 
data_AX1852
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C22 H24 Cl N' 
_chemical_formula_weight          337.87

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0181   0.0091
 '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'   0.0311   0.0180
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl'  'Cl'   0.3639   0.7018
 '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                    6.4598(2)
_cell_length_b                    13.9948(3)
_cell_length_c                    21.6147(5)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1954.05(9)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     6135
_cell_measurement_theta_min       3.76
_cell_measurement_theta_max       66.26
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.148          
_exptl_crystal_F_000              720
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.281
_exptl_crystal_size_mid           0.148
_exptl_crystal_size_min           0.052
_exptl_absorpt_coefficient_mu     1.721
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.64
_exptl_absorpt_correction_T_max   0.92
_exptl_absorpt_process_details    'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_radiation_source          microfocus 
_diffrn_radiation_monochromator   multilayer
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  8.3333    
_diffrn_reflns_number             13628
_diffrn_reflns_av_unetI/netI      0.0313
_diffrn_reflns_av_R_equivalents   0.0364
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -25
_diffrn_reflns_limit_l_max        25
_diffrn_reflns_theta_min          3.763
_diffrn_reflns_theta_max          66.627
_diffrn_reflns_theta_full         66.627
_diffrn_measured_fraction_theta_max   1.000
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    1.000
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.999
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              3458
_reflns_number_gt                 3330
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.718
_reflns_Friedel_fraction_max      0.998
_reflns_Friedel_fraction_full     0.999
 
