# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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_gupm0624
_database_code_depnum_ccdc_archive 'CCDC 1021200'
_audit_update_record             
;
2014-08-26 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_date             2014-05-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H15 N O'
_chemical_formula_sum            'C14 H15 N O'
_chemical_formula_weight         213.27
_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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8602(6)
_cell_length_b                   8.4121(8)
_cell_length_c                   9.3329(7)
_cell_angle_alpha                102.282(7)
_cell_angle_beta                 108.921(7)
_cell_angle_gamma                93.927(7)
_cell_volume                     564.05(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1119
_cell_measurement_temperature    294.9(5)
_cell_measurement_theta_max      26.7620
_cell_measurement_theta_min      3.4500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3586
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.018
_diffrn_reflns_theta_min         2.960
_diffrn_ambient_temperature      294.9(5)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0467733000
_diffrn_orient_matrix_UB_12      0.0604310000
_diffrn_orient_matrix_UB_13      -0.0219507000
_diffrn_orient_matrix_UB_21      -0.0109033000
_diffrn_orient_matrix_UB_22      -0.0572080000
_diffrn_orient_matrix_UB_23      -0.0713245000
_diffrn_orient_matrix_UB_31      -0.0836610000
_diffrn_orient_matrix_UB_32      0.0262771000
_diffrn_orient_matrix_UB_33      -0.0362236000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1594
_reflns_number_total             2223
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0725
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0881P)²+0.3181P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1970
_refine_ls_wR_factor_ref         0.2175
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C1(H1A,H1B), C3(H3A,H3B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C14(H14), C11(H11), C10(H10), C13(H13), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O1 O 0.8271(3) 1.2546(3) 1.0294(2) 0.0680(7) Uani 1 1 d . . . . .
N1 N 1.0502(3) 1.1937(3) 0.9300(3) 0.0578(7) Uani 1 1 d . . . . .
C9 C 0.4884(3) 0.8286(3) 0.6604(3) 0.0453(6) Uani 1 1 d . . . . .
C7 C 0.8809(4) 1.1742(3) 0.9321(3) 0.0478(7) Uani 1 1 d . . . . .
C6 C 0.7752(4) 1.0336(3) 0.7971(3) 0.0464(7) Uani 1 1 d . . . . .
C8 C 0.6120(4) 0.9645(3) 0.7832(3) 0.0477(7) Uani 1 1 d . . . . .
H8 H 0.5701 1.0090 0.8633 0.057 Uiso 1 1 calc R . . . .
C14 C 0.4946(4) 0.7828(4) 0.5104(3) 0.0552(8) Uani 1 1 d . . . . .
H14 H 0.5817 0.8404 0.4853 0.066 Uiso 1 1 calc R . . . .
C11 C 0.2368(4) 0.6095(4) 0.5799(4) 0.0678(9) Uani 1 1 d . . . . .
H11 H 0.1502 0.5502 0.6042 0.081 Uiso 1 1 calc R . . . .
C10 C 0.3546(4) 0.7399(4) 0.6924(4) 0.0558(8) Uani 1 1 d . . . . .
H10 H 0.3447 0.7690 0.7910 0.067 Uiso 1 1 calc R . . . .
C4 C 1.0807(4) 1.0836(4) 0.7997(3) 0.0561(8) Uani 1 1 d . . . . .
H4 H 1.1578 1.0039 0.8379 0.067 Uiso 1 1 calc R . . . .
C13 C 0.3745(4) 0.6538(4) 0.3976(4) 0.0622(8) Uani 1 1 d . . . . .
H13 H 0.3808 0.6262 0.2978 0.075 Uiso 1 1 calc R . . . .
C5 C 0.8898(4) 0.9955(4) 0.6960(4) 0.0594(8) Uani 1 1 d . . . . .
H5A H 0.8454 1.0367 0.6031 0.071 Uiso 1 1 calc R . . . .
H5B H 0.8894 0.8779 0.6643 0.071 Uiso 1 1 calc R . . . .
C12 C 0.2459(4) 0.5662(4) 0.4321(4) 0.0666(9) Uani 1 1 d . . . . .
H12 H 0.1658 0.4785 0.3566 0.080 Uiso 1 1 calc R . . . .
C1 C 1.1914(4) 1.3376(4) 1.0048(4) 0.0599(8) Uani 1 1 d . . . . .
H1A H 1.2675 1.3322 1.1083 0.072 Uiso 1 1 calc R . . . .
H1B H 1.1386 1.4386 1.0130 0.072 Uiso 1 1 calc R . . . .
C3 C 1.1814(5) 1.1999(5) 0.7448(4) 0.0722(10) Uani 1 1 d . . . . .
H3A H 1.0980 1.2518 0.6738 0.087 Uiso 1 1 calc R . . . .
H3B H 1.2564 1.1435 0.6922 0.087 Uiso 1 1 calc R . . . .
C2 C 1.2991(5) 1.3269(4) 0.8949(4) 0.0725(10) Uani 1 1 d . . . . .
H2A H 1.4153 1.2918 0.9403 0.087 Uiso 1 1 calc R . . . .
H2B H 1.3206 1.4329 0.8735 0.087 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 C7 1.220(3) . ?
N1 C7 1.336(4) . ?
N1 C4 1.461(3) . ?
N1 C1 1.462(4) . ?
C9 C8 1.460(4) . ?
C9 C14 1.388(4) . ?
C9 C10 1.394(4) . ?
C7 C6 1.493(4) . ?
C6 C8 1.326(4) . ?
C6 C5 1.506(4) . ?
C8 H8 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.381(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.380(4) . ?
C11 C12 1.376(5) . ?
C10 H10 0.9300 . ?
C4 H4 0.9800 . ?
C4 C5 1.529(4) . ?
C4 C3 1.489(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.371(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C12 H12 0.9300 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.520(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.532(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?

