# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_bww17349a
_database_code_depnum_ccdc_archive 'CCDC 1572105'
_audit_update_record             
;
2017-11-17 deposited with the CCDC.
2018-04-19 downloaded from the CCDC.
;
_audit_creation_date             2017-07-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H10 N2 O'
_chemical_formula_sum            'C14 H10 N2 O'
_chemical_formula_weight         222.24
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.105(2)
_cell_length_b                   7.6772(15)
_cell_length_c                   11.507(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.73(3)
_cell_angle_gamma                90
_cell_volume                     1059.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3240
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4623
_cell_measurement_theta_min      1.6978
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7289
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.460
_diffrn_reflns_theta_min         3.150
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2133
_reflns_number_total             2402
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2402
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0617
_refine_ls_restrained_S_all      1.152
_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)+(0.0587P)²+0.3790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1437
_refine_ls_wR_factor_ref         0.1500
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.91173(10) 0.23515(16) 0.06130(10) 0.0324(3) Uani 1 1 d . . . . .
N1 N 0.75439(12) 0.0010(2) 0.31446(12) 0.0298(3) Uani 1 1 d . . . . .
N2 N 0.91790(11) 0.09095(18) 0.23671(12) 0.0250(3) Uani 1 1 d . . . . .
C1 C 0.69105(14) 0.0794(2) 0.21824(14) 0.0278(4) Uani 1 1 d . . . . .
C2 C 0.57429(15) 0.0789(3) 0.21257(16) 0.0361(4) Uani 1 1 d . . . . .
H2 H 0.5401 0.0223 0.2719 0.043 Uiso 1 1 calc R . . . .
C3 C 0.50962(15) 0.1605(3) 0.12097(18) 0.0413(5) Uani 1 1 d . . . . .
H3 H 0.4308 0.1621 0.1183 0.050 Uiso 1 1 calc R . . . .
C4 C 0.55892(16) 0.2410(3) 0.03195(18) 0.0400(5) Uani 1 1 d . . . . .
H4 H 0.5134 0.2960 -0.0312 0.048 Uiso 1 1 calc R . . . .
C5 C 0.67261(15) 0.2411(2) 0.03510(15) 0.0323(4) Uani 1 1 d . . . . .
H5 H 0.7056 0.2957 -0.0258 0.039 Uiso 1 1 calc R . . . .
C6 C 0.74011(13) 0.1603(2) 0.12862(14) 0.0256(4) Uani 1 1 d . . . . .
C7 C 0.86137(14) 0.1677(2) 0.13506(14) 0.0251(4) Uani 1 1 d . . . . .
C8 C 0.86083(14) 0.0116(2) 0.31887(14) 0.0282(4) Uani 1 1 d . . . . .
H8 H 0.9045 -0.0399 0.3847 0.034 Uiso 1 1 calc R . . . .
C9 C 1.03828(13) 0.0985(2) 0.25959(14) 0.0249(4) Uani 1 1 d . . . . .
C10 C 1.10217(14) 0.0336(2) 0.17768(15) 0.0288(4) Uani 1 1 d . . . . .
H10 H 1.0675 -0.0134 0.1055 0.035 Uiso 1 1 calc R . . . .
C11 C 1.21709(15) 0.0385(2) 0.20292(16) 0.0333(4) Uani 1 1 d . . . . .
H11 H 1.2617 -0.0045 0.1473 0.040 Uiso 1 1 calc R . . . .
C12 C 1.26786(15) 0.1057(2) 0.30861(17) 0.0361(4) Uani 1 1 d . . . . .
H12 H 1.3469 0.1089 0.3250 0.043 Uiso 1 1 calc R . . . .
C13 C 1.20351(15) 0.1682(2) 0.39041(16) 0.0341(4) Uani 1 1 d . . . . .
H13 H 1.2384 0.2128 0.4633 0.041 Uiso 1 1 calc R . . . .
C14 C 1.08792(14) 0.1656(2) 0.36575(15) 0.0288(4) Uani 1 1 d . . . . .
H14 H 1.0434 0.2094 0.4211 0.035 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 1.225(2) . ?
N1 C1 1.395(2) . ?
N1 C8 1.285(2) . ?
N2 C7 1.403(2) . ?
N2 C8 1.385(2) . ?
N2 C9 1.447(2) . ?
C1 C2 1.406(2) . ?
C1 C6 1.403(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.376(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.397(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.372(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.405(2) . ?
C6 C7 1.461(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(2) . ?
C9 C14 1.386(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(2) . ?
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
C8 N1 C1 116.42(15) . . ?
