 
data_PO19040_015
 
_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
 'C18 H18 Cl N O' 
_chemical_formula_weight          299.78

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0027   0.0015
 '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'   0.0054   0.0030
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0098   0.0055
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl'  'Cl'   0.1392   0.1463
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            15
_space_group_name_H-M_alt         'C 2/c'
_space_group_name_Hall            '-C 2yc'
 
_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'
 '-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                    24.474(5)
_cell_length_b                    5.4150(11)
_cell_length_c                    23.818(5)
_cell_angle_alpha                 90
_cell_angle_beta                  93.99(3)
_cell_angle_gamma                 90
_cell_volume                      3148.9(11)
_cell_formula_units_Z             8
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     33091
_cell_measurement_theta_min       0.390
_cell_measurement_theta_max       33.875
 
_exptl_crystal_description        'rod'
_exptl_crystal_colour             'colorless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.265          
_exptl_crystal_F_000              1264
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.078
_exptl_crystal_size_mid           0.032
_exptl_crystal_size_min           0.024
_exptl_absorpt_coefficient_mu     0.211
_shelx_estimated_absorpt_T_min    0.984
_shelx_estimated_absorpt_T_max    0.995
_exptl_absorpt_correction_type    empirical
_exptl_absorpt_correction_T_min   0.883
_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      0.680
_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             17419
_diffrn_reflns_av_unetI/netI      0.0526
_diffrn_reflns_av_R_equivalents   0.0772
_diffrn_reflns_limit_h_min        -35
_diffrn_reflns_limit_h_max        35
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        7
_diffrn_reflns_limit_l_min        -35
_diffrn_reflns_limit_l_max        35
_diffrn_reflns_theta_min          1.596
_diffrn_reflns_theta_max          29.999
_diffrn_reflns_theta_full         24.079
_diffrn_measured_fraction_theta_max   0.986
_diffrn_measured_fraction_theta_full  0.993
_diffrn_reflns_Laue_measured_fraction_max    0.986
_diffrn_reflns_Laue_measured_fraction_full   0.993
_diffrn_reflns_point_group_measured_fraction_max   0.986
_diffrn_reflns_point_group_measured_fraction_full  0.993
_reflns_number_total              5156
_reflns_number_gt                 4312
_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        '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)+(0.0838P)²+0.3946P] 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_number_reflns          5156
_refine_ls_number_parameters      202
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0555
_refine_ls_R_factor_gt            0.0472
_refine_ls_wR_factor_ref          0.1470
_refine_ls_wR_factor_gt           0.1421
_refine_ls_goodness_of_fit_ref    1.154
_refine_ls_restrained_S_all       1.154
_refine_ls_shift/su_max           0.003
_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 0.51311(3) 0.74614(16) 0.44995(4) 0.01418(18) Uani 1 1 d . . . . .
C2 C 0.46452(5) 0.7090(2) 0.45850(5) 0.0106(2) Uani 1 1 d . . . . .
N3 N 0.43484(4) 0.84406(18) 0.49266(4) 0.01127(19) Uani 1 1 d . . . . .
H3 H 0.4477(7) 0.960(3) 0.5110(7) 0.017 Uiso 1 1 d . U . . .
C4 C 0.37941(4) 0.7524(2) 0.49788(5) 0.0104(2) Uani 1 1 d . . . . .
H4 H 0.3533(6) 0.886(3) 0.4955(6) 0.016 Uiso 1 1 d . U . . .
C5 C 0.37041(5) 0.5735(2) 0.44747(5) 0.0110(2) Uani 1 1 d . . . . .
H5 H 0.3508(6) 0.428(3) 0.4619(7) 0.017 Uiso 1 1 d . U . . .
C6 C 0.42884(5) 0.5046(2) 0.43298(5) 0.0128(2) Uani 1 1 d . . . . .
H6A H 0.439802 0.342722 0.449497 0.015 Uiso 1 1 calc R U . . .
H6B H 0.431368 0.496927 0.391711 0.015 Uiso 1 1 calc R U . . .
C7 C 0.37556(4) 0.6252(2) 0.55533(5) 0.0110(2) Uani 1 1 d . . . . .
H7 H 0.3950(6) 0.472(3) 0.5581(7) 0.017 Uiso 1 1 d . U . . .
Cl8 Cl 0.30406(2) 0.54390(6) 0.56008(2) 0.01912(11) Uani 1 1 d . . . . .
C9 C 0.39588(5) 0.7849(2) 0.60428(5) 0.0124(2) Uani 1 1 d . . . . .
