uiso 1 1 calc R . . . .
H5B H 0.378310 0.729638 0.247338 0.036 Uiso 1 1 calc R . . . .
C6 C 0.3442(8) 0.9192(4) 0.2156(3) 0.0345(11) Uani 1 1 d . . . . .
H6A H 0.191320 0.963604 0.196077 0.041 Uiso 1 1 calc R . . . .
H6B H 0.456197 0.979775 0.267139 0.041 Uiso 1 1 calc R . . . .
C7 C 0.5147(8) 0.9063(4) 0.1441(3) 0.0405(12) Uani 1 1 d . . . . .
H7A H 0.401366 0.847155 0.092220 0.049 Uiso 1 1 calc R . . . .
H7B H 0.665020 0.859990 0.163170 0.049 Uiso 1 1 calc R . . . .
C8 C 0.6337(9) 1.0418(5) 0.1185(3) 0.0521(13) Uani 1 1 d . . . . .
H8A H 0.486454 1.085233 0.094938 0.078 Uiso 1 1 calc GR . . . .
H8B H 0.748852 1.025561 0.074355 0.078 Uiso 1 1 calc GR . . . .
H8C H 0.742614 1.102308 0.169668 0.078 Uiso 1 1 calc GR . . . .
C9 C 0.4870(7) 0.3928(4) 0.3329(2) 0.0240(10) Uani 1 1 d . . . . .
H9A H 0.306465 0.414420 0.339532 0.029 Uiso 1 1 calc R . . . .
H9B H 0.475424 0.293363 0.333881 0.029 Uiso 1 1 calc R . . . .
C10 C 0.5517(7) 0.4234(4) 0.2459(2) 0.0277(10) Uani 1 1 d . . . . .
H10A H 0.713592 0.385445 0.233808 0.033 Uiso 1 1 calc R . . . .
H10B H 0.596280 0.523974 0.248002 0.033 Uiso 1 1 calc R . . . .
C11 C 0.3194(8) 0.3637(4) 0.1730(3) 0.0330(11) Uani 1 1 d . . . . .
H11A H 0.158560 0.402236 0.185395 0.040 Uiso 1 1 calc R . . . .
H11B H 0.273990 0.263354 0.171875 0.040 Uiso 1 1 calc R . . . .
C12 C 0.3756(8) 0.3905(5) 0.0840(3) 0.0421(12) Uani 1 1 d . . . . .
H12A H 0.539361 0.354376 0.072053 0.050 Uiso 1 1 calc R . . . .
H12B H 0.414837 0.490804 0.084299 0.050 Uiso 1 1 calc R . . . .
C13 C 0.1421(9) 0.3258(5) 0.0116(3) 0.0540(14) Uani 1 1 d . . . . .
H13A H 0.190909 0.346767 -0.044073 0.081 Uiso 1 1 calc GR . . . .
H13B H -0.019865 0.362812 0.022078 0.081 Uiso 1 1 calc GR . . . .
H13C H 0.104623 0.226219 0.009879 0.081 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.736(4) . ?
N1 C1 1.315(4) . ?
N1 C2 1.369(5) . ?
N2 C2 1.343(4) . ?
N2 C3 1.341(4) . ?
N3 C1 1.314(4) . ?
N3 C3 1.360(5) . ?
N4 C2 1.331(4) . ?
N4 C4 1.451(4) . ?
N5 C3 1.343(4) . ?
N5 C9 1.441(4) . ?
C4 C5 1.515(5) . ?
C5 C6 1.515(5) . ?
C6 C7 1.513(5) . ?
C7 C8 1.517(5) . ?
C9 C10 1.509(5) . ?
C10 C11 1.510(5) . ?
C11 C12 1.514(5) . ?
C12 C13 1.519(6) . ?

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 C2 112.0(3) . . ?
C3 N2 C2 114.5(3) . . ?
C1 N3 C3 112.0(3) . . ?
C2 N4 C4 122.3(3) . . ?
C3 N5 C9 122.1(3) . . ?
N1 C1 Cl1 114.7(3) . . ?
N3 C1 Cl1 114.8(3) . . ?
N3 C1 N1 130.5(4) . . ?
N2 C2 N1 125.2(3) . . ?
N4 C2 N1 116.9(3) . . ?
N4 C2 N2 117.9(4) . . ?
N2 C3 N3 125.7(3) . . ?
N2 C3 N5 117.5(3) . . ?
N5 C3 N3 116.7(3) . . ?
N4 C4 C5 113.4(3) . . ?
C4 C5 C6 115.4(3) . . ?
C7 C6 C5 113.7(3) . . ?
C6 C7 C8 114.3(4) . . ?
N5 C9 C10 114.3(3) . . ?
C9 C10 C11 112.5(3) . . ?
C10 C11 C12 114.5(3) . . ?
C11 C12 C13 113.5(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_RINTA01_vina_bispentyl_150_07july17_0m_a 
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: crystals were very thin flakes diffracting essentially to lower angles, so 
the weaker data at higher angles contribute to high Rint.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_roomtemp_a
_database_code_depnum_ccdc_archive 'CCDC 1552796'
_audit_update_record             
;
2017-05-29 deposited with the CCDC.
2017-07-21 downloaded from the CCDC.
;
_audit_creation_date             2017-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H16 Cl N5'
_chemical_formula_sum            'C9 H16 Cl N5'
_chemical_formula_weight         229.72
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

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

_cell_length_a                   5.1163(11)
_cell_length_b                   10.011(2)
_cell_length_c                   12.451(2)
_cell_angle_alpha                93.943(9)
_cell_angle_beta                 96.452(9)
_cell_angle_gamma                100.613(9)
_cell_volume                     620.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1390
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.786
_cell_measurement_theta_min      4.085
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0971 before and 0.0577 after correction. The Ratio of minimum to maximum transmission is 0.7785. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.044
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7336
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.078
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1340
_reflns_number_total             2162
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.779
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2162
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.1136
_refine_ls_R_factor_gt           0.0754
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1179P)²+0.4771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2053
_refine_ls_wR_factor_ref         0.2418
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C5A'-C4 \\sim C5A-C4
 with sigma of 0.02
 C8A'-C7 \\sim C8A-C7
 with sigma of 0.02
 C8A-C7 \\sim C8A'-C7 \\sim C8A-C9A \\sim C8A'-C9A'
 with sigma of 0.02
 C5A-C4 \\sim C5A'-C4 \\sim C5A'-C6A' \\sim C5A-C6A
 with sigma of 0.02
3. Rigid bond restraints
 C8A, C8A'
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C9A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C5A, C5A'
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C6A'
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C7) = Uanis(C8A) = Uanis(C9A)
Uanis(C5A') = Uanis(C6A')
Uanis(C5A') = Uanis(C6A)
5. Rigid body (RIGU) restrains
 C4, C5A, C6A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C4, C5A', C6A'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7, C8A, C9A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7, C8A', C9A'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: H4BC(0.5) H4BD(0.5) H4AA(0.5) H4AB(0.5) C5A(0.5) H5AA(0.5)
 H5AB(0.5) C5A'(0.5) H5AC(0.5) H5AD(0.5) C6A(0.5) H6AA(0.5) H6AB(0.5) H6AC(0.5)
 C6A'(0.5) H6AD(0.5) H6AE(0.5) H6AF(0.5) H7AA(0.5) H7AB(0.5) H7BC(0.5)
 H7BD(0.5) C8A(0.5) H8AA(0.5) H8AB(0.5) C8A'(0.5) H8AC(0.5) H8AD(0.5) C9A(0.5)
 H9AA(0.5) H9AB(0.5) H9AC(0.5) C9A'(0.5) H9AD(0.5) H9AE(0.5) H9AF(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C4(H4BC,H4BD), C4(H4AA,H4AB), C5A(H5AA,H5AB), C5A'(H5AC,H5AD), C7(H7AA,H7AB),
 C7(H7BC,H7BD), C8A(H8AA,H8AB), C8A'(H8AC,H8AD)
7.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N5(H5)
7.c Idealised Me refined as rotating group:
 C6A(H6AA,H6AB,H6AC), C6A'(H6AD,H6AE,H6AF), C9A(H9AA,H9AB,H9AC), C9A'(H9AD,
 H9AE,H9AF)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.0757(2) 0.85712(11) 0.65711(10) 0.0713(5) Uani 1 1 d . . . . .
N1 N 0.8772(7) 0.6599(3) 0.5086(3) 0.0513(9) Uani 1 1 d . . . . .
N2 N 0.5136(7) 0.6716(3) 0.3720(3) 0.0524(9) Uani 1 1 d . . . . .
N3 N 0.6807(7) 0.8578(3) 0.5089(3) 0.0528(9) Uani 1 1 d . . . . .
N4 N 0.7052(7) 0.4823(3) 0.3803(3) 0.0592(10) Uani 1 1 d . . . . .
H4 H 0.8231 0.4417 0.4117 0.071 Uiso 1 1 calc R . . . .
N5 N 0.3375(7) 0.8662(3) 0.3762(3) 0.0571(10) Uani 1 1 d . . . . .
H5 H 0.3345 0.9448 0.4081 0.068 Uiso 1 1 calc R . . . .
C1 C 0.8508(8) 0.7820(4) 0.5453(3) 0.0516(11) Uani 1 1 d . . . . .
C2 C 0.6967(8) 0.6084(4) 0.4207(3) 0.0483(10) Uani 1 1 d . . . . .
C3 C 0.5131(8) 0.7956(4) 0.4192(3) 0.0500(10) Uani 1 1 d . . . . .
C4 C 0.5301(10) 0.4103(5) 0.2879(4) 0.0653(12) Uani 1 1 d D U . . .
H4BC H 0.3564 0.4358 0.2888 0.078 Uiso 0.5 1 calc R . P A 2
H4BD H 0.5058 0.3135 0.2968 0.078 Uiso 0.5 1 calc R . P A 2
H4AA H 0.3570 0.4373 0.2850 0.078 Uiso 0.5 1 calc R . P B 1
H4AB H 0.5033 0.3129 0.2946 0.078 Uiso 0.5 1 calc R . P B 1
C5A C 0.649(5) 0.441(2) 0.1857(10) 0.085(4) Uani 0.5 1 d D U P C 1
H5AA H 0.6569 0.5375 0.1773 0.102 Uiso 0.5 1 calc R . P C 1
H5AB H 0.8317 0.4265 0.1950 0.102 Uiso 0.5 1 calc R . P C 1
C5A' C 0.616(7) 0.432(4) 0.1770(12) 0.137(5) Uani 0.5 1 d D U P C 2
H5AC H 0.6259 0.5263 0.1621 0.165 Uiso 0.5 1 calc R . P C 2
H5AD H 0.7907 0.4085 0.1731 0.165 Uiso 0.5 1 calc R . P C 2
C6A C 0.510(6) 0.363(3) 0.0831(15) 0.137(5) Uani 0.5 1 d D U P C 1
H6AA H 0.6250 0.3753 0.0273 0.206 Uiso 0.5 1 calc GR . P C 1
H6AB H 0.3478 0.3947 0.0616 0.206 Uiso 0.5 1 calc GR . P C 1
H6AC H 0.4674 0.2677 0.0941 0.206 Uiso 0.5 1 calc GR . P C 1
C6A' C 0.407(6) 0.340(3) 0.0965(16) 0.137(5) Uani 0.5 1 d D U P C 2
H6AD H 0.4346 0.3615 0.0243 0.206 Uiso 0.5 1 calc GR . P C 2
H6AE H 0.2319 0.3522 0.1103 0.206 Uiso 0.5 1 calc GR . P C 2
H6AF H 0.4217 0.2463 0.1037 0.206 Uiso 0.5 1 calc GR . P C 2
C7 C 0.1536(11) 0.8190(5) 0.2801(4) 0.0766(12) Uani 1 1 d D U . . .
H7AA H 0.0184 0.8755 0.2779 0.092 Uiso 0.5 1 calc R . P D 1
H7AB H 0.0635 0.7273 0.2897 0.092 Uiso 0.5 1 calc R . P D 1
H7BC H -0.0180 0.8445 0.2874 0.092 Uiso 0.5 1 calc R . P E 2
H7BD H 0.1260 0.7205 0.2675 0.092 Uiso 0.5 1 calc R . P E 2
C8A C 0.246(3) 0.8144(11) 0.1711(8) 0.0766(12) Uani 0.5 1 d D U P F 1
H8AA H 0.3969 0.7685 0.1717 0.092 Uiso 0.5 1 calc R . P F 1
H8AB H 0.1022 0.7645 0.1175 0.092 Uiso 0.5 1 calc R . P F 1
C8A' C 0.275(3) 0.8851(12) 0.1878(8) 0.085(3) Uani 0.5 1 d D U P F 2
H8AC H 0.3111 0.9834 0.2038 0.102 Uiso 0.5 1 calc R . P F 2
H8AD H 0.4443 0.8570 0.1808 0.102 Uiso 0.5 1 calc R . P F 2
C9A C 0.324(2) 0.9545(10) 0.1440(9) 0.0766(12) Uani 0.5 1 d D U P F 1
H9AA H 0.3993 0.9543 0.0769 0.115 Uiso 0.5 1 calc GR . P F 1
H9AB H 0.4540 1.0051 0.2007 0.115 Uiso 0.5 1 calc GR . P F 1
H9AC H 0.1686 0.9961 0.1366 0.115 Uiso 0.5 1 calc GR . P F 1
C9A' C 0.094(3) 0.8477(17) 0.0824(9) 0.123(5) Uani 0.5 1 d D U P F 2
H9AD H 0.1751 0.8949 0.0263 0.185 Uiso 0.5 1 calc GR . P F 2
H9AE H -0.0753 0.8733 0.0896 0.185 Uiso 0.5 1 calc GR . P F 2
H9AF H 0.0671 0.7511 0.0639 0.185 Uiso 0.5 1 calc GR . P F 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.733(4) . ?
N1 C1 1.311(5) . ?
N1 C2 1.355(5) . ?
N2 C2 1.337(5) . ?
N2 C3 1.337(5) . ?
N3 C1 1.320(5) . ?
N3 C3 1.365(5) . ?
N4 H4 0.8600 . ?
N4 C2 1.337(5) . ?
N4 C4 1.437(5) . ?
N5 H5 0.8600 . ?
N5 C3 1.330(5) . ?
N5 C7 1.430(6) . ?
C4 H4BC 0.9700 . ?
C4 H4BD 0.9700 . ?
C4 H4AA 0.9700 . ?
C4 H4AB 0.9700 . ?
C4 C5A 1.497(11) . ?
C4 C5A' 1.512(13) . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C5A C6A 1.485(12) . ?
C5A' H5AC 0.9700 . ?
C5A' H5AD 0.9700 . ?
C5A' C6A' 1.505(14) . ?
C6A H6AA 0.9600 . ?
C6A H6AB 0.9600 . ?
C6A H6AC 0.9600 . ?
C6A' H6AD 0.9600 . ?
C6A' H6AE 0.9600 . ?
C6A' H6AF 0.9600 . ?
C7 H7AA 0.9700 . ?
C7 H7AB 0.9700 . ?
C7 H7BC 0.9700 . ?
C7 H7BD 0.9700 . ?
C7 C8A 1.487(10) . ?
C7 C8A' 1.503(10) . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C8A C9A 1.459(11) . ?
C8A' H8AC 0.9700 . ?
C8A' H8AD 0.9700 . ?
C8A' C9A' 1.500(12) . ?
C9A H9AA 0.9600 . ?
C9A H9AB 0.9600 . ?
C9A H9AC 0.9600 . ?
C9A' H9AD 0.9600 . ?
C9A' H9AE 0.9600 . ?
C9A' H9AF 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 112.2(3) . . ?
C3 N2 C2 114.2(4) . . ?
C1 N3 C3 112.4(3) . . ?
C2 N4 H4 117.9 . . ?
C2 N4 C4 124.1(3) . . ?
C4 N4 H4 117.9 . . ?
C3 N5 H5 118.1 . . ?
C3 N5 C7 123.9(4) . . ?
C7 N5 H5 118.1 . . ?
N1 C1 Cl1 115.6(3) . . ?
N1 C1 N3 129.7(4) . . ?
N3 C1 Cl1 114.7(3) . . ?
N2 C2 N1 126.2(4) . . ?
N2 C2 N4 117.9(4) . . ?
N4 C2 N1 115.9(3) . . ?
N2 C3 N3 125.3(4) . . ?
N5 C3 N2 118.5(4) . . ?
N5 C3 N3 116.2(4) . . ?
N4 C4 H4BC 107.9 . . ?
N4 C4 H4BD 107.9 . . ?
N4 C4 H4AA 109.6 . . ?
N4 C4 H4AB 109.6 . . ?
N4 C4 C5A 110.2(9) . . ?
N4 C4 C5A' 117.4(11) . . ?
H4BC C4 H4BD 107.2 . . ?
H4AA C4 H4AB 108.1 . . ?
C5A C4 H4AA 109.6 . . ?
C5A C4 H4AB 109.6 . . ?
C5A' C4 H4BC 107.9 . . ?
C5A' C4 H4BD 107.9 . . ?
C4 C5A H5AA 108.0 . . ?
C4 C5A H5AB 108.0 . . ?
H5AA C5A H5AB 107.2 . . ?
C6A C5A C4 117.4(14) . . ?
C6A C5A H5AA 108.0 . . ?
C6A C5A H5AB 108.0 . . ?
C4 C5A' H5AC 110.4 . . ?
C4 C5A' H5AD 110.4 . . ?
H5AC C5A' H5AD 108.6 . . ?
C6A' C5A' C4 106.4(16) . . ?
C6A' C5A' H5AC 110.4 . . ?
C6A' C5A' H5AD 110.4 . . ?
C5A C6A H6AA 109.5 . . ?
C5A C6A H6AB 109.5 . . ?
C5A C6A H6AC 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
C5A' C6A' H6AD 109.5 . . ?
C5A' C6A' H6AE 109.5 . . ?
C5A' C6A' H6AF 109.5 . . ?
H6AD C6A' H6AE 109.5 . . ?
H6AD C6A' H6AF 109.5 . . ?
H6AE C6A' H6AF 109.5 . . ?
N5 C7 H7AA 107.0 . . ?
N5 C7 H7AB 107.0 . . ?
N5 C7 H7BC 110.3 . . ?
N5 C7 H7BD 110.3 . . ?
N5 C7 C8A 121.4(6) . . ?
N5 C7 C8A' 106.9(6) . . ?
H7AA C7 H7AB 106.7 . . ?
H7BC C7 H7BD 108.6 . . ?
C8A C7 H7AA 107.0 . . ?
C8A C7 H7AB 107.0 . . ?
C8A' C7 H7BC 110.3 . . ?
C8A' C7 H7BD 110.3 . . ?
C7 C8A H8AA 110.1 . . ?
C7 C8A H8AB 110.1 . . ?
H8AA C8A H8AB 108.4 . . ?
C9A C8A C7 108.0(9) . . ?
C9A C8A H8AA 110.1 . . ?
C9A C8A H8AB 110.1 . . ?
C7 C8A' H8AC 109.2 . . ?
C7 C8A' H8AD 109.2 . . ?
H8AC C8A' H8AD 107.9 . . ?
C9A' C8A' C7 112.0(9) . . ?
C9A' C8A' H8AC 109.2 . . ?
C9A' C8A' H8AD 109.2 . . ?
C8A C9A H9AA 109.5 . . ?
C8A C9A H9AB 109.5 . . ?
C8A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C8A' C9A' H9AD 109.5 . . ?
C8A' C9A' H9AE 109.5 . . ?
C8A' C9A' H9AF 109.5 . . ?
H9AD C9A' H9AE 109.5 . . ?
H9AD C9A' H9AF 109.5 . . ?
H9AE C9A' H9AF 109.5 . . ?

