 
data_PO19039_033
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C17 H16 Cl N O' 
_chemical_formula_weight          285.76

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'
 'N'  'N'   0.0066   0.0035
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0116   0.0065
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl'  'Cl'   0.1553   0.1685
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       orthorhombic
_space_group_IT_number            33
_space_group_name_H-M_alt         'P n a 21'
_space_group_name_Hall            'P 2c -2n'
 
_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+1/2'
 'x+1/2, -y+1/2, z'
 '-x+1/2, y+1/2, z+1/2'
 
_cell_length_a                    16.012(3)
_cell_length_b                    15.318(3)
_cell_length_c                    5.5950(11)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1372.3(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     23071
_cell_measurement_theta_min       0.418
_cell_measurement_theta_max       33.575
 
_exptl_crystal_description        'needle'
_exptl_crystal_colour             'colorless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.383          
_exptl_crystal_F_000              600
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.057
_exptl_crystal_size_mid           0.022
_exptl_crystal_size_min           0.020
_exptl_absorpt_coefficient_mu     0.289
_shelx_estimated_absorpt_T_min    0.984
_shelx_estimated_absorpt_T_max    0.994
_exptl_absorpt_correction_type    empirical
_exptl_absorpt_correction_T_min   0.866
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'HKL3000sm Scalepack'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.730
_diffrn_radiation_type            synchrotron
_diffrn_source                    'PLSII 2D bending magnet'
_diffrn_measurement_device_type   'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method        'omega scan'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             12846
_diffrn_reflns_av_unetI/netI      0.0404
_diffrn_reflns_av_R_equivalents   0.0629
_diffrn_reflns_limit_h_min        -21
_diffrn_reflns_limit_h_max        21
_diffrn_reflns_limit_k_min        -20
_diffrn_reflns_limit_k_max        20
_diffrn_reflns_limit_l_min        -7
_diffrn_reflns_limit_l_max        7
_diffrn_reflns_theta_min          1.890
_diffrn_reflns_theta_max          28.996
_diffrn_reflns_theta_full         25.976
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.999
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              3366
_reflns_number_gt                 3180
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.818
_reflns_Friedel_fraction_max      1.000
_reflns_Friedel_fraction_full     1.000
 
