# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 1540656'
_audit_update_record             
;
2017-03-28 deposited with the CCDC.
2017-07-03 downloaded from the CCDC.
;
_chemical_name_systematic        4-pentyloxybenzylidene-4'-chloroaniline
_chemical_name_common            4-pentyloxybenzylidene-4'-chloroaniline
_chemical_formula_moiety         'C18 H20 Cl N O'
_chemical_formula_sum            'C18 H20 Cl N O'
_chemical_formula_iupac          'C18 H20 Cl N1 O1'
_chemical_formula_weight         301.81

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.3197(6)
_cell_length_b                   8.6990(2)
_cell_length_c                   9.8963(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.2801(15)
_cell_angle_gamma                90
_cell_volume                     1661.88(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4292
_cell_measurement_theta_min      1.0503
_cell_measurement_theta_max      22.8444
_cell_measurement_temperature    295.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.319
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640

_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      295.(2)

_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer optics'

_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            40074
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0118
_diffrn_reflns_theta_min         1.05
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_full        25.37
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             3045
_reflns_number_gt                2155
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1154
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_number_reflns         3045
_refine_ls_number_parameters     252
_refine_ls_number_restraints     3
_refine_ls_number_constraints    0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+0.3384P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.209
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 v2014.5-0 (Bruker AXS)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.12871(9) 0.50486(18) 0.0961(2) 0.0716(5) Uani d . . . 1.0 . .
C C2 0.09661(11) 0.3773(2) 0.0372(3) 0.0783(6) Uani d . . . 1.0 . .
C C3 0.06877(11) 0.3815(2) -0.0912(3) 0.0811(6) Uani d . . . 1.0 . .
C C4 0.06951(9) 0.5166(2) -0.1636(2) 0.0741(5) Uani d . . . 1.0 . .
C C5 0.09799(11) 0.6470(2) -0.1055(3) 0.0823(6) Uani d . . . 1.0 . .
C C6 0.12775(11) 0.6414(2) 0.0221(3) 0.0807(6) Uani d . . . 1.0 . .
C C7 0.21017(11) 0.5608(2) 0.2689(2) 0.0771(6) Uani d . . . 1.0 . .
C C8 0.23898(10) 0.54673(19) 0.4063(2) 0.0729(5) Uani d . . . 1.0 . .
C C9 0.30060(11) 0.6186(2) 0.4478(3) 0.0854(6) Uani d . . . 1.0 . .
C C10 0.32729(13) 0.6024(3) 0.5769(3) 0.0876(6) Uani d . . . 1.0 . .
C C11 0.29356(11) 0.51431(19) 0.6704(2) 0.0762(6) Uani d . . . 1.0 . .
C C12 0.23145(12) 0.4444(2) 0.6304(3) 0.0887(7) Uani d . . . 1.0 . .
C C13 0.20554(12) 0.4610(2) 0.5014(3) 0.0843(6) Uani d . . . 1.0 . .
C C14 0.29009(15) 0.4169(3) 0.8963(3) 0.1007(8) Uani d . . . 1.0 . .
C C15 0.33395(16) 0.4196(3) 1.0225(3) 0.1038(8) Uani d . . D 1.0 . .
C C16 0.40053(14) 0.3307(4) 1.0123(3) 0.0936(10) Uani d . P . 0.933(7) A 1
H H16A 0.4276 0.3769 0.9426 0.112 Uiso calc U P R 0.933(7) A 1
H H16B 0.3895 0.2264 0.9842 0.112 Uiso calc U P R 0.933(7) A 1
C C17 0.44428(19) 0.3247(5) 1.1424(3) 0.1322(14) Uani d . P . 0.933(7) A 1
H H17A 0.4561 0.4289 1.1696 0.159 Uiso calc U P R 0.933(7) A 1
H H17B 0.417 0.2801 1.2126 0.159 Uiso calc U P R 0.933(7) A 1
C C18 0.5092(2) 0.2346(5) 1.1322(4) 0.1876(17) Uani d . . D 1.0 . .
H H18A 0.5366 0.2777 1.0628 0.281 Uiso calc U . R 1.0 A 1
H H18B 0.498 0.1298 1.1102 0.281 Uiso calc U . R 1.0 A 1
H H18C 0.5349 0.2381 1.2172 0.281 Uiso calc U . R 1.0 A 1
C C16S 0.4138(11) 0.413(5) 1.052(6) 0.12(2) Uiso d . P D 0.067(7) A 2
H H16C 0.4381 0.4508 0.9746 0.149 Uiso calc U P R 0.067(7) A 2
H H16D 0.4266 0.4765 1.1296 0.149 Uiso calc U P R 0.067(7) A 2
C C17S 0.4331(12) 0.244(5) 1.080(5) 0.110(16) Uiso d . P D 0.067(7) A 2
H H17C 0.4267 0.1843 0.9981 0.132 Uiso calc U P R 0.067(7) A 2
H H17D 0.4031 0.2022 1.1475 0.132 Uiso calc U P R 0.067(7) A 2
Cl Cl1 0.03266(3) 0.52175(6) -0.32672(7) 0.0980(2) Uani d . . . 1.0 . .
H H1 0.0961(9) 0.289(2) 0.0902(18) 0.077(5) Uiso d . . . 1.0 . .
H H2 0.0481(10) 0.301(2) -0.1352(19) 0.086(6) Uiso d . . . 1.0 . .
H H3 0.0963(10) 0.737(2) -0.1551(19) 0.085(6) Uiso d . . . 1.0 . .
H H4 0.1467(9) 0.728(2) 0.0643(18) 0.080(6) Uiso d . . . 1.0 . .
H H5 0.2339(10) 0.628(2) 0.2096(18) 0.081(6) Uiso d . . . 1.0 . .
H H6 0.3240(11) 0.679(2) 0.383(2) 0.095(6) Uiso d . . . 1.0 . .
H H7 0.3683(11) 0.647(2) 0.6048(19) 0.091(7) Uiso d . . . 1.0 . .
H H8 0.2083(11) 0.389(2) 0.693(2) 0.094(6) Uiso d . . . 1.0 . .
H H9 0.1630(12) 0.415(3) 0.469(2) 0.103(7) Uiso d . . . 1.0 . .
H H10 0.2442(14) 0.464(3) 0.905(2) 0.119(8) Uiso d . . . 1.0 . .
