 
data_shelx
 
_audit_creation_method            SHELXL-2013
_chemical_name_systematic          'a-(4-methyl-2-pyridylamino)-o-cresol'

 

_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H14 N2 O' 
_chemical_formula_weight          214.26

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       orthorhombic
_space_group_IT_number            19
_space_group_name_H-M_alt         'P 21 21 21'
_space_group_name_Hall            'P 2ac 2ab'
 
_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+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    6.3693(13)
_cell_length_b                    11.382(2)
_cell_length_c                    15.292(3)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1108.6(4)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     1024
_cell_measurement_theta_min       3.26
_cell_measurement_theta_max       29.08
_cell_measurement_temperature     150(2) 
_exptl_crystal_description        'Prism' 
_exptl_crystal_colour             'Colorless' 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.284          
_exptl_crystal_F_000              456
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           0.46 
_exptl_crystal_size_mid           0.19 
_exptl_crystal_size_min           0.09 
_exptl_absorpt_coefficient_mu     0.083
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.963 
_exptl_absorpt_correction_T_max   0.993 
_exptl_absorpt_process_details    ? 
 
_exptl_special_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             10218
_diffrn_reflns_av_unetI/netI      0.0372
_diffrn_reflns_av_R_equivalents   0.0278
_diffrn_reflns_limit_h_min        0
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        0
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          2.664
_diffrn_reflns_theta_max          30.062
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.937
_diffrn_measured_fraction_theta_full  0.961
_diffrn_reflns_Laue_measured_fraction_max    0.937
_diffrn_reflns_Laue_measured_fraction_full   0.961
_diffrn_reflns_point_group_measured_fraction_max   0.925
_diffrn_reflns_point_group_measured_fraction_full  0.961
_reflns_number_total              2997
_reflns_number_gt                 2884
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.707
_reflns_Friedel_fraction_max      0.908
_reflns_Friedel_fraction_full     0.960
 
_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)+(0.0532P)²+0.0630P] 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_abs_structure_details
;
 Flack x determined using 1129 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack    0.6(6)
_chemical_absolute_configuration  ?
_refine_ls_number_reflns          2997
_refine_ls_number_parameters      147
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0394
_refine_ls_R_factor_gt            0.0376
_refine_ls_wR_factor_ref          0.1008
_refine_ls_wR_factor_gt           0.0994
_refine_ls_goodness_of_fit_ref    1.076
_refine_ls_restrained_S_all       1.076
_refine_ls_shift/su_max           0.043
_refine_ls_shift/su_mean          0.002
 