_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        'PAL BL2D-SMDC Program'
_computing_cell_refinement        'HKL3000sm'
_computing_data_reduction         'HKL3000sm'
_computing_structure_solution     SHELXS
_computing_structure_refinement   SHELXL
_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)+(0.0638P)²+0.4651P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Flack x determined using 1351 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    0.06(2)
_chemical_absolute_configuration  ?
_refine_ls_number_reflns          3366
_refine_ls_number_parameters      193
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0449
_refine_ls_R_factor_gt            0.0428
_refine_ls_wR_factor_ref          0.1142
_refine_ls_wR_factor_gt           0.1125
_refine_ls_goodness_of_fit_ref    1.094
_refine_ls_restrained_S_all       1.094
_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
O1 O 0.51706(11) 0.43176(14) 0.5562(4) 0.0210(4) Uani 1 1 d . . . . .
C2 C 0.57859(15) 0.47810(19) 0.5893(5) 0.0176(5) Uani 1 1 d . . . . .
N3 N 0.59967(13) 0.54926(17) 0.4642(4) 0.0176(5) Uani 1 1 d . . . . .
H3 H 0.567(2) 0.572(2) 0.368(8) 0.026 Uiso 1 1 d . U . . .
C4 C 0.66964(15) 0.59808(19) 0.5665(5) 0.0162(5) Uani 1 1 d . . . . .
H4 H 0.649(2) 0.653(2) 0.678(7) 0.024 Uiso 1 1 d . U . . .
C5 C 0.71579(14) 0.52779(18) 0.7175(5) 0.0166(5) Uani 1 1 d . . . . .
H5 H 0.741(2) 0.555(2) 0.876(7) 0.025 Uiso 1 1 d . U . . .
C6 C 0.64425(16) 0.4640(2) 0.7843(5) 0.0203(6) Uani 1 1 d . . . . .
H6A H 0.664303 0.402815 0.784318 0.024 Uiso 1 1 calc R U . . .
H6AB H 0.621215 0.477872 0.944013 0.024 Uiso 1 1 calc R U . . .
C7 C 0.72333(14) 0.6402(2) 0.3732(5) 0.0167(5) Uani 1 1 d . . . . .
H7 H 0.737(2) 0.596(2) 0.260(7) 0.025 Uiso 1 1 d . U . . .
Cl8 Cl 0.65890(3) 0.71997(4) 0.21365(14) 0.02188(19) Uani 1 1 d . . . . .
C9 C 0.80135(16) 0.68563(19) 0.4581(5) 0.0171(5) Uani 1 1 d . . . . .
C10 C 0.87140(16) 0.6838(2) 0.3128(6) 0.0228(6) Uani 1 1 d . . . . .
H10 H 0.869622 0.652313 0.166580 0.027 Uiso 1 1 calc R U . . .
C11 C 0.94406(18) 0.7271(2) 0.3770(7) 0.0289(7) Uani 1 1 d . . . . .
H11 H 0.991236 0.726076 0.274102 0.035 Uiso 1 1 calc R U . . .
C12 C 0.94756(18) 0.7719(2) 0.5920(7) 0.0276(7) Uani 1 1 d . . . . .
H12 H 0.997022 0.802036 0.636549 0.033 Uiso 1 1 calc R U . . .
C13 C 0.87900(19) 0.77251(19) 0.7411(6) 0.0250(6) Uani 1 1 d . . . . .
H13 H 0.881799 0.802155 0.890024 0.030 Uiso 1 1 calc R U . . .
C14 C 0.80540(16) 0.72987(19) 0.6748(5) 0.0217(6) Uani 1 1 d . . . . .
H14 H 0.758203 0.731110 0.777581 0.026 Uiso 1 1 calc R U . . .
C15 C 0.78788(15) 0.48249(19) 0.5920(5) 0.0161(5) Uani 1 1 d . . . . .
C16 C 0.77721(17) 0.4347(2) 0.3804(5) 0.0215(6) Uani 1 1 d . . . . .
H16 H 0.723185 0.429558 0.311647 0.026 Uiso 1 1 calc R U . . .
C17 C 0.84494(18) 0.3950(2) 0.2707(6) 0.0247(7) Uani 1 1 d . . . . .
H17 H 0.837023 0.363407 0.126371 0.030 Uiso 1 1 calc R U . . .
C18 C 0.92390(19) 0.4010(2) 0.3694(7) 0.0285(7) Uani 1 1 d . . . . .
H18 H 0.970077 0.373906 0.292995 0.034 Uiso 1 1 calc R U . . .
C19 C 0.93534(17) 0.4469(2) 0.5807(7) 0.0285(7) Uani 1 1 d . . . . .
H19 H 0.989267 0.450261 0.650884 0.034 Uiso 1 1 calc R U . . .
C20 C 0.86803(15) 0.48786(19) 0.6896(6) 0.0211(6) Uani 1 1 d . . . . .
H20 H 0.876597 0.520036 0.832637 0.025 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
O1 C2 1.228(3) . ?
C2 N3 1.339(4) . ?
C2 C6 1.530(4) . ?
N3 C4 1.463(3) . ?
N3 H3 0.83(4) . ?
C4 C7 1.524(4) . ?
C4 C5 1.555(4) . ?
C4 H4 1.10(4) . ?
C5 C15 1.519(3) . ?
C5 C6 1.552(4) . ?
C5 H5 1.06(4) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C9 1.507(4) . ?
C7 Cl8 1.832(3) . ?
C7 H7 0.95(4) . ?
C9 C10 1.386(4) . ?
C9 C14 1.390(4) . ?
C10 C11 1.387(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.397(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C20 1.397(3) . ?
C15 C16 1.402(4) . ?
C16 C17 1.387(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
 
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
O1 C2 N3 126.4(3) . . ?
O1 C2 C6 125.2(3) . . ?
N3 C2 C6 108.3(2) . . ?
C2 N3 C4 113.9(2) . . ?
C2 N3 H3 122(3) . . ?
C4 N3 H3 121(3) . . ?
N3 C4 C7 111.8(2) . . ?
N3 C4 C5 102.8(2) . . ?
C7 C4 C5 114.2(2) . . ?
N3 C4 H4 112.6(17) . . ?
C7 C4 H4 104.6(19) . . ?
C5 C4 H4 111(2) . . ?
C15 C5 C6 112.6(2) . . ?
C15 C5 C4 115.2(2) . . ?
C6 C5 C4 102.50(19) . . ?
C15 C5 H5 106(2) . . ?
C6 C5 H5 109(2) . . ?
C4 C5 H5 112(2) . . ?
C2 C6 C5 104.3(2) . . ?
C2 C6 H6A 110.9 . . ?
C5 C6 H6A 110.9 . . ?
C2 C6 H6AB 110.9 . . ?
C5 C6 H6AB 110.9 . . ?
H6A C6 H6AB 108.9 . . ?
C9 C7 C4 116.1(2) . . ?
C9 C7 Cl8 108.2(2) . . ?
C4 C7 Cl8 108.08(17) . . ?
C9 C7 H7 110(2) . . ?
C4 C7 H7 108(2) . . ?
Cl8 C7 H7 106(2) . . ?
C10 C9 C14 118.9(2) . . ?
C10 C9 C7 118.5(2) . . ?
C14 C9 C7 122.6(2) . . ?
C9 C10 C11 121.2(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.5(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 119.9(3) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C20 C15 C16 118.2(2) . . ?
C20 C15 C5 119.4(3) . . ?
C16 C15 C5 122.4(2) . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 119.7(3) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C20 120.0(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C15 121.0(3) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
 
loop_
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
 _geom_hbond_publ_flag
N3 H3 O1  0.83(4) 2.21(4) 2.965(3) 153(3) 2_664 yes
 
_refine_diff_density_max    0.575
_refine_diff_density_min   -0.290
_refine_diff_density_rms    0.063





















