# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_71a_re_a
_database_code_depnum_ccdc_archive 'CCDC 1944051'
loop_
_audit_author_name
_audit_author_address
'Dong Won Kim'
;Yeungnam University
South Korea
;
_audit_update_record             
;
2019-07-30 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'Methyl (E)-3-(2-((1H-pyrazol-1-yl)methyl)phenyl)acrylate'
_chemical_name_common            ?
_chemical_melting_point          331
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N2 O2'
_chemical_formula_weight         242.27

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'

_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                   8.868(5)
_cell_length_b                   8.948(5)
_cell_length_c                   10.107(6)
_cell_angle_alpha                84.918(4)
_cell_angle_beta                 66.058(4)
_cell_angle_gamma                61.274(4)
_cell_volume                     637.1(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3461
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      27.74

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6507
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Photon 100 CMOS detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12629
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.790
_diffrn_reflns_theta_max         28.449
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2984
_reflns_number_gt                1783
_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       'Bruker APEXIII'
_computing_cell_refinement       'Bruker APEXIII'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_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)+(0.0519P)²+0.1623P] 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         2984
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.0664
_refine_ls_wR_factor_ref         0.1556
_refine_ls_wR_factor_gt          0.1336
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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_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
N1 N 0.0012(2) 0.5777(2) 0.64751(17) 0.0491(4) Uani 1 1 d . . . . .
C1 C 0.7807(4) -0.1226(4) 0.0755(3) 0.1001(10) Uani 1 1 d . . . . .
H1A H 0.670528 -0.112470 0.066088 0.150 Uiso 1 1 calc R U . . .
H1B H 0.866422 -0.243640 0.075643 0.150 Uiso 1 1 calc R U . . .
H1C H 0.846833 -0.078567 -0.006942 0.150 Uiso 1 1 calc R U . . .
O1 O 0.7189(2) -0.0234(2) 0.21135(19) 0.0890(6) Uani 1 1 d . . . . .
O2 O 1.0170(2) -0.1353(2) 0.1790(2) 0.0938(6) Uani 1 1 d . . . . .
N2 N -0.0634(3) 0.7431(2) 0.6219(2) 0.0603(5) Uani 1 1 d . . . . .
C2 C 0.8516(3) -0.0384(3) 0.2500(2) 0.0615(6) Uani 1 1 d . . . . .
C5 C 0.5109(3) 0.2965(3) 0.5957(2) 0.0466(5) Uani 1 1 d . . . . .
C4 C 0.5946(3) 0.1811(3) 0.4608(2) 0.0528(5) Uani 1 1 d . . . . .
H4 H 0.509418 0.186273 0.424002 0.063 Uiso 1 1 calc R U . . .
C3 C 0.7750(3) 0.0716(3) 0.3855(2) 0.0608(6) Uani 1 1 d . . . . .
H3 H 0.861812 0.063290 0.421811 0.073 Uiso 1 1 calc R U . . .
C8 C 0.3546(3) 0.5183(3) 0.8503(2) 0.0638(6) Uani 1 1 d . . . . .
H8 H 0.301386 0.594488 0.936080 0.077 Uiso 1 1 calc R U . . .
C7 C 0.5396(3) 0.3884(3) 0.7993(2) 0.0648(6) Uani 1 1 d . . . . .
H7 H 0.613642 0.373298 0.851004 0.078 Uiso 1 1 calc R U . . .
C6 C 0.6175(3) 0.2800(3) 0.6728(2) 0.0587(6) Uani 1 1 d . . . . .
H6 H 0.746069 0.192351 0.637393 0.070 Uiso 1 1 calc R U . . .
C9 C 0.2461(3) 0.5377(3) 0.7760(2) 0.0557(6) Uani 1 1 d . . . . .
H9 H 0.118624 0.627669 0.811633 0.067 Uiso 1 1 calc R U . . .
C10 C 0.3203(3) 0.4281(3) 0.6505(2) 0.0453(5) Uani 1 1 d . . . . .
C11 C 0.1998(3) 0.4499(3) 0.5703(2) 0.0534(5) Uani 1 1 d . . . . .
H11A H 0.251675 0.483745 0.473264 0.064 Uiso 1 1 calc R U . . .
H11B H 0.208777 0.337828 0.554311 0.064 Uiso 1 1 calc R U . . .
C12 C -0.1339(3) 0.5539(3) 0.7537(2) 0.0591(6) Uani 1 1 d . . . . .
H12 H -0.119829 0.448606 0.790251 0.071 Uiso 1 1 calc R U . . .
C13 C -0.2958(3) 0.7093(3) 0.7994(2) 0.0634(6) Uani 1 1 d . . . . .
H13 H -0.416722 0.734821 0.872965 0.076 Uiso 1 1 calc R U . . .
C14 C -0.2447(3) 0.8210(3) 0.7152(3) 0.0632(6) Uani 1 1 d . . . . .
H14 H -0.329307 0.940028 0.722857 0.076 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
N1 C12 1.339(3) . ?
N1 N2 1.350(2) . ?
N1 C11 1.458(2) . ?
C1 O1 1.453(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
O1 C2 1.330(3) . ?
O2 C2 1.205(3) . ?
N2 C14 1.329(3) . ?
C2 C3 1.465(3) . ?
C5 C6 1.402(3) . ?
C5 C10 1.412(3) . ?
C5 C4 1.472(3) . ?
C4 C3 1.317(3) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
C8 C7 1.377(3) . ?
C8 C9 1.386(3) . ?
C8 H8 0.9500 . ?
C7 C6 1.383(3) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
C9 C10 1.388(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.520(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.365(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 N2 112.02(17) . . ?
C12 N1 C11 126.97(19) . . ?
N2 N1 C11 120.90(17) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 O1 C1 117.52(19) . . ?
C14 N2 N1 103.87(18) . . ?
O2 C2 O1 121.9(2) . . ?
O2 C2 C3 124.9(2) . . ?
O1 C2 C3 113.21(18) . . ?
C6 C5 C10 118.14(19) . . ?
C6 C5 C4 121.30(19) . . ?
C10 C5 C4 120.56(18) . . ?
C3 C4 C5 127.0(2) . . ?
C3 C4 H4 116.5 . . ?
C5 C4 H4 116.5 . . ?
C4 C3 C2 124.9(2) . . ?
C4 C3 H3 117.6 . . ?
C2 C3 H3 117.6 . . ?
C7 C8 C9 119.8(2) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C7 C6 119.9(2) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C6 C5 121.5(2) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C8 C9 C10 121.3(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C5 119.41(18) . . ?
C9 C10 C11 120.81(18) . . ?
C5 C10 C11 119.78(17) . . ?
N1 C11 C10 113.78(16) . . ?
N1 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
N1 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
N1 C12 C13 107.2(2) . . ?
N1 C12 H12 126.4 . . ?
C13 C12 H12 126.4 . . ?
C12 C13 C14 104.6(2) . . ?
C12 C13 H13 127.7 . . ?
C14 C13 H13 127.7 . . ?
N2 C14 C13 112.3(2) . . ?
N2 C14 H14 123.9 . . ?
C13 C14 H14 123.9 . . ?

