# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_1
_database_code_depnum_ccdc_archive 'CCDC 1515391'
_audit_update_record             
;
2016-11-07 deposited with the CCDC.
2017-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H19 N O'
_chemical_formula_weight         205.29

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.555(6)
_cell_length_b                   6.165(2)
_cell_length_c                   10.117(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.628(6)
_cell_angle_gamma                90.00
_cell_volume                     1206.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.131
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9860
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5780
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_sigmaI/netI    0.0743
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2113
_reflns_number_gt                1556
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0434P)²+0.6500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2113
_refine_ls_number_parameters     141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.1618
_refine_ls_wR_factor_gt          0.1477
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.44947(9) 0.7828(3) -0.08822(15) 0.0624(6) Uani 1 1 d . . .
N1 N 0.46249(10) 0.8440(3) 0.13127(17) 0.0544(6) Uani 1 1 d . . .
H1A H 0.4922 0.9452 0.1258 0.065 Uiso 1 1 calc R . .
H1B H 0.4511 0.8108 0.2076 0.065 Uiso 1 1 calc R . .
C1 C 0.12653(12) 0.9225(4) 0.1918(2) 0.0519(6) Uani 1 1 d . . .
C2 C 0.09453(15) 1.0975(5) 0.0957(3) 0.0793(9) Uani 1 1 d . . .
H2A H 0.0855 1.0392 0.0068 0.119 Uiso 1 1 calc R . .
H2B H 0.1260 1.2174 0.0974 0.119 Uiso 1 1 calc R . .
H2C H 0.0520 1.1463 0.1222 0.119 Uiso 1 1 calc R . .
C3 C 0.14354(18) 1.0245(6) 0.3288(3) 0.0954(12) Uani 1 1 d . . .
H3A H 0.1021 1.0823 0.3555 0.143 Uiso 1 1 calc R . .
H3B H 0.1765 1.1392 0.3258 0.143 Uiso 1 1 calc R . .
H3C H 0.1628 0.9166 0.3921 0.143 Uiso 1 1 calc R . .
C4 C 0.07308(16) 0.7470(6) 0.1925(4) 0.1066(13) Uani 1 1 d . . .
H4A H 0.0895 0.6411 0.2593 0.160 Uiso 1 1 calc R . .
H4B H 0.0649 0.6785 0.1063 0.160 Uiso 1 1 calc R . .
H4C H 0.0308 0.8094 0.2121 0.160 Uiso 1 1 calc R . .
C5 C 0.19331(11) 0.8319(3) 0.15133(19) 0.0416(5) Uani 1 1 d . . .
C6 C 0.23140(12) 0.9429(4) 0.0698(2) 0.0504(6) Uani 1 1 d . . .
H6 H 0.2159 1.0776 0.0364 0.060 Uiso 1 1 calc R . .
C7 C 0.29207(12) 0.8603(4) 0.0360(2) 0.0491(6) Uani 1 1 d . . .
H7 H 0.3162 0.9399 -0.0199 0.059 Uiso 1 1 calc R . .
C8 C 0.31756(10) 0.6620(3) 0.08353(19) 0.0390(5) Uani 1 1 d . . .
C9 C 0.28026(12) 0.5509(4) 0.1655(2) 0.0492(6) Uani 1 1 d . . .
H9 H 0.2962 0.4170 0.1994 0.059 Uiso 1 1 calc R . .
C10 C 0.21941(12) 0.6332(4) 0.1989(2) 0.0498(6) Uani 1 1 d . . .
H10 H 0.1954 0.5531 0.2548 0.060 Uiso 1 1 calc R . .
C11 C 0.38207(11) 0.5647(4) 0.0406(2) 0.0469(6) Uani 1 1 d . . .
H11 H 0.4032 0.4677 0.1120 0.056 Uiso 1 1 calc R . .
C12 C 0.43425(11) 0.7391(4) 0.0219(2) 0.0446(5) Uani 1 1 d . . .
C13 C 0.36351(14) 0.4301(4) -0.0860(3) 0.0639(7) Uani 1 1 d . . .
H13A H 0.3427 0.5219 -0.1575 0.096 Uiso 1 1 calc R . .
H13B H 0.3315 0.3182 -0.0705 0.096 Uiso 1 1 calc R . .
H13C H 0.4046 0.3655 -0.1097 0.096 Uiso 1 1 calc R . .


_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 C12 1.225(2) . ?
N1 C12 1.328(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C1 C4 1.505(4) . ?
C1 C3 1.513(4) . ?
C1 C2 1.523(4) . ?
C1 C5 1.532(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.374(3) . ?
C5 C10 1.385(3) . ?