H H11 0.2870(13) 0.304(3) 0.861(2) 0.126(9) Uiso d . . . 1.0 . .
H H12 0.3497(13) 0.523(3) 1.048(2) 0.119(9) Uiso d . . . 1.0 A 1
H H13 0.3099(13) 0.371(3) 1.098(3) 0.132(9) Uiso d . . . 1.0 A 1
N N1 0.15672(9) 0.48753(16) 0.22832(19) 0.0780(5) Uani d . . . 1.0 . .
O O1 0.32451(8) 0.50449(15) 0.79564(17) 0.0894(4) Uani d . . . 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.388(3) ?
C1 C6 . 1.396(3) ?
C1 N1 . 1.404(3) ?
C2 C3 . 1.360(3) ?
C2 H1 . 0.93(2) ?
C3 C4 . 1.377(3) ?
C3 H2 . 0.91(2) ?
C4 C5 . 1.377(3) ?
C4 Cl1 . 1.739(2) ?
C5 C6 . 1.367(3) ?
C5 H3 . 0.92(2) ?
C6 H4 . 0.93(2) ?
C7 N1 . 1.265(3) ?
C7 C8 . 1.454(3) ?
C7 H5 . 0.96(2) ?
C8 C13 . 1.381(3) ?
C8 C9 . 1.392(3) ?
C9 C10 . 1.366(3) ?
C9 H6 . 0.95(2) ?
C10 C11 . 1.384(3) ?
C10 H7 . 0.92(2) ?
C11 O1 . 1.357(3) ?
C11 C12 . 1.389(3) ?
C12 C13 . 1.360(3) ?
C12 H8 . 0.92(2) ?
C13 H9 . 0.96(2) ?
C14 O1 . 1.438(3) ?
C14 C15 . 1.481(4) ?
C14 H10 . 0.98(3) ?
C14 H11 . 1.04(3) ?
C15 C16 . 1.508(4) ?
C15 C16S . 1.560(19) ?
C15 H12 . 0.98(3) ?
C15 H13 . 0.99(3) ?
C16 C17 . 1.512(4) ?
C16 H16A . 0.97 ?
C16 H16B . 0.97 ?
C17 C18 . 1.485(5) ?
C17 H17A . 0.97 ?
C17 H17B . 0.97 ?
C18 C17S . 1.540(19) ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
C16S C17S . 1.54(2) ?
C16S H16C . 0.97 ?
C16S H16D . 0.97 ?
C17S H17C . 0.97 ?
C17S H17D . 0.97 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 117.6(2) ?
C2 C1 N1 . . 117.07(18) ?
C6 C1 N1 . . 125.28(19) ?
C3 C2 C1 . . 121.6(2) ?
C3 C2 H1 . . 122.4(11) ?
C1 C2 H1 . . 115.9(12) ?
C2 C3 C4 . . 119.8(2) ?
C2 C3 H2 . . 125.3(13) ?
C4 C3 H2 . . 114.9(13) ?
C3 C4 C5 . . 119.9(2) ?
C3 C4 Cl1 . . 119.53(17) ?
C5 C4 Cl1 . . 120.56(17) ?
C6 C5 C4 . . 120.2(2) ?
C6 C5 H3 . . 121.8(12) ?
C4 C5 H3 . . 118.0(12) ?
C5 C6 C1 . . 120.8(2) ?
C5 C6 H4 . . 122.1(12) ?
C1 C6 H4 . . 117.1(12) ?
N1 C7 C8 . . 122.12(19) ?
N1 C7 H5 . . 121.1(11) ?
C8 C7 H5 . . 116.7(11) ?
C13 C8 C9 . . 117.4(2) ?
C13 C8 C7 . . 120.7(2) ?
C9 C8 C7 . . 121.92(19) ?
C10 C9 C8 . . 121.1(2) ?
C10 C9 H6 . . 120.8(12) ?
C8 C9 H6 . . 118.2(12) ?
C9 C10 C11 . . 120.8(2) ?
C9 C10 H7 . . 121.8(13) ?
C11 C10 H7 . . 117.4(13) ?
O1 C11 C10 . . 116.3(2) ?
O1 C11 C12 . . 125.28(19) ?
C10 C11 C12 . . 118.4(3) ?
C13 C12 C11 . . 120.2(2) ?
C13 C12 H8 . . 121.4(13) ?
C11 C12 H8 . . 118.4(13) ?
C12 C13 C8 . . 122.2(2) ?
C12 C13 H9 . . 122.9(13) ?
C8 C13 H9 . . 114.9(14) ?
O1 C14 C15 . . 108.1(2) ?
O1 C14 H10 . . 106.8(14) ?
C15 C14 H10 . . 113.8(14) ?
O1 C14 H11 . . 106.9(14) ?
C15 C14 H11 . . 108.5(14) ?
H10 C14 H11 . . 112.(2) ?
C14 C15 C16 . . 113.4(2) ?
C14 C15 C16S . . 133.(2) ?
C14 C15 H12 . . 113.1(15) ?
C16 C15 H12 . . 103.3(15) ?
C14 C15 H13 . . 111.2(15) ?
C16 C15 H13 . . 105.1(15) ?
H12 C15 H13 . . 110.(2) ?
C15 C16 C17 . . 114.2(3) ?
C15 C16 H16A . . 108.7 ?
C17 C16 H16A . . 108.7 ?
C15 C16 H16B . . 108.7 ?
C17 C16 H16B . . 108.7 ?
H16A C16 H16B . . 107.6 ?
C18 C17 C16 . . 113.9(3) ?
C18 C17 H17A . . 108.8 ?
C16 C17 H17A . . 108.8 ?
C18 C17 H17B . . 108.8 ?
C16 C17 H17B . . 108.8 ?
H17A C17 H17B . . 107.7 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C17S C16S C15 . . 107.(2) ?
C17S C16S H16C . . 110.2 ?
C15 C16S H16C . . 110.2 ?
C17S C16S H16D . . 110.2 ?
C15 C16S H16D . . 110.2 ?
H16C C16S H16D . . 108.5 ?
C16S C17S C18 . . 109.(2) ?
C16S C17S H17C . . 109.8 ?
C18 C17S H17C . . 109.8 ?
C16S C17S H17D . . 109.8 ?
C18 C17S H17D . . 109.8 ?
H17C C17S H17D . . 108.2 ?
