 
data_P-1
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C5 H16 N2, 2(Cl)'
_chemical_formula_sum
 'C5 H16 Cl2 N2' 
_chemical_formula_weight          175.10

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 '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'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    5.68920(10)
_cell_length_b                    7.09760(10)
_cell_length_c                    11.5466(3)
_cell_angle_alpha                 76.351(2)
_cell_angle_beta                  82.677(2)
_cell_angle_gamma                 84.635(2)
_cell_volume                      448.411(16)
_cell_formula_units_Z             2
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     6135
_cell_measurement_theta_min       2.9480
_cell_measurement_theta_max       31.8520
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.297          
_exptl_crystal_F_000              188
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.190
_exptl_crystal_size_mid           0.190
_exptl_crystal_size_min           0.180
_exptl_absorpt_coefficient_mu     0.652
_shelx_estimated_absorpt_T_min    0.886
_shelx_estimated_absorpt_T_max    0.892
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.883
_exptl_absorpt_correction_T_max   0.889
_exptl_absorpt_process_details    'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Rotating-anode X-ray tube'
_diffrn_measurement_device_type   'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method        'four-circle diffractometer'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             6652
_diffrn_reflns_av_unetI/netI      0.0255
_diffrn_reflns_av_R_equivalents   0.0353
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          2.960
_diffrn_reflns_theta_max          27.243
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   1.000
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    1.000
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   1.000
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              2006
_reflns_number_gt                 1858
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction         'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution     'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement   'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material   'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0551P)²+0.0957P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef        0.65(2)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          2006
_refine_ls_number_parameters      87
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0320
_refine_ls_R_factor_gt            0.0302
_refine_ls_wR_factor_ref          0.0869
_refine_ls_wR_factor_gt           0.0857
_refine_ls_goodness_of_fit_ref    1.007
_refine_ls_restrained_S_all       1.007
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
Cl1 Cl 0.26160(6) 0.29000(5) 0.50520(3) 0.03380(15) Uani 1 1 d . . . . .
Cl2 Cl 0.40589(7) 0.28504(5) 0.87770(3) 0.04300(16) Uani 1 1 d . . . . .
N2 N -0.03304(17) 0.19537(15) 0.20241(9) 0.0241(2) Uani 1 1 d . . . . .
N1 N 0.2902(2) -0.26830(15) 0.35914(10) 0.0291(3) Uani 1 1 d . . . . .
H1A H 0.3531 -0.3058 0.2929 0.044 Uiso 1 1 calc R U . . .
H1B H 0.1603 -0.3315 0.3896 0.044 Uiso 1 1 calc R U . . .
H1C H 0.3951 -0.2949 0.4127 0.044 Uiso 1 1 calc R U . . .
C2 C 0.0793(2) -0.00873(18) 0.22530(12) 0.0279(3) Uani 1 1 d . . . . .
H2B H 0.1793 -0.0266 0.1536 0.034 Uiso 1 1 calc R U . . .
H2A H -0.0450 -0.0990 0.2406 0.034 Uiso 1 1 calc R U . . .
C3 C -0.1987(2) 0.2299(2) 0.30873(12) 0.0338(3) Uani 1 1 d . . . . .
H3A H -0.2969 0.1221 0.3382 0.051 Uiso 1 1 calc R U . . .
H3B H -0.2971 0.3469 0.2852 0.051 Uiso 1 1 calc R U . . .
H3C H -0.1080 0.2429 0.3707 0.051 Uiso 1 1 calc R U . . .
C1 C 0.2272(2) -0.05777(18) 0.32982(12) 0.0315(3) Uani 1 1 d . . . . .
H1E H 0.3705 0.0126 0.3091 0.038 Uiso 1 1 calc R U . . .
H1D H 0.1380 -0.0194 0.3989 0.038 Uiso 1 1 calc R U . . .
C4 C -0.1705(3) 0.2207(2) 0.09600(12) 0.0356(3) Uani 1 1 d . . . . .
H4A H -0.0624 0.2124 0.0261 0.053 Uiso 1 1 calc R U . . .
H4B H -0.2567 0.3455 0.0831 0.053 Uiso 1 1 calc R U . . .
H4C H -0.2799 0.1204 0.1110 0.053 Uiso 1 1 calc R U . . .
C5 C 0.1493(2) 0.3436(2) 0.17408(13) 0.0339(3) Uani 1 1 d . . . . .
H5A H 0.2360 0.3301 0.2420 0.051 Uiso 1 1 calc R U . . .
H5B H 0.0718 0.4715 0.1559 0.051 Uiso 1 1 calc R U . . .
H5C H 0.2569 0.3240 0.1062 0.051 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
N2 C5 1.4982(16) . ?
N2 C3 1.5032(16) . ?
N2 C2 1.5053(15) . ?
N2 C4 1.5058(15) . ?
N1 C1 1.4723(16) . ?
C2 C1 1.5139(17) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C5 N2 C3 108.19(10) . . ?
C5 N2 C2 111.85(10) . . ?
C3 N2 C2 111.44(10) . . ?
C5 N2 C4 108.82(10) . . ?
C3 N2 C4 109.48(10) . . ?
C2 N2 C4 107.02(9) . . ?
N2 C2 C1 113.77(10) . . ?
N1 C1 C2 109.36(10) . . ?
 
_refine_diff_density_max    0.283
_refine_diff_density_min   -0.304
_refine_diff_density_rms    0.056