C6 C7 1.381(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.379(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.367(3) . ?
C8 C11 1.518(3) . ?
C9 C10 1.381(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.514(3) . ?
C11 C13 1.524(3) . ?
C11 H11 0.9800 . ?
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
C12 N1 H1A 120.0 . . ?
C12 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C4 C1 C3 110.6(3) . . ?
C4 C1 C2 107.0(2) . . ?
C3 C1 C2 107.7(2) . . ?
C4 C1 C5 111.1(2) . . ?
C3 C1 C5 108.5(2) . . ?
C2 C1 C5 111.88(19) . . ?
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 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 116.4(2) . . ?
C6 C5 C1 122.6(2) . . ?
C10 C5 C1 120.94(19) . . ?
C5 C6 C7 121.9(2) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C6 121.3(2) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C9 C8 C7 117.2(2) . . ?
C9 C8 C11 121.14(19) . . ?
C7 C8 C11 121.55(18) . . ?
C8 C9 C10 121.5(2) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C5 121.7(2) . . ?
C9 C10 H10 119.1 . . ?
C5 C10 H10 119.1 . . ?
C12 C11 C8 111.08(18) . . ?
C12 C11 C13 111.20(18) . . ?
C8 C11 C13 110.62(18) . . ?
C12 C11 H11 107.9 . . ?
C8 C11 H11 107.9 . . ?
C13 C11 H11 107.9 . . ?
O1 C12 N1 121.5(2) . . ?
O1 C12 C11 122.01(19) . . ?
N1 C12 C11 116.45(18) . . ?
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 . . ?

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
C4 C1 C5 C6 140.5(3) . . . . ?
C3 C1 C5 C6 -97.7(3) . . . . ?
C2 C1 C5 C6 20.9(3) . . . . ?
C4 C1 C5 C10 -41.2(3) . . . . ?
C3 C1 C5 C10 80.6(3) . . . . ?
C2 C1 C5 C10 -160.8(2) . . . . ?
C10 C5 C6 C7 0.6(3) . . . . ?
C1 C5 C6 C7 179.0(2) . . . . ?
C5 C6 C7 C8 -0.4(4) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C6 C7 C8 C11 176.6(2) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C11 C8 C9 C10 -176.3(2) . . . . ?
C8 C9 C10 C5 -0.1(4) . . . . ?
C6 C5 C10 C9 -0.3(3) . . . . ?
C1 C5 C10 C9 -178.8(2) . . . . ?
C9 C8 C11 C12 -147.9(2) . . . . ?
C7 C8 C11 C12 35.6(3) . . . . ?
C9 C8 C11 C13 88.1(3) . . . . ?
C7 C8 C11 C13 -88.4(3) . . . . ?
C8 C11 C12 O1 -112.9(2) . . . . ?
C13 C11 C12 O1 10.7(3) . . . . ?
C8 C11 C12 N1 66.6(3) . . . . ?
C13 C11 C12 N1 -169.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1515399'
_audit_update_record             
;
2016-11-07 deposited with the CCDC.
2017-10-24 downloaded from the CCDC.
;
_audit_creation_date             2016-01-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C9 H10 Cl N O'
_chemical_formula_sum            'C9 H10 Cl N O'
_chemical_formula_weight         183.63
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   27.159(13)
_cell_length_b                   7.490(4)
_cell_length_c                   9.539(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.510(8)
_cell_angle_gamma                90
_cell_volume                     1860.4(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1412
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.35
_cell_measurement_theta_min      3.13
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.899
_exptl_absorpt_coefficient_mu    0.361
_exptl_absorpt_correction_T_max  0.9313
_exptl_absorpt_correction_T_min  0.8994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4853
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         1.564
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1215
_reflns_number_total             1833
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1833
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0735
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1764P)²+0.3762P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2312
_refine_ls_wR_factor_ref         0.2723
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2. Others
 Fixed Sof: C1(0.5) H1(0.5) C3(0.5) H3(0.5) C4(0.5) H4(0.5) C6(0.5) H6(0.5)
 C1'(0.5) H1'(0.5) C3'(0.5) H3'(0.5) C4'(0.5) H4'(0.5) C6'(0.5) H6'(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C6AA(H6AA,H6AB), C8(H8A,H8B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C6(H6), C1'(H1'), C3'(H3'), C4'(H4'), C6'(H6')
3.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Cl1 Cl 0.03584(6) 0.14735(19) 0.61094(18) 0.1276(7) Uani 1 1 d . . . . .
O1 O 0.21826(9) 1.0520(3) 1.05085(19) 0.0622(7) Uani 1 1 d . . . . .