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
O O 0.0824(2) 0.95660(10) 0.58469(10) 0.0375(3) Uani 1 1 d . . . . .
H1 H -0.0112 1.0041 0.5745 0.056 Uiso 1 1 calc R U . . .
N1 N -0.4674(2) 0.98487(12) 0.58452(10) 0.0296(3) Uani 1 1 d . . . . .
H1A H -0.5863 0.9660 0.6072 0.036 Uiso 1 1 calc R U . . .
N2 N -0.2000(2) 1.12231(11) 0.57154(8) 0.0254(3) Uani 1 1 d . . . . .
C1 C -0.2077(3) 0.81990(13) 0.59426(10) 0.0254(3) Uani 1 1 d . . . . .
C9 C -0.1382(3) 1.23572(14) 0.57755(10) 0.0285(3) Uani 1 1 d . . . . .
H9 H -0.0011 1.2540 0.5615 0.034 Uiso 1 1 calc R U . . .
C6 C -0.0034(3) 0.85493(13) 0.61557(11) 0.0281(3) Uani 1 1 d . . . . .
C8 C -0.3985(3) 1.09716(13) 0.59433(9) 0.0245(3) Uani 1 1 d . . . . .
C2 C -0.2790(3) 0.71191(14) 0.62657(11) 0.0314(4) Uani 1 1 d . . . . .
H2 H -0.4139 0.6868 0.6127 0.038 Uiso 1 1 calc R U . . .
C12 C -0.5350(3) 1.18384(14) 0.62862(10) 0.0273(3) Uani 1 1 d . . . . .
H12 H -0.6690 1.1631 0.6473 0.033 Uiso 1 1 calc R U . . .
C7 C -0.3493(3) 0.89441(14) 0.53723(11) 0.0286(3) Uani 1 1 d . . . . .
H7A H -0.2643 0.9323 0.4928 0.034 Uiso 1 1 calc R U . . .
H7B H -0.4481 0.8432 0.5076 0.034 Uiso 1 1 calc R U . . .
C10 C -0.2643(3) 1.32508(15) 0.60567(10) 0.0313(3) Uani 1 1 d . . . . .
H10 H -0.2157 1.4021 0.6060 0.038 Uiso 1 1 calc R U . . .
C4 C 0.0494(3) 0.67756(17) 0.69904(11) 0.0361(4) Uani 1 1 d . . . . .
H4 H 0.1349 0.6305 0.7337 0.043 Uiso 1 1 calc R U . . .
C11 C -0.4695(3) 1.29857(14) 0.63425(10) 0.0299(4) Uani 1 1 d . . . . .
C3 C -0.1528(3) 0.64153(14) 0.67885(11) 0.0349(4) Uani 1 1 d . . . . .
H3 H -0.2036 0.5705 0.7002 0.042 Uiso 1 1 calc R U . . .
C5 C 0.1234(3) 0.78335(15) 0.66759(12) 0.0338(4) Uani 1 1 d . . . . .
H5 H 0.2592 0.8072 0.6812 0.041 Uiso 1 1 calc R U . . .
C13 C -0.6123(3) 1.39280(16) 0.66912(12) 0.0377(4) Uani 1 1 d . . . . .
H13A H -0.7481 1.3599 0.6810 0.057 Uiso 1 1 calc R U . . .
H13B H -0.6256 1.4543 0.6265 0.057 Uiso 1 1 calc R U . . .
H13C H -0.5543 1.4244 0.7221 0.057 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
O C6 1.364(2) . ?
O H1 0.8200 . ?
N1 C8 1.360(2) . ?
N1 C7 1.466(2) . ?
N1 H1A 0.8600 . ?
N2 C8 1.342(2) . ?
N2 C9 1.353(2) . ?
C1 C6 1.399(2) . ?
C1 C2 1.400(2) . ?
C1 C7 1.514(2) . ?
C9 C10 1.366(2) . ?
C9 H9 0.9300 . ?
C6 C5 1.396(2) . ?
C8 C12 1.416(2) . ?
C2 C3 1.388(3) . ?
C2 H2 0.9300 . ?
C12 C11 1.374(2) . ?
C12 H12 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C10 C11 1.411(3) . ?
C10 H10 0.9300 . ?
C4 C5 1.380(3) . ?
C4 C3 1.386(3) . ?
C4 H4 0.9300 . ?
C11 C13 1.504(2) . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C6 O H1 109.5 . . ?
C8 N1 C7 123.31(14) . . ?
C8 N1 H1A 118.3 . . ?
C7 N1 H1A 118.3 . . ?
C8 N2 C9 117.40(14) . . ?
C6 C1 C2 118.00(16) . . ?
C6 C1 C7 121.89(14) . . ?
C2 C1 C7 120.10(15) . . ?
N2 C9 C10 124.11(16) . . ?
N2 C9 H9 117.9 . . ?
C10 C9 H9 117.9 . . ?
O C6 C5 117.39(16) . . ?
O C6 C1 122.27(15) . . ?
C5 C6 C1 120.30(15) . . ?
N2 C8 N1 118.41(14) . . ?
N2 C8 C12 121.74(14) . . ?
N1 C8 C12 119.85(15) . . ?
C3 C2 C1 121.45(17) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C11 C12 C8 119.93(16) . . ?
C11 C12 H12 120.0 . . ?
C8 C12 H12 120.0 . . ?
N1 C7 C1 114.52(13) . . ?
N1 C7 H7A 108.6 . . ?
C1 C7 H7A 108.6 . . ?
N1 C7 H7B 108.6 . . ?
C1 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C9 C10 C11 118.90(16) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C5 C4 C3 119.88(17) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C12 C11 C10 117.75(16) . . ?
C12 C11 C13 121.09(17) . . ?
C10 C11 C13 121.17(16) . . ?
C4 C3 C2 119.71(16) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C4 C5 C6 120.66(18) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
 
_refine_diff_density_max    0.182
_refine_diff_density_min   -0.249
_refine_diff_density_rms    0.036

_shelxl_version_number 2013-4

# start validation Reply form
_vrf_STRVA01

;
PROBLEM:
_refine_ls_abs_structure_Flack 0.600

RESPONSE:
The Flack paramter cannot be used reliably in this study since the heaviest element is oxygen
;

_vrf_PLAT907

;
PROBLEM:
Flack x > 0.5, Structure Needs to be Inverted? . 0.60 Check

RESPONSE:
The Flack paramter cannot be used reliably in this study since the heaviest element is oxygen
;


# end validation Reply form