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
C12 N1 N2 C14 -0.7(2) . . . . ?
C11 N1 N2 C14 -177.14(18) . . . . ?
C1 O1 C2 O2 -2.8(4) . . . . ?
C1 O1 C2 C3 177.8(2) . . . . ?
C6 C5 C4 C3 -10.8(3) . . . . ?
C10 C5 C4 C3 168.8(2) . . . . ?
C5 C4 C3 C2 -178.8(2) . . . . ?
O2 C2 C3 C4 177.9(2) . . . . ?
O1 C2 C3 C4 -2.8(3) . . . . ?
C9 C8 C7 C6 1.3(4) . . . . ?
C8 C7 C6 C5 -1.4(3) . . . . ?
C10 C5 C6 C7 0.2(3) . . . . ?
C4 C5 C6 C7 179.8(2) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C8 C9 C10 C5 -1.3(3) . . . . ?
C8 C9 C10 C11 179.69(19) . . . . ?
C6 C5 C10 C9 1.1(3) . . . . ?
C4 C5 C10 C9 -178.45(18) . . . . ?
C6 C5 C10 C11 -179.83(18) . . . . ?
C4 C5 C10 C11 0.6(3) . . . . ?
C12 N1 C11 C10 -83.7(3) . . . . ?
N2 N1 C11 C10 92.2(2) . . . . ?
C9 C10 C11 N1 -7.5(3) . . . . ?
C5 C10 C11 N1 173.51(18) . . . . ?
N2 N1 C12 C13 0.8(2) . . . . ?
C11 N1 C12 C13 176.96(19) . . . . ?
N1 C12 C13 C14 -0.5(3) . . . . ?
N1 N2 C14 C13 0.4(3) . . . . ?
C12 C13 C14 N2 0.1(3) . . . . ?

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.035




















_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/EtOAc'
####################################################################### 
# 
# 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_105_re_a
_database_code_depnum_ccdc_archive 'CCDC 1944054'
loop_
_audit_author_name
_audit_author_address
'Dong Won Kim'
;Yeungnam University
South Korea
;
_audit_update_record             
;
2019-07-30 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'Methyl (E)-3-(2-((1H-indazol-1-yl)methyl)phenyl)acrylate'
_chemical_name_common            ?
_chemical_melting_point          396
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33

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'

_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                   7.423(5)
_cell_length_b                   10.929(7)
_cell_length_c                   10.931(7)
_cell_angle_alpha                106.755(4)
_cell_angle_beta                 107.442(4)
_cell_angle_gamma                108.018(4)
_cell_volume                     730.2(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3500
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      27.07