N1 N 0.23130(11) 1.1061(4) 0.8360(3) 0.0636(8) Uani 1 1 d . . . . .
H1A H 0.2484 1.2016 0.8683 0.076 Uiso 1 1 calc R . . . .
H1B H 0.2267 1.0739 0.7467 0.076 Uiso 1 1 calc R . . . .
C2 C 0.11716(13) 0.6219(4) 0.8518(4) 0.0613(9) Uani 1 1 d . . . . .
C5 C 0.06707(16) 0.3290(5) 0.7069(5) 0.0752(11) Uani 1 1 d . . . . .
C6AA C 0.14578(14) 0.7822(5) 0.9289(4) 0.0738(11) Uani 1 1 d . . . . .
H6AA H 0.1216 0.8779 0.9279 0.089 Uiso 1 1 calc R . . . .
H6AB H 0.1626 0.7519 1.0301 0.089 Uiso 1 1 calc R . . . .
C8 C 0.18452(15) 0.8445(4) 0.8590(4) 0.0694(10) Uani 1 1 d . . . . .
H8A H 0.1677 0.8652 0.7562 0.083 Uiso 1 1 calc R . . . .
H8B H 0.2095 0.7499 0.8655 0.083 Uiso 1 1 calc R . . . .
C9 C 0.21246(11) 1.0104(4) 0.9226(3) 0.0507(7) Uani 1 1 d . . . . .
C1 C 0.1232(3) 0.4691(10) 0.9262(9) 0.0636(17) Uani 0.5 1 d . . P A 1
H1 H 0.1431 0.4654 1.0233 0.076 Uiso 0.5 1 calc R . P A 1
C3 C 0.0897(3) 0.6333(10) 0.7126(9) 0.0704(19) Uani 0.5 1 d . . P A 1
H3 H 0.0859 0.7426 0.6643 0.084 Uiso 0.5 1 calc R . P A 1
C4 C 0.0671(3) 0.4832(13) 0.6406(9) 0.080(2) Uani 0.5 1 d . . P A 1
H4 H 0.0510 0.4904 0.5407 0.096 Uiso 0.5 1 calc R . P A 1
C6 C 0.0998(3) 0.3166(12) 0.8579(10) 0.074(2) Uani 0.5 1 d . . P A 1
H6 H 0.1047 0.2077 0.9068 0.089 Uiso 0.5 1 calc R . P A 1
C1' C 0.1378(3) 0.4523(11) 0.8553(10) 0.071(2) Uani 0.5 1 d . . P A 2
H1' H 0.1718 0.4335 0.9094 0.086 Uiso 0.5 1 calc R . P A 2
C3' C 0.0655(3) 0.6350(9) 0.7661(7) 0.0644(17) Uani 0.5 1 d . . P A 2
H3' H 0.0488 0.7446 0.7598 0.077 Uiso 0.5 1 calc R . P A 2
C4' C 0.0395(3) 0.4945(10) 0.6933(8) 0.0662(17) Uani 0.5 1 d . . P A 2
H4' H 0.0055 0.5041 0.6371 0.079 Uiso 0.5 1 calc R . P A 2
C6' C 0.1095(4) 0.3084(12) 0.7806(11) 0.077(2) Uani 0.5 1 d . . P A 2
H6' H 0.1242 0.1954 0.7891 0.092 Uiso 0.5 1 calc R . P A 2


_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
Cl1 C5 1.723(4) . ?
O1 C9 1.229(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C9 1.303(4) . ?
C2 C6AA 1.504(4) . ?
C2 C1 1.332(8) . ?
C2 C3 1.328(8) . ?
C2 C1' 1.386(10) . ?
C2 C3' 1.414(9) . ?
C5 C4 1.316(10) . ?
C5 C6 1.466(10) . ?
C5 C4' 1.435(9) . ?
C5 C6' 1.176(10) . ?
C6AA H6AA 0.9700 . ?
C6AA H6AB 0.9700 . ?
C6AA C8 1.472(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.492(4) . ?
C1 H1 0.9300 . ?
C1 C6 1.378(11) . ?
C3 H3 0.9300 . ?
C3 C4 1.369(11) . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?
C1' H1' 0.9300 . ?
C1' C6' 1.397(12) . ?
C3' H3' 0.9300 . ?
C3' C4' 1.345(9) . ?
C4' H4' 0.9300 . ?
C6' H6' 0.9300 . ?

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
H1A N1 H1B 120.0 . . ?
C9 N1 H1A 120.0 . . ?
C9 N1 H1B 120.0 . . ?
C1 C2 C6AA 117.2(4) . . ?
C3 C2 C6AA 120.2(4) . . ?