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
C7 N1 C4 115.4(2) . . ?
C7 N1 C1 128.9(2) . . ?
C4 N1 C1 112.5(2) . . ?
C14 C9 C8 123.5(2) . . ?
C14 C9 C10 117.3(3) . . ?
C10 C9 C8 119.2(3) . . ?
O1 C7 N1 125.6(3) . . ?
O1 C7 C6 127.4(3) . . ?
N1 C7 C6 106.9(2) . . ?
C7 C6 C5 107.2(2) . . ?
C8 C6 C7 121.5(2) . . ?
C8 C6 C5 131.3(2) . . ?
C9 C8 H8 115.3 . . ?
C6 C8 C9 129.4(2) . . ?
C6 C8 H8 115.3 . . ?
C9 C14 H14 119.2 . . ?
C13 C14 C9 121.5(3) . . ?
C13 C14 H14 119.2 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C12 C11 C10 120.7(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
N1 C4 H4 110.1 . . ?
N1 C4 C5 103.5(2) . . ?
N1 C4 C3 101.8(2) . . ?
C5 C4 H4 110.1 . . ?
C3 C4 H4 110.1 . . ?
C3 C4 C5 120.5(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.8 . . ?
C6 C5 C4 104.5(2) . . ?
C6 C5 H5A 110.8 . . ?
C6 C5 H5B 110.8 . . ?
C4 C5 H5A 110.8 . . ?
C4 C5 H5B 110.8 . . ?
H5A C5 H5B 108.9 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.2(3) . . ?
C13 C12 H12 120.4 . . ?
N1 C1 H1A 111.1 . . ?
N1 C1 H1B 111.1 . . ?
N1 C1 C2 103.2(2) . . ?
H1A C1 H1B 109.1 . . ?
C2 C1 H1A 111.1 . . ?
C2 C1 H1B 111.1 . . ?
C4 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
C4 C3 C2 104.2(3) . . ?
H3A C3 H3B 108.9 . . ?
C2 C3 H3A 110.9 . . ?
C2 C3 H3B 110.9 . . ?
C1 C2 C3 105.5(3) . . ?
C1 C2 H2A 110.6 . . ?
C1 C2 H2B 110.6 . . ?
C3 C2 H2A 110.6 . . ?
C3 C2 H2B 110.6 . . ?
H2A C2 H2B 108.8 . . ?