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6159
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Photon 100 CMOS detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16840
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.979
_diffrn_reflns_theta_max         28.489
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3454
_reflns_number_gt                2354
_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       'Bruker APEXIII'
_computing_cell_refinement       'Bruker APEXIII'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_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)+(0.0511P)²+0.1263P] 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         3454
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1104
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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_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 0.4932(2) 0.58520(13) 0.17505(13) 0.0455(4) Uani 1 1 d . . . . .
C1 C 0.2579(3) 0.3092(2) 0.02096(18) 0.0460(5) Uani 1 1 d . . . . .
H1A H 0.183517 0.205920 -0.016071 0.069 Uiso 1 1 calc R U . . .
H1B H 0.331403 0.333367 -0.035804 0.069 Uiso 1 1 calc R U . . .
H1C H 0.157136 0.350204 0.016342 0.069 Uiso 1 1 calc R U . . .
N1 N 0.7609(2) 0.16582(14) 0.60839(14) 0.0324(4) Uani 1 1 d . . . . .
N2 N 0.9099(2) 0.12867(15) 0.58141(15) 0.0376(4) Uani 1 1 d . . . . .
O2 O 0.40806(19) 0.36563(13) 0.16627(12) 0.0388(3) Uani 1 1 d . . . . .
C2 C 0.5184(3) 0.50760(18) 0.23179(18) 0.0320(4) Uani 1 1 d . . . . .
C5 C 0.8380(2) 0.51857(17) 0.59065(16) 0.0284(4) Uani 1 1 d . . . . .
C4 C 0.6882(3) 0.47551(18) 0.44514(17) 0.0306(4) Uani 1 1 d . . . . .
H4 H 0.592917 0.377974 0.393727 0.037 Uiso 1 1 calc R U . . .
C3 C 0.6718(3) 0.55835(18) 0.37774(17) 0.0329(4) Uani 1 1 d . . . . .
H3 H 0.765190 0.656379 0.427150 0.039 Uiso 1 1 calc R U . . .
C7 C 1.1164(3) 0.70325(19) 0.81625(18) 0.0384(4) Uani 1 1 d . . . . .
H7 H 1.206776 0.800763 0.874739 0.046 Uiso 1 1 calc R U . . .
C6 C 0.9761(3) 0.66170(18) 0.67890(18) 0.0359(4) Uani 1 1 d . . . . .
H6 H 0.973260 0.731418 0.643753 0.043 Uiso 1 1 calc R U . . .
C8 C 1.1247(3) 0.60267(19) 0.86812(18) 0.0377(4) Uani 1 1 d . . . . .
H8 H 1.221396 0.630716 0.961951 0.045 Uiso 1 1 calc R U . . .
C9 C 0.9915(3) 0.46124(18) 0.78269(17) 0.0339(4) Uani 1 1 d . . . . .
H9 H 0.998278 0.392521 0.818625 0.041 Uiso 1 1 calc R U . . .
C10 C 0.8471(3) 0.41709(17) 0.64454(16) 0.0279(4) Uani 1 1 d . . . . .
C11 C 0.6999(3) 0.26021(17) 0.55346(17) 0.0341(4) Uani 1 1 d . . . . .
H11A H 0.557117 0.244223 0.545024 0.041 Uiso 1 1 calc R U . . .
H11B H 0.694323 0.235631 0.457435 0.041 Uiso 1 1 calc R U . . .
C12 C 0.6897(3) 0.10390(16) 0.68750(16) 0.0291(4) Uani 1 1 d . . . . .
C13 C 0.5401(3) 0.11135(17) 0.73852(17) 0.0342(4) Uani 1 1 d . . . . .
H13 H 0.469025 0.168049 0.722496 0.041 Uiso 1 1 calc R U . . .
C14 C 0.5013(3) 0.03221(19) 0.81316(18) 0.0386(4) Uani 1 1 d . . . . .