C3 C2 C1 122.5(5) . . ?
C1' C2 C6AA 124.8(4) . . ?
C1' C2 C3' 114.0(5) . . ?
C3' C2 C6AA 121.2(4) . . ?
C4 C5 Cl1 120.3(4) . . ?
C4 C5 C6 116.4(5) . . ?
C6 C5 Cl1 122.8(4) . . ?
C4' C5 Cl1 118.0(4) . . ?
C6' C5 Cl1 117.7(5) . . ?
C6' C5 C4' 124.4(6) . . ?
C2 C6AA H6AA 109.3 . . ?
C2 C6AA H6AB 109.3 . . ?
H6AA C6AA H6AB 108.0 . . ?
C8 C6AA C2 111.6(3) . . ?
C8 C6AA H6AA 109.3 . . ?
C8 C6AA H6AB 109.3 . . ?
C6AA C8 H8A 108.5 . . ?
C6AA C8 H8B 108.5 . . ?
C6AA C8 C9 115.2(3) . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
O1 C9 N1 121.9(3) . . ?
O1 C9 C8 121.5(3) . . ?
N1 C9 C8 116.6(2) . . ?
C2 C1 H1 120.3 . . ?
C2 C1 C6 119.3(7) . . ?
C6 C1 H1 120.3 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.5(7) . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 122.8(7) . . ?
C5 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
C5 C6 H6 120.6 . . ?
C1 C6 C5 118.8(7) . . ?
C1 C6 H6 120.6 . . ?
C2 C1' H1' 118.9 . . ?
C2 C1' C6' 122.3(7) . . ?
C6' C1' H1' 118.9 . . ?
C2 C3' H3' 118.9 . . ?
C4' C3' C2 122.2(6) . . ?
C4' C3' H3' 118.9 . . ?
C5 C4' H4' 121.8 . . ?
C3' C4' C5 116.5(6) . . ?
C3' C4' H4' 121.8 . . ?
C5 C6' C1' 120.6(8) . . ?
C5 C6' H6' 119.7 . . ?
C1' C6' H6' 119.7 . . ?

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
Cl1 C5 C4 C3 177.6(7) . . . . ?
Cl1 C5 C6 C1 -179.9(6) . . . . ?
Cl1 C5 C4' C3' -178.1(5) . . . . ?
Cl1 C5 C6' C1' 176.8(7) . . . . ?
C2 C6AA C8 C9 176.2(3) . . . . ?
C2 C1 C6 C5 -2.6(12) . . . . ?
C2 C3 C4 C5 6.7(14) . . . . ?
C2 C1' C6' C5 2.9(14) . . . . ?
C2 C3' C4' C5 -0.1(11) . . . . ?
C6AA C2 C1 C6 -176.8(6) . . . . ?
C6AA C2 C3 C4 175.0(7) . . . . ?
C6AA C2 C1' C6' -179.5(7) . . . . ?
C6AA C2 C3' C4' 178.3(6) . . . . ?
C6AA C8 C9 O1 27.0(5) . . . . ?
C6AA C8 C9 N1 -154.5(3) . . . . ?
C1 C2 C6AA C8 114.9(6) . . . . ?
C1 C2 C3 C4 -0.9(12) . . . . ?
C3 C2 C6AA C8 -61.2(7) . . . . ?
C3 C2 C1 C6 -0.8(12) . . . . ?
C4 C5 C6 C1 7.7(11) . . . . ?
C6 C5 C4 C3 -9.8(12) . . . . ?
C1' C2 C6AA C8 71.2(7) . . . . ?
C1' C2 C3' C4' -1.0(10) . . . . ?
C3' C2 C6AA C8 -108.0(5) . . . . ?
C3' C2 C1' C6' -0.2(11) . . . . ?
C4' C5 C6' C1' -4.2(14) . . . . ?
C6' C5 C4' C3' 2.9(12) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1552470'
_audit_update_record             
;
2017-05-26 deposited with the CCDC.
2017-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H36 Cl O P Pd'
_chemical_formula_weight         477.32

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.6745(3)
_cell_length_b                   9.6624(4)
_cell_length_c                   13.8499(5)
_cell_angle_alpha                86.795(3)
_cell_angle_beta                 81.245(3)
_cell_angle_gamma                81.324(3)
_cell_volume                     1133.55(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    6386
_cell_measurement_theta_min      4.2690
_cell_measurement_theta_max      29.2010

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    1.014
_shelx_estimated_absorpt_T_min   0.786
_shelx_estimated_absorpt_T_max   0.815
_exptl_absorpt_correction_T_min  0.88509
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_reflns_number            11150
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.435
_diffrn_reflns_theta_max         29.575
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.842
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.842
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5355
_reflns_number_gt                4810
_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       'CrysAlisPro (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_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)+(0.0259P)²+0.0350P] 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_number_reflns         5355
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0658
_refine_ls_wR_factor_gt          0.0627
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
Pd1 Pd 0.39264(2) 0.56625(2) 0.35391(2) 0.02864(6) Uani 1 1 d . . . . .
