 
data_shelx
 
_audit_creation_method            SHELXL-2013
_chemical_name_systematic         ' a-(3,5-dichloro-2-pyridylamino)-o-cresol'

_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H10 Cl2 N2 O' 
_chemical_formula_weight          269.12

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'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.1642(12)
_cell_length_b                    8.6294(14)
_cell_length_c                    10.9154(17)
_cell_angle_alpha                 102.651(10)
_cell_angle_beta                  102.348(8)
_cell_angle_gamma                 111.997(8)
_cell_volume                      576.93(17)
_cell_formula_units_Z             2
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     1024 
_cell_measurement_theta_min       3.26 
_cell_measurement_theta_max       29.08 
_exptl_crystal_description        'Prism' 
_exptl_crystal_colour             'Colorless' 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.549          
_exptl_crystal_F_000              276
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           0.23 
_exptl_crystal_size_mid           0.20 
_exptl_crystal_size_min           0.19
_exptl_absorpt_coefficient_mu     0.545
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.882 
_exptl_absorpt_correction_T_max   0.902 
_exptl_absorpt_process_details    ? 
 

_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed tube'                        
_diffrn_measurement_device_type   'Rigaku Saturn 720+ CCD'  
_diffrn_measurement_method        'profile data from ω-scans' 
_diffrn_detector_area_resol_mean  28.5714 
_diffrn_reflns_number             4140
_diffrn_reflns_av_unetI/netI      0.0539
_diffrn_reflns_av_R_equivalents   0.0266
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        0
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          2.697
_diffrn_reflns_theta_max          30.046
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.851
_diffrn_measured_fraction_theta_full  0.925
_diffrn_reflns_Laue_measured_fraction_max    0.851
_diffrn_reflns_Laue_measured_fraction_full   0.925
_diffrn_reflns_point_group_measured_fraction_max   0.851
_diffrn_reflns_point_group_measured_fraction_full  0.925
_reflns_number_total              2882
_reflns_number_gt                 2215
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0770P)²] 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          2882
_refine_ls_number_parameters      155
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0584
_refine_ls_R_factor_gt            0.0446
_refine_ls_wR_factor_ref          0.1291
_refine_ls_wR_factor_gt           0.1213
_refine_ls_goodness_of_fit_ref    1.015
_refine_ls_restrained_S_all       1.015
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_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
Cl2 Cl 0.35519(8) 0.79248(6) 0.95923(5) 0.03062(16) Uani 1 1 d . . . . .
Cl1 Cl 0.19618(8) 0.29212(7) 1.20022(5) 0.03196(16) Uani 1 1 d . . . . .
O O 0.0428(2) 0.06600(18) 0.37414(14) 0.0236(3) Uani 1 1 d . . . . .
H1 H -0.0123 -0.0357 0.3225 0.035 Uiso 1 1 calc R U . . .
N1 N 0.2261(3) 0.4827(2) 0.72126(16) 0.0250(4) Uani 1 1 d . . . . .
H1A H 0.2626 0.5909 0.7247 0.030 Uiso 1 1 calc R U . . .
C11 C 0.2702(3) 0.5332(2) 1.06957(19) 0.0243(4) Uani 1 1 d . . . . .
H11 H 0.3118 0.6205 1.1505 0.029 Uiso 1 1 calc R U . . .
N2 N 0.1408(3) 0.2713(2) 0.82576(17) 0.0243(4) Uani 1 1 d . . . . .
C12 C 0.2739(3) 0.5750(2) 0.95573(19) 0.0221(4) Uani 1 1 d . . . . .
C6 C -0.1128(3) 0.1122(2) 0.39707(19) 0.0207(4) Uani 1 1 d . . . . .
C7 C 0.1820(3) 0.3525(2) 0.59576(19) 0.0228(4) Uani 1 1 d . . . . .
H7A H 0.2286 0.2655 0.6140 0.027 Uiso 1 1 calc R U . . .
H7B H 0.2654 0.4115 0.5461 0.027 Uiso 1 1 calc R U . . .
C10 C 0.2022(3) 0.3560(3) 1.06024(19) 0.0237(4) Uani 1 1 d . . . . .
C8 C 0.2126(3) 0.4419(2) 0.83256(19) 0.0216(4) Uani 1 1 d . . . . .
C9 C 0.1377(3) 0.2309(3) 0.9381(2) 0.0253(4) Uani 1 1 d . . . . .
H9 H 0.0896 0.1127 0.9327 0.030 Uiso 1 1 calc R U . . .
C1 C -0.0501(3) 0.2573(2) 0.51007(18) 0.0206(4) Uani 1 1 d . . . . .
C2 C -0.2041(3) 0.3076(3) 0.5377(2) 0.0273(4) Uani 1 1 d . . . . .
H2 H -0.1650 0.4038 0.6125 0.033 Uiso 1 1 calc R U . . .
C5 C -0.3223(3) 0.0231(3) 0.3135(2) 0.0275(4) Uani 1 1 d . . . . .
H5 H -0.3619 -0.0720 0.2378 0.033 Uiso 1 1 calc R U . . .
C3 C -0.4156(3) 0.2162(3) 0.4551(2) 0.0320(5) Uani 1 1 d . . . . .
H3 H -0.5173 0.2499 0.4756 0.038 Uiso 1 1 calc R U . . .
C4 C -0.4734(3) 0.0756(3) 0.3429(2) 0.0319(5) Uani 1 1 d . . . . .
H4 H -0.6140 0.0158 0.2866 0.038 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
Cl2 C12 1.7327(19) . ?
Cl1 C10 1.7380(19) . ?
O C6 1.368(2) . ?
O H1 0.8200 . ?
N1 C8 1.349(3) . ?
N1 C7 1.454(2) . ?
N1 H1A 0.8600 . ?
C11 C12 1.370(3) . ?
C11 C10 1.392(3) . ?
C11 H11 0.9300 . ?
N2 C8 1.344(2) . ?
N2 C9 1.349(3) . ?
C12 C8 1.419(3) . ?
C6 C5 1.385(3) . ?
C6 C1 1.399(3) . ?
C7 C1 1.513(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C10 C9 1.374(3) . ?
C9 H9 0.9300 . ?
C1 C2 1.392(3) . ?
C2 C3 1.393(3) . ?
C2 H2 0.9300 . ?
C5 C4 1.391(3) . ?
C5 H5 0.9300 . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
 