H14 H 0.400112 0.034262 0.849214 0.046 Uiso 1 1 calc R U . . .
C15 C 0.6068(3) -0.05217(19) 0.83815(17) 0.0379(5) Uani 1 1 d . . . . .
H15 H 0.573978 -0.105816 0.889562 0.045 Uiso 1 1 calc R U . . .
C16 C 0.7552(3) -0.05790(17) 0.78959(17) 0.0352(4) Uani 1 1 d . . . . .
H16 H 0.826724 -0.113825 0.807658 0.042 Uiso 1 1 calc R U . . .
C17 C 0.7991(3) 0.02124(17) 0.71214(16) 0.0312(4) Uani 1 1 d . . . . .
C18 C 0.9326(3) 0.04261(19) 0.64311(18) 0.0372(4) Uani 1 1 d . . . . .
H18 H 1.026689 0.000506 0.641244 0.045 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2128(19) . ?
C1 O2 1.447(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N1 C12 1.370(2) . ?
N1 N2 1.370(2) . ?
N1 C11 1.454(2) . ?
N2 C18 1.328(2) . ?
O2 C2 1.346(2) . ?
C2 C3 1.470(2) . ?
C5 C6 1.405(2) . ?
C5 C10 1.407(2) . ?
C5 C4 1.474(2) . ?
C4 C3 1.333(2) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
C7 C8 1.383(3) . ?
C7 C6 1.386(2) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.381(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.397(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.526(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.397(3) . ?
C12 C17 1.418(2) . ?
C13 C14 1.375(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.415(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.369(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.409(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.419(3) . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C12 N1 N2 111.56(13) . . ?
C12 N1 C11 129.10(15) . . ?
N2 N1 C11 119.34(14) . . ?
C18 N2 N1 106.03(14) . . ?
C2 O2 C1 115.83(13) . . ?
O1 C2 O2 122.96(16) . . ?
O1 C2 C3 123.68(16) . . ?
O2 C2 C3 113.36(13) . . ?
C6 C5 C10 118.27(15) . . ?
C6 C5 C4 120.94(15) . . ?
C10 C5 C4 120.79(15) . . ?
C3 C4 C5 127.16(16) . . ?
C3 C4 H4 116.4 . . ?
C5 C4 H4 116.4 . . ?
C4 C3 C2 124.12(16) . . ?
C4 C3 H3 117.9 . . ?
C2 C3 H3 117.9 . . ?
C8 C7 C6 119.99(16) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C6 C5 121.32(16) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C9 C8 C7 119.61(16) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 121.40(16) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C5 119.40(15) . . ?
C9 C10 C11 120.16(14) . . ?
C5 C10 C11 120.44(14) . . ?
N1 C11 C10 113.93(14) . . ?
N1 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
N1 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
N1 C12 C13 131.20(15) . . ?
N1 C12 C17 106.34(15) . . ?
C13 C12 C17 122.45(15) . . ?
C14 C13 C12 116.41(16) . . ?
C14 C13 H13 121.8 . . ?
C12 C13 H13 121.8 . . ?
C13 C14 C15 122.29(18) . . ?
C13 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C16 C15 C14 121.19(17) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 118.31(16) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
C16 C17 C12 119.33(16) . . ?
C16 C17 C18 136.34(16) . . ?
C12 C17 C18 104.32(15) . . ?
N2 C18 C17 111.74(16) . . ?
N2 C18 H18 124.1 . . ?
C17 C18 H18 124.1 . . ?