_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 (Bruker, 2014)' 
_computing_cell_refinement        'SAINT (Bruker, 2013)'
_computing_data_reduction         'SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement   'SHELXL-2014/7 (Sheldrick, 2015)'
_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)+(0.0586P)²+0.1566P] 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 1347 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    -0.013(7)
_chemical_absolute_configuration  ad
_refine_ls_number_reflns          3458
_refine_ls_number_parameters      214
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0352
_refine_ls_R_factor_gt            0.0336
_refine_ls_wR_factor_ref          0.0886
_refine_ls_wR_factor_gt           0.0873
_refine_ls_goodness_of_fit_ref    1.060
_refine_ls_restrained_S_all       1.060
_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
C1 C 0.5100(4) 0.28224(17) 0.36749(11) 0.0317(5) Uani 1 1 d . . . . .
H1C H 0.3589 0.2977 0.3663 0.038 Uiso 1 1 calc R U . . .
C2 C 0.5328(5) 0.17402(18) 0.37384(12) 0.0464(7) Uani 1 1 d . . . . .
H2A H 0.4727 0.1427 0.3375 0.070 Uiso 1 1 calc R U . . .
H2B H 0.4605 0.1525 0.4112 0.070 Uiso 1 1 calc R U . . .
H2C H 0.6799 0.1575 0.3769 0.070 Uiso 1 1 calc R U . . .
C3 C 0.6076(4) 0.31984(15) 0.30866(10) 0.0292(5) Uani 1 1 d . . . . .
C4 C 0.8101(4) 0.29902(19) 0.29228(11) 0.0349(5) Uani 1 1 d . . . . .
H4 H 0.8925 0.2602 0.3186 0.042 Uiso 1 1 calc R U . . .
C5 C 0.8933(4) 0.3343(2) 0.23783(12) 0.0434(6) Uani 1 1 d . . . . .
H5 H 1.0318 0.3189 0.2269 0.052 Uiso 1 1 calc R U . . .
C6 C 0.7766(6) 0.3916(2) 0.19933(12) 0.0488(7) Uani 1 1 d . . . . .
H6 H 0.8351 0.4166 0.1624 0.059 Uiso 1 1 calc R U . . .
C7 C 0.5751(6) 0.41229(18) 0.21479(12) 0.0465(7) Uani 1 1 d . . . . .
H7 H 0.4937 0.4511 0.1882 0.056 Uiso 1 1 calc R U . . .
C8 C 0.4899(4) 0.37666(18) 0.26918(11) 0.0361(5) Uani 1 1 d . . . . .
H8 H 0.3504 0.3912 0.2795 0.043 Uiso 1 1 calc R U . . .
C9 C 0.5359(4) 0.42736(15) 0.44134(10) 0.0287(5) Uani 1 1 d . . . . .
H9 H 0.3819 0.4278 0.4461 0.034 Uiso 1 1 calc R U . . .
C10 C 0.6314(4) 0.45102(17) 0.50478(10) 0.0329(5) Uani 1 1 d . . . . .
H10A H 0.5962 0.3996 0.5345 0.039 Uiso 1 1 calc R U . . .
H10B H 0.7840 0.4533 0.5008 0.039 Uiso 1 1 calc R U . . .
C11 C 0.5548(2) 0.54556(9) 0.52977(7) 0.0322(5) Uani 1 1 d G . . . .
C12 C 0.6852(2) 0.62455(11) 0.52914(8) 0.0421(6) Uani 1 1 d G . . . .
H12 H 0.8213 0.6190 0.5128 0.050 Uiso 1 1 calc R U . . .
C13 C 0.6166(3) 0.71159(9) 0.55235(8) 0.0581(9) Uani 1 1 d G . . . .
H13 H 0.7057 0.7656 0.5519 0.070 Uiso 1 1 calc R U . . .
C14 C 0.4175(4) 0.71965(10) 0.57619(8) 0.0621(10) Uani 1 1 d G . . . .
H14 H 0.3706 0.7791 0.5921 0.074 Uiso 1 1 calc R U . . .
C15 C 0.2870(3) 0.64066(13) 0.57683(8) 0.0571(8) Uani 1 1 d G . . . .
H15 H 0.1510 0.6462 0.5931 0.069 Uiso 1 1 calc R U . . .
C16 C 0.3557(2) 0.55362(11) 0.55362(8) 0.0417(6) Uani 1 1 d G . . . .
H16 H 0.2665 0.4996 0.5541 0.050 Uiso 1 1 calc R U . . .
C17 C 0.5920(4) 0.50040(15) 0.39236(10) 0.0290(5) Uani 1 1 d . . . . .
C18 C 0.7909(4) 0.50718(16) 0.36857(10) 0.0313(5) Uani 1 1 d . . . . .
H18 H 0.8967 0.4662 0.3836 0.038 Uiso 1 1 calc R U . . .
C19 C 0.8362(5) 0.57383(18) 0.32270(11) 0.0392(6) Uani 1 1 d . . . . .
H19 H 0.9717 0.5773 0.3058 0.047 Uiso 1 1 calc R U . . .
C20 C 0.6834(5) 0.63485(19) 0.30182(13) 0.0462(7) Uani 1 1 d . . . . .
H20 H 0.7138 0.6798 0.2702 0.055 Uiso 1 1 calc R U . . .
C21 C 0.4878(5) 0.63089(19) 0.32654(14) 0.0484(7) Uani 1 1 d . . . . .
H21 H 0.3847 0.6745 0.3129 0.058 Uiso 1 1 calc R U . . .
C22 C 0.4401(5) 0.56314(17) 0.37158(11) 0.0386(5) Uani 1 1 d . . . . .
H22 H 0.3039 0.5598 0.3881 0.046 Uiso 1 1 calc R U . . .
Cl1 Cl 0.56531(8) 0.19884(4) 0.54747(2) 0.03409(16) Uani 1 1 d . . . . .
N1 N 0.6007(3) 0.32671(13) 0.42528(8) 0.0276(4) Uani 1 1 d . . . . .
H1A H 0.744(4) 0.3220(19) 0.4234(12) 0.024(6) Uiso 1 1 d . . . . .
H1B H 0.563(5) 0.290(2) 0.4596(13) 0.037(7) Uiso 1 1 d . . . . .
 
 
_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
C1 N1 1.514(3) . ?
C1 C3 1.514(3) . ?
C1 C2 1.528(3) . ?
C1 H1C 1.0000 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.386(3) . ?
C3 C8 1.393(4) . ?
C4 C5 1.385(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.375(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 N1 1.510(3) . ?
C9 C17 1.516(3) . ?
C9 C10 1.540(3) . ?
C9 H9 1.0000 . ?
C10 C11 1.512(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.3900 . ?
C11 C16 1.3900 . ?
C12 C13 1.3900 . ?
C12 H12 0.9500 . ?
C13 C14 1.3900 . ?
C13 H13 0.9500 . ?
C14 C15 1.3900 . ?
C14 H14 0.9500 . ?
C15 C16 1.3900 . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.388(4) . ?
C17 C22 1.391(3) . ?
C18 C19 1.392(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.381(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.373(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.393(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
N1 H1A 0.93(3) . ?
N1 H1B 0.94(3) . ?
 