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
C6 O H1 109.5 . . ?
C8 N1 C7 123.21(17) . . ?
C8 N1 H1A 118.4 . . ?
C7 N1 H1A 118.4 . . ?
C12 C11 C10 117.93(17) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
C8 N2 C9 118.98(17) . . ?
C11 C12 C8 120.96(17) . . ?
C11 C12 Cl2 120.62(15) . . ?
C8 C12 Cl2 118.42(15) . . ?
O C6 C5 122.79(17) . . ?
O C6 C1 116.61(16) . . ?
C5 C6 C1 120.60(18) . . ?
N1 C7 C1 114.31(16) . . ?
N1 C7 H7A 108.7 . . ?
C1 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C1 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C10 C11 119.11(18) . . ?
C9 C10 Cl1 120.03(15) . . ?
C11 C10 Cl1 120.86(15) . . ?
N2 C8 N1 118.81(17) . . ?
N2 C8 C12 119.75(17) . . ?
N1 C8 C12 121.44(17) . . ?
N2 C9 C10 123.19(18) . . ?
N2 C9 H9 118.4 . . ?
C10 C9 H9 118.4 . . ?
C2 C1 C6 118.41(17) . . ?
C2 C1 C7 123.28(17) . . ?
C6 C1 C7 118.30(17) . . ?
C1 C2 C3 121.08(19) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C6 C5 C4 120.02(19) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
 
_refine_diff_density_max    0.462
_refine_diff_density_min   -0.418
_refine_diff_density_rms    0.081

_shelxl_version_number 2013-4

# start validation Reply form
_vrf_PLAT029

;
PROBLEM:
_diffrn_measured_fraction_theta_full value Low

RESPONSE:
This is a P-1 triclinic structure for which completeness is hard to obtain at this sin(theta)/lambda. 
Overall completness of 85.2% is lower than would be like, but is nevertheless acceptable.
;


# end validation Reply form



# start Validation Reply Form
_vrf_PLAT029_I
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.925 Why?
RESPONSE: 
Data collection strategy was slightly compromised in completeness, but it is 
only slightly below the gold standard threshold. Besides, the theta(max) of 
30 somewhat compensates for this issue. All statistical figures-of-merit are 
fine and the model is good. No associated issues arise as a consequence of 
this slight shortfall; these would arise if this threshold caused a 
practical problem..
;
# end Validation Reply Form