C10 C 0.36680(5) 0.9923(2) 0.62007(5) 0.0170(2) Uani 1 1 d . . . . .
H10 H 0.332074 1.028846 0.601632 0.020 Uiso 1 1 calc R U . . .
C11 C 0.38862(6) 1.1454(2) 0.66276(6) 0.0232(3) Uani 1 1 d . . . . .
H11 H 0.368691 1.286102 0.673573 0.028 Uiso 1 1 calc R U . . .
C12 C 0.43930(7) 1.0934(3) 0.68959(5) 0.0251(3) Uani 1 1 d . . . . .
H12 H 0.454116 1.199225 0.718608 0.030 Uiso 1 1 calc R U . . .
C13 C 0.46860(6) 0.8873(3) 0.67428(5) 0.0226(3) Uani 1 1 d . . . . .
H13 H 0.503439 0.852156 0.692645 0.027 Uiso 1 1 calc R U . . .
C14 C 0.44653(5) 0.7320(2) 0.63171(5) 0.0159(2) Uani 1 1 d . . . . .
H14 H 0.466203 0.589606 0.621459 0.019 Uiso 1 1 calc R U . . .
C15 C 0.33775(5) 0.6953(2) 0.39740(5) 0.0130(2) Uani 1 1 d . . . . .
H15A H 0.302970 0.761722 0.410037 0.016 Uiso 1 1 calc R U . . .
H15B H 0.359057 0.835070 0.383392 0.016 Uiso 1 1 calc R U . . .
C16 C 0.32543(5) 0.5137(2) 0.35037(5) 0.0123(2) Uani 1 1 d . . . . .
C17 C 0.28539(5) 0.3332(2) 0.35616(5) 0.0160(2) Uani 1 1 d . . . . .
H17 H 0.265119 0.332729 0.388756 0.019 Uiso 1 1 calc R U . . .
C18 C 0.27477(5) 0.1546(2) 0.31504(6) 0.0191(3) Uani 1 1 d . . . . .
H18 H 0.247321 0.033611 0.319599 0.023 Uiso 1 1 calc R U . . .
C19 C 0.30423(6) 0.1524(2) 0.26718(6) 0.0205(3) Uani 1 1 d . . . . .
H19 H 0.297153 0.029964 0.239052 0.025 Uiso 1 1 calc R U . . .
C20 C 0.34407(6) 0.3308(2) 0.26085(5) 0.0197(3) Uani 1 1 d . . . . .
H20 H 0.364526 0.329639 0.228381 0.024 Uiso 1 1 calc R U . . .
C21 C 0.35420(5) 0.5115(2) 0.30193(5) 0.0165(2) Uani 1 1 d . . . . .
H21 H 0.381055 0.634597 0.296823 0.020 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 1.2366(14) . ?
C2 N3 1.3441(14) . ?
C2 C6 1.5113(16) . ?
N3 C4 1.4579(14) . ?
N3 H3 0.817(17) . ?
C4 C7 1.5405(16) . ?
C4 C5 1.5464(15) . ?
C4 H4 0.965(17) . ?
C5 C15 1.5375(16) . ?
C5 C6 1.5401(16) . ?
C5 H5 0.994(17) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C9 1.5080(16) . ?
C7 Cl8 1.8155(11) . ?
C7 H7 0.957(17) . ?
C9 C14 1.3902(17) . ?
C9 C10 1.3951(16) . ?
C10 C11 1.3896(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3967(18) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.5051(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C21 1.3929(16) . ?
C16 C17 1.3978(17) . ?
C17 C18 1.3881(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.3906(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.3878(19) . ?
C19 H19 0.9500 . ?
C20 C21 1.3937(18) . ?
C20 H20 0.9500 . ?
C21 H21 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 125.27(11) . . ?
O1 C2 C6 126.03(10) . . ?
N3 C2 C6 108.70(9) . . ?
C2 N3 C4 114.30(9) . . ?
C2 N3 H3 122.6(12) . . ?
C4 N3 H3 122.9(12) . . ?
N3 C4 C7 110.04(9) . . ?
N3 C4 C5 103.31(9) . . ?
C7 C4 C5 113.30(9) . . ?
N3 C4 H4 110.7(10) . . ?
C7 C4 H4 107.8(9) . . ?
C5 C4 H4 111.6(9) . . ?
C15 C5 C6 111.77(9) . . ?
C15 C5 C4 111.84(9) . . ?
C6 C5 C4 103.97(9) . . ?
C15 C5 H5 111.7(9) . . ?
C6 C5 H5 111.3(9) . . ?
C4 C5 H5 105.9(9) . . ?
C2 C6 C5 104.58(9) . . ?
C2 C6 H6A 110.8 . . ?
C5 C6 H6A 110.8 . . ?
C2 C6 H6B 110.8 . . ?
C5 C6 H6B 110.8 . . ?
H6A C6 H6B 108.9 . . ?
C9 C7 C4 113.15(9) . . ?
C9 C7 Cl8 111.00(8) . . ?
C4 C7 Cl8 106.41(8) . . ?
C9 C7 H7 107.9(9) . . ?
C4 C7 H7 112.9(10) . . ?
Cl8 C7 H7 105.2(10) . . ?
C14 C9 C10 119.61(11) . . ?
C14 C9 C7 118.72(10) . . ?
C10 C9 C7 121.54(11) . . ?
C11 C10 C9 120.01(13) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.21(12) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.30(13) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 119.58(13) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C9 C14 C13 120.29(12) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C5 111.31(9) . . ?
C16 C15 H15A 109.4 . . ?
C5 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C5 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C21 C16 C17 118.27(11) . . ?
C21 C16 C15 122.39(11) . . ?
C17 C16 C15 119.28(10) . . ?
C18 C17 C16 121.06(11) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 120.13(12) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 119.43(12) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 120.28(12) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C16 C21 C20 120.81(12) . . ?
C16 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
 