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
O1 C7 C6 C8 -10.5(5) . . . . ?
O1 C7 C6 C5 170.2(3) . . . . ?
N1 C7 C6 C8 167.7(3) . . . . ?
N1 C7 C6 C5 -11.7(3) . . . . ?
N1 C4 C5 C6 -13.6(3) . . . . ?
N1 C4 C3 C2 35.3(3) . . . . ?
N1 C1 C2 C3 13.5(4) . . . . ?
C9 C14 C13 C12 -0.6(5) . . . . ?
C7 N1 C4 C5 7.3(4) . . . . ?
C7 N1 C4 C3 133.0(3) . . . . ?
C7 N1 C1 C2 -149.2(3) . . . . ?
C7 C6 C8 C9 179.3(3) . . . . ?
C7 C6 C5 C4 15.6(3) . . . . ?
C8 C9 C14 C13 -179.8(3) . . . . ?
C8 C9 C10 C11 -179.2(3) . . . . ?
C8 C6 C5 C4 -163.7(3) . . . . ?
C14 C9 C8 C6 -22.3(5) . . . . ?
C14 C9 C10 C11 1.5(4) . . . . ?
C14 C13 C12 C11 0.7(5) . . . . ?
C10 C9 C8 C6 158.5(3) . . . . ?
C10 C9 C14 C13 -0.5(4) . . . . ?
C10 C11 C12 C13 0.3(5) . . . . ?
C4 N1 C7 O1 -179.2(3) . . . . ?
C4 N1 C7 C6 2.6(3) . . . . ?
C4 N1 C1 C2 9.3(3) . . . . ?
C4 C3 C2 C1 -31.0(4) . . . . ?
C5 C6 C8 C9 -1.5(5) . . . . ?
C5 C4 C3 C2 148.9(3) . . . . ?
C12 C11 C10 C9 -1.5(5) . . . . ?
C1 N1 C7 O1 -21.2(5) . . . . ?
C1 N1 C7 C6 160.6(3) . . . . ?
C1 N1 C4 C5 -154.3(3) . . . . ?
C1 N1 C4 C3 -28.6(3) . . . . ?
C3 C4 C5 C6 -126.3(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_gupm0821
_database_code_depnum_ccdc_archive 'CCDC 1021204'
_audit_update_record             
;
2014-08-26 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_date             2014-08-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H14 Cl N O'
_chemical_formula_sum            'C14 H14 Cl N O'
_chemical_formula_weight         247.71
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.485(2)
_cell_length_b                   10.6501(11)
_cell_length_c                   13.4479(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.808(11)
_cell_angle_gamma                90.00
_cell_volume                     2480.9(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1770
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.7010
_cell_measurement_theta_min      5.7140
_exptl_absorpt_coefficient_mu    2.575
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4308
_diffrn_reflns_theta_full        69.82
_diffrn_reflns_theta_max         69.82
_diffrn_reflns_theta_min         5.11
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   39.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  150.0000 51

#__ type_ start__ end____ width___ exp.time_
  2 omega   36.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 49

#__ type_ start__ end____ width___ exp.time_
  3 omega   64.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   98.00  169.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -120.0000 71

#__ type_ start__ end____ width___ exp.time_
  5 omega  126.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -180.0000 52

#__ type_ start__ end____ width___ exp.time_
  6 omega  106.00  133.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  7 omega   86.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -30.0000 29

#__ type_ start__ end____ width___ exp.time_
  8 omega  129.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -30.0000 45

#__ type_ start__ end____ width___ exp.time_
  9 omega   96.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   58.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 11 omega   41.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
 12 omega   37.00  127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   19.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
 13 omega   40.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000   30.0000 77

#__ type_ start__ end____ width___ exp.time_
 14 omega   34.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 15 omega  -12.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   60.0000 62

#__ type_ start__ end____ width___ exp.time_
 16 omega  -32.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 17 omega  -63.00  -27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -60.0000 36

#__ type_ start__ end____ width___ exp.time_
 18 omega  -72.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000    0.0000 36