C7 N1 C1 . . 121.41(18) ?
C11 O1 C14 . . 117.83(19) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 3.9(3) ?
N1 C1 C2 C3 . . . . -179.01(17) ?
C1 C2 C3 C4 . . . . -2.7(3) ?
C2 C3 C4 C5 . . . . -0.4(3) ?
C2 C3 C4 Cl1 . . . . -179.06(15) ?
C3 C4 C5 C6 . . . . 2.4(3) ?
Cl1 C4 C5 C6 . . . . -179.04(15) ?
C4 C5 C6 C1 . . . . -1.1(3) ?
C2 C1 C6 C5 . . . . -1.9(3) ?
N1 C1 C6 C5 . . . . -178.77(17) ?
N1 C7 C8 C13 . . . . -5.1(3) ?
N1 C7 C8 C9 . . . . 175.15(18) ?
C13 C8 C9 C10 . . . . 1.1(3) ?
C7 C8 C9 C10 . . . . -179.20(19) ?
C8 C9 C10 C11 . . . . -0.2(3) ?
C9 C10 C11 O1 . . . . 179.50(18) ?
C9 C10 C11 C12 . . . . -0.9(3) ?
O1 C11 C12 C13 . . . . -179.37(18) ?
C10 C11 C12 C13 . . . . 1.0(3) ?
C11 C12 C13 C8 . . . . -0.1(3) ?
C9 C8 C13 C12 . . . . -0.9(3) ?
C7 C8 C13 C12 . . . . 179.36(18) ?
O1 C14 C15 C16 . . . . -68.7(3) ?
O1 C14 C15 C16S . . . . -38.(2) ?
C14 C15 C16 C17 . . . . -176.8(3) ?
C15 C16 C17 C18 . . . . 179.0(3) ?
C14 C15 C16S C17S . . . . -95.(4) ?
C15 C16S C17S C18 . . . . -171.(3) ?
C8 C7 N1 C1 . . . . 178.65(15) ?
C2 C1 N1 C7 . . . . 147.96(18) ?
C6 C1 N1 C7 . . . . -35.2(3) ?
C10 C11 O1 C14 . . . . 178.5(2) ?
C12 C11 O1 C14 . . . . -1.1(3) ?
C15 C14 O1 C11 . . . . 178.70(19) ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 1540655'
_audit_update_record             
;
2017-03-28 deposited with the CCDC.
2017-07-03 downloaded from the CCDC.
;
_chemical_name_systematic        4-chlorobenzylidene-4'-pentyloxyaniline
_chemical_name_common            4-chlorobenzylidene-4'-pentyloxyaniline
_chemical_formula_moiety         'C18 H20 Cl N O'
_chemical_formula_sum            'C18 H20 Cl N O'
_chemical_formula_iupac          'C18 H20 Cl N1 O1'
_chemical_formula_weight         301.81
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   6.1002(3)
_cell_length_b                   7.3335(4)
_cell_length_c                   36.4538(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1630.79(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3922
_cell_measurement_theta_min      1.1029
_cell_measurement_theta_max      22.7969
_cell_measurement_temperature    295.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.305
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640

_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      295.(2)

_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer optics'

_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            10115
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_theta_min         1.12
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       47

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             3309
_reflns_number_gt                2553
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1128
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_number_reflns         3309
_refine_ls_number_parameters     259
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0584P)²+0.0894P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.112
_refine_diff_density_min         -0.144
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 914 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(5)

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 v2014.5-0 (Bruker AXS)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4918(5) 0.7525(4) 0.11605(9) 0.0463(7) Uani d . . . 1 . .
C C2 0.2826(6) 0.8141(5) 0.10809(10) 0.0546(8) Uani d . . . 1 . .
C C3 0.2083(6) 0.8182(5) 0.07239(11) 0.0615(9) Uani d . . . 1 . .
C C4 0.3415(7) 0.7594(5) 0.04472(10) 0.0628(9) Uani d . . . 1 . .
C C5 0.5477(7) 0.6910(6) 0.05198(11) 0.0685(10) Uani d . . . 1 . .
C C6 0.6232(6) 0.6883(5) 0.08762(10) 0.0571(8) Uani d . . . 1 . .
C C7 0.5715(6) 0.7609(4) 0.15410(9) 0.0477(7) Uani d . . . 1 . .
C C8 0.8364(5) 0.7466(3) 0.19971(8) 0.0409(6) Uani d . . . 1 . .
C C9 1.0328(5) 0.6610(4) 0.20894(8) 0.0425(6) Uani d . . . 1 . .
C C10 1.1144(5) 0.6627(3) 0.24430(8) 0.0422(6) Uani d . . . 1 . .
C C11 0.9989(5) 0.7552(3) 0.27152(8) 0.0407(7) Uani d . . . 1 . .
C C12 0.8033(5) 0.8424(4) 0.26244(9) 0.0438(6) Uani d . . . 1 . .
C C13 0.7234(5) 0.8388(4) 0.22739(9) 0.0451(7) Uani d . . . 1 . .
C C14 1.2726(6) 0.7058(5) 0.31816(10) 0.0510(7) Uani d . . . 1 . .
C C15 1.3165(6) 0.7819(5) 0.35561(11) 0.0583(8) Uani d . . . 1 . .
C C16 1.5223(7) 0.7103(6) 0.37383(11) 0.0608(9) Uani d . . . 1 . .
C C17 1.5557(9) 0.7863(6) 0.41180(12) 0.0715(11) Uani d . . . 1 . .
C C18 1.7474(9) 0.7081(8) 0.43235(15) 0.0973(16) Uani d . . . 1 . .
H H18A 1.7251 0.5798 0.436 0.146 Uiso calc U . R 1 . .
H H18B 1.7603 0.7676 0.4557 0.146 Uiso calc U . R 1 . .
H H18C 1.8791 0.727 0.4185 0.146 Uiso calc U . R 1 . .
Cl Cl1 0.2463(3) 0.7644(2) 0.00000(4) 0.1108(5) Uani d . . . 1 . .
H H1 0.192(6) 0.840(5) 0.1299(11) 0.062(10) Uiso d . . . 1 . .
H H2 0.071(7) 0.861(5) 0.0685(11) 0.070(10) Uiso d . . . 1 . .
H H3 0.626(8) 0.642(6) 0.0322(14) 0.094(14) Uiso d . . . 1 . .