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
N4 C4 C5A C6A 173.0(19) . . . . ?
N4 C4 C5A' C6A' 176.9(19) . . . . ?
N5 C7 C8A C9A -70.3(10) . . . . ?
N5 C7 C8A' C9A' -177.7(10) . . . . ?
C1 N1 C2 N2 1.8(6) . . . . ?
C1 N1 C2 N4 -178.1(3) . . . . ?
C1 N3 C3 N2 0.6(6) . . . . ?
C1 N3 C3 N5 -179.0(3) . . . . ?
C2 N1 C1 Cl1 -179.4(3) . . . . ?
C2 N1 C1 N3 -0.6(6) . . . . ?
C2 N2 C3 N3 0.4(6) . . . . ?
C2 N2 C3 N5 180.0(4) . . . . ?
C2 N4 C4 C5A 88.8(12) . . . . ?
C2 N4 C4 C5A' 88(2) . . . . ?
C3 N2 C2 N1 -1.7(6) . . . . ?
C3 N2 C2 N4 178.2(4) . . . . ?
C3 N3 C1 Cl1 178.3(3) . . . . ?
C3 N3 C1 N1 -0.4(6) . . . . ?
C3 N5 C7 C8A -72.7(7) . . . . ?
C3 N5 C7 C8A' -98.3(7) . . . . ?
C4 N4 C2 N1 179.8(4) . . . . ?
C4 N4 C2 N2 0.0(6) . . . . ?
C7 N5 C3 N2 -2.0(6) . . . . ?
C7 N5 C3 N3 177.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_vina_bis_pentyl_rt_10july17_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1563078'
_audit_update_record             
;
2017-07-19 deposited with the CCDC.
2017-07-21 downloaded from the CCDC.
;
_audit_creation_date             2017-07-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H24 Cl N5'
_chemical_formula_sum            'C13 H24 Cl N5'
_chemical_formula_weight         285.82
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

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

_cell_length_a                   5.120(13)
_cell_length_b                   10.14(3)
_cell_length_c                   17.37(5)
_cell_angle_alpha                91.51(5)
_cell_angle_beta                 93.57(5)
_cell_angle_gamma                101.03(4)
_cell_volume                     883(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    343
_cell_measurement_temperature    299.08
_cell_measurement_theta_max      17.308
_cell_measurement_theta_min      2.352
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1486 before and 0.0848 after correction. The Ratio of minimum to maximum transmission is 0.6044. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.075
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.061
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2565
_diffrn_reflns_av_unetI/netI     0.3992
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10162
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.048
_diffrn_ambient_temperature      299.08
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                712
_reflns_number_total             3060
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3060
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.3897
_refine_ls_R_factor_gt           0.1323
_refine_ls_restrained_S_all      0.993
_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)+(0.1151P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2354
_refine_ls_wR_factor_ref         0.3686
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C0AA-C6
 2.56 with sigma of 0.02
 C2AA-C14
 2.56 with sigma of 0.02
 C6-C9
 2.56 with sigma of 0.02
 C4-C1AA = C9-C14 = C6-C14 = C6-C2AA = C2AA-C0AA
 1.52 with sigma of 0.02
 C8-C1AA
 1.52 with sigma of 0.02
 C8-C4
 2.56 with sigma of 0.02
 C8-C39
 2.56 with sigma of 0.02
 C20A-C1AA
 2.56 with sigma of 0.02
 C8-C20A
 1.52 with sigma of 0.02
 H20B-H39B
 2.225 with sigma of 0.02
 H14A-H9B
 2.138 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C2AA, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1AA, C8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C6, C14
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C8, C20A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C14, C9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C20A, C39
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Secondary CH2 refined with riding coordinates:
 C0AA(H0AA,H0AB), C4(H4A,H4B), C2AA(H2AA,H2AB), C1AA(H1AA,H1AB), C6(H6A,H6B),
 C14(H14A,H14B), C8(H8A,H8B), C20A(H20A,H20B)
4.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N5(H5)
4.c Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl01 Cl -0.0499(5) 0.1559(3) 0.3834(2) 0.1004(15) Uani 1 1 d . . . . .
N1 N 0.3219(16) 0.1430(8) 0.4916(6) 0.075(3) Uani 1 1 d . . . . .
N2 N 0.4675(15) 0.3185(8) 0.5920(5) 0.077(3) Uani 1 1 d . . . . .
N3 N 0.1217(16) 0.3406(8) 0.4917(6) 0.077(3) Uani 1 1 d . . . . .
N4 N 0.6441(16) 0.1261(8) 0.5874(5) 0.074(3) Uani 1 1 d . . . . .
H4 H 0.655431 0.051736 0.564074 0.088 Uiso 1 1 calc R . . . .
N5 N 0.2750(15) 0.5073(8) 0.5865(5) 0.082(3) Uani 1 1 d . . . . .
H5 H 0.164748 0.550664 0.564173 0.099 Uiso 1 1 calc R . . . .
C1 C 0.1573(19) 0.2215(11) 0.4650(6) 0.071(3) Uani 1 1 d . . . . .
C2 C 0.474(2) 0.1990(11) 0.5557(7) 0.073(3) Uani 1 1 d . . . . .
C3 C 0.291(2) 0.3862(10) 0.5559(8) 0.075(4) Uani 1 1 d . . . . .
C0AA C 0.8096(19) 0.1648(10) 0.6585(7) 0.085(4) Uani 1 1 d D . . . .
H0AA H 0.855877 0.262129 0.663531 0.102 Uiso 1 1 calc R . . . .
H0AB H 0.973745 0.130944 0.655838 0.102 Uiso 1 1 calc R . . . .
C4 C 0.430(2) 0.5686(10) 0.6541(7) 0.089(4) Uani 1 1 d D . . . .
H4A H 0.454274 0.665404 0.650012 0.107 Uiso 1 1 calc R . . . .
H4B H 0.605199 0.545435 0.653592 0.107 Uiso 1 1 calc R . . . .
C2AA C 0.671(3) 0.1111(14) 0.7298(8) 0.144(6) Uani 1 1 d D U . . .
H2AA H 0.506430 0.145156 0.731910 0.173 Uiso 1 1 calc R . . . .
H2AB H 0.622608 0.013858 0.723932 0.173 Uiso 1 1 calc R . . . .
C1AA C 0.324(3) 0.5337(13) 0.7312(8) 0.133(5) Uani 1 1 d D U . . .
H1AA H 0.305794 0.437494 0.736771 0.159 Uiso 1 1 calc R . . . .
H1AB H 0.146768 0.554670 0.731887 0.159 Uiso 1 1 calc R . . . .
C6 C 0.832(3) 0.147(2) 0.8054(8) 0.221(10) Uani 1 1 d D U . . .
H6A H 0.886076 0.244273 0.809883 0.266 Uiso 1 1 calc R . . . .
H6B H 0.993737 0.110493 0.803463 0.266 Uiso 1 1 calc R . . . .
C14 C 0.698(5) 0.100(3) 0.8784(10) 0.38(2) Uani 1 1 d D U . . .
H14A H 0.530796 0.131384 0.879343 0.452 Uiso 1 1 calc DR . . . .
H14B H 0.655453 0.001983 0.876228 0.452 Uiso 1 1 calc R . . . .
C39 C 0.579(12) 0.657(4) 0.9432(13) 0.75(5) Uani 1 1 d D U . . .
H39A H 0.575068 0.604058 0.988192 1.129 Uiso 1 1 calc GR . . . .
H39B H 0.519642 0.739285 0.955235 1.129 Uiso 1 1 calc DGR . . . .
H39C H 0.757150 0.677756 0.926959 1.129 Uiso 1 1 calc GR . . . .
C9 C 0.861(7) 0.146(4) 0.9512(11) 0.52(3) Uani 1 1 d D U . . .
H9A H 0.955378 0.077178 0.967763 0.783 Uiso 1 1 calc GR . . . .
H9B H 0.747377 0.164128 0.990317 0.783 Uiso 1 1 calc DGR . . . .
H9C H 0.987298 0.226375 0.942428 0.783 Uiso 1 1 calc GR . . . .
C8 C 0.495(3) 0.6060(19) 0.8010(8) 0.207(8) Uani 1 1 d D U . . .
H8A H 0.669629 0.582492 0.800929 0.248 Uiso 1 1 calc R . . . .
H8B H 0.518073 0.702089 0.794105 0.248 Uiso 1 1 calc R . . . .
C20A C 0.391(6) 0.578(3) 0.8775(10) 0.43(2) Uani 1 1 d D U . . .
H20A H 0.371645 0.482060 0.885981 0.516 Uiso 1 1 calc R . . . .
H20B H 0.216597 0.600959 0.878674 0.516 Uiso 1 1 calc DR . . . .