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
O1 C2 N3 C4 -176.52(11) . . . . ?
C6 C2 N3 C4 2.95(13) . . . . ?
C2 N3 C4 C7 105.06(11) . . . . ?
C2 N3 C4 C5 -16.19(12) . . . . ?
N3 C4 C5 C15 -98.84(10) . . . . ?
C7 C4 C5 C15 142.13(10) . . . . ?
N3 C4 C5 C6 21.93(11) . . . . ?
C7 C4 C5 C6 -97.11(10) . . . . ?
O1 C2 C6 C5 -168.79(11) . . . . ?
N3 C2 C6 C5 11.74(13) . . . . ?
C15 C5 C6 C2 100.19(11) . . . . ?
C4 C5 C6 C2 -20.61(11) . . . . ?
N3 C4 C7 C9 52.75(12) . . . . ?
C5 C4 C7 C9 167.83(9) . . . . ?
N3 C4 C7 Cl8 174.90(7) . . . . ?
C5 C4 C7 Cl8 -70.02(10) . . . . ?
C4 C7 C9 C14 -105.32(12) . . . . ?
Cl8 C7 C9 C14 135.13(10) . . . . ?
C4 C7 C9 C10 70.46(13) . . . . ?
Cl8 C7 C9 C10 -49.08(13) . . . . ?
C14 C9 C10 C11 0.38(17) . . . . ?
C7 C9 C10 C11 -175.37(11) . . . . ?
C9 C10 C11 C12 0.27(19) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C11 C12 C13 C14 -0.2(2) . . . . ?
C10 C9 C14 C13 -0.94(18) . . . . ?
C7 C9 C14 C13 174.93(11) . . . . ?
C12 C13 C14 C9 0.85(19) . . . . ?
C6 C5 C15 C16 68.37(12) . . . . ?
C4 C5 C15 C16 -175.52(9) . . . . ?
C5 C15 C16 C21 -103.12(13) . . . . ?
C5 C15 C16 C17 74.00(13) . . . . ?
C21 C16 C17 C18 0.57(18) . . . . ?
C15 C16 C17 C18 -176.68(11) . . . . ?
C16 C17 C18 C19 0.21(19) . . . . ?
C17 C18 C19 C20 -0.3(2) . . . . ?
C18 C19 C20 C21 -0.4(2) . . . . ?
C17 C16 C21 C20 -1.29(18) . . . . ?
C15 C16 C21 C20 175.86(11) . . . . ?
C19 C20 C21 C16 1.2(2) . . . . ?
 
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  0.817(17) 2.046(17) 2.8589(14) 173.2(17) 5_676 yes
 
_refine_diff_density_max    0.629
_refine_diff_density_min   -0.451
_refine_diff_density_rms    0.077





