H H4 0.762(6) 0.623(5) 0.0932(11) 0.076(11) Uiso d . . . 1 . .
H H5 0.441(8) 0.779(5) 0.1732(13) 0.083(13) Uiso d . . . 1 . .
H H6 1.110(5) 0.597(3) 0.1896(8) 0.035(6) Uiso d . . . 1 . .
H H7 1.248(5) 0.596(4) 0.2504(10) 0.055(8) Uiso d . . . 1 . .
H H8 0.729(5) 0.907(4) 0.2806(9) 0.052(9) Uiso d . . . 1 . .
H H9 0.591(6) 0.889(5) 0.2229(9) 0.054(9) Uiso d . . . 1 . .
H H10 1.377(6) 0.739(4) 0.3003(10) 0.049(9) Uiso d . . . 1 . .
H H11 1.273(5) 0.571(4) 0.3180(9) 0.053(8) Uiso d . . . 1 . .
H H12 1.188(9) 0.741(5) 0.3734(16) 0.096(16) Uiso d . . . 1 . .
H H13 1.314(6) 0.914(5) 0.3555(10) 0.072(10) Uiso d . . . 1 . .
H H14 1.652(7) 0.738(5) 0.3569(12) 0.062(11) Uiso d . . . 1 . .
H H15 1.510(6) 0.580(5) 0.3741(11) 0.067(10) Uiso d . . . 1 . .
H H16 1.432(8) 0.761(5) 0.4269(16) 0.080(14) Uiso d . . . 1 . .
H H17 1.564(6) 0.915(5) 0.4109(10) 0.074(11) Uiso d . . . 1 . .
N N1 0.7687(4) 0.7344(3) 0.16256(8) 0.0473(6) Uani d . . . 1 . .
O O1 1.0619(4) 0.7732(3) 0.30722(6) 0.0515(5) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.385(5) ?
C1 C6 . 1.392(5) ?
C1 C7 . 1.471(5) ?
C2 C3 . 1.378(5) ?
C2 H1 . 0.99(4) ?
C3 C4 . 1.365(6) ?
C3 H2 . 0.91(4) ?
C4 C5 . 1.380(6) ?
C4 Cl1 . 1.731(4) ?
C5 C6 . 1.378(6) ?
C5 H3 . 0.94(5) ?
C6 H4 . 0.99(4) ?
C7 N1 . 1.257(4) ?
C7 H5 . 1.07(5) ?
C8 C9 . 1.394(4) ?
C8 C13 . 1.397(4) ?
C8 N1 . 1.419(4) ?
C9 C10 . 1.382(4) ?
C9 H6 . 0.97(3) ?
C10 C11 . 1.393(4) ?
C10 H7 . 0.98(3) ?
C11 O1 . 1.363(4) ?
C11 C12 . 1.393(4) ?
C12 C13 . 1.368(4) ?
C12 H8 . 0.93(3) ?
C13 H9 . 0.90(4) ?
C14 O1 . 1.434(4) ?
C14 C15 . 1.499(5) ?
C14 H10 . 0.94(4) ?
C14 H11 . 0.99(3) ?
C15 C16 . 1.515(5) ?
C15 H12 . 1.06(5) ?
C15 H13 . 0.97(4) ?
C16 C17 . 1.506(6) ?
C16 H14 . 1.02(4) ?
C16 H15 . 0.96(4) ?
C17 C18 . 1.502(7) ?
C17 H16 . 0.95(5) ?
C17 H17 . 0.94(4) ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 119.0(3) ?
C2 C1 C7 . . 119.2(3) ?
C6 C1 C7 . . 121.8(3) ?
C3 C2 C1 . . 120.5(4) ?
C3 C2 H1 . . 125.(2) ?
C1 C2 H1 . . 114.(2) ?
C4 C3 C2 . . 119.7(4) ?
C4 C3 H2 . . 123.(3) ?
C2 C3 H2 . . 117.(3) ?
C3 C4 C5 . . 121.0(4) ?
C3 C4 Cl1 . . 119.3(3) ?
C5 C4 Cl1 . . 119.6(3) ?
C6 C5 C4 . . 119.4(4) ?
C6 C5 H3 . . 123.(3) ?
C4 C5 H3 . . 117.(3) ?
C5 C6 C1 . . 120.3(3) ?
C5 C6 H4 . . 119.(2) ?
C1 C6 H4 . . 120.(2) ?
N1 C7 C1 . . 122.7(3) ?
N1 C7 H5 . . 125.(3) ?
C1 C7 H5 . . 112.(3) ?
C9 C8 C13 . . 117.9(3) ?
C9 C8 N1 . . 116.9(3) ?
C13 C8 N1 . . 125.2(3) ?
C10 C9 C8 . . 122.1(3) ?
C10 C9 H6 . . 120.5(16) ?
C8 C9 H6 . . 117.4(16) ?
C9 C10 C11 . . 119.1(3) ?
C9 C10 H7 . . 121.(2) ?
C11 C10 H7 . . 120.(2) ?
O1 C11 C10 . . 125.8(3) ?
O1 C11 C12 . . 115.0(3) ?
C10 C11 C12 . . 119.2(3) ?
C13 C12 C11 . . 121.2(3) ?
C13 C12 H8 . . 120.(2) ?
C11 C12 H8 . . 119.(2) ?
C12 C13 C8 . . 120.6(3) ?
C12 C13 H9 . . 119.(2) ?
C8 C13 H9 . . 121.(2) ?
O1 C14 C15 . . 106.6(3) ?
O1 C14 H10 . . 109.(2) ?
C15 C14 H10 . . 115.(2) ?
O1 C14 H11 . . 110.3(18) ?
C15 C14 H11 . . 112.2(19) ?
H10 C14 H11 . . 104.(2) ?
C14 C15 C16 . . 114.7(3) ?
C14 C15 H12 . . 109.(3) ?
C16 C15 H12 . . 104.(3) ?
C14 C15 H13 . . 111.(2) ?
C16 C15 H13 . . 111.(2) ?
H12 C15 H13 . . 106.(3) ?
C17 C16 C15 . . 112.8(4) ?
C17 C16 H14 . . 112.(2) ?
C15 C16 H14 . . 108.(2) ?
C17 C16 H15 . . 112.(2) ?
C15 C16 H15 . . 107.(2) ?
H14 C16 H15 . . 105.(3) ?