#__ type_ start__ end____ width___ exp.time_
 19 omega    1.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000 -180.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0776428000
_diffrn_orient_matrix_UB_12      -0.0628371000
_diffrn_orient_matrix_UB_13      0.0116457000
_diffrn_orient_matrix_UB_21      0.0059043000
_diffrn_orient_matrix_UB_22      -0.0802405000
_diffrn_orient_matrix_UB_23      -0.0939698000
_diffrn_orient_matrix_UB_31      0.0428510000
_diffrn_orient_matrix_UB_32      -0.1026373000
_diffrn_orient_matrix_UB_33      0.0665381000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1840
_reflns_number_total             2275
_reflns_odcompleteness_completeness 98.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0527
_refine_ls_restrained_S_all      1.130
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1518P)²+0.4120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1953
_refine_ls_wR_factor_ref         0.2273
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Others
 Fixed Sof: H10A(0.75) H10B(0.75) H10C(0.25) H10D(0.25) H11A(0.75) H11B(0.75)
 H11C(0.25) H11D(0.25) H14A(0.75) H14B(0.75) H14C(0.25) H14D(0.25) N1(0.75)
 C12(0.75) H12A(0.75) H12B(0.75) C13(0.75) H13(0.75) N1'(0.25) C12'(0.25)
 H12C(0.25) H12D(0.25) C13'(0.25) H13'(0.25)
3.a Ternary CH refined with riding coordinates:
 C13(H13), C13'(H13')
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10(H10C,H10D), C11(H11A,H11B), C11(H11C,H11D), C14(H14A,
 H14B), C14(H14C,H14D), C12(H12A,H12B), C12'(H12C,H12D)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.06737(5) 0.18110(8) 0.37120(5) 0.0824(4) Uani 1 d . . .
O1 O 0.13063(12) 0.4822(2) 0.63188(12) 0.0686(6) Uani 1 d D . .
C1 C 0.09714(17) 0.0963(3) 0.5940(2) 0.0678(7) Uani 1 d . . .
H1 H 0.0490 0.0747 0.5603 0.081 Uiso 1 calc . . R
C2 C 0.1295(2) 0.0247(3) 0.6742(3) 0.0830(9) Uani 1 d . . .
H2 H 0.1030 -0.0444 0.6943 0.100 Uiso 1 calc . . R
C3 C 0.2005(2) 0.0552(3) 0.7242(2) 0.0828(10) Uani 1 d . . .
H3 H 0.2227 0.0061 0.7777 0.099 Uiso 1 calc . . R
C4 C 0.23880(17) 0.1581(3) 0.6952(2) 0.0727(9) Uani 1 d . . .
H4 H 0.2867 0.1792 0.7300 0.087 Uiso 1 calc . . R
C5 C 0.20737(14) 0.2311(3) 0.61522(18) 0.0577(6) Uani 1 d . . .
H5 H 0.2341 0.3007 0.5961 0.069 Uiso 1 calc . . R
C6 C 0.13534(14) 0.2002(2) 0.56306(17) 0.0508(6) Uani 1 d . . .
C7 C 0.10343(13) 0.2742(3) 0.47435(17) 0.0526(6) Uani 1 d . . .
C8 C 0.10083(13) 0.3976(3) 0.46143(16) 0.0551(6) Uani 1 d D . .
C9 C 0.12291(15) 0.4946(2) 0.54179(17) 0.0586(6) Uani 1 d . . .
C10 C 0.1358(2) 0.7270(3) 0.5333(3) 0.0837(10) Uani 1 d . . .
H10A H 0.1825 0.7512 0.5764 0.100 Uiso 0.75 calc A 1 R
H10B H 0.0920 0.7349 0.5701 0.100 Uiso 0.75 calc A 1 R