P1 P 0.43107(5) 0.75255(5) 0.24671(3) 0.02526(11) Uani 1 1 d . . . . .
Cl1 Cl 0.41490(6) 0.34132(6) 0.42658(4) 0.04429(14) Uani 1 1 d . . . . .
O1 O 0.06552(17) 0.6355(2) 0.37131(11) 0.0514(5) Uani 1 1 d . . . . .
C1 C 0.1759(2) 0.6223(2) 0.41330(15) 0.0325(5) Uani 1 1 d . . . . .
C2 C 0.1689(2) 0.6305(2) 0.52297(14) 0.0339(5) Uani 1 1 d . . . . .
H2A H 0.2668 0.6569 0.5366 0.041 Uiso 1 1 calc R U . . .
H2B H 0.1590 0.5387 0.5532 0.041 Uiso 1 1 calc R U . . .
C10 C 0.4452(2) 0.9236(2) 0.30360(15) 0.0347(5) Uani 1 1 d . . . . .
C14 C 0.6332(2) 0.6771(2) 0.18129(16) 0.0385(5) Uani 1 1 d . . . . .
C5 C -0.0920(2) 0.6937(2) 0.74199(16) 0.0377(5) Uani 1 1 d . . . . .
H5 H -0.1725 0.6585 0.7183 0.045 Uiso 1 1 calc R U . . .
C4 C 0.0279(2) 0.7414(2) 0.67704(15) 0.0329(4) Uani 1 1 d . . . . .
C6 C -0.0932(3) 0.6978(3) 0.84184(16) 0.0452(6) Uani 1 1 d . . . . .
H6 H -0.1747 0.6657 0.8846 0.054 Uiso 1 1 calc R U . . .
C18 C 0.2861(2) 0.7875(2) 0.15450(15) 0.0373(5) Uani 1 1 d . . . . .
C11 C 0.3012(3) 0.9549(3) 0.38361(18) 0.0519(6) Uani 1 1 d . . . . .
H11A H 0.2062 0.9554 0.3558 0.078 Uiso 1 1 calc R U . . .
H11B H 0.3011 1.0448 0.4099 0.078 Uiso 1 1 calc R U . . .
H11C H 0.3067 0.8840 0.4349 0.078 Uiso 1 1 calc R U . . .
C3 C 0.0317(2) 0.7357(3) 0.56801(15) 0.0394(5) Uani 1 1 d . . . . .
H3A H 0.0415 0.8278 0.5382 0.047 Uiso 1 1 calc R U . . .
H3B H -0.0665 0.7096 0.5547 0.047 Uiso 1 1 calc R U . . .
C12 C 0.5899(3) 0.9073(3) 0.35790(17) 0.0484(6) Uani 1 1 d . . . . .
H12A H 0.5883 0.8269 0.4018 0.073 Uiso 1 1 calc R U . . .
H12B H 0.5868 0.9896 0.3943 0.073 Uiso 1 1 calc R U . . .
H12C H 0.6845 0.8952 0.3113 0.073 Uiso 1 1 calc R U . . .
C13 C 0.4535(3) 1.0492(2) 0.23175(18) 0.0460(6) Uani 1 1 d . . . . .
H13A H 0.5405 1.0280 0.1805 0.069 Uiso 1 1 calc R U . . .
H13B H 0.4681 1.1293 0.2655 0.069 Uiso 1 1 calc R U . . .
H13C H 0.3573 1.0691 0.2041 0.069 Uiso 1 1 calc R U . . .
C7 C 0.0251(3) 0.7491(3) 0.87825(17) 0.0484(6) Uani 1 1 d . . . . .
H7 H 0.0233 0.7530 0.9454 0.058 Uiso 1 1 calc R U . . .
C21 C 0.1358(3) 0.8817(3) 0.1977(2) 0.0540(7) Uani 1 1 d . . . . .
H21A H 0.0915 0.8402 0.2582 0.081 Uiso 1 1 calc R U . . .
H21B H 0.0607 0.8916 0.1525 0.081 Uiso 1 1 calc R U . . .
H21C H 0.1609 0.9722 0.2092 0.081 Uiso 1 1 calc R U . . .