C18 C17 C16 . . 115.0(4) ?
C18 C17 H16 . . 105.(3) ?
C16 C17 H16 . . 111.(3) ?
C18 C17 H17 . . 111.(2) ?
C16 C17 H17 . . 110.(2) ?
H16 C17 H17 . . 105.(3) ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C7 N1 C8 . . 120.2(3) ?
C11 O1 C14 . . 119.0(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -2.4(5) ?
C7 C1 C2 C3 . . . . 176.1(3) ?
C1 C2 C3 C4 . . . . 0.6(5) ?
C2 C3 C4 C5 . . . . 1.8(5) ?
C2 C3 C4 Cl1 . . . . 179.8(3) ?
C3 C4 C5 C6 . . . . -2.4(6) ?
Cl1 C4 C5 C6 . . . . 179.6(3) ?
C4 C5 C6 C1 . . . . 0.6(6) ?
C2 C1 C6 C5 . . . . 1.8(5) ?
C7 C1 C6 C5 . . . . -176.6(3) ?
C2 C1 C7 N1 . . . . -168.7(3) ?
C6 C1 C7 N1 . . . . 9.6(4) ?
C13 C8 C9 C10 . . . . 1.2(4) ?
N1 C8 C9 C10 . . . . -179.6(3) ?
C8 C9 C10 C11 . . . . -1.1(4) ?
C9 C10 C11 O1 . . . . -178.0(2) ?
C9 C10 C11 C12 . . . . 0.5(4) ?
O1 C11 C12 C13 . . . . 178.5(3) ?
C10 C11 C12 C13 . . . . -0.1(4) ?
C11 C12 C13 C8 . . . . 0.2(4) ?
C9 C8 C13 C12 . . . . -0.7(4) ?
N1 C8 C13 C12 . . . . -179.9(3) ?
O1 C14 C15 C16 . . . . 173.9(3) ?
C14 C15 C16 C17 . . . . -178.3(4) ?
C15 C16 C17 C18 . . . . 175.2(4) ?
C1 C7 N1 C8 . . . . 179.2(3) ?
C9 C8 N1 C7 . . . . 159.9(3) ?
C13 C8 N1 C7 . . . . -20.8(4) ?
C10 C11 O1 C14 . . . . 5.4(4) ?
C12 C11 O1 C14 . . . . -173.1(3) ?
C15 C14 O1 C11 . . . . 167.2(3) ?


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 1540657'
_audit_update_record             
;
2017-03-28 deposited with the CCDC.
2017-07-03 downloaded from the CCDC.
;
_chemical_name_systematic        4-pentyloxybenzylidene-4'-chloroaniline
_chemical_name_common            4-pentyloxybenzylidene-4'-chloroaniline

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H20 Cl N O'
_chemical_formula_moiety         'C18 H20 Cl N O'
_chemical_formula_weight         301.81
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   18.4072(7)
_cell_length_b                   8.61246(16)
_cell_length_c                   9.9664(2)
_cell_angle_alpha                93.7782(16)
_cell_angle_beta                 90.5052(14)
_cell_angle_gamma                95.6436(10)
_cell_volume                     1568.73(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4530
_cell_measurement_theta_min      4.45
_cell_measurement_theta_max      68.09
_cell_measurement_temperature    106(1)
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640.00
_exptl_absorpt_coefficient_mu    2.129
_exptl_absorpt_correction_type   none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      106(1)
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     1.5412
_diffrn_radiation_monochromator  'Si 111'
_diffrn_measurement_device_type  'KEK UNIAXIS goniometer - IPDSC scanner'
_diffrn_measurement_method       'Ω scans'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            6530
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_theta_max         68.214
_diffrn_reflns_theta_min         4.445
_diffrn_reflns_theta_full        67.626
_diffrn_measured_fraction_theta_max 0.505
_diffrn_measured_fraction_theta_full 0.508
_diffrn_reflns_Laue_measured_fraction_max 0.505
_diffrn_reflns_Laue_measured_fraction_full 0.508
_diffrn_reflns_point_group_measured_fraction_max 0.505
_diffrn_reflns_point_group_measured_fraction_full 0.508
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_reflns_number_total             6530
_reflns_number_gt                5573
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;Refined as a 2-component twin.
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt)., Twin
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0786
_refine_ls_wR_factor_ref         0.2983
_refine_ls_wR_factor_gt          0.2945
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6530
_refine_ls_number_parameters     382
_refine_ls_goodness_of_fit_ref   1.246
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1133P)²+4.7614P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.432
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.1321(5) 0.5321(9) 0.0917(16) 0.045(5) Uani 1 1 d . . . . .
C2 C 0.0975(5) 0.3959(9) 0.0285(16) 0.052(6) Uani 1 1 d . . . . .
H1 H 0.094230 0.301518 0.073265 0.062 Uiso 1 1 calc R U . . .
C3 C 0.0679(5) 0.3967(9) -0.0987(16) 0.044(6) Uani 1 1 d . . . . .
H2 H 0.044560 0.303358 -0.142251 0.053 Uiso 1 1 calc R U . . .
C4 C 0.0725(5) 0.5357(10) -0.1624(15) 0.051(5) Uani 1 1 d . . . . .
C5 C 0.1022(5) 0.6747(10) -0.0988(16) 0.055(6) Uani 1 1 d . . . . .
H3 H 0.100452 0.770293 -0.140623 0.066 Uiso 1 1 calc R U . . .
C6 C 0.1342(5) 0.6728(9) 0.0252(16) 0.055(6) Uani 1 1 d . . . . .
H4 H 0.157945 0.766632 0.067245 0.066 Uiso 1 1 calc R U . . .
C7 C 0.2198(5) 0.6025(9) 0.2657(16) 0.049(6) Uani 1 1 d . . . . .
H5 H 0.245101 0.672856 0.208553 0.059 Uiso 1 1 calc R U . . .
C8 C 0.2482(5) 0.5893(10) 0.4016(17) 0.045(5) Uani 1 1 d . . . . .
C9 C 0.3165(5) 0.6661(10) 0.4399(17) 0.054(6) Uani 1 1 d . . . . .
H6 H 0.343931 0.728346 0.379283 0.065 Uiso 1 1 calc R U . . .
C10 C 0.3436(6) 0.6492(10) 0.5696(17) 0.048(6) Uani 1 1 d . . . . .