H10C H 0.1165 0.7708 0.5881 0.100 Uiso 0.25 calc A 2 R
H10D H 0.1897 0.7061 0.5528 0.100 Uiso 0.25 calc A 2 R
C11 C 0.1245(3) 0.8041(4) 0.4378(3) 0.0947(11) Uani 1 d D . .
H11A H 0.0955 0.8800 0.4469 0.114 Uiso 0.75 calc B 1 R
H11B H 0.1738 0.8271 0.4177 0.114 Uiso 0.75 calc B 1 R
H11C H 0.1676 0.8596 0.4322 0.114 Uiso 0.25 calc B 2 R
H11D H 0.0767 0.8515 0.4303 0.114 Uiso 0.25 calc B 2 R
C14 C 0.07652(17) 0.4684(3) 0.36542(18) 0.0689(8) Uani 1 d . . .
H14A H 0.0212 0.4827 0.3550 0.083 Uiso 0.75 calc C 1 R
H14B H 0.0912 0.4238 0.3080 0.083 Uiso 0.75 calc C 1 R
H14C H 0.1169 0.4644 0.3227 0.083 Uiso 0.25 calc C 2 R
H14D H 0.0301 0.4313 0.3295 0.083 Uiso 0.25 calc C 2 R
N1 N 0.14179(19) 0.6002(3) 0.4941(2) 0.0590(7) Uani 0.75 d D 1 .
C12 C 0.0802(4) 0.7201(5) 0.3613(4) 0.0825(14) Uani 0.75 d D 1 .
H12A H 0.0837 0.7483 0.2934 0.099 Uiso 0.75 calc D 1 R
H12B H 0.0263 0.7140 0.3709 0.099 Uiso 0.75 calc D 1 R
C13 C 0.1225(2) 0.5959(4) 0.3842(3) 0.0575(8) Uani 0.75 d D 1 .
H13 H 0.1697 0.5936 0.3524 0.069 Uiso 0.75 calc D 1 R
N1' N 0.0853(6) 0.6040(9) 0.5006(7) 0.063(2) Uani 0.25 d D 2 .
C12' C 0.1211(11) 0.679(2) 0.3569(11) 0.086(4) Uani 0.25 d D 2 .
H12C H 0.1066 0.7060 0.2879 0.103 Uiso 0.25 calc D 2 R
H12D H 0.1704 0.6363 0.3626 0.103 Uiso 0.25 calc D 2 R
C13' C 0.0618(6) 0.6002(11) 0.3909(8) 0.064(3) Uani 0.25 d D 2 .
H13' H 0.0088 0.6286 0.3692 0.077 Uiso 0.25 calc D 2 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
Cl1 C7 1.752(2) . ?
O1 C9 1.208(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.377(5) . ?
C1 C6 1.385(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.369(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.395(3) . ?
C6 C7 1.475(3) . ?
C7 C8 1.325(4) . ?
C8 C9 1.507(3) . ?
C8 C14 1.506(3) . ?
C9 N1 1.357(4) . ?
C9 N1' 1.414(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C10 H10D 0.9700 . ?
C10 C11 1.514(5) . ?
C10 N1 1.459(4) . ?
C10 N1' 1.607(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C11 H11D 0.9700 . ?
C11 C12 1.498(7) . ?
C11 C12' 1.71(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C14 H14D 0.9700 . ?
C14 C13 1.582(5) . ?
C14 C13' 1.476(12) . ?
N1 C13 1.471(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.526(6) . ?
C13 H13 0.9800 . ?
N1' C13' 1.477(14) . ?
C12' H12C 0.9700 . ?
C12' H12D 0.9700 . ?
C12' C13' 1.458(19) . ?
C13' H13' 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 H1 119.5 . . ?
C2 C1 C6 120.9(3) . . ?
C6 C1 H1 119.5 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.7(3) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 118.5(2) . . ?
C1 C6 C7 121.7(2) . . ?
C5 C6 C7 119.8(2) . . ?
C6 C7 Cl1 113.18(19) . . ?