_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
Cl01 C1 1.752(11) . ?
N1 C1 1.336(11) . ?
N1 C2 1.364(12) . ?
N2 C2 1.358(12) . ?
N2 C3 1.368(12) . ?
N3 C1 1.331(11) . ?
N3 C3 1.381(12) . ?
N4 C2 1.346(11) . ?
N4 C0AA 1.454(11) . ?
N5 C3 1.344(11) . ?
N5 C4 1.432(11) . ?
C0AA C2AA 1.527(12) . ?
C4 C1AA 1.503(12) . ?
C2AA C6 1.506(13) . ?
C1AA C8 1.532(13) . ?
C6 C14 1.528(16) . ?
C14 C9 1.486(16) . ?
C39 C20A 1.55(3) . ?
C8 C20A 1.477(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 C2 112.0(9) . . ?
C2 N2 C3 113.0(10) . . ?
C1 N3 C3 111.7(9) . . ?
C2 N4 C0AA 124.3(9) . . ?
C3 N5 C4 124.1(9) . . ?
N1 C1 Cl01 115.0(9) . . ?
N3 C1 Cl01 114.8(9) . . ?
N3 C1 N1 130.2(10) . . ?
N2 C2 N1 126.9(9) . . ?
N4 C2 N1 116.3(10) . . ?
N4 C2 N2 116.8(11) . . ?
N2 C3 N3 126.2(9) . . ?
N5 C3 N2 117.3(11) . . ?
N5 C3 N3 116.5(10) . . ?
N4 C0AA C2AA 112.5(9) . . ?
N5 C4 C1AA 117.7(10) . . ?
C6 C2AA C0AA 115.0(11) . . ?
C4 C1AA C8 115.1(11) . . ?
C2AA C6 C14 116.8(14) . . ?
C9 C14 C6 114.0(18) . . ?
C20A C8 C1AA 116.5(15) . . ?
C8 C20A C39 112(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_RINTA01_vina_bis_pentyl_rt_10july17_0m_a 
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: Details on refinement from this crystal data collected at room 
temperature (298 K) are given in the experimental section. A  combined brief 
response to these alerts is provided here. 

Crystals were very thin flakes that diffracted very weakly, most of the 
observed reflections were at low angles. To add adversely to this, the 
extensive orientational disorder of the terminal carbons in both the alkyl 
chains at room temperature affected the diffraction profiles and made it 
difficult to locate their positions. This all resulted in the following 
alerts concerning high Rint, low ratio of observed/unique reflections, 
high wR2 value, low bond precision on C-C bonds etc. 
;
_vrf_PLAT020_vina_bis_pentyl_rt_10july17_0m_a 
;
PROBLEM: The value of Rint is greater than 0.12 .........      0.257 Report
RESPONSE:reasons as given above
;
_vrf_PLAT026_vina_bis_pentyl_rt_10july17_0m_a 
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..         23 %     
RESPONSE:reasons as given above
;
_vrf_PLAT084_vina_bis_pentyl_rt_10july17_0m_a 
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.37 Report
RESPONSE: reasons as given above
;
_vrf_PLAT220_vina_bis_pentyl_rt_10july17_0m_a 
;
PROBLEM: Non-Solvent Resd 1   C   Ueq(max)/Ueq(min) Range       10.0 Ratio 
RESPONSE: reasons as given above
;
_vrf_PLAT242_vina_bis_pentyl_rt_10july17_0m_a 
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         C8 Check 
RESPONSE: reasons as given above
;
_vrf_PLAT340_vina_bis_pentyl_rt_10july17_0m_a 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02725 Ang.  
RESPONSE: reasons as given above
;
# end Validation Reply Form
####################################################################### 
# 
# 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_fulldata
_database_code_depnum_ccdc_archive 'CCDC 1552795'
_audit_update_record             
;
2017-05-29 deposited with the CCDC.
2017-07-21 downloaded from the CCDC.
;
_audit_creation_date             2017-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H16 Cl N5'
_chemical_formula_sum            'C9 H16 Cl N5'
_chemical_formula_weight         229.72
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

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

_cell_length_a                   10.280(4)
_cell_length_b                   10.351(3)
_cell_length_c                   12.987(4)
_cell_angle_alpha                98.30(2)
_cell_angle_beta                 112.37(2)
_cell_angle_gamma                108.27(3)
_cell_volume                     1157.5(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1356
_cell_measurement_temperature    147.78
_cell_measurement_theta_max      26.926
_cell_measurement_theta_min      3.195
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1359
_diffrn_reflns_av_unetI/netI     0.1086
_diffrn_reflns_Laue_measured_fraction_full 0.846
_diffrn_reflns_Laue_measured_fraction_max 0.846
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8200
_diffrn_reflns_point_group_measured_fraction_full 0.846
_diffrn_reflns_point_group_measured_fraction_max 0.846
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.470
_diffrn_ambient_temperature      147.78
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.846
_diffrn_measured_fraction_theta_max 0.846
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1909
_reflns_number_total             3457
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3457
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0584
_refine_ls_restrained_S_all      0.964
_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)+(0.0730P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1759
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4A(H4AA,H4AB), C5A(H5AA,H5AB), C7A(H7AA,H7AB), C8A(H8AA,H8AB), C4B(H4BA,
 H4BB), C5B(H5BA,H5BB), C7B(H7BA,H7BB), C8B(H8BA,H8BB)
2.b Aromatic/amide H refined with riding coordinates:
 N4A(H4A), N5A(H5A), N4B(H4B), N5B(H5B)
2.c Idealised Me refined as rotating group:
 C6A(H6AA,H6AB,H6AC), C9A(H9AA,H9AB,H9AC), C6B(H6BA,H6BB,H6BC), C9B(H9BA,H9BB,
 H9BC)
;
_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
Cl1A Cl 1.18521(11) 0.72037(10) 0.66234(9) 0.0338(4) Uani 1 1 d . . . . .
N1A N 1.1025(3) 0.8422(3) 0.5036(3) 0.0226(9) Uani 1 1 d . . . . .
N2A N 0.8396(3) 0.7664(3) 0.3605(3) 0.0241(9) Uani 1 1 d . . . . .
N3A N 0.9067(3) 0.6453(3) 0.5055(3) 0.0221(9) Uani 1 1 d . . . . .
N4A N 1.0343(4) 0.9553(3) 0.3647(3) 0.0253(9) Uani 1 1 d . . . . .
H4A H 1.1327 1.0103 0.3946 0.030 Uiso 1 1 calc R . . . .
N5A N 0.6576(3) 0.5729(3) 0.3662(3) 0.0248(9) Uani 1 1 d . . . . .
H5A H 0.6336 0.5058 0.3985 0.030 Uiso 1 1 calc R . . . .
C1A C 1.0486(4) 0.7380(4) 0.5432(3) 0.0231(11) Uani 1 1 d . . . . .
C2A C 0.9895(4) 0.8517(4) 0.4104(3) 0.0227(11) Uani 1 1 d . . . . .
C3A C 0.8045(4) 0.6646(4) 0.4114(4) 0.0220(11) Uani 1 1 d . . . . .
C4A C 0.9254(5) 0.9793(4) 0.2674(4) 0.0293(12) Uani 1 1 d . . . . .
H4AA H 0.9725 1.0785 0.2669 0.035 Uiso 1 1 calc R . . . .
H4AB H 0.8337 0.9695 0.2794 0.035 Uiso 1 1 calc R . . . .
C5A C 0.8743(5) 0.8781(4) 0.1490(4) 0.0365(14) Uani 1 1 d . . . . .
H5AA H 0.8252 0.7792 0.1492 0.044 Uiso 1 1 calc R . . . .
H5AB H 0.7952 0.8978 0.0888 0.044 Uiso 1 1 calc R . . . .
C6A C 1.0015(5) 0.8870(5) 0.1141(4) 0.0470(15) Uani 1 1 d . . . . .
H6AA H 1.0524 0.9848 0.1147 0.070 Uiso 1 1 calc GR . . . .
H6AB H 0.9573 0.8218 0.0355 0.070 Uiso 1 1 calc GR . . . .
H6AC H 1.0766 0.8602 0.1695 0.070 Uiso 1 1 calc GR . . . .
C7A C 0.5373(4) 0.5803(4) 0.2667(3) 0.0270(11) Uani 1 1 d . . . . .
H7AA H 0.5560 0.6817 0.2737 0.032 Uiso 1 1 calc R . . . .
H7AB H 0.4379 0.5337 0.2677 0.032 Uiso 1 1 calc R . . . .
C8A C 0.5249(5) 0.5099(4) 0.1497(4) 0.0343(13) Uani 1 1 d . . . . .
H8AA H 0.6233 0.5586 0.1478 0.041 Uiso 1 1 calc R . . . .
H8AB H 0.4438 0.5241 0.0866 0.041 Uiso 1 1 calc R . . . .
C9A C 0.4880(5) 0.3498(4) 0.1246(4) 0.0431(15) Uani 1 1 d . . . . .
H9AA H 0.4798 0.3121 0.0477 0.065 Uiso 1 1 calc GR . . . .
H9AB H 0.3903 0.3003 0.1257 0.065 Uiso 1 1 calc GR . . . .
H9AC H 0.5701 0.3347 0.1845 0.065 Uiso 1 1 calc GR . . . .
Cl1B Cl 0.29137(11) 0.27416(10) 0.32588(9) 0.0349(4) Uani 1 1 d . . . . .
N1B N 0.3753(3) 0.1486(3) 0.4817(3) 0.0238(9) Uani 1 1 d . . . . .
N2B N 0.6376(3) 0.2296(3) 0.6278(3) 0.0244(9) Uani 1 1 d . . . . .
N3B N 0.5709(4) 0.3466(3) 0.4797(3) 0.0238(9) Uani 1 1 d . . . . .
N4B N 0.4410(3) 0.0374(3) 0.6208(3) 0.0245(9) Uani 1 1 d . . . . .
H4B H 0.3435 -0.0220 0.5847 0.029 Uiso 1 1 calc R . . . .
N5B N 0.8197(3) 0.4194(3) 0.6163(3) 0.0247(9) Uani 1 1 d . . . . .
H5B H 0.8418 0.4809 0.5789 0.030 Uiso 1 1 calc R . . . .
C1B C 0.4284(4) 0.2540(4) 0.4429(4) 0.0251(11) Uani 1 1 d . . . . .
C2B C 0.4874(4) 0.1411(4) 0.5760(3) 0.0228(11) Uani 1 1 d . . . . .
C3B C 0.6724(4) 0.3292(4) 0.5741(3) 0.0223(11) Uani 1 1 d . . . . .
C4B C 0.5411(4) 0.0168(4) 0.7248(3) 0.0265(11) Uani 1 1 d . . . . .
H4BA H 0.6457 0.0480 0.7305 0.032 Uiso 1 1 calc R . . . .
H4BB H 0.5040 -0.0861 0.7176 0.032 Uiso 1 1 calc R . . . .
C5B C 0.5497(5) 0.0987(4) 0.8366(4) 0.0374(13) Uani 1 1 d . . . . .
H5BA H 0.5950 0.2023 0.8473 0.045 Uiso 1 1 calc R . . . .
H5BB H 0.4444 0.0733 0.8285 0.045 Uiso 1 1 calc R . . . .
C6B C 0.6445(5) 0.0670(4) 0.9431(4) 0.0421(14) Uani 1 1 d . . . . .
H6BA H 0.5965 -0.0343 0.9352 0.063 Uiso 1 1 calc GR . . . .
H6BB H 0.6503 0.1249 1.0128 0.063 Uiso 1 1 calc GR . . . .
H6BC H 0.7483 0.0900 0.9506 0.063 Uiso 1 1 calc GR . . . .
C7B C 0.9437(4) 0.4224(4) 0.7183(3) 0.0244(11) Uani 1 1 d . . . . .
H7BA H 1.0357 0.4418 0.7049 0.029 Uiso 1 1 calc R . . . .
H7BB H 0.9152 0.3273 0.7307 0.029 Uiso 1 1 calc R . . . .
C8B C 0.9842(5) 0.5344(4) 0.8281(4) 0.0389(14) Uani 1 1 d . . . . .
H8BA H 1.0041 0.6284 0.8138 0.047 Uiso 1 1 calc R . . . .
H8BB H 0.8956 0.5102 0.8460 0.047 Uiso 1 1 calc R . . . .
C9B C 1.1236(5) 0.5441(4) 0.9317(4) 0.0432(15) Uani 1 1 d . . . . .
H9BA H 1.1083 0.4492 0.9414 0.065 Uiso 1 1 calc GR . . . .
H9BB H 1.1386 0.6087 1.0022 0.065 Uiso 1 1 calc GR . . . .
H9BC H 1.2144 0.5808 0.9187 0.065 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1A C1A 1.729(4) . ?
N1A C1A 1.318(4) . ?
N1A C2A 1.364(5) . ?
N2A C2A 1.340(4) . ?
N2A C3A 1.350(4) . ?
N3A C1A 1.316(4) . ?
N3A C3A 1.364(5) . ?
N4A H4A 0.8800 . ?
N4A C2A 1.341(4) . ?
N4A C4A 1.449(5) . ?
N5A H5A 0.8800 . ?
N5A C3A 1.339(4) . ?
N5A C7A 1.441(5) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C4A C5A 1.521(6) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C5A C6A 1.520(6) . ?
C6A H6AA 0.9800 . ?
C6A H6AB 0.9800 . ?
C6A H6AC 0.9800 . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C7A C8A 1.526(6) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8A C9A 1.534(6) . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
Cl1B C1B 1.728(4) . ?
N1B C1B 1.318(4) . ?
N1B C2B 1.358(5) . ?
N2B C2B 1.349(4) . ?
N2B C3B 1.357(4) . ?
N3B C1B 1.322(4) . ?
N3B C3B 1.353(5) . ?
N4B H4B 0.8800 . ?
N4B C2B 1.337(4) . ?
N4B C4B 1.446(5) . ?
N5B H5B 0.8800 . ?
N5B C3B 1.341(4) . ?
N5B C7B 1.435(5) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C4B C5B 1.528(6) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C5B C6B 1.509(6) . ?
C6B H6BA 0.9800 . ?
C6B H6BB 0.9800 . ?
C6B H6BC 0.9800 . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C7B C8B 1.523(6) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C8B C9B 1.509(6) . ?
C9B H9BA 0.9800 . ?
C9B H9BB 0.9800 . ?
C9B H9BC 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A N1A C2A 112.3(3) . . ?
C2A N2A C3A 113.9(3) . . ?
C1A N3A C3A 112.4(3) . . ?
C2A N4A H4A 119.0 . . ?
C2A N4A C4A 121.9(3) . . ?
C4A N4A H4A 119.0 . . ?
C3A N5A H5A 118.8 . . ?
C3A N5A C7A 122.3(3) . . ?
C7A N5A H5A 118.8 . . ?
N1A C1A Cl1A 115.0(3) . . ?
N3A C1A Cl1A 115.2(3) . . ?
N3A C1A N1A 129.8(4) . . ?
N2A C2A N1A 126.0(3) . . ?
N2A C2A N4A 117.7(4) . . ?
N4A C2A N1A 116.3(3) . . ?
N2A C3A N3A 125.6(3) . . ?
N5A C3A N2A 118.1(4) . . ?
N5A C3A N3A 116.3(3) . . ?
N4A C4A H4AA 108.7 . . ?
N4A C4A H4AB 108.7 . . ?
N4A C4A C5A 114.1(4) . . ?
H4AA C4A H4AB 107.6 . . ?
C5A C4A H4AA 108.7 . . ?
C5A C4A H4AB 108.7 . . ?
C4A C5A H5AA 108.5 . . ?
C4A C5A H5AB 108.5 . . ?
H5AA C5A H5AB 107.5 . . ?
C6A C5A C4A 115.2(3) . . ?
C6A C5A H5AA 108.5 . . ?
C6A C5A H5AB 108.5 . . ?
C5A C6A H6AA 109.5 . . ?
C5A C6A H6AB 109.5 . . ?
C5A C6A H6AC 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
N5A C7A H7AA 108.8 . . ?
N5A C7A H7AB 108.8 . . ?
N5A C7A C8A 113.9(4) . . ?
H7AA C7A H7AB 107.7 . . ?
C8A C7A H7AA 108.8 . . ?
C8A C7A H7AB 108.8 . . ?
C7A C8A H8AA 108.7 . . ?
C7A C8A H8AB 108.7 . . ?
C7A C8A C9A 114.3(3) . . ?
H8AA C8A H8AB 107.6 . . ?
C9A C8A H8AA 108.7 . . ?
C9A C8A H8AB 108.7 . . ?
C8A C9A H9AA 109.5 . . ?
C8A C9A H9AB 109.5 . . ?
C8A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C1B N1B C2B 112.5(3) . . ?
C2B N2B C3B 113.8(3) . . ?
C1B N3B C3B 112.3(3) . . ?
C2B N4B H4B 118.0 . . ?
C2B N4B C4B 124.0(3) . . ?
C4B N4B H4B 118.0 . . ?
C3B N5B H5B 117.8 . . ?
C3B N5B C7B 124.4(3) . . ?
C7B N5B H5B 117.8 . . ?
N1B C1B Cl1B 115.2(3) . . ?
N1B C1B N3B 129.8(4) . . ?
N3B C1B Cl1B 114.9(3) . . ?
N2B C2B N1B 125.7(3) . . ?
N4B C2B N1B 115.6(3) . . ?
N4B C2B N2B 118.7(4) . . ?
N3B C3B N2B 125.8(3) . . ?
N5B C3B N2B 118.5(4) . . ?
N5B C3B N3B 115.7(3) . . ?
N4B C4B H4BA 108.9 . . ?
N4B C4B H4BB 108.9 . . ?
N4B C4B C5B 113.2(4) . . ?
H4BA C4B H4BB 107.8 . . ?
C5B C4B H4BA 108.9 . . ?
C5B C4B H4BB 108.9 . . ?
C4B C5B H5BA 109.1 . . ?
C4B C5B H5BB 109.1 . . ?
H5BA C5B H5BB 107.8 . . ?
C6B C5B C4B 112.5(4) . . ?
C6B C5B H5BA 109.1 . . ?
C6B C5B H5BB 109.1 . . ?
C5B C6B H6BA 109.5 . . ?
C5B C6B H6BB 109.5 . . ?
C5B C6B H6BC 109.5 . . ?
H6BA C6B H6BB 109.5 . . ?
H6BA C6B H6BC 109.5 . . ?
H6BB C6B H6BC 109.5 . . ?
N5B C7B H7BA 109.0 . . ?
N5B C7B H7BB 109.0 . . ?
N5B C7B C8B 113.1(4) . . ?
H7BA C7B H7BB 107.8 . . ?
C8B C7B H7BA 109.0 . . ?
C8B C7B H7BB 109.0 . . ?
C7B C8B H8BA 109.2 . . ?
C7B C8B H8BB 109.2 . . ?
H8BA C8B H8BB 107.9 . . ?
C9B C8B C7B 112.0(4) . . ?
C9B C8B H8BA 109.2 . . ?
C9B C8B H8BB 109.2 . . ?
C8B C9B H9BA 109.5 . . ?
C8B C9B H9BB 109.5 . . ?
C8B C9B H9BC 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?