H7 H 0.390077 0.700014 0.596909 0.058 Uiso 1 1 calc R U . . .
C11 C 0.3033(6) 0.5589(10) 0.6586(17) 0.047(6) Uani 1 1 d . . . . .
C12 C 0.2343(6) 0.4846(10) 0.6185(16) 0.044(5) Uani 1 1 d . . . . .
H8 H 0.205299 0.424713 0.678633 0.053 Uiso 1 1 calc R U . . .
C13 C 0.2100(6) 0.5014(10) 0.4889(17) 0.047(6) Uani 1 1 d . . . . .
H9 H 0.164195 0.448571 0.460226 0.056 Uiso 1 1 calc R U . . .
C14 C 0.2893(5) 0.4629(10) 0.8774(16) 0.054(6) Uani 1 1 d . . . . .
H14A H 0.274360 0.354723 0.840865 0.065 Uiso 1 1 calc R U . . .
H14B H 0.244795 0.515832 0.896236 0.065 Uiso 1 1 calc R U . . .
C15 C 0.3335(5) 0.4606(9) 1.0039(15) 0.052(5) Uani 1 1 d . . . . .
H15A H 0.301046 0.420208 1.075015 0.062 Uiso 1 1 calc R U . . .
H15B H 0.352272 0.569313 1.033188 0.062 Uiso 1 1 calc R U . . .
C16 C 0.3975(5) 0.3627(10) 0.9918(14) 0.047(5) Uani 1 1 d . . . . .
H16A H 0.379756 0.256827 0.952978 0.056 Uiso 1 1 calc R U . . .
H16B H 0.433022 0.410116 0.928524 0.056 Uiso 1 1 calc R U . . .
C17 C 0.4362(5) 0.3477(11) 1.1241(14) 0.049(5) Uani 1 1 d . . . . .
H17A H 0.400478 0.304189 1.188805 0.058 Uiso 1 1 calc R U . . .
H17B H 0.456146 0.452915 1.161099 0.058 Uiso 1 1 calc R U . . .
C18 C 0.4981(5) 0.2431(11) 1.1099(15) 0.052(5) Uani 1 1 d . . . . .
H18A H 0.478292 0.136922 1.078992 0.063 Uiso 1 1 calc R U . . .
H18B H 0.522777 0.240895 1.197246 0.063 Uiso 1 1 calc R U . . .
H18C H 0.533165 0.284290 1.044459 0.063 Uiso 1 1 calc R U . . .
Cl1 Cl 0.03395(13) 0.5357(2) -0.3250(4) 0.0563(16) Uani 1 1 d . . . . .
N1 N 0.1605(4) 0.5193(7) 0.2219(13) 0.051(5) Uani 1 1 d . . . . .
O1 O 0.3338(4) 0.5462(7) 0.7811(11) 0.050(4) Uani 1 1 d . . . . .
C19 C 0.1320(5) 0.0176(9) 0.5924(16) 0.042(5) Uani 1 1 d . . . . .
C20 C 0.1013(5) 0.1465(9) 0.5431(16) 0.047(6) Uani 1 1 d . . . . .
H21 H 0.101010 0.240302 0.598740 0.057 Uiso 1 1 calc R U . . .
C21 C 0.0719(5) 0.1384(9) 0.4164(16) 0.047(6) Uani 1 1 d . . . . .
H22 H 0.052062 0.226655 0.383797 0.056 Uiso 1 1 calc R U . . .
C22 C 0.0712(5) 0.0012(10) 0.3355(15) 0.054(5) Uani 1 1 d . . . . .
C23 C 0.0976(5) -0.1305(10) 0.3845(16) 0.056(6) Uani 1 1 d . . . . .
H23 H 0.093972 -0.226271 0.330798 0.067 Uiso 1 1 calc R U . . .
C24 C 0.1283(5) -0.1217(10) 0.5087(17) 0.063(6) Uani 1 1 d . . . . .
H24 H 0.147797 -0.210916 0.540265 0.075 Uiso 1 1 calc R U . . .
C25 C 0.2172(5) -0.0311(9) 0.7567(16) 0.047(5) Uani 1 1 d . . . . .
H25 H 0.240149 -0.094332 0.691336 0.056 Uiso 1 1 calc R U . . .
C26 C 0.2453(5) -0.0133(9) 0.8951(16) 0.036(5) Uani 1 1 d . . . . .
C27 C 0.3076(5) -0.0855(9) 0.9296(17) 0.052(6) Uani 1 1 d . . . . .
H26 H 0.331078 -0.146729 0.863618 0.062 Uiso 1 1 calc R U . . .
C28 C 0.3338(6) -0.0669(9) 1.0583(17) 0.052(6) Uani 1 1 d . . . . .
H27 H 0.376120 -0.114866 1.081047 0.062 Uiso 1 1 calc R U . . .
C29 C 0.2995(5) 0.0222(9) 1.1590(18) 0.053(6) Uani 1 1 d . . . . .
C30 C 0.2380(5) 0.0926(10) 1.1248(16) 0.043(5) Uani 1 1 d . . . . .
H28 H 0.214243 0.153701 1.190610 0.051 Uiso 1 1 calc R U . . .
C31 C 0.2114(5) 0.0727(9) 0.9928(18) 0.053(6) Uani 1 1 d . . . . .
H29 H 0.168834 0.119665 0.969707 0.064 Uiso 1 1 calc R U . . .
C32 C 0.2966(5) 0.1281(10) 1.3893(16) 0.058(6) Uani 1 1 d . . . . .
H32A H 0.249228 0.072900 1.413272 0.070 Uiso 1 1 calc R U . . .
H32B H 0.287739 0.231806 1.358750 0.070 Uiso 1 1 calc R U . . .
C33 C 0.3485(5) 0.1468(10) 1.5098(15) 0.055(6) Uani 1 1 d . . . . .
H33A H 0.323308 0.193335 1.587706 0.066 Uiso 1 1 calc R U . . .
H33B H 0.360271 0.041869 1.532642 0.066 Uiso 1 1 calc R U . . .
C34 C 0.4188(5) 0.2468(10) 1.4890(15) 0.057(6) Uani 1 1 d . . . . .
H34A H 0.407279 0.342826 1.447311 0.069 Uiso 1 1 calc R U . . .
H34B H 0.448924 0.189137 1.424989 0.069 Uiso 1 1 calc R U . . .