C7 N2 C9 120.09(13) . . ?
C8 N2 C7 121.45(14) . . ?
C8 N2 C9 118.43(13) . . ?
N1 C1 C2 118.50(16) . . ?
N1 C1 C6 122.18(15) . . ?
C6 C1 C2 119.31(16) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.93(17) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.51(17) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.47(18) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.86(17) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 119.91(15) . . ?
C1 C6 C7 120.12(15) . . ?
C5 C6 C7 119.91(15) . . ?
O1 C7 N2 121.53(15) . . ?
O1 C7 C6 124.87(15) . . ?
N2 C7 C6 113.59(14) . . ?
N1 C8 N2 126.19(16) . . ?
N1 C8 H8 116.9 . . ?
N2 C8 H8 116.9 . . ?
C10 C9 N2 120.08(15) . . ?
C14 C9 N2 118.80(15) . . ?
C14 C9 C10 121.08(15) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 118.93(16) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.60(17) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.09(16) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 119.92(16) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 C13 119.36(16) . . ?
C9 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?

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
N1 C1 C2 C3 177.69(18) . . . . ?
N1 C1 C6 C5 -178.43(16) . . . . ?
N1 C1 C6 C7 -1.2(2) . . . . ?
N2 C9 C10 C11 -178.45(14) . . . . ?
N2 C9 C14 C13 177.87(15) . . . . ?
C1 N1 C8 N2 -1.0(3) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C1 C6 C7 O1 179.92(16) . . . . ?
C1 C6 C7 N2 -1.0(2) . . . . ?
C2 C1 C6 C5 0.6(2) . . . . ?
C2 C1 C6 C7 177.81(15) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C4 C5 C6 C7 -177.04(16) . . . . ?
C5 C6 C7 O1 -2.9(3) . . . . ?
C5 C6 C7 N2 176.25(15) . . . . ?
C6 C1 C2 C3 -1.4(3) . . . . ?
C7 N2 C8 N1 -1.3(3) . . . . ?
C7 N2 C9 C10 -56.5(2) . . . . ?
C7 N2 C9 C14 125.66(17) . . . . ?
C8 N1 C1 C2 -176.84(16) . . . . ?
C8 N1 C1 C6 2.2(2) . . . . ?
C8 N2 C7 O1 -178.67(15) . . . . ?
C8 N2 C7 C6 2.2(2) . . . . ?
C8 N2 C9 C10 125.43(17) . . . . ?
C8 N2 C9 C14 -52.4(2) . . . . ?
C9 N2 C7 O1 3.4(2) . . . . ?
C9 N2 C7 C6 -175.79(13) . . . . ?
C9 N2 C8 N1 176.68(16) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C10 C9 C14 C13 0.1(2) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C12 C13 C14 C9 0.7(3) . . . . ?
C14 C9 C10 C11 -0.7(2) . . . . ?

_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_bww17302
_database_code_depnum_ccdc_archive 'CCDC 1572106'
_audit_update_record             
;
2017-11-17 deposited with the CCDC.
2018-04-19 downloaded from the CCDC.
;
_audit_creation_date             2017-06-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H14 N2 O2'
_chemical_formula_sum            'C19 H14 N2 O2'
_chemical_formula_weight         302.32
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.351(2)
_cell_length_b                   11.378(2)
_cell_length_c                   12.992(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.17(3)
_cell_angle_gamma                90
_cell_volume                     1469.6(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4971
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4778
_cell_measurement_theta_min      1.7898
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9576
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_min         2.721
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3105
_reflns_number_total             3338
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0553
_refine_ls_restrained_S_all      1.143
_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)+(0.0500P)²+0.6240P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1266
_refine_ls_wR_factor_ref         0.1302
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.53917(10) 0.50463(9) 0.69231(8) 0.0228(2) Uani 1 1 d . . . . .
O2 O 0.06093(11) 0.53948(11) 0.31804(9) 0.0306(3) Uani 1 1 d . . . . .
N1 N 0.23791(12) 0.49858(10) 0.46335(9) 0.0198(3) Uani 1 1 d . . . . .
N2 N 0.41069(12) 0.63713(11) 0.53487(9) 0.0205(3) Uani 1 1 d . . . . .
C1 C 0.22565(15) 0.68849(13) 0.37859(11) 0.0218(3) Uani 1 1 d . . . . .
C2 C 0.16406(17) 0.77085(14) 0.29966(13) 0.0277(3) Uani 1 1 d . . . . .
H2 H 0.0793 0.7538 0.2505 0.033 Uiso 1 1 calc R . . . .