C8 C7 Cl1 117.09(18) . . ?
C8 C7 C6 129.7(2) . . ?
C7 C8 C9 125.8(2) . . ?
C7 C8 C14 127.6(2) . . ?
C14 C8 C9 106.7(2) . . ?
O1 C9 C8 128.8(3) . . ?
O1 C9 N1 124.3(3) . . ?
O1 C9 N1' 117.7(4) . . ?
N1 C9 C8 106.5(2) . . ?
N1 C9 N1' 42.5(4) . . ?
N1' C9 C8 103.0(4) . . ?
H10A C10 H10B 109.3 . . ?
H10A C10 H10C 76.7 . . ?
H10A C10 H10D 35.9 . . ?
H10B C10 H10C 36.0 . . ?
H10B C10 H10D 133.4 . . ?
H10C C10 H10D 109.2 . . ?
C11 C10 H10A 111.4 . . ?
C11 C10 H10B 111.4 . . ?
C11 C10 H10C 111.4 . . ?
C11 C10 H10D 111.4 . . ?
C11 C10 N1' 101.9(4) . . ?
N1 C10 H10A 111.4 . . ?
N1 C10 H10B 111.4 . . ?
N1 C10 H10C 140.2 . . ?
N1 C10 H10D 76.7 . . ?
N1 C10 C11 101.7(3) . . ?
N1 C10 N1' 37.9(3) . . ?
N1' C10 H10A 140.0 . . ?
N1' C10 H10B 76.6 . . ?
N1' C10 H10C 111.4 . . ?
N1' C10 H10D 111.4 . . ?
C10 C11 H11A 110.8 . . ?
C10 C11 H11B 110.8 . . ?
C10 C11 H11C 112.5 . . ?
C10 C11 H11D 112.5 . . ?
C10 C11 C12' 96.2(6) . . ?
H11A C11 H11B 108.9 . . ?
H11A C11 H11C 85.8 . . ?
H11A C11 H11D 28.7 . . ?
H11B C11 H11C 24.9 . . ?
H11B C11 H11D 128.7 . . ?
H11C C11 H11D 110.0 . . ?
C12 C11 C10 104.8(3) . . ?
C12 C11 H11A 110.8 . . ?
C12 C11 H11B 110.8 . . ?
C12 C11 H11C 130.2 . . ?
C12 C11 H11D 83.2 . . ?
C12 C11 C12' 29.6(6) . . ?
C12' C11 H11A 138.8 . . ?
C12' C11 H11B 88.5 . . ?
C12' C11 H11C 112.5 . . ?
C12' C11 H11D 112.5 . . ?
C8 C14 H14A 111.3 . . ?
C8 C14 H14B 111.3 . . ?
C8 C14 H14C 110.0 . . ?
C8 C14 H14D 110.0 . . ?
C8 C14 C13 102.4(2) . . ?
H14A C14 H14B 109.2 . . ?
H14A C14 H14C 135.5 . . ?
H14A C14 H14D 40.7 . . ?
H14B C14 H14C 38.3 . . ?
H14B C14 H14D 72.5 . . ?
H14C C14 H14D 108.4 . . ?
C13 C14 H14A 111.3 . . ?
C13 C14 H14B 111.3 . . ?
C13 C14 H14C 74.7 . . ?
C13 C14 H14D 143.3 . . ?
C13' C14 C8 108.4(5) . . ?
C13' C14 H14A 71.4 . . ?
C13' C14 H14B 136.3 . . ?
C13' C14 H14C 110.0 . . ?
C13' C14 H14D 110.0 . . ?
C13' C14 C13 41.1(5) . . ?
C9 N1 C10 124.2(3) . . ?
C9 N1 C13 114.3(3) . . ?
C10 N1 C13 111.9(3) . . ?
C11 C12 H12A 111.6 . . ?
C11 C12 H12B 111.6 . . ?
C11 C12 C13 100.8(4) . . ?
H12A C12 H12B 109.4 . . ?
C13 C12 H12A 111.6 . . ?
C13 C12 H12B 111.6 . . ?
C14 C13 H13 110.4 . . ?
N1 C13 C14 103.2(3) . . ?
N1 C13 C12 102.4(3) . . ?
N1 C13 H13 110.4 . . ?
C12 C13 C14 119.3(3) . . ?
C12 C13 H13 110.4 . . ?
C9 N1' C10 110.8(7) . . ?
C9 N1' C13' 114.8(8) . . ?
C13' N1' C10 111.3(8) . . ?
C11 C12' H12C 111.3 . . ?
C11 C12' H12D 111.3 . . ?
H12C C12' H12D 109.2 . . ?
C13' C12' C11 102.3(11) . . ?
C13' C12' H12C 111.3 . . ?
C13' C12' H12D 111.3 . . ?
C14 C13' N1' 103.0(7) . . ?
C14 C13' H13' 114.3 . . ?
N1' C13' H13' 114.3 . . ?
C12' C13' C14 108.9(12) . . ?
C12' C13' N1' 100.6(11) . . ?
C12' C13' H13' 114.3 . . ?