C35 C 0.4634(6) 0.2935(11) 1.6168(15) 0.062(6) Uani 1 1 d . . . . .
H35A H 0.433483 0.353231 1.679684 0.075 Uiso 1 1 calc R U . . .
H35B H 0.506473 0.364488 1.594026 0.075 Uiso 1 1 calc R U . . .
C36 C 0.4899(6) 0.1581(12) 1.6893(15) 0.067(6) Uani 1 1 d . . . . .
H36A H 0.448231 0.099193 1.729277 0.081 Uiso 1 1 calc R U . . .
H36B H 0.525102 0.199527 1.760308 0.081 Uiso 1 1 calc R U . . .
H36C H 0.513419 0.088890 1.624880 0.081 Uiso 1 1 calc R U . . .
Cl2 Cl 0.03279(13) -0.0072(2) 0.1723(4) 0.0574(16) Uani 1 1 d . . . . .
N2 N 0.1613(4) 0.0383(7) 0.7223(13) 0.046(4) Uani 1 1 d . . . . .
O2 O 0.3314(4) 0.0368(7) 1.2829(11) 0.055(4) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2016/6 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C2 1.389(13) . ?
C1 N1 1.410(16) . ?
C1 C6 1.416(14) . ?
C2 C3 1.375(17) . ?
C2 H1 0.9500 . ?
C3 C4 1.387(14) . ?
C3 H2 0.9500 . ?
C4 C5 1.377(13) . ?
C4 Cl1 1.763(14) . ?
C5 C6 1.367(17) . ?
C5 H3 0.9500 . ?
C6 H4 0.9500 . ?
C7 N1 1.301(11) . ?
C7 C8 1.463(18) . ?
C7 H5 0.9500 . ?
C8 C13 1.349(18) . ?
C8 C9 1.399(13) . ?
C9 C10 1.404(18) . ?
C9 H6 0.9500 . ?
C10 C11 1.389(18) . ?
C10 H7 0.9500 . ?
C11 O1 1.355(15) . ?
C11 C12 1.407(13) . ?
C12 C13 1.385(17) . ?
C12 H8 0.9500 . ?
C13 H9 0.9500 . ?
C14 O1 1.447(15) . ?
C14 C15 1.497(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.515(12) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.513(15) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.522(13) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 N2 1.392(16) . ?
C19 C20 1.409(12) . ?
C19 C24 1.411(16) . ?
C20 C21 1.363(17) . ?
C20 H21 0.9500 . ?
C21 C22 1.385(15) . ?
C21 H22 0.9500 . ?
C22 C23 1.392(13) . ?
C22 Cl2 1.762(14) . ?
C23 C24 1.351(18) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 N2 1.294(11) . ?
C25 C26 1.463(17) . ?
C25 H25 0.9500 . ?
C26 C31 1.376(18) . ?
C26 C27 1.406(12) . ?
C27 C28 1.360(18) . ?
C27 H26 0.9500 . ?
C28 C29 1.414(18) . ?
C28 H27 0.9500 . ?
C29 O2 1.356(16) . ?
C29 C30 1.386(13) . ?
C30 C31 1.394(18) . ?
C30 H28 0.9500 . ?
C31 H29 0.9500 . ?
C32 O2 1.468(15) . ?
C32 C33 1.519(16) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.505(13) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.519(16) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.529(14) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?

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
C2 C1 N1 116.1(10) . . ?
C2 C1 C6 119.0(13) . . ?
N1 C1 C6 124.9(10) . . ?
C3 C2 C1 120.4(10) . . ?
C3 C2 H1 119.8 . . ?
C1 C2 H1 119.8 . . ?
C2 C3 C4 119.1(10) . . ?
C2 C3 H2 120.4 . . ?
C4 C3 H2 120.4 . . ?
C5 C4 C3 121.7(13) . . ?
C5 C4 Cl1 119.3(9) . . ?
C3 C4 Cl1 118.8(9) . . ?
C6 C5 C4 118.9(10) . . ?
C6 C5 H3 120.5 . . ?
C4 C5 H3 120.5 . . ?
C5 C6 C1 120.5(10) . . ?
C5 C6 H4 119.7 . . ?
C1 C6 H4 119.7 . . ?
N1 C7 C8 121.0(12) . . ?
N1 C7 H5 119.5 . . ?
C8 C7 H5 119.5 . . ?
C13 C8 C9 119.8(14) . . ?
C13 C8 C7 120.7(11) . . ?
C9 C8 C7 119.4(13) . . ?
C8 C9 C10 118.7(13) . . ?
C8 C9 H6 120.7 . . ?
C10 C9 H6 120.7 . . ?
C11 C10 C9 120.7(11) . . ?
C11 C10 H7 119.7 . . ?
C9 C10 H7 119.7 . . ?
O1 C11 C10 117.2(11) . . ?
O1 C11 C12 123.2(13) . . ?
C10 C11 C12 119.7(14) . . ?
C13 C12 C11 118.0(13) . . ?
C13 C12 H8 121.0 . . ?
C11 C12 H8 121.0 . . ?
C8 C13 C12 123.1(11) . . ?
C8 C13 H9 118.5 . . ?
C12 C13 H9 118.5 . . ?
O1 C14 C15 108.2(9) . . ?
O1 C14 H14A 110.1 . . ?
C15 C14 H14A 110.1 . . ?
O1 C14 H14B 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
C14 C15 C16 114.8(11) . . ?
C14 C15 H15A 108.6 . . ?
C16 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
C16 C15 H15B 108.6 . . ?
H15A C15 H15B 107.5 . . ?
C17 C16 C15 113.7(11) . . ?
C17 C16 H16A 108.8 . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 C18 112.6(11) . . ?
C16 C17 H17A 109.1 . . ?
C18 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 N1 C1 121.6(11) . . ?
C11 O1 C14 117.1(9) . . ?
N2 C19 C20 116.5(10) . . ?
N2 C19 C24 125.8(9) . . ?
C20 C19 C24 117.7(13) . . ?
C21 C20 C19 120.9(11) . . ?
C21 C20 H21 119.6 . . ?
C19 C20 H21 119.6 . . ?
C20 C21 C22 119.8(10) . . ?
C20 C21 H22 120.1 . . ?
C22 C21 H22 120.1 . . ?
C21 C22 C23 120.4(13) . . ?