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
N4A C4A C5A C6A -62.1(4) . . . . ?
N5A C7A C8A C9A 61.3(4) . . . . ?
C1A N1A C2A N2A -0.9(6) . . . . ?
C1A N1A C2A N4A 179.9(4) . . . . ?
C1A N3A C3A N2A -0.5(6) . . . . ?
C1A N3A C3A N5A 178.9(4) . . . . ?
C2A N1A C1A Cl1A -179.5(3) . . . . ?
C2A N1A C1A N3A 0.7(7) . . . . ?
C2A N2A C3A N3A 0.4(6) . . . . ?
C2A N2A C3A N5A -179.0(4) . . . . ?
C2A N4A C4A C5A -80.3(5) . . . . ?
C3A N2A C2A N1A 0.3(7) . . . . ?
C3A N2A C2A N4A 179.6(4) . . . . ?
C3A N3A C1A Cl1A -179.9(3) . . . . ?
C3A N3A C1A N1A -0.1(7) . . . . ?
C3A N5A C7A C8A 81.9(5) . . . . ?
C4A N4A C2A N1A -178.4(4) . . . . ?
C4A N4A C2A N2A 2.3(6) . . . . ?
C7A N5A C3A N2A -0.4(6) . . . . ?
C7A N5A C3A N3A -179.9(4) . . . . ?
N4B C4B C5B C6B 175.5(3) . . . . ?
N5B C7B C8B C9B -175.0(3) . . . . ?
C1B N1B C2B N2B 0.5(7) . . . . ?
C1B N1B C2B N4B 179.2(4) . . . . ?
C1B N3B C3B N2B 0.2(6) . . . . ?
C1B N3B C3B N5B 179.9(4) . . . . ?
C2B N1B C1B Cl1B -177.9(3) . . . . ?
C2B N1B C1B N3B 2.3(7) . . . . ?
C2B N2B C3B N3B 2.0(6) . . . . ?
C2B N2B C3B N5B -177.7(4) . . . . ?
C2B N4B C4B C5B 89.9(5) . . . . ?
C3B N2B C2B N1B -2.4(7) . . . . ?
C3B N2B C2B N4B 178.9(4) . . . . ?
C3B N3B C1B Cl1B 177.6(3) . . . . ?
C3B N3B C1B N1B -2.6(7) . . . . ?
C3B N5B C7B C8B -96.5(5) . . . . ?
C4B N4B C2B N1B -176.4(4) . . . . ?
C4B N4B C2B N2B 2.4(7) . . . . ?
C7B N5B C3B N2B -2.9(7) . . . . ?
C7B N5B C3B N3B 177.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT029_fulldata            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.846 Note  
RESPONSE: Data acquisition could not be completed (we tried a couple of 
crystals), as crystals start cracking making it difficult to integrate 
and include the reflections from the last frames.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_partial1_a
_database_code_depnum_ccdc_archive 'CCDC 1552797'
_audit_update_record             
;
2017-06-05 deposited with the CCDC.
2017-07-21 downloaded from the CCDC.
;
_audit_creation_date             2017-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H20 Cl N5'
_chemical_formula_sum            'C11 H20 Cl N5'
_chemical_formula_weight         257.77
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