C17 C 0.7286(3) 0.6038(3) 0.26034(19) 0.0536(7) Uani 1 1 d . . . . .
H17A H 0.7423 0.6717 0.3051 0.080 Uiso 1 1 calc R U . . .
H17B H 0.8298 0.5607 0.2297 0.080 Uiso 1 1 calc R U . . .
H17C H 0.6726 0.5335 0.2952 0.080 Uiso 1 1 calc R U . . .
C19 C 0.2350(3) 0.6463(3) 0.13465(18) 0.0498(6) Uani 1 1 d . . . . .
H19A H 0.3252 0.5843 0.1058 0.075 Uiso 1 1 calc R U . . .
H19B H 0.1580 0.6621 0.0908 0.075 Uiso 1 1 calc R U . . .
H19C H 0.1902 0.6050 0.1951 0.075 Uiso 1 1 calc R U . . .
C15 C 0.6193(3) 0.5619(3) 0.11397(19) 0.0601(7) Uani 1 1 d . . . . .
H15A H 0.5582 0.4957 0.1496 0.090 Uiso 1 1 calc R U . . .
H15B H 0.7225 0.5152 0.0898 0.090 Uiso 1 1 calc R U . . .
H15C H 0.5683 0.6022 0.0600 0.090 Uiso 1 1 calc R U . . .
C8 C 0.1455(3) 0.7942(3) 0.81454(18) 0.0517(6) Uani 1 1 d . . . . .
H8 H 0.2276 0.8264 0.8385 0.062 Uiso 1 1 calc R U . . .
C9 C 0.1459(3) 0.7923(3) 0.71547(17) 0.0456(6) Uani 1 1 d . . . . .
H9 H 0.2271 0.8259 0.6733 0.055 Uiso 1 1 calc R U . . .
C20 C 0.3525(3) 0.8553(3) 0.05659(18) 0.0580(7) Uani 1 1 d . . . . .
H20A H 0.3889 0.9409 0.0687 0.087 Uiso 1 1 calc R U . . .
H20B H 0.2713 0.8750 0.0157 0.087 Uiso 1 1 calc R U . . .
H20C H 0.4388 0.7922 0.0244 0.087 Uiso 1 1 calc R U . . .
C16 C 0.7289(3) 0.7835(3) 0.12157(19) 0.0576(7) Uani 1 1 d . . . . .
H16A H 0.6712 0.8283 0.0717 0.086 Uiso 1 1 calc R U . . .
H16B H 0.8283 0.7355 0.0918 0.086 Uiso 1 1 calc R U . . .
H16C H 0.7466 0.8527 0.1641 0.086 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
Pd1 C1 1.944(2) . ?
Pd1 P1 2.2995(5) . ?
Pd1 Cl1 2.3371(6) . ?
P1 C10 1.898(2) . ?
P1 C14 1.905(2) . ?
P1 C18 1.9078(19) . ?
O1 C1 1.181(2) . ?
C1 C2 1.517(3) . ?
C2 C3 1.523(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C10 C13 1.529(3) . ?
C10 C12 1.542(3) . ?
C10 C11 1.543(3) . ?
C14 C15 1.521(3) . ?
C14 C16 1.543(3) . ?
C14 C17 1.548(3) . ?
C5 C6 1.384(3) . ?
C5 C4 1.385(3) . ?
C5 H5 0.9300 . ?
C4 C9 1.386(3) . ?
C4 C3 1.509(3) . ?
C6 C7 1.375(3) . ?
C6 H6 0.9300 . ?
C18 C21 1.533(3) . ?
C18 C20 1.542(3) . ?
C18 C19 1.547(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C7 C8 1.369(3) . ?
C7 H7 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C8 C9 1.373(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C1 Pd1 P1 100.99(6) . . ?
C1 Pd1 Cl1 95.22(6) . . ?
P1 Pd1 Cl1 161.97(2) . . ?
C10 P1 C14 109.41(10) . . ?
C10 P1 C18 109.15(10) . . ?
C14 P1 C18 109.26(10) . . ?
C10 P1 Pd1 116.04(6) . . ?
C14 P1 Pd1 97.67(7) . . ?
C18 P1 Pd1 114.55(7) . . ?
O1 C1 C2 125.31(18) . . ?
O1 C1 Pd1 124.83(16) . . ?
C2 C1 Pd1 109.54(13) . . ?
C1 C2 C3 112.53(17) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C13 C10 C12 108.37(17) . . ?
C13 C10 C11 109.59(19) . . ?
C12 C10 C11 105.18(19) . . ?
C13 C10 P1 114.90(15) . . ?
C12 C10 P1 110.44(16) . . ?