C21 C22 Cl2 119.2(9) . . ?
C23 C22 Cl2 120.4(9) . . ?
C24 C23 C22 119.8(11) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C19 121.2(10) . . ?
C23 C24 H24 119.4 . . ?
C19 C24 H24 119.4 . . ?
N2 C25 C26 120.7(12) . . ?
N2 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C31 C26 C27 119.3(13) . . ?
C31 C26 C25 120.8(10) . . ?
C27 C26 C25 119.9(12) . . ?
C28 C27 C26 119.4(13) . . ?
C28 C27 H26 120.3 . . ?
C26 C27 H26 120.3 . . ?
C27 C28 C29 121.6(11) . . ?
C27 C28 H27 119.2 . . ?
C29 C28 H27 119.2 . . ?
O2 C29 C30 124.4(13) . . ?
O2 C29 C28 116.7(10) . . ?
C30 C29 C28 118.8(14) . . ?
C29 C30 C31 119.2(13) . . ?
C29 C30 H28 120.4 . . ?
C31 C30 H28 120.4 . . ?
C26 C31 C30 121.6(10) . . ?
C26 C31 H29 119.2 . . ?
C30 C31 H29 119.2 . . ?
O2 C32 C33 106.9(8) . . ?
O2 C32 H32A 110.3 . . ?
C33 C32 H32A 110.3 . . ?
O2 C32 H32B 110.3 . . ?
C33 C32 H32B 110.3 . . ?
H32A C32 H32B 108.6 . . ?
C34 C33 C32 114.5(12) . . ?
C34 C33 H33A 108.6 . . ?
C32 C33 H33A 108.6 . . ?
C34 C33 H33B 108.6 . . ?
C32 C33 H33B 108.6 . . ?
H33A C33 H33B 107.6 . . ?
C33 C34 C35 114.4(12) . . ?
C33 C34 H34A 108.7 . . ?
C35 C34 H34A 108.7 . . ?
C33 C34 H34B 108.7 . . ?
C35 C34 H34B 108.7 . . ?
H34A C34 H34B 107.6 . . ?
C34 C35 C36 115.4(9) . . ?
C34 C35 H35A 108.4 . . ?
C36 C35 H35A 108.4 . . ?
C34 C35 H35B 108.4 . . ?
C36 C35 H35B 108.4 . . ?
H35A C35 H35B 107.5 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C25 N2 C19 121.4(11) . . ?
C29 O2 C32 117.6(8) . . ?

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 C2 C3 179.9(11) . . . . ?
C6 C1 C2 C3 2.2(18) . . . . ?
C1 C2 C3 C4 -0.6(18) . . . . ?
C2 C3 C4 C5 -3.8(18) . . . . ?
C2 C3 C4 Cl1 -179.7(9) . . . . ?
C3 C4 C5 C6 6.3(18) . . . . ?
Cl1 C4 C5 C6 -177.8(9) . . . . ?
C4 C5 C6 C1 -4.6(18) . . . . ?
C2 C1 C6 C5 0.4(18) . . . . ?
N1 C1 C6 C5 -177.0(11) . . . . ?
N1 C7 C8 C13 -6.2(15) . . . . ?
N1 C7 C8 C9 172.4(9) . . . . ?
C13 C8 C9 C10 0.0(15) . . . . ?
C7 C8 C9 C10 -178.5(9) . . . . ?
C8 C9 C10 C11 -0.4(16) . . . . ?
C9 C10 C11 O1 178.9(9) . . . . ?
C9 C10 C11 C12 -0.5(16) . . . . ?
O1 C11 C12 C13 -177.6(10) . . . . ?
C10 C11 C12 C13 1.7(15) . . . . ?
C9 C8 C13 C12 1.3(16) . . . . ?
C7 C8 C13 C12 179.9(9) . . . . ?
C11 C12 C13 C8 -2.2(16) . . . . ?
O1 C14 C15 C16 -67.9(10) . . . . ?
C14 C15 C16 C17 -173.6(9) . . . . ?
C15 C16 C17 C18 177.5(8) . . . . ?
C8 C7 N1 C1 179.3(9) . . . . ?
C2 C1 N1 C7 146.5(10) . . . . ?
C6 C1 N1 C7 -36.0(17) . . . . ?
C10 C11 O1 C14 175.1(9) . . . . ?
C12 C11 O1 C14 -5.6(14) . . . . ?
C15 C14 O1 C11 179.1(8) . . . . ?
N2 C19 C20 C21 179.3(11) . . . . ?
C24 C19 C20 C21 -2.8(17) . . . . ?
C19 C20 C21 C22 1.0(18) . . . . ?
C20 C21 C22 C23 2.5(18) . . . . ?
C20 C21 C22 Cl2 179.8(9) . . . . ?
C21 C22 C23 C24 -4.2(18) . . . . ?
Cl2 C22 C23 C24 178.6(10) . . . . ?
C22 C23 C24 C19 2.3(19) . . . . ?
N2 C19 C24 C23 178.9(11) . . . . ?
C20 C19 C24 C23 1.2(18) . . . . ?
N2 C25 C26 C31 2.5(15) . . . . ?
N2 C25 C26 C27 -177.9(9) . . . . ?
C31 C26 C27 C28 -1.1(15) . . . . ?
C25 C26 C27 C28 179.3(9) . . . . ?
C26 C27 C28 C29 0.7(16) . . . . ?
C27 C28 C29 O2 -178.2(9) . . . . ?
C27 C28 C29 C30 -0.4(15) . . . . ?
O2 C29 C30 C31 178.1(9) . . . . ?
C28 C29 C30 C31 0.5(14) . . . . ?
C27 C26 C31 C30 1.2(15) . . . . ?
C25 C26 C31 C30 -179.2(9) . . . . ?
C29 C30 C31 C26 -0.9(15) . . . . ?
O2 C32 C33 C34 67.2(10) . . . . ?
C32 C33 C34 C35 167.8(9) . . . . ?
C33 C34 C35 C36 62.1(14) . . . . ?
C26 C25 N2 C19 -177.4(9) . . . . ?
C20 C19 N2 C25 -147.5(10) . . . . ?
C24 C19 N2 C25 34.8(17) . . . . ?
C30 C29 O2 C32 2.6(14) . . . . ?
C28 C29 O2 C32 -179.7(8) . . . . ?
C33 C32 O2 C29 -171.6(8) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