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

_cell_length_a                   5.0858(6)
_cell_length_b                   10.0093(10)
_cell_length_c                   15.2007(18)
_cell_angle_alpha                104.518(5)
_cell_angle_beta                 92.842(6)
_cell_angle_gamma                100.832(5)
_cell_volume                     731.93(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1316
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      21.577
_cell_measurement_theta_min      2.783
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0999 before and 0.0635 after correction. The Ratio of minimum to maximum transmission is 0.8475. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10068
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.148
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1250
_reflns_number_total             2555
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2555
_refine_ls_number_restraints     131
_refine_ls_R_factor_all          0.1401
_refine_ls_R_factor_gt           0.0678
_refine_ls_restrained_S_all      1.099
_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)+(0.1201P)²+0.1829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2093
_refine_ls_wR_factor_ref         0.2561
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H7C-H11A
 3.826 with sigma of 0.02
 C5-C4 \\sim C5'-C4 \\sim C6'-C5' \\sim C6-C5 \\sim C7-C6 \\sim C7'-C6' \\sim
C9-C8 \\sim C9'-C8 \\sim C9'-
 C10' \\sim C9-C10 \\sim C11-C10 \\sim C11'-C10'
 with sigma of 0.02
 C4-C6 \\sim C5-C7
 with sigma of 0.02
 C4-C6' \\sim C5'-C7'
 with sigma of 0.02
 C8-C10 \\sim C9-C11
 with sigma of 0.02
 C8-C10' \\sim C9'-C11'
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C7) = Uanis(C7')
Uanis(C11) = Uanis(C11')
4. Rigid body (RIGU) restrains
 C4, H4BD, H4BC, H4AB, H4AA, C5, H5A, H5B, C5', H5'A, H5'B, C6, H6B, H6A, C6',
 H6'A, H6'B, C7, H7A, H7B, H7C, C7', H7'A, H7'B, H7'C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C8, H8AB, H8AA, H8BD, H8BC, C9, H9A, H9B, C9', H9'A, H9'B, C10, H10A, H10B,
 C10', H10C, H10D, C11, H11A, H11B, H11C, C11', H11D, H11E, H11F
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: H4BD(0.5) H4BC(0.5) H4AB(0.5) H4AA(0.5) C5(0.5) H5A(0.5) H5B(0.5)
 C5'(0.5) H5'A(0.5) H5'B(0.5) C6(0.5) H6B(0.5) H6A(0.5) C6'(0.5) H6'A(0.5)
 H6'B(0.5) C7(0.5) H7A(0.5) H7B(0.5) H7C(0.5) C7'(0.5) H7'A(0.5) H7'B(0.5)
 H7'C(0.5) H8AB(0.5) H8AA(0.5) H8BD(0.5) H8BC(0.5) C9(0.5) H9A(0.5) H9B(0.5)
 C9'(0.5) H9'A(0.5) H9'B(0.5) C10(0.5) H10A(0.5) H10B(0.5) C10'(0.5) H10C(0.5)
 H10D(0.5) C11(0.5) H11A(0.5) H11B(0.5) H11C(0.5) C11'(0.5) H11D(0.5) H11E(0.5)
 H11F(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C4(H4BD,H4BC), C4(H4AB,H4AA), C5(H5A,H5B), C5'(H5'A,H5'B), C6(H6B,H6A),
 C6'(H6'A,H6'B), C8(H8AB,H8AA), C8(H8BD,H8BC), C9(H9A,H9B), C9'(H9'A,H9'B),
 C10(H10A,H10B), C10'(H10C,H10D)
6.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C7'(H7'A,H7'B,H7'C), C11(H11A,H11B,H11C), C11'(H11D,H11E,H11F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl 0.0180(3) 0.71833(12) 0.63483(9) 0.0880(6) Uani 1 1 d . . . . .
N1 N 0.1293(7) 0.8451(3) 0.5097(2) 0.0664(10) Uani 1 1 d . . . . .
N2 N 0.4135(7) 0.7700(3) 0.3931(2) 0.0688(11) Uani 1 1 d . . . . .
N3 N 0.3257(7) 0.6476(3) 0.5092(3) 0.0690(11) Uani 1 1 d . . . . .
N4 N 0.2281(9) 0.9631(4) 0.3988(3) 0.0744(12) Uani 1 1 d . . . . .
H4 H 0.123(8) 1.007(4) 0.426(2) 0.047(11) Uiso 1 1 d . . . . .
N5 N 0.5927(8) 0.5774(4) 0.3959(3) 0.0744(12) Uani 1 1 d . . . . .
H5 H 0.597(8) 0.521(4) 0.425(3) 0.064(14) Uiso 1 1 d . . . . .
C1 C 0.1765(9) 0.7398(4) 0.5397(3) 0.0647(12) Uani 1 1 d . . . . .
C2 C 0.2588(9) 0.8560(4) 0.4348(3) 0.0658(12) Uani 1 1 d . . . . .
C3 C 0.4411(9) 0.6678(4) 0.4334(3) 0.0648(12) Uani 1 1 d . . . . .
C4 C 0.3441(11) 0.9879(5) 0.3192(3) 0.0797(14) Uani 1 1 d D U . . .
H4BD H 0.5195 0.9586 0.3160 0.096 Uiso 0.5 1 calc R U P A 2
H4BC H 0.3764 1.0900 0.3232 0.096 Uiso 0.5 1 calc R U P A 2
H4AB H 0.5273 0.9678 0.3214 0.096 Uiso 0.5 1 calc R U P B 1
H4AA H 0.3648 1.0897 0.3234 0.096 Uiso 0.5 1 calc R U P B 1
C5 C 0.200(6) 0.908(3) 0.2275(9) 0.143(10) Uani 0.5 1 d D U P C 1
H5A H 0.0097 0.9167 0.2254 0.172 Uiso 0.5 1 calc R U P C 1
H5B H 0.2048 0.8063 0.2165 0.172 Uiso 0.5 1 calc R U P C 1
C5' C 0.162(5) 0.908(2) 0.2350(8) 0.089(5) Uani 0.5 1 d D U P C 2
H5'A H -0.0081 0.9421 0.2369 0.107 Uiso 0.5 1 calc R U P C 2
H5'B H 0.1191 0.8068 0.2342 0.107 Uiso 0.5 1 calc R U P C 2
C6 C 0.339(10) 0.967(5) 0.153(2) 0.248(19) Uani 0.5 1 d D U P C 1
H6B H 0.3541 1.0702 0.1675 0.297 Uiso 0.5 1 calc R U P C 1
H6A H 0.5222 0.9470 0.1494 0.297 Uiso 0.5 1 calc R U P C 1
C6' C 0.285(6) 0.922(3) 0.1463(14) 0.140(7) Uani 0.5 1 d D U P C 2
H6'A H 0.3016 1.0199 0.1416 0.168 Uiso 0.5 1 calc R U P C 2
H6'B H 0.4679 0.9009 0.1478 0.168 Uiso 0.5 1 calc R U P C 2
C7 C 0.172(12) 0.897(5) 0.063(2) 0.339(17) Uani 0.5 1 d D U P C 1
H7A H 0.1344 0.9699 0.0341 0.508 Uiso 0.5 1 calc GR U P C 1
H7B H 0.0026 0.8412 0.0732 0.508 Uiso 0.5 1 calc GR U P C 1
H7C H 0.2712 0.8359 0.0230 0.508 Uiso 0.5 1 calc DGR U P C 1
C7' C 0.108(12) 0.820(5) 0.063(2) 0.339(17) Uani 0.5 1 d D U P C 2
H7'A H -0.0803 0.8260 0.0689 0.508 Uiso 0.5 1 calc GR U P C 2
H7'B H 0.1290 0.7233 0.0595 0.508 Uiso 0.5 1 calc GR U P C 2
H7'C H 0.1633 0.8452 0.0075 0.508 Uiso 0.5 1 calc GR U P C 2
C8 C 0.7191(11) 0.5806(5) 0.3143(3) 0.0832(15) Uani 1 1 d D U . . .
H8AB H 0.8589 0.5232 0.3109 0.100 Uiso 0.5 1 calc R U P D 1
H8AA H 0.8125 0.6790 0.3201 0.100 Uiso 0.5 1 calc R U P D 1
H8BD H 0.8985 0.5566 0.3193 0.100 Uiso 0.5 1 calc R U P E 2
H8BC H 0.7428 0.6761 0.3045 0.100 Uiso 0.5 1 calc R U P E 2
C9 C 0.540(4) 0.4736(17) 0.2350(8) 0.122(6) Uani 0.5 1 d D U P F 2
H9A H 0.5383 0.3774 0.2413 0.146 Uiso 0.5 1 calc R U P F 2
H9B H 0.3540 0.4893 0.2367 0.146 Uiso 0.5 1 calc R U P F 2
C9' C 0.540(5) 0.5286(16) 0.2239(10) 0.135(6) Uani 0.5 1 d D U P F 1
H9'A H 0.3738 0.5665 0.2307 0.162 Uiso 0.5 1 calc R U P F 1
H9'B H 0.6356 0.5638 0.1763 0.162 Uiso 0.5 1 calc R U P F 1
C10 C 0.637(4) 0.4848(19) 0.1451(9) 0.170(6) Uani 0.5 1 d D U P F 2
H10A H 0.6866 0.5856 0.1459 0.204 Uiso 0.5 1 calc R U P F 2
H10B H 0.8005 0.4447 0.1367 0.204 Uiso 0.5 1 calc R U P F 2
C10' C 0.470(6) 0.3734(16) 0.1953(16) 0.263(15) Uani 0.5 1 d D U P F 1
H10C H 0.3477 0.3385 0.2371 0.316 Uiso 0.5 1 calc R U P F 1
H10D H 0.6346 0.3349 0.1982 0.316 Uiso 0.5 1 calc R U P F 1
C11 C 0.430(7) 0.410(3) 0.0661(15) 0.280(11) Uani 0.5 1 d D U P F 2
H11A H 0.4042 0.4745 0.0292 0.420 Uiso 0.5 1 calc DGR U P F 2
H11B H 0.2599 0.3766 0.0888 0.420 Uiso 0.5 1 calc GR U P F 2
H11C H 0.4919 0.3289 0.0285 0.420 Uiso 0.5 1 calc GR U P F 2
C11' C 0.332(8) 0.324(3) 0.0980(16) 0.280(11) Uani 0.5 1 d D U P F 1
H11D H 0.2659 0.4018 0.0824 0.420 Uiso 0.5 1 calc GR U P F 1
H11E H 0.1804 0.2451 0.0935 0.420 Uiso 0.5 1 calc GR U P F 1
H11F H 0.4611 0.2930 0.0556 0.420 Uiso 0.5 1 calc GR U P F 1


_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
Cl C1 1.731(4) . ?
N1 C1 1.305(5) . ?
N1 C2 1.361(5) . ?
N2 C2 1.339(5) . ?
N2 C3 1.342(5) . ?
N3 C1 1.313(5) . ?
N3 C3 1.361(5) . ?
N4 H4 0.82(4) . ?
N4 C2 1.349(5) . ?
N4 C4 1.428(6) . ?
N5 H5 0.80(4) . ?
N5 C3 1.336(5) . ?
N5 C8 1.430(6) . ?
C4 H4BD 0.9900 . ?
C4 H4BC 0.9900 . ?
C4 H4AB 0.9900 . ?
C4 H4AA 0.9900 . ?
C4 C5 1.497(12) . ?
C4 C5' 1.492(11) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.549(14) . ?
C5' H5'A 0.9900 . ?
C5' H5'B 0.9900 . ?
C5' C6' 1.540(13) . ?
C6 H6B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 C7 1.500(14) . ?
C6' H6'A 0.9900 . ?
C6' H6'B 0.9900 . ?
C6' C7' 1.532(13) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7' H7'A 0.9800 . ?
C7' H7'B 0.9800 . ?
C7' H7'C 0.9800 . ?
C8 H8AB 0.9900 . ?
C8 H8AA 0.9900 . ?
C8 H8BD 0.9900 . ?
C8 H8BC 0.9900 . ?
C8 C9 1.518(11) . ?
C8 C9' 1.525(12) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.497(14) . ?
C9' H9'A 0.9900 . ?
C9' H9'B 0.9900 . ?
C9' C10' 1.472(14) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.495(13) . ?
C10' H10C 0.9900 . ?
C10' H10D 0.9900 . ?
C10' C11' 1.524(13) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11' H11D 0.9800 . ?
C11' H11E 0.9800 . ?
C11' H11F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 112.0(3) . . ?
C2 N2 C3 113.9(4) . . ?
C1 N3 C3 112.3(3) . . ?
C2 N4 H4 110(3) . . ?
C2 N4 C4 124.5(4) . . ?
C4 N4 H4 125(3) . . ?
C3 N5 H5 110(3) . . ?
C3 N5 C8 124.0(4) . . ?
C8 N5 H5 126(3) . . ?
N1 C1 Cl 114.9(3) . . ?
N1 C1 N3 130.3(4) . . ?
N3 C1 Cl 114.9(3) . . ?
N2 C2 N1 126.1(4) . . ?
N2 C2 N4 116.8(5) . . ?
N4 C2 N1 117.1(4) . . ?
N2 C3 N3 125.5(4) . . ?
N5 C3 N2 117.5(4) . . ?
N5 C3 N3 117.0(4) . . ?
N4 C4 H4BD 109.5 . . ?
N4 C4 H4BC 109.5 . . ?
N4 C4 H4AB 107.7 . . ?
N4 C4 H4AA 107.7 . . ?
N4 C4 C5 118.4(10) . . ?
N4 C4 C5' 110.7(9) . . ?
H4BD C4 H4BC 108.1 . . ?
H4AB C4 H4AA 107.1 . . ?
C5 C4 H4AB 107.7 . . ?
C5 C4 H4AA 107.7 . . ?
C5' C4 H4BD 109.5 . . ?
C5' C4 H4BC 109.5 . . ?
C4 C5 H5A 109.8 . . ?
C4 C5 H5B 109.8 . . ?
C4 C5 C6 109.3(19) . . ?
H5A C5 H5B 108.3 . . ?
C6 C5 H5A 109.8 . . ?
C6 C5 H5B 109.8 . . ?
C4 C5' H5'A 108.9 . . ?
C4 C5' H5'B 108.9 . . ?
C4 C5' C6' 113.2(16) . . ?
H5'A C5' H5'B 107.7 . . ?
C6' C5' H5'A 108.9 . . ?
C6' C5' H5'B 108.9 . . ?
C5 C6 H6B 110.0 . . ?
C5 C6 H6A 110.0 . . ?
H6B C6 H6A 108.4 . . ?
C7 C6 C5 108(2) . . ?
C7 C6 H6B 110.0 . . ?
C7 C6 H6A 110.0 . . ?
C5' C6' H6'A 109.6 . . ?
C5' C6' H6'B 109.6 . . ?
H6'A C6' H6'B 108.1 . . ?
C7' C6' C5' 110.4(17) . . ?
C7' C6' H6'A 109.6 . . ?
C7' C6' H6'B 109.6 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6' C7' H7'A 109.5 . . ?
C6' C7' H7'B 109.5 . . ?
C6' C7' H7'C 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
N5 C8 H8AB 107.9 . . ?
N5 C8 H8AA 107.9 . . ?
N5 C8 H8BD 110.1 . . ?
N5 C8 H8BC 110.1 . . ?
N5 C8 C9 108.0(8) . . ?
N5 C8 C9' 117.5(10) . . ?
H8AB C8 H8AA 107.2 . . ?
H8BD C8 H8BC 108.4 . . ?
C9 C8 H8BD 110.1 . . ?
C9 C8 H8BC 110.1 . . ?
C9' C8 H8AB 107.9 . . ?
C9' C8 H8AA 107.9 . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 111.5(13) . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9' H9'A 109.5 . . ?
C8 C9' H9'B 109.5 . . ?
H9'A C9' H9'B 108.1 . . ?
C10' C9' C8 110.7(15) . . ?
C10' C9' H9'A 109.5 . . ?
C10' C9' H9'B 109.5 . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 C9 112.8(15) . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C9' C10' H10C 109.7 . . ?
C9' C10' H10D 109.7 . . ?
C9' C10' C11' 109.6(15) . . ?
H10C C10' H10D 108.2 . . ?
C11' C10' H10C 109.7 . . ?
C11' C10' H10D 109.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10' C11' H11D 109.5 . . ?
C10' C11' H11E 109.5 . . ?
C10' C11' H11F 109.5 . . ?
H11D C11' H11E 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?