C3 C 0.22664(17) 0.87609(14) 0.29374(13) 0.0292(4) Uani 1 1 d . . . . .
H3 H 0.1853 0.9320 0.2404 0.035 Uiso 1 1 calc R . . . .
C4 C 0.35202(17) 0.90090(14) 0.36674(13) 0.0266(3) Uani 1 1 d . . . . .
H4 H 0.3957 0.9731 0.3614 0.032 Uiso 1 1 calc R . . . .
C5 C 0.41231(16) 0.82186(13) 0.44586(12) 0.0234(3) Uani 1 1 d . . . . .
H5 H 0.4964 0.8402 0.4953 0.028 Uiso 1 1 calc R . . . .
C6 C 0.34902(15) 0.71388(13) 0.45332(11) 0.0201(3) Uani 1 1 d . . . . .
C7 C 0.35562(14) 0.53523(13) 0.53847(11) 0.0189(3) Uani 1 1 d . . . . .
C8 C 0.16500(15) 0.57349(13) 0.38130(12) 0.0223(3) Uani 1 1 d . . . . .
C9 C 0.18982(15) 0.37834(13) 0.45587(12) 0.0220(3) Uani 1 1 d . . . . .
C10 C 0.09476(16) 0.34490(15) 0.50639(13) 0.0285(4) Uani 1 1 d . . . . .
H10 H 0.0609 0.4000 0.5474 0.034 Uiso 1 1 calc R . . . .
C11 C 0.04923(17) 0.22935(16) 0.49634(15) 0.0344(4) Uani 1 1 d . . . . .
H11 H -0.0147 0.2046 0.5320 0.041 Uiso 1 1 calc R . . . .
C12 C 0.09681(17) 0.15036(15) 0.43460(15) 0.0345(4) Uani 1 1 d . . . . .
H12 H 0.0649 0.0717 0.4274 0.041 Uiso 1 1 calc R . . . .
C13 C 0.19054(17) 0.18567(15) 0.38342(14) 0.0322(4) Uani 1 1 d . . . . .
H13 H 0.2223 0.1313 0.3405 0.039 Uiso 1 1 calc R . . . .
C14 C 0.23874(16) 0.30044(14) 0.39430(12) 0.0257(3) Uani 1 1 d . . . . .
H14 H 0.3042 0.3248 0.3600 0.031 Uiso 1 1 calc R . . . .
C15 C 0.42141(14) 0.45777(13) 0.62766(11) 0.0197(3) Uani 1 1 d . . . . .
C16 C 0.39936(16) 0.35126(13) 0.66750(12) 0.0240(3) Uani 1 1 d . . . . .
H16 H 0.3258 0.3001 0.6382 0.029 Uiso 1 1 calc R . . . .
C17 C 0.50708(17) 0.33104(14) 0.76110(12) 0.0256(3) Uani 1 1 d . . . . .
H17 H 0.5189 0.2642 0.8066 0.031 Uiso 1 1 calc R . . . .
C18 C 0.58946(15) 0.42531(14) 0.77286(11) 0.0236(3) Uani 1 1 d . . . . .
C19 C 0.71602(17) 0.46038(17) 0.85308(13) 0.0334(4) Uani 1 1 d . . . . .
H19A H 0.7848 0.4780 0.8166 0.050 Uiso 1 1 calc GR . . . .
H19B H 0.7472 0.3960 0.9040 0.050 Uiso 1 1 calc GR . . . .
H19C H 0.6997 0.5303 0.8916 0.050 Uiso 1 1 calc GR . . . .


_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 C15 1.3803(17) . ?
O1 C18 1.3701(17) . ?
O2 C8 1.2217(18) . ?
N1 C7 1.3958(18) . ?
N1 C8 1.4087(18) . ?
N1 C9 1.4499(19) . ?
N2 C6 1.3841(18) . ?
N2 C7 1.2986(19) . ?
C1 C2 1.404(2) . ?
C1 C6 1.402(2) . ?
C1 C8 1.456(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.374(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.406(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.408(2) . ?
C7 C15 1.464(2) . ?
C9 C10 1.380(2) . ?
C9 C14 1.381(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.391(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.362(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.421(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.352(2) . ?
C18 C19 1.484(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C18 O1 C15 107.07(12) . . ?
C7 N1 C8 121.84(12) . . ?
C7 N1 C9 123.05(12) . . ?
C8 N1 C9 114.75(12) . . ?
C7 N2 C6 118.51(12) . . ?
C2 C1 C8 120.42(14) . . ?