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 C7 C8 C9 175.01(19) . . . . ?
Cl1 C7 C8 C14 -5.6(3) . . . . ?
O1 C9 N1 C10 -32.8(5) . . . . ?
O1 C9 N1 C13 -176.3(3) . . . . ?
O1 C9 N1' C10 66.3(7) . . . . ?
O1 C9 N1' C13' -166.6(7) . . . . ?
C1 C2 C3 C4 1.0(5) . . . . ?
C1 C6 C7 Cl1 -44.6(3) . . . . ?
C1 C6 C7 C8 137.9(3) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
C2 C1 C6 C7 176.9(3) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C1 0.4(4) . . . . ?
C4 C5 C6 C7 -176.9(2) . . . . ?
C5 C6 C7 Cl1 132.6(2) . . . . ?
C5 C6 C7 C8 -44.9(4) . . . . ?
C6 C1 C2 C3 -0.4(5) . . . . ?
C6 C7 C8 C9 -7.6(4) . . . . ?
C6 C7 C8 C14 171.7(2) . . . . ?
C7 C8 C9 O1 -17.1(4) . . . . ?
C7 C8 C9 N1 156.1(3) . . . . ?
C7 C8 C9 N1' -160.1(4) . . . . ?
C7 C8 C14 C13 -153.3(3) . . . . ?
C7 C8 C14 C13' 164.3(5) . . . . ?
C8 C9 N1 C10 153.6(3) . . . . ?
C8 C9 N1 C13 10.1(3) . . . . ?
C8 C9 N1' C10 -145.7(4) . . . . ?
C8 C9 N1' C13' -18.6(9) . . . . ?
C8 C14 C13 N1 -19.8(3) . . . . ?
C8 C14 C13 C12 -132.4(3) . . . . ?
C8 C14 C13' N1' 5.2(8) . . . . ?
C8 C14 C13' C12' 111.4(9) . . . . ?
C9 C8 C14 C13 26.1(3) . . . . ?
C9 C8 C14 C13' -16.2(5) . . . . ?
C9 N1 C13 C14 6.3(3) . . . . ?
C9 N1 C13 C12 130.9(4) . . . . ?
C9 N1' C13' C14 8.8(11) . . . . ?
C9 N1' C13' C12' -103.6(13) . . . . ?
C10 C11 C12 C13 -43.2(5) . . . . ?
C10 C11 C12' C13' 52.9(12) . . . . ?
C10 N1 C13 C14 -141.6(3) . . . . ?
C10 N1 C13 C12 -17.1(5) . . . . ?
C10 N1' C13' C14 135.8(7) . . . . ?
C10 N1' C13' C12' 23.4(13) . . . . ?
C11 C10 N1 C9 -153.3(3) . . . . ?
C11 C10 N1 C13 -9.1(4) . . . . ?
C11 C10 N1' C9 140.5(5) . . . . ?
C11 C10 N1' C13' 11.4(8) . . . . ?
C11 C12 C13 C14 149.1(3) . . . . ?
C11 C12 C13 N1 36.1(4) . . . . ?
C11 C12' C13' C14 -153.0(8) . . . . ?
C11 C12' C13' N1' -45.2(13) . . . . ?
C14 C8 C9 O1 163.4(3) . . . . ?
C14 C8 C9 N1 -23.4(3) . . . . ?
C14 C8 C9 N1' 20.4(5) . . . . ?
N1 C9 N1' C10 -45.3(5) . . . . ?
N1 C9 N1' C13' 81.9(8) . . . . ?
N1 C10 C11 C12 32.6(4) . . . . ?
N1 C10 C11 C12' 3.8(7) . . . . ?
N1 C10 N1' C9 46.6(5) . . . . ?
N1 C10 N1' C13' -82.4(8) . . . . ?
C12 C11 C12' C13' -56.3(10) . . . . ?
C13 C14 C13' N1' -82.8(8) . . . . ?
C13 C14 C13' C12' 23.4(7) . . . . ?
N1' C9 N1 C10 62.3(6) . . . . ?
N1' C9 N1 C13 -81.1(6) . . . . ?
N1' C10 C11 C12 -6.1(5) . . . . ?
N1' C10 C11 C12' -34.9(7) . . . . ?
N1' C10 N1 C9 -58.9(6) . . . . ?
N1' C10 N1 C13 85.3(6) . . . . ?
C12' C11 C12 C13 33.1(10) . . . . ?
C13' C14 C13 N1 84.0(7) . . . . ?
C13' C14 C13 C12 -28.7(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