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
N4 C4 C5 C6 172(2) . . . . ?
N4 C4 C5' C6' -175.9(14) . . . . ?
N5 C8 C9 C10 171.6(13) . . . . ?
N5 C8 C9' C10' -77(2) . . . . ?
C1 N1 C2 N2 1.4(7) . . . . ?
C1 N1 C2 N4 -178.9(4) . . . . ?
C1 N3 C3 N2 0.8(7) . . . . ?
C1 N3 C3 N5 -178.6(4) . . . . ?
C2 N1 C1 Cl -179.8(3) . . . . ?
C2 N1 C1 N3 0.3(7) . . . . ?
C2 N2 C3 N3 0.5(7) . . . . ?
C2 N2 C3 N5 180.0(4) . . . . ?
C2 N4 C4 C5 83.3(18) . . . . ?
C2 N4 C4 C5' 87.9(12) . . . . ?
C3 N2 C2 N1 -1.8(7) . . . . ?
C3 N2 C2 N4 178.5(4) . . . . ?
C3 N3 C1 Cl 178.8(3) . . . . ?
C3 N3 C1 N1 -1.3(7) . . . . ?
C3 N5 C8 C9 -97.2(10) . . . . ?
C3 N5 C8 C9' -74.0(9) . . . . ?
C4 N4 C2 N1 -178.4(4) . . . . ?
C4 N4 C2 N2 1.4(7) . . . . ?
C4 C5 C6 C7 -173(4) . . . . ?
C4 C5' C6' C7' 171(3) . . . . ?
C8 N5 C3 N2 -2.0(7) . . . . ?
C8 N5 C3 N3 177.4(4) . . . . ?
C8 C9 C10 C11 -164.8(19) . . . . ?
C8 C9' C10' C11' -171(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_vina_23nov16_bisbutyl_rt_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1552798'
_audit_update_record             
;
2017-05-29 deposited with the CCDC.
2017-07-21 downloaded from the CCDC.
;
_audit_creation_date             2017-05-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H11 Cl N5, C4 H7'
_chemical_formula_sum            'C11 H18 Cl N5'
_chemical_formula_weight         255.75
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

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

_cell_length_a                   5.0839(11)
_cell_length_b                   10.0172(19)
_cell_length_c                   15.237(3)
_cell_angle_alpha                104.473(14)
_cell_angle_beta                 92.935(15)
_cell_angle_gamma                100.729(13)
_cell_volume                     734.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2829
_cell_measurement_temperature    149.99
_cell_measurement_theta_max      20.113
_cell_measurement_theta_min      2.226
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1458 before and 0.0891 after correction. The Ratio of minimum to maximum transmission is 0.7482. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1032
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19800
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         2.847
_diffrn_ambient_temperature      149.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1375
_reflns_number_total             2726
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2726
_refine_ls_number_restraints     197
_refine_ls_R_factor_all          0.1704
_refine_ls_R_factor_gt           0.1013
_refine_ls_restrained_S_all      1.054
_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)+(0.1535P)²+0.9640P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2822
_refine_ls_wR_factor_ref         0.3429
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H7'B-H11A
 3.18 with sigma of 0.02
 C5'-C4' \\sim C4-C5 \\sim C6-C5 \\sim C6'-C5' \\sim C6'-C7' \\sim C6-C7 \\sim
C10-C11 \\sim C10'-C11' ~
 C10'-C9' \\sim C10-C9 \\sim C9'-C8' \\sim C9-C8
 with sigma of 0.02
 N5'-C8' \\sim N4-C4
 with sigma of 0.02
 N1-C1 \\sim N3-C1
 with sigma of 0.02
 N1-C2 \\sim N3-C3
 with sigma of 0.02
 N2-C2 \\sim N2-C3
 with sigma of 0.02
 N5'-C3 \\sim N4-C2
 with sigma of 0.02
3. Restrained planarity
 C2, N1, N3, C3, N2
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C7) = Uanis(C7')
Uanis(C6) = Uanis(C6')
Uanis(C10) = Uanis(C11)
Uanis(C11) = Uanis(C11')
5. Rigid body (RIGU) restrains
 C4', C5', C6', C7', C7, C5, C4, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C8', C9', C10', C11', C9, C8, C10, C11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C11, C10
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N2, N5', H5', Cl1, N4, H4, N3, N1, C3, C1, C2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: C4'(0.5) C5'(0.5) H5'A(0.5) H5'B(0.5) C6'(0.5) H6'A(0.5) H6'B(0.5)
 C7'(0.5) H7'A(0.5) H7'B(0.5) H7'C(0.5) C8'(0.5) C9'(0.5) H9'A(0.5) H9'B(0.5)
 C10'(0.5) H10C(0.5) H10D(0.5) C11'(0.5) H11D(0.5) H11E(0.5) H11F(0.5) C7(0.5)
 H7A(0.5) H7B(0.5) H7C(0.5) C5(0.5) H5A(0.5) H5B(0.5) C4(0.5) H4A(0.5) H4B(0.5)
 C9(0.5) H9A(0.5) H9B(0.5) C6(0.5) H6A(0.5) H6B(0.5) C8(0.5) H8A(0.5) H8B(0.5)
 C10(0.5) H10A(0.5) H10B(0.5) C11(0.5) H11A(0.5) H11B(0.5) H11C(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C5'(H5'A,H5'B), C6'(H6'A,H6'B), C9'(H9'A,H9'B), C10'(H10C,H10D), C5(H5A,H5B),
 C4(H4A,H4B), C9(H9A,H9B), C6(H6A,H6B), C8(H8A,H8B), C10(H10A,H10B)
7.b Aromatic/amide H refined with riding coordinates:
 N5'(H5'), N4(H4)
7.c Idealised Me refined as rotating group:
 C7'(H7'A,H7'B,H7'C), C11'(H11D,H11E,H11F), C7(H7A,H7B,H7C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.5894(9) 0.2315(4) 0.6075(3) 0.0687(14) Uani 1 1 d D U . . .
N5' N 0.7759(10) 0.0369(5) 0.6006(3) 0.0720(15) Uani 1 1 d D U . A 1
H5' H 0.8670 -0.0224 0.5698 0.086 Uiso 1 1 calc R U . A 1
C4' C 0.310(6) 0.426(3) 0.698(2) 0.095(9) Uani 0.5 1 d D U P B 2
C5' C 0.502(9) 0.535(5) 0.777(2) 0.194(15) Uani 0.5 1 d D U P B 2
H5'A H 0.6908 0.5224 0.7767 0.233 Uiso 0.5 1 calc R . P B 2
H5'B H 0.4937 0.6334 0.7796 0.233 Uiso 0.5 1 calc R . P B 2
C6' C 0.363(10) 0.484(5) 0.8527(19) 0.258(13) Uani 0.5 1 d D U P B 2
H6'A H 0.3796 0.3867 0.8505 0.309 Uiso 0.5 1 calc R . P B 2
H6'B H 0.1699 0.4888 0.8484 0.309 Uiso 0.5 1 calc R . P B 2
C7' C 0.518(9) 0.590(6) 0.940(2) 0.312(16) Uani 0.5 1 d D U P B 2
H7'A H 0.6846 0.6412 0.9242 0.468 Uiso 0.5 1 calc GR . P B 2
H7'B H 0.5604 0.5384 0.9837 0.468 Uiso 0.5 1 calc DGR . P B 2
H7'C H 0.4060 0.6562 0.9662 0.468 Uiso 0.5 1 calc GR . P B 2
C8' C 0.637(5) 0.017(2) 0.6763(15) 0.060(5) Uani 0.5 1 d D U P C 2
C9' C 0.824(6) 0.092(2) 0.7633(12) 0.082(5) Uani 0.5 1 d D U P C 2
H9'A H 0.8757 0.1941 0.7666 0.098 Uiso 0.5 1 calc R . P C 2
H9'B H 0.9903 0.0541 0.7617 0.098 Uiso 0.5 1 calc R . P C 2
C10' C 0.688(6) 0.074(3) 0.8478(13) 0.135(8) Uani 0.5 1 d D U P C 2
H10C H 0.5843 0.1498 0.8650 0.161 Uiso 0.5 1 calc R . P C 2
H10D H 0.5554 -0.0163 0.8299 0.161 Uiso 0.5 1 calc R . P C 2
C11' C 0.860(9) 0.076(5) 0.933(2) 0.274(12) Uani 0.5 1 d D U P C 2
H11D H 0.9279 0.1733 0.9687 0.411 Uiso 0.5 1 calc GR . P C 2
H11E H 1.0112 0.0307 0.9154 0.411 Uiso 0.5 1 calc GR . P C 2
H11F H 0.7502 0.0241 0.9698 0.411 Uiso 0.5 1 calc GR . P C 2
Cl1 Cl 0.9795(4) 0.28099(17) 0.36507(12) 0.0880(8) Uani 1 1 d . U . A 1
N4 N 0.4099(10) 0.4240(5) 0.6032(4) 0.0731(15) Uani 1 1 d D U . A 1
H4 H 0.4013 0.4937 0.5783 0.088 Uiso 1 1 calc R U . A 1
N3 N 0.8690(9) 0.1537(4) 0.4903(3) 0.0631(13) Uani 1 1 d D U . A 1
N1 N 0.6737(9) 0.3519(4) 0.4904(3) 0.0668(13) Uani 1 1 d D U . A 1
C7 C 0.671(9) 0.634(7) 0.907(2) 0.312(16) Uani 0.5 1 d D U P A 1
H7A H 0.6613 0.6723 0.9720 0.468 Uiso 0.5 1 calc GR . P A 1
H7B H 0.7514 0.7105 0.8806 0.468 Uiso 0.5 1 calc GR . P A 1
H7C H 0.7831 0.5629 0.8980 0.468 Uiso 0.5 1 calc GR . P A 1
C5 C 0.454(7) 0.497(3) 0.7653(14) 0.138(10) Uani 0.5 1 d D U P A 1
H5A H 0.5633 0.4290 0.7752 0.165 Uiso 0.5 1 calc R . P A 1
H5B H 0.5780 0.5718 0.7474 0.165 Uiso 0.5 1 calc R . P A 1
C4 C 0.264(5) 0.418(2) 0.6789(14) 0.056(5) Uani 0.5 1 d D U P A 1
H4A H 0.1971 0.3192 0.6793 0.068 Uiso 0.5 1 calc R . P A 1
H4B H 0.1072 0.4634 0.6758 0.068 Uiso 0.5 1 calc R . P A 1
C9 C 0.830(10) 0.092(4) 0.779(2) 0.171(13) Uani 0.5 1 d D U P A 1
H9A H 0.8126 0.1914 0.7904 0.206 Uiso 0.5 1 calc R . P A 1
H9B H 1.0230 0.0885 0.7784 0.206 Uiso 0.5 1 calc R . P A 1
C6 C 0.387(9) 0.567(5) 0.8590(19) 0.258(13) Uani 0.5 1 d D U P A 1
H6A H 0.2919 0.4968 0.8886 0.309 Uiso 0.5 1 calc R . P A 1
H6B H 0.2782 0.6382 0.8571 0.309 Uiso 0.5 1 calc R . P A 1
C3 C 0.7431(11) 0.1434(5) 0.5656(4) 0.0642(15) Uani 1 1 d D U . A 1
C8 C 0.677(6) 0.006(3) 0.6857(19) 0.096(9) Uani 0.5 1 d D U P A 1
H8A H 0.6736 -0.0944 0.6808 0.115 Uiso 0.5 1 calc R . P A 1
H8B H 0.4885 0.0188 0.6867 0.115 Uiso 0.5 1 calc R . P A 1
C1 C 0.8223(11) 0.2602(5) 0.4600(4) 0.0641(15) Uani 1 1 d D U . A 1
C10 C 0.708(10) 0.027(4) 0.853(2) 0.235(18) Uani 0.5 1 d D U P A 1
H10A H 0.5092 -0.0012 0.8442 0.282 Uiso 0.5 1 calc R . P A 1
H10B H 0.7897 -0.0505 0.8635 0.282 Uiso 0.5 1 calc R . P A 1
C2 C 0.5603(11) 0.3329(5) 0.5658(4) 0.0652(15) Uani 1 1 d D U . A 1
C11 C 0.810(10) 0.167(4) 0.926(2) 0.274(12) Uani 0.5 1 d D U P A 1
H11A H 0.7024 0.2355 0.9181 0.411 Uiso 0.5 1 calc DGR . P A 1
H11B H 0.9993 0.2035 0.9200 0.411 Uiso 0.5 1 calc GR . P A 1
H11C H 0.7947 0.1516 0.9868 0.411 Uiso 0.5 1 calc GR . P A 1