C6 C1 C2 120.59(14) . . ?
C6 C1 C8 118.95(13) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.82(15) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.88(14) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.89(15) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.88(14) . . ?
C6 C5 H5 120.1 . . ?
N2 C6 C1 122.48(13) . . ?
N2 C6 C5 118.61(13) . . ?
C1 C6 C5 118.91(13) . . ?
N1 C7 C15 119.77(13) . . ?
N2 C7 N1 123.23(13) . . ?
N2 C7 C15 116.99(13) . . ?
O2 C8 N1 120.24(14) . . ?
O2 C8 C1 125.01(14) . . ?
N1 C8 C1 114.73(12) . . ?
C10 C9 N1 120.35(14) . . ?
C10 C9 C14 121.58(15) . . ?
C14 C9 N1 118.04(14) . . ?
C9 C10 H10 120.5 . . ?
C9 C10 C11 118.94(16) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.18(17) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.12(16) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.32(17) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 118.84(16) . . ?
C9 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
O1 C15 C7 112.73(12) . . ?
C16 C15 O1 109.00(12) . . ?
C16 C15 C7 138.27(14) . . ?
C15 C16 H16 126.4 . . ?
C15 C16 C17 107.14(14) . . ?
C17 C16 H16 126.4 . . ?
C16 C17 H17 126.6 . . ?
C18 C17 C16 106.74(14) . . ?
C18 C17 H17 126.6 . . ?
O1 C18 C19 115.63(14) . . ?
C17 C18 O1 110.05(13) . . ?
C17 C18 C19 134.30(15) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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 C15 C16 C17 0.37(17) . . . . ?
N1 C7 C15 O1 177.60(12) . . . . ?
N1 C7 C15 C16 -3.6(3) . . . . ?
N1 C9 C10 C11 179.05(14) . . . . ?
N1 C9 C14 C13 -177.98(13) . . . . ?
N2 C7 C15 O1 -3.40(19) . . . . ?
N2 C7 C15 C16 175.44(17) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C1 C6 N2 177.49(14) . . . . ?
C2 C1 C6 C5 -2.0(2) . . . . ?
C2 C1 C8 O2 0.5(2) . . . . ?
C2 C1 C8 N1 179.05(13) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C3 C4 C5 C6 0.9(2) . . . . ?
C4 C5 C6 N2 -178.78(13) . . . . ?
C4 C5 C6 C1 0.7(2) . . . . ?
C6 N2 C7 N1 0.8(2) . . . . ?
C6 N2 C7 C15 -178.21(12) . . . . ?
C6 C1 C2 C3 1.7(2) . . . . ?
C6 C1 C8 O2 -176.98(15) . . . . ?
C6 C1 C8 N1 1.5(2) . . . . ?
C7 N1 C8 O2 -178.59(14) . . . . ?
C7 N1 C8 C1 2.8(2) . . . . ?
C7 N1 C9 C10 95.84(17) . . . . ?
C7 N1 C9 C14 -86.19(17) . . . . ?
C7 N2 C6 C1 3.9(2) . . . . ?
C7 N2 C6 C5 -176.64(13) . . . . ?
C7 C15 C16 C17 -178.50(17) . . . . ?
C8 N1 C7 N2 -4.2(2) . . . . ?
C8 N1 C7 C15 174.72(13) . . . . ?
C8 N1 C9 C10 -90.91(17) . . . . ?
C8 N1 C9 C14 87.06(16) . . . . ?
C8 C1 C2 C3 -175.82(15) . . . . ?
C8 C1 C6 N2 -5.0(2) . . . . ?
C8 C1 C6 C5 175.52(13) . . . . ?
C9 N1 C7 N2 168.57(14) . . . . ?
C9 N1 C7 C15 -12.5(2) . . . . ?
C9 N1 C8 O2 8.1(2) . . . . ?
C9 N1 C8 C1 -170.51(13) . . . . ?
C9 C10 C11 C12 -1.4(2) . . . . ?
C10 C9 C14 C13 0.0(2) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C13 C14 C9 -0.9(2) . . . . ?
C14 C9 C10 C11 1.1(2) . . . . ?
C15 O1 C18 C17 -0.30(17) . . . . ?
C15 O1 C18 C19 -178.94(13) . . . . ?
C15 C16 C17 C18 -0.55(18) . . . . ?
C16 C17 C18 O1 0.52(18) . . . . ?
C16 C17 C18 C19 178.81(17) . . . . ?
C18 O1 C15 C7 179.12(12) . . . . ?
C18 O1 C15 C16 -0.06(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