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
C12 N1 N2 C18 0.21(17) . . . . ?
C11 N1 N2 C18 -179.73(14) . . . . ?
C1 O2 C2 O1 1.2(2) . . . . ?
C1 O2 C2 C3 -178.56(14) . . . . ?
C6 C5 C4 C3 4.3(3) . . . . ?
C10 C5 C4 C3 -175.34(17) . . . . ?
C5 C4 C3 C2 179.78(16) . . . . ?
O1 C2 C3 C4 173.91(18) . . . . ?
O2 C2 C3 C4 -6.4(2) . . . . ?
C8 C7 C6 C5 1.1(3) . . . . ?
C10 C5 C6 C7 -0.8(3) . . . . ?
C4 C5 C6 C7 179.51(16) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C8 C9 C10 C5 0.5(3) . . . . ?
C8 C9 C10 C11 -179.13(16) . . . . ?
C6 C5 C10 C9 0.0(2) . . . . ?
C4 C5 C10 C9 179.69(15) . . . . ?
C6 C5 C10 C11 179.68(15) . . . . ?
C4 C5 C10 C11 -0.6(2) . . . . ?
C12 N1 C11 C10 97.4(2) . . . . ?
N2 N1 C11 C10 -82.63(19) . . . . ?
C9 C10 C11 N1 -15.0(2) . . . . ?
C5 C10 C11 N1 165.35(15) . . . . ?
N2 N1 C12 C13 -179.76(16) . . . . ?
C11 N1 C12 C13 0.2(3) . . . . ?
N2 N1 C12 C17 -0.32(17) . . . . ?
C11 N1 C12 C17 179.62(14) . . . . ?
N1 C12 C13 C14 178.51(16) . . . . ?
C17 C12 C13 C14 -0.9(2) . . . . ?
C12 C13 C14 C15 0.3(2) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C14 C15 C16 C17 -0.8(2) . . . . ?
C15 C16 C17 C12 0.2(2) . . . . ?
C15 C16 C17 C18 -178.60(19) . . . . ?
N1 C12 C17 C16 -178.85(14) . . . . ?
C13 C12 C17 C16 0.7(2) . . . . ?
N1 C12 C17 C18 0.29(17) . . . . ?
C13 C12 C17 C18 179.79(15) . . . . ?
N1 N2 C18 C17 -0.02(19) . . . . ?
C16 C17 C18 N2 178.74(18) . . . . ?
C12 C17 C18 N2 -0.17(19) . . . . ?

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.039




















_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/EtOAc'