_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
N2 C3 1.350(6) . ?
N2 C2 1.351(6) . ?
N5' H5' 0.8800 . ?
N5' C3 1.338(6) . ?
N5' C8 1.50(3) . ?
C4' C5' 1.562(16) . ?
C5' H5'A 0.9900 . ?
C5' H5'B 0.9900 . ?
C5' C6' 1.519(17) . ?
C6' H6'A 0.9900 . ?
C6' H6'B 0.9900 . ?
C6' C7' 1.540(17) . ?
C7' H7'A 0.9800 . ?
C7' H7'B 0.9800 . ?
C7' H7'C 0.9800 . ?
C8' C9' 1.528(14) . ?
C9' H9'A 0.9900 . ?
C9' H9'B 0.9900 . ?
C9' C10' 1.528(15) . ?
C10' H10C 0.9900 . ?
C10' H10D 0.9900 . ?
C10' C11' 1.523(17) . ?
C11' H11D 0.9800 . ?
C11' H11E 0.9800 . ?
C11' H11F 0.9800 . ?
Cl1 C1 1.727(6) . ?
N4 H4 0.8800 . ?
N4 C4 1.41(2) . ?
N4 C2 1.336(6) . ?
N3 C3 1.359(7) . ?
N3 C1 1.318(5) . ?
N1 C1 1.308(6) . ?
N1 C2 1.352(7) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 C6 1.535(17) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C4 1.534(14) . ?
C5 C6 1.509(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.539(15) . ?
C9 C10 1.546(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.533(17) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N2 C2 113.9(5) . . ?
C3 N5' H5' 116.0 . . ?
C3 N5' C8 128.1(12) . . ?
C8 N5' H5' 116.0 . . ?
C4' C5' H5'A 112.7 . . ?
C4' C5' H5'B 112.7 . . ?
H5'A C5' H5'B 110.2 . . ?
C6' C5' C4' 95(2) . . ?
C6' C5' H5'A 112.7 . . ?
C6' C5' H5'B 112.7 . . ?
C5' C6' H6'A 111.3 . . ?
C5' C6' H6'B 111.3 . . ?
C5' C6' C7' 103(3) . . ?
H6'A C6' H6'B 109.2 . . ?
C7' C6' H6'A 111.3 . . ?
C7' C6' H6'B 111.3 . . ?
C6' C7' H7'A 109.5 . . ?
C6' C7' H7'B 109.5 . . ?
C6' C7' H7'C 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
C8' C9' H9'A 109.4 . . ?
C8' C9' H9'B 109.4 . . ?
C8' C9' C10' 111.1(17) . . ?
H9'A C9' H9'B 108.0 . . ?
C10' C9' H9'A 109.4 . . ?
C10' C9' H9'B 109.4 . . ?
C9' C10' H10C 107.5 . . ?
C9' C10' H10D 107.5 . . ?
H10C C10' H10D 107.0 . . ?
C11' C10' C9' 119(3) . . ?
C11' C10' H10C 107.5 . . ?
C11' C10' H10D 107.5 . . ?
C10' C11' H11D 109.5 . . ?
C10' C11' H11E 109.5 . . ?
C10' C11' H11F 109.5 . . ?
H11D C11' H11E 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
C4 N4 H4 117.1 . . ?
C2 N4 H4 117.1 . . ?
C2 N4 C4 125.8(11) . . ?
C1 N3 C3 112.5(4) . . ?
C1 N1 C2 112.6(4) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H5A C5 H5B 105.8 . . ?
C4 C5 H5A 104.9 . . ?
C4 C5 H5B 104.9 . . ?
C6 C5 H5A 104.9 . . ?
C6 C5 H5B 104.9 . . ?
C6 C5 C4 129(3) . . ?
N4 C4 C5 107.8(15) . . ?
N4 C4 H4A 110.1 . . ?
N4 C4 H4B 110.1 . . ?
C5 C4 H4A 110.1 . . ?
C5 C4 H4B 110.1 . . ?
H4A C4 H4B 108.5 . . ?
H9A C9 H9B 108.4 . . ?
C8 C9 H9A 110.0 . . ?
C8 C9 H9B 110.0 . . ?
C8 C9 C10 109(3) . . ?
C10 C9 H9A 110.0 . . ?
C10 C9 H9B 110.0 . . ?
C7 C6 H6A 111.7 . . ?
C7 C6 H6B 111.7 . . ?
C5 C6 C7 100(3) . . ?
C5 C6 H6A 111.7 . . ?
C5 C6 H6B 111.7 . . ?
H6A C6 H6B 109.5 . . ?
N2 C3 N3 125.3(4) . . ?
N5' C3 N2 117.9(5) . . ?
N5' C3 N3 116.8(5) . . ?
N5' C8 C9 119(2) . . ?
N5' C8 H8A 107.5 . . ?
N5' C8 H8B 107.5 . . ?
C9 C8 H8A 107.5 . . ?
C9 C8 H8B 107.5 . . ?
H8A C8 H8B 107.0 . . ?
N3 C1 Cl1 115.0(4) . . ?
N1 C1 Cl1 115.0(4) . . ?
N1 C1 N3 130.0(5) . . ?
C9 C10 H10A 113.4 . . ?
C9 C10 H10B 113.4 . . ?
H10A C10 H10B 110.7 . . ?
C11 C10 C9 91(3) . . ?
C11 C10 H10A 113.4 . . ?
C11 C10 H10B 113.4 . . ?
N2 C2 N1 125.7(5) . . ?
N4 C2 N2 117.3(5) . . ?
N4 C2 N1 117.0(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
C4' C5' C6' C7' -176(4) . . . . ?
C8' C9' C10' C11' 151(3) . . . . ?
C4 N4 C2 N2 -4.5(14) . . . . ?
C4 N4 C2 N1 176.6(12) . . . . ?
C4 C5 C6 C7 -175(4) . . . . ?
C6 C5 C4 N4 156(3) . . . . ?
C3 N2 C2 N4 179.8(5) . . . . ?
C3 N2 C2 N1 -1.4(9) . . . . ?
C3 N5' C8 C9 -78(3) . . . . ?
C3 N3 C1 Cl1 179.3(4) . . . . ?
C3 N3 C1 N1 -1.3(9) . . . . ?
C8 N5' C3 N2 -4.3(18) . . . . ?
C8 N5' C3 N3 175.5(16) . . . . ?
C8 C9 C10 C11 -157(3) . . . . ?
C1 N3 C3 N2 -1.0(9) . . . . ?
C1 N3 C3 N5' 179.1(5) . . . . ?
C1 N1 C2 N2 -0.4(8) . . . . ?
C1 N1 C2 N4 178.4(5) . . . . ?
C10 C9 C8 N5' -173(3) . . . . ?
C2 N2 C3 N5' -178.0(5) . . . . ?
C2 N2 C3 N3 2.2(9) . . . . ?
C2 N4 C4 C5 87(2) . . . . ?
C2 N1 C1 Cl1 -178.6(4) . . . . ?
C2 N1 C1 N3 2.0(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_bm11_a
_database_code_depnum_ccdc_archive 'CCDC 1552800'
_audit_update_record             
;
2017-05-29 deposited with the CCDC.
2017-07-21 downloaded from the CCDC.
;
_audit_creation_date             2017-05-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H12 Cl2 N4'
_chemical_formula_sum            'C8 H12 Cl2 N4'
_chemical_formula_weight         235.12
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.548(5)
_cell_length_b                   5.0000(10)
_cell_length_c                   19.343(4)
_cell_angle_alpha                90
_cell_angle_beta                 115.30(3)
_cell_angle_gamma                90
_cell_volume                     2233.8(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2289
_cell_measurement_temperature    100
_cell_measurement_theta_max      22.5
_cell_measurement_theta_min      2.5
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.549
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 0.939
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12722
_diffrn_reflns_point_group_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         3.294
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.939
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'Australian Synchrotron'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1673
_reflns_number_total             1841
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1841
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0495P)²+3.5860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0963
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.59389(2) 1.09764(12) 0.30459(3) 0.03276(19) Uani 1 1 d . . . . .
Cl2 Cl 0.73788(2) 0.37711(12) 0.29959(3) 0.02824(18) Uani 1 1 d . . . . .
N1 N 0.66805(7) 0.7362(4) 0.30901(9) 0.0253(4) Uani 1 1 d . . . . .
N2 N 0.71638(7) 0.4524(4) 0.41683(9) 0.0202(4) Uani 1 1 d . . . . .
N3 N 0.64859(7) 0.7814(4) 0.41879(10) 0.0235(4) Uani 1 1 d . . . . .
N4 N 0.69687(7) 0.4975(4) 0.52128(9) 0.0233(4) Uani 1 1 d . . . . .
H4 H 0.7240 0.3763 0.5428 0.028 Uiso 1 1 calc R . . . .
C1 C 0.64250(8) 0.8440(5) 0.34989(12) 0.0245(5) Uani 1 1 d . . . . .
C2 C 0.70370(8) 0.5410(4) 0.34759(11) 0.0217(4) Uani 1 1 d . . . . .
C3 C 0.68670(8) 0.5796(4) 0.45162(11) 0.0211(4) Uani 1 1 d . . . . .
C4 C 0.66581(9) 0.5955(5) 0.56481(13) 0.0263(5) Uani 1 1 d . . . . .
H4A H 0.6490 0.7731 0.5449 0.032 Uiso 1 1 calc R . . . .
H4B H 0.6936 0.6178 0.6191 0.032 Uiso 1 1 calc R . . . .
C5 C 0.61776(9) 0.4067(5) 0.56010(12) 0.0258(5) Uani 1 1 d . . . . .
H5A H 0.6345 0.2288 0.5798 0.031 Uiso 1 1 calc R . . . .
H5B H 0.5897 0.3854 0.5060 0.031 Uiso 1 1 calc R . . . .
C6 C 0.58620(9) 0.5111(5) 0.60615(12) 0.0249(5) Uani 1 1 d . . . . .
H6A H 0.6148 0.5412 0.6596 0.030 Uiso 1 1 calc R . . . .
H6B H 0.5682 0.6856 0.5848 0.030 Uiso 1 1 calc R . . . .
C7 C 0.53964(9) 0.3223(5) 0.60597(13) 0.0315(5) Uani 1 1 d . . . . .
H7A H 0.5576 0.1484 0.6280 0.038 Uiso 1 1 calc R . . . .
H7B H 0.5112 0.2904 0.5525 0.038 Uiso 1 1 calc R . . . .
C8 C 0.50806(10) 0.4306(6) 0.65136(15) 0.0376(6) Uani 1 1 d . . . . .
H8A H 0.4914 0.6057 0.6310 0.056 Uiso 1 1 calc GR . . . .
H8B H 0.5354 0.4489 0.7052 0.056 Uiso 1 1 calc GR . . . .
H8C H 0.4771 0.3067 0.6470 0.056 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.729(2) . ?
Cl2 C2 1.729(2) . ?
N1 C1 1.335(3) . ?
N1 C2 1.326(3) . ?
N2 C2 1.313(3) . ?
N2 C3 1.367(3) . ?
N3 C1 1.312(3) . ?
N3 C3 1.357(3) . ?
N4 H4 0.8800 . ?
N4 C3 1.324(3) . ?
N4 C4 1.466(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.520(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.526(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.517(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.523(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 110.85(17) . . ?
C2 N2 C3 113.45(18) . . ?
C1 N3 C3 113.75(18) . . ?
C3 N4 H4 117.9 . . ?
C3 N4 C4 124.18(18) . . ?
C4 N4 H4 117.9 . . ?
N1 C1 Cl1 115.03(16) . . ?
N3 C1 Cl1 115.95(16) . . ?
N3 C1 N1 129.0(2) . . ?
N1 C2 Cl2 115.46(15) . . ?
N2 C2 Cl2 115.24(16) . . ?
N2 C2 N1 129.29(19) . . ?
N3 C3 N2 123.62(18) . . ?
N4 C3 N2 116.60(19) . . ?
N4 C3 N3 119.77(18) . . ?
N4 C4 H4A 109.1 . . ?
N4 C4 H4B 109.1 . . ?
N4 C4 C5 112.30(18) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C4 C5 C6 111.55(18) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C5 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 C5 113.27(19) . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C6 C7 C8 112.7(2) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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
N4 C4 C5 C6 179.62(18) . . . . ?
C1 N1 C2 Cl2 178.00(15) . . . . ?
C1 N1 C2 N2 -1.3(3) . . . . ?
C1 N3 C3 N2 0.2(3) . . . . ?
C1 N3 C3 N4 179.86(19) . . . . ?
C2 N1 C1 Cl1 -178.90(14) . . . . ?
C2 N1 C1 N3 0.0(3) . . . . ?
C2 N2 C3 N3 -1.2(3) . . . . ?
C2 N2 C3 N4 179.14(18) . . . . ?
C3 N2 C2 Cl2 -177.44(14) . . . . ?
C3 N2 C2 N1 1.8(3) . . . . ?
C3 N3 C1 Cl1 179.35(14) . . . . ?
C3 N3 C1 N1 0.5(3) . . . . ?
C3 N4 C4 C5 98.7(3) . . . . ?
C4 N4 C3 N2 -174.98(19) . . . . ?
C4 N4 C3 N3 5.3(3) . . . . ?
C4 C5 C6 C7 -177.36(19) . . . . ?
C5 C6 C7 C8 -179.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT029_bm11_a              
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.939 Note  
RESPONSE: Data acquisition at Australian Synchrotron was carried out on
a one circle goniometer that leaves gaps in covering the reciprocal space,
particulalry for the low symmetry space groups.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_bm10_a
_database_code_depnum_ccdc_archive 'CCDC 1552799'
_audit_update_record             
;
2017-05-29 deposited with the CCDC.
2017-07-21 downloaded from the CCDC.
;
_audit_creation_date             2017-05-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H10 Cl2 N4'
_chemical_formula_sum            'C7 H10 Cl2 N4'
_chemical_formula_weight         221.09
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