C11 C10 P1 107.91(14) . . ?
C15 C14 C16 108.2(2) . . ?
C15 C14 C17 105.4(2) . . ?
C16 C14 C17 108.99(18) . . ?
C15 C14 P1 110.72(15) . . ?
C16 C14 P1 115.87(17) . . ?
C17 C14 P1 107.07(15) . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C4 C9 117.78(19) . . ?
C5 C4 C3 121.16(18) . . ?
C9 C4 C3 121.05(18) . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C21 C18 C20 108.3(2) . . ?
C21 C18 C19 106.32(18) . . ?
C20 C18 C19 109.1(2) . . ?
C21 C18 P1 110.62(16) . . ?
C20 C18 P1 114.23(14) . . ?
C19 C18 P1 108.05(15) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C3 C2 111.25(17) . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C7 C6 119.2(2) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 C8 C9 120.5(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C4 121.4(2) . . ?
C8 C9 H9 119.3 . . ?
C4 C9 H9 119.3 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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 C1 C2 C3 -34.2(3) . . . . ?
Pd1 C1 C2 C3 152.00(15) . . . . ?
C14 P1 C10 C13 76.82(17) . . . . ?
C18 P1 C10 C13 -42.69(18) . . . . ?
Pd1 P1 C10 C13 -173.93(13) . . . . ?
C14 P1 C10 C12 -46.13(17) . . . . ?
C18 P1 C10 C12 -165.64(14) . . . . ?
Pd1 P1 C10 C12 63.12(15) . . . . ?
C14 P1 C10 C11 -160.59(15) . . . . ?
C18 P1 C10 C11 79.89(17) . . . . ?
Pd1 P1 C10 C11 -51.35(17) . . . . ?
C6 C5 C4 C9 0.3(3) . . . . ?
C6 C5 C4 C3 179.2(2) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C5 C4 C3 C2 -112.1(2) . . . . ?
C9 C4 C3 C2 66.8(3) . . . . ?
C1 C2 C3 C4 179.95(17) . . . . ?
C5 C6 C7 C8 -0.9(4) . . . . ?
C6 C7 C8 C9 1.9(4) . . . . ?
C7 C8 C9 C4 -1.8(4) . . . . ?
C5 C4 C9 C8 0.7(4) . . . . ?
C3 C4 C9 C8 -178.2(2) . . . . ?

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.067

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1515405'
_audit_update_record             
;
2016-11-07 deposited with the CCDC.
2017-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 N O'
_chemical_formula_weight         225.28

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.295(5)
_cell_length_b                   5.569(2)
_cell_length_c                   18.014(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.033(6)
_cell_angle_gamma                90.00
_cell_volume                     1210.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1881
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      29.71

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9772
_exptl_absorpt_correction_T_max  0.9847
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5762
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2130
_reflns_number_gt                1690
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0100P)²+0.7699P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2130
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.29005(13) 0.1084(3) 0.19213(9) 0.0372(4) Uani 1 1 d . . .
C2 C 0.35105(15) -0.1015(4) 0.20750(11) 0.0447(5) Uani 1 1 d . . .
H2 H 0.3495 -0.2153 0.1696 0.054 Uiso 1 1 calc R . .
C3 C 0.41450(16) -0.1437(4) 0.27893(12) 0.0514(5) Uani 1 1 d . . .
H3 H 0.4555 -0.2845 0.2882 0.062 Uiso 1 1 calc R . .
C4 C 0.41689(16) 0.0219(4) 0.33602(11) 0.0523(5) Uani 1 1 d . . .
H4 H 0.4587 -0.0072 0.3839 0.063 Uiso 1 1 calc R . .
C5 C 0.35644(17) 0.2320(4) 0.32152(11) 0.0526(5) Uani 1 1 d . . .
H5 H 0.3574 0.3444 0.3598 0.063 Uiso 1 1 calc R . .
C6 C 0.29485(15) 0.2748(4) 0.25047(10) 0.0440(5) Uani 1 1 d . . .
H6 H 0.2556 0.4179 0.2412 0.053 Uiso 1 1 calc R . .
C7 C 0.21519(14) 0.1662(4) 0.11607(10) 0.0409(4) Uani 1 1 d . . .
H7 H 0.2358 0.3267 0.1013 0.049 Uiso 1 1 calc R . .
C8 C 0.09372(14) 0.1795(3) 0.12500(9) 0.0388(4) Uani 1 1 d . . .
C9 C 0.04781(16) 0.0015(4) 0.16288(11) 0.0494(5) Uani 1 1 d . . .
H9 H 0.0908 -0.1300 0.1821 0.059 Uiso 1 1 calc R . .