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
N1 C1 C3 112.89(18) . . ?
N1 C1 C2 107.22(19) . . ?
C3 C1 C2 112.32(19) . . ?
N1 C1 H1C 108.1 . . ?
C3 C1 H1C 108.1 . . ?
C2 C1 H1C 108.1 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 C8 118.6(2) . . ?
C4 C3 C1 122.3(2) . . ?
C8 C3 C1 119.0(2) . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C7 C6 C5 119.5(3) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 120.3(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C3 120.4(3) . . ?
C7 C8 H8 119.8 . . ?
C3 C8 H8 119.8 . . ?
N1 C9 C17 113.72(17) . . ?
N1 C9 C10 107.11(18) . . ?
C17 C9 C10 112.41(18) . . ?
N1 C9 H9 107.8 . . ?
C17 C9 H9 107.8 . . ?
C10 C9 H9 107.8 . . ?
C11 C10 C9 112.03(18) . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C16 120.0 . . ?
C12 C11 C10 119.59(14) . . ?
C16 C11 C10 120.41(14) . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.0 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 120.0 . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C18 C17 C22 119.4(2) . . ?
C18 C17 C9 121.8(2) . . ?
C22 C17 C9 118.8(2) . . ?
C17 C18 C19 120.3(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 119.8(3) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C21 C20 C19 120.4(2) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 120.2(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C17 C22 C21 119.9(3) . . ?
C17 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C9 N1 C1 117.76(18) . . ?
C9 N1 H1A 110.6(16) . . ?
C1 N1 H1A 108.8(16) . . ?
C9 N1 H1B 105.0(19) . . ?
C1 N1 H1B 109.1(19) . . ?
H1A N1 H1B 105(2) . . ?
 
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
N1 C1 C3 C4 69.2(3) . . . . ?
C2 C1 C3 C4 -52.2(3) . . . . ?
N1 C1 C3 C8 -111.4(2) . . . . ?
C2 C1 C3 C8 127.2(2) . . . . ?
C8 C3 C4 C5 0.2(3) . . . . ?
C1 C3 C4 C5 179.6(2) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 C7 -1.1(4) . . . . ?
C5 C6 C7 C8 0.7(4) . . . . ?
C6 C7 C8 C3 0.1(4) . . . . ?
C4 C3 C8 C7 -0.6(3) . . . . ?
C1 C3 C8 C7 180.0(2) . . . . ?
N1 C9 C10 C11 -172.62(17) . . . . ?
C17 C9 C10 C11 61.8(2) . . . . ?
C9 C10 C11 C12 -105.83(19) . . . . ?
C9 C10 C11 C16 74.6(2) . . . . ?
C16 C11 C12 C13 0.0 . . . . ?
C10 C11 C12 C13 -179.61(16) . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 C11 0.0 . . . . ?
C12 C11 C16 C15 0.0 . . . . ?
C10 C11 C16 C15 179.61(17) . . . . ?
N1 C9 C17 C18 -51.0(3) . . . . ?
C10 C9 C17 C18 71.0(3) . . . . ?
N1 C9 C17 C22 130.1(2) . . . . ?
C10 C9 C17 C22 -108.0(2) . . . . ?
C22 C17 C18 C19 -2.3(3) . . . . ?
C9 C17 C18 C19 178.7(2) . . . . ?
C17 C18 C19 C20 1.4(3) . . . . ?
C18 C19 C20 C21 0.8(4) . . . . ?
C19 C20 C21 C22 -2.1(4) . . . . ?
C18 C17 C22 C21 1.0(3) . . . . ?
C9 C17 C22 C21 -180.0(2) . . . . ?
C20 C21 C22 C17 1.1(4) . . . . ?
C17 C9 N1 C1 -60.9(2) . . . . ?
C10 C9 N1 C1 174.28(18) . . . . ?
C3 C1 N1 C9 76.0(2) . . . . ?
C2 C1 N1 C9 -159.7(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 
N1 H1A Cl1  0.93(3) 2.19(3) 3.079(2) 160(2) 4_556
N1 H1B Cl1  0.94(3) 2.29(3) 3.1984(19) 165(3) .
 
_refine_diff_density_max    0.331
_refine_diff_density_min   -0.180
_refine_diff_density_rms    0.041



