 
data_H2PNZ_298K
 
_audit_creation_method            'SHELXL-2017/1'
_shelx_SHELXL_version_number      '2017/1'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H10 Cl1.19 N2 O0.40' 
_chemical_formula_weight          230.69

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0034   0.0017
 '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'   0.1507   0.1611
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0066   0.0034
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0114   0.0062
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            12
_space_group_name_H-M_alt         'C 2/m'
_space_group_name_Hall            '-C 2y'
 
_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'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z'
 '-x, -y, -z'
 'x, -y, z'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z'
 
_cell_length_a                    7.0475(5)
_cell_length_b                    27.970(2)
_cell_length_c                    11.3860(8)
_cell_angle_alpha                 90
_cell_angle_beta                  102.511(4)
_cell_angle_gamma                 90
_cell_volume                      2191.1(3)
_cell_formula_units_Z             8
_cell_measurement_temperature     298(2)
_cell_measurement_reflns_used      19474
_cell_measurement_theta_max        35.57
_cell_measurement_theta_min        1.456 
 
_exptl_crystal_description       Needle
_exptl_crystal_colour             Black
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.399          
_exptl_crystal_F_000              955
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.070
_exptl_crystal_size_mid           0.050
_exptl_crystal_size_min           0.040
_exptl_absorpt_coefficient_mu     0.361
_shelx_estimated_absorpt_T_min    0.975
_shelx_estimated_absorpt_T_max    0.986
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       298(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube' _diffrn_measurement_device_type    CCD 
_diffrn_measurement_method        'Omega and phi scan'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             19474
_diffrn_reflns_av_unetI/netI      0.1189
_diffrn_reflns_av_R_equivalents   0.0529
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -45
_diffrn_reflns_limit_k_max        45
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          1.456
_diffrn_reflns_theta_max          35.574
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.982
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    0.982
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.982
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              5036
_reflns_number_gt                 2230
_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         'APEX2 software Suite'
_computing_cell_refinement         'APEX2 software Suite'
_computing_data_reduction          'APEX2 software Suite'
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1034P)²+0.8670P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          5036
_refine_ls_number_parameters      152
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1509
_refine_ls_R_factor_gt            0.0795
_refine_ls_wR_factor_ref          0.2963
_refine_ls_wR_factor_gt           0.2307
_refine_ls_goodness_of_fit_ref    1.049
_refine_ls_restrained_S_all       1.049
_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
Cl01 Cl 0.18935(13) 0.500000 0.86382(6) 0.0507(3) Uani 1 2 d S T P . .
O1W O 0.3789(5) 0.500000 0.1478(3) 0.0649(9) Uani 0.8 2 d S T P . .
Cl02 Cl 0.42438(18) 0.75230(3) 0.36113(9) 0.0695(5) Uani 0.687(3) 1 d . . P . .
N003 N 0.2395(3) 0.500000 0.60140(18) 0.0327(5) Uani 1 2 d S T P . .
H003 H 0.229583 0.499999 0.675356 0.039 Uiso 1 2 calc R U P . .
N004 N 0.2775(3) 0.500000 0.36816(18) 0.0321(5) Uani 1 2 d S T P . .
H004 H 0.290703 0.500000 0.294827 0.039 Uiso 1 2 calc R U P . .
N5 N 0.4809(3) 0.75157(6) 0.1166(2) 0.0467(5) Uani 1 1 d . . . . .
H5 H 0.469332 0.751530 0.190289 0.056 Uiso 1 1 calc R U . . .
C006 C 0.2673(2) 0.45713(6) 0.42465(15) 0.0297(4) Uani 1 1 d . . . . .
C007 C 0.2471(3) 0.45713(6) 0.54544(15) 0.0298(4) Uani 1 1 d . . . . .
C008 C 0.2331(3) 0.41380(7) 0.60450(18) 0.0384(4) Uani 1 1 d . . . . .
H008 H 0.218001 0.413622 0.683636 0.046 Uiso 1 1 calc R U . . .
C009 C 0.2756(3) 0.41353(7) 0.36558(18) 0.0399(4) Uani 1 1 d . . . . .
H009 H 0.288968 0.413092 0.286091 0.048 Uiso 1 1 calc R U . . .
C00B C 0.4903(3) 0.70882(7) 0.0603(2) 0.0426(5) Uani 1 1 d . . . . .
C00C C 0.4893(3) 0.79457(7) 0.0601(2) 0.0464(5) Uani 1 1 d . . . . .
C00D C 0.2640(3) 0.37146(8) 0.4256(2) 0.0468(5) Uani 1 1 d . . . . .
H00D H 0.270878 0.342503 0.386576 0.056 Uiso 1 1 calc R U . . .
C00E C 0.2420(3) 0.37162(8) 0.5446(2) 0.0462(5) Uani 1 1 d . . . . .
H00E H 0.233174 0.342764 0.583637 0.055 Uiso 1 1 calc R U . . .
C00F C 0.4811(3) 0.66525(8) 0.1199(2) 0.0491(6) Uani 1 1 d . . . . .
H00F H 0.468928 0.664829 0.199569 0.059 Uiso 1 1 calc R U . . .
C00G C 0.4766(3) 0.83804(8) 0.1191(3) 0.0536(6) Uani 1 1 d . . . . .
H00G H 0.461077 0.838304 0.198181 0.064 Uiso 1 1 calc R U . . .
C00H C 0.4871(4) 0.88022(8) 0.0593(3) 0.0610(8) Uani 1 1 d . . . . .
H00H H 0.477008 0.909116 0.097899 0.073 Uiso 1 1 calc R U . . .
C00I C 0.4903(4) 0.62318(8) 0.0589(3) 0.0565(7) Uani 1 1 d . . . . .
H00I H 0.483432 0.594222 0.097927 0.068 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
N003 C007 1.3644(19) . ?
N003 C007 1.3644(19) 6_565 ?
N004 C006 1.3699(19) 6_565 ?
N004 C006 1.3699(19) . ?
N5 C00B 1.365(3) . ?
N5 C00C 1.371(3) . ?
C006 C009 1.400(2) . ?
C006 C007 1.413(2) . ?
C007 C008 1.400(2) . ?
C008 C00E 1.371(3) . ?
C009 C00D 1.372(3) . ?
C00B C00F 1.403(3) . ?
C00B C00B 1.409(4) 2_655 ?
C00C C00G 1.401(3) . ?
C00C C00C 1.410(5) 2_655 ?
C00D C00E 1.397(3) . ?
C00F C00I 1.375(3) . ?
C00G C00H 1.372(4) . ?
C00H C00H 1.401(6) 2_655 ?
C00I C00I 1.378(5) 2_655 ?
 