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

_cell_length_a                   5.0120(10)
_cell_length_b                   11.794(2)
_cell_length_c                   17.086(3)
_cell_angle_alpha                86.52(3)
_cell_angle_beta                 84.11(3)
_cell_angle_gamma                82.67(3)
_cell_volume                     995.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    597
_cell_measurement_temperature    100
_cell_measurement_theta_max      20.00
_cell_measurement_theta_min      2.26
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.913
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12269
_diffrn_reflns_point_group_measured_fraction_full 0.913
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.743
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.913
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  'Australian Synchrotron'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2979
_reflns_number_total             3181
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0295
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+0.7320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0768
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4B(H4BA,H4BB), C5B(H5BA,H5BB), C6B(H6BA,H6BB), C4A(H4AA,H4AB), C5A(H5AA,
 H5AB), C6A(H6AA,H6AB)
2.b Aromatic/amide H refined with riding coordinates:
 N4B(H4B), N4A(H4A)
2.c Idealised Me refined as rotating group:
 C7B(H7BA,H7BB,H7BC), C7A(H7AA,H7AB,H7AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1B Cl 0.19271(9) 0.63803(4) 0.79279(2) 0.02009(13) Uani 1 1 d . . . . .
Cl2B Cl 0.98921(9) 0.31282(4) 0.80535(3) 0.02243(13) Uani 1 1 d . . . . .
N1B N 0.5838(3) 0.47278(12) 0.80575(9) 0.0183(3) Uani 1 1 d . . . . .
N2B N 0.6108(3) 0.34544(12) 0.91982(9) 0.0174(3) Uani 1 1 d . . . . .
N3B N 0.2434(3) 0.49696(12) 0.91368(8) 0.0158(3) Uani 1 1 d . . . . .
N4B N 0.2706(3) 0.37256(12) 1.02163(8) 0.0170(3) Uani 1 1 d . . . . .
H4B H 0.1270 0.4154 1.0422 0.020 Uiso 1 1 calc R . . . .
C1B C 0.3578(4) 0.52318(14) 0.84345(10) 0.0165(4) Uani 1 1 d . . . . .
C2B C 0.6941(4) 0.38528(14) 0.84934(10) 0.0172(4) Uani 1 1 d . . . . .
C3B C 0.3774(4) 0.40435(14) 0.95107(10) 0.0152(4) Uani 1 1 d . . . . .
C4B C 0.3745(4) 0.27114(14) 1.06787(10) 0.0175(4) Uani 1 1 d . . . . .
H4BA H 0.3499 0.2880 1.1244 0.021 Uiso 1 1 calc R . . . .
H4BB H 0.5707 0.2529 1.0527 0.021 Uiso 1 1 calc R . . . .
C5B C 0.2334(4) 0.16764(14) 1.05582(10) 0.0177(4) Uani 1 1 d . . . . .
H5BA H 0.2710 0.1462 1.0003 0.021 Uiso 1 1 calc R . . . .
H5BB H 0.0357 0.1873 1.0669 0.021 Uiso 1 1 calc R . . . .
C6B C 0.3303(4) 0.06669(16) 1.10986(11) 0.0233(4) Uani 1 1 d . . . . .
H6BA H 0.5295 0.0507 1.1006 0.028 Uiso 1 1 calc R . . . .
H6BB H 0.2850 0.0878 1.1653 0.028 Uiso 1 1 calc R . . . .
C7B C 0.2070(5) -0.04146(17) 1.09774(13) 0.0321(5) Uani 1 1 d . . . . .
H7BA H 0.2469 -0.0619 1.0427 0.048 Uiso 1 1 calc GR . . . .
H7BB H 0.0108 -0.0281 1.1106 0.048 Uiso 1 1 calc GR . . . .
H7BC H 0.2838 -0.1041 1.1321 0.048 Uiso 1 1 calc GR . . . .
Cl1A Cl 1.29813(10) 0.30756(4) 0.36031(3) 0.02505(13) Uani 1 1 d . . . . .
Cl2A Cl 0.71290(10) 0.01410(4) 0.27668(2) 0.02498(13) Uani 1 1 d . . . . .
N1A N 1.0001(3) 0.15774(13) 0.32598(9) 0.0198(3) Uani 1 1 d . . . . .
N2A N 0.7107(3) 0.06436(12) 0.42198(8) 0.0165(3) Uani 1 1 d . . . . .
N3A N 0.9810(3) 0.20206(12) 0.46117(9) 0.0186(3) Uani 1 1 d . . . . .
N4A N 0.6919(3) 0.11057(13) 0.55124(8) 0.0179(3) Uani 1 1 d . . . . .
H4A H 0.5813 0.0581 0.5609 0.021 Uiso 1 1 calc R . . . .
C1A C 1.0686(4) 0.21145(15) 0.38617(11) 0.0185(4) Uani 1 1 d . . . . .
C2A C 0.8203(4) 0.08666(14) 0.35050(10) 0.0175(4) Uani 1 1 d . . . . .
C3A C 0.7977(4) 0.12675(14) 0.47757(10) 0.0165(4) Uani 1 1 d . . . . .
C4A C 0.7472(4) 0.17448(16) 0.61766(10) 0.0208(4) Uani 1 1 d . . . . .
H4AA H 0.9147 0.2103 0.6032 0.025 Uiso 1 1 calc R . . . .
H4AB H 0.7775 0.1206 0.6635 0.025 Uiso 1 1 calc R . . . .
C5A C 0.5160(4) 0.26732(15) 0.64090(10) 0.0198(4) Uani 1 1 d . . . . .
H5AA H 0.3493 0.2308 0.6552 0.024 Uiso 1 1 calc R . . . .
H5AB H 0.5581 0.3031 0.6884 0.024 Uiso 1 1 calc R . . . .
C6A C 0.4609(5) 0.36063(17) 0.57728(11) 0.0272(5) Uani 1 1 d . . . . .
H6AA H 0.6290 0.3953 0.5610 0.033 Uiso 1 1 calc R . . . .
H6AB H 0.4079 0.3260 0.5307 0.033 Uiso 1 1 calc R . . . .
C7A C 0.2393(5) 0.45381(17) 0.60470(13) 0.0322(5) Uani 1 1 d . . . . .
H7AA H 0.2943 0.4907 0.6493 0.048 Uiso 1 1 calc GR . . . .
H7AB H 0.0725 0.4200 0.6211 0.048 Uiso 1 1 calc GR . . . .
H7AC H 0.2081 0.5109 0.5614 0.048 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1B C1B 1.7283(19) . ?
Cl2B C2B 1.7352(19) . ?
N1B C1B 1.333(2) . ?
N1B C2B 1.331(2) . ?
N2B C2B 1.313(2) . ?
N2B C3B 1.358(2) . ?
N3B C1B 1.313(2) . ?
N3B C3B 1.367(2) . ?
N4B H4B 0.8800 . ?
N4B C3B 1.321(2) . ?
N4B C4B 1.462(2) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C4B C5B 1.521(3) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C5B C6B 1.522(2) . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C6B C7B 1.520(3) . ?
C7B H7BA 0.9800 . ?
C7B H7BB 0.9800 . ?
C7B H7BC 0.9800 . ?
Cl1A C1A 1.724(2) . ?
Cl2A C2A 1.7323(19) . ?
N1A C1A 1.336(3) . ?
N1A C2A 1.328(3) . ?
N2A C2A 1.313(2) . ?
N2A C3A 1.373(2) . ?
N3A C1A 1.314(2) . ?
N3A C3A 1.356(2) . ?
N4A H4A 0.8800 . ?
N4A C3A 1.327(2) . ?
N4A C4A 1.468(2) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C4A C5A 1.528(3) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C5A C6A 1.519(3) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C6A C7A 1.518(3) . ?
C7A H7AA 0.9800 . ?
C7A H7AB 0.9800 . ?
C7A H7AC 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2B N1B C1B 110.88(15) . . ?
C2B N2B C3B 113.32(15) . . ?
C1B N3B C3B 113.87(16) . . ?
C3B N4B H4B 117.7 . . ?
C3B N4B C4B 124.53(15) . . ?
C4B N4B H4B 117.7 . . ?
N1B C1B Cl1B 115.56(13) . . ?
N3B C1B Cl1B 115.75(14) . . ?
N3B C1B N1B 128.69(17) . . ?
N1B C2B Cl2B 114.66(13) . . ?
N2B C2B Cl2B 115.77(14) . . ?
N2B C2B N1B 129.57(17) . . ?
N2B C3B N3B 123.66(16) . . ?
N4B C3B N2B 119.47(16) . . ?
N4B C3B N3B 116.87(16) . . ?
N4B C4B H4BA 109.1 . . ?
N4B C4B H4BB 109.1 . . ?
N4B C4B C5B 112.31(15) . . ?
H4BA C4B H4BB 107.9 . . ?
C5B C4B H4BA 109.1 . . ?
C5B C4B H4BB 109.1 . . ?
C4B C5B H5BA 109.5 . . ?
C4B C5B H5BB 109.5 . . ?
C4B C5B C6B 110.77(15) . . ?
H5BA C5B H5BB 108.1 . . ?
C6B C5B H5BA 109.5 . . ?
C6B C5B H5BB 109.5 . . ?
C5B C6B H6BA 108.9 . . ?
C5B C6B H6BB 108.9 . . ?
H6BA C6B H6BB 107.7 . . ?
C7B C6B C5B 113.34(17) . . ?
C7B C6B H6BA 108.9 . . ?
C7B C6B H6BB 108.9 . . ?
C6B C7B H7BA 109.5 . . ?
C6B C7B H7BB 109.5 . . ?
C6B C7B H7BC 109.5 . . ?
H7BA C7B H7BB 109.5 . . ?
H7BA C7B H7BC 109.5 . . ?
H7BB C7B H7BC 109.5 . . ?
C2A N1A C1A 110.99(15) . . ?
C2A N2A C3A 112.91(17) . . ?
C1A N3A C3A 113.81(16) . . ?
C3A N4A H4A 117.8 . . ?
C3A N4A C4A 124.31(17) . . ?
C4A N4A H4A 117.8 . . ?
N1A C1A Cl1A 114.66(14) . . ?
N3A C1A Cl1A 116.60(15) . . ?
N3A C1A N1A 128.74(18) . . ?
N1A C2A Cl2A 114.83(13) . . ?
N2A C2A Cl2A 115.57(15) . . ?
N2A C2A N1A 129.60(17) . . ?
N3A C3A N2A 123.94(16) . . ?
N4A C3A N2A 116.51(17) . . ?
N4A C3A N3A 119.54(16) . . ?
N4A C4A H4AA 109.1 . . ?
N4A C4A H4AB 109.1 . . ?
N4A C4A C5A 112.32(16) . . ?
H4AA C4A H4AB 107.9 . . ?
C5A C4A H4AA 109.1 . . ?
C5A C4A H4AB 109.1 . . ?
C4A C5A H5AA 108.6 . . ?
C4A C5A H5AB 108.6 . . ?
H5AA C5A H5AB 107.6 . . ?
C6A C5A C4A 114.55(16) . . ?
C6A C5A H5AA 108.6 . . ?
C6A C5A H5AB 108.6 . . ?
C5A C6A H6AA 109.1 . . ?
C5A C6A H6AB 109.1 . . ?
H6AA C6A H6AB 107.8 . . ?
C7A C6A C5A 112.47(16) . . ?
C7A C6A H6AA 109.1 . . ?
C7A C6A H6AB 109.1 . . ?
C6A C7A H7AA 109.5 . . ?
C6A C7A H7AB 109.5 . . ?
C6A C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?

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
N4B C4B C5B C6B -175.31(15) . . . . ?
C1B N1B C2B Cl2B 179.60(12) . . . . ?
C1B N1B C2B N2B 0.5(3) . . . . ?
C1B N3B C3B N2B 1.3(3) . . . . ?
C1B N3B C3B N4B -179.13(16) . . . . ?
C2B N1B C1B Cl1B -179.59(12) . . . . ?
C2B N1B C1B N3B 0.1(3) . . . . ?
C2B N2B C3B N3B -0.9(2) . . . . ?
C2B N2B C3B N4B 179.56(16) . . . . ?
C3B N2B C2B Cl2B -179.21(12) . . . . ?
C3B N2B C2B N1B -0.1(3) . . . . ?
C3B N3B C1B Cl1B 178.79(12) . . . . ?
C3B N3B C1B N1B -0.9(3) . . . . ?
C3B N4B C4B C5B -94.2(2) . . . . ?
C4B N4B C3B N2B -4.9(3) . . . . ?
C4B N4B C3B N3B 175.45(16) . . . . ?
C4B C5B C6B C7B -177.11(16) . . . . ?
N4A C4A C5A C6A -62.8(2) . . . . ?
C1A N1A C2A Cl2A 178.95(12) . . . . ?
C1A N1A C2A N2A -0.3(3) . . . . ?
C1A N3A C3A N2A 0.6(2) . . . . ?
C1A N3A C3A N4A -179.29(15) . . . . ?
C2A N1A C1A Cl1A -179.10(12) . . . . ?
C2A N1A C1A N3A -0.4(3) . . . . ?
C2A N2A C3A N3A -1.1(2) . . . . ?
C2A N2A C3A N4A 178.75(15) . . . . ?
C3A N2A C2A Cl2A -178.23(12) . . . . ?
C3A N2A C2A N1A 1.0(3) . . . . ?
C3A N3A C1A Cl1A 178.91(12) . . . . ?
C3A N3A C1A N1A 0.3(3) . . . . ?
C3A N4A C4A C5A 102.4(2) . . . . ?
C4A N4A C3A N2A -176.06(15) . . . . ?
C4A N4A C3A N3A 3.8(3) . . . . ?
C4A C5A C6A C7A -177.08(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT029_bm10_a              
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.913 Note  
RESPONSE: Data acquisition at Australian Synchrotron has one circle goniometer
geometry that leaves gaps in covering the reciprocal space for low symmetry
space groups (such as this one).
;
# end Validation Reply Form