C10 C -0.06141(17) 0.0155(4) 0.17279(12) 0.0563(6) Uani 1 1 d . . .
H10 H -0.0908 -0.1068 0.1981 0.068 Uiso 1 1 calc R . .
C11 C -0.12601(16) 0.2087(4) 0.14544(12) 0.0552(6) Uani 1 1 d . . .
H11 H -0.1988 0.2191 0.1526 0.066 Uiso 1 1 calc R . .
C12 C -0.08223(17) 0.3862(4) 0.10741(12) 0.0595(6) Uani 1 1 d . . .
H12 H -0.1257 0.5172 0.0884 0.071 Uiso 1 1 calc R . .
C13 C 0.02736(16) 0.3720(4) 0.09696(11) 0.0517(5) Uani 1 1 d . . .
H13 H 0.0560 0.4933 0.0709 0.062 Uiso 1 1 calc R . .
C14 C 0.22725(15) -0.0046(4) 0.05145(10) 0.0501(5) Uani 1 1 d . . .
H14A H 0.2150 -0.1679 0.0667 0.060 Uiso 1 1 calc R . .
H14B H 0.1704 0.0328 0.0078 0.060 Uiso 1 1 calc R . .
C15 C 0.34032(16) 0.0093(4) 0.02866(10) 0.0489(5) Uani 1 1 d . . .
N1 N 0.38337(14) -0.1955(4) 0.00993(10) 0.0611(5) Uani 1 1 d . . .
H1A H 0.4458 -0.1951 -0.0049 0.073 Uiso 1 1 calc R . .
H1B H 0.3488 -0.3285 0.0127 0.073 Uiso 1 1 calc R . .
O1 O 0.38698(12) 0.2051(3) 0.02561(8) 0.0635(4) Uani 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 C2 1.388(3) . ?
C1 C6 1.394(3) . ?
C1 C7 1.531(2) . ?
C2 C3 1.391(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C14 1.532(3) . ?
C7 C8 1.534(2) . ?
C7 H7 0.9800 . ?
C8 C13 1.383(3) . ?
C8 C9 1.384(3) . ?
C9 C10 1.390(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.398(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.525(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O1 1.238(3) . ?
C15 N1 1.328(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?

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 C6 117.78(17) . . ?
C2 C1 C7 124.40(16) . . ?
C6 C1 C7 117.80(17) . . ?
C1 C2 C3 120.87(18) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 120.36(19) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.41(18) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.11(19) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 121.46(19) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C1 C7 C14 114.85(16) . . ?
C1 C7 C8 110.29(13) . . ?
C14 C7 C8 110.33(14) . . ?
C1 C7 H7 107.0 . . ?
C14 C7 H7 107.0 . . ?
C8 C7 H7 107.0 . . ?
C13 C8 C9 117.88(17) . . ?
C13 C8 C7 121.16(17) . . ?
C9 C8 C7 120.94(17) . . ?
C8 C9 C10 121.23(19) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 119.33(19) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 120.5(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C8 C13 C12 120.76(19) . . ?
C8 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C7 113.50(16) . . ?
C15 C14 H14A 108.9 . . ?
C7 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C7 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
O1 C15 N1 122.31(18) . . ?
O1 C15 C14 120.7(2) . . ?
N1 C15 C14 116.93(19) . . ?
C15 N1 H1A 120.0 . . ?
C15 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?

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
C6 C1 C2 C3 0.2(3) . . . . ?
C7 C1 C2 C3 -177.97(16) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C7 C1 C6 C5 177.22(17) . . . . ?
C2 C1 C7 C14 -10.7(2) . . . . ?
C6 C1 C7 C14 171.18(16) . . . . ?
C2 C1 C7 C8 114.73(19) . . . . ?
C6 C1 C7 C8 -63.4(2) . . . . ?
C1 C7 C8 C13 130.55(18) . . . . ?
C14 C7 C8 C13 -101.5(2) . . . . ?
C1 C7 C8 C9 -48.0(2) . . . . ?
C14 C7 C8 C9 79.9(2) . . . . ?
C13 C8 C9 C10 -0.2(3) . . . . ?
C7 C8 C9 C10 178.39(18) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C9 C8 C13 C12 0.6(3) . . . . ?
C7 C8 C13 C12 -178.01(18) . . . . ?
C11 C12 C13 C8 -0.3(3) . . . . ?
C1 C7 C14 C15 -66.0(2) . . . . ?
C8 C7 C14 C15 168.63(17) . . . . ?
C7 C14 C15 O1 -40.1(3) . . . . ?
C7 C14 C15 N1 142.29(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.038