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
C007 N003 C007 123.03(19) . 6_565 ?
C006 N004 C006 122.2(2) 6_565 . ?
C00B N5 C00C 122.4(2) . . ?
N004 C006 C009 121.66(16) . . ?
N004 C006 C007 118.92(15) . . ?
C009 C006 C007 119.42(16) . . ?
N003 C007 C008 121.52(16) . . ?
N003 C007 C006 118.48(15) . . ?
C008 C007 C006 120.00(16) . . ?
C00E C008 C007 119.37(18) . . ?
C00D C009 C006 119.64(18) . . ?
N5 C00B C00F 121.4(2) . . ?
N5 C00B C00B 118.86(13) . 2_655 ?
C00F C00B C00B 119.70(14) . 2_655 ?
N5 C00C C00G 121.5(2) . . ?
N5 C00C C00C 118.70(13) . 2_655 ?
C00G C00C C00C 119.80(15) . 2_655 ?
C009 C00D C00E 120.76(18) . . ?
C008 C00E C00D 120.80(18) . . ?
C00I C00F C00B 119.2(2) . . ?
C00H C00G C00C 119.5(3) . . ?
C00G C00H C00H 120.70(16) . 2_655 ?
C00F C00I C00I 121.14(15) . 2_655 ?
 
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
C006 N004 C006 C009 179.25(15) 6_565 . . . ?
C006 N004 C006 C007 -0.5(4) 6_565 . . . ?
C007 N003 C007 C008 -178.06(15) 6_565 . . . ?
C007 N003 C007 C006 1.2(4) 6_565 . . . ?
N004 C006 C007 N003 -0.4(3) . . . . ?
C009 C006 C007 N003 179.91(18) . . . . ?
N004 C006 C007 C008 178.95(18) . . . . ?
C009 C006 C007 C008 -0.8(3) . . . . ?
N003 C007 C008 C00E -179.8(2) . . . . ?
C006 C007 C008 C00E 0.9(3) . . . . ?
N004 C006 C009 C00D -179.7(2) . . . . ?
C007 C006 C009 C00D 0.0(3) . . . . ?
C00C N5 C00B C00F -179.89(19) . . . . ?
C00C N5 C00B C00B 0.1(4) . . . 2_655 ?
C00B N5 C00C C00G 179.06(19) . . . . ?
C00B N5 C00C C00C -0.8(4) . . . 2_655 ?
C006 C009 C00D C00E 0.7(3) . . . . ?
C007 C008 C00E C00D -0.2(3) . . . . ?
C009 C00D C00E C008 -0.6(4) . . . . ?
N5 C00B C00F C00I 179.7(2) . . . . ?
C00B C00B C00F C00I -0.3(4) 2_655 . . . ?
N5 C00C C00G C00H 179.5(2) . . . . ?
C00C C00C C00G C00H -0.7(4) 2_655 . . . ?
C00C C00G C00H C00H -0.8(4) . . . 2_655 ?
C00B C00F C00I C00I 0.4(4) . . . 2_655 ?
 
_refine_diff_density_max    0.664
_refine_diff_density_min   -1.043
_refine_diff_density_rms    0.078



